#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024497.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_4024497
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         'C17 H17 F N4 O2 S, C3 H6 N O'
_chemical_formula_sum            'C20 H23 F N5 O3 S'
_chemical_formula_weight         432.49
_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                66.5450(10)
_cell_angle_beta                 81.0860(10)
_cell_angle_gamma                87.7400(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5865(7)
_cell_length_b                   12.5670(13)
_cell_length_c                   14.6548(15)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      2.8
_cell_volume                     1099.0(2)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8255
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0405
_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)+(0.0644P)²+0.5031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                3711
_reflns_number_total             4041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900215a_si_001_04.cif
_cod_data_source_block           3g
_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               4024497
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 0.60667(6) 0.14240(4) 0.20882(3) 0.02349(13) Uani 1 1 d . . .
O2 O 0.50672(19) 0.23334(11) 0.01403(9) 0.0301(3) Uani 1 1 d . . .
O1 O 1.03169(19) 0.04865(11) 0.08310(9) 0.0319(3) Uani 1 1 d . . .
N3 N 0.7693(2) 0.11275(12) -0.00452(10) 0.0253(3) Uani 1 1 d . . .
H3 H 0.8065 0.0661 -0.0336 0.030 Uiso 1 1 calc R . .
N2 N 0.6611(2) 0.00208(14) 0.39641(10) 0.0287(3) Uani 1 1 d . . .
C17 C 1.0973(2) 0.05892(16) 0.34668(12) 0.0271(4) Uani 1 1 d . . .
C9 C 0.7550(2) 0.07584(14) 0.30577(11) 0.0214(3) Uani 1 1 d . . .
N4 N 0.5297(2) 0.17434(13) -0.11419(11) 0.0270(3) Uani 1 1 d . . .
N1 N 1.2076(2) 0.01641(17) 0.40453(12) 0.0423(4) Uani 1 1 d . . .
C11 C 0.8872(2) 0.11435(14) 0.06411(11) 0.0226(3) Uani 1 1 d . . .
C12 C 0.5939(2) 0.17847(14) -0.03327(12) 0.0244(3) Uani 1 1 d . . .
C7 C 1.0161(2) 0.20236(13) 0.17403(12) 0.022 Uani 1 1 d . . .
H7 H 1.1454 0.1827 0.1419 0.026 Uiso 1 1 calc R . .
C10 C 0.8404(2) 0.19798(14) 0.11602(11) 0.0214(3) Uani 1 1 d . . .
H10 H 0.8177 0.2758 0.0666 0.026 Uiso 1 1 calc R . .
C6 C 1.0414(3) 0.32144(14) 0.17615(13) 0.0261(3) Uani 1 1 d . . .
C8 C 0.9580(2) 0.10755(14) 0.27806(12) 0.021 Uani 1 1 d . . .
F1 F 1.1224(2) 0.63997(11) 0.18625(12) 0.0617(4) Uani 1 1 d . . .
C5 C 1.2020(3) 0.39556(15) 0.11402(13) 0.0308(4) Uani 1 1 d . . .
H5 H 1.2922 0.3729 0.0699 0.037 Uiso 1 1 calc R . .
C13 C 0.3501(3) 0.24149(18) -0.15162(14) 0.0361(4) Uani 1 1 d . . .
H13A H 0.3752 0.3239 -0.1721 0.043 Uiso 1 1 calc R . .
H13B H 0.2287 0.2171 -0.1008 0.043 Uiso 1 1 calc R . .
C16 C 0.6448(3) 0.13229(17) -0.18789(14) 0.0330(4) Uani 1 1 d . . .
H16A H 0.6267 0.0490 -0.1656 0.040 Uiso 1 1 calc R . .
H16B H 0.7903 0.1514 -0.1993 0.040 Uiso 1 1 calc R . .
C4 C 1.2304(3) 0.50372(16) 0.11668(16) 0.0389(4) Uani 1 1 d . . .
H4 H 1.3384 0.5534 0.0751 0.047 Uiso 1 1 calc R . .
C14 C 0.3267(3) 0.21316(19) -0.24138(16) 0.0425(5) Uani 1 1 d . . .
H14A H 0.2449 0.1426 -0.2205 0.051 Uiso 1 1 calc R . .
H14B H 0.2634 0.2762 -0.2912 0.051 Uiso 1 1 calc R . .
C3 C 1.0951(3) 0.53473(16) 0.18210(17) 0.0415(5) Uani 1 1 d . . .
C15 C 0.5477(3) 0.19753(19) -0.28232(15) 0.0420(5) Uani 1 1 d . . .
H15A H 0.6169 0.2720 -0.3223 0.050 Uiso 1 1 calc R . .
H15B H 0.5527 0.1527 -0.3233 0.050 Uiso 1 1 calc R . .
C1 C 0.9082(3) 0.35742(19) 0.24136(19) 0.0497(6) Uani 1 1 d . . .
H1 H 0.7999 0.3084 0.2836 0.060 Uiso 1 1 calc R . .
C2 C 0.9337(4) 0.4650(2) 0.2447(2) 0.0565(7) Uani 1 1 d . . .
H2 H 0.8439 0.4888 0.2881 0.068 Uiso 1 1 calc R . .
N5 N 0.2521(3) 0.34929(17) 0.45527(14) 0.0496(5) Uani 1 1 d . . .
C18 C 0.3611(5) 0.3016(3) 0.3889(2) 0.0771(9) Uani 1 1 d . . .
H18A H 0.4416 0.3618 0.3335 0.116 Uiso 1 1 calc R . .
H18B H 0.2649 0.2685 0.3639 0.116 Uiso 1 1 calc R . .
H18C H 0.4501 0.2424 0.4245 0.116 Uiso 1 1 calc R . .
C20 C 0.0640(5) 0.2918(3) 0.5161(2) 0.0799(9) Uani 1 1 d . . .
H20A H 0.0945 0.2186 0.5665 0.120 Uiso 1 1 calc R . .
H20B H -0.0227 0.2789 0.4744 0.120 Uiso 1 1 calc R . .
H20C H -0.0054 0.3394 0.5481 0.120 Uiso 1 1 calc R . .
C19 C 0.3210(6) 0.4441(3) 0.4594(4) 0.0983(13) Uani 1 1 d . . .
O3' O 0.2170(7) 0.4695(4) 0.5392(3) 0.0802(12) Uani 0.50 1 d P . .
H2A H 0.5332 -0.0100 0.4106 0.037(6) Uiso 1 1 d R . .
H2B H 0.7195 -0.0141 0.4507 0.041(6) Uiso 1 1 d R . .
O3 O 0.4911(7) 0.5041(4) 0.3800(4) 0.0922(15) Uani 0.50 1 d P . .
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'
F F 0.0171 0.0103 '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 C10 90.99(7) . . ?
C11 N3 C12 127.75(14) . . ?
C11 N3 H3 116.1 . . ?
C12 N3 H3 116.1 . . ?
C9 N2 H2A 123.3 . . ?
C9 N2 H2B 120.2 . . ?
H2A N2 H2B 112.1 . . ?
N1 C17 C8 178.05(19) . . ?
N2 C9 C8 127.57(14) . . ?
N2 C9 S1 118.79(12) . . ?
C8 C9 S1 113.64(12) . . ?
C12 N4 C13 119.20(15) . . ?
C12 N4 C16 127.19(14) . . ?
C13 N4 C16 111.95(14) . . ?
O1 C11 N3 119.70(14) . . ?
O1 C11 C10 120.07(14) . . ?
N3 C11 C10 120.23(14) . . ?
O2 C12 N4 123.32(15) . . ?
O2 C12 N3 121.88(15) . . ?
N4 C12 N3 114.79(14) . . ?
C8 C7 C6 112.88(13) . . ?
C8 C7 C10 104.40(12) . . ?
C6 C7 C10 112.45(13) . . ?
C8 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C10 C7 H7 109.0 . . ?
C11 C10 C7 111.42(13) . . ?
C11 C10 S1 107.25(11) . . ?
C7 C10 S1 107.60(10) . . ?
C11 C10 H10 110.2 . . ?
C7 C10 H10 110.2 . . ?
S1 C10 H10 110.2 . . ?
C5 C6 C1 118.46(16) . . ?
C5 C6 C7 120.14(15) . . ?
C1 C6 C7 121.39(15) . . ?
C9 C8 C17 120.25(14) . . ?
C9 C8 C7 115.83(14) . . ?
C17 C8 C7 123.77(14) . . ?
C6 C5 C4 120.91(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N4 C13 C14 103.03(15) . . ?
N4 C13 H13A 111.2 . . ?
C14 C13 H13A 111.2 . . ?
N4 C13 H13B 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
N4 C16 C15 102.73(15) . . ?
N4 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
N4 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C3 C4 C5 118.22(17) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C15 C14 C13 102.97(16) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
F1 C3 C2 118.06(18) . . ?
F1 C3 C4 118.81(18) . . ?
C2 C3 C4 123.13(18) . . ?
C14 C15 C16 103.71(16) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C2 C1 C6 121.37(18) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 117.92(19) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C19 N5 C18 120.8(3) . . ?
C19 N5 C20 121.3(3) . . ?
C18 N5 C20 118.0(2) . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C20 H20A 109.5 . . ?
N5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C19 O3' 114.0(4) . . ?
N5 C19 O3 114.4(3) . . ?
O3' C19 O3 131.6(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 C9 1.7585(16) . ?
S1 C10 1.8403(16) . ?
O2 C12 1.230(2) . ?
O1 C11 1.226(2) . ?
N3 C11 1.369(2) . ?
N3 C12 1.411(2) . ?
N3 H3 0.8600 . ?
N2 C9 1.348(2) . ?
N2 H2A 0.8408 . ?
N2 H2B 0.8841 . ?
C17 N1 1.154(2) . ?
C17 C8 1.407(2) . ?
C9 C8 1.362(2) . ?
N4 C12 1.339(2) . ?
N4 C13 1.472(2) . ?
N4 C16 1.480(2) . ?
C11 C10 1.522(2) . ?
C7 C8 1.516(2) . ?
C7 C6 1.525(2) . ?
C7 C10 1.553(2) . ?
C7 H7 0.9800 . ?
C10 H10 0.9800 . ?
C6 C5 1.386(2) . ?
C6 C1 1.393(3) . ?
F1 C3 1.368(2) . ?
C5 C4 1.396(3) . ?
C5 H5 0.9300 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 C15 1.525(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C4 C3 1.368(3) . ?
C4 H4 0.9300 . ?
C14 C15 1.522(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C3 C2 1.367(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 C2 1.389(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
N5 C19 1.318(4) . ?
N5 C18 1.427(3) . ?
N5 C20 1.438(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 O3' 1.404(5) . ?
C19 O3 1.464(6) . ?
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
C10 S1 C9 N2 -170.00(14) . . . . ?
C10 S1 C9 C8 10.27(13) . . . . ?
C12 N3 C11 O1 177.60(15) . . . . ?
C12 N3 C11 C10 -2.9(2) . . . . ?
C13 N4 C12 O2 2.2(3) . . . . ?
C16 N4 C12 O2 166.27(16) . . . . ?
C13 N4 C12 N3 -178.92(15) . . . . ?
C16 N4 C12 N3 -14.8(2) . . . . ?
C11 N3 C12 O2 -12.0(3) . . . . ?
C11 N3 C12 N4 169.05(15) . . . . ?
O1 C11 C10 C7 10.6(2) . . . . ?
N3 C11 C10 C7 -168.84(14) . . . . ?
O1 C11 C10 S1 -106.87(15) . . . . ?
N3 C11 C10 S1 73.66(16) . . . . ?
C8 C7 C10 C11 -89.27(14) . . . . ?
C6 C7 C10 C11 148.02(13) . . . . ?
C8 C7 C10 S1 28.03(14) . . . . ?
C6 C7 C10 S1 -94.68(13) . . . . ?
C9 S1 C10 C11 97.33(11) . . . . ?
C9 S1 C10 C7 -22.65(11) . . . . ?
C8 C7 C6 C5 138.57(16) . . . . ?
C10 C7 C6 C5 -103.63(18) . . . . ?
C8 C7 C6 C1 -40.0(2) . . . . ?
C10 C7 C6 C1 77.8(2) . . . . ?
N2 C9 C8 C17 2.2(3) . . . . ?
S1 C9 C8 C17 -178.15(12) . . . . ?
N2 C9 C8 C7 -173.60(15) . . . . ?
S1 C9 C8 C7 6.10(18) . . . . ?
N1 C17 C8 C9 21(6) . . . . ?
N1 C17 C8 C7 -164(6) . . . . ?
C6 C7 C8 C9 99.85(16) . . . . ?
C10 C7 C8 C9 -22.57(18) . . . . ?
C6 C7 C8 C17 -75.73(19) . . . . ?
C10 C7 C8 C17 161.84(15) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C7 C6 C5 C4 -178.46(17) . . . . ?
C12 N4 C13 C14 -179.48(16) . . . . ?
C16 N4 C13 C14 14.1(2) . . . . ?
C12 N4 C16 C15 -154.65(17) . . . . ?
C13 N4 C16 C15 10.4(2) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
N4 C13 C14 C15 -32.9(2) . . . . ?
C5 C4 C3 F1 179.29(19) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C13 C14 C15 C16 40.0(2) . . . . ?
N4 C16 C15 C14 -30.82(19) . . . . ?
C5 C6 C1 C2 0.1(4) . . . . ?
C7 C6 C1 C2 178.7(2) . . . . ?
F1 C3 C2 C1 -179.1(2) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C18 N5 C19 O3' -170.1(3) . . . . ?
C20 N5 C19 O3' 10.8(5) . . . . ?
C18 N5 C19 O3 10.2(5) . . . . ?
C20 N5 C19 O3 -168.9(3) . . . . ?
