# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Qiu, Guanyinsheng'
'Liu, Gang'
'Pu, Shouzhi'
'Wu, Jie'

_publ_contact_author_name        'Dr Jie Wu'
_publ_contact_author_email       jie_wu@fudan.edu.cn

_publ_section_title              
;
A palladium-catalyzed three-component
reaction for the preparation of quinazolin-4(3H)-imines
;

# Attachment '- a11121c.cif'

data_a11121c
_database_code_depnum_ccdc_archive 'CCDC 860138'
#TrackingRef '- a11121c.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 N4'
_chemical_formula_weight         346.47

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.764(3)
_cell_length_b                   9.110(3)
_cell_length_c                   14.936(5)
_cell_angle_alpha                80.214(5)
_cell_angle_beta                 89.198(5)
_cell_angle_gamma                67.968(4)
_cell_volume                     963.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    742
_cell_measurement_theta_min      2.451
_cell_measurement_theta_max      27.313

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4034
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3350
_reflns_number_gt                2630
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1700P)^2^+0.0659P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.2408
_refine_ls_wR_factor_gt          0.2232
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.0717(3) 0.2063(2) 0.24799(12) 0.0385(5) Uani 1 1 d . . .
N2 N 0.2488(3) 0.2651(2) 0.35351(14) 0.0461(5) Uani 1 1 d . . .
N3 N -0.0542(3) 0.4376(2) 0.32178(14) 0.0467(6) Uani 1 1 d . . .
N4 N -0.0143(3) 0.2956(2) 0.08569(13) 0.0448(5) Uani 1 1 d . . .
C1 C 0.0362(3) 0.0663(3) 0.28897(15) 0.0376(5) Uani 1 1 d . . .
C2 C -0.0582(4) 0.0011(3) 0.23901(16) 0.0470(6) Uani 1 1 d . . .
H2 H -0.1011 0.0495 0.1793 0.056 Uiso 1 1 calc R . .
C3 C -0.0881(4) -0.1356(3) 0.27798(18) 0.0529(7) Uani 1 1 d . . .
H3 H -0.1515 -0.1778 0.2439 0.064 Uiso 1 1 calc R . .
C4 C -0.0264(4) -0.2101(3) 0.36572(18) 0.0503(7) Uani 1 1 d . . .
H4 H -0.0458 -0.3029 0.3909 0.060 Uiso 1 1 calc R . .
C5 C 0.0645(3) -0.1454(3) 0.41563(17) 0.0486(6) Uani 1 1 d . . .
H5 H 0.1057 -0.1942 0.4755 0.058 Uiso 1 1 calc R . .
C6 C 0.0961(3) -0.0082(3) 0.37825(16) 0.0444(6) Uani 1 1 d . . .
H6 H 0.1578 0.0342 0.4132 0.053 Uiso 1 1 calc R . .
C7 C 0.0827(3) 0.3097(3) 0.30865(16) 0.0402(6) Uani 1 1 d . . .
C8 C 0.4259(3) 0.1451(3) 0.33346(18) 0.0516(7) Uani 1 1 d . . .
H8A H 0.4455 0.1599 0.2688 0.062 Uiso 1 1 calc R . .
H8B H 0.4304 0.0367 0.3539 0.062 Uiso 1 1 calc R . .
C9 C 0.5658(4) 0.1769(4) 0.3856(3) 0.0793(10) Uani 1 1 d . . .
H9A H 0.6628 0.0762 0.4133 0.095 Uiso 1 1 calc R . .
H9B H 0.6227 0.2390 0.3454 0.095 Uiso 1 1 calc R . .
C10 C 0.4695(4) 0.2669(4) 0.4560(2) 0.0773(10) Uani 1 1 d . . .
H10A H 0.5282 0.3386 0.4689 0.093 Uiso 1 1 calc R . .
H10B H 0.4707 0.1941 0.5118 0.093 Uiso 1 1 calc R . .
C11 C 0.2750(3) 0.3603(3) 0.41750(18) 0.0509(7) Uani 1 1 d . . .
H11A H 0.1866 0.3700 0.4648 0.061 Uiso 1 1 calc R . .
H11B H 0.2610 0.4671 0.3866 0.061 Uiso 1 1 calc R . .
C12 C -0.2232(3) 0.4778(3) 0.27166(17) 0.0439(6) Uani 1 1 d . . .
C13 C -0.3846(4) 0.5917(3) 0.2972(2) 0.0548(7) Uani 1 1 d . . .
H13 H -0.3808 0.6364 0.3483 0.066 Uiso 1 1 calc R . .
C14 C -0.5497(4) 0.6384(3) 0.2472(2) 0.0640(8) Uani 1 1 d . . .
H14 H -0.6572 0.7132 0.2654 0.077 Uiso 1 1 calc R . .
C15 C -0.5573(4) 0.5749(4) 0.1701(2) 0.0642(8) Uani 1 1 d . . .
H15 H -0.6695 0.6062 0.1368 0.077 Uiso 1 1 calc R . .
C16 C -0.3969(3) 0.4646(3) 0.14301(18) 0.0521(7) Uani 1 1 d . . .
H16 H -0.4011 0.4234 0.0906 0.062 Uiso 1 1 calc R . .
C17 C -0.2300(3) 0.4147(3) 0.19311(16) 0.0422(6) Uani 1 1 d . . .
C18 C -0.0515(3) 0.3017(3) 0.16761(15) 0.0405(6) Uani 1 1 d . . .
C19 C 0.1674(3) 0.2068(3) 0.05062(16) 0.0472(6) Uani 1 1 d . . .
C20 C 0.1295(5) 0.2248(5) -0.0517(2) 0.0747(9) Uani 1 1 d . . .
H20A H 0.0432 0.1757 -0.0618 0.112 Uiso 1 1 calc R . .
H20B H 0.2439 0.1730 -0.0792 0.112 Uiso 1 1 calc R . .
H20C H 0.0776 0.3369 -0.0783 0.112 Uiso 1 1 calc R . .
C21 C 0.2938(4) 0.2965(4) 0.0637(2) 0.0647(8) Uani 1 1 d . . .
H21A H 0.2366 0.4064 0.0334 0.097 Uiso 1 1 calc R . .
H21B H 0.4114 0.2462 0.0385 0.097 Uiso 1 1 calc R . .
H21C H 0.3129 0.2934 0.1275 0.097 Uiso 1 1 calc R . .
C22 C 0.2603(4) 0.0302(3) 0.0928(2) 0.0688(9) Uani 1 1 d . . .
H22A H 0.2910 0.0205 0.1561 0.103 Uiso 1 1 calc R . .
H22B H 0.3718 -0.0182 0.0624 0.103 Uiso 1 1 calc R . .
H22C H 0.1769 -0.0235 0.0866 0.103 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0444(10) 0.0301(9) 0.0380(10) -0.0070(7) 0.0038(8) -0.0104(8)
N2 0.0467(11) 0.0376(10) 0.0508(12) -0.0144(9) -0.0009(9) -0.0094(9)
N3 0.0446(11) 0.0372(11) 0.0554(13) -0.0156(9) 0.0027(9) -0.0091(9)
N4 0.0534(12) 0.0394(11) 0.0390(11) -0.0056(8) 0.0047(9) -0.0154(9)
C1 0.0406(11) 0.0301(11) 0.0383(12) -0.0105(9) 0.0087(9) -0.0072(9)
C2 0.0647(15) 0.0462(13) 0.0339(12) -0.0087(10) 0.0067(10) -0.0247(12)
C3 0.0744(17) 0.0494(14) 0.0473(14) -0.0180(11) 0.0133(12) -0.0336(14)
C4 0.0610(15) 0.0333(12) 0.0542(15) -0.0080(10) 0.0168(12) -0.0155(11)
C5 0.0555(14) 0.0392(13) 0.0407(13) 0.0009(10) 0.0064(11) -0.0096(11)
C6 0.0474(13) 0.0409(13) 0.0409(13) -0.0098(10) 0.0036(10) -0.0113(11)
C7 0.0448(12) 0.0315(11) 0.0432(13) -0.0081(9) 0.0043(10) -0.0127(10)
C8 0.0477(13) 0.0456(14) 0.0519(15) -0.0115(11) 0.0020(11) -0.0056(12)
C9 0.0520(16) 0.087(2) 0.094(3) -0.039(2) 0.0003(16) -0.0106(17)
C10 0.0662(19) 0.078(2) 0.076(2) -0.0280(18) -0.0175(16) -0.0083(17)
C11 0.0539(14) 0.0485(14) 0.0522(15) -0.0166(11) 0.0011(11) -0.0181(12)
C12 0.0450(13) 0.0328(12) 0.0517(14) -0.0067(10) 0.0086(10) -0.0127(10)
C13 0.0522(14) 0.0400(13) 0.0635(17) -0.0122(12) 0.0103(12) -0.0069(12)
C14 0.0471(15) 0.0471(15) 0.081(2) -0.0041(14) 0.0151(14) -0.0029(12)
C15 0.0483(15) 0.0569(17) 0.074(2) 0.0016(15) -0.0032(13) -0.0106(13)
C16 0.0507(14) 0.0489(15) 0.0498(15) -0.0012(11) -0.0021(11) -0.0142(12)
C17 0.0443(12) 0.0336(11) 0.0438(13) -0.0002(9) 0.0049(10) -0.0120(10)
C18 0.0517(13) 0.0325(12) 0.0363(12) -0.0030(9) 0.0017(10) -0.0160(10)
C19 0.0549(14) 0.0466(14) 0.0398(13) -0.0095(10) 0.0085(10) -0.0183(12)
C20 0.077(2) 0.095(2) 0.0491(17) -0.0228(16) 0.0121(15) -0.0257(19)
C21 0.0698(18) 0.0649(18) 0.0625(18) -0.0138(14) 0.0148(14) -0.0281(15)
C22 0.0723(19) 0.0479(16) 0.078(2) -0.0168(14) 0.0308(16) -0.0125(14)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.438(3) . ?
N1 C1 1.439(3) . ?
N1 C18 1.472(3) . ?
N2 C7 1.347(3) . ?
N2 C11 1.459(3) . ?
N2 C8 1.465(3) . ?
N3 C7 1.291(3) . ?
N3 C12 1.411(3) . ?
N4 C18 1.259(3) . ?
N4 C19 1.479(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.485(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.467(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.493(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.392(3) . ?
C12 C17 1.402(3) . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.474(3) . ?
C19 C22 1.518(4) . ?
C19 C21 1.527(4) . ?
C19 C20 1.530(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 116.07(17) . . ?
C7 N1 C18 110.24(17) . . ?
C1 N1 C18 114.11(17) . . ?
C7 N2 C11 120.29(19) . . ?
C7 N2 C8 126.8(2) . . ?
C11 N2 C8 111.83(19) . . ?
C7 N3 C12 117.0(2) . . ?
C18 N4 C19 127.1(2) . . ?
C6 C1 C2 118.3(2) . . ?
C6 C1 N1 121.3(2) . . ?
C2 C1 N1 120.3(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N3 C7 N2 120.1(2) . . ?
N3 C7 N1 124.2(2) . . ?
N2 C7 N1 115.66(19) . . ?
N2 C8 C9 103.3(2) . . ?
N2 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
N2 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 107.8(3) . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 C11 105.2(3) . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
N2 C11 C10 103.6(2) . . ?
N2 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
N2 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C17 119.2(2) . . ?
C13 C12 N3 119.1(2) . . ?
C17 C12 N3 121.6(2) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.7(2) . . ?
C16 C17 C18 124.2(2) . . ?
C12 C17 C18 116.0(2) . . ?
N4 C18 N1 126.5(2) . . ?
N4 C18 C17 121.7(2) . . ?
N1 C18 C17 111.82(18) . . ?
N4 C19 C22 116.0(2) . . ?
N4 C19 C21 106.8(2) . . ?
C22 C19 C21 110.5(2) . . ?
N4 C19 C20 105.3(2) . . ?
C22 C19 C20 110.1(2) . . ?
C21 C19 C20 107.8(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.076