# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_3_6_dichlorocarbazole_7_7_8_8_tetracyanoquinodimethane
_database_code_depnum_ccdc_archive 'CCDC 2154402'
loop_
_audit_author_name
_audit_author_address
'Pan Shi'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-26
_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         'C6 H3.5 Cl N0.5, C6 H2 N2'
_chemical_formula_sum            'C12 H5.50 Cl N2.50'
_chemical_formula_weight         220.14
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.1500(2)
_cell_length_b                   13.1041(2)
_cell_length_c                   13.7735(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.503(2)
_cell_angle_gamma                90
_cell_volume                     2025.97(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8246
_cell_measurement_temperature    292.1(8)
_cell_measurement_theta_max      78.8860
_cell_measurement_theta_min      4.7950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       black
_exptl_crystal_F_000             896
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.194
_diffrn_reflns_theta_min         4.844
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.1(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  88.00   0.50    0.50    --    0.00  57.00 -30.00  232
  2  ω    -24.00  89.00   0.50    0.50    --    0.00  37.00  90.00  226
  3  ω    -45.00  -9.00   0.50    0.50    --    0.00 -57.00 120.00   72
  4  ω     -6.00  20.00   0.50    0.50    --    0.00 -82.00 -90.00   52
  5  ω    -85.00 -56.00   0.50    0.50    --    0.00 -57.00 120.00   58
  6  ω    124.00 172.00   0.50    2.50    --  106.20  45.00-150.00   96
  7  ω     85.00 122.00   0.50    2.50    --  106.20 -82.00 120.00   74
  8  ω     74.00 190.00   0.50    2.50    --  106.20  30.00 -60.00  232
  9  ω     73.00 196.00   0.50    2.50    --  106.20  30.00 -90.00  246
 10  ω     33.00 121.00   0.50    2.50    --  106.20 -82.00 -30.00  176
 11  ω     79.00 131.00   0.50    2.50    --  106.20 -61.00-150.00  104
 12  ω     20.00  83.00   0.50    2.50    --  106.20 -61.00   0.00  126
 13  ω     24.00  55.00   0.50    2.50    --  106.20 -82.00-180.00   62
 14  ω    107.00 133.00   0.50    2.50    --  106.20 -82.00-180.00   52
 15  ω     18.00  64.00   0.50    2.50    --  106.20 -82.00 120.00   92
 16  ω    131.00 193.00   0.50    2.50    --  106.20  30.00 150.00  124
 17  ω     20.00 123.00   0.50    2.50    --  106.20 -61.00  60.00  206
 18  ω     75.00 100.00   0.50    2.50    --  106.20  30.00 150.00   50
 19  ω     19.00 136.00   0.50    2.50    --  106.20 -82.00  60.00  234
 20  ω     18.00  49.00   0.50    2.50    --  106.20 -82.00-150.00   62
 21  ω     57.00 134.00   0.50    2.50    --  106.20 -82.00-150.00  154
 22  ω     26.00  51.00   0.50    2.50    --  106.20 -61.00-150.00   50
 23  ω     18.00  75.00   0.50    2.50    --  106.20 -77.00   0.00  114
 24  ω    108.00 134.00   0.50    2.50    --  106.20 -82.00-120.00   52
 25  ω     22.00 132.00   0.50    2.50    --  106.20 -61.00-180.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0898440000
_diffrn_orient_matrix_UB_12      -0.0879379000
_diffrn_orient_matrix_UB_13      -0.0420601000
_diffrn_orient_matrix_UB_21      -0.1028262000
_diffrn_orient_matrix_UB_22      0.0776154000
_diffrn_orient_matrix_UB_23      -0.0380273000
_diffrn_orient_matrix_UB_31      0.0126797000
_diffrn_orient_matrix_UB_32      0.0069331000
_diffrn_orient_matrix_UB_33      -0.1070579000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2070
_reflns_number_total             2169
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.155
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.065
_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)+(0.0732P)²+0.6005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C3(H3), C2(H2), C8(H8), C7(H7)
;
_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 0.62856(4) 0.11031(5) 0.60480(4) 0.0858(2) Uani 1 1 d . . . . .
N1 N 0.250000 0.41453(12) 0.500000 0.0539(4) Uani 1 2 d S T P . .
H1 H 0.249999 0.480159 0.499999 0.065 Uiso 1 2 calc RS T P . .
C6 C 0.39970(13) 0.17350(10) 0.54212(10) 0.0477(3) Uani 1 1 d . . . . .
H6 H 0.378149 0.104975 0.534783 0.057 Uiso 1 1 calc R . . . .
C4 C 0.34930(13) 0.35405(10) 0.52991(10) 0.0477(3) Uani 1 1 d . . . . .
C3 C 0.46888(16) 0.38149(12) 0.56578(12) 0.0599(4) Uani 1 1 d . . . . .
H3 H 0.491610 0.449735 0.573608 0.072 Uiso 1 1 calc R . . . .
C1 C 0.51733(14) 0.20269(13) 0.57648(11) 0.0572(4) Uani 1 1 d . . . . .
C2 C 0.55242(14) 0.30522(14) 0.58930(12) 0.0641(4) Uani 1 1 d . . . . .
H2 H 0.632931 0.321736 0.613928 0.077 Uiso 1 1 calc R . . . .
C5 C 0.31398(11) 0.25036(9) 0.51869(9) 0.0417(3) Uani 1 1 d . . . . .
N2 N 0.35954(13) 0.62065(11) 0.62854(13) 0.0686(4) Uani 1 1 d . . . . .
N3 N 0.40725(14) 0.95075(10) 0.66923(13) 0.0698(4) Uani 1 1 d . . . . .
C11 C 0.42347(12) 0.68873(11) 0.65324(11) 0.0503(3) Uani 1 1 d . . . . .
C12 C 0.44953(13) 0.87244(11) 0.67401(11) 0.0505(3) Uani 1 1 d . . . . .
C9 C 0.62497(11) 0.76200(9) 0.71644(9) 0.0403(3) Uani 1 1 d . . . . .
C8 C 0.67839(12) 0.66194(9) 0.72727(10) 0.0440(3) Uani 1 1 d . . . . .
H8 H 0.629893 0.604416 0.712142 0.053 Uiso 1 1 calc R . . . .
C10 C 0.50361(11) 0.77376(9) 0.68251(9) 0.0436(3) Uani 1 1 d . . . . .
C7 C 0.79667(12) 0.65060(9) 0.75875(10) 0.0439(3) Uani 1 1 d . . . . .
H7 H 0.828765 0.585370 0.764698 0.053 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
Cl1 C1 1.7438(16) . ?
N1 H1 0.8600 . ?
N1 C4 1.3685(17) 2_556 ?
N1 C4 1.3685(17) . ?
C6 H6 0.9300 . ?
C6 C1 1.377(2) . ?
C6 C5 1.3949(18) . ?
C4 C3 1.391(2) . ?
C4 C5 1.4155(17) . ?
C3 H3 0.9300 . ?
C3 C2 1.372(3) . ?
C1 C2 1.400(2) . ?
C2 H2 0.9300 . ?
C5 C5 1.439(3) 2_556 ?
N2 C11 1.1457(19) . ?
N3 C12 1.1382(19) . ?
C11 C10 1.4324(18) . ?
C12 C10 1.4348(18) . ?
C9 C8 1.4452(17) . ?
C9 C10 1.3743(18) . ?
C9 C7 1.4444(17) 7_666 ?
C8 H8 0.9300 . ?
C8 C7 1.3410(18) . ?
C7 H7 0.9300 . ?

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
C4 N1 H1 125.4 . . ?
C4 N1 H1 125.4 2_556 . ?
C4 N1 C4 109.22(15) 2_556 . ?
C1 C6 H6 121.2 . . ?
C1 C6 C5 117.64(13) . . ?
C5 C6 H6 121.2 . . ?
N1 C4 C3 129.63(13) . . ?
N1 C4 C5 109.12(13) . . ?
C3 C4 C5 121.24(14) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.25(14) . . ?
C2 C3 H3 120.9 . . ?
C6 C1 Cl1 119.86(12) . . ?
C6 C1 C2 122.41(14) . . ?
C2 C1 Cl1 117.74(12) . . ?
C3 C2 C1 120.48(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C6 C5 C4 119.97(13) . . ?
C6 C5 C5 133.77(8) . 2_556 ?
C4 C5 C5 106.26(8) . 2_556 ?
N2 C11 C10 179.07(16) . . ?
N3 C12 C10 178.74(16) . . ?
C10 C9 C8 121.19(11) . . ?
C10 C9 C7 121.05(11) . 7_666 ?
C7 C9 C8 117.75(11) 7_666 . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.15(11) . . ?
C7 C8 H8 119.4 . . ?
C11 C10 C12 115.93(12) . . ?
C9 C10 C11 122.26(12) . . ?
C9 C10 C12 121.81(11) . . ?
C9 C7 H7 119.5 7_666 . ?
C8 C7 C9 121.09(12) . 7_666 ?
C8 C7 H7 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 2.55 3.2246(19) 136.3 2_556

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
Cl1 C1 C2 C3 178.37(12) . . . . ?
N1 C4 C3 C2 -178.90(12) . . . . ?
N1 C4 C5 C6 178.51(10) . . . . ?
N1 C4 C5 C5 -0.87(15) . . . 2_556 ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C4 N1 C4 C3 179.89(17) 2_556 . . . ?
C4 N1 C4 C5 0.34(6) 2_556 . . . ?
C4 C3 C2 C1 0.5(2) . . . . ?
C3 C4 C5 C6 -1.08(19) . . . . ?
C3 C4 C5 C5 179.54(13) . . . 2_556 ?
C1 C6 C5 C4 0.42(18) . . . . ?
C1 C6 C5 C5 179.60(16) . . . 2_556 ?
C5 C6 C1 Cl1 -178.85(10) . . . . ?
C5 C6 C1 C2 0.7(2) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C9 C8 C7 C9 0.4(2) . . . 7_666 ?
C8 C9 C10 C11 -1.85(19) . . . . ?
C8 C9 C10 C12 178.33(12) . . . . ?
C10 C9 C8 C7 178.91(12) . . . . ?
C7 C9 C8 C7 -0.4(2) 7_666 . . . ?
C7 C9 C10 C11 177.38(11) 7_666 . . . ?
C7 C9 C10 C12 -2.43(19) 7_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.064
_oxdiff_exptl_absorpt_empirical_full_min 0.598
####################################################################### 
# 
# 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_3_6_dibromocarbazole_7_7_8_8_tetracyanoquinodimethane
_database_code_depnum_ccdc_archive 'CCDC 2154407'
loop_
_audit_author_name
_audit_author_address
'Pan Shi'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-26
_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         'C6 H3.5 Br1 N0.5, C6 H2 N2'
_chemical_formula_sum            'C12 H5.50 Br N2.50'
_chemical_formula_weight         264.60
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.3323(4)
_cell_length_b                   13.1469(3)
_cell_length_c                   13.9845(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.945(4)
_cell_angle_gamma                90
_cell_volume                     2072.19(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4446
_cell_measurement_temperature    293.74(10)
_cell_measurement_theta_max      78.5240
_cell_measurement_theta_min      4.0240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       black
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.102
_diffrn_reflns_theta_min         4.826
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.74(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  50.00   0.50    0.50    --    0.00  57.00 -30.00   74
  2  ω     28.00  87.00   0.50    0.50    --    0.00  57.00  60.00  118
  3  ω    -27.00  25.00   0.50    0.50    --    0.00  57.00  60.00  104
  4  ω    -28.00  -3.00   0.50    0.50    --    0.00  57.00 -30.00   50
  5  ω     62.00  89.00   0.50    1.00    --  106.20 -45.00  90.00   54
  6  ω     92.00 128.00   0.50    1.00    --  106.20  30.00  60.00   72
  7  ω     25.00 101.00   0.50    1.00    --  106.20 -45.00 -30.00  152
  8  ω     39.00  77.00   0.50    1.00    --  106.20 -45.00-150.00   76
  9  ω    137.00 163.00   0.50    1.00    --  106.20  30.00  60.00   52
 10  ω     19.00 129.00   0.50    1.00    --  106.20 -30.00-180.00  220
 11  ω    103.00 132.00   0.50    1.00    --  106.20 -45.00  90.00   58
 12  ω    101.00 140.00   0.50    1.00    --  106.20 -30.00 -60.00   78
 13  ω     78.00 173.00   0.50    1.00    --  106.20  61.00 120.00  190
 14  ω    108.00 162.00   0.50    1.00    --  106.20  30.00-120.00  108
 15  ω     77.00 134.00   0.50    1.00    --  106.20  61.00  90.00  114
 16  ω    150.00 194.00   0.50    1.00    --  106.20  61.00  90.00   88
 17  ω     25.00  50.00   0.50    1.00    --  106.20 -30.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1252268000
_diffrn_orient_matrix_UB_12      0.0434398000
_diffrn_orient_matrix_UB_13      -0.0616732000
_diffrn_orient_matrix_UB_21      0.0510048000
_diffrn_orient_matrix_UB_22      0.0760025000
_diffrn_orient_matrix_UB_23      -0.0547907000
_diffrn_orient_matrix_UB_31      -0.0200429000
_diffrn_orient_matrix_UB_32      -0.0779200000
_diffrn_orient_matrix_UB_33      -0.0878658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2029
_reflns_number_total             2197
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.341
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.135
_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)+(0.0532P)²+0.5514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: Br01(0.33333) Br1(0.33333) Br2(0.33333)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C8(H8), C7(H7), C5(H5), C6(H6)
;
_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
Br01 Br -0.1487(6) 0.1077(4) 0.3923(5) 0.0597(9) Uani 0.3333 1 d . . . A 3
N1 N 0.250000 0.42335(17) 0.500000 0.0529(5) Uani 1 2 d S T P . .
H1 H 0.250000 0.488769 0.499998 0.064 Uiso 1 2 calc RS T P . .
C9 C 0.62597(16) 0.76525(13) 0.71686(13) 0.0401(4) Uani 1 1 d . . . . .
N2 N 0.35816(19) 0.63088(15) 0.6247(2) 0.0657(5) Uani 1 1 d . . . . .
C2 C 0.10006(17) 0.18280(14) 0.45726(14) 0.0430(4) Uani 1 1 d . . . . .
H2 H 0.120984 0.114379 0.464413 0.052 Uiso 1 1 calc R . . . .
C10 C 0.50606(16) 0.78029(13) 0.68306(14) 0.0423(4) Uani 1 1 d . . . . .
N3 N 0.41686(19) 0.95943(15) 0.67323(18) 0.0665(5) Uani 1 1 d . . . . .
C3 C 0.18628(16) 0.25961(13) 0.48114(13) 0.0398(4) Uani 1 1 d . . . . .
C8 C 0.67526(16) 0.66441(13) 0.72526(14) 0.0442(4) Uani 1 1 d . . . . .
H8 H 0.624922 0.608392 0.708995 0.053 Uiso 1 1 calc R . . . .
C7 C 0.79243(17) 0.64991(13) 0.75612(15) 0.0442(4) Uani 1 1 d . . . . .
H7 H 0.821606 0.584088 0.760169 0.053 Uiso 1 1 calc R . . . .
C12 C 0.45600(18) 0.88018(15) 0.67661(17) 0.0485(4) Uani 1 1 d . . . . .
C4 C 0.1506(2) 0.36287(14) 0.46944(15) 0.0462(4) Uani 1 1 d . . . . .
C11 C 0.42312(16) 0.69735(15) 0.65139(16) 0.0488(4) Uani 1 1 d . . . . .
C1 C -0.01648(18) 0.21273(16) 0.42291(15) 0.0503(4) Uani 1 1 d . . . . .
C5 C 0.0318(2) 0.39074(15) 0.43246(19) 0.0561(5) Uani 1 1 d . . . . .
H5 H 0.009531 0.458840 0.423680 0.067 Uiso 1 1 calc R . . . .
C6 C -0.05168(19) 0.31495(18) 0.40921(17) 0.0566(5) Uani 1 1 d . . . . .
H6 H -0.131759 0.331529 0.384323 0.068 Uiso 1 1 calc R . . . .
Br1 Br -0.1233(6) 0.1128(6) 0.3963(7) 0.0596(9) Uani 0.3333 1 d . . . A 1
Br2 Br -0.1427(7) 0.1211(6) 0.3915(4) 0.0718(15) Uani 0.3333 1 d . . . A 2


_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
Br01 C1 2.045(6) . ?
N1 H1 0.8600 . ?
N1 C4 1.376(3) . ?
N1 C4 1.376(3) 2_556 ?
C9 C10 1.372(3) . ?
C9 C8 1.443(2) . ?
C9 C7 1.446(2) 7_666 ?
N2 C11 1.141(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(3) . ?
C2 C1 1.375(3) . ?
C10 C12 1.438(3) . ?
C10 C11 1.437(3) . ?
N3 C12 1.141(3) . ?
C3 C3 1.441(4) 2_556 ?
C3 C4 1.416(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.343(3) . ?
C7 H7 0.9300 . ?
C4 C5 1.389(3) . ?
C1 C6 1.401(3) . ?
C1 Br1 1.789(7) . ?
C1 Br2 1.874(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?

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
C4 N1 H1 125.3 2_556 . ?
C4 N1 H1 125.3 . . ?
C4 N1 C4 109.4(2) . 2_556 ?
C10 C9 C8 121.33(16) . . ?
C10 C9 C7 121.16(16) . 7_666 ?
C8 C9 C7 117.51(16) . 7_666 ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.41(17) . . ?
C9 C10 C12 121.90(16) . . ?
C9 C10 C11 122.00(17) . . ?
C11 C10 C12 116.10(17) . . ?
C2 C3 C3 134.03(10) . 2_556 ?
C2 C3 C4 119.45(17) . . ?
C4 C3 C3 106.51(12) . 2_556 ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.28(16) . . ?
C7 C8 H8 119.4 . . ?
C9 C7 H7 119.4 7_666 . ?
C8 C7 C9 121.21(17) . 7_666 ?
C8 C7 H7 119.4 . . ?
N3 C12 C10 178.9(2) . . ?
N1 C4 C3 108.78(18) . . ?
N1 C4 C5 129.41(18) . . ?
C5 C4 C3 121.82(19) . . ?
N2 C11 C10 178.5(2) . . ?
C2 C1 Br01 120.8(3) . . ?
C2 C1 C6 122.96(19) . . ?
C2 C1 Br1 116.1(3) . . ?
C2 C1 Br2 123.3(3) . . ?
C6 C1 Br01 116.3(3) . . ?
C6 C1 Br1 121.0(3) . . ?
C6 C1 Br2 113.7(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.19(18) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 2.53 3.221(3) 137.5 2_556

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
Br01 C1 C6 C5 177.1(2) . . . . ?
N1 C4 C5 C6 -178.48(18) . . . . ?
C9 C8 C7 C9 0.6(3) . . . 7_666 ?
C2 C3 C4 N1 178.38(14) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C10 C9 C8 C7 178.49(18) . . . . ?
C3 C2 C1 Br01 -177.2(2) . . . . ?
C3 C2 C1 C6 1.3(3) . . . . ?
C3 C2 C1 Br1 -178.6(3) . . . . ?
C3 C2 C1 Br2 -178.0(3) . . . . ?
C3 C3 C4 N1 -1.1(2) 2_556 . . . ?
C3 C3 C4 C5 179.0(2) 2_556 . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C8 C9 C10 C12 178.54(18) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C7 C9 C10 C12 -2.4(3) 7_666 . . . ?
C7 C9 C10 C11 177.16(17) 7_666 . . . ?
C7 C9 C8 C7 -0.6(3) 7_666 . . . ?
C4 N1 C4 C3 0.43(9) 2_556 . . . ?
C4 N1 C4 C5 -179.6(3) 2_556 . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C1 C2 C3 C3 179.5(2) . . . 2_556 ?
C1 C2 C3 C4 0.2(3) . . . . ?
Br1 C1 C6 C5 178.4(4) . . . . ?
Br2 C1 C6 C5 178.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.681
_oxdiff_exptl_absorpt_empirical_full_min 0.648
