# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_ddz21131_0m
_database_code_depnum_ccdc_archive 'CCDC 2163784'
loop_
_audit_author_name
_audit_author_address
'Chang-Hong Liu'
;Fudan University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        10
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Br N O'
_chemical_formula_weight         280.16

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.1547(3)
_cell_length_b                   8.9527(5)
_cell_length_c                   27.1544(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1253.13(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2213
_cell_measurement_theta_min      4.791
_cell_measurement_theta_max      50.462

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.259
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4201
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6238
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2443
_reflns_number_gt                1814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.988

_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)+(0.0356P)²+0.0639P] 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       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.015(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2443
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Br1 Br 0.13961(16) 0.48886(9) 0.45477(2) 0.1224(4) Uani 1 1 d . . . . .
O1 O 0.8953(5) 0.9010(3) 0.72862(11) 0.0500(7) Uani 1 1 d . . . . .
H1 H 1.0422 0.9350 0.7255 0.075 Uiso 1 1 calc R U . . .
N1 N 0.6385(6) 0.5628(3) 0.78576(11) 0.0362(7) Uani 1 1 d . . . . .
C1 C 0.2058(10) 0.6730(6) 0.59352(18) 0.0691(13) Uani 1 1 d . . . . .
H1B H 0.1181 0.7451 0.6117 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1254(11) 0.6386(6) 0.54616(19) 0.0774(15) Uani 1 1 d . . . . .
H2 H -0.0153 0.6885 0.5324 0.093 Uiso 1 1 calc R U . . .
C3 C 0.2520(11) 0.5318(6) 0.51962(17) 0.0708(14) Uani 1 1 d . . . . .
C4 C 0.4547(12) 0.4580(7) 0.53855(18) 0.0810(16) Uani 1 1 d . . . . .
H4 H 0.5387 0.3846 0.5203 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5384(10) 0.4928(6) 0.58611(16) 0.0729(14) Uani 1 1 d . . . . .
H5 H 0.6799 0.4423 0.5993 0.088 Uiso 1 1 calc R U . . .
C6 C 0.4162(9) 0.5998(5) 0.61370(14) 0.0512(10) Uani 1 1 d . . . . .
C7 C 0.5018(8) 0.6341(5) 0.66296(15) 0.0496(11) Uani 1 1 d . . . . .
C8 C 0.5670(7) 0.6613(4) 0.70407(14) 0.0402(9) Uani 1 1 d . . . . .
C9 C 0.6369(6) 0.6978(4) 0.75480(13) 0.0331(8) Uani 1 1 d . . . . .
H9 H 0.5066 0.7669 0.7679 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9036(6) 0.7719(4) 0.75893(13) 0.0344(8) Uani 1 1 d . . . . .
H10 H 1.0375 0.7034 0.7469 0.041 Uiso 1 1 calc R U . . .
C11 C 0.9563(7) 0.8108(4) 0.81197(14) 0.0439(10) Uani 1 1 d . . . . .
H11A H 0.8374 0.8888 0.8223 0.053 Uiso 1 1 calc R U . . .
H11B H 1.1313 0.8496 0.8149 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9261(8) 0.6768(5) 0.84600(14) 0.0485(10) Uani 1 1 d . . . . .
H12A H 1.0649 0.6061 0.8398 0.058 Uiso 1 1 calc R U . . .
H12B H 0.9395 0.7094 0.8800 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6668(7) 0.6009(5) 0.83806(14) 0.0443(9) Uani 1 1 d . . . . .
H13A H 0.6571 0.5109 0.8579 0.053 Uiso 1 1 calc R U . . .
H13B H 0.5275 0.6671 0.8481 0.053 Uiso 1 1 calc R U . . .
H1A H 0.503(9) 0.520(5) 0.7838(15) 0.055(13) 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
Br1 C3 1.893(5) . ?
O1 C10 1.420(4) . ?
O1 H1 0.8200 . ?
N1 C13 1.468(5) . ?
N1 C9 1.472(4) . ?
N1 H1A 0.80(4) . ?
C1 C6 1.381(6) . ?
C1 C2 1.386(6) . ?
C1 H1B 0.9300 . ?
C2 C3 1.363(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.339(8) . ?
C4 C5 1.397(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(5) . ?
C7 C8 1.191(5) . ?
C8 C9 1.461(5) . ?
C9 C10 1.531(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.506(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.522(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C10 O1 H1 109.5 . . ?
C13 N1 C9 111.3(3) . . ?
C13 N1 H1A 105(3) . . ?
C9 N1 H1A 111(3) . . ?
C6 C1 C2 119.9(5) . . ?
C6 C1 H1B 120.1 . . ?
C2 C1 H1B 120.1 . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 Br1 119.7(5) . . ?
C2 C3 Br1 119.2(4) . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 C7 121.1(4) . . ?
C1 C6 C7 120.5(4) . . ?
C8 C7 C6 178.5(4) . . ?
C7 C8 C9 177.6(4) . . ?
C8 C9 N1 110.9(3) . . ?
C8 C9 C10 112.8(3) . . ?
N1 C9 C10 108.0(3) . . ?
C8 C9 H9 108.4 . . ?
N1 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
O1 C10 C11 111.8(3) . . ?
O1 C10 C9 106.5(3) . . ?
C11 C10 C9 109.4(3) . . ?
O1 C10 H10 109.7 . . ?
C11 C10 H10 109.7 . . ?
C9 C10 H10 109.7 . . ?
C10 C11 C12 112.3(3) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.9(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
N1 C13 C12 109.2(3) . . ?
N1 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N1 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?

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
C6 C1 C2 C3 0.6(8) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C1 C2 C3 Br1 -179.4(4) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
Br1 C3 C4 C5 178.9(4) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 0.3(8) . . . . ?
C4 C5 C6 C7 179.3(5) . . . . ?
C2 C1 C6 C5 -0.8(7) . . . . ?
C2 C1 C6 C7 -179.9(5) . . . . ?
C13 N1 C9 C8 -170.8(3) . . . . ?
C13 N1 C9 C10 65.1(4) . . . . ?
C8 C9 C10 O1 57.0(4) . . . . ?
N1 C9 C10 O1 179.8(3) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
N1 C9 C10 C11 -59.2(3) . . . . ?
O1 C10 C11 C12 171.5(3) . . . . ?
C9 C10 C11 C12 53.8(4) . . . . ?
C10 C11 C12 C13 -51.8(4) . . . . ?
C9 N1 C13 C12 -62.8(4) . . . . ?
C11 C12 C13 N1 54.5(4) . . . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.045

_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_mo_d8v21878_0m
_database_code_depnum_ccdc_archive 'CCDC 2163800'
loop_
_audit_author_name
_audit_author_address
'Chang-Hong Liu'
;Fudan University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Br N O'
_chemical_formula_weight         266.14

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'

_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                   9.1212(3)
_cell_length_b                   5.4427(2)
_cell_length_c                   11.9771(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.8590(10)
_cell_angle_gamma                90
_cell_volume                     574.71(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3591
_cell_measurement_theta_min      6.457
_cell_measurement_theta_max      54.591

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.549
_shelx_estimated_absorpt_T_min   0.568
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            5679
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.244
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2216
_reflns_number_gt                2007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.971

_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)] 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       0.023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 799 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.027(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2216
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Br1 Br 0.11276(4) 0.05196(10) 0.76093(3) 0.0629(2) Uani 1 1 d . . . . .
O1 O 0.4445(3) 0.9797(3) 0.0906(2) 0.0406(6) Uani 1 1 d . . . . .
H1 H 0.4125 1.1228 0.0803 0.061 Uiso 1 1 calc R U . . .
N1 N 0.3474(3) 0.4594(4) 0.0642(2) 0.0340(6) Uani 1 1 d . . . . .
C1 C 0.1926(3) 0.5616(9) 0.0318(2) 0.0482(7) Uani 1 1 d . . . . .
H1B H 0.1226 0.4516 0.0574 0.058 Uiso 1 1 calc R U . . .
H1C H 0.1578 0.5794 -0.0523 0.058 Uiso 1 1 calc R U . . .
C2 C 0.1968(3) 0.8107(6) 0.0896(3) 0.0413(8) Uani 1 1 d . . . . .
H2A H 0.1304 0.8118 0.1423 0.050 Uiso 1 1 calc R U . . .
H2B H 0.1637 0.9401 0.0318 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3618(3) 0.8503(5) 0.1563(3) 0.0299(7) Uani 1 1 d . . . . .
H3 H 0.3693 0.9306 0.2317 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4231(3) 0.5863(6) 0.1715(2) 0.0286(6) Uani 1 1 d . . . . .
H4 H 0.5344 0.5855 0.1823 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3833(3) 0.4735(5) 0.2725(3) 0.0336(7) Uani 1 1 d . . . . .
C6 C 0.3412(4) 0.3983(6) 0.3514(2) 0.0334(7) Uani 1 1 d . . . . .
C7 C 0.2898(3) 0.3132(5) 0.4487(2) 0.0307(7) Uani 1 1 d . . . . .
C8 C 0.3235(4) 0.4454(6) 0.5512(2) 0.0355(7) Uani 1 1 d . . . . .
H8 H 0.3832 0.5880 0.5577 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2703(4) 0.3701(6) 0.6446(3) 0.0389(7) Uani 1 1 d . . . . .
H9 H 0.2920 0.4614 0.7135 0.047 Uiso 1 1 calc R U . . .
C10 C 0.1852(3) 0.1590(6) 0.6337(2) 0.0364(8) Uani 1 1 d . . . . .
C11 C 0.1502(3) 0.0243(7) 0.5336(2) 0.0394(8) Uani 1 1 d . . . . .
H11 H 0.0907 -0.1184 0.5280 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2033(3) 0.1002(6) 0.4412(2) 0.0377(8) Uani 1 1 d . . . . .
H12 H 0.1809 0.0074 0.3728 0.045 Uiso 1 1 calc R U . . .
H1A H 0.399(3) 0.490(5) 0.016(2) 0.032(9) 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
Br1 C10 1.902(3) . ?
O1 C3 1.410(3) . ?
O1 H1 0.8300 . ?
N1 C4 1.467(4) . ?
N1 C1 1.473(4) . ?
N1 H1A 0.85(3) . ?
C1 C2 1.519(6) . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.528(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.535(4) . ?
C3 H3 0.9900 . ?
C4 C5 1.482(4) . ?
C4 H4 0.9900 . ?
C5 C6 1.181(4) . ?
C6 C7 1.439(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.392(5) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.371(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

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
C3 O1 H1 109.5 . . ?
C4 N1 C1 104.9(2) . . ?
C4 N1 H1A 106.5(19) . . ?
C1 N1 H1A 114.1(19) . . ?
N1 C1 C2 107.9(3) . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
N1 C1 H1C 110.1 . . ?
C2 C1 H1C 110.1 . . ?
H1B C1 H1C 108.4 . . ?
C1 C2 C3 105.7(2) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
O1 C3 C2 112.0(3) . . ?
O1 C3 C4 107.7(2) . . ?
C2 C3 C4 102.1(2) . . ?
O1 C3 H3 111.5 . . ?
C2 C3 H3 111.5 . . ?
C4 C3 H3 111.5 . . ?
N1 C4 C5 111.2(3) . . ?
N1 C4 C3 105.1(2) . . ?
C5 C4 C3 109.1(2) . . ?
N1 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
C3 C4 H4 110.4 . . ?
C6 C5 C4 174.1(3) . . ?
C5 C6 C7 178.5(3) . . ?
C8 C7 C12 118.8(3) . . ?
C8 C7 C6 120.3(3) . . ?
C12 C7 C6 120.9(3) . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 Br1 119.1(2) . . ?
C9 C10 Br1 118.9(2) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

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
C4 N1 C1 C2 22.4(3) . . . . ?
N1 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 O1 92.8(3) . . . . ?
C1 C2 C3 C4 -22.1(3) . . . . ?
C1 N1 C4 C5 81.0(3) . . . . ?
C1 N1 C4 C3 -36.8(3) . . . . ?
O1 C3 C4 N1 -81.6(3) . . . . ?
C2 C3 C4 N1 36.5(3) . . . . ?
O1 C3 C4 C5 159.1(3) . . . . ?
C2 C3 C4 C5 -82.8(3) . . . . ?
C12 C7 C8 C9 -1.1(5) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C8 C9 C10 Br1 179.5(2) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
Br1 C10 C11 C12 -179.6(2) . . . . ?
C10 C11 C12 C7 -0.9(5) . . . . ?
C8 C7 C12 C11 1.0(5) . . . . ?
C6 C7 C12 C11 -177.8(3) . . . . ?

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
O1 H1 N1 0.83 1.92 2.749(3) 176.7 1_565
C2 H2A Br1 0.98 3.10 3.969(3) 149.2 2_556
C4 H4 Br1 0.99 3.12 4.105(3) 174.2 2_656
N1 H1A O1 0.85(3) 2.15(3) 2.976(3) 165(3) 2_645

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037

_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_d8v22017
_database_code_depnum_ccdc_archive 'CCDC 2163799'
loop_
_audit_author_name
_audit_author_address
'Chang-Hong Liu'
;Fudan University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Br N O3'
_chemical_formula_weight         442.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   20.352(6)
_cell_length_b                   9.238(3)
_cell_length_c                   24.982(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.392(7)
_cell_angle_gamma                90
_cell_volume                     4311(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3724
_cell_measurement_theta_min      4.918
_cell_measurement_theta_max      42.813

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4174
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15624
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3782
_reflns_number_gt                2057
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       '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)+(0.1272P)²+15.6619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.2676
_refine_ls_wR_factor_gt          0.2233
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Br1 Br 0.47685(6) 0.80095(11) 0.46480(5) 0.0993(5) Uani 1 1 d . . . . .
O1 O 0.1220(3) 0.4226(7) 0.6750(3) 0.0829(16) Uani 1 1 d . . . . .
H1 H 0.1350 0.4783 0.7028 0.124 Uiso 1 1 calc R U . . .
O2 O 0.3441(3) 0.0750(6) 0.7195(3) 0.0736(15) Uani 1 1 d . . . . .
O3 O 0.3278(2) 0.0811(6) 0.6237(2) 0.0670(13) Uani 1 1 d . . . . .
N1 N 0.2546(3) 0.2049(7) 0.6526(3) 0.0616(16) Uani 1 1 d . . . . .
C1 C 0.1652(5) 0.1510(10) 0.7560(4) 0.081(2) Uani 1 1 d . . . . .
H1A H 0.1839 0.2292 0.7809 0.097 Uiso 1 1 calc R U . . .
C2 C 0.1238(5) 0.0507(12) 0.7691(5) 0.097(3) Uani 1 1 d . . . . .
H2 H 0.1148 0.0610 0.8027 0.117 Uiso 1 1 calc R U . . .
C3 C 0.0960(5) -0.0636(11) 0.7327(5) 0.095(3) Uani 1 1 d . . . . .
H3 H 0.0678 -0.1314 0.7413 0.114 Uiso 1 1 calc R U . . .
C4 C 0.1092(5) -0.0789(10) 0.6839(4) 0.089(3) Uani 1 1 d . . . . .
H4 H 0.0899 -0.1569 0.6590 0.107 Uiso 1 1 calc R U . . .
C5 C 0.1510(4) 0.0204(9) 0.6710(3) 0.070(2) Uani 1 1 d . . . . .
H5 H 0.1602 0.0081 0.6377 0.084 Uiso 1 1 calc R U . . .
C6 C 0.1795(4) 0.1375(8) 0.7065(3) 0.0581(18) Uani 1 1 d . . . . .
C7 C 0.2239(4) 0.2518(8) 0.6935(3) 0.0581(18) Uani 1 1 d . . . . .
H7 H 0.2625 0.2825 0.7300 0.070 Uiso 1 1 calc R U . . .
C8 C 0.1806(4) 0.3874(8) 0.6610(3) 0.0649(19) Uani 1 1 d . . . . .
H8 H 0.2127 0.4710 0.6684 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1551(4) 0.3431(9) 0.5980(3) 0.067(2) Uani 1 1 d . . . . .
H9A H 0.1422 0.4271 0.5726 0.081 Uiso 1 1 calc R U . . .
H9B H 0.1140 0.2794 0.5872 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2188(4) 0.2645(9) 0.5941(3) 0.0641(19) Uani 1 1 d . . . . .
H10 H 0.2017 0.1853 0.5658 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2646(4) 0.3622(9) 0.5772(3) 0.0653(19) Uani 1 1 d . . . . .
C12 C 0.2993(4) 0.4376(9) 0.5612(3) 0.067(2) Uani 1 1 d . . . . .
C13 C 0.3428(4) 0.5248(8) 0.5397(3) 0.0639(19) Uani 1 1 d . . . . .
C14 C 0.3095(4) 0.6031(10) 0.4884(4) 0.080(2) Uani 1 1 d . . . . .
H14 H 0.2600 0.6014 0.4688 0.096 Uiso 1 1 calc R U . . .
C15 C 0.3513(5) 0.6841(9) 0.4669(4) 0.079(2) Uani 1 1 d . . . . .
H15 H 0.3296 0.7366 0.4326 0.094 Uiso 1 1 calc R U . . .
C16 C 0.4226(5) 0.6867(8) 0.4953(4) 0.069(2) Uani 1 1 d . . . . .
C17 C 0.4554(4) 0.6128(10) 0.5454(4) 0.085(3) Uani 1 1 d . . . . .
H17 H 0.5049 0.6165 0.5646 0.102 Uiso 1 1 calc R U . . .
C18 C 0.4163(5) 0.5323(9) 0.5683(4) 0.085(2) Uani 1 1 d . . . . .
H18 H 0.4393 0.4827 0.6032 0.101 Uiso 1 1 calc R U . . .
C19 C 0.3118(4) 0.1149(9) 0.6693(4) 0.0612(19) Uani 1 1 d . . . . .
C20 C 0.3992(4) 0.0241(8) 0.6322(3) 0.0644(19) Uani 1 1 d . . . . .
C21 C 0.4124(6) -0.1248(11) 0.6588(5) 0.116(4) Uani 1 1 d . . . . .
H21A H 0.4136 -0.1202 0.6976 0.174 Uiso 1 1 calc R U . . .
H21B H 0.4574 -0.1606 0.6604 0.174 Uiso 1 1 calc R U . . .
H21C H 0.3747 -0.1886 0.6355 0.174 Uiso 1 1 calc R U . . .
C22 C 0.3941(4) 0.0159(11) 0.5701(3) 0.084(3) Uani 1 1 d . . . . .
H22A H 0.3585 -0.0540 0.5487 0.125 Uiso 1 1 calc R U . . .
H22B H 0.4396 -0.0124 0.5704 0.125 Uiso 1 1 calc R U . . .
H22C H 0.3810 0.1091 0.5519 0.125 Uiso 1 1 calc R U . . .
C23 C 0.4544(4) 0.1336(10) 0.6661(4) 0.085(3) Uani 1 1 d . . . . .
H23A H 0.4397 0.2279 0.6495 0.128 Uiso 1 1 calc R U . . .
H23B H 0.4995 0.1093 0.6646 0.128 Uiso 1 1 calc R U . . .
H23C H 0.4593 0.1338 0.7060 0.128 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
Br1 C16 1.893(8) . ?
O1 C8 1.409(8) . ?
O1 H1 0.8200 . ?
O2 C19 1.218(9) . ?
O3 C19 1.340(8) . ?
O3 C20 1.479(8) . ?
N1 C19 1.355(10) . ?
N1 C10 1.456(9) . ?
N1 C7 1.459(8) . ?
C1 C2 1.376(12) . ?
C1 C6 1.386(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.362(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(10) . ?
C7 C8 1.560(11) . ?
C7 H7 0.9800 . ?
C8 C9 1.505(11) . ?
C8 H8 0.9800 . ?
C9 C10 1.522(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.475(10) . ?
C10 H10 0.9800 . ?
C11 C12 1.170(10) . ?
C12 C13 1.449(10) . ?
C13 C18 1.381(11) . ?
C13 C14 1.390(11) . ?
C14 C15 1.391(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.339(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.347(11) . ?
C17 C18 1.368(11) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C23 1.499(11) . ?
C20 C21 1.505(13) . ?
C20 C22 1.515(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C8 O1 H1 109.5 . . ?
C19 O3 C20 121.2(6) . . ?
C19 N1 C10 124.6(6) . . ?
C19 N1 C7 121.3(6) . . ?
C10 N1 C7 114.0(6) . . ?
C2 C1 C6 121.2(9) . . ?
C2 C1 H1A 119.4 . . ?
C6 C1 H1A 119.4 . . ?
C3 C2 C1 119.6(8) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.3(9) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(9) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 121.1(8) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.6(7) . . ?
C5 C6 C7 123.2(6) . . ?
C1 C6 C7 119.1(7) . . ?
N1 C7 C6 113.8(6) . . ?
N1 C7 C8 100.6(6) . . ?
C6 C7 C8 114.4(6) . . ?
N1 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
O1 C8 C9 110.3(6) . . ?
O1 C8 C7 114.5(6) . . ?
C9 C8 C7 102.4(6) . . ?
O1 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
C8 C9 C10 104.3(6) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N1 C10 C11 113.4(6) . . ?
N1 C10 C9 102.4(6) . . ?
C11 C10 C9 112.2(7) . . ?
N1 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
C12 C11 C10 177.0(8) . . ?
C11 C12 C13 177.0(8) . . ?
C18 C13 C14 118.9(7) . . ?
C18 C13 C12 122.1(7) . . ?
C14 C13 C12 119.0(7) . . ?
C13 C14 C15 119.1(7) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.3(8) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.1(8) . . ?
C15 C16 Br1 118.6(7) . . ?
C17 C16 Br1 120.3(6) . . ?
C16 C17 C18 120.6(8) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.0(8) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O2 C19 O3 126.1(7) . . ?
O2 C19 N1 123.4(6) . . ?
O3 C19 N1 110.4(7) . . ?
O3 C20 C23 108.3(6) . . ?
O3 C20 C21 112.5(7) . . ?
C23 C20 C21 113.9(8) . . ?
O3 C20 C22 101.9(6) . . ?
C23 C20 C22 110.1(7) . . ?
C21 C20 C22 109.5(8) . . ?
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 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 -0.3(15) . . . . ?
C1 C2 C3 C4 0.2(15) . . . . ?
C2 C3 C4 C5 0.3(15) . . . . ?
C3 C4 C5 C6 -0.8(13) . . . . ?
C4 C5 C6 C1 0.7(12) . . . . ?
C4 C5 C6 C7 -178.2(8) . . . . ?
C2 C1 C6 C5 -0.1(13) . . . . ?
C2 C1 C6 C7 178.8(8) . . . . ?
C19 N1 C7 C6 -75.8(8) . . . . ?
C10 N1 C7 C6 104.7(7) . . . . ?
C19 N1 C7 C8 161.4(6) . . . . ?
C10 N1 C7 C8 -18.0(7) . . . . ?
C5 C6 C7 N1 -20.0(10) . . . . ?
C1 C6 C7 N1 161.2(7) . . . . ?
C5 C6 C7 C8 94.9(8) . . . . ?
C1 C6 C7 C8 -83.9(9) . . . . ?
N1 C7 C8 O1 154.4(6) . . . . ?
C6 C7 C8 O1 32.0(9) . . . . ?
N1 C7 C8 C9 35.0(6) . . . . ?
C6 C7 C8 C9 -87.4(7) . . . . ?
O1 C8 C9 C10 -162.6(6) . . . . ?
C7 C8 C9 C10 -40.3(7) . . . . ?
C19 N1 C10 C11 -64.5(9) . . . . ?
C7 N1 C10 C11 114.9(7) . . . . ?
C19 N1 C10 C9 174.4(6) . . . . ?
C7 N1 C10 C9 -6.2(8) . . . . ?
C8 C9 C10 N1 29.1(7) . . . . ?
C8 C9 C10 C11 -92.9(8) . . . . ?
C18 C13 C14 C15 1.4(12) . . . . ?
C12 C13 C14 C15 -178.5(8) . . . . ?
C13 C14 C15 C16 -0.2(13) . . . . ?
C14 C15 C16 C17 -0.7(13) . . . . ?
C14 C15 C16 Br1 -179.0(6) . . . . ?
C15 C16 C17 C18 0.4(14) . . . . ?
Br1 C16 C17 C18 178.7(7) . . . . ?
C16 C17 C18 C13 0.8(14) . . . . ?
C14 C13 C18 C17 -1.7(13) . . . . ?
C12 C13 C18 C17 178.1(8) . . . . ?
C20 O3 C19 O2 -17.7(11) . . . . ?
C20 O3 C19 N1 160.7(6) . . . . ?
C10 N1 C19 O2 174.4(7) . . . . ?
C7 N1 C19 O2 -5.0(11) . . . . ?
C10 N1 C19 O3 -4.0(9) . . . . ?
C7 N1 C19 O3 176.6(6) . . . . ?
C19 O3 C20 C23 -58.9(9) . . . . ?
C19 O3 C20 C21 67.8(10) . . . . ?
C19 O3 C20 C22 -175.0(7) . . . . ?

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
C23 H23C O2 0.96 2.56 3.079(9) 114.4 .
C22 H22B Br1 0.96 2.94 3.513(8) 119.2 5_666
C21 H21A O2 0.96 2.48 3.051(12) 117.8 .
O1 H1 O2 0.82 2.02 2.822(8) 164.8 4_556
C23 H23C O2 0.96 2.56 3.079(9) 114.4 .
C22 H22B Br1 0.96 2.94 3.513(8) 119.2 5_666
C21 H21A O2 0.96 2.48 3.051(12) 117.8 .
O1 H1 O2 0.82 2.02 2.822(8) 164.8 4_556
C23 H23C O2 0.96 2.56 3.079(9) 114.4 .
C22 H22B Br1 0.96 2.94 3.513(8) 119.2 5_666
C21 H21A O2 0.96 2.48 3.051(12) 117.8 .
O1 H1 O2 0.82 2.02 2.822(8) 164.8 4_556
O1 H1 O2 0.82 2.02 2.822(8) 164.8 4_556
C21 H21A O2 0.96 2.48 3.051(12) 117.8 .
C22 H22B Br1 0.96 2.94 3.513(8) 119.2 5_666
C23 H23C O2 0.96 2.56 3.079(9) 114.4 .

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.084

_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_mo_ddz21108_0m
_database_code_depnum_ccdc_archive 'CCDC 2163796'
loop_
_audit_author_name
_audit_author_address
'Chang-Hong Liu'
;Fudan University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.3323(6)
_cell_length_b                   11.0667(5)
_cell_length_c                   14.5237(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.634(2)
_cell_angle_gamma                90
_cell_volume                     1681.15(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6568
_cell_measurement_theta_min      4.773
_cell_measurement_theta_max      53.431

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6557
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16753
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3294
_reflns_number_gt                2527
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       '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)+(0.0490P)²+0.3197P] 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     SHELXL
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O 0.89804(10) 0.21278(10) 0.50465(9) 0.0679(3) Uani 1 1 d . . . . .
O2 O 0.80876(9) 0.07846(9) 0.57643(7) 0.0584(3) Uani 1 1 d . . . . .
N1 N 0.69821(11) 0.14085(11) 0.42131(8) 0.0489(3) Uani 1 1 d . . . . .
C1 C 0.67376(16) 0.22281(15) 0.33694(11) 0.0606(4) Uani 1 1 d . . . . .
H1A H 0.7537 0.2577 0.3401 0.073 Uiso 1 1 calc R U . . .
H1B H 0.6186 0.2881 0.3405 0.073 Uiso 1 1 calc R U . . .
C2 C 0.61090(18) 0.15572(18) 0.23944(12) 0.0724(5) Uani 1 1 d . . . . .
H2A H 0.6708 0.0979 0.2319 0.087 Uiso 1 1 calc R U . . .
H2B H 0.5883 0.2126 0.1845 0.087 Uiso 1 1 calc R U . . .
C3 C 0.49180(17) 0.09001(18) 0.23559(12) 0.0733(5) Uani 1 1 d . . . . .
H3A H 0.4570 0.0430 0.1747 0.088 Uiso 1 1 calc R U . . .
H3B H 0.4277 0.1484 0.2352 0.088 Uiso 1 1 calc R U . . .
C4 C 0.52287(16) 0.00703(15) 0.32495(12) 0.0639(4) Uani 1 1 d . . . . .
H4A H 0.5795 -0.0567 0.3210 0.077 Uiso 1 1 calc R U . . .
H4B H 0.4448 -0.0303 0.3236 0.077 Uiso 1 1 calc R U . . .
C5 C 0.58650(13) 0.07573(13) 0.42296(11) 0.0487(4) Uani 1 1 d . . . . .
H5 H 0.6156 0.0170 0.4776 0.058 Uiso 1 1 calc R U . . .
C6 C 0.49624(14) 0.15956(14) 0.44058(11) 0.0520(4) Uani 1 1 d . . . . .
C7 C 0.42145(14) 0.22805(14) 0.45184(11) 0.0536(4) Uani 1 1 d . . . . .
C8 C 0.33418(13) 0.31269(14) 0.46637(10) 0.0498(4) Uani 1 1 d . . . . .
C9 C 0.34096(16) 0.43443(15) 0.44585(12) 0.0601(4) Uani 1 1 d . . . . .
H9 H 0.4004 0.4604 0.4204 0.072 Uiso 1 1 calc R U . . .
C10 C 0.26103(17) 0.51694(16) 0.46270(13) 0.0678(5) Uani 1 1 d . . . . .
H10 H 0.2670 0.5982 0.4489 0.081 Uiso 1 1 calc R U . . .
C11 C 0.17273(15) 0.48044(17) 0.49965(13) 0.0674(5) Uani 1 1 d . . . . .
H11 H 0.1195 0.5368 0.5118 0.081 Uiso 1 1 calc R U . . .
C12 C 0.16293(15) 0.36020(18) 0.51876(14) 0.0701(5) Uani 1 1 d . . . . .
H12 H 0.1018 0.3351 0.5428 0.084 Uiso 1 1 calc R U . . .
C13 C 0.24285(14) 0.27639(15) 0.50260(12) 0.0608(4) Uani 1 1 d . . . . .
H13 H 0.2356 0.1952 0.5160 0.073 Uiso 1 1 calc R U . . .
C14 C 0.80974(13) 0.14990(12) 0.50192(11) 0.0473(3) Uani 1 1 d . . . . .
C15 C 0.92003(14) 0.06939(14) 0.67120(11) 0.0571(4) Uani 1 1 d . . . . .
C16 C 0.9515(2) 0.19120(18) 0.72027(15) 0.0972(7) Uani 1 1 d . . . . .
H16A H 0.9846 0.2425 0.6825 0.146 Uiso 1 1 calc R U . . .
H16B H 1.0144 0.1822 0.7868 0.146 Uiso 1 1 calc R U . . .
H16C H 0.8755 0.2267 0.7228 0.146 Uiso 1 1 calc R U . . .
C17 C 0.87140(19) -0.01401(19) 0.73160(13) 0.0828(6) Uani 1 1 d . . . . .
H17A H 0.8010 0.0236 0.7417 0.124 Uiso 1 1 calc R U . . .
H17B H 0.9389 -0.0297 0.7950 0.124 Uiso 1 1 calc R U . . .
H17C H 0.8436 -0.0887 0.6963 0.124 Uiso 1 1 calc R U . . .
C18 C 1.02994(19) 0.0131(2) 0.65314(17) 0.0989(7) Uani 1 1 d . . . . .
H18A H 1.0021 -0.0605 0.6162 0.148 Uiso 1 1 calc R U . . .
H18B H 1.0980 -0.0042 0.7159 0.148 Uiso 1 1 calc R U . . .
H18C H 1.0599 0.0681 0.6158 0.148 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
O1 C14 1.2069(16) . ?
O2 C14 1.3436(17) . ?
O2 C15 1.4692(16) . ?
N1 C14 1.3561(18) . ?
N1 C1 1.4627(18) . ?
N1 C5 1.4649(17) . ?
C1 C2 1.512(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.528(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.474(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.194(2) . ?
C7 C8 1.435(2) . ?
C8 C9 1.388(2) . ?
C8 C13 1.389(2) . ?
C9 C10 1.373(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C16 1.502(2) . ?
C15 C18 1.503(2) . ?
C15 C17 1.516(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C14 O2 C15 121.64(11) . . ?
C14 N1 C1 119.38(12) . . ?
C14 N1 C5 123.12(11) . . ?
C1 N1 C5 115.62(11) . . ?
N1 C1 C2 110.43(14) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 111.22(14) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 110.43(14) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 111.52(14) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C6 110.79(11) . . ?
N1 C5 C4 109.30(12) . . ?
C6 C5 C4 111.39(12) . . ?
N1 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C7 C6 C5 178.03(16) . . ?
C6 C7 C8 178.50(16) . . ?
C9 C8 C13 118.23(14) . . ?
C9 C8 C7 120.23(14) . . ?
C13 C8 C7 121.53(14) . . ?
C10 C9 C8 120.82(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.44(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.65(16) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.56(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.28(16) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
O1 C14 O2 125.20(13) . . ?
O1 C14 N1 123.81(13) . . ?
O2 C14 N1 110.98(12) . . ?
O2 C15 C16 110.16(14) . . ?
O2 C15 C18 109.56(14) . . ?
C16 C15 C18 113.16(18) . . ?
O2 C15 C17 102.22(12) . . ?
C16 C15 C17 110.16(16) . . ?
C18 C15 C17 111.03(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C14 N1 C1 C2 139.40(14) . . . . ?
C5 N1 C1 C2 -55.74(17) . . . . ?
N1 C1 C2 C3 53.94(19) . . . . ?
C1 C2 C3 C4 -55.0(2) . . . . ?
C2 C3 C4 C5 55.36(18) . . . . ?
C14 N1 C5 C6 96.45(15) . . . . ?
C1 N1 C5 C6 -67.79(16) . . . . ?
C14 N1 C5 C4 -140.43(13) . . . . ?
C1 N1 C5 C4 55.32(16) . . . . ?
C3 C4 C5 N1 -54.03(17) . . . . ?
C3 C4 C5 C6 68.73(17) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C7 C8 C9 C10 -177.72(14) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 -0.9(2) . . . . ?
C7 C8 C13 C12 177.97(14) . . . . ?
C15 O2 C14 O1 -0.6(2) . . . . ?
C15 O2 C14 N1 178.30(12) . . . . ?
C1 N1 C14 O1 -8.8(2) . . . . ?
C5 N1 C14 O1 -172.47(14) . . . . ?
C1 N1 C14 O2 172.28(12) . . . . ?
C5 N1 C14 O2 8.60(18) . . . . ?
C14 O2 C15 C16 59.9(2) . . . . ?
C14 O2 C15 C18 -65.20(19) . . . . ?
C14 O2 C15 C17 176.99(14) . . . . ?

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
C18 H18C O1 0.96 2.50 3.047(2) 116.0 .
C16 H16A O1 0.96 2.41 2.961(2) 116.4 .
C18 H18C O1 0.96 2.50 3.047(2) 116.0 .
C16 H16A O1 0.96 2.41 2.961(2) 116.4 .
C16 H16A O1 0.96 2.41 2.961(2) 116.4 .
C18 H18C O1 0.96 2.50 3.047(2) 116.0 .

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4



