Supramolecular interactions between ethylene-bridged oligoureas: nanorings and chains formed by cooperative positive allostery
Tilly, David P.; Žabka, Matej; Vitorica-Yrzebal, Inigo; Sparkes, Hazel Anne; Pridmore, Natalie E.; Clayden, Jonathan; Chemical Science  (2022) –; doi:10.1039/D2SC04716K

data_1567852
_publ_section_title
;
 Supramolecular interactions between ethylene-bridged oligoureas:
 nanorings and chains formed by cooperative positive allostery
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04716K
_journal_year                    2022
_chemical_formula_moiety         'C29 H30 F6 N6 O3'
_chemical_formula_sum            'C29 H30 F6 N6 O3'
_chemical_formula_weight         624.59
_chemical_melting_point          458
_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     iterative
_audit_creation_date             2019-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0383(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2730(3)
_cell_length_b                   19.1589(4)
_cell_length_c                   15.2648(4)
_cell_measurement_reflns_used    8842
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.28
_cell_volume                     2948.83(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39105
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.725
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0716 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8428. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     356
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0454P)^2^+1.6032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5101
_reflns_number_total             6760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           dte126
_cod_original_cell_volume        2948.82(13)
_cod_database_code               1567852
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.952
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C19 \\sim C20A-C19A
 with sigma of 0.01
 C11-C10 \\sim C11A-C10A
 with sigma of 0.01
 C19-C11 \\sim C19A-C11A
 with sigma of 0.01
 C7-F1 \\sim C7-F1A \\sim C7-F2 \\sim C7-F2A \\sim C7-F3 \\sim C7-F3A
 with sigma of 0.01
 F1-F2 \\sim F1A-F2A \\sim F2-F3 \\sim F2A-F3A \\sim F3-F1 \\sim F3A-F1A
 with sigma of 0.01
 N3-C11 \\sim N3A-C11A
 with sigma of 0.01
 C20-N3 \\sim C20A-N3A
 with sigma of 0.01
 N3-C10 \\sim N3A-C10A
 with sigma of 0.01
 C27-N5 \\sim C27-N5A
 with sigma of 0.01
 C28-N5 \\sim C28A-N5A
 with sigma of 0.01
 C28-C29 \\sim C28A-C29A
 with sigma of 0.01
 N5-C29 \\sim N5A-C29A
 with sigma of 0.01
 N5-C20 \\sim N5A-C20A
 with sigma of 0.01
 N5-C19 \\sim N5A-C19A
 with sigma of 0.01
 C10-N2 \\sim C10A-N2A
 with sigma of 0.01
 C9-N2 \\sim C9-N2A
 with sigma of 0.01
 C11-N2 \\sim C11A-N2A
 with sigma of 0.01
 C12-N3 \\sim C12A-N3A
 with sigma of 0.01
 C12-O2 \\sim C12A-O2A
 with sigma of 0.01
 C12-N4 \\sim C12A-N4A
 with sigma of 0.01
 N4-O2 \\sim N4A-O2A
 with sigma of 0.01
 N4-C13 \\sim N4A-C13
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C10A \\sim C11 \\sim C11A \\sim C12 \\sim C12A \\sim C19 \\sim C19A
\\sim C20 \\sim C20A \\sim C28 \\sim C28A \\sim C29 \\sim C29A \\sim N2 \\sim
N2A \\sim N3 \\sim N3A \\sim N4 \\sim N4A \\sim N5 \\sim N5A \\sim O2 \\sim
O2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C28A)=
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(N2A)=Sof(H2AA)=
 Sof(N3A)=Sof(N4A)=Sof(H4AA)=Sof(N5A)=Sof(O2A)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(N2)=Sof(H2A)=Sof(N3)=Sof(N4)=
 Sof(H4A)=Sof(N5)=Sof(O2)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D), C11(H11A,H11B), C11A(H11C,H11D), C19(H19A,
 H19B), C19A(H19C,H19D), C20(H20A,H20B), C20A(H20C,H20D), C28(H28A,H28B),
 C28A(H28C,H28D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N2A(H2AA), N4A(H4AA)
5.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;
_shelx_res_checksum              83110
_shelx_hkl_checksum              92843
_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'