Psilacetin derivatives: fumarate salts of the methyl–ethyl, methyl–allyl and diallyl variants of the psilocin prodrug
Pham, Duyen N. K.; Chadeayne, Andrew R.; Golen, James A.; Manke, David R.; Acta Crystallographica Section E 77 (2021) 101–106; doi:10.1107/S2056989021000116

data_2243722
_publ_section_title
;
 Psilacetin derivatives: fumarate salts of the methyl--ethyl,
 methyl--allyl and diallyl variants of the psilocin prodrug
;
_journal_coeditor_code           HB7959
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              101
_journal_page_last               106
_journal_paper_doi               10.1107/S2056989021000116
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C16 H21 N2 O2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C16 H21 N2 O2 +, C4 H3 O4 -'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41
_chemical_name_systematic
;
[2-(4-Acetyloxy-1<i>H</i>-indol-3-yl)ethyl](methyl)prop-2-enylazanium
3-carboxyprop-2-enoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.394(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9702(4)
_cell_length_b                   14.1788(7)
_cell_length_c                   9.8035(5)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.68
_cell_volume                     1016.80(9)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26393
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.709
_diffrn_reflns_theta_min         2.785
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.164
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1577 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0592P)^2^+0.2448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                3516
_reflns_number_total             3797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7959sup1.cif
_cod_data_source_block           II
_cod_database_code               2243722
_cod_database_fobs_code          2243722
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              12472
_shelx_res_checksum              74221