##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_journal_data_validation_number     ?
_journal_date_recd_electronic     2023-06-29
_journal_date_accepted     2023-07-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      8
_journal_page_first     752
_journal_page_last     756
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023006217
_journal_coeditor_code     TX2070
_publ_contact_author_name     'David R. Manke'
_publ_contact_author_address
;
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747
USA
;
_publ_contact_author_email     'dmanke@umassd.edu'
_publ_contact_author_fax     '(508)999-9167'
_publ_contact_author_phone     '(508)910-6554'
_publ_section_title
;
N-Cyclohexyltryptamine: freebase, bromide and fumarate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Naeem, Marilyn' .
;
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747
USA
;
    'Le, Alexander N.' .
;
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747
USA
;
    'Bauer, Barbara E.' .
;
CaaMTech, Inc.
58 East Sunset Way, Suite 209
Issaquah, WA 98027
USA
;
    'Chadeayne, Andrew R.' .
;
CaaMTech, Inc.
58 East Sunset Way, Suite 209
Issaquah, WA 98027
USA
;
    'Golen, James A.' .
;
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747
USA
;
    'Manke, David R.' .
;
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747
USA
;
_publ_section_synopsis
;
The crystal structure of the freebase of the monoalkyl tryptamine
N-cyclohexyltryptamine is presented, along with those of its bromide and
fumarate salts.
;
_chemical_name_systematic
;
N-[2-(1H-Indol-3-yl)ethyl]cyclohexanamine
;
_chemical_name_common
;
N-Cyclohexyltryptamine
;
_chemical_formula_moiety     'C16 H22 N2'
_chemical_formula_sum     'C16 H22 N2'
_chemical_formula_iupac     'C16 H22 N2'
_chemical_formula_weight     242.35
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21 1'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.5446(6)
_cell_length_b     10.3990(7)
_cell_length_c     8.6149(6)
_cell_angle_alpha     90
_cell_angle_beta     116.784(2)
_cell_angle_gamma     90
_cell_volume     683.35(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8705
_cell_measurement_theta_min     2.65
_cell_measurement_theta_max     25.75
_cell_measurement_temperature     297(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.178
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     264
_exptl_absorpt_coefficient_mu     0.069
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.6447
_exptl_absorpt_correction_T_max     0.7453
_diffrn_ambient_temperature     297.15
_diffrn_source     ?
_diffrn_source_power     1.5
_diffrn_source_voltage     50.0
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Venture CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18695
_diffrn_reflns_av_R_equivalents     0.0341
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_theta_min     3.295
_diffrn_reflns_theta_max     25.821
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     2621
_reflns_number_gt     2396
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0530
_refine_ls_R_factor_gt     0.0476
_refine_ls_wR_factor_gt     0.1185
_refine_ls_wR_factor_ref     0.1237
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     2621
_refine_ls_number_parameters     171
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0573P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.259
_refine_diff_density_min     -0.156
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1039 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     0.5(7)
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'
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    N N1 0.6840(4) 0.3201(3) 0.7683(3) 0.0574(6) Uani d 1 . .
    N N2 0.4242(4) 0.5812(3) 0.0943(3) 0.0632(7) Uani d 1 . .
    C C1 0.6257(4) 0.3382(4) 0.5918(4) 0.0653(9) Uani d 1 . .
    H H1A 0.570884 0.275362 0.507790 0.078 Uiso calc 1 . .
    C C2 0.7549(4) 0.4345(3) 0.8487(4) 0.0512(7) Uani d 1 . .
    C C3 0.8321(4) 0.4672(3) 1.0235(4) 0.0608(8) Uani d 1 . .
    H H3 0.840170 0.407744 1.107439 0.073 Uiso calc 1 . .
    C C4 0.8964(5) 0.5900(4) 1.0695(5) 0.0692(9) Uani d 1 . .
    H H4 0.950320 0.612645 1.186509 0.083 Uiso calc 1 . .
    C C5 0.8830(5) 0.6805(4) 0.9467(5) 0.0709(9) Uani d 1 . .
    H H5 0.926088 0.763121 0.981803 0.085 Uiso calc 1 . .
    C C6 0.8069(4) 0.6495(3) 0.7743(5) 0.0660(9) Uani d 1 . .
    H H6 0.797958 0.710952 0.692294 0.079 Uiso calc 1 . .
    C C7 0.7419(4) 0.5244(3) 0.7208(4) 0.0539(7) Uani d 1 . .
    C C8 0.6589(4) 0.4598(4) 0.5573(4) 0.0619(8) Uani d 1 . .
    C C9 0.6235(5) 0.5204(5) 0.3860(4) 0.0855(13) Uani d 1 . .
    H H9A 0.642061 0.612333 0.403785 0.103 Uiso calc 1 . .
    H H9B 0.709578 0.488038 0.351364 0.103 Uiso calc 1 . .
    C C10 0.4504(5) 0.4997(4) 0.2431(4) 0.0721(11) Uani d 1 . .
    H H10A 0.361947 0.519546 0.280822 0.086 Uiso calc 1 . .
    H H10B 0.437557 0.410028 0.208452 0.086 Uiso calc 1 . .
    C C11 0.2920(4) 0.5382(3) -0.0766(3) 0.0492(6) Uani d 1 . .
    H H11 0.177680 0.540657 -0.075896 0.059 Uiso calc 1 . .
    C C12 0.3181(4) 0.4030(3) -0.1291(4) 0.0596(8) Uani d 1 . .
    H H12A 0.431796 0.397430 -0.128156 0.072 Uiso calc 1 . .
    H H12B 0.315875 0.341579 -0.045337 0.072 Uiso calc 1 . .
    C C13 0.1762(6) 0.3695(4) -0.3085(5) 0.0757(10) Uani d 1 . .
    H H13A 0.196778 0.283691 -0.339441 0.091 Uiso calc 1 . .
    H H13B 0.063234 0.369608 -0.307234 0.091 Uiso calc 1 . .
    C C14 0.1723(5) 0.4639(5) -0.4431(5) 0.0786(11) Uani d 1 . .
    H H14A 0.281049 0.458099 -0.452537 0.094 Uiso calc 1 . .
    H H14B 0.076703 0.442457 -0.555435 0.094 Uiso calc 1 . .
    C C15 0.1490(5) 0.5982(4) -0.3946(4) 0.0705(9) Uani d 1 . .
    H H15A 0.033473 0.606436 -0.400188 0.085 Uiso calc 1 . .
    H H15B 0.155915 0.657786 -0.477959 0.085 Uiso calc 1 . .
    C C16 0.2870(5) 0.6337(3) -0.2129(4) 0.0657(9) Uani d 1 . .
    H H16A 0.262024 0.718893 -0.183813 0.079 Uiso calc 1 . .
    H H16B 0.401106 0.636367 -0.211442 0.079 Uiso calc 1 . .
    H H2 0.524(3) 0.594(5) 0.083(5) 0.091(14) Uiso d 1 . .
    H H1 0.672(5) 0.249(2) 0.813(4) 0.067(11) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C1 . 1.383(4) ?
    N1 C2 . 1.372(4) ?
    N1 H1 . 0.864(14) ?
    N2 C10 . 1.467(4) ?
    N2 C11 . 1.464(4) ?
    N2 H2 . 0.912(14) ?
    C1 H1A . 0.9300 ?
    C1 C8 . 1.357(5) ?
    C2 C3 . 1.388(4) ?
    C2 C7 . 1.410(4) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.375(5) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.382(5) ?
    C5 H5 . 0.9300 ?
    C5 C6 . 1.364(5) ?
    C6 H6 . 0.9300 ?
    C6 C7 . 1.408(5) ?
    C7 C8 . 1.428(5) ?
    C8 C9 . 1.505(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C9 C10 . 1.452(5) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11 . 0.9800 ?
    C11 C12 . 1.523(4) ?
    C11 C16 . 1.524(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 C13 . 1.514(5) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C13 C14 . 1.508(6) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 C15 . 1.497(6) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 C16 . 1.521(5) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
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 H1 . . 124(3) ?
    C2 N1 C1 . . 107.2(3) ?
    C2 N1 H1 . . 129(2) ?
    C10 N2 H2 . . 113(3) ?
    C11 N2 C10 . . 116.6(3) ?
    C11 N2 H2 . . 106(2) ?
    N1 C1 H1A . . 124.5 ?
    C8 C1 N1 . . 111.1(3) ?
    C8 C1 H1A . . 124.5 ?
    N1 C2 C3 . . 130.3(3) ?
    N1 C2 C7 . . 108.6(3) ?
    C3 C2 C7 . . 121.1(3) ?
    C2 C3 H3 . . 120.9 ?
    C4 C3 C2 . . 118.3(3) ?
    C4 C3 H3 . . 120.9 ?
    C3 C4 H4 . . 119.1 ?
    C3 C4 C5 . . 121.8(4) ?
    C5 C4 H4 . . 119.1 ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 C4 . . 120.5(4) ?
    C6 C5 H5 . . 119.8 ?
    C5 C6 H6 . . 120.0 ?
    C5 C6 C7 . . 119.9(3) ?
    C7 C6 H6 . . 120.0 ?
    C2 C7 C8 . . 106.7(3) ?
    C6 C7 C2 . . 118.4(3) ?
    C6 C7 C8 . . 134.9(3) ?
    C1 C8 C7 . . 106.4(3) ?
    C1 C8 C9 . . 129.4(4) ?
    C7 C8 C9 . . 124.1(4) ?
    C8 C9 H9A . . 108.2 ?
    C8 C9 H9B . . 108.2 ?
    H9A C9 H9B . . 107.3 ?
    C10 C9 C8 . . 116.5(3) ?
    C10 C9 H9A . . 108.2 ?
    C10 C9 H9B . . 108.2 ?
    N2 C10 H10A . . 109.5 ?
    N2 C10 H10B . . 109.5 ?
    C9 C10 N2 . . 110.6(3) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    N2 C11 H11 . . 107.8 ?
    N2 C11 C12 . . 115.5(3) ?
    N2 C11 C16 . . 108.5(2) ?
    C12 C11 H11 . . 107.8 ?
    C12 C11 C16 . . 109.3(2) ?
    C16 C11 H11 . . 107.8 ?
    C11 C12 H12A . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    H12A C12 H12B . . 108.0 ?
    C13 C12 C11 . . 111.0(3) ?
    C13 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C12 C13 H13A . . 109.3 ?
    C12 C13 H13B . . 109.3 ?
    H13A C13 H13B . . 108.0 ?
    C14 C13 C12 . . 111.4(3) ?
    C14 C13 H13A . . 109.3 ?
    C14 C13 H13B . . 109.3 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 108.1 ?
    C15 C14 C13 . . 110.6(3) ?
    C15 C14 H14A . . 109.5 ?
    C15 C14 H14B . . 109.5 ?
    C14 C15 H15A . . 109.2 ?
    C14 C15 H15B . . 109.2 ?
    C14 C15 C16 . . 112.0(3) ?
    H15A C15 H15B . . 107.9 ?
    C16 C15 H15A . . 109.2 ?
    C16 C15 H15B . . 109.2 ?
    C11 C16 H16A . . 109.2 ?
    C11 C16 H16B . . 109.2 ?
    C15 C16 C11 . . 112.0(3) ?
    C15 C16 H16A . . 109.2 ?
    C15 C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
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
    N1 C1 C8 C7 . . . . -0.6(4) ?
    N1 C1 C8 C9 . . . . 178.0(3) ?
    N1 C2 C3 C4 . . . . 178.7(3) ?
    N1 C2 C7 C6 . . . . 179.9(3) ?
    N1 C2 C7 C8 . . . . 0.2(3) ?
    N2 C11 C12 C13 . . . . -179.1(3) ?
    N2 C11 C16 C15 . . . . -178.4(3) ?
    C1 N1 C2 C3 . . . . -179.5(3) ?
    C1 N1 C2 C7 . . . . -0.5(3) ?
    C1 C8 C9 C10 . . . . 47.2(6) ?
    C2 N1 C1 C8 . . . . 0.7(4) ?
    C2 C3 C4 C5 . . . . 1.2(5) ?
    C2 C7 C8 C1 . . . . 0.2(3) ?
    C2 C7 C8 C9 . . . . -178.4(3) ?
    C3 C2 C7 C6 . . . . -1.0(4) ?
    C3 C2 C7 C8 . . . . 179.3(3) ?
    C3 C4 C5 C6 . . . . -1.0(5) ?
    C4 C5 C6 C7 . . . . -0.2(5) ?
    C5 C6 C7 C2 . . . . 1.1(4) ?
    C5 C6 C7 C8 . . . . -179.2(3) ?
    C6 C7 C8 C1 . . . . -179.4(3) ?
    C6 C7 C8 C9 . . . . 1.9(5) ?
    C7 C2 C3 C4 . . . . -0.2(4) ?
    C7 C8 C9 C10 . . . . -134.5(4) ?
    C8 C9 C10 N2 . . . . 170.4(4) ?
    C10 N2 C11 C12 . . . . -56.0(4) ?
    C10 N2 C11 C16 . . . . -179.0(3) ?
    C11 N2 C10 C9 . . . . 156.9(4) ?
    C11 C12 C13 C14 . . . . 58.1(4) ?
    C12 C11 C16 C15 . . . . 54.9(4) ?
    C12 C13 C14 C15 . . . . -56.4(4) ?
    C13 C14 C15 C16 . . . . 54.5(4) ?
    C14 C15 C16 C11 . . . . -54.9(4) ?
    C16 C11 C12 C13 . . . . -56.5(4) ?
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 N2 2_646 0.864(14) 2.222(16) 3.069(4) 167(3) yes
_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     0.976
_shelx_estimated_absorpt_T_max     0.986
data_II
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_systematic
;
N-[2-(1H-Indol-3-yl)ethyl]cyclohexanaminium bromide
;
_chemical_name_common
;
N-Cyclohexyltryptammonium bromide
;
_chemical_formula_moiety     'C16 H23 N2 +, Br -'
_chemical_formula_sum     'C16 H23 Br N2'
_chemical_formula_iupac     'C16 H23 N2 +, Br -'
_chemical_formula_weight     323.27
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.5584(6)
_cell_length_b     7.9266(5)
_cell_length_c     19.4507(13)
_cell_angle_alpha     90
_cell_angle_beta     92.406(2)
_cell_angle_gamma     90
_cell_volume     1626.44(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9846
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     26.29
_cell_measurement_temperature     297(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.320
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     2.518
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.6095
_exptl_absorpt_correction_T_max     0.7454
_diffrn_ambient_temperature     297.15
_diffrn_source     ?
_diffrn_source_power     1.5
_diffrn_source_voltage     50.0
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Venture CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     46579
_diffrn_reflns_av_R_equivalents     0.0373
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_theta_min     3.215
_diffrn_reflns_theta_max     26.404
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     3320
_reflns_number_gt     2978
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0493
_refine_ls_R_factor_gt     0.0445
_refine_ls_wR_factor_gt     0.1070
_refine_ls_wR_factor_ref     0.1087
_refine_ls_goodness_of_fit_ref     1.224
_refine_ls_restrained_S_all     1.224
_refine_ls_number_reflns     3320
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                           'w=1/[σ²(Fo²)+4.8013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.582
_refine_diff_density_min     -0.702
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    Br Br1 0.81840(4) 0.64728(5) 0.83341(2) 0.04595(14) Uani d 1 . .
    N N1 0.1405(3) 0.7180(5) 0.8197(2) 0.0510(9) Uani d 1 . .
    N N2 0.6414(3) 0.7350(4) 0.69368(18) 0.0362(7) Uani d 1 . .
    C C1 0.2277(4) 0.7985(6) 0.7822(2) 0.0514(11) Uani d 1 . .
    H H1A 0.208468 0.877881 0.748124 0.062 Uiso calc 1 . .
    C C2 0.2018(4) 0.6091(5) 0.8650(2) 0.0397(9) Uani d 1 . .
    C C3 0.1549(5) 0.5037(6) 0.9141(2) 0.0542(12) Uani d 1 . .
    H H3 0.068295 0.495965 0.920528 0.065 Uiso calc 1 . .
    C C4 0.2401(6) 0.4109(7) 0.9529(3) 0.0680(15) Uani d 1 . .
    H H4 0.211162 0.339725 0.986910 0.082 Uiso calc 1 . .
    C C5 0.3704(6) 0.4212(7) 0.9425(3) 0.0709(15) Uani d 1 . .
    H H5 0.425959 0.354368 0.968979 0.085 Uiso calc 1 . .
    C C6 0.4180(5) 0.5268(6) 0.8944(2) 0.0544(11) Uani d 1 . .
    H H6 0.504805 0.534207 0.888792 0.065 Uiso calc 1 . .
    C C7 0.3330(4) 0.6233(5) 0.85403(19) 0.0364(8) Uani d 1 . .
    C C8 0.3467(4) 0.7472(5) 0.8011(2) 0.0391(9) Uani d 1 . .
    C C9 0.4690(4) 0.8051(6) 0.7726(2) 0.0461(10) Uani d 1 . .
    H H9A 0.533883 0.809465 0.809400 0.055 Uiso calc 1 . .
    H H9B 0.458286 0.918033 0.754113 0.055 Uiso calc 1 . .
    C C10 0.5116(4) 0.6891(6) 0.7169(2) 0.0443(10) Uani d 1 . .
    H H10A 0.451375 0.694700 0.677896 0.053 Uiso calc 1 . .
    H H10B 0.512820 0.574023 0.733848 0.053 Uiso calc 1 . .
    C C11 0.6844(4) 0.6344(5) 0.6336(2) 0.0398(9) Uani d 1 . .
    H H11 0.666538 0.515102 0.642099 0.048 Uiso calc 1 . .
    C C12 0.6154(4) 0.6853(6) 0.5674(2) 0.0481(11) Uani d 1 . .
    H H12A 0.630562 0.803842 0.558442 0.058 Uiso calc 1 . .
    H H12B 0.524985 0.669392 0.571593 0.058 Uiso calc 1 . .
    C C13 0.6611(5) 0.5796(7) 0.5079(3) 0.0591(13) Uani d 1 . .
    H H13A 0.639096 0.462249 0.515003 0.071 Uiso calc 1 . .
    H H13B 0.618863 0.616791 0.465273 0.071 Uiso calc 1 . .
    C C14 0.8031(5) 0.5951(7) 0.5020(2) 0.0616(14) Uani d 1 . .
    H H14A 0.830564 0.521421 0.465755 0.074 Uiso calc 1 . .
    H H14B 0.824146 0.710124 0.489862 0.074 Uiso calc 1 . .
    C C15 0.8720(5) 0.5486(8) 0.5691(3) 0.0676(15) Uani d 1 . .
    H H15A 0.962363 0.565437 0.564858 0.081 Uiso calc 1 . .
    H H15B 0.857931 0.430226 0.578863 0.081 Uiso calc 1 . .
    C C16 0.8262(4) 0.6553(7) 0.6284(2) 0.0559(12) Uani d 1 . .
    H H16A 0.868998 0.620155 0.671109 0.067 Uiso calc 1 . .
    H H16B 0.846249 0.772986 0.620616 0.067 Uiso calc 1 . .
    H H2A 0.692(3) 0.722(6) 0.7316(13) 0.045(12) Uiso d 1 . .
    H H1 0.0593(14) 0.738(6) 0.815(2) 0.058(14) Uiso d 1 . .
    H H2B 0.636(4) 0.844(2) 0.681(2) 0.045(12) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C1 . 1.358(6) ?
    N1 C2 . 1.375(5) ?
    N1 H1 . 0.873(10) ?
    N2 C10 . 1.506(5) ?
    N2 C11 . 1.501(5) ?
    N2 H2A . 0.898(10) ?
    N2 H2B . 0.900(10) ?
    C1 H1A . 0.9300 ?
    C1 C8 . 1.357(6) ?
    C2 C3 . 1.376(6) ?
    C2 C7 . 1.415(5) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.366(7) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.402(8) ?
    C5 H5 . 0.9300 ?
    C5 C6 . 1.366(7) ?
    C6 H6 . 0.9300 ?
    C6 C7 . 1.396(6) ?
    C7 C8 . 1.434(6) ?
    C8 C9 . 1.499(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C9 C10 . 1.504(6) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11 . 0.9800 ?
    C11 C12 . 1.506(6) ?
    C11 C16 . 1.515(6) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 C13 . 1.525(6) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C13 C14 . 1.513(7) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 C15 . 1.513(7) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 C16 . 1.525(7) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
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 . . 109.2(4) ?
    C1 N1 H1 . . 123(3) ?
    C2 N1 H1 . . 128(3) ?
    C10 N2 H2A . . 104(3) ?
    C10 N2 H2B . . 105(3) ?
    C11 N2 C10 . . 114.5(3) ?
    C11 N2 H2A . . 113(3) ?
    C11 N2 H2B . . 109(3) ?
    H2A N2 H2B . . 111(4) ?
    N1 C1 H1A . . 124.6 ?
    C8 C1 N1 . . 110.7(4) ?
    C8 C1 H1A . . 124.6 ?
    N1 C2 C3 . . 130.7(4) ?
    N1 C2 C7 . . 106.9(3) ?
    C3 C2 C7 . . 122.4(4) ?
    C2 C3 H3 . . 121.2 ?
    C4 C3 C2 . . 117.6(5) ?
    C4 C3 H3 . . 121.2 ?
    C3 C4 H4 . . 119.5 ?
    C3 C4 C5 . . 121.1(5) ?
    C5 C4 H4 . . 119.5 ?
    C4 C5 H5 . . 119.1 ?
    C6 C5 C4 . . 121.8(5) ?
    C6 C5 H5 . . 119.1 ?
    C5 C6 H6 . . 120.8 ?
    C5 C6 C7 . . 118.4(5) ?
    C7 C6 H6 . . 120.8 ?
    C2 C7 C8 . . 106.9(3) ?
    C6 C7 C2 . . 118.8(4) ?
    C6 C7 C8 . . 134.2(4) ?
    C1 C8 C7 . . 106.3(4) ?
    C1 C8 C9 . . 127.6(4) ?
    C7 C8 C9 . . 126.1(4) ?
    C8 C9 H9A . . 109.3 ?
    C8 C9 H9B . . 109.3 ?
    C8 C9 C10 . . 111.6(3) ?
    H9A C9 H9B . . 108.0 ?
    C10 C9 H9A . . 109.3 ?
    C10 C9 H9B . . 109.3 ?
    N2 C10 H10A . . 109.3 ?
    N2 C10 H10B . . 109.3 ?
    C9 C10 N2 . . 111.8(3) ?
    C9 C10 H10A . . 109.3 ?
    C9 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 107.9 ?
    N2 C11 H11 . . 108.3 ?
    N2 C11 C12 . . 111.9(3) ?
    N2 C11 C16 . . 109.0(4) ?
    C12 C11 H11 . . 108.3 ?
    C12 C11 C16 . . 111.0(3) ?
    C16 C11 H11 . . 108.3 ?
    C11 C12 H12A . . 109.6 ?
    C11 C12 H12B . . 109.6 ?
    C11 C12 C13 . . 110.2(4) ?
    H12A C12 H12B . . 108.1 ?
    C13 C12 H12A . . 109.6 ?
    C13 C12 H12B . . 109.6 ?
    C12 C13 H13A . . 109.4 ?
    C12 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
    C14 C13 C12 . . 111.0(4) ?
    C14 C13 H13A . . 109.4 ?
    C14 C13 H13B . . 109.4 ?
    C13 C14 H14A . . 109.4 ?
    C13 C14 H14B . . 109.4 ?
    H14A C14 H14B . . 108.0 ?
    C15 C14 C13 . . 111.0(4) ?
    C15 C14 H14A . . 109.4 ?
    C15 C14 H14B . . 109.4 ?
    C14 C15 H15A . . 109.4 ?
    C14 C15 H15B . . 109.4 ?
    C14 C15 C16 . . 111.1(4) ?
    H15A C15 H15B . . 108.0 ?
    C16 C15 H15A . . 109.4 ?
    C16 C15 H15B . . 109.4 ?
    C11 C16 C15 . . 109.6(4) ?
    C11 C16 H16A . . 109.7 ?
    C11 C16 H16B . . 109.7 ?
    C15 C16 H16A . . 109.7 ?
    C15 C16 H16B . . 109.7 ?
    H16A C16 H16B . . 108.2 ?
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
    N1 C1 C8 C7 . . . . 0.8(5) ?
    N1 C1 C8 C9 . . . . -179.9(4) ?
    N1 C2 C3 C4 . . . . -178.8(5) ?
    N1 C2 C7 C6 . . . . 179.1(4) ?
    N1 C2 C7 C8 . . . . 0.9(4) ?
    N2 C11 C12 C13 . . . . -179.6(4) ?
    N2 C11 C16 C15 . . . . 177.9(4) ?
    C1 N1 C2 C3 . . . . 178.5(5) ?
    C1 N1 C2 C7 . . . . -0.4(5) ?
    C1 C8 C9 C10 . . . . -95.0(6) ?
    C2 N1 C1 C8 . . . . -0.3(6) ?
    C2 C3 C4 C5 . . . . -0.8(8) ?
    C2 C7 C8 C1 . . . . -1.0(5) ?
    C2 C7 C8 C9 . . . . 179.6(4) ?
    C3 C2 C7 C6 . . . . 0.1(6) ?
    C3 C2 C7 C8 . . . . -178.2(4) ?
    C3 C4 C5 C6 . . . . 1.6(9) ?
    C4 C5 C6 C7 . . . . -1.5(8) ?
    C5 C6 C7 C2 . . . . 0.6(7) ?
    C5 C6 C7 C8 . . . . 178.3(5) ?
    C6 C7 C8 C1 . . . . -178.9(5) ?
    C6 C7 C8 C9 . . . . 1.8(8) ?
    C7 C2 C3 C4 . . . . 0.0(7) ?
    C7 C8 C9 C10 . . . . 84.2(5) ?
    C8 C9 C10 N2 . . . . -173.5(4) ?
    C10 N2 C11 C12 . . . . 73.0(4) ?
    C10 N2 C11 C16 . . . . -163.9(4) ?
    C11 N2 C10 C9 . . . . -174.5(3) ?
    C11 C12 C13 C14 . . . . -56.6(5) ?
    C12 C11 C16 C15 . . . . -58.5(5) ?
    C12 C13 C14 C15 . . . . 55.5(6) ?
    C13 C14 C15 C16 . . . . -56.0(6) ?
    C14 C15 C16 C11 . . . . 57.0(6) ?
    C16 C11 C12 C13 . . . . 58.4(5) ?
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 Br1 . 0.898(10) 2.414(12) 3.307(4) 172(4) yes
    N1 H1 Br1 1_455 0.873(10) 2.68(3) 3.468(4) 151(4) yes
    N2 H2B Br1 2_656 0.900(10) 2.470(16) 3.340(3) 163(4) yes
_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     0.519
_shelx_estimated_absorpt_T_max     0.928
data_III
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_systematic
;
Bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium}
(2E)-but-2-enedioate
;
_chemical_name_common
;
N-Cyclohexyltryptammonium fumarate
;
_chemical_formula_moiety     'C16 H23 N2 +, C2 H O2 -'
_chemical_formula_sum     'C18 H24 N2 O2'
_chemical_formula_iupac     'C16 H23 N2 +, C2 H O2 -'
_chemical_formula_weight     300.39
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.2231(10)
_cell_length_b     16.1611(16)
_cell_length_c     11.4595(12)
_cell_angle_alpha     90
_cell_angle_beta     99.865(4)
_cell_angle_gamma     90
_cell_volume     1682.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7849
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     26.33
_cell_measurement_temperature     297(2)
_exptl_crystal_description     block
_exptl_crystal_colour     bronze
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.186
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     648
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.6941
_exptl_absorpt_correction_T_max     0.7454
_diffrn_ambient_temperature     297.15
_diffrn_source     ?
_diffrn_source_power     1.5
_diffrn_source_voltage     50.0
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Venture CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20060
_diffrn_reflns_av_R_equivalents     0.0276
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_theta_min     2.571
_diffrn_reflns_theta_max     26.404
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     3446
_reflns_number_gt     2803
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0546
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1112
_refine_ls_wR_factor_ref     0.1214
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     3446
_refine_ls_number_parameters     211
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0570P)²+0.4152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.221
_refine_diff_density_min     -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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 O2 0.72753(11) 0.47420(7) 0.97368(12) 0.0632(3) Uani d 1 . .
    O O4 0.74997(12) 0.60453(6) 1.03308(11) 0.0600(3) Uani d 1 . .
    N N1 0.33759(16) 0.73002(8) 0.54717(12) 0.0530(3) Uani d 1 . .
    N N2 0.46996(12) 0.42877(7) 0.83748(10) 0.0402(3) Uani d 1 . .
    C C1 0.43744(18) 0.68408(10) 0.62215(13) 0.0522(4) Uani d 1 . .
    H H1A 0.513836 0.706133 0.676833 0.063 Uiso calc 1 . .
    C C2 0.24236(16) 0.67738(9) 0.48012(12) 0.0444(3) Uani d 1 . .
    C C3 0.12270(18) 0.69461(11) 0.39157(14) 0.0589(4) Uani d 1 . .
    H H3 0.095302 0.748764 0.371017 0.071 Uiso calc 1 . .
    C C4 0.0471(2) 0.62879(15) 0.33603(17) 0.0753(5) Uani d 1 . .
    H H4 -0.032377 0.638517 0.275820 0.090 Uiso calc 1 . .
    C C5 0.0863(2) 0.54759(14) 0.36747(19) 0.0780(6) Uani d 1 . .
    H H5 0.032566 0.504233 0.327913 0.094 Uiso calc 1 . .
    C C6 0.20302(19) 0.53036(10) 0.45603(16) 0.0609(4) Uani d 1 . .
    H H6 0.227496 0.475901 0.477033 0.073 Uiso calc 1 . .
    C C7 0.28409(15) 0.59569(8) 0.51382(12) 0.0426(3) Uani d 1 . .
    C C8 0.41022(16) 0.60185(9) 0.60614(12) 0.0452(3) Uani d 1 . .
    C C9 0.48890(17) 0.53145(10) 0.67518(14) 0.0523(4) Uani d 1 . .
    H H9A 0.584225 0.550063 0.715932 0.063 Uiso calc 1 . .
    H H9B 0.504732 0.487268 0.621464 0.063 Uiso calc 1 . .
    C C10 0.39908(16) 0.49921(9) 0.76478(13) 0.0475(3) Uani d 1 . .
    H H10A 0.382929 0.544073 0.817299 0.057 Uiso calc 1 . .
    H H10B 0.303662 0.481452 0.723096 0.057 Uiso calc 1 . .
    C C11 0.50069(15) 0.35126(8) 0.77365(12) 0.0423(3) Uani d 1 . .
    H H11 0.565930 0.364743 0.717251 0.051 Uiso calc 1 . .
    C C12 0.57867(19) 0.29119(10) 0.86470(15) 0.0577(4) Uani d 1 . .
    H H12A 0.519809 0.282701 0.926173 0.069 Uiso calc 1 . .
    H H12B 0.672434 0.314467 0.901290 0.069 Uiso calc 1 . .
    C C13 0.6045(2) 0.20810(11) 0.80791(19) 0.0785(6) Uani d 1 . .
    H H13A 0.671411 0.215725 0.752071 0.094 Uiso calc 1 . .
    H H13B 0.649859 0.169933 0.868687 0.094 Uiso calc 1 . .
    C C14 0.4613(3) 0.17171(11) 0.74422(18) 0.0784(6) Uani d 1 . .
    H H14A 0.480951 0.120240 0.706292 0.094 Uiso calc 1 . .
    H H14B 0.397404 0.159654 0.801073 0.094 Uiso calc 1 . .
    C C15 0.3856(3) 0.23094(13) 0.65269(16) 0.0783(6) Uani d 1 . .
    H H15A 0.291923 0.207658 0.615817 0.094 Uiso calc 1 . .
    H H15B 0.445353 0.238438 0.591619 0.094 Uiso calc 1 . .
    C C16 0.35933(18) 0.31489(11) 0.70660(14) 0.0584(4) Uani d 1 . .
    H H16A 0.317379 0.352639 0.644040 0.070 Uiso calc 1 . .
    H H16B 0.289125 0.308535 0.760051 0.070 Uiso calc 1 . .
    C C17 0.80163(14) 0.53717(8) 1.00368(12) 0.0397(3) Uani d 1 . .
    C C18 0.96469(14) 0.53303(8) 1.01170(12) 0.0401(3) Uani d 1 . .
    H H18 1.019151 0.580476 1.034817 0.048 Uiso calc 1 . .
    H H2A 0.5558(13) 0.4470(10) 0.8805(13) 0.061(5) Uiso d 1 . .
    H H1 0.330(2) 0.7840(6) 0.5455(17) 0.075(6) Uiso d 1 . .
    H H2B 0.4089(16) 0.4143(10) 0.8881(12) 0.057(5) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O2 C17 . 1.2411(16) ?
    O4 C17 . 1.2572(16) ?
    N1 C1 . 1.366(2) ?
    N1 C2 . 1.362(2) ?
    N1 H1 . 0.876(9) ?
    N2 C10 . 1.4935(17) ?
    N2 C11 . 1.5018(18) ?
    N2 H2A . 0.907(9) ?
    N2 H2B . 0.905(9) ?
    C1 H1A . 0.9300 ?
    C1 C8 . 1.359(2) ?
    C2 C3 . 1.393(2) ?
    C2 C7 . 1.4105(19) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.368(3) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.392(3) ?
    C5 H5 . 0.9300 ?
    C5 C6 . 1.376(3) ?
    C6 H6 . 0.9300 ?
    C6 C7 . 1.394(2) ?
    C7 C8 . 1.436(2) ?
    C8 C9 . 1.5000(19) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C9 C10 . 1.518(2) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11 . 0.9800 ?
    C11 C12 . 1.514(2) ?
    C11 C16 . 1.514(2) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 C13 . 1.529(2) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C13 C14 . 1.514(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 C15 . 1.501(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 C16 . 1.527(2) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C18 . 1.4924(18) ?
    C18 C18 3_767 1.302(3) ?
    C18 H18 . 0.9300 ?
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 H1 . . 126.9(13) ?
    C2 N1 C1 . . 108.39(12) ?
    C2 N1 H1 . . 124.6(13) ?
    C10 N2 C11 . . 117.72(11) ?
    C10 N2 H2A . . 108.3(11) ?
    C10 N2 H2B . . 107.1(11) ?
    C11 N2 H2A . . 108.4(11) ?
    C11 N2 H2B . . 106.6(11) ?
    H2A N2 H2B . . 108.5(15) ?
    N1 C1 H1A . . 124.5 ?
    C8 C1 N1 . . 110.95(14) ?
    C8 C1 H1A . . 124.5 ?
    N1 C2 C3 . . 129.78(14) ?
    N1 C2 C7 . . 108.12(12) ?
    C3 C2 C7 . . 122.10(15) ?
    C2 C3 H3 . . 121.3 ?
    C4 C3 C2 . . 117.42(16) ?
    C4 C3 H3 . . 121.3 ?
    C3 C4 H4 . . 119.2 ?
    C3 C4 C5 . . 121.59(16) ?
    C5 C4 H4 . . 119.2 ?
    C4 C5 H5 . . 119.4 ?
    C6 C5 C4 . . 121.16(18) ?
    C6 C5 H5 . . 119.4 ?
    C5 C6 H6 . . 120.5 ?
    C5 C6 C7 . . 119.05(16) ?
    C7 C6 H6 . . 120.5 ?
    C2 C7 C8 . . 106.59(12) ?
    C6 C7 C2 . . 118.68(14) ?
    C6 C7 C8 . . 134.73(14) ?
    C1 C8 C7 . . 105.96(12) ?
    C1 C8 C9 . . 127.52(14) ?
    C7 C8 C9 . . 126.43(13) ?
    C8 C9 H9A . . 109.6 ?
    C8 C9 H9B . . 109.6 ?
    C8 C9 C10 . . 110.27(12) ?
    H9A C9 H9B . . 108.1 ?
    C10 C9 H9A . . 109.6 ?
    C10 C9 H9B . . 109.6 ?
    N2 C10 C9 . . 113.68(11) ?
    N2 C10 H10A . . 108.8 ?
    N2 C10 H10B . . 108.8 ?
    C9 C10 H10A . . 108.8 ?
    C9 C10 H10B . . 108.8 ?
    H10A C10 H10B . . 107.7 ?
    N2 C11 H11 . . 108.9 ?
    N2 C11 C12 . . 107.83(12) ?
    N2 C11 C16 . . 110.67(11) ?
    C12 C11 H11 . . 108.9 ?
    C12 C11 C16 . . 111.52(13) ?
    C16 C11 H11 . . 108.9 ?
    C11 C12 H12A . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    C11 C12 C13 . . 111.11(14) ?
    H12A C12 H12B . . 108.0 ?
    C13 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C12 C13 H13A . . 109.4 ?
    C12 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
    C14 C13 C12 . . 111.08(16) ?
    C14 C13 H13A . . 109.4 ?
    C14 C13 H13B . . 109.4 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 108.1 ?
    C15 C14 C13 . . 110.62(16) ?
    C15 C14 H14A . . 109.5 ?
    C15 C14 H14B . . 109.5 ?
    C14 C15 H15A . . 109.3 ?
    C14 C15 H15B . . 109.3 ?
    C14 C15 C16 . . 111.77(14) ?
    H15A C15 H15B . . 107.9 ?
    C16 C15 H15A . . 109.3 ?
    C16 C15 H15B . . 109.3 ?
    C11 C16 C15 . . 111.59(15) ?
    C11 C16 H16A . . 109.3 ?
    C11 C16 H16B . . 109.3 ?
    C15 C16 H16A . . 109.3 ?
    C15 C16 H16B . . 109.3 ?
    H16A C16 H16B . . 108.0 ?
    O2 C17 O4 . . 124.62(13) ?
    O2 C17 C18 . . 118.79(12) ?
    O4 C17 C18 . . 116.52(12) ?
    C17 C18 H18 . . 118.0 ?
    C18 C18 C17 3_767 . 123.95(16) ?
    C18 C18 H18 3_767 . 118.0 ?
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 C17 C18 C18 . . . 3_767 0.5(3) ?
    O4 C17 C18 C18 . . . 3_767 177.60(18) ?
    N1 C1 C8 C7 . . . . 0.23(17) ?
    N1 C1 C8 C9 . . . . -176.30(14) ?
    N1 C2 C3 C4 . . . . 178.46(16) ?
    N1 C2 C7 C6 . . . . -179.33(14) ?
    N1 C2 C7 C8 . . . . 0.35(16) ?
    N2 C11 C12 C13 . . . . 176.04(14) ?
    N2 C11 C16 C15 . . . . -173.47(13) ?
    C1 N1 C2 C3 . . . . -179.77(15) ?
    C1 N1 C2 C7 . . . . -0.21(16) ?
    C1 C8 C9 C10 . . . . 101.09(19) ?
    C2 N1 C1 C8 . . . . -0.02(18) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C2 C7 C8 C1 . . . . -0.35(16) ?
    C2 C7 C8 C9 . . . . 176.23(13) ?
    C3 C2 C7 C6 . . . . 0.3(2) ?
    C3 C2 C7 C8 . . . . 179.95(13) ?
    C3 C4 C5 C6 . . . . 0.0(3) ?
    C4 C5 C6 C7 . . . . -0.8(3) ?
    C5 C6 C7 C2 . . . . 0.7(2) ?
    C5 C6 C7 C8 . . . . -178.90(17) ?
    C6 C7 C8 C1 . . . . 179.25(17) ?
    C6 C7 C8 C9 . . . . -4.2(3) ?
    C7 C2 C3 C4 . . . . -1.0(2) ?
    C7 C8 C9 C10 . . . . -74.77(19) ?
    C8 C9 C10 N2 . . . . 180.00(12) ?
    C10 N2 C11 C12 . . . . 177.27(12) ?
    C10 N2 C11 C16 . . . . -60.50(16) ?
    C11 N2 C10 C9 . . . . -60.41(17) ?
    C11 C12 C13 C14 . . . . -56.1(2) ?
    C12 C11 C16 C15 . . . . -53.43(19) ?
    C12 C13 C14 C15 . . . . 56.9(2) ?
    C13 C14 C15 C16 . . . . -56.1(2) ?
    C14 C15 C16 C11 . . . . 54.6(2) ?
    C16 C11 C12 C13 . . . . 54.34(19) ?
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 O2 . 0.907(9) 1.807(9) 2.7107(15) 174.6(16) yes
    N1 H1 O4 4_575 0.876(9) 1.941(11) 2.7899(16) 162.7(18) yes
    N2 H2B O4 3_667 0.905(9) 1.873(10) 2.7632(16) 167.0(15) yes
_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     0.976
_shelx_estimated_absorpt_T_max     0.985
