Selenium-Catalyzed Oxidative C-H Amination of ( E)-3-(Arylamino)-2-styrylquinazolin-4(3 H)-ones: A Metal-Free Synthesis of 1,2-Diarylpyrazolo[5,1- b]quinazolin-9(1 H)-ones.
Zhang, Yetong; Shao, Yinlin; Gong, Julin; Zhu, Jianghe; Cheng, Tianxing; Chen, Jiuxi; The Journal of organic chemistry 84 (2019) 2798–2807; doi:10.1021/acs.joc.8b03179

data_4033733
_publ_section_title
;
 Selenium-Catalyzed Oxidative C-H Amination of (
 E)-3-(Arylamino)-2-styrylquinazolin-4(3 H)-ones: A Metal-Free Synthesis
 of 1,2-Diarylpyrazolo[5,1- b]quinazolin-9(1 H)-ones.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2798
_journal_page_last               2807
_journal_paper_doi               10.1021/acs.joc.8b03179
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'I, C23 H18 N3 O'
_chemical_formula_sum            'C23 H18 I N3 O'
_chemical_formula_weight         479.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.229(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.990(2)
_cell_length_b                   7.8789(10)
_cell_length_c                   31.404(5)
_cell_measurement_reflns_used    6516
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      25.073
_cell_measurement_theta_min      2.490
_cell_volume                     4056.2(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.58
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            23714
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.495
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.597
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1370 before and 0.0805 after correction. The Ratio of minimum to maximum transmission is 0.7515. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.318
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.00089(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4611
_refine_ls_number_restraints     294
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+13.7141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             4611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03179_si_002.cif
_cod_data_source_block           d8v17136
_cod_original_cell_volume        4056.1(10)
_cod_database_code               4033733
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C12 = C17-C16 = C16-C15 = C15-C14 = C14-C13 = C13-C12
 1.39 with sigma of 0.02
 C17'-C12 = C17'-C16' = C16'-C15 = C15-C14' = C14'-C13' = C13'-C12
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C19' \\sim C20'
\\sim C21' \\sim C22' \\sim C23': within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C12 \\sim C15 \\sim C13 \\sim C14 \\sim C16 \\sim C17 \\sim C13' \\sim C14'
\\sim C16' \\sim C17': within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Fixed Sof: H15A(0.5) H15(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C19(0.5) H19(0.5) C20(0.5) H20(0.5) C21(0.5)
 H21(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5) C13'(0.5) H13'(0.5) C14'(0.5)
 H14'(0.5) C16'(0.5) H16'(0.5) C17'(0.5) H17'(0.5) C19'(0.5) H19'(0.5)
 C20'(0.5) H20'(0.5) C21'(0.5) H21'(0.5) C22'(0.5) H22'(0.5) C23'(0.5) H23'(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15A), C15(H15), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C13'(H13'), C14'(H14'), C16'(H16'), C17'(H17'), C19'(H19'), C20'(H20'),
 C21'(H21'), C22'(H22'), C23'(H23')
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              51097
_shelx_hkl_checksum              16305
_olex2_submission_special_instructions 'No special instructions were received'