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_1567851
_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         'C50 H50 F12 N10 O8, 2(C2 H3 N)'
_chemical_formula_sum            'C54 H56 F12 N12 O8'
_chemical_formula_weight         1229.10
_chemical_melting_point          409.0(10)
_chemical_name_systematic
1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-1-(2-(1-(2-(1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-(4-methoxyphenyl)ureido)ethyl)-3-(4-methoxyphenyl)ureido)ethyl)-3-(4-methoxyphenyl)urea
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_audit_update_record
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                71.522(5)
_cell_angle_beta                 75.149(5)
_cell_angle_gamma                81.278(5)
_cell_formula_units_Z            2
_cell_length_a                   11.6563(7)
_cell_length_b                   15.0421(8)
_cell_length_c                   17.5808(9)
_cell_measurement_reflns_used    4070
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      25.1910
_cell_measurement_theta_min      3.5070
_cell_volume                     2817.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     23.00  73.00   1.00    5.00    --   19.45  57.00  30.00   50
  2  \w    -49.00  41.00   1.00    5.00    --   19.45 -57.00  90.00   90
  3  \w    -11.00  15.00   1.00    5.00    --   19.45  77.00 120.00   26
  4  \w     -1.00  92.00   1.00    5.00    --   19.45  37.00-120.00   93
  5  \w     -6.00  90.00   1.00    5.00    --   19.45  37.00 -30.00   96
  6  \w     -6.00  32.00   1.00    5.00    --   19.45  77.00   0.00   38
  7  \w     32.00  61.00   1.00    5.00    --   19.45 -99.00-120.00   29
;
_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      -0.0628435000
_diffrn_orient_matrix_UB_12      0.0038528000
_diffrn_orient_matrix_UB_13      0.0056892000
_diffrn_orient_matrix_UB_21      0.0056493000
_diffrn_orient_matrix_UB_22      0.0198801000
_diffrn_orient_matrix_UB_23      -0.0430230000
_diffrn_orient_matrix_UB_31      0.0024803000
_diffrn_orient_matrix_UB_32      -0.0455618000
_diffrn_orient_matrix_UB_33      -0.0044026000
_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  0.0481
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.404
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.449
_exptl_crystal_description       plank
_exptl_crystal_F_000             1272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     853
_refine_ls_number_reflns         10289
_refine_ls_number_restraints     406
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0245P)^2^+1.0627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6532
_reflns_number_total             10289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           s5690a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '408-410' was changed to
'409.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1567851
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.959
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Restrained distances
 O14-C1Q \\sim O14A-C1
 with sigma of 0.02
 N9-C26 \\sim N9A-C26A
 with sigma of 0.04
 O16-C27 \\sim O16A-C27A
 with sigma of 0.02
 N1-C1Q \\sim N1-C1
 with sigma of 0.02
 N9-C1Q \\sim N9A-C1
 with sigma of 0.02
 N5-C25 \\sim N5A-C25A
 with sigma of 0.04
 N9-C1T \\sim N9A-C1T
 with sigma of 0.02
 C26-C27 \\sim C26A-C27A
 with sigma of 0.04
 N9-C25 \\sim N9A-C25A
 with sigma of 0.02
 C1Q-C25 \\sim C1-C25A
 with sigma of 0.04
 C1T-C25 \\sim C1T-C25A
 with sigma of 0.04
 N4-C27 \\sim N4-C27A
 with sigma of 0.02
 N5-C26 \\sim N5A-C26A
 with sigma of 0.02
 N5-C27 \\sim N5A-C27A
 with sigma of 0.02
 N1-N9 \\sim N1-N9A
 with sigma of 0.04
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C1Q-C1T \\sim C1-C1T
 with sigma of 0.04
 N4-N5 \\sim N4-N5A
 with sigma of 0.04
 O14-N1 \\sim O14A-N1
 with sigma of 0.04
 O14-N9 \\sim O14A-N9A
 with sigma of 0.04
 O16-N4 \\sim O16A-N4
 with sigma of 0.04
 O16-N5 \\sim O16A-N5A
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
O14 \\sim O16 \\sim N1 \\sim N9 \\sim C1Q \\sim C1T \\sim N4 \\sim N5 \\sim C25
\\sim C26 \\sim C27 \\sim C27A \\sim O16A \\sim N5A \\sim C26A \\sim C25A \\sim
N9A \\sim C1 \\sim O14A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O16A \\sim O16: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C27A \\sim C27: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C25 \\sim C25A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C1 \\sim C1Q: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
3. Rigid body (RIGU) restrains
 O14, O16, N1, N9, C1Q, C1T, N4, N5, C25, C26, C27, C27A, O16A, N5A, C26A,
 C25A, N9A, C1, O14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H1B)=Sof(H1TC)=Sof(H1TD)=Sof(H4B)=Sof(C27A)=Sof(O16A)=Sof(N5A)=Sof(H5A)=
 Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(N9A)=Sof(C1)=
 Sof(O14A)=1-FVAR(1)
 Sof(O14)=Sof(O16)=Sof(H1A)=Sof(N9)=Sof(C1Q)=Sof(H1TA)=Sof(H1TB)=Sof(H4A)=
 Sof(N5)=Sof(H5)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=FVAR(1)
5.a Riding coordinates:
 N4(H4B)
5.b Secondary CH2 refined with riding coordinates:
 C1H(H1HA,H1HB), C1L(H1LA,H1LB), C1T(H1TA,H1TB), C1T(H1TC,H1TD), C1Z(H1ZA,
 H1ZB), C21(H21A,H21B), C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B),
 C26A(H26C,H26D), C25A(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N12(H12), N1(H1A), N1(H1B), N6(H6), C1D(H1D), C1E(H1E),
 C1F(H1F), C1I(H1I), C1J(H1J), C1K(H1K), C1M(H1M), C1N(H1N), C1O(H1O), C1P(H1P),
  C1R(H1R), C1W(H1W), C1X(H1X), N4(H4A), N5(H5), C8(H8), C9(H9), C11(H11),
 C15(H15), C17(H17), N5A(H5A)
5.d Idealised Me refined as rotating group:
 C2B(H2BA,H2BB,H2BC), C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C2C(H2CA,H2CB,
 H2CC), C2D(H2DA,H2DB,H2DC)
;
_shelx_res_checksum              43210
_shelx_hkl_checksum              45148
_olex2_date_sample_data_collection 2020-11-05
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.765