Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives.
Zhang, Xi; Wang, Tong-Lin; Huo, Cong-De; Wang, Xi-Cun; Quan, Zheng-Jun; Chemical communications (Cambridge, England) 54 (2018) 3114–3117; doi:10.1039/c8cc00062j

data_7121344
_publ_section_title
;
 Base-controlled chemoselectivity reaction of vinylanilines with
 isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline
 derivatives.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3114
_journal_page_last               3117
_journal_paper_doi               10.1039/c8cc00062j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41
_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
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1z6v56
_audit_creation_date             2018-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-02-13 deposited with the CCDC.
2018-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.699(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4749(19)
_cell_length_b                   10.8598(8)
_cell_length_c                   8.3747(5)
_cell_measurement_reflns_used    1896
_cell_measurement_temperature    120
_cell_measurement_theta_max      69.8650
_cell_measurement_theta_min      4.5880
_cell_volume                     1755.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_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    118.00 145.00   1.00    1.00    --  108.00  50.00  30.00   27
  2  \w    148.00 175.00   1.00    1.00    --  108.00  50.00  30.00   27
  3  \w    115.00 172.00   1.00    1.00    --  108.00 111.00   0.00   57
  4  \w    130.00 175.00   1.00    1.00    --  108.00 111.00 150.00   45
  5  \w    112.00 173.00   1.00    1.00    --  108.00  63.00 150.00   61
  6  \w     90.00 163.00   1.00    1.00    --  108.00  77.00 120.00   73
  7  \w     93.00 178.00   1.00    1.00    --  108.00  50.00  90.00   85
  8  \w     77.00 104.00   1.00    1.00    --  108.00-111.00-120.00   27
  9  \w     52.00  78.00   1.00    1.00    --   54.00 -38.00 -90.00   26
 10  \w     42.00 107.00   1.00    1.00    --  108.00-111.00   0.00   65
 11  \w     60.00 130.00   1.00    1.00    --  108.00 -50.00   0.00   70
 12  \w     28.00 117.00   1.00    1.00    --   54.00  38.00-150.00   89
 13  \w     39.00  68.00   1.00    1.00    --    0.00  38.00 -60.00   29
 14  \w      1.00  30.00   1.00    1.00    --    0.00  38.00 -60.00   29
 15  \w    -17.00  78.00   1.00    1.00    --   54.00 -38.00  30.00   95
 16  \w     23.00  86.00   1.00    1.00    --   54.00-125.00 -90.00   63
 17  \w    -72.00 -32.00   1.00    1.00    --    0.00 -38.00 150.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013136000
_diffrn_orient_matrix_UB_12      0.0234692000
_diffrn_orient_matrix_UB_13      0.1809682000
_diffrn_orient_matrix_UB_21      -0.0526976000
_diffrn_orient_matrix_UB_22      0.1047465000
_diffrn_orient_matrix_UB_23      -0.0412522000
_diffrn_orient_matrix_UB_31      -0.0598428000
_diffrn_orient_matrix_UB_32      -0.0929672000
_diffrn_orient_matrix_UB_33      -0.0007815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6373
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.699
_diffrn_reflns_theta_min         4.582
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0516P)^2^+0.5974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2600
_reflns_number_total             3251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00062j2.cif
_cod_data_source_block           xray_0211
_cod_depositor_comments          'Adding full bibliography for 7121344.cif.'
_cod_database_code               7121344
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.76
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C15(H15),
  C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2018-02-11
_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.611