One dimensional halogen bond design: Br⋯N versus I⋯N with fluoroarenes
Peloquin, Andrew J.; McMillen, Colin D.; Pennington, William T.; CrystEngComm 23 (2021) 6098–6106; doi:10.1039/D1CE00864A

data_7243334
_publ_section_title
;
 One dimensional halogen bond design: Br&#x22EF;N versus I&#x22EF;N with
 fluoroarenes
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6098
_journal_page_last               6106
_journal_paper_doi               10.1039/D1CE00864A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C6 F4 I2, C7 H10 N2'
_chemical_formula_sum            'C13 H10 F4 I2 N2'
_chemical_formula_weight         524.040
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.062(1)
_cell_angle_beta                 95.417(1)
_cell_angle_gamma                110.587(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7759(2)
_cell_length_b                   9.1295(2)
_cell_length_c                   11.6480(1)
_cell_measurement_reflns_used    29132
_cell_measurement_temperature    106(8)
_cell_measurement_theta_max      29.1090
_cell_measurement_theta_min      1.7690
_cell_volume                     759.74(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9984
_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    -18.00  89.00   0.50    0.55    --   14.30  13.00  54.00  214
  2  \w      2.00  83.00   0.50    0.55    --   14.30  30.00 -90.00  162
  3  \w      2.00  83.00   0.50    0.55    --   14.30  30.00-180.00  162
  4  \w     -3.00  82.00   0.50    0.55    --   14.30  45.00 -90.00  170
  5  \w     -8.00  82.00   0.50    0.55    --   14.30  61.00  60.00  180
  6  \w    -13.00  83.00   0.50    0.55    --   14.30  77.00-150.00  192
  7  \w    -28.00  53.00   0.50    0.55    --  -15.63  30.00-150.00  162
  8  \w    -33.00  52.00   0.50    0.55    --  -15.63  45.00 -60.00  170
  9  \w    -45.00  59.00   0.50    0.55    --  -15.63  13.00  54.00  208
 10  \w      9.00  65.00   0.50    0.55    --   14.30-125.00 -90.00  112
 11  \w      9.00  65.00   0.50    0.55    --   14.30-125.00-180.00  112
 12  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00-150.00  110
 13  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00 -90.00  110
 14  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00 -60.00  110
 15  \w      9.00  65.00   0.50    0.55    --   14.30-125.00  60.00  112
 16  \w      9.00  65.00   0.50    0.55    --   14.30-125.00 150.00  112
 17  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00 120.00  110
 18  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00  90.00  110
 19  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00 -30.00  110
 20  \w    -38.00  17.00   0.50    0.55    --  -15.63 -94.00  60.00  110
 21  \w    -53.00  37.00   0.50    0.55    --   14.30 -61.00 150.00  180
 22  \w    -53.00  29.00   0.50    0.55    --   14.30 -45.00  30.00  164
 23  \w    -54.00  14.00   0.50    0.55    --   14.30 -30.00-120.00  136
 24  \w    -54.00  14.00   0.50    0.55    --   14.30 -30.00-150.00  136
 25  \w    -54.00  14.00   0.50    0.55    --   14.30 -30.00-180.00  136
 26  \w    -61.00   2.00   0.50    0.55    --   14.30 -13.00-117.00  126
 27  \w    -54.00  14.00   0.50    0.55    --   14.30 -30.00 -30.00  136
 28  \w    -60.00   3.00   0.50    0.55    --   14.30 -15.00  60.00  126
 29  \w    -53.00  29.00   0.50    0.55    --   14.30 -45.00 120.00  164
 30  \w    -60.00   3.00   0.50    0.55    --   14.30 -15.00 -60.00  126
 31  \w    -62.00  90.00   0.50    0.55    --   14.30   0.00-180.00  304
 32  \w    -60.00   3.00   0.50    0.55    --   14.30 -15.00 -30.00  126
 33  \w    -82.00   2.00   0.50    0.55    --  -15.63 -45.00 120.00  168
 34  \w    -82.00   2.00   0.50    0.55    --  -15.63 -45.00  30.00  168
 35  \w    -82.00   2.00   0.50    0.55    --  -15.63 -45.00-120.00  168
 36  \w    -83.00   7.00   0.50    0.55    --  -15.63 -61.00-180.00  180
 37  \w    -83.00   7.00   0.50    0.55    --  -15.63 -61.00   0.00  180
 38  \w    -84.00  -3.00   0.50    0.55    --  -15.63 -30.00-120.00  162
 39  \w    -82.00   2.00   0.50    0.55    --  -15.63 -45.00 -90.00  168
 40  \w    -82.00   2.00   0.50    0.55    --  -15.63 -45.00  60.00  168
 41  \w    -90.00   2.00   0.50    0.55    --  -15.63 -13.00-117.00  184
 42  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00 -60.00  114
 43  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00-150.00  114
 44  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00-120.00  114
 45  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00   0.00  114
 46  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00  60.00  114
 47  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00 120.00  114
 48  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00 150.00  114
 49  \w    -78.00 -19.00   0.50    0.55    --  -15.63 143.00  23.12  118
 50  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00 -30.00  114
 51  \w    -76.00 -17.00   0.50    0.55    --  -15.63 140.00-108.95  118
 52  \w    -66.00  -9.00   0.50    0.55    --  -15.63 125.00-180.00  114
 53  \w    -78.00 -19.00   0.50    0.55    --  -15.63 143.00 -85.75  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0688070000
_diffrn_orient_matrix_UB_12      0.0334175000
_diffrn_orient_matrix_UB_13      -0.0093233000
_diffrn_orient_matrix_UB_21      -0.0697270000
_diffrn_orient_matrix_UB_22      -0.0727842000
_diffrn_orient_matrix_UB_23      0.0054643000
_diffrn_orient_matrix_UB_31      0.0105594000
_diffrn_orient_matrix_UB_32      0.0259324000
_diffrn_orient_matrix_UB_33      0.0610964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            53237
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9984
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.78
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.175
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
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_density_diffrn    2.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             486.693
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.153
_refine_diff_density_max         1.4394
_refine_diff_density_min         -1.4836
_refine_diff_density_rms         0.1904
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             11.4321
_refine_ls_goodness_of_fit_ref   1.2580
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2580
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.3949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2819
_reflns_number_total             3146
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           I2F4bz_235Me3pyrz
_cod_depositor_comments
'Adding full bibliography for 7243307--7243335.cif.'
_cod_database_code               7243334
_chemical_oxdiff_formula         (I2F4C6)(N2C7H10)
_chemical_oxdiff_usercomment     (Br2F4Bz)(Me3pyrz)
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C10(H10)
1.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.627