#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206017.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_2206017 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'McSweeney, Nigel' 'Pratt, Albert C.' 'Long, Conor' 'Howie, R. Alan' _publ_section_title ; 4',5',6',7'-Tetrachlorospiro[cyclohex-2-ene-1,2'-indan]-1',3'-dione ; _journal_issue 6 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1904 _journal_page_last o1906 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C14 H8 Cl4 O2' _chemical_formula_moiety 'C14 H8 Cl4 O2' _chemical_formula_sum 'C14 H8 Cl4 O2' _chemical_formula_weight 350.00 _chemical_melting_point .401E-305 _chemical_name_systematic ; 4',5',6',7'-Tetrachlorospiro[cyclohex-2-ene-1,2'-indan]-1',3'-dione ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 91.25(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.707(6) _cell_length_b 12.103(8) _cell_length_c 10.800(6) _cell_measurement_reflns_used 14 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 10.6 _cell_measurement_theta_min 7.7 _cell_volume 1399.2(14) _computing_cell_refinement 'Nicolet P3 software' _computing_data_collection 'Nicolet P3 software (Nicolet, 1980)' _computing_data_reduction 'RDNIC (Howie, 1980)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nicolet P3 four-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1632 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3222 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 1.90 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.841 _exptl_absorpt_correction_T_max 0.845 _exptl_absorpt_correction_T_min 0.565 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.353 _refine_diff_density_min -0.308 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 3222 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.997 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0704 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.102P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1691 _refine_ls_wR_factor_ref 0.1977 _reflns_number_gt 1634 _reflns_number_total 3222 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6435.cif 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_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' O O 0.0106 0.0060 '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_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 0.42407(12) 0.27220(12) 0.56551(12) 0.0807(4) Uani d . 1 . . Cl Cl2 0.26701(12) 0.39876(13) 0.36470(16) 0.0964(5) Uani d . 1 . . Cl Cl3 0.39920(16) 0.53456(14) 0.16260(14) 0.1076(6) Uani d . 1 . . Cl Cl4 0.68790(16) 0.54769(13) 0.15811(12) 0.0962(5) Uani d . 1 . . Cl O1 0.9009(3) 0.4407(3) 0.3086(3) 0.0906(11) Uani d . 1 . . O O2 0.7026(3) 0.2471(3) 0.6235(4) 0.0966(12) Uani d . 1 . . O C1 0.8496(4) 0.3105(4) 0.4690(4) 0.0613(11) Uani d . 1 B . C C2 0.8224(4) 0.3959(4) 0.3681(4) 0.0603(11) Uani d . 1 . . C C3 0.6848(4) 0.4098(3) 0.3562(4) 0.0512(10) Uani d . 1 . . C C4 0.6158(5) 0.4693(3) 0.2691(4) 0.0601(11) Uani d . 1 . . C C5 0.4859(5) 0.4653(4) 0.2719(4) 0.0669(13) Uani d . 1 . . C C6 0.4279(4) 0.4035(4) 0.3622(4) 0.0603(11) Uani d . 1 . . C C7 0.4971(4) 0.3466(3) 0.4518(4) 0.0547(10) Uani d . 1 . . C C8 0.6262(4) 0.3494(3) 0.4455(3) 0.0493(9) Uani d . 1 . . C C9 0.7226(4) 0.2951(4) 0.5276(4) 0.0618(11) Uani d . 1 . . C C10 0.9483(4) 0.3491(4) 0.5627(4) 0.0704(13) Uani d . 1 . . C H10 0.9378 0.4171 0.6012 0.084 Uiso calc R 1 . . H C11 1.0475(5) 0.2905(5) 0.5912(5) 0.0806(15) Uani d . 1 B . C H11 1.1051 0.3211 0.6471 0.097 Uiso calc R 1 . . H C12 1.0753(5) 0.1795(4) 0.5418(5) 0.0883(16) Uani d D 1 . . C H12A 1.1062 0.1325 0.6085 0.106 Uiso calc PR 0.50 A 1 H H12B 1.1401 0.1852 0.4807 0.106 Uiso calc PR 0.50 A 1 H H12C 1.0471 0.1237 0.5993 0.106 Uiso calc PR 0.50 A 2 H H12D 1.1649 0.1713 0.5337 0.106 Uiso calc PR 0.50 A 2 H C13A 0.9592(9) 0.1280(8) 0.4827(10) 0.082(3) Uani d PD 0.50 B 1 C H13A 0.9845 0.0660 0.4322 0.098 Uiso calc PR 0.50 B 1 H H13B 0.9074 0.0992 0.5479 0.098 Uiso calc PR 0.50 B 1 H C13B 1.0123(9) 0.1623(11) 0.4184(8) 0.080(3) Uani d PD 0.50 B 2 C H13C 1.0615 0.1987 0.3560 0.096 Uiso calc PR 0.50 B 2 H H13D 1.0126 0.0838 0.4001 0.096 Uiso calc PR 0.50 B 2 H C14 0.8849(5) 0.2020(5) 0.4070(6) 0.101(2) Uani d D 1 . . C H14A 0.8088 0.1640 0.3815 0.121 Uiso calc PR 0.50 B 1 H H14B 0.9307 0.2187 0.3327 0.121 Uiso calc PR 0.50 B 1 H H14C 0.8310 0.1449 0.4391 0.121 Uiso calc PR 0.50 B 2 H H14D 0.8649 0.2091 0.3193 0.121 Uiso calc PR 0.50 B 2 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 0.0699(8) 0.0889(9) 0.0838(8) -0.0202(7) 0.0105(6) 0.0018(7) Cl2 0.0533(7) 0.1046(11) 0.1306(13) 0.0062(7) -0.0184(7) -0.0185(9) Cl3 0.1207(13) 0.1032(12) 0.0969(11) 0.0347(9) -0.0414(9) 0.0129(8) Cl4 0.1232(13) 0.1006(11) 0.0647(8) -0.0101(9) 0.0021(8) 0.0265(7) O1 0.072(2) 0.118(3) 0.082(2) -0.032(2) 0.0081(19) -0.001(2) O2 0.080(2) 0.119(3) 0.089(3) -0.012(2) -0.018(2) 0.050(2) C1 0.049(2) 0.068(3) 0.066(3) 0.001(2) -0.015(2) -0.012(2) C2 0.055(3) 0.070(3) 0.056(3) -0.014(2) 0.000(2) -0.016(2) C3 0.059(2) 0.051(2) 0.043(2) -0.0055(19) -0.0059(18) -0.0110(18) C4 0.074(3) 0.055(3) 0.051(2) -0.006(2) -0.007(2) -0.005(2) C5 0.087(4) 0.053(3) 0.060(3) 0.015(2) -0.024(2) -0.009(2) C6 0.054(2) 0.055(3) 0.071(3) 0.001(2) -0.006(2) -0.020(2) C7 0.062(3) 0.046(2) 0.055(2) -0.0013(19) -0.001(2) -0.0098(18) C8 0.053(2) 0.045(2) 0.049(2) 0.0008(18) -0.0028(18) -0.0078(18) C9 0.062(3) 0.059(3) 0.063(3) -0.004(2) -0.011(2) 0.004(2) C10 0.057(3) 0.071(3) 0.083(3) -0.004(2) -0.018(2) -0.022(3) C11 0.060(3) 0.104(4) 0.077(3) -0.008(3) -0.014(2) -0.018(3) C12 0.074(3) 0.082(4) 0.108(4) 0.009(3) -0.017(3) 0.002(3) C13A 0.089(9) 0.069(7) 0.089(8) 0.005(6) 0.009(7) -0.016(6) C13B 0.086(8) 0.090(8) 0.063(6) 0.019(7) -0.001(6) -0.007(6) C14 0.086(4) 0.092(4) 0.123(5) 0.010(3) -0.025(4) -0.048(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C7 1.724(4) ? Cl2 C6 1.724(5) ? Cl3 C5 1.706(5) ? Cl4 C4 1.725(5) ? O1 C2 1.199(5) ? O2 C9 1.211(5) ? C1 C10 1.521(6) y C1 C9 1.524(6) y C1 C14 1.525(6) y C1 C2 1.525(6) y C2 C3 1.485(6) ? C3 C8 1.373(5) ? C3 C4 1.386(6) ? C4 C5 1.392(7) ? C5 C6 1.386(7) ? C6 C7 1.389(6) ? C7 C8 1.386(6) ? C8 C9 1.498(6) ? C10 C11 1.308(7) ? C10 H10 0.9300 ? C11 C12 1.479(7) ? C11 H11 0.9300 ? C12 C13A 1.519(8) y C12 C13B 1.495(8) y C12 H12A 0.9700 ? C12 H12B 0.9700 ? C12 H12C 0.9700 ? C12 H12D 0.9700 ? C13A C14 1.441(8) y C13A H13A 0.9700 ? C13A H13B 0.9700 ? C13B C14 1.449(8) y C13B H13C 0.9700 ? C13B H13D 0.9700 ? C14 H14A 0.9700 ? C14 H14B 0.9700 ? C14 H14C 0.9700 ? C14 H14D 0.9700 ? 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 C10 C1 C9 112.0(4) y C10 C1 C14 112.4(4) y C9 C1 C14 108.0(4) y C10 C1 C2 112.7(4) y C9 C1 C2 102.8(3) y C14 C1 C2 108.4(4) y O1 C2 C3 127.4(5) ? O1 C2 C1 124.4(4) ? C3 C2 C1 108.2(4) ? C8 C3 C4 120.5(4) ? C8 C3 C2 110.3(4) ? C4 C3 C2 129.1(4) ? C3 C4 C5 119.1(4) ? C3 C4 Cl4 121.2(4) ? C5 C4 Cl4 119.8(4) ? C6 C5 C4 119.8(4) ? C6 C5 Cl3 120.4(4) ? C4 C5 Cl3 119.8(4) ? C5 C6 C7 121.2(4) ? C5 C6 Cl2 119.5(4) ? C7 C6 Cl2 119.3(4) ? C8 C7 C6 118.1(4) ? C8 C7 Cl1 121.1(3) ? C6 C7 Cl1 120.8(4) ? C3 C8 C7 121.3(4) ? C3 C8 C9 109.2(4) ? C7 C8 C9 129.4(4) ? O2 C9 C8 125.8(4) ? O2 C9 C1 126.2(4) ? C8 C9 C1 108.1(4) ? C11 C10 C1 122.6(4) ? C11 C10 H10 118.7 ? C1 C10 H10 118.7 ? C10 C11 C12 125.2(5) ? C10 C11 H11 117.4 ? C12 C11 H11 117.4 ? C11 C12 C13A 110.8(6) ? C11 C12 C13B 111.0(6) ? C11 C12 H12A 109.5 ? C13A C12 H12A 109.5 ? C11 C12 H12B 109.5 ? C13A C12 H12B 109.5 ? H12A C12 H12B 108.1 ? C11 C12 H12C 109.4 ? C13B C12 H12C 109.4 ? C11 C12 H12D 109.4 ? C13B C12 H12D 109.4 ? H12C C12 H12D 108.0 ? C14 C13A C12 114.8(7) y C14 C13A H13A 108.6 ? C12 C13A H13A 108.6 ? C14 C13A H13B 108.6 ? C12 C13A H13B 108.6 ? H13A C13A H13B 107.5 ? C14 C13B C12 115.8(7) y C14 C13B H13C 108.3 ? C12 C13B H13C 108.3 ? C14 C13B H13D 108.3 ? C12 C13B H13D 108.3 ? H13C C13B H13D 107.4 ? C13A C14 C1 115.1(6) y C13B C14 C1 119.3(6) y C13A C14 H14A 108.5 ? C1 C14 H14A 108.5 ? C13A C14 H14B 108.5 ? C1 C14 H14B 108.5 ? H14A C14 H14B 107.5 ? C13B C14 H14C 107.5 ? C1 C14 H14C 107.5 ? C13B C14 H14D 107.5 ? C1 C14 H14D 107.5 ? H14C C14 H14D 107.0 ? 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 _geom_torsion_publ_flag C9 C1 C2 C3 -10.3(4) y C1 C2 C3 C8 5.1(4) y C2 C3 C8 C9 2.8(5) y C3 C8 C9 C1 -9.6(5) y C8 C9 C1 C2 11.9(4) y C14 C1 C10 C11 -4.3(7) y C1 C10 C11 C12 -2.4(9) y C10 C11 C12 C13A -16.1(9) y C10 C11 C12 C13B 25.4(9) y C11 C12 C13A C14 42.8(11) ? C11 C12 C13B C14 -42.1(12) ? C12 C13A C14 C1 -51.8(11) ? C12 C13B C14 C1 38.6(14) ? C13A C14 C1 C10 31.2(8) y C13B C14 C1 C10 -14.3(9) y _cod_database_code 2206017