Visible-Light-Induced Mn(0)-Catalyzed Direct C3 Mono-, Di- and Perfluoroalkylations of 2H-Indazoles
Laru, Sudip; Bhattacharjee, Suvam; Hajra, Alakananda; Chemical Communications  (2022) –; doi:10.1039/D2CC05021H

data_7130977
_publ_section_title
;
 Visible-Light-Induced Mn(0)-Catalyzed Direct C&#xF02D;3 Mono-, Di- and
 Perfluoroalkylations of 2H-Indazoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05021H
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 F5 N2 O3 P'
_chemical_formula_sum            'C19 H18 F5 N2 O3 P'
_chemical_formula_weight         448.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2ck3xz
_audit_creation_date             2022-07-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.77(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.144(2)
_cell_length_b                   9.764(2)
_cell_length_c                   26.580(5)
_cell_measurement_reflns_used    5631
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.23
_cell_volume                     2088.9(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0394
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30821
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.550
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1350 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1026P)^2^+2.1775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2143
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2570
_reflns_number_total             3682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05021h2.cif
_cod_data_source_block           vb_0m_a
_cod_database_code               7130977
_shelx_shelxl_version_number     2019/1
_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
 O2-C3
 1.42 with sigma of 0.02
 C3-C4
 1.51 with sigma of 0.02
 O2-C4
 2.37 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
4. Rigid body (RIGU) restrains
 O2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K), C00N(H00N),
 C00O(H00O), C00P(H00P)
5.c Idealised Me refined as rotating group:
 C00S(H00C,H00F,H00H), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              70345
_shelx_hkl_checksum              62576
_olex2_submission_special_instructions 'No special instructions were received'