Catalyst-Free Chemoselective Synthesis of 3,4-Dihydroquinazoline-2-thiones and 2-Imino[1,3]benzothiazines.
Xie, Ting; Xiao, Yu; Zhao, Shuai; Hu, Xiu-Qin; Xu, Peng-Fei; The Journal of organic chemistry 81 (2016) 10499–10505; doi:10.1021/acs.joc.6b01232

data_4037001
_publ_section_title
;
 Catalyst-Free Chemoselective Synthesis of
 3,4-Dihydroquinazoline-2-thiones and 2-Imino[1,3]benzothiazines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10499
_journal_page_last               10505
_journal_paper_doi               10.1021/acs.joc.6b01232
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H17 Cl N2 O S, C2 H6 O S'
_chemical_formula_sum            'C26 H23 Cl2 N0.5 O2 S'
_chemical_formula_weight         477.41
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                95.186(15)
_cell_angle_beta                 94.476(12)
_cell_angle_gamma                102.710(14)
_cell_formula_units_Z            2
_cell_length_a                   9.5835(13)
_cell_length_b                   10.586(2)
_cell_length_c                   11.7122(18)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    293.42(10)
_cell_measurement_theta_max      26.5850
_cell_measurement_theta_min      3.9420
_cell_volume                     1148.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -39.00   -9.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479   57.0000  150.0000 15

  2 omega   -5.00   25.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   30.0000 15

  3 omega  -10.00   46.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -120.0000 28

  4 omega  -17.00   57.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -90.0000 37

  5 omega   -6.00   24.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 15

  6 omega  -46.00   38.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  150.0000 42

  7 omega  -48.00   38.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   30.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0411303000
_diffrn_orient_matrix_UB_12      -0.0383475000
_diffrn_orient_matrix_UB_13      -0.0491204000
_diffrn_orient_matrix_UB_21      0.0184214000
_diffrn_orient_matrix_UB_22      -0.0564627000
_diffrn_orient_matrix_UB_23      0.0191349000
_diffrn_orient_matrix_UB_31      -0.0615189000
_diffrn_orient_matrix_UB_32      -0.0108628000
_diffrn_orient_matrix_UB_33      0.0309327000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             497
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.1631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                2847
_reflns_number_total             4525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01232_si_002.cif
_cod_data_source_block           zhaoshuai0412
_cod_original_cell_volume        1148.4(3)
_cod_original_formula_sum        'C26 H23 Cl2 N0.50 O2 S'
_cod_database_code               4037001
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), N12(H12), C15(H15), C16(H16),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_olex2_date_sample_data_collection 2015-04-15
_olex2_submission_special_instructions 'No special instructions were received'