#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008191.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_2008191 loop_ _publ_author_name 'Susmita Gupta' 'Jayanta Kumar Ray' 'Kandasamy Chinnakali' 'Hoong-Kun Fun' _publ_section_title ; (E)-1,2-Bis(2-chlorocyclopentenyl)ethene ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900012 _journal_paper_doi 10.1107/S0108270199099801 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C12 H14 Cl2' _chemical_formula_weight 229.13 _chemical_name_systematic ; E-1,2-(Di-2'-chlorocyclopentenyl)ethylene ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.060(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.1458(2) _cell_length_b 12.5203(4) _cell_length_c 11.1023(4) _cell_measurement_reflns_used 2802 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.45 _cell_measurement_theta_min 2.47 _cell_volume 567.42(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _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 0.099 _diffrn_reflns_av_sigmaI/netI 0.081 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4434 _diffrn_reflns_theta_max 28.45 _diffrn_reflns_theta_min 2.47 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_type 'empirical (SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.35 _refine_diff_density_min -0.68 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1402 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.923 _refine_ls_R_factor_all 0.088 _refine_ls_R_factor_gt 0.064 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1054P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.172 _reflns_number_gt 906 _reflns_number_total 1402 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0087.cif _cod_data_source_block qa0087 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008191 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 Cl1 -0.0110(2) 0.70282(5) 0.90357(7) 0.0591(3) Uani d . 1 . . Cl C1 0.0811(7) 0.81439(19) 0.8250(2) 0.0418(6) Uani d . 1 . . C C2 0.0760(6) 0.91496(19) 0.8660(2) 0.0406(6) Uani d . 1 . . C C3 0.1747(8) 0.9899(2) 0.7728(3) 0.0469(7) Uani d . 1 . . C C4 0.2103(11) 0.9188(2) 0.6623(3) 0.0582(8) Uani d . 1 . . C C5 0.1763(9) 0.8027(2) 0.7013(3) 0.0502(7) Uani d . 1 . . C C6 -0.0037(7) 0.94925(19) 0.9812(2) 0.0423(6) Uani d . 1 . . C H3A 0.013(8) 1.034(3) 0.746(3) 0.067(11) Uiso d . 1 . . H H3B 0.372(7) 1.025(2) 0.807(3) 0.045(8) Uiso d . 1 . . H H4A 0.045(9) 0.938(3) 0.594(4) 0.093(14) Uiso d . 1 . . H H4B 0.415(11) 0.931(4) 0.643(4) 0.108(14) Uiso d . 1 . . H H5A 0.002(7) 0.767(3) 0.648(3) 0.054(8) Uiso d . 1 . . H H5B 0.371(8) 0.757(3) 0.702(3) 0.069(9) Uiso d . 1 . . H H6 -0.070(7) 0.902(2) 1.031(3) 0.047(7) Uiso d . 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 0.0953(7) 0.0284(4) 0.0554(5) -0.0047(3) 0.0184(4) 0.0018(2) C1 0.0571(15) 0.0294(11) 0.0389(13) 0.0028(10) 0.0090(11) -0.0010(9) C2 0.0512(14) 0.0276(11) 0.0435(13) 0.0036(10) 0.0101(11) -0.0016(10) C3 0.0626(19) 0.0335(13) 0.0468(15) 0.0029(12) 0.0154(13) 0.0010(11) C4 0.088(2) 0.0455(16) 0.0463(16) 0.0006(15) 0.0277(16) 0.0001(12) C5 0.0692(18) 0.0397(14) 0.0430(15) 0.0068(13) 0.0140(13) -0.0038(11) C6 0.0593(15) 0.0291(12) 0.0402(14) 0.0007(11) 0.0136(12) 0.0014(10) 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' 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_site_symmetry_1 _geom_angle C2 C1 C5 . 115.2(2) C2 C1 Cl1 . 124.8(2) C5 C1 Cl1 . 120.01(18) C1 C2 C6 . 126.9(2) C1 C2 C3 . 109.2(2) C6 C2 C3 . 123.8(2) C2 C3 C4 . 105.2(2) C2 C3 H3A . 110(2) C4 C3 H3A . 106(2) C2 C3 H3B . 109.8(17) C4 C3 H3B . 112.9(18) H3A C3 H3B . 113(3) C5 C4 C3 . 107.3(2) C5 C4 H4A . 112(2) C3 C4 H4A . 109(2) C5 C4 H4B . 111(3) C3 C4 H4B . 108(3) H4A C4 H4B . 109(3) C1 C5 C4 . 102.6(2) C1 C5 H5A . 108.6(18) C4 C5 H5A . 111(2) C1 C5 H5B . 113.5(19) C4 C5 H5B . 116(2) H5A C5 H5B . 105(3) C6 C6 C2 3_577 124.4(3) C6 C6 H6 3_577 115.8(19) C2 C6 H6 . 119.8(18) 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 Cl1 C1 . 1.725(3) yes C1 C2 . 1.340(3) yes C1 C5 . 1.501(4) yes C2 C6 . 1.441(4) yes C2 C3 . 1.506(4) yes C3 C4 . 1.543(4) yes C3 H3A . 0.88(4) ? C3 H3B . 0.95(3) ? C4 C5 . 1.531(4) yes C4 H4A . 0.96(4) ? C4 H4B . 0.92(5) ? C5 H5A . 0.96(3) ? C5 H5B . 0.99(4) ? C6 C6 3_577 1.336(5) yes C6 H6 . 0.88(3) ? 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 C1 C2 C6 . -179.6(3) ? Cl1 C1 C2 C6 . 0.3(4) ? C5 C1 C2 C3 . -0.6(4) yes Cl1 C1 C2 C3 . 179.3(2) ? C1 C2 C3 C4 . 5.1(3) yes C6 C2 C3 C4 . -176.0(3) ? C2 C3 C4 C5 . -7.5(4) yes C2 C1 C5 C4 . -4.1(4) yes Cl1 C1 C5 C4 . 176.0(2) ? C3 C4 C5 C1 . 6.9(4) yes C1 C2 C6 C6 3_577 178.1(3) yes C3 C2 C6 C6 3_577 -0.7(5) ?