Co-crystallization studies of the syn- and anti-atropisomers of triphenyl-based perfluorinated halogen bond donors with halides
Stoesser, Julian; Engelage, Elric; Huber, Stefan; CrystEngComm  (2022) –; doi:10.1039/D2CE00973K

data_7245539
_publ_section_title
;
 Co-crystallization studies of the syn- and anti-atropisomers of
 triphenyl-based perfluorinated halogen bond donors with halides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00973K
_journal_year                    2022
_chemical_formula_moiety
'3(C18 F12 I2), 2(C9 H18 N3), 2(C H2 Cl2), 2(Cl)'
_chemical_formula_sum            'C74 H40 Cl6 F36 I6 N6'
_chemical_formula_weight         2671.05
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-27 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                75.6600(10)
_cell_angle_beta                 82.4300(10)
_cell_angle_gamma                88.6400(10)
_cell_formula_units_Z            1
_cell_length_a                   7.867
_cell_length_b                   12.37760(10)
_cell_length_c                   22.96440(10)
_cell_measurement_reflns_used    7555
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.7
_cell_volume                     2147.50(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_molecular_graphics
;
 Diamond 4 - Crystal and Molecular Structure Visualization
  Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, 
  Kreuzherrenstr. 102, 53227 Bonn, Germany
  http://www.crystalimpact.com/diamond
 Mercury CSD 2.0 - New Features for the Visualization 
 and Investigation of Crystal Structures
  C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe,
  E. Pidcock, 
  L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, 
  J. Appl. Cryst., 41, 466-470, 2008
;
_computing_publication_material
'WinGX L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
 shelXT  G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr.,
 2008, 64, 112-122.
 shelXle C. B. Huebschle, G. M. Sheldrick and B. Dittrich J. Appl. Cryst.
  (2011). 44, 1281-1284
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -86.00 -40.00   0.50    0.05    --  -47.45 125.00  41.00   92
  2  \w    -74.00 -49.00   0.50    0.10    --  -86.25 125.00  41.00   50
  3  \w    -36.00 -11.00   0.50    0.05    --    6.00 123.00 139.11   50
  4  \w    -30.00  -4.00   0.50    0.05    --   10.00 112.00  52.13   52
  5  \w    -17.00   9.00   0.50    0.05    --   18.00 102.00 -34.35   52
  6  \w     13.00  38.00   0.50    0.05    --   42.00  90.00  15.06   50
  7  \w     30.00  61.00   0.50    0.05    --   54.00  80.00  -3.67   62
  8  \w     42.00  72.00   0.50    0.05    --   66.00  79.00  23.30   60
  9  \w     48.00  74.00   0.50    0.05    --   47.45  38.00  30.00   52
 10  \w     45.00 115.00   0.50    0.05    --   47.45  19.00 -30.00  140
 11  \w    100.00 126.00   0.50    0.05    --   54.00  77.00 -64.12   52
 12  \w    101.00 126.00   0.50    0.05    --   54.00  80.00  -3.67   50
 13  \w    114.00 139.00   0.50    0.05    --   66.00  79.00  23.30   50
 14  \w     96.00 135.00   0.50    0.10    --  106.49 125.00  41.00   78
 15  \w    126.00 152.00   0.50    0.10    --  106.49  77.00 120.00   52
 16  \w    146.00 174.00   0.50    0.10    --  106.49  77.00 150.00   56
 17  \w    145.00 174.00   0.50    0.10    --  106.49  77.00  60.00   58
 18  \w    108.00 165.00   0.50    0.10    --  106.49  45.00 150.00  114
 19  \w     93.00 140.00   0.50    0.10    --  106.49  77.00 150.00   94
 20  \w     84.00 124.00   0.50    0.10    --  106.49  77.00 120.00   80
 21  \w     86.00 176.00   0.50    0.10    --  106.49  77.00  90.00  180
 22  \w     93.00 175.00   0.50    0.10    --  106.49  61.00   0.00  164
 23  \w    145.00 171.00   0.50    0.10    --  106.49  61.00-120.00   52
 24  \w    147.00 178.00   0.50    0.10    --  106.49  77.00-180.00   62
 25  \w    100.00 125.00   0.50    0.10    --  106.49 147.00-152.00   50
 26  \w     76.00 102.00   0.50    0.05    --   58.00  79.00-121.83   52
 27  \w     70.00  96.00   0.50    0.05    --   58.00  79.00-163.15   52
 28  \w     42.00  79.00   0.50    0.05    --   66.00  79.00 -80.77   74
 29  \w     50.00  76.00   0.50    0.05    --   70.00  74.00 -66.70   52
 30  \w     47.00  73.00   0.50    0.05    --   70.00  78.00-103.61   52
 31  \w     44.00  69.00   0.50    0.05    --   66.00  76.00-138.88   50
 32  \w     35.00  70.00   0.50    0.05    --   47.45  19.00-180.00   70
 33  \w     34.00  65.00   0.50    0.05    --   58.00  79.00-121.83   62
 34  \w     34.00  59.00   0.50    0.05    --   58.00  79.00-163.15   50
 35  \w      3.00  32.00   0.50    0.05    --   34.00  94.00-148.96   58
 36  \w     13.00  38.00   0.50    0.05    --   42.00  91.00-102.96   50
 37  \w     31.00  75.00   0.50    0.05    --   54.00  77.00 -64.12   88
 38  \w     44.00  69.00   0.50    0.05    --   66.00  77.00  -3.88   50
 39  \w     33.00  58.00   0.50    0.05    --   54.00  77.00 -42.74   50
 40  \w     33.00  78.00   0.50    0.05    --   54.00  77.00  48.52   90
 41  \w     60.00  85.00   0.50    0.05    --   50.00  76.00 131.47   50
 42  \w     44.00  70.00   0.50    0.05    --   66.00  76.00  88.31   52
 43  \w     42.00  98.00   0.50    0.05    --   66.00  79.00 122.08  112
 44  \w     85.00 137.00   0.50    0.10    --  106.49  77.00  60.00  104
 45  \w     97.00 173.00   0.50    0.10    --  106.49  61.00 -30.00  152
 46  \w     99.00 173.00   0.50    0.10    --  106.49  61.00 -90.00  148
 47  \w     94.00 153.00   0.50    0.10    --  106.49  61.00-180.00  118
 48  \w     86.00 128.00   0.50    0.10    --  106.49  77.00-180.00   84
 49  \w     92.00 133.00   0.50    0.10    --  106.49  61.00-120.00   82
 50  \w     95.00 150.00   0.50    0.10    --  106.49  45.00 -30.00  110
 51  \w     85.00 178.00   0.50    0.10    --  106.49  77.00-150.00  186
 52  \w     86.00 166.00   0.50    0.10    --  106.49  77.00  30.00  160
 53  \w     45.00  74.00   0.50    0.10    --  106.49 -61.00 -30.00   58
 54  \w     76.00 102.00   0.50    0.10    --  106.49 -94.00   0.00   52
 55  \w     84.00 110.00   0.50    0.10    --  106.49-125.00 -36.00   52
 56  \w     68.00 107.00   0.50    0.10    --  106.49-103.00-135.87   78
 57  \w     81.00 106.00   0.50    0.10    --  106.49 -77.00-180.00   50
 58  \w     36.00 105.00   0.50    0.10    --  106.49 -94.00 -90.00  138
 59  \w     35.00  92.00   0.50    0.05    --   47.45-125.00 -36.00  114
 60  \w     34.00  73.00   0.50    0.10    --  106.49 -94.00   0.00   78
 61  \w     36.00 109.00   0.50    0.10    --  106.49-125.00   0.00  146
 62  \w     54.00  84.00   0.50    0.10    --  106.49-125.00 120.00   60
 63  \w     76.00 126.00   0.50    0.10    --  106.49-147.00 157.00  100
 64  \w     55.00  80.00   0.50    0.05    --   47.45-147.00 157.00   50
 65  \w     46.00  72.00   0.50    0.10    --  106.49 -94.00 150.00   52
 66  \w     37.00 100.00   0.50    0.10    --  106.49-125.00  90.00  126
 67  \w     37.00  74.00   0.50    0.10    --  106.49 -61.00 120.00   74
 68  \w     15.00  40.00   0.50    0.05    --   42.00  86.00 112.19   50
 69  \w     28.00  56.00   0.50    0.05    --   50.00  76.00 131.47   56
 70  \w     39.00  72.00   0.50    0.05    --   62.00  77.00 160.05   66
 71  \w     33.00  59.00   0.50    0.05    --   54.00  76.00 169.63   52
 72  \w     36.00  96.00   0.50    0.05    --   58.00  76.00  76.68  120
 73  \w     37.00  74.00   0.50    0.10    --  106.49 -61.00-180.00   74
 74  \w     38.00  76.00   0.50    0.10    --  106.49 -77.00-180.00   76
 75  \w     41.00 107.00   0.50    0.10    --  106.49-125.00-180.00  132
 76  \w    -78.00 -53.00   0.50    0.10    --  -74.00 -72.00 -55.46   50
 77  \w    -78.00 -53.00   0.50    0.10    --  -74.00 -73.00 -31.44   50
 78  \w    -82.00 -52.00   0.50    0.10    --  -70.00 -69.00  30.80   60
 79  \w    -90.00 -61.00   0.50    0.10    --  -82.00 -72.00  62.68   58
 80  \w    -90.00 -64.00   0.50    0.10    --  -86.25 -77.00   8.79   52
 81  \w    -89.00 -63.00   0.50    0.10    --  -86.25 -77.00 -30.00   52
 82  \w    -90.00 -65.00   0.50    0.10    --  -86.25 -75.00 -68.31   50
 83  \w    -89.00 -64.00   0.50    0.10    --  -86.00 -74.00-119.55   50
 84  \w    -81.00 -54.00   0.50    0.10    --  -74.00 -73.00-177.56   54
 85  \w    -87.00 -62.00   0.50    0.10    --  -86.25 -80.00-139.68   50
 86  \w    -89.00 -64.00   0.50    0.10    --  -86.25 -75.00-133.22   50
 87  \w    -90.00 -62.00   0.50    0.10    --  -86.25 -80.00 -94.78   56
 88  \w    -91.00 -66.00   0.50    0.10    --  -86.25 -70.00 -56.62   50
 89  \w    -99.00 -69.00   0.50    0.10    --  -86.25 -63.00 -63.01   60
 90  \w    -98.00 -66.00   0.50    0.10    --  -86.25 -71.00 -16.95   64
 91  \w    -95.00 -64.00   0.50    0.10    --  -86.25 -76.00  35.94   62
 92  \w   -102.00 -66.00   0.50    0.10    --  -86.25 -70.00  39.45   72
 93  \w    -89.00 -64.00   0.50    0.10    --  -86.25 -76.00 103.67   50
 94  \w    -77.00 -52.00   0.50    0.10    --  -74.00 -75.00 139.19   50
 95  \w    -77.00 -52.00   0.50    0.10    --  -74.00 -74.00 157.41   50
 96  \w    -89.00 -64.00   0.50    0.10    --  -86.25 -77.00 129.49   50
 97  \w    -92.00 -63.00   0.50    0.10    --  -86.25 -77.00 150.00   58
 98  \w   -100.00 -66.00   0.50    0.10    --  -86.25 -70.00 130.67   68
 99  \w   -105.00 -66.00   0.50    0.10    --  -86.25 -70.00 105.89   78
100  \w   -113.00 -88.00   0.50    0.05    --  -47.45-147.00 157.00   50
101  \w   -100.00 -62.00   0.50    0.05    --  -47.45 147.00-152.00   76
102  \w    -50.00 -25.00   0.50    0.05    --  -47.45 147.00-152.00   50
103  \w    -87.00 -62.00   0.50    0.10    --  -86.25 147.00-152.00   50
104  \w   -118.00 -67.00   0.50    0.10    --  -86.25 -73.00  65.01  102
105  \w    -98.00 -65.00   0.50    0.10    --  -86.25 -73.00  14.67   66
106  \w   -120.00 -80.00   0.50    0.05    --  -47.45-125.00 -36.00   80
107  \w   -116.00 -91.00   0.50    0.10    --  -86.25-125.00 -36.00   50
108  \w   -107.00 -68.00   0.50    0.10    --  -86.25 -65.00 -92.25   78
109  \w   -106.00 -63.00   0.50    0.10    --  -86.25 -77.00-180.00   86
110  \w   -126.00 -65.00   0.50    0.10    --  -86.25 -74.00-162.52  122
111  \w   -144.00-118.00   0.50    0.10    --  -86.25 -77.00 -30.00   52
112  \w   -154.00-129.00   0.50    0.10    --  -86.25 -70.00  39.45   50
113  \w   -142.00-116.00   0.50    0.10    --  -86.25 -76.00  35.94   52
114  \w   -111.00 -63.00   0.50    0.10    --  -86.25 -77.00  90.00   96
115  \w   -129.00-104.00   0.50    0.10    --  -86.25-147.00 157.00   50
116  \w   -148.00-123.00   0.50    0.10    --  -86.25 -77.00  90.00   50
117  \w   -155.00-130.00   0.50    0.10    --  -86.25 -70.00 105.89   50
118  \w   -147.00-121.00   0.50    0.10    --  -86.25 -77.00   8.79   52
119  \w   -150.00-125.00   0.50    0.10    --  -86.25 -80.00 -94.78   50
;
_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      0.0239728000
_diffrn_orient_matrix_UB_12      0.0195270000
_diffrn_orient_matrix_UB_13      -0.0695040000
_diffrn_orient_matrix_UB_21      0.1539530000
_diffrn_orient_matrix_UB_22      0.0777143000
_diffrn_orient_matrix_UB_23      -0.0046895000
_diffrn_orient_matrix_UB_31      0.1214649000
_diffrn_orient_matrix_UB_32      -0.1004200000
_diffrn_orient_matrix_UB_33      0.0049025000
_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  0.0479
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            56202
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.494
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_min         3.736
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.897
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_correction_T_min  0.019
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.29a (Rigaku Oxford Diffraction, 2018)
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            'translucent colourless'
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_description       plate
_exptl_crystal_F_000             1270
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.089
_refine_diff_density_max         1.496
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         7555
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+2.1905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7249
_reflns_number_total             7555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00973k2.cif
_cod_data_source_block           anti-p-1-TDACl
_cod_database_code               7245539
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.704
_oxdiff_exptl_absorpt_empirical_full_max 1.590
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_shelx_res_checksum              4253
_shelx_hkl_checksum              21362