#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200132.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200132 loop_ _publ_author_name 'Sarkhel, Sanjay' 'Yadava, Umesh' 'Prakash, Prem' 'Jain, Girish K.' 'Singh, Satywan' 'Maulik, Prakash R.' _publ_section_title ; Guggulsterone E, a lipid-lowering agent from Commiphora mukul ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o285 _journal_page_last o286 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C21 H28 O2' _chemical_formula_sum 'C21 H28 O2' _chemical_formula_weight 312.44 _chemical_melting_point 169.0(10) _chemical_name_common 'Guggulsterone E' _chemical_name_systematic ; 4,17(20)-(cis)-pregnadiene-3,16-dione ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00 _cell_angle_beta 94.862(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4634(11) _cell_length_b 13.747(2) _cell_length_c 17.352(3) _cell_measurement_reflns_used 50 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.3 _cell_measurement_theta_min 2.3 _cell_volume 1773.9(5) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics ' NRCVAX (Gabe et al., 1989) and ORTEP (Johnson, 1965)' _computing_publication_material SHELXTL-NT _computing_structure_refinement SHELXTL-NT _computing_structure_solution 'SHELXTL-NT (Bruker, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \q-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0305 _diffrn_reflns_av_sigmaI/netI .0604 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 4388 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.89 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .073 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 680 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _refine_diff_density_max .200 _refine_diff_density_min -.202 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -1(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .921 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 421 _refine_ls_number_reflns 3522 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all .921 _refine_ls_R_factor_all .1106 _refine_ls_R_factor_gt .0633 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1494P)^2^+1.4424P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .2367 _reflns_number_gt 2257 _reflns_number_total 3522 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6049.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '168-170' was changed to '169.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '168-170' was changed to '169.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1773.8(5) _cod_database_code 2200132 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .1816(10) .7886(6) .7295(4) .0565(18) Uani d . 1 . . C H1A .0856 .7895 .6882 .068 Uiso calc R 1 . . H H1B .1541 .7380 .7656 .068 Uiso calc R 1 . . H C2 .1855(11) .8856(6) .7708(4) .063(2) Uani d . 1 . . C H2A .1902 .9374 .7331 .075 Uiso calc R 1 . . H H2B .0753 .8932 .7961 .075 Uiso calc R 1 . . H C3 .3441(13) .8951(6) .8304(4) .071(2) Uani d . 1 . . C C4 .5048(11) .8412(7) .8150(5) .068(2) Uani d . 1 . . C H4 .6047 .8473 .8505 .081 Uiso calc R 1 . . H C5 .5204(8) .7839(6) .7542(4) .0484(16) Uani d . 1 . . C C6 .6961(10) .7412(7) .7382(5) .072(2) Uani d . 1 . . C H6A .7800 .7492 .7836 .086 Uiso calc R 1 . . H H6B .7433 .7767 .6961 .086 Uiso calc R 1 . . H C7 .6847(9) .6335(6) .7172(5) .062(2) Uani d . 1 . . C H7A .6578 .5962 .7622 .074 Uiso calc R 1 . . H H7B .8000 .6118 .7017 .074 Uiso calc R 1 . . H C8 .5387(8) .6148(5) .6509(4) .0428(16) Uani d . 1 . . C H8 .5699 .6494 .6045 .051 Uiso calc R 1 . . H C9 .3583(8) .6532(5) .6749(4) .0391(14) Uani d . 1 . . C H9 .3352 .6183 .7223 .047 Uiso calc R 1 . . H C10 .3575(8) .7631(5) .6953(4) .0422(15) Uani d . 1 . . C C11 .2015(8) .6266(5) .6142(4) .0473(17) Uani d . 1 . . C H11A .0884 .6439 .6344 .057 Uiso calc R 1 . . H H11B .2124 .6647 .5677 .057 Uiso calc R 1 . . H C12 .1980(8) .5186(5) .5932(4) .0490(17) Uani d . 1 . . C H12A .1700 .4810 .6379 .059 Uiso calc R 1 . . H H12B .1034 .5072 .5523 .059 Uiso calc R 1 . . H C13 .3734(8) .4840(5) .5669(4) .0406(15) Uani d . 1 . . C C14 .5201(7) .5081(5) .6333(4) .0407(15) Uani d . 1 . . C H14 .4771 .4789 .6798 .049 Uiso calc R 1 . . H C15 .6806(9) .4463(6) .6148(4) .0559(19) Uani d . 1 . . C H15A .7487 .4776 .5765 .067 Uiso calc R 1 . . H H15B .7598 .4333 .6609 .067 Uiso calc R 1 . . H C16 .5906(11) .3540(6) .5832(4) .060(2) Uani d . 1 . . C C17 .4013(10) .3753(5) .5586(4) .0486(17) Uani d . 1 . . C C18 .2919(12) .3046(6) .5319(4) .061(2) Uani d . 1 . . C H18 .3404 .2422 .5344 .073 Uiso calc R 1 . . H C19 .1031(13) .3116(7) .4985(5) .087(3) Uani d . 1 . . C H19A .0238 .3045 .5390 .130 Uiso calc R 1 . . H H19B .0793 .2611 .4609 .130 Uiso calc R 1 . . H H19C .0838 .3739 .4742 .130 Uiso calc R 1 . . H C20 .3779(13) .8276(6) .6235(4) .075(3) Uani d . 1 . . C H20A .3689 .8949 .6375 .112 Uiso calc R 1 . . H H20B .2845 .8121 .5839 .112 Uiso calc R 1 . . H H20C .4931 .8159 .6044 .112 Uiso calc R 1 . . H C21 .4116(11) .5306(6) .4891(4) .061(2) Uani d . 1 . . C H21A .3417 .4983 .4477 .091 Uiso calc R 1 . . H H21B .5371 .5243 .4818 .091 Uiso calc R 1 . . H H21C .3798 .5983 .4894 .091 Uiso calc R 1 . . H O1 .3400(11) .9490(6) .8865(4) .113(3) Uani d . 1 . . O O2 .6718(9) .2766(5) .5802(4) .0865(19) Uani d . 1 . . O C31 -.0048(10) .2322(6) .7183(4) .0568(19) Uani d . 1 . . C H31A -.1165 .2497 .7396 .068 Uiso calc R 1 . . H H31B .0239 .2836 .6831 .068 Uiso calc R 1 . . H C32 -.0335(10) .1371(6) .6725(5) .064(2) Uani d . 1 . . C H32A -.0776 .0871 .7055 .076 Uiso calc R 1 . . H H32B -.1228 .1471 .6292 .076 Uiso calc R 1 . . H C33 .1420(12) .1047(6) .6430(5) .066(2) Uani d . 1 . . C C34 .3048(11) .1251(6) .6894(5) .062(2) Uani d . 1 . . C H34 .4121 .1011 .6734 .075 Uiso calc R 1 . . H C35 .3106(9) .1770(5) .7550(4) .0525(18) Uani d . 1 . . C C36 .4773(9) .1844(6) .8060(5) .063(2) Uani d . 1 . . C H36A .5743 .1550 .7804 .076 Uiso calc R 1 . . H H36B .4632 .1475 .8527 .076 Uiso calc R 1 . . H C37 .5307(9) .2899(7) .8288(4) .060(2) Uani d . 1 . . C H37A .6353 .2894 .8660 .072 Uiso calc R 1 . . H H37B .5612 .3255 .7834 .072 Uiso calc R 1 . . H C38 .3728(8) .3396(5) .8641(4) .0475(17) Uani d . 1 . . C H38 .3515 .3072 .9128 .057 Uiso calc R 1 . . H C39 .1998(8) .3340(5) .8083(4) .0437(16) Uani d . 1 . . C H39 .2286 .3663 .7606 .052 Uiso calc R 1 . . H C40 .1453(8) .2271(5) .7848(4) .0442(16) Uani d . 1 . . C C41 .0478(8) .3928(6) .8385(4) .0532(18) Uani d . 1 . . C H41A .0088 .3601 .8837 .064 Uiso calc R 1 . . H H41B -.0529 .3930 .7994 .064 Uiso calc R 1 . . H C42 .0940(10) .4989(6) .8605(4) .0550(18) Uani d . 1 . . C H42A .1164 .5354 .8145 .066 Uiso calc R 1 . . H H42B -.0066 .5287 .8834 .066 Uiso calc R 1 . . H C43 .2589(9) .5017(6) .9174(4) .0493(17) Uani d . 1 . . C C44 .4137(9) .4481(6) .8801(4) .0532(18) Uani d . 1 . . C H44 .4185 .4779 .8290 .064 Uiso calc R 1 . . H C45 .5892(10) .4783(7) .9261(5) .064(2) Uani d . 1 . . C H45A .6094 .4414 .9737 .076 Uiso calc R 1 . . H H45B .6917 .4706 .8958 .076 Uiso calc R 1 . . H C46 .5524(11) .5838(7) .9419(4) .071(2) Uani d . 1 . . C C47 .3530(11) .6003(6) .9359(4) .059(2) Uani d . 1 . . C C48 .2849(11) .6891(7) .9477(4) .065(2) Uani d . 1 . . C H48 .3697 .7381 .9577 .078 Uiso calc R 1 . . H C49 .0969(12) .7203(7) .9472(5) .080(3) Uani d . 1 . . C H49A .0568 .7450 .8970 .120 Uiso calc R 1 . . H H49B .0873 .7705 .9852 .120 Uiso calc R 1 . . H H49C .0236 .6659 .9593 .120 Uiso calc R 1 . . H C50 .0823(11) .1704(6) .8531(4) .064(2) Uani d . 1 . . C H50A -.0405 .1868 .8598 .095 Uiso calc R 1 . . H H50B .1564 .1868 .8992 .095 Uiso calc R 1 . . H H50C .0913 .1019 .8434 .095 Uiso calc R 1 . . H C51 .2240(12) .4579(7) .9977(4) .073(2) Uani d . 1 . . C H51A .1321 .4948 1.0199 .110 Uiso calc R 1 . . H H51B .3328 .4604 1.0314 .110 Uiso calc R 1 . . H H51C .1856 .3915 .9912 .110 Uiso calc R 1 . . H O31 .1349(10) .0565(5) .5829(4) .098(2) Uani d . 1 . . O O32 .6673(8) .6438(6) .9587(4) .093(2) Uani d . 1 . . O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 .061(4) .052(4) .057(4) .011(4) .008(3) -.002(4) C2 .076(5) .051(5) .063(4) .006(4) .022(4) -.007(4) C3 .111(7) .057(5) .044(4) .006(5) -.002(4) -.005(4) C4 .063(5) .074(6) .065(5) -.013(5) -.003(4) -.024(4) C5 .044(4) .051(4) .049(4) -.004(3) -.002(3) -.004(3) C6 .052(4) .081(6) .082(5) -.016(4) .001(4) -.037(5) C7 .045(4) .068(5) .072(5) .000(4) .003(3) -.019(4) C8 .029(3) .051(4) .049(4) -.002(3) .006(3) -.003(3) C9 .039(3) .040(4) .038(3) -.001(3) -.001(3) -.001(3) C10 .044(3) .040(4) .044(3) .006(3) .007(3) -.003(3) C11 .032(3) .049(4) .061(4) .006(3) .006(3) -.008(4) C12 .038(3) .056(4) .053(4) -.006(3) .002(3) -.010(3) C13 .039(3) .043(4) .038(3) -.004(3) -.003(3) .005(3) C14 .028(3) .053(4) .041(3) -.002(3) .000(3) -.001(3) C15 .042(4) .059(5) .065(4) .005(4) -.003(3) .000(4) C16 .078(5) .045(5) .057(4) .014(4) .007(4) -.001(4) C17 .066(5) .035(4) .046(4) .002(4) .015(3) .004(3) C18 .082(6) .043(4) .061(4) -.004(4) .020(4) -.003(4) C19 .108(7) .068(6) .085(6) -.036(6) .011(5) -.021(5) C20 .126(8) .047(5) .054(4) -.004(5) .026(5) .004(4) C21 .085(5) .053(5) .044(4) .008(4) .010(4) .004(3) O1 .154(6) .114(6) .067(4) .040(5) -.008(4) -.049(4) O2 .104(5) .054(4) .100(4) .032(4) -.005(4) -.008(3) C31 .056(4) .050(4) .064(4) .011(4) .003(4) -.001(4) C32 .056(4) .058(5) .072(5) -.010(4) -.020(4) -.003(4) C33 .082(6) .053(5) .062(5) .011(4) .002(4) .000(4) C34 .065(5) .055(5) .067(5) .015(4) .008(4) .004(4) C35 .047(4) .050(4) .060(4) .006(3) -.002(3) .010(4) C36 .044(4) .064(5) .081(5) .018(4) .001(4) -.003(4) C37 .038(4) .071(5) .071(5) .002(4) -.001(3) .005(4) C38 .034(3) .056(4) .052(4) .000(3) .002(3) .003(3) C39 .034(3) .051(4) .045(3) .005(3) -.003(3) .007(3) C40 .037(3) .049(4) .046(3) .006(3) -.005(3) .002(3) C41 .033(3) .062(5) .063(4) -.003(3) -.005(3) -.001(4) C42 .054(4) .054(5) .057(4) .004(4) .004(3) .002(4) C43 .050(4) .058(5) .040(3) -.006(4) .005(3) -.002(3) C44 .048(4) .066(5) .046(3) -.007(4) .006(3) .002(4) C45 .048(4) .076(6) .068(5) .000(4) .012(3) -.006(4) C46 .073(5) .084(7) .055(4) -.035(5) .007(4) -.013(4) C47 .070(5) .069(6) .039(4) -.021(4) .009(3) -.005(4) C48 .070(5) .074(6) .051(4) -.016(5) .010(4) -.012(4) C49 .093(6) .077(7) .074(5) -.012(6) .036(5) -.011(5) C50 .066(5) .061(5) .064(4) -.004(4) .007(4) .005(4) C51 .085(6) .080(6) .058(4) -.015(5) .025(4) .000(4) O31 .128(5) .088(5) .075(4) .016(4) -.009(4) -.032(4) O32 .079(4) .089(5) .107(5) -.023(4) -.015(3) -.012(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.513(11) ? C1 C10 . 1.526(9) ? C1 H1A . .970 ? C1 H1B . .970 ? C2 C3 . 1.510(11) ? C2 H2A . .970 ? C2 H2B . .970 ? C3 O1 . 1.227(9) ? C3 C4 . 1.453(12) ? C4 C5 . 1.330(10) ? C4 H4 . .930 ? C5 C6 . 1.484(10) ? C5 C10 . 1.546(9) ? C6 C7 . 1.525(12) ? C6 H6A . .970 ? C6 H6B . .970 ? C7 C8 . 1.537(9) ? C7 H7A . .970 ? C7 H7B . .970 ? C8 C14 . 1.503(10) ? C8 C9 . 1.536(8) ? C8 H8 . .980 ? C9 C11 . 1.551(9) ? C9 C10 . 1.552(9) ? C9 H9 . .980 ? C10 C20 . 1.549(10) ? C11 C12 . 1.530(10) ? C11 H11A . .970 ? C11 H11B . .970 ? C12 C13 . 1.499(9) ? C12 H12A . .970 ? C12 H12B . .970 ? C13 C17 . 1.517(10) ? C13 C21 . 1.543(9) ? C13 C14 . 1.556(8) ? C14 C15 . 1.524(10) ? C14 H14 . .980 ? C15 C16 . 1.518(11) ? C15 H15A . .970 ? C15 H15B . .970 ? C16 O2 . 1.228(9) ? C16 C17 . 1.470(11) ? C17 C18 . 1.328(10) ? C18 C19 . 1.480(12) ? C18 H18 . .930 ? C19 H19A . .960 ? C19 H19B . .960 ? C19 H19C . .960 ? C20 H20A . .960 ? C20 H20B . .960 ? C20 H20C . .960 ? C21 H21A . .960 ? C21 H21B . .960 ? C21 H21C . .960 ? C31 C32 . 1.536(11) ? C31 C40 . 1.540(9) ? C31 H31A . .970 ? C31 H31B . .970 ? C32 C33 . 1.513(11) ? C32 H32A . .970 ? C32 H32B . .970 ? C33 O31 . 1.233(10) ? C33 C34 . 1.428(11) ? C34 C35 . 1.340(10) ? C34 H34 . .930 ? C35 C36 . 1.468(10) ? C35 C40 . 1.541(9) ? C36 C37 . 1.546(11) ? C36 H36A . .970 ? C36 H36B . .970 ? C37 C38 . 1.534(9) ? C37 H37A . .970 ? C37 H37B . .970 ? C38 C44 . 1.542(11) ? C38 C39 . 1.548(9) ? C38 H38 . .980 ? C39 C41 . 1.522(10) ? C39 C40 . 1.570(10) ? C39 H39 . .980 ? C40 C50 . 1.526(10) ? C41 C42 . 1.539(11) ? C41 H41A . .970 ? C41 H41B . .970 ? C42 C43 . 1.511(10) ? C42 H42A . .970 ? C42 H42B . .970 ? C43 C47 . 1.548(11) ? C43 C44 . 1.557(10) ? C43 C51 . 1.560(10) ? C44 C45 . 1.532(10) ? C44 H44 . .980 ? C45 C46 . 1.506(13) ? C45 H45A . .970 ? C45 H45B . .970 ? C46 O32 . 1.207(10) ? C46 C47 . 1.500(12) ? C47 C48 . 1.345(12) ? C48 C49 . 1.466(12) ? C48 H48 . .930 ? C49 H49A . .960 ? C49 H49B . .960 ? C49 H49C . .960 ? C50 H50A . .960 ? C50 H50B . .960 ? C50 H50C . .960 ? C51 H51A . .960 ? C51 H51B . .960 ? C51 H51C . .960 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C2 C1 C10 113.8(6) C2 C1 H1A 108.8 C10 C1 H1A 108.8 C2 C1 H1B 108.8 C10 C1 H1B 108.8 H1A C1 H1B 107.7 C3 C2 C1 112.6(7) C3 C2 H2A 109.1 C1 C2 H2A 109.1 C3 C2 H2B 109.1 C1 C2 H2B 109.1 H2A C2 H2B 107.8 O1 C3 C4 122.1(8) O1 C3 C2 121.7(8) C4 C3 C2 116.2(6) C5 C4 C3 125.3(7) C5 C4 H4 117.4 C3 C4 H4 117.4 C4 C5 C6 121.4(6) C4 C5 C10 121.1(6) C6 C5 C10 117.5(6) C5 C6 C7 113.3(6) C5 C6 H6A 108.9 C7 C6 H6A 108.9 C5 C6 H6B 108.9 C7 C6 H6B 108.9 H6A C6 H6B 107.7 C6 C7 C8 111.3(7) C6 C7 H7A 109.4 C8 C7 H7A 109.4 C6 C7 H7B 109.4 C8 C7 H7B 109.4 H7A C7 H7B 108.0 C14 C8 C9 108.8(5) C14 C8 C7 111.3(6) C9 C8 C7 108.8(5) C14 C8 H8 109.3 C9 C8 H8 109.3 C7 C8 H8 109.3 C8 C9 C11 111.3(5) C8 C9 C10 114.6(5) C11 C9 C10 111.5(5) C8 C9 H9 106.2 C11 C9 H9 106.2 C10 C9 H9 106.2 C1 C10 C5 110.8(5) C1 C10 C20 109.1(6) C5 C10 C20 107.5(6) C1 C10 C9 109.4(6) C5 C10 C9 108.2(5) C20 C10 C9 111.8(5) C12 C11 C9 112.8(5) C12 C11 H11A 109.0 C9 C11 H11A 109.0 C12 C11 H11B 109.0 C9 C11 H11B 109.0 H11A C11 H11B 107.8 C13 C12 C11 112.5(6) C13 C12 H12A 109.1 C11 C12 H12A 109.1 C13 C12 H12B 109.1 C11 C12 H12B 109.1 H12A C12 H12B 107.8 C12 C13 C17 118.1(6) C12 C13 C21 111.4(6) C17 C13 C21 106.8(6) C12 C13 C14 106.6(5) C17 C13 C14 100.8(5) C21 C13 C14 112.9(5) C8 C14 C15 121.7(6) C8 C14 C13 113.9(5) C15 C14 C13 104.0(5) C8 C14 H14 105.3 C15 C14 H14 105.3 C13 C14 H14 105.3 C16 C15 C14 102.1(6) C16 C15 H15A 111.3 C14 C15 H15A 111.3 C16 C15 H15B 111.3 C14 C15 H15B 111.3 H15A C15 H15B 109.2 O2 C16 C17 128.8(8) O2 C16 C15 122.4(7) C17 C16 C15 108.9(6) C18 C17 C16 120.2(7) C18 C17 C13 132.0(7) C16 C17 C13 107.7(6) C17 C18 C19 128.7(8) C17 C18 H18 115.7 C19 C18 H18 115.7 C18 C19 H19A 109.5 C18 C19 H19B 109.5 H19A C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C10 C20 H20A 109.5 C10 C20 H20B 109.5 H20A C20 H20B 109.5 C10 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C13 C21 H21A 109.5 C13 C21 H21B 109.5 H21A C21 H21B 109.5 C13 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C32 C31 C40 114.2(6) C32 C31 H31A 108.7 C40 C31 H31A 108.7 C32 C31 H31B 108.7 C40 C31 H31B 108.7 H31A C31 H31B 107.6 C33 C32 C31 109.8(6) C33 C32 H32A 109.7 C31 C32 H32A 109.7 C33 C32 H32B 109.7 C31 C32 H32B 109.7 H32A C32 H32B 108.2 O31 C33 C34 123.8(8) O31 C33 C32 117.9(8) C34 C33 C32 118.1(7) C35 C34 C33 123.3(7) C35 C34 H34 118.4 C33 C34 H34 118.4 C34 C35 C36 120.9(7) C34 C35 C40 123.7(6) C36 C35 C40 115.3(6) C35 C36 C37 114.0(6) C35 C36 H36A 108.8 C37 C36 H36A 108.8 C35 C36 H36B 108.8 C37 C36 H36B 108.8 H36A C36 H36B 107.6 C38 C37 C36 109.2(6) C38 C37 H37A 109.8 C36 C37 H37A 109.8 C38 C37 H37B 109.8 C36 C37 H37B 109.8 H37A C37 H37B 108.3 C37 C38 C44 110.8(6) C37 C38 C39 110.9(6) C44 C38 C39 107.6(5) C37 C38 H38 109.1 C44 C38 H38 109.1 C39 C38 H38 109.1 C41 C39 C38 111.4(5) C41 C39 C40 113.7(5) C38 C39 C40 113.1(5) C41 C39 H39 105.9 C38 C39 H39 105.9 C40 C39 H39 105.9 C50 C40 C31 110.6(6) C50 C40 C35 109.9(6) C31 C40 C35 108.7(5) C50 C40 C39 111.5(6) C31 C40 C39 107.9(5) C35 C40 C39 108.0(6) C39 C41 C42 115.5(6) C39 C41 H41A 108.4 C42 C41 H41A 108.4 C39 C41 H41B 108.4 C42 C41 H41B 108.4 H41A C41 H41B 107.5 C43 C42 C41 109.8(6) C43 C42 H42A 109.7 C41 C42 H42A 109.7 C43 C42 H42B 109.7 C41 C42 H42B 109.7 H42A C42 H42B 108.2 C42 C43 C47 119.2(7) C42 C43 C44 108.0(6) C47 C43 C44 99.3(6) C42 C43 C51 112.7(6) C47 C43 C51 105.1(6) C44 C43 C51 112.0(7) C45 C44 C38 120.2(6) C45 C44 C43 106.7(6) C38 C44 C43 112.9(6) C45 C44 H44 105.3 C38 C44 H44 105.3 C43 C44 H44 105.3 C46 C45 C44 101.3(7) C46 C45 H45A 111.5 C44 C45 H45A 111.5 C46 C45 H45B 111.5 C44 C45 H45B 111.5 H45A C45 H45B 109.3 O32 C46 C47 126.4(9) O32 C46 C45 124.4(8) C47 C46 C45 109.1(7) C48 C47 C46 120.8(7) C48 C47 C43 131.0(7) C46 C47 C43 108.2(7) C47 C48 C49 129.7(8) C47 C48 H48 115.1 C49 C48 H48 115.1 C48 C49 H49A 109.5 C48 C49 H49B 109.5 H49A C49 H49B 109.5 C48 C49 H49C 109.5 H49A C49 H49C 109.5 H49B C49 H49C 109.5 C40 C50 H50A 109.5 C40 C50 H50B 109.5 H50A C50 H50B 109.5 C40 C50 H50C 109.5 H50A C50 H50C 109.5 H50B C50 H50C 109.5 C43 C51 H51A 109.5 C43 C51 H51B 109.5 H51A C51 H51B 109.5 C43 C51 H51C 109.5 H51A C51 H51C 109.5 H51B C51 H51C 109.5 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C21 H21C O2 2_656 .96 2.745 3.625(10) 153 yes C21 H21B O31 2_656 .96 2.813 3.723(10) 159 yes C32 H32B O2 1_455 .97 2.453 3.237(10) 138 yes C45 H45A O1 2_647 .97 2.425 3.274(11) 146 yes C50 H50B O32 2_647 .96 2.759 3.641(10) 153 yes C51 H51B O1 2_647 .96 2.725 3.678(12) 172 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_publ_flag C10 C1 C2 C3 -52.0(8) yes C1 C2 C3 O1 -154.1(9) ? C1 C2 C3 C4 29.3(10) yes O1 C3 C4 C5 -177.9(9) ? C2 C3 C4 C5 -1.3(13) yes C3 C4 C5 C6 172.5(8) ? C3 C4 C5 C10 -4.6(13) yes C4 C5 C6 C7 134.8(8) ? C10 C5 C6 C7 -48.0(10) yes C5 C6 C7 C8 52.5(9) yes C6 C7 C8 C14 -176.7(6) ? C6 C7 C8 C9 -56.8(8) yes C14 C8 C9 C11 -52.5(7) ? C7 C8 C9 C11 -173.9(6) ? C14 C8 C9 C10 179.7(5) ? C7 C8 C9 C10 58.3(7) yes C2 C1 C10 C5 45.3(8) yes C2 C1 C10 C20 -72.9(8) yes C2 C1 C10 C9 164.5(6) ? C4 C5 C10 C1 -17.5(10) yes C6 C5 C10 C1 165.3(7) ? C4 C5 C10 C20 101.7(8) ? C6 C5 C10 C20 -75.5(8) ? C4 C5 C10 C9 -137.4(7) ? C6 C5 C10 C9 45.3(8) yes C8 C9 C10 C1 -171.6(5) ? C11 C9 C10 C1 60.8(7) ? C8 C9 C10 C5 -50.8(7) yes C11 C9 C10 C5 -178.4(5) ? C8 C9 C10 C20 67.4(8) ? C11 C9 C10 C20 -60.2(8) ? C8 C9 C11 C12 50.9(8) ? C10 C9 C11 C12 -179.7(6) ? C9 C11 C12 C13 -54.5(8) ? C11 C12 C13 C17 168.8(6) ? C11 C12 C13 C21 -67.0(8) yes C11 C12 C13 C14 56.5(7) ? C9 C8 C14 C15 -174.3(6) ? C7 C8 C14 C15 -54.5(8) ? C9 C8 C14 C13 59.8(7) ? C7 C8 C14 C13 179.7(5) ? C12 C13 C14 C8 -61.4(7) ? C17 C13 C14 C8 174.7(5) ? C21 C13 C14 C8 61.2(7) ? C12 C13 C14 C15 163.9(6) ? C17 C13 C14 C15 40.0(6) yes C21 C13 C14 C15 -73.5(7) ? C8 C14 C15 C16 -167.1(6) ? C13 C14 C15 C16 -36.8(7) yes C14 C15 C16 O2 -160.5(7) ? C14 C15 C16 C17 19.7(8) yes O2 C16 C17 C18 3.2(12) ? C15 C16 C17 C18 -177.1(6) ? O2 C16 C17 C13 -174.2(8) ? C15 C16 C17 C13 5.6(8) yes C12 C13 C17 C18 39.7(11) ? C21 C13 C17 C18 -86.7(9) ? C14 C13 C17 C18 155.3(7) ? C12 C13 C17 C16 -143.3(6) ? C21 C13 C17 C16 90.3(7) ? C14 C13 C17 C16 -27.8(6) yes C16 C17 C18 C19 -174.5(7) yes C13 C17 C18 C19 2.1(13) ? C40 C31 C32 C33 -54.8(9) yes C31 C32 C33 O31 -151.6(8) ? C31 C32 C33 C34 33.3(10) yes O31 C33 C34 C35 -179.5(9) ? C32 C33 C34 C35 -4.6(12) yes C33 C34 C35 C36 171.5(8) ? C33 C34 C35 C40 -4.7(12) yes C34 C35 C36 C37 129.3(8) ? C40 C35 C36 C37 -54.2(9) yes C35 C36 C37 C38 54.4(9) yes C36 C37 C38 C44 -174.3(6) ? C36 C37 C38 C39 -54.9(8) yes C37 C38 C39 C41 -173.6(6) ? C44 C38 C39 C41 -52.2(7) ? C37 C38 C39 C40 56.8(8) yes C44 C38 C39 C40 178.2(6) ? C32 C31 C40 C50 -75.4(8) yes C32 C31 C40 C35 45.4(8) yes C32 C31 C40 C39 162.4(6) ? C34 C35 C40 C50 105.4(8) ? C36 C35 C40 C50 -70.9(8) ? C34 C35 C40 C31 -15.8(10) yes C36 C35 C40 C31 167.8(6) ? C34 C35 C40 C39 -132.7(7) ? C36 C35 C40 C39 50.9(8) yes C41 C39 C40 C50 -59.5(7) ? C38 C39 C40 C50 68.9(7) ? C41 C39 C40 C31 62.2(7) ? C38 C39 C40 C31 -169.4(5) ? C41 C39 C40 C35 179.6(5) ? C38 C39 C40 C35 -52.0(7) yes C38 C39 C41 C42 52.1(8) ? C40 C39 C41 C42 -178.6(6) ? C39 C41 C42 C43 -54.2(8) ? C41 C42 C43 C47 168.3(6) ? C41 C42 C43 C44 56.2(8) ? C41 C42 C43 C51 -68.0(8) yes C37 C38 C44 C45 -51.6(9) ? C39 C38 C44 C45 -173.0(6) ? C37 C38 C44 C43 -179.0(6) ? C39 C38 C44 C43 59.6(7) ? C42 C43 C44 C45 163.0(6) ? C47 C43 C44 C45 38.1(7) yes C51 C43 C44 C45 -72.4(8) ? C42 C43 C44 C38 -62.8(8) ? C47 C43 C44 C38 172.3(6) ? C51 C43 C44 C38 61.8(8) ? C38 C44 C45 C46 -168.2(6) ? C43 C44 C45 C46 -38.0(8) yes C44 C45 C46 O32 -159.7(8) ? C44 C45 C46 C47 22.2(8) yes O32 C46 C47 C48 1.7(13) ? C45 C46 C47 C48 179.8(7) ? O32 C46 C47 C43 -176.9(8) ? C45 C46 C47 C43 1.2(8) yes C42 C43 C47 C48 41.4(11) ? C44 C43 C47 C48 158.1(8) ? C51 C43 C47 C48 -86.0(10) ? C42 C43 C47 C46 -140.2(6) ? C44 C43 C47 C46 -23.5(7) yes C51 C43 C47 C46 92.4(7) ? C46 C47 C48 C49 -177.8(7) yes C43 C47 C48 C49 .4(14) ? C16 C17 C18 C19 -174.5(7) ? C46 C47 C48 C49 -177.8(7) ? H9 C9 C8 H8 -178.0 yes H39 C39 C38 H38 -179.1 yes C21 C13 C14 H14 176.0 yes C51 C43 C44 H44 176.1 yes _cod_database_fobs_code 2200132