Tiara[ n]uril: A Glycoluril-Based Macrocyclic Host with Cationic Walls.
Chandrakumar, Pradeep Kumar; Dhiman, Rajni; Woodward, Clifford E.; Iranmanesh, Hasti; Beves, Jonathon E.; Day, Anthony I.; The Journal of organic chemistry 84 (2019) 3826–3831; doi:10.1021/acs.joc.8b02913

data_4034274
_publ_section_title
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 Tiara[ n]uril: A Glycoluril-Based Macrocyclic Host with Cationic Walls.
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_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3826
_journal_page_last               3831
_journal_paper_doi               10.1021/acs.joc.8b02913
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety
'16(F6 P), 34(H2 O), 6(C H4 O), 8(C37 H48 N16 O6), 15(O)'
_chemical_formula_sum            'C302 H476 F96 N128 O103 P16'
_chemical_formula_weight         9867.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-20
_audit_creation_method
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Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.435(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   19.6438(14)
_cell_length_b                   20.3232(15)
_cell_length_c                   26.513(2)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      2.32
_cell_volume                     10295.0(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       '<i>APEX3 </i>(Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            210303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.062
_diffrn_reflns_theta_min         1.276
_diffrn_source                   'Incoatec I\mS microfocus X-ray source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1378 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.7598.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       plate
_exptl_crystal_F_000             5112
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.997
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1524
_refine_ls_number_reflns         22592
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0784
_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^)+(0.0879P)^2^+39.5016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14893
_reflns_number_total             22592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02913_si_002.cif
_cod_data_source_block           hasti06012017_0m_a
_cod_original_cell_volume        10294.9(13)
_cod_database_code               4034274
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  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
 C1AA-O0BA = O1BA-C0AA
 1.45 with sigma of 0.02
 O0BA-C1AA
 1.45 with sigma of 0.02
 O1BA-C0AA
 1.45 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C0AA, O1BA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O0BA(0.75) H0BA(0.75) C1AA(0.75) H1AA(0.75) H1AB(0.75) H1AC(0.75)
 O1BA(0.75) H1BA(0.75) C0AA(0.75) H0AA(0.75) H0AB(0.75) H0AC(0.75) O2AA(0.75)
 H2AA(0.75) H2AB(0.75) O8AA(0.75) O5BA(0.75) H5BA(0.75) H5BB(0.75)
5.a Free rotating group:
 O0AA(H0AD,H0AE), O1AA(H1AD,H1AE), O2AA(H2AA,H2AB), O4AA(H4AA,H4AB), O4BA(H4BA,
 H4BB), O5AA(H5AA,H5AB), O9AA(H9AA,H9AB), O5BA(H5BA,H5BB)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C13(H13A,H13B), C20(H20A,H20B), C21(H21A,H21B),
 C28(H28A,H28B), C29(H29A,H29B), C36(H36A,H36B), C37(H37A,H37B), C43(H43A,H43B),
  C49(H49A,H49B), C50(H50A,H50B), C57(H57A,H57B), C58(H58A,H58B), C65(H65A,
 H65B), C66(H66A,H66B), C73(H73A,H73B), C74(H74A,H74B)
5.c Idealised Me refined as rotating group:
 C1AA(H1AA,H1AB,H1AC), C0AA(H0AA,H0AB,H0AC), C1(H1A,H1B,H1C), C5(H5A,H5B,H5C),
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C),
  C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C31(H31A,H31B,H31C), C35(H35A,H35B,
 H35C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C45(H45A,H45B,H45C), C48(H48A,
 H48B,H48C), C53(H53A,H53B,H53C), C56(H56A,H56B,H56C), C60(H60A,H60B,H60C),
 C64(H64A,H64B,H64C), C68(H68A,H68B,H68C), C72(H72A,H72B,H72C)
5.d Idealised tetrahedral OH refined as rotating group:
 O0BA(H0BA), O1BA(H1BA)
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_olex2_submission_special_instructions 'No special instructions were received'