Aryl C–H bond functionalization with diphenyldiazomethane induced by rare-earth metal alkyl complexes
Guo, Dianjun; Rajeshkumar, Thayalan; Zhu, Shan; Yuan, Qingbing; Hong, Dongjing; Zhou, Shuangliu; Zhu, Xiancui; Maron, Laurent; Wang, Shaowu; Dalton Transactions  (2023) –; doi:10.1039/D3DT01714A

data_7713594
_publ_section_title
;
 Aryl C--H bond functionalization with diphenyldiazomethane induced by
 rare-earth metal alkyl complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01714A
_journal_year                    2023
_chemical_formula_moiety         'C69 H59 N6 O Y'
_chemical_formula_sum            'C69 H59 N6 O Y'
_chemical_formula_weight         1077.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-13 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                98.03(5)
_cell_angle_beta                 94.36(5)
_cell_angle_gamma                116.15(5)
_cell_formula_units_Z            2
_cell_length_a                   14.43(7)
_cell_length_b                   16.35(7)
_cell_length_c                   17.84(8)
_cell_measurement_reflns_used    4434
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      19.60
_cell_measurement_theta_min      2.50
_cell_volume                     3696(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_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  0.1406
_diffrn_reflns_av_unetI/netI     0.2286
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41043
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.630
_diffrn_reflns_theta_min         1.414
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5073
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.6805.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    0.967
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         16609
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.1860
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0614P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6462
_reflns_number_total             16609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           2a
_cod_original_cell_volume        3698(28)
_cod_database_code               7713594
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.852
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C20(H20), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C38(H38A,H38B), C37(H37A,H37B), C36(H36A,H36B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C00I(H00I), C2(H2), C00T(H00T), C3(H3), C55(H55), C31(H31),
 C00Y(H00Y), C1(H1), C56(H56), C42(H42), C29(H29), C28(H28), C25(H25), C7(H7),
 C58(H58), C61(H61), C17(H17), C13(H13), C57(H57), C15(H15), C11(H11), C43(H43),
  C52(H52), C46(H46), C33(H33), C16(H16), C35(H35), C44(H44), C32(H32),
 C34(H34), C14(H14), C65(H65), C48(H48), C8(H8), C27(H27), C45(H45), C9(H9),
 C10(H10), C26(H26), C62(H62), C51(H51), C49(H49), C50(H50), C64(H64), C63(H63)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              55444
_shelx_fab_checksum              13646
_olex2_submission_special_instructions 'No special instructions were received'