#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243324.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7243324
loop_
_publ_author_name
'Peloquin, Andrew J.'
'McMillen, Colin D.'
'Pennington, William T.'
_publ_section_title
;
 One dimensional halogen bond design: Br⋯N versus I⋯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         'C12 F8 I2, C12 H10 N2'
_chemical_formula_sum            'C24 H10 F8 I2 N2'
_chemical_formula_weight         732.156
_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
_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                108.756(2)
_cell_angle_beta                 105.483(2)
_cell_angle_gamma                90.273(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9651(5)
_cell_length_b                   10.8942(7)
_cell_length_c                   14.4024(10)
_cell_measurement_reflns_used    30125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.67
_cell_volume                     1134.80(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36775
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9991
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.67
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    2.854
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1225 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.8986.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             690.890
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.7799
_refine_diff_density_min         -0.9158
_refine_diff_density_rms         0.1316
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             7.6381
_refine_ls_goodness_of_fit_ref   1.0903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0903
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0236
_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/[σ²(Fo²)+(0.0110P)²+4.4227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0580
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4103
_reflns_number_total             4686
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           I2F8bph_dpe
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243307--7243335.cif.
;
_cod_database_code               7243324
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
I1 I 1.07401(3) 0.84705(2) 1.166030(17) 0.01764(6) Uani 1.000000 .
I2 I 0.64750(3) 0.38941(2) 0.300070(17) 0.01865(6) Uani 1.000000 .
F1 F 0.8838(3) 0.6541(2) 0.45448(16) 0.0224(4) Uani 1.000000 .
F2 F 0.9748(3) 0.76370(19) 0.65806(16) 0.0203(4) Uani 1.000000 .
F3 F 0.6849(3) 0.40163(19) 0.68306(15) 0.0206(4) Uani 1.000000 .
F4 F 0.5694(3) 0.30218(19) 0.47938(16) 0.0214(4) Uani 1.000000 .
F5 F 0.7329(3) 0.82855(19) 0.78242(15) 0.0201(4) Uani 1.000000 .
F6 F 0.8301(3) 0.93616(19) 0.98562(16) 0.0210(4) Uani 1.000000 .
F7 F 1.1560(3) 0.5806(2) 1.01237(16) 0.0211(4) Uani 1.000000 .
F8 F 1.0515(3) 0.47087(19) 0.80886(16) 0.0214(4) Uani 1.000000 .
C13 C 0.7261(4) 0.4732(3) 0.4599(3) 0.0153(7) Uani 1.000000 .
C14 C 0.8288(4) 0.5913(3) 0.5095(3) 0.0165(7) Uani 1.000000 .
C15 C 0.8780(4) 0.6475(3) 0.6144(3) 0.0160(7) Uani 1.000000 .
C16 C 0.8329(4) 0.5858(3) 0.6769(3) 0.0159(7) Uani 1.000000 .
C17 C 0.7329(4) 0.4664(3) 0.6274(3) 0.0177(7) Uani 1.000000 .
C18 C 0.6775(4) 0.4144(3) 0.5227(3) 0.0173(7) Uani 1.000000 .
C19 C 0.8887(4) 0.6462(3) 0.7899(3) 0.0152(7) Uani 1.000000 .
C20 C 0.8385(4) 0.7662(3) 0.8388(3) 0.0155(7) Uani 1.000000 .
C21 C 0.8891(4) 0.8214(3) 0.9432(3) 0.0161(7) Uani 1.000000 .
C22 C 0.9959(4) 0.7621(3) 1.0055(3) 0.0164(7) Uani 1.000000 .
C23 C 1.0490(4) 0.6430(3) 0.9566(3) 0.0171(7) Uani 1.000000 .
C24 C 0.9960(4) 0.5863(3) 0.8520(3) 0.0169(7) Uani 1.000000 .
N1 N 0.1772(4) -0.0536(3) -0.6250(2) 0.0184(6) Uani 1.000000 .
N2 N 0.5394(4) 0.2878(3) 0.0931(2) 0.0195(6) Uani 1.000000 .
C1 C 0.3819(5) 0.1780(4) -0.2335(3) 0.0195(7) Uani 1.000000 .
H1 H 0.3715(5) 0.2467(4) -0.2613(3) 0.0234(9) Uiso 1.000000 R
C2 C 0.3457(5) 0.0552(4) -0.2991(3) 0.0186(7) Uani 1.000000 .
H2 H 0.3576(5) -0.0136(4) -0.2714(3) 0.0224(9) Uiso 1.000000 R
C3 C 0.4365(4) 0.2132(3) -0.1214(3) 0.0164(7) Uani 1.000000 .
C4 C 0.3926(5) 0.3298(3) -0.0613(3) 0.0202(7) Uani 1.000000 .
H4 H 0.3278(5) 0.3863(3) -0.0924(3) 0.0243(9) Uiso 1.000000 R
C5 C 0.4444(5) 0.3624(4) 0.0439(3) 0.0213(7) Uani 1.000000 .
H5 H 0.4114(5) 0.4413(4) 0.0837(3) 0.0256(9) Uiso 1.000000 R
C6 C 0.5809(5) 0.1762(4) 0.0345(3) 0.0204(7) Uani 1.000000 .
H6 H 0.6472(5) 0.1220(4) 0.0674(3) 0.0245(9) Uiso 1.000000 R
C7 C 0.5329(5) 0.1353(3) -0.0712(3) 0.0191(7) Uani 1.000000 .
H7 H 0.5654(5) 0.0549(3) -0.1091(3) 0.0230(9) Uiso 1.000000 R
C8 C 0.2891(5) 0.0205(3) -0.4104(3) 0.0181(7) Uani 1.000000 .
C9 C 0.3394(5) 0.0964(3) -0.4622(3) 0.0194(7) Uani 1.000000 .
H9 H 0.4132(5) 0.1753(3) -0.4250(3) 0.0233(9) Uiso 1.000000 R
C10 C 0.2814(5) 0.0562(4) -0.5674(3) 0.0213(8) Uani 1.000000 .
H10 H 0.3174(5) 0.1093(4) -0.6010(3) 0.0256(9) Uiso 1.000000 R
C11 C 0.1283(5) -0.1269(3) -0.5759(3) 0.0210(7) Uani 1.000000 .
H11 H 0.0535(5) -0.2048(3) -0.6153(3) 0.0252(9) Uiso 1.000000 R
C12 C 0.1814(5) -0.0943(3) -0.4707(3) 0.0204(7) Uani 1.000000 .
H12 H 0.1447(5) -0.1501(3) -0.4394(3) 0.0244(9) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07119989395
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C13 I2 122.0(2) . . ?
C18 C13 I2 122.2(3) . . ?
C18 C13 C14 115.8(3) . . ?
C13 C14 F1 119.7(3) . . ?
C15 C14 F1 118.3(3) . . ?
C15 C14 C13 122.0(3) . . ?
C14 C15 F2 119.3(3) . . ?
C16 C15 F2 119.0(3) . . ?
C16 C15 C14 121.7(3) . . ?
C17 C16 C15 116.3(3) . . ?
C19 C16 C15 121.3(3) . . ?
C19 C16 C17 122.4(3) . . ?
C16 C17 F3 119.4(3) . . ?
C18 C17 F3 119.1(3) . . ?
C18 C17 C16 121.5(3) . . ?
C13 C18 F4 119.1(3) . . ?
C17 C18 F4 118.3(3) . . ?
C17 C18 C13 122.6(3) . . ?
C20 C19 C16 121.8(3) . . ?
C24 C19 C16 121.6(3) . . ?
C24 C19 C20 116.6(3) . . ?
C19 C20 F5 119.3(3) . . ?
C21 C20 F5 119.0(3) . . ?
C21 C20 C19 121.7(3) . . ?
C20 C21 F6 118.4(3) . . ?
C22 C21 F6 119.7(3) . . ?
C22 C21 C20 121.9(3) . . ?
C21 C22 I1 122.0(2) . . ?
C23 C22 I1 121.6(3) . . ?
C23 C22 C21 116.5(3) . . ?
C22 C23 F7 119.8(3) . . ?
C24 C23 F7 118.5(3) . . ?
C24 C23 C22 121.8(3) . . ?
C19 C24 F8 119.3(3) . . ?
C23 C24 F8 119.2(3) . . ?
C23 C24 C19 121.5(3) . . ?
C11 N1 C10 117.1(3) . . ?
C6 N2 C5 116.6(3) . . ?
C2 C1 H1 117.8(2) . . ?
C3 C1 H1 117.8(2) . . ?
C3 C1 C2 124.3(3) . . ?
H2 C2 C1 117.9(2) . . ?
C8 C2 C1 124.2(3) . . ?
C8 C2 H2 117.9(2) . . ?
C4 C3 C1 119.6(3) . . ?
C7 C3 C1 122.9(3) . . ?
C7 C3 C4 117.5(3) . . ?
H4 C4 C3 120.3(2) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3(2) . . ?
C4 C5 N2 123.4(3) . . ?
H5 C5 N2 118.3(2) . . ?
H5 C5 C4 118.3(2) . . ?
H6 C6 N2 118.1(2) . . ?
C7 C6 N2 123.9(3) . . ?
C7 C6 H6 118.1(2) . . ?
C6 C7 C3 119.3(3) . . ?
H7 C7 C3 120.4(2) . . ?
H7 C7 C6 120.4(2) . . ?
C9 C8 C2 123.3(3) . . ?
C12 C8 C2 120.1(3) . . ?
C12 C8 C9 116.5(3) . . ?
H9 C9 C8 120.2(2) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2(2) . . ?
C9 C10 N1 123.6(3) . . ?
H10 C10 N1 118.2(2) . . ?
H10 C10 C9 118.2(2) . . ?
H11 C11 N1 118.5(2) . . ?
C12 C11 N1 123.1(3) . . ?
C12 C11 H11 118.5(2) . . ?
C11 C12 C8 120.0(3) . . ?
H12 C12 C8 120.0(2) . . ?
H12 C12 C11 120.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C22 2.106(3) . ?
I2 C13 2.097(3) . ?
F1 C14 1.349(4) . ?
F2 C15 1.346(4) . ?
F3 C17 1.346(4) . ?
F4 C18 1.355(4) . ?
F5 C20 1.351(4) . ?
F6 C21 1.351(4) . ?
F7 C23 1.351(4) . ?
F8 C24 1.346(4) . ?
C13 C14 1.387(5) . ?
C13 C18 1.391(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.398(5) . ?
C16 C17 1.387(5) . ?
C16 C19 1.483(5) . ?
C17 C18 1.373(5) . ?
C19 C20 1.389(5) . ?
C19 C24 1.389(5) . ?
C20 C21 1.371(5) . ?
C21 C22 1.384(5) . ?
C22 C23 1.391(5) . ?
C23 C24 1.374(5) . ?
N1 C10 1.339(5) . ?
N1 C11 1.339(5) . ?
N2 C5 1.351(5) . ?
N2 C6 1.339(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.343(5) . ?
C1 C3 1.472(5) . ?
C2 H2 0.9500 . ?
C2 C8 1.463(5) . ?
C3 C4 1.394(5) . ?
C3 C7 1.392(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 C12 1.395(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.383(5) . ?
C12 H12 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C22 C21 F6 -1.0(3) . . . . ?
I1 C22 C21 C20 179.9(3) . . . . ?
I1 C22 C23 F7 -1.3(3) . . . . ?
I1 C22 C23 C24 178.9(3) . . . . ?
I2 C13 C14 F1 -1.3(3) . . . . ?
I2 C13 C14 C15 178.9(2) . . . . ?
I2 C13 C18 F4 -3.1(3) . . . . ?
I2 C13 C18 C17 177.9(3) . . . . ?
F1 C14 C13 C18 179.1(3) . . . . ?
F1 C14 C15 F2 1.6(3) . . . . ?
F1 C14 C15 C16 -177.1(3) . . . . ?
F2 C15 C14 C13 -178.6(3) . . . . ?
F2 C15 C16 C17 179.9(3) . . . . ?
F2 C15 C16 C19 0.3(4) . . . . ?
F3 C17 C16 C15 180.0(3) . . . . ?
F3 C17 C16 C19 -0.5(4) . . . . ?
F3 C17 C18 F4 3.0(3) . . . . ?
F3 C17 C18 C13 -177.9(3) . . . . ?
F4 C18 C13 C14 176.5(3) . . . . ?
F4 C18 C17 C16 -175.1(3) . . . . ?
F5 C20 C19 C16 1.5(4) . . . . ?
F5 C20 C19 C24 -179.4(3) . . . . ?
F5 C20 C21 F6 0.4(3) . . . . ?
F5 C20 C21 C22 179.4(3) . . . . ?
F6 C21 C20 C19 -177.6(3) . . . . ?
F6 C21 C22 C23 178.8(3) . . . . ?
F7 C23 C22 C21 178.8(3) . . . . ?
F7 C23 C24 F8 0.2(3) . . . . ?
F7 C23 C24 C19 -178.8(3) . . . . ?
F8 C24 C19 C16 0.3(4) . . . . ?
F8 C24 C19 C20 -178.8(3) . . . . ?
F8 C24 C23 C22 -180.0(3) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
C13 C18 C17 C16 3.9(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C14 C15 C16 C19 179.1(3) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C15 C16 C19 C20 60.6(4) . . . . ?
C15 C16 C19 C24 -118.5(3) . . . . ?
C16 C19 C20 C21 179.5(3) . . . . ?
C16 C19 C24 C23 179.3(3) . . . . ?
C19 C20 C21 C22 1.4(4) . . . . ?
C19 C24 C23 C22 1.0(4) . . . . ?
C20 C21 C22 C23 -0.2(4) . . . . ?
C21 C22 C23 C24 -1.0(4) . . . . ?
N1 C10 C9 C8 0.1(4) . . . . ?
N1 C11 C12 C8 0.9(4) . . . . ?
N2 C5 C4 C3 1.2(4) . . . . ?
N2 C6 C7 C3 0.4(4) . . . . ?
C1 C2 C8 C9 30.3(4) . . . . ?
C1 C2 C8 C12 -150.6(4) . . . . ?
C1 C3 C4 C5 -180.0(3) . . . . ?
C1 C3 C7 C6 179.2(3) . . . . ?
C2 C8 C9 C10 179.4(3) . . . . ?
C2 C8 C12 C11 -179.9(3) . . . . ?
