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_7713603
_publ_section_title
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 Aryl C--H bond functionalization with diphenyldiazomethane induced by
 rare-earth metal alkyl complexes
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01714A
_journal_year                    2023
_chemical_formula_moiety         'C56 H49 Lu N4 O, 0.5(C7 H8)'
_chemical_formula_sum            'C59.5 H53 Lu N4 O'
_chemical_formula_weight         1015.03
_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             2022-08-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
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_audit_update_record
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2022-08-13 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.7390(10)
_cell_angle_beta                 107.4760(10)
_cell_angle_gamma                117.4340(10)
_cell_formula_units_Z            2
_cell_length_a                   13.8291(7)
_cell_length_b                   14.0855(7)
_cell_length_c                   14.6541(7)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.541
_cell_measurement_theta_min      2.410
_cell_volume                     2377.6(2)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28725
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.580
_diffrn_reflns_theta_min         1.481
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.122
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0456 after correction.
The Ratio of minimum to maximum transmission is 0.6786.
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    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1034
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         11329
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9291
_reflns_number_total             11329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           4a'
_cod_original_formula_sum        'C59.50 H53 Lu N4 O'
_cod_database_code               7713603
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.652
_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. Uiso/Uaniso restraints and constraints
C62 \\sim C61 \\sim C57 \\sim C63 \\sim C60 \\sim C58 \\sim C59: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C62, C61, C57, C63, C60, C58, C59
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Fixed Sof: C62(0.5) C61(0.5) H61(0.5) C60(0.5) H60(0.5) C59(0.5) H59(0.5)
 C58(0.5) H58(0.5) C57(0.5) H57(0.5) C63(0.5) H63A(0.5) H63B(0.5) H63C(0.5)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C56(H56A,H56B), C55(H55A,H55B), C54(H54A,H54B)
5.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C13(H13), C17(H17), C14(H14), C35(H35), C7(H7), C3(H3), C31(H31),
 C38(H38), C32(H32), C11(H11), C15(H15), C39(H39), C52(H52), C29(H29), C48(H48),
  C8(H8), C25(H25), C33(H33), C16(H16), C2(H2), C1(H1), C34(H34), C26(H26),
 C28(H28), C49(H49), C27(H27), C42(H42), C9(H9), C10(H10), C50(H50), C46(H46),
 C51(H51), C61(H61), C60(H60), C59(H59), C58(H58), C57(H57), C43(H43), C44(H44),
  C45(H45)
5.d Fitted hexagon refined as free rotating group:
 C62(C61,C60,C59,C58,C57)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C63(H63A,H63B,H63C)
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_shelx_res_checksum              72093
_olex2_submission_special_instructions 'No special instructions were received'