Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution
Kaabel, Sandra; Adamson, Jasper; Topić, Filip; Kiesilä, Anniina; Kalenius, Elina; Öeren, Mario; Reimund, Mart; Prigorchenko, Elena; Lõokene, Aivar; Reich, Hans J.; Rissanen, Kari; Aav, Riina; Chem. Sci. 8 (2017) 2184–; doi:10.1039/C6SC05058A

data_1544704
_publ_section_title
;
 Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size,
 shape and charge distribution
;
_journal_issue                   3
_journal_name_full               'Chem. Sci.'
_journal_page_first              2184
_journal_paper_doi               10.1039/C6SC05058A
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C64 H96 N16 O8, C16 H36 N, 1.75(C H4 O), O4 Re'
_chemical_formula_sum            'C81.75 H139 N17 O13.75 Re'
_chemical_formula_weight         1766.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-03 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1641(3)
_cell_length_b                   20.8019(3)
_cell_length_c                   21.1254(3)
_cell_measurement_reflns_used    20651
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.0330
_cell_measurement_theta_min      4.2490
_cell_volume                     8861.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
Mercury CSD 3.3 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega -115.00  -22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000  120.0000 93

  2 omega  -93.00  -18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000 -180.0000 75

  3 omega  -18.00   17.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 35

  4 omega  -36.00  -10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -30.0000 26

  5 omega   43.00   74.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000    0.0000 31

  6 omega  103.00  129.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000  -60.0000 26

  7 omega   79.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -180.0000 99

  8 omega   40.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000   30.0000 26

  9 omega   48.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -45.0000  -90.0000 46

 10 omega  142.00  169.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000  -60.0000 27

 11 omega   33.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -90.0000 64

 12 omega   30.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000   60.0000 38

 13 omega   54.00  122.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000   60.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0147071000
_diffrn_orient_matrix_UB_12      -0.0313897000
_diffrn_orient_matrix_UB_13      0.0646023000
_diffrn_orient_matrix_UB_21      0.0749052000
_diffrn_orient_matrix_UB_22      0.0030898000
_diffrn_orient_matrix_UB_23      -0.0140807000
_diffrn_orient_matrix_UB_31      0.0034120000
_diffrn_orient_matrix_UB_32      0.0669537000
_diffrn_orient_matrix_UB_33      0.0308500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         74.330
_diffrn_reflns_theta_min         3.030
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.239
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_density_diffrn    1.324
_exptl_crystal_description       prism
_exptl_crystal_F_000             3734
_exptl_crystal_size_max          0.2767
_exptl_crystal_size_mid          0.2026
_exptl_crystal_size_min          0.1869
_refine_diff_density_max         1.422
_refine_diff_density_min         -2.077
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 6924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1102
_refine_ls_number_reflns         17494
_refine_ls_number_restraints     1991
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0901P)^2^+11.1218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                16831
_reflns_number_total             17494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05058a2.cif
_cod_data_source_block           all-R_cycHC8_TBAReO4
_cod_depositor_comments
'Adding full bibliography for 1544701--1544706.cif.'
_cod_database_code               1544704
_chemical_oxdiff_formula         'C80 H132 N17 O12 Re'
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H2S-O1A
 1.856 with sigma of 0.02
 O1I-O2I \\sim O1I-O3I \\sim O1I-O4I \\sim O2I-O3I \\sim O2I-O4I \\sim O3I-O4I
 with sigma of 0.02
 Re1I-O1I \\sim Re1I-O2I \\sim Re1I-O3I \\sim Re1I-O4I
 with sigma of 0.01
 O1K-O2K \\sim O1K-O3K \\sim O1K-O4K \\sim O2K-O3K \\sim O2K-O4K \\sim O3K-O4K
 with sigma of 0.02
 Re1K-O1K \\sim Re1K-O2K \\sim Re1K-O3K \\sim Re1K-O4K
 with sigma of 0.01
 C7T-C8T \\sim C3T-C4T \\sim C11T-C12T \\sim C15T-C16T
 with sigma of 0.02
 O1S-C1S \\sim O2S-C2S \\sim C1SB-O1SB
 with sigma of 0.01
3. Rigid bond restraints
 O1S, C1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2S, C2S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Re1I \\sim O1I \\sim O2I \\sim O3I \\sim O4I \\sim Re1K \\sim O1K \\sim O2K
\\sim O3K \\sim O4K: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.02
O1SB \\sim C1SB \\sim O1S \\sim C1S: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(O2S) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(O1S) \\sim Ueq, Uanis(C1S)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8B, C2H, C1H, C6H, C5H, C4H, C3H, C7H,
 C8A, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8C, C1C, C2C, C3C, C4C, C5C, C6C, C7C,
  C8D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8E, C1E, C2E, C3E, C4E, C5E, C6E,
 C7E, C8F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8G, C1G, C2G, C3G, C4G, C5G, C6G,
  C7G, C8H, C1T, C2T, C3T, C4T, C5T, C6T, C7T, C8T, C9T, C10T, C11T, C12T, C13T,
  C14T, C15T, C16T, C1SB, C1S, C2S, O1A, O1H, O1B, O1C, O1D, O1E, O1F, O1G,
 O1SB, O1S, O2S, O1I, O2I, O3I, O4I, O1K, O2K, O3K, O4K, N1A, N2A, N2H, N1H,
 N1B, N2B, N1C, N2C, N1D, N2D, N1E, N2E, N1F, N2F, N1G, N2G, N1T, Re1I, Re1K
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{O1H, N2H, N1H, C2H, C1H, C6H, C5H, C4H, C3H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8B}
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8C}
{O1H, N2H, N1H, C2H, C1H, C6H, C5H, C4H, C3H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1C, N1C, N2C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8D}
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8E}
{O1H, N2H, N1H, C2H, C1H, C6H, C5H, C4H, C3H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1E, N1E, N2E, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8F}
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8G}
{O1H, N2H, N1H, C2H, C1H, C6H, C5H, C4H, C3H, C7H, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1G, N1G, N2G, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8H}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.02
as
{C5T, C6T, C7T, C8T}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.02
as
{C9T, C10T, C11T, C12T}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.02
as
{C13T, C14T, C15T, C16T}
7. Others
 Sof(Re1K)=Sof(O1K)=Sof(O2K)=Sof(O3K)=Sof(O4K)=1-FVAR(1)
 Sof(Re1I)=Sof(O1I)=Sof(O2I)=Sof(O3I)=Sof(O4I)=FVAR(1)
 Sof(O1SB)=Sof(H1SB)=Sof(C1SB)=Sof(H1SA)=Sof(H1SC)=Sof(H1SD)=1-FVAR(2)
 Sof(O1S)=Sof(H1S)=Sof(C1S)=Sof(H1SE)=Sof(H1SF)=Sof(H1SG)=FVAR(2)
 Fixed Sof: O2S(0.75) H2S(0.75) C2S(0.75) H2SA(0.75) H2SB(0.75) H2SC(0.75)
8.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C2H(H2H), C1H(H1H), C1B(H1B), C2B(H2B), C1C(H1C),
 C2C(H2C), C1D(H1D), C2D(H2D), C1E(H1E), C2E(H2E), C1F(H1F), C2F(H2F), C1G(H1G),
  C2G(H2G)
8.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C8B(H8BA,
 H8BB), C6H(H6HA,H6HB), C5H(H5HA,H5HB), C4H(H4HA,H4HB), C3H(H3HA,H3HB),
 C8A(H8AA,H8AB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB),
  C8C(H8CA,H8CB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C6C(H6CA,
 H6CB), C8D(H8DA,H8DB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB),
 C6D(H6DA,H6DB), C8E(H8EA,H8EB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB),
  C6E(H6EA,H6EB), C8F(H8FA,H8FB), C3F(H3FA,H3FB), C4F(H4FA,H4FB), C5F(H5FA,
 H5FB), C6F(H6FA,H6FB), C8G(H8GA,H8GB), C3G(H3GA,H3GB), C4G(H4GA,H4GB),
 C5G(H5GA,H5GB), C6G(H6GA,H6GB), C8H(H8HA,H8HB), C1T(H1TA,H1TB), C2T(H2TA,H2TB),
  C3T(H3TA,H3TB), C5T(H5TA,H5TB), C6T(H6TA,H6TB), C7T(H7TA,H7TB), C9T(H9TA,
 H9TB), C10T(H10A,H10B), C11T(H11A,H11B), C13T(H13A,H13B), C14T(H14A,H14B),
 C15T(H15A,H15B)
8.c Idealised Me refined as rotating group:
 C4T(H4TA,H4TB,H4TC), C8T(H8TA,H8TB,H8TC), C12T(H12A,H12B,H12C), C16T(H16A,
 H16B,H16C), C1SB(H1SA,H1SC,H1SD), C1S(H1SE,H1SF,H1SG), C2S(H2SA,H2SB,H2SC)
8.d Idealised tetrahedral OH refined as rotating group:
 O1SB(H1SB), O1S(H1S), O2S(H2S)
;
_shelx_res_checksum              25298
_shelx_hkl_checksum              26147
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'