#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243333.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_7243333
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, C6 H8 N2'
_chemical_formula_sum            'C18 H8 F8 I2 N2'
_chemical_formula_weight         658.074
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6612(11)
_cell_length_b                   12.5742(12)
_cell_length_c                   12.2189(11)
_cell_measurement_reflns_used    9653
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.83
_cell_volume                     1945.3(3)
_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 0.9984
_diffrn_measured_fraction_theta_max 0.9989
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            64662
_diffrn_reflns_point_group_measured_fraction_full 0.9986
_diffrn_reflns_point_group_measured_fraction_max 0.9990
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.28
_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    3.315
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1050 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8161.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1229.716
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         3.1905
_refine_diff_density_min         -0.6353
_refine_diff_density_rms         0.1322
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.361(17)
_refine_ls_d_res_high            0.7400
_refine_ls_d_res_low             8.9219
_refine_ls_goodness_of_fit_ref   1.0488
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0488
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0265
_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)+(0.0404P)²+2.7848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                4915
_reflns_number_total             5019
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           I2F8bph_25Me2pyrz
_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_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7243333
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.639437
 0.360563
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_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+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,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 0.708329(18) 0.568024(17) 0.42775(2) 0.01813(6) Uani 1.000000 .
I2 I 0.735643(19) -0.285538(18) 0.72416(2) 0.01974(6) Uani 1.000000 .
F1 F 0.55486(18) 0.36556(18) 0.39560(19) 0.0214(5) Uani 1.000000 .
F2 F 0.56154(17) 0.16894(18) 0.47367(19) 0.0197(4) Uani 1.000000 .
F3 F 0.89308(18) 0.24009(19) 0.6354(2) 0.0211(5) Uani 1.000000 .
F4 F 0.8836(2) 0.44017(18) 0.5626(2) 0.0215(5) Uani 1.000000 .
F5 F 0.89935(19) -0.1460(2) 0.5825(2) 0.0237(5) Uani 1.000000 .
F6 F 0.89460(18) 0.05370(18) 0.5110(2) 0.0214(5) Uani 1.000000 .
F7 F 0.56944(17) 0.10781(18) 0.69339(18) 0.0184(4) Uani 1.000000 .
F8 F 0.57163(19) -0.0935(2) 0.7614(2) 0.0238(5) Uani 1.000000 .
C1 C 0.7181(3) 0.4094(3) 0.4783(3) 0.0152(7) Uani 1.000000 .
C2 C 0.6374(3) 0.3379(3) 0.4570(3) 0.0157(7) Uani 1.000000 .
C3 C 0.6416(3) 0.2349(3) 0.4974(3) 0.0144(6) Uani 1.000000 .
C4 C 0.7274(3) 0.1975(3) 0.5583(3) 0.0161(7) Uani 1.000000 .
C5 C 0.8089(3) 0.2699(3) 0.5765(3) 0.0164(7) Uani 1.000000 .
C6 C 0.8049(3) 0.3729(3) 0.5387(3) 0.0157(7) Uani 1.000000 .
C7 C 0.7345(3) -0.1264(3) 0.6733(3) 0.0177(7) Uani 1.000000 .
C8 C 0.8170(3) -0.0853(3) 0.6109(3) 0.0184(8) Uani 1.000000 .
C9 C 0.8147(3) 0.0186(3) 0.5739(3) 0.0160(7) Uani 1.000000 .
C10 C 0.7308(3) 0.0872(3) 0.5981(3) 0.0141(7) Uani 1.000000 .
C11 C 0.6500(3) 0.0449(3) 0.6622(3) 0.0141(6) Uani 1.000000 .
C12 C 0.6519(3) -0.0590(3) 0.6984(3) 0.0154(7) Uani 1.000000 .
N1 N 0.7164(3) 0.7899(3) 0.3690(3) 0.0239(8) Uani 1.000000 .
N2 N 0.7499(3) 0.9959(3) 0.2933(3) 0.0223(7) Uani 1.000000 .
C13 C 0.8063(3) 0.8196(3) 0.3201(4) 0.0238(8) Uani 1.000000 .
H13 H 0.8597(3) 0.7674(3) 0.3099(4) 0.0286(10) Uiso 1.000000 R
C14 C 0.8260(3) 0.9220(3) 0.2836(4) 0.0226(9) Uani 1.000000 .
C15 C 0.6591(3) 0.9663(3) 0.3406(4) 0.0218(8) Uani 1.000000 .
H15 H 0.6039(3) 1.0172(3) 0.3463(4) 0.0261(9) Uiso 1.000000 R
C16 C 0.6415(3) 0.8645(3) 0.3820(3) 0.0216(8) Uani 1.000000 .
C17 C 0.9283(3) 0.9542(3) 0.2335(4) 0.0262(8) Uani 1.000000 .
H17a H 0.9150(3) 1.002(2) 0.1720(19) 0.0393(12) Uiso 1.000000 GR
H17b H 0.9717(12) 0.991(3) 0.2884(9) 0.0393(12) Uiso 1.000000 GR
H17c H 0.9656(13) 0.8910(4) 0.207(3) 0.0393(12) Uiso 1.000000 GR
C18 C 0.5419(3) 0.8339(4) 0.4383(5) 0.0331(10) Uani 1.000000 .
H18a H 0.5169(17) 0.7657(16) 0.409(2) 0.0497(15) Uiso 1.000000 GR
H18b H 0.5549(8) 0.827(3) 0.5170(6) 0.0497(15) Uiso 1.000000 GR
H18c H 0.4882(10) 0.8886(16) 0.426(3) 0.0497(15) Uiso 1.000000 GR
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 121.3(3) . . ?
C6 C1 I1 121.0(3) . . ?
C6 C1 C2 117.7(3) . . ?
C1 C2 F1 120.9(3) . . ?
C3 C2 F1 118.3(3) . . ?
C3 C2 C1 120.7(3) . . ?
C2 C3 F2 118.1(3) . . ?
C4 C3 F2 119.6(3) . . ?
C4 C3 C2 122.2(3) . . ?
C5 C4 C3 116.2(4) . . ?
C10 C4 C3 121.0(3) . . ?
C10 C4 C5 122.8(3) . . ?
C4 C5 F3 119.5(4) . . ?
C6 C5 F3 118.3(3) . . ?
C6 C5 C4 122.2(3) . . ?
C1 C6 F4 119.4(3) . . ?
C5 C6 F4 119.5(3) . . ?
C5 C6 C1 121.0(3) . . ?
C8 C7 I2 120.8(3) . . ?
C12 C7 I2 121.7(3) . . ?
C12 C7 C8 117.5(4) . . ?
C7 C8 F5 120.9(4) . . ?
C9 C8 F5 118.1(4) . . ?
C9 C8 C7 120.9(4) . . ?
C8 C9 F6 118.7(3) . . ?
C10 C9 F6 119.3(3) . . ?
C10 C9 C8 122.0(4) . . ?
C9 C10 C4 122.2(3) . . ?
C11 C10 C4 121.6(3) . . ?
C11 C10 C9 116.2(4) . . ?
C10 C11 F7 119.4(3) . . ?
C12 C11 F7 118.7(3) . . ?
C12 C11 C10 121.9(3) . . ?
C7 C12 F8 120.1(3) . . ?
C11 C12 F8 118.3(3) . . ?
C11 C12 C7 121.6(3) . . ?
C16 N1 C13 117.3(4) . . ?
C15 N2 C14 117.5(4) . . ?
H13 C13 N1 118.1(2) . . ?
C14 C13 N1 123.8(4) . . ?
C14 C13 H13 118.1(3) . . ?
C13 C14 N2 119.1(4) . . ?
C17 C14 N2 118.1(4) . . ?
C17 C14 C13 122.8(4) . . ?
H15 C15 N2 118.4(2) . . ?
C16 C15 N2 123.2(4) . . ?
C16 C15 H15 118.4(2) . . ?
C15 C16 N1 119.1(4) . . ?
C18 C16 N1 118.3(4) . . ?
C18 C16 C15 122.7(4) . . ?
H17a C17 C14 109.5 . . ?
H17b C17 C14 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C14 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18a C18 C16 109.5 . . ?
H18b C18 C16 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C16 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
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 2.091(4) . ?
I2 C7 2.096(4) . ?
F1 C2 1.333(4) . ?
F2 C3 1.341(4) . ?
F3 C5 1.339(4) . ?
F4 C6 1.339(4) . ?
F5 C8 1.339(4) . ?
F6 C9 1.346(4) . ?
F7 C11 1.346(4) . ?
F8 C12 1.347(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.400(5) . ?
C2 C3 1.387(5) . ?
C3 C4 1.398(5) . ?
C4 C5 1.394(6) . ?
C4 C10 1.471(5) . ?
C5 C6 1.377(6) . ?
C7 C8 1.393(6) . ?
C7 C12 1.379(6) . ?
C8 C9 1.382(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.394(5) . ?
C11 C12 1.380(5) . ?
N1 C13 1.338(7) . ?
N1 C16 1.343(6) . ?
N2 C14 1.345(5) . ?
N2 C15 1.340(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(6) . ?
C14 C17 1.489(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(6) . ?
C16 C18 1.487(6) . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
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 C2 F1 5.7(3) . . . . ?
I1 C1 C2 C3 -175.5(3) . . . . ?
I1 C1 C6 F4 -1.2(3) . . . . ?
I1 C1 C6 C5 176.8(3) . . . . ?
I2 C7 C8 F5 -0.5(3) . . . . ?
I2 C7 C8 C9 177.7(3) . . . . ?
I2 C7 C12 F8 3.2(3) . . . . ?
I2 C7 C12 C11 -178.2(3) . . . . ?
F1 C2 C1 C6 -176.7(3) . . . . ?
F1 C2 C3 F2 -0.8(4) . . . . ?
F1 C2 C3 C4 177.0(3) . . . . ?
F2 C3 C2 C1 -179.6(3) . . . . ?
F2 C3 C4 C5 178.0(3) . . . . ?
F2 C3 C4 C10 -0.8(4) . . . . ?
F3 C5 C4 C3 179.1(3) . . . . ?
F3 C5 C4 C10 -2.1(5) . . . . ?
F3 C5 C6 F4 -0.8(4) . . . . ?
F3 C5 C6 C1 -178.8(3) . . . . ?
F4 C6 C1 C2 -178.8(3) . . . . ?
F4 C6 C5 C4 177.2(3) . . . . ?
F5 C8 C7 C12 -179.4(4) . . . . ?
F5 C8 C9 F6 0.3(4) . . . . ?
F5 C8 C9 C10 178.9(3) . . . . ?
F6 C9 C8 C7 -177.9(3) . . . . ?
F6 C9 C10 C4 -0.9(4) . . . . ?
F6 C9 C10 C11 178.9(3) . . . . ?
F7 C11 C10 C4 -3.6(4) . . . . ?
F7 C11 C10 C9 176.6(3) . . . . ?
F7 C11 C12 F8 1.5(4) . . . . ?
F7 C11 C12 C7 -177.1(3) . . . . ?
F8 C12 C7 C8 -177.9(3) . . . . ?
F8 C12 C11 C10 179.0(3) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C1 C6 C5 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C10 -178.6(3) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C3 C4 C10 C9 124.4(4) . . . . ?
C3 C4 C10 C11 -55.4(4) . . . . ?
C4 C10 C9 C8 -179.5(4) . . . . ?
C4 C10 C11 C12 179.0(3) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C7 C12 C11 C10 0.3(4) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
N1 C13 C14 N2 -2.7(5) . . . . ?
N1 C13 C14 C17 177.5(4) . . . . ?
N1 C16 C15 N2 -3.8(5) . . . . ?
N2 C15 C16 C18 177.6(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.639437
2 0.360563
