Interplay between molecular recognition and acid-base reactivity in tailored metal-based calix[6]arene receptors.
Lepeintre, Martin; Višnjevac, Aleksandar; Jabin, Ivan; Colasson, Benoit; Organic & biomolecular chemistry 23 (2025) 8012–8022; doi:10.1039/d5ob01099c

data_7160660
_publ_section_title
;
 Interplay between molecular recognition and acid-base reactivity in
 tailored metal-based calix[6]arene receptors.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8012
_journal_page_last               8022
_journal_paper_doi               10.1039/d5ob01099c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C59 H57 N7 O6 Zn, 2(C2 H3 N), 2(Cl O4)'
_chemical_formula_sum            'C63 H63 Cl2 N9 O14 Zn'
_chemical_formula_weight         1306.555
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2024-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.7263(6)
_cell_angle_beta                 81.2491(7)
_cell_angle_gamma                86.7523(6)
_cell_formula_units_Z            2
_cell_length_a                   13.22765(11)
_cell_length_b                   14.15549(10)
_cell_length_c                   17.82870(14)
_cell_measurement_reflns_used    31988
_cell_measurement_temperature    120
_cell_measurement_theta_max      79.4870
_cell_measurement_theta_min      3.3740
_cell_volume                     3286.80(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9798
_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     -4.00  22.00   0.50    0.24    --  -48.38  96.00  11.00   52
  2  \w    -73.00 -16.00   0.50    0.24    --  -48.38  96.00  11.00  114
  3  \w     -7.00  62.00   0.50    0.24    --   48.38 -96.00 -97.00  138
  4  \w    -66.00 -40.00   0.50    0.95    --  -90.00  96.00  11.00   52
  5  \w    108.00 143.00   0.50    0.95    --  111.50  96.00  11.00   70
  6  \w     41.00 103.00   0.50    0.95    --  111.50 -96.00 -97.00  124
  7  \w   -119.00 -39.00   0.50    0.24    --  -48.38 -77.00 -90.00  160
  8  \w    -29.00  24.00   0.50    0.24    --  -48.38  38.00 150.00  106
  9  \w   -120.00 -37.00   0.50    0.24    --  -48.38 -38.00  30.00  166
 10  \w     -4.00  22.00   0.50    0.24    --   48.38 -19.00   0.00   52
 11  \w     37.00  80.00   0.50    0.24    --   48.38 -99.00-150.00   86
 12  \w    -24.00  11.00   0.50    0.24    --   48.38 -19.00 -90.00   70
 13  \w    -22.00  43.00   0.50    0.24    --   48.38 -38.00 -60.00  130
 14  \w    -51.00 -26.00   0.50    0.95    --  -90.00  45.00 -30.00   50
 15  \w   -161.00-107.00   0.50    0.95    --  -90.00 -95.00   0.00  108
 16  \w    -46.00 -18.00   0.50    0.95    --  -90.00  45.00  30.00   56
 17  \w   -146.00-121.00   0.50    0.95    --  -90.00 -96.00 -97.00   50
 18  \w     49.00 110.00   0.50    0.95    --  111.50-125.00-120.00  122
 19  \w     40.00  65.00   0.50    0.95    --  111.50 -61.00 120.00   50
 20  \w     45.00  87.00   0.50    0.95    --  111.50 -95.00 120.00   84
 21  \w     54.00 105.00   0.50    0.95    --  111.50 -77.00 -90.00  102
 22  \w     41.00  84.00   0.50    0.95    --  111.50 -77.00 150.00   86
 23  \w     44.00 107.00   0.50    0.95    --  111.50-105.00 111.95  126
 24  \w     41.00  71.00   0.50    0.95    --  111.50 -61.00 150.00   60
 25  \w     40.00  84.00   0.50    0.95    --  111.50 -95.00 -30.00   88
 26  \w     51.00  96.00   0.50    0.95    --  111.50 -95.00   0.00   90
 27  \w     85.00 111.00   0.50    0.95    --  111.50-125.00 -90.00   52
 28  \w     40.00  69.00   0.50    0.95    --  111.50 -95.00  60.00   58
 29  \w     75.00 111.00   0.50    0.95    --  111.50-125.00-180.00   72
 30  \w     44.00  69.00   0.50    0.95    --  111.50 -61.00 -90.00   50
 31  \w    107.00 178.00   0.50    0.95    --  111.50  45.00-180.00  142
 32  \w     40.00 101.00   0.50    0.95    --  111.50 -95.00  30.00  122
 33  \w    105.00 178.00   0.50    0.95    --  111.50  45.00-120.00  146
 34  \w     80.00 105.00   0.50    0.95    --  111.50 -95.00  90.00   50
 35  \w     46.00  71.00   0.50    0.95    --  111.50-143.00  55.58   50
 36  \w     91.00 125.00   0.50    0.95    --  111.50-143.00  55.58   68
 37  \w     42.00  68.00   0.50    0.95    --  111.50-125.00 -90.00   52
 38  \w    129.00 169.00   0.50    0.95    --  111.50   0.00-180.00   80
 39  \w    102.00 177.00   0.50    0.95    --  111.50  15.00 -60.00  150
 40  \w    104.00 157.00   0.50    0.95    --  111.50  30.00 150.00  106
 41  \w    103.00 177.00   0.50    0.95    --  111.50 125.00-180.00  148
 42  \w     44.00 116.00   0.50    0.95    --  111.50   0.00-180.00  144
 43  \w     62.00 118.00   0.50    0.95    --  111.50-133.00 -12.99  112
 44  \w     41.00  73.00   0.50    0.95    --  111.50 -95.00  90.00   64
 45  \w     83.00 109.00   0.50    0.95    --  111.50-125.00-150.00   52
 46  \w    114.00 139.00   0.50    0.95    --  111.50 125.00 -30.00   50
 47  \w    146.00 172.00   0.50    0.95    --  111.50 125.00 -30.00   52
 48  \w    106.00 172.00   0.50    0.95    --  111.50  30.00   0.00  132
 49  \w     42.00 100.00   0.50    0.95    --  111.50 -95.00-120.00  116
 50  \w    125.00 154.00   0.50    0.95    --  111.50  45.00  30.00   58
 51  \w     43.00  69.00   0.50    0.95    --  111.50 -61.00-120.00   52
 52  \w     46.00  71.00   0.50    0.95    --  111.50 -61.00 -60.00   50
 53  \w    141.00 168.00   0.50    0.95    --  111.50  15.00 -30.00   54
 54  \w    101.00 136.00   0.50    0.95    --  111.50  15.00 -30.00   70
 55  \w     86.00 111.00   0.50    0.95    --  111.50-125.00  90.00   50
 56  \w     46.00  71.00   0.50    0.95    --  111.50 -61.00   0.00   50
 57  \w    102.00 127.00   0.50    0.95    --  111.50-147.00  18.58   50
 58  \w     54.00 100.00   0.50    0.95    --  111.50 -95.00 150.00   92
 59  \w     44.00  70.00   0.50    0.95    --  111.50-125.00  60.00   52
 60  \w     86.00 111.00   0.50    0.95    --  111.50-125.00 120.00   50
 61  \w     42.00  67.00   0.50    0.95    --  111.50-125.00 150.00   50
 62  \w     40.00  66.00   0.50    0.95    --  111.50 -61.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0621434000
_diffrn_orient_matrix_UB_12      -0.0624124000
_diffrn_orient_matrix_UB_13      -0.0594920000
_diffrn_orient_matrix_UB_21      0.0743595000
_diffrn_orient_matrix_UB_22      -0.0316836000
_diffrn_orient_matrix_UB_23      0.0566459000
_diffrn_orient_matrix_UB_31      -0.0672596000
_diffrn_orient_matrix_UB_32      -0.0838838000
_diffrn_orient_matrix_UB_33      0.0304900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9798
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            57834
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9798
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.85
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       prism
_exptl_crystal_F_000             1362.909
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.7911
_refine_diff_density_min         -1.4878
_refine_diff_density_rms         0.0697
_refine_ls_d_res_high            0.7832
_refine_ls_d_res_low             14.1012
_refine_ls_extinction_coef       0.00026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    105
_refine_ls_number_parameters     812
_refine_ls_number_reflns         14021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0269
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+3.9958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                12432
_reflns_number_total             14021
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01099c2.cif
_cod_data_source_block           exp_234_auto
_cod_depositor_comments
'Adding full bibliography for 7160658--7160660.cif.'
_cod_original_formula_sum        'C63 H63 Cl2 N9 O14 Zn1'
_cod_database_code               7160660
_chemical_oxdiff_formula         C54H51N6O6Zn
_cell_oxdiff_angle_alpha         85.7263(6)
_cell_oxdiff_angle_beta          81.2491(7)
_cell_oxdiff_angle_gamma         86.7523(6)
_cell_oxdiff_length_a            13.22765(11)
_cell_oxdiff_length_b            14.15549(10)
_cell_oxdiff_length_c            17.82870(14)
_cell_oxdiff_measurement_reflns_used 31988
_cell_oxdiff_volume              3286.80(4)
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H96a,H96b,H96c} of C96, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H58a,H58b,H58c} of C58, {H46a,H46b,H46c} of C46, {H95a,
  H95b,H95c} of C95, {H77a,H77b,H77c} of C77, {H85a,H85b,H85c} of C85
2. Others
 Fixed U22: O100(19.599494)
 Fixed Uiso: H10a(1) H10b(1)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C15(H15a,H15b), C19(H19a,H19b), C25(H25a,H25b), C29(H29a,
 H29b), C33(H33a,H33b), C40(H40a,H40b), C52(H52a,H52b), C71(H71a,H71b)
3.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C36(H36), C37(H37), C38(H38), C43(H43),
 C44(H44), C48(H48), C49(H49), C50(H50), C55(H55), C56(H56), C59(H59), C60(H60),
  C61(H61), C63(H63), C64(H64), C65(H65), C67(H67), C68(H68), C69(H69),
 C74(H74), C75(H75)
3.c Idealised Me refined as rotating group:
 C46(H46a,H46b,H46c), C58(H58a,H58b,H58c), C77(H77a,H77b,H77c), C85(H85a,H85b,
 H85c), C95(H95a,H95b,H95c), C96(H96a,H96b,H96c)
3.d Idealised tetrahedral OH refined as rotating group:
 O62(H62), O66(H66), O78(H78)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.669