#------------------------------------------------------------------------------
#$Date: 2017-11-15 14:59:14 +0200 (Wed, 15 Nov 2017) $
#$Revision: 203217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/31/2103106.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_2103106
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
;
 meta 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                118.425(3)
_cell_angle_beta                 109.414(3)
_cell_angle_gamma                95.139(3)
_cell_formula_units_Z            1
_cell_length_a                   7.5290(12)
_cell_length_b                   8.9503(14)
_cell_length_c                   9.0513(11)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.7
_cell_volume                     482.80(12)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  'SHELXTL (Sheldrick, 1994)'
_computing_structure_solution
;
 TEXSAN, MITHRIL, DIRDIF, SHELXTL (Sheldrick, 1994)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
 Siemens SMART area-detectcor diffractometer
;
_diffrn_measurement_method       'omega 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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4996
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_interval_time  '10 hours'
_diffrn_standards_number         120
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS;  Sheldrick, 1996;  Blessing, 1995
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.236
_refine_ls_extinction_coef       0.037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.0590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                1784
_reflns_number_total             2197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0105.cif
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2103106
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl12 0.50548(16) -0.20864(14) 0.15855(14) 0.0379(3) Uani d P 0.50 A -1 Cl
Cl14 0.47371(12) -0.13216(12) -0.40184(12) 0.0339(2) Uani d P 0.50 A -1 Cl
Cl15 0.49291(15) 0.26965(13) -0.16595(15) 0.0368(3) Uani d P 0.50 A -1 Cl
Cl16 0.51453(19) 0.42166(19) 0.23267(16) 0.0364(3) Uani d P 0.50 A -1 Cl
N11 0.5341(4) 0.2301(4) 0.5055(4) 0.0427(6) Uani d P 0.50 A -1 N
N13 0.4777(7) -0.4770(6) -0.2992(5) 0.0405(10) Uani d P 0.50 A -1 N
C1 0.5105(6) 0.1009(7) 0.1736(7) 0.0260(9) Uani d P 0.50 A -1 C
C2 0.5011(6) -0.0772(6) 0.0674(6) 0.0288(8) Uani d P 0.50 A -1 C
C3 0.4934(6) -0.1476(6) -0.1105(7) 0.0263(9) Uani d P 0.50 A -1 C
C4 0.4908(6) -0.0414(5) -0.1812(6) 0.0225(8) Uani d P 0.50 A -1 C
C5 0.4971(5) 0.1357(5) -0.0776(5) 0.0240(7) Uani d P 0.50 A -1 C
C6 0.5054(6) 0.2039(5) 0.1000(6) 0.0237(8) Uani d P 0.50 A -1 C
C11 0.5214(5) 0.1771(4) 0.3620(5) 0.0300(7) Uani d P 0.50 A -1 C
C13 0.4853(4) -0.3316(6) -0.2180(4) 0.0321(7) Uani d P 0.50 A -1 C
C21 -0.0011(2) 0.11360(19) -0.0659(2) 0.0348(3) Uani d . 1 . . C
C22 -0.01445(19) -0.06584(19) -0.18044(18) 0.0337(3) Uani d . 1 . . C
C23 -0.01234(19) -0.17907(18) -0.11388(19) 0.0337(3) Uani d . 1 . . C
C31 -0.0033(3) 0.2354(2) -0.1391(3) 0.0482(4) Uani d . 1 . . C
H31A -0.0632 0.1636 -0.2753 0.072 Uiso calc PR 0.50 . . H
H31B 0.1322 0.3056 -0.0926 0.072 Uiso calc PR 0.50 . . H
H31C -0.0804 0.3157 -0.0965 0.072 Uiso calc PR 0.50 . . H
H31D 0.0556 0.3597 -0.0343 0.072 Uiso calc PR 0.50 . . H
H31E -0.1398 0.2176 -0.2170 0.072 Uiso calc PR 0.50 . . H
H31F 0.0728 0.2076 -0.2130 0.072 Uiso calc PR 0.50 . . H
C32 -0.0315(3) -0.1357(2) -0.3753(2) 0.0475(4) Uani d . 1 . . C
H32A -0.0726 -0.0539 -0.4133 0.071 Uiso calc PR 0.50 . . H
H32B -0.1297 -0.2535 -0.4618 0.071 Uiso calc PR 0.50 . . H
H32C 0.0967 -0.1450 -0.3767 0.071 Uiso calc PR 0.50 . . H
H32D 0.0022 -0.2477 -0.4212 0.071 Uiso calc PR 0.50 . . H
H32E 0.0593 -0.0481 -0.3728 0.071 Uiso calc PR 0.50 . . H
H32F -0.1671 -0.1566 -0.4578 0.071 Uiso calc PR 0.50 . . H
C33 -0.0273(3) -0.3734(2) -0.2370(2) 0.0486(4) Uani d . 1 . . C
H33A -0.0736 -0.4060 -0.3662 0.073 Uiso calc PR 0.50 . . H
H33B -0.1208 -0.4487 -0.2281 0.073 Uiso calc PR 0.50 . . H
H33C 0.1027 -0.3906 -0.1960 0.073 Uiso calc PR 0.50 . . H
H33D 0.0125 -0.4242 -0.1606 0.073 Uiso calc PR 0.50 . . H
H33E 0.0597 -0.3815 -0.2987 0.073 Uiso calc PR 0.50 . . H
H33F -0.1638 -0.4396 -0.3309 0.073 Uiso calc 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
C6 C1 C2 . . 119.4(4)
C6 C1 C11 . . 120.0(4)
C2 C1 C11 . . 120.5(4)
C1 C2 C3 . . 120.1(3)
C1 C2 Cl12 . . 119.8(3)
C3 C2 Cl12 . . 120.2(4)
C4 C3 C2 . . 119.6(4)
C4 C3 C13 . . 121.0(4)
C2 C3 C13 . . 119.4(4)
C3 C4 C5 . . 120.8(4)
C3 C4 Cl14 . . 118.8(3)
C5 C4 Cl14 . . 120.4(3)
C4 C5 C6 . . 118.8(4)
C4 C5 Cl15 . . 121.1(3)
C6 C5 Cl15 . . 120.2(3)
C1 C6 C5 . . 121.3(4)
C1 C6 Cl16 . . 118.5(4)
C5 C6 Cl16 . . 120.3(3)
N11 C11 C1 . . 177.0(4)
N13 C13 C3 . . 178.1(4)
C23 C21 C22 2 . 120.23(13)
C23 C21 C31 2 . 120.32(13)
C22 C21 C31 . . 119.45(13)
C23 C22 C21 . . 119.79(13)
C23 C22 C32 . . 120.41(13)
C21 C22 C32 . . 119.80(14)
C22 C23 C21 . 2 119.98(12)
C22 C23 C33 . . 120.12(14)
C21 C23 C33 2 . 119.90(14)
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 . . 56.3
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
Cl12 C2 . 1.726(4)
Cl14 C4 . 1.712(4)
Cl15 C5 . 1.726(4)
Cl16 C6 . 1.714(4)
N11 C11 . 1.115(4)
N13 C13 . 1.134(5)
C1 C6 . 1.367(5)
C1 C2 . 1.395(6)
C1 C11 . 1.473(6)
C2 C3 . 1.400(6)
C3 C4 . 1.374(5)
C3 C13 . 1.442(6)
C4 C5 . 1.391(5)
C5 C6 . 1.398(6)
C21 C23 2 1.405(2)
C21 C22 . 1.408(2)
C21 C31 . 1.520(2)
C22 C23 . 1.403(2)
C22 C32 . 1.5180(19)
C23 C21 2 1.405(2)
C23 C33 . 1.521(2)
C31 H31A . 0.9800
C31 H31B . 0.9800
C31 H31C . 0.9800
C31 H31D . 0.9800
C31 H31E . 0.9800
C31 H31F . 0.9800
C32 H32A . 0.9800
C32 H32B . 0.9800
C32 H32C . 0.9800
C32 H32D . 0.9800
C32 H32E . 0.9800
C32 H32F . 0.9800
C33 H33A . 0.9800
C33 H33B . 0.9800
C33 H33C . 0.9800
C33 H33D . 0.9800
C33 H33E . 0.9800
C33 H33F . 0.9800
