 
data_shelx
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety  'C22 H25 N O' 
_chemical_formula_sum 'C22 H25 N O' 
_chemical_formula_weight          319.43

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_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+1/2, -z'
 
_cell_length_a                    10.2688(12)
_cell_length_b                    9.2623(10)
_cell_length_c                    11.0055(13)
_cell_angle_alpha                 90
_cell_angle_beta                  115.655(4)
_cell_angle_gamma                 90
_cell_volume                      943.57(19)
_cell_formula_units_Z             2
_cell_measurement_temperature     296
_cell_measurement_reflns_used      4298
_cell_measurement_theta_min        2.27
_cell_measurement_theta_max       25.89
 
_exptl_crystal_description       'block'
_exptl_crystal_colour            'colourless'
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.124          
_exptl_crystal_F_000              344
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_absorpt_coefficient_mu     0.068
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    'none' 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       296
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?                       
_diffrn_measurement_device_type  'Bruker APEX-3 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number             22679
_diffrn_reflns_av_unetI/netI      0.0733
_diffrn_reflns_av_R_equivalents   0.0795
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.009
_diffrn_reflns_theta_max          25.994
_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   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3700
_reflns_number_gt                 2029
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.880
_reflns_Friedel_fraction_max      1.000
_reflns_Friedel_fraction_full     1.000
 
_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      'APEX3 (Bruker, 2013)'
_computing_cell_refinement      'SAINT(Bruker, 2013)'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution     'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement    'SHELXL-2013 (Sheldrick, 2015)'
_computing_molecular_graphics     'Mercury (Macrae, 2008)'
_computing_publication_material   'WinGX (Farrugia, 2012)'
 
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0292P)²+1.3699P] 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
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration  'syn'
_refine_ls_number_reflns          3700
_refine_ls_number_parameters      209
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1644
_refine_ls_R_factor_gt            0.0873
_refine_ls_wR_factor_ref          0.1809
_refine_ls_wR_factor_gt           0.1495
_refine_ls_goodness_of_fit_ref    0.948
_refine_ls_restrained_S_all       0.948
_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
C1 C 0.0916(9) 0.8006(13) 0.2131(10) 0.093(3) Uani 1 1 d . . . . .
H1 H 0.0434 0.8776 0.2297 0.112 Uiso 1 1 calc R U . . .
C2 C 0.0363(11) 0.7381(15) 0.0846(10) 0.113(4) Uani 1 1 d . . . . .
H2 H -0.0494 0.7724 0.0165 0.136 Uiso 1 1 calc R U . . .
C3 C 0.1074(12) 0.6278(14) 0.0594(10) 0.098(3) Uani 1 1 d . . . . .
H3 H 0.0740 0.5895 -0.0270 0.117 Uiso 1 1 calc R U . . .
C4 C 0.2272(10) 0.5737(13) 0.1607(10) 0.083(3) Uani 1 1 d . . . . .
H4 H 0.2739 0.4952 0.1445 0.099 Uiso 1 1 calc R U . . .
C5 C 0.2813(8) 0.6330(12) 0.2875(8) 0.066(2) Uani 1 1 d . . . . .
H5 H 0.3635 0.5933 0.3561 0.079 Uiso 1 1 calc R U . . .
C6 C 0.2166(7) 0.7487(11) 0.3146(7) 0.0536(18) Uani 1 1 d . . . . .
C7 C 0.2791(7) 0.8224(11) 0.4500(7) 0.0566(18) Uani 1 1 d . . . . .
H7A H 0.3415 0.9002 0.4482 0.068 Uiso 1 1 calc R U . . .
H7B H 0.2008 0.8652 0.4645 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5062(7) 0.7273(12) 0.6234(7) 0.0541(18) Uani 1 1 d . . . . .
C9 C 0.5521(8) 0.6154(11) 0.7278(7) 0.0593(19) Uani 1 1 d . . . . .
C10 C 0.6888(10) 0.5889(14) 0.8042(8) 0.096(3) Uani 1 1 d . . . . .
H10A H 0.7598 0.6418 0.7929 0.115 Uiso 1 1 calc R U . . .
H10B H 0.7149 0.5173 0.8697 0.115 Uiso 1 1 calc R U . . .
C11 C 0.4233(9) 0.5536(11) 0.7361(9) 0.078(2) Uani 1 1 d . . . . .
H11 H 0.4194 0.5915 0.8176 0.094 Uiso 1 1 calc R U . . .
C12 C 0.2916(7) 0.6190(11) 0.6098(7) 0.0565(19) Uani 1 1 d . . . . .
H12 H 0.2508 0.5441 0.5406 0.068 Uiso 1 1 calc R U . . .
C13 C 0.1740(7) 0.6806(11) 0.6399(7) 0.0485(17) Uani 1 1 d . . . . .
C14 C 0.0336(8) 0.6353(12) 0.5737(8) 0.071(2) Uani 1 1 d . . . . .
H14 H 0.0111 0.5625 0.5096 0.086 Uiso 1 1 calc R U . . .
C15 C -0.0736(9) 0.6932(13) 0.5988(10) 0.084(3) Uani 1 1 d . . . . .
H15 H -0.1674 0.6588 0.5523 0.101 Uiso 1 1 calc R U . . .
C16 C -0.0462(10) 0.8016(13) 0.6914(10) 0.085(3) Uani 1 1 d . . . . .
H16 H -0.1203 0.8408 0.7080 0.102 Uiso 1 1 calc R U . . .
C17 C 0.0918(10) 0.8508(12) 0.7589(9) 0.085(3) Uani 1 1 d . . . . .
H17 H 0.1122 0.9252 0.8211 0.102 Uiso 1 1 calc R U . . .
C18 C 0.2034(8) 0.7896(12) 0.7347(8) 0.069(2) Uani 1 1 d . . . . .
H18 H 0.2977 0.8222 0.7826 0.083 Uiso 1 1 calc R U . . .
C20 C 0.3321 0.3173 0.7880 0.1307(18) Uani 1 1 d . . . . .
H20 H 0.2336 0.3385 0.7208 0.157 Uiso 1 1 calc R U . . .
C21 C 0.3402(17) 0.359(2) 0.9238(12) 0.187(7) Uani 1 1 d . . . . .
H21A H 0.3140 0.4589 0.9221 0.281 Uiso 1 1 calc R U . . .
H21B H 0.4369 0.3450 0.9919 0.281 Uiso 1 1 calc R U . . .
H21C H 0.2749 0.3003 0.9435 0.281 Uiso 1 1 calc R U . . .
C22 C 0.3573(16) 0.1554(13) 0.7776(16) 0.174(6) Uani 1 1 d . . . . .
H22A H 0.4508 0.1290 0.8460 0.261 Uiso 1 1 calc R U . . .
H22B H 0.3526 0.1346 0.6903 0.261 Uiso 1 1 calc R U . . .
H22C H 0.2843 0.1012 0.7899 0.261 Uiso 1 1 calc R U . . .
N1 N 0.3610(5) 0.7287(10) 0.5628(5) 0.0496(14) Uani 1 1 d . . . . .
O1 O 0.5841(5) 0.8064(10) 0.5929(5) 0.0781(17) Uani 1 1 d . . . . .
C19 C 0.4311 0.3957 0.7463 0.0993(15) Uani 1 1 d . . . . .
H19A H 0.5289 0.3705 0.8093 0.119 Uiso 1 1 calc R U . . .
H19B H 0.4163 0.3583 0.6590 0.119 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
C1 C6 1.372(10) . ?
C1 C2 1.401(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(9) . ?
C7 N1 1.448(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.234(8) . ?
C8 N1 1.344(8) . ?
C8 C9 1.465(10) . ?
C9 C10 1.310(10) . ?
C9 C11 1.480(10) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C19 1.467(10) . ?
C11 C12 1.581(10) . ?
C11 H11 0.9800 . ?
C12 N1 1.459(8) . ?
C12 C13 1.496(9) . ?
C12 H12 0.9800 . ?
C13 C14 1.370(9) . ?
C13 C18 1.388(9) . ?
C14 C15 1.357(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C19 1.4749(2) . ?
C20 C21 1.510(11) . ?
C20 C22 1.534(12) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
 
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 C1 C2 120.3(9) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.0(10) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.4(10) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.9(9) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.1(8) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.1(8) . . ?
C5 C6 C7 122.3(6) . . ?
C1 C6 C7 119.6(7) . . ?
N1 C7 C6 114.7(6) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 124.7(7) . . ?
O1 C8 C9 127.4(6) . . ?
N1 C8 C9 107.9(6) . . ?
C10 C9 C8 121.8(8) . . ?
C10 C9 C11 128.8(8) . . ?
C8 C9 C11 109.2(6) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C19 C11 C9 111.7(6) . . ?
C19 C11 C12 116.5(7) . . ?
C9 C11 C12 104.2(6) . . ?
C19 C11 H11 108.0 . . ?
C9 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
N1 C12 C13 112.2(5) . . ?
N1 C12 C11 102.4(5) . . ?
C13 C12 C11 114.6(6) . . ?
N1 C12 H12 109.1 . . ?
C13 C12 H12 109.1 . . ?
C11 C12 H12 109.1 . . ?
C14 C13 C18 117.3(7) . . ?
C14 C13 C12 122.0(7) . . ?
C18 C13 C12 120.7(6) . . ?
C15 C14 C13 122.0(8) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 121.2(8) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.7(8) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 120.2(8) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.5(7) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C20 C21 115.5(6) . . ?
C19 C20 C22 107.3(6) . . ?
C21 C20 C22 112.7(9) . . ?
C19 C20 H20 107.0 . . ?
C21 C20 H20 107.0 . . ?
C22 C20 H20 107.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C7 122.6(5) . . ?
C8 N1 C12 115.1(6) . . ?
C7 N1 C12 122.0(5) . . ?
C11 C19 C20 119.5(3) . . ?
C11 C19 H19A 107.4 . . ?
C20 C19 H19A 107.4 . . ?
C11 C19 H19B 107.4 . . ?
C20 C19 H19B 107.4 . . ?
H19A C19 H19B 107.0 . . ?
 
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 C1 C2 C3 -1.2(16) . . . . ?
C1 C2 C3 C4 3.6(17) . . . . ?
C2 C3 C4 C5 -2.8(15) . . . . ?
C3 C4 C5 C6 -0.6(13) . . . . ?
C4 C5 C6 C1 3.0(11) . . . . ?
C4 C5 C6 C7 -175.7(7) . . . . ?
C2 C1 C6 C5 -2.1(13) . . . . ?
C2 C1 C6 C7 176.6(8) . . . . ?
C5 C6 C7 N1 -30.1(9) . . . . ?
C1 C6 C7 N1 151.2(7) . . . . ?
O1 C8 C9 C10 0.9(12) . . . . ?
N1 C8 C9 C10 -179.9(7) . . . . ?
O1 C8 C9 C11 176.3(8) . . . . ?
N1 C8 C9 C11 -4.6(8) . . . . ?
C10 C9 C11 C19 -49.0(12) . . . . ?
C8 C9 C11 C19 136.1(6) . . . . ?
C10 C9 C11 C12 -175.6(8) . . . . ?
C8 C9 C11 C12 9.4(8) . . . . ?
C19 C11 C12 N1 -134.0(6) . . . . ?
C9 C11 C12 N1 -10.5(7) . . . . ?
C19 C11 C12 C13 104.2(7) . . . . ?
C9 C11 C12 C13 -132.2(6) . . . . ?
N1 C12 C13 C14 119.7(7) . . . . ?
C11 C12 C13 C14 -124.1(7) . . . . ?
N1 C12 C13 C18 -58.8(9) . . . . ?
C11 C12 C13 C18 57.5(8) . . . . ?
C18 C13 C14 C15 -0.1(11) . . . . ?
C12 C13 C14 C15 -178.6(8) . . . . ?
C13 C14 C15 C16 0.6(13) . . . . ?
C14 C15 C16 C17 -0.1(13) . . . . ?
C15 C16 C17 C18 -0.9(13) . . . . ?
C14 C13 C18 C17 -0.9(11) . . . . ?
C12 C13 C18 C17 177.6(7) . . . . ?
C16 C17 C18 C13 1.5(12) . . . . ?
O1 C8 N1 C7 2.1(11) . . . . ?
C9 C8 N1 C7 -177.1(6) . . . . ?
O1 C8 N1 C12 176.2(7) . . . . ?
C9 C8 N1 C12 -3.0(8) . . . . ?
C6 C7 N1 C8 102.6(7) . . . . ?
C6 C7 N1 C12 -71.1(8) . . . . ?
C13 C12 N1 C8 132.1(6) . . . . ?
C11 C12 N1 C8 8.7(8) . . . . ?
C13 C12 N1 C7 -53.8(9) . . . . ?
C11 C12 N1 C7 -177.2(6) . . . . ?
C9 C11 C19 C20 165.4(4) . . . . ?
C12 C11 C19 C20 -75.1(6) . . . . ?
C21 C20 C19 C11 -58.1(9) . . . . ?
C22 C20 C19 C11 175.3(7) . . . . ?
 
_refine_diff_density_max    0.393
_refine_diff_density_min   -0.215
_refine_diff_density_rms    0.038

_shelxl_version_number 2013-4



