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_1567855
_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         'C28 H34 N6 O3'
_chemical_formula_sum            'C28 H34 N6 O3'
_chemical_formula_weight         502.61
_chemical_melting_point          541
_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             2021-04-28
_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                 92.0060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.90610(10)
_cell_length_b                   28.6533(4)
_cell_length_c                   15.5357(2)
_cell_measurement_reflns_used    12481
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1970
_cell_measurement_theta_min      3.0330
_cell_volume                     2627.48(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    108.00 133.00   1.00    0.34    --   43.54  59.00  26.00   25
  2  \w    -30.00  -4.00   1.00    0.34    --   43.54  59.00  26.00   26
  3  \w     47.00 195.00   1.00    0.34    --  108.20  59.00  26.00  148
  4  \w     65.00 129.00   1.00    0.34    --   43.54  10.00   0.00   64
  5  \w    -45.00 133.00   1.00    0.34    --   43.54  10.00-120.00  178
  6  \w     35.00  61.00   1.00    0.34    --   43.54  10.00   0.00   26
  7  \w    -43.00 134.00   1.00    0.34    --   46.06  60.00-180.00  177
  8  \w     86.00 134.00   1.00    0.34    --   46.06  30.00  30.00   48
  9  \w     22.00  47.00   1.00    0.34    --   46.06  59.00  26.00   25
 10  \w     22.00  85.00   1.00    0.34    --  108.20  40.00 -30.00   63
 11  \w    112.00 198.00   1.00    0.34    --  108.20   0.00   0.00   86
 12  \w     21.00 128.00   1.00    0.34    --  108.20   0.00-180.00  107
 13  \w    120.00 147.00   1.00    0.34    --  108.20  50.00  90.00   27
 14  \w     54.00 196.00   1.00    0.34    --  108.20  40.00-180.00  142
 15  \w     38.00  64.00   1.00    0.34    --  108.20  10.00 -30.00   26
 16  \w     20.00  94.00   1.00    0.34    --  108.20  50.00  90.00   74
 17  \w     88.00 113.00   1.00    0.34    --  108.20  40.00 -30.00   25
 18  \w     22.00  49.00   1.00    0.34    --  108.20   0.00   0.00   27
 19  \w    107.00 160.00   1.00    0.34    --  108.20  10.00  90.00   53
 20  \w    104.00 197.00   1.00    0.34    --  108.20  50.00 -60.00   93
 21  \w     25.00  51.00   1.00    0.34    --  108.20  10.00  90.00   26
 22  \w    137.00 182.00   1.00    0.34    --  108.20  40.00 -30.00   45
 23  \w     72.00 151.00   1.00    0.34    --  108.20  50.00  60.00   79
 24  \w    166.00 197.00   1.00    0.34    --  108.20  50.00  60.00   31
 25  \w     20.00  46.00   1.00    0.34    --  108.20  40.00-180.00   26
 26  \w     20.00  66.00   1.00    0.34    --  108.20  50.00 -60.00   46
 27  \w     23.00  50.00   1.00    0.34    --  108.20  10.00 -60.00   27
 28  \w    132.00 170.00   1.00    0.34    --  108.20   0.00-180.00   38
 29  \w    150.00 175.00   1.00    0.34    --  108.20  10.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1954321000
_diffrn_orient_matrix_UB_12      -0.0203625000
_diffrn_orient_matrix_UB_13      -0.0565987000
_diffrn_orient_matrix_UB_21      -0.1516517000
_diffrn_orient_matrix_UB_22      0.0414217000
_diffrn_orient_matrix_UB_23      0.0240240000
_diffrn_orient_matrix_UB_31      0.0838208000
_diffrn_orient_matrix_UB_32      0.0275657000
_diffrn_orient_matrix_UB_33      -0.0777953000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.365
_diffrn_reflns_theta_min         3.085
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.106a (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    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00131(14)
_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   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0404P)^2^+0.7927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4723
_reflns_number_total             5438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           s5814l_auto
_cod_database_code               1567855
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H6 of N6, H5 of N5, H4 of N4, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H3 of N3
2.a Riding coordinates:
 N5(H5), N4(H4), N3(H3), N6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B), C13(H13A,H13B), C2(H2A,H2B), C3(H3A,H3B),
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6A), C7(H7), C8(H8),
 C9(H9), C10(H10), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              58523
_shelx_hkl_checksum              62766
_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 1.602
_oxdiff_exptl_absorpt_empirical_full_min 0.679