# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c2c
#TrackingRef 'C2c.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'2-(4-methoxyphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.1942(13)
_cell_length_b                   13.4679(13)
_cell_length_c                   12.8940(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.384(7)
_cell_angle_gamma                90.00
_cell_volume                     2279.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1276
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9082
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5973
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2116
_reflns_number_gt                1458
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.9628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00053(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2116
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38204(17) 0.28634(18) -0.12129(19) 0.0447(6) Uani 1 1 d . . .
C2 C 0.39150(18) 0.22036(19) -0.2028(2) 0.0523(6) Uani 1 1 d . . .
H2 H 0.3960 0.2463 -0.2676 0.063 Uiso 1 1 calc R . .
C3 C 0.3941(2) 0.1214(2) -0.1886(2) 0.0604(7) Uani 1 1 d . . .
H3 H 0.3997 0.0827 -0.2457 0.073 Uiso 1 1 calc R . .
C4 C 0.38233(18) 0.13153(17) -0.0220(2) 0.0479(6) Uani 1 1 d . . .
C5 C 0.37143(16) 0.21914(16) 0.13815(18) 0.0420(6) Uani 1 1 d . . .
C6 C 0.36850(16) 0.24900(16) 0.24582(17) 0.0400(6) Uani 1 1 d . . .
C7 C 0.36165(17) 0.18019(17) 0.3231(2) 0.0463(6) Uani 1 1 d . . .
H7 H 0.3574 0.1128 0.3060 0.056 Uiso 1 1 calc R . .
C8 C 0.36108(18) 0.21069(17) 0.4240(2) 0.0474(6) Uani 1 1 d . . .
H8 H 0.3563 0.1639 0.4748 0.057 Uiso 1 1 calc R . .
C9 C 0.36764(17) 0.31075(17) 0.45135(19) 0.0442(6) Uani 1 1 d . . .
C10 C 0.37450(18) 0.38058(17) 0.3752(2) 0.0475(6) Uani 1 1 d . . .
H10 H 0.3786 0.4479 0.3924 0.057 Uiso 1 1 calc R . .
C11 C 0.37515(18) 0.34892(17) 0.2745(2) 0.0479(6) Uani 1 1 d . . .
H11 H 0.3802 0.3957 0.2239 0.057 Uiso 1 1 calc R . .
C12 C 0.3756(2) 0.43373(19) 0.5883(2) 0.0662(8) Uani 1 1 d . . .
H12A H 0.4391 0.4601 0.5902 0.099 Uiso 1 1 calc R . .
H12B H 0.3734 0.4381 0.6617 0.099 Uiso 1 1 calc R . .
H12C H 0.3203 0.4713 0.5362 0.099 Uiso 1 1 calc R . .
N1 N 0.38930(17) 0.07238(15) -0.09835(18) 0.0603(6) Uani 1 1 d . . .
N2 N 0.37830(13) 0.23275(13) -0.02779(15) 0.0401(5) Uani 1 1 d . . .
N3 N 0.37149(14) 0.28215(14) 0.06283(15) 0.0427(5) Uani 1 1 d . . .
O1 O 0.37659(14) 0.37608(13) -0.12341(14) 0.0590(5) Uani 1 1 d . . .
O2 O 0.36657(13) 0.33240(12) 0.55381(14) 0.0574(5) Uani 1 1 d . . .
S1 S 0.37725(5) 0.09414(4) 0.10407(5) 0.0559(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0513(16) 0.0430(15) 0.0407(13) 0.0029(11) 0.0187(11) -0.0028(11)
C2 0.0650(17) 0.0548(16) 0.0416(14) -0.0024(12) 0.0254(13) -0.0004(13)
C3 0.082(2) 0.0546(17) 0.0503(16) -0.0126(13) 0.0318(15) 0.0011(14)
C4 0.0575(16) 0.0359(13) 0.0482(15) -0.0018(11) 0.0178(13) -0.0031(11)
C5 0.0458(15) 0.0372(13) 0.0404(13) 0.0025(11) 0.0135(11) -0.0020(10)
C6 0.0429(14) 0.0394(13) 0.0350(12) 0.0020(11) 0.0117(10) -0.0016(10)
C7 0.0558(16) 0.0370(13) 0.0458(14) 0.0008(11) 0.0190(12) -0.0019(11)
C8 0.0608(16) 0.0416(14) 0.0416(14) 0.0080(11) 0.0215(12) -0.0038(11)
C9 0.0498(15) 0.0445(14) 0.0393(13) -0.0010(11) 0.0181(11) -0.0008(11)
C10 0.0617(17) 0.0344(12) 0.0461(14) 0.0005(11) 0.0204(12) -0.0017(11)
C11 0.0629(17) 0.0411(14) 0.0403(14) 0.0047(11) 0.0204(12) -0.0038(12)
C12 0.091(2) 0.0542(17) 0.0576(17) -0.0103(14) 0.0329(16) 0.0057(15)
N1 0.0891(17) 0.0434(12) 0.0498(13) -0.0072(10) 0.0282(12) -0.0006(11)
N2 0.0493(12) 0.0347(10) 0.0369(10) -0.0026(8) 0.0170(9) -0.0001(8)
N3 0.0522(13) 0.0398(11) 0.0364(10) -0.0027(9) 0.0172(9) -0.0020(9)
O1 0.0892(14) 0.0397(10) 0.0539(11) 0.0039(8) 0.0336(10) -0.0010(9)
O2 0.0842(13) 0.0501(11) 0.0454(10) -0.0043(8) 0.0332(10) -0.0022(9)
S1 0.0853(5) 0.0363(4) 0.0479(4) 0.0014(3) 0.0275(4) -0.0035(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.211(3) . ?
C1 C2 1.421(3) . ?
C1 N2 1.423(3) . ?
C2 C3 1.344(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.362(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.299(3) . ?
C4 N2 1.365(3) . ?
C4 S1 1.729(3) . ?
C5 N3 1.290(3) . ?
C5 C6 1.461(3) . ?
C5 S1 1.750(2) . ?
C6 C11 1.390(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 O2 1.359(3) . ?
C9 C10 1.389(3) . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 O2 1.426(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N2 N3 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 129.1(2) . . ?
O1 C1 N2 120.2(2) . . ?
C2 C1 N2 110.7(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 N1 126.1(2) . . ?
C2 C3 H3 117.0 . . ?
N1 C3 H3 117.0 . . ?
N1 C4 N2 125.7(2) . . ?
N1 C4 S1 125.19(19) . . ?
N2 C4 S1 109.06(17) . . ?
N3 C5 C6 122.9(2) . . ?
N3 C5 S1 115.48(17) . . ?
C6 C5 S1 121.64(17) . . ?
C11 C6 C7 118.1(2) . . ?
C11 C6 C5 119.8(2) . . ?
C7 C6 C5 122.2(2) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O2 C9 C8 115.5(2) . . ?
O2 C9 C10 124.8(2) . . ?
C8 C9 C10 119.6(2) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C6 C11 H11 119.0 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 N1 C3 113.2(2) . . ?
C4 N2 N3 116.74(19) . . ?
C4 N2 C1 122.6(2) . . ?
N3 N2 C1 120.67(18) . . ?
C5 N3 N2 109.92(18) . . ?
C9 O2 C12 118.41(19) . . ?
C4 S1 C5 88.78(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.3(3) . . . . ?
N2 C1 C2 C3 1.2(3) . . . . ?
C1 C2 C3 N1 -0.6(4) . . . . ?
N3 C5 C6 C11 -5.9(3) . . . . ?
S1 C5 C6 C11 172.98(17) . . . . ?
N3 C5 C6 C7 175.6(2) . . . . ?
S1 C5 C6 C7 -5.4(3) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 178.7(2) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 O2 -179.9(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
O2 C9 C10 C11 179.8(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C5 C6 C11 C10 -178.9(2) . . . . ?
N2 C4 N1 C3 1.0(4) . . . . ?
S1 C4 N1 C3 -178.69(19) . . . . ?
C2 C3 N1 C4 -0.5(4) . . . . ?
N1 C4 N2 N3 -179.7(2) . . . . ?
S1 C4 N2 N3 0.1(2) . . . . ?
N1 C4 N2 C1 -0.4(4) . . . . ?
S1 C4 N2 C1 179.34(16) . . . . ?
O1 C1 N2 C4 178.8(2) . . . . ?
C2 C1 N2 C4 -0.7(3) . . . . ?
O1 C1 N2 N3 -1.9(3) . . . . ?
C2 C1 N2 N3 178.53(18) . . . . ?
C6 C5 N3 N2 177.83(18) . . . . ?
S1 C5 N3 N2 -1.2(2) . . . . ?
C4 N2 N3 C5 0.7(3) . . . . ?
C1 N2 N3 C5 -178.59(19) . . . . ?
C8 C9 O2 C12 178.5(2) . . . . ?
C10 C9 O2 C12 -1.6(4) . . . . ?
N1 C4 S1 C5 179.2(2) . . . . ?
N2 C4 S1 C5 -0.57(17) . . . . ?
N3 C5 S1 C4 1.04(19) . . . . ?
C6 C5 S1 C4 -177.96(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041


_database_code_depnum_ccdc_archive 'CCDC 779780'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21n
#TrackingRef 'p21n.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 Cl N3 O S'
_chemical_formula_weight         263.70

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.838(4)
_cell_length_b                   4.9244(19)
_cell_length_c                   20.011(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.505(6)
_cell_angle_gamma                90.00
_cell_volume                     1056.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2371
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5348
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2061
_reflns_number_gt                1745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2061
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.91753(16) 1.0176(4) 0.15236(9) 0.0391(4) Uani 1 1 d . . .
C2 C 1.02215(17) 0.9304(4) 0.19495(9) 0.0461(5) Uani 1 1 d . . .
H2 H 1.0385 0.9957 0.2390 0.055 Uiso 1 1 calc R . .
C3 C 1.10134(18) 0.7485(4) 0.17230(11) 0.0493(5) Uani 1 1 d . . .
H3 H 1.1712 0.6883 0.2011 0.059 Uiso 1 1 calc R . .
C4 C 1.07830(18) 0.6536(5) 0.10707(10) 0.0535(5) Uani 1 1 d . . .
H4 H 1.1319 0.5286 0.0917 0.064 Uiso 1 1 calc R . .
C5 C 0.97525(19) 0.7454(4) 0.06483(10) 0.0483(5) Uani 1 1 d . . .
H5 H 0.9609 0.6827 0.0205 0.058 Uiso 1 1 calc R . .
C6 C 0.89174(15) 0.9286(4) 0.08606(8) 0.0357(4) Uani 1 1 d . . .
C7 C 0.78510(15) 1.0098(4) 0.03592(8) 0.0344(4) Uani 1 1 d . . .
C8 C 0.60694(16) 1.2039(4) -0.03510(9) 0.0367(4) Uani 1 1 d . . .
C9 C 0.47030(19) 1.2401(4) -0.12908(10) 0.0500(5) Uani 1 1 d . . .
H9 H 0.4009 1.3250 -0.1531 0.060 Uiso 1 1 calc R . .
C10 C 0.52210(17) 1.0393(4) -0.16020(9) 0.0447(5) Uani 1 1 d . . .
H10 H 0.4883 0.9939 -0.2042 0.054 Uiso 1 1 calc R . .
C11 C 0.62754(16) 0.8928(4) -0.12784(8) 0.0407(4) Uani 1 1 d . . .
Cl1 Cl 0.81942(5) 1.24001(12) 0.18661(3) 0.0615(2) Uani 1 1 d . . .
N1 N 0.76561(13) 0.8835(3) -0.02121(7) 0.0380(3) Uani 1 1 d . . .
N2 N 0.66547(12) 0.9951(3) -0.06152(6) 0.0356(3) Uani 1 1 d . . .
N3 N 0.50985(15) 1.3313(4) -0.06552(8) 0.0486(4) Uani 1 1 d . . .
O1 O 0.68243(13) 0.7074(3) -0.14954(7) 0.0579(4) Uani 1 1 d . . .
S1 S 0.68161(4) 1.27138(9) 0.04545(2) 0.04176(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0401(9) 0.0408(10) 0.0339(9) -0.0015(8) -0.0028(7) 0.0026(8)
C2 0.0463(10) 0.0541(12) 0.0333(9) 0.0004(9) -0.0089(8) 0.0016(9)
C3 0.0401(10) 0.0591(13) 0.0439(11) 0.0080(9) -0.0099(9) 0.0095(9)
C4 0.0449(11) 0.0657(14) 0.0463(11) -0.0016(10) -0.0054(9) 0.0206(10)
C5 0.0480(11) 0.0591(13) 0.0345(10) -0.0057(9) -0.0047(8) 0.0160(9)
C6 0.0350(8) 0.0380(10) 0.0317(8) 0.0008(7) -0.0030(7) 0.0032(7)
C7 0.0362(8) 0.0355(9) 0.0293(8) 0.0004(7) -0.0022(7) 0.0038(7)
C8 0.0402(9) 0.0384(10) 0.0291(9) -0.0005(7) -0.0023(7) 0.0069(7)
C9 0.0491(11) 0.0579(13) 0.0376(11) 0.0016(9) -0.0117(8) 0.0190(9)
C10 0.0462(10) 0.0546(12) 0.0289(9) -0.0031(8) -0.0093(7) 0.0094(9)
C11 0.0418(9) 0.0483(11) 0.0291(8) -0.0041(8) -0.0047(7) 0.0051(8)
Cl1 0.0598(3) 0.0801(4) 0.0388(3) -0.0206(2) -0.0119(2) 0.0252(3)
N1 0.0358(7) 0.0435(9) 0.0313(7) -0.0020(7) -0.0067(6) 0.0107(6)
N2 0.0356(7) 0.0404(8) 0.0277(7) -0.0002(6) -0.0054(6) 0.0085(6)
N3 0.0512(9) 0.0531(10) 0.0364(8) -0.0033(8) -0.0099(7) 0.0200(8)
O1 0.0584(9) 0.0691(10) 0.0407(8) -0.0188(7) -0.0116(7) 0.0261(7)
S1 0.0483(3) 0.0413(3) 0.0313(3) -0.00504(18) -0.0086(2) 0.01484(19)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.386(2) . ?
C1 Cl1 1.7365(19) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.470(2) . ?
C7 N1 1.291(2) . ?
C7 S1 1.7370(17) . ?
C8 N3 1.297(2) . ?
C8 N2 1.356(2) . ?
C8 S1 1.7255(18) . ?
C9 C10 1.336(3) . ?
C9 N3 1.357(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.424(2) . ?
C10 H10 0.9300 . ?
C11 O1 1.205(2) . ?
C11 N2 1.422(2) . ?
N1 N2 1.3681(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.53(17) . . ?
C2 C1 Cl1 116.54(14) . . ?
C6 C1 Cl1 121.92(13) . . ?
C3 C2 C1 119.89(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.28(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.33(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.21(18) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 116.76(16) . . ?
C1 C6 C7 126.48(16) . . ?
C5 C6 C7 116.76(16) . . ?
N1 C7 C6 118.86(15) . . ?
N1 C7 S1 115.52(12) . . ?
C6 C7 S1 125.60(13) . . ?
N3 C8 N2 125.28(16) . . ?
N3 C8 S1 125.55(14) . . ?
N2 C8 S1 109.17(12) . . ?
C10 C9 N3 125.85(17) . . ?
C10 C9 H9 117.1 . . ?
N3 C9 H9 117.1 . . ?
C9 C10 C11 121.84(17) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
O1 C11 N2 120.97(16) . . ?
O1 C11 C10 128.74(17) . . ?
N2 C11 C10 110.29(15) . . ?
C7 N1 N2 109.88(14) . . ?
C8 N2 N1 116.80(13) . . ?
C8 N2 C11 123.03(14) . . ?
N1 N2 C11 120.16(14) . . ?
C8 N3 C9 113.69(16) . . ?
C8 S1 C7 88.62(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(3) . . . . ?
Cl1 C1 C2 C3 177.80(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
Cl1 C1 C6 C5 -178.34(15) . . . . ?
C2 C1 C6 C7 -178.96(17) . . . . ?
Cl1 C1 C6 C7 2.0(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -179.81(19) . . . . ?
C1 C6 C7 N1 -171.48(17) . . . . ?
C5 C6 C7 N1 8.8(3) . . . . ?
C1 C6 C7 S1 10.0(3) . . . . ?
C5 C6 C7 S1 -169.66(15) . . . . ?
N3 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 O1 179.3(2) . . . . ?
C9 C10 C11 N2 -0.7(3) . . . . ?
C6 C7 N1 N2 -177.77(14) . . . . ?
S1 C7 N1 N2 0.86(19) . . . . ?
N3 C8 N2 N1 -179.02(18) . . . . ?
S1 C8 N2 N1 0.63(19) . . . . ?
N3 C8 N2 C11 1.3(3) . . . . ?
S1 C8 N2 C11 -179.04(14) . . . . ?
C7 N1 N2 C8 -1.0(2) . . . . ?
C7 N1 N2 C11 178.71(15) . . . . ?
O1 C11 N2 C8 179.70(18) . . . . ?
C10 C11 N2 C8 -0.3(3) . . . . ?
O1 C11 N2 N1 0.0(3) . . . . ?
C10 C11 N2 N1 -179.94(15) . . . . ?
N2 C8 N3 C9 -1.2(3) . . . . ?
S1 C8 N3 C9 179.25(15) . . . . ?
C10 C9 N3 C8 0.1(3) . . . . ?
N3 C8 S1 C7 179.54(19) . . . . ?
N2 C8 S1 C7 -0.11(13) . . . . ?
N1 C7 S1 C8 -0.45(15) . . . . ?
C6 C7 S1 C8 178.07(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050


_database_code_depnum_ccdc_archive 'CCDC 779674'
