#------------------------------------------------------------------------------
#$Date: 2017-11-15 14:59:14 +0200 (Wed, 15 Nov 2017) $
#$Revision: 203217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/31/2103108.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2103108
loop_
_publ_author_name
'Britton, Doyle'
_publ_section_title
;
 Planar packing of tetrachlorodicyanobenzene isomers
;
_journal_coden_ASTM              ASBSDK
_journal_issue                   3
_journal_name_full
;
 Acta Crystallographica, Section B: Structural Science
;
_journal_page_first              553
_journal_page_last               563
_journal_paper_doi               10.1107/S0108768102003348
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C12 H18, C8 Cl4 N2'
_chemical_formula_sum            'C20 H18 Cl4 N2'
_chemical_formula_weight         428.16
_chemical_name_systematic
;
 para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1
 polymorph I
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL plus manual additions'
_cell_angle_alpha                114.24(3)
_cell_angle_beta                 113.30(2)
_cell_angle_gamma                91.92(3)
_cell_formula_units_Z            1
_cell_length_a                   7.513(3)
_cell_length_b                   8.615(3)
_cell_length_c                   9.029(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    189(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      11
_cell_volume                     475.8(3)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software'
_computing_data_reduction        TEXSAN
_computing_molecular_graphics    'TEXSAN, SHELXTL'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1994)'
_computing_structure_solution    'TEXSAN, MITHRIL, DIRDIF'
_diffrn_ambient_temperature      189(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       'omega-two theta scans'
_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  0.074
_diffrn_reflns_av_sigmaI/netI    0.083
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4293
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_interval_time  '60 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
  DIFABS, Walker, N. and Stuart, D. (1983) Acta Cryst. A39, 158-166.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       sword-shaped
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.647
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.098P)²+0.96P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                2324
_reflns_number_total             2775
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0105.cif
_cod_database_code               2103108
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 0.0391(4) 0.0988(4) -0.0765(4) 0.0190(5) Uani d . 1 C
C2 0.0801(4) 0.1798(4) 0.1069(4) 0.0195(5) Uani d . 1 C
C3 0.0403(4) 0.0797(4) 0.1829(4) 0.0192(5) Uani d . 1 C
C11 0.0763(5) 0.2024(4) -0.1565(4) 0.0231(6) Uani d . 1 C
N11 0.1016(5) 0.2841(4) -0.2219(4) 0.0314(6) Uani d . 1 N
Cl12 0.17471(14) 0.40092(10) 0.23184(11) 0.0321(3) Uani d . 1 Cl
Cl13 0.09077(12) 0.17518(10) 0.40714(10) 0.0265(3) Uani d . 1 Cl
C21 0.4191(4) 0.8209(4) -0.1203(4) 0.0219(6) Uani d . 1 C
C22 0.4591(4) 0.9372(4) -0.1829(4) 0.0212(6) Uani d . 1 C
C23 0.5411(4) 1.1143(4) -0.0630(4) 0.0213(6) Uani d . 1 C
C31 0.3321(6) 0.6276(5) -0.2496(5) 0.0322(7) Uani d . 1 C
H31A 0.3731 0.5943 -0.3443 0.048 Uiso calc PR 0.50 H
H31B 0.1892 0.6045 -0.3021 0.048 Uiso calc PR 0.50 H
H31C 0.3787 0.5613 -0.1843 0.048 Uiso calc PR 0.50 H
H31D 0.2543 0.5791 -0.2095 0.048 Uiso d PR 0.50 H
H31E 0.4381 0.5689 -0.2517 0.048 Uiso d PR 0.50 H
H31F 0.2486 0.6121 -0.3695 0.048 Uiso d PR 0.50 H
C32 0.4074(6) 0.8658(5) -0.3836(5) 0.0334(8) Uani d . 1 C
H32A 0.2984 0.7644 -0.4543 0.050 Uiso calc PR 0.50 H
H32B 0.5213 0.8340 -0.4016 0.050 Uiso calc PR 0.50 H
H32C 0.3701 0.9539 -0.4213 0.050 Uiso calc PR 0.50 H
H32D 0.4948 0.9372 -0.3971 0.050 Uiso d PR 0.50 H
H32E 0.2719 0.8675 -0.4499 0.050 Uiso d PR 0.50 H
H32F 0.4231 0.7477 -0.4302 0.050 Uiso d PR 0.50 H
C33 0.5876(5) 1.2381(5) -0.1296(5) 0.0311(7) Uani d . 1 C
H33A 0.5984 1.3560 -0.0466 0.047 Uiso calc PR 0.50 H
H33B 0.4827 1.2080 -0.2478 0.047 Uiso calc PR 0.50 H
H33C 0.7113 1.2289 -0.1367 0.047 Uiso calc PR 0.50 H
H33D 0.5965 1.1726 -0.2408 0.047 Uiso d PR 0.50 H
H33E 0.7123 1.3206 -0.0396 0.047 Uiso d PR 0.50 H
H33F 0.4836 1.2997 -0.1507 0.047 Uiso d PR 0.50 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 C1 C2 2 . 120.8(3)
C3 C1 C11 2 . 119.5(3)
C2 C1 C11 . . 119.7(3)
C3 C2 C1 . . 119.5(3)
C3 C2 Cl12 . . 121.4(2)
C1 C2 Cl12 . . 119.1(2)
C1 C3 C2 2 . 119.7(3)
C1 C3 Cl13 2 . 119.8(2)
C2 C3 Cl13 . . 120.5(2)
N11 C11 C1 . . 178.6(4)
C23 C21 C22 2_675 . 119.7(3)
C23 C21 C31 2_675 . 119.9(3)
C22 C21 C31 . . 120.4(3)
C23 C22 C21 . . 120.1(3)
C23 C22 C32 . . 120.9(3)
C21 C22 C32 . . 118.9(3)
C22 C23 C21 . 2_675 120.2(3)
C22 C23 C33 . . 120.0(3)
C21 C23 C33 2_675 . 119.8(3)
C21 C31 H31A . . 109.5
C21 C31 H31B . . 109.5
H31A C31 H31B . . 109.5
C21 C31 H31C . . 109.5
H31A C31 H31C . . 109.5
H31B C31 H31C . . 109.5
C21 C31 H31D . . 109.5
H31A C31 H31D . . 141.1
H31B C31 H31D . . 56.3
H31C C31 H31D . . 56.3
C21 C31 H31E . . 109.5
H31A C31 H31E . . 56.3
H31B C31 H31E . . 141.1
H31C C31 H31E . . 56.3
H31D C31 H31E . . 109.5
C21 C31 H31F . . 109.5
H31A C31 H31F . . 56.3
H31B C31 H31F . . 56.3
H31C C31 H31F . . 141.1
H31D C31 H31F . . 109.5
H31E C31 H31F . . 109.5
C22 C32 H32A . . 109.5
C22 C32 H32B . . 109.5
H32A C32 H32B . . 109.5
C22 C32 H32C . . 109.5
H32A C32 H32C . . 109.5
H32B C32 H32C . . 109.5
C22 C32 H32D . . 109.5
H32A C32 H32D . . 141.1
H32B C32 H32D . . 56.3
H32C C32 H32D . . 56.2
C22 C32 H32E . . 109.5
H32A C32 H32E . . 56.3
H32B C32 H32E . . 141.1
H32C C32 H32E . . 56.3
H32D C32 H32E . . 109.5
C22 C32 H32F . . 109.5
H32A C32 H32F . . 56.3
H32B C32 H32F . . 56.3
H32C C32 H32F . . 141.1
H32D C32 H32F . . 109.5
H32E C32 H32F . . 109.5
C23 C33 H33A . . 109.5
C23 C33 H33B . . 109.5
H33A C33 H33B . . 109.5
C23 C33 H33C . . 109.5
H33A C33 H33C . . 109.5
H33B C33 H33C . . 109.5
C23 C33 H33D . . 109.5
H33A C33 H33D . . 141.1
H33B C33 H33D . . 56.3
H33C C33 H33D . . 56.3
C23 C33 H33E . . 109.5
H33A C33 H33E . . 56.3
H33B C33 H33E . . 141.1
H33C C33 H33E . . 56.3
H33D C33 H33E . . 109.5
C23 C33 H33F . . 109.5
H33A C33 H33F . . 56.3
H33B C33 H33F . . 56.3
H33C C33 H33F . . 141.1
H33D C33 H33F . . 109.5
H33E C33 H33F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C3 2 1.384(4)
C1 C2 . 1.399(4)
C1 C11 . 1.439(4)
C2 C3 . 1.391(4)
C2 Cl12 . 1.708(3)
C3 C1 2 1.384(4)
C3 Cl13 . 1.710(3)
C11 N11 . 1.141(4)
C21 C23 2_675 1.407(4)
C21 C22 . 1.412(4)
C21 C31 . 1.513(5)
C22 C23 . 1.391(4)
C22 C32 . 1.525(4)
C23 C21 2_675 1.407(4)
C23 C33 . 1.513(4)
C31 H31A . 0.9600
C31 H31B . 0.9600
C31 H31C . 0.9600
C31 H31D . 0.9600
C31 H31E . 0.9600
C31 H31F . 0.9600
C32 H32A . 0.9600
C32 H32B . 0.9600
C32 H32C . 0.9600
C32 H32D . 0.9600
C32 H32E . 0.9600
C32 H32F . 0.9600
C33 H33A . 0.9600
C33 H33B . 0.9600
C33 H33C . 0.9600
C33 H33D . 0.9600
C33 H33E . 0.9600
C33 H33F . 0.9600
