#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008085.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_2008085 loop_ _publ_author_name 'Hoong-Kun Fun' 'Kandasamy Chinnakali' 'Ibrahim Abdul Razak' 'Zhen Shen' 'Jing-Lin Zuo' 'Xiao-Zeng You' _publ_section_title N,N'-(4,5-Dichloro-o-phenylene)bis(4-tert-butylpyridine-2-carboxamide) _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 99 _journal_page_last 100 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C26 H28 Cl2 N4 O2' _chemical_formula_weight 499.42 _chemical_name_systematic ; 1,2-bis(4-tert-butyl-pyridine-2-carboxamido)-4,5-dichlorobenzene ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL-97 _cell_angle_alpha 104.8070(10) _cell_angle_beta 99.4310(10) _cell_angle_gamma 110.9270(10) _cell_formula_units_Z 2 _cell_length_a 9.38760(10) _cell_length_b 12.4039(2) _cell_length_c 12.7550(3) _cell_measurement_reflns_used 5053 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.05 _cell_measurement_theta_min 1.72 _cell_volume 1286.54(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 0.054 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 9032 _diffrn_reflns_theta_max 27.05 _diffrn_reflns_theta_min 1.72 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_type 'empirical (SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 524 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.376 _refine_diff_density_min -0.273 _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 5102 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.129 _refine_ls_R_factor_gt 0.075 _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^)+(0.0574P)^2^+0.4260P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.176 _reflns_number_gt 3148 _reflns_number_total 5102 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ha1233.cif _[local]_cod_data_source_block ha1233 _cod_database_code 2008085 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 Cl1 0.30221(16) 0.81269(10) 0.04629(10) 0.0859(4) Uani d . 1 . . Cl Cl2 0.60919(13) 0.93142(7) 0.25586(10) 0.0720(4) Uani d . 1 . . Cl O1 0.0892(3) 0.3564(2) -0.1160(2) 0.0766(9) Uani d . 1 . . O O2 0.5725(3) 0.5726(2) 0.3953(2) 0.0630(7) Uani d . 1 . . O N1 0.2201(3) 0.1564(2) -0.0172(2) 0.0434(7) Uani d . 1 . . N N2 0.2897(3) 0.3921(2) 0.0334(2) 0.0438(7) Uani d . 1 . . N H2D 0.3299 0.3541 0.0682 0.053 Uiso calc R 1 . . H N3 0.5612(3) 0.4972(2) 0.2105(2) 0.0427(7) Uani d . 1 . . N H3D 0.5776 0.4437 0.1622 0.051 Uiso calc R 1 . . H N4 0.6735(3) 0.3404(2) 0.2479(2) 0.0470(7) Uani d . 1 . . N C1 -0.1473(6) -0.0967(4) -0.4099(4) 0.0796(13) Uani d . 1 . . C H1A -0.1447 -0.0179 -0.4072 0.119 Uiso calc R 1 . . H H1B -0.2307 -0.1593 -0.4745 0.119 Uiso calc R 1 . . H H1C -0.0471 -0.0977 -0.4158 0.119 Uiso calc R 1 . . H C2 -0.3308(4) -0.1077(4) -0.2877(4) 0.0813(15) Uani d . 1 . . C H2A -0.3209 -0.0273 -0.2853 0.122 Uiso calc R 1 . . H H2B -0.3476 -0.1192 -0.2183 0.122 Uiso calc R 1 . . H H2C -0.4194 -0.1685 -0.3500 0.122 Uiso calc R 1 . . H C3 -0.2016(5) -0.2521(3) -0.3138(4) 0.0767(14) Uani d . 1 . . C H3A -0.2218 -0.2679 -0.2466 0.115 Uiso calc R 1 . . H H3B -0.1074 -0.2622 -0.3238 0.115 Uiso calc R 1 . . H H3C -0.2903 -0.3087 -0.3779 0.115 Uiso calc R 1 . . H C4 -0.1780(4) -0.1205(3) -0.3026(3) 0.0508(9) Uani d . 1 . . C C5 -0.0385(4) -0.0254(3) -0.2016(3) 0.0413(8) Uani d . 1 . . C C6 0.0605(4) -0.0548(3) -0.1316(3) 0.0478(9) Uani d . 1 . . C H6A 0.0428 -0.1364 -0.1447 0.057 Uiso calc R 1 . . H C7 0.1848(4) 0.0369(3) -0.0428(3) 0.0497(9) Uani d . 1 . . C H7A 0.2485 0.0139 0.0024 0.060 Uiso calc R 1 . . H C8 0.1248(4) 0.1847(3) -0.0850(3) 0.0397(8) Uani d . 1 . . C C9 -0.0020(4) 0.0994(3) -0.1754(3) 0.0441(8) Uani d . 1 . . C H9A -0.0637 0.1250 -0.2191 0.053 Uiso calc R 1 . . H C10 0.1643(4) 0.3196(3) -0.0586(3) 0.0452(8) Uani d . 1 . . C C11 0.3632(4) 0.5205(3) 0.0802(3) 0.0388(7) Uani d . 1 . . C C12 0.3055(4) 0.5961(3) 0.0414(3) 0.0493(9) Uani d . 1 . . C H12A 0.2158 0.5621 -0.0202 0.059 Uiso calc R 1 . . H C13 0.3819(5) 0.7224(3) 0.0948(3) 0.0497(9) Uani d . 1 . . C C14 0.5153(4) 0.7740(3) 0.1854(3) 0.0467(9) Uani d . 1 . . C C15 0.5758(4) 0.7000(3) 0.2227(3) 0.0448(8) Uani d . 1 . . C H15A 0.6674 0.7351 0.2830 0.054 Uiso calc R 1 . . H C16 0.5011(4) 0.5737(3) 0.1710(3) 0.0384(7) Uani d . 1 . . C C17 0.5945(4) 0.5035(3) 0.3200(3) 0.0407(8) Uani d . 1 . . C C18 0.6609(3) 0.4138(3) 0.3396(3) 0.0390(7) Uani d . 1 . . C C19 0.7042(3) 0.4114(3) 0.4475(3) 0.0396(8) Uani d . 1 . . C H19A 0.6899 0.4637 0.5074 0.048 Uiso calc R 1 . . H C20 0.7691(3) 0.3313(3) 0.4671(3) 0.0383(7) Uani d . 1 . . C C21 0.7809(4) 0.2543(3) 0.3710(3) 0.0497(9) Uani d . 1 . . C H21A 0.8223 0.1978 0.3779 0.060 Uiso calc R 1 . . H C22 0.7317(5) 0.2613(3) 0.2660(3) 0.0588(10) Uani d . 1 . . C H22A 0.7397 0.2074 0.2039 0.071 Uiso calc R 1 . . H C23 0.8190(4) 0.3226(3) 0.5836(3) 0.0461(8) Uani d . 1 . . C C24 0.6833(6) 0.2181(5) 0.5957(4) 0.0937(16) Uani d . 1 . . C H24A 0.5895 0.2334 0.5866 0.141 Uiso calc R 1 . . H H24B 0.7120 0.2125 0.6693 0.141 Uiso calc R 1 . . H H24C 0.6626 0.1423 0.5389 0.141 Uiso calc R 1 . . H C25 0.9662(5) 0.2960(5) 0.5969(4) 0.0787(13) Uani d . 1 . . C H25A 1.0068 0.3053 0.6744 0.118 Uiso calc R 1 . . H H25B 1.0460 0.3523 0.5750 0.118 Uiso calc R 1 . . H H25C 0.9384 0.2134 0.5497 0.118 Uiso calc R 1 . . H C26 0.8554(7) 0.4416(4) 0.6780(4) 0.0942(17) Uani d . 1 . . C H26A 0.7609 0.4556 0.6748 0.141 Uiso calc R 1 . . H H26B 0.9367 0.5090 0.6687 0.141 Uiso calc R 1 . . H H26C 0.8914 0.4347 0.7499 0.141 Uiso calc R 1 . . 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 Cl1 0.1458(11) 0.0604(6) 0.0738(8) 0.0692(7) 0.0180(7) 0.0288(6) Cl2 0.0946(8) 0.0284(4) 0.0814(8) 0.0169(5) 0.0289(6) 0.0104(5) O1 0.097(2) 0.0424(14) 0.066(2) 0.0300(14) -0.0282(16) 0.0113(13) O2 0.099(2) 0.0646(16) 0.0474(16) 0.0579(16) 0.0223(14) 0.0201(13) N1 0.0470(16) 0.0363(14) 0.0428(17) 0.0182(12) 0.0041(13) 0.0110(12) N2 0.0560(17) 0.0279(12) 0.0392(16) 0.0177(12) -0.0036(13) 0.0090(12) N3 0.0564(16) 0.0338(13) 0.0359(16) 0.0241(12) 0.0052(13) 0.0058(12) N4 0.0574(17) 0.0484(16) 0.0386(17) 0.0310(14) 0.0094(13) 0.0102(13) C1 0.096(3) 0.067(3) 0.051(3) 0.022(2) 0.010(2) 0.005(2) C2 0.048(2) 0.062(3) 0.090(4) 0.013(2) -0.004(2) -0.014(2) C3 0.076(3) 0.0367(19) 0.082(3) 0.0118(19) -0.002(2) -0.003(2) C4 0.048(2) 0.0369(17) 0.051(2) 0.0143(15) 0.0058(17) -0.0006(16) C5 0.0421(18) 0.0361(16) 0.044(2) 0.0166(14) 0.0133(15) 0.0091(15) C6 0.053(2) 0.0337(16) 0.057(2) 0.0221(16) 0.0146(18) 0.0107(16) C7 0.055(2) 0.0414(18) 0.055(2) 0.0264(16) 0.0051(18) 0.0166(17) C8 0.0450(18) 0.0321(15) 0.0394(19) 0.0167(14) 0.0065(15) 0.0106(14) C9 0.0478(19) 0.0376(17) 0.045(2) 0.0210(15) 0.0049(16) 0.0111(15) C10 0.056(2) 0.0356(17) 0.041(2) 0.0208(16) 0.0046(17) 0.0115(15) C11 0.0520(19) 0.0341(15) 0.0326(17) 0.0210(14) 0.0107(15) 0.0115(14) C12 0.069(2) 0.0401(17) 0.042(2) 0.0318(17) 0.0072(17) 0.0127(15) C13 0.079(2) 0.0397(17) 0.047(2) 0.0366(18) 0.0235(19) 0.0209(16) C14 0.066(2) 0.0268(15) 0.046(2) 0.0171(15) 0.0218(18) 0.0092(15) C15 0.053(2) 0.0345(16) 0.043(2) 0.0176(15) 0.0114(16) 0.0088(15) C16 0.0488(18) 0.0345(16) 0.0347(18) 0.0199(14) 0.0117(15) 0.0127(14) C17 0.0435(18) 0.0345(16) 0.0407(19) 0.0177(14) 0.0042(15) 0.0101(15) C18 0.0356(17) 0.0345(16) 0.0400(19) 0.0128(13) 0.0024(14) 0.0097(14) C19 0.0435(18) 0.0375(16) 0.0366(19) 0.0199(14) 0.0072(15) 0.0089(14) C20 0.0327(16) 0.0367(16) 0.0414(19) 0.0128(13) 0.0040(14) 0.0134(14) C21 0.059(2) 0.0450(19) 0.053(2) 0.0316(17) 0.0102(18) 0.0176(17) C22 0.080(3) 0.058(2) 0.048(2) 0.046(2) 0.015(2) 0.0097(18) C23 0.049(2) 0.0515(19) 0.045(2) 0.0258(16) 0.0109(16) 0.0237(17) C24 0.087(3) 0.118(4) 0.088(4) 0.026(3) 0.034(3) 0.071(3) C25 0.075(3) 0.120(4) 0.068(3) 0.060(3) 0.018(2) 0.050(3) C26 0.151(5) 0.088(3) 0.046(3) 0.070(3) -0.001(3) 0.015(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C13 . 1.731(3) ? Cl2 C14 . 1.736(3) ? O1 C10 . 1.213(4) yes O2 C17 . 1.213(4) yes N1 C7 . 1.333(4) yes N1 C8 . 1.341(4) yes N2 C10 . 1.350(4) yes N2 C11 . 1.401(4) yes N3 C17 . 1.357(4) yes N3 C16 . 1.416(4) yes N4 C22 . 1.331(4) yes N4 C18 . 1.337(4) yes C1 C4 . 1.523(6) ? C2 C4 . 1.535(5) ? C3 C4 . 1.532(5) ? C4 C5 . 1.527(4) ? C5 C6 . 1.389(5) ? C5 C9 . 1.394(4) ? C6 C7 . 1.378(4) ? C8 C9 . 1.376(4) ? C8 C10 . 1.510(4) ? C11 C12 . 1.390(4) ? C11 C16 . 1.401(4) ? C12 C13 . 1.387(4) ? C13 C14 . 1.374(5) ? C14 C15 . 1.379(5) ? C15 C16 . 1.384(4) ? C17 C18 . 1.508(4) ? C18 C19 . 1.381(4) ? C19 C20 . 1.389(4) ? C20 C21 . 1.395(5) ? C20 C23 . 1.525(5) ? C21 C22 . 1.379(5) ? C23 C24 . 1.522(5) ? C23 C25 . 1.525(5) ? C23 C26 . 1.530(5) ? 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 C7 N1 C8 115.4(3) C10 N2 C11 129.0(3) C17 N3 C16 123.9(3) C22 N4 C18 115.5(3) C1 C4 C5 108.8(3) C1 C4 C3 109.1(3) C5 C4 C3 112.2(3) C1 C4 C2 109.5(4) C5 C4 C2 109.0(3) C3 C4 C2 108.2(3) C6 C5 C9 115.6(3) C6 C5 C4 123.7(3) C9 C5 C4 120.6(3) C7 C6 C5 120.1(3) N1 C7 C6 124.5(3) N1 C8 C9 124.0(3) N1 C8 C10 116.2(3) C9 C8 C10 119.7(3) C8 C9 C5 120.3(3) O1 C10 N2 124.9(3) O1 C10 C8 122.1(3) N2 C10 C8 113.0(3) C12 C11 C16 119.1(3) C12 C11 N2 123.3(3) C16 C11 N2 117.5(3) C13 C12 C11 119.9(3) C14 C13 C12 120.7(3) C14 C13 Cl1 121.0(3) C12 C13 Cl1 118.3(3) C13 C14 C15 119.9(3) C13 C14 Cl2 121.4(3) C15 C14 Cl2 118.7(3) C14 C15 C16 120.4(3) C15 C16 C11 120.0(3) C15 C16 N3 120.6(3) C11 C16 N3 119.5(3) O2 C17 N3 124.2(3) O2 C17 C18 122.7(3) N3 C17 C18 113.1(3) N4 C18 C19 124.2(3) N4 C18 C17 116.0(3) C19 C18 C17 119.8(3) C18 C19 C20 120.3(3) C19 C20 C21 115.2(3) C19 C20 C23 123.5(3) C21 C20 C23 121.3(3) C22 C21 C20 120.6(3) N4 C22 C21 124.1(3) C24 C23 C20 108.5(3) C24 C23 C25 108.7(3) C20 C23 C25 110.8(3) C24 C23 C26 108.8(4) C20 C23 C26 111.5(3) C25 C23 C26 108.6(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2D N1 1_555 0.86 2.173 2.631(4) 113 no N2 H2D N3 1_555 0.86 2.338 2.745(4) 109 no N3 H3D N4 1_555 0.86 2.206 2.626(4) 110 no C12 H12A O1 1_555 0.93 2.276 2.880(4) 122 yes C25 H25A O1 1_656 0.96 2.501 3.449(5) 170 yes 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 _geom_torsion_publ_flag C1 C4 C5 C6 -117.7(4) ? C3 C4 C5 C6 3.1(5) ? C2 C4 C5 C6 123.0(4) ? C1 C4 C5 C9 61.4(4) ? C3 C4 C5 C9 -177.7(3) ? C2 C4 C5 C9 -57.9(5) ? C9 C5 C6 C7 0.2(5) ? C4 C5 C6 C7 179.4(3) ? C8 N1 C7 C6 -0.1(5) ? C5 C6 C7 N1 -0.1(6) ? C7 N1 C8 C9 0.2(5) ? C7 N1 C8 C10 -179.1(3) ? N1 C8 C9 C5 -0.1(5) ? C10 C8 C9 C5 179.2(3) ? C6 C5 C9 C8 -0.1(5) ? C4 C5 C9 C8 -179.3(3) ? C11 N2 C10 O1 -2.5(6) ? C11 N2 C10 C8 177.3(3) yes N1 C8 C10 O1 178.0(4) ? C9 C8 C10 O1 -1.4(6) ? N1 C8 C10 N2 -1.8(5) yes C9 C8 C10 N2 178.8(3) ? C10 N2 C11 C12 6.0(6) yes C10 N2 C11 C16 -174.5(3) ? C16 C11 C12 C13 -1.8(5) ? N2 C11 C12 C13 177.7(3) ? C11 C12 C13 C14 0.5(6) ? C11 C12 C13 Cl1 -178.1(3) ? C12 C13 C14 C15 1.1(6) ? Cl1 C13 C14 C15 179.6(3) ? C12 C13 C14 Cl2 -178.1(3) ? Cl1 C13 C14 Cl2 0.4(5) ? C13 C14 C15 C16 -1.4(5) ? Cl2 C14 C15 C16 177.8(3) ? C14 C15 C16 C11 0.1(5) ? C14 C15 C16 N3 -178.8(3) ? C12 C11 C16 C15 1.5(5) ? N2 C11 C16 C15 -178.0(3) ? C12 C11 C16 N3 -179.6(3) ? N2 C11 C16 N3 0.9(5) ? C17 N3 C16 C15 51.7(5) yes C17 N3 C16 C11 -127.2(3) ? C16 N3 C17 O2 2.1(5) ? C16 N3 C17 C18 -178.6(3) yes C22 N4 C18 C19 0.2(5) ? C22 N4 C18 C17 -179.8(3) ? O2 C17 C18 N4 177.7(3) ? N3 C17 C18 N4 -1.6(4) yes O2 C17 C18 C19 -2.2(5) ? N3 C17 C18 C19 178.4(3) ? N4 C18 C19 C20 1.6(5) ? C17 C18 C19 C20 -178.4(3) ? C18 C19 C20 C21 -1.9(4) ? C18 C19 C20 C23 -179.6(3) ? C19 C20 C21 C22 0.6(5) ? C23 C20 C21 C22 178.4(3) ? C18 N4 C22 C21 -1.6(5) ? C20 C21 C22 N4 1.2(6) ? C19 C20 C23 C24 95.9(4) ? C21 C20 C23 C24 -81.7(4) ? C19 C20 C23 C25 -144.9(3) ? C21 C20 C23 C25 37.5(4) ? C19 C20 C23 C26 -23.9(5) ? C21 C20 C23 C26 158.5(4) ?