#------------------------------------------------------------------------------
#$Date: 2021-03-20 08:14:24 +0200 (Sat, 20 Mar 2021) $
#$Revision: 263206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243786.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_2243786
loop_
_publ_author_name
'Pham, Duyen N. K.'
'Sammeta, Vamshikrishna Reddy'
'Chadeayne, Andrew R.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 `Foxtrot' fumarate: a water-soluble salt of
 N,N-diallyl-5-methoxytryptamine (5-MeO-DALT)
;
_journal_coeditor_code           EY2005
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              416
_journal_page_last               419
_journal_paper_doi               10.1107/S2056989021002838
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C17 H23 N2 O +, 0.5C4 H2 O4 2-'
_chemical_formula_moiety         'C17 H23 N2 O +, 0.5(C4 H2 O4 2-)'
_chemical_formula_sum            'C19 H24 N2 O3'
_chemical_formula_weight         328.40
_chemical_name_common
;
Bis(N,N-diallyl-5-methoxytryptammonium) fumarate
;
_chemical_name_systematic
;
Bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-
N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                108.081(3)
_cell_angle_beta                 104.365(3)
_cell_angle_gamma                95.903(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8791(7)
_cell_length_b                   9.2908(7)
_cell_length_c                   13.5352(11)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.72
_cell_volume                     894.87(13)
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.722
_diffrn_reflns_theta_min         2.721
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2788
_reflns_number_total             3383
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ey2005sup1.cif
_cod_data_source_block           I
_cod_database_code               2243786
_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   0.972
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 O3 0.32558(15) 0.59832(14) 0.09859(10) 0.0582(3) Uani d 1 . .
O O2 0.21841(18) 0.81313(14) 0.10656(11) 0.0675(4) Uani d 1 . .
O O1 0.7398(2) 0.32650(13) 0.56660(10) 0.0647(4) Uani d 1 . .
N N1 0.7725(2) 0.95161(15) 0.70532(10) 0.0491(3) Uani d 1 . .
H H1 0.773(2) 1.0212(17) 0.7654(10) 0.058(5) Uiso d 1 . .
N N2 0.63718(16) 0.74775(14) 0.22313(9) 0.0392(3) Uani d 1 . .
H H2 0.5248(15) 0.704(2) 0.1812(15) 0.078(6) Uiso d 1 . .
C C1 0.77565(19) 0.72996(16) 0.57820(11) 0.0372(3) Uani d 1 . .
C C2 0.7682(2) 0.57053(17) 0.53501(11) 0.0412(3) Uani d 1 . .
H H2A 0.774806 0.524400 0.464848 0.049 Uiso calc 1 . .
C C3 0.7507(2) 0.48447(17) 0.59951(12) 0.0453(4) Uani d 1 . .
C C4 0.7447(2) 0.55271(19) 0.70629(13) 0.0503(4) Uani d 1 . .
H H4 0.735505 0.491381 0.748234 0.060 Uiso calc 1 . .
C C5 0.7522(2) 0.70801(19) 0.74980(12) 0.0494(4) Uani d 1 . .
H H5 0.747839 0.753096 0.820581 0.059 Uiso calc 1 . .
C C6 0.7667(2) 0.79678(17) 0.68493(11) 0.0420(3) Uani d 1 . .
C C7 0.7879(2) 0.98335(18) 0.61541(12) 0.0460(4) Uani d 1 . .
H H7 0.795238 1.080810 0.609612 0.055 Uiso calc 1 . .
C C8 0.79099(19) 0.85197(16) 0.53544(11) 0.0386(3) Uani d 1 . .
C C9 0.80805(19) 0.83539(17) 0.42450(11) 0.0400(3) Uani d 1 . .
H H9A 0.894016 0.770455 0.409345 0.048 Uiso calc 1 . .
H H9B 0.852886 0.936130 0.423723 0.048 Uiso calc 1 . .
C C10 0.63041(19) 0.76520(17) 0.33583(11) 0.0386(3) Uani d 1 . .
H H10A 0.587159 0.664307 0.336960 0.046 Uiso calc 1 . .
H H10B 0.544568 0.829401 0.352776 0.046 Uiso calc 1 . .
C C11 0.7478(2) 0.63509(19) 0.18188(13) 0.0508(4) Uani d 1 . .
H H11A 0.750182 0.632850 0.110119 0.061 Uiso calc 1 . .
H H11B 0.869410 0.668790 0.229759 0.061 Uiso calc 1 . .
C C12 0.6761(3) 0.4763(2) 0.17570(15) 0.0624(5) Uani d 1 . .
H H12 0.555703 0.436157 0.138805 0.075 Uiso calc 1 . .
C C13 0.7660(4) 0.3904(3) 0.2168(2) 0.0886(7) Uani d 1 . .
H H13A 0.886868 0.425891 0.254358 0.106 Uiso calc 1 . .
H H13B 0.710420 0.292544 0.209010 0.106 Uiso calc 1 . .
C C14 0.6880(2) 0.90039(18) 0.21243(12) 0.0501(4) Uani d 1 . .
H H14A 0.623177 0.972370 0.248743 0.060 Uiso calc 1 . .
H H14B 0.814472 0.939713 0.249493 0.060 Uiso calc 1 . .
C C17 0.7066(3) 0.2475(2) 0.45399(15) 0.0660(5) Uani d 1 . .
H H17A 0.673648 0.138566 0.438067 0.099 Uiso calc 1 . .
H H17B 0.812447 0.268352 0.433750 0.099 Uiso calc 1 . .
H H17C 0.611040 0.282080 0.413694 0.099 Uiso calc 1 . .
C C15 0.6516(3) 0.8949(2) 0.09796(13) 0.0570(4) Uani d 1 . .
H H15 0.538880 0.845917 0.049925 0.068 Uiso calc 1 . .
C C16 0.7676(3) 0.9543(3) 0.06119(18) 0.0783(6) Uani d 1 . .
H H16A 0.881409 1.004033 0.107318 0.094 Uiso calc 1 . .
H H16B 0.737080 0.947286 -0.011317 0.094 Uiso calc 1 . .
C C19 0.02229(19) 0.57392(16) 0.00887(11) 0.0392(3) Uani d 1 . .
H H19 -0.063089 0.621325 -0.022769 0.047 Uiso calc 1 . .
C C18 0.2012(2) 0.67065(17) 0.07656(11) 0.0416(3) Uani d 1 . .
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
C3 O1 C17 . . 116.62(13) ?
C6 N1 H1 . . 127.5(13) ?
C7 N1 H1 . . 123.8(13) ?
C7 N1 C6 . . 108.60(12) ?
C10 N2 H2 . . 103.9(13) ?
C11 N2 H2 . . 105.0(13) ?
C11 N2 C10 . . 113.75(12) ?
C14 N2 H2 . . 109.2(13) ?
C14 N2 C10 . . 111.74(11) ?
C14 N2 C11 . . 112.46(13) ?
C2 C1 C6 . . 119.75(13) ?
C2 C1 C8 . . 133.20(13) ?
C6 C1 C8 . . 107.05(12) ?
C1 C2 H2A . . 121.0 ?
C3 C2 C1 . . 118.00(13) ?
C3 C2 H2A . . 121.0 ?
O1 C3 C4 . . 114.40(14) ?
C2 C3 O1 . . 123.88(14) ?
C2 C3 C4 . . 121.71(14) ?
C3 C4 H4 . . 119.5 ?
C5 C4 C3 . . 121.06(14) ?
C5 C4 H4 . . 119.5 ?
C4 C5 H5 . . 121.0 ?
C4 C5 C6 . . 118.05(14) ?
C6 C5 H5 . . 121.0 ?
N1 C6 C1 . . 107.68(13) ?
N1 C6 C5 . . 130.91(14) ?
C5 C6 C1 . . 121.41(14) ?
N1 C7 H7 . . 124.8 ?
C8 C7 N1 . . 110.47(14) ?
C8 C7 H7 . . 124.8 ?
C1 C8 C9 . . 125.93(13) ?
C7 C8 C1 . . 106.20(13) ?
C7 C8 C9 . . 127.88(14) ?
C8 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C8 C9 C10 . . 112.05(12) ?
H9A C9 H9B . . 107.9 ?
C10 C9 H9A . . 109.2 ?
C10 C9 H9B . . 109.2 ?
N2 C10 C9 . . 114.87(11) ?
N2 C10 H10A . . 108.6 ?
N2 C10 H10B . . 108.6 ?
C9 C10 H10A . . 108.6 ?
C9 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.5 ?
N2 C11 H11A . . 109.3 ?
N2 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C12 C11 N2 . . 111.77(14) ?
C12 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C11 C12 H12 . . 117.1 ?
C13 C12 C11 . . 125.7(2) ?
C13 C12 H12 . . 117.1 ?
C12 C13 H13A . . 120.0 ?
C12 C13 H13B . . 120.0 ?
H13A C13 H13B . . 120.0 ?
N2 C14 H14A . . 108.8 ?
N2 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.6 ?
C15 C14 N2 . . 114.01(13) ?
C15 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
O1 C17 H17A . . 109.5 ?
O1 C17 H17B . . 109.5 ?
O1 C17 H17C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C15 H15 . . 118.1 ?
C16 C15 C14 . . 123.87(18) ?
C16 C15 H15 . . 118.1 ?
C15 C16 H16A . . 120.0 ?
C15 C16 H16B . . 120.0 ?
H16A C16 H16B . . 120.0 ?
C19 C19 H19 2_565 . 118.0 ?
C19 C19 C18 2_565 . 124.09(18) ?
C18 C19 H19 . . 118.0 ?
O3 C18 C19 . . 116.27(13) ?
O2 C18 O3 . . 125.12(14) ?
O2 C18 C19 . . 118.62(15) ?
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
O3 C18 . 1.2709(19) ?
O2 C18 . 1.2400(19) ?
O1 C3 . 1.3817(19) ?
O1 C17 . 1.414(2) ?
N1 H1 . 0.865(9) ?
N1 C6 . 1.372(2) ?
N1 C7 . 1.368(2) ?
N2 H2 . 0.897(9) ?
N2 C10 . 1.4982(17) ?
N2 C11 . 1.494(2) ?
N2 C14 . 1.494(2) ?
C1 C2 . 1.402(2) ?
C1 C6 . 1.4073(19) ?
C1 C8 . 1.431(2) ?
C2 H2A . 0.9300 ?
C2 C3 . 1.375(2) ?
C3 C4 . 1.402(2) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.367(2) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.394(2) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.364(2) ?
C8 C9 . 1.5025(19) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.5224(19) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C11 C12 . 1.494(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.282(3) ?
C13 H13A . 0.9300 ?
C13 H13B . 0.9300 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 C15 . 1.488(2) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C15 H15 . 0.9300 ?
C15 C16 . 1.297(3) ?
C16 H16A . 0.9300 ?
C16 H16B . 0.9300 ?
C19 C19 2_565 1.312(3) ?
C19 H19 . 0.9300 ?
C19 C18 . 1.491(2) ?
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
N1 H1 O2 2_676 0.865(9) 1.909(10) 2.7729(17) 175.4(18) yes
N2 H2 O3 . 0.897(9) 1.677(10) 2.5669(16) 171(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 C3 C4 C5 . . . . -179.30(16) ?
N1 C7 C8 C1 . . . . 0.28(18) ?
N1 C7 C8 C9 . . . . -179.37(14) ?
N2 C11 C12 C13 . . . . -128.3(2) ?
N2 C14 C15 C16 . . . . -130.4(2) ?
C1 C2 C3 O1 . . . . 179.27(15) ?
C1 C2 C3 C4 . . . . -1.5(2) ?
C1 C8 C9 C10 . . . . 76.48(19) ?
C2 C1 C6 N1 . . . . -178.59(13) ?
C2 C1 C6 C5 . . . . 0.7(2) ?
C2 C1 C8 C7 . . . . 178.83(16) ?
C2 C1 C8 C9 . . . . -1.5(3) ?
C2 C3 C4 C5 . . . . 1.4(3) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C4 C5 C6 N1 . . . . 178.27(16) ?
C4 C5 C6 C1 . . . . -0.8(2) ?
C6 N1 C7 C8 . . . . 0.46(19) ?
C6 C1 C2 C3 . . . . 0.5(2) ?
C6 C1 C8 C7 . . . . -0.89(17) ?
C6 C1 C8 C9 . . . . 178.77(14) ?
C7 N1 C6 C1 . . . . -1.02(18) ?
C7 N1 C6 C5 . . . . 179.81(17) ?
C7 C8 C9 C10 . . . . -103.93(18) ?
C8 C1 C2 C3 . . . . -179.20(15) ?
C8 C1 C6 N1 . . . . 1.18(17) ?
C8 C1 C6 C5 . . . . -179.56(14) ?
C8 C9 C10 N2 . . . . 179.04(12) ?
C10 N2 C11 C12 . . . . 61.28(17) ?
C10 N2 C14 C15 . . . . -164.89(14) ?
C11 N2 C10 C9 . . . . 65.56(16) ?
C11 N2 C14 C15 . . . . 65.76(18) ?
C14 N2 C10 C9 . . . . -63.11(17) ?
C14 N2 C11 C12 . . . . -170.43(13) ?
C17 O1 C3 C2 . . . . -13.9(2) ?
C17 O1 C3 C4 . . . . 166.81(16) ?
C19 C19 C18 O3 2_565 . . . 14.9(3) ?
C19 C19 C18 O2 2_565 . . . -165.31(18) ?

_cod_database_fobs_code 2243786
