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#$Date: 2019-11-10 19:25:46 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/59/4515982.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_4515982
loop_
_publ_author_name
'Wellala, Nadeesha P. N.'
'Luebking, John D.'
'Krause, Jeanette A.'
'Guan, Hairong'
_publ_section_title
;
 Roles of Hydrogen Bonding in Proton Transfer to
 κP,κN,κP-N(CH₂CH₂P
  ⁱ  Pr₂)₂-Ligated Nickel Pincer
 Complexes.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              4986
_journal_page_last               5001
_journal_paper_doi               10.1021/acsomega.8b00777
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C22 H42 N P2 Ni, P F6'
_chemical_formula_sum            'C22 H42 F6 N Ni P3'
_chemical_formula_weight         586.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.3608(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5129(11)
_cell_length_b                   14.7798(19)
_cell_length_c                   10.9220(14)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.33
_cell_volume                     1359.6(3)
_computing_cell_refinement       'Bruker SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5.0 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Bruker TRIUMPH curved-graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.359
_diffrn_reflns_theta_min         1.885
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016.2 (Sheldrick, 2016)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.045
_refine_diff_density_max         1.430
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+2.2647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3119
_reflns_number_total             3518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao8b00777_si_002.cif
_cod_data_source_block           '[2H]PF6'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4515982
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.883
_shelx_estimated_absorpt_t_max   0.959
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.28135(4) 0.7500 0.73175(3) 0.01540(12) Uani 1 2 d S T P . .
P1 P 0.30671(7) 0.60223(4) 0.72716(5) 0.01796(14) Uani 1 1 d . . . . .
N1 N 0.3316(3) 0.7500 0.5586(2) 0.0192(5) Uani 1 2 d S T P . .
H1 H 0.429(5) 0.7500 0.563(4) 0.023 Uiso 1 2 d S U P . .
C1 C 0.3399(3) 0.58430(16) 0.5651(2) 0.0228(4) Uani 1 1 d . . . . .
H1A H 0.4547 0.5770 0.5614 0.027 Uiso 1 1 calc R U . . .
H1B H 0.2843 0.5289 0.5313 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2756(3) 0.66638(15) 0.4900(2) 0.0222(4) Uani 1 1 d . . . . .
H2A H 0.3133 0.6657 0.4084 0.027 Uiso 1 1 calc R U . . .
H2B H 0.1581 0.6648 0.4761 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1491(3) 0.52107(16) 0.7491(2) 0.0266(5) Uani 1 1 d . . . . .
H5A H 0.1797 0.4612 0.7170 0.032 Uiso 1 1 calc R U . . .
C6 C -0.0082(3) 0.5491(2) 0.6719(3) 0.0348(6) Uani 1 1 d . . . . .
H6A H 0.0063 0.5547 0.5848 0.052 Uiso 1 1 calc R U . . .
H6B H -0.0424 0.6074 0.7017 0.052 Uiso 1 1 calc R U . . .
H6C H -0.0891 0.5032 0.6798 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1314(4) 0.5083(2) 0.8855(3) 0.0397(7) Uani 1 1 d . . . . .
H7A H 0.2311 0.4851 0.9307 0.060 Uiso 1 1 calc R U . . .
H7B H 0.0457 0.4651 0.8923 0.060 Uiso 1 1 calc R U . . .
H7C H 0.1061 0.5665 0.9208 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4863(3) 0.55771(16) 0.8237(2) 0.0254(5) Uani 1 1 d . . . . .
H8A H 0.4672 0.5609 0.9118 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5203(4) 0.45869(19) 0.7961(3) 0.0406(7) Uani 1 1 d . . . . .
H9A H 0.4316 0.4209 0.8136 0.061 Uiso 1 1 calc R U . . .
H9B H 0.6180 0.4394 0.8482 0.061 Uiso 1 1 calc R U . . .
H9C H 0.5329 0.4524 0.7087 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6295(3) 0.6175(2) 0.8121(3) 0.0397(6) Uani 1 1 d . . . . .
H10A H 0.6073 0.6796 0.8358 0.059 Uiso 1 1 calc R U . . .
H10B H 0.6509 0.6166 0.7263 0.059 Uiso 1 1 calc R U . . .
H10C H 0.7224 0.5945 0.8668 0.059 Uiso 1 1 calc R U . . .
C17 C 0.2178(4) 0.7500 0.8914(3) 0.0190(6) Uani 1 2 d S T P . .
C18 C 0.3233(4) 0.7500 1.0025(3) 0.0233(6) Uani 1 2 d S T P . .
H18A H 0.4343 0.7500 0.9998 0.028 Uiso 1 2 calc R U P . .
C19 C 0.2686(5) 0.7500 1.1172(3) 0.0285(7) Uani 1 2 d S T P . .
H19A H 0.3428 0.7500 1.1912 0.034 Uiso 1 2 calc R U P . .
C20 C 0.1072(5) 0.7500 1.1241(3) 0.0319(8) Uani 1 2 d S T P . .
H20A H 0.0701 0.7500 1.2020 0.038 Uiso 1 2 calc R U P . .
C21 C 0.0006(5) 0.7500 1.0145(4) 0.0300(7) Uani 1 2 d S T P . .
H21A H -0.1103 0.7500 1.0178 0.036 Uiso 1 2 calc R U P . .
C22 C 0.0547(4) 0.7500 0.9004(3) 0.0245(6) Uani 1 2 d S T P . .
H22A H -0.0201 0.7500 0.8269 0.029 Uiso 1 2 calc R U P . .
P3 P 0.75829(11) 0.7500 0.43754(9) 0.0291(2) Uani 1 2 d S T P . .
F1 F 0.9209(7) 0.7500 0.5407(12) 0.056(2) Uani 0.5 2 d S TU P A 1
F2 F 0.8473(11) 0.8361(4) 0.4020(6) 0.090(2) Uani 0.5 1 d D U P A 1
F3 F 0.6546(11) 0.7500 0.3036(7) 0.077(2) Uani 0.5 2 d DS TU P A 1
F4 F 0.6752(7) 0.7922(5) 0.5426(7) 0.115(2) Uani 0.5 1 d D U P A 1
F5 F 0.8662(12) 0.7500 0.5556(13) 0.079(3) Uani 0.5 2 d DS TU P A 2
F6 F 0.8537(9) 0.8077(6) 0.3546(8) 0.099(2) Uani 0.5 1 d D U P A 2
F7 F 0.5829(9) 0.7500 0.3648(7) 0.0645(18) Uani 0.5 2 d DS TU P A 2
F8 F 0.6798(8) 0.8418(4) 0.4709(5) 0.0775(16) Uani 0.5 1 d . U P A 2
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'
F F 0.0171 0.0103 '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'
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
C17 Ni N1 175.85(13) . .
C17 Ni P1 93.615(19) . .
N1 Ni P1 86.739(18) . .
C17 Ni P1 93.615(19) . 4_575
N1 Ni P1 86.739(19) . 4_575
P1 Ni P1 168.05(4) . 4_575
C5 P1 C8 104.60(12) . .
C5 P1 C1 104.26(11) . .
C8 P1 C1 105.42(11) . .
C5 P1 Ni 124.69(9) . .
C8 P1 Ni 114.66(8) . .
C1 P1 Ni 101.15(8) . .
C2 N1 C2 112.4(2) 4_575 .
C2 N1 Ni 112.32(14) 4_575 .
C2 N1 Ni 112.32(14) . .
C2 C1 P1 107.98(15) . .
N1 C2 C1 109.11(19) . .
C7 C5 C6 111.5(2) . .
C7 C5 P1 112.54(18) . .
C6 C5 P1 110.32(18) . .
C10 C8 C9 111.2(2) . .
C10 C8 P1 110.60(17) . .
C9 C8 P1 113.13(19) . .
C18 C17 C22 117.1(3) . .
C18 C17 Ni 124.2(2) . .
C22 C17 Ni 118.7(2) . .
C19 C18 C17 121.4(3) . .
C20 C19 C18 120.6(3) . .
C19 C20 C21 118.7(3) . .
C22 C21 C20 120.7(3) . .
C21 C22 C17 121.5(3) . .
F5 P3 F6 101.4(5) . 4_575
F5 P3 F6 101.4(6) . .
F6 P3 F6 66.5(6) 4_575 .
F2 P3 F2 109.4(7) 4_575 .
F2 P3 F4 142.9(5) 4_575 .
F2 P3 F4 98.3(4) . .
F2 P3 F4 98.3(4) 4_575 4_575
F2 P3 F4 142.9(5) . 4_575
F4 P3 F4 47.1(6) . 4_575
F5 P3 F8 91.6(3) . 4_575
F6 P3 F8 86.4(4) 4_575 4_575
F6 P3 F8 151.7(4) . 4_575
F5 P3 F8 91.6(3) . .
F6 P3 F8 151.7(4) 4_575 .
F6 P3 F8 86.4(4) . .
F8 P3 F8 118.5(6) 4_575 .
F5 P3 F7 149.5(6) . .
F6 P3 F7 104.0(4) 4_575 .
F6 P3 F7 104.0(4) . .
F8 P3 F7 73.5(3) 4_575 .
F8 P3 F7 73.5(3) . .
F2 P3 F3 89.8(3) 4_575 .
F2 P3 F3 89.8(3) . .
F4 P3 F3 115.1(5) . .
F4 P3 F3 115.1(5) 4_575 .
F2 P3 F1 77.3(4) 4_575 .
F2 P3 F1 77.3(4) . .
F4 P3 F1 85.6(5) . .
F4 P3 F1 85.6(5) 4_575 .
F3 P3 F1 157.2(6) . .
F4 F4 P3 66.5(3) 4_575 .
P3 F6 F6 56.8(3) . 4_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni C17 1.900(3) .
Ni N1 1.999(3) .
Ni P1 2.1960(6) .
Ni P1 2.1960(6) 4_575
P1 C5 1.841(2) .
P1 C8 1.847(2) .
P1 C1 1.851(2) .
N1 C2 1.487(3) 4_575
N1 C2 1.487(3) .
C1 C2 1.521(3) .
C5 C7 1.531(4) .
C5 C6 1.532(4) .
C8 C10 1.526(4) .
C8 C9 1.530(4) .
C17 C18 1.401(4) .
C17 C22 1.405(5) .
C18 C19 1.399(5) .
C19 C20 1.387(6) .
C20 C21 1.393(6) .
C21 C22 1.390(5) .
P3 F5 1.471(12) .
P3 F6 1.556(7) 4_575
P3 F6 1.556(7) .
P3 F2 1.559(6) 4_575
P3 F2 1.559(6) .
P3 F4 1.563(6) .
P3 F4 1.563(6) 4_575
P3 F8 1.578(4) 4_575
P3 F8 1.578(4) .
P3 F7 1.586(7) .
P3 F3 1.595(7) .
P3 F1 1.653(9) .
F4 F4 1.249(16) 4_575
F6 F6 1.706(17) 4_575
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 F4 0.82(4) 2.23(4) 3.021(7) 161(2) .
N1 H1 F4 0.82(4) 2.23(4) 3.021(7) 161(2) 4_575
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_4
C5 P1 C1 C2 109.12(17) . .
C8 P1 C1 C2 -141.01(16) . .
Ni P1 C1 C2 -21.31(17) . .
C2 N1 C2 C1 179.10(15) 4_575 .
Ni N1 C2 C1 -53.1(2) . .
P1 C1 C2 N1 46.4(2) . .
C8 P1 C5 C7 55.5(2) . .
C1 P1 C5 C7 166.01(19) . .
Ni P1 C5 C7 -79.2(2) . .
C8 P1 C5 C6 -179.17(18) . .
C1 P1 C5 C6 -68.71(19) . .
Ni P1 C5 C6 46.0(2) . .
C5 P1 C8 C10 178.54(19) . .
C1 P1 C8 C10 68.9(2) . .
Ni P1 C8 C10 -41.4(2) . .
C5 P1 C8 C9 53.1(2) . .
C1 P1 C8 C9 -56.5(2) . .
Ni P1 C8 C9 -166.84(18) . .
P1 Ni C17 C18 85.240(19) . .
P1 Ni C17 C18 -85.239(19) 4_575 .
P1 Ni C17 C22 -94.760(19) . .
P1 Ni C17 C22 94.761(19) 4_575 .
C22 C17 C18 C19 0.000(2) . .
Ni C17 C18 C19 180.000(1) . .
C17 C18 C19 C20 0.000(2) . .
C18 C19 C20 C21 0.000(2) . .
C19 C20 C21 C22 0.000(2) . .
C20 C21 C22 C17 0.000(2) . .
C18 C17 C22 C21 0.000(2) . .
Ni C17 C22 C21 180.000(1) . .
F2 P3 F4 F4 -25.9(6) 4_575 4_575
F2 P3 F4 F4 -164.6(3) . 4_575
F3 P3 F4 F4 101.8(3) . 4_575
F1 P3 F4 F4 -88.1(2) . 4_575
F5 P3 F6 F6 97.6(4) . 4_575
F8 P3 F6 F6 -18.3(6) 4_575 4_575
F8 P3 F6 F6 -171.4(3) . 4_575
F7 P3 F6 F6 -99.4(3) . 4_575
