#------------------------------------------------------------------------------ #$Date: 2024-02-04 13:39:27 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289450 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247790.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_7247790 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 orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-07-27 _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.6333(7) _cell_length_b 10.6401(7) _cell_length_c 24.273(2) _cell_measurement_reflns_used 4595 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 32.6760 _cell_measurement_theta_min 2.8720 _cell_volume 2229.7(3) _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -120.00 60.00 1.00 2.00 -- -30.00 45.00 0.00 180 2 \w -120.00 30.00 1.00 2.00 -- -30.00 45.00 90.00 150 3 \w -120.00 0.00 1.00 2.00 -- -30.00 45.00 180.00 120 ; _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 -0.0150638000 _diffrn_orient_matrix_UB_12 0.0187134000 _diffrn_orient_matrix_UB_13 -0.0275195000 _diffrn_orient_matrix_UB_21 -0.0069001000 _diffrn_orient_matrix_UB_22 -0.0639550000 _diffrn_orient_matrix_UB_23 -0.0078622000 _diffrn_orient_matrix_UB_31 -0.0804563000 _diffrn_orient_matrix_UB_32 0.0020440000 _diffrn_orient_matrix_UB_33 0.0059120000 _diffrn_radiation_monochromator confocal _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 16650 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.373 _diffrn_reflns_theta_min 1.678 _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 0.54550 _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 1.336 _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.227 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2281 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0518 _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^)+(0.0458P)^2^+1.0894P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1125 _refine_ls_wR_factor_ref 0.1260 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1782 _reflns_number_total 2281 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00856h2.cif _cod_data_source_block r20200716b _cod_depositor_comments 'Adding full bibliography for 7247790--7247791.cif.' _cod_database_code 7247790 _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 99.81 _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 r20200716b_a.res in Pbca r20200716b.res created by SHELXL-2018/3 at 09:56:15 on 27-Jul-2020 REM Old TITL r20200716b in Pbca REM SHELXT solution in Pbca: R1 0.150, Rweak 0.282, Alpha 0.017 REM 0.553 for 357 systematic absences, Orientation as input REM Formula found by SHELXT: C15 O2 CELL 0.71073 8.6333 10.6401 24.2729 90 90 90 ZERR 8 0.0007 0.0007 0.0021 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O UNIT 120 96 16 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 REM REM REM WGHT 0.045800 1.089400 FVAR 0.84305 O1 3 0.708683 0.696545 0.637062 11.00000 0.03547 0.02413 = 0.02973 -0.00121 -0.00130 -0.00375 AFIX 147 H1 2 0.765411 0.724089 0.611671 11.00000 -1.50000 AFIX 0 O2 3 0.839139 0.707956 0.547690 11.00000 0.03399 0.02351 = 0.03049 0.00220 -0.00304 -0.00540 C1 1 0.476591 0.611603 0.704331 11.00000 0.02684 0.03025 = 0.02463 -0.00402 -0.00393 0.00406 AFIX 43 H1A 2 0.510014 0.696346 0.707580 11.00000 -1.20000 AFIX 0 C2 1 0.375415 0.562559 0.742830 11.00000 0.02964 0.04163 = 0.02225 -0.00659 -0.00149 0.00665 AFIX 43 H2 2 0.339282 0.613841 0.772178 11.00000 -1.20000 AFIX 0 C3 1 0.326477 0.439046 0.738823 11.00000 0.03028 0.04007 = 0.02494 0.00119 0.00274 0.00208 AFIX 43 H3 2 0.257392 0.405283 0.765450 11.00000 -1.20000 AFIX 0 C4 1 0.378941 0.364779 0.695665 11.00000 0.03012 0.02852 = 0.02960 0.00052 0.00164 0.00121 AFIX 43 H4 2 0.345910 0.279852 0.692857 11.00000 -1.20000 AFIX 0 C5 1 0.479239 0.413926 0.656670 11.00000 0.02808 0.02773 = 0.02422 -0.00184 0.00162 0.00544 AFIX 43 H5 2 0.513528 0.362832 0.626981 11.00000 -1.20000 AFIX 0 C6 1 0.530221 0.538086 0.660744 11.00000 0.02174 0.02526 = 0.02254 -0.00040 -0.00376 0.00456 C7 1 0.638262 0.593708 0.620352 11.00000 0.02243 0.02127 = 0.02739 0.00168 -0.00629 0.00389 C8 1 0.666946 0.545273 0.568585 11.00000 0.02450 0.02139 = 0.02770 -0.00155 -0.00160 -0.00059 AFIX 43 H8 2 0.614748 0.471437 0.556771 11.00000 -1.20000 AFIX 0 C9 1 0.774169 0.605430 0.532955 11.00000 0.02409 0.02221 = 0.02601 0.00309 -0.00421 0.00315 C10 1 0.815248 0.553865 0.478206 11.00000 0.02084 0.02326 = 0.02590 0.00559 -0.00165 0.00300 C11 1 0.755997 0.439492 0.459521 11.00000 0.02244 0.02848 = 0.02448 0.00458 0.00031 -0.00137 AFIX 43 H11 2 0.684717 0.394120 0.481736 11.00000 -1.20000 AFIX 0 C12 1 0.800266 0.391658 0.408886 11.00000 0.02704 0.02655 = 0.02787 0.00083 -0.00082 -0.00299 AFIX 43 H12 2 0.759961 0.313426 0.396626 11.00000 -1.20000 AFIX 0 C13 1 0.903389 0.457765 0.376012 11.00000 0.03035 0.03138 = 0.02641 0.00217 0.00269 0.00300 AFIX 43 H13 2 0.932504 0.425446 0.341028 11.00000 -1.20000 AFIX 0 C14 1 0.963749 0.570704 0.394201 11.00000 0.02415 0.03081 = 0.03097 0.00925 0.00370 -0.00002 AFIX 43 H14 2 1.034852 0.615693 0.371766 11.00000 -1.20000 AFIX 0 C15 1 0.920936 0.618389 0.444957 11.00000 0.02423 0.02480 = 0.03288 0.00467 -0.00073 -0.00014 AFIX 43 H15 2 0.963691 0.695652 0.457346 11.00000 -1.20000 AFIX 0 HKLF 4 REM r20200716b_a.res in Pbca REM wR2 = 0.1260, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0518 for 1782 Fo > 4sig(Fo) and 0.0690 for all 2281 data REM 155 parameters refined using 0 restraints END WGHT 0.0458 1.0894 REM Instructions for potential hydrogen bonds HTAB O1 O2 REM Highest difference peak 0.227, deepest hole -0.307, 1-sigma level 0.052 Q1 1 0.8071 0.7187 0.5805 11.00000 0.05 0.23 Q2 1 0.3550 0.4610 0.8024 11.00000 0.05 0.19 Q3 1 0.9966 0.4341 0.2954 11.00000 0.05 0.19 Q4 1 0.7569 0.5214 0.4610 11.00000 0.05 0.16 Q5 1 0.6801 0.5540 0.5980 11.00000 0.05 0.16 Q6 1 0.9545 0.5014 0.4000 11.00000 0.05 0.16 Q7 1 0.8883 0.4185 0.3985 11.00000 0.05 0.16 Q8 1 0.1788 0.4461 0.6990 11.00000 0.05 0.15 Q9 1 0.1795 0.2984 0.6969 11.00000 0.05 0.15 Q10 1 0.4082 0.4712 0.7506 11.00000 0.05 0.15 Q11 1 1.0206 0.5351 0.3006 11.00000 0.05 0.15 Q12 1 1.0401 0.6779 0.3256 11.00000 0.05 0.15 Q13 1 0.2165 0.1957 0.7004 11.00000 0.05 0.15 Q14 1 0.3958 0.5795 0.7616 11.00000 0.05 0.15 Q15 1 0.9411 0.3330 0.3003 11.00000 0.05 0.14 Q16 1 0.1626 0.3795 0.6788 11.00000 0.05 0.14 Q17 1 0.4642 0.2994 0.5909 11.00000 0.05 0.14 Q18 1 0.9191 0.6019 0.4186 11.00000 0.05 0.14 Q19 1 0.8545 0.4574 0.3147 11.00000 0.05 0.14 Q20 1 0.9443 0.4851 0.3161 11.00000 0.05 0.13 ; _shelx_res_checksum 346 _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 1.414 _oxdiff_exptl_absorpt_empirical_full_min 0.568 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 O1 O 0.70868(16) 0.69654(12) 0.63706(5) 0.0298(3) Uani 1 1 d . . . . . H1 H 0.765411 0.724089 0.611671 0.045 Uiso 1 1 calc GR . . . . O2 O 0.83914(15) 0.70796(11) 0.54769(5) 0.0293(3) Uani 1 1 d . . . . . C1 C 0.4766(2) 0.61160(18) 0.70433(8) 0.0272(4) Uani 1 1 d . . . . . H1A H 0.510014 0.696346 0.707580 0.033 Uiso 1 1 calc R . . . . C2 C 0.3754(2) 0.56256(18) 0.74283(8) 0.0312(5) Uani 1 1 d . . . . . H2 H 0.339282 0.613841 0.772178 0.037 Uiso 1 1 calc R . . . . C3 C 0.3265(2) 0.43905(19) 0.73882(8) 0.0318(5) Uani 1 1 d . . . . . H3 H 0.257392 0.405283 0.765450 0.038 Uiso 1 1 calc R . . . . C4 C 0.3789(2) 0.36478(18) 0.69566(8) 0.0294(4) Uani 1 1 d . . . . . H4 H 0.345910 0.279852 0.692857 0.035 Uiso 1 1 calc R . . . . C5 C 0.4792(2) 0.41393(17) 0.65667(7) 0.0267(4) Uani 1 1 d . . . . . H5 H 0.513528 0.362832 0.626981 0.032 Uiso 1 1 calc R . . . . C6 C 0.5302(2) 0.53809(16) 0.66074(7) 0.0232(4) Uani 1 1 d . . . . . C7 C 0.6383(2) 0.59371(16) 0.62035(8) 0.0237(4) Uani 1 1 d . . . . . C8 C 0.6669(2) 0.54527(16) 0.56859(7) 0.0245(4) Uani 1 1 d . . . . . H8 H 0.614748 0.471437 0.556771 0.029 Uiso 1 1 calc R . . . . C9 C 0.7742(2) 0.60543(16) 0.53296(7) 0.0241(4) Uani 1 1 d . . . . . C10 C 0.8152(2) 0.55387(16) 0.47821(7) 0.0233(4) Uani 1 1 d . . . . . C11 C 0.7560(2) 0.43949(17) 0.45952(7) 0.0251(4) Uani 1 1 d . . . . . H11 H 0.684717 0.394120 0.481736 0.030 Uiso 1 1 calc R . . . . C12 C 0.8003(2) 0.39166(17) 0.40889(8) 0.0272(4) Uani 1 1 d . . . . . H12 H 0.759961 0.313426 0.396626 0.033 Uiso 1 1 calc R . . . . C13 C 0.9034(2) 0.45776(18) 0.37601(8) 0.0294(4) Uani 1 1 d . . . . . H13 H 0.932504 0.425446 0.341028 0.035 Uiso 1 1 calc R . . . . C14 C 0.9637(2) 0.57070(17) 0.39420(8) 0.0286(4) Uani 1 1 d . . . . . H14 H 1.034852 0.615693 0.371766 0.034 Uiso 1 1 calc R . . . . C15 C 0.9209(2) 0.61839(17) 0.44496(8) 0.0273(4) Uani 1 1 d . . . . . H15 H 0.963691 0.695652 0.457346 0.033 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 0.0355(8) 0.0241(7) 0.0297(7) -0.0012(6) -0.0013(6) -0.0037(6) O2 0.0340(8) 0.0235(7) 0.0305(7) 0.0022(5) -0.0030(6) -0.0054(6) C1 0.0268(10) 0.0302(9) 0.0246(9) -0.0040(8) -0.0039(8) 0.0041(8) C2 0.0296(11) 0.0416(11) 0.0222(10) -0.0066(8) -0.0015(8) 0.0066(9) C3 0.0303(11) 0.0401(11) 0.0249(10) 0.0012(8) 0.0027(8) 0.0021(9) C4 0.0301(10) 0.0285(10) 0.0296(10) 0.0005(8) 0.0016(8) 0.0012(8) C5 0.0281(10) 0.0277(9) 0.0242(10) -0.0018(8) 0.0016(8) 0.0054(8) C6 0.0217(9) 0.0253(9) 0.0225(9) -0.0004(7) -0.0038(7) 0.0046(7) C7 0.0224(9) 0.0213(8) 0.0274(10) 0.0017(7) -0.0063(7) 0.0039(7) C8 0.0245(9) 0.0214(9) 0.0277(10) -0.0016(7) -0.0016(8) -0.0006(7) C9 0.0241(9) 0.0222(9) 0.0260(9) 0.0031(7) -0.0042(7) 0.0032(7) C10 0.0208(9) 0.0233(9) 0.0259(9) 0.0056(7) -0.0017(7) 0.0030(7) C11 0.0224(9) 0.0285(9) 0.0245(9) 0.0046(7) 0.0003(8) -0.0014(8) C12 0.0270(10) 0.0266(9) 0.0279(10) 0.0008(8) -0.0008(8) -0.0030(8) C13 0.0303(10) 0.0314(10) 0.0264(10) 0.0022(8) 0.0027(8) 0.0030(8) C14 0.0241(10) 0.0308(10) 0.0310(10) 0.0092(8) 0.0037(8) 0.0000(8) C15 0.0242(10) 0.0248(9) 0.0329(10) 0.0047(8) -0.0007(8) -0.0001(8) 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 119.6 . . ? C2 C1 C6 120.74(18) . . ? C6 C1 H1A 119.6 . . ? C1 C2 H2 119.9 . . ? C1 C2 C3 120.28(18) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 120.2 . . ? C2 C3 C4 119.60(18) . . ? C4 C3 H3 120.2 . . ? C3 C4 H4 119.8 . . ? C5 C4 C3 120.31(18) . . ? C5 C4 H4 119.8 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.39(17) . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.67(17) . . ? C1 C6 C7 119.24(16) . . ? C5 C6 C7 122.09(16) . . ? O1 C7 C6 114.86(16) . . ? O1 C7 C8 120.54(17) . . ? C8 C7 C6 124.60(16) . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.22(16) . . ? C9 C8 H8 119.9 . . ? O2 C9 C8 120.05(16) . . ? O2 C9 C10 117.54(16) . . ? C8 C9 C10 122.41(16) . . ? C11 C10 C9 121.79(16) . . ? C11 C10 C15 118.66(17) . . ? C15 C10 C9 119.49(16) . . ? C10 C11 H11 119.7 . . ? C12 C11 C10 120.53(17) . . ? C12 C11 H11 119.7 . . ? C11 C12 H12 119.9 . . ? C11 C12 C13 120.11(17) . . ? C13 C12 H12 119.9 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 119.94(18) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.19(18) . . ? C15 C14 H14 119.9 . . ? C10 C15 H15 119.7 . . ? C14 C15 C10 120.57(18) . . ? 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 1.316(2) . ? O2 C9 1.278(2) . ? C1 H1A 0.9500 . ? C1 C2 1.381(3) . ? C1 C6 1.395(2) . ? C2 H2 0.9500 . ? C2 C3 1.384(3) . ? C3 H3 0.9500 . ? C3 C4 1.388(3) . ? C4 H4 0.9500 . ? C4 C5 1.385(3) . ? C5 H5 0.9500 . ? C5 C6 1.396(2) . ? C6 C7 1.477(3) . ? C7 C8 1.380(3) . ? C8 H8 0.9500 . ? C8 C9 1.419(3) . ? C9 C10 1.481(3) . ? C10 C11 1.396(2) . ? C10 C15 1.398(2) . ? C11 H11 0.9500 . ? C11 C12 1.384(3) . ? C12 H12 0.9500 . ? C12 C13 1.387(3) . ? C13 H13 0.9500 . ? C13 C14 1.382(3) . ? C14 H14 0.9500 . ? C14 C15 1.383(3) . ? 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 0.6(3) . . . . ? O2 C9 C10 C11 176.97(16) . . . . ? O2 C9 C10 C15 -0.4(2) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C6 C7 O1 18.2(2) . . . . ? C1 C6 C7 C8 -161.70(17) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? C2 C1 C6 C7 179.98(16) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C4 C5 C6 C7 179.41(17) . . . . ? C5 C6 C7 O1 -162.01(16) . . . . ? C5 C6 C7 C8 18.1(3) . . . . ? C6 C1 C2 C3 0.4(3) . . . . ? C6 C7 C8 C9 -179.48(16) . . . . ? C7 C8 C9 O2 -3.3(3) . . . . ? C7 C8 C9 C10 176.77(16) . . . . ? C8 C9 C10 C11 -3.1(3) . . . . ? C8 C9 C10 C15 179.52(16) . . . . ? C9 C10 C11 C12 -177.94(16) . . . . ? C9 C10 C15 C14 178.55(16) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C10 C15 C14 1.1(3) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C10 -0.6(3) . . . . ? C15 C10 C11 C12 -0.5(3) . . . . ?