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

####################################################################### 
# 
# 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/. 
# 
# 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_complex_4
_database_code_depnum_ccdc_archive 'CCDC 1027456'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_THETM01_complex_4           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This was the best of several crystals examined but was still 
poorly diffracting to high angle, so data beyond 2theta = 45' 
were omitted.
;
_vrf_PLAT023_complex_4           
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      22.49 Degree
RESPONSE: There was a shortage of high angle data due to poor crystal 
quality. However overall data:parameter ratio > 9 and clearly reveals 
molecular structure and connectivity, albeit with slightly low bond 
precision (see ALERT C errors below).
;


# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H32 Cu2 N12 O4 S4, 2(C H4 O) '
_chemical_formula_sum            'C50 H40 Cu2 N12 O6 S4'
_chemical_formula_weight         1160.26

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9974(18)
_cell_length_b                   10.434(2)
_cell_length_c                   14.204(3)
_cell_angle_alpha                75.65(3)
_cell_angle_beta                 88.65(3)
_cell_angle_gamma                68.44(3)
_cell_volume                     1198.1(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9580
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rods
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.836

_exptl_absorpt_correction_T_max  0.941

_exptl_absorpt_process_details   
;

multi-scan from symmetry-related measurements
 
 Sortav (Blessing 1995)

;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'

_diffrn_reflns_number            11353
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         22.49
_reflns_number_total             3124
_reflns_number_gt                2621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_molecular_graphics    'Mercury v.3.0 (CCD), XP'
_computing_publication_material  'Bruker SHELXTL XCIF'


_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)+(0.0536P)²+1.6368P] 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         3124
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.003
_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
O3 O 0.8733(8) 0.2981(8) 0.7447(5) 0.140(2) Uani 1 1 d . . .
H26 H 0.8874 0.2142 0.7441 0.209 Uiso 1 1 calc R . .
Cu1 Cu 0.48668(6) 0.04227(6) 0.27704(3) 0.0342(2) Uani 1 1 d . . .
S2 S 0.10861(13) 0.12402(13) 0.22716(8) 0.0389(3) Uani 1 1 d . . .
N1 N 0.5747(4) 0.0849(4) 0.1498(2) 0.0323(8) Uani 1 1 d . . .
N4 N 0.4004(4) -0.0139(4) 0.4031(2) 0.0310(8) Uani 1 1 d . . .
N3 N 0.6111(4) -0.1783(4) 0.3082(2) 0.0344(9) Uani 1 1 d . . .
O1 O 0.1043(4) -0.0114(3) 0.2109(2) 0.0484(8) Uani 1 1 d . . .
N2 N 0.2788(4) 0.1409(4) 0.1910(2) 0.0352(9) Uani 1 1 d . . .
C5 C 0.4683(5) 0.1442(4) 0.0713(3) 0.0312(10) Uani 1 1 d . . .
C17 C 0.5605(5) -0.2462(5) 0.3869(3) 0.0345(10) Uani 1 1 d . . .
C18 C 0.4393(5) -0.1527(5) 0.4403(3) 0.0337(10) Uani 1 1 d . . .
C6 C 0.2989(5) 0.1751(4) 0.0931(3) 0.0326(10) Uani 1 1 d . . .
C1 C 0.7306(5) 0.0565(5) 0.1365(3) 0.0392(11) Uani 1 1 d . . .
H1 H 0.8052 0.0189 0.1919 0.047 Uiso 1 1 calc R . .
C13 C 0.7186(5) -0.2570(5) 0.2569(3) 0.0411(11) Uani 1 1 d . . .
H13 H 0.7571 -0.2097 0.2015 0.049 Uiso 1 1 calc R . .
C8 C -0.0226(5) 0.2623(5) 0.1325(3) 0.0375(11) Uani 1 1 d . . .
C7 C 0.0322(5) 0.2912(5) 0.0397(3) 0.0374(11) Uani 1 1 d . . .
C16 C 0.6158(6) -0.3932(5) 0.4179(3) 0.0455(12) Uani 1 1 d . . .
H16 H 0.5814 -0.4391 0.4758 0.055 Uiso 1 1 calc R . .
C3 C 0.6787(6) 0.1390(5) -0.0348(4) 0.0484(13) Uani 1 1 d . . .
H3 H 0.7150 0.1556 -0.0984 0.058 Uiso 1 1 calc R . .
C2 C 0.7857(6) 0.0799(5) 0.0456(4) 0.0446(12) Uani 1 1 d . . .
H2 H 0.8972 0.0554 0.0383 0.053 Uiso 1 1 calc R . .
C4 C 0.5177(6) 0.1738(5) -0.0221(3) 0.0418(12) Uani 1 1 d . . .
H4 H 0.4413 0.2177 -0.0767 0.050 Uiso 1 1 calc R . .
C15 C 0.7225(6) -0.4720(5) 0.3627(4) 0.0494(13) Uani 1 1 d . . .
H15 H 0.7591 -0.5732 0.3808 0.059 Uiso 1 1 calc R . .
C9 C -0.1811(5) 0.3301(5) 0.1509(4) 0.0439(12) Uani 1 1 d . . .
H9 H -0.2154 0.3094 0.2147 0.053 Uiso 1 1 calc R . .
C10 C -0.2879(6) 0.4280(5) 0.0751(4) 0.0514(13) Uani 1 1 d . . .
H10 H -0.3961 0.4763 0.0867 0.062 Uiso 1 1 calc R . .
C14 C 0.7743(6) -0.4036(5) 0.2825(4) 0.0482(13) Uani 1 1 d . . .
H14 H 0.8483 -0.4564 0.2443 0.058 Uiso 1 1 calc R . .
C12 C -0.0804(6) 0.3876(5) -0.0365(4) 0.0487(13) Uani 1 1 d . . .
H12 H -0.0483 0.4059 -0.1010 0.058 Uiso 1 1 calc R . .
C11 C -0.2367(6) 0.4555(6) -0.0182(4) 0.0573(14) Uani 1 1 d . . .
H11 H -0.3109 0.5224 -0.0701 0.069 Uiso 1 1 calc R . .
S1 S 0.27765(14) -0.14393(13) 0.59363(8) 0.0400(3) Uani 1 1 d . . .
N5 N 0.1920(4) 0.2373(4) 0.0197(2) 0.0372(9) Uani 1 1 d . . .
N6 N 0.3868(5) -0.2234(4) 0.5155(3) 0.0415(9) Uani 1 1 d . . .
C20 C 0.2843(5) 0.0815(5) 0.4465(3) 0.0335(10) Uani 1 1 d . . .
C19 C 0.2095(5) 0.0367(5) 0.5273(3) 0.0375(11) Uani 1 1 d . . .
O2 O 0.3885(4) -0.1576(3) 0.6760(2) 0.0423(8) Uani 1 1 d . . .
C24 C 0.2386(5) 0.2283(5) 0.4056(3) 0.0388(11) Uani 1 1 d . . .
H24 H 0.2906 0.2620 0.3515 0.047 Uiso 1 1 calc R . .
C23 C 0.1187(6) 0.3239(6) 0.4434(3) 0.0487(13) Uani 1 1 d . . .
H23 H 0.0888 0.4233 0.4154 0.058 Uiso 1 1 calc R . .
C21 C 0.0850(5) 0.1350(5) 0.5645(3) 0.0444(12) Uani 1 1 d . . .
H21 H 0.0324 0.1027 0.6187 0.053 Uiso 1 1 calc R . .
C22 C 0.0412(6) 0.2764(6) 0.5219(4) 0.0524(14) Uani 1 1 d . . .
H22 H -0.0433 0.3434 0.5461 0.063 Uiso 1 1 calc R . .
C25 C 0.7157(10) 0.3852(11) 0.7156(7) 0.155(5) Uani 1 1 d . . .
H25A H 0.6483 0.3707 0.7692 0.232 Uiso 1 1 calc R . .
H25B H 0.6809 0.3618 0.6593 0.232 Uiso 1 1 calc R . .
H25C H 0.7060 0.4851 0.6974 0.232 Uiso 1 1 calc R . .


_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
O3 C25 1.379(9) . ?
Cu1 N1 1.971(3) . ?
Cu1 N4 1.975(3) . ?
Cu1 N2 2.030(3) . ?
Cu1 N3 2.091(4) . ?
Cu1 O2 2.140(3) 2_656 ?
S2 O1 1.501(3) . ?
S2 N2 1.660(4) . ?
S2 C8 1.773(4) . ?
N1 C1 1.342(5) . ?
N1 C5 1.346(5) . ?
N4 C18 1.325(5) . ?
N4 C20 1.404(5) . ?
N3 C17 1.333(6) . ?
N3 C13 1.349(5) . ?
N2 C6 1.372(5) . ?
C5 C4 1.387(6) . ?
C5 C6 1.480(6) . ?
C17 C16 1.382(6) . ?
C17 C18 1.505(6) . ?
C18 N6 1.323(6) . ?
C6 N5 1.298(5) . ?
C1 C2 1.369(6) . ?
C13 C14 1.376(7) . ?
C8 C9 1.391(6) . ?
C8 C7 1.398(6) . ?
C7 N5 1.389(6) . ?
C7 C12 1.404(6) . ?
C16 C15 1.385(7) . ?
C3 C2 1.371(7) . ?
C3 C4 1.377(7) . ?
C15 C14 1.357(7) . ?
C9 C10 1.382(7) . ?
C10 C11 1.389(7) . ?
C12 C11 1.375(7) . ?
S1 O2 1.501(3) . ?
S1 N6 1.640(4) . ?
S1 C19 1.765(5) . ?
C20 C19 1.385(6) . ?
C20 C24 1.400(6) . ?
C19 C21 1.407(6) . ?
O2 Cu1 2.140(3) 2_656 ?
C24 C23 1.376(6) . ?
C23 C22 1.385(7) . ?
C21 C22 1.356(7) . ?
C1 H1 0.950 . ?
C2 H2 0.950 . ?
C3 H3 0.950 . ?
C4 H4 0.949 . ?
C9 H9 0.950 . ?
C10 H10 0.950 . ?
C11 H11 0.950 . ?
C12 H12 0.949 . ?
C13 H13 0.950 . ?
C14 H14 0.950 . ?
C15 H15 0.950 . ?
C16 H16 0.950 . ?
C21 H21 0.950 . ?
C22 H22 0.949 . ?
C23 H23 0.950 . ?
C24 H24 0.950 . ?
C25 H25A 0.979 . ?
C25 H25B 0.981 . ?
C25 H25C 0.981 . ?
O3 H26 0.839 . ?
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
N1 Cu1 N4 175.90(14) . . ?
N1 Cu1 N2 80.80(13) . . ?
N4 Cu1 N2 99.36(14) . . ?
N1 Cu1 N3 95.35(14) . . ?
N4 Cu1 N3 81.06(14) . . ?
N2 Cu1 N3 121.88(14) . . ?
N1 Cu1 O2 86.58(13) . 2_656 ?
N4 Cu1 O2 96.73(13) . 2_656 ?
N2 Cu1 O2 122.52(13) . 2_656 ?
N3 Cu1 O2 114.98(13) . 2_656 ?
O1 S2 N2 109.35(19) . . ?
O1 S2 C8 105.11(19) . . ?
N2 S2 C8 97.9(2) . . ?
C1 N1 C5 118.9(4) . . ?
C1 N1 Cu1 124.9(3) . . ?
C5 N1 Cu1 116.2(3) . . ?
C18 N4 C20 118.8(4) . . ?
C18 N4 Cu1 116.0(3) . . ?
C20 N4 Cu1 124.5(3) . . ?
C17 N3 C13 118.3(4) . . ?
C17 N3 Cu1 111.5(3) . . ?
C13 N3 Cu1 129.9(3) . . ?
C6 N2 S2 119.1(3) . . ?
C6 N2 Cu1 114.3(3) . . ?
S2 N2 Cu1 122.36(19) . . ?
N1 C5 C4 121.1(4) . . ?
N1 C5 C6 115.1(3) . . ?
C4 C5 C6 123.7(4) . . ?
N3 C17 C16 122.4(4) . . ?
N3 C17 C18 115.8(4) . . ?
C16 C17 C18 121.8(4) . . ?
N6 C18 N4 130.9(4) . . ?
N6 C18 C17 114.2(4) . . ?
N4 C18 C17 114.9(4) . . ?
N5 C6 N2 129.6(4) . . ?
N5 C6 C5 117.0(4) . . ?
N2 C6 C5 113.2(3) . . ?
N1 C1 C2 122.1(4) . . ?
N3 C13 C14 122.0(4) . . ?
C9 C8 C7 121.9(4) . . ?
C9 C8 S2 118.8(4) . . ?
C7 C8 S2 119.1(3) . . ?
N5 C7 C8 124.0(4) . . ?
N5 C7 C12 118.2(4) . . ?
C8 C7 C12 117.6(4) . . ?
C17 C16 C15 118.4(5) . . ?
C2 C3 C4 119.0(4) . . ?
C1 C2 C3 119.5(4) . . ?
C3 C4 C5 119.3(4) . . ?
C14 C15 C16 119.5(5) . . ?
C10 C9 C8 119.1(5) . . ?
C9 C10 C11 119.8(5) . . ?
C15 C14 C13 119.4(4) . . ?
C11 C12 C7 120.4(5) . . ?
C12 C11 C10 121.0(5) . . ?
O2 S1 N6 107.89(19) . . ?
O2 S1 C19 105.76(19) . . ?
N6 S1 C19 101.6(2) . . ?
C6 N5 C7 117.7(4) . . ?
C18 N6 S1 121.7(3) . . ?
C19 C20 C24 118.1(4) . . ?
C19 C20 N4 122.8(4) . . ?
C24 C20 N4 119.1(4) . . ?
C20 C19 C21 121.3(4) . . ?
C20 C19 S1 121.2(3) . . ?
C21 C19 S1 117.3(3) . . ?
S1 O2 Cu1 140.65(19) . 2_656 ?
C23 C24 C20 120.3(4) . . ?
C24 C23 C22 120.6(5) . . ?
C22 C21 C19 119.1(4) . . ?
C21 C22 C23 120.6(4) . . ?
N1 C1 H1 119 . . ?
C2 C1 H1 119 . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
C2 C3 H3 121 . . ?
C4 C3 H3 120 . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C8 C9 H9 120 . . ?
C10 c9 H9 120 . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C10 C11 H11 119 . . ?
C12 C11 H11 120 . . ?
C7 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
N3 C13 H13 119 . . ?
C14 C13 H13 119 . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C15 C16 H16 121 . . ?
C17 C16 H16 121 . . ?
C19 C21 H21 120 . . ?
C22 C21 H21 120 . . ?
C21 C22 H22 120 . . ?
C23 C22 H22 120 . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C20 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
C25 O3 H26 110 . . ?
O3 C25 H25A 110 . . ?
O3 C25 H25B 109 . . ?
O3 C25 H25C 109 . . ?
H25A C25 H25B 109 . . ?
H25A C25 H25C 109 . . ?
H25B C25 H25C 109 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        22.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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/. 
# 
# 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_compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1027457'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N2 O S'
_chemical_formula_sum            'C13 H10 N2 O S'
_chemical_formula_weight         242.29

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.4577(5)
_cell_length_b                   11.9926(7)
_cell_length_c                   21.3438(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2164.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.073
_cell_measurement_theta_max      33.244

_exptl_crystal_description       lathe
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8841
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
APEX-II, Bruker AXS, Madison, WI, USA.  
;

_diffrn_ambient_temperature      150(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10187
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1904
_reflns_number_gt                1809
_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    'Mercury v.3.0 (CCD)'
_computing_publication_material  'Bruker SHELXTL XCIF'

_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. 
 Structure solved by direct methods to reveal all non-H atoms. All H atoms
 located in subsequent difference map and refined freely with common U(iso)'
;

_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)+(0.0461P)²+2.5867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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 0.04937(7) 0.81249(5) 0.09887(3) 0.0162(2) Uani 1 1 d . . .
O1 O 0.1908(2) 0.75984(13) 0.12965(8) 0.0213(4) Uani 1 1 d . . .
N1 N 0.1153(2) 0.88479(15) 0.03786(9) 0.0162(4) Uani 1 1 d . . .
N2 N 0.1561(2) 1.05204(16) 0.09415(9) 0.0153(4) Uani 1 1 d . . .
C11 C -0.0094(3) 0.92110(19) 0.15005(11) 0.0162(5) Uani 1 1 d . . .
C12 C -0.1148(3) 0.8967(2) 0.19827(12) 0.0233(6) Uani 1 1 d . . .
C13 C -0.1544(3) 0.9784(2) 0.24112(12) 0.0260(6) Uani 1 1 d . . .
C14 C -0.0905(3) 1.0848(2) 0.23517(11) 0.0245(6) Uani 1 1 d . . .
C15 C 0.0128(3) 1.1101(2) 0.18714(11) 0.0193(5) Uani 1 1 d . . .
C16 C 0.0535(3) 1.02784(19) 0.14366(10) 0.0156(5) Uani 1 1 d . . .
C20 C 0.1754(3) 0.98497(18) 0.04392(10) 0.0144(5) Uani 1 1 d . . .
C21 C 0.2705(3) 1.02810(18) -0.00938(10) 0.0139(5) Uani 1 1 d . . .
C22 C 0.3362(3) 0.95137(19) -0.05120(11) 0.0173(5) Uani 1 1 d . . .
C23 C 0.4282(3) 0.9882(2) -0.10034(11) 0.0206(5) Uani 1 1 d . . .
C24 C 0.4585(3) 1.1011(2) -0.10830(12) 0.0225(6) Uani 1 1 d . . .
C25 C 0.3925(3) 1.1772(2) -0.06718(11) 0.0207(5) Uani 1 1 d . . .
C26 C 0.2967(3) 1.14147(19) -0.01847(11) 0.0166(5) Uani 1 1 d . . .
H15 H 0.055(3) 1.182(2) 0.1833(13) 0.022(2) Uiso 1 1 d . . .
H12 H -0.160(3) 0.822(2) 0.2030(12) 0.022(2) Uiso 1 1 d . . .
H2 H 0.208(3) 1.114(2) 0.0956(12) 0.022(2) Uiso 1 1 d . . .
H13 H -0.224(3) 0.959(2) 0.2728(12) 0.022(2) Uiso 1 1 d . . .
H14 H -0.118(3) 1.141(2) 0.2652(12) 0.022(2) Uiso 1 1 d . . .
H23 H 0.471(3) 0.939(2) -0.1259(13) 0.022(2) Uiso 1 1 d . . .
H22 H 0.317(3) 0.873(2) -0.0446(12) 0.022(2) Uiso 1 1 d . . .
H25 H 0.412(3) 1.256(2) -0.0718(12) 0.022(2) Uiso 1 1 d . . .
H26 H 0.250(3) 1.196(2) 0.0089(12) 0.022(2) Uiso 1 1 d . . .
H24 H 0.524(3) 1.126(2) -0.1429(13) 0.022(2) Uiso 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 O1 1.5036(17) . ?
S1 N1 1.6610(19) . ?
S1 C11 1.771(2) . ?
N1 C20 1.311(3) . ?
N2 C20 1.350(3) . ?
N2 C16 1.398(3) . ?
N2 H2 0.86(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.382(4) . ?
C12 H12 0.98(3) . ?
C13 C14 1.391(4) . ?
C13 H13 0.93(3) . ?
C14 C15 1.381(4) . ?
C14 H14 0.96(3) . ?
C15 C16 1.397(3) . ?
C15 H15 0.94(3) . ?
C20 C21 1.486(3) . ?
C21 C26 1.391(3) . ?
C21 C22 1.397(3) . ?
C22 C23 1.379(3) . ?
C22 H22 0.96(3) . ?
C23 C24 1.389(4) . ?
C23 H23 0.88(3) . ?
C24 C25 1.384(4) . ?
C24 H24 0.97(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.96(3) . ?
C26 H26 0.96(3) . ?

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 S1 N1 107.13(10) . . ?
O1 S1 C11 105.22(10) . . ?
N1 S1 C11 101.17(10) . . ?
C20 N1 S1 122.10(16) . . ?
C20 N2 C16 123.5(2) . . ?
C20 N2 H2 118.7(18) . . ?
C16 N2 H2 117.8(18) . . ?
C12 C11 C16 120.6(2) . . ?
C12 C11 S1 118.74(18) . . ?
C16 C11 S1 120.58(18) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 119.0(16) . . ?
C11 C12 H12 121.4(16) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 117.3(16) . . ?
C14 C13 H13 123.0(16) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.4(16) . . ?
C13 C14 H14 119.6(16) . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.4(17) . . ?
C16 C15 H15 120.0(17) . . ?
C11 C16 C15 119.3(2) . . ?
C11 C16 N2 120.1(2) . . ?
C15 C16 N2 120.6(2) . . ?
N1 C20 N2 125.2(2) . . ?
N1 C20 C21 117.0(2) . . ?
N2 C20 C21 117.78(19) . . ?
C26 C21 C22 119.4(2) . . ?
C26 C21 C20 122.2(2) . . ?
C22 C21 C20 118.35(19) . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 H22 121.1(16) . . ?
C21 C22 H22 118.9(16) . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.0(18) . . ?
C24 C23 H23 120.3(18) . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.9(16) . . ?
C23 C24 H24 119.7(16) . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 120.9(16) . . ?
C26 C25 H25 118.7(16) . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 119.1(16) . . ?
C21 C26 H26 120.9(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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/. 
# 
# 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_compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1027458'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 N2 O S2'
_chemical_formula_sum            'C11 H8 N2 O S2'
_chemical_formula_weight         248.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   8.2057(5)
_cell_length_b                   18.0582(12)
_cell_length_c                   7.4221(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.185(3)
_cell_angle_gamma                90
_cell_volume                     1025.48(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8892
_cell_measurement_theta_min      2.662
_cell_measurement_theta_max      30.620

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.494
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8230
_exptl_absorpt_correction_T_max  0.9163
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
APEX-II, Bruker AXS, Madison, WI, USA
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II with CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8216
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.662
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             1808
_reflns_number_gt                1726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2013 (Sheldrick, 2013)'
_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. 
 Structure solved by direct methods to reveal all non-H atoms. H atoms added
 at calculated positions except N-H which was located in difference map and 
 refined with constrained N-H distance and riding thermal parameter.
 All non-H atoms refined anisotropically. 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+1.7815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1808
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.159
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26614(8) 0.63587(3) 0.89610(9) 0.02138(19) Uani 1 1 d . . . . .
O1 O 0.3842(2) 0.62865(10) 0.7816(3) 0.0244(4) Uani 1 1 d . . . . .
N1 N 0.1490(3) 0.55856(12) 0.8642(3) 0.0213(5) Uani 1 1 d . . . . .
S2 S -0.04643(9) 0.43009(4) 0.66426(10) 0.0283(2) Uani 1 1 d . . . . .
N2 N 0.3735(3) 0.49230(11) 1.1039(3) 0.0167(4) Uani 1 1 d D . . . .
H2 H 0.421(3) 0.4475(11) 1.142(4) 0.020 Uiso 1 1 d D U . . .
C11 C 0.4088(3) 0.62500(14) 1.1386(4) 0.0205(5) Uani 1 1 d . . . . .
C12 C 0.4841(4) 0.68660(15) 1.2515(4) 0.0262(6) Uani 1 1 d . . . . .
H12 H 0.4451 0.7351 1.2067 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6157(4) 0.67642(16) 1.4291(4) 0.0295(6) Uani 1 1 d . . . . .
H13 H 0.6648 0.7180 1.5087 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6768(4) 0.60553(16) 1.4918(4) 0.0264(6) Uani 1 1 d . . . . .
H14 H 0.7726 0.5993 1.6100 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5992(3) 0.54428(15) 1.3836(4) 0.0207(6) Uani 1 1 d . . . . .
H15 H 0.6397 0.4960 1.4283 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4605(3) 0.55384(14) 1.2077(4) 0.0179(5) Uani 1 1 d . . . . .
C20 C 0.2214(3) 0.49681(14) 0.9512(3) 0.0181(5) Uani 1 1 d . . . . .
C21 C 0.1277(3) 0.42807(14) 0.8791(3) 0.0181(5) Uani 1 1 d . . . . .
C22 C 0.1557(3) 0.35629(13) 0.9628(4) 0.0185(5) Uani 1 1 d . . . . .
H22 H 0.2440 0.3436 1.0827 0.022 Uiso 1 1 calc R U . . .
C23 C 0.0309(4) 0.30613(15) 0.8392(4) 0.0278(6) Uani 1 1 d . . . . .
H23 H 0.0281 0.2549 0.8673 0.033 Uiso 1 1 calc R U . . .
C24 C -0.0842(4) 0.33836(16) 0.6770(4) 0.0283(6) Uani 1 1 d . . . . .
H24 H -0.1755 0.3122 0.5815 0.034 Uiso 1 1 calc R U . . .


_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 O1 1.5080(19) . ?
S1 N1 1.663(2) . ?
S1 C11 1.768(3) . ?
N1 C20 1.318(3) . ?
S2 C24 1.694(3) . ?
S2 C21 1.714(2) . ?
N2 C20 1.351(3) . ?
N2 C16 1.393(3) . ?
N2 H2 0.900(17) . ?
C11 C16 1.392(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9500 . ?
C20 C21 1.457(4) . ?
C21 C22 1.420(4) . ?
C22 C23 1.425(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.363(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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 S1 N1 107.66(11) . . ?
O1 S1 C11 103.89(11) . . ?
N1 S1 C11 100.83(12) . . ?
C20 N1 S1 120.38(18) . . ?
C24 S2 C21 92.01(13) . . ?
C20 N2 C16 123.3(2) . . ?
C20 N2 H2 119.0(18) . . ?
C16 N2 H2 117.7(18) . . ?
C16 C11 C12 120.4(2) . . ?
C16 C11 S1 118.61(19) . . ?
C12 C11 S1 120.6(2) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 N2 120.4(2) . . ?
C11 C16 C15 119.6(2) . . ?
N2 C16 C15 120.0(2) . . ?
N1 C20 N2 125.3(2) . . ?
N1 C20 C21 117.2(2) . . ?
N2 C20 C21 117.5(2) . . ?
C20 C21 C22 129.6(2) . . ?
C20 C21 S2 118.40(18) . . ?
C22 C21 S2 112.04(18) . . ?
C23 C22 C21 109.5(2) . . ?
C23 C22 H22 125.3 . . ?
C21 C22 H22 125.3 . . ?
C24 C23 C22 113.9(3) . . ?
C24 C23 H23 123.1 . . ?
C22 C23 H23 123.1 . . ?
C23 C24 S2 112.6(2) . . ?
C23 C24 H24 123.7 . . ?
S2 C24 H24 123.7 . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-3


####################################################################### 
# 
# 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/. 
# 
# 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_compound_2c
_database_code_depnum_ccdc_archive 'CCDC 1027459'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 F3 N2 O S'
_chemical_formula_sum            'C14 H9 F3 N2 O S'
_chemical_formula_weight         310.29

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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)/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                   12.7488(9)
_cell_length_b                   8.6205(6)
_cell_length_c                   12.1309(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.918(3)
_cell_angle_gamma                90.00
_cell_volume                     1304.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      30.71

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
APEX-II, Bruker AXS, Madison, WI, USA. 
;

_diffrn_ambient_temperature      150(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19374
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2303
_reflns_number_gt                2232
_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)+(0.0307P)²+1.0263P] 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         2303
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_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
S1 S 0.65273(4) 0.05147(5) -0.14912(4) 0.01891(14) Uani 1 1 d . . .
C3 C 0.81232(14) 0.0631(2) 0.17610(15) 0.0185(4) Uani 1 1 d . . .
H3 H 0.8071 0.1144 0.2441 0.022 Uiso 1 1 calc R . .
C4 C 0.89713(15) -0.0362(2) 0.17263(16) 0.0210(4) Uani 1 1 d . . .
C2 C 0.73445(14) 0.0863(2) 0.07762(15) 0.0171(4) Uani 1 1 d . . .
C9 C 0.46649(14) 0.2797(2) 0.01676(15) 0.0176(4) Uani 1 1 d . . .
C8 C 0.55878(14) 0.1867(2) -0.00360(14) 0.0172(4) Uani 1 1 d . . .
C1 C 0.74515(14) 0.0124(2) -0.02162(15) 0.0184(4) Uani 1 1 d . . .
C7 C 0.97867(15) -0.0667(2) 0.27812(17) 0.0256(4) Uani 1 1 d . . .
C10 C 0.39340(15) 0.3380(2) -0.07600(15) 0.0225(4) Uani 1 1 d . . .
H10 H 0.4021 0.3146 -0.1501 0.027 Uiso 1 1 calc R . .
C14 C 0.45158(14) 0.3128(2) 0.12487(15) 0.0207(4) Uani 1 1 d . . .
H14 H 0.4993 0.2708 0.1885 0.025 Uiso 1 1 calc R . .
C6 C 0.83046(16) -0.0880(2) -0.02302(16) 0.0244(4) Uani 1 1 d . . .
H6 H 0.8358 -0.1399 -0.0908 0.029 Uiso 1 1 calc R . .
C5 C 0.90716(16) -0.1124(2) 0.07353(17) 0.0257(4) Uani 1 1 d . . .
H5 H 0.9659 -0.1798 0.0728 0.031 Uiso 1 1 calc R . .
C13 C 0.36754(15) 0.4067(2) 0.14001(17) 0.0256(4) Uani 1 1 d . . .
H13 H 0.3588 0.4309 0.2140 0.031 Uiso 1 1 calc R . .
C11 C 0.30883(16) 0.4293(2) -0.06050(17) 0.0260(4) Uani 1 1 d . . .
H11 H 0.2591 0.4675 -0.1240 0.031 Uiso 1 1 calc R . .
C12 C 0.29601(16) 0.4656(2) 0.04750(18) 0.0278(4) Uani 1 1 d . . .
H12 H 0.2386 0.5304 0.0580 0.033 Uiso 1 1 calc R . .
N1 N 0.54770(12) 0.11578(18) -0.10099(12) 0.0198(3) Uani 1 1 d . . .
N2 N 0.64702(12) 0.18136(18) 0.08019(12) 0.0175(3) Uani 1 1 d . . .
H2 H 0.6492 0.2412 0.1394 0.021 Uiso 1 1 calc R . .
F2 F 1.07833(10) -0.0670(2) 0.26028(12) 0.0504(4) Uani 1 1 d . . .
F3 F 0.97579(12) 0.03518(17) 0.35974(11) 0.0503(4) Uani 1 1 d . . .
F1 F 0.96563(11) -0.20620(16) 0.32161(11) 0.0444(4) Uani 1 1 d . . .
O1 O 0.69844(10) 0.18814(16) -0.19933(11) 0.0248(3) 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 O1 1.4984(14) . ?
S1 N1 1.6626(16) . ?
S1 C1 1.7724(18) . ?
C3 C4 1.386(3) . ?
C3 C2 1.401(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 C7 1.496(3) . ?
C2 N2 1.389(2) . ?
C2 C1 1.393(3) . ?
C9 C14 1.393(3) . ?
C9 C10 1.398(3) . ?
C9 C8 1.486(2) . ?
C8 N1 1.312(2) . ?
C8 N2 1.352(2) . ?
C1 C6 1.393(3) . ?
C7 F3 1.330(2) . ?
C7 F2 1.332(2) . ?
C7 F1 1.337(2) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C14 C13 1.385(3) . ?
C14 H14 0.9500 . ?
C6 C5 1.378(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C13 C12 1.388(3) . ?
C13 H13 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N2 H2 0.8800 . ?

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 S1 N1 106.83(8) . . ?
O1 S1 C1 105.06(8) . . ?
N1 S1 C1 101.27(8) . . ?
C4 C3 C2 118.82(17) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.75(18) . . ?
C3 C4 C7 119.42(17) . . ?
C5 C4 C7 118.81(17) . . ?
N2 C2 C1 120.75(16) . . ?
N2 C2 C3 119.72(16) . . ?
C1 C2 C3 119.52(17) . . ?
C14 C9 C10 119.08(17) . . ?
C14 C9 C8 122.26(16) . . ?
C10 C9 C8 118.65(16) . . ?
N1 C8 N2 125.39(16) . . ?
N1 C8 C9 117.35(16) . . ?
N2 C8 C9 117.26(15) . . ?
C2 C1 C6 120.72(17) . . ?
C2 C1 S1 120.06(14) . . ?
C6 C1 S1 119.17(14) . . ?
F3 C7 F2 107.23(17) . . ?
F3 C7 F1 105.99(17) . . ?
F2 C7 F1 105.24(16) . . ?
F3 C7 C4 113.55(16) . . ?
F2 C7 C4 112.27(16) . . ?
F1 C7 C4 112.00(16) . . ?
C11 C10 C9 120.38(17) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C13 C14 C9 120.29(17) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C5 C6 C1 120.20(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C6 C5 C4 118.97(18) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C14 C13 C12 120.24(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C10 C11 C12 120.32(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.64(18) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 N1 S1 121.80(13) . . ?
C8 N2 C2 123.39(15) . . ?
C8 N2 H2 118.3 . . ?
C2 N2 H2 118.3 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.047
