Facile “on water” domino reactions for the expedient synthesis of 2H-thiopyrano[2,3-b]quinolines
Vivek Kumar, Sundaravel; Muthusubramanian, Shanmugam; Subbu, Perumal; RSC Adv.  (2015) –; doi:10.1039/C5RA04795A

data_7219976
_publ_section_title
;
 Facile &#x201C;on water&#x201D; domino reactions for the expedient
 synthesis of 2H-thiopyrano[2,3-b]quinolines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA04795A
_journal_year                    2015
_chemical_formula_moiety         'C18 H11 Br N2 O2 S'
_chemical_formula_sum            'C18 H11 Br N2 O2 S'
_chemical_formula_weight         399.26
_chemical_melting_point          471.15
_chemical_name_common
;
2-(4-bromophenyl)-3-nitro-2H-thiopyrano[2,3-b]quinoline
;
_chemical_name_systematic
;
2-(4-bromophenyl)-3-nitro-2H-thiopyrano[2,3-b]quinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-03-13 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.7056(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.57240(10)
_cell_length_b                   12.7939(3)
_cell_length_c                   19.4514(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1620.83(6)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD Area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13135
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.646
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       Block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.8627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2343
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra04795a2.cif
_cod_data_source_block           TQ4
_cod_database_code               7219976
_shelx_estimated_absorpt_t_min   0.501
_shelx_estimated_absorpt_t_max   0.739
_shelxl_version_number           2013-4
_shelx_res_checksum              53557
_shelx_hkl_checksum              98467