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_7713609
_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         'C26 H21 N3'
_chemical_formula_sum            'C26 H21 N3'
_chemical_formula_weight         375.46
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
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2022-08-13 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
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_cell_angle_alpha                76.10(3)
_cell_angle_beta                 74.76(3)
_cell_angle_gamma                89.66(3)
_cell_formula_units_Z            2
_cell_length_a                   9.90(3)
_cell_length_b                   10.39(3)
_cell_length_c                   10.65(3)
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.13
_cell_measurement_theta_min      2.49
_cell_volume                     1024(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 0.998
_diffrn_measured_fraction_theta_max 0.982
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12167
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.023
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0778 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8509.
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    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01714a2.cif
_cod_data_source_block           8a
_cod_original_cell_volume        1025(5)
_cod_database_code               7713609
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.063) H18(0.056) H7(0.061) H15(0.058) H13(0.057) H17(0.061)
 H12(0.064) H3(0.065) H26(0.063) H16(0.062) H6(0.071) H5(0.071) H25(0.073)
 H4(0.075) H22(0.075) H11(0.076) H9(0.076) H24(0.084) H23(0.089) H10(0.09)
 Fixed X: H2(0.246374) H1(0.370292) H18(0.186685) H7(0.292512) H15(0.082235)
 H13(0.133695) H17(0.079862) H12(0.236003) H3(0.157544) H26(0.070023)
 H16(0.025343) H6(0.271058) H5(0.197151) H25(0.077863) H4(0.137236)
 H22(0.484984) H11(0.472319) H9(0.504529) H24(0.288764) H23(0.49234)
 H10(0.605663)
 Fixed Y: H2(0.521192) H1(0.519258) H18(0.111541) H7(0.86701) H15(0.293686)
 H13(0.761274) H17(-0.019335) H12(0.914462) H3(0.497805) H26(0.262089)
 H16(0.073795) H6(0.931161) H5(0.779511) H25(0.193096) H4(0.563118)
 H22(0.338533) H11(0.972254) H9(0.723409) H24(0.18815) H23(0.262649)
 H10(0.875638)
 Fixed Z: H2(0.481061) H1(0.212243) H18(0.407349) H7(0.700687) H15(0.772904)
 H13(0.463669) H17(0.615631) H12(0.265921) H3(0.914896) H26(0.245081)
 H16(0.798625) H6(0.897105) H5(1.10135) H25(0.053119) H4(1.109445) H22(0.12129)
 H11(0.206896) H9(0.545363) H24(-0.099639) H23(-0.06686) H10(0.346178)
;
_shelx_res_checksum              91253
_olex2_submission_special_instructions 'No special instructions were received'