On the mercuration, palladation, transmetalation and direct auration of a C^N^C pincer ligand.
McEllin, Alice Jane; Goult, Christopher A.; Whitwood, Adrian C.; Lynam, Jason M.; Bruce, Duncan W.; Dalton transactions (Cambridge, England : 2003) 52 (2023) 872–876; doi:10.1039/d2dt04114f

data_7712107
_publ_section_title
;
 On the mercuration, palladation, transmetalation and direct auration of a
 C^N^C pincer ligand.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              872
_journal_page_last               876
_journal_paper_doi               10.1039/d2dt04114f
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         '1(C33 H43 Cl2 Hg2 N O4)'
_chemical_formula_sum            'C33 H43 Cl2 Hg2 N O4'
_chemical_formula_weight         989.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2022-08-05 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.177(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0415(6)
_cell_length_b                   18.4352(7)
_cell_length_c                   27.0890(9)
_cell_measurement_reflns_used    8797
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.7970
_cell_measurement_theta_min      4.7080
_cell_volume                     6798.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     12.00  42.00   1.00    3.00    --    0.00  77.00-120.00   30
  2  \w    -17.00  16.00   1.00    3.00    --    0.00 -77.00  30.00   33
  3  \w    -13.00  15.00   1.00    3.00    --    0.00 -77.00-150.00   28
  4  \w    -28.00   7.00   1.00    3.00    --    0.00  77.00-120.00   35
  5  \w     42.00  86.00   1.00   12.00    --   54.00  57.00-180.00   44
  6  \w     52.00 111.00   1.00   12.00    --   54.00-125.00  90.00   59
  7  \w     34.00 123.00   1.00   12.00    --   54.00  57.00  60.00   89
  8  \w     41.00  81.00   1.00   12.00    --   54.00  57.00-120.00   40
  9  \w    -15.00  74.00   1.00   12.00    --   54.00 -57.00 -90.00   89
 10  \w     80.00 107.00   1.00   12.00    --  108.00-111.00-150.00   27
 11  \w     41.00 121.00   1.00   12.00    --  108.00 -63.00 150.00   80
 12  \w     71.00 107.00   1.00   12.00    --  108.00 -91.00 -30.00   36
 13  \w     54.00  87.00   1.00   12.00    --  108.00 -91.00  60.00   33
 14  \w    138.00 173.00   1.00   12.00    --  108.00  77.00-150.00   35
 15  \w     37.00 101.00   1.00   12.00    --  108.00-111.00 -60.00   64
 16  \w    124.00 150.00   1.00   12.00    --  108.00 111.00 -60.00   26
 17  \w     77.00 174.00   1.00   12.00    --  108.00  25.00  60.00   97
 18  \w    102.00 174.00   1.00   12.00    --  108.00  50.00 -60.00   72
 19  \w     44.00 105.00   1.00   12.00    --  108.00 -91.00 120.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150793000
_diffrn_orient_matrix_UB_12      -0.0804865000
_diffrn_orient_matrix_UB_13      0.0150751000
_diffrn_orient_matrix_UB_21      0.1047698000
_diffrn_orient_matrix_UB_22      0.0028792000
_diffrn_orient_matrix_UB_23      -0.0080088000
_diffrn_orient_matrix_UB_31      0.0399525000
_diffrn_orient_matrix_UB_32      0.0220521000
_diffrn_orient_matrix_UB_33      0.0561944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.995
_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       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25928
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.037
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.705
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       plate
_exptl_crystal_F_000             3792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform and methanol'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.02
_refine_diff_density_max         4.094
_refine_diff_density_min         -3.265
_refine_diff_density_rms         0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         12081
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0490P)^2^+129.9697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9956
_reflns_number_total             12081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt04114f2.cif
_cod_data_source_block           dwb2014
_cod_depositor_comments
'Adding full bibliography for 7712105--7712107.cif.'
_cod_original_cell_volume        6798.7(5)
_cod_database_code               7712107
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H43 Cl2 Hg2 N1 O4'
_chemical_oxdiff_usercomment     'Alice Jane McEllin AJM150'
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.092
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C60-C59 = C60A-C59 = C60-C61 = C62-C61 = C61A-C60A = C61A-C62A
 1.52 with sigma of 0.01
 C51-C52 = C52A-C51A = C53-C52 = C52A-C53A = C53-C54 = C54A-C53A
 1.52 with sigma of 0.01
 C18-C19 = C18-C19A = C20-C19 = C20A-C19A = C20-C21 = C20A-C21A
 1.51 with sigma of 0.01
 C27-C26 = C26-C27A = C27-C28 = C27A-C28A = C28A-C29A = C28-C29
 1.52 with sigma of 0.01
 C63A-C64A = C64-C63 = C65A-C64A = C64-C65 = C65A-C66A = C66-C65
 1.52 with sigma of 0.01
 O8A-C63A = O8-C63
 1.41 with sigma of 0.01
 C51-C53 = C52-C54
 2.49 with sigma of 0.01
 C27A-C29A
 2.49 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C52A) \\sim Ueq, Uanis(C52) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C51A) \\sim Ueq, Uanis(C51) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O8A) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(C63A) \\sim Ueq, Uanis(C63)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C27A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C28)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C19) = Uanis(C19A)
Uanis(C27A) = Uanis(C27)
Uanis(C53) = Uanis(C53A)
Uanis(C28A) = Uanis(C28)
Uanis(C51) = Uanis(C51A)
Uanis(C60) = Uanis(C60A)
Uanis(C62A) = Uanis(C62)
Uanis(C61A) = Uanis(C61)
Uanis(C64A) = Uanis(C64)
4. Others
 Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=
 Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
 Sof(C63A)=Sof(H63C)=Sof(H63D)=Sof(C64A)=Sof(H64C)=Sof(H64D)=Sof(C65A)=
 Sof(H65C)=Sof(H65D)=Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(O8A)=1-FVAR(2)
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(C65)=Sof(H65A)=
 Sof(H65B)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(O8)=FVAR(2)
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28C)=
 Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(3)
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(3)
 Sof(H59C)=Sof(H59D)=Sof(C60A)=Sof(H60C)=Sof(H60D)=Sof(C61A)=Sof(H61C)=
 Sof(H61D)=Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=1-FVAR(4)
 Sof(H59A)=Sof(H59B)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(4)
 Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=Sof(C53A)=
 Sof(H53C)=Sof(H53D)=Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(5)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=
 Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(5)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18(H18C,H18D), C19(H19A,H19B), C19A(H19C,H19D), C20(H20A,
 H20B), C20A(H20C,H20D), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C26(H26A,H26B), C26(H26C,H26D), C27(H27A,H27B), C27A(H27C,H27D), C28(H28A,
 H28B), C28A(H28C,H28D), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B),
 C51(H51A,H51B), C51A(H51C,H51D), C52(H52A,H52B), C52A(H52C,H52D), C53(H53A,
 H53B), C53A(H53C,H53D), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B),
 C59(H59C,H59D), C59(H59A,H59B), C60(H60A,H60B), C60A(H60C,H60D), C61(H61A,
 H61B), C61A(H61C,H61D), C63(H63A,H63B), C63A(H63C,H63D), C64(H64A,H64B),
 C64A(H64C,H64D), C65(H65A,H65B), C65A(H65C,H65D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C35(H35),
 C36(H36), C41(H41), C42(H42), C43(H43), C48(H48), C49(H49)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F), C25(H25A,H25B,H25C), C29(H29A,H29B,
 H29C), C29A(H29D,H29E,H29F), C33(H33A,H33B,H33C), C54(H54A,H54B,H54C),
 C54A(H54D,H54E,H54F), C58(H58A,H58B,H58C), C62(H62A,H62B,H62C), C62A(H62D,H62E,
 H62F), C66(H66A,H66B,H66C), C66A(H66D,H66E,H66F)
;
_shelx_res_checksum              4736
_shelx_hkl_checksum              16265
_olex2_date_sample_data_collection 2020-06-22
_olex2_date_sample_submission    2020-06-17
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id AJM150
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.682