Rhodium(I)-Catalyzed Directed Trideuteromethylation of (Hetero)arene C–H Bonds with CD3CO2D
Zhao, Haoqiang; Zeng, Qi; yang, ji; Xu, Bing; Lei, Haimin; Xu, Lijin; Walsh, Patrick; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01581A

data_7158884
_publ_section_title
;
 Rhodium(I)-Catalyzed Directed Trideuteromethylation of (Hetero)arene C--H
 Bonds with CD3CO2D
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01581A
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 F3 N2 O'
_chemical_formula_sum            'C12 H9 F3 N2 O'
_chemical_formula_weight         254.21
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-12 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.038(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.891(5)
_cell_length_b                   11.795(2)
_cell_length_c                   8.809(2)
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.366
_cell_measurement_theta_min      2.998
_cell_volume                     2271.3(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.01
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_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  0.0772
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10800
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.997
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1254 before and 0.0825 after correction. The Ratio of minimum to maximum transmission is 0.7648. 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    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0633
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1506
_reflns_number_total             2598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01581a2.cif
_cod_data_source_block           mo_zhq2018100201_0m
_cod_database_code               7158884
_shelx_shelxl_version_number     2014/7
_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. Rigid bond restraints
 F00E, C00G, F00H, F00I
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F00H, C00G, F00E, F00I
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C00G, F00H, F00E, F00I
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(F00J)=Sof(F00F)=Sof(F0AA)=1-FVAR(1)
 Sof(F00E)=Sof(F00H)=Sof(F00I)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C00A(H00A), C00C(H00E), C00D(H00F), C00F(H00G)
4.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
;
_shelx_res_checksum              75993
_shelx_hkl_checksum              38166
_olex2_submission_special_instructions 'No special instructions were received'