DMT analogues: <i>N</i>-ethyl-<i>N</i>-propyltryptamine and <i>N</i>-allyl-<i>N</i>-methytryptamine as their hydrofumarate salts
Chadeayne, Andrew R.; Pham, Duyen N. K.; Golen, James A.; Manke, David R.; Acta Crystallographica Section E 76 (2020) 1201–1205; doi:10.1107/S2056989020008683

data_2243466
_publ_section_title
;
 DMT analogues: <i>N</i>-ethyl-<i>N</i>-propyltryptamine and
 <i>N</i>-allyl-<i>N</i>-methytryptamine as their hydrofumarate salts
;
_journal_coeditor_code           DX2028
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1201
_journal_page_last               1205
_journal_paper_doi               10.1107/S2056989020008683
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H23 N2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C15 H23 N2 +, C4 H3 O4 -'
_chemical_formula_sum            'C19 H26 N2 O4'
_chemical_formula_weight         346.42
_chemical_name_common
;
<i>N</i>-Ethyl-<i>N</i>-propyltryptammonium hydrofumarate
;
_chemical_name_systematic
;
[2-(1<i>H</i>-Indol-3-yl)ethyl](methyl)propylazanium
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 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.537(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4839(8)
_cell_length_b                   14.1752(14)
_cell_length_c                   9.6461(10)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.67
_cell_volume                     958.28(17)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.728
_diffrn_reflns_theta_min         2.874
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.135
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1509 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.10(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0553P)^2^+0.1111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                3368
_reflns_number_total             3570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2028sup1.cif
_cod_data_source_block           I
_cod_database_code               2243466
_cod_database_fobs_code          2243466
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.992
_shelx_hkl_checksum              67208
_shelx_res_checksum              54504