#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2103108.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_issue '3 Part 2' _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 553 _journal_page_last 563 _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 ; _symmetry_cell_setting triclinic _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 'not measured' _exptl_crystal_density_method 'not measured' _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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.098P)^2^+0.96P] where P=(Fo^2^+2Fc^2^)/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) _[local]_cod_data_source_file bk0105.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_ _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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0176(12) 0.0244(13) 0.0205(12) 0.0050(10) 0.0108(10) 0.0130(11) C2 0.0189(13) 0.0193(13) 0.0206(13) 0.0019(10) 0.0101(10) 0.0084(11) C3 0.0198(13) 0.0244(13) 0.0180(12) 0.0072(10) 0.0118(10) 0.0107(11) C11 0.0230(14) 0.0259(14) 0.0246(14) 0.0046(11) 0.0131(12) 0.0130(12) N11 0.0374(16) 0.0327(15) 0.0326(14) 0.0071(12) 0.0185(13) 0.0200(13) Cl12 0.0437(5) 0.0221(4) 0.0287(4) 0.0000(3) 0.0183(4) 0.0087(3) Cl13 0.0319(4) 0.0300(4) 0.0183(4) 0.0048(3) 0.0133(3) 0.0098(3) C21 0.0175(13) 0.0227(14) 0.0257(14) 0.0019(10) 0.0094(11) 0.0119(12) C22 0.0179(13) 0.0266(14) 0.0225(13) 0.0049(10) 0.0096(11) 0.0138(11) C23 0.0155(12) 0.0257(14) 0.0265(14) 0.0030(10) 0.0088(11) 0.0163(12) C31 0.0342(18) 0.0245(15) 0.0329(17) 0.0018(13) 0.0153(15) 0.0091(13) C32 0.0340(18) 0.042(2) 0.0251(15) 0.0036(15) 0.0134(14) 0.0165(15) C33 0.0307(17) 0.0347(17) 0.0391(18) 0.0041(13) 0.0154(14) 0.0274(15) 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 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 _cod_database_code 2103108