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_7131812
_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         'C8 H8 F2 O4'
_chemical_formula_sum            'C8 H8 F2 O4'
_chemical_formula_weight         206.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-29 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                102.961(2)
_cell_angle_beta                 109.449(2)
_cell_angle_gamma                96.622(2)
_cell_formula_units_Z            1
_cell_length_a                   5.6570(4)
_cell_length_b                   6.5148(4)
_cell_length_c                   6.5836(5)
_cell_measurement_reflns_used    3817
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      3.28
_cell_volume                     218.14(3)
_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      301.00
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9967
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.9962
_diffrn_reflns_Laue_measured_fraction_max 0.9967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5448
_diffrn_reflns_point_group_measured_fraction_full 0.9962
_diffrn_reflns_point_group_measured_fraction_max 0.9967
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         3.28
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1562 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9049.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             106.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.1849
_refine_diff_density_min         -0.1439
_refine_diff_density_rms         0.0341
_refine_ls_d_res_high            0.7981
_refine_ls_d_res_low             6.2116
_refine_ls_goodness_of_fit_ref   1.1251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     65
_refine_ls_number_reflns         898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1251
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.0503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              7
_reflns_limit_k_min              -8
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                824
_reflns_number_total             901
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc01740k2.cif
_cod_data_source_block           VS_297SPOT1_0m_a_a
_cod_database_code               7131812
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'