#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:14:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178554 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/62/4066291.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_4066291
loop_
_publ_author_name
'Higgs, Andrew T.'
'Zinn, Paul J.'
'Sanford, Melanie S.'
_publ_section_title
;
 Synthesis and Reactivity of NiII(Phpy)2(Phpy = 2-Phenylpyridine)†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5446
_journal_paper_doi               10.1021/om100387z
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C52 H48 Ni P4, 2(C H Cl3), 2(Br)'
_chemical_formula_sum            'C54 H50 Br2 Cl6 Ni P4'
_chemical_formula_weight         1254.05
_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                64.596(5)
_cell_angle_beta                 84.809(6)
_cell_angle_gamma                77.073(5)
_cell_formula_units_Z            1
_cell_length_a                   9.8825(2)
_cell_length_b                   12.0388(2)
_cell_length_c                   12.8023(9)
_cell_measurement_reflns_used    13204
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.80
_cell_volume                     1340.96(12)
_computing_cell_refinement       'CrystalClear-SM Expert 7.0r5'
_computing_data_collection
'CrystalClear-SM Expert 7.0r5 (Rigaku, (2010)'
_computing_data_reduction        'CrystalClear-SM Expert 7.0r5'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Saturn 944+ CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20923
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         3.82
_exptl_absorpt_coefficient_mu    6.429
_exptl_absorpt_correction_T_max  0.7393
_exptl_absorpt_correction_T_min  0.3596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Jacobson, R. (1998) Private Communication
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0358
_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)+(0.0504P)²+2.5753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                4174
_reflns_number_total             4401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100387z_si_001.cif
_cod_data_source_block           ah6107y
_cod_original_cell_volume        1340.96(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4066291
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
Br1 Br 0.92532(3) 0.75332(3) 0.21592(3) 0.02138(12) Uani 1 1 d .
Ni1 Ni 0.5000 1.0000 0.0000 0.01269(17) Uani 1 2 d S
P1 P 0.36957(7) 1.03665(7) 0.13924(7) 0.01508(18) Uani 1 1 d .
P2 P 0.35850(7) 0.86985(7) 0.02334(6) 0.01355(17) Uani 1 1 d .
Cl1 Cl -0.07994(13) 0.83494(12) 0.54168(12) 0.0593(4) Uani 1 1 d .
Cl2 Cl 0.00427(11) 0.56717(11) 0.60689(9) 0.0460(3) Uani 1 1 d .
Cl3 Cl 0.18708(9) 0.72994(11) 0.47356(8) 0.0428(3) Uani 1 1 d .
C1 C 0.3071(3) 1.1981(3) 0.1190(3) 0.0192(6) Uani 1 1 d .
C2 C 0.2086(3) 1.2756(3) 0.0320(3) 0.0251(7) Uani 1 1 d .
H2A H 0.1768 1.2434 -0.0151 0.030 Uiso 1 1 calc R
C3 C 0.1576(4) 1.3992(3) 0.0145(3) 0.0314(8) Uani 1 1 d .
H3A H 0.0936 1.4527 -0.0466 0.038 Uiso 1 1 calc R
C4 C 0.1998(4) 1.4450(3) 0.0859(3) 0.0343(9) Uani 1 1 d .
H4A H 0.1622 1.5290 0.0754 0.041 Uiso 1 1 calc R
C5 C 0.2963(4) 1.3691(3) 0.1720(3) 0.0347(9) Uani 1 1 d .
H5A H 0.3246 1.4009 0.2210 0.042 Uiso 1 1 calc R
C6 C 0.3526(4) 1.2461(3) 0.1878(3) 0.0261(7) Uani 1 1 d .
H6A H 0.4219 1.1952 0.2453 0.031 Uiso 1 1 calc R
C7 C 0.4485(3) 0.9540(3) 0.2816(3) 0.0183(6) Uani 1 1 d .
C8 C 0.3727(3) 0.9593(3) 0.3774(3) 0.0238(7) Uani 1 1 d .
H8A H 0.2828 1.0116 0.3668 0.029 Uiso 1 1 calc R
C9 C 0.4279(4) 0.8886(3) 0.4881(3) 0.0270(7) Uani 1 1 d .
H9A H 0.3768 0.8938 0.5530 0.032 Uiso 1 1 calc R
C10 C 0.5574(4) 0.8108(3) 0.5036(3) 0.0296(8) Uani 1 1 d .
H10A H 0.5948 0.7616 0.5793 0.036 Uiso 1 1 calc R
C11 C 0.6335(3) 0.8040(3) 0.4091(3) 0.0284(8) Uani 1 1 d .
H11A H 0.7222 0.7496 0.4204 0.034 Uiso 1 1 calc R
C12 C 0.5797(3) 0.8766(3) 0.2984(3) 0.0220(7) Uani 1 1 d .
H12A H 0.6328 0.8736 0.2336 0.026 Uiso 1 1 calc R
C13 C 0.2067(3) 0.9779(3) 0.1555(3) 0.0194(7) Uani 1 1 d .
H13A H 0.2095 0.9023 0.2294 0.023 Uiso 1 1 calc R
H13B H 0.1265 1.0431 0.1575 0.023 Uiso 1 1 calc R
C14 C 0.1886(3) 0.9455(3) 0.0559(3) 0.0168(6) Uani 1 1 d .
H14A H 0.1510 1.0227 -0.0128 0.020 Uiso 1 1 calc R
H14B H 0.1230 0.8880 0.0777 0.020 Uiso 1 1 calc R
C15 C 0.3181(3) 0.8173(3) -0.0819(3) 0.0186(6) Uani 1 1 d .
C16 C 0.2259(3) 0.8992(3) -0.1726(3) 0.0247(7) Uani 1 1 d .
H16A H 0.1904 0.9833 -0.1827 0.030 Uiso 1 1 calc R
C17 C 0.1865(4) 0.8559(4) -0.2480(3) 0.0329(8) Uani 1 1 d .
H17A H 0.1228 0.9104 -0.3091 0.039 Uiso 1 1 calc R
C18 C 0.2399(4) 0.7337(4) -0.2341(3) 0.0363(9) Uani 1 1 d .
H18A H 0.2128 0.7049 -0.2858 0.044 Uiso 1 1 calc R
C19 C 0.3315(5) 0.6545(4) -0.1464(3) 0.0375(9) Uani 1 1 d .
H19A H 0.3686 0.5712 -0.1382 0.045 Uiso 1 1 calc R
C20 C 0.3709(4) 0.6949(3) -0.0687(3) 0.0285(8) Uani 1 1 d .
H20A H 0.4334 0.6391 -0.0071 0.034 Uiso 1 1 calc R
C21 C 0.4142(3) 0.7270(3) 0.1530(3) 0.0159(6) Uani 1 1 d .
C22 C 0.5543(3) 0.6871(3) 0.1842(3) 0.0189(6) Uani 1 1 d .
H22A H 0.6197 0.7341 0.1371 0.023 Uiso 1 1 calc R
C23 C 0.5988(3) 0.5789(3) 0.2839(3) 0.0219(7) Uani 1 1 d .
H23A H 0.6945 0.5516 0.3044 0.026 Uiso 1 1 calc R
C24 C 0.5035(3) 0.5115(3) 0.3530(3) 0.0226(7) Uani 1 1 d .
H24A H 0.5334 0.4376 0.4212 0.027 Uiso 1 1 calc R
C25 C 0.3631(3) 0.5518(3) 0.3228(3) 0.0221(7) Uani 1 1 d .
H25A H 0.2976 0.5058 0.3711 0.026 Uiso 1 1 calc R
C26 C 0.3184(3) 0.6584(3) 0.2229(3) 0.0190(6) Uani 1 1 d .
H26A H 0.2228 0.6846 0.2021 0.023 Uiso 1 1 calc R
C27 C 0.0129(3) 0.7185(3) 0.4986(3) 0.0282(8) Uani 1 1 d .
H27A H -0.0294 0.7299 0.4257 0.034 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 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
P2 Ni1 P2 180.0 2_675 .
P2 Ni1 P1 96.35(3) 2_675 .
P2 Ni1 P1 83.65(3) . .
P2 Ni1 P1 83.65(3) 2_675 2_675
P2 Ni1 P1 96.35(3) . 2_675
P1 Ni1 P1 180.0 . 2_675
C7 P1 C1 105.95(14) . .
C7 P1 C13 104.30(15) . .
C1 P1 C13 103.01(14) . .
C7 P1 Ni1 114.21(10) . .
C1 P1 Ni1 118.44(11) . .
C13 P1 Ni1 109.50(9) . .
C21 P2 C15 105.35(14) . .
C21 P2 C14 106.26(14) . .
C15 P2 C14 103.24(13) . .
C21 P2 Ni1 107.65(9) . .
C15 P2 Ni1 127.30(11) . .
C14 P2 Ni1 105.43(10) . .
C6 C1 C2 119.5(3) . .
C6 C1 P1 122.2(2) . .
C2 C1 P1 118.3(2) . .
C3 C2 C1 120.0(3) . .
C4 C3 C2 120.2(3) . .
C5 C4 C3 120.1(3) . .
C4 C5 C6 120.5(3) . .
C5 C6 C1 119.7(3) . .
C12 C7 C8 119.2(3) . .
C12 C7 P1 120.8(2) . .
C8 C7 P1 119.8(2) . .
C9 C8 C7 120.4(3) . .
C10 C9 C8 119.7(3) . .
C9 C10 C11 120.5(3) . .
C12 C11 C10 119.8(3) . .
C11 C12 C7 120.3(3) . .
C14 C13 P1 110.8(2) . .
C13 C14 P2 108.02(19) . .
C20 C15 C16 119.9(3) . .
C20 C15 P2 120.7(2) . .
C16 C15 P2 119.3(2) . .
C17 C16 C15 119.3(3) . .
C18 C17 C16 120.2(3) . .
C19 C18 C17 120.4(3) . .
C18 C19 C20 120.5(3) . .
C15 C20 C19 119.6(3) . .
C26 C21 C22 119.6(3) . .
C26 C21 P2 120.9(2) . .
C22 C21 P2 119.5(2) . .
C23 C22 C21 120.4(3) . .
C24 C23 C22 119.8(3) . .
C23 C24 C25 120.0(3) . .
C26 C25 C24 120.5(3) . .
C25 C26 C21 119.7(3) . .
Cl3 C27 Cl1 110.9(2) . .
Cl3 C27 Cl2 108.76(18) . .
Cl1 C27 Cl2 110.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 P2 2.2367(7) 2_675
Ni1 P2 2.2367(7) .
Ni1 P1 2.2447(7) .
Ni1 P1 2.2447(7) 2_675
P1 C7 1.810(3) .
P1 C1 1.812(3) .
P1 C13 1.859(3) .
P2 C21 1.819(3) .
P2 C15 1.820(3) .
P2 C14 1.827(3) .
Cl1 C27 1.762(3) .
Cl2 C27 1.769(4) .
Cl3 C27 1.748(4) .
C1 C6 1.392(4) .
C1 C2 1.399(5) .
C2 C3 1.385(5) .
C3 C4 1.384(5) .
C4 C5 1.377(5) .
C5 C6 1.392(5) .
C7 C12 1.390(4) .
C7 C8 1.396(4) .
C8 C9 1.388(5) .
C9 C10 1.380(5) .
C10 C11 1.388(5) .
C11 C12 1.387(5) .
C13 C14 1.519(4) .
C15 C20 1.390(5) .
C15 C16 1.400(4) .
C16 C17 1.394(5) .
C17 C18 1.385(6) .
C18 C19 1.367(6) .
C19 C20 1.396(5) .
C21 C26 1.393(4) .
C21 C22 1.394(4) .
C22 C23 1.393(5) .
C23 C24 1.380(5) .
C24 C25 1.394(4) .
C25 C26 1.385(5) .
