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_7245533
_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         '2(C18 F12 I2), C9 H18 N3, Cl'
_chemical_formula_sum            'C45 H18 Cl F24 I4 N3'
_chemical_formula_weight         1599.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 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                90
_cell_angle_beta                 91.1507(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.56024(12)
_cell_length_b                   8.05461(4)
_cell_length_c                   24.62605(10)
_cell_measurement_reflns_used    7403
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.5
_cell_volume                     5068.93(4)
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -46.00 -21.00   0.50    0.06    --  -47.45 118.00-107.00   50
  2  \w    -83.00 -31.00   0.50    0.06    --  -47.45 158.00  46.00  104
  3  \w     73.00 119.00   0.50    0.06    --   47.45 158.00  46.00   92
  4  \w     64.00  89.00   0.50    0.06    --   47.45-158.00  12.00   50
  5  \w     37.00  62.00   0.50    0.06    --   47.45-118.00 166.00   50
  6  \w    -81.00 -46.00   0.50    0.23    --  -86.25 118.00-107.00   70
  7  \w    -93.00 -68.00   0.50    0.23    --  -86.25 158.00  46.00   50
  8  \w     63.00  88.00   0.50    0.23    --  106.49-158.00  12.00   50
  9  \w     47.00  72.00   0.50    0.23    --  106.49-118.00 166.00   50
 10  \w    127.00 172.00   0.50    0.23    --  106.49 118.00-107.00   90
 11  \w     95.00 134.00   0.50    0.23    --  106.49-158.00  12.00   78
 12  \w   -118.00 -83.00   0.50    0.06    --  -47.45-125.00 -90.00   70
 13  \w   -115.00 -85.00   0.50    0.06    --  -47.45-125.00  30.00   60
 14  \w   -100.00 -74.00   0.50    0.06    --  -47.45-125.00  60.00   52
 15  \w    -22.00  27.00   0.50    0.06    --  -47.45  19.00 -90.00   98
 16  \w   -118.00 -73.00   0.50    0.06    --  -47.45-125.00-180.00   90
 17  \w    -43.00 -15.00   0.50    0.23    --  -86.25  45.00 120.00   56
 18  \w    -46.00 -13.00   0.50    0.23    --  -86.25  61.00  30.00   66
 19  \w    -40.00 -15.00   0.50    0.23    --  -86.25  45.00-120.00   50
 20  \w    -48.00 -17.00   0.50    0.23    --  -86.25  45.00-150.00   62
 21  \w   -121.00 -96.00   0.50    0.23    --  -86.25-158.00  12.00   50
 22  \w     41.00  68.00   0.50    0.23    --  106.49 -61.00 -30.00   54
 23  \w     35.00  73.00   0.50    0.23    --  106.49 -61.00   0.00   76
 24  \w     39.00  64.00   0.50    0.23    --  106.49-125.00 120.00   50
 25  \w     69.00 111.00   0.50    0.23    --  106.49-125.00 120.00   84
 26  \w     40.00  70.00   0.50    0.23    --  106.49 -61.00-150.00   60
 27  \w     38.00  74.00   0.50    0.23    --  106.49 -61.00 -60.00   72
 28  \w     66.00 104.00   0.50    0.23    --  106.49 -77.00 120.00   76
 29  \w     40.00  73.00   0.50    0.23    --  106.49 -61.00  30.00   66
 30  \w     49.00  74.00   0.50    0.23    --  106.49 -61.00  60.00   50
 31  \w    101.00 173.00   0.50    0.23    --  106.49  15.00 -60.00  144
 32  \w     97.00 176.00   0.50    0.23    --  106.49  30.00-180.00  158
 33  \w     46.00  71.00   0.50    0.23    --  106.49 -61.00 150.00   50
 34  \w    124.00 159.00   0.50    0.23    --  106.49  83.00 175.00   70
 35  \w     -9.00  17.00   0.50    0.06    --  -47.45  57.00-180.00   52
 36  \w    -23.00  22.00   0.50    0.06    --  -47.45  19.00-120.00   90
 37  \w    -61.00 -13.00   0.50    0.06    --  -47.45  57.00-180.00   96
 38  \w     -3.00  22.00   0.50    0.06    --  -47.45  19.00 -30.00   50
 39  \w    -22.00  28.00   0.50    0.06    --   47.45 -19.00  30.00  100
 40  \w     45.00  96.00   0.50    0.06    --   47.45  38.00 -90.00  102
 41  \w    -68.00 -43.00   0.50    0.23    --  -86.25  61.00 150.00   50
 42  \w   -138.00 -73.00   0.50    0.23    --  -86.25 -45.00 -30.00  130
 43  \w     95.00 177.00   0.50    0.23    --  106.49  61.00 -60.00  164
 44  \w    153.00 178.00   0.50    0.23    --  106.49  45.00  90.00   50
 45  \w     92.00 148.00   0.50    0.23    --  106.49  61.00 120.00  112
 46  \w     94.00 122.00   0.50    0.23    --  106.49  30.00-120.00   56
 47  \w    131.00 175.00   0.50    0.23    --  106.49  30.00-120.00   88
 48  \w    107.00 141.00   0.50    0.23    --  106.49  45.00-120.00   68
 49  \w    103.00 129.00   0.50    0.23    --  106.49  45.00  90.00   52
 50  \w     95.00 121.00   0.50    0.23    --  106.49  45.00 150.00   52
 51  \w     35.00  65.00   0.50    0.23    --  106.49 -94.00 -30.00   60
 52  \w    138.00 164.00   0.50    0.23    --  106.49  15.00 -30.00   52
 53  \w     99.00 126.00   0.50    0.23    --  106.49  15.00 -30.00   54
 54  \w    126.00 163.00   0.50    0.23    --  106.49  45.00 150.00   74
 55  \w     37.00 100.00   0.50    0.23    --  106.49 -77.00   0.00  126
 56  \w     94.00 120.00   0.50    0.23    --  106.49  45.00 120.00   52
 57  \w     34.00  59.00   0.50    0.23    --  106.49 -61.00  90.00   50
 58  \w     46.00  72.00   0.50    0.23    --  106.49 -61.00 120.00   52
 59  \w     45.00  71.00   0.50    0.23    --  106.49 -77.00  60.00   52
 60  \w     74.00 128.00   0.50    0.23    --  106.49 -83.00  54.00  108
;
_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      0.0520655000
_diffrn_orient_matrix_UB_12      0.0711694000
_diffrn_orient_matrix_UB_13      0.0223677000
_diffrn_orient_matrix_UB_21      0.0293103000
_diffrn_orient_matrix_UB_22      -0.1517175000
_diffrn_orient_matrix_UB_23      -0.0223254000
_diffrn_orient_matrix_UB_31      0.0080482000
_diffrn_orient_matrix_UB_32      0.0921554000
_diffrn_orient_matrix_UB_33      -0.0540044000
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34691
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        66.499
_diffrn_reflns_theta_max         66.499
_diffrn_reflns_theta_min         3.459
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.957
_exptl_absorpt_correction_T_max  0.390
_exptl_absorpt_correction_T_min  0.012
_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            'clear colourless'
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_description       block
_exptl_crystal_F_000             3016
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.118
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_coef       0.00030(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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         7403
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0689P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.656
_reflns_Friedel_fraction_max     0.656
_reflns_number_gt                7357
_reflns_number_total             7403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00973k2.cif
_cod_data_source_block           anti-m-1-TDACl
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               7245533
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.814
_oxdiff_exptl_absorpt_empirical_full_max 1.318
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              77741
_shelx_hkl_checksum              5614