#------------------------------------------------------------------------------
#$Date: 2021-09-04 03:19:03 +0300 (Sat, 04 Sep 2021) $
#$Revision: 268455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/45/1564534.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_1564534
loop_
_publ_author_name
'Huang, Chunshuai'
'Yang, Chunfang'
'Zhang, Wenjun'
'Zhang, Liping'
'Zhu, Yiguang'
'Zhang, Changsheng'
_publ_section_title
;
 Discovery of an Unexpected 1,4-Oxazepine-Linked seco-Fluostatin
 Heterodimer by Inactivation of the Oxidoreductase-Encoding Gene
 flsP.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2336
_journal_page_last               2344
_journal_paper_doi               10.1021/acs.jnatprod.1c00461
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H15 Cl O6, H2 O'
_chemical_formula_sum            'C19 H17 Cl O7'
_chemical_formula_weight         392.77
_chemical_name_systematic
(1R,2S,3R)-3-chloro-2,6,7-trihydroxy-1-methoxy-3-methyl-2,3-dihydro-1H-benzo[a]fluorene-4,11-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1790(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.86876(5)
_cell_length_b                   11.85008(7)
_cell_length_c                   21.07510(10)
_cell_measurement_reflns_used    24402
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9830
_cell_measurement_theta_min      4.2230
_cell_volume                     1697.967(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -116.00 -18.00   1.00    1.00    --  -41.89 -37.00 120.00   98
  2  ω   -116.00 -18.00   1.00    1.00    --  -41.89 -37.00 150.00   98
  3  ω    -74.00  34.00   1.00    1.00    --  -41.89  77.00 120.00  108
  4  ω    -33.00  66.00   1.00    1.00    --   41.89 -37.00-150.00   99
  5  ω     23.00  98.00   1.00    1.00    --   41.89-125.00   0.00   75
  6  ω     18.00 116.00   1.00    1.00    --   41.89  37.00  60.00   98
  7  ω     29.00 103.00   1.00    1.00    --   41.89-134.00 131.00   74
  8  ω     32.00 140.00   1.00    2.00    --  107.79 -77.00 -30.00  108
  9  ω     32.00 136.00   1.00    2.00    --  107.79 -30.00 120.00  104
 10  ω     80.00 178.00   1.00    2.00    --  107.79  30.00  30.00   98
 11  ω     32.00 136.00   1.00    2.00    --  107.79 -30.00  30.00  104
 12  ω     35.00 134.00   1.00    2.00    --  107.79 -45.00-150.00   99
 13  ω     25.00 109.00   1.00    2.00    --  107.79 -94.00 -30.00   84
 14  ω     35.00 122.00   1.00    2.00    --  107.79-125.00-180.00   87
 15  ω     80.00 178.00   1.00    2.00    --  107.79  30.00  90.00   98
 16  ω     94.00 178.00   1.00    2.00    --  107.79 125.00  60.00   84
 17  ω     55.00 178.00   1.00    2.00    --  107.79  15.00 -60.00  123
 18  ω    101.00 178.00   1.00    2.00    --  107.79  96.00 -51.00   77
 19  ω     25.00 109.00   1.00    2.00    --  107.79 -94.00-150.00   84
 20  ω   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00  90.00  109
 21  ω   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00   0.00  101
 22  ω   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00 -60.00  109
 23  ω    -66.00  33.00   1.00    1.00    --  -41.89  37.00  60.00   99
 24  ω      9.00 118.00   1.00    1.00    --   41.89  77.00-150.00  109
 25  ω     75.00 178.00   1.00    2.00    --  107.79  77.00 120.00  103
 26  ω     79.00 178.00   1.00    2.00    --  107.79  61.00 -90.00   99
 27  ω     82.00 178.00   1.00    2.00    --  107.79  45.00-180.00   96
 28  ω     79.00 178.00   1.00    2.00    --  107.79  61.00  30.00   99
 29  ω     75.00 178.00   1.00    2.00    --  107.79  77.00  90.00  103
 30  ω     75.00 178.00   1.00    2.00    --  107.79  77.00-180.00  103
 31  ω     75.00 162.00   1.00    2.00    --  107.79  77.00 -30.00   87
 32  ω     75.00 178.00   1.00    2.00    --  107.79  77.00 -60.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0525637000
_diffrn_orient_matrix_UB_12      0.0327824000
_diffrn_orient_matrix_UB_13      -0.0710994000
_diffrn_orient_matrix_UB_21      -0.0655808000
_diffrn_orient_matrix_UB_22      0.1174949000
_diffrn_orient_matrix_UB_23      0.0199463000
_diffrn_orient_matrix_UB_31      0.2105000000
_diffrn_orient_matrix_UB_32      0.0448663000
_diffrn_orient_matrix_UB_33      -0.0002368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.042
_diffrn_reflns_theta_min         4.239
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6802
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                6735
_reflns_number_total             6802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00461_si_002.cif
_cod_data_source_block           1611013
_cod_original_cell_volume        1697.968(18)
_cod_database_code               1564534
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     Y20-6
_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 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O25(H25A,H25B)
2.b Free rotating group:
 O26(H26A,H26B)
2.c Ternary CH refined with riding coordinates:
 C1(H1), C1'(H1'), C3(H2A), C2'(H2')
2.d Aromatic/amide H refined with riding coordinates:
 C5'(H5'), C5(H5), C10(H10), C10'(H10'), C8'(H8'), C9(H8), C9'(H9'), C14(H9)
2.e Idealised Me refined as rotating group:
 C13(H13D,H13E,H13F), C12'(H12A,H12B,H12C), C12(H12D,H12E,H12F), C13'(H13A,
 H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O19(H19), O20(H20), O2(H2), O15(H15), O6(H6), O7(H7)
;
_olex2_submission_original_sample_id Y20-6
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.735
_oxdiff_exptl_absorpt_empirical_full_min 0.553
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
Cl2 Cl 0.58198(9) 0.56454(5) 0.46555(3) 0.02725(13) Uani 1 1 d . . . . .
Cl1 Cl 0.47222(9) 0.12823(6) 0.29435(3) 0.03374(15) Uani 1 1 d . . . . .
O26 O 0.6424(3) 0.27577(14) 0.16058(8) 0.0240(3) Uani 1 1 d G . . . .
H26A H 0.709846 0.245593 0.193026 0.036 Uiso 1 1 d G U . . .
H26B H 0.522323 0.257379 0.159138 0.036 Uiso 1 1 d G U . . .
O19 O 0.6629(3) 0.48945(14) 0.14331(8) 0.0244(4) Uani 1 1 d . . . . .
H19 H 0.660629 0.420204 0.151681 0.037 Uiso 1 1 calc R U . . .
O1 O 0.2770(2) 0.20430(14) 0.15868(7) 0.0197(3) Uani 1 1 d . . . . .
O20 O 0.6200(3) 0.63158(16) 0.04501(7) 0.0266(4) Uani 1 1 d . . . . .
H20 H 0.644375 0.579121 0.071764 0.040 Uiso 1 1 calc R U . . .
O24 O 0.7802(3) 0.92940(14) 0.27488(8) 0.0231(3) Uani 1 1 d . . . . .
O14 O 0.5994(3) 0.77894(14) 0.38441(8) 0.0236(3) Uani 1 1 d . . . . .
O2 O -0.1126(2) 0.14985(14) 0.25186(8) 0.0225(3) Uani 1 1 d . . . . .
H2 H -0.152354 0.087999 0.264660 0.034 Uiso 1 1 calc R U . . .
O15 O 1.1007(3) 0.67300(16) 0.42498(8) 0.0249(4) Uani 1 1 d . . . . .
H15 H 1.170555 0.679941 0.460866 0.037 Uiso 1 1 calc R U . . .
O6 O 0.2503(3) 0.66504(14) 0.31428(8) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.220908 0.662691 0.351616 0.040 Uiso 1 1 calc R U . . .
O11 O 0.0794(3) 0.39133(15) 0.08020(8) 0.0271(4) Uani 1 1 d . . . . .
O17 O 0.7747(3) 0.39028(15) 0.37542(8) 0.0321(4) Uani 1 1 d . . . . .
O7 O 0.2575(4) 0.82083(15) 0.22446(10) 0.0362(5) Uani 1 1 d . . . . .
H7 H 0.267475 0.779441 0.257122 0.054 Uiso 1 1 calc R U . . .
O4 O 0.2253(4) 0.26609(17) 0.39565(8) 0.0416(5) Uani 1 1 d . . . . .
O25 O 1.2981(4) 0.7129(2) 0.54268(10) 0.0480(6) Uani 1 1 d . . . . .
H25A H 1.247081 0.772526 0.557913 0.072 Uiso 1 1 d R U . . .
H25B H 1.423701 0.719126 0.555483 0.072 Uiso 1 1 d R U . . .
C10A C 0.1410(3) 0.58594(19) 0.11069(11) 0.0194(5) Uani 1 1 d . . . . .
C11' C 0.7457(3) 0.85087(19) 0.23780(10) 0.0180(4) Uani 1 1 d . . . . .
C4A' C 0.7543(3) 0.55825(19) 0.31512(10) 0.0166(4) Uani 1 1 d . . . . .
C24A C 0.7395(3) 0.72787(18) 0.25432(10) 0.0163(4) Uani 1 1 d . . . . .
C6A C 0.2003(3) 0.55211(19) 0.22064(10) 0.0167(4) Uani 1 1 d . . . . .
C4A C 0.2041(3) 0.35686(19) 0.29494(10) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.2124(4) 0.2577(2) 0.33775(11) 0.0232(5) Uani 1 1 d . . . . .
C6A' C 0.7045(3) 0.66660(18) 0.19667(10) 0.0160(4) Uani 1 1 d . . . . .
C5' C 0.7186(3) 0.49609(18) 0.25826(10) 0.0174(4) Uani 1 1 d . . . . .
H5' H 0.710872 0.416155 0.260274 0.021 Uiso 1 1 calc R U . . .
C4' C 0.7835(4) 0.4926(2) 0.37559(10) 0.0197(5) Uani 1 1 d . . . . .
C6' C 0.6943(3) 0.54919(19) 0.19886(10) 0.0166(4) Uani 1 1 d . . . . .
C11B C 0.1692(3) 0.34624(19) 0.22749(10) 0.0157(4) Uani 1 1 d . . . . .
C11A C 0.1688(3) 0.44537(19) 0.19240(10) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.1244(3) 0.46231(19) 0.12076(10) 0.0188(4) Uani 1 1 d . . . . .
C1 C 0.1232(3) 0.23367(18) 0.19441(10) 0.0157(4) Uani 1 1 d . . . . .
H1 H 0.000245 0.243392 0.163262 0.019 Uiso 1 1 calc R U . . .
C24B C 0.7657(3) 0.67676(19) 0.31427(10) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.2103(4) 0.7569(2) 0.17129(12) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.7051(3) 0.8564(2) 0.16661(11) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.2289(3) 0.5606(2) 0.28745(10) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.2320(3) 0.4630(2) 0.32358(10) 0.0198(4) Uani 1 1 d . . . . .
H5 H 0.253655 0.468307 0.369014 0.024 Uiso 1 1 calc R U . . .
C7' C 0.6445(3) 0.7319(2) 0.07543(11) 0.0206(5) Uani 1 1 d . . . . .
C10 C 0.1164(4) 0.6429(2) 0.05288(11) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.085625 0.603839 0.013379 0.029 Uiso 1 1 calc R U . . .
C1' C 0.7915(4) 0.74485(19) 0.37569(10) 0.0191(4) Uani 1 1 d . . . . .
H1' H 0.870617 0.813706 0.369269 0.023 Uiso 1 1 calc R U . . .
C3' C 0.8239(4) 0.5563(2) 0.43939(10) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.0867(3) 0.13830(19) 0.24052(10) 0.0177(4) Uani 1 1 d . . . . .
H2A H 0.103277 0.063887 0.219558 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2165(3) 0.1413(2) 0.30618(10) 0.0207(4) Uani 1 1 d . . . . .
C6B' C 0.6833(3) 0.74646(19) 0.14184(11) 0.0177(4) Uani 1 1 d . . . . .
C2' C 0.8983(3) 0.6780(2) 0.43281(10) 0.0193(4) Uani 1 1 d . . . . .
H2' H 0.886063 0.720085 0.473185 0.023 Uiso 1 1 calc R U . . .
C6B C 0.1872(3) 0.6401(2) 0.17023(11) 0.0191(4) Uani 1 1 d . . . . .
C10' C 0.6896(4) 0.9521(2) 0.12867(11) 0.0242(5) Uani 1 1 d . . . . .
H10' H 0.705336 1.025460 0.146817 0.029 Uiso 1 1 calc R U . . .
C8' C 0.6286(4) 0.8286(2) 0.03663(11) 0.0259(5) Uani 1 1 d . . . . .
H8' H 0.602560 0.819987 -0.008601 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1853(4) 0.8143(2) 0.11267(14) 0.0287(5) Uani 1 1 d . . . . .
H8 H 0.201135 0.893898 0.112776 0.034 Uiso 1 1 calc R U . . .
C9' C 0.6494(4) 0.9358(2) 0.06209(12) 0.0273(5) Uani 1 1 d . . . . .
H9' H 0.636566 0.999295 0.034306 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2076(4) 0.1419(2) 0.10170(11) 0.0259(5) Uani 1 1 d . . . . .
H13D H 0.130526 0.191687 0.070571 0.039 Uiso 1 1 calc R U . . .
H13E H 0.124752 0.079285 0.112353 0.039 Uiso 1 1 calc R U . . .
H13F H 0.320066 0.111905 0.083206 0.039 Uiso 1 1 calc R U . . .
C12' C 0.9577(4) 0.4895(2) 0.48892(11) 0.0275(5) Uani 1 1 d . . . . .
H12A H 0.992280 0.535514 0.527514 0.041 Uiso 1 1 calc R U . . .
H12B H 1.077667 0.468756 0.471487 0.041 Uiso 1 1 calc R U . . .
H12C H 0.889887 0.420949 0.499845 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1700(4) 0.0468(2) 0.34976(12) 0.0312(6) Uani 1 1 d . . . . .
H12D H 0.187049 -0.025948 0.329116 0.047 Uiso 1 1 calc R U . . .
H12E H 0.033764 0.053996 0.358066 0.047 Uiso 1 1 calc R U . . .
H12F H 0.259126 0.050992 0.390370 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1384(4) 0.7594(2) 0.05462(13) 0.0289(5) Uani 1 1 d . . . . .
H9 H 0.121204 0.801494 0.015857 0.035 Uiso 1 1 calc R U . . .
C13' C 0.5953(5) 0.8715(2) 0.42733(13) 0.0356(6) Uani 1 1 d . . . . .
H13A H 0.660690 0.936718 0.411030 0.053 Uiso 1 1 calc R U . . .
H13B H 0.663975 0.850621 0.469675 0.053 Uiso 1 1 calc R U . . .
H13C H 0.458544 0.890898 0.430804 0.053 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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H26A O26 H26B 109.7 . . ?
C6' O19 H19 109.5 . . ?
C1 O1 C13 112.71(17) . . ?
C7' O20 H20 109.5 . . ?
C1' O14 C13' 113.8(2) . . ?
C3 O2 H2 109.5 . . ?
C2' O15 H15 109.5 . . ?
C6 O6 H6 109.5 . . ?
C7 O7 H7 109.5 . . ?
H25A O25 H25B 104.5 . . ?
C10 C10A C11 127.2(2) . . ?
C10 C10A C6B 123.2(2) . . ?
C6B C10A C11 109.55(19) . . ?
O24 C11' C24A 127.1(2) . . ?
O24 C11' C2 127.3(2) . . ?
C2 C11' C24A 105.60(19) . . ?
C5' C4A' C4' 116.5(2) . . ?
C5' C4A' C24B 121.2(2) . . ?
C24B C4A' C4' 122.3(2) . . ?
C6A' C24A C11' 107.94(18) . . ?
C24B C24A C11' 129.1(2) . . ?
C24B C24A C6A' 123.0(2) . . ?
C11A C6A C6B 109.91(19) . . ?
C6 C6A C11A 119.0(2) . . ?
C6 C6A C6B 131.1(2) . . ?
C11B C4A C4 122.0(2) . . ?
C5 C4A C4 117.49(19) . . ?
C5 C4A C11B 120.5(2) . . ?
O4 C4 C4A 122.6(2) . . ?
O4 C4 C8 120.5(2) . . ?
C4A C4 C8 116.86(19) . . ?
C24A C6A' C6B' 109.21(19) . . ?
C6' C6A' C24A 119.3(2) . . ?
C6' C6A' C6B' 131.5(2) . . ?
C4A' C5' H5' 119.4 . . ?
C6' C5' C4A' 121.2(2) . . ?
C6' C5' H5' 119.4 . . ?
O17 C4' C4A' 121.4(2) . . ?
O17 C4' C3' 119.8(2) . . ?
C4A' C4' C3' 118.8(2) . . ?
O19 C6' C6A' 119.60(19) . . ?
O19 C6' C5' 121.6(2) . . ?
C5' C6' C6A' 118.8(2) . . ?
C4A C11B C1 122.33(19) . . ?
C11A C11B C4A 116.6(2) . . ?
C11A C11B C1 120.98(18) . . ?
C6A C11A C11 107.55(19) . . ?
C11B C11A C6A 123.31(19) . . ?
C11B C11A C11 129.0(2) . . ?
O11 C11 C10A 127.0(2) . . ?
O11 C11 C11A 127.6(2) . . ?
C10A C11 C11A 105.36(18) . . ?
O1 C1 C11B 109.63(17) . . ?
O1 C1 H1 107.5 . . ?
O1 C1 C3 110.81(17) . . ?
C11B C1 H1 107.5 . . ?
C11B C1 C3 113.50(17) . . ?
C3 C1 H1 107.5 . . ?
C4A' C24B C1' 121.40(19) . . ?
C24A C24B C4A' 116.5(2) . . ?
C24A C24B C1' 122.0(2) . . ?
O7 C7 C6B 125.7(2) . . ?
O7 C7 C9 116.3(2) . . ?
C6B C7 C9 118.0(2) . . ?
C6B' C2 C11' 109.23(19) . . ?
C10' C2 C11' 127.4(2) . . ?
C10' C2 C6B' 123.4(2) . . ?
O6 C6 C6A 118.5(2) . . ?
O6 C6 C5 122.67(19) . . ?
C5 C6 C6A 118.9(2) . . ?
C4A C5 H5 119.2 . . ?
C6 C5 C4A 121.66(19) . . ?
C6 C5 H5 119.2 . . ?
O20 C7' C6B' 125.3(2) . . ?
O20 C7' C8' 116.6(2) . . ?
C6B' C7' C8' 118.1(2) . . ?
C10A C10 H10 121.2 . . ?
C10A C10 C14 117.6(2) . . ?
C14 C10 H10 121.2 . . ?
O14 C1' C24B 105.35(18) . . ?
O14 C1' H1' 108.6 . . ?
O14 C1' C2' 113.25(18) . . ?
C24B C1' H1' 108.6 . . ?
C24B C1' C2' 112.31(18) . . ?
C2' C1' H1' 108.6 . . ?
C4' C3' Cl2 103.44(16) . . ?
C4' C3' C2' 113.73(18) . . ?
C2' C3' Cl2 107.71(16) . . ?
C12' C3' Cl2 108.02(16) . . ?
C12' C3' C4' 111.4(2) . . ?
C12' C3' C2' 112.0(2) . . ?
O2 C3 C1 106.40(17) . . ?
O2 C3 H2A 109.3 . . ?
O2 C3 C8 107.09(17) . . ?
C1 C3 H2A 109.3 . . ?
C1 C3 C8 115.27(18) . . ?
C8 C3 H2A 109.3 . . ?
C4 C8 Cl1 102.39(16) . . ?
C4 C8 C3 111.60(19) . . ?
C3 C8 Cl1 108.85(15) . . ?
C12 C8 Cl1 108.18(18) . . ?
C12 C8 C4 112.61(19) . . ?
C12 C8 C3 112.6(2) . . ?
C2 C6B' C6A' 107.97(19) . . ?
C7' C6B' C6A' 133.2(2) . . ?
C7' C6B' C2 118.8(2) . . ?
O15 C2' C1' 107.18(18) . . ?
O15 C2' C3' 108.22(18) . . ?
O15 C2' H2' 108.7 . . ?
C1' C2' C3' 115.15(19) . . ?
C1' C2' H2' 108.7 . . ?
C3' C2' H2' 108.7 . . ?
C10A C6B C6A 107.6(2) . . ?
C7 C6B C10A 118.6(2) . . ?
C7 C6B C6A 133.8(2) . . ?
C2 C10' H10' 121.5 . . ?
C2 C10' C9' 116.9(2) . . ?
C9' C10' H10' 121.5 . . ?
C7' C8' H8' 119.0 . . ?
C9' C8' C7' 122.1(2) . . ?
C9' C8' H8' 119.0 . . ?
C7 C9 H8 118.8 . . ?
C14 C9 C7 122.5(2) . . ?
C14 C9 H8 118.8 . . ?
C10' C9' H9' 119.6 . . ?
C8' C9' C10' 120.7(2) . . ?
C8' C9' H9' 119.6 . . ?
O1 C13 H13D 109.5 . . ?
O1 C13 H13E 109.5 . . ?
O1 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C3' C12' H12A 109.5 . . ?
C3' C12' H12B 109.5 . . ?
C3' C12' H12C 109.5 . . ?
H12A C12' H12B 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
C8 C12 H12D 109.5 . . ?
C8 C12 H12E 109.5 . . ?
C8 C12 H12F 109.5 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C10 C14 H9 120.0 . . ?
C9 C14 C10 120.1(2) . . ?
C9 C14 H9 120.0 . . ?
O14 C13' H13A 109.5 . . ?
O14 C13' H13B 109.5 . . ?
O14 C13' H13C 109.5 . . ?
H13A C13' H13B 109.5 . . ?
H13A C13' H13C 109.5 . . ?
H13B C13' H13C 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
Cl2 C3' 1.826(2) . ?
Cl1 C8 1.816(2) . ?
O26 H26A 0.8484 . ?
O26 H26B 0.8494 . ?
O19 H19 0.8400 . ?
O19 C6' 1.359(3) . ?
O1 C1 1.425(3) . ?
O1 C13 1.433(3) . ?
O20 H20 0.8400 . ?
O20 C7' 1.349(3) . ?
O24 C11' 1.217(3) . ?
O14 C1' 1.417(3) . ?
O14 C13' 1.425(3) . ?
O2 H2 0.8400 . ?
O2 C3 1.429(3) . ?
O15 H15 0.8400 . ?
O15 C2' 1.425(3) . ?
O6 H6 0.8400 . ?
O6 C6 1.359(3) . ?
O11 C11 1.208(3) . ?
O17 C4' 1.214(3) . ?
O7 H7 0.8400 . ?
O7 C7 1.354(3) . ?
O4 C4 1.215(3) . ?
O25 H25A 0.8700 . ?
O25 H25B 0.8700 . ?
C10A C11 1.487(3) . ?
C10A C10 1.382(3) . ?
C10A C6B 1.405(3) . ?
C11' C24A 1.501(3) . ?
C11' C2 1.488(3) . ?
C4A' C5' 1.398(3) . ?
C4A' C4' 1.482(3) . ?
C4A' C24B 1.407(3) . ?
C24A C6A' 1.406(3) . ?
C24A C24B 1.390(3) . ?
C6A C11A 1.401(3) . ?
C6A C6 1.397(3) . ?
C6A C6B 1.482(3) . ?
C4A C4 1.478(3) . ?
C4A C11B 1.413(3) . ?
C4A C5 1.397(3) . ?
C4 C8 1.532(3) . ?
C6A' C6' 1.394(3) . ?
C6A' C6B' 1.485(3) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.390(3) . ?
C4' C3' 1.532(3) . ?
C11B C11A 1.388(3) . ?
C11B C1 1.517(3) . ?
C11A C11 1.511(3) . ?
C1 H1 1.0000 . ?
C1 C3 1.534(3) . ?
C24B C1' 1.514(3) . ?
C7 C6B 1.393(3) . ?
C7 C9 1.399(4) . ?
C2 C6B' 1.403(3) . ?
C2 C10' 1.383(3) . ?
C6 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C7' C6B' 1.398(3) . ?
C7' C8' 1.404(3) . ?
C10 H10 0.9500 . ?
C10 C14 1.388(4) . ?
C1' H1' 1.0000 . ?
C1' C2' 1.537(3) . ?
C3' C2' 1.543(3) . ?
C3' C12' 1.513(3) . ?
C3 H2A 1.0000 . ?
C3 C8 1.536(3) . ?
C8 C12 1.511(3) . ?
C2' H2' 1.0000 . ?
C10' H10' 0.9500 . ?
C10' C9' 1.404(4) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.378(4) . ?
C9 H8 0.9500 . ?
C9 C14 1.382(4) . ?
C9' H9' 0.9500 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C12' H12A 0.9800 . ?
C12' H12B 0.9800 . ?
C12' H12C 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?
C14 H9 0.9500 . ?
C13' H13A 0.9800 . ?
C13' H13B 0.9800 . ?
C13' H13C 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
_geom_hbond_publ_flag
O26 H26A O2 0.85 1.97 2.800(2) 165.5 1_655 yes
O26 H26B O1 0.85 1.80 2.644(2) 174.1 . yes
O19 H19 O26 0.84 1.73 2.565(2) 173.8 . yes
O20 H20 O19 0.84 1.83 2.654(2) 164.7 . yes
O2 H2 O24 0.84 1.95 2.775(2) 165.3 1_445 yes
O15 H15 O25 0.84 1.86 2.694(3) 171.1 . yes
O6 H6 O15 0.84 1.86 2.681(2) 166.4 1_455 yes
O7 H7 O6 0.84 1.83 2.650(3) 165.3 . yes
O25 H25A O17 0.87 2.00 2.809(3) 154.1 2_756 yes
C1 H1 O26 1.00 2.48 3.316(3) 140.8 1_455 yes
C1' H1' O24 1.00 2.42 3.042(3) 119.5 . yes
C13 H13D O11 0.98 2.40 3.099(3) 127.4 . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 C3' C2' O15 168.63(13) . . . . ?
Cl2 C3' C2' C1' -71.5(2) . . . . ?
O1 C1 C3 O2 -154.76(17) . . . . ?
O1 C1 C3 C8 86.7(2) . . . . ?
O20 C7' C6B' C6A' -1.6(4) . . . . ?
O20 C7' C6B' C2 -180.0(2) . . . . ?
O20 C7' C8' C9' 179.6(2) . . . . ?
O24 C11' C24A C6A' -177.0(2) . . . . ?
O24 C11' C24A C24B 1.9(4) . . . . ?
O24 C11' C2 C6B' 176.9(2) . . . . ?
O24 C11' C2 C10' -3.2(4) . . . . ?
O14 C1' C2' O15 -166.29(17) . . . . ?
O14 C1' C2' C3' 73.3(2) . . . . ?
O2 C3 C8 Cl1 -179.48(14) . . . . ?
O2 C3 C8 C4 -67.2(2) . . . . ?
O2 C3 C8 C12 60.6(2) . . . . ?
O6 C6 C5 C4A 178.1(2) . . . . ?
O17 C4' C3' Cl2 -82.6(3) . . . . ?
O17 C4' C3' C2' 160.8(2) . . . . ?
O17 C4' C3' C12' 33.2(3) . . . . ?
O7 C7 C6B C10A -178.9(2) . . . . ?
O7 C7 C6B C6A 1.2(5) . . . . ?
O7 C7 C9 C14 179.5(2) . . . . ?
O4 C4 C8 Cl1 -97.0(3) . . . . ?
O4 C4 C8 C3 146.7(3) . . . . ?
O4 C4 C8 C12 18.9(4) . . . . ?
C10A C10 C14 C9 0.7(4) . . . . ?
C11' C24A C6A' C6' 179.3(2) . . . . ?
C11' C24A C6A' C6B' -1.1(2) . . . . ?
C11' C24A C24B C4A' -179.1(2) . . . . ?
C11' C24A C24B C1' 4.8(4) . . . . ?
C11' C2 C6B' C6A' 1.4(3) . . . . ?
C11' C2 C6B' C7' -179.9(2) . . . . ?
C11' C2 C10' C9' -179.8(2) . . . . ?
C4A' C5' C6' O19 178.8(2) . . . . ?
C4A' C5' C6' C6A' -0.5(3) . . . . ?
C4A' C4' C3' Cl2 96.9(2) . . . . ?
C4A' C4' C3' C2' -19.7(3) . . . . ?
C4A' C4' C3' C12' -147.3(2) . . . . ?
C4A' C24B C1' O14 -96.3(2) . . . . ?
C4A' C24B C1' C2' 27.4(3) . . . . ?
C24A C11' C2 C6B' -2.0(3) . . . . ?
C24A C11' C2 C10' 177.9(2) . . . . ?
C24A C6A' C6' O19 -179.2(2) . . . . ?
C24A C6A' C6' C5' 0.2(3) . . . . ?
C24A C6A' C6B' C2 -0.2(3) . . . . ?
C24A C6A' C6B' C7' -178.7(2) . . . . ?
C24A C24B C1' O14 79.5(3) . . . . ?
C24A C24B C1' C2' -156.8(2) . . . . ?
C6A C11A C11 O11 -175.9(2) . . . . ?
C6A C11A C11 C10A 2.1(2) . . . . ?
C6A C6 C5 C4A -1.1(3) . . . . ?
C4A C4 C8 Cl1 79.5(2) . . . . ?
C4A C4 C8 C3 -36.8(3) . . . . ?
C4A C4 C8 C12 -164.5(2) . . . . ?
C4A C11B C11A C6A -0.1(3) . . . . ?
C4A C11B C11A C11 -176.0(2) . . . . ?
C4A C11B C1 O1 -115.4(2) . . . . ?
C4A C11B C1 C3 9.1(3) . . . . ?
C4 C4A C11B C11A -178.7(2) . . . . ?
C4 C4A C11B C1 4.6(3) . . . . ?
C4 C4A C5 C6 179.3(2) . . . . ?
C6A' C24A C24B C4A' -0.4(3) . . . . ?
C6A' C24A C24B C1' -176.4(2) . . . . ?
C5' C4A' C4' O17 -0.7(4) . . . . ?
C5' C4A' C4' C3' 179.8(2) . . . . ?
C5' C4A' C24B C24A 0.1(3) . . . . ?
C5' C4A' C24B C1' 176.1(2) . . . . ?
C4' C4A' C5' C6' -178.3(2) . . . . ?
C4' C4A' C24B C24A 178.7(2) . . . . ?
C4' C4A' C24B C1' -5.3(4) . . . . ?
C4' C3' C2' O15 -77.4(2) . . . . ?
C4' C3' C2' C1' 42.5(3) . . . . ?
C6' C6A' C6B' C2 179.5(2) . . . . ?
C6' C6A' C6B' C7' 1.0(4) . . . . ?
C11B C4A C4 O4 -173.5(3) . . . . ?
C11B C4A C4 C8 10.1(3) . . . . ?
C11B C4A C5 C6 -0.7(4) . . . . ?
C11B C11A C11 O11 0.4(4) . . . . ?
C11B C11A C11 C10A 178.5(2) . . . . ?
C11B C1 C3 O2 81.4(2) . . . . ?
C11B C1 C3 C8 -37.2(3) . . . . ?
C11A C6A C6 O6 -177.0(2) . . . . ?
C11A C6A C6 C5 2.2(3) . . . . ?
C11A C6A C6B C10A 1.8(3) . . . . ?
C11A C6A C6B C7 -178.3(3) . . . . ?
C11A C11B C1 O1 68.0(3) . . . . ?
C11A C11B C1 C3 -167.5(2) . . . . ?
C11 C10A C10 C14 179.9(2) . . . . ?
C11 C10A C6B C6A -0.4(3) . . . . ?
C11 C10A C6B C7 179.7(2) . . . . ?
C1 C11B C11A C6A 176.6(2) . . . . ?
C1 C11B C11A C11 0.8(4) . . . . ?
C1 C3 C8 Cl1 -61.3(2) . . . . ?
C1 C3 C8 C4 50.9(2) . . . . ?
C1 C3 C8 C12 178.7(2) . . . . ?
C24B C4A' C5' C6' 0.4(4) . . . . ?
C24B C4A' C4' O17 -179.4(2) . . . . ?
C24B C4A' C4' C3' 1.1(4) . . . . ?
C24B C24A C6A' C6' 0.3(3) . . . . ?
C24B C24A C6A' C6B' 180.0(2) . . . . ?
C24B C1' C2' O15 74.5(2) . . . . ?
C24B C1' C2' C3' -45.9(3) . . . . ?
C7 C9 C14 C10 -0.7(4) . . . . ?
C2 C11' C24A C6A' 1.8(2) . . . . ?
C2 C11' C24A C24B -179.3(2) . . . . ?
C2 C10' C9' C8' -0.5(4) . . . . ?
C6 C6A C11A C11B -1.7(3) . . . . ?
C6 C6A C11A C11 175.0(2) . . . . ?
C6 C6A C6B C10A -175.1(2) . . . . ?
C6 C6A C6B C7 4.8(4) . . . . ?
C5 C4A C4 O4 6.5(4) . . . . ?
C5 C4A C4 C8 -170.0(2) . . . . ?
C5 C4A C11B C11A 1.3(3) . . . . ?
C5 C4A C11B C1 -175.4(2) . . . . ?
C7' C8' C9' C10' 0.5(4) . . . . ?
C10 C10A C11 O11 -3.0(4) . . . . ?
C10 C10A C11 C11A 178.9(2) . . . . ?
C10 C10A C6B C6A 179.7(2) . . . . ?
C10 C10A C6B C7 -0.3(4) . . . . ?
C6B' C6A' C6' O19 1.2(4) . . . . ?
C6B' C6A' C6' C5' -179.4(2) . . . . ?
C6B' C2 C10' C9' 0.1(4) . . . . ?
C6B' C7' C8' C9' -0.2(4) . . . . ?
C6B C10A C11 O11 177.1(2) . . . . ?
C6B C10A C11 C11A -1.0(2) . . . . ?
C6B C10A C10 C14 -0.2(4) . . . . ?
C6B C6A C11A C11B -179.1(2) . . . . ?
C6B C6A C11A C11 -2.4(2) . . . . ?
C6B C6A C6 O6 -0.3(4) . . . . ?
C6B C6A C6 C5 179.0(2) . . . . ?
C6B C7 C9 C14 0.2(4) . . . . ?
C10' C2 C6B' C6A' -178.5(2) . . . . ?
C10' C2 C6B' C7' 0.2(4) . . . . ?
C8' C7' C6B' C6A' 178.2(2) . . . . ?
C8' C7' C6B' C2 -0.2(3) . . . . ?
C9 C7 C6B C10A 0.2(4) . . . . ?
C9 C7 C6B C6A -179.6(2) . . . . ?
C13 O1 C1 C11B -147.38(18) . . . . ?
C13 O1 C1 C3 86.6(2) . . . . ?
C12' C3' C2' O15 50.0(2) . . . . ?
C12' C3' C2' C1' 169.85(19) . . . . ?
C13' O14 C1' C24B -161.3(2) . . . . ?
C13' O14 C1' C2' 75.5(3) . . . . ?
