# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 data_General _audit_creation_date 2013-07-12 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Ken-ichi Sakai' _publ_contact_author_email k-sakai@photon.chitose.ac.jp _publ_contact_author_fax +81-123-27-6054 _publ_contact_author_phone +81-123-27-6054 _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal CrystEngComm _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name 'Ken-ichi Sakai' 'Hiroshi Kawamura' 'Takaaki Ishikawa' 'Noriyuki Kobayashi' 'Chiori Ikeda' 'Takemitsu Kikuchi' 'Tomoyuki Akutagawa' #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. SHELX97 Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_2,6-bis(benzothiazol-2-yl)-4-methoxyphenol #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C21 H14 N2 O2 S2' _chemical_formula_moiety 'C21 H14 N2 O2 S2' _chemical_formula_weight 390.47 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 37.1672(11) _cell_length_b 3.83724(10) _cell_length_c 30.9227(8) _cell_angle_alpha 90.0000 _cell_angle_beta 130.2768(13) _cell_angle_gamma 90.0000 _cell_volume 3364.66(17) _cell_formula_units_Z 8 _cell_measurement_reflns_used 6314 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 68.21 _cell_measurement_temperature 100 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616.00 _exptl_absorpt_coefficient_mu 3.041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.377 _exptl_absorpt_correction_T_max 0.859 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 16643 _diffrn_reflns_av_R_equivalents 0.1861 _diffrn_reflns_theta_max 68.25 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3068 _reflns_number_gt 1929 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.2371 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3068 _refine_ls_number_parameters 248 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.670 _refine_diff_density_min -0.490 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.3331 0.5567 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.20240(5) 1.0137(4) -0.01628(6) 0.0402(5) Uani 1.0 8 d . . . S2 S 0.05635(5) 0.6868(4) 0.05621(5) 0.0359(5) Uani 1.0 8 d . . . O1 O 0.09339(13) 0.8774(11) 0.00784(16) 0.0391(10) Uani 1.0 8 d . . . O2 O 0.27708(12) 0.4418(11) 0.17580(15) 0.0405(11) Uani 1.0 8 d . . . N1 N 0.11660(16) 1.0257(12) -0.05346(19) 0.0372(12) Uani 1.0 8 d . . . N2 N 0.12815(15) 0.4151(12) 0.15208(18) 0.0342(11) Uani 1.0 8 d . . . C1 C 0.15996(19) 0.9462(15) -0.0092(3) 0.0359(14) Uani 1.0 8 d . . . C2 C 0.1145(2) 1.1425(15) -0.0980(3) 0.0381(14) Uani 1.0 8 d . . . C3 C 0.0738(2) 1.2381(16) -0.1516(3) 0.0400(15) Uani 1.0 8 d . . . C4 C 0.0773(3) 1.3449(16) -0.1913(3) 0.0455(16) Uani 1.0 8 d . . . C5 C 0.1208(3) 1.3575(16) -0.1782(3) 0.0476(16) Uani 1.0 8 d . . . C6 C 0.1618(2) 1.2621(16) -0.1255(3) 0.0407(15) Uani 1.0 8 d . . . C7 C 0.1583(2) 1.1536(16) -0.0857(3) 0.0410(15) Uani 1.0 8 d . . . C8 C 0.17299(19) 0.8050(15) 0.0434(3) 0.0351(14) Uani 1.0 8 d . . . C9 C 0.21894(19) 0.6898(15) 0.0872(3) 0.0369(14) Uani 1.0 8 d . . . C10 C 0.2308(2) 0.5455(16) 0.1360(3) 0.0362(14) Uani 1.0 8 d . . . C11 C 0.19694(19) 0.5139(15) 0.1412(3) 0.0359(14) Uani 1.0 8 d . . . C12 C 0.15049(18) 0.6201(15) 0.0981(3) 0.0343(13) Uani 1.0 8 d . . . C13 C 0.13839(19) 0.7687(16) 0.0490(3) 0.0360(14) Uani 1.0 8 d . . . C14 C 0.11612(18) 0.5647(15) 0.1065(3) 0.0345(14) Uani 1.0 8 d . . . C15 C 0.08973(18) 0.3827(15) 0.1497(3) 0.0338(13) Uani 1.0 8 d . . . C16 C 0.0902(2) 0.2301(16) 0.1909(3) 0.0371(14) Uani 1.0 8 d . . . C17 C 0.0489(2) 0.2102(15) 0.1818(3) 0.0390(14) Uani 1.0 8 d . . . C18 C 0.0068(2) 0.3410(16) 0.1323(3) 0.0393(15) Uani 1.0 8 d . . . C19 C 0.0049(2) 0.4977(16) 0.0907(3) 0.0394(15) Uani 1.0 8 d . . . C20 C 0.0473(2) 0.5171(15) 0.1003(3) 0.0344(13) Uani 1.0 8 d . . . C21 C 0.29047(19) 0.2774(17) 0.2261(3) 0.0423(15) Uani 1.0 8 d . . . H1 H 0.091(3) 0.925(19) -0.022(3) 0.08(3) Uiso 1.0 8 d . . . H3 H 0.0440 1.2300 -0.1607 0.0480 Uiso 1.0 8 calc R . . H4 H 0.0497 1.4110 -0.2280 0.0546 Uiso 1.0 8 calc R . . H5 H 0.1223 1.4335 -0.2063 0.0571 Uiso 1.0 8 calc R . . H6 H 0.1914 1.2705 -0.1168 0.0489 Uiso 1.0 8 calc R . . H9 H 0.2423 0.7110 0.0835 0.0443 Uiso 1.0 8 calc R . . H11 H 0.2053 0.4174 0.1750 0.0430 Uiso 1.0 8 calc R . . H16 H 0.1187 0.1411 0.2248 0.0445 Uiso 1.0 8 calc R . . H17 H 0.0490 0.1058 0.2098 0.0468 Uiso 1.0 8 calc R . . H18 H -0.0213 0.3213 0.1270 0.0471 Uiso 1.0 8 calc R . . H19 H -0.0238 0.5884 0.0572 0.0473 Uiso 1.0 8 calc R . . H21A H 0.2893 0.4486 0.2487 0.0508 Uiso 1.0 8 calc R . . H21B H 0.3226 0.1852 0.2484 0.0508 Uiso 1.0 8 calc R . . H21C H 0.2686 0.0862 0.2154 0.0508 Uiso 1.0 8 calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0433(9) 0.0396(10) 0.0388(9) 0.0002(7) 0.0270(8) 0.0041(7) S2 0.0392(8) 0.0339(10) 0.0327(8) -0.0013(6) 0.0224(7) -0.0008(6) O1 0.038(3) 0.043(3) 0.032(3) 0.0017(18) 0.0205(19) 0.0069(19) O2 0.038(3) 0.040(3) 0.035(3) 0.0043(18) 0.0203(19) 0.0065(18) N1 0.043(3) 0.031(3) 0.033(3) 0.000(3) 0.022(3) 0.001(2) N2 0.038(3) 0.029(3) 0.032(3) -0.004(2) 0.021(3) -0.002(2) C1 0.039(4) 0.029(4) 0.037(4) 0.002(3) 0.023(3) -0.004(3) C2 0.052(4) 0.030(4) 0.034(3) 0.001(3) 0.029(3) -0.003(3) C3 0.046(4) 0.035(4) 0.035(3) 0.008(3) 0.024(3) 0.003(3) C4 0.060(4) 0.034(4) 0.034(4) 0.001(3) 0.026(3) 0.003(3) C5 0.066(5) 0.037(4) 0.044(4) 0.000(4) 0.038(4) 0.003(3) C6 0.051(4) 0.033(4) 0.043(4) 0.003(3) 0.032(3) 0.005(3) C7 0.053(4) 0.028(4) 0.043(4) -0.007(3) 0.031(3) -0.006(3) C8 0.040(4) 0.029(4) 0.032(3) 0.001(3) 0.022(3) 0.004(3) C9 0.041(4) 0.034(4) 0.035(3) -0.002(3) 0.025(3) -0.000(3) C10 0.038(4) 0.033(4) 0.033(3) 0.002(3) 0.021(3) -0.003(3) C11 0.042(4) 0.031(4) 0.032(3) -0.001(3) 0.023(3) 0.002(3) C12 0.031(3) 0.034(4) 0.033(3) -0.002(3) 0.019(3) -0.004(3) C13 0.035(3) 0.031(4) 0.033(3) 0.002(3) 0.018(3) -0.006(3) C14 0.037(4) 0.032(4) 0.029(3) 0.000(3) 0.018(3) -0.006(3) C15 0.036(3) 0.032(4) 0.029(3) -0.004(3) 0.019(3) -0.008(3) C16 0.047(4) 0.029(4) 0.034(3) -0.001(3) 0.026(3) -0.003(3) C17 0.053(4) 0.030(4) 0.033(3) -0.004(3) 0.027(3) -0.003(3) C18 0.045(4) 0.038(4) 0.039(4) -0.009(3) 0.029(3) -0.007(3) C19 0.042(4) 0.039(4) 0.030(3) -0.003(3) 0.020(3) -0.007(3) C20 0.046(4) 0.024(4) 0.028(3) -0.007(3) 0.021(3) -0.004(3) C21 0.038(4) 0.045(5) 0.033(3) -0.001(3) 0.019(3) 0.003(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C1 1.746(9) yes . . S1 C7 1.742(6) yes . . S2 C14 1.762(5) yes . . S2 C20 1.730(9) yes . . O1 C13 1.356(6) yes . . O2 C10 1.376(7) yes . . O2 C21 1.435(9) yes . . N1 C1 1.308(6) yes . . N1 C2 1.402(11) yes . . N2 C14 1.303(9) yes . . N2 C15 1.386(11) yes . . C1 C8 1.468(10) yes . . C2 C3 1.387(7) yes . . C2 C7 1.412(12) yes . . C3 C4 1.378(13) yes . . C4 C5 1.392(13) yes . . C5 C6 1.379(7) yes . . C6 C7 1.385(13) yes . . C8 C9 1.399(7) yes . . C8 C13 1.411(13) yes . . C9 C10 1.384(10) yes . . C10 C11 1.374(13) yes . . C11 C12 1.396(7) yes . . C12 C13 1.397(10) yes . . C12 C14 1.476(12) yes . . C15 C16 1.392(12) yes . . C15 C20 1.404(7) yes . . C16 C17 1.374(12) yes . . C17 C18 1.396(7) yes . . C18 C19 1.377(12) yes . . C19 C20 1.404(12) yes . . O1 H1 0.91(11) no . . C3 H3 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C9 H9 0.950 no . . C11 H11 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C21 H21A 0.980 no . . C21 H21B 0.980 no . . C21 H21C 0.980 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 S1 C7 89.5(4) yes . . . C14 S2 C20 88.9(4) yes . . . C10 O2 C21 117.0(6) yes . . . C1 N1 C2 110.6(7) yes . . . C14 N2 C15 111.1(5) yes . . . S1 C1 N1 115.9(6) yes . . . S1 C1 C8 121.0(4) yes . . . N1 C1 C8 123.1(8) yes . . . N1 C2 C3 125.7(8) yes . . . N1 C2 C7 114.9(5) yes . . . C3 C2 C7 119.4(8) yes . . . C2 C3 C4 119.0(8) yes . . . C3 C4 C5 120.9(5) yes . . . C4 C5 C6 121.5(9) yes . . . C5 C6 C7 117.6(8) yes . . . S1 C7 C2 109.1(6) yes . . . S1 C7 C6 129.3(6) yes . . . C2 C7 C6 121.6(5) yes . . . C1 C8 C9 120.9(8) yes . . . C1 C8 C13 119.9(5) yes . . . C9 C8 C13 119.2(7) yes . . . C8 C9 C10 120.9(8) yes . . . O2 C10 C9 115.1(8) yes . . . O2 C10 C11 125.4(7) yes . . . C9 C10 C11 119.5(5) yes . . . C10 C11 C12 121.5(7) yes . . . C11 C12 C13 119.2(8) yes . . . C11 C12 C14 117.8(7) yes . . . C13 C12 C14 123.0(5) yes . . . O1 C13 C8 121.6(7) yes . . . O1 C13 C12 118.7(8) yes . . . C8 C13 C12 119.7(5) yes . . . S2 C14 N2 115.3(6) yes . . . S2 C14 C12 123.1(5) yes . . . N2 C14 C12 121.6(5) yes . . . N2 C15 C16 125.8(5) yes . . . N2 C15 C20 114.9(7) yes . . . C16 C15 C20 119.4(7) yes . . . C15 C16 C17 119.1(5) yes . . . C16 C17 C18 121.0(8) yes . . . C17 C18 C19 121.8(8) yes . . . C18 C19 C20 116.9(5) yes . . . S2 C20 C15 109.9(6) yes . . . S2 C20 C19 128.2(4) yes . . . C15 C20 C19 121.9(7) yes . . . C13 O1 H1 105(5) no . . . C2 C3 H3 120.513 no . . . C4 C3 H3 120.526 no . . . C3 C4 H4 119.533 no . . . C5 C4 H4 119.541 no . . . C4 C5 H5 119.284 no . . . C6 C5 H5 119.256 no . . . C5 C6 H6 121.206 no . . . C7 C6 H6 121.183 no . . . C8 C9 H9 119.575 no . . . C10 C9 H9 119.569 no . . . C10 C11 H11 119.213 no . . . C12 C11 H11 119.243 no . . . C15 C16 H16 120.504 no . . . C17 C16 H16 120.443 no . . . C16 C17 H17 119.494 no . . . C18 C17 H17 119.478 no . . . C17 C18 H18 119.116 no . . . C19 C18 H18 119.124 no . . . C18 C19 H19 121.568 no . . . C20 C19 H19 121.559 no . . . O2 C21 H21A 109.475 no . . . O2 C21 H21B 109.487 no . . . O2 C21 H21C 109.479 no . . . H21A C21 H21B 109.475 no . . . H21A C21 H21C 109.434 no . . . H21B C21 H21C 109.477 no . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 S1 C7 C2 0.7(4) no . . . . C1 S1 C7 C6 -179.1(6) no . . . . C7 S1 C1 N1 -1.3(5) no . . . . C7 S1 C1 C8 178.0(5) no . . . . C14 S2 C20 C15 0.3(4) no . . . . C14 S2 C20 C19 -178.1(5) no . . . . C20 S2 C14 N2 -0.6(5) no . . . . C20 S2 C14 C12 178.3(5) no . . . . C21 O2 C10 C9 -177.5(5) no . . . . C21 O2 C10 C11 2.0(8) no . . . . C1 N1 C2 C3 178.0(5) no . . . . C1 N1 C2 C7 -0.9(7) no . . . . C2 N1 C1 S1 1.5(7) no . . . . C2 N1 C1 C8 -177.9(5) no . . . . C14 N2 C15 C16 179.0(5) no . . . . C14 N2 C15 C20 -0.6(7) no . . . . C15 N2 C14 S2 0.8(7) no . . . . C15 N2 C14 C12 -178.2(5) no . . . . S1 C1 C8 C9 -6.1(8) no . . . . S1 C1 C8 C13 176.9(4) no . . . . N1 C1 C8 C9 173.2(5) no . . . . N1 C1 C8 C13 -3.8(9) no . . . . N1 C2 C3 C4 -179.4(5) no . . . . N1 C2 C7 S1 -0.1(7) no . . . . N1 C2 C7 C6 179.8(5) no . . . . C3 C2 C7 S1 -179.0(5) no . . . . C3 C2 C7 C6 0.8(9) no . . . . C7 C2 C3 C4 -0.6(9) no . . . . C2 C3 C4 C5 0.0(9) no . . . . C3 C4 C5 C6 0.4(10) no . . . . C4 C5 C6 C7 -0.2(9) no . . . . C5 C6 C7 S1 179.4(5) no . . . . C5 C6 C7 C2 -0.4(9) no . . . . C1 C8 C9 C10 -177.8(5) no . . . . C1 C8 C13 O1 -3.3(9) no . . . . C1 C8 C13 C12 177.2(5) no . . . . C9 C8 C13 O1 179.7(5) no . . . . C9 C8 C13 C12 0.2(8) no . . . . C13 C8 C9 C10 -0.8(9) no . . . . C8 C9 C10 O2 179.8(5) no . . . . C8 C9 C10 C11 0.3(9) no . . . . O2 C10 C11 C12 -178.7(5) no . . . . C9 C10 C11 C12 0.8(9) no . . . . C10 C11 C12 C13 -1.3(9) no . . . . C10 C11 C12 C14 177.9(5) no . . . . C11 C12 C13 O1 -178.7(5) no . . . . C11 C12 C13 C8 0.8(9) no . . . . C11 C12 C14 S2 179.7(5) no . . . . C11 C12 C14 N2 -1.4(8) no . . . . C13 C12 C14 S2 -1.2(9) no . . . . C13 C12 C14 N2 177.7(5) no . . . . C14 C12 C13 O1 2.2(9) no . . . . C14 C12 C13 C8 -178.3(5) no . . . . N2 C15 C16 C17 -178.5(5) no . . . . N2 C15 C20 S2 0.1(7) no . . . . N2 C15 C20 C19 178.6(5) no . . . . C16 C15 C20 S2 -179.5(5) no . . . . C16 C15 C20 C19 -1.0(9) no . . . . C20 C15 C16 C17 1.0(9) no . . . . C15 C16 C17 C18 -0.2(9) no . . . . C16 C17 C18 C19 -0.6(9) no . . . . C17 C18 C19 C20 0.6(9) no . . . . C18 C19 C20 S2 178.4(5) no . . . . C18 C19 C20 C15 0.2(9) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 C9 3.102(8) no . . S2 O1 2.707(7) no . . S2 C13 3.214(9) no . . O1 N1 2.603(10) no . . O1 C1 2.856(11) no . . O1 C14 2.852(9) no . . N1 C13 2.888(10) no . . N2 C11 2.811(11) no . . C1 C3 3.558(7) no . . C2 C5 2.765(13) no . . C3 C6 2.819(12) no . . C4 C7 2.747(7) no . . C8 C11 2.778(10) no . . C9 C12 2.786(12) no . . C10 C13 2.797(7) no . . C11 C21 2.828(7) no . . C14 C16 3.553(12) no . . C15 C18 2.769(12) no . . C16 C19 2.829(7) no . . C17 C20 2.747(12) no . . S1 S1 3.495(3) no . 7_575 S2 S2 3.5857(18) no . 3_565 S2 C15 3.519(7) no . 1_565 S2 C19 3.600(7) no . 3_565 S2 C20 3.566(7) no . 1_565 O1 C12 3.571(7) no . 1_565 O1 C18 3.533(6) no . 3_565 O1 C19 3.211(6) no . 3_565 O2 C6 3.572(12) no . 7_565 O2 C9 3.584(7) no . 1_545 O2 C21 3.456(8) no . 1_565 N2 C14 3.467(8) no . 1_545 N2 C21 3.247(7) no . 6_555 C1 C8 3.566(9) no . 1_565 C6 O2 3.572(12) no . 7_565 C8 C1 3.566(9) no . 1_545 C8 C10 3.598(8) no . 1_565 C9 O2 3.584(7) no . 1_565 C9 C10 3.520(9) no . 1_565 C10 C8 3.598(8) no . 1_545 C10 C9 3.520(9) no . 1_545 C10 C21 3.546(8) no . 1_565 C12 O1 3.571(7) no . 1_545 C12 C13 3.507(9) no . 1_545 C13 C12 3.507(9) no . 1_565 C14 N2 3.467(8) no . 1_565 C15 S2 3.519(7) no . 1_545 C15 C16 3.489(9) no . 1_565 C15 C20 3.569(8) no . 1_545 C16 C15 3.489(9) no . 1_545 C16 C20 3.478(8) no . 1_545 C17 C18 3.581(8) no . 1_545 C17 C19 3.483(9) no . 1_545 C18 O1 3.533(6) no . 3_565 C18 C17 3.581(8) no . 1_565 C18 C19 3.465(9) no . 1_545 C19 S2 3.600(7) no . 3_565 C19 O1 3.211(6) no . 3_565 C19 C17 3.483(9) no . 1_565 C19 C18 3.465(9) no . 1_565 C20 S2 3.566(7) no . 1_545 C20 C15 3.569(8) no . 1_565 C20 C16 3.478(8) no . 1_565 C21 O2 3.456(8) no . 1_545 C21 N2 3.247(7) no . 6_545 C21 C10 3.546(8) no . 1_545 S1 H6 3.0269 no . . S1 H9 2.6746 no . . S2 H1 3.54(12) no . . S2 H19 3.0208 no . . O2 H9 2.4725 no . . O2 H11 2.6517 no . . N1 H1 1.76(12) no . . N1 H3 2.7066 no . . N2 H11 2.4709 no . . N2 H16 2.7025 no . . C1 H1 2.31(11) no . . C1 H9 2.6563 no . . C2 H1 3.08(12) no . . C2 H4 3.2404 no . . C2 H6 3.3028 no . . C3 H5 3.2587 no . . C4 H6 3.2776 no . . C5 H3 3.2685 no . . C6 H4 3.2655 no . . C7 H3 3.2805 no . . C7 H5 3.2252 no . . C8 H1 2.36(7) no . . C9 H11 3.2377 no . . C10 H21A 2.6849 no . . C10 H21B 3.2081 no . . C10 H21C 2.5785 no . . C11 H9 3.2386 no . . C11 H21A 2.8537 no . . C11 H21C 2.6743 no . . C12 H1 3.08(8) no . . C13 H9 3.2817 no . . C13 H11 3.2641 no . . C14 H11 2.5922 no . . C15 H17 3.2428 no . . C15 H19 3.3159 no . . C16 H18 3.2580 no . . C17 H19 3.2856 no . . C18 H16 3.2695 no . . C19 H17 3.2700 no . . C20 H16 3.2765 no . . C20 H18 3.2340 no . . C21 H11 2.5168 no . . H3 H4 2.3287 no . . H4 H5 2.3247 no . . H5 H6 2.3353 no . . H11 H21A 2.3994 no . . H11 H21B 3.4849 no . . H11 H21C 2.2156 no . . H16 H17 2.3228 no . . H17 H18 2.3259 no . . H18 H19 2.3370 no . . S1 H6 3.4924 no . 7_575 S2 H19 3.0642 no . 3_565 O1 H18 3.2718 no . 3_565 O1 H19 2.6850 no . 3_565 O1 H19 2.8662 no . 3_575 O2 H5 3.5191 no . 7_565 O2 H6 2.8498 no . 7_565 O2 H9 3.5932 no . 1_545 O2 H16 3.1046 no . 6_555 O2 H21B 3.3358 no . 1_565 O2 H21C 2.8655 no . 1_565 N1 H18 3.0135 no . 3_565 N2 H21A 3.1397 no . 6_545 N2 H21A 3.2932 no . 6_555 N2 H21B 2.5718 no . 6_555 N2 H21C 3.4080 no . 6_555 C2 H18 3.4575 no . 3_565 C3 H18 3.3037 no . 3_565 C3 H18 3.0273 no . 3_575 C4 H17 3.0498 no . 4_564 C4 H17 3.2791 no . 4_574 C5 H16 3.5151 no . 4_564 C5 H16 3.5208 no . 4_574 C5 H17 3.2141 no . 4_564 C5 H17 3.3781 no . 4_574 C6 H9 3.4206 no . 7_565 C6 H9 3.5346 no . 7_575 C9 H6 3.3338 no . 7_565 C9 H6 3.5047 no . 7_575 C9 H21C 3.4598 no . 1_565 C10 H6 3.5201 no . 7_565 C10 H21C 2.8009 no . 1_565 C11 H11 3.5757 no . 1_565 C11 H21A 3.5198 no . 6_555 C11 H21C 3.0465 no . 1_565 C12 H11 3.5917 no . 1_565 C13 H19 3.5671 no . 3_565 C14 H21B 3.5093 no . 6_555 C15 H16 3.4342 no . 1_565 C15 H21B 2.9369 no . 6_555 C16 H5 2.8805 no . 4_575 C16 H21B 3.2455 no . 6_545 C16 H21B 3.0349 no . 6_555 C17 H3 3.5057 no . 3_565 C17 H4 3.1276 no . 4_575 C17 H5 3.0132 no . 4_575 C17 H17 3.5430 no . 1_565 C18 H1 3.14(6) no . 3_565 C18 H3 3.3603 no . 3_565 C18 H3 3.0333 no . 3_575 C18 H17 3.4579 no . 1_565 C18 H19 3.4069 no . 1_545 C19 H1 3.18(8) no . 3_565 C19 H1 3.52(8) no . 3_575 C19 H19 3.5993 no . 1_545 C21 H11 3.2688 no . 6_545 C21 H16 3.0026 no . 6_555 C21 H21A 3.2625 no . 1_545 C21 H21C 3.1708 no . 1_565 H1 C18 3.14(6) no . 3_565 H1 C19 3.18(8) no . 3_565 H1 C19 3.52(8) no . 3_575 H1 H18 2.6943 no . 3_565 H1 H19 2.8048 no . 3_565 H1 H19 2.7353 no . 3_575 H3 C17 3.5057 no . 3_565 H3 C18 3.3603 no . 3_565 H3 C18 3.0333 no . 3_575 H3 H4 2.9919 no . 2_554 H3 H17 3.0212 no . 3_565 H3 H18 2.7231 no . 3_565 H3 H18 2.4295 no . 3_575 H4 C17 3.1276 no . 4_574 H4 H3 2.9919 no . 2_554 H4 H4 2.9985 no . 2_554 H4 H17 2.7515 no . 4_564 H4 H17 2.6603 no . 4_574 H4 H18 3.5804 no . 4_574 H5 O2 3.5191 no . 7_565 H5 C16 2.8805 no . 4_574 H5 C17 3.0132 no . 4_574 H5 H16 3.0088 no . 4_564 H5 H16 2.6184 no . 4_574 H5 H17 3.0502 no . 4_564 H5 H17 2.8543 no . 4_574 H5 H21B 3.0895 no . 7_565 H6 S1 3.4924 no . 7_575 H6 O2 2.8498 no . 7_565 H6 C9 3.3338 no . 7_565 H6 C9 3.5047 no . 7_575 H6 C10 3.5201 no . 7_565 H6 H9 2.6948 no . 7_565 H6 H9 2.7943 no . 7_575 H9 O2 3.5932 no . 1_565 H9 C6 3.4206 no . 7_565 H9 C6 3.5346 no . 7_575 H9 H6 2.6948 no . 7_565 H9 H6 2.7943 no . 7_575 H11 C11 3.5757 no . 1_545 H11 C12 3.5917 no . 1_545 H11 C21 3.2688 no . 6_555 H11 H21A 2.8716 no . 6_545 H11 H21A 3.0274 no . 6_555 H11 H21B 3.3060 no . 6_555 H11 H21C 3.1432 no . 1_565 H11 H21C 2.9335 no . 6_555 H16 O2 3.1046 no . 6_545 H16 C5 3.5151 no . 4_565 H16 C5 3.5208 no . 4_575 H16 C15 3.4342 no . 1_545 H16 C21 3.0026 no . 6_545 H16 H5 3.0088 no . 4_565 H16 H5 2.6184 no . 4_575 H16 H21A 3.0448 no . 6_545 H16 H21B 2.4838 no . 6_545 H16 H21B 2.7327 no . 6_555 H17 C4 3.0498 no . 4_565 H17 C4 3.2791 no . 4_575 H17 C5 3.2141 no . 4_565 H17 C5 3.3781 no . 4_575 H17 C17 3.5430 no . 1_545 H17 C18 3.4579 no . 1_545 H17 H3 3.0212 no . 3_565 H17 H4 2.7515 no . 4_565 H17 H4 2.6603 no . 4_575 H17 H5 3.0502 no . 4_565 H17 H5 2.8543 no . 4_575 H18 O1 3.2718 no . 3_565 H18 N1 3.0135 no . 3_565 H18 C2 3.4575 no . 3_565 H18 C3 3.3037 no . 3_565 H18 C3 3.0273 no . 3_575 H18 H1 2.6943 no . 3_565 H18 H3 2.7231 no . 3_565 H18 H3 2.4295 no . 3_575 H18 H4 3.5804 no . 4_575 H18 H19 3.5101 no . 1_545 H19 S2 3.0642 no . 3_565 H19 O1 2.6850 no . 3_565 H19 O1 2.8662 no . 3_575 H19 C13 3.5671 no . 3_565 H19 C18 3.4069 no . 1_565 H19 C19 3.5993 no . 1_565 H19 H1 2.8048 no . 3_565 H19 H1 2.7353 no . 3_575 H19 H18 3.5101 no . 1_565 H21A N2 3.2932 no . 6_545 H21A N2 3.1397 no . 6_555 H21A C11 3.5198 no . 6_545 H21A C21 3.2625 no . 1_565 H21A H11 3.0274 no . 6_545 H21A H11 2.8716 no . 6_555 H21A H16 3.0448 no . 6_555 H21A H21A 3.5423 no . 6_545 H21A H21A 3.5423 no . 6_555 H21A H21B 3.0871 no . 1_565 H21A H21C 2.5715 no . 1_565 H21A H21C 3.0406 no . 6_555 H21B O2 3.3358 no . 1_545 H21B N2 2.5718 no . 6_545 H21B C14 3.5093 no . 6_545 H21B C15 2.9369 no . 6_545 H21B C16 3.0349 no . 6_545 H21B C16 3.2455 no . 6_555 H21B H5 3.0895 no . 7_565 H21B H11 3.3060 no . 6_545 H21B H16 2.7327 no . 6_545 H21B H16 2.4838 no . 6_555 H21B H21A 3.0871 no . 1_545 H21C O2 2.8655 no . 1_545 H21C N2 3.4080 no . 6_545 H21C C9 3.4598 no . 1_545 H21C C10 2.8009 no . 1_545 H21C C11 3.0465 no . 1_545 H21C C21 3.1708 no . 1_545 H21C H11 3.1432 no . 1_545 H21C H11 2.9335 no . 6_545 H21C H21A 2.5715 no . 1_545 H21C H21A 3.0406 no . 6_545 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 N1 . . . 2.603(10) 0.907 1.76(11) 153(6) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 966982' data_General _audit_creation_date 2013-07-12 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Ken-ichi Sakai' _publ_contact_author_email k-sakai@photon.chitose.ac.jp _publ_contact_author_fax +81-123-27-6054 _publ_contact_author_phone +81-123-27-6054 _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal CrystEngComm _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name 'Ken-ichi Sakai' 'Hiroshi Kawamura' 'Takaaki Ishikawa' 'Noriyuki Kobayashi' 'Chiori Ikeda' 'Takemitsu Kikuchi' 'Tomoyuki Akutagawa' #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, D. Siliqi, R. Spagna (2007) SIR2008 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_2,6-bis(benzothiazol-2-yl)-4-propoxyphenol #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H18 N2 O2 S2' _chemical_formula_moiety 'C23 H18 N2 O2 S2' _chemical_formula_weight 418.53 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.7301(2) _cell_length_b 22.2883(4) _cell_length_c 7.47946(10) _cell_angle_alpha 90.0000 _cell_angle_beta 100.4380 _cell_angle_gamma 90.0000 _cell_volume 1923.10(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6499 _cell_measurement_theta_min 3.83 _cell_measurement_theta_max 68.22 _cell_measurement_temperature 100 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yello _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872.00 _exptl_absorpt_coefficient_mu 2.698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 0.764 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 21553 _diffrn_reflns_av_R_equivalents 0.0906 _diffrn_reflns_theta_max 68.21 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3476 _reflns_number_gt 2653 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1563 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3476 _refine_ls_number_parameters 266 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.390 _refine_diff_density_min -0.430 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.3331 0.5567 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.08451(6) 0.06426(3) 0.02873(10) 0.0299(3) Uani 1.0 4 d . . . S2 S 0.24571(6) 0.32867(3) 0.33663(11) 0.0304(3) Uani 1.0 4 d . . . O1 O -0.18541(18) 0.34773(9) -0.0436(3) 0.0321(6) Uani 1.0 4 d . . . O2 O 0.06954(19) 0.14593(9) 0.1993(3) 0.0302(6) Uani 1.0 4 d . . . N1 N -0.2668(2) 0.12963(10) -0.0875(4) 0.0288(6) Uani 1.0 4 d . . . N2 N 0.2430(2) 0.21231(11) 0.3401(4) 0.0270(6) Uani 1.0 4 d . . . C1 C -0.1580(3) 0.13356(13) -0.0078(4) 0.0275(7) Uani 1.0 4 d . . . C2 C -0.2987(3) 0.07053(13) -0.1237(5) 0.0315(8) Uani 1.0 4 d . . . C3 C -0.4100(3) 0.05126(14) -0.2055(5) 0.0372(8) Uani 1.0 4 d . . . C4 C -0.4301(3) -0.00906(14) -0.2337(5) 0.0397(8) Uani 1.0 4 d . . . C5 C -0.3410(3) -0.05101(14) -0.1813(5) 0.0395(9) Uani 1.0 4 d . . . C6 C -0.2314(3) -0.03338(14) -0.0993(5) 0.0357(8) Uani 1.0 4 d . . . C7 C -0.2106(3) 0.02810(13) -0.0709(4) 0.0295(7) Uani 1.0 4 d . . . C8 C 0.0112(3) 0.19692(12) 0.1419(4) 0.0265(7) Uani 1.0 4 d . . . C9 C -0.1013(3) 0.19179(13) 0.0413(4) 0.0259(7) Uani 1.0 4 d . . . C10 C -0.1639(3) 0.24370(13) -0.0173(4) 0.0286(7) Uani 1.0 4 d . . . C11 C -0.1150(3) 0.30030(13) 0.0218(5) 0.0295(7) Uani 1.0 4 d . . . C12 C -0.0040(3) 0.30542(12) 0.1188(4) 0.0266(7) Uani 1.0 4 d . . . C13 C 0.0612(3) 0.25422(12) 0.1812(4) 0.0262(7) Uani 1.0 4 d . . . C14 C 0.1784(3) 0.25908(12) 0.2819(4) 0.0266(7) Uani 1.0 4 d . . . C15 C 0.3520(3) 0.22951(13) 0.4309(4) 0.0285(7) Uani 1.0 4 d . . . C16 C 0.4411(3) 0.19068(14) 0.5085(4) 0.0315(8) Uani 1.0 4 d . . . C17 C 0.5452(3) 0.21462(14) 0.5941(5) 0.0351(8) Uani 1.0 4 d . . . C18 C 0.5619(3) 0.27662(14) 0.6049(5) 0.0345(8) Uani 1.0 4 d . . . C19 C 0.4758(3) 0.31569(14) 0.5299(5) 0.0329(8) Uani 1.0 4 d . . . C20 C 0.3705(3) 0.29177(13) 0.4437(4) 0.0294(7) Uani 1.0 4 d . . . C21 C -0.1384(3) 0.40686(12) -0.0108(5) 0.0316(7) Uani 1.0 4 d . . . C22 C -0.2322(3) 0.45103(14) -0.0889(5) 0.0362(8) Uani 1.0 4 d . . . C23 C -0.1852(4) 0.51566(14) -0.0756(5) 0.0492(10) Uani 1.0 4 d . . . H1 H 0.133(4) 0.1566(16) 0.256(6) 0.067(14) Uiso 1.0 4 d . . . H3 H -0.4705 0.0795 -0.2409 0.0446 Uiso 1.0 4 calc R . . H4 H -0.5051 -0.0225 -0.2892 0.0476 Uiso 1.0 4 calc R . . H5 H -0.3566 -0.0925 -0.2029 0.0474 Uiso 1.0 4 calc R . . H6 H -0.1718 -0.0620 -0.0630 0.0428 Uiso 1.0 4 calc R . . H10 H -0.2405 0.2404 -0.0846 0.0343 Uiso 1.0 4 calc R . . H12 H 0.0290 0.3441 0.1441 0.0320 Uiso 1.0 4 calc R . . H16 H 0.4301 0.1485 0.5022 0.0378 Uiso 1.0 4 calc R . . H17 H 0.6063 0.1886 0.6463 0.0421 Uiso 1.0 4 calc R . . H18 H 0.6342 0.2921 0.6653 0.0414 Uiso 1.0 4 calc R . . H19 H 0.4877 0.3579 0.5366 0.0395 Uiso 1.0 4 calc R . . H21A H -0.0701 0.4119 -0.0701 0.0379 Uiso 1.0 4 calc R . . H21B H -0.1139 0.4137 0.1213 0.0379 Uiso 1.0 4 calc R . . H22A H -0.2974 0.4479 -0.0217 0.0434 Uiso 1.0 4 calc R . . H22B H -0.2620 0.4410 -0.2178 0.0434 Uiso 1.0 4 calc R . . H23A H -0.1146 0.5175 -0.1281 0.0591 Uiso 1.0 4 calc R . . H23B H -0.1674 0.5279 0.0523 0.0591 Uiso 1.0 4 calc R . . H23C H -0.2437 0.5427 -0.1424 0.0591 Uiso 1.0 4 calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0244(5) 0.0297(5) 0.0335(5) 0.0005(3) -0.0002(4) 0.0001(3) S2 0.0239(5) 0.0305(5) 0.0341(5) -0.0005(3) -0.0018(4) -0.0000(3) O1 0.0276(13) 0.0288(12) 0.0365(13) 0.0041(9) -0.0034(10) 0.0038(9) O2 0.0222(13) 0.0280(12) 0.0365(13) 0.0021(9) -0.0052(10) 0.0020(9) N1 0.0237(14) 0.0299(14) 0.0308(15) -0.0003(11) -0.0001(11) -0.0002(11) N2 0.0226(14) 0.0327(14) 0.0239(14) 0.0013(10) -0.0008(11) 0.0018(11) C1 0.0280(17) 0.0287(16) 0.0242(16) 0.0020(12) 0.0008(13) 0.0014(12) C2 0.0295(18) 0.0381(18) 0.0255(18) -0.0018(14) 0.0013(14) -0.0013(14) C3 0.0283(18) 0.0391(18) 0.042(2) -0.0030(14) 0.0006(15) 0.0004(15) C4 0.0293(18) 0.048(2) 0.039(2) -0.0072(15) -0.0000(15) -0.0015(16) C5 0.041(2) 0.0363(18) 0.042(3) -0.0094(15) 0.0085(17) -0.0055(15) C6 0.0350(19) 0.0320(18) 0.039(2) 0.0004(14) 0.0049(16) -0.0019(14) C7 0.0261(17) 0.0347(17) 0.0271(18) -0.0031(13) 0.0027(14) -0.0017(13) C8 0.0274(17) 0.0277(16) 0.0237(17) 0.0022(12) 0.0027(13) 0.0014(12) C9 0.0211(16) 0.0319(16) 0.0233(17) -0.0006(12) 0.0006(13) 0.0003(13) C10 0.0225(17) 0.0341(17) 0.0283(18) 0.0031(12) 0.0023(14) 0.0035(13) C11 0.0278(17) 0.0320(17) 0.0285(18) 0.0039(13) 0.0051(14) 0.0028(13) C12 0.0253(17) 0.0274(16) 0.0255(17) 0.0001(12) -0.0001(13) 0.0005(12) C13 0.0250(17) 0.0289(16) 0.0243(17) 0.0005(12) 0.0030(13) -0.0004(12) C14 0.0243(17) 0.0300(16) 0.0253(17) -0.0007(12) 0.0037(13) 0.0004(12) C15 0.0223(16) 0.0373(18) 0.0253(17) 0.0021(13) 0.0024(13) 0.0011(13) C16 0.0270(18) 0.0386(18) 0.0274(18) 0.0044(13) 0.0011(14) 0.0036(14) C17 0.0262(18) 0.046(2) 0.0301(19) 0.0047(14) -0.0018(14) 0.0044(15) C18 0.0245(17) 0.049(2) 0.0294(19) -0.0034(14) 0.0022(14) -0.0001(15) C19 0.0260(18) 0.0415(18) 0.0301(19) -0.0039(14) 0.0020(14) -0.0006(14) C20 0.0248(17) 0.0351(17) 0.0273(18) 0.0017(13) 0.0025(13) -0.0002(13) C21 0.0319(18) 0.0279(16) 0.0337(19) 0.0026(13) 0.0027(14) 0.0021(14) C22 0.035(2) 0.0390(19) 0.035(2) 0.0106(15) 0.0081(15) 0.0068(15) C23 0.067(3) 0.0320(19) 0.050(3) 0.0139(17) 0.013(2) 0.0050(16) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C1 1.766(3) yes . . S1 C7 1.730(3) yes . . S2 C14 1.755(3) yes . . S2 C20 1.743(3) yes . . O1 C11 1.376(4) yes . . O1 C21 1.432(4) yes . . O2 C8 1.356(4) yes . . N1 C1 1.310(4) yes . . N1 C2 1.383(4) yes . . N2 C14 1.315(4) yes . . N2 C15 1.389(4) yes . . C1 C9 1.474(4) yes . . C2 C3 1.404(5) yes . . C2 C7 1.404(4) yes . . C3 C4 1.375(5) yes . . C4 C5 1.404(5) yes . . C5 C6 1.377(5) yes . . C6 C7 1.401(5) yes . . C8 C9 1.400(4) yes . . C8 C13 1.414(4) yes . . C9 C10 1.398(4) yes . . C10 C11 1.395(4) yes . . C11 C12 1.375(4) yes . . C12 C13 1.406(4) yes . . C13 C14 1.447(4) yes . . C15 C16 1.400(4) yes . . C15 C20 1.405(4) yes . . C16 C17 1.379(5) yes . . C17 C18 1.396(5) yes . . C18 C19 1.375(5) yes . . C19 C20 1.391(5) yes . . C21 C22 1.512(5) yes . . C22 C23 1.539(5) yes . . O2 H1 0.83(4) no . . C3 H3 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C10 H10 0.950 no . . C12 H12 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C21 H21A 0.990 no . . C21 H21B 0.990 no . . C22 H22A 0.990 no . . C22 H22B 0.990 no . . C23 H23A 0.980 no . . C23 H23B 0.980 no . . C23 H23C 0.980 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 S1 C7 89.17(14) yes . . . C14 S2 C20 89.71(14) yes . . . C11 O1 C21 117.3(3) yes . . . C1 N1 C2 111.1(3) yes . . . C14 N2 C15 111.5(3) yes . . . S1 C1 N1 114.8(2) yes . . . S1 C1 C9 123.1(3) yes . . . N1 C1 C9 122.0(3) yes . . . N1 C2 C3 125.0(3) yes . . . N1 C2 C7 115.3(3) yes . . . C3 C2 C7 119.7(3) yes . . . C2 C3 C4 119.1(3) yes . . . C3 C4 C5 120.6(3) yes . . . C4 C5 C6 121.4(3) yes . . . C5 C6 C7 118.0(3) yes . . . S1 C7 C2 109.6(3) yes . . . S1 C7 C6 129.2(3) yes . . . C2 C7 C6 121.1(3) yes . . . O2 C8 C9 118.3(3) yes . . . O2 C8 C13 121.6(3) yes . . . C9 C8 C13 120.1(3) yes . . . C1 C9 C8 123.0(3) yes . . . C1 C9 C10 117.6(3) yes . . . C8 C9 C10 119.4(3) yes . . . C9 C10 C11 120.7(3) yes . . . O1 C11 C10 115.0(3) yes . . . O1 C11 C12 125.0(3) yes . . . C10 C11 C12 120.0(3) yes . . . C11 C12 C13 120.9(3) yes . . . C8 C13 C12 118.9(3) yes . . . C8 C13 C14 119.7(3) yes . . . C12 C13 C14 121.4(3) yes . . . S2 C14 N2 114.6(2) yes . . . S2 C14 C13 122.2(2) yes . . . N2 C14 C13 123.3(3) yes . . . N2 C15 C16 125.8(3) yes . . . N2 C15 C20 115.0(3) yes . . . C16 C15 C20 119.2(3) yes . . . C15 C16 C17 119.0(3) yes . . . C16 C17 C18 120.9(3) yes . . . C17 C18 C19 121.2(3) yes . . . C18 C19 C20 118.1(3) yes . . . S2 C20 C15 109.2(2) yes . . . S2 C20 C19 129.3(3) yes . . . C15 C20 C19 121.6(3) yes . . . O1 C21 C22 107.6(3) yes . . . C21 C22 C23 110.9(3) yes . . . C8 O2 H1 106(3) no . . . C2 C3 H3 120.453 no . . . C4 C3 H3 120.447 no . . . C3 C4 H4 119.668 no . . . C5 C4 H4 119.685 no . . . C4 C5 H5 119.273 no . . . C6 C5 H5 119.278 no . . . C5 C6 H6 121.014 no . . . C7 C6 H6 121.006 no . . . C9 C10 H10 119.663 no . . . C11 C10 H10 119.655 no . . . C11 C12 H12 119.534 no . . . C13 C12 H12 119.530 no . . . C15 C16 H16 120.486 no . . . C17 C16 H16 120.489 no . . . C16 C17 H17 119.552 no . . . C18 C17 H17 119.553 no . . . C17 C18 H18 119.406 no . . . C19 C18 H18 119.408 no . . . C18 C19 H19 120.926 no . . . C20 C19 H19 120.931 no . . . O1 C21 H21A 110.195 no . . . O1 C21 H21B 110.188 no . . . C22 C21 H21A 110.181 no . . . C22 C21 H21B 110.181 no . . . H21A C21 H21B 108.484 no . . . C21 C22 H22A 109.445 no . . . C21 C22 H22B 109.452 no . . . C23 C22 H22A 109.463 no . . . C23 C22 H22B 109.455 no . . . H22A C22 H22B 108.044 no . . . C22 C23 H23A 109.467 no . . . C22 C23 H23B 109.465 no . . . C22 C23 H23C 109.463 no . . . H23A C23 H23B 109.472 no . . . H23A C23 H23C 109.474 no . . . H23B C23 H23C 109.486 no . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 S1 C7 C2 -0.2(2) no . . . . C1 S1 C7 C6 -179.5(3) no . . . . C7 S1 C1 N1 -0.1(3) no . . . . C7 S1 C1 C9 -178.2(3) no . . . . C14 S2 C20 C15 -0.3(2) no . . . . C14 S2 C20 C19 179.2(3) no . . . . C20 S2 C14 N2 0.6(3) no . . . . C20 S2 C14 C13 -179.5(3) no . . . . C11 O1 C21 C22 -178.1(3) no . . . . C21 O1 C11 C10 -178.6(3) no . . . . C21 O1 C11 C12 1.3(5) no . . . . C1 N1 C2 C3 178.9(3) no . . . . C1 N1 C2 C7 -0.5(4) no . . . . C2 N1 C1 S1 0.3(4) no . . . . C2 N1 C1 C9 178.5(3) no . . . . C14 N2 C15 C16 -179.7(3) no . . . . C14 N2 C15 C20 0.6(4) no . . . . C15 N2 C14 S2 -0.8(4) no . . . . C15 N2 C14 C13 179.3(3) no . . . . S1 C1 C9 C8 -8.4(5) no . . . . S1 C1 C9 C10 171.20(19) no . . . . N1 C1 C9 C8 173.6(3) no . . . . N1 C1 C9 C10 -6.7(5) no . . . . N1 C2 C3 C4 -180.0(3) no . . . . N1 C2 C7 S1 0.5(4) no . . . . N1 C2 C7 C6 179.8(3) no . . . . C3 C2 C7 S1 -179.0(3) no . . . . C3 C2 C7 C6 0.3(5) no . . . . C7 C2 C3 C4 -0.5(5) no . . . . C2 C3 C4 C5 0.1(5) no . . . . C3 C4 C5 C6 0.5(6) no . . . . C4 C5 C6 C7 -0.7(5) no . . . . C5 C6 C7 S1 179.5(3) no . . . . C5 C6 C7 C2 0.2(5) no . . . . O2 C8 C9 C1 -1.3(5) no . . . . O2 C8 C9 C10 179.1(3) no . . . . O2 C8 C13 C12 -179.6(3) no . . . . O2 C8 C13 C14 1.2(5) no . . . . C9 C8 C13 C12 0.5(5) no . . . . C9 C8 C13 C14 -178.7(3) no . . . . C13 C8 C9 C1 178.7(3) no . . . . C13 C8 C9 C10 -0.9(5) no . . . . C1 C9 C10 C11 -179.0(3) no . . . . C8 C9 C10 C11 0.6(5) no . . . . C9 C10 C11 O1 180.0(3) no . . . . C9 C10 C11 C12 0.1(5) no . . . . O1 C11 C12 C13 179.6(3) no . . . . C10 C11 C12 C13 -0.5(5) no . . . . C11 C12 C13 C8 0.2(5) no . . . . C11 C12 C13 C14 179.4(3) no . . . . C8 C13 C14 S2 -179.6(3) no . . . . C8 C13 C14 N2 0.3(5) no . . . . C12 C13 C14 S2 1.2(5) no . . . . C12 C13 C14 N2 -178.9(3) no . . . . N2 C15 C16 C17 179.8(3) no . . . . N2 C15 C20 S2 -0.1(4) no . . . . N2 C15 C20 C19 -179.6(3) no . . . . C16 C15 C20 S2 -179.8(3) no . . . . C16 C15 C20 C19 0.7(5) no . . . . C20 C15 C16 C17 -0.5(5) no . . . . C15 C16 C17 C18 0.4(5) no . . . . C16 C17 C18 C19 -0.4(5) no . . . . C17 C18 C19 C20 0.6(5) no . . . . C18 C19 C20 S2 179.9(3) no . . . . C18 C19 C20 C15 -0.7(5) no . . . . O1 C21 C22 C23 -174.6(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 O2 2.715(3) no . . S1 C8 3.221(3) no . . S2 C12 3.127(3) no . . O2 N2 2.581(3) no . . O2 C1 2.846(4) no . . O2 C14 2.844(4) no . . N1 C10 2.823(4) no . . N2 C8 2.872(4) no . . C1 C3 3.564(5) no . . C2 C5 2.774(5) no . . C3 C6 2.824(5) no . . C4 C7 2.768(5) no . . C8 C11 2.797(4) no . . C9 C12 2.795(4) no . . C10 C13 2.795(4) no . . C12 C21 2.826(4) no . . C14 C16 3.578(4) no . . C15 C18 2.775(4) no . . C16 C19 2.816(5) no . . C17 C20 2.754(5) no . . S1 S1 3.5538(10) no . 3_555 O1 C1 3.569(4) no . 4_554 O1 C9 3.535(4) no . 4_554 O2 C6 3.313(4) no . 3_555 O2 C12 3.570(4) no . 4_555 N1 C17 3.496(4) no . 1_454 N1 C18 3.395(5) no . 4_454 N1 C19 3.512(5) no . 4_454 N2 C14 3.579(4) no . 4_555 N2 C20 3.556(5) no . 4_554 C1 O1 3.569(4) no . 4_555 C6 O2 3.313(4) no . 3_555 C8 C11 3.434(5) no . 4_555 C9 O1 3.535(4) no . 4_555 C9 C12 3.549(5) no . 4_554 C10 C18 3.529(5) no . 4_454 C11 C8 3.434(5) no . 4_554 C12 O2 3.570(4) no . 4_554 C12 C9 3.549(5) no . 4_555 C13 C14 3.519(5) no . 4_554 C14 N2 3.579(4) no . 4_554 C14 C13 3.519(5) no . 4_555 C16 C20 3.523(5) no . 4_555 C17 N1 3.496(4) no . 1_656 C17 C19 3.564(5) no . 4_555 C18 N1 3.395(5) no . 4_655 C18 C10 3.529(5) no . 4_655 C19 N1 3.512(5) no . 4_655 C19 C17 3.564(5) no . 4_554 C20 N2 3.556(5) no . 4_555 C20 C16 3.523(5) no . 4_554 S1 H1 3.48(4) no . . S1 H6 3.0309 no . . S2 H12 2.7074 no . . S2 H19 3.0301 no . . O1 H10 2.4824 no . . O1 H12 2.6498 no . . O1 H22A 2.6106 no . . O1 H22B 2.5307 no . . N1 H3 2.6978 no . . N1 H10 2.4877 no . . N2 H1 1.82(4) no . . N2 H16 2.7109 no . . C1 H10 2.5953 no . . C2 H4 3.2561 no . . C2 H6 3.3029 no . . C3 H5 3.2632 no . . C4 H6 3.2873 no . . C5 H3 3.2747 no . . C6 H4 3.2752 no . . C7 H3 3.2886 no . . C7 H5 3.2428 no . . C8 H10 3.2726 no . . C8 H12 3.2869 no . . C9 H1 3.03(4) no . . C10 H12 3.2544 no . . C11 H21A 2.6582 no . . C11 H21B 2.6336 no . . C12 H10 3.2524 no . . C12 H21A 2.7983 no . . C12 H21B 2.7370 no . . C13 H1 2.37(4) no . . C14 H1 2.35(4) no . . C14 H12 2.6594 no . . C15 H1 3.12(4) no . . C15 H17 3.2539 no . . C15 H19 3.2995 no . . C16 H18 3.2637 no . . C17 H19 3.2749 no . . C18 H16 3.2730 no . . C19 H17 3.2632 no . . C20 H16 3.2822 no . . C20 H18 3.2337 no . . C21 H12 2.5161 no . . C21 H23A 2.6502 no . . C21 H23B 2.7692 no . . C21 H23C 3.3497 no . . C23 H21A 2.6746 no . . C23 H21B 2.7548 no . . H3 H4 2.3263 no . . H4 H5 2.3393 no . . H5 H6 2.3316 no . . H12 H21A 2.3504 no . . H12 H21B 2.2668 no . . H16 H17 2.3296 no . . H17 H18 2.3311 no . . H18 H19 2.3297 no . . H21A H22A 2.8690 no . . H21A H22B 2.4103 no . . H21A H23A 2.4341 no . . H21A H23B 3.0329 no . . H21A H23C 3.5415 no . . H21B H22A 2.3501 no . . H21B H22B 2.8684 no . . H21B H23A 2.9727 no . . H21B H23B 2.6492 no . . H22A H23A 2.8734 no . . H22A H23B 2.3451 no . . H22A H23C 2.4250 no . . H22B H23A 2.4351 no . . H22B H23B 2.8720 no . . H22B H23C 2.3361 no . . S1 H6 2.9706 no . 3_555 S1 H21A 3.0220 no . 4_555 S1 H21B 3.0438 no . 4_554 S1 H22B 3.0615 no . 4_555 S1 H23A 3.2193 no . 4_555 S2 H5 3.3161 no . 2_555 S2 H6 3.1759 no . 2_555 S2 H23C 3.2119 no . 3_565 O1 H17 3.1463 no . 4_454 O1 H18 3.0142 no . 1_454 O2 H5 3.5679 no . 3_555 O2 H6 2.5332 no . 3_555 O2 H12 3.4522 no . 4_555 O2 H21A 2.8883 no . 4_555 O2 H23B 3.3046 no . 2_545 N1 H17 2.6134 no . 1_454 N1 H18 2.9608 no . 4_454 N1 H19 3.1938 no . 4_454 N1 H21B 3.2098 no . 4_554 N1 H22B 3.1738 no . 4_555 N2 H5 3.2346 no . 3_555 C1 H18 3.3930 no . 4_454 C1 H21A 3.4041 no . 4_555 C1 H21B 3.0962 no . 4_554 C1 H22B 3.1493 no . 4_555 C2 H17 3.2290 no . 1_454 C2 H19 3.3687 no . 4_454 C2 H21B 3.1556 no . 4_554 C2 H22A 3.0082 no . 4_554 C2 H22B 2.9990 no . 4_555 C3 H16 3.3919 no . 1_454 C3 H17 3.2721 no . 1_454 C3 H19 3.1002 no . 4_454 C3 H22A 2.9105 no . 4_554 C4 H4 3.5808 no . 3_454 C4 H19 3.4337 no . 2_545 C4 H22A 3.5166 no . 2_444 C4 H22A 3.1840 no . 4_554 C5 H1 3.50(4) no . 3_555 C5 H16 3.2651 no . 3_555 C5 H19 2.9892 no . 2_545 C5 H22A 3.5351 no . 4_554 C5 H23B 3.1392 no . 4_554 C6 H1 3.28(4) no . 3_555 C6 H22B 3.5884 no . 4_555 C6 H23A 3.5595 no . 4_555 C6 H23B 2.8425 no . 4_554 C6 H23C 3.4521 no . 4_555 C7 H21B 3.0357 no . 4_554 C7 H22A 3.3833 no . 4_554 C7 H22B 2.8962 no . 4_555 C7 H23A 3.4526 no . 4_555 C7 H23B 3.2049 no . 4_554 C8 H21A 3.4893 no . 4_555 C9 H18 3.4146 no . 4_454 C10 H10 3.5305 no . 4_555 C10 H17 3.5563 no . 1_454 C10 H17 3.4987 no . 4_454 C10 H18 3.2203 no . 1_454 C10 H18 3.0475 no . 4_454 C11 H17 3.5667 no . 4_454 C11 H18 3.5994 no . 1_454 C12 H1 3.50(5) no . 4_554 C15 H5 3.5036 no . 3_555 C16 H3 3.1661 no . 1_656 C16 H5 3.1902 no . 3_555 C17 H3 3.2721 no . 1_656 C17 H10 3.1996 no . 1_656 C17 H10 3.2136 no . 4_655 C17 H18 3.5508 no . 4_554 C18 H10 3.0764 no . 1_656 C18 H10 2.9520 no . 4_655 C19 H3 3.2274 no . 4_655 C19 H5 2.9110 no . 2_555 C19 H17 3.4891 no . 4_554 C20 H5 3.2494 no . 2_555 C21 H23A 3.4073 no . 3_565 C22 H4 3.1081 no . 2_454 C23 H21A 3.4028 no . 3_565 H1 C5 3.50(4) no . 3_555 H1 C6 3.28(4) no . 3_555 H1 C12 3.50(5) no . 4_555 H1 H5 3.0721 no . 3_555 H1 H6 2.6402 no . 3_555 H1 H12 3.3461 no . 4_555 H1 H21A 3.2913 no . 4_555 H1 H23B 3.1980 no . 2_545 H3 C16 3.1661 no . 1_454 H3 C17 3.2721 no . 1_454 H3 C19 3.2274 no . 4_454 H3 H16 2.5693 no . 1_454 H3 H17 2.7759 no . 1_454 H3 H19 2.6202 no . 4_454 H3 H22A 3.2334 no . 4_554 H3 H23C 3.4084 no . 2_444 H4 C4 3.5808 no . 3_454 H4 C22 3.1081 no . 2_444 H4 H4 3.3312 no . 3_454 H4 H16 3.4206 no . 3_555 H4 H19 3.2534 no . 2_545 H4 H22A 2.5728 no . 2_444 H4 H22B 2.8605 no . 2_444 H4 H23C 3.2425 no . 2_444 H5 S2 3.3161 no . 2_545 H5 O2 3.5679 no . 3_555 H5 N2 3.2346 no . 3_555 H5 C15 3.5036 no . 3_555 H5 C16 3.1902 no . 3_555 H5 C19 2.9110 no . 2_545 H5 C20 3.2494 no . 2_545 H5 H1 3.0721 no . 3_555 H5 H16 2.5715 no . 3_555 H5 H19 2.4148 no . 2_545 H5 H23B 3.4391 no . 4_554 H6 S1 2.9706 no . 3_555 H6 S2 3.1759 no . 2_545 H6 O2 2.5332 no . 3_555 H6 H1 2.6402 no . 3_555 H6 H23A 3.3499 no . 4_555 H6 H23B 2.9857 no . 4_554 H6 H23C 3.4285 no . 4_555 H10 C10 3.5305 no . 4_554 H10 C17 3.1996 no . 1_454 H10 C17 3.2136 no . 4_454 H10 C18 3.0764 no . 1_454 H10 C18 2.9520 no . 4_454 H10 H17 2.7025 no . 1_454 H10 H17 3.1374 no . 4_454 H10 H18 2.4475 no . 1_454 H10 H18 2.6786 no . 4_454 H12 O2 3.4522 no . 4_554 H12 H1 3.3461 no . 4_554 H12 H23A 3.2520 no . 3_565 H12 H23C 3.5667 no . 3_565 H16 C3 3.3919 no . 1_656 H16 C5 3.2651 no . 3_555 H16 H3 2.5693 no . 1_656 H16 H4 3.4206 no . 3_555 H16 H5 2.5715 no . 3_555 H16 H23C 3.5023 no . 2_545 H17 O1 3.1463 no . 4_655 H17 N1 2.6134 no . 1_656 H17 C2 3.2290 no . 1_656 H17 C3 3.2721 no . 1_656 H17 C10 3.5563 no . 1_656 H17 C10 3.4987 no . 4_655 H17 C11 3.5667 no . 4_655 H17 C19 3.4891 no . 4_555 H17 H3 2.7759 no . 1_656 H17 H10 2.7025 no . 1_656 H17 H10 3.1374 no . 4_655 H17 H22A 3.5534 no . 4_655 H18 O1 3.0142 no . 1_656 H18 N1 2.9608 no . 4_655 H18 C1 3.3930 no . 4_655 H18 C9 3.4146 no . 4_655 H18 C10 3.2203 no . 1_656 H18 C10 3.0475 no . 4_655 H18 C11 3.5994 no . 1_656 H18 C17 3.5508 no . 4_555 H18 H10 2.4475 no . 1_656 H18 H10 2.6786 no . 4_655 H18 H22B 3.5887 no . 1_656 H19 N1 3.1938 no . 4_655 H19 C2 3.3687 no . 4_655 H19 C3 3.1002 no . 4_655 H19 C4 3.4337 no . 2_555 H19 C5 2.9892 no . 2_555 H19 H3 2.6202 no . 4_655 H19 H4 3.2534 no . 2_555 H19 H5 2.4148 no . 2_555 H21A S1 3.0220 no . 4_554 H21A O2 2.8883 no . 4_554 H21A C1 3.4041 no . 4_554 H21A C8 3.4893 no . 4_554 H21A C23 3.4028 no . 3_565 H21A H1 3.2913 no . 4_554 H21A H23A 2.8635 no . 3_565 H21A H23B 3.0734 no . 3_565 H21B S1 3.0438 no . 4_555 H21B N1 3.2098 no . 4_555 H21B C1 3.0962 no . 4_555 H21B C2 3.1556 no . 4_555 H21B C7 3.0357 no . 4_555 H21B H23A 3.0802 no . 3_565 H22A C2 3.0082 no . 4_555 H22A C3 2.9105 no . 4_555 H22A C4 3.5166 no . 2_454 H22A C4 3.1840 no . 4_555 H22A C5 3.5351 no . 4_555 H22A C7 3.3833 no . 4_555 H22A H3 3.2334 no . 4_555 H22A H4 2.5728 no . 2_454 H22A H17 3.5534 no . 4_454 H22B S1 3.0615 no . 4_554 H22B N1 3.1738 no . 4_554 H22B C1 3.1493 no . 4_554 H22B C2 2.9990 no . 4_554 H22B C6 3.5884 no . 4_554 H22B C7 2.8962 no . 4_554 H22B H4 2.8605 no . 2_454 H22B H18 3.5887 no . 1_454 H23A S1 3.2193 no . 4_554 H23A C6 3.5595 no . 4_554 H23A C7 3.4526 no . 4_554 H23A C21 3.4073 no . 3_565 H23A H6 3.3499 no . 4_554 H23A H12 3.2520 no . 3_565 H23A H21A 2.8635 no . 3_565 H23A H21B 3.0802 no . 3_565 H23A H23A 3.1056 no . 3_565 H23A H23B 3.4064 no . 3_565 H23B O2 3.3046 no . 2_555 H23B C5 3.1392 no . 4_555 H23B C6 2.8425 no . 4_555 H23B C7 3.2049 no . 4_555 H23B H1 3.1980 no . 2_555 H23B H5 3.4391 no . 4_555 H23B H6 2.9857 no . 4_555 H23B H21A 3.0734 no . 3_565 H23B H23A 3.4064 no . 3_565 H23C S2 3.2119 no . 3_565 H23C C6 3.4521 no . 4_554 H23C H3 3.4084 no . 2_454 H23C H4 3.2425 no . 2_454 H23C H6 3.4285 no . 4_554 H23C H12 3.5667 no . 3_565 H23C H16 3.5023 no . 2_555 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H1 N2 . . . 2.581(3) 0.827 1.82(4) 153(4) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 966983'