Highly Regioselective Difluoroalkylarylation of Butadiene through a Nickel-Catalyzed Tandem Radical Process
Ma, Shucheng; Li, Fangjie; Zhang, Guisheng; Shi, Lei; Wang, Xiaoming; ACS Catalysis  (2021) 14848–14853; doi:10.1021/acscatal.1c04237

data_4519143
_publ_section_title
;
 Highly Regioselective Difluoroalkylarylation of Butadiene through a
 Nickel-Catalyzed Tandem Radical Process
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14848
_journal_page_last               14853
_journal_paper_doi               10.1021/acscatal.1c04237
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H17 F2 N O'
_chemical_formula_sum            'C18 H17 F2 N O'
_chemical_formula_weight         301.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2505(4)
_cell_length_b                   14.9948(6)
_cell_length_c                   10.2309(4)
_cell_measurement_reflns_used    6766
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.20
_cell_measurement_theta_min      3.76
_cell_volume                     1572.53(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      192.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10747
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.919
_diffrn_reflns_theta_min         5.904
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1574 before and 0.0870 after correction. The Ratio of minimum to maximum transmission is 0.6119. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0736P)^2^+0.1643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2498
_reflns_number_total             2923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04237_si_002.cif
_cod_data_source_block           mj21342
_cod_database_code               4519143
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              19578
_shelx_hkl_checksum              86639
_olex2_submission_special_instructions 'No special instructions were received'