# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_002
_database_code_depnum_ccdc_archive 'CCDC 1502141'
loop_
_audit_author_name
_audit_author_address
'Jiaming Liu' 'Yangzhou University'
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Br2 Cl N O3'
_chemical_formula_sum            'C22 H18 Br2 Cl N O3'
_chemical_formula_weight         539.62

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1923(11)
_cell_length_b                   10.0872(14)
_cell_length_c                   13.952(2)
_cell_angle_alpha                75.123(4)
_cell_angle_beta                 88.610(4)
_cell_angle_gamma                78.866(4)
_cell_volume                     1093.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    4693
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      24.12

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    3.853
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12899
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.53
_reflns_number_total             5034
_reflns_number_gt                2562
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0867P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4873
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1730
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.34052(8) -0.07460(6) 0.93664(5) 0.0667(3) Uani 1 1 d . . .
Br1 Br 0.61566(8) 0.59874(7) 0.89171(5) 0.0697(3) Uani 1 1 d . . .
Cl1 Cl -0.3090(2) 0.1280(2) 0.67515(16) 0.1023(7) Uani 1 1 d . . .
C3 C 0.0845(6) 0.1515(5) 0.7925(4) 0.0403(11) Uani 1 1 d . . .
H3 H 0.0848 0.0585 0.7894 0.048 Uiso 1 1 calc R . .
O1 O -0.0309(5) 0.4851(4) 0.6507(3) 0.0706(12) Uani 1 1 d . . .
C2 C 0.0793(6) 0.2454(5) 0.7059(4) 0.0389(11) Uani 1 1 d . . .
C1 C 0.0801(6) 0.3971(5) 0.6969(4) 0.0438(12) Uani 1 1 d . . .
C5 C 0.3611(6) 0.3509(5) 0.7832(4) 0.0460(13) Uani 1 1 d . . .
H5 H 0.3802 0.2572 0.7780 0.055 Uiso 1 1 calc R . .
C4 C 0.2137(6) 0.4396(5) 0.7461(3) 0.0422(12) Uani 1 1 d . . .
C22 C -0.0129(6) 0.2834(6) 0.9173(4) 0.0522(14) Uani 1 1 d . . .
H22 H -0.0849 0.3502 0.8681 0.063 Uiso 1 1 calc R . .
C6 C 0.4800(6) 0.3950(5) 0.8274(4) 0.0509(13) Uani 1 1 d . . .
H6 H 0.5796 0.3322 0.8545 0.061 Uiso 1 1 calc R . .
C17 C 0.0899(6) 0.1723(5) 0.8915(3) 0.0402(11) Uani 1 1 d . . .
C7 C 0.4531(6) 0.5317(5) 0.8319(4) 0.0470(12) Uani 1 1 d . . .
N1 N 0.0989(7) -0.0606(5) 0.6383(4) 0.0717(14) Uani 1 1 d . . .
C11 C 0.0810(7) 0.0560(6) 0.6245(4) 0.0509(13) Uani 1 1 d . . .
C18 C 0.1911(6) 0.0782(5) 0.9664(4) 0.0488(13) Uani 1 1 d . . .
C10 C 0.0606(7) 0.2079(5) 0.6077(4) 0.0466(13) Uani 1 1 d . . .
O2 O 0.2753(6) 0.3420(5) 0.5488(3) 0.0772(12) Uani 1 1 d . . .
C9 C 0.1918(6) 0.5785(5) 0.7504(4) 0.0467(13) Uani 1 1 d . . .
H9 H 0.0939 0.6422 0.7216 0.056 Uiso 1 1 calc R . .
C8 C 0.3077(7) 0.6246(5) 0.7949(4) 0.0533(14) Uani 1 1 d . . .
H8 H 0.2893 0.7182 0.8004 0.064 Uiso 1 1 calc R . .
C15 C -0.1087(7) 0.2802(6) 0.5492(4) 0.0588(15) Uani 1 1 d . . .
H15A H -0.0992 0.3757 0.5113 0.071 Uiso 1 1 calc R . .
H15B H -0.1260 0.2275 0.5007 0.071 Uiso 1 1 calc R . .
C20 C 0.0887(8) 0.2014(8) 1.0850(4) 0.0668(17) Uani 1 1 d . . .
H20 H 0.0874 0.2110 1.1510 0.080 Uiso 1 1 calc R . .
C12 C 0.1992(8) 0.2566(6) 0.5384(4) 0.0585(15) Uani 1 1 d . . .
C16 C -0.2645(8) 0.2903(7) 0.6147(6) 0.081(2) Uani 1 1 d . . .
H16A H -0.3618 0.3463 0.5725 0.097 Uiso 1 1 calc R . .
H16B H -0.2464 0.3402 0.6649 0.097 Uiso 1 1 calc R . .
C21 C -0.0134(8) 0.2995(7) 1.0124(5) 0.0671(17) Uani 1 1 d . . .
H21 H -0.0834 0.3774 1.0280 0.081 Uiso 1 1 calc R . .
C19 C 0.1910(7) 0.0911(6) 1.0621(4) 0.0567(15) Uani 1 1 d . . .
H19 H 0.2616 0.0237 1.1118 0.068 Uiso 1 1 calc R . .
O3 O 0.2120(6) 0.1985(5) 0.4640(3) 0.0877(14) Uani 1 1 d . . .
C13 C 0.3204(12) 0.2489(8) 0.3830(6) 0.120(3) Uani 1 1 d D . .
H13A H 0.2658 0.2591 0.3183 0.144 Uiso 1 1 calc R . .
H13B H 0.3411 0.3416 0.3854 0.144 Uiso 1 1 calc R . .
C14 C 0.4740(11) 0.1514(11) 0.3932(9) 0.190(6) Uani 1 1 d D . .
H14A H 0.5501 0.1729 0.4376 0.285 Uiso 1 1 calc R . .
H14B H 0.5238 0.1576 0.3280 0.285 Uiso 1 1 calc R . .
H14C H 0.4538 0.0565 0.4209 0.285 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
Br2 C18 1.903(5) . ?
Br1 C7 1.902(5) . ?
Cl1 C16 1.741(7) . ?
C3 C2 1.327(6) . ?
C3 C17 1.451(7) . ?
O1 C1 1.206(5) . ?
C2 C1 1.504(6) . ?
C2 C10 1.530(7) . ?
C1 C4 1.490(7) . ?
C5 C6 1.366(7) . ?
C5 C4 1.379(7) . ?
C4 C9 1.394(6) . ?
C22 C21 1.377(7) . ?
C22 C17 1.387(7) . ?
C6 C7 1.371(7) . ?
C17 C18 1.382(7) . ?
C7 C8 1.384(7) . ?
N1 C11 1.122(6) . ?
C11 C10 1.466(7) . ?
C18 C19 1.375(7) . ?
C10 C12 1.544(8) . ?
C10 C15 1.575(7) . ?
O2 C12 1.195(7) . ?
C9 C8 1.361(7) . ?
C15 C16 1.555(9) . ?
C20 C19 1.360(8) . ?
C20 C21 1.383(9) . ?
C12 O3 1.310(7) . ?
O3 C13 1.468(8) . ?
C13 C14 1.425(8) . ?

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
C2 C3 C17 128.5(4) . . ?
C3 C2 C1 122.9(4) . . ?
C3 C2 C10 121.8(4) . . ?
C1 C2 C10 115.2(4) . . ?
O1 C1 C4 119.7(4) . . ?
O1 C1 C2 119.2(4) . . ?
C4 C1 C2 121.0(4) . . ?
C6 C5 C4 121.4(5) . . ?
C5 C4 C9 118.2(5) . . ?
C5 C4 C1 123.6(4) . . ?
C9 C4 C1 118.1(4) . . ?
C21 C22 C17 121.8(5) . . ?
C5 C6 C7 118.8(5) . . ?
C18 C17 C22 116.4(5) . . ?
C18 C17 C3 121.7(5) . . ?
C22 C17 C3 121.8(4) . . ?
C8 C7 C6 121.7(5) . . ?
C8 C7 Br1 117.8(4) . . ?
C6 C7 Br1 120.4(4) . . ?
N1 C11 C10 178.9(6) . . ?
C19 C18 C17 122.8(5) . . ?
C19 C18 Br2 118.0(4) . . ?
C17 C18 Br2 119.2(4) . . ?
C11 C10 C2 110.2(4) . . ?
C11 C10 C12 108.0(4) . . ?
C2 C10 C12 108.6(4) . . ?
C11 C10 C15 109.0(4) . . ?
C2 C10 C15 114.7(4) . . ?
C12 C10 C15 106.1(4) . . ?
C8 C9 C4 121.4(5) . . ?
C9 C8 C7 118.3(5) . . ?
C16 C15 C10 115.0(5) . . ?
C19 C20 C21 120.1(5) . . ?
O2 C12 O3 125.5(6) . . ?
O2 C12 C10 124.0(5) . . ?
O3 C12 C10 110.3(5) . . ?
C15 C16 Cl1 113.2(4) . . ?
C22 C21 C20 119.6(6) . . ?
C20 C19 C18 119.3(5) . . ?
C12 O3 C13 117.5(6) . . ?
C14 C13 O3 109.1(7) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1520368'
loop_
_audit_author_name
_audit_author_address
'Jiaming Liu' 'Yangzhou University'
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 Br Cl N O3'
_chemical_formula_sum            'C22 H19 Br Cl N O3'
_chemical_formula_weight         460.73

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   15.6584(17)
_cell_length_b                   7.2134(7)
_cell_length_c                   19.131(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.956(3)
_cell_angle_gamma                90.00
_cell_volume                     2105.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6949
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      24.35

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22317
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4841
_reflns_number_gt                2970
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4822
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45943(2) 0.45343(5) 0.112137(19) 0.08741(18) Uani 1 1 d . . .
Cl1 Cl 0.82103(6) 0.52959(10) -0.09550(4) 0.0765(3) Uani 1 1 d . . .
C2 C 0.81978(14) 0.9537(3) 0.04991(12) 0.0390(5) Uani 1 1 d . . .
C1 C 0.83374(14) 0.8883(3) -0.01138(12) 0.0410(5) Uani 1 1 d . . .
H1 H 0.8895 0.8424 -0.0105 0.049 Uiso 1 1 calc R . .
C5 C 0.76033(15) 0.7271(3) -0.12458(12) 0.0454(6) Uani 1 1 d . . .
C4 C 0.76988(13) 0.8814(3) -0.08052(11) 0.0395(5) Uani 1 1 d . . .
O1 O 0.71293(12) 1.1797(2) 0.05540(12) 0.0705(5) Uani 1 1 d . . .
C9 C 0.72102(17) 1.0378(4) -0.10757(14) 0.0537(6) Uani 1 1 d . . .
H9 H 0.7265 1.1453 -0.0800 0.064 Uiso 1 1 calc R . .
O3 O 0.88948(16) 0.7231(3) 0.19369(11) 0.0828(6) Uani 1 1 d . . .
C17 C 0.66465(14) 0.8749(3) 0.06565(12) 0.0419(5) Uani 1 1 d . . .
C19 C 0.52149(17) 0.8086(4) 0.08548(15) 0.0622(7) Uani 1 1 d . . .
H19 H 0.4665 0.8490 0.0897 0.075 Uiso 1 1 calc R . .
C18 C 0.58240(16) 0.9325(4) 0.07293(14) 0.0532(6) Uani 1 1 d . . .
H18 H 0.5685 1.0579 0.0692 0.064 Uiso 1 1 calc R . .
C20 C 0.54259(17) 0.6243(4) 0.09168(14) 0.0571(6) Uani 1 1 d . . .
C10 C 0.89264(16) 0.9813(3) 0.11747(12) 0.0448(6) Uani 1 1 d . . .
C22 C 0.68312(16) 0.6860(3) 0.07041(14) 0.0536(6) Uani 1 1 d . . .
H22 H 0.7371 0.6435 0.0644 0.064 Uiso 1 1 calc R . .
O2 O 0.81463(18) 0.9686(4) 0.21114(13) 0.1002(8) Uani 1 1 d . . .
C8 C 0.6648(2) 1.0361(4) -0.17426(16) 0.0679(8) Uani 1 1 d . . .
H8 H 0.6327 1.1417 -0.1910 0.081 Uiso 1 1 calc R . .
C3 C 0.72951(16) 1.0160(3) 0.05638(13) 0.0443(5) Uani 1 1 d . . .
C7 C 0.65601(18) 0.8804(5) -0.21596(14) 0.0658(8) Uani 1 1 d . . .
H7 H 0.6177 0.8800 -0.2608 0.079 Uiso 1 1 calc R . .
C21 C 0.62212(18) 0.5615(4) 0.08396(16) 0.0613(7) Uani 1 1 d . . .
H21 H 0.6351 0.4356 0.0878 0.074 Uiso 1 1 calc R . .
C12 C 0.91230(18) 1.1902(4) 0.13396(14) 0.0602(7) Uani 1 1 d . . .
H12 H 0.8602 1.2455 0.1459 0.072 Uiso 1 1 calc R . .
N1 N 1.03833(16) 0.8263(4) 0.10222(13) 0.0762(7) Uani 1 1 d . . .
C11 C 0.97411(17) 0.8898(4) 0.10874(12) 0.0523(6) Uani 1 1 d . . .
C6 C 0.70389(17) 0.7244(4) -0.19153(13) 0.0585(7) Uani 1 1 d . . .
H6 H 0.6984 0.6181 -0.2197 0.070 Uiso 1 1 calc R . .
C15 C 0.86238(18) 0.8917(4) 0.18090(14) 0.0602(7) Uani 1 1 d . . .
C16 C 0.8559(4) 0.6285(6) 0.2498(2) 0.1285(17) Uani 1 1 d . . .
H16A H 0.8966 0.6434 0.2951 0.193 Uiso 1 1 calc R . .
H16B H 0.8486 0.4989 0.2385 0.193 Uiso 1 1 calc R . .
H16C H 0.8004 0.6810 0.2525 0.193 Uiso 1 1 calc R . .
C13 C 0.9304(2) 1.2935(4) 0.06984(17) 0.0784(9) Uani 1 1 d . . .
H13A H 0.9457 1.4196 0.0831 0.118 Uiso 1 1 calc R . .
H13B H 0.8789 1.2915 0.0315 0.118 Uiso 1 1 calc R . .
H13C H 0.9780 1.2349 0.0543 0.118 Uiso 1 1 calc R . .
C14 C 0.9887(2) 1.2153(5) 0.19875(19) 0.0997(12) Uani 1 1 d . . .
H14A H 1.0413 1.1673 0.1877 0.150 Uiso 1 1 calc R . .
H14B H 0.9765 1.1496 0.2391 0.150 Uiso 1 1 calc R . .
H14C H 0.9962 1.3447 0.2102 0.150 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C20 1.896(3) . ?
Cl1 C5 1.734(2) . ?
C2 C1 1.327(3) . ?
C2 C3 1.515(3) . ?
C2 C10 1.533(3) . ?
C1 C4 1.469(3) . ?
C5 C4 1.384(3) . ?
C5 C6 1.384(3) . ?
C4 C9 1.396(3) . ?
O1 C3 1.209(3) . ?
C9 C8 1.378(4) . ?
O3 C15 1.293(4) . ?
O3 C16 1.465(4) . ?
C17 C18 1.389(3) . ?
C17 C22 1.392(3) . ?
C17 C3 1.476(3) . ?
C19 C18 1.367(4) . ?
C19 C20 1.369(4) . ?
C20 C21 1.364(4) . ?
C10 C11 1.479(4) . ?
C10 C15 1.540(4) . ?
C10 C12 1.556(3) . ?
C22 C21 1.377(4) . ?
O2 C15 1.182(3) . ?
C8 C7 1.366(4) . ?
C7 C6 1.375(4) . ?
C12 C13 1.515(4) . ?
C12 C14 1.528(4) . ?
N1 C11 1.137(3) . ?

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 C2 C3 121.3(2) . . ?
C1 C2 C10 123.5(2) . . ?
C3 C2 C10 115.10(19) . . ?
C2 C1 C4 126.5(2) . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 Cl1 119.26(17) . . ?
C6 C5 Cl1 118.43(19) . . ?
C5 C4 C9 116.7(2) . . ?
C5 C4 C1 122.3(2) . . ?
C9 C4 C1 120.8(2) . . ?
C8 C9 C4 121.2(3) . . ?
C15 O3 C16 114.9(3) . . ?
C18 C17 C22 118.0(2) . . ?
C18 C17 C3 119.0(2) . . ?
C22 C17 C3 123.0(2) . . ?
C18 C19 C20 119.1(2) . . ?
C19 C18 C17 121.4(2) . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 Br1 119.5(2) . . ?
C19 C20 Br1 119.0(2) . . ?
C11 C10 C2 110.15(19) . . ?
C11 C10 C15 109.1(2) . . ?
C2 C10 C15 107.90(19) . . ?
C11 C10 C12 108.6(2) . . ?
C2 C10 C12 111.89(19) . . ?
C15 C10 C12 109.2(2) . . ?
C21 C22 C17 120.5(2) . . ?
C7 C8 C9 120.5(3) . . ?
O1 C3 C17 121.6(2) . . ?
O1 C3 C2 119.3(2) . . ?
C17 C3 C2 119.01(19) . . ?
C8 C7 C6 119.9(2) . . ?
C20 C21 C22 119.5(2) . . ?
C13 C12 C14 110.1(3) . . ?
C13 C12 C10 112.1(2) . . ?
C14 C12 C10 111.2(2) . . ?
N1 C11 C10 177.2(3) . . ?
C7 C6 C5 119.3(2) . . ?
O2 C15 O3 124.5(3) . . ?
O2 C15 C10 121.9(3) . . ?
O3 C15 C10 113.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_001_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1521488'
loop_
_audit_author_name
_audit_author_address
'Jiaming Liu' 'Yangzhou University'
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 N O4'
_chemical_formula_sum            'C25 H27 N O4'
_chemical_formula_weight         405.48

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   10.129(6)
_cell_length_b                   15.539(9)
_cell_length_c                   15.252(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.482(17)
_cell_angle_gamma                90.00
_cell_volume                     2313(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6227
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      23.55

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18808
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4069
_reflns_number_gt                2736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1162P)²+0.7050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     276
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.1954
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.158
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0611(2) 0.19761(12) 0.70302(14) 0.0581(6) Uani 1 1 d . . .
C2 C -0.0832(3) 0.05621(17) 0.75693(18) 0.0450(7) Uani 1 1 d . . .
C4 C 0.1323(3) 0.15142(16) 0.81895(18) 0.0445(7) Uani 1 1 d . . .
C1 C -0.0063(3) 0.14033(17) 0.75593(18) 0.0450(7) Uani 1 1 d . . .
O4 O 0.5109(2) 0.20661(16) 1.00083(17) 0.0779(7) Uani 1 1 d . . .
O3 O -0.1293(2) 0.16935(15) 0.90063(14) 0.0723(7) Uani 1 1 d . . .
C9 C 0.1911(3) 0.09289(18) 0.8878(2) 0.0522(7) Uani 1 1 d . . .
H9 H 0.1447 0.0421 0.8922 0.063 Uiso 1 1 calc R . .
C3 C -0.0420(3) -0.01746(18) 0.72736(19) 0.0494(7) Uani 1 1 d . . .
H3 H -0.0932 -0.0662 0.7319 0.059 Uiso 1 1 calc R . .
C7 C 0.3863(3) 0.1839(2) 0.9433(2) 0.0562(8) Uani 1 1 d . . .
C5 C 0.2061(3) 0.22693(18) 0.8133(2) 0.0529(7) Uani 1 1 d . . .
H5 H 0.1701 0.2668 0.7678 0.063 Uiso 1 1 calc R . .
C19 C 0.1058(3) 0.02796(19) 0.6266(2) 0.0543(8) Uani 1 1 d . . .
H19 H 0.0514 0.0767 0.6103 0.065 Uiso 1 1 calc R . .
C8 C 0.3170(3) 0.10831(19) 0.9500(2) 0.0572(8) Uani 1 1 d . . .
H8 H 0.3541 0.0685 0.9955 0.069 Uiso 1 1 calc R . .
C10 C -0.2150(3) 0.06199(18) 0.7896(2) 0.0513(7) Uani 1 1 d . . .
C18 C 0.0754(3) -0.03058(18) 0.68818(19) 0.0490(7) Uani 1 1 d . . .
C6 C 0.3305(3) 0.24266(19) 0.8740(2) 0.0584(8) Uani 1 1 d . . .
H6 H 0.3781 0.2928 0.8690 0.070 Uiso 1 1 calc R . .
C20 C 0.2161(3) 0.0149(2) 0.5891(2) 0.0588(8) Uani 1 1 d . . .
C17 C -0.2791(3) -0.0242(2) 0.7852(2) 0.0651(9) Uani 1 1 d . . .
N1 N -0.3324(3) -0.0896(2) 0.7793(3) 0.0917(11) Uani 1 1 d . . .
C23 C 0.1555(3) -0.1044(2) 0.7095(2) 0.0642(9) Uani 1 1 d . . .
H23 H 0.1349 -0.1453 0.7483 0.077 Uiso 1 1 calc R . .
O2 O -0.1993(4) 0.0479(2) 0.9498(2) 0.1222(12) Uani 1 1 d . . .
C14 C -0.3242(3) 0.1255(2) 0.7288(2) 0.0614(8) Uani 1 1 d . . .
H14 H -0.2825 0.1828 0.7339 0.074 Uiso 1 1 calc R . .
C21 C 0.2945(3) -0.0585(3) 0.6146(3) 0.0734(10) Uani 1 1 d . . .
H21 H 0.3690 -0.0681 0.5911 0.088 Uiso 1 1 calc R . .
C11 C -0.1800(3) 0.0906(2) 0.8898(2) 0.0641(9) Uani 1 1 d . . .
C22 C 0.2652(4) -0.1173(3) 0.6736(3) 0.0780(10) Uani 1 1 d . . .
H22 H 0.3195 -0.1660 0.6895 0.094 Uiso 1 1 calc R . .
C25 C 0.2449(4) 0.0793(3) 0.5225(3) 0.0845(11) Uani 1 1 d . . .
H25A H 0.3105 0.0557 0.4939 0.127 Uiso 1 1 calc R . .
H25B H 0.2810 0.1311 0.5542 0.127 Uiso 1 1 calc R . .
H25C H 0.1615 0.0921 0.4770 0.127 Uiso 1 1 calc R . .
C15 C -0.3605(4) 0.0996(3) 0.6278(2) 0.0770(10) Uani 1 1 d . . .
H15A H -0.3930 0.0413 0.6214 0.116 Uiso 1 1 calc R . .
H15B H -0.2806 0.1043 0.6057 0.116 Uiso 1 1 calc R . .
H15C H -0.4308 0.1371 0.5934 0.116 Uiso 1 1 calc R . .
C24 C 0.5700(4) 0.1524(3) 1.0770(3) 0.0923(13) Uani 1 1 d . . .
H24A H 0.5079 0.1473 1.1145 0.138 Uiso 1 1 calc R . .
H24B H 0.6547 0.1770 1.1118 0.138 Uiso 1 1 calc R . .
H24C H 0.5871 0.0964 1.0557 0.138 Uiso 1 1 calc R . .
C16 C -0.4520(4) 0.1321(3) 0.7635(3) 0.0908(12) Uani 1 1 d . . .
H16A H -0.5154 0.1719 0.7263 0.136 Uiso 1 1 calc R . .
H16B H -0.4268 0.1520 0.8253 0.136 Uiso 1 1 calc R . .
H16C H -0.4943 0.0765 0.7606 0.136 Uiso 1 1 calc R . .
C13 C 0.0434(7) 0.2057(6) 1.0358(5) 0.199(3) Uani 1 1 d DU . .
H13A H 0.0748 0.1471 1.0425 0.298 Uiso 1 1 calc R . .
H13B H 0.0591 0.2318 1.0947 0.298 Uiso 1 1 calc R . .
H13C H 0.0926 0.2369 1.0002 0.298 Uiso 1 1 calc R . .
C12 C -0.0965(5) 0.2073(3) 0.9919(3) 0.0991(14) Uani 1 1 d DU . .
H12A H -0.1281 0.2665 0.9872 0.119 Uiso 1 1 calc R . .
H12B H -0.1456 0.1763 1.0285 0.119 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
O1 C1 1.230(3) . ?
C2 C3 1.337(4) . ?
C2 C1 1.524(4) . ?
C2 C10 1.547(4) . ?
C4 C9 1.397(4) . ?
C4 C5 1.406(4) . ?
C4 C1 1.484(4) . ?
O4 C7 1.377(4) . ?
O4 C24 1.430(5) . ?
O3 C11 1.321(4) . ?
O3 C12 1.466(4) . ?
C9 C8 1.393(4) . ?
C3 C18 1.481(4) . ?
C7 C8 1.386(4) . ?
C7 C6 1.396(4) . ?
C5 C6 1.372(4) . ?
C19 C20 1.400(4) . ?
C19 C18 1.399(4) . ?
C10 C17 1.483(4) . ?
C10 C11 1.539(5) . ?
C10 C14 1.585(4) . ?
C18 C23 1.393(4) . ?
C20 C21 1.385(5) . ?
C20 C25 1.508(5) . ?
C17 N1 1.142(4) . ?
C23 C22 1.378(5) . ?
O2 C11 1.188(4) . ?
C14 C16 1.527(5) . ?
C14 C15 1.539(5) . ?
C21 C22 1.369(5) . ?
C13 C12 1.397(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
C3 C2 C1 121.6(2) . . ?
C3 C2 C10 122.1(2) . . ?
C1 C2 C10 116.2(2) . . ?
C9 C4 C5 117.5(3) . . ?
C9 C4 C1 123.4(2) . . ?
C5 C4 C1 118.9(2) . . ?
O1 C1 C4 121.6(2) . . ?
O1 C1 C2 119.0(2) . . ?
C4 C1 C2 119.4(2) . . ?
C7 O4 C24 118.7(3) . . ?
C11 O3 C12 118.3(3) . . ?
C8 C9 C4 122.0(3) . . ?
C2 C3 C18 127.6(2) . . ?
O4 C7 C8 124.4(3) . . ?
O4 C7 C6 115.6(3) . . ?
C8 C7 C6 120.0(3) . . ?
C6 C5 C4 121.0(3) . . ?
C20 C19 C18 121.5(3) . . ?
C7 C8 C9 119.0(3) . . ?
C17 C10 C11 106.7(3) . . ?
C17 C10 C2 109.8(2) . . ?
C11 C10 C2 110.3(2) . . ?
C17 C10 C14 107.9(3) . . ?
C11 C10 C14 109.9(2) . . ?
C2 C10 C14 112.1(2) . . ?
C23 C18 C19 118.2(3) . . ?
C23 C18 C3 120.0(3) . . ?
C19 C18 C3 121.7(3) . . ?
C5 C6 C7 120.5(3) . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 C25 122.4(3) . . ?
C19 C20 C25 119.9(3) . . ?
N1 C17 C10 177.5(4) . . ?
C22 C23 C18 120.5(3) . . ?
C16 C14 C15 111.4(3) . . ?
C16 C14 C10 111.3(3) . . ?
C15 C14 C10 111.4(3) . . ?
C22 C21 C20 121.7(3) . . ?
O2 C11 O3 124.0(3) . . ?
O2 C11 C10 124.2(3) . . ?
O3 C11 C10 111.7(3) . . ?
C21 C22 C23 120.2(3) . . ?
C13 C12 O3 113.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_001_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1517890'
loop_
_audit_author_name
_audit_author_address
'Jiaming Liu' 'Yangzhou University'
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Br Cl N O3'
_chemical_formula_sum            'C23 H21 Br Cl N O3'
_chemical_formula_weight         474.76

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

loop_
_symmetry_equiv_pos_as_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                   24.318(3)
_cell_length_b                   9.2383(11)
_cell_length_c                   20.240(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.433(4)
_cell_angle_gamma                90.00
_cell_volume                     4518.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296
_cell_measurement_reflns_used    5345
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      21.49

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32898
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.57
_reflns_number_total             5163
_reflns_number_gt                2104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0588P)²+4.5437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.08905(2) 0.28366(7) -0.00055(3) 0.1199(3) Uani 1 1 d . . .
Cl1 Cl 0.94444(8) 0.6625(2) 0.30364(9) 0.1511(7) Uani 1 1 d . . .
O3 O 0.71194(13) 0.2673(3) 0.12501(14) 0.0846(9) Uani 1 1 d . . .
C18 C 0.88905(15) 0.2462(5) 0.20281(18) 0.0630(11) Uani 1 1 d . . .
O1 O 0.88000(12) -0.0066(4) 0.20341(14) 0.0852(9) Uani 1 1 d . . .
C3 C 0.86851(14) 0.1055(5) 0.17430(19) 0.0633(11) Uani 1 1 d . . .
C15 C 0.74742(16) 0.1791(5) 0.1562(2) 0.0665(11) Uani 1 1 d . . .
O2 O 0.76216(12) 0.1833(4) 0.21460(15) 0.0962(10) Uani 1 1 d . . .
C11 C 0.74013(15) 0.0672(4) 0.0442(2) 0.0569(10) Uani 1 1 d . . .
C1 C 0.85250(14) 0.1360(4) 0.05242(18) 0.0582(10) Uani 1 1 d . . .
H1 H 0.8269 0.1355 0.0134 0.070 Uiso 1 1 calc R . .
C4 C 0.90997(15) 0.1708(4) 0.04299(18) 0.0592(10) Uani 1 1 d . . .
C2 C 0.83191(14) 0.1050(4) 0.10881(17) 0.0559(10) Uani 1 1 d . . .
C19 C 0.87351(17) 0.3778(6) 0.1743(2) 0.0786(12) Uani 1 1 d . . .
H19 H 0.8504 0.3803 0.1332 0.094 Uiso 1 1 calc R . .
C10 C 0.77084(14) 0.0659(4) 0.11152(16) 0.0545(9) Uani 1 1 d . . .
C9 C 0.95491(16) 0.0964(5) 0.07508(19) 0.0706(11) Uani 1 1 d . . .
H9 H 0.9491 0.0220 0.1059 0.085 Uiso 1 1 calc R . .
C7 C 1.01597(17) 0.2388(5) 0.0181(2) 0.0747(12) Uani 1 1 d . . .
C12 C 0.76224(15) -0.0859(5) 0.14230(19) 0.0707(12) Uani 1 1 d . . .
H12 H 0.7825 -0.0860 0.1881 0.085 Uiso 1 1 calc R . .
C6 C 0.97245(19) 0.3130(5) -0.0143(2) 0.0818(13) Uani 1 1 d . . .
H6 H 0.9785 0.3879 -0.0448 0.098 Uiso 1 1 calc R . .
C21 C 0.9245(2) 0.5010(6) 0.2637(2) 0.0900(14) Uani 1 1 d . . .
N1 N 0.71686(14) 0.0592(4) -0.00728(17) 0.0731(10) Uani 1 1 d . . .
C8 C 1.00818(17) 0.1301(6) 0.0623(2) 0.0785(13) Uani 1 1 d . . .
H8 H 1.0389 0.0786 0.0838 0.094 Uiso 1 1 calc R . .
C5 C 0.91997(17) 0.2773(5) -0.0019(2) 0.0736(12) Uani 1 1 d . . .
H5 H 0.8895 0.3274 -0.0249 0.088 Uiso 1 1 calc R . .
C23 C 0.92403(16) 0.2461(6) 0.2616(2) 0.0731(12) Uani 1 1 d . . .
H23 H 0.9361 0.1566 0.2814 0.088 Uiso 1 1 calc R . .
C22 C 0.94146(18) 0.3731(7) 0.2916(2) 0.0883(14) Uani 1 1 d . . .
H22 H 0.9654 0.3716 0.3321 0.106 Uiso 1 1 calc R . .
C14 C 0.70113(17) -0.1133(6) 0.1492(2) 0.0945(15) Uani 1 1 d . . .
H14A H 0.6801 -0.1153 0.1050 0.142 Uiso 1 1 calc R . .
H14B H 0.6870 -0.0358 0.1757 0.142 Uiso 1 1 calc R . .
H14C H 0.6972 -0.2065 0.1713 0.142 Uiso 1 1 calc R . .
C20 C 0.8912(2) 0.5068(6) 0.2049(2) 0.0900(14) Uani 1 1 d . . .
H20 H 0.8804 0.5972 0.1853 0.108 Uiso 1 1 calc R . .
C16 C 0.6917(2) 0.3844(7) 0.1670(3) 0.125(2) Uani 1 1 d . . .
H16A H 0.6710 0.3415 0.2015 0.151 Uiso 1 1 calc R . .
H16B H 0.7236 0.4386 0.1895 0.151 Uiso 1 1 calc R . .
C13 C 0.7869(2) -0.2049(5) 0.1037(3) 0.0997(15) Uani 1 1 d . . .
H13A H 0.7813 -0.2984 0.1248 0.150 Uiso 1 1 calc R . .
H13B H 0.8266 -0.1874 0.1032 0.150 Uiso 1 1 calc R . .
H13C H 0.7687 -0.2059 0.0579 0.150 Uiso 1 1 calc R . .
C17 C 0.6584(3) 0.4756(7) 0.1283(3) 0.150(3) Uani 1 1 d . . .
H17A H 0.6788 0.5158 0.0934 0.224 Uiso 1 1 calc R . .
H17B H 0.6464 0.5546 0.1557 0.224 Uiso 1 1 calc R . .
H17C H 0.6260 0.4226 0.1079 0.224 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.903(4) . ?
Cl1 C21 1.741(5) . ?
O3 C15 1.298(5) . ?
O3 C16 1.493(5) . ?
C18 C19 1.381(6) . ?
C18 C23 1.383(5) . ?
C18 C3 1.485(6) . ?
O1 C3 1.209(4) . ?
C3 C2 1.512(5) . ?
C15 O2 1.197(4) . ?
C15 C10 1.534(5) . ?
C11 N1 1.131(4) . ?
C11 C10 1.479(5) . ?
C1 C2 1.328(5) . ?
C1 C4 1.467(5) . ?
C4 C5 1.379(5) . ?
C4 C9 1.389(5) . ?
C2 C10 1.535(5) . ?
C19 C20 1.389(6) . ?
C10 C12 1.558(5) . ?
C9 C8 1.385(5) . ?
C7 C6 1.366(6) . ?
C7 C8 1.371(6) . ?
C12 C13 1.511(6) . ?
C12 C14 1.529(5) . ?
C6 C5 1.368(5) . ?
C21 C22 1.355(7) . ?
C21 C20 1.362(6) . ?
C23 C22 1.367(6) . ?
C16 C17 1.356(7) . ?

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
C15 O3 C16 114.9(4) . . ?
C19 C18 C23 118.3(4) . . ?
C19 C18 C3 122.9(4) . . ?
C23 C18 C3 118.8(4) . . ?
O1 C3 C18 120.7(3) . . ?
O1 C3 C2 120.4(4) . . ?
C18 C3 C2 118.9(4) . . ?
O2 C15 O3 124.7(4) . . ?
O2 C15 C10 120.9(4) . . ?
O3 C15 C10 114.4(4) . . ?
N1 C11 C10 175.8(4) . . ?
C2 C1 C4 128.0(3) . . ?
C5 C4 C9 118.3(4) . . ?
C5 C4 C1 118.9(3) . . ?
C9 C4 C1 122.8(4) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 C10 122.7(3) . . ?
C3 C2 C10 116.5(3) . . ?
C18 C19 C20 120.8(4) . . ?
C11 C10 C15 110.8(3) . . ?
C11 C10 C2 110.8(3) . . ?
C15 C10 C2 106.6(3) . . ?
C11 C10 C12 107.4(3) . . ?
C15 C10 C12 107.7(3) . . ?
C2 C10 C12 113.6(3) . . ?
C8 C9 C4 120.3(4) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 Br1 119.1(4) . . ?
C8 C7 Br1 119.3(4) . . ?
C13 C12 C14 111.9(4) . . ?
C13 C12 C10 111.6(3) . . ?
C14 C12 C10 111.1(3) . . ?
C7 C6 C5 118.6(4) . . ?
C22 C21 C20 121.5(5) . . ?
C22 C21 Cl1 119.8(4) . . ?
C20 C21 Cl1 118.6(5) . . ?
C7 C8 C9 119.2(4) . . ?
C6 C5 C4 122.0(4) . . ?
C22 C23 C18 120.8(4) . . ?
C21 C22 C23 119.9(4) . . ?
C21 C20 C19 118.7(5) . . ?
C17 C16 O3 109.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.045
