# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_s1
_audit_block_doi                 10.5517/ccdc.csd.cc261grh
_database_code_depnum_ccdc_archive 'CCDC 2027206'
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl2 N2'
_chemical_formula_sum            'C16 H14 Cl2 N2'
_chemical_formula_weight         305.19
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.3766(3)
_cell_length_b                   8.7055(5)
_cell_length_c                   15.6819(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.722(2)
_cell_angle_gamma                90
_cell_volume                     723.47(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.628
_shelx_estimated_absorpt_T_min   0.427
_exptl_absorpt_coefficient_mu    3.946
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12417
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.432
_diffrn_reflns_theta_min         5.725
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1426
_reflns_number_total             1432
_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       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_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         0.296
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.057
_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)+(0.0298P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
Cl1 Cl 0.88294(5) 0.61402(3) 0.90764(2) 0.02203(12) Uani 1 1 d . . . . .
N1 N 0.09372(17) 0.49792(11) 0.53718(6) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.4482(2) 0.70982(14) 0.80944(7) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.423899 0.770119 0.857853 0.021 Uiso 1 1 calc R . . . .
C3 C 0.2725(2) 0.71278(13) 0.73332(7) 0.0167(2) Uani 1 1 d . . . . .
H3 H 0.128948 0.777634 0.729632 0.020 Uiso 1 1 calc R . . . .
C6 C 0.6976(2) 0.52813(14) 0.74325(8) 0.0183(2) Uani 1 1 d . . . . .
H6 H 0.844682 0.466390 0.746773 0.022 Uiso 1 1 calc R . . . .
C4 C 0.3030(2) 0.62215(12) 0.66211(7) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.5186(2) 0.53019(13) 0.66805(7) 0.0168(2) Uani 1 1 d . . . . .
H5 H 0.543103 0.468501 0.620180 0.020 Uiso 1 1 calc R . . . .
C7 C 0.1079(2) 0.62214(13) 0.58256(7) 0.0148(2) Uani 1 1 d . . . . .
C8 C -0.0548(2) 0.76229(14) 0.56335(7) 0.0197(3) Uani 1 1 d . . . . .
H8A H -0.151159 0.754977 0.504583 0.030 Uiso 1 1 calc GR . . . .
H8B H 0.052076 0.854115 0.568008 0.030 Uiso 1 1 calc GR . . . .
H8C H -0.171519 0.769244 0.604914 0.030 Uiso 1 1 calc GR . . . .
C1 C 0.6585(2) 0.61753(13) 0.81318(7) 0.0164(2) 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
Cl1 C1 1.7457(12) . ?
N1 N1 1.4071(18) 3_566 ?
N1 C7 1.2897(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3920(16) . ?
C2 C1 1.3802(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3993(16) . ?
C6 H6 0.9500 . ?
C6 C5 1.3906(16) . ?
C6 C1 1.3893(17) . ?
C4 C5 1.3993(16) . ?
C4 C7 1.4881(15) . ?
C5 H5 0.9500 . ?
C7 C8 1.5018(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C7 N1 N1 113.77(11) . 3_566 ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.67(11) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.33(11) . . ?
C4 C3 H3 119.3 . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C1 C6 C5 119.14(11) . . ?
C3 C4 C7 120.53(10) . . ?
C5 C4 C3 118.48(11) . . ?
C5 C4 C7 120.98(10) . . ?
C6 C5 C4 120.72(11) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N1 C7 C4 115.48(10) . . ?
N1 C7 C8 126.33(10) . . ?
C4 C7 C8 118.19(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C1 Cl1 119.35(9) . . ?
C2 C1 C6 121.64(11) . . ?
C6 C1 Cl1 119.00(9) . . ?

_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_s1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2dzsqx
_database_code_depnum_ccdc_archive 'CCDC 2234130'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2022-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        '4-Bromoacetophenone azine'
_chemical_formula_moiety         'C16 H14 Br2 N2'
_chemical_formula_sum            'C16 H14 Br2 N2'
_chemical_formula_weight         394.11
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.5678(2)
_cell_length_b                   8.7473(4)
_cell_length_c                   15.6491(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.8027(14)
_cell_angle_gamma                90
_cell_volume                     753.18(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.00
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    6.743
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12187
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.211
_diffrn_reflns_theta_min         5.722
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1510
_reflns_number_total             1516
_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       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.119
_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)+(0.0281P)²+0.5021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.11369(3) 0.88376(2) 0.09354(2) 0.02986(10) Uani 1 1 d . . . . .
C4 C 0.7030(3) 0.87592(17) 0.34123(11) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.9080(3) 1.00135(16) 0.46380(9) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.3530(3) 0.87968(18) 0.19398(11) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.7284(3) 0.7857(2) 0.26956(11) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.866503 0.721233 0.271556 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3186(3) 0.9680(2) 0.26485(12) 0.0253(4) Uani 1 1 d . . . . .
H6 H 0.176412 1.028635 0.263279 0.030 Uiso 1 1 calc R . . . .
C2 C 0.5555(3) 0.7884(2) 0.19527(11) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.576510 0.728389 0.146341 0.029 Uiso 1 1 calc R . . . .
C5 C 0.4944(3) 0.96654(19) 0.33802(11) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.473106 1.027710 0.386455 0.028 Uiso 1 1 calc R . . . .
C7 C 0.8940(3) 0.87751(18) 0.41864(11) 0.0202(3) Uani 1 1 d . . . . .
C8 C 1.0546(3) 0.7398(2) 0.43637(11) 0.0268(4) Uani 1 1 d . . . . .
H8A H 0.954557 0.647060 0.430538 0.040 Uiso 1 1 calc GR . . . .
H8B H 1.144273 0.745893 0.495242 0.040 Uiso 1 1 calc GR . . . .
H8C H 1.169697 0.736387 0.394893 0.040 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 1.8992(18) . ?
C4 C3 1.396(2) . ?
C4 C5 1.400(2) . ?
C4 C7 1.485(2) . ?
N1 N1 1.407(3) 3_776 ?
N1 C7 1.289(2) . ?
C1 C6 1.389(3) . ?
C1 C2 1.379(3) . ?
C3 C2 1.392(2) . ?
C6 C5 1.388(2) . ?
C7 C8 1.501(2) . ?

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 C4 C5 118.47(16) . . ?
C3 C4 C7 120.83(15) . . ?
C5 C4 C7 120.69(15) . . ?
C7 N1 N1 113.77(17) . 3_776 ?
C6 C1 Br1 119.03(13) . . ?
C2 C1 Br1 119.43(13) . . ?
C2 C1 C6 121.54(16) . . ?
C2 C3 C4 121.28(16) . . ?
C5 C6 C1 119.17(16) . . ?
C1 C2 C3 118.77(16) . . ?
C6 C5 C4 120.74(16) . . ?
C4 C7 C8 118.38(14) . . ?
N1 C7 C4 115.52(14) . . ?
N1 C7 C8 126.09(16) . . ?

_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_s1_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc2fkqzq
_database_code_depnum_ccdc_archive 'CCDC 2251374'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-03-23 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        '4-chloroacetophenone azine'
_chemical_formula_moiety         'C16 H14 Cl2 N2'
_chemical_formula_sum            'C16 H14 Cl2 N2'
_chemical_formula_weight         305.19
_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'
Cl Cl 0.1484 0.1585 '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                   15.0686(6)
_cell_length_b                   9.1426(4)
_cell_length_c                   10.3068(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.7551(13)
_cell_angle_gamma                90
_cell_volume                     1416.88(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9437.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.512
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3633
_reflns_number_total             4325
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.138
_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)+(0.0174P)²+1.8103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_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
Cl1 Cl -0.04096(3) 0.39902(5) 0.26398(4) 0.02560(11) Uani 1 1 d . . . . .
Cl2 Cl 0.82728(2) 0.39000(5) 0.99365(4) 0.01931(9) Uani 1 1 d . . . . .
N1 N 0.35878(8) 0.41501(15) 0.57818(12) 0.0140(2) Uani 1 1 d . . . . .
N2 N 0.43399(8) 0.41793(15) 0.66476(12) 0.0137(2) Uani 1 1 d . . . . .
C1 C 0.05303(10) 0.39492(19) 0.37170(15) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.05790(11) 0.2941(2) 0.47208(16) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.0099(14) 0.228(2) 0.482(2) 0.024 Uiso 1 1 d R . . . .
C3 C 0.13306(10) 0.29185(18) 0.55746(16) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.1373(13) 0.224(2) 0.627(2) 0.021 Uiso 1 1 d R . . . .
C4 C 0.20401(9) 0.38729(17) 0.54077(14) 0.0124(3) Uani 1 1 d . . . . .
C5 C 0.19719(10) 0.48776(17) 0.43821(15) 0.0149(3) Uani 1 1 d . . . . .
H5 H 0.2447(13) 0.554(2) 0.4265(19) 0.018 Uiso 1 1 d R . . . .
C6 C 0.12136(10) 0.49362(19) 0.35424(15) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.1150(13) 0.563(2) 0.287(2) 0.021 Uiso 1 1 d R . . . .
C7 C 0.28559(10) 0.38201(16) 0.62903(14) 0.0124(3) Uani 1 1 d . . . . .
C8 C 0.27833(11) 0.3385(2) 0.76851(15) 0.0172(3) Uani 1 1 d . . . . .
H8A H 0.2820(14) 0.235(3) 0.780(2) 0.026 Uiso 1 1 d R . . . .
H8B H 0.2243(15) 0.371(2) 0.801(2) 0.026 Uiso 1 1 d R . . . .
H8C H 0.3275(15) 0.380(2) 0.823(2) 0.026 Uiso 1 1 d R . . . .
C9 C 0.50319(9) 0.35386(16) 0.62442(14) 0.0116(3) Uani 1 1 d . . . . .
C10 C 0.58498(9) 0.36401(16) 0.71234(13) 0.0115(3) Uani 1 1 d . . . . .
C11 C 0.59848(10) 0.48475(17) 0.79477(14) 0.0135(3) Uani 1 1 d . . . . .
H11 H 0.5560(13) 0.561(2) 0.7903(19) 0.016 Uiso 1 1 d R . . . .
C12 C 0.67278(10) 0.49354(17) 0.88130(14) 0.0140(3) Uani 1 1 d . . . . .
H12 H 0.6817(13) 0.577(2) 0.9367(19) 0.017 Uiso 1 1 d R . . . .
C13 C 0.73416(10) 0.37988(17) 0.88496(14) 0.0135(3) Uani 1 1 d . . . . .
C14 C 0.72352(10) 0.25998(17) 0.80348(14) 0.0138(3) Uani 1 1 d . . . . .
H14 H 0.7657(13) 0.183(2) 0.8067(19) 0.017 Uiso 1 1 d R . . . .
C15 C 0.64874(10) 0.25293(16) 0.71639(14) 0.0132(3) Uani 1 1 d . . . . .
H15 H 0.6396(13) 0.168(2) 0.6625(19) 0.016 Uiso 1 1 d R . . . .
C16 C 0.50576(11) 0.26917(18) 0.49981(15) 0.0156(3) Uani 1 1 d . . . . .
H16A H 0.5015(14) 0.164(2) 0.515(2) 0.023 Uiso 1 1 d R . . . .
H16B H 0.5613(14) 0.286(2) 0.461(2) 0.023 Uiso 1 1 d R . . . .
H16C H 0.4566(14) 0.297(2) 0.440(2) 0.023 Uiso 1 1 d 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
Cl1 C1 1.7419(15) . ?
Cl2 C13 1.7397(15) . ?
N1 N2 1.3961(17) . ?
N1 C7 1.2875(19) . ?
N2 C9 1.2885(19) . ?
C1 C2 1.384(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.95(2) . ?
C2 C3 1.388(2) . ?
C3 H3 0.95(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.399(2) . ?
C4 C7 1.481(2) . ?
C5 H5 0.95(2) . ?
C5 C6 1.388(2) . ?
C6 H6 0.94(2) . ?
C7 C8 1.502(2) . ?
C8 H8A 0.95(2) . ?
C8 H8B 0.95(2) . ?
C8 H8C 0.98(2) . ?
C9 C10 1.484(2) . ?
C9 C16 1.502(2) . ?
C10 C11 1.400(2) . ?
C10 C15 1.397(2) . ?
C11 H11 0.95(2) . ?
C11 C12 1.387(2) . ?
C12 H12 0.96(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.384(2) . ?
C14 H14 0.95(2) . ?
C14 C15 1.395(2) . ?
C15 H15 0.96(2) . ?
C16 H16A 0.98(2) . ?
C16 H16B 0.96(2) . ?
C16 H16C 0.97(2) . ?

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 N1 N2 115.17(12) . . ?
C9 N2 N1 115.17(12) . . ?
C2 C1 Cl1 119.46(12) . . ?
C2 C1 C6 121.73(14) . . ?
C6 C1 Cl1 118.81(13) . . ?
C1 C2 H2 119.7(13) . . ?
C1 C2 C3 118.99(15) . . ?
C3 C2 H2 121.3(13) . . ?
C2 C3 H3 120.0(13) . . ?
C2 C3 C4 120.74(15) . . ?
C4 C3 H3 119.3(13) . . ?
C3 C4 C7 120.94(14) . . ?
C5 C4 C3 118.91(14) . . ?
C5 C4 C7 120.15(13) . . ?
C4 C5 H5 119.6(12) . . ?
C6 C5 C4 120.87(14) . . ?
C6 C5 H5 119.5(12) . . ?
C1 C6 H6 119.5(13) . . ?
C5 C6 C1 118.73(15) . . ?
C5 C6 H6 121.8(13) . . ?
N1 C7 C4 116.16(13) . . ?
N1 C7 C8 124.72(13) . . ?
C4 C7 C8 119.12(13) . . ?
C7 C8 H8A 112.0(13) . . ?
C7 C8 H8B 112.2(13) . . ?
C7 C8 H8C 110.3(13) . . ?
H8A C8 H8B 107.9(19) . . ?
H8A C8 H8C 106.1(18) . . ?
H8B C8 H8C 108.1(18) . . ?
N2 C9 C10 115.58(13) . . ?
N2 C9 C16 125.23(13) . . ?
C10 C9 C16 119.17(13) . . ?
C11 C10 C9 120.12(13) . . ?
C15 C10 C9 120.99(13) . . ?
C15 C10 C11 118.88(13) . . ?
C10 C11 H11 118.7(12) . . ?
C12 C11 C10 121.00(14) . . ?
C12 C11 H11 120.3(12) . . ?
C11 C12 H12 120.4(12) . . ?
C11 C12 C13 118.80(14) . . ?
C13 C12 H12 120.8(12) . . ?
C12 C13 Cl2 119.01(12) . . ?
C14 C13 Cl2 119.30(12) . . ?
C14 C13 C12 121.69(14) . . ?
C13 C14 H14 121.1(12) . . ?
C13 C14 C15 118.92(14) . . ?
C15 C14 H14 119.9(12) . . ?
C10 C15 H15 119.9(12) . . ?
C14 C15 C10 120.70(14) . . ?
C14 C15 H15 119.3(12) . . ?
C9 C16 H16A 111.2(13) . . ?
C9 C16 H16B 110.0(13) . . ?
C9 C16 H16C 110.3(13) . . ?
H16A C16 H16B 107.1(18) . . ?
H16A C16 H16C 108.1(18) . . ?
H16B C16 H16C 110.1(17) . . ?

_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_s1_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc2f7mv5
_database_code_depnum_ccdc_archive 'CCDC 2241667'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        '4-bromoacetophenone azine'
_chemical_formula_moiety         'C16 H14 Br2 N2'
_chemical_formula_sum            'C16 H14 Br2 N2'
_chemical_formula_weight         394.11
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3239(7)
_cell_length_b                   10.3551(7)
_cell_length_c                   30.346(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2929.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      35.27
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.608
_shelx_estimated_absorpt_T_min   0.271
_exptl_absorpt_coefficient_mu    5.524
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.3416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            89495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.610
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker Photon II CMOS area detector'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IMuS microfocus Mo tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5045
_reflns_number_total             6144
_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       'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_data_collection       'Bruker Apex4 V.2022.1-1'
_computing_data_reduction        'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         6144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+2.2119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C14(H14), C15(H15), C2(H2), C6(H6), C5(H5), C12(H12)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.89224(2) 0.02138(2) 0.15806(2) 0.01721(4) Uani 1 1 d . . . . .
Br2 Br 0.92165(2) 0.74329(2) -0.26888(2) 0.01992(4) Uani 1 1 d . . . . .
N1 N 0.91929(13) 0.41318(12) -0.07567(4) 0.0141(2) Uani 1 1 d . . . . .
N2 N 0.91643(13) 0.32969(12) -0.03973(4) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.88894(15) 0.45251(13) -0.15135(4) 0.0120(2) Uani 1 1 d . . . . .
C3 C 0.99784(16) 0.54592(14) -0.15265(5) 0.0147(3) Uani 1 1 d . . . . .
H3 H 1.064699 0.551396 -0.129098 0.018 Uiso 1 1 calc R . . . .
C10 C 0.86579(15) 0.29253(13) 0.03513(4) 0.0121(2) Uani 1 1 d . . . . .
C7 C 0.87648(15) 0.36560(13) -0.11263(4) 0.0125(2) Uani 1 1 d . . . . .
C9 C 0.85824(15) 0.37572(13) -0.00459(4) 0.0117(2) Uani 1 1 d . . . . .
C11 C 0.98097(15) 0.20675(14) 0.04043(5) 0.0145(2) Uani 1 1 d . . . . .
H11 H 1.054406 0.203749 0.018754 0.017 Uiso 1 1 calc R . . . .
C16 C 0.78478(16) 0.50438(14) -0.00154(5) 0.0152(3) Uani 1 1 d . . . . .
H16A H 0.817302 0.559897 -0.025709 0.023 Uiso 1 1 calc GR . . . .
H16B H 0.808286 0.545047 0.026711 0.023 Uiso 1 1 calc GR . . . .
H16C H 0.680767 0.492187 -0.003631 0.023 Uiso 1 1 calc GR . . . .
C14 C 0.76581(15) 0.21576(14) 0.10410(4) 0.0138(2) Uani 1 1 d . . . . .
H14 H 0.692423 0.218067 0.125802 0.017 Uiso 1 1 calc R . . . .
C1 C 0.90831(16) 0.62276(14) -0.22179(4) 0.0139(3) Uani 1 1 d . . . . .
C15 C 0.75986(15) 0.29699(14) 0.06748(4) 0.0131(2) Uani 1 1 d . . . . .
H15 H 0.682566 0.356146 0.064562 0.016 Uiso 1 1 calc R . . . .
C13 C 0.88072(15) 0.13153(14) 0.10829(4) 0.0133(2) Uani 1 1 d . . . . .
C2 C 1.00889(16) 0.63045(14) -0.18801(5) 0.0158(3) Uani 1 1 d . . . . .
H2 H 1.083860 0.692494 -0.189117 0.019 Uiso 1 1 calc R . . . .
C8 C 0.81591(18) 0.23222(14) -0.11840(5) 0.0184(3) Uani 1 1 d . . . . .
H8A H 0.851698 0.175972 -0.094873 0.028 Uiso 1 1 calc GR . . . .
H8B H 0.845548 0.197645 -0.147055 0.028 Uiso 1 1 calc GR . . . .
H8C H 0.710985 0.236029 -0.117052 0.028 Uiso 1 1 calc GR . . . .
C6 C 0.80000(16) 0.53088(14) -0.22159(5) 0.0151(3) Uani 1 1 d . . . . .
H6 H 0.732485 0.526751 -0.244989 0.018 Uiso 1 1 calc R . . . .
C5 C 0.79220(15) 0.44470(14) -0.18635(4) 0.0137(2) Uani 1 1 d . . . . .
H5 H 0.720132 0.379850 -0.186165 0.016 Uiso 1 1 calc R . . . .
C12 C 0.98913(16) 0.12641(14) 0.07682(5) 0.0152(3) Uani 1 1 d . . . . .
H12 H 1.067534 0.068684 0.080252 0.018 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 C13 1.8958(14) . ?
Br2 C1 1.9013(14) . ?
N1 N2 1.3920(17) . ?
N1 C7 1.2882(18) . ?
N2 C9 1.2879(18) . ?
C4 C3 1.403(2) . ?
C4 C7 1.4847(19) . ?
C4 C5 1.3957(19) . ?
C3 C2 1.389(2) . ?
C10 C9 1.4831(19) . ?
C10 C11 1.403(2) . ?
C10 C15 1.393(2) . ?
C7 C8 1.502(2) . ?
C9 C16 1.5009(19) . ?
C11 C12 1.385(2) . ?
C14 C15 1.3947(19) . ?
C14 C13 1.387(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.387(2) . ?
C13 C12 1.392(2) . ?
C6 C5 1.395(2) . ?

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 N1 N2 116.01(12) . . ?
C9 N2 N1 115.28(12) . . ?
C3 C4 C7 119.79(12) . . ?
C5 C4 C3 119.10(13) . . ?
C5 C4 C7 121.10(13) . . ?
C2 C3 C4 120.67(13) . . ?
C11 C10 C9 119.82(12) . . ?
C15 C10 C9 121.32(12) . . ?
C15 C10 C11 118.86(13) . . ?
N1 C7 C4 115.65(12) . . ?
N1 C7 C8 124.72(13) . . ?
C4 C7 C8 119.62(12) . . ?
N2 C9 C10 115.97(12) . . ?
N2 C9 C16 124.88(13) . . ?
C10 C9 C16 119.15(12) . . ?
C12 C11 C10 120.93(13) . . ?
C13 C14 C15 118.87(13) . . ?
C2 C1 Br2 118.16(11) . . ?
C6 C1 Br2 120.07(11) . . ?
C6 C1 C2 121.76(13) . . ?
C10 C15 C14 120.88(13) . . ?
C14 C13 Br1 119.67(10) . . ?
C14 C13 C12 121.47(13) . . ?
C12 C13 Br1 118.86(11) . . ?
C3 C2 C1 118.89(13) . . ?
C1 C6 C5 118.70(13) . . ?
C6 C5 C4 120.84(13) . . ?
C11 C12 C13 118.97(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
