A photoinduced transient activating strategy for late-stage chemoselective C(sp3)–H trifluoromethylation of azines
Huang, Mengjun; Ma, Jiawei; Zou, Zhenlei; Li, Heyin; Liu, Jiyang; Kong, Lingyu; Pan, Yi; Zhang, Weigang; Liang, Yong; Wang, Yi; Chemical Science  (2022) –; doi:10.1039/D2SC03989C

data_1567561
_publ_section_title
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 A photoinduced transient activating strategy for late-stage
 chemoselective C(sp3)--H trifluoromethylation of azines
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03989C
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 F3 N2 O'
_chemical_formula_sum            'C21 H19 F3 N2 O'
_chemical_formula_weight         372.38
_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
_audit_creation_date             2021-04-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-07 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 91.06(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   8.832(2)
_cell_length_b                   11.476(2)
_cell_length_c                   17.721(4)
_cell_measurement_reflns_used    3840
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.30
_cell_volume                     1795.8(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16006
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.114
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8857.
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    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.7205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2840
_reflns_number_total             4117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03989c2.cif
_cod_data_source_block           2_a
_cod_original_cell_volume        1796.0(7)
_cod_database_code               1567561
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H009(0.029) H00A(0.032) H00B(0.032) H00C(0.034) H00D(0.034)
 H00E(0.039) H00H(0.042) H00I(0.044) H00J(0.043) H00K(0.047) H00L(0.048)
 H00M(0.045) H00N(0.048) H00F(0.067) H00G(0.067) H00O(0.067) H00P(0.062)
 H00Q(0.058) H00R(0.065)
 Fixed X: H009(0.3462) H00A(0.2808) H00B(0.1228) H00C(0.0606) H00D(0.2164)
 H00E(0.4437) H00H(-0.0462) H00I(0.4264) H00J(0.3365) H00K(-0.0388)
 H00L(0.6464) H00M(0.6545) H00N(0.4764) H00F(0.0464) H00G(0.198) H00O(0.1226)
 H00P(0.7252) H00Q(0.586) H00R(0.7792)
 Fixed Y: H009(0.3954) H00A(0.5717) H00B(0.521) H00C(0.4885) H00D(0.5436)
 H00E(0.4939) H00H(0.3409) H00I(0.2515) H00J(0.1429) H00K(0.2286) H00L(0.3436)
 H00M(0.4653) H00N(0.2131) H00F(0.1072) H00G(0.0371) H00O(0.0536) H00P(0.1911)
 H00Q(0.1178) H00R(0.1451)
 Fixed Z: H009(0.4152) H00A(0.4746) H00B(0.4954) H00C(0.366) H00D(0.3451)
 H00E(0.3007) H00H(0.2877) H00I(0.0908) H00J(0.3055) H00K(0.1803) H00L(0.1254)
 H00M(0.2306) H00N(0.5168) H00F(0.4688) H00G(0.4776) H00O(0.3976) H00P(0.481)
 H00Q(0.2707) H00R(0.3577)
;
_olex2_submission_special_instructions 'No special instructions were received'