# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20190511zh_zy_liuli299_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1940471'
loop_
_audit_author_name
_audit_author_address
'Li Liu'
;Changzhou University
China
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-13 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         ?
_chemical_formula_sum            'C25 H20 Cl N3 O'
_chemical_formula_weight         413.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   31.8664(15)
_cell_length_b                   8.9719(5)
_cell_length_c                   16.6944(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.086(2)
_cell_angle_gamma                90
_cell_volume                     4482.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2136
_cell_measurement_theta_min      0.812
_cell_measurement_theta_max      0.887

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.093
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16088
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.569
_diffrn_reflns_theta_max         53.950
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4082
_reflns_number_gt                2767
_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.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)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_number_reflns         4082
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2585
_refine_ls_wR_factor_gt          0.2214
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_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_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
Cl01 Cl 0.71133(3) 0.88957(11) 0.39936(6) 0.0658(4) Uani 1 1 d . . . . .
N002 N 0.57746(7) 0.4326(3) 0.48791(14) 0.0393(6) Uani 1 1 d . . . . .
O003 O 0.77023(7) 0.1571(3) 0.67409(15) 0.0610(7) Uani 1 1 d . . . . .
N004 N 0.55249(8) 0.5078(3) 0.34323(15) 0.0474(7) Uani 1 1 d . . . . .
N005 N 0.47004(8) 0.3609(3) 0.31948(17) 0.0496(7) Uani 1 1 d . . . . .
H005 H 0.468508 0.407941 0.272299 0.060 Uiso 1 1 calc R U . . .
C006 C 0.54735(9) 0.4384(4) 0.40771(18) 0.0387(7) Uani 1 1 d . . . . .
C007 C 0.61900(9) 0.5194(3) 0.51535(17) 0.0382(7) Uani 1 1 d . . . . .
H007 H 0.617278 0.592880 0.559173 0.046 Uiso 1 1 calc R U . . .
C008 C 0.66596(10) 0.2929(4) 0.51575(19) 0.0446(8) Uani 1 1 d . . . . .
H008 H 0.645198 0.267041 0.461395 0.054 Uiso 1 1 calc R U . . .
C009 C 0.70314(10) 0.2026(4) 0.5528(2) 0.0465(8) Uani 1 1 d . . . . .
H009 H 0.708037 0.117209 0.523549 0.056 Uiso 1 1 calc R U . . .
C00A C 0.62355(9) 0.6062(3) 0.44051(18) 0.0381(7) Uani 1 1 d . . . . .
C00B C 0.65867(9) 0.4192(3) 0.55641(18) 0.0366(7) Uani 1 1 d . . . . .
C00C C 0.50623(10) 0.3583(4) 0.39493(19) 0.0422(8) Uani 1 1 d . . . . .
C00D C 0.73265(9) 0.2383(4) 0.63217(19) 0.0447(8) Uani 1 1 d . . . . .
C00E C 0.49699(10) 0.2729(4) 0.45449(19) 0.0428(8) Uani 1 1 d . . . . .
C00F C 0.66024(10) 0.6991(4) 0.45273(19) 0.0442(8) Uani 1 1 d . . . . .
H00F H 0.682197 0.709061 0.507865 0.053 Uiso 1 1 calc R U . . .
C00G C 0.66470(10) 0.7765(4) 0.3847(2) 0.0488(8) Uani 1 1 d . . . . .
C00H C 0.59148(10) 0.5944(4) 0.35968(19) 0.0446(8) Uani 1 1 d . . . . .
C00I C 0.68903(10) 0.4519(4) 0.63670(19) 0.0457(8) Uani 1 1 d . . . . .
H00I H 0.684512 0.537509 0.666244 0.055 Uiso 1 1 calc R U . . .
C00J C 0.45258(10) 0.2187(3) 0.4164(2) 0.0437(8) Uani 1 1 d . . . . .
C00K C 0.42405(11) 0.1299(4) 0.4442(3) 0.0547(9) Uani 1 1 d . . . . .
H00K H 0.433750 0.091413 0.500617 0.066 Uiso 1 1 calc R U . . .
C00L C 0.43687(10) 0.2758(4) 0.3323(2) 0.0482(8) Uani 1 1 d . . . . .
C00M C 0.72566(10) 0.3620(4) 0.6742(2) 0.0525(9) Uani 1 1 d . . . . .
H00M H 0.746086 0.385815 0.729206 0.063 Uiso 1 1 calc R U . . .
C00N C 0.36681(11) 0.1575(4) 0.3056(3) 0.0619(10) Uani 1 1 d . . . . .
H00N H 0.337337 0.135257 0.268847 0.074 Uiso 1 1 calc R U . . .
C00O C 0.63348(11) 0.7648(4) 0.3039(2) 0.0556(9) Uani 1 1 d . . . . .
H00O H 0.637076 0.817994 0.257497 0.067 Uiso 1 1 calc R U . . .
C00P C 0.53189(11) 0.2525(4) 0.5409(2) 0.0549(9) Uani 1 1 d . . . . .
H00A H 0.517553 0.252163 0.584888 0.066 Uiso 1 1 calc R U . . .
H00B H 0.547008 0.155352 0.543158 0.066 Uiso 1 1 calc R U . . .
C00Q C 0.38180(12) 0.0994(4) 0.3885(3) 0.0604(10) Uani 1 1 d . . . . .
H00Q H 0.362476 0.037929 0.406555 0.072 Uiso 1 1 calc R U . . .
C00R C 0.56556(12) 0.3753(5) 0.5589(2) 0.0615(11) Uani 1 1 d . . . . .
H00C H 0.554166 0.459683 0.583703 0.074 Uiso 1 1 calc R U . . .
H00D H 0.593274 0.339719 0.603143 0.074 Uiso 1 1 calc R U . . .
C00S C 0.39341(10) 0.2453(5) 0.2761(2) 0.0562(9) Uani 1 1 d . . . . .
H00S H 0.382955 0.284341 0.219821 0.067 Uiso 1 1 calc R U . . .
C00T C 0.59678(11) 0.6738(4) 0.2919(2) 0.0548(9) Uani 1 1 d . . . . .
H00T H 0.574831 0.665313 0.236671 0.066 Uiso 1 1 calc R U . . .
C00U C 0.78062(12) 0.0351(5) 0.6308(2) 0.0658(11) Uani 1 1 d . . . . .
H00E H 0.756631 -0.039042 0.618223 0.099 Uiso 1 1 calc R U . . .
H00G H 0.808780 -0.010097 0.666803 0.099 Uiso 1 1 calc R U . . .
H00H H 0.783647 0.069730 0.577398 0.099 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
Cl01 C00G 1.746(3) . ?
N002 C006 1.354(3) . ?
N002 C00R 1.456(4) . ?
N002 C007 1.467(4) . ?
O003 C00D 1.371(3) . ?
O003 C00U 1.412(5) . ?
N004 C006 1.302(4) . ?
N004 C00H 1.410(4) . ?
N005 C00L 1.379(4) . ?
N005 C00C 1.385(4) . ?
N005 H005 0.8800 . ?
C006 C00C 1.445(4) . ?
C007 C00A 1.521(4) . ?
C007 C00B 1.511(4) . ?
C007 H007 1.0000 . ?
C008 C00B 1.381(4) . ?
C008 C009 1.392(4) . ?
C008 H008 0.9500 . ?
C009 C00D 1.373(4) . ?
C009 H009 0.9500 . ?
C00A C00H 1.389(4) . ?
C00A C00F 1.392(4) . ?
C00B C00I 1.389(4) . ?
C00C C00E 1.365(5) . ?
C00D C00M 1.371(5) . ?
C00E C00J 1.423(4) . ?
C00E C00P 1.499(4) . ?
C00F C00G 1.379(5) . ?
C00F H00F 0.9500 . ?
C00G C00O 1.378(4) . ?
C00H C00T 1.396(5) . ?
C00I C00M 1.380(4) . ?
C00I H00I 0.9500 . ?
C00J C00K 1.402(5) . ?
C00J C00L 1.415(4) . ?
C00K C00Q 1.376(5) . ?
C00K H00K 0.9500 . ?
C00L C00S 1.407(4) . ?
C00M H00M 0.9500 . ?
C00N C00S 1.367(5) . ?
C00N C00Q 1.400(5) . ?
C00N H00N 0.9500 . ?
C00O C00T 1.383(5) . ?
C00O H00O 0.9500 . ?
C00P C00R 1.495(5) . ?
C00P H00A 0.9900 . ?
C00P H00B 0.9900 . ?
C00Q H00Q 0.9500 . ?
C00R H00C 0.9900 . ?
C00R H00D 0.9900 . ?
C00S H00S 0.9500 . ?
C00T H00T 0.9500 . ?
C00U H00E 0.9800 . ?
C00U H00G 0.9800 . ?
C00U H00H 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 N002 C00R 121.6(3) . . ?
C006 N002 C007 123.0(3) . . ?
C00R N002 C007 113.1(2) . . ?
C00D O003 C00U 117.9(2) . . ?
C006 N004 C00H 117.1(2) . . ?
C00L N005 C00C 107.0(3) . . ?
C00L N005 H005 126.5 . . ?
C00C N005 H005 126.5 . . ?
N004 C006 N002 126.1(3) . . ?
N004 C006 C00C 118.8(3) . . ?
N002 C006 C00C 115.2(3) . . ?
N002 C007 C00A 110.2(2) . . ?
N002 C007 C00B 110.5(2) . . ?
C00A C007 C00B 112.1(2) . . ?
N002 C007 H007 107.9 . . ?
C00A C007 H007 107.9 . . ?
C00B C007 H007 107.9 . . ?
C00B C008 C009 121.3(3) . . ?
C00B C008 H008 119.3 . . ?
C009 C008 H008 119.3 . . ?
C00D C009 C008 119.3(3) . . ?
C00D C009 H009 120.4 . . ?
C008 C009 H009 120.4 . . ?
C00H C00A C00F 119.3(3) . . ?
C00H C00A C007 120.9(3) . . ?
C00F C00A C007 119.9(3) . . ?
C008 C00B C00I 118.0(3) . . ?
C008 C00B C007 121.4(2) . . ?
C00I C00B C007 120.6(3) . . ?
C00E C00C N005 110.6(3) . . ?
C00E C00C C006 125.7(3) . . ?
N005 C00C C006 123.7(3) . . ?
O003 C00D C00M 115.8(3) . . ?
O003 C00D C009 123.9(3) . . ?
C00M C00D C009 120.3(3) . . ?
C00C C00E C00J 107.3(3) . . ?
C00C C00E C00P 119.6(3) . . ?
C00J C00E C00P 133.1(3) . . ?
C00G C00F C00A 120.0(3) . . ?
C00G C00F H00F 120.0 . . ?
C00A C00F H00F 120.0 . . ?
C00F C00G C00O 121.6(3) . . ?
C00F C00G Cl01 120.0(2) . . ?
C00O C00G Cl01 118.4(3) . . ?
C00A C00H N004 122.5(3) . . ?
C00A C00H C00T 119.7(3) . . ?
N004 C00H C00T 117.9(3) . . ?
C00B C00I C00M 121.0(3) . . ?
C00B C00I H00I 119.5 . . ?
C00M C00I H00I 119.5 . . ?
C00K C00J C00E 134.8(3) . . ?
C00K C00J C00L 119.0(3) . . ?
C00E C00J C00L 106.1(3) . . ?
C00Q C00K C00J 119.0(4) . . ?
C00Q C00K H00K 120.5 . . ?
C00J C00K H00K 120.5 . . ?
N005 C00L C00S 129.5(3) . . ?
N005 C00L C00J 109.0(3) . . ?
C00S C00L C00J 121.5(3) . . ?
C00D C00M C00I 120.1(3) . . ?
C00D C00M H00M 119.9 . . ?
C00I C00M H00M 119.9 . . ?
C00S C00N C00Q 121.8(3) . . ?
C00S C00N H00N 119.1 . . ?
C00Q C00N H00N 119.1 . . ?
C00T C00O C00G 118.5(3) . . ?
C00T C00O H00O 120.8 . . ?
C00G C00O H00O 120.8 . . ?
C00R C00P C00E 110.3(3) . . ?
C00R C00P H00A 109.6 . . ?
C00E C00P H00A 109.6 . . ?
C00R C00P H00B 109.6 . . ?
C00E C00P H00B 109.6 . . ?
H00A C00P H00B 108.1 . . ?
C00K C00Q C00N 121.1(4) . . ?
C00K C00Q H00Q 119.4 . . ?
C00N C00Q H00Q 119.4 . . ?
N002 C00R C00P 117.8(3) . . ?
N002 C00R H00C 107.9 . . ?
C00P C00R H00C 107.9 . . ?
N002 C00R H00D 107.9 . . ?
C00P C00R H00D 107.9 . . ?
H00C C00R H00D 107.2 . . ?
C00N C00S C00L 117.5(3) . . ?
C00N C00S H00S 121.2 . . ?
C00L C00S H00S 121.2 . . ?
C00O C00T C00H 121.0(3) . . ?
C00O C00T H00T 119.5 . . ?
C00H C00T H00T 119.5 . . ?
O003 C00U H00E 109.5 . . ?
O003 C00U H00G 109.5 . . ?
H00E C00U H00G 109.5 . . ?
O003 C00U H00H 109.5 . . ?
H00E C00U H00H 109.5 . . ?
H00G C00U H00H 109.5 . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_201900723ZH_LIULI_SBS_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1943441'
loop_
_audit_author_name
_audit_author_address
'Li Liu'
;Changzhou University
China
;
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2019-09-13 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         ?
_chemical_formula_sum            'C24 H20 Br Cl N2 O2'
_chemical_formula_weight         483.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9338 1.0006 '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                   11.4651(6)
_cell_length_b                   10.5710(5)
_cell_length_c                   17.7266(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.480(2)
_cell_angle_gamma                90
_cell_volume                     2070.48(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      54.01

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.703
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16566
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.605
_diffrn_reflns_theta_max         54.028
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3782
_reflns_number_gt                3644
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0600P)²+2.6738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12812(3) -0.16913(3) 0.57674(2) 0.04994(16) Uani 1 1 d . . . . .
C1 C 0.8428(3) 0.5404(3) 0.4794(2) 0.0495(8) Uani 1 1 d . . . . .
H1A H 0.840575 0.469864 0.513961 0.074 Uiso 1 1 calc R U . . .
H1B H 0.909716 0.595779 0.503778 0.074 Uiso 1 1 calc R U . . .
H1C H 0.853369 0.508917 0.430270 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4311(3) 0.8150(3) 0.4354(2) 0.0518(9) Uani 1 1 d . . . . .
H2A H 0.391059 0.813056 0.379849 0.078 Uiso 1 1 calc R U . . .
H2B H 0.453806 0.901280 0.451403 0.078 Uiso 1 1 calc R U . . .
H2C H 0.376531 0.783059 0.464420 0.078 Uiso 1 1 calc R U . . .
C3 C 0.6284(3) 0.5468(3) 0.43112(16) 0.0323(6) Uani 1 1 d . . . . .
C4 C 0.6217(3) 0.4247(3) 0.40236(17) 0.0359(6) Uani 1 1 d . . . . .
H4 H 0.693351 0.380094 0.404212 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5100(3) 0.3670(3) 0.37060(16) 0.0328(6) Uani 1 1 d . . . . .
C6 C 0.5003(3) 0.2376(3) 0.3338(2) 0.0504(8) Uani 1 1 d . . . . .
H6A H 0.498446 0.246224 0.278429 0.060 Uiso 1 1 calc R U . . .
H6B H 0.571992 0.187923 0.359542 0.060 Uiso 1 1 calc R U . . .
C7 C 0.3930(3) 0.1710(3) 0.3399(3) 0.0524(9) Uani 1 1 d . . . . .
H7A H 0.405912 0.140780 0.393742 0.063 Uiso 1 1 calc R U . . .
H7B H 0.381393 0.096721 0.305598 0.063 Uiso 1 1 calc R U . . .
C8 C 0.2844(2) 0.3734(2) 0.33898(14) 0.0271(5) Uani 1 1 d . . . . .
C9 C 0.4042(2) 0.4321(2) 0.36905(14) 0.0268(5) Uani 1 1 d . . . . .
C10 C 0.4110(2) 0.5579(2) 0.39615(15) 0.0281(5) Uani 1 1 d . . . . .
H10 H 0.339460 0.602794 0.394151 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5211(2) 0.6156(2) 0.42545(15) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.2062(3) 0.1275(3) 0.44689(16) 0.0345(6) Uani 1 1 d . . . . .
H12 H 0.240773 0.208335 0.457505 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1971(3) 0.0508(3) 0.50828(17) 0.0393(7) Uani 1 1 d . . . . .
H13 H 0.225721 0.078819 0.560293 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1454(2) -0.0676(3) 0.49196(17) 0.0341(6) Uani 1 1 d . . . . .
C15 C 0.1042(3) -0.1103(3) 0.41653(18) 0.0412(7) Uani 1 1 d . . . . .
H15 H 0.068812 -0.190909 0.406296 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1153(3) -0.0330(3) 0.35521(17) 0.0387(7) Uani 1 1 d . . . . .
H16 H 0.088951 -0.062456 0.303401 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1650(2) 0.0871(2) 0.36994(15) 0.0273(5) Uani 1 1 d . . . . .
C18 C 0.1691(3) 0.1743(2) 0.30209(16) 0.0293(6) Uani 1 1 d . . . . .
H18 H 0.165753 0.120955 0.255657 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0603(2) 0.2619(2) 0.28232(14) 0.0285(5) Uani 1 1 d . . . . .
C20 C 0.0768(2) 0.3902(3) 0.30106(15) 0.0303(5) Uani 1 1 d . . . . .
C21 C -0.0245(3) 0.4687(3) 0.28742(18) 0.0384(6) Uani 1 1 d . . . . .
H21 H -0.014346 0.554645 0.301148 0.046 Uiso 1 1 calc R U . . .
C22 C -0.1392(3) 0.4228(3) 0.25425(18) 0.0395(7) Uani 1 1 d . . . . .
H22 H -0.206839 0.476623 0.244840 0.047 Uiso 1 1 calc R U . . .
C23 C -0.1528(3) 0.2962(3) 0.23515(16) 0.0343(6) Uani 1 1 d . . . . .
C24 C -0.0545(3) 0.2148(3) 0.24876(16) 0.0334(6) Uani 1 1 d . . . . .
H24 H -0.065606 0.128754 0.235368 0.040 Uiso 1 1 calc R U . . .
Cl1 Cl -0.29776(7) 0.23787(8) 0.19381(5) 0.0503(2) Uani 1 1 d . . . . .
N1 N 0.2813(2) 0.2484(2) 0.31882(13) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.1900(2) 0.4450(2) 0.33201(14) 0.0332(5) Uani 1 1 d . . . . .
O1 O 0.73196(18) 0.6093(2) 0.46498(13) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.53664(18) 0.73799(18) 0.45107(13) 0.0387(5) 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 C14 1.900(3) . ?
C1 O1 1.427(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O2 1.423(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 O1 1.350(3) . ?
C3 C4 1.382(4) . ?
C3 C11 1.410(4) . ?
C4 C5 1.395(4) . ?
C4 H4 0.9400 . ?
C5 C9 1.388(4) . ?
C5 C6 1.507(4) . ?
C6 C7 1.446(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 N1 1.481(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 N2 1.299(3) . ?
C8 N1 1.367(3) . ?
C8 C9 1.472(4) . ?
C9 C10 1.410(4) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9400 . ?
C11 O2 1.367(3) . ?
C12 C13 1.383(4) . ?
C12 C17 1.386(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.370(4) . ?
C15 C16 1.393(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.526(4) . ?
C18 N1 1.468(3) . ?
C18 C19 1.517(4) . ?
C18 H18 0.9900 . ?
C19 C24 1.384(4) . ?
C19 C20 1.397(4) . ?
C20 N2 1.393(4) . ?
C20 C21 1.395(4) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.388(4) . ?
C23 Cl1 1.740(3) . ?
C24 H24 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 C4 125.2(3) . . ?
O1 C3 C11 115.3(2) . . ?
C4 C3 C11 119.6(3) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C9 C5 C4 119.6(3) . . ?
C9 C5 C6 118.6(3) . . ?
C4 C5 C6 121.7(3) . . ?
C7 C6 C5 112.1(3) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 N1 114.1(3) . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 N1 125.2(2) . . ?
N2 C8 C9 117.5(2) . . ?
N1 C8 C9 117.3(2) . . ?
C5 C9 C10 119.5(2) . . ?
C5 C9 C8 121.6(2) . . ?
C10 C9 C8 118.8(2) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O2 C11 C10 124.8(2) . . ?
O2 C11 C3 115.5(2) . . ?
C10 C11 C3 119.7(2) . . ?
C13 C12 C17 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C17 C12 H12 119.4 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 Br1 120.2(2) . . ?
C13 C14 Br1 118.4(2) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C12 C17 C16 118.8(3) . . ?
C12 C17 C18 121.1(2) . . ?
C16 C17 C18 120.1(2) . . ?
N1 C18 C19 110.0(2) . . ?
N1 C18 C17 111.9(2) . . ?
C19 C18 C17 110.8(2) . . ?
N1 C18 H18 108.0 . . ?
C19 C18 H18 108.0 . . ?
C17 C18 H18 108.0 . . ?
C24 C19 C20 120.3(3) . . ?
C24 C19 C18 120.5(2) . . ?
C20 C19 C18 119.1(2) . . ?
N2 C20 C21 117.8(2) . . ?
N2 C20 C19 123.4(2) . . ?
C21 C20 C19 118.8(3) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 118.6(3) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C24 121.7(3) . . ?
C22 C23 Cl1 118.7(2) . . ?
C24 C23 Cl1 119.6(2) . . ?
C19 C24 C23 119.1(3) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C8 N1 C18 121.9(2) . . ?
C8 N1 C7 120.5(2) . . ?
C18 N1 C7 114.1(2) . . ?
C8 N2 C20 117.4(2) . . ?
C3 O1 C1 117.7(2) . . ?
C11 O2 C2 116.6(2) . . ?

_refine_diff_density_max         1.152
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.067

