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_7713605
_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         'C63 H49 N6 S Y, C7 H8'
_chemical_formula_sum            'C70 H57 N6 S Y'
_chemical_formula_weight         1103.18
_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             2022-05-24
_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                92.578(16)
_cell_angle_beta                 90.58(2)
_cell_angle_gamma                93.366(12)
_cell_formula_units_Z            2
_cell_length_a                   11.948(14)
_cell_length_b                   14.873(16)
_cell_length_c                   16.154(17)
_cell_measurement_reflns_used    4811
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      20.60
_cell_measurement_theta_min      2.25
_cell_volume                     2863(5)
_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 0.987
_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  0.0839
_diffrn_reflns_av_unetI/netI     0.1371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         1.262
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5400
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0925 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7242.
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    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         13018
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6489
_reflns_number_total             13018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           2i
_cod_database_code               7713605
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.810
_shelx_estimated_absorpt_t_min   0.793
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H20(0.049) H19(0.05) H37(0.055) H22A(0.072) H22B(0.072)
 H22C(0.072) H1(0.059) H39(0.058) H3(0.062) H38(0.064) H31(0.06) H2(0.072)
 H25(0.07) H11(0.071) H17(0.066) H52(0.072) H48(0.075) H29(0.069) H35(0.065)
 H56(0.064) H53(0.065) H32(0.078) H13(0.074) H7(0.074) H16(0.086) H33(0.081)
 H10(0.084) H15(0.093) H61(0.08) H26(0.092) H34(0.081) H28(0.092) H51(0.093)
 H46(0.081) H8(0.09) H14(0.092) H57(0.102) H42(0.089) H9(0.094) H27(0.1)
 H63(0.114) H55(0.081) H44(0.119) H45(0.11) H49(0.102) H50(0.107) H62(0.102)
 H43(0.122) H58(0.124) H66(0.171) H70(0.176) H69(0.204) H67(0.208) H68(0.207)
 H64A(0.261) H64B(0.261) H64C(0.261)
 Fixed X: H20(0.11369) H19(0.068136) H37(0.581303) H22A(0.470002)
 H22B(0.424664) H22C(0.471114) H1(0.517456) H39(0.559506) H3(0.454552)
 H38(0.685284) H31(0.337631) H2(0.593885) H25(0.465045) H11(0.290447)
 H17(0.213667) H52(0.670396) H48(0.498444) H29(0.282936) H35(0.189037)
 H56(0.50465) H53(0.097778) H32(0.234796) H13(0.051067) H7(0.238739)
 H16(0.054751) H33(0.112474) H10(0.308142) H15(-0.102518) H61(0.069073)
 H26(0.501445) H34(0.086531) H28(0.320401) H51(0.834178) H46(0.422404)
 H8(0.253696) H14(-0.107197) H57(-0.044428) H42(0.258007) H9(0.289862)
 H27(0.434514) H63(-0.254367) H55(0.443046) H44(0.105276) H45(0.26397)
 H49(0.662669) H50(0.828045) H62(-0.108027) H43(0.100643) H58(-0.221587) H66(-
 0.026621) H70(0.211017) H69(0.31457) H67(0.084817) H68(0.250361) H64A(-
 0.007393) H64B(0.067699) H64C(-0.042037)
 Fixed Y: H20(0.798138) H19(0.642517) H37(0.906213) H22A(0.69325)
 H22B(0.592311) H22C(0.630554) H1(0.644382) H39(0.854257) H3(0.419829)
 H38(0.917186) H31(0.97328) H2(0.500754) H25(0.924684) H11(0.346393)
 H17(0.497327) H52(0.772312) H48(0.657508) H29(0.691652) H35(0.886413)
 H56(0.966762) H53(0.933836) H32(1.100071) H13(0.46332) H7(0.535494)
 H16(0.441499) H33(1.121477) H10(0.242689) H15(0.392682) H61(0.661819)
 H26(0.897863) H34(1.013314) H28(0.665314) H51(0.76414) H46(0.55725)
 H8(0.430194) H14(0.407984) H57(0.871708) H42(0.780377) H9(0.282804)
 H27(0.766267) H63(0.665389) H55(1.112247) H44(0.537907) H45(0.470807)
 H49(0.65081) H50(0.704785) H62(0.5941) H43(0.691482) H58(0.803265)
 H66(0.872044) H70(0.926009) H69(1.001793) H67(0.943338) H68(1.021221)
 H64A(0.888864) H64B(0.806293) H64C(0.809905)
 Fixed Z: H20(0.588796) H19(0.645247) H37(0.523347) H22A(0.533791)
 H22B(0.522763) H22C(0.609213) H1(0.823449) H39(0.762465) H3(0.682013)
 H38(0.657881) H31(0.643091) H2(0.779891) H25(0.424194) H11(0.64102)
 H17(0.808239) H52(0.920739) H48(1.103319) H29(0.424586) H35(0.429203)
 H56(0.920975) H53(0.808183) H32(0.643618) H13(0.591312) H7(0.479681)
 H16(0.874277) H33(0.536243) H10(0.53335) H15(0.798366) H61(0.845845)
 H26(0.285679) H34(0.431028) H28(0.28605) H51(0.996281) H46(0.960048)
 H8(0.372234) H14(0.657762) H57(0.734131) H42(1.006308) H9(0.39847)
 H27(0.218015) H63(0.787036) H55(0.901688) H44(1.033703) H45(0.993947)
 H49(1.178419) H50(1.125144) H62(0.841752) H43(1.040541) H58(0.732397)
 H66(1.09761) H70(1.265541) H69(1.170848) H67(0.998032) H68(1.039619)
 H64A(1.29388) H64B(1.282938) H64C(1.229464)
;
_shelx_res_checksum              87534
_olex2_submission_special_instructions 'No special instructions were received'