#------------------------------------------------------------------------------
#$Date: 2022-02-04 02:45:59 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272523 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/62/1566291.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_1566291
loop_
_publ_author_name
'Cao, Hai-Yan'
'Yi, Cheng'
'Sun, Sen-Feng'
'Li, Yong'
'Liu, Yun-Bao'
_publ_section_title
;
 Anti-inflammatory Dimeric Tetrahydroxanthones from an Endophytic
 Muyocopron laterale.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              148
_journal_page_last               161
_journal_paper_doi               10.1021/acs.jnatprod.1c00878
_journal_volume                  85
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H34 O12'
_chemical_formula_sum            'C32 H34 O12'
_chemical_formula_weight         610.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.08670(10)
_cell_length_b                   10.26000(10)
_cell_length_c                   17.8397(2)
_cell_measurement_reflns_used    35690
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7940
_cell_measurement_theta_min      4.3660
_cell_volume                     1455.00(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     24.00 120.00   0.50    0.05    --   47.70  80.00  19.00  192
  2  ω     87.00 176.00   0.50    0.05    --  103.25  61.00 -60.00  178
  3  ω     79.00 176.00   0.50    0.05    --  103.25  80.00  19.00  194
  4  ω     91.00 178.00   0.50    0.05    --  103.25  30.00   0.00  174
  5  ω     91.00 175.00   0.50    0.05    --  103.25  45.00  60.00  168
  6  ω     90.00 178.00   0.50    0.05    --  103.25  15.00 120.00  176
  7  ω     91.00 178.00   0.50    0.05    --  103.25  30.00 150.00  174
  8  ω     90.00 178.00   0.50    0.05    --  103.25  15.00 150.00  176
  9  ω    -23.00  28.00   0.50    0.05    --  -47.70  19.00   0.00  102
 10  ω    -39.00  26.00   0.50    0.05    --  -47.70  37.00   0.00  130
 11  ω    -72.00  25.00   0.50    0.05    --  -47.70  80.00  19.00  194
 12  ω    -23.00  28.00   0.50    0.05    --  -47.70  19.00 150.00  102
 13  ω   -125.00 -28.00   0.50    0.05    -- -101.00  80.00  19.00  194
 14  ω    -68.00 -28.00   0.50    0.05    -- -101.00  61.00  90.00   80
 15  ω    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -30.00   80
 16  ω    -68.00 -28.00   0.50    0.05    -- -101.00  61.00-120.00   80
 17  ω   -102.00 -28.00   0.50    0.05    -- -101.00  77.00-150.00  148
 18  ω   -174.00 -88.00   0.50    0.05    -- -101.00 -30.00 -60.00  172
 19  ω   -173.00 -77.00   0.50    0.05    -- -101.00 -80.00-104.00  192
 20  ω   -119.00 -24.00   0.50    0.05    --  -47.70 -80.00-104.00  190
 21  ω   -173.00 -88.00   0.50    0.05    -- -101.00 -45.00 120.00  170
 22  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 150.00  188
 23  ω   -119.00 -74.00   0.50    0.05    --  -47.70-125.00 120.00   90
 24  ω   -119.00 -74.00   0.50    0.05    --  -47.70-125.00  60.00   90
 25  ω   -173.00 -74.00   0.50    0.05    -- -101.00-125.00   0.00  198
 26  ω   -173.00 -84.00   0.50    0.05    -- -101.00 -94.00-150.00  178
 27  ω   -119.00 -74.00   0.50    0.05    --  -47.70-125.00-120.00   90
 28  ω    -24.00  72.00   0.50    0.05    --   47.70 -80.00-104.00  192
 29  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00 -30.00   88
 30  ω     31.00 127.00   0.50    0.05    --  103.25 -80.00-104.00  192
 31  ω    -27.00  30.00   0.50    0.05    --   47.70 -19.00-120.00  114
 32  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00  30.00   88
 33  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00  90.00   88
 34  ω     31.00  75.00   0.50    0.05    --  103.25 -61.00  60.00   88
 35  ω     31.00 111.00   0.50    0.05    --  103.25-125.00 -30.00  160
 36  ω     31.00 111.00   0.50    0.05    --  103.25-125.00 -90.00  160
 37  ω     31.00 111.00   0.50    0.05    --  103.25-125.00  60.00  160
 38  ω    -48.00 -23.00   0.50    0.05    --  -47.95  80.00  18.00   50
 39  ω     86.00 111.00   0.50    0.05    --  103.25-125.00   0.00   50
 40  ω    133.00 169.00   0.50    0.05    --  103.25  45.00-150.00   72
 41  ω    112.00 138.00   0.50    0.05    --  103.25  45.00-180.00   52
 42  ω     33.00  59.00   0.50    0.05    --  103.25-125.00   0.00   52
 43  ω   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00  60.00  172
 44  ω   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00 -90.00  172
 45  ω   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00-180.00  172
 46  ω     33.00 119.00   0.50    0.05    --   47.95  57.00-120.00  172
 47  ω     25.00 120.00   0.50    0.05    --   47.95  77.00 -60.00  190
 48  ω      0.00  25.00   0.50    0.05    --   47.95 -80.00-104.00   50
 49  ω     25.00 120.00   0.50    0.05    --   47.95  77.00 -30.00  190
 50  ω     36.00 121.00   0.50    0.05    --   47.95  37.00   0.00  170
 51  ω     25.00 110.00   0.50    0.05    --   47.95  77.00 120.00  170
 52  ω     25.00 120.00   0.50    0.05    --   47.95  77.00  90.00  190
 53  ω   -149.00-124.00   0.50    0.05    -- -101.00 -80.00-104.00   50
 54  ω   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00 120.00  172
 55  ω   -121.00 -35.00   0.50    0.05    --  -47.95 -37.00-150.00  172
 56  ω     36.00 121.00   0.50    0.05    --   47.95  37.00-120.00  170
 57  ω     25.00 120.00   0.50    0.05    --   47.95  77.00-180.00  190
 58  ω     33.00 119.00   0.50    0.05    --   47.95  57.00 -60.00  172
 59  ω    -26.00  30.00   0.50    0.05    --   47.95 -19.00 120.00  112
 60  ω     25.00 120.00   0.50    0.05    --   47.95  77.00-150.00  190
 61  ω     25.00  72.50   0.50    0.05    --   47.95  77.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1492120000
_diffrn_orient_matrix_UB_12      -0.0946661000
_diffrn_orient_matrix_UB_13      -0.0038630000
_diffrn_orient_matrix_UB_21      -0.0751169000
_diffrn_orient_matrix_UB_22      0.0878411000
_diffrn_orient_matrix_UB_23      0.0552654000
_diffrn_orient_matrix_UB_31      -0.0982541000
_diffrn_orient_matrix_UB_32      0.0766101000
_diffrn_orient_matrix_UB_33      -0.0681674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42427
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.091
_diffrn_reflns_theta_min         4.994
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0363
_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)+(0.0623P)²+0.1344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5715
_reflns_number_total             5845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00878_si_002.cif
_cod_data_source_block           chy_1
_cod_database_code               1566291
_shelx_shelxl_version_number     2018/3
_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_max   0.900
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
_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.a Ternary CH refined with riding coordinates:
 C31(H31), C12(H12), C13(H13), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B), C32(H32A,H32B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C8(H8)
2.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C40(H40A,H40B,H40C), C39(H39A,H39B,H39C), C43(H43A,H43B,
 H43C), C35(H35A,H35B,H35C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O41(H41), O38(H38)
;
_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.608
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
O19 O 0.1986(2) 0.15931(15) 0.90808(9) 0.0214(3) Uani 1 1 d . . . . .
O10 O 0.75090(18) 0.77923(15) 0.61688(8) 0.0190(3) Uani 1 1 d . . . . .
O37 O 0.3833(2) 0.00454(17) 0.72789(9) 0.0246(3) Uani 1 1 d . . . . .
O29 O 0.04651(19) 0.00094(16) 1.00390(9) 0.0226(3) Uani 1 1 d . . . . .
O41 O 0.2719(2) 0.56021(18) 0.68297(10) 0.0266(4) Uani 1 1 d . . . . .
H41 H 0.223037 0.608518 0.649459 0.040 Uiso 1 1 calc R U . . .
O42 O 0.23969(19) 0.74173(18) 0.58073(10) 0.0278(4) Uani 1 1 d . . . . .
O38 O 0.5176(2) 0.23241(18) 0.70851(9) 0.0255(4) Uani 1 1 d . . . . .
H38 H 0.498723 0.154412 0.701464 0.038 Uiso 1 1 calc R U . . .
O34 O -0.27056(19) -0.03267(17) 0.87717(10) 0.0273(4) Uani 1 1 d . . . . .
O11 O 0.7390(2) 1.04725(16) 0.57872(9) 0.0237(3) Uani 1 1 d . . . . .
O16 O 1.0090(2) 0.97228(18) 0.47111(10) 0.0282(4) Uani 1 1 d . . . . .
O36 O -0.0400(3) 0.14993(18) 1.07915(10) 0.0321(4) Uani 1 1 d . . . . .
O18 O 0.8914(2) 1.12671(19) 0.68610(10) 0.0336(4) Uani 1 1 d . . . . .
C3 C 0.3938(3) 0.7559(2) 0.59389(13) 0.0209(4) Uani 1 1 d . . . . .
C23 C 0.3604(3) 0.1855(2) 0.80727(12) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.4400(3) 0.5763(2) 0.68976(13) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.7208(3) 0.5118(2) 0.74782(12) 0.0196(4) Uani 1 1 d . . . . .
C27 C 0.3147(3) 0.3630(2) 0.89144(13) 0.0209(4) Uani 1 1 d . . . . .
H27 H 0.273440 0.392528 0.933724 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5042(3) 0.6714(2) 0.64556(12) 0.0191(4) Uani 1 1 d . . . . .
C22 C 0.3229(3) 0.0538(2) 0.78004(12) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.6525(3) 0.8256(2) 0.54505(12) 0.0191(4) Uani 1 1 d . . . . .
C9 C 0.6799(3) 0.6857(2) 0.65536(12) 0.0179(4) Uani 1 1 d . . . . .
C6 C 0.5458(3) 0.4978(2) 0.74142(12) 0.0204(4) Uani 1 1 d . . . . .
C24 C 0.4508(3) 0.2731(2) 0.76829(12) 0.0205(4) Uani 1 1 d . . . . .
C15 C 0.8832(3) 1.0587(2) 0.63064(13) 0.0242(5) Uani 1 1 d . . . . .
C28 C 0.2926(3) 0.2342(2) 0.86884(13) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.7867(3) 0.6077(2) 0.70532(12) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.902545 0.618531 0.710930 0.023 Uiso 1 1 calc R U . . .
C20 C 0.1967(3) 0.0183(2) 0.89808(12) 0.0199(4) Uani 1 1 d . . . . .
C33 C -0.0450(3) 0.1071(2) 1.01620(14) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.4763(3) 0.8644(2) 0.55750(13) 0.0221(4) Uani 1 1 d . . . . .
H2A H 0.484651 0.940957 0.589857 0.027 Uiso 1 1 calc R U . . .
H2B H 0.406960 0.886547 0.508836 0.027 Uiso 1 1 calc R U . . .
C25 C 0.4678(3) 0.4041(2) 0.78845(13) 0.0205(4) Uani 1 1 d . . . . .
C26 C 0.3989(3) 0.4482(2) 0.85081(13) 0.0218(5) Uani 1 1 d . . . . .
C31 C -0.1270(3) 0.0497(2) 0.88468(13) 0.0217(4) Uani 1 1 d . . . . .
H31 H -0.114288 0.087096 0.835513 0.026 Uiso 1 1 calc R U . . .
C44 C 0.6437(3) 0.7200(2) 0.48455(13) 0.0239(5) Uani 1 1 d . . . . .
H44A H 0.754779 0.687762 0.483768 0.036 Uiso 1 1 calc R U . . .
H44B H 0.596695 0.755756 0.435529 0.036 Uiso 1 1 calc R U . . .
H44C H 0.573938 0.649891 0.496184 0.036 Uiso 1 1 calc R U . . .
C40 C 0.3496(3) -0.0401(3) 0.94894(14) 0.0267(5) Uani 1 1 d . . . . .
H40A H 0.449725 -0.011137 0.932223 0.040 Uiso 1 1 calc R U . . .
H40B H 0.343246 -0.133486 0.946158 0.040 Uiso 1 1 calc R U . . .
H40C H 0.352644 -0.012745 1.000630 0.040 Uiso 1 1 calc R U . . .
C39 C 0.4147(3) 0.5900(2) 0.87329(15) 0.0279(5) Uani 1 1 d . . . . .
H39A H 0.345049 0.641665 0.835082 0.042 Uiso 1 1 calc R U . . .
H39B H 0.529803 0.616988 0.877718 0.042 Uiso 1 1 calc R U . . .
H39C H 0.379416 0.601724 0.921368 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7518(3) 0.9432(2) 0.52526(12) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.704938 0.972538 0.473438 0.025 Uiso 1 1 calc R U . . .
C21 C 0.1925(3) -0.0179(2) 0.81464(13) 0.0213(4) Uani 1 1 d . . . . .
H21A H 0.210943 -0.110894 0.811108 0.026 Uiso 1 1 calc R U . . .
H21B H 0.081789 0.001608 0.785473 0.026 Uiso 1 1 calc R U . . .
C43 C 0.8384(3) 0.4232(2) 0.79920(13) 0.0249(5) Uani 1 1 d . . . . .
H43A H 0.812271 0.425437 0.849549 0.037 Uiso 1 1 calc R U . . .
H43B H 0.952158 0.451610 0.801106 0.037 Uiso 1 1 calc R U . . .
H43C H 0.825901 0.335745 0.779801 0.037 Uiso 1 1 calc R U . . .
C13 C 0.9418(3) 0.9147(2) 0.53147(13) 0.0218(4) Uani 1 1 d . . . . .
H13 H 0.962462 0.820574 0.533375 0.026 Uiso 1 1 calc R U . . .
C32 C -0.1465(3) 0.1549(2) 0.94201(13) 0.0250(5) Uani 1 1 d . . . . .
H32A H -0.103494 0.237559 0.927465 0.030 Uiso 1 1 calc R U . . .
H32B H -0.263780 0.165687 0.946000 0.030 Uiso 1 1 calc R U . . .
C30 C 0.0336(3) -0.0239(2) 0.92274(12) 0.0203(4) Uani 1 1 d . . . . .
H30 H 0.017126 -0.117476 0.913277 0.024 Uiso 1 1 calc R U . . .
C14 C 1.0196(3) 0.9779(3) 0.60686(14) 0.0268(5) Uani 1 1 d . . . . .
H14A H 1.058718 0.911936 0.644915 0.032 Uiso 1 1 calc R U . . .
H14B H 1.114102 1.032400 0.600569 0.032 Uiso 1 1 calc R U . . .
C35 C -0.2765(3) -0.1260(3) 0.81748(16) 0.0320(5) Uani 1 1 d . . . . .
H35A H -0.267573 -0.082010 0.770885 0.048 Uiso 1 1 calc R U . . .
H35B H -0.381028 -0.172636 0.810938 0.048 Uiso 1 1 calc R U . . .
H35C H -0.184718 -0.186138 0.830436 0.048 Uiso 1 1 calc R U . . .
C17 C 1.0166(4) 0.8808(3) 0.41139(14) 0.0318(6) Uani 1 1 d . . . . .
H17A H 1.071373 0.920235 0.373712 0.048 Uiso 1 1 calc R U . . .
H17B H 0.904581 0.855350 0.388220 0.048 Uiso 1 1 calc R U . . .
H17C H 1.078820 0.805316 0.432149 0.048 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'
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
C28 O19 C20 119.44(17) . . ?
C9 O10 C1 117.32(16) . . ?
C33 O29 C30 111.09(17) . . ?
C5 O41 H41 109.5 . . ?
C24 O38 H38 109.5 . . ?
C31 O34 C35 112.58(18) . . ?
C15 O11 C12 110.95(17) . . ?
C13 O16 C17 111.50(19) . . ?
O42 C3 C4 122.3(2) . . ?
O42 C3 C2 121.1(2) . . ?
C4 C3 C2 116.58(19) . . ?
C24 C23 C22 121.42(19) . . ?
C28 C23 C22 120.4(2) . . ?
C28 C23 C24 117.9(2) . . ?
O41 C5 C4 120.07(19) . . ?
O41 C5 C6 118.26(19) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C7 C43 120.2(2) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 C43 119.5(2) . . ?
C28 C27 H27 120.1 . . ?
C28 C27 C26 119.9(2) . . ?
C26 C27 H27 120.1 . . ?
C5 C4 C3 121.48(19) . . ?
C9 C4 C3 120.5(2) . . ?
C9 C4 C5 117.99(19) . . ?
O37 C22 C23 123.1(2) . . ?
O37 C22 C21 120.8(2) . . ?
C23 C22 C21 115.90(19) . . ?
O10 C1 C2 109.19(16) . . ?
O10 C1 C44 109.75(18) . . ?
O10 C1 C12 103.65(17) . . ?
C44 C1 C2 111.28(19) . . ?
C44 C1 C12 110.92(17) . . ?
C12 C1 C2 111.76(18) . . ?
O10 C9 C4 121.26(19) . . ?
O10 C9 C8 117.48(19) . . ?
C8 C9 C4 121.3(2) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 C25 118.28(19) . . ?
C7 C6 C25 123.0(2) . . ?
O38 C24 C23 120.6(2) . . ?
O38 C24 C25 117.9(2) . . ?
C25 C24 C23 121.4(2) . . ?
O11 C15 C14 110.09(19) . . ?
O18 C15 O11 121.6(2) . . ?
O18 C15 C14 128.3(2) . . ?
O19 C28 C23 122.4(2) . . ?
O19 C28 C27 116.4(2) . . ?
C27 C28 C23 121.2(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
O19 C20 C40 109.27(18) . . ?
O19 C20 C21 110.97(17) . . ?
O19 C20 C30 103.66(17) . . ?
C40 C20 C21 110.90(19) . . ?
C40 C20 C30 111.60(18) . . ?
C30 C20 C21 110.24(17) . . ?
O29 C33 C32 110.18(19) . . ?
O36 C33 O29 121.3(2) . . ?
O36 C33 C32 128.5(2) . . ?
C3 C2 C1 111.57(18) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C24 C25 C6 120.6(2) . . ?
C24 C25 C26 118.7(2) . . ?
C26 C25 C6 120.5(2) . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 C39 119.6(2) . . ?
C25 C26 C39 119.6(2) . . ?
O34 C31 H31 111.5 . . ?
O34 C31 C32 107.60(18) . . ?
O34 C31 C30 110.89(18) . . ?
C32 C31 H31 111.5 . . ?
C32 C31 C30 103.57(18) . . ?
C30 C31 H31 111.5 . . ?
C1 C44 H44A 109.5 . . ?
C1 C44 H44B 109.5 . . ?
C1 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C20 C40 H40A 109.5 . . ?
C20 C40 H40B 109.5 . . ?
C20 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C26 C39 H39A 109.5 . . ?
C26 C39 H39B 109.5 . . ?
C26 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O11 C12 C1 109.03(17) . . ?
O11 C12 H12 109.4 . . ?
O11 C12 C13 106.39(17) . . ?
C1 C12 H12 109.4 . . ?
C1 C12 C13 113.07(18) . . ?
C13 C12 H12 109.4 . . ?
C22 C21 C20 112.85(18) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C7 C43 H43A 109.5 . . ?
C7 C43 H43B 109.5 . . ?
C7 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O16 C13 C12 112.35(18) . . ?
O16 C13 H13 110.4 . . ?
O16 C13 C14 109.83(19) . . ?
C12 C13 H13 110.4 . . ?
C14 C13 C12 103.11(18) . . ?
C14 C13 H13 110.4 . . ?
C33 C32 C31 104.68(19) . . ?
C33 C32 H32A 110.8 . . ?
C33 C32 H32B 110.8 . . ?
C31 C32 H32A 110.8 . . ?
C31 C32 H32B 110.8 . . ?
H32A C32 H32B 108.9 . . ?
O29 C30 C20 109.23(17) . . ?
O29 C30 C31 104.61(17) . . ?
O29 C30 H30 109.0 . . ?
C20 C30 C31 115.79(18) . . ?
C20 C30 H30 109.0 . . ?
C31 C30 H30 109.0 . . ?
C15 C14 C13 106.22(19) . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O34 C35 H35A 109.5 . . ?
O34 C35 H35B 109.5 . . ?
O34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O19 C28 1.361(3) . ?
O19 C20 1.458(3) . ?
O10 C1 1.458(2) . ?
O10 C9 1.366(3) . ?
O37 C22 1.236(3) . ?
O29 C33 1.357(3) . ?
O29 C30 1.455(3) . ?
O41 H41 0.8200 . ?
O41 C5 1.353(3) . ?
O42 C3 1.234(3) . ?
O38 H38 0.8200 . ?
O38 C24 1.347(3) . ?
O34 C31 1.422(3) . ?
O34 C35 1.426(3) . ?
O11 C15 1.355(3) . ?
O11 C12 1.448(3) . ?
O16 C13 1.421(3) . ?
O16 C17 1.430(3) . ?
O36 C33 1.200(3) . ?
O18 C15 1.202(3) . ?
C3 C4 1.448(3) . ?
C3 C2 1.505(3) . ?
C23 C22 1.449(3) . ?
C23 C24 1.418(3) . ?
C23 C28 1.407(3) . ?
C5 C4 1.412(3) . ?
C5 C6 1.393(3) . ?
C7 C6 1.406(3) . ?
C7 C8 1.406(3) . ?
C7 C43 1.501(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(3) . ?
C27 C26 1.391(3) . ?
C4 C9 1.407(3) . ?
C22 C21 1.508(3) . ?
C1 C2 1.535(3) . ?
C1 C44 1.522(3) . ?
C1 C12 1.526(3) . ?
C9 C8 1.378(3) . ?
C6 C25 1.490(3) . ?
C24 C25 1.392(3) . ?
C15 C14 1.501(3) . ?
C8 H8 0.9300 . ?
C20 C40 1.516(3) . ?
C20 C21 1.528(3) . ?
C20 C30 1.527(3) . ?
C33 C32 1.506(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C25 C26 1.407(3) . ?
C26 C39 1.509(3) . ?
C31 H31 0.9800 . ?
C31 C32 1.515(3) . ?
C31 C30 1.547(3) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C12 H12 0.9800 . ?
C12 C13 1.547(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.521(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C30 H30 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
O19 C20 C21 C22 48.9(2) . . . . ?
O19 C20 C30 O29 -66.2(2) . . . . ?
O19 C20 C30 C31 51.5(2) . . . . ?
O10 C1 C2 C3 -53.1(2) . . . . ?
O10 C1 C12 O11 -69.5(2) . . . . ?
O10 C1 C12 C13 48.6(2) . . . . ?
O10 C9 C8 C7 178.53(18) . . . . ?
O37 C22 C21 C20 151.0(2) . . . . ?
O29 C33 C32 C31 9.3(2) . . . . ?
O41 C5 C4 C3 1.7(3) . . . . ?
O41 C5 C4 C9 179.2(2) . . . . ?
O41 C5 C6 C7 178.7(2) . . . . ?
O41 C5 C6 C25 -2.4(3) . . . . ?
O42 C3 C4 C5 -6.6(3) . . . . ?
O42 C3 C4 C9 176.0(2) . . . . ?
O42 C3 C2 C1 -149.3(2) . . . . ?
O38 C24 C25 C6 4.7(3) . . . . ?
O38 C24 C25 C26 -179.95(19) . . . . ?
O34 C31 C32 C33 97.3(2) . . . . ?
O34 C31 C30 O29 -91.0(2) . . . . ?
O34 C31 C30 C20 148.73(18) . . . . ?
O11 C15 C14 C13 0.8(3) . . . . ?
O11 C12 C13 O16 -101.0(2) . . . . ?
O11 C12 C13 C14 17.2(2) . . . . ?
O16 C13 C14 C15 108.9(2) . . . . ?
O36 C33 C32 C31 -169.9(2) . . . . ?
O18 C15 C14 C13 -178.6(2) . . . . ?
C3 C4 C9 O10 0.2(3) . . . . ?
C3 C4 C9 C8 178.8(2) . . . . ?
C23 C22 C21 C20 -33.9(3) . . . . ?
C23 C24 C25 C6 -172.9(2) . . . . ?
C23 C24 C25 C26 2.5(3) . . . . ?
C5 C4 C9 O10 -177.28(19) . . . . ?
C5 C4 C9 C8 1.3(3) . . . . ?
C5 C6 C25 C24 99.6(3) . . . . ?
C5 C6 C25 C26 -75.7(3) . . . . ?
C7 C6 C25 C24 -81.5(3) . . . . ?
C7 C6 C25 C26 103.2(3) . . . . ?
C4 C3 C2 C1 31.7(3) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C4 C5 C6 C25 177.2(2) . . . . ?
C4 C9 C8 C7 -0.1(3) . . . . ?
C22 C23 C24 O38 -6.0(3) . . . . ?
C22 C23 C24 C25 171.5(2) . . . . ?
C22 C23 C28 O19 4.0(3) . . . . ?
C22 C23 C28 C27 -174.3(2) . . . . ?
C1 O10 C9 C4 -24.9(3) . . . . ?
C1 O10 C9 C8 156.38(19) . . . . ?
C1 C12 C13 O16 139.36(19) . . . . ?
C1 C12 C13 C14 -102.5(2) . . . . ?
C9 O10 C1 C2 50.9(2) . . . . ?
C9 O10 C1 C44 -71.3(2) . . . . ?
C9 O10 C1 C12 170.19(17) . . . . ?
C6 C5 C4 C3 -177.8(2) . . . . ?
C6 C5 C4 C9 -0.4(3) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C6 C25 C26 C27 175.1(2) . . . . ?
C6 C25 C26 C39 -4.2(3) . . . . ?
C24 C23 C22 O37 9.2(3) . . . . ?
C24 C23 C22 C21 -165.8(2) . . . . ?
C24 C23 C28 O19 177.50(19) . . . . ?
C24 C23 C28 C27 -0.8(3) . . . . ?
C24 C25 C26 C27 -0.3(3) . . . . ?
C24 C25 C26 C39 -179.5(2) . . . . ?
C15 O11 C12 C1 104.3(2) . . . . ?
C15 O11 C12 C13 -18.0(2) . . . . ?
C28 O19 C20 C40 82.8(2) . . . . ?
C28 O19 C20 C21 -39.8(3) . . . . ?
C28 O19 C20 C30 -158.07(17) . . . . ?
C28 C23 C22 O37 -177.6(2) . . . . ?
C28 C23 C22 C21 7.5(3) . . . . ?
C28 C23 C24 O38 -179.48(19) . . . . ?
C28 C23 C24 C25 -2.0(3) . . . . ?
C28 C27 C26 C25 -2.4(3) . . . . ?
C28 C27 C26 C39 176.8(2) . . . . ?
C8 C7 C6 C5 3.0(3) . . . . ?
C8 C7 C6 C25 -175.9(2) . . . . ?
C20 O19 C28 C23 13.6(3) . . . . ?
C20 O19 C28 C27 -168.04(19) . . . . ?
C33 O29 C30 C20 104.9(2) . . . . ?
C33 O29 C30 C31 -19.7(2) . . . . ?
C2 C3 C4 C5 172.4(2) . . . . ?
C2 C3 C4 C9 -5.0(3) . . . . ?
C2 C1 C12 O11 47.9(2) . . . . ?
C2 C1 C12 C13 166.07(18) . . . . ?
C26 C27 C28 O19 -175.4(2) . . . . ?
C26 C27 C28 C23 3.0(3) . . . . ?
C44 C1 C2 C3 68.2(2) . . . . ?
C44 C1 C12 O11 172.77(17) . . . . ?
C44 C1 C12 C13 -69.1(2) . . . . ?
C40 C20 C21 C22 -72.7(2) . . . . ?
C40 C20 C30 O29 51.3(2) . . . . ?
C40 C20 C30 C31 169.0(2) . . . . ?
C12 O11 C15 O18 -169.6(2) . . . . ?
C12 O11 C15 C14 10.9(3) . . . . ?
C12 C1 C2 C3 -167.14(18) . . . . ?
C12 C13 C14 C15 -11.0(2) . . . . ?
C21 C20 C30 O29 174.99(18) . . . . ?
C21 C20 C30 C31 -67.3(2) . . . . ?
C43 C7 C6 C5 -176.1(2) . . . . ?
C43 C7 C6 C25 5.0(3) . . . . ?
C43 C7 C8 C9 177.0(2) . . . . ?
C32 C31 C30 O29 24.2(2) . . . . ?
C32 C31 C30 C20 -96.1(2) . . . . ?
C30 O29 C33 O36 -173.9(2) . . . . ?
C30 O29 C33 C32 6.8(2) . . . . ?
C30 C20 C21 C22 163.17(19) . . . . ?
C30 C31 C32 C33 -20.2(2) . . . . ?
C35 O34 C31 C32 172.6(2) . . . . ?
C35 O34 C31 C30 -74.8(2) . . . . ?
C17 O16 C13 C12 -97.3(2) . . . . ?
C17 O16 C13 C14 148.6(2) . . . . ?
