#------------------------------------------------------------------------------
#$Date: 2021-01-09 08:07:14 +0200 (Sat, 09 Jan 2021) $
#$Revision: 260886 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243722.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_2243722
loop_
_publ_author_name
'Pham, Duyen N. K.'
'Chadeayne, Andrew R.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 Psilacetin derivatives: fumarate salts of the methyl--ethyl,
 methyl--allyl and diallyl variants of the psilocin prodrug
;
_journal_coeditor_code           HB7959
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              101
_journal_page_last               106
_journal_paper_doi               10.1107/S2056989021000116
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C16 H21 N2 O2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C16 H21 N2 O2 +, C4 H3 O4 -'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41
_chemical_name_systematic
;
[2-(4-Acetyloxy-1H-indol-3-yl)ethyl](methyl)prop-2-enylazanium
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 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.394(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9702(4)
_cell_length_b                   14.1788(7)
_cell_length_c                   9.8035(5)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.68
_cell_volume                     1016.80(9)
_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 0.984
_diffrn_measured_fraction_theta_max 0.985
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26393
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.709
_diffrn_reflns_theta_min         2.785
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.164
_refine_ls_abs_structure_details
;
Flack x determined using 1577 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0425
_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)+(0.0592P)²+0.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                3516
_reflns_number_total             3797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7959sup1.cif
_cod_data_source_block           II
_cod_database_code               2243722
_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   0.969
_shelx_estimated_absorpt_t_max   0.981
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 0.0798(3) 0.7896(2) 0.2116(3) 0.0688(8) Uani d 1 . .
O O2 -0.0241(3) 0.69624(16) 0.3445(2) 0.0496(5) Uani d 1 . .
O O3 0.5149(3) 0.4747(3) 0.3619(3) 0.0834(11) Uani d 1 . .
O O4 0.5188(3) 0.4841(3) 0.5856(3) 0.0701(8) Uani d 1 . .
H H4A 0.397(2) 0.484(4) 0.543(5) 0.105 Uiso d 1 . .
O O5 1.1781(3) 0.53485(19) 0.6822(2) 0.0559(6) Uani d 1 . .
O O6 1.1837(2) 0.47635(18) 0.4735(2) 0.0493(5) Uani d 1 . .
N N1 -0.4734(4) 0.5921(2) -0.1031(3) 0.0585(8) Uani d 1 . .
H H1 -0.577(3) 0.580(3) -0.176(3) 0.070 Uiso d 1 . .
N N2 0.2259(4) 0.4086(2) 0.1361(3) 0.0499(6) Uani d 1 . .
H H2 0.297(4) 0.436(3) 0.221(3) 0.060 Uiso d 1 . .
C C1 0.2902(5) 0.7280(3) 0.4444(5) 0.0754(12) Uani d 1 . .
H H1A 0.377223 0.771990 0.436158 0.113 Uiso calc 1 . .
H H1B 0.330726 0.664822 0.439678 0.113 Uiso calc 1 . .
H H1C 0.279217 0.737271 0.537570 0.113 Uiso calc 1 . .
C C2 0.1079(5) 0.7436(2) 0.3193(4) 0.0506(8) Uani d 1 . .
C C3 -0.2038(4) 0.7039(2) 0.2363(3) 0.0464(7) Uani d 1 . .
C C4 -0.3218(6) 0.7650(3) 0.2617(5) 0.0642(9) Uani d 1 . .
H H4 -0.281087 0.803090 0.345811 0.077 Uiso calc 1 . .
C C5 -0.5046(6) 0.7694(3) 0.1595(6) 0.0776(12) Uani d 1 . .
H H5 -0.584090 0.810842 0.177293 0.093 Uiso calc 1 . .
C C6 -0.5689(5) 0.7147(3) 0.0352(5) 0.0685(11) Uani d 1 . .
H H6 -0.690394 0.718337 -0.031497 0.082 Uiso calc 1 . .
C C7 -0.4473(4) 0.6531(2) 0.0109(4) 0.0494(8) Uani d 1 . .
C C8 -0.2618(4) 0.6455(2) 0.1114(3) 0.0401(6) Uani d 1 . .
C C9 -0.1793(4) 0.5762(2) 0.0515(3) 0.0418(6) Uani d 1 . .
C C10 -0.3140(5) 0.5459(3) -0.0778(3) 0.0531(8) Uani d 1 . .
H H10 -0.299037 0.500150 -0.139982 0.064 Uiso calc 1 . .
C C11 0.0171(4) 0.5439(2) 0.1121(4) 0.0491(7) Uani d 1 . .
H H11A 0.082400 0.578146 0.062769 0.059 Uiso calc 1 . .
H H11B 0.074142 0.558138 0.217389 0.059 Uiso calc 1 . .
C C12 0.0315(4) 0.4409(2) 0.0897(4) 0.0554(8) Uani d 1 . .
H H12A -0.036085 0.425881 -0.014403 0.066 Uiso calc 1 . .
H H12B -0.024264 0.406630 0.146635 0.066 Uiso calc 1 . .
C C13 0.2451(6) 0.3047(3) 0.1669(5) 0.0656(10) Uani d 1 . .
H H13A 0.165728 0.271014 0.078805 0.079 Uiso calc 1 . .
H H13B 0.369974 0.285978 0.188000 0.079 Uiso calc 1 . .
C C14 0.1994(6) 0.2777(3) 0.2918(5) 0.0745(11) Uani d 1 . .
H H14 0.260747 0.308976 0.381312 0.089 Uiso calc 1 . .
C C15 0.0818(9) 0.2144(4) 0.2897(8) 0.1105(19) Uani d 1 . .
H H15A 0.017104 0.181308 0.202624 0.133 Uiso calc 1 . .
H H15B 0.061757 0.201983 0.375131 0.133 Uiso calc 1 . .
C C16 0.3019(6) 0.4354(4) 0.0257(4) 0.0741(12) Uani d 1 . .
H H16A 0.425726 0.413518 0.058781 0.111 Uiso calc 1 . .
H H16B 0.299241 0.502755 0.015387 0.111 Uiso calc 1 . .
H H16C 0.229752 0.407199 -0.068548 0.111 Uiso calc 1 . .
C C17 0.5946(3) 0.4843(2) 0.4951(3) 0.0412(6) Uani d 1 . .
C C18 0.7971(3) 0.4950(2) 0.5624(3) 0.0418(6) Uani d 1 . .
H H18 0.853754 0.504450 0.664454 0.050 Uiso calc 1 . .
C C19 0.8996(3) 0.4919(2) 0.4870(3) 0.0406(6) Uani d 1 . .
H H19 0.844150 0.482380 0.384840 0.049 Uiso calc 1 . .
C C20 1.1021(3) 0.5030(2) 0.5574(3) 0.0372(6) 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
C2 O2 C3 . . 117.2(2) ?
C17 O4 H4A . . 114(3) ?
C7 N1 H1 . . 126(3) ?
C7 N1 C10 . . 109.2(3) ?
C10 N1 H1 . . 124(3) ?
C12 N2 H2 . . 110(3) ?
C13 N2 H2 . . 105(3) ?
C13 N2 C12 . . 111.8(3) ?
C16 N2 H2 . . 106(3) ?
C16 N2 C12 . . 111.8(3) ?
C16 N2 C13 . . 111.1(3) ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
O1 C2 O2 . . 123.5(3) ?
O1 C2 C1 . . 126.1(3) ?
O2 C2 C1 . . 110.4(3) ?
C4 C3 O2 . . 118.5(3) ?
C4 C3 C8 . . 121.4(3) ?
C8 C3 O2 . . 119.9(3) ?
C3 C4 H4 . . 120.3 ?
C3 C4 C5 . . 119.4(4) ?
C5 C4 H4 . . 120.3 ?
C4 C5 H5 . . 119.0 ?
C6 C5 C4 . . 121.9(4) ?
C6 C5 H5 . . 119.0 ?
C5 C6 H6 . . 121.0 ?
C5 C6 C7 . . 118.0(3) ?
C7 C6 H6 . . 121.0 ?
N1 C7 C6 . . 130.4(3) ?
N1 C7 C8 . . 107.4(3) ?
C6 C7 C8 . . 122.2(3) ?
C3 C8 C7 . . 117.0(3) ?
C3 C8 C9 . . 136.1(3) ?
C7 C8 C9 . . 106.8(3) ?
C8 C9 C11 . . 128.4(3) ?
C10 C9 C8 . . 106.1(3) ?
C10 C9 C11 . . 125.5(3) ?
N1 C10 C9 . . 110.5(3) ?
N1 C10 H10 . . 124.7 ?
C9 C10 H10 . . 124.7 ?
C9 C11 H11A . . 109.3 ?
C9 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C12 C11 C9 . . 111.7(3) ?
C12 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
N2 C12 H12A . . 109.1 ?
N2 C12 H12B . . 109.1 ?
C11 C12 N2 . . 112.7(3) ?
C11 C12 H12A . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
N2 C13 H13A . . 109.0 ?
N2 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C14 C13 N2 . . 112.8(3) ?
C14 C13 H13A . . 109.0 ?
C14 C13 H13B . . 109.0 ?
C13 C14 H14 . . 116.9 ?
C15 C14 C13 . . 126.1(5) ?
C15 C14 H14 . . 116.9 ?
C14 C15 H15A . . 120.0 ?
C14 C15 H15B . . 120.0 ?
H15A C15 H15B . . 120.0 ?
N2 C16 H16A . . 109.5 ?
N2 C16 H16B . . 109.5 ?
N2 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 O4 . . 124.6(2) ?
O3 C17 C18 . . 120.1(2) ?
O4 C17 C18 . . 115.3(2) ?
C17 C18 H18 . . 118.0 ?
C19 C18 C17 . . 124.0(2) ?
C19 C18 H18 . . 118.0 ?
C18 C19 H19 . . 118.6 ?
C18 C19 C20 . . 122.8(2) ?
C20 C19 H19 . . 118.6 ?
O5 C20 O6 . . 125.1(2) ?
O5 C20 C19 . . 121.3(2) ?
O6 C20 C19 . . 113.6(2) ?
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 C2 . 1.185(4) ?
O2 C2 . 1.351(4) ?
O2 C3 . 1.408(4) ?
O3 C17 . 1.212(3) ?
O4 H4A . 0.894(14) ?
O4 C17 . 1.256(3) ?
O5 C20 . 1.216(3) ?
O6 C20 . 1.290(3) ?
N1 H1 . 0.867(14) ?
N1 C7 . 1.362(5) ?
N1 C10 . 1.362(5) ?
N2 H2 . 0.890(14) ?
N2 C12 . 1.502(4) ?
N2 C13 . 1.499(5) ?
N2 C16 . 1.484(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 C2 . 1.499(5) ?
C3 C4 . 1.372(5) ?
C3 C8 . 1.396(4) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.404(6) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.361(7) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.394(6) ?
C7 C8 . 1.419(4) ?
C8 C9 . 1.431(5) ?
C9 C10 . 1.365(4) ?
C9 C11 . 1.508(4) ?
C10 H10 . 0.9300 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C11 C12 . 1.488(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C13 C14 . 1.460(6) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.292(7) ?
C15 H15A . 0.9300 ?
C15 H15B . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.489(3) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.302(4) ?
C19 H19 . 0.9300 ?
C19 C20 . 1.491(3) ?
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 O5 1_354 0.867(14) 2.000(17) 2.857(3) 169(4) yes
O4 H4A O6 1_455 0.894(14) 1.562(15) 2.454(3) 175(6) 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
O2 C3 C4 C5 . . . . -176.1(3) ?
O2 C3 C8 C7 . . . . 176.5(2) ?
O2 C3 C8 C9 . . . . -4.7(5) ?
O3 C17 C18 C19 . . . . -2.3(6) ?
O4 C17 C18 C19 . . . . 176.4(4) ?
N1 C7 C8 C3 . . . . 178.7(3) ?
N1 C7 C8 C9 . . . . -0.4(3) ?
N2 C13 C14 C15 . . . . 125.8(5) ?
C2 O2 C3 C4 . . . . -100.4(3) ?
C2 O2 C3 C8 . . . . 83.9(4) ?
C3 O2 C2 O1 . . . . -0.7(5) ?
C3 O2 C2 C1 . . . . -180.0(3) ?
C3 C4 C5 C6 . . . . -0.1(6) ?
C3 C8 C9 C10 . . . . -179.0(3) ?
C3 C8 C9 C11 . . . . -1.1(6) ?
C4 C3 C8 C7 . . . . 0.9(5) ?
C4 C3 C8 C9 . . . . 179.7(3) ?
C4 C5 C6 C7 . . . . 0.0(6) ?
C5 C6 C7 N1 . . . . -179.0(4) ?
C5 C6 C7 C8 . . . . 0.5(5) ?
C6 C7 C8 C3 . . . . -1.0(4) ?
C6 C7 C8 C9 . . . . 179.9(3) ?
C7 N1 C10 C9 . . . . -0.9(4) ?
C7 C8 C9 C10 . . . . -0.1(3) ?
C7 C8 C9 C11 . . . . 177.7(3) ?
C8 C3 C4 C5 . . . . -0.4(5) ?
C8 C9 C10 N1 . . . . 0.6(4) ?
C8 C9 C11 C12 . . . . 142.7(3) ?
C9 C11 C12 N2 . . . . 174.6(3) ?
C10 N1 C7 C6 . . . . -179.6(4) ?
C10 N1 C7 C8 . . . . 0.8(4) ?
C10 C9 C11 C12 . . . . -39.8(4) ?
C11 C9 C10 N1 . . . . -177.3(3) ?
C12 N2 C13 C14 . . . . -63.6(4) ?
C13 N2 C12 C11 . . . . 158.9(3) ?
C16 N2 C12 C11 . . . . -75.8(4) ?
C16 N2 C13 C14 . . . . 170.7(3) ?
C17 C18 C19 C20 . . . . 179.9(3) ?
C18 C19 C20 O5 . . . . -15.6(5) ?
C18 C19 C20 O6 . . . . 164.6(3) ?

_cod_database_fobs_code 2243722
