# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_dm16776_0m
_database_code_depnum_ccdc_archive 'CCDC 1992436'
loop_
_audit_author_name
_audit_author_address
'Changhua Ding'
;Shanghai University
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Br N O'
_chemical_formula_sum            'C22 H24 Br N O'
_chemical_formula_weight         398.33
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   12.716(2)
_cell_length_b                   12.716(2)
_cell_length_c                   22.693(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3177.7(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    4606
_cell_measurement_temperature    130
_cell_measurement_theta_max      23.936
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.949
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.5685.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28556
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.822
_diffrn_reflns_theta_min         1.849
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3893
_reflns_number_total             5400
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+2.1858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19),
 C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br -0.13248(7) -0.32133(5) 0.57321(4) 0.0595(3) Uani 1 1 d . . . . .
O1 O 0.1147(3) 0.2902(3) 0.61607(17) 0.0278(8) Uani 1 1 d . . . . .
N1 N -0.0279(3) 0.2616(3) 0.54680(18) 0.0191(8) Uani 1 1 d . . . . .
H1 H -0.078552 0.209621 0.520799 0.023 Uiso 1 1 calc R . . . .
C1 C 0.1159(4) 0.4796(4) 0.5274(2) 0.0220(10) Uani 1 1 d . . . . .
H1A H 0.172599 0.482170 0.558659 0.026 Uiso 1 1 calc R . . . .
C2 C 0.1358(5) 0.6078(5) 0.5229(3) 0.0307(12) Uani 1 1 d . . . . .
H2 H 0.084689 0.620610 0.496893 0.037 Uiso 1 1 calc R . . . .
C3 C 0.2170(6) 0.7002(5) 0.5517(3) 0.0398(15) Uani 1 1 d . . . . .
H3A H 0.269809 0.690862 0.578063 0.048 Uiso 1 1 calc R . . . .
H3B H 0.224094 0.777621 0.546556 0.048 Uiso 1 1 calc R . . . .
C4 C 0.1554(5) 0.4463(4) 0.4700(2) 0.0269(11) Uani 1 1 d . . . . .
C5 C 0.2331(5) 0.3999(5) 0.4720(2) 0.0309(12) Uani 1 1 d . . . . .
H5 H 0.257596 0.384595 0.509061 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2758(5) 0.3753(5) 0.4203(3) 0.0425(15) Uani 1 1 d . . . . .
H6 H 0.328621 0.342746 0.422485 0.051 Uiso 1 1 calc R . . . .
C7 C 0.2423(6) 0.3977(6) 0.3657(3) 0.0453(17) Uani 1 1 d . . . . .
H7 H 0.271912 0.380736 0.330669 0.054 Uiso 1 1 calc R . . . .
C8 C 0.1655(6) 0.4448(7) 0.3628(3) 0.0482(18) Uani 1 1 d . . . . .
H8 H 0.142801 0.461547 0.325566 0.058 Uiso 1 1 calc R . . . .
C9 C 0.1214(5) 0.4677(5) 0.4144(3) 0.0369(13) Uani 1 1 d . . . . .
H9 H 0.067126 0.498411 0.411940 0.044 Uiso 1 1 calc R . . . .
C10 C -0.0146(4) 0.3847(4) 0.5482(2) 0.0208(10) Uani 1 1 d . . . . .
C11 C -0.1163(4) 0.3764(5) 0.5077(2) 0.0244(10) Uani 1 1 d . . . . .
H11A H -0.106149 0.458371 0.503110 0.029 Uiso 1 1 calc R . . . .
H11B H -0.107962 0.348169 0.468204 0.029 Uiso 1 1 calc R . . . .
C12 C -0.2434(5) 0.2903(5) 0.5314(3) 0.0302(12) Uani 1 1 d . . . . .
H12A H -0.258251 0.206045 0.530402 0.036 Uiso 1 1 calc R . . . .
H12B H -0.304185 0.294069 0.505669 0.036 Uiso 1 1 calc R . . . .
C13 C -0.2595(5) 0.3219(5) 0.5945(2) 0.0327(13) Uani 1 1 d . . . . .
H13A H -0.340035 0.259699 0.609461 0.039 Uiso 1 1 calc R . . . .
H13B H -0.256530 0.401221 0.594749 0.039 Uiso 1 1 calc R . . . .
C14 C -0.1604(5) 0.3283(5) 0.6349(2) 0.0324(12) Uani 1 1 d . . . . .
H14A H -0.169076 0.355171 0.674668 0.039 Uiso 1 1 calc R . . . .
H14B H -0.169645 0.246487 0.638637 0.039 Uiso 1 1 calc R . . . .
C15 C -0.0355(5) 0.4160(5) 0.6106(2) 0.0257(11) Uani 1 1 d . . . . .
H15A H 0.026637 0.416623 0.637116 0.031 Uiso 1 1 calc R . . . .
H15B H -0.024422 0.498782 0.610496 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0313(4) 0.2235(4) 0.5821(2) 0.0222(10) Uani 1 1 d . . . . .
C17 C -0.0102(4) 0.0904(4) 0.5783(2) 0.0215(9) Uani 1 1 d . . . . .
C18 C -0.1323(5) 0.0042(4) 0.5700(3) 0.0278(11) Uani 1 1 d . . . . .
H18 H -0.190366 0.029822 0.565459 0.033 Uiso 1 1 calc R . . . .
C19 C -0.1697(5) -0.1192(4) 0.5682(3) 0.0331(12) Uani 1 1 d . . . . .
H19 H -0.252815 -0.178313 0.562834 0.040 Uiso 1 1 calc R . . . .
C20 C -0.0828(5) -0.1534(4) 0.5745(3) 0.0327(12) Uani 1 1 d . . . . .
C21 C 0.0385(6) -0.0693(5) 0.5829(3) 0.0412(14) Uani 1 1 d . . . . .
H21 H 0.096669 -0.094937 0.586886 0.049 Uiso 1 1 calc R . . . .
C22 C 0.0744(5) 0.0541(5) 0.5855(2) 0.0298(12) Uani 1 1 d . . . . .
H22 H 0.157203 0.112825 0.592108 0.036 Uiso 1 1 calc R . . . .


_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
Br1 C20 1.900(5) . ?
O1 C16 1.240(6) . ?
N1 H1 0.8800 . ?
N1 C10 1.488(6) . ?
N1 C16 1.345(6) . ?
C1 H1A 1.0000 . ?
C1 C2 1.523(7) . ?
C1 C4 1.531(7) . ?
C1 C10 1.559(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.289(8) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C4 C5 1.381(8) . ?
C4 C9 1.404(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.546(7) . ?
C10 C15 1.530(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.528(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.528(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.503(6) . ?
C17 C18 1.394(7) . ?
C17 C22 1.376(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(8) . ?
C20 C21 1.381(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.399(7) . ?
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
C10 N1 H1 117.4 . . ?
C16 N1 H1 117.4 . . ?
C16 N1 C10 125.2(4) . . ?
C2 C1 H1A 106.4 . . ?
C2 C1 C4 109.7(4) . . ?
C2 C1 C10 113.1(4) . . ?
C4 C1 H1A 106.4 . . ?
C4 C1 C10 114.4(4) . . ?
C10 C1 H1A 106.4 . . ?
C1 C2 H2 117.6 . . ?
C3 C2 C1 124.7(6) . . ?
C3 C2 H2 117.6 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C5 C4 C1 119.6(5) . . ?
C5 C4 C9 117.9(5) . . ?
C9 C4 C1 122.4(5) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(6) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.4(6) . . ?
C8 C9 H9 119.3 . . ?
N1 C10 C1 109.0(4) . . ?
N1 C10 C11 105.3(4) . . ?
N1 C10 C15 110.5(4) . . ?
C11 C10 C1 113.8(4) . . ?
C15 C10 C1 109.6(4) . . ?
C15 C10 C11 108.7(4) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.8(4) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C11 C12 C13 112.0(4) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.1(4) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C13 110.7(5) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C10 C15 H15A 108.8 . . ?
C10 C15 H15B 108.8 . . ?
C14 C15 C10 113.6(4) . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O1 C16 N1 124.4(4) . . ?
O1 C16 C17 120.3(4) . . ?
N1 C16 C17 115.3(4) . . ?
C18 C17 C16 121.3(4) . . ?
C22 C17 C16 118.5(4) . . ?
C22 C17 C18 120.2(4) . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.3(5) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 Br1 118.9(4) . . ?
C21 C20 Br1 119.2(4) . . ?
C21 C20 C19 122.0(5) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.1(5) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 120.0(5) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?

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
Br1 C20 C21 C22 -178.3(5) . . . . ?
O1 C16 C17 C18 143.7(5) . . . . ?
O1 C16 C17 C22 -33.9(7) . . . . ?
N1 C10 C11 C12 65.2(5) . . . . ?
N1 C10 C15 C14 -59.8(5) . . . . ?
N1 C16 C17 C18 -36.3(7) . . . . ?
N1 C16 C17 C22 146.1(5) . . . . ?
C1 C4 C5 C6 -176.3(5) . . . . ?
C1 C4 C9 C8 175.3(5) . . . . ?
C1 C10 C11 C12 -175.5(4) . . . . ?
C1 C10 C15 C14 -179.8(4) . . . . ?
C2 C1 C4 C5 129.5(5) . . . . ?
C2 C1 C4 C9 -46.6(6) . . . . ?
C2 C1 C10 N1 175.7(4) . . . . ?
C2 C1 C10 C11 58.6(5) . . . . ?
C2 C1 C10 C15 -63.3(5) . . . . ?
C4 C1 C2 C3 -110.3(6) . . . . ?
C4 C1 C10 N1 49.2(5) . . . . ?
C4 C1 C10 C11 -67.9(5) . . . . ?
C4 C1 C10 C15 170.2(4) . . . . ?
C4 C5 C6 C7 0.5(9) . . . . ?
C5 C4 C9 C8 -0.9(8) . . . . ?
C5 C6 C7 C8 -0.1(9) . . . . ?
C6 C7 C8 C9 -0.9(10) . . . . ?
C7 C8 C9 C4 1.4(9) . . . . ?
C9 C4 C5 C6 0.0(8) . . . . ?
C10 N1 C16 O1 -8.3(8) . . . . ?
C10 N1 C16 C17 171.7(4) . . . . ?
C10 C1 C2 C3 120.7(6) . . . . ?
C10 C1 C4 C5 -102.2(5) . . . . ?
C10 C1 C4 C9 81.7(6) . . . . ?
C10 C11 C12 C13 54.0(5) . . . . ?
C11 C10 C15 C14 55.3(5) . . . . ?
C11 C12 C13 C14 -53.9(6) . . . . ?
C12 C13 C14 C15 54.8(6) . . . . ?
C13 C14 C15 C10 -57.1(6) . . . . ?
C15 C10 C11 C12 -53.1(5) . . . . ?
C16 N1 C10 C1 67.2(6) . . . . ?
C16 N1 C10 C11 -170.4(4) . . . . ?
C16 N1 C10 C15 -53.2(6) . . . . ?
C16 C17 C18 C19 -178.2(5) . . . . ?
C16 C17 C22 C21 179.2(5) . . . . ?
C17 C18 C19 C20 -0.5(9) . . . . ?
C18 C17 C22 C21 1.6(8) . . . . ?
C18 C19 C20 Br1 179.2(4) . . . . ?
C18 C19 C20 C21 0.6(9) . . . . ?
C19 C20 C21 C22 0.4(10) . . . . ?
C20 C21 C22 C17 -1.5(9) . . . . ?
C22 C17 C18 C19 -0.6(9) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.838 524.3 36.7 ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_d8v19809_0m
_database_code_depnum_ccdc_archive 'CCDC 1992438'
loop_
_audit_author_name
_audit_author_address
'Changhua Ding'
;Shanghai University
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N'
_chemical_formula_weight         239.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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                   6.06320(10)
_cell_length_b                   31.1441(6)
_cell_length_c                   11.8320(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.5730(10)
_cell_angle_gamma                90
_cell_volume                     2171.87(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      5.675
_cell_measurement_theta_max      140.179

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.474
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34262
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         66.985
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             7552
_reflns_number_gt                7176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.959

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0488P)²+0.1304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0110(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3321 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.13(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7552
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.8625(4) 0.31226(8) 0.5142(2) 0.0624(5) Uani 1 1 d . . . . .
C1 C 0.6552(4) 0.29727(7) 0.54701(19) 0.0525(5) Uani 1 1 d . . . . .
C2 C 0.4435(5) 0.31194(10) 0.4569(2) 0.0703(7) Uani 1 1 d . . . . .
H2A H 0.4467 0.3426 0.4486 0.106 Uiso 1 1 calc R U . . .
H2B H 0.3101 0.3038 0.4822 0.106 Uiso 1 1 calc R U . . .
H2C H 0.4411 0.2986 0.3834 0.106 Uiso 1 1 calc R U . . .
C3 C 0.6618(4) 0.31559(7) 0.67141(19) 0.0502(5) Uani 1 1 d . . . . .
H3 H 0.7994 0.3039 0.7228 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4637(4) 0.30027(8) 0.7208(2) 0.0595(6) Uani 1 1 d . . . . .
H4A H 0.3248 0.3132 0.6764 0.071 Uiso 1 1 calc R U . . .
H4B H 0.4489 0.2694 0.7111 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4902(7) 0.31101(10) 0.8477(3) 0.0845(9) Uani 1 1 d . . . . .
H5A H 0.4889 0.3416 0.8571 0.127 Uiso 1 1 calc R U . . .
H5B H 0.6314 0.2997 0.8919 0.127 Uiso 1 1 calc R U . . .
H5C H 0.3671 0.2986 0.8748 0.127 Uiso 1 1 calc R U . . .
C6 C 0.6887(4) 0.36423(7) 0.67711(19) 0.0510(5) Uani 1 1 d . . . . .
C7 C 0.5073(4) 0.39208(8) 0.6395(2) 0.0601(6) Uani 1 1 d . . . . .
H7 H 0.3625 0.3809 0.6111 0.072 Uiso 1 1 calc R U . . .
C8 C 0.5383(5) 0.43600(8) 0.6435(3) 0.0697(7) Uani 1 1 d . . . . .
H8 H 0.4148 0.4540 0.6168 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7495(5) 0.45338(8) 0.6866(2) 0.0706(7) Uani 1 1 d . . . . .
H9 H 0.7695 0.4830 0.6892 0.085 Uiso 1 1 calc R U . . .
C10 C 0.9308(5) 0.42645(9) 0.7257(2) 0.0694(7) Uani 1 1 d . . . . .
H10 H 1.0745 0.4379 0.7553 0.083 Uiso 1 1 calc R U . . .
C11 C 0.9008(4) 0.38242(8) 0.7214(2) 0.0601(6) Uani 1 1 d . . . . .
H11 H 1.0250 0.3646 0.7487 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6726(4) 0.24818(8) 0.5564(2) 0.0572(6) Uani 1 1 d . . . . .
C13 C 0.8791(5) 0.22913(8) 0.6052(3) 0.0711(7) Uani 1 1 d . . . . .
H13 H 1.0059 0.2464 0.6312 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9019(6) 0.18508(10) 0.6162(3) 0.0902(9) Uani 1 1 d . . . . .
H14 H 1.0433 0.1731 0.6484 0.108 Uiso 1 1 calc R U . . .
C15 C 0.7181(8) 0.15910(11) 0.5801(3) 0.0965(11) Uani 1 1 d . . . . .
H15 H 0.7330 0.1295 0.5877 0.116 Uiso 1 1 calc R U . . .
C16 C 0.5130(7) 0.17694(12) 0.5327(3) 0.0949(11) Uani 1 1 d . . . . .
H16 H 0.3873 0.1592 0.5080 0.114 Uiso 1 1 calc R U . . .
C17 C 0.4873(5) 0.22126(10) 0.5204(3) 0.0743(7) Uani 1 1 d . . . . .
H17 H 0.3452 0.2328 0.4878 0.089 Uiso 1 1 calc R U . . .
N2 N 0.3562(3) 0.54151(8) 0.25526(18) 0.0611(5) Uani 1 1 d . . . . .
C18 C 0.5972(3) 0.53582(7) 0.31599(17) 0.0465(4) Uani 1 1 d . . . . .
C19 C 0.7506(5) 0.56257(8) 0.2574(2) 0.0624(6) Uani 1 1 d . . . . .
H19A H 0.7138 0.5568 0.1754 0.094 Uiso 1 1 calc R U . . .
H19B H 0.9063 0.5552 0.2899 0.094 Uiso 1 1 calc R U . . .
H19C H 0.7278 0.5925 0.2701 0.094 Uiso 1 1 calc R U . . .
C20 C 0.6471(3) 0.48644(6) 0.31437(17) 0.0451(4) Uani 1 1 d . . . . .
H20 H 0.5404 0.4725 0.3534 0.054 Uiso 1 1 calc R U . . .
C21 C 0.8852(4) 0.47388(7) 0.38364(19) 0.0535(5) Uani 1 1 d . . . . .
H21A H 0.9967 0.4850 0.3443 0.064 Uiso 1 1 calc R U . . .
H21B H 0.9133 0.4870 0.4600 0.064 Uiso 1 1 calc R U . . .
C22 C 0.9148(6) 0.42556(9) 0.3975(3) 0.0803(8) Uani 1 1 d . . . . .
H22A H 0.8926 0.4125 0.3222 0.120 Uiso 1 1 calc R U . . .
H22B H 0.8053 0.4144 0.4368 0.120 Uiso 1 1 calc R U . . .
H22C H 1.0650 0.4193 0.4423 0.120 Uiso 1 1 calc R U . . .
C23 C 0.5982(4) 0.46796(6) 0.19188(17) 0.0469(5) Uani 1 1 d . . . . .
C24 C 0.4001(4) 0.44489(8) 0.1478(2) 0.0587(6) Uani 1 1 d . . . . .
H24 H 0.2962 0.4410 0.1936 0.070 Uiso 1 1 calc R U . . .
C25 C 0.3552(5) 0.42770(9) 0.0369(2) 0.0716(7) Uani 1 1 d . . . . .
H25 H 0.2224 0.4122 0.0090 0.086 Uiso 1 1 calc R U . . .
C26 C 0.5068(5) 0.43343(9) -0.0326(2) 0.0704(7) Uani 1 1 d . . . . .
H26 H 0.4757 0.4222 -0.1075 0.084 Uiso 1 1 calc R U . . .
C27 C 0.7028(5) 0.45574(8) 0.0094(2) 0.0668(7) Uani 1 1 d . . . . .
H27 H 0.8056 0.4595 -0.0371 0.080 Uiso 1 1 calc R U . . .
C28 C 0.7498(4) 0.47279(8) 0.1205(2) 0.0563(5) Uani 1 1 d . . . . .
H28 H 0.8846 0.4877 0.1479 0.068 Uiso 1 1 calc R U . . .
C29 C 0.6199(3) 0.54993(6) 0.44234(18) 0.0445(4) Uani 1 1 d . . . . .
C30 C 0.8154(4) 0.56911(8) 0.5077(2) 0.0568(5) Uani 1 1 d . . . . .
H30 H 0.9366 0.5743 0.4738 0.068 Uiso 1 1 calc R U . . .
C31 C 0.8327(5) 0.58058(8) 0.6228(2) 0.0668(7) Uani 1 1 d . . . . .
H31 H 0.9665 0.5926 0.6659 0.080 Uiso 1 1 calc R U . . .
C32 C 0.6547(5) 0.57426(8) 0.6733(2) 0.0660(7) Uani 1 1 d . . . . .
H32 H 0.6650 0.5829 0.7496 0.079 Uiso 1 1 calc R U . . .
C33 C 0.4606(5) 0.55517(8) 0.6107(2) 0.0620(6) Uani 1 1 d . . . . .
H33 H 0.3397 0.5504 0.6451 0.074 Uiso 1 1 calc R U . . .
C34 C 0.4437(4) 0.54295(7) 0.49691(19) 0.0515(5) Uani 1 1 d . . . . .
H34 H 0.3114 0.5298 0.4559 0.062 Uiso 1 1 calc R U . . .
N3 N -0.1423(4) 0.68733(8) 0.7885(2) 0.0647(5) Uani 1 1 d . . . . .
C35 C 0.0953(4) 0.70267(7) 0.8246(2) 0.0521(5) Uani 1 1 d . . . . .
C36 C 0.2266(5) 0.69015(9) 0.7344(2) 0.0670(6) Uani 1 1 d . . . . .
H36A H 0.2171 0.6597 0.7224 0.101 Uiso 1 1 calc R U . . .
H36B H 0.3827 0.6984 0.7616 0.101 Uiso 1 1 calc R U . . .
H36C H 0.1627 0.7045 0.6624 0.101 Uiso 1 1 calc R U . . .
C37 C 0.2009(4) 0.68241(7) 0.94661(19) 0.0524(5) Uani 1 1 d . . . . .
H37 H 0.1062 0.6922 0.9982 0.063 Uiso 1 1 calc R U . . .
C38 C 0.4414(4) 0.69841(8) 1.0011(2) 0.0637(6) Uani 1 1 d . . . . .
H38A H 0.5441 0.6873 0.9563 0.076 Uiso 1 1 calc R U . . .
H38B H 0.4435 0.7295 0.9962 0.076 Uiso 1 1 calc R U . . .
C39 C 0.5266(7) 0.68521(13) 1.1265(3) 0.1022(11) Uani 1 1 d . . . . .
H39A H 0.5366 0.6545 1.1314 0.153 Uiso 1 1 calc R U . . .
H39B H 0.4235 0.6953 1.1710 0.153 Uiso 1 1 calc R U . . .
H39C H 0.6740 0.6974 1.1568 0.153 Uiso 1 1 calc R U . . .
C40 C 0.1870(4) 0.63358(7) 0.94585(18) 0.0492(5) Uani 1 1 d . . . . .
C41 C 0.3453(4) 0.60773(8) 0.9104(2) 0.0584(5) Uani 1 1 d . . . . .
H41 H 0.4655 0.6205 0.8866 0.070 Uiso 1 1 calc R U . . .
C42 C 0.3277(5) 0.56347(8) 0.9098(2) 0.0636(6) Uani 1 1 d . . . . .
H42 H 0.4369 0.5468 0.8868 0.076 Uiso 1 1 calc R U . . .
C43 C 0.1493(5) 0.54389(8) 0.9432(2) 0.0652(6) Uani 1 1 d . . . . .
H43 H 0.1358 0.5141 0.9412 0.078 Uiso 1 1 calc R U . . .
C44 C -0.0078(5) 0.56860(9) 0.9792(2) 0.0651(6) Uani 1 1 d . . . . .
H44 H -0.1285 0.5556 1.0019 0.078 Uiso 1 1 calc R U . . .
C45 C 0.0120(4) 0.61298(8) 0.9821(2) 0.0573(5) Uani 1 1 d . . . . .
H45 H -0.0939 0.6293 1.0087 0.069 Uiso 1 1 calc R U . . .
C46 C 0.0843(4) 0.75154(8) 0.8385(2) 0.0547(5) Uani 1 1 d . . . . .
C47 C -0.0797(5) 0.76977(9) 0.8874(3) 0.0705(7) Uani 1 1 d . . . . .
H47 H -0.1833 0.7520 0.9113 0.085 Uiso 1 1 calc R U . . .
C48 C -0.0938(6) 0.81353(10) 0.9018(3) 0.0856(9) Uani 1 1 d . . . . .
H48 H -0.2068 0.8249 0.9341 0.103 Uiso 1 1 calc R U . . .
C49 C 0.0599(6) 0.84038(10) 0.8681(3) 0.0844(9) Uani 1 1 d . . . . .
H49 H 0.0510 0.8699 0.8774 0.101 Uiso 1 1 calc R U . . .
C50 C 0.2241(6) 0.82333(10) 0.8214(3) 0.0826(8) Uani 1 1 d . . . . .
H50 H 0.3285 0.8413 0.7989 0.099 Uiso 1 1 calc R U . . .
C51 C 0.2379(5) 0.77935(9) 0.8068(2) 0.0694(7) Uani 1 1 d . . . . .
H51 H 0.3525 0.7683 0.7751 0.083 Uiso 1 1 calc R U . . .
H1A H 0.871(5) 0.3406(12) 0.511(3) 0.082(9) Uiso 1 1 d . . . . .
H2D H 0.340(5) 0.5331(10) 0.179(3) 0.076(8) Uiso 1 1 d . . . . .
H1B H 0.866(5) 0.3002(11) 0.445(3) 0.088(10) Uiso 1 1 d . . . . .
H3A H -0.131(6) 0.6571(12) 0.770(3) 0.093(10) Uiso 1 1 d . . . . .
H3B H -0.214(7) 0.7019(13) 0.713(4) 0.119(13) Uiso 1 1 d . . . . .
H2E H 0.325(6) 0.5705(12) 0.251(3) 0.089(10) Uiso 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 C1 1.476(3) . ?
N1 H1A 0.89(4) . ?
N1 H1B 0.91(4) . ?
C1 C2 1.533(3) . ?
C1 C12 1.535(3) . ?
C1 C3 1.570(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C6 1.523(3) . ?
C3 C4 1.530(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.390(3) . ?
C6 C11 1.391(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.383(4) . ?
C12 C17 1.386(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N2 C18 1.480(3) . ?
N2 H2D 0.92(3) . ?
N2 H2E 0.92(4) . ?
C18 C19 1.530(3) . ?
C18 C29 1.533(3) . ?
C18 C20 1.568(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C23 1.522(3) . ?
C20 C21 1.534(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.392(3) . ?
C23 C28 1.395(3) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.389(3) . ?
C29 C34 1.389(3) . ?
C30 C31 1.388(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.365(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.370(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N3 C35 1.482(3) . ?
N3 H3A 0.97(4) . ?
N3 H3B 1.01(4) . ?
C35 C36 1.523(3) . ?
C35 C46 1.534(3) . ?
C35 C37 1.568(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C40 1.523(3) . ?
C37 C38 1.533(3) . ?
C37 H37 0.9800 . ?
C38 C39 1.509(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C45 1.391(3) . ?
C40 C41 1.391(3) . ?
C41 C42 1.382(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.378(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.368(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.387(4) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 C47 1.385(4) . ?
C46 C51 1.386(3) . ?
C47 C48 1.379(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.379(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.356(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.386(4) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?

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
C1 N1 H1A 113(2) . . ?
C1 N1 H1B 108(2) . . ?
H1A N1 H1B 111(3) . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 C12 106.61(19) . . ?
C2 C1 C12 112.3(2) . . ?
N1 C1 C3 107.18(19) . . ?
C2 C1 C3 112.13(19) . . ?
C12 C1 C3 107.93(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C3 C4 112.24(18) . . ?
C6 C3 C1 112.45(18) . . ?
C4 C3 C1 113.25(18) . . ?
C6 C3 H3 106.1 . . ?
C4 C3 H3 106.1 . . ?
C1 C3 H3 106.1 . . ?
C5 C4 C3 113.6(2) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 117.3(2) . . ?
C7 C6 C3 122.6(2) . . ?
C11 C6 C3 120.1(2) . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C13 C12 C17 117.2(3) . . ?
C13 C12 C1 119.9(2) . . ?
C17 C12 C1 122.9(2) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 120.3(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 N2 H2D 107.7(19) . . ?
C18 N2 H2E 108(2) . . ?
H2D N2 H2E 105(3) . . ?
N2 C18 C19 110.51(19) . . ?
N2 C18 C29 106.95(17) . . ?
C19 C18 C29 111.13(19) . . ?
N2 C18 C20 106.43(18) . . ?
C19 C18 C20 112.89(17) . . ?
C29 C18 C20 108.64(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C21 111.16(17) . . ?
C23 C20 C18 112.78(16) . . ?
C21 C20 C18 113.79(16) . . ?
C23 C20 H20 106.1 . . ?
C21 C20 H20 106.1 . . ?
C18 C20 H20 106.1 . . ?
C22 C21 C20 112.5(2) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 117.5(2) . . ?
C24 C23 C20 120.68(19) . . ?
C28 C23 C20 121.80(19) . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 119.5(2) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C30 C29 C34 117.2(2) . . ?
C30 C29 C18 122.38(19) . . ?
C34 C29 C18 120.36(19) . . ?
C31 C30 C29 121.0(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 119.6(2) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C32 C33 C34 120.3(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C29 121.4(2) . . ?
C33 C34 H34 119.3 . . ?
C29 C34 H34 119.3 . . ?
C35 N3 H3A 105(2) . . ?
C35 N3 H3B 107(2) . . ?
H3A N3 H3B 106(3) . . ?
N3 C35 C36 110.4(2) . . ?
N3 C35 C46 106.67(19) . . ?
C36 C35 C46 111.85(19) . . ?
N3 C35 C37 107.14(18) . . ?
C36 C35 C37 111.98(19) . . ?
C46 C35 C37 108.58(18) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C40 C37 C38 111.92(19) . . ?
C40 C37 C35 112.71(18) . . ?
C38 C37 C35 113.50(19) . . ?
C40 C37 H37 106.0 . . ?
C38 C37 H37 106.0 . . ?
C35 C37 H37 106.0 . . ?
C39 C38 C37 113.4(3) . . ?
C39 C38 H38A 108.9 . . ?
C37 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C37 C38 H38B 108.9 . . ?
H38A C38 H38B 107.7 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 117.1(2) . . ?
C45 C40 C37 120.3(2) . . ?
C41 C40 C37 122.6(2) . . ?
C42 C41 C40 121.4(2) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C43 C42 C41 120.3(2) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C44 C43 C42 119.4(2) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 120.4(2) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C44 C45 C40 121.3(2) . . ?
C44 C45 H45 119.3 . . ?
C40 C45 H45 119.3 . . ?
C47 C46 C51 116.8(2) . . ?
C47 C46 C35 120.4(2) . . ?
C51 C46 C35 122.8(2) . . ?
C48 C47 C46 121.9(3) . . ?
C48 C47 H47 119.1 . . ?
C46 C47 H47 119.1 . . ?
C47 C48 C49 119.9(3) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C50 C49 C48 119.4(3) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C49 C50 C51 120.7(3) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C50 C51 C46 121.3(3) . . ?
C50 C51 H51 119.3 . . ?
C46 C51 H51 119.3 . . ?

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 C3 C6 55.2(2) . . . . ?
C2 C1 C3 C6 -66.1(3) . . . . ?
C12 C1 C3 C6 169.64(18) . . . . ?
N1 C1 C3 C4 -176.30(19) . . . . ?
C2 C1 C3 C4 62.4(3) . . . . ?
C12 C1 C3 C4 -61.8(2) . . . . ?
C6 C3 C4 C5 -61.7(3) . . . . ?
C1 C3 C4 C5 169.6(2) . . . . ?
C4 C3 C6 C7 -48.2(3) . . . . ?
C1 C3 C6 C7 80.9(3) . . . . ?
C4 C3 C6 C11 131.7(2) . . . . ?
C1 C3 C6 C11 -99.2(2) . . . . ?
C11 C6 C7 C8 1.5(4) . . . . ?
C3 C6 C7 C8 -178.6(2) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 -1.2(4) . . . . ?
C3 C6 C11 C10 178.8(2) . . . . ?
N1 C1 C12 C13 39.6(3) . . . . ?
C2 C1 C12 C13 160.6(2) . . . . ?
C3 C1 C12 C13 -75.2(3) . . . . ?
N1 C1 C12 C17 -142.0(2) . . . . ?
C2 C1 C12 C17 -21.0(3) . . . . ?
C3 C1 C12 C17 103.1(2) . . . . ?
C17 C12 C13 C14 1.0(4) . . . . ?
C1 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C1 C12 C17 C16 -179.0(3) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
N2 C18 C20 C23 57.4(2) . . . . ?
C19 C18 C20 C23 -64.0(2) . . . . ?
C29 C18 C20 C23 172.28(17) . . . . ?
N2 C18 C20 C21 -174.76(17) . . . . ?
C19 C18 C20 C21 63.8(2) . . . . ?
C29 C18 C20 C21 -59.9(2) . . . . ?
C23 C20 C21 C22 -61.0(3) . . . . ?
C18 C20 C21 C22 170.4(2) . . . . ?
C21 C20 C23 C24 129.1(2) . . . . ?
C18 C20 C23 C24 -101.7(2) . . . . ?
C21 C20 C23 C28 -49.9(3) . . . . ?
C18 C20 C23 C28 79.3(2) . . . . ?
C28 C23 C24 C25 -0.4(4) . . . . ?
C20 C23 C24 C25 -179.5(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 -0.5(4) . . . . ?
C24 C23 C28 C27 0.9(3) . . . . ?
C20 C23 C28 C27 179.9(2) . . . . ?
N2 C18 C29 C30 -147.2(2) . . . . ?
C19 C18 C29 C30 -26.5(3) . . . . ?
C20 C18 C29 C30 98.3(2) . . . . ?
N2 C18 C29 C34 34.2(3) . . . . ?
C19 C18 C29 C34 154.9(2) . . . . ?
C20 C18 C29 C34 -80.3(2) . . . . ?
C34 C29 C30 C31 0.2(3) . . . . ?
C18 C29 C30 C31 -178.4(2) . . . . ?
C29 C30 C31 C32 -1.8(4) . . . . ?
C30 C31 C32 C33 2.2(4) . . . . ?
C31 C32 C33 C34 -0.9(4) . . . . ?
C32 C33 C34 C29 -0.7(4) . . . . ?
C30 C29 C34 C33 1.0(3) . . . . ?
C18 C29 C34 C33 179.7(2) . . . . ?
N3 C35 C37 C40 56.5(2) . . . . ?
C36 C35 C37 C40 -64.6(2) . . . . ?
C46 C35 C37 C40 171.39(18) . . . . ?
N3 C35 C37 C38 -174.9(2) . . . . ?
C36 C35 C37 C38 63.9(3) . . . . ?
C46 C35 C37 C38 -60.1(2) . . . . ?
C40 C37 C38 C39 -61.3(3) . . . . ?
C35 C37 C38 C39 169.7(2) . . . . ?
C38 C37 C40 C45 133.5(2) . . . . ?
C35 C37 C40 C45 -97.1(2) . . . . ?
C38 C37 C40 C41 -46.1(3) . . . . ?
C35 C37 C40 C41 83.3(3) . . . . ?
C45 C40 C41 C42 0.8(3) . . . . ?
C37 C40 C41 C42 -179.6(2) . . . . ?
C40 C41 C42 C43 0.9(4) . . . . ?
C41 C42 C43 C44 -1.4(4) . . . . ?
C42 C43 C44 C45 0.1(4) . . . . ?
C43 C44 C45 C40 1.7(4) . . . . ?
C41 C40 C45 C44 -2.1(3) . . . . ?
C37 C40 C45 C44 178.2(2) . . . . ?
N3 C35 C46 C47 39.5(3) . . . . ?
C36 C35 C46 C47 160.3(2) . . . . ?
C37 C35 C46 C47 -75.6(3) . . . . ?
N3 C35 C46 C51 -142.3(2) . . . . ?
C36 C35 C46 C51 -21.5(3) . . . . ?
C37 C35 C46 C51 102.5(3) . . . . ?
C51 C46 C47 C48 1.4(4) . . . . ?
C35 C46 C47 C48 179.7(3) . . . . ?
C46 C47 C48 C49 -0.7(5) . . . . ?
C47 C48 C49 C50 -0.2(5) . . . . ?
C48 C49 C50 C51 0.3(5) . . . . ?
C49 C50 C51 C46 0.5(5) . . . . ?
C47 C46 C51 C50 -1.3(4) . . . . ?
C35 C46 C51 C50 -179.5(3) . . . . ?

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd16696
_database_code_depnum_ccdc_archive 'CCDC 1992437'
loop_
_audit_author_name
_audit_author_address
'Changhua Ding'
;Shanghai University
China
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Br N O'
_chemical_formula_weight         398.33

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   12.7423(15)
_cell_length_b                   12.7423(15)
_cell_length_c                   22.890(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3218.7(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2018
_cell_measurement_theta_min      5.128
_cell_measurement_theta_max      34.333

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             1236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.924
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5688
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17759
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3759
_reflns_number_gt                2194
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.963

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1129P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 805 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.017(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3759
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2033
_refine_ls_wR_factor_gt          0.1840
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.203 0.519 0.255 30 9 ' '
2 0.316 0.797 0.921 29 9 ' '
3 0.481 0.684 0.588 29 9 ' '
4 0.519 0.316 0.088 29 9 ' '
5 0.684 0.203 0.421 29 9 ' '
6 0.796 0.481 0.755 30 9 ' '
_platon_squeeze_details          
;
;



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
Br1 Br 0.13466(18) 1.32173(11) 0.09335(12) 0.1355(9) Uani 1 1 d . . . . .
N1 N 0.0237(6) 0.7392(6) 0.1172(3) 0.0394(16) Uani 1 1 d D . . . .
O1 O -0.1154(6) 0.7139(6) 0.0498(3) 0.0579(16) Uani 1 1 d . . . . .
C1 C 0.0108(8) 0.6173(7) 0.1163(4) 0.047(2) Uani 1 1 d . . . . .
C2 C 0.1117(8) 0.6248(9) 0.1547(5) 0.057(2) Uani 1 1 d . . . . .
H2A H 0.1013 0.5444 0.1589 0.069 Uiso 1 1 calc R U . . .
H2B H 0.1054 0.6527 0.1933 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2363(9) 0.7090(10) 0.1303(4) 0.061(3) Uani 1 1 d . . . . .
H3A H 0.2500 0.7910 0.1305 0.073 Uiso 1 1 calc R U . . .
H3B H 0.2963 0.7072 0.1557 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2543(9) 0.6776(11) 0.0696(5) 0.078(3) Uani 1 1 d . . . . .
H4A H 0.2491 0.5991 0.0692 0.094 Uiso 1 1 calc R U . . .
H4B H 0.3336 0.7376 0.0552 0.094 Uiso 1 1 calc R U . . .
C5 C 0.1550(10) 0.6752(10) 0.0309(5) 0.072(3) Uani 1 1 d . . . . .
H5A H 0.1645 0.7555 0.0293 0.087 Uiso 1 1 calc R U . . .
H5B H 0.1628 0.6518 -0.0085 0.087 Uiso 1 1 calc R U . . .
C6 C 0.0310(8) 0.5865(9) 0.0546(4) 0.052(2) Uani 1 1 d . . . . .
H6A H 0.0209 0.5059 0.0545 0.062 Uiso 1 1 calc R U . . .
H6B H -0.0302 0.5856 0.0291 0.062 Uiso 1 1 calc R U . . .
C7 C -0.1193(8) 0.5220(7) 0.1369(4) 0.046(2) Uani 1 1 d . . . . .
H7 H -0.1743 0.5206 0.1065 0.056 Uiso 1 1 calc R U . . .
C8 C -0.1400(10) 0.3940(8) 0.1398(4) 0.061(3) Uani 1 1 d . . . . .
H8 H -0.0899 0.3807 0.1645 0.073 Uiso 1 1 calc R U . . .
C9 C -0.2193(14) 0.3043(10) 0.1117(6) 0.101(5) Uani 1 1 d . . . . .
H9A H -0.2714 0.3136 0.0866 0.121 Uiso 1 1 calc R U . . .
H9B H -0.2258 0.2287 0.1161 0.121 Uiso 1 1 calc R U . . .
C10 C -0.1617(8) 0.5516(8) 0.1939(4) 0.049(2) Uani 1 1 d . . . . .
C11 C -0.2385(11) 0.5970(10) 0.1923(5) 0.068(3) Uani 1 1 d . . . . .
H11 H -0.2647 0.6095 0.1564 0.082 Uiso 1 1 calc R U . . .
C12 C -0.2777(12) 0.6245(11) 0.2425(7) 0.088(4) Uani 1 1 d . . . . .
H12 H -0.3273 0.6587 0.2405 0.106 Uiso 1 1 calc R U . . .
C13 C -0.2444(13) 0.6020(12) 0.2950(7) 0.093(4) Uani 1 1 d . . . . .
H13 H -0.2725 0.6188 0.3292 0.112 Uiso 1 1 calc R U . . .
C14 C -0.1687(12) 0.5543(15) 0.2973(6) 0.100(5) Uani 1 1 d . . . . .
H14 H -0.1478 0.5360 0.3333 0.120 Uiso 1 1 calc R U . . .
C15 C -0.1240(9) 0.5334(10) 0.2467(5) 0.074(3) Uani 1 1 d . . . . .
H15 H -0.0680 0.5069 0.2485 0.089 Uiso 1 1 calc R U . . .
C16 C -0.0338(7) 0.7779(7) 0.0844(4) 0.0390(19) Uani 1 1 d . . . . .
C17 C 0.0094(8) 0.9112(7) 0.0876(4) 0.0433(19) Uani 1 1 d . . . . .
C18 C -0.0740(9) 0.9477(9) 0.0804(5) 0.067(3) Uani 1 1 d . . . . .
H18 H -0.1552 0.8911 0.0743 0.080 Uiso 1 1 calc R U . . .
C19 C -0.0344(12) 1.0736(10) 0.0824(7) 0.084(4) Uani 1 1 d . . . . .
H19 H -0.0905 1.0995 0.0782 0.101 Uiso 1 1 calc R U . . .
C20 C 0.0811(12) 1.1540(9) 0.0900(6) 0.077(3) Uani 1 1 d . . . . .
C21 C 0.1687(10) 1.1190(8) 0.0968(5) 0.074(3) Uani 1 1 d . . . . .
H21 H 0.2503 1.1762 0.1013 0.089 Uiso 1 1 calc R U . . .
C22 C 0.1292(9) 0.9963(8) 0.0966(5) 0.061(3) Uani 1 1 d . . . . .
H22 H 0.1851 0.9707 0.1026 0.073 Uiso 1 1 calc R U . . .
H1 H 0.076(5) 0.789(5) 0.140(3) 0.03(2) Uiso 1 1 d 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
Br1 C20 1.892(10) . ?
N1 C16 1.305(10) . ?
N1 C1 1.479(10) . ?
N1 H1 0.84(3) . ?
O1 C16 1.236(10) . ?
C1 C2 1.520(13) . ?
C1 C6 1.522(13) . ?
C1 C7 1.559(12) . ?
C2 C3 1.511(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.494(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.532(15) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.511(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.518(13) . ?
C7 C10 1.530(13) . ?
C7 H7 0.9800 . ?
C8 C9 1.259(15) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.365(15) . ?
C10 C15 1.363(14) . ?
C11 C12 1.367(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.35(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.37(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.503(11) . ?
C17 C18 1.366(12) . ?
C17 C22 1.377(12) . ?
C18 C19 1.421(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.319(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(16) . ?
C21 C22 1.382(13) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C16 N1 C1 126.9(7) . . ?
C16 N1 H1 118(5) . . ?
C1 N1 H1 115(5) . . ?
N1 C1 C2 106.3(7) . . ?
N1 C1 C6 109.8(7) . . ?
C2 C1 C6 107.8(7) . . ?
N1 C1 C7 109.3(7) . . ?
C2 C1 C7 114.3(7) . . ?
C6 C1 C7 109.3(7) . . ?
C1 C2 C3 112.8(8) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.6(9) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 108.0(8) . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C4 110.6(9) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 112.9(8) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C10 109.5(7) . . ?
C8 C7 C1 113.3(7) . . ?
C10 C7 C1 115.7(7) . . ?
C8 C7 H7 105.8 . . ?
C10 C7 H7 105.8 . . ?
C1 C7 H7 105.8 . . ?
C9 C8 C7 125.6(11) . . ?
C9 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C11 C10 C15 119.0(10) . . ?
C11 C10 C7 119.8(9) . . ?
C15 C10 C7 121.1(9) . . ?
C10 C11 C12 121.1(12) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.0(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.5(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.9(12) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O1 C16 N1 124.5(7) . . ?
O1 C16 C17 119.2(7) . . ?
N1 C16 C17 116.2(7) . . ?
C18 C17 C22 119.6(8) . . ?
C18 C17 C16 118.1(8) . . ?
C22 C17 C16 122.2(7) . . ?
C17 C18 C19 118.9(10) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.6(10) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 121.6(9) . . ?
C19 C20 Br1 121.0(8) . . ?
C21 C20 Br1 117.4(9) . . ?
C22 C21 C20 117.5(10) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C21 C22 C17 121.7(9) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?

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
C16 N1 C1 C2 170.5(8) . . . . ?
C16 N1 C1 C6 54.1(10) . . . . ?
C16 N1 C1 C7 -65.7(10) . . . . ?
N1 C1 C2 C3 -64.9(9) . . . . ?
C6 C1 C2 C3 52.7(9) . . . . ?
C7 C1 C2 C3 174.4(7) . . . . ?
C1 C2 C3 C4 -56.1(11) . . . . ?
C2 C3 C4 C5 55.9(12) . . . . ?
C3 C4 C5 C6 -56.9(12) . . . . ?
C4 C5 C6 C1 59.7(11) . . . . ?
N1 C1 C6 C5 59.7(10) . . . . ?
C2 C1 C6 C5 -55.7(10) . . . . ?
C7 C1 C6 C5 179.5(8) . . . . ?
N1 C1 C7 C8 -177.8(7) . . . . ?
C2 C1 C7 C8 -58.8(10) . . . . ?
C6 C1 C7 C8 62.1(9) . . . . ?
N1 C1 C7 C10 -50.0(10) . . . . ?
C2 C1 C7 C10 68.9(10) . . . . ?
C6 C1 C7 C10 -170.2(8) . . . . ?
C10 C7 C8 C9 108.5(12) . . . . ?
C1 C7 C8 C9 -120.6(12) . . . . ?
C8 C7 C10 C11 -129.0(9) . . . . ?
C1 C7 C10 C11 101.4(10) . . . . ?
C8 C7 C10 C15 51.0(11) . . . . ?
C1 C7 C10 C15 -78.6(11) . . . . ?
C15 C10 C11 C12 0.1(16) . . . . ?
C7 C10 C11 C12 -179.9(10) . . . . ?
C10 C11 C12 C13 -2.8(18) . . . . ?
C11 C12 C13 C14 2(2) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C11 C10 C15 C14 3.7(15) . . . . ?
C7 C10 C15 C14 -176.3(10) . . . . ?
C13 C14 C15 C10 -4.9(18) . . . . ?
C1 N1 C16 O1 5.3(13) . . . . ?
C1 N1 C16 C17 -171.1(7) . . . . ?
O1 C16 C17 C18 35.7(12) . . . . ?
N1 C16 C17 C18 -147.7(9) . . . . ?
O1 C16 C17 C22 -143.2(9) . . . . ?
N1 C16 C17 C22 33.4(13) . . . . ?
C22 C17 C18 C19 -0.1(16) . . . . ?
C16 C17 C18 C19 -179.0(10) . . . . ?
C17 C18 C19 C20 1.2(19) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C18 C19 C20 Br1 -179.5(10) . . . . ?
C19 C20 C21 C22 -1.4(19) . . . . ?
Br1 C20 C21 C22 177.6(9) . . . . ?
C20 C21 C22 C17 2.6(18) . . . . ?
C18 C17 C22 C21 -1.9(17) . . . . ?
C16 C17 C22 C21 177.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O1 0.98 2.54 3.136(11) 118.8 .
C6 H6B O1 0.97 2.42 3.025(11) 120.2 .
C7 H7 O1 0.98 2.54 3.136(11) 118.8 .
C6 H6B O1 0.97 2.42 3.025(11) 120.2 .
C7 H7 O1 0.98 2.54 3.136(11) 118.8 .
C6 H6B O1 0.97 2.42 3.025(11) 120.2 .
C6 H6B O1 0.97 2.42 3.025(11) 120.2 .
C7 H7 O1 0.98 2.54 3.136(11) 118.8 .

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-4

