#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006889.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_2006889 loop_ _publ_author_name 'Mackay, M. F.' 'Banwell, M. G.' 'Pallich, S.' 'Phyland, J. R.' _publ_section_title ; Novel Products from the Rearrangement of Some [n.3.1]Propellanes ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2000 _journal_page_last 2002 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C12 H13 Cl3 O' _chemical_formula_structural 'C12 H13 Cl3 O' _chemical_formula_sum 'C12 H13 Cl3 O' _chemical_formula_weight 279.59 _chemical_melting_point 324.5(5) _chemical_name_systematic ; (3a\a,6\a)-(E)-5-Chloromethylene-8,8-dichloro-6-methoxy-1,2,3,4,5,6-hexahydro- 3a\,6-methanO-3aH-indene ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method 'SHELXL-93 ( Sheldrick,1993)' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.818(2) _cell_length_b 11.1910(10) _cell_length_c 11.7900(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 18 _cell_measurement_theta_min 17 _cell_volume 1295.4(3) _computing_cell_refinement 'Rigaku AFC software' _computing_data_collection 'Rigaku AFC software' _computing_data_reduction 'Rigaku AFC software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 292(2) _diffrn_measurement_device 'Rigaku AFC' _diffrn_measurement_method w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0 _diffrn_reflns_av_sigmaI/netI 0.0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1084 _diffrn_reflns_theta_max 65.0 _diffrn_reflns_theta_min 5.5 _diffrn_standards_decay_% <4.5 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 6.21 _exptl_absorpt_correction_T_max 0.327 _exptl_absorpt_correction_T_min 0.184 _exptl_absorpt_correction_type 'Gaussian (SHELX76: Sheldrick, 1976)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 576.0 _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.308 _exptl_crystal_size_min 0.256 _refine_diff_density_max 0.190 _refine_diff_density_min -0.189 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.15(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.109 _refine_ls_goodness_of_fit_obs 1.109 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 159 _refine_ls_number_reflns 1084 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.109 _refine_ls_restrained_S_obs 1.109 _refine_ls_R_factor_all 0.039 _refine_ls_R_factor_obs 0.037 _refine_ls_shift/esd_max 0.017 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.1681P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 1.107 _refine_ls_wR_factor_obs 1.107 _reflns_number_observed 1026 _reflns_number_total 1084 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file ta1168.cif _[local]_cod_data_source_block 4 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '324-325' was changed to '324.5(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 ; _cod_database_code 2006889 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 C1 0.148(7) 0.059(3) 0.065(4) -0.034(4) -0.009(5) -0.015(3) C2 0.119(6) 0.075(4) 0.257(16) -0.051(5) 0.093(8) -0.029(7) C3 0.064(4) 0.083(4) 0.104(5) -0.023(3) 0.021(4) -0.003(4) C3a 0.054(2) 0.042(2) 0.061(3) -0.002(2) 0.021(2) -0.004(2) C4 0.056(3) 0.062(3) 0.057(3) 0.005(2) -0.003(3) 0.001(2) C5 0.052(2) 0.047(2) 0.036(2) 0.010(2) 0.000(2) -0.002(2) C5' 0.077(4) 0.055(3) 0.062(3) 0.014(3) 0.035(3) 0.009(2) Cl5 0.154(2) 0.0746(9) 0.0491(7) 0.0135(11) -0.0041(9) 0.0194(6) C6 0.041(2) 0.054(2) 0.044(2) 0.002(2) 0.001(2) 0.007(2) O6 0.047(2) 0.098(3) 0.078(3) 0.004(2) -0.014(2) 0.018(2) C6' 0.042(3) 0.111(5) 0.091(5) 0.012(3) -0.027(3) 0.012(4) C7a 0.062(3) 0.043(2) 0.039(2) 0.002(2) 0.013(2) 0.001(2) C7 0.072(3) 0.042(2) 0.051(3) 0.015(2) 0.002(3) 0.000(2) C8 0.063(3) 0.035(2) 0.039(2) -0.003(2) 0.009(2) 0.000(2) Cl8 0.1276(13) 0.0819(9) 0.0438(6) -0.0211(9) -0.0051(8) 0.0082(6) Cl8' 0.1114(11) 0.0475(6) 0.0763(8) -0.0179(7) 0.0260(9) -0.0151(6) 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 C1 0.1395(9) 0.4287(5) 0.7872(6) 0.091(2) Uani d . 1 C H1a 0.1753 0.3559 0.8204 0.15(4) Uiso calc R 1 H H1b 0.0956 0.4097 0.7157 0.11(3) Uiso calc R 1 H C2 0.0387(10) 0.4925(7) 0.8698(14) 0.150(5) Uani d . 1 C H2a -0.0542 0.4700 0.8520 0.08(2) Uiso calc R 1 H H2b 0.0578 0.4689 0.9474 0.21(7) Uiso calc R 1 H C3 0.0559(6) 0.6246(6) 0.8573(7) 0.084(2) Uani d . 1 C H3a 0.0552 0.6632 0.9310 0.11(3) Uiso calc R 1 H H3b -0.0170 0.6579 0.8116 0.07(2) Uiso calc R 1 H C3a 0.1926(5) 0.6422(4) 0.7992(5) 0.0524(11) Uani d . 1 C C4 0.1943(5) 0.7114(5) 0.6828(5) 0.0585(12) Uani d . 1 C H4a 0.1490 0.6661 0.6237 0.13(3) Uiso calc R 1 H H4b 0.1514 0.7892 0.6896 0.09(2) Uiso calc R 1 H C5 0.3424(5) 0.7228(4) 0.6599(4) 0.0448(10) Uani d . 1 C C5' 0.4063(6) 0.7794(5) 0.5734(4) 0.0649(15) Uani d . 1 C H5' 0.5009 0.7779 0.5696 0.068(17) Uiso calc R 1 H Cl5 0.3169(2) 0.85308(13) 0.47152(11) 0.0925(6) Uani d . 1 Cl C6 0.4164(4) 0.6590(4) 0.7536(4) 0.0463(10) Uani d . 1 C O6 0.5522(3) 0.6901(4) 0.7589(4) 0.0742(11) Uani d . 1 O C6' 0.6426(6) 0.6230(7) 0.8253(7) 0.081(2) Uani d . 1 C H6a 0.7324 0.6565 0.8197 0.10(2) Uiso calc R 1 H H6b 0.6440 0.5419 0.7988 0.10(3) Uiso calc R 1 H H6g 0.6134 0.6246 0.9030 0.40(14) Uiso calc R 1 H C7a 0.2474(5) 0.5181(4) 0.7715(4) 0.0481(10) Uani d . 1 C C7 0.3781(6) 0.5254(4) 0.7448(4) 0.0548(12) Uani d . 1 C H7 0.4354 0.4626 0.7247 0.07(2) Uiso calc R 1 H C8 0.3201(5) 0.6934(4) 0.8572(4) 0.0457(10) Uani d . 1 C Cl8 0.3563(2) 0.62452(13) 0.98790(11) 0.0844(5) Uani d . 1 Cl Cl8' 0.3134(2) 0.85072(11) 0.88086(13) 0.0784(5) Uani d . 1 Cl loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' 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 C2 C1 C7a 103.0(4) yes C1 C2 C3 108.6(7) yes C2 C3 C3a 105.8(6) yes C3 C3a C4 117.8(5) yes C3 C3a C7a 106.8(4) yes C3 C3a C8 124.5(5) yes C4 C3a C7a 105.0(4) yes C4 C3a C8 101.3(3) yes C7a C3a C8 98.5(4) yes C3a C4 C5 102.2(4) yes C4 C5 C5' 129.1(5) yes C4 C5 C6 107.4(4) yes C5' C5 C6 123.5(4) yes C5 C5' Cl5 121.3(4) yes C5 C6 O6 112.4(4) yes C5 C6 C7 107.1(4) yes C5 C6 C8 99.3(3) yes O6 C6 C7 118.8(4) yes O6 C6 C8 118.5(4) yes C7 C6 C8 98.1(3) yes C6 O6 C6' 120.2(5) yes C6 C7 C7a 106.2(4) yes C1 C7a C7 140.5(5) yes C1 C7a C3a 109.8(5) yes C3a C7a C7 109.7(4) yes C3a C8 C6 92.9(3) yes C3a C8 Cl8 113.0(3) yes C3a C8 Cl8' 114.0(3) yes C6 C8 Cl8 116.5(3) yes C6 C8 Cl8' 112.4(3) yes Cl8 C8 Cl8' 107.7(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.562(11) yes C1 C7a 1.468(8) yes C2 C3 1.495(10) yes C3 C3a 1.520(7) yes C3a C4 1.576(7) yes C3a C7a 1.525(6) yes C3a C8 1.538(7) yes C4 C5 1.484(7) yes C5 C5' 1.354(6) yes C5 C6 1.503(6) yes C5' Cl5 1.701(6) yes C6 O6 1.380(6) yes C6 C7 1.545(7) yes C6 C8 1.592(6) yes O6 C6' 1.402(7) yes C7 C7a 1.323(8) yes C8 Cl8 1.759(4) yes C8 Cl8' 1.783(4) yes 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 C1 C2 C3 C3a 17.8(12) yes C2 C3 C3a C7a -4.0(9) yes C3 C3a C7a C1 -12.2(6) yes C3a C7a C1 C2 22.2(9) yes C7a C1 C2 C3 -24.8(12) yes C3a C4 C5 C6 -2.7(5) yes C4 C5 C6 C7 -64.2(5) yes C5 C6 C7 C7a 67.9(5) yes C6 C7 C7a C3a 0.1(5) yes C7 C7a C3a C4 -68.4(5) yes C7a C3a C4 C5 67.5(5) yes C3a C4 C5 C5' 176.8(5) yes C4 C5 C5' Cl5 -1.0(8) yes C5' C5 C6 O6 -16.0(6) yes C5 C6 O6 C6' 167.3(5) yes C2 C3 C3a C8 109.3(9) yes C7 C7a C3a C8 35.8(5) yes C4 C5 C6 C8 37.3(4) yes C5 C6 C8 Cl8' 61.6(4) yes C7a C3a C8 Cl8 68.0(3) yes