# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2010167490
_database_code_depnum_ccdc_archive 'CCDC 2064258'
loop_
_audit_author_name
_audit_author_address
Yuan
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 Br Cl N O'
_chemical_formula_sum            'C11 H11 Br Cl N O'
_chemical_formula_weight         288.57
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.7336(5)
_cell_length_b                   9.4426(5)
_cell_length_c                   12.9051(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1186.11(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4662
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.868
_cell_measurement_theta_min      2.980
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    4.460
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1265 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.6405. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5057
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.844
_diffrn_reflns_theta_min         5.679
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.657
_reflns_number_gt                1823
_reflns_number_total             1866
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.2396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77952(4) 0.48281(4) 0.36031(5) 0.04108(17) Uani 1 1 d . . . . .
Cl1 Cl 0.60058(11) 0.80706(11) 0.68666(9) 0.0475(3) Uani 1 1 d . . . . .
O1 O 0.7687(2) -0.0638(3) 0.4140(3) 0.0406(7) Uani 1 1 d . . . . .
N1 N 0.5419(3) -0.0328(3) 0.3869(3) 0.0337(9) Uani 1 1 d . . . . .
H1 H 0.467497 0.014958 0.403599 0.040 Uiso 1 1 calc R . . . .
C1 C 0.6687(4) 0.5027(4) 0.4809(3) 0.0297(8) Uani 1 1 d . . . . .
C2 C 0.6719(4) 0.6324(4) 0.5307(3) 0.0327(8) Uani 1 1 d . . . . .
H2 H 0.726263 0.708113 0.504924 0.039 Uiso 1 1 calc R . . . .
C3 C 0.5935(4) 0.6481(4) 0.6191(3) 0.0314(8) Uani 1 1 d . . . . .
C4 C 0.5110(4) 0.5399(5) 0.6559(4) 0.0367(9) Uani 1 1 d . . . . .
H4 H 0.455434 0.553363 0.715603 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5109(4) 0.4116(4) 0.6038(4) 0.0345(9) Uani 1 1 d . . . . .
H5 H 0.454790 0.336877 0.629046 0.041 Uiso 1 1 calc R . . . .
C6 C 0.5904(4) 0.3887(4) 0.5158(3) 0.0294(8) Uani 1 1 d . . . . .
C7 C 0.5891(4) 0.2492(4) 0.4617(3) 0.0331(8) Uani 1 1 d . . . . .
H7 H 0.530762 0.238573 0.403227 0.040 Uiso 1 1 calc R . . . .
C8 C 0.6645(3) 0.1394(4) 0.4904(3) 0.0302(8) Uani 1 1 d . . . . .
C9 C 0.6626(4) 0.0058(4) 0.4276(4) 0.0313(9) Uani 1 1 d . . . . .
C10 C 0.7663(5) 0.1430(5) 0.5772(4) 0.0511(13) Uani 1 1 d . . . . .
H10A H 0.743137 0.069705 0.628084 0.077 Uiso 1 1 calc GR . . . .
H10B H 0.763915 0.236123 0.610618 0.077 Uiso 1 1 calc GR . . . .
H10C H 0.858645 0.125329 0.549782 0.077 Uiso 1 1 calc GR . . . .
C11 C 0.5303(4) -0.1517(5) 0.3156(4) 0.0440(10) Uani 1 1 d . . . . .
H11A H 0.547407 -0.118973 0.244715 0.066 Uiso 1 1 calc GR . . . .
H11B H 0.437684 -0.191962 0.320060 0.066 Uiso 1 1 calc GR . . . .
H11C H 0.598009 -0.224263 0.334080 0.066 Uiso 1 1 calc GR . . . .


_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 C1 1.903(4) . ?
Cl1 C3 1.737(4) . ?
O1 C9 1.236(5) . ?
N1 H1 0.8800 . ?
N1 C9 1.338(5) . ?
N1 C11 1.456(5) . ?
C1 C2 1.383(6) . ?
C1 C6 1.394(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(6) . ?
C3 C4 1.383(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(6) . ?
C6 C7 1.490(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.323(5) . ?
C8 C9 1.500(5) . ?
C8 C10 1.497(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C9 N1 H1 119.1 . . ?
C9 N1 C11 121.8(3) . . ?
C11 N1 H1 119.1 . . ?
C2 C1 Br1 117.0(3) . . ?
C2 C1 C6 123.1(4) . . ?
C6 C1 Br1 119.8(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 Cl1 119.1(3) . . ?
C2 C3 C4 121.6(4) . . ?
C4 C3 Cl1 119.3(3) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(4) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.1(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C7 122.4(4) . . ?
C5 C6 C1 116.6(4) . . ?
C5 C6 C7 121.0(4) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 C6 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 C10 124.0(4) . . ?
C10 C8 C9 115.5(3) . . ?
O1 C9 N1 122.2(4) . . ?
O1 C9 C8 120.9(4) . . ?
N1 C9 C8 116.9(3) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
