#------------------------------------------------------------------------------
#$Date: 2020-08-04 05:16:32 +0300 (Tue, 04 Aug 2020) $
#$Revision: 254774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558528.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_1558528
loop_
_publ_author_name
'Li, Hao'
'Liang, Yu-Ru'
'Chen, Shao-Xin'
'Wang, Wen-Xuan'
'Zou, Yike'
'Nuryyeva, Selbi'
'Houk, K. N.'
'Xiong, Juan'
'Hu, Jin-Feng'
_publ_section_title
;
 Amentotaxins C-V, Structurally Diverse Diterpenoids from the Leaves and
 Twigs of the Vulnerable Conifer Amentotaxus argotaenia and Their
 Cytotoxic Effects.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2129
_journal_page_last               2144
_journal_paper_doi               10.1021/acs.jnatprod.0c00064
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H26 O3, 0.5(C H4 O)'
_chemical_formula_sum            'C19.5 H28 O3.5'
_chemical_formula_weight         318.42
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7321(3)
_cell_length_b                   13.4089(6)
_cell_length_c                   37.6911(17)
_cell_measurement_reflns_used    7457
_cell_measurement_temperature    296
_cell_measurement_theta_max      53.597
_cell_measurement_theta_min      7.696
_cell_volume                     3402.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            32055
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.823
_diffrn_reflns_theta_min         3.043
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0901 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.7952. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0770P)²+0.3752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5593
_reflns_number_total             6427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00064_si_002.cif
_cod_data_source_block           mjr17096_0m
_cod_depositor_comments
'Adding full bibliography for 1558526--1558528.cif.'
_cod_original_formula_sum        'C19.50 H28 O3.50'
_cod_database_code               1558528
_shelx_shelxl_version_number     2017/1
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C13(H13), C3A(H3A), C5A(H5A), C9A(H9A), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C18(H18A,H18B), C1A(H1AB,H1AC), C2A(H2AA,H2AB),
 C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11C,H11D), C12A(H12C,H12D), C14A(H14C,
 H14D), C18A(H18C,H18D)
2.c Tetrahedral OH refined with riding coordinates:
 O1S(H1S)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C1S(H1SA,H1SB,H1SC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1AA)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.7055(5) 0.5457(2) 0.76574(7) 0.0913(8) Uani 1 1 d . . . . .
H1 H 0.664162 0.488247 0.766765 0.137 Uiso 1 1 calc GR . . . .
O2 O 0.6806(4) 0.41308(19) 0.70788(7) 0.0873(8) Uani 1 1 d . . . . .
O3 O 0.5039(3) 0.6769(2) 0.55388(6) 0.0724(6) Uani 1 1 d . . . . .
C1 C 0.4739(5) 0.7152(2) 0.69712(8) 0.0578(7) Uani 1 1 d . . . . .
H1A H 0.591568 0.742184 0.685791 0.069 Uiso 1 1 calc R . . . .
H1B H 0.379875 0.769408 0.700139 0.069 Uiso 1 1 calc R . . . .
C2 C 0.5305(5) 0.6744(3) 0.73358(8) 0.0661(8) Uani 1 1 d . . . . .
H2A H 0.595463 0.726611 0.747109 0.079 Uiso 1 1 calc R . . . .
H2B H 0.410706 0.655466 0.746186 0.079 Uiso 1 1 calc R . . . .
C3 C 0.6661(5) 0.5859(3) 0.73125(8) 0.0640(8) Uani 1 1 d . . . . .
H3 H 0.792436 0.608118 0.721028 0.077 Uiso 1 1 calc R . . . .
C4 C 0.5797(4) 0.5082(2) 0.70721(8) 0.0569(7) Uani 1 1 d . . . . .
C5 C 0.5336(4) 0.5486(2) 0.67042(7) 0.0490(6) Uani 1 1 d . . . . .
H5 H 0.657354 0.578754 0.661898 0.059 Uiso 1 1 calc R . . . .
C6 C 0.4775(5) 0.4703(2) 0.64294(8) 0.0603(7) Uani 1 1 d . . . . .
H6A H 0.574496 0.416775 0.643155 0.072 Uiso 1 1 calc R . . . .
H6B H 0.348745 0.442173 0.648701 0.072 Uiso 1 1 calc R . . . .
C7 C 0.4704(5) 0.5175(2) 0.60631(8) 0.0581(7) Uani 1 1 d . . . . .
H7A H 0.601917 0.541582 0.600199 0.070 Uiso 1 1 calc R . . . .
H7B H 0.433748 0.467043 0.589075 0.070 Uiso 1 1 calc R . . . .
C8 C 0.3243(4) 0.6034(2) 0.60395(7) 0.0486(6) Uani 1 1 d . . . . .
C9 C 0.3590(4) 0.68085(18) 0.63480(7) 0.0435(5) Uani 1 1 d . . . . .
H9 H 0.488908 0.710516 0.629705 0.052 Uiso 1 1 calc R . . . .
C10 C 0.3808(4) 0.63499(19) 0.67258(7) 0.0453(6) Uani 1 1 d . . . . .
C11 C 0.2097(4) 0.7690(2) 0.63198(8) 0.0537(6) Uani 1 1 d . . . . .
H11A H 0.197544 0.799460 0.655214 0.064 Uiso 1 1 calc R . . . .
H11B H 0.265627 0.818647 0.616154 0.064 Uiso 1 1 calc R . . . .
C12 C 0.0011(4) 0.7428(2) 0.61875(9) 0.0615(7) Uani 1 1 d . . . . .
H12A H -0.073991 0.712944 0.637970 0.074 Uiso 1 1 calc R . . . .
H12B H -0.066651 0.803445 0.611626 0.074 Uiso 1 1 calc R . . . .
C13 C 0.0072(4) 0.6706(2) 0.58741(9) 0.0617(7) Uani 1 1 d . . . . .
H13 H -0.125285 0.658955 0.577484 0.074 Uiso 1 1 calc R . . . .
C14 C 0.1042(5) 0.5735(2) 0.60024(9) 0.0602(7) Uani 1 1 d . . . . .
H14A H 0.087574 0.520408 0.583015 0.072 Uiso 1 1 calc R . . . .
H14B H 0.049367 0.552320 0.622815 0.072 Uiso 1 1 calc R . . . .
C15 C 0.3491(4) 0.6639(2) 0.56987(8) 0.0539(6) Uani 1 1 d . . . . .
C16 C 0.1508(5) 0.7051(2) 0.55978(8) 0.0574(7) Uani 1 1 d . . . . .
C17 C 0.1223(6) 0.7611(3) 0.53143(9) 0.0716(9) Uani 1 1 d . . . . .
H17A H -0.003880 0.785402 0.526307 0.086 Uiso 1 1 calc R . . . .
H17B H 0.228395 0.776252 0.516577 0.086 Uiso 1 1 calc R . . . .
C18 C 0.4805(7) 0.4208(3) 0.72174(11) 0.0815(10) Uani 1 1 d . . . . .
H18A H 0.463088 0.417374 0.747263 0.098 Uiso 1 1 calc R . . . .
H18B H 0.373808 0.391314 0.707982 0.098 Uiso 1 1 calc R . . . .
C20 C 0.1828(4) 0.5991(2) 0.68827(8) 0.0597(7) Uani 1 1 d . . . . .
H20A H 0.087628 0.652418 0.687412 0.090 Uiso 1 1 calc GR . . . .
H20B H 0.202560 0.579062 0.712462 0.090 Uiso 1 1 calc GR . . . .
H20C H 0.134365 0.543552 0.674752 0.090 Uiso 1 1 calc GR . . . .
O1A O 1.0437(6) 0.1975(3) 0.70829(10) 0.1234(13) Uani 1 1 d . . . . .
H1AA H 1.073915 0.142494 0.716154 0.185 Uiso 1 1 calc GR . . . .
O2A O 1.0190(4) 0.3312(2) 0.64964(8) 0.0896(8) Uani 1 1 d . . . . .
O3A O 0.2466(3) 0.17999(17) 0.53813(6) 0.0682(6) Uani 1 1 d . . . . .
C1A C 0.6999(6) 0.0519(3) 0.64893(8) 0.0731(9) Uani 1 1 d . . . . .
H1AB H 0.569456 0.077143 0.655123 0.088 Uiso 1 1 calc R . . . .
H1AC H 0.689542 -0.019965 0.646525 0.088 Uiso 1 1 calc R . . . .
C2A C 0.8444(7) 0.0758(3) 0.67912(10) 0.0888(12) Uani 1 1 d . . . . .
H2AA H 0.788546 0.051823 0.701261 0.107 Uiso 1 1 calc R . . . .
H2AB H 0.967787 0.040225 0.675065 0.107 Uiso 1 1 calc R . . . .
C3A C 0.8891(7) 0.1866(3) 0.68267(10) 0.0862(11) Uani 1 1 d . . . . .
H3A H 0.769904 0.220350 0.691531 0.103 Uiso 1 1 calc R . . . .
C4A C 0.9430(5) 0.2305(3) 0.64722(9) 0.0692(9) Uani 1 1 d . . . . .
C5A C 0.7858(4) 0.2116(2) 0.61906(8) 0.0537(6) Uani 1 1 d . . . . .
H5A H 0.659780 0.234059 0.629315 0.064 Uiso 1 1 calc R . . . .
C6A C 0.8113(5) 0.2696(2) 0.58477(8) 0.0590(7) Uani 1 1 d . . . . .
H6AA H 0.928997 0.246409 0.572424 0.071 Uiso 1 1 calc R . . . .
H6AB H 0.828565 0.339850 0.590055 0.071 Uiso 1 1 calc R . . . .
C7A C 0.6301(5) 0.2555(2) 0.56129(8) 0.0581(7) Uani 1 1 d . . . . .
H7AA H 0.647554 0.293526 0.539615 0.070 Uiso 1 1 calc R . . . .
H7AB H 0.513955 0.281376 0.573423 0.070 Uiso 1 1 calc R . . . .
C8A C 0.5950(4) 0.1464(2) 0.55190(7) 0.0477(6) Uani 1 1 d . . . . .
C9A C 0.5893(4) 0.08048(19) 0.58604(7) 0.0477(6) Uani 1 1 d . . . . .
H9A H 0.469732 0.101886 0.598761 0.057 Uiso 1 1 calc R . . . .
C10A C 0.7626(4) 0.0967(2) 0.61280(7) 0.0516(6) Uani 1 1 d . . . . .
C11A C 0.5494(5) -0.0303(2) 0.57592(9) 0.0623(8) Uani 1 1 d . . . . .
H11C H 0.594543 -0.072147 0.595298 0.075 Uiso 1 1 calc R . . . .
H11D H 0.406960 -0.039564 0.573771 0.075 Uiso 1 1 calc R . . . .
C12A C 0.6469(5) -0.0670(2) 0.54178(10) 0.0705(9) Uani 1 1 d . . . . .
H12C H 0.786463 -0.079961 0.546179 0.085 Uiso 1 1 calc R . . . .
H12D H 0.585308 -0.129201 0.534555 0.085 Uiso 1 1 calc R . . . .
C13A C 0.6272(5) 0.0086(2) 0.51207(9) 0.0644(8) Uani 1 1 d . . . . .
H13A H 0.678366 -0.017551 0.489582 0.077 Uiso 1 1 calc R . . . .
C14A C 0.7357(5) 0.1049(2) 0.52317(8) 0.0607(7) Uani 1 1 d . . . . .
H14C H 0.748770 0.150779 0.503411 0.073 Uiso 1 1 calc R . . . .
H14D H 0.866306 0.090606 0.532791 0.073 Uiso 1 1 calc R . . . .
C15A C 0.3951(4) 0.1307(2) 0.53334(8) 0.0533(7) Uani 1 1 d . . . . .
C16A C 0.4158(5) 0.0448(2) 0.50845(8) 0.0602(7) Uani 1 1 d . . . . .
C17A C 0.2689(6) 0.0092(3) 0.48874(9) 0.0741(9) Uani 1 1 d . . . . .
H17C H 0.143418 0.038040 0.489952 0.089 Uiso 1 1 calc R . . . .
H17D H 0.291243 -0.044640 0.473700 0.089 Uiso 1 1 calc R . . . .
C18A C 1.1493(6) 0.2517(3) 0.63787(13) 0.0896(12) Uani 1 1 d . . . . .
H18C H 1.252135 0.229341 0.654060 0.107 Uiso 1 1 calc R . . . .
H18D H 1.185464 0.249841 0.612969 0.107 Uiso 1 1 calc R . . . .
C20A C 0.9593(5) 0.0498(2) 0.60066(10) 0.0629(8) Uani 1 1 d . . . . .
H20D H 0.938718 -0.019544 0.595435 0.094 Uiso 1 1 calc GR . . . .
H20E H 1.056295 0.056111 0.619194 0.094 Uiso 1 1 calc GR . . . .
H20F H 1.005837 0.083379 0.579766 0.094 Uiso 1 1 calc GR . . . .
O1S O 1.0348(8) 0.3761(4) 0.74314(13) 0.1438(16) Uani 1 1 d . . . . .
H1S H 1.043577 0.325278 0.731128 0.216 Uiso 1 1 calc R . . . .
C1S C 1.0110(13) 0.3538(5) 0.7738(2) 0.167(4) Uani 1 1 d . . . . .
H1SA H 0.928192 0.295637 0.775229 0.251 Uiso 1 1 calc GR . . . .
H1SB H 0.948468 0.408042 0.786080 0.251 Uiso 1 1 calc GR . . . .
H1SC H 1.137437 0.339872 0.784476 0.251 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0410 0.0250 '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
C3 O1 H1 109.5 . . ?
C4 O2 C18 60.4(2) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C2 C1 C10 112.9(2) . . ?
C10 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.5(3) . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
O1 C3 C2 110.9(3) . . ?
O1 C3 H3 108.1 . . ?
O1 C3 C4 111.0(3) . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 110.5(3) . . ?
C4 C3 H3 108.1 . . ?
O2 C4 C3 114.9(3) . . ?
O2 C4 C5 115.2(2) . . ?
O2 C4 C18 59.9(2) . . ?
C3 C4 C5 112.5(2) . . ?
C18 C4 C3 120.7(3) . . ?
C18 C4 C5 122.4(3) . . ?
C4 C5 H5 105.8 . . ?
C4 C5 C6 115.2(2) . . ?
C4 C5 C10 110.7(2) . . ?
C6 C5 H5 105.8 . . ?
C6 C5 C10 112.7(2) . . ?
C10 C5 H5 105.8 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 C5 109.8(2) . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 113.0(2) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 C9 111.2(2) . . ?
C7 C8 C14 115.6(2) . . ?
C7 C8 C15 112.4(2) . . ?
C14 C8 C9 112.4(2) . . ?
C15 C8 C9 104.7(2) . . ?
C15 C8 C14 99.6(2) . . ?
C8 C9 H9 104.8 . . ?
C10 C9 C8 115.3(2) . . ?
C10 C9 H9 104.8 . . ?
C11 C9 C8 110.8(2) . . ?
C11 C9 H9 104.8 . . ?
C11 C9 C10 115.0(2) . . ?
C1 C10 C5 106.3(2) . . ?
C1 C10 C9 108.0(2) . . ?
C5 C10 C9 108.0(2) . . ?
C20 C10 C1 109.8(2) . . ?
C20 C10 C5 111.2(2) . . ?
C20 C10 C9 113.2(2) . . ?
C9 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C9 116.2(2) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 111.9(2) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13 111.8 . . ?
C12 C13 C14 107.8(3) . . ?
C14 C13 H13 111.8 . . ?
C16 C13 C12 111.1(3) . . ?
C16 C13 H13 111.8 . . ?
C16 C13 C14 101.9(2) . . ?
C8 C14 H14A 111.3 . . ?
C8 C14 H14B 111.3 . . ?
C13 C14 C8 102.5(2) . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
O3 C15 C8 125.9(3) . . ?
O3 C15 C16 125.9(3) . . ?
C16 C15 C8 108.2(2) . . ?
C13 C16 C15 106.6(2) . . ?
C17 C16 C13 130.3(3) . . ?
C17 C16 C15 123.1(3) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
O2 C18 C4 59.7(2) . . ?
O2 C18 H18A 117.8 . . ?
O2 C18 H18B 117.8 . . ?
C4 C18 H18A 117.8 . . ?
C4 C18 H18B 117.8 . . ?
H18A C18 H18B 114.9 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3A O1A H1AA 109.5 . . ?
C4A O2A C18A 60.6(2) . . ?
H1AB C1A H1AC 107.7 . . ?
C2A C1A H1AB 108.9 . . ?
C2A C1A H1AC 108.9 . . ?
C2A C1A C10A 113.6(3) . . ?
C10A C1A H1AB 108.9 . . ?
C10A C1A H1AC 108.9 . . ?
C1A C2A H2AA 108.9 . . ?
C1A C2A H2AB 108.9 . . ?
H2AA C2A H2AB 107.7 . . ?
C3A C2A C1A 113.3(3) . . ?
C3A C2A H2AA 108.9 . . ?
C3A C2A H2AB 108.9 . . ?
O1A C3A C2A 107.7(3) . . ?
O1A C3A H3A 108.6 . . ?
O1A C3A C4A 112.6(4) . . ?
C2A C3A H3A 108.6 . . ?
C4A C3A C2A 110.6(3) . . ?
C4A C3A H3A 108.6 . . ?
O2A C4A C3A 113.2(3) . . ?
O2A C4A C5A 116.5(3) . . ?
O2A C4A C18A 59.8(2) . . ?
C3A C4A C5A 112.7(3) . . ?
C18A C4A C3A 121.3(3) . . ?
C18A C4A C5A 121.8(3) . . ?
C4A C5A H5A 106.0 . . ?
C4A C5A C10A 109.8(2) . . ?
C6A C5A C4A 115.5(3) . . ?
C6A C5A H5A 106.0 . . ?
C6A C5A C10A 112.8(2) . . ?
C10A C5A H5A 106.0 . . ?
C5A C6A H6AA 109.7 . . ?
C5A C6A H6AB 109.7 . . ?
C5A C6A C7A 110.0(2) . . ?
H6AA C6A H6AB 108.2 . . ?
C7A C6A H6AA 109.7 . . ?
C7A C6A H6AB 109.7 . . ?
C6A C7A H7AA 109.1 . . ?
C6A C7A H7AB 109.1 . . ?
C6A C7A C8A 112.3(2) . . ?
H7AA C7A H7AB 107.9 . . ?
C8A C7A H7AA 109.1 . . ?
C8A C7A H7AB 109.1 . . ?
C7A C8A C9A 110.9(2) . . ?
C7A C8A C14A 114.5(2) . . ?
C7A C8A C15A 112.0(2) . . ?
C14A C8A C9A 112.9(2) . . ?
C15A C8A C9A 106.1(2) . . ?
C15A C8A C14A 99.7(2) . . ?
C8A C9A H9A 104.9 . . ?
C10A C9A C8A 115.8(2) . . ?
C10A C9A H9A 104.9 . . ?
C11A C9A C8A 110.1(2) . . ?
C11A C9A H9A 104.9 . . ?
C11A C9A C10A 114.9(2) . . ?
C1A C10A C5A 106.1(2) . . ?
C1A C10A C9A 108.1(2) . . ?
C9A C10A C5A 108.0(2) . . ?
C20A C10A C1A 109.8(3) . . ?
C20A C10A C5A 111.2(2) . . ?
C20A C10A C9A 113.3(2) . . ?
C9A C11A H11C 108.3 . . ?
C9A C11A H11D 108.3 . . ?
H11C C11A H11D 107.4 . . ?
C12A C11A C9A 116.1(3) . . ?
C12A C11A H11C 108.3 . . ?
C12A C11A H11D 108.3 . . ?
C11A C12A H12C 109.3 . . ?
C11A C12A H12D 109.3 . . ?
H12C C12A H12D 107.9 . . ?
C13A C12A C11A 111.7(2) . . ?
C13A C12A H12C 109.3 . . ?
C13A C12A H12D 109.3 . . ?
C12A C13A H13A 111.6 . . ?
C12A C13A C14A 108.6(3) . . ?
C14A C13A H13A 111.6 . . ?
C16A C13A C12A 111.3(3) . . ?
C16A C13A H13A 111.6 . . ?
C16A C13A C14A 101.7(2) . . ?
C8A C14A H14C 111.4 . . ?
C8A C14A H14D 111.4 . . ?
C13A C14A C8A 101.6(2) . . ?
C13A C14A H14C 111.4 . . ?
C13A C14A H14D 111.4 . . ?
H14C C14A H14D 109.3 . . ?
O3A C15A C8A 125.5(3) . . ?
O3A C15A C16A 126.3(3) . . ?
C16A C15A C8A 108.2(2) . . ?
C15A C16A C13A 106.2(3) . . ?
C17A C16A C13A 129.7(3) . . ?
C17A C16A C15A 124.1(3) . . ?
C16A C17A H17C 120.0 . . ?
C16A C17A H17D 120.0 . . ?
H17C C17A H17D 120.0 . . ?
O2A C18A C4A 59.6(2) . . ?
O2A C18A H18C 117.8 . . ?
O2A C18A H18D 117.8 . . ?
C4A C18A H18C 117.8 . . ?
C4A C18A H18D 117.8 . . ?
H18C C18A H18D 114.9 . . ?
C10A C20A H20D 109.5 . . ?
C10A C20A H20E 109.5 . . ?
C10A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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
O1 H1 0.8200 . ?
O1 C3 1.432(4) . ?
O2 C4 1.445(4) . ?
O2 C18 1.448(5) . ?
O3 C15 1.216(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(4) . ?
C1 C10 1.551(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.500(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.499(5) . ?
C4 C5 1.521(4) . ?
C4 C18 1.456(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.523(4) . ?
C5 C10 1.552(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.520(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.517(4) . ?
C8 C9 1.577(4) . ?
C8 C14 1.541(4) . ?
C8 C15 1.529(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.558(4) . ?
C9 C11 1.555(4) . ?
C10 C20 1.535(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.531(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.528(5) . ?
C13 H13 0.9800 . ?
C13 C14 1.535(5) . ?
C13 C16 1.494(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.495(4) . ?
C16 C17 1.320(4) . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1A H1AA 0.8200 . ?
O1A C3A 1.427(5) . ?
O2A C4A 1.447(4) . ?
O2A C18A 1.450(5) . ?
O3A C15A 1.212(3) . ?
C1A H1AB 0.9700 . ?
C1A H1AC 0.9700 . ?
C1A C2A 1.531(5) . ?
C1A C10A 1.547(4) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.522(6) . ?
C3A H3A 0.9800 . ?
C3A C4A 1.505(6) . ?
C4A C5A 1.520(4) . ?
C4A C18A 1.461(5) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.518(4) . ?
C5A C10A 1.566(4) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C7A 1.519(4) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.523(4) . ?
C8A C9A 1.562(4) . ?
C8A C14A 1.543(4) . ?
C8A C15A 1.532(4) . ?
C9A H9A 0.9800 . ?
C9A C10A 1.558(4) . ?
C9A C11A 1.557(4) . ?
C10A C20A 1.536(4) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.526(5) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A C13A 1.517(5) . ?
C13A H13A 0.9800 . ?
C13A C14A 1.541(4) . ?
C13A C16A 1.510(5) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C15A C16A 1.492(4) . ?
C16A C17A 1.326(5) . ?
C17A H17C 0.9300 . ?
C17A H17D 0.9300 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
O1S H1S 0.8200 . ?
O1S C1S 1.203(7) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1AA O1 0.82 2.09 2.819(5) 148.6 3_746 yes
O1S H1S O1A 0.82 1.92 2.732(6) 171.9 . yes
