#------------------------------------------------------------------------------
#$Date: 2021-09-11 05:00:10 +0300 (Sat, 11 Sep 2021) $
#$Revision: 269100 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022457.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_2022457
loop_
_publ_author_name
'Pham, Duyen N. K.'
'Belanger, Zachary S.'
'Chadeayne, Andrew R.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 The crystalline forms of nine hydrochloride salts of substituted
 tryptamines
;
_journal_coeditor_code           YP3219
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621008950
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C10 H12 F N2 +, Cl -'
_chemical_formula_moiety         'C10 H12 F N2 +, Cl -'
_chemical_formula_sum            'C10 H12 Cl F N2'
_chemical_formula_weight         214.67
_chemical_name_common
;
5-Fluorotryptammonium chloride
;
_chemical_name_systematic
;
2-(5-Fluoro-1H-indol-3-yl)ethan-1-aminium chloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6708(4)
_cell_length_b                   9.6684(5)
_cell_length_c                   25.6854(12)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.83
_cell_volume                     2153.28(18)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0428
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            65854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.834
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0411
_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)+(0.0348P)²+1.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1904
_reflns_number_total             2190
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3219sup1.cif
_cod_data_source_block           6
_cod_database_code               2022457
_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   0.910
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
Cl Cl1 0.31363(6) 0.14447(5) 0.46647(2) 0.05314(17) Uani d 1 . .
F F1 0.64999(17) 0.44187(18) 0.79095(5) 0.0866(5) Uani d 1 . .
N N1 0.5244(2) 0.59702(19) 0.59246(7) 0.0577(5) Uani d 1 . .
N N2 0.5407(2) 0.14363(17) 0.56311(7) 0.0480(4) Uani d 1 . .
C C1 0.4366(2) 0.4880(2) 0.57683(8) 0.0539(5) Uani d 1 . .
H H1A 0.393075 0.478901 0.543916 0.065 Uiso calc 1 . .
C C2 0.5701(2) 0.57566(19) 0.64294(8) 0.0489(5) Uani d 1 . .
C C3 0.6599(2) 0.6567(2) 0.67575(11) 0.0644(6) Uani d 1 . .
H H3 0.699807 0.740928 0.664589 0.077 Uiso calc 1 . .
C C4 0.6878(3) 0.6086(3) 0.72517(10) 0.0672(6) Uani d 1 . .
H H4 0.749892 0.658979 0.747816 0.081 Uiso calc 1 . .
C C5 0.6228(2) 0.4845(2) 0.74111(8) 0.0581(5) Uani d 1 . .
C C6 0.5326(2) 0.4029(2) 0.71029(7) 0.0485(4) Uani d 1 . .
H H6 0.490343 0.320759 0.722616 0.058 Uiso calc 1 . .
C C7 0.50647(19) 0.44837(18) 0.65919(7) 0.0409(4) Uani d 1 . .
C C8 0.4211(2) 0.3940(2) 0.61609(7) 0.0447(4) Uani d 1 . .
C C9 0.3376(2) 0.2586(2) 0.61418(8) 0.0548(5) Uani d 1 . .
H H9A 0.269263 0.258239 0.584276 0.066 Uiso calc 1 . .
H H9B 0.274446 0.249609 0.645168 0.066 Uiso calc 1 . .
C C10 0.4442(2) 0.1354(2) 0.61067(7) 0.0526(5) Uani d 1 . .
H H10A 0.510083 0.132699 0.641169 0.063 Uiso calc 1 . .
H H10B 0.383771 0.051022 0.609957 0.063 Uiso calc 1 . .
H H2A 0.476(2) 0.154(2) 0.5320(6) 0.077(8) Uiso d 1 . .
H H2B 0.605(2) 0.0613(17) 0.5590(9) 0.076(7) Uiso d 1 . .
H H2C 0.609(2) 0.2241(16) 0.5622(9) 0.067(6) Uiso d 1 . .
H H1 0.554(3) 0.6645(19) 0.5727(9) 0.085(9) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
C1 N1 C2 . . 108.90(17) ?
C1 N1 H1 . . 125.1(18) ?
C2 N1 H1 . . 125.7(18) ?
C10 N2 H2A . . 110.5(14) ?
C10 N2 H2B . . 111.6(14) ?
C10 N2 H2C . . 113.7(13) ?
H2A N2 H2B . . 109(2) ?
H2A N2 H2C . . 104.4(19) ?
H2B N2 H2C . . 107.5(19) ?
N1 C1 H1A . . 124.7 ?
N1 C1 C8 . . 110.67(18) ?
C8 C1 H1A . . 124.7 ?
N1 C2 C3 . . 130.6(2) ?
N1 C2 C7 . . 107.33(17) ?
C3 C2 C7 . . 122.1(2) ?
C2 C3 H3 . . 121.0 ?
C4 C3 C2 . . 117.9(2) ?
C4 C3 H3 . . 121.0 ?
C3 C4 H4 . . 120.2 ?
C3 C4 C5 . . 119.6(2) ?
C5 C4 H4 . . 120.2 ?
F1 C5 C4 . . 117.9(2) ?
C6 C5 F1 . . 117.9(2) ?
C6 C5 C4 . . 124.2(2) ?
C5 C6 H6 . . 121.5 ?
C5 C6 C7 . . 117.01(19) ?
C7 C6 H6 . . 121.5 ?
C2 C7 C8 . . 107.07(16) ?
C6 C7 C2 . . 119.13(17) ?
C6 C7 C8 . . 133.79(18) ?
C1 C8 C7 . . 106.03(17) ?
C1 C8 C9 . . 127.31(18) ?
C7 C8 C9 . . 126.62(17) ?
C8 C9 H9A . . 108.9 ?
C8 C9 H9B . . 108.9 ?
C8 C9 C10 . . 113.29(15) ?
H9A C9 H9B . . 107.7 ?
C10 C9 H9A . . 108.9 ?
C10 C9 H9B . . 108.9 ?
N2 C10 C9 . . 110.65(16) ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
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
F1 C5 . 1.365(2) ?
N1 C1 . 1.361(3) ?
N1 C2 . 1.371(3) ?
N1 H1 . 0.863(10) ?
N2 C10 . 1.483(3) ?
N2 H2A . 0.983(10) ?
N2 H2B . 0.980(10) ?
N2 H2C . 0.976(10) ?
C1 H1A . 0.9300 ?
C1 C8 . 1.364(3) ?
C2 C3 . 1.389(3) ?
C2 C7 . 1.412(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.373(3) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.388(3) ?
C5 C6 . 1.364(3) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.403(3) ?
C7 C8 . 1.432(2) ?
C8 C9 . 1.497(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.510(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
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
N2 H2A Cl1 . 0.983(10) 2.194(11) 3.1685(18) 171(2) yes
N2 H2B Cl1 5_656 0.980(10) 2.209(12) 3.1513(17) 161(2) yes
N2 H2C Cl1 4_556 0.976(10) 2.306(13) 3.2208(17) 155.7(18) yes
N1 H1 Cl1 5_666 0.863(10) 2.398(12) 3.2418(18) 166(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
F1 C5 C6 C7 . . . . -179.84(16) ?
N1 C1 C8 C7 . . . . -0.3(2) ?
N1 C1 C8 C9 . . . . -178.08(17) ?
N1 C2 C3 C4 . . . . -179.9(2) ?
N1 C2 C7 C6 . . . . -178.49(16) ?
N1 C2 C7 C8 . . . . 0.26(19) ?
C1 N1 C2 C3 . . . . -179.83(19) ?
C1 N1 C2 C7 . . . . -0.5(2) ?
C1 C8 C9 C10 . . . . 104.4(2) ?
C2 N1 C1 C8 . . . . 0.5(2) ?
C2 C3 C4 C5 . . . . -1.9(3) ?
C2 C7 C8 C1 . . . . 0.04(19) ?
C2 C7 C8 C9 . . . . 177.80(17) ?
C3 C2 C7 C6 . . . . 0.9(3) ?
C3 C2 C7 C8 . . . . 179.69(17) ?
C3 C4 C5 F1 . . . . -178.34(19) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . 0.7(3) ?
C5 C6 C7 C2 . . . . -1.7(2) ?
C5 C6 C7 C8 . . . . 179.99(18) ?
C6 C7 C8 C1 . . . . 178.53(19) ?
C6 C7 C8 C9 . . . . -3.7(3) ?
C7 C2 C3 C4 . . . . 0.9(3) ?
C7 C8 C9 C10 . . . . -72.9(2) ?
C8 C9 C10 N2 . . . . -59.8(2) ?

_cod_database_fobs_code 2022457
