#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:10:13 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178986 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/09/4120924.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_4120924
loop_
_publ_author_name
'Jessica Wallick'
'Charles G. Riordan'
'Glenn P. A. Yap'
_publ_section_title
;
 C-H Activation by a Diselenido Dinickel(II) Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14972
_journal_page_last               14974
_journal_paper_doi               10.1021/ja407995r
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C28 H62 F12 N10 Ni2 P2 Se2'
_chemical_formula_weight         1104.15
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 106.304(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.986(6)
_cell_length_b                   12.700(6)
_cell_length_c                   14.465(8)
_cell_measurement_reflns_used    940
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.39
_cell_volume                     2113.3(19)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1925
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.082
_diffrn_reflns_theta_min         2.934
_exptl_absorpt_coefficient_mu    2.778
_exptl_absorpt_correction_T_max  0.8510
_exptl_absorpt_correction_T_min  0.5187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       plate
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0442P)²+8.3947P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1864
_reflns_number_total             1925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja407995r_si_001.cif
_cod_data_source_block           char356b
_cod_original_cell_volume        2113.4(19)
_cod_database_code               4120924
#BEGIN Tags that were not found in dictionaries:
_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   0.519
_shelx_estimated_absorpt_t_max   0.851
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Ni Ni -0.14664(5) 0.5000 0.36094(4) 0.01907(18) Uani 1 2 d S T P
Se Se 0.06954(4) 0.5000 0.45532(3) 0.02308(17) Uani 1 2 d S T P
N1 N -0.3312(4) 0.5000 0.3454(3) 0.0268(9) Uani 1 2 d S T P
N2 N -0.1798(3) 0.3310(2) 0.3307(2) 0.0238(6) Uani 1 1 d . . .
N3 N -0.1296(4) 0.5000 0.2184(3) 0.0251(9) Uani 1 2 d S T P
P1 P 0.0000 0.24009(11) 0.0000 0.0290(3) Uani 1 2 d S T P
F1 F 0.1360(3) 0.2417(3) 0.0158(3) 0.0792(11) Uani 1 1 d . . .
F2 F 0.0000 0.1168(4) 0.0000 0.111(3) Uani 1 2 d S T P
F3 F 0.0000 0.3643(3) 0.0000 0.0575(11) Uani 1 2 d S T P
F4 F 0.0167(4) 0.2417(3) 0.1124(2) 0.0864(12) Uani 1 1 d . . .
C1 C -0.3813(3) 0.4043(3) 0.2915(3) 0.0392(10) Uani 1 1 d . . .
H1A H -0.3899 0.4147 0.2220 0.047 Uiso 1 1 calc R U .
H1B H -0.4594 0.3908 0.2997 0.047 Uiso 1 1 calc R U .
C2 C -0.3030(4) 0.3109(4) 0.3282(4) 0.0481(12) Uani 1 1 d . . .
H2A H -0.3066 0.2930 0.3939 0.058 Uiso 1 1 calc R U .
H2B H -0.3320 0.2494 0.2862 0.058 Uiso 1 1 calc R U .
C3 C -0.1589(5) 0.3109(3) 0.2359(3) 0.0432(11) Uani 1 1 d . . .
H3A H -0.2066 0.2501 0.2050 0.052 Uiso 1 1 calc R U .
H3B H -0.0762 0.2919 0.2462 0.052 Uiso 1 1 calc R U .
C4 C -0.1874(4) 0.4045(3) 0.1688(3) 0.0355(9) Uani 1 1 d . . .
H4A H -0.1610 0.3908 0.1110 0.043 Uiso 1 1 calc R U .
H4B H -0.2726 0.4154 0.1478 0.043 Uiso 1 1 calc R U .
C5 C -0.3551(5) 0.5000 0.4405(5) 0.054(2) Uani 1 2 d S T P
H5A H -0.2823 0.5106 0.4913 0.082 Uiso 0.5 1 calc R U P
H5B H -0.3895 0.4324 0.4503 0.082 Uiso 0.5 1 calc R U P
H5C H -0.4094 0.5571 0.4427 0.082 Uiso 0.5 1 calc R U P
C6 C -0.1086(4) 0.2560(3) 0.3998(3) 0.0318(8) Uani 1 1 d . . .
H6A H -0.1295 0.1840 0.3772 0.048 Uiso 1 1 calc R U .
H6B H -0.1226 0.2657 0.4628 0.048 Uiso 1 1 calc R U .
H6C H -0.0262 0.2683 0.4055 0.048 Uiso 1 1 calc R U .
C7 C -0.0066(5) 0.5000 0.2166(4) 0.0486(17) Uani 1 2 d S T P
H7A H -0.0033 0.5009 0.1497 0.073 Uiso 0.5 1 calc R U P
H7B H 0.0322 0.4365 0.2488 0.073 Uiso 0.5 1 calc R U P
H7C H 0.0327 0.5625 0.2503 0.073 Uiso 0.5 1 calc R U P
N4 N 0.3117(6) 0.5000 0.2801(5) 0.0626(17) Uani 1 2 d S T P
C8 C 0.2942(6) 0.5000 0.1991(5) 0.0454(15) Uani 1 2 d S T P
C9 C 0.2758(7) 0.5000 0.0949(5) 0.061(2) Uani 1 2 d S T P
H9A H 0.3420 0.5340 0.0797 0.091 Uiso 0.5 1 calc R U P
H9B H 0.2044 0.5387 0.0637 0.091 Uiso 0.5 1 calc R U P
H9C H 0.2688 0.4273 0.0712 0.091 Uiso 0.5 1 calc R U P
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'
Se Se -0.0929 2.2259 '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
N3 Ni N1 105.86(17) . .
N3 Ni N2 82.46(8) . .
N1 Ni N2 81.78(8) . .
N3 Ni N2 82.46(8) . 6_565
N1 Ni N2 81.78(8) . 6_565
N2 Ni N2 153.70(15) . 6_565
N3 Ni Se 154.42(12) . 5_566
N1 Ni Se 99.73(12) . 5_566
N2 Ni Se 101.46(8) . 5_566
N2 Ni Se 101.46(8) 6_565 5_566
N3 Ni Se 99.10(12) . .
N1 Ni Se 155.05(12) . .
N2 Ni Se 101.79(8) . .
N2 Ni Se 101.79(8) 6_565 .
Se Ni Se 55.32(2) 5_566 .
Se Se Ni 62.56(4) 5_566 5_566
Se Se Ni 62.12(4) 5_566 .
Ni Se Ni 124.68(2) 5_566 .
C1 N1 C1 110.7(4) . 6_565
C1 N1 C5 109.5(3) . .
C1 N1 C5 109.5(3) 6_565 .
C1 N1 Ni 107.9(2) . .
C1 N1 Ni 107.9(2) 6_565 .
C5 N1 Ni 111.3(3) . .
C6 N2 C3 107.5(3) . .
C6 N2 C2 106.8(3) . .
C3 N2 C2 111.8(4) . .
C6 N2 Ni 117.3(2) . .
C3 N2 Ni 106.4(2) . .
C2 N2 Ni 107.1(2) . .
C4 N3 C4 110.2(4) 6_565 .
C4 N3 C7 108.9(3) 6_565 .
C4 N3 C7 108.9(3) . .
C4 N3 Ni 108.1(2) 6_565 .
C4 N3 Ni 108.1(2) . .
C7 N3 Ni 112.6(3) . .
F2 P1 F3 180.0 . .
F2 P1 F4 90.74(17) . .
F3 P1 F4 89.26(17) . .
F2 P1 F4 90.74(17) . 2
F3 P1 F4 89.26(17) . 2
F4 P1 F4 178.5(3) . 2
F2 P1 F1 90.75(15) . .
F3 P1 F1 89.25(15) . .
F4 P1 F1 91.3(2) . .
F4 P1 F1 88.6(2) 2 .
F2 P1 F1 90.75(15) . 2
F3 P1 F1 89.25(15) . 2
F4 P1 F1 88.6(2) . 2
F4 P1 F1 91.3(2) 2 2
F1 P1 F1 178.5(3) . 2
N1 C1 C2 109.8(4) . .
N2 C2 C1 112.8(3) . .
N2 C3 C4 113.1(3) . .
N3 C4 C3 110.0(3) . .
N4 C8 C9 178.0(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni N3 2.128(4) .
Ni N1 2.160(4) .
Ni N2 2.204(3) .
Ni N2 2.204(3) 6_565
Ni Se 2.5571(15) 5_566
Ni Se 2.5675(13) .
Se Se 2.3791(13) 5_566
Se Ni 2.5571(16) 5_566
N1 C1 1.478(5) .
N1 C1 1.478(5) 6_565
N1 C5 1.481(7) .
N2 C6 1.468(5) .
N2 C3 1.483(5) .
N2 C2 1.489(5) .
N3 C4 1.479(4) 6_565
N3 C4 1.479(4) .
N3 C7 1.482(7) .
P1 F2 1.565(5) .
P1 F3 1.577(4) .
P1 F4 1.581(3) .
P1 F4 1.581(3) 2
P1 F1 1.581(3) .
P1 F1 1.581(3) 2
C1 C2 1.514(6) .
C3 C4 1.511(6) .
N4 C8 1.132(9) .
C8 C9 1.461(10) .
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
C1 N1 C1 C2 160.6(3) 6_565
C5 N1 C1 C2 -78.6(5) .
Ni N1 C1 C2 42.7(4) .
C6 N2 C2 C1 158.3(4) .
C3 N2 C2 C1 -84.4(5) .
Ni N2 C2 C1 31.9(5) .
N1 C1 C2 N2 -51.5(5) .
C6 N2 C3 C4 -157.9(4) .
C2 N2 C3 C4 85.2(5) .
Ni N2 C3 C4 -31.4(4) .
C4 N3 C4 C3 -160.0(3) 6_565
C7 N3 C4 C3 80.5(4) .
Ni N3 C4 C3 -42.1(4) .
N2 C3 C4 N3 50.9(5) .
