#------------------------------------------------------------------------------ #$Date: 2026-06-02 23:11:53 +0100 (Tue, 02 Jun 2026) $ #$Revision: 306165 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577331.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_1577331 loop_ _publ_author_name 'Arvidson, Jacob' 'Shaikh, Saad' 'Tanaka, Masahiro' 'Pawale, Tejal' 'Dawson, Andrew' 'Li, Xiao' 'Nesterov, Vladimir' 'Kobori, Yasuhiro' 'Das, Somnath' 'Wang, Hong' _publ_section_title ; Linearly Acenaphthylene-Fused Pentacene Exhibiting Efficient Singlet Fission ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D5SC08246C _journal_year 2026 _chemical_formula_moiety 'C38 H22' _chemical_formula_sum 'C38 H22' _chemical_formula_weight 478.55 _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 2023-02-13 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2025-05-10 deposited with the CCDC. 2026-05-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.0277(18) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.21884(11) _cell_length_b 8.77359(18) _cell_length_c 26.1039(5) _cell_measurement_reflns_used 5787 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 80.5350 _cell_measurement_theta_min 3.3870 _cell_volume 1194.50(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _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 -38.00 -12.00 0.50 0.58 -- 0.00 85.00 -12.00 52 2 \w -14.00 11.00 0.50 0.58 -- 0.00 -85.00-131.00 50 3 \w 8.00 43.00 0.50 0.58 -- 0.00 85.00 -12.00 70 4 \w -103.00 -20.00 0.50 2.34 -- -64.25 85.00 -12.00 166 5 \w -137.00-112.00 0.50 2.34 -- -64.25 -85.00-131.00 50 6 \w 102.00 147.00 0.50 2.34 -- 64.25 85.00 -12.00 90 7 \w -118.00 -91.00 0.50 2.34 -- -103.75 85.00 -12.00 54 8 \w 146.00 172.00 0.50 2.34 -- 125.25 85.00 -12.00 52 9 \w 115.00 140.00 0.50 2.34 -- 125.25 85.00 -12.00 50 10 \w 96.00 133.00 0.50 2.34 -- 125.25 -85.00-131.00 74 11 \w -88.00 -42.00 0.50 0.58 -- 0.00 178.00 90.00 92 12 \w 2.00 27.00 0.50 0.58 -- 0.00 -99.00 -30.00 50 13 \w -103.00 -78.00 0.50 2.34 -- -64.25-125.00 30.00 50 14 \w -144.00 -91.00 0.50 2.34 -- -64.25 -77.00 150.00 106 15 \w -25.00 15.00 0.50 2.34 -- 64.25 -19.00 90.00 80 16 \w -24.00 15.00 0.50 2.34 -- 64.25 -19.00-120.00 78 17 \w -24.00 13.00 0.50 2.34 -- 64.25 -19.00 -30.00 74 18 \w -18.00 16.00 0.50 2.34 -- 64.25 -19.00 120.00 68 19 \w 20.00 45.00 0.50 2.34 -- 64.25 -85.00-131.00 50 20 \w -146.00 -87.00 0.50 2.34 -- -103.75 -37.00 -90.00 118 21 \w -152.00-127.00 0.50 2.34 -- -103.75 -85.00-131.00 50 22 \w 90.00 121.00 0.50 2.34 -- 125.25 50.00 -60.00 62 23 \w 45.00 95.00 0.50 2.34 -- 125.25 -77.00-180.00 100 24 \w 141.00 166.00 0.50 2.34 -- 125.25 50.00 -60.00 50 25 \w 116.00 168.00 0.50 2.34 -- 125.25 77.00 90.00 104 26 \w 139.00 164.00 0.50 2.34 -- 125.25 63.00 0.00 50 27 \w 88.00 145.00 0.50 2.34 -- 125.25 178.00 -90.00 114 28 \w 86.00 166.00 0.50 2.34 -- 125.25 37.00 90.00 160 29 \w 86.00 136.00 0.50 2.34 -- 125.25 37.00 0.00 100 30 \w 48.00 97.00 0.50 2.34 -- 125.25-111.00 -30.00 98 31 \w 56.00 81.00 0.50 2.34 -- 125.25 -77.00-150.00 50 32 \w 76.00 104.00 0.50 2.34 -- 125.25 -91.00 0.00 56 33 \w 97.00 178.00 0.50 2.34 -- 125.25 50.00 120.00 162 34 \w 139.00 165.00 0.50 2.34 -- 125.25 77.00-120.00 52 35 \w 46.00 71.00 0.50 2.34 -- 125.25 -86.00 89.51 50 36 \w 113.00 164.00 0.50 2.34 -- 125.25 -86.00 89.51 102 37 \w 90.00 142.00 0.50 2.34 -- 125.25 37.00-180.00 104 38 \w 63.00 89.00 0.50 2.34 -- 125.25 -77.00 -90.00 52 39 \w 45.00 70.00 0.50 2.34 -- 125.25 -77.00 30.00 50 40 \w 84.00 109.00 0.50 2.34 -- 125.25-111.00-150.00 50 41 \w 125.00 150.00 0.50 2.34 -- 125.25 37.00 120.00 50 42 \w 93.00 118.00 0.50 2.34 -- 125.25 77.00-180.00 50 43 \w 75.00 137.00 0.50 2.34 -- 125.25 178.00 90.00 124 44 \w 42.00 67.00 0.50 2.34 -- 125.25 -91.00 90.00 50 45 \w 54.00 79.00 0.50 2.34 -- 125.25-111.00 90.00 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0029260000 _diffrn_orient_matrix_UB_12 0.0489995000 _diffrn_orient_matrix_UB_13 -0.0566778000 _diffrn_orient_matrix_UB_21 0.1409716000 _diffrn_orient_matrix_UB_22 -0.1479427000 _diffrn_orient_matrix_UB_23 -0.0137961000 _diffrn_orient_matrix_UB_31 -0.2594900000 _diffrn_orient_matrix_UB_32 -0.0809298000 _diffrn_orient_matrix_UB_33 -0.0092318000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_unetI/netI 0.0260 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 8458 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 81.025 _diffrn_reflns_theta_min 3.388 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic dark bronze' _exptl_crystal_density_diffrn 1.331 _exptl_crystal_description prism _exptl_crystal_F_000 500 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.197 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2614 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0432 _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^)+(0.0438P)^2^+0.6048P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1147 _refine_ls_wR_factor_ref 0.1179 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2308 _reflns_number_total 2614 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5sc08246c2.cif _cod_data_source_block str1229lt150kcu50mm_auto _cod_database_code 1577331 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C38 H22' _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 0.989 _shelx_estimated_absorpt_t_min 0.961 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19) ; _shelx_res_file ; TITL str1229lt150kCu50mm_auto in P21/c #14 str1229lt150kcu50mm_auto.res created by SHELXL-2018/3 at 15:54:46 on 13-Feb-2023 REM reset to P21/c #14 CELL 1.54184 5.218839 8.773596 26.103929 90 92.0277 90 ZERR 2 0.000107 0.00018 0.000539 0 0.0018 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H UNIT 76 44 L.S. 10 PLAN 25 SIZE 0.02 0.03 0.07 TEMP -123.16(10) CONF BOND $H MORE -1 LIST 4 fmap 2 acta OMIT -3 2 6 OMIT 3 3 13 REM REM REM WGHT 0.043800 0.604800 FVAR 5.45583 C1 1 0.843177 -0.035276 0.455547 11.00000 0.02609 0.02369 = 0.02422 0.00039 0.00383 0.00277 C2 1 0.683530 -0.072148 0.412682 11.00000 0.02911 0.02699 = 0.02376 0.00123 0.00397 0.00259 AFIX 43 H2 2 0.708410 -0.021088 0.381152 11.00000 -1.20000 AFIX 0 C3 1 0.491374 -0.180584 0.415102 11.00000 0.02713 0.02554 = 0.02656 -0.00219 0.00283 0.00348 C4 1 0.328761 -0.218688 0.371768 11.00000 0.03277 0.03278 = 0.02748 -0.00060 0.00096 0.00064 AFIX 43 H4 2 0.350618 -0.167848 0.340089 11.00000 -1.20000 AFIX 0 C5 1 0.143514 -0.326501 0.375235 11.00000 0.03369 0.03588 = 0.03357 -0.00491 -0.00316 -0.00191 AFIX 43 H5 2 0.037024 -0.349884 0.346021 11.00000 -1.20000 AFIX 0 C6 1 0.107133 -0.404925 0.422207 11.00000 0.03305 0.03017 = 0.04028 -0.00414 0.00264 -0.00575 AFIX 43 H6 2 -0.022137 -0.480788 0.423978 11.00000 -1.20000 AFIX 0 C7 1 0.255919 -0.371966 0.464432 11.00000 0.03202 0.02834 = 0.03328 0.00070 0.00433 -0.00124 AFIX 43 H7 2 0.229067 -0.424932 0.495527 11.00000 -1.20000 AFIX 0 C8 1 0.452790 -0.258570 0.462839 11.00000 0.02707 0.02350 = 0.02914 -0.00143 0.00437 0.00240 C9 1 0.605184 -0.221112 0.505509 11.00000 0.02936 0.02491 = 0.02515 0.00176 0.00418 0.00131 AFIX 43 H9 2 0.576651 -0.271255 0.537055 11.00000 -1.20000 AFIX 0 C10 1 0.801030 -0.111093 0.503623 11.00000 0.02654 0.02302 = 0.02476 -0.00031 0.00399 0.00321 C11 1 1.042876 0.073940 0.452456 11.00000 0.02803 0.02381 = 0.02283 0.00101 0.00445 0.00310 C12 1 1.093031 0.146747 0.405006 11.00000 0.02868 0.02556 = 0.02623 -0.00048 0.00054 0.00040 C13 1 1.152222 0.210788 0.366574 11.00000 0.03220 0.02691 = 0.02675 0.00057 0.00174 0.00102 C14 1 1.237541 0.297122 0.323745 11.00000 0.02987 0.02412 = 0.02453 0.00027 0.00503 0.00293 C15 1 1.459537 0.384997 0.329195 11.00000 0.03304 0.04195 = 0.02967 0.00133 -0.00092 -0.00526 AFIX 43 H15 2 1.558096 0.382094 0.360482 11.00000 -1.20000 AFIX 0 C16 1 1.537603 0.476438 0.289419 11.00000 0.03436 0.03909 = 0.03827 0.00073 0.00562 -0.00842 AFIX 43 H16 2 1.688477 0.536385 0.293617 11.00000 -1.20000 AFIX 0 C17 1 1.396282 0.480688 0.243555 11.00000 0.04202 0.03022 = 0.03033 0.00457 0.01112 -0.00002 AFIX 43 H17 2 1.448168 0.544827 0.216495 11.00000 -1.20000 AFIX 0 C18 1 1.179633 0.391357 0.237286 11.00000 0.04302 0.03973 = 0.02549 0.00429 -0.00136 -0.00190 AFIX 43 H18 2 1.084427 0.393001 0.205592 11.00000 -1.20000 AFIX 0 C19 1 1.099811 0.299325 0.276807 11.00000 0.03442 0.03275 = 0.02860 0.00096 0.00001 -0.00578 AFIX 43 H19 2 0.951300 0.237632 0.272010 11.00000 -1.20000 AFIX 0 HKLF 4 REM str1229lt150kCu50mm_auto in P21/c #14 REM wR2 = 0.1179, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0432 for 2308 Fo > 4sig(Fo) and 0.0480 for all 2614 data REM 172 parameters refined using 0 restraints END WGHT 0.0438 0.6048 REM Highest difference peak 0.197, deepest hole -0.163, 1-sigma level 0.041 Q1 1 0.9031 0.0395 0.4562 11.00000 0.05 0.20 Q2 1 0.4715 -0.2133 0.4405 11.00000 0.05 0.19 Q3 1 1.7348 0.2433 0.3766 11.00000 0.05 0.19 Q4 1 0.8496 -0.0837 0.4775 11.00000 0.05 0.18 Q5 1 0.8929 -0.1038 0.5224 11.00000 0.05 0.17 Q6 1 0.5430 -0.1060 0.4204 11.00000 0.05 0.17 Q7 1 0.5382 -0.2399 0.4805 11.00000 0.05 0.16 Q8 1 0.7799 -0.0590 0.4335 11.00000 0.05 0.15 Q9 1 0.7630 -0.2032 0.5000 11.00000 0.05 0.14 Q10 1 0.2826 -0.2836 0.4688 11.00000 0.05 0.14 Q11 1 0.6518 -0.1334 0.5075 11.00000 0.05 0.13 Q12 1 -0.1040 -0.4409 0.4220 11.00000 0.05 0.13 Q13 1 0.4217 -0.2050 0.3929 11.00000 0.05 0.13 Q14 1 0.3976 -0.3394 0.4600 11.00000 0.05 0.13 Q15 1 0.2601 -0.4388 0.4311 11.00000 0.05 0.13 Q16 1 1.5451 0.3941 0.3035 11.00000 0.05 0.12 Q17 1 0.1766 -0.2446 0.3800 11.00000 0.05 0.12 Q18 1 1.0951 0.0971 0.4277 11.00000 0.05 0.12 Q19 1 1.5111 0.4435 0.2589 11.00000 0.05 0.12 Q20 1 0.6376 -0.1563 0.4091 11.00000 0.05 0.12 Q21 1 1.2152 0.1974 0.4006 11.00000 0.05 0.12 Q22 1 0.8676 0.2778 0.2738 11.00000 0.05 0.12 Q23 1 0.5836 -0.2744 0.4722 11.00000 0.05 0.12 Q24 1 1.5431 0.4205 0.2498 11.00000 0.05 0.11 Q25 1 0.3008 -0.3089 0.3716 11.00000 0.05 0.11 ; _shelx_res_checksum 11154 _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 1.337 _oxdiff_exptl_absorpt_empirical_full_min 0.649 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 C1 C 0.8432(2) -0.03528(15) 0.45555(5) 0.0246(3) Uani 1 1 d . . . . . C2 C 0.6835(3) -0.07215(16) 0.41268(5) 0.0265(3) Uani 1 1 d . . . . . H2 H 0.708410 -0.021088 0.381152 0.032 Uiso 1 1 calc R U . . . C3 C 0.4914(3) -0.18058(15) 0.41510(5) 0.0264(3) Uani 1 1 d . . . . . C4 C 0.3288(3) -0.21869(17) 0.37177(5) 0.0310(3) Uani 1 1 d . . . . . H4 H 0.350618 -0.167848 0.340089 0.037 Uiso 1 1 calc R U . . . C5 C 0.1435(3) -0.32650(18) 0.37523(6) 0.0345(3) Uani 1 1 d . . . . . H5 H 0.037024 -0.349884 0.346021 0.041 Uiso 1 1 calc R U . . . C6 C 0.1071(3) -0.40492(17) 0.42221(6) 0.0345(3) Uani 1 1 d . . . . . H6 H -0.022137 -0.480788 0.423978 0.041 Uiso 1 1 calc R U . . . C7 C 0.2559(3) -0.37197(17) 0.46443(6) 0.0311(3) Uani 1 1 d . . . . . H7 H 0.229067 -0.424932 0.495527 0.037 Uiso 1 1 calc R U . . . C8 C 0.4528(3) -0.25857(15) 0.46284(5) 0.0265(3) Uani 1 1 d . . . . . C9 C 0.6052(3) -0.22111(15) 0.50551(5) 0.0264(3) Uani 1 1 d . . . . . H9 H 0.576651 -0.271255 0.537055 0.032 Uiso 1 1 calc R U . . . C10 C 0.8010(2) -0.11109(15) 0.50362(5) 0.0247(3) Uani 1 1 d . . . . . C11 C 1.0429(2) 0.07394(15) 0.45246(5) 0.0248(3) Uani 1 1 d . . . . . C12 C 1.0930(3) 0.14675(16) 0.40501(5) 0.0268(3) Uani 1 1 d . . . . . C13 C 1.1522(3) 0.21079(16) 0.36657(5) 0.0286(3) Uani 1 1 d . . . . . C14 C 1.2375(3) 0.29712(15) 0.32375(5) 0.0261(3) Uani 1 1 d . . . . . C15 C 1.4595(3) 0.38500(19) 0.32920(6) 0.0349(3) Uani 1 1 d . . . . . H15 H 1.558096 0.382094 0.360482 0.042 Uiso 1 1 calc R U . . . C16 C 1.5376(3) 0.47644(19) 0.28942(6) 0.0371(4) Uani 1 1 d . . . . . H16 H 1.688477 0.536385 0.293617 0.045 Uiso 1 1 calc R U . . . C17 C 1.3963(3) 0.48069(17) 0.24356(6) 0.0340(3) Uani 1 1 d . . . . . H17 H 1.448168 0.544827 0.216495 0.041 Uiso 1 1 calc R U . . . C18 C 1.1796(3) 0.39136(19) 0.23729(6) 0.0361(3) Uani 1 1 d . . . . . H18 H 1.084427 0.393001 0.205592 0.043 Uiso 1 1 calc R U . . . C19 C 1.0998(3) 0.29933(17) 0.27681(5) 0.0319(3) Uani 1 1 d . . . . . H19 H 0.951300 0.237632 0.272010 0.038 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 C1 0.0261(6) 0.0237(6) 0.0242(6) 0.0004(5) 0.0038(5) 0.0028(5) C2 0.0291(7) 0.0270(7) 0.0238(6) 0.0012(5) 0.0040(5) 0.0026(5) C3 0.0271(6) 0.0255(6) 0.0266(6) -0.0022(5) 0.0028(5) 0.0035(5) C4 0.0328(7) 0.0328(7) 0.0275(7) -0.0006(6) 0.0010(5) 0.0006(6) C5 0.0337(7) 0.0359(8) 0.0336(7) -0.0049(6) -0.0032(6) -0.0019(6) C6 0.0331(7) 0.0302(7) 0.0403(8) -0.0041(6) 0.0026(6) -0.0058(6) C7 0.0320(7) 0.0283(7) 0.0333(7) 0.0007(6) 0.0043(6) -0.0012(6) C8 0.0271(7) 0.0235(6) 0.0291(7) -0.0014(5) 0.0044(5) 0.0024(5) C9 0.0294(7) 0.0249(6) 0.0251(6) 0.0018(5) 0.0042(5) 0.0013(5) C10 0.0265(6) 0.0230(6) 0.0248(6) -0.0003(5) 0.0040(5) 0.0032(5) C11 0.0280(6) 0.0238(6) 0.0228(6) 0.0010(5) 0.0045(5) 0.0031(5) C12 0.0287(7) 0.0256(6) 0.0262(6) -0.0005(5) 0.0005(5) 0.0004(5) C13 0.0322(7) 0.0269(7) 0.0268(6) 0.0006(5) 0.0017(5) 0.0010(5) C14 0.0299(7) 0.0241(6) 0.0245(6) 0.0003(5) 0.0050(5) 0.0029(5) C15 0.0330(7) 0.0419(8) 0.0297(7) 0.0013(6) -0.0009(6) -0.0053(6) C16 0.0344(8) 0.0391(8) 0.0383(8) 0.0007(7) 0.0056(6) -0.0084(6) C17 0.0420(8) 0.0302(7) 0.0303(7) 0.0046(6) 0.0111(6) 0.0000(6) C18 0.0430(8) 0.0397(8) 0.0255(7) 0.0043(6) -0.0014(6) -0.0019(7) C19 0.0344(7) 0.0328(7) 0.0286(7) 0.0010(6) 0.0000(6) -0.0058(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' 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 C1 C10 118.72(12) . . ? C2 C1 C11 121.63(12) . . ? C11 C1 C10 119.66(12) . . ? C1 C2 H2 119.0 . . ? C3 C2 C1 122.02(12) . . ? C3 C2 H2 119.0 . . ? C2 C3 C4 122.34(13) . . ? C2 C3 C8 119.26(12) . . ? C4 C3 C8 118.41(12) . . ? C3 C4 H4 119.5 . . ? C5 C4 C3 120.95(13) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 119.6 . . ? C4 C5 C6 120.71(14) . . ? C6 C5 H5 119.6 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.43(14) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 119.5 . . ? C6 C7 C8 121.01(14) . . ? C8 C7 H7 119.5 . . ? C7 C8 C3 118.49(13) . . ? C9 C8 C3 119.25(12) . . ? C9 C8 C7 122.26(13) . . ? C8 C9 H9 118.9 . . ? C8 C9 C10 122.10(12) . . ? C10 C9 H9 118.9 . . ? C9 C10 C1 118.64(12) . . ? C9 C10 C11 121.69(12) . 3_756 ? C11 C10 C1 119.67(12) 3_756 . ? C1 C11 C10 120.66(12) . 3_756 ? C1 C11 C12 120.61(12) . . ? C10 C11 C12 118.72(12) 3_756 . ? C13 C12 C11 175.29(15) . . ? C12 C13 C14 174.45(15) . . ? C15 C14 C13 119.48(12) . . ? C15 C14 C19 118.75(13) . . ? C19 C14 C13 121.74(13) . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.61(13) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.15(14) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 120.1 . . ? C18 C17 C16 119.75(13) . . ? C18 C17 H17 120.1 . . ? C17 C18 H18 119.7 . . ? C17 C18 C19 120.60(14) . . ? C19 C18 H18 119.7 . . ? C14 C19 H19 119.9 . . ? C18 C19 C14 120.10(13) . . ? C18 C19 H19 119.9 . . ? 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 C1 C2 1.4089(18) . ? C1 C10 1.4441(18) . ? C1 C11 1.4201(18) . ? C2 H2 0.9500 . ? C2 C3 1.3854(19) . ? C3 C4 1.4295(19) . ? C3 C8 1.4420(19) . ? C4 H4 0.9500 . ? C4 C5 1.358(2) . ? C5 H5 0.9500 . ? C5 C6 1.425(2) . ? C6 H6 0.9500 . ? C6 C7 1.357(2) . ? C7 H7 0.9500 . ? C7 C8 1.4318(19) . ? C8 C9 1.3851(19) . ? C9 H9 0.9500 . ? C9 C10 1.4080(19) . ? C10 C11 1.4207(18) 3_756 ? C11 C12 1.4261(18) . ? C12 C13 1.200(2) . ? C13 C14 1.4343(18) . ? C14 C15 1.395(2) . ? C14 C19 1.3986(19) . ? C15 H15 0.9500 . ? C15 C16 1.385(2) . ? C16 H16 0.9500 . ? C16 C17 1.384(2) . ? C17 H17 0.9500 . ? C17 C18 1.381(2) . ? C18 H18 0.9500 . ? C18 C19 1.386(2) . ? C19 H19 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 C1 C2 C3 C4 -179.95(13) . . . . ? C1 C2 C3 C8 0.0(2) . . . . ? C2 C1 C10 C9 1.23(18) . . . . ? C2 C1 C10 C11 -179.02(12) . . . 3_756 ? C2 C1 C11 C10 179.00(12) . . . 3_756 ? C2 C1 C11 C12 -1.94(19) . . . . ? C2 C3 C4 C5 179.41(14) . . . . ? C2 C3 C8 C7 -179.05(12) . . . . ? C2 C3 C8 C9 1.33(19) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C3 C8 C9 C10 -1.3(2) . . . . ? C4 C3 C8 C7 0.86(19) . . . . ? C4 C3 C8 C9 -178.76(12) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C3 -0.5(2) . . . . ? C6 C7 C8 C9 179.10(14) . . . . ? C7 C8 C9 C10 179.07(13) . . . . ? C8 C3 C4 C5 -0.5(2) . . . . ? C8 C9 C10 C1 0.0(2) . . . . ? C8 C9 C10 C11 -179.71(12) . . . 3_756 ? C10 C1 C2 C3 -1.2(2) . . . . ? C10 C1 C11 C10 -1.0(2) . . . 3_756 ? C10 C1 C11 C12 178.06(12) . . . . ? C11 C1 C2 C3 178.77(12) . . . . ? C11 C1 C10 C9 -178.77(12) . . . . ? C11 C1 C10 C11 1.0(2) . . . 3_756 ? C13 C14 C15 C16 -176.13(14) . . . . ? C13 C14 C19 C18 176.04(14) . . . . ? C14 C15 C16 C17 -0.4(2) . . . . ? C15 C14 C19 C18 -2.1(2) . . . . ? C15 C16 C17 C18 -1.1(2) . . . . ? C16 C17 C18 C19 1.1(2) . . . . ? C17 C18 C19 C14 0.5(2) . . . . ? C19 C14 C15 C16 2.0(2) . . . . ?