#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243328.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_7243328
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, 2(C6 H4 N)'
_chemical_formula_sum            'C24 H8 F8 I2 N2'
_chemical_formula_weight         730.141
_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                113.307(3)
_cell_angle_beta                 99.272(3)
_cell_angle_gamma                94.932(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7139(6)
_cell_length_b                   12.2385(10)
_cell_length_c                   13.5005(11)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      30.064
_cell_measurement_theta_min      2.712
_cell_volume                     1139.37(16)
_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      100.01
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9979
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.9976
_diffrn_reflns_Laue_measured_fraction_max 0.9979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33909
_diffrn_reflns_point_group_measured_fraction_full 0.9976
_diffrn_reflns_point_group_measured_fraction_max 0.9979
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'fine focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.842
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9248.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             686.890
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.125
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.3912
_refine_diff_density_min         -0.3641
_refine_diff_density_rms         0.0710
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             7.5085
_refine_ls_goodness_of_fit_ref   1.0633
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0633
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0143
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0110P)²+1.0645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0355
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4343
_reflns_number_total             4656
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           I2F8bph_phenaz
_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               7243328
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_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 0.689356(16) 0.764198(11) 1.183744(10) 0.01766(4) Uani 1.000000 .
I2 I -0.155697(15) 0.211894(11) 0.329172(9) 0.01539(4) Uani 1.000000 .
F1 F 0.76982(14) 0.56544(11) 0.96283(10) 0.0243(3) Uani 1.000000 .
F2 F 0.57517(14) 0.44663(11) 0.75847(9) 0.0215(2) Uani 1.000000 .
F3 F 0.10133(15) 0.65343(11) 0.86570(9) 0.0240(3) Uani 1.000000 .
F4 F 0.29658(16) 0.77527(11) 1.06928(9) 0.0273(3) Uani 1.000000 .
F5 F 0.22279(16) 0.38656(12) 0.40596(9) 0.0268(3) Uani 1.000000 .
F6 F 0.42448(15) 0.52667(11) 0.60492(9) 0.0243(3) Uani 1.000000 .
F7 F -0.00892(14) 0.41265(11) 0.77194(9) 0.0210(2) Uani 1.000000 .
F8 F -0.21323(14) 0.27759(11) 0.57411(9) 0.0217(3) Uani 1.000000 .
C1 C 0.5383(3) 0.67321(17) 1.02274(15) 0.0166(4) Uani 1.000000 .
C2 C 0.6046(2) 0.58950(18) 0.94043(16) 0.0171(4) Uani 1.000000 .
C3 C 0.5043(2) 0.52746(17) 0.83438(15) 0.0159(4) Uani 1.000000 .
C4 C 0.3308(2) 0.54511(17) 0.80573(15) 0.0154(4) Uani 1.000000 .
C5 C 0.2669(3) 0.63023(18) 0.88856(16) 0.0177(4) Uani 1.000000 .
C6 C 0.3679(3) 0.69314(18) 0.99404(16) 0.0187(4) Uani 1.000000 .
C7 C -0.0003(2) 0.32668(17) 0.48429(15) 0.0156(4) Uani 1.000000 .
C8 C 0.1637(3) 0.39214(18) 0.49570(16) 0.0172(4) Uani 1.000000 .
C9 C 0.2684(2) 0.46371(18) 0.59841(16) 0.0173(4) Uani 1.000000 .
C10 C 0.2162(2) 0.47272(17) 0.69486(15) 0.0146(4) Uani 1.000000 .
C11 C 0.0502(2) 0.40872(18) 0.68269(15) 0.0155(4) Uani 1.000000 .
C12 C -0.0554(2) 0.33849(17) 0.57993(16) 0.0154(4) Uani 1.000000 .
N1 N 0.9176(2) 0.89752(15) 1.40223(13) 0.0167(3) Uani 1.000000 .
C13 C 0.8426(2) 0.93450(18) 1.49081(16) 0.0165(4) Uani 1.000000 .
C14 C 1.0743(2) 0.96133(17) 1.40991(16) 0.0158(4) Uani 1.000000 .
C15 C 1.1606(3) 0.92537(19) 1.31905(17) 0.0210(4) Uani 1.000000 .
H15 H 1.1083(3) 0.85587(19) 1.25329(17) 0.0252(5) Uiso 1.000000 R
C16 C 1.3183(3) 0.9906(2) 1.32639(17) 0.0235(4) Uani 1.000000 .
H16 H 1.3749(3) 0.9662(2) 1.26536(17) 0.0282(5) Uiso 1.000000 R
C17 C 1.3992(3) 1.0948(2) 1.42423(17) 0.0243(5) Uani 1.000000 .
H17 H 1.5085(3) 1.1396(2) 1.42738(17) 0.0292(5) Uiso 1.000000 R
C18 C 1.3222(3) 1.13120(19) 1.51316(17) 0.0211(4) Uani 1.000000 .
H18 H 1.3783(3) 1.20054(19) 1.57815(17) 0.0253(5) Uiso 1.000000 R
N2 N -0.3944(2) 0.06020(14) 0.10862(13) 0.0147(3) Uani 1.000000 .
C19 C -0.5562(2) 0.08650(17) 0.08209(15) 0.0144(4) Uani 1.000000 .
C20 C -0.6239(3) 0.17650(18) 0.16409(16) 0.0175(4) Uani 1.000000 .
H20 H -0.5558(3) 0.21650(18) 0.23752(16) 0.0210(5) Uiso 1.000000 R
C21 C -0.7862(3) 0.20511(18) 0.13718(16) 0.0192(4) Uani 1.000000 .
H21 H -0.8300(3) 0.26579(18) 0.19203(16) 0.0230(5) Uiso 1.000000 R
C22 C -0.3371(2) -0.02562(17) 0.02815(15) 0.0137(4) Uani 1.000000 .
C23 C -0.1677(2) -0.05780(18) 0.05210(16) 0.0167(4) Uani 1.000000 .
H23 H -0.0953(2) -0.01795(18) 0.12437(16) 0.0201(5) Uiso 1.000000 R
C24 C -0.1088(3) -0.14535(18) -0.02797(16) 0.0189(4) Uani 1.000000 .
H24 H 0.0040(3) -0.16691(18) -0.01078(16) 0.0226(5) 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
C2 C1 I1 121.36(14) . . ?
C6 C1 I1 121.51(14) . . ?
C6 C1 C2 117.13(17) . . ?
C1 C2 F1 120.23(17) . . ?
C3 C2 F1 118.10(17) . . ?
C3 C2 C1 121.67(17) . . ?
C2 C3 F2 118.93(17) . . ?
C4 C3 F2 119.65(16) . . ?
C4 C3 C2 121.40(17) . . ?
C5 C4 C3 116.32(17) . . ?
C10 C4 C3 122.22(17) . . ?
C10 C4 C5 121.38(17) . . ?
C4 C5 F3 119.32(16) . . ?
C6 C5 F3 118.49(17) . . ?
C6 C5 C4 122.19(18) . . ?
C1 C6 F4 120.30(17) . . ?
C5 C6 F4 118.44(17) . . ?
C5 C6 C1 121.27(18) . . ?
C8 C7 I2 121.63(14) . . ?
C12 C7 I2 121.06(14) . . ?
C12 C7 C8 117.30(17) . . ?
C7 C8 F5 120.12(17) . . ?
C9 C8 F5 118.72(17) . . ?
C9 C8 C7 121.16(17) . . ?
C8 C9 F6 118.80(17) . . ?
C10 C9 F6 119.45(16) . . ?
C10 C9 C8 121.75(17) . . ?
C9 C10 C4 122.37(17) . . ?
C11 C10 C4 120.94(17) . . ?
C11 C10 C9 116.69(17) . . ?
C10 C11 F7 120.11(16) . . ?
C12 C11 F7 118.41(16) . . ?
C12 C11 C10 121.47(17) . . ?
C7 C12 F8 120.00(16) . . ?
C11 C12 F8 118.38(17) . . ?
C11 C12 C7 121.59(17) . . ?
C14 N1 C13 117.67(16) . . ?
C14 C13 N1 121.37(17) 2_778 . ?
C18 C13 N1 119.58(17) 2_778 . ?
C18 C13 C14 119.04(18) 2_778 2_778 ?
C13 C14 N1 120.96(17) 2_778 . ?
C15 C14 N1 120.02(17) . . ?
C15 C14 C13 119.02(17) . 2_778 ?
H15 C15 C14 119.99(11) . . ?
C16 C15 C14 120.03(19) . . ?
C16 C15 H15 119.99(12) . . ?
H16 C16 C15 119.55(12) . . ?
C17 C16 C15 120.90(19) . . ?
C17 C16 H16 119.55(12) . . ?
H17 C17 C16 119.57(12) . . ?
C18 C17 C16 120.85(19) . . ?
C18 C17 H17 119.57(12) . . ?
C17 C18 C13 120.14(19) . 2_778 ?
H18 C18 C13 119.93(11) . 2_778 ?
H18 C18 C17 119.93(12) . . ?
C22 N2 C19 117.27(16) . . ?
C20 C19 N2 119.74(17) . . ?
C22 C19 N2 121.16(17) 2_455 . ?
C22 C19 C20 119.09(17) 2_455 . ?
H20 C20 C19 120.01(11) . . ?
C21 C20 C19 119.99(18) . . ?
C21 C20 H20 120.01(12) . . ?
H21 C21 C20 119.56(12) . . ?
C24 C21 C20 120.88(18) 2_455 . ?
C24 C21 H21 119.56(11) 2_455 . ?
C19 C22 N2 121.56(17) 2_455 . ?
C23 C22 N2 119.55(17) . . ?
C23 C22 C19 118.89(17) . 2_455 ?
H23 C23 C22 119.86(11) . . ?
C24 C23 C22 120.29(18) . . ?
C24 C23 H23 119.86(11) . . ?
C23 C24 C21 120.85(18) . 2_455 ?
H24 C24 C21 119.58(11) . 2_455 ?
H24 C24 C23 119.58(11) . . ?
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 2.0900(18) . ?
I2 C7 2.0904(18) . ?
F1 C2 1.347(2) . ?
F2 C3 1.341(2) . ?
F3 C5 1.346(2) . ?
F4 C6 1.346(2) . ?
F5 C8 1.341(2) . ?
F6 C9 1.343(2) . ?
F7 C11 1.341(2) . ?
F8 C12 1.346(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.387(3) . ?
C4 C10 1.482(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.382(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.378(3) . ?
N1 C13 1.345(2) . ?
N1 C14 1.348(2) . ?
C13 C14 1.436(3) 2_778 ?
C13 C18 1.426(3) 2_778 ?
C14 C15 1.424(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.363(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.423(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.358(3) . ?
C18 H18 0.9500 . ?
N2 C19 1.344(2) . ?
N2 C22 1.345(2) . ?
C19 C20 1.426(3) . ?
C19 C22 1.439(3) 2_455 ?
C20 H20 0.9500 . ?
C20 C21 1.361(3) . ?
C21 H21 0.9500 . ?
C21 C24 1.423(3) 2_455 ?
C22 C23 1.422(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.360(3) . ?
C24 H24 0.9500 . ?
