# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zd_20190610_2_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1921882'
loop_
_audit_author_name
_audit_author_address
'Dong Zhang'
;SiChuan University
China
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Br Cl0 N2 O3'
_chemical_formula_weight         449.29

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'
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'

_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                   7.7448(13)
_cell_length_b                   15.656(3)
_cell_length_c                   18.122(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2197.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    235(2)
_cell_measurement_reflns_used    5659
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.43

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.895
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5818
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71073    7.756   15.690   18.100   90.009   90.026   89.849
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      235(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23675
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         28.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5508
_reflns_number_gt                3763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.992

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1693P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5508
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.738
_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 0.52644(10) 0.67436(4) 0.79264(4) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.1143(7) 0.5654(3) 0.6832(3) 0.0458(11) Uani 1 1 d . . . . .
O1 O -0.0038(5) 0.3789(2) 0.6550(2) 0.0469(9) Uani 1 1 d . . . . .
C1 C 0.1176(10) 0.1307(4) 0.5899(4) 0.0619(18) Uani 1 1 d . . . . .
H1 H 0.102042 0.085187 0.623143 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1607(9) 0.1137(5) 0.5159(5) 0.067(2) Uani 1 1 d . . . . .
H2 H 0.175672 0.057371 0.499247 0.081 Uiso 1 1 calc R U . . .
O2 O 0.0088(5) 0.4155(3) 0.7735(2) 0.0491(9) Uani 1 1 d . . . . .
N2 N 0.6519(7) 0.4610(3) 0.7595(3) 0.0451(11) Uani 1 1 d . . . . .
H2A H 0.758979 0.446528 0.752189 0.054 Uiso 1 1 calc R U . . .
C3 C 0.0983(9) 0.2136(4) 0.6139(4) 0.0507(14) Uani 1 1 d . . . . .
H3 H 0.070014 0.224039 0.663512 0.061 Uiso 1 1 calc R U . . .
O3 O 0.5948(6) 0.5183(3) 0.6448(2) 0.0497(10) Uani 1 1 d . . . . .
C4 C 0.1802(9) 0.1817(5) 0.4687(4) 0.067(2) Uani 1 1 d . . . . .
H4 H 0.205931 0.171427 0.418752 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1626(9) 0.2652(5) 0.4932(4) 0.0537(15) Uani 1 1 d . . . . .
H5 H 0.179694 0.310716 0.460184 0.064 Uiso 1 1 calc R U . . .
C6 C 0.1199(7) 0.2819(4) 0.5661(3) 0.0405(12) Uani 1 1 d . . . . .
C7 C 0.1080(8) 0.3737(4) 0.5918(3) 0.0446(12) Uani 1 1 d . . . . .
H7 H 0.057632 0.408453 0.551535 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2800(8) 0.4128(4) 0.6139(3) 0.0452(12) Uani 1 1 d . . . . .
H8A H 0.293088 0.470120 0.592976 0.054 Uiso 1 1 calc R U . . .
H8B H 0.376374 0.377068 0.597210 0.054 Uiso 1 1 calc R U . . .
C9 C 0.2727(7) 0.4163(3) 0.6977(3) 0.0385(11) Uani 1 1 d . . . . .
H9 H 0.330771 0.364101 0.716117 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0821(7) 0.4065(3) 0.7150(3) 0.0402(11) Uani 1 1 d . . . . .
C11 C 0.2631(7) 0.5756(3) 0.7193(3) 0.0374(10) Uani 1 1 d . . . . .
C12 C 0.3206(9) 0.6579(4) 0.7389(4) 0.0488(13) Uani 1 1 d . . . . .
C13 C 0.2226(10) 0.7282(4) 0.7193(4) 0.0558(16) Uani 1 1 d . . . . .
H13 H 0.260543 0.783594 0.731117 0.067 Uiso 1 1 calc R U . . .
C14 C 0.0688(11) 0.7165(4) 0.6824(4) 0.0588(17) Uani 1 1 d . . . . .
H14 H 0.000673 0.763569 0.668620 0.071 Uiso 1 1 calc R U . . .
C15 C 0.0166(10) 0.6342(4) 0.6661(3) 0.0536(15) Uani 1 1 d . . . . .
H15 H -0.089891 0.625789 0.642281 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3601(7) 0.4933(3) 0.7368(3) 0.0377(11) Uani 1 1 d . . . . .
C17 C 0.5478(7) 0.4946(3) 0.7069(3) 0.0399(11) Uani 1 1 d . . . . .
C18 C 0.3921(8) 0.4749(4) 0.8178(3) 0.0410(12) Uani 1 1 d . . . . .
C19 C 0.2854(10) 0.4738(4) 0.8799(3) 0.0536(15) Uani 1 1 d . . . . .
H19 H 0.168284 0.488927 0.875885 0.064 Uiso 1 1 calc R U . . .
C20 C 0.3539(13) 0.4501(5) 0.9473(4) 0.071(2) Uani 1 1 d . . . . .
H20 H 0.282299 0.448988 0.989167 0.085 Uiso 1 1 calc R U . . .
C21 C 0.5234(13) 0.4285(5) 0.9540(4) 0.070(2) Uani 1 1 d . . . . .
H21 H 0.566354 0.412921 1.000596 0.085 Uiso 1 1 calc R U . . .
C22 C 0.6345(12) 0.4287(4) 0.8941(4) 0.0646(19) Uani 1 1 d . . . . .
H22 H 0.751322 0.413384 0.898872 0.078 Uiso 1 1 calc R U . . .
C23 C 0.5658(8) 0.4523(3) 0.8273(3) 0.0427(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.886(7) . ?
N1 C11 1.335(8) . ?
N1 C15 1.353(8) . ?
O1 C10 1.346(7) . ?
O1 C7 1.438(7) . ?
C1 C3 1.377(9) . ?
C1 C2 1.407(11) . ?
C1 H1 0.9400 . ?
C2 C4 1.375(12) . ?
C2 H2 0.9400 . ?
O2 C10 1.211(7) . ?
N2 C17 1.355(7) . ?
N2 C23 1.405(8) . ?
N2 H2A 0.8700 . ?
C3 C6 1.386(9) . ?
C3 H3 0.9400 . ?
O3 C17 1.239(7) . ?
C4 C5 1.387(10) . ?
C4 H4 0.9400 . ?
C5 C6 1.387(9) . ?
C5 H5 0.9400 . ?
C6 C7 1.514(8) . ?
C7 C8 1.520(8) . ?
C7 H7 0.9900 . ?
C8 C9 1.522(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.517(7) . ?
C9 C16 1.553(7) . ?
C9 H9 0.9900 . ?
C11 C12 1.410(8) . ?
C11 C16 1.525(7) . ?
C12 C13 1.383(9) . ?
C13 C14 1.378(11) . ?
C13 H13 0.9400 . ?
C14 C15 1.383(9) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 C18 1.516(8) . ?
C16 C17 1.552(7) . ?
C18 C19 1.396(9) . ?
C18 C23 1.401(9) . ?
C19 C20 1.382(10) . ?
C19 H19 0.9400 . ?
C20 C21 1.362(13) . ?
C20 H20 0.9400 . ?
C21 C22 1.385(12) . ?
C21 H21 0.9400 . ?
C22 C23 1.372(9) . ?
C22 H22 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C15 120.0(5) . . ?
C10 O1 C7 111.3(4) . . ?
C3 C1 C2 120.3(7) . . ?
C3 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C4 C2 C1 118.3(6) . . ?
C4 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C17 N2 C23 111.8(5) . . ?
C17 N2 H2A 124.1 . . ?
C23 N2 H2A 124.1 . . ?
C1 C3 C6 121.2(6) . . ?
C1 C3 H3 119.4 . . ?
C6 C3 H3 119.4 . . ?
C2 C4 C5 121.3(7) . . ?
C2 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.4(7) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C3 C6 C5 118.6(6) . . ?
C3 C6 C7 122.2(5) . . ?
C5 C6 C7 119.1(6) . . ?
O1 C7 C6 109.6(5) . . ?
O1 C7 C8 107.2(4) . . ?
C6 C7 C8 114.2(5) . . ?
O1 C7 H7 108.6 . . ?
C6 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C7 C8 C9 104.2(5) . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C8 103.8(5) . . ?
C10 C9 C16 114.1(4) . . ?
C8 C9 C16 117.9(5) . . ?
C10 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C16 C9 H9 106.8 . . ?
O2 C10 O1 120.9(5) . . ?
O2 C10 C9 128.7(5) . . ?
O1 C10 C9 110.3(4) . . ?
N1 C11 C12 120.3(5) . . ?
N1 C11 C16 115.2(5) . . ?
C12 C11 C16 124.4(5) . . ?
C13 C12 C11 119.3(6) . . ?
C13 C12 Br1 119.2(5) . . ?
C11 C12 Br1 121.4(4) . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.7(6) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.0(6) . . ?
N1 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C18 C16 C11 116.2(4) . . ?
C18 C16 C17 100.8(5) . . ?
C11 C16 C17 112.2(4) . . ?
C18 C16 C9 111.5(5) . . ?
C11 C16 C9 110.3(4) . . ?
C17 C16 C9 105.0(4) . . ?
O3 C17 N2 125.5(5) . . ?
O3 C17 C16 126.6(5) . . ?
N2 C17 C16 107.8(4) . . ?
C19 C18 C23 117.8(6) . . ?
C19 C18 C16 133.3(6) . . ?
C23 C18 C16 108.9(5) . . ?
C20 C19 C18 119.2(8) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 121.0(7) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.9(7) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 116.8(8) . . ?
C23 C22 H22 121.6 . . ?
C21 C22 H22 121.6 . . ?
C22 C23 C18 123.3(7) . . ?
C22 C23 N2 127.8(7) . . ?
C18 C23 N2 108.9(5) . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.190




####################################################################### 
# 
# 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_zhd009
_database_code_depnum_ccdc_archive 'CCDC 1992675'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Br N2 O4'
_chemical_formula_sum            'C27 H25 Br N2 O4'
_chemical_formula_weight         521.40

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      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                   9.4091(4)
_cell_length_b                   11.5174(4)
_cell_length_c                   22.8668(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.9960(10)
_cell_angle_gamma                90
_cell_volume                     2476.53(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    169(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    1.695
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      169(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35612
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.511
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5071
_reflns_number_gt                4302
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0239P)²+3.1261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5071
_refine_ls_number_parameters     314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
Br Br 0.84507(3) 0.28805(2) 0.61935(2) 0.03105(9) Uani 1 1 d . . . . .
O1 O 0.30966(16) 0.55911(14) 0.60242(7) 0.0241(3) Uani 1 1 d . . . . .
O2 O 0.42724(17) 0.48709(15) 0.68187(7) 0.0264(4) Uani 1 1 d . . . . .
O3 O 0.3892(2) 0.81747(16) 0.64689(8) 0.0351(4) Uani 1 1 d . . . . .
O4 O 0.54746(17) 0.39997(13) 0.56120(7) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.7081(2) 0.55489(17) 0.72404(8) 0.0260(4) Uani 1 1 d . . . . .
N2 N 0.7290(2) 0.50319(16) 0.52081(8) 0.0200(4) Uani 1 1 d D . . . .
H2N H 0.721(3) 0.481(2) 0.4856(8) 0.026(7) Uiso 1 1 d D . . . .
C1 C 0.4146(2) 0.55274(19) 0.63456(9) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.5489(2) 0.62537(18) 0.62682(9) 0.0170(4) Uani 1 1 d . . . . .
H2 H 0.565894 0.670651 0.663718 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5224(2) 0.71295(18) 0.57751(9) 0.0185(4) Uani 1 1 d . . . . .
H3A H 0.613513 0.749313 0.567240 0.022 Uiso 1 1 calc R U . . .
H3B H 0.482979 0.672349 0.542395 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4191(2) 0.80634(19) 0.59588(10) 0.0226(5) Uani 1 1 d . . . . .
C5 C 0.3115(3) 0.4091(3) 0.70038(12) 0.0375(6) Uani 1 1 d . . . . .
C6 C 0.1840(3) 0.4805(3) 0.71620(17) 0.0617(10) Uani 1 1 d . . . . .
H6A H 0.139563 0.513764 0.680588 0.093 Uiso 1 1 calc R U . . .
H6B H 0.214332 0.543259 0.742748 0.093 Uiso 1 1 calc R U . . .
H6C H 0.115175 0.430920 0.735522 0.093 Uiso 1 1 calc R U . . .
C7 C 0.3809(4) 0.3519(3) 0.75436(14) 0.0567(10) Uani 1 1 d . . . . .
H7A H 0.410310 0.411913 0.782679 0.085 Uiso 1 1 calc R U . . .
H7B H 0.464440 0.307625 0.742917 0.085 Uiso 1 1 calc R U . . .
H7C H 0.312699 0.299537 0.772169 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2796(4) 0.3195(3) 0.65334(15) 0.0578(9) Uani 1 1 d . . . . .
H8A H 0.233306 0.357241 0.619317 0.087 Uiso 1 1 calc R U . . .
H8B H 0.216264 0.259928 0.668534 0.087 Uiso 1 1 calc R U . . .
H8C H 0.368489 0.283241 0.641708 0.087 Uiso 1 1 calc R U . . .
C11 C 0.7265(2) 0.48813(19) 0.67704(9) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.7919(2) 0.38030(19) 0.68355(10) 0.0215(5) Uani 1 1 d . . . . .
C13 C 0.8290(3) 0.3384(2) 0.73906(10) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.871457 0.263994 0.743873 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8031(3) 0.4066(2) 0.78673(10) 0.0297(5) Uani 1 1 d . . . . .
H14 H 0.824034 0.379701 0.825359 0.036 Uiso 1 1 calc R U . . .
C15 C 0.7451(3) 0.5167(2) 0.77669(11) 0.0318(6) Uani 1 1 d . . . . .
H15 H 0.731642 0.566242 0.809261 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6443(2) 0.46970(18) 0.56479(9) 0.0175(4) Uani 1 1 d . . . . .
C22 C 0.6832(2) 0.54668(18) 0.61863(9) 0.0168(4) Uani 1 1 d . . . . .
C23 C 0.8100(2) 0.61433(18) 0.59745(9) 0.0165(4) Uani 1 1 d . . . . .
C24 C 0.9025(2) 0.68960(18) 0.62656(10) 0.0204(5) Uani 1 1 d . . . . .
H24 H 0.891346 0.707709 0.666675 0.024 Uiso 1 1 calc R U . . .
C25 C 1.0130(2) 0.7383(2) 0.59540(10) 0.0242(5) Uani 1 1 d . . . . .
H25 H 1.077686 0.790369 0.614520 0.029 Uiso 1 1 calc R U . . .
C26 C 1.0290(2) 0.7115(2) 0.53683(11) 0.0261(5) Uani 1 1 d . . . . .
H26 H 1.103898 0.746453 0.516243 0.031 Uiso 1 1 calc R U . . .
C27 C 0.9377(2) 0.6347(2) 0.50787(10) 0.0228(5) Uani 1 1 d . . . . .
H27 H 0.949345 0.615964 0.467860 0.027 Uiso 1 1 calc R U . . .
C28 C 0.8297(2) 0.58637(18) 0.53876(9) 0.0182(4) Uani 1 1 d . . . . .
C31 C 0.3577(2) 0.88680(19) 0.55025(11) 0.0256(5) Uani 1 1 d . . . . .
C32 C 0.3834(3) 0.8752(2) 0.49141(11) 0.0301(6) Uani 1 1 d . . . . .
H32 H 0.442819 0.814457 0.478353 0.036 Uiso 1 1 calc R U . . .
C33 C 0.3218(3) 0.9528(2) 0.45133(14) 0.0423(7) Uani 1 1 d . . . . .
H33 H 0.340663 0.945829 0.410936 0.051 Uiso 1 1 calc R U . . .
C34 C 0.2339(3) 1.0397(3) 0.46997(17) 0.0522(9) Uani 1 1 d . . . . .
H34 H 0.190443 1.091233 0.442283 0.063 Uiso 1 1 calc R U . . .
C35 C 0.2085(3) 1.0522(3) 0.52849(18) 0.0578(10) Uani 1 1 d . . . . .
H35 H 0.148228 1.112755 0.541078 0.069 Uiso 1 1 calc R U . . .
C36 C 0.2702(3) 0.9770(2) 0.56908(15) 0.0415(7) Uani 1 1 d . . . . .
H36 H 0.253501 0.986443 0.609532 0.050 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
Br C12 1.894(2) . ?
O1 C1 1.213(3) . ?
O2 C1 1.322(3) . ?
O2 C5 1.485(3) . ?
O3 C4 1.216(3) . ?
O4 C21 1.215(3) . ?
N1 C15 1.317(3) . ?
N1 C11 1.338(3) . ?
N2 C21 1.360(3) . ?
N2 C28 1.399(3) . ?
C1 C2 1.530(3) . ?
C2 C3 1.527(3) . ?
C2 C22 1.571(3) . ?
C3 C4 1.518(3) . ?
C4 C31 1.496(3) . ?
C5 C6 1.509(4) . ?
C5 C8 1.513(4) . ?
C5 C7 1.526(4) . ?
C11 C12 1.392(3) . ?
C11 C22 1.538(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.397(4) . ?
C21 C22 1.551(3) . ?
C22 C23 1.519(3) . ?
C23 C24 1.383(3) . ?
C23 C28 1.399(3) . ?
C24 C25 1.398(3) . ?
C25 C26 1.388(3) . ?
C26 C27 1.386(3) . ?
C27 C28 1.375(3) . ?
C31 C32 1.382(4) . ?
C31 C36 1.403(3) . ?
C32 C33 1.392(3) . ?
C33 C34 1.375(5) . ?
C34 C35 1.375(5) . ?
C35 C36 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C5 122.26(18) . . ?
C15 N1 C11 120.4(2) . . ?
C21 N2 C28 112.67(18) . . ?
O1 C1 O2 125.3(2) . . ?
O1 C1 C2 123.7(2) . . ?
O2 C1 C2 110.89(18) . . ?
C3 C2 C1 109.39(17) . . ?
C3 C2 C22 113.86(17) . . ?
C1 C2 C22 111.64(17) . . ?
C4 C3 C2 110.69(18) . . ?
O3 C4 C31 120.5(2) . . ?
O3 C4 C3 120.8(2) . . ?
C31 C4 C3 118.7(2) . . ?
O2 C5 C6 109.6(2) . . ?
O2 C5 C8 109.8(2) . . ?
C6 C5 C8 113.7(3) . . ?
O2 C5 C7 101.2(2) . . ?
C6 C5 C7 111.3(3) . . ?
C8 C5 C7 110.5(3) . . ?
N1 C11 C12 119.7(2) . . ?
N1 C11 C22 114.07(18) . . ?
C12 C11 C22 125.9(2) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 Br 116.62(17) . . ?
C11 C12 Br 123.06(17) . . ?
C14 C13 C12 118.7(2) . . ?
C13 C14 C15 117.9(2) . . ?
N1 C15 C14 122.9(2) . . ?
O4 C21 N2 126.5(2) . . ?
O4 C21 C22 125.9(2) . . ?
N2 C21 C22 107.27(18) . . ?
C23 C22 C11 108.33(17) . . ?
C23 C22 C21 101.90(17) . . ?
C11 C22 C21 119.12(17) . . ?
C23 C22 C2 112.71(16) . . ?
C11 C22 C2 109.82(17) . . ?
C21 C22 C2 104.85(16) . . ?
C24 C23 C28 120.3(2) . . ?
C24 C23 C22 131.1(2) . . ?
C28 C23 C22 108.65(18) . . ?
C23 C24 C25 118.2(2) . . ?
C26 C25 C24 120.7(2) . . ?
C27 C26 C25 121.1(2) . . ?
C28 C27 C26 118.0(2) . . ?
C27 C28 N2 129.2(2) . . ?
C27 C28 C23 121.6(2) . . ?
N2 C28 C23 109.16(19) . . ?
C32 C31 C36 119.7(2) . . ?
C32 C31 C4 122.9(2) . . ?
C36 C31 C4 117.5(2) . . ?
C31 C32 C33 119.7(3) . . ?
C34 C33 C32 120.3(3) . . ?
C33 C34 C35 120.3(3) . . ?
C34 C35 C36 120.3(3) . . ?
C35 C36 C31 119.7(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
C5 O2 C1 O1 1.8(4) . . . . ?
C5 O2 C1 C2 179.0(2) . . . . ?
O1 C1 C2 C3 5.9(3) . . . . ?
O2 C1 C2 C3 -171.48(18) . . . . ?
O1 C1 C2 C22 -121.1(2) . . . . ?
O2 C1 C2 C22 61.6(2) . . . . ?
C1 C2 C3 C4 70.1(2) . . . . ?
C22 C2 C3 C4 -164.26(17) . . . . ?
C2 C3 C4 O3 13.3(3) . . . . ?
C2 C3 C4 C31 -168.35(18) . . . . ?
C1 O2 C5 C6 -64.4(3) . . . . ?
C1 O2 C5 C8 61.2(3) . . . . ?
C1 O2 C5 C7 178.0(2) . . . . ?
C15 N1 C11 C12 -3.5(3) . . . . ?
C15 N1 C11 C22 -177.9(2) . . . . ?
N1 C11 C12 C13 4.6(3) . . . . ?
C22 C11 C12 C13 178.3(2) . . . . ?
N1 C11 C12 Br -171.60(17) . . . . ?
C22 C11 C12 Br 2.1(3) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
Br C12 C13 C14 174.77(19) . . . . ?
C12 C13 C14 C15 -2.2(4) . . . . ?
C11 N1 C15 C14 -0.6(4) . . . . ?
C13 C14 C15 N1 3.4(4) . . . . ?
C28 N2 C21 O4 179.1(2) . . . . ?
C28 N2 C21 C22 5.2(2) . . . . ?
N1 C11 C22 C23 87.2(2) . . . . ?
C12 C11 C22 C23 -86.8(2) . . . . ?
N1 C11 C22 C21 -157.12(19) . . . . ?
C12 C11 C22 C21 28.8(3) . . . . ?
N1 C11 C22 C2 -36.3(2) . . . . ?
C12 C11 C22 C2 149.7(2) . . . . ?
O4 C21 C22 C23 -179.8(2) . . . . ?
N2 C21 C22 C23 -5.9(2) . . . . ?
O4 C21 C22 C11 61.1(3) . . . . ?
N2 C21 C22 C11 -124.9(2) . . . . ?
O4 C21 C22 C2 -62.2(3) . . . . ?
N2 C21 C22 C2 111.78(18) . . . . ?
C3 C2 C22 C23 42.6(2) . . . . ?
C1 C2 C22 C23 167.13(17) . . . . ?
C3 C2 C22 C11 163.54(17) . . . . ?
C1 C2 C22 C11 -72.0(2) . . . . ?
C3 C2 C22 C21 -67.4(2) . . . . ?
C1 C2 C22 C21 57.1(2) . . . . ?
C11 C22 C23 C24 -46.5(3) . . . . ?
C21 C22 C23 C24 -172.9(2) . . . . ?
C2 C22 C23 C24 75.2(3) . . . . ?
C11 C22 C23 C28 131.12(18) . . . . ?
C21 C22 C23 C28 4.7(2) . . . . ?
C2 C22 C23 C28 -107.14(19) . . . . ?
C28 C23 C24 C25 1.5(3) . . . . ?
C22 C23 C24 C25 178.9(2) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C25 C26 C27 C28 0.5(3) . . . . ?
C26 C27 C28 N2 -176.5(2) . . . . ?
C26 C27 C28 C23 0.9(3) . . . . ?
C21 N2 C28 C27 175.5(2) . . . . ?
C21 N2 C28 C23 -2.1(2) . . . . ?
C24 C23 C28 C27 -1.9(3) . . . . ?
C22 C23 C28 C27 -179.85(19) . . . . ?
C24 C23 C28 N2 175.92(19) . . . . ?
C22 C23 C28 N2 -2.0(2) . . . . ?
O3 C4 C31 C32 -177.3(2) . . . . ?
C3 C4 C31 C32 4.4(3) . . . . ?
O3 C4 C31 C36 2.5(3) . . . . ?
C3 C4 C31 C36 -175.8(2) . . . . ?
C36 C31 C32 C33 -0.2(4) . . . . ?
C4 C31 C32 C33 179.5(2) . . . . ?
C31 C32 C33 C34 -1.1(4) . . . . ?
C32 C33 C34 C35 1.5(4) . . . . ?
C33 C34 C35 C36 -0.5(5) . . . . ?
C34 C35 C36 C31 -0.8(5) . . . . ?
C32 C31 C36 C35 1.2(4) . . . . ?
C4 C31 C36 C35 -178.6(3) . . . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.067



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA, Hexane'
####################################################################### 
# 
# 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_zhd019
_database_code_depnum_ccdc_archive 'CCDC 2009353'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 Br N2 O4'
_chemical_formula_sum            'C27 H25 Br N2 O4'
_chemical_formula_weight         521.40

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.2371(4)
_cell_length_b                   16.5924(5)
_cell_length_c                   11.5023(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.3160(10)
_cell_angle_gamma                90
_cell_volume                     2424.57(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9778
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      72.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    2.608
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7382
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44480
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         72.401
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4773
_reflns_number_gt                4508
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0399P)²+2.6960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4773
_refine_ls_number_parameters     314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Br Br 0.05536(2) 0.29937(2) 0.27228(3) 0.05465(12) Uani 1 1 d . . . . .
O1 O 0.48339(15) 0.34239(12) 0.2192(2) 0.0584(6) Uani 1 1 d . . . . .
O2 O 0.37623(12) 0.61793(10) 0.32507(15) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.24817(11) 0.61142(8) 0.14712(13) 0.0289(3) Uani 1 1 d . . . . .
O4 O 0.12488(11) 0.43551(9) 0.03347(12) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.04895(13) 0.50423(11) 0.16101(15) 0.0274(4) Uani 1 1 d D . . . .
H1N H -0.0065(17) 0.5224(16) 0.109(2) 0.039(7) Uiso 1 1 d D . . . .
N2 N 0.36336(15) 0.38142(12) 0.36265(18) 0.0386(5) Uani 1 1 d . . . . .
C1 C 0.48860(18) 0.41344(15) 0.2454(2) 0.0404(6) Uani 1 1 d . . . . .
C2 C 0.41302(16) 0.44557(14) 0.3154(2) 0.0326(5) Uani 1 1 d . . . . .
H2 H 0.451223 0.482391 0.382161 0.039 Uiso 1 1 calc R U . . .
C3 C 0.31926(15) 0.49013(12) 0.22744(18) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.319558 0.477231 0.142609 0.032 Uiso 1 1 calc R U . . .
C4 C 0.21779(15) 0.45270(12) 0.24962(17) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.12583(15) 0.46123(12) 0.13343(17) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.32022(15) 0.58086(13) 0.24125(19) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.22937(18) 0.69953(13) 0.1302(2) 0.0335(5) Uani 1 1 d . . . . .
C8 C 0.2063(2) 0.73594(16) 0.2408(3) 0.0451(6) Uani 1 1 d . . . . .
H8A H 0.270669 0.736264 0.308505 0.068 Uiso 1 1 calc R U . . .
H8B H 0.152230 0.703823 0.262745 0.068 Uiso 1 1 calc R U . . .
H8C H 0.180897 0.791301 0.222705 0.068 Uiso 1 1 calc R U . . .
C9 C 0.3243(2) 0.73739(16) 0.1029(3) 0.0471(6) Uani 1 1 d . . . . .
H9A H 0.385417 0.733102 0.174267 0.071 Uiso 1 1 calc R U . . .
H9B H 0.309820 0.794320 0.082093 0.071 Uiso 1 1 calc R U . . .
H9C H 0.339125 0.709246 0.034564 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1335(2) 0.70151(15) 0.0208(3) 0.0463(6) Uani 1 1 d . . . . .
H10A H 0.148374 0.671591 -0.045959 0.069 Uiso 1 1 calc R U . . .
H10B H 0.116343 0.757531 -0.003996 0.069 Uiso 1 1 calc R U . . .
H10C H 0.073649 0.676688 0.041650 0.069 Uiso 1 1 calc R U . . .
C11 C 0.56376(18) 0.46812(16) 0.2107(2) 0.0402(5) Uani 1 1 d . . . . .
C12 C 0.5771(2) 0.54830(18) 0.2457(2) 0.0460(6) Uani 1 1 d . . . . .
H12 H 0.536961 0.570520 0.294540 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6489(2) 0.5963(2) 0.2097(3) 0.0578(7) Uani 1 1 d . . . . .
H13 H 0.657352 0.651276 0.233681 0.069 Uiso 1 1 calc R U . . .
C14 C 0.7080(3) 0.5645(2) 0.1391(3) 0.0610(8) Uani 1 1 d . . . . .
H14 H 0.756265 0.597632 0.113591 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6968(3) 0.4849(2) 0.1060(3) 0.0606(8) Uani 1 1 d . . . . .
H15 H 0.739035 0.462696 0.059557 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6250(2) 0.4370(2) 0.1394(2) 0.0528(7) Uani 1 1 d . . . . .
H16 H 0.616769 0.382307 0.113963 0.063 Uiso 1 1 calc R U . . .
C21 C 0.17631(16) 0.49559(12) 0.34172(18) 0.0270(4) Uani 1 1 d . . . . .
C22 C 0.21867(18) 0.50770(14) 0.46512(19) 0.0341(5) Uani 1 1 d . . . . .
H22 H 0.286394 0.487280 0.505963 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1604(2) 0.55021(15) 0.5280(2) 0.0404(5) Uani 1 1 d . . . . .
H23 H 0.188634 0.559034 0.612542 0.049 Uiso 1 1 calc R U . . .
C24 C 0.0615(2) 0.57987(15) 0.4688(2) 0.0402(5) Uani 1 1 d . . . . .
H24 H 0.022973 0.608718 0.513603 0.048 Uiso 1 1 calc R U . . .
C25 C 0.01735(18) 0.56828(14) 0.3449(2) 0.0343(5) Uani 1 1 d . . . . .
H25 H -0.050288 0.588852 0.304073 0.041 Uiso 1 1 calc R U . . .
C26 C 0.07629(16) 0.52557(13) 0.28422(18) 0.0276(4) Uani 1 1 d . . . . .
C31 C 0.25751(16) 0.36530(13) 0.28413(19) 0.0309(4) Uani 1 1 d . . . . .
H31 H 0.262734 0.336218 0.209894 0.037 Uiso 1 1 calc R U . . .
C32 C 0.2005(2) 0.31376(14) 0.3512(2) 0.0392(5) Uani 1 1 d . . . . .
C33 C 0.2472(3) 0.27418(16) 0.4523(3) 0.0514(7) Uani 1 1 d . . . . .
H33 H 0.206927 0.240102 0.488569 0.062 Uiso 1 1 calc R U . . .
C34 C 0.3590(3) 0.28279(18) 0.5073(3) 0.0581(8) Uani 1 1 d . . . . .
H34 H 0.393952 0.251066 0.575504 0.070 Uiso 1 1 calc R U . . .
C35 C 0.4122(2) 0.33587(15) 0.4609(2) 0.0460(6) Uani 1 1 d . . . . .
H35 H 0.485640 0.342156 0.496922 0.055 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
Br C32 1.896(3) . ?
O1 C1 1.214(3) . ?
O2 C6 1.207(3) . ?
O3 C6 1.326(3) . ?
O3 C7 1.486(2) . ?
O4 C5 1.223(2) . ?
N1 C5 1.352(3) . ?
N1 C26 1.406(3) . ?
N2 C35 1.362(3) . ?
N2 C2 1.435(3) . ?
N2 C31 1.463(3) . ?
C1 C11 1.481(4) . ?
C1 C2 1.545(3) . ?
C2 C3 1.551(3) . ?
C3 C6 1.514(3) . ?
C3 C4 1.564(3) . ?
C4 C21 1.502(3) . ?
C4 C5 1.541(2) . ?
C4 C31 1.555(3) . ?
C7 C8 1.515(3) . ?
C7 C9 1.515(3) . ?
C7 C10 1.516(3) . ?
C11 C12 1.387(4) . ?
C11 C16 1.404(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.371(5) . ?
C15 C16 1.373(5) . ?
C21 C22 1.386(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.389(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.393(3) . ?
C25 C26 1.380(3) . ?
C31 C32 1.491(3) . ?
C32 C33 1.327(4) . ?
C33 C34 1.444(5) . ?
C34 C35 1.330(5) . ?

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 O3 C7 122.57(16) . . ?
C5 N1 C26 111.83(16) . . ?
C35 N2 C2 124.4(2) . . ?
C35 N2 C31 124.0(2) . . ?
C2 N2 C31 111.29(17) . . ?
O1 C1 C11 121.6(2) . . ?
O1 C1 C2 117.7(3) . . ?
C11 C1 C2 120.8(2) . . ?
N2 C2 C1 111.96(19) . . ?
N2 C2 C3 103.47(17) . . ?
C1 C2 C3 109.92(18) . . ?
C6 C3 C2 115.09(17) . . ?
C6 C3 C4 111.10(16) . . ?
C2 C3 C4 105.70(17) . . ?
C21 C4 C5 102.23(16) . . ?
C21 C4 C31 115.21(17) . . ?
C5 C4 C31 115.79(16) . . ?
C21 C4 C3 115.31(16) . . ?
C5 C4 C3 109.11(16) . . ?
C31 C4 C3 99.65(16) . . ?
O4 C5 N1 126.54(17) . . ?
O4 C5 C4 125.47(18) . . ?
N1 C5 C4 107.96(16) . . ?
O2 C6 O3 126.7(2) . . ?
O2 C6 C3 125.17(19) . . ?
O3 C6 C3 108.17(16) . . ?
O3 C7 C8 110.39(19) . . ?
O3 C7 C9 108.47(19) . . ?
C8 C7 C9 112.6(2) . . ?
O3 C7 C10 101.55(17) . . ?
C8 C7 C10 111.6(2) . . ?
C9 C7 C10 111.6(2) . . ?
C12 C11 C16 118.4(3) . . ?
C12 C11 C1 123.4(2) . . ?
C16 C11 C1 118.3(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 120.2(3) . . ?
C15 C14 C13 119.8(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C11 120.6(3) . . ?
C22 C21 C26 119.4(2) . . ?
C22 C21 C4 131.9(2) . . ?
C26 C21 C4 108.71(17) . . ?
C21 C22 C23 118.9(2) . . ?
C24 C23 C22 120.7(2) . . ?
C23 C24 C25 121.4(2) . . ?
C26 C25 C24 117.0(2) . . ?
C25 C26 C21 122.6(2) . . ?
C25 C26 N1 128.1(2) . . ?
C21 C26 N1 109.24(18) . . ?
N2 C31 C32 108.76(18) . . ?
N2 C31 C4 100.58(16) . . ?
C32 C31 C4 118.88(19) . . ?
C33 C32 C31 124.0(2) . . ?
C33 C32 Br 121.1(2) . . ?
C31 C32 Br 114.62(16) . . ?
C32 C33 C34 120.1(3) . . ?
C35 C34 C33 118.9(2) . . ?
C34 C35 N2 121.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C35 N2 C2 C1 75.2(3) . . . . ?
C31 N2 C2 C1 -98.5(2) . . . . ?
C35 N2 C2 C3 -166.5(2) . . . . ?
C31 N2 C2 C3 19.8(2) . . . . ?
O1 C1 C2 N2 13.1(3) . . . . ?
C11 C1 C2 N2 -167.53(19) . . . . ?
O1 C1 C2 C3 -101.3(2) . . . . ?
C11 C1 C2 C3 78.1(2) . . . . ?
N2 C2 C3 C6 132.09(19) . . . . ?
C1 C2 C3 C6 -108.2(2) . . . . ?
N2 C2 C3 C4 9.1(2) . . . . ?
C1 C2 C3 C4 128.81(19) . . . . ?
C6 C3 C4 C21 -33.3(2) . . . . ?
C2 C3 C4 C21 92.23(19) . . . . ?
C6 C3 C4 C5 81.1(2) . . . . ?
C2 C3 C4 C5 -153.44(16) . . . . ?
C6 C3 C4 C31 -157.21(16) . . . . ?
C2 C3 C4 C31 -31.71(19) . . . . ?
C26 N1 C5 O4 -178.9(2) . . . . ?
C26 N1 C5 C4 -1.0(2) . . . . ?
C21 C4 C5 O4 179.3(2) . . . . ?
C31 C4 C5 O4 -54.6(3) . . . . ?
C3 C4 C5 O4 56.7(3) . . . . ?
C21 C4 C5 N1 1.4(2) . . . . ?
C31 C4 C5 N1 127.45(19) . . . . ?
C3 C4 C5 N1 -121.18(18) . . . . ?
C7 O3 C6 O2 2.4(3) . . . . ?
C7 O3 C6 C3 -178.71(17) . . . . ?
C2 C3 C6 O2 -12.7(3) . . . . ?
C4 C3 C6 O2 107.4(2) . . . . ?
C2 C3 C6 O3 168.40(18) . . . . ?
C4 C3 C6 O3 -71.5(2) . . . . ?
C6 O3 C7 C8 -55.1(3) . . . . ?
C6 O3 C7 C9 68.7(3) . . . . ?
C6 O3 C7 C10 -173.6(2) . . . . ?
O1 C1 C11 C12 -175.6(2) . . . . ?
C2 C1 C11 C12 5.1(3) . . . . ?
O1 C1 C11 C16 4.0(3) . . . . ?
C2 C1 C11 C16 -175.3(2) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C1 C11 C12 C13 -179.8(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 C16 1.9(5) . . . . ?
C14 C15 C16 C11 -1.7(4) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
C1 C11 C16 C15 -179.2(2) . . . . ?
C5 C4 C21 C22 177.8(2) . . . . ?
C31 C4 C21 C22 51.3(3) . . . . ?
C3 C4 C21 C22 -64.0(3) . . . . ?
C5 C4 C21 C26 -1.3(2) . . . . ?
C31 C4 C21 C26 -127.74(18) . . . . ?
C3 C4 C21 C26 116.94(18) . . . . ?
C26 C21 C22 C23 -0.6(3) . . . . ?
C4 C21 C22 C23 -179.6(2) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C21 -0.8(3) . . . . ?
C24 C25 C26 N1 178.4(2) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C4 C21 C26 C25 -179.86(19) . . . . ?
C22 C21 C26 N1 -178.39(19) . . . . ?
C4 C21 C26 N1 0.8(2) . . . . ?
C5 N1 C26 C25 -179.2(2) . . . . ?
C5 N1 C26 C21 0.1(2) . . . . ?
C35 N2 C31 C32 20.2(3) . . . . ?
C2 N2 C31 C32 -166.10(19) . . . . ?
C35 N2 C31 C4 145.8(2) . . . . ?
C2 N2 C31 C4 -40.5(2) . . . . ?
C21 C4 C31 N2 -82.0(2) . . . . ?
C5 C4 C31 N2 158.81(18) . . . . ?
C3 C4 C31 N2 42.01(19) . . . . ?
C21 C4 C31 C32 36.5(3) . . . . ?
C5 C4 C31 C32 -82.7(2) . . . . ?
C3 C4 C31 C32 160.47(18) . . . . ?
N2 C31 C32 C33 -14.7(3) . . . . ?
C4 C31 C32 C33 -128.9(3) . . . . ?
N2 C31 C32 Br 171.38(15) . . . . ?
C4 C31 C32 Br 57.3(2) . . . . ?
C31 C32 C33 C34 3.2(4) . . . . ?
Br C32 C33 C34 176.7(2) . . . . ?
C32 C33 C34 C35 5.6(5) . . . . ?
C33 C34 C35 N2 -0.4(4) . . . . ?
C2 N2 C35 C34 173.2(3) . . . . ?
C31 N2 C35 C34 -13.9(4) . . . . ?

_refine_diff_density_max         1.302
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.058



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc, PE'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_zhd020
_database_code_depnum_ccdc_archive 'CCDC 2010306'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2020-06-17 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 Br N2 O4'
_chemical_formula_sum            'C27 H27 Br N2 O4'
_chemical_formula_weight         523.41

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

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

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

_cell_length_a                   21.8518(7)
_cell_length_b                   10.5122(3)
_cell_length_c                   22.7425(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.208(2)
_cell_angle_gamma                90
_cell_volume                     4962.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.692
_shelx_estimated_absorpt_T_min   0.506
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_T_max  0.9046
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67568
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5714
_reflns_number_gt                4274
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0190P)²+17.5482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5714
_refine_ls_number_parameters     360
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.569
_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
Br Br 0.20142(2) 0.51541(3) 0.63864(2) 0.03925(11) Uani 1 1 d . . . . .
O1 O 0.43707(10) 0.70180(19) 0.59392(10) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.41858(15) 0.6145(3) 0.50004(11) 0.0618(8) Uani 1 1 d . . . . .
O3 O 0.26601(10) 0.58083(18) 0.49801(9) 0.0294(5) Uani 1 1 d . . . . .
N1 N 0.32526(12) 0.2831(2) 0.58182(12) 0.0303(6) Uani 1 1 d D . . . .
N2 N 0.29100(11) 0.7181(2) 0.58071(11) 0.0242(5) Uani 1 1 d D . . . .
H2N H 0.2710(15) 0.785(2) 0.5602(14) 0.037(9) Uiso 1 1 d D . . . .
C1 C 0.46052(15) 0.8256(3) 0.57779(16) 0.0403(8) Uani 1 1 d D . . . .
C2A C 0.4797(5) 0.8925(9) 0.6418(4) 0.0443(8) Uani 0.529(15) 1 d D . P A 1
H2AA H 0.509591 0.838076 0.672762 0.066 Uiso 0.529(15) 1 calc R U P A 1
H2AB H 0.441050 0.907671 0.653937 0.066 Uiso 0.529(15) 1 calc R U P A 1
H2AC H 0.500633 0.973810 0.639276 0.066 Uiso 0.529(15) 1 calc R U P A 1
C3A C 0.4074(4) 0.9007(9) 0.5319(5) 0.0443(8) Uani 0.529(15) 1 d D . P A 1
H3AA H 0.368544 0.899057 0.544693 0.066 Uiso 0.529(15) 1 calc R U P A 1
H3AB H 0.397880 0.862582 0.490648 0.066 Uiso 0.529(15) 1 calc R U P A 1
H3AC H 0.421404 0.988915 0.530584 0.066 Uiso 0.529(15) 1 calc R U P A 1
C4A C 0.5249(5) 0.7917(9) 0.5657(6) 0.0443(8) Uani 0.529(15) 1 d D . P A 1
H4AA H 0.554036 0.750466 0.602480 0.066 Uiso 0.529(15) 1 calc R U P A 1
H4AB H 0.544946 0.869631 0.556754 0.066 Uiso 0.529(15) 1 calc R U P A 1
H4AC H 0.516173 0.733753 0.530304 0.066 Uiso 0.529(15) 1 calc R U P A 1
C2B C 0.4608(5) 0.9095(9) 0.6303(5) 0.0443(8) Uani 0.471(15) 1 d D . P A 2
H2BA H 0.486933 0.870661 0.669220 0.066 Uiso 0.471(15) 1 calc R U P A 2
H2BB H 0.416549 0.920897 0.631195 0.066 Uiso 0.471(15) 1 calc R U P A 2
H2BC H 0.478986 0.992447 0.625240 0.066 Uiso 0.471(15) 1 calc R U P A 2
C3B C 0.4130(5) 0.8716(10) 0.5148(5) 0.0443(8) Uani 0.471(15) 1 d D . P A 2
H3BA H 0.368775 0.868577 0.516676 0.066 Uiso 0.471(15) 1 calc R U P A 2
H3BB H 0.416611 0.816003 0.481492 0.066 Uiso 0.471(15) 1 calc R U P A 2
H3BC H 0.423622 0.959080 0.506769 0.066 Uiso 0.471(15) 1 calc R U P A 2
C4B C 0.5220(5) 0.8211(10) 0.5640(7) 0.0443(8) Uani 0.471(15) 1 d D . P A 2
H4BA H 0.550719 0.758988 0.591184 0.066 Uiso 0.471(15) 1 calc R U P A 2
H4BB H 0.542240 0.905303 0.570813 0.066 Uiso 0.471(15) 1 calc R U P A 2
H4BC H 0.513955 0.795984 0.520706 0.066 Uiso 0.471(15) 1 calc R U P A 2
C5 C 0.41874(14) 0.6083(3) 0.55301(14) 0.0308(7) Uani 1 1 d . . . . .
C6 C 0.39710(13) 0.4905(3) 0.57990(12) 0.0230(6) Uani 1 1 d . . . . .
H6A H 0.384480 0.426226 0.545796 0.028 Uiso 1 1 calc R U . . .
C7 C 0.45355(14) 0.4319(3) 0.63166(13) 0.0275(6) Uani 1 1 d D . . . .
H7A H 0.436844 0.389173 0.662324 0.033 Uiso 0.530(3) 1 calc R U P B 1
H7B H 0.483477 0.499976 0.653190 0.033 Uiso 0.530(3) 1 calc R U P B 1
H7C H 0.470325 0.495875 0.664711 0.033 Uiso 0.470(3) 1 calc R U P B 2
H7D H 0.437428 0.358657 0.649915 0.033 Uiso 0.470(3) 1 calc R U P B 2
C8A C 0.4904(3) 0.3332(6) 0.6037(3) 0.0270(10) Uani 0.530(3) 1 d D . P A 1
H8AA H 0.502529 0.375080 0.569443 0.032 Uiso 0.530(3) 1 calc R U P B 1
O4A O 0.4528(2) 0.2220(4) 0.5797(2) 0.0391(8) Uani 0.530(3) 1 d D . P A 1
H4OA H 0.412(3) 0.198(8) 0.594(5) 0.17(5) Uiso 0.530(3) 1 d D . P B 1
C8B C 0.5087(3) 0.3870(7) 0.6084(3) 0.0270(10) Uani 0.470(3) 1 d D . P A 2
H8BA H 0.489145 0.329326 0.572500 0.032 Uiso 0.470(3) 1 calc R U P B 2
O4B O 0.5359(2) 0.4921(4) 0.5852(2) 0.0391(8) Uani 0.470(3) 1 d D . P A 2
H4OB H 0.527(5) 0.436(8) 0.544(3) 0.09(3) Uiso 0.470(3) 1 d D . P B 2
C11 C 0.29993(13) 0.3867(3) 0.59964(12) 0.0237(6) Uani 1 1 d . . . . .
C12 C 0.24151(14) 0.3768(3) 0.61212(14) 0.0285(6) Uani 1 1 d . . . . .
C13 C 0.20920(16) 0.2616(3) 0.60473(16) 0.0368(7) Uani 1 1 d . . . . .
H13A H 0.169314 0.255090 0.613023 0.044 Uiso 1 1 calc R U . . .
C14 C 0.23522(16) 0.1570(3) 0.58535(15) 0.0373(8) Uani 1 1 d . . . . .
H14A H 0.213685 0.077212 0.579158 0.045 Uiso 1 1 calc R U . . .
C15 C 0.29376(17) 0.1720(3) 0.57522(15) 0.0372(8) Uani 1 1 d . . . . .
H15A H 0.312812 0.099706 0.562888 0.045 Uiso 1 1 calc R U . . .
C21 C 0.29238(13) 0.6055(3) 0.55300(13) 0.0226(6) Uani 1 1 d . . . . .
C22 C 0.33604(13) 0.5130(2) 0.60086(12) 0.0211(5) Uani 1 1 d . . . . .
C23 C 0.34963(13) 0.5906(3) 0.65971(12) 0.0214(5) Uani 1 1 d . . . . .
C24 C 0.38083(14) 0.5610(3) 0.72097(13) 0.0267(6) Uani 1 1 d . . . . .
H24A H 0.397638 0.478126 0.732437 0.032 Uiso 1 1 calc R U . . .
C25 C 0.38713(16) 0.6550(3) 0.76554(14) 0.0349(7) Uani 1 1 d . . . . .
H25A H 0.408758 0.635933 0.807770 0.042 Uiso 1 1 calc R U . . .
C26 C 0.36262(16) 0.7751(3) 0.74953(15) 0.0356(7) Uani 1 1 d . . . . .
H26A H 0.367990 0.837868 0.780806 0.043 Uiso 1 1 calc R U . . .
C27 C 0.32999(14) 0.8062(3) 0.68808(14) 0.0296(6) Uani 1 1 d . . . . .
H27A H 0.312669 0.888788 0.676732 0.036 Uiso 1 1 calc R U . . .
C28 C 0.32397(13) 0.7119(3) 0.64454(13) 0.0223(6) Uani 1 1 d . . . . .
C31A C 0.5515(3) 0.2972(14) 0.6546(5) 0.031(3) Uani 0.529(15) 1 d DG . P A 1
C32A C 0.5506(4) 0.2133(13) 0.7016(5) 0.035(2) Uani 0.529(15) 1 d G . P A 1
H32A H 0.510767 0.180995 0.703756 0.042 Uiso 0.529(15) 1 calc R U P A 1
C33A C 0.6080(6) 0.1765(10) 0.7453(4) 0.053(3) Uani 0.529(15) 1 d G . P A 1
H33A H 0.607386 0.119181 0.777409 0.064 Uiso 0.529(15) 1 calc R U P A 1
C34A C 0.6663(4) 0.2238(12) 0.7421(4) 0.056(3) Uani 0.529(15) 1 d G . P A 1
H34A H 0.705519 0.198656 0.772023 0.067 Uiso 0.529(15) 1 calc R U P A 1
C35A C 0.6672(3) 0.3077(12) 0.6952(5) 0.059(3) Uani 0.529(15) 1 d G . P A 1
H35A H 0.707034 0.339946 0.692983 0.071 Uiso 0.529(15) 1 calc R U P A 1
C36A C 0.6098(5) 0.3444(11) 0.6514(5) 0.043(2) Uani 0.529(15) 1 d G . P A 1
H36A H 0.610416 0.401761 0.619328 0.052 Uiso 0.529(15) 1 calc R U P A 1
C31B C 0.5615(5) 0.3107(15) 0.6551(6) 0.030(3) Uani 0.471(15) 1 d DG . P A 2
C32B C 0.5413(3) 0.2157(14) 0.6873(7) 0.040(3) Uani 0.471(15) 1 d G . P A 2
H32B H 0.496846 0.195309 0.676985 0.049 Uiso 0.471(15) 1 calc R U P A 2
C33B C 0.5862(5) 0.1504(10) 0.7347(5) 0.042(3) Uani 0.471(15) 1 d G . P A 2
H33B H 0.572376 0.085450 0.756718 0.051 Uiso 0.471(15) 1 calc R U P A 2
C34B C 0.6512(4) 0.1802(10) 0.7498(4) 0.042(3) Uani 0.471(15) 1 d G . P A 2
H34B H 0.681909 0.135594 0.782212 0.050 Uiso 0.471(15) 1 calc R U P A 2
C35B C 0.6714(3) 0.2752(9) 0.7176(5) 0.036(3) Uani 0.471(15) 1 d G . P A 2
H35B H 0.715913 0.295598 0.727973 0.043 Uiso 0.471(15) 1 calc R U P A 2
C36B C 0.6266(5) 0.3405(11) 0.6703(6) 0.039(3) Uani 0.471(15) 1 d G . P A 2
H36B H 0.640384 0.405458 0.648240 0.047 Uiso 0.471(15) 1 calc R U P A 2


_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
Br C12 1.894(3) . ?
O1 C5 1.327(4) . ?
O1 C1 1.486(4) . ?
O2 C5 1.205(4) . ?
O3 C21 1.230(3) . ?
N1 C15 1.340(4) . ?
N1 C11 1.341(4) . ?
N2 C21 1.346(3) . ?
N2 C28 1.406(4) . ?
C1 C4B 1.473(10) . ?
C1 C2B 1.484(9) . ?
C1 C3A 1.518(8) . ?
C1 C2A 1.553(9) . ?
C1 C4A 1.556(9) . ?
C1 C3B 1.560(9) . ?
C5 C6 1.520(4) . ?
C6 C7 1.542(4) . ?
C6 C22 1.569(4) . ?
C7 C8B 1.533(8) . ?
C7 C8A 1.564(7) . ?
C8A O4A 1.435(7) . ?
C8A C31A 1.517(7) . ?
C8B O4B 1.432(8) . ?
C8B C31B 1.528(9) . ?
C11 C12 1.396(4) . ?
C11 C22 1.540(4) . ?
C12 C13 1.385(4) . ?
C13 C14 1.373(5) . ?
C14 C15 1.378(5) . ?
C21 C22 1.546(4) . ?
C22 C23 1.515(4) . ?
C23 C24 1.382(4) . ?
C23 C28 1.392(4) . ?
C24 C25 1.391(4) . ?
C25 C26 1.375(5) . ?
C26 C27 1.395(4) . ?
C27 C28 1.378(4) . ?
C31A C32A 1.3900 . ?
C31A C36A 1.3900 . ?
C32A C33A 1.3900 . ?
C33A C34A 1.3900 . ?
C34A C35A 1.3900 . ?
C35A C36A 1.3900 . ?
C31B C32B 1.3900 . ?
C31B C36B 1.3900 . ?
C32B C33B 1.3900 . ?
C33B C34B 1.3900 . ?
C34B C35B 1.3900 . ?
C35B C36B 1.3900 . ?

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
C5 O1 C1 121.9(2) . . ?
C15 N1 C11 119.7(3) . . ?
C21 N2 C28 111.3(2) . . ?
C4B C1 C2B 114.6(7) . . ?
C4B C1 O1 115.6(5) . . ?
C2B C1 O1 103.7(5) . . ?
O1 C1 C3A 112.1(4) . . ?
O1 C1 C2A 100.2(4) . . ?
C3A C1 C2A 109.5(5) . . ?
O1 C1 C4A 104.1(4) . . ?
C3A C1 C4A 122.5(7) . . ?
C2A C1 C4A 106.0(6) . . ?
C4B C1 C3B 101.8(8) . . ?
C2B C1 C3B 112.9(5) . . ?
O1 C1 C3B 108.4(4) . . ?
O2 C5 O1 124.5(3) . . ?
O2 C5 C6 122.8(3) . . ?
O1 C5 C6 112.7(2) . . ?
C5 C6 C7 110.9(2) . . ?
C5 C6 C22 113.6(2) . . ?
C7 C6 C22 112.4(2) . . ?
C8B C7 C6 112.8(3) . . ?
C6 C7 C8A 110.2(3) . . ?
O4A C8A C31A 110.5(7) . . ?
O4A C8A C7 112.9(5) . . ?
C31A C8A C7 107.3(8) . . ?
O4B C8B C31B 110.5(7) . . ?
O4B C8B C7 110.6(5) . . ?
C31B C8B C7 115.3(8) . . ?
N1 C11 C12 119.4(3) . . ?
N1 C11 C22 116.6(2) . . ?
C12 C11 C22 123.9(2) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 Br 116.3(2) . . ?
C11 C12 Br 123.4(2) . . ?
C14 C13 C12 119.5(3) . . ?
C13 C14 C15 117.5(3) . . ?
N1 C15 C14 123.5(3) . . ?
O3 C21 N2 126.1(3) . . ?
O3 C21 C22 125.0(2) . . ?
N2 C21 C22 108.8(2) . . ?
C23 C22 C11 116.0(2) . . ?
C23 C22 C21 101.0(2) . . ?
C11 C22 C21 109.2(2) . . ?
C23 C22 C6 113.5(2) . . ?
C11 C22 C6 110.1(2) . . ?
C21 C22 C6 106.1(2) . . ?
C24 C23 C28 119.3(3) . . ?
C24 C23 C22 131.9(2) . . ?
C28 C23 C22 108.7(2) . . ?
C23 C24 C25 118.7(3) . . ?
C26 C25 C24 121.2(3) . . ?
C25 C26 C27 121.0(3) . . ?
C28 C27 C26 117.1(3) . . ?
C27 C28 C23 122.7(3) . . ?
C27 C28 N2 127.7(3) . . ?
C23 C28 N2 109.6(2) . . ?
C32A C31A C36A 120.0 . . ?
C32A C31A C8A 121.6(7) . . ?
C36A C31A C8A 118.2(7) . . ?
C33A C32A C31A 120.0 . . ?
C32A C33A C34A 120.0 . . ?
C35A C34A C33A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C35A C36A C31A 120.0 . . ?
C32B C31B C36B 120.0 . . ?
C32B C31B C8B 116.6(8) . . ?
C36B C31B C8B 123.1(8) . . ?
C31B C32B C33B 120.0 . . ?
C34B C33B C32B 120.0 . . ?
C33B C34B C35B 120.0 . . ?
C34B C35B C36B 120.0 . . ?
C35B C36B C31B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C4B -66.4(8) . . . . ?
C5 O1 C1 C2B 167.2(5) . . . . ?
C5 O1 C1 C3A 68.0(6) . . . . ?
C5 O1 C1 C2A -175.8(4) . . . . ?
C5 O1 C1 C4A -66.3(6) . . . . ?
C5 O1 C1 C3B 47.1(6) . . . . ?
C1 O1 C5 O2 -0.8(5) . . . . ?
C1 O1 C5 C6 179.6(2) . . . . ?
O2 C5 C6 C7 115.9(3) . . . . ?
O1 C5 C6 C7 -64.5(3) . . . . ?
O2 C5 C6 C22 -116.3(3) . . . . ?
O1 C5 C6 C22 63.3(3) . . . . ?
C5 C6 C7 C8B -62.1(4) . . . . ?
C22 C6 C7 C8B 169.5(4) . . . . ?
C5 C6 C7 C8A -89.3(4) . . . . ?
C22 C6 C7 C8A 142.3(3) . . . . ?
C6 C7 C8A O4A -67.9(5) . . . . ?
C6 C7 C8A C31A 170.2(5) . . . . ?
C6 C7 C8B O4B 62.4(6) . . . . ?
C6 C7 C8B C31B -171.4(7) . . . . ?
C15 N1 C11 C12 1.1(4) . . . . ?
C15 N1 C11 C22 -175.0(3) . . . . ?
N1 C11 C12 C13 -1.6(4) . . . . ?
C22 C11 C12 C13 174.3(3) . . . . ?
N1 C11 C12 Br 179.1(2) . . . . ?
C22 C11 C12 Br -5.1(4) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
Br C12 C13 C14 179.7(2) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C11 N1 C15 C14 0.5(5) . . . . ?
C13 C14 C15 N1 -1.7(5) . . . . ?
C28 N2 C21 O3 177.6(3) . . . . ?
C28 N2 C21 C22 -5.7(3) . . . . ?
N1 C11 C22 C23 -130.5(3) . . . . ?
C12 C11 C22 C23 53.5(4) . . . . ?
N1 C11 C22 C21 116.2(3) . . . . ?
C12 C11 C22 C21 -59.7(3) . . . . ?
N1 C11 C22 C6 0.1(3) . . . . ?
C12 C11 C22 C6 -175.8(3) . . . . ?
O3 C21 C22 C23 -175.9(3) . . . . ?
N2 C21 C22 C23 7.3(3) . . . . ?
O3 C21 C22 C11 -53.2(4) . . . . ?
N2 C21 C22 C11 130.0(2) . . . . ?
O3 C21 C22 C6 65.4(3) . . . . ?
N2 C21 C22 C6 -111.4(2) . . . . ?
C5 C6 C22 C23 -73.2(3) . . . . ?
C7 C6 C22 C23 53.8(3) . . . . ?
C5 C6 C22 C11 154.9(2) . . . . ?
C7 C6 C22 C11 -78.1(3) . . . . ?
C5 C6 C22 C21 36.8(3) . . . . ?
C7 C6 C22 C21 163.8(2) . . . . ?
C11 C22 C23 C24 55.4(4) . . . . ?
C21 C22 C23 C24 173.3(3) . . . . ?
C6 C22 C23 C24 -73.6(4) . . . . ?
C11 C22 C23 C28 -124.3(3) . . . . ?
C21 C22 C23 C28 -6.4(3) . . . . ?
C6 C22 C23 C28 106.7(3) . . . . ?
C28 C23 C24 C25 -1.7(4) . . . . ?
C22 C23 C24 C25 178.6(3) . . . . ?
C23 C24 C25 C26 0.4(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C28 -0.4(5) . . . . ?
C26 C27 C28 C23 -0.9(4) . . . . ?
C26 C27 C28 N2 176.9(3) . . . . ?
C24 C23 C28 C27 2.0(4) . . . . ?
C22 C23 C28 C27 -178.2(3) . . . . ?
C24 C23 C28 N2 -176.1(2) . . . . ?
C22 C23 C28 N2 3.6(3) . . . . ?
C21 N2 C28 C27 -176.7(3) . . . . ?
C21 N2 C28 C23 1.4(3) . . . . ?
O4A C8A C31A C32A -46.3(10) . . . . ?
C7 C8A C31A C32A 77.2(9) . . . . ?
O4A C8A C31A C36A 129.9(7) . . . . ?
C7 C8A C31A C36A -106.6(8) . . . . ?
C36A C31A C32A C33A 0.0 . . . . ?
C8A C31A C32A C33A 176.1(13) . . . . ?
C31A C32A C33A C34A 0.0 . . . . ?
C32A C33A C34A C35A 0.0 . . . . ?
C33A C34A C35A C36A 0.0 . . . . ?
C34A C35A C36A C31A 0.0 . . . . ?
C32A C31A C36A C35A 0.0 . . . . ?
C8A C31A C36A C35A -176.3(13) . . . . ?
O4B C8B C31B C32B 172.0(7) . . . . ?
C7 C8B C31B C32B 45.7(11) . . . . ?
O4B C8B C31B C36B -1.7(14) . . . . ?
C7 C8B C31B C36B -127.9(9) . . . . ?
C36B C31B C32B C33B 0.0 . . . . ?
C8B C31B C32B C33B -173.8(14) . . . . ?
C31B C32B C33B C34B 0.0 . . . . ?
C32B C33B C34B C35B 0.0 . . . . ?
C33B C34B C35B C36B 0.0 . . . . ?
C34B C35B C36B C31B 0.0 . . . . ?
C32B C31B C36B C35B 0.0 . . . . ?
C8B C31B C36B C35B 173.4(15) . . . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA, Hexane'
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1984207'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H27 Br N2 O4'
_chemical_formula_sum            'C28 H27 Br N2 O4'
_chemical_formula_weight         535.42

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

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

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

_cell_length_a                   10.9570(13)
_cell_length_b                   22.742(2)
_cell_length_c                   11.1670(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.062(4)
_cell_angle_gamma                90
_cell_volume                     2613.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4019
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.92

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.608
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5994
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48394
_diffrn_reflns_av_unetI/netI     0.1143
_diffrn_reflns_av_R_equivalents  0.1800
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.642
_diffrn_reflns_theta_max         28.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6514
_reflns_number_gt                3349
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0445P)²+1.7411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6514
_refine_ls_number_parameters     324
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
Br Br 0.97908(5) 0.39264(2) 0.83535(4) 0.04444(16) Uani 1 1 d . . . . .
O1 O 1.0184(3) 0.41484(11) 0.4947(2) 0.0302(6) Uani 1 1 d . . . . .
O2 O 0.5961(3) 0.41470(13) 0.2668(3) 0.0466(8) Uani 1 1 d . . . . .
O3 O 0.7908(3) 0.40982(11) 0.2400(2) 0.0328(7) Uani 1 1 d . . . . .
O4 O 0.6249(3) 0.28148(13) 0.1691(3) 0.0440(8) Uani 1 1 d . . . . .
N1 N 0.8638(3) 0.47075(14) 0.5387(3) 0.0269(7) Uani 1 1 d D . . . .
H1N H 0.892(4) 0.5022(14) 0.532(4) 0.027(11) Uiso 1 1 d D . . . .
N2 N 0.9069(4) 0.26689(14) 0.5541(3) 0.0446(10) Uani 1 1 d . . . . .
C1 C 0.9182(4) 0.41977(16) 0.5188(3) 0.0265(8) Uani 1 1 d . . . . .
C2 C 0.8270(4) 0.36873(16) 0.5290(3) 0.0276(9) Uani 1 1 d . . . . .
C3 C 0.7562(4) 0.34502(16) 0.3892(4) 0.0305(9) Uani 1 1 d . . . . .
H3 H 0.820431 0.321857 0.362931 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6427(4) 0.30426(17) 0.3840(4) 0.0369(10) Uani 1 1 d . . . . .
H4A H 0.673779 0.274375 0.452238 0.044 Uiso 1 1 calc R U . . .
H4B H 0.574196 0.327665 0.400882 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5850(4) 0.27355(17) 0.2578(4) 0.0336(10) Uani 1 1 d . . . . .
C6 C 0.7036(4) 0.39366(18) 0.2931(4) 0.0332(9) Uani 1 1 d . . . . .
C7 C 0.7606(5) 0.45372(18) 0.1358(4) 0.0413(11) Uani 1 1 d . . . . .
C8 C 0.8867(6) 0.4576(2) 0.1104(5) 0.0591(15) Uani 1 1 d . . . . .
H8A H 0.910666 0.418453 0.088989 0.089 Uiso 1 1 calc R U . . .
H8B H 0.955055 0.472305 0.186613 0.089 Uiso 1 1 calc R U . . .
H8C H 0.876459 0.484449 0.039003 0.089 Uiso 1 1 calc R U . . .
C9 C 0.7293(5) 0.51248(19) 0.1839(5) 0.0543(13) Uani 1 1 d . . . . .
H9A H 0.798822 0.522927 0.263390 0.081 Uiso 1 1 calc R U . . .
H9B H 0.646839 0.509437 0.199530 0.081 Uiso 1 1 calc R U . . .
H9C H 0.722219 0.542919 0.119728 0.081 Uiso 1 1 calc R U . . .
C10 C 0.6517(7) 0.4304(2) 0.0220(5) 0.083(2) Uani 1 1 d . . . . .
H10A H 0.673803 0.390808 0.001279 0.125 Uiso 1 1 calc R U . . .
H10B H 0.639144 0.456420 -0.051168 0.125 Uiso 1 1 calc R U . . .
H10C H 0.571345 0.428730 0.041999 0.125 Uiso 1 1 calc R U . . .
C11 C 0.7569(4) 0.46088(16) 0.5794(3) 0.0263(8) Uani 1 1 d . . . . .
C12 C 0.7341(4) 0.40075(16) 0.5799(3) 0.0268(8) Uani 1 1 d . . . . .
C13 C 0.6404(4) 0.38026(18) 0.6266(4) 0.0319(9) Uani 1 1 d . . . . .
H13 H 0.625178 0.339284 0.630075 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5691(4) 0.42080(19) 0.6683(4) 0.0378(10) Uani 1 1 d . . . . .
H14 H 0.503244 0.407399 0.699206 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5926(4) 0.48048(19) 0.6655(4) 0.0384(10) Uani 1 1 d . . . . .
H15 H 0.542021 0.507234 0.694164 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6888(4) 0.50261(17) 0.6215(4) 0.0318(9) Uani 1 1 d . . . . .
C17 C 0.7175(4) 0.56778(17) 0.6217(4) 0.0438(11) Uani 1 1 d . . . . .
H17A H 0.707247 0.580478 0.534947 0.066 Uiso 1 1 calc R U . . .
H17B H 0.806797 0.575336 0.678043 0.066 Uiso 1 1 calc R U . . .
H17C H 0.656957 0.589695 0.652321 0.066 Uiso 1 1 calc R U . . .
C21 C 0.9022(4) 0.31782(16) 0.6136(4) 0.0294(9) Uani 1 1 d . . . . .
C22 C 0.9621(4) 0.32099(17) 0.7444(4) 0.0343(10) Uani 1 1 d . . . . .
C23 C 1.0181(5) 0.27170(19) 0.8150(4) 0.0453(12) Uani 1 1 d . . . . .
H23 H 1.056875 0.274008 0.905110 0.054 Uiso 1 1 calc R U . . .
C24 C 1.0168(5) 0.2197(2) 0.7529(5) 0.0551(14) Uani 1 1 d . . . . .
H24 H 1.052054 0.184855 0.798669 0.066 Uiso 1 1 calc R U . . .
C25 C 0.9632(6) 0.2196(2) 0.6237(5) 0.0558(14) Uani 1 1 d . . . . .
H25 H 0.965627 0.184023 0.579842 0.067 Uiso 1 1 calc R U . . .
C31 C 0.4714(4) 0.23357(16) 0.2428(4) 0.0300(9) Uani 1 1 d . . . . .
C32 C 0.4552(4) 0.20598(17) 0.3460(4) 0.0354(10) Uani 1 1 d . . . . .
H32 H 0.515735 0.212796 0.429104 0.042 Uiso 1 1 calc R U . . .
C33 C 0.3517(4) 0.16851(18) 0.3300(4) 0.0417(11) Uani 1 1 d . . . . .
H33 H 0.342880 0.148680 0.401437 0.050 Uiso 1 1 calc R U . . .
C34 C 0.2612(4) 0.15985(17) 0.2106(4) 0.0395(11) Uani 1 1 d . . . . .
H34 H 0.189265 0.134548 0.200149 0.047 Uiso 1 1 calc R U . . .
C35 C 0.2743(4) 0.18763(18) 0.1063(4) 0.0427(11) Uani 1 1 d . . . . .
H35 H 0.211254 0.181985 0.024001 0.051 Uiso 1 1 calc R U . . .
C36 C 0.3800(4) 0.22382(18) 0.1223(4) 0.0390(11) Uani 1 1 d . . . . .
H36 H 0.390460 0.242295 0.050130 0.047 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
Br C22 1.895(4) . ?
O1 C1 1.221(5) . ?
O2 C6 1.210(5) . ?
O3 C6 1.337(5) . ?
O3 C7 1.482(5) . ?
O4 C5 1.225(5) . ?
N1 C1 1.357(5) . ?
N1 C11 1.412(5) . ?
N2 C21 1.345(5) . ?
N2 C25 1.347(6) . ?
C1 C2 1.561(5) . ?
C2 C12 1.513(5) . ?
C2 C21 1.542(5) . ?
C2 C3 1.580(5) . ?
C3 C6 1.511(5) . ?
C3 C4 1.536(5) . ?
C4 C5 1.504(5) . ?
C5 C31 1.504(6) . ?
C7 C8 1.506(7) . ?
C7 C10 1.510(6) . ?
C7 C9 1.522(6) . ?
C11 C16 1.385(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.389(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.400(6) . ?
C16 C17 1.515(5) . ?
C21 C22 1.382(5) . ?
C22 C23 1.387(6) . ?
C23 C24 1.368(6) . ?
C24 C25 1.359(7) . ?
C31 C32 1.377(5) . ?
C31 C36 1.392(5) . ?
C32 C33 1.380(6) . ?
C33 C34 1.375(6) . ?
C34 C35 1.375(6) . ?
C35 C36 1.382(6) . ?

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 O3 C7 122.1(3) . . ?
C1 N1 C11 112.1(3) . . ?
C21 N2 C25 119.4(4) . . ?
O1 C1 N1 126.4(3) . . ?
O1 C1 C2 126.4(3) . . ?
N1 C1 C2 107.2(3) . . ?
C12 C2 C21 114.7(3) . . ?
C12 C2 C1 101.5(3) . . ?
C21 C2 C1 112.5(3) . . ?
C12 C2 C3 111.7(3) . . ?
C21 C2 C3 109.1(3) . . ?
C1 C2 C3 106.9(3) . . ?
C6 C3 C4 108.0(3) . . ?
C6 C3 C2 113.0(3) . . ?
C4 C3 C2 111.1(3) . . ?
C5 C4 C3 112.9(3) . . ?
O4 C5 C31 120.7(4) . . ?
O4 C5 C4 122.5(4) . . ?
C31 C5 C4 116.8(3) . . ?
O2 C6 O3 124.6(4) . . ?
O2 C6 C3 124.3(4) . . ?
O3 C6 C3 111.1(4) . . ?
O3 C7 C8 102.4(4) . . ?
O3 C7 C10 108.9(3) . . ?
C8 C7 C10 111.9(4) . . ?
O3 C7 C9 109.4(3) . . ?
C8 C7 C9 110.3(4) . . ?
C10 C7 C9 113.4(4) . . ?
C16 C11 C12 123.6(4) . . ?
C16 C11 N1 127.1(3) . . ?
C12 C11 N1 109.1(3) . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 C2 131.5(3) . . ?
C11 C12 C2 109.1(3) . . ?
C12 C13 C14 118.6(4) . . ?
C15 C14 C13 120.8(4) . . ?
C14 C15 C16 122.0(4) . . ?
C11 C16 C15 115.5(4) . . ?
C11 C16 C17 122.4(4) . . ?
C15 C16 C17 122.1(4) . . ?
N2 C21 C22 118.8(4) . . ?
N2 C21 C2 116.5(3) . . ?
C22 C21 C2 124.7(3) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 Br 122.3(3) . . ?
C23 C22 Br 116.6(3) . . ?
C24 C23 C22 119.0(4) . . ?
C25 C24 C23 117.7(4) . . ?
N2 C25 C24 123.8(4) . . ?
C32 C31 C36 118.7(4) . . ?
C32 C31 C5 121.5(3) . . ?
C36 C31 C5 119.8(4) . . ?
C31 C32 C33 120.6(4) . . ?
C34 C33 C32 120.1(4) . . ?
C35 C34 C33 120.3(4) . . ?
C34 C35 C36 119.4(4) . . ?
C35 C36 C31 120.9(4) . . ?

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
C11 N1 C1 O1 -172.8(4) . . . . ?
C11 N1 C1 C2 8.6(4) . . . . ?
O1 C1 C2 C12 171.6(4) . . . . ?
N1 C1 C2 C12 -9.8(4) . . . . ?
O1 C1 C2 C21 48.5(5) . . . . ?
N1 C1 C2 C21 -132.9(3) . . . . ?
O1 C1 C2 C3 -71.2(5) . . . . ?
N1 C1 C2 C3 107.4(3) . . . . ?
C12 C2 C3 C6 64.2(4) . . . . ?
C21 C2 C3 C6 -167.9(3) . . . . ?
C1 C2 C3 C6 -46.0(4) . . . . ?
C12 C2 C3 C4 -57.2(4) . . . . ?
C21 C2 C3 C4 70.6(4) . . . . ?
C1 C2 C3 C4 -167.5(3) . . . . ?
C6 C3 C4 C5 64.2(4) . . . . ?
C2 C3 C4 C5 -171.4(3) . . . . ?
C3 C4 C5 O4 -0.9(6) . . . . ?
C3 C4 C5 C31 -178.8(3) . . . . ?
C7 O3 C6 O2 -3.8(6) . . . . ?
C7 O3 C6 C3 175.5(3) . . . . ?
C4 C3 C6 O2 33.9(5) . . . . ?
C2 C3 C6 O2 -89.4(5) . . . . ?
C4 C3 C6 O3 -145.4(3) . . . . ?
C2 C3 C6 O3 91.3(4) . . . . ?
C6 O3 C7 C8 179.2(3) . . . . ?
C6 O3 C7 C10 -62.2(5) . . . . ?
C6 O3 C7 C9 62.2(5) . . . . ?
C1 N1 C11 C16 172.2(4) . . . . ?
C1 N1 C11 C12 -3.5(4) . . . . ?
C16 C11 C12 C13 -1.2(6) . . . . ?
N1 C11 C12 C13 174.7(3) . . . . ?
C16 C11 C12 C2 -179.4(3) . . . . ?
N1 C11 C12 C2 -3.5(4) . . . . ?
C21 C2 C12 C13 -48.5(5) . . . . ?
C1 C2 C12 C13 -170.0(4) . . . . ?
C3 C2 C12 C13 76.3(5) . . . . ?
C21 C2 C12 C11 129.4(3) . . . . ?
C1 C2 C12 C11 7.9(4) . . . . ?
C3 C2 C12 C11 -105.7(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C2 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C12 C11 C16 C15 -0.3(6) . . . . ?
N1 C11 C16 C15 -175.4(4) . . . . ?
C12 C11 C16 C17 179.0(4) . . . . ?
N1 C11 C16 C17 3.8(6) . . . . ?
C14 C15 C16 C11 1.0(6) . . . . ?
C14 C15 C16 C17 -178.2(4) . . . . ?
C25 N2 C21 C22 3.6(6) . . . . ?
C25 N2 C21 C2 -175.4(4) . . . . ?
C12 C2 C21 N2 133.4(4) . . . . ?
C1 C2 C21 N2 -111.3(4) . . . . ?
C3 C2 C21 N2 7.2(5) . . . . ?
C12 C2 C21 C22 -45.6(5) . . . . ?
C1 C2 C21 C22 69.8(5) . . . . ?
C3 C2 C21 C22 -171.7(4) . . . . ?
N2 C21 C22 C23 -4.6(6) . . . . ?
C2 C21 C22 C23 174.3(4) . . . . ?
N2 C21 C22 Br 172.5(3) . . . . ?
C2 C21 C22 Br -8.6(6) . . . . ?
C21 C22 C23 C24 1.8(7) . . . . ?
Br C22 C23 C24 -175.5(4) . . . . ?
C22 C23 C24 C25 1.8(8) . . . . ?
C21 N2 C25 C24 0.1(8) . . . . ?
C23 C24 C25 N2 -2.9(9) . . . . ?
O4 C5 C31 C32 154.5(4) . . . . ?
C4 C5 C31 C32 -27.5(6) . . . . ?
O4 C5 C31 C36 -25.4(6) . . . . ?
C4 C5 C31 C36 152.5(4) . . . . ?
C36 C31 C32 C33 1.3(6) . . . . ?
C5 C31 C32 C33 -178.7(4) . . . . ?
C31 C32 C33 C34 -2.1(7) . . . . ?
C32 C33 C34 C35 1.1(7) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 C35 C36 C31 -1.6(7) . . . . ?
C32 C31 C36 C35 0.6(6) . . . . ?
C5 C31 C36 C35 -179.5(4) . . . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.086



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
