#------------------------------------------------------------------------------
#$Date: 2024-05-15 04:58:38 +0300 (Wed, 15 May 2024) $
#$Revision: 291856 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023124.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023124
loop_
_publ_author_name
'Zeller, Matthias'
'Parent, Stephan'
'Schultheiss, Nate'
_publ_section_title
;
 Structural characterization and comparative analysis of polymorphic forms
 of psilocin (4-hydroxy-N,N-dimethyltryptamine)
;
_journal_coeditor_code           HB8096
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024004201
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H16 N2 O'
_chemical_formula_moiety         'C12 H16 N2 O'
_chemical_formula_sum            'C12 H16 N2 O'
_chemical_formula_weight         204.27
_chemical_name_common
;
4-Hydroxy-N,N-dimethyltryptamine
;
_chemical_name_systematic
;
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 107.490(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5331(7)
_cell_length_b                   8.9358(3)
_cell_length_c                   14.0279(7)
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0740
_cell_measurement_theta_min      4.9300
_cell_volume                     1139.73(12)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)
;
_computing_publication_material  'publCIF (Westrip, 2013)'
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b),
ShelXle Rev1580 (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset, Pilatus 200/300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.006
_diffrn_reflns_theta_min         4.992
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     532
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0645
_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)+(0.1062P)²+0.3139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2207
_reflns_number_gt                1754
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8096.cif
_cod_data_source_block           Form_II_293K
_cod_original_cell_volume        1139.73(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2023124
_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   0.806
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H H1 0.629(5) 0.548(5) 0.379(3) 0.120(13) Uiso d 1 . .
C C1 0.6049(6) 0.4321(5) 0.1961(3) 0.0786(12) Uani d 0.689(5) A 1
H H1A 0.701941 0.477062 0.218344 0.094 Uiso calc 0.689(5) A 1
H H1B 0.598839 0.374580 0.136326 0.094 Uiso calc 0.689(5) A 1
C C2 0.5891(7) 0.3248(5) 0.2772(3) 0.0793(11) Uani d 0.689(5) A 1
H H2A 0.485373 0.309139 0.268700 0.095 Uiso calc 0.689(5) A 1
H H2B 0.631533 0.228959 0.268722 0.095 Uiso calc 0.689(5) A 1
N N2 0.6602(6) 0.3790(7) 0.3790(4) 0.0700(13) Uani d 0.689(5) A 1
C C3 0.8215(7) 0.3657(8) 0.4111(6) 0.0991(18) Uani d 0.689(5) A 1
H H3A 0.848490 0.262228 0.410669 0.149 Uiso calc 0.689(5) A 1
H H3B 0.860680 0.405160 0.477477 0.149 Uiso calc 0.689(5) A 1
H H3C 0.860535 0.420937 0.366147 0.149 Uiso calc 0.689(5) A 1
C C4 0.6000(8) 0.3008(7) 0.4497(5) 0.0880(16) Uani d 0.689(5) A 1
H H4A 0.496721 0.321472 0.433727 0.132 Uiso calc 0.689(5) A 1
H H4B 0.649220 0.334574 0.516344 0.132 Uiso calc 0.689(5) A 1
H H4C 0.614668 0.195002 0.445389 0.132 Uiso calc 0.689(5) A 1
N N1 0.3190(10) 0.6949(9) 0.0677(6) 0.0731(15) Uani d 0.689(5) A 1
H H1N 0.253727 0.724472 0.014198 0.110 Uiso calc 0.689(5) A 1
C C5 0.3974(7) 0.5670(8) 0.0772(5) 0.0692(15) Uani d 0.689(5) A 1
H H5 0.387132 0.496668 0.026696 0.083 Uiso calc 0.689(5) A 1
C C6 0.4918(6) 0.5555(6) 0.1692(4) 0.0646(11) Uani d 0.689(5) A 1
C C7 0.4692(9) 0.6852(8) 0.2248(5) 0.0557(14) Uani d 0.689(5) A 1
C C8 0.5353(6) 0.7405(7) 0.3216(4) 0.0573(12) Uani d 0.689(5) A 1
C C9 0.4903(8) 0.8781(8) 0.3460(6) 0.0651(16) Uani d 0.689(5) A 1
H H9 0.533483 0.918116 0.409263 0.078 Uiso calc 0.689(5) A 1
C C10 0.3792(13) 0.9580(11) 0.2755(6) 0.0687(18) Uani d 0.689(5) A 1
H H10 0.346823 1.047946 0.294841 0.082 Uiso calc 0.689(5) A 1
C C11 0.3173(13) 0.9095(11) 0.1803(6) 0.0683(17) Uani d 0.689(5) A 1
H H11 0.249568 0.967390 0.133219 0.082 Uiso calc 0.689(5) A 1
C C12 0.3599(13) 0.7700(10) 0.1570(6) 0.0570(13) Uani d 0.689(5) A 1
O O1 0.6453(5) 0.6668(4) 0.3906(3) 0.0720(9) Uani d 0.689(5) A 1
C C1B 0.5012(11) 0.3867(10) 0.2090(7) 0.078(2) Uani d 0.311(5) A 2
H H1C 0.478936 0.323039 0.150278 0.094 Uiso calc 0.311(5) A 2
H H1D 0.446315 0.348423 0.251780 0.094 Uiso calc 0.311(5) A 2
C C2B 0.6645(12) 0.3715(13) 0.2644(7) 0.079(2) Uani d 0.311(5) A 2
H H2C 0.696312 0.270113 0.257242 0.095 Uiso calc 0.311(5) A 2
H H2D 0.720114 0.439026 0.235409 0.095 Uiso calc 0.311(5) A 2
N N2B 0.6939(15) 0.4062(19) 0.3706(9) 0.073(3) Uani d 0.311(5) A 2
C C3B 0.8539(14) 0.443(2) 0.4141(14) 0.105(4) Uani d 0.311(5) A 2
H H3D 0.911578 0.355453 0.411664 0.158 Uiso calc 0.311(5) A 2
H H3E 0.872839 0.473878 0.482286 0.158 Uiso calc 0.311(5) A 2
H H3F 0.879671 0.521794 0.376268 0.158 Uiso calc 0.311(5) A 2
C C4B 0.6546(16) 0.2889(18) 0.4287(12) 0.096(3) Uani d 0.311(5) A 2
H H4D 0.549796 0.276267 0.407503 0.143 Uiso calc 0.311(5) A 2
H H4E 0.687337 0.315529 0.498172 0.143 Uiso calc 0.311(5) A 2
H H4F 0.700690 0.197023 0.418951 0.143 Uiso calc 0.311(5) A 2
N N1B 0.306(2) 0.722(2) 0.0774(13) 0.068(2) Uani d 0.311(5) A 2
H H1NB 0.248617 0.762923 0.024437 0.102 Uiso calc 0.311(5) A 2
C C5B 0.3611(15) 0.5824(19) 0.0815(11) 0.065(2) Uani d 0.311(5) A 2
H H5B 0.343952 0.519523 0.026288 0.078 Uiso calc 0.311(5) A 2
C C6B 0.4454(12) 0.5433(12) 0.1756(10) 0.067(2) Uani d 0.311(5) A 2
C C7B 0.446(2) 0.6822(18) 0.2322(11) 0.055(2) Uani d 0.311(5) A 2
C C8B 0.4966(13) 0.7291(15) 0.3325(9) 0.056(2) Uani d 0.311(5) A 2
C C9B 0.4612(18) 0.8680(16) 0.3603(12) 0.058(2) Uani d 0.311(5) A 2
H H9B 0.499146 0.895479 0.427087 0.070 Uiso calc 0.311(5) A 2
C C10B 0.374(3) 0.968(2) 0.2955(13) 0.059(2) Uani d 0.311(5) A 2
H H10B 0.357485 1.063956 0.316512 0.071 Uiso calc 0.311(5) A 2
C C11B 0.312(3) 0.924(2) 0.2009(13) 0.059(2) Uani d 0.311(5) A 2
H H11B 0.241889 0.984553 0.156808 0.071 Uiso calc 0.311(5) A 2
C C12B 0.352(3) 0.788(2) 0.1687(14) 0.058(2) Uani d 0.311(5) A 2
O O1B 0.5739(11) 0.6420(9) 0.4069(5) 0.076(2) Uani d 0.311(5) 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 114.9(4) ?
C6 C1 H1A . . 108.5 ?
C2 C1 H1A . . 108.5 ?
C6 C1 H1B . . 108.5 ?
C2 C1 H1B . . 108.5 ?
H1A C1 H1B . . 107.5 ?
N2 C2 C1 . . 113.5(4) ?
N2 C2 H2A . . 108.9 ?
C1 C2 H2A . . 108.9 ?
N2 C2 H2B . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
C4 N2 C2 . . 110.0(5) ?
C4 N2 C3 . . 109.9(5) ?
C2 N2 C3 . . 113.9(6) ?
N2 C3 H3A . . 109.5 ?
N2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N2 C4 H4A . . 109.5 ?
N2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C5 N1 C12 . . 109.1(6) ?
C5 N1 H1N . . 125.4 ?
C12 N1 H1N . . 125.4 ?
C6 C5 N1 . . 110.7(5) ?
C6 C5 H5 . . 124.7 ?
N1 C5 H5 . . 124.7 ?
C5 C6 C7 . . 107.0(5) ?
C5 C6 C1 . . 121.4(5) ?
C7 C6 C1 . . 131.3(5) ?
C8 C7 C12 . . 119.4(5) ?
C8 C7 C6 . . 134.9(5) ?
C12 C7 C6 . . 105.5(4) ?
O1 C8 C9 . . 118.9(5) ?
O1 C8 C7 . . 122.9(5) ?
C9 C8 C7 . . 118.2(5) ?
C8 C9 C10 . . 120.1(6) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 122.8(7) ?
C11 C10 H10 . . 118.6 ?
C9 C10 H10 . . 118.6 ?
C10 C11 C12 . . 116.7(6) ?
C10 C11 H11 . . 121.6 ?
C12 C11 H11 . . 121.6 ?
N1 C12 C11 . . 129.5(6) ?
N1 C12 C7 . . 107.7(5) ?
C11 C12 C7 . . 122.6(6) ?
C8 O1 H1 . . 109(2) ?
C6B C1B C2B . . 116.7(8) ?
C6B C1B H1C . . 108.1 ?
C2B C1B H1C . . 108.1 ?
C6B C1B H1D . . 108.1 ?
C2B C1B H1D . . 108.1 ?
H1C C1B H1D . . 107.3 ?
N2B C2B C1B . . 110.8(9) ?
N2B C2B H2C . . 109.5 ?
C1B C2B H2C . . 109.5 ?
N2B C2B H2D . . 109.5 ?
C1B C2B H2D . . 109.5 ?
H2C C2B H2D . . 108.1 ?
C4B N2B C2B . . 114.7(13) ?
C4B N2B C3B . . 109.4(12) ?
C2B N2B C3B . . 108.7(12) ?
C4B N2B H1 . . 114(2) ?
C2B N2B H1 . . 108.3(19) ?
C3B N2B H1 . . 101(2) ?
N2B C3B H3D . . 109.5 ?
N2B C3B H3E . . 109.5 ?
H3D C3B H3E . . 109.5 ?
N2B C3B H3F . . 109.5 ?
H3D C3B H3F . . 109.5 ?
H3E C3B H3F . . 109.5 ?
N2B C4B H4D . . 109.5 ?
N2B C4B H4E . . 109.5 ?
H4D C4B H4E . . 109.5 ?
N2B C4B H4F . . 109.5 ?
H4D C4B H4F . . 109.5 ?
H4E C4B H4F . . 109.5 ?
C5B N1B C12B . . 110.4(12) ?
C5B N1B H1NB . . 124.8 ?
C12B N1B H1NB . . 124.8 ?
N1B C5B C6B . . 112.7(12) ?
N1B C5B H5B . . 123.6 ?
C6B C5B H5B . . 123.6 ?
C5B C6B C7B . . 102.2(10) ?
C5B C6B C1B . . 125.6(11) ?
C7B C6B C1B . . 131.7(10) ?
C8B C7B C12B . . 113.1(11) ?
C8B C7B C6B . . 137.3(12) ?
C12B C7B C6B . . 108.8(10) ?
O1B C8B C9B . . 115.5(10) ?
O1B C8B C7B . . 123.5(11) ?
C9B C8B C7B . . 120.9(10) ?
C10B C9B C8B . . 123.9(12) ?
C10B C9B H9B . . 118.1 ?
C8B C9B H9B . . 118.1 ?
C11B C10B C9B . . 117.7(14) ?
C11B C10B H10B . . 121.2 ?
C9B C10B H10B . . 121.2 ?
C10B C11B C12B . . 119.6(14) ?
C10B C11B H11B . . 120.2 ?
C12B C11B H11B . . 120.2 ?
N1B C12B C11B . . 129.8(13) ?
N1B C12B C7B . . 105.7(11) ?
C11B C12B C7B . . 124.4(13) ?
C8B O1B H1 . . 111(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.509(6) ?
C1 C2 . 1.530(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N2 . 1.466(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
N2 C4 . 1.463(7) ?
N2 C3 . 1.471(7) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
N1 C5 . 1.350(7) ?
N1 C12 . 1.370(6) ?
N1 H1N . 0.8600 ?
C5 C6 . 1.337(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.449(6) ?
C7 C8 . 1.403(6) ?
C7 C12 . 1.404(6) ?
C8 O1 . 1.364(5) ?
C8 C9 . 1.379(7) ?
C9 C10 . 1.408(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.358(7) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(7) ?
C11 H11 . 0.9300 ?
O1 H1 . 1.08(5) ?
C1B C6B . 1.521(12) ?
C1B C2B . 1.523(12) ?
C1B H1C . 0.9700 ?
C1B H1D . 0.9700 ?
C2B N2B . 1.463(13) ?
C2B H2C . 0.9700 ?
C2B H2D . 0.9700 ?
N2B C4B . 1.444(14) ?
N2B C3B . 1.498(14) ?
N2B H1 . 1.43(5) ?
C3B H3D . 0.9600 ?
C3B H3E . 0.9600 ?
C3B H3F . 0.9600 ?
C4B H4D . 0.9600 ?
C4B H4E . 0.9600 ?
C4B H4F . 0.9600 ?
N1B C5B . 1.347(13) ?
N1B C12B . 1.359(13) ?
N1B H1NB . 0.8600 ?
C5B C6B . 1.368(13) ?
C5B H5B . 0.9300 ?
C6B C7B . 1.472(12) ?
C7B C8B . 1.407(12) ?
C7B C12B . 1.416(13) ?
C8B O1B . 1.333(11) ?
C8B C9B . 1.374(12) ?
C9B C10B . 1.369(13) ?
C9B H9B . 0.9300 ?
C10B C11B . 1.340(13) ?
C10B H10B . 0.9300 ?
C11B C12B . 1.397(13) ?
C11B H11B . 0.9300 ?
O1B H1 . 1.12(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 4_575 0.86 1.99 2.823(8) 164 yes
N1B H1NB O1B 4_575 0.86 2.14 2.984(18) 169 yes
O1 H1 N2 1_555 1.08(5) 1.54(5) 2.584(8) 161(4) yes
O1B H1 N2B 1_555 1.12(5) 1.43(5) 2.52(2) 162(4) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 N2 . . . . -84.6(6) ?
C1 C2 N2 C4 . . . . 160.7(5) ?
C1 C2 N2 C3 . . . . -75.4(6) ?
C12 N1 C5 C6 . . . . -1.3(8) ?
N1 C5 C6 C7 . . . . 1.9(7) ?
N1 C5 C6 C1 . . . . -172.9(5) ?
C2 C1 C6 C5 . . . . -117.6(6) ?
C2 C1 C6 C7 . . . . 69.1(8) ?
C5 C6 C7 C8 . . . . -177.2(8) ?
C1 C6 C7 C8 . . . . -3.3(13) ?
C5 C6 C7 C12 . . . . -1.6(9) ?
C1 C6 C7 C12 . . . . 172.3(7) ?
C12 C7 C8 O1 . . . . -177.9(8) ?
C6 C7 C8 O1 . . . . -2.8(12) ?
C12 C7 C8 C9 . . . . -0.4(11) ?
C6 C7 C8 C9 . . . . 174.7(8) ?
O1 C8 C9 C10 . . . . 178.6(7) ?
C7 C8 C9 C10 . . . . 1.1(10) ?
C8 C9 C10 C11 . . . . -3.6(14) ?
C9 C10 C11 C12 . . . . 5.1(16) ?
C5 N1 C12 C11 . . . . 174.9(11) ?
C5 N1 C12 C7 . . . . 0.2(10) ?
C10 C11 C12 N1 . . . . -178.3(12) ?
C10 C11 C12 C7 . . . . -4.4(16) ?
C8 C7 C12 N1 . . . . 177.3(8) ?
C6 C7 C12 N1 . . . . 0.8(10) ?
C8 C7 C12 C11 . . . . 2.2(15) ?
C6 C7 C12 C11 . . . . -174.3(10) ?
C6B C1B C2B N2B . . . . 83.2(13) ?
C1B C2B N2B C4B . . . . 76.8(14) ?
C1B C2B N2B C3B . . . . -160.4(12) ?
C12B N1B C5B C6B . . . . 1.6(15) ?
N1B C5B C6B C7B . . . . -3.9(10) ?
N1B C5B C6B C1B . . . . 168.7(12) ?
C2B C1B C6B C5B . . . . 130.1(10) ?
C2B C1B C6B C7B . . . . -59.5(17) ?
C5B C6B C7B C8B . . . . 173(2) ?
C1B C6B C7B C8B . . . . 1(3) ?
C5B C6B C7B C12B . . . . 4.8(19) ?
C1B C6B C7B C12B . . . . -167.2(18) ?
C12B C7B C8B O1B . . . . 173.0(19) ?
C6B C7B C8B O1B . . . . 5(3) ?
C12B C7B C8B C9B . . . . -3(3) ?
C6B C7B C8B C9B . . . . -171.8(19) ?
O1B C8B C9B C10B . . . . -175.0(17) ?
C7B C8B C9B C10B . . . . 2(2) ?
C8B C9B C10B C11B . . . . 4(3) ?
C9B C10B C11B C12B . . . . -8(3) ?
C5B N1B C12B C11B . . . . -173(3) ?
C5B N1B C12B C7B . . . . 2(2) ?
C10B C11B C12B N1B . . . . -180(3) ?
C10B C11B C12B C7B . . . . 6(4) ?
C8B C7B C12B N1B . . . . -175.7(18) ?
C6B C7B C12B N1B . . . . -4(3) ?
C8B C7B C12B C11B . . . . 0(4) ?
C6B C7B C12B C11B . . . . 171(2) ?
