#------------------------------------------------------------------------------ #$Date: 2026-05-30 02:27:21 +0100 (Sat, 30 May 2026) $ #$Revision: 306138 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577320.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_1577320 loop_ _publ_author_name 'Pal, Uttam' 'Woolard, Reed M.' 'Rout, Priyanka' 'Samal, Sanket' 'Kuila, Suman' 'Rahat, Md Masudur Rahman' 'Shen, Guancheng' 'Laskin, Julia' 'Barlow, Stephen' 'Marder, Seth R.' 'Hutchison, Geoffrey R.' 'Mei, Jianguo' _publ_section_title ; Poly(chromenochromenedione) (PCCD): a structural isomer of poly(benzodifurandione) (PBDF) ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D6PY00313C _journal_year 2026 _chemical_formula_sum 'C34 H26 O8' _chemical_formula_weight 562.55 _chemical_name_systematic CCD2 _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 _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/ccdc.csd.cc2r7b9n _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2026-03-19 deposited with the CCDC. 2026-05-21 downloaded from the CCDC. ; _cell_angle_alpha 76.704(4) _cell_angle_beta 81.939(5) _cell_angle_gamma 85.572(7) _cell_formula_units_Z 2 _cell_length_a 6.7456(7) _cell_length_b 10.5361(11) _cell_length_c 19.3370(18) _cell_measurement_reflns_used 9844 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 79.7050 _cell_measurement_theta_min 4.3166 _cell_volume 1322.8(2) _computing_cell_refinement 'SAINT V8.40B (Bruker, 2020)' _computing_data_collection 'Apex5 v2023.9-2 (Bruker, 2023)' _computing_data_reduction 'SAINT V8.40B (Bruker, 2020)' _computing_structure_refinement ; SHELXL-2019/2 (Sheldrick, 2015a, 2019), SHELXLE Rev1613 (H\"ubschle et al., 2011) ; _computing_structure_solution 'SHELXT (Sheldrick, 2015b)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 7.4074 _diffrn_detector_type 'PhotonIII_C14 charge-integrating and photon counting pixel array' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device 'four circle diffractometer' _diffrn_measurement_device_type 'Bruker AXS D8 Quest' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator 'HELIOS multilayer Montel optics' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 42376 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 80.360 _diffrn_reflns_theta_min 4.316 _diffrn_source 'I-mu-S 3.0 microsource X-ray tube' _diffrn_source_current '1.1 mA' _diffrn_source_voltage '50 kV' _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_T_max 0.754304 _exptl_absorpt_correction_T_min 0.610260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D. (2015). J. Appl. Cryst. 48 3-10. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.412 _exptl_crystal_description fragment _exptl_crystal_F_000 588 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Dichloromethane/Hexanes' _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.189 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 386 _refine_ls_number_reflns 5771 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0479 _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^)+(0.1131P)^2^+0.1466P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1498 _refine_ls_wR_factor_ref 0.1557 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5266 _reflns_number_total 5771 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6py00313c2.cif _cod_data_source_block o_CCD2_0m_5 _cod_database_code 1577320 _shelx_shelxl_version_number 2019/3 _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 0.706 _shelx_estimated_absorpt_t_max 0.967 _shelx_res_file ; TITL o_CCD2_0m_a.res in P-1 o_CCD2_0m_5.res created by SHELXL-2019/3 at 10:10:57 on 27-Jul-2024 REM Old TITL o_CCD2_0m in P-1 REM SHELXT solution in P-1: R1 0.249, Rweak 0.033, Alpha 0.128 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C33 O9 CELL 1.54178 6.7456 10.5361 19.3370 76.7039 81.9385 85.5718 ZERR 2.000 0.0007 0.0011 0.0018 0.0041 0.0054 0.0070 LATT 1 SFAC C H O UNIT 68 52 16 TEMP -123.150 SIZE 0.45 0.11 0.04 L.S. 10 BOND $H ACTA CONF LIST 4 FMAP 2 PLAN 20 REM EXTI 0.001262 WGHT 0.113100 0.146600 BASF 0.40298 FVAR 0.44651 O2 3 1.132713 0.469926 0.398427 11.00000 0.03590 0.03656 = 0.03001 -0.00042 -0.00282 0.01140 O3 3 0.945207 0.752399 0.166276 11.00000 0.03335 0.03955 = 0.02518 -0.00355 -0.00275 0.00684 O4 3 0.653008 0.840690 0.198638 11.00000 0.03719 0.04370 = 0.02841 0.00082 -0.00476 0.01149 O5 3 0.140951 0.831186 0.386760 11.00000 0.02446 0.03150 = 0.02809 -0.00541 -0.00730 0.00302 O6 3 -0.151698 0.918029 0.419123 11.00000 0.02628 0.04014 = 0.03145 -0.00373 -0.00888 0.00281 O7 3 0.126793 0.746797 0.653977 11.00000 0.02327 0.03419 = 0.02661 -0.00908 -0.00506 0.00597 O8 3 0.377735 0.616411 0.625046 11.00000 0.03381 0.03368 = 0.02613 -0.00437 -0.00557 0.01055 O1 3 0.862755 0.578068 0.432810 11.00000 0.02895 0.02888 = 0.02472 -0.00484 -0.00464 0.00545 C2 1 0.684999 0.646910 0.419342 11.00000 0.02742 0.02047 = 0.02625 -0.00496 -0.00574 0.00187 C3 1 0.647438 0.702509 0.348982 11.00000 0.02920 0.02026 = 0.02517 -0.00622 -0.00516 -0.00031 C4 1 0.458059 0.764121 0.340515 11.00000 0.03064 0.02485 = 0.02479 -0.00504 -0.00668 -0.00008 AFIX 43 H4 2 0.422371 0.801046 0.294035 11.00000 -1.20000 AFIX 0 C5 1 0.324267 0.770435 0.400518 11.00000 0.02729 0.02208 = 0.02806 -0.00592 -0.00725 0.00125 C6 1 0.365610 0.721521 0.471035 11.00000 0.02888 0.01895 = 0.02608 -0.00546 -0.00462 0.00006 C7 1 1.003258 0.549195 0.380014 11.00000 0.02997 0.02379 = 0.02524 -0.00504 -0.00402 -0.00028 C8 1 0.982956 0.620218 0.305163 11.00000 0.03114 0.02158 = 0.02507 -0.00612 -0.00566 -0.00078 C9 1 0.808870 0.693170 0.291604 11.00000 0.02975 0.02223 = 0.02531 -0.00584 -0.00453 -0.00133 C10 1 0.789398 0.767406 0.217740 11.00000 0.03181 0.02898 = 0.02507 -0.00548 -0.00437 0.00159 C11 1 1.118043 0.676845 0.178819 11.00000 0.03073 0.03057 = 0.02829 -0.00663 -0.00507 0.00255 C12 1 1.145955 0.609293 0.248548 11.00000 0.03205 0.02535 = 0.02681 -0.00736 -0.00237 -0.00181 C13 1 1.327273 0.536872 0.258233 11.00000 0.03303 0.03732 = 0.02972 -0.00815 -0.00581 0.00224 AFIX 43 H13 2 1.352297 0.491125 0.304813 11.00000 -1.20000 AFIX 0 C14 1 1.468972 0.532214 0.200075 11.00000 0.03332 0.04612 = 0.03478 -0.00892 -0.00489 0.00735 AFIX 43 H14 2 1.591182 0.482632 0.206955 11.00000 -1.20000 AFIX 0 C15 1 1.435964 0.599019 0.131354 11.00000 0.03618 0.05117 = 0.03127 -0.01056 0.00071 0.00555 AFIX 43 H15 2 1.536510 0.593910 0.092304 11.00000 -1.20000 AFIX 0 C16 1 1.259380 0.673173 0.118326 11.00000 0.03696 0.04168 = 0.02711 -0.00626 -0.00217 0.00404 C17 1 1.224652 0.750242 0.042662 11.00000 0.04439 0.07405 = 0.02591 0.00201 0.00142 0.01238 C18 1 1.397172 0.720837 -0.013620 11.00000 0.06970 0.13617 = 0.02802 0.00511 0.00863 0.03830 AFIX 137 H18A 2 1.369983 0.768517 -0.061430 11.00000 -1.50000 H18B 2 1.407886 0.626904 -0.011912 11.00000 -1.50000 H18C 2 1.523264 0.748408 -0.003279 11.00000 -1.50000 AFIX 0 C19 1 1.218629 0.896584 0.040012 11.00000 0.06801 0.06712 = 0.05536 0.02195 0.00349 0.00525 AFIX 137 H19A 2 1.205507 0.945511 -0.008903 11.00000 -1.50000 H19B 2 1.342715 0.918709 0.054558 11.00000 -1.50000 H19C 2 1.103806 0.919361 0.072681 11.00000 -1.50000 AFIX 0 C20 1 1.030610 0.712447 0.021408 11.00000 0.06254 0.11657 = 0.03075 -0.02261 -0.01479 0.01592 AFIX 137 H20A 2 1.019773 0.755039 -0.028701 11.00000 -1.50000 H20B 2 0.915529 0.740621 0.052156 11.00000 -1.50000 H20C 2 1.032411 0.617506 0.027175 11.00000 -1.50000 AFIX 0 C21 1 -0.003217 0.858774 0.439105 11.00000 0.02351 0.02375 = 0.02863 -0.00408 -0.00614 -0.00375 C22 1 0.035681 0.812199 0.514714 11.00000 0.02427 0.01949 = 0.02897 -0.00454 -0.00689 -0.00087 C23 1 0.214849 0.745148 0.528434 11.00000 0.02614 0.01987 = 0.02620 -0.00496 -0.00584 -0.00115 C24 1 0.250904 0.695902 0.603817 11.00000 0.02588 0.02410 = 0.02617 -0.00609 -0.00387 0.00038 C25 1 -0.054862 0.810349 0.641685 11.00000 0.02171 0.02282 = 0.02944 -0.00512 -0.00662 -0.00083 C26 1 -0.112075 0.839243 0.572614 11.00000 0.02464 0.02157 = 0.02901 -0.00545 -0.00451 -0.00398 C27 1 -0.306426 0.895205 0.564381 11.00000 0.02556 0.02684 = 0.03291 -0.00573 -0.00819 -0.00105 AFIX 43 H27 2 -0.352090 0.914933 0.518636 11.00000 -1.20000 AFIX 0 C28 1 -0.430038 0.921166 0.623280 11.00000 0.02580 0.03139 = 0.03684 -0.00618 -0.00604 0.00166 AFIX 43 H28 2 -0.562535 0.956190 0.618046 11.00000 -1.20000 AFIX 0 C29 1 -0.362958 0.896669 0.690210 11.00000 0.02270 0.03004 = 0.03340 -0.00727 0.00003 -0.00084 AFIX 43 H29 2 -0.450662 0.917675 0.729330 11.00000 -1.20000 AFIX 0 C30 1 -0.172344 0.842581 0.702065 11.00000 0.02401 0.02637 = 0.02836 -0.00423 -0.00247 -0.00236 C31 1 -0.095128 0.825631 0.774786 11.00000 0.02492 0.03538 = 0.02749 -0.00830 -0.00260 -0.00046 C32 1 0.086696 0.909122 0.765413 11.00000 0.05017 0.06290 = 0.03388 -0.01259 -0.00613 -0.02456 AFIX 137 H32A 2 0.196757 0.875809 0.734640 11.00000 -1.50000 H32B 2 0.129111 0.905222 0.812329 11.00000 -1.50000 H32C 2 0.050657 0.999800 0.743269 11.00000 -1.50000 AFIX 0 C33 1 -0.039052 0.683012 0.807226 11.00000 0.05957 0.03957 = 0.03559 -0.00505 -0.01557 0.00410 AFIX 137 H33A 2 0.062278 0.648943 0.773733 11.00000 -1.50000 H33B 2 -0.158563 0.631398 0.816370 11.00000 -1.50000 H33C 2 0.015056 0.677322 0.852360 11.00000 -1.50000 AFIX 0 C34 1 -0.256097 0.871741 0.828995 11.00000 0.04224 0.08309 = 0.03121 -0.01781 -0.00230 0.01905 AFIX 137 H34A 2 -0.293634 0.963928 0.810914 11.00000 -1.50000 H34B 2 -0.203315 0.861285 0.874785 11.00000 -1.50000 H34C 2 -0.374304 0.819505 0.835960 11.00000 -1.50000 AFIX 0 C1 1 0.553197 0.656550 0.479575 11.00000 0.02997 0.02159 = 0.02396 -0.00382 -0.00552 -0.00019 AFIX 43 H1 2 0.588948 0.619779 0.526062 11.00000 -1.20000 REM ##### REM REM C:/Users/zelle/Desktop/o_CCD2/o_CCD2_0m_5.hkl REM AFIX 0 HKLF 5 REM o_CCD2_0m_a.res in P-1 REM wR2 = 0.1557, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0479 for 5266 Fo > 4sig(Fo) and 0.0522 for all 5771 data REM 386 parameters refined using 0 restraints END WGHT 0.1130 0.1448 REM Highest difference peak 0.189, deepest hole -0.226, 1-sigma level 0.053 Q1 1 0.0017 0.8264 0.4783 11.00000 0.05 0.19 Q2 1 -0.4095 0.7822 0.5730 11.00000 0.05 0.19 Q3 1 0.6625 0.6734 0.3840 11.00000 0.05 0.18 Q4 1 -0.3061 1.0281 0.6002 11.00000 0.05 0.17 Q5 1 -0.3853 0.9399 0.6493 11.00000 0.05 0.17 Q6 1 0.2391 0.7214 0.5648 11.00000 0.05 0.17 Q7 1 0.6964 0.7758 0.4507 11.00000 0.05 0.17 Q8 1 0.2047 1.1019 0.6772 11.00000 0.05 0.17 Q9 1 0.3341 0.7478 0.4388 11.00000 0.05 0.17 Q10 1 1.4524 0.5660 0.1788 11.00000 0.05 0.16 Q11 1 -0.5021 1.0346 0.6330 11.00000 0.05 0.16 Q12 1 -0.5517 0.8368 0.6114 11.00000 0.05 0.16 Q13 1 1.6848 0.4041 0.1786 11.00000 0.05 0.16 Q14 1 0.0094 0.7407 0.4183 11.00000 0.05 0.16 Q15 1 0.2673 0.7018 0.7800 11.00000 0.05 0.16 Q16 1 -0.6251 1.1148 0.6118 11.00000 0.05 0.15 Q17 1 0.7596 0.6822 0.5475 11.00000 0.05 0.15 Q18 1 1.0121 0.5011 0.2478 11.00000 0.05 0.15 Q19 1 0.3860 0.5843 0.5731 11.00000 0.05 0.15 Q20 1 1.1438 0.3841 0.3472 11.00000 0.05 0.15 ; _shelx_res_checksum 91424 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 O2 O 1.1327(2) 0.46993(15) 0.39843(7) 0.0361(3) Uani 1 1 d . . . . . O3 O 0.9452(2) 0.75240(15) 0.16628(7) 0.0338(3) Uani 1 1 d . . . . . O4 O 0.6530(2) 0.84069(16) 0.19864(7) 0.0385(4) Uani 1 1 d . . . . . O5 O 0.14095(19) 0.83119(13) 0.38676(7) 0.0281(3) Uani 1 1 d . . . . . O6 O -0.1517(2) 0.91803(15) 0.41912(7) 0.0330(3) Uani 1 1 d . . . . . O7 O 0.12679(19) 0.74680(14) 0.65398(7) 0.0278(3) Uani 1 1 d . . . . . O8 O 0.3777(2) 0.61641(14) 0.62505(7) 0.0321(3) Uani 1 1 d . . . . . O1 O 0.8628(2) 0.57807(13) 0.43281(7) 0.0279(3) Uani 1 1 d . . . . . C2 C 0.6850(3) 0.64691(17) 0.41934(10) 0.0247(4) Uani 1 1 d . . . . . C3 C 0.6474(3) 0.70251(17) 0.34898(9) 0.0246(3) Uani 1 1 d . . . . . C4 C 0.4581(3) 0.76412(18) 0.34052(10) 0.0266(4) Uani 1 1 d . . . . . H4 H 0.422371 0.801046 0.294035 0.032 Uiso 1 1 calc R U . . . C5 C 0.3243(3) 0.77044(18) 0.40052(10) 0.0255(4) Uani 1 1 d . . . . . C6 C 0.3656(3) 0.72152(17) 0.47103(9) 0.0245(4) Uani 1 1 d . . . . . C7 C 1.0033(3) 0.54919(18) 0.38001(10) 0.0264(4) Uani 1 1 d . . . . . C8 C 0.9830(3) 0.62022(17) 0.30516(9) 0.0256(4) Uani 1 1 d . . . . . C9 C 0.8089(3) 0.69317(17) 0.29160(9) 0.0256(4) Uani 1 1 d . . . . . C10 C 0.7894(3) 0.76741(19) 0.21774(10) 0.0288(4) Uani 1 1 d . . . . . C11 C 1.1180(3) 0.6768(2) 0.17882(10) 0.0299(4) Uani 1 1 d . . . . . C12 C 1.1460(3) 0.60929(19) 0.24855(10) 0.0279(4) Uani 1 1 d . . . . . C13 C 1.3273(3) 0.5369(2) 0.25823(11) 0.0333(4) Uani 1 1 d . . . . . H13 H 1.352297 0.491125 0.304813 0.040 Uiso 1 1 calc R U . . . C14 C 1.4690(3) 0.5322(2) 0.20008(12) 0.0385(5) Uani 1 1 d . . . . . H14 H 1.591182 0.482632 0.206955 0.046 Uiso 1 1 calc R U . . . C15 C 1.4360(3) 0.5990(2) 0.13135(11) 0.0402(5) Uani 1 1 d . . . . . H15 H 1.536510 0.593910 0.092304 0.048 Uiso 1 1 calc R U . . . C16 C 1.2594(3) 0.6732(2) 0.11833(11) 0.0360(5) Uani 1 1 d . . . . . C17 C 1.2247(4) 0.7502(3) 0.04266(12) 0.0516(7) Uani 1 1 d . . . . . C18 C 1.3972(6) 0.7208(5) -0.01362(14) 0.0855(14) Uani 1 1 d . . . . . H18A H 1.369983 0.768517 -0.061430 0.128 Uiso 1 1 calc R U . . . H18B H 1.407886 0.626904 -0.011912 0.128 Uiso 1 1 calc R U . . . H18C H 1.523264 0.748408 -0.003279 0.128 Uiso 1 1 calc R U . . . C19 C 1.2186(5) 0.8966(3) 0.04001(17) 0.0709(10) Uani 1 1 d . . . . . H19A H 1.205507 0.945511 -0.008903 0.106 Uiso 1 1 calc R U . . . H19B H 1.342715 0.918709 0.054558 0.106 Uiso 1 1 calc R U . . . H19C H 1.103806 0.919361 0.072681 0.106 Uiso 1 1 calc R U . . . C20 C 1.0306(5) 0.7124(4) 0.02141(14) 0.0691(10) Uani 1 1 d . . . . . H20A H 1.019773 0.755039 -0.028701 0.104 Uiso 1 1 calc R U . . . H20B H 0.915529 0.740621 0.052156 0.104 Uiso 1 1 calc R U . . . H20C H 1.032411 0.617506 0.027175 0.104 Uiso 1 1 calc R U . . . C21 C -0.0032(3) 0.85877(18) 0.43910(10) 0.0252(4) Uani 1 1 d . . . . . C22 C 0.0357(3) 0.81220(17) 0.51471(10) 0.0240(3) Uani 1 1 d . . . . . C23 C 0.2148(3) 0.74515(17) 0.52843(9) 0.0238(4) Uani 1 1 d . . . . . C24 C 0.2509(3) 0.69590(18) 0.60382(9) 0.0253(4) Uani 1 1 d . . . . . C25 C -0.0549(3) 0.81035(17) 0.64169(10) 0.0244(4) Uani 1 1 d . . . . . C26 C -0.1121(3) 0.83924(18) 0.57261(10) 0.0248(4) Uani 1 1 d . . . . . C27 C -0.3064(3) 0.89521(19) 0.56438(10) 0.0282(4) Uani 1 1 d . . . . . H27 H -0.352090 0.914933 0.518636 0.034 Uiso 1 1 calc R U . . . C28 C -0.4300(3) 0.9212(2) 0.62328(11) 0.0315(4) Uani 1 1 d . . . . . H28 H -0.562535 0.956190 0.618046 0.038 Uiso 1 1 calc R U . . . C29 C -0.3630(3) 0.89667(19) 0.69021(10) 0.0290(4) Uani 1 1 d . . . . . H29 H -0.450662 0.917675 0.729330 0.035 Uiso 1 1 calc R U . . . C30 C -0.1723(3) 0.84258(19) 0.70207(10) 0.0266(4) Uani 1 1 d . . . . . C31 C -0.0951(3) 0.8256(2) 0.77479(10) 0.0292(4) Uani 1 1 d . . . . . C32 C 0.0867(4) 0.9091(3) 0.76541(12) 0.0474(6) Uani 1 1 d . . . . . H32A H 0.196757 0.875809 0.734640 0.071 Uiso 1 1 calc R U . . . H32B H 0.129111 0.905222 0.812329 0.071 Uiso 1 1 calc R U . . . H32C H 0.050657 0.999800 0.743269 0.071 Uiso 1 1 calc R U . . . C33 C -0.0391(4) 0.6830(2) 0.80723(12) 0.0449(5) Uani 1 1 d . . . . . H33A H 0.062278 0.648943 0.773733 0.067 Uiso 1 1 calc R U . . . H33B H -0.158563 0.631398 0.816370 0.067 Uiso 1 1 calc R U . . . H33C H 0.015056 0.677322 0.852360 0.067 Uiso 1 1 calc R U . . . C34 C -0.2561(4) 0.8717(3) 0.82900(12) 0.0527(7) Uani 1 1 d . . . . . H34A H -0.293634 0.963928 0.810914 0.079 Uiso 1 1 calc R U . . . H34B H -0.203315 0.861285 0.874785 0.079 Uiso 1 1 calc R U . . . H34C H -0.374304 0.819505 0.835960 0.079 Uiso 1 1 calc R U . . . C1 C 0.5532(3) 0.65655(17) 0.47957(9) 0.0252(4) Uani 1 1 d . . . . . H1 H 0.588948 0.619779 0.526062 0.030 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 O2 0.0359(7) 0.0366(8) 0.0300(6) -0.0004(6) -0.0028(6) 0.0114(6) O3 0.0333(7) 0.0396(8) 0.0252(6) -0.0036(5) -0.0027(5) 0.0068(6) O4 0.0372(8) 0.0437(8) 0.0284(7) 0.0008(6) -0.0048(6) 0.0115(6) O5 0.0245(6) 0.0315(7) 0.0281(6) -0.0054(5) -0.0073(5) 0.0030(5) O6 0.0263(7) 0.0401(8) 0.0315(7) -0.0037(6) -0.0089(5) 0.0028(6) O7 0.0233(6) 0.0342(7) 0.0266(6) -0.0091(5) -0.0051(5) 0.0060(5) O8 0.0338(7) 0.0337(7) 0.0261(6) -0.0044(5) -0.0056(5) 0.0105(6) O1 0.0290(7) 0.0289(7) 0.0247(6) -0.0048(5) -0.0046(5) 0.0055(5) C2 0.0274(9) 0.0205(8) 0.0262(8) -0.0050(6) -0.0057(7) 0.0019(7) C3 0.0292(8) 0.0203(8) 0.0252(8) -0.0062(6) -0.0052(7) -0.0003(6) C4 0.0306(9) 0.0249(8) 0.0248(8) -0.0050(6) -0.0067(7) -0.0001(7) C5 0.0273(9) 0.0221(8) 0.0281(8) -0.0059(6) -0.0073(7) 0.0013(7) C6 0.0289(9) 0.0190(8) 0.0261(8) -0.0055(6) -0.0046(7) 0.0001(7) C7 0.0300(9) 0.0238(8) 0.0252(8) -0.0050(7) -0.0040(7) -0.0003(7) C8 0.0311(9) 0.0216(8) 0.0251(8) -0.0061(6) -0.0057(7) -0.0008(7) C9 0.0297(9) 0.0222(8) 0.0253(8) -0.0058(6) -0.0045(7) -0.0013(7) C10 0.0318(9) 0.0290(9) 0.0251(8) -0.0055(7) -0.0044(7) 0.0016(7) C11 0.0307(10) 0.0306(9) 0.0283(9) -0.0066(7) -0.0051(7) 0.0025(8) C12 0.0321(9) 0.0253(8) 0.0268(8) -0.0074(7) -0.0024(7) -0.0018(7) C13 0.0330(10) 0.0373(11) 0.0297(9) -0.0081(7) -0.0058(7) 0.0022(8) C14 0.0333(10) 0.0461(12) 0.0348(10) -0.0089(9) -0.0049(8) 0.0073(9) C15 0.0362(11) 0.0512(13) 0.0313(10) -0.0106(9) 0.0007(8) 0.0056(10) C16 0.0370(10) 0.0417(11) 0.0271(9) -0.0063(8) -0.0022(8) 0.0040(9) C17 0.0444(13) 0.0741(18) 0.0259(10) 0.0020(10) 0.0014(9) 0.0124(12) C18 0.070(2) 0.136(4) 0.0280(11) 0.0051(15) 0.0086(12) 0.038(2) C19 0.0680(18) 0.0671(19) 0.0554(16) 0.0219(15) 0.0035(14) 0.0053(15) C20 0.0625(18) 0.117(3) 0.0307(11) -0.0226(14) -0.0148(11) 0.0159(19) C21 0.0235(8) 0.0238(8) 0.0286(8) -0.0041(6) -0.0061(6) -0.0038(7) C22 0.0243(8) 0.0195(8) 0.0290(8) -0.0045(6) -0.0069(7) -0.0009(6) C23 0.0261(9) 0.0199(8) 0.0262(8) -0.0050(6) -0.0058(7) -0.0011(7) C24 0.0259(8) 0.0241(8) 0.0262(8) -0.0061(7) -0.0039(6) 0.0004(7) C25 0.0217(8) 0.0228(8) 0.0294(8) -0.0051(6) -0.0066(6) -0.0008(6) C26 0.0246(8) 0.0216(8) 0.0290(8) -0.0054(6) -0.0045(7) -0.0040(6) C27 0.0256(9) 0.0268(9) 0.0329(9) -0.0057(7) -0.0082(7) -0.0011(7) C28 0.0258(9) 0.0314(10) 0.0368(9) -0.0062(7) -0.0060(7) 0.0017(7) C29 0.0227(8) 0.0300(9) 0.0334(9) -0.0073(7) 0.0000(7) -0.0008(7) C30 0.0240(8) 0.0264(9) 0.0284(8) -0.0042(7) -0.0025(7) -0.0024(7) C31 0.0249(9) 0.0354(10) 0.0275(8) -0.0083(7) -0.0026(7) -0.0005(7) C32 0.0502(13) 0.0629(15) 0.0339(10) -0.0126(10) -0.0061(9) -0.0246(12) C33 0.0596(15) 0.0396(12) 0.0356(10) -0.0051(9) -0.0156(10) 0.0041(11) C34 0.0422(12) 0.083(2) 0.0312(10) -0.0178(11) -0.0023(9) 0.0190(13) C1 0.0300(9) 0.0216(8) 0.0240(7) -0.0038(6) -0.0055(7) -0.0002(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' O O 0.0492 0.0322 '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 C10 O3 C11 124.84(15) . . ? C21 O5 C5 123.31(15) . . ? C24 O7 C25 123.65(15) . . ? C7 O1 C2 123.06(15) . . ? O1 C2 C1 114.93(16) . . ? O1 C2 C3 120.85(16) . . ? C1 C2 C3 124.21(17) . . ? C4 C3 C2 116.64(16) . . ? C4 C3 C9 125.94(16) . . ? C2 C3 C9 117.41(17) . . ? C5 C4 C3 119.08(16) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 O5 114.85(16) . . ? C4 C5 C6 124.36(17) . . ? O5 C5 C6 120.79(16) . . ? C5 C6 C1 116.58(16) . . ? C5 C6 C23 117.67(16) . . ? C1 C6 C23 125.74(17) . . ? O2 C7 O1 116.65(16) . . ? O2 C7 C8 126.05(17) . . ? O1 C7 C8 117.30(16) . . ? C9 C8 C12 122.06(17) . . ? C9 C8 C7 118.65(17) . . ? C12 C8 C7 119.28(16) . . ? C8 C9 C3 121.18(17) . . ? C8 C9 C10 119.13(17) . . ? C3 C9 C10 119.64(16) . . ? O4 C10 O3 116.72(16) . . ? O4 C10 C9 126.72(18) . . ? O3 C10 C9 116.54(16) . . ? O3 C11 C12 120.37(17) . . ? O3 C11 C16 115.98(17) . . ? C12 C11 C16 123.64(18) . . ? C13 C12 C11 117.75(17) . . ? C13 C12 C8 125.29(17) . . ? C11 C12 C8 116.96(17) . . ? C14 C13 C12 119.87(19) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 121.1(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 121.77(19) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C15 C16 C11 115.88(18) . . ? C15 C16 C17 121.93(18) . . ? C11 C16 C17 122.16(18) . . ? C19 C17 C20 110.6(3) . . ? C19 C17 C16 109.5(2) . . ? C20 C17 C16 111.1(2) . . ? C19 C17 C18 107.6(3) . . ? C20 C17 C18 107.1(3) . . ? C16 C17 C18 110.8(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O6 C21 O5 116.19(16) . . ? O6 C21 C22 126.04(17) . . ? O5 C21 C22 117.77(15) . . ? C23 C22 C26 121.20(17) . . ? C23 C22 C21 118.64(16) . . ? C26 C22 C21 120.15(16) . . ? C22 C23 C6 121.58(16) . . ? C22 C23 C24 118.51(16) . . ? C6 C23 C24 119.90(16) . . ? O8 C24 O7 117.10(16) . . ? O8 C24 C23 126.42(17) . . ? O7 C24 C23 116.48(15) . . ? O7 C25 C26 120.08(16) . . ? O7 C25 C30 115.53(15) . . ? C26 C25 C30 124.39(16) . . ? C25 C26 C27 117.47(17) . . ? C25 C26 C22 117.40(16) . . ? C27 C26 C22 125.11(17) . . ? C28 C27 C26 119.56(18) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C29 120.87(18) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C28 C29 C30 122.59(18) . . ? C28 C29 H29 118.7 . . ? C30 C29 H29 118.7 . . ? C29 C30 C25 114.88(17) . . ? C29 C30 C31 121.90(17) . . ? C25 C30 C31 123.16(16) . . ? C33 C31 C32 109.99(19) . . ? C33 C31 C34 106.74(18) . . ? C32 C31 C34 107.9(2) . . ? C33 C31 C30 112.29(18) . . ? C32 C31 C30 109.03(16) . . ? C34 C31 C30 110.74(17) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C2 C1 C6 118.96(16) . . ? C2 C1 H1 120.5 . . ? C6 C1 H1 120.5 . . ? 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 O2 C7 1.194(2) . ? O3 C10 1.369(2) . ? O3 C11 1.378(2) . ? O4 C10 1.197(2) . ? O5 C21 1.368(2) . ? O5 C5 1.379(2) . ? O6 C21 1.201(2) . ? O7 C24 1.368(2) . ? O7 C25 1.374(2) . ? O8 C24 1.197(2) . ? O1 C7 1.364(2) . ? O1 C2 1.378(2) . ? C2 C1 1.381(2) . ? C2 C3 1.402(2) . ? C3 C4 1.401(3) . ? C3 C9 1.456(2) . ? C4 C5 1.378(2) . ? C4 H4 0.9500 . ? C5 C6 1.401(2) . ? C6 C1 1.404(3) . ? C6 C23 1.449(2) . ? C7 C8 1.488(2) . ? C8 C9 1.376(3) . ? C8 C12 1.457(3) . ? C9 C10 1.481(2) . ? C11 C12 1.403(3) . ? C11 C16 1.408(3) . ? C12 C13 1.403(3) . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.393(3) . ? C14 H14 0.9500 . ? C15 C16 1.394(3) . ? C15 H15 0.9500 . ? C16 C17 1.541(3) . ? C17 C19 1.528(5) . ? C17 C20 1.532(5) . ? C17 C18 1.542(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.485(2) . ? C22 C23 1.379(2) . ? C22 C26 1.455(2) . ? C23 C24 1.478(2) . ? C25 C26 1.402(2) . ? C25 C30 1.410(2) . ? C26 C27 1.410(3) . ? C27 C28 1.382(3) . ? C27 H27 0.9500 . ? C28 C29 1.392(3) . ? C28 H28 0.9500 . ? C29 C30 1.393(3) . ? C29 H29 0.9500 . ? C30 C31 1.535(3) . ? C31 C33 1.530(3) . ? C31 C32 1.530(3) . ? C31 C34 1.532(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C1 H1 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 C7 O1 C2 C1 174.30(17) . . . . ? C7 O1 C2 C3 -6.3(3) . . . . ? O1 C2 C3 C4 176.43(16) . . . . ? C1 C2 C3 C4 -4.2(3) . . . . ? O1 C2 C3 C9 -4.6(3) . . . . ? C1 C2 C3 C9 174.77(18) . . . . ? C2 C3 C4 C5 2.1(3) . . . . ? C9 C3 C4 C5 -176.78(18) . . . . ? C3 C4 C5 O5 -179.09(16) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C21 O5 C5 C4 -173.02(17) . . . . ? C21 O5 C5 C6 6.3(3) . . . . ? C4 C5 C6 C1 -3.3(3) . . . . ? O5 C5 C6 C1 177.44(16) . . . . ? C4 C5 C6 C23 175.08(18) . . . . ? O5 C5 C6 C23 -4.2(3) . . . . ? C2 O1 C7 O2 -166.82(19) . . . . ? C2 O1 C7 C8 13.9(3) . . . . ? O2 C7 C8 C9 170.0(2) . . . . ? O1 C7 C8 C9 -10.9(3) . . . . ? O2 C7 C8 C12 -9.3(3) . . . . ? O1 C7 C8 C12 169.86(17) . . . . ? C12 C8 C9 C3 179.83(17) . . . . ? C7 C8 C9 C3 0.6(3) . . . . ? C12 C8 C9 C10 -2.6(3) . . . . ? C7 C8 C9 C10 178.19(17) . . . . ? C4 C3 C9 C8 -174.05(18) . . . . ? C2 C3 C9 C8 7.1(3) . . . . ? C4 C3 C9 C10 8.4(3) . . . . ? C2 C3 C9 C10 -170.49(17) . . . . ? C11 O3 C10 O4 177.08(19) . . . . ? C11 O3 C10 C9 -1.8(3) . . . . ? C8 C9 C10 O4 -175.3(2) . . . . ? C3 C9 C10 O4 2.3(3) . . . . ? C8 C9 C10 O3 3.4(3) . . . . ? C3 C9 C10 O3 -178.94(17) . . . . ? C10 O3 C11 C12 -0.8(3) . . . . ? C10 O3 C11 C16 179.27(19) . . . . ? O3 C11 C12 C13 -178.29(19) . . . . ? C16 C11 C12 C13 1.6(3) . . . . ? O3 C11 C12 C8 1.8(3) . . . . ? C16 C11 C12 C8 -178.3(2) . . . . ? C9 C8 C12 C13 -179.95(19) . . . . ? C7 C8 C12 C13 -0.7(3) . . . . ? C9 C8 C12 C11 0.0(3) . . . . ? C7 C8 C12 C11 179.20(17) . . . . ? C11 C12 C13 C14 -1.1(3) . . . . ? C8 C12 C13 C14 178.8(2) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C14 C15 C16 C11 0.4(4) . . . . ? C14 C15 C16 C17 178.3(3) . . . . ? O3 C11 C16 C15 178.6(2) . . . . ? C12 C11 C16 C15 -1.2(3) . . . . ? O3 C11 C16 C17 0.7(3) . . . . ? C12 C11 C16 C17 -179.1(2) . . . . ? C15 C16 C17 C19 -112.7(3) . . . . ? C11 C16 C17 C19 65.1(3) . . . . ? C15 C16 C17 C20 124.9(3) . . . . ? C11 C16 C17 C20 -57.3(3) . . . . ? C15 C16 C17 C18 5.9(4) . . . . ? C11 C16 C17 C18 -176.3(3) . . . . ? C5 O5 C21 O6 176.27(17) . . . . ? C5 O5 C21 C22 -4.4(3) . . . . ? O6 C21 C22 C23 179.94(19) . . . . ? O5 C21 C22 C23 0.7(3) . . . . ? O6 C21 C22 C26 -1.0(3) . . . . ? O5 C21 C22 C26 179.73(16) . . . . ? C26 C22 C23 C6 -177.94(17) . . . . ? C21 C22 C23 C6 1.1(3) . . . . ? C26 C22 C23 C24 2.6(3) . . . . ? C21 C22 C23 C24 -178.42(16) . . . . ? C5 C6 C23 C22 0.6(3) . . . . ? C1 C6 C23 C22 178.81(18) . . . . ? C5 C6 C23 C24 -179.90(17) . . . . ? C1 C6 C23 C24 -1.7(3) . . . . ? C25 O7 C24 O8 -161.93(18) . . . . ? C25 O7 C24 C23 18.2(3) . . . . ? C22 C23 C24 O8 164.75(19) . . . . ? C6 C23 C24 O8 -14.7(3) . . . . ? C22 C23 C24 O7 -15.4(3) . . . . ? C6 C23 C24 O7 165.12(17) . . . . ? C24 O7 C25 C26 -7.3(3) . . . . ? C24 O7 C25 C30 172.86(17) . . . . ? O7 C25 C26 C27 175.10(16) . . . . ? C30 C25 C26 C27 -5.1(3) . . . . ? O7 C25 C26 C22 -6.4(3) . . . . ? C30 C25 C26 C22 173.36(17) . . . . ? C23 C22 C26 C25 8.4(3) . . . . ? C21 C22 C26 C25 -170.64(17) . . . . ? C23 C22 C26 C27 -173.31(18) . . . . ? C21 C22 C26 C27 7.7(3) . . . . ? C25 C26 C27 C28 1.1(3) . . . . ? C22 C26 C27 C28 -177.25(19) . . . . ? C26 C27 C28 C29 2.1(3) . . . . ? C27 C28 C29 C30 -1.6(3) . . . . ? C28 C29 C30 C25 -2.1(3) . . . . ? C28 C29 C30 C31 175.37(19) . . . . ? O7 C25 C30 C29 -174.68(16) . . . . ? C26 C25 C30 C29 5.5(3) . . . . ? O7 C25 C30 C31 7.9(3) . . . . ? C26 C25 C30 C31 -171.90(18) . . . . ? C29 C30 C31 C33 120.8(2) . . . . ? C25 C30 C31 C33 -61.9(3) . . . . ? C29 C30 C31 C32 -117.0(2) . . . . ? C25 C30 C31 C32 60.2(3) . . . . ? C29 C30 C31 C34 1.6(3) . . . . ? C25 C30 C31 C34 178.8(2) . . . . ? O1 C2 C1 C6 -178.06(16) . . . . ? C3 C2 C1 C6 2.5(3) . . . . ? C5 C6 C1 C2 1.2(3) . . . . ? C23 C6 C1 C2 -177.00(18) . . . . ?