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_1574563
_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, 1.75(C H4 O), H O0.75, 1.65(H2 O)'
_chemical_formula_sum            'C49.75 H61.3 Cl3 K N4 O18.15'
_chemical_formula_weight         1151.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-03 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.685(2)
_cell_angle_beta                 105.563(2)
_cell_angle_gamma                108.209(3)
_cell_formula_units_Z            2
_cell_length_a                   12.0536(4)
_cell_length_b                   14.4733(5)
_cell_length_c                   17.4640(5)
_cell_measurement_reflns_used    10178
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.9920
_cell_measurement_theta_min      2.0000
_cell_volume                     2772.69(17)
_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 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      113.15
_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    -36.00  66.00   0.50  126.02    --  -13.19  46.00-100.00  204
  2  \w     65.00  95.00   0.50  126.02    --   12.56 178.00  60.00   60
  3  \w     46.00  93.00   0.50  126.02    --   12.56 178.00 120.00   94
  4  \w     49.00  92.00   0.50  126.02    --   12.56 178.00  30.00   86
  5  \w     46.00  74.00   0.50  126.02    --   12.56 178.00 -60.00   56
  6  \w     46.00  81.00   0.50  126.02    --   12.56 178.00 150.00   70
  7  \w    -68.00 -25.00   0.50  126.02    --   12.56 -19.00  90.00   86
  8  \w    -21.00  32.00   0.50  126.02    --  -13.19 -99.00  90.00  106
  9  \w    -66.00 -41.00   0.50  126.02    --  -13.19-178.00 -30.00   50
 10  \w    -97.00 -41.00   0.50  126.02    --  -13.19-178.00   0.00  112
 11  \w    -86.00  10.00   0.50  126.02    --  -13.19 -46.00 109.00  192
;
_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      0.0361722000
_diffrn_orient_matrix_UB_12      0.0248224000
_diffrn_orient_matrix_UB_13      -0.0242373000
_diffrn_orient_matrix_UB_21      0.0217203000
_diffrn_orient_matrix_UB_22      -0.0399781000
_diffrn_orient_matrix_UB_23      -0.0018380000
_diffrn_orient_matrix_UB_31      -0.0489919000
_diffrn_orient_matrix_UB_32      -0.0218338000
_diffrn_orient_matrix_UB_33      -0.0347332000
_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  0.0492
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34566
_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         1.822
_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  0.707
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             1206
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.018
_refine_diff_density_max         1.379
_refine_diff_density_min         -1.283
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         11304
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          2.999
_refine_ls_shift/su_mean         0.104
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1062P)^2^+3.4644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8310
_reflns_number_total             11304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00252d2.cif
_cod_data_source_block           20241214_b15cr5-nh-aac-ph_k_1
_cod_depositor_comments
'Adding full bibliography for 1574562--1574564.cif.'
_cod_original_cell_volume        2772.69(16)
_cod_original_formula_sum        'C49.75 H61.30 Cl3 K N4 O18.15'
_cod_database_code               1574563
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C48 H50 Cl3 K1 N4 O14'
_reflns_odcompleteness_completeness 99.94
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O2-H2A \\sim O2A-H2AA
 with sigma of 0.02
 O2-H2B \\sim O2A-H2AB
 with sigma of 0.02
 H2A-H2B \\sim H2AA-H2AB
 with sigma of 0.04
3. Others
 Fixed Sof: O01Y(0.75) H6(0.25) HD(0.75) O01Z(0.75) H5(0.75) O021(0.75)
 H02K(0.75) H02L(0.75) C025(0.75) H02H(0.75) H02I(0.75) H02J(0.75) O2(0.2)
 H2A(0.2) H2B(0.2) O1(0.5) H1A(0.5) H1B(0.5) O2A(0.2) H2AA(0.2) H2AB(0.2)
4.a Free rotating group:
 O01Y(H6,HD), O021(H02K,H02L), O2(H2A,H2B), O1(H1A,H1B), O2A(H2AA,H2AB)
4.b Secondary CH2 refined with riding coordinates:
 C00W(H00A,H00B), C010(H01A,H01B), C01C(H01C,H01D), C01D(H01E,H01F), C01G(H01I,
 H01J), C01H(H01K,H01L), C01M(H01P,H01Q), C01N(H01R,H01S), C01P(H01U,H01V),
 C01Q(H01W,H01X), C01R(H01Y,H), C01S(H01Z,HA), C01T(H01,HB), C01X(H4,HC),
 C020(H02A,H02B), C023(H02C,H02D)
4.c Aromatic/amide H refined with riding coordinates:
 N00K(H00K), N00L(H00L), C00V(H00V), C00X(H00X), C00Z(H00Z), C011(H011),
 C016(H016), C017(H017), C019(H019), C01E(H01G), C01F(H01H), C01J(H01M),
 C01K(H01N), C01L(H01O), C01O(H01T), C01U(H1), C01V(H2), C01W(H3)
4.d Idealised Me refined as rotating group:
 C022(H02E,H02F,H02G), C025(H02H,H02I,H02J)
4.e Idealised tetrahedral OH refined as rotating group:
 O00N(H00N), O01Z(H5)
;
_shelx_res_checksum              10537
_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 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.760