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_1567843
_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         'C22 H24 F6 N4 O2'
_chemical_formula_sum            'C22 H24 F6 N4 O2'
_chemical_formula_weight         490.45
_chemical_melting_point          436
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-15
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            36
_cell_length_a                   31.7595(6)
_cell_length_b                   31.7595(6)
_cell_length_c                   24.6991(6)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.22
_cell_volume                     21575.4(8)
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58951
_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         26.372
_diffrn_reflns_theta_min         1.108
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0682 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.8699. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             9144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.455
_exptl_crystal_size_min          0.241
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     852
_refine_ls_number_reflns         9812
_refine_ls_number_restraints     598
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0626P)^2^+38.8182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1346
_refine_special_details
;
One of the molecules and some of the CF3 groups were disordered, 
the occupancies were refined with their sum set to equal 1.  
Restraints were applied to the part with smaller occupancy ~0.2 
and the CF3 groups to maintain sensible geometric parameters. 
Restraints or constraints were applied to thermal parameters to
maintain sensible values.  Refined as a twin 0 1 0 1 0 0 0 0 -1,
BASF 0.3245(10).
;
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7995
_reflns_number_total             9812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testr1
_cod_original_cell_volume        21575.4(10)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1567843
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6754(10)
 0.3246(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C32A-C26A = C23A-C22A = C22A-C21A = C33A-C25A
 1.54 with sigma of 0.01
 N7A-C33A = N6A-C25A = N6A-C32A
 1.47 with sigma of 0.01
 F1-F2 = F2-F3 = F3-F1 = F1A-F2A = F1A-F3A = F2A-F3A
 2.14 with sigma of 0.01
 F2A-C19 \\sim F2-C19 \\sim F3-C19 \\sim F3A-C19 \\sim F1-C19 \\sim F1A-C19
\\sim F4A-C20 \\sim F5-C20 ~
 F5A-C20 \\sim F6-C20 \\sim F6A-C20 \\sim F4-C20 \\sim F9-C41 \\sim F7A-C41
\\sim F7-C41 \\sim F8A-C41 \\sim F8-
 C41 \\sim F9A-C41
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F4A \\sim F5 \\sim F5A \\sim F6 \\sim F6A \\sim F4: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F8 \\sim F9A \\sim F9 \\sim F7A \\sim F7 \\sim F8A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F1A \\sim F1 \\sim F3A \\sim F3 \\sim F2A \\sim F2: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
N5A \\sim C22A \\sim C21A \\sim C23A \\sim O4A \\sim N7A \\sim C24A \\sim O3A
\\sim N6A \\sim C25A \\sim C32A \\sim C33A \\sim C26A \\sim C29A \\sim C28A
\\sim C27A \\sim C31A \\sim C30A \\sim O3 \\sim O4 \\sim N5 \\sim N6 \\sim N7
\\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28
\\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C34A \\sim
N8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C26A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C30A) \\sim Ueq,
Uanis(C29A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C27A) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2A) = Uanis(F2)
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(H8B)=Sof(N5A)=Sof(H5A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C34A)=Sof(O4A)=Sof(N7A)=
 Sof(H7A)=Sof(C24A)=Sof(O3A)=Sof(N6A)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C32A)=
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C26A)=Sof(C31A)=
 Sof(H31A)=Sof(C30A)=Sof(H30A)=Sof(C29A)=Sof(H29A)=Sof(C28A)=Sof(H28A)=
 Sof(C27A)=Sof(H27A)=1-FVAR(2)
 Sof(O3)=Sof(O4)=Sof(N5)=Sof(H5)=Sof(N6)=Sof(N7)=Sof(H7)=Sof(H8A)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(H23C)=Sof(C24)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(C27)=Sof(H27)=
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=FVAR(2)
 Sof(F7A)=Sof(F9A)=Sof(F8A)=1-FVAR(3)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(4)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C22(H22), C22A(H22A)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5B,H5C), C11(H11A,H11B), C12(H12A,H12B), C25(H25A,H25B), C32(H32A,H32B),
 C33(H33A,H33B), C25A(H25C,H25D), C32A(H32C,H32D), C33A(H33C,H33D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N4(H4), C0AA(H0AA), C1AA(H1AA), C7(H7B), C8(H8), C9(H9),
 C10(H10), C15(H15), C17(H17), N5(H5), N7(H7), N8(H8A), N8(H8B), C27(H27),
 C28(H28), C29(H29), C30(H30), C31(H31), C36(H36), C38(H38), C40(H40), N5A(H5A),
  N7A(H7A), C31A(H31A), C30A(H30A), C29A(H29A), C28A(H28A), C27A(H27A)
6.d Fitted hexagon refined as free rotating group:
 C26A(C31A,C30A,C29A,C28A,C27A)
6.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C),
 C21A(H21D,H21E,H21F), C23A(H23D,H23E,H23F)
;
_shelx_res_checksum              47571
_shelx_hkl_checksum              20445
_olex2_submission_special_instructions 'No special instructions were received'