#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024524.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_4024524
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            'C25 H21 N3 O2 S'
_chemical_formula_weight         427.51
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.322(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5187(3)
_cell_length_b                   7.0193(2)
_cell_length_c                   22.3550(6)
_cell_measurement_reflns_used    18394
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2120.74(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0911
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30538
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0097(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.7541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                3291
_reflns_number_total             4857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900028c_si_002.cif
_cod_data_source_block           2008acc0665
_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)/n
_cod_database_code               4024524
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'
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 0.95964(4) 0.52755(8) 0.15425(3) 0.02751(17) Uani 1 1 d . . .
O1 O 1.17166(11) 0.0193(2) 0.25994(6) 0.0273(4) Uani 1 1 d . . .
O2 O 1.14550(14) 1.0262(2) -0.02933(7) 0.0397(5) Uani 1 1 d . . .
N1 N 1.31778(12) 0.3508(2) 0.11780(7) 0.0207(4) Uani 1 1 d . . .
N2 N 1.23393(12) 0.1949(2) 0.18591(7) 0.0203(4) Uani 1 1 d . . .
N3 N 1.14750(13) 0.4339(2) 0.13589(7) 0.0195(4) Uani 1 1 d . . .
C1 C 1.33586(18) 0.4716(3) 0.01638(10) 0.0308(5) Uani 1 1 d . . .
H1 H 1.2960 0.3703 0.0012 0.037 Uiso 1 1 calc R . .
C2 C 1.3773(2) 0.6058(4) -0.02253(11) 0.0409(7) Uani 1 1 d . . .
H2 H 1.3634 0.5988 -0.0643 0.049 Uiso 1 1 calc R . .
C3 C 1.4381(2) 0.7475(4) 0.00013(12) 0.0428(7) Uani 1 1 d . . .
H3 H 1.4656 0.8386 -0.0261 0.051 Uiso 1 1 calc R . .
C4 C 1.45909(19) 0.7577(3) 0.06057(12) 0.0380(6) Uani 1 1 d . . .
H4 H 1.5028 0.8533 0.0756 0.046 Uiso 1 1 calc R . .
C5 C 1.41713(17) 0.6300(3) 0.09956(11) 0.0303(5) Uani 1 1 d . . .
H5 H 1.4310 0.6377 0.1413 0.036 Uiso 1 1 calc R . .
C6 C 1.35434(16) 0.4902(3) 0.07656(9) 0.0232(5) Uani 1 1 d . . .
C7 C 1.39064(17) 0.2183(3) 0.14566(10) 0.0286(5) Uani 1 1 d . . .
H7A H 1.4474 0.2891 0.1635 0.034 Uiso 1 1 calc R . .
H7B H 1.4156 0.1271 0.1158 0.034 Uiso 1 1 calc R . .
C8 C 1.33352(15) 0.1152(3) 0.19377(10) 0.0240(5) Uani 1 1 d . . .
H8A H 1.3335 -0.0243 0.1872 0.029 Uiso 1 1 calc R . .
H8B H 1.3614 0.1429 0.2342 0.029 Uiso 1 1 calc R . .
C9 C 1.15521(15) 0.1439(3) 0.22226(9) 0.0214(5) Uani 1 1 d . . .
C10 C 1.06561(15) 0.2445(3) 0.21092(9) 0.0208(5) Uani 1 1 d . . .
C11 C 1.05948(15) 0.3921(3) 0.16939(9) 0.0203(4) Uani 1 1 d . . .
C12 C 1.23135(15) 0.3358(3) 0.14522(9) 0.0190(4) Uani 1 1 d . . .
C13 C 1.14427(15) 0.5870(3) 0.09205(9) 0.0203(4) Uani 1 1 d . . .
C14 C 1.17232(17) 0.7671(3) 0.10923(9) 0.0271(5) Uani 1 1 d . . .
H14 H 1.1919 0.7924 0.1495 0.033 Uiso 1 1 calc R . .
C15 C 1.17172(19) 0.9109(3) 0.06716(10) 0.0332(6) Uani 1 1 d . . .
H15 H 1.1918 1.0358 0.0784 0.040 Uiso 1 1 calc R . .
C16 C 1.14185(17) 0.8739(3) 0.00846(10) 0.0279(5) Uani 1 1 d . . .
C17 C 1.11235(16) 0.6926(3) -0.00803(9) 0.0250(5) Uani 1 1 d . . .
H17 H 1.0912 0.6670 -0.0480 0.030 Uiso 1 1 calc R . .
C18 C 1.11395(16) 0.5488(3) 0.03419(9) 0.0231(5) Uani 1 1 d . . .
H18 H 1.0941 0.4235 0.0232 0.028 Uiso 1 1 calc R . .
C19 C 1.1139(2) 0.9955(4) -0.09033(11) 0.0435(7) Uani 1 1 d . . .
H19A H 1.1578 0.9028 -0.1089 0.065 Uiso 1 1 calc R . .
H19B H 1.1164 1.1162 -0.1123 0.065 Uiso 1 1 calc R . .
H19C H 1.0460 0.9467 -0.0914 0.065 Uiso 1 1 calc R . .
C20 C 0.97857(16) 0.1850(3) 0.24556(9) 0.0267(5) Uani 1 1 d . . .
C21 C 0.94702(18) -0.0042(3) 0.24303(10) 0.0330(6) Uani 1 1 d . . .
H21 H 0.9817 -0.0931 0.2193 0.040 Uiso 1 1 calc R . .
C22 C 0.8660(2) -0.0641(5) 0.27461(13) 0.0493(8) Uani 1 1 d . . .
H22 H 0.8452 -0.1932 0.2722 0.059 Uiso 1 1 calc R . .
C23 C 0.8151(2) 0.0625(6) 0.30959(14) 0.0596(10) Uani 1 1 d . . .
H23 H 0.7592 0.0214 0.3311 0.072 Uiso 1 1 calc R . .
C24 C 0.8461(2) 0.2497(5) 0.31306(12) 0.0529(8) Uani 1 1 d . . .
H24 H 0.8116 0.3370 0.3375 0.063 Uiso 1 1 calc R . .
C25 C 0.92718(17) 0.3118(4) 0.28127(10) 0.0355(6) Uani 1 1 d . . .
H25 H 0.9476 0.4411 0.2839 0.043 Uiso 1 1 calc R . .
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'
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
C16 O2 C19 117.17(18) . . ?
C12 N1 C6 131.60(17) . . ?
C12 N1 C7 109.75(16) . . ?
C6 N1 C7 117.46(17) . . ?
C12 N2 C9 124.97(18) . . ?
C12 N2 C8 111.83(17) . . ?
C9 N2 C8 122.77(17) . . ?
C12 N3 C11 121.17(17) . . ?
C12 N3 C13 119.82(17) . . ?
C11 N3 C13 119.01(16) . . ?
C6 C1 C2 118.5(2) . . ?
C3 C2 C1 119.9(2) . . ?
C2 C3 C4 120.4(2) . . ?
C3 C4 C5 120.5(2) . . ?
C4 C5 C6 118.8(2) . . ?
C1 C6 C5 121.8(2) . . ?
C1 C6 N1 120.4(2) . . ?
C5 C6 N1 117.34(19) . . ?
N1 C7 C8 104.62(17) . . ?
N2 C8 C7 102.32(16) . . ?
O1 C9 N2 116.82(18) . . ?
O1 C9 C10 128.0(2) . . ?
N2 C9 C10 115.18(18) . . ?
C11 C10 C9 121.78(19) . . ?
C11 C10 C20 121.46(18) . . ?
C9 C10 C20 116.76(18) . . ?
C10 C11 N3 117.24(18) . . ?
C10 C11 S1 126.22(17) . . ?
N3 C11 S1 116.54(14) . . ?
N1 C12 N3 129.39(18) . . ?
N1 C12 N2 111.05(17) . . ?
N3 C12 N2 119.52(19) . . ?
C18 C13 C14 121.20(19) . . ?
C18 C13 N3 119.57(18) . . ?
C14 C13 N3 119.23(17) . . ?
C13 C14 C15 119.08(19) . . ?
C14 C15 C16 120.3(2) . . ?
O2 C16 C17 124.82(19) . . ?
O2 C16 C15 115.1(2) . . ?
C17 C16 C15 120.0(2) . . ?
C16 C17 C18 119.40(19) . . ?
C13 C18 C17 120.0(2) . . ?
C25 C20 C21 118.4(2) . . ?
C25 C20 C10 122.1(2) . . ?
C21 C20 C10 119.5(2) . . ?
C22 C21 C20 120.9(3) . . ?
C23 C22 C21 120.4(3) . . ?
C22 C23 C24 119.4(3) . . ?
C23 C24 C25 120.8(3) . . ?
C24 C25 C20 120.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.679(2) . ?
O1 C9 1.231(2) . ?
O2 C16 1.364(3) . ?
O2 C19 1.436(3) . ?
N1 C12 1.336(3) . ?
N1 C6 1.440(3) . ?
N1 C7 1.481(3) . ?
N2 C12 1.344(3) . ?
N2 C9 1.400(3) . ?
N2 C8 1.465(3) . ?
N3 C12 1.338(3) . ?
N3 C11 1.450(3) . ?
N3 C13 1.455(3) . ?
C1 C6 1.369(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.381(3) . ?
C5 C6 1.388(3) . ?
C7 C8 1.522(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.392(3) . ?
C10 C20 1.484(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.382(3) . ?
C20 C25 1.392(3) . ?
C20 C21 1.396(3) . ?
C21 C22 1.382(4) . ?
C22 C23 1.378(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.390(4) . ?
