#------------------------------------------------------------------------------
#$Date: 2024-05-15 04:58:38 +0300 (Wed, 15 May 2024) $
#$Revision: 291856 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023125.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_2023125
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_moiety         'C12 H16 N2 O'
_chemical_formula_sum            'C12 H16 N2 O'
_chemical_formula_weight         204.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 92.5663(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4041(4)
_cell_length_b                   8.5286(3)
_cell_length_c                   12.4087(4)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.0609
_cell_measurement_theta_min      3.0899
_cell_volume                     1099.95(7)
_computing_cell_refinement
;
SAINT V8.40B (Bruker, 2020)
;
_computing_data_collection
;
Apex4 v2022.10-0 (Bruker, 2022)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2020)
;
_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      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33575
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.195
_diffrn_reflns_theta_min         2.899
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS 2016/2; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         4199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0458
_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)+(0.0713P)²+0.1621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                3116
_reflns_number_total             4199
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8096.cif
_cod_data_source_block           Form_I_150K
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023125
_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   0.966
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.70597(7) 0.47588(8) 0.47509(5) 0.03151(16) Uani d 1 . .
H H1O 0.7335(17) 0.592(2) 0.4841(14) 0.071(5) Uiso d 1 . .
N N1 0.64472(10) 0.13425(11) 0.18670(7) 0.0385(2) Uani d 1 . .
H H1N 0.6505(15) 0.0898(19) 0.1202(13) 0.056(4) Uiso d 1 . .
N N2 0.24988(8) 0.22499(9) 0.49394(6) 0.02849(16) Uani d 1 . .
C C1 0.47558(9) 0.23991(11) 0.43345(7) 0.02952(18) Uani d 1 . .
H H1A 0.472877 0.351903 0.454214 0.035 Uiso calc 1 . .
H H1B 0.513277 0.180568 0.495733 0.035 Uiso calc 1 . .
C C5 0.54133(11) 0.12554(12) 0.25174(8) 0.0350(2) Uani d 1 . .
H H5 0.467292 0.062248 0.237856 0.042 Uiso calc 1 . .
C C6 0.56084(9) 0.22194(10) 0.33987(7) 0.02783(18) Uani d 1 . .
C C7 0.68352(9) 0.29695(10) 0.32686(7) 0.02674(18) Uani d 1 . .
C C8 0.75460(9) 0.41272(10) 0.38446(7) 0.02762(18) Uani d 1 . .
C C9 0.87124(10) 0.46122(13) 0.34568(9) 0.0357(2) Uani d 1 . .
H H9 0.920818 0.537842 0.384468 0.043 Uiso calc 1 . .
C C10 0.91725(11) 0.39842(14) 0.24952(9) 0.0415(3) Uani d 1 . .
H H10 0.997389 0.433933 0.224968 0.050 Uiso calc 1 . .
C C11 0.84970(11) 0.28788(14) 0.19068(9) 0.0403(3) Uani d 1 . .
H H11 0.881122 0.246287 0.125900 0.048 Uiso calc 1 . .
C C12 0.73231(10) 0.23859(11) 0.22993(7) 0.0324(2) Uani d 1 . .
C C2 0.33887(9) 0.18255(12) 0.40912(8) 0.0326(2) Uani d 1 . .
H H2A 0.306539 0.227858 0.339629 0.039 Uiso calc 1 . .
H H2B 0.339916 0.067070 0.401086 0.039 Uiso calc 1 . .
C C3 0.11742(11) 0.18671(17) 0.45855(11) 0.0477(3) Uani d 1 . .
H H3A 0.095506 0.240663 0.390463 0.072 Uiso calc 1 . .
H H3B 0.058665 0.220643 0.513544 0.072 Uiso calc 1 . .
H H3C 0.109444 0.073191 0.447973 0.072 Uiso calc 1 . .
C C4 0.28086(12) 0.14338(14) 0.59591(9) 0.0417(2) Uani d 1 . .
H H4A 0.274408 0.029888 0.584536 0.063 Uiso calc 1 . .
H H4B 0.220221 0.175593 0.649912 0.063 Uiso calc 1 . .
H H4C 0.368648 0.170138 0.621391 0.063 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C8 O1 H1O . . 110.8(10) ?
C12 N1 C5 . . 109.28(8) ?
C12 N1 H1N . . 123.8(10) ?
C5 N1 H1N . . 126.4(10) ?
C3 N2 C4 . . 108.68(9) ?
C3 N2 C2 . . 110.07(8) ?
C4 N2 C2 . . 112.18(8) ?
C6 C1 C2 . . 113.17(8) ?
C6 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
C6 C1 H1B . . 108.9 ?
C2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.8 ?
N1 C5 C6 . . 110.04(10) ?
N1 C5 H5 . . 125.0 ?
C6 C5 H5 . . 125.0 ?
C5 C6 C7 . . 106.01(8) ?
C5 C6 C1 . . 127.22(9) ?
C7 C6 C1 . . 126.71(8) ?
C8 C7 C12 . . 118.49(8) ?
C8 C7 C6 . . 134.47(8) ?
C12 C7 C6 . . 106.95(8) ?
O1 C8 C9 . . 122.01(9) ?
O1 C8 C7 . . 119.29(8) ?
C9 C8 C7 . . 118.69(8) ?
C8 C9 C10 . . 120.99(11) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C11 C10 C9 . . 121.84(10) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C10 C11 C12 . . 117.19(9) ?
C10 C11 H11 . . 121.4 ?
C12 C11 H11 . . 121.4 ?
N1 C12 C11 . . 129.50(9) ?
N1 C12 C7 . . 107.71(9) ?
C11 C12 C7 . . 122.78(10) ?
N2 C2 C1 . . 112.95(8) ?
N2 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
N2 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
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 ?
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
O1 C8 . 1.3645(10) ?
O1 H1O . 1.038(19) ?
N1 C12 . 1.3662(15) ?
N1 C5 . 1.3755(14) ?
N1 H1N . 0.913(16) ?
N2 C3 . 1.4644(14) ?
N2 C4 . 1.4672(13) ?
N2 C2 . 1.4776(12) ?
C1 C6 . 1.5004(12) ?
C1 C2 . 1.5215(14) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C5 C6 . 1.3759(13) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4432(13) ?
C7 C8 . 1.4090(13) ?
C7 C12 . 1.4165(12) ?
C8 C9 . 1.3884(13) ?
C9 C10 . 1.4110(15) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3674(18) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3995(15) ?
C11 H11 . 0.9500 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
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
O1 H1O N2 3_666 1.038(19) 1.590(19) 2.6175(10) 169.5(16) yes
N1 H1N O1 4_565 0.913(16) 1.995(17) 2.8867(11) 165.0(15) 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
C12 N1 C5 C6 . . . . -1.19(12) ?
N1 C5 C6 C7 . . . . 1.10(11) ?
N1 C5 C6 C1 . . . . -176.13(9) ?
C2 C1 C6 C5 . . . . -19.25(14) ?
C2 C1 C6 C7 . . . . 164.07(9) ?
C5 C6 C7 C8 . . . . 175.89(10) ?
C1 C6 C7 C8 . . . . -6.86(16) ?
C5 C6 C7 C12 . . . . -0.61(10) ?
C1 C6 C7 C12 . . . . 176.64(8) ?
C12 C7 C8 O1 . . . . 176.77(8) ?
C6 C7 C8 O1 . . . . 0.57(15) ?
C12 C7 C8 C9 . . . . -1.96(13) ?
C6 C7 C8 C9 . . . . -178.15(10) ?
O1 C8 C9 C10 . . . . -177.57(9) ?
C7 C8 C9 C10 . . . . 1.12(15) ?
C8 C9 C10 C11 . . . . -0.03(17) ?
C9 C10 C11 C12 . . . . -0.17(17) ?
C5 N1 C12 C11 . . . . -178.23(10) ?
C5 N1 C12 C7 . . . . 0.76(11) ?
C10 C11 C12 N1 . . . . 178.11(10) ?
C10 C11 C12 C7 . . . . -0.75(16) ?
C8 C7 C12 N1 . . . . -177.24(8) ?
C6 C7 C12 N1 . . . . -0.08(10) ?
C8 C7 C12 C11 . . . . 1.83(14) ?
C6 C7 C12 C11 . . . . 178.99(9) ?
C3 N2 C2 C1 . . . . 171.85(9) ?
C4 N2 C2 C1 . . . . -67.00(11) ?
C6 C1 C2 N2 . . . . -170.10(8) ?
