Cubane-1,3-dicarboxamides as structural isosteres for isophthalamides in hydrogen bond templated interlocked molecules.
Barlow, Sean R.; Halcovitch, Nathan R.; Akien, Geoffrey R.; Coote, Susannah C.; Evans, Nicholas H.; Chemical communications (Cambridge, England) 60 (2024) 11532–11535; doi:10.1039/d4cc01859a

data_7133721
_publ_section_title
;
 Cubane-1,3-dicarboxamides as structural isosteres for isophthalamides in
 hydrogen bond templated interlocked molecules.
;
_journal_issue                   81
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11532
_journal_page_last               11535
_journal_paper_doi               10.1039/d4cc01859a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H32 N2 O5, 2(H2 O)'
_chemical_formula_sum            'C30 H36 N2 O7'
_chemical_formula_weight         536.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-09-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.237(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   52.946(3)
_cell_length_b                   10.4697(6)
_cell_length_c                   9.7763(5)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.5890
_cell_measurement_theta_min      4.2480
_cell_volume                     5396.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -57.00  33.00   1.00    7.50    --  -41.18  37.00  30.00   90
  2  \w   -114.00 -19.00   1.00    7.50    --  -41.18 -57.00-120.00   95
  3  \w    -87.00 -60.00   1.00    7.50    --  -41.18-152.00  -1.00   27
  4  \w     35.00 109.00   1.00   30.00    --  107.34-111.00-120.00   74
  5  \w     45.00 131.00   1.00   30.00    --  107.34 -45.00-180.00   86
  6  \w     34.00 124.00   1.00   30.00    --  107.34 -45.00   0.00   90
  7  \w    135.00 178.00   1.00   30.00    --  107.34 111.00 -60.00   43
  8  \w     81.00 178.00   1.00   30.00    --  107.34  61.00 150.00   97
  9  \w   -114.00 -13.00   1.00    7.50    --  -41.18 -57.00  30.00  101
 10  \w    -87.00  -6.00   1.00    7.50    --  -41.18 125.00 150.00   81
 11  \w     55.00 178.00   1.00   30.00    --  107.34  15.00   0.00  123
 12  \w     79.00 178.00   1.00   30.00    --  107.34  30.00-120.00   99
 13  \w     34.00 109.00   1.00   30.00    --  107.34-111.00   0.00   75
 14  \w     79.00 178.00   1.00   30.00    --  107.34  30.00  90.00   99
 15  \w   -114.00 -44.00   1.00    7.50    --  -41.18 -57.00 -60.00   70
 16  \w   -114.00 -13.00   1.00    7.50    --  -41.18 -57.00 120.00  101
 17  \w     54.00 109.00   1.00   30.00    --  107.34-111.00  60.00   55
 18  \w     36.00  63.00   1.00   30.00    --  107.34-111.00 -60.00   27
 19  \w     68.00 108.00   1.00   30.00    --  107.34-111.00 -60.00   40
 20  \w     56.00 135.00   1.00   30.00    --  107.34 -77.00  90.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       65
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9678
_diffrn_reflns_point_group_measured_fraction_full 0.615
_diffrn_reflns_point_group_measured_fraction_max 0.602
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.893
_diffrn_reflns_theta_min         4.305
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.529
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         9678
_refine_ls_number_restraints     918
_refine_ls_restrained_S_all      1.565
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.1099
_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          0.3276
_refine_ls_wR_factor_ref         0.3505
_reflns_Friedel_coverage         0.228
_reflns_Friedel_fraction_full    0.230
_reflns_Friedel_fraction_max     0.224
_reflns_number_gt                7922
_reflns_number_total             9678
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9724\% 
around [1.00 -0.00 -0.00] (reciprocal) or [0.90 -0.01 0.44] (direct)
;
_cod_data_source_file            d4cc01859a2.cif
_cod_data_source_block           ne155_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7133721--7133722.cif.'
_cod_database_code               7133721
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.591(4)
 0.409(4)
2. 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 O(H,H) groups
3. Restrained distances
 O9-H9B = O9-H9A = O8-H8B = O8-H8C = O7-H7C = O7-H7B = O6-H6B = O6-H6C
 1 with sigma of 0.02
 H6C-O2
 2.1 with sigma of 0.005
 H8B-O9
 2.1 with sigma of 0.005
 H7B-H6B
 2.6 with sigma of 0.02
 O7-O6 \\sim O6-O2
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C11A)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C4) \\sim Ueq,
Uanis(C7A) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1A) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C9A)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C29A) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C2A) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C8A)
\\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C14A) \\sim Ueq,
Uanis(C16A) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C24A) \\sim Ueq, Uanis(C27) \\sim Ueq,
Uanis(C26A) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(O3A) \\sim Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.01
Uanis(N2) \\sim Ueq, Uanis(C2A) \\sim Ueq: with sigma of 0.008 and sigma for
terminal atoms of 0.016
Uanis(C8A) = Uanis(C2A)
5. Rigid body (RIGU) restrains
 O2, O1, C9, N1, C1, C10, C2, C4, C5, C11, C3, C6, C8, C12, C16, C7, C30, C13,
 C15, O5, N2, C14, C29, C17, C26, C25, C27, C18, C24, C28, C19, C23, O3, C22,
 C20, O4, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20A, O1A, C9A, C1A, N1A, C2A, C4A, C5A, C10A, C3A, C6A, C8A, C11A, C7A, C30A,
  C12A, C16A, N2A, O5A, C13A, C15A, C29A, C14A, C26A, C17A, C25A, C27A, O2A,
 C24A, C28A, C18A, C23A, C19A, C22A, O3A, O4A, C21A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed X: O7(0.489709)
 Fixed Y: O7(0.540629)
 Fixed Z: O7(0.69052)
7.a Free rotating group:
 O6(H6B,H6C), O7(H7B,H7C), O8(H8B,H8C), O9(H9A,H9B)
7.b Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C2A(H2AB), C4A(H4A),
 C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A)
7.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C29(H29A,H29B), C10A(H10C,H10D),
 C17A(H17C,H17D), C18A(H18C,H18D), C19A(H19C,H19D), C20A(H20C,H20D), C21A(H21C,
 H21D), C22A(H22C,H22D), C29A(H29C,H29D)
7.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C12(H12), C13(H13), C15(H15), C16(H16), C24(H24), C25(H25),
 C27(H27), C28(H28), N1A(H1A), N2A(H2AA), C12A(H12A), C13A(H13A), C15A(H15A),
 C16A(H16A), C24A(H24A), C25A(H25A), C27A(H27A), C28A(H28A)
7.e Fitted hexagon refined as free rotating group:
 C11A(C12A,C13A,C14A,C15A,C16A)
;
_shelx_res_checksum              90348
_shelx_hkl_checksum              1723
_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
;