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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/8/00/04/8000434.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_8000434
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 I N'
_chemical_formula_sum            'C19 H14 I N'
_chemical_formula_weight         383.21
_chemical_name_common            9-(4-Iodobenzyl)-9H-Carbazole
_chemical_name_systematic        9-(4-Iodobenzyl)-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                   5.4967(3)
_cell_length_b                   13.8112(6)
_cell_length_c                   19.8490(9)
_cell_measurement_reflns_used    8905
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.53
_cell_volume                     1506.86(13)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13945
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.527
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0848 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.8372.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       colorless
_exptl_crystal_F_000             752
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0260P)²+0.7184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3107
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz0c01272_si_003.cif
_cod_data_source_block           9-(4-Iodobenzyl)-9H-Carbazole
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 8000434--8000435.cif.
;
_cod_database_code               8000434
_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), C5(H5), C19(H19), C9(H9), C3(H3), C16(H16), C15(H15),
 C2(H2), C4(H4), C18(H18), C10(H10)
;
_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
I1 I 0.66082(8) -0.01120(2) 0.01510(2) 0.06809(13) Uani 1 1 d . . . . .
C11 C 0.8308(8) -0.5067(3) -0.19079(18) 0.0446(8) Uani 1 1 d . . . . .
H11 H 0.7386 -0.5110 -0.1516 0.054 Uiso 1 1 calc R . . . .
C17 C 0.5792(8) -0.1236(3) -0.05289(18) 0.0424(9) Uani 1 1 d . . . . .
C8 C 1.1097(7) -0.4945(3) -0.3095(2) 0.0450(9) Uani 1 1 d . . . . .
H8 H 1.2039 -0.4903 -0.3483 0.054 Uiso 1 1 calc R . . . .
C7 C 0.9128(7) -0.4329(3) -0.30007(18) 0.0354(8) Uani 1 1 d . . . . .
C5 C 0.8471(9) -0.3218(3) -0.40469(18) 0.0455(9) Uani 1 1 d . . . . .
H5 H 0.9769 -0.3449 -0.4301 0.055 Uiso 1 1 calc R . . . .
C6 C 0.8025(7) -0.3581(3) -0.34029(17) 0.0363(8) Uani 1 1 d . . . . .
N1 N 0.5927(5) -0.3700(2) -0.24199(15) 0.0384(7) Uani 1 1 d . . . . .
C12 C 0.7769(6) -0.4390(3) -0.24012(18) 0.0367(8) Uani 1 1 d . . . . .
C19 C 0.6794(9) -0.2752(3) -0.1023(2) 0.0476(9) Uani 1 1 d . . . . .
H19 H 0.7842 -0.3277 -0.1060 0.057 Uiso 1 1 calc R . . . .
C9 C 1.1635(9) -0.5618(3) -0.2607(2) 0.0509(10) Uani 1 1 d . . . . .
H9 H 1.2933 -0.6040 -0.2670 0.061 Uiso 1 1 calc R . . . .
C1 C 0.6034(7) -0.3217(3) -0.30306(18) 0.0366(8) Uani 1 1 d . . . . .
C3 C 0.5012(10) -0.2165(3) -0.3927(2) 0.0530(11) Uani 1 1 d . . . . .
H3 H 0.4002 -0.1694 -0.4111 0.064 Uiso 1 1 calc R . . . .
C16 C 0.3750(9) -0.1171(3) -0.0922(2) 0.0517(10) Uani 1 1 d . . . . .
H16 H 0.2729 -0.0636 -0.0890 0.062 Uiso 1 1 calc R . . . .
C14 C 0.4723(7) -0.2717(3) -0.14248(18) 0.0382(8) Uani 1 1 d . . . . .
C15 C 0.3227(9) -0.1912(3) -0.1370(2) 0.0500(10) Uani 1 1 d . . . . .
H15 H 0.1845 -0.1868 -0.1638 0.060 Uiso 1 1 calc R . . . .
C2 C 0.4535(8) -0.2504(3) -0.3285(2) 0.0467(10) Uani 1 1 d . . . . .
H2 H 0.3247 -0.2260 -0.3033 0.056 Uiso 1 1 calc R . . . .
C13 C 0.4120(7) -0.3535(3) -0.1899(2) 0.0445(9) Uani 1 1 d . . . . .
H13A H 0.3933 -0.4125 -0.1639 0.053 Uiso 1 1 calc R . . . .
H13B H 0.2570 -0.3399 -0.2112 0.053 Uiso 1 1 calc R . . . .
C4 C 0.6954(10) -0.2508(3) -0.4303(2) 0.0532(11) Uani 1 1 d . . . . .
H4 H 0.7240 -0.2259 -0.4731 0.064 Uiso 1 1 calc R . . . .
C18 C 0.7327(8) -0.2019(3) -0.0570(2) 0.0480(10) Uani 1 1 d . . . . .
H18 H 0.8702 -0.2056 -0.0298 0.058 Uiso 1 1 calc R . . . .
C10 C 1.0260(9) -0.5676(3) -0.2017(2) 0.0510(10) Uani 1 1 d . . . . .
H10 H 1.0665 -0.6133 -0.1692 0.061 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'
I I -0.4742 1.8119 '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
C10 C11 C12 117.8(4) . . ?
C16 C17 I1 119.4(3) . . ?
C16 C17 C18 121.4(4) . . ?
C18 C17 I1 119.1(3) . . ?
C9 C8 C7 119.1(4) . . ?
C8 C7 C6 133.9(4) . . ?
C8 C7 C12 119.3(3) . . ?
C12 C7 C6 106.8(3) . . ?
C4 C5 C6 119.0(4) . . ?
C5 C6 C7 133.8(4) . . ?
C5 C6 C1 119.2(4) . . ?
C1 C6 C7 106.9(3) . . ?
C12 N1 C13 125.9(3) . . ?
C1 N1 C12 108.8(3) . . ?
C1 N1 C13 125.2(3) . . ?
C11 C12 C7 121.6(3) . . ?
C11 C12 N1 129.5(3) . . ?
N1 C12 C7 108.8(3) . . ?
C18 C19 C14 121.4(4) . . ?
C8 C9 C10 120.9(4) . . ?
N1 C1 C6 108.6(3) . . ?
C2 C1 C6 121.7(4) . . ?
C2 C1 N1 129.7(4) . . ?
C2 C3 C4 121.8(4) . . ?
C17 C16 C15 119.1(4) . . ?
C19 C14 C13 120.8(4) . . ?
C15 C14 C19 117.9(4) . . ?
C15 C14 C13 121.3(4) . . ?
C16 C15 C14 121.3(4) . . ?
C1 C2 C3 117.7(4) . . ?
N1 C13 C14 114.3(3) . . ?
C5 C4 C3 120.6(4) . . ?
C17 C18 C19 118.9(4) . . ?
C11 C10 C9 121.2(4) . . ?
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 C17 2.106(4) . ?
C11 C12 1.386(5) . ?
C11 C10 1.380(6) . ?
C17 C16 1.370(6) . ?
C17 C18 1.373(6) . ?
C8 C7 1.390(5) . ?
C8 C9 1.374(6) . ?
C7 C6 1.440(5) . ?
C7 C12 1.407(5) . ?
C5 C6 1.395(5) . ?
C5 C4 1.383(6) . ?
C6 C1 1.413(5) . ?
N1 C12 1.391(5) . ?
N1 C1 1.385(5) . ?
N1 C13 1.452(5) . ?
C19 C14 1.390(6) . ?
C19 C18 1.386(6) . ?
C9 C10 1.395(7) . ?
C1 C2 1.380(6) . ?
C3 C2 1.382(6) . ?
C3 C4 1.386(7) . ?
C16 C15 1.384(6) . ?
C14 C15 1.388(6) . ?
C14 C13 1.507(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 65490908
