#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:12:14 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237422 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/46/1554615.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_1554615
loop_
_publ_author_name
'Dubrawski, Zachary'
'Heidebrecht, Joshua'
'Puerta Lombardi, Braulio M.'
'Hyla, Alexander S.'
'Willkomm, Janina'
'Radford, Chase L.'
'Lin, Jian-Bin'
'Welch, Gregory C.'
'Ponnurangam, Sathish'
'Roesler, Roland'
'Prokopchuk, Demyan E.'
'Piers, Warren E.'
_publ_section_title
;
 Ligand-centered electrochemical processes enable CO2 reduction with a
 nickel bis(triazapentadienyl) complex
;
_journal_issue                   5
_journal_name_full               'Sustainable Energy & Fuels'
_journal_page_first              1172
_journal_paper_doi               10.1039/C8SE00623G
_journal_volume                  3
_journal_year                    2019
_chemical_formula_moiety         'C24 H20 N10 Ni'
_chemical_formula_sum            'C24 H20 N10 Ni'
_chemical_formula_weight         507.21
_chemical_name_common            Ni(TAPPy)2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-14 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.096(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7492(13)
_cell_length_b                   16.392(2)
_cell_length_c                   8.8505(14)
_cell_measurement_reflns_used    1314
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      2.95
_cell_volume                     1103.2(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14166
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         3.436
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.916
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0689 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.8682.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF;Hexanes'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0394
_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)+(0.0253P)²+0.7669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1542
_reflns_number_total             2158
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8se00623g2.cif
_cod_data_source_block           180727zack_0m_a
_cod_database_code               1554615
_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_max   0.914
_shelx_estimated_absorpt_t_min   0.838
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1), N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ni1 Ni 0.5000 0.5000 1.0000 0.02058(16) Uani 1 2 d S T P
N1 N 0.5923(3) 0.40962(13) 0.9231(3) 0.0235(6) Uani 1 1 d . . .
H1 H 0.7068 0.3955 0.9409 0.028 Uiso 1 1 d R . .
N2 N 0.3472(3) 0.35748(14) 0.7475(3) 0.0253(6) Uani 1 1 d . . .
N3 N 0.2876(3) 0.47879(13) 0.8724(3) 0.0247(6) Uani 1 1 d . . .
H3 H 0.1932 0.5081 0.8608 0.030 Uiso 1 1 d R . .
N4 N 0.7935(3) 0.29008(15) 0.8419(3) 0.0292(6) Uani 1 1 d . . .
N5 N -0.0489(3) 0.47330(14) 0.7184(3) 0.0314(6) Uani 1 1 d . . .
C1 C 0.5149(4) 0.35666(16) 0.8216(3) 0.0230(7) Uani 1 1 d . . .
C2 C 0.2439(4) 0.41925(17) 0.7742(3) 0.0234(7) Uani 1 1 d . . .
C3 C 0.8955(4) 0.2319(2) 0.8016(4) 0.0375(8) Uani 1 1 d . . .
H3A H 1.0173 0.2326 0.8461 0.045 Uiso 1 1 calc R . .
C4 C 0.8339(5) 0.17075(19) 0.6989(4) 0.0381(9) Uani 1 1 d . . .
H4 H 0.9122 0.1312 0.6717 0.046 Uiso 1 1 calc R . .
C5 C 0.6577(5) 0.16780(18) 0.6362(4) 0.0370(8) Uani 1 1 d . . .
H5 H 0.6112 0.1257 0.5664 0.044 Uiso 1 1 calc R . .
C6 C 0.5497(4) 0.22755(17) 0.6770(3) 0.0302(7) Uani 1 1 d . . .
H6 H 0.4270 0.2272 0.6360 0.036 Uiso 1 1 calc R . .
C7 C 0.6229(4) 0.28783(17) 0.7784(3) 0.0232(7) Uani 1 1 d . . .
C8 C 0.0619(4) 0.41857(17) 0.6798(3) 0.0247(7) Uani 1 1 d . . .
C9 C 0.0154(4) 0.36501(19) 0.5584(4) 0.0317(8) Uani 1 1 d . . .
H9 H 0.0979 0.3267 0.5343 0.038 Uiso 1 1 calc R . .
C10 C -0.1534(4) 0.3682(2) 0.4729(4) 0.0382(8) Uani 1 1 d . . .
H10 H -0.1889 0.3324 0.3882 0.046 Uiso 1 1 calc R . .
C11 C -0.2686(4) 0.4238(2) 0.5122(4) 0.0372(8) Uani 1 1 d . . .
H11 H -0.3858 0.4271 0.4558 0.045 Uiso 1 1 calc R . .
C12 C -0.2113(4) 0.47487(19) 0.6349(4) 0.0364(8) Uani 1 1 d . . .
H12 H -0.2921 0.5134 0.6616 0.044 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'
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
N1 Ni1 N1 180.0 . 3_667
N1 Ni1 N3 90.81(10) 3_667 .
N1 Ni1 N3 90.81(10) . 3_667
N1 Ni1 N3 89.19(10) 3_667 3_667
N1 Ni1 N3 89.19(10) . .
N3 Ni1 N3 180.00(13) 3_667 .
Ni1 N1 H1 125.8 . .
C1 N1 Ni1 129.1(2) . .
C1 N1 H1 104.8 . .
C1 N2 C2 118.6(2) . .
Ni1 N3 H3 127.1 . .
C2 N3 Ni1 129.5(2) . .
C2 N3 H3 103.4 . .
C3 N4 C7 117.3(3) . .
C8 N5 C12 117.3(3) . .
N1 C1 N2 127.1(3) . .
N1 C1 C7 118.0(3) . .
N2 C1 C7 114.8(2) . .
N2 C2 C8 115.3(2) . .
N3 C2 N2 126.5(3) . .
N3 C2 C8 118.2(3) . .
N4 C3 H3A 118.3 . .
N4 C3 C4 123.4(3) . .
C4 C3 H3A 118.3 . .
C3 C4 H4 120.5 . .
C5 C4 C3 119.0(3) . .
C5 C4 H4 120.5 . .
C4 C5 H5 120.8 . .
C4 C5 C6 118.4(3) . .
C6 C5 H5 120.8 . .
C5 C6 H6 120.5 . .
C5 C6 C7 118.9(3) . .
C7 C6 H6 120.5 . .
N4 C7 C1 115.4(3) . .
N4 C7 C6 122.9(3) . .
C6 C7 C1 121.7(3) . .
N5 C8 C2 116.0(3) . .
N5 C8 C9 122.9(3) . .
C9 C8 C2 121.1(3) . .
C8 C9 H9 120.6 . .
C10 C9 C8 118.7(3) . .
C10 C9 H9 120.6 . .
C9 C10 H10 120.6 . .
C11 C10 C9 118.8(3) . .
C11 C10 H10 120.6 . .
C10 C11 H11 120.7 . .
C10 C11 C12 118.7(3) . .
C12 C11 H11 120.7 . .
N5 C12 C11 123.6(3) . .
N5 C12 H12 118.2 . .
C11 C12 H12 118.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.832(2) .
Ni1 N1 1.832(2) 3_667
Ni1 N3 1.841(2) 3_667
Ni1 N3 1.841(2) .
N1 H1 0.9010 .
N1 C1 1.308(3) .
N2 C1 1.338(4) .
N2 C2 1.339(3) .
N3 H3 0.8650 .
N3 C2 1.307(3) .
N4 C3 1.331(4) .
N4 C7 1.334(4) .
N5 C8 1.331(4) .
N5 C12 1.331(4) .
C1 C7 1.498(4) .
C2 C8 1.495(4) .
C3 H3A 0.9500 .
C3 C4 1.376(4) .
C4 H4 0.9500 .
C4 C5 1.372(5) .
C5 H5 0.9500 .
C5 C6 1.381(4) .
C6 H6 0.9500 .
C6 C7 1.381(4) .
C8 C9 1.381(4) .
C9 H9 0.9500 .
C9 C10 1.380(4) .
C10 H10 0.9500 .
C10 C11 1.367(4) .
C11 H11 0.9500 .
C11 C12 1.375(4) .
C12 H12 0.9500 .
