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_7039227
_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         '2(I), 3(C H2 Cl2), C48 H58 N4 O4'
_chemical_formula_sum            'C51 H64 Cl6 I2 N4 O4'
_chemical_formula_weight         1263.56
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-27 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.091(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.1609(13)
_cell_length_b                   32.4937(10)
_cell_length_c                   16.4506(4)
_cell_measurement_reflns_used    8950
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      56.3650
_cell_measurement_theta_min      3.7940
_cell_volume                     12673.8(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(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
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -50.00  35.00   1.00   40.00    --  -40.53  38.00 -30.00   85
  2  \w   -116.00 -14.00   1.00   40.00    --  -40.53 -38.00   0.00  102
  3  \w    -50.00  35.00   1.00   40.00    --  -40.53  38.00-180.00   85
  4  \w     18.00  98.00   1.00   40.00    --   40.53-125.00-120.00   80
  5  \w     37.00  90.00   1.00  125.00    --  115.00 -30.00-120.00   53
  6  \w     41.00 145.00   1.00  125.00    --  115.00 -61.00 120.00  104
  7  \w     37.00  90.00   1.00  125.00    --  115.00 -30.00 150.00   53
  8  \w     87.00 178.00   1.00  125.00    --  115.00  45.00 -30.00   91
  9  \w     40.00  98.00   1.00  125.00    --  115.00 -45.00 -60.00   58
 10  \w     31.00 109.00   1.00  125.00    --  115.00 -94.00-150.00   78
 11  \w    100.00 178.00   1.00  125.00    --  115.00 111.00 -60.00   78
 12  \w     81.00 178.00   1.00  125.00    --  115.00  77.00 -90.00   97
 13  \w   -119.00 -83.00   1.00   40.00    --  -40.53 -77.00 -60.00   36
 14  \w   -116.00 -14.00   1.00   40.00    --  -40.53 -38.00-180.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0025131000
_diffrn_orient_matrix_UB_12      0.0429720000
_diffrn_orient_matrix_UB_13      0.0384211000
_diffrn_orient_matrix_UB_21      0.0629489000
_diffrn_orient_matrix_UB_22      0.0065686000
_diffrn_orient_matrix_UB_23      -0.0020576000
_diffrn_orient_matrix_UB_31      -0.0162026000
_diffrn_orient_matrix_UB_32      0.0188183000
_diffrn_orient_matrix_UB_33      -0.0872869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            77500
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         6.356
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.439
_exptl_absorpt_correction_T_max  0.564
_exptl_absorpt_correction_T_min  0.143
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             5104
_exptl_crystal_recrystallization_method
'Crystals grown from CH2Cl2-heptane at 293 K'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.551
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.100
_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     1265
_refine_ls_number_reflns         22354
_refine_ls_number_restraints     1339
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0843
_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^)+(0.1392P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2352
_refine_ls_wR_factor_ref         0.2691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10744
_reflns_number_total             22354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt01001f2.cif
_cod_data_source_block           0083abc14
_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               7039227
_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. Shared sites
{C154, C254}
3. Restrained distances
 Cl2-C90 \\sim Cl1-C90 \\sim Cl4-C91 \\sim Cl3-C91 \\sim Cl6-C92 \\sim Cl5-C92
\\sim Cl7-C93 \\sim Cl8-C93
 \\sim Cl10-C94 \\sim Cl9-C94 \\sim Cl12-C95A \\sim Cl11-C95A \\sim Cl14-C95B
\\sim Cl13-C95B
 with sigma of 0.01
 O45-C46 \\sim O41-C42 \\sim O49-C50 \\sim O53-C54 \\sim O153-C254 \\sim
O153-C154 \\sim O141-C142 ~
 O149-C150 \\sim O145-C146
 with sigma of 0.01
 C155-C154 \\sim C156-C155 \\sim C255-C254 \\sim C256-C255 \\sim C144-C143
\\sim C142-C143 \\sim C151-
 C150 \\sim C151-C152 \\sim C146-C147 \\sim C148-C147 \\sim C47-C46 \\sim
C47-C48 \\sim C42-C43 \\sim C44-
 C43 \\sim C50-C51 \\sim C52-C51 \\sim C56-C55 \\sim C54-C55
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C154 \\sim C155 \\sim C156 \\sim C254 \\sim C255 \\sim C256: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C154) \\sim Ueq, Uanis(C155) \\sim Ueq, Uanis(C156) \\sim Ueq,
Uanis(C254) \\sim Ueq, Uanis(C255) \\sim Ueq, Uanis(C256) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C154) = Uanis(C254)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C255)=Sof(H25A)=Sof(H25B)=Sof(C254)=Sof(H25C)=Sof(H25D)=Sof(C256)=
 Sof(H25E)=Sof(H25F)=Sof(H25G)=1-FVAR(1)
 Sof(C154)=Sof(H15H)=Sof(H15I)=Sof(C155)=Sof(H15J)=Sof(H15K)=Sof(C156)=
 Sof(H15L)=Sof(H15M)=Sof(H15N)=FVAR(1)
 Sof(Cl14)=Sof(Cl13)=Sof(C95B)=Sof(H95C)=Sof(H95D)=1-FVAR(2)
 Sof(Cl11)=Sof(Cl12)=Sof(C95A)=Sof(H95A)=Sof(H95B)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C95A(H95A,H95B), C93(H93A,H93B), C94(H94A,H94B), C90(H90A,H90B), C91(H91A,
 H91B), C92(H92A,H92B), C119(H11D,H11E), C126(H12A,H12B), C133(H13A,H13B),
 C140(H14A,H14B), C142(H14C,H14D), C143(H14E,H14F), C146(H14J,H14K), C147(H14L,
 H14M), C150(H15A,H15B), C151(H15C,H15D), C154(H15H,H15I), C155(H15J,H15K),
 C19(H19A,H19B), C26(H26A,H26B), C33(H33A,H33B), C40(H40A,H40B), C42(H42A,H42B),
  C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,
 H51B), C54(H54A,H54B), C55(H55A,H55B), C95B(H95C,H95D), C255(H25A,H25B),
 C254(H25C,H25D)
7.b Me refined with riding coordinates:
 C156(H15L,H15M,H15N), C256(H25E,H25F,H25G)
7.c Aromatic/amide H refined with riding coordinates:
 C102(H102), C104(H104), C105(H105), C108(H108), C110(H110), C111(H111),
 C114(H114), C118(H118), C120(H120), C121(H121), C125(H125), C128(H128),
 C132(H132), C134(H134), C135(H135), C139(H139), C2(H2), C4(H4), C5(H5), C8(H8),
  C10(H10), C11(H11), C14(H14), C18(H18), C20(H20), C21(H21), C25(H25),
 C28(H28), C32(H32), C34(H34), C35(H35), C39(H39)
7.d Idealised Me refined as rotating group:
 C106(H10A,H10B,H10C), C112(H11A,H11B,H11C), C144(H14G,H14H,H14I), C148(H14N,
 H14O,H14P), C152(H15E,H15F,H15G), C6(H6A,H6B,H6C), C12(H12C,H12D,H12E),
 C44(H44A,H44B,H44C), C48(H48A,H48B,H48C), C52(H52A,H52B,H52C), C56(H56A,H56B,
 H56C)
;
_shelx_shelxl_version_number     2014/7
_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 2.005
_oxdiff_exptl_absorpt_empirical_full_min 0.540