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_1544701
_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, F6 P, 1.75(C H4 O)'
_chemical_formula_sum            'C81.75 H139 F6 N17 O9.75 P'
_chemical_formula_weight         1661.06
_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                   20.2513(2)
_cell_length_b                   20.7166(3)
_cell_length_c                   21.07611(18)
_cell_measurement_reflns_used    15046
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      72.6030
_cell_measurement_theta_min      3.6880
_cell_volume                     8842.23(17)
_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 0.992
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -90.0000 82

  2 omega   26.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000  150.0000 72

  3 omega   29.00  138.00   1.0000   72.5000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -77.0000 -120.0000 109

  4 omega   94.00  168.00   1.0000   72.5000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000  150.0000 74

  5 omega   17.00  175.00   1.0000   72.5000
omega____ theta____ kappa____ phi______ frames
    -      105.0818    0.0000   30.0000 158
;
_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      0.0685850000
_diffrn_orient_matrix_UB_12      0.0073934000
_diffrn_orient_matrix_UB_13      0.0308268000
_diffrn_orient_matrix_UB_21      -0.0171541000
_diffrn_orient_matrix_UB_22      0.0695940000
_diffrn_orient_matrix_UB_23      0.0194937000
_diffrn_orient_matrix_UB_31      -0.0280215000
_diffrn_orient_matrix_UB_32      -0.0250438000
_diffrn_orient_matrix_UB_33      0.0634084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27726
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.807
_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    1.248
_exptl_crystal_description       plate
_exptl_crystal_F_000             3582
_exptl_crystal_size_max          0.2794
_exptl_crystal_size_mid          0.2509
_exptl_crystal_size_min          0.0706
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 6603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_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     1231
_refine_ls_number_reflns         16875
_refine_ls_number_restraints     2444
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+1.3139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                15770
_reflns_number_total             16875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05058a2.cif
_cod_data_source_block           all-R_cycHC8_TBAPF6
_cod_depositor_comments
'Adding full bibliography for 1544701--1544706.cif.'
_cod_original_cell_volume        8842.22(17)
_cod_database_code               1544701
_chemical_oxdiff_formula         'C80 H132 F6 N17 O8 P1'
_reflns_odcompleteness_completeness 99.10
_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
 H3S-O1A
 1.859 with sigma of 0.01
 H2S-O1C
 1.862 with sigma of 0.01
 H1S-O2S
 1.922 with sigma of 0.01
 C3T-C4T \\sim C7T-C8T \\sim C11T-C12T \\sim C15T-C16T \\sim C3X-C4X \\sim
C7X-C8X \\sim C11X-C12X ~
 C15X-C16X
 with sigma of 0.01
 C1S-O1S \\sim O2S-C2S \\sim O3S-C3S
 with sigma of 0.01
3. Rigid bond restraints
 C5X, C6X, C7X, C8X
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O3S, C3S, O2S, C2S, O1S, C1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
N1T \\sim C1T \\sim C2T \\sim C3T \\sim C4T \\sim C5T \\sim C6T \\sim C7T \\sim
C8T \\sim C9T \\sim C10T \\sim C11T \\sim C12T \\sim C13T \\sim C14T \\sim C15T
\\sim C16T \\sim N1X \\sim C1X \\sim C2X \\sim C3X \\sim C4X \\sim C5X \\sim
C6X \\sim C7X \\sim C8X \\sim C9X \\sim C10X \\sim C11X \\sim C12X \\sim C13X
\\sim C14X \\sim C15X \\sim C16X: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.02
O3S \\sim C3S \\sim O2S \\sim C2S: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C8X) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
5. Rigid body (RIGU) restrains
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C1B, C2B, C3B, C4B, C5B, C6B, C7B,
 C8B, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C, C1D, C2D, C3D, C4D, C5D, C6D, C7D,
  C8D, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8E, C2F, C1F, C6F, C5F, C4F, C3F,
 C7F, C8F, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8G, C1H, C2H, C3H, C4H, C5H, C6H,
  C7H, C8H, C1T, C2T, C3T, C4T, C5T, C6T, C7T, C8T, C9T, C10T, C11T, C12T, C13T,
  C14T, C15T, C16T, C1X, C2X, C3X, C4X, C5X, C6X, C7X, C8X, C9X, C10X, C11X,
 C12X, C13X, C14X, C15X, C16X, C3S, C2S, C1S, N1A, N2A, N1B, N2B, N1C, N2C, N1D,
  N2D, N1E, N2E, N1F, N2F, N1G, N2G, N1H, N2H, N1T, N1X, O1A, O1B, O1C, O1D,
 O1E, O1F, O1G, O1H, O3S, O2S, O1S, F1, F2, F3, F4, F5, F6, P1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{O1F, N2F, N1F, C2F, C1F, C6F, C5F, C4F, C3F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A}
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B}
{O1F, N2F, N1F, C2F, C1F, C6F, C5F, C4F, C3F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1C, N1C, N2C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C}
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D}
{O1F, N2F, N1F, C2F, C1F, C6F, C5F, C4F, C3F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1E, N1E, N2E, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8E}
{O1F, N1F, N2F, C2F, C1F, C6F, C5F, C4F, C3F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1G, N1G, N2G, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8G}
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8H}
{N1T, C1T, C2T, C3T, C4T, C5T, C6T, C7T, C8T, C9T, C10T, C11T, C12T, C13T,
C14T, C15T, C16T} sigma for 1-2: 0.01, 1-3: 0.02
as
{N1X, C1X, C2X, C3X, C4X, C5X, C6X, C7X, C8X, C9X, C10X, C11X, C12X, C13X,
C14X, C15X, C16X}
{O1S, C1S} sigma for 1-2: 0.01, 1-3: 0.02
{O3S, C3S} sigma for 1-2: 0.01, 1-3: 0.02
as
{O2S, C2S}
7. Others
 Sof(O3S)=Sof(H3S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=1-FVAR(1)
 Sof(O2S)=Sof(H2S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(1)
 Sof(N1X)=Sof(C1X)=Sof(H1XA)=Sof(H1XB)=Sof(C2X)=Sof(H2XA)=Sof(H2XB)=Sof(C3X)=
 Sof(H3XA)=Sof(H3XB)=Sof(C4X)=Sof(H4XA)=Sof(H4XB)=Sof(H4XC)=Sof(C5X)=Sof(H5XA)=
 Sof(H5XB)=Sof(C6X)=Sof(H6XA)=Sof(H6XB)=Sof(C7X)=Sof(H7XA)=Sof(H7XB)=Sof(C8X)=
 Sof(H8XA)=Sof(H8XB)=Sof(H8XC)=Sof(C9X)=Sof(H9XA)=Sof(H9XB)=Sof(C10X)=Sof(H10C)=
 Sof(H10D)=Sof(C11X)=Sof(H11C)=Sof(H11D)=Sof(C12X)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C13X)=Sof(H13C)=Sof(H13D)=Sof(C14X)=Sof(H14C)=Sof(H14D)=
 Sof(C15X)=Sof(H15C)=Sof(H15D)=Sof(C16X)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(2)
 Sof(N1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C3T)=
 Sof(H3TA)=Sof(H3TB)=Sof(C4T)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=Sof(C5T)=Sof(H5TA)=
 Sof(H5TB)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(C7T)=Sof(H7TA)=Sof(H7TB)=Sof(C8T)=
 Sof(H8TA)=Sof(H8TB)=Sof(H8TC)=Sof(C9T)=Sof(H9TA)=Sof(H9TB)=Sof(C10T)=Sof(H10A)=
 Sof(H10B)=Sof(C11T)=Sof(H11A)=Sof(H11B)=Sof(C12T)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=Sof(C13T)=Sof(H13A)=Sof(H13B)=Sof(C14T)=Sof(H14A)=Sof(H14B)=
 Sof(C15T)=Sof(H15A)=Sof(H15B)=Sof(C16T)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(2)
 Fixed Sof: O1S(0.75) H1S(0.75) C1S(0.75) H1SA(0.75) H1SB(0.75) H1SC(0.75)
8.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B), C1C(H1C), C2C(H2C), C1D(H1D),
 C2D(H2D), C1E(H1E), C2E(H2E), C2F(H2F), C1F(H1F), C1G(H1G), C2G(H2G), C1H(H1H),
  C2H(H2H)
8.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C8A(H8AA,
 H8AB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB),
 C8B(H8BA,H8BB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C6C(H6CA,H6CB),
  C8C(H8CA,H8CB), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C6D(H6DA,
 H6DB), C8D(H8DA,H8DB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB),
 C6E(H6EA,H6EB), C8E(H8EA,H8EB), C6F(H6FA,H6FB), C5F(H5FA,H5FB), C4F(H4FA,H4FB),
  C3F(H3FA,H3FB), C8F(H8FA,H8FB), C3G(H3GA,H3GB), C4G(H4GA,H4GB), C5G(H5GA,
 H5GB), C6G(H6GA,H6GB), C8G(H8GA,H8GB), C3H(H3HA,H3HB), C4H(H4HA,H4HB),
 C5H(H5HA,H5HB), C6H(H6HA,H6HB), 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), C1X(H1XA,H1XB), C2X(H2XA,H2XB), C3X(H3XA,H3XB), C5X(H5XA,
 H5XB), C6X(H6XA,H6XB), C7X(H7XA,H7XB), C9X(H9XA,H9XB), C10X(H10C,H10D),
 C11X(H11C,H11D), C13X(H13C,H13D), C14X(H14C,H14D), C15X(H15C,H15D)
8.c Tetrahedral OH refined with riding coordinates:
 O3S(H3S)
8.d Idealised Me refined as rotating group:
 C4T(H4TA,H4TB,H4TC), C8T(H8TA,H8TB,H8TC), C12T(H12A,H12B,H12C), C16T(H16A,
 H16B,H16C), C4X(H4XA,H4XB,H4XC), C8X(H8XA,H8XB,H8XC), C12X(H12D,H12E,H12F),
 C16X(H16D,H16E,H16F), C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,H2SC), C1S(H1SA,H1SB,
 H1SC)
8.e Idealised tetrahedral OH refined as rotating group:
 O2S(H2S), O1S(H1S)
;
_shelx_res_checksum              16319
_shelx_hkl_checksum              63543
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'MiTeGen 0.2 mm'
_olex2_submission_special_instructions 'No special instructions were received'