#------------------------------------------------------------------------------ #$Date: 2020-06-03 07:26:21 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252566 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240595.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_7240595 loop_ _publ_author_name 'Khan, Imran' 'Zhang, Haibo' 'Liu, Wei' 'Zhang, Liping' 'Peng, Fang' 'Chen, Yuchan' 'Zhang, Qingbo' 'Zhang, Guangtao' 'Zhang, Weimin' 'Zhang, Changsheng' _publ_section_title ; Identification and bioactivity evaluation of secondary metabolites from Antarctic-derived Penicillium chrysogenum CCTCC M 2020019 ; _journal_issue 35 _journal_name_full 'RSC Advances' _journal_page_first 20738 _journal_paper_doi 10.1039/D0RA03529G _journal_volume 10 _journal_year 2020 _chemical_compound_source 'Penicillium chrysogenum CCTCC M 2020019' _chemical_formula_moiety 'C2 H6 O S, C9 H6 N O' _chemical_formula_sum 'C11 H12 N O2 S' _chemical_formula_weight 222.28 _chemical_name_systematic 'Xanthocillin X' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-02-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-29 deposited with the CCDC. 2020-05-19 downloaded from the CCDC. ; _cell_angle_alpha 96.434(3) _cell_angle_beta 102.426(4) _cell_angle_gamma 94.819(3) _cell_formula_units_Z 2 _cell_length_a 6.4707(3) _cell_length_b 6.4978(2) _cell_length_c 13.6439(5) _cell_measurement_reflns_used 3518 _cell_measurement_temperature 100.0(5) _cell_measurement_theta_max 73.8230 _cell_measurement_theta_min 6.9200 _cell_volume 553.23(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(5) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.956 _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 -28.00 30.00 0.50 0.50 -- 0.00 -82.00 120.00 116 2 \w -19.00 8.00 0.50 0.50 -- 0.00 -82.00 -90.00 54 3 \w -46.00 -12.00 0.50 0.50 -- 0.00 -77.00-180.00 68 4 \w -45.00 7.00 0.50 0.50 -- 0.00 -77.00 30.00 104 5 \w -24.00 11.00 0.50 0.50 -- 0.00 -82.00-120.00 70 6 \w 55.00 122.00 0.50 0.50 -- 95.20 -77.00 -30.00 134 7 \w 6.00 109.00 0.50 0.50 -- 95.20 -15.00 90.00 206 8 \w 6.00 116.00 0.50 0.50 -- 95.20 -61.00-120.00 220 9 \w 24.00 123.00 0.50 0.50 -- 95.20 -82.00-120.00 198 10 \w 152.00 185.00 0.50 0.50 -- 95.20 30.00 60.00 66 11 \w 67.00 102.00 0.50 0.50 -- 95.20 -82.00 150.00 70 12 \w 22.00 82.00 0.50 0.50 -- 95.20 -82.00 30.00 120 13 \w 91.00 126.00 0.50 0.50 -- 95.20 -82.00 30.00 70 14 \w 44.00 71.00 0.50 0.50 -- 95.20 -82.00-180.00 54 15 \w 80.00 127.00 0.50 0.50 -- 95.20 77.00 60.00 94 16 \w 31.00 73.00 0.50 0.50 -- 95.20 -61.00 90.00 84 17 \w 80.00 138.00 0.50 0.50 -- 95.20 30.00 60.00 116 18 \w 6.00 112.00 0.50 0.50 -- 95.20 -82.00 90.00 212 19 \w 72.00 156.00 0.50 0.50 -- 95.20 15.00 0.00 168 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.2250881000 _diffrn_orient_matrix_UB_12 0.0838599000 _diffrn_orient_matrix_UB_13 -0.0075991000 _diffrn_orient_matrix_UB_21 0.0667553000 _diffrn_orient_matrix_UB_22 0.0494296000 _diffrn_orient_matrix_UB_23 0.1162551000 _diffrn_orient_matrix_UB_31 0.0711404000 _diffrn_orient_matrix_UB_32 -0.2194679000 _diffrn_orient_matrix_UB_33 0.0062108000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.956 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4537 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.956 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.078 _diffrn_reflns_theta_min 6.705 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.439 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65524 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear brownish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier brownish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.334 _exptl_crystal_description block _exptl_crystal_F_000 234 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.599 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.092 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2136 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.100 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0457 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1041P)^2^+0.0820P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1357 _refine_ls_wR_factor_ref 0.1367 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2030 _reflns_number_total 2136 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03529g2.cif _cod_data_source_block zhanghaibo_zys6-5_collect _cod_database_code 7240595 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula 'C22 H24 Cl2 N2 O4 ' _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. ; _reflns_odcompleteness_completeness 99.25 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C12(H12), C7(H7), C6(H6), C10(H10), C9(H9) 2.b Idealised Me refined as rotating group: C3(H3A,H3B,H3C), C4(H4A,H4B,H4C) 2.c Idealised tetrahedral OH refined as rotating group: O11(H11) ; _shelx_res_file ; TITL zhanghaibo_zys6-5_collect_a.res in P-1 zhanghaibo_zys6-5_collect.res created by SHELXL-2018/1 at 15:55:54 on 11-Feb-2020 REM Old TITL zhanghaibo_ZYS6-5_collect in P-1 REM SHELXT solution in P-1 REM R1 0.118, Rweak 0.007, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C11 N O2 Cl CELL 1.54184 6.4707 6.4978 13.6439 96.434 102.426 94.819 ZERR 2 0.0003 0.0002 0.0005 0.003 0.004 0.003 LATT 1 SFAC C H N O S UNIT 22 24 2 4 2 L.S. 4 PLAN 5 BOND $H LIST 6 MORE -1 CONF fmap 2 acta REM REM REM WGHT 0.104100 0.082000 FVAR 0.99311 S2 5 0.710521 0.600034 0.381377 11.00000 0.01918 0.01796 = 0.02233 0.00216 -0.00022 0.00012 O11 4 0.597333 0.025558 0.297059 11.00000 0.01592 0.01805 = 0.03038 0.00084 -0.00204 0.00239 AFIX 147 H11 2 0.632119 0.146385 0.324031 11.00000 -1.50000 AFIX 0 O1 4 0.738414 0.385770 0.413630 11.00000 0.02723 0.01660 = 0.02844 0.00341 -0.00171 -0.00123 N14 3 -0.374899 0.240665 0.079547 11.00000 0.01361 0.01541 = 0.02338 0.00275 0.00192 0.00252 C8 1 -0.026954 -0.046084 0.123052 11.00000 0.01512 0.01589 = 0.01970 0.00258 0.00384 0.00106 C12 1 -0.239371 -0.089103 0.057250 11.00000 0.01649 0.01500 = 0.01997 0.00101 0.00393 0.00081 AFIX 43 H12 2 -0.272349 -0.225199 0.024626 11.00000 -1.20000 AFIX 0 C7 1 0.103584 -0.209269 0.126485 11.00000 0.01856 0.01393 = 0.02069 0.00109 0.00419 0.00134 AFIX 43 H7 2 0.049362 -0.337782 0.088462 11.00000 -1.20000 AFIX 0 C13 1 -0.396642 0.033386 0.035255 11.00000 0.01647 0.01257 = 0.01949 0.00087 0.00521 -0.00001 C5 1 0.393876 0.006131 0.242057 11.00000 0.01489 0.01993 = 0.02012 0.00522 0.00323 0.00204 C6 1 0.309096 -0.184767 0.184356 11.00000 0.01780 0.01628 = 0.02337 0.00349 0.00376 0.00356 AFIX 43 H6 2 0.391094 -0.295696 0.184862 11.00000 -1.20000 AFIX 0 C10 1 0.267996 0.171058 0.240017 11.00000 0.01868 0.01506 = 0.02521 -0.00264 0.00178 0.00105 AFIX 43 H10 2 0.323207 0.299331 0.278053 11.00000 -1.20000 AFIX 0 C9 1 0.062009 0.144661 0.181825 11.00000 0.02002 0.01746 = 0.02652 0.00037 0.00274 0.00603 AFIX 43 H9 2 -0.019497 0.255940 0.181633 11.00000 -1.20000 AFIX 0 C3 1 0.957473 0.689500 0.353909 11.00000 0.02317 0.02218 = 0.02783 0.00317 0.00531 -0.00020 AFIX 137 H3A 2 1.071609 0.682988 0.411149 11.00000 -1.50000 H3B 2 0.954702 0.830824 0.339794 11.00000 -1.50000 H3C 2 0.979002 0.602832 0.296002 11.00000 -1.50000 AFIX 0 C4 1 0.734247 0.769225 0.496873 11.00000 0.03232 0.02653 = 0.02668 0.00041 0.00820 0.00506 AFIX 137 H4A 2 0.612509 0.738322 0.524533 11.00000 -1.50000 H4B 2 0.741759 0.911405 0.483701 11.00000 -1.50000 H4C 2 0.861215 0.748822 0.544420 11.00000 -1.50000 AFIX 0 C15 1 -0.366218 0.412090 0.116248 11.00000 0.02084 0.01905 = 0.03446 0.00048 0.00092 0.00445 HKLF 4 REM zhanghaibo_zys6-5_collect_a.res in P-1 REM R1 = 0.0457 for 2030 Fo > 4sig(Fo) and 0.0465 for all 2136 data REM 139 parameters refined using 0 restraints END WGHT 0.1041 0.0820 REM Highest difference peak 0.599, deepest hole -0.633, 1-sigma level 0.092 Q1 1 0.6079 0.6159 0.3190 11.00000 0.05 0.60 Q2 1 -0.1421 -0.0597 0.0821 11.00000 0.05 0.33 Q3 1 0.7099 0.6236 0.4602 11.00000 0.05 0.32 Q4 1 0.8178 0.3664 0.4782 11.00000 0.05 0.31 Q5 1 0.5351 0.6513 0.4026 11.00000 0.05 0.29 ; _shelx_res_checksum 39387 _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 2.008 _oxdiff_exptl_absorpt_empirical_full_min 0.581 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S2 S 0.71052(5) 0.60003(5) 0.38138(3) 0.0207(2) Uani 1 1 d . . . . . O11 O 0.59733(17) 0.02556(18) 0.29706(9) 0.0227(3) Uani 1 1 d . . . . . H11 H 0.632119 0.146385 0.324031 0.034 Uiso 1 1 calc GR . . . . O1 O 0.73841(19) 0.38577(17) 0.41363(9) 0.0255(3) Uani 1 1 d . . . . . N14 N -0.37490(19) 0.2407(2) 0.07955(10) 0.0178(3) Uani 1 1 d . . . . . C8 C -0.0270(2) -0.0461(2) 0.12305(11) 0.0169(3) Uani 1 1 d . . . . . C12 C -0.2394(2) -0.0891(2) 0.05725(11) 0.0173(3) Uani 1 1 d . . . . . H12 H -0.272349 -0.225199 0.024626 0.021 Uiso 1 1 calc R . . . . C7 C 0.1036(2) -0.2093(2) 0.12649(12) 0.0179(3) Uani 1 1 d . . . . . H7 H 0.049362 -0.337782 0.088462 0.021 Uiso 1 1 calc R . . . . C13 C -0.3966(2) 0.0334(2) 0.03525(11) 0.0162(3) Uani 1 1 d . . . . . C5 C 0.3939(2) 0.0061(2) 0.24206(12) 0.0182(3) Uani 1 1 d . . . . . C6 C 0.3091(2) -0.1848(2) 0.18436(12) 0.0191(3) Uani 1 1 d . . . . . H6 H 0.391094 -0.295696 0.184862 0.023 Uiso 1 1 calc R . . . . C10 C 0.2680(2) 0.1711(2) 0.24002(12) 0.0206(4) Uani 1 1 d . . . . . H10 H 0.323207 0.299331 0.278053 0.025 Uiso 1 1 calc R . . . . C9 C 0.0620(3) 0.1447(3) 0.18183(12) 0.0217(4) Uani 1 1 d . . . . . H9 H -0.019497 0.255940 0.181633 0.026 Uiso 1 1 calc R . . . . C3 C 0.9575(3) 0.6895(3) 0.35391(13) 0.0246(4) Uani 1 1 d . . . . . H3A H 1.071609 0.682988 0.411149 0.037 Uiso 1 1 calc GR . . . . H3B H 0.954702 0.830824 0.339794 0.037 Uiso 1 1 calc GR . . . . H3C H 0.979002 0.602832 0.296002 0.037 Uiso 1 1 calc GR . . . . C4 C 0.7342(3) 0.7692(3) 0.49687(13) 0.0284(4) Uani 1 1 d . . . . . H4A H 0.612509 0.738322 0.524533 0.043 Uiso 1 1 calc GR . . . . H4B H 0.741759 0.911405 0.483701 0.043 Uiso 1 1 calc GR . . . . H4C H 0.861215 0.748822 0.544420 0.043 Uiso 1 1 calc GR . . . . C15 C -0.3662(3) 0.4121(3) 0.11625(14) 0.0257(4) Uani 1 1 d . . . . . 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 S2 0.0192(3) 0.0180(3) 0.0223(3) 0.00216(18) -0.00022(18) 0.00012(18) O11 0.0159(6) 0.0180(6) 0.0304(6) 0.0008(5) -0.0020(5) 0.0024(4) O1 0.0272(6) 0.0166(6) 0.0284(6) 0.0034(5) -0.0017(5) -0.0012(5) N14 0.0136(6) 0.0154(7) 0.0234(7) 0.0027(5) 0.0019(5) 0.0025(5) C8 0.0151(7) 0.0159(8) 0.0197(7) 0.0026(6) 0.0038(6) 0.0011(6) C12 0.0165(7) 0.0150(7) 0.0200(7) 0.0010(6) 0.0039(6) 0.0008(6) C7 0.0186(8) 0.0139(7) 0.0207(7) 0.0011(6) 0.0042(6) 0.0013(6) C13 0.0165(8) 0.0126(7) 0.0195(7) 0.0009(6) 0.0052(6) 0.0000(6) C5 0.0149(7) 0.0199(8) 0.0201(7) 0.0052(6) 0.0032(6) 0.0020(6) C6 0.0178(7) 0.0163(8) 0.0234(8) 0.0035(6) 0.0038(6) 0.0036(6) C10 0.0187(8) 0.0151(8) 0.0252(8) -0.0026(6) 0.0018(6) 0.0011(6) C9 0.0200(8) 0.0175(8) 0.0265(8) 0.0004(6) 0.0027(6) 0.0060(6) C3 0.0232(8) 0.0222(9) 0.0278(9) 0.0032(6) 0.0053(6) -0.0002(6) C4 0.0323(9) 0.0265(9) 0.0267(9) 0.0004(7) 0.0082(7) 0.0051(7) C15 0.0208(8) 0.0190(9) 0.0345(9) 0.0005(7) 0.0009(7) 0.0044(6) 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 O1 S2 C3 105.66(7) . . ? O1 S2 C4 104.76(8) . . ? C3 S2 C4 98.06(9) . . ? C5 O11 H11 109.5 . . ? C15 N14 C13 177.03(15) . . ? C7 C8 C12 117.18(13) . . ? C9 C8 C12 126.05(14) . . ? C9 C8 C7 116.75(14) . . ? C8 C12 H12 114.3 . . ? C13 C12 C8 131.42(14) . . ? C13 C12 H12 114.3 . . ? C8 C7 H7 118.9 . . ? C6 C7 C8 122.18(14) . . ? C6 C7 H7 118.9 . . ? N14 C13 C13 113.57(15) . 2_455 ? C12 C13 N14 121.60(13) . . ? C12 C13 C13 124.83(17) . 2_455 ? O11 C5 C6 118.45(13) . . ? O11 C5 C10 122.48(14) . . ? C6 C5 C10 119.07(14) . . ? C7 C6 C5 120.00(14) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C5 C10 H10 119.8 . . ? C9 C10 C5 120.44(15) . . ? C9 C10 H10 119.8 . . ? C8 C9 H9 119.2 . . ? C10 C9 C8 121.55(14) . . ? C10 C9 H9 119.2 . . ? S2 C3 H3A 109.5 . . ? S2 C3 H3B 109.5 . . ? S2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? S2 C4 H4A 109.5 . . ? S2 C4 H4B 109.5 . . ? S2 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 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 S2 O1 1.5198(11) . ? S2 C3 1.7839(17) . ? S2 C4 1.7874(18) . ? O11 H11 0.8200 . ? O11 C5 1.3557(19) . ? N14 C13 1.3958(19) . ? N14 C15 1.161(2) . ? C8 C12 1.457(2) . ? C8 C7 1.409(2) . ? C8 C9 1.403(2) . ? C12 H12 0.9300 . ? C12 C13 1.348(2) . ? C7 H7 0.9300 . ? C7 C6 1.379(2) . ? C13 C13 1.469(3) 2_455 ? C5 C6 1.393(2) . ? C5 C10 1.399(2) . ? C6 H6 0.9300 . ? C10 H10 0.9300 . ? C10 C9 1.383(2) . ? C9 H9 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 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 O11 C5 C6 C7 -179.18(14) . . . . ? O11 C5 C10 C9 179.23(14) . . . . ? C8 C12 C13 N14 -1.4(3) . . . . ? C8 C12 C13 C13 178.73(16) . . . 2_455 ? C8 C7 C6 C5 0.1(2) . . . . ? C12 C8 C7 C6 178.53(14) . . . . ? C12 C8 C9 C10 -178.30(15) . . . . ? C7 C8 C12 C13 -177.65(15) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C5 C10 C9 C8 -0.3(3) . . . . ? C6 C5 C10 C9 0.2(2) . . . . ? C10 C5 C6 C7 -0.2(2) . . . . ? C9 C8 C12 C13 0.8(3) . . . . ? C9 C8 C7 C6 -0.1(2) . . . . ?