#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/7/7100117.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_7100117 _journal_name_full 'Chemical Communications' _journal_year 2005 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' 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 'C37 H50 Cl4 I N3 Ni' _chemical_formula_weight 864.21 _symmetry_cell_setting Monoclinic 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 12.78(2) _cell_length_b 17.04(2) _cell_length_c 19.13(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.82(2) _cell_angle_gamma 90.00 _cell_volume 4028(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.425 _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 I1 I 0.23491(5) 0.22706(3) 0.33998(3) 0.0410(2) Uani 1 1 d . . . Ni2 Ni 0.09477(8) -0.04555(6) 0.56222(6) 0.0310(3) Uani 1 1 d . . . Cl1 Cl 0.4350(3) 0.6717(4) 0.0346(2) 0.1060(15) Uani 1 1 d . . . Cl2 Cl 0.3514(5) 0.6731(9) 0.1560(4) 0.247(6) Uani 1 1 d . . . Cl3 Cl 0.3789(5) 0.4740(5) 0.2843(4) 0.168(3) Uani 1 1 d . . . Cl4 Cl 0.5408(11) 0.4409(7) 0.4179(6) 0.235(5) Uani 1 1 d . . . N1 N 0.0503(6) -0.0154(4) 0.6471(4) 0.0324(14) Uani 1 1 d . . . N2 N 0.1690(5) 0.0506(4) 0.5797(3) 0.0280(13) Uani 1 1 d . . . N3 N 0.1651(6) -0.0505(4) 0.4844(4) 0.0371(16) Uani 1 1 d . . . C1 C 0.0291(8) -0.1476(5) 0.5466(5) 0.042(2) Uani 1 1 d . . . H1A H 0.0044 -0.1578 0.4945 0.063 Uiso 1 1 calc R . . H1B H -0.0327 -0.1496 0.5680 0.063 Uiso 1 1 calc R . . H1C H 0.0823 -0.1875 0.5692 0.063 Uiso 1 1 calc R . . C2 C 0.1629(7) -0.1089(5) 0.4374(5) 0.0383(19) Uani 1 1 d . . . H2A H 0.1176 -0.1528 0.4387 0.046 Uiso 1 1 calc R . . C3 C 0.2227(7) -0.1086(5) 0.3873(5) 0.0393(19) Uani 1 1 d . . . H3A H 0.2167 -0.1513 0.3545 0.047 Uiso 1 1 calc R . . C4 C 0.2917(7) -0.0469(5) 0.3838(5) 0.0354(18) Uani 1 1 d . . . C5 C 0.2907(7) 0.0167(5) 0.4313(5) 0.0354(18) Uani 1 1 d . . . H5A H 0.3338 0.0618 0.4299 0.042 Uiso 1 1 calc R . . C6 C 0.2279(7) 0.0133(5) 0.4792(4) 0.0324(17) Uani 1 1 d . . . C7 C 0.2260(6) 0.0754(4) 0.5335(4) 0.0295(16) Uani 1 1 d . . . C8 C 0.2753(6) 0.1475(5) 0.5423(4) 0.0299(16) Uani 1 1 d . . . H8A H 0.3149 0.1647 0.5093 0.036 Uiso 1 1 calc R . . C9 C 0.2672(7) 0.1956(5) 0.6001(4) 0.0323(17) Uani 1 1 d . . . C10 C 0.2091(7) 0.1673(5) 0.6479(4) 0.0337(17) Uani 1 1 d . . . H10A H 0.2039 0.1976 0.6885 0.040 Uiso 1 1 calc R . . C11 C 0.1594(7) 0.0945(5) 0.6351(5) 0.0347(18) Uani 1 1 d . . . C12 C 0.0944(7) 0.0547(5) 0.6774(5) 0.0332(17) Uani 1 1 d . . . C13 C 0.0812(7) 0.0794(5) 0.7428(5) 0.0362(18) Uani 1 1 d . . . H13A H 0.1161 0.1263 0.7633 0.043 Uiso 1 1 calc R . . C14 C 0.0181(7) 0.0379(5) 0.7806(5) 0.0366(18) Uani 1 1 d . . . C15 C -0.0305(7) -0.0313(5) 0.7467(5) 0.040(2) Uani 1 1 d . . . H15A H -0.0749 -0.0621 0.7690 0.048 Uiso 1 1 calc R . . C16 C -0.0139(7) -0.0543(5) 0.6813(5) 0.0366(18) Uani 1 1 d . . . H16A H -0.0497 -0.1002 0.6590 0.044 Uiso 1 1 calc R . . C17 C 0.0106(9) 0.0621(5) 0.8555(5) 0.045(2) Uani 1 1 d . . . C18 C -0.0617(10) 0.0079(6) 0.8860(6) 0.058(3) Uani 1 1 d . . . H18A H -0.1351 0.0085 0.8541 0.087 Uiso 1 1 calc R . . H18B H -0.0636 0.0260 0.9343 0.087 Uiso 1 1 calc R . . H18C H -0.0329 -0.0457 0.8892 0.087 Uiso 1 1 calc R . . C19 C 0.1273(9) 0.0557(7) 0.9066(5) 0.055(3) Uani 1 1 d . . . H19A H 0.1554 0.0026 0.9037 0.083 Uiso 1 1 calc R . . H19B H 0.1249 0.0666 0.9565 0.083 Uiso 1 1 calc R . . H19C H 0.1747 0.0939 0.8917 0.083 Uiso 1 1 calc R . . C20 C -0.0303(10) 0.1466(6) 0.8529(6) 0.054(3) Uani 1 1 d . . . H20A H -0.0996 0.1509 0.8164 0.081 Uiso 1 1 calc R . . H20B H 0.0226 0.1818 0.8402 0.081 Uiso 1 1 calc R . . H20C H -0.0402 0.1612 0.9003 0.081 Uiso 1 1 calc R . . C21 C 0.3181(8) 0.2781(5) 0.6110(4) 0.0344(18) Uani 1 1 d . . . C22 C 0.3702(8) -0.0462(5) 0.3361(5) 0.040(2) Uani 1 1 d . . . C23 C 0.4856(10) -0.0489(11) 0.3822(7) 0.083(5) Uani 1 1 d . . . H23A H 0.5000 -0.0024 0.4134 0.124 Uiso 1 1 calc R . . H23B H 0.5354 -0.0497 0.3508 0.124 Uiso 1 1 calc R . . H23C H 0.4961 -0.0963 0.4121 0.124 Uiso 1 1 calc R . . C24 C 0.3543(14) -0.1171(8) 0.2847(10) 0.091(5) Uani 1 1 d . . . H24A H 0.2825 -0.1143 0.2508 0.137 Uiso 1 1 calc R . . H24B H 0.3604 -0.1657 0.3128 0.137 Uiso 1 1 calc R . . H24C H 0.4099 -0.1164 0.2576 0.137 Uiso 1 1 calc R . . C25 C 0.3538(11) 0.0270(7) 0.2875(6) 0.064(3) Uani 1 1 d . . . H25A H 0.2798 0.0274 0.2565 0.097 Uiso 1 1 calc R . . H25B H 0.4053 0.0261 0.2574 0.097 Uiso 1 1 calc R . . H25C H 0.3658 0.0742 0.3178 0.097 Uiso 1 1 calc R . . C26 C 0.2288(8) 0.3387(6) 0.6128(6) 0.048(2) Uani 1 1 d . . . H26A H 0.1700 0.3340 0.5686 0.072 Uiso 1 1 calc R . . H26B H 0.2593 0.3918 0.6160 0.072 Uiso 1 1 calc R . . H26C H 0.2006 0.3288 0.6550 0.072 Uiso 1 1 calc R . . C27 C 0.4025(8) 0.2784(6) 0.6849(6) 0.046(2) Uani 1 1 d . . . H27A H 0.4598 0.2405 0.6841 0.070 Uiso 1 1 calc R . . H27B H 0.3673 0.2640 0.7230 0.070 Uiso 1 1 calc R . . H27C H 0.4340 0.3310 0.6946 0.070 Uiso 1 1 calc R . . C28 C 0.3699(10) 0.3011(6) 0.5515(6) 0.054(3) Uani 1 1 d . . . H28A H 0.3160 0.2985 0.5048 0.081 Uiso 1 1 calc R . . H28B H 0.4295 0.2650 0.5512 0.081 Uiso 1 1 calc R . . H28C H 0.3980 0.3548 0.5598 0.081 Uiso 1 1 calc R . . C29 C 0.8291(17) 0.1944(9) 0.2202(10) 0.091(5) Uani 1 1 d . . . H29A H 0.8320 0.2029 0.2698 0.109 Uiso 1 1 calc R . . C30 C 0.7355(16) 0.1706(9) 0.1751(9) 0.085(4) Uani 1 1 d . . . H30A H 0.6751 0.1593 0.1937 0.102 Uiso 1 1 calc R . . C31 C 0.7270(12) 0.1627(7) 0.1052(9) 0.074(4) Uani 1 1 d . . . H31A H 0.6587 0.1490 0.0742 0.088 Uiso 1 1 calc R . . C32 C 0.8147(13) 0.1739(7) 0.0750(8) 0.074(4) Uani 1 1 d . . . C33 C 0.9140(12) 0.1968(7) 0.1244(10) 0.082(5) Uani 1 1 d . . . H33A H 0.9767 0.2052 0.1074 0.098 Uiso 1 1 calc R . . C34 C 0.9190(15) 0.2067(8) 0.1968(9) 0.084(5) Uani 1 1 d . . . H34A H 0.9848 0.2221 0.2298 0.101 Uiso 1 1 calc R . . C35 C 0.4486(13) 0.7088(11) 0.1213(9) 0.092(5) Uani 1 1 d . . . H35A H 0.5202 0.6942 0.1527 0.111 Uiso 1 1 calc R . . H35B H 0.4439 0.7668 0.1194 0.111 Uiso 1 1 calc R . . C37 C 0.417(2) 0.4419(15) 0.390(2) 0.194(17) Uani 1 1 d . . . H37A H 0.3858 0.4797 0.4184 0.233 Uiso 1 1 calc R . . H37B H 0.3874 0.3892 0.3952 0.233 Uiso 1 1 calc R . . C40 C 0.8007(19) 0.1619(12) -0.0029(11) 0.124(7) Uani 1 1 d . . . H40A H 0.7241 0.1529 -0.0263 0.186 Uiso 1 1 calc R . . H40B H 0.8430 0.1162 -0.0106 0.186 Uiso 1 1 calc R . . H40C H 0.8258 0.2086 -0.0238 0.186 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 I1 0.0475(4) 0.0410(3) 0.0362(3) 0.0070(2) 0.0137(2) 0.0081(3) Ni2 0.0317(5) 0.0300(5) 0.0300(5) -0.0014(4) 0.0055(4) -0.0034(4) Cl1 0.083(3) 0.175(5) 0.057(2) -0.017(2) 0.0125(18) -0.016(3) Cl2 0.092(4) 0.57(2) 0.094(4) -0.018(7) 0.046(3) -0.022(7) Cl3 0.097(4) 0.230(8) 0.179(7) -0.065(6) 0.042(4) -0.035(4) Cl4 0.230(11) 0.240(11) 0.210(10) 0.023(8) 0.011(8) 0.016(9) N1 0.033(3) 0.034(3) 0.030(3) 0.002(3) 0.006(3) -0.006(3) N2 0.027(3) 0.030(3) 0.026(3) 0.001(3) 0.005(3) -0.003(3) N3 0.039(4) 0.035(4) 0.031(4) 0.001(3) -0.002(3) 0.001(3) C1 0.040(5) 0.040(5) 0.044(5) -0.011(4) 0.008(4) -0.010(4) C2 0.038(5) 0.035(4) 0.039(5) -0.011(4) 0.006(4) -0.002(4) C3 0.042(5) 0.032(4) 0.043(5) -0.008(4) 0.010(4) 0.000(4) C4 0.036(4) 0.036(4) 0.032(4) -0.001(3) 0.006(3) 0.007(4) C5 0.040(4) 0.024(4) 0.038(4) -0.001(3) 0.001(4) 0.000(3) C6 0.031(4) 0.037(4) 0.029(4) -0.004(3) 0.007(3) 0.000(3) C7 0.033(4) 0.028(4) 0.026(4) 0.000(3) 0.005(3) 0.000(3) C8 0.028(4) 0.038(4) 0.021(3) 0.000(3) 0.002(3) -0.002(3) C9 0.039(4) 0.028(4) 0.028(4) 0.003(3) 0.005(3) 0.003(3) C10 0.038(4) 0.032(4) 0.030(4) -0.001(3) 0.007(3) -0.005(3) C11 0.035(4) 0.031(4) 0.036(4) -0.003(3) 0.005(3) 0.005(3) C12 0.032(4) 0.027(4) 0.037(4) 0.006(3) 0.004(3) -0.002(3) C13 0.038(4) 0.034(4) 0.036(4) 0.001(3) 0.007(4) -0.008(4) C14 0.041(5) 0.037(4) 0.034(4) 0.001(3) 0.012(4) -0.005(4) C15 0.040(5) 0.035(4) 0.048(5) -0.001(4) 0.020(4) -0.008(4) C16 0.036(4) 0.034(4) 0.040(5) -0.005(3) 0.009(4) -0.007(3) C17 0.073(7) 0.040(5) 0.028(4) 0.000(4) 0.023(4) -0.019(5) C18 0.084(8) 0.052(6) 0.047(6) 0.003(5) 0.033(6) -0.030(6) C19 0.067(7) 0.064(7) 0.033(5) -0.004(5) 0.008(5) -0.016(5) C20 0.074(7) 0.053(6) 0.048(6) 0.000(5) 0.039(5) -0.001(5) C21 0.051(5) 0.025(4) 0.029(4) -0.005(3) 0.012(4) -0.001(3) C22 0.044(5) 0.043(5) 0.039(5) 0.000(4) 0.021(4) 0.012(4) C23 0.051(7) 0.144(14) 0.062(8) 0.013(8) 0.029(6) 0.010(8) C24 0.115(12) 0.059(8) 0.125(13) -0.040(8) 0.078(11) -0.004(8) C25 0.084(8) 0.068(7) 0.051(6) 0.022(6) 0.034(6) 0.025(6) C26 0.043(5) 0.040(5) 0.063(6) 0.005(4) 0.016(5) 0.009(4) C27 0.045(5) 0.037(5) 0.054(6) -0.004(4) 0.008(4) -0.012(4) C28 0.080(8) 0.044(5) 0.045(6) -0.010(4) 0.029(5) -0.022(5) C29 0.117(14) 0.061(8) 0.094(12) 0.019(8) 0.026(11) 0.020(9) C30 0.108(13) 0.072(9) 0.082(11) 0.005(8) 0.035(10) 0.016(9) C31 0.073(9) 0.056(7) 0.097(11) 0.002(7) 0.031(8) 0.000(6) C32 0.101(11) 0.048(6) 0.083(9) 0.011(6) 0.043(8) 0.024(7) C33 0.067(9) 0.043(6) 0.140(15) 0.015(8) 0.035(9) 0.016(6) C34 0.103(12) 0.057(7) 0.072(10) 0.003(7) -0.018(9) 0.018(8) C35 0.069(9) 0.116(13) 0.087(11) -0.016(9) 0.011(8) -0.007(9) C37 0.16(2) 0.15(2) 0.35(4) 0.14(2) 0.19(3) 0.073(17) C40 0.17(2) 0.108(14) 0.125(17) 0.018(12) 0.090(15) 0.030(14) 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 Ni2 N2 1.880(7) . ? Ni2 C1 1.921(9) . ? Ni2 N1 1.923(8) . ? Ni2 N3 1.927(9) . ? Cl1 C35 1.741(17) . ? Cl2 C35 1.665(19) . ? Cl3 C37 2.03(3) . ? Cl4 C37 1.53(3) . ? N1 C16 1.346(11) . ? N1 C12 1.384(10) . ? N2 C11 1.328(11) . ? N2 C7 1.349(10) . ? N3 C2 1.336(11) . ? N3 C6 1.370(11) . ? C2 C3 1.370(13) . ? C3 C4 1.385(13) . ? C4 C5 1.416(12) . ? C4 C22 1.520(13) . ? C5 C6 1.364(13) . ? C6 C7 1.489(11) . ? C7 C8 1.371(11) . ? C8 C9 1.402(12) . ? C9 C10 1.401(12) . ? C9 C21 1.542(11) . ? C10 C11 1.387(12) . ? C11 C12 1.465(12) . ? C12 C13 1.370(13) . ? C13 C14 1.405(12) . ? C14 C15 1.410(12) . ? C14 C17 1.516(13) . ? C15 C16 1.379(13) . ? C17 C18 1.525(13) . ? C17 C20 1.529(15) . ? C17 C19 1.565(16) . ? C21 C28 1.508(13) . ? C21 C27 1.544(13) . ? C21 C26 1.546(13) . ? C22 C23 1.514(16) . ? C22 C25 1.537(14) . ? C22 C24 1.537(15) . ? C29 C30 1.35(2) . ? C29 C34 1.35(2) . ? C30 C31 1.32(2) . ? C31 C32 1.40(2) . ? C32 C33 1.43(2) . ? C32 C40 1.47(2) . ? C33 C34 1.38(2) . ? _cod_database_code 7100117