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_7134398
_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         'C10 H6 Cl F2 I N O, C2 H3'
_chemical_formula_sum            'C12 H9 Cl F2 I N O'
_chemical_formula_weight         383.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-09-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6441(15)
_cell_length_b                   11.7421(19)
_cell_length_c                   24.791(5)
_cell_measurement_reflns_used    7028
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.46
_cell_volume                     2516.3(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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      302.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9805
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.873
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1876 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.9071.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+15.4561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             2224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01034a2.cif
_cod_data_source_block           RS_4Cl_CF2I_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134398--7134400.cif.'
_cod_database_code               7134398
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.636
_olex2_refinement_description
;
1. Restrained distances
 C8-C1 \\sim C8-C1A
 with sigma of 0.02
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              86300
_shelx_hkl_checksum              10537
_olex2_submission_special_instructions 'No special instructions were received'