# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Benzo[1,2-b:4,5-b']bis[b]benzothiophene as Solution Processible Organic Semiconductor for Field-Effect Transistors ; _publ_contact_author_address ; Max-Planck-Institut for Poymer Research Postfach 3148 D_55021 Mainz Germany ; _publ_contact_author_email MUELLEN@MPIP-MAINZ.MPG.DE _publ_contact_author_fax 'Int+6131 379100' _publ_contact_author_phone 'Int+6131 379133' _publ_contact_author_name 'Prof. K. Muellen' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; ; loop_ _publ_author_name K.Muellen D.Beckmann V.Enkelmann 'Xinliang Feng' 'Peng Gao' ; W.Pisula ; 'Hoi Nok Tsao' # Attachment 'Compound_1a.cif' data_gao3 _database_code_depnum_ccdc_archive 'CCDC 667690' _audit_creation_date 07-12-12 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'gao unsubst. 120K 10-07' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.4941(5) _cell_length_b 5.9036(4) _cell_length_c 11.5824(5) _cell_angle_alpha 90 _cell_angle_beta 102.9379(13) _cell_angle_gamma 90 _cell_volume 632.71(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C18 H10 S2 # Dc = 1.52 Fooo = 300.00 Mu = 4.04 M = 145.20 # Found Formula = C18 H10 S2 # Dc = 1.52 FOOO = 300.00 Mu = 4.04 M = 145.20 _chemical_formula_sum 'C18 H10 S2' _chemical_formula_moiety 'C18 H10 S2' _chemical_compound_source ? _chemical_formula_weight 290.41 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.19 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.48 _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.404 # Sheldrick geometric approximatio 0.88 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.93 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 8543 _reflns_number_total 1831 _diffrn_reflns_av_R_equivalents 0.035 # Number of reflections with Friedels Law is 1831 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1845 _diffrn_reflns_theta_min 4.095 _diffrn_reflns_theta_max 29.998 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.198 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.41 _refine_ls_number_reflns 1320 _refine_ls_number_restraints 0 _refine_ls_number_parameters 91 #_refine_ls_R_factor_ref 0.0307 _refine_ls_wR_factor_ref 0.0387 _refine_ls_goodness_of_fit_ref 1.0892 #_reflns_number_all 1831 _refine_ls_R_factor_all 0.0486 _refine_ls_wR_factor_all 0.0390 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1320 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_gt 0.0387 _refine_ls_shift/su_max 0.000714 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 26.0 -16.9 22.5 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.74849(3) 0.16147(5) 0.50447(3) 0.0157 1.0000 Uani . . . . . . C1 C 1.03768(13) 0.2994(2) 0.56927(11) 0.0135 1.0000 Uani . . . . . . C2 C 0.89643(13) 0.3411(2) 0.50862(10) 0.0126 1.0000 Uani . . . . . . C3 C 0.85710(13) 0.5397(2) 0.43954(10) 0.0121 1.0000 Uani . . . . . . C4 C 0.70376(13) 0.5426(2) 0.38399(10) 0.0130 1.0000 Uani . . . . . . C5 C 0.63187(13) 0.3482(2) 0.41230(10) 0.0139 1.0000 Uani . . . . . . C6 C 0.48278(14) 0.3194(2) 0.37036(12) 0.0177 1.0000 Uani . . . . . . C7 C 0.40657(14) 0.4858(2) 0.29751(11) 0.0184 1.0000 Uani . . . . . . C8 C 0.47680(14) 0.6774(2) 0.26579(11) 0.0179 1.0000 Uani . . . . . . C9 C 0.62499(14) 0.7068(2) 0.30894(11) 0.0157 1.0000 Uani . . . . . . H11 H 1.0603 0.1641 0.6157 0.0500 1.0000 Uiso R . . . . . H61 H 0.4370 0.1865 0.3927 0.0500 1.0000 Uiso R . . . . . H71 H 0.3040 0.4709 0.2686 0.0500 1.0000 Uiso R . . . . . H81 H 0.4227 0.7886 0.2136 0.0500 1.0000 Uiso R . . . . . H91 H 0.6723 0.8393 0.2881 0.0500 1.0000 Uiso R . . . . . 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 0.01382(16) 0.01401(16) 0.01906(16) 0.00220(11) 0.00297(10) -0.00288(11) C1 0.0144(5) 0.0126(5) 0.0137(5) 0.0020(4) 0.0035(4) 0.0000(4) C2 0.0128(5) 0.0130(5) 0.0125(5) -0.0006(4) 0.0037(4) -0.0025(4) C3 0.0132(5) 0.0121(5) 0.0110(5) -0.0010(4) 0.0024(4) -0.0001(4) C4 0.0128(5) 0.0145(5) 0.0116(5) -0.0017(4) 0.0028(4) -0.0004(4) C5 0.0133(5) 0.0159(6) 0.0126(5) -0.0011(4) 0.0031(4) -0.0002(5) C6 0.0143(6) 0.0220(6) 0.0171(5) -0.0032(5) 0.0040(4) -0.0041(5) C7 0.0117(5) 0.0262(7) 0.0164(5) -0.0034(5) 0.0015(4) -0.0002(5) C8 0.0157(6) 0.0211(6) 0.0161(5) 0.0004(5) 0.0018(4) 0.0036(5) C9 0.0156(6) 0.0175(6) 0.0139(5) -0.0004(4) 0.0027(4) 0.0004(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.95(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . C2 . 1.7520(12) yes S1 . C5 . 1.7469(13) yes C1 . C3 2_766 1.3987(17) yes C1 . C2 . 1.3894(17) yes C1 . H11 . 0.960 no C2 . C3 . 1.4213(17) yes C3 . C4 . 1.4540(17) yes C4 . C5 . 1.4110(17) yes C4 . C9 . 1.4010(17) yes C5 . C6 . 1.4002(17) yes C6 . C7 . 1.3882(19) yes C6 . H61 . 0.960 no C7 . C8 . 1.403(2) yes C7 . H71 . 0.960 no C8 . C9 . 1.3944(18) yes C8 . H81 . 0.960 no C9 . H91 . 0.960 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . S1 . C5 . 91.68(6) yes C3 2_766 C1 . C2 . 117.84(11) yes C3 2_766 C1 . H11 . 122.159 no C2 . C1 . H11 . 120.001 no S1 . C2 . C1 . 125.71(10) yes S1 . C2 . C3 . 112.07(9) yes C1 . C2 . C3 . 122.20(11) yes C2 . C3 . C1 2_766 119.96(11) yes C2 . C3 . C4 . 111.71(11) yes C1 2_766 C3 . C4 . 128.33(11) yes C3 . C4 . C5 . 112.08(11) yes C3 . C4 . C9 . 128.71(12) yes C5 . C4 . C9 . 119.21(11) yes C4 . C5 . S1 . 112.46(9) yes C4 . C5 . C6 . 121.48(12) yes S1 . C5 . C6 . 126.06(11) yes C5 . C6 . C7 . 118.28(13) yes C5 . C6 . H61 . 119.292 no C7 . C6 . H61 . 122.425 no C6 . C7 . C8 . 121.07(12) yes C6 . C7 . H71 . 119.797 no C8 . C7 . H71 . 119.134 no C7 . C8 . C9 . 120.45(12) yes C7 . C8 . H81 . 119.849 no C9 . C8 . H81 . 119.703 no C4 . C9 . C8 . 119.48(12) yes C4 . C9 . H91 . 120.335 no C8 . C9 . H91 . 120.181 no # Attachment 'Compound_1b.cif' data_gao2 _database_code_depnum_ccdc_archive 'CCDC 667691' _audit_creation_date 07-12-12 _audit_creation_method CRYSTALS_ver_12.39 _oxford_structure_analysis_title 'gaoC4 120K 10-07' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 4.5840(4) _cell_length_b 9.2230(5) _cell_length_c 12.4880(5) _cell_angle_alpha 89.8540(12) _cell_angle_beta 79.5940(13) _cell_angle_gamma 79.1590(13) _cell_volume 509.75(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C26 H26 S2 # Dc = 1.31 Fooo = 214.00 Mu = 2.71 M = 201.31 # Found Formula = C26 H26 S2 # Dc = 1.31 FOOO = 214.00 Mu = 2.71 M = 201.31 _chemical_formula_sum 'C26 H26 S2' _chemical_formula_moiety 'C26 H26 S2' _chemical_compound_source ? _chemical_formula_weight 402.62 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.39 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 214 _exptl_absorpt_coefficient_mu 0.271 # Sheldrick geometric approximatio 0.93 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 10704 _reflns_number_total 2584 _diffrn_reflns_av_R_equivalents 0.084 # Number of reflections with Friedels Law is 2584 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2635 _diffrn_reflns_theta_min 4.502 _diffrn_reflns_theta_max 28.701 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 25.257 _diffrn_measured_fraction_theta_full 0.923 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.76 _refine_diff_density_max 1.08 _refine_ls_number_reflns 2103 _refine_ls_number_restraints 0 _refine_ls_number_parameters 127 #_refine_ls_R_factor_ref 0.0701 _refine_ls_wR_factor_ref 0.0565 _refine_ls_goodness_of_fit_ref 0.9129 #_reflns_number_all 2365 _refine_ls_R_factor_all 0.0702 _refine_ls_wR_factor_all 0.0565 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2103 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_gt 0.0565 _refine_ls_shift/su_max 0.000257 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 3.16 0.205 1.19 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Blessing, SORTAV ( ) Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.54339(12) 0.79951(6) 0.54116(4) 0.0191 1.0000 Uani . . . . . . C2 C 0.8054(4) 0.6322(2) 0.52620(18) 0.0166 1.0000 Uani . . . . . . C3 C 0.8139(4) 0.5577(2) 0.42632(17) 0.0168 1.0000 Uani . . . . . . C4 C 0.6048(5) 0.6379(2) 0.36286(16) 0.0170 1.0000 Uani . . . . . . C5 C 0.4427(5) 0.7712(2) 0.41492(17) 0.0179 1.0000 Uani . . . . . . C6 C 0.1793(5) 0.8300(2) 0.26602(17) 0.0172 1.0000 Uani . . . . . . C7 C 0.2310(5) 0.8661(2) 0.36853(18) 0.0187 1.0000 Uani . . . . . . C8 C 0.3407(5) 0.6965(2) 0.21357(17) 0.0192 1.0000 Uani . . . . . . C9 C 0.5494(5) 0.6013(2) 0.26060(18) 0.0208 1.0000 Uani . . . . . . C10 C 0.9865(5) 0.5779(2) 0.59969(18) 0.0197 1.0000 Uani . . . . . . C11 C -0.0305(5) 0.9382(2) 0.21188(18) 0.0207 1.0000 Uani . . . . . . C12 C 0.1201(5) 1.0626(2) 0.1610(2) 0.0230 1.0000 Uani . . . . . . C13 C -0.0911(5) 1.1816(3) 0.1124(2) 0.0258 1.0000 Uani . . . . . . C14 C 0.0628(7) 1.3025(3) 0.0607(2) 0.0335 1.0000 Uani . . . . . . H71 H 0.1218 0.9548 0.4061 0.0275 1.0000 Uiso R . . . . . H81 H 0.3081 0.6714 0.1435 0.0237 1.0000 Uiso R . . . . . H91 H 0.6579 0.5121 0.2236 0.0294 1.0000 Uiso R . . . . . H101 H 0.9782 0.6317 0.6653 0.0276 1.0000 Uiso R . . . . . H111 H -0.1978 0.9810 0.2661 0.0294 1.0000 Uiso R . . . . . H112 H -0.0996 0.8892 0.1573 0.0294 1.0000 Uiso R . . . . . H121 H 0.1982 1.1077 0.2151 0.0334 1.0000 Uiso R . . . . . H122 H 0.2815 1.0196 0.1046 0.0334 1.0000 Uiso R . . . . . H131 H -0.2534 1.2243 0.1686 0.0357 1.0000 Uiso R . . . . . H132 H -0.1681 1.1369 0.0578 0.0357 1.0000 Uiso R . . . . . H141 H -0.0774 1.3739 0.0315 0.0485 1.0000 Uiso R . . . . . H142 H 0.1395 1.3485 0.1148 0.0485 1.0000 Uiso R . . . . . H143 H 0.2247 1.2610 0.0040 0.0485 1.0000 Uiso R . . . . . 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 0.0175(2) 0.0207(3) 0.0186(3) 0.00017(18) -0.00274(18) -0.00277(18) C2 0.0120(8) 0.0151(8) 0.0223(10) 0.0007(7) 0.0005(7) -0.0053(7) C3 0.0149(9) 0.0163(9) 0.0203(10) 0.0036(7) -0.0025(7) -0.0069(7) C4 0.0175(9) 0.0189(9) 0.0161(9) 0.0012(7) -0.0033(7) -0.0069(7) C5 0.0159(9) 0.0195(9) 0.0202(10) 0.0034(8) -0.0026(7) -0.0084(7) C6 0.0170(9) 0.0153(9) 0.0206(10) 0.0048(7) -0.0032(7) -0.0066(7) C7 0.0144(9) 0.0199(9) 0.0212(10) 0.0017(8) -0.0001(7) -0.0052(7) C8 0.0218(10) 0.0233(10) 0.0145(9) 0.0022(8) -0.0049(7) -0.0075(8) C9 0.0212(10) 0.0200(9) 0.0204(10) 0.0008(8) 0.0002(8) -0.0060(8) C10 0.0188(9) 0.0174(9) 0.0225(10) 0.0035(8) -0.0004(8) -0.0059(8) C11 0.0209(10) 0.0206(10) 0.0217(10) 0.0026(8) -0.0059(8) -0.0048(8) C12 0.0220(10) 0.0210(10) 0.0253(10) 0.0043(8) -0.0028(8) -0.0043(8) C13 0.0255(11) 0.0263(11) 0.0276(12) 0.0054(9) -0.0101(9) -0.0055(9) C14 0.0408(14) 0.0276(12) 0.0343(14) 0.0116(10) -0.0099(11) -0.0095(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.628(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . C2 . 1.756(2) yes S1 . C5 . 1.754(2) yes C2 . C3 . 1.416(3) yes C2 . C10 . 1.378(3) yes C3 . C10 2_766 1.404(3) yes C3 . C4 . 1.449(3) yes C4 . C5 . 1.404(3) yes C4 . C9 . 1.400(3) yes C5 . C7 . 1.387(3) yes C6 . C7 . 1.395(3) yes C6 . C8 . 1.407(3) yes C6 . C11 . 1.499(3) yes C7 . H71 . 0.950 no C8 . C9 . 1.384(3) yes C8 . H81 . 0.950 no C9 . H91 . 0.950 no C10 . H101 . 0.950 no C11 . C12 . 1.527(3) yes C11 . H111 . 0.950 no C11 . H112 . 0.950 no C12 . C13 . 1.522(3) yes C12 . H121 . 0.950 no C12 . H122 . 0.950 no C13 . C14 . 1.512(3) yes C13 . H131 . 0.950 no C13 . H132 . 0.950 no C14 . H141 . 0.950 no C14 . H142 . 0.950 no C14 . H143 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . S1 . C5 . 91.89(10) yes S1 . C2 . C3 . 111.38(16) yes S1 . C2 . C10 . 125.71(17) yes C3 . C2 . C10 . 122.90(19) yes C2 . C3 . C10 2_766 119.15(19) yes C2 . C3 . C4 . 112.40(18) yes C10 2_766 C3 . C4 . 128.46(19) yes C3 . C4 . C5 . 112.36(18) yes C3 . C4 . C9 . 129.36(19) yes C5 . C4 . C9 . 118.28(19) yes S1 . C5 . C4 . 111.97(15) yes S1 . C5 . C7 . 125.86(17) yes C4 . C5 . C7 . 122.2(2) yes C7 . C6 . C8 . 118.70(19) yes C7 . C6 . C11 . 119.37(19) yes C8 . C6 . C11 . 121.82(19) yes C6 . C7 . C5 . 119.4(2) yes C6 . C7 . H71 . 120.170 no C5 . C7 . H71 . 120.470 no C6 . C8 . C9 . 121.8(2) yes C6 . C8 . H81 . 119.261 no C9 . C8 . H81 . 118.946 no C4 . C9 . C8 . 119.7(2) yes C4 . C9 . H91 . 119.665 no C8 . C9 . H91 . 120.626 no C3 2_766 C10 . C2 . 118.0(2) yes C3 2_766 C10 . H101 . 121.285 no C2 . C10 . H101 . 120.756 no C6 . C11 . C12 . 111.95(18) yes C6 . C11 . H111 . 107.789 no C12 . C11 . H111 . 107.974 no C6 . C11 . H112 . 110.204 no C12 . C11 . H112 . 109.393 no H111 . C11 . H112 . 109.467 no C11 . C12 . C13 . 113.90(19) yes C11 . C12 . H121 . 108.879 no C13 . C12 . H121 . 108.467 no C11 . C12 . H122 . 107.537 no C13 . C12 . H122 . 108.533 no H121 . C12 . H122 . 109.467 no C12 . C13 . C14 . 113.2(2) yes C12 . C13 . H131 . 108.656 no C14 . C13 . H131 . 108.879 no C12 . C13 . H132 . 108.594 no C14 . C13 . H132 . 107.990 no H131 . C13 . H132 . 109.467 no C13 . C14 . H141 . 110.152 no C13 . C14 . H142 . 108.676 no H141 . C14 . H142 . 109.476 no C13 . C14 . H143 . 109.568 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no