Evaluating structure-property relationship in a new family of mechanically flexible co-crystals
Abeysekera, Amila M.; Averkiev, Boris B.; Sinha, Abhijeet Shekhar; Aakeröy, Christer; Chemical Communications  (2022) –; doi:10.1039/D2CC02047E

data_7130408
_publ_section_title
;
 Evaluating structure-property relationship in a new family of
 mechanically flexible co-crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02047E
_journal_year                    2022
_chemical_formula_moiety         'C7 H7 I N2 O, C7 H5 Cl O2'
_chemical_formula_sum            'C14 H12 Cl I N2 O3'
_chemical_formula_weight         418.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-06-23
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                78.041(2)
_cell_angle_beta                 88.920(2)
_cell_angle_gamma                87.755(2)
_cell_formula_units_Z            2
_cell_length_a                   4.35000(10)
_cell_length_b                   11.5717(2)
_cell_length_c                   15.4381(3)
_cell_measurement_reflns_used    12376
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.6050
_cell_measurement_theta_min      2.8840
_cell_volume                     759.61(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -63.00 -16.00   0.50    1.20    --  -43.30  96.00 -90.00   94
  2  \w     -8.00  26.00   0.50    1.20    --  -43.30  96.00 -90.00   68
  3  \w      4.00  50.00   0.50    1.20    --   43.30 -96.00 160.00   92
  4  \w    -72.00 -47.00   0.50    4.00    --  -90.25  96.00 -90.00   50
  5  \w     73.00 104.00   0.50    4.00    --  111.75 -96.00 160.00   62
  6  \w    142.00 167.00   0.50    4.00    --  111.75  96.00 -90.00   50
  7  \w    -70.00 -28.00   0.50    1.20    --  -43.30  77.00   0.00   84
  8  \w    -23.00  28.00   0.50    1.20    --  -43.30  77.00   0.00  102
  9  \w    -43.00  34.00   0.50    1.20    --  -43.30  38.00 -60.00  154
 10  \w   -116.00 -19.00   0.50    1.20    --  -43.30 -77.00-180.00  194
 11  \w     65.00  97.00   0.50    1.20    --   43.30-125.00-180.00   64
 12  \w   -134.00-108.00   0.50    4.00    --  -90.25 -96.00 160.00   52
 13  \w   -156.00 -83.00   0.50    4.00    --  -90.25 -94.00 -90.00  146
 14  \w    106.00 153.00   0.50    4.00    --  111.75  45.00-120.00   94
 15  \w     38.00  63.00   0.50    4.00    --  111.75 -61.00  60.00   50
 16  \w     89.00 169.00   0.50    4.00    --  111.75  30.00   0.00  160
 17  \w     73.00  98.00   0.50    4.00    --  111.75 -94.00  60.00   50
 18  \w     89.00 147.00   0.50    4.00    --  111.75  30.00 150.00  116
 19  \w     86.00 112.00   0.50    4.00    --  111.75-125.00-120.00   52
 20  \w     73.00 101.00   0.50    4.00    --  111.75  15.00  90.00   56
 21  \w     42.00  68.00   0.50    4.00    --  111.75 -94.00  60.00   52
 22  \w     84.00 111.00   0.50    4.00    --  111.75-125.00   0.00   54
 23  \w     77.00 106.00   0.50    4.00    --  111.75 -94.00   0.00   58
 24  \w     38.00  64.00   0.50    4.00    --  111.75-125.00   0.00   52
 25  \w     59.00  84.00   0.50    4.00    --  111.75-125.00-150.00   50
 26  \w     67.00  97.00   0.50    4.00    --  111.75 -94.00-120.00   60
 27  \w     38.00  64.00   0.50    4.00    --  111.75 -94.00  90.00   52
 28  \w     81.00 106.00   0.50    4.00    --  111.75 -94.00  90.00   50
 29  \w     40.00  91.00   0.50    4.00    --  111.75 -77.00   0.00  102
 30  \w     91.00 158.00   0.50    4.00    --  111.75  45.00-180.00  134
 31  \w     50.00 100.00   0.50    4.00    --  111.75 -94.00  30.00  100
 32  \w     47.00  72.00   0.50    4.00    --  111.75-125.00-120.00   50
 33  \w     80.00 105.00   0.50    4.00    --  111.75 -77.00  90.00   50
 34  \w     89.00 119.00   0.50    4.00    --  111.75  61.00 -90.00   60
 35  \w    140.00 166.00   0.50    4.00    --  111.75  61.00 -90.00   52
 36  \w    147.00 176.00   0.50    4.00    --  111.75  15.00-150.00   58
 37  \w     43.00  93.00   0.50    4.00    --  111.75 -94.00 -90.00  100
 38  \w     83.00 144.00   0.50    4.00    --  111.75  15.00 -90.00  122
 39  \w     39.00  65.00   0.50    4.00    --  111.75 -61.00  30.00   52
 40  \w     49.00  75.00   0.50    4.00    --  111.75 -77.00  90.00   52
 41  \w     38.00  80.00   0.50    4.00    --  111.75 -68.00  84.83   84
 42  \w    144.00 170.00   0.50    4.00    --  111.75  77.00 120.00   52
 43  \w     42.00  67.00   0.50    4.00    --  111.75 -77.00 -60.00   50
 44  \w     70.00 109.00   0.50    4.00    --  111.75-118.00 -49.22   78
 45  \w     52.00  93.00   0.50    4.00    --  111.75 -94.00 -30.00   82
 46  \w     87.00 112.00   0.50    4.00    --  111.75-125.00-150.00   50
 47  \w     80.00 112.00   0.50    4.00    --  111.75-125.00  30.00   64
 48  \w     57.00 106.00   0.50    4.00    --  111.75-125.00 120.00   98
 49  \w     91.00 151.00   0.50    4.00    --  111.75  45.00 150.00  120
 50  \w    127.00 153.00   0.50    4.00    --  111.75  77.00 150.00   52
 51  \w     54.00 104.00   0.50    4.00    --  111.75 -77.00-180.00  100
 52  \w     45.00  77.00   0.50    4.00    --  111.75 -77.00-150.00   64
 53  \w    109.00 176.00   0.50    4.00    --  111.75  15.00  90.00  134
 54  \w     38.00  74.00   0.50    4.00    --  111.75-125.00 -30.00   72
 55  \w     45.00  70.00   0.50    4.00    --  111.75 -61.00 150.00   50
 56  \w     91.00 117.00   0.50    4.00    --  111.75  58.00 135.98   52
 57  \w     91.00 116.00   0.50    4.00    --  111.75  61.00-180.00   50
 58  \w    116.00 141.00   0.50    4.00    --  111.75  77.00  30.00   50
 59  \w    115.00 141.00   0.50    4.00    --  111.75 -80.00-102.39   52
 60  \w     43.00  68.00   0.50    4.00    --  111.75 -94.00   0.00   50
 61  \w    118.00 143.00   0.50    4.00    --  111.75  96.00 -90.00   50
 62  \w     80.00 108.00   0.50    4.00    --  111.75-125.00  90.00   56
 63  \w     84.00 119.00   0.50    4.00    --  111.75  77.00  60.00   70
 64  \w    125.00 151.00   0.50    4.00    --  111.75  77.00  60.00   52
 65  \w     38.00  63.00   0.50    4.00    --  111.75 -61.00 -30.00   50
 66  \w     96.00 122.00   0.50    4.00    --  111.75  67.00-164.73   52
 67  \w    150.00 176.00   0.50    4.00    --  111.75  67.00-164.73   52
 68  \w     49.00  75.00   0.50    4.00    --  111.75 -77.00  30.00   52
 69  \w     62.00  88.00   0.50    4.00    --  111.75 -94.00-180.00   52
 70  \w     81.00 106.00   0.50    4.00    --  111.75 -94.00 120.00   50
 71  \w    143.00 169.00   0.50    4.00    --  111.75  45.00-180.00   52
 72  \w    143.00 169.00   0.50    4.00    --  111.75  45.00-150.00   52
 73  \w    117.00 143.00   0.50    4.00    --  111.75 -83.00 107.03   52
 74  \w     47.00  73.00   0.50    4.00    --  111.75-125.00  90.00   52
 75  \w   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00   0.00  204
 76  \w   -116.00 -20.00   0.50    1.20    --  -43.30 -57.00 -90.00  192
 77  \w   -116.00 -20.00   0.50    1.20    --  -43.30 -57.00  90.00  192
 78  \w   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00  60.00  204
 79  \w   -116.00 -14.00   0.50    1.20    --  -43.30 -77.00 -90.00  204
 80  \w   -120.00 -20.00   0.50    1.20    --  -43.30 -38.00-180.00  200
 81  \w    -34.00  43.00   0.50    1.20    --   43.30 -38.00 150.00  154
 82  \w     14.00 117.00   0.50    1.20    --   43.30  77.00-180.00  206
 83  \w     12.00 123.00   0.50    1.20    --   43.30  19.00  30.00  222
 84  \w     14.00 117.00   0.50    1.20    --   43.30  77.00 -60.00  206
 85  \w     83.00 133.00   0.50    4.00    --  111.75  77.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0837231000
_diffrn_orient_matrix_UB_12      -0.1016123000
_diffrn_orient_matrix_UB_13      0.0783973000
_diffrn_orient_matrix_UB_21      0.0919216000
_diffrn_orient_matrix_UB_22      0.0905336000
_diffrn_orient_matrix_UB_23      0.0544153000
_diffrn_orient_matrix_UB_31      -0.3319252000
_diffrn_orient_matrix_UB_32      0.0046853000
_diffrn_orient_matrix_UB_33      0.0360399000
_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  0.0426
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.860
_diffrn_reflns_theta_min         2.926
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method 'crystallized from ethyl acetate'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.2288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3028
_reflns_number_total             3214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           I-Me_4Cl-BA
_cod_database_code               7130408
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H12N2O3Cl1I1
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C16(H16), C17(H17), C14(H14), C13(H13), C6(H6), C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_olex2_date_sample_data_collection 2021-06-15
_olex2_date_sample_submission    2021-06-15
_olex2_exptl_crystal_mounting_method 'mounted on a MITeGen loop'
_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 1.893
_oxdiff_exptl_absorpt_empirical_full_min 0.569