2-Amino-5,6-difluorophenyl-1<i>H</i>-pyrazole-Directed Pd<sup>II</sup> Catalysis: Arylation of Unactivated β-C(sp<sup>3</sup>)-H Bonds.
Yang, Jinyue; Fu, Xiaopan; Tang, Shibiao; Deng, Kezuan; Zhang, Lili; Yang, Xianjin; Ji, Yafei; The Journal of organic chemistry 84 (2019) 10221–10236; doi:10.1021/acs.joc.9b01276

data_4034062
_publ_section_title
;
 2-Amino-5,6-difluorophenyl-1<i>H</i>-pyrazole-Directed Pd<sup>II</sup>
 Catalysis: Arylation of Unactivated \b-C(sp<sup>3</sup>)-H Bonds.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10221
_journal_page_last               10236
_journal_paper_doi               10.1021/acs.joc.9b01276
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C21 H18 F5 N3 O'
_chemical_formula_weight         423.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                81.9550(10)
_cell_angle_beta                 89.1030(10)
_cell_angle_gamma                82.3940(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2336(4)
_cell_length_b                   9.4539(4)
_cell_length_c                   11.6746(6)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.831
_cell_measurement_theta_min      5.233
_cell_volume                     1000.20(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14159
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         2.617
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.063(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3701
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0567P)^2^+0.3307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2846
_reflns_number_total             3701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01276_si_002.cif
_cod_data_source_block           mo_d8v19145_0m
_cod_original_cell_volume        1000.21(8)
_cod_database_code               4034062
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-4
_shelx_res_checksum              11626
_shelx_hkl_checksum              66512