# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_fs328_0m
_database_code_depnum_ccdc_archive 'CCDC 1011197'
_audit_update_record             
;
2014-06-30 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2 O2 S'
_chemical_formula_sum            'C12 H8 N2 O2 S'
_chemical_formula_weight         244.26

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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/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                   4.8213(4)
_cell_length_b                   14.2939(12)
_cell_length_c                   15.8175(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8920(18)
_cell_angle_gamma                90.00
_cell_volume                     1087.55(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294
_cell_measurement_reflns_used    3862
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.94
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.241
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_max          0.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8466
_exptl_absorpt_correction_T_max  0.9341
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      294
_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 SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6188
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.01
_reflns_number_total             2114
_reflns_number_gt                1889
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0727P)²+0.3030P] 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         2114
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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
S1 S 0.28352(10) 0.73912(3) 0.46534(3) 0.04390(19) Uani 1 1 d . . .
O1 O 0.6695(3) 0.71224(9) 0.21228(8) 0.0503(4) Uani 1 1 d . . .
O2 O 0.9904(3) 0.80508(9) 0.16925(7) 0.0427(3) Uani 1 1 d . . .
N1 N 0.5589(3) 0.88681(9) 0.42897(8) 0.0361(3) Uani 1 1 d . . .
N2 N 0.3273(5) 0.89941(12) 0.55459(11) 0.0620(5) Uani 1 1 d . . .
H2A H 0.3823 0.9560 0.5634 0.074 Uiso 1 1 calc R . .
H2B H 0.2240 0.8726 0.5896 0.074 Uiso 1 1 calc R . .
C1 C 0.8021(4) 0.78271(12) 0.22719(10) 0.0357(4) Uani 1 1 d . . .
C2 C 1.1485(3) 0.88506(12) 0.17416(10) 0.0368(4) Uani 1 1 d . . .
C3 C 1.3274(4) 0.90034(16) 0.11093(11) 0.0479(5) Uani 1 1 d . . .
H3A H 1.3388 0.8578 0.0668 0.057 Uiso 1 1 calc R . .
C4 C 1.4886(4) 0.98010(16) 0.11473(12) 0.0515(5) Uani 1 1 d . . .
H4A H 1.6106 0.9914 0.0728 0.062 Uiso 1 1 calc R . .
C5 C 1.4712(4) 1.04343(15) 0.18007(13) 0.0480(5) Uani 1 1 d . . .
H5A H 1.5804 1.0971 0.1815 0.058 Uiso 1 1 calc R . .
C6 C 1.2937(4) 1.02775(13) 0.24298(12) 0.0421(4) Uani 1 1 d . . .
H6A H 1.2830 1.0709 0.2867 0.051 Uiso 1 1 calc R . .
C7 C 1.1285(3) 0.94686(12) 0.24143(10) 0.0332(4) Uani 1 1 d . . .
C8 C 0.9431(3) 0.92302(11) 0.30510(10) 0.0333(4) Uani 1 1 d . . .
H8A H 0.9320 0.9624 0.3515 0.040 Uiso 1 1 calc R . .
C9 C 0.7838(3) 0.84528(11) 0.29996(9) 0.0307(3) Uani 1 1 d . . .
C10 C 0.5952(3) 0.82101(11) 0.36585(9) 0.0305(3) Uani 1 1 d . . .
C11 C 0.4611(4) 0.73875(12) 0.37497(11) 0.0370(4) Uani 1 1 d . . .
H11A H 0.4647 0.6888 0.3373 0.044 Uiso 1 1 calc R . .
C12 C 0.4030(4) 0.85267(12) 0.48586(10) 0.0389(4) Uani 1 1 d . . .


_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
S1 C11 1.7153(18) . ?
S1 C12 1.7453(18) . ?
O1 C1 1.208(2) . ?
O2 C1 1.371(2) . ?
O2 C2 1.373(2) . ?
N1 C12 1.305(2) . ?
N1 C10 1.391(2) . ?
N2 C12 1.347(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C9 1.465(2) . ?
C2 C3 1.382(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.403(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.433(2) . ?
C8 C9 1.350(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.470(2) . ?
C10 C11 1.355(2) . ?
C11 H11A 0.9300 . ?

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
C11 S1 C12 88.90(8) . . ?
C1 O2 C2 123.13(13) . . ?
C12 N1 C10 110.39(14) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O1 C1 O2 115.46(14) . . ?
O1 C1 C9 127.09(15) . . ?
O2 C1 C9 117.44(15) . . ?
O2 C2 C3 117.52(16) . . ?
O2 C2 C7 120.33(14) . . ?
C3 C2 C7 122.14(17) . . ?
C4 C3 C2 118.49(18) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 120.79(17) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 120.51(19) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 120.15(18) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C2 C7 C6 117.91(15) . . ?
C2 C7 C8 117.73(15) . . ?
C6 C7 C8 124.35(16) . . ?
C9 C8 C7 122.21(15) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C1 119.05(14) . . ?
C8 C9 C10 121.87(14) . . ?
C1 C9 C10 119.08(14) . . ?
C11 C10 N1 115.22(14) . . ?
C11 C10 C9 127.09(14) . . ?
N1 C10 C9 117.59(14) . . ?
C10 C11 S1 110.79(12) . . ?
C10 C11 H11A 124.6 . . ?
S1 C11 H11A 124.6 . . ?
N1 C12 N2 124.82(16) . . ?
N1 C12 S1 114.69(12) . . ?
N2 C12 S1 120.47(14) . . ?

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
C2 O2 C1 O1 176.72(15) . . . . ?
C2 O2 C1 C9 -3.7(2) . . . . ?
C1 O2 C2 C3 -178.92(15) . . . . ?
C1 O2 C2 C7 1.9(2) . . . . ?
O2 C2 C3 C4 -179.84(15) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
O2 C2 C7 C6 -179.63(14) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
O2 C2 C7 C8 1.1(2) . . . . ?
C3 C2 C7 C8 -178.03(15) . . . . ?
C5 C6 C7 C2 -0.9(2) . . . . ?
C5 C6 C7 C8 178.25(15) . . . . ?
C2 C7 C8 C9 -2.2(2) . . . . ?
C6 C7 C8 C9 178.58(15) . . . . ?
C7 C8 C9 C1 0.4(2) . . . . ?
C7 C8 C9 C10 179.62(14) . . . . ?
O1 C1 C9 C8 -177.97(17) . . . . ?
O2 C1 C9 C8 2.5(2) . . . . ?
O1 C1 C9 C10 2.8(3) . . . . ?
O2 C1 C9 C10 -176.76(13) . . . . ?
C12 N1 C10 C11 1.4(2) . . . . ?
C12 N1 C10 C9 -175.32(14) . . . . ?
C8 C9 C10 C11 -168.38(16) . . . . ?
C1 C9 C10 C11 10.8(2) . . . . ?
C8 C9 C10 N1 7.9(2) . . . . ?
C1 C9 C10 N1 -172.87(14) . . . . ?
N1 C10 C11 S1 -0.84(19) . . . . ?
C9 C10 C11 S1 175.54(13) . . . . ?
C12 S1 C11 C10 0.05(14) . . . . ?
C10 N1 C12 N2 -179.35(19) . . . . ?
C10 N1 C12 S1 -1.36(19) . . . . ?
C11 S1 C12 N1 0.79(15) . . . . ?
C11 S1 C12 N2 178.87(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.050



