Chemodivergent Nickel(0)-Catalyzed Arene C‒F Activation with Alkynes: Unprecedented C‒F/C‒H Double Insertion
Capdevila, Lorena; Meyer, Tjark H.; Roldán-Gómez, Steven; Luis, Josep M.; Ackermann, Lutz; Ribas, Xavi; ACS Catalysis  (2019) 11074–; doi:10.1021/acscatal.9b03620

data_4515255
_publ_section_title
;
 Chemodivergent Nickel(0)-Catalyzed Arene C--F Activation with Alkynes:
 Unprecedented C--F/C--H Double Insertion
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11074
_journal_paper_doi               10.1021/acscatal.9b03620
_journal_year                    2019
_chemical_formula_moiety         'C44 H30 N2 Ni O, C H Cl3'
_chemical_formula_sum            'C45 H31 Cl3 N2 Ni O'
_chemical_formula_weight         780.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.93(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.600(11)
_cell_length_b                   15.771(11)
_cell_length_c                   16.342(10)
_cell_measurement_reflns_used    190
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      22.2249
_cell_measurement_theta_min      3.6793
_cell_volume                     3960(5)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator
'doubly curved silicon crystal Bruker Triumph'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            91838
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Ceramic x-ray tube'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'intense red-black'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         9082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0299P)^2^+2.8503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                7848
_reflns_number_total             9082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03620_si_002.cif
_cod_data_source_block           LC_L4_p58
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' 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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        3960.(5)
_cod_database_code               4515255
_shelx_res_checksum              43094
_shelx_hkl_checksum              71449
_shelx_fab_checksum              82052