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_1567853
_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         'C27 H42 F6 N6 O3'
_chemical_formula_sum            'C27 H42 F6 N6 O3'
_chemical_formula_weight         612.66
_chemical_melting_point          422.0(10)
_chemical_name_systematic
1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-hexyl-1-(2-(3-hexylureido)ethyl)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   geom
_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                104.669(9)
_cell_angle_beta                 93.989(10)
_cell_angle_gamma                99.942(10)
_cell_formula_units_Z            4
_cell_length_a                   10.2341(13)
_cell_length_b                   13.1050(13)
_cell_length_c                   24.026(3)
_cell_measurement_reflns_used    2366
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      24.8220
_cell_measurement_theta_min      3.6210
_cell_volume                     3048.7(6)
_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(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -32.00  12.00   1.00    5.00    --  -18.04 -77.00-150.00   44
  2  \w    -42.00  12.00   1.00    5.00    --  -18.04 -77.00  90.00   54
  3  \w     39.00  92.00   1.00    5.00    --   19.45 178.00 -60.00   53
  4  \w    -48.00  45.00   1.00    5.00    --   19.45 -37.00 -90.00   93
  5  \w     -6.00  90.00   1.00    5.00    --   19.45  37.00  90.00   96
;
_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      -0.0177469000
_diffrn_orient_matrix_UB_12      -0.0389490000
_diffrn_orient_matrix_UB_13      -0.0271996000
_diffrn_orient_matrix_UB_21      -0.0028023000
_diffrn_orient_matrix_UB_22      -0.0417100000
_diffrn_orient_matrix_UB_23      0.0140574000
_diffrn_orient_matrix_UB_31      -0.0685517000
_diffrn_orient_matrix_UB_32      0.0001567000
_diffrn_orient_matrix_UB_33      0.0026893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1873
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16786
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.278
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86702
_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    1.335
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         16786
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      0.816
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0459P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6800
_reflns_number_total             16786
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 3.5200\% 
around [0.20 0.83 -0.51] (reciprocal) or [0.51 0.86 -0.01] (direct)
;
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           s5691a_twin1_hklf4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '421-423' was changed to
'422.0(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_original_cell_volume        3048.6(6)
_cod_database_code               1567853
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.57899
 0.42101
2. Uiso/Uaniso restraints and constraints
C35 \\sim C32 \\sim C31 \\sim C33 \\sim C34: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
N7 \\sim C5 \\sim C3 \\sim N4: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
C8 \\sim N7 \\sim C5 \\sim N4 \\sim C3 \\sim C2: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004 within 2A
N1 \\sim C36 \\sim N38 \\sim C39 \\sim C40 \\sim C41: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.004 within 2A
O126 \\sim C125 \\sim N127 \\sim C128 \\sim N124: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004 within 2A
C35 \\sim C32 \\sim C33 \\sim C31: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
Uanis(N4) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(N38) \\sim Ueq, Uanis(N1) \\sim
Ueq, Uanis(N24) \\sim Ueq, Uanis(N104) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(C113) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Others
 Sof(H30C)=Sof(H30D)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C33)=Sof(H33A)=
 Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=1-FVAR(1)
 Sof(H30A)=Sof(H30B)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(C31)=Sof(H31A)=Sof(H31B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C103(H10A,H10B), C2(H2A,H2B), C129(H12A,H12B), C102(H10C,H10D),
 C23(H23A,H23B), C123(H12C,H12D), C22(H22A,H22B), C39(H39A,H39B), C28(H28A,
 H28B), C128(H12E,H12F), C137(H13A,H13B), C138(H13C,H13D), C40(H40A,H40B),
 C41(H41A,H41B), C139(H13E,H13F), C131(H13G,H13H), C43(H43A,H43B), C140(H14A,
 H14B), C130(H13I,H13J), C132(H13N,H13O), C122(H12G,H12H), C42(H42A,H42B),
 C29(H29A,H29B), C30(H30A,H30B), C30(H30C,H30D), C141(H14F,H14G), C32(H32A,
 H32B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B)
4.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N24(H24), N107(H107), N124(H124), N38(H38), N104(H104), N4(H4),
 N127(H127), N136(H136), N27(H27), C9(H9), C113(H113), C13(H13), C11(H11),
 C111(H111), C109(H109)
4.c Idealised Me refined as rotating group:
 C133(H13K,H13L,H13M), C142(H14C,H14D,H14E), C44(H44A,H44B,H44C), C35(H35A,
 H35B,H35C), C35(H35D,H35E,H35F)
;
_shelx_res_checksum              39511
_shelx_hkl_checksum              36391
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.616
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2