Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C‒H Activation Leads to Z-Selective Coupling of Acrylates
Herbort, James H.; Lalisse, Remy F.; Hadad, Christopher M.; RajanBabu, T. V.; ACS Catalysis  (2021) 9605–9617; doi:10.1021/acscatal.1c02530

data_4518899
_publ_section_title
;
 Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of
 1,6-Enynes: An Uncommon cis-\b-C--H Activation Leads to Z-Selective
 Coupling of Acrylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9605
_journal_page_last               9617
_journal_paper_doi               10.1021/acscatal.1c02530
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H25 F N2 O4 S'
_chemical_formula_sum            'C29 H25 F N2 O4 S'
_chemical_formula_weight         516.57
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.05 svn.r0a1fe1be for OlexSys, GUI svn.r6182)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.7640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5115(7)
_cell_length_b                   10.1690(4)
_cell_length_c                   15.2635(6)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.079
_cell_measurement_theta_min      3.018
_cell_volume                     2506.32(17)
_computing_cell_refinement       'SAINT v8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_min         3.019
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.0943
_exptl_absorpt_correction_T_min  0.0700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0488 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.7423.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       Block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.238
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5510
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+1.2183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                5243
_reflns_number_total             5510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02530_si_005.cif
_cod_data_source_block           RBabu_JHH-4269-1
_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.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4518899
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_shelx_res_checksum              86033
_shelx_hkl_checksum              31334
_olex2_submission_special_instructions 'No special instructions were received'