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_4037002
_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 Br N2 O S'
_chemical_formula_sum            'C22 H17 Br N2 O S'
_chemical_formula_weight         437.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.208(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0643(10)
_cell_length_b                   19.913(4)
_cell_length_c                   13.651(2)
_cell_measurement_reflns_used    787
_cell_measurement_temperature    295.38(10)
_cell_measurement_theta_max      21.0940
_cell_measurement_theta_min      4.0860
_cell_volume                     1883.7(5)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.38(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  -51.00   63.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  -60.0000 95

  2 omega   -7.00   55.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -120.0000 52

  3 omega  -19.00    7.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -60.0000 22

  4 omega   -4.00   23.60   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   90.0000 23
;
_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      0.0760566000
_diffrn_orient_matrix_UB_12      -0.0206560000
_diffrn_orient_matrix_UB_13      -0.0096244000
_diffrn_orient_matrix_UB_21      -0.0417199000
_diffrn_orient_matrix_UB_22      -0.0280360000
_diffrn_orient_matrix_UB_23      0.0199333000
_diffrn_orient_matrix_UB_31      -0.0543416000
_diffrn_orient_matrix_UB_32      -0.0074595000
_diffrn_orient_matrix_UB_33      -0.0481266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.2656
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6997
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44738
_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    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.734
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.734
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0554P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                2129
_reflns_number_total             6997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01232_si_001.cif
_cod_data_source_block           xieting1204_twin1_hklf4
_cod_database_code               4037002
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5875(13) 0.4125(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'