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_7713610
_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         'C54 H47 N4 O Y'
_chemical_formula_sum            'C54 H47 N4 O Y'
_chemical_formula_weight         856.86
_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             2022-07-25
_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                85.25(4)
_cell_angle_beta                 76.64(3)
_cell_angle_gamma                74.83(7)
_cell_formula_units_Z            2
_cell_length_a                   10.74(3)
_cell_length_b                   13.66(3)
_cell_length_c                   17.96(5)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.20
_cell_measurement_theta_min      2.20
_cell_volume                     2474(11)
_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 0.996
_diffrn_measured_fraction_theta_max 0.979
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28928
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         1.545
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4832
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0944 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.6481.
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    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     588
_refine_ls_number_reflns         11192
_refine_ls_number_restraints     249
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0823P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1643
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6191
_reflns_number_total             11192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           7j
_cod_original_cell_volume        2473(11)
_cod_database_code               7713610
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.775
_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
 O1-C51 \\sim O1A-C51A
 with sigma of 0.02
 O1-C54 \\sim O1A-C54A
 with sigma of 0.02
 C51-C52 \\sim C51A-C52A
 with sigma of 0.02
 C54-C53 \\sim C54A-C53A
 with sigma of 0.02
 C53-C52 \\sim C53A-C52A
 with sigma of 0.02
 Y1-C51 \\sim Y1-C51A
 with sigma of 0.04
 Y1-C54 \\sim Y1-C54A
 with sigma of 0.04
 O1-C53 \\sim O1A-C53A
 with sigma of 0.04
 O1-C52 \\sim O1A-C52A
 with sigma of 0.04
 C51-C54 \\sim C51A-C54A
 with sigma of 0.04
 C51-C53 \\sim C51A-C53A
 with sigma of 0.04
 C54-C52 \\sim C54A-C52A
 with sigma of 0.04
 Y1-O1 \\sim Y1-O1A
 with sigma of 0.02
 O1A-C54A \\sim O1-C54 \\sim O1-C51 \\sim O1A-C51A
 with sigma of 0.02
 C54A-C53A \\sim C54-C53 \\sim C52-C51 \\sim C52A-C51A
 with sigma of 0.02
 C53A-C52A \\sim C53-C52
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim C51 \\sim C54 \\sim C53 \\sim C52 \\sim C51A \\sim C52A \\sim C53A
\\sim C54A \\sim O1A: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
Uanis(O1A) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C52, C54, C53, C51, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C52A, C54A, C53A, O1A, C51A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=Sof(C53A)=
 Sof(H53C)=Sof(H53D)=Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(O1A)=1-FVAR(1)
 Sof(O1)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C53)=
 Sof(H53A)=Sof(H53B)=Sof(C52)=Sof(H52A)=Sof(H52B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C20(H20), C19(H19)
6.b Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C54(H54A,H54B), C53(H53A,H53B), C52(H52A,H52B), C51A(H51C,
 H51D), C52A(H52C,H52D), C53A(H53C,H53D), C54A(H54C,H54D)
6.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C25(H25), C29(H29), C2(H2), C1(H1), C37(H37), C17(H17), C38(H38),
 C3(H3), C39(H39), C32(H32), C35(H35), C11(H11), C28(H28), C41(H41), C50(H50),
 C27(H27), C7(H7), C13(H13), C26(H26), C16(H16), C8(H8), C15(H15), C10(H10),
 C14(H14), C42(H42), C47(H47), C44(H44), C40(H40), C9(H9), C34(H34), C49(H49),
 C43(H43), C48(H48)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              6639
_shelx_fab_checksum              1584
_olex2_submission_special_instructions 'No special instructions were received'