Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.
Shevick, Sophia L.; Obradors, Carla; Shenvi, Ryan A.; Journal of the American Chemical Society 140 (2018) 12056–12068; doi:10.1021/jacs.8b06458

data_4132787
_publ_section_title
;
 Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12056
_journal_page_last               12068
_journal_paper_doi               10.1021/jacs.8b06458
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety
'1(C36 H56 Co N2 O4), 2(C6 H12 N2 O), C F3 O3 S, 0.5(C6 H6)'
_chemical_formula_sum            'C52 H83 Co F3 N6 O9 S'
_chemical_formula_weight         1084.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.187(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.483(3)
_cell_length_b                   21.984(2)
_cell_length_c                   20.235(2)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.804
_cell_measurement_theta_min      2.227
_cell_volume                     11314(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            124565
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.356
_diffrn_reflns_theta_min         2.096
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.0439
_exptl_absorpt_correction_T_min  0.0252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.5740.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'Brownish Purple'
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    Purple
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       Block
_exptl_crystal_F_000             4632
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.109(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1419
_refine_ls_number_reflns         19880
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0312P)^2^+6.2164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                15762
_reflns_number_total             19880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06458_si_004.cif
_cod_data_source_block           Shenvi94
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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_modifier' value 'Brownish' was
changed to 'brownish' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        11313.3(19)
_cod_database_code               4132787
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.891(11) 0.109(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1S'-H1SA = O1S'-H1SB = O2S-H2SD = O2S-H2SC
 0.95 with sigma of 0.02
 H1SA-H1SB
 1.45 with sigma of 0.02
 H2SD-H2SC
 1.45 with sigma of 0.02
 O2SB-H2SA = O2S'-H2SA = O2SB-H2SB = O2S'-H2SB
 0.95 with sigma of 0.02
 O1S-H1SD = O1S-H1SC
 0.95 with sigma of 0.02
 H1SD-H1SC
 1.45 with sigma of 0.02
 C11B-C12B
 1.5 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O2SB) = Uanis(O2S')
Uanis(C11B) = Uanis(C11')
Uanis(C9') = Uanis(C9B)
Uanis(C8B) = Uanis(C8')
Uanis(C13B) = Uanis(C13')
5. Rigid body (RIGU) restrains
 C4', C25', C27', C28', C25B, C26B, C27B, C28B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N1', N2', C10', C8', C9', C11', C12', C13', C8B, C9B, C11B, C12B, C13B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C25B)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27B)=Sof(H27D)=
 Sof(H27E)=Sof(H27F)=Sof(C28B)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C25')=Sof(C26')=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27')=Sof(H27A)=
 Sof(H27B)=Sof(H27C)=Sof(C28')=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(O2SB)=1-FVAR(2)
 Sof(O2S')=FVAR(2)
 Fixed Sof: H10A(0.75) H10B(0.75) H10C(0.25) H10D(0.25) C8'(0.75) H8'(0.75)
 C9'(0.75) H9'(0.75) C11'(0.75) H11A(0.75) H11B(0.75) C12'(0.75) H12A(0.75)
 H12B(0.75) C13'(0.75) H13A(0.75) H13B(0.75) C8B(0.25) H8B(0.25) C9B(0.25)
 H9B(0.25) C11B(0.25) H11C(0.25) H11D(0.25) C12B(0.25) H12C(0.25) H12D(0.25)
 C13B(0.25) H13C(0.25) H13D(0.25)
7.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C8'(H8'), C9'(H9'), C8B(H8B), C9B(H9B)
7.b Secondary CH2 refined with riding coordinates:
 C10(H10E,H10F), C11(H11E,H11F), C12(H12E,H12F), C13(H13E,H13F), C10'(H10A,
 H10B), C10'(H10C,H10D), C11'(H11A,H11B), C12'(H12A,H12B), C13'(H13A,H13B),
 C11B(H11C,H11D), C12B(H12C,H12D), C13B(H13C,H13D), C2D(H2DA,H2DB), C3D(H3DA,
 H3DB), C4D(H4DA,H4DB), C8D(H8DA,H8DB), C9D(H9DA,H9DB), C10D(H10G,H10H),
 C14D(H14A,H14B), C15D(H15A,H15B), C16D(H16A,H16B), C20D(H20A,H20B), C21D(H21A,
 H21B), C22D(H22G,H22H)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C14(H14), C16(H16), C18(H18), C3'(H3'), C5'(H5'),
 C7'(H7'), C14'(H14'), C16'(H16'), C18'(H18'), C1S(H1S), C2S(H2S), C3S(H3S),
 C4S(H4S), C5S(H5S), C6S(H6S)
7.d Idealised Me refined as rotating group:
 C22(H22D,H22E,H22F), C23(H23D,H23E,H23F), C24(H24D,H24E,H24F), C26(H26G,H26H,
 H26I), C27(H27G,H27H,H27I), C28(H28G,H28H,H28I), C30(H30D,H30E,H30F), C31(H31D,
 H31E,H31F), C32(H32D,H32E,H32F), C34(H34D,H34E,H34F), C35(H35D,H35E,H35F),
 C36(H36D,H36E,H36F), C22'(H22A,H22B,H22C), C23'(H23A,H23B,H23C), C24'(H24A,
 H24B,H24C), C30'(H30A,H30B,H30C), C31'(H31A,H31B,H31C), C32'(H32A,H32B,H32C),
 C34'(H34A,H34B,H34C), C35'(H35A,H35B,H35C), C36'(H36A,H36B,H36C), C26'(H26A,
 H26B,H26C), C27'(H27A,H27B,H27C), C28'(H28A,H28B,H28C), C26B(H26D,H26E,H26F),
 C27B(H27D,H27E,H27F), C28B(H28D,H28E,H28F), C5D(H5DA,H5DB,H5DC), C6D(H6DA,H6DB,
 H6DC), C11D(H11G,H11H,H11I), C12D(H12G,H12H,H12I), C17D(H17A,H17B,H17C),
 C18D(H18A,H18B,H18C), C23D(H23G,H23H,H23I), C24D(H24G,H24H,H24I)
;
_shelx_res_checksum              59390
_shelx_hkl_checksum              70220
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'