#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:25:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179843 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/39/7013935.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_7013935
loop_
_publ_author_name
'Phan, Nam T. S.'
'Brown, David H.'
'Adams, Harry'
'Spey, Sharon E.'
'Styring, Peter'
_publ_section_title
;
 Solid-supported cross-coupling catalysts derived from homogeneous
 nickel and palladium coordination complexes.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1348
_journal_page_last               1357
_journal_paper_doi               10.1039/b316553c
_journal_year                    2004
_chemical_formula_sum            'C16 H24 N2 Ni O5'
_chemical_formula_weight         383.08
_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                101.786(4)
_cell_angle_beta                 99.434(4)
_cell_angle_gamma                95.531(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4282(16)
_cell_length_b                   9.916(2)
_cell_length_c                   12.270(3)
_cell_measurement_reflns_used    2909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      46.711
_cell_measurement_theta_min      4.827
_cell_volume                     864.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3847
_diffrn_reflns_theta_full        23.36
_diffrn_reflns_theta_max         23.36
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    1.149
_exptl_absorpt_correction_T_max  0.7099
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0607
_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)+(0.1181P)²+2.0085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2254
_reflns_number_total             2484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b316553c.txt
_cod_data_source_block           psty1m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        864.9(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7013935
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.13010(7) 0.41722(5) 0.32807(5) 0.0235(3) Uani 1 1 d . . .
N1 N 0.2233(5) 0.5326(4) 0.4696(3) 0.0254(9) Uani 1 1 d . . .
N2 N 0.0600(6) 0.5736(4) 0.2836(3) 0.0266(9) Uani 1 1 d . . .
O1 O 0.1894(5) 0.2556(3) 0.3684(3) 0.0292(8) Uani 1 1 d . . .
O2 O 0.0395(5) 0.3010(3) 0.1869(3) 0.0275(8) Uani 1 1 d . . .
O3 O -0.3489(5) 0.1374(3) -0.1742(3) 0.0355(8) Uani 1 1 d . . .
H3A H -0.3241 0.0623 -0.1621 0.053 Uiso 1 1 calc R . .
C1 C 0.1888(7) 0.6775(5) 0.4792(4) 0.0299(11) Uani 1 1 d . . .
H1A H 0.2955 0.7400 0.5244 0.036 Uiso 1 1 calc R . .
H1B H 0.0841 0.6934 0.5158 0.036 Uiso 1 1 calc R . .
C2 C 0.1502(7) 0.7040(5) 0.3614(4) 0.0329(11) Uani 1 1 d . . .
H2A H 0.0707 0.7758 0.3590 0.039 Uiso 1 1 calc R . .
H2B H 0.2643 0.7347 0.3396 0.039 Uiso 1 1 calc R . .
C3 C -0.0524(7) 0.5784(5) 0.1926(4) 0.0283(11) Uani 1 1 d . . .
H3B H -0.0842 0.6648 0.1848 0.034 Uiso 1 1 calc R . .
C4 C -0.1319(6) 0.4606(5) 0.1029(4) 0.0258(10) Uani 1 1 d . . .
C5 C -0.2588(7) 0.4775(5) 0.0101(4) 0.0318(11) Uani 1 1 d . . .
H5A H -0.2955 0.5646 0.0106 0.038 Uiso 1 1 calc R . .
C6 C -0.3301(7) 0.3711(5) -0.0805(4) 0.0323(11) Uani 1 1 d . . .
H6A H -0.4145 0.3853 -0.1406 0.039 Uiso 1 1 calc R . .
C7 C -0.2747(6) 0.2398(5) -0.0820(4) 0.0274(10) Uani 1 1 d . . .
C8 C -0.1466(7) 0.2190(5) 0.0077(4) 0.0277(11) Uani 1 1 d . . .
H8A H -0.1073 0.1323 0.0043 0.033 Uiso 1 1 calc R . .
C9 C -0.0764(6) 0.3268(5) 0.1025(4) 0.0258(10) Uani 1 1 d . . .
C10 C 0.2723(7) 0.2439(5) 0.4674(4) 0.0293(11) Uani 1 1 d . . .
C11 C 0.3269(7) 0.3521(5) 0.5590(4) 0.0301(11) Uani 1 1 d . . .
H11A H 0.3847 0.3324 0.6261 0.036 Uiso 1 1 calc R . .
C12 C 0.3024(6) 0.4930(5) 0.5602(4) 0.0285(11) Uani 1 1 d . . .
C13 C 0.3671(7) 0.5973(5) 0.6712(4) 0.0337(12) Uani 1 1 d . . .
H13A H 0.3432 0.6880 0.6615 0.051 Uiso 1 1 calc R . .
H13B H 0.4969 0.5985 0.6957 0.051 Uiso 1 1 calc R . .
H13C H 0.3024 0.5719 0.7272 0.051 Uiso 1 1 calc R . .
C14 C 0.3003(8) 0.0974(5) 0.4751(5) 0.0413(13) Uani 1 1 d . . .
H14A H 0.2534 0.0356 0.4026 0.062 Uiso 1 1 calc R . .
H14B H 0.2360 0.0705 0.5307 0.062 Uiso 1 1 calc R . .
H14C H 0.4293 0.0928 0.4967 0.062 Uiso 1 1 calc R . .
O1S O -0.2800(6) -0.1087(4) -0.1462(3) 0.0456(10) Uani 1 1 d . . .
H1S H -0.2147 -0.1629 -0.1743 0.055 Uiso 1 1 calc R . .
O2S O -0.7446(7) 0.1324(5) -0.2322(5) 0.0675(13) Uani 1 1 d . . .
H2S H -0.6321 0.1367 -0.2189 0.081 Uiso 1 1 calc R . .
C1S C -0.3644(9) -0.1654(6) -0.0690(5) 0.0460(14) Uani 1 1 d . . .
H1S1 H -0.2719 -0.1772 -0.0085 0.069 Uiso 1 1 calc R . .
H1S2 H -0.4341 -0.2540 -0.1068 0.069 Uiso 1 1 calc R . .
H1S3 H -0.4452 -0.1039 -0.0387 0.069 Uiso 1 1 calc R . .
C2S C -0.8229(13) -0.0030(6) -0.2456(6) 0.077(2) Uani 1 1 d . . .
H2S1 H -0.7853 -0.0342 -0.1773 0.116 Uiso 1 1 calc R . .
H2S2 H -0.7833 -0.0611 -0.3075 0.116 Uiso 1 1 calc R . .
H2S3 H -0.9546 -0.0082 -0.2614 0.116 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'
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'
Ni Ni 0.3393 1.1124 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 O1 177.14(15) . . ?
N2 Ni1 O2 93.97(16) . . ?
O1 Ni1 O2 83.83(14) . . ?
N2 Ni1 N1 86.54(17) . . ?
O1 Ni1 N1 95.68(16) . . ?
O2 Ni1 N1 179.31(15) . . ?
C12 N1 C1 119.6(4) . . ?
C12 N1 Ni1 125.9(3) . . ?
C1 N1 Ni1 114.4(3) . . ?
C3 N2 C2 119.2(4) . . ?
C3 N2 Ni1 127.1(3) . . ?
C2 N2 Ni1 113.7(3) . . ?
C10 O1 Ni1 126.6(3) . . ?
C9 O2 Ni1 127.5(3) . . ?
N1 C1 C2 108.2(4) . . ?
N2 C2 C1 107.9(4) . . ?
N2 C3 C4 125.0(4) . . ?
C5 C4 C9 118.8(4) . . ?
C5 C4 C3 119.9(4) . . ?
C9 C4 C3 121.2(4) . . ?
C6 C5 C4 122.4(4) . . ?
C5 C6 C7 119.1(5) . . ?
O3 C7 C8 122.7(4) . . ?
O3 C7 C6 116.9(4) . . ?
C8 C7 C6 120.4(4) . . ?
C7 C8 C9 120.9(4) . . ?
O2 C9 C8 118.8(4) . . ?
O2 C9 C4 122.9(4) . . ?
C8 C9 C4 118.4(4) . . ?
O1 C10 C11 124.2(4) . . ?
O1 C10 C14 114.4(4) . . ?
C11 C10 C14 121.3(5) . . ?
C10 C11 C12 125.1(5) . . ?
N1 C12 C11 122.5(4) . . ?
N1 C12 C13 120.4(4) . . ?
C11 C12 C13 117.1(4) . . ?
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 1.839(4) . ?
Ni1 O1 1.843(3) . ?
Ni1 O2 1.853(3) . ?
Ni1 N1 1.856(4) . ?
N1 C12 1.320(7) . ?
N1 C1 1.468(6) . ?
N2 C3 1.292(7) . ?
N2 C2 1.467(6) . ?
O1 C10 1.302(6) . ?
O2 C9 1.319(6) . ?
O3 C7 1.355(6) . ?
C1 C2 1.509(7) . ?
C3 C4 1.433(7) . ?
C4 C5 1.403(7) . ?
C4 C9 1.427(7) . ?
C5 C6 1.360(7) . ?
C6 C7 1.400(7) . ?
C7 C8 1.395(7) . ?
C8 C9 1.397(7) . ?
C10 C11 1.361(7) . ?
C10 C14 1.506(7) . ?
C11 C12 1.424(7) . ?
C12 C13 1.507(7) . ?
O1S C1S 1.396(7) . ?
O2S C2S 1.377(7) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ni1 N1 C12 178.3(4) . . . . ?
O1 Ni1 N1 C12 0.1(4) . . . . ?
O2 Ni1 N1 C12 -44(12) . . . . ?
N2 Ni1 N1 C1 3.5(3) . . . . ?
O1 Ni1 N1 C1 -174.7(3) . . . . ?
O2 Ni1 N1 C1 142(12) . . . . ?
O1 Ni1 N2 C3 -25(3) . . . . ?
O2 Ni1 N2 C3 14.4(4) . . . . ?
N1 Ni1 N2 C3 -166.0(4) . . . . ?
O1 Ni1 N2 C2 157(3) . . . . ?
O2 Ni1 N2 C2 -163.7(3) . . . . ?
N1 Ni1 N2 C2 15.9(3) . . . . ?
N2 Ni1 O1 C10 -142(3) . . . . ?
O2 Ni1 O1 C10 178.7(4) . . . . ?
N1 Ni1 O1 C10 -0.8(4) . . . . ?
N2 Ni1 O2 C9 -15.9(4) . . . . ?
O1 Ni1 O2 C9 162.3(4) . . . . ?
N1 Ni1 O2 C9 -154(12) . . . . ?
C12 N1 C1 C2 164.0(4) . . . . ?
Ni1 N1 C1 C2 -20.9(5) . . . . ?
C3 N2 C2 C1 151.2(4) . . . . ?
Ni1 N2 C2 C1 -30.5(5) . . . . ?
N1 C1 C2 N2 31.6(5) . . . . ?
C2 N2 C3 C4 171.9(4) . . . . ?
Ni1 N2 C3 C4 -6.1(7) . . . . ?
N2 C3 C4 C5 177.3(5) . . . . ?
N2 C3 C4 C9 -6.4(7) . . . . ?
C9 C4 C5 C6 -0.4(7) . . . . ?
C3 C4 C5 C6 176.0(4) . . . . ?
C4 C5 C6 C7 -0.3(7) . . . . ?
C5 C6 C7 O3 -179.7(4) . . . . ?
C5 C6 C7 C8 -0.7(7) . . . . ?
O3 C7 C8 C9 -178.6(4) . . . . ?
C6 C7 C8 C9 2.5(7) . . . . ?
Ni1 O2 C9 C8 -171.9(3) . . . . ?
Ni1 O2 C9 C4 8.9(6) . . . . ?
C7 C8 C9 O2 177.7(4) . . . . ?
C7 C8 C9 C4 -3.1(7) . . . . ?
C5 C4 C9 O2 -178.8(4) . . . . ?
C3 C4 C9 O2 4.9(7) . . . . ?
C5 C4 C9 C8 2.1(6) . . . . ?
C3 C4 C9 C8 -174.3(4) . . . . ?
Ni1 O1 C10 C11 1.0(7) . . . . ?
Ni1 O1 C10 C14 179.4(3) . . . . ?
O1 C10 C11 C12 -0.2(8) . . . . ?
C14 C10 C11 C12 -178.6(5) . . . . ?
C1 N1 C12 C11 175.0(4) . . . . ?
Ni1 N1 C12 C11 0.4(6) . . . . ?
C1 N1 C12 C13 -3.6(6) . . . . ?
Ni1 N1 C12 C13 -178.1(3) . . . . ?
C10 C11 C12 N1 -0.5(8) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
