Conformationally Adaptable Macrocyclic Receptors for Ditopic Anions: Analysis of Chelate Cooperativity in Aqueous Containing Media
Berry, Stuart N.; Qin, Lei; Lewis, William; Jolliffe, Katrina A.; Chemical Science  (2020) –; doi:10.1039/D0SC02533J

data_1558359
_publ_section_title
;
 Conformationally Adaptable Macrocyclic Receptors for Ditopic Anions:
 Analysis of Chelate Cooperativity in Aqueous Containing Media
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02533J
_journal_year                    2020
_chemical_formula_moiety
'2(C60 H70 N10 S4), 4(C16 H36 N), 2(C9 H14 O4)'
_chemical_formula_sum            'C206 H324 N24 O10 S10'
_chemical_formula_weight         3617.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-20 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.382(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.333(8)
_cell_length_b                   32.042(8)
_cell_length_c                   22.621(5)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.25
_cell_measurement_theta_min      2.17
_cell_volume                     21346(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Nonius APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'mirror optics'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2750
_diffrn_reflns_av_unetI/netI     0.3867
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            53500
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.147
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_min         0.939
_diffrn_source                   'rotating anode'
_diffrn_source_type              'FR591 rotating anode source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0751 before and 0.0546 after correction. The Ratio of minimum to maximum transmission is 0.9110. 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    1.126
_exptl_crystal_description       needle
_exptl_crystal_F_000             7872
_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1201
_refine_ls_number_reflns         18235
_refine_ls_number_restraints     2617
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.3840
_refine_ls_R_factor_gt           0.1359
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3209
_refine_ls_wR_factor_ref         0.4589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4231
_reflns_number_total             18235
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02533j2.cif
_cod_data_source_block           kaj19_s1742_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        21345(9)
_cod_database_code               1558359
_sydney_internal_submission_code kaj19_s1742
_sydney_internal_submission_date 2019-02-14
_sydney_internal_submission_number s1742
_sydney_internal_client_code     SNB
_sydney_internal_client_email    stuart.berry@sydney.edu.au
_sydney_internal_client_name     'Stuart Berry'
_sydney_internal_supervisor_code kaj
_sydney_internal_supervisor_name 'Kate Jolliffe'
_sydney_internal_collection_date 2019-02-21
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-02-25
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-02-25
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-02-26
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-02-27
_sydney_internal_check_user      wlew0588
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H87A-H92B
 -2.1 with sigma of 0.02
 H10G-H24E_$4
 -2.2 with sigma of 0.02
 N4-H4 = N5-H5 = N3-H3 = N2-H2 = N1-H1
 0.88 with sigma of 0.02
 N6-H6 = N7-H7A = N8-H8 = N9-H9 = N10-H10A
 0.88 with sigma of 0.02
 H9-H10A
 -2.1 with sigma of 0.02
 H87A-H92A
 -2.1 with sigma of 0.02
 H4-H5
 -2.1 with sigma of 0.02
 H7A-H8
 -2.1 with sigma of 0.02
 H10E-H26A
 -2.2 with sigma of 0.02
 H26F-H64B_$5
 -2.2 with sigma of 0.02
 H7-H26F
 -2.1 with sigma of 0.02
 H69A_$1-H68A
 -2.2 with sigma of 0.02
 H68B-H81B_$3
 -2.2 with sigma of 0.02
 H86B-H93A_$2
 -2.2 with sigma of 0.02
 H86A-H93A_$2
 -2.2 with sigma of 0.02
 C47-C46 = C51-C46 = C50-C49 = C49-C48 = C21-C16 = C17-C16 = C19-C18 = C20-C19
 = C51-C50 = C48-C47 = C18-C17 = C21-C20
 1.39 with sigma of 0.01
 O3-O4 \\sim O1-O2
 with sigma of 0.02
 C69-C70 \\sim C65-C64
 with sigma of 0.02
 C64-C64_$1 \\sim C69_$1-C69
 with sigma of 0.02
 C87-C91 \\sim C87-C99 \\sim C87-C95 \\sim C91-C95 \\sim C91-C99 \\sim C95-C99
\\sim C71-C75 \\sim C71-C79
 \\sim C71-C83 \\sim C75-C79 \\sim C75-C83 \\sim C79-C83
 with sigma of 0.02
 C76-C75 \\sim C80-C79 \\sim C84-C83 \\sim C72-C71 \\sim C88-C87 \\sim C92-C91
\\sim C99-C100 \\sim C96-C95
 with sigma of 0.02
 N11-C76 \\sim N11-C72 \\sim N11-C80 \\sim N11-C84 \\sim N12-C88 \\sim N12-C92
\\sim N12-C100 \\sim N12-C96
 with sigma of 0.02
 N12-C91 \\sim N12-C87 \\sim N12-C99 \\sim N12-C95 \\sim N11-C75 \\sim N11-C71
\\sim N11-C79 \\sim N11-C83
 with sigma of 0.02
 O2-C61 \\sim O1-C61 \\sim O4-C66 \\sim O3-C66
 with sigma of 0.02
 O3-C67 \\sim C67-O4 \\sim O1-C62 \\sim C62-O2
 with sigma of 0.02
 C68-C67 \\sim C63-C62
 with sigma of 0.02
 C69-C68 \\sim C64-C63
 with sigma of 0.02
 C67-C69 \\sim C62-C64
 with sigma of 0.02
 C63-C65 \\sim C68-C70
 with sigma of 0.02
 C62-C61 \\sim C67-C66
 with sigma of 0.02
 C66-C68 \\sim C61-C63
 with sigma of 0.02
 C68-C67 \\sim C69-C68 \\sim C70-C69 \\sim C63-C62 \\sim C64-C63 \\sim C65-C64
 with sigma of 0.02
 C25-C23 \\sim C25A-C23 \\sim C24-C23 \\sim C24A-C23 \\sim C26-C23 \\sim
C26A-C23 \\sim C30-C27 \\sim C28-
 C27 \\sim C29-C27 \\sim C58-C57 \\sim C60-C57 \\sim C59-C57 \\sim C56-C53
\\sim C55A-C53 \\sim C55-C53 ~
 C54A-C53 \\sim C54-C53 \\sim C56A-C53
 with sigma of 0.02
 C24-C25 \\sim C25-C26 \\sim C26-C24 \\sim C24A-C25A \\sim C25A-C26A \\sim
C26A-C24A \\sim C28-C29 ~
 C29-C30 \\sim C30-C28 \\sim C54-C55 \\sim C55-C56 \\sim C56-C54 \\sim
C54A-C55A \\sim C55A-C56A \\sim C56A-
 C54A \\sim C58-C59 \\sim C59-C60 \\sim C60-C58
 with sigma of 0.02
 C6-C24 \\sim C6-C25 \\sim C6-C26 \\sim C6-C24A \\sim C6-C25A \\sim C6-C26A
\\sim C11-C28 \\sim C11-C29 ~
 C11-C30 \\sim C36-C54 \\sim C36-C55 \\sim C36-C56 \\sim C36-C54A \\sim
C36-C55A \\sim C36-C56A \\sim C41-
 C58 \\sim C41-C59 \\sim C41-C60
 with sigma of 0.02
 C75-C77 \\sim C79-C81 \\sim C83-C85 \\sim C71-C73 \\sim C87-C89 \\sim C91-C93
\\sim C99-C101 \\sim C95-C97
 with sigma of 0.02
 C89-C88 \\sim C97-C96 \\sim C101-C100 \\sim C93-C92 \\sim C77-C76 \\sim
C81-C80 \\sim C85-C84 \\sim C73-C72
 with sigma of 0.02
 C74-C73 \\sim C86-C85 \\sim C82-C81 \\sim C78-C77 \\sim C98-C97 \\sim C90-C89
\\sim C94-C93 \\sim C102-C101
 with sigma of 0.01
 C96-C98 \\sim C88-C90 \\sim C100-C102 \\sim C94-C92 \\sim C80-C82 \\sim
C78-C76 \\sim C72-C74 \\sim C84-C86
 with sigma of 0.02
 C20-C16 \\sim C16-C18 \\sim C21-C19 \\sim C19-C17 \\sim C47-C49 \\sim C49-C51
\\sim C48-C46 \\sim C46-C50
 \\sim C48-C50 \\sim C51-C47 \\sim C17-C21 \\sim C20-C18
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
 Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=Sof(C55A)=Sof(H55D)=Sof(H55E)=
 Sof(H55F)=Sof(C56A)=Sof(H56D)=Sof(H56E)=Sof(H56F)=1-FVAR(2)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=
 Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=FVAR(2)
 Fixed Sof: H65A(0.5) H65B(0.5) H70A(0.5) H70B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B), C45(H45A,H45B), C52(H52A,H52B), C87(H87A,
 H87B), C88(H88A,H88B), C89(H89A,H89B), C91(H91A,H91B), C92(H92A,H92B),
 C93(H93A,H93B), C95(H95A,H95B), C96(H96A,H96B), C97(H97A,H97B), C99(H99A,H99B),
  C100(H10B,H10C), C101(H10D,H10E), C71(H71A,H71B), C72(H72A,H72B), C73(H73A,
 H73B), C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B), C79(H79A,H79B),
 C80(H80A,H80B), C81(H81A,H81B), C83(H83A,H83B), C84(H84A,H84B), C85(H85A,H85B),
  C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C67(H67A,
 H67B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,H70B)
6.b Me refined with riding coordinates:
 C24(H24A,H24B,H24C), C54A(H54D,H54E,H54F)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C7(H7), C10(H10), C12(H12), C17(H17), C18(H18), C20(H20), C21(H21),
 C35(H35), C37(H37), C40(H40), C42(H42), C47(H47), C48(H48), C50(H50), C51(H51)
6.d Idealised Me refined as rotating group:
 C24A(H24D,H24E,H24F), C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C26(H26A,
 H26B,H26C), C26A(H26D,H26E,H26F), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C55A(H55D,H55E,
 H55F), C56(H56A,H56B,H56C), C56A(H56D,H56E,H56F), C58(H58A,H58B,H58C),
 C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C90(H90A,H90B,H90C), C94(H94A,H94B,
 H94C), C98(H98A,H98B,H98C), C102(H10F,H10G,H10H), C74(H74A,H74B,H74C),
 C78(H78A,H78B,H78C), C82(H82A,H82B,H82C), C86(H86A,H86B,H86C)
;
_shelx_res_checksum              88257
_shelx_fab_checksum              62881
_olex2_date_sample_data_collection 2019-02-21
_olex2_date_sample_submission    2019-02-14
_olex2_exptl_crystal_mounting_method 'in paratone-N on a micromount'
_olex2_submission_original_sample_id 'SB-1-100 plus TBA(2) Azelate'
_olex2_submission_special_instructions 'No special instructions were received'