Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines.
Bandyopadhyay, Debashruti; Thirupathi, Annaram; Radhakrishnan, Divya; Panigrahi, Adyasha; Peruncheralathan, S.; Organic & biomolecular chemistry 19 (2021) 8544–8553; doi:10.1039/d1ob01151k

data_7158297
_publ_section_title
;
 Triflic acid-mediated N-heteroannulation of
 \b-anilino-\b-(methylthio)acrylonitriles: a facile synthesis of
 4-amino-2-(methylthio)quinolines.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8544
_journal_page_last               8553
_journal_paper_doi               10.1039/d1ob01151k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H18 N2 O2 S'
_chemical_formula_sum            'C15 H18 N2 O2 S'
_chemical_formula_weight         290.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2021-06-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000(9)
_cell_angle_beta                 93.9407(9)
_cell_angle_gamma                90.0000(10)
_cell_formula_units_Z            4
_cell_length_a                   9.31410(10)
_cell_length_b                   7.60332(10)
_cell_length_c                   20.7811(2)
_cell_measurement_reflns_used    8739
_cell_measurement_temperature    297.4(3)
_cell_measurement_theta_max      74.8940
_cell_measurement_theta_min      4.7700
_cell_volume                     1468.20(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.4(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -105.00 -35.00   0.50    0.83    --  -38.50 -36.00-168.00  140
  2  \w    -42.00  28.00   0.50    0.83    --  -38.50  36.00 -12.00  140
  3  \w     46.00 116.00   0.50    0.83    --   49.56  36.00 -12.00  140
  4  \w    -17.00  53.00   0.50    0.83    --   49.56 -36.00-168.00  140
  5  \w     36.00 106.00   0.50    3.29    --  102.63 -36.00-168.00  140
  6  \w    100.00 169.00   0.50    3.29    --  102.63  36.00 -12.00  138
  7  \w    -86.00  -6.00   0.50    0.83    --  -38.50 125.00  60.00  160
  8  \w     46.00 116.00   0.50    0.83    --   49.56  38.00 150.00  140
  9  \w    103.00 167.00   0.50    3.29    --  102.63  77.00 -90.00  128
 10  \w     97.00 168.00   0.50    3.29    --  102.63 125.00-120.00  142
 11  \w    103.00 167.00   0.50    3.29    --  102.63  77.00 120.00  128
 12  \w     98.00 167.00   0.50    3.29    --  102.63  45.00  60.00  138
 13  \w     34.00 107.00   0.50    3.29    --  102.63 -94.00  30.00  146
 14  \w     34.00 107.00   0.50    3.29    --  102.63 -94.00 150.00  146
 15  \w     38.00 107.00   0.50    3.29    --  102.63 -45.00 -90.00  138
 16  \w     98.00 167.00   0.50    3.29    --  102.63  45.00 150.00  138
 17  \w     98.00 167.00   0.50    3.29    --  102.63  45.00-150.00  138
 18  \w     43.00  70.00   0.50    3.29    --  102.63 -94.00   0.00   54
 19  \w     64.00 105.00   0.50    3.29    --  102.63 -45.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1630217000
_diffrn_orient_matrix_UB_12      0.0358459000
_diffrn_orient_matrix_UB_13      0.0018058000
_diffrn_orient_matrix_UB_21      -0.0228741000
_diffrn_orient_matrix_UB_22      0.1781107000
_diffrn_orient_matrix_UB_23      0.0331185000
_diffrn_orient_matrix_UB_31      0.0196981000
_diffrn_orient_matrix_UB_32      -0.0896956000
_diffrn_orient_matrix_UB_33      0.0664954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11800
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.421
_diffrn_reflns_theta_min         4.265
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.4866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2769
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01151k2.cif
_cod_data_source_block           peru-db-978
_cod_depositor_comments          'Adding full bibliography for 7158297.cif.'
_cod_database_code               7158297
_chemical_oxdiff_formula         'C60 H72 N8 O8 S4 '
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.587
_diffrn_oxdiff_digest_frames
;
01d1cbffb85421faf64b7e7f0ab1b8c28900038a7b5
;
_diffrn_oxdiff_digest_hkl
;
0153dc9a41d032b6b662c2e5fe68df313125c4
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9)
2.c X=CH2 refined with riding coordinates:
 N18(H18A,H18B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C12(H12A,H12B,H12C), C16(H16A,H16B,
 H16C)
;
_shelx_res_checksum              26145
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.676