# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_SPA722
_database_code_depnum_ccdc_archive 'CCDC 2259618'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-01-08 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3,6-dichloro-9H-carbazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Cl2 N'
_chemical_formula_sum            'C12 H7 Cl2 N'
_chemical_formula_weight         236.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1166 0.1176 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9260(12)
_cell_length_b                   22.325(5)
_cell_length_c                   22.507(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2977.6(10)
_cell_formula_units_Z            12
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    105897
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.395
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30604
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.103
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8263
_reflns_number_gt                7845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²+0.1663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.051(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         8263
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.04169(12) 0.66804(3) 0.89828(2) 0.03447(15) Uani 1 1 d . . . . .
Cl2 Cl -0.07829(13) 0.70124(3) 0.52130(2) 0.04095(17) Uani 1 1 d . . . . .
N1 N 0.5438(4) 0.60487(9) 0.69919(9) 0.0299(4) Uani 1 1 d . . . . .
H1N1 H 0.676907 0.588575 0.696924 0.036 Uiso 1 1 calc R U . . .
C1 C 0.4282(4) 0.61624(10) 0.75091(10) 0.0256(4) Uani 1 1 d . . . . .
C2 C 0.4932(4) 0.60584(11) 0.80944(10) 0.0299(5) Uani 1 1 d . . . . .
H2 H 0.632625 0.587862 0.818290 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3469(5) 0.62271(11) 0.85404(10) 0.0308(5) Uani 1 1 d . . . . .
H3 H 0.387353 0.616647 0.893968 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1381(4) 0.64884(10) 0.84027(9) 0.0255(4) Uani 1 1 d . . . . .
C5 C 0.0696(4) 0.65952(9) 0.78217(9) 0.0241(4) Uani 1 1 d . . . . .
H5 H -0.070648 0.677265 0.773763 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2177(4) 0.64283(9) 0.73673(9) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.2104(4) 0.64750(10) 0.67249(9) 0.0228(4) Uani 1 1 d . . . . .
C8 C 0.0536(4) 0.67154(10) 0.63258(9) 0.0251(4) Uani 1 1 d . . . . .
H8 H -0.084500 0.687387 0.645783 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1100(5) 0.67109(11) 0.57276(9) 0.0288(5) Uani 1 1 d . . . . .
C10 C 0.3128(5) 0.64731(12) 0.55189(11) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.344601 0.648038 0.510974 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4671(5) 0.62273(11) 0.59080(10) 0.0316(5) Uani 1 1 d . . . . .
H11 H 0.603059 0.606048 0.577041 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4149(4) 0.62345(10) 0.65116(10) 0.0265(4) Uani 1 1 d . . . . .
Cl3 Cl 1.07133(11) 0.49693(3) 0.80603(2) 0.03389(15) Uani 1 1 d . . . . .
Cl4 Cl 1.08026(14) 0.54671(4) 0.43045(3) 0.04670(19) Uani 1 1 d . . . . .
N2 N 0.4674(4) 0.44461(10) 0.60747(9) 0.0324(4) Uani 1 1 d . . . . .
H2N2 H 0.334143 0.428435 0.605243 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5893(4) 0.45333(10) 0.65909(10) 0.0270(4) Uani 1 1 d . . . . .
C14 C 0.5287(4) 0.44018(10) 0.71753(11) 0.0299(5) Uani 1 1 d . . . . .
H14 H 0.389316 0.422145 0.726380 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6799(4) 0.45451(11) 0.76195(11) 0.0301(5) Uani 1 1 d . . . . .
H15 H 0.643588 0.446167 0.801754 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8863(4) 0.48130(10) 0.74823(10) 0.0254(4) Uani 1 1 d . . . . .
C17 C 0.9492(4) 0.49525(9) 0.69031(9) 0.0237(4) Uani 1 1 d . . . . .
H17 H 1.088440 0.513528 0.681906 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7964(4) 0.48093(9) 0.64512(10) 0.0237(4) Uani 1 1 d . . . . .
C19 C 0.7983(4) 0.48931(10) 0.58098(10) 0.0246(4) Uani 1 1 d . . . . .
C20 C 0.9527(4) 0.51464(10) 0.54154(10) 0.0279(4) Uani 1 1 d . . . . .
H20 H 1.090103 0.530800 0.554923 0.033 Uiso 1 1 calc R U . . .
C21 C 0.8954(5) 0.51506(12) 0.48174(10) 0.0342(5) Uani 1 1 d . . . . .
C22 C 0.6906(5) 0.49128(14) 0.46112(12) 0.0399(6) Uani 1 1 d . . . . .
H22 H 0.657192 0.492572 0.420309 0.048 Uiso 1 1 calc R U . . .
C23 C 0.5380(5) 0.46612(13) 0.49982(11) 0.0374(6) Uani 1 1 d . . . . .
H23 H 0.401665 0.449686 0.486049 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5918(4) 0.46576(11) 0.55996(11) 0.0297(5) Uani 1 1 d . . . . .
Cl5 Cl 1.05400(13) 0.84903(3) 0.98464(2) 0.03598(16) Uani 1 1 d . . . . .
Cl6 Cl 1.08764(12) 0.85280(3) 0.60658(2) 0.03867(16) Uani 1 1 d . . . . .
N3 N 0.4666(4) 0.76988(9) 0.79115(8) 0.0299(4) Uani 1 1 d . . . . .
H3N3 H 0.333162 0.753671 0.790302 0.036 Uiso 1 1 calc R U . . .
C25 C 0.5851(4) 0.78475(10) 0.84175(10) 0.0267(4) Uani 1 1 d . . . . .
C26 C 0.5219(4) 0.77828(11) 0.90135(10) 0.0301(5) Uani 1 1 d . . . . .
H26 H 0.382866 0.760929 0.911771 0.036 Uiso 1 1 calc R U . . .
C27 C 0.6698(5) 0.79814(11) 0.94415(10) 0.0303(5) Uani 1 1 d . . . . .
H27 H 0.631953 0.794197 0.984517 0.036 Uiso 1 1 calc R U . . .
C28 C 0.8754(4) 0.82409(10) 0.92827(9) 0.0262(4) Uani 1 1 d . . . . .
C29 C 0.9419(4) 0.83097(10) 0.86949(9) 0.0239(4) Uani 1 1 d . . . . .
H29 H 1.080694 0.848781 0.859624 0.029 Uiso 1 1 calc R U . . .
C30 C 0.7940(4) 0.81029(10) 0.82551(9) 0.0225(4) Uani 1 1 d . . . . .
C31 C 0.8007(4) 0.81016(10) 0.76120(9) 0.0225(4) Uani 1 1 d . . . . .
C32 C 0.9569(4) 0.83082(10) 0.71947(9) 0.0245(4) Uani 1 1 d . . . . .
H32 H 1.096026 0.847091 0.731380 0.029 Uiso 1 1 calc R U . . .
C33 C 0.8998(4) 0.82649(10) 0.65995(9) 0.0268(4) Uani 1 1 d . . . . .
C34 C 0.6947(4) 0.80195(11) 0.64108(10) 0.0300(5) Uani 1 1 d . . . . .
H34 H 0.661256 0.800255 0.600284 0.036 Uiso 1 1 calc R U . . .
C35 C 0.5410(4) 0.78023(10) 0.68179(10) 0.0294(5) Uani 1 1 d . . . . .
H35 H 0.404473 0.762821 0.669364 0.035 Uiso 1 1 calc R U . . .
C36 C 0.5946(4) 0.78491(10) 0.74191(10) 0.0249(4) 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 C4 1.739(2) . ?
Cl2 C9 1.744(3) . ?
N1 C1 1.374(3) . ?
N1 C12 1.387(3) . ?
N1 H1N1 0.8700 . ?
C1 C2 1.392(3) . ?
C1 C6 1.418(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.403(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(3) . ?
C5 C6 1.398(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.450(3) . ?
C7 C8 1.399(3) . ?
C7 C12 1.410(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.395(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9400 . ?
Cl3 C16 1.737(2) . ?
Cl4 C21 1.741(3) . ?
N2 C13 1.382(3) . ?
N2 C24 1.382(3) . ?
N2 H2N2 0.8700 . ?
C13 C14 1.395(3) . ?
C13 C18 1.409(3) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.391(3) . ?
C17 C18 1.399(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.456(3) . ?
C19 C20 1.395(3) . ?
C19 C24 1.413(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.404(4) . ?
C22 C23 1.375(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.391(3) . ?
C23 H23 0.9400 . ?
Cl5 C28 1.743(2) . ?
Cl6 C33 1.740(2) . ?
N3 C25 1.379(3) . ?
N3 C36 1.384(3) . ?
N3 H3N3 0.8700 . ?
C25 C26 1.400(3) . ?
C25 C30 1.411(3) . ?
C26 C27 1.376(4) . ?
C26 H26 0.9400 . ?
C27 C28 1.396(4) . ?
C27 H27 0.9400 . ?
C28 C29 1.389(3) . ?
C29 C30 1.401(3) . ?
C29 H29 0.9400 . ?
C30 C31 1.448(3) . ?
C31 C32 1.397(3) . ?
C31 C36 1.414(3) . ?
C32 C33 1.385(3) . ?
C32 H32 0.9400 . ?
C33 C34 1.399(4) . ?
C34 C35 1.380(4) . ?
C34 H34 0.9400 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 109.3(2) . . ?
C1 N1 H1N1 125.4 . . ?
C12 N1 H1N1 125.4 . . ?
N1 C1 C2 129.3(2) . . ?
N1 C1 C6 108.98(19) . . ?
C2 C1 C6 121.8(2) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 Cl1 119.04(19) . . ?
C3 C4 Cl1 118.49(17) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 133.7(2) . . ?
C1 C6 C7 106.31(19) . . ?
C8 C7 C12 119.9(2) . . ?
C8 C7 C6 133.4(2) . . ?
C12 C7 C6 106.6(2) . . ?
C9 C8 C7 117.4(2) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C8 C9 C10 122.5(2) . . ?
C8 C9 Cl2 119.2(2) . . ?
C10 C9 Cl2 118.32(17) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 117.8(2) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
N1 C12 C11 129.3(2) . . ?
N1 C12 C7 108.78(19) . . ?
C11 C12 C7 121.8(2) . . ?
C13 N2 C24 108.9(2) . . ?
C13 N2 H2N2 125.6 . . ?
C24 N2 H2N2 125.6 . . ?
N2 C13 C14 129.0(2) . . ?
N2 C13 C18 109.2(2) . . ?
C14 C13 C18 121.8(2) . . ?
C15 C14 C13 117.9(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 122.5(2) . . ?
C17 C16 Cl3 119.19(18) . . ?
C15 C16 Cl3 118.27(17) . . ?
C16 C17 C18 117.2(2) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 C19 133.4(2) . . ?
C13 C18 C19 106.5(2) . . ?
C20 C19 C24 120.4(2) . . ?
C20 C19 C18 133.5(2) . . ?
C24 C19 C18 106.1(2) . . ?
C21 C20 C19 117.3(2) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C20 C21 C22 122.0(3) . . ?
C20 C21 Cl4 119.5(2) . . ?
C22 C21 Cl4 118.58(19) . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 117.9(2) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
N2 C24 C23 129.3(2) . . ?
N2 C24 C19 109.3(2) . . ?
C23 C24 C19 121.5(2) . . ?
C25 N3 C36 108.9(2) . . ?
C25 N3 H3N3 125.5 . . ?
C36 N3 H3N3 125.5 . . ?
N3 C25 C26 129.1(2) . . ?
N3 C25 C30 109.3(2) . . ?
C26 C25 C30 121.7(2) . . ?
C27 C26 C25 117.8(2) . . ?
C27 C26 H26 121.1 . . ?
C25 C26 H26 121.1 . . ?
C26 C27 C28 120.7(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C28 C27 122.5(2) . . ?
C29 C28 Cl5 119.06(19) . . ?
C27 C28 Cl5 118.43(17) . . ?
C28 C29 C30 117.3(2) . . ?
C28 C29 H29 121.3 . . ?
C30 C29 H29 121.3 . . ?
C29 C30 C25 119.95(19) . . ?
C29 C30 C31 133.6(2) . . ?
C25 C30 C31 106.4(2) . . ?
C32 C31 C36 119.9(2) . . ?
C32 C31 C30 133.6(2) . . ?
C36 C31 C30 106.5(2) . . ?
C33 C32 C31 117.7(2) . . ?
C33 C32 H32 121.1 . . ?
C31 C32 H32 121.1 . . ?
C32 C33 C34 122.2(2) . . ?
C32 C33 Cl6 119.2(2) . . ?
C34 C33 Cl6 118.58(17) . . ?
C35 C34 C33 120.6(2) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 117.9(2) . . ?
C34 C35 H35 121.0 . . ?
C36 C35 H35 121.1 . . ?
N3 C36 C35 129.4(2) . . ?
N3 C36 C31 108.92(19) . . ?
C35 C36 C31 121.7(2) . . ?

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
C12 N1 C1 C2 -179.1(2) . . . . ?
C12 N1 C1 C6 0.2(3) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 Cl1 178.9(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
Cl1 C4 C5 C6 -179.27(17) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
N1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1 C1 C6 C7 -0.2(2) . . . . ?
C2 C1 C6 C7 179.0(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C1 C6 C7 C8 -177.1(2) . . . . ?
C5 C6 C7 C12 178.8(2) . . . . ?
C1 C6 C7 C12 0.3(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C7 C8 C9 Cl2 -179.33(17) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
Cl2 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C1 N1 C12 C11 177.5(2) . . . . ?
C1 N1 C12 C7 0.0(3) . . . . ?
C10 C11 C12 N1 -176.2(2) . . . . ?
C10 C11 C12 C7 0.9(4) . . . . ?
C8 C7 C12 N1 177.6(2) . . . . ?
C6 C7 C12 N1 -0.2(2) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C6 C7 C12 C11 -177.8(2) . . . . ?
C24 N2 C13 C14 178.4(2) . . . . ?
C24 N2 C13 C18 0.3(3) . . . . ?
N2 C13 C14 C15 -178.6(2) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C14 C15 C16 Cl3 -178.81(19) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
Cl3 C16 C17 C18 178.94(16) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C16 C17 C18 C19 178.5(2) . . . . ?
N2 C13 C18 C17 179.1(2) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
N2 C13 C18 C19 0.1(2) . . . . ?
C14 C13 C18 C19 -178.2(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C13 C18 C19 C20 178.8(2) . . . . ?
C17 C18 C19 C24 -179.3(2) . . . . ?
C13 C18 C19 C24 -0.4(2) . . . . ?
C24 C19 C20 C21 -0.6(3) . . . . ?
C18 C19 C20 C21 -179.6(2) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C19 C20 C21 Cl4 179.41(18) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
Cl4 C21 C22 C23 -179.6(2) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C13 N2 C24 C23 179.6(3) . . . . ?
C13 N2 C24 C19 -0.6(3) . . . . ?
C22 C23 C24 N2 178.6(3) . . . . ?
C22 C23 C24 C19 -1.2(4) . . . . ?
C20 C19 C24 N2 -178.7(2) . . . . ?
C18 C19 C24 N2 0.6(3) . . . . ?
C20 C19 C24 C23 1.1(4) . . . . ?
C18 C19 C24 C23 -179.6(2) . . . . ?
C36 N3 C25 C26 179.3(2) . . . . ?
C36 N3 C25 C30 0.3(3) . . . . ?
N3 C25 C26 C27 -178.4(2) . . . . ?
C30 C25 C26 C27 0.5(3) . . . . ?
C25 C26 C27 C28 0.3(4) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C26 C27 C28 Cl5 179.35(19) . . . . ?
C27 C28 C29 C30 -0.4(3) . . . . ?
Cl5 C28 C29 C30 179.92(17) . . . . ?
C28 C29 C30 C25 1.2(3) . . . . ?
C28 C29 C30 C31 178.9(2) . . . . ?
N3 C25 C30 C29 177.9(2) . . . . ?
C26 C25 C30 C29 -1.2(3) . . . . ?
N3 C25 C30 C31 -0.4(3) . . . . ?
C26 C25 C30 C31 -179.6(2) . . . . ?
C29 C30 C31 C32 -0.3(5) . . . . ?
C25 C30 C31 C32 177.7(2) . . . . ?
C29 C30 C31 C36 -177.6(2) . . . . ?
C25 C30 C31 C36 0.4(2) . . . . ?
C36 C31 C32 C33 1.2(3) . . . . ?
C30 C31 C32 C33 -175.9(2) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C31 C32 C33 Cl6 178.97(17) . . . . ?
C32 C33 C34 C35 -0.8(4) . . . . ?
Cl6 C33 C34 C35 179.65(19) . . . . ?
C33 C34 C35 C36 1.5(3) . . . . ?
C25 N3 C36 C35 -177.4(2) . . . . ?
C25 N3 C36 C31 0.0(3) . . . . ?
C34 C35 C36 N3 176.1(2) . . . . ?
C34 C35 C36 C31 -1.0(3) . . . . ?
C32 C31 C36 N3 -178.0(2) . . . . ?
C30 C31 C36 N3 -0.2(3) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
C30 C31 C36 C35 177.4(2) . . . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_SPA870
_database_code_depnum_ccdc_archive 'CCDC 2259620'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-01-08 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        3,6-diiodo-9H-carbazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 I2 N'
_chemical_formula_sum            'C12 H7 I2 N'
_chemical_formula_weight         418.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.6366 1.4692 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.1760(8)
_cell_length_b                   11.111(2)
_cell_length_c                   12.236(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.14(3)
_cell_angle_gamma                90
_cell_volume                     566.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    27756
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.455
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    3.931
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5095
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_av_R_equivalents  0.1215
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2792
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.937

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.47028(15) 0.55220(5) 0.22384(4) 0.0324(2) Uani 1 1 d . . . . .
I2 I 0.52170(16) 0.70886(6) 0.94652(4) 0.0351(2) Uani 1 1 d . . . . .
N1 N 0.004(2) 0.2996(9) 0.6400(7) 0.0325(18) Uani 1 1 d . . . . .
H1 H -0.101527 0.233460 0.650889 0.039 Uiso 1 1 calc R U . . .
C1 C 0.104(2) 0.3807(8) 0.7204(7) 0.0277(17) Uani 1 1 d . . . . .
C2 C 0.055(2) 0.3768(8) 0.8326(8) 0.0290(18) Uani 1 1 d . . . . .
H2 H -0.056565 0.313313 0.864159 0.035 Uiso 1 1 calc R U . . .
C3 C 0.182(2) 0.4735(11) 0.8955(8) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.155402 0.474890 0.971338 0.038 Uiso 1 1 calc R U . . .
C4 C 0.346(2) 0.5674(9) 0.8475(7) 0.0247(15) Uani 1 1 d . . . . .
C5 C 0.396(2) 0.5697(9) 0.7363(7) 0.0293(18) Uani 1 1 d . . . . .
H5 H 0.508752 0.633381 0.705507 0.035 Uiso 1 1 calc R U . . .
C6 C 0.276(2) 0.4759(8) 0.6720(8) 0.0260(17) Uani 1 1 d . . . . .
C7 C 0.268(2) 0.4500(8) 0.5550(8) 0.0260(17) Uani 1 1 d . . . . .
C8 C 0.387(2) 0.5109(9) 0.4661(7) 0.0273(16) Uani 1 1 d . . . . .
H8 H 0.505967 0.582293 0.475584 0.033 Uiso 1 1 calc R U . . .
C9 C 0.321(3) 0.4613(9) 0.3620(8) 0.0281(18) Uani 1 1 d . . . . .
C10 C 0.156(2) 0.3544(9) 0.3463(7) 0.0291(18) Uani 1 1 d . . . . .
H10 H 0.119140 0.323963 0.275029 0.035 Uiso 1 1 calc R U . . .
C11 C 0.043(3) 0.2899(9) 0.4368(8) 0.031(2) Uani 1 1 d . . . . .
H11 H -0.064957 0.216126 0.426720 0.037 Uiso 1 1 calc R U . . .
C12 C 0.096(3) 0.3395(9) 0.5408(8) 0.0299(19) 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
I1 C9 2.094(10) . ?
I2 C4 2.094(9) . ?
N1 C12 1.367(14) . ?
N1 C1 1.382(13) . ?
N1 H1 0.8700 . ?
C1 C2 1.400(14) . ?
C1 C6 1.424(12) . ?
C2 C3 1.408(14) . ?
C2 H2 0.9400 . ?
C3 C4 1.395(15) . ?
C3 H3 0.9400 . ?
C4 C5 1.388(12) . ?
C5 C6 1.384(13) . ?
C5 H5 0.9400 . ?
C6 C7 1.459(13) . ?
C7 C8 1.395(13) . ?
C7 C12 1.430(14) . ?
C8 C9 1.401(12) . ?
C8 H8 0.9400 . ?
C9 C10 1.380(14) . ?
C10 C11 1.422(14) . ?
C10 H10 0.9400 . ?
C11 C12 1.393(13) . ?
C11 H11 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C1 109.3(9) . . ?
C12 N1 H1 125.3 . . ?
C1 N1 H1 125.3 . . ?
N1 C1 C2 128.5(9) . . ?
N1 C1 C6 109.2(8) . . ?
C2 C1 C6 122.3(9) . . ?
C1 C2 C3 116.2(9) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C4 C3 C2 121.2(9) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 122.1(9) . . ?
C5 C4 I2 119.1(7) . . ?
C3 C4 I2 118.8(6) . . ?
C6 C5 C4 118.2(9) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 119.9(9) . . ?
C5 C6 C7 133.9(8) . . ?
C1 C6 C7 106.1(8) . . ?
C8 C7 C12 121.3(9) . . ?
C8 C7 C6 132.9(9) . . ?
C12 C7 C6 105.8(8) . . ?
C7 C8 C9 117.2(9) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 122.5(9) . . ?
C10 C9 I1 118.0(7) . . ?
C8 C9 I1 119.4(7) . . ?
C9 C10 C11 120.6(9) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.0(10) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N1 C12 C11 130.2(10) . . ?
N1 C12 C7 109.6(9) . . ?
C11 C12 C7 120.3(10) . . ?

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
C12 N1 C1 C2 178.3(10) . . . . ?
C12 N1 C1 C6 -1.5(12) . . . . ?
N1 C1 C2 C3 -179.1(9) . . . . ?
C6 C1 C2 C3 0.6(14) . . . . ?
C1 C2 C3 C4 0.2(14) . . . . ?
C2 C3 C4 C5 -0.9(14) . . . . ?
C2 C3 C4 I2 179.2(8) . . . . ?
C3 C4 C5 C6 0.6(14) . . . . ?
I2 C4 C5 C6 -179.5(7) . . . . ?
C4 C5 C6 C1 0.3(14) . . . . ?
C4 C5 C6 C7 177.0(10) . . . . ?
N1 C1 C6 C5 178.9(9) . . . . ?
C2 C1 C6 C5 -0.9(14) . . . . ?
N1 C1 C6 C7 1.4(10) . . . . ?
C2 C1 C6 C7 -178.4(9) . . . . ?
C5 C6 C7 C8 1.3(18) . . . . ?
C1 C6 C7 C8 178.3(11) . . . . ?
C5 C6 C7 C12 -177.8(10) . . . . ?
C1 C6 C7 C12 -0.8(10) . . . . ?
C12 C7 C8 C9 2.0(14) . . . . ?
C6 C7 C8 C9 -177.0(10) . . . . ?
C7 C8 C9 C10 -2.4(15) . . . . ?
C7 C8 C9 I1 176.9(7) . . . . ?
C8 C9 C10 C11 0.6(15) . . . . ?
I1 C9 C10 C11 -178.6(8) . . . . ?
C9 C10 C11 C12 1.5(15) . . . . ?
C1 N1 C12 C11 -178.4(10) . . . . ?
C1 N1 C12 C7 1.0(12) . . . . ?
C10 C11 C12 N1 177.4(10) . . . . ?
C10 C11 C12 C7 -1.9(15) . . . . ?
C8 C7 C12 N1 -179.3(9) . . . . ?
C6 C7 C12 N1 -0.1(11) . . . . ?
C8 C7 C12 C11 0.1(14) . . . . ?
C6 C7 C12 C11 179.3(9) . . . . ?

_refine_diff_density_max         2.215
_refine_diff_density_min         -1.752
_refine_diff_density_rms         0.391

####################################################################### 
# 
# 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_SPA721
_database_code_depnum_ccdc_archive 'CCDC 2259619'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2024-01-08 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3,6-dibromo-9H-carbazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H7 Br2 N'
_chemical_formula_sum            'C12 H7 Br2 N'
_chemical_formula_weight         325.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.0842 1.9122 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0100(12)
_cell_length_b                   23.086(5)
_cell_length_c                   15.133(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.80(3)
_cell_angle_gamma                90
_cell_volume                     2099.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    73199
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    5.145
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20920
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.381
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             5545
_reflns_number_gt                4958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1167P)²+5.0958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5545
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.32980(8) 0.84700(2) 0.75216(3) 0.03173(15) Uani 1 1 d . . . . .
Br2 Br 1.33248(9) 0.47010(2) 0.68919(4) 0.04059(16) Uani 1 1 d . . . . .
N1 N 0.7231(7) 0.64952(18) 0.8401(3) 0.0311(8) Uani 1 1 d . . . . .
H1N1 H 0.591979 0.647630 0.863585 0.037 Uiso 1 1 calc R U . . .
C1 C 0.8434(7) 0.6998(2) 0.8264(3) 0.0269(8) Uani 1 1 d . . . . .
C2 C 0.7855(8) 0.7573(2) 0.8441(3) 0.0297(8) Uani 1 1 d . . . . .
H2 H 0.649380 0.766400 0.870640 0.036 Uiso 1 1 calc R U . . .
C3 C 0.9328(8) 0.8002(2) 0.8215(3) 0.0285(8) Uani 1 1 d . . . . .
H3 H 0.898393 0.839161 0.832876 0.034 Uiso 1 1 calc R U . . .
C4 C 1.1349(7) 0.78579(19) 0.7814(3) 0.0254(8) Uani 1 1 d . . . . .
C5 C 1.1959(7) 0.72900(18) 0.7622(3) 0.0236(7) Uani 1 1 d . . . . .
H5 H 1.331854 0.720504 0.735088 0.028 Uiso 1 1 calc R U . . .
C6 C 1.0466(7) 0.68507(18) 0.7850(3) 0.0232(7) Uani 1 1 d . . . . .
C7 C 1.0458(7) 0.62244(18) 0.7752(3) 0.0247(7) Uani 1 1 d . . . . .
C8 C 1.1966(7) 0.5839(2) 0.7382(3) 0.0269(8) Uani 1 1 d . . . . .
H8 H 1.331198 0.596564 0.713907 0.032 Uiso 1 1 calc R U . . .
C9 C 1.1371(8) 0.5254(2) 0.7392(3) 0.0311(9) Uani 1 1 d . . . . .
C10 C 0.9377(9) 0.5057(2) 0.7745(4) 0.0360(10) Uani 1 1 d . . . . .
H10 H 0.904721 0.465931 0.773502 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7876(9) 0.5442(2) 0.8112(4) 0.0344(10) Uani 1 1 d . . . . .
H11 H 0.653222 0.531341 0.835429 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8446(8) 0.6030(2) 0.8106(3) 0.0282(8) Uani 1 1 d . . . . .
Br3 Br 0.21240(9) 0.94254(2) 0.48614(3) 0.03493(15) Uani 1 1 d . . . . .
Br4 Br 0.16220(9) 0.56421(2) 0.46618(4) 0.03636(15) Uani 1 1 d . . . . .
N2 N 0.8022(7) 0.74502(18) 0.5981(3) 0.0315(8) Uani 1 1 d . . . . .
H2N2 H 0.934133 0.743215 0.622363 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6894(7) 0.79560(19) 0.5770(3) 0.0255(8) Uani 1 1 d . . . . .
C14 C 0.7546(8) 0.8528(2) 0.5893(3) 0.0312(9) Uani 1 1 d . . . . .
H14 H 0.892748 0.861992 0.615601 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6094(8) 0.8959(2) 0.5615(3) 0.0306(9) Uani 1 1 d . . . . .
H15 H 0.648033 0.935070 0.569395 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4050(8) 0.88138(18) 0.5218(3) 0.0269(8) Uani 1 1 d . . . . .
C17 C 0.3354(7) 0.82472(18) 0.5093(3) 0.0247(7) Uani 1 1 d . . . . .
H17 H 0.196963 0.816047 0.482882 0.030 Uiso 1 1 calc R U . . .
C18 C 0.4812(7) 0.78085(18) 0.5380(3) 0.0233(7) Uani 1 1 d . . . . .
C19 C 0.4707(7) 0.71819(18) 0.5366(3) 0.0231(7) Uani 1 1 d . . . . .
C20 C 0.3141(7) 0.67809(18) 0.5048(3) 0.0243(7) Uani 1 1 d . . . . .
H20 H 0.177538 0.690344 0.480189 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3665(8) 0.62009(19) 0.5108(3) 0.0276(8) Uani 1 1 d . . . . .
C22 C 0.5671(8) 0.60018(19) 0.5483(3) 0.0310(9) Uani 1 1 d . . . . .
H22 H 0.596345 0.560223 0.551168 0.037 Uiso 1 1 calc R U . . .
C23 C 0.7219(8) 0.6393(2) 0.5811(3) 0.0315(9) Uani 1 1 d . . . . .
H23 H 0.856131 0.626465 0.607107 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6735(7) 0.69817(19) 0.5747(3) 0.0257(8) 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 C4 1.892(4) . ?
Br2 C9 1.899(5) . ?
N1 C12 1.376(6) . ?
N1 C1 1.385(6) . ?
N1 H1N1 0.8700 . ?
C1 C2 1.400(6) . ?
C1 C6 1.421(6) . ?
C2 C3 1.374(7) . ?
C2 H2 0.9400 . ?
C3 C4 1.405(7) . ?
C3 H3 0.9400 . ?
C4 C5 1.393(6) . ?
C5 C6 1.401(6) . ?
C5 H5 0.9400 . ?
C6 C7 1.454(6) . ?
C7 C8 1.393(6) . ?
C7 C12 1.403(6) . ?
C8 C9 1.397(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.395(8) . ?
C10 C11 1.387(8) . ?
C10 H10 0.9400 . ?
C11 C12 1.400(6) . ?
C11 H11 0.9400 . ?
Br3 C16 1.899(4) . ?
Br4 C21 1.899(5) . ?
N2 C24 1.373(6) . ?
N2 C13 1.385(6) . ?
N2 H2N2 0.8700 . ?
C13 C14 1.390(6) . ?
C13 C18 1.417(6) . ?
C14 C15 1.385(7) . ?
C14 H14 0.9400 . ?
C15 C16 1.401(6) . ?
C15 H15 0.9400 . ?
C16 C17 1.385(6) . ?
C17 C18 1.404(6) . ?
C17 H17 0.9400 . ?
C18 C19 1.448(6) . ?
C19 C20 1.401(6) . ?
C19 C24 1.418(6) . ?
C20 C21 1.378(6) . ?
C20 H20 0.9400 . ?
C21 C22 1.403(6) . ?
C22 C23 1.384(7) . ?
C22 H22 0.9400 . ?
C23 C24 1.393(6) . ?
C23 H23 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C1 108.9(4) . . ?
C12 N1 H1N1 125.5 . . ?
C1 N1 H1N1 125.5 . . ?
N1 C1 C2 129.4(4) . . ?
N1 C1 C6 108.6(4) . . ?
C2 C1 C6 121.9(4) . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 123.0(4) . . ?
C5 C4 Br1 119.3(3) . . ?
C3 C4 Br1 117.8(3) . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 134.1(4) . . ?
C1 C6 C7 106.4(4) . . ?
C8 C7 C12 121.2(4) . . ?
C8 C7 C6 132.5(4) . . ?
C12 C7 C6 106.3(4) . . ?
C7 C8 C9 116.5(4) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 H8 121.8 . . ?
C10 C9 C8 122.7(5) . . ?
C10 C9 Br2 118.2(4) . . ?
C8 C9 Br2 119.1(4) . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 117.3(5) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C11 128.6(5) . . ?
N1 C12 C7 109.8(4) . . ?
C11 C12 C7 121.6(5) . . ?
C24 N2 C13 109.4(4) . . ?
C24 N2 H2N2 125.3 . . ?
C13 N2 H2N2 125.3 . . ?
N2 C13 C14 129.4(4) . . ?
N2 C13 C18 108.7(4) . . ?
C14 C13 C18 122.0(4) . . ?
C15 C14 C13 117.9(4) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 123.1(4) . . ?
C17 C16 Br3 118.8(3) . . ?
C15 C16 Br3 118.1(3) . . ?
C16 C17 C18 116.9(4) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C17 C18 C13 119.9(4) . . ?
C17 C18 C19 133.6(4) . . ?
C13 C18 C19 106.5(4) . . ?
C20 C19 C24 119.6(4) . . ?
C20 C19 C18 134.0(4) . . ?
C24 C19 C18 106.4(4) . . ?
C21 C20 C19 117.9(4) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 122.6(4) . . ?
C20 C21 Br4 119.4(3) . . ?
C22 C21 Br4 118.0(3) . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 118.2(4) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
N2 C24 C23 129.3(4) . . ?
N2 C24 C19 109.0(4) . . ?
C23 C24 C19 121.6(4) . . ?

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
C12 N1 C1 C2 178.5(4) . . . . ?
C12 N1 C1 C6 1.3(5) . . . . ?
N1 C1 C2 C3 -177.9(4) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C2 C3 C4 Br1 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
Br1 C4 C5 C6 180.0(3) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C4 C5 C6 C7 178.7(4) . . . . ?
N1 C1 C6 C5 178.5(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
N1 C1 C6 C7 -0.8(5) . . . . ?
C2 C1 C6 C7 -178.2(4) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C1 C6 C7 C8 178.6(4) . . . . ?
C5 C6 C7 C12 -179.1(4) . . . . ?
C1 C6 C7 C12 0.0(4) . . . . ?
C12 C7 C8 C9 -0.5(6) . . . . ?
C6 C7 C8 C9 -178.9(4) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C7 C8 C9 Br2 179.5(3) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
Br2 C9 C10 C11 -179.4(4) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C1 N1 C12 C11 -179.8(5) . . . . ?
C1 N1 C12 C7 -1.3(5) . . . . ?
C10 C11 C12 N1 177.9(5) . . . . ?
C10 C11 C12 C7 -0.5(7) . . . . ?
C8 C7 C12 N1 -178.0(4) . . . . ?
C6 C7 C12 N1 0.7(5) . . . . ?
C8 C7 C12 C11 0.6(7) . . . . ?
C6 C7 C12 C11 179.4(4) . . . . ?
C24 N2 C13 C14 179.5(5) . . . . ?
C24 N2 C13 C18 -0.5(6) . . . . ?
N2 C13 C14 C15 179.6(5) . . . . ?
C18 C13 C14 C15 -0.4(7) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C14 C15 C16 Br3 179.5(4) . . . . ?
C15 C16 C17 C18 -0.5(7) . . . . ?
Br3 C16 C17 C18 -178.9(3) . . . . ?
C16 C17 C18 C13 -0.5(6) . . . . ?
C16 C17 C18 C19 -179.7(4) . . . . ?
N2 C13 C18 C17 -179.1(4) . . . . ?
C14 C13 C18 C17 0.9(7) . . . . ?
N2 C13 C18 C19 0.3(5) . . . . ?
C14 C13 C18 C19 -179.7(4) . . . . ?
C17 C18 C19 C20 1.4(8) . . . . ?
C13 C18 C19 C20 -177.9(5) . . . . ?
C17 C18 C19 C24 179.2(5) . . . . ?
C13 C18 C19 C24 -0.1(5) . . . . ?
C24 C19 C20 C21 -1.1(6) . . . . ?
C18 C19 C20 C21 176.5(4) . . . . ?
C19 C20 C21 C22 1.0(7) . . . . ?
C19 C20 C21 Br4 -178.6(3) . . . . ?
C20 C21 C22 C23 -0.1(8) . . . . ?
Br4 C21 C22 C23 179.5(4) . . . . ?
C21 C22 C23 C24 -0.8(8) . . . . ?
C13 N2 C24 C23 178.0(5) . . . . ?
C13 N2 C24 C19 0.4(6) . . . . ?
C22 C23 C24 N2 -176.6(5) . . . . ?
C22 C23 C24 C19 0.7(7) . . . . ?
C20 C19 C24 N2 178.0(4) . . . . ?
C18 C19 C24 N2 -0.2(5) . . . . ?
C20 C19 C24 C23 0.2(7) . . . . ?
C18 C19 C24 C23 -178.0(4) . . . . ?

_refine_diff_density_max         2.918
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.241

