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_1558358
_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         'C60 H70 N10 S4, C6 H8 O4, 2(C16 H36 N)'
_chemical_formula_sum            'C98 H150 N12 O4 S4'
_chemical_formula_weight         1688.53
_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     iterative
_audit_creation_date             2019-03-11
_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                87.790(3)
_cell_angle_beta                 79.140(4)
_cell_angle_gamma                67.556(5)
_cell_formula_units_Z            2
_cell_length_a                   14.5133(7)
_cell_length_b                   16.3538(7)
_cell_length_c                   22.1946(8)
_cell_measurement_reflns_used    11066
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4050
_cell_measurement_theta_min      3.6050
_cell_volume                     4778.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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    -74.00  46.00   1.00   30.00    --  -38.00  77.00  60.00  120
  2  \w    -71.00  40.00   1.00   30.00    --  -38.00  57.00 -90.00  111
  3  \w   -130.00  54.00   1.00   30.00    --  -38.00   0.00 240.00  184
  4  \w     55.00 129.00   1.00   30.00    --   38.00-178.00  60.00   74
  5  \w     55.00 129.00   1.00   30.00    --   38.00-178.00-120.00   74
  6  \w     26.00  91.00   1.00  120.00    --  107.26 -30.00  30.00   65
  7  \w     26.00  91.00   1.00  120.00    --  107.26 -30.00 150.00   65
  8  \w     21.00 110.00   1.00  120.00    --  107.26 -95.00 -30.00   89
  9  \w     26.00  91.00   1.00  120.00    --  107.26 -30.00  90.00   65
 10  \w     26.00 112.00   1.00  120.00    --  107.26-111.00-180.00   86
 11  \w    100.00 178.00   1.00  120.00    --  107.26 111.00-180.00   78
 12  \w     26.00 112.00   1.00  120.00    --  107.26-111.00 -90.00   86
 13  \f     10.00 117.00   1.00  120.00  40.00 107.26   0.00    --   107
 14  \w     29.00  98.00   1.00  120.00    --  107.26 -45.00 -60.00   69
 15  \w     26.00 112.00   1.00  120.00    --  107.26-111.00  30.00   86
 16  \w     29.00 140.00   1.00  120.00    --  107.26 -61.00-120.00  111
 17  \w     76.00 178.00   1.00  120.00    --  107.26  45.00-150.00  102
 18  \w     26.00  91.00   1.00  120.00    --  107.26 -30.00-150.00   65
 19  \w     26.00 112.00   1.00  120.00    --  107.26-111.00 120.00   86
 20  \w     23.00 143.00   1.00  120.00    --  107.26 -77.00 120.00  120
 21  \w    100.00 178.00   1.00  120.00    --  107.26  80.00  -9.00   78
 22  \w   -122.00  -2.00   1.00   30.00    --  -38.00 -77.00  60.00  120
 23  \w   -122.00 -94.00   1.00   30.00    --  -38.00 -77.00 -90.00   28
 24  \w   -116.00  -5.00   1.00   30.00    --  -38.00 -57.00 150.00  111
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0722395000
_diffrn_orient_matrix_UB_12      0.0378993000
_diffrn_orient_matrix_UB_13      0.0200054000
_diffrn_orient_matrix_UB_21      0.0807839000
_diffrn_orient_matrix_UB_22      -0.0449117000
_diffrn_orient_matrix_UB_23      -0.0570745000
_diffrn_orient_matrix_UB_31      -0.0439193000
_diffrn_orient_matrix_UB_32      0.0833596000
_diffrn_orient_matrix_UB_33      -0.0366650000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37622
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.511
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             1836
_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.736
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1113
_refine_ls_number_reflns         16684
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0868
_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^)+(0.1606P)^2^+4.8512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.3401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8214
_reflns_number_total             16684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02533j2.cif
_cod_data_source_block           kaj19_s1741_2
_cod_database_code               1558358
_sydney_internal_submission_code kaj19_s1741_2
_sydney_internal_submission_date 2019-02-15
_sydney_internal_submission_number s1741
_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 2019-02-25
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-03-06
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-03-11
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-03-11
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-03-11
_sydney_internal_check_user      wlew0588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C98H150N12O4S4
_chemical_oxdiff_usercomment     'SB-1-100 plus TBA(2) Adipate'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.855
_reflns_odcompleteness_completeness 98.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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
 N1-H1 = N2-H2 = N3-H3 = N4-H4 = N5-H5 = N6-H6 = N7-H7 = N8-H8 = N9-H9 = N10-H10
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C22(H22A,H22B), C37(H37A,H37B), C44(H44A,H44B), C62(H62A,
 H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C67(H67A,H67B),
 C68(H68A,H68B), C69(H69A,H69B), 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),
 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)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C7(H7A), C10(H10A), C12(H12), C17(H17), C18(H18), C20(H20), C21(H21),
  C27(H27), C29(H29), C32(H32), C34(H34), C39(H39), C40(H40), C42(H42), C43(H43)
3.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C50(H50A,H50B,
 H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C59(H59A,H59B,H59C),
 C60(H60A,H60B,H60C), C70(H70A,H70B,H70C), C74(H74A,H74B,H74C), C78(H78A,H78B,
 H78C), C82(H82A,H82B,H82C), C86(H86A,H86B,H86C), C90(H90A,H90B,H90C), C94(H94A,
 H94B,H94C), C98(H98A,H98B,H98C)
;
_shelx_res_checksum              69749
_olex2_date_sample_data_collection 2019-03-06
_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) Adipate'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   9928
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.301