#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/35/2013569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013569
loop_
_publ_author_name
'Mattia, Carlo Andrea'
'Braca, Alessandra'
'De Tommasi, Nunziatina'
'Puliti, Raffaella'
_publ_section_title
;
 A new norkaurane-γ-lactone from Parinari sprucei
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o644
_journal_page_last               o646
_journal_paper_doi               10.1107/S0108270103019814
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         '2(C20 H28 O6), H2 O'
_chemical_formula_sum            'C40 H58 O13'
_chemical_formula_weight         746.86
_chemical_name_systematic
;
10,13,16,17-tetrahydroxy-9-methyl-15-oxo-20-nor-kauran-18-oic
acid-γ-lactone
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.627(3)
_cell_length_b                   14.7157(19)
_cell_length_c                   21.081(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291.0(5)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      27.0
_cell_volume                     3606.9(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction
;
Structure Determination Package (Enraf--Nonius, 1985)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et. al., 1993)'
_diffrn_ambient_temperature      291.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method
'ω-2θ scans as suggested by peak-shape analysis'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4152
_diffrn_reflns_theta_full        74.84
_diffrn_reflns_theta_max         74.84
_diffrn_reflns_theta_min         3.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.231
_refine_ls_abs_structure_details
; The absolute configuration was chosen according to that of the known
bromine derivative of norkauren-γ-lactone (Garo et al., 1997) and is also
supported by the refined Flack parameter (Flack, 1983).
;
_refine_ls_abs_structure_Flack   0.04(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                3553
_reflns_number_total             4152
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa1027.cif
_cod_data_source_block           I
_cod_original_cell_volume        3607.0(11)
_cod_database_code               2013569
_cod_database_fobs_code          2013569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.09940(14) 0.50010(12) 0.38470(7) 0.0383(4) Uani d . 1 . . O
O2 0.0439(2) 0.50488(14) 0.06255(8) 0.0569(5) Uani d . 1 . . O
H1O 0.0816 0.4517 0.0477 0.085 Uiso calc R 1 . . H
O3 -0.21416(15) 0.50402(16) 0.23607(8) 0.0550(5) Uani d . 1 . . O
O4 -0.1140(2) 0.36981(15) 0.14609(11) 0.0687(6) Uani d . 1 . . O
H2O -0.1900 0.3530 0.1344 0.103 Uiso calc R 1 . . H
O6 0.11379(17) 0.54300(17) 0.48547(8) 0.0612(6) Uani d . 1 . . O
C1 -0.0464(2) 0.39808(16) 0.34619(11) 0.0401(5) Uani d . 1 . . C
H1A -0.1160 0.3914 0.3187 0.060 Uiso calc R 1 . . H
H1B 0.0101 0.3502 0.3336 0.060 Uiso calc R 1 . . H
C2 -0.0807(3) 0.3843(2) 0.41608(12) 0.0512(7) Uani d . 1 . . C
H2A -0.1364 0.3327 0.4186 0.077 Uiso calc R 1 . . H
H2B -0.0106 0.3665 0.4406 0.077 Uiso calc R 1 . . H
C3 -0.1349(2) 0.4680(2) 0.44769(12) 0.0491(6) Uani d . 1 . . C
H3A -0.2171 0.4733 0.4342 0.074 Uiso calc R 1 . . H
H3B -0.1335 0.4601 0.4948 0.074 Uiso calc R 1 . . H
C4 -0.0705(2) 0.55520(18) 0.42990(11) 0.0408(5) Uani d . 1 . . C
C5 -0.07694(19) 0.56657(16) 0.35691(10) 0.0354(5) Uani d . 1 . . C
H5 -0.1560 0.5501 0.3422 0.053 Uiso calc R 1 . . H
C6 -0.0471(3) 0.65943(17) 0.33247(11) 0.0491(7) Uani d . 1 . . C
H6A 0.0318 0.6765 0.3470 0.074 Uiso calc R 1 . . H
H6B -0.1026 0.7050 0.3498 0.074 Uiso calc R 1 . . H
C7 -0.0517(3) 0.66063(16) 0.25919(12) 0.0499(7) Uani d . 1 . . C
H7A -0.1312 0.6780 0.2457 0.075 Uiso calc R 1 . . H
H7B 0.0019 0.7088 0.2435 0.075 Uiso calc R 1 . . H
C8 -0.0203(2) 0.57105(14) 0.22747(10) 0.0327(4) Uani d . 1 . . C
C9 0.06334(19) 0.50929(15) 0.26801(10) 0.0334(4) Uani d . 1 . . C
C10 0.00729(18) 0.49281(15) 0.33555(9) 0.0301(4) Uani d . 1 . . C
C11 0.0828(2) 0.41999(17) 0.23172(10) 0.0382(5) Uani d . 1 . . C
H11A 0.0130 0.3809 0.2368 0.057 Uiso calc R 1 . . H
H11B 0.1490 0.3871 0.2514 0.057 Uiso calc R 1 . . H
C12 0.1073(2) 0.43221(18) 0.16004(11) 0.0434(5) Uani d . 1 . . C
H12A 0.1870 0.4564 0.1543 0.065 Uiso calc R 1 . . H
H12B 0.1030 0.3717 0.1385 0.065 Uiso calc R 1 . . H
C13 0.0224(2) 0.49649(17) 0.12925(10) 0.0393(5) Uani d . 1 . . C
C14 0.0297(2) 0.58705(17) 0.16089(10) 0.0418(5) Uani d . 1 . . C
H14A -0.0164 0.6334 0.1373 0.063 Uiso calc R 1 . . H
H14B 0.1113 0.6082 0.1635 0.063 Uiso calc R 1 . . H
C15 -0.1250(2) 0.51299(17) 0.20750(10) 0.0397(5) Uani d . 1 . . C
C16 -0.1020(2) 0.46725(19) 0.14227(11) 0.0461(6) Uani d D 1 . . C
C17A -0.1903(3) 0.4982(2) 0.09411(14) 0.0683(9) Uani d PD 0.80 A 1 C
H17A -0.1734 0.4678 0.0527 0.102 Uiso calc PR 0.80 A 1 H
H17B -0.2679 0.4773 0.1083 0.102 Uiso calc PR 0.80 A 1 H
O5A -0.1944(3) 0.5945(2) 0.08404(13) 0.0758(9) Uani d PDU 0.80 A 1 O
H3O -0.1441 0.6104 0.0503 0.114 Uiso calc PR 0.80 A 1 H
C17B -0.1903(3) 0.4982(2) 0.09411(14) 0.0683(9) Uani d PD 0.20 A 2 C
H17C -0.1867 0.5659 0.0908 0.102 Uiso calc PR 0.20 A 2 H
H17D -0.1690 0.4726 0.0517 0.102 Uiso calc PR 0.20 A 2 H
O5B -0.3064(4) 0.4722(10) 0.1083(5) 0.096(4) Uani d PDU 0.20 A 2 O
H4O -0.3152 0.4661 0.1529 0.144 Uiso calc PR 0.20 A 2 H
C18 0.0553(2) 0.53491(18) 0.43808(11) 0.0401(5) Uani d . 1 . . C
C19 -0.1091(3) 0.6363(2) 0.46970(12) 0.0602(8) Uani d . 1 . . C
H19A -0.1931 0.6472 0.4628 0.090 Uiso calc R 1 . . H
H19B -0.0648 0.6915 0.4567 0.090 Uiso calc R 1 . . H
H19C -0.0948 0.6233 0.5156 0.090 Uiso calc R 1 . . H
C20 0.1810(2) 0.5567(2) 0.27536(12) 0.0485(6) Uani d . 1 . . C
H20A 0.1707 0.6153 0.2987 0.073 Uiso calc R 1 . . H
H20B 0.2142 0.5691 0.2325 0.073 Uiso calc R 1 . . H
H20C 0.2343 0.5164 0.2997 0.073 Uiso calc R 1 . . H
O21 0.38029(14) 0.78946(13) 0.30019(7) 0.0406(4) Uani d . 1 . . O
O22 0.50877(16) 0.82283(13) -0.01270(7) 0.0450(4) Uani d . 1 . . O
H21O 0.5386 0.8783 -0.0289 0.068 Uiso calc R 1 . . H
O23 0.72687(14) 0.79774(14) 0.17847(8) 0.0461(4) Uani d . 1 . . O
O24 0.65908(17) 0.93747(12) 0.08694(8) 0.0469(4) Uani d . 1 . . O
H22O 0.7386 0.9503 0.0920 0.070 Uiso calc R 1 . . H
O26 0.33393(18) 0.73224(17) 0.39406(9) 0.0613(6) Uani d . 1 . . O
C21 0.5385(2) 0.89018(15) 0.28138(10) 0.0403(5) Uani d . 1 . . C
H21A 0.4879 0.9412 0.2671 0.060 Uiso calc R 1 . . H
H21B 0.6149 0.8976 0.2603 0.060 Uiso calc R 1 . . H
C22 0.5545(2) 0.89586(17) 0.35400(11) 0.0442(6) Uani d . 1 . . C
H22A 0.6116 0.9447 0.3638 0.066 Uiso calc R 1 . . H
H22B 0.4796 0.9135 0.3739 0.066 Uiso calc R 1 . . H
C23 0.5961(2) 0.80602(18) 0.38393(11) 0.0429(5) Uani d . 1 . . C
H23A 0.5824 0.8080 0.4308 0.064 Uiso calc R 1 . . H
H23B 0.6807 0.7995 0.3768 0.064 Uiso calc R 1 . . H
C24 0.5335(2) 0.72267(16) 0.35565(10) 0.0372(5) Uani d . 1 . . C
C25 0.56073(19) 0.72095(14) 0.28466(10) 0.0320(4) Uani d . 1 . . C
H25 0.6435 0.7368 0.2781 0.048 Uiso calc R 1 . . H
C26 0.5345(2) 0.63212(15) 0.25121(10) 0.0379(5) Uani d . 1 . . C
H26A 0.4514 0.6164 0.2570 0.057 Uiso calc R 1 . . H
H26B 0.5817 0.5822 0.2701 0.057 Uiso calc R 1 . . H
C27 0.5615(2) 0.64083(15) 0.18040(11) 0.0403(5) Uani d . 1 . . C
H27A 0.6444 0.6254 0.1739 0.060 Uiso calc R 1 . . H
H27B 0.5150 0.5946 0.1569 0.060 Uiso calc R 1 . . H
C28 0.53877(18) 0.73406(13) 0.15075(9) 0.0288(4) Uani d . 1 . . C
C29 0.44668(18) 0.79237(15) 0.18832(10) 0.0303(4) Uani d . 1 . . C
C30 0.48493(19) 0.79964(14) 0.26067(10) 0.0297(4) Uani d . 1 . . C
C31 0.4383(2) 0.88640(15) 0.15709(10) 0.0340(4) Uani d . 1 . . C
H31A 0.3688 0.9183 0.1739 0.051 Uiso calc R 1 . . H
H31B 0.5073 0.9229 0.1695 0.051 Uiso calc R 1 . . H
C32 0.4310(2) 0.88339(16) 0.08470(10) 0.0349(5) Uani d . 1 . . C
H32A 0.3527 0.8618 0.0721 0.052 Uiso calc R 1 . . H
H32B 0.4410 0.9463 0.0676 0.052 Uiso calc R 1 . . H
C33 0.5211(2) 0.82140(16) 0.05493(9) 0.0333(5) Uani d . 1 . . C
C34 0.5030(2) 0.72522(15) 0.08015(10) 0.0370(5) Uani d . 1 . . C
H34A 0.5529 0.6805 0.0573 0.055 Uiso calc R 1 . . H
H34B 0.4208 0.7061 0.0761 0.055 Uiso calc R 1 . . H
C35 0.64704(18) 0.79140(15) 0.14312(9) 0.0315(4) Uani d . 1 . . C
C36 0.64355(19) 0.84299(15) 0.07892(10) 0.0348(5) Uani d D 1 . . C
C37A 0.7377(2) 0.8086(2) 0.03447(11) 0.0547(7) Uani d PD 0.60 B 1 C
H37A 0.8127 0.8094 0.0577 0.082 Uiso calc PR 0.60 B 1 H
H37B 0.7206 0.7441 0.0230 0.082 Uiso calc PR 0.60 B 1 H
O25A 0.7492(3) 0.8590(3) -0.02109(14) 0.0641(9) Uani d PDU 0.60 B 1 O
H23O 0.7705 0.9195 -0.0108 0.096 Uiso calc PR 0.60 B 1 H
C37B 0.7377(2) 0.8086(2) 0.03447(11) 0.0547(7) Uani d PD 0.20 B 2 C
H37C 0.7158 0.8238 -0.0102 0.082 Uiso calc PR 0.20 B 2 H
H37D 0.8107 0.8416 0.0443 0.082 Uiso calc PR 0.20 B 2 H
O25B 0.7580(7) 0.7156(4) 0.0385(4) 0.063(2) Uani d PDU 0.20 B 2 O
H24O 0.8281 0.7014 0.0176 0.095 Uiso calc PR 0.20 B 2 H
C37C 0.7377(2) 0.8086(2) 0.03447(11) 0.0547(7) Uani d PD 0.20 B 3 C
H37E 0.7123 0.7495 0.0156 0.082 Uiso calc PR 0.20 B 3 H
H37F 0.7470 0.8530 -0.0011 0.082 Uiso calc PR 0.20 B 3 H
O25C 0.8439(4) 0.7960(10) 0.0635(4) 0.075(3) Uani d PDU 0.20 B 3 O
H25O 0.8426 0.7414 0.0876 0.112 Uiso calc PR 0.20 B 3 H
C38 0.4072(2) 0.74509(17) 0.35415(11) 0.0422(5) Uani d . 1 . . C
C39 0.5592(3) 0.6376(2) 0.39278(13) 0.0553(7) Uani d . 1 . . C
H39A 0.6439 0.6259 0.3922 0.083 Uiso calc R 1 . . H
H39B 0.5180 0.5850 0.3732 0.083 Uiso calc R 1 . . H
H39C 0.5328 0.6455 0.4376 0.083 Uiso calc R 1 . . H
C40 0.3272(2) 0.74649(19) 0.18324(12) 0.0455(6) Uani d . 1 . . C
H40A 0.3304 0.6848 0.2031 0.068 Uiso calc R 1 . . H
H40B 0.3053 0.7405 0.1376 0.068 Uiso calc R 1 . . H
H40C 0.2688 0.7845 0.2058 0.068 Uiso calc R 1 . . H
O1W 0.32631(19) 0.63066(16) 0.51173(9) 0.0617(5) Uani d G 1 . . O
H1W 0.2591 0.5946 0.5067 0.093 Uiso d G 1 . . H
H2W 0.3347 0.6696 0.4761 0.093 Uiso d G 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-6 0 7
-2 -8 -4
3 7 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C10 O1 C18 109.61(17) yes
C13 O2 H1O 109.5 ?
C16 O4 H2O 109.5 ?
C2 C1 C10 111.3(2) ?
C2 C1 H1A 109.4 ?
C10 C1 H1A 109.4 ?
C2 C1 H1B 109.4 ?
C10 C1 H1B 109.4 ?
H1A C1 H1B 108.0 ?
C3 C2 C1 114.6(2) ?
C3 C2 H2A 108.6 ?
C1 C2 H2A 108.6 ?
C3 C2 H2B 108.6 ?
C1 C2 H2B 108.6 ?
H2A C2 H2B 107.6 ?
C4 C3 C2 111.4(2) ?
C4 C3 H3A 109.3 ?
C2 C3 H3A 109.3 ?
C4 C3 H3B 109.3 ?
C2 C3 H3B 109.3 ?
H3A C3 H3B 108.0 ?
C18 C4 C19 112.2(2) ?
C18 C4 C3 106.3(2) ?
C19 C4 C3 112.2(2) ?
C5 C4 C18 100.49(19) yes
C5 C4 C19 116.6(2) yes
C3 C4 C5 108.1(2) ?
C6 C5 C10 113.4(2) ?
C6 C5 C4 115.34(19) ?
C10 C5 C4 100.65(17) ?
C6 C5 H5 109.0 ?
C10 C5 H5 109.0 ?
C4 C5 H5 109.0 ?
C5 C6 C7 110.2(2) ?
C5 C6 H6A 109.6 ?
C7 C6 H6A 109.6 ?
C5 C6 H6B 109.6 ?
C7 C6 H6B 109.6 ?
H6A C6 H6B 108.1 ?
C8 C7 C6 114.9(2) ?
C8 C7 H7A 108.5 ?
C6 C7 H7A 108.5 ?
C8 C7 H7B 108.5 ?
C6 C7 H7B 108.5 ?
H7A C7 H7B 107.5 ?
C7 C8 C9 114.06(19) yes
C7 C8 C14 111.04(18) ?
C7 C8 C15 114.2(2) yes
C14 C8 C15 97.68(17) yes
C14 C8 C9 110.42(18) ?
C15 C8 C9 108.30(17) ?
C11 C9 C20 107.8(2) ?
C11 C9 C8 108.22(17) ?
C20 C9 C8 109.85(18) ?
C11 C9 C10 112.13(17) ?
C20 C9 C10 110.09(18) ?
C8 C9 C10 108.70(17) ?
O1 C10 C5 101.77(16) ?
O1 C10 C1 104.72(16) ?
C5 C10 C1 109.81(19) ?
O1 C10 C9 108.50(16) ?
C1 C10 C9 115.79(18) yes
C5 C10 C9 114.78(17) yes
C9 C11 C12 114.42(19) ?
C9 C11 H11A 108.7 ?
C12 C11 H11A 108.7 ?
C9 C11 H11B 108.7 ?
C12 C11 H11B 108.7 ?
H11A C11 H11B 107.6 ?
C13 C12 C11 111.8(2) ?
C13 C12 H12A 109.3 ?
C11 C12 H12A 109.3 ?
C13 C12 H12B 109.3 ?
C11 C12 H12B 109.3 ?
H12A C12 H12B 107.9 ?
O2 C13 C14 110.6(2) ?
O2 C13 C12 111.1(2) ?
C14 C13 C12 109.2(2) ?
O2 C13 C16 111.4(2) ?
C14 C13 C16 102.9(2) yes
C12 C13 C16 111.3(2) ?
C13 C14 C8 104.46(18) ?
C13 C14 H14A 110.9 ?
C8 C14 H14A 110.9 ?
C13 C14 H14B 110.9 ?
C8 C14 H14B 110.9 ?
H14A C14 H14B 108.9 ?
O3 C15 C8 127.0(2) yes
O3 C15 C16 122.8(2) yes
C8 C15 C16 110.2(2) ?
O4 C16 C17A 105.7(2) ?
O4 C16 C13 112.3(2) ?
C17A C16 C13 115.8(2) ?
O4 C16 C15 111.4(2) ?
C17A C16 C15 110.3(2) ?
C13 C16 C15 101.5(2) yes
O5A C17A C16 114.8(3) ?
O5A C17A H17A 108.6 ?
C16 C17A H17A 108.6 ?
O5A C17A H17B 108.6 ?
C16 C17A H17B 108.6 ?
H17A C17A H17B 107.6 ?
O5B C17B C16 114.8(3) ?
O5B C17B H17C 108.5 ?
C16 C17B H17C 108.5 ?
O5B C17B H17D 108.5 ?
C16 C17B H17D 108.5 ?
H17C C17B H17D 107.5 ?
C17A O5A H3O 109.5 ?
C17B O5B H4O 109.5 ?
O1 C18 O6 120.9(2) yes
O6 C18 C4 128.3(2) yes
O1 C18 C4 110.65(19) ?
C4 C19 H19A 109.5 ?
C4 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C4 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
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 ?
C30 O21 C38 109.46(17) yes
C33 O22 H21O 109.5 ?
C36 O24 H22O 109.5 ?
C30 C21 C22 112.22(19) ?
C30 C21 H21A 109.2 ?
C22 C21 H21A 109.2 ?
C30 C21 H21B 109.2 ?
C22 C21 H21B 109.2 ?
H21A C21 H21B 107.9 ?
C23 C22 C21 113.38(19) ?
C23 C22 H22A 108.9 ?
C21 C22 H22A 108.9 ?
C23 C22 H22B 108.9 ?
C21 C22 H22B 108.9 ?
H22A C22 H22B 107.7 ?
C22 C23 C24 112.0(2) ?
C22 C23 H23A 109.2 ?
C24 C23 H23A 109.2 ?
C22 C23 H23B 109.2 ?
C24 C23 H23B 109.2 ?
H23A C23 H23B 107.9 ?
C38 C24 C39 112.8(2) ?
C25 C24 C38 100.68(18) yes
C25 C24 C39 117.0(2) yes
C38 C24 C23 107.1(2) ?
C39 C24 C23 111.4(2) ?
C25 C24 C23 107.03(19) ?
C26 C25 C24 115.31(19) ?
C26 C25 C30 112.33(18) ?
C24 C25 C30 100.96(17) ?
C26 C25 H25 109.3 ?
C24 C25 H25 109.3 ?
C30 C25 H25 109.3 ?
C25 C26 C27 109.87(19) ?
C25 C26 H26A 109.7 ?
C27 C26 H26A 109.7 ?
C25 C26 H26B 109.7 ?
C27 C26 H26B 109.7 ?
H26A C26 H26B 108.2 ?
C28 C27 C26 115.95(19) ?
C28 C27 H27A 108.3 ?
C26 C27 H27A 108.3 ?
C28 C27 H27B 108.3 ?
C26 C27 H27B 108.3 ?
H27A C27 H27B 107.4 ?
C27 C28 C29 113.46(18) yes
C27 C28 C35 113.36(19) yes
C34 C28 C35 99.58(16) yes
C27 C28 C34 111.29(17) ?
C35 C28 C29 108.13(16) ?
C34 C28 C29 110.14(17) ?
C31 C29 C40 107.87(18) ?
C31 C29 C28 108.44(17) ?
C40 C29 C28 109.60(19) ?
C31 C29 C30 111.58(17) ?
C40 C29 C30 110.25(17) ?
C28 C29 C30 109.06(16) ?
O21 C30 C21 105.12(17) ?
O21 C30 C25 102.06(16) ?
C21 C30 C25 109.10(18) ?
O21 C30 C29 107.60(17) yes
C21 C30 C29 116.38(17) ?
C25 C30 C29 115.07(17) yes
C32 C31 C29 113.92(18) ?
C32 C31 H31A 108.8 ?
C29 C31 H31A 108.8 ?
C32 C31 H31B 108.8 ?
C29 C31 H31B 108.8 ?
H31A C31 H31B 107.7 ?
C33 C32 C31 112.92(18) ?
C33 C32 H32A 109.0 ?
C31 C32 H32A 109.0 ?
C33 C32 H32B 109.0 ?
C31 C32 H32B 109.0 ?
H32A C32 H32B 107.8 ?
O22 C33 C32 109.38(18) ?
O22 C33 C34 110.26(18) ?
C32 C33 C34 108.47(18) ?
O22 C33 C36 114.53(18) ?
C32 C33 C36 112.08(18) ?
C34 C33 C36 101.76(18) yes
C33 C34 C28 102.68(16) ?
C33 C34 H34A 111.2 ?
C28 C34 H34A 111.2 ?
C33 C34 H34B 111.2 ?
C28 C34 H34B 111.2 ?
H34A C34 H34B 109.1 ?
O23 C35 C28 128.3(2) yes
O23 C35 C36 121.8(2) yes
C28 C35 C36 109.95(17) ?
O24 C36 C37A 107.95(19) ?
O24 C36 C33 111.09(19) ?
C37A C36 C33 113.06(18) ?
O24 C36 C35 111.95(18) ?
C37A C36 C35 110.74(16) ?
C33 C36 C35 102.06(17) yes
O25A C37A C36 114.1(2) ?
O25A C37A H37A 108.7 ?
C36 C37A H37A 108.7 ?
O25A C37A H37B 108.7 ?
C36 C37A H37B 108.7 ?
H37A C37A H37B 107.6 ?
O25B C37B C36 114.2(2) ?
O25B C37B H37C 108.7 ?
C36 C37B H37C 108.7 ?
O25B C37B H37D 108.7 ?
C36 C37B H37D 108.7 ?
H37C C37B H37D 107.6 ?
O25C C37C C36 114.3(2) ?
O25C C37C H37E 108.7 ?
C36 C37C H37E 108.7 ?
O25C C37C H37F 108.7 ?
C36 C37C H37F 108.7 ?
H37E C37C H37F 107.6 ?
C37A O25A H23O 109.5 ?
C37B O25B H24O 109.5 ?
C37C O25C H25O 109.5 ?
O26 C38 O21 119.9(2) yes
O26 C38 C24 129.5(2) yes
O21 C38 C24 110.47(19) ?
C24 C39 H39A 109.5 ?
C24 C39 H39B 109.5 ?
H39A C39 H39B 109.5 ?
C24 C39 H39C 109.5 ?
H39A C39 H39C 109.5 ?
H39B C39 H39C 109.5 ?
C29 C40 H40A 109.5 ?
C29 C40 H40B 109.5 ?
H40A C40 H40B 109.5 ?
C29 C40 H40C 109.5 ?
H40A C40 H40C 109.5 ?
H40B C40 H40C 109.5 ?
H1W O1W H2W 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 C10 . 1.494(2) yes
O1 C18 . 1.339(3) yes
O2 C13 . 1.434(3) yes
O2 H1O . 0.9500 ?
O3 C15 . 1.206(3) yes
O4 C16 . 1.443(3) yes
O4 H2O . 0.9500 ?
O6 C18 . 1.215(3) yes
C1 C2 . 1.540(3) ?
C1 C10 . 1.544(3) ?
C1 H1A . 1.0000 ?
C1 H1B . 1.0000 ?
C2 C3 . 1.536(4) ?
C2 H2A . 1.0000 ?
C2 H2B . 1.0000 ?
C3 C4 . 1.533(4) ?
C3 H3A . 1.0000 ?
C3 H3B . 1.0000 ?
C4 C18 . 1.503(3) ?
C4 C19 . 1.526(4) ?
C4 C5 . 1.550(3) ?
C5 C6 . 1.501(3) ?
C5 C10 . 1.530(3) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.546(3) ?
C6 H6A . 1.0000 ?
C6 H6B . 1.0000 ?
C7 C8 . 1.523(3) ?
C7 H7A . 1.0000 ?
C7 H7B . 1.0000 ?
C8 C9 . 1.582(3) yes
C8 C14 . 1.537(3) ?
C8 C15 . 1.546(3) yes
C9 C10 . 1.585(3) yes
C9 C11 . 1.537(3) ?
C9 C20 . 1.543(3) ?
C11 C12 . 1.548(3) ?
C11 H11A . 1.0000 ?
C11 H11B . 1.0000 ?
C12 C13 . 1.513(3) ?
C12 H12A . 1.0000 ?
C12 H12B . 1.0000 ?
C13 C14 . 1.493(3) ?
C13 C16 . 1.534(4) ?
C14 H14A . 1.0000 ?
C14 H14B . 1.0000 ?
C15 C16 . 1.554(3) yes
C16 C17A . 1.514(4) yes
C16 C17B . 1.514(4) ?
C17A O5A . 1.434(4) yes
C17A H17A . 1.0000 ?
C17A H17B . 1.0000 ?
C17B O5B . 1.435(7) ?
C17B H17C . 1.0000 ?
C17B H17D . 1.0000 ?
O5A H3O . 0.9500 ?
O5B H4O . 0.9500 ?
C19 H19A . 1.0000 ?
C19 H19B . 1.0000 ?
C19 H19C . 1.0000 ?
C20 H20A . 1.0000 ?
C20 H20B . 1.0000 ?
C20 H20C . 1.0000 ?
O21 C30 . 1.482(2) yes
O21 C38 . 1.348(3) yes
O22 C33 . 1.433(2) yes
O22 H21O . 0.9500 ?
O23 C35 . 1.194(3) yes
O24 C36 . 1.412(3) yes
O24 H22O . 0.9500 ?
O26 C38 . 1.212(3) yes
C21 C22 . 1.545(3) ?
C21 C30 . 1.534(3) ?
C21 H21A . 1.0000 ?
C21 H21B . 1.0000 ?
C22 C23 . 1.543(3) ?
C22 H22A . 1.0000 ?
C22 H22B . 1.0000 ?
C23 C24 . 1.546(3) ?
C23 H23A . 1.0000 ?
C23 H23B . 1.0000 ?
C24 C25 . 1.530(3) ?
C24 C38 . 1.506(4) ?
C24 C39 . 1.506(3) ?
C25 C26 . 1.516(3) ?
C25 C30 . 1.541(3) ?
C25 H25 . 1.0000 ?
C26 C27 . 1.531(3) ?
C26 H26A . 1.0000 ?
C26 H26B . 1.0000 ?
C27 C28 . 1.531(3) ?
C27 H27A . 1.0000 ?
C27 H27B . 1.0000 ?
C28 C29 . 1.584(3) yes
C28 C34 . 1.551(3) ?
C28 C35 . 1.524(3) yes
C29 C30 . 1.592(3) yes
C29 C31 . 1.535(3) ?
C29 C40 . 1.548(3) ?
C31 C32 . 1.529(3) ?
C31 H31A . 1.0000 ?
C31 H31B . 1.0000 ?
C32 C33 . 1.525(3) ?
C32 H32A . 1.0000 ?
C32 H32B . 1.0000 ?
C33 C34 . 1.526(3) ?
C33 C36 . 1.544(3) ?
C34 H34A . 1.0000 ?
C34 H34B . 1.0000 ?
C35 C36 . 1.552(3) yes
C36 C37A . 1.527(3) yes
C36 C37B . 1.527(3) ?
C36 C37C . 1.527(3) ?
C37A O25A . 1.393(3) yes
C37A H37A . 1.0000 ?
C37A H37B . 1.0000 ?
C37B O25B . 1.391(6) ?
C37B H37C . 1.0000 ?
C37B H37D . 1.0000 ?
C37C O25C . 1.392(6) ?
C37C H37E . 1.0000 ?
C37C H37F . 1.0000 ?
O25A H23O . 0.9500 ?
O25B H24O . 0.9500 ?
O25C H25O . 0.9500 ?
C39 H39A . 1.0000 ?
C39 H39B . 1.0000 ?
C39 H39C . 1.0000 ?
C40 H40A . 1.0000 ?
C40 H40B . 1.0000 ?
C40 H40C . 1.0000 ?
O1W H1W . 0.9500 ?
O1W H2W . 0.9500 ?
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
O2 H1O O1W 2_564 0.95 1.79 2.720(3) 167.3 yes
O4 H2O O21 4_545 0.95 2.77 3.503(3) 134.6 yes
O4 H2O O26 4_545 0.95 2.51 3.370(3) 149.9 yes
O5A H3O O2 . 0.95 2.69 3.102(4) 106.6 yes
O5A H3O O22 3_465 0.95 2.18 3.053(4) 152.1 yes
O5B H4O O3 . 0.95 2.18 2.937(10) 135.4 yes
O5B H4O O21 4_545 0.95 2.88 3.420(12) 117.0 yes
O22 H21O O2 3_565 0.95 1.86 2.775(3) 160.5 yes
O22 H21O O25A . 0.95 2.47 2.851(4) 103.8 yes
O24 H22O O1 4_655 0.95 2.08 3.015(2) 168.0 yes
O24 H22O O6 4_655 0.95 2.73 3.423(3) 130.0 yes
O25A H23O O6 4_655 0.95 2.32 3.230(5) 159.6 yes
O25B H24O O22 3_565 0.95 2.13 3.020(7) 154.8 yes
O25C H25O O5A 1_655 0.95 2.21 3.029(15) 144.5 yes
O25C H25O O23 . 0.95 2.48 2.780(8) 98.0 yes
O1W H1W O6 . 0.95 1.91 2.842(3) 167.8 yes
O1W H2W O26 . 0.95 1.96 2.898(3) 168.8 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
C10 C1 C2 C3 40.4(3)
C1 C2 C3 C4 -42.7(3)
C2 C3 C4 C18 -46.8(3)
C2 C3 C4 C19 -169.8(2)
C2 C3 C4 C5 60.4(3)
C18 C4 C5 C6 -84.7(3)
C19 C4 C5 C6 36.9(3)
C3 C4 C5 C6 164.2(2)
C18 C4 C5 C10 37.8(2)
C19 C4 C5 C10 159.3(2)
C3 C4 C5 C10 -73.4(2)
C10 C5 C6 C7 62.3(3)
C4 C5 C6 C7 177.6(2)
C5 C6 C7 C8 -31.3(4)
C6 C7 C8 C14 -152.4(3)
C6 C7 C8 C15 98.4(3)
C6 C7 C8 C9 -26.8(3)
C7 C8 C9 C11 177.4(2)
C14 C8 C9 C11 -56.8(2)
C15 C8 C9 C11 49.1(2)
C7 C8 C9 C20 -65.1(3)
C14 C8 C9 C20 60.7(2)
C15 C8 C9 C20 166.58(19)
C7 C8 C9 C10 55.4(3)
C14 C8 C9 C10 -178.77(18)
C15 C8 C9 C10 -72.9(2)
C18 O1 C10 C5 25.4(2)
C18 O1 C10 C1 -88.9(2)
C18 O1 C10 C9 146.85(19)
C6 C5 C10 O1 85.3(2)
C4 C5 C10 O1 -38.5(2)
C6 C5 C10 C1 -164.18(19)
C4 C5 C10 C1 72.0(2)
C6 C5 C10 C9 -31.7(3)
C4 C5 C10 C9 -155.45(18)
C2 C1 C10 O1 51.5(3)
C2 C1 C10 C5 -57.1(3)
C2 C1 C10 C9 170.9(2)
C11 C9 C10 O1 101.9(2)
C20 C9 C10 O1 -18.1(2)
C8 C9 C10 O1 -138.47(18)
C11 C9 C10 C5 -145.03(19)
C20 C9 C10 C5 94.9(2)
C8 C9 C10 C5 -25.4(2)
C11 C9 C10 C1 -15.4(3)
C20 C9 C10 C1 -135.4(2)
C8 C9 C10 C1 104.2(2)
C20 C9 C11 C12 -73.6(2)
C8 C9 C11 C12 45.1(3)
C10 C9 C11 C12 165.01(19)
C9 C11 C12 C13 -47.6(3)
C11 C12 C13 O2 -178.2(2)
C11 C12 C13 C14 59.6(3)
C11 C12 C13 C16 -53.4(3)
O2 C13 C14 C8 168.1(2)
C12 C13 C14 C8 -69.3(2)
C16 C13 C14 C8 49.0(2)
C7 C8 C14 C13 -163.4(2)
C15 C8 C14 C13 -43.7(2)
C9 C8 C14 C13 69.1(2)
C7 C8 C15 O3 -37.7(3)
C14 C8 C15 O3 -154.9(3)
C9 C8 C15 O3 90.5(3)
C7 C8 C15 C16 140.8(2)
C14 C8 C15 C16 23.6(2)
C9 C8 C15 C16 -91.0(2)
O2 C13 C16 O4 91.2(3)
C14 C13 C16 O4 -150.2(2)
C12 C13 C16 O4 -33.4(3)
O2 C13 C16 C17A -30.3(3)
C14 C13 C16 C17A 88.2(3)
C12 C13 C16 C17A -154.9(2)
O2 C13 C16 C15 -149.7(2)
C14 C13 C16 C15 -31.2(2)
C12 C13 C16 C15 85.7(2)
O3 C15 C16 O4 -57.8(3)
C8 C15 C16 O4 123.6(2)
O3 C15 C16 C17A 59.3(3)
C8 C15 C16 C17A -119.3(2)
O3 C15 C16 C13 -177.5(2)
C8 C15 C16 C13 3.9(2)
O4 C16 C17A O5A 178.8(3)
C13 C16 C17A O5A -56.2(4)
C15 C16 C17A O5A 58.3(3)
O4 C16 C17B O5B 56.7(8)
C13 C16 C17B O5B -178.2(7)
C15 C16 C17B O5B -63.8(7)
C10 O1 C18 O6 176.6(2)
C10 O1 C18 C4 -0.5(3)
C19 C4 C18 O6 34.5(4)
C3 C4 C18 O6 -88.5(3)
C5 C4 C18 O6 159.0(3)
C19 C4 C18 O1 -148.7(2)
C3 C4 C18 O1 88.3(2)
C5 C4 C18 O1 -24.2(3)
C30 C21 C22 C23 40.0(3)
C21 C22 C23 C24 -42.2(3)
C22 C23 C24 C38 -46.3(2)
C22 C23 C24 C39 -170.0(2)
C22 C23 C24 C25 60.9(3)
C38 C24 C25 C26 -83.8(2)
C39 C24 C25 C26 38.8(3)
C23 C24 C25 C26 164.5(2)
C38 C24 C25 C30 37.6(2)
C39 C24 C25 C30 160.1(2)
C23 C24 C25 C30 -74.2(2)
C24 C25 C26 C27 178.0(2)
C30 C25 C26 C27 63.0(3)
C25 C26 C27 C28 -34.5(3)
C26 C27 C28 C35 100.2(2)
C26 C27 C28 C34 -148.6(2)
C26 C27 C28 C29 -23.7(3)
C35 C28 C29 C31 49.1(2)
C27 C28 C29 C31 175.73(18)
C34 C28 C29 C31 -58.8(2)
C35 C28 C29 C40 166.60(16)
C27 C28 C29 C40 -66.7(2)
C34 C28 C29 C40 58.8(2)
C35 C28 C29 C30 -72.6(2)
C27 C28 C29 C30 54.0(2)
C34 C28 C29 C30 179.53(16)
C38 O21 C30 C21 -90.0(2)
C38 O21 C30 C25 23.9(2)
C38 O21 C30 C29 145.4(2)
C22 C21 C30 O21 51.9(2)
C22 C21 C30 C25 -56.9(3)
C22 C21 C30 C29 170.8(2)
C26 C25 C30 O21 85.5(2)
C24 C25 C30 O21 -37.9(2)
C26 C25 C30 C21 -163.60(19)
C24 C25 C30 C21 73.0(2)
C26 C25 C30 C29 -30.7(3)
C24 C25 C30 C29 -154.05(18)
C31 C29 C30 O21 101.00(19)
C40 C29 C30 O21 -18.8(2)
C28 C29 C30 O21 -139.23(17)
C31 C29 C30 C21 -16.6(3)
C40 C29 C30 C21 -136.4(2)
C28 C29 C30 C21 103.2(2)
C31 C29 C30 C25 -146.01(19)
C40 C29 C30 C25 94.1(2)
C28 C29 C30 C25 -26.2(2)
C40 C29 C31 C32 -72.9(2)
C28 C29 C31 C32 45.8(2)
C30 C29 C31 C32 165.90(18)
C29 C31 C32 C33 -47.9(3)
C31 C32 C33 O22 -179.67(19)
C31 C32 C33 C34 60.0(2)
C31 C32 C33 C36 -51.5(3)
O22 C33 C34 C28 171.19(18)
C32 C33 C34 C28 -69.1(2)
C36 C33 C34 C28 49.3(2)
C35 C28 C34 C33 -43.3(2)
C27 C28 C34 C33 -163.1(2)
C29 C28 C34 C33 70.2(2)
C27 C28 C35 O23 -38.4(3)
C34 C28 C35 O23 -156.7(2)
C29 C28 C35 O23 88.3(3)
C27 C28 C35 C36 140.27(18)
C34 C28 C35 C36 22.0(2)
C29 C28 C35 C36 -93.02(19)
O22 C33 C36 O24 87.8(2)
C32 C33 C36 O24 -37.5(2)
C34 C33 C36 O24 -153.22(18)
O22 C33 C36 C37A -33.7(3)
C32 C33 C36 C37A -159.06(17)
C34 C33 C36 C37A 85.24(19)
O22 C33 C36 C35 -152.68(18)
C32 C33 C36 C35 82.0(2)
C34 C33 C36 C35 -33.7(2)
O23 C35 C36 O24 -55.4(3)
C28 C35 C36 O24 125.84(19)
O23 C35 C36 C37A 65.1(3)
C28 C35 C36 C37A -113.6(2)
O23 C35 C36 C33 -174.3(2)
C28 C35 C36 C33 7.0(2)
O24 C36 C37A O25A -49.7(3)
C33 C36 C37A O25A 73.6(3)
C35 C36 C37A O25A -172.6(3)
O24 C36 C37B O25B 159.4(5)
C33 C36 C37B O25B -77.3(5)
C35 C36 C37B O25B 36.6(6)
O24 C36 C37C O25C 79.8(7)
C33 C36 C37C O25C -156.9(7)
C35 C36 C37C O25C -43.1(7)
C30 O21 C38 O26 177.7(2)
C30 O21 C38 C24 0.7(3)
C39 C24 C38 O26 32.9(4)
C25 C24 C38 O26 158.3(3)
C23 C24 C38 O26 -90.0(3)
C39 C24 C38 O21 -150.5(2)
C25 C24 C38 O21 -25.1(3)
C23 C24 C38 O21 86.6(2)
