#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012499.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_2012499 loop_ _publ_author_name 'Boitsov, Stepan' 'Songstad, Jon' 'T\"ornroos, Karl W.' _publ_section_title ; 4-(Trifluoromethyl)benzonitrile ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o66 _journal_page_last o68 _journal_paper_doi 10.1107/S0108270101019540 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C8 H4 F3 N' _chemical_formula_sum 'C8 H4 F3 N' _chemical_formula_weight 171.12 _chemical_melting_point 313.0(10) _chemical_name_common 4-trifluoromethylbenzonitrile _chemical_name_systematic 4-(trifluoromethyl)benzonitrile _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 SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 102.835(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2189(6) _cell_length_b 6.0621(3) _cell_length_c 15.0977(10) _cell_measurement_reflns_used 4972 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 31.5 _cell_measurement_theta_min 2.6 _cell_volume 733.43(8) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1997a)' _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Bruker SMART 2K CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .029 _diffrn_reflns_av_sigmaI/netI .023 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12772 _diffrn_reflns_theta_full 31.46 _diffrn_reflns_theta_max 31.5 _diffrn_reflns_theta_min 2.6 _diffrn_standards_decay_% 0 _diffrn_standards_number 105 _exptl_absorpt_coefficient_mu .146 _exptl_absorpt_correction_T_max .988 _exptl_absorpt_correction_T_min .947 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(SHELXTL/PC; Sheldrick 1997a)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 344 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .25 _refine_diff_density_max .30 _refine_diff_density_min -.40 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 2417 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all .053 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.0443P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .110 _refine_ls_wR_factor_ref .115 _reflns_number_gt 1835 _reflns_number_total 2417 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gg1086.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_cif_authors_sg_Hall -P2yn _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '312-314' was changed to '313.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '312-314' was changed to '313.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2012499 _cod_database_fobs_code 2012499 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol F1 1.05225(10) .11424(14) .25672(5) .0457(2) Uani d . 1 . . F F2 .91875(10) .03120(12) .35907(5) .0419(2) Uani d . 1 . . F F3 .84468(9) .31119(13) .27290(5) .0426(2) Uani d . 1 . . F N 1.50418(13) .87351(17) .61878(6) .0346(2) Uani d . 1 . . N C1 1.30643(12) .61636(17) .50577(6) .0225(2) Uani d . 1 . . C C2 1.25432(13) .67997(17) .41489(7) .0256(2) Uani d . 1 . . C H2 1.2922 .8148 .3945 .031 Uiso calc R 1 . . H C3 1.14659(13) .54429(17) .35452(6) .0252(2) Uani d . 1 . . C H3 1.1096 .5861 .2927 .030 Uiso calc R 1 . . H C4 1.09343(12) .34637(16) .38561(6) .02092(19) Uani d . 1 . . C C5 1.14720(13) .28124(17) .47580(7) .0246(2) Uani d . 1 . . C H5 1.1110 .1448 .4957 .030 Uiso calc R 1 . . H C6 1.25416(13) .41693(17) .53667(6) .0253(2) Uani d . 1 . . C H6 1.2912 .3746 .5985 .030 Uiso calc R 1 . . H C7 1.41723(13) .75943(18) .56882(7) .0266(2) Uani d . 1 . . C C8 .97776(13) .20115(17) .31900(6) .0253(2) Uani d . 1 . . C 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 F1 .0448(4) .0590(5) .0351(4) -.0105(4) .0125(3) -.0244(4) F2 .0506(4) .0407(4) .0291(3) -.0221(3) -.0025(3) .0041(3) F3 .0349(4) .0414(4) .0404(4) .0020(3) -.0158(3) -.0002(3) N .0373(5) .0390(5) .0260(5) -.0081(4) .0040(4) -.0042(4) C1 .0209(4) .0265(5) .0194(4) -.0005(3) .0032(3) -.0030(3) C2 .0287(5) .0259(5) .0216(4) -.0034(4) .0042(4) .0025(4) C3 .0287(5) .0275(5) .0178(4) -.0010(4) .0019(3) .0029(3) C4 .0201(4) .0251(5) .0167(4) .0003(3) .0022(3) -.0003(3) C5 .0279(5) .0260(5) .0190(4) -.0033(4) .0032(4) .0032(3) C6 .0275(5) .0302(5) .0165(4) -.0020(4) .0013(3) .0015(3) C7 .0267(5) .0305(5) .0225(5) -.0022(4) .0053(4) -.0017(4) C8 .0272(5) .0272(5) .0199(4) -.0022(4) .0021(4) .0001(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 '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 C2 C1 C6 121.10(9) yes C2 C1 C7 119.35(9) yes C6 C1 C7 119.54(9) yes C1 C2 C3 119.47(9) yes C2 C3 C4 119.36(9) yes C3 C4 C4 121.23(9) yes C3 C4 C8 118.52(8) yes C5 C4 C8 120.25(9) yes C4 C5 C6 119.69(9) yes C1 C6 C5 119.14(9) yes N C7 C1 179.59(12) yes F1 C8 F2 106.41(9) yes F1 C8 F3 106.23(8) yes F2 C8 F3 106.41(9) yes F1 C8 C4 112.33(9) yes F2 C8 C4 112.74(8) yes F3 C8 C4 112.22(8) yes C1 C2 H2 120.3 ? C3 C2 H2 120.3 ? C2 C3 H3 120.3 ? C4 C3 H3 120.3 ? C4 C5 H5 120.2 ? C6 C5 H5 120.2 ? C1 C6 H6 120.4 ? C5 C6 H6 120.4 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.3978(13) yes C1 C6 . 1.3975(14) yes C1 C7 . 1.4500(13) yes C2 C3 . 1.3902(14) yes C3 C4 . 1.3935(14) yes C4 C5 . 1.3922(13) yes C4 C8 . 1.5050(13) yes C5 C6 . 1.3911(14) yes C7 N . 1.1482(14) yes C8 F1 . 1.3388(13) yes C8 F2 . 1.3390(12) yes C8 F3 . 1.3370(12) yes C2 H2 . .9500 ? C3 H3 . .9500 ? C5 H5 . .9500 ? C6 H6 . .9500 ? 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 C6 C1 C2 C3 1.03(15) C7 C1 C2 C3 -179.28(10) C1 C2 C3 C4 -.46(15) C2 C3 C4 C5 -.50(15) C2 C3 C4 C8 -179.58(9) C3 C4 C5 C6 .90(15) C8 C4 C5 C6 179.97(10) C4 C5 C6 C1 -.34(15) C2 C1 C6 C5 -.63(15) C7 C1 C6 C5 179.68(9) C5 C4 C8 F3 129.20(10) C3 C4 C8 F3 -51.71(13) C5 C4 C8 F1 -111.18(11) C3 C4 C8 F1 67.91(12) C5 C4 C8 F2 9.05(14) C3 C4 C8 F2 -171.86(9)