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_7250159
_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         '2(C6 H5 N3 O4), C20 H36 O6'
_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                104.953(1)
_cell_angle_beta                 91.171(1)
_cell_angle_gamma                95.137(1)
_cell_formula_units_Z            4
_cell_length_a                   11.5000(1)
_cell_length_b                   16.7610(2)
_cell_length_c                   19.5890(2)
_cell_measurement_reflns_used    61739
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      77.6170
_cell_measurement_theta_min      3.8840
_cell_volume                     3629.58(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      99.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9869
_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    -71.00  19.00   0.50    1.00    --    0.00 -31.00  70.00  180
  2  \w     29.00  54.00   0.50    1.00    --    0.00 -31.00  70.00   50
  3  \w    -89.00 -45.00   0.50    1.00    --    0.00-178.00  60.00   88
  4  \w    -42.00 -11.00   0.50    1.00    --    0.00 -77.00-180.00   62
  5  \w    -76.00 -46.00   0.50    1.00    --    0.00 -77.00-180.00   60
  6  \w    -51.00  77.00   0.50    1.00    --    0.00  31.00-129.00  256
  7  \w    -35.00  61.00   0.50    1.00    --    0.00  57.00 -60.00  192
  8  \w    -30.00   3.00   0.50    1.00    --   26.00 106.00  14.57   66
  9  \w    -36.00 -11.00   0.50    1.00    --   30.00 122.00  84.15   50
 10  \w      1.00  39.00   0.50    1.00    --   42.00  92.00-133.81   76
 11  \w      1.00  26.00   0.50    1.00    --   54.00  98.00  61.40   50
 12  \w      2.00  27.00   0.50    1.00    --   54.00  96.00-158.09   50
 13  \w      8.00  33.00   0.50    1.00    --   58.00  93.00 139.85   50
 14  \w      8.00  34.00   0.50    1.00    --   58.00  94.00-113.27   52
 15  \w     17.00  42.00   0.50    1.00    --   62.00  92.00  36.99   50
 16  \w     16.00  41.00   0.50    1.00    --   66.00  92.00-163.35   50
 17  \w     17.00  42.00   0.50    1.00    --   66.00  90.00 -76.28   50
 18  \w     16.00  41.00   0.50    1.00    --   66.00  92.00 -53.84   50
 19  \w     17.00  42.00   0.50    1.00    --   66.00  90.00  -8.79   50
 20  \w     18.00  43.00   0.50    1.00    --   66.00  90.00-116.99   50
 21  \w     16.00  41.00   0.50    1.00    --   66.00  92.00  11.38   50
 22  \w     17.00  42.00   0.50    1.00    --   66.00  90.00 159.92   50
 23  \w     16.00  41.00   0.50    1.00    --   66.00  92.00  94.03   50
 24  \w    -21.00 131.00   0.50    1.00    --   66.57 -31.00  70.00  304
 25  \w     67.00 139.00   0.50    1.00    --   66.57  31.00-129.00  144
 26  \w     11.00  58.00   0.50    1.00    --   66.57  31.00-129.00   94
 27  \w     56.00  97.00   0.50    1.00    --   66.57 -94.00-120.00   82
 28  \w     52.00 102.00   0.50    1.00    --   66.57 -94.00-180.00  100
 29  \w     30.00 109.00   0.50    1.00    --   66.57  75.00  84.23  158
 30  \w     29.00 100.00   0.50    1.00    --   66.57 -77.00 -90.00  142
 31  \w     -5.00  32.00   0.50    1.00    --   66.57 -61.00-180.00   74
 32  \w     57.00  99.00   0.50    1.00    --   66.57 -94.00 -30.00   84
 33  \w     39.00 101.00   0.50    1.00    --   66.57 -61.00-180.00  124
 34  \w    -11.00 103.00   0.50    1.00    --   66.57 -61.00  60.00  228
 35  \w     35.00  68.00   0.50    1.00    --   78.00  77.00  14.09   66
 36  \w     35.00  61.00   0.50    1.00    --   78.00  77.00 149.72   52
 37  \w     35.00  63.00   0.50    1.00    --   78.00  77.00-161.24   56
 38  \w     73.00 109.00   0.50    1.00    --   78.00  77.00 149.72   72
 39  \w     39.00  69.00   0.50    1.00    --   78.00  74.00  98.41   60
 40  \w     36.00  72.00   0.50    1.00    --   78.00  76.00 -43.20   72
 41  \w     82.00 108.00   0.50    1.00    --   78.00  77.00 119.57   52
 42  \w     35.00  60.00   0.50    1.00    --   78.00  77.00 -96.28   50
 43  \w     83.00 108.00   0.50    1.00    --   78.00  77.00-161.24   50
 44  \w     35.00  74.00   0.50    1.00    --   78.00  77.00 119.57   78
 45  \w     39.00  88.00   0.50    1.00    --   82.00  77.00 -73.61   98
 46  \w     43.00  77.00   0.50    1.00    --   86.00  77.00  33.85   68
 47  \w     84.00 109.00   0.50    1.00    --   86.00  77.00-139.41   50
 48  \w     43.00  74.00   0.50    1.00    --   86.00  77.00  70.35   62
 49  \w     43.00  77.00   0.50    1.00    --   86.00  77.00 -27.28   68
 50  \w     79.00 104.00   0.50    1.00    --   86.00  77.00  33.85   50
 51  \w     44.00  70.00   0.50    1.00    --   86.00  75.00  17.33   52
 52  \w     43.00  75.00   0.50    1.00    --   86.00  77.00-139.41   64
 53  \w     84.00 109.00   0.50    1.00    --   86.00  77.00 160.83   50
 54  \w     43.00  69.00   0.50    1.00    --   86.00  77.00 160.83   52
 55  \w     43.00  68.00   0.50    1.00    --   86.00  77.00  52.67   50
 56  \w     49.00  74.00   0.50    1.00    --   90.00  76.00 -79.63   50
 57  \w    105.00 133.00   0.50    1.00    --   90.00  73.00  20.55   56
 58  \w    105.00 169.00   0.50    1.00    --   90.00  72.00 130.93  128
 59  \w     49.00  74.00   0.50    1.00    --   90.00  73.00  20.55   50
 60  \w     48.00  74.00   0.50    1.00    --   90.00  76.00  40.35   52
 61  \w     49.00  75.00   0.50    1.00    --   90.00  72.00 130.93   52
 62  \w     52.00  97.00   0.50    1.00    --   94.00  74.00-120.50   90
 63  \w     84.00 109.00   0.50    1.00    --   94.00  74.00  92.75   50
 64  \w     52.00  78.00   0.50    1.00    --   94.00  74.00  92.75   52
 65  \w     52.00  77.00   0.50    1.00    --   94.00  74.00-163.63   50
 66  \w     52.00  77.00   0.50    1.00    --   94.00  74.00 -57.69   50
 67  \w     55.00  82.00   0.50    1.00    --   94.00  76.00 -21.75   54
 68  \w     52.00  78.00   0.50    1.00    --   94.00  76.00 165.88   52
 69  \w     52.00  87.00   0.50    1.00    --   94.00  76.00  52.45   70
 70  \w     55.00  80.00   0.50    1.00    --   98.00  77.00-110.45   50
 71  \w     57.00 100.00   0.50    1.00    --   98.00  75.00 -40.02   86
 72  \w     56.00  85.00   0.50    1.00    --   98.00  76.00-147.80   58
 73  \w     62.00 119.00   0.50    1.00    --  102.00  73.00  52.21  114
 74  \w    122.00 148.00   0.50    1.00    --  102.00  73.00  52.21   52
 75  \w     60.00  85.00   0.50    1.00    --  102.00  76.00 116.89   50
 76  \w     60.00  87.00   0.50    1.00    --  102.00  75.00-147.17   54
 77  \w    128.00 154.00   0.50    1.00    --  106.00  73.00 -69.81   52
 78  \w     66.00 153.00   0.50    1.00    --  106.00  71.00  79.86  174
 79  \w     66.00  97.00   0.50    1.00    --  106.00  73.00 -69.81   62
 80  \w     64.00 106.00   0.50    1.00    --  106.00  76.00 -47.71   84
 81  \w    116.00 142.00   0.50    1.00    --  106.00  64.00  13.56   52
 82  \w     69.00  95.00   0.50    1.00    --  106.00  64.00  13.56   52
 83  \w     64.00  89.00   0.50    1.00    --  106.00  75.00 165.80   50
 84  \w     71.00  97.00   0.50    1.00    --  110.00  70.00 -88.37   52
 85  \w    143.00 177.00   0.50    1.00    --  110.00  72.00-178.05   68
 86  \w     69.00 100.00   0.50    1.00    --  110.00  72.00-178.05   62
 87  \w    138.00 164.00   0.50    1.00    --  110.00  70.00 -88.37   52
 88  \w     67.00  92.00   0.50    1.00    --  110.00  77.00 126.22   50
 89  \w    112.00 161.00   0.50    1.00    --  110.00  72.00 139.53   98
 90  \w     70.00  96.00   0.50    1.00    --  110.00  72.00 139.53   52
 91  \w     71.00  96.00   0.50    1.00    --  114.00  77.00-144.39   50
 92  \w     71.00 108.00   0.50    1.00    --  114.00  77.00-159.37   74
 93  \w     72.00 101.00   0.50    1.00    --  114.00  76.00 -31.94   58
 94  \w     72.00 107.00   0.50    1.00    --  114.00  75.00  89.63   70
 95  \w     74.00 160.00   0.50    1.00    --  114.00  73.00  51.01  172
 96  \w     77.00 105.00   0.50    1.00    --  118.00  76.00-172.24   56
 97  \w     76.00 102.00   0.50    1.00    --  118.00  76.00 -26.70   52
 98  \w     83.00 174.00   0.50    1.00    --  118.00  57.00-110.80  182
 99  \w     81.00 170.00   0.50    1.00    --  118.00  71.00-145.84  178
100  \w    130.00 156.00   0.50    1.00    --  118.00  61.00-104.04   52
101  \w     82.00 117.00   0.50    1.00    --  118.00  61.00-104.04   70
102  \w     35.00  76.00   0.50    1.00    --  121.75 -31.00  70.00   82
103  \w     60.00 106.00   0.50    1.00    --  121.75 -97.00  51.81   92
104  \w     58.00 107.00   0.50    1.00    --  121.75-101.00-117.77   98
105  \w    137.00 176.00   0.50    1.00    --  121.75  70.00   5.33   78
106  \w    106.00 162.00   0.50    1.00    --  121.75  63.00-180.00  112
107  \w     82.00 133.00   0.50    1.00    --  121.75  70.00   5.33  102
108  \w     93.00 118.00   0.50    1.00    --  121.75  25.00 -90.00   50
109  \w     38.00  80.00   0.50    1.00    --  121.75  25.00 -90.00   84
110  \w     46.00 103.00   0.50    1.00    --  121.75 -91.00  90.00  114
111  \w     46.00 106.00   0.50    1.00    --  121.75 -91.00   0.00  120
112  \w     90.00 173.00   0.50    1.00    --  121.75  63.00 -30.00  166
113  \w     94.00 126.00   0.50    1.00    --  121.75-143.00  53.81   64
114  \w     87.00 178.00   0.50    1.00    --  121.75  63.00   0.00  182
115  \w     79.00 109.00   0.50    1.00    --  121.75  77.00 149.41   60
116  \w    141.00 177.00   0.50    1.00    --  121.75  63.00 116.32   72
117  \w    103.00 161.00   0.50    1.00    --  121.75 -50.00 -60.00  116
118  \w     39.00  80.00   0.50    1.00    --  121.75 -50.00 -60.00   82
119  \w     78.00 103.00   0.50    1.00    --  121.75 -91.00 -90.00   50
120  \w     85.00 134.00   0.50    1.00    --  121.75  63.00 116.32   98
121  \w    149.00 178.00   0.50    1.00    --  121.75  25.00 -90.00   58
122  \w     59.00 107.00   0.50    1.00    --  121.75-101.00 -82.04   96
123  \w     83.00 160.00   0.50    1.00    --  121.75  69.00 -71.74  154
124  \w     51.00  77.00   0.50    1.00    --  121.75 -91.00 -90.00   52
125  \w    129.00 174.00   0.50    1.00    --  121.75  31.00-129.00   90
126  \w    116.00 175.00   0.50    1.00    --  121.75  70.00  65.21  118
127  \w    104.00 136.00   0.50    1.00    --  121.75 -50.00  90.00   64
128  \w     83.00 113.00   0.50    1.00    --  121.75  70.00  65.21   60
129  \w     51.00  82.00   0.50    1.00    --  121.75 -91.00-150.00   62
130  \w     44.00 101.00   0.50    1.00    --  121.75 -50.00  90.00  114
131  \w    126.00 163.00   0.50    1.00    --  121.75  43.00 112.92   74
132  \w    147.00 176.00   0.50    1.00    --  121.75  73.00  23.11   58
133  \w     81.00 135.00   0.50    1.00    --  121.75  73.00  23.11  108
134  \w     77.00 105.00   0.50    1.00    --  121.75 -91.00-180.00   56
135  \w    131.00 177.00   0.50    1.00    --  121.75  50.00 150.00   92
136  \w     88.00 127.00   0.50    1.00    --  121.75  50.00 150.00   78
137  \w     72.00 167.00   0.50    1.00    --  121.75 -88.00 -39.98  190
138  \w     80.00 109.00   0.50    1.00    --  121.75  75.00 163.68   58
139  \w     46.00  73.00   0.50    1.00    --  121.75 -91.00-180.00   54
140  \w     79.00 104.00   0.50    1.00    --  121.75  77.00   7.44   50
141  \w     83.00 170.00   0.50    1.00    --  121.75  67.00  42.45  174
142  \w    130.00 161.00   0.50    1.00    --  121.75 -50.00-120.00   62
143  \w    101.00 160.00   0.50    1.00    --  121.75 -50.00 -90.00  118
144  \w     40.00 106.00   0.50    1.00    --  121.75 -50.00-120.00  132
145  \w     71.00 107.00   0.50    1.00    --  121.75-102.00 112.87   72
146  \w     56.00 106.00   0.50    1.00    --  121.75 -98.00 148.98  100
147  \w     48.00  74.00   0.50    1.00    --  121.75 -50.00 -90.00   52
148  \w    135.00 177.00   0.50    1.00    --  121.75  50.00 -60.00   84
149  \w     82.00 120.00   0.50    1.00    --  121.75  50.00 -60.00   76
150  \w     85.00 147.00   0.50    1.00    --  121.75  54.00 -29.68  124
151  \w    143.00 172.00   0.50    1.00    --  121.75  72.00  86.02   58
152  \w     81.00 127.00   0.50    1.00    --  121.75  72.00  86.02   92
153  \w    141.00 166.00   0.50    1.00    --  121.75 -31.00  70.00   50
154  \w     82.00 122.00   0.50    1.00    --  121.75 -31.00  70.00   80
;
_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      -0.0661714000
_diffrn_orient_matrix_UB_12      0.0618050000
_diffrn_orient_matrix_UB_13      -0.0280989000
_diffrn_orient_matrix_UB_21      0.1095634000
_diffrn_orient_matrix_UB_22      0.0629242000
_diffrn_orient_matrix_UB_23      0.0160829000
_diffrn_orient_matrix_UB_31      0.0417911000
_diffrn_orient_matrix_UB_32      -0.0368757000
_diffrn_orient_matrix_UB_33      -0.0747784000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9869
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            99456
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9869
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.68
_diffrn_reflns_theta_min         3.86
_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  0.331
_exptl_absorpt_correction_T_min  0.087
_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             1574.176
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.5031
_refine_diff_density_min         -0.3167
_refine_diff_density_rms         0.0438
_refine_ls_d_res_high            0.7891
_refine_ls_d_res_low             11.4417
_refine_ls_goodness_of_fit_ref   1.0377
_refine_ls_matrix_type           full
_refine_ls_number_constraints    147
_refine_ls_number_parameters     944
_refine_ls_number_reflns         15273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0377
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+0.8063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1500
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              20
_reflns_limit_k_min              -21
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                13540
_reflns_number_total             15273
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           44_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250159
_chemical_oxdiff_formula         'C36 H49 N3 O4 F8 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) groups, All N(H,H) groups
2.a Rotating group:
 N11(H11a,H11b), N21(H21a), N31(H31a,H31b), N41(H41a,H41b)
2.b Ternary CH refined with riding coordinates:
 C51(H51), C56(H56), C61(H61), C66(H66), C71(H71), C76(H76), C81(H81), C86(H86)
2.c Secondary CH2 refined with riding coordinates:
 C52(H52a,H52b), C53(H53a,H53b), C54(H54a,H54b), C55(H55a,H55b), C58(H58a,
 H58b), C59(H59a,H59b), C62(H62a,H62b), C63(H63a,H63b), C64(H64a,H64b),
 C65(H65a,H65b), C68(H68a,H68b), C69(H69a,H69b), C70(H70a,H70b), C72(H72a,H72b),
  C73(H73a,H73b), C74(H74a,H74b), C75(H75a,H75b), C77(H77a,H77b), C78(H78a,
 H78b), C79(H79a,H79b), C80(H80a,H80b), C82(H82a,H82b), C83(H83a,H83b),
 C84(H84a,H84b), C85(H85a,H85b), C87(H87a,H87b), C88(H88a,H88b), C89(H89a,H89b),
  C90(H90a,H90b), C67(H67a,H67b), C60(H60a,H60b), C57(H57a,H57b)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C16(H16), C22(H22), C24(H24), C26(H26), C32(H32),
 C34(H34), C36(H36), C42(H42), C44(H44), C46(H46)
;
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.647