 
data_190410i
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H25 N3 O3 S' 
_chemical_formula_sum             'C22 H25 N3 O3 S'
_chemical_formula_weight          411.51
 
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'
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    17.4461(15)
_cell_length_b                    6.7560(6)
_cell_length_c                    21.3479(19)
_cell_angle_alpha                 90.00
_cell_angle_beta                  119.320(4)
_cell_angle_gamma                 90.00
_cell_volume                      2193.9(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     298(2)
_cell_measurement_reflns_used     1217 
_cell_measurement_theta_min       2.678 
_cell_measurement_theta_max       20.817 
  
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.27 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.246 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              872 
_exptl_absorpt_coefficient_mu     0.174 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9544 
_exptl_absorpt_correction_T_max   0.9828 
_exptl_absorpt_process_details    sadabs 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       298(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             10595
_diffrn_reflns_av_R_equivalents   0.0716
_diffrn_reflns_av_sigmaI/netI     0.0827
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.19
_diffrn_reflns_theta_max          25.02
_reflns_number_total              3857
_reflns_number_gt                 1991
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL'
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3857
_refine_ls_number_parameters      262
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1088
_refine_ls_R_factor_gt            0.0583
_refine_ls_wR_factor_ref          0.1596
_refine_ls_wR_factor_gt           0.1379
_refine_ls_goodness_of_fit_ref    0.868
_refine_ls_restrained_S_all       0.868
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.3085(2) 0.0821(5) 0.46422(16) 0.0465(8) Uani 1 1 d . . .
C2 C 0.22352(19) 0.1259(5) 0.44726(16) 0.0446(8) Uani 1 1 d . . .
C3 C 0.20675(19) 0.0224(5) 0.49864(16) 0.0474(8) Uani 1 1 d . . .
C4 C 0.2840(2) -0.0792(5) 0.54528(17) 0.0536(9) Uani 1 1 d . . .
C5 C 0.16844(19) 0.2760(5) 0.39199(17) 0.0461(8) Uani 1 1 d . . .
C6 C 0.1448(2) 0.2513(5) 0.32037(18) 0.0555(9) Uani 1 1 d . . .
H6 H 0.1586 0.1334 0.3056 0.067 Uiso 1 1 calc R . .
C7 C 0.1010(2) 0.3990(6) 0.27009(19) 0.0679(11) Uani 1 1 d . . .
H7 H 0.0861 0.3794 0.2223 0.081 Uiso 1 1 calc R . .
C8 C 0.0794(2) 0.5737(6) 0.2905(2) 0.0760(12) Uani 1 1 d . . .
H8 H 0.0507 0.6737 0.2571 0.091 Uiso 1 1 calc R . .
C9 C 0.1008(3) 0.5984(6) 0.3611(3) 0.0841(13) Uani 1 1 d . . .
H9 H 0.0856 0.7153 0.3753 0.101 Uiso 1 1 calc R . .
C10 C 0.1445(2) 0.4520(6) 0.4112(2) 0.0687(11) Uani 1 1 d . . .
H10 H 0.1581 0.4717 0.4587 0.082 Uiso 1 1 calc R . .
C11 C 0.1240(2) 0.0083(5) 0.50156(18) 0.0487(8) Uani 1 1 d . . .
C12 C 0.3084(2) -0.2129(6) 0.6097(2) 0.0730(12) Uani 1 1 d . . .
H12 H 0.2552 -0.2386 0.6130 0.088 Uiso 1 1 calc R . .
C13 C 0.3466(3) -0.4112(6) 0.6042(2) 0.0918(14) Uani 1 1 d . . .
H13A H 0.3039 -0.4811 0.5624 0.138 Uiso 1 1 calc R . .
H13B H 0.3616 -0.4885 0.6463 0.138 Uiso 1 1 calc R . .
H13C H 0.3984 -0.3887 0.6002 0.138 Uiso 1 1 calc R . .
C14 C 0.3755(3) -0.1050(7) 0.6790(2) 0.1061(17) Uani 1 1 d . . .
H14A H 0.4265 -0.0705 0.6753 0.159 Uiso 1 1 calc R . .
H14B H 0.3924 -0.1906 0.7196 0.159 Uiso 1 1 calc R . .
H14C H 0.3492 0.0130 0.6851 0.159 Uiso 1 1 calc R . .
C15 C 0.3781(2) 0.3757(6) 0.4419(2) 0.0732(11) Uani 1 1 d . . .
H15A H 0.3252 0.4402 0.4071 0.110 Uiso 1 1 calc R . .
H15B H 0.4247 0.4037 0.4316 0.110 Uiso 1 1 calc R . .
H15C H 0.3939 0.4235 0.4891 0.110 Uiso 1 1 calc R . .
C16 C 0.30985(19) 0.0162(5) 0.30337(16) 0.0475(8) Uani 1 1 d . . .
C17 C 0.2967(2) 0.1816(5) 0.25986(18) 0.0595(10) Uani 1 1 d . . .
H17 H 0.3353 0.2882 0.2772 0.071 Uiso 1 1 calc R . .
C18 C 0.2257(2) 0.1858(5) 0.19063(18) 0.0618(10) Uani 1 1 d . . .
H18 H 0.2167 0.2967 0.1621 0.074 Uiso 1 1 calc R . .
C19 C 0.1678(2) 0.0271(5) 0.16324(17) 0.0533(9) Uani 1 1 d . . .
C20 C 0.1837(2) -0.1366(5) 0.20639(19) 0.0612(10) Uani 1 1 d . . .
H20 H 0.1466 -0.2455 0.1883 0.073 Uiso 1 1 calc R . .
C21 C 0.2538(2) -0.1437(5) 0.27640(19) 0.0571(9) Uani 1 1 d . . .
H21 H 0.2628 -0.2553 0.3047 0.069 Uiso 1 1 calc R . .
C22 C 0.0897(2) 0.0351(6) 0.08747(18) 0.0698(11) Uani 1 1 d . . .
H22A H 0.0937 0.1518 0.0636 0.105 Uiso 1 1 calc R . .
H22B H 0.0361 0.0384 0.0898 0.105 Uiso 1 1 calc R . .
H22C H 0.0901 -0.0800 0.0612 0.105 Uiso 1 1 calc R . .
N1 N 0.34405(16) -0.0405(4) 0.52350(14) 0.0552(8) Uani 1 1 d . . .
H1 H 0.3968 -0.0862 0.5439 0.066 Uiso 1 1 calc R . .
N2 N 0.36336(16) 0.1603(4) 0.43881(13) 0.0503(7) Uani 1 1 d . . .
N3 N 0.04910(16) 0.0617(4) 0.44125(14) 0.0609(8) Uani 1 1 d . . .
H3A H -0.0008 0.0532 0.4400 0.073 Uiso 1 1 calc R . .
H3B H 0.0516 0.1041 0.4043 0.073 Uiso 1 1 calc R . .
O1 O 0.12034(14) -0.0526(4) 0.55465(12) 0.0635(7) Uani 1 1 d . . .
O2 O 0.40574(14) -0.1771(3) 0.42108(12) 0.0649(7) Uani 1 1 d U . .
O3 O 0.46828(13) 0.1199(4) 0.39371(11) 0.0639(7) Uani 1 1 d . . .
S1 S 0.39542(5) 0.01930(13) 0.39297(4) 0.0510(3) Uani 1 1 d 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
C1 C2 1.375(4) . ?
C1 N1 1.380(4) . ?
C1 N2 1.413(4) . ?
C2 C3 1.446(4) . ?
C2 C5 1.494(4) . ?
C3 C4 1.402(4) . ?
C3 C11 1.479(4) . ?
C4 N1 1.363(4) . ?
C4 C12 1.522(4) . ?
C5 C6 1.385(4) . ?
C5 C10 1.388(4) . ?
C6 C7 1.389(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.236(4) . ?
C11 N3 1.359(4) . ?
C12 C13 1.527(5) . ?
C12 C14 1.547(5) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N2 1.474(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.379(4) . ?
C16 C17 1.398(4) . ?
C16 S1 1.758(3) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C19 C22 1.522(4) . ?
C20 C21 1.394(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 H1 0.8600 . ?
N2 S1 1.648(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O2 S1 1.431(2) . ?
O3 S1 1.435(2) . ?
 
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
C2 C1 N1 108.2(3) . . ?
C2 C1 N2 131.6(3) . . ?
N1 C1 N2 119.5(3) . . ?
C1 C2 C3 106.8(3) . . ?
C1 C2 C5 123.2(3) . . ?
C3 C2 C5 129.5(3) . . ?
C4 C3 C2 107.1(3) . . ?
C4 C3 C11 123.9(3) . . ?
C2 C3 C11 128.9(3) . . ?
N1 C4 C3 107.2(3) . . ?
N1 C4 C12 120.1(3) . . ?
C3 C4 C12 132.7(3) . . ?
C6 C5 C10 117.3(3) . . ?
C6 C5 C2 121.3(3) . . ?
C10 C5 C2 121.2(3) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 118.9(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
O1 C11 N3 120.0(3) . . ?
O1 C11 C3 123.4(3) . . ?
N3 C11 C3 116.6(3) . . ?
C4 C12 C13 113.0(3) . . ?
C4 C12 C14 109.3(3) . . ?
C13 C12 C14 109.5(3) . . ?
C4 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C14 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 119.8(3) . . ?
C21 C16 S1 120.9(3) . . ?
C17 C16 S1 119.3(3) . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 118.1(3) . . ?
C20 C19 C22 121.4(3) . . ?
C18 C19 C22 120.5(3) . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C16 C21 C20 119.4(3) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 N1 C1 110.7(2) . . ?
C4 N1 H1 124.7 . . ?
C1 N1 H1 124.7 . . ?
C1 N2 C15 119.2(3) . . ?
C1 N2 S1 120.2(2) . . ?
C15 N2 S1 119.7(2) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
O2 S1 O3 120.38(14) . . ?
O2 S1 N2 107.27(14) . . ?
O3 S1 N2 106.04(15) . . ?
O2 S1 C16 108.09(15) . . ?
O3 S1 C16 107.06(14) . . ?
N2 S1 C16 107.39(14) . . ?
 
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
N1 C1 C2 C3 -0.6(4) . . . . ?
N2 C1 C2 C3 -170.7(3) . . . . ?
N1 C1 C2 C5 171.8(3) . . . . ?
N2 C1 C2 C5 1.7(5) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C5 C2 C3 C4 -171.2(3) . . . . ?
C1 C2 C3 C11 -175.5(3) . . . . ?
C5 C2 C3 C11 12.8(6) . . . . ?
C2 C3 C4 N1 -0.2(4) . . . . ?
C11 C3 C4 N1 176.0(3) . . . . ?
C2 C3 C4 C12 -180.0(4) . . . . ?
C11 C3 C4 C12 -3.8(6) . . . . ?
C1 C2 C5 C6 63.5(4) . . . . ?
C3 C2 C5 C6 -126.0(4) . . . . ?
C1 C2 C5 C10 -111.7(4) . . . . ?
C3 C2 C5 C10 58.8(5) . . . . ?
C10 C5 C6 C7 1.7(5) . . . . ?
C2 C5 C6 C7 -173.7(3) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C5 0.3(6) . . . . ?
C6 C5 C10 C9 -1.6(5) . . . . ?
C2 C5 C10 C9 173.8(3) . . . . ?
C4 C3 C11 O1 18.5(5) . . . . ?
C2 C3 C11 O1 -166.1(3) . . . . ?
C4 C3 C11 N3 -159.9(3) . . . . ?
C2 C3 C11 N3 15.5(5) . . . . ?
N1 C4 C12 C13 -52.0(5) . . . . ?
C3 C4 C12 C13 127.8(4) . . . . ?
N1 C4 C12 C14 70.1(4) . . . . ?
C3 C4 C12 C14 -110.1(4) . . . . ?
C21 C16 C17 C18 2.0(5) . . . . ?
S1 C16 C17 C18 -175.6(3) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C17 C18 C19 C22 179.4(3) . . . . ?
C18 C19 C20 C21 2.0(5) . . . . ?
C22 C19 C20 C21 -178.5(3) . . . . ?
C17 C16 C21 C20 -1.2(5) . . . . ?
S1 C16 C21 C20 176.4(3) . . . . ?
C19 C20 C21 C16 -0.8(5) . . . . ?
C3 C4 N1 C1 -0.2(4) . . . . ?
C12 C4 N1 C1 179.6(3) . . . . ?
C2 C1 N1 C4 0.5(4) . . . . ?
N2 C1 N1 C4 172.0(3) . . . . ?
C2 C1 N2 C15 54.1(5) . . . . ?
N1 C1 N2 C15 -115.0(3) . . . . ?
C2 C1 N2 S1 -114.7(4) . . . . ?
N1 C1 N2 S1 76.1(3) . . . . ?
C1 N2 S1 O2 -33.7(3) . . . . ?
C15 N2 S1 O2 157.5(2) . . . . ?
C1 N2 S1 O3 -163.5(2) . . . . ?
C15 N2 S1 O3 27.7(3) . . . . ?
C1 N2 S1 C16 82.3(3) . . . . ?
C15 N2 S1 C16 -86.5(3) . . . . ?
C21 C16 S1 O2 13.4(3) . . . . ?
C17 C16 S1 O2 -168.9(2) . . . . ?
C21 C16 S1 O3 144.5(3) . . . . ?
C17 C16 S1 O3 -37.9(3) . . . . ?
C21 C16 S1 N2 -102.0(3) . . . . ?
C17 C16 S1 N2 75.6(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.408
_refine_diff_density_min   -0.361
_refine_diff_density_rms    0.051
