##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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. The current version number is 2.0.1.  #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     99-01-26
_journal_date_accepted     99-04-26
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     AUG99
_journal_page_first     1318
_journal_page_last     1320
_journal_paper_category     FO
_publ_contact_author_name     'Dr D. Velmurugan'
_publ_contact_author_address
;
Department of Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
_publ_contact_author_email     velu@cyberspace.org
_publ_contact_author_fax     '91 44 2352494'
_publ_contact_author_phone     '91 44 2300122'
_publ_section_title
;
N---H...S hydrogen bonding in N-benzoyl-N'-methyl-N'-phenylthiourea  and
N-benzoyl-N'-(3,4-dimethylphenyl)thiourea
;
loop_
    _publ_author_name
    _publ_author_address
    'S. Shanmuga Sundara Raj'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'K. Puviarasan'
;
Department of Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'D. Velmurugan'
;
Department of Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'G. Jayanthi'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Hoong-Kun Fun'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-Benzoyl-N'-methyl-N'-phenyl thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C15 H14 N2 O S'
_chemical_formula_weight     270.34
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.4551(2)
_cell_length_b     8.9044(2)
_cell_length_c     10.7293(3)
_cell_angle_alpha     91.1420(10)
_cell_angle_beta     107.4370(10)
_cell_angle_gamma     113.0350(10)
_cell_volume     700.50(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8192
_cell_measurement_theta_min     2.01
_cell_measurement_theta_max     28.29
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.282
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     284
_exptl_absorpt_coefficient_mu     0.224
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.900
_exptl_absorpt_correction_T_max     0.957
_exptl_special_details
;
The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 30s covered 0.3° in ω.
The crystal-to-detector distance was 3 cm and the detector swing angle was
-40°. Coverage of the unique set is 95% and 98% complete for I and II
respectively. Crystal decay was
monitored by repeating thirty initial frames at the end of data collection
and analysing the duplicate reflections, and was found  to be negligible.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     5735
_diffrn_reflns_av_R_equivalents     0.049
_diffrn_reflns_av_sigmaI/netI     0.0753
_diffrn_reflns_theta_min     2.01
_diffrn_reflns_theta_max     28.32
_diffrn_reflns_theta_full     28.32
_diffrn_measured_fraction_theta_max     0.955
_diffrn_measured_fraction_theta_full     0.955
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3325
_reflns_number_gt     2219
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.069
_refine_ls_R_factor_gt     0.041
_refine_ls_wR_factor_ref     0.104
_refine_ls_goodness_of_fit_ref     0.925
_refine_ls_restrained_S_all     0.925
_refine_ls_number_reflns     3325
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0351P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.276
_refine_diff_density_min     -0.279
_refine_ls_extinction_method     SHELXTL
_refine_ls_extinction_coef     0.016(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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1996a)'
_computing_cell_refinement     'SAINT (Siemens, 1996b)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     'SHELXTL and PARST (Nardelli, 1995)'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 0.08796(7) 0.88241(6) 0.16300(4) 0.05847(18) Uani d . 1 . . S
    O1 -0.18736(17) 1.09165(15) 0.31387(11) 0.0555(3) Uani d . 1 . . O
    N1 -0.02898(19) 1.11811(16) 0.17158(12) 0.0417(3) Uani d . 1 . . N
    N2 0.18765(19) 1.11405(15) 0.36492(12) 0.0426(3) Uani d . 1 . . N
    C1 -0.2754(2) 1.20662(17) 0.12122(14) 0.0413(4) Uani d . 1 . . C
    C2 -0.4518(3) 1.1629(2) 0.11916(19) 0.0547(5) Uani d . 1 . . C
    C3 -0.5638(3) 1.2214(3) 0.0323(2) 0.0723(7) Uani d . 1 . . C
    C4 -0.4999(4) 1.3225(3) -0.0513(2) 0.0851(8) Uani d . 1 . . C
    C5 -0.3235(5) 1.3702(3) -0.0481(2) 0.0878(8) Uani d . 1 . . C
    C6 -0.2080(3) 1.3133(2) 0.03949(19) 0.0600(5) Uani d . 1 . . C
    C7 -0.1625(2) 1.13462(18) 0.21242(14) 0.0401(3) Uani d . 1 . . C
    C8 0.0846(2) 1.04516(18) 0.24039(14) 0.0411(4) Uani d . 1 . . C
    C9 0.2078(2) 1.26935(18) 0.42559(15) 0.0429(4) Uani d . 1 . . C
    C10 0.1792(3) 1.2794(2) 0.54485(16) 0.0526(4) Uani d . 1 . . C
    C11 0.2001(3) 1.4289(3) 0.6031(2) 0.0652(5) Uani d . 1 . . C
    C12 0.2470(3) 1.5664(3) 0.5417(2) 0.0718(6) Uani d . 1 . . C
    C13 0.2772(3) 1.5555(2) 0.4241(2) 0.0684(6) Uani d . 1 . . C
    C14 0.2614(3) 1.4086(2) 0.36611(17) 0.0527(4) Uani d . 1 . . C
    C15 0.3026(3) 1.0372(3) 0.44303(19) 0.0535(5) Uani d . 1 . . C
    H2 -0.496(3) 1.091(3) 0.169(2) 0.076(7) Uiso d . 1 . . H
    H3 -0.681(4) 1.193(3) 0.031(2) 0.092(8) Uiso d . 1 . . H
    H4 -0.578(3) 1.368(2) -0.110(2) 0.087(7) Uiso d . 1 . . H
    H5 -0.279(4) 1.433(3) -0.100(3) 0.107(9) Uiso d . 1 . . H
    H6 -0.088(3) 1.343(2) 0.0422(18) 0.056(5) Uiso d . 1 . . H
    H10 0.143(3) 1.180(2) 0.5865(17) 0.061(5) Uiso d . 1 . . H
    H11 0.182(3) 1.432(2) 0.689(2) 0.076(6) Uiso d . 1 . . H
    H12 0.258(3) 1.667(2) 0.581(2) 0.075(6) Uiso d . 1 . . H
    H13 0.310(3) 1.648(3) 0.382(2) 0.083(7) Uiso d . 1 . . H
    H14 0.292(2) 1.403(2) 0.2911(17) 0.052(5) Uiso d . 1 . . H
    H15A 0.231(3) 0.925(2) 0.4410(18) 0.064(6) Uiso d . 1 . . H
    H15B 0.357(3) 1.095(2) 0.529(2) 0.061(5) Uiso d . 1 . . H
    H15C 0.390(3) 1.046(2) 0.405(2) 0.077(7) Uiso d . 1 . . H
    H1N1 -0.045(2) 1.1101(19) 0.0915(17) 0.046(5) Uiso d . 1 . . H
_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 C8 . 1.670(2) y
    O1 C7 . 1.2101(2) y
    N1 C7 . 1.383(2) ?
    N1 C8 . 1.404(2) y
    N1 H1N1 . 0.83(2) ?
    N2 C8 . 1.331(2) y
    N2 C9 . 1.442(2) y
    N2 C15 . 1.473(2) y
    C1 C2 . 1.379(3) ?
    C1 C6 . 1.380(2) ?
    C1 C7 . 1.4910(18) ?
    C2 C3 . 1.384(3) ?
    C2 H2 . 0.88(2) ?
    C3 C4 . 1.359(4) ?
    C3 H3 . 0.92(3) ?
    C4 C5 . 1.371(4) ?
    C4 H4 . 0.98(2) ?
    C5 C6 . 1.396(3) ?
    C5 H5 . 0.86(3) ?
    C6 H6 . 0.93(2) ?
    C9 C10 . 1.379(2) ?
    C9 C14 . 1.384(2) ?
    C10 C11 . 1.383(3) ?
    C10 H10 . 0.979(17) ?
    C11 C12 . 1.378(3) ?
    C11 H11 . 0.97(2) ?
    C12 C13 . 1.369(3) ?
    C12 H12 . 0.94(2) ?
    C13 C14 . 1.377(3) ?
    C13 H13 . 0.93(2) ?
    C14 H14 . 0.921(18) ?
    C15 H15A . 0.94(2) ?
    C15 H15B . 0.94(2) ?
    C15 H15C . 0.92(2) ?
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 C8 . . 123.49(13) y
    C7 N1 H1N1 . . 117.7(12) ?
    C8 N1 H1N1 . . 113.2(11) ?
    C8 N2 C9 . . 123.92(11) y
    C8 N2 C15 . . 118.87(14) ?
    C9 N2 C15 . . 116.94(13) ?
    C2 C1 C6 . . 120.07(16) ?
    C2 C1 C7 . . 118.24(15) ?
    C6 C1 C7 . . 121.69(16) ?
    C1 C2 C3 . . 120.2(2) ?
    C1 C2 H2 . . 119.6(14) ?
    C3 C2 H2 . . 120.0(14) ?
    C4 C3 C2 . . 120.0(2) ?
    C4 C3 H3 . . 119.8(14) ?
    C2 C3 H3 . . 120.3(14) ?
    C3 C4 C5 . . 120.46(19) ?
    C3 C4 H4 . . 120.0(14) ?
    C5 C4 H4 . . 119.4(14) ?
    C4 C5 C6 . . 120.4(2) ?
    C4 C5 H5 . . 122.8(18) ?
    C6 C5 H5 . . 116.7(18) ?
    C1 C6 C5 . . 118.8(2) ?
    C1 C6 H6 . . 119.4(10) ?
    C5 C6 H6 . . 121.7(11) ?
    O1 C7 N1 . . 122.38(13) ?
    O1 C7 C1 . . 122.57(16) y
    N1 C7 C1 . . 115.04(13) ?
    N2 C8 N1 . . 116.93(13) y
    N2 C8 S1 . . 123.66(10) ?
    N1 C8 S1 . . 119.39(11) ?
    C10 C9 C14 . . 120.35(16) ?
    C10 C9 N2 . . 119.73(14) ?
    C14 C9 N2 . . 119.89(15) ?
    C9 C10 C11 . . 119.50(17) ?
    C9 C10 H10 . . 119.5(11) ?
    C11 C10 H10 . . 121.0(11) ?
    C12 C11 C10 . . 120.2(2) ?
    C12 C11 H11 . . 122.7(11) ?
    C10 C11 H11 . . 117.0(11) ?
    C13 C12 C11 . . 119.77(19) ?
    C13 C12 H12 . . 120.4(13) ?
    C11 C12 H12 . . 119.9(13) ?
    C12 C13 C14 . . 120.8(2) ?
    C12 C13 H13 . . 120.2(13) ?
    C14 C13 H13 . . 118.9(14) ?
    C13 C14 C9 . . 119.23(19) ?
    C13 C14 H14 . . 121.3(10) ?
    C9 C14 H14 . . 119.4(10) ?
    N2 C15 H15A . . 109.6(11) ?
    N2 C15 H15B . . 107.4(10) ?
    H15A C15 H15B . . 111.5(16) ?
    N2 C15 H15C . . 107.9(12) ?
    H15A C15 H15C . . 109.4(17) ?
    H15B C15 H15C . . 110.9(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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 H1N1 S1 . . 2_575 0.83(2) 2.65(2) 3.4730(10)
                                                  174(2) yes
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-Benzoyl-N'-(3,4-dimethylphenyl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C16 H16 N2 O S'
_chemical_formula_weight     284.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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     5.46640(10)
_cell_length_b     28.0208(4)
_cell_length_c     9.85850(10)
_cell_angle_alpha     90.00
_cell_angle_beta     94.2620(10)
_cell_angle_gamma     90.00
_cell_volume     1505.88(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8192
_cell_measurement_theta_min     1.45
_cell_measurement_theta_max     28.33
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.254
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.212
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.913
_exptl_absorpt_correction_T_max     0.983
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     11799
_diffrn_reflns_av_R_equivalents     0.072
_diffrn_reflns_av_sigmaI/netI     0.0639
_diffrn_reflns_theta_min     1.45
_diffrn_reflns_theta_max     28.28
_diffrn_reflns_theta_full     28.28
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     37
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3688
_reflns_number_gt     2555
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.077
_refine_ls_R_factor_gt     0.053
_refine_ls_wR_factor_ref     0.165
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.057
_refine_ls_number_reflns     3688
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0958P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.396
_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     'SMART (Siemens, 1996a)'
_computing_cell_refinement     'SAINT (Siemens, 1996b)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     'SHELXTL and PARST (Nardelli, 1995)'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 0.32161(12) 0.546924(18) 0.86252(5) 0.0584(2) Uani d . 1 . . S
    O1 0.5611(3) 0.64283(5) 1.21950(16) 0.0629(5) Uani d . 1 . . O
    N1 0.5583(3) 0.57492(6) 1.09085(15) 0.0418(4) Uani d . 1 . . N
    N2 0.2799(3) 0.62930(6) 0.99591(16) 0.0451(4) Uani d D 1 . . N
    C1 0.8517(3) 0.58266(7) 1.28828(19) 0.0428(4) Uani d . 1 . . C
    C2 0.8819(5) 0.60021(9) 1.4207(2) 0.0618(6) Uani d . 1 . . C
    C3 1.0712(5) 0.58351(12) 1.5077(3) 0.0765(8) Uani d . 1 . . C
    C4 1.2289(5) 0.54928(11) 1.4650(3) 0.0722(8) Uani d . 1 . . C
    C5 1.2012(4) 0.53211(10) 1.3346(3) 0.0602(6) Uani d . 1 . . C
    C6 1.0124(4) 0.54886(8) 1.2454(2) 0.0473(5) Uani d . 1 . . C
    C7 0.6466(4) 0.60303(6) 1.19847(19) 0.0436(4) Uani d . 1 . . C
    C8 0.3816(3) 0.58639(6) 0.98713(17) 0.0387(4) Uani d . 1 . . C
    C9 0.1102(3) 0.65195(7) 0.90008(18) 0.0423(4) Uani d . 1 . . C
    C10 -0.0982(4) 0.62941(8) 0.8434(2) 0.0502(5) Uani d . 1 . . C
    C11 -0.2553(4) 0.65508(9) 0.7524(2) 0.0589(6) Uani d . 1 . . C
    C12 -0.2115(4) 0.70214(9) 0.7186(2) 0.0576(6) Uani d . 1 . . C
    C13 -0.0060(4) 0.72523(8) 0.7802(2) 0.0558(5) Uani d . 1 . . C
    C14 0.1538(4) 0.69958(7) 0.8696(2) 0.0489(5) Uani d . 1 . . C
    C15 -0.3827(6) 0.72724(13) 0.6141(3) 0.0915(10) Uani d . 1 . . C
    H15A -0.3272 0.7594 0.6023 0.137 Uiso calc R 1 . . H
    H15B -0.5454 0.7277 0.6446 0.137 Uiso calc R 1 . . H
    H15C -0.3841 0.7106 0.5290 0.137 Uiso calc R 1 . . H
    C16 0.0465(6) 0.77692(9) 0.7526(3) 0.0875(9) Uani d . 1 . . C
    H16A -0.0793 0.7895 0.6894 0.131 Uiso calc R 1 . . H
    H16B 0.2027 0.7796 0.7146 0.131 Uiso calc R 1 . . H
    H16C 0.0498 0.7946 0.8361 0.131 Uiso calc R 1 . . H
    H2 0.760(5) 0.6243(10) 1.455(3) 0.079(8) Uiso d . 1 . . H
    H3 1.080(6) 0.5950(11) 1.583(3) 0.094(10) Uiso d . 1 . . H
    H4 1.369(6) 0.5386(10) 1.515(3) 0.093(9) Uiso d . 1 . . H
    H5 1.311(5) 0.5059(11) 1.313(3) 0.086(9) Uiso d . 1 . . H
    H6 1.007(4) 0.5404(7) 1.160(2) 0.047(6) Uiso d . 1 . . H
    H10 -0.132(4) 0.5970(8) 0.864(2) 0.045(5) Uiso d . 1 . . H
    H11 -0.405(5) 0.6371(9) 0.713(2) 0.068(7) Uiso d . 1 . . H
    H14 0.309(4) 0.7135(8) 0.903(2) 0.054(6) Uiso d . 1 . . H
    H1N1 0.611(5) 0.5471(8) 1.090(3) 0.056(7) Uiso d . 1 . . H
    H1N2 0.341(4) 0.6448(8) 1.058(2) 0.055(7) Uiso d D 1 . . H
_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 C8 . 1.667(2) y
    O1 C7 . 1.233(2) y
    N1 C7 . 1.380(2) y
    N1 C8 . 1.391(2) y
    N1 H1N1 . 0.83(2) ?
    N2 C8 . 1.330(2) y
    N2 C9 . 1.423(2) y
    N2 H1N2 . 0.80(2) y
    C1 C6 . 1.379(3) ?
    C1 C2 . 1.393(3) ?
    C1 C7 . 1.490(2) ?
    C2 C3 . 1.376(3) ?
    C2 H2 . 1.02(3) ?
    C3 C4 . 1.376(4) ?
    C3 H3 . 0.81(3) ?
    C4 C5 . 1.370(4) ?
    C4 H4 . 0.93(3) ?
    C5 C6 . 1.387(3) ?
    C5 H5 . 0.98(3) ?
    C6 H6 . 0.87(2) ?
    C9 C10 . 1.384(3) ?
    C9 C14 . 1.392(3) ?
    C10 C11 . 1.395(3) ?
    C10 H10 . 0.95(2) ?
    C11 C12 . 1.385(4) ?
    C11 H11 . 1.01(2) ?
    C12 C13 . 1.395(3) ?
    C12 C15 . 1.513(3) ?
    C13 C14 . 1.393(3) ?
    C13 C16 . 1.505(3) ?
    C14 H14 . 0.97(2) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 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 C8 . . 128.15(16) y
    C7 N1 H1N1 . . 116.1(18) ?
    C8 N1 H1N1 . . 115.6(18) ?
    C8 N2 C9 . . 127.94(16) y
    C8 N2 H1N2 . . 112.6(16) ?
    C9 N2 H1N2 . . 118.7(16) ?
    C6 C1 C2 . . 119.70(18) ?
    C6 C1 C7 . . 123.33(17) ?
    C2 C1 C7 . . 116.95(18) ?
    C3 C2 C1 . . 119.7(2) ?
    C3 C2 H2 . . 119.7(15) ?
    C1 C2 H2 . . 120.5(15) ?
    C2 C3 C4 . . 120.4(2) ?
    C2 C3 H3 . . 115(2) ?
    C4 C3 H3 . . 124(2) ?
    C5 C4 C3 . . 120.2(2) ?
    C5 C4 H4 . . 114(2) ?
    C3 C4 H4 . . 125(2) ?
    C4 C5 C6 . . 120.1(2) ?
    C4 C5 H5 . . 116.1(17) ?
    C6 C5 H5 . . 123.6(17) ?
    C1 C6 C5 . . 119.9(2) ?
    C1 C6 H6 . . 120.4(14) ?
    C5 C6 H6 . . 119.3(15) ?
    O1 C7 N1 . . 122.03(17) ?
    O1 C7 C1 . . 121.66(17) y
    N1 C7 C1 . . 116.31(16) ?
    N2 C8 N1 . . 115.57(15) y
    N2 C8 S1 . . 125.97(13) ?
    N1 C8 S1 . . 118.43(13) ?
    C10 C9 C14 . . 119.94(18) ?
    C10 C9 N2 . . 122.75(18) ?
    C14 C9 N2 . . 117.21(17) ?
    C9 C10 C11 . . 118.3(2) ?
    C9 C10 H10 . . 121.3(12) ?
    C11 C10 H10 . . 120.5(12) ?
    C12 C11 C10 . . 122.4(2) ?
    C12 C11 H11 . . 121.9(14) ?
    C10 C11 H11 . . 115.7(14) ?
    C11 C12 C13 . . 119.01(18) ?
    C11 C12 C15 . . 119.8(2) ?
    C13 C12 C15 . . 121.2(2) ?
    C14 C13 C12 . . 118.8(2) ?
    C14 C13 C16 . . 119.5(2) ?
    C12 C13 C16 . . 121.7(2) ?
    C9 C14 C13 . . 121.5(2) ?
    C9 C14 H14 . . 118.1(14) ?
    C13 C14 H14 . . 120.0(14) ?
    C12 C15 H15A . . 109.5 ?
    C12 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C12 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 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
    C6 C1 C2 C3 . . . . -0.3(4) ?
    C7 C1 C2 C3 . . . . -178.7(2) ?
    C1 C2 C3 C4 . . . . -0.6(5) ?
    C2 C3 C4 C5 . . . . 1.1(5) ?
    C3 C4 C5 C6 . . . . -0.6(4) ?
    C2 C1 C6 C5 . . . . 0.8(3) ?
    C7 C1 C6 C5 . . . . 179.0(2) ?
    C4 C5 C6 C1 . . . . -0.3(4) ?
    C8 N1 C7 O1 . . . . 4.8(3) ?
    C8 N1 C7 C1 . . . . -175.17(18) ?
    C6 C1 C7 O1 . . . . -154.6(2) ?
    C2 C1 C7 O1 . . . . 23.7(3) ?
    C6 C1 C7 N1 . . . . 25.4(3) ?
    C2 C1 C7 N1 . . . . -156.3(2) ?
    C9 N2 C8 N1 . . . . 174.61(19) ?
    C9 N2 C8 S1 . . . . -3.5(3) ?
    C7 N1 C8 N2 . . . . -2.4(3) ?
    C7 N1 C8 S1 . . . . 175.82(16) ?
    C8 N2 C9 C10 . . . . 48.9(3) ?
    C8 N2 C9 C14 . . . . -134.6(2) ?
    C14 C9 C10 C11 . . . . 2.4(3) ?
    N2 C9 C10 C11 . . . . 178.78(19) ?
    C9 C10 C11 C12 . . . . -0.9(3) ?
    C10 C11 C12 C13 . . . . -1.6(4) ?
    C10 C11 C12 C15 . . . . 177.1(2) ?
    C11 C12 C13 C14 . . . . 2.6(3) ?
    C15 C12 C13 C14 . . . . -176.1(2) ?
    C11 C12 C13 C16 . . . . -177.4(2) ?
    C15 C12 C13 C16 . . . . 4.0(4) ?
    C10 C9 C14 C13 . . . . -1.4(3) ?
    N2 C9 C14 C13 . . . . -178.01(19) ?
    C12 C13 C14 C9 . . . . -1.1(3) ?
    C16 C13 C14 C9 . . . . 178.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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 H1N2 O1 . . 1_555 0.80(2) 1.92(2) 2.619(2) 145(2) yes
    C10 H10 S1 . . 1_555 0.95(2) 2.85(2) 3.253(2) 107(2) yes
    N1 H1N1 S1 . . 3_667 0.83(2) 2.70(2) 3.501(2) 163(3) yes
