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_7250152
_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         'C2 H4 N2 S2, C12 H24 O6, 2(H2 O)'
_chemical_formula_sum            'C14 H32 N2 O8 S2'
_chemical_formula_weight         420.551
_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             2024-03-11
_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                74.404(3)
_cell_angle_beta                 72.510(3)
_cell_angle_gamma                75.828(3)
_cell_formula_units_Z            1
_cell_length_a                   7.3962(3)
_cell_length_b                   7.7483(3)
_cell_length_c                   10.1053(3)
_cell_measurement_reflns_used    7895
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3950
_cell_measurement_theta_min      4.6880
_cell_volume                     523.46(4)
_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 0.9989
_diffrn_measured_fraction_theta_max 0.9811
_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     24.00  50.00   0.50    1.00    --    0.00  70.00  62.00   52
  2  \w    -95.00 -43.00   0.50    1.00    --    0.00-178.00-120.00  104
  3  \w    -18.00  36.00   0.50    1.00    --    0.00 -70.00 -69.00  108
  4  \w    -66.00 -40.00   0.50    1.00    --    0.00 -70.00 -69.00   52
  5  \w    -80.00 -14.00   0.50    1.00    --    0.00 -77.00 -90.00  132
  6  \w    -83.00 -41.00   0.50    1.00    --    0.00-178.00  30.00   84
  7  \w    -37.00  11.00   0.50    1.00    --    0.00  70.00  62.00   96
  8  \w    -33.00  -6.00   0.50    1.00    --   22.00 111.00 -89.91   54
  9  \w    -22.00   3.00   0.50    1.00    --   34.00 104.00-104.43   50
 10  \w    -17.00   8.00   0.50    1.00    --   38.00 102.00 169.92   50
 11  \w     11.00  37.00   0.50    1.00    --   42.00  81.00 -33.50   52
 12  \w      8.00  33.00   0.50    1.00    --   58.00  93.00  76.40   50
 13  \w      8.00  33.00   0.50    1.00    --   58.00  93.00 -83.97   50
 14  \w     17.00  42.00   0.50    1.00    --   62.00  85.00 -62.28   50
 15  \w     15.00  42.00   0.50    1.00    --   62.00  89.00  -6.17   54
 16  \w     14.00  39.00   0.50    1.00    --   62.00  88.00  59.43   50
 17  \w     12.00  42.00   0.50    1.00    --   62.00  92.00-170.95   60
 18  \w     15.00  41.00   0.50    1.00    --   62.00  89.00 150.58   52
 19  \w    -13.00  69.00   0.50    1.00    --   66.57 -70.00 -69.00  164
 20  \w     63.00 115.00   0.50    1.00    --   66.57  70.00  62.00  104
 21  \w     75.00 108.00   0.50    1.00    --   66.57  77.00-180.00   66
 22  \w    -13.00 108.00   0.50    1.00    --   66.57 -45.00-150.00  242
 23  \w     72.00 104.00   0.50    1.00    --   66.57 -94.00  60.00   64
 24  \w     52.00 100.00   0.50    1.00    --   66.57 -61.00 120.00   96
 25  \w     26.00  59.00   0.50    1.00    --   66.57  77.00 120.00   66
 26  \w     68.00  94.00   0.50    1.00    --   66.57 -61.00   0.00   52
 27  \w     53.00 106.00   0.50    1.00    --   66.57 -94.00 -60.00  106
 28  \w     25.00  51.00   0.50    1.00    --   66.57  77.00-120.00   52
 29  \w     35.00  73.00   0.50    1.00    --   66.57  77.00  90.00   76
 30  \w      4.00  45.00   0.50    1.00    --   66.57 -61.00 120.00   82
 31  \w     32.00  57.00   0.50    1.00    --   66.57  77.00-180.00   50
 32  \w    -11.00  66.00   0.50    1.00    --   66.57 -61.00   0.00  154
 33  \w     43.00 108.00   0.50    1.00    --   70.00  77.00 -22.72  130
 34  \w     31.00 103.00   0.50    1.00    --   74.00  77.00 -85.96  144
 35  \w     40.00  92.00   0.50    1.00    --   78.00  67.00-106.68  104
 36  \w     36.00  76.00   0.50    1.00    --   78.00  76.00 -40.47   80
 37  \w     74.00 100.00   0.50    1.00    --   78.00  76.00 140.63   52
 38  \w     37.00  63.00   0.50    1.00    --   78.00  76.00 140.63   52
 39  \w     99.00 156.00   0.50    1.00    --   78.00  67.00-106.68  114
 40  \w     42.00  71.00   0.50    1.00    --   82.00  76.00  51.82   58
 41  \w     42.00  67.00   0.50    1.00    --   82.00  77.00  -5.69   50
 42  \w     73.00  99.00   0.50    1.00    --   82.00  77.00  -5.69   52
 43  \w     47.00  73.00   0.50    1.00    --   86.00  74.00  18.91   52
 44  \w     46.00  76.00   0.50    1.00    --   86.00  75.00 138.02   60
 45  \w     47.00  72.00   0.50    1.00    --   86.00  75.00-159.87   50
 46  \w     47.00 105.00   0.50    1.00    --   90.00  77.00 100.15  116
 47  \w    119.00 173.00   0.50    1.00    --   94.00  65.00 -35.96  108
 48  \w     57.00 102.00   0.50    1.00    --   94.00  65.00 -35.96   90
 49  \w     51.00  77.00   0.50    1.00    --   94.00  77.00-135.06   52
 50  \w     52.00  81.00   0.50    1.00    --   94.00  76.00 167.65   58
 51  \w     84.00 109.00   0.50    1.00    --   94.00  77.00-135.06   50
 52  \w     73.00 130.00   0.50    1.00    --   98.00  64.00-147.71  114
 53  \w     57.00  97.00   0.50    1.00    --   98.00  72.00  71.01   80
 54  \w    133.00 176.00   0.50    1.00    --   98.00  64.00-147.71   86
 55  \w     60.00  85.00   0.50    1.00    --  102.00  75.00 139.13   50
 56  \w    110.00 167.00   0.50    1.00    --  102.00  67.00 133.61  114
 57  \w     66.00  91.00   0.50    1.00    --  102.00  67.00 133.61   50
 58  \w     60.00 101.00   0.50    1.00    --  102.00  74.00-100.96   82
 59  \w     60.00  85.00   0.50    1.00    --  102.00  76.00   3.71   50
 60  \w    112.00 137.00   0.50    1.00    --  102.00  67.00  48.59   50
 61  \w     65.00  91.00   0.50    1.00    --  102.00  67.00  48.59   52
 62  \w     61.00  99.00   0.50    1.00    --  102.00  76.00  21.53   76
 63  \w     49.00 107.00   0.50    1.00    --  121.75 -70.00 -69.00  116
 64  \w    124.00 150.00   0.50    1.00    --  121.75 -70.00 -69.00   52
 65  \w    134.00 170.00   0.50    1.00    --  121.75  70.00  62.00   72
 66  \w     87.00 128.00   0.50    1.00    --  121.75  70.00  62.00   82
 67  \w     68.00 102.00   0.50    1.00    --  121.75 -91.00 -90.00   68
 68  \w     86.00 115.00   0.50    1.00    --  121.75  50.00  60.00   58
 69  \w     52.00  89.00   0.50    1.00    --  121.75 -91.00-120.00   74
 70  \w    131.00 158.00   0.50    1.00    --  121.75  63.00 150.00   54
 71  \w     85.00 117.00   0.50    1.00    --  121.75  63.00 150.00   64
 72  \w     68.00 107.00   0.50    1.00    --  121.75-111.00  53.21   78
 73  \w    119.00 174.00   0.50    1.00    --  121.75 -37.00  90.00  110
 74  \w     35.00 109.00   0.50    1.00    --  121.75 -37.00  90.00  148
 75  \w    132.00 157.00   0.50    1.00    --  121.75 -50.00-120.00   50
 76  \w     95.00 123.00   0.50    1.00    --  121.75 -50.00-120.00   56
 77  \w     47.00  81.00   0.50    1.00    --  121.75 -50.00-120.00   68
 78  \w     90.00 135.00   0.50    1.00    --  121.75  50.00 120.00   90
 79  \w     88.00 131.00   0.50    1.00    --  121.75  50.00 -30.00   86
 80  \w    128.00 176.00   0.50    1.00    --  121.75  63.00-120.00   96
 81  \w    124.00 175.00   0.50    1.00    --  121.75  61.00 -59.54  102
 82  \w    142.00 168.00   0.50    1.00    --  121.75  50.00 -90.00   52
 83  \w     92.00 121.00   0.50    1.00    --  121.75  63.00-150.00   58
 84  \w     85.00 151.00   0.50    1.00    --  121.75 -50.00 -30.00  132
 85  \w     86.00 117.00   0.50    1.00    --  121.75  61.00 -59.54   62
 86  \w     41.00  78.00   0.50    1.00    --  121.75 -50.00 -30.00   74
 87  \w    128.00 158.00   0.50    1.00    --  121.75 -63.00 120.00   60
 88  \w     87.00 140.00   0.50    1.00    --  121.75  50.00 -90.00  106
 89  \w     98.00 124.00   0.50    1.00    --  121.75 -63.00 120.00   52
 90  \w    153.00 178.00   0.50    1.00    --  121.75  63.00-180.00   50
 91  \w     88.00 118.00   0.50    1.00    --  121.75  63.00-180.00   60
 92  \w    126.00 175.00   0.50    1.00    --  121.75  63.00 -30.00   98
 93  \w     89.00 116.00   0.50    1.00    --  121.75  63.00 -30.00   54
 94  \w    139.00 177.00   0.50    1.00    --  121.75  50.00-180.00   76
 95  \w     83.00 118.00   0.50    1.00    --  121.75  50.00-180.00   70
 96  \w    134.00 172.00   0.50    1.00    --  121.75  50.00-150.00   76
 97  \w     94.00 120.00   0.50    1.00    --  121.75  63.00 120.00   52
 98  \w     61.00 107.00   0.50    1.00    --  121.75-103.00-149.40   92
 99  \w    130.00 178.00   0.50    1.00    --  121.75  50.00  30.00   96
100  \w     88.00 120.00   0.50    1.00    --  121.75  63.00-120.00   64
101  \w     89.00 120.00   0.50    1.00    --  121.75  50.00-150.00   62
102  \w     52.00  93.00   0.50    1.00    --  121.75 -91.00 120.00   82
103  \w     83.00 125.00   0.50    1.00    --  121.75  50.00  30.00   84
104  \w    141.00 170.00   0.50    1.00    --  121.75  50.00 120.00   58
105  \w     57.00 105.00   0.50    1.00    --  121.75 -91.00 150.00   96
106  \w    125.00 169.00   0.50    1.00    --  121.75  63.00  90.00   88
107  \w     86.00 112.00   0.50    1.00    --  121.75  63.00  90.00   52
108  \w     59.00 102.00   0.50    1.00    --  121.75 -91.00  90.00   86
109  \w     78.00 149.00   0.50    1.00    --  121.75  37.00  30.00  142
110  \w     76.00 102.00   0.50    1.00    --  121.75 -91.00  30.00   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      0.0348330000
_diffrn_orient_matrix_UB_12      -0.1527125000
_diffrn_orient_matrix_UB_13      0.1282693000
_diffrn_orient_matrix_UB_21      -0.1642358000
_diffrn_orient_matrix_UB_22      -0.0846065000
_diffrn_orient_matrix_UB_23      -0.0067188000
_diffrn_orient_matrix_UB_31      0.1451805000
_diffrn_orient_matrix_UB_32      -0.1163453000
_diffrn_orient_matrix_UB_33      -0.1012087000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9811
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9294
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9811
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.63
_diffrn_reflns_theta_min         4.69
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_T_max  0.291
_exptl_absorpt_correction_T_min  0.074
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             227.443
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.3689
_refine_diff_density_min         -0.1650
_refine_diff_density_rms         0.0455
_refine_ls_d_res_high            0.7893
_refine_ls_d_res_low             9.4208
_refine_ls_goodness_of_fit_ref   1.0517
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0517
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.0690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2136
_reflns_number_total             2186
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           49_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250152
_chemical_oxdiff_formula         'C26 H40 S2 N2 I2  F4'
_chemical_oxdiff_usercomment     '100K '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31a,H31b), C32(H32a,H32b), C33(H33a,H33b), C34(H34a,H34b), C35(H35a,
 H35b), C36(H36a,H36b)
2.b X=CH2 refined with riding coordinates:
 N11(H11a,H11b)
;
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.621