#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:22:04 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240768.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_7240768
loop_
_publ_author_name
'Li, Xiao-Yun'
'Liu, Yan'
'Chen, Xiao-Lan'
'Lu, Xin-Yuan'
'Liang, Xing-Xing'
'Zhu, Shan-Shan'
'Wei, Chuan-Wan'
'Qu, Ling-Bo'
'Yu, Bing'
_publ_section_title
;
 6π-Electrocyclization in water: microwave-assisted synthesis of
 polyheterocyclic-fused quinoline-2-thiones
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              4445
_journal_page_last               4449
_journal_paper_doi               10.1039/C9GC04445K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 F3 N3 S, C2 H7 O S'
_chemical_formula_sum            'C17 H15 F3 N3 O S2'
_chemical_formula_weight         398.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc240yx1
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-21 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.410(3)
_cell_angle_beta                 103.927(3)
_cell_angle_gamma                93.498(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1450(6)
_cell_length_b                   10.3161(9)
_cell_length_c                   12.2769(11)
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.508
_cell_measurement_theta_min      2.371
_cell_volume                     855.32(13)
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4416
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         2.956
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0896P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2361
_reflns_number_total             3001
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc04445k2.cif
_cod_data_source_block           191108e
_cod_depositor_comments
;Adding full bibliography for 7240768.cif.

 Adding full bibliography for 7240768.cif.
;
_cod_database_code               7240768
_shelxl_version_number           2013-2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.865
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1a)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.14643(14) 0.09487(7) -0.10922(7) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.2213(3) 0.3293(2) -0.15639(17) 0.0356(5) Uani 1 1 d . . . . .
H1 H 0.2171 0.2825 -0.2234 0.043 Uiso 1 1 calc R . . . .
N2 N 0.1888(3) 0.31731(19) 0.13481(16) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.2625(4) 0.5499(2) -0.0348(2) 0.0298(6) Uani 1 1 d . . . . .
N3 N 0.2402(3) 0.54190(19) 0.16465(16) 0.0320(5) Uani 1 1 d . . . . .
F2 F 0.1226(3) 0.65502(17) 0.37690(15) 0.0647(6) Uani 1 1 d . . . . .
C2 C 0.2036(4) 0.3465(2) 0.0318(2) 0.0308(6) Uani 1 1 d . . . . .
C3 C 0.2354(4) 0.4841(2) 0.0537(2) 0.0298(6) Uani 1 1 d . . . . .
C4 C 0.2583(4) 0.4660(2) -0.1410(2) 0.0314(6) Uani 1 1 d . . . . .
C5 C 0.3256(4) 0.7406(3) -0.1109(2) 0.0419(7) Uani 1 1 d . . . . .
H5 H 0.3475 0.8324 -0.1020 0.050 Uiso 1 1 calc R . . . .
C6 C 0.1909(4) 0.2612(2) -0.0769(2) 0.0356(6) Uani 1 1 d . . . . .
C7 C 0.2137(4) 0.4401(2) 0.2122(2) 0.0303(6) Uani 1 1 d . . . . .
F3 F 0.4200(3) 0.62933(18) 0.43200(16) 0.0661(6) Uani 1 1 d . . . . .
F1 F 0.2174(4) 0.5548(2) 0.51213(15) 0.0821(7) Uani 1 1 d . . . . .
C8 C 0.2907(4) 0.5210(3) -0.2308(2) 0.0376(6) Uani 1 1 d . . . . .
H8 H 0.2894 0.4661 -0.3010 0.045 Uiso 1 1 calc R . . . .
C9 C 0.1604(4) 0.1986(2) 0.1667(2) 0.0388(6) Uani 1 1 d . . . . .
H9 H 0.1437 0.1183 0.1133 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2095(4) 0.4385(2) 0.3267(2) 0.0340(6) Uani 1 1 d . . . . .
C11 C 0.3244(4) 0.6556(3) -0.2149(2) 0.0413(7) Uani 1 1 d . . . . .
H11 H 0.3472 0.6918 -0.2747 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2943(4) 0.6874(2) -0.0223(2) 0.0360(6) Uani 1 1 d . . . . .
H12 H 0.2942 0.7435 0.0470 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1824(4) 0.3205(3) 0.3576(2) 0.0403(7) Uani 1 1 d . . . . .
H13 H 0.1806 0.3196 0.4330 0.048 Uiso 1 1 calc R . . . .
C14 C 0.1571(4) 0.2001(3) 0.2761(2) 0.0421(7) Uani 1 1 d . . . . .
H14 H 0.1377 0.1201 0.2980 0.051 Uiso 1 1 calc R . . . .
C15 C 0.2410(5) 0.5690(3) 0.4110(2) 0.0432(7) Uani 1 1 d . . . . .
S2 S 0.35515(12) 0.09473(7) -0.41493(6) 0.0466(3) Uani 1 1 d . . . . .
O1 O 0.2180(3) 0.1923(2) -0.38915(18) 0.0535(6) Uani 1 1 d . . . . .
H1A H 0.1107 0.1525 -0.3979 0.080 Uiso 1 1 calc GR . . . .
C16 C 0.5461(5) 0.1182(3) -0.2882(3) 0.0631(9) Uani 1 1 d . . . . .
H16A H 0.6059 0.2085 -0.2683 0.095 Uiso 1 1 calc GR . . . .
H16B H 0.6408 0.0588 -0.3010 0.095 Uiso 1 1 calc GR . . . .
H16C H 0.4951 0.0999 -0.2266 0.095 Uiso 1 1 calc GR . . . .
C17 C 0.2490(6) -0.0648(3) -0.4093(3) 0.0650(10) Uani 1 1 d . . . . .
H17A H 0.2129 -0.0585 -0.3382 0.098 Uiso 1 1 calc GR . . . .
H17B H 0.3414 -0.1281 -0.4142 0.098 Uiso 1 1 calc GR . . . .
H17C H 0.1358 -0.0934 -0.4725 0.098 Uiso 1 1 calc GR . . . .
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'
F F 0.0171 0.0103 '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'
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
C4 N1 H1 116.5 . . ?
C6 N1 H1 116.5 . . ?
C6 N1 C4 126.9(2) . . ?
C2 N2 C7 105.67(19) . . ?
C9 N2 C2 132.1(2) . . ?
C9 N2 C7 122.2(2) . . ?
C4 C1 C3 115.7(2) . . ?
C12 C1 C3 125.1(2) . . ?
C12 C1 C4 119.2(2) . . ?
C7 N3 C3 104.17(19) . . ?
N2 C2 C3 105.1(2) . . ?
N2 C2 C6 130.8(2) . . ?
C3 C2 C6 124.1(2) . . ?
N3 C3 C1 127.3(2) . . ?
N3 C3 C2 112.3(2) . . ?
C2 C3 C1 120.4(2) . . ?
N1 C4 C1 120.1(2) . . ?
N1 C4 C8 120.1(2) . . ?
C8 C4 C1 119.7(2) . . ?
C11 C5 H5 120.4 . . ?
C12 C5 H5 120.4 . . ?
C12 C5 C11 119.2(2) . . ?
N1 C6 S1 121.23(18) . . ?
N1 C6 C2 112.6(2) . . ?
C2 C6 S1 126.1(2) . . ?
N2 C7 C10 117.3(2) . . ?
N3 C7 N2 112.7(2) . . ?
N3 C7 C10 129.9(2) . . ?
C4 C8 H8 120.3 . . ?
C11 C8 C4 119.5(2) . . ?
C11 C8 H8 120.3 . . ?
N2 C9 H9 120.4 . . ?
C14 C9 N2 119.1(2) . . ?
C14 C9 H9 120.4 . . ?
C7 C10 C15 117.8(2) . . ?
C13 C10 C7 120.0(2) . . ?
C13 C10 C15 122.1(2) . . ?
C5 C11 H11 119.2 . . ?
C8 C11 C5 121.7(2) . . ?
C8 C11 H11 119.2 . . ?
C1 C12 H12 119.6 . . ?
C5 C12 C1 120.7(2) . . ?
C5 C12 H12 119.6 . . ?
C10 C13 H13 119.9 . . ?
C10 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 121.1(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
F2 C15 F3 106.1(2) . . ?
F2 C15 F1 106.5(3) . . ?
F2 C15 C10 113.6(2) . . ?
F3 C15 C10 112.2(2) . . ?
F1 C15 F3 106.0(2) . . ?
F1 C15 C10 111.9(2) . . ?
O1 S2 C16 106.14(15) . . ?
O1 S2 C17 107.00(16) . . ?
C16 S2 C17 97.49(16) . . ?
S2 O1 H1A 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S2 C17 H17A 109.5 . . ?
S2 C17 H17B 109.5 . . ?
S2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
S1 C6 1.676(3) . ?
N1 H1 0.8600 . ?
N1 C4 1.385(3) . ?
N1 C6 1.359(3) . ?
N2 C2 1.383(3) . ?
N2 C7 1.398(3) . ?
N2 C9 1.375(3) . ?
C1 C3 1.434(3) . ?
C1 C4 1.408(3) . ?
C1 C12 1.394(3) . ?
N3 C3 1.366(3) . ?
N3 C7 1.323(3) . ?
F2 C15 1.321(3) . ?
C2 C3 1.385(3) . ?
C2 C6 1.425(3) . ?
C4 C8 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C11 1.396(4) . ?
C5 C12 1.369(4) . ?
C7 C10 1.417(3) . ?
F3 C15 1.330(4) . ?
F1 C15 1.328(3) . ?
C8 H8 0.9300 . ?
C8 C11 1.362(4) . ?
C9 H9 0.9300 . ?
C9 C14 1.347(4) . ?
C10 C13 1.362(4) . ?
C10 C15 1.494(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.403(4) . ?
C14 H14 0.9300 . ?
S2 O1 1.489(2) . ?
S2 C16 1.769(3) . ?
S2 C17 1.791(3) . ?
O1 H1A 0.8200 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
