data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Jie Wu'
_publ_contact_author_email       'JIE WU@FUDAN.EDU.CN'

_publ_section_title              
;
Tandem Addition-Cyclization Reactions of
2-Alkynylbenzenamines with Isocyanates Catalyzed by PdCl2
;
loop_
_publ_author_name
'Jie Wu.'
'Qiuping Ding.'
'Bing Wang.'
'Shengqing Ye.'
'Haibo Zhou.'

# Attachment 'f80513b.cif'

data_f80513b
_database_code_depnum_ccdc_archive 'CCDC 695031'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36

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)/c

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

_cell_length_a                   10.974(5)
_cell_length_b                   14.927(6)
_cell_length_c                   9.978(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.267(6)
_cell_angle_gamma                90.00
_cell_volume                     1627.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    814
_cell_measurement_theta_min      2.310
_cell_measurement_theta_max      22.389

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9937
_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            6575
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0735
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2852
_reflns_number_gt                1546
_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^)+(0.0677P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_restrained_S_all      0.805
_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 0.08064(15) 0.26142(10) 0.85180(17) 0.0486(5) Uani 1 1 d . . .
H1A H 0.0572 0.2403 0.7735 0.058 Uiso 1 1 calc R . .
N2 N -0.08059(15) 0.17631(11) 0.91561(16) 0.0504(5) Uani 1 1 d . . .
O1 O 0.01678(13) 0.27720(10) 1.06193(15) 0.0625(4) Uani 1 1 d . . .
C1 C 0.18959(17) 0.31247(12) 0.8619(2) 0.0472(5) Uani 1 1 d . . .
C2 C 0.2619(2) 0.30806(15) 0.7565(2) 0.0609(6) Uani 1 1 d . . .
H2A H 0.2373 0.2727 0.6821 0.073 Uiso 1 1 calc R . .
C3 C 0.3701(2) 0.35521(17) 0.7595(3) 0.0724(7) Uani 1 1 d . . .
H3A H 0.4173 0.3519 0.6869 0.087 Uiso 1 1 calc R . .
C4 C 0.4081(2) 0.40660(16) 0.8681(3) 0.0727(7) Uani 1 1 d . . .
H4A H 0.4816 0.4379 0.8710 0.087 Uiso 1 1 calc R . .
C5 C 0.3364(2) 0.41142(16) 0.9729(3) 0.0711(7) Uani 1 1 d . . .
H5A H 0.3622 0.4464 1.0473 0.085 Uiso 1 1 calc R . .
C6 C 0.22708(19) 0.36597(14) 0.9713(2) 0.0585(6) Uani 1 1 d . . .
H6A H 0.1790 0.3711 1.0430 0.070 Uiso 1 1 calc R . .
C7 C 0.00943(18) 0.24204(13) 0.9508(2) 0.0478(5) Uani 1 1 d . . .
C8 C -0.20379(19) 0.19059(14) 0.9364(2) 0.0532(6) Uani 1 1 d . . .
C9 C -0.2570(2) 0.25171(15) 1.0176(2) 0.0651(7) Uani 1 1 d . . .
H9A H -0.2096 0.2926 1.0699 0.078 Uiso 1 1 calc R . .
C10 C -0.3826(2) 0.24989(18) 1.0182(3) 0.0800(8) Uani 1 1 d . . .
H10A H -0.4207 0.2898 1.0726 0.096 Uiso 1 1 calc R . .
C11 C -0.4534(2) 0.1892(2) 0.9385(3) 0.0835(8) Uani 1 1 d . . .
H11A H -0.5381 0.1899 0.9396 0.100 Uiso 1 1 calc R . .
C12 C -0.4006(2) 0.12847(19) 0.8585(3) 0.0782(8) Uani 1 1 d . . .
H12A H -0.4487 0.0881 0.8059 0.094 Uiso 1 1 calc R . .
C13 C -0.2734(2) 0.12818(15) 0.8573(2) 0.0598(6) Uani 1 1 d . . .
C14 C -0.1899(2) 0.07390(16) 0.7923(2) 0.0638(6) Uani 1 1 d . . .
H14A H -0.2113 0.0268 0.7337 0.077 Uiso 1 1 calc R . .
C15 C -0.07407(19) 0.10189(14) 0.8294(2) 0.0529(6) Uani 1 1 d . . .
C16 C 0.0404(2) 0.05607(14) 0.8064(2) 0.0550(6) Uani 1 1 d . . .
C17 C 0.0433(3) 0.00065(16) 0.6954(3) 0.0743(7) Uani 1 1 d . . .
H17A H -0.0242 -0.0020 0.6319 0.089 Uiso 1 1 calc R . .
C18 C 0.1447(3) -0.05021(17) 0.6783(4) 0.0967(10) Uani 1 1 d . . .
H18A H 0.1442 -0.0881 0.6043 0.116 Uiso 1 1 calc R . .
C19 C 0.2461(3) -0.0463(2) 0.7676(4) 0.1030(11) Uani 1 1 d . . .
H19A H 0.3147 -0.0806 0.7544 0.124 Uiso 1 1 calc R . .
C20 C 0.2455(3) 0.0085(2) 0.8764(3) 0.0917(9) Uani 1 1 d . . .
H20A H 0.3148 0.0122 0.9372 0.110 Uiso 1 1 calc R . .
C21 C 0.1432(2) 0.05878(15) 0.8978(2) 0.0689(7) Uani 1 1 d . . .
H21A H 0.1434 0.0946 0.9740 0.083 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 0.0477(10) 0.0586(11) 0.0403(10) -0.0037(8) 0.0078(8) -0.0093(8)
N2 0.0461(11) 0.0557(11) 0.0509(11) -0.0021(9) 0.0118(8) -0.0059(8)
O1 0.0624(10) 0.0836(11) 0.0420(10) -0.0077(8) 0.0074(8) -0.0084(8)
C1 0.0402(12) 0.0489(12) 0.0521(14) 0.0024(10) 0.0019(11) -0.0011(9)
C2 0.0519(14) 0.0761(16) 0.0563(15) -0.0089(12) 0.0134(12) -0.0059(12)
C3 0.0508(15) 0.0885(18) 0.0817(19) -0.0028(15) 0.0258(13) -0.0063(13)
C4 0.0427(14) 0.0785(17) 0.097(2) -0.0032(16) 0.0061(15) -0.0114(12)
C5 0.0584(16) 0.0715(16) 0.0818(19) -0.0139(14) -0.0014(14) -0.0113(13)
C6 0.0528(14) 0.0640(14) 0.0586(15) -0.0045(12) 0.0049(11) -0.0063(11)
C7 0.0455(13) 0.0546(13) 0.0429(14) 0.0019(11) 0.0029(11) 0.0004(10)
C8 0.0472(13) 0.0616(14) 0.0530(14) 0.0089(11) 0.0156(11) -0.0001(11)
C9 0.0585(15) 0.0701(16) 0.0689(17) 0.0057(13) 0.0174(13) 0.0025(11)
C10 0.0630(18) 0.095(2) 0.086(2) 0.0116(16) 0.0285(15) 0.0168(15)
C11 0.0450(15) 0.118(2) 0.089(2) 0.0212(18) 0.0131(15) 0.0027(16)
C12 0.0551(16) 0.103(2) 0.0772(19) 0.0078(16) 0.0089(14) -0.0112(14)
C13 0.0488(14) 0.0737(15) 0.0578(15) 0.0093(12) 0.0096(12) -0.0082(12)
C14 0.0631(16) 0.0727(16) 0.0561(15) -0.0057(12) 0.0077(12) -0.0168(13)
C15 0.0583(14) 0.0529(13) 0.0486(14) -0.0001(10) 0.0104(11) -0.0078(11)
C16 0.0612(15) 0.0490(13) 0.0572(15) 0.0041(11) 0.0177(12) -0.0045(11)
C17 0.0834(18) 0.0619(16) 0.0819(19) -0.0097(13) 0.0302(15) -0.0108(13)
C18 0.120(3) 0.0590(17) 0.121(3) -0.0093(17) 0.067(2) 0.0007(18)
C19 0.103(3) 0.080(2) 0.136(3) 0.032(2) 0.064(2) 0.0308(19)
C20 0.0758(19) 0.095(2) 0.107(3) 0.036(2) 0.0215(18) 0.0216(17)
C21 0.0720(17) 0.0699(16) 0.0658(17) 0.0100(13) 0.0121(14) 0.0089(13)

_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 1.346(3) . ?
N1 C1 1.414(2) . ?
N1 H1A 0.8600 . ?
N2 C8 1.403(3) . ?
N2 C15 1.411(3) . ?
N2 C7 1.414(2) . ?
O1 C7 1.223(2) . ?
C1 C2 1.376(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C8 C9 1.384(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.380(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.394(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.398(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.423(3) . ?
C14 C15 1.357(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.467(3) . ?
C16 C21 1.384(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.370(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.362(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.359(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

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 127.44(18) . . ?
C7 N1 H1A 116.3 . . ?
C1 N1 H1A 116.3 . . ?
C8 N2 C15 108.25(16) . . ?
C8 N2 C7 121.26(17) . . ?
C15 N2 C7 128.64(18) . . ?
C2 C1 C6 118.70(19) . . ?
C2 C1 N1 117.58(18) . . ?
C6 C1 N1 123.7(2) . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 H6A 120.4 . . ?
C1 C6 H6A 120.4 . . ?
O1 C7 N1 125.37(19) . . ?
O1 C7 N2 120.6(2) . . ?
N1 C7 N2 113.99(18) . . ?
C9 C8 C13 122.1(2) . . ?
C9 C8 N2 130.6(2) . . ?
C13 C8 N2 107.37(19) . . ?
C10 C9 C8 117.7(2) . . ?
C10 C9 H9A 121.2 . . ?
C8 C9 H9A 121.2 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 C14 133.7(2) . . ?
C8 C13 C14 107.16(19) . . ?
C15 C14 C13 109.0(2) . . ?
C15 C14 H14A 125.5 . . ?
C13 C14 H14A 125.5 . . ?
C14 C15 N2 108.07(19) . . ?
C14 C15 C16 127.5(2) . . ?
N2 C15 C16 123.68(18) . . ?
C21 C16 C17 117.9(2) . . ?
C21 C16 C15 122.8(2) . . ?
C17 C16 C15 119.1(2) . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18A 119.4 . . ?
C17 C18 H18A 119.4 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21A 119.8 . . ?
C16 C21 H21A 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041