#------------------------------------------------------------------------------
#$Date: 2024-12-25 04:30:03 +0200 (Wed, 25 Dec 2024) $
#$Revision: 296966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/35/1573537.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_1573537
_journal_coeditor_code           OX2011
_journal_paper_doi               10.1107/S2056989024012234
_chemical_formula_iupac          'C38 H48 O11'
_chemical_formula_moiety         'C38 H48 O11'
_chemical_formula_sum            'C38 H48 O11'
_chemical_formula_weight         680.76
_chemical_melting_point_gt       476.5
_chemical_melting_point_lt       478
_chemical_name_systematic
'(+-)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR,14SR,15SR,16RS)-13-Acetoxy-16-benzyloxy-15-hydroxy-7-methoxymethoxy-3-oxo-11,15,18,18-tetramethyl-2,4-dioxatetracyclo[12.3.1.0^1,5^.0^6,11^]octadecan-10-yl benzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.304(2)
_cell_angle_beta                 94.004(2)
_cell_angle_gamma                93.651(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6913(7)
_cell_length_b                   11.8313(8)
_cell_length_c                   14.9295(9)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    90
_cell_measurement_theta_max      24.6799
_cell_measurement_theta_min      2.3364
_cell_volume                     1692.9(2)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCif (Westrip, 2010) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2019 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0896
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15750
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         5809
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.6809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                3577
_reflns_number_total             5809
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ox2011.cif
_cod_data_source_block           B
_cod_database_code               1573537
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8584(2) 1.01872(17) 0.18691(13) 0.0200(5) Uani d 1.000000 . .
C C2 0.7051(2) 0.97852(17) 0.15839(13) 0.0191(5) Uani d 1.000000 . .
H H2 0.649435 1.011920 0.207354 0.023000 Uiso calc 1.000000 . .
C C3 0.6600(2) 0.85028(17) 0.14210(13) 0.0178(5) Uani d 1.000000 . .
H H3 0.745136 0.808839 0.153552 0.021000 Uiso calc 1.000000 . .
C C4 0.6051(2) 0.81211(18) 0.04417(14) 0.0250(6) Uani d 1.000000 . .
H H4 0.529296 0.859996 0.025251 0.030000 Uiso calc 1.000000 . .
C C5 0.5540(3) 0.68564(18) 0.03201(15) 0.0323(6) Uani d 1.000000 . .
H H5A 0.506930 0.666041 -0.029242 0.039000 Uiso calc 1.000000 . .
H H5B 0.634889 0.638951 0.036737 0.039000 Uiso calc 1.000000 . .
C C6 0.4549(2) 0.65616(19) 0.10148(15) 0.0303(6) Uani d 1.000000 . .
H H6A 0.368939 0.696009 0.093016 0.036000 Uiso calc 1.000000 . .
H H6B 0.429691 0.573058 0.093685 0.036000 Uiso calc 1.000000 . .
C C7 0.5233(2) 0.69191(18) 0.19519(14) 0.0230(5) Uani d 1.000000 . .
H H7 0.610172 0.651344 0.202360 0.028000 Uiso calc 1.000000 . .
C C8 0.5608(2) 0.82212(17) 0.21438(14) 0.0189(5) Uani d 1.000000 . .
C C9 0.6334(2) 0.83985(17) 0.31171(13) 0.0209(5) Uani d 1.000000 . .
H H9A 0.562886 0.812449 0.350731 0.025000 Uiso calc 1.000000 . .
H H9B 0.705526 0.784250 0.311368 0.025000 Uiso calc 1.000000 . .
C C10 0.7037(2) 0.95049(18) 0.36518(14) 0.0273(6) Uani d 1.000000 . .
H H10 0.711752 0.931768 0.428963 0.033000 Uiso calc 1.000000 . .
C C11 0.8497(2) 1.00841(18) 0.35329(14) 0.0275(6) Uani d 1.000000 . .
H H11 0.872348 1.058574 0.411532 0.033000 Uiso calc 1.000000 . .
C C12 0.9612(2) 0.91953(19) 0.35470(14) 0.0272(6) Uani d 1.000000 . .
C C13 0.9669(2) 0.85450(18) 0.26075(14) 0.0213(5) Uani d 1.000000 . .
H H13 0.885099 0.797483 0.249506 0.026000 Uiso calc 1.000000 . .
C C14 0.9653(2) 0.92946(18) 0.18310(14) 0.0229(5) Uani d 1.000000 . .
H H14A 1.058505 0.968900 0.183074 0.028000 Uiso calc 1.000000 . .
H H14B 0.947357 0.879446 0.125242 0.028000 Uiso calc 1.000000 . .
C C15 0.8702(3) 1.09239(18) 0.27930(15) 0.0294(6) Uani d 1.000000 . .
C C16 0.7663(3) 1.18656(18) 0.28164(16) 0.0413(7) Uani d 1.000000 . .
H H16A 0.785421 1.236535 0.235135 0.062000 Uiso calc 1.000000 . .
H H16B 0.776070 1.231434 0.341229 0.062000 Uiso calc 1.000000 . .
H H16C 0.671494 1.151321 0.270042 0.062000 Uiso calc 1.000000 . .
C C17 1.0129(3) 1.1615(2) 0.29506(17) 0.0467(8) Uani d 1.000000 . .
H H17A 1.086776 1.110351 0.282773 0.070000 Uiso calc 1.000000 . .
H H17B 1.026175 1.196576 0.357913 0.070000 Uiso calc 1.000000 . .
H H17C 1.016083 1.221111 0.254443 0.070000 Uiso calc 1.000000 . .
C C18 0.9425(3) 0.83633(19) 0.42508(14) 0.0309(6) Uani d 1.000000 . .
H H18A 1.026068 0.794578 0.431805 0.046000 Uiso calc 1.000000 . .
H H18B 0.862485 0.782296 0.405338 0.046000 Uiso calc 1.000000 . .
H H18C 0.926940 0.878766 0.483216 0.046000 Uiso calc 1.000000 . .
C C19 0.4281(2) 0.88623(18) 0.20956(15) 0.0265(6) Uani d 1.000000 . .
H H19A 0.382138 0.871255 0.148436 0.040000 Uiso calc 1.000000 . .
H H19B 0.451959 0.968247 0.224121 0.040000 Uiso calc 1.000000 . .
H H19C 0.365526 0.860099 0.253065 0.040000 Uiso calc 1.000000 . .
O O20 0.67221(15) 1.03694(11) 0.07988(9) 0.0237(4) Uani d 1.000000 . .
C C21 0.7839(2) 1.09881(18) 0.05953(15) 0.0224(5) Uani d 1.000000 . .
O O22 0.89293(15) 1.09196(12) 0.11742(9) 0.0251(4) Uani d 1.000000 . .
O O23 0.78395(16) 1.15486(12) -0.00246(10) 0.0309(4) Uani d 1.000000 . .
O O24 0.43036(15) 0.65942(12) 0.26233(10) 0.0267(4) Uani d 1.000000 . .
C C25 0.4325(5) 0.5480(5) 0.2765(4) 0.0212(12) Uani d 0.499(3) A 1
O O26 0.5034(3) 0.4781(3) 0.2418(2) 0.0298(10) Uani d 0.499(3) A 1
C C27 0.3419(5) 0.5281(4) 0.3499(4) 0.0186(12) Uani d 0.499(3) A 1
C C28 0.3138(5) 0.4168(4) 0.3681(3) 0.0237(11) Uani d 0.499(3) A 1
H H28 0.348877 0.355343 0.332241 0.028000 Uiso calc 0.499(3) A 1
C C29 0.2347(5) 0.3960(4) 0.4385(3) 0.0261(12) Uani d 0.499(3) A 1
H H29 0.214081 0.319269 0.449194 0.031000 Uiso calc 0.499(3) A 1
C C30 0.1847(9) 0.4815(6) 0.4935(5) 0.0282(18) Uani d 0.499(3) A 1
H H30 0.133510 0.464943 0.543012 0.034000 Uiso calc 0.499(3) A 1
C C31 0.2114(14) 0.5973(14) 0.4746(12) 0.027(3) Uani d 0.499(3) A 1
H H31 0.175916 0.659433 0.509461 0.032000 Uiso calc 0.499(3) A 1
C C32 0.2918(14) 0.6139(14) 0.4025(11) 0.025(3) Uani d 0.499(3) A 1
H H32 0.312447 0.689838 0.389795 0.030000 Uiso calc 0.499(3) A 1
C C25D 0.4773(6) 0.5905(4) 0.3285(4) 0.0242(12) Uani d 0.501(3) A 2
O O26D 0.5882(4) 0.5498(3) 0.3245(2) 0.0505(12) Uani d 0.501(3) A 2
C C27D 0.3793(6) 0.5664(5) 0.3954(4) 0.0178(12) Uani d 0.501(3) A 2
C C28D 0.4112(5) 0.4859(4) 0.4534(3) 0.0273(12) Uani d 0.501(3) A 2
H H28D 0.494422 0.448218 0.448256 0.033000 Uiso calc 0.501(3) A 2
C C29D 0.3237(5) 0.4600(4) 0.5181(3) 0.0302(12) Uani d 0.501(3) A 2
H H29D 0.345307 0.404208 0.557048 0.036000 Uiso calc 0.501(3) A 2
C C30D 0.2042(9) 0.5164(6) 0.5256(5) 0.033(2) Uani d 0.501(3) A 2
H H30D 0.143303 0.498983 0.570166 0.040000 Uiso calc 0.501(3) A 2
C C31D 0.1725(16) 0.5949(15) 0.4714(13) 0.032(3) Uani d 0.501(3) A 2
H H31D 0.087990 0.630649 0.477118 0.039000 Uiso calc 0.501(3) A 2
C C32D 0.2592(14) 0.6257(13) 0.4072(11) 0.017(2) Uani d 0.501(3) A 2
H H32D 0.238292 0.685344 0.371817 0.020000 Uiso calc 0.501(3) A 2
O O33 0.59875(19) 1.03335(13) 0.36604(10) 0.0378(5) Uani d 1.000000 . .
C C34 0.5799(3) 1.0968(2) 0.44472(18) 0.0382(7) Uani d 1.000000 . .
O O35 0.64598(19) 1.08938(14) 0.51481(11) 0.0415(5) Uani d 1.000000 . .
C C36 0.4661(3) 1.1731(2) 0.42989(19) 0.0600(9) Uani d 1.000000 . .
H H36A 0.453922 1.220302 0.486550 0.090000 Uiso calc 1.000000 . .
H H36B 0.379770 1.126822 0.409696 0.090000 Uiso calc 1.000000 . .
H H36C 0.489674 1.222243 0.383663 0.090000 Uiso calc 1.000000 . .
O O37 1.08981(15) 0.79399(12) 0.26522(10) 0.0274(4) Uani d 1.000000 . .
C C38 1.1025(2) 0.71208(19) 0.18821(15) 0.0287(6) Uani d 1.000000 . .
H H38A 1.191912 0.676937 0.196142 0.034000 Uiso calc 1.000000 . .
H H38B 1.104522 0.752330 0.133529 0.034000 Uiso calc 1.000000 . .
C C39 0.9871(2) 0.61915(18) 0.17341(14) 0.0218(5) Uani d 1.000000 . .
C C40 0.9304(3) 0.5816(2) 0.08837(16) 0.0408(7) Uani d 1.000000 . .
H H40 0.960170 0.617578 0.038506 0.049000 Uiso calc 1.000000 . .
C C41 0.8296(3) 0.4915(2) 0.0738(2) 0.0573(9) Uani d 1.000000 . .
H H41 0.792518 0.465052 0.014086 0.069000 Uiso calc 1.000000 . .
C C42 0.7837(3) 0.4409(2) 0.1447(2) 0.0426(7) Uani d 1.000000 . .
H H42 0.714454 0.379419 0.134634 0.051000 Uiso calc 1.000000 . .
C C43 0.8375(3) 0.4789(2) 0.23040(18) 0.0405(7) Uani d 1.000000 . .
H H43 0.804578 0.444878 0.280332 0.049000 Uiso calc 1.000000 . .
C C44 0.9395(3) 0.5665(2) 0.24428(16) 0.0359(7) Uani d 1.000000 . .
H H44 0.978049 0.591329 0.304003 0.043000 Uiso calc 1.000000 . .
O O45 1.09175(17) 0.98315(13) 0.38187(11) 0.0367(5) Uani d 1.000000 . .
H H45 1.155296 0.938151 0.383312 0.055000 Uiso calc 1.000000 . .
O O46 0.72244(18) 0.82882(12) -0.00707(10) 0.0356(4) Uani d 1.000000 . .
C C47 0.7298(9) 0.8448(7) -0.0938(6) 0.033(2) Uani d 0.495(4) B 3
H H47A 0.822280 0.881211 -0.101774 0.040000 Uiso calc 0.495(4) B 3
H H47B 0.659356 0.897289 -0.110632 0.040000 Uiso calc 0.495(4) B 3
O O48 0.7079(4) 0.7415(4) -0.1521(2) 0.0328(11) Uani d 0.495(4) B 3
C C49 0.8157(5) 0.6683(4) -0.1399(3) 0.0328(15) Uani d 0.495(4) B 3
H H49A 0.904539 0.713654 -0.127697 0.049000 Uiso calc 0.495(4) B 3
H H49B 0.818482 0.615162 -0.194833 0.049000 Uiso calc 0.495(4) B 3
H H49C 0.798756 0.625307 -0.088785 0.049000 Uiso calc 0.495(4) B 3
C C47D 0.6639(8) 0.8663(7) -0.0941(6) 0.0284(19) Uani d 0.505(4) B 4
H H47D 0.613226 0.934996 -0.078710 0.034000 Uiso calc 0.505(4) B 4
H H47E 0.742871 0.889946 -0.128149 0.034000 Uiso calc 0.505(4) B 4
O O48D 0.5756(4) 0.7894(3) -0.1522(2) 0.0379(13) Uani d 0.505(4) B 4
C C49D 0.6421(8) 0.6943(6) -0.1870(4) 0.0491(17) Uani d 0.505(4) B 4
H H49D 0.717544 0.719139 -0.222313 0.074000 Uiso calc 0.505(4) B 4
H H49E 0.575198 0.641821 -0.225880 0.074000 Uiso calc 0.505(4) B 4
H H49F 0.679983 0.655508 -0.137022 0.074000 Uiso calc 0.505(4) B 4
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O22 C1 C14 . . 105.13(16) ?
O22 C1 C15 . . 108.54(16) ?
C14 C1 C15 . . 111.58(18) ?
O22 C1 C2 . . 102.40(15) ?
C14 C1 C2 . . 118.03(17) ?
C15 C1 C2 . . 110.25(18) ?
O20 C2 C3 . . 112.46(16) ?
O20 C2 C1 . . 103.90(15) ?
C3 C2 C1 . . 120.11(18) ?
O20 C2 H2 . . 106.500000 ?
C3 C2 H2 . . 106.500000 ?
C1 C2 H2 . . 106.500000 ?
C4 C3 C2 . . 112.45(16) ?
C4 C3 C8 . . 115.39(17) ?
C2 C3 C8 . . 108.34(17) ?
C4 C3 H3 . . 106.700000 ?
C2 C3 H3 . . 106.700000 ?
C8 C3 H3 . . 106.700000 ?
O46 C4 C3 . . 104.44(17) ?
O46 C4 C5 . . 109.71(19) ?
C3 C4 C5 . . 110.80(17) ?
O46 C4 H4 . . 110.600000 ?
C3 C4 H4 . . 110.600000 ?
C5 C4 H4 . . 110.600000 ?
C6 C5 C4 . . 112.6(2) ?
C6 C5 H5A . . 109.100000 ?
C4 C5 H5A . . 109.100000 ?
C6 C5 H5B . . 109.100000 ?
C4 C5 H5B . . 109.100000 ?
H5A C5 H5B . . 107.800000 ?
C7 C6 C5 . . 109.32(18) ?
C7 C6 H6A . . 109.800000 ?
C5 C6 H6A . . 109.800000 ?
C7 C6 H6B . . 109.800000 ?
C5 C6 H6B . . 109.800000 ?
H6A C6 H6B . . 108.300000 ?
O24 C7 C6 . . 109.50(17) ?
O24 C7 C8 . . 108.01(17) ?
C6 C7 C8 . . 113.13(17) ?
O24 C7 H7 . . 108.700000 ?
C6 C7 H7 . . 108.700000 ?
C8 C7 H7 . . 108.700000 ?
C19 C8 C3 . . 112.98(16) ?
C19 C8 C7 . . 109.77(17) ?
C3 C8 C7 . . 105.29(17) ?
C19 C8 C9 . . 110.89(17) ?
C3 C8 C9 . . 112.59(17) ?
C7 C8 C9 . . 104.83(16) ?
C10 C9 C8 . . 128.84(17) ?
C10 C9 H9A . . 105.100000 ?
C8 C9 H9A . . 105.100000 ?
C10 C9 H9B . . 105.100000 ?
C8 C9 H9B . . 105.100000 ?
H9A C9 H9B . . 105.900000 ?
O33 C10 C9 . . 105.72(18) ?
O33 C10 C11 . . 110.82(17) ?
C9 C10 C11 . . 127.33(19) ?
O33 C10 H10 . . 103.400000 ?
C9 C10 H10 . . 103.400000 ?
C11 C10 H10 . . 103.400000 ?
C12 C11 C10 . . 110.26(17) ?
C12 C11 C15 . . 112.88(19) ?
C10 C11 C15 . . 121.09(19) ?
C12 C11 H11 . . 103.400000 ?
C10 C11 H11 . . 103.400000 ?
C15 C11 H11 . . 103.400000 ?
O45 C12 C18 . . 105.47(17) ?
O45 C12 C13 . . 109.83(18) ?
C18 C12 C13 . . 110.43(18) ?
O45 C12 C11 . . 106.34(17) ?
C18 C12 C11 . . 113.83(19) ?
C13 C12 C11 . . 110.69(17) ?
O37 C13 C12 . . 105.79(17) ?
O37 C13 C14 . . 111.37(17) ?
C12 C13 C14 . . 114.68(18) ?
O37 C13 H13 . . 108.300000 ?
C12 C13 H13 . . 108.300000 ?
C14 C13 H13 . . 108.300000 ?
C1 C14 C13 . . 115.06(18) ?
C1 C14 H14A . . 108.500000 ?
C13 C14 H14A . . 108.500000 ?
C1 C14 H14B . . 108.500000 ?
C13 C14 H14B . . 108.500000 ?
H14A C14 H14B . . 107.500000 ?
C1 C15 C16 . . 111.57(18) ?
C1 C15 C17 . . 110.3(2) ?
C16 C15 C17 . . 102.98(19) ?
C1 C15 C11 . . 106.92(16) ?
C16 C15 C11 . . 113.4(2) ?
C17 C15 C11 . . 111.71(18) ?
C15 C16 H16A . . 109.500000 ?
C15 C16 H16B . . 109.500000 ?
H16A C16 H16B . . 109.500000 ?
C15 C16 H16C . . 109.500000 ?
H16A C16 H16C . . 109.500000 ?
H16B C16 H16C . . 109.500000 ?
C15 C17 H17A . . 109.500000 ?
C15 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
C15 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
C12 C18 H18A . . 109.500000 ?
C12 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
C12 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?
C8 C19 H19A . . 109.500000 ?
C8 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C8 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
C21 O20 C2 . . 110.58(16) ?
O23 C21 O22 . . 124.5(2) ?
O23 C21 O20 . . 123.6(2) ?
O22 C21 O20 . . 111.86(18) ?
C21 O22 C1 . . 111.22(16) ?
C25 O24 C7 . . 113.5(3) ?
C25D O24 C7 . . 119.5(2) ?
O26 C25 O24 . . 127.1(4) ?
O26 C25 C27 . . 124.6(4) ?
O24 C25 C27 . . 108.1(4) ?
C32 C27 C28 . . 118.9(8) ?
C32 C27 C25 . . 122.8(8) ?
C28 C27 C25 . . 118.2(5) ?
C29 C28 C27 . . 119.6(4) ?
C29 C28 H28 . . 120.200000 ?
C27 C28 H28 . . 120.200000 ?
C30 C29 C28 . . 122.5(5) ?
C30 C29 H29 . . 118.800000 ?
C28 C29 H29 . . 118.800000 ?
C29 C30 C31 . . 118.5(9) ?
C29 C30 H30 . . 120.800000 ?
C31 C30 H30 . . 120.800000 ?
C32 C31 C30 . . 116.8(14) ?
C32 C31 H31 . . 121.600000 ?
C30 C31 H31 . . 121.600000 ?
C27 C32 C31 . . 123.7(14) ?
C27 C32 H32 . . 118.200000 ?
C31 C32 H32 . . 118.200000 ?
O26D C25D O24 . . 120.4(4) ?
O26D C25D C27D . . 123.7(4) ?
O24 C25D C27D . . 115.7(4) ?
C28D C27D C32D . . 118.8(8) ?
C28D C27D C25D . . 118.1(5) ?
C32D C27D C25D . . 123.1(8) ?
C29D C28D C27D . . 120.9(5) ?
C29D C28D H28D . . 119.600000 ?
C27D C28D H28D . . 119.600000 ?
C28D C29D C30D . . 118.9(5) ?
C28D C29D H29D . . 120.500000 ?
C30D C29D H29D . . 120.500000 ?
C31D C30D C29D . . 121.2(10) ?
C31D C30D H30D . . 119.400000 ?
C29D C30D H30D . . 119.400000 ?
C30D C31D C32D . . 121.8(14) ?
C30D C31D H31D . . 119.100000 ?
C32D C31D H31D . . 119.100000 ?
C31D C32D C27D . . 118.3(13) ?
C31D C32D H32D . . 120.800000 ?
C27D C32D H32D . . 120.800000 ?
C34 O33 C10 . . 118.91(19) ?
O35 C34 O33 . . 123.6(2) ?
O35 C34 C36 . . 126.9(2) ?
O33 C34 C36 . . 109.5(2) ?
C34 C36 H36A . . 109.500000 ?
C34 C36 H36B . . 109.500000 ?
H36A C36 H36B . . 109.500000 ?
C34 C36 H36C . . 109.500000 ?
H36A C36 H36C . . 109.500000 ?
H36B C36 H36C . . 109.500000 ?
C13 O37 C38 . . 114.57(16) ?
O37 C38 C39 . . 113.76(18) ?
O37 C38 H38A . . 108.800000 ?
C39 C38 H38A . . 108.800000 ?
O37 C38 H38B . . 108.800000 ?
C39 C38 H38B . . 108.800000 ?
H38A C38 H38B . . 107.700000 ?
C40 C39 C44 . . 118.1(2) ?
C40 C39 C38 . . 120.5(2) ?
C44 C39 C38 . . 121.3(2) ?
C39 C40 C41 . . 120.7(2) ?
C39 C40 H40 . . 119.600000 ?
C41 C40 H40 . . 119.600000 ?
C42 C41 C40 . . 120.3(2) ?
C42 C41 H41 . . 119.900000 ?
C40 C41 H41 . . 119.900000 ?
C41 C42 C43 . . 119.7(2) ?
C41 C42 H42 . . 120.100000 ?
C43 C42 H42 . . 120.100000 ?
C42 C43 C44 . . 119.8(2) ?
C42 C43 H43 . . 120.100000 ?
C44 C43 H43 . . 120.100000 ?
C43 C44 C39 . . 121.4(2) ?
C43 C44 H44 . . 119.300000 ?
C39 C44 H44 . . 119.300000 ?
C12 O45 H45 . . 109.500000 ?
C47 O46 C4 . . 130.7(4) ?
C4 O46 C47D . . 104.8(3) ?
O46 C47 O48 . . 112.4(6) ?
O46 C47 H47A . . 109.100000 ?
O48 C47 H47A . . 109.100000 ?
O46 C47 H47B . . 109.100000 ?
O48 C47 H47B . . 109.100000 ?
H47A C47 H47B . . 107.900000 ?
C49 O48 C47 . . 112.2(4) ?
O48 C49 H49A . . 109.500000 ?
O48 C49 H49B . . 109.500000 ?
H49A C49 H49B . . 109.500000 ?
O48 C49 H49C . . 109.500000 ?
H49A C49 H49C . . 109.500000 ?
H49B C49 H49C . . 109.500000 ?
O48D C47D O46 . . 118.6(6) ?
O48D C47D H47D . . 107.700000 ?
O46 C47D H47D . . 107.700000 ?
O48D C47D H47E . . 107.700000 ?
O46 C47D H47E . . 107.700000 ?
H47D C47D H47E . . 107.100000 ?
C47D O48D C49D . . 112.5(6) ?
O48D C49D H49D . . 109.500000 ?
O48D C49D H49E . . 109.500000 ?
H49D C49D H49E . . 109.500000 ?
O48D C49D H49F . . 109.500000 ?
H49D C49D H49F . . 109.500000 ?
H49E C49D H49F . . 109.500000 ?
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 O22 . 1.466(2) ?
C1 C14 . 1.525(3) ?
C1 C15 . 1.542(3) ?
C1 C2 . 1.547(3) ?
C2 O20 . 1.452(2) ?
C2 C3 . 1.540(3) ?
C2 H2 . 1.000000 ?
C3 C4 . 1.530(3) ?
C3 C8 . 1.544(3) ?
C3 H3 . 1.000000 ?
C4 O46 . 1.429(3) ?
C4 C5 . 1.533(3) ?
C4 H4 . 1.000000 ?
C5 C6 . 1.515(3) ?
C5 H5A . 0.990000 ?
C5 H5B . 0.990000 ?
C6 C7 . 1.510(3) ?
C6 H6A . 0.990000 ?
C6 H6B . 0.990000 ?
C7 O24 . 1.460(2) ?
C7 C8 . 1.551(3) ?
C7 H7 . 1.000000 ?
C8 C19 . 1.536(3) ?
C8 C9 . 1.556(3) ?
C9 C10 . 1.548(3) ?
C9 H9A . 0.990000 ?
C9 H9B . 0.990000 ?
C10 O33 . 1.457(3) ?
C10 C11 . 1.563(3) ?
C10 H10 . 1.000000 ?
C11 C12 . 1.556(3) ?
C11 C15 . 1.579(3) ?
C11 H11 . 1.000000 ?
C12 O45 . 1.439(3) ?
C12 C18 . 1.529(3) ?
C12 C13 . 1.530(3) ?
C13 O37 . 1.430(2) ?
C13 C14 . 1.535(3) ?
C13 H13 . 1.000000 ?
C14 H14A . 0.990000 ?
C14 H14B . 0.990000 ?
C15 C16 . 1.548(3) ?
C15 C17 . 1.551(3) ?
C16 H16A . 0.980000 ?
C16 H16B . 0.980000 ?
C16 H16C . 0.980000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
O20 C21 . 1.339(3) ?
C21 O23 . 1.196(2) ?
C21 O22 . 1.330(2) ?
O24 C25 . 1.359(5) ?
O24 C25D . 1.418(5) ?
C25 O26 . 1.205(5) ?
C25 C27 . 1.480(7) ?
C27 C32 . 1.351(14) ?
C27 C28 . 1.388(6) ?
C28 C29 . 1.378(6) ?
C28 H28 . 0.950000 ?
C29 C30 . 1.367(9) ?
C29 H29 . 0.950000 ?
C30 C31 . 1.440(18) ?
C30 H30 . 0.950000 ?
C31 C32 . 1.395(17) ?
C31 H31 . 0.950000 ?
C32 H32 . 0.950000 ?
C25D O26D . 1.208(5) ?
C25D C27D . 1.464(7) ?
C27D C28D . 1.391(6) ?
C27D C32D . 1.408(12) ?
C28D C29D . 1.376(6) ?
C28D H28D . 0.950000 ?
C29D C30D . 1.377(10) ?
C29D H29D . 0.950000 ?
C30D C31D . 1.33(2) ?
C30D H30D . 0.950000 ?
C31D C32D . 1.381(17) ?
C31D H31D . 0.950000 ?
C32D H32D . 0.950000 ?
O33 C34 . 1.353(3) ?
C34 O35 . 1.203(3) ?
C34 C36 . 1.489(4) ?
C36 H36A . 0.980000 ?
C36 H36B . 0.980000 ?
C36 H36C . 0.980000 ?
O37 C38 . 1.437(3) ?
C38 C39 . 1.505(3) ?
C38 H38A . 0.990000 ?
C38 H38B . 0.990000 ?
C39 C40 . 1.364(3) ?
C39 C44 . 1.377(3) ?
C40 C41 . 1.387(4) ?
C40 H40 . 0.950000 ?
C41 C42 . 1.359(4) ?
C41 H41 . 0.950000 ?
C42 C43 . 1.364(3) ?
C42 H42 . 0.950000 ?
C43 C44 . 1.375(3) ?
C43 H43 . 0.950000 ?
C44 H44 . 0.950000 ?
O45 H45 . 0.840000 ?
O46 C47 . 1.334(9) ?
O46 C47D . 1.505(7) ?
C47 O48 . 1.415(10) ?
C47 H47A . 0.990000 ?
C47 H47B . 0.990000 ?
O48 C49 . 1.413(6) ?
C49 H49A . 0.980000 ?
C49 H49B . 0.980000 ?
C49 H49C . 0.980000 ?
C47D O48D . 1.391(9) ?
C47D H47D . 0.990000 ?
C47D H47E . 0.990000 ?
O48D C49D . 1.401(7) ?
C49D H49D . 0.980000 ?
C49D H49E . 0.980000 ?
C49D H49F . 0.980000 ?
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
C2 H2 O33 . 1.00 2.44 3.344(3) 149.7 y
O45 H45 O35 2_776 0.84 2.43 3.098(2) 136.9 y
C18 H18C O45 2_776 0.98 2.47 3.442(3) 169.2 y
C38 H38A O24 1_655 0.99 2.48 3.409(3) 156.3 y
C32D H32D O37 1_455 0.95 2.57 3.465(16) 156.5 y
C19 H19A O23 2_675 0.98 2.60 3.560(3) 168.3 y
C16 H16C O33 . 0.98 2.23 2.814(3) 117.4 n
C47D H47D O20 . 0.99 2.55 3.103(9) 115.4 n
C5 H5A O48D . 0.99 2.56 3.147(4) 117.5 n
C38 H38B O23 2_775 0.99 2.61 3.542(3) 156.6 n
C28D H28D Cg2 2_666 0.95 2.93 3.546(7) 124 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O22 C1 C2 O20 . . . . -2.10(19) ?
C14 C1 C2 O20 . . . . -116.91(18) ?
C15 C1 C2 O20 . . . . 113.25(17) ?
O22 C1 C2 C3 . . . . 124.67(18) ?
C14 C1 C2 C3 . . . . 9.9(3) ?
C15 C1 C2 C3 . . . . -120.0(2) ?
O20 C2 C3 C4 . . . . 6.0(3) ?
C1 C2 C3 C4 . . . . -116.7(2) ?
O20 C2 C3 C8 . . . . -122.75(18) ?
C1 C2 C3 C8 . . . . 114.5(2) ?
C2 C3 C4 O46 . . . . 65.1(2) ?
C8 C3 C4 O46 . . . . -169.98(16) ?
C2 C3 C4 C5 . . . . -176.87(19) ?
C8 C3 C4 C5 . . . . -51.9(3) ?
O46 C4 C5 C6 . . . . 165.47(17) ?
C3 C4 C5 C6 . . . . 50.7(3) ?
C4 C5 C6 C7 . . . . -55.6(2) ?
C5 C6 C7 O24 . . . . -177.67(17) ?
C5 C6 C7 C8 . . . . 61.8(2) ?
C4 C3 C8 C19 . . . . -65.4(2) ?
C2 C3 C8 C19 . . . . 61.7(2) ?
C4 C3 C8 C7 . . . . 54.4(2) ?
C2 C3 C8 C7 . . . . -178.56(16) ?
C4 C3 C8 C9 . . . . 168.03(17) ?
C2 C3 C8 C9 . . . . -64.9(2) ?
O24 C7 C8 C19 . . . . -58.7(2) ?
C6 C7 C8 C19 . . . . 62.6(2) ?
O24 C7 C8 C3 . . . . 179.36(15) ?
C6 C7 C8 C3 . . . . -59.3(2) ?
O24 C7 C8 C9 . . . . 60.4(2) ?
C6 C7 C8 C9 . . . . -178.23(18) ?
C19 C8 C9 C10 . . . . -66.7(3) ?
C3 C8 C9 C10 . . . . 61.0(3) ?
C7 C8 C9 C10 . . . . 174.9(2) ?
C8 C9 C10 O33 . . . . 55.6(3) ?
C8 C9 C10 C11 . . . . -77.2(3) ?
O33 C10 C11 C12 . . . . 178.71(16) ?
C9 C10 C11 C12 . . . . -50.4(3) ?
O33 C10 C11 C15 . . . . -46.3(3) ?
C9 C10 C11 C15 . . . . 84.6(3) ?
C10 C11 C12 O45 . . . . -156.12(16) ?
C15 C11 C12 O45 . . . . 65.0(2) ?
C10 C11 C12 C18 . . . . -40.4(2) ?
C15 C11 C12 C18 . . . . -179.31(17) ?
C10 C11 C12 C13 . . . . 84.6(2) ?
C15 C11 C12 C13 . . . . -54.2(2) ?
O45 C12 C13 O37 . . . . 51.0(2) ?
C18 C12 C13 O37 . . . . -64.9(2) ?
C11 C12 C13 O37 . . . . 168.11(16) ?
O45 C12 C13 C14 . . . . -72.1(2) ?
C18 C12 C13 C14 . . . . 171.95(19) ?
C11 C12 C13 C14 . . . . 45.0(2) ?
O22 C1 C14 C13 . . . . 169.91(16) ?
C15 C1 C14 C13 . . . . 52.4(2) ?
C2 C1 C14 C13 . . . . -76.8(2) ?
O37 C13 C14 C1 . . . . -165.42(16) ?
C12 C13 C14 C1 . . . . -45.3(3) ?
O22 C1 C15 C16 . . . . 62.0(2) ?
C14 C1 C15 C16 . . . . 177.37(18) ?
C2 C1 C15 C16 . . . . -49.4(2) ?
O22 C1 C15 C17 . . . . -51.8(2) ?
C14 C1 C15 C17 . . . . 63.6(2) ?
C2 C1 C15 C17 . . . . -163.23(17) ?
O22 C1 C15 C11 . . . . -173.48(17) ?
C14 C1 C15 C11 . . . . -58.1(2) ?
C2 C1 C15 C11 . . . . 75.1(2) ?
C12 C11 C15 C1 . . . . 60.7(2) ?
C10 C11 C15 C1 . . . . -73.2(2) ?
C12 C11 C15 C16 . . . . -175.92(18) ?
C10 C11 C15 C16 . . . . 50.2(3) ?
C12 C11 C15 C17 . . . . -60.1(2) ?
C10 C11 C15 C17 . . . . 166.0(2) ?
C3 C2 O20 C21 . . . . -129.25(18) ?
C1 C2 O20 C21 . . . . 2.2(2) ?
C2 O20 C21 O23 . . . . 179.9(2) ?
C2 O20 C21 O22 . . . . -1.3(2) ?
O23 C21 O22 C1 . . . . 178.5(2) ?
O20 C21 O22 C1 . . . . -0.2(2) ?
C14 C1 O22 C21 . . . . 125.39(18) ?
C15 C1 O22 C21 . . . . -115.1(2) ?
C2 C1 O22 C21 . . . . 1.5(2) ?
C6 C7 O24 C25 . . . . 80.8(3) ?
C8 C7 O24 C25 . . . . -155.6(3) ?
C6 C7 O24 C25D . . . . 124.7(3) ?
C8 C7 O24 C25D . . . . -111.7(3) ?
C7 O24 C25 O26 . . . . 1.9(7) ?
C7 O24 C25 C27 . . . . 176.2(3) ?
O26 C25 C27 C32 . . . . 162.7(10) ?
O24 C25 C27 C32 . . . . -11.8(11) ?
O26 C25 C27 C28 . . . . -13.7(8) ?
O24 C25 C27 C28 . . . . 171.8(4) ?
C32 C27 C28 C29 . . . . 0.6(11) ?
C25 C27 C28 C29 . . . . 177.2(4) ?
C27 C28 C29 C30 . . . . -1.7(8) ?
C28 C29 C30 C31 . . . . 2.5(12) ?
C29 C30 C31 C32 . . . . -2.3(17) ?
C28 C27 C32 C31 . . . . -0.6(18) ?
C25 C27 C32 C31 . . . . -177.0(11) ?
C30 C31 C32 C27 . . . . 1.(2) ?
C7 O24 C25D O26D . . . . -7.1(7) ?
C7 O24 C25D C27D . . . . 177.4(4) ?
O26D C25D C27D C28D . . . . -4.8(9) ?
O24 C25D C27D C28D . . . . 170.5(4) ?
O26D C25D C27D C32D . . . . 171.3(10) ?
O24 C25D C27D C32D . . . . -13.4(11) ?
C32D C27D C28D C29D . . . . 3.3(11) ?
C25D C27D C28D C29D . . . . 179.6(5) ?
C27D C28D C29D C30D . . . . -0.8(8) ?
C28D C29D C30D C31D . . . . 0.0(13) ?
C29D C30D C31D C32D . . . . -2.(2) ?
C30D C31D C32D C27D . . . . 4.(2) ?
C28D C27D C32D C31D . . . . -4.9(18) ?
C25D C27D C32D C31D . . . . 179.0(11) ?
C9 C10 O33 C34 . . . . 133.93(19) ?
C11 C10 O33 C34 . . . . -84.7(2) ?
C10 O33 C34 O35 . . . . 0.5(3) ?
C10 O33 C34 C36 . . . . -178.7(2) ?
C12 C13 O37 C38 . . . . 169.98(16) ?
C14 C13 O37 C38 . . . . -64.8(2) ?
C13 O37 C38 C39 . . . . -60.8(2) ?
O37 C38 C39 C40 . . . . 139.0(2) ?
O37 C38 C39 C44 . . . . -43.6(3) ?
C44 C39 C40 C41 . . . . -1.2(4) ?
C38 C39 C40 C41 . . . . 176.2(2) ?
C39 C40 C41 C42 . . . . 1.5(4) ?
C40 C41 C42 C43 . . . . -0.2(4) ?
C41 C42 C43 C44 . . . . -1.2(4) ?
C42 C43 C44 C39 . . . . 1.5(4) ?
C40 C39 C44 C43 . . . . -0.2(4) ?
C38 C39 C44 C43 . . . . -177.7(2) ?
C3 C4 O46 C47 . . . . -156.2(5) ?
C5 C4 O46 C47 . . . . 85.0(5) ?
C3 C4 O46 C47D . . . . -144.5(4) ?
C5 C4 O46 C47D . . . . 96.7(4) ?
C4 O46 C47 O48 . . . . -79.7(6) ?
O46 C47 O48 C49 . . . . -66.8(7) ?
C4 O46 C47D O48D . . . . -65.8(7) ?
O46 C47D O48D C49D . . . . -64.7(7) ?
