#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:42:06 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270505 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158297.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_7158297 loop_ _publ_author_name 'Bandyopadhyay, Debashruti' 'Thirupathi, Annaram' 'Radhakrishnan, Divya' 'Panigrahi, Adyasha' 'Peruncheralathan, S.' _publ_section_title ; Triflic acid-mediated N-heteroannulation of \b-anilino-\b-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines. ; _journal_issue 39 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8544 _journal_page_last 8553 _journal_paper_doi 10.1039/d1ob01151k _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C15 H18 N2 O2 S' _chemical_formula_sum 'C15 H18 N2 O2 S' _chemical_formula_weight 290.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2021-06-12 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _audit_update_record ; 2021-06-14 deposited with the CCDC. 2021-09-06 downloaded from the CCDC. ; _cell_angle_alpha 90.0000(9) _cell_angle_beta 93.9407(9) _cell_angle_gamma 90.0000(10) _cell_formula_units_Z 4 _cell_length_a 9.31410(10) _cell_length_b 7.60332(10) _cell_length_c 20.7811(2) _cell_measurement_reflns_used 8739 _cell_measurement_temperature 297.4(3) _cell_measurement_theta_max 74.8940 _cell_measurement_theta_min 4.7700 _cell_volume 1468.20(3) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'SIR2004 (Burla et al., 2007)' _diffrn_ambient_environment air _diffrn_ambient_temperature 297.4(3) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 200K' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -105.00 -35.00 0.50 0.83 -- -38.50 -36.00-168.00 140 2 \w -42.00 28.00 0.50 0.83 -- -38.50 36.00 -12.00 140 3 \w 46.00 116.00 0.50 0.83 -- 49.56 36.00 -12.00 140 4 \w -17.00 53.00 0.50 0.83 -- 49.56 -36.00-168.00 140 5 \w 36.00 106.00 0.50 3.29 -- 102.63 -36.00-168.00 140 6 \w 100.00 169.00 0.50 3.29 -- 102.63 36.00 -12.00 138 7 \w -86.00 -6.00 0.50 0.83 -- -38.50 125.00 60.00 160 8 \w 46.00 116.00 0.50 0.83 -- 49.56 38.00 150.00 140 9 \w 103.00 167.00 0.50 3.29 -- 102.63 77.00 -90.00 128 10 \w 97.00 168.00 0.50 3.29 -- 102.63 125.00-120.00 142 11 \w 103.00 167.00 0.50 3.29 -- 102.63 77.00 120.00 128 12 \w 98.00 167.00 0.50 3.29 -- 102.63 45.00 60.00 138 13 \w 34.00 107.00 0.50 3.29 -- 102.63 -94.00 30.00 146 14 \w 34.00 107.00 0.50 3.29 -- 102.63 -94.00 150.00 146 15 \w 38.00 107.00 0.50 3.29 -- 102.63 -45.00 -90.00 138 16 \w 98.00 167.00 0.50 3.29 -- 102.63 45.00 150.00 138 17 \w 98.00 167.00 0.50 3.29 -- 102.63 45.00-150.00 138 18 \w 43.00 70.00 0.50 3.29 -- 102.63 -94.00 0.00 54 19 \w 64.00 105.00 0.50 3.29 -- 102.63 -45.00 0.00 82 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Pilatus 200K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1630217000 _diffrn_orient_matrix_UB_12 0.0358459000 _diffrn_orient_matrix_UB_13 0.0018058000 _diffrn_orient_matrix_UB_21 -0.0228741000 _diffrn_orient_matrix_UB_22 0.1781107000 _diffrn_orient_matrix_UB_23 0.0331185000 _diffrn_orient_matrix_UB_31 0.0196981000 _diffrn_orient_matrix_UB_32 -0.0896956000 _diffrn_orient_matrix_UB_33 0.0664954000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11800 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.421 _diffrn_reflns_theta_min 4.265 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.985 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.314 _exptl_crystal_description needle _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.362 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2960 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.4866P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1172 _refine_ls_wR_factor_ref 0.1186 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2769 _reflns_number_total 2960 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01151k2.cif _cod_data_source_block peru-db-978 _cod_depositor_comments 'Adding full bibliography for 7158297.cif.' _cod_database_code 7158297 _chemical_oxdiff_formula 'C60 H72 N8 O8 S4 ' _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 0.692 _shelx_estimated_absorpt_t_min 0.587 _diffrn_oxdiff_digest_frames ; 01d1cbffb85421faf64b7e7f0ab1b8c28900038a7b5 ; _diffrn_oxdiff_digest_hkl ; 0153dc9a41d032b6b662c2e5fe68df313125c4 ; _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C15(H15A,H15B) 2.b Aromatic/amide H refined with riding coordinates: C7(H7), C9(H9) 2.c X=CH2 refined with riding coordinates: N18(H18A,H18B) 2.d Idealised Me refined as rotating group: C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C12(H12A,H12B,H12C), C16(H16A,H16B, H16C) ; _shelx_res_file ; peru-db-978.res created by SHELXL-2014/7 TITL PERU-DB-978 in P21/c #14 REM reset to P21/c #14 CELL 1.54184 9.314102 7.60332 20.781141 90 93.9407 90 ZERR 4 0.000103 0.0001 0.000212 0.0009 0.0009 0.001 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 60 72 8 8 4 L.S. 4 PLAN 2 SIZE 0.2 0.3 0.25 CONF BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.062377 0.486640 EXTI 0.001335 FVAR 5.32069 S11 5 0.326574 0.010194 0.259805 11.00000 0.05065 0.06740 = 0.04178 0.00753 0.00055 0.00606 C5 1 0.390095 -0.185188 0.468132 11.00000 0.04107 0.03730 = 0.03947 -0.00417 0.00167 -0.00289 C10 1 0.496419 -0.181544 0.422615 11.00000 0.04020 0.03902 = 0.04006 -0.00371 0.00039 -0.00138 N1 3 0.472505 -0.121102 0.360493 11.00000 0.03950 0.04810 = 0.03974 -0.00094 0.00215 0.00169 C4 1 0.248397 -0.126980 0.444834 11.00000 0.04030 0.04251 = 0.04459 -0.00654 0.00426 -0.00227 C2 1 0.343080 -0.072035 0.340228 11.00000 0.04273 0.04173 = 0.03832 -0.00496 0.00070 -0.00022 C3 1 0.222466 -0.077302 0.379436 11.00000 0.03788 0.04442 = 0.04225 -0.00693 0.00005 -0.00044 N18 3 0.140133 -0.124508 0.484073 11.00000 0.04422 0.09065 = 0.05100 0.00620 0.01135 0.00729 AFIX 93 H18A 2 0.055418 -0.092848 0.469482 11.00000 -1.20000 H18B 2 0.155356 -0.154581 0.523851 11.00000 -1.20000 AFIX 0 C7 1 0.570334 -0.303475 0.545311 11.00000 0.05835 0.04723 = 0.04228 0.00308 -0.00750 -0.00228 AFIX 43 H7 2 0.596357 -0.344233 0.586671 11.00000 -1.20000 AFIX 0 C9 1 0.637288 -0.241370 0.439536 11.00000 0.04006 0.04874 = 0.04935 -0.00147 0.00163 0.00026 AFIX 43 H9 2 0.705586 -0.239063 0.408938 11.00000 -1.20000 AFIX 0 O14 4 0.053883 -0.035828 0.291685 11.00000 0.04436 0.08580 = 0.05155 -0.00480 -0.00894 0.00701 C8 1 0.675042 -0.302628 0.500111 11.00000 0.04686 0.04433 = 0.05326 -0.00091 -0.00864 -0.00094 C6 1 0.431321 -0.247455 0.531960 11.00000 0.05301 0.04307 = 0.04084 -0.00249 0.00169 -0.00453 O17 4 -0.023994 0.001468 0.388280 11.00000 0.04573 0.15089 = 0.06245 -0.00852 0.00195 0.02848 C13 1 0.074845 -0.032302 0.355167 11.00000 0.04144 0.05887 = 0.05060 -0.00581 -0.00120 0.00129 C19 1 0.334713 -0.258389 0.587150 11.00000 0.06788 0.07801 = 0.04625 0.00795 0.00604 0.00276 AFIX 137 H19A 2 0.300011 -0.143039 0.596670 11.00000 -1.50000 H19B 2 0.387965 -0.305024 0.624510 11.00000 -1.50000 H19C 2 0.254658 -0.334065 0.575405 11.00000 -1.50000 AFIX 0 C20 1 0.825640 -0.367324 0.518420 11.00000 0.05248 0.06895 = 0.07262 0.00646 -0.01163 0.00478 AFIX 137 H20A 2 0.871316 -0.289972 0.550092 11.00000 -1.50000 H20B 2 0.880069 -0.369278 0.480838 11.00000 -1.50000 H20C 2 0.821264 -0.483846 0.535968 11.00000 -1.50000 AFIX 0 C15 1 -0.089242 0.007010 0.263659 11.00000 0.04926 0.09240 = 0.07488 0.00112 -0.01999 0.00727 AFIX 23 H15A 2 -0.114709 0.126233 0.274970 11.00000 -1.20000 H15B 2 -0.159719 -0.072635 0.279833 11.00000 -1.20000 AFIX 0 C12 1 0.512268 0.018485 0.241695 11.00000 0.05780 0.06670 = 0.05097 0.01239 0.00993 -0.00191 AFIX 137 H12A 2 0.519574 0.069807 0.199839 11.00000 -1.50000 H12B 2 0.551070 -0.098509 0.242041 11.00000 -1.50000 H12C 2 0.565403 0.088588 0.273526 11.00000 -1.50000 AFIX 0 C16 1 -0.087093 -0.010146 0.193730 11.00000 0.09831 0.10133 = 0.07458 -0.00606 -0.03535 0.02475 AFIX 137 H16A 2 -0.177558 0.028422 0.173661 11.00000 -1.50000 H16B 2 -0.071363 -0.130982 0.182814 11.00000 -1.50000 H16C 2 -0.010946 0.060844 0.178752 11.00000 -1.50000 AFIX 0 HKLF 4 REM PERU-DB-978 in P21/c #14 REM R1 = 0.0414 for 2769 Fo > 4sig(Fo) and 0.0434 for all 2960 data REM 186 parameters refined using 0 restraints END WGHT 0.0646 0.4094 REM Highest difference peak 0.362, deepest hole -0.191, 1-sigma level 0.040 Q1 1 0.7419 -0.2563 0.3904 11.00000 0.05 0.36 Q2 1 0.5725 -0.3545 0.6127 11.00000 0.05 0.35 ; _shelx_res_checksum 26145 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.281 _oxdiff_exptl_absorpt_empirical_full_min 0.676 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 S11 S 0.32657(5) 0.01019(6) 0.25980(2) 0.05340(17) Uani 1 1 d . . . . . C5 C 0.39010(16) -0.18519(19) 0.46813(7) 0.0393(3) Uani 1 1 d . . . . . C10 C 0.49642(15) -0.1815(2) 0.42261(7) 0.0399(3) Uani 1 1 d . . . . . N1 N 0.47250(13) -0.12110(18) 0.36049(6) 0.0425(3) Uani 1 1 d . . . . . C4 C 0.24840(16) -0.1270(2) 0.44483(8) 0.0424(3) Uani 1 1 d . . . . . C2 C 0.34308(16) -0.0720(2) 0.34023(7) 0.0410(3) Uani 1 1 d . . . . . C3 C 0.22247(16) -0.0773(2) 0.37944(7) 0.0416(3) Uani 1 1 d . . . . . N18 N 0.14013(16) -0.1245(2) 0.48407(7) 0.0616(4) Uani 1 1 d . . . . . H18A H 0.0554 -0.0928 0.4695 0.074 Uiso 1 1 calc R . . . . H18B H 0.1554 -0.1546 0.5239 0.074 Uiso 1 1 calc R . . . . C7 C 0.57033(19) -0.3035(2) 0.54531(8) 0.0498(4) Uani 1 1 d . . . . . H7 H 0.5964 -0.3442 0.5867 0.060 Uiso 1 1 calc R . . . . C9 C 0.63729(17) -0.2414(2) 0.43954(8) 0.0461(4) Uani 1 1 d . . . . . H9 H 0.7056 -0.2391 0.4089 0.055 Uiso 1 1 calc R . . . . O14 O 0.05388(13) -0.0358(2) 0.29168(6) 0.0611(4) Uani 1 1 d . . . . . C8 C 0.67504(18) -0.3026(2) 0.50011(8) 0.0487(4) Uani 1 1 d . . . . . C6 C 0.43132(18) -0.2475(2) 0.53196(8) 0.0457(4) Uani 1 1 d . . . . . O17 O -0.02399(15) 0.0015(3) 0.38828(8) 0.0864(6) Uani 1 1 d . . . . . C13 C 0.07485(18) -0.0323(2) 0.35517(9) 0.0505(4) Uani 1 1 d . . . . . C19 C 0.3347(2) -0.2584(3) 0.58715(9) 0.0639(5) Uani 1 1 d . . . . . H19A H 0.3000 -0.1430 0.5967 0.096 Uiso 1 1 calc GR . . . . H19B H 0.3880 -0.3050 0.6245 0.096 Uiso 1 1 calc GR . . . . H19C H 0.2547 -0.3341 0.5754 0.096 Uiso 1 1 calc GR . . . . C20 C 0.8256(2) -0.3673(3) 0.51842(11) 0.0654(5) Uani 1 1 d . . . . . H20A H 0.8713 -0.2900 0.5501 0.098 Uiso 1 1 calc GR . . . . H20B H 0.8801 -0.3693 0.4808 0.098 Uiso 1 1 calc GR . . . . H20C H 0.8213 -0.4838 0.5360 0.098 Uiso 1 1 calc GR . . . . C15 C -0.0892(2) 0.0070(3) 0.26366(12) 0.0733(6) Uani 1 1 d . . . . . H15A H -0.1147 0.1262 0.2750 0.088 Uiso 1 1 calc R . . . . H15B H -0.1597 -0.0726 0.2798 0.088 Uiso 1 1 calc R . . . . C12 C 0.5123(2) 0.0185(3) 0.24169(10) 0.0582(5) Uani 1 1 d . . . . . H12A H 0.5196 0.0698 0.1998 0.087 Uiso 1 1 calc GR . . . . H12B H 0.5511 -0.0985 0.2420 0.087 Uiso 1 1 calc GR . . . . H12C H 0.5654 0.0886 0.2735 0.087 Uiso 1 1 calc GR . . . . C16 C -0.0871(3) -0.0101(4) 0.19373(13) 0.0933(9) Uani 1 1 d . . . . . H16A H -0.1776 0.0284 0.1737 0.140 Uiso 1 1 calc GR . . . . H16B H -0.0714 -0.1310 0.1828 0.140 Uiso 1 1 calc GR . . . . H16C H -0.0109 0.0608 0.1788 0.140 Uiso 1 1 calc GR . . . . 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 S11 0.0506(3) 0.0674(3) 0.0418(3) 0.00753(18) 0.00055(18) 0.00606(18) C5 0.0411(7) 0.0373(7) 0.0395(7) -0.0042(6) 0.0017(6) -0.0029(6) C10 0.0402(7) 0.0390(7) 0.0401(8) -0.0037(6) 0.0004(6) -0.0014(6) N1 0.0395(6) 0.0481(7) 0.0397(6) -0.0009(5) 0.0022(5) 0.0017(5) C4 0.0403(7) 0.0425(8) 0.0446(8) -0.0065(6) 0.0043(6) -0.0023(6) C2 0.0427(8) 0.0417(8) 0.0383(8) -0.0050(6) 0.0007(6) -0.0002(6) C3 0.0379(7) 0.0444(8) 0.0422(8) -0.0069(6) 0.0001(6) -0.0004(6) N18 0.0442(7) 0.0907(12) 0.0510(8) 0.0062(8) 0.0113(6) 0.0073(8) C7 0.0583(9) 0.0472(9) 0.0423(8) 0.0031(7) -0.0075(7) -0.0023(7) C9 0.0401(8) 0.0487(9) 0.0493(9) -0.0015(7) 0.0016(6) 0.0003(6) O14 0.0444(6) 0.0858(9) 0.0516(7) -0.0048(6) -0.0089(5) 0.0070(6) C8 0.0469(8) 0.0443(8) 0.0533(9) -0.0009(7) -0.0086(7) -0.0009(7) C6 0.0530(9) 0.0431(8) 0.0408(8) -0.0025(6) 0.0017(6) -0.0045(7) O17 0.0457(7) 0.1509(17) 0.0624(9) -0.0085(9) 0.0020(6) 0.0285(8) C13 0.0414(8) 0.0589(10) 0.0506(9) -0.0058(8) -0.0012(7) 0.0013(7) C19 0.0679(12) 0.0780(13) 0.0462(10) 0.0079(9) 0.0060(8) 0.0028(10) C20 0.0525(10) 0.0690(12) 0.0726(13) 0.0065(10) -0.0116(9) 0.0048(9) C15 0.0493(10) 0.0924(16) 0.0749(14) 0.0011(11) -0.0200(10) 0.0073(10) C12 0.0578(10) 0.0667(12) 0.0510(10) 0.0124(8) 0.0099(8) -0.0019(8) C16 0.0983(19) 0.101(2) 0.0746(16) -0.0061(13) -0.0353(14) 0.0247(14) 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 S11 C12 100.76(8) . . ? C10 C5 C4 115.80(14) . . ? C10 C5 C6 117.95(14) . . ? C6 C5 C4 126.25(14) . . ? N1 C10 C5 123.95(13) . . ? N1 C10 C9 115.48(14) . . ? C9 C10 C5 120.57(14) . . ? C2 N1 C10 119.06(13) . . ? C3 C4 C5 119.71(13) . . ? N18 C4 C5 120.60(15) . . ? N18 C4 C3 119.66(14) . . ? N1 C2 S11 114.95(11) . . ? N1 C2 C3 123.50(14) . . ? C3 C2 S11 121.52(11) . . ? C4 C3 C2 117.70(13) . . ? C4 C3 C13 119.00(14) . . ? C2 C3 C13 123.30(14) . . ? C4 N18 H18A 120.0 . . ? C4 N18 H18B 120.0 . . ? H18A N18 H18B 120.0 . . ? C8 C7 H7 118.2 . . ? C6 C7 H7 118.2 . . ? C6 C7 C8 123.63(15) . . ? C10 C9 H9 119.5 . . ? C8 C9 C10 121.08(15) . . ? C8 C9 H9 119.5 . . ? C13 O14 C15 117.64(16) . . ? C7 C8 C20 120.48(16) . . ? C9 C8 C7 118.23(15) . . ? C9 C8 C20 121.28(17) . . ? C5 C6 C19 125.82(15) . . ? C7 C6 C5 118.53(15) . . ? C7 C6 C19 115.65(15) . . ? O14 C13 C3 114.08(15) . . ? O17 C13 C3 125.58(17) . . ? O17 C13 O14 120.31(16) . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C8 C20 H20A 109.5 . . ? C8 C20 H20B 109.5 . . ? C8 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O14 C15 H15A 110.2 . . ? O14 C15 H15B 110.2 . . ? O14 C15 C16 107.7(2) . . ? H15A C15 H15B 108.5 . . ? C16 C15 H15A 110.2 . . ? C16 C15 H15B 110.2 . . ? S11 C12 H12A 109.5 . . ? S11 C12 H12B 109.5 . . ? S11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 S11 C2 1.7811(16) . ? S11 C12 1.796(2) . ? C5 C10 1.416(2) . ? C5 C4 1.444(2) . ? C5 C6 1.436(2) . ? C10 N1 1.374(2) . ? C10 C9 1.410(2) . ? N1 C2 1.3038(19) . ? C4 C3 1.415(2) . ? C4 N18 1.340(2) . ? C2 C3 1.433(2) . ? C3 C13 1.472(2) . ? N18 H18A 0.8600 . ? N18 H18B 0.8600 . ? C7 H7 0.9300 . ? C7 C8 1.400(2) . ? C7 C6 1.373(2) . ? C9 H9 0.9300 . ? C9 C8 1.365(2) . ? O14 C13 1.321(2) . ? O14 C15 1.455(2) . ? C8 C20 1.510(2) . ? C6 C19 1.508(2) . ? O17 C13 1.214(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.461(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 S11 C2 C3 C4 -173.42(12) . . . . ? S11 C2 C3 C13 6.0(2) . . . . ? C5 C10 N1 C2 -3.7(2) . . . . ? C5 C10 C9 C8 -0.6(2) . . . . ? C5 C4 C3 C2 -5.6(2) . . . . ? C5 C4 C3 C13 175.01(14) . . . . ? C10 C5 C4 C3 2.3(2) . . . . ? C10 C5 C4 N18 -179.70(15) . . . . ? C10 C5 C6 C7 -1.3(2) . . . . ? C10 C5 C6 C19 178.94(16) . . . . ? C10 N1 C2 S11 178.12(11) . . . . ? C10 N1 C2 C3 0.0(2) . . . . ? C10 C9 C8 C7 -0.4(2) . . . . ? C10 C9 C8 C20 179.83(16) . . . . ? N1 C10 C9 C8 179.20(15) . . . . ? N1 C2 C3 C4 4.5(2) . . . . ? N1 C2 C3 C13 -176.04(15) . . . . ? C4 C5 C10 N1 2.5(2) . . . . ? C4 C5 C10 C9 -177.77(14) . . . . ? C4 C5 C6 C7 177.82(15) . . . . ? C4 C5 C6 C19 -1.9(3) . . . . ? C4 C3 C13 O14 -162.10(15) . . . . ? C4 C3 C13 O17 16.0(3) . . . . ? C2 C3 C13 O14 18.5(2) . . . . ? C2 C3 C13 O17 -163.44(19) . . . . ? N18 C4 C3 C2 176.42(15) . . . . ? N18 C4 C3 C13 -3.0(2) . . . . ? C9 C10 N1 C2 176.51(14) . . . . ? C8 C7 C6 C5 0.3(3) . . . . ? C8 C7 C6 C19 -179.90(17) . . . . ? C6 C5 C10 N1 -178.32(14) . . . . ? C6 C5 C10 C9 1.4(2) . . . . ? C6 C5 C4 C3 -176.84(15) . . . . ? C6 C5 C4 N18 1.2(2) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C6 C7 C8 C20 -179.69(17) . . . . ? C13 O14 C15 C16 -178.5(2) . . . . ? C15 O14 C13 C3 179.98(17) . . . . ? C15 O14 C13 O17 1.8(3) . . . . ? C12 S11 C2 N1 -7.46(15) . . . . ? C12 S11 C2 C3 170.65(14) . . . . ?