#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:09:44 +0300 (Fri, 05 May 2023) $
#$Revision: 283430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159181.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_7159181
loop_
_publ_author_name
'Jiang, Yaqin'
'Chen, Chunmei'
'Zhu, Hucheng'
'Li, Qin'
'Mao, Lina'
'Liao, Hong'
'Nan, Yiyang'
'Wang, Zhiping'
'Zhou, Hongjian'
'Zhou, Qun'
'Zhang, Yonghui'
_publ_section_title
;
 An indole diketopiperazine alkaloid and a bisabolane sesquiterpenoid with
 unprecedented skeletons from Aspergillus fumigatus.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2236
_journal_page_last               2242
_journal_paper_doi               10.1039/d2ob02220f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H33 N3 O5'
_chemical_formula_sum            'C27 H33 N3 O5'
_chemical_formula_weight         479.56
_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             2022-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9746(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.57868(7)
_cell_length_b                   5.12531(3)
_cell_length_c                   17.35284(9)
_cell_measurement_reflns_used    23365
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8700
_cell_measurement_theta_min      3.2830
_cell_volume                     1195.991(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     90.00 117.00   0.50    0.50    --   32.00  72.00 122.12   54
  2  ω      6.00  41.00   0.50    0.50    --   32.00  72.00 122.12   70
  3  ω    -54.00  -3.00   0.50    0.50    --   32.00 -43.00-121.06  102
  4  ω      3.00  50.00   0.50    0.50    --   32.00 -43.00-121.06   94
  5  ω     15.00  42.00   0.50    0.50    --   40.00  72.00 -63.25   54
  6  ω     14.00  58.00   0.50    0.50    --   40.00  70.00-137.82   88
  7  ω     98.00 123.00   0.50    0.50    --   40.00  70.00-137.82   50
  8  ω     32.00  57.00   0.50    0.50    --   60.00  75.00 101.37   50
  9  ω     32.00  66.00   0.50    0.50    --   60.00  75.00  18.82   68
 10  ω     32.00  59.00   0.50    0.50    --   60.00  75.00 -19.23   54
 11  ω     32.00  58.00   0.50    0.50    --   60.00  74.00  56.13   52
 12  ω     39.00  83.00   0.50    0.50    --   60.00  73.00 -60.35   88
 13  ω     36.00  73.00   0.50    0.50    --   64.00  75.00 127.51   74
 14  ω     87.00 143.00   0.50    0.50    --   64.00  75.00 127.51  112
 15  ω     44.00  69.00   0.50    0.50    --   68.00  68.00  74.12   50
 16  ω     40.00  65.00   0.50    0.50    --   68.00  75.00 -92.86   50
 17  ω    112.00 156.00   0.50    0.50    --   68.00  75.00 -92.86   88
 18  ω    129.00 161.00   0.50    0.50    --   72.00  74.00 131.15   64
 19  ω     52.00  78.00   0.50    0.50    --   72.00  50.00  13.98   52
 20  ω     45.00  73.00   0.50    0.50    --   72.00  73.00-120.63   56
 21  ω     44.00  70.00   0.50    0.50    --   72.00  74.00 131.15   52
 22  ω    108.00 161.00   0.50    0.50    --   72.00  73.00-120.63  106
 23  ω     44.00  70.00   0.50    0.50    --   72.00  75.00-145.78   52
 24  ω     48.00  99.00   0.50    0.50    --   76.00  75.00 170.40  102
 25  ω    112.00 139.00   0.50    0.50    --   76.00  75.00 170.40   54
 26  ω     48.00  93.00   0.50    0.50    --   76.00  74.00 149.25   90
 27  ω    138.00 164.00   0.50    0.50    --   76.00  74.00 149.25   52
 28  ω    125.00 165.00   0.50    0.50    --   80.00  66.00 -67.43   80
 29  ω     55.00  81.00   0.50    0.50    --   80.00  66.00 -67.43   52
 30  ω     55.00  81.00   0.50    0.50    --   80.00  69.00  94.77   52
 31  ω     57.00  92.00   0.50    0.50    --   84.00  75.00-148.88   70
 32  ω     64.00 125.00   0.50    0.50    --   95.20 -82.00 -90.00  122
 33  ω      6.00  43.00   0.50    0.50    --   95.20 -82.00 -90.00   74
 34  ω     73.00 104.00   0.50    0.50    --   95.20  62.00  52.22   62
 35  ω     96.00 126.00   0.50    0.50    --   95.20 -82.00-150.00   60
 36  ω     76.00 180.00   0.50    0.50    --   95.20  61.00  90.00  208
 37  ω    120.00 153.00   0.50    0.50    --   95.20  61.00-180.00   66
 38  ω     62.00  93.00   0.50    0.50    --   95.20 -82.00-150.00   62
 39  ω     56.00 126.00   0.50    0.50    --   95.20 -82.00  60.00  140
 40  ω     27.00  63.00   0.50    0.50    --   95.20 -45.00 -30.00   72
 41  ω     11.00  52.00   0.50    0.50    --   95.20 -82.00  60.00   82
 42  ω     67.00 117.00   0.50    0.50    --   95.20 -61.00-180.00  100
 43  ω     29.00  55.00   0.50    0.50    --   95.20 -61.00-180.00   52
 44  ω     76.00 156.00   0.50    0.50    --   95.20  45.00-120.00  160
 45  ω     72.00 175.00   0.50    0.50    --   95.20  61.00   0.00  206
 46  ω     74.00 126.00   0.50    0.50    --   95.20  57.00 -71.69  104
 47  ω    140.00 185.00   0.50    0.50    --   95.20  61.00 -60.00   90
 48  ω     73.00 130.00   0.50    0.50    --   95.20  61.00 -60.00  114
 49  ω     68.00 180.00   0.50    0.50    --   95.20  71.00 104.20  224
 50  ω    123.00 184.00   0.50    0.50    --   95.20  68.00-114.62  122
 51  ω     72.00 108.00   0.50    0.50    --   95.20  68.00-114.62   72
 52  ω     73.00 112.00   0.50    0.50    --   95.20 -45.00 -30.00   78
 53  ω     69.00 145.00   0.50    0.50    --   95.20  70.00  19.03  152
 54  ω     76.00 113.00   0.50    0.50    --   95.20  61.00-180.00   74
 55  ω     72.00 116.00   0.50    0.50    --   95.20  61.00 -30.00   88
 56  ω     97.00 183.00   0.50    0.50    --   95.20  77.00 150.00  172
 57  ω     72.00 146.00   0.50    0.50    --   95.20  71.00  54.80  148
 58  ω     23.00 116.00   0.50    0.50    --   95.20 -61.00 120.00  186
 59  ω     75.00 105.00   0.50    0.50    --   95.20  58.00 144.90   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0517297000
_diffrn_orient_matrix_UB_12      -0.0463820000
_diffrn_orient_matrix_UB_13      -0.0836458000
_diffrn_orient_matrix_UB_21      0.1012570000
_diffrn_orient_matrix_UB_22      0.0163885000
_diffrn_orient_matrix_UB_23      -0.0302170000
_diffrn_orient_matrix_UB_31      0.0137188000
_diffrn_orient_matrix_UB_32      -0.2965254000
_diffrn_orient_matrix_UB_33      0.0114505000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25692
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.171
_diffrn_reflns_theta_min         2.571
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0084(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0271
_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)+(0.0390P)²+0.3549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                4688
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02220f2.cif
_cod_data_source_block           20220628_jyq1-41-1
_cod_depositor_comments          'Adding full bibliography for 7159181.cif.'
_cod_original_cell_volume        1195.992(11)
_cod_database_code               7159181
_shelx_shelxl_version_number     2019/2
_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.
;
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.729
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C00E(H00E), C00H(H00H), C00K(H00K), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00O(H00D,H00F), C00Q(H00G,H00I), C00U(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00C(H00C), C00J(H00J), C00P(H00P), C00R(H00R)
2.d X=CH2 refined with riding coordinates:
 C00W(H00T,H00U)
2.e Idealised Me refined as rotating group:
 C00V(H00N,H00O,H00Q), C00X(H00V,H00W,H00X), C00Y(H00Y,H,HA), C00Z(H00Z,HB,HC)
2.f Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_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 1.829
_oxdiff_exptl_absorpt_empirical_full_min 0.486
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
O001 O 0.06006(8) 0.1001(2) 0.44382(7) 0.0150(3) Uani 1 1 d . . . . .
H001 H 0.000740 0.065715 0.433333 0.023 Uiso 1 1 calc R U . . .
O002 O 0.37994(8) 0.0303(2) 0.40904(7) 0.0153(3) Uani 1 1 d . . . . .
O003 O 0.20245(8) 0.7033(2) 0.44834(7) 0.0149(3) Uani 1 1 d . . . . .
H003 H 0.152771 0.791608 0.451367 0.022 Uiso 1 1 calc R U . . .
O004 O 0.12944(9) 0.4402(3) 0.58674(7) 0.0180(3) Uani 1 1 d . . . . .
O005 O 0.57373(10) 1.0484(3) 0.18942(7) 0.0217(3) Uani 1 1 d . . . . .
N006 N 0.24405(10) 0.2815(3) 0.41645(7) 0.0118(3) Uani 1 1 d . . . . .
N007 N 0.28209(10) 0.2801(3) 0.57631(8) 0.0136(3) Uani 1 1 d . . . . .
N008 N 0.32079(10) 0.5867(3) 0.30430(8) 0.0140(3) Uani 1 1 d . . . . .
H008 H 0.319576 0.668104 0.347502 0.017 Uiso 1 1 calc R U . . .
C009 C 0.33010(11) 0.1654(3) 0.44701(9) 0.0124(3) Uani 1 1 d . . . . .
C00A C 0.19519(12) 0.3813(3) 0.54701(9) 0.0129(3) Uani 1 1 d . . . . .
C00B C 0.37972(12) 0.6500(4) 0.24883(9) 0.0141(3) Uani 1 1 d . . . . .
C00C C 0.45128(12) 0.8451(4) 0.24908(10) 0.0154(3) Uani 1 1 d . . . . .
H00C H 0.464746 0.961352 0.290350 0.019 Uiso 1 1 calc R U . . .
C00D C 0.26351(12) 0.3705(4) 0.27949(9) 0.0133(3) Uani 1 1 d . . . . .
C00E C 0.19916(11) 0.2466(4) 0.33360(9) 0.0132(3) Uani 1 1 d . . . . .
H00E H 0.192181 0.059905 0.321961 0.016 Uiso 1 1 calc R U . . .
C00F C 0.50152(12) 0.8575(4) 0.18468(10) 0.0173(4) Uani 1 1 d . . . . .
C00G C 0.35686(12) 0.4732(4) 0.18644(10) 0.0145(3) Uani 1 1 d . . . . .
C00H C 0.07762(12) 0.3592(3) 0.41897(9) 0.0123(3) Uani 1 1 d . . . . .
H00H H 0.025896 0.481068 0.430277 0.015 Uiso 1 1 calc R U . . .
C00I C 0.28213(12) 0.2964(4) 0.20702(9) 0.0142(3) Uani 1 1 d . . . . .
C00J C 0.48005(13) 0.6860(4) 0.12136(10) 0.0193(4) Uani 1 1 d . . . . .
H00J H 0.514547 0.700318 0.078845 0.023 Uiso 1 1 calc R U . . .
C00K C 0.36469(11) 0.2244(3) 0.53223(9) 0.0135(3) Uani 1 1 d . . . . .
H00K H 0.407739 0.378542 0.535031 0.016 Uiso 1 1 calc R U . . .
C00L C 0.00810(12) 0.2534(4) 0.27921(10) 0.0180(4) Uani 1 1 d . . . . .
C00M C 0.18054(12) 0.4359(3) 0.45969(9) 0.0121(3) Uani 1 1 d . . . . .
C00N C 0.30791(12) 0.1925(4) 0.65701(10) 0.0162(4) Uani 1 1 d . . . . .
H00A H 0.248895 0.158288 0.681112 0.019 Uiso 1 1 calc R U . . .
H00B H 0.349015 0.319763 0.687889 0.019 Uiso 1 1 calc R U . . .
C00O C 0.42276(14) 0.0023(4) 0.57825(10) 0.0204(4) Uani 1 1 d . . . . .
H00D H 0.425291 -0.150766 0.545721 0.025 Uiso 1 1 calc R U . . .
H00F H 0.490204 0.056962 0.597092 0.025 Uiso 1 1 calc R U . . .
C00P C 0.40771(13) 0.4958(4) 0.12203(10) 0.0173(4) Uani 1 1 d . . . . .
H00P H 0.393055 0.383673 0.079854 0.021 Uiso 1 1 calc R U . . .
C00Q C 0.23832(12) 0.0806(4) 0.15502(9) 0.0160(3) Uani 1 1 d . . . . .
H00G H 0.205776 -0.043236 0.185418 0.019 Uiso 1 1 calc R U . . .
H00I H 0.291317 -0.010510 0.134042 0.019 Uiso 1 1 calc R U . . .
C00R C 0.16404(13) 0.1797(4) 0.08872(11) 0.0217(4) Uani 1 1 d . . . . .
H00R H 0.117149 0.298797 0.101380 0.026 Uiso 1 1 calc R U . . .
C00S C 0.09425(12) 0.3691(4) 0.33300(9) 0.0140(3) Uani 1 1 d . . . . .
H00S H 0.099123 0.553321 0.318932 0.017 Uiso 1 1 calc R U . . .
C00T C 0.15868(14) 0.1147(4) 0.01425(10) 0.0231(4) Uani 1 1 d . . . . .
C00U C 0.36523(14) -0.0569(4) 0.64682(10) 0.0214(4) Uani 1 1 d . . . . .
H00L H 0.320265 -0.202874 0.634761 0.026 Uiso 1 1 calc R U . . .
H00M H 0.410562 -0.096995 0.693575 0.026 Uiso 1 1 calc R U . . .
C00V C -0.08861(13) 0.3966(5) 0.28023(12) 0.0257(4) Uani 1 1 d . . . . .
H00N H -0.114686 0.357264 0.327576 0.039 Uiso 1 1 calc R U . . .
H00O H -0.135417 0.342762 0.236528 0.039 Uiso 1 1 calc R U . . .
H00Q H -0.077356 0.581023 0.277251 0.039 Uiso 1 1 calc R U . . .
C00W C 0.01305(14) 0.0442(5) 0.23571(11) 0.0258(4) Uani 1 1 d . . . . .
H00T H -0.043759 -0.017276 0.204972 0.031 Uiso 1 1 calc R U . . .
H00U H 0.073360 -0.041822 0.235766 0.031 Uiso 1 1 calc R U . . .
C00X C 0.62914(17) 1.0763(5) 0.12694(13) 0.0348(5) Uani 1 1 d . . . . .
H00V H 0.584961 1.114114 0.080153 0.052 Uiso 1 1 calc R U . . .
H00W H 0.664297 0.917118 0.120329 0.052 Uiso 1 1 calc R U . . .
H00X H 0.675873 1.216474 0.137815 0.052 Uiso 1 1 calc R U . . .
C00Y C 0.08436(19) 0.2357(6) -0.04773(13) 0.0416(6) Uani 1 1 d . . . . .
H00Y H 0.042638 0.101876 -0.073541 0.062 Uiso 1 1 calc R U . . .
H H 0.118789 0.323746 -0.084886 0.062 Uiso 1 1 calc R U . . .
HA H 0.044170 0.358766 -0.024353 0.062 Uiso 1 1 calc R U . . .
C00Z C 0.2276(2) -0.0737(6) -0.01633(13) 0.0470(7) Uani 1 1 d . . . . .
H00Z H 0.275111 -0.136264 0.025783 0.071 Uiso 1 1 calc R U . . .
HB H 0.261929 0.011975 -0.054007 0.071 Uiso 1 1 calc R U . . .
HC H 0.190220 -0.218093 -0.040439 0.071 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'
N N 0.0311 0.0180 '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
C00H O001 H001 109.5 . . ?
C00M O003 H003 109.5 . . ?
C00F O005 C00X 118.46(15) . . ?
C009 N006 C00E 122.70(13) . . ?
C009 N006 C00M 125.41(13) . . ?
C00M N006 C00E 111.74(12) . . ?
C00A N007 C00K 125.42(14) . . ?
C00A N007 C00N 124.67(14) . . ?
C00N N007 C00K 109.81(13) . . ?
C00B N008 H008 125.5 . . ?
C00B N008 C00D 109.10(14) . . ?
C00D N008 H008 125.5 . . ?
O002 C009 N006 123.41(15) . . ?
O002 C009 C00K 121.20(14) . . ?
N006 C009 C00K 115.33(14) . . ?
O004 C00A N007 123.68(15) . . ?
O004 C00A C00M 120.19(15) . . ?
N007 C00A C00M 116.07(14) . . ?
N008 C00B C00C 129.87(16) . . ?
N008 C00B C00G 107.35(15) . . ?
C00C C00B C00G 122.77(15) . . ?
C00B C00C H00C 121.6 . . ?
C00F C00C C00B 116.77(16) . . ?
C00F C00C H00C 121.6 . . ?
N008 C00D C00E 119.41(14) . . ?
C00I C00D N008 109.83(15) . . ?
C00I C00D C00E 130.63(16) . . ?
N006 C00E C00D 110.78(13) . . ?
N006 C00E H00E 109.3 . . ?
N006 C00E C00S 102.09(12) . . ?
C00D C00E H00E 109.3 . . ?
C00D C00E C00S 115.80(14) . . ?
C00S C00E H00E 109.3 . . ?
O005 C00F C00C 114.13(16) . . ?
O005 C00F C00J 123.97(15) . . ?
C00C C00F C00J 121.90(16) . . ?
C00B C00G C00I 107.50(14) . . ?
C00P C00G C00B 118.64(16) . . ?
C00P C00G C00I 133.85(17) . . ?
O001 C00H H00H 112.2 . . ?
O001 C00H C00M 106.28(13) . . ?
O001 C00H C00S 112.12(14) . . ?
C00M C00H H00H 112.2 . . ?
C00M C00H C00S 101.07(12) . . ?
C00S C00H H00H 112.2 . . ?
C00D C00I C00G 106.19(16) . . ?
C00D C00I C00Q 130.49(16) . . ?
C00G C00I C00Q 123.32(15) . . ?
C00F C00J H00J 119.9 . . ?
C00P C00J C00F 120.26(16) . . ?
C00P C00J H00J 119.9 . . ?
N007 C00K C009 112.96(13) . . ?
N007 C00K H00K 108.1 . . ?
N007 C00K C00O 104.24(13) . . ?
C009 C00K H00K 108.1 . . ?
C009 C00K C00O 115.09(14) . . ?
C00O C00K H00K 108.1 . . ?
C00V C00L C00S 113.75(17) . . ?
C00W C00L C00S 125.13(17) . . ?
C00W C00L C00V 121.10(17) . . ?
O003 C00M N006 107.62(13) . . ?
O003 C00M C00A 108.26(14) . . ?
O003 C00M C00H 112.31(13) . . ?
N006 C00M C00A 114.06(14) . . ?
N006 C00M C00H 101.03(13) . . ?
C00A C00M C00H 113.39(13) . . ?
N007 C00N H00A 111.4 . . ?
N007 C00N H00B 111.4 . . ?
N007 C00N C00U 101.82(14) . . ?
H00A C00N H00B 109.3 . . ?
C00U C00N H00A 111.4 . . ?
C00U C00N H00B 111.4 . . ?
C00K C00O H00D 110.6 . . ?
C00K C00O H00F 110.6 . . ?
H00D C00O H00F 108.8 . . ?
C00U C00O C00K 105.51(14) . . ?
C00U C00O H00D 110.6 . . ?
C00U C00O H00F 110.6 . . ?
C00G C00P H00P 120.2 . . ?
C00J C00P C00G 119.64(17) . . ?
C00J C00P H00P 120.2 . . ?
C00I C00Q H00G 109.2 . . ?
C00I C00Q H00I 109.2 . . ?
C00I C00Q C00R 112.22(16) . . ?
H00G C00Q H00I 107.9 . . ?
C00R C00Q H00G 109.2 . . ?
C00R C00Q H00I 109.2 . . ?
C00Q C00R H00R 116.6 . . ?
C00T C00R C00Q 126.76(18) . . ?
C00T C00R H00R 116.6 . . ?
C00E C00S H00S 107.3 . . ?
C00H C00S C00E 103.74(12) . . ?
C00H C00S H00S 107.3 . . ?
C00L C00S C00E 118.38(15) . . ?
C00L C00S C00H 112.34(13) . . ?
C00L C00S H00S 107.3 . . ?
C00R C00T C00Y 122.3(2) . . ?
C00R C00T C00Z 123.80(18) . . ?
C00Z C00T C00Y 113.86(19) . . ?
C00N C00U C00O 104.28(15) . . ?
C00N C00U H00L 110.9 . . ?
C00N C00U H00M 110.9 . . ?
C00O C00U H00L 110.9 . . ?
C00O C00U H00M 110.9 . . ?
H00L C00U H00M 108.9 . . ?
C00L C00V H00N 109.5 . . ?
C00L C00V H00O 109.5 . . ?
C00L C00V H00Q 109.5 . . ?
H00N C00V H00O 109.5 . . ?
H00N C00V H00Q 109.5 . . ?
H00O C00V H00Q 109.5 . . ?
C00L C00W H00T 120.0 . . ?
C00L C00W H00U 120.0 . . ?
H00T C00W H00U 120.0 . . ?
O005 C00X H00V 109.5 . . ?
O005 C00X H00W 109.5 . . ?
O005 C00X H00X 109.5 . . ?
H00V C00X H00W 109.5 . . ?
H00V C00X H00X 109.5 . . ?
H00W C00X H00X 109.5 . . ?
C00T C00Y H00Y 109.5 . . ?
C00T C00Y H 109.5 . . ?
C00T C00Y HA 109.5 . . ?
H00Y C00Y H 109.5 . . ?
H00Y C00Y HA 109.5 . . ?
H C00Y HA 109.5 . . ?
C00T C00Z H00Z 109.5 . . ?
C00T C00Z HB 109.5 . . ?
C00T C00Z HC 109.5 . . ?
H00Z C00Z HB 109.5 . . ?
H00Z C00Z HC 109.5 . . ?
HB C00Z HC 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
O001 H001 0.8200 . ?
O001 C00H 1.426(2) . ?
O002 C009 1.223(2) . ?
O003 H003 0.8200 . ?
O003 C00M 1.422(2) . ?
O004 C00A 1.239(2) . ?
O005 C00F 1.380(2) . ?
O005 C00X 1.410(2) . ?
N006 C009 1.352(2) . ?
N006 C00E 1.4924(19) . ?
N006 C00M 1.453(2) . ?
N007 C00A 1.324(2) . ?
N007 C00K 1.470(2) . ?
N007 C00N 1.466(2) . ?
N008 H008 0.8600 . ?
N008 C00B 1.373(2) . ?
N008 C00D 1.388(2) . ?
C009 C00K 1.519(2) . ?
C00A C00M 1.527(2) . ?
C00B C00C 1.394(3) . ?
C00B C00G 1.413(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.389(2) . ?
C00D C00E 1.509(2) . ?
C00D C00I 1.370(2) . ?
C00E H00E 0.9800 . ?
C00E C00S 1.555(2) . ?
C00F C00J 1.406(3) . ?
C00G C00I 1.442(2) . ?
C00G C00P 1.398(2) . ?
C00H H00H 0.9800 . ?
C00H C00M 1.527(2) . ?
C00H C00S 1.540(2) . ?
C00I C00Q 1.498(2) . ?
C00J H00J 0.9300 . ?
C00J C00P 1.385(3) . ?
C00K H00K 0.9800 . ?
C00K C00O 1.543(2) . ?
C00L C00S 1.512(2) . ?
C00L C00V 1.507(3) . ?
C00L C00W 1.318(3) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00N C00U 1.520(3) . ?
C00O H00D 0.9700 . ?
C00O H00F 0.9700 . ?
C00O C00U 1.541(3) . ?
C00P H00P 0.9300 . ?
C00Q H00G 0.9700 . ?
C00Q H00I 0.9700 . ?
C00Q C00R 1.509(2) . ?
C00R H00R 0.9300 . ?
C00R C00T 1.327(3) . ?
C00S H00S 0.9800 . ?
C00T C00Y 1.503(3) . ?
C00T C00Z 1.493(3) . ?
C00U H00L 0.9700 . ?
C00U H00M 0.9700 . ?
C00V H00N 0.9600 . ?
C00V H00O 0.9600 . ?
C00V H00Q 0.9600 . ?
C00W H00T 0.9300 . ?
C00W H00U 0.9300 . ?
C00X H00V 0.9600 . ?
C00X H00W 0.9600 . ?
C00X H00X 0.9600 . ?
C00Y H00Y 0.9600 . ?
C00Y H 0.9600 . ?
C00Y HA 0.9600 . ?
C00Z H00Z 0.9600 . ?
C00Z HB 0.9600 . ?
C00Z HC 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
O001 C00H C00M O003 -172.14(13) . . . . ?
O001 C00H C00M N006 73.46(14) . . . . ?
O001 C00H C00M C00A -49.02(17) . . . . ?
O001 C00H C00S C00E -72.17(16) . . . . ?
O001 C00H C00S C00L 56.84(19) . . . . ?
O002 C009 C00K N007 -153.88(16) . . . . ?
O002 C009 C00K C00O -34.3(2) . . . . ?
O004 C00A C00M O003 80.55(19) . . . . ?
O004 C00A C00M N006 -159.69(15) . . . . ?
O004 C00A C00M C00H -44.8(2) . . . . ?
O005 C00F C00J C00P 178.56(17) . . . . ?
N006 C009 C00K N007 29.0(2) . . . . ?
N006 C009 C00K C00O 148.51(15) . . . . ?
N006 C00E C00S C00H -21.52(16) . . . . ?
N006 C00E C00S C00L -146.75(15) . . . . ?
N007 C00A C00M O003 -96.78(17) . . . . ?
N007 C00A C00M N006 23.0(2) . . . . ?
N007 C00A C00M C00H 137.90(15) . . . . ?
N007 C00K C00O C00U 1.08(18) . . . . ?
N007 C00N C00U C00O 35.88(17) . . . . ?
N008 C00B C00C C00F 178.26(16) . . . . ?
N008 C00B C00G C00I -0.83(19) . . . . ?
N008 C00B C00G C00P -179.70(15) . . . . ?
N008 C00D C00E N006 -30.0(2) . . . . ?
N008 C00D C00E C00S 85.58(18) . . . . ?
N008 C00D C00I C00G 1.33(18) . . . . ?
N008 C00D C00I C00Q -178.63(16) . . . . ?
C009 N006 C00E C00D -67.1(2) . . . . ?
C009 N006 C00E C00S 169.02(15) . . . . ?
C009 N006 C00M O003 98.68(18) . . . . ?
C009 N006 C00M C00A -21.4(2) . . . . ?
C009 N006 C00M C00H -143.44(15) . . . . ?
C009 C00K C00O C00U -123.19(15) . . . . ?
C00A N007 C00K C009 -28.3(2) . . . . ?
C00A N007 C00K C00O -153.92(16) . . . . ?
C00A N007 C00N C00U 139.47(17) . . . . ?
C00B N008 C00D C00E 174.35(14) . . . . ?
C00B N008 C00D C00I -1.91(19) . . . . ?
C00B C00C C00F O005 -177.88(15) . . . . ?
C00B C00C C00F C00J 1.4(3) . . . . ?
C00B C00G C00I C00D -0.30(19) . . . . ?
C00B C00G C00I C00Q 179.66(15) . . . . ?
C00B C00G C00P C00J 1.2(3) . . . . ?
C00C C00B C00G C00I 178.47(15) . . . . ?
C00C C00B C00G C00P -0.4(3) . . . . ?
C00C C00F C00J C00P -0.6(3) . . . . ?
C00D N008 C00B C00C -177.58(17) . . . . ?
C00D N008 C00B C00G 1.66(18) . . . . ?
C00D C00E C00S C00H -141.95(14) . . . . ?
C00D C00E C00S C00L 92.82(19) . . . . ?
C00D C00I C00Q C00R 104.1(2) . . . . ?
C00E N006 C009 O002 2.6(3) . . . . ?
C00E N006 C009 C00K 179.73(15) . . . . ?
C00E N006 C00M O003 -85.81(16) . . . . ?
C00E N006 C00M C00A 154.07(14) . . . . ?
C00E N006 C00M C00H 32.07(17) . . . . ?
C00E C00D C00I C00G -174.38(16) . . . . ?
C00E C00D C00I C00Q 5.7(3) . . . . ?
C00F C00J C00P C00G -0.7(3) . . . . ?
C00G C00B C00C C00F -0.9(2) . . . . ?
C00G C00I C00Q C00R -75.8(2) . . . . ?
C00I C00D C00E N006 145.33(17) . . . . ?
C00I C00D C00E C00S -99.1(2) . . . . ?
C00I C00G C00P C00J -177.30(18) . . . . ?
C00I C00Q C00R C00T 133.4(2) . . . . ?
C00K N007 C00A O004 -175.49(17) . . . . ?
C00K N007 C00A C00M 1.7(2) . . . . ?
C00K N007 C00N C00U -37.24(18) . . . . ?
C00K C00O C00U C00N -22.99(18) . . . . ?
C00M N006 C009 O002 177.68(16) . . . . ?
C00M N006 C009 C00K -5.2(2) . . . . ?
C00M N006 C00E C00D 117.23(15) . . . . ?
C00M N006 C00E C00S -6.64(18) . . . . ?
C00M C00H C00S C00E 40.66(16) . . . . ?
C00M C00H C00S C00L 169.67(15) . . . . ?
C00N N007 C00A O004 8.3(3) . . . . ?
C00N N007 C00A C00M -174.46(16) . . . . ?
C00N N007 C00K C009 148.39(15) . . . . ?
C00N N007 C00K C00O 22.76(18) . . . . ?
C00P C00G C00I C00D 178.32(18) . . . . ?
C00P C00G C00I C00Q -1.7(3) . . . . ?
C00Q C00R C00T C00Y -177.0(2) . . . . ?
C00Q C00R C00T C00Z 0.2(4) . . . . ?
C00S C00H C00M O003 70.68(16) . . . . ?
C00S C00H C00M N006 -43.73(15) . . . . ?
C00S C00H C00M C00A -166.20(14) . . . . ?
C00V C00L C00S C00E -176.78(15) . . . . ?
C00V C00L C00S C00H 62.3(2) . . . . ?
C00W C00L C00S C00E 4.6(3) . . . . ?
C00W C00L C00S C00H -116.3(2) . . . . ?
C00X O005 C00F C00C 179.83(18) . . . . ?
C00X O005 C00F C00J 0.6(3) . . . . ?
