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_7133722
_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_formula_moiety         'C36 H32 N4 O4, C32 H30 N2 O2, [+ solvents]'
_chemical_formula_sum            'C71 H65 Cl9 N6 O6'
_chemical_formula_weight         1417.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1773(3)
_cell_length_b                   20.9754(3)
_cell_length_c                   15.2190(2)
_cell_measurement_reflns_used    14115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2180
_cell_measurement_theta_min      3.9760
_cell_volume                     7079.54(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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 2014/4 (Sheldrick, 2014)'
_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 0.977
_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    -73.00 -47.00   1.00    3.00    --  -41.48 125.00 -30.00   26
  2  \w   -102.00 -13.00   1.00    3.00    --  -41.48 -57.00 120.00   89
  3  \w   -116.00 -59.00   1.00    3.00    --  -41.48 -37.00-120.00   57
  4  \w     61.00  87.00   1.00    3.00    --   41.48-125.00-170.00   26
  5  \w    105.00 148.00   1.00   16.00    --  112.00  77.00 -90.00   43
  6  \w     88.00 166.00   1.00   16.00    --  112.00  45.00  60.00   78
  7  \w     66.00 104.00   1.00   16.00    --  112.00-111.00-150.00   38
  8  \w     64.00 143.00   1.00   16.00    --  112.00 178.00-120.00   79
  9  \w     40.00 101.00   1.00   16.00    --  112.00 -61.00 -30.00   61
 10  \w     14.00  39.00   1.00    3.00    --  -41.48  19.00 150.00   25
 11  \w   -114.00 -13.00   1.00    3.00    --  -41.48 -57.00   0.00  101
 12  \w   -114.00 -13.00   1.00    3.00    --  -41.48 -57.00-120.00  101
 13  \w    -87.00  -6.00   1.00    3.00    --  -41.48 125.00 150.00   81
 14  \w    -87.00 -62.00   1.00    3.00    --  -41.48 125.00 -92.00   25
;
_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_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.261
_diffrn_reflns_theta_min         3.987
_exptl_absorpt_coefficient_mu    3.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (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    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             2936
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7251
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1418P)^2^+7.6773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2500
_refine_ls_wR_factor_ref         0.2599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6167
_reflns_number_total             7251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01859a2.cif
_cod_data_source_block           ne145_auto
_cod_depositor_comments
'Adding full bibliography for 7133721--7133722.cif.'
_cod_database_code               7133722
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.665
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N3-H3
 1 with sigma of 0.02
 N2-H2
 1 with sigma of 0.02
 C32-C33 \\sim C38-C39
 with sigma of 0.02
 C32-C31 \\sim C38-C37
 with sigma of 0.02
 C33-C31 \\sim C39-C37
 with sigma of 0.04
 C36-C35 \\sim C30-C29 \\sim C31-C30 \\sim C37-C36 \\sim C32-C31 \\sim C38-C37
\\sim C33-C32 \\sim C34-C33
 \\sim C39-C38 \\sim C40-C39 \\sim C34-C29 \\sim C40-C35
 with sigma of 0.002
 C29-C22 \\sim C35-C22
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C36) = Uanis(C30)
Uanis(C40) = Uanis(C34)
Uanis(C35) = Uanis(C29)
Uanis(C39) = Uanis(C33)
Uanis(C37) = Uanis(C31)
Uanis(C38) = Uanis(C32)
4. Others
 Sof(H22A)=Sof(C35)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=
 Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=1-FVAR(1)
 Sof(H22)=Sof(C29)=Sof(C32)=Sof(H32)=Sof(C30)=Sof(H30)=Sof(C34)=Sof(H34)=
 Sof(C33)=Sof(H33)=Sof(C31)=Sof(H31)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C18(H18), C4(H4), C43(H43), C2(H2A), C3(H3A), C6(H6), C22(H22), C22(H22A)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C15(H15A,H15B), C8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C13(H13), C11(H11), C10(H10), C14(H14), C24(H24), C25(H25),
 C28(H28), C26(H26), C27(H27), C32(H32), C30(H30), C34(H34), C33(H33), C31(H31),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 662 electrons were 
found in a volume of 1994 A^3 in 2 voids per unit cell. 
This is consistent with the presence of 
2[CHCl3], 1[CHCl3] per Asymmetric Unit 
which account for 696 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              40932
_shelx_hkl_checksum              97792
_shelx_fab_checksum              5913
_olex2_exptl_crystal_mounting_method
'mounted on a Mitegen loop using Paratone-N oil'
_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
;