Electrocatalytic reduction of CO2 with CCC-NHC pincer nickel complexes
Cope, James D.; Liyanage, Nalaka P.; Kelley, Paul J.; Denny, Jason A.; Valente, Edward J.; Webster, Charles Edwin; Delcamp, Jared H.; Hollis, T. Keith; Chem. Commun.  (2017) –; doi:10.1039/C6CC06537F

data_7120527
_publ_section_title
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 Electrocatalytic reduction of CO2 with CCC-NHC pincer nickel complexes
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_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C6CC06537F
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H25 Cl N4 Ni'
_chemical_formula_sum            'C20 H25 Cl N4 Ni'
_chemical_formula_weight         415.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8944(11)
_cell_length_b                   11.3015(13)
_cell_length_c                   16.6259(19)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.207
_cell_measurement_theta_min      2.179
_cell_volume                     1859.1(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            57709
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_min         2.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1256 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.7274.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0307
_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/[\s^2^(Fo^2^)+(0.0256P)^2^+0.7660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0628
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4251
_reflns_number_total             4645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc06537f2.cif
_cod_data_source_block           orth
_cod_database_code               7120527
_publcif_datablock.id            {1975d308-8449-4c55-9645-82b7f68ab83e}
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18A-C17 \\sim C18B-C17 \\sim C19A-C18A \\sim C19B-C18B \\sim C19B-C20B \\sim
C20A-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18A) = Uanis(C18B) = Uanis(C19B) = Uanis(C19A) = Uanis(C20A) =
Uanis(C20B)
4. Others
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19C)=
 Sof(H19D)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=
 Sof(H19B)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C17(H17A,H17B), C17(H17C,H17D),
 C18A(H18A,H18B), C19A(H19A,H19B), C18B(H18C,H18D), C19B(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C9(H9), C6(H6), C7(H7), C15(H15), C16(H16)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'