#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/01/7200178.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_7200178
loop_
_publ_author_name
'Jian, Fangfang'
'Zheng, Jian'
'Li, Yufeng'
'Wang, Jing'
_publ_section_title
;
 Novel ((3Z,5Z)-3,5-bis(phenylimino)-1,2-dithiolan-4-yl) and
 3H-[1,2]dithiolo[3,4-b]quinolin-4(9H)-one heterocycles: an effective
 and facile green route
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              215
_journal_paper_doi               10.1039/b808949c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C22 H13 Cl N2 O S2'
_chemical_formula_weight         420.91
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.64(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.497(2)
_cell_length_b                   7.5370(15)
_cell_length_c                   22.384(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      1.82
_cell_volume                     1884.9(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4160
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0536
_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)+(0.0999P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                2283
_reflns_number_total             3966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808949c.txt
_cod_data_source_block           2e
_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)/c
_cod_database_code               7200178
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 1.04276(8) 0.42210(14) 0.11606(4) 0.0631(3) Uani 1 1 d . . .
S1 S 0.23643(8) 0.22627(14) 0.01827(4) 0.0563(3) Uani 1 1 d . . .
S2 S 0.36716(8) 0.29103(14) 0.09537(4) 0.0550(3) Uani 1 1 d . . .
O1 O 0.5439(2) 0.1769(4) -0.08889(10) 0.0684(8) Uani 1 1 d . . .
N1 N 0.5958(2) 0.3070(4) 0.09315(10) 0.0444(7) Uani 1 1 d . . .
N2 N 0.2948(3) 0.1876(4) -0.09283(12) 0.0526(7) Uani 1 1 d . . .
C1 C 0.6377(3) 0.1593(6) 0.19236(16) 0.0648(11) Uani 1 1 d . . .
H1A H 0.6457 0.0528 0.1728 0.078 Uiso 1 1 calc R . .
C2 C 0.6499(4) 0.1677(8) 0.25567(19) 0.0902(16) Uani 1 1 d . . .
H2B H 0.6683 0.0657 0.2794 0.108 Uiso 1 1 calc R . .
C3 C 0.6348(4) 0.3280(10) 0.28341(18) 0.101(2) Uani 1 1 d . . .
H3A H 0.6403 0.3312 0.3255 0.121 Uiso 1 1 calc R . .
C4 C 0.6118(4) 0.4829(8) 0.24971(19) 0.0898(17) Uani 1 1 d . . .
H4A H 0.6044 0.5896 0.2694 0.108 Uiso 1 1 calc R . .
C5 C 0.5997(3) 0.4795(6) 0.18670(15) 0.0650(11) Uani 1 1 d . . .
H5A H 0.5833 0.5824 0.1633 0.078 Uiso 1 1 calc R . .
C6 C 0.6130(3) 0.3174(5) 0.15960(13) 0.0476(8) Uani 1 1 d . . .
C7 C 0.4841(3) 0.2764(4) 0.05806(14) 0.0441(8) Uani 1 1 d . . .
C8 C 0.4581(3) 0.2381(4) -0.00413(14) 0.0444(8) Uani 1 1 d . . .
C9 C 0.3330(3) 0.2114(4) -0.03503(14) 0.0466(8) Uani 1 1 d . . .
C10 C 0.1743(3) 0.1665(5) -0.12466(15) 0.0504(8) Uani 1 1 d . . .
C11 C 0.0847(3) 0.0851(5) -0.10169(17) 0.0599(10) Uani 1 1 d . . .
H11A H 0.1021 0.0434 -0.0614 0.072 Uiso 1 1 calc R . .
C12 C -0.0289(4) 0.0660(6) -0.1381(2) 0.0717(11) Uani 1 1 d . . .
H12A H -0.0877 0.0113 -0.1223 0.086 Uiso 1 1 calc R . .
C13 C -0.0564(4) 0.1269(6) -0.1976(2) 0.0719(12) Uani 1 1 d . . .
H13A H -0.1338 0.1148 -0.2218 0.086 Uiso 1 1 calc R . .
C14 C 0.0303(4) 0.2057(6) -0.22132(19) 0.0694(11) Uani 1 1 d . . .
H14A H 0.0116 0.2473 -0.2616 0.083 Uiso 1 1 calc R . .
C15 C 0.1456(4) 0.2235(5) -0.18564(17) 0.0638(10) Uani 1 1 d . . .
H15A H 0.2045 0.2739 -0.2025 0.077 Uiso 1 1 calc R . .
C16 C 0.5568(3) 0.2242(5) -0.03489(14) 0.0475(8) Uani 1 1 d . . .
C17 C 0.6766(3) 0.2709(4) 0.00321(13) 0.0440(8) Uani 1 1 d . . .
C18 C 0.6937(3) 0.3124(4) 0.06627(13) 0.0425(8) Uani 1 1 d . . .
C19 C 0.8078(3) 0.3570(5) 0.10077(14) 0.0469(8) Uani 1 1 d . . .
H19A H 0.8198 0.3830 0.1424 0.056 Uiso 1 1 calc R . .
C20 C 0.9020(3) 0.3621(4) 0.07288(14) 0.0471(8) Uani 1 1 d . . .
C21 C 0.8874(3) 0.3197(5) 0.01089(15) 0.0498(8) Uani 1 1 d . . .
H21A H 0.9524 0.3209 -0.0072 0.060 Uiso 1 1 calc R . .
C22 C 0.7754(3) 0.2763(5) -0.02269(14) 0.0492(8) Uani 1 1 d . . .
H22A H 0.7650 0.2495 -0.0642 0.059 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'
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
C9 S1 S2 97.28(12) . . ?
C7 S2 S1 94.38(11) . . ?
C7 N1 C18 120.3(2) . . ?
C7 N1 C6 118.8(2) . . ?
C18 N1 C6 120.6(3) . . ?
C9 N2 C10 126.2(3) . . ?
C2 C1 C6 117.2(4) . . ?
C2 C1 H1A 121.4 . . ?
C6 C1 H1A 121.4 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2B 119.9 . . ?
C1 C2 H2B 119.9 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5A 121.1 . . ?
C6 C5 H5A 121.1 . . ?
C5 C6 C1 123.5(3) . . ?
C5 C6 N1 119.4(3) . . ?
C1 C6 N1 117.0(3) . . ?
N1 C7 C8 124.6(3) . . ?
N1 C7 S2 116.3(2) . . ?
C8 C7 S2 119.1(3) . . ?
C7 C8 C9 117.5(3) . . ?
C7 C8 C16 118.7(3) . . ?
C9 C8 C16 123.8(3) . . ?
N2 C9 C8 124.5(3) . . ?
N2 C9 S1 123.8(3) . . ?
C8 C9 S1 111.6(2) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 N2 116.0(3) . . ?
C11 C10 N2 125.8(3) . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C10 120.6(4) . . ?
C14 C15 H15A 119.7 . . ?
C10 C15 H15A 119.7 . . ?
O1 C16 C8 123.6(3) . . ?
O1 C16 C17 120.9(3) . . ?
C8 C16 C17 115.5(3) . . ?
C22 C17 C18 118.3(3) . . ?
C22 C17 C16 120.4(3) . . ?
C18 C17 C16 121.3(3) . . ?
C19 C18 N1 121.1(3) . . ?
C19 C18 C17 119.8(3) . . ?
N1 C18 C17 119.1(3) . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 Cl1 119.1(3) . . ?
C21 C20 Cl1 119.4(3) . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?
C21 C22 C17 122.2(3) . . ?
C21 C22 H22A 118.9 . . ?
C17 C22 H22A 118.9 . . ?
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
Cl1 C20 1.737(3) . ?
S1 C9 1.815(3) . ?
S1 S2 2.0620(15) . ?
S2 C7 1.745(3) . ?
O1 C16 1.235(4) . ?
N1 C7 1.358(4) . ?
N1 C18 1.397(4) . ?
N1 C6 1.456(3) . ?
N2 C9 1.277(4) . ?
N2 C10 1.409(4) . ?
C1 C2 1.392(5) . ?
C1 C6 1.393(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(8) . ?
C2 H2B 0.9300 . ?
C3 C4 1.382(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5A 0.9300 . ?
C7 C8 1.384(4) . ?
C8 C9 1.455(5) . ?
C8 C16 1.464(4) . ?
C10 C15 1.394(5) . ?
C10 C11 1.397(5) . ?
C11 C12 1.374(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.481(5) . ?
C17 C22 1.393(4) . ?
C17 C18 1.413(4) . ?
C18 C19 1.397(5) . ?
C19 C20 1.373(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.395(4) . ?
C21 C22 1.369(5) . ?
C21 H21A 0.9300 . ?
C22 H22A 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
C9 S1 S2 C7 -2.92(16) . . . . ?
C6 C1 C2 C3 1.5(6) . . . . ?
C1 C2 C3 C4 -2.3(7) . . . . ?
C2 C3 C4 C5 2.0(7) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 N1 177.3(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C1 C6 N1 -177.7(3) . . . . ?
C7 N1 C6 C5 -88.4(4) . . . . ?
C18 N1 C6 C5 97.3(4) . . . . ?
C7 N1 C6 C1 89.1(4) . . . . ?
C18 N1 C6 C1 -85.2(4) . . . . ?
C18 N1 C7 C8 4.2(5) . . . . ?
C6 N1 C7 C8 -170.2(3) . . . . ?
C18 N1 C7 S2 -174.8(2) . . . . ?
C6 N1 C7 S2 10.9(4) . . . . ?
S1 S2 C7 N1 -178.7(2) . . . . ?
S1 S2 C7 C8 2.2(3) . . . . ?
N1 C7 C8 C9 -179.1(3) . . . . ?
S2 C7 C8 C9 -0.1(4) . . . . ?
N1 C7 C8 C16 1.7(5) . . . . ?
S2 C7 C8 C16 -179.3(2) . . . . ?
C10 N2 C9 C8 -178.0(3) . . . . ?
C10 N2 C9 S1 -1.0(5) . . . . ?
C7 C8 C9 N2 174.9(3) . . . . ?
C16 C8 C9 N2 -6.0(5) . . . . ?
C7 C8 C9 S1 -2.5(4) . . . . ?
C16 C8 C9 S1 176.6(3) . . . . ?
S2 S1 C9 N2 -174.0(3) . . . . ?
S2 S1 C9 C8 3.4(2) . . . . ?
C9 N2 C10 C15 151.1(4) . . . . ?
C9 N2 C10 C11 -32.9(6) . . . . ?
C15 C10 C11 C12 -1.5(5) . . . . ?
N2 C10 C11 C12 -177.4(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C10 -1.9(6) . . . . ?
C11 C10 C15 C14 2.5(6) . . . . ?
N2 C10 C15 C14 178.8(3) . . . . ?
C7 C8 C16 O1 174.1(3) . . . . ?
C9 C8 C16 O1 -5.1(5) . . . . ?
C7 C8 C16 C17 -5.8(5) . . . . ?
C9 C8 C16 C17 175.0(3) . . . . ?
O1 C16 C17 C22 5.3(5) . . . . ?
C8 C16 C17 C22 -174.8(3) . . . . ?
O1 C16 C17 C18 -175.3(3) . . . . ?
C8 C16 C17 C18 4.7(5) . . . . ?
C7 N1 C18 C19 175.1(3) . . . . ?
C6 N1 C18 C19 -10.7(5) . . . . ?
C7 N1 C18 C17 -5.3(5) . . . . ?
C6 N1 C18 C17 168.9(3) . . . . ?
C22 C17 C18 C19 -0.2(5) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C22 C17 C18 N1 -179.7(3) . . . . ?
C16 C17 C18 N1 0.8(5) . . . . ?
N1 C18 C19 C20 -179.6(3) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C19 C20 C21 -1.5(5) . . . . ?
C18 C19 C20 Cl1 178.7(2) . . . . ?
C19 C20 C21 C22 1.6(5) . . . . ?
Cl1 C20 C21 C22 -178.7(3) . . . . ?
C20 C21 C22 C17 -0.9(5) . . . . ?
C18 C17 C22 C21 0.2(5) . . . . ?
C16 C17 C22 C21 179.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25946447
