Small cavitand macrocycles from direct C-C coupling of <i>s</i>-aryl tetrazine units.
Mboyi, Clève D; Sabbadin, Henri; Penouilh, Marie-José; Bonnin, Quentin; Amardeil, Régine; Cattey, Hélène; Fournier, Sophie; Devillers, Charles H.; Roger, Julien; Hierso, Jean-Cyrille; Chemical communications (Cambridge, England) 62 (2026) 6987–6991; doi:10.1039/d6cc00124f

data_7135593
_publ_section_title
;
 Small cavitand macrocycles from direct C-C coupling of <i>s</i>-aryl
 tetrazine units.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6987
_journal_page_last               6991
_journal_paper_doi               10.1039/d6cc00124f
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C42 H18 F6 N12, C4 H8 O'
_chemical_formula_sum            'C46 H26 F6 N12 O'
_chemical_formula_weight         876.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2025-11-07 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5165(8)
_cell_length_b                   12.9555(7)
_cell_length_c                   21.3838(11)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.040
_cell_measurement_theta_min      2.450
_cell_volume                     3945.0(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            74654
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.092
_diffrn_reflns_theta_min         2.218
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9333.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of diethylether and DCM  by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8675
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+3.7167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5333
_reflns_number_total             8675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00124f2.cif
_cod_data_source_block           Compound_6b
_cod_depositor_comments
'Adding full bibliography for 7135589--7135593.cif.'
_cod_database_code               7135593
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C45 \\sim O1B-C45B
 with sigma of 0.02
 O1-C44 \\sim O1B-C44B
 with sigma of 0.02
 C46-C45 \\sim C46B-C45B
 with sigma of 0.02
 O1-C46 \\sim O1B-C46B
 with sigma of 0.04
 C43-C44 \\sim C43B-C44B
 with sigma of 0.02
 O1-C43 \\sim O1B-C43B
 with sigma of 0.04
 C45-C44 \\sim C45B-C44B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C44B \\sim C43B \\sim O1B \\sim C45B \\sim C46B \\sim C44 \\sim O1 \\sim C45
\\sim C46 \\sim C43: within 1.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008 within 1.7A
4. Others
 Fixed Sof: O1(0.75) C46(0.75) H46A(0.75) H46B(0.75) H46C(0.75) C45(0.75)
 H45(0.75) C43(0.75) H43A(0.75) H43B(0.75) H43C(0.75) C44(0.75) H44(0.75)
 C43B(0.25) H43D(0.25) H43E(0.25) H43F(0.25) C44B(0.25) H44B(0.25) O1B(0.25)
 C45B(0.25) H45B(0.25) C46B(0.25) H46D(0.25) H46E(0.25) H46F(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C20(H20), C24(H24), C19(H19), C25(H25), C18(H18), C34(H34),
 C37(H37), C33(H33), C32(H32), C6(H6), C39(H39), C4(H4), C9(H9), C38(H38),
 C5(H5), C11(H11), C10(H10), C45(H45), C44(H44), C44B(H44B), C45B(H45B)
5.b Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C43(H43A,H43B,H43C), C43B(H43D,H43E,H43F), C46B(H46D,
 H46E,H46F)
;
_shelx_res_checksum              81836
_shelx_hkl_checksum              37910
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'