#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102126.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_2102126 loop_ _publ_author_name 'Britton, Doyle' 'Noland, Wayland E.' 'Pinnow, Matthew J.' _publ_section_title ; Isomorphism and pseudosymmetry in 2,6-dichloro- and 2,6-dibromobenzonitrile ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 822 _journal_page_last 827 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C7 H3 Br2 N' _chemical_formula_weight 260.92 _chemical_name_systematic ; 2,6-dibromobenzonitrile ; _space_group_IT_number 12 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2y' _symmetry_space_group_name_H-M 'C 1 2/m 1' _audit_creation_method 'SHELXTL plus manual additions' _cell_angle_alpha 90.00 _cell_angle_beta 101.446(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 18.2269(15) _cell_length_b 21.349(2) _cell_length_c 3.9663(3) _cell_measurement_reflns_used 2694 _cell_measurement_temperature 174(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 1.5 _cell_volume 1512.7(2) _computing_cell_refinement SAINT _computing_data_collection 'SAINT (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_measurement_device 'Siemens SMART area detector' _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 .033 _diffrn_reflns_av_sigmaI/netI .038 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 3985 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 1.49 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_interval_time ; the first 131 reflections were remeasured at the end of the data collection 6 hours later ; _diffrn_standards_number 131 _exptl_absorpt_coefficient_mu 10.631 _exptl_absorpt_correction_T_max .183 _exptl_absorpt_correction_T_min .086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996; Blessing, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.291 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'thick needle' _exptl_crystal_F_000 976 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .21 _exptl_crystal_size_min .16 _refine_diff_density_max .991 _refine_diff_density_min -1.069 _refine_ls_extinction_coef .0014(2) _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_all 1.13 _refine_ls_goodness_of_fit_obs 1.19 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1378 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.13 _refine_ls_restrained_S_obs 1.19 _refine_ls_R_factor_all .045 _refine_ls_R_factor_obs .036 _refine_ls_shift/esd_max -.001 _refine_ls_shift/esd_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.9400P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all .104 _refine_ls_wR_factor_obs .100 _reflns_number_observed 1148 _reflns_number_total 1378 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file bk0072.cif _[local]_cod_data_source_block Br2 _cod_database_code 2102126 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' 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' Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br12 .35939(3) .24585(2) .19831(13) .0243(2) Uani d . 1 Br N11 .5000 .1362(3) .0000 .038(2) Uani d S 1 N C11 .5000 .2567(3) .0000 .0182(14) Uani d S 1 C C12 .4402(2) .2904(2) .0864(11) .0188(10) Uani d . 1 C C13 .4401(3) .3559(2) .0843(12) .0245(11) Uani d . 1 C H13 .3992(3) .3784(2) .1402(12) .029 Uiso calc R 1 H C14 .5000 .3874(3) .0000 .030(2) Uani d S 1 C H14 .5000 .4319(3) .0000 .036 Uiso calc SR 1 H C17 .5000 .1901(3) .0000 .024(2) Uani d S 1 C Br22 .24603(3) .13240(2) .51581(12) .0267(2) Uani d . 1 Br N21 .1297(4) .0000 .6772(18) .037(2) Uani d S 1 N C21 .2566(3) .0000 .4871(14) .0184(14) Uani d S 1 C C22 .2923(3) .0560(2) .4366(11) .0196(10) Uani d . 1 C C23 .3616(2) .0562(2) .3386(11) .0221(11) Uani d . 1 C H23 .3860(2) .0945(2) .3092(11) .027 Uiso calc R 1 H C24 .3936(4) .0000 .2856(18) .029(2) Uani d S 1 C H24 .4398(4) .0000 .2091(18) .035 Uiso calc SR 1 H C27 .1857(4) .0000 .5918(17) .0211(14) Uani d S 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 Br12 .0177(4) .0237(4) .0345(4) -.0025(2) .0123(3) -.0023(2) N11 .033(4) .019(4) .068(5) .000 .026(4) .000 C11 .017(4) .013(3) .024(4) .000 .003(3) .000 C12 .012(2) .021(2) .025(2) -.005(2) .006(2) .001(2) C13 .017(3) .022(2) .035(3) .003(2) .006(2) -.006(2) C14 .026(4) .015(4) .048(5) .000 .007(4) .000 C17 .016(4) .025(4) .034(4) .000 .012(3) .000 Br22 .0293(4) .0158(3) .0384(4) -.0001(2) .0150(3) -.0007(2) N21 .036(4) .034(4) .048(4) .000 .024(3) .000 C21 .014(3) .022(4) .020(3) .000 .004(3) .000 C22 .023(3) .015(2) .021(2) .002(2) .004(2) .001(2) C23 .014(2) .025(3) .027(3) -.004(2) .006(2) .002(2) C24 .013(4) .041(5) .037(4) .000 .013(3) .000 C27 .020(4) .012(3) .033(4) .000 .010(3) .000 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance Br12 C12 . 1.879(4) N11 C17 . 1.150(9) C11 C12 . 1.404(5) C11 C12 2_655 1.404(5) C11 C17 . 1.423(9) C12 C13 . 1.398(7) C13 C14 . 1.379(6) C13 H13 . .95 C14 C13 2_655 1.379(6) C14 H14 . .95 Br22 C22 . 1.892(4) N21 C27 . 1.138(9) C21 C22 . 1.394(5) C21 C22 6 1.394(5) C21 C27 . 1.434(8) C22 C23 . 1.393(6) C23 C24 . 1.369(6) C23 H23 . .95 C24 C23 6 1.369(6) C24 H24 . .95 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C12 C11 C12 . 2_655 118.3(5) C12 C11 C17 . . 120.8(3) C12 C11 C17 2_655 . 120.8(3) C13 C12 C11 . . 120.8(4) C13 C12 Br12 . . 120.5(3) C11 C12 Br12 . . 118.7(3) C14 C13 C12 . . 119.2(5) C14 C13 H13 . . 120.4(3) C12 C13 H13 . . 120.4(3) C13 C14 C13 . 2_655 121.6(6) C13 C14 H14 . . 119.2(3) C13 C14 H14 2_655 . 119.2(3) N11 C17 C11 . . 180.0 C22 C21 C22 . 6 118.0(5) C22 C21 C27 . . 121.0(3) C22 C21 C27 6 . 121.0(3) C23 C22 C21 . . 121.2(4) C23 C22 Br22 . . 120.1(4) C21 C22 Br22 . . 118.7(3) C24 C23 C22 . . 118.5(5) C24 C23 H23 . . 120.8(3) C22 C23 H23 . . 120.8(3) C23 C24 C23 . 6 122.5(6) C23 C24 H24 . . 118.7(3) C23 C24 H24 6 . 118.7(3) N21 C27 C21 . . 179.5(8)