#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003327.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_2003327 loop_ _publ_author_name 'Meyers, C. Y.' 'Kolb, V. M.' 'Robinson, P. D.' _publ_section_title ; Dimeric Hydrogen-Bonded Structure of Bis(3-fluorophenylmethine)carbonohydrazide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 775 _journal_page_last 777 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C15 H12 F2 N4 O' _chemical_formula_sum 'C15 H12 F2 N4 O' _chemical_formula_weight 302.28 _chemical_name_systematic ; carbonic dihydrazide, bis(3-fluorophenylmethylene)- ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 100.90(1) _cell_angle_beta 92.99(1) _cell_angle_gamma 86.71(1) _cell_formula_units_Z 2 _cell_length_a 7.805(1) _cell_length_b 15.157(2) _cell_length_c 6.094(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 8.7 _cell_volume 706.12(18) _computing_cell_refinement ' MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN PROCESS (Molecular Structure Corporation, 1985) ; _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'TEXSAN FINISH' _computing_structure_refinement 'TEXSAN LS' _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC5S diffractometer' _diffrn_measurement_method '\w (rate 3\% min^-1^ in \w)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source x-ray_tube _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2684 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.422 _exptl_crystal_description fragment _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.25 _refine_diff_density_min -0.26 _refine_ls_extinction_coef 0.42E-5(7) _refine_ls_extinction_method ; Zachariasen (1967), Type II, Gaussian isotropic ; _refine_ls_goodness_of_fit_obs 1.92 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 1814 _refine_ls_R_factor_obs 0.044 _refine_ls_shift/esd_max 0.0003 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 4F~o~^2^/\s^2^(F~o~^2^)' _refine_ls_wR_factor_obs 0.051 _reflns_number_observed 1814 _reflns_number_total 2483 _reflns_observed_criterion '[I > 1.5\s(I)]' _[local]_cod_data_source_file cr1090.cif _[local]_cod_data_source_block default _cod_original_cell_volume 706.1(4) _cod_database_code 2003327 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C ? International_Tables_Vol_IV_Table_2.3.1 .002 .002 H ? International_Tables_Vol_IV_Table_2.3.1 0 0 O ? International_Tables_Vol_IV_Table_2.3.1 .008 .006 N ? International_Tables_Vol_IV_Table_2.3.1 .004 .003 F ? International_Tables_Vol_IV_Table_2.3.1 .014 .010 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom F1 1.1221(2) 0.3782(1) 1.5520(2) 0.076(1) Uani ? ? F2 0.2851(3) 1.0353(1) 1.2039(3) 0.129(1) Uani ? ? O1 0.4766(2) 0.6133(1) 0.6525(2) 0.054(1) Uani ? ? N1 0.7487(2) 0.4673(1) 0.9088(3) 0.045(1) Uani ? ? N2 0.6492(2) 0.5011(1) 0.7474(3) 0.050(1) Uani ? ? N3 0.6013(2) 0.6301(1) 1.0030(3) 0.047(1) Uani ? ? N4 0.5204(2) 0.7132(1) 1.0697(3) 0.045(1) Uani ? ? C1 0.9207(3) 0.3416(1) 0.9978(4) 0.044(1) Uani ? ? C2 0.9682(3) 0.3838(1) 1.2137(4) 0.047(1) Uani ? ? C3 1.0712(3) 0.3357(2) 1.3424(4) 0.051(1) Uani ? ? C4 1.1270(3) 0.2480(2) 1.2718(4) 0.061(1) Uani ? ? C5 1.0794(3) 0.2071(2) 1.0589(5) 0.067(1) Uani ? ? C6 0.9780(3) 0.2530(1) 0.9211(4) 0.057(1) Uani ? ? C7 0.8133(3) 0.3880(1) 0.8466(4) 0.045(1) Uani ? ? C8 0.5690(3) 0.5841(1) 0.7943(4) 0.043(1) Uani ? ? C9 0.5132(3) 0.7401(1) 1.2791(4) 0.047(1) Uani ? ? C10 0.4243(3) 0.8260(1) 1.3681(4) 0.049(1) Uani ? ? C11 0.4007(3) 0.8934(2) 1.2405(4) 0.060(1) Uani ? ? C12 0.3064(4) 0.9693(2) 1.3262(5) 0.077(1) Uani ? ? C13 0.2330(4) 0.9821(2) 1.5299(6) 0.087(1) Uani ? ? C14 0.2580(4) 0.9162(2) 1.6554(5) 0.084(1) Uani ? ? C15 0.3544(4) 0.8386(2) 1.5769(4) 0.067(1) Uani ? ? H1 0.9303 0.4441 1.2703 0.057 Uiso calc C2 H2 1.1965 0.2166 1.3674 0.073 Uiso calc C4 H3 1.1166 0.1464 1.0055 0.080 Uiso calc C5 H4 0.9471 0.2240 0.7733 0.068 Uiso calc C6 H5 0.788(3) 0.353(1) 0.697(4) 0.054 Uiso ? ? H6 0.621(3) 0.467(2) 0.622(4) 0.059 Uiso ? ? H7 0.649(3) 0.605(1) 1.090(4) 0.056 Uiso ? ? H8 0.551(3) 0.704(1) 1.383(4) 0.055 Uiso ? ? H9 0.4491 0.8866 1.0981 0.072 Uiso calc C11 H10 0.1662 1.0356 1.5828 0.104 Uiso calc C13 H11 0.2086 0.9239 1.7974 0.102 Uiso calc C14 H12 0.3729 0.7936 1.6663 0.081 Uiso calc C15 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 F1 0.078(1) 0.0144(8) -0.0086(7) 0.091(1) 0.0176(8) 0.056(1) F2 0.195(2) 0.045(1) -0.025(1) 0.065(1) 0.026(1) 0.120(2) O1 0.066(1) 0.0102(7) -0.0116(8) 0.0479(9) 0.0196(7) 0.050(1) N1 0.044(1) 0.0036(8) -0.0066(8) 0.044(1) 0.0180(8) 0.049(1) N2 0.059(1) 0.0078(9) -0.012(1) 0.042(1) 0.0135(9) 0.047(1) N3 0.051(1) 0.0098(9) -0.0068(9) 0.042(1) 0.0179(9) 0.050(1) N4 0.045(1) 0.0044(8) -0.0048(9) 0.039(1) 0.0150(8) 0.051(1) C1 0.038(1) 0.001(1) -0.001(1) 0.043(1) 0.018(1) 0.055(1) C2 0.044(1) 0.006(1) 0.002(1) 0.045(1) 0.016(1) 0.054(1) C3 0.045(1) 0.002(1) -0.002(1) 0.063(2) 0.018(1) 0.047(1) C4 0.056(2) 0.008(1) -0.010(1) 0.058(2) 0.032(1) 0.073(2) C5 0.071(2) 0.011(1) -0.013(1) 0.042(1) 0.017(1) 0.086(2) C6 0.058(1) 0.006(1) -0.012(1) 0.044(1) 0.012(1) 0.067(2) C7 0.044(1) 0.002(1) -0.003(1) 0.042(1) 0.014(1) 0.050(1) C8 0.045(1) 0.002(1) -0.002(1) 0.042(1) 0.018(1) 0.046(1) C9 0.049(1) 0.001(1) -0.011(1) 0.046(1) 0.017(1) 0.047(1) C10 0.050(1) 0.001(1) -0.013(1) 0.046(1) 0.007(1) 0.047(1) C11 0.074(2) 0.007(1) -0.012(1) 0.048(1) 0.010(1) 0.055(1) C12 0.095(2) 0.019(1) -0.026(2) 0.050(2) 0.009(1) 0.078(2) C13 0.085(2) 0.027(2) -0.018(2) 0.075(2) -0.019(2) 0.081(2) C14 0.088(2) 0.014(2) -0.002(2) 0.091(2) -0.003(2) 0.065(2) C15 0.076(2) 0.005(1) -0.004(1) 0.068(2) 0.008(1) 0.055(2) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 0 2 0 1 1 1 0 1 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 N2 N1 C7 . 115.0(2) yes N1 N2 C8 . 120.8(2) yes N4 N3 C8 . 119.3(2) yes N3 N4 C9 . 115.8(2) yes C2 C1 C6 . 119.4(2) yes C2 C1 C7 . 122.0(2) yes C6 C1 C7 . 118.6(2) yes C1 C2 C3 . 118.0(2) yes F1 C3 C2 . 117.9(2) yes F1 C3 C4 . 118.5(2) yes C2 C3 C4 . 123.6(2) yes C3 C4 C5 . 117.9(2) yes C4 C5 C6 . 120.8(2) yes C1 C6 C5 . 120.3(2) yes N1 C7 C1 . 122.1(2) yes O1 C8 N2 . 120.9(2) yes O1 C8 N3 . 124.2(2) yes N2 C8 N3 . 114.9(2) yes N4 C9 C10 . 120.3(2) yes C9 C10 C11 . 120.8(2) yes C9 C10 C15 . 119.5(2) yes C11 C10 C15 . 119.6(2) yes C10 C11 C12 . 118.1(2) yes F2 C12 C11 . 118.1(3) yes F2 C12 C13 . 118.7(3) yes C11 C12 C13 . 123.2(3) yes C12 C13 C14 . 118.5(3) yes C13 C14 C15 . 120.4(3) yes C10 C15 C14 . 120.2(3) yes N1 N2 H6 . 121(2) yes C8 N2 H6 . 117(2) yes N4 N3 H7 . 120(2) no C8 N3 H7 . 119(2) no N1 C7 H5 . 122.0(10) no C1 C7 H5 . 116.0(10) no N4 C9 H8 . 122.0(10) no C10 C9 H8 . 117.0(10) no N2 H6 O1 2_666 172(2) yes 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 F1 C3 . 1.367(3) yes F2 C12 . 1.353(3) yes O1 C8 . 1.227(2) yes N1 N2 . 1.377(2) yes N1 C7 . 1.273(3) yes N2 C8 . 1.361(3) yes N3 N4 . 1.375(2) yes N3 C8 . 1.349(3) yes N4 C9 . 1.267(3) yes C1 C2 . 1.391(3) yes C1 C6 . 1.392(3) yes C1 C7 . 1.464(3) yes C2 C3 . 1.369(3) yes C3 C4 . 1.371(3) yes C4 C5 . 1.371(3) yes C5 C6 . 1.380(3) yes C9 C10 . 1.462(3) yes C10 C11 . 1.396(3) yes C10 C15 . 1.387(3) yes C11 C12 . 1.361(3) yes C12 C13 . 1.370(4) yes C13 C14 . 1.369(4) yes C14 C15 . 1.379(4) yes N2 H6 . 0.86(2) yes N3 H7 . 0.78(2) no C7 H5 . 0.98(2) no C9 H8 . 0.94(2) no H6 O1 2_666 2.01(2) yes N2 O1 2_666 2.873(3) yes 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 F1 C3 C2 C1 178.0(2) F1 C3 C4 C5 -178.0(2) F2 C12 C11 C10 179.2(2) F2 C12 C13 C14 -178.5(3) O1 C8 N2 N1 -178.0(2) O1 C8 N2 H6 -9(2) O1 C8 N3 N4 3.6(3) O1 C8 N3 H7 171(2) N1 N2 C8 N3 2.8(3) N1 C7 C1 C2 -4.6(3) N1 C7 C1 C6 176.1(2) N2 N1 C7 C1 -179.3(2) N2 N1 C7 H5 -3.0(10) N2 C8 N3 N4 -177.2(2) N2 C8 N3 H7 -10(2) N3 N4 C9 C10 -177.7(2) N3 N4 C9 H8 -5(2) N3 C8 N2 H6 172(2) N4 C9 C10 C11 -23.2(3) N4 C9 C10 C15 153.2(2) C1 C2 C3 C4 -1.4(4) C1 C6 C5 C4 -0.7(4) C2 C1 C6 C5 0.7(4) C2 C1 C7 H5 179.0(10) C2 C3 C4 C5 1.3(4) C3 C2 C1 C6 0.3(3) C3 C2 C1 C7 -179.0(2) C3 C4 C5 C6 -0.2(4) C5 C6 C1 C7 -180.0(2) C6 C1 C7 H5 .0(10) C7 N1 N2 C8 178.2(2) C7 N1 N2 H6 9(2) C8 N3 N4 C9 159.1(2) C9 N4 N3 H7 -8(2) C9 C10 C11 C12 175.4(2) C9 C10 C15 C14 -174.6(2) C10 C11 C12 C13 -0.5(4) C10 C15 C14 C13 -1.2(5) C11 C10 C9 H8 164(2) C11 C10 C15 C14 1.9(4) C11 C12 C13 C14 1.2(5) C12 C11 C10 C15 -1.1(4) C12 C13 C14 C15 -0.3(5) C15 C10 C9 H8 -19(2) _journal_paper_doi 10.1107/S0108270194011492