#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/7/7100118.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7100118
_journal_name_full  'Chemical Communications'
_journal_year       2005
loop_
_publ_author_name
'David Vicic'
'Thomas J. Anderson'
'Gavin D. Jones'
'Chris McFarland'
_publ_section_title
;
Analysis of Key Steps in the Catalytic Cross-Coupling
of Alkyl Electrophiles Under Negishi-like Conditions
;
_chemical_formula_sum  'C28 H38 N3 Ni'
_chemical_formula_weight   475.32
_symmetry_cell_setting   monoclinic
_symmetry_space_group_name_H-M  'P 21/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   11.890(10)
_cell_length_b   10.947(17)
_cell_length_c   20.178(19)
_cell_angle_alpha  90.00
_cell_angle_beta   105.977(6)
_cell_angle_gamma  90.00
_cell_volume   2525(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.250
_diffrn_ambient_temperature  173(2)
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
Ni1 Ni 0.42264(3) 0.87648(3) 0.113638(19) 0.02965(13) Uani 1 1 d . . .
N1 N 0.3187(2) 0.9480(2) 0.03413(12) 0.0307(5) Uani 1 1 d . . .
N2 N 0.5020(2) 1.0210(2) 0.11261(12) 0.0276(5) Uani 1 1 d . . .
N3 N 0.5423(2) 0.8522(2) 0.19809(13) 0.0304(5) Uani 1 1 d . . .
C1 C 0.3421(3) 0.7217(3) 0.1127(2) 0.0506(9) Uani 1 1 d . . .
H1A H 0.2932 0.7049 0.0659 0.076 Uiso 1 1 calc R . .
H1B H 0.2928 0.7260 0.1443 0.076 Uiso 1 1 calc R . .
H1C H 0.3998 0.6561 0.1273 0.076 Uiso 1 1 calc R . .
C2 C 0.2112(3) 0.9087(3) -0.00212(17) 0.0400(8) Uani 1 1 d . . .
H2A H 0.1833 0.8339 0.0112 0.048 Uiso 1 1 calc R . .
C3 C 0.1409(3) 0.9706(3) -0.05662(17) 0.0425(8) Uani 1 1 d . . .
H3A H 0.0651 0.9398 -0.0785 0.051 Uiso 1 1 calc R . .
C4 C 0.1785(2) 1.0789(3) -0.08102(15) 0.0306(6) Uani 1 1 d . . .
C5 C 0.2881(2) 1.1203(3) -0.04481(14) 0.0275(6) Uani 1 1 d . . .
H5A H 0.3185 1.1924 -0.0597 0.033 Uiso 1 1 calc R . .
C6 C 0.3555(2) 1.0580(2) 0.01343(14) 0.0262(6) Uani 1 1 d . . .
C7 C 0.0969(3) 1.1456(3) -0.14197(15) 0.0337(7) Uani 1 1 d . . .
C8 C 0.0542(3) 1.0555(4) -0.20212(16) 0.0452(8) Uani 1 1 d . . .
H8A H 0.1217 1.0181 -0.2132 0.068 Uiso 1 1 calc R . .
H8B H 0.0069 1.0993 -0.2426 0.068 Uiso 1 1 calc R . .
H8C H 0.0067 0.9917 -0.1890 0.068 Uiso 1 1 calc R . .
C9 C -0.0107(3) 1.1919(4) -0.12066(18) 0.0486(9) Uani 1 1 d . . .
H9A H 0.0146 1.2503 -0.0827 0.073 Uiso 1 1 calc R . .
H9B H -0.0499 1.1226 -0.1057 0.073 Uiso 1 1 calc R . .
H9C H -0.0650 1.2321 -0.1601 0.073 Uiso 1 1 calc R . .
C10 C 0.1562(3) 1.2533(3) -0.16589(17) 0.0435(8) Uani 1 1 d . . .
H10A H 0.2261 1.2249 -0.1781 0.065 Uiso 1 1 calc R . .
H10B H 0.1787 1.3136 -0.1287 0.065 Uiso 1 1 calc R . .
H10C H 0.1019 1.2908 -0.2063 0.065 Uiso 1 1 calc R . .
C11 C 0.4628(2) 1.1024(2) 0.06057(14) 0.0260(6) Uani 1 1 d . . .
C12 C 0.5176(2) 1.2150(2) 0.06223(14) 0.0267(6) Uani 1 1 d . . .
H12A H 0.4914 1.2703 0.0249 0.032 Uiso 1 1 calc R . .
C13 C 0.6107(2) 1.2471(3) 0.11833(14) 0.0278(6) Uani 1 1 d . . .
C14 C 0.6494(2) 1.1598(3) 0.17130(15) 0.0288(6) Uani 1 1 d . . .
H14A H 0.7137 1.1780 0.2099 0.035 Uiso 1 1 calc R . .
C15 C 0.5941(2) 1.0483(3) 0.16716(15) 0.0278(6) Uani 1 1 d . . .
C16 C 0.6681(3) 1.3736(3) 0.12687(15) 0.0309(6) Uani 1 1 d . . .
C17 C 0.6652(5) 1.4291(4) 0.1953(2) 0.0746(14) Uani 1 1 d . . .
H17A H 0.5839 1.4354 0.1972 0.112 Uiso 1 1 calc R . .
H17B H 0.7005 1.5106 0.1999 0.112 Uiso 1 1 calc R . .
H17C H 0.7093 1.3770 0.2331 0.112 Uiso 1 1 calc R . .
C18 C 0.7966(3) 1.3608(4) 0.1265(3) 0.0687(13) Uani 1 1 d . . .
H18A H 0.8353 1.4404 0.1357 0.103 Uiso 1 1 calc R . .
H18B H 0.8002 1.3312 0.0813 0.103 Uiso 1 1 calc R . .
H18C H 0.8362 1.3025 0.1621 0.103 Uiso 1 1 calc R . .
C19 C 0.6095(4) 1.4591(4) 0.0695(2) 0.0728(14) Uani 1 1 d . . .
H19A H 0.5276 1.4704 0.0691 0.109 Uiso 1 1 calc R . .
H19B H 0.6131 1.4245 0.0253 0.109 Uiso 1 1 calc R . .
H19C H 0.6497 1.5382 0.0766 0.109 Uiso 1 1 calc R . .
C20 C 0.6173(2) 0.9498(3) 0.21752(15) 0.0294(6) Uani 1 1 d . . .
C21 C 0.7057(2) 0.9515(3) 0.27957(15) 0.0306(6) Uani 1 1 d . . .
H21A H 0.7541 1.0217 0.2914 0.037 Uiso 1 1 calc R . .
C22 C 0.7241(3) 0.8529(3) 0.32417(15) 0.0333(7) Uani 1 1 d . . .
C23 C 0.6476(3) 0.7543(3) 0.30347(17) 0.0381(7) Uani 1 1 d . . .
H23A H 0.6562 0.6840 0.3321 0.046 Uiso 1 1 calc R . .
C24 C 0.5602(3) 0.7573(3) 0.24247(16) 0.0357(7) Uani 1 1 d . . .
H24A H 0.5096 0.6887 0.2309 0.043 Uiso 1 1 calc R . .
C25 C 0.8204(3) 0.8535(3) 0.39244(16) 0.0378(7) Uani 1 1 d . . .
C26 C 0.7635(3) 0.8805(3) 0.45025(17) 0.0418(8) Uani 1 1 d . . .
H26A H 0.7048 0.8178 0.4505 0.063 Uiso 1 1 calc R . .
H26B H 0.7257 0.9608 0.4426 0.063 Uiso 1 1 calc R . .
H26C H 0.8235 0.8802 0.4947 0.063 Uiso 1 1 calc R . .
C27 C 0.9117(3) 0.9529(5) 0.39480(19) 0.0617(12) Uani 1 1 d . . .
H27A H 0.9724 0.9486 0.4388 0.093 Uiso 1 1 calc R . .
H27B H 0.8739 1.0333 0.3902 0.093 Uiso 1 1 calc R . .
H27C H 0.9472 0.9407 0.3569 0.093 Uiso 1 1 calc R . .
C28 C 0.8803(4) 0.7299(4) 0.4047(2) 0.0741(15) Uani 1 1 d . . .
H28A H 0.8232 0.6670 0.4075 0.111 Uiso 1 1 calc R . .
H28B H 0.9430 0.7318 0.4480 0.111 Uiso 1 1 calc R . .
H28C H 0.9136 0.7110 0.3665 0.111 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
Ni1 0.0281(2) 0.01898(19) 0.0398(2) -0.00138(15) 0.00578(16) -0.00187(15)
N1 0.0284(13) 0.0250(12) 0.0368(14) -0.0045(10) 0.0055(10) -0.0051(10)
N2 0.0232(12) 0.0232(12) 0.0343(13) -0.0014(9) 0.0045(10) -0.0005(9)
N3 0.0294(13) 0.0227(12) 0.0392(14) 0.0005(10) 0.0092(10) 0.0031(10)
C1 0.052(2) 0.0304(17) 0.060(2) 0.0050(15) -0.0015(17) -0.0038(15)
C2 0.0352(17) 0.0299(16) 0.050(2) -0.0008(13) 0.0031(14) -0.0119(13)
C3 0.0316(17) 0.0413(19) 0.0464(19) -0.0063(14) -0.0031(14) -0.0156(14)
C4 0.0263(14) 0.0340(15) 0.0289(15) -0.0079(12) 0.0035(11) -0.0023(12)
C5 0.0249(13) 0.0295(14) 0.0282(15) -0.0050(11) 0.0077(11) -0.0026(11)
C6 0.0212(13) 0.0247(13) 0.0320(15) -0.0061(11) 0.0063(11) -0.0043(10)
C7 0.0273(15) 0.0413(18) 0.0299(16) -0.0079(12) 0.0037(12) -0.0012(12)
C8 0.0403(19) 0.061(2) 0.0311(17) -0.0114(15) 0.0040(14) -0.0111(17)
C9 0.0345(18) 0.063(2) 0.046(2) -0.0031(17) 0.0065(15) 0.0131(17)
C10 0.0420(19) 0.0443(19) 0.0361(18) 0.0041(14) -0.0026(14) -0.0027(15)
C11 0.0194(12) 0.0250(14) 0.0329(15) -0.0025(11) 0.0061(11) 0.0006(10)
C12 0.0231(13) 0.0250(13) 0.0305(15) 0.0026(11) 0.0048(11) -0.0017(11)
C13 0.0205(13) 0.0264(14) 0.0352(15) 0.0020(11) 0.0056(11) -0.0022(11)
C14 0.0193(13) 0.0269(14) 0.0353(16) -0.0010(11) -0.0010(11) -0.0023(10)
C15 0.0206(13) 0.0240(14) 0.0363(16) 0.0012(11) 0.0034(11) 0.0034(10)
C16 0.0270(14) 0.0261(14) 0.0369(16) 0.0026(12) 0.0041(12) -0.0064(12)
C17 0.120(4) 0.039(2) 0.073(3) -0.011(2) 0.039(3) -0.026(3)
C18 0.040(2) 0.058(3) 0.105(4) -0.004(2) 0.016(2) -0.0172(19)
C19 0.068(3) 0.049(2) 0.083(3) 0.023(2) -0.011(2) -0.028(2)
C20 0.0247(14) 0.0229(13) 0.0399(17) -0.0004(11) 0.0079(12) 0.0025(11)
C21 0.0266(14) 0.0271(14) 0.0370(16) 0.0018(11) 0.0069(12) 0.0078(11)
C22 0.0316(15) 0.0356(17) 0.0355(16) 0.0062(12) 0.0139(13) 0.0110(12)
C23 0.0389(17) 0.0339(16) 0.0446(18) 0.0119(13) 0.0165(14) 0.0103(13)
C24 0.0395(17) 0.0226(14) 0.0477(18) 0.0069(12) 0.0168(14) 0.0027(12)
C25 0.0330(16) 0.0466(19) 0.0337(17) 0.0111(13) 0.0092(13) 0.0168(14)
C26 0.0468(19) 0.0428(19) 0.0379(18) 0.0079(14) 0.0154(15) 0.0086(15)
C27 0.0322(19) 0.107(4) 0.040(2) 0.020(2) 0.0000(15) -0.009(2)
C28 0.079(3) 0.078(3) 0.052(2) -0.001(2) -0.005(2) 0.056(3)
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
Ni1 N2 1.845(3) . ?
Ni1 N1 1.903(3) . ?
Ni1 N3 1.914(3) . ?
Ni1 C1 1.944(4) . ?
N1 C2 1.356(4) . ?
N1 C6 1.385(4) . ?
N2 C15 1.355(4) . ?
N2 C11 1.358(4) . ?
N3 C24 1.350(4) . ?
N3 C20 1.377(4) . ?
C2 C3 1.364(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.384(4) . ?
C4 C7 1.526(4) . ?
C5 C6 1.403(4) . ?
C6 C11 1.450(4) . ?
C7 C10 1.518(5) . ?
C7 C8 1.537(4) . ?
C7 C9 1.544(5) . ?
C11 C12 1.390(4) . ?
C12 C13 1.393(4) . ?
C13 C14 1.413(4) . ?
C13 C16 1.533(4) . ?
C14 C15 1.378(4) . ?
C15 C20 1.455(4) . ?
C16 C19 1.503(5) . ?
C16 C17 1.518(5) . ?
C16 C18 1.536(5) . ?
C20 C21 1.396(4) . ?
C21 C22 1.384(4) . ?
C22 C23 1.399(5) . ?
C22 C25 1.530(4) . ?
C23 C24 1.375(5) . ?
C25 C28 1.518(5) . ?
C25 C27 1.529(5) . ?
C25 C26 1.530(4) . ?