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#$Date: 2020-07-01 02:13:27 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253577 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558449.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_1558449
loop_
_publ_author_name
'Rivera-Chávez, José'
'Bustos-Brito, Celia'
'Aguilar-Ramírez, Enrique'
'Martínez-Otero, Diego'
'Rosales-Vázquez, Luis D.'
'Dorazco-González, Alejandro'
'Cano-Sánchez, Patricia'
_publ_section_title
;
 Hydroxy-neo-Clerodanes and 5,10-seco-neo-Clerodanes from Salvia decora
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00313
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O6, 0.869(C3 H6 O), 0.131(H2 O)'
_chemical_formula_sum            'C22.61 H25.48 O7'
_chemical_formula_weight         409.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.7694(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3816(4)
_cell_length_b                   7.6040(3)
_cell_length_c                   21.7468(7)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      3.81
_cell_volume                     2004.41(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35743
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.060
_diffrn_reflns_theta_min         2.075
_diffrn_source                   'Incoatec ImuS'
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 2830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7010
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0353
_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/[σ²(Fo²)+(0.0688P)²+0.4532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                6951
_reflns_number_total             7010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00313_si_002.cif
_cod_data_source_block           cu_034ERB19_100K_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558449
_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   0.704
_shelx_estimated_absorpt_t_max   0.901
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
O1 O 0.93818(14) 0.3765(3) 0.34706(8) 0.0286(4) Uani 1 1 d D . . . .
H1A H 0.952(3) 0.426(5) 0.3150(11) 0.043 Uiso 1 1 d D U . . .
O2 O 0.70362(14) 0.5695(3) 0.35482(8) 0.0261(4) Uani 1 1 d . . . . .
O3 O 0.74058(15) 0.5636(3) 0.26115(8) 0.0326(4) Uani 1 1 d . . . . .
O4 O 0.5369(2) 0.8099(4) 0.49302(11) 0.0532(6) Uani 1 1 d . . . . .
O5 O 1.18128(15) -0.0554(3) 0.42227(10) 0.0404(5) Uani 1 1 d . . . . .
O6 O 1.01809(15) -0.1523(3) 0.36998(8) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.8061(2) 0.1261(4) 0.47015(11) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.741653 0.151995 0.485827 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9053(2) 0.0698(4) 0.51448(11) 0.0288(5) Uani 1 1 d . . . . .
H2 H 0.900418 0.041444 0.556372 0.035 Uiso 1 1 calc R U . . .
C3 C 1.0016(2) 0.0577(4) 0.49746(12) 0.0284(5) Uani 1 1 d . . . . .
H3 H 1.064694 0.021249 0.527337 0.034 Uiso 1 1 calc R U . . .
C4 C 1.01293(19) 0.1009(4) 0.43129(11) 0.0265(5) Uani 1 1 d . . . . .
H4 H 1.047540 0.219329 0.429928 0.032 Uiso 1 1 calc R U . . .
C5 C 0.90298(19) 0.0907(3) 0.38252(10) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.91273(19) 0.2022(4) 0.32478(11) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.974153 0.155854 0.305840 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8059(2) 0.2013(4) 0.27562(10) 0.0279(5) Uani 1 1 d . . . . .
H7A H 0.787056 0.079010 0.261928 0.034 Uiso 1 1 calc R U . . .
H7AB H 0.816139 0.269736 0.238489 0.034 Uiso 1 1 calc R U . . .
C8 C 0.71168(18) 0.2807(4) 0.30197(10) 0.0242(5) Uani 1 1 d . . . . .
H8 H 0.643273 0.257076 0.269691 0.029 Uiso 1 1 calc R U . . .
C9 C 0.69429(18) 0.1870(3) 0.36237(10) 0.0223(5) Uani 1 1 d . . . . .
C10 C 0.80207(18) 0.1426(3) 0.40847(10) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.61909(18) 0.3086(3) 0.39107(11) 0.0238(5) Uani 1 1 d . . . . .
H11A H 0.549079 0.326449 0.360342 0.029 Uiso 1 1 calc R U . . .
H11B H 0.601389 0.251663 0.428750 0.029 Uiso 1 1 calc R U . . .
C12 C 0.67193(18) 0.4842(3) 0.40919(10) 0.0231(5) Uani 1 1 d . . . . .
H12 H 0.739605 0.466030 0.442570 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5978(2) 0.6113(4) 0.43273(11) 0.0262(5) Uani 1 1 d . . . . .
C14 C 0.4866(2) 0.6576(4) 0.40430(13) 0.0342(6) Uani 1 1 d . . . . .
H14 H 0.444161 0.613092 0.366099 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4544(3) 0.7767(4) 0.44265(15) 0.0428(7) Uani 1 1 d . . . . .
H15 H 0.383651 0.830432 0.435524 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6237(3) 0.7066(5) 0.48555(13) 0.0416(7) Uani 1 1 d . . . . .
H16 H 0.692954 0.702778 0.513967 0.050 Uiso 1 1 calc R U . . .
C17 C 0.72270(18) 0.4788(4) 0.30535(11) 0.0247(5) Uani 1 1 d . . . . .
C18 C 1.0828(2) -0.0395(4) 0.40864(12) 0.0309(6) Uani 1 1 d . . . . .
C19 C 0.9027(2) -0.1076(4) 0.36632(11) 0.0280(5) Uani 1 1 d . . . . .
H19A H 0.871173 -0.177612 0.396791 0.034 Uiso 1 1 calc R U . . .
H19B H 0.858971 -0.129672 0.323571 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6324(2) 0.0141(4) 0.34401(13) 0.0323(6) Uani 1 1 d . . . . .
H20A H 0.560667 0.039268 0.316798 0.048 Uiso 1 1 calc R U . . .
H20B H 0.621105 -0.046466 0.381971 0.048 Uiso 1 1 calc R U . . .
H20C H 0.675740 -0.060898 0.321513 0.048 Uiso 1 1 calc R U . . .
O1' O 0.56394(13) 0.5865(2) 0.15073(7) 0.0241(3) Uani 1 1 d D . . . .
H1A' H 0.608(2) 0.534(4) 0.1792(11) 0.036 Uiso 1 1 d D U . . .
O2' O 0.31825(13) 0.3796(3) 0.14876(8) 0.0268(4) Uani 1 1 d . . . . .
O3' O 0.44001(15) 0.3835(3) 0.23659(8) 0.0324(4) Uani 1 1 d . . . . .
O4' O 0.03409(16) 0.1740(3) 0.00754(9) 0.0434(5) Uani 1 1 d . . . . .
O5' O 0.73915(14) 1.0196(3) 0.07626(9) 0.0343(4) Uani 1 1 d . . . . .
O6' O 0.61456(13) 1.1147(3) 0.12983(8) 0.0282(4) Uani 1 1 d . . . . .
C1' C 0.32819(19) 0.8312(3) 0.03352(11) 0.0240(5) Uani 1 1 d . . . . .
H1' H 0.252688 0.801656 0.019218 0.029 Uiso 1 1 calc R U . . .
C2' C 0.39044(19) 0.8939(4) -0.01209(10) 0.0257(5) Uani 1 1 d . . . . .
H2' H 0.352082 0.923176 -0.053238 0.031 Uiso 1 1 calc R U . . .
C3' C 0.4997(2) 0.9112(3) 0.00227(11) 0.0253(5) Uani 1 1 d . . . . .
H3' H 0.537924 0.953305 -0.028493 0.030 Uiso 1 1 calc R U . . .
C4' C 0.56327(17) 0.8647(4) 0.06697(10) 0.0226(5) Uani 1 1 d . . . . .
H4' H 0.598732 0.746732 0.066355 0.027 Uiso 1 1 calc R U . . .
C5' C 0.49237(17) 0.8693(3) 0.11774(10) 0.0194(4) Uani 1 1 d . . . . .
C6' C 0.55008(18) 0.7588(3) 0.17414(10) 0.0212(4) Uani 1 1 d . . . . .
H6' H 0.624140 0.810627 0.191770 0.025 Uiso 1 1 calc R U . . .
C7' C 0.48263(18) 0.7504(3) 0.22562(10) 0.0228(5) Uani 1 1 d . . . . .
H7'A H 0.523255 0.680537 0.261366 0.027 Uiso 1 1 calc R U . . .
H7'B H 0.472824 0.870748 0.240971 0.027 Uiso 1 1 calc R U . . .
C8' C 0.36971(18) 0.6674(3) 0.20145(10) 0.0215(5) Uani 1 1 d . . . . .
H8' H 0.327479 0.685931 0.235519 0.026 Uiso 1 1 calc R U . . .
C9' C 0.30323(17) 0.7643(3) 0.14327(10) 0.0212(5) Uani 1 1 d . . . . .
C10' C 0.37247(17) 0.8131(3) 0.09482(10) 0.0201(4) Uani 1 1 d . . . . .
C11' C 0.20617(17) 0.6434(3) 0.11664(11) 0.0223(5) Uani 1 1 d . . . . .
H11C H 0.161517 0.624026 0.148964 0.027 Uiso 1 1 calc R U . . .
H11D H 0.158557 0.701230 0.080141 0.027 Uiso 1 1 calc R U . . .
C12' C 0.24446(17) 0.4682(3) 0.09642(11) 0.0221(5) Uani 1 1 d . . . . .
H12' H 0.285616 0.488530 0.061986 0.026 Uiso 1 1 calc R U . . .
C13' C 0.15170(18) 0.3434(3) 0.07325(11) 0.0238(5) Uani 1 1 d . . . . .
C14' C 0.06725(19) 0.2834(4) 0.10460(13) 0.0291(5) Uani 1 1 d . . . . .
H14' H 0.060547 0.309735 0.146359 0.035 Uiso 1 1 calc R U . . .
C15' C -0.0005(2) 0.1823(4) 0.06282(13) 0.0353(6) Uani 1 1 d . . . . .
H15' H -0.064173 0.124446 0.070929 0.042 Uiso 1 1 calc R U . . .
C16' C 0.1272(2) 0.2744(4) 0.01535(13) 0.0350(6) Uani 1 1 d . . . . .
H16' H 0.169143 0.293012 -0.016104 0.042 Uiso 1 1 calc R U . . .
C17' C 0.38107(18) 0.4685(4) 0.19601(11) 0.0234(5) Uani 1 1 d . . . . .
C18' C 0.65022(19) 1.0037(4) 0.08989(11) 0.0269(5) Uani 1 1 d . . . . .
C19' C 0.50266(18) 1.0667(3) 0.13500(11) 0.0239(5) Uani 1 1 d . . . . .
H19C H 0.447625 1.136859 0.105594 0.029 Uiso 1 1 calc R U . . .
H19D H 0.491521 1.086056 0.178291 0.029 Uiso 1 1 calc R U . . .
C20' C 0.2562(2) 0.9361(4) 0.16478(13) 0.0288(5) Uani 1 1 d . . . . .
H20D H 0.211569 0.995828 0.128359 0.043 Uiso 1 1 calc R U . . .
H20E H 0.316988 1.012846 0.184503 0.043 Uiso 1 1 calc R U . . .
H20F H 0.209994 0.908695 0.195156 0.043 Uiso 1 1 calc R U . . .
O7' O 0.98521(17) 0.5307(3) 0.23313(10) 0.0541(7) Uani 1 1 d D . . . .
C21' C 0.8543(2) 0.5563(4) 0.13789(12) 0.0405(7) Uani 1 1 d D . . . .
H21A H 0.787416 0.628702 0.130115 0.061 Uiso 1 1 calc R U . . .
H21B H 0.835272 0.435106 0.146698 0.061 Uiso 1 1 calc R U . . .
H21C H 0.887680 0.558171 0.100723 0.061 Uiso 1 1 calc R U . . .
C22' C 0.9346(2) 0.6281(4) 0.19306(11) 0.0379(7) Uani 1 1 d D . . . .
C23' C 0.9526(3) 0.8210(4) 0.19500(17) 0.0544(9) Uani 1 1 d D . . . .
H23A H 0.980935 0.857462 0.158058 0.082 Uiso 1 1 calc R U . . .
H23B H 1.006153 0.851939 0.233195 0.082 Uiso 1 1 calc R U . . .
H23C H 0.882580 0.881101 0.195026 0.082 Uiso 1 1 calc R U . . .
O7 O 1.1411(2) 0.1348(5) 0.27308(15) 0.0619(11) Uani 0.738(5) 1 d D U P A 1
C21 C 1.2212(3) 0.3837(5) 0.3299(2) 0.0567(12) Uani 0.738(5) 1 d D U P A 1
H21D H 1.284020 0.448232 0.320015 0.085 Uiso 0.738(5) 1 calc R U P A 1
H21E H 1.226368 0.382795 0.375443 0.085 Uiso 0.738(5) 1 calc R U P A 1
H21F H 1.152339 0.441248 0.309443 0.085 Uiso 0.738(5) 1 calc R U P A 1
C22 C 1.2223(2) 0.1988(5) 0.30653(17) 0.0465(10) Uani 0.738(5) 1 d D U P A 1
C23 C 1.3259(3) 0.0977(6) 0.32669(18) 0.0479(11) Uani 0.738(5) 1 d D U P A 1
H23D H 1.355241 0.118347 0.371466 0.072 Uiso 0.738(5) 1 calc R U P A 1
H23E H 1.380173 0.135923 0.302358 0.072 Uiso 0.738(5) 1 calc R U P A 1
H23F H 1.310841 -0.027972 0.319562 0.072 Uiso 0.738(5) 1 calc R U P A 1
O8 O 1.2075(11) 0.656(3) 0.3161(7) 0.104(6) Uani 0.262(5) 1 d D U P A 2
H8A H 1.22(2) 0.569(17) 0.340(8) 0.124 Uiso 0.262(5) 1 d D U P A 2
H8B H 1.162(7) 0.63(3) 0.2826(19) 0.124 Uiso 0.262(5) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1A 102(3) . . ?
C17 O2 C12 122.6(2) . . ?
C15 O4 C16 106.1(2) . . ?
C18 O6 C19 109.75(19) . . ?
C10 C1 C2 122.9(2) . . ?
C10 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C18 109.0(2) . . ?
C3 C4 C5 113.7(2) . . ?
C18 C4 C5 102.82(19) . . ?
C3 C4 H4 110.3 . . ?
C18 C4 H4 110.3 . . ?
C5 C4 H4 110.3 . . ?
C10 C5 C6 111.44(19) . . ?
C10 C5 C4 113.96(19) . . ?
C6 C5 C4 109.06(19) . . ?
C10 C5 C19 111.9(2) . . ?
C6 C5 C19 110.35(19) . . ?
C4 C5 C19 99.57(19) . . ?
O1 C6 C7 110.1(2) . . ?
O1 C6 C5 106.48(18) . . ?
C7 C6 C5 111.6(2) . . ?
O1 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
C6 C7 C8 110.86(19) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
C8 C7 H7AB 109.5 . . ?
H7A C7 H7AB 108.1 . . ?
C17 C8 C7 110.1(2) . . ?
C17 C8 C9 116.4(2) . . ?
C7 C8 C9 112.71(19) . . ?
C17 C8 H8 105.6 . . ?
C7 C8 H8 105.6 . . ?
C9 C8 H8 105.6 . . ?
C11 C9 C20 108.07(19) . . ?
C11 C9 C10 112.72(18) . . ?
C20 C9 C10 107.7(2) . . ?
C11 C9 C8 105.62(19) . . ?
C20 C9 C8 108.82(19) . . ?
C10 C9 C8 113.76(18) . . ?
C1 C10 C5 118.8(2) . . ?
C1 C10 C9 121.7(2) . . ?
C5 C10 C9 118.98(19) . . ?
C12 C11 C9 111.98(18) . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O2 C12 C13 105.87(19) . . ?
O2 C12 C11 110.76(18) . . ?
C13 C12 C11 113.54(19) . . ?
O2 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C16 C13 C14 106.1(2) . . ?
C16 C13 C12 125.9(2) . . ?
C14 C13 C12 127.9(2) . . ?
C15 C14 C13 106.1(3) . . ?
C15 C14 H14 126.9 . . ?
C13 C14 H14 126.9 . . ?
C14 C15 O4 110.8(3) . . ?
C14 C15 H15 124.6 . . ?
O4 C15 H15 124.6 . . ?
C13 C16 O4 110.9(3) . . ?
C13 C16 H16 124.6 . . ?
O4 C16 H16 124.6 . . ?
O3 C17 O2 116.9(2) . . ?
O3 C17 C8 121.3(2) . . ?
O2 C17 C8 121.5(2) . . ?
O5 C18 O6 122.4(3) . . ?
O5 C18 C4 127.4(3) . . ?
O6 C18 C4 110.2(2) . . ?
O6 C19 C5 105.0(2) . . ?
O6 C19 H19A 110.8 . . ?
C5 C19 H19A 110.8 . . ?
O6 C19 H19B 110.8 . . ?
C5 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6' O1' H1A' 106(2) . . ?
C17' O2' C12' 122.36(19) . . ?
C15' O4' C16' 106.0(2) . . ?
C18' O6' C19' 109.50(18) . . ?
C10' C1' C2' 123.0(2) . . ?
C10' C1' H1' 118.5 . . ?
C2' C1' H1' 118.5 . . ?
C3' C2' C1' 121.8(2) . . ?
C3' C2' H2' 119.1 . . ?
C1' C2' H2' 119.1 . . ?
C2' C3' C4' 120.5(2) . . ?
C2' C3' H3' 119.8 . . ?
C4' C3' H3' 119.8 . . ?
C3' C4' C18' 110.1(2) . . ?
C3' C4' C5' 113.41(18) . . ?
C18' C4' C5' 102.58(18) . . ?
C3' C4' H4' 110.2 . . ?
C18' C4' H4' 110.2 . . ?
C5' C4' H4' 110.2 . . ?
C10' C5' C6' 111.72(19) . . ?
C10' C5' C4' 114.62(17) . . ?
C6' C5' C4' 108.57(17) . . ?
C10' C5' C19' 112.16(18) . . ?
C6' C5' C19' 109.59(17) . . ?
C4' C5' C19' 99.49(19) . . ?
O1' C6' C7' 110.26(19) . . ?
O1' C6' C5' 106.69(16) . . ?
C7' C6' C5' 111.88(18) . . ?
O1' C6' H6' 109.3 . . ?
C7' C6' H6' 109.3 . . ?
C5' C6' H6' 109.3 . . ?
C8' C7' C6' 111.35(17) . . ?
C8' C7' H7'A 109.4 . . ?
C6' C7' H7'A 109.4 . . ?
C8' C7' H7'B 109.4 . . ?
C6' C7' H7'B 109.4 . . ?
H7'A C7' H7'B 108.0 . . ?
C17' C8' C7' 110.13(19) . . ?
C17' C8' C9' 116.76(19) . . ?
C7' C8' C9' 112.44(19) . . ?
C17' C8' H8' 105.5 . . ?
C7' C8' H8' 105.5 . . ?
C9' C8' H8' 105.5 . . ?
C11' C9' C10' 113.05(18) . . ?
C11' C9' C20' 107.91(18) . . ?
C10' C9' C20' 107.59(19) . . ?
C11' C9' C8' 105.62(19) . . ?
C10' C9' C8' 113.48(17) . . ?
C20' C9' C8' 109.03(19) . . ?
C1' C10' C5' 118.0(2) . . ?
C1' C10' C9' 122.36(19) . . ?
C5' C10' C9' 119.07(18) . . ?
C12' C11' C9' 111.81(17) . . ?
C12' C11' H11C 109.3 . . ?
C9' C11' H11C 109.3 . . ?
C12' C11' H11D 109.3 . . ?
C9' C11' H11D 109.3 . . ?
H11C C11' H11D 107.9 . . ?
O2' C12' C13' 106.48(19) . . ?
O2' C12' C11' 111.19(18) . . ?
C13' C12' C11' 113.12(18) . . ?
O2' C12' H12' 108.6 . . ?
C13' C12' H12' 108.6 . . ?
C11' C12' H12' 108.6 . . ?
C16' C13' C14' 105.9(2) . . ?
C16' C13' C12' 125.2(2) . . ?
C14' C13' C12' 128.7(2) . . ?
C15' C14' C13' 106.0(2) . . ?
C15' C14' H14' 127.0 . . ?
C13' C14' H14' 127.0 . . ?
C14' C15' O4' 111.0(2) . . ?
C14' C15' H15' 124.5 . . ?
O4' C15' H15' 124.5 . . ?
C13' C16' O4' 111.1(2) . . ?
C13' C16' H16' 124.5 . . ?
O4' C16' H16' 124.5 . . ?
O3' C17' O2' 117.4(2) . . ?
O3' C17' C8' 121.6(2) . . ?
O2' C17' C8' 120.8(2) . . ?
O5' C18' O6' 122.1(2) . . ?
O5' C18' C4' 127.7(3) . . ?
O6' C18' C4' 110.11(19) . . ?
O6' C19' C5' 104.88(18) . . ?
O6' C19' H19C 110.8 . . ?
C5' C19' H19C 110.8 . . ?
O6' C19' H19D 110.8 . . ?
C5' C19' H19D 110.8 . . ?
H19C C19' H19D 108.8 . . ?
C9' C20' H20D 109.5 . . ?
C9' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C9' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C22' C21' H21A 109.5 . . ?
C22' C21' H21B 109.5 . . ?
H21A C21' H21B 109.5 . . ?
C22' C21' H21C 109.5 . . ?
H21A C21' H21C 109.5 . . ?
H21B C21' H21C 109.5 . . ?
O7' C22' C23' 122.0(3) . . ?
O7' C22' C21' 120.9(3) . . ?
C23' C22' C21' 117.1(2) . . ?
C22' C23' H23A 109.5 . . ?
C22' C23' H23B 109.5 . . ?
H23A C23' H23B 109.5 . . ?
C22' C23' H23C 109.5 . . ?
H23A C23' H23C 109.5 . . ?
H23B C23' H23C 109.5 . . ?
C22 C21 H21D 109.5 . . ?
C22 C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
C22 C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
O7 C22 C23 121.9(3) . . ?
O7 C22 C21 121.0(3) . . ?
C23 C22 C21 117.0(2) . . ?
C22 C23 H23D 109.5 . . ?
C22 C23 H23E 109.5 . . ?
H23D C23 H23E 109.5 . . ?
C22 C23 H23F 109.5 . . ?
H23D C23 H23F 109.5 . . ?
H23E C23 H23F 109.5 . . ?
H8A O8 H8B 113(3) . . ?
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
O1 C6 1.424(3) . ?
O1 H1A 0.838(11) . ?
O2 C17 1.339(3) . ?
O2 C12 1.470(3) . ?
O3 C17 1.215(3) . ?
O4 C15 1.361(4) . ?
O4 C16 1.367(4) . ?
O5 C18 1.201(3) . ?
O6 C18 1.345(3) . ?
O6 C19 1.455(3) . ?
C1 C10 1.338(3) . ?
C1 C2 1.462(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.322(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.510(3) . ?
C3 H3 0.9500 . ?
C4 C18 1.518(4) . ?
C4 C5 1.548(3) . ?
C4 H4 1.0000 . ?
C5 C10 1.524(3) . ?
C5 C6 1.541(3) . ?
C5 C19 1.548(4) . ?
C6 C7 1.522(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C17 1.513(4) . ?
C8 C9 1.547(3) . ?
C8 H8 1.0000 . ?
C9 C11 1.532(3) . ?
C9 C20 1.533(3) . ?
C9 C10 1.534(3) . ?
C11 C12 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.494(3) . ?
C12 H12 1.0000 . ?
C13 C16 1.341(4) . ?
C13 C14 1.433(4) . ?
C14 C15 1.346(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1' C6' 1.428(3) . ?
O1' H1A' 0.837(11) . ?
O2' C17' 1.338(3) . ?
O2' C12' 1.470(3) . ?
O3' C17' 1.211(3) . ?
O4' C15' 1.358(4) . ?
O4' C16' 1.364(3) . ?
O5' C18' 1.203(3) . ?
O6' C18' 1.348(3) . ?
O6' C19' 1.459(3) . ?
C1' C10' 1.341(3) . ?
C1' C2' 1.455(3) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.332(4) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.508(3) . ?
C3' H3' 0.9500 . ?
C4' C18' 1.519(3) . ?
C4' C5' 1.545(3) . ?
C4' H4' 1.0000 . ?
C5' C10' 1.527(3) . ?
C5' C6' 1.537(3) . ?
C5' C19' 1.546(3) . ?
C6' C7' 1.528(3) . ?
C6' H6' 1.0000 . ?
C7' C8' 1.526(3) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' C17' 1.526(3) . ?
C8' C9' 1.548(3) . ?
C8' H8' 1.0000 . ?
C9' C11' 1.530(3) . ?
C9' C10' 1.533(3) . ?
C9' C20' 1.541(3) . ?
C11' C12' 1.509(3) . ?
C11' H11C 0.9900 . ?
C11' H11D 0.9900 . ?
C12' C13' 1.495(3) . ?
C12' H12' 1.0000 . ?
C13' C16' 1.341(4) . ?
C13' C14' 1.434(3) . ?
C14' C15' 1.345(4) . ?
C14' H14' 0.9500 . ?
C15' H15' 0.9500 . ?
C16' H16' 0.9500 . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
O7' C22' 1.216(3) . ?
C21' C22' 1.496(4) . ?
C21' H21A 0.9800 . ?
C21' H21B 0.9800 . ?
C21' H21C 0.9800 . ?
C22' C23' 1.483(4) . ?
C23' H23A 0.9800 . ?
C23' H23B 0.9800 . ?
C23' H23C 0.9800 . ?
O7 C22 1.216(3) . ?
C21 C22 1.496(4) . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C22 C23 1.483(4) . ?
C23 H23D 0.9800 . ?
C23 H23E 0.9800 . ?
C23 H23F 0.9800 . ?
O8 H8A 0.842(14) . ?
O8 H8B 0.842(14) . ?
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
O1 H1A O7' 0.838(11) 2.068(12) 2.905(3) 176(4) . yes
O1' H1A' O3 0.837(11) 2.18(2) 2.905(2) 145(3) . yes
O8 H8B O7' 0.842(14) 2.37(3) 3.117(14) 148(6) . 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
C10 C1 C2 C3 10.4(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C18 -135.5(3) . . . . ?
C2 C3 C4 C5 -21.5(4) . . . . ?
C3 C4 C5 C10 32.9(3) . . . . ?
C18 C4 C5 C10 150.6(2) . . . . ?
C3 C4 C5 C6 158.2(2) . . . . ?
C18 C4 C5 C6 -84.1(2) . . . . ?
C3 C4 C5 C19 -86.3(2) . . . . ?
C18 C4 C5 C19 31.4(2) . . . . ?
C10 C5 C6 O1 68.3(2) . . . . ?
C4 C5 C6 O1 -58.4(2) . . . . ?
C19 C5 C6 O1 -166.75(18) . . . . ?
C10 C5 C6 C7 -51.9(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C19 C5 C6 C7 73.1(2) . . . . ?
O1 C6 C7 C8 -56.4(3) . . . . ?
C5 C6 C7 C8 61.6(3) . . . . ?
C6 C7 C8 C17 75.6(3) . . . . ?
C6 C7 C8 C9 -56.1(3) . . . . ?
C17 C8 C9 C11 37.6(3) . . . . ?
C7 C8 C9 C11 166.19(19) . . . . ?
C17 C8 C9 C20 153.4(2) . . . . ?
C7 C8 C9 C20 -78.0(2) . . . . ?
C17 C8 C9 C10 -86.6(2) . . . . ?
C7 C8 C9 C10 42.0(3) . . . . ?
C2 C1 C10 C5 3.6(4) . . . . ?
C2 C1 C10 C9 174.8(2) . . . . ?
C6 C5 C10 C1 -149.1(2) . . . . ?
C4 C5 C10 C1 -25.1(3) . . . . ?
C19 C5 C10 C1 86.8(3) . . . . ?
C6 C5 C10 C9 39.5(3) . . . . ?
C4 C5 C10 C9 163.4(2) . . . . ?
C19 C5 C10 C9 -84.6(3) . . . . ?
C11 C9 C10 C1 33.7(3) . . . . ?
C20 C9 C10 C1 -85.4(3) . . . . ?
C8 C9 C10 C1 153.9(2) . . . . ?
C11 C9 C10 C5 -155.1(2) . . . . ?
C20 C9 C10 C5 85.8(3) . . . . ?
C8 C9 C10 C5 -34.9(3) . . . . ?
C20 C9 C11 C12 -178.59(19) . . . . ?
C10 C9 C11 C12 62.5(3) . . . . ?
C8 C9 C11 C12 -62.3(2) . . . . ?
C17 O2 C12 C13 -147.4(2) . . . . ?
C17 O2 C12 C11 -23.9(3) . . . . ?
C9 C11 C12 O2 56.5(2) . . . . ?
C9 C11 C12 C13 175.50(19) . . . . ?
O2 C12 C13 C16 -107.5(3) . . . . ?
C11 C12 C13 C16 130.8(3) . . . . ?
O2 C12 C13 C14 72.1(3) . . . . ?
C11 C12 C13 C14 -49.6(3) . . . . ?
C16 C13 C14 C15 -0.3(3) . . . . ?
C12 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 O4 0.3(3) . . . . ?
C16 O4 C15 C14 -0.1(4) . . . . ?
C14 C13 C16 O4 0.2(3) . . . . ?
C12 C13 C16 O4 179.9(2) . . . . ?
C15 O4 C16 C13 -0.1(4) . . . . ?
C12 O2 C17 O3 174.86(19) . . . . ?
C12 O2 C17 C8 0.6(3) . . . . ?
C7 C8 C17 O3 47.4(3) . . . . ?
C9 C8 C17 O3 177.3(2) . . . . ?
C7 C8 C17 O2 -138.5(2) . . . . ?
C9 C8 C17 O2 -8.7(3) . . . . ?
C19 O6 C18 O5 175.5(2) . . . . ?
C19 O6 C18 C4 -3.6(3) . . . . ?
C3 C4 C18 O5 -77.1(3) . . . . ?
C5 C4 C18 O5 162.0(3) . . . . ?
C3 C4 C18 O6 102.0(2) . . . . ?
C5 C4 C18 O6 -18.9(3) . . . . ?
C18 O6 C19 C5 25.0(2) . . . . ?
C10 C5 C19 O6 -155.23(18) . . . . ?
C6 C5 C19 O6 80.1(2) . . . . ?
C4 C5 C19 O6 -34.5(2) . . . . ?
C10' C1' C2' C3' 10.8(4) . . . . ?
C1' C2' C3' C4' 0.4(4) . . . . ?
C2' C3' C4' C18' -136.8(3) . . . . ?
C2' C3' C4' C5' -22.6(4) . . . . ?
C3' C4' C5' C10' 34.0(3) . . . . ?
C18' C4' C5' C10' 152.6(2) . . . . ?
C3' C4' C5' C6' 159.6(2) . . . . ?
C18' C4' C5' C6' -81.7(2) . . . . ?
C3' C4' C5' C19' -85.9(2) . . . . ?
C18' C4' C5' C19' 32.8(2) . . . . ?
C10' C5' C6' O1' 70.3(2) . . . . ?
C4' C5' C6' O1' -57.0(2) . . . . ?
C19' C5' C6' O1' -164.74(17) . . . . ?
C10' C5' C6' C7' -50.3(2) . . . . ?
C4' C5' C6' C7' -177.69(19) . . . . ?
C19' C5' C6' C7' 74.6(2) . . . . ?
O1' C6' C7' C8' -58.3(2) . . . . ?
C5' C6' C7' C8' 60.3(3) . . . . ?
C6' C7' C8' C17' 75.9(2) . . . . ?
C6' C7' C8' C9' -56.2(3) . . . . ?
C17' C8' C9' C11' 39.0(2) . . . . ?
C7' C8' C9' C11' 167.68(18) . . . . ?
C17' C8' C9' C10' -85.4(2) . . . . ?
C7' C8' C9' C10' 43.3(3) . . . . ?
C17' C8' C9' C20' 154.72(19) . . . . ?
C7' C8' C9' C20' -76.6(2) . . . . ?
C2' C1' C10' C5' 2.9(4) . . . . ?
C2' C1' C10' C9' 173.9(2) . . . . ?
C6' C5' C10' C1' -149.2(2) . . . . ?
C4' C5' C10' C1' -25.2(3) . . . . ?
C19' C5' C10' C1' 87.3(3) . . . . ?
C6' C5' C10' C9' 39.5(3) . . . . ?
C4' C5' C10' C9' 163.5(2) . . . . ?
C19' C5' C10' C9' -84.0(2) . . . . ?
C11' C9' C10' C1' 32.6(3) . . . . ?
C20' C9' C10' C1' -86.4(3) . . . . ?
C8' C9' C10' C1' 152.9(2) . . . . ?
C11' C9' C10' C5' -156.5(2) . . . . ?
C20' C9' C10' C5' 84.5(2) . . . . ?
C8' C9' C10' C5' -36.2(3) . . . . ?
C10' C9' C11' C12' 63.2(2) . . . . ?
C20' C9' C11' C12' -177.89(19) . . . . ?
C8' C9' C11' C12' -61.4(2) . . . . ?
C17' O2' C12' C13' -151.7(2) . . . . ?
C17' O2' C12' C11' -28.1(3) . . . . ?
C9' C11' C12' O2' 57.2(2) . . . . ?
C9' C11' C12' C13' 177.00(19) . . . . ?
O2' C12' C13' C16' -118.2(3) . . . . ?
C11' C12' C13' C16' 119.4(3) . . . . ?
O2' C12' C13' C14' 66.9(3) . . . . ?
C11' C12' C13' C14' -55.5(3) . . . . ?
C16' C13' C14' C15' 0.4(3) . . . . ?
C12' C13' C14' C15' 176.0(2) . . . . ?
C13' C14' C15' O4' -0.2(3) . . . . ?
C16' O4' C15' C14' -0.1(3) . . . . ?
C14' C13' C16' O4' -0.5(3) . . . . ?
C12' C13' C16' O4' -176.3(2) . . . . ?
C15' O4' C16' C13' 0.4(3) . . . . ?
C12' O2' C17' O3' -179.2(2) . . . . ?
C12' O2' C17' C8' 6.7(3) . . . . ?
C7' C8' C17' O3' 43.1(3) . . . . ?
C9' C8' C17' O3' 172.9(2) . . . . ?
C7' C8' C17' O2' -143.1(2) . . . . ?
C9' C8' C17' O2' -13.3(3) . . . . ?
C19' O6' C18' O5' 177.6(2) . . . . ?
C19' O6' C18' C4' -2.4(3) . . . . ?
C3' C4' C18' O5' -79.6(3) . . . . ?
C5' C4' C18' O5' 159.4(3) . . . . ?
C3' C4' C18' O6' 100.4(2) . . . . ?
C5' C4' C18' O6' -20.6(2) . . . . ?
C18' O6' C19' C5' 24.6(2) . . . . ?
C10' C5' C19' O6' -156.84(17) . . . . ?
C6' C5' C19' O6' 78.5(2) . . . . ?
C4' C5' C19' O6' -35.2(2) . . . . ?
