#------------------------------------------------------------------------------ #$Date: 2023-12-06 17:50:21 +0200 (Wed, 06 Dec 2023) $ #$Revision: 288091 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247707.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_7247707 loop_ _publ_author_name 'Por\;eba, Tomasz' 'Kicior, Inga' _publ_section_title ; Pressure-freezing of dodecane: exploring the crystal structures, formation kinetics and phase diagrams for colossal barocaloric effects in n-alkanes ; _journal_issue 47 _journal_name_full 'RSC Advances' _journal_page_first 33305 _journal_page_last 33317 _journal_paper_doi 10.1039/D3RA06957E _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C11 H24' _chemical_formula_sum 'C11 H24' _chemical_formula_weight 156.30 _chemical_name_common undecane _chemical_name_systematic n-undecane _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 2023-07-12 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2023-07-12 deposited with the CCDC. 2023-11-03 downloaded from the CCDC. ; _cell_angle_alpha 93.609(19) _cell_angle_beta 90.41(2) _cell_angle_gamma 107.274(9) _cell_formula_units_Z 2 _cell_length_a 4.1808(5) _cell_length_b 4.7113(3) _cell_length_c 29.53(2) _cell_measurement_pressure 170000 _cell_measurement_reflns_used 147 _cell_measurement_temperature 295 _cell_measurement_theta_max 16.1090 _cell_measurement_theta_min 2.6160 _cell_volume 554.1(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment Helium _diffrn_ambient_pressure 170000 _diffrn_ambient_temperature 295 _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 13.3333 _diffrn_detector_type 'Eiger 9M CdTe' _diffrn_measured_fraction_theta_full 0.268 _diffrn_measured_fraction_theta_max 0.261 _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 -32.00 32.00 0.50 1.00 -- 0.00 0.00 0.00 128 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'esperanto-CrysAlisPro-abstract goniometer imported esperanto images' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'diamond anvil cell' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0134237000 _diffrn_orient_matrix_UB_12 0.0048137000 _diffrn_orient_matrix_UB_13 0.0137352000 _diffrn_orient_matrix_UB_21 -0.0273326000 _diffrn_orient_matrix_UB_22 -0.0911428000 _diffrn_orient_matrix_UB_23 -0.0001327000 _diffrn_orient_matrix_UB_31 0.0981195000 _diffrn_orient_matrix_UB_32 0.0037707000 _diffrn_orient_matrix_UB_33 0.0022379000 _diffrn_radiation_monochromator synchrotron _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.410 _diffrn_reflns_av_R_equivalents 0.0054 _diffrn_reflns_av_unetI/netI 0.0122 _diffrn_reflns_Laue_measured_fraction_full 0.268 _diffrn_reflns_Laue_measured_fraction_max 0.261 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 867 _diffrn_reflns_point_group_measured_fraction_full 0.268 _diffrn_reflns_point_group_measured_fraction_max 0.261 _diffrn_reflns_theta_full 14.241 _diffrn_reflns_theta_max 14.802 _diffrn_reflns_theta_min 2.618 _diffrn_source synchrotron _exptl_absorpt_coefficient_mu 0.025 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58199 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022) 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 0.937 _exptl_crystal_description plate _exptl_crystal_F_000 180 _exptl_crystal_recrystallization_method 'in-situ recrystallization from melt at high pressure in diamond anvil cell' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.072 _refine_diff_density_min -0.070 _refine_diff_density_rms 0.023 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 102 _refine_ls_number_reflns 586 _refine_ls_number_restraints 80 _refine_ls_restrained_S_all 0.972 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0539 _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^)+(0.1112P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1564 _refine_ls_wR_factor_ref 0.1951 _reflns_Friedel_coverage 0.000 _reflns_number_gt 253 _reflns_number_total 586 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06957e3.cif _cod_data_source_block undecane _cod_depositor_comments ; The following automatic conversions were performed: data name '_diffrn_measurement_specimen_suport' was replaced with '_diffrn_measurement_specimen_support' as specified in the replacement file 'data/replacement-values/replacement_tags.lst'. Automatic conversion script Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas ; _cod_database_code 7247707 _shelx_shelxl_version_number 2017/1 _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 0.999 _shelx_estimated_absorpt_t_min 0.994 _diffrn_orient_matrix_axis[1] matrixX _diffrn_orient_matrix_axis[2] matrixY _diffrn_orient_matrix_axis[3] matrixZ _reflns_odcompleteness_completeness 15.49 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 21.01 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C11-C10 = C9-C10 = C9-C8 = C8-C7 = C7-C6 = C6-C5 = C5-C4 = C4-C3 = C3-C2 = C2- C1 1.52 with sigma of 0.005 C1-C2 \\sim C2-C3 with sigma of 0.02 C9-C10 \\sim C10-C11 with sigma of 0.02 C3-C4 \\sim C4-C5 with sigma of 0.02 C5-C6 \\sim C6-C7 with sigma of 0.02 C7-C8 \\sim C8-C9 with sigma of 0.02 C9-C8 \\sim C8-C7 with sigma of 0.02 C7-C6 \\sim C7-C8 with sigma of 0.02 C10-C9 \\sim C9-C8 with sigma of 0.02 C5-C6 \\sim C5-C4 with sigma of 0.02 C3-C4 \\sim C2-C3 with sigma of 0.02 3. Rigid bond restraints C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Uiso/Uaniso restraints and constraints Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 5.a Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C4(H4A,H4B), C8(H8A,H8B), C3(H3A,H3B), C9(H9A,H9B), C10(H10A, H10B), C7(H7A,H7B), C5(H5A,H5B), C2(H2A,H2B) 5.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C11(H11A,H11B,H11C) ; _shelx_res_file ; TITL 0003_0001_a.res in P-1 undecane.res created by SHELXL-2017/1 at 16:52:27 on 12-Jul-2023 REM Old TITL 0003_0001 in P-1 REM SHELXT solution in P-1: R1 0.284, Rweak 0.002, Alpha 0.131 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C11 CELL 0.41 4.180848 4.711303 29.529974 93.6092 90.4121 107.2737 ZERR 2 0.000483 0.000349 0.019758 0.019 0.0225 0.0086 LATT 1 SFAC C H DISP C -0.0011 0.0005 5.0796 DISP H 0 0 0.5971 UNIT 22 48 DELU C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 ISOR 0.01 0.02 C11 SADI C1 C2 C2 C3 SADI C9 C10 C10 C11 SADI C3 C4 C4 C5 SADI C5 C6 C6 C7 SADI C7 C8 C8 C9 SADI C9 C8 C8 C7 SADI C7 C6 C7 C8 SADI C10 C9 C9 C8 SADI C5 C6 C5 C4 SADI C3 C4 C2 C3 DFIX 1.52 0.005 C11 C10 C9 C10 C9 C8 C8 C7 C7 C6 C6 C5 C5 C4 C4 C3 C3 C2 C2 C1 L.S. 4 0 0 PLAN 6 SIZE 0.12 0.22 0.02 TEMP 21.85 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta SHEL 0.8 1000 OMIT -4 -1 6 REM REM REM WGHT 0.111200 FVAR 15.95135 C6 1 0.260640 0.557830 0.745850 11.00000 0.06487 0.04884 = 0.04200 -0.00179 -0.00327 0.01436 AFIX 23 H6A 2 0.045131 0.419585 0.736254 11.00000 -1.20000 H6B 2 0.408819 0.441190 0.752688 11.00000 -1.20000 AFIX 0 C4 1 0.448944 0.573896 0.663888 11.00000 0.07078 0.04892 = 0.05081 -0.00542 -0.00006 0.01506 AFIX 23 H4A 2 0.233964 0.435730 0.654053 11.00000 -1.20000 H4B 2 0.596829 0.456997 0.670734 11.00000 -1.20000 AFIX 0 C8 1 0.075955 0.545278 0.827763 11.00000 0.06747 0.05101 = 0.04858 0.00232 0.01594 0.01361 AFIX 23 H8A 2 -0.140121 0.407167 0.818378 11.00000 -1.20000 H8B 2 0.224040 0.428623 0.834638 11.00000 -1.20000 AFIX 0 C3 1 0.591487 0.761930 0.624956 11.00000 0.06669 0.04945 = 0.04668 -0.00214 -0.00144 0.01547 AFIX 23 H3A 2 0.806955 0.899292 0.634783 11.00000 -1.20000 H3B 2 0.444290 0.879819 0.618296 11.00000 -1.20000 AFIX 0 C9 1 0.033499 0.722126 0.870342 11.00000 0.07263 0.05695 = 0.04014 0.00646 0.00868 0.01589 AFIX 23 H9A 2 -0.116263 0.837285 0.863503 11.00000 -1.20000 H9B 2 0.249200 0.861696 0.879514 11.00000 -1.20000 AFIX 0 C10 1 -0.102901 0.537145 0.909738 11.00000 0.08613 0.07497 = 0.04822 0.00898 0.01983 0.02533 AFIX 23 H10A 2 0.045510 0.420334 0.916375 11.00000 -1.20000 H10B 2 -0.319781 0.399108 0.900694 11.00000 -1.20000 AFIX 0 C7 1 0.215644 0.731674 0.788630 11.00000 0.06621 0.04845 = 0.04138 0.00170 0.00492 0.01500 AFIX 23 H7A 2 0.067030 0.847894 0.781785 11.00000 -1.20000 H7B 2 0.431074 0.870378 0.798145 11.00000 -1.20000 AFIX 0 C5 1 0.401086 0.744868 0.706919 11.00000 0.06542 0.04802 = 0.04618 -0.00287 0.00554 0.01387 AFIX 23 H5A 2 0.615858 0.883800 0.716653 11.00000 -1.20000 H5B 2 0.252284 0.860960 0.700097 11.00000 -1.20000 AFIX 0 C1 1 0.786771 0.782178 0.542738 11.00000 0.09110 0.07873 = 0.05200 0.00283 0.01740 0.02309 AFIX 137 H1A 2 0.816059 0.656339 0.517242 11.00000 -1.50000 H1B 2 0.999874 0.918853 0.552348 11.00000 -1.50000 H1C 2 0.638123 0.891700 0.534141 11.00000 -1.50000 AFIX 0 C2 1 0.638436 0.591723 0.581481 11.00000 0.07593 0.06005 = 0.05118 -0.00082 -0.00257 0.01660 AFIX 23 H2A 2 0.422397 0.456727 0.571345 11.00000 -1.20000 H2B 2 0.782860 0.471420 0.588202 11.00000 -1.20000 AFIX 0 C11 1 -0.141859 0.715765 0.952685 11.00000 0.11347 0.11497 = 0.03438 0.02543 0.01875 0.04662 AFIX 137 H11A 2 -0.289279 0.831777 0.946611 11.00000 -1.50000 H11B 2 0.073257 0.846119 0.962889 11.00000 -1.50000 H11C 2 -0.234253 0.582636 0.975783 11.00000 -1.50000 AFIX 0 HKLF 4 REM 0003_0001_a.res in P-1 REM R1 = 0.0539 for 253 Fo > 4sig(Fo) and 0.1045 for all 586 data REM 102 parameters refined using 80 restraints END WGHT 0.1112 0.0000 REM Highest difference peak 0.072, deepest hole -0.070, 1-sigma level 0.023 Q1 1 0.0775 0.4720 0.6632 11.00000 0.05 0.07 Q2 1 0.2473 0.5102 0.6039 11.00000 0.05 0.07 Q3 1 0.0251 0.2956 0.7358 11.00000 0.05 0.06 Q4 1 0.5692 0.4770 0.4828 11.00000 0.05 0.06 Q5 1 0.3991 0.3319 0.7586 11.00000 0.05 0.06 Q6 1 0.2030 0.3091 0.8380 11.00000 0.05 0.06 ; _shelx_res_checksum 27023 _olex2_exptl_crystal_mounting_method DAC _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 1.425 _oxdiff_exptl_absorpt_empirical_full_min 0.756 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 C6 C 0.2606(8) 0.5578(7) 0.7458(2) 0.053(4) Uani 1 1 d D U . . . H6A H 0.045131 0.419585 0.736254 0.063 Uiso 1 1 calc R U . . . H6B H 0.408819 0.441190 0.752688 0.063 Uiso 1 1 calc R U . . . C4 C 0.4489(8) 0.5739(7) 0.6639(2) 0.058(4) Uani 1 1 d D U . . . H4A H 0.233964 0.435730 0.654053 0.069 Uiso 1 1 calc R U . . . H4B H 0.596829 0.456997 0.670734 0.069 Uiso 1 1 calc R U . . . C8 C 0.0760(8) 0.5453(8) 0.8278(2) 0.057(4) Uani 1 1 d D U . . . H8A H -0.140121 0.407167 0.818378 0.068 Uiso 1 1 calc R U . . . H8B H 0.224040 0.428623 0.834638 0.068 Uiso 1 1 calc R U . . . C3 C 0.5915(8) 0.7619(7) 0.6250(2) 0.055(4) Uani 1 1 d D U . . . H3A H 0.806955 0.899292 0.634783 0.066 Uiso 1 1 calc R U . . . H3B H 0.444290 0.879819 0.618296 0.066 Uiso 1 1 calc R U . . . C9 C 0.0335(8) 0.7221(7) 0.8703(3) 0.057(4) Uani 1 1 d D U . . . H9A H -0.116263 0.837285 0.863503 0.069 Uiso 1 1 calc R U . . . H9B H 0.249200 0.861696 0.879514 0.069 Uiso 1 1 calc R U . . . C10 C -0.1029(10) 0.5371(9) 0.9097(3) 0.069(4) Uani 1 1 d D U . . . H10A H 0.045510 0.420334 0.916375 0.083 Uiso 1 1 calc R U . . . H10B H -0.319781 0.399108 0.900694 0.083 Uiso 1 1 calc R U . . . C7 C 0.2156(8) 0.7317(7) 0.7886(2) 0.053(4) Uani 1 1 d D U . . . H7A H 0.067030 0.847894 0.781785 0.063 Uiso 1 1 calc R U . . . H7B H 0.431074 0.870378 0.798145 0.063 Uiso 1 1 calc R U . . . C5 C 0.4011(7) 0.7449(7) 0.7069(2) 0.054(4) Uani 1 1 d D U . . . H5A H 0.615858 0.883800 0.716653 0.065 Uiso 1 1 calc R U . . . H5B H 0.252284 0.860960 0.700097 0.065 Uiso 1 1 calc R U . . . C1 C 0.7868(11) 0.7822(8) 0.5427(3) 0.074(5) Uani 1 1 d D U . . . H1A H 0.816059 0.656339 0.517242 0.112 Uiso 1 1 calc R U . . . H1B H 0.999874 0.918853 0.552348 0.112 Uiso 1 1 calc R U . . . H1C H 0.638123 0.891700 0.534141 0.112 Uiso 1 1 calc R U . . . C2 C 0.6384(9) 0.5917(8) 0.5815(2) 0.063(4) Uani 1 1 d D U . . . H2A H 0.422397 0.456727 0.571345 0.076 Uiso 1 1 calc R U . . . H2B H 0.782860 0.471420 0.588202 0.076 Uiso 1 1 calc R U . . . C11 C -0.1419(12) 0.7158(9) 0.9527(3) 0.084(5) Uani 1 1 d D U . . . H11A H -0.289279 0.831777 0.946611 0.126 Uiso 1 1 calc R U . . . H11B H 0.073257 0.846119 0.962889 0.126 Uiso 1 1 calc R U . . . H11C H -0.234253 0.582636 0.975783 0.126 Uiso 1 1 calc R U . . . 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 C6 0.065(2) 0.0488(15) 0.042(12) -0.002(4) -0.003(4) 0.0144(13) C4 0.071(2) 0.0489(17) 0.051(13) -0.005(3) 0.000(4) 0.0151(14) C8 0.067(2) 0.0510(16) 0.049(13) 0.002(3) 0.016(4) 0.0136(13) C3 0.067(2) 0.0495(16) 0.047(13) -0.002(4) -0.001(5) 0.0155(14) C9 0.073(2) 0.0569(17) 0.040(13) 0.006(4) 0.009(5) 0.0159(15) C10 0.086(3) 0.075(2) 0.048(14) 0.009(4) 0.020(5) 0.0253(19) C7 0.066(2) 0.0485(16) 0.041(12) 0.002(3) 0.005(4) 0.0150(13) C5 0.065(2) 0.0480(16) 0.046(13) -0.003(4) 0.006(5) 0.0139(14) C1 0.091(2) 0.079(2) 0.052(15) 0.003(4) 0.017(5) 0.0231(16) C2 0.076(2) 0.0600(19) 0.051(14) -0.001(4) -0.003(5) 0.0166(15) C11 0.113(3) 0.115(3) 0.034(14) 0.025(5) 0.019(7) 0.047(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0011 0.0005 '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' loop_ _axis.id _axis.type _axis.equipment _axis.parity _axis.depends_on _axis.zero _axis.vector[1] _axis.vector[2] _axis.vector[3] source . source . . . 1.00000000 0.00000000 0.00000000 omega rotation goniometer -1 . -0.00106000 0.00000000 0.00000000 1.00000000 kappa rotation goniometer -1 omega 0.00000000 -0.76604444 0.00000000 0.64278761 phi rotation goniometer -1 kappa . 0.00000000 0.00000000 1.00000000 theta rotation goniometer -1 . 0.00200000 0.00000000 0.00000000 1.00000000 matrixX general general . phi . 1.00000000 0.00000000 0.00000000 matrixY general general . phi . 0.00000000 1.00000000 0.00000000 matrixZ general general . phi . 0.00000000 0.00000000 1.00000000 dacX translation general . phi . 0.00000000 1.00000000 0.00000000 dacY translation general . phi . -1.00000000 0.00000000 0.00000000 dacZ translation general . phi . 0.00000000 0.00000000 1.00000000 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 H6A C6 H6B 107.5 . . ? C7 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C7 C6 C5 114.8(3) . . ? C5 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? H4A C4 H4B 107.5 . . ? C3 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C5 C4 C3 115.3(3) . . ? H8A C8 H8B 107.6 . . ? C9 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C9 C8 C7 114.4(3) . . ? C7 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C4 C3 H3A 108.4 . . ? C4 C3 H3B 108.4 . . ? C4 C3 C2 115.7(3) . . ? H3A C3 H3B 107.4 . . ? C2 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? C8 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C8 C9 C10 114.6(3) . . ? H9A C9 H9B 107.6 . . ? C10 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C9 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? C9 C10 C11 114.5(4) . . ? H10A C10 H10B 107.6 . . ? C11 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C6 C7 C8 115.0(3) . . ? C6 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C6 C5 C4 115.4(3) . . ? C6 C5 H5A 108.4 . . ? C6 C5 H5B 108.4 . . ? C4 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C3 C2 C1 115.4(3) . . ? C3 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.506(5) . ? C6 C5 1.508(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C3 1.512(5) . ? C4 C5 1.508(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.505(5) . ? C8 C7 1.510(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C2 1.516(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.510(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.514(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 C2 1.519(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 C4 C3 C2 C1 -179.1(3) . . . . ? C8 C9 C10 C11 179.4(4) . . . . ? C3 C4 C5 C6 -179.7(3) . . . . ? C9 C8 C7 C6 179.8(3) . . . . ? C7 C6 C5 C4 179.8(3) . . . . ? C7 C8 C9 C10 -179.4(3) . . . . ? C5 C6 C7 C8 -179.8(3) . . . . ? C5 C4 C3 C2 -179.6(3) . . . . ?