Bis(4-acetoxy-<i>N</i>,<i>N</i>-dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
Chadeayne, Andrew R.; Golen, James A.; Manke, David R.; Acta Crystallographica Section E 75 (2019) 900–902; doi:10.1107/S2056989019007370

data_2242962
_publ_section_title
;
 Bis(4-acetoxy-<i>N</i>,<i>N</i>-dimethyltryptammonium) fumarate: a new
 crystalline form of psilacetin, an alternative to psilocybin as a
 psilocin prodrug
;
_journal_coeditor_code           FF2159
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              900
_journal_page_last               902
_journal_paper_doi               10.1107/S2056989019007370
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '2C14 H19 N2 O2 +, C4 H2 O4 2-'
_chemical_formula_moiety         '2C14 H19 N2 O2 +, (C4 H2 O4 2-)'
_chemical_formula_sum            'C32 H40 N4 O8'
_chemical_formula_weight         608.68
_chemical_name_common
;
Bis(4-acetoxy-<i>N</i>,<i>N</i>-dimethyltryptammonium) fumarate
;
_chemical_name_systematic
;
Bis{2-[4-(acetyloxy)-1<i>H</i>-indol-3-yl]ethan-1-aminium} but-2-enedioate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.730(5)
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_cell_formula_units_Z            1
_cell_length_a                   8.3965(13)
_cell_length_b                   8.9879(14)
_cell_length_c                   12.0126(16)
_cell_measurement_reflns_used    6407
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.09
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_cell_volume                     784.2(2)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
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<i>APEX3</i> (Bruker, 2016)
;
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SAINT (Bruker, 2016)
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<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
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<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
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SHELXL97 (Sheldrick, 2008)
;
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SHELXT2014 (Sheldrick, 2015)
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_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21581
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.411
_diffrn_reflns_theta_min         3.343
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7135
_exptl_absorpt_correction_type   multi-scan
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;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0387P)^2^+0.3852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2087
_reflns_number_total             2877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ff2159sup1.cif
_cod_data_source_block           I
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_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              20167
_shelx_res_checksum              2422
_shelxl_version_number           2014/6
_cod_database_fobs_code 2242962