The fumarate salts of the <i>N</i>-isopropyl-<i>N</i>-methyl derivatives of DMT and psilocin
Chadeayne, Andrew R.; Pham, Duyen N. K.; Golen, James A.; Manke, David R.; Acta Crystallographica Section E 75 (2019) 1316–1320; doi:10.1107/S2056989019011253

data_2243055
_publ_section_title
;
 The fumarate salts of the <i>N</i>-isopropyl-<i>N</i>-methyl derivatives
 of DMT and psilocin
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1316
_journal_page_last               1320
_journal_paper_doi               10.1107/S2056989019011253
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H21 N2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C14 H21 N2 +, C4 H3 O4 -'
_chemical_formula_sum            'C18 H24 N2 O4'
_chemical_formula_weight         332.39
_chemical_name_common
;
<i>N</i>-Isopropyl-<i>N</i>-methyltryptaminium fumarate
;
_chemical_name_systematic
;
[2-(1<i>H</i>-Indol-3-yl)ethyl](methyl)propan-2-ylazanium
3-carboxyprop-2-enoate
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 106.932(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.852(2)
_cell_length_b                   12.789(2)
_cell_length_c                   14.875(3)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      3.04
_cell_volume                     1793.0(6)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.439
_diffrn_reflns_theta_min         3.044
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0488P)^2^+1.0971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                2605
_reflns_number_total             3297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7844sup1.cif
_cod_data_source_block           MiPT
_cod_database_code               2243055
_cod_database_fobs_code          2243055
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.996
_shelx_hkl_checksum              28248
_shelx_res_checksum              36350
_shelxl_version_number           2014/6