#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024523.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024523
loop_
_publ_author_name
'David Cantillo'
'Martín Ávalos'
'Reyes Babiano'
'Pedro Cintas'
'José L. Jiménez'
'Mark E. Light'
'Juan C. Palacios'
_publ_section_title
;
Thionation of Mesoionics with Isothiocyanates: Evidence Supporting a
Four-Step Domino Process and Ruling Out a [2 + 2] Mechanism
;
_journal_coden_Cambridge         1078
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3698
_journal_page_last               3705
_journal_paper_doi               10.1021/jo900028c
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'Pedro Cintas'
_chemical_formula_sum            'C17 H14 N2 S2'
_chemical_formula_weight         310.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.5480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.59720(10)
_cell_length_b                   30.8725(6)
_cell_length_c                   12.6752(2)
_cell_measurement_reflns_used    29150
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2890.17(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37144
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.8398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1189P)²+0.7052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                3878
_reflns_number_total             6613
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900028c_si_001.cif
_cod_data_source_block           2008acc0214
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024523
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6953(4) 0.28903(10) 0.5253(3) 0.0541(8) Uani 1 1 d . . .
H1 H 0.6826 0.2919 0.4508 0.065 Uiso 1 1 calc R . .
C2 C 0.7606(5) 0.25086(10) 0.5763(3) 0.0619(9) Uani 1 1 d . . .
H2 H 0.7901 0.2281 0.5356 0.074 Uiso 1 1 calc R . .
C3 C 0.7824(5) 0.24606(12) 0.6855(3) 0.0666(10) Uani 1 1 d . . .
H3 H 0.8262 0.2202 0.7192 0.080 Uiso 1 1 calc R . .
C4 C 0.7395(5) 0.27961(13) 0.7449(3) 0.0688(10) Uani 1 1 d . . .
H4 H 0.7554 0.2765 0.8195 0.083 Uiso 1 1 calc R . .
C5 C 0.6723(4) 0.31838(11) 0.6958(2) 0.0564(8) Uani 1 1 d . . .
H5 H 0.6434 0.3410 0.7372 0.068 Uiso 1 1 calc R . .
C6 C 0.6488(4) 0.32301(9) 0.5845(2) 0.0421(7) Uani 1 1 d . . .
C7 C 0.5286(4) 0.39956(10) 0.5991(2) 0.0461(7) Uani 1 1 d . . .
H7A H 0.6299 0.4082 0.6574 0.055 Uiso 1 1 calc R . .
H7B H 0.4276 0.3917 0.6299 0.055 Uiso 1 1 calc R . .
C8 C 0.4757(4) 0.43610(9) 0.5164(2) 0.0461(7) Uani 1 1 d . . .
H8A H 0.3540 0.4464 0.5134 0.055 Uiso 1 1 calc R . .
H8B H 0.5596 0.4602 0.5328 0.055 Uiso 1 1 calc R . .
C9 C 0.5498(3) 0.37456(9) 0.4317(2) 0.0370(6) Uani 1 1 d . . .
C10 C 0.4508(4) 0.43061(9) 0.3079(2) 0.0391(6) Uani 1 1 d . . .
C11 C 0.4907(3) 0.39867(8) 0.2405(2) 0.0380(6) Uani 1 1 d . . .
C12 C 0.4747(4) 0.39810(9) 0.1226(2) 0.0397(6) Uani 1 1 d . . .
C13 C 0.4141(4) 0.43399(11) 0.0571(2) 0.0531(8) Uani 1 1 d . . .
H13 H 0.3829 0.4593 0.0879 0.064 Uiso 1 1 calc R . .
C14 C 0.4003(5) 0.43200(13) -0.0534(3) 0.0651(10) Uani 1 1 d . . .
H14 H 0.3629 0.4564 -0.0957 0.078 Uiso 1 1 calc R . .
C15 C 0.4404(5) 0.39482(13) -0.1020(3) 0.0653(10) Uani 1 1 d . . .
H15 H 0.4260 0.3936 -0.1768 0.078 Uiso 1 1 calc R . .
C16 C 0.5013(5) 0.35970(12) -0.0395(3) 0.0623(9) Uani 1 1 d . . .
H16 H 0.5317 0.3346 -0.0716 0.075 Uiso 1 1 calc R . .
C17 C 0.5187(4) 0.36103(11) 0.0719(2) 0.0506(7) Uani 1 1 d . . .
H17 H 0.5606 0.3367 0.1135 0.061 Uiso 1 1 calc R . .
C18 C 0.0064(4) 0.37460(11) 0.0708(2) 0.0555(8) Uani 1 1 d . . .
H18 H 0.0464 0.3537 0.1239 0.067 Uiso 1 1 calc R . .
C19 C 0.0062(5) 0.36587(13) -0.0361(3) 0.0629(9) Uani 1 1 d . . .
H19 H 0.0460 0.3390 -0.0545 0.075 Uiso 1 1 calc R . .
C20 C -0.0519(4) 0.39621(14) -0.1152(3) 0.0657(10) Uani 1 1 d . . .
H20 H -0.0514 0.3902 -0.1870 0.079 Uiso 1 1 calc R . .
C21 C -0.1109(5) 0.43551(13) -0.0875(3) 0.0658(10) Uani 1 1 d . . .
H21 H -0.1512 0.4561 -0.1413 0.079 Uiso 1 1 calc R . .
C22 C -0.1117(4) 0.44531(11) 0.0187(3) 0.0564(8) Uani 1 1 d . . .
H22 H -0.1514 0.4723 0.0362 0.068 Uiso 1 1 calc R . .
C23 C -0.0530(4) 0.41460(10) 0.0993(2) 0.0439(7) Uani 1 1 d . . .
C24 C -0.1201(4) 0.46737(9) 0.2402(2) 0.0493(7) Uani 1 1 d . . .
H24A H -0.2474 0.4716 0.2068 0.059 Uiso 1 1 calc R . .
H24B H -0.0515 0.4910 0.2191 0.059 Uiso 1 1 calc R . .
C25 C -0.0886(4) 0.46488(9) 0.3633(2) 0.0498(7) Uani 1 1 d . . .
H25A H 0.0029 0.4855 0.3987 0.060 Uiso 1 1 calc R . .
H25B H -0.1995 0.4702 0.3866 0.060 Uiso 1 1 calc R . .
C26 C -0.0059(3) 0.40034(8) 0.2961(2) 0.0375(6) Uani 1 1 d . . .
C27 C 0.0229(4) 0.39671(9) 0.4839(2) 0.0388(6) Uani 1 1 d . . .
C28 C 0.0822(4) 0.35612(9) 0.4632(2) 0.0391(6) Uani 1 1 d . . .
C29 C 0.1462(4) 0.31939(9) 0.5348(2) 0.0412(6) Uani 1 1 d . . .
C30 C 0.1607(4) 0.32152(10) 0.6469(2) 0.0518(8) Uani 1 1 d . . .
H30 H 0.1300 0.3469 0.6778 0.062 Uiso 1 1 calc R . .
C31 C 0.2205(5) 0.28597(12) 0.7119(3) 0.0646(9) Uani 1 1 d . . .
H31 H 0.2286 0.2878 0.7861 0.077 Uiso 1 1 calc R . .
C32 C 0.2682(5) 0.24818(12) 0.6693(3) 0.0669(10) Uani 1 1 d . . .
H32 H 0.3084 0.2246 0.7140 0.080 Uiso 1 1 calc R . .
C33 C 0.2560(5) 0.24558(10) 0.5599(3) 0.0648(10) Uani 1 1 d . . .
H33 H 0.2882 0.2201 0.5300 0.078 Uiso 1 1 calc R . .
C34 C 0.1962(4) 0.28058(10) 0.4940(3) 0.0549(8) Uani 1 1 d . . .
H34 H 0.1890 0.2782 0.4200 0.066 Uiso 1 1 calc R . .
N1 N 0.5801(3) 0.36271(7) 0.53637(18) 0.0415(5) Uani 1 1 d . . .
N2 N 0.4868(3) 0.41468(7) 0.41505(17) 0.0388(5) Uani 1 1 d . . .
N3 N -0.0565(3) 0.42507(7) 0.20750(19) 0.0430(6) Uani 1 1 d . . .
N4 N -0.0262(3) 0.42010(7) 0.38610(18) 0.0388(5) Uani 1 1 d . . .
S1 S 0.57191(9) 0.35104(2) 0.31439(5) 0.0402(2) Uani 1 1 d . . .
S2 S 0.37527(12) 0.48240(3) 0.28559(6) 0.0554(3) Uani 1 1 d . . .
S3 S 0.07787(9) 0.34950(2) 0.32336(5) 0.0402(2) Uani 1 1 d . . .
S4 S 0.00368(12) 0.42202(3) 0.60012(6) 0.0547(3) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.2(3) . . ?
C3 C2 C1 120.9(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 121.2(3) . . ?
C6 C5 C4 119.3(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 N1 122.6(3) . . ?
C5 C6 N1 118.4(3) . . ?
N1 C7 C8 104.9(2) . . ?
N2 C8 C7 102.0(2) . . ?
N2 C9 N1 112.6(2) . . ?
N2 C9 S1 111.43(19) . . ?
N1 C9 S1 136.0(2) . . ?
C11 C10 N2 109.0(2) . . ?
C11 C10 S2 133.0(2) . . ?
N2 C10 S2 118.03(19) . . ?
C10 C11 C12 131.1(3) . . ?
C10 C11 S1 111.32(19) . . ?
C12 C11 S1 117.5(2) . . ?
C17 C12 C13 117.3(3) . . ?
C17 C12 C11 120.5(3) . . ?
C13 C12 C11 122.2(3) . . ?
C14 C13 C12 120.3(3) . . ?
C15 C14 C13 121.4(3) . . ?
C16 C15 C14 119.2(3) . . ?
C15 C16 C17 120.5(3) . . ?
C16 C17 C12 121.2(3) . . ?
C19 C18 C23 120.1(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 119.2(3) . . ?
C20 C21 C22 121.4(3) . . ?
C21 C22 C23 119.5(3) . . ?
C22 C23 C18 118.9(3) . . ?
C22 C23 N3 118.7(3) . . ?
C18 C23 N3 122.3(3) . . ?
N3 C24 C25 104.9(2) . . ?
N4 C25 C24 102.4(2) . . ?
N4 C26 N3 112.9(2) . . ?
N4 C26 S3 111.2(2) . . ?
N3 C26 S3 135.9(2) . . ?
C28 C27 N4 109.3(2) . . ?
C28 C27 S4 132.8(2) . . ?
N4 C27 S4 117.9(2) . . ?
C27 C28 C29 131.6(3) . . ?
C27 C28 S3 111.3(2) . . ?
C29 C28 S3 117.1(2) . . ?
C34 C29 C30 117.0(3) . . ?
C34 C29 C28 121.1(3) . . ?
C30 C29 C28 121.9(3) . . ?
C31 C30 C29 120.2(3) . . ?
C32 C31 C30 121.4(3) . . ?
C31 C32 C33 119.2(3) . . ?
C32 C33 C34 120.2(3) . . ?
C33 C34 C29 122.0(3) . . ?
C9 N1 C6 128.6(2) . . ?
C9 N1 C7 108.2(2) . . ?
C6 N1 C7 123.2(2) . . ?
C9 N2 C10 117.4(2) . . ?
C9 N2 C8 112.0(2) . . ?
C10 N2 C8 130.5(2) . . ?
C26 N3 C23 128.1(2) . . ?
C26 N3 C24 108.4(2) . . ?
C23 N3 C24 123.5(2) . . ?
C26 N4 C27 117.3(2) . . ?
C26 N4 C25 111.1(2) . . ?
C27 N4 C25 131.5(2) . . ?
C9 S1 C11 90.84(12) . . ?
C26 S3 C28 90.86(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(4) . ?
C1 C6 1.383(4) . ?
C2 C3 1.364(5) . ?
C3 C4 1.364(5) . ?
C4 C5 1.390(5) . ?
C5 C6 1.388(4) . ?
C6 N1 1.413(3) . ?
C7 N1 1.492(3) . ?
C7 C8 1.528(4) . ?
C8 N2 1.465(3) . ?
C9 N2 1.327(3) . ?
C9 N1 1.343(3) . ?
C9 S1 1.698(3) . ?
C10 C11 1.384(4) . ?
C10 N2 1.410(3) . ?
C10 S2 1.700(3) . ?
C11 C12 1.470(4) . ?
C11 S1 1.775(3) . ?
C12 C17 1.391(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.370(5) . ?
C15 C16 1.359(5) . ?
C16 C17 1.387(4) . ?
C18 C19 1.381(4) . ?
C18 C23 1.391(4) . ?
C19 C20 1.368(5) . ?
C20 C21 1.367(5) . ?
C21 C22 1.382(5) . ?
C22 C23 1.388(4) . ?
C23 N3 1.416(3) . ?
C24 N3 1.485(4) . ?
C24 C25 1.525(4) . ?
C25 N4 1.468(3) . ?
C26 N4 1.334(3) . ?
C26 N3 1.338(3) . ?
C26 S3 1.698(3) . ?
C27 C28 1.377(4) . ?
C27 N4 1.407(3) . ?
C27 S4 1.704(3) . ?
C28 C29 1.462(4) . ?
C28 S3 1.777(3) . ?
C29 C34 1.393(4) . ?
C29 C30 1.401(4) . ?
C30 C31 1.384(4) . ?
C31 C32 1.370(5) . ?
C32 C33 1.370(5) . ?
C33 C34 1.376(4) . ?
