Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril
E. Prigorchenko; M. Oeren; S. Kaabel; M. Fomitsenko; I. Reile; I. Jarving; T. Tamm; F. Topic; K. Rissanen; R. Aav; Chem.Commun. 51 (2015) 10921–; doi:10.1039/C5cc04101E

data_7117387
_publ_section_title
;
 Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril
;
_journal_name_full               Chem.Commun.
_journal_page_first              10921
_journal_paper_doi               10.1039/C5cc04101E
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C64 H96 N16 O8), 6.75(C H4 O), H2 O'
_chemical_formula_sum            'C134.75 H221 N32 O23.75'
_chemical_formula_weight         2669.42
_chemical_name_common            (all-R)cyclohexylhemicucurbit[8]uril
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-03-10 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.33(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.510(4)
_cell_length_b                   27.312(3)
_cell_length_c                   17.957(3)
_cell_measurement.radiation      'Cu K\a'
_cell_measurement_temperature    200.0(1)
_cell_measurement_theta_max      67.567
_cell_measurement_theta_min      22.516
_cell_volume                     8048(3)
_computing_cell_refinement
;
XDS (Kabsch, W. 2010)
;
_computing_data_collection
;
HKL-2000
Rigaku Collection Strategy
;
_computing_data_reduction
;
XDS (Kabsch, W. 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean 22.17
_diffrn_detector_type            'CCD MSC saturn944'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroGrippersTM'
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            84720
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.550
_diffrn_reflns_theta_max         67.553
_diffrn_reflns_theta_min         2.476
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-003'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_description       block
_exptl_crystal_F_000             2887
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
TITL cycHC_SMosher_x3 in P21 #4
CELL   16.5100   27.3120   17.9570     90.00     96.33     90.00
SPGR P21
C101 0.267 0.308 0.655 !       3.40 eA-3
C102 0.913 0.690 0.950 !       2.16 eA-3
C103 0.253 0.342 0.642 !       2.15 eA-3
C104 0.728 0.729 0.433 !       1.92 eA-3
C105 0.806 0.725 0.503 !       1.79 eA-3
C106 0.439 0.986 0.465 !       1.47 eA-3
C107 0.381 0.985 0.469 !       1.40 eA-3
C108 0.878 0.655 0.048 !       1.20 eA-3
C109 0.870 0.713 0.511 !       0.92 eA-3
Q110 0.470 0.096 0.940 !       0.74 eA-3
Q111 0.030 0.037 0.560 !       0.67 eA-3
C112 0.392 0.375 0.579 !       0.60 eA-3
Q113 0.029 0.015 0.579 !       0.60 eA-3
C114 0.177 0.161 0.474 !       0.59 eA-3
Q115 0.519 0.967 0.967 !       0.53 eA-3
C116 0.119 0.382 0.688 !       0.52 eA-3
Q117 0.572 0.465 0.029 !       0.52 eA-3
C118 0.120 0.151 0.439 !       0.51 eA-3
;
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 10228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1775
_refine_ls_number_reflns         27756
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+1.6358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1666
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                23872
_reflns_number_total             27756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04101e2.cif
_cod_data_source_block           (all-R)-cycHC[8]
_cod_database_code               7117387
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.812
_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, All O(H,H) groups
2. Restrained distances
 H1M-O206_$1
 1.914 with sigma of 0.02
 H8M-O106 = H6M-O4M
 2 with sigma of 0.02
 H1SA-O103_$2
 1.929 with sigma of 0.02
 H1SB-O8M
 1.787 with sigma of 0.02
 O202-H7M
 1.923 with sigma of 0.02
 O2M-C2M \\sim O8M-C8M \\sim O1M-C1M \\sim O9M-C9M \\sim O7M-C7M \\sim O6M-C6M
\\sim O4M-C4M \\sim O3M-C3M
 \\sim O5M-C5M
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O7M) \\sim Ueq, Uanis(C7M) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Others
 Fixed Sof: O3M(0.75) H3M(0.75) O8M(0.75) H8M(0.75) O4M(0.75) H4M(0.75)
 C4M(0.75) H4MA(0.75) H4MB(0.75) H4MC(0.75) C8M(0.75) H8MA(0.75) H8MB(0.75)
 H8MC(0.75) C7M(0.5) H7MA(0.5) H7MB(0.5) H7MC(0.5) O7M(0.5) H7M(0.5) C3M(0.75)
 H3MA(0.75) H3MB(0.75) H3MC(0.75) O5M(0.5) H5M(0.5) C5M(0.5) H5MA(0.5)
 H5MB(0.5) H5MC(0.5) O6M(0.5) H6M(0.5) C6M(0.5) H6MA(0.5) H6MB(0.5) H6MC(0.5)
5.a Free rotating group:
 O1S(H1SA,H1SB)
5.b Ternary CH refined with riding coordinates:
 C257(H257), C202(H202), C242(H242), C249(H249), C201(H201), C134(H134),
 C141(H141), C109(H109), C102(H102), C258(H258), C133(H133), C226(H226),
 C250(H250), C149(H149), C150(H150), C142(H142), C101(H101), C218(H218),
 C241(H241), C209(H209), C210(H210), C217(H217), C125(H125), C118(H118),
 C157(H157), C117(H117), C158(H158), C225(H225), C126(H126), C110(H110),
 C234(H234), C233(H233)
5.c Secondary CH2 refined with riding coordinates:
 C163(H16A,H16B), C247(H24A,H24B), C239(H23A,H23B), C139(H13A,H13B), C231(H23C,
 H23D), C255(H25A,H25B), C215(H21A,H21B), C131(H13C,H13D), C219(H21C,H21D),
 C223(H22A,H22B), C207(H20A,H20B), C251(H25C,H25D), C115(H11A,H11B), C155(H15A,
 H15B), C107(H10A,H10B), C147(H14A,H14B), C263(H26A,H26B), C206(H20C,H20D),
 C220(H22C,H22D), C203(H20E,H20F), C151(H15C,H15D), C254(H25E,H25F), C123(H12A,
 H12B), C259(H25G,H25H), C222(H22E,H22F), C154(H15E,H15F), C243(H24C,H24D),
 C246(H24E,H24F), C152(H15G,H15H), C252(H25I,H25J), C112(H11C,H11D), C227(H22G,
 H22H), C211(H21E,H21F), C162(H16C,H16D), C161(H16E,H16F), C127(H12C,H12D),
 C130(H13E,H13F), C261(H26C,H26D), C111(H11E,H11F), C235(H23E,H23F), C135(H13G,
 H13H), C138(H13I,H13J), C120(H12E,H12F), C205(H20G,H20H), C153(H15I,H15J),
 C143(H14C,H14D), C230(H23G,H23H), C253(H25K,H25L), C221(H22I,H22J), C113(H11G,
 H11H), C159(H15K,H15L), C129(H12G,H12H), C204(H20I,H20J), C114(H11I,H11J),
 C146(H14E,H14F), C103(H10C,H10D), C122(H12I,H12J), C105(H10E,H10F), C136(H13K,
 H13L), C260(H26E,H26F), C160(H16G,H16H), C244(H24G,H24H), C236(H23I,H23J),
 C262(H26G,H26H), C245(H24I,H24J), C145(H14G,H14H), C238(H23K,H23L), C212(H21G,
 H21H), C137(H13M,H13N), C144(H14I,H14J), C106(H10G,H10H), C128(H12K,H12L),
 C104(H10I,H10J), C119(H11K,H11L), C214(H21I,H21J), C229(H22K,H22L), C237(H23M,
 H23N), C121(H12M,H12N), C228(H22M,H22N), C213(H21K,H21L)
5.d Me refined with riding coordinates:
 C6M(H6MA,H6MB,H6MC)
5.e Tetrahedral OH refined with riding coordinates:
 O7M(H7M)
5.f Idealised Me refined as rotating group:
 C9M(H9MA,H9MB,H9MC), C4M(H4MA,H4MB,H4MC), C2M(H2MA,H2MB,H2MC), C8M(H8MA,H8MB,
 H8MC), C7M(H7MA,H7MB,H7MC), C3M(H3MA,H3MB,H3MC), C1M(H1MA,H1MB,H1MC), C5M(H5MA,
 H5MB,H5MC)
5.g Idealised tetrahedral OH refined as rotating group:
 O2M(H2M), O9M(H9M), O3M(H3M), O8M(H8M), O4M(H4M), O1M(H1M), O5M(H5M), O6M(H6M)
;
_shelx_res_checksum              55218
_shelx_hkl_checksum              82932
_shelx_fab_checksum              90107
_olex2_submission_special_instructions 'No special instructions were received'