#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010159.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_2010159 loop_ _publ_author_name 'Lynch, V. M.' 'Baran Jr, J. R.' 'Lagow, R. J.' 'Davis, Brian E.' _publ_section_title ; Three polyhalogenated tricyclo[5.1.0.0^3,5^]octane compounds ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1765 _journal_page_last 1768 _journal_paper_doi 10.1107/S0108270194003513 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C12 H16 Cl4' _chemical_formula_sum 'C12 H16 Cl4' _chemical_formula_weight 302.07 _chemical_name_systematic ; 4,4,8,8-tetrachloro-1,3,5,7-tetramethyl-cis-transoid-cis- tricyclo[5.1.0.0^3,5^]octane ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 100.33(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.436(4) _cell_length_b 6.954(3) _cell_length_c 14.850(9) _cell_measurement_reflns_used 16 _cell_measurement_temperature 193 _cell_measurement_theta_max 10.1 _cell_measurement_theta_min 6.3 _cell_volume 653.9(6) _computing_cell_refinement 'Siemens P3/V Data Collection Software, version 4.1' _computing_data_collection 'Siemens P3/V Data Collection Software, version 4.1' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1991)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material 'FUER (Larson, 1982); MPLN (Cordes, 1982)' _computing_structure_refinement SHELXTL-Plus _computing_structure_solution SHELXTL-Plus _diffrn_ambient_temperature 193.0(10) _diffrn_measurement_device 'Nicolet R3 diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2446 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 2 _diffrn_standards_decay_% 1.3 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.8806 _exptl_absorpt_correction_T_max 1.37 _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_type refdelf _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.53 _exptl_crystal_description plate _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.33 _refine_diff_density_min -0.17 _refine_ls_extinction_coef 6.2(2)E-5 _refine_ls_extinction_method 'modified Larson (Larson, 1982); SHELXTL-Plus (Sheldrick, 1991)' _refine_ls_goodness_of_fit_obs 1.361 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 106 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_obs 0.0243 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.0004F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0345 _refine_ls_wR_factor_obs 0.0333 _reflns_number_observed 1058 _reflns_number_total 1164 _reflns_observed_criterion F>4.0\s(F) _cod_data_source_file cr1110.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F)+0.0004F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F)+0.0004F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2010159 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 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 0.0340(3) 0.0272(3) 0.0276(3) -0.0022(2) 0.0072(2) 0.0086(2) Cl2 0.0350(3) 0.0270(3) 0.0428(3) -0.0071(2) -0.0068(2) -0.0081(2) C1 0.0250(8) 0.0193(7) 0.0210(8) -0.0030(6) 0.0000(6) 0.0000(6) C2 0.0243(8) 0.0191(7) 0.0178(7) 0.0001(6) 0.0029(6) -0.0013(6) C3 0.0210(8) 0.0204(8) 0.0223(8) 0.0019(6) 0.0038(6) 0.0007(6) C4 0.0224(7) 0.0189(7) 0.0184(8) 0.0005(5) 0.0016(5) 0.0012(6) C5 0.0378(10) 0.0332(10) 0.0204(9) 0.0035(8) 0.0067(7) -0.0038(7) C6 0.0299(9) 0.0294(9) 0.0220(8) 0.0036(7) -0.0018(7) 0.0027(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_calc_attached_atom Cl1 0.32561(6) 0.19240(6) 0.06276(3) 0.0294(2) uani ? Cl2 0.14379(7) 0.11237(6) -0.12506(3) 0.0366(2) uani ? C1 0.3062(2) 0.2716(2) -0.05125(10) 0.0223(4) uani ? C2 0.4956(2) 0.3634(2) -0.08022(10) 0.0205(4) uani ? C3 0.6954(2) 0.3786(2) -0.00859(11) 0.0212(5) uani ? C4 0.3002(2) 0.4847(2) -0.07138(10) 0.0201(4) uani ? C5 0.5435(3) 0.3178(3) -0.17398(12) 0.0303(6) uani ? C6 0.1584(3) 0.5568(3) -0.15708(11) 0.0279(5) uani ? H3A 0.724(3) 0.258(3) 0.0171(12) 0.023(4) uiso ? H3B 0.809(3) 0.417(3) -0.0405(13) 0.026(4) uiso ? H5A 0.628(3) 0.215(3) -0.1717(14) 0.040(6) uiso ? H5B 0.422(4) 0.288(3) -0.218(2) 0.048(6) uiso ? H5C 0.607(3) 0.424(3) -0.1961(14) 0.039(5) uiso ? H6A 0.211(3) 0.668(3) -0.182(2) 0.044(6) uiso ? H6B 0.137(3) 0.471(3) -0.202(2) 0.048(6) uiso ? H6C 0.030(4) 0.596(3) -0.1417(15) 0.042(6) uiso ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 'International Tables Vol.IV' Cl .132 .159 'International Tables Vol.IV' H 0 0 'International Tables Vol.IV' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -3 -3 -1 3 3 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 _geom_angle_publ_flag C2 C1 C4 . 61.36(10) yes C2 C1 Cl1 . 119.01(11) yes C2 C1 Cl2 . 120.57(12) yes C4 C1 Cl1 . 119.42(11) yes C4 C1 Cl2 . 120.13(10) yes Cl1 C1 Cl2 . 109.44(9) yes C3 C2 C4 . 120.27(13) yes C3 C2 C5 . 111.88(14) yes C3 C2 C1 . 117.19(13) yes C4 C2 C5 . 119.85(13) yes C4 C2 C1 . 59.49(10) yes C5 C2 C1 . 118.90(13) yes C6 C4 C1 . 118.78(12) yes C6 C4 C2 . 119.28(14) yes C1 C4 C2 . 59.14(10) yes C4 C3 C2 2_665 119.11(13) yes C3 C4 C6 2_665 112.00(13) yes C3 C4 C1 2_665 117.59(13) yes C3 C4 C2 2_665 120.62(12) yes H3A C3 H3B . 109(2) no H3A C3 C2 . 107.9(10) no H3B C3 C2 . 107.0(10) no H5A C5 H5B . 106(2) no H5A C5 H5C . 110(2) no H5A C5 C2 . 110.8(14) no H5B C5 H5C . 107(2) no H5B C5 C2 . 113(2) no H5C C5 C2 . 109.4(14) no H6A C6 H6B . 106(2) no H6A C6 H6C . 104(2) no H6A C6 C4 . 113.4(12) no H6B C6 H6C . 111(2) no H6B C6 C4 . 113.2(15) no H6C C6 C4 . 108.5(13) no C4 C3 H3A 2_665 105.7(11) no C4 C3 H3B 2_665 107.4(10) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 Cl1 . . 1.763(2) yes C1 Cl2 . . 1.763(2) yes C2 C1 . . 1.506(2) yes C4 C1 . . 1.511(2) yes C3 C2 . . 1.519(2) yes C4 C2 . . 1.539(2) yes C5 C2 . . 1.513(3) yes C6 C4 . . 1.513(2) yes C4 C3 . 2_665 1.517(2) yes H3A C3 . . 0.93(2) no H3B C3 . . 0.98(2) no H5A C5 . . 0.89(2) no H5B C5 . . 0.94(2) no H5C C5 . . 0.93(2) no H6A C6 . . 0.94(2) no H6B C6 . . 0.88(2) no H6C C6 . . 0.93(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139057359