#------------------------------------------------------------------------------ #$Date: 2016-03-26 13:55:45 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180240 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/26/7112622.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_7112622 loop_ _publ_author_name 'Zhenxing Liu' 'Long Wang' 'Haocheng Tan' 'Shiyi Zhou' 'Tianren Fu' 'Ying Xia' 'Yan Zhang' 'Jianbo Wang' _publ_section_title ; Synthesis of 1H-indazoles from N-tosylhydrazones and nitroaromatic compounds ; _journal_name_full Chem.Commun. _journal_page_first 5061 _journal_paper_doi 10.1039/C4CC00962B _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C14 H11 N3 O2' _chemical_formula_sum 'C14 H11 N3 O2' _chemical_formula_weight 253.26 _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2012-11-23 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 12.2236(12) _cell_length_b 9.7043(5) _cell_length_c 19.5840(11) _cell_measurement_reflns_used 2806 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 29.2919 _cell_measurement_theta_min 3.3864 _cell_volume 2323.1(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'J. Appl. Cryst. (2007) 40, 786-790' _diffrn_ambient_temperature 100.01(10) _diffrn_detector_area_resol_mean 10.3914 _diffrn_measured_fraction_theta_full 0.9868 _diffrn_measured_fraction_theta_max 0.8971 _diffrn_measurement_details ; 1 omega -21.00 88.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 11.7128 77.0000 -30.0000 109 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0575846000 _diffrn_orient_matrix_UB_12 0.0052336000 _diffrn_orient_matrix_UB_13 0.0042653000 _diffrn_orient_matrix_UB_21 0.0073004000 _diffrn_orient_matrix_UB_22 0.0089360000 _diffrn_orient_matrix_UB_23 0.0356029000 _diffrn_orient_matrix_UB_31 0.0033220000 _diffrn_orient_matrix_UB_32 0.0722993000 _diffrn_orient_matrix_UB_33 -0.0047777000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_unetI/netI 0.0274 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5437 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 3.39 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.216 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 177 _refine_ls_number_reflns 2267 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0392 _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^)+(0.0519P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.0996 _reflns_number_gt 1987 _reflns_number_total 2267 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c4cc00962b2.cif _cod_data_source_block liuzhenxing _cod_database_code 7112622 #BEGIN Tags that were not found in dictionaries: _chemical_oxdiff_formula C14H11N3O2 _reflns_odcompleteness_completeness 98.68 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 #END Tags that were not found in dictionaries loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.74663(10) 0.45800(13) 0.57639(6) 0.0152(3) Uani 1 1 d . C2 C 0.68513(10) 0.36578(13) 0.53731(7) 0.0166(3) Uani 1 1 d . H2 H 0.7170 0.3051 0.5064 0.020 Uiso 1 1 calc R C3 C 0.57400(11) 0.37130(13) 0.54792(6) 0.0167(3) Uani 1 1 d . C4 C 0.52243(11) 0.46172(14) 0.59318(7) 0.0187(3) Uani 1 1 d . H4 H 0.4467 0.4610 0.5976 0.022 Uiso 1 1 calc R C5 C 0.58439(10) 0.55135(14) 0.63091(7) 0.0175(3) Uani 1 1 d . H5 H 0.5512 0.6116 0.6615 0.021 Uiso 1 1 calc R C6 C 0.69937(10) 0.55133(13) 0.62293(7) 0.0146(3) Uani 1 1 d . C7 C 0.79125(10) 0.61971(13) 0.65338(7) 0.0148(3) Uani 1 1 d . C8 C 0.79472(10) 0.72509(13) 0.70703(7) 0.0149(3) Uani 1 1 d . C9 C 0.70066(10) 0.79585(14) 0.72682(7) 0.0174(3) Uani 1 1 d . H9 H 0.6345 0.7764 0.7054 0.021 Uiso 1 1 calc R C10 C 0.70401(10) 0.89429(14) 0.77766(7) 0.0183(3) Uani 1 1 d . H10 H 0.6400 0.9401 0.7897 0.022 Uiso 1 1 calc R C11 C 0.80085(10) 0.92640(14) 0.81119(7) 0.0180(3) Uani 1 1 d . C12 C 0.89527(11) 0.85641(15) 0.79075(7) 0.0219(3) Uani 1 1 d . H12 H 0.9615 0.8768 0.8119 0.026 Uiso 1 1 calc R C13 C 0.89275(11) 0.75784(14) 0.74007(7) 0.0200(3) Uani 1 1 d . H13 H 0.9569 0.7127 0.7277 0.024 Uiso 1 1 calc R C14 C 0.80432(12) 1.03192(15) 0.86721(8) 0.0243(3) Uani 1 1 d . H14A H 0.7520 1.1033 0.8578 0.036 Uiso 1 1 calc R H14B H 0.8763 1.0712 0.8697 0.036 Uiso 1 1 calc R H14C H 0.7868 0.9888 0.9100 0.036 Uiso 1 1 calc R N1 N 0.88455(9) 0.57198(11) 0.62712(6) 0.0171(3) Uani 1 1 d . N2 N 0.85675(9) 0.47487(12) 0.58075(6) 0.0175(3) Uani 1 1 d . N3 N 0.50497(9) 0.27297(12) 0.51130(6) 0.0198(3) Uani 1 1 d . O1 O 0.54844(8) 0.19239(10) 0.47111(5) 0.0268(3) Uani 1 1 d . O2 O 0.40597(8) 0.27382(11) 0.52221(5) 0.0274(3) Uani 1 1 d . H2A H 0.9103(14) 0.4279(18) 0.5591(9) 0.027(4) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0140(6) 0.0160(6) 0.0157(6) 0.0028(5) 0.0004(5) 0.0007(5) C2 0.0185(7) 0.0163(6) 0.0151(6) 0.0003(5) -0.0003(5) 0.0011(5) C3 0.0186(7) 0.0166(7) 0.0147(6) 0.0018(5) -0.0033(5) -0.0032(5) C4 0.0134(6) 0.0232(7) 0.0194(7) 0.0015(6) 0.0001(5) -0.0013(5) C5 0.0156(6) 0.0203(7) 0.0165(7) -0.0011(5) 0.0013(5) 0.0011(5) C6 0.0166(7) 0.0137(6) 0.0136(6) 0.0017(5) -0.0010(5) 0.0009(5) C7 0.0142(6) 0.0143(6) 0.0159(6) 0.0024(5) 0.0000(5) 0.0015(5) C8 0.0169(7) 0.0134(6) 0.0144(6) 0.0024(5) 0.0003(5) -0.0009(5) C9 0.0138(7) 0.0185(7) 0.0199(7) -0.0001(6) -0.0010(5) -0.0003(5) C10 0.0165(7) 0.0174(7) 0.0210(7) -0.0010(6) 0.0025(5) 0.0021(5) C11 0.0204(7) 0.0166(7) 0.0169(7) 0.0005(5) 0.0003(5) -0.0001(5) C12 0.0168(7) 0.0242(7) 0.0249(7) -0.0054(6) -0.0056(5) 0.0013(6) C13 0.0140(6) 0.0223(7) 0.0236(7) -0.0035(6) -0.0016(5) 0.0032(5) C14 0.0250(8) 0.0247(8) 0.0232(7) -0.0073(6) -0.0018(6) 0.0019(6) N1 0.0163(5) 0.0166(6) 0.0185(6) -0.0027(5) 0.0007(4) 0.0002(5) N2 0.0149(6) 0.0177(6) 0.0199(6) -0.0052(5) 0.0010(5) 0.0006(5) N3 0.0200(6) 0.0205(6) 0.0189(6) 0.0012(5) -0.0031(5) -0.0032(5) O1 0.0272(6) 0.0249(6) 0.0282(6) -0.0105(5) -0.0040(4) -0.0002(4) O2 0.0175(5) 0.0338(6) 0.0308(6) -0.0047(5) -0.0007(4) -0.0087(4) 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 C2 C1 C6 123.07(12) N2 C1 C2 130.14(12) N2 C1 C6 106.75(11) C1 C2 H2 122.5 C3 C2 C1 115.07(12) C3 C2 H2 122.5 C2 C3 C4 124.46(12) C2 C3 N3 118.07(12) C4 C3 N3 117.43(12) C3 C4 H4 120.3 C5 C4 C3 119.43(12) C5 C4 H4 120.3 C4 C5 H5 120.3 C4 C5 C6 119.33(12) C6 C5 H5 120.3 C1 C6 C5 118.63(12) C1 C6 C7 104.20(11) C5 C6 C7 137.07(12) C6 C7 C8 130.02(11) N1 C7 C6 110.40(11) N1 C7 C8 119.57(11) C9 C8 C7 121.23(11) C9 C8 C13 117.79(12) C13 C8 C7 120.98(11) C8 C9 H9 119.4 C10 C9 C8 121.12(12) C10 C9 H9 119.4 C9 C10 H10 119.3 C9 C10 C11 121.43(12) C11 C10 H10 119.3 C10 C11 C12 117.34(13) C10 C11 C14 121.50(12) C12 C11 C14 121.16(12) C11 C12 H12 119.2 C13 C12 C11 121.66(13) C13 C12 H12 119.2 C8 C13 H13 119.7 C12 C13 C8 120.65(12) C12 C13 H13 119.7 C11 C14 H14A 109.5 C11 C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C7 N1 N2 106.62(10) C1 N2 H2A 128.9(11) N1 N2 C1 112.03(11) N1 N2 H2A 119.0(11) O1 N3 C3 118.66(11) O2 N3 C3 118.60(11) O2 N3 O1 122.74(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.3970(19) C1 C6 1.4088(18) C1 N2 1.3587(17) C2 H2 0.9300 C2 C3 1.3752(18) C3 C4 1.3976(19) C3 N3 1.4619(17) C4 H4 0.9300 C4 C5 1.3697(19) C5 H5 0.9300 C5 C6 1.4142(17) C6 C7 1.4343(17) C7 C8 1.4669(19) C7 N1 1.3340(16) C8 C9 1.3942(18) C8 C13 1.3984(18) C9 H9 0.9300 C9 C10 1.380(2) C10 H10 0.9300 C10 C11 1.3891(18) C11 C12 1.3977(19) C11 C14 1.5013(19) C12 H12 0.9300 C12 C13 1.379(2) C13 H13 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 N1 N2 1.3522(16) N2 H2A 0.904(18) N3 O1 1.2301(15) N3 O2 1.2289(15)