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_1544703
_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, 2(C H4 O), 1(B F4)'
_chemical_formula_sum            'C82 H140 B F4 N17 O10'
_chemical_formula_weight         1610.91
_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
_audit_creation_date             2016-08-19
_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                   20.03081(12)
_cell_length_b                   20.92663(13)
_cell_length_c                   20.97159(13)
_cell_measurement_reflns_used    47346
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.0100
_cell_measurement_theta_min      3.6710
_cell_volume                     8790.82(9)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(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 0.994
_diffrn_measurement_details
;
  1 omega  -45.00   29.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000   90.0000 74

  2 omega  -48.00   31.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -90.0000 79

  3 omega  -39.00   -4.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   19.0000  -30.0000 35

  4 omega -126.00  -76.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  171.0000  -75.9758 50

  5 omega  -84.00  -45.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000  -90.0000 39

  6 omega  -77.00   36.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   19.0000   30.0000 113

  7 omega    7.00   70.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000 -180.0000 63

  8 omega   64.00  120.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000   30.0000 56

  9 omega   95.00  122.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  150.0000 27

 10 omega   50.00  108.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -150.0000 58

 11 omega   61.00  107.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -77.0000   30.0000 46

 12 omega   39.00   98.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -45.0000 -180.0000 59

 13 omega   95.00  161.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  125.0000  150.0000 66

 14 omega  130.00  156.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   45.0000  150.0000 26

 15 omega   30.00   78.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000    0.0000 48

 16 omega   33.00   75.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  150.0000 42

 17 omega   27.00   92.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  150.0000 65

 18 omega   79.00  176.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   30.0000 -120.0000 97

 19 omega   54.00   90.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000 -150.0000 36

 20 omega   31.00   87.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000  120.0000 56

 21 omega   50.00   90.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -60.0000 40

 22 omega   31.00   86.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -30.0000  -90.0000 55

 23 omega   97.00  178.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   30.0000  -60.0000 81
;
_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      0.0012134000
_diffrn_orient_matrix_UB_12      -0.0172777000
_diffrn_orient_matrix_UB_13      0.0713908000
_diffrn_orient_matrix_UB_21      -0.0460092000
_diffrn_orient_matrix_UB_22      0.0572080000
_diffrn_orient_matrix_UB_23      0.0144555000
_diffrn_orient_matrix_UB_31      -0.0616440000
_diffrn_orient_matrix_UB_32      -0.0429797000
_diffrn_orient_matrix_UB_33      -0.0094201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            70925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         74.270
_diffrn_reflns_theta_min         3.051
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.763
_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    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.5093
_exptl_crystal_size_mid          0.1537
_exptl_crystal_size_min          0.1251
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 7595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1196
_refine_ls_number_reflns         17694
_refine_ls_number_restraints     2641
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0544
_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^)+(0.1091P)^2^+2.1808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                17291
_reflns_number_total             17694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05058a2.cif
_cod_data_source_block           all-R_cycHC8_TBABF4
_cod_depositor_comments
'Adding full bibliography for 1544701--1544706.cif.'
_cod_original_cell_volume        8790.81(9)
_cod_database_code               1544703
_chemical_oxdiff_formula         'C80 H132 O8 N17 B F4'
_reflns_odcompleteness_completeness 99.96
_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
 B1A-F1A = B1A-F2A = B1A-F3A = B1A-F4A
 1.3644 with sigma of 0.01
 F1A-F2A = F1A-F3A = F1A-F4A = F2A-F3A = F2A-F4A = F3A-F4A
 2.228065 with sigma of 0.02
 B1B-F1B = B1B-F2B = B1B-F3B = B1B-F4B
 1.3644 with sigma of 0.01
 F1B-F2B = F1B-F3B = F1B-F4B = F2B-F3B = F2B-F4B = F3B-F4B
 2.228065 with sigma of 0.02
 B1C-F1C = B1C-F2C = B1C-F3C = B1C-F4C
 1.3644 with sigma of 0.01
 F1C-F2C = F1C-F3C = F1C-F4C = F2C-F3C = F2C-F4C = F3C-F4C
 2.228065 with sigma of 0.02
 B1D-F1D = B1D-F2D = B1D-F3D = B1D-F4D
 1.3644 with sigma of 0.01
 F1D-F2D = F1D-F3D = F1D-F4D = F2D-F3D = F2D-F4D = F3D-F4D
 2.228065 with sigma of 0.02
 O2SA-C2SA \\sim O2SB-C2SB \\sim O1S-C1S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1B \\sim F2B \\sim F3B \\sim F4B \\sim B1B \\sim F1D \\sim F2D \\sim F3D \\sim
F4D \\sim B1D \\sim F1C \\sim F2C \\sim F3C \\sim F4C \\sim B1C \\sim F1A \\sim
F2A \\sim F3A \\sim F4A \\sim B1A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.02
O2SB \\sim C2SB \\sim O2SA \\sim C2SA: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.01
O1S \\sim C1S: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2SA) \\sim Ueq, Uanis(C2SA) \\sim Ueq, Uanis(O2SB) \\sim Ueq,
Uanis(C2SB) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 C2A, C1A, C6A, C5A, C4A, C3A, 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, C1F, C2F, C3F, C4F, C5F, C6F,
 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, C1S, C2SB, C2SA, N2A, N1A, N1B, N2B, N1C, N2C, N1D, N2D,
 N1E, N2E, N1F, N2F, N1G, N2G, N1H, N2H, N1T, O1A, O1B, O1C, O1D, O1E, O1F, O1G,
  O1H, O1S, O2SB, O2SA, F1B, F2B, F3B, F4B, F1D, F2D, F3D, F4D, F1C, F2C, F3C,
 F4C, F1A, F2A, F3A, F4A, B1B, B1D, B1C, B1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1A, N2A, N1A, C2A, C1A, C6A, C5A, C4A, C3A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B}
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1C, N1C, N2C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C}
{O1A, N2A, N1A, C2A, C1A, C6A, C5A, C4A, C3A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1D, N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D}
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1E, N1E, N2E, C1E, C2E, C3E, C4E, C5E, C6E, C7E, C8E}
{O1A, N2A, N1A, C2A, C1A, C6A, C5A, C4A, C3A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1F, N1F, N2F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F}
{O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1G, N1G, N2G, C1G, C2G, C3G, C4G, C5G, C6G, C7G, C8G}
{O1A, N2A, N1A, C2A, C1A, C6A, C5A, C4A, C3A, C7A, C8A} sigma for 1-2: 0.02,
1-3: 0.02
as
{O1H, N1H, N2H, C1H, C2H, C3H, C4H, C5H, C6H, C7H, C8H}
{N1T, C5T, C6T, C7T, C8T} sigma for 1-2: 0.01, 1-3: 0.04
{N1T, C9T, C10T, C11T, C12T} sigma for 1-2: 0.01, 1-3: 0.04
{N1T, C13T, C14T, C15T, C16T} sigma for 1-2: 0.01, 1-3: 0.04
as
{N1T, C1T, C2T, C3T, C4T}
6. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)+Sof(F4A)+Sof(B1A)]+1*[Sof(F1B)+Sof(F2B)+
 Sof(F3B)+Sof(F4B)+Sof(B1B)]+1*[Sof(F1C)+Sof(F2C)+Sof(F3C)+Sof(F4C)+Sof(B1C)]+1*
 [Sof(F1D)+Sof(F2D)+Sof(F3D)+Sof(F4D)+Sof(B1D)]=1 with esd of 0.001
 1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=FVAR(1)
 1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1.633*FVAR(2)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(B1A)=FVAR(2)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(B1B)=FVAR(3)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(F4C)=Sof(B1C)=FVAR(4)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=Sof(F4D)=Sof(B1D)=FVAR(5)
 Sof(O2SA)=Sof(H2SE)=Sof(C2SA)=Sof(H2SF)=Sof(H2SG)=Sof(H2SH)=1-FVAR(6)
 Sof(O2SB)=Sof(H2SB)=Sof(C2SB)=Sof(H2SA)=Sof(H2SC)=Sof(H2SD)=FVAR(6)
7.a Ternary CH refined with riding coordinates:
 C2A(H2A), C1A(H1A), C1B(H1B), C2B(H2B), C1C(H1C), C2C(H2C), C1D(H1D),
 C2D(H2D), C1E(H1E), C2E(H2E), C1F(H1F), C2F(H2F), C1G(H1G), C2G(H2G), C1H(H1H),
  C2H(H2H)
7.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C5A(H5AA,H5AB), C4A(H4AA,H4AB), C3A(H3AA,H3AB), 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), 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), 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)
7.c Idealised Me refined as rotating group:
 C4T(H4TA,H4TB,H4TC), C8T(H8TA,H8TB,H8TC), C12T(H12A,H12B,H12C), C16T(H16A,
 H16B,H16C), C1S(H1SA,H1SB,H1SC), C2SB(H2SA,H2SC,H2SD), C2SA(H2SF,H2SG,H2SH)
7.d Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O2SB(H2SB), O2SA(H2SE)
;
_shelx_res_checksum              32575
_shelx_hkl_checksum              2066
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'