#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2010594.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_2010594 loop_ _publ_author_name 'Cronin, Leroy' 'Adams, Dave A.' 'Nightingale, David J.' 'Clark, James H.' _publ_section_title ; 4-Chloro-N-(4-cyano-2-nitrophenyl)-3-nitrobenzamide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 244 _journal_page_last 245 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C14 H7 Cl1 N4 O5' _chemical_formula_sum 'C14 H7 Cl N4 O5' _chemical_formula_weight 346.69 _chemical_name_systematic ; 4-Chloro-N-(4-cyano-2-nitrophenyl)-3-nitrobenzamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 91.59(16) _cell_angle_beta 112.9(2) _cell_angle_gamma 88.12(8) _cell_formula_units_Z 2 _cell_length_a 7.804(13) _cell_length_b 12.931(6) _cell_length_c 7.49(4) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 9 _cell_volume 696(4) _computing_cell_refinement TEXSAN _computing_data_collection 'TEXSAN (Molecular Structure Corporation, 1993)' _computing_data_reduction TEXSAN _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Rigaku four-circle AFC6' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_sigmaI/netI .0396 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2453 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% 'variation 0.5' _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .312 _exptl_absorpt_correction_T_max .940 _exptl_absorpt_correction_T_min .782 _exptl_absorpt_correction_type 'empirical via \y scans (North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 352 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .24 _refine_diff_density_min -.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.053 _refine_ls_goodness_of_fit_obs 1.092 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 2452 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_restrained_S_obs 1.092 _refine_ls_R_factor_all .088 _refine_ls_R_factor_obs .046 _refine_ls_shift/esd_max .001 _refine_ls_shift/esd_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.1533P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .145 _refine_ls_wR_factor_obs .115 _reflns_number_observed 1747 _reflns_number_total 2453 _reflns_observed_criterion I>2\s(I) _[local]_cod_data_source_file bm1358.cif _[local]_cod_data_source_block I _[local]_cod_chemical_formula_sum_orig 'C14 H7 Cl1 N4 O5' _cod_original_cell_volume 695(4) _cod_database_code 2010594 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 .0491(5) .0239(4) .0773(6) -.0052(3) .0208(4) -.0003(3) O1 .0259(11) .0422(12) .079(2) -.0052(9) .0198(11) -.0050(11) O2 .0403(12) .0245(10) .0609(14) -.0026(8) .0197(10) -.0075(9) N3 .0268(12) .0234(12) .054(2) -.0042(9) .0134(11) -.0017(11) O4 .0384(13) .094(2) .074(2) -.0077(13) .0292(13) .0130(15) O5 .0384(13) .0551(15) .089(2) -.0173(11) .0040(13) -.0209(14) N1 .047(2) .0302(15) .088(2) -.0057(12) .0249(15) -.0093(14) N2 .0298(13) .0288(13) .0395(14) -.0009(10) .0148(10) .0015(10) O3 .0301(11) .0308(11) .0652(15) .0013(9) .0010(10) -.0040(10) N4 .0279(13) .0341(14) .053(2) -.0061(10) .0114(12) .0050(12) C1 .035(2) .028(2) .056(2) -.0021(12) .0180(14) -.0045(13) C2 .036(2) .0237(14) .035(2) -.0040(11) .0134(12) -.0028(11) C3 .035(2) .0287(14) .046(2) .0013(12) .0148(13) -.0037(12) C4 .0243(14) .0316(15) .048(2) -.0046(11) .0142(13) -.0042(12) C5 .0290(14) .0259(13) .032(2) -.0044(11) .0103(11) -.0004(11) C6 .0259(13) .0256(13) .0306(14) -.0018(10) .0103(11) -.0009(11) C7 .0316(15) .0267(14) .038(2) -.0061(11) .0140(12) -.0020(11) C8 .0268(14) .0288(14) .037(2) -.0055(11) .0128(12) -.0018(12) C9 .0270(14) .0275(14) .0308(15) -.0037(11) .0096(11) -.0003(11) C10 .0243(14) .0298(14) .038(2) -.0001(11) .0125(12) -.0007(12) C11 .0238(14) .0304(14) .035(2) -.0056(11) .0104(12) .0029(12) C12 .0318(15) .0243(14) .036(2) -.0036(11) .0113(12) .0006(11) C13 .0274(15) .034(2) .048(2) .0040(12) .0152(13) .0031(13) C14 .0246(14) .0300(14) .041(2) -.0045(11) .0125(12) .0029(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 Cl1 .72328(11) .44652(6) .42411(13) .0512(3) Uani d . 1 Cl O1 -.1103(3) -.1416(2) .0668(3) .0491(6) Uani d . 1 O O2 .0890(3) -.02284(14) .2026(3) .0420(5) Uani d . 1 O N3 .4317(3) -.0462(2) .2098(4) .0355(6) Uani d . 1 N H3A .342(4) -.000(3) .183(5) .043 Uiso d . 1 H O4 1.0909(3) .2578(2) .3301(4) .0663(7) Uani d . 1 O O5 1.0947(3) .3336(2) .5918(4) .0673(8) Uani d . 1 O N1 .2131(4) -.5540(2) .0408(5) .0554(8) Uani d . 1 N N2 .0499(3) -.1114(2) .1366(3) .0323(5) Uani d . 1 N O3 .7448(3) -.0701(2) .3766(3) .0476(6) Uani d . 1 O N4 1.0199(3) .2826(2) .4435(4) .0395(6) Uani d . 1 N C1 .2418(4) -.4673(2) .0663(5) .0393(7) Uani d . 1 C C2 .2846(4) -.3588(2) .0977(4) .0320(6) Uani d . 1 C C3 .4616(4) -.3275(2) .1227(4) .0370(7) Uani d . 1 C H3 .5493(4) -.3762(2) .1161(4) .044 Uiso calc R 1 H C4 .5077(4) -.2251(2) .1570(4) .0345(7) Uani d . 1 C H4 .6258(4) -.2052(2) .1710(4) .041 Uiso calc R 1 H C5 .3797(4) -.1504(2) .1712(4) .0294(6) Uani d . 1 C C6 .1997(3) -.1832(2) .1383(4) .0276(6) Uani d . 1 C C7 .1522(4) -.2861(2) .1031(4) .0318(6) Uani d . 1 C H7 .0327(4) -.3063(2) .0832(4) .038 Uiso calc R 1 H C8 .6100(4) -.0128(2) .3105(4) .0308(6) Uani d . 1 C C9 .6280(3) .1029(2) .3345(4) .0289(6) Uani d . 1 C C10 .8037(4) .1412(2) .3704(4) .0308(6) Uani d . 1 C H10 .9006(4) .0967(2) .3731(4) .037 Uiso calc R 1 H C11 .8316(3) .2456(2) .4015(4) .0301(6) Uani d . 1 C C12 .6897(4) .3150(2) .3955(4) .0312(6) Uani d . 1 C C13 .5151(4) .2765(2) .3598(4) .0361(7) Uani d . 1 C H13 .4180(4) .3214(2) .3554(4) .043 Uiso calc R 1 H C14 .4857(4) .1714(2) .3307(4) .0318(6) Uani d . 1 C H14 .3687(4) .1462(2) .3082(4) .038 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 C8 N3 C5 125.4(3) y O1 N2 O2 122.5(2) y O1 N2 C6 118.3(2) y O2 N2 C6 119.2(2) y O4 N4 O5 124.9(3) y O4 N4 C11 117.3(3) y O5 N4 C11 117.7(3) y N1 C1 C2 177.8(3) y C7 C2 C3 119.9(3) ? C7 C2 C1 120.9(3) ? C3 C2 C1 119.2(3) ? C4 C3 C2 120.5(3) ? C3 C4 C5 120.9(3) ? C4 C5 C6 117.4(2) ? C4 C5 N3 119.8(3) ? C6 C5 N3 122.7(2) ? C7 C6 C5 121.8(3) ? C7 C6 N2 115.6(2) ? C5 C6 N2 122.6(2) ? C6 C7 C2 119.2(3) ? O3 C8 N3 123.9(3) y O3 C8 C9 121.1(3) y N3 C8 C9 114.9(3) y C14 C9 C10 119.1(3) ? C14 C9 C8 124.7(2) ? C10 C9 C8 116.2(2) ? C11 C10 C9 119.2(3) ? C10 C11 C12 122.2(2) ? C10 C11 N4 117.5(2) ? C12 C11 N4 120.3(3) ? C13 C12 C11 118.4(3) ? C13 C12 Cl1 119.7(2) ? C11 C12 Cl1 121.9(2) ? C14 C13 C12 120.0(3) ? C13 C14 C9 121.1(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C12 1.724(3) y O1 N2 1.225(4) y O2 N2 1.234(3) y N3 C8 1.377(5) y N3 C5 1.409(4) y O4 N4 1.213(5) y O5 N4 1.219(6) y N1 C1 1.147(4) y N2 C6 1.465(4) y O3 C8 1.210(4) y N4 C11 1.472(4) y C1 C2 1.445(4) y C2 C7 1.385(4) ? C2 C3 1.392(4) ? C3 C4 1.374(4) ? C4 C5 1.399(4) ? C5 C6 1.406(4) ? C6 C7 1.383(4) ? C8 C9 1.506(4) ? C9 C14 1.390(4) ? C9 C10 1.396(4) ? C10 C11 1.373(4) ? C11 C12 1.390(4) ? C12 C13 1.389(4) ? C13 C14 1.382(4) ?