#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:03:15 +0100 (vie 25 de mar de 2016) $
#$Revision: 179738 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/34/7003433.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_7003433
loop_
_publ_author_name
'Kermagoret, Anthony'
'Braunstein, Pierre'
_publ_section_title
;
 Synthesis of nickel complexes with bidentate N,O-type ligands and
 application in the catalytic oligomerization of ethylene
;
_journal_issue                   12
_journal_name_full               'Dalton Transactions'
_journal_page_first              1564
_journal_page_last               1573
_journal_paper_doi               10.1039/b716111e
_journal_year                    2008
_chemical_formula_moiety         'C18 H21 N3 Ni O3, C H2 Cl2, 2 (Cl)'
_chemical_formula_sum            'C19 H23 Cl4 N3 Ni O3'
_chemical_formula_weight         541.91
_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                91.790(2)
_cell_angle_beta                 113.320(2)
_cell_angle_gamma                118.250(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9430(4)
_cell_length_b                   11.3560(4)
_cell_length_c                   12.3210(5)
_cell_measurement_reflns_used    12347
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1192.48(9)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0943
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15347
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1448
_reflns_number_gt                4133
_reflns_number_total             6929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b716111e.txt
_cod_data_source_block           3
_cod_original_cell_volume        1192.48(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7003433
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 0.49743(4) 0.80661(4) 0.29379(3) 0.02659(12) Uani 1 1 d . . .
Cl1 Cl 0.66402(9) 0.51473(9) 0.28686(7) 0.0459(2) Uani 1 1 d . . .
Cl2 Cl 0.70760(8) 0.94663(8) 0.68916(6) 0.0393(2) Uani 1 1 d . . .
Cl3 Cl 0.86890(15) 0.67786(15) -0.14704(16) 0.1222(6) Uani 1 1 d . . .
Cl4 Cl 0.84862(17) 0.80503(16) 0.04391(10) 0.1049(5) Uani 1 1 d . . .
O1 O 0.4839(2) 0.6470(2) 0.19795(16) 0.0371(5) Uani 1 1 d . . .
HO1 H 0.5399 0.6131 0.2257 0.056 Uiso 1 1 calc . . .
O2 O 0.57123(19) 0.7448(2) 0.45190(16) 0.0315(5) Uani 1 1 d . . .
HO2 H 0.6183 0.8051 0.5186 0.047 Uiso 1 1 calc . . .
O3 O 0.52951(19) 0.97720(19) 0.39058(16) 0.0295(4) Uani 1 1 d . . .
HO3 H 0.4597 0.9957 0.3759 0.044 Uiso 1 1 calc . . .
N1 N 0.4048(2) 0.8234(2) 0.11800(19) 0.0286(5) Uani 1 1 d . . .
N2 N 0.2840(2) 0.6830(2) 0.2946(2) 0.0281(5) Uani 1 1 d . . .
N3 N 0.7286(2) 0.9538(2) 0.34092(19) 0.0288(5) Uani 1 1 d . . .
C1 C 0.4397(4) 0.6349(3) 0.0711(3) 0.0426(8) Uani 1 1 d . . .
H1A H 0.3519 0.5391 0.0224 0.051 Uiso 1 1 calc . . .
H1B H 0.5293 0.6544 0.0563 0.051 Uiso 1 1 calc . . .
C2 C 0.3905(3) 0.7357(3) 0.0319(2) 0.0307(6) Uani 1 1 d . . .
C3 C 0.3300(3) 0.7349(3) -0.0916(2) 0.0384(7) Uani 1 1 d . . .
H3 H 0.3233 0.6735 -0.1509 0.046 Uiso 1 1 calc . . .
C4 C 0.2803(4) 0.8252(4) -0.1253(3) 0.0462(9) Uani 1 1 d . . .
H4 H 0.2369 0.8254 -0.2090 0.055 Uiso 1 1 calc . . .
C5 C 0.2935(3) 0.9151(3) -0.0378(3) 0.0400(8) Uani 1 1 d . . .
H5 H 0.2598 0.9779 -0.0598 0.048 Uiso 1 1 calc . . .
C6 C 0.3572(3) 0.9115(3) 0.0832(2) 0.0329(7) Uani 1 1 d . . .
H6 H 0.3677 0.9740 0.1440 0.039 Uiso 1 1 calc . . .
C7 C 0.4436(3) 0.6211(3) 0.4512(3) 0.0361(7) Uani 1 1 d . . .
H7A H 0.4631 0.6199 0.5367 0.043 Uiso 1 1 calc . . .
H7B H 0.4366 0.5387 0.4130 0.043 Uiso 1 1 calc . . .
C8 C 0.2907(3) 0.6141(3) 0.3809(2) 0.0296(6) Uani 1 1 d . . .
C9 C 0.1651(3) 0.5395(3) 0.4040(3) 0.0357(7) Uani 1 1 d . . .
H9 H 0.1738 0.4923 0.4663 0.043 Uiso 1 1 calc . . .
C10 C 0.0270(3) 0.5343(3) 0.3352(3) 0.0397(7) Uani 1 1 d . . .
H10 H -0.0613 0.4830 0.3488 0.048 Uiso 1 1 calc . . .
C11 C 0.0200(3) 0.6054(3) 0.2464(3) 0.0400(8) Uani 1 1 d . . .
H11 H -0.0734 0.6042 0.1983 0.048 Uiso 1 1 calc . . .
C12 C 0.1492(3) 0.6779(3) 0.2280(3) 0.0348(7) Uani 1 1 d . . .
H12 H 0.1431 0.7261 0.1663 0.042 Uiso 1 1 calc . . .
C13 C 0.6785(3) 1.1028(3) 0.4389(2) 0.0314(6) Uani 1 1 d . . .
H13A H 0.7218 1.1358 0.5287 0.038 Uiso 1 1 calc . . .
H13B H 0.6670 1.1752 0.4014 0.038 Uiso 1 1 calc . . .
C14 C 0.7880(3) 1.0788(3) 0.4123(2) 0.0286(6) Uani 1 1 d . . .
C15 C 0.9456(3) 1.1833(3) 0.4593(3) 0.0356(7) Uani 1 1 d . . .
H15 H 0.9872 1.2692 0.5133 0.043 Uiso 1 1 calc . . .
C16 C 1.0398(3) 1.1595(4) 0.4259(3) 0.0415(8) Uani 1 1 d . . .
H16 H 1.1466 1.2303 0.4546 0.050 Uiso 1 1 calc . . .
C17 C 0.9783(3) 1.0324(4) 0.3506(3) 0.0409(8) Uani 1 1 d . . .
H17 H 1.0412 1.0146 0.3258 0.049 Uiso 1 1 calc . . .
C18 C 0.8236(3) 0.9317(3) 0.3122(3) 0.0354(7) Uani 1 1 d . . .
H18 H 0.7824 0.8427 0.2633 0.042 Uiso 1 1 calc . . .
C19 C 0.7754(4) 0.7497(4) -0.1122(3) 0.0656(11) Uani 1 1 d . . .
H19A H 0.7894 0.8294 -0.1477 0.079 Uiso 1 1 calc . . .
H19B H 0.6616 0.6797 -0.1497 0.079 Uiso 1 1 calc . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
N1 Ni1 N3 95.63(8) . . ?
N1 Ni1 N2 96.41(8) . . ?
N3 Ni1 N2 164.65(9) . . ?
C1 O1 HO1 109.5 . . ?
C7 O2 HO2 109.5 . . ?
C13 O3 HO3 109.5 . . ?
C2 N1 C6 118.4(2) . . ?
C2 N1 Ni1 115.39(19) . . ?
C6 N1 Ni1 126.2(2) . . ?
C8 N2 C12 118.2(2) . . ?
C8 N2 Ni1 114.39(17) . . ?
C12 N2 Ni1 126.97(18) . . ?
C18 N3 C14 118.5(2) . . ?
C18 N3 Ni1 125.6(2) . . ?
C14 N3 Ni1 115.77(18) . . ?
O1 C1 C2 109.5(3) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C3 122.1(3) . . ?
N1 C2 C1 118.1(2) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.8(3) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
O2 C7 C8 110.8(2) . . ?
O2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 122.4(3) . . ?
N2 C8 C7 116.0(2) . . ?
C9 C8 C7 121.6(2) . . ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 118.6(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N2 C12 C11 122.2(3) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
O3 C13 C14 109.8(2) . . ?
O3 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O3 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C15 121.6(3) . . ?
N3 C14 C13 117.5(2) . . ?
C15 C14 C13 120.8(3) . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
N3 C18 C17 122.8(3) . . ?
N3 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
Cl4 C19 Cl3 111.6(2) . . ?
Cl4 C19 H19A 109.3 . . ?
Cl3 C19 H19A 109.3 . . ?
Cl4 C19 H19B 109.3 . . ?
Cl3 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
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 N1 2.055(2) . ?
Ni1 N3 2.075(2) . ?
Ni1 N2 2.083(2) . ?
Cl3 C19 1.736(5) . ?
Cl4 C19 1.722(4) . ?
O1 C1 1.421(3) . ?
O1 HO1 0.8400 . ?
O2 C7 1.434(3) . ?
O2 HO2 0.8400 . ?
O3 C13 1.423(3) . ?
O3 HO3 0.8400 . ?
N1 C2 1.340(4) . ?
N1 C6 1.341(4) . ?
N2 C8 1.339(3) . ?
N2 C12 1.346(3) . ?
N3 C18 1.342(4) . ?
N3 C14 1.344(4) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.397(4) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.510(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.381(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.495(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
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
N3 Ni1 N1 C2 91.63(19) . . . . ?
N2 Ni1 N1 C2 -97.92(18) . . . . ?
N3 Ni1 N1 C6 -89.1(2) . . . . ?
N2 Ni1 N1 C6 81.3(2) . . . . ?
N1 Ni1 N2 C8 160.7(2) . . . . ?
N3 Ni1 N2 C8 -57.9(4) . . . . ?
N1 Ni1 N2 C12 -26.9(3) . . . . ?
N3 Ni1 N2 C12 114.5(4) . . . . ?
N1 Ni1 N3 C18 -81.2(2) . . . . ?
N2 Ni1 N3 C18 137.3(3) . . . . ?
N1 Ni1 N3 C14 102.87(19) . . . . ?
N2 Ni1 N3 C14 -38.6(4) . . . . ?
C6 N1 C2 C3 0.9(4) . . . . ?
Ni1 N1 C2 C3 -179.8(2) . . . . ?
C6 N1 C2 C1 -178.3(2) . . . . ?
Ni1 N1 C2 C1 1.0(3) . . . . ?
O1 C1 C2 N1 4.3(4) . . . . ?
O1 C1 C2 C3 -174.9(2) . . . . ?
N1 C2 C3 C4 -1.6(4) . . . . ?
C1 C2 C3 C4 177.5(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C2 N1 C6 C5 0.3(4) . . . . ?
Ni1 N1 C6 C5 -178.9(2) . . . . ?
C4 C5 C6 N1 -0.7(4) . . . . ?
C12 N2 C8 C9 -0.5(4) . . . . ?
Ni1 N2 C8 C9 172.7(2) . . . . ?
C12 N2 C8 C7 178.9(3) . . . . ?
Ni1 N2 C8 C7 -7.9(3) . . . . ?
O2 C7 C8 N2 25.7(4) . . . . ?
O2 C7 C8 C9 -155.0(3) . . . . ?
N2 C8 C9 C10 0.6(5) . . . . ?
C7 C8 C9 C10 -178.7(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C8 N2 C12 C11 0.4(4) . . . . ?
Ni1 N2 C12 C11 -171.8(2) . . . . ?
C10 C11 C12 N2 -0.4(5) . . . . ?
C18 N3 C14 C15 -1.8(4) . . . . ?
Ni1 N3 C14 C15 174.43(19) . . . . ?
C18 N3 C14 C13 177.6(2) . . . . ?
Ni1 N3 C14 C13 -6.1(3) . . . . ?
O3 C13 C14 N3 6.0(3) . . . . ?
O3 C13 C14 C15 -174.5(2) . . . . ?
N3 C14 C15 C16 3.6(4) . . . . ?
C13 C14 C15 C16 -175.9(3) . . . . ?
C14 C15 C16 C17 -2.1(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C14 N3 C18 C17 -1.4(4) . . . . ?
Ni1 N3 C18 C17 -177.2(2) . . . . ?
C16 C17 C18 N3 2.7(5) . . . . ?
