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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/04/8000435.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8000435
loop_
_publ_author_name
'Sun, Huili'
'Ding, Riqing'
'Lv, Shanling'
'Zhou, Shasha'
'Guo, Sidan'
'Qian, Zhaosheng'
'Feng, Hui'
_publ_section_title
;
 Clustering-Triggered Ultralong Room-Temperature Phosphorescence of
 Organic Crystals through Halogen-Mediated Molecular Assembly.
;
_journal_issue                   13
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              4962
_journal_page_last               4969
_journal_paper_doi               10.1021/acs.jpclett.0c01272
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 Br N'
_chemical_formula_sum            'C19 H14 Br N'
_chemical_formula_weight         336.22
_chemical_name_common            9-(4-bromobenzyl)-9H-carbazole
_chemical_name_systematic        9-(4-bromobenzyl)-9H-carbazole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5364(6)
_cell_length_b                   13.6786(14)
_cell_length_c                   19.513(2)
_cell_measurement_reflns_used    7416
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.424
_cell_measurement_theta_min      2.564
_cell_volume                     1477.7(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15866
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.564
_exptl_absorpt_coefficient_mu    2.774
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.6648.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       colorless
_exptl_crystal_F_000             680
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 907 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0312
_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)+(0.0324P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2710
_reflns_number_total             3357
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz0c01272_si_002.cif
_cod_data_source_block           9-(4-bromobenzyl)-9H-carbazole
_cod_depositor_comments
'Adding full bibliography for 8000434--8000435.cif.'
_cod_database_code               8000435
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C9(H9), C5(H5), C15(H15), C4(H4), C16(H16), C19(H19),
 C3(H3), C10(H10), C18(H18), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 -0.66579(10) -0.51260(3) -0.01237(2) 0.07706(18) Uani 1 1 d . . . . .
C1 C -0.6014(5) -0.8209(2) 0.30150(15) 0.0367(6) Uani 1 1 d . . . . .
C11 C -0.8350(6) -1.0043(2) 0.18566(16) 0.0479(7) Uani 1 1 d . . . . .
H11 H -0.7457 -1.0079 0.1454 0.057 Uiso 1 1 calc R . . . .
C17 C -0.5892(6) -0.6166(2) 0.04906(16) 0.0468(7) Uani 1 1 d . . . . .
C6 C -0.7986(5) -0.8576(2) 0.33955(14) 0.0358(6) Uani 1 1 d . . . . .
C12 C -0.7774(5) -0.9372(2) 0.23638(15) 0.0385(6) Uani 1 1 d . . . . .
N1 N -0.5925(4) -0.86835(19) 0.23878(13) 0.0396(6) Uani 1 1 d . . . . .
C14 C -0.4781(5) -0.7672(2) 0.13815(15) 0.0388(6) Uani 1 1 d . . . . .
C8 C -1.1081(5) -0.9941(2) 0.30739(17) 0.0470(7) Uani 1 1 d . . . . .
H8 H -1.2002 -0.9904 0.3472 0.056 Uiso 1 1 calc R . . . .
C9 C -1.1641(7) -1.0605(2) 0.25724(18) 0.0556(8) Uani 1 1 d . . . . .
H9 H -1.2937 -1.1028 0.2636 0.067 Uiso 1 1 calc R . . . .
C5 C -0.8429(7) -0.8217(2) 0.40514(15) 0.0465(7) Uani 1 1 d . . . . .
H5 H -0.9727 -0.8448 0.4307 0.056 Uiso 1 1 calc R . . . .
C15 C -0.3308(6) -0.6859(3) 0.13288(17) 0.0513(8) Uani 1 1 d . . . . .
H15 H -0.1931 -0.6820 0.1600 0.062 Uiso 1 1 calc R . . . .
C4 C -0.6900(8) -0.7511(2) 0.43150(17) 0.0547(8) Uani 1 1 d . . . . .
H4 H -0.7172 -0.7266 0.4753 0.066 Uiso 1 1 calc R . . . .
C16 C -0.3829(7) -0.6102(3) 0.08827(17) 0.0556(8) Uani 1 1 d . . . . .
H16 H -0.2811 -0.5564 0.0848 0.067 Uiso 1 1 calc R . . . .
C7 C -0.9112(5) -0.9320(2) 0.29790(15) 0.0374(6) Uani 1 1 d . . . . .
C19 C -0.6854(6) -0.7701(3) 0.09820(16) 0.0473(7) Uani 1 1 d . . . . .
H19 H -0.7888 -0.8235 0.1016 0.057 Uiso 1 1 calc R . . . .
C3 C -0.4968(7) -0.7163(3) 0.39345(18) 0.0537(8) Uani 1 1 d . . . . .
H3 H -0.3962 -0.6691 0.4125 0.064 Uiso 1 1 calc R . . . .
C10 C -1.0299(6) -1.0657(2) 0.19697(19) 0.0540(8) Uani 1 1 d . . . . .
H10 H -1.0719 -1.1113 0.1637 0.065 Uiso 1 1 calc R . . . .
C13 C -0.4150(5) -0.8510(3) 0.18527(17) 0.0464(7) Uani 1 1 d . . . . .
H13A H -0.3979 -0.9100 0.1582 0.056 Uiso 1 1 calc R . . . .
H13B H -0.2601 -0.8376 0.2065 0.056 Uiso 1 1 calc R . . . .
C18 C -0.7410(6) -0.6950(3) 0.05329(17) 0.0502(8) Uani 1 1 d . . . . .
H18 H -0.8796 -0.6979 0.0264 0.060 Uiso 1 1 calc R . . . .
C2 C -0.4493(6) -0.7499(2) 0.32773(17) 0.0470(8) Uani 1 1 d . . . . .
H2 H -0.3204 -0.7257 0.3023 0.056 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 C1 C6 108.9(2) . . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 N1 129.3(3) . . ?
C10 C11 C12 117.8(3) . . ?
C16 C17 Br1 119.1(3) . . ?
C18 C17 Br1 119.1(2) . . ?
C18 C17 C16 121.8(3) . . ?
C1 C6 C7 106.8(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 133.6(3) . . ?
C11 C12 N1 129.8(3) . . ?
C11 C12 C7 121.3(3) . . ?
N1 C12 C7 108.8(3) . . ?
C1 N1 C12 108.7(2) . . ?
C1 N1 C13 125.5(3) . . ?
C12 N1 C13 125.7(3) . . ?
C15 C14 C19 117.9(3) . . ?
C15 C14 C13 121.3(3) . . ?
C19 C14 C13 120.8(3) . . ?
C9 C8 C7 119.1(3) . . ?
C8 C9 C10 121.0(3) . . ?
C4 C5 C6 118.7(3) . . ?
C16 C15 C14 121.7(3) . . ?
C5 C4 C3 120.8(3) . . ?
C17 C16 C15 118.4(3) . . ?
C12 C7 C6 106.7(2) . . ?
C8 C7 C6 133.8(3) . . ?
C8 C7 C12 119.5(3) . . ?
C18 C19 C14 121.2(3) . . ?
C4 C3 C2 121.8(3) . . ?
C11 C10 C9 121.3(3) . . ?
N1 C13 C14 113.9(2) . . ?
C17 C18 C19 119.0(3) . . ?
C1 C2 C3 117.3(3) . . ?
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 C17 1.908(3) . ?
C1 C6 1.413(4) . ?
C1 N1 1.386(4) . ?
C1 C2 1.383(4) . ?
C11 C12 1.387(4) . ?
C11 C10 1.385(5) . ?
C17 C16 1.377(5) . ?
C17 C18 1.365(5) . ?
C6 C5 1.393(4) . ?
C6 C7 1.444(4) . ?
C12 N1 1.392(4) . ?
C12 C7 1.412(4) . ?
N1 C13 1.454(4) . ?
C14 C15 1.383(5) . ?
C14 C19 1.388(4) . ?
C14 C13 1.510(4) . ?
C8 C9 1.371(5) . ?
C8 C7 1.394(4) . ?
C9 C10 1.393(5) . ?
C5 C4 1.384(5) . ?
C15 C16 1.383(5) . ?
C4 C3 1.386(5) . ?
C19 C18 1.385(5) . ?
C3 C2 1.388(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 63459017
