#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2212428.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_2212428 loop_ _publ_author_name 'Butt, M. Saeed' 'Akhter, Zareen' 'Bolte, Michael' 'Siddiqui, Humaira M.' 'Ehsan Shamsi' _publ_section_title ; 4-Nitro-N-[4-(4-nitrophenoxy)phenyl]benzamide ; _journal_coeditor_code YM2044 _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o476 _journal_page_last o478 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C19 H13 N3 O6' _chemical_formula_moiety 'C19 H13 N3 O6' _chemical_formula_sum 'C19 H13 N3 O6' _chemical_formula_weight 379.32 _chemical_melting_point 218 _chemical_name_systematic ; 4-Nitro-N-[4-(4-nitrophenoxy)phenyl]benzamide ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.0815(2) _cell_length_b 13.5782(8) _cell_length_c 24.3279(12) _cell_measurement_reflns_used 19637 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.9 _cell_measurement_theta_min 2.3 _cell_volume 1678.57(14) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction X-AREA _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type 'Stoe IPDSII two-circle' _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 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 19554 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.20 _refine_diff_density_min -0.14 _refine_ls_abs_structure_details 'Flack (1983), Friedel pair number ?' _refine_ls_abs_structure_Flack 1.4(9) _refine_ls_extinction_coef 0.047(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 2264 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.06 _refine_ls_R_factor_all 0.030 _refine_ls_R_factor_gt 0.029 _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^)+(0.0528P)^2^+0.1513P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.078 _refine_ls_wR_factor_ref 0.079 _reflns_number_gt 2180 _reflns_number_total 2264 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ym2044.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _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 N N1 0.5383(3) 0.50065(11) 0.32605(5) 0.0382(3) Uani d . 1 O O11 0.3305(3) 0.54604(14) 0.32297(6) 0.0634(5) Uani d . 1 O O12 0.6715(4) 0.47690(10) 0.28625(4) 0.0510(4) Uani d . 1 C C1 0.8533(3) 0.36481(10) 0.53873(6) 0.0249(3) Uani d . 1 O O1 1.0812(2) 0.33727(9) 0.54683(4) 0.0336(3) Uani d . 1 N N2 0.6592(3) 0.36170(10) 0.57693(5) 0.0268(3) Uani d . 1 H H2 0.507(5) 0.3762(17) 0.5662(9) 0.046(6) Uiso d . 1 O O2 0.7498(3) 0.28587(10) 0.80199(4) 0.0391(3) Uani d . 1 N N3 -0.0228(3) 0.10357(9) 0.92925(5) 0.0321(3) Uani d . 1 O O31 -0.1695(3) 0.04335(9) 0.90759(5) 0.0447(3) Uani d . 1 O O32 -0.0415(3) 0.12776(10) 0.97780(5) 0.0455(3) Uani d . 1 C C11 0.6300(3) 0.47200(11) 0.38129(6) 0.0292(3) Uani d . 1 C C12 0.8459(3) 0.41023(11) 0.38582(5) 0.0303(3) Uani d . 1 H H12 0.9429 0.3909 0.3542 0.036 Uiso calc R 1 C C13 0.9163(3) 0.37747(10) 0.43768(6) 0.0281(3) Uani d . 1 H H13 1.0645 0.3355 0.4420 0.034 Uiso calc R 1 C C14 0.7707(3) 0.40576(10) 0.48373(5) 0.0242(3) Uani d . 1 C C15 0.5611(3) 0.47130(11) 0.47812(6) 0.0283(3) Uani d . 1 H H15 0.4677 0.4931 0.5097 0.034 Uiso calc R 1 C C16 0.4890(3) 0.50474(11) 0.42628(6) 0.0311(3) Uani d . 1 H H16 0.3460 0.5491 0.4219 0.037 Uiso calc R 1 C C21 0.6845(3) 0.33624(10) 0.63336(5) 0.0247(3) Uani d . 1 C C22 0.8846(3) 0.27623(12) 0.65337(6) 0.0327(3) Uani d . 1 H H22 1.0108 0.2489 0.6289 0.039 Uiso calc R 1 C C23 0.8987(3) 0.25635(12) 0.70980(6) 0.0350(3) Uani d . 1 H H23 1.0347 0.2155 0.7239 0.042 Uiso calc R 1 C C24 0.7140(3) 0.29648(12) 0.74487(6) 0.0306(3) Uani d . 1 C C25 0.5098(3) 0.35383(12) 0.72519(6) 0.0341(3) Uani d . 1 H H25 0.3810 0.3794 0.7496 0.041 Uiso calc R 1 C C26 0.4950(3) 0.37369(11) 0.66923(6) 0.0315(3) Uani d . 1 H H26 0.3553 0.4129 0.6553 0.038 Uiso calc R 1 C C31 0.5567(3) 0.23850(11) 0.83140(5) 0.0296(3) Uani d . 1 C C32 0.5257(4) 0.26777(12) 0.88616(6) 0.0346(3) Uani d . 1 H H32 0.6331 0.3185 0.9010 0.042 Uiso calc R 1 C C33 0.3384(4) 0.22261(11) 0.91845(6) 0.0331(3) Uani d . 1 H H33 0.3151 0.2417 0.9557 0.040 Uiso calc R 1 C C34 0.1841(3) 0.14874(10) 0.89559(5) 0.0282(3) Uani d . 1 C C35 0.2166(3) 0.11743(11) 0.84176(6) 0.0302(3) Uani d . 1 H H35 0.1104 0.0661 0.8272 0.036 Uiso calc R 1 C C36 0.4075(3) 0.16259(11) 0.80950(5) 0.0305(3) Uani d . 1 H H36 0.4354 0.1416 0.7727 0.037 Uiso calc R 1 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 N1 0.0453(8) 0.0412(7) 0.0282(6) -0.0084(7) -0.0041(6) 0.0075(5) O11 0.0520(9) 0.0952(12) 0.0430(7) 0.0135(9) -0.0078(7) 0.0254(8) O12 0.0792(11) 0.0501(7) 0.0238(5) -0.0022(8) 0.0027(6) -0.0005(5) C1 0.0224(6) 0.0273(6) 0.0252(6) -0.0012(5) -0.0006(5) -0.0009(5) O1 0.0224(5) 0.0467(6) 0.0316(5) 0.0049(5) 0.0012(4) 0.0048(5) N2 0.0207(6) 0.0364(6) 0.0233(5) 0.0020(5) -0.0008(5) 0.0029(5) O2 0.0360(6) 0.0559(7) 0.0255(5) -0.0127(6) -0.0052(4) 0.0092(5) N3 0.0368(7) 0.0306(6) 0.0288(5) 0.0019(6) 0.0028(5) 0.0048(5) O31 0.0509(8) 0.0404(6) 0.0426(6) -0.0148(6) 0.0060(6) -0.0009(5) O32 0.0544(8) 0.0536(7) 0.0285(5) -0.0042(7) 0.0110(6) -0.0013(5) C11 0.0336(8) 0.0301(6) 0.0240(6) -0.0066(6) -0.0026(6) 0.0035(5) C12 0.0332(7) 0.0330(7) 0.0247(6) -0.0036(7) 0.0052(6) -0.0029(5) C13 0.0269(7) 0.0294(6) 0.0282(6) 0.0001(6) 0.0031(6) -0.0019(5) C14 0.0230(6) 0.0260(6) 0.0236(6) -0.0023(6) 0.0003(5) -0.0007(5) C15 0.0275(7) 0.0308(6) 0.0265(6) 0.0033(6) 0.0041(6) 0.0008(5) C16 0.0290(7) 0.0327(7) 0.0317(7) 0.0022(6) 0.0001(6) 0.0048(6) C21 0.0231(6) 0.0282(6) 0.0228(6) -0.0015(6) 0.0002(5) 0.0017(5) C22 0.0286(7) 0.0379(7) 0.0314(7) 0.0075(6) 0.0018(6) 0.0029(6) C23 0.0298(8) 0.0423(8) 0.0329(7) 0.0048(7) -0.0033(6) 0.0109(6) C24 0.0301(7) 0.0373(7) 0.0246(6) -0.0064(6) -0.0026(6) 0.0052(6) C25 0.0332(8) 0.0428(8) 0.0262(6) 0.0038(7) 0.0050(6) 0.0007(6) C26 0.0289(7) 0.0377(7) 0.0279(6) 0.0063(6) 0.0011(6) 0.0038(5) C31 0.0301(7) 0.0341(7) 0.0246(6) -0.0005(6) -0.0025(6) 0.0070(5) C32 0.0414(9) 0.0337(7) 0.0288(6) -0.0068(7) -0.0061(7) 0.0008(6) C33 0.0424(9) 0.0332(7) 0.0237(6) -0.0009(7) -0.0009(6) -0.0011(5) C34 0.0318(7) 0.0282(6) 0.0246(6) 0.0013(6) 0.0006(6) 0.0033(5) C35 0.0350(8) 0.0301(6) 0.0256(6) -0.0013(6) -0.0030(6) -0.0003(5) C36 0.0347(8) 0.0357(7) 0.0211(5) 0.0006(7) -0.0019(6) 0.0012(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 O11 1.225(2) N1 O12 1.225(2) N1 C11 1.4747(18) C1 O1 1.2332(18) C1 N2 1.3557(19) C1 C14 1.5085(18) N2 C21 1.4216(16) N2 H2 0.84(3) O2 C31 1.3741(19) O2 C24 1.4089(16) N3 O31 1.2257(19) N3 O32 1.2297(16) N3 C34 1.467(2) C11 C16 1.382(2) C11 C12 1.386(2) C12 C13 1.385(2) C12 H12 0.9500 C13 C14 1.3966(19) C13 H13 0.9500 C14 C15 1.395(2) C15 C16 1.3895(19) C15 H15 0.9500 C16 H16 0.9500 C21 C22 1.391(2) C21 C26 1.395(2) C22 C23 1.4010(19) C22 H22 0.9500 C23 C24 1.381(2) C23 H23 0.9500 C24 C25 1.383(2) C25 C26 1.3898(19) C25 H25 0.9500 C26 H26 0.9500 C31 C36 1.386(2) C31 C32 1.3992(19) C32 C33 1.378(2) C32 H32 0.9500 C33 C34 1.389(2) C33 H33 0.9500 C34 C35 1.3867(19) C35 C36 1.390(2) C35 H35 0.9500 C36 H36 0.9500 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 O11 N1 O12 124.11(15) ? O11 N1 C11 117.44(15) ? O12 N1 C11 118.45(16) ? O1 C1 N2 124.36(13) ? O1 C1 C14 120.98(13) ? N2 C1 C14 114.66(13) yes C1 N2 C21 127.14(13) yes C1 N2 H2 116.7(15) ? C21 N2 H2 116.2(15) ? C31 O2 C24 117.97(12) yes O31 N3 O32 122.96(15) ? O31 N3 C34 118.36(12) ? O32 N3 C34 118.68(14) ? C16 C11 C12 122.85(13) ? C16 C11 N1 118.25(15) ? C12 C11 N1 118.84(13) ? C13 C12 C11 118.13(13) ? C13 C12 H12 120.9 ? C11 C12 H12 120.9 ? C12 C13 C14 120.38(14) ? C12 C13 H13 119.8 ? C14 C13 H13 119.8 ? C15 C14 C13 120.11(13) ? C15 C14 C1 122.30(12) ? C13 C14 C1 117.57(13) ? C16 C15 C14 119.92(13) ? C16 C15 H15 120.0 ? C14 C15 H15 120.0 ? C11 C16 C15 118.50(14) ? C11 C16 H16 120.7 ? C15 C16 H16 120.7 ? C22 C21 C26 119.95(13) ? C22 C21 N2 123.13(13) ? C26 C21 N2 116.92(12) ? C21 C22 C23 119.55(14) ? C21 C22 H22 120.2 ? C23 C22 H22 120.2 ? C24 C23 C22 119.65(15) ? C24 C23 H23 120.2 ? C22 C23 H23 120.2 ? C23 C24 C25 121.23(13) ? C23 C24 O2 118.77(14) ? C25 C24 O2 119.75(14) ? C24 C25 C26 119.27(14) ? C24 C25 H25 120.4 ? C26 C25 H25 120.4 ? C25 C26 C21 120.30(14) ? C25 C26 H26 119.9 ? C21 C26 H26 119.9 ? O2 C31 C36 122.59(13) ? O2 C31 C32 116.31(14) ? C36 C31 C32 121.03(14) ? C33 C32 C31 119.62(14) ? C33 C32 H32 120.2 ? C31 C32 H32 120.2 ? C32 C33 C34 118.87(13) ? C32 C33 H33 120.6 ? C34 C33 H33 120.6 ? C35 C34 C33 122.17(14) ? C35 C34 N3 118.96(14) ? C33 C34 N3 118.87(13) ? C34 C35 C36 118.74(14) ? C34 C35 H35 120.6 ? C36 C35 H35 120.6 ? C31 C36 C35 119.52(13) ? C31 C36 H36 120.2 ? C35 C36 H36 120.2 ? 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 O1 C1 N2 C21 6.5(2) ? C14 C1 N2 C21 -173.31(13) ? O11 N1 C11 C16 -5.2(2) ? O12 N1 C11 C16 175.59(16) ? O11 N1 C11 C12 172.02(16) ? O12 N1 C11 C12 -7.2(2) ? C16 C11 C12 C13 2.4(2) ? N1 C11 C12 C13 -174.76(14) ? C11 C12 C13 C14 0.5(2) ? C12 C13 C14 C15 -3.3(2) ? C12 C13 C14 C1 178.12(14) ? O1 C1 C14 C15 -154.03(15) ? N2 C1 C14 C15 25.8(2) ? O1 C1 C14 C13 24.6(2) ? N2 C1 C14 C13 -155.60(13) ? C13 C14 C15 C16 3.1(2) ? C1 C14 C15 C16 -178.30(14) ? C12 C11 C16 C15 -2.5(2) ? N1 C11 C16 C15 174.67(14) ? C14 C15 C16 C11 -0.3(2) ? C1 N2 C21 C22 -25.3(2) ? C1 N2 C21 C26 155.33(15) ? C26 C21 C22 C23 -2.0(2) ? N2 C21 C22 C23 178.67(15) ? C21 C22 C23 C24 0.0(3) ? C22 C23 C24 C25 1.9(3) ? C22 C23 C24 O2 -172.20(15) ? C31 O2 C24 C23 -120.83(17) ? C31 O2 C24 C25 65.0(2) ? C23 C24 C25 C26 -1.9(3) ? O2 C24 C25 C26 172.18(15) ? C24 C25 C26 C21 -0.1(2) ? C22 C21 C26 C25 2.0(2) ? N2 C21 C26 C25 -178.58(14) ? C24 O2 C31 C36 32.7(2) yes C24 O2 C31 C32 -150.29(15) yes O2 C31 C32 C33 -179.11(15) ? C36 C31 C32 C33 -2.0(2) ? C31 C32 C33 C34 0.0(2) ? C32 C33 C34 C35 1.5(2) ? C32 C33 C34 N3 -177.44(14) ? O31 N3 C34 C35 -3.9(2) ? O32 N3 C34 C35 176.11(14) ? O31 N3 C34 C33 175.06(15) ? O32 N3 C34 C33 -4.9(2) ? C33 C34 C35 C36 -0.9(2) ? N3 C34 C35 C36 178.03(13) ? O2 C31 C36 C35 179.52(14) ? C32 C31 C36 C35 2.6(2) ? C34 C35 C36 C31 -1.1(2) ? 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 C22 H22 O1 . 0.95 2.36 2.8988(18) 116 N2 H2 O1 1_455 0.84(3) 2.28(3) 3.0449(17) 152(2) C25 H25 O11 2_565 0.95 2.32 3.240(2) 164 C26 H26 O31 3_556 0.95 2.52 3.396(2) 153 C33 H33 O32 4_557 0.95 2.51 3.297(2) 141 C36 H36 O12 4_456 0.95 2.54 3.2329(19) 130 _cod_database_code 2212428