##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-04-11
_journal_date_accepted     2011-04-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      5
_journal_page_first     o1164
_journal_page_last     o1164
_journal_paper_category     QO
_journal_coeditor_code     HG5025
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
3-{(E)-[1-(2-Hydroxyphenyl)ethylidene]amino}-1-(2-methylphenyl)thiourea
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    ' Md. Abdus Salam ' .
;
Faculty of Resource Science and Technology, Universiti Malaysia Sarawak
94300 Kota Samarahan, Sarawak, Malaysia
;
    ' Md. Abu Affan '
;
Additional correspondence author, e-mail: maaffan@yahoo.com.
;
;
Faculty of Resource Science and Technology, Universiti Malaysia Sarawak
94300 Kota Samarahan, Sarawak, Malaysia
;
    ' Mohd. Razip Asaruddin ' .
;
Faculty of Resource Science and Technology, Universiti Malaysia Sarawak
94300 Kota Samarahan, Sarawak, Malaysia
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-{(E)-[1-(2-Hydroxyphenyl)ethylidene]amino}-1-(2-methylphenyl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H17 N3 O S'
_chemical_formula_sum     'C16 H17 N3 O S'
_chemical_formula_iupac     'C16 H17 N3 O S'
_chemical_formula_weight     299.39
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.6966(8)
_cell_length_b     7.3586(4)
_cell_length_c     14.0926(8)
_cell_angle_alpha     90.00
_cell_angle_beta     94.358(5)
_cell_angle_gamma     90.00
_cell_volume     1519.66(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1905
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     29.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light-yellow'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.309
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     0.215
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.419
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
;
Agilent Supernova Dual diffractometer with an Atlas detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     7614
_diffrn_reflns_av_R_equivalents     0.0659
_diffrn_reflns_av_sigmaI/netI     0.1060
_diffrn_reflns_theta_min     2.78
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.965
_diffrn_measured_fraction_theta_full     0.965
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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 >
2σ(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.
;
_reflns_number_total     3375
_reflns_number_gt     2094
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1110
_refine_ls_R_factor_gt     0.0599
_refine_ls_wR_factor_gt     0.1324
_refine_ls_wR_factor_ref     0.1738
_refine_ls_goodness_of_fit_ref     0.995
_refine_ls_restrained_S_all     0.995
_refine_ls_number_reflns     3375
_refine_ls_number_parameters     201
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0769P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_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     0.342
_refine_diff_density_min     -0.336
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                      'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.46230(5) 0.24817(10) 0.38597(5) 0.0188(2) Uani d . 1 1 . .
    O O1 0.21619(14) 0.2307(3) 0.31997(15) 0.0250(5) Uani d D 1 1 . .
    H H1O 0.2693(11) 0.261(4) 0.308(2) 0.038 Uiso d D 1 1 . .
    N N1 0.33770(15) 0.3710(3) 0.22261(17) 0.0182(6) Uani d . 1 1 . .
    N N2 0.42781(16) 0.4196(3) 0.21980(18) 0.0190(6) Uani d D 1 1 . .
    H H2N 0.4433(19) 0.497(3) 0.1764(16) 0.023 Uiso d D 1 1 . .
    N N3 0.57409(16) 0.4362(3) 0.27942(17) 0.0197(6) Uani d D 1 1 . .
    H H3N 0.5801(19) 0.496(4) 0.2259(13) 0.024 Uiso d D 1 1 . .
    C C1 0.1592(2) 0.2588(4) 0.2410(2) 0.0229(7) Uani d . 1 1 . .
    C C2 0.0685(2) 0.2066(5) 0.2458(3) 0.0309(8) Uani d . 1 1 . .
    H H2 0.0496 0.1544 0.3027 0.037 Uiso calc R 1 1 . .
    C C3 0.0062(2) 0.2298(5) 0.1692(3) 0.0331(9) Uani d . 1 1 . .
    H H3A -0.0553 0.1927 0.1732 0.040 Uiso calc R 1 1 . .
    C C4 0.0327(2) 0.3073(5) 0.0857(3) 0.0320(8) Uani d . 1 1 . .
    H H4 -0.0104 0.3236 0.0327 0.038 Uiso calc R 1 1 . .
    C C5 0.1220(2) 0.3603(4) 0.0806(2) 0.0260(8) Uani d . 1 1 . .
    H H5A 0.1396 0.4142 0.0236 0.031 Uiso calc R 1 1 . .
    C C6 0.18777(19) 0.3372(4) 0.1568(2) 0.0200(7) Uani d . 1 1 . .
    C C7 0.28345(19) 0.3879(4) 0.1464(2) 0.0189(7) Uani d . 1 1 . .
    C C8 0.3131(2) 0.4548(4) 0.0530(2) 0.0229(7) Uani d . 1 1 . .
    H H8A 0.3795 0.4432 0.0525 0.034 Uiso calc R 1 1 . .
    H H8B 0.2957 0.5827 0.0445 0.034 Uiso calc R 1 1 . .
    H H8C 0.2834 0.3824 0.0012 0.034 Uiso calc R 1 1 . .
    C C9 0.48965(19) 0.3751(4) 0.2920(2) 0.0174(7) Uani d . 1 1 . .
    C C10 0.65424(19) 0.4166(4) 0.3422(2) 0.0172(7) Uani d . 1 1 . .
    C C11 0.6563(2) 0.4776(4) 0.4351(2) 0.0201(7) Uani d . 1 1 . .
    H H11 0.6024 0.5242 0.4592 0.024 Uiso calc R 1 1 . .
    C C12 0.7355(2) 0.4712(4) 0.4928(2) 0.0252(7) Uani d . 1 1 . .
    H H12A 0.7364 0.5112 0.5570 0.030 Uiso calc R 1 1 . .
    C C13 0.8147(2) 0.4057(4) 0.4568(2) 0.0253(7) Uani d . 1 1 . .
    H H13 0.8703 0.4035 0.4960 0.030 Uiso calc R 1 1 . .
    C C14 0.8128(2) 0.3441(4) 0.3647(2) 0.0231(7) Uani d . 1 1 . .
    H H14 0.8671 0.2974 0.3414 0.028 Uiso calc R 1 1 . .
    C C15 0.73287(19) 0.3485(4) 0.3047(2) 0.0195(7) Uani d . 1 1 . .
    C C16 0.7318(2) 0.2841(4) 0.2034(2) 0.0260(8) Uani d . 1 1 . .
    H H16A 0.7815 0.1969 0.1974 0.039 Uiso calc R 1 1 . .
    H H16B 0.7401 0.3882 0.1615 0.039 Uiso calc R 1 1 . .
    H H16C 0.6733 0.2253 0.1851 0.039 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0225(4) 0.0163(4) 0.0179(4) -0.0009(3) 0.0039(3) -0.0001(3)
    O1 0.0214(11) 0.0291(13) 0.0247(13) -0.0029(10) 0.0027(10) -0.0005(10)
    N1 0.0150(12) 0.0148(13) 0.0247(15) -0.0010(10) 0.0019(10) -0.0010(11)
    N2 0.0179(13) 0.0166(14) 0.0222(15) -0.0023(10) 0.0002(11) 0.0044(11)
    N3 0.0187(13) 0.0205(14) 0.0199(15) -0.0006(11) 0.0016(11) 0.0052(11)
    C1 0.0245(16) 0.0172(16) 0.0269(18) 0.0046(13) 0.0018(13) -0.0085(14)
    C2 0.0234(17) 0.030(2) 0.040(2) -0.0028(14) 0.0098(15) -0.0020(16)
    C3 0.0198(17) 0.031(2) 0.049(2) -0.0018(14) 0.0039(16) -0.0077(17)
    C4 0.0248(18) 0.0298(19) 0.040(2) 0.0018(15) -0.0039(15) 0.0006(17)
    C5 0.0242(17) 0.0207(17) 0.032(2) 0.0010(14) -0.0026(14) -0.0014(15)
    C6 0.0174(15) 0.0158(16) 0.0266(18) -0.0010(12) 0.0003(13) -0.0037(13)
    C7 0.0209(15) 0.0104(15) 0.0250(18) 0.0038(12) 0.0004(13) -0.0030(13)
    C8 0.0248(16) 0.0192(17) 0.0247(18) -0.0002(13) 0.0021(13) -0.0036(14)
    C9 0.0180(15) 0.0151(15) 0.0197(16) 0.0034(12) 0.0045(12) -0.0028(13)
    C10 0.0185(15) 0.0126(15) 0.0205(17) -0.0006(12) 0.0014(12) 0.0014(12)
    C11 0.0272(16) 0.0095(14) 0.0239(18) 0.0015(13) 0.0045(13) -0.0009(13)
    C12 0.0354(19) 0.0158(16) 0.0235(18) -0.0033(14) -0.0037(14) 0.0013(14)
    C13 0.0249(17) 0.0192(17) 0.030(2) -0.0021(13) -0.0091(14) 0.0055(14)
    C14 0.0171(15) 0.0183(16) 0.034(2) 0.0001(13) 0.0034(13) 0.0026(15)
    C15 0.0262(16) 0.0132(15) 0.0200(17) -0.0058(13) 0.0063(13) -0.0003(13)
    C16 0.0275(17) 0.0240(18) 0.0276(19) -0.0018(14) 0.0094(14) -0.0020(14)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 . 1.694(3) ?
    O1 C1 . 1.357(4) ?
    O1 H1O . 0.842(10) ?
    N1 C7 . 1.295(4) ?
    N1 N2 . 1.375(3) ?
    N2 C9 . 1.352(4) ?
    N2 H2N . 0.880(10) ?
    N3 C9 . 1.344(3) ?
    N3 C10 . 1.426(4) ?
    N3 H3N . 0.882(10) ?
    C1 C2 . 1.394(4) ?
    C1 C6 . 1.411(4) ?
    C2 C3 . 1.372(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.390(5) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.376(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.400(4) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.473(4) ?
    C7 C8 . 1.500(4) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C10 C11 . 1.383(4) ?
    C10 C15 . 1.400(4) ?
    C11 C12 . 1.369(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.391(4) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.373(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.395(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.503(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
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 O1 H1O . . 108(2) ?
    C7 N1 N2 . . 119.0(2) ?
    C9 N2 N1 . . 120.6(2) ?
    C9 N2 H2N . . 119(2) ?
    N1 N2 H2N . . 119.3(19) ?
    C9 N3 C10 . . 127.7(2) ?
    C9 N3 H3N . . 115.6(19) ?
    C10 N3 H3N . . 116.7(19) ?
    O1 C1 C2 . . 116.8(3) ?
    O1 C1 C6 . . 123.2(3) ?
    C2 C1 C6 . . 120.0(3) ?
    C3 C2 C1 . . 120.8(3) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    C2 C3 C4 . . 120.2(3) ?
    C2 C3 H3A . . 119.9 ?
    C4 C3 H3A . . 119.9 ?
    C5 C4 C3 . . 119.4(3) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 122.1(3) ?
    C4 C5 H5A . . 119.0 ?
    C6 C5 H5A . . 119.0 ?
    C5 C6 C1 . . 117.6(3) ?
    C5 C6 C7 . . 120.1(3) ?
    C1 C6 C7 . . 122.3(3) ?
    N1 C7 C6 . . 115.1(3) ?
    N1 C7 C8 . . 123.9(3) ?
    C6 C7 C8 . . 120.9(3) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N3 C9 N2 . . 113.2(2) ?
    N3 C9 S1 . . 124.3(2) ?
    N2 C9 S1 . . 122.4(2) ?
    C11 C10 C15 . . 121.0(3) ?
    C11 C10 N3 . . 120.9(3) ?
    C15 C10 N3 . . 117.9(3) ?
    C12 C11 C10 . . 120.5(3) ?
    C12 C11 H11 . . 119.7 ?
    C10 C11 H11 . . 119.7 ?
    C11 C12 C13 . . 119.5(3) ?
    C11 C12 H12A . . 120.2 ?
    C13 C12 H12A . . 120.2 ?
    C14 C13 C12 . . 120.1(3) ?
    C14 C13 H13 . . 120.0 ?
    C12 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 121.5(3) ?
    C13 C14 H14 . . 119.3 ?
    C15 C14 H14 . . 119.3 ?
    C14 C15 C10 . . 117.4(3) ?
    C14 C15 C16 . . 121.1(3) ?
    C10 C15 C16 . . 121.5(3) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 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
    C7 N1 N2 C9 . . . . -168.5(3) ?
    O1 C1 C2 C3 . . . . -179.9(3) ?
    C6 C1 C2 C3 . . . . 0.3(5) ?
    C1 C2 C3 C4 . . . . -0.5(5) ?
    C2 C3 C4 C5 . . . . 0.1(5) ?
    C3 C4 C5 C6 . . . . 0.6(5) ?
    C4 C5 C6 C1 . . . . -0.8(5) ?
    C4 C5 C6 C7 . . . . 177.0(3) ?
    O1 C1 C6 C5 . . . . -179.4(3) ?
    C2 C1 C6 C5 . . . . 0.3(4) ?
    O1 C1 C6 C7 . . . . 2.8(5) ?
    C2 C1 C6 C7 . . . . -177.4(3) ?
    N2 N1 C7 C6 . . . . -178.4(2) ?
    N2 N1 C7 C8 . . . . 1.2(4) ?
    C5 C6 C7 N1 . . . . 176.2(3) ?
    C1 C6 C7 N1 . . . . -6.1(4) ?
    C5 C6 C7 C8 . . . . -3.4(4) ?
    C1 C6 C7 C8 . . . . 174.3(3) ?
    C10 N3 C9 N2 . . . . 178.6(3) ?
    C10 N3 C9 S1 . . . . -3.6(4) ?
    N1 N2 C9 N3 . . . . -178.5(2) ?
    N1 N2 C9 S1 . . . . 3.7(4) ?
    C9 N3 C10 C11 . . . . -56.4(4) ?
    C9 N3 C10 C15 . . . . 129.0(3) ?
    C15 C10 C11 C12 . . . . -0.5(4) ?
    N3 C10 C11 C12 . . . . -174.9(3) ?
    C10 C11 C12 C13 . . . . 1.1(4) ?
    C11 C12 C13 C14 . . . . -1.5(5) ?
    C12 C13 C14 C15 . . . . 1.2(5) ?
    C13 C14 C15 C10 . . . . -0.6(4) ?
    C13 C14 C15 C16 . . . . 178.8(3) ?
    C11 C10 C15 C14 . . . . 0.2(4) ?
    N3 C10 C15 C14 . . . . 174.8(3) ?
    C11 C10 C15 C16 . . . . -179.2(3) ?
    N3 C10 C15 C16 . . . . -4.6(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
    O1 H1o N1 . 0.842(10) 1.81(2) 2.551(3) 145(3)
    N2 H2n S1 2_655 0.880(10) 2.508(16) 3.323(2) 154(3)
    N3 H3n S1 2_655 0.882(10) 2.485(17) 3.286(3) 151(2)
    C8 H8b Cg1 2_655 0.98 2.59 3.501(3) 155
