
data_1a

_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H27 N O2 S'
_chemical_formula_sum             'C22 H27 N O2 S'
_chemical_formula_weight          369.50

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    6.334(6)
_cell_length_b                    9.919(8)
_cell_length_c                    16.374(16)
_cell_angle_alpha                 89.62(3)
_cell_angle_beta                  88.65(3)
_cell_angle_gamma                 75.52(2)
_cell_volume                      995.8(16)
_cell_formula_units_Z             2
_cell_measurement_temperature     100

_cell_measurement_reflns_used     3530

_cell_measurement_theta_min       2.5

_cell_measurement_theta_max       31.4


_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.232
_exptl_crystal_F_000              396
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.09

_exptl_crystal_size_mid           0.08

_exptl_crystal_size_min           0.05

_exptl_absorpt_coefficient_mu     0.178
_shelx_estimated_absorpt_T_min    0.984
_shelx_estimated_absorpt_T_max    0.991
_exptl_absorpt_correction_type    Multi-scan

_exptl_absorpt_correction_T_min   0.567

_exptl_absorpt_correction_T_max   1.000

_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)'

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100

_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating Anode'
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method        'profile data from ω-scans'

_diffrn_detector_area_resol_mean  28.5714

_diffrn_reflns_number             13987
_diffrn_reflns_av_unetI/netI      0.1379
_diffrn_reflns_av_R_equivalents   0.0905
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          1.244
_diffrn_reflns_theta_max          31.404
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.885
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.885
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.885
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              5818
_reflns_number_gt                 3276
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution     'SIR2014 (Burla, et al., 2014)'

_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0961P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr

_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5818
_refine_ls_number_parameters      238
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1455
_refine_ls_R_factor_gt            0.0753
_refine_ls_wR_factor_ref          0.2375
_refine_ls_wR_factor_gt           0.1651
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_restrained_S_all       1.049
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.1013(4) 0.7933(3) 0.31808(15) 0.0188(6) Uani 1 1 d . . . . .
C1 C 0.3120(5) 0.8061(3) 0.34647(18) 0.0190(6) Uani 1 1 d . . . . .
H1 H 0.4275 0.7647 0.3048 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3645(5) 0.7277(3) 0.42762(18) 0.0190(6) Uani 1 1 d . . . . .
H2 H 0.5010 0.7441 0.4488 0.023 Uiso 1 1 calc R U . . .
H2A H 0.3893 0.6265 0.4176 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1805(5) 0.7731(3) 0.49276(17) 0.0178(6) Uani 1 1 d . . . . .
H3 H 0.1648 0.8740 0.5046 0.021 Uiso 1 1 calc R U . . .
C4 C -0.0347(5) 0.7584(4) 0.45709(19) 0.0226(7) Uani 1 1 d . . . . .
H4 H -0.0264 0.6586 0.4482 0.027 Uiso 1 1 calc R U . . .
H4A H -0.1554 0.7951 0.4968 0.027 Uiso 1 1 calc R U . . .
C5 C -0.0833(5) 0.8366(4) 0.37649(18) 0.0210(7) Uani 1 1 d . . . . .
H5 H -0.2157 0.8180 0.3530 0.025 Uiso 1 1 calc R U . . .
H5A H -0.1120 0.9380 0.3865 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2427(5) 0.6920(3) 0.57197(18) 0.0193(6) Uani 1 1 d . . . . .
C7 C 0.4241(5) 0.7086(3) 0.61427(19) 0.0226(7) Uani 1 1 d . . . . .
H7 H 0.5045 0.7709 0.5936 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4884(6) 0.6357(4) 0.6858(2) 0.0267(7) Uani 1 1 d . . . . .
H8 H 0.6120 0.6484 0.7136 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3727(6) 0.5445(3) 0.7167(2) 0.0279(8) Uani 1 1 d . . . . .
H9 H 0.4175 0.4935 0.7653 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1897(6) 0.5283(3) 0.6758(2) 0.0268(8) Uani 1 1 d . . . . .
H10 H 0.1086 0.4668 0.6970 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1254(5) 0.6014(3) 0.60433(19) 0.0224(7) Uani 1 1 d . . . . .
H11 H 0.0003 0.5898 0.5771 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0605(5) 0.7674(3) 0.23881(18) 0.0180(6) Uani 1 1 d . . . . .
O1 O -0.1201(3) 0.7674(2) 0.21429(13) 0.0231(5) Uani 1 1 d . . . . .
O2 O 0.2464(3) 0.7354(2) 0.19266(12) 0.0200(5) Uani 1 1 d . . . . .
S1 S 0.31478(14) 0.99038(9) 0.36438(5) 0.0231(2) Uani 1 1 d . . . . .
C13 C 0.2338(5) 0.7153(3) 0.10340(18) 0.0206(7) Uani 1 1 d . . . . .
C14 C 0.4719(5) 0.6918(4) 0.0755(2) 0.0293(8) Uani 1 1 d . . . . .
H14 H 0.5259 0.7724 0.0907 0.044 Uiso 1 1 calc R U . . .
H14A H 0.4833 0.6799 0.0160 0.044 Uiso 1 1 calc R U . . .
H14B H 0.5595 0.6080 0.1018 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1499(6) 0.5872(4) 0.0865(2) 0.0298(8) Uani 1 1 d . . . . .
H15 H 0.2350 0.5077 0.1172 0.045 Uiso 1 1 calc R U . . .
H15A H 0.1648 0.5662 0.0280 0.045 Uiso 1 1 calc R U . . .
H15B H -0.0040 0.6054 0.1035 0.045 Uiso 1 1 calc R U . . .
C16 C 0.0972(6) 0.8480(4) 0.0647(2) 0.0283(8) Uani 1 1 d . . . . .
H16 H -0.0572 0.8579 0.0788 0.042 Uiso 1 1 calc R U . . .
H16A H 0.1180 0.8426 0.0052 0.042 Uiso 1 1 calc R U . . .
H16B H 0.1430 0.9285 0.0853 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2842(5) 1.0617(3) 0.26418(19) 0.0213(7) Uani 1 1 d . . . . .
C18 C 0.4630(5) 1.0443(4) 0.2103(2) 0.0251(7) Uani 1 1 d . . . . .
H18 H 0.6006 0.9871 0.2253 0.030 Uiso 1 1 calc R U . . .
C19 C 0.4398(6) 1.1108(4) 0.1348(2) 0.0287(8) Uani 1 1 d . . . . .
H19 H 0.5621 1.0992 0.0985 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2389(6) 1.1941(3) 0.1122(2) 0.0264(7) Uani 1 1 d . . . . .
H20 H 0.2242 1.2398 0.0607 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0596(6) 1.2104(4) 0.1650(2) 0.0262(7) Uani 1 1 d . . . . .
H21 H -0.0780 1.2670 0.1495 0.031 Uiso 1 1 calc R U . . .
C22 C 0.0808(5) 1.1440(3) 0.2405(2) 0.0240(7) Uani 1 1 d . . . . .
H22 H -0.0426 1.1545 0.2762 0.029 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C12 1.368(4) . ?
N1 C1 1.459(4) . ?
N1 C5 1.472(4) . ?
C1 C2 1.536(4) . ?
C1 S1 1.858(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.544(4) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C6 1.529(4) . ?
C3 C4 1.536(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.524(4) . ?
C4 H4 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C11 1.396(4) . ?
C6 C7 1.400(4) . ?
C7 C8 1.387(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O1 1.221(4) . ?
C12 O2 1.354(4) . ?
O2 C13 1.483(4) . ?
S1 C17 1.778(4) . ?
C13 C15 1.524(5) . ?
C13 C16 1.525(5) . ?
C13 C14 1.527(5) . ?
C14 H14 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.395(4) . ?
C17 C22 1.404(5) . ?
C18 C19 1.391(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C12 N1 C1 124.1(2) . . ?
C12 N1 C5 119.1(2) . . ?
C1 N1 C5 115.8(2) . . ?
N1 C1 C2 109.8(2) . . ?
N1 C1 S1 112.0(2) . . ?
C2 C1 S1 107.5(2) . . ?
N1 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
S1 C1 H1 109.1 . . ?
C1 C2 C3 112.7(3) . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
H2 C2 H2A 107.8 . . ?
C6 C3 C4 114.2(2) . . ?
C6 C3 C2 110.1(3) . . ?
C4 C3 C2 108.9(2) . . ?
C6 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C5 C4 C3 111.8(2) . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
H4 C4 H4A 107.9 . . ?
N1 C5 C4 110.8(3) . . ?
N1 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
H5 C5 H5A 108.1 . . ?
C11 C6 C7 118.2(3) . . ?
C11 C6 C3 122.6(3) . . ?
C7 C6 C3 119.1(3) . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
O1 C12 O2 124.8(3) . . ?
O1 C12 N1 123.7(3) . . ?
O2 C12 N1 111.4(3) . . ?
C12 O2 C13 119.4(2) . . ?
C17 S1 C1 102.28(15) . . ?
O2 C13 C15 110.3(2) . . ?
O2 C13 C16 109.9(3) . . ?
C15 C13 C16 113.3(3) . . ?
O2 C13 C14 102.1(2) . . ?
C15 C13 C14 110.8(3) . . ?
C16 C13 C14 109.9(3) . . ?
C13 C14 H14 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C15 H15 109.5 . . ?
C13 C15 H15A 109.5 . . ?
H15 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C16 H16 109.5 . . ?
C13 C16 H16A 109.5 . . ?
H16 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C18 C17 C22 119.3(3) . . ?
C18 C17 S1 120.9(3) . . ?
C22 C17 S1 119.7(2) . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C12 N1 C1 C2 -137.0(3) . . . . ?
C5 N1 C1 C2 54.4(4) . . . . ?
C12 N1 C1 S1 103.6(3) . . . . ?
C5 N1 C1 S1 -65.0(3) . . . . ?
N1 C1 C2 C3 -53.6(3) . . . . ?
S1 C1 C2 C3 68.5(3) . . . . ?
C1 C2 C3 C6 -179.8(2) . . . . ?
C1 C2 C3 C4 54.3(3) . . . . ?
C6 C3 C4 C5 -177.7(3) . . . . ?
C2 C3 C4 C5 -54.1(3) . . . . ?
C12 N1 C5 C4 135.5(3) . . . . ?
C1 N1 C5 C4 -55.3(4) . . . . ?
C3 C4 C5 N1 54.1(4) . . . . ?
C4 C3 C6 C11 6.2(4) . . . . ?
C2 C3 C6 C11 -116.7(3) . . . . ?
C4 C3 C6 C7 -173.7(3) . . . . ?
C2 C3 C6 C7 63.4(4) . . . . ?
C11 C6 C7 C8 1.0(5) . . . . ?
C3 C6 C7 C8 -179.1(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C6 0.2(5) . . . . ?
C7 C6 C11 C10 -1.1(5) . . . . ?
C3 C6 C11 C10 179.0(3) . . . . ?
C1 N1 C12 O1 -174.2(3) . . . . ?
C5 N1 C12 O1 -6.0(5) . . . . ?
C1 N1 C12 O2 8.8(4) . . . . ?
C5 N1 C12 O2 177.0(3) . . . . ?
O1 C12 O2 C13 8.1(5) . . . . ?
N1 C12 O2 C13 -175.0(2) . . . . ?
N1 C1 S1 C17 -65.8(2) . . . . ?
C2 C1 S1 C17 173.4(2) . . . . ?
C12 O2 C13 C15 -65.9(4) . . . . ?
C12 O2 C13 C16 59.7(3) . . . . ?
C12 O2 C13 C14 176.3(3) . . . . ?
C1 S1 C17 C18 -81.5(3) . . . . ?
C1 S1 C17 C22 102.6(3) . . . . ?
C22 C17 C18 C19 1.4(5) . . . . ?
S1 C17 C18 C19 -174.5(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C19 C20 C21 C22 0.2(5) . . . . ?
C20 C21 C22 C17 0.8(5) . . . . ?
C18 C17 C22 C21 -1.6(5) . . . . ?
S1 C17 C22 C21 174.3(3) . . . . ?

_refine_diff_density_max    0.429
_refine_diff_density_min   -0.578
_refine_diff_density_rms    0.140



_publ_section_references
;
    Burla, M. C.; Caliandro, R.; Carrozzini, B.; Cascarano, G. L.; Cuocci, C.;
    Giacovazzo, C.; Mallamo, M.; Mazzone, A.; Polidori, G. (2015), Appl. Cryst.
    48, 306-309.

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

    Rigaku (1998). REQAB. 
    Rigaku Corporation, Tokyo, Japan.

    Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
    Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
    Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn.,
    51, 218-224.
;
_chemical_absolute_configuration  ?


data_1b

_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H25 N O2 S'
_chemical_formula_sum             'C17 H25 N O2 S'
_chemical_formula_weight          307.44

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    10.541(4)
_cell_length_b                    16.901(6)
_cell_length_c                    18.710(6)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3333(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     100

_cell_measurement_reflns_used     10510

_cell_measurement_theta_min       2.2

_cell_measurement_theta_max       31.2


_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.225
_exptl_crystal_F_000              1328
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.199
_shelx_estimated_absorpt_T_min    0.961
_shelx_estimated_absorpt_T_max    0.961
_exptl_absorpt_correction_type    Multi-scan

_exptl_absorpt_correction_T_min   0.658

_exptl_absorpt_correction_T_max   1.000

_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)'

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating Anode'
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method        'profile data from ω-scans'

_diffrn_detector_area_resol_mean  28.5714

_diffrn_reflns_number             12485
_diffrn_reflns_av_unetI/netI      0.0453
_diffrn_reflns_av_R_equivalents   0.0451
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.177
_diffrn_reflns_theta_max          27.495
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.974
_diffrn_measured_fraction_theta_full  0.983
_diffrn_reflns_Laue_measured_fraction_max    0.974
_diffrn_reflns_Laue_measured_fraction_full   0.983
_diffrn_reflns_point_group_measured_fraction_max   0.974
_diffrn_reflns_point_group_measured_fraction_full  0.983
_reflns_number_total              3720
_reflns_number_gt                 3151
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution     'SHELXT-2017/1 (Sheldrick, 2017)'

_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0570P)²+1.4391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?

_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3720
_refine_ls_number_parameters      194
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0686
_refine_ls_R_factor_gt            0.0564
_refine_ls_wR_factor_ref          0.1421
_refine_ls_wR_factor_gt           0.1343
_refine_ls_goodness_of_fit_ref    1.161
_refine_ls_restrained_S_all       1.161
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.29075(15) 0.62242(10) 0.61889(8) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.17834(19) 0.58263(12) 0.59269(10) 0.0231(4) Uani 1 1 d . . . . .
H1 H 0.129027 0.564160 0.635188 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0938(2) 0.64022(13) 0.55090(11) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.050330 0.675294 0.585503 0.033 Uiso 1 1 calc R U . . .
H2A H 0.027568 0.609261 0.525866 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1627(2) 0.69234(13) 0.49547(11) 0.0284(5) Uani 1 1 d . . . . .
H3 H 0.105443 0.737866 0.484257 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2845(2) 0.72672(13) 0.52799(11) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.335069 0.751796 0.489604 0.033 Uiso 1 1 calc R U . . .
H4A H 0.261404 0.768410 0.562821 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3657(2) 0.66472(13) 0.56541(11) 0.0263(5) Uani 1 1 d . . . . .
H5 H 0.398891 0.626720 0.529751 0.032 Uiso 1 1 calc R U . . .
H5A H 0.438820 0.690749 0.588827 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1875(2) 0.64864(14) 0.42559(12) 0.0344(5) Uani 1 1 d . . . . .
H6 H 0.222097 0.685614 0.390275 0.052 Uiso 1 1 calc R U . . .
H6A H 0.107774 0.626350 0.407642 0.052 Uiso 1 1 calc R U . . .
H6B H 0.248460 0.605868 0.433936 0.052 Uiso 1 1 calc R U . . .
C7 C 0.32110(18) 0.62882(12) 0.68951(10) 0.0202(4) Uani 1 1 d . . . . .
O1 O 0.41210(13) 0.66594(8) 0.71192(7) 0.0255(3) Uani 1 1 d . . . . .
S1 S 0.21608(6) 0.49469(3) 0.53799(3) 0.03171(18) Uani 1 1 d . . . . .
O2 O 0.23680(13) 0.58910(8) 0.73047(7) 0.0220(3) Uani 1 1 d . . . . .
C8 C 0.26143(19) 0.57706(12) 0.80751(10) 0.0217(4) Uani 1 1 d . . . . .
C9 C 0.2576(2) 0.65611(13) 0.84652(11) 0.0307(5) Uani 1 1 d . . . . .
H9 H 0.330734 0.688187 0.832217 0.046 Uiso 1 1 calc R U . . .
H9A H 0.260365 0.646936 0.898215 0.046 Uiso 1 1 calc R U . . .
H9B H 0.179099 0.684081 0.834231 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3859(2) 0.53317(14) 0.81711(11) 0.0284(5) Uani 1 1 d . . . . .
H10 H 0.383655 0.483802 0.789663 0.043 Uiso 1 1 calc R U . . .
H10A H 0.398474 0.521090 0.867841 0.043 Uiso 1 1 calc R U . . .
H10B H 0.455917 0.566287 0.800004 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1493(2) 0.52661(13) 0.83049(10) 0.0260(4) Uani 1 1 d . . . . .
H11 H 0.070197 0.554947 0.820416 0.039 Uiso 1 1 calc R U . . .
H11A H 0.155161 0.515780 0.881841 0.039 Uiso 1 1 calc R U . . .
H11B H 0.150275 0.476573 0.804033 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2781(2) 0.42935(12) 0.60397(11) 0.0255(4) Uani 1 1 d . . . . .
C13 C 0.4041(2) 0.40625(13) 0.60018(12) 0.0316(5) Uani 1 1 d . . . . .
H13 H 0.458077 0.428944 0.565074 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4521(2) 0.35021(14) 0.64725(13) 0.0375(6) Uani 1 1 d . . . . .
H14 H 0.538100 0.333982 0.643536 0.045 Uiso 1 1 calc R U . . .
C15 C 0.3750(2) 0.31793(14) 0.69954(12) 0.0356(5) Uani 1 1 d . . . . .
H15 H 0.407983 0.279763 0.731842 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2490(2) 0.34165(14) 0.70455(12) 0.0339(5) Uani 1 1 d . . . . .
H16 H 0.196072 0.320047 0.740704 0.041 Uiso 1 1 calc R U . . .
C17 C 0.2004(2) 0.39676(13) 0.65692(11) 0.0286(5) Uani 1 1 d . . . . .
H17 H 0.114079 0.412410 0.660288 0.034 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C7 1.364(2) . ?
N1 C1 1.448(3) . ?
N1 C5 1.461(2) . ?
C1 C2 1.534(3) . ?
C1 S1 1.848(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.543(3) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C6 1.524(3) . ?
C3 C4 1.535(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.524(3) . ?
C4 H4 0.9900 . ?
C4 H4A 0.9900 . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 H6 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 O1 1.220(2) . ?
C7 O2 1.352(2) . ?
S1 C12 1.781(2) . ?
O2 C8 1.479(2) . ?
C8 C10 1.518(3) . ?
C8 C11 1.519(3) . ?
C8 C9 1.523(3) . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.386(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C7 N1 C1 123.83(16) . . ?
C7 N1 C5 119.85(17) . . ?
C1 N1 C5 115.95(16) . . ?
N1 C1 C2 110.70(17) . . ?
N1 C1 S1 112.64(14) . . ?
C2 C1 S1 110.68(14) . . ?
N1 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
S1 C1 H1 107.5 . . ?
C1 C2 C3 115.55(18) . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
H2 C2 H2A 107.5 . . ?
C6 C3 C4 112.34(19) . . ?
C6 C3 C2 112.39(18) . . ?
C4 C3 C2 110.09(17) . . ?
C6 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C2 C3 H3 107.2 . . ?
C5 C4 C3 113.06(18) . . ?
C5 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
H4 C4 H4A 107.8 . . ?
N1 C5 C4 110.33(17) . . ?
N1 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
H5 C5 H5A 108.1 . . ?
C3 C6 H6 109.5 . . ?
C3 C6 H6A 109.5 . . ?
H6 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C7 O2 125.26(18) . . ?
O1 C7 N1 123.91(18) . . ?
O2 C7 N1 110.83(16) . . ?
C12 S1 C1 101.18(10) . . ?
C7 O2 C8 120.36(15) . . ?
O2 C8 C10 109.53(16) . . ?
O2 C8 C11 102.50(15) . . ?
C10 C8 C11 111.39(17) . . ?
O2 C8 C9 109.98(16) . . ?
C10 C8 C9 113.28(17) . . ?
C11 C8 C9 109.63(17) . . ?
C8 C9 H9 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C10 H10 109.5 . . ?
C8 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C11 H11 109.5 . . ?
C8 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 S1 119.39(17) . . ?
C17 C12 S1 121.39(17) . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C7 N1 C1 C2 119.5(2) . . . . ?
C5 N1 C1 C2 -53.5(2) . . . . ?
C7 N1 C1 S1 -115.95(18) . . . . ?
C5 N1 C1 S1 71.0(2) . . . . ?
N1 C1 C2 C3 47.0(2) . . . . ?
S1 C1 C2 C3 -78.6(2) . . . . ?
C1 C2 C3 C6 80.7(2) . . . . ?
C1 C2 C3 C4 -45.3(2) . . . . ?
C6 C3 C4 C5 -77.5(2) . . . . ?
C2 C3 C4 C5 48.6(2) . . . . ?
C7 N1 C5 C4 -115.5(2) . . . . ?
C1 N1 C5 C4 57.9(2) . . . . ?
C3 C4 C5 N1 -54.4(2) . . . . ?
C1 N1 C7 O1 -175.90(19) . . . . ?
C5 N1 C7 O1 -3.1(3) . . . . ?
C1 N1 C7 O2 3.8(3) . . . . ?
C5 N1 C7 O2 176.59(17) . . . . ?
N1 C1 S1 C12 69.20(16) . . . . ?
C2 C1 S1 C12 -166.28(14) . . . . ?
O1 C7 O2 C8 -10.0(3) . . . . ?
N1 C7 O2 C8 170.32(16) . . . . ?
C7 O2 C8 C10 -58.3(2) . . . . ?
C7 O2 C8 C11 -176.64(16) . . . . ?
C7 O2 C8 C9 66.8(2) . . . . ?
C1 S1 C12 C13 -115.36(18) . . . . ?
C1 S1 C12 C17 68.83(19) . . . . ?
C17 C12 C13 C14 1.4(3) . . . . ?
S1 C12 C13 C14 -174.50(17) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C12 -0.6(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
S1 C12 C17 C16 175.36(17) . . . . ?

_refine_diff_density_max    0.685
_refine_diff_density_min   -0.444
_refine_diff_density_rms    0.068



_publ_section_references
;
    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

    Rigaku (1998). REQAB. 
    Rigaku Corporation, Tokyo, Japan.

    Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
    Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
    Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn.,
    51, 218-224.
;
_chemical_absolute_configuration  ?



data_1d

_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H25 N O2 S'
_chemical_formula_sum             'C17 H25 N O2 S'
_chemical_formula_weight          307.44

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       trigonal
_space_group_IT_number            144
_space_group_name_H-M_alt         'P 31'
_space_group_name_Hall            'P 31'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-y, x-y, z+1/3'
 '-x+y, -x, z+2/3'

_cell_length_a                    10.154(4)
_cell_length_b                    10.154(4)
_cell_length_c                    14.189(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 120
_cell_volume                      1267.0(10)
_cell_formula_units_Z             3
_cell_measurement_temperature     100.1500

_cell_measurement_reflns_used     4357

_cell_measurement_theta_min       3.6901

_cell_measurement_theta_max       27.4353


_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.209
_exptl_crystal_F_000              498
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.5800
_exptl_crystal_size_mid           0.3200
_exptl_crystal_size_min           0.2000

_exptl_absorpt_coefficient_mu     0.196
_shelx_estimated_absorpt_T_min    0.895
_shelx_estimated_absorpt_T_max    0.962
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9041
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100.1500

_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   ?

_diffrn_measurement_method        dtprofit.ref

_diffrn_detector_area_resol_mean  28.5714

_diffrn_reflns_number             20112
_diffrn_reflns_av_unetI/netI      0.0293
_diffrn_reflns_av_R_equivalents   0.0350
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.690
_diffrn_reflns_theta_max          27.437
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              3847
_reflns_number_gt                 3480
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.999
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.997

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection        'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement        'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction         'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution     'SHELXT-2017/1 (Sheldrick, 2017)'

_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr

_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.020(19)
_chemical_absolute_configuration  ad

_refine_ls_number_reflns          3847
_refine_ls_number_parameters      194
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0278
_refine_ls_R_factor_gt            0.0255
_refine_ls_wR_factor_ref          0.0662
_refine_ls_wR_factor_gt           0.0653
_refine_ls_goodness_of_fit_ref    0.987
_refine_ls_restrained_S_all       0.987
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.80984(17) 0.77926(17) 0.53335(11) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.6675(2) 0.7290(2) 0.58314(13) 0.0254(4) Uani 1 1 d . . . . .
H1 H 0.661367 0.661972 0.636633 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6592(2) 0.8647(2) 0.62271(15) 0.0327(4) Uani 1 1 d . . . . .
H2 H 0.555749 0.829096 0.647763 0.039 Uiso 1 1 calc R U . . .
H2A H 0.731976 0.909768 0.675572 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6956(3) 0.9862(3) 0.54816(17) 0.0365(5) Uani 1 1 d . . . . .
H3 H 0.698992 1.075909 0.578142 0.044 Uiso 1 1 calc R U . . .
H3A H 0.613608 0.946172 0.500366 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8482(2) 1.0355(2) 0.49930(15) 0.0325(5) Uani 1 1 d . . . . .
H4 H 0.858017 1.102827 0.445113 0.039 Uiso 1 1 calc R U . . .
C5 C 0.8494(2) 0.8951(2) 0.45990(14) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.775644 0.851534 0.407419 0.033 Uiso 1 1 calc R U . . .
H5A H 0.951737 0.925868 0.434694 0.033 Uiso 1 1 calc R U . . .
C6 C 0.9834(3) 1.1252(3) 0.56510(19) 0.0442(6) Uani 1 1 d . . . . .
H6 H 0.980069 1.059005 0.616437 0.066 Uiso 1 1 calc R U . . .
H6A H 0.978422 1.211841 0.591377 0.066 Uiso 1 1 calc R U . . .
H6B H 1.078269 1.162098 0.529698 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8863(2) 0.7011(2) 0.54936(13) 0.0208(3) Uani 1 1 d . . . . .
O1 O 0.85348(15) 0.60797(15) 0.61145(9) 0.0277(3) Uani 1 1 d . . . . .
S1 S 0.49889(5) 0.62105(5) 0.50565(4) 0.02742(12) Uani 1 1 d . . . . .
O2 O 1.00193(15) 0.74409(15) 0.48798(9) 0.0229(3) Uani 1 1 d . . . . .
C8 C 1.1058(2) 0.6816(2) 0.49667(13) 0.0224(4) Uani 1 1 d . . . . .
C9 C 1.2156(2) 0.7581(3) 0.41528(14) 0.0297(4) Uani 1 1 d . . . . .
H9 H 1.160350 0.723876 0.355471 0.045 Uiso 1 1 calc R U . . .
H9A H 1.295594 0.730985 0.417278 0.045 Uiso 1 1 calc R U . . .
H9B H 1.261464 0.868659 0.420638 0.045 Uiso 1 1 calc R U . . .
C10 C 1.1897(2) 0.7293(3) 0.58986(13) 0.0289(4) Uani 1 1 d . . . . .
H10 H 1.239559 0.840084 0.596291 0.043 Uiso 1 1 calc R U . . .
H10A H 1.266467 0.697784 0.591922 0.043 Uiso 1 1 calc R U . . .
H10B H 1.117324 0.680904 0.641648 0.043 Uiso 1 1 calc R U . . .
C11 C 1.0182(3) 0.5091(2) 0.48408(17) 0.0356(5) Uani 1 1 d . . . . .
H11 H 0.952528 0.461724 0.538894 0.053 Uiso 1 1 calc R U . . .
H11A H 1.090200 0.471858 0.478263 0.053 Uiso 1 1 calc R U . . .
H11B H 0.955739 0.483057 0.427015 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5166(2) 0.4609(2) 0.47411(14) 0.0251(4) Uani 1 1 d . . . . .
C13 C 0.4253(3) 0.3228(2) 0.51788(17) 0.0416(6) Uani 1 1 d . . . . .
H13 H 0.357257 0.314667 0.566469 0.050 Uiso 1 1 calc R U . . .
C14 C 0.4339(4) 0.1960(3) 0.49023(18) 0.0561(7) Uani 1 1 d . . . . .
H14 H 0.370077 0.100693 0.519554 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5343(3) 0.2068(3) 0.42040(16) 0.0395(5) Uani 1 1 d . . . . .
H15 H 0.541333 0.120127 0.403244 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6238(2) 0.3440(2) 0.37604(16) 0.0335(5) Uani 1 1 d . . . . .
H16 H 0.691731 0.352074 0.327405 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6142(2) 0.4705(2) 0.40277(16) 0.0315(5) Uani 1 1 d . . . . .
H17 H 0.675330 0.564825 0.371734 0.038 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C7 1.378(2) . ?
N1 C1 1.452(2) . ?
N1 C5 1.469(2) . ?
C1 C2 1.530(3) . ?
C1 S1 1.862(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.524(3) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.535(3) . ?
C3 H3 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C6 1.528(3) . ?
C4 C5 1.537(3) . ?
C4 H4 1.0000 . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 H6 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 O1 1.211(2) . ?
C7 O2 1.347(2) . ?
S1 C12 1.780(2) . ?
O2 C8 1.483(2) . ?
C8 C10 1.515(3) . ?
C8 C9 1.521(3) . ?
C8 C11 1.527(3) . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.383(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C7 N1 C1 117.70(15) . . ?
C7 N1 C5 124.78(15) . . ?
C1 N1 C5 116.90(15) . . ?
N1 C1 C2 110.82(17) . . ?
N1 C1 S1 112.35(13) . . ?
C2 C1 S1 107.33(13) . . ?
N1 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
S1 C1 H1 108.8 . . ?
C3 C2 C1 111.99(17) . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
H2 C2 H2A 107.9 . . ?
C2 C3 C4 112.00(16) . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
H3 C3 H3A 107.9 . . ?
C6 C4 C3 112.2(2) . . ?
C6 C4 C5 110.68(17) . . ?
C3 C4 C5 109.69(17) . . ?
C6 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
N1 C5 C4 111.02(16) . . ?
N1 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
H5 C5 H5A 108.0 . . ?
C4 C6 H6 109.5 . . ?
C4 C6 H6A 109.5 . . ?
H6 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C7 O2 125.31(16) . . ?
O1 C7 N1 123.74(16) . . ?
O2 C7 N1 110.95(15) . . ?
C12 S1 C1 101.70(9) . . ?
C7 O2 C8 119.93(14) . . ?
O2 C8 C10 110.01(15) . . ?
O2 C8 C9 102.40(14) . . ?
C10 C8 C9 110.38(17) . . ?
O2 C8 C11 110.48(16) . . ?
C10 C8 C11 112.37(17) . . ?
C9 C8 C11 110.77(17) . . ?
C8 C9 H9 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C10 H10 109.5 . . ?
C8 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C11 H11 109.5 . . ?
C8 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C13 C12 C17 119.49(18) . . ?
C13 C12 S1 119.40(16) . . ?
C17 C12 S1 121.01(15) . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 120.9(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C7 N1 C1 C2 135.89(17) . . . . ?
C5 N1 C1 C2 -52.6(2) . . . . ?
C7 N1 C1 S1 -104.05(17) . . . . ?
C5 N1 C1 S1 67.41(19) . . . . ?
N1 C1 C2 C3 50.5(2) . . . . ?
S1 C1 C2 C3 -72.55(19) . . . . ?
C1 C2 C3 C4 -53.3(2) . . . . ?
C2 C3 C4 C6 -69.4(2) . . . . ?
C2 C3 C4 C5 54.0(2) . . . . ?
C7 N1 C5 C4 -134.51(18) . . . . ?
C1 N1 C5 C4 54.7(2) . . . . ?
C6 C4 C5 N1 71.4(2) . . . . ?
C3 C4 C5 N1 -52.9(2) . . . . ?
C1 N1 C7 O1 -10.7(3) . . . . ?
C5 N1 C7 O1 178.59(18) . . . . ?
C1 N1 C7 O2 170.19(15) . . . . ?
C5 N1 C7 O2 -0.5(2) . . . . ?
N1 C1 S1 C12 62.71(15) . . . . ?
C2 C1 S1 C12 -175.23(14) . . . . ?
O1 C7 O2 C8 -3.2(3) . . . . ?
N1 C7 O2 C8 175.92(15) . . . . ?
C7 O2 C8 C10 -62.8(2) . . . . ?
C7 O2 C8 C9 179.80(15) . . . . ?
C7 O2 C8 C11 61.8(2) . . . . ?
C1 S1 C12 C13 102.53(18) . . . . ?
C1 S1 C12 C17 -81.13(18) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
S1 C12 C13 C14 177.0(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C13 C12 C17 C16 -1.4(3) . . . . ?
S1 C12 C17 C16 -177.69(16) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?

_refine_diff_density_max    0.160
_refine_diff_density_min   -0.137
_refine_diff_density_rms    0.031



_publ_section_references
;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009).
J. Cryst. Soc.  Jpn. 51, 218-224.
;



data_1e

_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H27 N O2 S'
_chemical_formula_sum             'C22 H27 N O2 S'
_chemical_formula_weight          369.50

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    10.555(2)
_cell_length_b                    21.275(4)
_cell_length_c                    17.615(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3955.6(13)
_cell_formula_units_Z             8
_cell_measurement_temperature     110

_cell_measurement_reflns_used     11373

_cell_measurement_theta_min       2.2

_cell_measurement_theta_max       31.2


_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.241
_exptl_crystal_F_000              1584
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.22

_exptl_crystal_size_mid           0.18

_exptl_crystal_size_min           0.13

_exptl_absorpt_coefficient_mu     0.179
_shelx_estimated_absorpt_T_min    0.962
_shelx_estimated_absorpt_T_max    0.977
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.889
_exptl_absorpt_correction_T_max   1.000

_exptl_absorpt_process_details    ?

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       110

_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating Anode'
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method        'profile data from ω-scans'

_diffrn_detector_area_resol_mean  28.5714

_diffrn_reflns_number             60370
_diffrn_reflns_av_unetI/netI      0.0215
_diffrn_reflns_av_R_equivalents   0.0541
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          1.914
_diffrn_reflns_theta_max          27.500
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4540
_reflns_number_gt                 4378
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution     'SHELXT-2017/1 (Sheldrick, 2017)'

_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0802P)²+1.1287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr

_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4540
_refine_ls_number_parameters      238
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0581
_refine_ls_R_factor_gt            0.0500
_refine_ls_wR_factor_ref          0.1601
_refine_ls_wR_factor_gt           0.1426
_refine_ls_goodness_of_fit_ref    1.300
_refine_ls_restrained_S_all       1.300
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.55092(13) 0.34086(7) 0.66736(8) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.58590(16) 0.29693(8) 0.72716(10) 0.0201(4) Uani 1 1 d . . . . .
H1 H 0.516831 0.264904 0.730812 0.024 Uiso 1 1 calc R U . . .
C2 C 0.59630(18) 0.32888(9) 0.80431(10) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.635108 0.299414 0.841074 0.030 Uiso 1 1 calc R U . . .
H2A H 0.510421 0.339571 0.822854 0.030 Uiso 1 1 calc R U . . .
C3 C 0.67603(19) 0.38847(9) 0.80000(10) 0.0267(4) Uani 1 1 d . . . . .
H3 H 0.680467 0.408736 0.850523 0.032 Uiso 1 1 calc R U . . .
H3A H 0.763250 0.378155 0.783515 0.032 Uiso 1 1 calc R U . . .
C4 C 0.61395(18) 0.43263(9) 0.74307(11) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.662439 0.472434 0.741195 0.031 Uiso 1 1 calc R U . . .
H4A H 0.527027 0.442580 0.760425 0.031 Uiso 1 1 calc R U . . .
C5 C 0.60764(16) 0.40440(8) 0.66319(10) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.547221 0.431023 0.633557 0.025 Uiso 1 1 calc R U . . .
C6 C 0.48262(16) 0.31649(8) 0.60781(10) 0.0201(4) Uani 1 1 d . . . . .
O1 O 0.45544(13) 0.26094(6) 0.60193(7) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.44945(13) 0.36184(6) 0.55849(7) 0.0241(3) Uani 1 1 d . . . . .
C7 C 0.38789(18) 0.34609(9) 0.48538(10) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.26092(18) 0.31425(10) 0.49915(11) 0.0291(4) Uani 1 1 d . . . . .
H8 H 0.274837 0.273149 0.522853 0.044 Uiso 1 1 calc R U . . .
H8A H 0.216894 0.308606 0.450642 0.044 Uiso 1 1 calc R U . . .
H8B H 0.209242 0.340462 0.532816 0.044 Uiso 1 1 calc R U . . .
C9 C 0.47866(19) 0.30684(10) 0.43781(11) 0.0296(4) Uani 1 1 d . . . . .
H9 H 0.559484 0.329104 0.432684 0.044 Uiso 1 1 calc R U . . .
H9A H 0.442002 0.299867 0.387392 0.044 Uiso 1 1 calc R U . . .
H9B H 0.492922 0.266264 0.462729 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3688(2) 0.41063(11) 0.45021(13) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.312612 0.435642 0.482622 0.058 Uiso 1 1 calc R U . . .
H10A H 0.330550 0.406011 0.399812 0.058 Uiso 1 1 calc R U . . .
H10B H 0.450793 0.431855 0.445510 0.058 Uiso 1 1 calc R U . . .
C11 C 0.69736(17) 0.17975(8) 0.74595(10) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.60180(18) 0.14326(9) 0.71339(11) 0.0264(4) Uani 1 1 d . . . . .
H12 H 0.557011 0.158309 0.670287 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5723(2) 0.08503(9) 0.74400(12) 0.0305(4) Uani 1 1 d . . . . .
H13 H 0.505554 0.060807 0.722750 0.037 Uiso 1 1 calc R U . . .
C14 C 0.64025(19) 0.06190(9) 0.80581(12) 0.0294(4) Uani 1 1 d . . . . .
H14 H 0.621377 0.021553 0.825971 0.035 Uiso 1 1 calc R U . . .
C15 C 0.73575(19) 0.09823(9) 0.83776(11) 0.0285(4) Uani 1 1 d . . . . .
H15 H 0.782431 0.082542 0.879795 0.034 Uiso 1 1 calc R U . . .
C16 C 0.76350(17) 0.15749(9) 0.80856(11) 0.0247(4) Uani 1 1 d . . . . .
H16 H 0.827455 0.182584 0.831396 0.030 Uiso 1 1 calc R U . . .
C17 C 0.73394(17) 0.40526(8) 0.61958(10) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.81607(18) 0.45631(9) 0.62602(11) 0.0253(4) Uani 1 1 d . . . . .
H18 H 0.796446 0.489186 0.660565 0.030 Uiso 1 1 calc R U . . .
C19 C 0.92608(19) 0.46004(9) 0.58290(12) 0.0304(4) Uani 1 1 d . . . . .
H19 H 0.980983 0.495108 0.588557 0.037 Uiso 1 1 calc R U . . .
C20 C 0.95612(19) 0.41293(10) 0.53175(12) 0.0301(4) Uani 1 1 d . . . . .
H20 H 1.031492 0.415441 0.502430 0.036 Uiso 1 1 calc R U . . .
C21 C 0.87506(19) 0.36201(9) 0.52371(11) 0.0267(4) Uani 1 1 d . . . . .
H21 H 0.894452 0.329625 0.488445 0.032 Uiso 1 1 calc R U . . .
C22 C 0.76509(17) 0.35838(9) 0.56741(10) 0.0234(4) Uani 1 1 d . . . . .
H22 H 0.710305 0.323288 0.561544 0.028 Uiso 1 1 calc R U . . .
S1 S 0.73683(4) 0.25386(2) 0.70527(3) 0.02251(15) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C6 1.374(2) . ?
N1 C1 1.456(2) . ?
N1 C5 1.480(2) . ?
C1 C2 1.523(2) . ?
C1 S1 1.8779(18) . ?
C1 H1 1.0000 . ?
C2 C3 1.524(3) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.522(3) . ?
C3 H3 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.531(2) . ?
C4 H4 0.9900 . ?
C4 H4A 0.9900 . ?
C5 C17 1.539(2) . ?
C5 H5 1.0000 . ?
C6 O1 1.220(2) . ?
C6 O2 1.345(2) . ?
O2 C7 1.481(2) . ?
C7 C10 1.520(3) . ?
C7 C8 1.521(3) . ?
C7 C9 1.522(3) . ?
C8 H8 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C16 1.388(3) . ?
C11 C12 1.396(3) . ?
C11 S1 1.7813(18) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 C22 1.395(3) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 N1 C1 116.30(14) . . ?
C6 N1 C5 121.25(14) . . ?
C1 N1 C5 121.30(14) . . ?
N1 C1 C2 112.17(14) . . ?
N1 C1 S1 112.33(11) . . ?
C2 C1 S1 109.86(12) . . ?
N1 C1 H1 107.4 . . ?
C2 C1 H1 107.4 . . ?
S1 C1 H1 107.4 . . ?
C1 C2 C3 111.50(15) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
H2 C2 H2A 108.0 . . ?
C4 C3 C2 107.98(15) . . ?
C4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
H3 C3 H3A 108.4 . . ?
C3 C4 C5 112.46(15) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
H4 C4 H4A 107.8 . . ?
N1 C5 C4 109.28(14) . . ?
N1 C5 C17 112.71(14) . . ?
C4 C5 C17 114.61(15) . . ?
N1 C5 H5 106.6 . . ?
C4 C5 H5 106.6 . . ?
C17 C5 H5 106.6 . . ?
O1 C6 O2 125.35(16) . . ?
O1 C6 N1 123.60(16) . . ?
O2 C6 N1 111.04(14) . . ?
C6 O2 C7 120.92(14) . . ?
O2 C7 C10 102.03(15) . . ?
O2 C7 C8 110.41(15) . . ?
C10 C7 C8 110.51(17) . . ?
O2 C7 C9 109.06(15) . . ?
C10 C7 C9 110.78(17) . . ?
C8 C7 C9 113.44(16) . . ?
C7 C8 H8 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C9 H9 109.5 . . ?
C7 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C10 H10 109.5 . . ?
C7 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C16 C11 C12 119.99(17) . . ?
C16 C11 S1 120.26(14) . . ?
C12 C11 S1 119.73(14) . . ?
C13 C12 C11 119.95(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.27(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.56(18) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.44(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.76(18) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C22 117.63(17) . . ?
C18 C17 C5 120.49(16) . . ?
C22 C17 C5 121.63(16) . . ?
C19 C18 C17 121.30(18) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.38(18) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.36(18) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 120.00(19) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 121.33(18) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C11 S1 C1 98.68(8) . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 N1 C1 C2 -150.11(15) . . . . ?
C5 N1 C1 C2 42.0(2) . . . . ?
C6 N1 C1 S1 85.56(16) . . . . ?
C5 N1 C1 S1 -82.36(16) . . . . ?
N1 C1 C2 C3 -48.7(2) . . . . ?
S1 C1 C2 C3 76.97(17) . . . . ?
C1 C2 C3 C4 58.9(2) . . . . ?
C2 C3 C4 C5 -61.3(2) . . . . ?
C6 N1 C5 C4 150.28(16) . . . . ?
C1 N1 C5 C4 -42.4(2) . . . . ?
C6 N1 C5 C17 -81.06(19) . . . . ?
C1 N1 C5 C17 86.25(18) . . . . ?
C3 C4 C5 N1 51.1(2) . . . . ?
C3 C4 C5 C17 -76.53(19) . . . . ?
C1 N1 C6 O1 -2.9(2) . . . . ?
C5 N1 C6 O1 165.06(16) . . . . ?
C1 N1 C6 O2 176.39(14) . . . . ?
C5 N1 C6 O2 -15.7(2) . . . . ?
O1 C6 O2 C7 -7.7(3) . . . . ?
N1 C6 O2 C7 173.03(14) . . . . ?
C6 O2 C7 C10 179.90(16) . . . . ?
C6 O2 C7 C8 62.4(2) . . . . ?
C6 O2 C7 C9 -62.9(2) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
S1 C11 C12 C13 178.81(15) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C12 C11 C16 C15 1.2(3) . . . . ?
S1 C11 C16 C15 -177.06(14) . . . . ?
C14 C15 C16 C11 -1.6(3) . . . . ?
N1 C5 C17 C18 -163.68(15) . . . . ?
C4 C5 C17 C18 -37.9(2) . . . . ?
N1 C5 C17 C22 22.2(2) . . . . ?
C4 C5 C17 C22 148.04(17) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C5 C17 C18 C19 -175.26(16) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C18 C17 C22 C21 0.6(3) . . . . ?
C5 C17 C22 C21 174.88(16) . . . . ?
C16 C11 S1 C1 -114.48(15) . . . . ?
C12 C11 S1 C1 67.25(16) . . . . ?
N1 C1 S1 C11 -144.31(12) . . . . ?
C2 C1 S1 C11 90.09(13) . . . . ?

_refine_diff_density_max    0.427
_refine_diff_density_min   -0.545
_refine_diff_density_rms    0.154



_publ_section_references
;
    Burla, M. C.; Caliandro, R.; Carrozzini, B.; Cascarano, G. L.; Cuocci, C.;
    Giacovazzo, C.; Mallamo, M.; Mazzone, A.; Polidori, G. (2015), Appl. Cryst.
    48, 306-309.

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

    Rigaku (1998). REQAB. 
    Rigaku Corporation, Tokyo, Japan.

    Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
    Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
    Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn.,
    51, 218-224.
;
_chemical_absolute_configuration  ?



data_1f

_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H25 N O2 S'
_chemical_formula_sum             'C17 H25 N O2 S'
_chemical_formula_weight          307.44

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       orthorhombic
_space_group_IT_number            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'

_cell_length_a                    27.491(19)
_cell_length_b                    5.651(4)
_cell_length_c                    21.462(14)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3334(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     100

_cell_measurement_reflns_used     9068

_cell_measurement_theta_min       1.9

_cell_measurement_theta_max       30.7


_exptl_crystal_description        Block

_exptl_crystal_colour             Colorless

_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.225
_exptl_crystal_F_000              1328
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.19

_exptl_crystal_size_mid           0.06

_exptl_crystal_size_min           0.05

_exptl_absorpt_coefficient_mu     0.199
_shelx_estimated_absorpt_T_min    0.963
_shelx_estimated_absorpt_T_max    0.990
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.793
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    ?

_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100

_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Rotating Anode'
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r16
;

_diffrn_measurement_method        'profile data from ω-scans'

_diffrn_detector_area_resol_mean  28.5714

_diffrn_reflns_number             21267
_diffrn_reflns_av_unetI/netI      0.0865
_diffrn_reflns_av_R_equivalents   0.0864
_diffrn_reflns_limit_h_min        -32
_diffrn_reflns_limit_h_max        35
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          1.481
_diffrn_reflns_theta_max          27.498
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.840
_diffrn_reflns_point_group_measured_fraction_full  0.861
_reflns_number_total              6444
_reflns_number_gt                 5684
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.638
_reflns_Friedel_fraction_max      0.672
_reflns_Friedel_fraction_full     0.716

_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r16
;
_computing_structure_solution     'SHELXT-2017/1 (Sheldrick, 2017)'

_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0847P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.31(10)
_chemical_absolute_configuration  unk

_refine_ls_number_reflns          6444
_refine_ls_number_parameters      387
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0817
_refine_ls_R_factor_gt            0.0694
_refine_ls_wR_factor_ref          0.1822
_refine_ls_wR_factor_gt           0.1637
_refine_ls_goodness_of_fit_ref    1.158
_refine_ls_restrained_S_all       1.158
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.49000(16) 0.4067(9) 0.3926(2) 0.0171(10) Uani 1 1 d . . . . .
C1 C 0.47490(19) 0.4256(10) 0.3279(2) 0.0176(11) Uani 1 1 d . . . . .
H1 H 0.492735 0.561338 0.308635 0.021 Uiso 1 1 calc R U . . .
C2 C 0.42054(19) 0.4704(10) 0.3208(3) 0.0231(12) Uani 1 1 d . . . . .
H2 H 0.413471 0.636965 0.331912 0.028 Uiso 1 1 calc R U . . .
H2A H 0.411244 0.447001 0.276703 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3901(2) 0.3093(11) 0.3613(3) 0.0253(13) Uani 1 1 d . . . . .
H3 H 0.394543 0.142831 0.348047 0.030 Uiso 1 1 calc R U . . .
H3A H 0.355300 0.350352 0.356976 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4061(2) 0.3385(12) 0.4296(3) 0.0265(14) Uani 1 1 d . . . . .
H4 H 0.400396 0.503944 0.442822 0.032 Uiso 1 1 calc R U . . .
H4A H 0.386086 0.234169 0.456310 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4601(2) 0.2774(11) 0.4389(3) 0.0221(13) Uani 1 1 d . . . . .
H5 H 0.469535 0.338227 0.480923 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4694(2) 0.0128(11) 0.4392(3) 0.0279(13) Uani 1 1 d . . . . .
H6 H 0.458818 -0.055304 0.399425 0.042 Uiso 1 1 calc R U . . .
H6A H 0.451094 -0.060458 0.473319 0.042 Uiso 1 1 calc R U . . .
H6B H 0.504198 -0.016839 0.445016 0.042 Uiso 1 1 calc R U . . .
C7 C 0.53759(19) 0.4545(9) 0.4094(3) 0.0179(11) Uani 1 1 d . . . . .
O1 O 0.55516(14) 0.3968(7) 0.45920(19) 0.0213(9) Uani 1 1 d . . . . .
O2 O 0.56046(13) 0.5712(7) 0.36349(19) 0.0200(8) Uani 1 1 d . . . . .
C8 C 0.6112(2) 0.6555(10) 0.3710(3) 0.0188(11) Uani 1 1 d . . . . .
C9 C 0.6191(2) 0.7835(11) 0.3099(3) 0.0248(13) Uani 1 1 d . . . . .
H9 H 0.652594 0.843029 0.308069 0.037 Uiso 1 1 calc R U . . .
H9A H 0.596383 0.916502 0.306756 0.037 Uiso 1 1 calc R U . . .
H9B H 0.613578 0.673920 0.275209 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6144(2) 0.8249(10) 0.4262(3) 0.0238(13) Uani 1 1 d . . . . .
H10 H 0.609222 0.736992 0.464988 0.036 Uiso 1 1 calc R U . . .
H10A H 0.589480 0.947700 0.422063 0.036 Uiso 1 1 calc R U . . .
H10B H 0.646686 0.898695 0.426981 0.036 Uiso 1 1 calc R U . . .
C11 C 0.6457(2) 0.4487(11) 0.3781(3) 0.0248(13) Uani 1 1 d . . . . .
H11 H 0.639414 0.368581 0.417781 0.037 Uiso 1 1 calc R U . . .
H11A H 0.679332 0.506242 0.377386 0.037 Uiso 1 1 calc R U . . .
H11B H 0.640737 0.337207 0.343694 0.037 Uiso 1 1 calc R U . . .
S1 S 0.49420(5) 0.1485(2) 0.28757(7) 0.0205(3) Uani 1 1 d . . . . .
C12 C 0.48459(19) 0.2241(10) 0.2081(3) 0.0194(12) Uani 1 1 d . . . . .
C13 C 0.4614(2) 0.0569(10) 0.1701(3) 0.0231(12) Uani 1 1 d . . . . .
H13 H 0.449375 -0.085377 0.187888 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4559(2) 0.0970(12) 0.1068(3) 0.0310(14) Uani 1 1 d . . . . .
H14 H 0.440490 -0.017906 0.081208 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4730(2) 0.3051(11) 0.0810(3) 0.0251(13) Uani 1 1 d . . . . .
H15 H 0.469487 0.333190 0.037564 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4953(2) 0.4730(11) 0.1184(3) 0.0250(13) Uani 1 1 d . . . . .
H16 H 0.506398 0.617456 0.100846 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5014(2) 0.4302(10) 0.1817(3) 0.0209(12) Uani 1 1 d . . . . .
H17 H 0.517363 0.544344 0.206961 0.025 Uiso 1 1 calc R U . . .
N2 N 0.73811(16) 0.4401(9) 0.6050(2) 0.0201(10) Uani 1 1 d . . . . .
C18 C 0.72425(19) 0.4692(10) 0.6691(3) 0.0211(12) Uani 1 1 d . . . . .
H18 H 0.742821 0.606659 0.686328 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6706(2) 0.5189(11) 0.6780(3) 0.0264(13) Uani 1 1 d . . . . .
H19 H 0.663996 0.686068 0.667141 0.032 Uiso 1 1 calc R U . . .
H19A H 0.662148 0.496362 0.722442 0.032 Uiso 1 1 calc R U . . .
C20 C 0.6384(2) 0.3584(13) 0.6381(3) 0.0319(15) Uani 1 1 d . . . . .
H20 H 0.641862 0.192056 0.651840 0.038 Uiso 1 1 calc R U . . .
H20A H 0.603881 0.404969 0.642815 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6536(2) 0.3811(13) 0.5706(3) 0.0346(16) Uani 1 1 d . . . . .
H21 H 0.648849 0.546832 0.556874 0.041 Uiso 1 1 calc R U . . .
H21A H 0.632457 0.279052 0.544590 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7069(2) 0.3105(11) 0.5605(3) 0.0247(13) Uani 1 1 d . . . . .
H22 H 0.716319 0.361966 0.517547 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7146(3) 0.0454(13) 0.5643(3) 0.0356(16) Uani 1 1 d . . . . .
H23 H 0.749371 0.009967 0.560019 0.053 Uiso 1 1 calc R U . . .
H23A H 0.696551 -0.032564 0.530745 0.053 Uiso 1 1 calc R U . . .
H23B H 0.702981 -0.012661 0.604669 0.053 Uiso 1 1 calc R U . . .
C24 C 0.7852(2) 0.4798(10) 0.5861(3) 0.0199(11) Uani 1 1 d . . . . .
O3 O 0.80139(15) 0.4230(7) 0.53616(18) 0.0251(9) Uani 1 1 d . . . . .
O4 O 0.80965(13) 0.5963(7) 0.63082(19) 0.0209(9) Uani 1 1 d . . . . .
C25 C 0.86064(18) 0.6705(9) 0.6231(3) 0.0168(11) Uani 1 1 d . . . . .
C26 C 0.8663(2) 0.8306(10) 0.5670(3) 0.0249(13) Uani 1 1 d . . . . .
H26 H 0.859364 0.740876 0.528922 0.037 Uiso 1 1 calc R U . . .
H26A H 0.899738 0.890922 0.565320 0.037 Uiso 1 1 calc R U . . .
H26B H 0.843608 0.963558 0.570334 0.037 Uiso 1 1 calc R U . . .
C27 C 0.8933(2) 0.4562(10) 0.6190(3) 0.0258(13) Uani 1 1 d . . . . .
H27 H 0.886668 0.350586 0.654173 0.039 Uiso 1 1 calc R U . . .
H27A H 0.927361 0.506609 0.620180 0.039 Uiso 1 1 calc R U . . .
H27B H 0.886946 0.372240 0.579826 0.039 Uiso 1 1 calc R U . . .
C28 C 0.8689(2) 0.8030(12) 0.6836(3) 0.0267(14) Uani 1 1 d . . . . .
H28 H 0.846879 0.939106 0.685609 0.040 Uiso 1 1 calc R U . . .
H28A H 0.902667 0.858223 0.685385 0.040 Uiso 1 1 calc R U . . .
H28B H 0.862515 0.697237 0.718823 0.040 Uiso 1 1 calc R U . . .
S2 S 0.74328(5) 0.1991(2) 0.71278(6) 0.0208(3) Uani 1 1 d . . . . .
C29 C 0.73322(19) 0.2819(10) 0.7914(3) 0.0186(11) Uani 1 1 d . . . . .
C30 C 0.7523(2) 0.4879(11) 0.8178(3) 0.0230(12) Uani 1 1 d . . . . .
H30 H 0.770207 0.595607 0.792651 0.028 Uiso 1 1 calc R U . . .
C31 C 0.7453(2) 0.5355(12) 0.8804(3) 0.0280(14) Uani 1 1 d . . . . .
H31 H 0.757589 0.678219 0.897726 0.034 Uiso 1 1 calc R U . . .
C32 C 0.7208(2) 0.3783(13) 0.9176(3) 0.0307(15) Uani 1 1 d . . . . .
H32 H 0.716183 0.412577 0.960518 0.037 Uiso 1 1 calc R U . . .
C33 C 0.7030(2) 0.1733(13) 0.8932(3) 0.0318(15) Uani 1 1 d . . . . .
H33 H 0.686893 0.063395 0.919625 0.038 Uiso 1 1 calc R U . . .
C34 C 0.7082(2) 0.1224(11) 0.8296(3) 0.0256(13) Uani 1 1 d . . . . .
H34 H 0.694840 -0.018650 0.812632 0.031 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C7 1.384(7) . ?
N1 C1 1.453(7) . ?
N1 C5 1.482(7) . ?
C1 C2 1.523(7) . ?
C1 S1 1.867(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.510(9) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.539(9) . ?
C3 H3 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.536(8) . ?
C4 H4 0.9900 . ?
C4 H4A 0.9900 . ?
C5 C6 1.517(9) . ?
C5 H5 1.0000 . ?
C6 H6 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 O1 1.217(7) . ?
C7 O2 1.342(7) . ?
O2 C8 1.483(6) . ?
C8 C11 1.513(8) . ?
C8 C9 1.514(8) . ?
C8 C10 1.525(8) . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
S1 C12 1.779(7) . ?
C12 C17 1.375(8) . ?
C12 C13 1.401(8) . ?
C13 C14 1.386(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N2 C24 1.374(7) . ?
N2 C18 1.438(8) . ?
N2 C22 1.478(8) . ?
C18 C19 1.513(8) . ?
C18 S2 1.866(6) . ?
C18 H18 1.0000 . ?
C19 C20 1.530(9) . ?
C19 H19 0.9900 . ?
C19 H19A 0.9900 . ?
C20 C21 1.513(10) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.536(9) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.515(10) . ?
C22 H22 1.0000 . ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 O3 1.205(7) . ?
C24 O4 1.344(7) . ?
O4 C25 1.473(6) . ?
C25 C27 1.510(8) . ?
C25 C26 1.514(8) . ?
C25 C28 1.516(8) . ?
C26 H26 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 H27 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 H28 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
S2 C29 1.773(6) . ?
C29 C30 1.397(8) . ?
C29 C34 1.399(8) . ?
C30 C31 1.384(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.372(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.362(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.403(9) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C7 N1 C1 120.3(5) . . ?
C7 N1 C5 116.5(5) . . ?
C1 N1 C5 121.2(4) . . ?
N1 C1 C2 112.8(4) . . ?
N1 C1 S1 107.5(4) . . ?
C2 C1 S1 111.8(4) . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
S1 C1 H1 108.2 . . ?
C3 C2 C1 112.7(5) . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
H2 C2 H2A 107.8 . . ?
C2 C3 C4 109.0(5) . . ?
C2 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
H3 C3 H3A 108.3 . . ?
C5 C4 C3 112.0(5) . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
H4 C4 H4A 107.9 . . ?
N1 C5 C6 113.3(5) . . ?
N1 C5 C4 109.8(5) . . ?
C6 C5 C4 112.6(5) . . ?
N1 C5 H5 106.9 . . ?
C6 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C5 C6 H6 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C7 O2 126.2(5) . . ?
O1 C7 N1 123.5(5) . . ?
O2 C7 N1 110.3(5) . . ?
C7 O2 C8 121.2(4) . . ?
O2 C8 C11 110.6(4) . . ?
O2 C8 C9 101.2(4) . . ?
C11 C8 C9 111.5(5) . . ?
O2 C8 C10 109.9(5) . . ?
C11 C8 C10 111.7(5) . . ?
C9 C8 C10 111.4(5) . . ?
C8 C9 H9 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C10 H10 109.5 . . ?
C8 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C11 H11 109.5 . . ?
C8 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 S1 C1 101.6(3) . . ?
C17 C12 C13 119.0(6) . . ?
C17 C12 S1 123.3(5) . . ?
C13 C12 S1 117.6(5) . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.6(6) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.0(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.1(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.6(6) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C24 N2 C18 120.9(5) . . ?
C24 N2 C22 115.9(5) . . ?
C18 N2 C22 121.5(5) . . ?
N2 C18 C19 113.6(5) . . ?
N2 C18 S2 108.2(4) . . ?
C19 C18 S2 111.2(4) . . ?
N2 C18 H18 107.9 . . ?
C19 C18 H18 107.9 . . ?
S2 C18 H18 107.9 . . ?
C18 C19 C20 112.6(5) . . ?
C18 C19 H19 109.1 . . ?
C20 C19 H19 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
H19 C19 H19A 107.8 . . ?
C21 C20 C19 109.1(5) . . ?
C21 C20 H20 109.9 . . ?
C19 C20 H20 109.9 . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
H20 C20 H20A 108.3 . . ?
C20 C21 C22 112.1(5) . . ?
C20 C21 H21 109.2 . . ?
C22 C21 H21 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
H21 C21 H21A 107.9 . . ?
N2 C22 C23 111.9(5) . . ?
N2 C22 C21 109.5(5) . . ?
C23 C22 C21 112.5(5) . . ?
N2 C22 H22 107.5 . . ?
C23 C22 H22 107.5 . . ?
C21 C22 H22 107.5 . . ?
C22 C23 H23 109.5 . . ?
C22 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C24 O4 125.5(5) . . ?
O3 C24 N2 124.5(5) . . ?
O4 C24 N2 109.9(5) . . ?
C24 O4 C25 122.4(4) . . ?
O4 C25 C27 110.1(4) . . ?
O4 C25 C26 111.0(5) . . ?
C27 C25 C26 111.8(5) . . ?
O4 C25 C28 100.8(4) . . ?
C27 C25 C28 110.9(5) . . ?
C26 C25 C28 111.8(5) . . ?
C25 C26 H26 109.5 . . ?
C25 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C27 H27 109.5 . . ?
C25 C27 H27A 109.5 . . ?
H27 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C28 H28 109.5 . . ?
C25 C28 H28A 109.5 . . ?
H28 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 S2 C18 102.6(3) . . ?
C30 C29 C34 119.0(6) . . ?
C30 C29 S2 123.2(5) . . ?
C34 C29 S2 117.7(5) . . ?
C31 C30 C29 120.2(6) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C32 C31 C30 120.5(6) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C33 C32 C31 120.3(6) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 120.8(6) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C29 C34 C33 119.2(6) . . ?
C29 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C7 N1 C1 C2 -155.7(5) . . . . ?
C5 N1 C1 C2 40.8(7) . . . . ?
C7 N1 C1 S1 80.5(5) . . . . ?
C5 N1 C1 S1 -82.9(5) . . . . ?
N1 C1 C2 C3 -46.6(6) . . . . ?
S1 C1 C2 C3 74.8(6) . . . . ?
C1 C2 C3 C4 56.4(6) . . . . ?
C2 C3 C4 C5 -59.4(7) . . . . ?
C7 N1 C5 C6 -79.9(6) . . . . ?
C1 N1 C5 C6 84.2(6) . . . . ?
C7 N1 C5 C4 153.3(5) . . . . ?
C1 N1 C5 C4 -42.7(7) . . . . ?
C3 C4 C5 N1 50.6(7) . . . . ?
C3 C4 C5 C6 -76.6(7) . . . . ?
C1 N1 C7 O1 -164.4(5) . . . . ?
C5 N1 C7 O1 -0.2(8) . . . . ?
C1 N1 C7 O2 15.7(7) . . . . ?
C5 N1 C7 O2 179.9(5) . . . . ?
O1 C7 O2 C8 -3.3(8) . . . . ?
N1 C7 O2 C8 176.6(4) . . . . ?
C7 O2 C8 C11 64.6(6) . . . . ?
C7 O2 C8 C9 -177.1(5) . . . . ?
C7 O2 C8 C10 -59.2(6) . . . . ?
N1 C1 S1 C12 -168.7(4) . . . . ?
C2 C1 S1 C12 66.9(5) . . . . ?
C1 S1 C12 C17 49.3(5) . . . . ?
C1 S1 C12 C13 -135.0(5) . . . . ?
C17 C12 C13 C14 0.6(9) . . . . ?
S1 C12 C13 C14 -175.3(5) . . . . ?
C12 C13 C14 C15 -0.7(10) . . . . ?
C13 C14 C15 C16 -0.3(10) . . . . ?
C14 C15 C16 C17 1.4(9) . . . . ?
C13 C12 C17 C16 0.4(8) . . . . ?
S1 C12 C17 C16 176.1(4) . . . . ?
C15 C16 C17 C12 -1.4(8) . . . . ?
C24 N2 C18 C19 156.1(5) . . . . ?
C22 N2 C18 C19 -39.8(7) . . . . ?
C24 N2 C18 S2 -79.9(6) . . . . ?
C22 N2 C18 S2 84.2(5) . . . . ?
N2 C18 C19 C20 44.5(7) . . . . ?
S2 C18 C19 C20 -77.9(6) . . . . ?
C18 C19 C20 C21 -55.2(7) . . . . ?
C19 C20 C21 C22 59.6(7) . . . . ?
C24 N2 C22 C23 81.9(6) . . . . ?
C18 N2 C22 C23 -83.0(7) . . . . ?
C24 N2 C22 C21 -152.6(5) . . . . ?
C18 N2 C22 C21 42.5(7) . . . . ?
C20 C21 C22 N2 -51.6(7) . . . . ?
C20 C21 C22 C23 73.6(7) . . . . ?
C18 N2 C24 O3 167.3(5) . . . . ?
C22 N2 C24 O3 2.3(9) . . . . ?
C18 N2 C24 O4 -14.4(7) . . . . ?
C22 N2 C24 O4 -179.4(5) . . . . ?
O3 C24 O4 C25 0.3(9) . . . . ?
N2 C24 O4 C25 -178.0(4) . . . . ?
C24 O4 C25 C27 -66.1(7) . . . . ?
C24 O4 C25 C26 58.2(7) . . . . ?
C24 O4 C25 C28 176.7(5) . . . . ?
N2 C18 S2 C29 170.6(4) . . . . ?
C19 C18 S2 C29 -63.9(5) . . . . ?
C18 S2 C29 C30 -53.0(5) . . . . ?
C18 S2 C29 C34 132.3(5) . . . . ?
C34 C29 C30 C31 -1.8(9) . . . . ?
S2 C29 C30 C31 -176.4(5) . . . . ?
C29 C30 C31 C32 1.9(9) . . . . ?
C30 C31 C32 C33 -0.1(10) . . . . ?
C31 C32 C33 C34 -1.8(11) . . . . ?
C30 C29 C34 C33 -0.1(9) . . . . ?
S2 C29 C34 C33 174.9(5) . . . . ?
C32 C33 C34 C29 1.9(10) . . . . ?

_refine_diff_density_max    0.338
_refine_diff_density_min   -0.423
_refine_diff_density_rms    0.104



_publ_section_references
;
    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

    Rigaku (1998). REQAB. 
    Rigaku Corporation, Tokyo, Japan.

    Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses.
    Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses,
    Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn.,
    51, 218-224.
;
