#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243313.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_7243313
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, C10 H8 N2'
_chemical_formula_sum            'C22 H8 F8 I2 N2'
_chemical_formula_weight         706.118
_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                105.190(4)
_cell_angle_beta                 107.580(2)
_cell_angle_gamma                90.334(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9217(5)
_cell_length_b                   11.1526(9)
_cell_length_c                   12.8382(10)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.19
_cell_volume                     1039.01(14)
_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 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            61424
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9995
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  0.745429
_exptl_absorpt_correction_T_min  0.648507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 61424 reflections, Rint = 0.0621
 (33545 with I > 3sig(I), Rint = 0.0505)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             662.879
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.6827
_refine_diff_density_min         -1.3693
_refine_diff_density_rms         0.3256
_refine_ls_d_res_high            0.7894
_refine_ls_d_res_low             9.3065
_refine_ls_goodness_of_fit_ref   1.0647
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0647
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+18.9701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3740
_reflns_number_total             4423
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           I2F8bph_44bipy
_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               7243313
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C21(H21), C19(H19), C17(H17), C14(H14), C22(H22), C18(H18), C13(H13)
;
_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 0.63130(6) 0.38542(4) 0.26393(4) 0.01490(11) Uani 1.000000 .
I2 I 1.11438(5) 0.86079(4) 1.21492(4) 0.01547(11) Uani 1.000000 .
F7 F 1.0396(5) 0.8272(3) 0.7750(3) 0.0185(8) Uani 1.000000 .
F2 F 0.6663(5) 0.7572(3) 0.6397(3) 0.0174(8) Uani 1.000000 .
F5 F 0.8805(5) 0.6006(4) 1.0643(3) 0.0186(8) Uani 1.000000 .
F3 F 1.0004(5) 0.4182(3) 0.7008(3) 0.0183(8) Uani 1.000000 .
F4 F 0.8974(5) 0.3108(3) 0.4787(3) 0.0179(8) Uani 1.000000 .
F6 F 0.7721(5) 0.4874(3) 0.8430(3) 0.0185(8) Uani 1.000000 .
F8 F 1.1596(5) 0.9378(3) 0.9973(3) 0.0190(8) Uani 1.000000 .
F1 F 0.5437(5) 0.6418(4) 0.4175(3) 0.0195(8) Uani 1.000000 .
N1 N 0.5169(8) 0.2727(5) 0.0351(5) 0.0197(12) Uani 1.000000 .
N2 N 0.2221(7) -0.0262(5) -0.5547(5) 0.0186(12) Uani 1.000000 .
C7 C 1.0246(9) 0.7729(6) 1.0389(6) 0.0153(13) Uani 1.000000 .
C5 C 0.8911(8) 0.4760(6) 0.6326(5) 0.0130(12) Uani 1.000000 .
C8 C 0.9250(8) 0.6577(6) 0.9953(6) 0.0164(13) Uani 1.000000 .
C20 C 0.3292(9) 0.0918(6) -0.3210(6) 0.0162(13) Uani 1.000000 .
C15 C 0.3924(8) 0.1556(6) -0.1976(5) 0.0124(12) Uani 1.000000 .
C6 C 0.8334(8) 0.4195(6) 0.5156(6) 0.0135(13) Uani 1.000000 .
C2 C 0.6618(8) 0.5872(6) 0.4862(5) 0.0133(12) Uani 1.000000 .
C16 C 0.3718(9) 0.0949(6) -0.1190(6) 0.0174(13) Uani 1.000000 .
H16 H 0.3166(9) 0.0121(6) -0.1441(6) 0.0209(16) Uiso 1.000000 R
C11 C 0.9987(9) 0.7699(6) 0.8455(6) 0.0152(13) Uani 1.000000 .
C21 C 0.3838(9) -0.0256(6) -0.3645(6) 0.0189(14) Uani 1.000000 .
H21 H 0.4579(9) -0.0675(6) -0.3148(6) 0.0227(17) Uiso 1.000000 R
C9 C 0.8666(8) 0.5991(6) 0.8792(6) 0.0150(13) Uani 1.000000 .
C10 C 0.9019(8) 0.6543(6) 0.8025(6) 0.0143(13) Uani 1.000000 .
C4 C 0.8383(8) 0.5916(6) 0.6782(5) 0.0127(12) Uani 1.000000 .
C3 C 0.7229(9) 0.6462(6) 0.6020(6) 0.0175(14) Uani 1.000000 .
C12 C 1.0613(8) 0.8273(6) 0.9615(6) 0.0156(13) Uani 1.000000 .
C19 C 0.2191(9) 0.1474(6) -0.3983(6) 0.0181(14) Uani 1.000000 .
H19 H 0.1799(9) 0.2269(6) -0.3728(6) 0.0217(16) Uiso 1.000000 R
C17 C 0.4326(9) 0.1569(6) -0.0049(6) 0.0194(14) Uani 1.000000 .
H17 H 0.4144(9) 0.1163(6) 0.0478(6) 0.0233(17) Uiso 1.000000 R
C1 C 0.7179(8) 0.4736(6) 0.4408(6) 0.0156(13) Uani 1.000000 .
C14 C 0.4756(9) 0.2758(6) -0.1569(6) 0.0192(14) Uani 1.000000 .
H14 H 0.4908(9) 0.3205(6) -0.2076(6) 0.0231(17) Uiso 1.000000 R
C22 C 0.3278(9) -0.0788(7) -0.4805(6) 0.0212(15) Uani 1.000000 .
H22 H 0.3669(9) -0.1574(7) -0.5090(6) 0.0255(17) Uiso 1.000000 R
C18 C 0.1677(9) 0.0849(6) -0.5131(6) 0.0207(14) Uani 1.000000 .
H18 H 0.0899(9) 0.1225(6) -0.5651(6) 0.0248(17) Uiso 1.000000 R
C13 C 0.5370(9) 0.3300(7) -0.0389(6) 0.0208(14) Uani 1.000000 .
H13 H 0.5958(9) 0.4119(7) -0.0109(6) 0.0250(17) 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
C13 N1 C17 118.3(6) . . ?
C18 N2 C22 117.4(6) . . ?
C8 C7 I2 121.2(5) . . ?
C12 C7 I2 121.7(5) . . ?
C12 C7 C8 117.1(6) . . ?
C6 C5 F3 118.9(5) . . ?
C4 C5 F3 120.0(6) . . ?
C4 C5 C6 121.1(6) . . ?
C7 C8 F5 120.7(6) . . ?
C9 C8 F5 118.0(6) . . ?
C9 C8 C7 121.3(6) . . ?
C21 C20 C15 121.0(6) . . ?
C19 C20 C15 121.3(6) . . ?
C19 C20 C21 117.7(6) . . ?
C16 C15 C20 120.7(6) . . ?
C14 C15 C20 121.0(6) . . ?
C14 C15 C16 118.3(6) . . ?
C5 C6 F4 117.1(6) . . ?
C1 C6 F4 121.3(6) . . ?
C1 C6 C5 121.6(6) . . ?
C3 C2 F1 118.7(6) . . ?
C1 C2 F1 119.8(6) . . ?
C1 C2 C3 121.5(6) . . ?
H16 C16 C15 120.5(4) . . ?
C17 C16 C15 119.1(6) . . ?
C17 C16 H16 120.5(4) . . ?
C10 C11 F7 120.1(6) . . ?
C12 C11 F7 118.5(6) . . ?
C12 C11 C10 121.3(6) . . ?
H21 C21 C20 120.6(4) . . ?
C22 C21 C20 118.8(6) . . ?
C22 C21 H21 120.6(4) . . ?
C8 C9 F6 118.1(6) . . ?
C10 C9 F6 120.5(6) . . ?
C10 C9 C8 121.3(6) . . ?
C9 C10 C11 117.5(6) . . ?
C4 C10 C11 121.2(6) . . ?
C4 C10 C9 121.2(5) . . ?
C10 C4 C5 121.7(5) . . ?
C3 C4 C5 117.0(6) . . ?
C3 C4 C10 121.4(6) . . ?
C2 C3 F2 118.3(6) . . ?
C4 C3 F2 120.3(6) . . ?
C4 C3 C2 121.5(6) . . ?
C7 C12 F8 120.7(6) . . ?
C11 C12 F8 118.0(6) . . ?
C11 C12 C7 121.3(6) . . ?
H19 C19 C20 120.6(4) . . ?
C18 C19 C20 118.9(6) . . ?
C18 C19 H19 120.6(4) . . ?
C16 C17 N1 122.7(6) . . ?
H17 C17 N1 118.6(4) . . ?
H17 C17 C16 118.6(4) . . ?
C6 C1 I1 120.9(5) . . ?
C2 C1 I1 121.8(5) . . ?
C2 C1 C6 117.3(6) . . ?
H14 C14 C15 120.8(4) . . ?
C13 C14 C15 118.4(7) . . ?
C13 C14 H14 120.8(4) . . ?
C21 C22 N2 123.7(6) . . ?
H22 C22 N2 118.1(4) . . ?
H22 C22 C21 118.1(4) . . ?
C19 C18 N2 123.4(7) . . ?
H18 C18 N2 118.3(4) . . ?
H18 C18 C19 118.3(4) . . ?
C14 C13 N1 123.2(7) . . ?
H13 C13 N1 118.4(4) . . ?
H13 C13 C14 118.4(4) . . ?
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 C1 2.115(7) . ?
I2 C7 2.106(7) . ?
F7 C11 1.346(7) . ?
F2 C3 1.338(7) . ?
F5 C8 1.340(7) . ?
F3 C5 1.333(7) . ?
F4 C6 1.342(7) . ?
F6 C9 1.343(7) . ?
F8 C12 1.347(7) . ?
F1 C2 1.347(7) . ?
N1 C17 1.346(9) . ?
N1 C13 1.321(9) . ?
N2 C22 1.330(9) . ?
N2 C18 1.343(9) . ?
C7 C8 1.389(9) . ?
C7 C12 1.389(9) . ?
C5 C6 1.396(9) . ?
C5 C4 1.393(9) . ?
C8 C9 1.390(9) . ?
C20 C15 1.480(8) . ?
C20 C21 1.409(9) . ?
C20 C19 1.391(9) . ?
C15 C16 1.399(9) . ?
C15 C14 1.386(9) . ?
C6 C1 1.380(9) . ?
C2 C3 1.388(9) . ?
C2 C1 1.385(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(10) . ?
C11 C10 1.384(9) . ?
C11 C12 1.387(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(10) . ?
C9 C10 1.382(9) . ?
C10 C4 1.488(8) . ?
C4 C3 1.393(9) . ?
C19 H19 0.9500 . ?
C19 C18 1.386(10) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.402(10) . ?
C22 H22 0.9500 . ?
C18 H18 0.9500 . ?
C13 H13 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 C1 C6 F4 1.4(6) . . . . ?
I1 C1 C6 C5 -179.6(5) . . . . ?
I1 C1 C2 F1 2.5(6) . . . . ?
I1 C1 C2 C3 -178.2(5) . . . . ?
I2 C7 C8 F5 1.3(5) . . . . ?
I2 C7 C8 C9 -179.5(5) . . . . ?
I2 C7 C12 F8 1.4(6) . . . . ?
I2 C7 C12 C11 -178.7(5) . . . . ?
F7 C11 C10 C9 178.9(6) . . . . ?
F7 C11 C10 C4 -1.1(7) . . . . ?
F7 C11 C12 F8 0.2(6) . . . . ?
F7 C11 C12 C7 -179.7(5) . . . . ?
F2 C3 C2 F1 -2.4(7) . . . . ?
F2 C3 C2 C1 178.4(6) . . . . ?
F2 C3 C4 C5 179.9(6) . . . . ?
F2 C3 C4 C10 0.0(7) . . . . ?
F5 C8 C7 C12 -178.4(6) . . . . ?
F5 C8 C9 F6 -1.3(6) . . . . ?
F5 C8 C9 C10 177.7(5) . . . . ?
F3 C5 C6 F4 -2.1(6) . . . . ?
F3 C5 C6 C1 178.9(5) . . . . ?
F3 C5 C4 C10 0.5(7) . . . . ?
F3 C5 C4 C3 -179.5(6) . . . . ?
F4 C6 C5 C4 177.0(5) . . . . ?
F4 C6 C1 C2 -178.6(6) . . . . ?
F6 C9 C8 C7 179.5(5) . . . . ?
F6 C9 C10 C11 179.4(6) . . . . ?
F6 C9 C10 C4 -0.6(7) . . . . ?
F8 C12 C7 C8 -178.9(6) . . . . ?
F8 C12 C11 C10 177.8(5) . . . . ?
F1 C2 C3 C4 176.9(5) . . . . ?
F1 C2 C1 C6 -177.4(6) . . . . ?
N1 C17 C16 C15 -2.2(8) . . . . ?
N1 C13 C14 C15 -1.0(8) . . . . ?
N2 C22 C21 C20 -0.9(8) . . . . ?
N2 C18 C19 C20 -1.7(8) . . . . ?
C7 C8 C9 C10 -1.5(8) . . . . ?
C7 C12 C11 C10 -2.0(7) . . . . ?
C5 C6 C1 C2 0.4(7) . . . . ?
C5 C4 C10 C11 119.4(6) . . . . ?
C5 C4 C10 C9 -60.6(7) . . . . ?
C5 C4 C3 C2 0.7(7) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C8 C9 C10 C4 -179.6(6) . . . . ?
C20 C15 C16 C17 179.8(6) . . . . ?
C20 C15 C14 C13 -178.2(6) . . . . ?
C6 C1 C2 C3 1.8(8) . . . . ?
C2 C3 C4 C10 -179.2(6) . . . . ?
C11 C10 C4 C3 -60.7(7) . . . . ?
C9 C10 C4 C3 119.4(6) . . . . ?
