Crystal structures of sandwich-type potassium cation complexes formed from benzo-15-crown-5-based ligand containing a chloromaleimide moiety
Hirayama, Yuto; Ito, Akitaka; Ochi, Rika; CrystEngComm 27 (2025) 3214–3218; doi:10.1039/D5CE00252D

data_1574564
_publ_section_title
;
 Crystal structures of sandwich-type potassium cation complexes formed
 from benzo-15-crown-5-based ligand containing a chloromaleimide moiety
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3214
_journal_page_last               3218
_journal_paper_doi               10.1039/D5CE00252D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C48 H50 Cl2 K N4 O14, Cl, 6[H2O]'
_chemical_formula_sum            'C48 H56 Cl3 K N4 O19.6'
_chemical_formula_weight         1148.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-03-03 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.663(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1444(4)
_cell_length_b                   23.9026(5)
_cell_length_c                   15.8158(6)
_cell_measurement_reflns_used    13211
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      30.0510
_cell_measurement_theta_min      2.1380
_cell_volume                     5563.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -39.00 -13.00   0.50   67.26    --  -13.19 -57.00   0.00   52
  2  \w    -77.00  -1.00   0.50   67.26    --  -13.19 -47.00  19.00  152
  3  \w    -36.00  48.00   0.50   67.26    --  -13.19  47.00 168.00  168
  4  \w    -86.00 -55.00   0.50   67.26    --  -13.19 -57.00   0.00   62
  5  \w     42.00  83.00   0.50   67.26    --   12.56 178.00   0.00   82
  6  \w     44.00  89.00   0.50   67.26    --   12.56 178.00  30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0359027000
_diffrn_orient_matrix_UB_12      0.0012196000
_diffrn_orient_matrix_UB_13      -0.0379827000
_diffrn_orient_matrix_UB_21      -0.0269865000
_diffrn_orient_matrix_UB_22      -0.0173036000
_diffrn_orient_matrix_UB_23      0.0203022000
_diffrn_orient_matrix_UB_31      -0.0176157000
_diffrn_orient_matrix_UB_32      0.0240949000
_diffrn_orient_matrix_UB_33      0.0164236000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0506
_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       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38344
_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         26.372
_diffrn_reflns_theta_min         1.879
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             2395
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.032
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     758
_refine_ls_number_reflns         11373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0685P)^2^+6.3522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8060
_reflns_number_total             11373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00252d2.cif
_cod_data_source_block           20240621_15-cr-5-aac-phe_1
_cod_depositor_comments
'Adding full bibliography for 1574562--1574564.cif.'
_cod_original_formula_sum        'C48 H56 Cl3 K N4 O19.60'
_cod_database_code               1574564
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H24 Cl2 N1 O7  K1'
_diffrn_oxdiff_digest_frames
;
01a36653650ce36cce81b6e4bcb8204d5a00606509f
;
_diffrn_oxdiff_digest_hkl
;
018cb3fd66a1bf5cb4da6769dd33c4ad0dbf00
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O00F(0.75) O00I(0.75) O00N(0.75) H2(0.75) HA(0.75) HB(0.25)
 HC(0.25) H4(0.75) HD(0.75) HE(0.25) HF(0.25) C01Z(0.75) H5(0.75) HG(0.75)
 C020(0.75) H02A(0.75) H02B(0.75) C021(0.75) H02C(0.75) H02D(0.75) C022(0.75)
 H02E(0.75) H02F(0.75) O4(0.8) O5(0.5) O6(0.5) O7(0.2) O8(0.2) O9(0.2) O10(0.2)
 C2(0.25) H2A(0.25) H2B(0.25) O12(0.25) C4(0.25) H4A(0.25) H4B(0.25) O11(0.25)
 C10(0.25) H10A(0.25) H10B(0.25) C11(0.25) H11A(0.25) H11B(0.25) O17(0.25)
3.a Free rotating group:
 O1(H1A,H1B), O3(H3A,H3B), O2(H2C,H2D)
3.b Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C01C(H01C,H01D), C01E(H01F,H01G), C01F(H01H,H01I), C01G(H01J,
 H01K), C01H(H01L,H01M), C01J(H01O,H01P), C01K(H01Q,H01R), C01L(H01S,H01T),
 C01S(H01,H), C01V(H2,HA), C01V(HB,HC), C01Y(H4,HD), C01Y(HE,HF), C01Z(H5,HG),
 C020(H02A,H02B), C021(H02C,H02D), C022(H02E,H02F), C2(H2A,H2B), C4(H4A,H4B),
 C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N00J(H00J), N00M(H00M), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C016(H016), C018(H018), C01D(H01E), C01I(H01N), C01M(H01U), C01N(H01V),
 C01O(H01W), C01P(H01X), C01Q(H01Y), C01R(H01Z), C01U(H1), C01W(H3)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.752