#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024903.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_4024903
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 H22 N3 O2 S2'
_chemical_formula_weight         472.59
_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                91.851(2)
_cell_angle_beta                 102.120(2)
_cell_angle_gamma                102.469(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5042(2)
_cell_length_b                   10.2182(3)
_cell_length_c                   12.0526(4)
_cell_measurement_reflns_used    16303
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1113.71(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, 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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22645
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9607
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0687P)²+0.2090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                4034
_reflns_number_total             5094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900960a_si_003.cif
_cod_data_source_block           2007acc0620
_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               4024903
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 0.46168(5) 0.40031(4) 0.64751(4) 0.01773(13) Uani 1 1 d . . .
S2 S 0.74610(5) 0.28188(5) 0.44971(4) 0.02336(14) Uani 1 1 d . . .
N1 N 0.46157(15) 0.26245(14) 0.46817(12) 0.0159(3) Uani 1 1 d . . .
N2 N 0.21979(15) 0.25653(15) 0.50562(12) 0.0185(3) Uani 1 1 d . . .
N3 N 0.32314(18) -0.13660(16) 0.10432(13) 0.0250(4) Uani 1 1 d . . .
O1 O 0.24807(18) -0.24751(14) 0.11541(13) 0.0384(4) Uani 1 1 d . . .
O2 O 0.36796(18) -0.10688(15) 0.01821(12) 0.0358(4) Uani 1 1 d . . .
C1 C 0.37107(19) 0.02739(18) 0.39375(15) 0.0184(4) Uani 1 1 d . . .
H1 H 0.3602 0.0039 0.4676 0.022 Uiso 1 1 calc R . .
C2 C 0.33645(19) -0.07136(18) 0.30422(16) 0.0198(4) Uani 1 1 d . . .
H2 H 0.2988 -0.1629 0.3149 0.024 Uiso 1 1 calc R . .
C3 C 0.35831(19) -0.03259(18) 0.19925(15) 0.0194(4) Uani 1 1 d . . .
C4 C 0.4096(2) 0.09981(18) 0.17853(15) 0.0211(4) Uani 1 1 d . . .
H4 H 0.4231 0.1227 0.1051 0.025 Uiso 1 1 calc R . .
C5 C 0.4406(2) 0.19802(18) 0.26772(15) 0.0203(4) Uani 1 1 d . . .
H5 H 0.4744 0.2899 0.2560 0.024 Uiso 1 1 calc R . .
C6 C 0.42175(18) 0.16080(17) 0.37440(15) 0.0170(4) Uani 1 1 d . . .
C7 C 0.61766(18) 0.32413(17) 0.51497(15) 0.0165(3) Uani 1 1 d . . .
C8 C 0.63303(18) 0.40368(17) 0.61268(14) 0.0162(4) Uani 1 1 d . . .
C9 C 0.36751(18) 0.29467(17) 0.52843(14) 0.0165(3) Uani 1 1 d . . .
C10 C 0.76562(18) 0.48045(17) 0.69402(14) 0.0166(4) Uani 1 1 d . . .
C11 C 0.90528(19) 0.50999(18) 0.66756(15) 0.0197(4) Uani 1 1 d . . .
H11 H 0.9154 0.4827 0.5941 0.024 Uiso 1 1 calc R . .
C12 C 1.02973(19) 0.57913(18) 0.74814(16) 0.0220(4) Uani 1 1 d . . .
H12 H 1.1238 0.5977 0.7291 0.026 Uiso 1 1 calc R . .
C13 C 1.0172(2) 0.62075(19) 0.85542(16) 0.0254(4) Uani 1 1 d . . .
H13 H 1.1022 0.6668 0.9103 0.030 Uiso 1 1 calc R . .
C14 C 0.8791(2) 0.5944(2) 0.88192(16) 0.0261(4) Uani 1 1 d . . .
H14 H 0.8695 0.6236 0.9550 0.031 Uiso 1 1 calc R . .
C15 C 0.7551(2) 0.52599(19) 0.80260(15) 0.0215(4) Uani 1 1 d . . .
H15 H 0.6614 0.5095 0.8220 0.026 Uiso 1 1 calc R . .
C16 C 0.1250(2) 0.18034(19) 0.40091(16) 0.0235(4) Uani 1 1 d . . .
H16A H 0.1681 0.2074 0.3358 0.035 Uiso 1 1 calc R . .
H16B H 0.0263 0.1989 0.3894 0.035 Uiso 1 1 calc R . .
H16C H 0.1176 0.0839 0.4078 0.035 Uiso 1 1 calc R . .
C17 C 0.14405(19) 0.28824(19) 0.59389(15) 0.0211(4) Uani 1 1 d . . .
H17A H 0.0416 0.2915 0.5570 0.025 Uiso 1 1 calc R . .
H17B H 0.1947 0.3788 0.6311 0.025 Uiso 1 1 calc R . .
C18 C 0.13869(18) 0.18848(18) 0.68498(15) 0.0202(4) Uani 1 1 d . . .
C19 C 0.2118(2) 0.08350(19) 0.69089(16) 0.0237(4) Uani 1 1 d . . .
H19 H 0.2686 0.0724 0.6366 0.028 Uiso 1 1 calc R . .
C20 C 0.2023(2) -0.0048(2) 0.77557(17) 0.0282(4) Uani 1 1 d . . .
H20 H 0.2528 -0.0759 0.7791 0.034 Uiso 1 1 calc R . .
C21 C 0.1196(2) 0.0104(2) 0.85467(17) 0.0306(5) Uani 1 1 d . . .
H21 H 0.1125 -0.0506 0.9122 0.037 Uiso 1 1 calc R . .
C22 C 0.0468(2) 0.1148(2) 0.84989(17) 0.0308(5) Uani 1 1 d . . .
H22 H -0.0090 0.1260 0.9049 0.037 Uiso 1 1 calc R . .
C23 C 0.0552(2) 0.2028(2) 0.76501(16) 0.0251(4) Uani 1 1 d . . .
H23 H 0.0039 0.2732 0.7614 0.030 Uiso 1 1 calc R . .
C25 C 0.4307(2) 0.59920(19) 0.95495(16) 0.0254(4) Uani 1 1 d . . .
H25 H 0.3832 0.6670 0.9241 0.030 Uiso 1 1 calc R . .
C26 C 0.5617(2) 0.63435(19) 1.03909(16) 0.0252(4) Uani 1 1 d . . .
H26 H 0.6035 0.7259 1.0656 0.030 Uiso 1 1 calc R . .
C24 C 0.3705(2) 0.4654(2) 0.91674(16) 0.0252(4) Uani 1 1 d . . .
H24 H 0.2816 0.4419 0.8596 0.030 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
C9 S1 C8 92.02(8) . . ?
C9 N1 C6 125.07(14) . . ?
C9 N1 C7 115.01(14) . . ?
C6 N1 C7 119.30(13) . . ?
C9 N2 C17 117.83(15) . . ?
C9 N2 C16 125.92(15) . . ?
C17 N2 C16 116.20(14) . . ?
O2 N3 O1 124.01(16) . . ?
O2 N3 C3 118.08(16) . . ?
O1 N3 C3 117.90(16) . . ?
C2 C1 C6 119.43(16) . . ?
C3 C2 C1 118.08(16) . . ?
C2 C3 C4 123.27(16) . . ?
C2 C3 N3 118.42(16) . . ?
C4 C3 N3 118.30(16) . . ?
C3 C4 C5 118.24(17) . . ?
C4 C5 C6 119.36(16) . . ?
C5 C6 C1 121.60(16) . . ?
C5 C6 N1 119.10(15) . . ?
C1 C6 N1 119.25(15) . . ?
C8 C7 N1 110.12(14) . . ?
C8 C7 S2 131.19(13) . . ?
N1 C7 S2 118.57(12) . . ?
C7 C8 C10 131.26(15) . . ?
C7 C8 S1 111.78(13) . . ?
C10 C8 S1 116.80(12) . . ?
N2 C9 N1 128.57(16) . . ?
N2 C9 S1 120.37(13) . . ?
N1 C9 S1 111.05(12) . . ?
C11 C10 C15 117.69(16) . . ?
C11 C10 C8 122.18(16) . . ?
C15 C10 C8 120.14(15) . . ?
C12 C11 C10 120.69(17) . . ?
C13 C12 C11 120.60(17) . . ?
C12 C13 C14 119.26(18) . . ?
C15 C14 C13 120.54(18) . . ?
C14 C15 C10 121.19(17) . . ?
N2 C17 C18 114.30(14) . . ?
C23 C18 C19 118.94(17) . . ?
C23 C18 C17 118.01(16) . . ?
C19 C18 C17 123.04(16) . . ?
C20 C19 C18 120.49(18) . . ?
C21 C20 C19 120.14(19) . . ?
C20 C21 C22 119.88(19) . . ?
C23 C22 C21 120.17(18) . . ?
C22 C23 C18 120.38(18) . . ?
C24 C25 C26 119.89(18) . . ?
C24 C26 C25 119.42(18) 2_667 . ?
C26 C24 C25 120.69(18) 2_667 . ?
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 C9 1.7233(18) . ?
S1 C8 1.7588(16) . ?
S2 C7 1.7042(17) . ?
N1 C9 1.349(2) . ?
N1 C6 1.440(2) . ?
N1 C7 1.462(2) . ?
N2 C9 1.339(2) . ?
N2 C17 1.468(2) . ?
N2 C16 1.472(2) . ?
N3 O2 1.225(2) . ?
N3 O1 1.230(2) . ?
N3 C3 1.469(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.389(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.389(2) . ?
C7 C8 1.372(2) . ?
C8 C10 1.473(2) . ?
C10 C11 1.402(2) . ?
C10 C15 1.405(2) . ?
C11 C12 1.398(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.385(3) . ?
C17 C18 1.523(3) . ?
C18 C23 1.394(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.388(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.387(3) . ?
C25 C24 1.385(3) . ?
C25 C26 1.400(3) . ?
C26 C24 1.383(3) 2_667 ?
C24 C26 1.383(3) 2_667 ?
