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_7250154
_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(C2 H4 N2 S2), C12 H24 O6'
_chemical_formula_sum            'C16 H32 N4 O6 S4'
_chemical_formula_weight         504.720
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_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                90
_cell_angle_beta                 104.389(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5145(2)
_cell_length_b                   14.7946(3)
_cell_length_c                   10.0414(2)
_cell_measurement_reflns_used    12824
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3750
_cell_measurement_theta_min      5.4250
_cell_volume                     1225.22(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (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 1.0000
_diffrn_measured_fraction_theta_max 0.9920
_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    -34.00  16.00   0.50    0.05    --    0.00  60.00 123.00  100
  2  \w     81.00 127.00   0.50    0.11    --   66.60  60.00 123.00   92
  3  \w    -12.00  88.00   0.50    0.11    --   66.60 -60.00 -15.00  200
  4  \w     92.00 118.00   0.50    0.11    --  121.75  60.00 123.00   52
  5  \w    113.00 152.00   0.50    0.11    --  121.75 -60.00 -15.00   78
  6  \w     44.00  95.00   0.50    0.11    --  121.75 -60.00 -15.00  102
  7  \w    -84.00 -57.00   0.50    0.05    --    0.00-178.00   0.00   54
  8  \w    -68.00 -29.00   0.50    0.05    --    0.00 -60.00 -15.00   78
  9  \w     21.00  65.00   0.50    0.05    --    0.00  77.00 -60.00   88
 10  \w    -76.00 -39.00   0.50    0.05    --    0.00 178.00-150.00   74
 11  \w     17.00  71.00   0.50    0.05    --    0.00  60.00 123.00  108
 12  \w    -17.00  22.00   0.50    0.05    --    0.00 -60.00 -15.00   78
 13  \w    -94.00 -51.00   0.50    0.05    --    0.00 178.00-180.00   86
 14  \w    -41.00  15.00   0.50    0.05    --    0.00  77.00 -60.00  112
 15  \w    -40.00  -9.00   0.50    0.05    --   18.00 119.00 140.73   62
 16  \w    -10.00  15.00   0.50    0.11    --   38.00 101.00 157.63   50
 17  \w    -12.00  13.00   0.50    0.11    --   42.00 102.00  91.11   50
 18  \w      0.00  33.00   0.50    0.11    --   46.00  89.00  19.91   66
 19  \w      3.00  28.00   0.50    0.11    --   54.00  96.00  48.79   50
 20  \w     10.00  35.00   0.50    0.11    --   58.00  88.00 -27.74   50
 21  \w     14.00  39.00   0.50    0.11    --   62.00  88.00 126.68   50
 22  \w     13.00  42.00   0.50    0.11    --   62.00  91.00 -73.69   58
 23  \w     13.00  38.00   0.50    0.11    --   62.00  90.00  42.36   50
 24  \w     14.00  42.00   0.50    0.11    --   62.00  91.00-137.83   56
 25  \w     14.00  40.00   0.50    0.11    --   62.00  92.00 160.92   52
 26  \w     17.00  42.00   0.50    0.11    --   66.00  90.00  19.02   50
 27  \w     30.00  64.00   0.50    0.11    --   66.60  77.00   0.00   68
 28  \w     71.00 152.00   0.50    0.11    --   66.60  77.00   0.00  162
 29  \w     95.00 146.00   0.50    0.11    --   66.60 125.00-150.00  102
 30  \w     38.00 104.00   0.50    0.11    --   66.60-125.00-150.00  132
 31  \w     34.00 107.00   0.50    0.11    --   66.60-125.00 -60.00  146
 32  \w     41.00 148.00   0.50    0.11    --   70.00  68.00 -93.78  214
 33  \w     31.00 136.00   0.50    0.11    --   70.00  74.00 106.29  210
 34  \w     32.00  58.00   0.50    0.11    --   74.00  75.00 -21.30   52
 35  \w    119.00 148.00   0.50    0.11    --   74.00  74.00  43.15   58
 36  \w     39.00  81.00   0.50    0.11    --   74.00  74.00  43.15   84
 37  \w     76.00 159.00   0.50    0.11    --   74.00  75.00 -21.30  166
 38  \w     41.00  99.00   0.50    0.11    --   78.00  69.00 178.92  116
 39  \w     37.00 107.00   0.50    0.11    --   78.00  75.00-145.91  140
 40  \w    114.00 140.00   0.50    0.11    --   78.00  68.00 152.59   52
 41  \w     40.00  78.00   0.50    0.11    --   78.00  68.00 152.59   76
 42  \w    119.00 145.00   0.50    0.11    --   78.00  75.00-145.91   52
 43  \w     39.00  74.00   0.50    0.11    --   82.00  76.00 -15.34   70
 44  \w     39.00  99.00   0.50    0.11    --   82.00  76.00  69.85  120
 45  \w     45.00  71.00   0.50    0.11    --   86.00  74.00 -99.05   52
 46  \w     45.00  80.00   0.50    0.11    --   86.00  75.00 144.35   70
 47  \w    145.00 170.00   0.50    0.11    --   86.00  74.00 -99.05   50
 48  \w     45.00  75.00   0.50    0.11    --   86.00  76.00  85.84   60
 49  \w     45.00  72.00   0.50    0.11    --   86.00  72.00-128.95   54
 50  \w    103.00 173.00   0.50    0.11    --   90.00  76.00 103.26  140
 51  \w     47.00  75.00   0.50    0.11    --   90.00  76.00 103.26   56
 52  \w     50.00  77.00   0.50    0.11    --   90.00  71.00  13.99   54
 53  \w    147.00 173.00   0.50    0.11    --   90.00  74.00 -75.22   52
 54  \w    134.00 160.00   0.50    0.11    --   90.00  71.00  13.99   52
 55  \w     48.00  74.00   0.50    0.11    --   90.00  74.00 -75.22   52
 56  \w     56.00 104.00   0.50    0.11    --   94.00  69.00 -49.16   96
 57  \w     57.00 130.00   0.50    0.11    --   94.00  65.00  76.23  146
 58  \w     59.00  84.00   0.50    0.11    --   94.00  63.00-175.25   50
 59  \w     55.00 125.00   0.50    0.11    --   94.00  70.00-149.60  140
 60  \w     58.00  86.00   0.50    0.11    --   98.00  71.00  23.70   56
 61  \w    125.00 151.00   0.50    0.11    --   98.00  72.00-121.45   52
 62  \w     58.00 118.00   0.50    0.11    --   98.00  72.00-121.45  120
 63  \w    146.00 171.00   0.50    0.11    --   98.00  62.00 142.14   50
 64  \w     62.00 119.00   0.50    0.11    --   98.00  62.00 142.14  114
 65  \w     62.00 167.00   0.50    0.11    --  102.00  75.00  83.73  210
 66  \w     60.00  95.00   0.50    0.11    --  102.00  74.00  -8.78   70
 67  \w     63.00  89.00   0.50    0.11    --  102.00  70.00 -77.66   52
 68  \w     65.00 164.00   0.50    0.11    --  106.00  72.00  41.36  198
 69  \w     73.00 103.00   0.50    0.11    --  114.00  75.00-119.69   60
 70  \w    134.00 160.00   0.50    0.11    --  114.00  77.00 161.00   52
 71  \w     71.00 117.00   0.50    0.11    --  114.00  77.00 161.00   92
 72  \w     78.00 126.00   0.50    0.11    --  118.00  70.00 -36.87   96
 73  \w    132.00 178.00   0.50    0.11    --  118.00  70.00 -36.87   92
 74  \w     88.00 161.00   0.50    0.11    --  121.75  77.00-120.00  146
 75  \w     83.00 108.00   0.50    0.11    --  121.75-111.00 120.00   50
 76  \w     41.00 105.00   0.50    0.11    --  121.75-111.00 150.00  128
 77  \w     38.00  76.00   0.50    0.11    --  121.75-111.00 -90.00   76
 78  \w     39.00  78.00   0.50    0.11    --  121.75-111.00 120.00   78
 79  \w    144.00 170.00   0.50    0.11    --  121.75  77.00   0.00   52
 80  \w     81.00 129.00   0.50    0.11    --  121.75  77.00   0.00   96
 81  \w     69.00  96.00   0.50    0.11    --  121.75-111.00-180.00   54
 82  \w     81.00 159.00   0.50    0.11    --  121.75  72.00-161.00  156
 83  \w    120.00 150.00   0.50    0.11    --  121.75  50.00 150.00   60
 84  \w     43.00  99.00   0.50    0.11    --  121.75 -91.00 -30.00  112
 85  \w     38.00  65.00   0.50    0.11    --  121.75-111.00-180.00   54
 86  \w     88.00 164.00   0.50    0.11    --  121.75  63.00 150.00  152
 87  \w     87.00 161.00   0.50    0.11    --  121.75  63.00 -60.00  148
 88  \w     85.00 161.00   0.50    0.11    --  121.75  63.00 -90.00  152
 89  \w     75.00 101.00   0.50    0.11    --  121.75 -91.00-180.00   52
 90  \w     36.00  64.00   0.50    0.11    --  121.75 -91.00-180.00   56
 91  \w     90.00 119.00   0.50    0.11    --  121.75  63.00  60.00   58
 92  \w     77.00 142.00   0.50    0.11    --  121.75 178.00   0.00  130
 93  \w     79.00 168.00   0.50    0.11    --  121.75  77.00-150.00  178
 94  \w    135.00 175.00   0.50    0.11    --  121.75  77.00 120.00   80
 95  \w    114.00 160.00   0.50    0.11    --  121.75  77.00  90.00   92
 96  \w     80.00 113.00   0.50    0.11    --  121.75  77.00 120.00   66
 97  \w     83.00 153.00   0.50    0.11    --  121.75  77.00 -30.00  140
 98  \w     83.00 109.00   0.50    0.11    --  121.75  77.00  90.00   52
 99  \w    116.00 141.00   0.50    0.11    --  121.75  77.00 -60.00   50
100  \w     80.00 106.00   0.50    0.11    --  121.75  77.00 -60.00   52
101  \w     44.00 107.00   0.50    0.11    --  121.75-111.00 -30.00  126
102  \w    104.00 171.00   0.50    0.11    --  121.75 111.00 150.00  134
103  \w    101.00 140.00   0.50    0.11    --  121.75  63.00   0.00   78
104  \w     67.00 107.00   0.50    0.11    --  121.75-111.00  90.00   80
105  \w    153.00 178.00   0.50    0.11    --  121.75  77.00-180.00   50
106  \w     80.00 112.00   0.50    0.11    --  121.75  77.00 -90.00   64
107  \w     82.00 130.00   0.50    0.11    --  121.75  77.00-180.00   96
108  \w     52.00 108.00   0.50    0.11    --  121.75-111.00-120.00  112
109  \w     71.00 106.00   0.50    0.11    --  121.75-111.00 -60.00   70
110  \w    125.00 176.00   0.50    0.11    --  121.75  50.00 120.00  102
111  \w     82.00 118.00   0.50    0.11    --  121.75  50.00 120.00   72
112  \w     74.00 100.00   0.50    0.11    --  121.75 -91.00   0.00   52
113  \w     83.00 178.00   0.50    0.11    --  121.75  77.00  60.00  190
114  \w     84.00 170.00   0.50    0.11    --  121.75  77.00  30.00  172
115  \w     47.00  72.00   0.50    0.11    --  121.75 -91.00   0.00   50
116  \w     65.00 138.00   0.50    0.11    --  121.75 178.00 -60.00  146
;
_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      0.1558450000
_diffrn_orient_matrix_UB_12      -0.0435483000
_diffrn_orient_matrix_UB_13      0.0880896000
_diffrn_orient_matrix_UB_21      0.0122121000
_diffrn_orient_matrix_UB_22      -0.0597747000
_diffrn_orient_matrix_UB_23      -0.1225736000
_diffrn_orient_matrix_UB_31      0.1022681000
_diffrn_orient_matrix_UB_32      0.0733625000
_diffrn_orient_matrix_UB_33      -0.0477500000
_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  0.0618
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9920
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25884
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9920
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         78.00
_diffrn_reflns_theta_min         5.44
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (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    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             540.261
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.5527
_refine_diff_density_min         -0.2317
_refine_diff_density_rms         0.0589
_refine_ls_d_res_high            0.7881
_refine_ls_d_res_low             8.1273
_refine_ls_goodness_of_fit_ref   1.0475
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0475
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.4404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -6
_reflns_number_gt                2442
_reflns_number_total             2606
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ce00025d2.cif
_cod_data_source_block           50_C1_red1_abs1
_cod_depositor_comments
'Adding full bibliography for 7250152--7250159.cif.'
_cod_database_code               7250154
_chemical_oxdiff_formula         'C20 H40 S2 N2'
_chemical_oxdiff_usercomment     '100 K, yellow block'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C22(H22a,H22b), C23(H23a,H23b), C24(H24a,H24b), C25(H25a,
 H25b), C26(H26a,H26b)
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 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.564