Ligand-free Pd-catalyzed double Heck reaction of <i>N</i>-(<i>o</i>-bromoaryl)acrylamides with α-F/CF<sub>3</sub>-acrylates.
Sharma, Ruchi; Jain, Swati; Sihag, Naveen; Yadav, M. Ramu; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc01740k

data_7131813
_publ_section_title
;
 Ligand-free Pd-catalyzed double Heck reaction of
 <i>N</i>-(<i>o</i>-bromoaryl)acrylamides with
 &#x3b1;-F/CF<sub>3</sub>-acrylates.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc01740k
_journal_year                    2023
_chemical_formula_moiety         'C15 H15 Br F N O3'
_chemical_formula_sum            'C15 H15 Br F N O3'
_chemical_formula_weight         356.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-03-19 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.053(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.012(5)
_cell_length_b                   11.607(4)
_cell_length_c                   8.318(2)
_cell_measurement_reflns_used    8983
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.194
_cell_measurement_theta_min      2.168
_cell_volume                     1543.7(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            43441
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9961
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         2.17
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8395.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             720.0
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.7450
_refine_diff_density_min         -0.8509
_refine_diff_density_rms         0.0713
_refine_ls_d_res_high            0.8277
_refine_ls_d_res_low             9.3928
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+1.0438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2320
_reflns_number_total             2848
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc01740k2.cif
_cod_data_source_block           HK25223_0ma_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7131813
_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 Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C11(H11)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C14(H14a,H14b,H14c), C15(H15a,H15b,H15c)
;
_olex2_submission_special_instructions 'No special instructions were received'