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_7713598
_publ_section_title
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 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 N6 O Y'
_chemical_formula_sum            'C66 H53 N6 O Y'
_chemical_formula_weight         1035.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-13 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.696(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.84(2)
_cell_length_b                   19.50(3)
_cell_length_c                   24.86(4)
_cell_measurement_reflns_used    8299
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.666
_cell_measurement_theta_min      2.180
_cell_volume                     6153(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.1202
_diffrn_reflns_av_unetI/netI     0.1192
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            71644
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.333
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.7776.
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    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         14096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0548P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7276
_reflns_number_total             14096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           2c
_cod_original_cell_volume        6156(18)
_cod_database_code               7713598
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.827
_shelx_estimated_absorpt_t_min   0.812
_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.a Ternary CH refined with riding coordinates:
 C20(H20), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C25(H25), C37(H37), C2(H2), C42(H42), C17(H17), C13(H13), C38(H38),
 C29(H29), C65(H65), C58(H58), C16(H16), C39(H39), C7(H7), C1(H1), C28(H28),
 C53(H53), C62(H62), C11(H11), C43(H43), C27(H27), C61(H61), C48(H48), C46(H46),
  C26(H26), C52(H52), C31(H31), C55(H55), C64(H64), C35(H35), C15(H15),
 C49(H49), C9(H9), C50(H50), C10(H10), C8(H8), C57(H57), C44(H44), C14(H14),
 C56(H56), C45(H45), C32(H32), C34(H34), C33(H33), C51(H51)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C66(H66A,H66B,H66C)
;
_shelx_res_checksum              29056
_shelx_fab_checksum              45946
_olex2_submission_special_instructions 'No special instructions were received'