#------------------------------------------------------------------------------
#$Date: 2019-11-17 05:08:40 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/13/7121326.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_7121326
loop_
_publ_author_name
'Su, Xiaojun'
'McCardle, Kaitlin M.'
'Panetier, Julien A.'
'Jurss, Jonah W.'
_publ_section_title
;
 Electrocatalytic CO₂ reduction with nickel complexes supported
 by tunable bipyridyl-N-heterocyclic carbene donors: understanding
 redox-active macrocycles.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3351
_journal_page_last               3354
_journal_paper_doi               10.1039/c8cc00266e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H16 Cl2 N6 Ni O8'
_chemical_formula_sum            'C19 H16 Cl2 N6 Ni O8'
_chemical_formula_weight         585.99
_chemical_name_common            3-Ni(ClO4)2
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_cell_setting           monoclinic
_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-97
_audit_update_record
;
2017-12-16 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.402(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.978(9)
_cell_length_b                   12.184(8)
_cell_length_c                   13.374(9)
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.97
_cell_volume                     2148(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7489
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.8881
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1192
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile, diethyl ether'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0479
_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)+(0.0865P)²+3.0007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1731
_reflns_number_total             2050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc00266e2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7121325--7121327.cif.
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               7121326
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1582(4) 0.0000 0.5038(4) 0.0590(14) Uani 1 2 d S
H1A H 0.2273 0.0000 0.4990 0.071 Uiso 1 2 calc SR
H1B H 0.1649 0.0000 0.5799 0.071 Uiso 1 2 calc SR
C2 C 0.0352(3) 0.1079(3) 0.3571(3) 0.0445(8) Uani 1 1 d .
C3 C 0.1334(3) 0.2009(4) 0.5008(3) 0.0635(11) Uani 1 1 d .
H3 H 0.1818 0.2154 0.5686 0.076 Uiso 1 1 calc R
C4 C 0.0794(3) 0.2750(4) 0.4326(4) 0.0659(11) Uani 1 1 d .
H4 H 0.0814 0.3523 0.4421 0.079 Uiso 1 1 calc R
C5 C -0.0582(3) 0.2696(3) 0.2578(3) 0.0602(10) Uani 1 1 d .
H5A H -0.0386 0.3471 0.2537 0.072 Uiso 1 1 calc R
H5B H -0.1225 0.2694 0.2735 0.072 Uiso 1 1 calc R
C6 C -0.0767(3) 0.2172(3) 0.1514(3) 0.0487(8) Uani 1 1 d .
C7 C -0.1049(3) 0.2839(3) 0.0626(4) 0.0621(10) Uani 1 1 d .
H7 H -0.1049 0.3615 0.0700 0.075 Uiso 1 1 calc R
C8 C -0.1330(3) 0.2371(4) -0.0363(3) 0.0670(12) Uani 1 1 d .
H8 H -0.1520 0.2818 -0.0980 0.080 Uiso 1 1 calc R
C9 C -0.1331(3) 0.1242(4) -0.0449(3) 0.0593(10) Uani 1 1 d .
H9 H -0.1535 0.0905 -0.1128 0.071 Uiso 1 1 calc R
C10 C -0.1035(2) 0.0604(3) 0.0460(3) 0.0449(8) Uani 1 1 d .
N1 N 0.1065(2) 0.0986(3) 0.4553(2) 0.0505(7) Uani 1 1 d .
N2 N 0.0193(2) 0.2172(2) 0.3449(2) 0.0522(7) Uani 1 1 d .
N3 N -0.0743(2) 0.1068(2) 0.1441(2) 0.0421(6) Uani 1 1 d .
O1 O -0.4071(9) 0.0000 0.2398(15) 0.287(9) Uani 1 2 d S
O2 O -0.2739(4) 0.0958(4) 0.2566(3) 0.136(2) Uani 1 1 d .
O3 O -0.3502(10) 0.0000 0.1060(5) 0.216(6) Uani 1 2 d S
O4 O 0.7511(3) 0.4030(3) 0.3218(3) 0.0834(10) Uani 1 1 d .
O5 O 0.8992(4) 0.5000 0.4065(4) 0.0964(17) Uani 1 2 d S
O6 O 0.8306(3) 0.5000 0.2219(3) 0.0622(10) Uani 1 2 d S
Cl1 Cl -0.32734(13) 0.0000 0.21515(11) 0.0637(4) Uani 1 2 d S
Cl2 Cl 0.80752(10) 0.5000 0.31967(10) 0.0504(3) Uani 1 2 d S
Ni1 Ni -0.02252(4) 0.0000 0.25633(4) 0.0390(2) Uani 1 2 d S
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'
Cl Cl 0.1484 0.1585 '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 C1 N1 113.1(4) 6 .
N1 C1 H1A 109.0 6 .
N1 C1 H1A 109.0 . .
N1 C1 H1B 109.0 6 .
N1 C1 H1B 109.0 . .
H1A C1 H1B 107.8 . .
N2 C2 N1 103.7(3) . .
N2 C2 Ni1 126.4(3) . .
N1 C2 Ni1 129.8(3) . .
C4 C3 N1 107.5(4) . .
C4 C3 H3 126.2 . .
N1 C3 H3 126.2 . .
C3 C4 N2 106.4(4) . .
C3 C4 H4 126.8 . .
N2 C4 H4 126.8 . .
N2 C5 C6 115.0(3) . .
N2 C5 H5A 108.5 . .
C6 C5 H5A 108.5 . .
N2 C5 H5B 108.5 . .
C6 C5 H5B 108.5 . .
H5A C5 H5B 107.5 . .
N3 C6 C7 122.0(4) . .
N3 C6 C5 119.4(3) . .
C7 C6 C5 118.3(3) . .
C8 C7 C6 119.4(4) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C7 C8 C9 119.1(4) . .
C7 C8 H8 120.4 . .
C9 C8 H8 120.4 . .
C8 C9 C10 119.6(4) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
N3 C10 C9 121.3(4) . .
N3 C10 C10 114.55(19) . 6
C9 C10 C10 124.1(2) . 6
C2 N1 C3 110.8(3) . .
C2 N1 C1 126.8(3) . .
C3 N1 C1 122.1(3) . .
C2 N2 C4 111.6(3) . .
C2 N2 C5 125.5(3) . .
C4 N2 C5 122.5(3) . .
C6 N3 C10 118.5(3) . .
C6 N3 Ni1 128.8(2) . .
C10 N3 Ni1 112.5(2) . .
O1 Cl1 O3 111.1(10) . .
O1 Cl1 O2 107.4(5) . .
O3 Cl1 O2 108.9(3) . .
O1 Cl1 O2 107.4(5) . 6
O3 Cl1 O2 108.9(3) . 6
O2 Cl1 O2 113.3(4) . 6
O5 Cl2 O4 109.8(2) . .
O5 Cl2 O4 109.8(2) . 6_565
O4 Cl2 O4 111.9(3) . 6_565
O5 Cl2 O6 109.2(3) . .
O4 Cl2 O6 107.98(17) . .
O4 Cl2 O6 107.98(17) 6_565 .
C2 Ni1 C2 89.7(2) . 6
C2 Ni1 N3 174.45(13) . 6
C2 Ni1 N3 92.70(16) 6 6
C2 Ni1 N3 92.70(16) . .
C2 Ni1 N3 174.45(13) 6 .
N3 Ni1 N3 84.49(18) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.440(4) 6
C1 N1 1.440(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 N2 1.352(5) .
C2 N1 1.364(4) .
C2 Ni1 1.864(3) .
C3 C4 1.327(7) .
C3 N1 1.383(5) .
C3 H3 0.9500 .
C4 N2 1.387(5) .
C4 H4 0.9500 .
C5 N2 1.449(5) .
C5 C6 1.501(5) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 N3 1.350(5) .
C6 C7 1.384(5) .
C7 C8 1.372(6) .
C7 H7 0.9500 .
C8 C9 1.380(6) .
C8 H8 0.9500 .
C9 C10 1.385(5) .
C9 H9 0.9500 .
C10 N3 1.361(4) .
C10 C10 1.472(7) 6
N3 Ni1 1.936(3) .
O1 Cl1 1.263(10) .
O2 Cl1 1.398(4) .
O3 Cl1 1.386(7) .
O4 Cl2 1.426(3) .
O5 Cl2 1.415(4) .
O6 Cl2 1.448(4) .
Cl1 O2 1.398(4) 6
Cl2 O4 1.426(3) 6_565
Ni1 C2 1.864(3) 6
Ni1 N3 1.936(3) 6
