#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151806.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_7151806 loop_ _publ_author_name 'Yella, Ramesh' 'Khatun, Nilufa' 'Rout, Saroj Kumar' 'Patel, Bhisma K.' _publ_section_title ; Tandem regioselective synthesis of tetrazoles and related heterocycles using iodine. ; _journal_issue 9 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3235 _journal_page_last 3245 _journal_volume 9 _journal_year 2011 _chemical_formula_moiety 'C13 H9 Cl2 N5' _chemical_formula_sum 'C13 H9 Cl2 N5' _chemical_formula_weight 306.15 _chemical_name_systematic ; ? ; _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 SHELXL-97 _cell_angle_alpha 81.772(2) _cell_angle_beta 70.996(2) _cell_angle_gamma 76.860(2) _cell_formula_units_Z 2 _cell_length_a 7.3229(2) _cell_length_b 9.8303(3) _cell_length_c 10.1610(3) _cell_measurement_reflns_used 5469 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.26 _cell_measurement_theta_min 2.90 _cell_volume 671.58(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega 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 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9197 _diffrn_reflns_theta_full 28.31 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 2.13 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_meas 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.387 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef 0.050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 3280 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0406 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.1167P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1172 _refine_ls_wR_factor_ref 0.1242 _reflns_number_gt 2756 _reflns_number_total 3341 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0ob01007c.txt _[local]_cod_data_source_block 7b _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7151806 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.12069(8) 0.54198(5) 0.27397(6) 0.06821(19) Uani 1 1 d . . . Cl2 Cl 0.33696(7) 1.13966(6) 0.29135(6) 0.06812(19) Uani 1 1 d . . . N1 N 0.98776(17) 0.81415(12) 0.12742(14) 0.0417(3) Uani 1 1 d . . . N5 N 0.7384(2) 0.97929(14) 0.26915(15) 0.0470(3) Uani 1 1 d . . . N2 N 1.18322(19) 0.80500(15) 0.05335(16) 0.0534(4) Uani 1 1 d . . . N4 N 1.0765(2) 0.99979(14) 0.16024(16) 0.0511(3) Uani 1 1 d . . . N3 N 1.2319(2) 0.91522(16) 0.07557(18) 0.0570(4) Uani 1 1 d . . . C6 C 0.8853(2) 0.70545(14) 0.13092(15) 0.0382(3) Uani 1 1 d . . . C1 C 0.9393(2) 0.57330(15) 0.19316(16) 0.0425(3) Uani 1 1 d . . . C8 C 0.6782(2) 1.09175(14) 0.35509(15) 0.0415(3) Uani 1 1 d . . . C5 C 0.7340(2) 0.73168(16) 0.07234(17) 0.0466(4) Uani 1 1 d . . . H5 H 0.6975 0.8202 0.0314 0.056 Uiso 1 1 calc R . . C7 C 0.9269(2) 0.93532(14) 0.19026(16) 0.0401(3) Uani 1 1 d . . . C9 C 0.4901(2) 1.17284(16) 0.37719(16) 0.0462(4) Uani 1 1 d . . . C3 C 0.6948(3) 0.49314(18) 0.13297(19) 0.0546(4) Uani 1 1 d . . . H3 H 0.6311 0.4215 0.1324 0.066 Uiso 1 1 calc R . . C4 C 0.6368(2) 0.62500(19) 0.07503(19) 0.0533(4) Uani 1 1 d . . . H4 H 0.5327 0.6424 0.0378 0.064 Uiso 1 1 calc R . . C2 C 0.8456(3) 0.46602(16) 0.19157(18) 0.0514(4) Uani 1 1 d . . . H2 H 0.8843 0.3766 0.2298 0.062 Uiso 1 1 calc R . . C10 C 0.4225(3) 1.27904(19) 0.4678(2) 0.0619(5) Uani 1 1 d . . . H10 H 0.2961 1.3322 0.4822 0.074 Uiso 1 1 calc R . . C13 C 0.7987(3) 1.11988(19) 0.4244(2) 0.0570(4) Uani 1 1 d . . . H13 H 0.9252 1.0670 0.4106 0.068 Uiso 1 1 calc R . . C12 C 0.7313(4) 1.2264(2) 0.5142(2) 0.0688(5) Uani 1 1 d . . . H12 H 0.8130 1.2449 0.5601 0.083 Uiso 1 1 calc R . . C11 C 0.5437(4) 1.3052(2) 0.5360(2) 0.0710(6) Uani 1 1 d . . . H11 H 0.4991 1.3761 0.5969 0.085 Uiso 1 1 calc R . . H1N H 0.651(3) 0.946(2) 0.263(2) 0.058(6) 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 Cl1 0.0776(3) 0.0592(3) 0.0784(4) -0.0017(2) -0.0468(3) -0.0021(2) Cl2 0.0509(3) 0.0774(3) 0.0768(3) -0.0163(3) -0.0231(2) -0.0019(2) N1 0.0382(6) 0.0349(6) 0.0521(7) -0.0109(5) -0.0124(5) -0.0046(5) N5 0.0439(7) 0.0389(6) 0.0602(8) -0.0188(6) -0.0126(6) -0.0075(5) N2 0.0398(7) 0.0504(7) 0.0683(9) -0.0147(7) -0.0113(6) -0.0065(5) N4 0.0497(7) 0.0439(7) 0.0633(9) -0.0097(6) -0.0166(6) -0.0133(6) N3 0.0459(7) 0.0539(8) 0.0717(10) -0.0132(7) -0.0122(7) -0.0140(6) C6 0.0391(7) 0.0326(6) 0.0422(7) -0.0120(5) -0.0093(5) -0.0042(5) C1 0.0454(8) 0.0366(7) 0.0436(8) -0.0105(6) -0.0121(6) -0.0017(6) C8 0.0505(8) 0.0313(6) 0.0415(7) -0.0055(5) -0.0115(6) -0.0078(6) C5 0.0461(8) 0.0396(7) 0.0551(9) -0.0103(6) -0.0178(7) -0.0027(6) C7 0.0446(7) 0.0314(6) 0.0473(8) -0.0058(6) -0.0183(6) -0.0052(5) C9 0.0510(8) 0.0398(7) 0.0432(8) -0.0040(6) -0.0089(6) -0.0069(6) C3 0.0573(9) 0.0493(9) 0.0589(10) -0.0219(8) -0.0061(8) -0.0195(7) C4 0.0471(9) 0.0581(10) 0.0611(10) -0.0208(8) -0.0188(7) -0.0095(7) C2 0.0641(10) 0.0337(7) 0.0512(9) -0.0104(6) -0.0084(7) -0.0078(6) C10 0.0700(11) 0.0454(9) 0.0536(10) -0.0115(8) -0.0022(8) 0.0023(8) C13 0.0680(11) 0.0514(9) 0.0578(10) -0.0132(8) -0.0259(8) -0.0080(8) C12 0.0951(15) 0.0660(12) 0.0552(10) -0.0186(9) -0.0259(10) -0.0221(11) C11 0.1049(16) 0.0512(10) 0.0493(10) -0.0211(8) -0.0052(10) -0.0160(10) 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 N2 107.59(12) . . ? C7 N1 C6 130.99(12) . . ? N2 N1 C6 121.40(11) . . ? C7 N5 C8 124.01(13) . . ? N3 N2 N1 106.02(12) . . ? C7 N4 N3 105.39(12) . . ? N2 N3 N4 111.86(13) . . ? C5 C6 C1 120.31(13) . . ? C5 C6 N1 119.95(13) . . ? C1 C6 N1 119.74(13) . . ? C2 C1 C6 119.85(15) . . ? C2 C1 Cl1 119.61(12) . . ? C6 C1 Cl1 120.55(11) . . ? C13 C8 C9 118.69(14) . . ? C13 C8 N5 121.55(15) . . ? C9 C8 N5 119.68(14) . . ? C6 C5 C4 119.50(15) . . ? N4 C7 N1 109.12(13) . . ? N4 C7 N5 127.83(13) . . ? N1 C7 N5 123.04(13) . . ? C10 C9 C8 120.98(16) . . ? C10 C9 Cl2 119.55(14) . . ? C8 C9 Cl2 119.47(11) . . ? C2 C3 C4 120.91(14) . . ? C3 C4 C5 119.97(16) . . ? C3 C2 C1 119.41(15) . . ? C11 C10 C9 119.55(18) . . ? C12 C13 C8 120.20(18) . . ? C11 C12 C13 120.47(19) . . ? C10 C11 C12 120.11(16) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7281(16) . ? Cl2 C9 1.7347(18) . ? N1 C7 1.3476(17) . ? N1 N2 1.3720(17) . ? N1 C6 1.4290(17) . ? N5 C7 1.357(2) . ? N5 C8 1.4082(18) . ? N2 N3 1.2846(19) . ? N4 C7 1.3183(19) . ? N4 N3 1.365(2) . ? C6 C5 1.380(2) . ? C6 C1 1.392(2) . ? C1 C2 1.387(2) . ? C8 C13 1.387(2) . ? C8 C9 1.391(2) . ? C5 C4 1.388(2) . ? C9 C10 1.388(2) . ? C3 C2 1.376(3) . ? C3 C4 1.379(3) . ? C10 C11 1.374(3) . ? C13 C12 1.384(2) . ? C12 C11 1.380(3) . ? _journal_paper_doi 10.1039/c0ob01007c