Palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid with 2-alkynylanilines.
Zhang, Jinhui; Mao, Lihua; Liu, Chao; Tan, Xiangwen; Wu, Jiahao; Wei, Xuefeng; Wu, Wanqing; Jiang, Huanfeng; Chemical communications (Cambridge, England) 60 (2024) 9404–9407; doi:10.1039/d4cc03099k

data_7133432
_publ_section_title
;
 Palladium-catalyzed 1,1-aminoxylation of 3-butenoic acid with
 2-alkynylanilines.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9404
_journal_page_last               9407
_journal_paper_doi               10.1039/d4cc03099k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 F N O2'
_chemical_formula_sum            'C18 H14 F N O2'
_chemical_formula_weight         295.30
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-03-01 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.289(2)
_cell_angle_beta                 110.312(2)
_cell_angle_gamma                107.388(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2770(6)
_cell_length_b                   9.5602(6)
_cell_length_c                   9.7665(6)
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.185
_cell_measurement_theta_min      2.584
_cell_volume                     713.26(8)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8815
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.584
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1628 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.7868. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0358P)^2^+0.1896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1888
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03099k2.cif
_cod_data_source_block           zj1018_0m
_cod_depositor_comments          'Adding full bibliography for 7133432.cif.'
_cod_database_code               7133432
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C18(H18), C8(H8), C12(H12), C6(H6), C14(H14), C16(H16),
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'