# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Li, Jin-Heng'
'Deng, Guo-Bo'
'Wang, Zhi-Qiang'
'Song, Ren-Jie'
'Zhou, Ming-Bo'
'Wei, Wen-Ting'
'Xie, Peng'

_publ_contact_author_name        'Li, Jin-Heng'
_publ_contact_author_email       jhli@hunnu.edu.cn

_publ_section_title              
;
Synthesis of 3-(Aminomethylene)-2-oxoindolines by Palladium-Catalyzed 
Annulation of 3-Chloro-2-iodo-N-arylacrylamides with Amides or Amines
;

data_cd20194
_database_code_depnum_ccdc_archive 'CCDC 822997'
#TrackingRef 'cd20194.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.5014(8)
_cell_length_b                   10.8725(13)
_cell_length_c                   19.629(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.648(2)
_cell_angle_gamma                90.00
_cell_volume                     1380.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2468
_cell_measurement_theta_min      5.607
_cell_measurement_theta_max      55.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3181
_exptl_absorpt_correction_T_max  1.0000
_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            7944
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2993
_reflns_number_gt                2196
_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^)+(0.0776P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
O1 O 0.72528(19) 0.61245(11) 0.15258(6) 0.0595(4) Uani 1 1 d . . .
O2 O 0.3757(2) 1.01251(12) 0.09588(7) 0.0696(4) Uani 1 1 d . . .
N1 N 1.0141(2) 0.58545(12) 0.09458(6) 0.0433(3) Uani 1 1 d . . .
N2 N 0.5286(2) 0.82952(13) 0.11677(6) 0.0440(3) Uani 1 1 d . . .
C1 C 0.8396(3) 0.64599(14) 0.10971(7) 0.0432(4) Uani 1 1 d . . .
C2 C 0.8195(2) 0.75622(13) 0.06587(7) 0.0379(4) Uani 1 1 d . . .
C3 C 0.9905(2) 0.75158(13) 0.02328(7) 0.0382(4) Uani 1 1 d . . .
C4 C 1.1048(2) 0.64654(14) 0.04255(7) 0.0395(4) Uani 1 1 d . . .
C5 C 1.2805(2) 0.61488(16) 0.01226(8) 0.0500(4) Uani 1 1 d . . .
H5 H 1.3557 0.5446 0.0254 0.060 Uiso 1 1 calc R . .
C6 C 1.3401(3) 0.69150(17) -0.03828(8) 0.0561(5) Uani 1 1 d . . .
H6 H 1.4570 0.6720 -0.0598 0.067 Uiso 1 1 calc R . .
C7 C 1.2301(3) 0.79632(17) -0.05759(8) 0.0565(5) Uani 1 1 d . . .
H7 H 1.2747 0.8468 -0.0915 0.068 Uiso 1 1 calc R . .
C8 C 1.0532(3) 0.82743(15) -0.02698(8) 0.0475(4) Uani 1 1 d . . .
H8 H 0.9787 0.8980 -0.0402 0.057 Uiso 1 1 calc R . .
C9 C 0.6723(2) 0.84137(14) 0.07075(7) 0.0417(4) Uani 1 1 d . . .
H9 H 0.6678 0.9098 0.0423 0.050 Uiso 1 1 calc R . .
C10 C 0.3837(2) 0.91631(15) 0.12715(8) 0.0452(4) Uani 1 1 d . . .
C11 C 0.2366(2) 0.88549(15) 0.17850(7) 0.0450(4) Uani 1 1 d . . .
C12 C 0.0795(3) 0.96923(18) 0.18645(8) 0.0549(5) Uani 1 1 d . . .
H12 H 0.0715 1.0415 0.1609 0.066 Uiso 1 1 calc R . .
C13 C -0.0646(3) 0.9462(2) 0.23182(8) 0.0657(6) Uani 1 1 d . . .
H13 H -0.1697 1.0027 0.2366 0.079 Uiso 1 1 calc R . .
C14 C -0.0534(3) 0.8405(2) 0.26979(9) 0.0688(6) Uani 1 1 d . . .
H14 H -0.1513 0.8249 0.3002 0.083 Uiso 1 1 calc R . .
C15 C 0.1017(3) 0.75784(19) 0.26302(9) 0.0701(6) Uani 1 1 d . . .
H15 H 0.1099 0.6865 0.2893 0.084 Uiso 1 1 calc R . .
C16 C 0.2467(3) 0.77962(17) 0.21729(9) 0.0576(5) Uani 1 1 d . . .
H16 H 0.3512 0.7227 0.2127 0.069 Uiso 1 1 calc R . .
C17 C 1.0943(3) 0.47574(16) 0.12954(9) 0.0611(5) Uani 1 1 d . . .
H17A H 1.0083 0.4543 0.1648 0.092 Uiso 1 1 calc R . .
H17B H 1.2326 0.4908 0.1497 0.092 Uiso 1 1 calc R . .
H17C H 1.0952 0.4093 0.0974 0.092 Uiso 1 1 calc R . .
H2 H 0.542(2) 0.7617(15) 0.1410(7) 0.049(5) Uiso 1 1 d . . .

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
O1 0.0622(9) 0.0654(8) 0.0535(7) 0.0149(6) 0.0201(6) 0.0021(6)
O2 0.0691(9) 0.0558(8) 0.0895(9) 0.0120(7) 0.0352(8) 0.0143(7)
N1 0.0474(8) 0.0422(7) 0.0398(6) 0.0030(5) 0.0018(6) 0.0066(6)
N2 0.0399(8) 0.0474(8) 0.0462(7) -0.0009(6) 0.0114(6) 0.0046(6)
C1 0.0450(10) 0.0473(9) 0.0373(7) -0.0007(7) 0.0038(7) -0.0006(7)
C2 0.0366(9) 0.0411(8) 0.0362(7) -0.0016(6) 0.0046(6) 0.0000(6)
C3 0.0354(8) 0.0412(8) 0.0381(7) -0.0056(6) 0.0044(6) 0.0001(6)
C4 0.0389(9) 0.0429(8) 0.0360(7) -0.0063(6) 0.0002(6) 0.0022(6)
C5 0.0436(10) 0.0570(10) 0.0495(9) -0.0079(8) 0.0046(7) 0.0121(8)
C6 0.0419(10) 0.0732(12) 0.0554(9) -0.0118(9) 0.0153(8) 0.0055(9)
C7 0.0587(12) 0.0611(11) 0.0533(9) -0.0042(8) 0.0227(9) -0.0063(9)
C8 0.0522(10) 0.0435(9) 0.0486(8) 0.0012(7) 0.0141(7) 0.0036(7)
C9 0.0414(9) 0.0437(9) 0.0410(8) -0.0021(6) 0.0085(7) -0.0007(7)
C10 0.0426(10) 0.0453(9) 0.0485(9) -0.0072(7) 0.0091(7) 0.0008(7)
C11 0.0385(9) 0.0540(10) 0.0430(8) -0.0147(7) 0.0074(7) -0.0029(7)
C12 0.0503(11) 0.0694(12) 0.0456(8) -0.0120(8) 0.0070(7) 0.0086(9)
C13 0.0491(12) 0.1014(16) 0.0477(9) -0.0241(10) 0.0109(8) 0.0099(10)
C14 0.0594(13) 0.1004(16) 0.0498(10) -0.0199(11) 0.0216(9) -0.0146(11)
C15 0.0773(15) 0.0680(13) 0.0696(12) -0.0049(10) 0.0298(11) -0.0122(11)
C16 0.0576(12) 0.0541(11) 0.0643(10) -0.0074(9) 0.0219(9) -0.0020(9)
C17 0.0731(13) 0.0529(11) 0.0552(9) 0.0092(8) -0.0048(9) 0.0142(9)

_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
O1 C1 1.2314(17) . ?
O2 C10 1.2112(19) . ?
N1 C1 1.369(2) . ?
N1 C4 1.3966(19) . ?
N1 C17 1.448(2) . ?
N2 C10 1.363(2) . ?
N2 C9 1.3677(18) . ?
N2 H2 0.877(16) . ?
C1 C2 1.474(2) . ?
C2 C9 1.342(2) . ?
C2 C3 1.4562(19) . ?
C3 C8 1.378(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.494(2) . ?
C11 C16 1.378(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 N1 C4 110.41(13) . . ?
C1 N1 C17 124.10(13) . . ?
C4 N1 C17 125.47(14) . . ?
C10 N2 C9 124.09(15) . . ?
C10 N2 H2 122.2(10) . . ?
C9 N2 H2 113.7(10) . . ?
O1 C1 N1 125.08(15) . . ?
O1 C1 C2 127.95(15) . . ?
N1 C1 C2 106.97(13) . . ?
C9 C2 C3 130.94(14) . . ?
C9 C2 C1 122.84(14) . . ?
C3 C2 C1 106.15(13) . . ?
C8 C3 C4 119.81(13) . . ?
C8 C3 C2 133.36(14) . . ?
C4 C3 C2 106.82(12) . . ?
C5 C4 C3 121.89(14) . . ?
C5 C4 N1 128.50(14) . . ?
C3 C4 N1 109.61(12) . . ?
C6 C5 C4 117.46(15) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C7 C6 C5 121.47(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.73(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 118.63(15) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C2 C9 N2 121.36(14) . . ?
C2 C9 H9 119.3 . . ?
N2 C9 H9 119.3 . . ?
O2 C10 N2 121.21(15) . . ?
O2 C10 C11 122.47(15) . . ?
N2 C10 C11 116.32(15) . . ?
C16 C11 C12 118.78(15) . . ?
C16 C11 C10 124.11(15) . . ?
C12 C11 C10 117.10(16) . . ?
C13 C12 C11 120.54(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.11(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.97(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.15(18) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 178.60(14) . . . . ?
C17 N1 C1 O1 -3.1(3) . . . . ?
C4 N1 C1 C2 -1.87(17) . . . . ?
C17 N1 C1 C2 176.45(14) . . . . ?
O1 C1 C2 C9 4.2(3) . . . . ?
N1 C1 C2 C9 -175.31(14) . . . . ?
O1 C1 C2 C3 -178.57(15) . . . . ?
N1 C1 C2 C3 1.91(16) . . . . ?
C9 C2 C3 C8 -3.2(3) . . . . ?
C1 C2 C3 C8 179.92(16) . . . . ?
C9 C2 C3 C4 175.64(16) . . . . ?
C1 C2 C3 C4 -1.26(15) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C5 -179.47(13) . . . . ?
C8 C3 C4 N1 179.18(13) . . . . ?
C2 C3 C4 N1 0.17(16) . . . . ?
C1 N1 C4 C5 -179.29(15) . . . . ?
C17 N1 C4 C5 2.4(2) . . . . ?
C1 N1 C4 C3 1.10(17) . . . . ?
C17 N1 C4 C3 -177.19(14) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
N1 C4 C5 C6 -179.55(14) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C2 C3 C8 C7 179.00(15) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C3 C2 C9 N2 -177.40(14) . . . . ?
C1 C2 C9 N2 -0.9(2) . . . . ?
C10 N2 C9 C2 175.70(15) . . . . ?
C9 N2 C10 O2 -1.1(3) . . . . ?
C9 N2 C10 C11 178.58(13) . . . . ?
O2 C10 C11 C16 -176.90(16) . . . . ?
N2 C10 C11 C16 3.5(2) . . . . ?
O2 C10 C11 C12 3.8(2) . . . . ?
N2 C10 C11 C12 -175.86(14) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 C13 178.74(15) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C12 C11 C16 C15 0.2(3) . . . . ?
C10 C11 C16 C15 -179.07(15) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?

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
C13 H13 O1 0.93 2.54 3.158(2) 124.4 2
N2 H2 O1 0.877(16) 2.014(16) 2.7425(19) 139.7(13) .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038