##############################################################################
#                                                                            #
# 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.                                #
#                                                                            #
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data_global
_audit_creation_method     SHELXL-2014
_journal_date_recd_electronic     2016-07-01
_journal_date_accepted     2016-07-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue      8
_journal_page_first     1171
_journal_page_last     1175
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016011658
_journal_coeditor_code     SU5311
_publ_contact_author_name     'Devadasan Velmurugan'
_publ_contact_author_address
;  CAS in Crystallography and Biophysics
   University of madras
   Maraimalai campus(guindy campus)
   Chennai 600 025
   India
;
_publ_contact_author_email     'shirai2011@gmail.com'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;
Crystal structures of
2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(3-nitrophenyl)acetamide
monohydrate and
N-(2-chlorophenyl)-2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Subasri, S.'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'Timiri, Ajay Kumar'
;
      Department of Pharmaceutical Sciences
      Birla Institute of Technology
      Mesra
      Ranchi
      India
;
    'Barji, Nayan Sinha'
;
      Department of Pharmaceutical Sciences
      Birla Institute of Technology
      Mesra
      Ranchi
      India
;
    'Venkatesan Jayaprakash'
;
      Department of Pharmaceutical Sciences
      Birla Institute of Technology
      Mesra
      Ranchi
      India
;
    'Vijayan, Viswanathan'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'Devadasan Velmurugan'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
_publ_section_synopsis
;
In the title 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamides, both compounds
have a folded conformation about the methylene C atom of the thioacetamide
bridge, with the pyrimidine ring being inclined to the benzene ring by
56.18(6) and 67.84(6)°. In both molecules, there is an intramolecular
N---H...N hydrogen bond stabilizing the folded conformation.
;
data_I
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1494257'
_chemical_name_systematic
;
2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(3-nitrophenyl)acetamide
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 N6 O3 S, H2 O'
_chemical_formula_sum     'C12 H14 N6 O4 S'
_chemical_formula_iupac     'C12 H12 N6 O3 S, H2 O'
_chemical_formula_weight     338.35
_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     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     7.23260(10)
_cell_length_b     14.3442(2)
_cell_length_c     14.0940(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1462.19(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3265
_cell_measurement_theta_min     2.026
_cell_measurement_theta_max     28.317
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.537
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.253
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.785
_exptl_absorpt_correction_T_max     0.845
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART APEXII area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7912
_diffrn_reflns_av_R_equivalents     0.0207
_diffrn_reflns_theta_min     2.026
_diffrn_reflns_theta_max     28.317
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     18
_refine_special_details     ?
_reflns_number_total     3265
_reflns_number_gt     3034
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0304
_refine_ls_R_factor_gt     0.0271
_refine_ls_wR_factor_gt     0.0671
_refine_ls_wR_factor_ref     0.0693
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     3265
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0396P)²+0.1263P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.159
_refine_diff_density_min     -0.169
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0039(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
Flack x determined using 1217 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.07(3)
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
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
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 0.12955(8) 0.37215(3) 0.66439(4) 0.03810(14) Uani d 1 . .
    O O1 0.2112(3) 0.32497(11) 0.42274(13) 0.0555(5) Uani d 1 . .
    O O2 0.4515(3) 0.40381(12) 0.13791(14) 0.0570(5) Uani d 1 . .
    O O3 0.4586(3) 0.53670(14) 0.06709(14) 0.0602(5) Uani d 1 . .
    N N1 -0.0426(3) 0.69929(14) 0.58998(15) 0.0483(5) Uani d 1 . .
    H H1A -0.112(3) 0.6759(19) 0.550(2) 0.039(7) Uiso d 1 . .
    H H1B -0.049(4) 0.7564(18) 0.601(2) 0.048(7) Uiso d 1 . .
    N N2 0.2912(3) 0.62828(15) 0.87403(16) 0.0473(5) Uani d 1 . .
    H H2A 0.343(4) 0.587(2) 0.902(2) 0.052(9) Uiso d 1 . .
    H H2B 0.303(4) 0.683(2) 0.891(2) 0.058(8) Uiso d 1 . .
    N N3 0.2016(2) 0.51355(12) 0.77054(12) 0.0346(4) Uani d 1 . .
    N N4 0.0368(2) 0.54948(11) 0.62840(12) 0.0327(4) Uani d 1 . .
    N N5 0.1324(3) 0.47612(12) 0.44843(13) 0.0361(4) Uani d 1 . .
    H H5 0.081(4) 0.5115(19) 0.490(2) 0.050(7) Uiso d 1 . .
    N N6 0.4308(3) 0.48792(13) 0.13678(13) 0.0404(4) Uani d 1 . .
    C C1 0.0378(3) 0.64158(12) 0.65303(16) 0.0351(4) Uani d 1 . .
    C C2 0.1209(3) 0.67214(15) 0.73550(15) 0.0386(5) Uani d 1 . .
    H H2 0.1206 0.7349 0.7522 0.046 Uiso calc 1 . .
    C C3 0.2048(3) 0.60567(14) 0.79264(17) 0.0359(4) Uani d 1 . .
    C C4 0.1191(3) 0.49297(13) 0.68900(14) 0.0318(4) Uani d 1 . .
    C C5 0.0093(3) 0.36034(14) 0.55277(16) 0.0369(5) Uani d 1 . .
    H H5A -0.0345 0.2967 0.5466 0.044 Uiso calc 1 . .
    H H5B -0.0979 0.4010 0.5532 0.044 Uiso calc 1 . .
    C C6 0.1278(3) 0.38380(14) 0.46763(15) 0.0350(4) Uani d 1 . .
    C C7 0.2255(3) 0.52300(13) 0.37571(15) 0.0327(4) Uani d 1 . .
    C C8 0.2440(4) 0.61934(14) 0.38488(18) 0.0418(5) Uani d 1 . .
    H H8 0.2021 0.6488 0.4396 0.050 Uiso calc 1 . .
    C C9 0.3239(4) 0.67138(15) 0.31366(19) 0.0471(6) Uani d 1 . .
    H H9 0.3368 0.7355 0.3211 0.057 Uiso calc 1 . .
    C C10 0.3850(3) 0.62925(15) 0.23135(18) 0.0418(5) Uani d 1 . .
    H H10 0.4364 0.6640 0.1823 0.050 Uiso calc 1 . .
    C C11 0.3670(3) 0.53390(15) 0.22449(15) 0.0339(4) Uani d 1 . .
    C C12 0.2907(3) 0.47907(13) 0.29473(15) 0.0331(4) Uani d 1 . .
    H H12 0.2832 0.4147 0.2880 0.040 Uiso calc 1 . .
    O O1W 0.7494(3) 0.61566(15) 0.42859(15) 0.0615(5) Uani d 1 . .
    H H1WA 0.7637 0.5885 0.3748 0.092 Uiso d 1 . .
    H H1WB 0.6377 0.6003 0.4521 0.092 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
    S1 C4 . 1.769(2) ?
    S1 C5 . 1.805(2) ?
    O1 C6 . 1.215(3) ?
    O2 N6 . 1.216(2) ?
    O3 N6 . 1.223(3) ?
    N1 C1 . 1.347(3) ?
    N1 H1A . 0.83(3) ?
    N1 H1B . 0.84(3) ?
    N2 C3 . 1.346(3) ?
    N2 H2A . 0.80(3) ?
    N2 H2B . 0.83(3) ?
    N3 C4 . 1.328(3) ?
    N3 C3 . 1.358(3) ?
    N4 C4 . 1.319(3) ?
    N4 C1 . 1.366(2) ?
    N5 C6 . 1.352(3) ?
    N5 C7 . 1.398(3) ?
    N5 H5 . 0.86(3) ?
    N6 C11 . 1.475(3) ?
    C1 C2 . 1.380(3) ?
    C2 C3 . 1.388(3) ?
    C2 H2 . 0.9300 ?
    C5 C6 . 1.512(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C7 C12 . 1.386(3) ?
    C7 C8 . 1.394(3) ?
    C8 C9 . 1.378(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.381(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.377(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.380(3) ?
    C12 H12 . 0.9300 ?
    O1W H1WA . 0.8582 ?
    O1W H1WB . 0.9004 ?
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
    C4 S1 C5 . . 104.01(9) ?
    C1 N1 H1A . . 117.8(18) ?
    C1 N1 H1B . . 120(2) ?
    H1A N1 H1B . . 120(3) ?
    C3 N2 H2A . . 117(2) ?
    C3 N2 H2B . . 121(2) ?
    H2A N2 H2B . . 121(3) ?
    C4 N3 C3 . . 114.97(18) ?
    C4 N4 C1 . . 115.30(18) ?
    C6 N5 C7 . . 129.02(18) ?
    C6 N5 H5 . . 115.5(19) ?
    C7 N5 H5 . . 115.1(19) ?
    O2 N6 O3 . . 123.9(2) ?
    O2 N6 C11 . . 118.11(18) ?
    O3 N6 C11 . . 117.96(18) ?
    N1 C1 N4 . . 115.1(2) ?
    N1 C1 C2 . . 123.28(19) ?
    N4 C1 C2 . . 121.57(19) ?
    C1 C2 C3 . . 117.44(19) ?
    C1 C2 H2 . . 121.3 ?
    C3 C2 H2 . . 121.3 ?
    N2 C3 N3 . . 116.0(2) ?
    N2 C3 C2 . . 122.1(2) ?
    N3 C3 C2 . . 121.9(2) ?
    N4 C4 N3 . . 128.79(18) ?
    N4 C4 S1 . . 119.62(15) ?
    N3 C4 S1 . . 111.59(15) ?
    C6 C5 S1 . . 113.43(15) ?
    C6 C5 H5A . . 108.9 ?
    S1 C5 H5A . . 108.9 ?
    C6 C5 H5B . . 108.9 ?
    S1 C5 H5B . . 108.9 ?
    H5A C5 H5B . . 107.7 ?
    O1 C6 N5 . . 124.3(2) ?
    O1 C6 C5 . . 122.68(19) ?
    N5 C6 C5 . . 113.01(18) ?
    C12 C7 C8 . . 119.6(2) ?
    C12 C7 N5 . . 123.27(17) ?
    C8 C7 N5 . . 117.05(19) ?
    C9 C8 C7 . . 120.6(2) ?
    C9 C8 H8 . . 119.7 ?
    C7 C8 H8 . . 119.7 ?
    C8 C9 C10 . . 120.6(2) ?
    C8 C9 H9 . . 119.7 ?
    C10 C9 H9 . . 119.7 ?
    C11 C10 C9 . . 117.6(2) ?
    C11 C10 H10 . . 121.2 ?
    C9 C10 H10 . . 121.2 ?
    C10 C11 C12 . . 123.6(2) ?
    C10 C11 N6 . . 118.26(19) ?
    C12 C11 N6 . . 118.14(18) ?
    C11 C12 C7 . . 117.89(17) ?
    C11 C12 H12 . . 121.1 ?
    C7 C12 H12 . . 121.1 ?
    H1WA O1W H1WB . . 108.8 ?
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
    C4 N4 C1 N1 . . . . 178.57(19) ?
    C4 N4 C1 C2 . . . . 0.5(3) ?
    N1 C1 C2 C3 . . . . -177.6(2) ?
    N4 C1 C2 C3 . . . . 0.3(3) ?
    C4 N3 C3 N2 . . . . -178.7(2) ?
    C4 N3 C3 C2 . . . . 2.5(3) ?
    C1 C2 C3 N2 . . . . 179.3(2) ?
    C1 C2 C3 N3 . . . . -1.9(3) ?
    C1 N4 C4 N3 . . . . 0.3(3) ?
    C1 N4 C4 S1 . . . . -179.23(14) ?
    C3 N3 C4 N4 . . . . -1.7(3) ?
    C3 N3 C4 S1 . . . . 177.82(16) ?
    C5 S1 C4 N4 . . . . -0.85(19) ?
    C5 S1 C4 N3 . . . . 179.56(14) ?
    C4 S1 C5 C6 . . . . 81.31(16) ?
    C7 N5 C6 O1 . . . . 1.4(4) ?
    C7 N5 C6 C5 . . . . -179.6(2) ?
    S1 C5 C6 O1 . . . . 94.8(2) ?
    S1 C5 C6 N5 . . . . -84.2(2) ?
    C6 N5 C7 C12 . . . . 18.1(3) ?
    C6 N5 C7 C8 . . . . -164.9(2) ?
    C12 C7 C8 C9 . . . . 1.0(4) ?
    N5 C7 C8 C9 . . . . -176.0(2) ?
    C7 C8 C9 C10 . . . . 0.8(4) ?
    C8 C9 C10 C11 . . . . -1.5(4) ?
    C9 C10 C11 C12 . . . . 0.5(3) ?
    C9 C10 C11 N6 . . . . 179.7(2) ?
    O2 N6 C11 C10 . . . . 164.8(2) ?
    O3 N6 C11 C10 . . . . -15.6(3) ?
    O2 N6 C11 C12 . . . . -15.9(3) ?
    O3 N6 C11 C12 . . . . 163.6(2) ?
    C10 C11 C12 C7 . . . . 1.3(3) ?
    N6 C11 C12 C7 . . . . -177.94(17) ?
    C8 C7 C12 C11 . . . . -2.0(3) ?
    N5 C7 C12 C11 . . . . 174.86(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
    N5 H5 N4 . 0.86(3) 2.05(3) 2.832(3) 151(3)
    C12 H12 O1 . 0.93 2.35 2.911(3) 118
    N1 H1A O1W 1_455 0.83(3) 2.16(3) 2.979(3) 170(2)
    N1 H1B O2 3 0.84(3) 2.29(3) 3.082(3) 159(3)
    N2 H2A O3 1_556 0.80(3) 2.58(3) 3.255(3) 143(3)
    N2 H2B O1 3 0.83(3) 2.09(3) 2.904(3) 170(3)
    O1W H1WA N3 2_664 0.86 2.09 2.919(3) 162
    O1W H1WB O3 2_665 0.90 2.64 3.294(3) 130
_shelxl_version_number     2014/6
data_II
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1494258'
_chemical_name_systematic
;
N-(2-Chlorophenyl)-2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 Cl N5 O S'
_chemical_formula_sum     'C12 H12 Cl N5 O S'
_chemical_formula_iupac     'C12 H12 Cl N5 O S'
_chemical_formula_weight     309.78
_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     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.2528(2)
_cell_length_b     7.6249(3)
_cell_length_c     13.0649(4)
_cell_angle_alpha     91.410(2)
_cell_angle_beta     105.924(2)
_cell_angle_gamma     94.647(2)
_cell_volume     691.68(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2822
_cell_measurement_theta_min     1.623
_cell_measurement_theta_max     26.434
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.487
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     320
_exptl_absorpt_coefficient_mu     0.430
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_shelx_estimated_absorpt_T_min     0.882
_shelx_estimated_absorpt_T_max     0.919
_exptl_absorpt_correction_T_min     0.785
_exptl_absorpt_correction_T_max     0.845
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART APEXII area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10154
_diffrn_reflns_av_R_equivalents     0.0223
_diffrn_reflns_theta_min     1.623
_diffrn_reflns_theta_max     26.434
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     2822
_reflns_number_gt     2519
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0392
_refine_ls_R_factor_gt     0.0354
_refine_ls_wR_factor_gt     0.0957
_refine_ls_wR_factor_ref     0.0994
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     2822
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0515P)²+0.2692P] 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     0.499
_refine_diff_density_min     -0.496
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
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
    Cl Cl1 -0.32045(7) 0.83502(8) 0.11080(5) 0.06488(18) Uani d 1 . .
    S S1 0.22688(6) 0.44103(6) 0.41282(3) 0.04714(15) Uani d 1 . .
    O O1 0.35760(17) 0.81194(17) 0.26781(10) 0.0503(3) Uani d 1 . .
    N N1 -0.2505(3) -0.0531(2) 0.40354(14) 0.0541(4) Uani d 1 . .
    H H1A -0.163(3) -0.091(3) 0.4537(18) 0.051(6) Uiso d 1 . .
    H H1B -0.361(3) -0.101(3) 0.3829(18) 0.058(6) Uiso d 1 . .
    N N2 -0.4671(2) 0.4665(2) 0.23211(16) 0.0576(5) Uani d 1 . .
    H H2A -0.437(3) 0.572(3) 0.2321(18) 0.062(7) Uiso d 1 . .
    H H2B -0.584(4) 0.428(3) 0.2221(19) 0.070(7) Uiso d 1 . .
    N N3 -0.03937(19) 0.19020(19) 0.40540(10) 0.0396(3) Uani d 1 . .
    N N4 -0.14840(18) 0.44884(18) 0.31711(10) 0.0371(3) Uani d 1 . .
    N N5 0.0527(2) 0.6847(2) 0.20471(11) 0.0416(3) Uani d 1 . .
    H H5 -0.040(3) 0.631(3) 0.2233(15) 0.045(5) Uiso d 1 . .
    C C1 -0.2221(2) 0.1113(2) 0.37325(12) 0.0383(3) Uani d 1 . .
    C C2 -0.3723(2) 0.1992(2) 0.31353(13) 0.0403(4) Uani d 1 . .
    H H2 -0.4970 0.1447 0.2910 0.048 Uiso calc 1 . .
    C C3 -0.3310(2) 0.3694(2) 0.28860(13) 0.0378(3) Uani d 1 . .
    C C4 -0.0176(2) 0.3525(2) 0.37342(11) 0.0353(3) Uani d 1 . .
    C C5 0.2110(3) 0.6742(2) 0.39173(13) 0.0453(4) Uani d 1 . .
    H H5A 0.0924 0.7068 0.4045 0.054 Uiso calc 1 . .
    H H5B 0.3169 0.7396 0.4442 0.054 Uiso calc 1 . .
    C C6 0.2155(2) 0.7302(2) 0.28193(12) 0.0359(3) Uani d 1 . .
    C C7 0.0187(2) 0.7245(2) 0.09613(12) 0.0375(3) Uani d 1 . .
    C C8 -0.1521(2) 0.7917(2) 0.04306(14) 0.0428(4) Uani d 1 . .
    C C9 -0.1897(3) 0.8314(3) -0.06301(15) 0.0545(5) Uani d 1 . .
    H H9 -0.3048 0.8763 -0.0976 0.065 Uiso calc 1 . .
    C C10 -0.0557(4) 0.8039(3) -0.11667(15) 0.0603(6) Uani d 1 . .
    H H10 -0.0795 0.8312 -0.1879 0.072 Uiso calc 1 . .
    C C11 0.1148(3) 0.7360(3) -0.06546(15) 0.0556(5) Uani d 1 . .
    H H11 0.2048 0.7168 -0.1024 0.067 Uiso calc 1 . .
    C C12 0.1516(3) 0.6965(2) 0.04065(14) 0.0454(4) Uani d 1 . .
    H H12 0.2665 0.6508 0.0748 0.055 Uiso calc 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
    Cl1 C8 . 1.7397(19) ?
    S1 C4 . 1.7753(15) ?
    S1 C5 . 1.8135(19) ?
    O1 C6 . 1.2207(19) ?
    N1 C1 . 1.340(2) ?
    N1 H1A . 0.85(2) ?
    N1 H1B . 0.83(2) ?
    N2 C3 . 1.346(2) ?
    N2 H2A . 0.81(3) ?
    N2 H2B . 0.85(3) ?
    N3 C4 . 1.327(2) ?
    N3 C1 . 1.359(2) ?
    N4 C4 . 1.318(2) ?
    N4 C3 . 1.360(2) ?
    N5 C6 . 1.340(2) ?
    N5 C7 . 1.417(2) ?
    N5 H5 . 0.85(2) ?
    C1 C2 . 1.386(2) ?
    C2 C3 . 1.375(2) ?
    C2 H2 . 0.9300 ?
    C5 C6 . 1.515(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C7 C12 . 1.382(2) ?
    C7 C8 . 1.388(2) ?
    C8 C9 . 1.383(3) ?
    C9 C10 . 1.371(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.382(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.384(3) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 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
    C4 S1 C5 . . 103.22(8) ?
    C1 N1 H1A . . 118.4(15) ?
    C1 N1 H1B . . 116.7(16) ?
    H1A N1 H1B . . 123(2) ?
    C3 N2 H2A . . 116.6(17) ?
    C3 N2 H2B . . 118.0(17) ?
    H2A N2 H2B . . 120(2) ?
    C4 N3 C1 . . 115.11(13) ?
    C4 N4 C3 . . 114.72(13) ?
    C6 N5 C7 . . 125.63(14) ?
    C6 N5 H5 . . 116.8(13) ?
    C7 N5 H5 . . 117.5(13) ?
    N1 C1 N3 . . 117.08(15) ?
    N1 C1 C2 . . 121.83(15) ?
    N3 C1 C2 . . 121.08(14) ?
    C3 C2 C1 . . 117.94(14) ?
    C3 C2 H2 . . 121.0 ?
    C1 C2 H2 . . 121.0 ?
    N2 C3 N4 . . 115.59(15) ?
    N2 C3 C2 . . 122.48(15) ?
    N4 C3 C2 . . 121.90(15) ?
    N4 C4 N3 . . 129.18(14) ?
    N4 C4 S1 . . 118.71(12) ?
    N3 C4 S1 . . 112.10(11) ?
    C6 C5 S1 . . 115.29(12) ?
    C6 C5 H5A . . 108.5 ?
    S1 C5 H5A . . 108.5 ?
    C6 C5 H5B . . 108.5 ?
    S1 C5 H5B . . 108.5 ?
    H5A C5 H5B . . 107.5 ?
    O1 C6 N5 . . 124.20(15) ?
    O1 C6 C5 . . 121.24(15) ?
    N5 C6 C5 . . 114.56(14) ?
    C12 C7 C8 . . 118.68(15) ?
    C12 C7 N5 . . 121.45(15) ?
    C8 C7 N5 . . 119.87(15) ?
    C9 C8 C7 . . 121.22(18) ?
    C9 C8 Cl1 . . 118.54(15) ?
    C7 C8 Cl1 . . 120.20(13) ?
    C10 C9 C8 . . 119.36(19) ?
    C10 C9 H9 . . 120.3 ?
    C8 C9 H9 . . 120.3 ?
    C9 C10 C11 . . 120.31(17) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C10 C11 C12 . . 120.09(19) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C7 C12 C11 . . 120.34(18) ?
    C7 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
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
    C4 N3 C1 N1 . . . . 179.80(16) ?
    C4 N3 C1 C2 . . . . -1.4(2) ?
    N1 C1 C2 C3 . . . . 178.13(17) ?
    N3 C1 C2 C3 . . . . -0.6(3) ?
    C4 N4 C3 N2 . . . . 179.24(16) ?
    C4 N4 C3 C2 . . . . -2.5(2) ?
    C1 C2 C3 N2 . . . . -179.19(18) ?
    C1 C2 C3 N4 . . . . 2.7(3) ?
    C3 N4 C4 N3 . . . . 0.3(2) ?
    C3 N4 C4 S1 . . . . 178.72(11) ?
    C1 N3 C4 N4 . . . . 1.7(2) ?
    C1 N3 C4 S1 . . . . -176.86(11) ?
    C5 S1 C4 N4 . . . . 15.56(15) ?
    C5 S1 C4 N3 . . . . -165.73(12) ?
    C4 S1 C5 C6 . . . . -89.86(13) ?
    C7 N5 C6 O1 . . . . -0.6(3) ?
    C7 N5 C6 C5 . . . . 178.60(16) ?
    S1 C5 C6 O1 . . . . -106.66(16) ?
    S1 C5 C6 N5 . . . . 74.10(18) ?
    C6 N5 C7 C12 . . . . 47.4(2) ?
    C6 N5 C7 C8 . . . . -133.27(18) ?
    C12 C7 C8 C9 . . . . -0.5(2) ?
    N5 C7 C8 C9 . . . . -179.80(15) ?
    C12 C7 C8 Cl1 . . . . -178.14(12) ?
    N5 C7 C8 Cl1 . . . . 2.5(2) ?
    C7 C8 C9 C10 . . . . 0.0(3) ?
    Cl1 C8 C9 C10 . . . . 177.71(14) ?
    C8 C9 C10 C11 . . . . 0.5(3) ?
    C9 C10 C11 C12 . . . . -0.5(3) ?
    C8 C7 C12 C11 . . . . 0.5(2) ?
    N5 C7 C12 C11 . . . . 179.79(15) ?
    C10 C11 C12 C7 . . . . 0.0(3) ?
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
    N5 H5 N4 . 0.85(2) 2.12(2) 2.898(2) 152(2)
    N2 H2A Cl1 . 0.81(3) 2.81(2) 3.493(2) 143(2)
    N1 H1A N3 2_556 0.85(2) 2.21(2) 3.058(2) 174(2)
    N1 H1B O1 1_445 0.83(2) 2.21(2) 2.992(2) 157(2)
    N2 H2A O1 1_455 0.81(3) 2.56(2) 3.095(2) 124(2)
    C2 H2 O1 1_445 0.93 2.64 3.353(2) 134
_shelxl_version_number     2014/6
