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_7250157
_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         'C20 H36 O6, 2(C6 H5 N3 O4)'
_chemical_formula_sum            'C32 H46 N6 O14'
_chemical_formula_weight         738.754
_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                86.229(2)
_cell_angle_beta                 80.130(1)
_cell_angle_gamma                84.865(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3820(1)
_cell_length_b                   11.4920(2)
_cell_length_c                   19.2230(3)
_cell_measurement_reflns_used    12360
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6850
_cell_measurement_theta_min      4.4020
_cell_volume                     1814.54(5)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9826
_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     20.00  70.00   0.50    0.05    --    0.00  53.00  69.00  100
  2  \w    -37.00   4.00   0.50    0.05    --    0.00  53.00  69.00   82
  3  \w     40.00  96.00   0.50    0.20    --   66.57  53.00  69.00  112
  4  \w     99.00 134.00   0.50    0.20    --   66.57  53.00  69.00   70
  5  \w     94.00 159.00   0.50    0.20    --  121.75 -53.00 -74.00  130
  6  \w     41.00  76.00   0.50    0.20    --  121.75 -53.00 -74.00   70
  7  \w    -44.00 -11.00   0.50    0.05    --    0.00 -77.00  90.00   66
  8  \w    -58.00  36.00   0.50    0.05    --    0.00 -53.00 -74.00  188
  9  \w    -82.00 -50.00   0.50    0.05    --    0.00 -77.00  90.00   64
 10  \w     50.00  78.00   0.50    0.05    --    0.00  57.00 150.00   56
 11  \w    -35.00  44.00   0.50    0.05    --    0.00  57.00 150.00  158
 12  \w    -95.00 -41.00   0.50    0.05    --    0.00-178.00 -90.00  108
 13  \w    -36.00  -5.00   0.50    0.05    --   14.00 111.00  62.69   62
 14  \w    -24.00   1.00   0.50    0.20    --   34.00 107.00   0.45   50
 15  \w      2.00  27.00   0.50    0.20    --   54.00  97.00 -77.46   50
 16  \w      2.00  27.00   0.50    0.20    --   54.00  97.00 160.01   50
 17  \w      8.00  34.00   0.50    0.20    --   58.00  93.00  38.31   52
 18  \w      7.00  32.00   0.50    0.20    --   58.00  94.00-136.63   50
 19  \w     17.00  42.00   0.50    0.20    --   62.00  87.00 173.87   50
 20  \w     15.00  42.00   0.50    0.20    --   62.00  90.00 138.49   54
 21  \w     17.00  42.00   0.50    0.20    --   66.00  90.00 -46.24   50
 22  \w     16.00  41.00   0.50    0.20    --   66.00  92.00-117.41   50
 23  \w     17.00  42.00   0.50    0.20    --   66.00  92.00 -15.11   50
 24  \w     17.00  43.00   0.50    0.20    --   66.00  90.00  74.04   52
 25  \w     16.00  41.00   0.50    0.20    --   66.00  92.00-137.71   50
 26  \w     53.00  98.00   0.50    0.20    --   66.57 -94.00   0.00   90
 27  \w     53.00 106.00   0.50    0.20    --   66.57 -94.00  60.00  106
 28  \w     52.00 104.00   0.50    0.20    --   66.57 -94.00 150.00  104
 29  \w    -22.00 130.00   0.50    0.20    --   66.57 -30.00 -60.00  304
 30  \w    -29.00 154.00   0.50    0.20    --   66.57   0.00  90.00  366
 31  \w    -12.00 103.00   0.50    0.20    --   66.57 -53.00 -74.00  230
 32  \w     56.00  86.00   0.50    0.20    --   66.57 -94.00-120.00   60
 33  \w     82.00 107.00   0.50    0.20    --   70.00  75.00-120.86   50
 34  \w     31.00  64.00   0.50    0.20    --   70.00  75.00-120.86   66
 35  \w     84.00 109.00   0.50    0.20    --   74.00  76.00 -96.58   50
 36  \w     75.00 109.00   0.50    0.20    --   74.00  77.00 -32.52   68
 37  \w     31.00  58.00   0.50    0.20    --   74.00  77.00 -32.52   54
 38  \w     36.00  62.00   0.50    0.20    --   74.00  76.00 -96.58   52
 39  \w     31.00  63.00   0.50    0.20    --   74.00  77.00 148.99   64
 40  \w     36.00  61.00   0.50    0.20    --   78.00  74.00   5.20   50
 41  \w     84.00 109.00   0.50    0.20    --   82.00  76.00 -78.98   50
 42  \w     40.00  77.00   0.50    0.20    --   82.00  76.00 160.96   74
 43  \w     40.00  65.00   0.50    0.20    --   82.00  76.00 -78.98   50
 44  \w     39.00  85.00   0.50    0.20    --   82.00  77.00  76.57   92
 45  \w     40.00  67.00   0.50    0.20    --   82.00  77.00-172.43   54
 46  \w     44.00  70.00   0.50    0.20    --   86.00  76.00 109.10   52
 47  \w     45.00  71.00   0.50    0.20    --   86.00  76.00-142.67   52
 48  \w     44.00  69.00   0.50    0.20    --   86.00  74.00 -37.86   50
 49  \w     48.00  73.00   0.50    0.20    --   90.00  75.00  24.20   50
 50  \w     51.00  77.00   0.50    0.20    --   90.00  77.00  40.93   52
 51  \w     48.00  75.00   0.50    0.20    --   90.00  74.00-125.92   54
 52  \w     48.00  74.00   0.50    0.20    --   90.00  76.00   0.63   52
 53  \w    130.00 156.00   0.50    0.20    --   94.00  72.00 -14.77   52
 54  \w     54.00  95.00   0.50    0.20    --   94.00  77.00  63.76   82
 55  \w     52.00  78.00   0.50    0.20    --   94.00  77.00 106.94   52
 56  \w     53.00  78.00   0.50    0.20    --   94.00  72.00 -14.77   50
 57  \w    128.00 154.00   0.50    0.20    --   94.00  68.00-161.33   52
 58  \w     55.00  81.00   0.50    0.20    --   94.00  68.00-161.33   52
 59  \w     52.00  78.00   0.50    0.20    --   94.00  76.00 146.81   52
 60  \w     52.00  78.00   0.50    0.20    --   94.00  75.00-111.45   52
 61  \w     52.00 109.00   0.50    0.20    --   94.00  75.00 -73.64  114
 62  \w     56.00  81.00   0.50    0.20    --   98.00  74.00 -10.49   50
 63  \w    124.00 176.00   0.50    0.20    --   98.00  70.00  32.97  104
 64  \w    111.00 177.00   0.50    0.20    --   98.00  71.00 -46.38  132
 65  \w     58.00  83.00   0.50    0.20    --   98.00  71.00 -46.38   50
 66  \w     58.00 101.00   0.50    0.20    --   98.00  70.00  32.97   86
 67  \w     62.00  91.00   0.50    0.20    --  102.00  76.00  42.68   58
 68  \w    121.00 170.00   0.50    0.20    --  102.00  71.00-122.72   98
 69  \w     62.00  88.00   0.50    0.20    --  102.00  71.00-122.72   52
 70  \w     60.00 103.00   0.50    0.20    --  102.00  74.00 115.00   86
 71  \w     60.00 106.00   0.50    0.20    --  102.00  75.00   6.83   92
 72  \w     63.00  88.00   0.50    0.20    --  106.00  77.00-163.03   50
 73  \w     64.00  90.00   0.50    0.20    --  106.00  74.00 155.04   52
 74  \w    134.00 160.00   0.50    0.20    --  106.00  70.00 142.04   52
 75  \w     66.00  92.00   0.50    0.20    --  106.00  70.00 142.04   52
 76  \w     65.00 109.00   0.50    0.20    --  106.00  75.00-175.74   88
 77  \w     64.00  89.00   0.50    0.20    --  106.00  74.00 -60.20   50
 78  \w    141.00 177.00   0.50    0.20    --  110.00  62.00-108.92   72
 79  \w     75.00 101.00   0.50    0.20    --  110.00  62.00-108.92   52
 80  \w    109.00 178.00   0.50    0.20    --  114.00  67.00 165.02  138
 81  \w     76.00 101.00   0.50    0.20    --  114.00  67.00 165.02   50
 82  \w     72.00  97.00   0.50    0.20    --  114.00  76.00-118.20   50
 83  \w     74.00 105.00   0.50    0.20    --  121.75 -91.00 -30.00   62
 84  \w    125.00 151.00   0.50    0.20    --  121.75  50.00   0.00   52
 85  \w    107.00 144.00   0.50    0.20    --  121.75 -50.00-180.00   74
 86  \w    119.00 178.00   0.50    0.20    --  121.75  63.00 -60.00  118
 87  \w     86.00 113.00   0.50    0.20    --  121.75  63.00 -60.00   54
 88  \w     80.00 108.00   0.50    0.20    --  121.75  75.00-115.86   56
 89  \w     39.00  81.00   0.50    0.20    --  121.75 -50.00-180.00   84
 90  \w    129.00 170.00   0.50    0.20    --  121.75  70.00 102.09   82
 91  \w     82.00 122.00   0.50    0.20    --  121.75  70.00 102.09   80
 92  \w     46.00 101.00   0.50    0.20    --  121.75 -91.00  60.00  110
 93  \w     64.00 108.00   0.50    0.20    --  121.75-107.00 -52.80   88
 94  \w    111.00 154.00   0.50    0.20    --  121.75 -63.00 120.00   86
 95  \w     85.00 168.00   0.50    0.20    --  121.75  63.00 -90.00  166
 96  \w     65.00  91.00   0.50    0.20    --  121.75 -63.00 120.00   52
 97  \w     90.00 174.00   0.50    0.20    --  121.75  57.00  40.61  168
 98  \w    121.00 177.00   0.50    0.20    --  121.75  40.00 179.36  112
 99  \w    114.00 140.00   0.50    0.20    --  121.75  46.00 108.26   52
100  \w     79.00 106.00   0.50    0.20    --  121.75  46.00 108.26   54
101  \w    124.00 178.00   0.50    0.20    --  121.75  63.00  60.00  108
102  \w     87.00 113.00   0.50    0.20    --  121.75  63.00  60.00   52
103  \w     79.00 105.00   0.50    0.20    --  121.75  76.00 161.98   52
104  \w     47.00  88.00   0.50    0.20    --  121.75 -91.00 -90.00   82
105  \w    142.00 177.00   0.50    0.20    --  121.75  53.00  69.00   70
106  \w     87.00 137.00   0.50    0.20    --  121.75  63.00 -30.00  100
107  \w     46.00 103.00   0.50    0.20    --  121.75 -91.00 150.00  114
108  \w     66.00 108.00   0.50    0.20    --  121.75-110.00  67.89   84
109  \w    126.00 178.00   0.50    0.20    --  121.75  50.00-120.00  104
110  \w     46.00 106.00   0.50    0.20    --  121.75 -91.00  90.00  120
111  \w     47.00 105.00   0.50    0.20    --  121.75 -91.00 -60.00  116
112  \w     83.00 119.00   0.50    0.20    --  121.75  50.00-120.00   72
113  \w     63.00 107.00   0.50    0.20    --  121.75-101.00-154.82   88
114  \w     85.00 175.00   0.50    0.20    --  121.75  63.00-150.00  180
115  \w     82.00 177.00   0.50    0.20    --  121.75  71.00 132.09  190
116  \w     86.00 112.00   0.50    0.20    --  121.75  63.00  90.00   52
117  \w     96.00 147.00   0.50    0.20    --  121.75 -37.00  60.00  102
118  \w     42.00  82.00   0.50    0.20    --  121.75 -37.00  60.00   80
119  \w     82.00 107.00   0.50    0.20    --  121.75  74.00 -17.46   50
120  \w     89.00 178.00   0.50    0.20    --  121.75  68.00   1.42  178
121  \w     98.00 123.00   0.50    0.20    --  121.75-140.00 -24.41   50
122  \w     87.00 176.00   0.50    0.20    --  121.75  63.00 120.00  178
123  \w     81.00 108.00   0.50    0.20    --  121.75  75.00   8.73   54
124  \w     50.00  78.00   0.50    0.20    --  121.75 -91.00   0.00   56
125  \w    135.00 176.00   0.50    0.20    --  121.75  50.00 -30.00   82
126  \w     83.00 108.00   0.50    0.20    --  121.75  77.00 169.59   50
127  \w    136.00 162.00   0.50    0.20    --  121.75  72.00 -77.12   52
128  \w     88.00 114.00   0.50    0.20    --  121.75  50.00   0.00   52
129  \w     54.00  94.00   0.50    0.20    --  121.75 -91.00 120.00   80
130  \w     80.00 118.00   0.50    0.20    --  121.75  72.00 -77.12   76
131  \w     86.00 117.00   0.50    0.20    --  121.75  50.00 -30.00   62
132  \w     84.00 118.00   0.50    0.20    --  121.75  53.00  69.00   68
;
_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      0.0490448000
_diffrn_orient_matrix_UB_12      0.0798496000
_diffrn_orient_matrix_UB_13      0.0527763000
_diffrn_orient_matrix_UB_21      0.1635337000
_diffrn_orient_matrix_UB_22      -0.0736285000
_diffrn_orient_matrix_UB_23      -0.0022931000
_diffrn_orient_matrix_UB_31      0.0766674000
_diffrn_orient_matrix_UB_32      0.0797912000
_diffrn_orient_matrix_UB_33      -0.0620009000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9826
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42169
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9826
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.75
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_correction_T_min  0.285
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             787.088
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.5127
_refine_diff_density_min         -0.4048
_refine_diff_density_rms         0.0562
_refine_ls_d_res_high            0.7889
_refine_ls_d_res_low             11.4308
_refine_ls_goodness_of_fit_ref   1.0473
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    68
_refine_ls_number_parameters     485
_refine_ls_number_reflns         7616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0473
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+1.5077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                6603
_reflns_number_total             7616
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           43_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250157
_chemical_oxdiff_formula         'C36 H49 N3 O4 F9 I1'
_chemical_oxdiff_usercomment     '100K '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00S(H00S), C00V(H00V), C00Z(H00Z), C013(H013)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00a,H00b), C00W(H00c,H00d), C00X(H00e,H00f), C010(H01a,H01b), C011(H01c,
 H01d), C012(H01e,H01f), C014(H01g,H01h), C016(H01i,H01j), C017(H01k,H01l),
 C019(H01m,H01n), C01A(H01o,H01p), C01B(H01q,H01r), C01C(H01s,H01t), C01D(H01u,
 H01v), C01E(H01w,H01x), C01F(H01y,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00i), C00L(H00L), C00O(H00O), C00P(H00P), C00T(H00T), C01G(H01z)
;
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.698