#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/84/1508486.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_1508486 loop_ _publ_author_name 'Jasinski, Jerry P.' 'Golen, James A.' 'Samshuddin, Seranthimata' 'Narayana, Badiadka' 'Yathirajan, Hemmige S.' _publ_section_title ; Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide ; _journal_issue 3 _journal_name_full Crystals _journal_page_first 1108 _journal_page_last 1115 _journal_paper_doi 10.3390/cryst2031108 _journal_volume 2 _journal_year 2012 _chemical_formula_moiety 'C16 H13 F2 N3 S' _chemical_formula_sum 'C16 H13 F2 N3 S' _chemical_formula_weight 317.35 _chemical_name_systematic ; 3,5-bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 107.007(18) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.339(2) _cell_length_b 11.1478(17) _cell_length_c 9.541(2) _cell_measurement_reflns_used 2227 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 30.10 _cell_measurement_theta_min 2.97 _cell_volume 1458.4(5) _computing_cell_refinement 'CrysAlisPRO (Oxford Diffraction, 2010)' _computing_data_collection 'CrysAlisPRO (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2010)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 16.1500 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 13239 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.88 _diffrn_reflns_theta_min 2.97 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_T_max 0.9714 _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisRED; Oxford Diffraction, 2010. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.213 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 3483 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0413 _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^)+(0.0479P)^2^+0.3153P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.1047 _reflns_number_gt 2740 _reflns_number_total 3483 _reflns_threshold_expression >2sigma(I) _cod_data_source_file C16H13F2N3S_P21_c_CSD-888534-YBN-27-jpj_crystals-02-01108-s001_DC219.cif _cod_data_source_block ybn-27_chateigner_1508486 _cod_original_cell_volume 1458.5(5) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1508486 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' '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 S1 S 0.51060(3) 0.66711(4) 0.65851(5) 0.04156(14) Uani 1 1 d . F1 F -0.04833(10) 0.16584(14) 0.00948(18) 0.1003(6) Uani 1 1 d . F2 F 0.22012(9) 0.64379(10) 1.08099(12) 0.0582(3) Uani 1 1 d . N1 N 0.39561(12) 0.67846(14) 0.38476(17) 0.0417(3) Uani 1 1 d D H1NB H 0.3459(12) 0.6566(17) 0.3128(19) 0.050 Uiso 1 1 d D H1NA H 0.4305(13) 0.7369(15) 0.375(2) 0.050 Uiso 1 1 d D N2 N 0.35919(9) 0.53126(12) 0.52351(13) 0.0328(3) Uani 1 1 d . N3 N 0.28293(9) 0.49800(12) 0.40180(14) 0.0340(3) Uani 1 1 d . C1 C 0.41703(11) 0.62460(14) 0.51483(17) 0.0308(3) Uani 1 1 d . C2 C 0.37068(11) 0.44932(14) 0.64896(16) 0.0319(3) Uani 1 1 d . H2A H 0.4393 0.4269 0.6911 0.038 Uiso 1 1 calc R C3 C 0.31063(12) 0.34130(14) 0.57149(17) 0.0362(4) Uani 1 1 d . H3B H 0.3525 0.2769 0.5574 0.043 Uiso 1 1 calc R H3C H 0.2682 0.3111 0.6262 0.043 Uiso 1 1 calc R C4 C 0.25286(11) 0.39431(14) 0.42772(17) 0.0329(3) Uani 1 1 d . C5 C 0.17158(11) 0.33484(15) 0.31996(18) 0.0356(4) Uani 1 1 d . C6 C 0.15280(12) 0.21414(17) 0.3322(2) 0.0478(4) Uani 1 1 d . H6A H 0.1908 0.1709 0.4118 0.057 Uiso 1 1 calc R C7 C 0.07852(14) 0.15661(18) 0.2281(3) 0.0611(6) Uani 1 1 d . H7A H 0.0665 0.0753 0.2365 0.073 Uiso 1 1 calc R C8 C 0.02355(13) 0.2219(2) 0.1135(3) 0.0604(6) Uani 1 1 d . C9 C 0.03751(16) 0.3413(2) 0.0981(2) 0.0648(6) Uani 1 1 d . H9A H -0.0025 0.3839 0.0196 0.078 Uiso 1 1 calc R C10 C 0.11232(13) 0.39799(19) 0.2015(2) 0.0521(5) Uani 1 1 d . H10A H 0.1232 0.4794 0.1918 0.063 Uiso 1 1 calc R C11 C 0.33098(10) 0.50465(13) 0.76447(16) 0.0295(3) Uani 1 1 d . C12 C 0.25125(11) 0.58086(15) 0.72676(17) 0.0360(4) Uani 1 1 d . H12A H 0.2229 0.6009 0.6289 0.043 Uiso 1 1 calc R C13 C 0.21317(12) 0.62756(16) 0.83277(19) 0.0407(4) Uani 1 1 d . H13A H 0.1597 0.6788 0.8076 0.049 Uiso 1 1 calc R C14 C 0.25653(12) 0.59614(15) 0.97586(18) 0.0388(4) Uani 1 1 d . C15 C 0.33508(13) 0.52117(16) 1.01848(18) 0.0414(4) Uani 1 1 d . H15A H 0.3628 0.5015 1.1166 0.050 Uiso 1 1 calc R C16 C 0.37207(12) 0.47534(14) 0.91064(17) 0.0361(4) Uani 1 1 d . H16A H 0.4255 0.4240 0.9369 0.043 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 S1 0.0373(2) 0.0438(3) 0.0413(3) -0.00533(18) 0.00787(18) -0.00559(18) F1 0.0615(9) 0.0904(11) 0.1171(13) -0.0320(9) -0.0236(8) -0.0184(7) F2 0.0773(8) 0.0622(7) 0.0429(6) -0.0080(5) 0.0296(6) 0.0094(6) N1 0.0486(9) 0.0400(8) 0.0365(8) 0.0056(6) 0.0125(6) -0.0078(7) N2 0.0359(7) 0.0374(7) 0.0241(6) 0.0016(5) 0.0070(5) -0.0049(5) N3 0.0329(7) 0.0413(8) 0.0268(7) 0.0000(5) 0.0073(5) -0.0024(6) C1 0.0337(7) 0.0297(8) 0.0325(8) -0.0026(6) 0.0150(6) 0.0033(6) C2 0.0327(7) 0.0341(8) 0.0280(8) 0.0033(6) 0.0075(6) 0.0025(6) C3 0.0448(9) 0.0330(8) 0.0309(8) 0.0000(6) 0.0111(7) 0.0005(7) C4 0.0331(7) 0.0370(9) 0.0303(8) -0.0015(6) 0.0117(6) -0.0003(6) C5 0.0308(8) 0.0402(9) 0.0372(9) -0.0040(7) 0.0119(7) -0.0013(7) C6 0.0377(9) 0.0426(10) 0.0588(12) 0.0009(9) 0.0073(8) 0.0012(8) C7 0.0427(10) 0.0420(11) 0.0924(17) -0.0113(11) 0.0103(11) -0.0068(8) C8 0.0348(9) 0.0650(14) 0.0712(14) -0.0212(11) -0.0005(9) -0.0069(9) C9 0.0513(12) 0.0693(15) 0.0583(13) 0.0031(11) -0.0082(10) -0.0034(10) C10 0.0486(10) 0.0491(11) 0.0489(11) 0.0027(9) -0.0011(9) -0.0066(8) C11 0.0308(7) 0.0310(8) 0.0251(7) 0.0006(6) 0.0059(6) -0.0022(6) C12 0.0373(8) 0.0413(9) 0.0269(8) 0.0039(7) 0.0055(6) 0.0056(7) C13 0.0393(8) 0.0420(10) 0.0408(10) 0.0015(7) 0.0116(7) 0.0076(7) C14 0.0484(9) 0.0376(9) 0.0334(9) -0.0058(7) 0.0165(7) -0.0026(7) C15 0.0532(10) 0.0430(10) 0.0245(8) 0.0021(7) 0.0060(7) 0.0001(8) C16 0.0366(8) 0.0366(9) 0.0310(8) 0.0037(7) 0.0034(6) 0.0037(7) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C1 N1 H1NB 121.6(13) C1 N1 H1NA 117.9(14) H1NB N1 H1NA 120.4(19) C1 N2 N3 120.10(12) C1 N2 C2 127.06(13) N3 N2 C2 112.68(12) C4 N3 N2 107.78(13) N1 C1 N2 115.28(14) N1 C1 S1 122.98(13) N2 C1 S1 121.73(12) N2 C2 C11 111.23(13) N2 C2 C3 100.42(12) C11 C2 C3 113.11(12) N2 C2 H2A 110.6 C11 C2 H2A 110.6 C3 C2 H2A 110.6 C4 C3 C2 102.28(13) C4 C3 H3B 111.3 C2 C3 H3B 111.3 C4 C3 H3C 111.3 C2 C3 H3C 111.3 H3B C3 H3C 109.2 N3 C4 C5 120.98(14) N3 C4 C3 113.85(14) C5 C4 C3 125.12(14) C6 C5 C10 118.24(16) C6 C5 C4 120.95(15) C10 C5 C4 120.80(16) C7 C6 C5 121.22(18) C7 C6 H6A 119.4 C5 C6 H6A 119.4 C8 C7 C6 118.26(19) C8 C7 H7A 120.9 C6 C7 H7A 120.9 F1 C8 C7 118.7(2) F1 C8 C9 118.4(2) C7 C8 C9 122.85(18) C8 C9 C10 118.6(2) C8 C9 H9A 120.7 C10 C9 H9A 120.7 C9 C10 C5 120.79(19) C9 C10 H10A 119.6 C5 C10 H10A 119.6 C12 C11 C16 118.82(14) C12 C11 C2 121.27(13) C16 C11 C2 119.85(14) C11 C12 C13 120.87(15) C11 C12 H12A 119.6 C13 C12 H12A 119.6 C14 C13 C12 118.11(15) C14 C13 H13A 120.9 C12 C13 H13A 120.9 F2 C14 C15 118.57(15) F2 C14 C13 118.21(15) C15 C14 C13 123.21(16) C14 C15 C16 117.78(15) C14 C15 H15A 121.1 C16 C15 H15A 121.1 C15 C16 C11 121.21(15) C15 C16 H16A 119.4 C11 C16 H16A 119.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.6818(16) F1 C8 1.356(2) F2 C14 1.3665(19) N1 C1 1.331(2) N1 H1NB 0.868(15) N1 H1NA 0.843(15) N2 C1 1.3482(19) N2 N3 1.3924(17) N2 C2 1.4761(19) N3 C4 1.283(2) C2 C11 1.512(2) C2 C3 1.538(2) C2 H2A 0.9800 C3 C4 1.501(2) C3 H3B 0.9700 C3 H3C 0.9700 C4 C5 1.468(2) C5 C6 1.384(2) C5 C10 1.391(2) C6 C7 1.383(3) C6 H6A 0.9300 C7 C8 1.358(3) C7 H7A 0.9300 C8 C9 1.361(3) C9 C10 1.380(3) C9 H9A 0.9300 C10 H10A 0.9300 C11 C12 1.385(2) C11 C16 1.385(2) C12 C13 1.384(2) C12 H12A 0.9300 C13 C14 1.370(2) C13 H13A 0.9300 C14 C15 1.366(2) C15 C16 1.386(2) C15 H15A 0.9300 C16 H16A 0.9300 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 H1NB F2 0.868(15) 2.414(15) 3.258(2) 164.2(17) 1_554 N1 H1NA S1 0.843(15) 2.850(17) 3.5249(16) 138.4(17) 4_575 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 C1 N2 N3 C4 166.66(13) C2 N2 N3 C4 -9.05(17) N3 N2 C1 N1 -0.5(2) C2 N2 C1 N1 174.56(14) N3 N2 C1 S1 -179.41(10) C2 N2 C1 S1 -4.4(2) C1 N2 C2 C11 80.82(18) N3 N2 C2 C11 -103.83(14) C1 N2 C2 C3 -159.22(15) N3 N2 C2 C3 16.13(16) N2 C2 C3 C4 -15.92(14) C11 C2 C3 C4 102.69(14) N2 N3 C4 C5 179.36(13) N2 N3 C4 C3 -3.03(18) C2 C3 C4 N3 12.85(18) C2 C3 C4 C5 -169.65(14) N3 C4 C5 C6 165.65(16) C3 C4 C5 C6 -11.7(2) N3 C4 C5 C10 -13.3(2) C3 C4 C5 C10 169.35(16) C10 C5 C6 C7 1.3(3) C4 C5 C6 C7 -177.64(17) C5 C6 C7 C8 -0.5(3) C6 C7 C8 F1 178.82(19) C6 C7 C8 C9 -1.1(4) F1 C8 C9 C10 -178.2(2) C7 C8 C9 C10 1.7(4) C8 C9 C10 C5 -0.8(3) C6 C5 C10 C9 -0.7(3) C4 C5 C10 C9 178.29(18) N2 C2 C11 C12 33.26(19) C3 C2 C11 C12 -78.87(18) N2 C2 C11 C16 -149.41(14) C3 C2 C11 C16 98.46(16) C16 C11 C12 C13 0.2(2) C2 C11 C12 C13 177.58(15) C11 C12 C13 C14 -0.1(3) C12 C13 C14 F2 178.88(15) C12 C13 C14 C15 -0.1(3) F2 C14 C15 C16 -178.91(15) C13 C14 C15 C16 0.1(3) C14 C15 C16 C11 0.1(2) C12 C11 C16 C15 -0.3(2) C2 C11 C16 C15 -177.65(15)