A naphthalene-based heterobimetallic triazolylidene Ir<sup>III</sup>/Pd<sup>II</sup> complex: regioselective to regiospecific C-H activation, tandem catalysis and a copper-free Sonogashira reaction.
Majumder, Adhir; Naskar, Rajat; Roy, Pallabi; Mondal, Bhaskar; Garai, Somenath; Maity, Ramananda; Dalton transactions (Cambridge, England : 2003) 52 (2023) 2272–2281; doi:10.1039/d2dt03508a

data_7712220
_publ_section_title
;
 A naphthalene-based heterobimetallic triazolylidene
 Ir<sup>III</sup>/Pd<sup>II</sup> complex: regioselective to regiospecific
 C-H activation, tandem catalysis and a copper-free Sonogashira reaction.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2272
_journal_page_last               2281
_journal_paper_doi               10.1039/d2dt03508a
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C35 H41 I3 Ir N7 Pd'
_chemical_formula_sum            'C35 H41 I3 Ir N7 Pd'
_chemical_formula_weight         1239.05
_chemical_name_systematic        Ir-Pd-I3-L
_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
_audit_creation_date             2023-01-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_audit_update_record
;
2023-01-10 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.497(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4972(6)
_cell_length_b                   16.5680(6)
_cell_length_c                   15.7790(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      71.054
_cell_measurement_theta_min      4.054
_cell_volume                     3786.4(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v2016'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1388
_diffrn_reflns_av_unetI/netI     0.1169
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25748
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        65.080
_diffrn_reflns_theta_max         65.080
_diffrn_reflns_theta_min         4.054
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    30.011
_exptl_absorpt_correction_T_max  0.0954
_exptl_absorpt_correction_T_min  0.0037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1863 before and 0.1081 after correction.
The Ratio of minimum to maximum transmission is 0.0388.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_description       block
_exptl_crystal_F_000             2328
_exptl_crystal_recrystallization_method
'The material was recrystallised from Acetonitrile by layering with dietheyl ether.'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         6.603
_refine_diff_density_min         -2.608
_refine_diff_density_rms         0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6340
_refine_ls_number_restraints     404
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.1010
_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^)+(0.1180P)^2^+130.9534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2339
_refine_ls_wR_factor_ref         0.2485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5090
_reflns_number_total             6340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03508a2.cif
_cod_data_source_block           adhir_pd_ir_0m
_cod_depositor_comments          'Adding full bibliography for 7712220.cif.'
_cod_database_code               7712220
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.153
_shelx_estimated_absorpt_t_min   0.062
_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. Restrained distances
 C23-C16 = C13-C12
 1.46 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5) \\sim Ueq: with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 C9, C11, C19, C1, C5, C2, C4, C3, N3, C20, C18, H20, C8, C12, C6, C10, C13,
 C7, H7A, H7C, C29, N2, H6C, H29B, H29A, C30, C21, C17, H8A, H8B, H8C, H9B, H9C,
  H9A, N1, H6A, H6B, H10A, H10B, H10C, C14, H7B, H30B, H30A, H30C, C22, H21,
 C16, C28, C15, H14, H28B, H22, C23, H15, H28A, H28C, N4, C24, N5, C27, H27A,
 N6, H27B, H27C, N7, C25, H25B, C35, C31, H25A, C26, H26A, H35, C34, C32, H31,
 H26B, H26C, H34, C33, H32, H33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C25(H25A,H25B)
5.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C34(H34), C33(H33), C32(H32), C31(H31), C20(H20), C15(H15),
 C14(H14), C22(H22), C21(H21)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C6(H6A,H6B,H6C), C28(H28A,H28B,H28C), C8(H8A,H8B,H8C),
 C30(H30A,H30B,H30C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C7(H7A,H7B,H7C),
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              17498
_shelx_hkl_checksum              61940
_olex2_submission_special_instructions 'No special instructions were received'