#------------------------------------------------------------------------------
#$Date: 2020-08-05 01:43:03 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/51/4135127.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_4135127
loop_
_publ_author_name
'Andres, Rémi'
'Wang, Qian'
'Zhu, Jieping'
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Arborisidine and
 (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective
 Pictet-Spengler Reaction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c05804
_journal_year                    2020
_chemical_formula_sum            'C27 H32 N2 O3'
_chemical_formula_weight         432.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                105.663(6)
_cell_angle_beta                 98.138(9)
_cell_angle_gamma                105.425(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1818(13)
_cell_length_b                   9.8124(7)
_cell_length_c                   14.8937(9)
_cell_measurement_reflns_used    2437
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      3.1610
_cell_volume                     1212.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury 4.1.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.956
_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  -9.00   1.00    9.06    --  -40.41 -77.00   0.00  107
  2  ω   -115.00 -25.00   1.00    9.06    --  -40.41 -38.00-120.00   90
  3  ω     25.00  90.00   1.00    9.06    --   40.41-125.00-120.00   65
  4  ω      2.00  30.00   1.00    9.06    --   40.41 -99.00-120.00   28
  5  ω      1.00  66.00   1.00    9.06    --   40.41 -99.00 120.00   65
  6  ω     88.00 115.00   1.00    9.06    --   40.41  38.00  30.00   27
  7  ω    101.00 172.00   1.00   36.24    --  107.03 125.00   0.00   71
  8  ω     93.00 169.00   1.00   36.24    --  107.03  30.00   0.00   76
  9  ω     88.00 178.00   1.00   36.24    --  107.03  45.00  60.00   90
 10  ω     79.00 118.00   1.00   36.24    --  107.03-125.00  60.00   39
 11  ω     34.00 131.00   1.00   36.24    --  107.03 -77.00  60.00   97
 12  ω     39.00 118.00   1.00   36.24    --  107.03-125.00-120.00   79
 13  ω     76.00 134.00   1.00   36.24    --  107.03 -30.00-180.00   58
 14  ω    102.00 129.00   1.00   36.24    --  107.03 125.00 -90.00   27
 15  ω     34.00  97.00   1.00   36.24    --  107.03 -94.00 -60.00   63
 16  ω     38.00 134.00   1.00   36.24    --  107.03 -30.00  30.00   96
 17  ω     59.00 134.00   1.00   36.24    --  107.03 -61.00 -90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8111
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.831
_diffrn_reflns_theta_min         3.166
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       irregular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0038(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0520
_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)+(0.0790P)²+0.0302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3506
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c05804_si_004.cif
_cod_data_source_block           rat27
_cod_database_code               4135127
_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_min   0.848
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6390(2) 0.7814(2) 0.07954(12) 0.0579(4) Uani 1 1 d . . . . .
O2 O 0.71074(17) 0.49089(15) 0.04661(9) 0.0437(3) Uani 1 1 d . . . . .
O3 O 0.83773(16) 0.48162(15) 0.18534(9) 0.0416(3) Uani 1 1 d . . . . .
N1 N 0.60830(19) 0.85756(18) 0.30845(10) 0.0399(4) Uani 1 1 d . . . . .
N2 N 0.40050(18) 0.46854(17) 0.14246(11) 0.0373(4) Uani 1 1 d . . . . .
H2 H 0.378(3) 0.465(3) 0.0867(19) 0.041(6) Uiso 1 1 d . . . . .
C1 C 0.5282(3) 0.8331(3) 0.38484(14) 0.0509(5) Uani 1 1 d . . . . .
H1A H 0.417(3) 0.836(3) 0.3715(17) 0.044(6) Uiso 1 1 d . . . . .
H1B H 0.586(3) 0.921(3) 0.447(2) 0.058(7) Uiso 1 1 d . . . . .
C2 C 0.5251(3) 0.6843(3) 0.39829(14) 0.0534(5) Uani 1 1 d . . . . .
H2A H 0.629(3) 0.688(3) 0.430(2) 0.060(7) Uiso 1 1 d . . . . .
H2B H 0.454(4) 0.660(4) 0.438(2) 0.077(9) Uiso 1 1 d . . . . .
C3 C 0.4638(2) 0.5645(2) 0.30324(13) 0.0432(4) Uani 1 1 d . . . . .
C4 C 0.3942(2) 0.4057(2) 0.27740(15) 0.0436(4) Uani 1 1 d . . . . .
C5 C 0.3561(3) 0.3058(3) 0.32896(18) 0.0549(6) Uani 1 1 d . . . . .
H5 H 0.377(3) 0.342(3) 0.396(2) 0.048(6) Uiso 1 1 d . . . . .
C6 C 0.2837(3) 0.1562(3) 0.2792(2) 0.0578(6) Uani 1 1 d . . . . .
H6 H 0.253(4) 0.085(4) 0.315(2) 0.077(9) Uiso 1 1 d . . . . .
C7 C 0.2492(2) 0.1032(3) 0.17921(19) 0.0510(5) Uani 1 1 d . . . . .
H7 H 0.202(3) -0.003(3) 0.147(2) 0.058(7) Uiso 1 1 d . . . . .
C8 C 0.2840(2) 0.1979(2) 0.12591(16) 0.0447(5) Uani 1 1 d . . . . .
H8 H 0.259(3) 0.162(3) 0.0518(17) 0.043(6) Uiso 1 1 d . . . . .
C9 C 0.3560(2) 0.3498(2) 0.17612(14) 0.0396(4) Uani 1 1 d . . . . .
C10 C 0.4655(2) 0.5984(2) 0.22020(12) 0.0363(4) Uani 1 1 d . . . . .
C11 C 0.5238(2) 0.7508(2) 0.21168(12) 0.0367(4) Uani 1 1 d . . . . .
C12 C 0.3912(2) 0.7917(2) 0.16212(14) 0.0440(5) Uani 1 1 d . . . . .
H12A H 0.334(3) 0.708(3) 0.1010(18) 0.047(6) Uiso 1 1 d . . . . .
H12B H 0.315(3) 0.796(3) 0.202(2) 0.060(8) Uiso 1 1 d . . . . .
H12C H 0.434(3) 0.891(3) 0.1452(19) 0.056(7) Uiso 1 1 d . . . . .
C13 C 0.6489(2) 0.7490(2) 0.15233(13) 0.0386(4) Uani 1 1 d . . . . .
C14 C 0.7852(2) 0.7033(2) 0.19075(14) 0.0400(4) Uani 1 1 d . . . . .
H14 H 0.784(3) 0.707(3) 0.2564(18) 0.042(6) Uiso 1 1 d . . . . .
C15 C 0.9373(3) 0.8076(3) 0.1842(2) 0.0665(7) Uani 1 1 d . . . . .
H15A H 1.022(4) 0.776(3) 0.216(2) 0.075(9) Uiso 1 1 d . . . . .
H15B H 0.947(4) 0.912(4) 0.223(2) 0.070(8) Uiso 1 1 d . . . . .
H15C H 0.936(5) 0.796(4) 0.109(3) 0.106(13) Uiso 1 1 d . . . . .
C16 C 0.7699(2) 0.5455(2) 0.13101(13) 0.0365(4) Uani 1 1 d . . . . .
C17 C 0.8535(2) 0.3309(2) 0.14424(13) 0.0432(5) Uani 1 1 d . . . . .
C18 C 0.6946(3) 0.2151(3) 0.10786(17) 0.0504(5) Uani 1 1 d . . . . .
H18A H 0.704(3) 0.115(3) 0.0900(19) 0.054(7) Uiso 1 1 d . . . . .
H18B H 0.628(3) 0.230(3) 0.0536(19) 0.052(7) Uiso 1 1 d . . . . .
H18C H 0.636(3) 0.218(3) 0.157(2) 0.060(8) Uiso 1 1 d . . . . .
C19 C 0.9479(3) 0.3351(3) 0.06800(15) 0.0518(5) Uani 1 1 d . . . . .
H19A H 0.889(3) 0.344(3) 0.009(2) 0.054(7) Uiso 1 1 d . . . . .
H19B H 1.051(4) 0.419(4) 0.092(3) 0.085(10) Uiso 1 1 d . . . . .
H19C H 0.960(4) 0.234(4) 0.047(2) 0.074(9) Uiso 1 1 d . . . . .
C20 C 0.9464(3) 0.3135(3) 0.23088(17) 0.0559(6) Uani 1 1 d . . . . .
H20A H 1.051(3) 0.390(3) 0.252(2) 0.056(7) Uiso 1 1 d . . . . .
H20B H 0.966(4) 0.216(3) 0.211(2) 0.066(8) Uiso 1 1 d . . . . .
H20C H 0.893(3) 0.314(3) 0.279(2) 0.061(8) Uiso 1 1 d . . . . .
C21 C 0.6461(2) 1.0132(2) 0.30912(14) 0.0461(5) Uani 1 1 d . . . . .
H21A H 0.550429 1.041840 0.306451 0.055 Uiso 0.61(3) 1 calc R U P A 1
H21B H 0.683969 1.020567 0.251017 0.055 Uiso 0.61(3) 1 calc R U P A 1
H21C H 0.550742 1.042315 0.307587 0.055 Uiso 0.39(3) 1 calc R U P A 2
H21D H 0.682075 1.020114 0.250396 0.055 Uiso 0.39(3) 1 calc R U P A 2
C22 C 0.7699(7) 1.1238(6) 0.3982(4) 0.0492(18) Uani 0.61(3) 1 d G U P A 1
C23 C 0.8971(11) 1.0866(7) 0.4337(7) 0.0586(19) Uani 0.61(3) 1 d G U P A 1
H23 H 0.906783 0.991919 0.403679 0.070 Uiso 0.61(3) 1 calc R U P A 1
C24 C 1.0101(10) 1.1880(9) 0.5131(8) 0.073(2) Uani 0.61(3) 1 d G U P A 1
H24 H 1.096973 1.162599 0.537300 0.088 Uiso 0.61(3) 1 calc R U P A 1
C25 C 0.9959(6) 1.3266(6) 0.5569(4) 0.061(2) Uani 0.61(3) 1 d G U P A 1
H25 H 1.073090 1.395915 0.611191 0.073 Uiso 0.61(3) 1 calc R U P A 1
C26 C 0.8687(10) 1.3638(8) 0.5215(5) 0.0554(16) Uani 0.61(3) 1 d G U P A 1
H26 H 0.859014 1.458554 0.551464 0.066 Uiso 0.61(3) 1 calc R U P A 1
C27 C 0.7557(9) 1.2624(9) 0.4421(5) 0.0443(14) Uani 0.61(3) 1 d G U P A 1
H27 H 0.668822 1.287876 0.417843 0.053 Uiso 0.61(3) 1 calc R U P A 1
C28 C 0.7671(11) 1.1197(10) 0.3938(6) 0.046(2) Uani 0.39(3) 1 d G U P A 2
C33 C 0.7313(12) 1.2336(16) 0.4556(9) 0.053(2) Uani 0.39(3) 1 d G U P A 2
H33 H 0.629643 1.240972 0.444062 0.064 Uiso 0.39(3) 1 calc R U P A 2
C32 C 0.8442(15) 1.3369(15) 0.5344(9) 0.065(3) Uani 0.39(3) 1 d G . P A 2
H32 H 0.819670 1.414750 0.576660 0.079 Uiso 0.39(3) 1 calc R U P A 2
C31 C 0.9929(12) 1.3262(11) 0.5513(7) 0.110(8) Uani 0.39(3) 1 d G . P A 2
H31 H 1.070005 1.396704 0.605145 0.132 Uiso 0.39(3) 1 calc R U P A 2
C30 C 1.0287(11) 1.2122(15) 0.4895(11) 0.070(3) Uani 0.39(3) 1 d G . P A 2
H30 H 1.130313 1.204881 0.501031 0.084 Uiso 0.39(3) 1 calc R U P A 2
C29 C 0.9158(13) 1.1090(13) 0.4107(10) 0.052(3) Uani 0.39(3) 1 d G . P A 2
H29 H 0.940288 1.031101 0.368432 0.063 Uiso 0.39(3) 1 calc R U P A 2
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0847
0 0 1 0.0624
0 -1 1 0.1059
0 1 -1 0.1314
1 0 0 0.0083
-1 0 0 0.0129
0 -1 0 0.1202
-1 2 0 0.1449
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
C16 O3 C17 121.76(14) . . ?
C21 N1 C1 111.96(17) . . ?
C21 N1 C11 111.53(14) . . ?
C1 N1 C11 113.28(16) . . ?
C9 N2 C10 108.57(16) . . ?
C9 N2 H2 125.5(17) . . ?
C10 N2 H2 125.1(16) . . ?
N1 C1 C2 110.80(18) . . ?
N1 C1 H1A 112.7(14) . . ?
C2 C1 H1A 108.8(13) . . ?
N1 C1 H1B 107.6(16) . . ?
C2 C1 H1B 111.2(15) . . ?
H1A C1 H1B 106(2) . . ?
C3 C2 C1 108.97(17) . . ?
C3 C2 H2A 111.8(16) . . ?
C1 C2 H2A 111.1(16) . . ?
C3 C2 H2B 107(2) . . ?
C1 C2 H2B 110.1(19) . . ?
H2A C2 H2B 108(2) . . ?
C10 C3 C4 107.39(17) . . ?
C10 C3 C2 120.8(2) . . ?
C4 C3 C2 131.78(19) . . ?
C5 C4 C9 119.0(2) . . ?
C5 C4 C3 134.6(2) . . ?
C9 C4 C3 106.40(17) . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 121.2(15) . . ?
C4 C5 H5 119.8(16) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.6(18) . . ?
C7 C6 H6 119.3(18) . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.9(17) . . ?
C6 C7 H7 118.4(17) . . ?
C7 C8 C9 117.3(2) . . ?
C7 C8 H8 123.6(13) . . ?
C9 C8 H8 119.1(13) . . ?
N2 C9 C8 129.95(18) . . ?
N2 C9 C4 108.11(17) . . ?
C8 C9 C4 121.94(19) . . ?
C3 C10 N2 109.53(18) . . ?
C3 C10 C11 126.48(17) . . ?
N2 C10 C11 123.97(16) . . ?
N1 C11 C10 108.35(14) . . ?
N1 C11 C12 114.60(15) . . ?
C10 C11 C12 110.85(16) . . ?
N1 C11 C13 105.05(15) . . ?
C10 C11 C13 107.36(14) . . ?
C12 C11 C13 110.25(16) . . ?
C11 C12 H12A 108.9(14) . . ?
C11 C12 H12B 108.8(16) . . ?
H12A C12 H12B 105(2) . . ?
C11 C12 H12C 111.5(15) . . ?
H12A C12 H12C 108.6(19) . . ?
H12B C12 H12C 114(2) . . ?
O1 C13 C14 121.89(19) . . ?
O1 C13 C11 121.90(17) . . ?
C14 C13 C11 116.20(16) . . ?
C16 C14 C13 110.38(14) . . ?
C16 C14 C15 107.58(17) . . ?
C13 C14 C15 109.9(2) . . ?
C16 C14 H14 109.7(13) . . ?
C13 C14 H14 107.6(14) . . ?
C15 C14 H14 111.7(14) . . ?
C14 C15 H15A 105.2(19) . . ?
C14 C15 H15B 107.5(18) . . ?
H15A C15 H15B 109(2) . . ?
C14 C15 H15C 109(2) . . ?
H15A C15 H15C 113(3) . . ?
H15B C15 H15C 113(3) . . ?
O2 C16 O3 126.06(17) . . ?
O2 C16 C14 124.32(17) . . ?
O3 C16 C14 109.56(15) . . ?
O3 C17 C18 109.46(16) . . ?
O3 C17 C20 101.77(15) . . ?
C18 C17 C20 111.9(2) . . ?
O3 C17 C19 109.23(17) . . ?
C18 C17 C19 113.81(18) . . ?
C20 C17 C19 109.96(18) . . ?
C17 C18 H18A 110.2(16) . . ?
C17 C18 H18B 113.2(15) . . ?
H18A C18 H18B 111(2) . . ?
C17 C18 H18C 111.9(17) . . ?
H18A C18 H18C 105(2) . . ?
H18B C18 H18C 105(2) . . ?
C17 C19 H19A 112.0(16) . . ?
C17 C19 H19B 113(2) . . ?
H19A C19 H19B 109(2) . . ?
C17 C19 H19C 105.2(19) . . ?
H19A C19 H19C 105(2) . . ?
H19B C19 H19C 113(3) . . ?
C17 C20 H20A 109.9(16) . . ?
C17 C20 H20B 108.6(17) . . ?
H20A C20 H20B 105(2) . . ?
C17 C20 H20C 111.8(18) . . ?
H20A C20 H20C 113(2) . . ?
H20B C20 H20C 108(2) . . ?
N1 C21 C28 113.3(4) . . ?
N1 C21 C22 113.1(3) . . ?
N1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N1 C21 H21C 108.9 . . ?
C28 C21 H21C 108.9 . . ?
N1 C21 H21D 108.9 . . ?
C28 C21 H21D 108.9 . . ?
H21C C21 H21D 107.7 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 120.2(4) . . ?
C27 C22 C21 119.8(4) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C33 C28 C29 120.0 . . ?
C33 C28 C21 119.1(7) . . ?
C29 C28 C21 120.9(7) . . ?
C32 C33 C28 120.0 . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.207(3) . ?
O2 C16 1.204(2) . ?
O3 C16 1.332(2) . ?
O3 C17 1.495(2) . ?
N1 C21 1.470(3) . ?
N1 C1 1.478(3) . ?
N1 C11 1.487(2) . ?
N2 C9 1.377(3) . ?
N2 C10 1.387(2) . ?
N2 H2 0.82(3) . ?
C1 C2 1.520(4) . ?
C1 H1A 1.02(2) . ?
C1 H1B 1.04(3) . ?
C2 C3 1.492(3) . ?
C2 H2A 0.99(3) . ?
C2 H2B 0.96(4) . ?
C3 C10 1.366(3) . ?
C3 C4 1.436(3) . ?
C4 C5 1.405(3) . ?
C4 C9 1.414(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.94(3) . ?
C6 C7 1.396(4) . ?
C6 H6 1.00(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.96(3) . ?
C8 C9 1.397(3) . ?
C8 H8 1.03(2) . ?
C10 C11 1.495(3) . ?
C11 C12 1.534(2) . ?
C11 C13 1.547(3) . ?
C12 H12A 1.01(3) . ?
C12 H12B 0.98(3) . ?
C12 H12C 1.06(3) . ?
C13 C14 1.527(2) . ?
C14 C16 1.521(3) . ?
C14 C15 1.529(3) . ?
C14 H14 0.97(2) . ?
C15 H15A 1.01(3) . ?
C15 H15B 1.00(3) . ?
C15 H15C 1.09(4) . ?
C17 C18 1.509(3) . ?
C17 C20 1.519(3) . ?
C17 C19 1.526(3) . ?
C18 H18A 0.97(3) . ?
C18 H18B 1.01(3) . ?
C18 H18C 0.97(3) . ?
C19 H19A 1.00(3) . ?
C19 H19B 1.02(4) . ?
C19 H19C 0.99(3) . ?
C20 H20A 1.00(3) . ?
C20 H20B 1.00(3) . ?
C20 H20C 0.93(3) . ?
C21 C28 1.480(8) . ?
C21 C22 1.539(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 C27 1.3900 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.3900 . ?
C28 C29 1.3900 . ?
C33 C32 1.3900 . ?
C33 H33 0.9500 . ?
C32 C31 1.3900 . ?
C32 H32 0.9500 . ?
C31 C30 1.3900 . ?
C31 H31 0.9500 . ?
C30 C29 1.3900 . ?
C30 H30 0.9500 . ?
C29 H29 0.9500 . ?
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
C21 N1 C1 C2 -166.36(16) . . . . ?
C11 N1 C1 C2 66.5(2) . . . . ?
N1 C1 C2 C3 -51.2(2) . . . . ?
C1 C2 C3 C10 20.2(3) . . . . ?
C1 C2 C3 C4 -158.6(2) . . . . ?
C10 C3 C4 C5 -177.7(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C10 C3 C4 C9 0.0(2) . . . . ?
C2 C3 C4 C9 178.9(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 178.0(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C10 N2 C9 C8 179.16(19) . . . . ?
C10 N2 C9 C4 -0.2(2) . . . . ?
C7 C8 C9 N2 -178.45(19) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C5 C4 C9 N2 178.26(18) . . . . ?
C3 C4 C9 N2 0.1(2) . . . . ?
C5 C4 C9 C8 -1.2(3) . . . . ?
C3 C4 C9 C8 -179.28(17) . . . . ?
C4 C3 C10 N2 -0.1(2) . . . . ?
C2 C3 C10 N2 -179.14(18) . . . . ?
C4 C3 C10 C11 178.41(17) . . . . ?
C2 C3 C10 C11 -0.6(3) . . . . ?
C9 N2 C10 C3 0.2(2) . . . . ?
C9 N2 C10 C11 -178.38(16) . . . . ?
C21 N1 C11 C10 -170.30(16) . . . . ?
C1 N1 C11 C10 -42.9(2) . . . . ?
C21 N1 C11 C12 -46.0(2) . . . . ?
C1 N1 C11 C12 81.4(2) . . . . ?
C21 N1 C11 C13 75.20(18) . . . . ?
C1 N1 C11 C13 -157.40(16) . . . . ?
C3 C10 C11 N1 11.0(3) . . . . ?
N2 C10 C11 N1 -170.66(16) . . . . ?
C3 C10 C11 C12 -115.5(2) . . . . ?
N2 C10 C11 C12 62.8(2) . . . . ?
C3 C10 C11 C13 124.0(2) . . . . ?
N2 C10 C11 C13 -57.7(2) . . . . ?
N1 C11 C13 O1 -121.7(2) . . . . ?
C10 C11 C13 O1 123.1(2) . . . . ?
C12 C11 C13 O1 2.3(3) . . . . ?
N1 C11 C13 C14 58.60(19) . . . . ?
C10 C11 C13 C14 -56.59(19) . . . . ?
C12 C11 C13 C14 -177.44(15) . . . . ?
O1 C13 C14 C16 -74.6(2) . . . . ?
C11 C13 C14 C16 105.10(18) . . . . ?
O1 C13 C14 C15 43.9(3) . . . . ?
C11 C13 C14 C15 -136.42(19) . . . . ?
C17 O3 C16 O2 2.6(3) . . . . ?
C17 O3 C16 C14 -174.53(16) . . . . ?
C13 C14 C16 O2 31.9(3) . . . . ?
C15 C14 C16 O2 -88.0(3) . . . . ?
C13 C14 C16 O3 -150.99(17) . . . . ?
C15 C14 C16 O3 89.1(2) . . . . ?
C16 O3 C17 C18 -65.4(2) . . . . ?
C16 O3 C17 C20 176.07(19) . . . . ?
C16 O3 C17 C19 59.8(2) . . . . ?
C1 N1 C21 C28 68.6(5) . . . . ?
C11 N1 C21 C28 -163.3(5) . . . . ?
C1 N1 C21 C22 67.6(4) . . . . ?
C11 N1 C21 C22 -164.3(3) . . . . ?
N1 C21 C22 C23 40.5(6) . . . . ?
N1 C21 C22 C27 -140.7(6) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 C24 178.8(5) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C21 C22 C27 C26 -178.8(5) . . . . ?
N1 C21 C28 C33 -119.7(9) . . . . ?
N1 C21 C28 C29 61.8(10) . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
C21 C28 C33 C32 -178.6(7) . . . . ?
C28 C33 C32 C31 0.0 . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C31 C30 C29 C28 0.0 . . . . ?
C33 C28 C29 C30 0.0 . . . . ?
C21 C28 C29 C30 178.5(8) . . . . ?
