# 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_mo_20120103a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Br N S2'
_chemical_formula_sum            'C14 H10 Br N S2'
_chemical_formula_weight         336.26

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   15.095(3)
_cell_length_b                   5.7769(10)
_cell_length_c                   31.466(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2743.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4575
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.41

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    3.280
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4200
_exptl_absorpt_correction_T_max  0.5458
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11396
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2489
_reflns_number_gt                2174
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0290P)²+28.0982P] 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         2489
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1886
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.14973(10) 0.3636(2) 0.78078(3) 0.1017(5) Uani 1 1 d . . .
S1 S 0.17570(15) -0.1480(3) 1.08155(7) 0.0569(5) Uani 1 1 d . . .
S2 S 0.14935(18) 0.0324(4) 0.99392(6) 0.0637(6) Uani 1 1 d . . .
N1 N 0.0981(4) 0.2460(10) 1.06629(18) 0.0456(14) Uani 1 1 d . . .
C1 C 0.1451(5) 0.0199(12) 1.1244(2) 0.0466(17) Uani 1 1 d . . .
C2 C 0.1544(6) -0.0292(14) 1.1678(2) 0.059(2) Uani 1 1 d . . .
H2 H 0.1813 -0.1648 1.1772 0.070 Uiso 1 1 calc R . .
C3 C 0.1220(7) 0.1318(16) 1.1958(3) 0.071(3) Uani 1 1 d . . .
H3 H 0.1278 0.1052 1.2249 0.085 Uiso 1 1 calc R . .
C4 C 0.0806(6) 0.3347(15) 1.1820(3) 0.062(2) Uani 1 1 d . . .
H4 H 0.0587 0.4387 1.2020 0.074 Uiso 1 1 calc R . .
C5 C 0.0717(5) 0.3832(13) 1.1394(2) 0.0497(18) Uani 1 1 d . . .
H5 H 0.0450 0.5195 1.1302 0.060 Uiso 1 1 calc R . .
C6 C 0.1038(5) 0.2221(12) 1.1108(2) 0.0424(16) Uani 1 1 d . . .
C7 C 0.1328(5) 0.0697(12) 1.0483(2) 0.0445(17) Uani 1 1 d . . .
C8 C 0.0947(6) 0.2878(14) 0.9741(2) 0.060(2) Uani 1 1 d . . .
H8A H 0.0317 0.2791 0.9799 0.072 Uiso 1 1 calc R . .
H8B H 0.1182 0.4242 0.9881 0.072 Uiso 1 1 calc R . .
C9 C 0.1102(5) 0.3040(13) 0.9266(2) 0.0469(17) Uani 1 1 d . . .
C10 C 0.1534(5) 0.4898(13) 0.9095(3) 0.056(2) Uani 1 1 d . . .
H10 H 0.1760 0.6038 0.9273 0.067 Uiso 1 1 calc R . .
C11 C 0.1641(6) 0.5107(15) 0.8654(3) 0.059(2) Uani 1 1 d . . .
H11 H 0.1901 0.6418 0.8536 0.071 Uiso 1 1 calc R . .
C12 C 0.1354(6) 0.3342(15) 0.8403(2) 0.056(2) Uani 1 1 d . . .
C13 C 0.0931(6) 0.1453(14) 0.8563(3) 0.057(2) Uani 1 1 d . . .
H13 H 0.0719 0.0300 0.8383 0.068 Uiso 1 1 calc R . .
C14 C 0.0823(5) 0.1287(13) 0.9000(2) 0.0520(19) Uani 1 1 d . . .
H14 H 0.0558 -0.0025 0.9115 0.062 Uiso 1 1 calc R . .

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
Br1 0.1412(12) 0.1139(10) 0.0499(5) 0.0077(6) 0.0087(6) 0.0255(9)
S1 0.0756(14) 0.0368(10) 0.0583(11) 0.0023(9) -0.0035(10) 0.0098(10)
S2 0.0963(17) 0.0492(12) 0.0457(11) -0.0025(9) 0.0039(11) 0.0159(12)
N1 0.059(4) 0.037(3) 0.040(3) -0.001(3) 0.000(3) 0.002(3)
C1 0.054(4) 0.036(4) 0.049(4) 0.003(3) -0.007(4) 0.003(3)
C2 0.075(6) 0.046(4) 0.055(4) 0.010(4) -0.021(4) 0.004(4)
C3 0.101(7) 0.067(6) 0.044(4) 0.003(4) -0.013(5) 0.002(6)
C4 0.084(6) 0.051(5) 0.051(4) -0.007(4) -0.006(4) -0.001(5)
C5 0.060(5) 0.039(4) 0.049(4) -0.005(3) -0.006(4) 0.001(4)
C6 0.045(4) 0.037(4) 0.046(4) 0.003(3) -0.006(3) -0.006(3)
C7 0.048(4) 0.040(4) 0.045(4) -0.001(3) 0.001(3) -0.001(3)
C8 0.068(6) 0.054(5) 0.058(5) 0.000(4) -0.012(4) 0.010(4)
C9 0.050(4) 0.041(4) 0.050(4) 0.001(3) -0.010(3) 0.002(3)
C10 0.064(5) 0.040(4) 0.064(5) -0.011(4) -0.014(4) -0.004(4)
C11 0.061(5) 0.047(4) 0.070(5) 0.003(4) -0.002(4) -0.003(4)
C12 0.063(5) 0.058(5) 0.048(4) 0.000(4) -0.007(4) 0.009(4)
C13 0.068(5) 0.044(4) 0.058(5) -0.010(4) -0.015(4) 0.004(4)
C14 0.059(5) 0.040(4) 0.056(4) 0.004(3) -0.008(4) -0.007(4)

_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
Br1 C12 1.894(8) . ?
S1 C1 1.724(8) . ?
S1 C7 1.759(7) . ?
S2 C7 1.743(7) . ?
S2 C8 1.802(8) . ?
N1 C7 1.277(9) . ?
N1 C6 1.409(9) . ?
C1 C6 1.392(10) . ?
C1 C2 1.402(10) . ?
C2 C3 1.371(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(10) . ?
C5 H5 0.9300 . ?
C8 C9 1.517(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.366(11) . ?
C9 C14 1.380(10) . ?
C10 C11 1.401(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(12) . ?
C13 C14 1.389(10) . ?
C13 H13 0.9300 . ?
C14 H14 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
C1 S1 C7 88.0(3) . . ?
C7 S2 C8 99.9(4) . . ?
C7 N1 C6 109.7(6) . . ?
C6 C1 C2 121.0(7) . . ?
C6 C1 S1 110.5(5) . . ?
C2 C1 S1 128.4(6) . . ?
C3 C2 C1 117.0(7) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.9(8) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.2(8) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.6(7) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 121.3(7) . . ?
C5 C6 N1 124.1(7) . . ?
C1 C6 N1 114.6(7) . . ?
N1 C7 S2 126.3(6) . . ?
N1 C7 S1 117.2(5) . . ?
S2 C7 S1 116.3(4) . . ?
C9 C8 S2 108.7(6) . . ?
C9 C8 H8A 109.9 . . ?
S2 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
S2 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C14 119.0(7) . . ?
C10 C9 C8 120.7(7) . . ?
C14 C9 C8 120.3(7) . . ?
C9 C10 C11 120.8(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.2(8) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C13 C12 C11 122.5(8) . . ?
C13 C12 Br1 119.3(6) . . ?
C11 C12 Br1 118.0(7) . . ?
C12 C13 C14 118.4(7) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 120.9(7) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 C6 1.3(6) . . . . ?
C7 S1 C1 C2 178.8(8) . . . . ?
C6 C1 C2 C3 -0.8(12) . . . . ?
S1 C1 C2 C3 -178.1(7) . . . . ?
C1 C2 C3 C4 0.8(14) . . . . ?
C2 C3 C4 C5 -1.0(15) . . . . ?
C3 C4 C5 C6 1.1(13) . . . . ?
C4 C5 C6 C1 -1.2(12) . . . . ?
C4 C5 C6 N1 178.9(8) . . . . ?
C2 C1 C6 C5 1.1(12) . . . . ?
S1 C1 C6 C5 178.8(6) . . . . ?
C2 C1 C6 N1 -179.0(7) . . . . ?
S1 C1 C6 N1 -1.3(8) . . . . ?
C7 N1 C6 C5 -179.6(7) . . . . ?
C7 N1 C6 C1 0.5(9) . . . . ?
C6 N1 C7 S2 -174.4(6) . . . . ?
C6 N1 C7 S1 0.6(9) . . . . ?
C8 S2 C7 N1 -5.6(8) . . . . ?
C8 S2 C7 S1 179.4(5) . . . . ?
C1 S1 C7 N1 -1.1(6) . . . . ?
C1 S1 C7 S2 174.3(5) . . . . ?
C7 S2 C8 C9 173.8(6) . . . . ?
S2 C8 C9 C10 -119.2(7) . . . . ?
S2 C8 C9 C14 59.6(9) . . . . ?
C14 C9 C10 C11 4.3(12) . . . . ?
C8 C9 C10 C11 -176.9(8) . . . . ?
C9 C10 C11 C12 -4.2(12) . . . . ?
C10 C11 C12 C13 3.4(13) . . . . ?
C10 C11 C12 Br1 179.8(6) . . . . ?
C11 C12 C13 C14 -2.8(13) . . . . ?
Br1 C12 C13 C14 -179.1(6) . . . . ?
C10 C9 C14 C13 -3.6(12) . . . . ?
C8 C9 C14 C13 177.6(7) . . . . ?
C12 C13 C14 C9 2.8(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.095
_database_code_depnum_ccdc_archive 'CCDC 956820'
#######################################################################
#
#                 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_mo_20120104b_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F N O S2'
_chemical_formula_sum            'C16 H14 F N O S2'
_chemical_formula_weight         319.40

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'
F F 0.0171 0.0103 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.698(3)
_cell_length_b                   8.149(4)
_cell_length_c                   23.607(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.030(8)
_cell_angle_gamma                90.00
_cell_volume                     1480.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4551
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.72

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9202
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6527
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2586
_reflns_number_gt                2016
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1174P)²+9.8150P] 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       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.1140
_refine_ls_wR_factor_ref         0.2753
_refine_ls_wR_factor_gt          0.2717
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
S1 S 0.1874(3) 0.7353(3) 0.26855(8) 0.0460(6) Uani 1 1 d . . .
S2 S 0.0887(3) 0.8871(3) 0.37727(10) 0.0537(7) Uani 1 1 d . . .
F1 F 0.3854(7) 0.1892(7) 0.1844(2) 0.0635(15) Uani 1 1 d . . .
O1 O -0.4243(7) 0.0745(8) 0.4167(3) 0.0541(15) Uani 1 1 d . . .
N1 N 0.1711(7) 0.5669(7) 0.3593(2) 0.0339(13) Uani 1 1 d . . .
C1 C -0.4029(14) -0.0853(12) 0.4398(4) 0.066(3) Uani 1 1 d . . .
H1A H -0.3036 -0.1367 0.4239 0.099 Uiso 1 1 calc R . .
H1B H -0.5049 -0.1494 0.4310 0.099 Uiso 1 1 calc R . .
H1C H -0.3858 -0.0778 0.4802 0.099 Uiso 1 1 calc R . .
C2 C -0.2850(9) 0.1792(10) 0.4204(3) 0.0395(17) Uani 1 1 d . . .
C3 C -0.1435(10) 0.1547(9) 0.4576(3) 0.0409(17) Uani 1 1 d . . .
H3 H -0.1409 0.0657 0.4822 0.049 Uiso 1 1 calc R . .
C4 C -0.0056(9) 0.2653(10) 0.4574(3) 0.0405(17) Uani 1 1 d . . .
H4 H 0.0892 0.2502 0.4824 0.049 Uiso 1 1 calc R . .
C5 C -0.0080(9) 0.3989(9) 0.4201(3) 0.0328(15) Uani 1 1 d . . .
C6 C -0.1508(9) 0.4203(10) 0.3848(3) 0.0394(17) Uani 1 1 d . . .
H6 H -0.1561 0.5101 0.3604 0.047 Uiso 1 1 calc R . .
C7 C -0.2880(9) 0.3098(10) 0.3847(3) 0.0410(17) Uani 1 1 d . . .
H7 H -0.3832 0.3254 0.3599 0.049 Uiso 1 1 calc R . .
C8 C 0.1415(8) 0.5208(9) 0.4192(3) 0.0340(15) Uani 1 1 d . . .
H8 H 0.0987 0.6205 0.4372 0.041 Uiso 1 1 calc R . .
C9 C 0.3074(11) 0.4778(12) 0.4510(3) 0.054(2) Uani 1 1 d . . .
H9A H 0.3003 0.5118 0.4898 0.081 Uiso 1 1 calc R . .
H9B H 0.4029 0.5327 0.4340 0.081 Uiso 1 1 calc R . .
H9C H 0.3252 0.3613 0.4495 0.081 Uiso 1 1 calc R . .
C10 C 0.1494(9) 0.7245(9) 0.3403(3) 0.0377(16) Uani 1 1 d . . .
C11 C 0.2454(9) 0.5286(9) 0.2654(3) 0.0382(17) Uani 1 1 d . . .
C12 C 0.2237(9) 0.4590(9) 0.3179(3) 0.0346(15) Uani 1 1 d . . .
C13 C 0.2550(9) 0.2896(10) 0.3252(3) 0.0409(17) Uani 1 1 d . . .
H13 H 0.2385 0.2382 0.3598 0.049 Uiso 1 1 calc R . .
C14 C 0.3109(10) 0.2030(11) 0.2790(4) 0.049(2) Uani 1 1 d . . .
H14 H 0.3354 0.0916 0.2827 0.059 Uiso 1 1 calc R . .
C15 C 0.3306(10) 0.2779(10) 0.2284(3) 0.0461(19) Uani 1 1 d . . .
C16 C 0.2984(11) 0.4410(11) 0.2188(3) 0.050(2) Uani 1 1 d . . .
H16 H 0.3112 0.4894 0.1835 0.060 Uiso 1 1 calc R . .

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
S1 0.0570(12) 0.0382(11) 0.0432(11) 0.0086(8) 0.0045(8) -0.0005(9)
S2 0.0665(14) 0.0337(11) 0.0611(13) -0.0017(9) 0.0064(10) 0.0075(10)
F1 0.063(3) 0.065(3) 0.063(3) -0.030(3) 0.007(2) -0.009(3)
O1 0.044(3) 0.057(4) 0.062(4) 0.010(3) 0.000(3) -0.012(3)
N1 0.028(3) 0.033(3) 0.041(3) 0.006(2) 0.009(2) 0.003(2)
C1 0.073(6) 0.052(6) 0.073(6) -0.003(5) 0.005(5) -0.020(5)
C2 0.033(3) 0.046(4) 0.040(4) -0.002(3) 0.012(3) 0.000(3)
C3 0.046(4) 0.028(4) 0.048(4) 0.009(3) 0.001(3) 0.001(3)
C4 0.034(3) 0.045(4) 0.042(4) 0.005(3) -0.012(3) 0.006(3)
C5 0.035(3) 0.030(4) 0.033(3) 0.008(3) 0.007(3) 0.005(3)
C6 0.029(3) 0.039(4) 0.049(4) 0.015(3) -0.005(3) 0.005(3)
C7 0.023(3) 0.047(4) 0.053(4) 0.005(4) -0.002(3) -0.003(3)
C8 0.031(3) 0.031(4) 0.040(4) -0.001(3) -0.003(3) 0.007(3)
C9 0.054(5) 0.062(6) 0.045(4) 0.008(4) -0.009(4) -0.019(4)
C10 0.036(3) 0.029(4) 0.048(4) 0.012(3) -0.005(3) -0.008(3)
C11 0.032(3) 0.036(4) 0.047(4) -0.005(3) 0.005(3) -0.015(3)
C12 0.030(3) 0.031(4) 0.043(4) 0.000(3) -0.004(3) -0.004(3)
C13 0.034(4) 0.038(4) 0.050(4) 0.003(3) 0.002(3) -0.001(3)
C14 0.044(4) 0.035(4) 0.069(5) -0.009(4) 0.004(4) 0.003(3)
C15 0.047(4) 0.044(5) 0.047(4) -0.012(4) -0.004(3) -0.022(4)
C16 0.056(5) 0.056(5) 0.037(4) -0.003(4) 0.004(3) -0.020(4)

_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 C10 1.731(8) . ?
S1 C11 1.744(8) . ?
S2 C10 1.663(8) . ?
F1 C15 1.345(9) . ?
O1 C2 1.371(9) . ?
O1 C1 1.419(12) . ?
N1 C10 1.369(9) . ?
N1 C12 1.385(9) . ?
N1 C8 1.488(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.357(11) . ?
C2 C3 1.389(11) . ?
C3 C4 1.393(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(9) . ?
C5 C8 1.521(10) . ?
C6 C7 1.388(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.500(10) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.379(10) . ?
C11 C16 1.385(11) . ?
C12 C13 1.411(11) . ?
C13 C14 1.379(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(13) . ?
C16 H16 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
C10 S1 C11 92.6(4) . . ?
C2 O1 C1 117.9(7) . . ?
C10 N1 C12 113.5(6) . . ?
C10 N1 C8 121.8(6) . . ?
C12 N1 C8 124.6(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 116.9(7) . . ?
C7 C2 C3 120.1(7) . . ?
O1 C2 C3 123.0(7) . . ?
C2 C3 C4 119.1(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.4(7) . . ?
C6 C5 C8 120.0(6) . . ?
C4 C5 C8 121.6(6) . . ?
C5 C6 C7 120.9(7) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 120.8(7) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C9 112.2(6) . . ?
N1 C8 C5 108.7(5) . . ?
C9 C8 C5 118.1(6) . . ?
N1 C8 H8 105.6 . . ?
C9 C8 H8 105.6 . . ?
C5 C8 H8 105.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 S2 127.5(6) . . ?
N1 C10 S1 110.2(6) . . ?
S2 C10 S1 122.3(4) . . ?
C12 C11 C16 123.4(8) . . ?
C12 C11 S1 108.6(5) . . ?
C16 C11 S1 128.0(6) . . ?
C11 C12 N1 114.9(7) . . ?
C11 C12 C13 119.1(7) . . ?
N1 C12 C13 126.0(7) . . ?
C14 C13 C12 117.5(8) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C15 C14 C13 120.9(8) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
F1 C15 C14 119.1(8) . . ?
F1 C15 C16 117.0(8) . . ?
C14 C15 C16 123.9(8) . . ?
C15 C16 C11 115.2(7) . . ?
C15 C16 H16 122.4 . . ?
C11 C16 H16 122.4 . . ?

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
C1 O1 C2 C7 161.1(8) . . . . ?
C1 O1 C2 C3 -17.6(11) . . . . ?
C7 C2 C3 C4 -0.3(11) . . . . ?
O1 C2 C3 C4 178.4(7) . . . . ?
C2 C3 C4 C5 -0.5(11) . . . . ?
C3 C4 C5 C6 1.5(11) . . . . ?
C3 C4 C5 C8 -179.8(7) . . . . ?
C4 C5 C6 C7 -1.8(11) . . . . ?
C8 C5 C6 C7 179.5(7) . . . . ?
O1 C2 C7 C6 -178.7(7) . . . . ?
C3 C2 C7 C6 0.0(11) . . . . ?
C5 C6 C7 C2 1.1(12) . . . . ?
C10 N1 C8 C9 -110.5(8) . . . . ?
C12 N1 C8 C9 68.8(9) . . . . ?
C10 N1 C8 C5 117.0(7) . . . . ?
C12 N1 C8 C5 -63.7(8) . . . . ?
C6 C5 C8 N1 -40.4(8) . . . . ?
C4 C5 C8 N1 141.0(7) . . . . ?
C6 C5 C8 C9 -169.6(7) . . . . ?
C4 C5 C8 C9 11.7(10) . . . . ?
C12 N1 C10 S2 -179.7(5) . . . . ?
C8 N1 C10 S2 -0.2(10) . . . . ?
C12 N1 C10 S1 2.4(7) . . . . ?
C8 N1 C10 S1 -178.1(5) . . . . ?
C11 S1 C10 N1 -3.4(5) . . . . ?
C11 S1 C10 S2 178.6(5) . . . . ?
C10 S1 C11 C12 3.4(5) . . . . ?
C10 S1 C11 C16 -179.0(7) . . . . ?
C16 C11 C12 N1 179.6(7) . . . . ?
S1 C11 C12 N1 -2.7(8) . . . . ?
C16 C11 C12 C13 -0.6(11) . . . . ?
S1 C11 C12 C13 177.1(5) . . . . ?
C10 N1 C12 C11 0.2(9) . . . . ?
C8 N1 C12 C11 -179.2(6) . . . . ?
C10 N1 C12 C13 -179.5(7) . . . . ?
C8 N1 C12 C13 1.0(11) . . . . ?
C11 C12 C13 C14 1.8(10) . . . . ?
N1 C12 C13 C14 -178.5(7) . . . . ?
C12 C13 C14 C15 -1.6(11) . . . . ?
C13 C14 C15 F1 180.0(7) . . . . ?
C13 C14 C15 C16 0.2(13) . . . . ?
F1 C15 C16 C11 -178.8(6) . . . . ?
C14 C15 C16 C11 0.9(12) . . . . ?
C12 C11 C16 C15 -0.7(11) . . . . ?
S1 C11 C16 C15 -178.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 956821'
