#------------------------------------------------------------------------------
#$Date: 2020-10-22 02:23:33 +0300 (Thu, 22 Oct 2020) $
#$Revision: 258534 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038911.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_4038911
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         'C26 H31 N O10, C H2 Cl2'
_chemical_formula_sum            'C27 H33 Cl2 N O10'
_chemical_formula_weight         602.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.931(3)
_cell_angle_beta                 105.413(2)
_cell_angle_gamma                92.310(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0864(13)
_cell_length_b                   12.184(2)
_cell_length_c                   15.082(3)
_cell_measurement_reflns_used    7662
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.78
_cell_measurement_theta_min      2.56
_cell_volume                     1374.7(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.912
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18442
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.034
_diffrn_reflns_theta_min         1.458
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.510
_exptl_crystal_size_min          0.430
_exptl_transmission_factor_max   0.2134
_exptl_transmission_factor_min   0.1575
_refine_diff_density_max         2.311
_refine_diff_density_min         -2.675
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         8005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.1029
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1996P)²+3.3628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3081
_refine_ls_wR_factor_ref         0.3293
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6307
_reflns_number_total             8005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01900_si_002.cif
_cod_data_source_block           mo_zhb_zyj4_0m
_cod_database_code               4038911
_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   0.836
_shelx_estimated_absorpt_t_max   0.883
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.3987(3) 0.61512(19) 0.67288(16) 0.0173(4) Uani 1 1 d . . . . .
Cl1 Cl 0.9010(3) 1.01302(17) 0.09213(15) 0.0835(6) Uani 1 1 d . . . . .
O2 O 0.6659(3) 0.74955(19) 0.20582(16) 0.0182(4) Uani 1 1 d . . . . .
O3 O 0.2077(3) 0.6094(2) 0.53021(18) 0.0252(5) Uani 1 1 d . . . . .
O4 O 0.1149(3) 0.5195(2) 0.19009(17) 0.0239(5) Uani 1 1 d . . . . .
O5 O 0.0991(3) 0.67667(19) 0.08078(16) 0.0190(4) Uani 1 1 d . . . . .
O6 O 0.2713(3) 0.8670(2) 0.20043(18) 0.0216(5) Uani 1 1 d . . . . .
H10 H 0.320(7) 0.916(5) 0.211(4) 0.032 Uiso 1 1 d . U . . .
O7 O 0.5844(3) 0.97875(18) 0.31845(16) 0.0184(4) Uani 1 1 d . . . . .
O8 O 0.7945(3) 1.11302(18) 0.48912(17) 0.0214(5) Uani 1 1 d . . . . .
O9 O 0.5228(3) 0.8433(2) 0.10345(18) 0.0237(5) Uani 1 1 d . . . . .
Cl2 Cl 0.6763(3) 0.8648(2) -0.09259(16) 0.0860(6) Uani 1 1 d . . . . .
N1 N 0.4970(3) 0.6565(2) 0.55781(19) 0.0165(5) Uani 1 1 d . . . . .
C1 C 0.1739(5) 0.4599(3) 0.6519(3) 0.0242(6) Uani 1 1 d . . . . .
H30 H 0.1065 0.4645 0.5888 0.036 Uiso 1 1 calc R U . . .
H1 H 0.0967 0.4320 0.6837 0.036 Uiso 1 1 calc R U . . .
H29 H 0.2607 0.4071 0.6443 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2634(4) 0.5777(3) 0.7122(2) 0.0174(5) Uani 1 1 d . . . . .
C3 C 0.3536(4) 0.6253(3) 0.5832(2) 0.0175(5) Uani 1 1 d . . . . .
C4 C 0.4743(3) 0.6867(2) 0.4708(2) 0.0146(5) Uani 1 1 d . . . . .
C5 C 0.3635(4) 0.6204(2) 0.3866(2) 0.0165(5) Uani 1 1 d . . . . .
H6 H 0.3011 0.5514 0.3842 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3449(4) 0.6573(2) 0.3039(2) 0.0152(5) Uani 1 1 d . . . . .
C7 C 0.4303(3) 0.7578(2) 0.3026(2) 0.0134(5) Uani 1 1 d . . . . .
C8 C 0.3765(4) 0.7762(2) 0.2028(2) 0.0155(5) Uani 1 1 d . . . . .
C9 C 0.5301(4) 0.7944(2) 0.1644(2) 0.0160(5) Uani 1 1 d . . . . .
C10 C 0.8129(4) 0.7523(3) 0.1685(3) 0.0235(6) Uani 1 1 d . . . . .
H2 H 0.7725 0.7358 0.0986 0.035 Uiso 1 1 calc R U . . .
H19 H 0.8865 0.6947 0.1857 0.035 Uiso 1 1 calc R U . . .
H18 H 0.8793 0.8283 0.1958 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1381(4) 0.6678(3) 0.7221(3) 0.0246(6) Uani 1 1 d . . . . .
H32 H 0.2031 0.7422 0.7600 0.037 Uiso 1 1 calc R U . . .
H31 H 0.0566 0.6462 0.7543 0.037 Uiso 1 1 calc R U . . .
H3 H 0.0744 0.6726 0.6584 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6709(4) 0.6891(3) 0.6250(2) 0.0178(5) Uani 1 1 d . . . . .
H24 H 0.7562 0.6508 0.5951 0.021 Uiso 1 1 calc R U . . .
H25 H 0.6757 0.6648 0.6834 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7145(4) 0.8184(3) 0.6517(2) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.6419 0.8562 0.6913 0.023 Uiso 1 1 calc R U . . .
H4 H 0.8370 0.8399 0.6899 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6835(4) 0.8589(2) 0.5621(2) 0.0156(5) Uani 1 1 d . . . . .
C15 C 0.5697(3) 0.7908(2) 0.4745(2) 0.0137(5) Uani 1 1 d . . . . .
C16 C 0.2238(4) 0.6008(2) 0.2094(2) 0.0160(5) Uani 1 1 d . . . . .
C17 C 0.2574(4) 0.6624(2) 0.1373(2) 0.0153(5) Uani 1 1 d . . . . .
C18 C 0.1030(4) 0.7249(3) 0.0036(2) 0.0244(6) Uani 1 1 d . . . . .
H8 H 0.2210 0.7304 -0.0018 0.037 Uiso 1 1 calc R U . . .
H7 H 0.0652 0.8014 0.0166 0.037 Uiso 1 1 calc R U . . .
H9 H 0.0255 0.6758 -0.0565 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5438(3) 0.8298(2) 0.3898(2) 0.0135(5) Uani 1 1 d . . . . .
C20 C 0.6254(4) 0.9394(2) 0.3985(2) 0.0141(5) Uani 1 1 d . . . . .
C21 C 0.7162(5) 1.0389(3) 0.2958(3) 0.0282(7) Uani 1 1 d . . . . .
H13 H 0.7189 1.1213 0.3235 0.042 Uiso 1 1 calc R U . . .
H11 H 0.6915 1.0219 0.2262 0.042 Uiso 1 1 calc R U . . .
H12 H 0.8284 1.0147 0.3224 0.042 Uiso 1 1 calc R U . . .
C22 C 0.7307(4) 1.0060(2) 0.4864(2) 0.0154(5) Uani 1 1 d . . . . .
C23 C 0.9242(4) 1.1778(3) 0.5727(2) 0.0207(6) Uani 1 1 d . . . . .
H16 H 0.8791 1.1897 0.6283 0.031 Uiso 1 1 calc R U . . .
H15 H 0.9571 1.2520 0.5645 0.031 Uiso 1 1 calc R U . . .
H14 H 1.0257 1.1361 0.5829 0.031 Uiso 1 1 calc R U . . .
C24 C 0.7632(4) 0.9635(2) 0.5666(2) 0.0166(5) Uani 1 1 d . . . . .
H17 H 0.8416 1.0076 0.6253 0.020 Uiso 1 1 calc R U . . .
O10 O 0.3599(3) 0.59893(17) 0.08425(15) 0.0155(4) Uani 1 1 d . . . . .
C26 C 0.2786(4) 0.4879(3) 0.0235(2) 0.0182(5) Uani 1 1 d . . . . .
H21 H 0.2631 0.4382 0.0632 0.027 Uiso 1 1 calc R U . . .
H22 H 0.3516 0.4544 -0.0164 0.027 Uiso 1 1 calc R U . . .
H23 H 0.1658 0.4955 -0.0176 0.027 Uiso 1 1 calc R U . . .
C25 C 0.3671(5) 0.5721(3) 0.8108(2) 0.0251(6) Uani 1 1 d . . . . .
H27 H 0.4486 0.5153 0.8038 0.038 Uiso 1 1 calc R U . . .
H26 H 0.2886 0.5501 0.8444 0.038 Uiso 1 1 calc R U . . .
H28 H 0.4310 0.6472 0.8475 0.038 Uiso 1 1 calc R U . . .
C27 C 0.7049(13) 0.9892(7) 0.0046(7) 0.085(2) Uani 1 1 d . . . . .
H27A H 0.6919 1.0565 -0.0210 0.102 Uiso 1 1 calc R U . . .
H27B H 0.6114 0.9839 0.0349 0.102 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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 119.3(2) . . ?
C9 O2 C10 116.1(2) . . ?
C17 O5 C18 116.1(2) . . ?
C8 O6 H10 110(5) . . ?
C20 O7 C21 119.9(3) . . ?
C22 O8 C23 118.6(3) . . ?
C3 N1 C4 119.5(2) . . ?
C3 N1 C12 123.6(3) . . ?
C4 N1 C12 115.1(2) . . ?
C2 C1 H30 109.5 . . ?
C2 C1 H1 109.5 . . ?
H30 C1 H1 109.5 . . ?
C2 C1 H29 109.5 . . ?
H30 C1 H29 109.5 . . ?
H1 C1 H29 109.5 . . ?
O1 C2 C1 110.6(2) . . ?
O1 C2 C25 102.6(2) . . ?
C1 C2 C25 110.1(3) . . ?
O1 C2 C11 110.1(2) . . ?
C1 C2 C11 113.0(3) . . ?
C25 C2 C11 110.0(3) . . ?
O3 C3 O1 125.5(3) . . ?
O3 C3 N1 123.4(3) . . ?
O1 C3 N1 111.0(2) . . ?
C5 C4 N1 121.4(2) . . ?
C5 C4 C15 121.0(3) . . ?
N1 C4 C15 117.6(2) . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H6 121.0 . . ?
C6 C5 H6 121.0 . . ?
C7 C6 C5 124.0(3) . . ?
C7 C6 C16 110.7(3) . . ?
C5 C6 C16 125.2(3) . . ?
C6 C7 C19 119.1(3) . . ?
C6 C7 C8 111.3(2) . . ?
C19 C7 C8 129.5(2) . . ?
O6 C8 C7 111.1(2) . . ?
O6 C8 C9 111.2(2) . . ?
C7 C8 C9 113.2(2) . . ?
O6 C8 C17 106.7(2) . . ?
C7 C8 C17 104.3(2) . . ?
C9 C8 C17 109.9(2) . . ?
O9 C9 O2 125.9(3) . . ?
O9 C9 C8 122.6(3) . . ?
O2 C9 C8 111.4(2) . . ?
O2 C10 H2 109.5 . . ?
O2 C10 H19 109.5 . . ?
H2 C10 H19 109.5 . . ?
O2 C10 H18 109.5 . . ?
H2 C10 H18 109.5 . . ?
H19 C10 H18 109.5 . . ?
C2 C11 H32 109.5 . . ?
C2 C11 H31 109.5 . . ?
H32 C11 H31 109.5 . . ?
C2 C11 H3 109.5 . . ?
H32 C11 H3 109.5 . . ?
H31 C11 H3 109.5 . . ?
N1 C12 C13 109.2(2) . . ?
N1 C12 H24 109.8 . . ?
C13 C12 H24 109.8 . . ?
N1 C12 H25 109.8 . . ?
C13 C12 H25 109.8 . . ?
H24 C12 H25 108.3 . . ?
C14 C13 C12 110.4(2) . . ?
C14 C13 H5 109.6 . . ?
C12 C13 H5 109.6 . . ?
C14 C13 H4 109.6 . . ?
C12 C13 H4 109.6 . . ?
H5 C13 H4 108.1 . . ?
C24 C14 C15 120.0(3) . . ?
C24 C14 C13 119.9(3) . . ?
C15 C14 C13 120.0(2) . . ?
C14 C15 C4 120.5(3) . . ?
C14 C15 C19 119.3(2) . . ?
C4 C15 C19 120.2(3) . . ?
O4 C16 C6 126.7(3) . . ?
O4 C16 C17 125.1(3) . . ?
C6 C16 C17 108.2(2) . . ?
O5 C17 O10 113.4(2) . . ?
O5 C17 C16 107.8(2) . . ?
O10 C17 C16 109.6(2) . . ?
O5 C17 C8 115.9(2) . . ?
O10 C17 C8 105.8(2) . . ?
C16 C17 C8 103.9(2) . . ?
O5 C18 H8 109.5 . . ?
O5 C18 H7 109.5 . . ?
H8 C18 H7 109.5 . . ?
O5 C18 H9 109.5 . . ?
H8 C18 H9 109.5 . . ?
H7 C18 H9 109.5 . . ?
C20 C19 C7 123.8(3) . . ?
C20 C19 C15 118.6(3) . . ?
C7 C19 C15 117.5(2) . . ?
O7 C20 C22 122.2(2) . . ?
O7 C20 C19 117.0(2) . . ?
C22 C20 C19 120.6(3) . . ?
O7 C21 H13 109.5 . . ?
O7 C21 H11 109.5 . . ?
H13 C21 H11 109.5 . . ?
O7 C21 H12 109.5 . . ?
H13 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
O8 C22 C20 116.4(3) . . ?
O8 C22 C24 123.6(3) . . ?
C20 C22 C24 120.0(3) . . ?
O8 C23 H16 109.5 . . ?
O8 C23 H15 109.5 . . ?
H16 C23 H15 109.5 . . ?
O8 C23 H14 109.5 . . ?
H16 C23 H14 109.5 . . ?
H15 C23 H14 109.5 . . ?
C14 C24 C22 121.4(3) . . ?
C14 C24 H17 119.3 . . ?
C22 C24 H17 119.3 . . ?
C17 O10 C26 114.9(2) . . ?
O10 C26 H21 109.5 . . ?
O10 C26 H22 109.5 . . ?
H21 C26 H22 109.5 . . ?
O10 C26 H23 109.5 . . ?
H21 C26 H23 109.5 . . ?
H22 C26 H23 109.5 . . ?
C2 C25 H27 109.5 . . ?
C2 C25 H26 109.5 . . ?
H27 C25 H26 109.5 . . ?
C2 C25 H28 109.5 . . ?
H27 C25 H28 109.5 . . ?
H26 C25 H28 109.5 . . ?
Cl1 C27 Cl2 115.4(5) . . ?
Cl1 C27 H27A 108.4 . . ?
Cl2 C27 H27A 108.4 . . ?
Cl1 C27 H27B 108.4 . . ?
Cl2 C27 H27B 108.4 . . ?
H27A C27 H27B 107.5 . . ?
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 1.343(4) . ?
O1 C2 1.484(3) . ?
Cl1 C27 1.730(10) . ?
O2 C9 1.325(4) . ?
O2 C10 1.447(4) . ?
O3 C3 1.212(4) . ?
O4 C16 1.219(4) . ?
O5 C17 1.382(3) . ?
O5 C18 1.439(4) . ?
O6 C8 1.425(3) . ?
O6 H10 0.66(6) . ?
O7 C20 1.377(4) . ?
O7 C21 1.431(4) . ?
O8 C22 1.369(3) . ?
O8 C23 1.425(4) . ?
O9 C9 1.207(4) . ?
Cl2 C27 1.774(10) . ?
N1 C3 1.383(4) . ?
N1 C4 1.420(4) . ?
N1 C12 1.467(4) . ?
C1 C2 1.518(4) . ?
C1 H30 0.9800 . ?
C1 H1 0.9800 . ?
C1 H29 0.9800 . ?
C2 C25 1.520(4) . ?
C2 C11 1.529(4) . ?
C4 C5 1.370(4) . ?
C4 C15 1.439(4) . ?
C5 C6 1.406(4) . ?
C5 H6 0.9500 . ?
C6 C7 1.388(4) . ?
C6 C16 1.470(4) . ?
C7 C19 1.428(4) . ?
C7 C8 1.529(4) . ?
C8 C9 1.534(4) . ?
C8 C17 1.583(4) . ?
C10 H2 0.9800 . ?
C10 H19 0.9800 . ?
C10 H18 0.9800 . ?
C11 H32 0.9800 . ?
C11 H31 0.9800 . ?
C11 H3 0.9800 . ?
C12 C13 1.523(4) . ?
C12 H24 0.9900 . ?
C12 H25 0.9900 . ?
C13 C14 1.518(4) . ?
C13 H5 0.9900 . ?
C13 H4 0.9900 . ?
C14 C24 1.382(4) . ?
C14 C15 1.417(4) . ?
C15 C19 1.442(4) . ?
C16 C17 1.543(4) . ?
C17 O10 1.417(3) . ?
C18 H8 0.9800 . ?
C18 H7 0.9800 . ?
C18 H9 0.9800 . ?
C19 C20 1.424(4) . ?
C20 C22 1.390(4) . ?
C21 H13 0.9800 . ?
C21 H11 0.9800 . ?
C21 H12 0.9800 . ?
C22 C24 1.402(4) . ?
C23 H16 0.9800 . ?
C23 H15 0.9800 . ?
C23 H14 0.9800 . ?
C24 H17 0.9500 . ?
O10 C26 1.439(3) . ?
C26 H21 0.9800 . ?
C26 H22 0.9800 . ?
C26 H23 0.9800 . ?
C25 H27 0.9800 . ?
C25 H26 0.9800 . ?
C25 H28 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
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
C27 H27B O9 0.99 2.39 3.143(8) 132.0 .
C27 H27A O9 0.99 2.42 3.261(8) 142.3 2_675
C26 H21 O4 0.98 2.53 3.086(4) 115.6 .
C21 H11 O9 0.98 2.52 3.205(4) 126.6 .
C21 H11 Cl1 0.98 2.95 3.708(4) 135.2 .
C18 H8 O9 0.98 2.63 3.412(4) 137.0 .
C11 H3 O3 0.98 2.43 3.006(4) 117.2 .
C1 H30 O3 0.98 2.65 3.445(4) 137.9 2_566
C1 H30 O3 0.98 2.37 2.951(4) 117.0 .
O6 H10 O7 0.66(6) 2.27(6) 2.741(3) 130(6) .
C27 H27B O9 0.99 2.39 3.143(8) 132.0 .
C27 H27A O9 0.99 2.42 3.261(8) 142.3 2_675
C26 H21 O4 0.98 2.53 3.086(4) 115.6 .
C21 H11 O9 0.98 2.52 3.205(4) 126.6 .
C21 H11 Cl1 0.98 2.95 3.708(4) 135.2 .
C18 H8 O9 0.98 2.63 3.412(4) 137.0 .
C11 H3 O3 0.98 2.43 3.006(4) 117.2 .
C1 H30 O3 0.98 2.37 2.951(4) 117.0 .
O6 H10 O7 0.66(6) 2.27(6) 2.741(3) 130(6) .
C1 H30 O3 0.98 2.37 2.951(4) 117.0 .
C1 H30 O3 0.98 2.65 3.445(4) 137.9 2_566
C11 H3 O3 0.98 2.43 3.006(4) 117.2 .
C18 H8 O9 0.98 2.63 3.412(4) 137.0 .
C21 H11 Cl1 0.98 2.95 3.708(4) 135.2 .
C21 H11 O9 0.98 2.52 3.205(4) 126.6 .
C26 H21 O4 0.98 2.53 3.086(4) 115.6 .
C27 H27A O9 0.99 2.42 3.261(8) 142.3 2_675
C27 H27B O9 0.99 2.39 3.143(8) 132.0 .
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 C1 60.1(3) . . . . ?
C3 O1 C2 C25 177.4(3) . . . . ?
C3 O1 C2 C11 -65.5(3) . . . . ?
C2 O1 C3 O3 2.2(5) . . . . ?
C2 O1 C3 N1 -177.6(2) . . . . ?
C4 N1 C3 O3 8.7(5) . . . . ?
C12 N1 C3 O3 172.4(3) . . . . ?
C4 N1 C3 O1 -171.4(2) . . . . ?
C12 N1 C3 O1 -7.7(4) . . . . ?
C3 N1 C4 C5 -47.7(4) . . . . ?
C12 N1 C4 C5 147.3(3) . . . . ?
C3 N1 C4 C15 131.3(3) . . . . ?
C12 N1 C4 C15 -33.8(3) . . . . ?
N1 C4 C5 C6 178.5(2) . . . . ?
C15 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 C6 C16 -175.8(3) . . . . ?
C5 C6 C7 C19 -0.4(4) . . . . ?
C16 C6 C7 C19 175.2(2) . . . . ?
C5 C6 C7 C8 -177.5(3) . . . . ?
C16 C6 C7 C8 -2.0(3) . . . . ?
C6 C7 C8 O6 108.3(3) . . . . ?
C19 C7 C8 O6 -68.5(4) . . . . ?
C6 C7 C8 C9 -125.8(3) . . . . ?
C19 C7 C8 C9 57.5(4) . . . . ?
C6 C7 C8 C17 -6.3(3) . . . . ?
C19 C7 C8 C17 177.0(3) . . . . ?
C10 O2 C9 O9 -5.1(4) . . . . ?
C10 O2 C9 C8 174.4(2) . . . . ?
O6 C8 C9 O9 -31.0(4) . . . . ?
C7 C8 C9 O9 -156.9(3) . . . . ?
C17 C8 C9 O9 86.9(3) . . . . ?
O6 C8 C9 O2 149.5(2) . . . . ?
C7 C8 C9 O2 23.6(3) . . . . ?
C17 C8 C9 O2 -92.6(3) . . . . ?
C3 N1 C12 C13 -104.7(3) . . . . ?
C4 N1 C12 C13 59.7(3) . . . . ?
N1 C12 C13 C14 -51.6(3) . . . . ?
C12 C13 C14 C24 -159.6(3) . . . . ?
C12 C13 C14 C15 22.1(4) . . . . ?
C24 C14 C15 C4 -174.4(3) . . . . ?
C13 C14 C15 C4 3.9(4) . . . . ?
C24 C14 C15 C19 2.6(4) . . . . ?
C13 C14 C15 C19 -179.1(2) . . . . ?
C5 C4 C15 C14 179.9(3) . . . . ?
N1 C4 C15 C14 0.9(4) . . . . ?
C5 C4 C15 C19 2.9(4) . . . . ?
N1 C4 C15 C19 -176.1(2) . . . . ?
C7 C6 C16 O4 -170.2(3) . . . . ?
C5 C6 C16 O4 5.3(5) . . . . ?
C7 C6 C16 C17 9.8(3) . . . . ?
C5 C6 C16 C17 -174.7(3) . . . . ?
C18 O5 C17 O10 -53.8(3) . . . . ?
C18 O5 C17 C16 -175.3(2) . . . . ?
C18 O5 C17 C8 68.9(3) . . . . ?
O4 C16 C17 O5 43.6(4) . . . . ?
C6 C16 C17 O5 -136.4(2) . . . . ?
O4 C16 C17 O10 -80.3(3) . . . . ?
C6 C16 C17 O10 99.7(3) . . . . ?
O4 C16 C17 C8 167.0(3) . . . . ?
C6 C16 C17 C8 -13.0(3) . . . . ?
O6 C8 C17 O5 11.7(3) . . . . ?
C7 C8 C17 O5 129.4(2) . . . . ?
C9 C8 C17 O5 -108.9(3) . . . . ?
O6 C8 C17 O10 138.3(2) . . . . ?
C7 C8 C17 O10 -104.0(2) . . . . ?
C9 C8 C17 O10 17.7(3) . . . . ?
O6 C8 C17 C16 -106.3(2) . . . . ?
C7 C8 C17 C16 11.4(3) . . . . ?
C9 C8 C17 C16 133.1(2) . . . . ?
C6 C7 C19 C20 -174.0(2) . . . . ?
C8 C7 C19 C20 2.5(4) . . . . ?
C6 C7 C19 C15 2.8(4) . . . . ?
C8 C7 C19 C15 179.3(3) . . . . ?
C14 C15 C19 C20 -4.0(4) . . . . ?
C4 C15 C19 C20 173.0(2) . . . . ?
C14 C15 C19 C7 179.0(2) . . . . ?
C4 C15 C19 C7 -4.0(4) . . . . ?
C21 O7 C20 C22 44.5(4) . . . . ?
C21 O7 C20 C19 -140.5(3) . . . . ?
C7 C19 C20 O7 3.1(4) . . . . ?
C15 C19 C20 O7 -173.7(2) . . . . ?
C7 C19 C20 C22 178.2(2) . . . . ?
C15 C19 C20 C22 1.4(4) . . . . ?
C23 O8 C22 C20 -170.1(3) . . . . ?
C23 O8 C22 C24 11.3(4) . . . . ?
O7 C20 C22 O8 -1.1(4) . . . . ?
C19 C20 C22 O8 -175.9(2) . . . . ?
O7 C20 C22 C24 177.5(3) . . . . ?
C19 C20 C22 C24 2.7(4) . . . . ?
C15 C14 C24 C22 1.6(4) . . . . ?
C13 C14 C24 C22 -176.8(3) . . . . ?
O8 C22 C24 C14 174.2(3) . . . . ?
C20 C22 C24 C14 -4.3(4) . . . . ?
O5 C17 O10 C26 -55.5(3) . . . . ?
C16 C17 O10 C26 65.0(3) . . . . ?
C8 C17 O10 C26 176.5(2) . . . . ?
