# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# 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.
#
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# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
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# data retrieval see:
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data_no_68
_database_code_depnum_ccdc_archive 'CCDC 873353'
#TrackingRef 'CCDC12_5.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H8 N2 S3'
_chemical_formula_sum 'C15 H8 N2 S3'
_chemical_formula_weight 312.44
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'
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/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 12.1083(8)
_cell_length_b 8.4579(4)
_cell_length_c 13.1468(9)
_cell_angle_alpha 90.00
_cell_angle_beta 90.114(5)
_cell_angle_gamma 90.00
_cell_volume 1346.37(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 291(2)
_cell_measurement_reflns_used 12763
_cell_measurement_theta_min 2.28
_cell_measurement_theta_max 29.70
_exptl_crystal_description prismatic
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.43
_exptl_crystal_size_mid 0.41
_exptl_crystal_size_min 0.26
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.541
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.539
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 291(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 'Xcalibur, Eos'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 32.3
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_diffrn_reflns_number 9624
_diffrn_reflns_av_R_equivalents 0.0399
_diffrn_reflns_av_sigmaI/netI 0.0240
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.28
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2357
_reflns_number_gt 2212
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_cell_refinement
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_data_reduction
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 1998)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0662P)^2^+0.5813P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2357
_refine_ls_number_parameters 181
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0392
_refine_ls_R_factor_gt 0.0365
_refine_ls_wR_factor_ref 0.1050
_refine_ls_wR_factor_gt 0.1027
_refine_ls_goodness_of_fit_ref 0.993
_refine_ls_restrained_S_all 0.993
_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 0.59284(5) -0.06953(7) 0.10153(4) 0.04891(19) Uani 1 1 d . . .
S2 S 0.40143(4) 0.14646(8) 0.16625(4) 0.0536(2) Uani 1 1 d . . .
S3 S 0.81473(5) 0.03289(8) 0.00879(4) 0.0576(2) Uani 1 1 d . . .
N1 N 0.69860(13) 0.1030(2) 0.28342(12) 0.0446(4) Uani 1 1 d . . .
N2 N 0.86742(19) -0.2005(3) 0.73475(18) 0.0727(6) Uani 1 1 d . . .
C1 C 0.53151(17) 0.0691(2) 0.18358(15) 0.0414(5) Uani 1 1 d . . .
C2 C 0.58532(16) 0.1389(2) 0.26244(14) 0.0395(4) Uani 1 1 d . . .
C3 C 0.76508(16) 0.0881(3) 0.19422(15) 0.0425(5) Uani 1 1 d . . .
C4 C 0.72541(17) 0.0139(2) 0.10992(15) 0.0426(5) Uani 1 1 d . . .
C5 C 0.41940(19) 0.2726(3) 0.26684(16) 0.0495(5) Uani 1 1 d . . .
H51 H 0.3655 0.3425 0.2895 0.059 Uiso 1 1 calc R . .
C6 C 0.52076(17) 0.2593(2) 0.30961(15) 0.0443(5) Uani 1 1 d . . .
H61 H 0.5454 0.3213 0.3635 0.053 Uiso 1 1 calc R . .
C7 C 0.9065(2) 0.1356(3) 0.0831(2) 0.0591(6) Uani 1 1 d . . .
H71 H 0.9746 0.1713 0.0599 0.071 Uiso 1 1 calc R . .
C8 C 0.86980(19) 0.1594(3) 0.17858(18) 0.0524(5) Uani 1 1 d . . .
H81 H 0.9083 0.2155 0.2281 0.063 Uiso 1 1 calc R . .
C9 C 0.73449(16) 0.0476(2) 0.37792(15) 0.0399(4) Uani 1 1 d . . .
C10 C 0.83700(17) -0.0275(3) 0.38782(16) 0.0484(5) Uani 1 1 d . . .
H101 H 0.8829 -0.0364 0.3315 0.058 Uiso 1 1 calc R . .
C11 C 0.87066(18) -0.0883(3) 0.47949(18) 0.0501(5) Uani 1 1 d . . .
H111 H 0.9382 -0.1401 0.4840 0.060 Uiso 1 1 calc R . .
C12 C 0.80536(18) -0.0735(2) 0.56558(16) 0.0462(5) Uani 1 1 d . . .
C13 C 0.70417(18) 0.0037(3) 0.55749(16) 0.0505(5) Uani 1 1 d . . .
H131 H 0.6601 0.0160 0.6148 0.061 Uiso 1 1 calc R . .
C14 C 0.66882(19) 0.0621(3) 0.46518(16) 0.0487(5) Uani 1 1 d . . .
H141 H 0.6005 0.1117 0.4607 0.058 Uiso 1 1 calc R . .
C15 C 0.84015(18) -0.1433(3) 0.66055(19) 0.0533(5) 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
S1 0.0486(3) 0.0546(3) 0.0435(3) -0.0129(2) -0.0051(2) 0.0078(2)
S2 0.0437(3) 0.0706(4) 0.0465(3) -0.0049(3) -0.0042(2) 0.0142(3)
S3 0.0615(4) 0.0726(4) 0.0386(3) 0.0093(2) 0.0141(2) 0.0203(3)
N1 0.0355(8) 0.0616(11) 0.0366(9) -0.0071(8) 0.0036(7) 0.0035(8)
N2 0.0589(13) 0.0926(17) 0.0667(14) 0.0216(13) -0.0086(10) 0.0039(12)
C1 0.0410(10) 0.0451(11) 0.0381(10) 0.0002(8) 0.0002(8) 0.0054(8)
C2 0.0371(10) 0.0453(11) 0.0360(9) 0.0007(8) 0.0045(8) 0.0005(8)
C3 0.0399(10) 0.0468(11) 0.0408(10) -0.0002(8) 0.0066(8) 0.0051(9)
C4 0.0453(11) 0.0471(11) 0.0356(10) 0.0031(8) 0.0050(8) 0.0121(9)
C5 0.0492(12) 0.0522(12) 0.0472(11) 0.0016(9) 0.0109(9) 0.0111(10)
C6 0.0466(11) 0.0451(11) 0.0413(10) -0.0042(9) 0.0091(8) -0.0003(9)
C7 0.0524(13) 0.0562(13) 0.0689(15) 0.0132(11) 0.0228(11) 0.0059(11)
C8 0.0463(12) 0.0495(12) 0.0615(13) -0.0028(10) 0.0106(10) 0.0007(10)
C9 0.0395(10) 0.0422(10) 0.0380(10) -0.0079(8) 0.0010(8) -0.0023(8)
C10 0.0422(11) 0.0561(12) 0.0470(12) -0.0094(9) 0.0054(9) 0.0027(10)
C11 0.0413(11) 0.0517(12) 0.0574(13) -0.0036(10) -0.0018(9) 0.0044(10)
C12 0.0471(11) 0.0438(11) 0.0477(11) -0.0010(9) -0.0044(9) -0.0040(9)
C13 0.0511(13) 0.0580(13) 0.0423(11) 0.0000(10) 0.0065(9) 0.0033(11)
C14 0.0453(11) 0.0578(13) 0.0429(11) 0.0009(9) 0.0048(9) 0.0097(10)
C15 0.0434(11) 0.0580(13) 0.0584(14) 0.0040(11) -0.0021(10) -0.0029(10)
_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 C4 1.757(2) . ?
S1 C1 1.759(2) . ?
S2 C5 1.713(2) . ?
S2 C1 1.720(2) . ?
S3 C4 1.723(2) . ?
S3 C7 1.715(3) . ?
N1 C9 1.396(3) . ?
N1 C3 1.429(2) . ?
N1 C2 1.431(2) . ?
N2 C15 1.137(3) . ?
C1 C2 1.358(3) . ?
C2 C6 1.426(3) . ?
C3 C4 1.361(3) . ?
C3 C8 1.419(3) . ?
C5 C6 1.354(3) . ?
C5 H51 0.9300 . ?
C6 H61 0.9300 . ?
C7 C8 1.348(3) . ?
C7 H71 0.9300 . ?
C8 H81 0.9300 . ?
C9 C10 1.400(3) . ?
C9 C14 1.402(3) . ?
C10 C11 1.371(3) . ?
C10 H101 0.9300 . ?
C11 C12 1.388(3) . ?
C11 H111 0.9300 . ?
C12 C13 1.392(3) . ?
C12 C15 1.443(3) . ?
C13 C14 1.377(3) . ?
C13 H131 0.9300 . ?
C14 H141 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
C4 S1 C1 94.63(10) . . ?
C5 S2 C1 91.14(10) . . ?
C4 S3 C7 90.87(11) . . ?
C9 N1 C3 121.71(17) . . ?
C9 N1 C2 122.63(16) . . ?
C3 N1 C2 113.68(16) . . ?
C2 C1 S2 111.92(15) . . ?
C2 C1 S1 123.74(16) . . ?
S2 C1 S1 124.05(12) . . ?
C1 C2 C6 112.31(18) . . ?
C1 C2 N1 120.86(18) . . ?
C6 C2 N1 126.41(18) . . ?
C4 C3 C8 113.08(19) . . ?
C4 C3 N1 120.71(18) . . ?
C8 C3 N1 125.88(19) . . ?
C3 C4 S3 111.37(16) . . ?
C3 C4 S1 123.88(15) . . ?
S3 C4 S1 124.33(12) . . ?
C6 C5 S2 112.48(16) . . ?
C6 C5 H51 123.8 . . ?
S2 C5 H51 123.8 . . ?
C5 C6 C2 112.10(19) . . ?
C5 C6 H61 123.9 . . ?
C2 C6 H61 123.9 . . ?
C8 C7 S3 113.03(19) . . ?
C8 C7 H71 123.5 . . ?
S3 C7 H71 123.5 . . ?
C7 C8 C3 111.6(2) . . ?
C7 C8 H81 124.2 . . ?
C3 C8 H81 124.2 . . ?
N1 C9 C10 120.61(18) . . ?
N1 C9 C14 121.51(18) . . ?
C10 C9 C14 117.86(19) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H101 119.5 . . ?
C9 C10 H101 119.5 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H111 119.5 . . ?
C12 C11 H111 119.5 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 C15 120.2(2) . . ?
C13 C12 C15 120.9(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H131 119.8 . . ?
C12 C13 H131 119.8 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H141 119.5 . . ?
C9 C14 H141 119.5 . . ?
N2 C15 C12 179.0(3) . . ?
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
C5 S2 C1 C2 -0.50(17) . . . . ?
C5 S2 C1 S1 -174.58(15) . . . . ?
C4 S1 C1 C2 -31.8(2) . . . . ?
C4 S1 C1 S2 141.55(14) . . . . ?
S2 C1 C2 C6 -0.7(2) . . . . ?
S1 C1 C2 C6 173.41(15) . . . . ?
S2 C1 C2 N1 -173.75(15) . . . . ?
S1 C1 C2 N1 0.4(3) . . . . ?
C9 N1 C2 C1 -124.0(2) . . . . ?
C3 N1 C2 C1 40.2(3) . . . . ?
C9 N1 C2 C6 64.0(3) . . . . ?
C3 N1 C2 C6 -131.8(2) . . . . ?
C9 N1 C3 C4 124.1(2) . . . . ?
C2 N1 C3 C4 -40.3(3) . . . . ?
C9 N1 C3 C8 -63.0(3) . . . . ?
C2 N1 C3 C8 132.6(2) . . . . ?
C8 C3 C4 S3 -1.1(2) . . . . ?
N1 C3 C4 S3 172.68(16) . . . . ?
C8 C3 C4 S1 -173.91(16) . . . . ?
N1 C3 C4 S1 -0.2(3) . . . . ?
C7 S3 C4 C3 1.80(17) . . . . ?
C7 S3 C4 S1 174.59(15) . . . . ?
C1 S1 C4 C3 31.8(2) . . . . ?
C1 S1 C4 S3 -140.14(14) . . . . ?
C1 S2 C5 C6 1.64(18) . . . . ?
S2 C5 C6 C2 -2.3(2) . . . . ?
C1 C2 C6 C5 1.9(3) . . . . ?
N1 C2 C6 C5 174.53(19) . . . . ?
C4 S3 C7 C8 -2.15(19) . . . . ?
S3 C7 C8 C3 1.9(3) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
N1 C3 C8 C7 -173.9(2) . . . . ?
C3 N1 C9 C10 -1.2(3) . . . . ?
C2 N1 C9 C10 161.81(19) . . . . ?
C3 N1 C9 C14 -179.8(2) . . . . ?
C2 N1 C9 C14 -16.8(3) . . . . ?
N1 C9 C10 C11 -177.2(2) . . . . ?
C14 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C10 C11 C12 C15 177.6(2) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C15 C12 C13 C14 -176.3(2) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
N1 C9 C14 C13 178.5(2) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C11 C12 C15 N2 -65(14) . . . . ?
C13 C12 C15 N2 112(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.320
_refine_diff_density_min -0.309
_refine_diff_density_rms 0.044