Photoinduced Ni-catalyzed carbohalogenation of monofluoro, gem-difluoro, and trifluoromethyl tethered alkenes
Sharma, Ruchi; Sihag, Naveen; Gupta, Poorvi; Manna, Kuntal; Yadav, M. Ramu; Chemical Communications 61 (2025) 7273–7276; doi:10.1039/D5CC01034A

data_7134400
_publ_section_title
;
 Photoinduced Ni-catalyzed carbohalogenation of monofluoro, gem-difluoro,
 and trifluoromethyl tethered alkenes
;
_journal_issue                   40
_journal_name_full               'Chemical Communications'
_journal_page_first              7273
_journal_page_last               7276
_journal_paper_doi               10.1039/D5CC01034A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C11 H11 F I N O'
_chemical_formula_sum            'C11 H11 F I N O'
_chemical_formula_weight         319.11
_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
_audit_update_record
;
2024-12-25 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.747(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1305(4)
_cell_length_b                   11.7122(2)
_cell_length_c                   16.4642(4)
_cell_measurement_reflns_used    5148
_cell_measurement_temperature    297.06(10)
_cell_measurement_theta_max      81.35
_cell_measurement_theta_min      3.65
_cell_volume                     2335.05(11)
_diffrn_ambient_temperature      297.06(10)
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9747
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1651
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9747
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16979
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9747
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         81.35
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    21.475
_exptl_absorpt_correction_T_max  0.061
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_description       block
_exptl_crystal_F_000             1232.0
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.1941
_refine_diff_density_min         -2.3702
_refine_diff_density_rms         0.3504
_refine_ls_d_res_high            0.7798
_refine_ls_d_res_low             12.1092
_refine_ls_goodness_of_fit_ref   1.2405
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5017
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.2399
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.1050
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2914
_refine_ls_wR_factor_ref         0.2995
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4272
_reflns_number_total             5148
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc01034a2.cif
_cod_data_source_block           RSK-MF-S1_auto
_cod_depositor_comments
'Adding full bibliography for 7134398--7134400.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134400
_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. Restrained distances
 C25-I3 \\sim C25-I3a
 with sigma of 0.02
 C10-I2 \\sim C10-I2a
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(I3a)
4. Others
 Fixed Sof: I2(0.5) I3(0.5) I3a(0.5) I2a(0.5) H10(0.5) H10a(0.5) H25(0.5)
 H25a(0.5)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C10(H10a), C25(H25), C25(H25a)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C20(H20), C19(H19), C18(H18), C17(H17)
5.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C29(H29a,H29b,H29c), C30(H30a,H30b,
 H30c)
;