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_1567858
_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         'C20 H20 F6 N4 O2'
_chemical_formula_sum            'C20 H20 F6 N4 O2'
_chemical_formula_weight         462.40
_chemical_melting_point          465
_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             2022-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-21 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.558(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7401(12)
_cell_length_b                   14.0361(11)
_cell_length_c                   11.5499(10)
_cell_measurement_reflns_used    9699
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.754
_cell_measurement_theta_min      2.409
_cell_volume                     2041.8(3)
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            59432
_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         25.676
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\uS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1486 before and 0.0862 after correction.
The Ratio of minimum to maximum transmission is 0.7127.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.383
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0374P)^2^+1.3333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2816
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           g32a
_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_database_code               1567858
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Restrained distances
 F2B-C7 \\sim F2-C7 \\sim F2A-C7 \\sim F1A-C7 \\sim F1-C7 \\sim F1B-C7 \\sim
F3A-C7 \\sim F3-C7 \\sim F3B-C7
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A \\sim
F1B-F2B \\sim F1B-F3B \\sim F2B-
 F3B
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
F1B \\sim F1 \\sim F1A \\sim F2A \\sim F2B \\sim F2 \\sim F3 \\sim F3A \\sim
F3B: within 2A with sigma of 0.003 and sigma for terminal atoms of 0.006 within
2A
Uanis(F1B) = Uanis(F1) = Uanis(F1A)
Uanis(F3) = Uanis(F3A) = Uanis(F3B)
Uanis(F2) = Uanis(F2B) = Uanis(F2A)
3. Others
 1*[Sof(F1A)+Sof(F3A)+Sof(F2A)]+1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F2B)+
 Sof(F1B)+Sof(F3B)]=1 with esd of 0
 Sof(F1A)=Sof(F3A)=Sof(F2A)=FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
 Sof(F2B)=Sof(F1B)=Sof(F3B)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B), C10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C3(H3), C1(H1A), C15(H15), C14(H14), C16(H16), C5(H5), C18(H18)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              8266
_shelx_hkl_checksum              89547
_olex2_submission_special_instructions 'No special instructions were received'