#------------------------------------------------------------------------------
#$Date: 2021-07-03 02:14:58 +0300 (Sat, 03 Jul 2021) $
#$Revision: 266918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563902.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_1563902
loop_
_publ_author_name
'Chen, Jian-Jun'
'Bai, Wei'
'Lu, Yu-Bo'
'Feng, Zi-Yun'
'Gao, Kun'
'Yue, Jian-Min'
_publ_section_title
;
 Quassinoids with Inhibitory Activities against Plant Fungal Pathogens
 from Picrasma javanica.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00096
_journal_year                    2021
_chemical_absolute_configuration none
_chemical_formula_moiety         'C23 H32 O8, 2(C H Cl3)'
_chemical_formula_sum            'C25 H34 Cl6 O8'
_chemical_formula_weight         675.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3919(5)
_cell_length_b                   12.9423(6)
_cell_length_c                   21.1734(12)
_cell_measurement_reflns_used    3005
_cell_measurement_temperature    280(2)
_cell_measurement_theta_max      70.5120
_cell_measurement_theta_min      3.8490
_cell_volume                     3121.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      280(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0609844000
_diffrn_orient_matrix_UB_12      -0.0223429000
_diffrn_orient_matrix_UB_13      0.0634319000
_diffrn_orient_matrix_UB_21      -0.0622905000
_diffrn_orient_matrix_UB_22      -0.0939256000
_diffrn_orient_matrix_UB_23      -0.0296584000
_diffrn_orient_matrix_UB_31      0.1034262000
_diffrn_orient_matrix_UB_32      -0.0696984000
_diffrn_orient_matrix_UB_33      0.0196133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10501
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.806
_diffrn_reflns_theta_min         4.003
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.005(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5345
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0993P)²+0.5231P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.592
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                4720
_reflns_number_total             5345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00096_si_003.cif
_cod_data_source_block           chenjj_0113
_cod_original_cell_volume        3121.7(3)
_cod_database_code               1563902
_shelxl_version_number           2013-2
_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.
;
_reflns_odcompleteness_completeness 93.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl5) \\sim Ueq, Uanis(Cl5') \\sim Ueq, Uanis(Cl6) \\sim Ueq, Uanis(Cl6')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H25(0.5) H25A(0.5) Cl5(0.5) Cl6(0.5) Cl5'(0.5) Cl6'(0.5)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C14(H14), C25(H25),
 C25(H25A), C24(H24)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C15(H15A,H15B)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0843(2) -0.8491(2) 0.04405(16) 0.0522(7) Uani 1 1 d . . . . .
O2 O -0.0266(3) -0.9323(3) -0.06750(17) 0.0626(8) Uani 1 1 d . . . . .
O3 O 0.0369(3) -0.8998(2) 0.15440(16) 0.0543(7) Uani 1 1 d . . . . .
H3 H -0.0291 -0.9078 0.1397 0.081 Uiso 1 1 calc GR . . . .
O4 O -0.1304(3) -0.8179(3) 0.22887(17) 0.0627(9) Uani 1 1 d . . . . .
O5 O 0.0759(4) -0.8192(3) 0.32499(19) 0.0767(11) Uani 1 1 d . . . . .
O6 O 0.0905(3) -0.6582(2) 0.28832(14) 0.0564(8) Uani 1 1 d . . . . .
O7 O -0.2488(3) -0.4746(3) 0.10061(19) 0.0635(9) Uani 1 1 d . . . . .
O8 O -0.0649(3) -0.5041(2) 0.07860(14) 0.0490(7) Uani 1 1 d . . . . .
C1 C 0.0119(3) -0.8251(3) 0.02500(19) 0.0398(8) Uani 1 1 d . . . . .
C2 C 0.0546(4) -0.8636(3) -0.0392(2) 0.0482(9) Uani 1 1 d . . . . .
H2 H 0.1309 -0.8977 -0.0345 0.058 Uiso 1 1 calc R . . . .
C3 C 0.0664(4) -0.7712(4) -0.0834(2) 0.0516(10) Uani 1 1 d . . . . .
H3A H -0.0115 -0.7489 -0.0959 0.062 Uiso 1 1 calc R . . . .
H3B H 0.1072 -0.7933 -0.1213 0.062 Uiso 1 1 calc R . . . .
C4 C 0.1323(4) -0.6780(4) -0.05512(19) 0.0474(9) Uani 1 1 d . . . . .
H4 H 0.2143 -0.6981 -0.0482 0.057 Uiso 1 1 calc R . . . .
C5 C 0.0769(3) -0.6511(3) 0.00975(17) 0.0397(8) Uani 1 1 d . . . . .
H5 H -0.0074 -0.6424 0.0021 0.048 Uiso 1 1 calc R . . . .
C6 C 0.1197(4) -0.5489(3) 0.0381(2) 0.0462(9) Uani 1 1 d . . . . .
H6A H 0.2033 -0.5537 0.0465 0.055 Uiso 1 1 calc R . . . .
H6B H 0.1076 -0.4938 0.0077 0.055 Uiso 1 1 calc R . . . .
C7 C 0.0560(4) -0.5225(3) 0.0988(2) 0.0441(8) Uani 1 1 d . . . . .
H7 H 0.0882 -0.4579 0.1156 0.053 Uiso 1 1 calc R . . . .
C8 C 0.0681(3) -0.6067(3) 0.14959(18) 0.0389(8) Uani 1 1 d . . . . .
C9 C 0.0344(3) -0.7136(3) 0.12173(17) 0.0355(7) Uani 1 1 d . . . . .
H9 H -0.0503 -0.7099 0.1141 0.043 Uiso 1 1 calc R . . . .
C10 C 0.0888(3) -0.7429(3) 0.05732(18) 0.0376(7) Uani 1 1 d . . . . .
C11 C 0.0500(4) -0.7970(3) 0.17461(19) 0.0423(8) Uani 1 1 d . . . . .
H11 H 0.1283 -0.7891 0.1931 0.051 Uiso 1 1 calc R . . . .
C12 C -0.0403(4) -0.7691(3) 0.22402(19) 0.0449(9) Uani 1 1 d . . . . .
C13 C -0.0237(4) -0.6643(3) 0.2570(2) 0.0492(9) Uani 1 1 d . . . . .
C14 C -0.0179(4) -0.5802(3) 0.2044(2) 0.0442(8) Uani 1 1 d . . . . .
H14 H 0.0103 -0.5164 0.2242 0.053 Uiso 1 1 calc R . . . .
C15 C -0.1422(4) -0.5595(3) 0.1807(2) 0.0511(10) Uani 1 1 d . . . . .
H15A H -0.1832 -0.6252 0.1787 0.061 Uiso 1 1 calc R . . . .
H15B H -0.1820 -0.5175 0.2120 0.061 Uiso 1 1 calc R . . . .
C16 C -0.1554(4) -0.5080(3) 0.1184(2) 0.0475(9) Uani 1 1 d . . . . .
C17 C 0.1302(6) -0.5887(5) -0.1018(2) 0.0672(13) Uani 1 1 d . . . . .
H17A H 0.0512 -0.5641 -0.1064 0.101 Uiso 1 1 calc GR . . . .
H17B H 0.1590 -0.6119 -0.1420 0.101 Uiso 1 1 calc GR . . . .
H17C H 0.1791 -0.5338 -0.0864 0.101 Uiso 1 1 calc GR . . . .
C18 C 0.2174(3) -0.7798(4) 0.0643(2) 0.0493(10) Uani 1 1 d . . . . .
H18A H 0.2441 -0.8078 0.0248 0.074 Uiso 1 1 calc GR . . . .
H18B H 0.2217 -0.8322 0.0963 0.074 Uiso 1 1 calc GR . . . .
H18C H 0.2662 -0.7224 0.0760 0.074 Uiso 1 1 calc GR . . . .
C19 C 0.1968(4) -0.5951(4) 0.1727(2) 0.0511(10) Uani 1 1 d . . . . .
H19A H 0.2164 -0.6520 0.1998 0.077 Uiso 1 1 calc GR . . . .
H19B H 0.2050 -0.5315 0.1956 0.077 Uiso 1 1 calc GR . . . .
H19C H 0.2487 -0.5946 0.1370 0.077 Uiso 1 1 calc GR . . . .
C20 C -0.1183(6) -0.6445(4) 0.3062(2) 0.0687(14) Uani 1 1 d . . . . .
H20A H -0.1104 -0.6934 0.3400 0.103 Uiso 1 1 calc GR . . . .
H20B H -0.1942 -0.6519 0.2871 0.103 Uiso 1 1 calc GR . . . .
H20C H -0.1099 -0.5757 0.3225 0.103 Uiso 1 1 calc GR . . . .
C21 C -0.0254(5) -1.0316(4) -0.0398(3) 0.0746(15) Uani 1 1 d . . . . .
H21A H -0.0939 -1.0692 -0.0530 0.112 Uiso 1 1 calc GR . . . .
H21B H -0.0255 -1.0251 0.0053 0.112 Uiso 1 1 calc GR . . . .
H21C H 0.0437 -1.0680 -0.0530 0.112 Uiso 1 1 calc GR . . . .
C22 C 0.2363(7) -0.7116(6) 0.3584(3) 0.097(2) Uani 1 1 d . . . . .
H22A H 0.2844 -0.6681 0.3323 0.146 Uiso 1 1 calc GR . . . .
H22B H 0.2782 -0.7739 0.3682 0.146 Uiso 1 1 calc GR . . . .
H22C H 0.2173 -0.6759 0.3967 0.146 Uiso 1 1 calc GR . . . .
C23 C 0.1255(6) -0.7380(4) 0.3238(2) 0.0636(13) Uani 1 1 d . . . . .
Cl4 Cl -0.26559(17) -0.24726(15) -0.03943(10) 0.0945(5) Uani 1 1 d . . . . .
C25 C -0.1638(5) -0.3465(5) -0.0282(3) 0.0731(15) Uani 1 1 d . . . . .
H25 H -0.1582 -0.3632 0.0168 0.088 Uiso 0.5 1 calc R . P A 1
H25A H -0.1918 -0.3875 0.0077 0.088 Uiso 0.5 1 calc R . P A 2
Cl5 Cl -0.2102(7) -0.4564(4) -0.0707(3) 0.109(2) Uani 0.5 1 d . U P B 1
Cl6 Cl -0.0228(5) -0.3147(5) -0.0580(5) 0.150(3) Uani 0.5 1 d . U P B 1
Cl5' Cl -0.1555(8) -0.4266(7) -0.0896(4) 0.157(4) Uani 0.5 1 d . U P B 2
Cl6' Cl -0.0337(4) -0.2876(4) -0.0042(3) 0.119(2) Uani 0.5 1 d . U P B 2
Cl1 Cl -0.0096(3) -0.4320(2) -0.25511(12) 0.1179(7) Uani 1 1 d . . . . .
Cl2 Cl -0.13765(17) -0.6163(2) -0.22864(11) 0.1150(8) Uani 1 1 d . . . . .
Cl3 Cl 0.0877(2) -0.6263(2) -0.29051(12) 0.1151(7) Uani 1 1 d . . . . .
C24 C -0.0416(6) -0.5545(6) -0.2820(3) 0.0802(17) Uani 1 1 d . . . . .
H24 H -0.0802 -0.5491 -0.3232 0.096 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 '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
C21 O2 C2 113.0(4) . . ?
C11 O3 H3 109.5 . . ?
C23 O6 C13 118.6(4) . . ?
C16 O8 C7 122.5(3) . . ?
O1 C1 C2 120.2(4) . . ?
O1 C1 C10 123.1(4) . . ?
C2 C1 C10 116.1(3) . . ?
O2 C2 C1 111.9(3) . . ?
O2 C2 H2 109.8 . . ?
O2 C2 C3 106.9(4) . . ?
C1 C2 H2 109.8 . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 H2 109.8 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C2 C3 C4 114.7(3) . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C3 C4 H4 108.3 . . ?
C3 C4 C5 108.8(3) . . ?
C5 C4 H4 108.3 . . ?
C17 C4 C3 109.5(4) . . ?
C17 C4 H4 108.3 . . ?
C17 C4 C5 113.5(4) . . ?
C4 C5 H5 106.2 . . ?
C4 C5 C10 111.3(3) . . ?
C6 C5 C4 114.3(3) . . ?
C6 C5 H5 106.2 . . ?
C6 C5 C10 112.1(3) . . ?
C10 C5 H5 106.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.0(3) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
O8 C7 C6 103.8(3) . . ?
O8 C7 H7 108.6 . . ?
O8 C7 C8 113.9(3) . . ?
C6 C7 H7 108.6 . . ?
C6 C7 C8 113.0(3) . . ?
C8 C7 H7 108.6 . . ?
C7 C8 C9 110.1(3) . . ?
C7 C8 C14 108.0(3) . . ?
C7 C8 C19 103.7(3) . . ?
C9 C8 C14 108.9(3) . . ?
C9 C8 C19 116.0(3) . . ?
C19 C8 C14 109.7(3) . . ?
C8 C9 H9 105.2 . . ?
C8 C9 C11 108.4(3) . . ?
C10 C9 C8 117.1(3) . . ?
C10 C9 H9 105.2 . . ?
C10 C9 C11 114.6(3) . . ?
C11 C9 H9 105.2 . . ?
C1 C10 C5 100.9(3) . . ?
C1 C10 C9 109.5(3) . . ?
C1 C10 C18 111.6(3) . . ?
C9 C10 C5 110.3(3) . . ?
C9 C10 C18 111.8(3) . . ?
C18 C10 C5 112.2(3) . . ?
O3 C11 C9 115.0(3) . . ?
O3 C11 H11 108.5 . . ?
O3 C11 C12 111.4(3) . . ?
C9 C11 H11 108.5 . . ?
C12 C11 C9 104.7(3) . . ?
C12 C11 H11 108.5 . . ?
O4 C12 C11 120.8(4) . . ?
O4 C12 C13 121.8(4) . . ?
C11 C12 C13 116.2(3) . . ?
O6 C13 C12 111.3(4) . . ?
O6 C13 C14 104.4(3) . . ?
O6 C13 C20 108.1(4) . . ?
C12 C13 C14 107.3(3) . . ?
C20 C13 C12 111.9(4) . . ?
C20 C13 C14 113.6(4) . . ?
C8 C14 C13 113.9(3) . . ?
C8 C14 H14 107.3 . . ?
C13 C14 H14 107.3 . . ?
C15 C14 C8 112.1(3) . . ?
C15 C14 C13 108.6(3) . . ?
C15 C14 H14 107.3 . . ?
C14 C15 H15A 107.9 . . ?
C14 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C16 C15 C14 117.7(4) . . ?
C16 C15 H15A 107.9 . . ?
C16 C15 H15B 107.9 . . ?
O7 C16 O8 118.1(4) . . ?
O7 C16 C15 121.7(4) . . ?
O8 C16 C15 120.0(4) . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
O5 C23 O6 123.4(5) . . ?
O5 C23 C22 126.1(5) . . ?
O6 C23 C22 110.4(5) . . ?
Cl4 C25 H25 109.7 . . ?
Cl4 C25 H25A 106.7 . . ?
Cl4 C25 Cl5 109.0(4) . . ?
Cl4 C25 Cl6 112.5(4) . . ?
Cl5 C25 H25 109.7 . . ?
Cl5 C25 Cl6 106.1(5) . . ?
Cl6 C25 H25 109.7 . . ?
Cl5' C25 Cl4 112.9(4) . . ?
Cl5' C25 H25A 106.7 . . ?
Cl5' C25 Cl6' 116.8(6) . . ?
Cl6' C25 Cl4 106.4(4) . . ?
Cl6' C25 H25A 106.7 . . ?
Cl1 C24 Cl2 109.7(4) . . ?
Cl1 C24 Cl3 110.1(4) . . ?
Cl1 C24 H24 108.9 . . ?
Cl2 C24 H24 108.9 . . ?
Cl3 C24 Cl2 110.3(4) . . ?
Cl3 C24 H24 108.9 . . ?
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 C1 1.208(5) . ?
O2 C2 1.416(5) . ?
O2 C21 1.413(7) . ?
O3 H3 0.8200 . ?
O3 C11 1.405(5) . ?
O4 C12 1.209(5) . ?
O5 C23 1.193(6) . ?
O6 C13 1.461(6) . ?
O6 C23 1.338(6) . ?
O7 C16 1.208(6) . ?
O8 C7 1.462(5) . ?
O8 C16 1.332(5) . ?
C1 C2 1.528(6) . ?
C1 C10 1.539(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.524(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.542(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.551(5) . ?
C4 C17 1.521(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.532(6) . ?
C5 C10 1.564(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.516(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.536(5) . ?
C8 C9 1.552(5) . ?
C8 C14 1.558(6) . ?
C8 C19 1.553(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.545(5) . ?
C9 C11 1.566(5) . ?
C10 C18 1.548(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.511(6) . ?
C12 C13 1.537(6) . ?
C13 C14 1.558(5) . ?
C13 C20 1.520(7) . ?
C14 H14 0.9800 . ?
C14 C15 1.526(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.486(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C23 1.499(8) . ?
Cl4 C25 1.746(6) . ?
C25 H25 0.9800 . ?
C25 H25A 0.9800 . ?
C25 Cl5 1.764(8) . ?
C25 Cl6 1.775(8) . ?
C25 Cl5' 1.666(10) . ?
C25 Cl6' 1.742(7) . ?
Cl1 C24 1.723(8) . ?
Cl2 C24 1.764(6) . ?
Cl3 C24 1.751(7) . ?
C24 H24 0.9800 . ?
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
O1 C1 C2 O2 -4.3(6) . . . . ?
O1 C1 C2 C3 113.5(4) . . . . ?
O1 C1 C10 C5 -106.1(4) . . . . ?
O1 C1 C10 C9 10.2(5) . . . . ?
O1 C1 C10 C18 134.5(4) . . . . ?
O2 C2 C3 C4 168.7(3) . . . . ?
O3 C11 C12 O4 -21.3(5) . . . . ?
O3 C11 C12 C13 171.2(4) . . . . ?
O4 C12 C13 O6 134.3(4) . . . . ?
O4 C12 C13 C14 -112.0(4) . . . . ?
O4 C12 C13 C20 13.3(6) . . . . ?
O6 C13 C14 C8 69.5(4) . . . . ?
O6 C13 C14 C15 -164.8(3) . . . . ?
O8 C7 C8 C9 66.8(4) . . . . ?
O8 C7 C8 C14 -52.0(4) . . . . ?
O8 C7 C8 C19 -168.4(3) . . . . ?
C1 C2 C3 C4 47.7(5) . . . . ?
C2 C1 C10 C5 64.4(4) . . . . ?
C2 C1 C10 C9 -179.3(3) . . . . ?
C2 C1 C10 C18 -55.0(5) . . . . ?
C2 C3 C4 C5 -51.3(5) . . . . ?
C2 C3 C4 C17 -175.8(4) . . . . ?
C3 C4 C5 C6 -170.1(3) . . . . ?
C3 C4 C5 C10 61.7(4) . . . . ?
C4 C5 C6 C7 175.6(3) . . . . ?
C4 C5 C10 C1 -65.0(4) . . . . ?
C4 C5 C10 C9 179.3(3) . . . . ?
C4 C5 C10 C18 53.9(4) . . . . ?
C5 C6 C7 O8 -66.2(4) . . . . ?
C5 C6 C7 C8 57.7(4) . . . . ?
C6 C5 C10 C1 165.5(3) . . . . ?
C6 C5 C10 C9 49.9(4) . . . . ?
C6 C5 C10 C18 -75.5(4) . . . . ?
C6 C7 C8 C9 -51.4(4) . . . . ?
C6 C7 C8 C14 -170.2(3) . . . . ?
C6 C7 C8 C19 73.4(4) . . . . ?
C7 O8 C16 O7 167.4(4) . . . . ?
C7 O8 C16 C15 -17.3(6) . . . . ?
C7 C8 C9 C10 47.6(4) . . . . ?
C7 C8 C9 C11 179.1(3) . . . . ?
C7 C8 C14 C13 174.9(3) . . . . ?
C7 C8 C14 C15 51.0(4) . . . . ?
C8 C9 C10 C1 -157.2(3) . . . . ?
C8 C9 C10 C5 -47.0(4) . . . . ?
C8 C9 C10 C18 78.6(4) . . . . ?
C8 C9 C11 O3 -172.4(3) . . . . ?
C8 C9 C11 C12 65.0(4) . . . . ?
C8 C14 C15 C16 -34.7(5) . . . . ?
C9 C8 C14 C13 55.3(4) . . . . ?
C9 C8 C14 C15 -68.6(4) . . . . ?
C9 C11 C12 O4 103.6(4) . . . . ?
C9 C11 C12 C13 -63.9(4) . . . . ?
C10 C1 C2 O2 -175.1(3) . . . . ?
C10 C1 C2 C3 -57.3(4) . . . . ?
C10 C5 C6 C7 -56.5(4) . . . . ?
C10 C9 C11 O3 -39.6(5) . . . . ?
C10 C9 C11 C12 -162.2(3) . . . . ?
C11 C9 C10 C1 74.2(4) . . . . ?
C11 C9 C10 C5 -175.6(3) . . . . ?
C11 C9 C10 C18 -50.0(4) . . . . ?
C11 C12 C13 O6 -58.3(4) . . . . ?
C11 C12 C13 C14 55.3(5) . . . . ?
C11 C12 C13 C20 -179.4(4) . . . . ?
C12 C13 C14 C8 -48.8(5) . . . . ?
C12 C13 C14 C15 77.0(4) . . . . ?
C13 O6 C23 O5 9.8(8) . . . . ?
C13 O6 C23 C22 -172.6(5) . . . . ?
C13 C14 C15 C16 -161.4(4) . . . . ?
C14 C8 C9 C10 165.9(3) . . . . ?
C14 C8 C9 C11 -62.7(4) . . . . ?
C14 C15 C16 O7 -168.4(4) . . . . ?
C14 C15 C16 O8 16.4(6) . . . . ?
C16 O8 C7 C6 160.1(3) . . . . ?
C16 O8 C7 C8 36.8(5) . . . . ?
C17 C4 C5 C6 -48.0(5) . . . . ?
C17 C4 C5 C10 -176.2(4) . . . . ?
C19 C8 C9 C10 -69.8(4) . . . . ?
C19 C8 C9 C11 61.7(4) . . . . ?
C19 C8 C14 C13 -72.7(4) . . . . ?
C19 C8 C14 C15 163.4(3) . . . . ?
C20 C13 C14 C8 -173.0(4) . . . . ?
C20 C13 C14 C15 -47.2(5) . . . . ?
C21 O2 C2 C1 -75.4(5) . . . . ?
C21 O2 C2 C3 165.8(4) . . . . ?
C23 O6 C13 C12 -46.5(5) . . . . ?
C23 O6 C13 C14 -161.9(4) . . . . ?
C23 O6 C13 C20 76.8(5) . . . . ?
