#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:26:22 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/79/1567907.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_1567907
loop_
_publ_author_name
'Norouziyanlakvan, Somayeh'
'Ferguson, Jonathan'
'Richeson, Darrin'
_publ_section_title
;
 Electrocatalytic hydrogen production from neutral water using an aqueous
 Ni(ii) pincer complex
;
_journal_issue                   24
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              7494
_journal_page_last               7500
_journal_paper_doi               10.1039/D2CY01504H
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C21 H19 Br2 N3 Ni'
_chemical_formula_weight         531.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_update_record
;
2022-08-09 deposited with the CCDC.	2022-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.9980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9809(5)
_cell_length_b                   8.5994(3)
_cell_length_c                   15.5441(5)
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.62
_cell_volume                     2081.43(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1913
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_min         2.616
_exptl_absorpt_coefficient_mu    4.782
_exptl_absorpt_correction_T_max  0.745209
_exptl_absorpt_correction_T_min  0.582612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0309P)²+3.2499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1747
_reflns_number_total             1913
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cy01504h2.cif
_cod_data_source_block           K0960_0m_4_a
_cod_depositor_comments          'Adding full bibliography for 1567907.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1567907
_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_shelxl_version_number     2018/3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61529(2) 0.74239(4) 0.36020(2) 0.03857(11) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.63613(5) 0.250000 0.02412(13) Uani 1 2 d S T P . .
N1 N 0.500000 0.4097(3) 0.250000 0.0255(6) Uani 1 2 d S T P . .
N2 N 0.41830(15) 0.5853(3) 0.33606(16) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.500000 0.0941(5) 0.250000 0.0537(13) Uani 1 2 d S T P . .
H1 H 0.500000 -0.015242 0.250000 0.064 Uiso 1 2 calc R U P . .
C2 C 0.4508(3) 0.1733(4) 0.2982(3) 0.0450(8) Uani 1 1 d . . . . .
H2 H 0.417076 0.119345 0.330689 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4526(2) 0.3347(3) 0.2976(3) 0.0290(6) Uani 1 1 d . . . . .
C4 C 0.40491(19) 0.4404(3) 0.3455(2) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.3472(2) 0.3738(4) 0.3992(3) 0.0455(8) Uani 1 1 d . . . . .
H5A H 0.373230 0.281059 0.429347 0.068 Uiso 1 1 calc R U . . .
H5B H 0.292340 0.347138 0.360824 0.068 Uiso 1 1 calc R U . . .
H5C H 0.338329 0.449803 0.442423 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3756(2) 0.7021(3) 0.3765(2) 0.0298(6) Uani 1 1 d . . . . .
C7 C 0.2916(3) 0.7401(5) 0.3412(3) 0.0553(14) Uani 1 1 d . . . . .
H7 H 0.259785 0.684265 0.292801 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2540(3) 0.8612(6) 0.3774(3) 0.0617(12) Uani 1 1 d . . . . .
H8 H 0.196540 0.887680 0.352784 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2990(3) 0.9430(4) 0.4484(3) 0.0471(8) Uani 1 1 d . . . . .
H9 H 0.272675 1.024724 0.472678 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3824(3) 0.9043(5) 0.4835(3) 0.0525(10) Uani 1 1 d . . . . .
H10 H 0.413697 0.959273 0.532521 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4216(3) 0.7844(5) 0.4473(3) 0.0462(9) Uani 1 1 d . . . . .
H11 H 0.479405 0.759540 0.471158 0.055 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
N1 Ni1 N2 78.07(6) . . ?
N1 Ni1 N2 78.07(6) . 2_655 ?
N2 Ni1 N2 156.15(12) . 2_655 ?
N1 Ni1 Br1 112.412(13) . . ?
N2 Ni1 Br1 96.40(7) . . ?
N2 Ni1 Br1 92.64(7) 2_655 . ?
N1 Ni1 Br1 112.411(13) . 2_655 ?
N2 Ni1 Br1 92.64(7) . 2_655 ?
N2 Ni1 Br1 96.40(7) 2_655 2_655 ?
Br1 Ni1 Br1 135.18(3) . 2_655 ?
C3 N1 C3 122.3(3) . 2_655 ?
C3 N1 Ni1 118.83(16) . . ?
C3 N1 Ni1 118.84(16) 2_655 . ?
C4 N2 C6 121.5(2) . . ?
C4 N2 Ni1 114.67(18) . . ?
C6 N2 Ni1 123.65(17) . . ?
C2 C1 C2 120.9(4) 2_655 . ?
C2 C1 H1 119.6 2_655 . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C3 C2 120.1(3) . . ?
N1 C3 C4 113.5(2) . . ?
C2 C3 C4 126.4(3) . . ?
N2 C4 C3 114.8(2) . . ?
N2 C4 C5 125.4(3) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 119.8(3) . . ?
C7 C6 N2 120.7(3) . . ?
C11 C6 N2 119.3(3) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 119.9(4) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
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
Br1 Ni1 2.3967(3) . ?
Ni1 N1 1.947(3) . ?
Ni1 N2 2.114(2) . ?
Ni1 N2 2.114(2) 2_655 ?
N1 C3 1.338(3) . ?
N1 C3 1.338(3) 2_655 ?
N2 C4 1.278(4) . ?
N2 C6 1.436(3) . ?
C1 C2 1.382(4) 2_655 ?
C1 C2 1.382(4) . ?
C1 H1 0.9400 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.489(4) . ?
C4 C5 1.491(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.370(6) . ?
C6 C11 1.374(6) . ?
C7 C8 1.383(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.369(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5B Br1 0.97 2.97 3.790(4) 143.3 3_445 yes
C11 H11 Br1 0.94 3.07 3.665(4) 123.1 . yes
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 -0.5(2) 2_655 . . . ?
C3 N1 C3 C2 -0.5(2) 2_655 . . . ?
Ni1 N1 C3 C2 179.5(2) . . . . ?
C3 N1 C3 C4 180.0(4) 2_655 . . . ?
Ni1 N1 C3 C4 0.0(4) . . . . ?
C1 C2 C3 N1 1.0(4) . . . . ?
C1 C2 C3 C4 -179.6(5) . . . . ?
C6 N2 C4 C3 178.6(3) . . . . ?
Ni1 N2 C4 C3 2.8(4) . . . . ?
C6 N2 C4 C5 -1.5(5) . . . . ?
Ni1 N2 C4 C5 -177.3(3) . . . . ?
N1 C3 C4 N2 -1.9(5) . . . . ?
C2 C3 C4 N2 178.6(3) . . . . ?
N1 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C4 N2 C6 C7 -77.1(4) . . . . ?
Ni1 N2 C6 C7 98.3(3) . . . . ?
C4 N2 C6 C11 107.8(4) . . . . ?
Ni1 N2 C6 C11 -76.8(4) . . . . ?
C11 C6 C7 C8 0.0(7) . . . . ?
N2 C6 C7 C8 -175.0(4) . . . . ?
C6 C7 C8 C9 -0.6(7) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C7 C6 C11 C10 0.8(7) . . . . ?
N2 C6 C11 C10 175.9(3) . . . . ?
C9 C10 C11 C6 -1.1(7) . . . . ?
