#------------------------------------------------------------------------------
#$Date: 2020-08-04 05:16:18 +0300 (Tue, 04 Aug 2020) $
#$Revision: 254773 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558524.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_1558524
loop_
_publ_author_name
'Pu, De-Bing'
'Zhang, Xing-Jie'
'Bi, De-Wen'
'Gao, Jun-Bo'
'Yang, Yan'
'Li, Xiao-Li'
'Lin, Jing'
'Li, Xiao-Nian'
'Zhang, Rui-Han'
'Xiao, Wei-Lie'
_publ_section_title
;
 Callicarpins, Two Classes of Rearranged ent-Clerodane Diterpenoids
 from Callicarpa Plants Blocking NLRP3 Inflammasome-Induced
 Pyroptosis.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2191
_journal_page_last               2199
_journal_paper_doi               10.1021/acs.jnatprod.0c00288
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H32 O7, H2 O'
_chemical_formula_sum            'C21 H34 O8'
_chemical_formula_weight         414.48
_chemical_name_common            xpc67
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.440(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4232(11)
_cell_length_b                   30.675(4)
_cell_length_c                   8.5481(11)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      72.8445
_cell_measurement_theta_min      2.8811
_cell_volume                     2164.8(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21593
_diffrn_reflns_theta_full        72.92
_diffrn_reflns_theta_max         72.92
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.561
_refine_ls_abs_structure_details
; 
  
Flack x determined using 2504 quotients [(I+)-(I-)]/[(I+)+(I-)] 
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.752
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         8175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.752
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.1454
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3939
_refine_ls_wR_factor_ref         0.4141
_reflns_number_gt                6808
_reflns_number_total             8175
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00288_si_006.cif
_cod_data_source_block           xpc67
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1558521--1558525.cif.
;
_cod_database_code               1558524
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9040(11) 0.4541(3) 1.0201(10) 0.0580(18) Uani d . . . 1 . .
O O2 0.2792(11) 0.5903(3) 0.3127(10) 0.0572(18) Uani d . . . 1 . .
O O3 0.5879(9) 0.5638(2) 0.5931(9) 0.0474(15) Uani d . . . 1 . .
H H59 0.575944 0.537914 0.561287 0.071 Uiso calc U . R 1 . .
O O4 0.5489(10) 0.6180(3) 0.0893(9) 0.0527(16) Uani d . . . 1 . .
H H60 0.61035 0.603595 0.160227 0.079 Uiso calc U . R 1 . .
O O5 0.1762(10) 0.6221(3) 0.0790(9) 0.0569(18) Uani d . . . 1 . .
O O6 1.0515(10) 0.5059(3) 0.9316(11) 0.0581(19) Uani d . . . 1 . .
O O7 1.1058(10) 0.5402(3) 0.7058(11) 0.0597(19) Uani d . . . 1 . .
H H61 1.0455 0.546882 0.618578 0.09 Uiso calc U . R 1 . .
O O8 0.0004(10) 0.4103(3) -0.4009(10) 0.0565(18) Uani d . . . 1 . .
O O9 0.7067(10) 0.5451(2) 0.2418(10) 0.0558(17) Uani d . . . 1 . .
O O10 0.6058(10) 0.4934(2) 0.3819(9) 0.0522(17) Uani d . . . 1 . .
O O11 -0.2356(10) 0.3785(3) -0.5082(10) 0.0570(18) Uani d . . . 1 . .
O O12 -0.2395(10) 0.3810(3) -0.1484(9) 0.0553(17) Uani d . . . 1 . .
H H62 -0.183135 0.391775 -0.065382 0.083 Uiso calc U . R 1 . .
O O13 0.2716(9) 0.4361(3) -0.0770(8) 0.0495(15) Uani d . . . 1 . .
H H63 0.243947 0.462443 -0.087729 0.074 Uiso calc U . R 1 . .
O O14 0.3672(10) 0.4592(3) 0.4259(9) 0.0577(18) Uani d . . . 1 . .
H H64 0.400116 0.456028 0.524656 0.087 Uiso calc U . R 1 . .
C C1 0.9073(13) 0.4857(3) 0.9320(14) 0.050(2) Uani d . . . 1 . .
C C2 0.7766(14) 0.5078(3) 0.8287(13) 0.049(2) Uani d . . . 1 . .
H H29 0.665341 0.49996 0.809599 0.059 Uiso calc U . R 1 . .
C C3 0.8425(13) 0.5420(3) 0.7636(13) 0.047(2) Uani d . . . 1 . .
C C4 0.7571(13) 0.5736(4) 0.6376(12) 0.048(2) Uani d . . . 1 . .
H H27 0.806188 0.570676 0.540711 0.058 Uiso calc U . R 1 . .
C C5 0.7782(13) 0.6220(4) 0.6968(12) 0.049(2) Uani d . . . 1 . .
H H2 0.683779 0.629693 0.744155 0.059 Uiso calc U . R 1 . .
H H3 0.875474 0.623495 0.78331 0.059 Uiso calc U . R 1 . .
C C6 0.7949(13) 0.6566(3) 0.5738(13) 0.048(2) Uani d . . . 1 . .
C C7 0.6605(13) 0.6515(3) 0.4202(12) 0.047(2) Uani d . . . 1 . .
H H26 0.667318 0.62024 0.388655 0.056 Uiso calc U . R 1 . .
C C8 0.4826(13) 0.6581(3) 0.4317(13) 0.049(2) Uani d . . . 1 . .
H H7 0.444543 0.633985 0.491945 0.058 Uiso calc U . R 1 . .
H H25 0.468093 0.686017 0.485184 0.058 Uiso calc U . R 1 . .
C C9 0.3905(12) 0.6585(3) 0.2580(14) 0.050(2) Uani d . . . 1 . .
H H8 0.329096 0.686529 0.241227 0.06 Uiso calc U . R 1 . .
C C10 0.2705(13) 0.6220(4) 0.1990(13) 0.051(2) Uani d . . . 1 . .
C C11 0.1619(16) 0.5547(4) 0.2726(16) 0.062(3) Uani d . . . 1 . .
H H24 0.066961 0.565219 0.196589 0.093 Uiso calc U . R 1 . .
H H23 0.128448 0.544489 0.369817 0.093 Uiso calc U . R 1 . .
H H1 0.211976 0.530601 0.224719 0.093 Uiso calc U . R 1 . .
C C12 0.7880(14) 0.7005(4) 0.6594(13) 0.053(2) Uani d . . . 1 . .
H H4 0.67544 0.707176 0.665145 0.079 Uiso calc U . R 1 . .
H H6 0.830572 0.723628 0.59999 0.079 Uiso calc U . R 1 . .
H H5 0.853471 0.698791 0.767611 0.079 Uiso calc U . R 1 . .
C C13 0.5221(14) 0.6600(4) 0.1496(13) 0.055(2) Uani d . . . 1 . .
C C14 0.6782(14) 0.6772(3) 0.2727(13) 0.051(2) Uani d . . . 1 . .
C C15 0.8430(14) 0.6689(4) 0.2282(14) 0.053(2) Uani d . . . 1 . .
H H16 0.848474 0.638379 0.191642 0.064 Uiso calc U . R 1 . .
H H9 0.856576 0.688431 0.139688 0.064 Uiso calc U . R 1 . .
O O16 1.4041(10) 0.5673(3) 0.8271(10) 0.0607(19) Uani d . . . 1 . .
O O15 0.4863(10) 0.4305(3) 0.7167(9) 0.0579(18) Uani d . . . 1 . .
C C16 0.9778(15) 0.6770(4) 0.3714(14) 0.054(2) Uani d . . . 1 . .
H H15 0.979963 0.708501 0.396851 0.065 Uiso calc U . R 1 . .
H H14 1.082303 0.669635 0.341615 0.065 Uiso calc U . R 1 . .
C C17 0.9645(13) 0.6511(4) 0.5240(13) 0.051(2) Uani d . . . 1 . .
H H10 0.971322 0.619687 0.495198 0.062 Uiso calc U . R 1 . .
C C18 1.1103(15) 0.6596(4) 0.6531(16) 0.059(3) Uani d . . . 1 . .
H H13 1.205366 0.645543 0.625017 0.088 Uiso calc U . R 1 . .
H H11 1.091702 0.647623 0.75427 0.088 Uiso calc U . R 1 . .
H H12 1.128946 0.691051 0.664239 0.088 Uiso calc U . R 1 . .
C C19 0.6572(15) 0.7271(4) 0.2862(13) 0.055(2) Uani d . . . 1 . .
H H19 0.556661 0.733283 0.323246 0.083 Uiso calc U . R 1 . .
H H17 0.652526 0.740575 0.181382 0.083 Uiso calc U . R 1 . .
H H18 0.749293 0.739087 0.362425 0.083 Uiso calc U . R 1 . .
C C20 0.4702(16) 0.6885(4) 0.0013(14) 0.059(3) Uani d . . . 1 . .
H H22 0.559278 0.690498 -0.056673 0.088 Uiso calc U . R 1 . .
H H21 0.442557 0.717718 0.033651 0.088 Uiso calc U . R 1 . .
H H20 0.375416 0.675458 -0.068051 0.088 Uiso calc U . R 1 . .
C C21 1.0216(15) 0.5440(3) 0.8256(14) 0.053(2) Uani d . . . 1 . .
H H28 1.051661 0.57146 0.887121 0.064 Uiso calc U . R 1 . .
C C22 -0.0350(19) 0.4456(5) -0.5130(18) 0.072(3) Uani d . . . 1 . .
H H51 -0.066674 0.433855 -0.621265 0.107 Uiso calc U . R 1 . .
H H52 0.061458 0.463924 -0.506269 0.107 Uiso calc U . R 1 . .
H H30 -0.123864 0.463135 -0.487671 0.107 Uiso calc U . R 1 . .
C C23 -0.1112(14) 0.3784(3) -0.4129(12) 0.049(2) Uani d . . . 1 . .
C C24 -0.0553(14) 0.3407(3) -0.2958(12) 0.049(2) Uani d . . . 1 . .
H H48 -0.065319 0.312864 -0.357997 0.059 Uiso calc U . R 1 . .
C C25 0.1194(13) 0.3437(3) -0.1966(12) 0.048(2) Uani d . . . 1 . .
H H50 0.18206 0.317118 -0.210071 0.058 Uiso calc U . R 1 . .
H H49 0.176527 0.369421 -0.228381 0.058 Uiso calc U . R 1 . .
C C26 0.0953(13) 0.3481(3) -0.0234(12) 0.046(2) Uani d . . . 1 . .
H H53 0.06123 0.379055 -0.015102 0.055 Uiso calc U . R 1 . .
C C27 0.2434(13) 0.3427(3) 0.1146(13) 0.048(2) Uani d . . . 1 . .
C C28 0.3730(13) 0.3783(4) 0.1053(12) 0.050(2) Uani d . . . 1 . .
H H57 0.458333 0.376158 0.20302 0.06 Uiso calc U . R 1 . .
H H33 0.424144 0.371373 0.013516 0.06 Uiso calc U . R 1 . .
C C29 0.3134(13) 0.4257(3) 0.0881(12) 0.048(2) Uani d . . . 1 . .
H H32 0.214229 0.428274 0.13519 0.058 Uiso calc U . R 1 . .
C C30 0.4381(14) 0.4574(4) 0.1712(13) 0.050(2) Uani d . . . 1 . .
C C31 0.5078(14) 0.4900(4) 0.1104(13) 0.051(2) Uani d . . . 1 . .
H H58 0.492084 0.497606 0.000632 0.061 Uiso calc U . R 1 . .
C C32 0.6156(15) 0.5130(4) 0.2444(14) 0.055(2) Uani d . . . 1 . .
C C33 0.4960(13) 0.4560(3) 0.3499(12) 0.048(2) Uani d . . . 1 . .
H H31 0.556907 0.428317 0.381433 0.057 Uiso calc U . R 1 . .
C C34 -0.0601(13) 0.3215(4) -0.0235(13) 0.051(2) Uani d . . . 1 . .
C C35 -0.0378(15) 0.2724(4) -0.0421(14) 0.055(2) Uani d . . . 1 . .
H H35 0.003731 0.266817 -0.139434 0.082 Uiso calc U . R 1 . .
H H36 -0.142273 0.257706 -0.049243 0.082 Uiso calc U . R 1 . .
H H34 0.039291 0.261344 0.050502 0.082 Uiso calc U . R 1 . .
C C36 -0.1155(17) 0.3298(4) 0.1362(15) 0.058(3) Uani d . . . 1 . .
H H37 -0.151677 0.360414 0.141165 0.07 Uiso calc U . R 1 . .
H H44 -0.207342 0.310421 0.144677 0.07 Uiso calc U . R 1 . .
C C37 0.0282(16) 0.3207(4) 0.2740(13) 0.056(3) Uani d . . . 1 . .
H H39 -0.0069 0.325767 0.376344 0.068 Uiso calc U . R 1 . .
H H38 0.05847 0.289575 0.270399 0.068 Uiso calc U . R 1 . .
C C38 0.1777(14) 0.3486(4) 0.2705(13) 0.052(2) Uani d . . . 1 . .
H H40 0.143201 0.379707 0.273714 0.062 Uiso calc U . R 1 . .
C C39 0.3075(16) 0.3405(4) 0.4238(14) 0.056(2) Uani d . . . 1 . .
H H42 0.26533 0.349867 0.517309 0.084 Uiso calc U . R 1 . .
H H43 0.405454 0.357145 0.417999 0.084 Uiso calc U . R 1 . .
H H41 0.333735 0.309354 0.432961 0.084 Uiso calc U . R 1 . .
C C40 -0.1766(15) 0.3388(3) -0.1769(13) 0.050(2) Uani d . . . 1 . .
C C41 -0.3246(16) 0.3120(4) -0.2379(17) 0.064(3) Uani d . . . 1 . .
H H46 -0.391932 0.310702 -0.156735 0.096 Uiso calc U . R 1 . .
H H45 -0.292246 0.282372 -0.261527 0.096 Uiso calc U . R 1 . .
H H47 -0.386572 0.32525 -0.335401 0.096 Uiso calc U . R 1 . .
C C42 0.3354(14) 0.2996(4) 0.1124(13) 0.053(2) Uani d . . . 1 . .
H H56 0.267445 0.275454 0.1353 0.08 Uiso calc U . R 1 . .
H H54 0.435411 0.30051 0.193592 0.08 Uiso calc U . R 1 . .
H H55 0.362047 0.29542 0.00693 0.08 Uiso calc U . R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O2 C11 . . 115.2(9) ?
C4 O3 H59 . . 109.5 ?
C13 O4 H60 . . 109.5 ?
C1 O6 C21 . . 108.6(9) ?
C21 O7 H61 . . 109.5 ?
C23 O8 C22 . . 116.6(10) ?
C32 O10 C33 . . 109.5(8) ?
C40 O12 H62 . . 109.5 ?
C29 O13 H63 . . 109.5 ?
C33 O14 H64 . . 109.5 ?
O1 C1 O6 . . 119.2(10) ?
O1 C1 C2 . . 129.8(10) ?
O6 C1 C2 . . 111.0(9) ?
C3 C2 C1 . . 106.9(10) ?
C3 C2 H29 . . 126.5 ?
C1 C2 H29 . . 126.5 ?
C2 C3 C21 . . 110.5(10) ?
C2 C3 C4 . . 127.6(10) ?
C21 C3 C4 . . 121.8(9) ?
O3 C4 C3 . . 111.1(8) ?
O3 C4 C5 . . 109.1(8) ?
C3 C4 C5 . . 111.6(8) ?
O3 C4 H27 . . 108.3 ?
C3 C4 H27 . . 108.3 ?
C5 C4 H27 . . 108.3 ?
C6 C5 C4 . . 117.3(8) ?
C6 C5 H2 . . 108.0 ?
C4 C5 H2 . . 108.0 ?
C6 C5 H3 . . 108.0 ?
C4 C5 H3 . . 108.0 ?
H2 C5 H3 . . 107.2 ?
C5 C6 C12 . . 105.4(9) ?
C5 C6 C7 . . 111.1(8) ?
C12 C6 C7 . . 113.5(9) ?
C5 C6 C17 . . 108.9(9) ?
C12 C6 C17 . . 110.1(9) ?
C7 C6 C17 . . 107.9(8) ?
C14 C7 C8 . . 104.0(8) ?
C14 C7 C6 . . 118.1(9) ?
C8 C7 C6 . . 119.1(8) ?
C14 C7 H26 . . 104.7 ?
C8 C7 H26 . . 104.7 ?
C6 C7 H26 . . 104.7 ?
C9 C8 C7 . . 104.6(8) ?
C9 C8 H7 . . 110.8 ?
C7 C8 H7 . . 110.8 ?
C9 C8 H25 . . 110.8 ?
C7 C8 H25 . . 110.8 ?
H7 C8 H25 . . 108.9 ?
C10 C9 C8 . . 119.3(9) ?
C10 C9 C13 . . 108.9(9) ?
C8 C9 C13 . . 106.8(8) ?
C10 C9 H8 . . 107.1 ?
C8 C9 H8 . . 107.1 ?
C13 C9 H8 . . 107.1 ?
O5 C10 O2 . . 123.9(10) ?
O5 C10 C9 . . 125.5(10) ?
O2 C10 C9 . . 110.4(9) ?
O2 C11 H24 . . 109.5 ?
O2 C11 H23 . . 109.5 ?
H24 C11 H23 . . 109.5 ?
O2 C11 H1 . . 109.5 ?
H24 C11 H1 . . 109.5 ?
H23 C11 H1 . . 109.5 ?
C6 C12 H4 . . 109.5 ?
C6 C12 H6 . . 109.5 ?
H4 C12 H6 . . 109.5 ?
C6 C12 H5 . . 109.5 ?
H4 C12 H5 . . 109.5 ?
H6 C12 H5 . . 109.5 ?
O4 C13 C20 . . 104.9(9) ?
O4 C13 C9 . . 111.4(9) ?
C20 C13 C9 . . 112.6(10) ?
O4 C13 C14 . . 111.6(9) ?
C20 C13 C14 . . 114.8(9) ?
C9 C13 C14 . . 101.8(8) ?
C7 C14 C15 . . 111.3(9) ?
C7 C14 C19 . . 114.9(9) ?
C15 C14 C19 . . 107.8(9) ?
C7 C14 C13 . . 99.9(8) ?
C15 C14 C13 . . 116.7(9) ?
C19 C14 C13 . . 106.5(9) ?
C16 C15 C14 . . 110.0(9) ?
C16 C15 H16 . . 109.7 ?
C14 C15 H16 . . 109.7 ?
C16 C15 H9 . . 109.7 ?
C14 C15 H9 . . 109.7 ?
H16 C15 H9 . . 108.2 ?
C15 C16 C17 . . 115.4(9) ?
C15 C16 H15 . . 108.4 ?
C17 C16 H15 . . 108.4 ?
C15 C16 H14 . . 108.4 ?
C17 C16 H14 . . 108.4 ?
H15 C16 H14 . . 107.5 ?
C18 C17 C16 . . 110.2(9) ?
C18 C17 C6 . . 115.8(9) ?
C16 C17 C6 . . 113.1(9) ?
C18 C17 H10 . . 105.6 ?
C16 C17 H10 . . 105.6 ?
C6 C17 H10 . . 105.6 ?
C17 C18 H13 . . 109.5 ?
C17 C18 H11 . . 109.5 ?
H13 C18 H11 . . 109.5 ?
C17 C18 H12 . . 109.5 ?
H13 C18 H12 . . 109.5 ?
H11 C18 H12 . . 109.5 ?
C14 C19 H19 . . 109.5 ?
C14 C19 H17 . . 109.5 ?
H19 C19 H17 . . 109.5 ?
C14 C19 H18 . . 109.5 ?
H19 C19 H18 . . 109.5 ?
H17 C19 H18 . . 109.5 ?
C13 C20 H22 . . 109.5 ?
C13 C20 H21 . . 109.5 ?
H22 C20 H21 . . 109.5 ?
C13 C20 H20 . . 109.5 ?
H22 C20 H20 . . 109.5 ?
H21 C20 H20 . . 109.5 ?
O7 C21 O6 . . 110.2(9) ?
O7 C21 C3 . . 111.7(10) ?
O6 C21 C3 . . 103.0(8) ?
O7 C21 H28 . . 110.6 ?
O6 C21 H28 . . 110.6 ?
C3 C21 H28 . . 110.6 ?
O8 C22 H51 . . 109.5 ?
O8 C22 H52 . . 109.5 ?
H51 C22 H52 . . 109.5 ?
O8 C22 H30 . . 109.5 ?
H51 C22 H30 . . 109.5 ?
H52 C22 H30 . . 109.5 ?
O11 C23 O8 . . 123.8(10) ?
O11 C23 C24 . . 124.0(10) ?
O8 C23 C24 . . 112.2(9) ?
C23 C24 C25 . . 116.5(9) ?
C23 C24 C40 . . 107.0(9) ?
C25 C24 C40 . . 108.4(8) ?
C23 C24 H48 . . 108.2 ?
C25 C24 H48 . . 108.2 ?
C40 C24 H48 . . 108.2 ?
C26 C25 C24 . . 103.9(8) ?
C26 C25 H50 . . 111.0 ?
C24 C25 H50 . . 111.0 ?
C26 C25 H49 . . 111.0 ?
C24 C25 H49 . . 111.0 ?
H50 C25 H49 . . 109.0 ?
C25 C26 C34 . . 103.2(8) ?
C25 C26 C27 . . 119.0(9) ?
C34 C26 C27 . . 120.1(8) ?
C25 C26 H53 . . 104.2 ?
C34 C26 H53 . . 104.2 ?
C27 C26 H53 . . 104.2 ?
C42 C27 C26 . . 114.5(8) ?
C42 C27 C38 . . 112.2(9) ?
C26 C27 C38 . . 105.8(9) ?
C42 C27 C28 . . 104.0(9) ?
C26 C27 C28 . . 110.8(8) ?
C38 C27 C28 . . 109.6(8) ?
C29 C28 C27 . . 116.7(8) ?
C29 C28 H57 . . 108.1 ?
C27 C28 H57 . . 108.1 ?
C29 C28 H33 . . 108.1 ?
C27 C28 H33 . . 108.1 ?
H57 C28 H33 . . 107.3 ?
O13 C29 C30 . . 109.6(8) ?
O13 C29 C28 . . 108.7(8) ?
C30 C29 C28 . . 112.5(9) ?
O13 C29 H32 . . 108.6 ?
C30 C29 H32 . . 108.6 ?
C28 C29 H32 . . 108.6 ?
C31 C30 C29 . . 129.0(10) ?
C31 C30 C33 . . 109.9(10) ?
C29 C30 C33 . . 121.0(9) ?
C30 C31 C32 . . 107.9(10) ?
C30 C31 H58 . . 126.1 ?
C32 C31 H58 . . 126.1 ?
O9 C32 O10 . . 120.9(10) ?
O9 C32 C31 . . 129.8(11) ?
O10 C32 C31 . . 109.2(9) ?
O14 C33 O10 . . 112.6(9) ?
O14 C33 C30 . . 110.5(9) ?
O10 C33 C30 . . 103.4(8) ?
O14 C33 H31 . . 110.1 ?
O10 C33 H31 . . 110.1 ?
C30 C33 H31 . . 110.1 ?
C35 C34 C26 . . 113.4(9) ?
C35 C34 C36 . . 108.5(9) ?
C26 C34 C36 . . 108.5(9) ?
C35 C34 C40 . . 108.3(9) ?
C26 C34 C40 . . 102.3(8) ?
C36 C34 C40 . . 115.8(10) ?
C34 C35 H35 . . 109.5 ?
C34 C35 H36 . . 109.5 ?
H35 C35 H36 . . 109.5 ?
C34 C35 H34 . . 109.5 ?
H35 C35 H34 . . 109.5 ?
H36 C35 H34 . . 109.5 ?
C37 C36 C34 . . 108.4(10) ?
C37 C36 H37 . . 110.0 ?
C34 C36 H37 . . 110.0 ?
C37 C36 H44 . . 110.0 ?
C34 C36 H44 . . 110.0 ?
H37 C36 H44 . . 108.4 ?
C38 C37 C36 . . 114.2(9) ?
C38 C37 H39 . . 108.7 ?
C36 C37 H39 . . 108.7 ?
C38 C37 H38 . . 108.7 ?
C36 C37 H38 . . 108.7 ?
H39 C37 H38 . . 107.6 ?
C37 C38 C27 . . 112.8(9) ?
C37 C38 C39 . . 109.9(9) ?
C27 C38 C39 . . 113.3(9) ?
C37 C38 H40 . . 106.8 ?
C27 C38 H40 . . 106.8 ?
C39 C38 H40 . . 106.8 ?
C38 C39 H42 . . 109.5 ?
C38 C39 H43 . . 109.5 ?
H42 C39 H43 . . 109.5 ?
C38 C39 H41 . . 109.5 ?
H42 C39 H41 . . 109.5 ?
H43 C39 H41 . . 109.5 ?
O12 C40 C41 . . 104.1(10) ?
O12 C40 C34 . . 110.6(9) ?
C41 C40 C34 . . 116.5(9) ?
O12 C40 C24 . . 112.5(8) ?
C41 C40 C24 . . 113.4(10) ?
C34 C40 C24 . . 100.0(9) ?
C40 C41 H46 . . 109.5 ?
C40 C41 H45 . . 109.5 ?
H46 C41 H45 . . 109.5 ?
C40 C41 H47 . . 109.5 ?
H46 C41 H47 . . 109.5 ?
H45 C41 H47 . . 109.5 ?
C27 C42 H56 . . 109.5 ?
C27 C42 H54 . . 109.5 ?
H56 C42 H54 . . 109.5 ?
C27 C42 H55 . . 109.5 ?
H56 C42 H55 . . 109.5 ?
H54 C42 H55 . . 109.5 ?
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
O1 C1 . 1.231(14) ?
O2 C10 . 1.368(13) ?
O2 C11 . 1.466(14) ?
O3 C4 . 1.432(13) ?
O3 H59 . 0.84 ?
O4 C13 . 1.424(15) ?
O4 H60 . 0.84 ?
O5 C10 . 1.166(14) ?
O6 C1 . 1.363(13) ?
O6 C21 . 1.469(13) ?
O7 C21 . 1.361(15) ?
O7 H61 . 0.84 ?
O8 C23 . 1.346(14) ?
O8 C22 . 1.438(15) ?
O9 C32 . 1.252(15) ?
O10 C32 . 1.337(14) ?
O10 C33 . 1.465(13) ?
O11 C23 . 1.193(14) ?
O12 C40 . 1.437(13) ?
O12 H62 . 0.84 ?
O13 C29 . 1.422(12) ?
O13 H63 . 0.84 ?
O14 C33 . 1.375(13) ?
O14 H64 . 0.84 ?
C1 C2 . 1.437(16) ?
C2 C3 . 1.357(14) ?
C2 H29 . 0.95 ?
C3 C21 . 1.498(16) ?
C3 C4 . 1.520(16) ?
C4 C5 . 1.567(15) ?
C4 H27 . 1.0 ?
C5 C6 . 1.520(15) ?
C5 H2 . 0.99 ?
C5 H3 . 0.99 ?
C6 C12 . 1.540(14) ?
C6 C7 . 1.562(15) ?
C6 C17 . 1.579(14) ?
C7 C14 . 1.519(14) ?
C7 C8 . 1.534(14) ?
C7 H26 . 1.0 ?
C8 C9 . 1.533(16) ?
C8 H7 . 0.99 ?
C8 H25 . 0.99 ?
C9 C10 . 1.524(14) ?
C9 C13 . 1.580(15) ?
C9 H8 . 1.0 ?
C11 H24 . 0.98 ?
C11 H23 . 0.98 ?
C11 H1 . 0.98 ?
C12 H4 . 0.98 ?
C12 H6 . 0.98 ?
C12 H5 . 0.98 ?
C13 C20 . 1.530(17) ?
C13 C14 . 1.601(16) ?
C14 C15 . 1.532(15) ?
C14 C19 . 1.549(16) ?
C15 C16 . 1.516(17) ?
C15 H16 . 0.99 ?
C15 H9 . 0.99 ?
C16 C17 . 1.550(15) ?
C16 H15 . 0.99 ?
C16 H14 . 0.99 ?
C17 C18 . 1.502(18) ?
C17 H10 . 1.0 ?
C18 H13 . 0.98 ?
C18 H11 . 0.98 ?
C18 H12 . 0.98 ?
C19 H19 . 0.98 ?
C19 H17 . 0.98 ?
C19 H18 . 0.98 ?
C20 H22 . 0.98 ?
C20 H21 . 0.98 ?
C20 H20 . 0.98 ?
C21 H28 . 1.0 ?
C22 H51 . 0.98 ?
C22 H52 . 0.98 ?
C22 H30 . 0.98 ?
C23 C24 . 1.541(14) ?
C24 C25 . 1.548(15) ?
C24 C40 . 1.579(15) ?
C24 H48 . 1.0 ?
C25 C26 . 1.540(13) ?
C25 H50 . 0.99 ?
C25 H49 . 0.99 ?
C26 C34 . 1.541(15) ?
C26 C27 . 1.546(15) ?
C26 H53 . 1.0 ?
C27 C42 . 1.534(14) ?
C27 C38 . 1.551(14) ?
C27 C28 . 1.556(14) ?
C28 C29 . 1.537(15) ?
C28 H57 . 0.99 ?
C28 H33 . 0.99 ?
C29 C30 . 1.502(16) ?
C29 H32 . 1.0 ?
C30 C31 . 1.319(15) ?
C30 C33 . 1.509(15) ?
C31 C32 . 1.489(16) ?
C31 H58 . 0.95 ?
C33 H31 . 1.0 ?
C34 C35 . 1.530(16) ?
C34 C36 . 1.549(15) ?
C34 C40 . 1.565(16) ?
C35 H35 . 0.98 ?
C35 H36 . 0.98 ?
C35 H34 . 0.98 ?
C36 C37 . 1.54(2) ?
C36 H37 . 0.99 ?
C36 H44 . 0.99 ?
C37 C38 . 1.528(16) ?
C37 H39 . 0.99 ?
C37 H38 . 0.99 ?
C38 C39 . 1.551(17) ?
C38 H40 . 1.0 ?
C39 H42 . 0.98 ?
C39 H43 . 0.98 ?
C39 H41 . 0.98 ?
C40 C41 . 1.499(16) ?
C41 H46 . 0.98 ?
C41 H45 . 0.98 ?
C41 H47 . 0.98 ?
C42 H56 . 0.98 ?
C42 H54 . 0.98 ?
C42 H55 . 0.98 ?
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
O3 H59 O10 . 0.84 2.11 2.839(11) 145.7 ?
O4 H60 O9 . 0.84 2.04 2.789(11) 149.0 ?
O12 H62 O1 1_454 0.84 2.12 2.807(12) 138.1 ?
O13 H63 O6 1_454 0.84 2.13 2.842(12) 142.4 ?
O14 H64 O15 . 0.84 1.83 2.640(11) 160.3 ?
C2 H29 O15 . 0.95 2.64 3.405(14) 137.8 ?
C4 H27 O9 . 1.00 2.65 3.438(13) 136.3 ?
C21 H28 O5 1_656 1.00 2.35 3.320(14) 163.0 ?
C22 H30 O10 1_454 0.98 2.51 3.322(18) 140.5 ?
C31 H58 O16 1_454 0.95 2.62 3.377(15) 136.5 ?
C33 H31 O11 1_656 1.00 2.37 3.337(14) 162.1 ?
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
C21 O6 C1 O1 . . . . -176.4(10) ?
C21 O6 C1 C2 . . . . 0.7(12) ?
O1 C1 C2 C3 . . . . 176.8(12) ?
O6 C1 C2 C3 . . . . 0.2(13) ?
C1 C2 C3 C21 . . . . -1.0(12) ?
C1 C2 C3 C4 . . . . 175.3(10) ?
C2 C3 C4 O3 . . . . 1.4(15) ?
C21 C3 C4 O3 . . . . 177.3(9) ?
C2 C3 C4 C5 . . . . 123.4(11) ?
C21 C3 C4 C5 . . . . -60.7(13) ?
O3 C4 C5 C6 . . . . -92.5(10) ?
C3 C4 C5 C6 . . . . 144.4(9) ?
C4 C5 C6 C12 . . . . 171.9(9) ?
C4 C5 C6 C7 . . . . 48.5(12) ?
C4 C5 C6 C17 . . . . -70.1(12) ?
C5 C6 C7 C14 . . . . -167.9(9) ?
C12 C6 C7 C14 . . . . 73.6(12) ?
C17 C6 C7 C14 . . . . -48.6(11) ?
C5 C6 C7 C8 . . . . 64.4(11) ?
C12 C6 C7 C8 . . . . -54.1(12) ?
C17 C6 C7 C8 . . . . -176.3(8) ?
C14 C7 C8 C9 . . . . 36.5(10) ?
C6 C7 C8 C9 . . . . 170.5(9) ?
C7 C8 C9 C10 . . . . 114.6(10) ?
C7 C8 C9 C13 . . . . -9.4(11) ?
C11 O2 C10 O5 . . . . 1.3(17) ?
C11 O2 C10 C9 . . . . 176.5(10) ?
C8 C9 C10 O5 . . . . 167.6(11) ?
C13 C9 C10 O5 . . . . -69.5(14) ?
C8 C9 C10 O2 . . . . -7.5(14) ?
C13 C9 C10 O2 . . . . 115.4(10) ?
C10 C9 C13 O4 . . . . -30.3(12) ?
C8 C9 C13 O4 . . . . 99.8(10) ?
C10 C9 C13 C20 . . . . 87.2(11) ?
C8 C9 C13 C20 . . . . -142.6(10) ?
C10 C9 C13 C14 . . . . -149.3(9) ?
C8 C9 C13 C14 . . . . -19.2(11) ?
C8 C7 C14 C15 . . . . -171.7(9) ?
C6 C7 C14 C15 . . . . 53.7(12) ?
C8 C7 C14 C19 . . . . 65.6(11) ?
C6 C7 C14 C19 . . . . -69.0(12) ?
C8 C7 C14 C13 . . . . -47.9(10) ?
C6 C7 C14 C13 . . . . 177.5(9) ?
O4 C13 C14 C7 . . . . -78.4(10) ?
C20 C13 C14 C7 . . . . 162.5(10) ?
C9 C13 C14 C7 . . . . 40.5(10) ?
O4 C13 C14 C15 . . . . 41.6(12) ?
C20 C13 C14 C15 . . . . -77.6(13) ?
C9 C13 C14 C15 . . . . 160.5(9) ?
O4 C13 C14 C19 . . . . 161.8(8) ?
C20 C13 C14 C19 . . . . 42.7(13) ?
C9 C13 C14 C19 . . . . -79.2(10) ?
C7 C14 C15 C16 . . . . -52.9(12) ?
C19 C14 C15 C16 . . . . 73.8(11) ?
C13 C14 C15 C16 . . . . -166.6(9) ?
C14 C15 C16 C17 . . . . 54.7(12) ?
C15 C16 C17 C18 . . . . 176.0(10) ?
C15 C16 C17 C6 . . . . -52.5(13) ?
C5 C6 C17 C18 . . . . -65.4(12) ?
C12 C6 C17 C18 . . . . 49.7(13) ?
C7 C6 C17 C18 . . . . 174.0(9) ?
C5 C6 C17 C16 . . . . 166.1(9) ?
C12 C6 C17 C16 . . . . -78.9(12) ?
C7 C6 C17 C16 . . . . 45.4(11) ?
C1 O6 C21 O7 . . . . -120.4(10) ?
C1 O6 C21 C3 . . . . -1.2(12) ?
C2 C3 C21 O7 . . . . 119.6(10) ?
C4 C3 C21 O7 . . . . -57.0(13) ?
C2 C3 C21 O6 . . . . 1.4(12) ?
C4 C3 C21 O6 . . . . -175.2(9) ?
C22 O8 C23 O11 . . . . -1.1(17) ?
C22 O8 C23 C24 . . . . 175.7(10) ?
O11 C23 C24 C25 . . . . 172.2(10) ?
O8 C23 C24 C25 . . . . -4.6(13) ?
O11 C23 C24 C40 . . . . -66.4(13) ?
O8 C23 C24 C40 . . . . 116.8(10) ?
C23 C24 C25 C26 . . . . 115.3(10) ?
C40 C24 C25 C26 . . . . -5.4(10) ?
C24 C25 C26 C34 . . . . 32.1(10) ?
C24 C25 C26 C27 . . . . 167.9(8) ?
C25 C26 C27 C42 . . . . -55.5(12) ?
C34 C26 C27 C42 . . . . 72.9(12) ?
C25 C26 C27 C38 . . . . -179.5(8) ?
C34 C26 C27 C38 . . . . -51.1(11) ?
C25 C26 C27 C28 . . . . 61.7(11) ?
C34 C26 C27 C28 . . . . -169.9(9) ?
C42 C27 C28 C29 . . . . 174.0(9) ?
C26 C27 C28 C29 . . . . 50.5(11) ?
C38 C27 C28 C29 . . . . -65.9(11) ?
C27 C28 C29 O13 . . . . -91.8(10) ?
C27 C28 C29 C30 . . . . 146.6(9) ?
O13 C29 C30 C31 . . . . -1.6(16) ?
C28 C29 C30 C31 . . . . 119.5(13) ?
O13 C29 C30 C33 . . . . 175.6(9) ?
C28 C29 C30 C33 . . . . -63.3(12) ?
C29 C30 C31 C32 . . . . 176.8(11) ?
C33 C30 C31 C32 . . . . -0.6(13) ?
C33 O10 C32 O9 . . . . -177.8(11) ?
C33 O10 C32 C31 . . . . 1.5(13) ?
C30 C31 C32 O9 . . . . 178.6(13) ?
C30 C31 C32 O10 . . . . -0.5(14) ?
C32 O10 C33 O14 . . . . -121.0(10) ?
C32 O10 C33 C30 . . . . -1.7(11) ?
C31 C30 C33 O14 . . . . 122.1(11) ?
C29 C30 C33 O14 . . . . -55.6(13) ?
C31 C30 C33 O10 . . . . 1.4(12) ?
C29 C30 C33 O10 . . . . -176.3(9) ?
C25 C26 C34 C35 . . . . 69.1(11) ?
C27 C26 C34 C35 . . . . -66.2(12) ?
C25 C26 C34 C36 . . . . -170.2(9) ?
C27 C26 C34 C36 . . . . 54.5(12) ?
C25 C26 C34 C40 . . . . -47.3(10) ?
C27 C26 C34 C40 . . . . 177.4(9) ?
C35 C34 C36 C37 . . . . 70.9(11) ?
C26 C34 C36 C37 . . . . -52.8(11) ?
C40 C34 C36 C37 . . . . -167.1(9) ?
C34 C36 C37 C38 . . . . 58.8(12) ?
C36 C37 C38 C27 . . . . -58.8(13) ?
C36 C37 C38 C39 . . . . 173.7(9) ?
C42 C27 C38 C37 . . . . -75.9(12) ?
C26 C27 C38 C37 . . . . 49.6(11) ?
C28 C27 C38 C37 . . . . 169.1(9) ?
C42 C27 C38 C39 . . . . 49.7(13) ?
C26 C27 C38 C39 . . . . 175.2(8) ?
C28 C27 C38 C39 . . . . -65.2(11) ?
C35 C34 C40 O12 . . . . 163.1(9) ?
C26 C34 C40 O12 . . . . -76.8(10) ?
C36 C34 C40 O12 . . . . 41.0(13) ?
C35 C34 C40 C41 . . . . 44.5(13) ?
C26 C34 C40 C41 . . . . 164.6(10) ?
C36 C34 C40 C41 . . . . -77.6(14) ?
C35 C34 C40 C24 . . . . -78.1(10) ?
C26 C34 C40 C24 . . . . 42.0(9) ?
C36 C34 C40 C24 . . . . 159.8(9) ?
C23 C24 C40 O12 . . . . -31.5(12) ?
C25 C24 C40 O12 . . . . 94.9(10) ?
C23 C24 C40 C41 . . . . 86.3(11) ?
C25 C24 C40 C41 . . . . -147.3(10) ?
C23 C24 C40 C34 . . . . -148.9(9) ?
C25 C24 C40 C34 . . . . -22.5(10) ?
