# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Shengqing Ye.'
'Xiaodi Yang.'
'Jie Wu.'

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

_publ_section_title              
;
Silver triflate-catalyzed three-component
reaction of 2-alkynylbenzaldehyde, sulfonohydrazide,
and a,b-unsaturated carbonyl compound
;

# Attachment '5-3a.cif.txt'

data_091120wujie_0ma
_database_code_depnum_ccdc_archive 'CCDC 773018'
#TrackingRef '5-3a.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

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           Orthorhombic
_symmetry_space_group_name_H-M   Iba2

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

_cell_length_a                   18.132(3)
_cell_length_b                   24.803(4)
_cell_length_c                   7.2352(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3253.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2892
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      23.05

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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            8533
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.01
_reflns_number_total             2828
_reflns_number_gt                2202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0452P)^2^+0.5133P] 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       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(15)
_refine_ls_number_reflns         2828
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.09175(8) 0.25388(5) 0.1970(2) 0.0538(4) Uani 1 1 d . . .
C11 C 0.11022(10) 0.19989(7) 0.1764(3) 0.0532(4) Uani 1 1 d . . .
N2 N 0.01867(8) 0.26376(5) 0.1651(3) 0.0612(5) Uani 1 1 d . . .
C9 C 0.23734(11) 0.22621(8) 0.2477(3) 0.0604(5) Uani 1 1 d . . .
C1 C 0.11537(10) 0.35108(7) 0.2670(3) 0.0545(5) Uani 1 1 d . . .
O2 O -0.04714(8) 0.11031(5) 0.1030(3) 0.0814(5) Uani 1 1 d . . .
C6 C 0.15805(11) 0.39185(7) 0.1919(3) 0.0636(5) Uani 1 1 d . . .
H6 H 0.1980 0.3832 0.1171 0.076 Uiso 1 1 calc R . .
C8 C 0.21201(11) 0.28032(8) 0.2698(3) 0.0598(5) Uani 1 1 d . . .
H8 H 0.2458 0.3067 0.3038 0.072 Uiso 1 1 calc R . .
C7 C 0.14117(10) 0.29467(7) 0.2435(3) 0.0543(5) Uani 1 1 d . . .
C10 C 0.18700(10) 0.18545(7) 0.1993(3) 0.0566(5) Uani 1 1 d . . .
C15 C 0.21426(12) 0.13276(8) 0.1715(3) 0.0692(6) Uani 1 1 d . . .
H15 H 0.1821 0.1052 0.1386 0.083 Uiso 1 1 calc R . .
C16 C 0.04380(10) 0.17432(7) 0.1331(3) 0.0575(5) Uani 1 1 d . . .
C18 C 0.02578(12) 0.11710(8) 0.1085(3) 0.0655(6) Uani 1 1 d . . .
C14 C 0.28812(12) 0.12208(9) 0.1928(4) 0.0776(6) Uani 1 1 d . . .
H14 H 0.3055 0.0873 0.1726 0.093 Uiso 1 1 calc R . .
O1 O 0.06794(9) 0.07986(5) 0.0978(3) 0.0958(6) Uani 1 1 d . . .
C12 C 0.31230(11) 0.21321(9) 0.2711(3) 0.0691(6) Uani 1 1 d . . .
H12 H 0.3454 0.2400 0.3059 0.083 Uiso 1 1 calc R . .
C17 C -0.00882(11) 0.21551(7) 0.1288(3) 0.0633(5) Uani 1 1 d . . .
H17 H -0.0584 0.2096 0.1029 0.076 Uiso 1 1 calc R . .
C2 C 0.05498(11) 0.36448(7) 0.3756(3) 0.0613(5) Uani 1 1 d . . .
H2 H 0.0252 0.3375 0.4247 0.074 Uiso 1 1 calc R . .
C5 C 0.14191(11) 0.44521(8) 0.2268(4) 0.0754(7) Uani 1 1 d . . .
H5 H 0.1710 0.4723 0.1762 0.090 Uiso 1 1 calc R . .
C13 C 0.33693(12) 0.16214(10) 0.2437(3) 0.0771(7) Uani 1 1 d . . .
H13 H 0.3867 0.1541 0.2592 0.093 Uiso 1 1 calc R . .
C3 C 0.03914(12) 0.41816(8) 0.4109(4) 0.0705(6) Uani 1 1 d . . .
H3 H -0.0010 0.4271 0.4848 0.085 Uiso 1 1 calc R . .
C4 C 0.08251(13) 0.45814(8) 0.3372(4) 0.0768(7) Uani 1 1 d . . .
H4 H 0.0718 0.4941 0.3618 0.092 Uiso 1 1 calc R . .
C19 C -0.07319(13) 0.05495(8) 0.0921(5) 0.0911(8) Uani 1 1 d . . .
H19A H -0.0489 0.0331 0.1852 0.109 Uiso 1 1 calc R . .
H19B H -0.0620 0.0400 -0.0285 0.109 Uiso 1 1 calc R . .
C20 C -0.15220(13) 0.05487(10) 0.1223(6) 0.1130(11) Uani 1 1 d . . .
H20A H -0.1625 0.0663 0.2464 0.169 Uiso 1 1 calc R . .
H20B H -0.1711 0.0191 0.1039 0.169 Uiso 1 1 calc R . .
H20C H -0.1753 0.0791 0.0367 0.169 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 0.0634(9) 0.0472(8) 0.0508(9) 0.0013(7) -0.0014(8) 0.0088(7)
C11 0.0692(11) 0.0472(9) 0.0434(10) 0.0043(9) 0.0053(9) 0.0098(8)
N2 0.0628(10) 0.0516(8) 0.0692(13) -0.0013(9) -0.0091(9) 0.0104(7)
C9 0.0677(12) 0.0694(12) 0.0440(11) 0.0009(9) 0.0028(9) 0.0118(10)
C1 0.0638(11) 0.0500(10) 0.0498(11) -0.0018(9) -0.0039(9) 0.0043(8)
O2 0.0787(10) 0.0518(8) 0.1139(15) -0.0030(8) 0.0038(10) -0.0006(6)
C6 0.0683(11) 0.0568(11) 0.0657(13) -0.0010(11) 0.0005(10) -0.0011(8)
C8 0.0669(12) 0.0614(11) 0.0509(12) -0.0050(10) -0.0010(10) 0.0043(9)
C7 0.0664(11) 0.0505(10) 0.0459(12) -0.0010(8) -0.0001(9) 0.0046(9)
C10 0.0680(11) 0.0575(10) 0.0442(10) 0.0048(9) 0.0062(9) 0.0150(9)
C15 0.0806(13) 0.0605(11) 0.0665(14) 0.0031(11) 0.0114(12) 0.0158(10)
C16 0.0717(11) 0.0468(9) 0.0539(12) 0.0000(9) 0.0019(9) 0.0062(8)
C18 0.0760(14) 0.0541(11) 0.0664(15) -0.0016(10) 0.0053(12) 0.0055(9)
C14 0.0832(15) 0.0726(13) 0.0769(16) 0.0061(13) 0.0119(14) 0.0325(12)
O1 0.0878(10) 0.0506(8) 0.1491(18) -0.0124(10) 0.0057(11) 0.0076(7)
C12 0.0677(13) 0.0845(15) 0.0551(12) -0.0022(12) 0.0006(11) 0.0151(11)
C17 0.0689(11) 0.0528(10) 0.0682(14) -0.0017(10) -0.0058(11) 0.0054(9)
C2 0.0688(12) 0.0556(11) 0.0595(13) 0.0016(10) -0.0002(10) 0.0096(9)
C5 0.0768(14) 0.0546(12) 0.095(2) 0.0027(12) -0.0060(13) -0.0050(10)
C13 0.0720(13) 0.0998(18) 0.0595(15) 0.0047(13) 0.0046(11) 0.0279(13)
C3 0.0744(13) 0.0627(13) 0.0746(16) -0.0080(11) -0.0002(11) 0.0162(10)
C4 0.0833(15) 0.0507(11) 0.0964(19) -0.0110(12) -0.0149(14) 0.0094(11)
C19 0.0959(17) 0.0572(12) 0.120(2) -0.0017(15) 0.0084(16) -0.0087(11)
C20 0.0849(17) 0.0994(19) 0.155(3) -0.001(2) 0.0023(19) -0.0134(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 N2 1.367(2) . ?
N1 C11 1.388(2) . ?
N1 C7 1.393(2) . ?
C11 C16 1.397(3) . ?
C11 C10 1.447(3) . ?
N2 C17 1.323(2) . ?
C9 C12 1.407(3) . ?
C9 C10 1.406(3) . ?
C9 C8 1.427(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.485(2) . ?
O2 C18 1.333(2) . ?
O2 C19 1.454(2) . ?
C6 C5 1.379(3) . ?
C6 H6 0.9300 . ?
C8 C7 1.346(3) . ?
C8 H8 0.9300 . ?
C10 C15 1.412(2) . ?
C15 C14 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(2) . ?
C16 C18 1.467(2) . ?
C18 O1 1.201(2) . ?
C14 C13 1.380(3) . ?
C14 H14 0.9300 . ?
C12 C13 1.358(3) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C5 C4 1.379(3) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C19 C20 1.449(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
N2 N1 C11 112.86(14) . . ?
N2 N1 C7 122.29(13) . . ?
C11 N1 C7 124.85(15) . . ?
C16 C11 N1 104.71(15) . . ?
C16 C11 C10 137.98(16) . . ?
N1 C11 C10 117.29(16) . . ?
C17 N2 N1 103.69(13) . . ?
C12 C9 C10 119.48(18) . . ?
C12 C9 C8 120.86(19) . . ?
C10 C9 C8 119.65(17) . . ?
C6 C1 C2 119.22(17) . . ?
C6 C1 C7 117.85(17) . . ?
C2 C1 C7 122.60(18) . . ?
C18 O2 C19 116.28(16) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C7 C8 C9 122.68(18) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C7 N1 117.11(16) . . ?
C8 C7 C1 122.25(18) . . ?
N1 C7 C1 120.62(15) . . ?
C9 C10 C15 118.28(17) . . ?
C9 C10 C11 118.37(15) . . ?
C15 C10 C11 123.34(18) . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C11 C16 C17 105.17(15) . . ?
C11 C16 C18 131.18(16) . . ?
C17 C16 C18 123.52(17) . . ?
O1 C18 O2 122.14(18) . . ?
O1 C18 C16 127.57(19) . . ?
O2 C18 C16 110.27(16) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C13 C12 C9 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C9 C12 H12 119.5 . . ?
N2 C17 C16 113.55(17) . . ?
N2 C17 H17 123.2 . . ?
C16 C17 H17 123.2 . . ?
C1 C2 C3 119.85(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.28(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O2 C19 C20 108.31(19) . . ?
O2 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
O2 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.032