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_7131811
_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         'C18 H18 F3 N O5'
_chemical_formula_sum            'C18 H18 F3 N O5'
_chemical_formula_weight         385.342
_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
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                72.122(4)
_cell_angle_beta                 71.882(4)
_cell_angle_gamma                89.575(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6797(10)
_cell_length_b                   9.5445(13)
_cell_length_c                   12.4267(16)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      23.838
_cell_measurement_theta_min      2.253
_cell_volume                     926.8(2)
_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)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9890
_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  0.0000
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9890
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3501
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9890
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         2.25
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1166 before and 0.0800 after correction.
 
For component 2:
 wR2(int) was 0.1247 before and 0.0763 after correction.
 The Ratio of minimum to maximum transmission is 0.87.

Final HKLF 4 output contains 68850 reflections, Rint = 0.1098
 (24854 with I > 3sig(I), Rint = 0.0792)
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             400.360
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.5221
_refine_diff_density_min         -0.3488
_refine_diff_density_rms         0.1053
_refine_ls_d_res_high            0.8197
_refine_ls_d_res_low             9.0405
_refine_ls_goodness_of_fit_ref   1.0453
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0453
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.1037
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1727P)^2^+1.0319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2923
_refine_ls_wR_factor_ref         0.3057
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2755
_reflns_number_total             3497
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc01740k2.cif
_cod_data_source_block           MRY_RS_4esterCF3_0m_4_a
_cod_database_code               7131811
_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:
 C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C18(H18a,H18b,
 H18c)
;
_olex2_submission_special_instructions 'No special instructions were received'