#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200516.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_2200516 loop_ _publ_author_name 'Britton, Doyle' _publ_section_title ; 2-Fluoro-6-iodobenzonitrile ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o702 _journal_page_last o704 _journal_paper_doi 10.1107/S1600536801010923 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C7 H3 F I N' _chemical_formula_weight 247.00 _chemical_name_systematic 2-fluoro-6-iodobenzonitrile _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'SHELXTL plus manual additions' _cell_angle_alpha 82.232(2) _cell_angle_beta 82.359(2) _cell_angle_gamma 62.242(2) _cell_formula_units_Z 4 _cell_length_a 8.0270(8) _cell_length_b 8.0435(8) _cell_length_c 13.8493(13) _cell_measurement_reflns_used 4333 _cell_measurement_temperature 174(2) _cell_measurement_theta_max 24.8 _cell_measurement_theta_min 4.0 _cell_volume 781.52(13) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1994)' _diffrn_ambient_temperature 174(2) _diffrn_measured_fraction_theta_full .990 _diffrn_measured_fraction_theta_max .990 _diffrn_measurement_device_type 'Siemens SMART area detector diffractometer' _diffrn_measurement_method \w _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 .0421 _diffrn_reflns_av_sigmaI/netI .0636 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5149 _diffrn_reflns_theta_full 24.88 _diffrn_reflns_theta_max 24.88 _diffrn_reflns_theta_min 1.49 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.035 _exptl_absorpt_correction_T_max .67 _exptl_absorpt_correction_T_min .23 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996; Blessing, 1995' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.099 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 456 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .10 _refine_diff_density_max 1.072 _refine_diff_density_min -1.487 _refine_ls_extinction_coef .0042(9) _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref .984 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2689 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .984 _refine_ls_R_factor_all .0485 _refine_ls_R_factor_gt .0433 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1093 _reflns_number_gt 2241 _reflns_number_total 2689 _reflns_threshold_expression >2\s(I) _cod_data_source_file om6026.cif _cod_data_source_block I _cod_depositor_comments ; 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_original_cell_volume 781.52(15) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2200516 _cod_database_fobs_code 2200516 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 C11 .5937(8) .1731(7) .9932(4) .0323(13) Uani d . 1 . . C C12 .6131(9) .1171(8) 1.0923(5) .0405(15) Uani d . 1 . . C C13 .7563(9) -.0514(8) 1.1275(5) .0422(15) Uani d . 1 . . C H13 .7649 -.0862 1.1956 .051 Uiso calc R 1 . . H C14 .8879(9) -.1685(8) 1.0588(5) .0420(15) Uani d . 1 . . C H14 .9884 -.2846 1.0808 .050 Uiso calc R 1 . . H C15 .8744(8) -.1183(7) .9584(4) .0356(13) Uani d . 1 . . C H15 .9646 -.2009 .9132 .043 Uiso calc R 1 . . H C16 .7289(7) .0532(7) .9242(4) .0297(12) Uani d . 1 . . C C17 .4378(8) .3517(8) .9629(5) .0375(14) Uani d . 1 . . C N1 .3139(8) .4922(7) .9413(5) .0538(15) Uani d . 1 . . N F1 .4826(6) .2349(6) 1.1569(3) .0592(11) Uani d . 1 . . F I1 .71568(5) .13079(5) .77437(3) .03923(19) Uani d . 1 . . I C21 -.0373(7) .7327(7) .5300(4) .0258(11) Uani d . 1 . . C C22 -.1832(8) .7908(7) .4690(4) .0315(12) Uani d . 1 . . C C23 -.3414(8) .7649(8) .4956(5) .0398(15) Uani d . 1 . . C H23 -.4378 .8054 .4522 .048 Uiso calc R 1 . . H C24 -.3556(8) .6783(8) .5873(5) .0448(16) Uani d . 1 . . C H24 -.4634 .6586 .6070 .054 Uiso calc R 1 . . H C25 -.2151(9) .6194(8) .6514(5) .0408(15) Uani d . 1 . . C H25 -.2280 .5610 .7144 .049 Uiso calc R 1 . . H C26 -.0560(7) .6463(7) .6230(4) .0286(12) Uani d . 1 . . C C27 .1227(8) .7652(7) .4949(4) .0276(11) Uani d . 1 . . C N2 .2498(7) .7919(7) .4631(4) .0398(12) Uani d . 1 . . N F2 -.1647(5) .8751(5) .3794(3) .0446(8) Uani d . 1 . . F I2 .15372(6) .56019(5) .72122(3) .04304(19) Uani d . 1 . . I 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 C11 .032(3) .026(2) .037(4) -.012(2) .000(2) -.002(2) C12 .043(3) .048(3) .031(4) -.021(3) .007(3) -.013(3) C13 .056(4) .046(3) .025(3) -.025(3) -.005(3) .005(3) C14 .045(3) .029(3) .046(4) -.013(3) -.007(3) .003(3) C15 .031(3) .031(3) .034(4) -.006(2) .002(2) -.003(2) C16 .028(3) .033(3) .029(3) -.014(2) -.002(2) -.004(2) C17 .033(3) .036(3) .043(4) -.013(3) -.004(3) -.013(3) N1 .045(3) .036(3) .071(5) -.006(3) -.014(3) -.016(3) F1 .062(2) .063(2) .039(2) -.019(2) .0154(19) -.0195(19) I1 .0413(3) .0410(3) .0274(3) -.01357(19) -.00255(17) .00255(17) C21 .023(3) .023(2) .030(3) -.009(2) .001(2) -.004(2) C22 .032(3) .026(3) .034(3) -.012(2) -.001(2) -.003(2) C23 .027(3) .039(3) .055(4) -.013(2) -.004(3) -.016(3) C24 .029(3) .045(3) .060(5) -.017(3) .013(3) -.018(3) C25 .046(4) .039(3) .033(4) -.018(3) .015(3) -.010(3) C26 .033(3) .027(2) .022(3) -.011(2) .001(2) -.007(2) C27 .030(3) .030(3) .023(3) -.013(2) -.004(2) -.002(2) N2 .036(3) .045(3) .042(3) -.023(2) -.008(2) .005(2) F2 .048(2) .056(2) .033(2) -.0261(17) -.0154(16) .0071(16) I2 .0549(3) .0411(3) .0282(3) -.0165(2) -.01199(19) .00089(17) 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' I I -.4742 1.8119 '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 C12 C11 C16 118.7(5) C12 C11 C17 119.6(5) C16 C11 C17 121.8(6) F1 C12 C13 119.2(6) F1 C12 C11 117.5(5) C13 C12 C11 123.3(5) C12 C13 C14 117.5(6) C12 C13 H13 121.3 C14 C13 H13 121.3 C15 C14 C13 121.3(5) C15 C14 H14 119.3 C13 C14 H14 119.3 C14 C15 C16 120.4(5) C14 C15 H15 119.8 C16 C15 H15 119.8 C15 C16 C11 118.8(5) C15 C16 I1 120.0(4) C11 C16 I1 121.1(4) N1 C17 C11 178.4(7) C22 C21 C26 117.8(5) C22 C21 C27 118.6(5) C26 C21 C27 123.6(5) F2 C22 C23 119.5(5) F2 C22 C21 117.5(5) C23 C22 C21 123.0(6) C22 C23 C24 118.0(6) C22 C23 H23 121.0 C24 C23 H23 121.0 C23 C24 C25 121.3(6) C23 C24 H24 119.3 C25 C24 H24 119.3 C26 C25 C24 119.8(6) C26 C25 H25 120.1 C24 C25 H25 120.1 C25 C26 C21 120.1(6) C25 C26 I2 119.5(4) C21 C26 I2 120.4(4) N2 C27 C21 177.5(6) 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 C11 C12 . 1.391(9) ? C11 C16 . 1.421(7) ? C11 C17 . 1.452(8) ? C12 F1 . 1.360(7) ? C12 C13 . 1.384(9) ? C13 C14 . 1.399(9) ? C13 H13 . .9500 ? C14 C15 . 1.398(9) ? C14 H14 . .9500 ? C15 C16 . 1.400(7) ? C15 H15 . .9500 ? C16 I1 . 2.087(6) ? C17 N1 . 1.139(7) ? C21 C22 . 1.397(8) ? C21 C26 . 1.402(7) ? C21 C27 . 1.437(8) ? C22 F2 . 1.357(7) ? C22 C23 . 1.375(8) ? C23 C24 . 1.381(10) ? C23 H23 . .9500 ? C24 C25 . 1.393(10) ? C24 H24 . .9500 ? C25 C26 . 1.390(8) ? C25 H25 . .9500 ? C26 I2 . 2.106(6) ? C27 N2 . 1.158(7) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 455971 2 PubChem 168308587