#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:19:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180332 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/01/7200177.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_7200177
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            'C23 H17 Br N2 O S2'
_chemical_formula_weight         481.42
_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                108.64(3)
_cell_angle_beta                 96.27(3)
_cell_angle_gamma                96.96(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3729(13)
_cell_length_b                   12.941(3)
_cell_length_c                   13.413(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      1.62
_cell_volume                     1027.5(5)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4243
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.172
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0945
_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)+(0.1908P)²+1.1920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2769
_refine_ls_wR_factor_ref         0.3118
_reflns_number_gt                2220
_reflns_number_total             3546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808949c.txt
_cod_data_source_block           1i
_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_cell_volume        1027.5(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200177
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
Br1 Br 0.6087(2) -0.02178(13) 0.85777(11) 0.1280(7) Uani 1 1 d . A .
S1 S 0.2979(4) 0.39701(14) 0.89615(15) 0.0663(6) Uani 1 1 d . . .
S2 S 0.1294(4) 0.38710(14) 1.01682(15) 0.0618(6) Uani 1 1 d . . .
O1 O 0.1259(12) 0.0158(4) 0.9221(5) 0.093(2) Uani 1 1 d . . .
N1 N 0.0176(10) 0.2000(5) 1.0485(5) 0.0581(15) Uani 1 1 d . . .
H1A H 0.0167 0.1306 1.0363 0.070 Uiso 1 1 calc R . .
N2 N 0.3979(12) 0.2161(5) 0.7594(6) 0.078(2) Uani 1 1 d . . .
C1 C 0.0010(14) 0.2651(6) 1.2362(7) 0.067(2) Uani 1 1 d . . .
H1B H 0.1227 0.2350 1.2482 0.080 Uiso 1 1 calc R . .
C2 C -0.1015(18) 0.3196(7) 1.3213(7) 0.080(3) Uani 1 1 d . . .
H2B H -0.0485 0.3239 1.3902 0.096 Uiso 1 1 calc R . .
C3 C -0.2705(17) 0.3643(7) 1.3050(7) 0.078(2) Uani 1 1 d . . .
H3A H -0.3359 0.3998 1.3622 0.094 Uiso 1 1 calc R . .
C4 C -0.3516(15) 0.3589(8) 1.2035(9) 0.084(3) Uani 1 1 d . . .
H4A H -0.4692 0.3924 1.1927 0.100 Uiso 1 1 calc R . .
C5 C -0.2596(12) 0.3047(7) 1.1191(6) 0.0606(18) Uani 1 1 d . . .
H5A H -0.3165 0.2996 1.0505 0.073 Uiso 1 1 calc R . .
C6 C -0.0839(11) 0.2578(5) 1.1352(5) 0.0491(16) Uani 1 1 d . . .
C7 C 0.1128(11) 0.2451(5) 0.9856(5) 0.0500(16) Uani 1 1 d . . .
C8 C 0.1960(12) 0.1850(5) 0.8936(6) 0.0531(17) Uani 1 1 d . . .
C9 C 0.3025(11) 0.2523(5) 0.8389(6) 0.0508(16) Uani 1 1 d . . .
C10 C 0.4903(13) 0.2898(5) 0.7111(6) 0.060(2) Uani 1 1 d . . .
C11 C 0.7076(16) 0.3370(7) 0.7453(7) 0.073(2) Uani 1 1 d . . .
H11A H 0.7875 0.3229 0.8003 0.088 Uiso 1 1 calc R . .
C12 C 0.8017(14) 0.4067(7) 0.6937(7) 0.074(2) Uani 1 1 d . . .
H12A H 0.9440 0.4406 0.7162 0.089 Uiso 1 1 calc R . .
C13 C 0.6859(16) 0.4238(6) 0.6125(6) 0.068(2) Uani 1 1 d . . .
H13A H 0.7494 0.4682 0.5778 0.082 Uiso 1 1 calc R . .
C14 C 0.4799(18) 0.3776(7) 0.5809(8) 0.080(3) Uani 1 1 d . . .
H14A H 0.4032 0.3912 0.5246 0.095 Uiso 1 1 calc R . .
C15 C 0.3770(15) 0.3107(7) 0.6285(8) 0.075(2) Uani 1 1 d . . .
H15A H 0.2331 0.2801 0.6052 0.091 Uiso 1 1 calc R . .
C16 C 0.1850(13) 0.0678(6) 0.8646(7) 0.065(2) Uani 1 1 d . . .
C17 C 0.2270(15) 0.0029(6) 0.7542(8) 0.076(3) Uani 1 1 d . A .
C18 C 0.046(2) -0.0153(7) 0.6579(9) 0.118(3) Uani 1 1 d D . .
C19 C 0.103(3) -0.0824(9) 0.5650(9) 0.118(3) Uani 1 1 d . A .
H19A H 0.0040 -0.0988 0.5034 0.142 Uiso 1 1 calc R . .
C20 C 0.284(3) -0.1272(9) 0.5528(11) 0.127(5) Uani 1 1 d . . .
H20A H 0.3028 -0.1711 0.4855 0.153 Uiso 1 1 calc R A .
C21 C 0.442(2) -0.1081(8) 0.6400(10) 0.105(4) Uani 1 1 d . A .
H21A H 0.5693 -0.1361 0.6308 0.126 Uiso 1 1 calc R . .
C22 C 0.4073(16) -0.0455(7) 0.7424(8) 0.083(3) Uani 1 1 d . . .
C23A C -0.0707(17) 0.0741(9) 0.6837(9) 0.050(3) Uiso 0.80 1 d PD A 1
H23A H -0.1826 0.0634 0.6255 0.076 Uiso 0.80 1 calc PR A 1
H23B H 0.0241 0.1421 0.6964 0.076 Uiso 0.80 1 calc PR A 1
H23C H -0.1322 0.0773 0.7466 0.076 Uiso 0.80 1 calc PR A 1
C23B C -0.119(5) 0.045(3) 0.672(3) 0.043(11) Uiso 0.20 1 d PD A 2
H23D H -0.2162 0.0228 0.6058 0.065 Uiso 0.20 1 calc PR A 2
H23E H -0.0621 0.1220 0.6926 0.065 Uiso 0.20 1 calc PR A 2
H23F H -0.1932 0.0311 0.7258 0.065 Uiso 0.20 1 calc PR A 2
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'
Br Br -0.2901 2.4595 '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 96.8(2) . . ?
C7 S2 S1 95.3(2) . . ?
C7 N1 C6 125.3(5) . . ?
C7 N1 H1A 117.4 . . ?
C6 N1 H1A 117.4 . . ?
C9 N2 C10 120.0(6) . . ?
C6 C1 C2 118.1(8) . . ?
C6 C1 H1B 120.9 . . ?
C2 C1 H1B 120.9 . . ?
C3 C2 C1 121.1(8) . . ?
C3 C2 H2B 119.4 . . ?
C1 C2 H2B 119.4 . . ?
C2 C3 C4 120.4(8) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.0(8) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.1(8) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.3(7) . . ?
C5 C6 N1 121.7(6) . . ?
C1 C6 N1 118.0(7) . . ?
N1 C7 C8 124.7(6) . . ?
N1 C7 S2 116.8(5) . . ?
C8 C7 S2 118.4(5) . . ?
C7 C8 C16 120.4(6) . . ?
C7 C8 C9 115.3(6) . . ?
C16 C8 C9 124.2(6) . . ?
N2 C9 C8 125.4(6) . . ?
N2 C9 S1 120.6(5) . . ?
C8 C9 S1 114.0(5) . . ?
C15 C10 C11 119.6(7) . . ?
C15 C10 N2 121.8(8) . . ?
C11 C10 N2 118.5(8) . . ?
C10 C11 C12 118.3(8) . . ?
C10 C11 H11A 120.8 . . ?
C12 C11 H11A 120.8 . . ?
C13 C12 C11 120.1(8) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.5(7) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 122.5(9) . . ?
C13 C14 H14A 118.7 . . ?
C15 C14 H14A 118.7 . . ?
C10 C15 C14 118.9(9) . . ?
C10 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
O1 C16 C8 122.6(7) . . ?
O1 C16 C17 118.3(6) . . ?
C8 C16 C17 118.9(6) . . ?
C22 C17 C16 120.4(9) . . ?
C22 C17 C18 122.4(8) . . ?
C16 C17 C18 117.0(7) . . ?
C23B C18 C19 130(2) . . ?
C23B C18 C23A 17.7(18) . . ?
C19 C18 C23A 134.9(11) . . ?
C23B C18 C17 120.0(19) . . ?
C19 C18 C17 109.5(11) . . ?
C23A C18 C17 108.8(8) . . ?
C20 C19 C18 128.0(13) . . ?
C20 C19 H19A 116.0 . . ?
C18 C19 H19A 116.0 . . ?
C19 C20 C21 120.8(11) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C20 C21 C22 119.0(12) . . ?
C20 C21 H21A 120.5 . . ?
C22 C21 H21A 120.5 . . ?
C17 C22 C21 120.1(11) . . ?
C17 C22 Br1 119.9(7) . . ?
C21 C22 Br1 119.9(9) . . ?
C18 C23A H23A 109.5 . . ?
C18 C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C18 C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C18 C23B H23D 109.5 . . ?
C18 C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C18 C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
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
Br1 C22 1.817(11) . ?
S1 C9 1.788(6) . ?
S1 S2 2.066(3) . ?
S2 C7 1.736(6) . ?
O1 C16 1.234(9) . ?
N1 C7 1.327(9) . ?
N1 C6 1.433(9) . ?
N1 H1A 0.8600 . ?
N2 C9 1.271(10) . ?
N2 C10 1.421(9) . ?
C1 C6 1.373(10) . ?
C1 C2 1.409(13) . ?
C1 H1B 0.9300 . ?
C2 C3 1.312(13) . ?
C2 H2B 0.9300 . ?
C3 C4 1.379(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.362(12) . ?
C4 H4A 0.9300 . ?
C5 C6 1.365(10) . ?
C5 H5A 0.9300 . ?
C7 C8 1.428(9) . ?
C8 C16 1.431(9) . ?
C8 C9 1.461(9) . ?
C10 C15 1.373(12) . ?
C10 C11 1.407(12) . ?
C11 C12 1.418(11) . ?
C11 H11A 0.9300 . ?
C12 C13 1.341(12) . ?
C12 H12A 0.9300 . ?
C13 C14 1.336(13) . ?
C13 H13A 0.9300 . ?
C14 C15 1.377(12) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.521(11) . ?
C17 C22 1.374(13) . ?
C17 C18 1.572(15) . ?
C18 C23B 1.373(10) . ?
C18 C19 1.386(16) . ?
C18 C23A 1.421(9) . ?
C19 C20 1.36(2) . ?
C19 H19A 0.9300 . ?
C20 C21 1.394(19) . ?
C20 H20A 0.9300 . ?
C21 C22 1.411(13) . ?
C21 H21A 0.9300 . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
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 2.1(4) . . . . ?
C6 C1 C2 C3 -1.5(13) . . . . ?
C1 C2 C3 C4 -0.1(14) . . . . ?
C2 C3 C4 C5 1.6(15) . . . . ?
C3 C4 C5 C6 -1.5(13) . . . . ?
C4 C5 C6 C1 -0.1(12) . . . . ?
C4 C5 C6 N1 -180.0(7) . . . . ?
C2 C1 C6 C5 1.6(11) . . . . ?
C2 C1 C6 N1 -178.5(7) . . . . ?
C7 N1 C6 C5 63.8(10) . . . . ?
C7 N1 C6 C1 -116.1(8) . . . . ?
C6 N1 C7 C8 -173.9(7) . . . . ?
C6 N1 C7 S2 4.3(10) . . . . ?
S1 S2 C7 N1 177.8(6) . . . . ?
S1 S2 C7 C8 -3.9(6) . . . . ?
N1 C7 C8 C16 -1.5(12) . . . . ?
S2 C7 C8 C16 -179.7(6) . . . . ?
N1 C7 C8 C9 -177.5(7) . . . . ?
S2 C7 C8 C9 4.3(10) . . . . ?
C10 N2 C9 C8 178.2(7) . . . . ?
C10 N2 C9 S1 -4.0(12) . . . . ?
C7 C8 C9 N2 175.8(8) . . . . ?
C16 C8 C9 N2 0.0(14) . . . . ?
C7 C8 C9 S1 -2.2(9) . . . . ?
C16 C8 C9 S1 -177.9(7) . . . . ?
S2 S1 C9 N2 -178.4(7) . . . . ?
S2 S1 C9 C8 -0.4(6) . . . . ?
C9 N2 C10 C15 -90.4(11) . . . . ?
C9 N2 C10 C11 93.4(10) . . . . ?
C15 C10 C11 C12 1.0(12) . . . . ?
N2 C10 C11 C12 177.3(7) . . . . ?
C10 C11 C12 C13 -1.8(13) . . . . ?
C11 C12 C13 C14 1.5(13) . . . . ?
C12 C13 C14 C15 -0.3(14) . . . . ?
C11 C10 C15 C14 0.1(12) . . . . ?
N2 C10 C15 C14 -176.0(8) . . . . ?
C13 C14 C15 C10 -0.5(13) . . . . ?
C7 C8 C16 O1 -7.8(13) . . . . ?
C9 C8 C16 O1 167.7(8) . . . . ?
C7 C8 C16 C17 166.1(8) . . . . ?
C9 C8 C16 C17 -18.3(12) . . . . ?
O1 C16 C17 C22 -74.0(11) . . . . ?
C8 C16 C17 C22 111.7(9) . . . . ?
O1 C16 C17 C18 100.1(9) . . . . ?
C8 C16 C17 C18 -74.2(9) . . . . ?
C22 C17 C18 C23B -173(2) . . . . ?
C16 C17 C18 C23B 13(2) . . . . ?
C22 C17 C18 C19 -1.6(12) . . . . ?
C16 C17 C18 C19 -175.6(7) . . . . ?
C22 C17 C18 C23A -157.4(9) . . . . ?
C16 C17 C18 C23A 28.6(11) . . . . ?
C23B C18 C19 C20 169(3) . . . . ?
C23A C18 C19 C20 146.1(16) . . . . ?
C17 C18 C19 C20 -0.7(15) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C19 C20 C21 C22 3.0(18) . . . . ?
C16 C17 C22 C21 178.3(8) . . . . ?
C18 C17 C22 C21 4.6(12) . . . . ?
C16 C17 C22 Br1 -5.6(10) . . . . ?
C18 C17 C22 Br1 -179.3(6) . . . . ?
C20 C21 C22 C17 -5.2(15) . . . . ?
C20 C21 C22 Br1 178.7(8) . . . . ?
