Structural characterization and comparative analysis of polymorphic forms of psilocin (4-hydroxy-N,N-dimethyltryptamine)
Zeller, Matthias; Parent, Stephan; Schultheiss, Nate; Acta Crystallographica Section E Crystallographic Communications 80 (2024) –; doi:10.1107/S2056989024004201

data_2023124
_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-<i>N</i>,<i>N</i>-dimethyltryptamine
;
_chemical_name_systematic
;
3-[2-(Dimethylamino)ethyl]-1<i>H</i>-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
;
<i>SHELXL2019/2</i> (Sheldrick, 2015b),
<i>ShelXle</i> Rev1580 (H\"ubschle <i>et al.</i>,  2011)
;
_computing_structure_solution
;
<i>SHELXT</i> (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       '\w 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/[\s^2^(Fo^2^)+(0.1062P)^2^+0.3139P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.976
_shelx_hkl_checksum              33189
_shelx_res_checksum              99522