#------------------------------------------------------------------------------
#$Date: 2021-06-04 04:03:33 +0300 (Fri, 04 Jun 2021) $
#$Revision: 265761 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/26/1562685.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_1562685
loop_
_publ_author_name
'Koo, Jin Young'
'Kwon, Taeyeon'
'Ahn, Yoolim'
'Choi, Hee Cheul'
_publ_section_title
;
 Phase Change-Driven Radical Population and Electrical Conductivity
 Increases of Organic Radical Crystals by Mild Heating
;
_journal_issue                   20
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              10991
_journal_page_last               10997
_journal_paper_doi               10.1021/acs.jpcc.0c10644
_journal_volume                  125
_journal_year                    2021
_chemical_formula_sum            'C12 H10 Cl1.19 N2 O0.4'
_chemical_formula_weight         230.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 102.511(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.0475(5)
_cell_length_b                   27.970(2)
_cell_length_c                   11.3860(8)
_cell_measurement_reflns_used    19474
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      35.57
_cell_measurement_theta_min      1.456
_cell_volume                     2191.1(3)
_computing_cell_refinement       'APEX2 software Suite'
_computing_data_collection       'APEX2 software Suite'
_computing_data_reduction        'APEX2 software Suite'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Omega and phi scan'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19474
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.574
_diffrn_reflns_theta_min         1.456
_exptl_absorpt_coefficient_mu    0.361
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       Needle
_exptl_crystal_F_000             955
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.664
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         5036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0795
_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)+(0.1034P)²+0.8670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2230
_reflns_number_total             5036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c10644_si_002.cif
_cod_data_source_block           H2PNZ_298K
_cod_depositor_comments
'Adding full bibliography for 1562684--1562685.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C12 H10 Cl1.19 N2 O0.40'
_cod_database_code               1562685
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
Cl01 Cl 0.18935(13) 0.500000 0.86382(6) 0.0507(3) Uani 1 2 d S T P . .
O1W O 0.3789(5) 0.500000 0.1478(3) 0.0649(9) Uani 0.8 2 d S T P . .
Cl02 Cl 0.42438(18) 0.75230(3) 0.36113(9) 0.0695(5) Uani 0.687(3) 1 d . . P . .
N003 N 0.2395(3) 0.500000 0.60140(18) 0.0327(5) Uani 1 2 d S T P . .
H003 H 0.229583 0.499999 0.675356 0.039 Uiso 1 2 calc R U P . .
N004 N 0.2775(3) 0.500000 0.36816(18) 0.0321(5) Uani 1 2 d S T P . .
H004 H 0.290703 0.500000 0.294827 0.039 Uiso 1 2 calc R U P . .
N5 N 0.4809(3) 0.75157(6) 0.1166(2) 0.0467(5) Uani 1 1 d . . . . .
H5 H 0.469332 0.751530 0.190289 0.056 Uiso 1 1 calc R U . . .
C006 C 0.2673(2) 0.45713(6) 0.42465(15) 0.0297(4) Uani 1 1 d . . . . .
C007 C 0.2471(3) 0.45713(6) 0.54544(15) 0.0298(4) Uani 1 1 d . . . . .
C008 C 0.2331(3) 0.41380(7) 0.60450(18) 0.0384(4) Uani 1 1 d . . . . .
H008 H 0.218001 0.413622 0.683636 0.046 Uiso 1 1 calc R U . . .
C009 C 0.2756(3) 0.41353(7) 0.36558(18) 0.0399(4) Uani 1 1 d . . . . .
H009 H 0.288968 0.413092 0.286091 0.048 Uiso 1 1 calc R U . . .
C00B C 0.4903(3) 0.70882(7) 0.0603(2) 0.0426(5) Uani 1 1 d . . . . .
C00C C 0.4893(3) 0.79457(7) 0.0601(2) 0.0464(5) Uani 1 1 d . . . . .
C00D C 0.2640(3) 0.37146(8) 0.4256(2) 0.0468(5) Uani 1 1 d . . . . .
H00D H 0.270878 0.342503 0.386576 0.056 Uiso 1 1 calc R U . . .
C00E C 0.2420(3) 0.37162(8) 0.5446(2) 0.0462(5) Uani 1 1 d . . . . .
H00E H 0.233174 0.342764 0.583637 0.055 Uiso 1 1 calc R U . . .
C00F C 0.4811(3) 0.66525(8) 0.1199(2) 0.0491(6) Uani 1 1 d . . . . .
H00F H 0.468928 0.664829 0.199569 0.059 Uiso 1 1 calc R U . . .
C00G C 0.4766(3) 0.83804(8) 0.1191(3) 0.0536(6) Uani 1 1 d . . . . .
H00G H 0.461077 0.838304 0.198181 0.064 Uiso 1 1 calc R U . . .
C00H C 0.4871(4) 0.88022(8) 0.0593(3) 0.0610(8) Uani 1 1 d . . . . .
H00H H 0.477008 0.909116 0.097899 0.073 Uiso 1 1 calc R U . . .
C00I C 0.4903(4) 0.62318(8) 0.0589(3) 0.0565(7) Uani 1 1 d . . . . .
H00I H 0.483432 0.594222 0.097927 0.068 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.1507 0.1611 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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
C007 N003 C007 123.03(19) . 6_565 ?
C006 N004 C006 122.2(2) 6_565 . ?
C00B N5 C00C 122.4(2) . . ?
N004 C006 C009 121.66(16) . . ?
N004 C006 C007 118.92(15) . . ?
C009 C006 C007 119.42(16) . . ?
N003 C007 C008 121.52(16) . . ?
N003 C007 C006 118.48(15) . . ?
C008 C007 C006 120.00(16) . . ?
C00E C008 C007 119.37(18) . . ?
C00D C009 C006 119.64(18) . . ?
N5 C00B C00F 121.4(2) . . ?
N5 C00B C00B 118.86(13) . 2_655 ?
C00F C00B C00B 119.70(14) . 2_655 ?
N5 C00C C00G 121.5(2) . . ?
N5 C00C C00C 118.70(13) . 2_655 ?
C00G C00C C00C 119.80(15) . 2_655 ?
C009 C00D C00E 120.76(18) . . ?
C008 C00E C00D 120.80(18) . . ?
C00I C00F C00B 119.2(2) . . ?
C00H C00G C00C 119.5(3) . . ?
C00G C00H C00H 120.70(16) . 2_655 ?
C00F C00I C00I 121.14(15) . 2_655 ?
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
N003 C007 1.3644(19) . ?
N003 C007 1.3644(19) 6_565 ?
N004 C006 1.3699(19) 6_565 ?
N004 C006 1.3699(19) . ?
N5 C00B 1.365(3) . ?
N5 C00C 1.371(3) . ?
C006 C009 1.400(2) . ?
C006 C007 1.413(2) . ?
C007 C008 1.400(2) . ?
C008 C00E 1.371(3) . ?
C009 C00D 1.372(3) . ?
C00B C00F 1.403(3) . ?
C00B C00B 1.409(4) 2_655 ?
C00C C00G 1.401(3) . ?
C00C C00C 1.410(5) 2_655 ?
C00D C00E 1.397(3) . ?
C00F C00I 1.375(3) . ?
C00G C00H 1.372(4) . ?
C00H C00H 1.401(6) 2_655 ?
C00I C00I 1.378(5) 2_655 ?
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
C006 N004 C006 C009 179.25(15) 6_565 . . . ?
C006 N004 C006 C007 -0.5(4) 6_565 . . . ?
C007 N003 C007 C008 -178.06(15) 6_565 . . . ?
C007 N003 C007 C006 1.2(4) 6_565 . . . ?
N004 C006 C007 N003 -0.4(3) . . . . ?
C009 C006 C007 N003 179.91(18) . . . . ?
N004 C006 C007 C008 178.95(18) . . . . ?
C009 C006 C007 C008 -0.8(3) . . . . ?
N003 C007 C008 C00E -179.8(2) . . . . ?
C006 C007 C008 C00E 0.9(3) . . . . ?
N004 C006 C009 C00D -179.7(2) . . . . ?
C007 C006 C009 C00D 0.0(3) . . . . ?
C00C N5 C00B C00F -179.89(19) . . . . ?
C00C N5 C00B C00B 0.1(4) . . . 2_655 ?
C00B N5 C00C C00G 179.06(19) . . . . ?
C00B N5 C00C C00C -0.8(4) . . . 2_655 ?
C006 C009 C00D C00E 0.7(3) . . . . ?
C007 C008 C00E C00D -0.2(3) . . . . ?
C009 C00D C00E C008 -0.6(4) . . . . ?
N5 C00B C00F C00I 179.7(2) . . . . ?
C00B C00B C00F C00I -0.3(4) 2_655 . . . ?
N5 C00C C00G C00H 179.5(2) . . . . ?
C00C C00C C00G C00H -0.7(4) 2_655 . . . ?
C00C C00G C00H C00H -0.8(4) . . . 2_655 ?
C00B C00F C00I C00I 0.4(4) . . . 2_655 ?
