#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/01/7200179.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_7200179
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 H14 Cl2 N2 O S2'
_chemical_formula_weight         457.37
_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                87.60(3)
_cell_angle_beta                 85.58(3)
_cell_angle_gamma                78.10(3)
_cell_formula_units_Z            2
_cell_length_a                   10.084(2)
_cell_length_b                   10.331(2)
_cell_length_c                   10.414(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      1.96
_cell_volume                     1058.1(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4872
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0668
_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)+(0.1044P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.2053
_reflns_number_gt                2192
_reflns_number_total             4604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808949c.txt
_cod_data_source_block           1e
_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               7200179
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
Cl1 Cl -0.30253(16) 0.1448(2) 0.95117(15) 0.0904(6) Uani 1 1 d . . .
Cl2 Cl 0.28010(14) 0.10702(15) 0.69545(15) 0.0716(5) Uani 1 1 d . . .
S1 S 0.34108(15) 0.47932(15) 0.93360(13) 0.0667(5) Uani 1 1 d . . .
S2 S 0.33233(14) 0.59898(14) 0.76873(13) 0.0625(5) Uani 1 1 d . . .
O1 O 0.0151(3) 0.4067(4) 0.6122(3) 0.0620(10) Uani 1 1 d . . .
N1 N 0.1741(4) 0.5798(4) 0.5868(3) 0.0511(10) Uani 1 1 d . . .
H1A H 0.1084 0.5537 0.5545 0.061 Uiso 1 1 calc R . .
N2 N 0.1750(4) 0.3085(4) 0.9763(3) 0.0487(10) Uani 1 1 d . . .
C1 C 0.1723(7) 0.8063(6) 0.5168(5) 0.0723(17) Uani 1 1 d . . .
H1B H 0.0896 0.8337 0.5636 0.087 Uiso 1 1 calc R . .
C2 C 0.2373(8) 0.8981(6) 0.4451(6) 0.085(2) Uani 1 1 d . . .
H2B H 0.1976 0.9877 0.4458 0.102 Uiso 1 1 calc R . .
C3 C 0.3567(8) 0.8566(8) 0.3755(6) 0.090(2) Uani 1 1 d . . .
H3A H 0.3988 0.9180 0.3297 0.108 Uiso 1 1 calc R . .
C4 C 0.4144(7) 0.7280(8) 0.3724(6) 0.087(2) Uani 1 1 d . . .
H4A H 0.4954 0.7007 0.3228 0.105 Uiso 1 1 calc R . .
C5 C 0.3551(6) 0.6346(6) 0.4420(6) 0.0713(16) Uani 1 1 d . . .
H5A H 0.3957 0.5453 0.4394 0.086 Uiso 1 1 calc R . .
C6 C 0.2358(5) 0.6762(5) 0.5146(4) 0.0466(12) Uani 1 1 d . . .
C7 C 0.2121(4) 0.5286(5) 0.7000(4) 0.0438(11) Uani 1 1 d . . .
C8 C 0.1633(4) 0.4270(4) 0.7693(4) 0.0378(10) Uani 1 1 d . . .
C9 C 0.2128(4) 0.3914(4) 0.8953(4) 0.0403(10) Uani 1 1 d . . .
C10 C 0.2389(5) 0.2802(4) 1.0937(4) 0.0422(11) Uani 1 1 d . . .
C11 C 0.3679(5) 0.2073(5) 1.0963(5) 0.0608(14) Uani 1 1 d . . .
H11A H 0.4153 0.1750 1.0202 0.073 Uiso 1 1 calc R . .
C12 C 0.4283(6) 0.1813(6) 1.2117(6) 0.0734(18) Uani 1 1 d . . .
H12A H 0.5170 0.1331 1.2118 0.088 Uiso 1 1 calc R . .
C13 C 0.3623(7) 0.2236(6) 1.3230(6) 0.0781(19) Uani 1 1 d . . .
H13A H 0.4050 0.2067 1.3998 0.094 Uiso 1 1 calc R . .
C14 C 0.2294(8) 0.2931(7) 1.3224(5) 0.086(2) Uani 1 1 d . . .
H14A H 0.1814 0.3205 1.3996 0.103 Uiso 1 1 calc R . .
C15 C 0.1675(6) 0.3220(5) 1.2080(5) 0.0633(14) Uani 1 1 d . . .
H15A H 0.0784 0.3692 1.2080 0.076 Uiso 1 1 calc R . .
C16 C 0.0680(4) 0.3642(4) 0.7125(4) 0.0410(11) Uani 1 1 d . . .
C17 C 0.0301(4) 0.2397(4) 0.7720(4) 0.0369(10) Uani 1 1 d . . .
C18 C 0.1146(5) 0.1182(5) 0.7624(4) 0.0456(11) Uani 1 1 d . . .
C19 C 0.0718(6) 0.0034(5) 0.8050(5) 0.0620(14) Uani 1 1 d . . .
H19A H 0.1302 -0.0785 0.7957 0.074 Uiso 1 1 calc R . .
C20 C -0.0583(6) 0.0119(6) 0.8612(5) 0.0664(16) Uani 1 1 d . . .
H20A H -0.0885 -0.0640 0.8904 0.080 Uiso 1 1 calc R . .
C21 C -0.1411(5) 0.1324(6) 0.8732(4) 0.0547(13) Uani 1 1 d . . .
C22 C -0.1005(5) 0.2474(5) 0.8275(4) 0.0483(12) Uani 1 1 d . . .
H22A H -0.1603 0.3288 0.8342 0.058 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 96.45(15) . . ?
C7 S2 S1 95.10(16) . . ?
C7 N1 C6 124.0(4) . . ?
C7 N1 H1A 118.0 . . ?
C6 N1 H1A 118.0 . . ?
C9 N2 C10 119.8(4) . . ?
C6 C1 C2 117.5(6) . . ?
C6 C1 H1B 121.3 . . ?
C2 C1 H1B 121.3 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2B 119.7 . . ?
C1 C2 H2B 119.7 . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 121.0(7) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 118.9(6) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C1 C6 C5 121.5(5) . . ?
C1 C6 N1 119.3(5) . . ?
C5 C6 N1 119.1(5) . . ?
N1 C7 C8 126.3(4) . . ?
N1 C7 S2 115.7(3) . . ?
C8 C7 S2 118.0(3) . . ?
C7 C8 C9 117.2(4) . . ?
C7 C8 C16 119.0(4) . . ?
C9 C8 C16 123.7(4) . . ?
N2 C9 C8 127.0(4) . . ?
N2 C9 S1 120.0(3) . . ?
C8 C9 S1 113.0(3) . . ?
C11 C10 C15 119.3(4) . . ?
C11 C10 N2 121.1(4) . . ?
C15 C10 N2 119.6(4) . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 121.6(6) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C14 118.9(5) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C15 C14 C13 120.6(6) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C10 C15 C14 119.5(5) . . ?
C10 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
O1 C16 C8 122.3(4) . . ?
O1 C16 C17 116.4(4) . . ?
C8 C16 C17 121.3(4) . . ?
C18 C17 C22 118.7(4) . . ?
C18 C17 C16 122.7(4) . . ?
C22 C17 C16 118.3(4) . . ?
C17 C18 C19 121.6(5) . . ?
C17 C18 Cl2 119.3(3) . . ?
C19 C18 Cl2 119.1(4) . . ?
C20 C19 C18 119.4(5) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C21 C20 C19 119.0(5) . . ?
C21 C20 H20A 120.5 . . ?
C19 C20 H20A 120.5 . . ?
C20 C21 C22 121.9(5) . . ?
C20 C21 Cl1 119.3(4) . . ?
C22 C21 Cl1 118.8(5) . . ?
C17 C22 C21 119.3(5) . . ?
C17 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
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
Cl1 C21 1.745(5) . ?
Cl2 C18 1.742(5) . ?
S1 C9 1.804(4) . ?
S1 S2 2.0699(19) . ?
S2 C7 1.747(4) . ?
O1 C16 1.233(5) . ?
N1 C7 1.323(5) . ?
N1 C6 1.437(5) . ?
N1 H1A 0.8600 . ?
N2 C9 1.270(5) . ?
N2 C10 1.418(5) . ?
C1 C6 1.365(7) . ?
C1 C2 1.417(8) . ?
C1 H1B 0.9300 . ?
C2 C3 1.355(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.336(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.371(7) . ?
C5 H5A 0.9300 . ?
C7 C8 1.399(6) . ?
C8 C9 1.446(5) . ?
C8 C16 1.439(5) . ?
C10 C11 1.364(7) . ?
C10 C15 1.381(7) . ?
C11 C12 1.380(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.335(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(7) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.511(5) . ?
C17 C18 1.366(6) . ?
C17 C22 1.384(6) . ?
C18 C19 1.388(6) . ?
C19 C20 1.382(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.353(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.389(6) . ?
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 -2.6(2) . . . . ?
C6 C1 C2 C3 1.2(9) . . . . ?
C1 C2 C3 C4 0.7(10) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C3 C4 C5 C6 0.0(10) . . . . ?
C2 C1 C6 C5 -2.5(8) . . . . ?
C2 C1 C6 N1 179.5(5) . . . . ?
C4 C5 C6 C1 2.0(8) . . . . ?
C4 C5 C6 N1 180.0(5) . . . . ?
C7 N1 C6 C1 -101.0(6) . . . . ?
C7 N1 C6 C5 80.9(6) . . . . ?
C6 N1 C7 C8 -174.4(5) . . . . ?
C6 N1 C7 S2 7.0(6) . . . . ?
S1 S2 C7 N1 179.4(4) . . . . ?
S1 S2 C7 C8 0.8(4) . . . . ?
N1 C7 C8 C9 -176.3(5) . . . . ?
S2 C7 C8 C9 2.2(6) . . . . ?
N1 C7 C8 C16 3.8(7) . . . . ?
S2 C7 C8 C16 -177.7(3) . . . . ?
C10 N2 C9 C8 176.9(4) . . . . ?
C10 N2 C9 S1 -3.3(6) . . . . ?
C7 C8 C9 N2 175.2(5) . . . . ?
C16 C8 C9 N2 -4.8(8) . . . . ?
C7 C8 C9 S1 -4.5(5) . . . . ?
C16 C8 C9 S1 175.4(4) . . . . ?
S2 S1 C9 N2 -175.6(4) . . . . ?
S2 S1 C9 C8 4.2(3) . . . . ?
C9 N2 C10 C11 -72.5(6) . . . . ?
C9 N2 C10 C15 110.4(5) . . . . ?
C15 C10 C11 C12 -3.1(7) . . . . ?
N2 C10 C11 C12 179.8(4) . . . . ?
C10 C11 C12 C13 1.4(8) . . . . ?
C11 C12 C13 C14 1.2(9) . . . . ?
C12 C13 C14 C15 -2.1(10) . . . . ?
C11 C10 C15 C14 2.2(8) . . . . ?
N2 C10 C15 C14 179.3(5) . . . . ?
C13 C14 C15 C10 0.4(9) . . . . ?
C7 C8 C16 O1 -9.0(7) . . . . ?
C9 C8 C16 O1 171.1(5) . . . . ?
C7 C8 C16 C17 169.5(4) . . . . ?
C9 C8 C16 C17 -10.4(7) . . . . ?
O1 C16 C17 C18 103.4(5) . . . . ?
C8 C16 C17 C18 -75.2(6) . . . . ?
O1 C16 C17 C22 -70.3(6) . . . . ?
C8 C16 C17 C22 111.1(5) . . . . ?
C22 C17 C18 C19 1.1(7) . . . . ?
C16 C17 C18 C19 -172.5(4) . . . . ?
C22 C17 C18 Cl2 -178.9(3) . . . . ?
C16 C17 C18 Cl2 7.5(6) . . . . ?
C17 C18 C19 C20 -1.6(7) . . . . ?
Cl2 C18 C19 C20 178.4(4) . . . . ?
C18 C19 C20 C21 0.1(7) . . . . ?
C19 C20 C21 C22 1.8(8) . . . . ?
C19 C20 C21 Cl1 -176.9(4) . . . . ?
C18 C17 C22 C21 0.8(6) . . . . ?
C16 C17 C22 C21 174.7(4) . . . . ?
C20 C21 C22 C17 -2.3(7) . . . . ?
Cl1 C21 C22 C17 176.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173421
