# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_BB2
_database_code_depnum_ccdc_archive 'CCDC 2082067'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 Br Cl N2 O'
_chemical_formula_sum            'C12 H8 Br Cl N2 O'
_chemical_formula_weight         311.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.4398(3)
_cell_length_b                   19.0129(11)
_cell_length_c                   13.8958(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.180(3)
_cell_angle_gamma                90
_cell_volume                     1172.14(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    250
_cell_measurement_temperature    149.59
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.288
_exptl_absorpt_coefficient_mu    3.717
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.757
_diffrn_reflns_theta_min         2.597
_diffrn_ambient_temperature      149.59
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1953
_reflns_number_total             2497
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.296
_refine_diff_density_min         -1.660
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1548
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C9(H9), C11(H11), C3(H3), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.00870(10) 0.38458(3) 0.49515(3) 0.0405(2) Uani 1 1 d . . . . .
Cl1 Cl 1.4243(3) 0.72307(6) 0.33714(8) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.4463(7) 0.44318(16) 0.0987(2) 0.0340(7) Uani 1 1 d . . . . .
H1 H 0.561252 0.478282 0.098974 0.051 Uiso 1 1 calc R U . . .
N2 N 0.7803(7) 0.54251(17) 0.1737(2) 0.0264(7) Uani 1 1 d . . . . .
N1 N 1.0948(8) 0.63066(18) 0.2443(2) 0.0268(7) Uani 1 1 d . . . . .
C6 C 0.3486(9) 0.4590(2) 0.3583(3) 0.0282(9) Uani 1 1 d . . . . .
H6 H 0.415555 0.486718 0.411860 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1476(9) 0.4056(2) 0.3709(3) 0.0294(9) Uani 1 1 d . . . . .
C8 C 0.9943(8) 0.5967(2) 0.1649(3) 0.0258(8) Uani 1 1 d . . . . .
C7 C 0.6714(8) 0.5287(2) 0.2561(3) 0.0260(8) Uani 1 1 d . . . . .
H7 H 0.733894 0.555796 0.310720 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3507(8) 0.4320(2) 0.1884(3) 0.0263(8) Uani 1 1 d . . . . .
C1 C 0.4563(9) 0.4729(2) 0.2667(3) 0.0260(8) Uani 1 1 d . . . . .
C4 C 0.0435(10) 0.3650(2) 0.2933(3) 0.0318(9) Uani 1 1 d . . . . .
H4 H -0.097738 0.328364 0.302783 0.038 Uiso 1 1 calc R U . . .
C9 C 1.0893(9) 0.6126(2) 0.0741(3) 0.0316(9) Uani 1 1 d . . . . .
H9 H 1.013861 0.587521 0.019246 0.038 Uiso 1 1 calc R U . . .
C11 C 1.4009(10) 0.7026(2) 0.1449(3) 0.0321(9) Uani 1 1 d . . . . .
H11 H 1.538945 0.740554 0.140324 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1464(9) 0.3781(2) 0.2019(3) 0.0300(9) Uani 1 1 d . . . . .
H3 H 0.077020 0.350235 0.148785 0.036 Uiso 1 1 calc R U . . .
C10 C 1.2971(10) 0.6660(2) 0.0653(3) 0.0349(9) Uani 1 1 d . . . . .
H10 H 1.368609 0.677522 0.003630 0.042 Uiso 1 1 calc R U . . .
C12 C 1.2926(9) 0.6811(2) 0.2323(3) 0.0297(9) 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 C5 1.898(4) . ?
Cl1 C12 1.743(4) . ?
O1 H1 0.8400 . ?
O1 C2 1.349(5) . ?
N2 C8 1.411(5) . ?
N2 C7 1.286(5) . ?
N1 C8 1.340(5) . ?
N1 C12 1.315(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.367(6) . ?
C6 C1 1.402(6) . ?
C5 C4 1.390(6) . ?
C8 C9 1.379(6) . ?
C7 H7 0.9500 . ?
C7 C1 1.438(6) . ?
C2 C1 1.404(5) . ?
C2 C3 1.385(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.372(6) . ?
C11 C12 1.385(6) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C7 N2 C8 120.2(3) . . ?
C12 N1 C8 116.7(4) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C1 120.2(4) . . ?
C1 C6 H6 119.9 . . ?
C6 C5 Br1 120.5(3) . . ?
C6 C5 C4 120.8(4) . . ?
C4 C5 Br1 118.6(3) . . ?
N1 C8 N2 119.0(3) . . ?
N1 C8 C9 123.0(4) . . ?
C9 C8 N2 118.0(4) . . ?
N2 C7 H7 119.5 . . ?
N2 C7 C1 121.0(4) . . ?
C1 C7 H7 119.5 . . ?
O1 C2 C1 121.4(4) . . ?
O1 C2 C3 118.2(4) . . ?
C3 C2 C1 120.4(4) . . ?
C6 C1 C7 118.9(4) . . ?
C6 C1 C2 118.9(4) . . ?
C2 C1 C7 122.2(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.0 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.1(4) . . ?
C10 C9 H9 120.9 . . ?
C10 C11 H11 121.9 . . ?
C10 C11 C12 116.1(4) . . ?
C12 C11 H11 121.9 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
N1 C12 Cl1 115.6(3) . . ?
N1 C12 C11 125.6(4) . . ?
C11 C12 Cl1 118.8(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
Br1 C5 C4 C3 -178.5(3) . . . . ?
O1 C2 C1 C6 179.9(4) . . . . ?
O1 C2 C1 C7 -0.2(6) . . . . ?
O1 C2 C3 C4 179.9(4) . . . . ?
N2 C8 C9 C10 179.5(4) . . . . ?
N2 C7 C1 C6 178.7(4) . . . . ?
N2 C7 C1 C2 -1.2(6) . . . . ?
N1 C8 C9 C10 -0.1(6) . . . . ?
C6 C5 C4 C3 0.7(6) . . . . ?
C5 C6 C1 C7 -179.0(4) . . . . ?
C5 C6 C1 C2 1.0(6) . . . . ?
C5 C4 C3 C2 -0.5(6) . . . . ?
C8 N2 C7 C1 -179.1(3) . . . . ?
C8 N1 C12 Cl1 -178.8(3) . . . . ?
C8 N1 C12 C11 1.2(6) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C7 N2 C8 N1 3.9(5) . . . . ?
C7 N2 C8 C9 -175.8(4) . . . . ?
C1 C6 C5 Br1 178.3(3) . . . . ?
C1 C6 C5 C4 -0.9(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C3 C2 C1 C6 -0.8(6) . . . . ?
C3 C2 C1 C7 179.2(4) . . . . ?
C10 C11 C12 Cl1 177.8(3) . . . . ?
C10 C11 C12 N1 -2.2(7) . . . . ?
C12 N1 C8 N2 -179.6(3) . . . . ?
C12 N1 C8 C9 0.0(6) . . . . ?
C12 C11 C10 C9 2.0(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BB1
_database_code_depnum_ccdc_archive 'CCDC 2082068'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_audit_creation_date             2020-12-17
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 Br Cl N2 O'
_chemical_formula_sum            'C12 H8 Br Cl N2 O'
_chemical_formula_weight         311.56
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   25.1344(12)
_cell_length_b                   3.87360(10)
_cell_length_c                   11.9831(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1166.68(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3657
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   0.623
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    3.735
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0520
0.00 0.00 -1.00 0.1170
0.00 1.00 0.00 0.1560
0.00 -1.00 0.00 0.1580
1.00 0.00 0.00 0.0710
-1.00 0.00 0.00 0.0050

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8638
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.770
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2170
_reflns_number_total             2444
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C7(H7), C11(H11), C6(H6), C10(H10), C9(H9)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.35514(2) -0.24316(9) 0.38085(7) 0.02585(10) Uani 1 1 d . . . . .
Cl1 Cl 0.71319(4) 0.4531(2) 0.27579(8) 0.0282(2) Uani 1 1 d . . . . .
N2 N 0.57180(13) 0.4582(8) 0.5673(3) 0.0199(7) Uani 1 1 d . . . . .
N1 N 0.64102(12) 0.4724(7) 0.4320(2) 0.0173(6) Uani 1 1 d . . . . .
O1 O 0.50101(12) 0.3855(8) 0.7237(2) 0.0311(6) Uani 1 1 d . . . . .
H1 H 0.529403 0.455508 0.694470 0.047 Uiso 1 1 calc R U . . .
C4 C 0.38532(17) -0.0034(10) 0.5958(3) 0.0276(9) Uani 1 1 d . . . . .
H4 H 0.350500 -0.073720 0.616636 0.033 Uiso 1 1 calc R U . . .
C3 C 0.41887(16) 0.1410(12) 0.6741(3) 0.0280(9) Uani 1 1 d . . . . .
H3 H 0.407130 0.167771 0.748934 0.034 Uiso 1 1 calc R U . . .
C2 C 0.46949(17) 0.2470(9) 0.6444(3) 0.0226(8) Uani 1 1 d . . . . .
C1 C 0.48706(15) 0.2054(9) 0.5330(3) 0.0178(8) Uani 1 1 d . . . . .
C7 C 0.53934(15) 0.3158(9) 0.4980(3) 0.0192(8) Uani 1 1 d . . . . .
H7 H 0.549960 0.282934 0.422620 0.023 Uiso 1 1 calc R U . . .
C8 C 0.62320(16) 0.5590(9) 0.5337(3) 0.0193(8) Uani 1 1 d . . . . .
C12 C 0.69024(15) 0.5687(8) 0.4083(3) 0.0196(8) Uani 1 1 d . . . . .
C11 C 0.72444(16) 0.7459(9) 0.4777(3) 0.0237(8) Uani 1 1 d . . . . .
H11 H 0.759602 0.804262 0.455534 0.028 Uiso 1 1 calc R U . . .
C5 C 0.40247(15) -0.0458(9) 0.4866(3) 0.0199(8) Uani 1 1 d . . . . .
C6 C 0.45233(15) 0.0578(9) 0.4547(3) 0.0180(8) Uani 1 1 d . . . . .
H6 H 0.463399 0.029717 0.379434 0.022 Uiso 1 1 calc R U . . .
C10 C 0.70441(17) 0.8339(9) 0.5818(3) 0.0246(9) Uani 1 1 d . . . . .
H10 H 0.725766 0.960595 0.632834 0.030 Uiso 1 1 calc R U . . .
C9 C 0.65382(16) 0.7379(9) 0.6111(3) 0.0236(8) Uani 1 1 d . . . . .
H9 H 0.639964 0.792341 0.682727 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.899(4) . ?
Cl1 C12 1.747(3) . ?
N2 C7 1.289(5) . ?
N2 C8 1.409(5) . ?
N1 C8 1.341(4) . ?
N1 C12 1.323(5) . ?
O1 H1 0.8400 . ?
O1 C2 1.349(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(6) . ?
C4 C5 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C2 1.384(6) . ?
C2 C1 1.415(5) . ?
C1 C7 1.444(5) . ?
C1 C6 1.404(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(5) . ?
C12 C11 1.379(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.389(6) . ?
C5 C6 1.370(5) . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.370(6) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C8 121.0(3) . . ?
C12 N1 C8 115.9(3) . . ?
C2 O1 H1 109.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.5(4) . . ?
C2 C3 H3 119.8 . . ?
O1 C2 C3 118.5(3) . . ?
O1 C2 C1 121.8(3) . . ?
C3 C2 C1 119.7(4) . . ?
C2 C1 C7 121.6(3) . . ?
C6 C1 C2 118.9(3) . . ?
C6 C1 C7 119.5(3) . . ?
N2 C7 C1 121.0(3) . . ?
N2 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
N1 C8 N2 119.8(3) . . ?
N1 C8 C9 123.1(4) . . ?
C9 C8 N2 117.0(3) . . ?
N1 C12 Cl1 115.6(3) . . ?
N1 C12 C11 126.4(3) . . ?
C11 C12 Cl1 118.0(3) . . ?
C12 C11 H11 122.0 . . ?
C12 C11 C10 116.0(4) . . ?
C10 C11 H11 122.0 . . ?
C4 C5 Br1 118.8(3) . . ?
C6 C5 Br1 120.3(3) . . ?
C6 C5 C4 120.9(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9 120.7 . . ?

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
Br1 C5 C6 C1 179.6(3) . . . . ?
Cl1 C12 C11 C10 179.7(3) . . . . ?
N2 C8 C9 C10 178.7(3) . . . . ?
N1 C8 C9 C10 0.7(5) . . . . ?
N1 C12 C11 C10 -0.9(5) . . . . ?
O1 C2 C1 C7 -1.3(5) . . . . ?
O1 C2 C1 C6 179.7(3) . . . . ?
C4 C3 C2 O1 -179.7(4) . . . . ?
C4 C3 C2 C1 -0.3(6) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C3 C4 C5 Br1 -179.7(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C2 C1 C7 179.3(3) . . . . ?
C3 C2 C1 C6 0.3(5) . . . . ?
C2 C1 C7 N2 -0.3(5) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C7 N2 C8 N1 -7.4(5) . . . . ?
C7 N2 C8 C9 174.5(3) . . . . ?
C7 C1 C6 C5 -179.5(3) . . . . ?
C8 N2 C7 C1 178.6(3) . . . . ?
C8 N1 C12 Cl1 179.7(2) . . . . ?
C8 N1 C12 C11 0.3(5) . . . . ?
C12 N1 C8 N2 -178.1(3) . . . . ?
C12 N1 C8 C9 -0.2(5) . . . . ?
C12 C11 C10 C9 1.4(5) . . . . ?
C11 C10 C9 C8 -1.3(5) . . . . ?
C5 C4 C3 C2 0.6(6) . . . . ?
C6 C1 C7 N2 178.7(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
