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#$Date: 2016-03-21 18:35:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178817 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/71/4107115.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_4107115
loop_
_publ_author_name
'Masato Ohashi'
'Ippei Takeda'
'Masashi Ikawa'
'Sensuke Ogoshi'
_publ_contact_author_address
;
 Department of Applied Chemistry,
 Faculty of Engineering, Suita, Osaka 565-0871, Japan
 Center for Atomic and Molecular Technologies, Osaka University, 
 Suita, Osaka 565-0871, Japan
;
_publ_contact_author_email       ohashi@chem.eng.osaka-u.ac.jp
_publ_contact_author_fax         '+81 6 6879 7394'
_publ_contact_author_name        'Assit. Prof. Masato Ohashi'
_publ_contact_author_phone       '+81 6 6879 7393'
_publ_section_title
;
 Nickel-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of 1,3-Dienes with
 Nitriles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18018
_journal_page_last               18021
_journal_paper_doi               10.1021/ja208162w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C45 H61 N Ni P'
_chemical_formula_weight         705.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.318(2)
_cell_angle_beta                 97.314(2)
_cell_angle_gamma                108.600(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8805(6)
_cell_length_b                   12.7636(8)
_cell_length_c                   16.4167(8)
_cell_measurement_temperature    123(2)
_cell_volume                     1921.07(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.1106
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15141
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_correction_T_min  0.8456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             762
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.451
_refine_diff_density_min         -2.055
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0294P)²+12.6272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.2242
_reflns_number_gt                4066
_reflns_number_total             6727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja208162w_si_002_3.cif
_cod_data_source_block           23c
_cod_original_cell_volume        1921.06(19)
_cod_database_code               4107115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Ni1 Ni 0.00167(10) 0.31043(7) 0.21007(5) 0.0277(3) Uani 1 1 d .
P1 P 0.1514(2) 0.47548(15) 0.27270(11) 0.0281(4) Uani 1 1 d .
N1 N 0.0718(6) 0.2948(5) 0.1118(3) 0.0339(14) Uani 1 1 d .
H1 H 0.1418 0.3508 0.1002 0.041 Uiso 1 1 calc R
C1 C -0.1319(8) 0.2687(6) 0.2917(4) 0.0359(18) Uani 1 1 d .
H1A H -0.0973 0.2385 0.3401 0.043 Uiso 1 1 calc R
H1B H -0.1865 0.3194 0.3052 0.043 Uiso 1 1 calc R
C2 C -0.1843(8) 0.1935(6) 0.2138(4) 0.0325(16) Uani 1 1 d .
C3 C -0.0914(8) 0.1413(6) 0.1816(4) 0.0350(17) Uani 1 1 d .
C4 C -0.1032(8) 0.1101(6) 0.0885(4) 0.0310(16) Uani 1 1 d .
H4A H -0.0939 0.0353 0.0759 0.037 Uiso 1 1 calc R
H4B H -0.1994 0.1066 0.0598 0.037 Uiso 1 1 calc R
C5 C 0.0149(7) 0.1962(6) 0.0572(4) 0.0273(15) Uani 1 1 d .
C6 C -0.3226(7) 0.1892(6) 0.1602(4) 0.0276(15) Uani 1 1 d .
C7 C 0.0061(8) 0.1002(6) 0.2368(4) 0.0289(16) Uani 1 1 d .
C8 C 0.0434(7) 0.1719(6) -0.0212(4) 0.0285(15) Uani 1 1 d .
H8 H -0.0074 0.0969 -0.0476 0.034 Uiso 1 1 calc R
C9 C 0.1360(7) 0.2391(5) -0.0709(4) 0.0254(15) Uani 1 1 d .
C10 C 0.1203(8) 0.1997(6) -0.1559(4) 0.0346(17) Uani 1 1 d .
H10 H 0.0503 0.1283 -0.1782 0.042 Uiso 1 1 calc R
C11 C 0.2006(9) 0.2587(6) -0.2087(5) 0.0391(18) Uani 1 1 d .
H11 H 0.1852 0.2280 -0.2658 0.047 Uiso 1 1 calc R
C12 C 0.3040(9) 0.3632(6) -0.1787(5) 0.0406(19) Uani 1 1 d .
H12 H 0.3588 0.4053 -0.2150 0.049 Uiso 1 1 calc R
C13 C 0.3254(9) 0.4043(7) -0.0957(5) 0.0425(19) Uani 1 1 d .
H13 H 0.3966 0.4755 -0.0744 0.051 Uiso 1 1 calc R
C14 C 0.2463(8) 0.3450(6) -0.0423(5) 0.0366(18) Uani 1 1 d .
H14 H 0.2659 0.3755 0.0151 0.044 Uiso 1 1 calc R
C15 C -0.0382(8) 0.0559(6) 0.3073(4) 0.0352(17) Uani 1 1 d .
H15 H -0.1270 0.0581 0.3225 0.042 Uiso 1 1 calc R
C16 C 0.0453(9) 0.0090(6) 0.3552(5) 0.0423(19) Uani 1 1 d .
H16 H 0.0149 -0.0185 0.4037 0.051 Uiso 1 1 calc R
C17 C 0.1725(9) 0.0019(6) 0.3329(5) 0.0409(19) Uani 1 1 d .
H17 H 0.2299 -0.0302 0.3659 0.049 Uiso 1 1 calc R
C18 C 0.2159(8) 0.0418(6) 0.2621(5) 0.0366(18) Uani 1 1 d .
H18 H 0.3020 0.0353 0.2457 0.044 Uiso 1 1 calc R
C19 C 0.1349(7) 0.0910(5) 0.2153(4) 0.0289(16) Uani 1 1 d .
H19 H 0.1671 0.1192 0.1674 0.035 Uiso 1 1 calc R
C20 C -0.4353(8) 0.0886(6) 0.1429(5) 0.0380(18) Uani 1 1 d .
H20 H -0.4239 0.0256 0.1651 0.046 Uiso 1 1 calc R
C21 C -0.5655(8) 0.0781(7) 0.0935(5) 0.0393(18) Uani 1 1 d .
H21 H -0.6429 0.0085 0.0828 0.047 Uiso 1 1 calc R
C22 C -0.5823(8) 0.1677(7) 0.0604(5) 0.0407(19) Uani 1 1 d .
H22 H -0.6713 0.1609 0.0268 0.049 Uiso 1 1 calc R
C23 C -0.4690(9) 0.2679(7) 0.0761(5) 0.047(2) Uani 1 1 d .
H23 H -0.4796 0.3300 0.0523 0.056 Uiso 1 1 calc R
C24 C -0.3411(7) 0.2789(6) 0.1258(5) 0.0378(18) Uani 1 1 d .
H24 H -0.2645 0.3489 0.1367 0.045 Uiso 1 1 calc R
C25 C 0.3176(8) 0.4533(6) 0.3240(4) 0.0342(17) Uani 1 1 d .
H25 H 0.3855 0.5271 0.3548 0.041 Uiso 1 1 calc R
C26 C 0.2782(8) 0.3733(7) 0.3872(5) 0.0383(18) Uani 1 1 d .
H26A H 0.2054 0.3014 0.3585 0.046 Uiso 1 1 calc R
H26B H 0.2343 0.4060 0.4298 0.046 Uiso 1 1 calc R
C27 C 0.4120(9) 0.3514(7) 0.4300(5) 0.046(2) Uani 1 1 d .
H27A H 0.4784 0.4214 0.4654 0.056 Uiso 1 1 calc R
H27B H 0.3811 0.2947 0.4666 0.056 Uiso 1 1 calc R
C28 C 0.4927(9) 0.3105(7) 0.3675(5) 0.044(2) Uani 1 1 d .
H28A H 0.5821 0.3034 0.3973 0.053 Uiso 1 1 calc R
H28B H 0.4310 0.2356 0.3370 0.053 Uiso 1 1 calc R
C29 C 0.5319(9) 0.3915(7) 0.3060(5) 0.048(2) Uani 1 1 d .
H29A H 0.5800 0.3616 0.2643 0.057 Uiso 1 1 calc R
H29B H 0.6009 0.4644 0.3358 0.057 Uiso 1 1 calc R
C30 C 0.3950(8) 0.4091(7) 0.2611(4) 0.0387(19) Uani 1 1 d .
H30A H 0.4232 0.4630 0.2221 0.046 Uiso 1 1 calc R
H30B H 0.3285 0.3371 0.2284 0.046 Uiso 1 1 calc R
C31 C 0.0900(7) 0.5462(6) 0.3576(4) 0.0269(15) Uani 1 1 d .
H31 H 0.0485 0.4867 0.3913 0.032 Uiso 1 1 calc R
C32 C 0.2067(8) 0.6413(6) 0.4202(4) 0.0354(17) Uani 1 1 d .
H32A H 0.2846 0.6139 0.4428 0.042 Uiso 1 1 calc R
H32B H 0.2502 0.7045 0.3911 0.042 Uiso 1 1 calc R
C33 C 0.1416(8) 0.6822(6) 0.4918(4) 0.0314(16) Uani 1 1 d .
H33A H 0.2173 0.7459 0.5290 0.038 Uiso 1 1 calc R
H33B H 0.1076 0.6212 0.5246 0.038 Uiso 1 1 calc R
C34 C 0.0139(8) 0.7193(6) 0.4592(4) 0.0366(18) Uani 1 1 d .
H34A H -0.0295 0.7413 0.5066 0.044 Uiso 1 1 calc R
H34B H 0.0497 0.7855 0.4315 0.044 Uiso 1 1 calc R
C35 C -0.1024(8) 0.6246(6) 0.3974(4) 0.0350(17) Uani 1 1 d .
H35A H -0.1454 0.5613 0.4265 0.042 Uiso 1 1 calc R
H35B H -0.1807 0.6518 0.3749 0.042 Uiso 1 1 calc R
C36 C -0.0364(8) 0.5846(6) 0.3258(4) 0.0308(16) Uani 1 1 d .
H36A H -0.0013 0.6464 0.2938 0.037 Uiso 1 1 calc R
H36B H -0.1121 0.5217 0.2878 0.037 Uiso 1 1 calc R
C37 C 0.2159(8) 0.5705(6) 0.1985(4) 0.0284(15) Uani 1 1 d .
H37 H 0.2703 0.5336 0.1646 0.034 Uiso 1 1 calc R
C38 C 0.0907(8) 0.5790(6) 0.1345(4) 0.0323(16) Uani 1 1 d .
H38A H 0.0228 0.5031 0.1103 0.039 Uiso 1 1 calc R
H38B H 0.0362 0.6208 0.1627 0.039 Uiso 1 1 calc R
C39 C 0.1541(8) 0.6394(6) 0.0657(4) 0.0356(17) Uani 1 1 d .
H39A H 0.0747 0.6460 0.0256 0.043 Uiso 1 1 calc R
H39B H 0.2030 0.5947 0.0354 0.043 Uiso 1 1 calc R
C40 C 0.2627(9) 0.7561(6) 0.1005(4) 0.0397(19) Uani 1 1 d .
H40A H 0.2126 0.8027 0.1273 0.048 Uiso 1 1 calc R
H40B H 0.3034 0.7921 0.0545 0.048 Uiso 1 1 calc R
C41 C 0.3868(8) 0.7493(6) 0.1647(4) 0.0399(19) Uani 1 1 d .
H41A H 0.4426 0.7084 0.1369 0.048 Uiso 1 1 calc R
H41B H 0.4534 0.8258 0.1885 0.048 Uiso 1 1 calc R
C42 C 0.3254(8) 0.6886(6) 0.2348(4) 0.0357(17) Uani 1 1 d .
H42A H 0.2765 0.7328 0.2657 0.043 Uiso 1 1 calc R
H42B H 0.4056 0.6819 0.2743 0.043 Uiso 1 1 calc R
C43 C 0.6464(13) -0.1039(11) 0.4044(7) 0.097(4) Uani 1 1 d .
H43A H 0.5878 -0.1658 0.4290 0.117 Uiso 1 1 calc R
H43B H 0.7400 -0.0664 0.4412 0.117 Uiso 1 1 calc R
H43C H 0.6625 -0.1333 0.3501 0.117 Uiso 1 1 calc R
C44 C 0.5672(12) -0.0204(9) 0.3932(7) 0.075(3) Uani 1 1 d .
H44A H 0.4726 -0.0598 0.3565 0.090 Uiso 1 1 calc R
H44B H 0.6242 0.0383 0.3643 0.090 Uiso 1 1 calc R
C45 C 0.5387(12) 0.0391(10) 0.4763(7) 0.085(4) Uani 1 1 d .
H45A H 0.6328 0.0866 0.5106 0.102 Uiso 1 1 calc R
H45B H 0.4828 0.0885 0.4619 0.102 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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
N1 Ni1 C2 114.3(3) .
N1 Ni1 C1 156.7(3) .
C2 Ni1 C1 42.5(3) .
N1 Ni1 C3 83.5(3) .
C2 Ni1 C3 41.3(3) .
C1 Ni1 C3 75.1(3) .
N1 Ni1 P1 101.58(18) .
C2 Ni1 P1 143.2(2) .
C1 Ni1 P1 101.7(2) .
C3 Ni1 P1 159.8(2) .
C37 P1 C31 110.9(3) .
C37 P1 C25 104.5(3) .
C31 P1 C25 104.6(3) .
C37 P1 Ni1 112.3(2) .
C31 P1 Ni1 116.5(2) .
C25 P1 Ni1 106.9(2) .
C5 N1 Ni1 120.2(5) .
C2 C1 Ni1 68.1(4) .
C3 C2 C1 118.7(7) .
C3 C2 C6 120.4(6) .
C1 C2 C6 119.7(6) .
C3 C2 Ni1 71.4(4) .
C1 C2 Ni1 69.4(4) .
C6 C2 Ni1 120.5(5) .
C2 C3 C7 121.6(6) .
C2 C3 C4 120.7(6) .
C7 C3 C4 117.2(6) .
C2 C3 Ni1 67.3(4) .
C7 C3 Ni1 103.0(5) .
C4 C3 Ni1 107.3(5) .
C5 C4 C3 109.9(6) .
N1 C5 C8 128.6(7) .
N1 C5 C4 112.0(5) .
C8 C5 C4 119.1(6) .
C20 C6 C24 118.4(6) .
C20 C6 C2 117.6(6) .
C24 C6 C2 124.0(6) .
C19 C7 C15 117.2(6) .
C19 C7 C3 121.9(6) .
C15 C7 C3 120.3(6) .
C5 C8 C9 132.0(6) .
C10 C9 C14 114.4(6) .
C10 C9 C8 119.2(6) .
C14 C9 C8 126.4(6) .
C11 C10 C9 123.5(7) .
C10 C11 C12 120.1(7) .
C13 C12 C11 118.5(7) .
C12 C13 C14 121.6(8) .
C13 C14 C9 121.8(7) .
C16 C15 C7 121.1(7) .
C17 C16 C15 120.3(7) .
C16 C17 C18 119.6(7) .
C19 C18 C17 120.3(7) .
C18 C19 C7 121.4(7) .
C6 C20 C21 120.8(7) .
C22 C21 C20 120.1(7) .
C21 C22 C23 119.4(7) .
C24 C23 C22 120.6(7) .
C23 C24 C6 120.7(7) .
C30 C25 C26 110.5(6) .
C30 C25 P1 112.0(5) .
C26 C25 P1 109.9(5) .
C25 C26 C27 111.6(6) .
C28 C27 C26 112.1(6) .
C29 C28 C27 110.7(7) .
C28 C29 C30 110.9(7) .
C25 C30 C29 110.5(6) .
C36 C31 C32 110.3(5) .
C36 C31 P1 112.4(4) .
C32 C31 P1 117.5(5) .
C33 C32 C31 111.1(6) .
C32 C33 C34 111.2(5) .
C35 C34 C33 111.0(6) .
C36 C35 C34 110.5(6) .
C35 C36 C31 111.6(5) .
C42 C37 C38 110.4(6) .
C42 C37 P1 117.3(4) .
C38 C37 P1 113.2(5) .
C39 C38 C37 109.3(6) .
C38 C39 C40 111.6(6) .
C39 C40 C41 110.8(6) .
C42 C41 C40 110.3(6) .
C41 C42 C37 110.4(6) .
C43 C44 C45 115.7(10) .
C45 C45 C44 112.3(13) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.850(6) .
Ni1 C2 1.976(7) .
Ni1 C1 1.995(7) .
Ni1 C3 2.031(8) .
Ni1 P1 2.198(2) .
P1 C37 1.842(7) .
P1 C31 1.848(6) .
P1 C25 1.866(7) .
N1 C5 1.369(8) .
C1 C2 1.438(9) .
C2 C3 1.415(10) .
C2 C6 1.511(9) .
C3 C7 1.493(9) .
C3 C4 1.516(9) .
C4 C5 1.515(9) .
C5 C8 1.375(8) .
C6 C20 1.377(10) .
C6 C24 1.383(9) .
C7 C19 1.400(9) .
C7 C15 1.403(9) .
C8 C9 1.442(9) .
C9 C10 1.402(9) .
C9 C14 1.423(10) .
C10 C11 1.373(10) .
C11 C12 1.386(10) .
C12 C13 1.371(10) .
C13 C14 1.376(10) .
C15 C16 1.382(10) .
C16 C17 1.380(11) .
C17 C18 1.382(10) .
C18 C19 1.376(9) .
C20 C21 1.389(10) .
C21 C22 1.366(10) .
C22 C23 1.377(11) .
C23 C24 1.372(10) .
C25 C30 1.522(10) .
C25 C26 1.535(10) .
C26 C27 1.537(10) .
C27 C28 1.522(11) .
C28 C29 1.521(11) .
C29 C30 1.549(10) .
C31 C36 1.534(9) .
C31 C32 1.546(9) .
C32 C33 1.529(9) .
C33 C34 1.539(10) .
C34 C35 1.536(10) .
C35 C36 1.531(9) .
C37 C42 1.548(9) .
C37 C38 1.558(9) .
C38 C39 1.525(9) .
C39 C40 1.527(10) .
C40 C41 1.543(10) .
C41 C42 1.538(9) .
C43 C44 1.525(15) .
C44 C45 1.588(15) .
C45 C45 1.42(2) 2_656
