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_1567854
_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 H42 F12 N8 O4'
_chemical_formula_sum            'C34 H42 F12 N8 O4'
_chemical_formula_weight         854.75
_chemical_melting_point          467.0(10)
_chemical_name_systematic
1,1'-(ethane-1,2-diyl)bis(1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-butylurea)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-01
_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                90
_cell_angle_beta                 95.262(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   16.7460(8)
_cell_length_b                   15.9603(8)
_cell_length_c                   22.0769(10)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.26
_cell_measurement_theta_min      2.25
_cell_volume                     5875.7(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            44009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.221
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0674 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.8085. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             2652
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     907
_refine_ls_number_reflns         10759
_refine_ls_number_restraints     477
_refine_ls_restrained_S_all      1.430
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0461P)^2^+3.9872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7274
_reflns_number_total             10759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testm1_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '466-468' was changed to
'467.0(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               1567854
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Restrained distances
 F1A-C8 \\sim F2-C8 \\sim F2A-C8 \\sim F3-C8 \\sim F3A-C8 \\sim F1-C8 \\sim
F18-C43 \\sim F18A-C43 \\sim F16-
 C43 \\sim F16A-C43 \\sim F17-C43 \\sim F17A-C43 \\sim F13-C42 \\sim F13A-C42
\\sim F14-C42 \\sim F14A-C42
 \\sim F15-C42 \\sim F15A-C42
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim C8 \\sim F2A \\sim F3A \\sim F1A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F16 \\sim F17 \\sim F18 \\sim C43 \\sim F16A \\sim F17A \\sim F18A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F13 \\sim F14 \\sim F15 \\sim C42 \\sim F15A \\sim F13A \\sim F14A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(F1) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(F18) \\sim Ueq, Uanis(F18A) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F16A)
\\sim Ueq, Uanis(F17A) \\sim Ueq, Uanis(F17) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(F14) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F15A)
\\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F13A) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
3. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(2)
 Sof(F16)=Sof(F17)=Sof(F18)=FVAR(2)
 Sof(F15A)=Sof(F13A)=Sof(F14A)=1-FVAR(3)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B), C44(H44A,H44B), C45(H45A,H45B),
  C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C51(H51A,H51B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7A), C28(H28), C30(H30), C32(H32), C37(H37), C39(H39),
 C41(H41)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              68882
_shelx_hkl_checksum              98446
_olex2_submission_special_instructions 'No special instructions were received'