#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206812.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_2206812 loop_ _publ_author_name 'Zhong, Ping' 'Yang, Zhiping' 'Shi, Qian' 'Hu, Maolin' 'Li, Shuyan' 'Tang, Riyuan' _publ_section_title 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-1H-pyrazole-3-carbonitrile _journal_coeditor_code WW6369 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2972 _journal_page_last o2973 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C16 H7 Cl2 F3 N4 O' _chemical_formula_moiety 'C16 H7 Cl2 F3 N4 O' _chemical_formula_sum 'C16 H7 Cl2 F3 N4 O' _chemical_formula_weight 399.16 _chemical_melting_point 450.0(10) _chemical_name_systematic ; 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]- 1H-pyrazole-3-carbonitrile ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 92.0840(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.8828(9) _cell_length_b 6.7072(5) _cell_length_c 21.1191(16) _cell_measurement_reflns_used 3298 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.02 _cell_measurement_theta_min 3.18 _cell_volume 1682.1(2) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \w' _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 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 8571 _diffrn_reflns_theta_full 25.19 _diffrn_reflns_theta_max 25.19 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.430 _exptl_absorpt_correction_T_max 0.8854 _exptl_absorpt_correction_T_min 0.8535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _refine_diff_density_max 1.122 _refine_diff_density_min -0.644 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3013 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0688 _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^)+(0.1164P)^2^+2.0094P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1953 _refine_ls_wR_factor_ref 0.2039 _reflns_number_gt 2571 _reflns_number_total 3013 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6369.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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 1527 2010-12-29 10:47:43Z saulius 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2206812 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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.58604(10) 0.09721(15) 0.17137(5) 0.0678(4) Uani d . 1 Cl Cl2 0.60827(9) 0.75002(15) 0.02417(5) 0.0637(4) Uani d . 1 Cl F1 0.2558(5) 0.7800(15) 0.1718(6) 0.293(6) Uani d . 1 F F2 0.1880(3) 0.6094(13) 0.1130(2) 0.206(3) Uani d . 1 F F3 0.2255(5) 0.5229(17) 0.2002(4) 0.308(7) Uani d . 1 F O1 0.8328(2) 0.9534(4) 0.21212(12) 0.0528(6) Uani d . 1 O N1 0.6953(2) 0.3706(4) 0.08051(14) 0.0438(7) Uani d . 1 N N2 0.7008(2) 0.2090(4) 0.04282(14) 0.0485(7) Uani d . 1 N N3 0.8761(4) -0.1086(6) -0.0323(2) 0.0843(13) Uani d . 1 N N4 0.8054(2) 0.6190(4) 0.13362(14) 0.0450(7) Uani d . 1 N C1 0.2601(4) 0.5992(10) 0.1540(3) 0.0871(16) Uani d . 1 C C2 0.3750(3) 0.5423(7) 0.13571(18) 0.0580(10) Uani d . 1 C C3 0.4202(3) 0.3669(6) 0.15846(19) 0.0561(9) Uani d . 1 C H3 0.3797 0.2856 0.1851 0.067 Uiso calc R 1 H C4 0.5269(3) 0.3135(5) 0.14114(17) 0.0466(8) Uani d . 1 C C5 0.5876(3) 0.4327(5) 0.10036(16) 0.0412(7) Uani d . 1 C C6 0.5386(3) 0.6063(5) 0.07742(17) 0.0455(8) Uani d . 1 C C7 0.4320(3) 0.6633(6) 0.09581(19) 0.0560(9) Uani d . 1 C H7 0.3999 0.7819 0.0811 0.067 Uiso calc R 1 H C8 0.8478(3) 0.0251(6) -0.0030(2) 0.0597(10) Uani d . 1 C C9 0.8111(3) 0.1898(6) 0.03400(17) 0.0499(8) Uani d . 1 C C10 0.8752(3) 0.3377(6) 0.06397(18) 0.0513(9) Uani d . 1 C H10 0.9529 0.3542 0.0636 0.062 Uiso calc R 1 H C11 0.7988(3) 0.4543(5) 0.09428(16) 0.0430(7) Uani d . 1 C C12 0.8959(3) 0.7205(5) 0.13453(16) 0.0456(8) Uani d . 1 C H12 0.9534 0.6794 0.1088 0.055 Uiso calc R 1 H C13 0.9146(3) 0.8937(5) 0.17273(16) 0.0437(8) Uani d . 1 C C14 1.0007(3) 1.0250(6) 0.17631(19) 0.0568(10) Uani d . 1 C H14 1.0670 1.0174 0.1544 0.068 Uiso calc R 1 H C15 0.9719(3) 1.1751(6) 0.21907(18) 0.0545(9) Uani d . 1 C H15 1.0145 1.2862 0.2309 0.065 Uiso calc R 1 H C16 0.8701(3) 1.1248(6) 0.23926(19) 0.0551(9) Uani d . 1 C H16 0.8302 1.1985 0.2682 0.066 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0748(7) 0.0525(6) 0.0762(7) 0.0074(5) 0.0035(5) 0.0156(5) Cl2 0.0673(7) 0.0498(6) 0.0738(7) -0.0100(4) -0.0003(5) 0.0125(4) F1 0.102(4) 0.302(9) 0.480(15) 0.047(5) 0.068(6) -0.226(11) F2 0.0508(19) 0.412(10) 0.155(4) 0.073(4) -0.001(2) -0.024(5) F3 0.159(5) 0.473(14) 0.304(8) 0.202(7) 0.174(6) 0.256(10) O1 0.0416(13) 0.0535(15) 0.0642(15) 0.0001(11) 0.0142(11) -0.0077(12) N1 0.0393(15) 0.0376(15) 0.0547(16) 0.0007(11) 0.0041(12) -0.0068(12) N2 0.0458(16) 0.0419(16) 0.0579(17) 0.0016(12) 0.0053(13) -0.0091(13) N3 0.080(3) 0.074(3) 0.102(3) 0.000(2) 0.034(2) -0.034(2) N4 0.0385(14) 0.0428(16) 0.0538(16) 0.0012(12) 0.0023(12) -0.0051(13) C1 0.056(3) 0.124(5) 0.082(3) 0.034(3) 0.017(3) -0.004(3) C2 0.0409(19) 0.079(3) 0.054(2) 0.0093(18) 0.0019(16) -0.009(2) C3 0.046(2) 0.066(2) 0.056(2) -0.0039(17) 0.0063(16) -0.0006(18) C4 0.0426(18) 0.0459(19) 0.0511(19) 0.0003(15) -0.0008(14) -0.0011(15) C5 0.0346(16) 0.0391(17) 0.0497(18) 0.0000(13) 0.0009(13) -0.0075(14) C6 0.0439(18) 0.0389(18) 0.0536(19) -0.0037(14) -0.0027(15) -0.0060(15) C7 0.051(2) 0.050(2) 0.066(2) 0.0145(17) -0.0075(17) -0.0089(18) C8 0.055(2) 0.056(2) 0.069(2) 0.0019(18) 0.0138(18) -0.010(2) C9 0.0489(19) 0.047(2) 0.054(2) 0.0075(16) 0.0067(15) -0.0052(16) C10 0.0387(17) 0.055(2) 0.061(2) 0.0033(16) 0.0083(15) -0.0065(17) C11 0.0367(16) 0.0439(18) 0.0487(18) 0.0017(13) 0.0036(13) -0.0011(14) C12 0.0354(16) 0.051(2) 0.0507(19) 0.0041(14) 0.0065(14) -0.0046(15) C13 0.0349(16) 0.0479(19) 0.0486(18) 0.0029(13) 0.0051(13) -0.0006(15) C14 0.0438(19) 0.062(2) 0.066(2) -0.0085(17) 0.0127(16) -0.0113(19) C15 0.054(2) 0.051(2) 0.058(2) -0.0050(17) 0.0017(16) -0.0067(17) C16 0.056(2) 0.051(2) 0.059(2) 0.0043(17) 0.0096(17) -0.0107(17) 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' F F 0.0171 0.0103 '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_publ_flag C16 O1 C13 106.2(3) yes N2 N1 C11 113.0(3) yes N2 N1 C5 118.2(3) ? C11 N1 C5 128.7(3) ? C9 N2 N1 103.2(3) yes C12 N4 C11 117.7(3) ? F3 C1 F2 111.0(7) yes F3 C1 F1 98.6(8) ? F2 C1 F1 97.1(7) ? F3 C1 C2 116.9(5) ? F2 C1 C2 117.8(5) ? F1 C1 C2 111.8(6) ? C7 C2 C3 121.9(3) ? C7 C2 C1 119.3(4) ? C3 C2 C1 118.8(4) ? C2 C3 C4 118.8(4) ? C2 C3 H3 120.6 ? C4 C3 H3 120.6 ? C3 C4 C5 121.0(3) ? C3 C4 Cl1 119.1(3) ? C5 C4 Cl1 119.9(3) ? C6 C5 C4 118.6(3) ? C6 C5 N1 121.0(3) ? C4 C5 N1 120.3(3) ? C5 C6 C7 120.6(3) ? C5 C6 Cl2 119.7(3) ? C7 C6 Cl2 119.6(3) ? C2 C7 C6 119.0(4) ? C2 C7 H7 120.5 ? C6 C7 H7 120.5 ? N3 C8 C9 179.1(5) yes N2 C9 C10 113.1(3) yes N2 C9 C8 118.1(3) ? C10 C9 C8 128.8(3) ? C11 C10 C9 104.9(3) yes C11 C10 H10 127.5 ? C9 C10 H10 127.5 ? C10 C11 N1 105.7(3) yes C10 C11 N4 135.3(3) ? N1 C11 N4 118.9(3) ? N4 C12 C13 123.9(3) ? N4 C12 H12 118.0 ? C13 C12 H12 118.0 ? C14 C13 O1 109.3(3) yes C14 C13 C12 131.6(3) ? O1 C13 C12 119.0(3) ? C13 C14 C15 107.6(3) yes C13 C14 H14 126.2 ? C15 C14 H14 126.2 ? C16 C15 C14 105.6(3) yes C16 C15 H15 127.2 ? C14 C15 H15 127.2 ? C15 C16 O1 111.4(3) yes C15 C16 H16 124.3 ? O1 C16 H16 124.3 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C4 1.724(4) yes Cl2 C6 1.716(4) ? F1 C1 1.271(9) yes F2 C1 1.198(7) ? F3 C1 1.188(7) ? O1 C16 1.352(4) yes O1 C13 1.362(4) yes N1 N2 1.348(4) yes N1 C11 1.374(4) yes N1 C5 1.423(4) ? N2 C9 1.337(5) yes N3 C8 1.147(5) yes N4 C12 1.273(4) yes N4 C11 1.382(4) yes C1 C2 1.483(6) ? C2 C7 1.367(6) ? C2 C3 1.373(6) ? C3 C4 1.380(5) ? C3 H3 0.9300 ? C4 C5 1.395(5) ? C5 C6 1.382(5) ? C6 C7 1.393(5) ? C7 H7 0.9300 ? C8 C9 1.430(5) ? C9 C10 1.389(5) yes C10 C11 1.374(5) yes C10 H10 0.9300 ? C12 C13 1.427(5) ? C12 H12 0.9300 ? C13 C14 1.350(5) yes C14 C15 1.403(5) yes C14 H14 0.9300 ? C15 C16 1.340(6) yes C15 H15 0.9300 ? C16 H16 0.9300 ?