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_7250155
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_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                90
_cell_angle_beta                 99.410(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5430(1)
_cell_length_b                   11.8220(1)
_cell_length_c                   20.0720(2)
_cell_measurement_reflns_used    16565
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.4040
_cell_measurement_theta_min      4.4690
_cell_volume                     1765.80(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_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 1.0000
_diffrn_measured_fraction_theta_max 0.9958
_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    -59.00 -17.00   0.50    0.05    --    0.00 124.00 156.00   84
  2  \w    -77.00 -29.00   0.50    0.05    --    0.00 147.00 -37.00   96
  3  \w     98.00 123.00   0.50    0.50    --   66.54 124.00 156.00   50
  4  \w     68.00 125.00   0.50    0.50    --   66.54-147.00 -87.00  114
  5  \w     42.00  90.00   0.50    0.50    --   66.54-124.00  77.00   96
  6  \w     81.00 121.00   0.50    0.50    --   66.54 147.00 -37.00   80
  7  \w     64.00  90.00   0.50    0.60    --  121.75-124.00  77.00   52
  8  \w    100.00 125.00   0.50    0.60    --  121.75 147.00 -37.00   50
  9  \w     78.00 126.00   0.50    0.60    --  121.75-147.00 -87.00   96
 10  \w     96.00 131.00   0.50    0.60    --  121.75 124.00 156.00   70
 11  \w    -23.00  32.00   0.50    0.05    --    0.00 -57.00  60.00  110
 12  \w    -16.00  12.00   0.50    0.05    --    0.00  77.00 -30.00   56
 13  \w    -79.00 -17.00   0.50    0.05    --    0.00 -57.00   0.00  124
 14  \w     27.00  85.00   0.50    0.05    --    0.00  77.00 -30.00  116
 15  \w     -2.00  29.00   0.50    0.05    --    0.00 -57.00   0.00   62
 16  \w    -48.00  35.00   0.50    0.05    --    0.00 -57.00 -90.00  166
 17  \w    -78.00 -29.00   0.50    0.05    --    0.00 -57.00  60.00   98
 18  \w    -77.00 -52.00   0.50    0.05    --    0.00 -57.00 -90.00   50
 19  \w    -33.00  -5.00   0.50    0.05    --   26.00 114.00 -73.10   56
 20  \w     -2.00  23.00   0.50    0.50    --   50.00  98.00-101.22   50
 21  \w      8.00  33.00   0.50    0.50    --   58.00  92.00 102.97   50
 22  \w     13.00  38.00   0.50    0.50    --   62.00  91.00 152.03   50
 23  \w     13.00  38.00   0.50    0.50    --   62.00  91.00 -79.20   50
 24  \w     13.00  38.00   0.50    0.50    --   62.00  91.00  12.60   50
 25  \w     13.00  41.00   0.50    0.50    --   62.00  92.00 -48.21   56
 26  \w     17.00  42.00   0.50    0.50    --   66.00  90.00   0.03   50
 27  \w     17.00  42.00   0.50    0.50    --   66.00  90.00  82.73   50
 28  \w     17.00  42.00   0.50    0.50    --   66.00  90.00  35.40   50
 29  \w     26.00  52.00   0.50    0.50    --   66.54  77.00 -60.00   52
 30  \w     29.00 151.00   0.50    0.50    --   66.54  77.00 150.00  244
 31  \w     56.00 152.00   0.50    0.50    --   66.54  77.00 -60.00  192
 32  \w     34.00 111.00   0.50    0.50    --   66.54-125.00   0.00  154
 33  \w     76.00 155.00   0.50    0.50    --   70.00  75.00-143.11  158
 34  \w     27.00 156.00   0.50    0.50    --   70.00  77.00  43.21  258
 35  \w     28.00  53.00   0.50    0.50    --   70.00  75.00-143.11   50
 36  \w     31.00  64.00   0.50    0.50    --   74.00  77.00-123.80   66
 37  \w    100.00 126.00   0.50    0.50    --   74.00  77.00-123.80   52
 38  \w     70.00  96.00   0.50    0.50    --   74.00  77.00-123.80   52
 39  \w     31.00  83.00   0.50    0.50    --   74.00  76.00  83.50  104
 40  \w    132.00 159.00   0.50    0.50    --   78.00  73.00 -71.37   54
 41  \w     35.00  61.00   0.50    0.50    --   78.00  76.00-174.61   52
 42  \w     37.00  62.00   0.50    0.50    --   78.00  72.00 113.85   50
 43  \w    106.00 155.00   0.50    0.50    --   78.00  72.00 113.85   98
 44  \w     38.00  69.00   0.50    0.50    --   78.00  70.00  20.07   62
 45  \w     90.00 115.00   0.50    0.50    --   78.00  70.00  20.07   50
 46  \w     72.00  98.00   0.50    0.50    --   78.00  72.00 113.85   52
 47  \w     37.00 126.00   0.50    0.50    --   78.00  73.00 -71.37  178
 48  \w    140.00 166.00   0.50    0.50    --   82.00  77.00-101.84   52
 49  \w     39.00  65.00   0.50    0.50    --   82.00  77.00-101.84   52
 50  \w     40.00  71.00   0.50    0.50    --   82.00  74.00 157.20   62
 51  \w     90.00 137.00   0.50    0.50    --   86.00  75.00-136.53   94
 52  \w     44.00 147.00   0.50    0.50    --   86.00  77.00  15.09  206
 53  \w     43.00  68.00   0.50    0.50    --   86.00  77.00 176.65   50
 54  \w     45.00  81.00   0.50    0.50    --   86.00  75.00-136.53   72
 55  \w     48.00  73.00   0.50    0.50    --   90.00  75.00-171.10   50
 56  \w     49.00  75.00   0.50    0.50    --   90.00  75.00  39.97   52
 57  \w     50.00 112.00   0.50    0.50    --   90.00  74.00 118.26  124
 58  \w    105.00 130.00   0.50    0.50    --   90.00  76.00 -53.75   50
 59  \w    149.00 174.00   0.50    0.50    --   90.00  76.00 -53.75   50
 60  \w     47.00  81.00   0.50    0.50    --   90.00  76.00 -53.75   68
 61  \w     50.00  76.00   0.50    0.50    --   90.00  71.00-103.55   52
 62  \w     58.00  83.00   0.50    0.50    --   94.00  63.00 -78.83   50
 63  \w    101.00 149.00   0.50    0.50    --   94.00  77.00 -28.08   96
 64  \w     52.00  78.00   0.50    0.50    --   94.00  77.00 -28.08   52
 65  \w    125.00 177.00   0.50    0.50    --   94.00  77.00  89.94  104
 66  \w     51.00  86.00   0.50    0.50    --   94.00  77.00  89.94   70
 67  \w    137.00 178.00   0.50    0.60    --  102.00  70.00-138.98   82
 68  \w     67.00  93.00   0.50    0.60    --  102.00  70.00-138.98   52
 69  \w     65.00  95.00   0.50    0.60    --  102.00  72.00-155.51   60
 70  \w    143.00 170.00   0.50    0.60    --  102.00  73.00 171.22   54
 71  \w     61.00  87.00   0.50    0.60    --  102.00  73.00 171.22   52
 72  \w    135.00 161.00   0.50    0.60    --  106.00  71.00  52.57   52
 73  \w     67.00  98.00   0.50    0.60    --  106.00  71.00  52.57   62
 74  \w     72.00 150.00   0.50    0.60    --  110.00  67.00 -80.91  156
 75  \w    114.00 178.00   0.50    0.60    --  114.00  69.00-179.68  128
 76  \w    131.00 167.00   0.50    0.60    --  114.00  74.00  27.13   72
 77  \w     72.00 117.00   0.50    0.60    --  114.00  74.00  27.13   90
 78  \w     74.00  99.00   0.50    0.60    --  114.00  69.00-179.68   50
 79  \w     38.00 108.00   0.50    0.60    --  121.75-111.00-180.00  140
 80  \w     80.00 135.00   0.50    0.60    --  121.75  77.00-150.00  110
 81  \w    113.00 168.00   0.50    0.60    --  121.75 -87.00  27.23  110
 82  \w    151.00 177.00   0.50    0.60    --  121.75  77.00-120.00   52
 83  \w     36.00  94.00   0.50    0.60    --  121.75 -87.00  27.23  116
 84  \w     86.00 175.00   0.50    0.60    --  121.75  77.00  30.00  178
 85  \w     80.00 146.00   0.50    0.60    --  121.75  77.00-120.00  132
 86  \w    111.00 171.00   0.50    0.60    --  121.75  77.00 -60.00  120
 87  \w     87.00 120.00   0.50    0.60    --  121.75  63.00 120.00   66
 88  \w     46.00 104.00   0.50    0.60    --  121.75-111.00  90.00  116
 89  \w     40.00 108.00   0.50    0.60    --  121.75-111.00-120.00  136
 90  \w     49.00 108.00   0.50    0.60    --  121.75-111.00 -90.00  118
 91  \w     86.00 167.00   0.50    0.60    --  121.75  64.00  84.61  162
 92  \w     85.00 149.00   0.50    0.60    --  121.75  63.00 -60.00  128
 93  \w     45.00 108.00   0.50    0.60    --  121.75-111.00 120.00  126
 94  \w     88.00 157.00   0.50    0.60    --  121.75  63.00 -90.00  138
 95  \w     79.00 105.00   0.50    0.60    --  121.75  77.00 -60.00   52
 96  \w    122.00 155.00   0.50    0.60    --  121.75  76.00 -37.73   66
 97  \w    145.00 176.00   0.50    0.60    --  121.75  77.00  90.00   62
 98  \w     81.00 107.00   0.50    0.60    --  121.75  76.00 -37.73   52
 99  \w     81.00 108.00   0.50    0.60    --  121.75  77.00  90.00   54
100  \w    125.00 178.00   0.50    0.60    --  121.75  77.00  60.00  106
101  \w     74.00 104.00   0.50    0.60    --  121.75 -91.00 -30.00   60
102  \w     79.00 171.00   0.50    0.60    --  121.75  77.00 150.00  184
103  \w     36.00  71.00   0.50    0.60    --  121.75 -91.00 -30.00   70
104  \w    137.00 177.00   0.50    0.60    --  121.75  77.00 -30.00   80
105  \w     80.00 129.00   0.50    0.60    --  121.75  77.00 -30.00   98
106  \w     79.00 118.00   0.50    0.60    --  121.75  77.00  60.00   78
107  \w    129.00 158.00   0.50    0.60    --  121.75  63.00  60.00   58
108  \w     38.00 107.00   0.50    0.60    --  121.75-111.00  30.00  138
109  \w     99.00 125.00   0.50    0.60    --  121.75 -63.00  90.00   52
110  \w     86.00 112.00   0.50    0.60    --  121.75  63.00  60.00   52
111  \w     86.00 153.00   0.50    0.60    --  121.75  63.00 150.00  134
112  \w     44.00  82.00   0.50    0.60    --  121.75 -63.00  90.00   76
113  \w    152.00 177.00   0.50    0.60    --  121.75  77.00 120.00   50
114  \w    140.00 167.00   0.50    0.60    --  121.75  77.00 -90.00   54
115  \w     79.00 129.00   0.50    0.60    --  121.75  77.00 120.00  100
116  \w    131.00 170.00   0.50    0.60    --  121.75  63.00 120.00   78
117  \w     79.00 123.00   0.50    0.60    --  121.75  77.00 -90.00   88
118  \w     87.00 158.00   0.50    0.60    --  121.75  63.00   0.00  142
119  \w     82.00 150.00   0.50    0.60    --  121.75  77.00   0.00  136
120  \w     85.00 156.00   0.50    0.60    --  121.75  63.00-150.00  142
121  \w     73.00 101.00   0.50    0.60    --  121.75 -91.00 -60.00   56
122  \w     41.00  66.00   0.50    0.60    --  121.75 -91.00 -60.00   50
123  \w    123.00 173.00   0.50    0.60    --  121.75  63.00-120.00  100
124  \w     85.00 111.00   0.50    0.60    --  121.75  63.00-120.00   52
125  \w    145.00 176.00   0.50    0.60    --  121.75  77.00-150.00   62
126  \w     33.00 102.00   0.50    0.60    --  121.75 -91.00 -90.00  138
;
_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      -0.1458833000
_diffrn_orient_matrix_UB_12      -0.0533683000
_diffrn_orient_matrix_UB_13      0.0355482000
_diffrn_orient_matrix_UB_21      -0.1044188000
_diffrn_orient_matrix_UB_22      -0.0372949000
_diffrn_orient_matrix_UB_23      -0.0689317000
_diffrn_orient_matrix_UB_31      0.1033979000
_diffrn_orient_matrix_UB_32      -0.1128765000
_diffrn_orient_matrix_UB_33      0.0059712000
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41039
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9958
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.59
_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    0.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.36a (Rigaku Oxford Diffraction, 2021)
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    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             787.088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.3643
_refine_diff_density_min         -0.4007
_refine_diff_density_rms         0.0477
_refine_ls_d_res_high            0.7894
_refine_ls_d_res_low             10.1503
_refine_ls_goodness_of_fit_ref   1.0273
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0273
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.6903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3355
_reflns_number_total             3752
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           41_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250155
_chemical_oxdiff_formula         'C32 H46 O4 N3'
_chemical_oxdiff_usercomment     '100 K, yellow block'
_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 Ternary CH refined with riding coordinates:
 C00H(H00H), C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00a,H00b), C00I(H00c,H00d), C00L(H00e,H00f), C00M(H00g,H00i), C00N(H00j,
 H00l), C00O(H00m,H00n), C00P(H00o,H00p), C00Q(H00q,H00r)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00u), C00D(H00v), C00J(H00w)
2.d X=CH2 refined with riding coordinates:
 N007(H00s,H00t)
;
_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.717