General C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts.
Truesdell, Blaise L.; Hamby, Taylor B.; Sevov, Christo S.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c01475

data_4134386
_publ_section_title
;
 General C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Cross-Electrophile Coupling
 Reactions Enabled by Overcharge Protection of Homogeneous
 Electrocatalysts.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c01475
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 N5 Ni, C4 H8 O'
_chemical_formula_sum            'C30 H29 N5 Ni O'
_chemical_formula_weight         534.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.105(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8094(12)
_cell_length_b                   9.1663(6)
_cell_length_c                   18.1044(11)
_cell_measurement_reflns_used    5633
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      25.341
_cell_measurement_theta_min      3.013
_cell_volume                     2507.5(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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      120.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Photon II MoTRIUMPH'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Curved-Graphite, Bruker TRIUMPH'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_min         3.230
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.091641
_exptl_absorpt_correction_T_min  0.067885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 49752 reflections, Rint = 0.0872
 (23051 with I > 3sig(I), Rint = 0.0564)
;
_exptl_crystal_colour            Orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       Block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0467P)^2^+1.6776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3282
_reflns_number_total             4555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01475_si_002.cif
_cod_data_source_block           Sevov_TH_NiPh
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_primary' value 'Orange' was changed
to 'orange' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134386
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.934
_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
 O1SB-C4SB = O1SB-C1S
 1.45 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C1S, C3S, O1SB, C4SB
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(H1SC)=Sof(H1SD)=Sof(H3SC)=Sof(H3SD)=Sof(O1SB)=Sof(C4SB)=Sof(H4SC)=
 Sof(H4SD)=1-FVAR(1)
 Sof(H1SA)=Sof(H1SB)=Sof(H3SA)=Sof(H3SB)=Sof(O1S)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C1S(H1SC,H1SD), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C3S(H3SC,
 H3SD), C4S(H4SA,H4SB), C4SB(H4SC,H4SD)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              4840
_shelx_hkl_checksum              79958
_olex2_submission_special_instructions 'No special instructions were received'