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_7130412
_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         'C8 H9 I N2 O, C9 H10 O2'
_chemical_formula_sum            'C17 H19 I N2 O3'
_chemical_formula_weight         426.24
_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     dual
_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                97.439(2)
_cell_angle_beta                 94.401(3)
_cell_angle_gamma                93.065(3)
_cell_formula_units_Z            2
_cell_length_a                   4.5288(2)
_cell_length_b                   12.8682(4)
_cell_length_c                   15.2840(4)
_cell_measurement_reflns_used    15005
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.7210
_cell_measurement_theta_min      2.9380
_cell_volume                     878.80(5)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.982
_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    -79.00  -5.00   0.50    1.80    --  -43.05 112.00  19.00  148
  2  \w     25.00  86.00   0.50    1.80    --   43.05-112.00 -72.00  122
  3  \w   -128.00-100.00   0.50    7.40    --  -90.25-112.00 -72.00   56
  4  \w    -70.00 -43.00   0.50    7.40    --  -90.25 112.00  19.00   54
  5  \w     82.00 107.00   0.50    7.40    --  111.75-112.00 -72.00   50
  6  \w    108.00 164.00   0.50    7.40    --  111.75 112.00  19.00  112
  7  \w    -63.00  28.00   0.50    1.80    --  -43.05  57.00 -60.00  182
  8  \w    -52.00 -14.00   0.50    1.80    --  -43.05 -77.00-150.00   76
  9  \w    -51.00 -20.00   0.50    1.80    --  -43.05 -38.00-150.00   62
 10  \w    -62.00 -14.00   0.50    1.80    --  -43.05 -77.00  90.00   96
 11  \w   -120.00 -73.00   0.50    1.80    --  -43.05 -38.00   0.00   94
 12  \w    -68.00 -20.00   0.50    1.80    --  -43.05 -38.00   0.00   96
 13  \w    -66.00 -20.00   0.50    1.80    --  -43.05 -57.00 -90.00   92
 14  \w     83.00 114.00   0.50    1.80    --   43.05  57.00-120.00   62
 15  \w     38.00  95.00   0.50    1.80    --   43.05-125.00  30.00  114
 16  \w     25.00  62.00   0.50    1.80    --   43.05  38.00  60.00   74
 17  \w     29.00  59.00   0.50    1.80    --   43.05  57.00-120.00   60
 18  \w     82.00 110.00   0.50    1.80    --   43.05  57.00  90.00   56
 19  \w     23.00  49.00   0.50    1.80    --   43.05  57.00  90.00   52
 20  \w     15.00  43.00   0.50    1.80    --   46.00  87.00 -53.97   56
 21  \w     14.00  39.00   0.50    1.80    --   46.00  85.00-102.22   50
 22  \w     17.00  42.00   0.50    1.80    --   50.00  87.00  39.44   50
 23  \w     16.00  43.00   0.50    1.80    --   50.00  90.00 129.80   54
 24  \w     17.00  42.00   0.50    1.80    --   50.00  87.00  82.02   50
 25  \w     17.00  42.00   0.50    1.80    --   50.00  86.00-140.93   50
 26  \w   -120.00 -93.00   0.50    1.80    --  -54.00 -76.00  57.11   54
 27  \w    -66.00 -25.00   0.50    1.80    --  -54.00 -76.00  57.11   82
 28  \w    -90.00 -34.00   0.50    1.80    --  -58.00 -67.00-155.28  112
 29  \w     32.00  86.00   0.50    1.80    --   58.00  76.00  -6.61  108
 30  \w    -67.00 -39.00   0.50    1.80    --  -62.00 -63.00-141.26   56
 31  \w     34.00  61.00   0.50    1.80    --   62.00  75.00 148.80   54
 32  \w    100.00 125.00   0.50    1.80    --   62.00  75.00 148.80   50
 33  \w    -65.00 -37.00   0.50    1.80    --  -66.00 -76.00 -74.21   56
 34  \w    -95.00 -46.00   0.50    1.80    --  -66.00 -55.00 122.55   98
 35  \w    -75.00 -45.00   0.50    1.80    --  -66.00 -60.00 145.26   60
 36  \w    -74.00 -46.00   0.50    1.80    --  -66.00 -59.00-126.80   56
 37  \w   -111.00 -83.00   0.50    1.80    --  -66.00 -65.00-177.16   56
 38  \w    -78.00 -43.00   0.50    1.80    --  -66.00 -65.00-177.16   70
 39  \w    -73.00 -45.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 40  \w    -67.00 -42.00   0.50    7.40    --  -70.00 -75.00-138.16   50
 41  \w    -74.00 -47.00   0.50    7.40    --  -70.00 -63.00 162.05   54
 42  \w   -138.00-110.00   0.50    7.40    --  -70.00 -67.00  86.78   56
 43  \w    -94.00 -62.00   0.50    7.40    --  -74.00 -54.00  58.54   64
 44  \w    -74.00 -46.00   0.50    7.40    --  -74.00 -74.00 -75.85   56
 45  \w    -79.00 -51.00   0.50    7.40    --  -74.00 -62.00 -62.50   56
 46  \w    -78.00 -50.00   0.50    7.40    --  -74.00 -61.00-141.34   56
 47  \w    -72.00 -47.00   0.50    7.40    --  -74.00 -73.00 113.57   50
 48  \w   -112.00 -84.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 49  \w    -81.00 -53.00   0.50    7.40    --  -74.00 -58.00 -52.85   56
 50  \w    -78.00 -51.00   0.50    7.40    --  -78.00 -72.00-158.59   54
 51  \w    -79.00 -54.00   0.50    7.40    --  -82.00 -74.00  43.24   50
 52  \w   -148.00-119.00   0.50    7.40    --  -82.00 -74.00  43.24   58
 53  \w    -82.00 -54.00   0.50    7.40    --  -82.00 -74.00 -75.68   56
 54  \w    -82.00 -54.00   0.50    7.40    --  -82.00 -75.00 131.65   56
 55  \w    -81.00 -53.00   0.50    7.40    --  -82.00 -76.00   5.80   56
 56  \w    -80.00 -55.00   0.50    7.40    --  -82.00 -71.00  21.41   50
 57  \w   -160.00-133.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 58  \w    -87.00 -60.00   0.50    7.40    --  -86.00 -73.00   3.05   54
 59  \w    -90.00 -63.00   0.50    7.40    --  -90.00 -71.00 161.19   54
 60  \w    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 61  \w    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00-180.00   56
 62  \w   -159.00-131.00   0.50    7.40    --  -90.25 -77.00 -30.00   56
 63  \w    -90.00 -65.00   0.50    7.40    --  -90.25 -68.00 -54.36   50
 64  \w    -87.00 -62.00   0.50    7.40    --  -90.25 -75.00  66.30   50
 65  \w    -89.00 -61.00   0.50    7.40    --  -90.25 -77.00  30.00   56
 66  \w   -114.00 -63.00   0.50    7.40    --  -90.25 -77.00 120.00  102
 67  \w    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-174.33   54
 68  \w    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00 -60.00   54
 69  \w    -89.00 -62.00   0.50    7.40    --  -90.25 -74.00 127.72   54
 70  \w    -88.00 -61.00   0.50    7.40    --  -90.25 -77.00-120.00   54
 71  \w    -91.00 -64.00   0.50    7.40    --  -90.25 -71.00  42.63   54
 72  \w    -86.00 -61.00   0.50    7.40    --  -90.25 -77.00   0.00   50
 73  \w    -91.00 -63.00   0.50    7.40    --  -90.25 -72.00  -0.09   56
 74  \w    -87.00 -62.00   0.50    7.40    --  -90.25 -76.00 -85.25   50
 75  \w   -147.00-121.00   0.50    7.40    --  -90.25 -72.00  -0.09   52
 76  \w    -90.00 -63.00   0.50    7.40    --  -90.25 -73.00-143.56   54
 77  \w     35.00 108.00   0.50    7.40    --  110.00-112.00  28.88  146
 78  \w    139.00 178.00   0.50    7.40    --  111.75  77.00 -60.00   78
 79  \w     84.00 125.00   0.50    7.40    --  111.75  77.00 -60.00   82
 80  \w    115.00 159.00   0.50    7.40    --  111.75 125.00  90.00   88
 81  \w    120.00 159.00   0.50    7.40    --  111.75 125.00 -60.00   78
 82  \w     41.00  84.00   0.50    7.40    --  111.75-125.00 -30.00   86
 83  \w     83.00 115.00   0.50    7.40    --  111.75  77.00-150.00   64
 84  \w     85.00 175.00   0.50    7.40    --  111.75  77.00   0.00  180
 85  \w     73.00 100.00   0.50    7.40    --  111.75 -94.00-150.00   54
 86  \w     88.00 173.00   0.50    7.40    --  111.75  61.00 120.00  170
 87  \w     41.00  68.00   0.50    7.40    --  111.75 -94.00-150.00   54
 88  \w     42.00  71.00   0.50    7.40    --  111.75 -61.00  30.00   58
 89  \w     88.00 173.00   0.50    7.40    --  111.75  61.00-120.00  170
 90  \w     89.00 147.00   0.50    7.40    --  111.75  61.00 -90.00  116
 91  \w     78.00 105.00   0.50    7.40    --  111.75 -77.00 150.00   54
 92  \w     93.00 125.00   0.50    7.40    --  111.75  45.00  60.00   64
 93  \w     42.00 105.00   0.50    7.40    --  111.75-125.00   0.00  126
 94  \w     71.00 104.00   0.50    7.40    --  111.75 -77.00-120.00   66
 95  \w     90.00 167.00   0.50    7.40    --  111.75  61.00 -60.00  154
 96  \w     44.00  78.00   0.50    7.40    --  111.75-114.00  41.78   68
 97  \w    121.00 174.00   0.50    7.40    --  111.75  77.00  30.00  106
 98  \w     88.00 116.00   0.50    7.40    --  111.75  77.00  30.00   56
 99  \w     55.00 106.00   0.50    7.40    --  111.75 -94.00  60.00  102
100  \w    130.00 178.00   0.50    7.40    --  111.75  77.00 -90.00   96
101  \w     85.00 115.00   0.50    7.40    --  111.75  77.00 -90.00   60
102  \w     80.00 106.00   0.50    7.40    --  111.75 -94.00 -60.00   52
103  \w    130.00 162.00   0.50    7.40    --  111.75  61.00 -30.00   64
104  \w     43.00  69.00   0.50    7.40    --  111.75 -61.00 -90.00   52
105  \w    131.00 158.00   0.50    7.40    --  111.75  15.00   0.00   54
106  \w     40.00  67.00   0.50    7.40    --  111.75 -94.00 -60.00   54
107  \w     38.00  63.00   0.50    7.40    --  111.75 -61.00 -30.00   50
108  \w     44.00  69.00   0.50    7.40    --  111.75 -61.00   0.00   50
109  \w     87.00 112.00   0.50    7.40    --  111.75  15.00   0.00   50
110  \w     89.00 175.00   0.50    7.40    --  111.75  61.00-150.00  172
111  \w     39.00  99.00   0.50    7.40    --  111.75 -77.00  90.00  120
112  \w     38.00  75.00   0.50    7.40    --  111.75 -77.00 150.00   74
113  \w    129.00 157.00   0.50    7.40    --  111.75  15.00-180.00   56
114  \w     85.00 135.00   0.50    7.40    --  111.75  77.00-120.00  100
115  \w     90.00 123.00   0.50    7.40    --  111.75  61.00 -30.00   66
116  \w     62.00 108.00   0.50    7.40    --  111.75  15.00-180.00   92
117  \w    121.00 148.00   0.50    7.40    --  111.75-177.00 178.98   54
118  \w     66.00 105.00   0.50    7.40    --  111.75-177.00 178.98   78
119  \w    153.00 178.00   0.50    7.40    --  111.75  61.00-180.00   50
120  \w     91.00 139.00   0.50    7.40    --  111.75  61.00 150.00   96
121  \w     65.00 106.00   0.50    7.40    --  111.75 -94.00  90.00   82
122  \w     43.00  68.00   0.50    7.40    --  111.75 -61.00-120.00   50
123  \w     83.00 157.00   0.50    7.40    --  111.75  77.00  60.00  148
124  \w     92.00 133.00   0.50    7.40    --  111.75  61.00-180.00   82
125  \w     85.00 174.00   0.50    7.40    --  111.75  71.00  81.25  178
126  \w    140.00 177.00   0.50    7.40    --  111.75  77.00 -30.00   74
127  \w     85.00 112.00   0.50    7.40    --  111.75  77.00 -30.00   54
128  \w    124.00 170.00   0.50    7.40    --  111.75  45.00-180.00   92
129  \w     92.00 136.00   0.50    7.40    --  111.75  45.00   0.00   88
130  \w     41.00 100.00   0.50    7.40    --  111.75 -94.00-120.00  118
131  \w    117.00 175.00   0.50    7.40    --  111.75  77.00 150.00  116
132  \w    139.00 166.00   0.50    7.40    --  111.75  77.00-180.00   54
133  \w     88.00 134.00   0.50    7.40    --  111.75  77.00-180.00   92
134  \w     83.00 113.00   0.50    7.40    --  111.75  77.00 150.00   60
135  \w    129.00 156.00   0.50    7.40    --  111.75  77.00  90.00   54
136  \w     98.00 126.00   0.50    7.40    --  111.75  45.00 150.00   56
137  \w     86.00 113.00   0.50    7.40    --  111.75  77.00  90.00   54
138  \w     89.00 155.00   0.50    7.40    --  111.75  61.00  60.00  132
139  \w     82.00 112.00   0.50    7.40    --  111.75-125.00 -90.00   60
140  \w    118.00 148.00   0.50    7.40    --  111.75 125.00-120.00   60
141  \w     79.00 111.00   0.50    7.40    --  111.75-125.00-150.00   64
142  \w    142.00 168.00   0.50    7.40    --  111.75  61.00  30.00   52
143  \w     61.00 102.00   0.50    7.40    --  111.75 -94.00 120.00   82
144  \w     72.00  97.00   0.50    7.40    --  111.75 -77.00 -60.00   50
145  \w     96.00 160.00   0.50    7.40    --  111.75  61.00   0.00  128
146  \w     88.00 115.00   0.50    7.40    --  111.75  61.00  30.00   54
147  \w     41.00  66.00   0.50    7.40    --  111.75-125.00 -90.00   50
148  \w     42.00  95.00   0.50    7.40    --  111.75 -77.00  30.00  106
149  \w     38.00  63.00   0.50    7.40    --  111.75 -61.00 120.00   50
150  \w    126.00 172.00   0.50    7.40    --  111.75  77.00-150.00   92
;
_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      0.0920977000
_diffrn_orient_matrix_UB_12      0.0278304000
_diffrn_orient_matrix_UB_13      -0.0895335000
_diffrn_orient_matrix_UB_21      0.1146551000
_diffrn_orient_matrix_UB_22      0.1104642000
_diffrn_orient_matrix_UB_23      0.0447875000
_diffrn_orient_matrix_UB_31      0.3086289000
_diffrn_orient_matrix_UB_32      -0.0407468000
_diffrn_orient_matrix_UB_33      0.0196271000
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.029
_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    14.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66677
_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    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.954
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+1.3675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           I-Et_35M-BA
_cod_database_code               7130412
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H19IN2O3
_shelx_estimated_absorpt_t_max   0.483
_shelx_estimated_absorpt_t_min   0.213
_reflns_odcompleteness_completeness 92.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     83.67
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C14(H14), C3(H3), C5(H5), C18(H18), C6(H6), C16(H16)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_olex2_date_sample_data_collection 2021-06-22
_olex2_date_sample_submission    2021-06-22
_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 3.314
_oxdiff_exptl_absorpt_empirical_full_min 0.628