#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:00:51 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237504.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_7237504
loop_
_publ_author_name
'Abdurahman, Alim'
'Chen, Yingxin'
'Ai, Xin'
'Ablikim, Obolda'
'Gao, Yu'
'Dong, Shengzhi'
'Li, Bao'
'Yang, Bing'
'Zhang, Ming'
'Li, Feng'
_publ_section_title
;
 A pure red luminescent β-carboline-substituted biphenylmethyl radical:
 photophysics, stability and OLEDs
;
_journal_issue                   42
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              11248
_journal_paper_doi               10.1039/C8TC04298E
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C25 H12 Cl6 N'
_chemical_formula_sum            'C24 H11 Cl6 N2'
_chemical_formula_weight         540.05
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-23 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6879(5)
_cell_length_b                   8.2499(2)
_cell_length_c                   17.2222(5)
_cell_measurement_reflns_used    327
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.2495
_cell_measurement_theta_min      4.5842
_cell_volume                     2258.08(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Mercury2 (2x2 bin mode)
;
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25386
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.0500
_exptl_crystal_size_mid          0.0300
_exptl_crystal_size_min          0.0200
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+1.2449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1669
_reflns_number_gt                3293
_reflns_number_total             5592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8tc04298e2.cif
_cod_data_source_block           a
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7237504
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.30351(7) 0.89322(12) 0.24686(5) 0.0676(3) Uani 1 1 d .
Cl2 Cl 0.20483(6) 0.28209(10) 0.36841(7) 0.0711(3) Uani 1 1 d .
Cl3 Cl 0.11023(6) 0.91669(10) 0.33933(7) 0.0743(3) Uani 1 1 d .
Cl4 Cl 0.27079(7) 0.64871(13) 0.53014(6) 0.0727(3) Uani 1 1 d .
Cl5 Cl 0.43713(7) 1.19981(12) 0.52870(7) 0.0776(3) Uani 1 1 d .
Cl6 Cl -0.09154(7) 0.46117(16) 0.39563(10) 0.1001(4) Uani 1 1 d .
C2 C 0.3049(2) 0.7933(4) 0.4743(2) 0.0491(7) Uani 1 1 d .
C1 C 0.28826(18) 0.7744(3) 0.38986(19) 0.0434(7) Uani 1 1 d .
C6 C 0.32266(19) 0.8950(4) 0.35133(19) 0.0465(7) Uani 1 1 d .
C3 C 0.3510(2) 0.9211(4) 0.5175(2) 0.0529(8) Uani 1 1 d .
H3A H 0.3612 0.9293 0.5736 0.063 Uiso 1 1 calc R
C4 C 0.3817(2) 1.0360(4) 0.4761(2) 0.0524(8) Uani 1 1 d .
C5 C 0.3689(2) 1.0244(4) 0.3934(2) 0.0513(8) Uani 1 1 d .
H5A H 0.3908 1.1019 0.3663 0.062 Uiso 1 1 calc R
C7 C 0.23640(19) 0.6431(3) 0.34434(18) 0.0437(7) Uani 1 1 d .
C8 C 0.15579(19) 0.5981(3) 0.35403(18) 0.0440(7) Uani 1 1 d .
C9 C 0.0942(2) 0.7137(4) 0.3559(2) 0.0531(8) Uani 1 1 d .
C12 C 0.0577(2) 0.3936(4) 0.3737(2) 0.0578(9) Uani 1 1 d .
H12A H 0.0451 0.2851 0.3788 0.069 Uiso 1 1 calc R
C13 C 0.1331(2) 0.4366(4) 0.3632(2) 0.0503(7) Uani 1 1 d .
C10 C 0.0189(2) 0.6737(4) 0.3680(2) 0.0636(10) Uani 1 1 d .
H10A H -0.0194 0.7540 0.3702 0.076 Uiso 1 1 calc R
C11 C 0.0011(2) 0.5128(5) 0.3768(2) 0.0630(9) Uani 1 1 d .
N1 N 0.26540(16) 0.5554(3) 0.28969(16) 0.0474(6) Uani 1 1 d .
C16 C 0.3494(3) 0.3977(4) 0.2369(3) 0.0653(10) Uani 1 1 d .
C15 C 0.3473(2) 0.4923(4) 0.3041(2) 0.0529(8) Uani 1 1 d .
C17 C 0.2672(3) 0.4057(4) 0.1788(2) 0.0692(11) Uani 1 1 d .
C18 C 0.2168(2) 0.5053(4) 0.2118(2) 0.0557(9) Uani 1 1 d .
C14 C 0.4173(2) 0.5058(5) 0.3722(3) 0.0660(10) Uani 1 1 d .
H14A H 0.4139 0.5656 0.4168 0.079 Uiso 1 1 calc R
C19 C 0.1358(3) 0.5479(5) 0.1679(2) 0.0708(11) Uani 1 1 d .
H19A H 0.1043 0.6150 0.1908 0.085 Uiso 1 1 calc R
N2 N 0.4916(2) 0.4324(5) 0.3746(3) 0.1029(14) Uani 1 1 d .
C20 C 0.1027(3) 0.4909(6) 0.0911(3) 0.0880(15) Uani 1 1 d .
H20A H 0.0481 0.5184 0.0607 0.106 Uiso 1 1 calc R
C23 C 0.4255(4) 0.3201(5) 0.2405(4) 0.0943(17) Uani 1 1 d .
H23A H 0.4295 0.2554 0.1976 0.113 Uiso 1 1 calc R
C21 C 0.1497(5) 0.3935(8) 0.0591(3) 0.119(2) Uani 1 1 d .
H21A H 0.1257 0.3562 0.0061 0.142 Uiso 1 1 calc R
C24 C 0.4935(4) 0.3417(7) 0.3083(5) 0.1052(18) Uani 1 1 d .
H24A H 0.5440 0.2922 0.3095 0.126 Uiso 1 1 calc R
C22 C 0.2310(4) 0.3458(7) 0.1001(3) 0.106(2) Uani 1 1 d .
H22A H 0.2605 0.2764 0.0761 0.127 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/c8tc04298e. 2018
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C2 C1 123.0(3)
C3 C2 Cl4 116.7(3)
C1 C2 Cl4 120.3(2)
C2 C1 C6 115.4(3)
C2 C1 C7 122.5(3)
C6 C1 C7 122.1(3)
C5 C6 C1 122.6(3)
C5 C6 Cl1 116.6(2)
C1 C6 Cl1 120.7(2)
C4 C3 C2 118.7(3)
C3 C4 C5 121.6(3)
C3 C4 Cl5 119.3(3)
C5 C4 Cl5 119.1(3)
C4 C5 C6 118.7(3)
N1 C7 C8 118.2(3)
N1 C7 C1 118.7(3)
C8 C7 C1 123.1(3)
C13 C8 C9 114.5(3)
C13 C8 C7 123.0(3)
C9 C8 C7 122.4(3)
C10 C9 C8 123.1(3)
C10 C9 Cl3 116.8(3)
C8 C9 Cl3 120.0(2)
C13 C12 C11 119.3(3)
C12 C13 C8 123.3(3)
C12 C13 Cl2 116.7(2)
C8 C13 Cl2 119.8(2)
C9 C10 C11 119.1(3)
C12 C11 C10 120.6(3)
C12 C11 Cl6 119.7(3)
C10 C11 Cl6 119.6(3)
C7 N1 C18 125.7(3)
C7 N1 C15 126.3(3)
C18 N1 C15 107.8(3)
C15 C16 C23 117.8(4)
C15 C16 C17 106.9(3)
C23 C16 C17 135.3(4)
C14 C15 C16 121.0(3)
C14 C15 N1 129.9(3)
C16 C15 N1 109.0(3)
C22 C17 C18 117.6(5)
C22 C17 C16 134.5(5)
C18 C17 C16 107.8(3)
C19 C18 N1 129.3(3)
C19 C18 C17 122.1(4)
N1 C18 C17 108.4(3)
N2 C14 C15 120.9(4)
C20 C19 C18 119.2(5)
C14 N2 C24 117.8(5)
C21 C20 C19 119.4(5)
C24 C23 C16 118.7(4)
C20 C21 C22 124.2(5)
C23 C24 N2 123.8(5)
C21 C22 C17 117.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.729(3)
Cl2 C13 1.732(3)
Cl3 C9 1.733(3)
Cl4 C2 1.733(3)
Cl5 C4 1.730(3)
Cl6 C11 1.727(3)
C2 C3 1.382(4)
C2 C1 1.404(4)
C1 C6 1.412(4)
C1 C7 1.457(4)
C6 C5 1.385(4)
C3 C4 1.376(5)
C4 C5 1.377(5)
C7 N1 1.386(4)
C7 C8 1.453(4)
C8 C13 1.407(4)
C8 C9 1.409(4)
C9 C10 1.375(5)
C12 C13 1.370(5)
C12 C11 1.377(5)
C10 C11 1.379(5)
N1 C18 1.401(4)
N1 C15 1.411(4)
C16 C15 1.405(5)
C16 C23 1.408(6)
C16 C17 1.432(6)
C15 C14 1.384(5)
C17 C22 1.396(6)
C17 C18 1.412(5)
C18 C19 1.378(5)
C14 N2 1.368(5)
C19 C20 1.353(6)
N2 C24 1.374(8)
C20 C21 1.353(8)
C23 C24 1.370(8)
C21 C22 1.383(9)
