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#$Date: 2016-03-21 03:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178449 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027064.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027064
loop_
_publ_author_name
'Ping Yin'
'Nan Liu'
'Yu-Xing Deng'
'Yue Chen'
'Yong Deng'
'Ling He'
_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
;
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
;
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       'ω 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/[σ²(Fo²)+(0.0504P)²+0.8528P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2148(3) 0.59663(12) 0.80470(13) 0.0378(4) Uani 1 1 d . . .
N1 N 0.2436(3) 0.57378(12) 0.54103(14) 0.0224(4) Uani 1 1 d . A .
N2 N 0.1032(3) 0.52935(12) 0.73068(14) 0.0249(4) Uani 1 1 d . A .
N3 N 0.4202(3) 0.45441(12) 0.65162(15) 0.0258(4) Uani 1 1 d . A .
H3 H 0.516(4) 0.4483(17) 0.593(2) 0.032(6) Uiso 1 1 d . . .
C1 C 0.0682(3) 0.63955(14) 0.52862(17) 0.0211(4) Uani 1 1 d . . .
C2 C 0.0573(3) 0.70185(15) 0.42889(18) 0.0253(4) Uani 1 1 d . . .
H2 H 0.183(4) 0.7000(16) 0.375(2) 0.027(6) Uiso 1 1 d . . .
C3 C -0.1206(4) 0.76587(15) 0.41143(19) 0.0269(5) Uani 1 1 d . . .
H3A H -0.115(4) 0.8081(18) 0.344(2) 0.039(7) Uiso 1 1 d . . .
C4 C -0.2978(4) 0.77013(15) 0.49181(19) 0.0272(5) Uani 1 1 d . . .
H4 H -0.427(4) 0.8131(17) 0.476(2) 0.033(6) Uiso 1 1 d . . .
C5 C -0.2863(3) 0.71251(14) 0.59191(19) 0.0254(5) Uani 1 1 d . . .
H5 H -0.401(4) 0.7145(16) 0.649(2) 0.028(6) Uiso 1 1 d . . .
C6 C -0.1029(3) 0.64841(14) 0.61246(17) 0.0218(4) Uani 1 1 d . . .
C7 C -0.0839(3) 0.59159(14) 0.72229(17) 0.0250(4) Uani 1 1 d . . .
C8 C 0.1366(4) 0.47134(19) 0.8409(2) 0.0401(5) Uani 1 1 d . . .
H8BD H 0.2189 0.5106 0.9041 0.048 Uiso 0.359(4) 1 calc PR A 2
H8BC H -0.0177 0.4569 0.8696 0.048 Uiso 0.359(4) 1 calc PR A 2
H8AB H 0.0791 0.5069 0.9101 0.048 Uiso 0.641(4) 1 calc PR A 1
H8AA H 0.0441 0.4126 0.8305 0.048 Uiso 0.641(4) 1 calc PR A 1
C9A C 0.3740(7) 0.4466(3) 0.8682(3) 0.0401(5) Uani 0.641(4) 1 d P A 1
H9AA H 0.3859 0.4035 0.9390 0.048 Uiso 0.641(4) 1 calc PR A 1
H9AB H 0.4638 0.5046 0.8894 0.048 Uiso 0.641(4) 1 calc PR A 1
C9B C 0.2552(12) 0.3867(5) 0.8331(6) 0.0401(5) Uani 0.359(4) 1 d P A 2
H9BA H 0.1521 0.3386 0.7932 0.048 Uiso 0.359(4) 1 calc PR A 2
H9BB H 0.3011 0.3638 0.9157 0.048 Uiso 0.359(4) 1 calc PR A 2
C10 C 0.4753(4) 0.39791(16) 0.75998(19) 0.0311(5) Uani 1 1 d . . .
H10D H 0.5991 0.4294 0.8110 0.037 Uiso 0.359(4) 1 calc PR A 2
H10C H 0.5316 0.3346 0.7367 0.037 Uiso 0.359(4) 1 calc PR A 2
H10B H 0.6448 0.3920 0.7742 0.037 Uiso 0.641(4) 1 calc PR A 1
H10A H 0.4095 0.3334 0.7493 0.037 Uiso 0.641(4) 1 calc PR A 1
C11 C 0.2549(3) 0.52044(13) 0.63888(16) 0.0206(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C7 N2 120.27(19)
O1 C7 C6 124.88(19)
N1 C1 C2 119.60(17)
N1 C1 C6 122.84(17)
N1 C11 N2 123.24(17)
N1 C11 N3 118.81(17)
N2 C7 C6 114.83(16)
N3 C10 C9A 108.9(2)
N3 C10 C9B 109.7(3)
N3 C11 N2 117.95(17)
C1 C6 C7 118.85(18)
C2 C3 C4 120.86(19)
C3 C2 C1 121.00(19)
C4 C5 C6 120.64(19)
C5 C4 C3 119.10(19)
C5 C6 C1 120.68(18)
C5 C6 C7 120.46(18)
C6 C1 C2 117.55(18)
C7 N2 C8 117.76(17)
C8 C9A C10 110.9(3)
C8 C9B C10 111.8(5)
C9A C8 N2 112.5(2)
C9A C10 C9B 43.3(3)
C9B C8 N2 117.9(3)
C9B C8 C9A 47.8(4)
C11 N1 C1 117.67(16)
C11 N2 C7 122.29(16)
C11 N2 C8 119.95(17)
C11 N3 C10 125.82(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.225(2)
N1 C1 1.377(2)
N1 C11 1.316(2)
N2 C7 1.395(3)
N2 C8 1.471(3)
N2 C11 1.391(2)
N3 C10 1.458(3)
N3 C11 1.338(3)
C1 C2 1.408(3)
C1 C6 1.407(3)
C2 C3 1.376(3)
C3 C4 1.403(3)
C4 C5 1.372(3)
C5 C6 1.403(3)
C6 C7 1.454(3)
C8 C9A 1.435(4)
C8 C9B 1.383(7)
C9A C10 1.529(4)
C9B C10 1.563(7)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 N1 0.89(2) 2.12(3) 3.006(2) 176(2) 3_666
