#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/58/7205806.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_7205806 loop_ _publ_author_name 'Singh, Udai P.' 'Kashyap, Sujata' 'Singh, Hari Ji' 'Butcher, Ray J.' _publ_section_title ; Anion directed supramolecular architecture of pyrazole based ionic salts ; _journal_issue 12 _journal_name_full CrystEngComm _journal_page_first 4110 _journal_paper_doi 10.1039/c0ce00820f _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C15 H13 N2, Cl' _chemical_formula_sum 'C15 H13 Cl N2' _chemical_formula_weight 256.72 _chemical_name_systematic ; ? ; _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 99.5070(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1846(2) _cell_length_b 17.0013(4) _cell_length_c 9.4108(2) _cell_measurement_reflns_used 125 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 28.33 _cell_measurement_theta_min 2.40 _cell_volume 1291.52(5) _computing_cell_refinement 'Bruker XSCANS' _computing_data_collection 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker Apex 2 CCD Diffractometer' _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 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 22140 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 2.40 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_T_max 0.930 _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.190 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 3177 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0363 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.2578P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.0986 _reflns_number_gt 2570 _reflns_number_total 3177 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ce00820f.txt _cod_data_source_block ups849 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7205806 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_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 0.27946(4) 0.44092(2) -0.03891(4) 0.04748(13) Uani 1 1 d . . . N1 N 0.54340(13) 0.37931(6) 0.20073(11) 0.0377(3) Uani 1 1 d . . . H1A H 0.4571 0.3947 0.1385 0.045 Uiso 1 1 calc R . . N2 N 0.69179(13) 0.41582(7) 0.22530(11) 0.0386(3) Uani 1 1 d . . . H2B H 0.7175 0.4586 0.1813 0.046 Uiso 1 1 calc R . . C1 C 0.54802(15) 0.31588(8) 0.28583(13) 0.0350(3) Uani 1 1 d . . . C2 C 0.70573(16) 0.31305(8) 0.36673(14) 0.0410(3) Uani 1 1 d . . . H2A H 0.7459 0.2744 0.4367 0.049 Uiso 1 1 calc R . . C3 C 0.79410(16) 0.37651(8) 0.32752(13) 0.0366(3) Uani 1 1 d . . . C4 C 0.96497(16) 0.40064(8) 0.38292(13) 0.0380(3) Uani 1 1 d . . . C5 C 1.05022(18) 0.45509(9) 0.31449(16) 0.0483(4) Uani 1 1 d . . . H5A H 0.9972 0.4801 0.2289 0.058 Uiso 1 1 calc R . . C6 C 1.2131(2) 0.47319(10) 0.37082(19) 0.0571(4) Uani 1 1 d . . . H6A H 1.2717 0.5105 0.3233 0.068 Uiso 1 1 calc R . . C7 C 1.29084(19) 0.43743(10) 0.49552(19) 0.0558(4) Uani 1 1 d . . . H7A H 1.4027 0.4499 0.5334 0.067 Uiso 1 1 calc R . . C8 C 1.20639(19) 0.38389(11) 0.56447(16) 0.0575(4) Uani 1 1 d . . . H8A H 1.2593 0.3596 0.6509 0.069 Uiso 1 1 calc R . . C9 C 1.04516(18) 0.36525(10) 0.50878(15) 0.0509(4) Uani 1 1 d . . . H9A H 0.9877 0.3277 0.5568 0.061 Uiso 1 1 calc R . . C10 C 0.40633(16) 0.26363(8) 0.28965(13) 0.0352(3) Uani 1 1 d . . . C11 C 0.24700(16) 0.28272(9) 0.22320(14) 0.0412(3) Uani 1 1 d . . . H11A H 0.2275 0.3303 0.1703 0.049 Uiso 1 1 calc R . . C12 C 0.11648(19) 0.23249(10) 0.23396(17) 0.0514(4) Uani 1 1 d . . . H12A H 0.0078 0.2456 0.1876 0.062 Uiso 1 1 calc R . . C13 C 0.1432(2) 0.16359(10) 0.31161(18) 0.0558(4) Uani 1 1 d . . . H13A H 0.0529 0.1299 0.3205 0.067 Uiso 1 1 calc R . . C14 C 0.3014(2) 0.14379(10) 0.37624(17) 0.0565(4) Uani 1 1 d . . . H14A H 0.3200 0.0959 0.4284 0.068 Uiso 1 1 calc R . . C15 C 0.43296(19) 0.19303(8) 0.36581(15) 0.0463(3) Uani 1 1 d . . . H15A H 0.5417 0.1789 0.4104 0.056 Uiso 1 1 calc R . . 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 0.0422(2) 0.0468(2) 0.0477(2) 0.01587(15) -0.00960(14) -0.00613(14) N1 0.0344(5) 0.0395(6) 0.0363(5) 0.0077(5) -0.0027(4) 0.0011(5) N2 0.0368(6) 0.0390(6) 0.0377(5) 0.0092(5) -0.0010(4) -0.0025(5) C1 0.0368(6) 0.0357(7) 0.0321(6) 0.0027(5) 0.0044(5) 0.0039(5) C2 0.0373(7) 0.0447(8) 0.0392(6) 0.0126(6) 0.0008(5) 0.0044(6) C3 0.0351(6) 0.0424(8) 0.0315(6) 0.0055(5) 0.0031(5) 0.0047(5) C4 0.0350(6) 0.0427(8) 0.0354(6) 0.0011(5) 0.0029(5) 0.0035(6) C5 0.0428(8) 0.0475(8) 0.0517(8) 0.0100(6) -0.0007(6) -0.0009(6) C6 0.0449(8) 0.0533(10) 0.0710(10) 0.0077(8) 0.0037(7) -0.0084(7) C7 0.0378(8) 0.0628(11) 0.0627(9) -0.0067(8) -0.0040(7) -0.0031(7) C8 0.0458(8) 0.0771(12) 0.0441(8) 0.0050(8) -0.0086(6) 0.0026(8) C9 0.0425(8) 0.0687(10) 0.0394(7) 0.0123(7) 0.0009(6) -0.0020(7) C10 0.0380(6) 0.0346(7) 0.0328(6) -0.0008(5) 0.0053(5) 0.0007(5) C11 0.0398(7) 0.0398(7) 0.0432(7) 0.0007(6) 0.0045(5) 0.0025(6) C12 0.0414(8) 0.0540(9) 0.0583(9) -0.0045(7) 0.0070(6) -0.0053(7) C13 0.0586(10) 0.0522(10) 0.0582(9) -0.0038(7) 0.0145(7) -0.0192(8) C14 0.0737(11) 0.0411(8) 0.0530(8) 0.0071(7) 0.0060(8) -0.0101(8) C15 0.0509(8) 0.0395(8) 0.0462(7) 0.0053(6) 0.0010(6) 0.0008(6) 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 C1 N1 N2 109.39(10) . . ? C1 N1 H1A 125.3 . . ? N2 N1 H1A 125.3 . . ? C3 N2 N1 109.31(11) . . ? C3 N2 H2B 125.3 . . ? N1 N2 H2B 125.3 . . ? N1 C1 C2 106.72(11) . . ? N1 C1 C10 123.91(11) . . ? C2 C1 C10 129.34(12) . . ? C3 C2 C1 107.88(11) . . ? C3 C2 H2A 126.1 . . ? C1 C2 H2A 126.1 . . ? N2 C3 C2 106.70(11) . . ? N2 C3 C4 124.02(12) . . ? C2 C3 C4 129.27(11) . . ? C5 C4 C9 118.87(13) . . ? C5 C4 C3 123.14(12) . . ? C9 C4 C3 117.96(12) . . ? C4 C5 C6 119.92(14) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 120.45(15) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C8 C7 C6 119.85(14) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C7 C8 C9 120.05(14) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C8 C9 C4 120.85(14) . . ? C8 C9 H9A 119.6 . . ? C4 C9 H9A 119.6 . . ? C11 C10 C15 119.18(13) . . ? C11 C10 C1 122.36(12) . . ? C15 C10 C1 118.45(12) . . ? C12 C11 C10 120.10(13) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C13 C12 C11 120.40(14) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 119.79(14) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C15 120.49(15) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 C10 120.02(14) . . ? C14 C15 H15A 120.0 . . ? C10 C15 H15A 120.0 . . ? 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 N1 C1 1.3401(16) . ? N1 N2 1.3494(15) . ? N1 H1A 0.8800 . ? N2 C3 1.3443(16) . ? N2 H2B 0.8800 . ? C1 C2 1.3869(18) . ? C1 C10 1.4659(18) . ? C2 C3 1.3825(19) . ? C2 H2A 0.9500 . ? C3 C4 1.4680(18) . ? C4 C5 1.381(2) . ? C4 C9 1.3924(18) . ? C5 C6 1.385(2) . ? C5 H5A 0.9500 . ? C6 C7 1.380(2) . ? C6 H6A 0.9500 . ? C7 C8 1.369(2) . ? C7 H7A 0.9500 . ? C8 C9 1.374(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.3884(18) . ? C10 C15 1.3964(19) . ? C11 C12 1.384(2) . ? C11 H11A 0.9500 . ? C12 C13 1.379(2) . ? C12 H12A 0.9500 . ? C13 C14 1.378(2) . ? C13 H13A 0.9500 . ? C14 C15 1.380(2) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.88 2.17 3.0398(10) 168.9 . N2 H2B Cl1 0.88 2.17 3.0333(12) 165.5 3_665 C11 H11A Cl1 0.95 2.80 3.6886(15) 155.1 . C15 H15A Cl1 0.95 2.80 3.6322(15) 146.3 4_666 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C3 -0.34(15) . . . . ? N2 N1 C1 C2 0.12(14) . . . . ? N2 N1 C1 C10 178.44(11) . . . . ? N1 C1 C2 C3 0.13(15) . . . . ? C10 C1 C2 C3 -178.06(13) . . . . ? N1 N2 C3 C2 0.41(15) . . . . ? N1 N2 C3 C4 -178.84(11) . . . . ? C1 C2 C3 N2 -0.33(16) . . . . ? C1 C2 C3 C4 178.86(13) . . . . ? N2 C3 C4 C5 -15.1(2) . . . . ? C2 C3 C4 C5 165.80(15) . . . . ? N2 C3 C4 C9 166.40(14) . . . . ? C2 C3 C4 C9 -12.7(2) . . . . ? C9 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C6 -178.00(14) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C9 0.7(3) . . . . ? C7 C8 C9 C4 -0.5(3) . . . . ? C5 C4 C9 C8 0.0(2) . . . . ? C3 C4 C9 C8 178.50(15) . . . . ? N1 C1 C10 C11 -11.2(2) . . . . ? C2 C1 C10 C11 166.72(14) . . . . ? N1 C1 C10 C15 170.28(13) . . . . ? C2 C1 C10 C15 -11.8(2) . . . . ? C15 C10 C11 C12 0.6(2) . . . . ? C1 C10 C11 C12 -177.89(13) . . . . ? C10 C11 C12 C13 0.6(2) . . . . ? C11 C12 C13 C14 -1.4(2) . . . . ? C12 C13 C14 C15 1.1(2) . . . . ? C13 C14 C15 C10 0.2(2) . . . . ? C11 C10 C15 C14 -1.0(2) . . . . ? C1 C10 C15 C14 177.58(13) . . . . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30653764