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_1544702
_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 P, F6 Sb, 2(C H4 O)'
_chemical_formula_sum            'C82 H140 F6 N16 O10 P Sb'
_chemical_formula_weight         1776.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-16
_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                 90.0578(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.20836(17)
_cell_length_b                   21.3780(2)
_cell_length_c                   20.70075(19)
_cell_measurement_reflns_used    49996
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.1330
_cell_measurement_theta_min      4.3360
_cell_volume                     8943.02(14)
_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      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -115.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000 -180.0000 101

  2 omega -115.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  -30.0000 101

  3 omega -116.00  -18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000   60.0000 98

  4 omega  -34.00   74.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -77.0000  -90.0000 108

  5 omega   81.00  178.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   45.0000   60.0000 97

  6 omega   74.00  178.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000    0.0000 104

  7 omega   78.00  164.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -60.0000 86

  8 omega   78.00  104.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   30.0000 26

  9 omega   37.00  106.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -90.0000 69

 10 omega   94.00  163.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000 -120.0000 69

 11 omega  117.00  176.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 59

 12 omega   97.00  168.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000  120.0000 71

 13 omega   74.00  100.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 26

 14 omega   33.00  107.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -180.0000 74

 15 omega   37.00   91.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000 -120.0000 54

 16 omega   78.00  113.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 35

 17 omega   77.00  103.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000  -39.8282 26
;
_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      -0.0555433000
_diffrn_orient_matrix_UB_12      -0.0286074000
_diffrn_orient_matrix_UB_13      -0.0416283000
_diffrn_orient_matrix_UB_21      -0.0348291000
_diffrn_orient_matrix_UB_22      0.0640651000
_diffrn_orient_matrix_UB_23      -0.0025750000
_diffrn_orient_matrix_UB_31      0.0388635000
_diffrn_orient_matrix_UB_32      0.0165796000
_diffrn_orient_matrix_UB_33      -0.0616194000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            66781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         74.306
_diffrn_reflns_theta_min         2.972
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.249
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_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)
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            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             3776
_exptl_crystal_size_max          0.1754
_exptl_crystal_size_mid          0.1528
_exptl_crystal_size_min          0.1056
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 15010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0114(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2106
_refine_ls_number_reflns         33880
_refine_ls_number_restraints     3641
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0552P)^2^+3.1795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                33696
_reflns_number_total             33880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05058a2.cif
_cod_data_source_block           all-R_cycHC8_TBPSbF6
_cod_depositor_comments
'Adding full bibliography for 1544701--1544706.cif.'
_cod_original_cell_volume        8943.00(14)
_cod_database_code               1544702
_chemical_oxdiff_formula         'C82 H140 N16 O10 P Sb F6'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7944(6) 0.2056(6)
2. 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
3. Restrained distances
 O1S-C1S \\sim O2S-C2S \\sim O3S-C3S \\sim O4S-C4S
 with sigma of 0.01
4. 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, C2D, C1D, C6D, C5D, C4D, C3D, C7D,
  C8D, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8E, C1F, C2F, C3F, C4F, C5F, C6F,
 C7F, C8F, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8G, C1H, C2H, C3H, C4H, C5H, C6H,
  C7H, C8H, C1I, C2I, C3I, C4I, C5I, C6I, C7I, C8I, C1J, C2J, C3J, C4J, C5J,
 C6J, C7J, C8J, C1K, C2K, C3K, C4K, C5K, C6K, C7K, C8K, C1L, C2L, C3L, C4L, C5L,
  C6L, C7L, C8L, C1M, C2M, C3M, C4M, C5M, C6M, C7M, C8M, C1N, C2N, C3N, C4N,
 C5N, C6N, C7N, C8N, C1O, C2O, C3O, C4O, C5O, C6O, C7O, C8O, C2P, C1P, C6P, C5P,
  C4P, C3P, C7P, C8P, 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, C2S, C1S, C3S, C4S, N1A, N2A, N1B,
 N2B, N1C, N2C, N2D, N1D, N1E, N2E, N1F, N2F, N1G, N2G, N1H, N2H, N1I, N2I, N1J,
  N2J, N1K, N2K, N1L, N2L, N1M, N2M, N1N, N2N, N1O, N2O, N2P, N1P, O1A, O1B,
 O1C, O1D, O1E, O1F, O1G, O1H, O1I, O1J, O1K, O1L, O1M, O1N, O1O, O1P, O2S, O1S,
  O3S, O4S, F1A, F2A, F3A, F4A, F5A, F6A, F1B, F2B, F3B, F4B, F5B, F6B, P1T,
 P1X, Sb1, Sb2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1D, N2D, N1D, C2D, C1D, C6D, C5D, C4D, C3D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A}
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B}
{O1D, N2D, N1D, C2D, C1D, C6D, C5D, C4D, C3D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1C, N1C, N2C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C}
{O1D, N2D, N1D, C2D, C1D, C6D, C5D, C4D, C3D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1E, N1E, N2E, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8E}
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F}
{O1D, N2D, N1D, C2D, C1D, C6D, C5D, C4D, C3D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1G, N1G, N2G, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8G}
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8H}
{O1P, N2P, N1P, C2P, C1P, C6P, C5P, C4P, C3P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1I, N1I, N2I, C1I, C2I, C3I, C4I, C5I, C6I, C7I, C8I}
{O1P, N1P, N2P, C1P, C2P, C3P, C4P, C5P, C6P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1J, N1J, N2J, C1J, C2J, C3J, C4J, C5J, C6J, C7J, C8J}
{O1P, N2P, N1P, C2P, C1P, C6P, C5P, C4P, C3P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1K, N1K, N2K, C1K, C2K, C3K, C4K, C5K, C6K, C7K, C8K}
{O1P, N1P, N2P, C1P, C2P, C3P, C4P, C5P, C6P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1L, N1L, N2L, C1L, C2L, C3L, C4L, C5L, C6L, C7L, C8L}
{O1P, N2P, N1P, C2P, C1P, C6P, C5P, C4P, C3P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1M, N1M, N2M, C1M, C2M, C3M, C4M, C5M, C6M, C7M, C8M}
{O1P, N1P, N2P, C1P, C2P, C3P, C4P, C5P, C6P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1N, N1N, N2N, C1N, C2N, C3N, C4N, C5N, C6N, C7N, C8N}
{O1P, N2P, N1P, C2P, C1P, C6P, C5P, C4P, C3P, C7P, C8P} sigma for 1-2: 0.01,
1-3: 0.02
as
{O1O, N1O, N2O, C1O, C2O, C3O, C4O, C5O, C6O, C7O, C8O}
{P1T, C5T, C6T, C7T, C8T} sigma for 1-2: 0.01, 1-3: 0.02
{P1T, C9T, C10T, C11T, C12T} sigma for 1-2: 0.01, 1-3: 0.02
{P1T, C13T, C14T, C15T, C16T} sigma for 1-2: 0.01, 1-3: 0.02
as
{P1T, C1T, C2T, C3T, C4T}
{P1X, C5X, C6X, C7X, C8X} sigma for 1-2: 0.01, 1-3: 0.02
{P1X, C9X, C10X, C11X, C12X} sigma for 1-2: 0.01, 1-3: 0.02
{P1X, C13X, C14X, C15X, C16X} sigma for 1-2: 0.01, 1-3: 0.02
as
{P1X, C1X, C2X, C3X, C4X}
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B), C1C(H1C), C2C(H2C), C2D(H2D),
 C1D(H1D), C1E(H1E), C2E(H2E), C1F(H1F), C2F(H2F), C1G(H1G), C2G(H2G), C1H(H1H),
  C2H(H2H), C1I(H1I), C2I(H2I), C1J(H1J), C2J(H2J), C1K(H1K), C2K(H2K),
 C1L(H1L), C2L(H2L), C1M(H1M), C2M(H2M), C1N(H1N), C2N(H2N), C1O(H1O), C2O(H2O),
  C2P(H2P), C1P(H1P)
6.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), C6D(H6DA,H6DB), C5D(H5DA,H5DB), C4D(H4DA,H4DB), C3D(H3DA,
 H3DB), C8D(H8DA,H8DB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB),
 C6E(H6EA,H6EB), C8E(H8EA,H8EB), C3F(H3FA,H3FB), C4F(H4FA,H4FB), C5F(H5FA,H5FB),
  C6F(H6FA,H6FB), 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), C3I(H3IA,H3IB), C4I(H4IA,H4IB),
  C5I(H5IA,H5IB), C6I(H6IA,H6IB), C8I(H8IA,H8IB), C3J(H3JA,H3JB), C4J(H4JA,
 H4JB), C5J(H5JA,H5JB), C6J(H6JA,H6JB), C8J(H8JA,H8JB), C3K(H3KA,H3KB),
 C4K(H4KA,H4KB), C5K(H5KA,H5KB), C6K(H6KA,H6KB), C8K(H8KA,H8KB), C3L(H3LA,H3LB),
  C4L(H4LA,H4LB), C5L(H5LA,H5LB), C6L(H6LA,H6LB), C8L(H8LA,H8LB), C3M(H3MA,
 H3MB), C4M(H4MA,H4MB), C5M(H5MA,H5MB), C6M(H6MA,H6MB), C8M(H8MA,H8MB),
 C3N(H3NA,H3NB), C4N(H4NA,H4NB), C5N(H5NA,H5NB), C6N(H6NA,H6NB), C8N(H8NA,H8NB),
  C3O(H3OA,H3OB), C4O(H4OA,H4OB), C5O(H5OA,H5OB), C6O(H6OA,H6OB), C8O(H8OA,
 H8OB), C6P(H6PA,H6PB), C5P(H5PA,H5PB), C4P(H4PA,H4PB), C3P(H3PA,H3PB),
 C8P(H8PA,H8PB), C1T(H1TA,H1TB), C2T(H2TA,H2TB), C3T(H3TA,H3TB), C5T(H5TA,H5TB),
  C6T(H6TA,H6TB), C7T(H7TA,H7TB), C9T(H9TA,H9TB), C10T(H10C,H10D), C11T(H11C,
 H11D), C13T(H13C,H13D), C14T(H14C,H14D), C15T(H15C,H15D), C1X(H1XA,H1XB),
 C2X(H2XA,H2XB), C3X(H3XA,H3XB), C5X(H5XA,H5XB), C6X(H6XA,H6XB), C7X(H7XA,H7XB),
  C9X(H9XA,H9XB), C10X(H10A,H10B), C11X(H11A,H11B), C13X(H13A,H13B), C14X(H14A,
 H14B), C15X(H15A,H15B)
6.c Idealised Me refined as rotating group:
 C4T(H4TA,H4TB,H4TC), C8T(H8TA,H8TB,H8TC), C12T(H12D,H12E,H12F), C16T(H16D,
 H16E,H16F), C4X(H4XA,H4XB,H4XC), C8X(H8XA,H8XB,H8XC), C12X(H12A,H12B,H12C),
 C16X(H16A,H16B,H16C), C2S(H2SA,H2SB,H2SC), C1S(H1SA,H1SB,H1SC), C3S(H3SA,H3SB,
 H3SC), C4S(H4SA,H4SB,H4SC)
6.d Idealised tetrahedral OH refined as rotating group:
 O2S(H2S), O1S(H1S), O3S(H3S), O4S(H4S)
;
_shelx_res_checksum              86080
_shelx_hkl_checksum              18980
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'