#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/72/7117222.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_7117222
loop_
_publ_author_name
'Wenfeng Lo'
'Chunhua Hu'
'Tyler Berenson'
'Nathaniel Tracer'
'Daniel Shlian'
'Michael Khaloo'
'Avraham Benhaim'
'Jianfeng Jiang'
_publ_section_title
;
 Oxidation of carbon monoxide in basic solution catalyzed by nickel cyano
 carbonyls under ambient conditions and the prototype of a CO-powered
 alkaline fuel cell
;
_journal_name_full               Chem.Commun.
_journal_page_first              9432
_journal_paper_doi               10.1039/C5cc01872B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C20 H40 N4 Ni O2'
_chemical_formula_weight         427.27
_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
_audit_update_record
;
2015-03-05 deposited with the CCDC.
2015-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.009(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.857(3)
_cell_length_b                   10.303(2)
_cell_length_c                   15.562(3)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      2.65
_cell_volume                     2352.7(8)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13307
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  0.9203
_exptl_absorpt_correction_T_min  0.8230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.9971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                1973
_reflns_number_total             2418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01872b2.cif
_cod_data_source_block           14yuj35
_cod_original_cell_volume        2352.6(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7117222
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 0.5000 0.17157(3) 0.2500 0.02723(13) Uani 1 2 d S . .
O1 O 0.37227(13) 0.00159(19) 0.14253(12) 0.0599(5) Uani 1 1 d . . .
N1 N 0.41137(12) 0.35187(17) 0.37376(12) 0.0354(4) Uani 1 1 d . . .
C1 C 0.44405(13) 0.28692(19) 0.32628(13) 0.0280(4) Uani 1 1 d . . .
C2 C 0.42018(14) 0.0737(2) 0.18406(14) 0.0339(5) Uani 1 1 d . . .
N2 N 0.30761(11) 0.44445(15) 0.61680(10) 0.0261(4) Uani 1 1 d . . .
C3 C 0.36223(15) 0.33966(19) 0.58013(14) 0.0333(5) Uani 1 1 d . . .
H3A H 0.3357 0.2543 0.5913 0.040 Uiso 1 1 calc R . .
H3B H 0.3552 0.3511 0.5163 0.040 Uiso 1 1 calc R . .
C4 C 0.46266(16) 0.3367(2) 0.61586(18) 0.0493(6) Uani 1 1 d . . .
H4A H 0.4926 0.2702 0.5852 0.074 Uiso 1 1 calc R . .
H4B H 0.4710 0.3161 0.6781 0.074 Uiso 1 1 calc R . .
H4C H 0.4896 0.4217 0.6075 0.074 Uiso 1 1 calc R . .
C5 C 0.34217(15) 0.57838(19) 0.59713(15) 0.0356(5) Uani 1 1 d . . .
H5A H 0.3077 0.6442 0.6250 0.043 Uiso 1 1 calc R . .
H5B H 0.4070 0.5854 0.6239 0.043 Uiso 1 1 calc R . .
C6 C 0.33439(17) 0.6100(2) 0.50183(16) 0.0444(6) Uani 1 1 d . . .
H6A H 0.3643 0.6933 0.4948 0.067 Uiso 1 1 calc R . .
H6B H 0.2699 0.6157 0.4762 0.067 Uiso 1 1 calc R . .
H6C H 0.3639 0.5416 0.4724 0.067 Uiso 1 1 calc R . .
C7 C 0.31775(15) 0.4362(2) 0.71526(13) 0.0334(5) Uani 1 1 d . . .
H7A H 0.3812 0.4592 0.7400 0.040 Uiso 1 1 calc R . .
H7B H 0.2773 0.5019 0.7357 0.040 Uiso 1 1 calc R . .
C8 C 0.29608(16) 0.3057(2) 0.75082(14) 0.0400(5) Uani 1 1 d . . .
H8A H 0.3031 0.3102 0.8144 0.060 Uiso 1 1 calc R . .
H8B H 0.3378 0.2403 0.7338 0.060 Uiso 1 1 calc R . .
H8C H 0.2332 0.2818 0.7273 0.060 Uiso 1 1 calc R . .
C9 C 0.20962(13) 0.4246(2) 0.57455(13) 0.0320(5) Uani 1 1 d . . .
H9A H 0.2074 0.4250 0.5106 0.038 Uiso 1 1 calc R . .
H9B H 0.1899 0.3374 0.5910 0.038 Uiso 1 1 calc R . .
C10 C 0.14186(15) 0.5229(2) 0.59717(16) 0.0429(6) Uani 1 1 d . . .
H10A H 0.0809 0.5009 0.5669 0.064 Uiso 1 1 calc R . .
H10B H 0.1589 0.6095 0.5792 0.064 Uiso 1 1 calc R . .
H10C H 0.1418 0.5221 0.6601 0.064 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 0.0033 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'
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
C2 Ni1 C2 110.08(14) 2_655 .
C2 Ni1 C1 107.82(9) 2_655 .
C2 Ni1 C1 112.99(9) . .
C2 Ni1 C1 112.99(9) 2_655 2_655
C2 Ni1 C1 107.82(9) . 2_655
C1 Ni1 C1 105.12(11) . 2_655
N1 C1 Ni1 177.55(18) . .
O1 C2 Ni1 174.7(2) . .
C9 N2 C3 105.98(15) . .
C9 N2 C7 111.55(15) . .
C3 N2 C7 111.45(15) . .
C9 N2 C5 111.56(15) . .
C3 N2 C5 110.69(15) . .
C7 N2 C5 105.72(15) . .
C4 C3 N2 115.66(17) . .
C4 C3 H3A 108.4 . .
N2 C3 H3A 108.4 . .
C4 C3 H3B 108.4 . .
N2 C3 H3B 108.4 . .
H3A C3 H3B 107.4 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 C5 N2 114.75(17) . .
C6 C5 H5A 108.6 . .
N2 C5 H5A 108.6 . .
C6 C5 H5B 108.6 . .
N2 C5 H5B 108.6 . .
H5A C5 H5B 107.6 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 N2 115.30(16) . .
C8 C7 H7A 108.5 . .
N2 C7 H7A 108.5 . .
C8 C7 H7B 108.5 . .
N2 C7 H7B 108.5 . .
H7A C7 H7B 107.5 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 N2 116.06(17) . .
C10 C9 H9A 108.3 . .
N2 C9 H9A 108.3 . .
C10 C9 H9B 108.3 . .
N2 C9 H9B 108.3 . .
H9A C9 H9B 107.4 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C2 1.759(2) 2_655
Ni1 C2 1.759(2) .
Ni1 C1 1.955(2) .
Ni1 C1 1.955(2) 2_655
O1 C2 1.154(3) .
N1 C1 1.158(3) .
N2 C9 1.515(2) .
N2 C3 1.515(2) .
N2 C7 1.518(2) .
N2 C5 1.520(2) .
C3 C4 1.509(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.505(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.507(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.508(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
