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_7161035
_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         'C38 H40 N8 O4, H2 O'
_chemical_formula_sum            'C38 H42 N8 O5'
_chemical_formula_weight         690.79
_chemical_name_systematic        'Azacalix dipyrromethane'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-12-01
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-07 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.3406(9)
_cell_length_b                   10.6824(3)
_cell_length_c                   21.5560(6)
_cell_measurement_reflns_used    4270
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.197
_cell_measurement_theta_min      1.889
_cell_volume                     6986.5(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SHELXL 2018/3 (Sheldrick, 2018)'
_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, 2018)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22800
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.197
_diffrn_reflns_theta_max         24.197
_diffrn_reflns_theta_min         1.889
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             2928
_exptl_crystal_preparation       'Mannich reaction'
_exptl_crystal_recrystallization_method
'Diffusion of n-Hexane into DCM solution of compound'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0577P)^2^+1.8870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4270
_reflns_number_total             5503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01716e2.cif
_cod_data_source_block           sm8out
_cod_database_code               7161035
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C24(H24A,H24B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21), C22(H22), C28(H28), C29(H29), C34(H34), C35(H35), C37(H37), C38(H38)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              17330
_olex2_date_sample_completion    2024-11-07
_olex2_date_sample_data_collection 2024-11-07
_olex2_date_sample_submission    2024-11-07
_olex2_submission_original_sample_id 'SM 8'
_olex2_submission_special_instructions 'No special instructions were received'