#------------------------------------------------------------------------------ #$Date: 2024-07-09 01:21:09 +0300 (Tue, 09 Jul 2024) $ #$Revision: 293308 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572106.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_1572106 loop_ _publ_author_name 'Jenek, Niko A.' 'Helbig, Andreas' 'Boyt, Stuart M.' 'Kaur, M.' 'Sanderson, Hugh J.' 'Reeksting, Shaun Bernard' 'Kociok-K\"ohn, Gabriele' 'Helten, Holger' 'Hintermair, Ulrich' _publ_section_title ; Understanding and tuning the electronic structure of pentalenides ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D3SC04622B _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C27 H22' _chemical_formula_sum 'C27 H22' _chemical_formula_weight 346.44 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-07-12 deposited with the CCDC. 2024-07-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.095(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.0055(2) _cell_length_b 8.75137(16) _cell_length_c 12.0243(3) _cell_measurement_reflns_used 8814 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 72.2210 _cell_measurement_theta_min 4.9460 _cell_volume 940.38(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.1150 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _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 0.0377 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 18689 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.817 _diffrn_reflns_theta_min 3.704 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.519 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.224 _exptl_crystal_description block _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.199 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 1467 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.416 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 3691 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.416 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0375 _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^)+(0.0240P)^2^+0.2701P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1101 _refine_ls_wR_factor_ref 0.1109 _reflns_Friedel_coverage 0.846 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.967 _reflns_number_gt 3470 _reflns_number_total 3691 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3sc04622b2.cif _cod_data_source_block s22uh8 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1572106 _shelx_shelxl_version_number 2018/3 _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_min 0.936 _shelx_estimated_absorpt_t_max 0.974 _oxdiff_exptl_absorpt_empirical_full_min 0.688 _oxdiff_exptl_absorpt_empirical_full_max 1.206 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL shelxt_a.res in P2(1) s22uh8.res created by SHELXL-2018/3 at 15:36:42 on 19-Aug-2022 CELL 1.54184 9.0055 8.75137 12.0243 90.000 97.095 90.000 ZERR 2.00 0.0002 0.00016 0.0003 0.000 0.002 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H UNIT 54 44 ACTA FMAP 2 PLAN 5 BOND $H CONF LIST 4 L.S. 10 TEMP -123.00 SIZE 0.05 0.09 0.13 WGHT 0.024000 0.270100 FVAR 8.51984 C1 1 0.499848 0.431590 0.642195 11.00000 0.03758 0.06549 = 0.03586 -0.00430 0.01089 -0.00264 AFIX 137 H1A 2 0.595342 0.438968 0.690736 11.00000 -1.50000 H1B 2 0.424555 0.385412 0.684031 11.00000 -1.50000 H1C 2 0.466921 0.533998 0.617047 11.00000 -1.50000 AFIX 0 C2 1 0.519638 0.332685 0.540766 11.00000 0.03407 0.03693 = 0.03314 0.00461 0.00715 -0.00255 AFIX 13 H2 2 0.549374 0.227076 0.566323 11.00000 -1.20000 AFIX 0 C3 1 0.373953 0.325148 0.457366 11.00000 0.03732 0.04123 = 0.03471 0.00283 0.00789 -0.00380 AFIX 23 H3A 2 0.338824 0.218169 0.448197 11.00000 -1.20000 H3B 2 0.294315 0.386628 0.485684 11.00000 -1.20000 AFIX 0 C4 1 0.408961 0.387600 0.347343 11.00000 0.03327 0.02752 = 0.03321 -0.00133 0.00842 -0.00315 C5 1 0.290632 0.419849 0.255246 11.00000 0.02813 0.03458 = 0.03105 -0.00256 0.00693 0.00181 C6 1 0.160104 0.332577 0.241357 11.00000 0.03403 0.04497 = 0.03750 -0.00040 0.00869 -0.00274 AFIX 43 H6 2 0.148982 0.249810 0.290777 11.00000 -1.20000 AFIX 0 C7 1 0.046575 0.365368 0.156260 11.00000 0.02901 0.05677 = 0.04424 -0.00570 0.00490 -0.00118 AFIX 43 H7 2 -0.041561 0.304676 0.147594 11.00000 -1.20000 AFIX 0 C8 1 0.060380 0.485444 0.083949 11.00000 0.03643 0.05631 = 0.04031 -0.00521 0.00019 0.01465 AFIX 43 H8 2 -0.017157 0.506386 0.024920 11.00000 -1.20000 AFIX 0 C9 1 0.187927 0.575323 0.097880 11.00000 0.04093 0.04028 = 0.03979 0.00163 0.00415 0.01052 AFIX 43 H9 2 0.197192 0.659342 0.049185 11.00000 -1.20000 AFIX 0 C10 1 0.301689 0.542874 0.182543 11.00000 0.02943 0.03566 = 0.03887 -0.00154 0.00596 0.00204 AFIX 43 H10 2 0.388774 0.605119 0.191495 11.00000 -1.20000 AFIX 0 C11 1 0.559417 0.417566 0.354461 11.00000 0.02742 0.02680 = 0.03093 -0.00053 0.00450 0.00038 C12 1 0.671003 0.479522 0.288640 11.00000 0.03102 0.02752 = 0.03057 -0.00134 0.00872 -0.00037 C13 1 0.659127 0.507863 0.166910 11.00000 0.02163 0.03368 = 0.02954 -0.00058 0.00296 0.00243 C14 1 0.602961 0.398261 0.089546 11.00000 0.04222 0.03377 = 0.03674 -0.00323 0.00661 -0.00443 AFIX 43 H14 2 0.567359 0.303725 0.114678 11.00000 -1.20000 AFIX 0 C15 1 0.598583 0.426328 -0.024845 11.00000 0.04469 0.04551 = 0.03298 -0.00839 0.00147 -0.00014 AFIX 43 H15 2 0.560194 0.350551 -0.077248 11.00000 -1.20000 AFIX 0 C16 1 0.649238 0.562502 -0.062548 11.00000 0.04064 0.05086 = 0.02812 0.00317 0.00566 0.00393 AFIX 43 H16 2 0.646335 0.580690 -0.140676 11.00000 -1.20000 AFIX 0 C17 1 0.704459 0.672971 0.013657 11.00000 0.03971 0.04083 = 0.03613 0.00618 0.00744 -0.00152 AFIX 43 H17 2 0.739393 0.767537 -0.011939 11.00000 -1.20000 AFIX 0 C18 1 0.708771 0.645491 0.127578 11.00000 0.03113 0.03590 = 0.03343 -0.00139 0.00529 -0.00429 AFIX 43 H18 2 0.746319 0.722119 0.179559 11.00000 -1.20000 AFIX 0 C19 1 0.797690 0.499049 0.362155 11.00000 0.02766 0.03347 = 0.03116 -0.00075 0.00603 0.00038 AFIX 43 H19 2 0.888382 0.541160 0.342986 11.00000 -1.20000 AFIX 0 C20 1 0.775088 0.446053 0.475401 11.00000 0.03069 0.02764 = 0.02988 -0.00043 0.00601 0.00285 C21 1 0.891347 0.458794 0.572135 11.00000 0.03108 0.02880 = 0.03117 -0.00177 0.00699 0.00507 C22 1 1.008951 0.563570 0.571737 11.00000 0.03390 0.03319 = 0.03379 0.00155 0.00611 0.00373 AFIX 43 H22 2 1.015985 0.623218 0.506584 11.00000 -1.20000 AFIX 0 C23 1 1.114719 0.581875 0.664018 11.00000 0.02676 0.03678 = 0.04344 -0.00162 0.00046 0.00097 AFIX 43 H23 2 1.193622 0.653467 0.661917 11.00000 -1.20000 AFIX 0 C24 1 1.105997 0.496192 0.759474 11.00000 0.03486 0.04273 = 0.03964 0.00036 -0.00509 0.00578 AFIX 43 H24 2 1.177822 0.509654 0.823533 11.00000 -1.20000 AFIX 0 C25 1 0.991997 0.390698 0.761134 11.00000 0.04069 0.04566 = 0.03706 0.00956 0.00016 0.00721 AFIX 43 H25 2 0.985918 0.331487 0.826636 11.00000 -1.20000 AFIX 0 C26 1 0.887082 0.370599 0.668680 11.00000 0.03106 0.03532 = 0.03877 0.00471 0.00294 0.00057 AFIX 43 H26 2 0.810905 0.295884 0.670566 11.00000 -1.20000 AFIX 0 C27 1 0.632144 0.394141 0.468075 11.00000 0.03037 0.02720 = 0.02849 0.00022 0.00554 0.00149 HKLF 4 REM shelxt_a.res in P2(1) REM wR2 = 0.1109, GooF = S = 1.416, Restrained GooF = 1.416 for all data REM R1 = 0.0375 for 3470 Fo > 4sig(Fo) and 0.0417 for all 3691 data REM 245 parameters refined using 1 restraints END WGHT 0.0243 0.2690 REM Highest difference peak 0.199, deepest hole -0.239, 1-sigma level 0.041 Q1 1 1.0202 0.5935 0.6347 11.00000 0.05 0.20 Q2 1 0.8479 0.4354 0.5188 11.00000 0.05 0.20 Q3 1 0.5958 0.4928 0.3111 11.00000 0.05 0.18 Q4 1 0.4789 0.4424 0.3425 11.00000 0.05 0.18 Q5 1 0.7779 0.4907 0.4241 11.00000 0.05 0.17 ; _shelx_res_checksum 78598 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 C1 C 0.4998(4) 0.4316(5) 0.6422(3) 0.0458(10) Uani 1 1 d . . . . . H1A H 0.595342 0.438968 0.690736 0.069 Uiso 1 1 calc R U . . . H1B H 0.424555 0.385412 0.684031 0.069 Uiso 1 1 calc R U . . . H1C H 0.466921 0.533998 0.617047 0.069 Uiso 1 1 calc R U . . . C2 C 0.5196(4) 0.3327(4) 0.5408(3) 0.0345(8) Uani 1 1 d . . . . . H2 H 0.549374 0.227076 0.566323 0.041 Uiso 1 1 calc R U . . . C3 C 0.3740(4) 0.3251(4) 0.4574(3) 0.0375(8) Uani 1 1 d . . . . . H3A H 0.338824 0.218169 0.448197 0.045 Uiso 1 1 calc R U . . . H3B H 0.294315 0.386628 0.485684 0.045 Uiso 1 1 calc R U . . . C4 C 0.4090(4) 0.3876(4) 0.3473(3) 0.0310(7) Uani 1 1 d . . . . . C5 C 0.2906(4) 0.4198(4) 0.2552(3) 0.0310(7) Uani 1 1 d . . . . . C6 C 0.1601(4) 0.3326(4) 0.2414(3) 0.0385(8) Uani 1 1 d . . . . . H6 H 0.148982 0.249810 0.290777 0.046 Uiso 1 1 calc R U . . . C7 C 0.0466(4) 0.3654(5) 0.1563(3) 0.0433(9) Uani 1 1 d . . . . . H7 H -0.041561 0.304676 0.147594 0.052 Uiso 1 1 calc R U . . . C8 C 0.0604(4) 0.4854(5) 0.0839(3) 0.0447(9) Uani 1 1 d . . . . . H8 H -0.017157 0.506386 0.024920 0.054 Uiso 1 1 calc R U . . . C9 C 0.1879(4) 0.5753(5) 0.0979(3) 0.0404(8) Uani 1 1 d . . . . . H9 H 0.197192 0.659342 0.049185 0.048 Uiso 1 1 calc R U . . . C10 C 0.3017(4) 0.5429(4) 0.1825(3) 0.0345(8) Uani 1 1 d . . . . . H10 H 0.388774 0.605119 0.191495 0.041 Uiso 1 1 calc R U . . . C11 C 0.5594(4) 0.4176(4) 0.3545(3) 0.0283(7) Uani 1 1 d . . . . . C12 C 0.6710(4) 0.4795(4) 0.2886(3) 0.0293(7) Uani 1 1 d . . . . . C13 C 0.6591(4) 0.5079(4) 0.1669(3) 0.0283(7) Uani 1 1 d . . . . . C14 C 0.6030(4) 0.3983(4) 0.0895(3) 0.0374(8) Uani 1 1 d . . . . . H14 H 0.567359 0.303725 0.114678 0.045 Uiso 1 1 calc R U . . . C15 C 0.5986(4) 0.4263(5) -0.0248(3) 0.0413(9) Uani 1 1 d . . . . . H15 H 0.560194 0.350551 -0.077248 0.050 Uiso 1 1 calc R U . . . C16 C 0.6492(4) 0.5625(5) -0.0625(3) 0.0398(8) Uani 1 1 d . . . . . H16 H 0.646335 0.580690 -0.140676 0.048 Uiso 1 1 calc R U . . . C17 C 0.7045(4) 0.6730(4) 0.0137(3) 0.0387(8) Uani 1 1 d . . . . . H17 H 0.739393 0.767537 -0.011939 0.046 Uiso 1 1 calc R U . . . C18 C 0.7088(4) 0.6455(4) 0.1276(3) 0.0334(8) Uani 1 1 d . . . . . H18 H 0.746319 0.722119 0.179559 0.040 Uiso 1 1 calc R U . . . C19 C 0.7977(4) 0.4990(4) 0.3622(3) 0.0306(7) Uani 1 1 d . . . . . H19 H 0.888382 0.541160 0.342986 0.037 Uiso 1 1 calc R U . . . C20 C 0.7751(4) 0.4461(4) 0.4754(3) 0.0292(7) Uani 1 1 d . . . . . C21 C 0.8913(4) 0.4588(4) 0.5721(3) 0.0301(7) Uani 1 1 d . . . . . C22 C 1.0090(4) 0.5636(4) 0.5717(3) 0.0335(8) Uani 1 1 d . . . . . H22 H 1.015985 0.623218 0.506584 0.040 Uiso 1 1 calc R U . . . C23 C 1.1147(4) 0.5819(4) 0.6640(3) 0.0360(8) Uani 1 1 d . . . . . H23 H 1.193622 0.653467 0.661917 0.043 Uiso 1 1 calc R U . . . C24 C 1.1060(4) 0.4962(5) 0.7595(3) 0.0399(8) Uani 1 1 d . . . . . H24 H 1.177822 0.509654 0.823533 0.048 Uiso 1 1 calc R U . . . C25 C 0.9920(4) 0.3907(5) 0.7611(3) 0.0415(8) Uani 1 1 d . . . . . H25 H 0.985918 0.331487 0.826636 0.050 Uiso 1 1 calc R U . . . C26 C 0.8871(4) 0.3706(4) 0.6687(3) 0.0352(8) Uani 1 1 d . . . . . H26 H 0.810905 0.295884 0.670566 0.042 Uiso 1 1 calc R U . . . C27 C 0.6321(4) 0.3941(4) 0.4681(3) 0.0285(7) 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 C1 0.038(2) 0.065(3) 0.0359(19) -0.0043(18) 0.0109(16) -0.0026(19) C2 0.0341(19) 0.0369(18) 0.0331(17) 0.0046(15) 0.0071(15) -0.0026(15) C3 0.037(2) 0.0412(19) 0.0347(19) 0.0028(16) 0.0079(16) -0.0038(16) C4 0.0333(18) 0.0275(16) 0.0332(16) -0.0013(13) 0.0084(14) -0.0032(14) C5 0.0281(17) 0.0346(18) 0.0311(16) -0.0026(14) 0.0069(13) 0.0018(14) C6 0.034(2) 0.045(2) 0.0375(19) -0.0004(16) 0.0087(16) -0.0027(16) C7 0.0290(19) 0.057(3) 0.044(2) -0.0057(18) 0.0049(16) -0.0012(17) C8 0.036(2) 0.056(2) 0.040(2) -0.0052(18) 0.0002(16) 0.0146(19) C9 0.041(2) 0.0403(19) 0.0398(19) 0.0016(16) 0.0041(16) 0.0105(16) C10 0.0294(18) 0.0357(19) 0.0389(18) -0.0015(14) 0.0060(15) 0.0020(14) C11 0.0274(16) 0.0268(15) 0.0309(15) -0.0005(13) 0.0045(13) 0.0004(13) C12 0.0310(18) 0.0275(15) 0.0306(16) -0.0013(13) 0.0087(14) -0.0004(14) C13 0.0216(16) 0.0337(16) 0.0295(16) -0.0006(13) 0.0030(12) 0.0024(13) C14 0.042(2) 0.0338(18) 0.0367(18) -0.0032(15) 0.0066(15) -0.0044(16) C15 0.045(2) 0.046(2) 0.0330(18) -0.0084(16) 0.0015(16) -0.0001(18) C16 0.041(2) 0.051(2) 0.0281(17) 0.0032(16) 0.0057(15) 0.0039(17) C17 0.040(2) 0.041(2) 0.0361(19) 0.0062(15) 0.0074(16) -0.0015(16) C18 0.031(2) 0.0359(18) 0.0334(18) -0.0014(15) 0.0053(15) -0.0043(14) C19 0.0277(18) 0.0335(17) 0.0312(16) -0.0007(14) 0.0060(13) 0.0004(14) C20 0.0307(18) 0.0276(15) 0.0299(16) -0.0004(12) 0.0060(13) 0.0029(13) C21 0.0311(19) 0.0288(16) 0.0312(16) -0.0018(13) 0.0070(14) 0.0051(13) C22 0.0339(19) 0.0332(17) 0.0338(17) 0.0015(14) 0.0061(15) 0.0037(15) C23 0.0268(18) 0.0368(18) 0.0434(19) -0.0016(16) 0.0005(15) 0.0010(15) C24 0.035(2) 0.0427(19) 0.0396(19) 0.0004(16) -0.0051(15) 0.0058(17) C25 0.041(2) 0.046(2) 0.0371(19) 0.0096(17) 0.0002(16) 0.0072(17) C26 0.0311(18) 0.0353(18) 0.0388(19) 0.0047(14) 0.0029(15) 0.0006(14) C27 0.0304(17) 0.0272(15) 0.0285(15) 0.0002(13) 0.0055(13) 0.0015(13) 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C27 C2 C1 114.4(3) . . ? C27 C2 C3 102.4(3) . . ? C1 C2 C3 111.6(3) . . ? C27 C2 H2 109.4 . . ? C1 C2 H2 109.4 . . ? C3 C2 H2 109.4 . . ? C4 C3 C2 107.5(3) . . ? C4 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C11 C4 C5 129.1(3) . . ? C11 C4 C3 109.1(3) . . ? C5 C4 C3 121.6(3) . . ? C6 C5 C10 118.1(3) . . ? C6 C5 C4 120.5(3) . . ? C10 C5 C4 121.3(3) . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 121.0(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C4 C11 C27 111.0(3) . . ? C4 C11 C12 141.1(3) . . ? C27 C11 C12 107.6(3) . . ? C19 C12 C11 105.8(3) . . ? C19 C12 C13 125.0(3) . . ? C11 C12 C13 129.1(3) . . ? C14 C13 C18 118.5(3) . . ? C14 C13 C12 121.6(3) . . ? C18 C13 C12 119.8(3) . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 119.7(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 121.1(3) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C12 C19 C20 111.0(3) . . ? C12 C19 H19 124.5 . . ? C20 C19 H19 124.5 . . ? C27 C20 C21 130.8(3) . . ? C27 C20 C19 106.4(3) . . ? C21 C20 C19 122.7(3) . . ? C26 C21 C22 117.5(3) . . ? C26 C21 C20 121.7(3) . . ? C22 C21 C20 120.8(3) . . ? C23 C22 C21 121.4(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.1(3) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 120.8(3) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C20 C27 C11 109.1(3) . . ? C20 C27 C2 141.0(3) . . ? C11 C27 C2 109.6(3) . . ? 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 1.524(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C27 1.516(4) . ? C2 C3 1.551(5) . ? C2 H2 1.0000 . ? C3 C4 1.500(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C11 1.372(5) . ? C4 C5 1.466(5) . ? C5 C6 1.394(5) . ? C5 C10 1.398(5) . ? C6 C7 1.384(5) . ? C6 H6 0.9500 . ? C7 C8 1.379(6) . ? C7 H7 0.9500 . ? C8 C9 1.385(6) . ? C8 H8 0.9500 . ? C9 C10 1.382(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C27 1.455(4) . ? C11 C12 1.458(4) . ? C12 C19 1.365(5) . ? C12 C13 1.475(4) . ? C13 C14 1.387(5) . ? C13 C18 1.388(5) . ? C14 C15 1.393(5) . ? C14 H14 0.9500 . ? C15 C16 1.373(6) . ? C15 H15 0.9500 . ? C16 C17 1.382(5) . ? C16 H16 0.9500 . ? C17 C18 1.387(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.476(4) . ? C19 H19 0.9500 . ? C20 C27 1.358(5) . ? C20 C21 1.470(5) . ? C21 C26 1.399(5) . ? C21 C22 1.401(5) . ? C22 C23 1.380(5) . ? C22 H22 0.9500 . ? C23 C24 1.381(5) . ? C23 H23 0.9500 . ? C24 C25 1.383(6) . ? C24 H24 0.9500 . ? C25 C26 1.378(5) . ? C25 H25 0.9500 . ? C26 H26 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 C27 C2 C3 C4 -2.6(4) . . . . ? C1 C2 C3 C4 120.2(3) . . . . ? C2 C3 C4 C11 5.2(4) . . . . ? C2 C3 C4 C5 -170.0(3) . . . . ? C11 C4 C5 C6 154.4(3) . . . . ? C3 C4 C5 C6 -31.4(5) . . . . ? C11 C4 C5 C10 -28.8(5) . . . . ? C3 C4 C5 C10 145.3(3) . . . . ? C10 C5 C6 C7 1.4(5) . . . . ? C4 C5 C6 C7 178.3(3) . . . . ? C5 C6 C7 C8 -0.3(6) . . . . ? C6 C7 C8 C9 -1.1(6) . . . . ? C7 C8 C9 C10 1.2(6) . . . . ? C8 C9 C10 C5 0.0(5) . . . . ? C6 C5 C10 C9 -1.3(5) . . . . ? C4 C5 C10 C9 -178.1(3) . . . . ? C5 C4 C11 C27 169.0(3) . . . . ? C3 C4 C11 C27 -5.8(4) . . . . ? C5 C4 C11 C12 -3.0(7) . . . . ? C3 C4 C11 C12 -177.8(4) . . . . ? C4 C11 C12 C19 168.7(4) . . . . ? C27 C11 C12 C19 -3.4(4) . . . . ? C4 C11 C12 C13 -15.0(7) . . . . ? C27 C11 C12 C13 172.9(3) . . . . ? C19 C12 C13 C14 127.7(4) . . . . ? C11 C12 C13 C14 -47.9(5) . . . . ? C19 C12 C13 C18 -50.5(5) . . . . ? C11 C12 C13 C18 133.9(4) . . . . ? C18 C13 C14 C15 0.7(5) . . . . ? C12 C13 C14 C15 -177.5(3) . . . . ? C13 C14 C15 C16 -0.2(6) . . . . ? C14 C15 C16 C17 -0.3(6) . . . . ? C15 C16 C17 C18 0.2(6) . . . . ? C16 C17 C18 C13 0.4(6) . . . . ? C14 C13 C18 C17 -0.8(5) . . . . ? C12 C13 C18 C17 177.4(3) . . . . ? C11 C12 C19 C20 2.1(4) . . . . ? C13 C12 C19 C20 -174.4(3) . . . . ? C12 C19 C20 C27 0.1(4) . . . . ? C12 C19 C20 C21 -177.7(3) . . . . ? C27 C20 C21 C26 22.0(5) . . . . ? C19 C20 C21 C26 -160.8(3) . . . . ? C27 C20 C21 C22 -156.3(3) . . . . ? C19 C20 C21 C22 20.9(5) . . . . ? C26 C21 C22 C23 -1.5(5) . . . . ? C20 C21 C22 C23 176.8(3) . . . . ? C21 C22 C23 C24 -0.1(5) . . . . ? C22 C23 C24 C25 0.9(5) . . . . ? C23 C24 C25 C26 -0.1(6) . . . . ? C24 C25 C26 C21 -1.5(6) . . . . ? C22 C21 C26 C25 2.3(5) . . . . ? C20 C21 C26 C25 -176.0(3) . . . . ? C21 C20 C27 C11 175.2(3) . . . . ? C19 C20 C27 C11 -2.3(4) . . . . ? C21 C20 C27 C2 2.4(7) . . . . ? C19 C20 C27 C2 -175.1(4) . . . . ? C4 C11 C27 C20 -171.1(3) . . . . ? C12 C11 C27 C20 3.6(4) . . . . ? C4 C11 C27 C2 4.1(4) . . . . ? C12 C11 C27 C2 178.8(3) . . . . ? C1 C2 C27 C20 51.3(6) . . . . ? C3 C2 C27 C20 172.1(4) . . . . ? C1 C2 C27 C11 -121.6(3) . . . . ? C3 C2 C27 C11 -0.7(4) . . . . ?