#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024499.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_4024499
loop_
_publ_author_name
'Jing Sun'
'Li-Li Zhang'
'Er-Yan Xia'
'Chao-Guo Yan'
_publ_contact_author_address
;
      College of Chemistry & Chemical Engineering
      Yangzhou University
      Yangzhou 225002, 
      P.R. China
;
_publ_contact_author_email       cgyan@yzu.edu.cn
_publ_contact_author_fax         +86-514-7975590-8401
_publ_contact_author_name        'Chao Guo Yan'
_publ_contact_author_phone       +86-514-7975531
_publ_section_title
;
Synthesis of Dihydrothiophenes or Spirocyclic Compounds by Domino Reactions
of 1,3-Thiazolidinedione
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3398
_journal_page_last               3401
_journal_paper_doi               10.1021/jo900215a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         "'C20 H17 Cl N4 O2 S'"
_chemical_formula_sum            'C20 H17 Cl N4 O2 S'
_chemical_formula_weight         412.89
_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                103.474(8)
_cell_angle_beta                 111.391(6)
_cell_angle_gamma                96.195(8)
_cell_formula_units_Z            2
_cell_length_a                   9.740(5)
_cell_length_b                   10.793(10)
_cell_length_c                   10.943(6)
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1017.7(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8555
_diffrn_reflns_theta_full        27.67
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_correction_T_min  0.9174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         2.117
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.091
_refine_ls_R_factor_all          0.1638
_refine_ls_R_factor_gt           0.1470
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4769
_refine_ls_wR_factor_ref         0.4860
_reflns_number_gt                3537
_reflns_number_total             4584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900215a_si_001_06.cif
_cod_data_source_block           5f
_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_database_code               4024499
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 0.36236(17) 0.60129(17) 0.91247(14) 0.0395(5) Uani 1 1 d . . .
Cl1 Cl 0.2818(4) 1.2370(3) 0.7900(5) 0.1411(19) Uani 1 1 d . . .
C15 C 0.2238(7) 0.8013(6) 0.7060(6) 0.0352(12) Uani 1 1 d . . .
C10 C 0.1754(6) 0.6129(6) 0.7984(6) 0.0337(12) Uani 1 1 d . . .
H10 H 0.1375 0.6790 0.8478 0.040 Uiso 1 1 calc R . .
C9 C 0.0676(7) 0.4798(6) 0.7464(6) 0.0349(12) Uani 1 1 d . . .
C13 C 0.4198(7) 0.5649(6) 0.7741(6) 0.0373(13) Uani 1 1 d . . .
C12 C 0.3263(7) 0.5944(6) 0.6630(6) 0.0351(12) Uani 1 1 d . . .
N1 N -0.1497(6) 0.2551(5) 0.7037(5) 0.0448(13) Uani 1 1 d . . .
C11 C 0.1957(7) 0.6534(6) 0.6790(6) 0.0346(12) Uani 1 1 d . . .
H11 H 0.1041 0.6132 0.5951 0.042 Uiso 1 1 calc R . .
C14 C 0.3388(7) 0.5709(7) 0.5359(7) 0.0415(14) Uani 1 1 d . . .
N3 N 0.5453(7) 0.5201(6) 0.7923(6) 0.0500(15) Uani 1 1 d . . .
H3A H 0.5773 0.5058 0.7278 0.060 Uiso 1 1 calc R . .
H3B H 0.5946 0.5053 0.8686 0.060 Uiso 1 1 calc R . .
N4 N 0.3467(9) 0.5530(8) 0.4310(6) 0.063(2) Uani 1 1 d . . .
N2 N 0.0151(7) 0.4534(6) 0.8385(6) 0.0508(15) Uani 1 1 d . . .
H2B H 0.0599 0.5050 0.9208 0.061 Uiso 1 1 calc R . .
O1 O -0.1539(8) 0.3601(7) 0.9049(6) 0.083(2) Uani 1 1 d . . .
C8 C -0.1023(8) 0.3532(7) 0.8167(7) 0.0493(17) Uani 1 1 d . . .
C7 C -0.2897(8) 0.1576(7) 0.6585(8) 0.0571(19) Uani 1 1 d . . .
H7A H -0.3413 0.1355 0.5594 0.068 Uiso 1 1 calc R . .
H7B H -0.3551 0.1964 0.6979 0.068 Uiso 1 1 calc R . .
C16 C 0.3645(8) 0.8812(8) 0.7765(9) 0.060(2) Uani 1 1 d . . .
H16 H 0.4485 0.8448 0.8063 0.071 Uiso 1 1 calc R . .
C20 C 0.1011(8) 0.8578(7) 0.6586(9) 0.058(2) Uani 1 1 d . . .
H20 H 0.0053 0.8047 0.6084 0.070 Uiso 1 1 calc R . .
C6 C -0.2667(9) 0.0355(8) 0.6967(10) 0.062(2) Uani 1 1 d . . .
C18 C 0.2603(10) 1.0687(8) 0.7569(10) 0.069(2) Uani 1 1 d . . .
C4 C -0.2904(16) -0.1978(12) 0.627(2) 0.139(8) Uani 1 1 d . . .
H4 H -0.3167 -0.2766 0.5585 0.167 Uiso 1 1 calc R . .
C2 C -0.1955(15) -0.0840(14) 0.8629(18) 0.123 Uani 1 1 d . . .
H2 H -0.1556 -0.0852 0.9538 0.147 Uiso 1 1 calc R . .
C17 C 0.3835(10) 1.0161(8) 0.8043(11) 0.075(3) Uani 1 1 d . . .
H17 H 0.4790 1.0697 0.8546 0.090 Uiso 1 1 calc R . .
C19 C 0.1184(11) 0.9916(9) 0.6844(11) 0.077(3) Uani 1 1 d . . .
H19 H 0.0352 1.0285 0.6530 0.092 Uiso 1 1 calc R . .
C5 C -0.3050(12) -0.0827(10) 0.5940(14) 0.091(4) Uani 1 1 d . . .
H5 H -0.3407 -0.0837 0.5024 0.109 Uiso 1 1 calc R . .
C3 C -0.2360(18) -0.1931(17) 0.763(3) 0.170(11) Uani 1 1 d . . .
H3 H -0.2274 -0.2707 0.7856 0.204 Uiso 1 1 calc R . .
C1 C -0.2123(14) 0.0335(13) 0.8333(13) 0.093(4) Uani 1 1 d . . .
H1 H -0.1875 0.1103 0.9039 0.112 Uiso 1 1 calc R . .
O2 O 0.0321(5) 0.4056(4) 0.6324(4) 0.0435(11) Uani 1 1 d . . .
H1A H -0.1227 0.2605 0.6173 0.052 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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
C13 S1 C10 91.5(3) . . ?
C16 C15 C20 118.3(6) . . ?
C16 C15 C11 123.2(6) . . ?
C20 C15 C11 118.5(6) . . ?
C9 C10 C11 111.2(5) . . ?
C9 C10 S1 109.1(4) . . ?
C11 C10 S1 106.4(4) . . ?
C9 C10 H10 110.0 . . ?
C11 C10 H10 110.0 . . ?
S1 C10 H10 110.0 . . ?
O2 C9 N2 123.4(6) . . ?
O2 C9 C10 122.7(5) . . ?
N2 C9 C10 113.9(5) . . ?
N3 C13 C12 129.3(6) . . ?
N3 C13 S1 118.8(5) . . ?
C12 C13 S1 111.8(5) . . ?
C13 C12 C14 124.9(6) . . ?
C13 C12 C11 116.2(5) . . ?
C14 C12 C11 118.9(5) . . ?
C8 N1 C7 121.9(6) . . ?
C8 N1 H1A 122.4 . . ?
C7 N1 H1A 110.7 . . ?
C15 C11 C12 113.5(5) . . ?
C15 C11 C10 112.1(5) . . ?
C12 C11 C10 104.7(5) . . ?
C15 C11 H11 108.8 . . ?
C12 C11 H11 108.8 . . ?
C10 C11 H11 108.8 . . ?
N4 C14 C12 178.6(7) . . ?
C13 N3 H3A 120.0 . . ?
C13 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C9 N2 C8 128.3(5) . . ?
C9 N2 H2B 115.9 . . ?
C8 N2 H2B 115.9 . . ?
O1 C8 N1 123.7(6) . . ?
O1 C8 N2 118.5(6) . . ?
N1 C8 N2 117.8(6) . . ?
N1 C7 C6 114.4(6) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C15 C16 C17 121.0(7) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C19 C20 C15 121.3(7) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C1 C6 C5 118.1(11) . . ?
C1 C6 C7 122.1(9) . . ?
C5 C6 C7 119.8(9) . . ?
C17 C18 C19 121.3(8) . . ?
C17 C18 Cl1 119.9(7) . . ?
C19 C18 Cl1 118.8(7) . . ?
C3 C4 C5 118.3(16) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C3 C2 C1 120.2(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C18 C17 C16 119.2(8) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C18 C19 C20 118.9(8) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C4 C5 C6 120.7(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C2 C3 C4 122.9(13) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C2 C1 C6 119.6(14) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
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 C13 1.775(6) . ?
S1 C10 1.831(6) . ?
Cl1 C18 1.741(8) . ?
C15 C16 1.372(10) . ?
C15 C20 1.386(9) . ?
C15 C11 1.529(8) . ?
C10 C9 1.532(8) . ?
C10 C11 1.541(8) . ?
C10 H10 0.9800 . ?
C9 O2 1.216(7) . ?
C9 N2 1.354(8) . ?
C13 N3 1.328(8) . ?
C13 C12 1.358(8) . ?
C12 C14 1.406(8) . ?
C12 C11 1.529(8) . ?
N1 C8 1.316(8) . ?
N1 C7 1.473(9) . ?
N1 H1A 1.0813 . ?
C11 H11 0.9800 . ?
C14 N4 1.152(8) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N2 C8 1.396(8) . ?
N2 H2B 0.8600 . ?
O1 C8 1.231(8) . ?
C7 C6 1.488(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 C17 1.393(11) . ?
C16 H16 0.9300 . ?
C20 C19 1.385(12) . ?
C20 H20 0.9300 . ?
C6 C1 1.397(15) . ?
C6 C5 1.398(13) . ?
C18 C17 1.364(12) . ?
C18 C19 1.370(13) . ?
C4 C3 1.37(3) . ?
C4 C5 1.379(19) . ?
C4 H4 0.9300 . ?
C2 C3 1.31(3) . ?
C2 C1 1.393(16) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
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
C13 S1 C10 C9 92.7(4) . . . . ?
C13 S1 C10 C11 -27.3(4) . . . . ?
C11 C10 C9 O2 15.4(8) . . . . ?
S1 C10 C9 O2 -101.7(6) . . . . ?
C11 C10 C9 N2 -164.2(5) . . . . ?
S1 C10 C9 N2 78.8(6) . . . . ?
C10 S1 C13 N3 -166.9(6) . . . . ?
C10 S1 C13 C12 15.9(5) . . . . ?
N3 C13 C12 C14 6.1(12) . . . . ?
S1 C13 C12 C14 -176.9(5) . . . . ?
N3 C13 C12 C11 -175.9(7) . . . . ?
S1 C13 C12 C11 1.0(7) . . . . ?
C16 C15 C11 C12 -31.7(9) . . . . ?
C20 C15 C11 C12 149.2(6) . . . . ?
C16 C15 C11 C10 86.7(8) . . . . ?
C20 C15 C11 C10 -92.5(7) . . . . ?
C13 C12 C11 C15 101.2(6) . . . . ?
C14 C12 C11 C15 -80.8(7) . . . . ?
C13 C12 C11 C10 -21.3(7) . . . . ?
C14 C12 C11 C10 156.8(6) . . . . ?
C9 C10 C11 C15 148.5(5) . . . . ?
S1 C10 C11 C15 -92.8(5) . . . . ?
C9 C10 C11 C12 -88.1(5) . . . . ?
S1 C10 C11 C12 30.6(5) . . . . ?
C13 C12 C14 N4 -172(35) . . . . ?
C11 C12 C14 N4 10(36) . . . . ?
O2 C9 N2 C8 -11.5(12) . . . . ?
C10 C9 N2 C8 168.1(7) . . . . ?
C7 N1 C8 O1 12.9(13) . . . . ?
C7 N1 C8 N2 -168.5(7) . . . . ?
C9 N2 C8 O1 -165.4(8) . . . . ?
C9 N2 C8 N1 15.9(13) . . . . ?
C8 N1 C7 C6 -97.6(9) . . . . ?
C20 C15 C16 C17 2.3(13) . . . . ?
C11 C15 C16 C17 -176.9(8) . . . . ?
C16 C15 C20 C19 -1.8(13) . . . . ?
C11 C15 C20 C19 177.5(9) . . . . ?
N1 C7 C6 C1 66.6(12) . . . . ?
N1 C7 C6 C5 -115.7(9) . . . . ?
C19 C18 C17 C16 1.0(17) . . . . ?
Cl1 C18 C17 C16 -179.8(9) . . . . ?
C15 C16 C17 C18 -2.0(15) . . . . ?
C17 C18 C19 C20 -0.4(18) . . . . ?
Cl1 C18 C19 C20 -179.7(9) . . . . ?
C15 C20 C19 C18 0.8(17) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C1 C6 C5 C4 0.5(16) . . . . ?
C7 C6 C5 C4 -177.3(10) . . . . ?
C1 C2 C3 C4 3(3) . . . . ?
C5 C4 C3 C2 -1(3) . . . . ?
C3 C2 C1 C6 -3(2) . . . . ?
C5 C6 C1 C2 1.1(17) . . . . ?
C7 C6 C1 C2 178.8(10) . . . . ?
