#------------------------------------------------------------------------------
#$Date: 2020-10-22 02:23:33 +0300 (Thu, 22 Oct 2020) $
#$Revision: 258534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038909.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_4038909
loop_
_publ_author_name
'Zhao, Yinjiao'
'Li, Yuda'
'Wang, Bei'
'Zhao, Jingfeng'
'Li, Liang'
'Luo, Xiao-Dong'
'Zhang, Hongbin'
_publ_section_title
;
 Total Synthesis of Dactylicapnosines A and B.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01900
_journal_year                    2020
_chemical_formula_moiety         'C25 H29 N O9, C H4 O'
_chemical_formula_sum            'C26 H33 N O10'
_chemical_formula_weight         519.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.273(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7326(16)
_cell_length_b                   9.2331(11)
_cell_length_c                   19.795(2)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.44
_cell_volume                     2502.9(5)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27387
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.211
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          1.080
_exptl_crystal_size_mid          0.780
_exptl_crystal_size_min          0.480
_exptl_transmission_factor_max   0.4940
_exptl_transmission_factor_min   0.4031
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.075
_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     364
_refine_ls_number_reflns         7509
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0693P)²+0.4357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5933
_reflns_number_total             7509
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01900_si_002.cif
_cod_data_source_block           mo_zhb_zyj1_0m
_cod_original_cell_volume        2503.0(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038909
_shelx_shelxl_version_number     2014/7
_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   0.894
_shelx_estimated_absorpt_t_max   0.951
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.15449(6) 0.41183(10) -0.12084(4) 0.01968(18) Uani 1 1 d . . . . .
O2 O 0.61181(6) 0.80568(11) 0.01392(5) 0.0303(2) Uani 1 1 d . . . . .
O3 O 0.53517(6) 0.56062(9) 0.07603(4) 0.01953(18) Uani 1 1 d . . . . .
O4 O 0.32746(6) 0.79370(8) 0.05781(4) 0.01721(17) Uani 1 1 d . . . . .
C25 C 0.21193(11) 0.4818(2) -0.22378(7) 0.0360(3) Uani 1 1 d . . . . .
H27 H 0.2267 0.5768 -0.2035 0.054 Uiso 1 1 calc R U . . .
H28 H 0.1990 0.4925 -0.2729 0.054 Uiso 1 1 calc R U . . .
H29 H 0.2678 0.4169 -0.2143 0.054 Uiso 1 1 calc R U . . .
O6 O 0.01281(6) 0.30988(9) -0.09142(4) 0.02065(18) Uani 1 1 d . . . . .
O7 O 0.35130(7) 0.46164(10) 0.28464(4) 0.02432(19) Uani 1 1 d . . . . .
O8 O 0.42789(6) 0.65030(9) 0.19596(4) 0.01899(17) Uani 1 1 d . . . . .
O9 O 0.31010(7) 0.77443(11) -0.11499(5) 0.0289(2) Uani 1 1 d . . . . .
O10 O 0.48793(6) 0.88903(11) -0.10231(5) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.12966(7) 0.38549(11) -0.01117(5) 0.01601(19) Uani 1 1 d . . . . .
C1 C 0.03639(10) 0.52142(15) -0.20463(7) 0.0278(3) Uani 1 1 d . . . . .
H5 H -0.0218 0.4762 -0.1879 0.042 Uiso 1 1 calc R U . . .
H4 H 0.0244 0.5427 -0.2530 0.042 Uiso 1 1 calc R U . . .
H1 H 0.0509 0.6116 -0.1798 0.042 Uiso 1 1 calc R U . . .
C2 C 0.12273(9) 0.41860(13) -0.19391(6) 0.0201(2) Uani 1 1 d . . . . .
C3 C 0.09264(8) 0.36475(12) -0.07601(6) 0.0164(2) Uani 1 1 d . . . . .
C4 C 0.22066(7) 0.46680(12) 0.00529(5) 0.0138(2) Uani 1 1 d . . . . .
H20 H 0.2721 0.4265 -0.0226 0.017 Uiso 1 1 calc R U . . .
C5 C 0.20899(8) 0.62986(12) -0.01137(6) 0.0159(2) Uani 1 1 d . . . . .
H21 H 0.1831 0.6426 -0.0590 0.019 Uiso 1 1 calc R U . . .
H22 H 0.1627 0.6749 0.0184 0.019 Uiso 1 1 calc R U . . .
C6 C 0.30839(8) 0.70088(12) -0.00026(5) 0.0146(2) Uani 1 1 d . . . . .
C7 C 0.37259(8) 0.65157(11) 0.05883(5) 0.0138(2) Uani 1 1 d . . . . .
C8 C 0.48031(8) 0.65205(12) 0.05028(6) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.51665(8) 0.76573(13) 0.00501(6) 0.0188(2) Uani 1 1 d . . . . .
C10 C 0.65075(10) 0.82889(15) 0.08265(8) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.6013 0.8761 0.1083 0.047 Uiso 1 1 calc R U . . .
H26 H 0.7087 0.8908 0.0828 0.047 Uiso 1 1 calc R U . . .
H3 H 0.6687 0.7356 0.1036 0.047 Uiso 1 1 calc R U . . .
C11 C 0.09971(11) 0.26835(15) -0.22215(7) 0.0291(3) Uani 1 1 d . . . . .
H6 H 0.1529 0.2020 -0.2077 0.044 Uiso 1 1 calc R U . . .
H7 H 0.0927 0.2727 -0.2717 0.044 Uiso 1 1 calc R U . . .
H8 H 0.0387 0.2335 -0.2052 0.044 Uiso 1 1 calc R U . . .
C12 C 0.07060(8) 0.33858(13) 0.04331(6) 0.0194(2) Uani 1 1 d . . . . .
H18 H 0.0172 0.2749 0.0247 0.023 Uiso 1 1 calc R U . . .
H19 H 0.0410 0.4240 0.0641 0.023 Uiso 1 1 calc R U . . .
C13 C 0.13436(8) 0.25704(13) 0.09677(6) 0.0198(2) Uani 1 1 d . . . . .
H17 H 0.0948 0.2264 0.1341 0.024 Uiso 1 1 calc R U . . .
H16 H 0.1619 0.1694 0.0766 0.024 Uiso 1 1 calc R U . . .
C14 C 0.21538(8) 0.35512(12) 0.12367(6) 0.0155(2) Uani 1 1 d . . . . .
C15 C 0.24717(8) 0.35452(12) 0.19245(6) 0.0175(2) Uani 1 1 d . . . . .
H15 H 0.2192 0.2881 0.2221 0.021 Uiso 1 1 calc R U . . .
C16 C 0.31920(8) 0.44979(13) 0.21797(5) 0.0175(2) Uani 1 1 d . . . . .
C17 C 0.30786(11) 0.36682(16) 0.33118(7) 0.0312(3) Uani 1 1 d . . . . .
H10 H 0.2370 0.3813 0.3279 0.047 Uiso 1 1 calc R U . . .
H9 H 0.3345 0.3882 0.3774 0.047 Uiso 1 1 calc R U . . .
H11 H 0.3224 0.2661 0.3200 0.047 Uiso 1 1 calc R U . . .
C18 C 0.36196(8) 0.54529(12) 0.17344(6) 0.0158(2) Uani 1 1 d . . . . .
C19 C 0.51789(9) 0.59683(15) 0.22903(7) 0.0246(3) Uani 1 1 d . . . . .
H13 H 0.5065 0.5654 0.2751 0.037 Uiso 1 1 calc R U . . .
H12 H 0.5670 0.6741 0.2311 0.037 Uiso 1 1 calc R U . . .
H14 H 0.5413 0.5147 0.2034 0.037 Uiso 1 1 calc R U . . .
C20 C 0.33091(8) 0.54467(12) 0.10502(5) 0.0141(2) Uani 1 1 d . . . . .
C21 C 0.25589(8) 0.45134(11) 0.07950(5) 0.0139(2) Uani 1 1 d . . . . .
C22 C 0.35624(8) 0.75958(12) -0.06097(6) 0.0170(2) Uani 1 1 d . . . . .
C23 C 0.46023(8) 0.80693(12) -0.05055(6) 0.0185(2) Uani 1 1 d . . . . .
C24 C 0.58527(9) 0.87196(17) -0.12262(7) 0.0307(3) Uani 1 1 d . . . . .
H25 H 0.6304 0.9296 -0.0929 0.046 Uiso 1 1 calc R U . . .
H24 H 0.5880 0.9050 -0.1695 0.046 Uiso 1 1 calc R U . . .
H23 H 0.6040 0.7696 -0.1194 0.046 Uiso 1 1 calc R U . . .
O1S O 0.99466(16) -0.0237(2) 0.05953(14) 0.0466(8) Uani 0.518(4) 1 d D U P A 1
H1S H 0.9969 -0.1136 0.0658 0.070 Uiso 0.518(4) 1 calc R U P A 1
C1S C 0.8981(3) 0.0261(6) 0.0651(4) 0.0597(15) Uani 0.518(4) 1 d D U P A 1
H1S1 H 0.8993 0.1108 0.0950 0.090 Uiso 0.518(4) 1 calc R U P A 1
H1S2 H 0.8593 -0.0510 0.0840 0.090 Uiso 0.518(4) 1 calc R U P A 1
H1S3 H 0.8690 0.0529 0.0201 0.090 Uiso 0.518(4) 1 calc R U P A 1
O1SA O 0.8553(2) 0.0233(3) 0.02993(13) 0.0387(7) Uani 0.482(4) 1 d D U P A 2
H1SA H 0.8997 0.0191 0.0030 0.058 Uiso 0.482(4) 1 calc R U P A 2
C1SA C 0.8973(4) 0.0441(6) 0.0966(2) 0.0341(10) Uani 0.482(4) 1 d D U P A 2
H1S4 H 0.9491 -0.0275 0.1064 0.051 Uiso 0.482(4) 1 calc R U P A 2
H1S5 H 0.8471 0.0325 0.1288 0.051 Uiso 0.482(4) 1 calc R U P A 2
H1S6 H 0.9250 0.1418 0.1008 0.051 Uiso 0.482(4) 1 calc R 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 120.23(9) . . ?
C9 O2 C10 116.71(11) . . ?
C6 O4 C7 61.68(7) . . ?
C2 C25 H27 109.5 . . ?
C2 C25 H28 109.5 . . ?
H27 C25 H28 109.5 . . ?
C2 C25 H29 109.5 . . ?
H27 C25 H29 109.5 . . ?
H28 C25 H29 109.5 . . ?
C16 O7 C17 116.94(10) . . ?
C18 O8 C19 115.23(9) . . ?
C23 O10 C24 118.17(10) . . ?
C3 N1 C12 117.77(9) . . ?
C3 N1 C4 122.16(9) . . ?
C12 N1 C4 119.71(9) . . ?
C2 C1 H5 109.5 . . ?
C2 C1 H4 109.5 . . ?
H5 C1 H4 109.5 . . ?
C2 C1 H1 109.5 . . ?
H5 C1 H1 109.5 . . ?
H4 C1 H1 109.5 . . ?
O1 C2 C25 102.09(9) . . ?
O1 C2 C11 111.02(10) . . ?
C25 C2 C11 111.09(11) . . ?
O1 C2 C1 109.41(10) . . ?
C25 C2 C1 110.45(12) . . ?
C11 C2 C1 112.31(11) . . ?
O6 C3 O1 124.50(10) . . ?
O6 C3 N1 123.94(11) . . ?
O1 C3 N1 111.56(9) . . ?
N1 C4 C21 111.71(9) . . ?
N1 C4 C5 112.09(8) . . ?
C21 C4 C5 108.55(9) . . ?
N1 C4 H20 108.1 . . ?
C21 C4 H20 108.1 . . ?
C5 C4 H20 108.1 . . ?
C6 C5 C4 108.19(8) . . ?
C6 C5 H21 110.1 . . ?
C4 C5 H21 110.1 . . ?
C6 C5 H22 110.1 . . ?
C4 C5 H22 110.1 . . ?
H21 C5 H22 108.4 . . ?
O4 C6 C7 59.45(7) . . ?
O4 C6 C22 110.89(9) . . ?
C7 C6 C22 117.95(9) . . ?
O4 C6 C5 118.75(9) . . ?
C7 C6 C5 117.25(9) . . ?
C22 C6 C5 118.66(9) . . ?
O4 C7 C6 58.87(7) . . ?
O4 C7 C20 115.14(9) . . ?
C6 C7 C20 117.05(9) . . ?
O4 C7 C8 114.79(9) . . ?
C6 C7 C8 116.30(9) . . ?
C20 C7 C8 119.90(9) . . ?
O3 C8 C9 121.04(10) . . ?
O3 C8 C7 122.33(10) . . ?
C9 C8 C7 116.54(9) . . ?
C23 C9 O2 121.15(11) . . ?
C23 C9 C8 119.35(10) . . ?
O2 C9 C8 118.42(10) . . ?
O2 C10 H2 109.5 . . ?
O2 C10 H26 109.5 . . ?
H2 C10 H26 109.5 . . ?
O2 C10 H3 109.5 . . ?
H2 C10 H3 109.5 . . ?
H26 C10 H3 109.5 . . ?
C2 C11 H6 109.5 . . ?
C2 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C2 C11 H8 109.5 . . ?
H6 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
N1 C12 C13 109.72(9) . . ?
N1 C12 H18 109.7 . . ?
C13 C12 H18 109.7 . . ?
N1 C12 H19 109.7 . . ?
C13 C12 H19 109.7 . . ?
H18 C12 H19 108.2 . . ?
C14 C13 C12 108.73(10) . . ?
C14 C13 H17 109.9 . . ?
C12 C13 H17 109.9 . . ?
C14 C13 H16 109.9 . . ?
C12 C13 H16 109.9 . . ?
H17 C13 H16 108.3 . . ?
C21 C14 C15 120.26(10) . . ?
C21 C14 C13 118.88(10) . . ?
C15 C14 C13 120.81(10) . . ?
C16 C15 C14 120.88(10) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O7 C16 C15 124.89(10) . . ?
O7 C16 C18 115.87(10) . . ?
C15 C16 C18 119.22(10) . . ?
O7 C17 H10 109.5 . . ?
O7 C17 H9 109.5 . . ?
H10 C17 H9 109.5 . . ?
O7 C17 H11 109.5 . . ?
H10 C17 H11 109.5 . . ?
H9 C17 H11 109.5 . . ?
O8 C18 C20 117.70(10) . . ?
O8 C18 C16 122.26(10) . . ?
C20 C18 C16 119.76(10) . . ?
O8 C19 H13 109.5 . . ?
O8 C19 H12 109.5 . . ?
H13 C19 H12 109.5 . . ?
O8 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
H12 C19 H14 109.5 . . ?
C18 C20 C21 121.04(10) . . ?
C18 C20 C7 119.47(9) . . ?
C21 C20 C7 119.35(9) . . ?
C14 C21 C20 118.79(10) . . ?
C14 C21 C4 123.67(9) . . ?
C20 C21 C4 117.48(9) . . ?
O9 C22 C23 121.44(11) . . ?
O9 C22 C6 120.88(10) . . ?
C23 C22 C6 117.58(10) . . ?
O10 C23 C9 126.71(11) . . ?
O10 C23 C22 112.33(10) . . ?
C9 C23 C22 120.95(10) . . ?
O10 C24 H25 109.5 . . ?
O10 C24 H24 109.5 . . ?
H25 C24 H24 109.5 . . ?
O10 C24 H23 109.5 . . ?
H25 C24 H23 109.5 . . ?
H24 C24 H23 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1SA O1SA H1SA 109.5 . . ?
O1SA C1SA H1S4 109.5 . . ?
O1SA C1SA H1S5 109.5 . . ?
H1S4 C1SA H1S5 109.5 . . ?
O1SA C1SA H1S6 109.5 . . ?
H1S4 C1SA H1S6 109.5 . . ?
H1S5 C1SA H1S6 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 C3 1.3454(14) . ?
O1 C2 1.4808(13) . ?
O2 C9 1.3567(14) . ?
O2 C10 1.4404(18) . ?
O3 C8 1.2177(13) . ?
O4 C6 1.4420(13) . ?
O4 C7 1.4508(13) . ?
C25 C2 1.5160(18) . ?
C25 H27 0.9800 . ?
C25 H28 0.9800 . ?
C25 H29 0.9800 . ?
O6 C3 1.2255(14) . ?
O7 C16 1.3643(13) . ?
O7 C17 1.4328(15) . ?
O8 C18 1.3778(13) . ?
O8 C19 1.4420(14) . ?
O9 C22 1.2095(14) . ?
O10 C23 1.3518(14) . ?
O10 C24 1.4330(15) . ?
N1 C3 1.3583(14) . ?
N1 C12 1.4624(15) . ?
N1 C4 1.4734(13) . ?
C1 C2 1.5213(18) . ?
C1 H5 0.9800 . ?
C1 H4 0.9800 . ?
C1 H1 0.9800 . ?
C2 C11 1.5200(18) . ?
C4 C21 1.5188(15) . ?
C4 C5 1.5469(15) . ?
C4 H20 1.0000 . ?
C5 C6 1.5156(15) . ?
C5 H21 0.9900 . ?
C5 H22 0.9900 . ?
C6 C7 1.4829(15) . ?
C6 C22 1.5125(15) . ?
C7 C20 1.4886(15) . ?
C7 C8 1.5013(15) . ?
C8 C9 1.4900(16) . ?
C9 C23 1.3520(16) . ?
C10 H2 0.9800 . ?
C10 H26 0.9800 . ?
C10 H3 0.9800 . ?
C11 H6 0.9800 . ?
C11 H7 0.9800 . ?
C11 H8 0.9800 . ?
C12 C13 1.5217(16) . ?
C12 H18 0.9900 . ?
C12 H19 0.9900 . ?
C13 C14 1.5011(15) . ?
C13 H17 0.9900 . ?
C13 H16 0.9900 . ?
C14 C21 1.3912(15) . ?
C14 C15 1.3985(15) . ?
C15 C16 1.3903(16) . ?
C15 H15 0.9500 . ?
C16 C18 1.4057(16) . ?
C17 H10 0.9800 . ?
C17 H9 0.9800 . ?
C17 H11 0.9800 . ?
C18 C20 1.3894(15) . ?
C19 H13 0.9800 . ?
C19 H12 0.9800 . ?
C19 H14 0.9800 . ?
C20 C21 1.4077(14) . ?
C22 C23 1.4930(16) . ?
C24 H25 0.9800 . ?
C24 H24 0.9800 . ?
C24 H23 0.9800 . ?
O1S C1S 1.415(4) . ?
O1S H1S 0.8400 . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1SA C1SA 1.413(3) . ?
O1SA H1SA 0.8400 . ?
C1SA H1S4 0.9800 . ?
C1SA H1S5 0.9800 . ?
C1SA H1S6 0.9800 . ?
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
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
C1 H5 O6 0.98 2.47 3.0084(16) 114.3 .
C5 H21 O1 0.99 2.47 3.0110(14) 113.7 .
C10 H2 O10 0.98 2.49 3.2668(17) 136.0 3_675
C10 H26 O1SA 0.98 2.64 3.555(3) 156.0 1_565
C11 H8 O6 0.98 2.41 2.9543(17) 114.4 .
C12 H19 O6 0.99 2.63 3.5940(16) 163.4 3_565
C19 H13 O7 0.98 2.36 2.8946(16) 113.7 .
C19 H14 O3 0.98 2.55 3.0738(16) 113.2 .
O1S H1S O6 0.84 1.89 2.721(2) 170.3 3_655
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
C3 O1 C2 C25 177.84(11) . . . . ?
C3 O1 C2 C11 -63.71(14) . . . . ?
C3 O1 C2 C1 60.81(14) . . . . ?
C2 O1 C3 O6 8.70(17) . . . . ?
C2 O1 C3 N1 -171.31(9) . . . . ?
C12 N1 C3 O6 0.36(16) . . . . ?
C4 N1 C3 O6 -172.82(10) . . . . ?
C12 N1 C3 O1 -179.63(10) . . . . ?
C4 N1 C3 O1 7.19(14) . . . . ?
C3 N1 C4 C21 -169.61(9) . . . . ?
C12 N1 C4 C21 17.34(13) . . . . ?
C3 N1 C4 C5 68.31(13) . . . . ?
C12 N1 C4 C5 -104.74(11) . . . . ?
N1 C4 C5 C6 -173.76(9) . . . . ?
C21 C4 C5 C6 62.38(11) . . . . ?
C7 O4 C6 C22 -110.94(10) . . . . ?
C7 O4 C6 C5 106.42(11) . . . . ?
C4 C5 C6 O4 -107.36(10) . . . . ?
C4 C5 C6 C7 -39.05(13) . . . . ?
C4 C5 C6 C22 112.88(10) . . . . ?
C6 O4 C7 C20 -107.66(10) . . . . ?
C6 O4 C7 C8 106.93(10) . . . . ?
C22 C6 C7 O4 98.95(10) . . . . ?
C5 C6 C7 O4 -108.92(10) . . . . ?
O4 C6 C7 C20 104.41(10) . . . . ?
C22 C6 C7 C20 -156.64(10) . . . . ?
C5 C6 C7 C20 -4.51(14) . . . . ?
O4 C6 C7 C8 -104.35(10) . . . . ?
C22 C6 C7 C8 -5.41(14) . . . . ?
C5 C6 C7 C8 146.73(10) . . . . ?
O4 C7 C8 O3 149.21(10) . . . . ?
C6 C7 C8 O3 -144.80(11) . . . . ?
C20 C7 C8 O3 5.57(16) . . . . ?
O4 C7 C8 C9 -34.29(13) . . . . ?
C6 C7 C8 C9 31.70(14) . . . . ?
C20 C7 C8 C9 -177.94(10) . . . . ?
C10 O2 C9 C23 147.40(12) . . . . ?
C10 O2 C9 C8 -44.57(16) . . . . ?
O3 C8 C9 C23 141.21(12) . . . . ?
C7 C8 C9 C23 -35.34(15) . . . . ?
O3 C8 C9 O2 -27.04(17) . . . . ?
C7 C8 C9 O2 156.41(10) . . . . ?
C3 N1 C12 C13 134.67(11) . . . . ?
C4 N1 C12 C13 -51.98(13) . . . . ?
N1 C12 C13 C14 58.74(13) . . . . ?
C12 C13 C14 C21 -35.90(14) . . . . ?
C12 C13 C14 C15 141.48(11) . . . . ?
C21 C14 C15 C16 0.22(17) . . . . ?
C13 C14 C15 C16 -177.12(11) . . . . ?
C17 O7 C16 C15 0.88(17) . . . . ?
C17 O7 C16 C18 179.17(11) . . . . ?
C14 C15 C16 O7 176.69(11) . . . . ?
C14 C15 C16 C18 -1.54(17) . . . . ?
C19 O8 C18 C20 -122.77(11) . . . . ?
C19 O8 C18 C16 63.37(14) . . . . ?
O7 C16 C18 O8 -3.75(16) . . . . ?
C15 C16 C18 O8 174.64(10) . . . . ?
O7 C16 C18 C20 -177.50(10) . . . . ?
C15 C16 C18 C20 0.90(17) . . . . ?
O8 C18 C20 C21 -172.96(10) . . . . ?
C16 C18 C20 C21 1.06(16) . . . . ?
O8 C18 C20 C7 2.62(15) . . . . ?
C16 C18 C20 C7 176.65(10) . . . . ?
O4 C7 C20 C18 -82.76(12) . . . . ?
C6 C7 C20 C18 -149.08(10) . . . . ?
C8 C7 C20 C18 60.76(14) . . . . ?
O4 C7 C20 C21 92.90(12) . . . . ?
C6 C7 C20 C21 26.58(14) . . . . ?
C8 C7 C20 C21 -123.58(11) . . . . ?
C15 C14 C21 C20 1.71(16) . . . . ?
C13 C14 C21 C20 179.11(10) . . . . ?
C15 C14 C21 C4 -175.39(10) . . . . ?
C13 C14 C21 C4 2.00(16) . . . . ?
C18 C20 C21 C14 -2.37(16) . . . . ?
C7 C20 C21 C14 -177.96(10) . . . . ?
C18 C20 C21 C4 174.92(10) . . . . ?
C7 C20 C21 C4 -0.67(14) . . . . ?
N1 C4 C21 C14 9.01(14) . . . . ?
C5 C4 C21 C14 133.10(11) . . . . ?
N1 C4 C21 C20 -168.13(9) . . . . ?
C5 C4 C21 C20 -44.04(12) . . . . ?
O4 C6 C22 O9 -129.17(12) . . . . ?
C7 C6 C22 O9 165.25(11) . . . . ?
C5 C6 C22 O9 13.51(16) . . . . ?
O4 C6 C22 C23 47.06(13) . . . . ?
C7 C6 C22 C23 -18.53(15) . . . . ?
C5 C6 C22 C23 -170.26(10) . . . . ?
C24 O10 C23 C9 35.55(19) . . . . ?
C24 O10 C23 C22 -143.12(12) . . . . ?
O2 C9 C23 O10 -0.1(2) . . . . ?
C8 C9 C23 O10 -168.05(11) . . . . ?
O2 C9 C23 C22 178.43(11) . . . . ?
C8 C9 C23 C22 10.52(17) . . . . ?
O9 C22 C23 O10 11.51(16) . . . . ?
C6 C22 C23 O10 -164.69(10) . . . . ?
O9 C22 C23 C9 -167.25(12) . . . . ?
C6 C22 C23 C9 16.55(16) . . . . ?
