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_1544706
_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, C F3 O3 S, 2(C H4 O)'
_chemical_formula_sum            'C83 H140 F3 N17 O13 S'
_chemical_formula_weight         1673.17
_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             2016-08-20
_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                   20.27229(12)
_cell_length_b                   20.73280(13)
_cell_length_c                   21.02695(11)
_cell_measurement_reflns_used    40740
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.8720
_cell_measurement_theta_min      3.6760
_cell_volume                     8837.66(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 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -116.00  -18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000  150.0000 98

  2 omega  -49.00   33.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -30.0000 82

  3 omega  -96.00   -2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000    0.0000 94

  4 omega -116.00  -18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000 -120.0000 98

  5 omega   34.00  136.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -61.0000 -150.0000 102

  6 omega   78.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  120.0000 100

  7 omega   34.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -45.0000   60.0000 65

  8 omega   78.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   60.0000 -127.8749 100

  9 omega   24.00  108.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   90.0000 84

 10 omega   33.00  122.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000   60.0000 89

 11 omega   75.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   73.0000   82.1508 103

 12 omega   77.00  178.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000 -174.3620 101

 13 omega -115.00  -14.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000    0.0000 101
;
_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      0.0730753000
_diffrn_orient_matrix_UB_12      0.0201633000
_diffrn_orient_matrix_UB_13      -0.0029453000
_diffrn_orient_matrix_UB_21      -0.0178449000
_diffrn_orient_matrix_UB_22      0.0662430000
_diffrn_orient_matrix_UB_23      0.0283894000
_diffrn_orient_matrix_UB_31      0.0106576000
_diffrn_orient_matrix_UB_32      -0.0270726000
_diffrn_orient_matrix_UB_33      0.0674533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            65288
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.750
_diffrn_reflns_theta_max         74.301
_diffrn_reflns_theta_min         3.028
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.678
_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    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             3616
_exptl_crystal_size_max          0.6163
_exptl_crystal_size_mid          0.2939
_exptl_crystal_size_min          0.2541
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 7489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1176
_refine_ls_number_reflns         17735
_refine_ls_number_restraints     2566
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0977P)^2^+2.7336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                17237
_reflns_number_total             17735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05058a2.cif
_cod_data_source_block           all-R_cycHC8_TBACF3SO3
_cod_depositor_comments
'Adding full bibliography for 1544701--1544706.cif.'
_cod_original_cell_volume        8837.65(9)
_cod_database_code               1544706
_chemical_oxdiff_formula         'C83 H140 O13 N17 S F3'
_reflns_odcompleteness_completeness 99.97
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1S-O1S \\sim C2S-O2S \\sim C2SB-O2SB
 with sigma of 0.01
 C1N-F3N \\sim C1N-F2N \\sim C1N-F1N \\sim C1M-F3M \\sim C1M-F1M \\sim C1M-F2M
 with sigma of 0.02
 F3N-F2N \\sim F3N-F1N \\sim F2N-F1N \\sim F3M-F1M \\sim F3M-F2M \\sim F1M-F2M
 with sigma of 0.02
 O2N-O1N \\sim O2N-O3N \\sim O1N-O3N \\sim O2M-O1M \\sim O2M-O3M \\sim O1M-O3M
 with sigma of 0.02
 S1N-O2N \\sim S1N-O1N \\sim S1N-O3N \\sim S1M-O2M \\sim S1M-O1M \\sim S1M-O3M
 with sigma of 0.02
 C1N-O2N \\sim C1N-O1N \\sim C1N-O3N \\sim C1M-O2M \\sim C1M-O1M \\sim C1M-O3M
 with sigma of 0.01
 S1N-F3N \\sim S1N-F2N \\sim S1N-F1N \\sim S1M-F3M \\sim S1M-F1M \\sim S1M-F2M
 with sigma of 0.01
 C1N-S1N \\sim C1M-S1M
 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
 O2SB, C2SB
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
S1M \\sim F1M \\sim F2M \\sim F3M \\sim O1M \\sim O2M \\sim O3M \\sim C1M \\sim
S1N \\sim F1N \\sim F2N \\sim F3N \\sim O1N \\sim O2N \\sim O3N \\sim C1N:
within 2.8A with sigma of 0.02 and sigma for terminal atoms of 0.02
O2SB \\sim C2SB \\sim O2S \\sim C2S: within 2.8A with sigma of 0.01 and sigma
for terminal atoms of 0.01
Uanis(C2SB) \\sim Ueq, Uanis(O2SB) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.05
5. Rigid body (RIGU) restrains
 C2A, C1A, C6A, C5A, C4A, C3A, C7A, C8A, C0AA, C1E, C2E, C3E, C4E, C5E, C6E,
 C7E, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C1C, C2C, C3C, C4C, C5C, C6C, C7C,
  C8C, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D, 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, C1TB, C2TB, C1M, C1N, C1S, C2SB, C2S, N2A, N1A, N1E, N2E,
 N1B, N2B, N1C, N2C, N1D, N2D, N1F, N2F, N1G, N2G, N1H, N2H, N1T, O1A, O1E, O1B,
  O1C, O1D, O1F, O1G, O1H, O1M, O2M, O3M, O1N, O2N, O3N, O1S, O2SB, O2S, S1M,
 S1N, F1M, F2M, F3M, F1N, F2N, F3N
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C8A, O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A} sigma for 1-2: 0.02,
1-3: 0.02
as
{C0AA, O1E, N1E, N2E, C1E, C2E, C3E, C4E, C5E, C6E, C7E}
{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, 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}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.04
as
{C5T, C6T, C7T, C8T}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.04
as
{C9T, C10T, C11T, C12T}
{C1T, C2T, C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.04
as
{C13T, C14T, C15T, C16T}
{C3T, C4T} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1TB, C2TB}
7. Others
 Sof(H10C)=Sof(H10D)=Sof(C1TB)=Sof(H1TC)=Sof(H1TD)=Sof(C2TB)=Sof(H2TC)=
 Sof(H2TD)=Sof(H2TE)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11T)=Sof(H11A)=Sof(H11B)=Sof(C12T)=Sof(H12A)=
 Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(S1M)=Sof(F1M)=Sof(F2M)=Sof(F3M)=Sof(O1M)=Sof(O2M)=Sof(O3M)=Sof(C1M)=1-
 FVAR(2)
 Sof(S1N)=Sof(F1N)=Sof(F2N)=Sof(F3N)=Sof(O1N)=Sof(O2N)=Sof(O3N)=Sof(C1N)=FVAR(2)
 Sof(O2SB)=Sof(H2SG)=Sof(C2SB)=Sof(H2SD)=Sof(H2SE)=Sof(H2SF)=1-FVAR(3)
 Sof(O2S)=Sof(H2S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(3)
8.a Ternary CH refined with riding coordinates:
 C2A(H2A), C1A(H1A), C1E(H1E), C2E(H2E), C1B(H1B), C2B(H2B), C1C(H1C),
 C2C(H2C), C1D(H1D), C2D(H2D), C1F(H1F), C2F(H2F), C1G(H1G), C2G(H2G), C1H(H1H),
  C2H(H2H)
8.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C5A(H5AA,H5AB), C4A(H4AA,H4AB), C3A(H3AA,H3AB), C8A(H8AA,
 H8AB), C0AA(H0AA,H0AB), C3E(H3EA,H3EB), C4E(H4EA,H4EB), C5E(H5EA,H5EB),
 C6E(H6EA,H6EB), 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), 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), C10T(H10C,H10D), C11T(H11A,H11B), C13T(H13A,H13B),
 C14T(H14A,H14B), C15T(H15A,H15B), C1TB(H1TC,H1TD)
8.c Idealised Me refined as rotating group:
 C4T(H4TA,H4TB,H4TC), C8T(H8TA,H8TB,H8TC), C12T(H12A,H12B,H12C), C16T(H16A,
 H16B,H16C), C2TB(H2TC,H2TD,H2TE), C1S(H1SA,H1SB,H1SC), C2SB(H2SD,H2SE,H2SF),
 C2S(H2SA,H2SB,H2SC)
8.d Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O2SB(H2SG), O2S(H2S)
;
_shelx_res_checksum              13169
_shelx_hkl_checksum              12898
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'