#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:42:47 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248750 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557445.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557445 loop_ _publ_author_name 'Wang, Chengyuan' 'Hashizume, Daisuke' 'Nakano, Masahiro' 'Ogaki, Takuya' 'Takenaka, Hiroyuki' 'Kawabata, Kohsuke' 'Takimiya, Kazuo' _publ_section_title ; “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched \p-stacking ; _journal_issue 6 _journal_name_full 'Chemical Science' _journal_page_first 1573 _journal_paper_doi 10.1039/C9SC05902D _journal_volume 11 _journal_year 2020 _chemical_formula_moiety '2(C7 H4 S)' _chemical_formula_sum 'C14 H8 S2' _chemical_formula_weight 240.32 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2018-12-08 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-02-26 deposited with the CCDC. 2019-12-16 downloaded from the CCDC. ; _cell_angle_alpha 90.458(3) _cell_angle_beta 101.223(3) _cell_angle_gamma 93.037(3) _cell_formula_units_Z 2 _cell_length_a 5.8903(3) _cell_length_b 7.8065(4) _cell_length_c 11.6922(6) _cell_measurement_reflns_used 5776 _cell_measurement_temperature 223 _cell_measurement_theta_max 68.23 _cell_measurement_theta_min 3.86 _cell_volume 526.52(5) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku)' _computing_data_reduction 'RAPID AUTO' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 223.15 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID---RIKEN' _diffrn_measurement_method \w _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_unetI/netI 0.0752 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9414 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.687 _diffrn_reflns_theta_max 68.232 _diffrn_reflns_theta_min 3.855 _diffrn_source_target Cu _exptl_absorpt_coefficient_mu 4.256 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.500 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 147 _refine_ls_number_reflns 1881 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0689 _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^)+(0.1170P)^2^+0.1207P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1962 _refine_ls_wR_factor_ref 0.2081 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1374 _reflns_number_total 1881 _reflns_threshold_expression F^2^>2.0\s(F^2^) _iucr_refine_instructions_details ; TITL 181204-NDT shelxl.res created by SHELXL-2018/3 at 13:41:43 on 07-Dec-2018 CELL 1.54187 5.8903 7.80649 11.69216 90.4575 101.2226 93.0372 ZERR 2 0.00026 0.00038 0.0006 0.0033 0.003 0.0029 LATT 1 SFAC C H S UNIT 28 16 4 EADP C1A S2A EADP C1B S2B EXYZ C1A S2A EXYZ C1B S2B SUMP 1 0.000001 1 2 1 3 L.S. 5 PLAN 5 SIZE 0.6 0.4 0.01 TEMP -50 WPDB -2 HTAB BOND $H CONF LIST 4 fmap 2 acta OMIT 0 1 5 OMIT 1 3 0 OMIT -1 -3 5 OMIT -4 0 8 OMIT -1 -4 5 OMIT 4 3 1 OMIT -4 0 5 OMIT 1 5 6 OMIT 0 1 7 OMIT 0 1 8 OMIT 0 1 1 OMIT 4 -2 2 REM REM REM WGHT 0.117000 0.120700 FVAR 2.39713 0.76754 0.23246 S1 3 0.676617 1.073414 0.867728 11.00000 0.04480 0.05411 = 0.04553 0.00313 0.00454 0.00471 PART 1 C1A 1 -0.223568 0.551128 0.811026 21.00000 0.04012 0.05121 = 0.06335 0.00909 0.00526 0.00076 AFIX 43 H1A 2 -0.365217 0.505668 0.826544 21.00000 -1.20000 AFIX 0 S2B 3 0.182183 0.712786 0.841424 -31.00000 0.04528 0.05217 = 0.05609 -0.00646 0.00210 0.00134 PART 0 PART 2 S2A 3 -0.223568 0.551128 0.811026 -21.00000 0.04012 0.05121 = 0.06335 0.00909 0.00526 0.00076 C1B 1 0.182183 0.712786 0.841424 31.00000 0.04528 0.05217 = 0.05609 -0.00646 0.00210 0.00134 AFIX 43 H1B 2 0.316305 0.777015 0.878328 31.00000 -1.20000 AFIX 0 PART 0 C2 1 0.709741 0.975411 0.640941 11.00000 0.02688 0.03351 = 0.04538 0.00764 0.00394 0.00383 AFIX 43 H2 2 0.855602 0.931777 0.668656 11.00000 -1.20000 AFIX 0 C3 1 -0.226679 0.452434 0.589123 11.00000 0.02707 0.03085 = 0.05114 0.00320 0.00428 -0.00040 AFIX 43 H3 2 -0.372274 0.393514 0.581921 11.00000 -1.20000 AFIX 0 C4 1 0.212044 0.628080 0.612802 11.00000 0.02762 0.03451 = 0.05024 0.00291 0.00174 0.00302 AFIX 43 H4 2 0.358007 0.686888 0.621556 11.00000 -1.20000 AFIX 0 C5 1 0.276111 1.189787 0.775757 11.00000 0.02870 0.02739 = 0.04658 0.00203 0.00783 -0.00299 AFIX 43 H5 2 0.133278 1.240988 0.768730 11.00000 -1.20000 AFIX 0 C6 1 0.270629 1.108076 0.560336 11.00000 0.02717 0.02910 = 0.04801 0.00463 0.00485 0.00364 AFIX 43 H6 2 0.124236 1.151637 0.533943 11.00000 -1.20000 AFIX 0 C7 1 0.367084 1.117367 0.677351 11.00000 0.02737 0.03073 = 0.04909 0.00494 0.00962 0.00112 C8 1 0.612254 0.965908 0.521182 11.00000 0.02296 0.02608 = 0.04615 0.00561 0.00603 -0.00071 C9 1 -0.128028 0.534829 0.692386 11.00000 0.03080 0.03583 = 0.04939 0.00569 0.00581 0.00657 C10 1 0.112299 0.544996 0.506485 11.00000 0.02516 0.02716 = 0.04935 0.00317 0.00267 0.00190 C11 1 0.591602 1.048473 0.717254 11.00000 0.02928 0.03183 = 0.04059 0.00714 0.00428 0.00210 C12 1 0.095854 0.623222 0.703961 11.00000 0.02961 0.03166 = 0.05085 0.00307 0.00060 0.00163 C13 1 0.427503 1.171789 0.876947 11.00000 0.05480 0.04422 = 0.04873 -0.00255 0.01855 -0.00570 AFIX 43 H13 2 0.397922 1.211061 0.948551 11.00000 -1.20000 AFIX 0 C14 1 -0.054163 0.645387 0.884353 11.00000 0.08851 0.07873 = 0.04659 0.00384 0.01165 0.03761 PART 1 AFIX 43 H14 2 -0.073361 0.671913 0.960337 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H14A 2 -0.073361 0.671913 0.960337 -21.00000 -1.20000 AFIX 0 HKLF 4 REM 181204-NDT REM wR2 = 0.2081, GooF = S = 1.068, Restrained GooF = 1.067 for all data REM R1 = 0.0689 for 1374 Fo > 4sig(Fo) and 0.0856 for all 1881 data REM 147 parameters refined using 1 restraints END WGHT 0.1170 0.1208 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.500, deepest hole -0.366, 1-sigma level 0.090 Q1 1 0.1411 0.6699 0.7746 11.00000 0.05 0.50 Q2 1 0.6549 1.0784 0.7802 11.00000 0.05 0.48 Q3 1 0.4980 1.0823 0.8664 11.00000 0.05 0.44 Q4 1 0.2830 1.1840 0.7242 11.00000 0.05 0.38 Q5 1 0.3780 1.1687 0.7941 11.00000 0.05 0.37 REM The information below was added by Olex2. REM REM R1 = 0.0689 for 1374 Fo > 4sig(Fo) and 0.0856 for all 9500 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.50, deepest hole -0.37 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0856 REM R1_gt = 0.0689 REM wR_ref = 0.2081 REM GOOF = 1.068 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 9500 REM Reflections_gt = 1374 REM Parameters = n/a REM Hole = -0.37 REM Peak = 0.50 REM Flack = n/a ; _cod_data_source_file c9sc05902d2.cif _cod_data_source_block shelxl _cod_original_cell_volume 526.52(4) _cod_database_code 1557445 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.959 _shelx_estimated_absorpt_t_min 0.184 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Shared sites {C1A, S2A} {C1B, S2B} 3. Uiso/Uaniso restraints and constraints Uanis(C1A) = Uanis(S2A) Uanis(C1B) = Uanis(S2B) 4. Others 1*[Sof(C1A)+Sof(H1A)+Sof(S2A)+Sof(H14)+Sof(H14A)]+1*[Sof(S2B)+Sof(C1B)+ Sof(H1B)]=1 with esd of 0.000001 Sof(S2A)=Sof(H14A)=1-FVAR(1) Sof(C1A)=Sof(H1A)=Sof(H14)=FVAR(1) Sof(S2B)=1-FVAR(2) Sof(C1B)=Sof(H1B)=FVAR(2) 5.a Aromatic/amide H refined with riding coordinates: C1A(H1A), C1B(H1B), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C14(H14A) ; _diffractometer_make_and_type 'Rigaku R-AXIS RAPID' _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.67662(17) 1.07341(14) 0.86773(9) 0.0486(4) Uani 1 1 d . . . . . C1A C -0.2236(4) 0.5511(3) 0.8110(2) 0.0522(8) Uani 0.768(2) 1 d . . P A 1 H1A H -0.365217 0.505668 0.826544 0.063 Uiso 0.768(2) 1 calc R . P A 1 S2B S 0.1822(2) 0.71279(17) 0.84142(11) 0.0523(5) Uani 0.768(2) 1 d . . P A 1 S2A S -0.2236(4) 0.5511(3) 0.8110(2) 0.0522(8) Uani 0.232(2) 1 d . . P A 2 C1B C 0.1822(2) 0.71279(17) 0.84142(11) 0.0523(5) Uani 0.232(2) 1 d . . P A 2 H1B H 0.316305 0.777015 0.878328 0.063 Uiso 0.232(2) 1 calc R . P A 2 C2 C 0.7097(6) 0.9754(5) 0.6409(3) 0.0356(9) Uani 1 1 d . . . . . H2 H 0.855602 0.931777 0.668656 0.043 Uiso 1 1 calc R . . . . C3 C -0.2267(6) 0.4524(5) 0.5891(3) 0.0369(9) Uani 1 1 d . . . . . H3 H -0.372274 0.393514 0.581921 0.044 Uiso 1 1 calc R . . . . C4 C 0.2120(6) 0.6281(5) 0.6128(3) 0.0382(9) Uani 1 1 d . . . . . H4 H 0.358007 0.686888 0.621556 0.046 Uiso 1 1 calc R . . . . C5 C 0.2761(6) 1.1898(4) 0.7758(3) 0.0343(8) Uani 1 1 d . . . . . H5 H 0.133278 1.240988 0.768730 0.041 Uiso 1 1 calc R . . . . C6 C 0.2706(6) 1.1081(4) 0.5603(3) 0.0350(8) Uani 1 1 d . . . . . H6 H 0.124236 1.151637 0.533943 0.042 Uiso 1 1 calc R . . . . C7 C 0.3671(6) 1.1174(5) 0.6774(3) 0.0354(9) Uani 1 1 d . . . . . C8 C 0.6123(5) 0.9659(4) 0.5212(3) 0.0319(8) Uani 1 1 d . . . . . C9 C -0.1280(6) 0.5348(5) 0.6924(3) 0.0388(9) Uani 1 1 d . . . . . C10 C 0.1123(6) 0.5450(4) 0.5065(3) 0.0345(8) Uani 1 1 d . . . . . C11 C 0.5916(6) 1.0485(5) 0.7173(3) 0.0342(8) Uani 1 1 d . . . . . C12 C 0.0959(6) 0.6232(5) 0.7040(3) 0.0383(9) Uani 1 1 d . . . . . C13 C 0.4275(7) 1.1718(5) 0.8769(4) 0.0484(10) Uani 1 1 d . . . . . H13 H 0.397922 1.211061 0.948551 0.058 Uiso 1 1 calc R . . . . C14 C -0.0542(9) 0.6454(7) 0.8844(4) 0.0703(15) Uani 1 1 d . . . . . H14 H -0.073361 0.671913 0.960337 0.084 Uiso 0.768(2) 1 calc R . P A 1 H14A H -0.073361 0.671913 0.960337 0.084 Uiso 0.232(2) 1 calc R . P A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0448(7) 0.0541(7) 0.0455(7) 0.0031(5) 0.0045(4) 0.0047(5) C1A 0.0401(14) 0.0512(17) 0.0633(18) 0.0091(13) 0.0053(11) 0.0008(11) S2B 0.0453(8) 0.0522(9) 0.0561(9) -0.0065(6) 0.0021(6) 0.0013(6) S2A 0.0401(14) 0.0512(17) 0.0633(18) 0.0091(13) 0.0053(11) 0.0008(11) C1B 0.0453(8) 0.0522(9) 0.0561(9) -0.0065(6) 0.0021(6) 0.0013(6) C2 0.0269(18) 0.034(2) 0.045(2) 0.0076(16) 0.0039(14) 0.0038(15) C3 0.0271(18) 0.031(2) 0.051(2) 0.0032(17) 0.0043(15) -0.0004(15) C4 0.0276(18) 0.035(2) 0.050(2) 0.0029(17) 0.0017(15) 0.0030(15) C5 0.0287(18) 0.0274(19) 0.047(2) 0.0020(15) 0.0078(15) -0.0030(14) C6 0.0272(17) 0.0291(19) 0.048(2) 0.0046(16) 0.0048(15) 0.0036(14) C7 0.0274(18) 0.031(2) 0.049(2) 0.0049(16) 0.0096(15) 0.0011(15) C8 0.0230(18) 0.0261(18) 0.046(2) 0.0056(15) 0.0060(14) -0.0007(14) C9 0.0308(19) 0.036(2) 0.049(2) 0.0057(17) 0.0058(16) 0.0066(16) C10 0.0252(17) 0.0272(19) 0.049(2) 0.0032(15) 0.0027(14) 0.0019(14) C11 0.0293(18) 0.032(2) 0.041(2) 0.0071(15) 0.0043(14) 0.0021(15) C12 0.0296(19) 0.032(2) 0.051(2) 0.0031(17) 0.0006(15) 0.0016(15) C13 0.055(3) 0.044(2) 0.049(2) -0.0025(19) 0.0185(19) -0.006(2) C14 0.089(4) 0.079(4) 0.047(3) 0.004(2) 0.012(2) 0.038(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' S S 0.3331 0.5567 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 S1 C11 91.54(18) . . ? C9 C1A H1A 127.7 . . ? C14 C1A H1A 127.7 . . ? C14 C1A C9 104.7(3) . . ? C14 S2B C12 93.8(2) . . ? C14 S2A C9 104.7(3) . . ? C12 C1B H1B 133.1 . . ? C14 C1B H1B 133.1 . . ? C14 C1B C12 93.8(2) . . ? C8 C2 H2 120.1 . . ? C11 C2 H2 120.1 . . ? C11 C2 C8 119.9(3) . . ? C9 C3 H3 119.6 . . ? C9 C3 C10 120.9(3) . 2_566 ? C10 C3 H3 119.6 2_566 . ? C10 C4 H4 120.1 . . ? C12 C4 H4 120.1 . . ? C12 C4 C10 119.9(4) . . ? C7 C5 H5 124.9 . . ? C13 C5 H5 124.9 . . ? C13 C5 C7 110.3(3) . . ? C7 C6 H6 119.4 . . ? C7 C6 C8 121.2(3) . 2_676 ? C8 C6 H6 119.4 2_676 . ? C6 C7 C5 129.8(3) . . ? C6 C7 C11 119.0(3) . . ? C11 C7 C5 111.2(3) . . ? C2 C8 C6 121.5(3) . 2_676 ? C2 C8 C8 119.8(4) . 2_676 ? C6 C8 C8 118.6(4) 2_676 2_676 ? C3 C9 C1A 130.0(3) . . ? C3 C9 S2A 130.0(3) . . ? C3 C9 C12 119.6(4) . . ? C12 C9 C1A 110.4(3) . . ? C12 C9 S2A 110.4(3) . . ? C3 C10 C10 118.8(4) 2_566 2_566 ? C4 C10 C3 121.4(3) . 2_566 ? C4 C10 C10 119.8(4) . 2_566 ? C2 C11 S1 127.9(3) . . ? C2 C11 C7 121.4(3) . . ? C7 C11 S1 110.6(3) . . ? C4 C12 S2B 128.4(3) . . ? C4 C12 C1B 128.4(3) . . ? C4 C12 C9 121.0(4) . . ? C9 C12 S2B 110.5(3) . . ? C9 C12 C1B 110.5(3) . . ? S1 C13 H13 121.8 . . ? C5 C13 S1 116.3(3) . . ? C5 C13 H13 121.8 . . ? C1A C14 S2B 120.5(4) . . ? C1A C14 H14 119.7 . . ? S2B C14 H14 119.7 . . ? S2A C14 C1B 120.5(4) . . ? S2A C14 H14A 119.7 . . ? C1B C14 H14A 119.7 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C11 1.739(4) . ? S1 C13 1.713(4) . ? C1A H1A 0.9400 . ? C1A C9 1.602(5) . ? C1A C14 1.361(6) . ? S2B C12 1.720(4) . ? S2B C14 1.633(6) . ? S2A C9 1.602(5) . ? S2A C14 1.361(6) . ? C1B H1B 0.9400 . ? C1B C12 1.720(4) . ? C1B C14 1.633(6) . ? C2 H2 0.9400 . ? C2 C8 1.406(5) . ? C2 C11 1.372(5) . ? C3 H3 0.9400 . ? C3 C9 1.373(5) . ? C3 C10 1.413(5) 2_566 ? C4 H4 0.9400 . ? C4 C10 1.405(5) . ? C4 C12 1.374(5) . ? C5 H5 0.9400 . ? C5 C7 1.481(5) . ? C5 C13 1.349(5) . ? C6 H6 0.9400 . ? C6 C7 1.375(5) . ? C6 C8 1.417(5) 2_676 ? C7 C11 1.447(4) . ? C8 C8 1.450(6) 2_676 ? C9 C12 1.437(5) . ? C10 C10 1.445(7) 2_566 ? C13 H13 0.9400 . ? C14 H14 0.9400 . ? C14 H14A 0.9400 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A C9 C12 S2B 0.6(4) . . . . ? C1A C9 C12 C4 -179.5(3) . . . . ? S2A C9 C12 C1B 0.6(4) . . . . ? S2A C9 C12 C4 -179.5(3) . . . . ? C3 C9 C12 S2B -179.2(3) . . . . ? C3 C9 C12 C1B -179.2(3) . . . . ? C3 C9 C12 C4 0.7(5) . . . . ? C5 C7 C11 S1 0.4(4) . . . . ? C5 C7 C11 C2 -179.7(3) . . . . ? C6 C7 C11 S1 -179.6(3) . . . . ? C6 C7 C11 C2 0.4(5) . . . . ? C7 C5 C13 S1 -0.2(4) . . . . ? C8 C2 C11 S1 179.7(3) . . . . ? C8 C2 C11 C7 -0.2(6) . . . . ? C8 C6 C7 C5 179.5(3) 2_676 . . . ? C8 C6 C7 C11 -0.6(5) 2_676 . . . ? C9 C1A C14 S2B -0.3(4) . . . . ? C9 S2A C14 C1B -0.3(4) . . . . ? C10 C3 C9 C1A 179.5(3) 2_566 . . . ? C10 C3 C9 S2A 179.5(3) 2_566 . . . ? C10 C3 C9 C12 -0.7(5) 2_566 . . . ? C10 C4 C12 S2B 179.5(3) . . . . ? C10 C4 C12 C1B 179.5(3) . . . . ? C10 C4 C12 C9 -0.3(5) . . . . ? C11 S1 C13 C5 0.4(3) . . . . ? C11 C2 C8 C6 179.8(3) . . . 2_676 ? C11 C2 C8 C8 0.3(6) . . . 2_676 ? C12 S2B C14 C1A 0.6(4) . . . . ? C12 C1B C14 S2A 0.6(4) . . . . ? C12 C4 C10 C3 179.9(3) . . . 2_566 ? C12 C4 C10 C10 0.1(6) . . . 2_566 ? C13 S1 C11 C2 179.6(4) . . . . ? C13 S1 C11 C7 -0.4(3) . . . . ? C13 C5 C7 C6 179.8(4) . . . . ? C13 C5 C7 C11 -0.1(4) . . . . ? C14 C1A C9 C3 179.6(4) . . . . ? C14 C1A C9 C12 -0.2(4) . . . . ? C14 S2B C12 C4 179.5(4) . . . . ? C14 S2B C12 C9 -0.7(3) . . . . ? C14 S2A C9 C3 179.6(4) . . . . ? C14 S2A C9 C12 -0.2(4) . . . . ? C14 C1B C12 C4 179.5(4) . . . . ? C14 C1B C12 C9 -0.7(3) . . . . ?