#------------------------------------------------------------------------------ #$Date: 2024-02-04 13:39:27 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289450 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247791.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_7247791 loop_ _publ_author_name 'Liu, Yumin' 'Gong, Junbo' 'Yan, Dongpeng' 'Wang, Jingkang' _publ_section_title ; Insight into polymorphism in weakly polar systems using favorable connection motifs ; _journal_issue 2 _journal_name_full CrystEngComm _journal_page_first 153 _journal_page_last 159 _journal_paper_doi 10.1039/D3CE00856H _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C15 H12 O2' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 _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 dual _audit_creation_date 2020-07-26 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-07-31 deposited with the CCDC. 2023-11-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.444(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5547(8) _cell_length_b 11.7675(6) _cell_length_c 7.7848(6) _cell_measurement_reflns_used 5397 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 32.6770 _cell_measurement_theta_min 3.1550 _cell_volume 1118.59(13) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection CrystalClear(Rigaku,2008) _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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_temperature 113.15 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 -115.00 65.00 1.00 3.00 -- -25.00 45.00 0.00 180 2 \w -115.00 65.00 1.00 3.00 -- -25.00 45.00 90.00 180 3 \w -115.00 65.00 1.00 3.00 -- -25.00 45.00 180.00 180 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0519552000 _diffrn_orient_matrix_UB_12 0.0211416000 _diffrn_orient_matrix_UB_13 -0.0448905000 _diffrn_orient_matrix_UB_21 0.0018739000 _diffrn_orient_matrix_UB_22 0.0404928000 _diffrn_orient_matrix_UB_23 0.0681667000 _diffrn_orient_matrix_UB_31 0.0259505000 _diffrn_orient_matrix_UB_32 0.0393301000 _diffrn_orient_matrix_UB_33 -0.0459434000 _diffrn_radiation_monochromator confocal _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 11617 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 3.199 _diffrn_source 'rotating anode' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.66598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.274 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2276 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0474 _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^)+(0.0543P)^2^+0.4038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1138 _refine_ls_wR_factor_ref 0.1232 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1836 _reflns_number_total 2276 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00856h2.cif _cod_data_source_block r20200716a _cod_depositor_comments 'Adding full bibliography for 7247790--7247791.cif.' _cod_database_code 7247791 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C11 H10 N O' _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 0.986 _shelx_estimated_absorpt_t_min 0.983 _reflns_odcompleteness_completeness 99.46 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15) 2.b Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL r20200716a_a.res in P2(1)/c r20200716a.res created by SHELXL-2018/3 at 19:46:49 on 26-Jul-2020 REM Old TITL r20200716a in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.151, Rweak 0.345, Alpha 0.028 REM 0.727 for 125 systematic absences, Orientation as input REM Formula found by SHELXT: C15 O2 CELL 0.71073 12.5547 11.7675 7.7848 90 103.444 90 ZERR 4 0.0008 0.0006 0.0006 0 0.007 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 60 48 8 L.S. 4 0 0 PLAN 20 SIZE 0.2 0.18 0.16 TEMP -160 list 4 CONF HTAB BOND $H fmap 2 53 acta OMIT 1 0 0 OMIT 0 2 1 REM REM REM WGHT 0.054300 0.403800 FVAR 1.61003 O1 3 0.585701 0.904197 0.359669 11.00000 0.03397 0.01785 = 0.05654 -0.00199 0.01892 -0.00139 AFIX 147 H1 2 0.645984 0.917282 0.334198 11.00000 -1.50000 AFIX 0 O2 3 0.761456 0.869709 0.282659 11.00000 0.03402 0.01796 = 0.04732 0.00195 0.01440 -0.00250 C1 1 0.393845 0.840778 0.437600 11.00000 0.02999 0.02455 = 0.03298 -0.00359 0.00665 0.00189 AFIX 43 H1A 2 0.412979 0.918880 0.437482 11.00000 -1.20000 AFIX 0 C2 1 0.295314 0.809275 0.475206 11.00000 0.02876 0.03487 = 0.03728 -0.00473 0.01017 0.00592 AFIX 43 H2 2 0.247412 0.865716 0.501605 11.00000 -1.20000 AFIX 0 C3 1 0.266685 0.695714 0.474325 11.00000 0.02680 0.03988 = 0.03217 -0.00159 0.00942 -0.00269 AFIX 43 H3 2 0.199030 0.674154 0.499638 11.00000 -1.20000 AFIX 0 C4 1 0.336660 0.613670 0.436561 11.00000 0.03482 0.02673 = 0.03592 -0.00190 0.01094 -0.00482 AFIX 43 H4 2 0.317018 0.535684 0.436001 11.00000 -1.20000 AFIX 0 C5 1 0.435158 0.644777 0.399600 11.00000 0.03022 0.02259 = 0.03484 -0.00084 0.01046 0.00019 AFIX 43 H5 2 0.482889 0.587979 0.373727 11.00000 -1.20000 AFIX 0 C6 1 0.464838 0.758694 0.400045 11.00000 0.02501 0.02337 = 0.02272 -0.00175 0.00417 0.00135 C7 1 0.569260 0.795476 0.359710 11.00000 0.02905 0.01919 = 0.02406 -0.00006 0.00422 -0.00151 C8 1 0.647359 0.720631 0.324388 11.00000 0.02618 0.01759 = 0.02951 -0.00022 0.00708 -0.00069 AFIX 43 H8 2 0.634702 0.641053 0.324937 11.00000 -1.20000 AFIX 0 C9 1 0.744305 0.761766 0.288108 11.00000 0.02777 0.02000 = 0.02555 0.00129 0.00506 -0.00025 C10 1 0.832215 0.686010 0.255746 11.00000 0.02498 0.02312 = 0.02536 -0.00098 0.00587 -0.00099 C11 1 0.832651 0.570084 0.287564 11.00000 0.03452 0.02578 = 0.06479 0.00861 0.02508 0.00257 AFIX 43 H11 2 0.773388 0.536206 0.325584 11.00000 -1.20000 AFIX 0 C12 1 0.918870 0.503611 0.264233 11.00000 0.04150 0.02510 = 0.07698 0.00802 0.02848 0.00505 AFIX 43 H12 2 0.918733 0.424383 0.287611 11.00000 -1.20000 AFIX 0 C13 1 1.005265 0.550986 0.207320 11.00000 0.02697 0.03310 = 0.04434 -0.00186 0.01158 0.00431 AFIX 43 H13 2 1.064797 0.505057 0.192867 11.00000 -1.20000 AFIX 0 C14 1 1.003984 0.665847 0.171743 11.00000 0.02932 0.03456 = 0.04117 -0.00035 0.01456 -0.00419 AFIX 43 H14 2 1.062182 0.698996 0.129939 11.00000 -1.20000 AFIX 0 C15 1 0.918459 0.733028 0.196583 11.00000 0.03066 0.02345 = 0.03722 0.00046 0.00988 -0.00390 AFIX 43 H15 2 0.918791 0.812204 0.172873 11.00000 -1.20000 AFIX 0 HKLF 4 REM r20200716a_a.res in P2(1)/c REM wR2 = 0.1232, GooF = S = 1.044, Restrained GooF = 1.044 for all data REM R1 = 0.0474 for 1836 Fo > 4sig(Fo) and 0.0607 for all 2276 data REM 155 parameters refined using 0 restraints END WGHT 0.0543 0.4038 REM Instructions for potential hydrogen bonds HTAB O1 O2 REM Highest difference peak 0.274, deepest hole -0.192, 1-sigma level 0.039 Q1 1 0.6981 0.9000 0.3056 11.00000 0.05 0.27 Q2 1 0.7821 0.7198 0.2323 11.00000 0.05 0.22 Q3 1 0.5008 0.7789 0.3441 11.00000 0.05 0.22 Q4 1 0.4215 0.7989 0.3853 11.00000 0.05 0.21 Q5 1 0.5965 0.7583 0.3096 11.00000 0.05 0.21 Q6 1 0.9737 0.6993 0.2462 11.00000 0.05 0.18 Q7 1 0.5193 0.7684 0.3918 11.00000 0.05 0.17 Q8 1 0.8618 0.7049 0.2067 11.00000 0.05 0.17 Q9 1 0.6236 0.7568 0.3739 11.00000 0.05 0.17 Q10 1 0.6765 0.7456 0.2666 11.00000 0.05 0.17 Q11 1 0.7987 0.5426 0.4209 11.00000 0.05 0.16 Q12 1 0.9426 0.5373 0.1922 11.00000 0.05 0.15 Q13 1 0.8657 0.5430 0.2139 11.00000 0.05 0.15 Q14 1 0.3642 0.6355 0.3616 11.00000 0.05 0.14 Q15 1 0.4405 0.7195 0.3464 11.00000 0.05 0.14 Q16 1 0.8564 0.8762 0.3160 11.00000 0.05 0.13 Q17 1 0.8200 0.6377 0.2331 11.00000 0.05 0.13 Q18 1 0.9394 0.6917 0.1232 11.00000 0.05 0.13 Q19 1 0.2674 0.7528 0.4065 11.00000 0.05 0.13 Q20 1 0.6214 0.6620 0.2725 11.00000 0.05 0.12 ; _shelx_res_checksum 68507 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.680 _oxdiff_exptl_absorpt_empirical_full_min 0.694 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 O1 O 0.58570(9) 0.90420(9) 0.35967(17) 0.0347(3) Uani 1 1 d . . . . . H1 H 0.645984 0.917282 0.334198 0.052 Uiso 1 1 calc GR . . . . O2 O 0.76146(9) 0.86971(8) 0.28266(15) 0.0323(3) Uani 1 1 d . . . . . C1 C 0.39384(13) 0.84078(13) 0.4376(2) 0.0293(4) Uani 1 1 d . . . . . H1A H 0.412979 0.918880 0.437482 0.035 Uiso 1 1 calc R . . . . C2 C 0.29531(13) 0.80928(14) 0.4752(2) 0.0332(4) Uani 1 1 d . . . . . H2 H 0.247412 0.865716 0.501605 0.040 Uiso 1 1 calc R . . . . C3 C 0.26669(13) 0.69571(14) 0.4743(2) 0.0325(4) Uani 1 1 d . . . . . H3 H 0.199030 0.674154 0.499638 0.039 Uiso 1 1 calc R . . . . C4 C 0.33666(13) 0.61367(13) 0.4366(2) 0.0320(4) Uani 1 1 d . . . . . H4 H 0.317018 0.535684 0.436001 0.038 Uiso 1 1 calc R . . . . C5 C 0.43516(13) 0.64478(13) 0.3996(2) 0.0287(4) Uani 1 1 d . . . . . H5 H 0.482889 0.587979 0.373727 0.034 Uiso 1 1 calc R . . . . C6 C 0.46484(12) 0.75869(12) 0.40005(19) 0.0239(3) Uani 1 1 d . . . . . C7 C 0.56926(12) 0.79548(12) 0.35971(19) 0.0244(3) Uani 1 1 d . . . . . C8 C 0.64736(12) 0.72063(12) 0.32439(19) 0.0243(3) Uani 1 1 d . . . . . H8 H 0.634702 0.641053 0.324937 0.029 Uiso 1 1 calc R . . . . C9 C 0.74430(12) 0.76177(12) 0.28811(19) 0.0246(3) Uani 1 1 d . . . . . C10 C 0.83221(12) 0.68601(12) 0.25575(19) 0.0245(3) Uani 1 1 d . . . . . C11 C 0.83265(14) 0.57008(14) 0.2876(3) 0.0395(4) Uani 1 1 d . . . . . H11 H 0.773388 0.536206 0.325584 0.047 Uiso 1 1 calc R . . . . C12 C 0.91887(15) 0.50361(15) 0.2642(3) 0.0454(5) Uani 1 1 d . . . . . H12 H 0.918733 0.424383 0.287611 0.055 Uiso 1 1 calc R . . . . C13 C 1.00527(13) 0.55099(14) 0.2073(2) 0.0343(4) Uani 1 1 d . . . . . H13 H 1.064797 0.505057 0.192867 0.041 Uiso 1 1 calc R . . . . C14 C 1.00398(13) 0.66585(14) 0.1717(2) 0.0340(4) Uani 1 1 d . . . . . H14 H 1.062182 0.698996 0.129939 0.041 Uiso 1 1 calc R . . . . C15 C 0.91846(13) 0.73303(13) 0.1966(2) 0.0301(4) Uani 1 1 d . . . . . H15 H 0.918791 0.812204 0.172873 0.036 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0340(7) 0.0179(6) 0.0565(8) -0.0020(5) 0.0189(6) -0.0014(4) O2 0.0340(6) 0.0180(5) 0.0473(7) 0.0019(4) 0.0144(5) -0.0025(4) C1 0.0300(8) 0.0246(8) 0.0330(8) -0.0036(6) 0.0067(6) 0.0019(6) C2 0.0288(8) 0.0349(9) 0.0373(9) -0.0047(7) 0.0102(7) 0.0059(7) C3 0.0268(8) 0.0399(9) 0.0322(9) -0.0016(7) 0.0094(7) -0.0027(7) C4 0.0348(9) 0.0267(8) 0.0359(9) -0.0019(6) 0.0109(7) -0.0048(7) C5 0.0302(8) 0.0226(8) 0.0348(9) -0.0008(6) 0.0105(7) 0.0002(6) C6 0.0250(8) 0.0234(7) 0.0227(7) -0.0017(6) 0.0042(6) 0.0014(6) C7 0.0290(8) 0.0192(7) 0.0241(8) -0.0001(5) 0.0042(6) -0.0015(6) C8 0.0262(8) 0.0176(7) 0.0295(8) -0.0002(6) 0.0071(6) -0.0007(6) C9 0.0278(8) 0.0200(7) 0.0256(8) 0.0013(6) 0.0051(6) -0.0002(6) C10 0.0250(8) 0.0231(8) 0.0254(8) -0.0010(6) 0.0059(6) -0.0010(6) C11 0.0345(9) 0.0258(8) 0.0648(12) 0.0086(8) 0.0251(9) 0.0026(7) C12 0.0415(10) 0.0251(9) 0.0770(14) 0.0080(8) 0.0285(10) 0.0051(7) C13 0.0270(8) 0.0331(9) 0.0443(10) -0.0019(7) 0.0116(7) 0.0043(7) C14 0.0293(8) 0.0346(9) 0.0412(9) -0.0003(7) 0.0146(7) -0.0042(7) C15 0.0307(8) 0.0234(8) 0.0372(9) 0.0005(6) 0.0099(7) -0.0039(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 '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 C7 O1 H1 109.5 . . ? C2 C1 H1A 119.8 . . ? C2 C1 C6 120.37(15) . . ? C6 C1 H1A 119.8 . . ? C1 C2 H2 120.0 . . ? C3 C2 C1 120.06(15) . . ? C3 C2 H2 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.90(15) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 119.9 . . ? C3 C4 C5 120.19(15) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.44(15) . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.04(14) . . ? C1 C6 C7 118.91(13) . . ? C5 C6 C7 122.04(13) . . ? O1 C7 C6 115.93(13) . . ? O1 C7 C8 120.33(14) . . ? C8 C7 C6 123.74(13) . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.46(13) . . ? C9 C8 H8 119.8 . . ? O2 C9 C8 120.47(14) . . ? O2 C9 C10 116.67(13) . . ? C8 C9 C10 122.86(13) . . ? C11 C10 C9 122.18(14) . . ? C11 C10 C15 118.76(14) . . ? C15 C10 C9 119.04(13) . . ? C10 C11 H11 119.9 . . ? C12 C11 C10 120.29(16) . . ? C12 C11 H11 119.9 . . ? C11 C12 H12 119.6 . . ? C13 C12 C11 120.77(16) . . ? C13 C12 H12 119.6 . . ? C12 C13 H13 120.4 . . ? C14 C13 C12 119.13(15) . . ? C14 C13 H13 120.4 . . ? C13 C14 H14 119.8 . . ? C13 C14 C15 120.36(15) . . ? C15 C14 H14 119.8 . . ? C10 C15 H15 119.7 . . ? C14 C15 C10 120.67(14) . . ? C14 C15 H15 119.7 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.8400 . ? O1 C7 1.2959(17) . ? O2 C9 1.2907(17) . ? C1 H1A 0.9500 . ? C1 C2 1.386(2) . ? C1 C6 1.391(2) . ? C2 H2 0.9500 . ? C2 C3 1.383(2) . ? C3 H3 0.9500 . ? C3 C4 1.382(2) . ? C4 H4 0.9500 . ? C4 C5 1.383(2) . ? C5 H5 0.9500 . ? C5 C6 1.391(2) . ? C6 C7 1.482(2) . ? C7 C8 1.392(2) . ? C8 H8 0.9500 . ? C8 C9 1.398(2) . ? C9 C10 1.485(2) . ? C10 C11 1.386(2) . ? C10 C15 1.387(2) . ? C11 H11 0.9500 . ? C11 C12 1.381(2) . ? C12 H12 0.9500 . ? C12 C13 1.381(2) . ? C13 H13 0.9500 . ? C13 C14 1.379(2) . ? C14 H14 0.9500 . ? C14 C15 1.383(2) . ? C15 H15 0.9500 . ? 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 O1 C7 C8 C9 -0.1(2) . . . . ? O2 C9 C10 C11 168.64(15) . . . . ? O2 C9 C10 C15 -9.5(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C1 C6 C7 O1 -1.2(2) . . . . ? C1 C6 C7 C8 178.45(14) . . . . ? C2 C1 C6 C5 0.4(2) . . . . ? C2 C1 C6 C7 179.75(14) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C4 C5 C6 C7 -179.50(14) . . . . ? C5 C6 C7 O1 178.12(14) . . . . ? C5 C6 C7 C8 -2.3(2) . . . . ? C6 C1 C2 C3 -0.5(2) . . . . ? C6 C7 C8 C9 -179.73(13) . . . . ? C7 C8 C9 O2 -1.7(2) . . . . ? C7 C8 C9 C10 177.78(13) . . . . ? C8 C9 C10 C11 -10.9(2) . . . . ? C8 C9 C10 C15 171.05(14) . . . . ? C9 C10 C11 C12 -176.69(17) . . . . ? C9 C10 C15 C14 177.41(14) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C10 C15 C14 -0.8(2) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C15 1.4(3) . . . . ? C13 C14 C15 C10 -0.7(2) . . . . ? C15 C10 C11 C12 1.4(3) . . . . ?