#------------------------------------------------------------------------------ #$Date: 2020-04-28 01:09:58 +0300 (Tue, 28 Apr 2020) $ #$Revision: 251196 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557927.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_1557927 loop_ _publ_author_name 'Curbet, Idriss' 'Colombel-Rouen, Sophie' 'Manguin, Romane' 'Clermont, Anthony' 'Quelhas, Alexandre' 'M\"uller, Daniel S.' 'Roisnel, Thierry' 'Basle, Olivier' 'Trolez, Yann' 'Mauduit, Marc' _publ_section_title ; Expedient Synthesis of Conjugated Triynes via Alkyne Metathesis ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01124J _journal_year 2020 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C14 H14' _chemical_formula_sum 'C14 H14' _chemical_formula_weight 182.25 _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 _audit_update_record ; 2019-04-04 deposited with the CCDC. 2020-04-27 downloaded from the CCDC. ; _cell_angle_alpha 90.902(5) _cell_angle_beta 91.564(5) _cell_angle_gamma 91.339(4) _cell_formula_units_Z 4 _cell_length_a 7.5855(9) _cell_length_b 8.3989(11) _cell_length_c 17.377(2) _cell_measurement_reflns_used 9806 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5963 _cell_measurement_theta_min 2.4260 _cell_measurement_wavelength 0.71073 _cell_volume 1106.2(2) _computing_cell_refinement 'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)' _computing_data_collection 'SAINT (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2018)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_detector '(CMOS) PHOTON 100' _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 21175 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.480 _diffrn_reflns_theta_min 3.347 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.094 _exptl_crystal_description prism _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.490 _exptl_crystal_size_mid 0.410 _exptl_crystal_size_min 0.270 _refine_diff_density_max 0.307 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 4978 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0506 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.4906P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1353 _refine_ls_wR_factor_ref 0.1420 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4166 _reflns_number_total 4978 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d0sc01124j2.cif _cod_data_source_block ANC42 _cod_database_code 1557927 _shelx_res_file ; TITL import_a.res in P-1 job.res created by SHELXL-2018/3 at 12:25:13 on 22-May-2018 CELL 0.71073 7.5855 8.3989 17.3773 90.902 91.564 91.339 ZERR 4.00 0.0009 0.0011 0.0022 0.005 0.005 0.004 LATT 1 SFAC C H UNIT 56 56 MERG 2 FMAP 2 PLAN 20 ACTA HTAB 2.00000 BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.065700 0.490600 FVAR 1.10924 MOLE 1 C1 1 0.871647 0.590574 0.357388 11.00000 0.01817 0.02503 = 0.02484 0.00321 0.00070 0.00153 C2 1 0.874098 0.751982 0.381231 11.00000 0.01987 0.02628 = 0.02708 0.00150 0.00153 0.00358 C3 1 0.927053 0.866476 0.329422 11.00000 0.02557 0.02313 = 0.03192 0.00128 0.00116 0.00198 AFIX 43 H3 2 0.927045 0.975573 0.344707 11.00000 -1.20000 AFIX 0 C4 1 0.980254 0.826203 0.255630 11.00000 0.01998 0.03038 = 0.02830 0.00577 0.00026 -0.00135 C5 1 0.977386 0.666695 0.233623 11.00000 0.02373 0.03421 = 0.02407 -0.00048 0.00283 -0.00126 AFIX 43 H5 2 1.014007 0.638292 0.183500 11.00000 -1.20000 AFIX 0 C6 1 0.922491 0.546748 0.282699 11.00000 0.02005 0.02773 = 0.02890 -0.00131 0.00162 0.00013 C7 1 0.821405 0.797957 0.461320 11.00000 0.03427 0.03378 = 0.02982 -0.00163 0.00656 0.00583 AFIX 137 H7A 2 0.831728 0.913901 0.468037 11.00000 -1.50000 H7B 2 0.899107 0.746898 0.499035 11.00000 -1.50000 H7C 2 0.699080 0.763000 0.469025 11.00000 -1.50000 AFIX 0 C8 1 1.040758 0.952753 0.201060 11.00000 0.03332 0.03739 = 0.03585 0.01145 0.00313 -0.00447 AFIX 137 H8A 2 0.953851 1.037189 0.198769 11.00000 -1.50000 H8B 2 1.052814 0.905481 0.149608 11.00000 -1.50000 H8C 2 1.154945 0.997861 0.219327 11.00000 -1.50000 AFIX 0 C9 1 0.919912 0.374925 0.256743 11.00000 0.03857 0.03072 = 0.04102 -0.00869 0.00925 -0.00510 AFIX 137 H9A 2 0.922381 0.368927 0.200418 11.00000 -1.50000 H9B 2 0.812324 0.321562 0.274266 11.00000 -1.50000 H9C 2 1.023352 0.322380 0.278641 11.00000 -1.50000 AFIX 0 C10 1 0.817210 0.470384 0.409873 11.00000 0.02227 0.02577 = 0.02849 0.00161 0.00022 0.00239 C11 1 0.768999 0.370669 0.454523 11.00000 0.02509 0.02540 = 0.02812 0.00118 0.00101 0.00207 C12 1 0.713257 0.258891 0.505944 11.00000 0.02799 0.02431 = 0.02598 -0.00102 0.00160 0.00120 C13 1 0.665511 0.163695 0.552443 11.00000 0.03236 0.02579 = 0.02580 -0.00107 0.00187 -0.00105 C14 1 0.609610 0.048135 0.609694 11.00000 0.04417 0.03737 = 0.02741 0.00516 0.00527 -0.00594 AFIX 137 H14A 2 0.713713 -0.000300 0.633335 11.00000 -1.50000 H14B 2 0.534585 -0.034962 0.584532 11.00000 -1.50000 H14C 2 0.543133 0.102354 0.649517 11.00000 -1.50000 AFIX 0 MOLE 2 C21 1 0.375299 1.087195 0.892846 11.00000 0.01917 0.02114 = 0.02035 -0.00057 -0.00099 -0.00037 C22 1 0.290567 1.033417 0.959321 11.00000 0.01993 0.02187 = 0.02386 0.00240 -0.00097 -0.00090 C23 1 0.235445 1.145920 1.012353 11.00000 0.02291 0.02721 = 0.02186 0.00253 0.00339 0.00025 AFIX 43 H23 2 0.179460 1.110712 1.057485 11.00000 -1.20000 AFIX 0 C24 1 0.259803 1.309137 1.001356 11.00000 0.02301 0.02596 = 0.02372 -0.00164 0.00109 0.00216 C25 1 0.340627 1.359001 0.934594 11.00000 0.02657 0.01923 = 0.02546 0.00189 0.00032 0.00035 AFIX 43 H25 2 0.356459 1.469868 0.926247 11.00000 -1.20000 AFIX 0 C26 1 0.398890 1.251342 0.879751 11.00000 0.02083 0.02314 = 0.02131 0.00207 -0.00053 -0.00108 C27 1 0.261555 0.858015 0.972032 11.00000 0.03009 0.02134 = 0.03296 0.00376 0.00337 -0.00258 AFIX 137 H27A 2 0.196104 0.842552 1.019292 11.00000 -1.50000 H27B 2 0.375828 0.806489 0.976862 11.00000 -1.50000 H27C 2 0.193842 0.810795 0.928219 11.00000 -1.50000 AFIX 0 C28 1 0.200619 1.426726 1.061208 11.00000 0.04019 0.03065 = 0.02952 -0.00514 0.00808 0.00348 AFIX 137 H28A 2 0.243107 1.533923 1.048433 11.00000 -1.50000 H28B 2 0.248797 1.397929 1.111871 11.00000 -1.50000 H28C 2 0.071478 1.424767 1.062230 11.00000 -1.50000 AFIX 0 C29 1 0.485375 1.307908 0.807915 11.00000 0.03260 0.02702 = 0.02611 0.00455 0.00585 -0.00196 AFIX 137 H29A 2 0.487587 1.424600 0.807456 11.00000 -1.50000 H29B 2 0.418524 1.266358 0.762596 11.00000 -1.50000 H29C 2 0.606354 1.269615 0.806898 11.00000 -1.50000 AFIX 0 C30 1 0.436775 0.972704 0.838483 11.00000 0.02118 0.02350 = 0.02531 0.00081 -0.00072 -0.00191 C31 1 0.488981 0.873809 0.794121 11.00000 0.02346 0.02283 = 0.02557 0.00032 0.00179 -0.00267 C32 1 0.546972 0.760119 0.743241 11.00000 0.02578 0.02356 = 0.02594 0.00169 0.00293 -0.00123 C33 1 0.594076 0.661210 0.698220 11.00000 0.02904 0.02748 = 0.02594 0.00158 0.00303 0.00200 C34 1 0.646744 0.538958 0.642944 11.00000 0.03764 0.03877 = 0.03102 -0.00766 0.00317 0.00976 AFIX 137 H34A 2 0.542228 0.497096 0.614265 11.00000 -1.50000 H34B 2 0.703328 0.452178 0.670575 11.00000 -1.50000 H34C 2 0.729912 0.585807 0.607009 11.00000 -1.50000 AFIX 0 HKLF 4 REM import_a.res in P-1 REM wR2 = 0.1420, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0506 for 4166 Fo > 4sig(Fo) and 0.0605 for all 4978 data REM 261 parameters refined using 0 restraints END WGHT 0.0659 0.4878 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.307, deepest hole -0.265, 1-sigma level 0.046 Q1 1 0.6638 0.0804 0.6597 11.00000 0.05 0.31 Q2 1 1.0255 0.3477 0.2283 11.00000 0.05 0.28 Q3 1 0.6051 0.5677 0.5882 11.00000 0.05 0.26 Q4 1 0.3498 1.0596 0.9285 11.00000 0.05 0.24 Q5 1 0.4385 1.2800 0.8424 11.00000 0.05 0.24 Q6 1 0.6606 -0.0548 0.5971 11.00000 0.05 0.23 Q7 1 0.4031 1.1733 0.8900 11.00000 0.05 0.23 Q8 1 1.1580 0.9365 0.1806 11.00000 0.05 0.21 Q9 1 0.9025 0.6745 0.3778 11.00000 0.05 0.20 Q10 1 0.3105 1.0840 0.9966 11.00000 0.05 0.19 Q11 1 0.7780 0.5185 0.6337 11.00000 0.05 0.19 Q12 1 0.5540 0.4363 0.6478 11.00000 0.05 0.18 Q13 1 0.9425 0.3039 0.3103 11.00000 0.05 0.17 Q14 1 0.8533 0.7739 0.4195 11.00000 0.05 0.17 Q15 1 0.3552 1.3015 0.8997 11.00000 0.05 0.17 Q16 1 0.9273 0.8006 0.3640 11.00000 0.05 0.17 Q17 1 0.4784 0.0582 0.6230 11.00000 0.05 0.17 Q18 1 0.4874 0.9729 0.7944 11.00000 0.05 0.17 Q19 1 1.0141 0.8833 0.2287 11.00000 0.05 0.16 Q20 1 0.2402 1.3678 1.0329 11.00000 0.05 0.16 ; _shelx_res_checksum 60754 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 C1 C 0.87165(17) 0.59057(16) 0.35739(8) 0.0226(3) Uani 1 1 d . . . . . C2 C 0.87410(18) 0.75198(16) 0.38123(8) 0.0243(3) Uani 1 1 d . . . . . C3 C 0.92705(19) 0.86648(17) 0.32942(8) 0.0268(3) Uani 1 1 d . . . . . H3 H 0.927045 0.975573 0.344707 0.032 Uiso 1 1 calc R U . . . C4 C 0.98025(18) 0.82620(17) 0.25563(8) 0.0262(3) Uani 1 1 d . . . . . C5 C 0.97739(19) 0.66670(18) 0.23362(8) 0.0273(3) Uani 1 1 d . . . . . H5 H 1.014007 0.638292 0.183500 0.033 Uiso 1 1 calc R U . . . C6 C 0.92249(18) 0.54675(17) 0.28270(8) 0.0256(3) Uani 1 1 d . . . . . C7 C 0.8214(2) 0.79796(19) 0.46132(9) 0.0325(3) Uani 1 1 d . . . . . H7A H 0.831728 0.913901 0.468037 0.049 Uiso 1 1 calc R U . . . H7B H 0.899107 0.746898 0.499035 0.049 Uiso 1 1 calc R U . . . H7C H 0.699080 0.763000 0.469025 0.049 Uiso 1 1 calc R U . . . C8 C 1.0408(2) 0.9528(2) 0.20106(9) 0.0355(4) Uani 1 1 d . . . . . H8A H 0.953851 1.037189 0.198769 0.053 Uiso 1 1 calc R U . . . H8B H 1.052814 0.905481 0.149608 0.053 Uiso 1 1 calc R U . . . H8C H 1.154945 0.997861 0.219327 0.053 Uiso 1 1 calc R U . . . C9 C 0.9199(2) 0.37493(19) 0.25674(10) 0.0368(4) Uani 1 1 d . . . . . H9A H 0.922381 0.368927 0.200418 0.055 Uiso 1 1 calc R U . . . H9B H 0.812324 0.321562 0.274266 0.055 Uiso 1 1 calc R U . . . H9C H 1.023352 0.322380 0.278641 0.055 Uiso 1 1 calc R U . . . C10 C 0.81721(19) 0.47038(17) 0.40987(8) 0.0255(3) Uani 1 1 d . . . . . C11 C 0.76900(19) 0.37067(17) 0.45452(8) 0.0262(3) Uani 1 1 d . . . . . C12 C 0.71326(19) 0.25889(17) 0.50594(8) 0.0261(3) Uani 1 1 d . . . . . C13 C 0.6655(2) 0.16370(17) 0.55244(8) 0.0280(3) Uani 1 1 d . . . . . C14 C 0.6096(2) 0.0481(2) 0.60969(9) 0.0363(4) Uani 1 1 d . . . . . H14A H 0.713713 -0.000300 0.633335 0.054 Uiso 1 1 calc R U . . . H14B H 0.534585 -0.034962 0.584532 0.054 Uiso 1 1 calc R U . . . H14C H 0.543133 0.102354 0.649517 0.054 Uiso 1 1 calc R U . . . C21 C 0.37530(17) 1.08720(15) 0.89285(7) 0.0203(3) Uani 1 1 d . . . . . C22 C 0.29057(18) 1.03342(15) 0.95932(8) 0.0219(3) Uani 1 1 d . . . . . C23 C 0.23545(18) 1.14592(16) 1.01235(8) 0.0239(3) Uani 1 1 d . . . . . H23 H 0.179460 1.110712 1.057485 0.029 Uiso 1 1 calc R U . . . C24 C 0.25980(19) 1.30914(17) 1.00136(8) 0.0242(3) Uani 1 1 d . . . . . C25 C 0.34063(19) 1.35900(16) 0.93459(8) 0.0237(3) Uani 1 1 d . . . . . H25 H 0.356459 1.469868 0.926247 0.028 Uiso 1 1 calc R U . . . C26 C 0.39889(18) 1.25134(16) 0.87975(7) 0.0218(3) Uani 1 1 d . . . . . C27 C 0.2616(2) 0.85802(16) 0.97203(9) 0.0281(3) Uani 1 1 d . . . . . H27A H 0.196104 0.842552 1.019292 0.042 Uiso 1 1 calc R U . . . H27B H 0.375828 0.806489 0.976862 0.042 Uiso 1 1 calc R U . . . H27C H 0.193842 0.810795 0.928219 0.042 Uiso 1 1 calc R U . . . C28 C 0.2006(2) 1.42673(18) 1.06121(9) 0.0333(3) Uani 1 1 d . . . . . H28A H 0.243107 1.533923 1.048433 0.050 Uiso 1 1 calc R U . . . H28B H 0.248797 1.397929 1.111871 0.050 Uiso 1 1 calc R U . . . H28C H 0.071478 1.424767 1.062230 0.050 Uiso 1 1 calc R U . . . C29 C 0.4854(2) 1.30791(17) 0.80792(8) 0.0285(3) Uani 1 1 d . . . . . H29A H 0.487587 1.424600 0.807456 0.043 Uiso 1 1 calc R U . . . H29B H 0.418524 1.266358 0.762596 0.043 Uiso 1 1 calc R U . . . H29C H 0.606354 1.269615 0.806898 0.043 Uiso 1 1 calc R U . . . C30 C 0.43678(18) 0.97270(16) 0.83848(8) 0.0234(3) Uani 1 1 d . . . . . C31 C 0.48898(18) 0.87381(16) 0.79412(8) 0.0240(3) Uani 1 1 d . . . . . C32 C 0.54697(19) 0.76012(16) 0.74324(8) 0.0251(3) Uani 1 1 d . . . . . C33 C 0.5941(2) 0.66121(17) 0.69822(8) 0.0274(3) Uani 1 1 d . . . . . C34 C 0.6467(2) 0.5390(2) 0.64294(9) 0.0357(4) Uani 1 1 d . . . . . H34A H 0.542228 0.497096 0.614265 0.054 Uiso 1 1 calc R U . . . H34B H 0.703328 0.452178 0.670575 0.054 Uiso 1 1 calc R U . . . H34C H 0.729912 0.585807 0.607009 0.054 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 0.0182(6) 0.0250(7) 0.0248(7) 0.0032(5) 0.0007(5) 0.0015(5) C2 0.0199(7) 0.0263(7) 0.0271(7) 0.0015(5) 0.0015(5) 0.0036(5) C3 0.0256(7) 0.0231(7) 0.0319(7) 0.0013(5) 0.0012(6) 0.0020(5) C4 0.0200(7) 0.0304(7) 0.0283(7) 0.0058(6) 0.0003(5) -0.0013(5) C5 0.0237(7) 0.0342(8) 0.0241(7) -0.0005(6) 0.0028(5) -0.0013(6) C6 0.0200(7) 0.0277(7) 0.0289(7) -0.0013(5) 0.0016(5) 0.0001(5) C7 0.0343(8) 0.0338(8) 0.0298(7) -0.0016(6) 0.0066(6) 0.0058(6) C8 0.0333(8) 0.0374(8) 0.0359(8) 0.0115(7) 0.0031(7) -0.0045(7) C9 0.0386(9) 0.0307(8) 0.0410(9) -0.0087(7) 0.0092(7) -0.0051(7) C10 0.0223(7) 0.0258(7) 0.0285(7) 0.0016(5) 0.0002(5) 0.0024(5) C11 0.0251(7) 0.0254(7) 0.0281(7) 0.0012(5) 0.0010(5) 0.0021(5) C12 0.0280(7) 0.0243(7) 0.0260(7) -0.0010(5) 0.0016(5) 0.0012(6) C13 0.0324(8) 0.0258(7) 0.0258(7) -0.0011(5) 0.0019(6) -0.0010(6) C14 0.0442(10) 0.0374(9) 0.0274(7) 0.0052(6) 0.0053(7) -0.0059(7) C21 0.0192(6) 0.0211(6) 0.0203(6) -0.0006(5) -0.0010(5) -0.0004(5) C22 0.0199(6) 0.0219(6) 0.0239(6) 0.0024(5) -0.0010(5) -0.0009(5) C23 0.0229(7) 0.0272(7) 0.0219(6) 0.0025(5) 0.0034(5) 0.0002(5) C24 0.0230(7) 0.0260(7) 0.0237(6) -0.0016(5) 0.0011(5) 0.0022(5) C25 0.0266(7) 0.0192(6) 0.0255(7) 0.0019(5) 0.0003(5) 0.0003(5) C26 0.0208(6) 0.0231(7) 0.0213(6) 0.0021(5) -0.0005(5) -0.0011(5) C27 0.0301(8) 0.0213(7) 0.0330(7) 0.0038(5) 0.0034(6) -0.0026(6) C28 0.0402(9) 0.0306(8) 0.0295(7) -0.0051(6) 0.0081(6) 0.0035(6) C29 0.0326(8) 0.0270(7) 0.0261(7) 0.0046(5) 0.0059(6) -0.0020(6) C30 0.0212(7) 0.0235(6) 0.0253(7) 0.0008(5) -0.0007(5) -0.0019(5) C31 0.0235(7) 0.0228(6) 0.0256(7) 0.0003(5) 0.0018(5) -0.0027(5) C32 0.0258(7) 0.0236(7) 0.0259(7) 0.0017(5) 0.0029(5) -0.0012(5) C33 0.0290(7) 0.0275(7) 0.0259(7) 0.0016(6) 0.0030(6) 0.0020(6) C34 0.0376(9) 0.0388(9) 0.0310(8) -0.0077(6) 0.0032(6) 0.0098(7) 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' 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 C6 C1 C2 120.69(13) . . ? C6 C1 C10 119.86(13) . . ? C2 C1 C10 119.45(12) . . ? C3 C2 C1 118.49(13) . . ? C3 C2 C7 121.05(13) . . ? C1 C2 C7 120.46(13) . . ? C2 C3 C4 121.97(13) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 118.47(13) . . ? C5 C4 C8 120.65(13) . . ? C3 C4 C8 120.88(14) . . ? C4 C5 C6 122.10(13) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.27(13) . . ? C5 C6 C9 120.69(13) . . ? C1 C6 C9 121.04(13) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C1 178.88(15) . . ? C10 C11 C12 179.21(16) . . ? C13 C12 C11 178.36(16) . . ? C12 C13 C14 179.21(17) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C26 C21 C22 120.65(12) . . ? C26 C21 C30 120.16(12) . . ? C22 C21 C30 119.20(12) . . ? C23 C22 C21 118.47(12) . . ? C23 C22 C27 121.10(12) . . ? C21 C22 C27 120.43(12) . . ? C22 C23 C24 122.00(12) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 118.35(12) . . ? C25 C24 C28 121.55(13) . . ? C23 C24 C28 120.10(12) . . ? C26 C25 C24 121.98(12) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C25 C26 C21 118.53(12) . . ? C25 C26 C29 121.08(12) . . ? C21 C26 C29 120.39(12) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C21 178.45(15) . . ? C30 C31 C32 179.42(16) . . ? C33 C32 C31 178.65(16) . . ? C32 C33 C34 178.48(17) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 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 C1 C6 1.4099(19) . ? C1 C2 1.4109(19) . ? C1 C10 1.4323(19) . ? C2 C3 1.388(2) . ? C2 C7 1.5055(19) . ? C3 C4 1.394(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 C8 1.507(2) . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C6 C9 1.505(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.208(2) . ? C11 C12 1.374(2) . ? C12 C13 1.203(2) . ? C13 C14 1.465(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C21 C26 1.4089(18) . ? C21 C22 1.4124(18) . ? C21 C30 1.4321(18) . ? C22 C23 1.3889(19) . ? C22 C27 1.5051(18) . ? C23 C24 1.3958(19) . ? C23 H23 0.9500 . ? C24 C25 1.3926(19) . ? C24 C28 1.5075(19) . ? C25 C26 1.3913(19) . ? C25 H25 0.9500 . ? C26 C29 1.5044(18) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.2053(19) . ? C31 C32 1.3789(19) . ? C32 C33 1.199(2) . ? C33 C34 1.465(2) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 C6 C1 C2 C3 0.2(2) . . . . ? C10 C1 C2 C3 -179.91(13) . . . . ? C6 C1 C2 C7 -179.38(13) . . . . ? C10 C1 C2 C7 0.5(2) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? C7 C2 C3 C4 178.48(14) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C2 C3 C4 C8 -178.72(14) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C8 C4 C5 C6 179.89(14) . . . . ? C4 C5 C6 C1 -1.2(2) . . . . ? C4 C5 C6 C9 179.59(14) . . . . ? C2 C1 C6 C5 0.9(2) . . . . ? C10 C1 C6 C5 -178.98(13) . . . . ? C2 C1 C6 C9 -179.87(13) . . . . ? C10 C1 C6 C9 0.3(2) . . . . ? C26 C21 C22 C23 -1.7(2) . . . . ? C30 C21 C22 C23 178.51(12) . . . . ? C26 C21 C22 C27 178.43(12) . . . . ? C30 C21 C22 C27 -1.4(2) . . . . ? C21 C22 C23 C24 0.7(2) . . . . ? C27 C22 C23 C24 -179.47(13) . . . . ? C22 C23 C24 C25 0.6(2) . . . . ? C22 C23 C24 C28 -178.92(14) . . . . ? C23 C24 C25 C26 -0.8(2) . . . . ? C28 C24 C25 C26 178.69(14) . . . . ? C24 C25 C26 C21 -0.2(2) . . . . ? C24 C25 C26 C29 179.81(13) . . . . ? C22 C21 C26 C25 1.5(2) . . . . ? C30 C21 C26 C25 -178.72(13) . . . . ? C22 C21 C26 C29 -178.54(13) . . . . ? C30 C21 C26 C29 1.2(2) . . . . ?