A Palladium-Catalyzed Method for the Synthesis of 2-(α-Styryl)-2,3-dihydroquinazolin-4-ones and 3-(α-Styryl)-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide: Access to 2-(α-Styryl)quinazolin-4(3H)-ones and 3-(α-Styryl)-1,2,4-benzothiadiazine-1,1-dioxides.
Kundu, Priyanka; Mondal, Amrita; Chowdhury, Chinmay; The Journal of organic chemistry 81 (2016) 6596–6608; doi:10.1021/acs.joc.6b01242

data_4037006
_publ_section_title
;
 A Palladium-Catalyzed Method for the Synthesis of
 2-(\a-Styryl)-2,3-dihydroquinazolin-4-ones and
 3-(\a-Styryl)-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide: Access to
 2-(\a-Styryl)quinazolin-4(3H)-ones and
 3-(\a-Styryl)-1,2,4-benzothiadiazine-1,1-dioxides.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6596
_journal_page_last               6608
_journal_paper_doi               10.1021/acs.joc.6b01242
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H22 N2 O3 S'
_chemical_formula_sum            'C24 H22 N2 O3 S'
_chemical_formula_weight         418.49
_chemical_melting_point          465.6(5)
_chemical_name_systematic
3-methyl-2-(1-phenylvinyl)-1-tosyl-2,3-dihydroquinazolin-4(1H)-one
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                82.627(10)
_cell_angle_beta                 81.964(10)
_cell_angle_gamma                77.726(9)
_cell_formula_units_Z            2
_cell_length_a                   8.0522(11)
_cell_length_b                   11.3712(17)
_cell_length_c                   12.2775(19)
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.343
_cell_measurement_theta_min      1.842
_cell_volume                     1082.0(3)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19686
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.373
_diffrn_reflns_theta_min         1.842
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.800955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0786 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8010.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0760P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2570
_reflns_number_total             4854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            9aa.cif
_cod_data_source_block           cc_amr2_22_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '192-193 degree centigrade'
was changed to '465.6(5)' -- it was converted from degrees Celsius(C)
to Kelvins(K), the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037006
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H00F), C5(H00H), C6(H00N), C7(H00D), C12(H00P), C13(H00T), C14(H00S),
 C15(H00Q), C16(H00L), C18(H00I), C19(H00M), C21(H00K), C22(H00E)
2.c Idealised Me refined as rotating group:
 C23(H00O,H00R,H00U), C24(H00C,H00G,H00J)
;
_shelx_res_checksum              50102
_shelx_hkl_checksum              18259
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'