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_7713601
_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         'C66 H53 Lu N6 O'
_chemical_formula_sum            'C66 H53 Lu N6 O'
_chemical_formula_weight         1121.11
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-09
_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                90
_cell_angle_beta                 108.3480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0687(10)
_cell_length_b                   43.818(3)
_cell_length_c                   20.2354(14)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      21.30
_cell_measurement_theta_min      2.16
_cell_volume                     11840.2(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.991
_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  0.1278
_diffrn_reflns_av_unetI/netI     0.1220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            137606
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_min         1.158
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.712
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4286
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.5748.
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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             4560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.330
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.103
_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     1337
_refine_ls_number_reflns         26877
_refine_ls_number_restraints     984
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0722
_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^)+(0.0443P)^2^+39.0969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14538
_reflns_number_total             26877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           2d'
_cod_depositor_comments
;

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C264 H212 Lu4 N24 O4'
_cod_original_formula_weight         4484.44
_cod_original_formula_moiety         '4(C66 H53 Lu N6 O)'
_cod_original_formula_units_Z            2
_cod_database_code               7713601
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.726
_shelx_estimated_absorpt_t_min   0.704
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C20A(H20A), C19A(H19A), C19(H19), C20(H20)
3.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C7A(H7A), C3A(H3A), C2A(H2A), C11A(H11A), C37A(H37A), C25A(H25A),
 C39A(H39A), C13A(H13A), C58A(H58A), C29A(H29A), C31A(H31A), C56A(H56A),
 C65A(H65A), C17A(H17A), C53A(H53A), C10A(H10A), C25(H25), C53(H53), C8A(H8A),
 C9A(H9A), C26A(H26A), C61A(H61A), C3(H3), C58(H58), C26(H26), C48A(H48A),
 C55A(H55A), C29(H29), C34A(H34A), C16A(H16A), C2(H2), C38A(H38A), C55(H55),
 C14A(H14A), C32A(H32A), C35(H35), C37(H37), C15A(H15A), C27A(H27A), C28A(H28A),
  C33A(H33A), C35A(H35A), C28(H28), C31(H31), C27(H27), C38(H38), C52A(H52A),
 C11(H11), C13(H13), C7(H7), C1(H1), C39(H39), C46A(H46A), C64A(H64A), C34(H34),
  C56(H56), C17(H17), C65(H65), C42A(H42A), C43A(H43A), C16(H16), C10(H10),
 C62A(H62A), C50A(H50A), C44(H44), C9(H9), C61(H61), C42(H42), C33(H33),
 C46(H46), C49A(H49A), C63A(H63A), C14(H14), C51A(H51A), C8(H8), C15(H15),
 C45(H45), C45A(H45A), C64(H64), C32(H32), C43(H43), C63(H63), C44A(H44A),
 C62(H62), C48(H48), C49(H49), C50(H50), C52(H52), C51(H51)
3.c Idealised Me refined as rotating group:
 C22A(H22A,H22B,H22C), C22(H22D,H22E,H22F), C66A(H66A,H66B,H66C), C66(H66D,
 H66E,H66F)
;
_shelx_res_checksum              63229
_shelx_fab_checksum              76663
_olex2_submission_special_instructions 'No special instructions were received'