#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012850.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_2012850 loop_ _publ_author_name 'Linden, Anthony' 'Majchrzak, Agnieszka' 'Cavegn, Jovita' 'Mloston, Grzegorz' 'Heimgartner, Heinz' _publ_section_title ; Four bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)oligosulfanes ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o480 _journal_page_last o484 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C16 H24 Cl2 O2 S2' _chemical_formula_sum 'C16 H24 Cl2 O2 S2' _chemical_formula_weight 383.39 _chemical_melting_point .371E-305 _chemical_name_systematic ; bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)disulfane ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 105.4292(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.73790(10) _cell_length_b 26.7454(4) _cell_length_c 10.6473(2) _cell_measurement_reflns_used 103426 _cell_measurement_temperature 160.0(10) _cell_measurement_theta_max 30.0 _cell_measurement_theta_min 2.0 _cell_volume 1849.58(5) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2002)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 160.0(10) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'Nonius FR591 sealed tube generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_sigmaI/netI 0.047 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 40268 _diffrn_reflns_theta_full 30.01 _diffrn_reflns_theta_max 30.01 _diffrn_reflns_theta_min 3.03 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.580 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(Coppens et al., 1965)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.37 _refine_diff_density_min -0.35 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 5397 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.5066P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.082 _refine_ls_wR_factor_ref 0.093 _reflns_number_gt 3839 _reflns_number_total 5400 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1503.cif _[local]_cod_data_source_block III _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2012850 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 1.10057(7) 0.069552(19) 0.59120(4) 0.03346(12) Uani d . 1 . . Cl Cl2 0.78806(6) 0.192378(16) 0.41231(4) 0.02775(11) Uani d . 1 . . Cl S1 0.64412(6) 0.072255(16) 0.52548(4) 0.02409(10) Uani d . 1 . . S S2 0.69317(7) 0.086746(16) 0.34955(4) 0.02372(10) Uani d . 1 . . S O1 1.0234(2) 0.09743(5) 0.97583(12) 0.0380(3) Uani d . 1 . . O O2 0.2449(2) 0.21167(5) 0.09187(13) 0.0371(3) Uani d . 1 . . O C1 0.8859(2) 0.08087(6) 0.65477(15) 0.0218(3) Uani d . 1 . . C C2 0.8876(3) 0.04590(6) 0.77643(16) 0.0241(4) Uani d . 1 . . C C3 0.9560(3) 0.09207(7) 0.86002(16) 0.0254(4) Uani d . 1 . . C C4 0.9163(3) 0.12886(7) 0.74607(16) 0.0256(4) Uani d . 1 . . C C5 1.0378(3) 0.00234(7) 0.80294(19) 0.0363(4) Uani d . 1 . . C H51 1.1782 0.0149 0.8150 0.054 Uiso calc R 1 . . H H52 1.0038 -0.0208 0.7290 0.054 Uiso calc R 1 . . H H53 1.0282 -0.0152 0.8820 0.054 Uiso calc R 1 . . H C6 0.6747(3) 0.02806(7) 0.78537(18) 0.0320(4) Uani d . 1 . . C H61 0.6266 0.0009 0.7229 0.048 Uiso calc R 1 . . H H62 0.5770 0.0560 0.7652 0.048 Uiso calc R 1 . . H H63 0.6849 0.0160 0.8737 0.048 Uiso calc R 1 . . H C7 1.0954(3) 0.16412(8) 0.74896(19) 0.0377(5) Uani d . 1 . . C H71 1.1140 0.1870 0.8231 0.057 Uiso calc R 1 . . H H72 1.0659 0.1834 0.6678 0.057 Uiso calc R 1 . . H H73 1.2215 0.1446 0.7578 0.057 Uiso calc R 1 . . H C8 0.7192(3) 0.15920(7) 0.73639(18) 0.0333(4) Uani d . 1 . . C H81 0.7369 0.1798 0.8146 0.050 Uiso calc R 1 . . H H82 0.6030 0.1363 0.7291 0.050 Uiso calc R 1 . . H H83 0.6919 0.1808 0.6593 0.050 Uiso calc R 1 . . H C9 0.6083(2) 0.15057(6) 0.30954(15) 0.0213(3) Uani d . 1 . . C C10 0.5727(3) 0.16323(6) 0.15825(16) 0.0245(4) Uani d . 1 . . C C11 0.3665(3) 0.18532(6) 0.16538(17) 0.0251(4) Uani d . 1 . . C C12 0.3766(2) 0.16529(6) 0.30114(16) 0.0227(3) Uani d . 1 . . C C13 0.7134(3) 0.20109(7) 0.11823(19) 0.0341(4) Uani d . 1 . . C H131 0.6476 0.2134 0.0303 0.051 Uiso calc R 1 . . H H132 0.8445 0.1851 0.1191 0.051 Uiso calc R 1 . . H H133 0.7385 0.2292 0.1795 0.051 Uiso calc R 1 . . H C14 0.5470(3) 0.11729(7) 0.06844(17) 0.0324(4) Uani d . 1 . . C H141 0.4941 0.1279 -0.0224 0.049 Uiso calc R 1 . . H H142 0.4500 0.0938 0.0907 0.049 Uiso calc R 1 . . H H143 0.6807 0.1009 0.0798 0.049 Uiso calc R 1 . . H C15 0.3348(3) 0.20333(7) 0.39731(19) 0.0317(4) Uani d . 1 . . C H151 0.4348 0.2307 0.4082 0.047 Uiso calc R 1 . . H H152 0.3473 0.1871 0.4816 0.047 Uiso calc R 1 . . H H153 0.1953 0.2167 0.3641 0.047 Uiso calc R 1 . . H C16 0.2302(3) 0.12054(7) 0.29045(17) 0.0273(4) Uani d . 1 . . C H161 0.2555 0.1040 0.3754 0.041 Uiso calc R 1 . . H H162 0.2544 0.0968 0.2260 0.041 Uiso calc R 1 . . H H163 0.0874 0.1323 0.2632 0.041 Uiso calc R 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 0.0254(2) 0.0520(3) 0.0250(2) 0.00527(19) 0.01036(17) 0.0035(2) Cl2 0.0264(2) 0.0298(2) 0.0268(2) -0.00458(17) 0.00671(17) -0.00365(17) S1 0.0246(2) 0.0278(2) 0.01853(19) -0.00379(17) 0.00350(16) 0.00245(16) S2 0.0299(2) 0.0238(2) 0.01701(19) 0.00530(17) 0.00555(16) -0.00017(16) O1 0.0497(8) 0.0422(8) 0.0185(6) -0.0082(7) 0.0027(6) 0.0005(6) O2 0.0336(7) 0.0415(8) 0.0357(8) 0.0103(6) 0.0081(6) 0.0168(6) C1 0.0203(8) 0.0269(9) 0.0174(7) 0.0011(6) 0.0038(6) 0.0015(6) C2 0.0283(9) 0.0249(9) 0.0192(8) 0.0012(7) 0.0063(7) 0.0042(7) C3 0.0245(8) 0.0323(10) 0.0194(8) -0.0015(7) 0.0058(7) 0.0019(7) C4 0.0303(9) 0.0266(9) 0.0184(8) -0.0050(7) 0.0038(7) 0.0009(7) C5 0.0449(12) 0.0329(10) 0.0306(10) 0.0089(9) 0.0093(9) 0.0077(8) C6 0.0360(10) 0.0347(10) 0.0256(9) -0.0076(8) 0.0088(8) 0.0066(8) C7 0.0435(11) 0.0377(11) 0.0280(10) -0.0156(9) 0.0027(9) 0.0023(8) C8 0.0451(11) 0.0270(10) 0.0284(10) 0.0047(8) 0.0106(8) -0.0026(8) C9 0.0223(8) 0.0219(8) 0.0197(8) 0.0005(6) 0.0057(6) 0.0007(6) C10 0.0261(8) 0.0292(9) 0.0196(8) 0.0038(7) 0.0085(7) 0.0043(7) C11 0.0250(8) 0.0261(9) 0.0240(8) 0.0005(7) 0.0063(7) 0.0026(7) C12 0.0214(8) 0.0245(9) 0.0227(8) 0.0035(6) 0.0070(6) 0.0027(7) C13 0.0346(10) 0.0407(11) 0.0311(10) 0.0020(8) 0.0156(8) 0.0118(8) C14 0.0390(10) 0.0397(11) 0.0183(8) 0.0057(9) 0.0073(7) 0.0001(8) C15 0.0298(9) 0.0330(10) 0.0351(10) 0.0058(8) 0.0139(8) -0.0034(8) C16 0.0232(8) 0.0332(10) 0.0246(9) -0.0033(7) 0.0047(7) 0.0036(7) 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 . 1.7786(17) yes Cl2 C9 . 1.7915(17) yes S1 C1 . 1.8462(16) yes S1 S2 . 2.0243(6) yes S2 C9 . 1.8146(17) yes O1 C3 . 1.204(2) ? O2 C11 . 1.200(2) ? C1 C2 . 1.595(2) yes C1 C4 . 1.590(2) yes C2 C5 . 1.519(2) ? C2 C3 . 1.520(2) ? C2 C6 . 1.539(2) ? C3 C4 . 1.529(2) ? C4 C7 . 1.526(3) ? C4 C8 . 1.536(3) ? C5 H51 . 0.9800 ? C5 H52 . 0.9800 ? C5 H53 . 0.9800 ? C6 H61 . 0.9800 ? C6 H62 . 0.9800 ? C6 H63 . 0.9800 ? C7 H71 . 0.9800 ? C7 H72 . 0.9800 ? C7 H73 . 0.9800 ? C8 H81 . 0.9800 ? C8 H82 . 0.9800 ? C8 H83 . 0.9800 ? C9 C10 . 1.601(2) yes C9 C12 . 1.589(2) yes C10 C13 . 1.523(2) ? C10 C11 . 1.530(2) ? C10 C14 . 1.538(2) ? C11 C12 . 1.526(2) ? C12 C15 . 1.522(2) ? C12 C16 . 1.536(2) ? C13 H131 . 0.9800 ? C13 H132 . 0.9800 ? C13 H133 . 0.9800 ? C14 H141 . 0.9800 ? C14 H142 . 0.9800 ? C14 H143 . 0.9800 ? C15 H151 . 0.9800 ? C15 H152 . 0.9800 ? C15 H153 . 0.9800 ? C16 H161 . 0.9800 ? C16 H162 . 0.9800 ? C16 H163 . 0.9800 ? 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 for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992). 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 C1 S1 S2 109.71(6) yes C9 S2 S1 106.17(6) yes C2 C1 C4 90.28(12) yes C4 C1 Cl1 112.62(11) ? C2 C1 Cl1 112.22(11) ? C4 C1 S1 120.07(11) ? C2 C1 S1 110.29(11) ? Cl1 C1 S1 109.91(8) ? C5 C2 C3 115.52(15) ? C5 C2 C6 109.66(15) ? C3 C2 C6 110.98(14) ? C5 C2 C1 117.46(14) ? C1 C2 C3 86.26(12) yes C6 C2 C1 115.24(14) ? O1 C3 C2 132.01(16) ? O1 C3 C4 132.43(17) ? C2 C3 C4 95.53(13) yes C7 C4 C3 114.26(15) ? C7 C4 C8 109.89(16) ? C3 C4 C8 111.04(14) ? C7 C4 C1 118.92(15) ? C1 C4 C3 86.12(12) yes C8 C4 C1 114.65(14) ? C2 C5 H51 109.5 ? C2 C5 H52 109.5 ? H51 C5 H52 109.5 ? C2 C5 H53 109.5 ? H51 C5 H53 109.5 ? H52 C5 H53 109.5 ? C2 C6 H61 109.5 ? C2 C6 H62 109.5 ? H61 C6 H62 109.5 ? C2 C6 H63 109.5 ? H61 C6 H63 109.5 ? H62 C6 H63 109.5 ? C4 C7 H71 109.5 ? C4 C7 H72 109.5 ? H71 C7 H72 109.5 ? C4 C7 H73 109.5 ? H71 C7 H73 109.5 ? H72 C7 H73 109.5 ? C4 C8 H81 109.5 ? C4 C8 H82 109.5 ? H81 C8 H82 109.5 ? C4 C8 H83 109.5 ? H81 C8 H83 109.5 ? H82 C8 H83 109.5 ? C10 C9 C12 90.52(12) yes C12 C9 Cl2 111.97(11) ? C10 C9 Cl2 112.25(11) ? C12 C9 S2 119.33(11) ? C10 C9 S2 112.87(11) ? Cl2 C9 S2 108.91(8) ? C13 C10 C11 113.45(14) ? C13 C10 C14 109.43(14) ? C11 C10 C14 112.69(15) ? C13 C10 C9 118.97(15) ? C9 C10 C11 85.79(12) yes C14 C10 C9 114.76(14) ? O2 C11 C12 132.43(16) ? O2 C11 C10 131.76(16) ? C10 C11 C12 95.69(13) yes C15 C12 C11 115.66(14) ? C15 C12 C16 109.92(14) ? C11 C12 C16 109.72(14) ? C15 C12 C9 118.86(14) ? C9 C12 C11 86.33(12) yes C16 C12 C9 114.39(14) ? C10 C13 H131 109.5 ? C10 C13 H132 109.5 ? H131 C13 H132 109.5 ? C10 C13 H133 109.5 ? H131 C13 H133 109.5 ? H132 C13 H133 109.5 ? C10 C14 H141 109.5 ? C10 C14 H142 109.5 ? H141 C14 H142 109.5 ? C10 C14 H143 109.5 ? H141 C14 H143 109.5 ? H142 C14 H143 109.5 ? C12 C15 H151 109.5 ? C12 C15 H152 109.5 ? H151 C15 H152 109.5 ? C12 C15 H153 109.5 ? H151 C15 H153 109.5 ? H152 C15 H153 109.5 ? C12 C16 H161 109.5 ? C12 C16 H162 109.5 ? H161 C16 H162 109.5 ? C12 C16 H163 109.5 ? H161 C16 H163 109.5 ? H162 C16 H163 109.5 ? 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 S1 S2 C9 -97.90(8) yes S2 S1 C1 C4 105.37(12) ? S2 S1 C1 C2 -151.91(9) ? S2 S1 C1 Cl1 -27.65(10) ? C4 C1 C2 C5 -126.84(16) ? Cl1 C1 C2 C5 -12.17(19) ? S1 C1 C2 C5 110.74(15) ? C4 C1 C2 C3 -9.93(12) ? Cl1 C1 C2 C3 104.74(12) ? S1 C1 C2 C3 -132.34(11) ? C4 C1 C2 C6 101.53(16) ? Cl1 C1 C2 C6 -143.80(13) ? S1 C1 C2 C6 -20.88(18) ? C5 C2 C3 O1 -49.2(3) ? C6 C2 C3 O1 76.4(2) ? C1 C2 C3 O1 -167.9(2) ? C5 C2 C3 C4 129.12(15) ? C6 C2 C3 C4 -105.26(15) ? C1 C2 C3 C4 10.38(13) ? O1 C3 C4 C7 47.8(3) ? C2 C3 C4 C7 -130.49(16) ? O1 C3 C4 C8 -77.2(2) ? C2 C3 C4 C8 104.53(15) ? O1 C3 C4 C1 167.9(2) ? C2 C3 C4 C1 -10.41(13) ? C2 C1 C4 C7 125.53(16) ? Cl1 C1 C4 C7 11.22(19) ? S1 C1 C4 C7 -120.66(15) ? C2 C1 C4 C3 9.87(12) ? Cl1 C1 C4 C3 -104.44(12) ? S1 C1 C4 C3 123.68(13) ? C2 C1 C4 C8 -101.52(15) ? Cl1 C1 C4 C8 144.16(13) ? S1 C1 C4 C8 12.3(2) ? S1 S2 C9 C12 -58.57(13) ? S1 S2 C9 C10 -162.95(10) ? S1 S2 C9 Cl2 71.68(8) ? C12 C9 C10 C13 124.07(16) ? Cl2 C9 C10 C13 9.99(19) ? S2 C9 C10 C13 -113.56(15) ? C12 C9 C10 C11 9.53(12) ? Cl2 C9 C10 C11 -104.55(12) ? S2 C9 C10 C11 131.90(12) ? C12 C9 C10 C14 -103.55(15) ? Cl2 C9 C10 C14 142.38(13) ? S2 C9 C10 C14 18.82(18) ? C13 C10 C11 O2 46.6(3) ? C14 C10 C11 O2 -78.5(2) ? C9 C10 C11 O2 166.4(2) ? C13 C10 C11 C12 -129.82(15) ? C14 C10 C11 C12 105.13(15) ? C9 C10 C11 C12 -9.98(13) ? O2 C11 C12 C15 -45.9(3) ? C10 C11 C12 C15 130.42(15) ? O2 C11 C12 C16 79.1(2) ? C10 C11 C12 C16 -104.57(15) ? O2 C11 C12 C9 -166.3(2) ? C10 C11 C12 C9 10.04(13) ? C10 C9 C12 C15 -126.95(16) ? Cl2 C9 C12 C15 -12.62(19) ? S2 C9 C12 C15 116.25(15) ? C10 C9 C12 C11 -9.55(12) ? Cl2 C9 C12 C11 104.77(12) ? S2 C9 C12 C11 -126.36(12) ? C10 C9 C12 C16 100.45(15) ? Cl2 C9 C12 C16 -145.22(12) ? S2 C9 C12 C16 -16.35(19) ?