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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Tarun Sarkar'
_publ_contact_author_email       TKSR@CHEM.IITKGP.ERNET.IN

_publ_section_title              
;
Gold and Palladium Combined for the
Sonogashira-type Cross-coupling of Arenediazonium Salts
;
loop_
_publ_author_name
'Tarun Sarkar'
'Biswajit Panda'

# Attachment 'cif_file_of_compound_6.cif'

data_tksbp715u_0m
_database_code_depnum_ccdc_archive 'CCDC 753368'
#TrackingRef 'cif_file_of_compound_6.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9.14 N2.29 O4.57'
_chemical_formula_weight         306.54

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   'I 2/a'

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

_cell_length_a                   13.0640(10)
_cell_length_b                   12.9928(10)
_cell_length_c                   14.0524(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.245(6)
_cell_angle_gamma                90.00
_cell_volume                     2375.2(3)
_cell_formula_units_Z            7
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17240
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         31.73
_reflns_number_total             3627
_reflns_number_gt                1745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0534P)^2^+1.2718P] 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         3627
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003

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
C5 C 0.12892(13) 0.86580(13) 0.12086(11) 0.0440(4) Uani 1 1 d . . .
C4 C 0.13001(14) 0.76747(14) 0.16406(12) 0.0473(4) Uani 1 1 d . . .
H4 H 0.1360 0.7595 0.2301 0.057 Uiso 1 1 calc R . .
C6 C 0.12135(15) 0.87531(15) 0.01992(12) 0.0512(5) Uani 1 1 d . . .
O1 O 0.14251(13) 0.93620(11) 0.31360(9) 0.0735(5) Uani 1 1 d . . .
O2 O 0.12902(12) 1.02900(10) 0.07722(8) 0.0644(4) Uani 1 1 d . . .
C7 C 0.13239(14) 0.96575(14) 0.15317(12) 0.0488(5) Uani 1 1 d . . .
C8 C 0.13610(15) 1.00399(15) 0.25320(12) 0.0508(5) Uani 1 1 d . . .
N2 N 0.11981(14) 0.58243(13) 0.14631(13) 0.0655(5) Uani 1 1 d . . .
C1 C 0.11335(16) 0.78662(17) -0.03979(13) 0.0608(5) Uani 1 1 d . . .
H1 H 0.1083 0.7926 -0.1060 0.073 Uiso 1 1 calc R . .
C3 C 0.12186(14) 0.68592(14) 0.10453(13) 0.0498(5) Uani 1 1 d . . .
N1 N 0.12193(15) 0.97276(14) -0.00791(11) 0.0689(5) Uani 1 1 d . . .
C9 C 0.13157(14) 1.11410(14) 0.27893(13) 0.0496(5) Uani 1 1 d . . .
O3 O 0.12483(14) 0.57361(11) 0.23320(11) 0.0771(5) Uani 1 1 d . . .
C14 C 0.14607(16) 1.13907(17) 0.37579(14) 0.0628(6) Uani 1 1 d . . .
H14 H 0.1578 1.0873 0.4212 0.075 Uiso 1 1 calc R . .
C10 C 0.11295(16) 1.19370(15) 0.21309(15) 0.0593(5) Uani 1 1 d . . .
H10 H 0.1025 1.1787 0.1482 0.071 Uiso 1 1 calc R . .
C2 C 0.11336(16) 0.69383(16) 0.00278(13) 0.0586(5) Uani 1 1 d . . .
H2 H 0.1078 0.6345 -0.0343 0.070 Uiso 1 1 calc R . .
O4 O 0.11259(17) 0.50905(13) 0.09185(13) 0.1041(7) Uani 1 1 d . . .
C13 C 0.14300(17) 1.24078(19) 0.40431(17) 0.0736(7) Uani 1 1 d . . .
H13 H 0.1529 1.2569 0.4690 0.088 Uiso 1 1 calc R . .
C11 C 0.10988(17) 1.29453(17) 0.24340(18) 0.0702(6) Uani 1 1 d . . .
H11 H 0.0970 1.3469 0.1987 0.084 Uiso 1 1 calc R . .
C12 C 0.12553(16) 1.31840(19) 0.33841(19) 0.0744(7) Uani 1 1 d . . .
H12 H 0.1243 1.3866 0.3583 0.089 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
C5 0.0485(11) 0.0516(10) 0.0323(9) 0.0019(7) 0.0061(7) 0.0035(8)
C4 0.0545(11) 0.0528(11) 0.0346(9) 0.0025(7) 0.0047(8) 0.0050(8)
C6 0.0625(12) 0.0560(11) 0.0356(9) 0.0039(8) 0.0068(8) 0.0043(9)
O1 0.1273(14) 0.0564(8) 0.0373(7) 0.0058(6) 0.0102(8) -0.0002(8)
O2 0.1036(12) 0.0528(8) 0.0377(7) 0.0066(6) 0.0117(7) 0.0007(7)
C7 0.0622(12) 0.0479(10) 0.0368(9) 0.0056(7) 0.0077(8) 0.0017(9)
C8 0.0629(12) 0.0523(10) 0.0379(9) 0.0030(8) 0.0074(8) -0.0019(9)
N2 0.0833(13) 0.0517(10) 0.0614(11) -0.0025(9) 0.0072(9) 0.0105(9)
C1 0.0766(14) 0.0746(14) 0.0316(9) -0.0041(9) 0.0064(9) 0.0081(11)
C3 0.0537(12) 0.0497(10) 0.0463(10) -0.0001(8) 0.0067(8) 0.0064(8)
N1 0.1073(15) 0.0655(11) 0.0348(8) 0.0065(8) 0.0109(8) 0.0050(10)
C9 0.0505(11) 0.0523(10) 0.0469(10) -0.0040(8) 0.0094(8) -0.0025(8)
O3 0.1129(13) 0.0586(9) 0.0606(9) 0.0106(7) 0.0126(8) 0.0120(9)
C14 0.0688(14) 0.0678(14) 0.0518(11) -0.0094(10) 0.0054(10) 0.0012(11)
C10 0.0690(14) 0.0527(12) 0.0570(12) 0.0009(9) 0.0109(10) 0.0012(10)
C2 0.0707(14) 0.0615(12) 0.0437(10) -0.0128(9) 0.0055(9) 0.0079(10)
O4 0.179(2) 0.0517(9) 0.0806(12) -0.0124(9) 0.0063(12) 0.0057(11)
C13 0.0671(15) 0.0861(17) 0.0676(14) -0.0312(13) 0.0065(11) -0.0018(12)
C11 0.0745(15) 0.0513(12) 0.0865(17) -0.0018(11) 0.0159(12) 0.0019(11)
C12 0.0625(15) 0.0604(14) 0.1019(19) -0.0226(13) 0.0164(13) -0.0047(11)

_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
C5 C7 1.375(2) . ?
C5 C4 1.414(2) . ?
C5 C6 1.418(2) . ?
C4 C3 1.348(2) . ?
C6 N1 1.325(2) . ?
C6 C1 1.424(3) . ?
O1 C8 1.221(2) . ?
O2 C7 1.345(2) . ?
O2 N1 1.3976(19) . ?
C7 C8 1.488(2) . ?
C8 C9 1.478(3) . ?
N2 O3 1.222(2) . ?
N2 O4 1.221(2) . ?
N2 C3 1.468(3) . ?
C1 C2 1.346(3) . ?
C3 C2 1.428(2) . ?
C9 C10 1.394(3) . ?
C9 C14 1.395(3) . ?
C14 C13 1.383(3) . ?
C10 C11 1.379(3) . ?
C13 C12 1.374(3) . ?
C11 C12 1.368(3) . ?

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 C5 C4 135.47(16) . . ?
C7 C5 C6 104.19(15) . . ?
C4 C5 C6 120.34(16) . . ?
C3 C4 C5 116.53(16) . . ?
N1 C6 C5 112.12(16) . . ?
N1 C6 C1 126.97(17) . . ?
C5 C6 C1 120.90(17) . . ?
C7 O2 N1 110.77(13) . . ?
O2 C7 C5 108.51(14) . . ?
O2 C7 C8 122.81(16) . . ?
C5 C7 C8 128.66(15) . . ?
O1 C8 C9 122.00(16) . . ?
O1 C8 C7 114.22(17) . . ?
C9 C8 C7 123.77(15) . . ?
O3 N2 O4 123.18(19) . . ?
O3 N2 C3 118.95(17) . . ?
O4 N2 C3 117.88(18) . . ?
C2 C1 C6 117.78(17) . . ?
C4 C3 C2 124.01(18) . . ?
C4 C3 N2 118.35(17) . . ?
C2 C3 N2 117.63(17) . . ?
C6 N1 O2 104.39(14) . . ?
C10 C9 C14 118.35(18) . . ?
C10 C9 C8 124.34(17) . . ?
C14 C9 C8 117.31(17) . . ?
C13 C14 C9 120.0(2) . . ?
C11 C10 C9 120.5(2) . . ?
C1 C2 C3 120.43(18) . . ?
C12 C13 C14 120.9(2) . . ?
C12 C11 C10 120.7(2) . . ?
C11 C12 C13 119.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        31.73
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059