#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011397.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_2011397 loop_ _publ_author_name 'Pink, Maren' 'Britton, Doyle' 'Noland, Wayland E.' 'Pinnow, Matthew J.' _publ_section_title ; 2,4,6-Trichlorophenylisonitrile and 2,4,6-trichlorobenzonitrile ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1271 _journal_page_last 1273 _journal_paper_doi 10.1107/S0108270100010234 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C7 H2 Cl3 N' _chemical_formula_weight 206.45 _chemical_melting_point 353.5(5) _chemical_name_systematic ; 2,4,6-trichlorobenzonitrile ; _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' _audit_creation_method 'SHELXL + manual additions' _cell_angle_alpha 90.00 _cell_angle_beta 90.975(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.8742(3) _cell_length_b 15.8897(13) _cell_length_c 12.9067(11) _cell_measurement_reflns_used 4571 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.0 _cell_volume 794.42(11) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXLTL _computing_publication_material SHELXLTL _computing_structure_refinement SHELXLTL _computing_structure_solution 'SHELXTL (Sheldrick, 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device 'Siemens SMART area detector diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .028 _diffrn_reflns_av_sigmaI/netI .018 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8166 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.03 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_interval_time ; first 181 reflections remeasured at the end of the data collection 6 hours later ; _diffrn_standards_number 181 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_T_max .85 _exptl_absorpt_correction_T_min .70 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996; Blessing, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_meas ? _exptl_crystal_description needle _exptl_crystal_F_000 408 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .15 _refine_diff_density_max .295 _refine_diff_density_min -.182 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.08 _refine_ls_goodness_of_fit_obs 1.13 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1811 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.08 _refine_ls_restrained_S_obs 1.130 _refine_ls_R_factor_all .034 _refine_ls_R_factor_obs .026 _refine_ls_shift/esd_max .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+0.12P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .068 _refine_ls_wR_factor_obs .066 _reflns_number_observed 1542 _reflns_number_total 1811 _reflns_observed_criterion I>2\s(I) _cod_data_source_file bk1548.cif _cod_data_source_block nitrile _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '353-354' was changed to '353.5(5)' - 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 '353-354' was changed to '353.5(5)' - 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+0.12P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+0.12P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011397 _cod_database_fobs_code 2011397 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_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 Cl2 .74410(11) -.01756(2) .13222(3) .03703(12) Uani d . 1 . . Cl Cl4 .24707(10) .10423(3) .48775(3) .03804(12) Uani d . 1 . . Cl Cl6 .80198(11) .31520(2) .21253(3) .03809(12) Uani d . 1 . . Cl C1 .7467(4) .14791(9) .18029(11) .0254(3) Uani d . 1 . . C C2 .6551(4) .06659(9) .21132(12) .0269(3) Uani d . 1 . . C C3 .5002(4) .05265(10) .30585(11) .0290(3) Uani d . 1 . . C H3 .4389 -.0026 .3268 .035 Uiso calc R 1 . . H C4 .4367(4) .12135(10) .36926(12) .0282(3) Uani d . 1 . . C C5 .5233(4) .20275(10) .34168(12) .0291(3) Uani d . 1 . . C H5 .4770 .2489 .3862 .035 Uiso calc R 1 . . H C6 .6788(4) .21476(9) .24764(12) .0266(3) Uani d . 1 . . C C7 .9101(4) .16173(10) .08227(12) .0295(3) Uani d . 1 . . C N1 1.0432(4) .17258(9) .00522(11) .0394(3) Uani d . 1 . . N 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 Cl2 .0457(3) .0291(2) .0364(2) .00167(16) .00446(17) -.00609(15) Cl4 .0365(2) .0507(3) .0271(2) .00261(17) .00544(15) .00534(17) Cl6 .0440(2) .0265(2) .0439(2) -.00135(15) .00617(18) .00138(16) C1 .0223(7) .0294(8) .0245(7) .0024(5) -.0021(5) .0013(6) C2 .0251(7) .0271(7) .0283(7) .0024(6) -.0029(6) -.0017(6) C3 .0277(8) .0298(8) .0295(8) -.0003(6) -.0021(6) .0034(6) C4 .0235(7) .0380(8) .0230(7) .0012(6) -.0007(6) .0036(6) C5 .0266(8) .0333(8) .0275(7) .0038(6) -.0017(6) -.0037(6) C6 .0228(7) .0265(7) .0303(8) .0004(5) -.0023(6) .0010(6) C7 .0294(8) .0284(7) .0306(8) .0022(6) -.0005(6) .0003(6) N1 .0437(9) .0403(8) .0344(8) .0001(6) .0081(6) .0011(6) 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' Cl Cl .1484 .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 C2 C1 C6 118.1(2) C2 C1 C7 120.6(2) C6 C1 C7 121.3(2) C3 C2 C1 121.0(2) C3 C2 Cl2 119.5(2) C1 C2 Cl2 119.5(2) C2 C3 C4 118.5(2) C2 C3 H3 120.8 C4 C3 H3 120.8 C5 C4 C3 122.5(2) C5 C4 Cl4 118.9(2) C3 C4 Cl4 118.7(2) C6 C5 C4 117.9(2) C6 C5 H5 121.1 C4 C5 H5 121.1 C5 C6 C1 122.1(2) C5 C6 Cl6 119.1(2) C1 C6 Cl6 118.8(2) N1 C7 C1 179.2(2) 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 Cl2 C2 . 1.7208(15) ? Cl4 C4 . 1.7293(16) ? Cl6 C6 . 1.7284(15) ? C1 C2 . 1.400(2) ? C1 C6 . 1.400(2) ? C1 C7 . 1.441(2) ? C2 C3 . 1.387(2) ? C3 C4 . 1.389(2) ? C3 H3 . .9500 ? C4 C5 . 1.384(2) ? C5 C6 . 1.377(2) ? C5 H5 . .9500 ? C7 N1 . 1.141(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 455502 2 PubChem 522179