#------------------------------------------------------------------------------ #$Date: 2024-11-21 04:27:37 +0200 (Thu, 21 Nov 2024) $ #$Revision: 296040 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249626.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_7249626 loop_ _publ_author_name 'Ponraj, Pravinkamaraj' 'Rajendran, Saravanakumar' _publ_section_title ; Design and synthesis of a novel curcumin--combretastatin A4 molecular skeleton: two pharmacophores ; _journal_issue 50 _journal_name_full 'RSC Advances' _journal_page_first 37227 _journal_page_last 37233 _journal_paper_doi 10.1039/D4RA06618A _journal_volume 14 _journal_year 2024 _chemical_formula_moiety 'C34 H30 O7' _chemical_formula_sum 'C34 H30 O7' _chemical_formula_weight 550.58 _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 mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2024-09-10 deposited with the CCDC. 2024-11-04 downloaded from the CCDC. ; _cell_angle_alpha 95.357(3) _cell_angle_beta 96.286(4) _cell_angle_gamma 107.679(3) _cell_formula_units_Z 2 _cell_length_a 9.7936(9) _cell_length_b 9.8228(8) _cell_length_c 16.0752(14) _cell_measurement_reflns_used 6000 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.61 _cell_measurement_theta_min 2.20 _cell_volume 1451.4(2) _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_unetI/netI 0.0508 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 26961 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.996 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.196 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_correction_T_min 0.5931 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.260 _exptl_crystal_description block _exptl_crystal_F_000 580 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.189 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 5126 _refine_ls_number_restraints 42 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0504 _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^)+(0.0503P)^2^+0.6868P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1154 _refine_ls_wR_factor_ref 0.1493 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3048 _reflns_number_total 5126 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra06618a3.cif _cod_data_source_block NB1 _cod_database_code 7249626 _shelx_shelxl_version_number 2014/7 _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 0.983 _shelx_estimated_absorpt_t_max 0.987 _shelx_res_file ; NB1.res created by SHELXL-2014/7 TITL NB1 in P-1 CELL 0.71073 9.7936 9.8228 16.0752 95.357 96.286 107.679 ZERR 2.00 0.0009 0.0008 0.0014 0.003 0.004 0.003 LATT 1 SFAC C H O UNIT 68 60 14 MERG 2 OMIT -3.00 50.00 OMIT 0 0 1 SADI 0.02 C31 O3 C25 O3' SADI 0.02 O3 C34 O3' C34' SIMU 0.02 0.04 O3 > C34' ISOR 0.02 0.04 O3 > C34' DFIX 0.93 0.02 C25 H25 H31 C31 EQIV $1 -x+1, -y+1, -z+2 HTAB C21 O3'_$1 EQIV $2 x-1, y, z HTAB C26 O4_$2 HTAB O2 O1 EQIV $3 -x+2, -y+1, -z+1 HTAB O2 O3_$3 HTAB O4 O5 EQIV $4 x-1, y, z+1 HTAB O6 O2_$4 HTAB O6 O7 HTAB C34' O4_$2 DFIX 2.3 0.02 H31 H30 H31 H32 FMAP 2 PLAN 20 SIZE 0.15 0.15 0.20 ACTA BOND $H CONF L.S. 4 TEMP 23.00 WGHT 0.050300 0.686800 FVAR 0.13361 0.86787 C1 1 1.422808 0.773622 0.519888 11.00000 0.05263 0.06677 = 0.03937 0.00311 0.01362 0.00859 C2 1 1.514857 0.884922 0.575880 11.00000 0.05580 0.06876 = 0.05035 0.00244 0.02014 -0.00335 AFIX 43 H2 2 1.592400 0.950846 0.557830 11.00000 -1.20000 AFIX 0 C3 1 1.493541 0.900192 0.659073 11.00000 0.04912 0.06963 = 0.04761 -0.00517 0.01244 -0.00064 AFIX 43 H3 2 1.558076 0.975684 0.696821 11.00000 -1.20000 AFIX 0 C4 1 1.377836 0.805213 0.687457 11.00000 0.04016 0.06660 = 0.04356 0.00177 0.01207 0.01127 C5 1 1.285126 0.691967 0.629465 11.00000 0.04166 0.07142 = 0.04574 0.00260 0.01512 0.00104 AFIX 43 H5 2 1.206145 0.626995 0.646876 11.00000 -1.20000 AFIX 0 C6 1 1.308250 0.674649 0.547297 11.00000 0.04363 0.06645 = 0.04214 -0.00276 0.00587 0.00353 C7 1 1.150372 0.433200 0.513639 11.00000 0.15250 0.09333 = 0.09678 -0.01156 0.00902 -0.04220 AFIX 137 H7A 2 1.218374 0.396846 0.544449 11.00000 -1.50000 H7B 2 1.099262 0.364637 0.465239 11.00000 -1.50000 H7C 2 1.082604 0.448522 0.549396 11.00000 -1.50000 AFIX 0 C8 1 1.365000 0.825307 0.776930 11.00000 0.03831 0.06911 = 0.04588 -0.00204 0.00976 0.00913 AFIX 43 H8 2 1.450092 0.880442 0.811501 11.00000 -1.20000 AFIX 0 C9 1 1.251113 0.777582 0.817536 11.00000 0.03592 0.05612 = 0.03970 -0.00025 0.00715 0.01073 C10 1 1.273000 0.812977 0.909856 11.00000 0.03156 0.06049 = 0.04154 -0.00400 0.00490 0.00755 C11 1 1.159054 0.787438 0.956425 11.00000 0.03305 0.05412 = 0.03793 0.00164 0.00775 0.01004 AFIX 43 H11 2 1.064979 0.744324 0.928679 11.00000 -1.20000 AFIX 0 C12 1 1.181620 0.824608 1.043701 11.00000 0.03592 0.04993 = 0.04304 0.00298 0.00930 0.01314 C13 1 1.059053 0.804854 1.091862 11.00000 0.03737 0.04029 = 0.04005 0.00256 0.00925 0.01169 C14 1 1.088582 0.849302 1.175359 11.00000 0.03830 0.04866 = 0.04469 0.00187 0.00938 0.01088 AFIX 43 H14 2 1.187030 0.887529 1.195573 11.00000 -1.20000 AFIX 0 C15 1 0.995930 0.849014 1.240124 11.00000 0.04485 0.04561 = 0.03800 0.00089 0.00938 0.01229 C16 1 1.061706 0.892757 1.323040 11.00000 0.04424 0.07897 = 0.04487 -0.00799 0.00490 0.01559 AFIX 43 H16 2 1.161981 0.918295 1.335271 11.00000 -1.20000 AFIX 0 C17 1 0.982237 0.899307 1.387685 11.00000 0.05265 0.10341 = 0.03802 -0.01392 0.00375 0.01588 AFIX 43 H17 2 1.028928 0.928042 1.442990 11.00000 -1.20000 AFIX 0 C18 1 0.835277 0.863923 1.371246 11.00000 0.05189 0.07703 = 0.04005 -0.00550 0.01600 0.01465 C19 1 0.766198 0.819648 1.288629 11.00000 0.04085 0.05697 = 0.04382 -0.00208 0.00934 0.00728 C20 1 0.845165 0.811388 1.224290 11.00000 0.04291 0.05264 = 0.03635 -0.00156 0.00805 0.00806 AFIX 43 H20 2 0.797786 0.780287 1.169254 11.00000 -1.20000 AFIX 0 C21 1 0.542051 0.759293 1.197887 11.00000 0.04747 0.14836 = 0.06392 0.00151 0.00004 0.01759 AFIX 137 H21A 2 0.579452 0.839870 1.168173 11.00000 -1.50000 H21B 2 0.441425 0.745000 1.201020 11.00000 -1.50000 H21C 2 0.552520 0.674234 1.168430 11.00000 -1.50000 AFIX 0 C22 1 0.912358 0.740709 1.042811 11.00000 0.03452 0.04494 = 0.03846 0.00413 0.01312 0.01102 C23 1 0.850119 0.592906 1.025367 11.00000 0.04903 0.04836 = 0.06424 0.00350 0.00873 0.01032 AFIX 43 H23 2 0.899707 0.533059 1.045899 11.00000 -1.20000 AFIX 0 C24 1 0.715985 0.533672 0.978089 11.00000 0.06282 0.06432 = 0.08876 -0.00640 0.00031 -0.00929 AFIX 43 H24 2 0.674520 0.433994 0.967405 11.00000 -1.20000 AFIX 0 C25 1 0.643189 0.619930 0.946711 11.00000 0.04989 0.10142 = 0.08549 0.00812 -0.00811 -0.00058 C26 1 0.702622 0.765343 0.962646 11.00000 0.05114 0.09930 = 0.08058 0.03012 0.00580 0.02903 AFIX 43 H26 2 0.652691 0.824280 0.941247 11.00000 -1.20000 AFIX 0 C27 1 0.836997 0.825579 1.010552 11.00000 0.04323 0.05639 = 0.06593 0.01297 0.00863 0.01450 AFIX 43 H27 2 0.877268 0.925378 1.021195 11.00000 -1.20000 AFIX 0 C28 1 1.099951 0.699768 0.777076 11.00000 0.03842 0.05010 = 0.03492 0.00224 0.00894 0.01182 C29 1 1.040801 0.552330 0.771496 11.00000 0.04406 0.05094 = 0.05726 0.00843 0.00134 0.01658 AFIX 43 H29 2 1.099140 0.498468 0.789364 11.00000 -1.20000 AFIX 0 C30 1 0.897956 0.483213 0.740214 11.00000 0.05105 0.04285 = 0.06342 0.00787 0.00189 0.01010 AFIX 43 H30 2 0.860852 0.383378 0.736375 11.00000 -1.20000 AFIX 0 C31 1 0.809939 0.560150 0.714685 11.00000 0.03887 0.05140 = 0.05175 -0.00236 0.00309 0.00643 C32 1 0.866366 0.706148 0.718181 11.00000 0.05139 0.05803 = 0.08791 0.00720 -0.00777 0.02383 AFIX 43 H32 2 0.807654 0.759434 0.699962 11.00000 -1.20000 AFIX 0 C33 1 1.010789 0.774423 0.748831 11.00000 0.04971 0.04189 = 0.07681 0.00534 -0.00058 0.00944 AFIX 43 H33 2 1.048523 0.873819 0.750330 11.00000 -1.20000 AFIX 0 O1 3 1.225333 0.565209 0.486871 11.00000 0.06882 0.08764 = 0.05237 -0.00914 0.01622 -0.01746 O2 3 1.447942 0.759404 0.438185 11.00000 0.07345 0.08445 = 0.04232 -0.00182 0.02063 -0.00487 AFIX 83 H2A 2 1.385394 0.688674 0.411278 11.00000 -1.50000 AFIX 0 O4 3 1.404626 0.871122 0.946895 11.00000 0.03692 0.12789 = 0.04391 -0.01380 0.00766 0.00629 AFIX 83 H4 2 1.405038 0.887041 0.997928 11.00000 -1.50000 AFIX 0 O5 3 1.311579 0.880642 1.084230 11.00000 0.03589 0.10002 = 0.04432 -0.00509 0.00540 0.01136 O6 3 0.757521 0.872294 1.435547 11.00000 0.06139 0.14586 = 0.04509 -0.01619 0.01783 0.02286 AFIX 83 H6 2 0.671112 0.847515 1.416662 11.00000 -1.50000 AFIX 0 O7 3 0.619563 0.786876 1.280216 11.00000 0.04116 0.10603 = 0.04986 -0.00532 0.01152 0.00899 PART 1 O3 3 0.668975 0.481090 0.685480 21.00000 0.03447 0.06118 = 0.07494 -0.00307 -0.00363 0.00785 C34 1 0.567761 0.556876 0.673163 21.00000 0.04609 0.09236 = 0.17539 0.00122 -0.01980 0.02531 AFIX 33 H34A 2 0.473394 0.489527 0.652671 21.00000 -1.50000 H34B 2 0.565193 0.610265 0.725806 21.00000 -1.50000 H34C 2 0.596140 0.622168 0.632670 21.00000 -1.50000 AFIX 0 PART 2 O3' 3 0.544265 0.514498 0.884501 -21.00000 0.08426 0.08609 = 0.10671 0.00396 -0.02330 0.03084 C34' 1 0.461050 0.579654 0.835640 -21.00000 0.09342 0.11916 = 0.09664 0.00525 -0.03619 0.02721 AFIX 33 H34D 2 0.393755 0.508176 0.793326 -21.00000 -1.50000 H34E 2 0.408807 0.622957 0.871269 -21.00000 -1.50000 H34F 2 0.523543 0.652492 0.808831 -21.00000 -1.50000 AFIX 0 PART 1 H25 2 0.545467 0.593600 0.921769 21.00000 -1.20000 PART 2 H31 2 0.710060 0.519111 0.712346 -21.00000 -1.20000 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM NB1 in P-1 REM R1 = 0.0504 for 3048 Fo > 4sig(Fo) and 0.1024 for all 5126 data REM 397 parameters refined using 42 restraints END WGHT 0.0503 0.6868 REM Highest difference peak 0.189, deepest hole -0.208, 1-sigma level 0.039 Q1 1 1.2668 0.4142 0.4963 11.00000 0.05 0.19 Q2 1 0.6006 0.5749 0.6048 11.00000 0.05 0.16 Q3 1 1.3791 0.8619 1.0487 11.00000 0.05 0.15 Q4 1 1.0379 0.3880 0.4573 11.00000 0.05 0.14 Q5 1 1.1954 0.8667 1.3250 11.00000 0.05 0.14 Q6 1 1.5507 1.0279 0.7097 11.00000 0.05 0.13 Q7 1 0.7818 0.7697 0.7444 11.00000 0.05 0.13 Q8 1 0.7504 0.8454 1.1493 11.00000 0.05 0.13 Q9 1 1.0198 0.8684 0.7959 11.00000 0.05 0.12 Q10 1 0.9971 0.5304 0.5499 11.00000 0.05 0.12 Q11 1 0.5874 0.7483 1.1297 11.00000 0.05 0.12 Q12 1 1.2372 0.9266 1.2093 11.00000 0.05 0.12 Q13 1 0.4582 0.8545 1.2399 11.00000 0.05 0.12 Q14 1 1.5176 0.8773 0.8205 11.00000 0.05 0.11 Q15 1 1.2586 0.9387 1.0628 11.00000 0.05 0.11 Q16 1 0.6333 0.5629 0.5406 11.00000 0.05 0.11 Q17 1 1.3157 0.7152 0.8009 11.00000 0.05 0.11 Q18 1 1.0223 0.7830 1.2069 11.00000 0.05 0.11 Q19 1 1.1890 0.7237 0.9956 11.00000 0.05 0.11 Q20 1 1.1959 0.6795 0.4668 11.00000 0.05 0.11 ; _shelx_res_checksum 19701 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 1.4228(3) 0.7736(3) 0.51989(17) 0.0550(7) Uani 1 1 d . . . . . C2 C 1.5149(3) 0.8849(3) 0.57588(18) 0.0630(8) Uani 1 1 d . . . . . H2 H 1.5924 0.9508 0.5578 0.076 Uiso 1 1 calc R U . . . C3 C 1.4935(3) 0.9002(3) 0.65907(17) 0.0603(8) Uani 1 1 d . . . . . H3 H 1.5581 0.9757 0.6968 0.072 Uiso 1 1 calc R U . . . C4 C 1.3778(3) 0.8052(3) 0.68746(16) 0.0513(7) Uani 1 1 d . . . . . C5 C 1.2851(3) 0.6920(3) 0.62947(17) 0.0564(8) Uani 1 1 d . . . . . H5 H 1.2061 0.6270 0.6469 0.068 Uiso 1 1 calc R U . . . C6 C 1.3082(3) 0.6746(3) 0.54730(17) 0.0546(7) Uani 1 1 d . . . . . C7 C 1.1504(5) 0.4332(4) 0.5136(3) 0.1350(19) Uani 1 1 d . . . . . H7A H 1.2184 0.3968 0.5444 0.203 Uiso 1 1 calc R U . . . H7B H 1.0993 0.3646 0.4652 0.203 Uiso 1 1 calc R U . . . H7C H 1.0826 0.4485 0.5494 0.203 Uiso 1 1 calc R U . . . C8 C 1.3650(3) 0.8253(3) 0.77693(17) 0.0533(7) Uani 1 1 d . . . . . H8 H 1.4501 0.8804 0.8115 0.064 Uiso 1 1 calc R U . . . C9 C 1.2511(3) 0.7776(3) 0.81754(15) 0.0451(6) Uani 1 1 d . . . . . C10 C 1.2730(3) 0.8130(3) 0.90986(16) 0.0469(7) Uani 1 1 d . . . . . C11 C 1.1591(3) 0.7874(3) 0.95643(15) 0.0427(6) Uani 1 1 d . . . . . H11 H 1.0650 0.7443 0.9287 0.051 Uiso 1 1 calc R U . . . C12 C 1.1816(3) 0.8246(3) 1.04370(16) 0.0430(6) Uani 1 1 d . . . . . C13 C 1.0591(2) 0.8049(3) 1.09186(15) 0.0393(6) Uani 1 1 d . . . . . C14 C 1.0886(3) 0.8493(3) 1.17536(16) 0.0446(6) Uani 1 1 d . . . . . H14 H 1.1870 0.8875 1.1956 0.053 Uiso 1 1 calc R U . . . C15 C 0.9959(3) 0.8490(3) 1.24012(15) 0.0433(6) Uani 1 1 d . . . . . C16 C 1.0617(3) 0.8928(3) 1.32304(17) 0.0581(8) Uani 1 1 d . . . . . H16 H 1.1620 0.9183 1.3353 0.070 Uiso 1 1 calc R U . . . C17 C 0.9822(3) 0.8993(4) 1.38768(18) 0.0685(9) Uani 1 1 d . . . . . H17 H 1.0289 0.9280 1.4430 0.082 Uiso 1 1 calc R U . . . C18 C 0.8353(3) 0.8639(3) 1.37125(17) 0.0578(8) Uani 1 1 d . . . . . C19 C 0.7662(3) 0.8196(3) 1.28863(16) 0.0494(7) Uani 1 1 d . . . . . C20 C 0.8452(3) 0.8114(3) 1.22429(16) 0.0459(6) Uani 1 1 d . . . . . H20 H 0.7978 0.7803 1.1693 0.055 Uiso 1 1 calc R U . . . C21 C 0.5421(3) 0.7593(5) 1.1979(2) 0.0911(12) Uani 1 1 d . . . . . H21A H 0.5795 0.8399 1.1682 0.137 Uiso 1 1 calc R U . . . H21B H 0.4414 0.7450 1.2010 0.137 Uiso 1 1 calc R U . . . H21C H 0.5525 0.6742 1.1684 0.137 Uiso 1 1 calc R U . . . C22 C 0.9124(2) 0.7407(3) 1.04281(15) 0.0391(6) Uani 1 1 d . . . . . C23 C 0.8501(3) 0.5929(3) 1.02537(18) 0.0553(7) Uani 1 1 d . . . . . H23 H 0.8997 0.5331 1.0459 0.066 Uiso 1 1 calc R U . . . C24 C 0.7160(4) 0.5337(4) 0.9781(2) 0.0806(10) Uani 1 1 d . . . . . H24 H 0.6745 0.4340 0.9674 0.097 Uiso 1 1 calc R U . . . C25 C 0.6432(4) 0.6199(5) 0.9467(2) 0.0862(11) Uani 1 1 d D . . . . C26 C 0.7026(3) 0.7653(4) 0.9626(2) 0.0749(10) Uani 1 1 d . . . . . H26 H 0.6527 0.8243 0.9412 0.090 Uiso 1 1 calc R U . . . C27 C 0.8370(3) 0.8256(3) 1.01055(18) 0.0551(7) Uani 1 1 d . . . . . H27 H 0.8773 0.9254 1.0212 0.066 Uiso 1 1 calc R U . . . C28 C 1.1000(3) 0.6998(3) 0.77708(15) 0.0416(6) Uani 1 1 d . . . . . C29 C 1.0408(3) 0.5523(3) 0.77150(17) 0.0508(7) Uani 1 1 d . . . . . H29 H 1.0991 0.4985 0.7894 0.061 Uiso 1 1 calc R U . . . C30 C 0.8980(3) 0.4832(3) 0.74021(17) 0.0540(7) Uani 1 1 d . . . . . H30 H 0.8609 0.3834 0.7364 0.065 Uiso 1 1 calc DR U . . . C31 C 0.8099(3) 0.5602(3) 0.71468(17) 0.0500(7) Uani 1 1 d D . . . . C32 C 0.8664(3) 0.7061(3) 0.7182(2) 0.0659(9) Uani 1 1 d . . . . . H32 H 0.8077 0.7594 0.7000 0.079 Uiso 1 1 calc DR U . . . C33 C 1.0108(3) 0.7744(3) 0.74883(19) 0.0582(8) Uani 1 1 d . . . . . H33 H 1.0485 0.8738 0.7503 0.070 Uiso 1 1 calc R U . . . O1 O 1.2253(2) 0.5652(2) 0.48687(12) 0.0799(7) Uani 1 1 d . . . . . O2 O 1.4479(2) 0.7594(2) 0.43819(11) 0.0733(6) Uani 1 1 d . . . . . H2A H 1.3854 0.6887 0.4113 0.110 Uiso 1 1 calc R U . . . O4 O 1.40463(19) 0.8711(2) 0.94690(12) 0.0756(7) Uani 1 1 d . . . . . H4 H 1.4050 0.8870 0.9979 0.113 Uiso 1 1 calc R U . . . O5 O 1.31158(18) 0.8806(2) 1.08423(11) 0.0634(6) Uani 1 1 d . . . . . O6 O 0.7575(2) 0.8723(3) 1.43555(12) 0.0875(8) Uani 1 1 d . . . . . H6 H 0.6711 0.8475 1.4167 0.131 Uiso 1 1 calc R U . . . O7 O 0.61956(19) 0.7869(2) 1.28022(12) 0.0696(6) Uani 1 1 d . . . . . O3 O 0.6690(2) 0.4811(2) 0.68548(15) 0.0603(8) Uani 0.868(4) 1 d D U P A 1 C34 C 0.5678(4) 0.5569(5) 0.6732(3) 0.1078(18) Uani 0.868(4) 1 d D U P A 1 H34A H 0.4734 0.4895 0.6527 0.162 Uiso 0.868(4) 1 calc R U P A 1 H34B H 0.5652 0.6103 0.7258 0.162 Uiso 0.868(4) 1 calc R U P A 1 H34C H 0.5961 0.6222 0.6327 0.162 Uiso 0.868(4) 1 calc R U P A 1 O3' O 0.5443(19) 0.5145(18) 0.8845(12) 0.095(7) Uani 0.132(4) 1 d D U P A 2 C34' C 0.461(3) 0.580(3) 0.8356(18) 0.109(10) Uani 0.132(4) 1 d D U P A 2 H34D H 0.3938 0.5082 0.7933 0.164 Uiso 0.132(4) 1 calc R U P A 2 H34E H 0.4088 0.6230 0.8713 0.164 Uiso 0.132(4) 1 calc R U P A 2 H34F H 0.5235 0.6525 0.8088 0.164 Uiso 0.132(4) 1 calc R U P A 2 H25 H 0.545(3) 0.594(6) 0.922(3) 0.131 Uiso 0.868(4) 1 d D U P A 1 H31 H 0.710(4) 0.519(10) 0.71(2) 0.131 Uiso 0.132(4) 1 d D U P A 2 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 0.0526(17) 0.0668(19) 0.0394(16) 0.0031(14) 0.0136(13) 0.0086(15) C2 0.0558(18) 0.069(2) 0.0503(18) 0.0024(15) 0.0201(14) -0.0034(15) C3 0.0491(17) 0.070(2) 0.0476(17) -0.0052(14) 0.0124(13) -0.0006(15) C4 0.0402(15) 0.0666(19) 0.0436(16) 0.0018(14) 0.0121(12) 0.0113(14) C5 0.0417(16) 0.071(2) 0.0457(17) 0.0026(14) 0.0151(13) 0.0010(14) C6 0.0436(16) 0.0665(19) 0.0421(16) -0.0028(14) 0.0059(13) 0.0035(14) C7 0.152(4) 0.093(3) 0.097(3) -0.012(3) 0.009(3) -0.042(3) C8 0.0383(15) 0.0691(19) 0.0459(16) -0.0020(14) 0.0098(12) 0.0091(14) C9 0.0359(14) 0.0561(17) 0.0397(15) -0.0003(12) 0.0071(11) 0.0107(12) C10 0.0316(14) 0.0605(17) 0.0415(15) -0.0040(13) 0.0049(11) 0.0075(12) C11 0.0330(14) 0.0541(16) 0.0379(15) 0.0016(12) 0.0078(11) 0.0100(12) C12 0.0359(15) 0.0499(16) 0.0430(16) 0.0030(12) 0.0093(12) 0.0131(12) C13 0.0374(14) 0.0403(14) 0.0401(15) 0.0026(11) 0.0092(11) 0.0117(11) C14 0.0383(14) 0.0487(16) 0.0447(16) 0.0019(12) 0.0094(12) 0.0109(12) C15 0.0448(15) 0.0456(15) 0.0380(15) 0.0009(12) 0.0094(12) 0.0123(12) C16 0.0442(16) 0.079(2) 0.0449(17) -0.0080(14) 0.0049(13) 0.0156(15) C17 0.0527(19) 0.103(3) 0.0380(16) -0.0139(16) 0.0037(14) 0.0159(17) C18 0.0519(18) 0.077(2) 0.0401(16) -0.0055(14) 0.0160(13) 0.0146(15) C19 0.0409(15) 0.0570(17) 0.0438(16) -0.0021(13) 0.0093(12) 0.0073(13) C20 0.0429(15) 0.0526(16) 0.0363(14) -0.0016(12) 0.0080(12) 0.0081(13) C21 0.0475(19) 0.148(4) 0.064(2) 0.002(2) 0.0000(16) 0.018(2) C22 0.0345(14) 0.0449(15) 0.0385(14) 0.0041(11) 0.0131(11) 0.0110(12) C23 0.0490(17) 0.0484(17) 0.0642(19) 0.0035(14) 0.0087(14) 0.0103(14) C24 0.063(2) 0.064(2) 0.089(3) -0.0064(19) 0.0003(19) -0.0093(18) C25 0.050(2) 0.101(3) 0.085(3) 0.008(2) -0.0081(18) -0.001(2) C26 0.051(2) 0.099(3) 0.081(2) 0.030(2) 0.0058(17) 0.029(2) C27 0.0432(16) 0.0564(18) 0.0659(19) 0.0130(15) 0.0086(14) 0.0145(14) C28 0.0384(14) 0.0501(16) 0.0349(14) 0.0022(12) 0.0089(11) 0.0118(13) C29 0.0441(16) 0.0509(17) 0.0573(18) 0.0084(13) 0.0013(13) 0.0166(14) C30 0.0510(18) 0.0429(16) 0.0634(19) 0.0079(14) 0.0019(14) 0.0101(14) C31 0.0389(15) 0.0514(17) 0.0517(17) -0.0024(13) 0.0031(13) 0.0064(14) C32 0.0514(18) 0.058(2) 0.088(2) 0.0072(16) -0.0078(16) 0.0238(16) C33 0.0497(18) 0.0419(16) 0.077(2) 0.0053(14) -0.0006(15) 0.0094(14) O1 0.0688(14) 0.0876(16) 0.0524(13) -0.0091(11) 0.0162(11) -0.0175(12) O2 0.0734(14) 0.0844(15) 0.0423(12) -0.0018(10) 0.0206(10) -0.0049(12) O4 0.0369(11) 0.1279(19) 0.0439(11) -0.0138(12) 0.0077(9) 0.0063(11) O5 0.0359(11) 0.1000(16) 0.0443(11) -0.0051(10) 0.0054(8) 0.0114(10) O6 0.0614(14) 0.146(2) 0.0451(12) -0.0162(13) 0.0178(10) 0.0229(14) O7 0.0412(11) 0.1060(17) 0.0499(12) -0.0053(11) 0.0115(9) 0.0090(11) O3 0.0345(12) 0.0612(15) 0.0749(18) -0.0031(12) -0.0036(11) 0.0078(11) C34 0.046(2) 0.092(3) 0.175(5) 0.001(3) -0.020(3) 0.025(2) O3' 0.084(11) 0.086(12) 0.107(13) 0.004(9) -0.023(9) 0.031(9) C34' 0.093(18) 0.12(2) 0.097(19) 0.005(16) -0.036(15) 0.027(16) 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' O O 0.0106 0.0060 '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 O2 119.1(2) . . ? C2 C1 C6 119.6(2) . . ? O2 C1 C6 121.2(2) . . ? C1 C2 C3 120.3(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 117.8(2) . . ? C3 C4 C8 118.1(2) . . ? C5 C4 C8 124.1(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? O1 C6 C5 125.1(2) . . ? O1 C6 C1 115.0(2) . . ? C5 C6 C1 120.0(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C4 130.7(2) . . ? C9 C8 H8 114.7 . . ? C4 C8 H8 114.7 . . ? C8 C9 C10 118.1(2) . . ? C8 C9 C28 125.7(2) . . ? C10 C9 C28 116.1(2) . . ? O4 C10 C11 120.4(2) . . ? O4 C10 C9 117.1(2) . . ? C11 C10 C9 122.5(2) . . ? C10 C11 C12 121.7(2) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? O5 C12 C11 120.5(2) . . ? O5 C12 C13 118.4(2) . . ? C11 C12 C13 121.2(2) . . ? C14 C13 C12 118.0(2) . . ? C14 C13 C22 125.5(2) . . ? C12 C13 C22 116.5(2) . . ? C13 C14 C15 132.2(2) . . ? C13 C14 H14 113.9 . . ? C15 C14 H14 113.9 . . ? C16 C15 C20 117.6(2) . . ? C16 C15 C14 117.8(2) . . ? C20 C15 C14 124.6(2) . . ? C17 C16 C15 121.5(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? O6 C18 C17 120.0(2) . . ? O6 C18 C19 120.5(2) . . ? C17 C18 C19 119.5(2) . . ? O7 C19 C20 125.7(2) . . ? O7 C19 C18 114.1(2) . . ? C20 C19 C18 120.2(2) . . ? C19 C20 C15 120.9(2) . . ? C19 C20 H20 119.5 . . ? C15 C20 H20 119.5 . . ? O7 C21 H21A 109.5 . . ? O7 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O7 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 118.1(2) . . ? C27 C22 C13 121.2(2) . . ? C23 C22 C13 120.6(2) . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 120.1(3) . . ? C26 C25 O3' 139.0(8) . . ? C24 C25 O3' 97.2(8) . . ? C26 C25 H25 111(3) . . ? C24 C25 H25 128(4) . . ? C25 C26 C27 119.9(3) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C22 C27 C26 121.0(3) . . ? C22 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C33 C28 C29 117.3(2) . . ? C33 C28 C9 120.5(2) . . ? C29 C28 C9 122.1(2) . . ? C30 C29 C28 121.5(3) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C31 C30 C29 120.3(3) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 119.4(2) . . ? C30 C31 O3 115.6(2) . . ? C32 C31 O3 124.9(3) . . ? C30 C31 H31 119(4) . . ? C32 C31 H31 119(4) . . ? C31 C32 C33 119.8(3) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C28 C33 C32 121.7(3) . . ? C28 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? C6 O1 C7 117.8(2) . . ? C1 O2 H2A 109.5 . . ? C10 O4 H4 109.5 . . ? C18 O6 H6 109.5 . . ? C19 O7 C21 118.0(2) . . ? C31 O3 C34 117.7(3) . . ? O3 C34 H34A 109.5 . . ? O3 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O3 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C34' O3' C25 109.3(17) . . ? O3' C34' H34D 109.5 . . ? O3' C34' H34E 109.5 . . ? H34D C34' H34E 109.5 . . ? O3' C34' H34F 109.5 . . ? H34D C34' H34F 109.5 . . ? H34E C34' H34F 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 C2 1.363(4) . ? C1 O2 1.365(3) . ? C1 C6 1.387(4) . ? C2 C3 1.377(4) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.392(4) . ? C4 C8 1.458(4) . ? C5 C6 1.368(4) . ? C5 H5 0.9300 . ? C6 O1 1.364(3) . ? C7 O1 1.414(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.337(3) . ? C8 H8 0.9300 . ? C9 C10 1.469(3) . ? C9 C28 1.486(3) . ? C10 O4 1.290(3) . ? C10 C11 1.384(3) . ? C11 C12 1.392(3) . ? C11 H11 0.9300 . ? C12 O5 1.294(3) . ? C12 C13 1.472(3) . ? C13 C14 1.343(3) . ? C13 C22 1.481(3) . ? C14 C15 1.454(3) . ? C14 H14 0.9300 . ? C15 C16 1.383(4) . ? C15 C20 1.396(3) . ? C16 C17 1.373(4) . ? C16 H16 0.9300 . ? C17 C18 1.363(4) . ? C17 H17 0.9300 . ? C18 O6 1.360(3) . ? C18 C19 1.388(4) . ? C19 O7 1.361(3) . ? C19 C20 1.368(3) . ? C20 H20 0.9300 . ? C21 O7 1.410(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C27 1.371(3) . ? C22 C23 1.381(3) . ? C23 C24 1.370(4) . ? C23 H23 0.9300 . ? C24 C25 1.360(5) . ? C24 H24 0.9300 . ? C25 C26 1.356(5) . ? C25 O3' 1.413(14) . ? C25 H25 0.94(2) . ? C26 C27 1.377(4) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C33 1.368(4) . ? C28 C29 1.377(3) . ? C29 C30 1.370(3) . ? C29 H29 0.9300 . ? C30 C31 1.363(4) . ? C30 H30 0.9300 . ? C31 C32 1.365(4) . ? C31 O3 1.367(3) . ? C31 H31 0.933(18) . ? C32 C33 1.379(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? O2 H2A 0.8200 . ? O4 H4 0.8200 . ? O6 H6 0.8200 . ? O3 C34 1.417(4) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? O3' C34' 1.400(18) . ? C34' H34D 0.9600 . ? C34' H34E 0.9600 . ? C34' H34F 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C21 H21C O3' 0.96 1.88 2.722(17) 145.5 2_667 C26 H26 O4 0.93 2.62 3.375(4) 139.2 1_455 O2 H2A O1 0.82 2.22 2.670(3) 114.6 . O2 H2A O3 0.82 2.07 2.797(3) 147.9 2_766 O4 H4 O5 0.82 1.74 2.483(3) 149.9 . O6 H6 O2 0.82 2.17 2.902(3) 148.2 1_456 O6 H6 O7 0.82 2.18 2.636(3) 115.2 . C34' H34E O4 0.96 2.63 3.45(3) 143.4 1_455 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 O2 C1 C2 C3 -178.8(3) . . . . ? C6 C1 C2 C3 -0.7(5) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 C8 178.0(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C8 C4 C5 C6 -176.1(3) . . . . ? C4 C5 C6 O1 178.3(3) . . . . ? C4 C5 C6 C1 -2.2(5) . . . . ? C2 C1 C6 O1 -178.1(3) . . . . ? O2 C1 C6 O1 -0.1(4) . . . . ? C2 C1 C6 C5 2.3(5) . . . . ? O2 C1 C6 C5 -179.7(3) . . . . ? C3 C4 C8 C9 160.6(3) . . . . ? C5 C4 C8 C9 -22.8(5) . . . . ? C4 C8 C9 C10 178.4(3) . . . . ? C4 C8 C9 C28 -6.3(5) . . . . ? C8 C9 C10 O4 -9.1(4) . . . . ? C28 C9 C10 O4 175.1(2) . . . . ? C8 C9 C10 C11 170.3(3) . . . . ? C28 C9 C10 C11 -5.5(4) . . . . ? O4 C10 C11 C12 0.8(4) . . . . ? C9 C10 C11 C12 -178.6(2) . . . . ? C10 C11 C12 O5 -2.1(4) . . . . ? C10 C11 C12 C13 176.3(2) . . . . ? O5 C12 C13 C14 1.5(4) . . . . ? C11 C12 C13 C14 -176.9(2) . . . . ? O5 C12 C13 C22 179.8(2) . . . . ? C11 C12 C13 C22 1.4(4) . . . . ? C12 C13 C14 C15 178.6(3) . . . . ? C22 C13 C14 C15 0.4(5) . . . . ? C13 C14 C15 C16 174.8(3) . . . . ? C13 C14 C15 C20 -7.0(5) . . . . ? C20 C15 C16 C17 -0.1(4) . . . . ? C14 C15 C16 C17 178.2(3) . . . . ? C15 C16 C17 C18 -0.7(5) . . . . ? C16 C17 C18 O6 -179.2(3) . . . . ? C16 C17 C18 C19 0.7(5) . . . . ? O6 C18 C19 O7 -0.3(4) . . . . ? C17 C18 C19 O7 179.8(3) . . . . ? O6 C18 C19 C20 -179.9(3) . . . . ? C17 C18 C19 C20 0.1(5) . . . . ? O7 C19 C20 C15 179.4(3) . . . . ? C18 C19 C20 C15 -0.9(4) . . . . ? C16 C15 C20 C19 0.9(4) . . . . ? C14 C15 C20 C19 -177.3(3) . . . . ? C14 C13 C22 C27 86.6(3) . . . . ? C12 C13 C22 C27 -91.5(3) . . . . ? C14 C13 C22 C23 -96.1(3) . . . . ? C12 C13 C22 C23 85.8(3) . . . . ? C27 C22 C23 C24 -0.9(4) . . . . ? C13 C22 C23 C24 -178.3(3) . . . . ? C22 C23 C24 C25 0.9(5) . . . . ? C23 C24 C25 C26 -0.5(6) . . . . ? C23 C24 C25 O3' 161.9(10) . . . . ? C24 C25 C26 C27 0.1(6) . . . . ? O3' C25 C26 C27 -152.7(15) . . . . ? C23 C22 C27 C26 0.5(4) . . . . ? C13 C22 C27 C26 177.8(3) . . . . ? C25 C26 C27 C22 -0.1(5) . . . . ? C8 C9 C28 C33 -83.7(4) . . . . ? C10 C9 C28 C33 91.8(3) . . . . ? C8 C9 C28 C29 100.8(3) . . . . ? C10 C9 C28 C29 -83.8(3) . . . . ? C33 C28 C29 C30 -1.0(4) . . . . ? C9 C28 C29 C30 174.7(2) . . . . ? C28 C29 C30 C31 -0.9(4) . . . . ? C29 C30 C31 C32 2.0(4) . . . . ? C29 C30 C31 O3 -179.2(2) . . . . ? C30 C31 C32 C33 -1.2(5) . . . . ? O3 C31 C32 C33 -179.9(3) . . . . ? C29 C28 C33 C32 1.8(4) . . . . ? C9 C28 C33 C32 -173.9(3) . . . . ? C31 C32 C33 C28 -0.8(5) . . . . ? C5 C6 O1 C7 -26.8(5) . . . . ? C1 C6 O1 C7 153.7(4) . . . . ? C20 C19 O7 C21 -8.5(4) . . . . ? C18 C19 O7 C21 171.8(3) . . . . ? C30 C31 O3 C34 168.5(3) . . . . ? C32 C31 O3 C34 -12.8(5) . . . . ? C26 C25 O3' C34' -18(3) . . . . ? C24 C25 O3' C34' -175(2) . . . . ?