6π-Electrocyclization in water: microwave-assisted synthesis of polyheterocyclic-fused quinoline-2-thiones
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; Green Chemistry 22 (2020) 4445–4449; doi:10.1039/C9GC04445K

data_7240768
_publ_section_title
;
 6\p-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/[\s^2^(Fo^2^)+(0.0896P)^2^]
 where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              10672
_olex2_submission_special_instructions 'No special instructions were received'