#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202463.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_2202463 loop_ _publ_author_name 'Jose Kavitha, Savaridasson' 'Srinivasan Chandrasekar' 'Panchanatheswaran, Krishnaswamy' _publ_section_title ; trans-1,2-Bis(3-chlorophenyl)diazene oxide ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o947 _journal_page_last o949 _journal_paper_doi 10.1107/S1600536803012200 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C12 H8 Cl2 N2 O' _chemical_formula_sum 'C12 H8 Cl2 N2 O' _chemical_formula_weight 267.10 _chemical_melting_point 367.5(5) _chemical_name_common 3,3'-dichloroazobenzene _chemical_name_systematic ; trans-Bis(3-chlorophenyl)diazine oxide ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.155(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 3.911(5) _cell_length_b 5.893(5) _cell_length_c 25.367(5) _cell_measurement_reflns_used 1179 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.55 _cell_measurement_theta_min 3.22 _cell_volume 583.1(9) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1983)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Atomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _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 0.71069 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 1179 _diffrn_reflns_theta_full 24.95 _diffrn_reflns_theta_max 24.95 _diffrn_reflns_theta_min 3.22 _diffrn_standards_decay_% neglible _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.539 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.213 _refine_diff_density_min -0.230 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 1021 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0476 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.3370P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1266 _refine_ls_wR_factor_ref 0.1396 _reflns_number_gt 807 _reflns_number_total 1021 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6229.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '367-368 K' was changed to '367.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '367-368 K' was changed to '367.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202463 _cod_database_fobs_code 2202463 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_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 0.3752(2) 0.3764(2) 0.29551(3) 0.0852(4) Uani d . 1 . . Cl O1 0.7582(14) 0.7545(8) 0.52152(16) 0.0767(14) Uani d P 0.50 . . O N1 0.5810(7) 0.5880(4) 0.49375(9) 0.0594(7) Uani d . 1 . . N C1 0.6025(7) 0.6347(5) 0.43800(11) 0.0525(7) Uani d . 1 . . C C2 0.4869(7) 0.4899(5) 0.39766(9) 0.0462(6) Uani d . 1 . . C H2 0.3863 0.3516 0.4050 0.055 Uiso calc R 1 . . H C3 0.5245(7) 0.5552(5) 0.34645(10) 0.0500(7) Uani d . 1 . . C C4 0.6758(8) 0.7591(7) 0.33474(15) 0.0689(10) Uani d . 1 . . C H4 0.7005 0.8004 0.2998 0.083 Uiso calc R 1 . . H C5 0.7886(9) 0.8994(6) 0.3753(2) 0.0815(12) Uani d . 1 . . C H5 0.8904 1.0372 0.3678 0.098 Uiso calc R 1 . . H C6 0.7538(9) 0.8399(6) 0.42696(16) 0.0702(10) Uani d . 1 . . C H6 0.8310 0.9366 0.4543 0.084 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 0.0925(7) 0.1179(9) 0.0432(5) 0.0156(6) -0.0083(4) -0.0249(5) O1 0.116(4) 0.069(3) 0.045(2) -0.043(3) 0.003(2) -0.008(2) N1 0.0684(17) 0.0669(17) 0.0417(13) 0.0107(13) -0.0051(11) -0.0121(13) C1 0.0526(16) 0.0594(18) 0.0445(15) 0.0138(15) -0.0033(12) -0.0097(13) C2 0.0518(15) 0.0471(15) 0.0400(14) 0.0014(13) 0.0048(11) 0.0004(12) C3 0.0478(15) 0.0627(18) 0.0394(14) 0.0098(13) 0.0018(11) 0.0011(13) C4 0.0593(18) 0.077(2) 0.072(2) 0.0133(17) 0.0186(16) 0.0311(19) C5 0.066(2) 0.052(2) 0.126(4) -0.0037(17) 0.009(2) 0.021(2) C6 0.0617(19) 0.055(2) 0.091(3) 0.0027(16) -0.0122(18) -0.0190(18) 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' Cl Cl 0.1484 0.1585 '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_1 _geom_angle _geom_angle_publ_flag N1 N1 O1 3_666 134.6(3) y N1 N1 C1 3_666 117.7(3) y O1 N1 C1 . 107.7(3) y C2 C1 C6 . 120.7(3) y C2 C1 N1 . 124.5(3) y C6 C1 N1 . 114.8(3) y C3 C2 C1 . 118.4(3) y C3 C2 H2 . 120.8 ? C1 C2 H2 . 120.8 ? C2 C3 C4 . 121.6(3) y C2 C3 Cl1 . 118.8(2) y C4 C3 Cl1 . 119.6(2) y C5 C4 C3 . 118.9(3) y C5 C4 H4 . 120.5 ? C3 C4 H4 . 120.5 ? C4 C5 C6 . 121.0(3) y C4 C5 H5 . 119.5 ? C6 C5 H5 . 119.5 ? C5 C6 C1 . 119.3(3) y C5 C6 H6 . 120.3 ? C1 C6 H6 . 120.3 ? 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 C3 . 1.735(3) y O1 N1 . 1.367(5) y N1 N1 3_666 1.267(5) y N1 C1 . 1.449(4) y C1 C2 . 1.383(4) y C1 C6 . 1.384(5) y C2 C3 . 1.373(4) y C2 H2 . 0.93 ? C3 C4 . 1.381(5) y C4 C5 . 1.368(6) y C4 H4 . 0.93 ? C5 C6 . 1.372(6) y C5 H5 . 0.93 ? C6 H6 . 0.93 ? 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 C2 H2 O1 3_666 0.93 2.08 2.735(6) 126 y C6 H6 O1 1_555 0.93 2.05 2.450(7) 104 y C6 H6 O1 3_776 0.93 2.48 3.271(7) 144 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 C1 C2 3_666 -6.4(5) y O1 N1 C1 C2 . 172.5(3) y N1 N1 C1 C6 3_666 174.1(3) y O1 N1 C1 C6 . -7.0(4) y C6 C1 C2 C3 . -0.3(4) ? N1 C1 C2 C3 . -179.8(2) ? C1 C2 C3 C4 . 0.5(4) ? C1 C2 C3 Cl1 . -179.2(2) ? C2 C3 C4 C5 . -0.4(5) ? Cl1 C3 C4 C5 . 179.3(3) ? C3 C4 C5 C6 . 0.1(5) ? C4 C5 C6 C1 . 0.1(5) ? C2 C1 C6 C5 . 0.0(5) ? N1 C1 C6 C5 . 179.5(3) ?