New core-expanded calix[4]pyrroles and N-donor-extended dipyrromethanes: syntheses, anion binding and conformational studies.
Mishra, Soumya; Giri, Monalisa; Mishra, Vipin Kumar; Guchhait, Tapas; Organic & biomolecular chemistry 24 (2026) 708–719; doi:10.1039/d5ob01716e

data_7161033
_publ_section_title
;
 New core-expanded calix[4]pyrroles and N-donor-extended dipyrromethanes:
 syntheses, anion binding and conformational studies.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              708
_journal_page_last               719
_journal_paper_doi               10.1039/d5ob01716e
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '2(H2 O), C28 H38 N6'
_chemical_formula_sum            'C28 H42 N6 O2'
_chemical_formula_weight         494.67
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-20
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-20 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.087(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.4050(14)
_cell_length_b                   6.2059(3)
_cell_length_c                   20.1630(10)
_cell_measurement_reflns_used    11538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.798
_cell_measurement_theta_min      1.902
_cell_volume                     2679.8(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11538
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.798
_diffrn_reflns_theta_min         1.902
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1705 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4843
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0482P)^2^+0.8526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.773
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                4485
_reflns_number_total             4843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01716e2.cif
_cod_data_source_block           tg1
_cod_database_code               7161033
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.988
_diffrn_oxdiff_ac3_digest_hkl    41a01de8a420d28b4605a0b1e471cc2c569617
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C14(H14A,H14B), C28(H28A,H28B), C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N5(H5), N4(H4), N2(H2), C23(H23), C3(H3), C2(H2A), C24(H24), C17(H17),
  C10(H10), C16(H16), C9(H9)
1.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C),
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_olex2_submission_original_sample_id 'macrocycle 1'
_olex2_submission_special_instructions 'No special instructions were received'