#------------------------------------------------------------------------------
#$Date: 2020-07-04 08:15:10 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243466.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243466
loop_
_publ_author_name
'Chadeayne, Andrew R.'
'Pham, Duyen N. K.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 DMT analogues: N-ethyl-N-propyltryptamine and
 N-allyl-N-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
;
N-Ethyl-N-propyltryptammonium hydrofumarate
;
_chemical_name_systematic
;
[2-(1H-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
;
OLEX2 (Dolomanov et al.,  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       'φ and ω 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 x determined using 1509 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.10(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0553P)²+0.1111P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            dx2028sup1.cif
_cod_data_source_block           I
_cod_database_code               2243466
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3041(2) 0.35379(16) 0.3731(2) 0.0636(6) Uani d 1 . .
O O2 0.3509(2) 0.30983(15) 0.60295(19) 0.0550(5) Uani d 1 . .
O O3 0.9978(2) 0.31611(16) 0.55428(18) 0.0536(5) Uani d 1 . .
H H3A 1.120(5) 0.310(3) 0.574(3) 0.072(9) Uiso d 1 . .
O O4 1.0767(2) 0.31972(18) 0.79838(19) 0.0628(5) Uani d 1 . .
C C16 0.4059(3) 0.32758(15) 0.4973(2) 0.0374(5) Uani d 1 . .
C C17 0.6144(3) 0.31743(17) 0.5214(2) 0.0398(5) Uani d 1 . .
H H17 0.648978 0.306853 0.439068 0.048 Uiso calc 1 . .
C C18 0.7503(3) 0.32251(17) 0.6508(2) 0.0399(5) Uani d 1 . .
H H18 0.714909 0.328760 0.733678 0.048 Uiso calc 1 . .
C C19 0.9582(3) 0.31898(16) 0.6750(2) 0.0391(5) Uani d 1 . .
N N1 0.5831(3) 0.69330(14) 0.1173(2) 0.0475(5) Uani d 1 . .
H H1 0.651(4) 0.7437(15) 0.155(3) 0.065(9) Uiso d 1 . .
N N2 0.0093(3) 0.45996(14) 0.2087(2) 0.0419(5) Uani d 1 . .
H H2 0.094(3) 0.4206(14) 0.265(2) 0.037(6) Uiso d 1 . .
C C1 0.4632(4) 0.64176(18) 0.1676(3) 0.0482(5) Uani d 1 . .
H H1A 0.439846 0.654133 0.254380 0.058 Uiso calc 1 . .
C C2 0.5831(3) 0.65482(16) -0.0128(3) 0.0432(5) Uani d 1 . .
C C3 0.6784(4) 0.6830(2) -0.1055(3) 0.0564(6) Uani d 1 . .
H H3 0.758417 0.735307 -0.083577 0.068 Uiso calc 1 . .
C C4 0.6504(5) 0.6308(2) -0.2307(3) 0.0652(8) Uani d 1 . .
H H4 0.711949 0.648402 -0.295338 0.078 Uiso calc 1 . .
C C5 0.5309(4) 0.5516(2) -0.2637(3) 0.0608(7) Uani d 1 . .
H H5 0.516645 0.517150 -0.349024 0.073 Uiso calc 1 . .
C C6 0.4343(3) 0.52355(17) -0.1731(3) 0.0486(6) Uani d 1 . .
H H6 0.354963 0.470958 -0.196039 0.058 Uiso calc 1 . .
C C7 0.4587(3) 0.57658(16) -0.0449(2) 0.0402(5) Uani d 1 . .
C C8 0.3830(3) 0.56958(17) 0.0720(2) 0.0426(5) Uani d 1 . .
C C9 0.2459(4) 0.4953(2) 0.0840(3) 0.0550(6) Uani d 1 . .
H H9A 0.316656 0.442561 0.141476 0.066 Uiso calc 1 . .
H H9B 0.171567 0.472362 -0.014058 0.066 Uiso calc 1 . .
C C10 0.1139(4) 0.53459(19) 0.1570(3) 0.0558(6) Uani d 1 . .
H H10A 0.187623 0.572677 0.241152 0.067 Uiso calc 1 . .
H H10B 0.021466 0.575561 0.087367 0.067 Uiso calc 1 . .
C C11 -0.0973(4) 0.5018(2) 0.2997(3) 0.0533(6) Uani d 1 . .
H H11A -0.187131 0.548153 0.240391 0.064 Uiso calc 1 . .
H H11B -0.169895 0.452430 0.325308 0.064 Uiso calc 1 . .
C C12 0.0298(5) 0.5481(2) 0.4390(4) 0.0681(8) Uani d 1 . .
H H12A 0.131071 0.504882 0.492510 0.082 Uiso calc 1 . .
H H12B 0.087974 0.603660 0.414204 0.082 Uiso calc 1 . .
C C13 -0.0794(7) 0.5757(3) 0.5350(5) 0.0955(12) Uani d 1 . .
H H13A 0.005795 0.602901 0.625092 0.143 Uiso calc 1 . .
H H13B -0.139369 0.520900 0.557867 0.143 Uiso calc 1 . .
H H13C -0.175280 0.621019 0.484177 0.143 Uiso calc 1 . .
C C14 -0.108(2) 0.3898(9) 0.0926(13) 0.052(3) Uani d 0.5 A 1
H H14A -0.039029 0.375936 0.026374 0.062 Uiso calc 0.5 A 1
H H14B -0.227066 0.419643 0.034355 0.062 Uiso calc 0.5 A 1
C C15 -0.1542(12) 0.2941(8) 0.1545(13) 0.080(3) Uani d 0.5 A 1
H H15A -0.038462 0.266848 0.220982 0.120 Uiso calc 0.5 A 1
H H15B -0.212182 0.251470 0.073842 0.120 Uiso calc 0.5 A 1
H H15C -0.240528 0.305477 0.206447 0.120 Uiso calc 0.5 A 1
C C14A -0.126(2) 0.4138(10) 0.0749(14) 0.058(4) Uani d 0.5 A 2
H H14C -0.057294 0.389263 0.014130 0.070 Uiso calc 0.5 A 2
H H14D -0.218490 0.459560 0.016775 0.070 Uiso calc 0.5 A 2
C C15A -0.2296(15) 0.3328(8) 0.1217(12) 0.087(3) Uani d 0.5 A 2
H H15D -0.137282 0.289846 0.184512 0.131 Uiso calc 0.5 A 2
H H15E -0.309931 0.299929 0.035253 0.131 Uiso calc 0.5 A 2
H H15F -0.306261 0.358052 0.174491 0.131 Uiso calc 0.5 A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O3 H3A . . 111(2) ?
O1 C16 O2 . . 125.89(18) ?
O1 C16 C17 . . 115.76(18) ?
O2 C16 C17 . . 118.35(17) ?
C16 C17 H17 . . 117.9 ?
C18 C17 C16 . . 124.14(19) ?
C18 C17 H17 . . 117.9 ?
C17 C18 H18 . . 117.7 ?
C17 C18 C19 . . 124.55(19) ?
C19 C18 H18 . . 117.7 ?
O3 C19 C18 . . 114.52(18) ?
O4 C19 O3 . . 124.26(18) ?
O4 C19 C18 . . 121.21(19) ?
C1 N1 H1 . . 130(2) ?
C2 N1 H1 . . 121(2) ?
C2 N1 C1 . . 108.84(19) ?
C10 N2 H2 . . 107.8(16) ?
C10 N2 C14 . . 116.6(6) ?
C11 N2 H2 . . 108.1(16) ?
C11 N2 C10 . . 111.2(2) ?
C11 N2 C14 . . 113.7(7) ?
C14 N2 H2 . . 98.1(17) ?
C14A N2 H2 . . 112.4(17) ?
C14A N2 C10 . . 107.3(5) ?
C14A N2 C11 . . 110.0(7) ?
N1 C1 H1A . . 124.8 ?
C8 C1 N1 . . 110.3(2) ?
C8 C1 H1A . . 124.8 ?
N1 C2 C3 . . 130.1(2) ?
N1 C2 C7 . . 107.6(2) ?
C3 C2 C7 . . 122.3(2) ?
C2 C3 H3 . . 121.3 ?
C4 C3 C2 . . 117.4(3) ?
C4 C3 H3 . . 121.3 ?
C3 C4 H4 . . 119.3 ?
C3 C4 C5 . . 121.5(3) ?
C5 C4 H4 . . 119.3 ?
C4 C5 H5 . . 119.2 ?
C6 C5 C4 . . 121.5(3) ?
C6 C5 H5 . . 119.2 ?
C5 C6 H6 . . 121.0 ?
C5 C6 C7 . . 118.1(2) ?
C7 C6 H6 . . 121.0 ?
C2 C7 C8 . . 107.13(19) ?
C6 C7 C2 . . 119.1(2) ?
C6 C7 C8 . . 133.8(2) ?
C1 C8 C7 . . 106.1(2) ?
C1 C8 C9 . . 128.5(2) ?
C7 C8 C9 . . 125.4(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
C8 C9 C10 . . 110.8(2) ?
H9A C9 H9B . . 108.1 ?
C10 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
N2 C10 C9 . . 113.5(2) ?
N2 C10 H10A . . 108.9 ?
N2 C10 H10B . . 108.9 ?
C9 C10 H10A . . 108.9 ?
C9 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.7 ?
N2 C11 H11A . . 108.9 ?
N2 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C12 C11 N2 . . 113.4(2) ?
C12 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C11 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C13 C12 C11 . . 111.1(3) ?
C13 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13B . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 H14A . . 108.4 ?
N2 C14 H14B . . 108.4 ?
N2 C14 C15 . . 115.6(8) ?
H14A C14 H14B . . 107.5 ?
C15 C14 H14A . . 108.4 ?
C15 C14 H14B . . 108.4 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 C14A H14C . . 109.8 ?
N2 C14A H14D . . 109.8 ?
N2 C14A C15A . . 109.5(9) ?
H14C C14A H14D . . 108.2 ?
C15A C14A H14C . . 109.8 ?
C15A C14A H14D . . 109.8 ?
C14A C15A H15D . . 109.5 ?
C14A C15A H15E . . 109.5 ?
C14A C15A H15F . . 109.5 ?
H15D C15A H15E . . 109.5 ?
H15D C15A H15F . . 109.5 ?
H15E C15A H15F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 . 1.230(3) ?
O2 C16 . 1.251(3) ?
O3 H3A . 0.87(4) ?
O3 C19 . 1.299(3) ?
O4 C19 . 1.210(3) ?
C16 C17 . 1.502(3) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.307(3) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.491(3) ?
N1 H1 . 0.880(14) ?
N1 C1 . 1.371(3) ?
N1 C2 . 1.368(3) ?
N2 H2 . 0.873(13) ?
N2 C10 . 1.502(3) ?
N2 C11 . 1.500(3) ?
N2 C14 . 1.524(10) ?
N2 C14A . 1.485(10) ?
C1 H1A . 0.9300 ?
C1 C8 . 1.367(3) ?
C2 C3 . 1.384(3) ?
C2 C7 . 1.411(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.367(4) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.401(4) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.375(4) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.403(3) ?
C7 C8 . 1.432(3) ?
C8 C9 . 1.503(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.506(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C11 C12 . 1.498(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 C13 . 1.487(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.569(11) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C14A H14C . 0.9700 ?
C14A H14D . 0.9700 ?
C14A C15A . 1.539(11) ?
C15A H15D . 0.9600 ?
C15A H15E . 0.9600 ?
C15A H15F . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 1_655 0.87(4) 1.65(4) 2.518(2) 174(4) yes
N1 H1 O2 2_656 0.880(14) 2.52(3) 3.053(3) 119(2) yes
N1 H1 O4 2_756 0.880(14) 2.20(2) 2.984(3) 147(3) yes
N2 H2 O1 . 0.873(13) 1.820(14) 2.682(2) 169(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C16 C17 C18 . . . . 155.5(3) ?
O2 C16 C17 C18 . . . . -24.0(4) ?
C16 C17 C18 C19 . . . . -175.7(2) ?
C17 C18 C19 O3 . . . . 4.1(3) ?
C17 C18 C19 O4 . . . . -176.6(3) ?
N1 C1 C8 C7 . . . . 0.3(3) ?
N1 C1 C8 C9 . . . . 179.2(2) ?
N1 C2 C3 C4 . . . . -179.5(3) ?
N1 C2 C7 C6 . . . . -179.4(2) ?
N1 C2 C7 C8 . . . . 0.1(2) ?
N2 C11 C12 C13 . . . . -171.7(3) ?
C1 N1 C2 C3 . . . . 178.7(2) ?
C1 N1 C2 C7 . . . . 0.1(2) ?
C1 C8 C9 C10 . . . . 33.9(4) ?
C2 N1 C1 C8 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C2 C7 C8 C1 . . . . -0.2(2) ?
C2 C7 C8 C9 . . . . -179.2(2) ?
C3 C2 C7 C6 . . . . 1.8(3) ?
C3 C2 C7 C8 . . . . -178.7(2) ?
C3 C4 C5 C6 . . . . 1.0(5) ?
C4 C5 C6 C7 . . . . -0.2(4) ?
C5 C6 C7 C2 . . . . -1.2(3) ?
C5 C6 C7 C8 . . . . 179.5(2) ?
C6 C7 C8 C1 . . . . 179.2(2) ?
C6 C7 C8 C9 . . . . 0.2(4) ?
C7 C2 C3 C4 . . . . -1.0(4) ?
C7 C8 C9 C10 . . . . -147.4(2) ?
C8 C9 C10 N2 . . . . -164.8(2) ?
C10 N2 C11 C12 . . . . -62.5(3) ?
C10 N2 C14 C15 . . . . 159.0(9) ?
C10 N2 C14A C15A . . . . 176.9(9) ?
C11 N2 C10 C9 . . . . 171.7(2) ?
C11 N2 C14 C15 . . . . -69.5(13) ?
C11 N2 C14A C15A . . . . -61.9(12) ?
C14 N2 C10 C9 . . . . -55.8(8) ?
C14 N2 C11 C12 . . . . 163.5(6) ?
C14A N2 C10 C9 . . . . -68.0(8) ?
C14A N2 C11 C12 . . . . 178.7(6) ?

_cod_database_fobs_code 2243466
