#------------------------------------------------------------------------------ #$Date: 2011-09-28 16:24:46 +0200 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/05/2100529.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_2100529 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John Nicolson' 'Skakle, Janet M.S.' 'Wardell, James L.' _publ_section_title ; Isomers and polymorphs of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadienes ; _journal_coeditor_code BM5032 _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 666 _journal_page_last 675 _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C14 H10 N4 O4' _chemical_formula_sum 'C14 H10 N4 O4' _chemical_formula_weight 298.26 _chemical_name_systematic ; (E,E)-1,4-Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 105.825(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.0128(4) _cell_length_b 7.6318(5) _cell_length_c 12.8037(5) _cell_measurement_reflns_used 1507 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.55 _cell_measurement_theta_min 3.14 _cell_volume 659.29(6) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO & COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 macro PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker-Nonius FR91 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7854 _diffrn_reflns_theta_full 27.55 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_min 3.14 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 308 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.198 _refine_diff_density_min -0.347 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1507 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0444 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1077 _refine_ls_wR_factor_ref 0.1220 _reflns_number_gt 1095 _reflns_number_total 1507 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm5032.cif _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2100529 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' 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 O O31 -0.09983(16) 0.27543(15) 0.68104(8) 0.0329(3) Uani d . 1 O O32 -0.34487(15) 0.11164(15) 0.59533(9) 0.0359(3) Uani d . 1 N N1 0.41253(17) 0.46167(16) 0.50700(9) 0.0250(3) Uani d . 1 N N3 -0.19378(18) 0.19608(16) 0.59948(10) 0.0254(3) Uani d . 1 C C1 0.1283(2) 0.29160(18) 0.41783(11) 0.0223(3) Uani d . 1 C C2 0.0541(2) 0.28839(19) 0.50926(11) 0.0224(3) Uani d . 1 C C3 -0.1216(2) 0.20250(19) 0.50200(11) 0.0224(3) Uani d . 1 C C4 -0.2296(2) 0.1181(2) 0.40910(12) 0.0267(4) Uani d . 1 C C5 -0.1544(2) 0.1209(2) 0.31907(12) 0.0277(4) Uani d . 1 C C6 0.0221(2) 0.20644(19) 0.32335(11) 0.0260(4) Uani d . 1 C C7 0.3159(2) 0.37952(19) 0.42187(11) 0.0236(3) Uani d . 1 H H2 0.1238 0.3444 0.5748 0.027 Uiso calc R 1 H H4 -0.3506 0.0603 0.4068 0.032 Uiso calc R 1 H H5 -0.2247 0.0636 0.2541 0.033 Uiso calc R 1 H H6 0.0713 0.2071 0.2612 0.031 Uiso calc R 1 H H7 0.3666 0.3755 0.3603 0.028 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 O31 0.0301(6) 0.0435(7) 0.0268(6) -0.0042(5) 0.0105(4) -0.0020(5) O32 0.0262(6) 0.0419(7) 0.0445(7) -0.0069(5) 0.0182(5) 0.0003(5) N1 0.0197(6) 0.0272(7) 0.0308(7) -0.0011(5) 0.0114(5) 0.0007(5) N3 0.0211(7) 0.0266(7) 0.0304(6) 0.0022(5) 0.0103(5) 0.0039(5) C1 0.0220(7) 0.0209(8) 0.0250(7) 0.0029(6) 0.0082(5) 0.0021(6) C2 0.0223(8) 0.0218(8) 0.0237(7) 0.0013(6) 0.0071(5) 0.0002(6) C3 0.0196(7) 0.0245(8) 0.0242(7) 0.0031(6) 0.0077(5) 0.0033(6) C4 0.0184(7) 0.0286(8) 0.0322(8) 0.0001(6) 0.0053(6) 0.0039(6) C5 0.0247(8) 0.0312(9) 0.0239(7) -0.0004(7) 0.0011(5) 0.0005(6) C6 0.0277(8) 0.0286(9) 0.0229(7) 0.0027(6) 0.0087(6) 0.0023(6) C7 0.0229(7) 0.0255(8) 0.0249(7) 0.0031(6) 0.0108(6) 0.0024(6) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 N1 N1 3_666 111.77(13) no N1 C7 C1 . 121.09(12) no N1 C7 H7 . 119.5 no C1 C7 H7 . 119.5 no C6 C1 C2 . 118.86(13) no C6 C1 C7 . 120.36(13) no C2 C1 C7 . 120.76(12) no C3 C2 C1 . 118.69(13) no C3 C2 H2 . 120.7 no C1 C2 H2 . 120.7 no C2 C3 C4 . 123.38(13) no C2 C3 N3 . 117.88(13) no C4 C3 N3 . 118.71(13) no O32 N3 O31 . 123.38(12) no O32 N3 C3 . 118.24(12) no O31 N3 C3 . 118.38(12) no C3 C4 C5 . 117.59(13) no C3 C4 H4 . 121.2 no C5 C4 H4 . 121.2 no C6 C5 C4 . 120.63(14) no C6 C5 H5 . 119.7 no C4 C5 H5 . 119.7 no C5 C6 C1 . 120.85(13) no C5 C6 H6 . 119.6 no C1 C6 H6 . 119.6 no 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 N1 C7 . 1.2797(18) no N1 N1 3_666 1.414(2) no C7 C1 . 1.465(2) no C7 H7 . 0.95 no C1 C6 . 1.396(2) no C1 C2 . 1.4050(19) no C2 C3 . 1.376(2) no C2 H2 . 0.95 no C3 C4 . 1.383(2) no C3 N3 . 1.4699(18) no N3 O32 . 1.2289(16) no N3 O31 . 1.2313(15) no C4 C5 . 1.392(2) no C4 H4 . 0.95 no C5 C6 . 1.387(2) no C5 H5 . 0.95 no C6 H6 . 0.95 no 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 C4 H4 O32 3_456 0.95 2.50 3.448(2) 176 y 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_site_symmetry_1 _geom_torsion _geom_torsion_publ_flag N1 N1 C7 C1 3_666 -179.28(14) no N1 C7 C1 C6 . 178.32(14) no N1 C7 C1 C2 . -3.0(2) no C6 C1 C2 C3 . -0.5(2) no C7 C1 C2 C3 . -179.26(13) no C1 C2 C3 C4 . 0.2(2) no C1 C2 C3 N3 . 178.21(12) no C2 C3 N3 O32 . -176.15(12) no C4 C3 N3 O32 . 1.9(2) no C2 C3 N3 O31 . 3.83(19) no C4 C3 N3 O31 . -178.09(13) no C2 C3 C4 C5 . 0.2(2) no N3 C3 C4 C5 . -177.78(12) no C3 C4 C5 C6 . -0.3(2) no C4 C5 C6 C1 . 0.0(2) no C2 C1 C6 C5 . 0.4(2) no C7 C1 C6 C5 . 179.16(13) no