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_1567842
_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         'C31 H42 F6 N6 O3'
_chemical_formula_sum            'C31 H42 F6 N6 O3'
_chemical_formula_weight         660.70
_chemical_melting_point          441
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-31
_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                101.789(2)
_cell_angle_beta                 111.249(2)
_cell_angle_gamma                97.465(2)
_cell_formula_units_Z            4
_cell_length_a                   14.5044(5)
_cell_length_b                   14.9547(5)
_cell_length_c                   17.2099(6)
_cell_measurement_reflns_used    7484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.33
_cell_volume                     3319.6(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_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 CCD'
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48350
_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         25.350
_diffrn_reflns_theta_min         1.427
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0648 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.8302. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     949
_refine_ls_number_reflns         12166
_refine_ls_number_restraints     328
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+1.7692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7559
_reflns_number_total             12166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testt1
_cod_database_code               1567842
_shelx_shelxl_version_number     2017/1
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C4 \\sim N2A-C4 \\sim N2A-C5 \\sim N2-C5
 with sigma of 0.01
 N2A-C12A \\sim N2-C12 \\sim N3-C13 \\sim N3A-C13A \\sim N3-C21 \\sim N3A-C21A
\\sim N5-C22 \\sim N5-C22A
 with sigma of 0.01
 C13A-C12A \\sim C13-C12 \\sim C22-C21 \\sim C22A-C21A
 with sigma of 0.01
 N3-C14 \\sim N3A-C14
 with sigma of 0.01
 N8A-C36 \\sim N8-C36 \\sim N8A-C35 \\sim N8-C35 \\sim N9-C45 \\sim N9A-C45
\\sim N9-C52 \\sim N9A-C52
 with sigma of 0.01
 N8A-C43A \\sim N8-C43 \\sim N9-C44 \\sim N9A-C44A
 with sigma of 0.01
 C44-C43 \\sim C44A-C43A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim N2A \\sim C12 \\sim C12A \\sim C13 \\sim C13A \\sim N3 \\sim C21 \\sim
N3A \\sim C22 \\sim C21A \\sim C22A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
N8 \\sim N9 \\sim C43 \\sim C44 \\sim C43A \\sim C44A \\sim N8A \\sim N9A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N8A) = Uanis(N8)
4. Others
 Sof(H5B)=Sof(H5BC)=Sof(H5BD)=Sof(N2A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=
 Sof(H13C)=Sof(H13D)=Sof(N3A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=1-FVAR(1)
 Sof(N2)=Sof(N3)=Sof(H5A)=Sof(H5AA)=Sof(H5AB)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=FVAR(1)
 Sof(H36C)=Sof(H36D)=Sof(H52C)=Sof(H52D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=
 Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(N8A)=Sof(N9A)=1-FVAR(2)
 Sof(N8)=Sof(N9)=Sof(H36A)=Sof(H36B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=
 Sof(H44A)=Sof(H44B)=Sof(H52A)=Sof(H52B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C32(H32)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B),
  C22(H22A,H22B), C36(H36A,H36B), C36(H36C,H36D), C43(H43A,H43B), C44(H44A,
 H44B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B),
 C50(H50A,H50B), C52(H52A,H52B), C52(H52C,H52D), C53(H53A,H53B), C12A(H12C,
 H12D), C13A(H13C,H13D), C21A(H21C,H21D), C22A(H22C,H22D), C43A(H43C,H43D),
 C44A(H44C,H44D)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5A), N5(H5B), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C25(H25),
 C27(H27), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C56(H56),
  C58(H58), C60(H60)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C20(H20A,H20B,H20C), C33(H33A,H33B,H33C),
 C34(H34A,H34B,H34C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              1079
_shelx_hkl_checksum              85210
_olex2_submission_special_instructions 'No special instructions were received'