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_1567844
_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         '1(C32 H36 F6 N6 O3)'
_chemical_formula_sum            'C32 H36 F6 N6 O3'
_chemical_formula_weight         666.67
_chemical_melting_point          448
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-01-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                92.4420(10)
_cell_angle_beta                 113.7000(10)
_cell_angle_gamma                112.8530(10)
_cell_formula_units_Z            4
_cell_length_a                   14.5061(3)
_cell_length_b                   15.7206(4)
_cell_length_c                   17.2781(4)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.64
_cell_measurement_theta_min      3.65
_cell_volume                     3231.16(14)
_computing_cell_refinement       'SAINT v8.39.0 (Bruker, 2018)'
_computing_data_collection       'Bruker SC-XRD Suite'
_computing_data_reduction        'SAINT v8.39.0 (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON III C7'
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Venture dual source kappa CPAD'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            67927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.684
_diffrn_reflns_theta_min         2.874
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\uS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.5074.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1053
_refine_ls_number_reflns         13186
_refine_ls_number_restraints     750
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0498P)^2^+1.2939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12198
_reflns_number_total             13186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           g49
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3231.16(13)
_cod_database_code               1567844
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.720
_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,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N10, N10A}
3. Restrained distances
 N8-C41 = N8B-C41 = N8A-C41 = N11-C53A = N11-C53B = N11-C53 = N9A-C53A = N9B-
 C53B = N9-C53
 1.36 with sigma of 0.01
 N11-C54 = N11-C54A
 1.45 with sigma of 0.01
 N8-C42 = N8B-C42B = N8A-C42A = N9A-C43A = N9B-C43B = N9-C43 = N9A-C44A = N9B-
 C44B = N9-C44 = N10A-C45A = N10-C45 = N10B-C45B = N9A-C53A = N9B-C53B = N9-C53
 1.45 with sigma of 0.005
 C55-C54 = C55A-C54A = C56A-C55A = C56-C55 = C57A-C56A = C57-C56
 1.52 with sigma of 0.01
 C43A-C42A = C43B-C42B = C43-C42 = C45A-C44A = C45B-C44B = C45-C44
 1.53 with sigma of 0.01
 O5A-C53A = O5B-C53B = O5-C53
 1.2 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C42 \\sim C42A \\sim C42B \\sim C43 \\sim C43A \\sim C43B \\sim C44 \\sim C44A
\\sim C44B \\sim C45 \\sim C45A \\sim C45B \\sim C53 \\sim C53A \\sim C53B
\\sim C54 \\sim C54A \\sim C55 \\sim C55A \\sim C56 \\sim C56A \\sim C57 \\sim
C57A \\sim N8 \\sim N8A \\sim N8B \\sim N9 \\sim N9A \\sim N9B \\sim N10 \\sim
N10A \\sim N10B \\sim N11 \\sim O5 \\sim O5A \\sim O5B: within 2A with sigma of
0.003 and sigma for terminal atoms of 0.006 within 2A
Uanis(C53B) = Uanis(C53) = Uanis(C53A)
Uanis(N10B) = Uanis(N10) = Uanis(N10A)
5. Others
 1*[Sof(C42)+Sof(H42A)+Sof(H42B)+Sof(C43)+Sof(H43A)+Sof(H43B)+Sof(C44)+
 Sof(H44A)+Sof(H44B)+Sof(C45)+Sof(H45A)+Sof(H45B)+Sof(H46A)+Sof(H46B)+Sof(C53)+
 Sof(N8)+Sof(H8)+Sof(N9)+Sof(N10)+Sof(O5)]+1*[Sof(C42B)+Sof(H42E)+Sof(H42F)+
 Sof(C43B)+Sof(H43E)+Sof(H43F)+Sof(C44B)+Sof(H44E)+Sof(H44F)+Sof(C45B)+
 Sof(H45E)+Sof(H45F)+Sof(H46E)+Sof(H46F)+Sof(C53B)+Sof(N8B)+Sof(H8B)+Sof(N9B)+
 Sof(N10B)+Sof(O5B)]+1*[Sof(C42A)+Sof(H42C)+Sof(H42D)+Sof(C43A)+Sof(H43C)+
 Sof(H43D)+Sof(C44A)+Sof(H44C)+Sof(H44D)+Sof(C45A)+Sof(H45C)+Sof(H45D)+
 Sof(H46C)+Sof(H46D)+Sof(C53A)+Sof(N8A)+Sof(H8A)+Sof(N9A)+Sof(N10A)+Sof(O5A)]=1
 with esd of 0
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=
 Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H46A)=Sof(H46B)=Sof(C53)=Sof(N8)=
 Sof(H8)=Sof(N9)=Sof(N10)=Sof(O5)=FVAR(1)
 Sof(C42B)=Sof(H42E)=Sof(H42F)=Sof(C43B)=Sof(H43E)=Sof(H43F)=Sof(C44B)=
 Sof(H44E)=Sof(H44F)=Sof(C45B)=Sof(H45E)=Sof(H45F)=Sof(H46E)=Sof(H46F)=
 Sof(C53B)=Sof(N8B)=Sof(H8B)=Sof(N9B)=Sof(N10B)=Sof(O5B)=FVAR(2)
 Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=Sof(C44A)=
 Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(H46C)=Sof(H46D)=
 Sof(C53A)=Sof(N8A)=Sof(H8A)=Sof(N9A)=Sof(N10A)=Sof(O5A)=FVAR(3)
 Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C56A)=
 Sof(H56C)=Sof(H56D)=Sof(C57A)=Sof(H57D)=Sof(H57E)=Sof(H57F)=1-FVAR(4)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=
 Sof(H56B)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C42(H42A,H42B),
 C42A(H42C,H42D), C42B(H42E,H42F), C43(H43A,H43B), C43A(H43C,H43D), C43B(H43E,
 H43F), C44(H44A,H44B), C44A(H44C,H44D), C44B(H44E,H44F), C45(H45A,H45B),
 C45A(H45C,H45D), C45B(H45E,H45F), C46(H46A,H46B), C46(H46C,H46D), C46(H46E,
 H46F), C54(H54A,H54B), C54A(H54C,H54D), C55(H55A,H55B), C55A(H55C,H55D),
 C56(H56A,H56B), C56A(H56C,H56D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C36(H36), C38(H38),
  C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C60(H60), C61(H61),
 C62(H62), C63(H63), C64(H64), N8(H8), N8A(H8A), N8B(H8B)
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C57(H57A,H57B,H57C), C57A(H57D,H57E,H57F)
;
_shelx_res_checksum              53738
_shelx_hkl_checksum              6374
_olex2_date_sample_data_collection 2022-01-12
_olex2_date_sample_submission    2022-01-11
_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'