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_7245531
_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(Br)
;
_chemical_formula_sum            'C74 H40 Br2 Cl4 F36 I6 N6'
_chemical_formula_weight         2760.14
_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                76.3010(10)
_cell_angle_beta                 81.9550(10)
_cell_angle_gamma                88.1070(10)
_cell_formula_units_Z            1
_cell_length_a                   7.82960(10)
_cell_length_b                   12.4477(2)
_cell_length_c                   23.1195(2)
_cell_measurement_reflns_used    7603
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.7
_cell_volume                     2167.60(5)
_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 0.994
_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    -31.00  -5.00   0.50    0.17    --  -47.45 109.00 167.00   52
  2  \w     23.00  70.00   0.50    0.17    --   47.45-109.00  72.00   94
  3  \w    -76.00 -40.00   0.50    0.60    --  -86.25 109.00 167.00   72
  4  \w   -113.00 -83.00   0.50    0.60    --  -86.25-109.00  72.00   60
  5  \w    105.00 162.00   0.50    0.60    --  106.49 109.00 167.00  114
  6  \w     67.00 107.00   0.50    0.60    --  106.49-109.00  72.00   80
  7  \w    -22.00  28.00   0.50    0.17    --  -47.45  19.00-120.00  100
  8  \w   -120.00 -75.00   0.50    0.17    --  -47.45-125.00  30.00   90
  9  \w    -85.00 -16.00   0.50    0.17    --  -47.45 125.00 -90.00  138
 10  \w   -120.00 -36.00   0.50    0.17    --  -47.45 -57.00  90.00  168
 11  \w    -22.00  11.00   0.50    0.17    --  -47.45  19.00-150.00   66
 12  \w    -17.00   9.00   0.50    0.17    --   47.45 -57.00-180.00   52
 13  \w     27.00  62.00   0.50    0.17    --   47.45 -57.00-180.00   70
 14  \w    -43.00 -14.00   0.50    0.60    --  -86.25  45.00-120.00   58
 15  \w   -149.00 -97.00   0.50    0.60    --  -86.25 -45.00 -90.00  104
 16  \w   -141.00-115.00   0.50    0.60    --  -86.25 -94.00-150.00   52
 17  \w   -109.00 -83.00   0.50    0.60    --  -86.25 -94.00-150.00   52
 18  \w   -139.00-104.00   0.50    0.60    --  -86.25 -30.00 120.00   70
 19  \w     39.00 105.00   0.50    0.60    --  106.49-125.00  60.00  132
 20  \w     36.00  95.00   0.50    0.60    --  106.49 -94.00  90.00  118
 21  \w     76.00 110.00   0.50    0.60    --  106.49-125.00-180.00   68
 22  \w     42.00  72.00   0.50    0.60    --  106.49-125.00-180.00   60
 23  \w     41.00  82.00   0.50    0.60    --  106.49 -77.00-180.00   82
 24  \w    110.00 178.00   0.50    0.60    --  106.49  45.00  60.00  136
 25  \w     81.00 106.00   0.50    0.60    --  106.49 -77.00  60.00   50
 26  \w     53.00  99.00   0.50    0.60    --  106.49 -94.00 -30.00   92
 27  \w    125.00 178.00   0.50    0.60    --  106.49  30.00 150.00  106
 28  \w     35.00  74.00   0.50    0.60    --  106.49 -61.00 -60.00   78
 29  \w     45.00  71.00   0.50    0.60    --  106.49 -77.00  60.00   52
 30  \w     37.00 108.00   0.50    0.60    --  106.49-125.00 -60.00  142
 31  \w     47.00  73.00   0.50    0.60    --  106.49 -94.00-120.00   52
 32  \w     70.00  96.00   0.50    0.60    --  106.49 -94.00 -60.00   52
 33  \w     37.00  62.00   0.50    0.60    --  106.49 -61.00 150.00   50
 34  \w     36.00  62.00   0.50    0.60    --  106.49 -94.00-180.00   52
 35  \w     94.00 147.00   0.50    0.60    --  106.49  30.00-120.00  106
 36  \w     98.00 175.00   0.50    0.60    --  106.49  45.00 120.00  154
 37  \w     98.00 152.00   0.50    0.60    --  106.49  30.00 120.00  108
 38  \w     35.00  66.00   0.50    0.60    --  106.49 -61.00 -30.00   62
 39  \w     74.00 104.00   0.50    0.60    --  106.49 -94.00-180.00   60
 40  \w     52.00 129.00   0.50    0.60    --  106.49-149.00  -0.13  154
 41  \w     48.00  73.00   0.50    0.60    --  106.49 -61.00-150.00   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      0.1802674000
_diffrn_orient_matrix_UB_12      0.0367086000
_diffrn_orient_matrix_UB_13      -0.0336631000
_diffrn_orient_matrix_UB_21      0.0788531000
_diffrn_orient_matrix_UB_22      -0.0436871000
_diffrn_orient_matrix_UB_23      0.0585667000
_diffrn_orient_matrix_UB_31      0.0278325000
_diffrn_orient_matrix_UB_32      -0.1138908000
_diffrn_orient_matrix_UB_33      -0.0151479000
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24385
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.496
_diffrn_reflns_theta_max         66.496
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.225
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.113
_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    2.114
_exptl_crystal_description       needle
_exptl_crystal_F_000             1306
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         7603
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0530P)^2^+1.3199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6984
_reflns_number_total             7603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00973k2.cif
_cod_data_source_block           anti-p-1-TDABr
_cod_database_code               7245531
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.642
_oxdiff_exptl_absorpt_empirical_full_max 2.442
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              11825
_shelx_hkl_checksum              7892