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_7245538
_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, I'
_chemical_formula_sum            'C45 H18 F24 I5 N3'
_chemical_formula_weight         1691.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 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                 97.1660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.59520(10)
_cell_length_b                   7.87140(10)
_cell_length_c                   26.3715(2)
_cell_measurement_reflns_used    8240
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.4
_cell_volume                     2594.10(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      170.02(14)
_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    -23.00  27.00   0.50    0.05    --  -47.45  19.00  30.00  100
  2  \w    -34.00  26.00   0.50    0.05    --  -47.45  38.00  60.00  120
  3  \w    -46.00 -20.00   0.50    0.25    --  -86.25  45.00   0.00   52
  4  \w    -66.00 -41.00   0.50    0.25    --  -86.25  61.00  90.00   50
  5  \w   -114.00 -79.00   0.50    0.25    --  -86.25 -15.00   0.00   70
  6  \w   -121.00 -36.00   0.50    0.05    --  -47.45 -19.00-120.00  170
  7  \w    -43.00 -18.00   0.50    0.25    --  -86.25  45.00-180.00   50
  8  \w    -44.00 -16.00   0.50    0.25    --  -86.25  45.00-150.00   56
  9  \w   -100.00 -73.00   0.50    0.05    --  -47.45-125.00-120.00   54
 10  \w    -19.00  62.00   0.50    0.05    --   47.45 -57.00-150.00  162
 11  \w     37.00  67.00   0.50    0.25    --  106.49 -94.00 -60.00   60
 12  \w     74.00 107.00   0.50    0.25    --  106.49 -77.00 -60.00   66
 13  \w     78.00 105.00   0.50    0.25    --  106.49 -94.00 -90.00   54
 14  \w     74.00  99.00   0.50    0.25    --  106.49-125.00-120.00   50
 15  \w     75.00 105.00   0.50    0.25    --  106.49 -94.00 -60.00   60
 16  \w     80.00 105.00   0.50    0.25    --  106.49 -94.00 -30.00   50
 17  \w     59.00 111.00   0.50    0.25    --  106.49-125.00  60.00  104
 18  \w     80.00 108.00   0.50    0.25    --  106.49 -77.00 120.00   56
 19  \w     72.00 104.00   0.50    0.25    --  106.49 -94.00 120.00   64
 20  \w     62.00  88.00   0.50    0.05    --   47.45-125.00  90.00   52
 21  \w     34.00  72.00   0.50    0.25    --  106.49 -61.00 120.00   76
 22  \w     35.00  62.00   0.50    0.25    --  106.49 -77.00 120.00   54
 23  \w     34.00  74.00   0.50    0.25    --  106.49 -61.00 150.00   80
 24  \w     36.00  95.00   0.50    0.25    --  106.49 -77.00  60.00  118
 25  \w     34.00  67.00   0.50    0.25    --  106.49 -77.00 -60.00   66
 26  \w     38.00  63.00   0.50    0.25    --  106.49 -94.00 -90.00   50
 27  \w     34.00  59.00   0.50    0.25    --  106.49 -61.00-120.00   50
 28  \w     36.00  70.00   0.50    0.25    --  106.49 -61.00 -60.00   68
 29  \w     39.00 107.00   0.50    0.25    --  106.49-103.00-118.91  136
 30  \w    113.00 151.00   0.50    0.25    --  106.49  30.00   0.00   76
 31  \w     94.00 159.00   0.50    0.25    --  106.49  30.00  30.00  130
 32  \w    102.00 171.00   0.50    0.25    --  106.49  30.00 120.00  138
 33  \w     94.00 176.00   0.50    0.25    --  106.49  30.00 -90.00  164
 34  \w    152.00 178.00   0.50    0.25    --  106.49  45.00-120.00   52
 35  \w     93.00 177.00   0.50    0.25    --  106.49  15.00-120.00  168
 36  \w     34.00 104.00   0.50    0.25    --  106.49 -94.00  60.00  140
 37  \w   -115.00 -73.00   0.50    0.05    --  -47.45-125.00-150.00   84
 38  \w   -161.00-131.00   0.50    0.25    --  -86.25 -15.00   0.00   60
;
_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      0.0775543000
_diffrn_orient_matrix_UB_12      0.1206507000
_diffrn_orient_matrix_UB_13      0.0322805000
_diffrn_orient_matrix_UB_21      -0.0414005000
_diffrn_orient_matrix_UB_22      -0.0653223000
_diffrn_orient_matrix_UB_23      0.0489830000
_diffrn_orient_matrix_UB_31      0.0864299000
_diffrn_orient_matrix_UB_32      -0.1396064000
_diffrn_orient_matrix_UB_33      0.0049398000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26783
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        66.482
_diffrn_reflns_theta_max         66.482
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    24.674
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.164
_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 amber'
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_description       block
_exptl_crystal_F_000             1580
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.093
_refine_diff_density_max         1.071
_refine_diff_density_min         -2.110
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.018(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         8240
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0874P)^2^+0.4251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.801
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                8140
_reflns_number_total             8240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00973k2.cif
_cod_data_source_block           anti-m-1-TDAI
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7245538
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.842
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              53749
_shelx_hkl_checksum              81471