Pd-catalyzed enantioselective reductive Heck reaction of mono-fluoro, <i>gem</i>-difluoro, and trifluoromethyl tethered-alkenes.
Sihag, Naveen; Bhartiya, Hemaang; Jain, Swati; Singh, Jitendra; Reddy, S. Rajagopala; Yadav, M. Ramu; Chemical communications (Cambridge, England) 61 (2025) 11413–11416; doi:10.1039/d5cc01559f

data_7134749
_publ_section_title
;
 Pd-catalyzed enantioselective reductive Heck reaction of mono-fluoro,
 <i>gem</i>-difluoro, and trifluoromethyl tethered-alkenes.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11413
_journal_page_last               11416
_journal_paper_doi               10.1039/d5cc01559f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C11 H10 F2 I N O'
_chemical_formula_sum            'C11 H10 F2 I N O'
_chemical_formula_weight         337.109
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-09-16 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.601(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4768(11)
_cell_length_b                   11.5083(6)
_cell_length_c                   14.1850(8)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.28
_cell_volume                     2460.5(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)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25756
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 1.0000
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         2.23
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.607
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.8050.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_description       block
_exptl_crystal_F_000             1293.696
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.7708
_refine_diff_density_min         -0.8292
_refine_diff_density_rms         0.0811
_refine_ls_d_res_high            0.7641
_refine_ls_d_res_low             9.1469
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0381
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+4.6476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0682
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -26
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2318
_reflns_number_total             2895
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc01559f2.cif
_cod_data_source_block           NS_4F_MF_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134747--7134749.cif.'
_cod_database_code               7134749
_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:
 C3(H3), C5(H5), C6(H6), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c)
;
_olex2_submission_special_instructions 'No special instructions were received'