#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/26/2012611.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_2012611 loop_ _publ_author_name 'Britton, Doyle' 'Mallory, Frank B.' 'Mallory, Clelia W.' _publ_section_title ; The crystal packing of 4,7-dichloro- and 4,7-dibromobenzo[c]furazan 1-oxide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o235 _journal_page_last o238 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H2 Cl2 N2 O2' _chemical_formula_sum 'C6 H2 Cl2 N2 O2' _chemical_formula_weight 205.00 _chemical_name_systematic ; 4,7-dichlorobenzo[c]furazan 1-oxide, polymorph I ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'SHELXTL plus manual additions' _cell_angle_alpha 92.100(10) _cell_angle_beta 109.810(10) _cell_angle_gamma 117.310(10) _cell_formula_units_Z 2 _cell_length_a 7.357(2) _cell_length_b 7.667(2) _cell_length_c 8.190(2) _cell_measurement_reflns_used 2332 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.7 _cell_volume 375.84(18) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction '[SADABS; Sheldrick (1996) and Blessing (1995)]' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w scans' _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 0.021 _diffrn_reflns_av_sigmaI/netI 0.024 _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 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4117 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.72 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 360 _diffrn_standards_number 76 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '[SADABS; Sheldrick (1996) and Blessing (1995)]' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 204 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.40 _refine_diff_density_min -0.34 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 1695 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.09 _refine_ls_R_factor_all 0.040 _refine_ls_R_factor_gt 0.034 _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^)+(0.0591P)^2^+0.0163P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.091 _refine_ls_wR_factor_ref 0.095 _reflns_number_gt 1447 _reflns_number_total 1695 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bk1639.cif _[local]_cod_data_source_block DCL-I _cod_original_cell_volume 375.8(2) _cod_database_code 2012611 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Cl3 0.78094(7) 0.99930(7) 1.20464(5) 0.03031(16) Uani d . 1 . . Cl Cl6 0.35870(8) 0.62810(8) 0.37792(5) 0.03238(17) Uani d . 1 . . Cl O1 0.0421(2) 0.31621(19) 0.54816(17) 0.0342(3) Uani d . 1 . . O O2 0.1670(2) 0.42708(19) 0.85108(16) 0.0291(3) Uani d . 1 . . O N1 0.1871(2) 0.4513(2) 0.68087(18) 0.0239(3) Uani d . 1 . . N N2 0.3423(2) 0.5925(2) 0.98315(18) 0.0254(3) Uani d . 1 . . N C1 0.3702(3) 0.6289(2) 0.7162(2) 0.0194(3) Uani d . 1 . . C C2 0.4622(3) 0.7114(2) 0.9024(2) 0.0193(3) Uani d . 1 . . C C3 0.6620(3) 0.9018(3) 0.9777(2) 0.0215(3) Uani d . 1 . . C C4 0.7545(3) 1.0000(3) 0.8672(3) 0.0266(4) Uani d . 1 . . C H4 0.881(3) 1.132(3) 0.910(3) 0.028(5) Uiso d . 1 . . H C5 0.6581(3) 0.9150(3) 0.6790(2) 0.0265(4) Uani d . 1 . . C H5 0.727(4) 0.983(3) 0.610(3) 0.037(6) Uiso d . 1 . . H C6 0.4705(3) 0.7324(3) 0.6025(2) 0.0226(4) Uani d . 1 . . C 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 Cl3 0.0272(3) 0.0321(3) 0.0221(2) 0.0123(2) 0.00398(18) -0.00301(18) Cl6 0.0452(3) 0.0417(3) 0.0188(2) 0.0263(2) 0.0156(2) 0.0094(2) O1 0.0330(7) 0.0239(7) 0.0235(6) 0.0031(6) 0.0038(5) -0.0036(5) O2 0.0281(7) 0.0229(6) 0.0246(6) 0.0021(5) 0.0129(5) 0.0068(5) N1 0.0252(7) 0.0201(7) 0.0197(7) 0.0068(6) 0.0081(6) 0.0038(6) N2 0.0254(7) 0.0250(8) 0.0197(7) 0.0067(6) 0.0106(6) 0.0050(6) C1 0.0205(8) 0.0183(8) 0.0182(7) 0.0087(7) 0.0081(6) 0.0042(6) C2 0.0202(8) 0.0202(8) 0.0194(8) 0.0104(7) 0.0094(6) 0.0054(6) C3 0.0188(8) 0.0204(8) 0.0213(8) 0.0085(7) 0.0060(6) 0.0026(6) C4 0.0209(8) 0.0214(9) 0.0323(9) 0.0065(7) 0.0106(7) 0.0078(7) C5 0.0267(9) 0.0298(10) 0.0304(9) 0.0141(8) 0.0186(8) 0.0161(8) C6 0.0277(9) 0.0272(9) 0.0206(8) 0.0163(7) 0.0139(7) 0.0101(7) 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 Cl3 C3 . 1.7250(17) ? Cl6 C6 . 1.7214(17) ? O1 N1 . 1.2287(19) ? O2 N2 . 1.3764(19) ? O2 N1 . 1.4604(18) ? N1 C1 . 1.333(2) ? N2 C2 . 1.322(2) ? C1 C2 . 1.421(2) ? C1 C6 . 1.422(2) ? C2 C3 . 1.422(2) ? C3 C4 . 1.359(2) ? C4 C5 . 1.437(3) ? C4 H4 . 0.95(2) ? C5 C6 . 1.354(3) ? C5 H5 . 0.91(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' Cl Cl 0.1484 0.1585 '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 N2 O2 N1 109.32(12) O1 N1 C1 136.55(15) O1 N1 O2 117.61(14) C1 N1 O2 105.83(12) C2 N2 O2 105.49(13) N1 C1 C2 107.03(14) N1 C1 C6 131.03(15) C2 C1 C6 121.94(15) N2 C2 C1 112.33(15) N2 C2 C3 128.64(15) C1 C2 C3 119.03(14) C4 C3 C2 118.37(15) C4 C3 Cl3 122.13(14) C2 C3 Cl3 119.50(12) C3 C4 C5 121.80(17) C3 C4 H4 121.2(12) C5 C4 H4 116.9(12) C6 C5 C4 121.71(16) C6 C5 H5 118.9(14) C4 C5 H5 119.3(14) C5 C6 C1 117.13(15) C5 C6 Cl6 121.67(13) C1 C6 Cl6 121.20(14) 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 N2 O2 N1 O1 -179.67(15) N2 O2 N1 C1 -0.56(17) N1 O2 N2 C2 0.27(17) O1 N1 C1 C2 179.4(2) O2 N1 C1 C2 0.58(17) O1 N1 C1 C6 -0.3(4) O2 N1 C1 C6 -179.11(17) O2 N2 C2 C1 0.10(18) O2 N2 C2 C3 -179.77(16) N1 C1 C2 N2 -0.46(19) C6 C1 C2 N2 179.27(16) N1 C1 C2 C3 179.42(15) C6 C1 C2 C3 -0.8(2) N2 C2 C3 C4 -178.56(18) C1 C2 C3 C4 1.6(2) N2 C2 C3 Cl3 2.2(2) C1 C2 C3 Cl3 -177.65(11) C2 C3 C4 C5 -1.1(3) Cl3 C3 C4 C5 178.10(13) C3 C4 C5 C6 -0.2(3) C4 C5 C6 C1 0.9(3) C4 C5 C6 Cl6 -178.49(13) N1 C1 C6 C5 179.25(17) C2 C1 C6 C5 -0.4(3) N1 C1 C6 Cl6 -1.3(3) C2 C1 C6 Cl6 179.01(12)