#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024901.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_4024901
loop_
_publ_author_name
'David Cantillo'
'Martín Ávalos'
'Reyes Babiano'
'Pedro Cintas'
'José L. Jiménez'
'Mark E. Light'
'Juan C. Palacios'
_publ_section_title
;
Dissecting Competitive Mechanisms: Thionation vs. Cycloaddition in the
Reaction of Thioisomünchnones with Isothiocyanates under Microwave
Irradiation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7644
_journal_page_last               7650
_journal_paper_doi               10.1021/jo900960a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C26 H23 N2 S2'
_chemical_formula_weight         427.58
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.779(2)
_cell_angle_beta                 101.894(2)
_cell_angle_gamma                97.749(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4168(3)
_cell_length_b                   9.8111(2)
_cell_length_c                   11.9374(4)
_cell_measurement_reflns_used    4743
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1057.19(5)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21657
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.7313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                3664
_reflns_number_total             4838
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo900960a_si_001.cif
_cod_data_source_block           2007acc0548
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4024901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.45114(5) 0.39502(5) 0.14420(4) 0.01789(13) Uani 1 1 d . . .
S2 S 0.73717(5) 0.25611(6) -0.06512(5) 0.02420(15) Uani 1 1 d . . .
N1 N 0.21400(17) 0.23751(17) 0.00473(14) 0.0191(4) Uani 1 1 d . . .
C8 C 0.3595(2) 0.2779(2) 0.02359(17) 0.0170(4) Uani 1 1 d . . .
N2 N 0.45378(17) 0.24026(16) -0.04161(14) 0.0170(3) Uani 1 1 d . . .
C17 C 0.4151(2) 0.1400(2) -0.14684(17) 0.0173(4) Uani 1 1 d . . .
C9 C 0.6068(2) 0.3043(2) 0.00413(17) 0.0172(4) Uani 1 1 d . . .
C11 C 0.7520(2) 0.47111(19) 0.18734(17) 0.0164(4) Uani 1 1 d . . .
C7 C 0.1392(2) 0.2857(2) 0.09472(17) 0.0203(4) Uani 1 1 d . . .
H7A H 0.0365 0.2915 0.0574 0.024 Uiso 1 1 calc R . .
H7B H 0.1883 0.3808 0.1314 0.024 Uiso 1 1 calc R . .
C10 C 0.6206(2) 0.3928(2) 0.10513(17) 0.0165(4) Uani 1 1 d . . .
C21 C 0.3545(2) -0.0948(2) -0.2430(2) 0.0288(5) Uani 1 1 d . . .
H21 H 0.3345 -0.1917 -0.2404 0.035 Uiso 1 1 calc R . .
C12 C 0.7522(2) 0.5006(2) 0.30539(18) 0.0223(4) Uani 1 1 d . . .
H12 H 0.6661 0.4698 0.3312 0.027 Uiso 1 1 calc R . .
C16 C 0.8813(2) 0.5197(2) 0.15227(18) 0.0213(4) Uani 1 1 d . . .
H16 H 0.8842 0.5025 0.0728 0.026 Uiso 1 1 calc R . .
C5 C 0.2199(2) 0.0875(2) 0.20109(18) 0.0229(4) Uani 1 1 d . . .
H5 H 0.2826 0.0705 0.1498 0.027 Uiso 1 1 calc R . .
C13 C 0.8758(2) 0.5737(2) 0.38531(19) 0.0259(5) Uani 1 1 d . . .
H13 H 0.8735 0.5923 0.4648 0.031 Uiso 1 1 calc R . .
C15 C 1.0042(2) 0.5921(2) 0.2322(2) 0.0254(5) Uani 1 1 d . . .
H15 H 1.0906 0.6234 0.2070 0.030 Uiso 1 1 calc R . .
C23 C 0.1218(2) 0.1378(3) -0.0930(2) 0.0326(5) Uani 1 1 d . . .
H23A H 0.1490 0.1579 -0.1650 0.049 Uiso 1 1 calc R . .
H23B H 0.0181 0.1458 -0.0980 0.049 Uiso 1 1 calc R . .
H23C H 0.1367 0.0431 -0.0811 0.049 Uiso 1 1 calc R . .
C6 C 0.1369(2) 0.1940(2) 0.18889(17) 0.0191(4) Uani 1 1 d . . .
C4 C 0.2119(2) 0.0052(2) 0.28794(19) 0.0261(5) Uani 1 1 d . . .
H4 H 0.2681 -0.0680 0.2950 0.031 Uiso 1 1 calc R . .
C1 C 0.0466(2) 0.2185(2) 0.26570(18) 0.0236(4) Uani 1 1 d . . .
H1 H -0.0107 0.2910 0.2583 0.028 Uiso 1 1 calc R . .
C18 C 0.4123(2) 0.1878(2) -0.25159(18) 0.0244(5) Uani 1 1 d . . .
H18 H 0.4327 0.2847 -0.2543 0.029 Uiso 1 1 calc R . .
C3 C 0.1222(2) 0.0302(2) 0.36392(19) 0.0278(5) Uani 1 1 d . . .
H3 H 0.1169 -0.0256 0.4232 0.033 Uiso 1 1 calc R . .
C14 C 1.0027(2) 0.6197(2) 0.34916(19) 0.0259(5) Uani 1 1 d . . .
H14 H 1.0875 0.6693 0.4035 0.031 Uiso 1 1 calc R . .
C22 C 0.3866(2) -0.0007(2) -0.14112(18) 0.0234(4) Uani 1 1 d . . .
H22 H 0.3889 -0.0325 -0.0687 0.028 Uiso 1 1 calc R . .
C20 C 0.3516(2) -0.0483(2) -0.3480(2) 0.0303(5) Uani 1 1 d . . .
H20 H 0.3304 -0.1133 -0.4172 0.036 Uiso 1 1 calc R . .
C19 C 0.3795(3) 0.0926(2) -0.3528(2) 0.0317(5) Uani 1 1 d . . .
H19 H 0.3762 0.1244 -0.4253 0.038 Uiso 1 1 calc R . .
C2 C 0.0401(2) 0.1372(2) 0.35309(19) 0.0276(5) Uani 1 1 d . . .
H2 H -0.0209 0.1550 0.4056 0.033 Uiso 1 1 calc R . .
C25 C 0.3706(2) 0.4816(2) 0.41482(19) 0.0270(5) Uani 1 1 d . . .
H25 H 0.2825 0.4691 0.3565 0.032 Uiso 1 1 calc R . .
C26 C 0.4431(2) 0.6150(2) 0.46392(19) 0.0284(5) Uani 1 1 d . . .
H26 H 0.4041 0.6938 0.4396 0.034 Uiso 1 1 calc R . .
C24 C 0.4274(2) 0.3671(2) 0.45144(19) 0.0287(5) Uani 1 1 d . . .
H24 H 0.3776 0.2759 0.4185 0.034 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'
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
C8 S1 C10 92.12(9) . . ?
C8 N1 C23 126.28(17) . . ?
C8 N1 C7 117.90(17) . . ?
C23 N1 C7 115.54(16) . . ?
N1 C8 N2 128.99(18) . . ?
N1 C8 S1 120.18(15) . . ?
N2 C8 S1 110.83(14) . . ?
C8 N2 C17 125.60(16) . . ?
C8 N2 C9 114.94(16) . . ?
C17 N2 C9 119.40(15) . . ?
C22 C17 C18 121.19(19) . . ?
C22 C17 N2 120.11(17) . . ?
C18 C17 N2 118.66(17) . . ?
C10 C9 N2 110.31(16) . . ?
C10 C9 S2 130.41(15) . . ?
N2 C9 S2 119.18(14) . . ?
C12 C11 C16 117.57(18) . . ?
C12 C11 C10 120.27(17) . . ?
C16 C11 C10 122.16(18) . . ?
N1 C7 C6 114.66(16) . . ?
C9 C10 C11 130.61(17) . . ?
C9 C10 S1 111.79(14) . . ?
C11 C10 S1 117.28(14) . . ?
C20 C21 C22 120.4(2) . . ?
C13 C12 C11 121.42(19) . . ?
C15 C16 C11 120.78(19) . . ?
C6 C5 C4 120.6(2) . . ?
C14 C13 C12 120.1(2) . . ?
C16 C15 C14 120.88(19) . . ?
C5 C6 C1 119.03(19) . . ?
C5 C6 C7 123.00(18) . . ?
C1 C6 C7 117.96(17) . . ?
C3 C4 C5 120.1(2) . . ?
C2 C1 C6 120.2(2) . . ?
C17 C18 C19 119.3(2) . . ?
C4 C3 C2 119.7(2) . . ?
C13 C14 C15 119.2(2) . . ?
C17 C22 C21 118.90(19) . . ?
C21 C20 C19 120.2(2) . . ?
C20 C19 C18 120.0(2) . . ?
C3 C2 C1 120.4(2) . . ?
C24 C25 C26 119.7(2) . . ?
C24 C26 C25 120.0(2) 2_666 . ?
C25 C24 C26 120.3(2) . 2_666 ?
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 C8 1.723(2) . ?
S1 C10 1.7545(19) . ?
S2 C9 1.7019(19) . ?
N1 C8 1.338(2) . ?
N1 C23 1.468(3) . ?
N1 C7 1.468(2) . ?
C8 N2 1.355(2) . ?
N2 C17 1.450(2) . ?
N2 C9 1.456(2) . ?
C17 C22 1.382(3) . ?
C17 C18 1.383(3) . ?
C9 C10 1.372(3) . ?
C11 C12 1.404(3) . ?
C11 C16 1.409(3) . ?
C11 C10 1.466(3) . ?
C7 C6 1.522(3) . ?
C21 C20 1.380(3) . ?
C21 C22 1.390(3) . ?
C12 C13 1.391(3) . ?
C16 C15 1.385(3) . ?
C5 C6 1.390(3) . ?
C5 C4 1.394(3) . ?
C13 C14 1.390(3) . ?
C15 C14 1.393(3) . ?
C6 C1 1.396(3) . ?
C4 C3 1.384(3) . ?
C1 C2 1.392(3) . ?
C18 C19 1.389(3) . ?
C3 C2 1.388(3) . ?
C20 C19 1.382(3) . ?
C25 C24 1.386(3) . ?
C25 C26 1.391(3) . ?
C26 C24 1.389(3) 2_666 ?
C24 C26 1.389(3) 2_666 ?
