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_7245537
_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), C8 H20 N, Br'
_chemical_formula_sum            'C44 H20 Br F24 I4 N'
_chemical_formula_weight         1606.12
_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 space'
_atom_sites_solution_secondary   difmap
_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                80.102(3)
_cell_angle_beta                 89.936(3)
_cell_angle_gamma                85.987(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2153(4)
_cell_length_b                   14.8333(6)
_cell_length_c                   33.3212(9)
_cell_measurement_reflns_used    17224
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.5
_cell_volume                     4961.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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      0.00  28.00   1.00    1.75    --   36.00  88.00-113.19   28
  2  \w      2.00  28.00   1.00    1.75    --   40.00  92.00  35.77   26
  3  \w     18.00 117.00   1.00    1.75    --   42.53  37.00 -90.00   99
  4  \w      2.00  91.00   1.00    1.75    --   42.53-125.00 -30.00   89
  5  \w      6.00  88.00   1.00    1.75    --   42.53-128.00 145.00   82
  6  \w     19.00 115.00   1.00    1.75    --   42.53  37.00  60.00   96
  7  \w     15.00 111.00   1.00    1.75    --   42.53  57.00 150.00   96
  8  \w     14.00  39.00   1.00    1.75    --   48.00  82.00 -64.55   25
  9  \w     18.00  43.00   1.00    1.75    --   52.00  82.00 100.73   25
 10  \w     18.00  43.00   1.00    1.75    --   52.00  81.00-167.63   25
 11  \w     18.00  43.00   1.00    1.75    --   52.00  81.00  14.01   25
 12  \w     23.00  48.00   1.00    1.75    --   56.00  78.00 -29.52   25
 13  \w     28.00  55.00   1.00    1.75    --   60.00  76.00 136.07   27
 14  \w     27.00  53.00   1.00    1.75    --   60.00  77.00  49.45   26
 15  \w     33.00 133.00   1.00    1.75    --   64.00  75.00 -40.34  100
 16  \w     35.00  61.00   1.00    1.75    --   68.00  77.00  67.81   26
 17  \w     35.00  61.00   1.00    1.75    --   68.00  77.00-148.99   26
 18  \w    122.00 147.00   1.00    1.75    --   72.00  75.00  -1.84   25
 19  \w    116.00 146.00   1.00    1.75    --   72.00  77.00 167.70   30
 20  \w    105.00 140.00   1.00    1.75    --   72.00  76.00 133.90   35
 21  \w     81.00 107.00   1.00    1.75    --   72.00  77.00-105.88   26
 22  \w     40.00  67.00   1.00    1.75    --   72.00  75.00  -1.84   27
 23  \w     40.00  66.00   1.00    1.75    --   72.00  76.00 133.90   26
 24  \w     39.00  71.00   1.00    1.75    --   72.00  77.00 167.70   32
 25  \w     40.00  69.00   1.00    1.75    --   72.00  77.00-105.88   29
 26  \w    122.00 152.00   1.00    2.70    --   76.00  77.00 -30.23   30
 27  \w     43.00  75.00   1.00    2.70    --   76.00  77.00 -30.23   32
 28  \w     43.00  68.00   1.00    2.70    --   76.00  77.00  25.48   25
 29  \w     44.00  97.00   1.00    2.70    --   76.00  76.00  93.40   53
 30  \w     44.00  72.00   1.00    2.70    --   76.00  76.00-141.85   28
 31  \w    119.00 146.00   1.00    2.70    --   84.00  77.00  32.95   27
 32  \w     51.00  77.00   1.00    2.70    --   84.00  77.00  32.95   26
 33  \w     67.00 111.00   1.00    2.70    --   96.00  62.00 -92.62   44
 34  \w    114.00 155.00   1.00    2.70    --  108.04  77.00  90.00   41
 35  \w    112.00 157.00   1.00    2.70    --  108.04  77.00 120.00   45
 36  \w     86.00 113.00   1.00    2.70    --  108.04  61.00  60.00   27
 37  \w     79.00 108.00   1.00    2.70    --  108.04  61.00 120.00   29
 38  \w     79.00 107.00   1.00    2.70    --  108.04  61.00 150.00   28
 39  \w     75.00 158.00   1.00    2.70    --  108.04  77.00 150.00   83
 40  \w     75.00 101.00   1.00    2.70    --  108.04  77.00   0.00   26
 41  \w     75.00 149.00   1.00    2.70    --  108.04  77.00  30.00   74
 42  \w     79.00 155.00   1.00    2.70    --  108.04  61.00 -90.00   76
 43  \w     81.00 158.00   1.00    2.70    --  108.04 125.00 -30.00   77
 44  \w     75.00 147.00   1.00    2.70    --  108.04  77.00 -60.00   72
 45  \w     75.00 158.00   1.00    2.70    --  108.04  77.00  60.00   83
 46  \w     75.00 101.00   1.00    2.70    --  108.04  77.00  90.00   26
 47  \w     75.00 101.00   1.00    2.70    --  108.04  77.00 120.00   26
 48  \w     75.00 101.00   1.00    2.70    --  108.04  77.00 -90.00   26
 49  \w     75.00 155.00   1.00    2.70    --  108.04  77.00 -30.00   80
 50  \w     75.00 158.00   1.00    2.70    --  108.04  77.00-180.00   83
 51  \w     75.00 158.00   1.00    2.70    --  108.04  77.00-150.00   83
 52  \w     47.00 134.00   1.00    2.70    --  108.04 -61.00 -60.00   87
 53  \w     80.00 109.00   1.00    2.70    --  108.04 -94.00 -30.00   29
 54  \w     34.00  61.00   1.00    2.70    --  108.04 -94.00 -30.00   27
 55  \w     28.00 104.00   1.00    2.70    --  108.04 -94.00 -90.00   76
 56  \w     27.00 109.00   1.00    2.70    --  108.04 -94.00-180.00   82
 57  \w     37.00 117.00   1.00    2.70    --  108.04-128.00 145.00   80
 58  \w     25.00  73.00   1.00    2.70    --  108.04 -94.00 150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0009421000
_diffrn_orient_matrix_UB_12      -0.0256152000
_diffrn_orient_matrix_UB_13      0.0467190000
_diffrn_orient_matrix_UB_21      0.0996385000
_diffrn_orient_matrix_UB_22      0.0718318000
_diffrn_orient_matrix_UB_23      0.0027086000
_diffrn_orient_matrix_UB_31      -0.1135331000
_diffrn_orient_matrix_UB_32      0.0729739000
_diffrn_orient_matrix_UB_33      0.0020972000
_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  0.0605
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            77496
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.497
_diffrn_reflns_theta_max         66.497
_diffrn_reflns_theta_min         3.523
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.824
_exptl_absorpt_correction_T_max  0.536
_exptl_absorpt_correction_T_min  0.038
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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            colourless
_exptl_crystal_density_diffrn    2.150
_exptl_crystal_description       prism
_exptl_crystal_F_000             3016
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.065
_refine_diff_density_max         1.600
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1341
_refine_ls_number_reflns         17224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+41.2935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14454
_reflns_number_total             17224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00973k2.cif
_cod_data_source_block           syn-m-1-TEABr
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245537
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.657
_oxdiff_exptl_absorpt_empirical_full_max 2.150
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              88487
_shelx_hkl_checksum              86681