Synthesis of 2,4-Diaminoquinazolines and Tricyclic Quinazolines by Cascade Reductive Cyclization of Methyl N-Cyano-2-nitrobenzimidates
Ping Yin; Nan Liu; Yu-Xing Deng; Yue Chen; Yong Deng; Ling He; Journal of Organic Chemistry 77 (2012) 2649–2658; doi:10.1021/jo2023697

data_4027064
_publ_section_title
;
 Synthesis of 2,4-Diaminoquinazolines and Tricyclic Quinazolines by
 Cascade Reductive Cyclization of Methyl N-Cyano-2-nitrobenzimidates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2649
_journal_page_last               2658
_journal_paper_doi               10.1021/jo2023697
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C11 H11 N3 O'
_chemical_formula_sum            'C11 H11 N3 O'
_chemical_formula_weight         201.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.634(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.80481(14)
_cell_length_b                   14.0954(4)
_cell_length_c                   11.0624(3)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    150.1
_cell_measurement_theta_max      28.9838
_cell_measurement_theta_min      2.8844
_cell_volume                     903.32(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      150.1
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega  -87.00   12.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
-      -16.8924  -77.0000 -180.0000 132

2 omega  -84.00  -51.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
-      -16.8924  162.0000   19.0000 44

3 omega  -49.00   31.25   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
-       19.8611    0.0000 -180.0000 107
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0196458
_diffrn_orient_matrix_UB_12      -0.0495435
_diffrn_orient_matrix_UB_13      -0.0051027
_diffrn_orient_matrix_UB_21      -0.0228979
_diffrn_orient_matrix_UB_22      0.0050327
_diffrn_orient_matrix_UB_23      -0.0634362
_diffrn_orient_matrix_UB_31      0.1186377
_diffrn_orient_matrix_UB_32      -0.0072483
_diffrn_orient_matrix_UB_33      -0.0088809
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3684
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0504P)^2^+0.8528P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1497
_reflns_number_total             1836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023697_si_002.cif
_cod_data_source_block           110315_S1_YP
_cod_database_code               4027064