#------------------------------------------------------------------------------ #$Date: 2008-02-24 08:42:19 +0100 (Sun, 24 Feb 2008) $ #$Revision: 156 $ #$URL: svn://www.crystallography.net/cod/cif/2/2100531.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2100531 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(4-nitrophenyl)-2,3-diaza-1,3-butadiene ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 94.053(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 3.7318(2) _cell_length_b 7.2442(3) _cell_length_c 23.9367(10) _cell_measurement_reflns_used 1479 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.56 _cell_measurement_theta_min 2.94 _cell_volume 645.48(5) _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 0.998 _diffrn_measured_fraction_theta_max 0.989 _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 FR591 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 6443 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.94 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.949 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 308 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.236 _refine_diff_density_min -0.238 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1479 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.3185P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.1101 _reflns_number_gt 1239 _reflns_number_total 1479 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm5032.cif 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_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 O O41 0.4336(3) 1.28743(16) 0.72674(4) 0.0330(3) Uani d . 1 O O42 0.1025(3) 1.38990(14) 0.65597(4) 0.0306(3) Uani d . 1 N N1 0.4502(3) 0.58742(16) 0.50989(5) 0.0218(3) Uani d . 1 N N4 0.2944(3) 1.27087(17) 0.67923(5) 0.0212(3) Uani d . 1 C C1 0.4796(4) 0.77966(19) 0.59139(6) 0.0184(3) Uani d . 1 C C2 0.5886(4) 0.7945(2) 0.64823(5) 0.0200(3) Uani d . 1 C C3 0.5298(4) 0.95619(19) 0.67713(5) 0.0198(3) Uani d . 1 C C4 0.3602(3) 1.10060(18) 0.64832(5) 0.0181(3) Uani d . 1 C C5 0.2477(4) 1.09149(19) 0.59169(6) 0.0191(3) Uani d . 1 C C6 0.3100(3) 0.92931(19) 0.56356(5) 0.0193(3) Uani d . 1 C C7 0.5506(4) 0.60798(19) 0.56165(6) 0.0201(3) Uani d . 1 H H2 0.7037 0.6931 0.6672 0.024 Uiso calc R 1 H H3 0.6041 0.9675 0.7158 0.024 Uiso calc R 1 H H5 0.1320 1.1933 0.5730 0.023 Uiso calc R 1 H H6 0.2368 0.9192 0.5249 0.023 Uiso calc R 1 H H7 0.6735 0.5102 0.5813 0.024 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 O41 0.0403(7) 0.0350(7) 0.0221(5) 0.0060(5) -0.0080(5) -0.0090(5) O42 0.0377(6) 0.0235(6) 0.0297(6) 0.0106(5) -0.0043(5) -0.0031(4) N1 0.0247(6) 0.0182(6) 0.0226(6) 0.0038(5) 0.0021(5) -0.0017(5) N4 0.0201(6) 0.0217(6) 0.0217(6) -0.0002(5) 0.0012(4) -0.0022(5) C1 0.0153(6) 0.0201(7) 0.0201(6) -0.0004(5) 0.0023(5) 0.0003(5) C2 0.0187(7) 0.0214(7) 0.0197(7) 0.0018(5) -0.0003(5) 0.0032(5) C3 0.0182(6) 0.0240(7) 0.0169(6) -0.0013(5) -0.0003(5) 0.0007(5) C4 0.0168(6) 0.0185(7) 0.0192(6) -0.0013(5) 0.0016(5) -0.0032(5) C5 0.0175(6) 0.0190(7) 0.0207(6) 0.0007(5) 0.0007(5) 0.0026(5) C6 0.0189(7) 0.0229(7) 0.0158(6) -0.0004(5) -0.0003(5) -0.0003(5) C7 0.0184(7) 0.0204(7) 0.0215(6) 0.0017(5) 0.0008(5) 0.0013(5) 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 C1 C2 . 1.3963(18) no C1 C6 . 1.4000(19) no C1 C7 . 1.4663(19) no C2 C3 . 1.386(2) no C2 H2 . 0.95 no C3 C4 . 1.3816(19) no C3 H3 . 0.95 no C4 C5 . 1.3919(18) no C4 N4 . 1.4679(17) no C5 C6 . 1.3820(19) no C5 H5 . 0.95 no C6 H6 . 0.95 no N4 O41 . 1.2225(16) no N4 O42 . 1.2288(15) no C7 N1 . 1.2775(18) no C7 H7 . 0.95 no N1 N1 3_666 1.411(2) no 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 C2 C1 C6 . 119.65(12) no C2 C1 C7 . 119.21(12) no C6 C1 C7 . 121.13(12) no C3 C2 C1 . 120.39(12) no C3 C2 H2 . 119.8 no C1 C2 H2 . 119.8 no C4 C3 C2 . 118.29(12) no C4 C3 H3 . 120.9 no C2 C3 H3 . 120.9 no C3 C4 C5 . 123.10(12) no C3 C4 N4 . 118.15(12) no C5 C4 N4 . 118.75(12) no C6 C5 C4 . 117.73(12) no C6 C5 H5 . 121.1 no C4 C5 H5 . 121.1 no C5 C6 C1 . 120.83(12) no C5 C6 H6 . 119.6 no C1 C6 H6 . 119.6 no O41 N4 O42 . 123.26(12) no O41 N4 C4 . 118.43(12) no O42 N4 C4 . 118.31(11) no N1 C7 C1 . 121.27(13) no N1 C7 H7 . 119.4 no C1 C7 H7 . 119.4 no C7 N1 N1 3_666 111.35(14) no 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_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . 0.0(2) no C7 C1 C2 C3 . 179.01(12) no C1 C2 C3 C4 . 0.3(2) no C2 C3 C4 C5 . -0.3(2) no C2 C3 C4 N4 . 179.26(12) no C3 C4 C5 C6 . 0.1(2) no N4 C4 C5 C6 . -179.50(12) no C4 C5 C6 C1 . 0.2(2) no C2 C1 C6 C5 . -0.2(2) no C7 C1 C6 C5 . -179.24(13) no C3 C4 N4 O41 . 9.71(19) no C5 C4 N4 O41 . -170.66(13) no C3 C4 N4 O42 . -170.44(12) no C5 C4 N4 O42 . 9.19(19) no C2 C1 C7 N1 . 178.82(13) no C6 C1 C7 N1 . -2.2(2) no C1 C7 N1 N1 3_666 179.48(13) 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 C3 H3 O41 4_757 0.95 2.50 3.186(2) 129 y C7 H7 O42 1_645 0.95 2.47 3.343(2) 152 y