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_1567849
_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         'C23 H26 F6 N4 O2'
_chemical_formula_sum            'C23 H26 F6 N4 O2'
_chemical_formula_weight         504.48
_chemical_melting_point          422
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-09
_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                 105.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.0463(4)
_cell_length_b                   21.9267(6)
_cell_length_c                   18.6546(5)
_cell_measurement_reflns_used    8952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.32
_cell_volume                     7117.8(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_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 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC 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  0.0684
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.937
_diffrn_reflns_theta_min         1.464
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7409. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             3144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1015
_refine_ls_number_reflns         17042
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0495P)^2^+4.5874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10765
_reflns_number_total             17042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testm1_CCDC1
_cod_database_code               1567849
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N10-C53 \\sim N10A-C53
 with sigma of 0.01
 N10A-C54A \\sim N10-C54
 with sigma of 0.01
 C55A-C54A \\sim C55-C54
 with sigma of 0.01
 N11-C55A \\sim N11-C55
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N10 \\sim C54 \\sim C55 \\sim C55A \\sim C54A \\sim N10A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(N10A)=
 Sof(H10A)=1-FVAR(1)
 Sof(N10)=Sof(H10)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10B,H10C), C11(H11A,H11B), C17(H17A,H17B), C32(H32A,H32B), C33(H33A,
 H33B), C39(H39A,H39B), C54(H54A,H54B), C55(H55A,H55B), C61(H61A,H61B),
 C55A(H55C,H55D), C54A(H54C,H54D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C28(H28), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  N10(H10), C46(H46), C48(H48), C50(H50), C63(H63), C64(H64), C65(H65),
 C66(H66), C67(H67), N10A(H10A)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              45907
_shelx_hkl_checksum              8357
_olex2_submission_special_instructions 'No special instructions were received'