Coordination chemistry of a calix[4]arene-based NHC ligand: dinuclear complexes and comparison to I(i)Pr2Me2.
Patchett, Ruth; Chaplin, Adrian B.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 8945–8955; doi:10.1039/c6dt01001f

data_7039230
_publ_section_title
;
 Coordination chemistry of a calix[4]arene-based NHC ligand: dinuclear
 complexes and comparison to I(i)Pr2Me2.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8945
_journal_page_last               8955
_journal_paper_doi               10.1039/c6dt01001f
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C48 H56 Ag N4 O4, C32 H12 B F24'
_chemical_formula_sum            'C80 H68 Ag B F24 N4 O4'
_chemical_formula_weight         1724.06
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                85.952(3)
_cell_angle_beta                 77.095(5)
_cell_angle_gamma                80.605(5)
_cell_formula_units_Z            2
_cell_length_a                   11.5261(8)
_cell_length_b                   19.1677(9)
_cell_length_c                   20.4328(7)
_cell_measurement_reflns_used    7782
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      25.4370
_cell_measurement_theta_min      3.7790
_cell_volume                     4338.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -24.00    2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3716  -99.0000   90.0000 26

  2 omega  -61.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4341  -19.0000  -60.0000 103

  3 omega   34.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4341   38.0000  -30.0000 36

  4 omega  -16.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3716  -99.0000  -60.0000 40

  5 omega    3.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4341   38.0000  120.0000 80

  6 omega   42.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4341  178.0000  -30.0000 63

  7 omega -105.00  -61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3716 -178.0000   60.0000 44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0468444000
_diffrn_orient_matrix_UB_12      -0.0288386000
_diffrn_orient_matrix_UB_13      0.0009307000
_diffrn_orient_matrix_UB_21      0.0385936000
_diffrn_orient_matrix_UB_22      0.0237578000
_diffrn_orient_matrix_UB_23      0.0043996000
_diffrn_orient_matrix_UB_31      -0.0198947000
_diffrn_orient_matrix_UB_32      -0.0035405000
_diffrn_orient_matrix_UB_33      0.0353509000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38190
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.682
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
)
TITL 0096abc14
CELL   11.5261   19.1677   20.4328     85.95     77.10     80.61
SPGR P-1
C101 0.329 0.328 0.974 !       1.60 eA-3
C102 0.324 0.314 0.902 !       1.46 eA-3
Q103 0.154 0.062 0.526 !       1.37 eA-3
C104 0.465 0.707 0.218 !       1.35 eA-3
Q105 0.937 0.828 0.694 !       1.31 eA-3
C106 0.505 0.327 0.768 !       1.17 eA-3
C107 0.407 0.313 0.832 !       1.00 eA-3
C108 0.466 0.325 0.817 !       0.96 eA-3
Q109 0.096 0.870 0.435 !       0.87 eA-3
Q110 0.358 0.497 0.032 !       0.80 eA-3
Q111 0.765 1.003 0.503 !       0.68 eA-3
C112 0.455 0.358 0.789 !       0.65 eA-3
Q113 0.235 0.484 0.675 !       0.61 eA-3
Q114 0.800 0.956 0.510 !       0.60 eA-3
Q115 0.637 0.388 0.576 !       0.60 eA-3
Q116 0.626 0.577 0.875 !       0.57 eA-3
Q117 0.065 0.637 0.194 !       0.57 eA-3
Q118 0.829 0.472 0.599 !       0.56 eA-3
Q119 0.032 0.886 0.620 !       0.55 eA-3
Q120 0.845 0.143 0.185 !       0.53 eA-3
Q121 0.842 0.537 0.409 !       0.53 eA-3
Q122 0.953 0.176 0.332 !       0.51 eA-3
Q123 0.265 0.877 0.982 !       0.51 eA-3
Q124 0.297 0.864 0.379 !       0.50 eA-3
Q125 0.779 0.498 0.353 !       0.50 eA-3
Q126 0.752 0.653 0.718 !       0.50 eA-3
)
;
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1269
_refine_ls_number_reflns         16436
_refine_ls_number_restraints     883
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10036
_reflns_number_total             16436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt01001f2.cif
_cod_data_source_block           0096abc14a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7039227--7039236.cif.
;
_cod_database_code               7039230
_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
 C207-F1 \\sim C207-F2 \\sim C207-F3 \\sim C207-F1A \\sim C207-F2A \\sim
C207-F3A
 with sigma of 0.01
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.01
 C203-F1 \\sim C203-F2 \\sim C203-F3 \\sim C203-F1A \\sim C203-F2A \\sim
C203-F3A
 with sigma of 0.01
 C208-F4 \\sim C208-F5 \\sim C208-F6 \\sim C208-F4A \\sim C208-F5A \\sim
C208-F6A
 with sigma of 0.01
 F4-F5 \\sim F5-F6 \\sim F6-F4 \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.01
 C205-F4 \\sim C205-F5 \\sim C205-F6 \\sim C205-F4A \\sim C205-F5A \\sim
C205-F6A
 with sigma of 0.01
 C215-F7 \\sim C215-F8 \\sim C215-F9 \\sim C215-F7A \\sim C215-F8A \\sim
C215-F9A
 with sigma of 0.01
 F7-F8 \\sim F8-F9 \\sim F9-F7 \\sim F7A-F8A \\sim F8A-F9A \\sim F9A-F7A
 with sigma of 0.01
 C211-F7 \\sim C211-F8 \\sim C211-F9 \\sim C211-F7A \\sim C211-F8A \\sim
C211-F9A
 with sigma of 0.01
 C216-F10 \\sim C216-F11 \\sim C216-F12 \\sim C216-F10A \\sim C216-F11A \\sim
C216-F12A
 with sigma of 0.01
 F10-F11 \\sim F11-F12 \\sim F12-F10 \\sim F10A-F11A \\sim F11A-F12A \\sim
F12A-F10A
 with sigma of 0.01
 C213-F10 \\sim C213-F11 \\sim C213-F12 \\sim C213-F10A \\sim C213-F11A \\sim
C213-F12A
 with sigma of 0.01
 C223-F13 \\sim C223-F14 \\sim C223-F15 \\sim C223-F13A \\sim C223-F14A \\sim
C223-F15A
 with sigma of 0.01
 F13-F14 \\sim F14-F15 \\sim F15-F13 \\sim F13A-F14A \\sim F14A-F15A \\sim
F15A-F13A
 with sigma of 0.01
 C219-F13 \\sim C219-F14 \\sim C219-F15 \\sim C219-F13A \\sim C219-F14A \\sim
C219-F15A
 with sigma of 0.01
 C224-F16 \\sim C224-F17 \\sim C224-F18 \\sim C224-F16A \\sim C224-F17A \\sim
C224-F18A
 with sigma of 0.01
 F16-F17 \\sim F17-F18 \\sim F18-F16 \\sim F16A-F17A \\sim F17A-F18A \\sim
F18A-F16A
 with sigma of 0.01
 C221-F16 \\sim C221-F17 \\sim C221-F18 \\sim C221-F16A \\sim C221-F17A \\sim
C221-F18A
 with sigma of 0.01
 C231-F19 \\sim C231-F20 \\sim C231-F21 \\sim C231-F19A \\sim C231-F20A \\sim
C231-F21A
 with sigma of 0.01
 F19-F20 \\sim F20-F21 \\sim F21-F19 \\sim F19A-F20A \\sim F20A-F21A \\sim
F21A-F19A
 with sigma of 0.01
 C227-F19 \\sim C227-F20 \\sim C227-F21 \\sim C227-F19A \\sim C227-F20A \\sim
C227-F21A
 with sigma of 0.01
 O50-C51A \\sim O50-C51 \\sim O54-C55A \\sim O54-C55 \\sim O46-C47A \\sim
O46-C47 \\sim O42-C43 \\sim O42-
 C43A
 with sigma of 0.01
 C52A-C51A \\sim C51-C52 \\sim C52-C53 \\sim C53A-C52A \\sim C56A-C55A \\sim
C56-C55 \\sim C57-C56 ~
 C57A-C56A \\sim C49A-C48 \\sim C49-C48A \\sim C48A-C47A \\sim C48-C47 \\sim
C44A-C43A \\sim C43-C44 ~
 C45-C44 \\sim C44A-C45A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O46) \\sim Ueq, Uanis(O50) \\sim Ueq, Uanis(O54) \\sim Ueq, Uanis(O42)
\\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C47A) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(C55A) \\sim Ueq, Uanis(C52A) \\sim Ueq, Uanis(C48A)
\\sim Ueq, Uanis(C56A) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C57A) \\sim Ueq,
Uanis(C45) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56)
\\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(C49A) \\sim Ueq, Uanis(C43A) \\sim Ueq, Uanis(C44A) \\sim Ueq,
Uanis(C45A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq,
Uanis(F4) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A)
\\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F7) \\sim Ueq,
Uanis(F7A) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F9)
\\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F10A) \\sim Ueq,
Uanis(F11) \\sim Ueq, Uanis(F11A) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F12A)
\\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F14) \\sim Ueq,
Uanis(F14A) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F15A) \\sim Ueq, Uanis(F16)
\\sim Ueq, Uanis(F16A) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F17A) \\sim Ueq,
Uanis(F18) \\sim Ueq, Uanis(F18A) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F19A)
\\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F20A) \\sim Ueq, Uanis(F21) \\sim Ueq,
Uanis(F21A) \\sim Ueq, Uanis(F22) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F24)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C43A) = Uanis(C43)
Uanis(C44A) = Uanis(C44)
Uanis(C45A) = Uanis(C45)
Uanis(C47A) = Uanis(C47)
Uanis(C49) = Uanis(C49A)
Uanis(C55A) = Uanis(C55)
Uanis(C56) = Uanis(C56A)
Uanis(C57) = Uanis(C57A)
Uanis(C51A) = Uanis(C51)
Uanis(C52A) = Uanis(C52)
Uanis(C53A) = Uanis(C53)
Uanis(C48) = Uanis(C48A)
4. Others
 Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C56A)=Sof(H56C)=Sof(H56D)=Sof(C57A)=
 Sof(H57D)=Sof(H57E)=Sof(H57F)=1-FVAR(1)
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(C57)=Sof(H57A)=
 Sof(H57B)=Sof(H57C)=FVAR(1)
 Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49)=
 Sof(H49A)=Sof(H49B)=Sof(H49C)=1-FVAR(2)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49A)=Sof(H49D)=
 Sof(H49E)=Sof(H49F)=FVAR(2)
 Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52C)=Sof(H52D)=Sof(C53A)=
 Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(3)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=
 Sof(H53B)=Sof(H53C)=FVAR(3)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(4)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(4)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(5)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(5)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(6)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(6)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(7)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(7)
 Fixed Sof: C43(0.5) H43A(0.5) H43B(0.5) C43A(0.5) H43C(0.5) H43D(0.5)
 C44(0.5) H44A(0.5) H44B(0.5) C44A(0.5) H44C(0.5) H44D(0.5) C45(0.5) H45A(0.5)
 H45B(0.5) H45C(0.5) C45A(0.5) H45D(0.5) H45E(0.5) H45F(0.5) F10(0.5) F10A(0.5)
 F11(0.5) F11A(0.5) F12(0.5) F12A(0.5) F16(0.5) F16A(0.5) F17(0.5) F17A(0.5)
 F18(0.5) F18A(0.5) F19(0.5) F19A(0.5) F20(0.5) F20A(0.5) F21(0.5) F21A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C27(H27A,H27B), C34(H34A,H34B), C41(H41A,H41B), C43(H43A,
 H43B), C43A(H43C,H43D), C44(H44A,H44B), C44A(H44C,H44D), C47(H47A,H47B),
 C47A(H47C,H47D), C48(H48A,H48B), C48A(H48C,H48D), C51(H51A,H51B), C51A(H51C,
 H51D), C52(H52A,H52B), C52A(H52C,H52D), C55(H55A,H55B), C55A(H55C,H55D),
 C56(H56A,H56B), C56A(H56C,H56D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C15(H15), C19(H19), C21(H21), C22(H22),
 C26(H26), C29(H29), C33(H33), C35(H35), C36(H36), C40(H40), C202(H202),
 C204(H204), C206(H206), C210(H210), C212(H212), C214(H214), C218(H218),
 C220(H220), C222(H222), C226(H226), C228(H228), C230(H230)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C45(H45A,H45B,H45C), C45A(H45D,H45E,
 H45F), C49(H49A,H49B,H49C), C49A(H49D,H49E,H49F), C53(H53A,H53B,H53C),
 C53A(H53D,H53E,H53F), C57(H57A,H57B,H57C), C57A(H57D,H57E,H57F)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'