##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2019-10-09
_journal_date_accepted     2019-10-29
_journal_name_full     'IUCrData'
_journal_year     2019
_journal_volume     4
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431461901469X
_journal_coeditor_code     FF4032
_publ_contact_author_name     'Andrew R. Chadeayne'
_publ_contact_author_address
;
CaamTech, LLC,
58 East Sunset Way, Suite 209,
Issaquah, WA 98027,
USA
;
_publ_contact_author_email     andrew@caam.tech
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate
tetrahydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chadeayne, Andrew R.' .
;
CaaMTech, LLC,
58 East Sunset Way, Suite 209,
Issaquah, WA 98027,
USA
;
    'Pham, Duyen N. K.' .
;
285 Old Westport Rd.,
North Dartmouth, MA, 02747,
USA
;
    'Golen, James A.' .
;
285 Old Westport Rd.,
North Dartmouth, MA, 02747,
USA
;
    'Manke, David R.' .
;
285 Old Westport Rd.,
North Dartmouth, MA, 02747,
USA
;
_publ_section_synopsis
;
The crystal structure of the fumarate salt of the synthetic psychedelic
4-HO-DPT is reported as its tetrahydrate. A series of N---H...O and O---H...O
hydrogen bonds connect the ions and water molecules of crystallization into a
three-dimensional network.
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1962339,1962339'
_chemical_name_systematic
;
Bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium}
but-2-enedioate tetrahydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H25 N2 O +, 0.5(C4 H2 O4 2-), 2(H2 O)'
_chemical_formula_sum     'C18 H30 N2 O5'
_chemical_formula_iupac     'C16 H25 N2 O +, 0.5C4 H2 O4 2-, 2H2 O'
_chemical_formula_weight     354.44
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_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     8.3495(8)
_cell_length_b     12.5138(11)
_cell_length_c     18.6631(17)
_cell_angle_alpha     90
_cell_angle_beta     100.902(3)
_cell_angle_gamma     90
_cell_volume     1914.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9972
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     25.21
_cell_measurement_temperature     200(2)
_exptl_crystal_description     'shard'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.229
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.7046
_exptl_absorpt_correction_T_max     0.7452
_diffrn_ambient_temperature     200.0
_diffrn_source     ?
_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     52418
_diffrn_reflns_av_R_equivalents     0.0607
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_theta_min     2.907
_diffrn_reflns_theta_max     25.407
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     3512
_reflns_number_gt     2630
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0694
_refine_ls_R_factor_gt     0.0464
_refine_ls_wR_factor_gt     0.1123
_refine_ls_wR_factor_ref     0.1275
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     3512
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0556P)²+0.9970P] 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     0.593
_refine_diff_density_min     -0.216
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick 2018)
;
_refine_ls_extinction_coef     0.0155(18)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     ?
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and 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 O1 0.94852(17) 0.34667(12) 0.25667(7) 0.0394(4) Uani d 1 . .
    O O1W 0.5933(3) 0.38719(15) 0.16468(15) 0.0764(7) Uani d 1 . .
    O O2 1.05696(17) 0.46219(12) 0.15852(7) 0.0445(4) Uani d 1 . .
    O O2W 1.3681(2) 0.53142(15) 0.18964(10) 0.0529(5) Uani d 1 . .
    O O3 0.82210(18) 0.42826(13) 0.08492(7) 0.0457(4) Uani d 1 . .
    N N1 1.0659(3) 0.16741(15) 0.47495(10) 0.0494(5) Uani d 1 . .
    N N2 0.60593(19) 0.17587(13) 0.19118(8) 0.0321(4) Uani d 1 . .
    C C1 0.9055(3) 0.15399(17) 0.44334(11) 0.0468(6) Uani d 1 . .
    H H1B 0.829526 0.112646 0.463512 0.056 Uiso calc 1 . .
    C C2 1.1400(3) 0.23028(15) 0.43090(10) 0.0381(5) Uani d 1 . .
    C C3 1.3016(3) 0.26370(17) 0.43917(12) 0.0459(6) Uani d 1 . .
    H H3 1.380626 0.244438 0.480779 0.055 Uiso calc 1 . .
    C C4 1.3413(3) 0.32549(18) 0.38466(13) 0.0457(5) Uani d 1 . .
    H H4 1.450484 0.349755 0.388895 0.055 Uiso calc 1 . .
    C C5 1.2268(2) 0.35418(16) 0.32296(11) 0.0390(5) Uani d 1 . .
    H H5 1.259699 0.396749 0.286160 0.047 Uiso calc 1 . .
    C C6 1.0666(2) 0.32147(15) 0.31481(10) 0.0312(4) Uani d 1 . .
    C C7 1.0205(2) 0.25791(14) 0.36961(10) 0.0307(4) Uani d 1 . .
    C C8 0.8697(3) 0.20820(15) 0.37881(10) 0.0347(5) Uani d 1 . .
    C C9 0.7111(2) 0.21074(16) 0.32523(11) 0.0372(5) Uani d 1 . .
    H H9A 0.683386 0.285434 0.310371 0.045 Uiso calc 1 . .
    H H9B 0.622912 0.181941 0.348408 0.045 Uiso calc 1 . .
    C C10 0.7250(2) 0.14395(16) 0.25814(10) 0.0346(5) Uani d 1 . .
    H H10A 0.836979 0.150899 0.248342 0.042 Uiso calc 1 . .
    H H10B 0.707217 0.067836 0.268820 0.042 Uiso calc 1 . .
    C C11 0.6625(3) 0.13956(16) 0.12321(11) 0.0379(5) Uani d 1 . .
    H H11A 0.584190 0.165736 0.080225 0.045 Uiso calc 1 . .
    H H11B 0.769365 0.173093 0.122033 0.045 Uiso calc 1 . .
    C C12 0.6794(3) 0.02060(19) 0.11654(13) 0.0560(6) Uani d 1 . .
    H H12A 0.573370 -0.013926 0.117888 0.067 Uiso calc 1 . .
    H H12B 0.760009 -0.006282 0.158518 0.067 Uiso calc 1 . .
    C C13 0.7340(3) -0.0092(2) 0.04618(13) 0.0572(6) Uani d 1 . .
    H H13A 0.736537 -0.087204 0.041736 0.086 Uiso calc 1 . .
    H H13B 0.843254 0.019698 0.046637 0.086 Uiso calc 1 . .
    H H13C 0.657436 0.020577 0.004669 0.086 Uiso calc 1 . .
    C C14 0.4340(2) 0.14425(17) 0.19474(11) 0.0397(5) Uani d 1 . .
    H H14A 0.410134 0.165611 0.242711 0.048 Uiso calc 1 . .
    H H14B 0.424083 0.065534 0.190902 0.048 Uiso calc 1 . .
    C C15 0.3094(3) 0.1947(2) 0.13503(14) 0.0594(7) Uani d 1 . .
    H H15A 0.319125 0.273426 0.138887 0.071 Uiso calc 1 . .
    H H15B 0.333208 0.173394 0.087045 0.071 Uiso calc 1 . .
    C C16 0.1391(3) 0.1631(2) 0.13865(15) 0.0615(7) Uani d 1 . .
    H H16A 0.063310 0.198177 0.099119 0.092 Uiso calc 1 . .
    H H16B 0.114132 0.185071 0.185742 0.092 Uiso calc 1 . .
    H H16C 0.127829 0.085439 0.133480 0.092 Uiso calc 1 . .
    C C17 0.9662(2) 0.45901(15) 0.09626(10) 0.0317(4) Uani d 1 . .
    C C18 1.0407(2) 0.49612(15) 0.03381(10) 0.0338(4) Uani d 1 . .
    H H18 1.152918 0.515150 0.043346 0.041 Uiso calc 1 . .
    H H1 0.991(3) 0.383(2) 0.2241(15) 0.066(8) Uiso d 1 . .
    H H2WA 1.372(4) 0.591(3) 0.1719(19) 0.098(12) Uiso d 1 . .
    H H2 0.604(3) 0.254(2) 0.1887(13) 0.052(6) Uiso d 1 . .
    H H2WB 1.261(4) 0.505(2) 0.1751(15) 0.081(9) Uiso d 1 . .
    H H1A 1.121(3) 0.135(2) 0.5147(15) 0.065(8) Uiso d 1 . .
    H H1WA 0.527(4) 0.435(2) 0.1698(15) 0.072(9) Uiso d 1 . .
    H H1WB 0.670(4) 0.403(2) 0.1439(17) 0.079(10) 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
    O1 C6 . 1.358(2) ?
    O1 H1 . 0.88(3) ?
    O1W H1WA . 0.83(3) ?
    O1W H1WB . 0.83(3) ?
    O2 C17 . 1.262(2) ?
    O2W H2WA . 0.82(4) ?
    O2W H2WB . 0.94(3) ?
    O3 C17 . 1.243(2) ?
    N1 C1 . 1.368(3) ?
    N1 C2 . 1.367(3) ?
    N1 H1A . 0.89(3) ?
    N2 C10 . 1.496(2) ?
    N2 C11 . 1.505(3) ?
    N2 C14 . 1.503(2) ?
    N2 H2 . 0.98(2) ?
    C1 H1B . 0.9500 ?
    C1 C8 . 1.365(3) ?
    C2 C3 . 1.393(3) ?
    C2 C7 . 1.411(3) ?
    C3 H3 . 0.9500 ?
    C3 C4 . 1.368(3) ?
    C4 H4 . 0.9500 ?
    C4 C5 . 1.397(3) ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.380(3) ?
    C6 C7 . 1.406(3) ?
    C7 C8 . 1.443(3) ?
    C8 C9 . 1.501(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C9 C10 . 1.528(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C11 C12 . 1.503(3) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C12 C13 . 1.516(3) ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C14 C15 . 1.511(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C15 C16 . 1.489(3) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.495(3) ?
    C18 C18 3_765 1.319(4) ?
    C18 H18 . 0.9500 ?
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
    C6 O1 H1 . . 109.9(17) ?
    H1WA O1W H1WB . . 118(3) ?
    H2WA O2W H2WB . . 108(3) ?
    C1 N1 H1A . . 127.6(17) ?
    C2 N1 C1 . . 109.18(17) ?
    C2 N1 H1A . . 122.8(17) ?
    C10 N2 C11 . . 111.00(15) ?
    C10 N2 C14 . . 112.47(15) ?
    C10 N2 H2 . . 107.9(13) ?
    C11 N2 H2 . . 105.5(14) ?
    C14 N2 C11 . . 114.36(15) ?
    C14 N2 H2 . . 105.0(13) ?
    N1 C1 H1B . . 124.7 ?
    C8 C1 N1 . . 110.7(2) ?
    C8 C1 H1B . . 124.7 ?
    N1 C2 C3 . . 130.15(19) ?
    N1 C2 C7 . . 107.29(19) ?
    C3 C2 C7 . . 122.55(19) ?
    C2 C3 H3 . . 121.5 ?
    C4 C3 C2 . . 116.94(19) ?
    C4 C3 H3 . . 121.5 ?
    C3 C4 H4 . . 118.9 ?
    C3 C4 C5 . . 122.3(2) ?
    C5 C4 H4 . . 118.9 ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 C4 . . 120.8(2) ?
    C6 C5 H5 . . 119.6 ?
    O1 C6 C5 . . 124.15(18) ?
    O1 C6 C7 . . 117.10(17) ?
    C5 C6 C7 . . 118.74(17) ?
    C2 C7 C8 . . 107.28(17) ?
    C6 C7 C2 . . 118.64(18) ?
    C6 C7 C8 . . 134.07(17) ?
    C1 C8 C7 . . 105.59(18) ?
    C1 C8 C9 . . 128.06(19) ?
    C7 C8 C9 . . 126.23(16) ?
    C8 C9 H9A . . 109.7 ?
    C8 C9 H9B . . 109.7 ?
    C8 C9 C10 . . 109.90(16) ?
    H9A C9 H9B . . 108.2 ?
    C10 C9 H9A . . 109.7 ?
    C10 C9 H9B . . 109.7 ?
    N2 C10 C9 . . 113.40(16) ?
    N2 C10 H10A . . 108.9 ?
    N2 C10 H10B . . 108.9 ?
    C9 C10 H10A . . 108.9 ?
    C9 C10 H10B . . 108.9 ?
    H10A C10 H10B . . 107.7 ?
    N2 C11 H11A . . 108.6 ?
    N2 C11 H11B . . 108.6 ?
    H11A C11 H11B . . 107.6 ?
    C12 C11 N2 . . 114.73(17) ?
    C12 C11 H11A . . 108.6 ?
    C12 C11 H11B . . 108.6 ?
    C11 C12 H12A . . 109.4 ?
    C11 C12 H12B . . 109.4 ?
    C11 C12 C13 . . 111.4(2) ?
    H12A C12 H12B . . 108.0 ?
    C13 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N2 C14 H14A . . 109.0 ?
    N2 C14 H14B . . 109.0 ?
    N2 C14 C15 . . 112.81(17) ?
    H14A C14 H14B . . 107.8 ?
    C15 C14 H14A . . 109.0 ?
    C15 C14 H14B . . 109.0 ?
    C14 C15 H15A . . 109.1 ?
    C14 C15 H15B . . 109.1 ?
    H15A C15 H15B . . 107.8 ?
    C16 C15 C14 . . 112.7(2) ?
    C16 C15 H15A . . 109.1 ?
    C16 C15 H15B . . 109.1 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O2 C17 C18 . . 116.23(17) ?
    O3 C17 O2 . . 124.05(17) ?
    O3 C17 C18 . . 119.71(16) ?
    C17 C18 H18 . . 118.2 ?
    C18 C18 C17 3_765 . 123.6(2) ?
    C18 C18 H18 3_765 . 118.2 ?
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
    O1 C6 C7 C2 . . . . -179.92(16) ?
    O1 C6 C7 C8 . . . . 1.6(3) ?
    O2 C17 C18 C18 . . . 3_765 -175.7(2) ?
    O3 C17 C18 C18 . . . 3_765 3.7(4) ?
    N1 C1 C8 C7 . . . . 0.7(2) ?
    N1 C1 C8 C9 . . . . 176.85(19) ?
    N1 C2 C3 C4 . . . . 178.8(2) ?
    N1 C2 C7 C6 . . . . -178.92(17) ?
    N1 C2 C7 C8 . . . . -0.1(2) ?
    N2 C11 C12 C13 . . . . 179.03(18) ?
    N2 C14 C15 C16 . . . . 179.9(2) ?
    C1 N1 C2 C3 . . . . -178.4(2) ?
    C1 N1 C2 C7 . . . . 0.5(2) ?
    C1 C8 C9 C10 . . . . -105.9(2) ?
    C2 N1 C1 C8 . . . . -0.8(3) ?
    C2 C3 C4 C5 . . . . -0.3(3) ?
    C2 C7 C8 C1 . . . . -0.4(2) ?
    C2 C7 C8 C9 . . . . -176.62(18) ?
    C3 C2 C7 C6 . . . . 0.1(3) ?
    C3 C2 C7 C8 . . . . 178.94(18) ?
    C3 C4 C5 C6 . . . . 0.5(3) ?
    C4 C5 C6 O1 . . . . 179.62(18) ?
    C4 C5 C6 C7 . . . . -0.4(3) ?
    C5 C6 C7 C2 . . . . 0.1(3) ?
    C5 C6 C7 C8 . . . . -178.3(2) ?
    C6 C7 C8 C1 . . . . 178.2(2) ?
    C6 C7 C8 C9 . . . . 2.0(3) ?
    C7 C2 C3 C4 . . . . 0.0(3) ?
    C7 C8 C9 C10 . . . . 69.5(2) ?
    C8 C9 C10 N2 . . . . -156.21(16) ?
    C10 N2 C11 C12 . . . . 61.6(2) ?
    C10 N2 C14 C15 . . . . 168.58(19) ?
    C11 N2 C10 C9 . . . . 158.64(16) ?
    C11 N2 C14 C15 . . . . -63.6(2) ?
    C14 N2 C10 C9 . . . . -71.8(2) ?
    C14 N2 C11 C12 . . . . -66.9(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 H1A O3 4_666 0.89(3) 2.08(3) 2.926(2) 157(2) yes
    N2 H2 O1W . 0.98(2) 1.73(3) 2.689(2) 168(2) yes
    O1 H1 O2 . 0.88(3) 1.74(3) 2.625(2) 174(3) yes
    O1W H1WA O2W 1_455 0.83(3) 1.88(3) 2.710(3) 172(3) yes
    O1W H1WB O3 . 0.83(3) 1.86(3) 2.684(3) 171(3) yes
    O2W H2WB O2 . 0.94(3) 1.76(3) 2.695(2) 173(3) yes
    O2W H2WA Cg 2_755 0.82(4) 2.69(4) 3.488(2) 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     0.982
_shelx_estimated_absorpt_T_max     0.991
