#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:19:49 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257999 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240553.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_7240553 loop_ _publ_author_name 'Zeng, Ziyu' 'Qasem, Ashraf M. A.' 'Kociok-K\"ohn, Gabriele' 'Rowan, Michael G.' 'Blagbrough, Ian S.' _publ_section_title ; The 1\a-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers ; _journal_issue 32 _journal_name_full 'RSC Advances' _journal_page_first 18797 _journal_page_last 18805 _journal_paper_doi 10.1039/D0RA03811C _journal_volume 10 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C33 H45 N O11' _chemical_formula_sum 'C33 H45 N O11' _chemical_formula_weight 631.70 _chemical_name_common mesaconitine _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-17 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.70194(13) _cell_length_b 15.37677(17) _cell_length_c 15.55588(17) _cell_measurement_reflns_used 35001 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 73.0660 _cell_measurement_theta_min 4.0280 _cell_volume 3038.29(6) _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _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) Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _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 0.996 _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 0.0347 _diffrn_reflns_av_unetI/netI 0.0159 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 55167 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.372 _diffrn_reflns_theta_min 4.042 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.857 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.381 _exptl_crystal_description prism _exptl_crystal_F_000 1352 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc/DCM' _exptl_crystal_size_max 0.282 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.116 _refine_diff_density_max 0.182 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details ; Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 424 _refine_ls_number_reflns 6062 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0268 _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^)+(0.0385P)^2^+0.5749P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.0683 _reflns_Friedel_coverage 0.781 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.991 _reflns_number_gt 5983 _reflns_number_total 6062 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03811c2.cif _cod_data_source_block mesaconitine _cod_depositor_comments 'Adding full bibliography for 7240553--7240554.cif.' _cod_database_code 7240553 _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 0.794 _shelx_estimated_absorpt_t_max 0.907 _oxdiff_exptl_absorpt_empirical_full_min 0.773 _oxdiff_exptl_absorpt_empirical_full_max 1.235 _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)2(1)2(1) s20phar2.res created by SHELXL-2018/3 at 11:47:20 on 05-Mar-2020 CELL 1.54184 12.70194 15.37677 15.55588 90.000 90.000 90.000 ZERR 4.00 0.00013 0.00017 0.00017 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 132 180 4 44 ACTA FMAP 2 PLAN 5 BOND $H CONF EQIV $2 -x+1, y+1/2, -z+1/2 HTAB O3 O4 HTAB O5 O7 HTAB O10 O1_$2 TEMP -123 SIZE 0.116 0.136 0.282 LIST 4 L.S. 10 WGHT 0.038500 0.574900 FVAR 4.37946 N 3 0.526431 0.860695 0.267705 11.00000 0.02096 0.01721 = 0.02330 -0.00291 0.00233 -0.00348 O1 4 0.174800 0.474126 0.277567 11.00000 0.02461 0.01999 = 0.04352 -0.00138 0.00871 0.00142 O2 4 0.107685 0.608878 0.265376 11.00000 0.01890 0.01802 = 0.02715 -0.00002 0.00288 -0.00264 O3 4 0.062995 0.732488 0.121625 11.00000 0.01880 0.03344 = 0.02462 -0.00139 -0.00467 -0.00033 H3A 2 0.013074 0.743999 0.155832 11.00000 0.02941 O4 4 0.032012 0.783237 0.276283 11.00000 0.01995 0.02557 = 0.03034 -0.00428 0.00041 0.00219 O5 4 0.239494 0.837301 0.375300 11.00000 0.02882 0.01944 = 0.02490 -0.00652 -0.00283 0.00018 H5A 2 0.259030 0.820022 0.424304 11.00000 0.04186 O6 4 0.294625 0.624289 0.380653 11.00000 0.02197 0.01793 = 0.02046 0.00253 0.00136 -0.00243 O7 4 0.294445 0.712171 0.497375 11.00000 0.03986 0.02808 = 0.02242 -0.00117 -0.00161 -0.00268 O8 4 0.567331 0.653643 0.370399 11.00000 0.02611 0.02674 = 0.02763 0.00695 -0.00587 -0.00073 O9 4 0.732472 0.603912 0.195036 11.00000 0.02733 0.02297 = 0.03749 -0.00585 -0.00811 0.00800 O10 4 0.777316 0.810285 0.123530 11.00000 0.02045 0.02643 = 0.03314 -0.00401 0.00540 -0.00548 H10A 2 0.777040 0.859027 0.153586 11.00000 0.05640 O11 4 0.410973 0.865638 0.073907 11.00000 0.02557 0.01920 = 0.02409 0.00325 0.00376 0.00387 C1 1 0.112940 0.529161 0.300092 11.00000 0.01827 0.01654 = 0.02862 -0.00239 -0.00139 -0.00279 C2 1 0.031220 0.519816 0.367623 11.00000 0.01763 0.02246 = 0.02514 -0.00157 -0.00132 -0.00233 C3 1 -0.030161 0.590839 0.392359 11.00000 0.02929 0.02291 = 0.02630 -0.00278 0.00190 -0.00102 AFIX 43 H3 2 -0.018625 0.646269 0.367087 11.00000 -1.20000 AFIX 0 C4 1 -0.107800 0.580236 0.453764 11.00000 0.03343 0.03102 = 0.03009 -0.00750 0.00779 0.00021 AFIX 43 H4 2 -0.149847 0.628516 0.470295 11.00000 -1.20000 AFIX 0 C5 1 -0.124737 0.500029 0.491271 11.00000 0.02727 0.04089 = 0.02546 -0.00396 0.00450 -0.00902 AFIX 43 H5 2 -0.177592 0.493384 0.533977 11.00000 -1.20000 AFIX 0 C6 1 -0.064650 0.429577 0.466525 11.00000 0.02838 0.03220 = 0.04194 0.01076 0.00248 -0.00567 AFIX 43 H6 2 -0.076965 0.374239 0.491749 11.00000 -1.20000 AFIX 0 C7 1 0.013528 0.439045 0.405119 11.00000 0.02263 0.02374 = 0.04574 0.00491 0.00464 0.00007 AFIX 43 H7 2 0.054997 0.390404 0.388652 11.00000 -1.20000 AFIX 0 C8 1 0.181918 0.635519 0.200929 11.00000 0.01897 0.02014 = 0.02011 -0.00264 0.00196 -0.00274 AFIX 13 H8 2 0.178608 0.595559 0.150284 11.00000 -1.20000 AFIX 0 C9 1 0.154185 0.727853 0.174046 11.00000 0.01885 0.02183 = 0.02158 -0.00052 -0.00302 -0.00166 C10 1 0.141395 0.786368 0.254110 11.00000 0.02039 0.01872 = 0.02353 -0.00093 -0.00028 0.00009 AFIX 13 H10 2 0.159914 0.847438 0.237998 11.00000 -1.20000 AFIX 0 C11 1 -0.002057 0.848820 0.334014 11.00000 0.02908 0.03578 = 0.04169 -0.01045 0.00138 0.00834 AFIX 137 H11A 2 0.019887 0.905894 0.312453 11.00000 -1.50000 H11B 2 0.029358 0.838768 0.390690 11.00000 -1.50000 H11C 2 -0.078960 0.847122 0.338798 11.00000 -1.50000 AFIX 0 C12 1 0.208498 0.759414 0.332839 11.00000 0.02076 0.01738 = 0.02129 -0.00267 0.00032 -0.00114 AFIX 13 H12 2 0.159729 0.728545 0.373034 11.00000 -1.20000 AFIX 0 C13 1 0.303080 0.696243 0.316802 11.00000 0.01970 0.01639 = 0.01757 0.00127 0.00027 -0.00098 C14 1 0.292591 0.640823 0.465599 11.00000 0.02349 0.02611 = 0.02105 0.00225 0.00013 -0.00247 C15 1 0.286136 0.557517 0.515385 11.00000 0.05651 0.02976 = 0.02649 0.00689 0.00077 -0.00592 AFIX 137 H15A 2 0.227525 0.522423 0.493590 11.00000 -1.50000 H15B 2 0.274573 0.570540 0.576327 11.00000 -1.50000 H15C 2 0.352091 0.525130 0.508783 11.00000 -1.50000 AFIX 0 C16 1 0.295281 0.645862 0.231156 11.00000 0.01861 0.01586 = 0.02054 -0.00186 0.00142 -0.00274 AFIX 13 H16 2 0.329692 0.587641 0.236715 11.00000 -1.20000 AFIX 0 C17 1 0.345500 0.697999 0.155463 11.00000 0.01968 0.01855 = 0.01820 -0.00146 0.00141 -0.00262 AFIX 13 H17 2 0.361991 0.655016 0.109139 11.00000 -1.20000 AFIX 0 C18 1 0.251480 0.754529 0.122330 11.00000 0.02089 0.02588 = 0.02069 0.00289 -0.00183 -0.00192 AFIX 23 H18A 2 0.266657 0.817082 0.130896 11.00000 -1.20000 H18B 2 0.239678 0.744101 0.060272 11.00000 -1.20000 AFIX 0 C19 1 0.449611 0.748660 0.174657 11.00000 0.01763 0.01601 = 0.01938 0.00031 0.00130 -0.00206 C20 1 0.433442 0.806257 0.253936 11.00000 0.01912 0.01659 = 0.01968 -0.00082 0.00131 -0.00165 AFIX 13 H20 2 0.369370 0.843324 0.246656 11.00000 -1.20000 AFIX 0 C21 1 0.413772 0.735399 0.323361 11.00000 0.02023 0.01675 = 0.01844 -0.00043 -0.00060 -0.00246 AFIX 13 H21 2 0.426733 0.759087 0.382286 11.00000 -1.20000 AFIX 0 C22 1 0.494335 0.662500 0.301441 11.00000 0.01880 0.01861 = 0.02311 0.00145 -0.00082 -0.00195 AFIX 13 H22 2 0.455000 0.606484 0.295524 11.00000 -1.20000 AFIX 0 C23 1 0.589409 0.565669 0.390461 11.00000 0.03345 0.03917 = 0.06247 0.02560 -0.00975 -0.00100 AFIX 137 H23A 2 0.523436 0.534921 0.402426 11.00000 -1.50000 H23B 2 0.635052 0.563082 0.441189 11.00000 -1.50000 H23C 2 0.625016 0.538132 0.341650 11.00000 -1.50000 AFIX 0 C24 1 0.538630 0.688155 0.210549 11.00000 0.01799 0.01595 = 0.02182 -0.00028 0.00000 -0.00091 AFIX 13 H24 2 0.547046 0.635452 0.173517 11.00000 -1.20000 AFIX 0 C25 1 0.643800 0.739151 0.216710 11.00000 0.01804 0.01909 = 0.02267 -0.00217 0.00011 -0.00210 C26 1 0.734111 0.680519 0.247090 11.00000 0.02084 0.02244 = 0.02842 -0.00144 -0.00157 -0.00150 AFIX 23 H26A 2 0.802337 0.710973 0.240726 11.00000 -1.20000 H26B 2 0.724527 0.665065 0.308373 11.00000 -1.20000 AFIX 0 C27 1 0.814768 0.545945 0.215333 11.00000 0.03267 0.03107 = 0.03789 -0.00069 -0.00586 0.01065 AFIX 137 H27A 2 0.809832 0.494380 0.178528 11.00000 -1.50000 H27B 2 0.809051 0.528455 0.275733 11.00000 -1.50000 H27C 2 0.882637 0.574698 0.205848 11.00000 -1.50000 AFIX 0 C28 1 0.627533 0.815020 0.280227 11.00000 0.01950 0.02142 = 0.02325 -0.00218 0.00024 -0.00428 AFIX 23 H28A 2 0.630504 0.792189 0.339683 11.00000 -1.20000 H28B 2 0.685850 0.857158 0.273306 11.00000 -1.20000 AFIX 0 C29 1 0.511279 0.925552 0.334534 11.00000 0.02886 0.02128 = 0.03095 -0.00775 0.00265 -0.00335 AFIX 137 H29A 2 0.568909 0.967875 0.332471 11.00000 -1.50000 H29B 2 0.510595 0.897007 0.390858 11.00000 -1.50000 H29C 2 0.444116 0.955506 0.325336 11.00000 -1.50000 AFIX 0 C30 1 0.674371 0.771618 0.125935 11.00000 0.01798 0.02069 = 0.02431 -0.00372 0.00336 -0.00384 AFIX 13 H30 2 0.676224 0.719561 0.087435 11.00000 -1.20000 AFIX 0 C31 1 0.593999 0.833377 0.089323 11.00000 0.02255 0.01993 = 0.02236 0.00100 0.00409 -0.00307 AFIX 23 H31A 2 0.613325 0.847469 0.029263 11.00000 -1.20000 H31B 2 0.595220 0.888133 0.122784 11.00000 -1.20000 AFIX 0 C32 1 0.482722 0.795978 0.090849 11.00000 0.02113 0.01631 = 0.02003 0.00019 0.00155 0.00143 AFIX 13 H32 2 0.476840 0.753374 0.042518 11.00000 -1.20000 AFIX 0 C33 1 0.395378 0.881584 -0.014904 11.00000 0.03035 0.03071 = 0.02587 0.00451 -0.00226 0.00605 AFIX 137 H33A 2 0.461393 0.901873 -0.040612 11.00000 -1.50000 H33B 2 0.340957 0.926145 -0.022254 11.00000 -1.50000 H33C 2 0.372997 0.827762 -0.043266 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)2(1)2(1) REM wR2 = 0.0683, GooF = S = 1.039, Restrained GooF = 1.039 for all data REM R1 = 0.0268 for 5983 Fo > 4sig(Fo) and 0.0271 for all 6062 data REM 424 parameters refined using 0 restraints END WGHT 0.0385 0.5749 REM Highest difference peak 0.182, deepest hole -0.168, 1-sigma level 0.039 Q1 1 0.3991 0.7220 0.1698 11.00000 0.05 0.18 Q2 1 0.5547 0.6018 0.4357 11.00000 0.05 0.18 Q3 1 0.5414 0.8140 0.0929 11.00000 0.05 0.18 Q4 1 0.2880 0.5040 0.4811 11.00000 0.05 0.17 Q5 1 0.3590 0.7182 0.3193 11.00000 0.05 0.16 ; _shelx_res_checksum 49677 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 N N 0.52643(11) 0.86069(9) 0.26770(9) 0.0205(3) Uani 1 1 d . . . . . O1 O 0.17480(10) 0.47413(8) 0.27757(10) 0.0294(3) Uani 1 1 d . . . . . O2 O 0.10769(9) 0.60888(7) 0.26538(8) 0.0214(2) Uani 1 1 d . . . . . O3 O 0.06300(10) 0.73249(9) 0.12162(8) 0.0256(3) Uani 1 1 d . . . . . H3A H 0.013(2) 0.7440(15) 0.1558(15) 0.029(6) Uiso 1 1 d . . . . . O4 O 0.03201(10) 0.78324(8) 0.27628(8) 0.0253(3) Uani 1 1 d . . . . . O5 O 0.23949(11) 0.83730(8) 0.37530(9) 0.0244(3) Uani 1 1 d . . . . . H5A H 0.259(2) 0.8200(18) 0.4243(18) 0.042(7) Uiso 1 1 d . . . . . O6 O 0.29463(9) 0.62429(7) 0.38065(7) 0.0201(2) Uani 1 1 d . . . . . O7 O 0.29445(12) 0.71217(9) 0.49738(8) 0.0301(3) Uani 1 1 d . . . . . O8 O 0.56733(10) 0.65364(8) 0.37040(8) 0.0268(3) Uani 1 1 d . . . . . O9 O 0.73247(10) 0.60391(8) 0.19504(9) 0.0293(3) Uani 1 1 d . . . . . O10 O 0.77732(10) 0.81028(9) 0.12353(9) 0.0267(3) Uani 1 1 d . . . . . H10A H 0.777(2) 0.859(2) 0.154(2) 0.056(9) Uiso 1 1 d . . . . . O11 O 0.41097(10) 0.86564(8) 0.07391(8) 0.0230(3) Uani 1 1 d . . . . . C1 C 0.11294(13) 0.52916(11) 0.30009(12) 0.0211(3) Uani 1 1 d . . . . . C2 C 0.03122(13) 0.51982(11) 0.36762(12) 0.0217(3) Uani 1 1 d . . . . . C3 C -0.03016(15) 0.59084(12) 0.39236(12) 0.0262(4) Uani 1 1 d . . . . . H3 H -0.018625 0.646269 0.367087 0.031 Uiso 1 1 calc R U . . . C4 C -0.10780(16) 0.58024(14) 0.45376(13) 0.0315(4) Uani 1 1 d . . . . . H4 H -0.149847 0.628516 0.470295 0.038 Uiso 1 1 calc R U . . . C5 C -0.12474(16) 0.50003(14) 0.49127(13) 0.0312(4) Uani 1 1 d . . . . . H5 H -0.177592 0.493384 0.533977 0.037 Uiso 1 1 calc R U . . . C6 C -0.06465(16) 0.42958(14) 0.46652(14) 0.0342(4) Uani 1 1 d . . . . . H6 H -0.076965 0.374239 0.491749 0.041 Uiso 1 1 calc R U . . . C7 C 0.01353(15) 0.43905(13) 0.40512(14) 0.0307(4) Uani 1 1 d . . . . . H7 H 0.054997 0.390404 0.388652 0.037 Uiso 1 1 calc R U . . . C8 C 0.18192(13) 0.63552(11) 0.20093(10) 0.0197(3) Uani 1 1 d . . . . . H8 H 0.178608 0.595559 0.150284 0.024 Uiso 1 1 calc R U . . . C9 C 0.15419(13) 0.72785(11) 0.17405(11) 0.0208(3) Uani 1 1 d . . . . . C10 C 0.14139(13) 0.78637(11) 0.25411(11) 0.0209(3) Uani 1 1 d . . . . . H10 H 0.159914 0.847438 0.237998 0.025 Uiso 1 1 calc R U . . . C11 C -0.00206(17) 0.84882(14) 0.33401(14) 0.0355(5) Uani 1 1 d . . . . . H11A H 0.019887 0.905894 0.312453 0.053 Uiso 1 1 calc R U . . . H11B H 0.029358 0.838768 0.390690 0.053 Uiso 1 1 calc R U . . . H11C H -0.078960 0.847122 0.338798 0.053 Uiso 1 1 calc R U . . . C12 C 0.20850(13) 0.75941(11) 0.33284(11) 0.0198(3) Uani 1 1 d . . . . . H12 H 0.159729 0.728545 0.373034 0.024 Uiso 1 1 calc R U . . . C13 C 0.30308(13) 0.69624(10) 0.31680(10) 0.0179(3) Uani 1 1 d . . . . . C14 C 0.29259(14) 0.64082(12) 0.46560(11) 0.0235(4) Uani 1 1 d . . . . . C15 C 0.2861(2) 0.55752(14) 0.51538(13) 0.0376(5) Uani 1 1 d . . . . . H15A H 0.227525 0.522423 0.493590 0.056 Uiso 1 1 calc R U . . . H15B H 0.274573 0.570540 0.576327 0.056 Uiso 1 1 calc R U . . . H15C H 0.352091 0.525130 0.508783 0.056 Uiso 1 1 calc R U . . . C16 C 0.29528(13) 0.64586(10) 0.23116(10) 0.0183(3) Uani 1 1 d . . . . . H16 H 0.329692 0.587641 0.236715 0.022 Uiso 1 1 calc R U . . . C17 C 0.34550(13) 0.69800(11) 0.15546(10) 0.0188(3) Uani 1 1 d . . . . . H17 H 0.361991 0.655016 0.109139 0.023 Uiso 1 1 calc R U . . . C18 C 0.25148(13) 0.75453(11) 0.12233(11) 0.0225(3) Uani 1 1 d . . . . . H18A H 0.266657 0.817082 0.130896 0.027 Uiso 1 1 calc R U . . . H18B H 0.239678 0.744101 0.060272 0.027 Uiso 1 1 calc R U . . . C19 C 0.44961(12) 0.74866(10) 0.17466(10) 0.0177(3) Uani 1 1 d . . . . . C20 C 0.43344(13) 0.80626(11) 0.25394(11) 0.0185(3) Uani 1 1 d . . . . . H20 H 0.369370 0.843324 0.246656 0.022 Uiso 1 1 calc R U . . . C21 C 0.41377(13) 0.73540(10) 0.32336(10) 0.0185(3) Uani 1 1 d . . . . . H21 H 0.426733 0.759087 0.382286 0.022 Uiso 1 1 calc R U . . . C22 C 0.49433(13) 0.66250(11) 0.30144(11) 0.0202(3) Uani 1 1 d . . . . . H22 H 0.455000 0.606484 0.295524 0.024 Uiso 1 1 calc R U . . . C23 C 0.58941(18) 0.56567(15) 0.39046(18) 0.0450(6) Uani 1 1 d . . . . . H23A H 0.523436 0.534921 0.402426 0.068 Uiso 1 1 calc R U . . . H23B H 0.635052 0.563082 0.441189 0.068 Uiso 1 1 calc R U . . . H23C H 0.625016 0.538132 0.341650 0.068 Uiso 1 1 calc R U . . . C24 C 0.53863(13) 0.68815(11) 0.21055(11) 0.0186(3) Uani 1 1 d . . . . . H24 H 0.547046 0.635452 0.173517 0.022 Uiso 1 1 calc R U . . . C25 C 0.64380(13) 0.73915(11) 0.21671(11) 0.0199(3) Uani 1 1 d . . . . . C26 C 0.73411(14) 0.68052(11) 0.24709(12) 0.0239(4) Uani 1 1 d . . . . . H26A H 0.802337 0.710973 0.240726 0.029 Uiso 1 1 calc R U . . . H26B H 0.724527 0.665065 0.308373 0.029 Uiso 1 1 calc R U . . . C27 C 0.81477(16) 0.54594(13) 0.21533(14) 0.0339(4) Uani 1 1 d . . . . . H27A H 0.809832 0.494380 0.178528 0.051 Uiso 1 1 calc R U . . . H27B H 0.809051 0.528455 0.275733 0.051 Uiso 1 1 calc R U . . . H27C H 0.882637 0.574698 0.205848 0.051 Uiso 1 1 calc R U . . . C28 C 0.62753(13) 0.81502(11) 0.28023(11) 0.0214(3) Uani 1 1 d . . . . . H28A H 0.630504 0.792189 0.339683 0.026 Uiso 1 1 calc R U . . . H28B H 0.685850 0.857158 0.273306 0.026 Uiso 1 1 calc R U . . . C29 C 0.51128(15) 0.92555(12) 0.33453(12) 0.0270(4) Uani 1 1 d . . . . . H29A H 0.568909 0.967875 0.332471 0.041 Uiso 1 1 calc R U . . . H29B H 0.510595 0.897007 0.390858 0.041 Uiso 1 1 calc R U . . . H29C H 0.444116 0.955506 0.325336 0.041 Uiso 1 1 calc R U . . . C30 C 0.67437(13) 0.77162(11) 0.12594(11) 0.0210(3) Uani 1 1 d . . . . . H30 H 0.676224 0.719561 0.087435 0.025 Uiso 1 1 calc R U . . . C31 C 0.59400(13) 0.83338(11) 0.08932(11) 0.0216(3) Uani 1 1 d . . . . . H31A H 0.613325 0.847469 0.029263 0.026 Uiso 1 1 calc R U . . . H31B H 0.595220 0.888133 0.122784 0.026 Uiso 1 1 calc R U . . . C32 C 0.48272(13) 0.79598(10) 0.09085(11) 0.0192(3) Uani 1 1 d . . . . . H32 H 0.476840 0.753374 0.042518 0.023 Uiso 1 1 calc R U . . . C33 C 0.39538(16) 0.88158(13) -0.01490(12) 0.0290(4) Uani 1 1 d . . . . . H33A H 0.461393 0.901873 -0.040612 0.043 Uiso 1 1 calc R U . . . H33B H 0.340957 0.926145 -0.022254 0.043 Uiso 1 1 calc R U . . . H33C H 0.372997 0.827762 -0.043266 0.043 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 N 0.0210(7) 0.0172(7) 0.0233(7) -0.0029(5) 0.0023(5) -0.0035(5) O1 0.0246(6) 0.0200(6) 0.0435(8) -0.0014(5) 0.0087(6) 0.0014(5) O2 0.0189(6) 0.0180(6) 0.0272(6) 0.0000(5) 0.0029(5) -0.0026(5) O3 0.0188(6) 0.0334(7) 0.0246(6) -0.0014(5) -0.0047(5) -0.0003(5) O4 0.0199(6) 0.0256(6) 0.0303(6) -0.0043(5) 0.0004(5) 0.0022(5) O5 0.0288(6) 0.0194(6) 0.0249(6) -0.0065(5) -0.0028(5) 0.0002(5) O6 0.0220(5) 0.0179(5) 0.0205(5) 0.0025(5) 0.0014(4) -0.0024(5) O7 0.0399(8) 0.0281(7) 0.0224(6) -0.0012(5) -0.0016(6) -0.0027(6) O8 0.0261(6) 0.0267(6) 0.0276(6) 0.0069(5) -0.0059(5) -0.0007(5) O9 0.0273(7) 0.0230(6) 0.0375(7) -0.0058(5) -0.0081(6) 0.0080(5) O10 0.0205(6) 0.0264(6) 0.0331(7) -0.0040(6) 0.0054(5) -0.0055(5) O11 0.0256(6) 0.0192(6) 0.0241(6) 0.0032(5) 0.0038(5) 0.0039(5) C1 0.0183(7) 0.0165(8) 0.0286(9) -0.0024(6) -0.0014(7) -0.0028(6) C2 0.0176(7) 0.0225(8) 0.0251(8) -0.0016(7) -0.0013(7) -0.0023(6) C3 0.0293(9) 0.0229(9) 0.0263(9) -0.0028(7) 0.0019(7) -0.0010(7) C4 0.0334(10) 0.0310(10) 0.0301(10) -0.0075(8) 0.0078(8) 0.0002(8) C5 0.0273(9) 0.0409(11) 0.0255(9) -0.0040(8) 0.0045(8) -0.0090(8) C6 0.0284(9) 0.0322(10) 0.0419(11) 0.0108(9) 0.0025(8) -0.0057(8) C7 0.0226(8) 0.0237(9) 0.0457(11) 0.0049(8) 0.0046(8) 0.0001(7) C8 0.0190(8) 0.0201(8) 0.0201(8) -0.0026(6) 0.0020(6) -0.0027(6) C9 0.0188(8) 0.0218(8) 0.0216(8) -0.0005(7) -0.0030(6) -0.0017(7) C10 0.0204(8) 0.0187(8) 0.0235(8) -0.0009(6) -0.0003(6) 0.0001(6) C11 0.0291(10) 0.0358(11) 0.0417(11) -0.0104(9) 0.0014(8) 0.0083(8) C12 0.0208(8) 0.0174(8) 0.0213(8) -0.0027(6) 0.0003(6) -0.0011(6) C13 0.0197(8) 0.0164(7) 0.0176(7) 0.0013(6) 0.0003(6) -0.0010(6) C14 0.0235(8) 0.0261(9) 0.0210(8) 0.0022(7) 0.0001(7) -0.0025(7) C15 0.0565(14) 0.0298(10) 0.0265(9) 0.0069(8) 0.0008(9) -0.0059(10) C16 0.0186(7) 0.0159(7) 0.0205(8) -0.0019(6) 0.0014(6) -0.0027(6) C17 0.0197(8) 0.0186(8) 0.0182(7) -0.0015(6) 0.0014(6) -0.0026(6) C18 0.0209(8) 0.0259(8) 0.0207(8) 0.0029(7) -0.0018(6) -0.0019(7) C19 0.0176(7) 0.0160(7) 0.0194(8) 0.0003(6) 0.0013(6) -0.0021(6) C20 0.0191(7) 0.0166(7) 0.0197(7) -0.0008(6) 0.0013(6) -0.0017(6) C21 0.0202(7) 0.0168(7) 0.0184(7) -0.0004(6) -0.0006(6) -0.0025(6) C22 0.0188(7) 0.0186(8) 0.0231(8) 0.0014(6) -0.0008(6) -0.0019(6) C23 0.0334(11) 0.0392(12) 0.0625(15) 0.0256(11) -0.0097(10) -0.0010(9) C24 0.0180(7) 0.0160(7) 0.0218(8) -0.0003(6) 0.0000(6) -0.0009(6) C25 0.0180(7) 0.0191(8) 0.0227(8) -0.0022(7) 0.0001(6) -0.0021(6) C26 0.0208(8) 0.0224(8) 0.0284(9) -0.0014(7) -0.0016(7) -0.0015(7) C27 0.0327(10) 0.0311(10) 0.0379(10) -0.0007(8) -0.0059(8) 0.0107(8) C28 0.0195(8) 0.0214(8) 0.0232(8) -0.0022(7) 0.0002(6) -0.0043(6) C29 0.0289(9) 0.0213(9) 0.0309(9) -0.0077(7) 0.0026(7) -0.0033(7) C30 0.0180(7) 0.0207(8) 0.0243(8) -0.0037(7) 0.0034(6) -0.0038(6) C31 0.0226(8) 0.0199(8) 0.0224(8) 0.0010(6) 0.0041(6) -0.0031(7) C32 0.0211(8) 0.0163(8) 0.0200(7) 0.0002(6) 0.0015(6) 0.0014(6) C33 0.0304(9) 0.0307(10) 0.0259(9) 0.0045(7) -0.0023(7) 0.0060(8) 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' N N 0.0311 0.0180 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 9 4 0.1134 8 -1 2 0.0274 -8 0 -2 0.0777 -3 -8 -4 0.1545 8 -3 1 0.0477 6 0 -7 0.0375 1 9 5 0.0999 -6 -2 7 0.0725 -6 0 7 0.0782 1 -1 -10 0.0569 2 7 -7 0.0800 -1 0 10 0.0744 -1 -8 6 0.1030 7 0 6 0.0316 -7 1 5 0.0777 -4 6 -6 0.1104 4 -7 5 0.0827 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 C29 N C20 112.97(14) . . ? C29 N C28 110.31(14) . . ? C20 N C28 116.69(13) . . ? C1 O2 C8 120.61(13) . . ? C9 O3 H3A 105.1(16) . . ? C11 O4 C10 115.13(14) . . ? C12 O5 H5A 103.6(18) . . ? C14 O6 C13 121.02(13) . . ? C23 O8 C22 112.72(15) . . ? C27 O9 C26 112.54(15) . . ? C30 O10 H10A 109(2) . . ? C33 O11 C32 113.46(13) . . ? O1 C1 O2 123.81(16) . . ? O1 C1 C2 126.38(16) . . ? O2 C1 C2 109.80(14) . . ? C7 C2 C3 119.53(17) . . ? C7 C2 C1 119.77(16) . . ? C3 C2 C1 120.67(16) . . ? C4 C3 C2 119.77(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.55(19) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 119.80(18) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.41(18) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 119.93(18) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? O2 C8 C9 107.82(13) . . ? O2 C8 C16 115.79(13) . . ? C9 C8 C16 101.91(13) . . ? O2 C8 H8 110.3 . . ? C9 C8 H8 110.3 . . ? C16 C8 H8 110.3 . . ? O3 C9 C8 113.20(14) . . ? O3 C9 C18 110.10(13) . . ? C8 C9 C18 101.98(13) . . ? O3 C9 C10 110.39(14) . . ? C8 C9 C10 110.26(13) . . ? C18 C9 C10 110.64(14) . . ? O4 C10 C9 106.05(13) . . ? O4 C10 C12 109.54(14) . . ? C9 C10 C12 115.07(14) . . ? O4 C10 H10 108.7 . . ? C9 C10 H10 108.7 . . ? C12 C10 H10 108.7 . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O5 C12 C10 107.10(13) . . ? O5 C12 C13 112.58(13) . . ? C10 C12 C13 117.55(13) . . ? O5 C12 H12 106.3 . . ? C10 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? O6 C13 C21 108.26(12) . . ? O6 C13 C16 101.41(12) . . ? C21 C13 C16 108.26(13) . . ? O6 C13 C12 107.41(12) . . ? C21 C13 C12 116.73(13) . . ? C16 C13 C12 113.56(13) . . ? O7 C14 O6 125.10(16) . . ? O7 C14 C15 124.60(17) . . ? O6 C14 C15 110.29(16) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 C13 112.29(13) . . ? C8 C16 C17 101.95(13) . . ? C13 C16 C17 111.53(12) . . ? C8 C16 H16 110.3 . . ? C13 C16 H16 110.3 . . ? C17 C16 H16 110.3 . . ? C16 C17 C19 117.23(13) . . ? C16 C17 C18 102.82(13) . . ? C19 C17 C18 115.58(13) . . ? C16 C17 H17 106.8 . . ? C19 C17 H17 106.8 . . ? C18 C17 H17 106.8 . . ? C9 C18 C17 107.11(13) . . ? C9 C18 H18A 110.3 . . ? C17 C18 H18A 110.3 . . ? C9 C18 H18B 110.3 . . ? C17 C18 H18B 110.3 . . ? H18A C18 H18B 108.5 . . ? C20 C19 C32 116.21(13) . . ? C20 C19 C17 109.17(13) . . ? C32 C19 C17 107.61(13) . . ? C20 C19 C24 98.81(12) . . ? C32 C19 C24 112.48(13) . . ? C17 C19 C24 112.49(13) . . ? N C20 C19 109.89(13) . . ? N C20 C21 115.40(14) . . ? C19 C20 C21 100.11(12) . . ? N C20 H20 110.3 . . ? C19 C20 H20 110.3 . . ? C21 C20 H20 110.3 . . ? C13 C21 C20 112.12(13) . . ? C13 C21 C22 107.80(13) . . ? C20 C21 C22 104.31(13) . . ? C13 C21 H21 110.8 . . ? C20 C21 H21 110.8 . . ? C22 C21 H21 110.8 . . ? O8 C22 C21 109.39(13) . . ? O8 C22 C24 117.93(13) . . ? C21 C22 C24 104.58(13) . . ? O8 C22 H22 108.2 . . ? C21 C22 H22 108.2 . . ? C24 C22 H22 108.2 . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C19 110.07(13) . . ? C25 C24 C22 112.29(13) . . ? C19 C24 C22 102.19(12) . . ? C25 C24 H24 110.7 . . ? C19 C24 H24 110.7 . . ? C22 C24 H24 110.7 . . ? C26 C25 C28 110.33(14) . . ? C26 C25 C30 106.45(14) . . ? C28 C25 C30 111.97(14) . . ? C26 C25 C24 111.46(13) . . ? C28 C25 C24 107.84(13) . . ? C30 C25 C24 108.83(13) . . ? O9 C26 C25 107.40(14) . . ? O9 C26 H26A 110.2 . . ? C25 C26 H26A 110.2 . . ? O9 C26 H26B 110.2 . . ? C25 C26 H26B 110.2 . . ? H26A C26 H26B 108.5 . . ? O9 C27 H27A 109.5 . . ? O9 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O9 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N C28 C25 113.06(13) . . ? N C28 H28A 109.0 . . ? C25 C28 H28A 109.0 . . ? N C28 H28B 109.0 . . ? C25 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? N C29 H29A 109.5 . . ? N C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O10 C30 C31 110.25(14) . . ? O10 C30 C25 112.68(14) . . ? C31 C30 C25 112.24(13) . . ? O10 C30 H30 107.1 . . ? C31 C30 H30 107.1 . . ? C25 C30 H30 107.1 . . ? C30 C31 C32 112.60(13) . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? O11 C32 C31 107.75(13) . . ? O11 C32 C19 109.47(13) . . ? C31 C32 C19 116.17(14) . . ? O11 C32 H32 107.7 . . ? C31 C32 H32 107.7 . . ? C19 C32 H32 107.7 . . ? O11 C33 H33A 109.5 . . ? O11 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O11 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 N C29 1.453(2) . ? N C20 1.463(2) . ? N C28 1.477(2) . ? O1 C1 1.207(2) . ? O2 C1 1.341(2) . ? O2 C8 1.436(2) . ? O3 C9 1.418(2) . ? O3 H3A 0.85(3) . ? O4 C11 1.418(2) . ? O4 C10 1.432(2) . ? O5 C12 1.423(2) . ? O5 H5A 0.84(3) . ? O6 C14 1.346(2) . ? O6 C13 1.4907(19) . ? O7 C14 1.204(2) . ? O8 C23 1.416(2) . ? O8 C22 1.424(2) . ? O9 C27 1.410(2) . ? O9 C26 1.430(2) . ? O10 C30 1.4369(19) . ? O10 H10A 0.88(3) . ? O11 C33 1.417(2) . ? O11 C32 1.431(2) . ? C1 C2 1.484(2) . ? C2 C7 1.390(3) . ? C2 C3 1.396(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.521(2) . ? C8 C16 1.523(2) . ? C8 H8 1.0000 . ? C9 C18 1.531(2) . ? C9 C10 1.545(2) . ? C10 C12 1.549(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.565(2) . ? C12 H12 1.0000 . ? C13 C21 1.533(2) . ? C13 C16 1.544(2) . ? C14 C15 1.499(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.561(2) . ? C16 H16 1.0000 . ? C17 C19 1.564(2) . ? C17 C18 1.564(2) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.532(2) . ? C19 C32 1.551(2) . ? C19 C24 1.567(2) . ? C20 C21 1.554(2) . ? C20 H20 1.0000 . ? C21 C22 1.556(2) . ? C21 H21 1.0000 . ? C22 C24 1.572(2) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.552(2) . ? C24 H24 1.0000 . ? C25 C26 1.534(2) . ? C25 C28 1.543(2) . ? C25 C30 1.547(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.506(2) . ? C30 H30 1.0000 . ? C31 C32 1.526(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 _geom_hbond_publ_flag O3 H3A O4 0.85(3) 1.98(2) 2.5597(18) 125(2) . yes O5 H5A O7 0.84(3) 2.06(3) 2.7920(19) 145(2) . yes O10 H10A O1 0.88(3) 2.16(3) 3.0140(19) 163(3) 3_655 yes 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 C8 O2 C1 O1 -3.8(2) . . . . ? C8 O2 C1 C2 177.17(13) . . . . ? O1 C1 C2 C7 -6.8(3) . . . . ? O2 C1 C2 C7 172.18(16) . . . . ? O1 C1 C2 C3 174.92(18) . . . . ? O2 C1 C2 C3 -6.1(2) . . . . ? C7 C2 C3 C4 0.0(3) . . . . ? C1 C2 C3 C4 178.27(17) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C2 -0.5(3) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C1 C2 C7 C6 -178.25(18) . . . . ? C1 O2 C8 C9 179.24(14) . . . . ? C1 O2 C8 C16 -67.43(19) . . . . ? O2 C8 C9 O3 -74.00(16) . . . . ? C16 C8 C9 O3 163.66(13) . . . . ? O2 C8 C9 C18 167.75(13) . . . . ? C16 C8 C9 C18 45.42(15) . . . . ? O2 C8 C9 C10 50.20(17) . . . . ? C16 C8 C9 C10 -72.13(16) . . . . ? C11 O4 C10 C9 -164.73(15) . . . . ? C11 O4 C10 C12 70.52(19) . . . . ? O3 C9 C10 O4 33.83(18) . . . . ? C8 C9 C10 O4 -91.99(15) . . . . ? C18 C9 C10 O4 155.96(14) . . . . ? O3 C9 C10 C12 155.08(14) . . . . ? C8 C9 C10 C12 29.27(19) . . . . ? C18 C9 C10 C12 -82.79(18) . . . . ? O4 C10 C12 O5 -95.51(15) . . . . ? C9 C10 C12 O5 145.15(14) . . . . ? O4 C10 C12 C13 136.64(14) . . . . ? C9 C10 C12 C13 17.3(2) . . . . ? C14 O6 C13 C21 69.62(18) . . . . ? C14 O6 C13 C16 -176.60(14) . . . . ? C14 O6 C13 C12 -57.23(18) . . . . ? O5 C12 C13 O6 104.49(15) . . . . ? C10 C12 C13 O6 -130.33(14) . . . . ? O5 C12 C13 C21 -17.21(19) . . . . ? C10 C12 C13 C21 107.97(16) . . . . ? O5 C12 C13 C16 -144.24(14) . . . . ? C10 C12 C13 C16 -19.1(2) . . . . ? C13 O6 C14 O7 2.0(3) . . . . ? C13 O6 C14 C15 -178.78(15) . . . . ? O2 C8 C16 C13 -45.68(19) . . . . ? C9 C8 C16 C13 71.02(16) . . . . ? O2 C8 C16 C17 -165.16(13) . . . . ? C9 C8 C16 C17 -48.46(14) . . . . ? O6 C13 C16 C8 89.05(15) . . . . ? C21 C13 C16 C8 -157.17(13) . . . . ? C12 C13 C16 C8 -25.84(18) . . . . ? O6 C13 C16 C17 -157.22(13) . . . . ? C21 C13 C16 C17 -43.45(17) . . . . ? C12 C13 C16 C17 87.89(16) . . . . ? C8 C16 C17 C19 159.68(14) . . . . ? C13 C16 C17 C19 39.66(19) . . . . ? C8 C16 C17 C18 31.73(15) . . . . ? C13 C16 C17 C18 -88.30(15) . . . . ? O3 C9 C18 C17 -145.49(14) . . . . ? C8 C9 C18 C17 -25.06(16) . . . . ? C10 C9 C18 C17 92.21(16) . . . . ? C16 C17 C18 C9 -4.11(17) . . . . ? C19 C17 C18 C9 -133.10(14) . . . . ? C16 C17 C19 C20 -52.15(18) . . . . ? C18 C17 C19 C20 69.38(17) . . . . ? C16 C17 C19 C32 -179.09(13) . . . . ? C18 C17 C19 C32 -57.56(17) . . . . ? C16 C17 C19 C24 56.47(18) . . . . ? C18 C17 C19 C24 178.00(13) . . . . ? C29 N C20 C19 172.00(14) . . . . ? C28 N C20 C19 -58.56(18) . . . . ? C29 N C20 C21 -75.75(18) . . . . ? C28 N C20 C21 53.68(19) . . . . ? C32 C19 C20 N -52.43(18) . . . . ? C17 C19 C20 N -174.31(13) . . . . ? C24 C19 C20 N 68.07(15) . . . . ? C32 C19 C20 C21 -174.29(13) . . . . ? C17 C19 C20 C21 63.83(15) . . . . ? C24 C19 C20 C21 -53.80(14) . . . . ? O6 C13 C21 C20 175.33(12) . . . . ? C16 C13 C21 C20 66.17(16) . . . . ? C12 C13 C21 C20 -63.42(18) . . . . ? O6 C13 C21 C22 61.09(16) . . . . ? C16 C13 C21 C22 -48.07(16) . . . . ? C12 C13 C21 C22 -177.66(13) . . . . ? N C20 C21 C13 166.34(13) . . . . ? C19 C20 C21 C13 -75.80(15) . . . . ? N C20 C21 C22 -77.28(16) . . . . ? C19 C20 C21 C22 40.58(15) . . . . ? C23 O8 C22 C21 137.55(17) . . . . ? C23 O8 C22 C24 -103.20(19) . . . . ? C13 C21 C22 O8 -124.45(14) . . . . ? C20 C21 C22 O8 116.20(14) . . . . ? C13 C21 C22 C24 108.34(14) . . . . ? C20 C21 C22 C24 -11.00(16) . . . . ? C20 C19 C24 C25 -72.51(15) . . . . ? C32 C19 C24 C25 50.71(17) . . . . ? C17 C19 C24 C25 172.42(13) . . . . ? C20 C19 C24 C22 46.96(14) . . . . ? C32 C19 C24 C22 170.18(13) . . . . ? C17 C19 C24 C22 -68.11(15) . . . . ? O8 C22 C24 C25 -25.8(2) . . . . ? C21 C22 C24 C25 95.97(15) . . . . ? O8 C22 C24 C19 -143.68(14) . . . . ? C21 C22 C24 C19 -21.93(15) . . . . ? C19 C24 C25 C26 -176.96(13) . . . . ? C22 C24 C25 C26 69.91(18) . . . . ? C19 C24 C25 C28 61.80(17) . . . . ? C22 C24 C25 C28 -51.32(17) . . . . ? C19 C24 C25 C30 -59.86(17) . . . . ? C22 C24 C25 C30 -172.99(13) . . . . ? C27 O9 C26 C25 178.04(15) . . . . ? C28 C25 C26 O9 169.58(14) . . . . ? C30 C25 C26 O9 -68.72(16) . . . . ? C24 C25 C26 O9 49.80(18) . . . . ? C29 N C28 C25 174.41(14) . . . . ? C20 N C28 C25 43.72(19) . . . . ? C26 C25 C28 N -165.34(14) . . . . ? C30 C25 C28 N 76.30(17) . . . . ? C24 C25 C28 N -43.40(18) . . . . ? C26 C25 C30 O10 -52.51(17) . . . . ? C28 C25 C30 O10 68.14(17) . . . . ? C24 C25 C30 O10 -172.75(13) . . . . ? C26 C25 C30 C31 -177.68(14) . . . . ? C28 C25 C30 C31 -57.04(18) . . . . ? C24 C25 C30 C31 62.07(17) . . . . ? O10 C30 C31 C32 -179.56(14) . . . . ? C25 C30 C31 C32 -53.05(18) . . . . ? C33 O11 C32 C31 85.25(17) . . . . ? C33 O11 C32 C19 -147.57(14) . . . . ? C30 C31 C32 O11 166.85(14) . . . . ? C30 C31 C32 C19 43.68(19) . . . . ? C20 C19 C32 O11 -52.32(18) . . . . ? C17 C19 C32 O11 70.38(16) . . . . ? C24 C19 C32 O11 -165.17(13) . . . . ? C20 C19 C32 C31 69.96(18) . . . . ? C17 C19 C32 C31 -167.34(13) . . . . ? C24 C19 C32 C31 -42.90(18) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.4325 9.3188 3.5629 0.3117 -0.0735 0.9473 8.0870 -0.7324 1.8489 -0.9373 0.2247 0.2665 -8.0392 -0.3058 -2.2459 0.9026 -0.2165 -0.3720 -3.4976 -8.0742 -4.1107 0.1689 -0.0416 -0.9848 7.7250 -3.4252 0.6906 -0.9721 0.2327 -0.0279 5.5481 -0.1693 -7.4650 -0.7532 -0.6443 -0.1324 1.2731 8.5101 5.0347 0.1136 0.0986 0.9886 -6.0055 -1.5041 6.7485 0.7588 0.6488 -0.0578 -5.6304 -0.0841 7.3737 0.7558 0.6465 0.1038 0.5330 -0.5292 -10.0620 -0.2102 -0.8797 -0.4265 2.3352 6.6367 -6.9787 -0.2154 -0.8980 0.3836 -0.6932 -0.0419 10.0616 0.2158 0.9032 0.3711 -1.0691 -8.0043 5.8871 0.0214 0.8619 -0.5067 6.7373 0.1177 5.8306 -0.7063 0.5420 0.4554 -7.2233 0.6085 4.8283 0.9236 0.3832 0.0136 -4.3604 5.8938 -6.1580 0.5615 -0.8161 0.1369 3.7120 -7.3876 5.0422 -0.5349 0.7765 -0.3332