#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105689.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_7105689
loop_
_publ_author_name
'Jenny Yang'
'Shentan Chen'
'William Dougherty'
'Scott Kassel'
'Morris Bullock'
'Daniel DuBois'
'Simone Raugei'
'Roger Rousseau'
'Michel Dupuis'
'Rakowski DuBois'
_publ_section_title
;
 Hydrogen Oxidation Catalysis by a Nickel Diphosphine Complex with Pendant
 t-Butyl Amines
;
_journal_name_full               Chem.Commun.
_journal_page_first              8618
_journal_paper_doi               10.1039/c0cc03246h
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C26.57 H53 B F4 N2.71 Ni0.5 O0.29 P2'
_chemical_formula_weight         593.25
_chemical_name_systematic
;
?
;
_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                 101.782(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.9513(10)
_cell_length_b                   13.9953(6)
_cell_length_c                   22.0669(10)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      2.44
_cell_volume                     6334.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            40666
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.27
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.9286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2550
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.990
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         12025
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0472
_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)+(0.0634P)²+3.5411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                8509
_reflns_number_total             12025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03246H.TXT
_cod_data_source_block           pnl086
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C26.57 H53 B F4 N2.71 Ni0.50 O0.29 P2'
_cod_database_code               7105689
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.0000 0.112219(19) 0.7500 0.01240(7) Uani 1 2 d S . .
B1 B 0.94009(10) 0.25598(15) 0.45170(10) 0.0237(4) Uani 1 1 d . . .
F1 F 0.94225(7) 0.16547(9) 0.47797(6) 0.0408(3) Uani 1 1 d . . .
F2 F 0.93036(6) 0.24684(9) 0.38799(5) 0.0347(3) Uani 1 1 d . . .
F3 F 0.99899(6) 0.30157(10) 0.47444(6) 0.0413(3) Uani 1 1 d . . .
F4 F 0.89008(7) 0.30732(12) 0.46834(8) 0.0567(4) Uani 1 1 d . . .
N1 N 0.92174(6) 0.07660(9) 0.86139(6) 0.0158(3) Uani 1 1 d . . .
N2 N 0.87027(6) 0.14715(9) 0.64221(7) 0.0167(3) Uani 1 1 d . . .
P1 P 0.995049(19) 0.21301(3) 0.671013(19) 0.01407(8) Uani 1 1 d . . .
P2 P 1.031657(18) 0.01098(3) 0.828236(19) 0.01294(8) Uani 1 1 d . . .
C1 C 1.09216(8) 0.34848(12) 0.71702(9) 0.0226(3) Uani 1 1 d . . .
H1A H 1.0968 0.3135 0.7567 0.027 Uiso 1 1 calc R . .
H1B H 1.1229 0.3202 0.6934 0.027 Uiso 1 1 calc R . .
C2 C 1.10875(10) 0.45417(14) 0.72985(10) 0.0319(4) Uani 1 1 d . . .
H2A H 1.0808 0.4806 0.7569 0.038 Uiso 1 1 calc R . .
H2B H 1.1548 0.4601 0.7518 0.038 Uiso 1 1 calc R . .
C3 C 1.09841(10) 0.51114(14) 0.66981(11) 0.0352(5) Uani 1 1 d . . .
H3A H 1.1061 0.5797 0.6796 0.042 Uiso 1 1 calc R . .
H3B H 1.1305 0.4902 0.6453 0.042 Uiso 1 1 calc R . .
C4 C 1.02994(10) 0.49824(13) 0.63147(11) 0.0344(5) Uani 1 1 d . . .
H4A H 1.0261 0.5331 0.5918 0.041 Uiso 1 1 calc R . .
H4B H 0.9980 0.5260 0.6540 0.041 Uiso 1 1 calc R . .
C5 C 1.01386(9) 0.39251(12) 0.61812(9) 0.0249(4) Uani 1 1 d . . .
H5A H 1.0434 0.3654 0.5928 0.030 Uiso 1 1 calc R . .
H5B H 0.9685 0.3859 0.5946 0.030 Uiso 1 1 calc R . .
C6 C 1.02213(8) 0.33831(11) 0.67992(8) 0.0185(3) Uani 1 1 d . . .
H6A H 0.9933 0.3709 0.7045 0.022 Uiso 1 1 calc R . .
C7 C 1.04514(8) 0.16600(11) 0.61715(8) 0.0175(3) Uani 1 1 d . . .
H7A H 1.0167 0.1554 0.5760 0.021 Uiso 1 1 calc R . .
H7B H 1.0781 0.2144 0.6122 0.021 Uiso 1 1 calc R . .
C8 C 0.86037(8) 0.06122(13) 0.88555(9) 0.0219(3) Uani 1 1 d . . .
C9 C 0.82905(9) -0.03303(14) 0.85992(11) 0.0308(4) Uani 1 1 d . . .
H9A H 0.8250 -0.0343 0.8149 0.046 Uiso 1 1 calc R . .
H9B H 0.7857 -0.0387 0.8699 0.046 Uiso 1 1 calc R . .
H9C H 0.8564 -0.0865 0.8785 0.046 Uiso 1 1 calc R . .
C10 C 0.87320(10) 0.05989(15) 0.95638(9) 0.0307(4) Uani 1 1 d . . .
H10A H 0.9030 0.0074 0.9719 0.046 Uiso 1 1 calc R . .
H10B H 0.8319 0.0508 0.9700 0.046 Uiso 1 1 calc R . .
H10C H 0.8929 0.1207 0.9725 0.046 Uiso 1 1 calc R . .
C11 C 0.81219(9) 0.14087(15) 0.86023(11) 0.0315(4) Uani 1 1 d . . .
H11A H 0.8094 0.1473 0.8155 0.047 Uiso 1 1 calc R . .
H11B H 0.8273 0.2013 0.8807 0.047 Uiso 1 1 calc R . .
H11C H 0.7691 0.1251 0.8682 0.047 Uiso 1 1 calc R . .
C12 C 0.96909(7) -0.00097(11) 0.87556(8) 0.0161(3) Uani 1 1 d . . .
H12A H 0.9466 -0.0632 0.8669 0.019 Uiso 1 1 calc R . .
H12B H 0.9900 0.0009 0.9200 0.019 Uiso 1 1 calc R . .
C13 C 1.10600(8) -0.12243(12) 0.77759(8) 0.0188(3) Uani 1 1 d . . .
H13A H 1.1474 -0.0925 0.7988 0.023 Uiso 1 1 calc R . .
H13B H 1.0904 -0.0882 0.7381 0.023 Uiso 1 1 calc R . .
C14 C 1.11801(9) -0.22776(13) 0.76441(9) 0.0249(4) Uani 1 1 d . . .
H14A H 1.0776 -0.2561 0.7399 0.030 Uiso 1 1 calc R . .
H14B H 1.1524 -0.2325 0.7397 0.030 Uiso 1 1 calc R . .
C15 C 1.13893(9) -0.28303(13) 0.82458(9) 0.0286(4) Uani 1 1 d . . .
H15A H 1.1820 -0.2596 0.8466 0.034 Uiso 1 1 calc R . .
H15B H 1.1434 -0.3515 0.8151 0.034 Uiso 1 1 calc R . .
C16 C 1.08965(10) -0.27200(12) 0.86645(9) 0.0273(4) Uani 1 1 d . . .
H16A H 1.1059 -0.3060 0.9059 0.033 Uiso 1 1 calc R . .
H16B H 1.0478 -0.3017 0.8462 0.033 Uiso 1 1 calc R . .
C17 C 1.07809(8) -0.16712(12) 0.87997(8) 0.0197(3) Uani 1 1 d . . .
H17A H 1.1189 -0.1382 0.9033 0.024 Uiso 1 1 calc R . .
H17B H 1.0445 -0.1620 0.9055 0.024 Uiso 1 1 calc R . .
C18 C 1.05529(7) -0.11386(10) 0.81829(7) 0.0149(3) Uani 1 1 d . . .
H18A H 1.0152 -0.1475 0.7959 0.018 Uiso 1 1 calc R . .
C19 C 1.10613(7) 0.05825(11) 0.87996(8) 0.0175(3) Uani 1 1 d . . .
H19A H 1.0967 0.0693 0.9216 0.021 Uiso 1 1 calc R . .
H19B H 1.1410 0.0095 0.8841 0.021 Uiso 1 1 calc R . .
C20 C 0.79778(8) 0.16032(12) 0.61792(9) 0.0244(4) Uani 1 1 d . . .
C21 C 0.76228(9) 0.08711(16) 0.65072(12) 0.0355(5) Uani 1 1 d . . .
H21A H 0.7778 0.0925 0.6956 0.053 Uiso 1 1 calc R . .
H21B H 0.7711 0.0226 0.6372 0.053 Uiso 1 1 calc R . .
H21C H 0.7153 0.0994 0.6403 0.053 Uiso 1 1 calc R . .
C22 C 0.77848(9) 0.14652(17) 0.54751(10) 0.0359(5) Uani 1 1 d . . .
H22A H 0.8054 0.1879 0.5271 0.054 Uiso 1 1 calc R . .
H22B H 0.7324 0.1632 0.5333 0.054 Uiso 1 1 calc R . .
H22C H 0.7853 0.0796 0.5372 0.054 Uiso 1 1 calc R . .
C23 C 0.77730(10) 0.25888(15) 0.63524(14) 0.0442(6) Uani 1 1 d . . .
H23A H 0.7931 0.2694 0.6797 0.066 Uiso 1 1 calc R . .
H23B H 0.7296 0.2636 0.6254 0.066 Uiso 1 1 calc R . .
H23C H 0.7959 0.3073 0.6118 0.066 Uiso 1 1 calc R . .
C24 C 0.91061(7) 0.22556(11) 0.62709(8) 0.0178(3) Uani 1 1 d . . .
H24A H 0.8924 0.2874 0.6374 0.021 Uiso 1 1 calc R . .
H24B H 0.9103 0.2250 0.5822 0.021 Uiso 1 1 calc R . .
N3 N 1.16333(17) -0.5122(2) 0.90254(17) 0.0535(9) Uani 0.725(3) 1 d P A 1
C25 C 1.11785(18) -0.4721(3) 0.99993(15) 0.0434(8) Uani 0.725(3) 1 d P A 1
H25A H 1.1513 -0.4393 1.0304 0.065 Uiso 0.725(3) 1 calc PR A 1
H25B H 1.1047 -0.5308 1.0182 0.065 Uiso 0.725(3) 1 calc PR A 1
H25C H 1.0799 -0.4302 0.9879 0.065 Uiso 0.725(3) 1 calc PR A 1
C26 C 1.14333(16) -0.4950(2) 0.94709(17) 0.0347(7) Uani 0.725(3) 1 d P A 1
C27 C 1.2841(5) -0.1935(7) 0.9751(5) 0.0505(12) Uani 0.275(3) 1 d PD A -2
H27A H 1.2929 -0.1420 1.0058 0.076 Uiso 0.275(3) 1 calc PR A -2
H27B H 1.2601 -0.1679 0.9357 0.076 Uiso 0.275(3) 1 calc PR A -2
H27C H 1.3255 -0.2208 0.9692 0.076 Uiso 0.275(3) 1 calc PR A -2
C28 C 1.2428(6) -0.2727(6) 0.9984(6) 0.0505(12) Uani 0.275(3) 1 d PD A -2
H28A H 1.2054 -0.2354 1.0069 0.061 Uiso 0.275(3) 1 calc PR A -2
H28B H 1.2695 -0.2872 1.0398 0.061 Uiso 0.275(3) 1 calc PR A -2
C29 C 1.1596(5) -0.4525(7) 0.9910(5) 0.0505(12) Uani 0.275(3) 1 d PD A -2
H29A H 1.1157 -0.4246 0.9884 0.061 Uiso 0.275(3) 1 calc PR A -2
H29B H 1.1744 -0.4820 1.0323 0.061 Uiso 0.275(3) 1 calc PR A -2
C30 C 1.1603(6) -0.5260(9) 0.9380(6) 0.0505(12) Uani 0.275(3) 1 d PD A -2
H30A H 1.1301 -0.5783 0.9413 0.076 Uiso 0.275(3) 1 calc PR A -2
H30B H 1.2044 -0.5515 0.9415 0.076 Uiso 0.275(3) 1 calc PR A -2
H30C H 1.1467 -0.4942 0.8979 0.076 Uiso 0.275(3) 1 calc PR A -2
O1 O 1.2084(3) -0.3776(4) 0.9778(3) 0.0505(12) Uani 0.275(3) 1 d PD 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'
O O 0.0106 0.0060 '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'
B B 0.0013 0.0007 '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'
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
P2 Ni1 P2 100.99(2) . 2_756 ?
P2 Ni1 P1 165.477(14) . . ?
P2 Ni1 P1 80.643(15) 2_756 . ?
P2 Ni1 P1 80.642(15) . 2_756 ?
P2 Ni1 P1 165.475(14) 2_756 2_756 ?
P1 Ni1 P1 101.45(2) . 2_756 ?
F4 B1 F2 110.83(17) . . ?
F4 B1 F1 108.99(17) . . ?
F2 B1 F1 108.95(16) . . ?
F4 B1 F3 109.36(17) . . ?
F2 B1 F3 110.18(16) . . ?
F1 B1 F3 108.49(16) . . ?
C12 N1 C7 108.06(12) . 2_756 ?
C12 N1 C8 114.21(12) . . ?
C7 N1 C8 113.03(13) 2_756 . ?
C19 N2 C24 108.15(12) 2_756 . ?
C19 N2 C20 111.64(13) 2_756 . ?
C24 N2 C20 114.31(12) . . ?
C6 P1 C24 101.95(7) . . ?
C6 P1 C7 101.74(7) . . ?
C24 P1 C7 107.69(8) . . ?
C6 P1 Ni1 123.73(6) . . ?
C24 P1 Ni1 110.97(5) . . ?
C7 P1 Ni1 109.51(5) . . ?
C18 P2 C12 102.77(7) . . ?
C18 P2 C19 101.46(7) . . ?
C12 P2 C19 106.84(8) . . ?
C18 P2 Ni1 123.78(5) . . ?
C12 P2 Ni1 111.30(5) . . ?
C19 P2 Ni1 109.25(5) . . ?
C2 C1 C6 110.14(15) . . ?
C3 C2 C1 110.96(16) . . ?
C4 C3 C2 111.86(16) . . ?
C3 C4 C5 111.53(16) . . ?
C4 C5 C6 108.97(16) . . ?
C1 C6 C5 110.45(14) . . ?
C1 C6 P1 112.68(11) . . ?
C5 C6 P1 113.47(12) . . ?
N1 C7 P1 112.85(11) 2_756 . ?
N1 C8 C10 112.26(14) . . ?
N1 C8 C11 108.30(14) . . ?
C10 C8 C11 110.29(16) . . ?
N1 C8 C9 108.99(14) . . ?
C10 C8 C9 109.86(16) . . ?
C11 C8 C9 106.98(16) . . ?
N1 C12 P2 109.99(11) . . ?
C18 C13 C14 110.33(14) . . ?
C15 C14 C13 110.63(15) . . ?
C14 C15 C16 111.51(15) . . ?
C15 C16 C17 111.67(15) . . ?
C16 C17 C18 109.00(14) . . ?
C13 C18 C17 110.72(13) . . ?
C13 C18 P2 112.36(11) . . ?
C17 C18 P2 113.35(11) . . ?
N2 C19 P2 113.41(11) 2_756 . ?
N2 C20 C23 109.65(15) . . ?
N2 C20 C21 107.45(14) . . ?
C23 C20 C21 107.44(17) . . ?
N2 C20 C22 112.36(15) . . ?
C23 C20 C22 109.86(18) . . ?
C21 C20 C22 109.94(17) . . ?
N2 C24 P1 110.20(11) . . ?
N3 C26 C25 178.2(4) . . ?
C27 C28 O1 141.2(9) . . ?
O1 C29 C30 101.5(8) . . ?
C29 O1 C28 145.3(7) . . ?
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 P2 2.2272(4) . ?
Ni1 P2 2.2272(4) 2_756 ?
Ni1 P1 2.2281(4) . ?
Ni1 P1 2.2282(4) 2_756 ?
B1 F4 1.381(2) . ?
B1 F2 1.385(2) . ?
B1 F1 1.390(2) . ?
B1 F3 1.389(2) . ?
N1 C12 1.4608(19) . ?
N1 C7 1.462(2) 2_756 ?
N1 C8 1.505(2) . ?
N2 C19 1.460(2) 2_756 ?
N2 C24 1.465(2) . ?
N2 C20 1.515(2) . ?
P1 C6 1.8413(16) . ?
P1 C24 1.8439(16) . ?
P1 C7 1.8591(16) . ?
P2 C18 1.8413(15) . ?
P2 C12 1.8428(16) . ?
P2 C19 1.8568(16) . ?
C1 C2 1.533(3) . ?
C1 C6 1.534(2) . ?
C2 C3 1.523(3) . ?
C3 C4 1.520(3) . ?
C4 C5 1.533(3) . ?
C5 C6 1.539(2) . ?
C7 N1 1.462(2) 2_756 ?
C8 C10 1.531(3) . ?
C8 C11 1.531(2) . ?
C8 C9 1.529(3) . ?
C13 C18 1.529(2) . ?
C13 C14 1.533(2) . ?
C14 C15 1.522(3) . ?
C15 C16 1.527(3) . ?
C16 C17 1.527(2) . ?
C17 C18 1.540(2) . ?
C19 N2 1.460(2) 2_756 ?
C20 C23 1.517(3) . ?
C20 C21 1.532(3) . ?
C20 C22 1.536(3) . ?
N3 C26 1.170(5) . ?
C25 C26 1.415(5) . ?
C27 C28 1.557(14) . ?
C28 O1 1.657(9) . ?
C29 O1 1.534(11) . ?
C29 C30 1.560(13) . ?
