#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:16:52 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/01/7230153.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_7230153
loop_
_publ_author_name
'Molčanov, Krešimir'
'Stalke, Dietmar'
'Šantić, Ana'
'Demeshko, Serhiy'
'Stilinović, Vladimir'
'Mou, Zhongyu'
'Kertesz, Miklos'
'Kojić-Prodić, Biserka'
_publ_section_title
;
 Probing semiconductivity in crystals of stable semiquinone radicals:
 organic salts of 5,6-dichloro-2,3-dicyanosemiquinone (DDQ) radical anions
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1862
_journal_paper_doi               10.1039/C7CE02146A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C16 H12 Cl2 N3 O2'
_chemical_formula_sum            'C16 H12 Cl2 N3 O2'
_chemical_formula_weight         349.19
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-30T12:12:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3110(3)
_cell_length_b                   13.4662(2)
_cell_length_c                   14.4537(2)
_cell_measurement_reflns_used    4541
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7643
_cell_measurement_theta_min      3.2792
_cell_volume                     3174.71(9)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10832
_diffrn_reflns_theta_full        75.95
_diffrn_reflns_theta_max         75.95
_diffrn_reflns_theta_min         4.26
_exptl_absorpt_coefficient_mu    3.793
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.60486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.048
_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     208
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.7781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2959
_reflns_number_total             3285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce02146a2.cif
_cod_data_source_block           ddq_net2pic
_cod_depositor_comments
'Adding full bibliography for 7230151--7230160.cif.'
_cod_original_sg_symbol_H-M      'P bc n'
_cod_database_code               7230153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.68806(4) 0.91335(4) 0.03468(4) 0.06007(18) Uani d . 1 Cl
Cl2 0.73089(3) 1.13811(4) -0.01095(4) 0.06463(18) Uani d . 1 Cl
O1 0.59369(12) 1.27186(10) 0.02560(12) 0.0665(4) Uani d . 1 O
O2 0.52058(9) 0.88882(9) 0.10585(9) 0.0501(3) Uani d . 1 O
N1 0.40616(15) 1.29939(16) 0.13054(17) 0.0758(6) Uani d . 1 N
N2 0.35738(13) 1.01726(16) 0.20807(14) 0.0633(5) Uani d . 1 N
C1 0.57824(14) 1.18457(13) 0.04724(13) 0.0482(4) Uani d . 1 C
C2 0.50314(13) 1.15564(13) 0.09273(12) 0.0446(4) Uani d . 1 C
C3 0.48453(11) 1.05813(13) 0.11428(11) 0.0413(4) Uani d . 1 C
C4 0.53899(12) 0.97718(12) 0.09123(11) 0.0423(4) Uani d . 1 C
C5 0.61816(12) 1.00751(13) 0.05189(12) 0.0449(4) Uani d . 1 C
C6 0.63655(13) 1.10382(14) 0.03230(13) 0.0468(4) Uani d . 1 C
C7 0.44822(14) 1.23509(14) 0.11477(14) 0.0537(5) Uani d . 1 C
C8 0.41235(14) 1.03419(14) 0.16574(13) 0.0491(4) Uani d . 1 C
N3 0.61203(10) 0.66004(11) 0.22013(11) 0.0445(3) Uani d . 1 N
C9 0.58300(13) 0.66615(15) 0.13267(14) 0.0520(5) Uani d . 1 C
H9 0.5737 0.7282 0.1064 0.062 Uiso calc R 1 H
C10 0.56717(16) 0.58263(16) 0.08244(15) 0.0594(5) Uani d . 1 C
H10 0.5468 0.5874 0.0225 0.071 Uiso calc R 1 H
C11 0.58181(16) 0.49081(16) 0.12174(16) 0.0623(6) Uani d . 1 C
H11 0.5732 0.433 0.0879 0.075 Uiso calc R 1 H
C12 0.60905(15) 0.48604(15) 0.21080(16) 0.0590(5) Uani d . 1 C
H12 0.6171 0.4243 0.2381 0.071 Uiso calc R 1 H
C13 0.62493(12) 0.57116(14) 0.26150(14) 0.0476(4) Uani d . 1 C
C14 0.63529(16) 0.75539(16) 0.26534(17) 0.0617(6) Uani d . 1 C
H14A 0.624 0.7516 0.3311 0.074 Uiso calc R 1 H
H14B 0.6029 0.8091 0.2396 0.074 Uiso calc R 1 H
C15 0.72497(18) 0.7760(2) 0.2503(2) 0.0768(7) Uani d . 1 C
H15A 0.7394 0.8375 0.2797 0.115 Uiso calc R 1 H
H15B 0.7359 0.7806 0.1852 0.115 Uiso calc R 1 H
H15C 0.7569 0.7231 0.2765 0.115 Uiso calc R 1 H
C16 0.65591(18) 0.5660(2) 0.35819(16) 0.0693(6) Uani d . 1 C
H16A 0.6632 0.6321 0.3818 0.104 Uiso calc PR 0.5 H
H16B 0.7075 0.5317 0.3591 0.104 Uiso calc PR 0.5 H
H16C 0.6171 0.5311 0.396 0.104 Uiso calc PR 0.5 H
H16D 0.662 0.4978 0.3761 0.104 Uiso calc PR 0.5 H
H16E 0.6177 0.5982 0.3988 0.104 Uiso calc PR 0.5 H
H16F 0.7081 0.5988 0.362 0.104 Uiso calc PR 0.5 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O1 C1 C2 122.83(19)
O1 C1 C6 122.4(2)
C2 C1 C6 114.76(16)
C3 C2 C7 121.49(18)
C3 C2 C1 123.01(17)
C7 C2 C1 115.50(16)
C2 C3 C8 120.79(17)
C2 C3 C4 121.96(17)
C8 C3 C4 117.14(16)
O2 C4 C3 122.23(18)
O2 C4 C5 122.92(17)
C3 C4 C5 114.83(15)
C6 C5 C4 122.63(17)
C6 C5 Cl1 121.69(16)
C4 C5 Cl1 115.65(13)
C5 C6 C1 122.35(19)
C5 C6 Cl2 121.83(16)
C1 C6 Cl2 115.81(15)
N1 C7 C2 178.1(2)
N2 C8 C3 177.7(2)
C9 N3 C13 121.39(17)
C9 N3 C14 116.53(16)
C13 N3 C14 121.90(17)
N3 C9 C10 120.93(18)
N3 C9 H9 119.5
C10 C9 H9 119.5
C9 C10 C11 119.1(2)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 119.1(2)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C12 C13 121.44(18)
C11 C12 H12 119.3
C13 C12 H12 119.3
N3 C13 C12 117.95(18)
N3 C13 C16 120.57(19)
C12 C13 C16 121.48(19)
N3 C14 C15 110.1(2)
N3 C14 H14A 109.6
C15 C14 H14A 109.6
N3 C14 H14B 109.6
C15 C14 H14B 109.6
H14A C14 H14B 108.2
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C13 C16 H16D 109.5
H16A C16 H16D 141.1
H16B C16 H16D 56.3
H16C C16 H16D 56.3
C13 C16 H16E 109.5
H16A C16 H16E 56.3
H16B C16 H16E 141.1
H16C C16 H16E 56.3
H16D C16 H16E 109.5
C13 C16 H16F 109.5
H16A C16 H16F 56.3
H16B C16 H16F 56.3
H16C C16 H16F 141.1
H16D C16 H16F 109.5
H16E C16 H16F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7232(19)
Cl2 C6 1.724(2)
O1 C1 1.242(2)
O2 C4 1.245(2)
N1 C7 1.128(3)
N2 C8 1.109(3)
C1 C2 1.444(3)
C1 C6 1.461(3)
C2 C3 1.383(2)
C2 C7 1.431(3)
C3 C8 1.429(3)
C3 C4 1.445(2)
C4 C5 1.469(3)
C5 C6 1.361(3)
N3 C9 1.352(3)
N3 C13 1.354(2)
N3 C14 1.490(2)
C9 C10 1.363(3)
C9 H9 0.93
C10 C11 1.382(3)
C10 H10 0.93
C11 C12 1.363(3)
C11 H11 0.93
C12 C13 1.385(3)
C12 H12 0.93
C13 C16 1.488(3)
C14 C15 1.505(4)
C14 H14A 0.97
C14 H14B 0.97
C15 H15A 0.96
C15 H15B 0.96
C15 H15C 0.96
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
C16 H16D 0.96
C16 H16E 0.96
C16 H16F 0.96
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
O1 C1 C2 C3 177.86(19)
C6 C1 C2 C3 -4.8(3)
O1 C1 C2 C7 -2.3(3)
C6 C1 C2 C7 175.07(17)
C7 C2 C3 C8 -4.8(3)
C1 C2 C3 C8 175.09(17)
C7 C2 C3 C4 179.13(17)
C1 C2 C3 C4 -1.0(3)
C2 C3 C4 O2 -175.96(17)
C8 C3 C4 O2 7.8(2)
C2 C3 C4 C5 5.7(2)
C8 C3 C4 C5 -170.54(15)
O2 C4 C5 C6 177.04(17)
C3 C4 C5 C6 -4.6(2)
O2 C4 C5 Cl1 -4.6(2)
C3 C4 C5 Cl1 173.74(12)
C4 C5 C6 C1 -1.2(3)
Cl1 C5 C6 C1 -179.47(14)
C4 C5 C6 Cl2 178.23(13)
Cl1 C5 C6 Cl2 0.0(2)
O1 C1 C6 C5 -176.77(19)
C2 C1 C6 C5 5.9(3)
O1 C1 C6 Cl2 3.8(3)
C2 C1 C6 Cl2 -173.59(13)
C3 C2 C7 N1 -166(8)
C1 C2 C7 N1 14(8)
C2 C3 C8 N2 -65(6)
C4 C3 C8 N2 112(6)
C13 N3 C9 C10 -1.3(3)
C14 N3 C9 C10 173.9(2)
N3 C9 C10 C11 -0.5(4)
C9 C10 C11 C12 2.2(4)
C10 C11 C12 C13 -2.2(4)
C9 N3 C13 C12 1.3(3)
C14 N3 C13 C12 -173.7(2)
C9 N3 C13 C16 -179.2(2)
C14 N3 C13 C16 5.8(3)
C11 C12 C13 N3 0.5(3)
C11 C12 C13 C16 -179.0(2)
C9 N3 C14 C15 -92.8(2)
C13 N3 C14 C15 82.4(3)
