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_1567846
_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         'C34 H32 F6 N6 O3'
_chemical_formula_sum            'C34 H32 F6 N6 O3'
_chemical_formula_weight         686.65
_chemical_melting_point          490
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.891(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9800(6)
_cell_length_b                   20.3627(6)
_cell_length_c                   16.4981(5)
_cell_measurement_reflns_used    7879
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4900
_cell_measurement_theta_min      3.6570
_cell_volume                     6368.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_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    -88.00 -42.00   1.00   12.50    --  -19.09 -37.00 -90.00   46
  2  \w    -94.00 -40.00   1.00   12.50    --  -19.09 178.00-180.00   54
  3  \w    -42.00  13.00   1.00   12.50    --  -19.09 -77.00 -60.00   55
  4  \w    -78.00  51.00   1.00   12.50    --  -19.09   0.00  90.00  129
  5  \w    -67.00 -26.00   1.00   12.50    --  -19.09 -37.00-150.00   41
  6  \w     37.00  80.00   1.00   12.50    --   20.18-178.00-150.00   43
  7  \w     -3.00  39.00   1.00   12.50    --   20.18  77.00  60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0216554000
_diffrn_orient_matrix_UB_12      -0.0231281000
_diffrn_orient_matrix_UB_13      -0.0191481000
_diffrn_orient_matrix_UB_21      0.0100423000
_diffrn_orient_matrix_UB_22      0.0245787000
_diffrn_orient_matrix_UB_23      -0.0276010000
_diffrn_orient_matrix_UB_31      0.0288174000
_diffrn_orient_matrix_UB_32      0.0087530000
_diffrn_orient_matrix_UB_33      0.0268539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.284
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (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    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             2848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7599
_refine_ls_number_restraints     203
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0335P)^2^+8.9127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5595
_reflns_number_total             7599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           s5847a
_cod_original_cell_volume        6368.2(3)
_cod_database_code               1567846
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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) groups
2. Restrained distances
 C13-N12 \\sim C13-N12A
 with sigma of 0.02
 N12-C20 \\sim N12A-C20
 with sigma of 0.02
 N12-C11 \\sim N12A-C11A
 with sigma of 0.02
 N9-C11 \\sim N9A-C11A
 with sigma of 0.04
 N9-C8 \\sim N9A-C8
 with sigma of 0.02
 N9-C10 \\sim N9A-C10A
 with sigma of 0.02
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 C20-C11 \\sim C20-C11A
 with sigma of 0.04
 C13-C11 \\sim C13-C11A
 with sigma of 0.04
 N12-C10 \\sim N12A-C10A
 with sigma of 0.04
 F31-C28 \\sim F31A-C28
 with sigma of 0.02
 F30-C28 \\sim F30A-C28
 with sigma of 0.02
 F29-C28 \\sim F29A-C28
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N12 \\sim N9 \\sim C11 \\sim C10 \\sim N12A \\sim C11A \\sim C10A \\sim N9A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
N12 \\sim N12A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
F29A \\sim F29 \\sim F30A \\sim F30 \\sim F31A \\sim F31: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 N15, C19, C32, C33, C34, C35, C36, C37
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H13C)=Sof(H13D)=Sof(N12A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C10A)=
 Sof(H10C)=Sof(H10D)=Sof(N9A)=Sof(H9A)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(N12)=Sof(N9)=Sof(H9)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
 Sof(F31A)=Sof(F29A)=Sof(F30A)=1-FVAR(2)
 Sof(F29)=Sof(F30)=Sof(F31)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C13(H13C,H13D), C19(H19A,H19B), C11(H11A,
 H11B), C10(H10A,H10B), C11A(H11C,H11D), C10A(H10C,H10D)
6.b Aromatic/amide H refined with riding coordinates:
 N18(H18), N22(H22), C2(H2), C43(H43), N7(H7), C4(H4), C6(H6), C39(H39),
 C48(H48), C41(H41), C37(H37), C42(H42), C40(H40), C45(H45), C35(H35), N9(H9),
 C46(H46), C49(H49), C36(H36), C47(H47), C33(H33), C34(H34), N9A(H9A)
;
_shelx_res_checksum              23900
_shelx_hkl_checksum              13877
_olex2_date_sample_data_collection 2021-06-07
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.503