#------------------------------------------------------------------------------
#$Date: 2020-03-28 08:19:52 +0200 (Sat, 28 Mar 2020) $
#$Revision: 249820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243331.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_2243331
loop_
_publ_author_name
'Chadeayne, Andrew R.'
'Pham, Duyen N. K.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 Norpsilocin: freebase and fumarate salt
;
_journal_coeditor_code           PK2623
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              589
_journal_page_last               593
_journal_paper_doi               10.1107/S2056989020004077
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C11 H15 N2 O +, 0.5C4 H2 O4 2-'
_chemical_formula_moiety         'C11 H15 N2 O +, 0.5(C4 H2 O4 2-)'
_chemical_formula_sum            'C13 H16 N2 O3'
_chemical_formula_weight         248.28
_chemical_name_common
;
4-Hydroxy-N-methyltryptammonium fumarate
;
_chemical_name_systematic
;
Bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]methylazanium}
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
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                105.524(4)
_cell_angle_beta                 110.554(4)
_cell_angle_gamma                97.167(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7363(10)
_cell_length_b                   9.7146(12)
_cell_length_c                   9.7854(13)
_cell_measurement_reflns_used    3848
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.66
_cell_volume                     643.69(15)
_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 0.995
_diffrn_measured_fraction_theta_max 0.989
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0289
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.463
_diffrn_reflns_theta_min         2.655
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.147
_refine_ls_extinction_coef       0.035(8)
_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   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0391
_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)+(0.0428P)²+0.1031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                1774
_reflns_number_total             2365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2623sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        643.69(14)
_cod_database_code               2243331
_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   0.978
_shelx_estimated_absorpt_t_max   0.997
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 O1 0.71021(18) 0.24171(13) 0.73074(16) 0.0516(4) Uani d 1 . .
N N1 1.1025(2) 0.68290(16) 0.82025(18) 0.0458(4) Uani d 1 . .
N N2 1.1755(2) 0.13836(16) 0.45820(17) 0.0390(4) Uani d 1 . .
C C1 0.9034(2) 0.47406(17) 0.77976(18) 0.0351(4) Uani d 1 . .
C C2 0.7537(2) 0.39203(18) 0.79685(19) 0.0391(4) Uani d 1 . .
C C3 0.6597(3) 0.4650(2) 0.8775(2) 0.0492(5) Uani d 1 . .
H H3 0.559823 0.411333 0.888131 0.059 Uiso calc 1 . .
C C4 0.7117(3) 0.6188(2) 0.9441(2) 0.0532(5) Uani d 1 . .
H H4 0.644580 0.664964 0.997328 0.064 Uiso calc 1 . .
C C5 0.8583(3) 0.7030(2) 0.9328(2) 0.0480(5) Uani d 1 . .
H H5 0.893452 0.804937 0.978251 0.058 Uiso calc 1 . .
C C6 0.9524(2) 0.62851(18) 0.85004(19) 0.0391(4) Uani d 1 . .
C C7 1.1455(3) 0.56779(19) 0.7313(2) 0.0444(4) Uani d 1 . .
H H7 1.240746 0.577663 0.694858 0.053 Uiso calc 1 . .
C C8 1.0291(2) 0.43736(18) 0.70422(19) 0.0379(4) Uani d 1 . .
C C9 1.0327(3) 0.28658(18) 0.6159(2) 0.0434(4) Uani d 1 . .
H H9A 0.906459 0.236367 0.536418 0.052 Uiso calc 1 . .
H H9B 1.066169 0.230581 0.685761 0.052 Uiso calc 1 . .
C C10 1.1729(2) 0.29082(18) 0.5407(2) 0.0398(4) Uani d 1 . .
H H10A 1.137504 0.343594 0.467796 0.048 Uiso calc 1 . .
H H10B 1.299028 0.342809 0.619295 0.048 Uiso calc 1 . .
C C11 1.3055(3) 0.1317(2) 0.3774(2) 0.0561(5) Uani d 1 . .
H H11A 1.293563 0.030805 0.321818 0.084 Uiso calc 1 . .
H H11B 1.434183 0.174879 0.451983 0.084 Uiso calc 1 . .
H H11C 1.273049 0.184976 0.306086 0.084 Uiso calc 1 . .
C C12 0.3434(2) 0.02114(16) 0.80503(17) 0.0311(4) Uani d 1 . .
C C13 0.5073(2) 0.01566(17) 0.94080(18) 0.0344(4) Uani d 1 . .
H H13 0.628166 0.035974 0.941097 0.041 Uiso calc 1 . .
O O2 0.17836(15) -0.03196(13) 0.78734(13) 0.0423(3) Uani d 1 . .
O O3 0.38449(16) 0.07932(13) 0.71675(14) 0.0461(3) Uani d 1 . .
H H1 0.613(2) 0.203(2) 0.745(3) 0.074(7) Uiso d 1 . .
H H1A 1.141(3) 0.7760(12) 0.839(2) 0.069(7) Uiso d 1 . .
H H2A 1.216(3) 0.0955(19) 0.5298(18) 0.054(6) Uiso d 1 . .
H H2B 1.0586(16) 0.0926(19) 0.3889(18) 0.054(6) Uiso 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 O1 H1 . . 109.6(15) ?
C6 N1 C7 . . 108.98(14) ?
C6 N1 H1A . . 121.5(15) ?
C7 N1 H1A . . 128.2(15) ?
C10 N2 H2A . . 106.9(13) ?
C10 N2 H2B . . 107.9(13) ?
C11 N2 C10 . . 114.20(14) ?
C11 N2 H2A . . 107.5(13) ?
C11 N2 H2B . . 108.4(13) ?
H2A N2 H2B . . 112.1(18) ?
C2 C1 C6 . . 117.87(15) ?
C2 C1 C8 . . 134.53(15) ?
C6 C1 C8 . . 107.60(14) ?
O1 C2 C1 . . 117.25(15) ?
O1 C2 C3 . . 123.67(15) ?
C3 C2 C1 . . 119.08(16) ?
C2 C3 H3 . . 119.4 ?
C2 C3 C4 . . 121.20(17) ?
C4 C3 H3 . . 119.4 ?
C3 C4 H4 . . 119.1 ?
C5 C4 C3 . . 121.82(18) ?
C5 C4 H4 . . 119.1 ?
C4 C5 H5 . . 121.6 ?
C4 C5 C6 . . 116.76(17) ?
C6 C5 H5 . . 121.6 ?
N1 C6 C1 . . 107.08(15) ?
N1 C6 C5 . . 129.66(16) ?
C5 C6 C1 . . 123.26(16) ?
N1 C7 H7 . . 124.7 ?
C8 C7 N1 . . 110.51(15) ?
C8 C7 H7 . . 124.7 ?
C1 C8 C9 . . 127.04(14) ?
C7 C8 C1 . . 105.81(15) ?
C7 C8 C9 . . 127.14(16) ?
C8 C9 H9A . . 109.1 ?
C8 C9 H9B . . 109.1 ?
C8 C9 C10 . . 112.38(13) ?
H9A C9 H9B . . 107.9 ?
C10 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
N2 C10 C9 . . 110.39(13) ?
N2 C10 H10A . . 109.6 ?
N2 C10 H10B . . 109.6 ?
C9 C10 H10A . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C13 . . 118.55(13) ?
O2 C12 O3 . . 124.96(14) ?
O3 C12 C13 . . 116.49(14) ?
C12 C13 H13 . . 117.6 ?
C13 C13 C12 2_657 . 124.77(19) ?
C13 C13 H13 2_657 . 117.6 ?
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 . 1.372(2) ?
O1 H1 . 0.870(10) ?
N1 C6 . 1.372(2) ?
N1 C7 . 1.376(2) ?
N1 H1A . 0.863(10) ?
N2 C10 . 1.492(2) ?
N2 C11 . 1.479(2) ?
N2 H2A . 0.892(9) ?
N2 H2B . 0.885(9) ?
C1 C2 . 1.408(2) ?
C1 C6 . 1.411(2) ?
C1 C8 . 1.438(2) ?
C2 C3 . 1.373(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.402(3) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.368(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.393(3) ?
C7 H7 . 0.9300 ?
C7 C8 . 1.362(2) ?
C8 C9 . 1.498(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.511(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.499(2) ?
C12 O2 . 1.2488(18) ?
C12 O3 . 1.2553(18) ?
C13 C13 2_657 1.311(3) ?
C13 H13 . 0.9300 ?
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
O1 H1 O3 . 0.870(10) 1.894(12) 2.7399(16) 163(2) yes
N1 H1A O2 1_665 0.863(10) 2.073(12) 2.8854(18) 157(2) yes
N2 H2A O3 1_655 0.892(9) 1.899(12) 2.7349(18) 155.3(18) yes
N2 H2B O2 2_656 0.885(9) 1.910(11) 2.7715(19) 164.0(18) 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 C2 C3 C4 . . . . 179.30(17) ?
N1 C7 C8 C1 . . . . 0.79(19) ?
N1 C7 C8 C9 . . . . -178.45(16) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C1 C8 C9 C10 . . . . 175.12(15) ?
C2 C1 C6 N1 . . . . 178.79(14) ?
C2 C1 C6 C5 . . . . -1.0(2) ?
C2 C1 C8 C7 . . . . -179.45(18) ?
C2 C1 C8 C9 . . . . -0.2(3) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 N1 . . . . -179.84(17) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
C6 N1 C7 C8 . . . . -1.3(2) ?
C6 C1 C2 O1 . . . . -178.63(14) ?
C6 C1 C2 C3 . . . . 1.4(2) ?
C6 C1 C8 C7 . . . . -0.02(18) ?
C6 C1 C8 C9 . . . . 179.22(16) ?
C7 N1 C6 C1 . . . . 1.23(18) ?
C7 N1 C6 C5 . . . . -179.00(18) ?
C7 C8 C9 C10 . . . . -5.8(3) ?
C8 C1 C2 O1 . . . . 0.7(3) ?
C8 C1 C2 C3 . . . . -179.26(18) ?
C8 C1 C6 N1 . . . . -0.74(18) ?
C8 C1 C6 C5 . . . . 179.47(16) ?
C8 C9 C10 N2 . . . . 178.34(14) ?
C11 N2 C10 C9 . . . . 178.49(15) ?
O2 C12 C13 C13 . . . 2_657 -13.3(3) ?
O3 C12 C13 C13 . . . 2_657 167.0(2) ?

_cod_database_fobs_code 2243331
