# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Yoshiaki Nakao'
_publ_contact_author_email       YOSHIAKINAKAO@NPC05.MBOX.MEDIA.KYOTO-U.AC.JP

_publ_section_title              
;
Nickel/AlMe2Cl-catalysed Carbocyanation of Alkynes
Using Arylacetonitriles
;
loop_
_publ_author_name
'Yoshiaki Nakao'
'Tamejiro Hiyama'
'Akira Yada'
'Tomoya Yukawa'

# Attachment '_Z_-3ac.cif'

data_1yda
_database_code_depnum_ccdc_archive 'CCDC 727199'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 N'
_chemical_formula_weight         295.37

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.1248(17)
_cell_length_b                   8.3530(8)
_cell_length_c                   25.014(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.290(2)
_cell_angle_gamma                90.00
_cell_volume                     3303.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3563
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.75

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      300(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 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8599
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3059
_reflns_number_gt                2441
_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^)+(0.0603P)^2^+0.4979P] 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         3059
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C2 C 0.08806(8) 0.59699(15) 0.08135(5) 0.0550(3) Uani 1 1 d . . .
C3 C 0.13924(8) 0.72859(15) 0.06389(5) 0.0547(3) Uani 1 1 d . . .
C9 C 0.11620(8) 0.45394(15) 0.10320(5) 0.0552(3) Uani 1 1 d . . .
C17 C 0.25777(8) 0.37150(14) 0.16218(5) 0.0536(3) Uani 1 1 d . . .
C7 C 0.26263(9) 0.89663(18) 0.07791(6) 0.0696(4) Uani 1 1 d . . .
H7 H 0.3150 0.9242 0.0987 0.084 Uiso 1 1 calc R . .
C1 C -0.00149(10) 0.63007(17) 0.07043(6) 0.0640(4) Uani 1 1 d . . .
C10 C 0.05908(8) 0.34197(15) 0.12456(5) 0.0581(3) Uani 1 1 d . . .
C18 C 0.32487(9) 0.26517(16) 0.16986(6) 0.0652(4) Uani 1 1 d . . .
H18 H 0.3353 0.2053 0.1405 0.078 Uiso 1 1 calc R . .
C16 C 0.20532(9) 0.39685(17) 0.10568(5) 0.0619(4) Uani 1 1 d . . .
H16A H 0.2341 0.4741 0.0868 0.074 Uiso 1 1 calc R . .
H16B H 0.2031 0.2966 0.0859 0.074 Uiso 1 1 calc R . .
C11 C 0.00907(10) 0.39536(19) 0.16021(6) 0.0708(4) Uani 1 1 d . . .
H11 H 0.0113 0.5026 0.1704 0.085 Uiso 1 1 calc R . .
C8 C 0.21631(9) 0.77443(17) 0.09495(5) 0.0635(4) Uani 1 1 d . . .
H8 H 0.2371 0.7223 0.1277 0.076 Uiso 1 1 calc R . .
C6 C 0.23191(10) 0.97738(18) 0.03059(6) 0.0694(4) Uani 1 1 d . . .
H6 H 0.2632 1.0598 0.0193 0.083 Uiso 1 1 calc R . .
N1 N -0.07144(9) 0.66359(18) 0.05878(7) 0.0900(5) Uani 1 1 d . . .
C22 C 0.24433(10) 0.45671(18) 0.20676(5) 0.0675(4) Uani 1 1 d . . .
H22 H 0.1993 0.5282 0.2028 0.081 Uiso 1 1 calc R . .
C15 C 0.05498(10) 0.18049(18) 0.11049(7) 0.0751(4) Uani 1 1 d . . .
H15 H 0.0885 0.1407 0.0872 0.090 Uiso 1 1 calc R . .
C4 C 0.10885(9) 0.81272(18) 0.01642(6) 0.0677(4) Uani 1 1 d . . .
H4 H 0.0567 0.7856 -0.0047 0.081 Uiso 1 1 calc R . .
C5 C 0.15494(10) 0.9363(2) 0.00004(6) 0.0753(4) Uani 1 1 d . . .
H5 H 0.1336 0.9918 -0.0319 0.090 Uiso 1 1 calc R . .
C13 C -0.04780(13) 0.1349(3) 0.16613(9) 0.0986(7) Uani 1 1 d . . .
H13 H -0.0836 0.0655 0.1799 0.118 Uiso 1 1 calc R . .
C19 C 0.37630(10) 0.24677(19) 0.22027(7) 0.0777(4) Uani 1 1 d . . .
H19 H 0.4209 0.1744 0.2246 0.093 Uiso 1 1 calc R . .
C12 C -0.04387(11) 0.2926(2) 0.18084(7) 0.0869(5) Uani 1 1 d . . .
H12 H -0.0768 0.3307 0.2047 0.104 Uiso 1 1 calc R . .
C20 C 0.36269(10) 0.3332(2) 0.26384(7) 0.0789(5) Uani 1 1 d . . .
H20 H 0.3981 0.3211 0.2977 0.095 Uiso 1 1 calc R . .
C14 C 0.00101(13) 0.0792(2) 0.13109(9) 0.0973(6) Uani 1 1 d . . .
H14 H -0.0022 -0.0281 0.1210 0.117 Uiso 1 1 calc R . .
C21 C 0.29632(11) 0.4381(2) 0.25721(6) 0.0804(5) Uani 1 1 d . . .
H21 H 0.2862 0.4972 0.2868 0.097 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
C2 0.0586(8) 0.0539(7) 0.0528(7) -0.0010(5) 0.0118(6) -0.0076(6)
C3 0.0586(7) 0.0543(7) 0.0528(7) -0.0010(5) 0.0150(6) -0.0034(6)
C9 0.0646(8) 0.0524(7) 0.0484(6) -0.0046(5) 0.0104(6) -0.0077(6)
C17 0.0554(7) 0.0444(6) 0.0640(8) 0.0003(5) 0.0187(6) -0.0060(6)
C7 0.0651(9) 0.0692(9) 0.0735(9) -0.0031(7) 0.0110(7) -0.0175(7)
C1 0.0613(9) 0.0558(8) 0.0751(9) 0.0089(6) 0.0139(7) -0.0100(7)
C10 0.0636(8) 0.0515(7) 0.0543(7) 0.0029(6) 0.0000(6) -0.0095(6)
C18 0.0584(8) 0.0537(8) 0.0860(10) -0.0073(7) 0.0206(7) -0.0028(6)
C16 0.0723(9) 0.0567(8) 0.0598(8) -0.0048(6) 0.0204(6) 0.0001(7)
C11 0.0775(10) 0.0675(9) 0.0680(9) 0.0027(7) 0.0161(7) -0.0195(8)
C8 0.0678(8) 0.0632(8) 0.0576(7) 0.0031(6) 0.0073(6) -0.0104(7)
C6 0.0760(10) 0.0639(9) 0.0740(9) 0.0027(7) 0.0288(8) -0.0148(7)
N1 0.0652(9) 0.0836(10) 0.1223(12) 0.0231(8) 0.0209(8) -0.0052(7)
C22 0.0752(9) 0.0646(9) 0.0630(8) -0.0014(7) 0.0145(7) 0.0133(7)
C15 0.0795(10) 0.0535(8) 0.0835(10) 0.0006(7) -0.0054(8) -0.0068(7)
C4 0.0623(8) 0.0749(9) 0.0635(8) 0.0107(7) 0.0066(7) -0.0108(7)
C5 0.0816(10) 0.0794(10) 0.0651(8) 0.0186(7) 0.0145(8) -0.0088(8)
C13 0.0862(12) 0.0906(14) 0.1070(14) 0.0406(11) -0.0104(11) -0.0363(11)
C19 0.0584(9) 0.0658(9) 0.1051(12) 0.0063(9) 0.0067(8) 0.0041(7)
C12 0.0804(11) 0.1008(14) 0.0783(10) 0.0200(9) 0.0123(8) -0.0292(10)
C20 0.0750(10) 0.0751(10) 0.0795(10) 0.0106(8) -0.0020(8) -0.0069(9)
C14 0.1025(14) 0.0542(9) 0.1170(15) 0.0173(10) -0.0230(12) -0.0223(10)
C21 0.0954(12) 0.0808(11) 0.0638(9) -0.0045(8) 0.0124(8) 0.0043(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
C2 C9 1.3548(18) . ?
C2 C1 1.443(2) . ?
C2 C3 1.4904(17) . ?
C3 C4 1.3841(18) . ?
C3 C8 1.3844(18) . ?
C9 C10 1.4837(18) . ?
C9 C16 1.5037(19) . ?
C17 C22 1.3754(18) . ?
C17 C18 1.3839(19) . ?
C17 C16 1.5131(19) . ?
C7 C6 1.368(2) . ?
C7 C8 1.3805(19) . ?
C7 H7 0.9300 . ?
C1 N1 1.1432(18) . ?
C10 C11 1.388(2) . ?
C10 C15 1.392(2) . ?
C18 C19 1.376(2) . ?
C18 H18 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C6 C5 1.368(2) . ?
C6 H6 0.9300 . ?
C22 C21 1.380(2) . ?
C22 H22 0.9300 . ?
C15 C14 1.384(3) . ?
C15 H15 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C13 C12 1.366(3) . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C19 C20 1.360(2) . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C20 C21 1.368(2) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C21 H21 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
C9 C2 C1 119.28(12) . . ?
C9 C2 C3 127.43(12) . . ?
C1 C2 C3 113.23(11) . . ?
C4 C3 C8 117.98(12) . . ?
C4 C3 C2 120.16(12) . . ?
C8 C3 C2 121.82(12) . . ?
C2 C9 C10 121.25(12) . . ?
C2 C9 C16 122.56(12) . . ?
C10 C9 C16 116.16(11) . . ?
C22 C17 C18 117.54(13) . . ?
C22 C17 C16 122.48(12) . . ?
C18 C17 C16 119.90(12) . . ?
C6 C7 C8 120.36(13) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N1 C1 C2 174.96(15) . . ?
C11 C10 C15 117.97(14) . . ?
C11 C10 C9 120.57(12) . . ?
C15 C10 C9 121.45(14) . . ?
C19 C18 C17 120.92(14) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C9 C16 C17 115.96(11) . . ?
C9 C16 H16A 108.3 . . ?
C17 C16 H16A 108.3 . . ?
C9 C16 H16B 108.3 . . ?
C17 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C12 C11 C10 121.35(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C7 C8 C3 120.77(13) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C5 C6 C7 119.65(14) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C17 C22 C21 121.29(14) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C14 C15 C10 120.03(17) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C5 C4 C3 120.89(13) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.29(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C12 C13 C14 119.90(17) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C20 C19 C18 120.81(15) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C13 C12 C11 119.90(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C19 C20 C21 119.21(15) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C13 C14 C15 120.84(17) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C20 C21 C22 120.23(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031