##############################################################################
#                                                                            #
# 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    # 
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data_global
_audit_creation_method     'APEX3 v2017.3-0'
_journal_date_recd_electronic     2018-09-05
_journal_date_accepted     2018-09-10
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      9
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618012762
_journal_coeditor_code     HB4260
_publ_contact_author_name     'Wedad Al Garadi'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta, BP
1014, Faculte des Sciences, Universite Mohammed V,
Rabat,
Morocco
;
_publ_contact_author_email     'awedad17@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
4-Phenyl-2,5,5a,6,7,8,9,9a-hexahydro-1H-1,5-benzodiazepine-2-thione
ethanol monosolvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Al Garadi, Wedad' .
;
Laboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta,
BP 1014, Faculté des Sciences, Université Mohammed V,
Rabat,
Morocco
;
    'Ramli, Youssef' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat
Morocco
;
    'El Ghayati, Lhoussaine' .
;
Laboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta,
BP 1014, Faculté des Sciences, Université Mohammed V,
Rabat,
Morocco
;
    'El Hafi, Mohamed' .
;
Laboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta,
BP 1014, Faculté des Sciences, Université Mohammed V,
Rabat,
Morocco
;
    'Moussaif, Ahmed' .
;
National Center of Energy Sciences and Nuclear Techniques
Rabat
Morocco
;
    'Essassi, El Mokhtar' .
;
Laboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta,
BP 1014, Faculté des Sciences, Université Mohammed V,
Rabat,
Morocco
;
    'Mague, Joel T.' .
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
_publ_section_synopsis
;
In the title compound, the seven-membered ring has a twisted envelope
conformation and the saturated six-membered ring a chair conformation. In the
crystal, N---H...O, N---H...S, O---H...S hydrogen bonds and C---H...π
interactions link both main and solvent molecules into layers lying parallel
to (101).
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1866809'
_audit_creation_method     'SHELXL-2018/1'
_chemical_name_systematic
;
4-Phenyl-2,5,5a,6,7,8,9,9a-hexahydro-1H-1,5-benzodiazepine-2-thione
ethanol monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H18 N2 S, C2 H6 O'
_chemical_formula_sum     'C17 H24 N2 O S'
_chemical_formula_iupac     'C15 H18 N2 S, C2 H6 O'
_chemical_formula_weight     304.44
_chemical_melting_point     ?
_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.
;
_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     12.0255(2)
_cell_length_b     8.9303(2)
_cell_length_c     15.8822(3)
_cell_angle_alpha     90
_cell_angle_beta     95.8130(10)
_cell_angle_gamma     90
_cell_volume     1696.84(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8452
_cell_measurement_theta_min     4.858
_cell_measurement_theta_max     70.144
_cell_measurement_temperature     298(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.215
_exptl_crystal_size_mid     0.126
_exptl_crystal_size_min     0.043
_exptl_crystal_density_diffrn     1.192
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     1.689
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_shelx_estimated_absorpt_T_min     0.713
_shelx_estimated_absorpt_T_max     0.931
_exptl_absorpt_correction_T_min     0.71
_exptl_absorpt_correction_T_max     0.93
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12459
_diffrn_reflns_av_R_equivalents     0.0318
_diffrn_reflns_theta_min     4.857
_diffrn_reflns_theta_max     70.138
_diffrn_reflns_theta_full     70.100
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.93 - 0.98 Å) while those
attached to nitrogen and oxygen were placed in locations derived from a
difference map and their coordinates adjusted to give N---H = 0.91 %A.
and O---H = 0.87 Å. All were included as riding contributions with
isotropic displacement parameters 1.2 - 1.5 times those of the attached
atoms. The lattice ethanol is disordered over two sites with the oxygen
atom in common. The components of the disorder were refined with restraints
that their geometries be comparable.
;
_reflns_number_total     3209
_reflns_number_gt     2613
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0549
_refine_ls_R_factor_gt     0.0439
_refine_ls_wR_factor_gt     0.1126
_refine_ls_wR_factor_ref     0.1251
_refine_ls_goodness_of_fit_ref     1.073
_refine_ls_restrained_S_all     1.081
_refine_ls_number_reflns     3209
_refine_ls_number_parameters     199
_refine_ls_number_restraints     26
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0531P)²+0.7241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.301
_refine_diff_density_min     -0.184
_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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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
    S S1 0.04411(5) 0.33255(6) 0.41909(4) 0.0606(2) Uani d 1 . .
    N N1 0.35246(13) 0.63053(17) 0.34690(10) 0.0464(4) Uani d 1 . .
    H H1A 0.415425 0.668287 0.327593 0.056 Uiso d 1 . .
    N N2 0.16991(13) 0.56183(17) 0.46634(9) 0.0470(4) Uani d 1 . .
    H H2 0.109900 0.578865 0.495602 0.056 Uiso d 1 . .
    C C1 0.26404(17) 0.6658(2) 0.47957(12) 0.0484(5) Uani d 1 . .
    H H1 0.329705 0.611765 0.505524 0.058 Uiso calc 1 . .
    C C2 0.2299(2) 0.7841(3) 0.54160(14) 0.0638(6) Uani d 1 . .
    H H2A 0.157157 0.823675 0.520850 0.077 Uiso calc 1 . .
    H H2B 0.223027 0.736859 0.595837 0.077 Uiso calc 1 . .
    C C3 0.3128(2) 0.9130(3) 0.55427(15) 0.0740(7) Uani d 1 . .
    H H3A 0.286707 0.985167 0.593474 0.089 Uiso calc 1 . .
    H H3B 0.384858 0.875486 0.578180 0.089 Uiso calc 1 . .
    C C4 0.3246(2) 0.9874(3) 0.47095(15) 0.0664(6) Uani d 1 . .
    H H4A 0.376771 1.070253 0.479142 0.080 Uiso calc 1 . .
    H H4B 0.252863 1.026899 0.447656 0.080 Uiso calc 1 . .
    C C5 0.3667(2) 0.8748(2) 0.40967(16) 0.0630(6) Uani d 1 . .
    H H5A 0.441443 0.843268 0.431149 0.076 Uiso calc 1 . .
    H H5B 0.371657 0.923603 0.355604 0.076 Uiso calc 1 . .
    C C6 0.29211(16) 0.7361(2) 0.39586(12) 0.0453(4) Uani d 1 . .
    H H6 0.222356 0.764715 0.362434 0.054 Uiso calc 1 . .
    C C7 0.32591(15) 0.4872(2) 0.33075(11) 0.0402(4) Uani d 1 . .
    C C8 0.23849(16) 0.4073(2) 0.35782(12) 0.0461(4) Uani d 1 . .
    H H8 0.229905 0.311777 0.334793 0.055 Uiso calc 1 . .
    C C9 0.15903(16) 0.4448(2) 0.41463(11) 0.0440(4) Uani d 1 . .
    C C10 0.39812(14) 0.4097(2) 0.27311(11) 0.0417(4) Uani d 1 . .
    C C11 0.43429(17) 0.2639(2) 0.28946(13) 0.0521(5) Uani d 1 . .
    H H11 0.415250 0.214890 0.337637 0.062 Uiso calc 1 . .
    C C12 0.49857(19) 0.1908(3) 0.23445(16) 0.0640(6) Uani d 1 . .
    H H12 0.522541 0.093252 0.245910 0.077 Uiso calc 1 . .
    C C13 0.52694(18) 0.2624(3) 0.16295(15) 0.0636(6) Uani d 1 . .
    H H13 0.569293 0.212846 0.125778 0.076 Uiso calc 1 . .
    C C14 0.49280(18) 0.4067(3) 0.14656(14) 0.0586(5) Uani d 1 . .
    H H14 0.512929 0.455074 0.098518 0.070 Uiso calc 1 . .
    C C15 0.42842(16) 0.4814(2) 0.20098(12) 0.0478(4) Uani d 1 . .
    H H15 0.405520 0.579352 0.189269 0.057 Uiso calc 1 . .
    O O1 0.55130(14) 0.7823(2) 0.28035(11) 0.0695(4) Uani d 1 . .
    H H1B 0.527520 0.804551 0.228297 0.083 Uiso d 1 A .
    C C16 0.6566(3) 0.7119(5) 0.2791(2) 0.0730(10) Uani d 0.880(8) A 1
    H H16A 0.714534 0.786480 0.275471 0.088 Uiso calc 0.880(8) A 1
    H H16B 0.655933 0.645981 0.230550 0.088 Uiso calc 0.880(8) A 1
    C C17 0.6787(3) 0.6240(6) 0.3592(4) 0.1058(17) Uani d 0.880(8) A 1
    H H17A 0.620071 0.552021 0.362783 0.159 Uiso calc 0.880(8) A 1
    H H17B 0.681220 0.690618 0.406817 0.159 Uiso calc 0.880(8) A 1
    H H17C 0.748986 0.572968 0.359468 0.159 Uiso calc 0.880(8) A 1
    C C16A 0.6613(11) 0.734(3) 0.308(2) 0.0730(10) Uani d 0.120(8) A 2
    H H16C 0.678136 0.768901 0.365371 0.088 Uiso calc 0.120(8) A 2
    H H16D 0.711080 0.787784 0.273674 0.088 Uiso calc 0.120(8) A 2
    C C17A 0.694(3) 0.573(3) 0.306(3) 0.1058(17) Uani d 0.120(8) A 2
    H H17D 0.768610 0.560942 0.332235 0.159 Uiso calc 0.120(8) A 2
    H H17E 0.689151 0.538366 0.248687 0.159 Uiso calc 0.120(8) A 2
    H H17F 0.643514 0.515141 0.336788 0.159 Uiso calc 0.120(8) A 2
_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
    S1 C9 . 1.7143(18) ?
    N1 C7 . 1.338(2) ?
    N1 C6 . 1.461(2) ?
    N1 H1A . 0.9100 ?
    N2 C9 . 1.328(2) ?
    N2 C1 . 1.463(2) ?
    N2 H2 . 0.9099 ?
    C1 C2 . 1.528(3) ?
    C1 C6 . 1.538(3) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.523(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.501(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.521(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.532(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6 . 0.9800 ?
    C7 C8 . 1.375(2) ?
    C7 C10 . 1.494(2) ?
    C8 C9 . 1.419(2) ?
    C8 H8 . 0.9300 ?
    C10 C11 . 1.389(3) ?
    C10 C15 . 1.393(3) ?
    C11 C12 . 1.387(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.376(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.369(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.388(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    O1 C16 . 1.416(3) ?
    O1 C16A . 1.416(4) ?
    O1 H1B . 0.8700 ?
    C16 C17 . 1.495(5) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C16A C17A . 1.495(6) ?
    C16A H16C . 0.9700 ?
    C16A H16D . 0.9700 ?
    C17A H17D . 0.9600 ?
    C17A H17E . 0.9600 ?
    C17A H17F . 0.9600 ?
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
    C7 N1 C6 . . 126.71(15) ?
    C7 N1 H1A . . 118.7 ?
    C6 N1 H1A . . 114.5 ?
    C9 N2 C1 . . 127.96(15) ?
    C9 N2 H2 . . 114.5 ?
    C1 N2 H2 . . 117.6 ?
    N2 C1 C2 . . 106.07(16) ?
    N2 C1 C6 . . 111.68(15) ?
    C2 C1 C6 . . 111.82(16) ?
    N2 C1 H1 . . 109.1 ?
    C2 C1 H1 . . 109.1 ?
    C6 C1 H1 . . 109.1 ?
    C3 C2 C1 . . 113.13(19) ?
    C3 C2 H2A . . 109.0 ?
    C1 C2 H2A . . 109.0 ?
    C3 C2 H2B . . 109.0 ?
    C1 C2 H2B . . 109.0 ?
    H2A C2 H2B . . 107.8 ?
    C4 C3 C2 . . 109.73(19) ?
    C4 C3 H3A . . 109.7 ?
    C2 C3 H3A . . 109.7 ?
    C4 C3 H3B . . 109.7 ?
    C2 C3 H3B . . 109.7 ?
    H3A C3 H3B . . 108.2 ?
    C3 C4 C5 . . 109.8(2) ?
    C3 C4 H4A . . 109.7 ?
    C5 C4 H4A . . 109.7 ?
    C3 C4 H4B . . 109.7 ?
    C5 C4 H4B . . 109.7 ?
    H4A C4 H4B . . 108.2 ?
    C4 C5 C6 . . 113.44(17) ?
    C4 C5 H5A . . 108.9 ?
    C6 C5 H5A . . 108.9 ?
    C4 C5 H5B . . 108.9 ?
    C6 C5 H5B . . 108.9 ?
    H5A C5 H5B . . 107.7 ?
    N1 C6 C5 . . 106.42(15) ?
    N1 C6 C1 . . 111.14(16) ?
    C5 C6 C1 . . 112.51(16) ?
    N1 C6 H6 . . 108.9 ?
    C5 C6 H6 . . 108.9 ?
    C1 C6 H6 . . 108.9 ?
    N1 C7 C8 . . 127.71(16) ?
    N1 C7 C10 . . 114.72(15) ?
    C8 C7 C10 . . 117.50(16) ?
    C7 C8 C9 . . 131.47(17) ?
    C7 C8 H8 . . 114.3 ?
    C9 C8 H8 . . 114.3 ?
    N2 C9 C8 . . 123.24(16) ?
    N2 C9 S1 . . 117.65(13) ?
    C8 C9 S1 . . 119.09(14) ?
    C11 C10 C15 . . 118.79(17) ?
    C11 C10 C7 . . 120.66(16) ?
    C15 C10 C7 . . 120.53(16) ?
    C12 C11 C10 . . 120.5(2) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C13 C12 C11 . . 120.1(2) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C14 C13 C12 . . 119.97(19) ?
    C14 C13 H13 . . 120.0 ?
    C12 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 120.6(2) ?
    C13 C14 H14 . . 119.7 ?
    C15 C14 H14 . . 119.7 ?
    C14 C15 C10 . . 120.0(2) ?
    C14 C15 H15 . . 120.0 ?
    C10 C15 H15 . . 120.0 ?
    C16 O1 H1B . . 107.3 ?
    C16A O1 H1B . . 124.5 ?
    O1 C16 C17 . . 107.7(3) ?
    O1 C16 H16A . . 110.2 ?
    C17 C16 H16A . . 110.2 ?
    O1 C16 H16B . . 110.2 ?
    C17 C16 H16B . . 110.2 ?
    H16A C16 H16B . . 108.5 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O1 C16A C17A . . 122(2) ?
    O1 C16A H16C . . 107.0 ?
    C17A C16A H16C . . 107.0 ?
    O1 C16A H16D . . 107.0 ?
    C17A C16A H16D . . 107.0 ?
    H16C C16A H16D . . 106.7 ?
    C16A C17A H17D . . 109.5 ?
    C16A C17A H17E . . 109.5 ?
    H17D C17A H17E . . 109.5 ?
    C16A C17A H17F . . 109.5 ?
    H17D C17A H17F . . 109.5 ?
    H17E C17A H17F . . 109.5 ?
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
    C9 N2 C1 C2 . . . . 176.7(2) ?
    C9 N2 C1 C6 . . . . 54.7(3) ?
    N2 C1 C2 C3 . . . . -172.9(2) ?
    C6 C1 C2 C3 . . . . -50.9(3) ?
    C1 C2 C3 C4 . . . . 58.6(3) ?
    C2 C3 C4 C5 . . . . -60.0(3) ?
    C3 C4 C5 C6 . . . . 56.8(3) ?
    C7 N1 C6 C5 . . . . 169.86(19) ?
    C7 N1 C6 C1 . . . . 47.0(3) ?
    C4 C5 C6 N1 . . . . -171.3(2) ?
    C4 C5 C6 C1 . . . . -49.4(3) ?
    N2 C1 C6 N1 . . . . -76.6(2) ?
    C2 C1 C6 N1 . . . . 164.69(17) ?
    N2 C1 C6 C5 . . . . 164.15(17) ?
    C2 C1 C6 C5 . . . . 45.5(2) ?
    C6 N1 C7 C8 . . . . -1.6(3) ?
    C6 N1 C7 C10 . . . . 175.40(17) ?
    N1 C7 C8 C9 . . . . -6.4(4) ?
    C10 C7 C8 C9 . . . . 176.8(2) ?
    C1 N2 C9 C8 . . . . -4.3(3) ?
    C1 N2 C9 S1 . . . . 174.38(15) ?
    C7 C8 C9 N2 . . . . -13.8(4) ?
    C7 C8 C9 S1 . . . . 167.52(18) ?
    N1 C7 C10 C11 . . . . 138.34(19) ?
    C8 C7 C10 C11 . . . . -44.4(3) ?
    N1 C7 C10 C15 . . . . -43.0(2) ?
    C8 C7 C10 C15 . . . . 134.25(19) ?
    C15 C10 C11 C12 . . . . -0.6(3) ?
    C7 C10 C11 C12 . . . . 178.09(19) ?
    C10 C11 C12 C13 . . . . -0.1(3) ?
    C11 C12 C13 C14 . . . . 0.8(4) ?
    C12 C13 C14 C15 . . . . -0.8(3) ?
    C13 C14 C15 C10 . . . . 0.1(3) ?
    C11 C10 C15 C14 . . . . 0.6(3) ?
    C7 C10 C15 C14 . . . . -178.09(18) ?
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 O1 . 0.91 2.13 3.030(2) 173 yes
    N2 H2 S1 3_566 0.91 2.53 3.4312(15) 171 yes
    O1 H1B S1 2 0.87 2.42 3.2886(18) 173 yes
    C6 H6 Cg2 2 0.98 2.54 3.516(2) 177 yes
