Polymorphs and stoichiometric variants of crown ether-based molecular complexes: exploring the landscape of conformational flexibility and supramolecular interactions
Winson, Cinu; Kandasamy, Saravanan; Divya, Indira S.; Wozniak, Krzysztof; Varughese, Sunil; CrystEngComm 27 (2025) 2698–2710; doi:10.1039/D5CE00025D

data_7250153
_publ_section_title
;
 Polymorphs and stoichiometric variants of crown ether-based molecular
 complexes: exploring the landscape of conformational flexibility and
 supramolecular interactions
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2698
_journal_page_last               2710
_journal_paper_doi               10.1039/D5CE00025D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H5 N3 O4), C20 H36 O6'
_chemical_formula_sum            'C38 H46 F4 I2 N6 O14'
_chemical_formula_weight         1140.623
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2024-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-12-23 deposited with the CCDC.	2025-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                68.084(3)
_cell_angle_beta                 66.508(3)
_cell_angle_gamma                64.091(3)
_cell_formula_units_Z            1
_cell_length_a                   10.5860(3)
_cell_length_b                   11.3120(4)
_cell_length_c                   11.3900(4)
_cell_measurement_reflns_used    10319
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8540
_cell_measurement_theta_min      4.3650
_cell_volume                     1091.91(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9815
_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    -33.00  29.00   0.50    0.05    --    0.00  60.00 -41.00  124
  2  \w    -95.00 -53.00   0.50    0.05    --    0.00-178.00-180.00   84
  3  \w     32.00  70.00   0.50    0.05    --    0.00  60.00 -41.00   76
  4  \w    -70.00 -20.00   0.50    0.05    --    0.00 -77.00 150.00  100
  5  \w    -34.00  34.00   0.50    0.05    --    0.00 -60.00 179.00  136
  6  \w    -69.00 -41.00   0.50    0.05    --    0.00 -60.00 179.00   56
  7  \w    -93.00 -41.00   0.50    0.05    --    0.00-178.00  30.00  104
  8  \w    -44.00  -7.00   0.50    0.05    --   14.00 109.00 -79.49   74
  9  \w    -37.00 -11.00   0.50    0.05    --   22.00 112.00 -40.29   52
 10  \w    -22.00   3.00   0.50    0.05    --   34.00 104.00 -21.36   50
 11  \w      7.00  41.00   0.50    0.05    --   38.00  85.00-132.36   68
 12  \w      2.00  27.00   0.50    0.05    --   54.00  96.00 -11.15   50
 13  \w     14.00  43.00   0.50    0.05    --   54.00  85.00  96.09   58
 14  \w      8.00  33.00   0.50    0.05    --   58.00  93.00  71.21   50
 15  \w     14.00  40.00   0.50    0.05    --   62.00  89.00 -88.93   52
 16  \w     16.00  41.00   0.50    0.05    --   66.00  92.00 137.32   50
 17  \w     16.00  41.00   0.50    0.05    --   66.00  92.00-179.44   50
 18  \w     17.00  42.00   0.50    0.05    --   66.00  90.00  74.41   50
 19  \w     16.00  41.00   0.50    0.05    --   66.00  92.00-128.77   50
 20  \w     32.00  98.00   0.50    0.05    --   66.60  60.00 -41.00  132
 21  \w    106.00 144.00   0.50    0.05    --   66.60  60.00 -41.00   76
 22  \w      5.00 102.00   0.50    0.05    --   66.60 -60.00 179.00  194
 23  \w    -21.00 135.00   0.50    0.05    --   66.60 -30.00-180.00  312
 24  \w     60.00 101.00   0.50    0.05    --   66.60 -94.00 -90.00   82
 25  \w     56.00  81.00   0.50    0.05    --   66.60 -94.00 -30.00   50
 26  \w     52.00 104.00   0.50    0.05    --   66.60 -94.00  60.00  104
 27  \w     24.00 109.00   0.50    0.05    --   66.60  77.00 -30.00  170
 28  \w    -17.00 108.00   0.50    0.05    --   66.60 -45.00 -60.00  250
 29  \w     62.00 108.00   0.50    0.05    --   66.60 -77.00   0.00   92
 30  \w     32.00  57.00   0.50    0.05    --   66.60 -77.00   0.00   50
 31  \w     33.00  66.00   0.50    0.05    --   74.00  76.00 -93.60   66
 32  \w     36.00  62.00   0.50    0.05    --   78.00  76.00  31.52   52
 33  \w     81.00 108.00   0.50    0.05    --   78.00  77.00-149.11   54
 34  \w     38.00  64.00   0.50    0.05    --   78.00  74.00  -4.75   52
 35  \w     37.00  72.00   0.50    0.05    --   78.00  77.00-149.11   70
 36  \w     40.00  66.00   0.50    0.05    --   82.00  76.00 153.84   52
 37  \w     43.00 109.00   0.50    0.05    --   82.00  77.00-179.96  132
 38  \w     40.00  66.00   0.50    0.05    --   82.00  77.00 -52.93   52
 39  \w     41.00  83.00   0.50    0.05    --   82.00  77.00  75.88   84
 40  \w     40.00  65.00   0.50    0.05    --   82.00  74.00 -85.68   50
 41  \w     44.00  70.00   0.50    0.05    --   86.00  75.00  -4.99   52
 42  \w     99.00 169.00   0.50    0.05    --   86.00  73.00-132.56  140
 43  \w     45.00  87.00   0.50    0.05    --   86.00  73.00-132.56   84
 44  \w     43.00  68.00   0.50    0.05    --   86.00  77.00 126.13   50
 45  \w     43.00  73.00   0.50    0.05    --   86.00  77.00  98.16   60
 46  \w     47.00  72.00   0.50    0.05    --   90.00  77.00  46.83   50
 47  \w     83.00 109.00   0.50    0.05    --   90.00  75.00 158.12   52
 48  \w     48.00  79.00   0.50    0.05    --   90.00  75.00 158.12   62
 49  \w     79.00 108.00   0.50    0.05    --   90.00  77.00 -61.02   58
 50  \w     48.00  74.00   0.50    0.05    --   90.00  77.00 -61.02   52
 51  \w     52.00  87.00   0.50    0.05    --   94.00  77.00 109.76   70
 52  \w     53.00  93.00   0.50    0.05    --   94.00  76.00-164.16   80
 53  \w     52.00  78.00   0.50    0.05    --   94.00  74.00  14.03   52
 54  \w     56.00  81.00   0.50    0.05    --   98.00  74.00 -46.51   50
 55  \w     59.00 100.00   0.50    0.05    --   98.00  69.00  66.06   82
 56  \w    144.00 170.00   0.50    0.05    --   98.00  71.00 138.29   52
 57  \w     59.00  87.00   0.50    0.05    --   98.00  71.00 138.29   56
 58  \w     60.00  89.00   0.50    0.05    --  102.00  74.00  35.03   58
 59  \w    146.00 171.00   0.50    0.05    --  106.00  71.00 -81.28   50
 60  \w     70.00  96.00   0.50    0.05    --  106.00  71.00 -81.28   52
 61  \w    133.00 159.00   0.50    0.05    --  106.00  73.00   3.71   52
 62  \w     65.00  90.00   0.50    0.05    --  106.00  73.00   3.71   50
 63  \w     71.00 101.00   0.50    0.05    --  110.00  71.00-105.91   60
 64  \w     71.00  97.00   0.50    0.05    --  110.00  70.00  95.35   52
 65  \w     68.00  99.00   0.50    0.05    --  110.00  76.00-128.76   62
 66  \w    106.00 132.00   0.50    0.05    --  110.00  70.00  95.35   52
 67  \w    108.00 176.00   0.50    0.05    --  110.00  71.00-105.91  136
 68  \w    126.00 176.00   0.50    0.05    --  114.00  71.00 -56.71  100
 69  \w     74.00 100.00   0.50    0.05    --  114.00  71.00 -56.71   52
 70  \w     78.00 141.00   0.50    0.05    --  114.00  71.00-166.27  126
 71  \w     77.00 117.00   0.50    0.05    --  118.00  48.00 -39.74   80
 72  \w     76.00 101.00   0.50    0.05    --  118.00  76.00  96.71   50
 73  \w    145.00 177.00   0.50    0.05    --  121.75  60.00 -41.00   64
 74  \w     87.00 139.00   0.50    0.05    --  121.75  60.00 -41.00  104
 75  \w     99.00 156.00   0.50    0.05    --  121.75 -60.00 179.00  114
 76  \w     47.00  93.00   0.50    0.05    --  121.75 -60.00 179.00   92
 77  \w    116.00 168.00   0.50    0.05    --  121.75  50.00  90.00  104
 78  \w     83.00 112.00   0.50    0.05    --  121.75  50.00  90.00   58
 79  \w    126.00 173.00   0.50    0.05    --  121.75 -37.00-180.00   94
 80  \w     35.00 106.00   0.50    0.05    --  121.75 -37.00-180.00  142
 81  \w     85.00 164.00   0.50    0.05    --  121.75  63.00   0.00  158
 82  \w     56.00 105.00   0.50    0.05    --  121.75 -91.00  60.00   98
 83  \w     99.00 174.00   0.50    0.05    --  121.75  63.00 -90.00  150
 84  \w     51.00 100.00   0.50    0.05    --  121.75 -91.00  30.00   98
 85  \w     86.00 139.00   0.50    0.05    --  121.75  63.00  60.00  106
 86  \w     57.00 104.00   0.50    0.05    --  121.75 -91.00-180.00   94
 87  \w     85.00 173.00   0.50    0.05    --  121.75  64.00 107.43  176
 88  \w    126.00 158.00   0.50    0.05    --  121.75  37.00-150.00   64
 89  \w     67.00  93.00   0.50    0.05    --  121.75 -91.00  90.00   52
 90  \w     74.00 100.00   0.50    0.05    --  121.75  37.00-150.00   52
 91  \w     51.00  96.00   0.50    0.05    --  121.75 -91.00 -60.00   90
 92  \w     86.00 176.00   0.50    0.05    --  121.75  65.00 -31.18  180
 93  \w     79.00 105.00   0.50    0.05    --  121.75  77.00  19.72   52
 94  \w     68.00 122.00   0.50    0.05    --  121.75 -63.00  60.00  108
 95  \w    129.00 162.00   0.50    0.05    --  121.75 -50.00 120.00   66
 96  \w     76.00 101.00   0.50    0.05    --  121.75 -50.00 120.00   50
 97  \w     40.00  66.00   0.50    0.05    --  121.75 -50.00 120.00   52
 98  \w     83.00 137.00   0.50    0.05    --  121.75  50.00 -90.00  108
 99  \w     60.00 107.00   0.50    0.05    --  121.75-104.00 165.92   94
100  \w     48.00 105.00   0.50    0.05    --  121.75 -91.00-120.00  114
101  \w    136.00 175.00   0.50    0.05    --  121.75  63.00 150.00   78
102  \w     85.00 160.00   0.50    0.05    --  121.75  63.00-150.00  150
103  \w     85.00 118.00   0.50    0.05    --  121.75  63.00-180.00   66
104  \w     98.00 160.00   0.50    0.05    --  121.75 -50.00 -60.00  124
105  \w     44.00  85.00   0.50    0.05    --  121.75 -50.00 -60.00   82
106  \w     85.00 131.00   0.50    0.05    --  121.75  63.00 150.00   92
107  \w    106.00 144.00   0.50    0.05    --  121.75 -50.00 -30.00   76
108  \w    147.00 173.00   0.50    0.05    --  121.75  63.00  60.00   52
109  \w     40.00  89.00   0.50    0.05    --  121.75 -50.00 -30.00   98
110  \w     84.00 156.00   0.50    0.05    --  121.75  50.00  30.00  144
111  \w     65.00 106.00   0.50    0.05    --  121.75 -91.00 -30.00   82
112  \w    115.00 174.00   0.50    0.05    --  121.75  37.00-180.00  118
113  \w     72.00  98.00   0.50    0.05    --  121.75  37.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0793558000
_diffrn_orient_matrix_UB_12      0.1538888000
_diffrn_orient_matrix_UB_13      -0.0381251000
_diffrn_orient_matrix_UB_21      0.1434383000
_diffrn_orient_matrix_UB_22      0.0179451000
_diffrn_orient_matrix_UB_23      -0.1010811000
_diffrn_orient_matrix_UB_31      -0.0396538000
_diffrn_orient_matrix_UB_32      -0.0183279000
_diffrn_orient_matrix_UB_33      -0.1068946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9815
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22539
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9815
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.42
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.103
_exptl_absorpt_correction_T_max  0.358
_exptl_absorpt_correction_T_min  0.021
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       block
_exptl_crystal_F_000             572.487
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         4.5500
_refine_diff_density_min         -1.5751
_refine_diff_density_rms         0.1803
_refine_ls_d_res_high            0.7899
_refine_ls_d_res_low             10.1368
_refine_ls_goodness_of_fit_ref   1.0417
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0417
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+3.8514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1798
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4461
_reflns_number_total             4573
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           42_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250153
_chemical_oxdiff_formula         'C38 H49 N3 O4 F4 I2'
_chemical_oxdiff_usercomment     '100K '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N21(H21a,H21b)
2.b Ternary CH refined with riding coordinates:
 C32(H32), C37(H37)
2.c Secondary CH2 refined with riding coordinates:
 C33(H33a,H33b), C34(H34a,H34b), C35(H35a,H35b), C36(H36a,H36b), C38(H38a,
 H38b), C39(H39a,H39b)
2.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C26(H26)
;
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.735