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_4027063
_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 Cl N4, C H4 O'
_chemical_formula_sum            'C12 H16 Cl N4 O'
_chemical_formula_weight         267.74
_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                 110.580(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4119(4)
_cell_length_b                   12.2748(4)
_cell_length_c                   10.7295(4)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2092
_cell_measurement_theta_min      3.3127
_cell_volume                     1283.76(9)
_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
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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      293.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
1 omega  -65.00  -39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
-      -16.8924  179.0000 -180.0000 26

2 omega  -48.00   10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
-       20.0174  -62.0000   54.0000 58

3 omega   -5.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
-       20.0174   38.0000 -180.0000 91

4 omega   34.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
-       20.0174  179.0000  -30.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0373197
_diffrn_orient_matrix_UB_12      -0.0231304
_diffrn_orient_matrix_UB_13      -0.0629128
_diffrn_orient_matrix_UB_21      0.0559539
_diffrn_orient_matrix_UB_22      -0.0350925
_diffrn_orient_matrix_UB_23      0.0058931
_diffrn_orient_matrix_UB_31      -0.0277559
_diffrn_orient_matrix_UB_32      -0.0396919
_diffrn_orient_matrix_UB_33      0.03146
_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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5362
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.98863
_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    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0419P)^2^+0.3114P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                1922
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2023697_si_001.cif
_cod_data_source_block           110326_S1_YP
_cod_original_cell_volume        1283.76(8)
_cod_database_code               4027063