# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_cd214151
_database_code_depnum_ccdc_archive 'CCDC 1957048'
loop_
_audit_author_name
_audit_author_address
'Jinxing Ye'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Br N O3'
_chemical_formula_weight         352.22

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      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                   8.4827(10)
_cell_length_b                   10.4094(12)
_cell_length_c                   17.8022(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1571.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2731
_cell_measurement_theta_min      4.533
_cell_measurement_theta_max      '? 50.806'

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    2.624
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5346
_exptl_absorpt_correction_T_max  0.7457
_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            9482
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3090
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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)+(0.0285P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0097(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.016(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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 0.80636(6) 0.72399(6) 1.08358(2) 0.0720(2) Uani 1 1 d . . . . .
N1 N 0.5285(4) 0.9494(4) 0.7465(2) 0.0537(9) Uani 1 1 d . . . . .
O1 O 0.9228(5) 0.6209(3) 0.44178(17) 0.0767(11) Uani 1 1 d . . . . .
O2 O 0.5879(5) 1.0536(4) 0.7530(3) 0.0952(13) Uani 1 1 d . . . . .
O3 O 0.3934(4) 0.9286(5) 0.7621(2) 0.0952(13) Uani 1 1 d . . . . .
C1 C 0.6236(5) 0.8423(5) 0.7149(2) 0.0479(10) Uani 1 1 d . . . . .
H1A H 0.6257 0.8492 0.6606 0.058 Uiso 1 1 calc R U . . .
H1B H 0.5746 0.7611 0.7279 0.058 Uiso 1 1 calc R U . . .
C2 C 0.7911(4) 0.8446(4) 0.74485(18) 0.0383(8) Uani 1 1 d . . . . .
H2 H 0.8322 0.9319 0.7382 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8967(5) 0.7524(4) 0.6991(2) 0.0457(10) Uani 1 1 d . . . . .
H3 H 0.8548 0.6652 0.7047 0.055 Uiso 1 1 calc R U . . .
C4 C 1.0654(5) 0.7541(6) 0.7303(3) 0.0725(15) Uani 1 1 d . . . . .
H4A H 1.1301 0.6965 0.7017 0.109 Uiso 1 1 calc R U . . .
H4B H 1.0641 0.7274 0.7819 0.109 Uiso 1 1 calc R U . . .
H4C H 1.1073 0.8396 0.7269 0.109 Uiso 1 1 calc R U . . .
C5 C 0.9006(4) 0.7844(4) 0.6164(2) 0.0431(9) Uani 1 1 d . . . . .
C6 C 0.9245(6) 0.9189(4) 0.5916(3) 0.0637(13) Uani 1 1 d . . . . .
H6A H 0.8267 0.9654 0.5992 0.076 Uiso 1 1 calc R U . . .
H6B H 1.0033 0.9579 0.6239 0.076 Uiso 1 1 calc R U . . .
C7 C 0.9737(7) 0.9367(5) 0.5135(3) 0.0761(15) Uani 1 1 d D . . . .
H7A H 1.0877 0.9300 0.5112 0.091 Uiso 1 1 calc R U . . .
H7B H 0.9456 1.0231 0.4981 0.091 Uiso 1 1 calc R U . . .
C8 C 0.9057(8) 0.8454(5) 0.4592(3) 0.0751(15) Uani 1 1 d D . . . .
H8A H 0.7976 0.8702 0.4487 0.090 Uiso 1 1 calc R U . . .
H8B H 0.9643 0.8508 0.4125 0.090 Uiso 1 1 calc R U . . .
C9 C 0.9076(5) 0.7115(4) 0.4858(2) 0.0514(10) Uani 1 1 d . . . . .
C10 C 0.8898(5) 0.6906(4) 0.5654(2) 0.0431(10) Uani 1 1 d . . . . .
H10 H 0.8699 0.6075 0.5822 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7951(4) 0.8141(4) 0.82792(18) 0.0378(8) Uani 1 1 d . . . . .
C12 C 0.8610(4) 0.8983(4) 0.8780(2) 0.0454(10) Uani 1 1 d . . . . .
H12 H 0.9030 0.9751 0.8604 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8666(5) 0.8720(5) 0.9539(2) 0.0514(11) Uani 1 1 d . . . . .
H13 H 0.9125 0.9301 0.9870 0.062 Uiso 1 1 calc R U . . .
C14 C 0.8041(5) 0.7599(4) 0.9796(2) 0.0466(9) Uani 1 1 d . . . . .
C15 C 0.7378(5) 0.6724(5) 0.9311(2) 0.0516(11) Uani 1 1 d . . . . .
H15 H 0.6955 0.5959 0.9491 0.062 Uiso 1 1 calc R U . . .
C16 C 0.7351(5) 0.6999(4) 0.8557(2) 0.0494(11) Uani 1 1 d . . . . .
H16 H 0.6920 0.6405 0.8225 0.059 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 C14 1.889(4) . ?
N1 O3 1.199(5) . ?
N1 O2 1.202(5) . ?
N1 C1 1.486(6) . ?
O1 C9 1.232(5) . ?
C1 C2 1.518(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C11 1.513(5) . ?
C2 C3 1.546(5) . ?
C2 H2 0.9800 . ?
C3 C5 1.509(5) . ?
C3 C4 1.535(6) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.337(6) . ?
C5 C6 1.482(6) . ?
C6 C7 1.463(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.473(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.473(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.443(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(5) . ?
C11 C16 1.384(6) . ?
C12 C13 1.379(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(6) . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 H16 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
O3 N1 O2 122.7(5) . . ?
O3 N1 C1 118.1(5) . . ?
O2 N1 C1 119.1(4) . . ?
N1 C1 C2 111.3(3) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C11 C2 C1 111.1(3) . . ?
C11 C2 C3 111.8(3) . . ?
C1 C2 C3 110.3(3) . . ?
C11 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C5 C3 C4 109.3(3) . . ?
C5 C3 C2 112.9(3) . . ?
C4 C3 C2 110.0(3) . . ?
C5 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.9(4) . . ?
C10 C5 C3 119.9(4) . . ?
C6 C5 C3 120.2(4) . . ?
C7 C6 C5 116.2(4) . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 C8 115.5(4) . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 113.3(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C10 121.4(4) . . ?
O1 C9 C8 121.4(4) . . ?
C10 C9 C8 117.2(4) . . ?
C5 C10 C9 123.4(4) . . ?
C5 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C12 C11 C16 117.9(3) . . ?
C12 C11 C2 120.7(4) . . ?
C16 C11 C2 121.4(3) . . ?
C11 C12 C13 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.1(4) . . ?
C13 C14 Br1 119.7(3) . . ?
C15 C14 Br1 119.2(3) . . ?
C16 C15 C14 118.8(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 121.5(4) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 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
O3 N1 C1 C2 -141.7(4) . . . . ?
O2 N1 C1 C2 40.6(6) . . . . ?
N1 C1 C2 C11 67.6(5) . . . . ?
N1 C1 C2 C3 -167.7(3) . . . . ?
C11 C2 C3 C5 -177.4(3) . . . . ?
C1 C2 C3 C5 58.3(5) . . . . ?
C11 C2 C3 C4 -55.1(5) . . . . ?
C1 C2 C3 C4 -179.3(4) . . . . ?
C4 C3 C5 C10 100.8(5) . . . . ?
C2 C3 C5 C10 -136.4(4) . . . . ?
C4 C3 C5 C6 -76.1(5) . . . . ?
C2 C3 C5 C6 46.7(5) . . . . ?
C10 C5 C6 C7 -14.7(7) . . . . ?
C3 C5 C6 C7 162.2(4) . . . . ?
C5 C6 C7 C8 35.8(7) . . . . ?
C6 C7 C8 C9 -44.5(7) . . . . ?
C7 C8 C9 O1 -147.8(5) . . . . ?
C7 C8 C9 C10 32.6(7) . . . . ?
C6 C5 C10 C9 3.0(6) . . . . ?
C3 C5 C10 C9 -173.9(4) . . . . ?
O1 C9 C10 C5 167.9(4) . . . . ?
C8 C9 C10 C5 -12.6(6) . . . . ?
C1 C2 C11 C12 -123.0(4) . . . . ?
C3 C2 C11 C12 113.2(4) . . . . ?
C1 C2 C11 C16 58.1(5) . . . . ?
C3 C2 C11 C16 -65.7(5) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C2 C11 C12 C13 -179.6(4) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C12 C13 C14 Br1 -178.6(3) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
Br1 C14 C15 C16 179.3(3) . . . . ?
C14 C15 C16 C11 -1.1(6) . . . . ?
C12 C11 C16 C15 1.5(6) . . . . ?
C2 C11 C16 C15 -179.6(4) . . . . ?

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
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665
C1 H1A O1 0.97 2.53 3.291(5) 135.7 4_466
C1 H1B O2 0.97 2.58 3.546(6) 171.2 3_646
C15 H15 O1 0.93 2.47 3.349(6) 156.8 2_665

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054

_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_cd214200
_database_code_depnum_ccdc_archive 'CCDC 1957050'
loop_
_audit_author_name
_audit_author_address
'Jinxing Ye'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-06-07 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 H22 Br N O3'
_chemical_formula_weight         380.27

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      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                   8.9889(10)
_cell_length_b                   10.1859(11)
_cell_length_c                   20.073(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1837.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2533
_cell_measurement_theta_min      4.484
_cell_measurement_theta_max      40.124

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    2.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_T_max  0.7457
_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            11129
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3617
_reflns_number_gt                2642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       '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)+(0.0414P)²+0.0758P] 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 955 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.005(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3617
_refine_ls_number_parameters     242
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.035
_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 0.89735(7) 0.11596(5) 0.11144(3) 0.0884(3) Uani 1 1 d . . . . .
O1 O 1.0516(4) 0.7887(5) 0.07194(18) 0.0856(12) Uani 1 1 d . . . . .
C1 C 0.8000(5) 0.7428(4) 0.0876(2) 0.0486(11) Uani 1 1 d . . . . .
H1 H 0.7837 0.7370 0.0420 0.058 Uiso 1 1 calc R U . . .
C2 C 0.9511(5) 0.7662(5) 0.1107(2) 0.0563(11) Uani 1 1 d . . . . .
C3 C 0.9764(6) 0.7672(6) 0.1843(2) 0.0711(14) Uani 1 1 d . . . . .
H3A H 0.9769 0.8573 0.1998 0.085 Uiso 1 1 calc R U . . .
H3B H 1.0735 0.7299 0.1936 0.085 Uiso 1 1 calc R U . . .
C4 C 0.8601(6) 0.6912(6) 0.2224(2) 0.0745(16) Uani 1 1 d . . . . .
H4A H 0.8714 0.5981 0.2135 0.089 Uiso 1 1 calc R U . . .
H4B H 0.8737 0.7051 0.2698 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7064(6) 0.7346(6) 0.2024(2) 0.0628(13) Uani 1 1 d . . . . .
H5A H 0.6902 0.8237 0.2178 0.075 Uiso 1 1 calc R U . . .
H5B H 0.6335 0.6786 0.2240 0.075 Uiso 1 1 calc R U . . .
C6 C 0.6837(5) 0.7293(4) 0.12818(18) 0.0457(10) Uani 1 1 d . . . . .
C7 C 0.5276(5) 0.7145(4) 0.1020(2) 0.0476(10) Uani 1 1 d . . . . .
H7 H 0.5337 0.7131 0.0533 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4309(5) 0.8310(4) 0.1213(2) 0.0571(11) Uani 1 1 d . . . . .
H8A H 0.4278 0.8369 0.1695 0.069 Uiso 1 1 calc R U . . .
H8B H 0.3303 0.8148 0.1059 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4829(7) 0.9628(5) 0.0935(3) 0.0837(17) Uani 1 1 d . . . . .
H9A H 0.5829 0.9803 0.1094 0.100 Uiso 1 1 calc R U . . .
H9B H 0.4866 0.9575 0.0453 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3837(9) 1.0745(6) 0.1132(3) 0.102(2) Uani 1 1 d . . . . .
H10A H 0.2863 1.0612 0.0946 0.152 Uiso 1 1 calc R U . . .
H10B H 0.4243 1.1553 0.0966 0.152 Uiso 1 1 calc R U . . .
H10C H 0.3768 1.0785 0.1608 0.152 Uiso 1 1 calc R U . . .
C11 C 0.4574(5) 0.5815(4) 0.1243(2) 0.0503(11) Uani 1 1 d . . . . .
H11 H 0.4266 0.5911 0.1709 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5649(5) 0.4669(4) 0.1208(2) 0.0490(10) Uani 1 1 d . . . . .
C13 C 0.5995(6) 0.3969(5) 0.1773(2) 0.0637(12) Uani 1 1 d . . . . .
H13 H 0.5564 0.4198 0.2177 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6984(7) 0.2923(5) 0.1745(3) 0.0683(14) Uani 1 1 d . . . . .
H14 H 0.7203 0.2447 0.2128 0.082 Uiso 1 1 calc R U . . .
C15 C 0.7630(5) 0.2596(4) 0.1156(3) 0.0608(12) Uani 1 1 d . . . . .
C16 C 0.7290(7) 0.3272(5) 0.0589(2) 0.0710(15) Uani 1 1 d . . . . .
H16 H 0.7721 0.3036 0.0185 0.085 Uiso 1 1 calc R U . . .
C17 C 0.6306(7) 0.4306(5) 0.0619(2) 0.0630(14) Uani 1 1 d . . . . .
H17 H 0.6082 0.4769 0.0232 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3183(6) 0.5558(5) 0.0833(3) 0.0638(13) Uani 1 1 d D . . . .
H18A H 0.2659 0.6382 0.0772 0.077 Uiso 0.5 1 calc R U P A 1
H18B H 0.3481 0.5250 0.0396 0.077 Uiso 0.5 1 calc R U P A 1
H18C H 0.342(12) 0.527(10) 0.033(5) 0.077 Uiso 0.5 1 d . U P B 2
H18D H 0.235(13) 0.642(10) 0.091(4) 0.077 Uiso 0.5 1 d . U P C 2
N1' N 0.244(5) 0.451(3) 0.1228(16) 0.082(4) Uani 0.3 1 d D U P D 2
O3' O 0.205(2) 0.3523(16) 0.0917(11) 0.142(7) Uani 0.5 1 d D U P D 2
O2' O 0.179(3) 0.483(3) 0.1734(13) 0.128(9) Uani 0.5 1 d D U P D 2
N1 N 0.2126(16) 0.4576(13) 0.1130(7) 0.081(4) Uani 0.7 1 d D U P D 1
O3 O 0.146(3) 0.393(2) 0.0718(12) 0.169(9) Uani 0.5 1 d D U P D 1
O2 O 0.208(3) 0.447(3) 0.1726(11) 0.120(8) Uani 0.5 1 d D U P D 1


_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 C15 1.899(4) . ?
O1 C2 1.214(6) . ?
C1 C6 1.332(6) . ?
C1 C2 1.455(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.494(7) . ?
C3 C4 1.510(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.505(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.506(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.506(6) . ?
C7 C8 1.521(6) . ?
C7 C11 1.560(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.527(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.498(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.517(6) . ?
C11 C18 1.520(7) . ?
C11 H11 0.9800 . ?
C12 C17 1.371(7) . ?
C12 C13 1.376(6) . ?
C13 C14 1.388(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(7) . ?
C16 C17 1.377(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1' 1.49(2) . ?
C18 N1 1.503(12) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 1.07(10) . ?
C18 H18D 1.16(11) . ?
N1' O2' 1.22(2) . ?
N1' O3' 1.24(2) . ?
N1 O2 1.20(2) . ?
N1 O3 1.217(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.7(4) . . ?
C6 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
O1 C2 C1 121.4(4) . . ?
O1 C2 C3 121.3(4) . . ?
C1 C2 C3 117.3(4) . . ?
C2 C3 C4 113.1(4) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 110.5(4) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 112.2(4) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 C5 119.7(4) . . ?
C1 C6 C7 121.9(4) . . ?
C5 C6 C7 118.4(4) . . ?
C6 C7 C8 111.4(4) . . ?
C6 C7 C11 111.3(3) . . ?
C8 C7 C11 111.9(4) . . ?
C6 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C11 C7 H7 107.3 . . ?
C7 C8 C9 114.7(4) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 112.9(5) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C18 111.4(4) . . ?
C12 C11 C7 113.4(4) . . ?
C18 C11 C7 109.0(4) . . ?
C12 C11 H11 107.6 . . ?
C18 C11 H11 107.6 . . ?
C7 C11 H11 107.6 . . ?
C17 C12 C13 118.2(4) . . ?
C17 C12 C11 121.5(4) . . ?
C13 C12 C11 120.3(4) . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 Br1 119.9(4) . . ?
C16 C15 Br1 119.7(4) . . ?
C15 C16 C17 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 121.4(4) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N1' C18 C11 101.7(19) . . ?
N1 C18 C11 114.8(7) . . ?
N1 C18 H18A 108.6 . . ?
C11 C18 H18A 108.6 . . ?
N1 C18 H18B 108.6 . . ?
C11 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
N1' C18 H18C 114(6) . . ?
C11 C18 H18C 113(6) . . ?
N1' C18 H18D 100(5) . . ?
C11 C18 H18D 109(5) . . ?
H18C C18 H18D 118(7) . . ?
O2' N1' O3' 120(3) . . ?
O2' N1' C18 118(2) . . ?
O3' N1' C18 116(2) . . ?
O2 N1 O3 128(2) . . ?
O2 N1 C18 118.3(16) . . ?
O3 N1 C18 113.8(16) . . ?

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 O1 -173.8(5) . . . . ?
C6 C1 C2 C3 3.6(7) . . . . ?
O1 C2 C3 C4 -158.9(5) . . . . ?
C1 C2 C3 C4 23.7(7) . . . . ?
C2 C3 C4 C5 -51.3(6) . . . . ?
C3 C4 C5 C6 53.0(6) . . . . ?
C2 C1 C6 C5 -1.6(7) . . . . ?
C2 C1 C6 C7 175.7(4) . . . . ?
C4 C5 C6 C1 -27.5(7) . . . . ?
C4 C5 C6 C7 155.2(4) . . . . ?
C1 C6 C7 C8 -114.7(4) . . . . ?
C5 C6 C7 C8 62.6(5) . . . . ?
C1 C6 C7 C11 119.6(5) . . . . ?
C5 C6 C7 C11 -63.1(5) . . . . ?
C6 C7 C8 C9 61.9(5) . . . . ?
C11 C7 C8 C9 -172.8(4) . . . . ?
C7 C8 C9 C10 179.4(5) . . . . ?
C6 C7 C11 C12 -41.1(5) . . . . ?
C8 C7 C11 C12 -166.6(3) . . . . ?
C6 C7 C11 C18 -165.9(4) . . . . ?
C8 C7 C11 C18 68.6(5) . . . . ?
C18 C11 C12 C17 63.9(6) . . . . ?
C7 C11 C12 C17 -59.6(6) . . . . ?
C18 C11 C12 C13 -116.6(5) . . . . ?
C7 C11 C12 C13 119.9(5) . . . . ?
C17 C12 C13 C14 -0.1(8) . . . . ?
C11 C12 C13 C14 -179.6(5) . . . . ?
C12 C13 C14 C15 0.8(8) . . . . ?
C13 C14 C15 C16 -1.3(8) . . . . ?
C13 C14 C15 Br1 -179.6(4) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
Br1 C15 C16 C17 179.5(4) . . . . ?
C13 C12 C17 C16 -0.1(8) . . . . ?
C11 C12 C17 C16 179.5(5) . . . . ?
C15 C16 C17 C12 -0.4(9) . . . . ?
C12 C11 C18 N1' 69.9(15) . . . . ?
C7 C11 C18 N1' -164.2(15) . . . . ?
C12 C11 C18 N1 73.2(8) . . . . ?
C7 C11 C18 N1 -160.9(7) . . . . ?
N1 C18 N1' O2' -90(10) . . . . ?
C11 C18 N1' O2' 77(4) . . . . ?
N1 C18 N1' O3' 64(6) . . . . ?
C11 C18 N1' O3' -129(4) . . . . ?
N1' C18 N1 O2 43(7) . . . . ?
C11 C18 N1 O2 29.3(19) . . . . ?
N1' C18 N1 O3 -133(8) . . . . ?
C11 C18 N1 O3 -147.2(16) . . . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.051

_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_d8v18035_0m
_database_code_depnum_ccdc_archive 'CCDC 1957051'
loop_
_audit_author_name
_audit_author_address
'Jinxing Ye'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-06-07 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 H22 Br N O3'
_chemical_formula_weight         380.27

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                   10.5022(3)
_cell_length_b                   7.3534(2)
_cell_length_c                   11.4093(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.5450(10)
_cell_angle_gamma                90
_cell_volume                     863.28(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      4.814
_cell_measurement_theta_max      54.973

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.395
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4350
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            14120
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3291
_reflns_number_gt                3178
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.953

_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)+(0.0116P)²+0.2698P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1380 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.032(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0568
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.16617(2) 0.72273(6) -0.05519(2) 0.03756(14) Uani 1 1 d . . . . .
N1 N 0.6122(2) 0.2619(3) 0.3717(2) 0.0268(7) Uani 1 1 d . . . . .
O1 O 1.14174(18) 0.7173(6) 0.40800(19) 0.0409(5) Uani 1 1 d . . . . .
O2 O 0.6424(3) 0.2095(5) 0.2797(2) 0.0489(6) Uani 1 1 d . . . . .
O3 O 0.5564(2) 0.1673(3) 0.4332(2) 0.0357(6) Uani 1 1 d . . . . .
C1 C 0.8123(3) 0.8374(5) 0.2698(3) 0.0309(7) Uani 1 1 d . . . . .
H1A H 0.8323 0.9674 0.2873 0.037 Uiso 1 1 calc R U . . .
H1B H 0.7559 0.8294 0.1892 0.037 Uiso 1 1 calc R U . . .
C2 C 0.9387(3) 0.7339(9) 0.2702(2) 0.0353(7) Uani 1 1 d . . . . .
H2A H 0.9180 0.6087 0.2405 0.042 Uiso 1 1 calc R U . . .
H2B H 0.9872 0.7946 0.2152 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0228(2) 0.7258(7) 0.3936(2) 0.0294(6) Uani 1 1 d . . . . .
C4 C 0.9579(2) 0.7304(7) 0.4954(2) 0.0288(6) Uani 1 1 d . . . . .
H4 H 1.0097 0.7184 0.5734 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8284(3) 0.7506(5) 0.4845(2) 0.0250(7) Uani 1 1 d . . . . .
C6 C 0.7396(3) 0.7611(4) 0.3622(3) 0.0234(7) Uani 1 1 d . . . . .
H6 H 0.6686 0.8490 0.3687 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6732(3) 0.5769(4) 0.3162(3) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.7343 0.5111 0.2741 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6468(3) 0.4521(4) 0.4155(3) 0.0237(6) Uani 1 1 d . . . . .
H8A H 0.7250 0.4478 0.4804 0.028 Uiso 1 1 calc R U . . .
H8B H 0.5747 0.5031 0.4492 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5496(3) 0.6133(4) 0.2243(3) 0.0208(6) Uani 1 1 d . . . . .
C10 C 0.4441(3) 0.7003(5) 0.2574(2) 0.0255(7) Uani 1 1 d . . . . .
H10 H 0.4503 0.7375 0.3381 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3306(2) 0.7337(7) 0.1748(2) 0.0280(6) Uani 1 1 d . . . . .
H11 H 0.2590 0.7916 0.1985 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3234(3) 0.6811(4) 0.0573(2) 0.0258(8) Uani 1 1 d . . . . .
C13 C 0.4258(3) 0.5958(4) 0.0205(3) 0.0283(7) Uani 1 1 d . . . . .
H13 H 0.4197 0.5611 -0.0606 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5385(3) 0.5617(4) 0.1058(3) 0.0253(6) Uani 1 1 d . . . . .
H14 H 0.6093 0.5018 0.0820 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7624(3) 0.7795(4) 0.5882(3) 0.0298(7) Uani 1 1 d . . . . .
H15A H 0.6811 0.7074 0.5727 0.036 Uiso 1 1 calc R U . . .
H15B H 0.7370 0.9091 0.5880 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8348(3) 0.7336(8) 0.7131(2) 0.0345(6) Uani 1 1 d . . . . .
H16A H 0.9060 0.8222 0.7383 0.041 Uiso 1 1 calc R U . . .
H16B H 0.8738 0.6110 0.7132 0.041 Uiso 1 1 calc R U . . .
C17 C 0.7423(3) 0.7381(8) 0.8017(3) 0.0389(8) Uani 1 1 d . . . . .
H17A H 0.6945 0.8550 0.7928 0.047 Uiso 1 1 calc R U . . .
H17B H 0.6778 0.6391 0.7816 0.047 Uiso 1 1 calc R U . . .
C18 C 0.8116(3) 0.7172(11) 0.9298(3) 0.0486(8) Uani 1 1 d . . . . .
H18A H 0.8593 0.6018 0.9394 0.073 Uiso 1 1 calc R U . . .
H18B H 0.7480 0.7180 0.9820 0.073 Uiso 1 1 calc R U . . .
H18C H 0.8727 0.8181 0.9516 0.073 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 C12 1.903(3) . ?
N1 O2 1.219(3) . ?
N1 O3 1.219(3) . ?
N1 C8 1.505(4) . ?
O1 C3 1.228(3) . ?
C1 C6 1.528(4) . ?
C1 C2 1.530(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.460(4) . ?
C4 C5 1.349(4) . ?
C4 H4 0.9500 . ?
C5 C15 1.501(4) . ?
C5 C6 1.517(4) . ?
C6 C7 1.565(4) . ?
C6 H6 1.0000 . ?
C7 C9 1.520(4) . ?
C7 C8 1.525(4) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.386(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.513(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.536(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.505(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
O2 N1 O3 123.6(3) . . ?
O2 N1 C8 119.5(3) . . ?
O3 N1 C8 116.8(2) . . ?
C6 C1 C2 111.6(3) . . ?
C6 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C6 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 111.6(3) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 121.3(2) . . ?
O1 C3 C2 121.2(2) . . ?
C4 C3 C2 117.6(2) . . ?
C5 C4 C3 123.5(2) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C15 124.0(2) . . ?
C4 C5 C6 120.9(2) . . ?
C15 C5 C6 114.9(2) . . ?
C5 C6 C1 110.7(2) . . ?
C5 C6 C7 114.5(2) . . ?
C1 C6 C7 109.7(2) . . ?
C5 C6 H6 107.2 . . ?
C1 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C9 C7 C8 111.2(2) . . ?
C9 C7 C6 109.9(2) . . ?
C8 C7 C6 114.0(2) . . ?
C9 C7 H7 107.1 . . ?
C8 C7 H7 107.1 . . ?
C6 C7 H7 107.1 . . ?
N1 C8 C7 112.3(2) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.2(3) . . ?
C14 C9 C7 121.3(3) . . ?
C10 C9 C7 120.5(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 Br1 119.4(2) . . ?
C11 C12 Br1 118.7(2) . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C9 C14 C13 121.7(3) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C5 C15 C16 119.1(3) . . ?
C5 C15 H15A 107.5 . . ?
C16 C15 H15A 107.5 . . ?
C5 C15 H15B 107.5 . . ?
C16 C15 H15B 107.5 . . ?
H15A C15 H15B 107.0 . . ?
C15 C16 C17 110.5(3) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 113.0(3) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 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
C6 C1 C2 C3 -53.4(5) . . . . ?
C1 C2 C3 O1 -150.7(5) . . . . ?
C1 C2 C3 C4 28.7(6) . . . . ?
O1 C3 C4 C5 175.9(5) . . . . ?
C2 C3 C4 C5 -3.5(7) . . . . ?
C3 C4 C5 C15 -171.8(4) . . . . ?
C3 C4 C5 C6 3.0(7) . . . . ?
C4 C5 C6 C1 -27.6(5) . . . . ?
C15 C5 C6 C1 147.7(3) . . . . ?
C4 C5 C6 C7 97.0(4) . . . . ?
C15 C5 C6 C7 -87.7(3) . . . . ?
C2 C1 C6 C5 52.3(4) . . . . ?
C2 C1 C6 C7 -75.1(3) . . . . ?
C5 C6 C7 C9 156.6(2) . . . . ?
C1 C6 C7 C9 -78.2(3) . . . . ?
C5 C6 C7 C8 31.0(3) . . . . ?
C1 C6 C7 C8 156.2(2) . . . . ?
O2 N1 C8 C7 20.5(4) . . . . ?
O3 N1 C8 C7 -160.8(2) . . . . ?
C9 C7 C8 N1 68.2(3) . . . . ?
C6 C7 C8 N1 -166.8(2) . . . . ?
C8 C7 C9 C14 -118.4(3) . . . . ?
C6 C7 C9 C14 114.4(3) . . . . ?
C8 C7 C9 C10 61.7(4) . . . . ?
C6 C7 C9 C10 -65.4(3) . . . . ?
C14 C9 C10 C11 0.5(5) . . . . ?
C7 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C10 C11 C12 Br1 178.8(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
Br1 C12 C13 C14 -178.0(2) . . . . ?
C10 C9 C14 C13 0.3(5) . . . . ?
C7 C9 C14 C13 -179.5(3) . . . . ?
C12 C13 C14 C9 -0.8(5) . . . . ?
C4 C5 C15 C16 -17.5(5) . . . . ?
C6 C5 C15 C16 167.3(4) . . . . ?
C5 C15 C16 C17 -169.2(4) . . . . ?
C15 C16 C17 C18 -172.6(5) . . . . ?

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
C8 H8B O3 0.99 2.43 3.393(4) 165.1 2_656
C8 H8A O1 0.99 2.40 3.190(4) 136.8 2_746
C8 H8A O1 0.99 2.40 3.190(4) 136.8 2_746
C8 H8B O3 0.99 2.43 3.393(4) 165.1 2_656

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.041

_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_d8v19933
_database_code_depnum_ccdc_archive 'CCDC 1978463'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 N3 O3'
_chemical_formula_weight         427.49

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'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.56750(10)
_cell_length_b                   28.7020(6)
_cell_length_c                   12.4932(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.5090(10)
_cell_angle_gamma                90
_cell_volume                     2322.61(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      7.808
_cell_measurement_theta_max      139.836

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6132
_exptl_absorpt_correction_T_max  0.7456
_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            31317
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.904
_diffrn_reflns_theta_max         67.466
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4115
_reflns_number_gt                3468
_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)+(0.0521P)²+0.4917P] 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       0.0066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4115
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.0007(2) 0.51719(5) 0.35620(13) 0.0885(5) Uani 1 1 d . . . . .
O2 O -0.0293(2) 0.32261(5) 0.27493(13) 0.0883(5) Uani 1 1 d . . . . .
O3 O 0.2219(3) 0.27369(5) 0.28512(14) 0.0978(5) Uani 1 1 d . . . . .
N1 N 0.1715(3) 0.45140(6) -0.05499(13) 0.0731(4) Uani 1 1 d . . . . .
N2 N 0.7245(2) 0.40113(7) 0.09750(15) 0.0829(5) Uani 1 1 d . . . . .
N3 N 0.1514(3) 0.31282(5) 0.27611(12) 0.0653(4) Uani 1 1 d . U . . .
C1 C 0.1275(2) 0.47447(5) 0.21888(13) 0.0479(4) Uani 1 1 d . . . . .
H1A H 0.0756 0.4837 0.1447 0.057 Uiso 1 1 calc R U . . .
H1B H 0.0379 0.4502 0.2386 0.057 Uiso 1 1 calc R U . . .
C2 C 0.1202(3) 0.51584(6) 0.29282(15) 0.0597(4) Uani 1 1 d . . . . .
C3 C 0.2666(3) 0.55433(6) 0.27998(19) 0.0758(5) Uani 1 1 d . . . . .
H3A H 0.2670 0.5767 0.3381 0.091 Uiso 1 1 calc R U . . .
H3B H 0.2212 0.5702 0.2117 0.091 Uiso 1 1 calc R U . . .
C4 C 0.4852(3) 0.53569(7) 0.28224(18) 0.0738(5) Uani 1 1 d . . . . .
H4A H 0.5727 0.5606 0.2634 0.089 Uiso 1 1 calc R U . . .
H4B H 0.5407 0.5254 0.3552 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4888(2) 0.49565(6) 0.20415(14) 0.0571(4) Uani 1 1 d . . . . .
H5A H 0.6295 0.4845 0.2095 0.069 Uiso 1 1 calc R U . . .
H5B H 0.4451 0.5069 0.1307 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3490(2) 0.45472(5) 0.22526(12) 0.0441(3) Uani 1 1 d . . . . .
C7 C 0.3491(2) 0.41744(5) 0.13178(11) 0.0431(3) Uani 1 1 d . . . . .
C8 C 0.2299(2) 0.37151(5) 0.14911(11) 0.0436(3) Uani 1 1 d . . . . .
H8 H 0.0843 0.3802 0.1444 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2993(2) 0.35251(5) 0.26363(12) 0.0486(4) Uani 1 1 d . U . . .
H9 H 0.4405 0.3405 0.2704 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2866(2) 0.38800(5) 0.35317(12) 0.0484(4) Uani 1 1 d . . . . .
H10 H 0.1428 0.3986 0.3433 0.058 Uiso 1 1 calc R U . . .
C11 C 0.4191(2) 0.43148(5) 0.33847(12) 0.0473(4) Uani 1 1 d . . . . .
H11 H 0.3870 0.4542 0.3918 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6521(2) 0.42227(7) 0.36817(15) 0.0645(5) Uani 1 1 d . . . . .
H12A H 0.6917 0.3987 0.3212 0.097 Uiso 1 1 calc R U . . .
H12B H 0.6836 0.4119 0.4421 0.097 Uiso 1 1 calc R U . . .
H12C H 0.7266 0.4505 0.3598 0.097 Uiso 1 1 calc R U . . .
C13 C 0.2483(2) 0.43716(5) 0.02634(13) 0.0506(4) Uani 1 1 d . . . . .
C14 C 0.5626(2) 0.40746(6) 0.11467(13) 0.0544(4) Uani 1 1 d . . . . .
C15 C 0.2389(2) 0.33544(5) 0.06113(13) 0.0531(4) Uani 1 1 d . . . . .
C16 C 0.0705(3) 0.33070(6) -0.02080(15) 0.0669(5) Uani 1 1 d . . . . .
H16 H -0.0447 0.3495 -0.0210 0.080 Uiso 1 1 calc R U . . .
C17 C 0.0723(4) 0.29809(8) -0.10255(18) 0.0902(7) Uani 1 1 d . . . . .
H17 H -0.0410 0.2955 -0.1577 0.108 Uiso 1 1 calc R U . . .
C18 C 0.2392(5) 0.26989(8) -0.1025(2) 0.0982(8) Uani 1 1 d . . . . .
H18 H 0.2394 0.2479 -0.1572 0.118 Uiso 1 1 calc R U . . .
C19 C 0.4066(5) 0.27389(8) -0.0218(2) 0.0947(8) Uani 1 1 d . . . . .
H19 H 0.5203 0.2546 -0.0220 0.114 Uiso 1 1 calc R U . . .
C20 C 0.4081(3) 0.30658(6) 0.06046(17) 0.0734(5) Uani 1 1 d . . . . .
H20 H 0.5225 0.3091 0.1150 0.088 Uiso 1 1 calc R U . . .
C21 C 0.3328(3) 0.36639(6) 0.46554(13) 0.0585(4) Uani 1 1 d . . . . .
C22 C 0.4908(4) 0.33433(7) 0.49500(16) 0.0858(6) Uani 1 1 d . . . . .
H22 H 0.5743 0.3258 0.4449 0.103 Uiso 1 1 calc R U . . .
C23 C 0.5254(5) 0.31495(9) 0.59726(19) 0.1067(9) Uani 1 1 d . . . . .
H23 H 0.6322 0.2937 0.6157 0.128 Uiso 1 1 calc R U . . .
C24 C 0.4041(5) 0.32679(10) 0.67168(19) 0.1079(9) Uani 1 1 d . . . . .
H24 H 0.4271 0.3134 0.7404 0.129 Uiso 1 1 calc R U . . .
C25 C 0.2486(4) 0.35838(10) 0.64472(18) 0.0965(8) Uani 1 1 d . . . . .
H25 H 0.1666 0.3667 0.6957 0.116 Uiso 1 1 calc R U . . .
C26 C 0.2116(3) 0.37823(7) 0.54189(15) 0.0705(5) Uani 1 1 d . . . . .
H26 H 0.1048 0.3996 0.5244 0.085 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 C2 1.204(2) . ?
O2 N3 1.217(2) . ?
O3 N3 1.2132(19) . ?
N1 C13 1.133(2) . ?
N2 C14 1.134(2) . ?
N3 C9 1.522(2) . ?
C1 C2 1.510(2) . ?
C1 C6 1.5511(18) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.491(2) . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5403(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.563(2) . ?
C6 C7 1.584(2) . ?
C7 C14 1.4806(19) . ?
C7 C13 1.485(2) . ?
C7 C8 1.5665(19) . ?
C8 C15 1.518(2) . ?
C8 C9 1.529(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.525(2) . ?
C9 H9 0.9800 . ?
C10 C21 1.519(2) . ?
C10 C11 1.550(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.537(2) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 C16 1.384(2) . ?
C15 C20 1.387(2) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.382(2) . ?
C21 C22 1.390(3) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
O3 N3 O2 124.87(17) . . ?
O3 N3 C9 117.50(16) . . ?
O2 N3 C9 117.63(14) . . ?
C2 C1 C6 112.35(12) . . ?
C2 C1 H1A 109.1 . . ?
C6 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C6 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C3 123.31(17) . . ?
O1 C2 C1 121.17(16) . . ?
C3 C2 C1 115.51(15) . . ?
C2 C3 C4 111.07(15) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.68(15) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 113.35(14) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C1 107.04(12) . . ?
C5 C6 C11 112.69(12) . . ?
C1 C6 C11 109.63(11) . . ?
C5 C6 C7 108.43(12) . . ?
C1 C6 C7 108.88(11) . . ?
C11 C6 C7 110.07(11) . . ?
C14 C7 C13 103.88(12) . . ?
C14 C7 C8 111.34(12) . . ?
C13 C7 C8 106.47(11) . . ?
C14 C7 C6 110.66(12) . . ?
C13 C7 C6 110.01(12) . . ?
C8 C7 C6 113.93(11) . . ?
C15 C8 C9 113.14(12) . . ?
C15 C8 C7 113.18(11) . . ?
C9 C8 C7 110.54(11) . . ?
C15 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C7 C8 H8 106.5 . . ?
N3 C9 C10 108.14(12) . . ?
N3 C9 C8 105.42(12) . . ?
C10 C9 C8 113.83(12) . . ?
N3 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
C21 C10 C9 112.22(12) . . ?
C21 C10 C11 114.08(13) . . ?
C9 C10 C11 110.54(12) . . ?
C21 C10 H10 106.5 . . ?
C9 C10 H10 106.5 . . ?
C11 C10 H10 106.5 . . ?
C12 C11 C10 112.90(13) . . ?
C12 C11 C6 115.12(12) . . ?
C10 C11 C6 111.34(11) . . ?
C12 C11 H11 105.5 . . ?
C10 C11 H11 105.5 . . ?
C6 C11 H11 105.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C7 178.70(18) . . ?
N2 C14 C7 176.83(19) . . ?
C16 C15 C20 118.68(17) . . ?
C16 C15 C8 118.71(14) . . ?
C20 C15 C8 122.61(15) . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.0(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C26 C21 C22 118.02(17) . . ?
C26 C21 C10 119.17(16) . . ?
C22 C21 C10 122.79(16) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.7(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.3(2) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -128.16(17) . . . . ?
C6 C1 C2 C3 52.89(19) . . . . ?
O1 C2 C3 C4 131.3(2) . . . . ?
C1 C2 C3 C4 -49.8(2) . . . . ?
C2 C3 C4 C5 50.8(2) . . . . ?
C3 C4 C5 C6 -57.3(2) . . . . ?
C4 C5 C6 C1 57.18(17) . . . . ?
C4 C5 C6 C11 -63.42(17) . . . . ?
C4 C5 C6 C7 174.49(13) . . . . ?
C2 C1 C6 C5 -53.47(17) . . . . ?
C2 C1 C6 C11 69.05(16) . . . . ?
C2 C1 C6 C7 -170.49(12) . . . . ?
C5 C6 C7 C14 47.99(15) . . . . ?
C1 C6 C7 C14 164.12(12) . . . . ?
C11 C6 C7 C14 -75.69(14) . . . . ?
C5 C6 C7 C13 -66.22(14) . . . . ?
C1 C6 C7 C13 49.91(14) . . . . ?
C11 C6 C7 C13 170.10(11) . . . . ?
C5 C6 C7 C8 174.34(11) . . . . ?
C1 C6 C7 C8 -69.53(14) . . . . ?
C11 C6 C7 C8 50.66(14) . . . . ?
C14 C7 C8 C15 -51.68(16) . . . . ?
C13 C7 C8 C15 60.89(15) . . . . ?
C6 C7 C8 C15 -177.67(12) . . . . ?
C14 C7 C8 C9 76.41(15) . . . . ?
C13 C7 C8 C9 -171.01(12) . . . . ?
C6 C7 C8 C9 -49.58(14) . . . . ?
O3 N3 C9 C10 -124.13(16) . . . . ?
O2 N3 C9 C10 56.78(18) . . . . ?
O3 N3 C9 C8 113.77(16) . . . . ?
O2 N3 C9 C8 -65.32(18) . . . . ?
C15 C8 C9 N3 -60.34(15) . . . . ?
C7 C8 C9 N3 171.55(11) . . . . ?
C15 C8 C9 C10 -178.69(12) . . . . ?
C7 C8 C9 C10 53.20(15) . . . . ?
N3 C9 C10 C21 56.58(16) . . . . ?
C8 C9 C10 C21 173.36(13) . . . . ?
N3 C9 C10 C11 -174.82(11) . . . . ?
C8 C9 C10 C11 -58.04(16) . . . . ?
C21 C10 C11 C12 54.26(17) . . . . ?
C9 C10 C11 C12 -73.32(16) . . . . ?
C21 C10 C11 C6 -174.46(12) . . . . ?
C9 C10 C11 C6 57.96(15) . . . . ?
C5 C6 C11 C12 -45.14(18) . . . . ?
C1 C6 C11 C12 -164.25(13) . . . . ?
C7 C6 C11 C12 76.02(15) . . . . ?
C5 C6 C11 C10 -175.27(12) . . . . ?
C1 C6 C11 C10 65.62(15) . . . . ?
C7 C6 C11 C10 -54.11(14) . . . . ?
C9 C8 C15 C16 132.69(15) . . . . ?
C7 C8 C15 C16 -100.58(16) . . . . ?
C9 C8 C15 C20 -46.3(2) . . . . ?
C7 C8 C15 C20 80.38(18) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?
C8 C15 C16 C17 -179.83(16) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C8 C15 C20 C19 179.40(17) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C9 C10 C21 C26 -137.28(16) . . . . ?
C11 C10 C21 C26 96.01(18) . . . . ?
C9 C10 C21 C22 41.6(2) . . . . ?
C11 C10 C21 C22 -85.1(2) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
C10 C21 C22 C23 -178.9(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C10 C21 C26 C25 178.97(18) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.026

_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_cd17080
_database_code_depnum_ccdc_archive 'CCDC 1957049'
loop_
_audit_author_name
_audit_author_address
'Jinxing Ye'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2021-06-07 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 H22 Br N O3'
_chemical_formula_weight         380.27

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      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                   5.5537(11)
_cell_length_b                   10.753(2)
_cell_length_c                   29.963(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1789.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2565
_cell_measurement_theta_min      5.438
_cell_measurement_theta_max      44.722

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             784
_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    2.311
_shelx_estimated_absorpt_T_min   0.655
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5127
_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            10277
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.359
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3326
_reflns_number_gt                2570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       '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)+(0.0451P)²+0.1441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 895 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.020(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3326
_refine_ls_number_parameters     228
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.93132(14) 1.05516(6) 1.03524(2) 0.0744(3) Uani 1 1 d . . . . .
N1 N 1.2808(10) 1.3980(4) 0.84576(14) 0.0541(12) Uani 1 1 d . . . . .
O1 O 1.5383(8) 0.8797(4) 0.75478(13) 0.0755(12) Uani 1 1 d . . . . .
O2 O 1.4854(9) 1.3675(4) 0.85252(13) 0.0750(13) Uani 1 1 d . . . . .
O3 O 1.2065(12) 1.5005(5) 0.8545(2) 0.126(2) Uani 1 1 d . . . . .
C1 C 1.1523(8) 1.1775(4) 0.83762(13) 0.0348(10) Uani 1 1 d . . . . .
H1 H 1.3210 1.1571 0.8315 0.042 Uiso 1 1 calc R U . . .
C2 C 1.1130(9) 1.3113(4) 0.82369(14) 0.0408(11) Uani 1 1 d . . . . .
H2A H 1.1328 1.3178 0.7916 0.049 Uiso 1 1 calc R U . . .
H2B H 0.9491 1.3352 0.8308 0.049 Uiso 1 1 calc R U . . .
C3 C 0.9947(8) 1.0893(4) 0.80890(13) 0.0366(11) Uani 1 1 d . . . . .
H3 H 0.8255 1.1103 0.8142 0.044 Uiso 1 1 calc R U . . .
C4 C 1.0440(11) 1.1014(5) 0.75838(14) 0.0509(13) Uani 1 1 d . . . . .
H4A H 0.9282 1.0515 0.7420 0.061 Uiso 1 1 calc R U . . .
H4B H 1.0232 1.1874 0.7494 0.061 Uiso 1 1 calc R U . . .
C5 C 1.2959(10) 1.0593(5) 0.74665(14) 0.0515(13) Uani 1 1 d . . . . .
H5A H 1.3088 1.0519 0.7145 0.062 Uiso 1 1 calc R U . . .
H5B H 1.4096 1.1224 0.7563 0.062 Uiso 1 1 calc R U . . .
C6 C 1.3636(9) 0.9371(5) 0.76759(15) 0.0490(12) Uani 1 1 d . . . . .
C7 C 1.2100(9) 0.8895(4) 0.80287(15) 0.0446(12) Uani 1 1 d . . . . .
H7 H 1.2369 0.8088 0.8128 0.053 Uiso 1 1 calc R U . . .
C8 C 1.0319(8) 0.9544(4) 0.82205(13) 0.0389(11) Uani 1 1 d . . . . .
C9 C 0.8655(10) 0.9003(5) 0.85611(15) 0.0495(13) Uani 1 1 d . . . . .
H9A H 0.8791 0.9497 0.8831 0.059 Uiso 1 1 calc R U . . .
H9B H 0.7021 0.9098 0.8452 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9010(16) 0.7670(6) 0.8685(2) 0.094(3) Uani 1 1 d D . . . .
H10A H 1.0608 0.7603 0.8804 0.112 Uiso 0.5 1 d R U P A 1
H10B H 0.8962 0.7191 0.8414 0.112 Uiso 0.5 1 d R U P A 1
H10C H 1.0521 0.7581 0.8836 0.112 Uiso 0.5 1 d R U P B 2
H10D H 0.8994 0.7160 0.8421 0.112 Uiso 0.5 1 d R U P B 2
C11 C 0.741(5) 0.704(2) 0.9028(7) 0.102(5) Uani 0.5 1 d D U P C 1
H11A H 0.5858 0.6853 0.8894 0.123 Uiso 0.5 1 calc R U P C 1
H11B H 0.8135 0.6259 0.9119 0.123 Uiso 0.5 1 calc R U P C 1
C12 C 0.704(5) 0.7839(17) 0.9429(6) 0.104(5) Uani 0.5 1 d D U P C 1
H12A H 0.8480 0.8301 0.9488 0.156 Uiso 0.5 1 calc R U P C 1
H12B H 0.6660 0.7325 0.9682 0.156 Uiso 0.5 1 calc R U P C 1
H12C H 0.5732 0.8405 0.9375 0.156 Uiso 0.5 1 calc R U P C 1
C11' C 0.690(5) 0.732(3) 0.9011(6) 0.103(5) Uani 0.5 1 d D U P C 2
H11C H 0.5558 0.7892 0.8975 0.123 Uiso 0.5 1 calc R U P C 2
H11D H 0.6345 0.6483 0.8958 0.123 Uiso 0.5 1 calc R U P C 2
C12' C 0.798(5) 0.7442(19) 0.9471(6) 0.109(5) Uani 0.5 1 d D U P C 2
H12D H 0.9405 0.6938 0.9490 0.163 Uiso 0.5 1 calc R U P C 2
H12E H 0.6834 0.7168 0.9690 0.163 Uiso 0.5 1 calc R U P C 2
H12F H 0.8394 0.8295 0.9527 0.163 Uiso 0.5 1 calc R U P C 2
C13 C 1.1104(8) 1.1579(4) 0.88744(13) 0.0338(10) Uani 1 1 d . . . . .
C14 C 1.2654(9) 1.0872(4) 0.91236(14) 0.0434(12) Uani 1 1 d . . . . .
H14 H 1.4065 1.0585 0.8992 0.052 Uiso 1 1 calc R U . . .
C15 C 1.2192(10) 1.0571(5) 0.95659(14) 0.0508(12) Uani 1 1 d . . . . .
H15 H 1.3272 1.0093 0.9730 0.061 Uiso 1 1 calc R U . . .
C16 C 1.0110(10) 1.0994(4) 0.97537(13) 0.0452(13) Uani 1 1 d . . . . .
C17 C 0.8556(10) 1.1724(5) 0.95252(15) 0.0495(13) Uani 1 1 d . . . . .
H17 H 0.7161 1.2019 0.9661 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9076(10) 1.2029(4) 0.90836(14) 0.0448(11) Uani 1 1 d . . . . .
H18 H 0.8034 1.2546 0.8927 0.054 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 1.908(4) . ?
N1 O2 1.200(6) . ?
N1 O3 1.205(6) . ?
N1 C2 1.475(7) . ?
O1 C6 1.213(6) . ?
C1 C2 1.514(6) . ?
C1 C13 1.525(6) . ?
C1 C3 1.551(6) . ?
C1 H1 0.9800 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.517(6) . ?
C3 C4 1.544(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.512(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.504(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.452(7) . ?
C7 C8 1.340(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.494(7) . ?
C9 C10 1.494(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.52(2) . ?
C10 C11' 1.57(2) . ?
C10 H10A 0.9596 . ?
C10 H10B 0.9612 . ?
C10 H10C 0.9586 . ?
C10 H10D 0.9618 . ?
C11 C12 1.49(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11' C12' 1.51(2) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13 C14 1.370(6) . ?
C13 C18 1.377(7) . ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.353(7) . ?
C17 C18 1.393(6) . ?
C17 H17 0.9300 . ?
C18 H18 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
O2 N1 O3 122.5(6) . . ?
O2 N1 C2 120.0(5) . . ?
O3 N1 C2 117.4(6) . . ?
C2 C1 C13 112.3(3) . . ?
C2 C1 C3 110.3(3) . . ?
C13 C1 C3 111.9(3) . . ?
C2 C1 H1 107.4 . . ?
C13 C1 H1 107.4 . . ?
C3 C1 H1 107.4 . . ?
N1 C2 C1 112.7(4) . . ?
N1 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C8 C3 C4 108.1(3) . . ?
C8 C3 C1 111.3(3) . . ?
C4 C3 C1 113.1(4) . . ?
C8 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C1 C3 H3 108.0 . . ?
C5 C4 C3 111.5(4) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 113.3(4) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O1 C6 C7 121.4(5) . . ?
O1 C6 C5 120.9(5) . . ?
C7 C6 C5 117.7(4) . . ?
C8 C7 C6 124.2(5) . . ?
C8 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?
C7 C8 C9 123.1(4) . . ?
C7 C8 C3 119.1(4) . . ?
C9 C8 C3 117.7(4) . . ?
C10 C9 C8 117.5(5) . . ?
C10 C9 H9A 107.9 . . ?
C8 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C8 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C9 C10 C11 121.3(12) . . ?
C9 C10 C11' 106.4(12) . . ?
C9 C10 H10A 106.6 . . ?
C11 C10 H10A 104.9 . . ?
C9 C10 H10B 107.5 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C9 C10 H10C 109.2 . . ?
C11' C10 H10C 109.6 . . ?
C9 C10 H10D 110.0 . . ?
C11' C10 H10D 111.7 . . ?
H10C C10 H10D 109.8 . . ?
C12 C11 C10 112(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12' C11' C10 105(2) . . ?
C12' C11' H11C 110.8 . . ?
C10 C11' H11C 110.8 . . ?
C12' C11' H11D 110.8 . . ?
C10 C11' H11D 110.8 . . ?
H11C C11' H11D 108.9 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C14 C13 C18 117.4(4) . . ?
C14 C13 C1 120.9(4) . . ?
C18 C13 C1 121.5(4) . . ?
C13 C14 C15 122.3(5) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 118.2(5) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C17 C16 C15 121.7(4) . . ?
C17 C16 Br1 118.2(4) . . ?
C15 C16 Br1 120.1(4) . . ?
C16 C17 C18 119.0(5) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 121.3(5) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 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
O2 N1 C2 C1 37.1(6) . . . . ?
O3 N1 C2 C1 -146.2(5) . . . . ?
C13 C1 C2 N1 61.9(5) . . . . ?
C3 C1 C2 N1 -172.6(4) . . . . ?
C2 C1 C3 C8 179.7(4) . . . . ?
C13 C1 C3 C8 -54.6(5) . . . . ?
C2 C1 C3 C4 57.7(5) . . . . ?
C13 C1 C3 C4 -176.6(4) . . . . ?
C8 C3 C4 C5 -58.2(5) . . . . ?
C1 C3 C4 C5 65.6(5) . . . . ?
C3 C4 C5 C6 46.9(6) . . . . ?
C4 C5 C6 O1 165.6(4) . . . . ?
C4 C5 C6 C7 -13.1(6) . . . . ?
O1 C6 C7 C8 171.9(5) . . . . ?
C5 C6 C7 C8 -9.4(7) . . . . ?
C6 C7 C8 C9 175.7(4) . . . . ?
C6 C7 C8 C3 -4.2(7) . . . . ?
C4 C3 C8 C7 37.4(6) . . . . ?
C1 C3 C8 C7 -87.4(5) . . . . ?
C4 C3 C8 C9 -142.5(4) . . . . ?
C1 C3 C8 C9 92.7(5) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C3 C8 C9 C10 179.2(5) . . . . ?
C8 C9 C10 C11 180.0(13) . . . . ?
C8 C9 C10 C11' -175.1(10) . . . . ?
C9 C10 C11 C12 -45(3) . . . . ?
C11' C10 C11 C12 -63(5) . . . . ?
C9 C10 C11' C12' -98(2) . . . . ?
C11 C10 C11' C12' 66(6) . . . . ?
C2 C1 C13 C14 -136.2(5) . . . . ?
C3 C1 C13 C14 99.1(5) . . . . ?
C2 C1 C13 C18 48.4(6) . . . . ?
C3 C1 C13 C18 -76.2(5) . . . . ?
C18 C13 C14 C15 2.4(7) . . . . ?
C1 C13 C14 C15 -173.2(4) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C14 C15 C16 C17 -2.2(8) . . . . ?
C14 C15 C16 Br1 177.4(4) . . . . ?
C15 C16 C17 C18 1.4(8) . . . . ?
Br1 C16 C17 C18 -178.3(4) . . . . ?
C14 C13 C18 C17 -3.3(7) . . . . ?
C1 C13 C18 C17 172.3(4) . . . . ?
C16 C17 C18 C13 1.5(8) . . . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.051

_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_dm14528_0m
_database_code_depnum_ccdc_archive 'CCDC 1978462'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2014-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H20 Cl N O3'
_chemical_formula_sum            'C24 H20 Cl N O3'
_chemical_formula_weight         405.86
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.9525(7)
_cell_length_b                   13.3638(9)
_cell_length_c                   13.3808(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1958.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6499
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0482 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.9369.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19828
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.154
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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         0.781
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5344
_reflns_number_total             5979
_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.
;
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2141 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.41901(5) 0.66577(4) 0.87545(4) 0.03688(13) Uani 1 1 d . . . . .
O1 O 1.39146(14) 0.96649(12) 0.88466(11) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.90448(16) 1.11697(10) 0.60532(11) 0.0362(3) Uani 1 1 d . . . . .
O3 O 1.00158(13) 0.80700(10) 0.49126(10) 0.0291(3) Uani 1 1 d . . . . .
N1 N 0.92718(15) 0.95969(11) 0.53921(11) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.71537(17) 0.71735(15) 0.71068(14) 0.0262(4) Uani 1 1 d . . . . .
H1 H 0.7409 0.7059 0.6438 0.031 Uiso 1 1 calc R . . . .
C2 C 0.59900(19) 0.68803(15) 0.73979(14) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.5450 0.6573 0.6935 0.034 Uiso 1 1 calc R . . . .
C3 C 0.56350(18) 0.70445(14) 0.83727(14) 0.0253(4) Uani 1 1 d . . . . .
C4 C 0.63937(18) 0.75074(14) 0.90527(14) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.6128 0.7624 0.9718 0.032 Uiso 1 1 calc R . . . .
C5 C 0.75459(17) 0.77992(14) 0.87515(15) 0.0258(4) Uani 1 1 d . . . . .
H5 H 0.8071 0.8120 0.9217 0.031 Uiso 1 1 calc R . . . .
C6 C 0.79550(16) 0.76313(13) 0.77740(13) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.91838(17) 0.78923(13) 0.74392(13) 0.0221(3) Uani 1 1 d . . . . .
H7 H 0.9393 0.7738 0.6767 0.027 Uiso 1 1 calc R . . . .
C8 C 1.00379(16) 0.83305(14) 0.80035(13) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.9812 0.8498 0.8668 0.027 Uiso 1 1 calc R . . . .
C9 C 1.12744(16) 0.85761(12) 0.77036(13) 0.0205(3) Uani 1 1 d . . . . .
C10 C 1.20292(17) 0.89805(14) 0.83956(14) 0.0245(4) Uani 1 1 d . . . . .
H10 H 1.1722 0.9071 0.9053 0.029 Uiso 1 1 calc R . . . .
C11 C 1.32885(18) 0.92874(15) 0.81957(14) 0.0260(4) Uani 1 1 d . . . . .
C12 C 1.37490(18) 0.91371(16) 0.71495(15) 0.0292(4) Uani 1 1 d . . . . .
H12A H 1.4638 0.9004 0.7168 0.035 Uiso 1 1 calc R . . . .
H12B H 1.3616 0.9757 0.6759 0.035 Uiso 1 1 calc R . . . .
C13 C 1.31058(17) 0.82714(16) 0.66371(15) 0.0282(4) Uani 1 1 d . . . . .
H13A H 1.3327 0.7639 0.6978 0.034 Uiso 1 1 calc R . . . .
H13B H 1.3390 0.8226 0.5936 0.034 Uiso 1 1 calc R . . . .
C14 C 1.17177(15) 0.83911(13) 0.66480(13) 0.0209(3) Uani 1 1 d . . . . .
H14 H 1.1362 0.7738 0.6427 0.025 Uiso 1 1 calc R . . . .
C15 C 1.12806(17) 0.91989(14) 0.58912(13) 0.0229(3) Uani 1 1 d . . . . .
H15 H 1.1944 0.9281 0.5385 0.028 Uiso 1 1 calc R . . . .
C16 C 1.0950(2) 1.02480(13) 0.62651(15) 0.0296(4) Uani 1 1 d . . . . .
H16A H 1.0997 1.0278 0.7003 0.036 Uiso 1 1 calc R . . . .
H16B H 1.1514 1.0753 0.5982 0.036 Uiso 1 1 calc R . . . .
C17 C 0.96635(19) 1.04368(14) 0.59157(13) 0.0259(4) Uani 1 1 d . . . . .
C18 C 1.01512(17) 0.88599(14) 0.53348(13) 0.0223(3) Uani 1 1 d . . . . .
C19 C 0.81259(17) 0.95256(13) 0.48827(13) 0.0222(3) Uani 1 1 d . . . . .
C20 C 0.70727(19) 0.93592(16) 0.54198(16) 0.0315(4) Uani 1 1 d . . . . .
H20 H 0.7097 0.9315 0.6128 0.038 Uiso 1 1 calc R . . . .
C21 C 0.5978(2) 0.92570(17) 0.49128(19) 0.0380(5) Uani 1 1 d . . . . .
H21 H 0.5244 0.9150 0.5275 0.046 Uiso 1 1 calc R . . . .
C22 C 0.59498(19) 0.93105(15) 0.38847(19) 0.0356(5) Uani 1 1 d . . . . .
H22 H 0.5196 0.9238 0.3540 0.043 Uiso 1 1 calc R . . . .
C23 C 0.7011(2) 0.94690(17) 0.33542(17) 0.0351(5) Uani 1 1 d . . . . .
H23 H 0.6988 0.9497 0.2645 0.042 Uiso 1 1 calc R . . . .
C24 C 0.81084(18) 0.95872(15) 0.38494(15) 0.0293(4) Uani 1 1 d . . . . .
H24 H 0.8839 0.9709 0.3487 0.035 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
Cl1 C3 1.7414(19) . ?
O1 C11 1.218(2) . ?
O2 C17 1.205(2) . ?
O3 C18 1.206(2) . ?
N1 C17 1.391(2) . ?
N1 C18 1.380(2) . ?
N1 C19 1.431(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(3) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C6 C7 1.461(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.337(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.450(2) . ?
C9 C10 1.354(2) . ?
C9 C14 1.514(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.464(3) . ?
C11 C12 1.501(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.529(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.556(3) . ?
C15 H15 1.0000 . ?
C15 C16 1.532(3) . ?
C15 C18 1.513(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.506(3) . ?
C19 C20 1.377(3) . ?
C19 C24 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 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
C17 N1 C19 124.34(16) . . ?
C18 N1 C17 112.88(16) . . ?
C18 N1 C19 122.55(14) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C6 121.47(18) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.63(18) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 Cl1 119.11(15) . . ?
C4 C3 Cl1 119.17(15) . . ?
C4 C3 C2 121.72(18) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.01(18) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.30(17) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.85(16) . . ?
C1 C6 C7 119.25(16) . . ?
C5 C6 C7 122.88(16) . . ?
C6 C7 H7 117.4 . . ?
C8 C7 C6 125.16(17) . . ?
C8 C7 H7 117.4 . . ?
C7 C8 H8 116.7 . . ?
C7 C8 C9 126.59(17) . . ?
C9 C8 H8 116.7 . . ?
C8 C9 C14 121.38(15) . . ?
C10 C9 C8 118.12(17) . . ?
C10 C9 C14 120.49(16) . . ?
C9 C10 H10 117.9 . . ?
C9 C10 C11 124.22(17) . . ?
C11 C10 H10 117.9 . . ?
O1 C11 C10 121.06(18) . . ?
O1 C11 C12 122.21(18) . . ?
C10 C11 C12 116.71(16) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C11 C12 C13 111.54(17) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.17(16) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C9 C14 C13 110.18(15) . . ?
C9 C14 H14 107.1 . . ?
C9 C14 C15 113.28(14) . . ?
C13 C14 H14 107.1 . . ?
C13 C14 C15 111.87(15) . . ?
C15 C14 H14 107.1 . . ?
C14 C15 H15 107.1 . . ?
C16 C15 C14 119.69(15) . . ?
C16 C15 H15 107.1 . . ?
C18 C15 C14 111.36(14) . . ?
C18 C15 H15 107.1 . . ?
C18 C15 C16 103.97(15) . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 C15 105.85(15) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
O2 C17 N1 124.01(19) . . ?
O2 C17 C16 127.95(18) . . ?
N1 C17 C16 108.05(16) . . ?
O3 C18 N1 124.40(17) . . ?
O3 C18 C15 126.35(17) . . ?
N1 C18 C15 109.25(15) . . ?
C20 C19 N1 119.78(16) . . ?
C20 C19 C24 121.25(18) . . ?
C24 C19 N1 118.92(16) . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.1(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 120.5 . . ?
C23 C24 C19 118.95(19) . . ?
C23 C24 H24 120.5 . . ?

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
Cl1 C3 C4 C5 179.01(15) . . . . ?
O1 C11 C12 C13 153.5(2) . . . . ?
N1 C19 C20 C21 -177.74(18) . . . . ?
N1 C19 C24 C23 176.83(18) . . . . ?
C1 C2 C3 Cl1 -178.70(15) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C1 C6 C7 C8 -179.87(18) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 C7 177.82(17) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -177.44(17) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C7 C8 C9 178.29(17) . . . . ?
C7 C8 C9 C10 -177.11(18) . . . . ?
C7 C8 C9 C14 3.0(3) . . . . ?
C8 C9 C10 C11 -178.49(17) . . . . ?
C8 C9 C14 C13 -155.32(16) . . . . ?
C8 C9 C14 C15 78.5(2) . . . . ?
C9 C10 C11 O1 178.58(19) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C14 C15 C16 24.6(2) . . . . ?
C9 C14 C15 C18 -96.84(18) . . . . ?
C10 C9 C14 C13 24.8(2) . . . . ?
C10 C9 C14 C15 -101.33(19) . . . . ?
C10 C11 C12 C13 -28.1(3) . . . . ?
C11 C12 C13 C14 54.9(2) . . . . ?
C12 C13 C14 C9 -52.7(2) . . . . ?
C12 C13 C14 C15 74.3(2) . . . . ?
C13 C14 C15 C16 -100.7(2) . . . . ?
C13 C14 C15 C18 137.90(16) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C14 C15 C16 C17 -124.31(17) . . . . ?
C14 C15 C18 O3 -50.2(2) . . . . ?
C14 C15 C18 N1 129.05(16) . . . . ?
C15 C16 C17 O2 179.45(19) . . . . ?
C15 C16 C17 N1 -0.06(19) . . . . ?
C16 C15 C18 O3 179.65(18) . . . . ?
C16 C15 C18 N1 -1.13(19) . . . . ?
C17 N1 C18 O3 -179.58(18) . . . . ?
C17 N1 C18 C15 1.2(2) . . . . ?
C17 N1 C19 C20 -77.6(2) . . . . ?
C17 N1 C19 C24 104.9(2) . . . . ?
C18 N1 C17 O2 179.77(18) . . . . ?
C18 N1 C17 C16 -0.7(2) . . . . ?
C18 N1 C19 C20 108.4(2) . . . . ?
C18 N1 C19 C24 -69.1(2) . . . . ?
C18 C15 C16 C17 0.70(19) . . . . ?
C19 N1 C17 O2 5.2(3) . . . . ?
C19 N1 C17 C16 -175.22(16) . . . . ?
C19 N1 C18 O3 -4.9(3) . . . . ?
C19 N1 C18 C15 175.81(15) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C19 C24 C23 -0.6(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C19 1.2(3) . . . . ?
C24 C19 C20 C21 -0.3(3) . . . . ?

_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_d8v191001_0m
_database_code_depnum_ccdc_archive 'CCDC 1978464'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N4 O3'
_chemical_formula_weight         468.54

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

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

_cell_length_a                   24.6130(6)
_cell_length_b                   24.6130(6)
_cell_length_c                   8.0200(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4207.6(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      8.296
_cell_measurement_theta_max      140.125

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_F_000             1488
_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    0.590
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5333
_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            69597
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.491
_diffrn_reflns_theta_max         66.976
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4925
_reflns_number_gt                4693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.957

_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)+(0.0532P)²+0.3003P] 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       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2020 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4925
_refine_ls_number_parameters     319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.000 0.000 -0.042 506 29 ' '
2 0.333 0.667 -0.141 58 2 ' '
3 0.667 0.333 0.359 58 2 ' '
_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
O1 O 0.79243(10) 0.71090(10) 0.9482(2) 0.0744(6) Uani 1 1 d . . . . .
O2 O 0.67898(10) 0.55334(9) 0.0512(2) 0.0761(6) Uani 1 1 d . . . . .
O3 O 0.64202(10) 0.47463(9) 0.2159(3) 0.0834(6) Uani 1 1 d . . . . .
N1 N 0.91730(11) 0.73413(11) 0.3848(4) 0.0763(7) Uani 1 1 d . . . . .
N2 N 0.80275(13) 0.60067(12) 0.7280(3) 0.0752(7) Uani 1 1 d . . . . .
N3 N 0.67036(9) 0.53045(9) 0.1885(3) 0.0522(5) Uani 1 1 d . . . . .
C1 C 0.76216(12) 0.70389(11) 0.8228(3) 0.0540(6) Uani 1 1 d . . . . .
C2 C 0.69272(12) 0.66547(12) 0.8158(3) 0.0556(6) Uani 1 1 d . . . . .
H2A H 0.6752 0.6930 0.8112 0.067 Uiso 1 1 calc R U . . .
H2B H 0.6775 0.6406 0.9167 0.067 Uiso 1 1 calc R U . . .
C3 C 0.67023(10) 0.62194(11) 0.6647(3) 0.0471(5) Uani 1 1 d . . . . .
H3A H 0.6247 0.5991 0.6620 0.057 Uiso 1 1 calc R U . . .
H3B H 0.6843 0.5917 0.6743 0.057 Uiso 1 1 calc R U . . .
C4 C 0.69553(9) 0.65928(10) 0.5023(3) 0.0405(5) Uani 1 1 d . . . . .
H4 H 0.6789 0.6880 0.4984 0.049 Uiso 1 1 calc R U . . .
C5 C 0.76786(9) 0.70162(9) 0.4961(2) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.79342(11) 0.73742(11) 0.6626(3) 0.0490(5) Uani 1 1 d . . . . .
H6A H 0.8375 0.7500 0.6699 0.059 Uiso 1 1 calc R U . . .
H6B H 0.7909 0.7755 0.6570 0.059 Uiso 1 1 calc R U . . .
C7 C 0.79917(9) 0.65974(10) 0.4606(2) 0.0410(5) Uani 1 1 d . . . . .
C8 C 0.76840(9) 0.61210(9) 0.3118(3) 0.0407(4) Uani 1 1 d . . . . .
H8 H 0.7758 0.6374 0.2111 0.049 Uiso 1 1 calc R U . . .
C9 C 0.69734(10) 0.57431(10) 0.3357(3) 0.0422(5) Uani 1 1 d . . . . .
H9 H 0.6874 0.5499 0.4391 0.051 Uiso 1 1 calc R U . . .
C10 C 0.67022(9) 0.61811(10) 0.3428(3) 0.0417(5) Uani 1 1 d . . . . .
H10 H 0.6876 0.6466 0.2474 0.050 Uiso 1 1 calc R U . . .
C11 C 0.59920(10) 0.58687(11) 0.3293(3) 0.0476(5) Uani 1 1 d . . . . .
C12 C 0.55810(11) 0.53058(12) 0.4054(3) 0.0596(6) Uani 1 1 d . . . . .
H12 H 0.5738 0.5081 0.4607 0.072 Uiso 1 1 calc R U . . .
C13 C 0.49423(12) 0.50730(15) 0.4003(4) 0.0716(8) Uani 1 1 d . . . . .
H13 H 0.4673 0.4694 0.4524 0.086 Uiso 1 1 calc R U . . .
C14 C 0.47018(13) 0.53918(16) 0.3199(4) 0.0758(8) Uani 1 1 d . . . . .
H14 H 0.4271 0.5236 0.3193 0.091 Uiso 1 1 calc R U . . .
C15 C 0.50939(13) 0.59419(16) 0.2397(4) 0.0721(8) Uani 1 1 d . . . . .
H15 H 0.4929 0.6155 0.1828 0.087 Uiso 1 1 calc R U . . .
C16 C 0.57404(12) 0.61830(13) 0.2433(3) 0.0577(6) Uani 1 1 d . . . . .
H16 H 0.6005 0.6556 0.1880 0.069 Uiso 1 1 calc R U . . .
C17 C 0.78864(11) 0.75130(10) 0.3546(3) 0.0490(5) Uani 1 1 d . . . . .
H17A H 0.8329 0.7813 0.3691 0.059 Uiso 1 1 calc R U . . .
H17B H 0.7840 0.7303 0.2489 0.059 Uiso 1 1 calc R U . . .
C18 C 0.75336(15) 0.78719(13) 0.3444(4) 0.0711(7) Uani 1 1 d . . . . .
H18A H 0.7740 0.8212 0.2666 0.107 Uiso 1 1 calc R U . . .
H18B H 0.7526 0.8036 0.4524 0.107 Uiso 1 1 calc R U . . .
H18C H 0.7112 0.7595 0.3077 0.107 Uiso 1 1 calc R U . . .
C19 C 0.86625(11) 0.70174(11) 0.4186(3) 0.0506(5) Uani 1 1 d . . . . .
C20 C 0.80016(11) 0.62579(11) 0.6124(3) 0.0499(5) Uani 1 1 d . . . . .
C21 C 0.79926(10) 0.57287(10) 0.2825(3) 0.0435(5) Uani 1 1 d . . . . .
C22 C 0.84458(11) 0.59072(11) 0.1604(3) 0.0566(6) Uani 1 1 d . . . . .
H22 H 0.8554 0.6262 0.0964 0.068 Uiso 1 1 calc R U . . .
C23 C 0.87408(13) 0.55618(14) 0.1324(5) 0.0761(9) Uani 1 1 d . . . . .
H23 H 0.9050 0.5691 0.0508 0.091 Uiso 1 1 calc R U . . .
C24 C 0.85856(14) 0.50373(15) 0.2221(5) 0.0763(8) Uani 1 1 d . . . . .
H24 H 0.8788 0.4810 0.2020 0.092 Uiso 1 1 calc R U . . .
C25 C 0.81289(15) 0.48409(13) 0.3430(4) 0.0723(8) Uani 1 1 d . . . . .
H25 H 0.8019 0.4479 0.4041 0.087 Uiso 1 1 calc R U . . .
C26 C 0.78325(12) 0.51859(12) 0.3733(3) 0.0587(6) Uani 1 1 d . . . . .
H26 H 0.7524 0.5053 0.4551 0.070 Uiso 1 1 calc R U . . .
N4 N 0.3477(2) 0.5563(3) 0.1679(7) 0.1548(18) Uani 1 1 d . . . . .
C27 C 0.3146(2) 0.5546(2) 0.2703(7) 0.1076(13) Uani 1 1 d . . . . .
C28 C 0.2712(3) 0.5491(2) 0.3972(7) 0.1225(15) Uani 1 1 d . . . . .
H28A H 0.2429 0.5616 0.3529 0.184 Uiso 1 1 calc R U . . .
H28B H 0.2938 0.5757 0.4895 0.184 Uiso 1 1 calc R U . . .
H28C H 0.2479 0.5063 0.4343 0.184 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 C1 1.212(3) . ?
O2 N3 1.206(3) . ?
O3 N3 1.210(3) . ?
N1 C19 1.134(3) . ?
N2 C20 1.133(3) . ?
N3 C9 1.511(3) . ?
C1 C2 1.484(4) . ?
C1 C6 1.513(3) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.535(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.550(3) . ?
C4 C10 1.555(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.549(3) . ?
C5 C17 1.555(3) . ?
C5 C7 1.591(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C20 1.484(3) . ?
C7 C19 1.484(3) . ?
C7 C8 1.577(3) . ?
C8 C21 1.516(3) . ?
C8 C9 1.528(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.527(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.521(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.383(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.359(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.519(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C21 C22 1.381(3) . ?
C21 C26 1.394(3) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N4 C27 1.143(7) . ?
C27 C28 1.431(8) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
O2 N3 O3 124.3(2) . . ?
O2 N3 C9 117.88(19) . . ?
O3 N3 C9 117.8(2) . . ?
O1 C1 C2 123.5(2) . . ?
O1 C1 C6 121.2(2) . . ?
C2 C1 C6 115.2(2) . . ?
C1 C2 C3 112.05(19) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 110.93(18) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 114.53(17) . . ?
C3 C4 C10 113.40(17) . . ?
C5 C4 C10 111.29(16) . . ?
C3 C4 H4 105.6 . . ?
C5 C4 H4 105.6 . . ?
C10 C4 H4 105.6 . . ?
C6 C5 C4 110.99(17) . . ?
C6 C5 C17 107.54(17) . . ?
C4 C5 C17 111.55(17) . . ?
C6 C5 C7 109.39(17) . . ?
C4 C5 C7 109.61(15) . . ?
C17 C5 C7 107.66(16) . . ?
C1 C6 C5 118.06(18) . . ?
C1 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
C1 C6 H6B 107.8 . . ?
C5 C6 H6B 107.8 . . ?
H6A C6 H6B 107.1 . . ?
C20 C7 C19 104.66(18) . . ?
C20 C7 C8 109.85(17) . . ?
C19 C7 C8 107.43(16) . . ?
C20 C7 C5 111.58(16) . . ?
C19 C7 C5 108.65(17) . . ?
C8 C7 C5 114.14(16) . . ?
C21 C8 C9 114.67(17) . . ?
C21 C8 C7 112.56(16) . . ?
C9 C8 C7 109.62(16) . . ?
C21 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C7 C8 H8 106.5 . . ?
N3 C9 C10 110.03(17) . . ?
N3 C9 C8 107.29(16) . . ?
C10 C9 C8 110.26(16) . . ?
N3 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C11 C10 C9 115.97(17) . . ?
C11 C10 C4 111.87(16) . . ?
C9 C10 C4 108.47(16) . . ?
C11 C10 H10 106.7 . . ?
C9 C10 H10 106.7 . . ?
C4 C10 H10 106.7 . . ?
C12 C11 C16 118.0(2) . . ?
C12 C11 C10 123.7(2) . . ?
C16 C11 C10 118.2(2) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.3(3) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C5 115.95(19) . . ?
C18 C17 H17A 108.3 . . ?
C5 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C5 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C7 179.1(3) . . ?
N2 C20 C7 178.0(3) . . ?
C22 C21 C26 118.1(2) . . ?
C22 C21 C8 119.3(2) . . ?
C26 C21 C8 122.5(2) . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N4 C27 C28 177.1(6) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O1 C1 C2 C3 -133.6(2) . . . . ?
C6 C1 C2 C3 49.6(3) . . . . ?
C1 C2 C3 C4 -56.6(3) . . . . ?
C2 C3 C4 C5 55.1(2) . . . . ?
C2 C3 C4 C10 -175.71(18) . . . . ?
C3 C4 C5 C6 -43.9(2) . . . . ?
C10 C4 C5 C6 -174.20(17) . . . . ?
C3 C4 C5 C17 -163.84(17) . . . . ?
C10 C4 C5 C17 65.9(2) . . . . ?
C3 C4 C5 C7 77.0(2) . . . . ?
C10 C4 C5 C7 -53.3(2) . . . . ?
O1 C1 C6 C5 142.5(2) . . . . ?
C2 C1 C6 C5 -40.7(3) . . . . ?
C4 C5 C6 C1 36.5(3) . . . . ?
C17 C5 C6 C1 158.8(2) . . . . ?
C7 C5 C6 C1 -84.6(2) . . . . ?
C6 C5 C7 C20 44.5(2) . . . . ?
C4 C5 C7 C20 -77.4(2) . . . . ?
C17 C5 C7 C20 161.10(18) . . . . ?
C6 C5 C7 C19 -70.4(2) . . . . ?
C4 C5 C7 C19 167.74(17) . . . . ?
C17 C5 C7 C19 46.2(2) . . . . ?
C6 C5 C7 C8 169.80(17) . . . . ?
C4 C5 C7 C8 47.9(2) . . . . ?
C17 C5 C7 C8 -73.6(2) . . . . ?
C20 C7 C8 C21 -53.5(2) . . . . ?
C19 C7 C8 C21 59.8(2) . . . . ?
C5 C7 C8 C21 -179.71(17) . . . . ?
C20 C7 C8 C9 75.4(2) . . . . ?
C19 C7 C8 C9 -171.34(17) . . . . ?
C5 C7 C8 C9 -50.8(2) . . . . ?
O2 N3 C9 C10 59.7(3) . . . . ?
O3 N3 C9 C10 -121.0(2) . . . . ?
O2 N3 C9 C8 -60.3(2) . . . . ?
O3 N3 C9 C8 119.0(2) . . . . ?
C21 C8 C9 N3 -53.3(2) . . . . ?
C7 C8 C9 N3 179.01(16) . . . . ?
C21 C8 C9 C10 -173.07(17) . . . . ?
C7 C8 C9 C10 59.2(2) . . . . ?
N3 C9 C10 C11 49.4(2) . . . . ?
C8 C9 C10 C11 167.50(18) . . . . ?
N3 C9 C10 C4 176.19(17) . . . . ?
C8 C9 C10 C4 -65.7(2) . . . . ?
C3 C4 C10 C11 61.3(2) . . . . ?
C5 C4 C10 C11 -167.90(17) . . . . ?
C3 C4 C10 C9 -67.9(2) . . . . ?
C5 C4 C10 C9 62.9(2) . . . . ?
C9 C10 C11 C12 39.8(3) . . . . ?
C4 C10 C11 C12 -85.3(3) . . . . ?
C9 C10 C11 C16 -143.9(2) . . . . ?
C4 C10 C11 C16 91.0(2) . . . . ?
C16 C11 C12 C13 -1.9(4) . . . . ?
C10 C11 C12 C13 174.4(2) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 1.5(5) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C12 C11 C16 C15 2.1(4) . . . . ?
C10 C11 C16 C15 -174.5(2) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C6 C5 C17 C18 -74.6(2) . . . . ?
C4 C5 C17 C18 47.4(3) . . . . ?
C7 C5 C17 C18 167.7(2) . . . . ?
C9 C8 C21 C22 136.6(2) . . . . ?
C7 C8 C21 C22 -97.2(2) . . . . ?
C9 C8 C21 C26 -42.8(3) . . . . ?
C7 C8 C21 C26 83.5(3) . . . . ?
C26 C21 C22 C23 -1.4(4) . . . . ?
C8 C21 C22 C23 179.2(2) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
C24 C25 C26 C21 0.1(4) . . . . ?
C22 C21 C26 C25 0.9(4) . . . . ?
C8 C21 C26 C25 -179.7(2) . . . . ?

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
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556
C2 H2B O2 0.97 2.42 3.219(3) 139.5 1_556

_refine_diff_density_max         0.129
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

