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_1567857
_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         'C17 H22 F6 N4 O2'
_chemical_formula_sum            'C17 H22 F6 N4 O2'
_chemical_formula_weight         428.38
_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             2022-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-21 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.437(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6426(4)
_cell_length_b                   11.0107(4)
_cell_length_c                   16.8030(5)
_cell_measurement_reflns_used    5217
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.7890
_cell_measurement_theta_min      3.9680
_cell_volume                     2043.47(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     21.00  47.00   1.00    1.00    --   46.06  20.00 150.00   26
  2  \w     84.00 133.00   1.00    1.00    --   46.06  20.00 150.00   49
  3  \w    -42.00 134.00   1.00    1.00    --   46.06  60.00 120.00  176
  4  \w    -33.00  -6.00   1.00    1.00    --   46.06  20.00 150.00   27
  5  \w     61.00  86.00   1.00    1.00    --   46.06   0.00-180.00   25
  6  \w     19.00  59.00   1.00    1.00    --  108.20  50.00-150.00   40
  7  \w     56.00 159.00   1.00    1.00    --  108.20  50.00-120.00  103
  8  \w     89.00 116.00   1.00    1.00    --  108.20  40.00-180.00   27
  9  \w     96.00 167.00   1.00    1.00    --  108.20  50.00 150.00   71
 10  \w    146.00 198.00   1.00    1.00    --  108.20  10.00  30.00   52
 11  \w     27.00  74.00   1.00    1.00    --  108.20  50.00  90.00   47
 12  \w    107.00 193.00   1.00    1.00    --  108.20  50.00  90.00   86
 13  \w     47.00  73.00   1.00    1.00    --  108.20  50.00 150.00   26
 14  \w     79.00 105.00   1.00    1.00    --  108.20  50.00-150.00   26
 15  \w     20.00  51.00   1.00    1.00    --  108.20  10.00  30.00   31
 16  \w     19.00 156.00   1.00    1.00    --  108.20  50.00 -90.00  137
 17  \w    143.00 169.00   1.00    1.00    --  108.20  50.00-150.00   26
 18  \w    138.00 165.00   1.00    1.00    --  108.20  40.00-180.00   27
 19  \w     28.00  70.00   1.00    1.00    --  108.20  40.00-180.00   42
 20  \w    129.00 166.00   1.00    1.00    --  108.20  50.00-180.00   37
 21  \w    132.00 198.00   1.00    1.00    --  108.20  20.00  30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12890
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.085
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.377
_exptl_crystal_size_min          0.328
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.275
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0628P)^2^+0.7323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3124
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           s5784l_auto
_cod_original_cell_volume        2043.46(12)
_cod_database_code               1567857
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.706
_shelx_estimated_absorpt_t_min   0.568
_olex2_refinement_description
;
1. Restrained distances
 F2B-C7 \\sim F3-C7 \\sim F3A-C7 \\sim F2B-C7 \\sim F1-C7 \\sim F1A-C7 \\sim
F2B-C7 \\sim F2-C7 \\sim F2A-C7
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A \\sim
F1B-F2B \\sim F1B-F3B \\sim F2B-
 F3B
 with sigma of 0.02
 F5-C8 \\sim F5A-C8 \\sim F6-C8 \\sim F6A-C8 \\sim F4-C8 \\sim F4A-C8
 with sigma of 0.01
 F4-F5 \\sim F4-F6 \\sim F5-F6 \\sim F4A-F5A \\sim F4A-F6A \\sim F5A-F6A
 with sigma of 0.02
 N1-H1 \\sim N2-H2 \\sim N4-H4
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F2B) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq,
Uanis(F1B) \\sim Ueq, Uanis(F3B) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F6)
\\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F4) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(F3) = Uanis(F3A) = Uanis(F1B)
Uanis(F4) = Uanis(F4A)
3. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F2)+Sof(F1)+Sof(F3)]+1*[Sof(F2B)+
 Sof(F1B)+Sof(F3B)]=1 with esd of 0
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(2)
 Sof(F2B)=Sof(F1B)=Sof(F3B)=FVAR(3)
 Sof(F6)=Sof(F4)=Sof(F5)=1-FVAR(4)
 Sof(F6A)=Sof(F4A)=Sof(F5A)=FVAR(4)
4.a Ternary CH refined with riding coordinates:
 C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C16(H16A,H16B), C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C1(H1A)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              83168
_shelx_hkl_checksum              89790
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;