#------------------------------------------------------------------------------
#$Date: 2020-07-21 02:05:15 +0300 (Tue, 21 Jul 2020) $
#$Revision: 254409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558623.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_1558623
loop_
_publ_author_name
'Zhang, Jian'
'Liu, Zhi-Wen'
'Li, Yong'
'Wei, Cui-Jie'
'Xie, Jing'
'Yuan, Meng-Fei'
'Zhang, Dong-Mei'
'Ye, Wen-Cai'
'Zhang, Xiao-Qi'
_publ_section_title
;
 Structurally Diverse Indole Alkaloids with Vasorelaxant Activity from
 Melodinus hemsleyanus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00925
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_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     dual
_audit_creation_date             2019-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6535(3)
_cell_length_b                   13.7374(5)
_cell_length_c                   31.5932(15)
_cell_measurement_reflns_used    6630
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4480
_cell_measurement_theta_min      3.4710
_cell_volume                     3321.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -33.00  65.00   1.00    1.10    --   40.98 -37.00  30.00   98
  2  ω      0.00 121.00   1.00    1.10    --   40.98  19.00-150.00  121
  3  ω     94.00 178.00   1.00    4.39    --  106.95 125.00   0.00   84
  4  ω     24.00 109.00   1.00    4.39    --  106.95 -94.00 -60.00   85
  5  ω     24.00 109.00   1.00    4.39    --  106.95 -94.00   0.00   85
  6  ω     94.00 178.00   1.00    4.39    --  106.95 125.00 -30.00   84
  7  ω     81.00 178.00   1.00    4.39    --  106.95  45.00 -60.00   97
  8  ω     79.00 178.00   1.00    4.39    --  106.95  30.00  60.00   99
  9  ω     94.00 178.00   1.00    4.39    --  106.95 125.00  90.00   84
 10  ω   -117.00  -8.00   1.00    1.10    --  -40.98 -77.00  30.00  109
 11  ω      1.00  82.00   1.00    1.10    --   40.98 -99.00-120.00   81
 12  ω     79.00 134.00   1.00    4.39    --  106.95  30.00-150.00   55
;
_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      0.1131659000
_diffrn_orient_matrix_UB_12      0.0806102000
_diffrn_orient_matrix_UB_13      -0.0199570000
_diffrn_orient_matrix_UB_21      0.0591801000
_diffrn_orient_matrix_UB_22      0.0324036000
_diffrn_orient_matrix_UB_23      0.0444333000
_diffrn_orient_matrix_UB_31      0.1555924000
_diffrn_orient_matrix_UB_32      -0.0709061000
_diffrn_orient_matrix_UB_33      -0.0023907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.785
_diffrn_reflns_theta_min         2.797
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.00040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0951
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0492P)²+13.7136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2350
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5963
_reflns_number_total             6612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b00925_si_002.cif
_cod_data_source_block           dnh-a-15
_cod_database_code               1558623
_shelx_shelxl_version_number     2016/4
_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   0.923
_shelx_estimated_absorpt_t_min   0.910
_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, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00I), C00S(H00S), C00Z(H00Z), C014(H014)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00Q(H00C,H00D), C00V(H00E,H00F), C00W(H00G,H00H), C015(H01D,
 H01E), C017(H01F,H01G), C01B(H01I,H01J), C01D(H01L,H01M)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00H(H00J), C00N(H00N), C00R(H00R), C00U(H00U),
 C00X(H00X), C00Y(H00Y), C010(H010), C013(H013), C016(H016), C018(H018),
 C01A(H01H), C01C(H01K)
2.d Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C01E(H01N,H01O,H01P)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.483
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
O001 O 0.0928(4) 1.1257(2) 0.29661(10) 0.0323(7) Uani 1 1 d . . . . .
O002 O 0.6948(4) 0.8569(2) 0.33550(10) 0.0361(8) Uani 1 1 d . . . . .
O003 O 1.1299(4) 0.4065(2) 0.44465(10) 0.0390(8) Uani 1 1 d . . . . .
O004 O 0.6066(4) 0.7353(2) 0.43463(10) 0.0398(8) Uani 1 1 d . . . . .
O005 O -0.1874(4) 1.0967(2) 0.28229(12) 0.0482(10) Uani 1 1 d . . . . .
N006 N 0.3869(4) 1.1420(2) 0.27307(12) 0.0306(9) Uani 1 1 d . . . . .
N007 N 0.4536(5) 0.8706(2) 0.37582(12) 0.0308(9) Uani 1 1 d . . . . .
H007 H 0.490119 0.824123 0.391774 0.037 Uiso 1 1 calc R . . . .
N008 N 0.8372(5) 0.7183(2) 0.39131(12) 0.0335(9) Uani 1 1 d . . . . .
H008 H 0.801784 0.767767 0.377004 0.040 Uiso 1 1 calc R . . . .
O009 O 1.1756(6) 0.2929(2) 0.39546(13) 0.0601(11) Uani 1 1 d . . . . .
N00A N 0.9758(5) 0.4752(3) 0.50255(13) 0.0396(10) Uani 1 1 d . . . . .
C00B C 0.7424(6) 0.6917(3) 0.42474(14) 0.0321(10) Uani 1 1 d . . . . .
C00C C 0.5507(5) 0.8939(3) 0.34204(14) 0.0287(10) Uani 1 1 d . . . . .
C00D C 0.2431(6) 1.0026(3) 0.36674(14) 0.0296(10) Uani 1 1 d . . . . .
C00E C -0.0400(5) 1.0686(3) 0.28332(15) 0.0330(10) Uani 1 1 d . . . . .
C00F C 0.8010(6) 0.6028(3) 0.44837(14) 0.0327(10) Uani 1 1 d . . . . .
H00I H 0.769700 0.610542 0.478260 0.039 Uiso 1 1 calc R . . . .
C00G C 0.4582(6) 1.1357(3) 0.34527(14) 0.0333(11) Uani 1 1 d . . . . .
H00A H 0.576972 1.118387 0.352884 0.040 Uiso 1 1 calc R . . . .
H00B H 0.402843 1.166683 0.369379 0.040 Uiso 1 1 calc R . . . .
C00H C 1.0572(6) 0.6961(3) 0.33825(16) 0.0360(11) Uani 1 1 d . . . . .
H00J H 0.999888 0.742537 0.321926 0.043 Uiso 1 1 calc R . . . .
C00I C 0.2967(5) 0.9166(3) 0.38705(14) 0.0300(10) Uani 1 1 d . . . . .
C00J C 0.2612(5) 1.0777(3) 0.29053(14) 0.0286(10) Uani 1 1 d . . . . .
C00K C 0.9921(6) 0.6714(3) 0.37751(15) 0.0318(11) Uani 1 1 d . . . . .
C00L C 0.2249(5) 0.9891(3) 0.26263(15) 0.0309(10) Uani 1 1 d . . . . .
C00M C 0.9813(5) 0.4685(3) 0.45904(15) 0.0314(10) Uani 1 1 d . . . . .
C00N C 0.3004(5) 1.0983(3) 0.20279(15) 0.0338(11) Uani 1 1 d . . . . .
H00N H 0.303634 1.109110 0.173739 0.041 Uiso 1 1 calc R . . . .
C00O C 1.0720(5) 0.6012(3) 0.40280(15) 0.0312(10) Uani 1 1 d . . . . .
C00P C 0.3545(5) 1.0445(3) 0.33149(14) 0.0293(10) Uani 1 1 d . . . . .
C00Q C 0.3517(6) 1.1796(3) 0.23198(15) 0.0364(11) Uani 1 1 d . . . . .
H00C H 0.454826 1.212051 0.221075 0.044 Uiso 1 1 calc R . . . .
H00D H 0.257885 1.226930 0.233544 0.044 Uiso 1 1 calc R . . . .
C00R C 0.0984(6) 1.0495(3) 0.38290(15) 0.0365(11) Uani 1 1 d . . . . .
H00R H 0.064464 1.108589 0.371131 0.044 Uiso 1 1 calc R . . . .
C00S C 0.4718(5) 0.9643(3) 0.31161(14) 0.0281(10) Uani 1 1 d . . . . .
H00S H 0.566274 0.996035 0.295862 0.034 Uiso 1 1 calc R . . . .
C00T C 1.0761(7) 0.3506(3) 0.41139(16) 0.0440(13) Uani 1 1 d . . . . .
C00U C 0.2504(5) 1.0113(3) 0.21696(15) 0.0340(11) Uani 1 1 d . . . . .
H00U H 0.230554 0.962059 0.197342 0.041 Uiso 1 1 calc R . . . .
C00V C 0.4565(6) 1.2040(3) 0.30641(15) 0.0353(11) Uani 1 1 d . . . . .
H00E H 0.381866 1.260001 0.311234 0.042 Uiso 1 1 calc R . . . .
H00F H 0.573416 1.226368 0.299575 0.042 Uiso 1 1 calc R . . . .
C00W C 0.3528(5) 0.9106(3) 0.27976(14) 0.0318(10) Uani 1 1 d . . . . .
H00G H 0.289156 0.858583 0.293685 0.038 Uiso 1 1 calc R . . . .
H00H H 0.421398 0.883002 0.256902 0.038 Uiso 1 1 calc R . . . .
C00X C 0.2019(6) 0.8777(3) 0.42066(15) 0.0382(12) Uani 1 1 d . . . . .
H00X H 0.238202 0.820040 0.433360 0.046 Uiso 1 1 calc R . . . .
C00Y C 1.2061(6) 0.6527(3) 0.32314(17) 0.0416(12) Uani 1 1 d . . . . .
H00Y H 1.249085 0.668587 0.296480 0.050 Uiso 1 1 calc R . . . .
C00Z C 0.0297(5) 0.9688(3) 0.27238(15) 0.0347(11) Uani 1 1 d . . . . .
H00Z H 0.025506 0.929581 0.298277 0.042 Uiso 1 1 calc R . . . .
C010 C 0.0545(6) 0.9246(3) 0.43506(16) 0.0424(12) Uani 1 1 d . . . . .
H010 H -0.009529 0.898421 0.457347 0.051 Uiso 1 1 calc R . . . .
C011 C 0.9971(6) 0.5777(3) 0.44556(14) 0.0344(11) Uani 1 1 d . . . . .
C012 C -0.0786(6) 0.9162(3) 0.23928(17) 0.0429(13) Uani 1 1 d . . . . .
H01A H -0.194942 0.906520 0.249829 0.064 Uiso 1 1 calc GR . . . .
H01B H -0.026357 0.854260 0.233157 0.064 Uiso 1 1 calc GR . . . .
H01C H -0.083026 0.954592 0.213909 0.064 Uiso 1 1 calc GR . . . .
C013 C 1.2271(6) 0.5619(3) 0.38729(18) 0.0431(13) Uani 1 1 d . . . . .
H013 H 1.289367 0.518399 0.404071 0.052 Uiso 1 1 calc R . . . .
C014 C 0.8940(7) 0.3771(3) 0.39843(16) 0.0425(13) Uani 1 1 d . . . . .
H014 H 0.904026 0.428523 0.377066 0.051 Uiso 1 1 calc R . . . .
C015 C 0.7007(6) 0.5136(3) 0.43036(17) 0.0406(12) Uani 1 1 d . . . . .
H01D H 0.589105 0.505783 0.444531 0.049 Uiso 1 1 calc R . . . .
H01E H 0.680149 0.521294 0.400245 0.049 Uiso 1 1 calc R . . . .
C016 C 0.0015(7) 1.0112(3) 0.41620(17) 0.0442(13) Uani 1 1 d . . . . .
H016 H -0.097954 1.043248 0.425792 0.053 Uiso 1 1 calc R . . . .
C017 C 1.1072(7) 0.6220(3) 0.48188(15) 0.0452(13) Uani 1 1 d . . . . .
H01F H 1.224831 0.636383 0.472336 0.054 Uiso 1 1 calc R . . . .
H01G H 1.054056 0.681421 0.492324 0.054 Uiso 1 1 calc R . . . .
C018 C 1.2909(6) 0.5855(4) 0.34790(18) 0.0483(14) Uani 1 1 d . . . . .
H018 H 1.392018 0.555687 0.337977 0.058 Uiso 1 1 calc R . . . .
C019 C 0.8205(6) 0.4252(3) 0.43896(16) 0.0391(12) Uani 1 1 d . . . . .
C01A C 0.7410(8) 0.3505(3) 0.46811(19) 0.0525(15) Uani 1 1 d . . . . .
H01H H 0.645406 0.315190 0.458376 0.063 Uiso 1 1 calc R . . . .
C01B C 1.1093(8) 0.5429(4) 0.51663(16) 0.0512(15) Uani 1 1 d . . . . .
H01I H 1.222590 0.511491 0.518297 0.061 Uiso 1 1 calc R . . . .
H01J H 1.080409 0.570205 0.544067 0.061 Uiso 1 1 calc R . . . .
C01C C 0.7985(9) 0.3324(3) 0.50626(19) 0.0572(16) Uani 1 1 d . . . . .
H01K H 0.746238 0.282244 0.521433 0.069 Uiso 1 1 calc R . . . .
C01D C 0.9419(10) 0.3872(4) 0.52667(17) 0.0603(17) Uani 1 1 d . . . . .
H01L H 0.909527 0.403900 0.555449 0.072 Uiso 1 1 calc R . . . .
H01M H 1.046467 0.347327 0.527679 0.072 Uiso 1 1 calc R . . . .
C01E C 0.7942(9) 0.2944(4) 0.3782(2) 0.0622(18) Uani 1 1 d . . . . .
H01N H 0.855176 0.272727 0.353400 0.093 Uiso 1 1 calc GR . . . .
H01O H 0.679569 0.316413 0.370477 0.093 Uiso 1 1 calc GR . . . .
H01P H 0.784593 0.241565 0.397967 0.093 Uiso 1 1 calc GR . . . .
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
C00E O001 C00J 111.2(3) . . ?
C00T O003 C00M 109.1(4) . . ?
C00J N006 C00Q 116.9(3) . . ?
C00J N006 C00V 109.4(3) . . ?
C00Q N006 C00V 121.1(3) . . ?
C00C N007 H007 117.7 . . ?
C00C N007 C00I 124.7(3) . . ?
C00I N007 H007 117.7 . . ?
C00B N008 H008 117.5 . . ?
C00B N008 C00K 125.0(4) . . ?
C00K N008 H008 117.5 . . ?
C00M N00A C01B 109.1(4) . . ?
C00M N00A C01D 118.2(4) . . ?
C01B N00A C01D 119.9(4) . . ?
O004 C00B N008 121.6(4) . . ?
O004 C00B C00F 121.2(4) . . ?
N008 C00B C00F 117.1(4) . . ?
O002 C00C N007 122.1(4) . . ?
O002 C00C C00S 121.5(4) . . ?
N007 C00C C00S 116.4(4) . . ?
C00I C00D C00P 119.4(4) . . ?
C00R C00D C00I 117.2(4) . . ?
C00R C00D C00P 123.1(4) . . ?
O001 C00E C00Z 109.4(3) . . ?
O005 C00E O001 122.2(4) . . ?
O005 C00E C00Z 128.4(4) . . ?
C00B C00F H00I 108.5 . . ?
C00B C00F C011 116.4(4) . . ?
C00B C00F C015 108.2(4) . . ?
C011 C00F H00I 108.5 . . ?
C011 C00F C015 106.5(3) . . ?
C015 C00F H00I 108.5 . . ?
H00A C00G H00B 108.8 . . ?
C00P C00G H00A 110.7 . . ?
C00P C00G H00B 110.7 . . ?
C00P C00G C00V 105.3(4) . . ?
C00V C00G H00A 110.7 . . ?
C00V C00G H00B 110.7 . . ?
C00K C00H H00J 119.8 . . ?
C00Y C00H H00J 119.8 . . ?
C00Y C00H C00K 120.4(4) . . ?
N007 C00I C00D 120.9(4) . . ?
C00X C00I N007 117.8(4) . . ?
C00X C00I C00D 121.3(4) . . ?
O001 C00J C00L 105.9(3) . . ?
O001 C00J C00P 115.5(3) . . ?
N006 C00J O001 111.7(3) . . ?
N006 C00J C00L 113.3(4) . . ?
N006 C00J C00P 101.3(3) . . ?
C00L C00J C00P 109.4(3) . . ?
C00H C00K N008 117.8(4) . . ?
C00H C00K C00O 121.9(4) . . ?
C00O C00K N008 120.3(4) . . ?
C00J C00L C00W 103.7(3) . . ?
C00J C00L C00Z 101.8(3) . . ?
C00U C00L C00J 111.8(3) . . ?
C00U C00L C00W 113.4(3) . . ?
C00U C00L C00Z 110.9(4) . . ?
C00Z C00L C00W 114.4(3) . . ?
O003 C00M C011 114.0(3) . . ?
O003 C00M C019 105.6(3) . . ?
N00A C00M O003 111.4(3) . . ?
N00A C00M C011 102.1(3) . . ?
N00A C00M C019 114.9(4) . . ?
C019 C00M C011 109.1(4) . . ?
C00Q C00N H00N 118.8 . . ?
C00U C00N H00N 118.8 . . ?
C00U C00N C00Q 122.4(4) . . ?
C00K C00O C011 119.8(4) . . ?
C013 C00O C00K 116.1(4) . . ?
C013 C00O C011 123.9(4) . . ?
C00D C00P C00G 112.9(4) . . ?
C00D C00P C00J 117.8(3) . . ?
C00D C00P C00S 110.6(3) . . ?
C00G C00P C00J 103.5(3) . . ?
C00G C00P C00S 113.1(3) . . ?
C00J C00P C00S 97.9(3) . . ?
N006 C00Q C00N 109.9(3) . . ?
N006 C00Q H00C 109.7 . . ?
N006 C00Q H00D 109.7 . . ?
C00N C00Q H00C 109.7 . . ?
C00N C00Q H00D 109.7 . . ?
H00C C00Q H00D 108.2 . . ?
C00D C00R H00R 118.9 . . ?
C00D C00R C016 122.1(4) . . ?
C016 C00R H00R 118.9 . . ?
C00C C00S C00P 115.7(4) . . ?
C00C C00S H00S 108.5 . . ?
C00C C00S C00W 110.4(3) . . ?
C00P C00S H00S 108.5 . . ?
C00W C00S C00P 105.2(3) . . ?
C00W C00S H00S 108.5 . . ?
O003 C00T C014 110.7(4) . . ?
O009 C00T O003 120.0(5) . . ?
O009 C00T C014 129.2(5) . . ?
C00L C00U H00U 118.4 . . ?
C00N C00U C00L 123.2(4) . . ?
C00N C00U H00U 118.4 . . ?
N006 C00V C00G 102.8(3) . . ?
N006 C00V H00E 111.2 . . ?
N006 C00V H00F 111.2 . . ?
C00G C00V H00E 111.2 . . ?
C00G C00V H00F 111.2 . . ?
H00E C00V H00F 109.1 . . ?
C00L C00W H00G 110.7 . . ?
C00L C00W H00H 110.7 . . ?
C00S C00W C00L 105.4(3) . . ?
C00S C00W H00G 110.7 . . ?
C00S C00W H00H 110.7 . . ?
H00G C00W H00H 108.8 . . ?
C00I C00X H00X 120.0 . . ?
C010 C00X C00I 119.9(4) . . ?
C010 C00X H00X 120.0 . . ?
C00H C00Y H00Y 120.4 . . ?
C00H C00Y C018 119.1(5) . . ?
C018 C00Y H00Y 120.4 . . ?
C00E C00Z C00L 102.8(3) . . ?
C00E C00Z H00Z 107.2 . . ?
C00E C00Z C012 113.4(4) . . ?
C00L C00Z H00Z 107.2 . . ?
C012 C00Z C00L 118.4(4) . . ?
C012 C00Z H00Z 107.2 . . ?
C00X C010 H010 120.1 . . ?
C00X C010 C016 119.8(4) . . ?
C016 C010 H010 120.1 . . ?
C00F C011 C00M 97.1(3) . . ?
C00F C011 C017 113.5(4) . . ?
C00O C011 C00F 112.0(4) . . ?
C00O C011 C00M 118.7(3) . . ?
C00O C011 C017 112.0(4) . . ?
C017 C011 C00M 102.5(3) . . ?
C00Z C012 H01A 109.5 . . ?
C00Z C012 H01B 109.5 . . ?
C00Z C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
C00O C013 H013 119.0 . . ?
C018 C013 C00O 122.0(4) . . ?
C018 C013 H013 119.0 . . ?
C00T C014 H014 106.9 . . ?
C00T C014 C019 102.5(4) . . ?
C00T C014 C01E 113.8(4) . . ?
C019 C014 H014 106.9 . . ?
C01E C014 H014 106.9 . . ?
C01E C014 C019 119.2(5) . . ?
C00F C015 H01D 110.7 . . ?
C00F C015 H01E 110.7 . . ?
H01D C015 H01E 108.8 . . ?
C019 C015 C00F 105.2(4) . . ?
C019 C015 H01D 110.7 . . ?
C019 C015 H01E 110.7 . . ?
C00R C016 C010 119.5(4) . . ?
C00R C016 H016 120.3 . . ?
C010 C016 H016 120.3 . . ?
C011 C017 H01F 110.8 . . ?
C011 C017 H01G 110.8 . . ?
H01F C017 H01G 108.9 . . ?
C01B C017 C011 104.8(4) . . ?
C01B C017 H01F 110.8 . . ?
C01B C017 H01G 110.8 . . ?
C00Y C018 C013 120.4(5) . . ?
C00Y C018 H018 119.8 . . ?
C013 C018 H018 119.8 . . ?
C00M C019 C014 102.7(4) . . ?
C00M C019 C015 104.4(3) . . ?
C015 C019 C014 113.9(4) . . ?
C01A C019 C00M 110.0(4) . . ?
C01A C019 C014 111.2(4) . . ?
C01A C019 C015 113.8(4) . . ?
C019 C01A H01H 118.1 . . ?
C01C C01A C019 123.8(5) . . ?
C01C C01A H01H 118.1 . . ?
N00A C01B C017 103.0(4) . . ?
N00A C01B H01I 111.2 . . ?
N00A C01B H01J 111.2 . . ?
C017 C01B H01I 111.2 . . ?
C017 C01B H01J 111.2 . . ?
H01I C01B H01J 109.1 . . ?
C01A C01C H01K 118.1 . . ?
C01A C01C C01D 123.8(5) . . ?
C01D C01C H01K 118.1 . . ?
N00A C01D C01C 109.1(5) . . ?
N00A C01D H01L 109.9 . . ?
N00A C01D H01M 109.9 . . ?
C01C C01D H01L 109.9 . . ?
C01C C01D H01M 109.9 . . ?
H01L C01D H01M 108.3 . . ?
C014 C01E H01N 109.5 . . ?
C014 C01E H01O 109.5 . . ?
C014 C01E H01P 109.5 . . ?
H01N C01E H01O 109.5 . . ?
H01N C01E H01P 109.5 . . ?
H01O C01E H01P 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 C00E 1.350(5) . ?
O001 C00J 1.460(5) . ?
O002 C00C 1.232(5) . ?
O003 C00M 1.492(5) . ?
O003 C00T 1.365(6) . ?
O004 C00B 1.240(5) . ?
O005 C00E 1.193(5) . ?
N006 C00J 1.417(5) . ?
N006 C00Q 1.423(6) . ?
N006 C00V 1.456(6) . ?
N007 H007 0.8600 . ?
N007 C00C 1.339(6) . ?
N007 C00I 1.403(5) . ?
N008 H008 0.8600 . ?
N008 C00B 1.333(6) . ?
N008 C00K 1.418(6) . ?
O009 C00T 1.209(6) . ?
N00A C00M 1.378(6) . ?
N00A C01B 1.451(7) . ?
N00A C01D 1.453(6) . ?
C00B C00F 1.500(6) . ?
C00C C00S 1.492(6) . ?
C00D C00I 1.406(5) . ?
C00D C00P 1.516(6) . ?
C00D C00R 1.379(6) . ?
C00E C00Z 1.512(6) . ?
C00F H00I 0.9800 . ?
C00F C011 1.542(6) . ?
C00F C015 1.554(6) . ?
C00G H00A 0.9700 . ?
C00G H00B 0.9700 . ?
C00G C00P 1.545(6) . ?
C00G C00V 1.546(6) . ?
C00H H00J 0.9300 . ?
C00H C00K 1.380(7) . ?
C00H C00Y 1.372(6) . ?
C00I C00X 1.392(6) . ?
C00J C00L 1.529(6) . ?
C00J C00P 1.547(6) . ?
C00K C00O 1.394(6) . ?
C00L C00U 1.488(7) . ?
C00L C00W 1.554(6) . ?
C00L C00Z 1.551(6) . ?
C00M C011 1.563(5) . ?
C00M C019 1.508(6) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.500(6) . ?
C00N C00U 1.333(6) . ?
C00O C011 1.502(6) . ?
C00O C013 1.393(6) . ?
C00P C00S 1.554(6) . ?
C00Q H00C 0.9700 . ?
C00Q H00D 0.9700 . ?
C00R H00R 0.9300 . ?
C00R C016 1.390(7) . ?
C00S H00S 0.9800 . ?
C00S C00W 1.545(6) . ?
C00T C014 1.498(8) . ?
C00U H00U 0.9300 . ?
C00V H00E 0.9700 . ?
C00V H00F 0.9700 . ?
C00W H00G 0.9700 . ?
C00W H00H 0.9700 . ?
C00X H00X 0.9300 . ?
C00X C010 1.377(7) . ?
C00Y H00Y 0.9300 . ?
C00Y C018 1.373(7) . ?
C00Z H00Z 0.9800 . ?
C00Z C012 1.517(6) . ?
C010 H010 0.9300 . ?
C010 C016 1.391(7) . ?
C011 C017 1.548(7) . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 0.9600 . ?
C013 H013 0.9300 . ?
C013 C018 1.376(8) . ?
C014 H014 0.9800 . ?
C014 C019 1.547(7) . ?
C014 C01E 1.510(7) . ?
C015 H01D 0.9700 . ?
C015 H01E 0.9700 . ?
C015 C019 1.546(6) . ?
C016 H016 0.9300 . ?
C017 H01F 0.9700 . ?
C017 H01G 0.9700 . ?
C017 C01B 1.544(7) . ?
C018 H018 0.9300 . ?
C019 C01A 1.507(7) . ?
C01A H01H 0.9300 . ?
C01A C01C 1.307(8) . ?
C01B H01I 0.9700 . ?
C01B H01J 0.9700 . ?
C01C H01K 0.9300 . ?
C01C C01D 1.479(9) . ?
C01D H01L 0.9700 . ?
C01D H01M 0.9700 . ?
C01E H01N 0.9600 . ?
C01E H01O 0.9600 . ?
C01E H01P 0.9600 . ?
