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_2243467
_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_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_absolute_configuration unk
_chemical_formula_iupac          'C14 H19 N2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C14 H19 N2 +, C4 H3 O4 -'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.37
_chemical_name_common
;
<i>N</i>-Allyl-<i>N</i>-methyltryptammonium (MALT) hydrofumarate
;
_chemical_name_systematic
;
[2-(1<i>H</i>-Indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium
3-carboxyprop-2-enoate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9845(7)
_cell_length_b                   8.5641(6)
_cell_length_c                   25.649(2)
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.60
_cell_measurement_theta_min      2.67
_cell_volume                     1753.9(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0463
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            49712
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.714
_diffrn_reflns_theta_min         2.672
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1177 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.035(7)
_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   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0615P)^2^+0.9658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                3036
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2028sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        1753.9(3)
_cod_database_code               2243467
_cod_database_fobs_code          2243467
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.987
_shelx_hkl_checksum              12180
_shelx_res_checksum              36461