#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006179.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_2006179 loop_ _publ_author_name 'Clegg, W.' 'Elsegood, M. R. J.' 'Jackson, R. F. W.' 'Fraser, J. L.' 'Emsden, L. J.' _publ_section_title ; N-(2,3,5,6-Tetrachloropyrid-4-yl)cinnamide ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 797 _journal_page_last 799 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C14 H8 Cl4 N2 O' _chemical_formula_weight 362.02 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 95.09(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.437(2) _cell_length_b 7.5790(10) _cell_length_c 17.335(2) _cell_measurement_reflns_used 30 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 12.50 _cell_measurement_theta_min 10.94 _cell_volume 1496.7(4) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1988)' _computing_data_reduction 'local programs' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1994)' _diffrn_ambient_temperature 160(2) _diffrn_measurement_device 'Stoe-Siemens diffractometer with Cryostream cooler (Cosier & Glazer, 1986)' _diffrn_measurement_method '\w/\q scans with on-line profile fitting (Clegg, 1981)' _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 0.1090 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3740 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 0.788 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.562 _refine_diff_density_min -0.743 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.061 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_hydrogen_treatment 'riding (see text)' _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2633 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_restrained_S_obs 1.074 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_obs 0.0464 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0549P)^2^+1.8273P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1267 _refine_ls_wR_factor_obs 0.1177 _reflns_number_observed 2245 _reflns_number_total 2633 _reflns_observed_criterion >2\s(I) _[local]_cod_data_source_file ab1474.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2006179 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.0309(14) 0.0252(13) 0.0301(13) -0.0060(11) 0.0077(11) -0.0054(11) C2 0.0266(13) 0.0262(14) 0.0357(14) 0.0011(11) 0.0022(11) -0.0012(11) Cl2 0.0303(4) 0.0544(5) 0.0577(5) 0.0108(3) 0.0016(3) 0.0048(4) C3 0.0348(14) 0.0259(14) 0.0294(14) -0.0003(11) 0.0031(11) 0.0015(11) Cl3 0.0588(5) 0.0496(5) 0.0313(4) 0.0007(4) 0.0029(3) 0.0113(3) N1 0.0341(12) 0.0262(12) 0.0319(12) -0.0029(10) 0.0109(10) 0.0004(10) C4 0.0269(13) 0.0227(13) 0.0356(14) -0.0002(10) 0.0062(12) -0.0024(11) Cl4 0.0269(4) 0.0379(4) 0.0538(5) 0.0047(3) 0.0049(3) -0.0008(3) C5 0.0320(14) 0.0275(14) 0.0260(13) -0.0038(11) 0.0044(11) -0.0020(11) Cl5 0.0507(5) 0.0511(5) 0.0278(4) -0.0019(4) -0.0012(3) 0.0058(3) O 0.0321(10) 0.0365(11) 0.0365(11) -0.0038(8) 0.0125(8) -0.0106(9) N2 0.0229(10) 0.0236(11) 0.0199(10) -0.0085(8) 0.0143(8) -0.0128(8) C6 0.0243(13) 0.0308(14) 0.0261(13) 0.0019(10) 0.0014(11) -0.0023(11) C7 0.0268(13) 0.0319(14) 0.0272(13) 0.0015(11) 0.0066(11) -0.0046(11) C8 0.0278(13) 0.0282(14) 0.0259(13) 0.0026(11) 0.0043(11) -0.0019(11) C9 0.0263(13) 0.0264(13) 0.0275(13) 0.0035(11) 0.0042(10) 0.0029(11) C10 0.0308(14) 0.0329(15) 0.0280(14) -0.0020(11) 0.0065(11) -0.0019(11) C11 0.0439(17) 0.0348(16) 0.0297(14) 0.0025(13) 0.0118(13) -0.0017(12) C12 0.0331(15) 0.0378(16) 0.0362(15) 0.0076(12) 0.0150(12) 0.0120(13) C13 0.0268(14) 0.0379(16) 0.0412(16) -0.0007(12) 0.0051(12) 0.0093(13) C14 0.0299(14) 0.0340(15) 0.0299(14) -0.0016(11) 0.0033(11) 0.0001(12) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.3059(2) 0.3223(3) 0.51630(16) 0.0285(6) Uani d . 1 C C2 0.2735(2) 0.3866(4) 0.44261(16) 0.0295(6) Uani d . 1 C Cl2 0.13344(7) 0.46301(12) 0.41995(5) 0.0476(2) Uani d . 1 Cl C3 0.3580(2) 0.3891(4) 0.38982(15) 0.0300(6) Uani d . 1 C Cl3 0.32432(8) 0.46992(11) 0.29785(4) 0.0466(2) Uani d . 1 Cl N1 0.4666(2) 0.3304(3) 0.40650(13) 0.0303(5) Uani d . 1 N C4 0.4960(2) 0.2687(3) 0.47684(16) 0.0282(6) Uani d . 1 C Cl4 0.63850(6) 0.19321(10) 0.49473(5) 0.0395(2) Uani d . 1 Cl C5 0.4195(2) 0.2626(4) 0.53496(15) 0.0284(6) Uani d . 1 C Cl5 0.46046(7) 0.18428(11) 0.62573(4) 0.0435(2) Uani d . 1 Cl O 0.15025(17) 0.0702(3) 0.52660(11) 0.0345(5) Uani d . 1 O N2 0.22866(17) 0.3258(3) 0.57234(11) 0.0214(5) Uani d . 1 N H2 0.2288 0.4124 0.6062 0.026 Uiso calc R 1 H C6 0.1502(2) 0.1864(4) 0.57327(15) 0.0271(6) Uani d . 1 C C7 0.0751(2) 0.2094(4) 0.63657(16) 0.0284(6) Uani d . 1 C H7 0.0936 0.2955 0.6756 0.034 Uiso calc R 1 H C8 -0.0198(2) 0.1077(4) 0.63875(15) 0.0272(6) Uani d . 1 C H8 -0.0329 0.0232 0.5985 0.033 Uiso calc R 1 H C9 -0.1056(2) 0.1120(3) 0.69624(15) 0.0267(6) Uani d . 1 C C10 -0.0880(2) 0.2073(4) 0.76556(15) 0.0303(6) Uani d . 1 C H10 -0.0169 0.2706 0.7771 0.036 Uiso calc R 1 H C11 -0.1734(3) 0.2098(4) 0.81736(17) 0.0356(7) Uani d . 1 C H11 -0.1607 0.2753 0.8641 0.043 Uiso calc R 1 H C12 -0.2771(3) 0.1176(4) 0.80153(17) 0.0350(7) Uani d . 1 C H12 -0.3357 0.1206 0.8371 0.042 Uiso calc R 1 H C13 -0.2953(3) 0.0205(4) 0.73366(17) 0.0352(7) Uani d . 1 C H13 -0.3661 -0.0442 0.7229 0.042 Uiso calc R 1 H C14 -0.2101(2) 0.0182(4) 0.68153(16) 0.0312(6) Uani d . 1 C H14 -0.2231 -0.0483 0.6351 0.037 Uiso calc R 1 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' O O 0.0106 0.0060 '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 _geom_angle_publ_flag N2 C1 C2 120.7(2) no N2 C1 C5 119.4(2) no C2 C1 C5 119.9(3) no C1 C2 C3 117.9(2) no C1 C2 Cl2 119.8(2) no C3 C2 Cl2 122.3(2) no N1 C3 C2 123.0(3) no N1 C3 Cl3 116.7(2) no C2 C3 Cl3 120.3(2) no C4 N1 C3 118.4(2) no N1 C4 C5 123.7(2) no N1 C4 Cl4 116.2(2) no C5 C4 Cl4 120.1(2) no C1 C5 C4 117.2(2) no C1 C5 Cl5 120.2(2) no C4 C5 Cl5 122.6(2) no C1 N2 C6 116.9(2) yes O C6 N2 120.9(2) yes O C6 C7 129.1(3) yes N2 C6 C7 110.0(2) yes C8 C7 C6 119.1(2) yes C7 C8 C9 127.2(2) yes C14 C9 C10 118.3(3) no C14 C9 C8 118.8(2) no C10 C9 C8 122.9(2) no C11 C10 C9 120.5(3) no C12 C11 C10 120.4(3) no C11 C12 C13 119.9(3) no C14 C13 C12 119.8(3) no C13 C14 C9 121.0(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N2 1.370(3) no C1 C2 1.387(4) no C1 C5 1.387(4) no C2 C3 1.389(4) no C2 Cl2 1.715(3) no C3 N1 1.327(4) no C3 Cl3 1.719(3) no N1 C4 1.322(4) no C4 C5 1.393(4) no C4 Cl4 1.729(3) no C5 Cl5 1.708(3) no O C6 1.196(3) yes N2 C6 1.387(3) yes C6 C7 1.463(4) yes C7 C8 1.334(4) yes C8 C9 1.460(4) no C9 C14 1.395(4) no C9 C10 1.401(4) no C10 C11 1.384(4) no C11 C12 1.383(4) no C12 C13 1.388(4) no C13 C14 1.387(4) no