#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/21/4072108.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_4072108
loop_
_publ_author_name
'Dyer, Philip W.'
'Fawcett, John'
'Hanton, Martin J.'
_publ_section_title
;
 RigidN-Phosphino Guanidine P,N Ligands and Their Use in Nickel-Catalyzed
 Ethylene Oligomerization
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5082
_journal_paper_doi               10.1021/om8005933
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C19 H22 Br2 N3 Ni P, 0.5(C D2 Cl2)'
_chemical_formula_sum            'C19.5 H22 Br2 Cl D N3 Ni P'
_chemical_formula_weight         585.37
_chemical_name_systematic
; 
 Diphenyl 1,5,7-triazabicyclo[4.4.0]dec-5-ene phosphine nickel 
 dibromide 
;
_chemical_temperature_decomposition_gt 240
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 127.2440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.4597(15)
_cell_length_b                   13.0822(8)
_cell_length_c                   17.0457(11)
_cell_measurement_reflns_used    9035
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.165
_cell_measurement_theta_min      2.405
_cell_volume                     4342.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16335
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    4.782
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 11008 reflections corrected using SADABS. R(int) = 0.1122 before correction. 
 R(int) = 0.0272 after correction. 
;
_exptl_crystal_colour            'deep red'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.331
_refine_diff_density_min         -1.316
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0346
_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)+(0.0710P)²+0.4016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                3691
_reflns_number_total             4264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8005933_si_001.cif
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified 'more than' ('>') a certain temperature. The value '> 240
dec.' was changed to '240' - it should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C19.50 H22 Br2 Cl D N3 Ni P'
_cod_database_code               4072108
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ni1 Ni 0.107082(18) 0.42242(3) 0.02678(3) 0.01922(12) Uani 1 1 d .
Br1 Br 0.221860(15) 0.43023(2) 0.16430(2) 0.02729(12) Uani 1 1 d .
Br2 Br 0.106309(17) 0.59523(3) -0.01115(3) 0.03722(13) Uani 1 1 d .
P1 P 0.11191(4) 0.27081(6) 0.07204(5) 0.02004(18) Uani 1 1 d .
N1 N 0.01408(12) 0.3910(2) -0.08062(18) 0.0241(6) Uani 1 1 d .
N2 N -0.08037(13) 0.2788(2) -0.1486(2) 0.0314(6) Uani 1 1 d .
N3 N 0.02833(12) 0.23480(18) -0.00720(19) 0.0245(6) Uani 1 1 d .
C1 C -0.01440(14) 0.3046(2) -0.0817(2) 0.0238(6) Uani 1 1 d .
C2 C -0.03219(16) 0.4664(3) -0.1584(2) 0.0323(7) Uani 1 1 d .
H2A H -0.0058 0.5092 -0.1709 0.039 Uiso 1 1 calc R
H2B H -0.0522 0.5100 -0.1358 0.039 Uiso 1 1 calc R
C3 C -0.08894(18) 0.4140(3) -0.2530(3) 0.0408(9) Uani 1 1 d .
H3A H -0.1195 0.4647 -0.3020 0.049 Uiso 1 1 calc R
H3B H -0.0695 0.3740 -0.2786 0.049 Uiso 1 1 calc R
C4 C -0.12798(16) 0.3459(3) -0.2327(2) 0.0384(9) Uani 1 1 d .
H4A H -0.1539 0.3870 -0.2182 0.046 Uiso 1 1 calc R
H4B H -0.1602 0.3048 -0.2905 0.046 Uiso 1 1 calc R
C5 C -0.11294(17) 0.1898(3) -0.1390(3) 0.0462(10) Uani 1 1 d .
H5A H -0.1232 0.1387 -0.1875 0.055 Uiso 1 1 calc R
H5B H -0.1560 0.2109 -0.1527 0.055 Uiso 1 1 calc R
C6 C -0.06797(17) 0.1434(3) -0.0384(3) 0.0422(9) Uani 1 1 d .
H6A H -0.0856 0.0767 -0.0390 0.051 Uiso 1 1 calc R
H6B H -0.0678 0.1864 0.0081 0.051 Uiso 1 1 calc R
C7 C 0.00400(16) 0.1329(2) -0.0073(3) 0.0314(7) Uani 1 1 d .
H7A H 0.0337 0.1031 0.0580 0.038 Uiso 1 1 calc R
H7B H 0.0042 0.0888 -0.0529 0.038 Uiso 1 1 calc R
C8 C 0.15891(14) 0.1785(2) 0.0545(2) 0.0217(6) Uani 1 1 d .
C9 C 0.18097(16) 0.0837(2) 0.1011(2) 0.0253(7) Uani 1 1 d .
H9 H 0.1734 0.0658 0.1466 0.030 Uiso 1 1 calc R
C10 C 0.21439(16) 0.0150(2) 0.0800(2) 0.0297(7) Uani 1 1 d .
H10 H 0.2298 -0.0476 0.1123 0.036 Uiso 1 1 calc R
C11 C 0.22437(18) 0.0411(3) 0.0108(3) 0.0349(8) Uani 1 1 d .
H11 H 0.2462 -0.0043 -0.0040 0.042 Uiso 1 1 calc R
C12 C 0.2019(2) 0.1344(3) -0.0362(3) 0.0443(9) Uani 1 1 d .
H12 H 0.2082 0.1511 -0.0832 0.053 Uiso 1 1 calc R
C13 C 0.17002(18) 0.2033(3) -0.0144(3) 0.0366(8) Uani 1 1 d .
H13 H 0.1559 0.2665 -0.0458 0.044 Uiso 1 1 calc R
C14 C 0.13139(15) 0.2482(2) 0.1914(2) 0.0245(6) Uani 1 1 d .
C15 C 0.19562(15) 0.2129(2) 0.2720(2) 0.0257(7) Uani 1 1 d .
H15 H 0.2295 0.1983 0.2646 0.031 Uiso 1 1 calc R
C16 C 0.20911(17) 0.1996(3) 0.3631(2) 0.0355(8) Uani 1 1 d .
H16 H 0.2512 0.1737 0.4160 0.043 Uiso 1 1 calc R
C17 C 0.1594(2) 0.2252(3) 0.3746(3) 0.0451(9) Uani 1 1 d .
H17 H 0.1682 0.2169 0.4355 0.054 Uiso 1 1 calc R
C18 C 0.09645(19) 0.2633(3) 0.2954(3) 0.0461(10) Uani 1 1 d .
H18 H 0.0638 0.2822 0.3040 0.055 Uiso 1 1 calc R
C19 C 0.08194(17) 0.2733(3) 0.2043(2) 0.0335(8) Uani 1 1 d .
H19 H 0.0391 0.2968 0.1512 0.040 Uiso 1 1 calc R
Cl1 Cl 0.0000 0.15857(18) 0.7500 0.1422(13) Uani 1 2 d S
Cl2 Cl -0.02606(19) -0.0417(3) 0.7698(3) 0.0994(10) Uani 0.50 1 d P
C20 C 0.0415(5) 0.0328(8) 0.7986(8) 0.061(2) Uani 0.50 1 d P
D20A D 0.0764(5) 0.0370(8) 0.8686(8) 0.073 Uiso 0.50 1 d PR
D20B D 0.0620(5) 0.0100(8) 0.7682(8) 0.073 Uiso 0.50 1 d PR
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'
D D 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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 P1 85.32(8) . . y
N1 Ni1 Br1 169.89(8) . . y
P1 Ni1 Br1 84.63(2) . . y
N1 Ni1 Br2 97.87(8) . . y
P1 Ni1 Br2 175.66(3) . . y
Br1 Ni1 Br2 92.225(16) . . y
N3 P1 C14 102.71(14) . . ?
N3 P1 C8 105.22(13) . . ?
C14 P1 C8 108.35(14) . . ?
N3 P1 Ni1 101.32(9) . . ?
C14 P1 Ni1 118.94(10) . . ?
C8 P1 Ni1 117.86(10) . . ?
C1 N1 C2 116.5(3) . . ?
C1 N1 Ni1 120.6(2) . . ?
C2 N1 Ni1 122.4(2) . . ?
C1 N2 C5 123.9(3) . . ?
C1 N2 C4 121.0(3) . . ?
C5 N2 C4 114.7(3) . . ?
C1 N3 C7 121.2(2) . . ?
C1 N3 P1 115.0(2) . . ?
C7 N3 P1 123.2(2) . . ?
N1 C1 N2 125.5(3) . . y
N1 C1 N3 116.8(3) . . y
N2 C1 N3 117.7(3) . . y
N1 C2 C3 111.3(3) . . ?
C4 C3 C2 109.1(3) . . ?
N2 C4 C3 110.0(3) . . ?
N2 C5 C6 112.1(3) . . ?
C5 C6 C7 109.4(3) . . ?
N3 C7 C6 107.8(3) . . ?
C13 C8 C9 118.8(3) . . ?
C13 C8 P1 116.8(2) . . ?
C9 C8 P1 124.3(2) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 119.5(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C12 C11 120.9(3) . . ?
C12 C13 C8 120.3(3) . . ?
C19 C14 C15 119.2(3) . . ?
C19 C14 P1 118.4(2) . . ?
C15 C14 P1 122.2(2) . . ?
C16 C15 C14 120.3(3) . . ?
C17 C16 C15 119.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
C19 C18 C17 120.7(3) . . ?
C18 C19 C14 120.1(3) . . ?
C20 Cl1 C20 53.9(6) 2_556 . ?
D20B Cl2 C20 43.9(4) 2_556 2_556 ?
D20B Cl2 C20 96.9(9) 2_556 . ?
C20 Cl2 C20 64.3(7) 2_556 . ?
D20B Cl2 Cl2 108.2(6) 2_556 2_556 ?
C20 Cl2 Cl2 64.6(4) 2_556 2_556 ?
C20 Cl2 Cl2 46.8(4) . 2_556 ?
D20B C20 D20A 109.2 . . ?
D20B C20 Cl2 45.0(4) . 2_556 ?
D20A C20 Cl2 132.1(4) . 2_556 ?
D20B C20 C20 100.5(6) . 2_556 ?
D20A C20 C20 149.7(6) . 2_556 ?
Cl2 C20 C20 67.5(6) 2_556 2_556 ?
D20B C20 Cl2 113.3(3) . . ?
D20A C20 Cl2 111.4(4) . . ?
Cl2 C20 Cl2 68.6(5) 2_556 . ?
C20 C20 Cl2 48.2(4) 2_556 . ?
D20B C20 Cl1 111.1(3) . . ?
D20A C20 Cl1 109.9(3) . . ?
Cl2 C20 Cl1 117.0(7) 2_556 . ?
C20 C20 Cl1 63.1(3) 2_556 . ?
Cl2 C20 Cl1 101.8(5) . . ?
C20 D20B Cl2 91.1(6) . 2_556 ?
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 1.912(2) . y
Ni1 P1 2.1054(8) . y
Ni1 Br1 2.3283(5) . y
Ni1 Br2 2.3483(5) . y
P1 N3 1.698(2) . y
P1 C14 1.810(3) . ?
P1 C8 1.812(3) . ?
N1 C1 1.322(4) . y
N1 C2 1.482(4) . ?
N2 C1 1.338(4) . y
N2 C5 1.475(4) . ?
N2 C4 1.470(4) . ?
N3 C1 1.390(4) . y
N3 C7 1.459(4) . ?
C2 C3 1.512(5) . ?
C3 C4 1.491(5) . ?
C5 C6 1.495(5) . ?
C6 C7 1.506(4) . ?
C8 C13 1.394(4) . ?
C8 C9 1.394(4) . ?
C9 C10 1.399(4) . ?
C10 C11 1.384(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.381(5) . ?
C14 C19 1.394(4) . ?
C14 C15 1.399(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.384(5) . ?
C17 C18 1.388(5) . ?
C18 C19 1.373(5) . ?
Cl1 C20 1.846(11) 2_556 ?
Cl1 C20 1.846(11) . ?
Cl2 D20B 0.980(10) 2_556 ?
Cl2 C20 1.385(10) 2_556 ?
Cl2 C20 1.716(9) . ?
Cl2 Cl2 1.768(7) 2_556 ?
C20 D20B 0.9600 . ?
C20 D20A 0.9600 . ?
C20 Cl2 1.385(10) 2_556 ?
C20 C20 1.673(19) 2_556 ?
D20B Cl2 0.980(10) 2_556 ?
