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#$Date: 2024-01-06 09:39:32 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288770 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570183.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_1570183
loop_
_publ_author_name
'Vainauskas, Jogirdas'
'Borchers, Tristan H.'
'Arhangelskis, Mihails'
'McCormick McPherson, Laura J'
'Spilfogel, Toni S.'
'Hamzehpoor, Ehsan'
'Topić, Filip'
'Coles, Simon J.'
'Perepichka, Dmytro F.'
'Barrett, Christopher J.'
'Friščić, Tomislav'
_publ_section_title
;
 Halogen bonding with carbon: directional assembly of non-derivatised
 aromatic carbon systems into robust supramolecular ladder architectures.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13031
_journal_page_last               13041
_journal_paper_doi               10.1039/d3sc04191c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C12 F8 I2 N2, 0.5(C14 H10)'
_chemical_formula_sum            'C19 H5 F8 I2 N2'
_chemical_formula_weight         667.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                94.026(5)
_cell_angle_beta                 97.548(5)
_cell_angle_gamma                105.520(6)
_cell_formula_units_Z            2
_cell_length_a                   5.9146(8)
_cell_length_b                   9.8631(14)
_cell_length_c                   17.9820(18)
_cell_measurement_reflns_used    6472
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.50
_cell_measurement_theta_min      4.69
_cell_volume                     995.9(2)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14419
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.555
_diffrn_reflns_theta_min         2.494
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    25.594
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    2.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             622
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.075
_refine_diff_density_max         1.090
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       0.0030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0827
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0716P)²+19.0170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2884
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           JV15_transazo_anthracene_01_0m_a
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570183
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C6B(H6B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 1.64357(19) 0.22097(13) 0.77197(5) 0.0745(5) Uani 1 1 d . . . . .
N2A N 0.911(3) 0.2145(16) 0.4319(7) 0.072(3) Uani 1 1 d . . . . .
I2A I 0.22054(17) 0.30312(13) 0.15289(5) 0.0724(5) Uani 1 1 d . . . . .
F1A F 1.2569(16) 0.3897(11) 0.7470(5) 0.072(2) Uani 1 1 d . . . . .
F2A F 0.9582(17) 0.4058(11) 0.6265(5) 0.077(3) Uani 1 1 d . . . . .
F3A F 1.255(2) 0.0962(11) 0.4820(5) 0.083(3) Uani 1 1 d . . . . .
F4A F 1.5533(18) 0.0827(10) 0.6012(5) 0.077(3) Uani 1 1 d . . . . .
F5A F 0.5650(19) 0.3818(11) 0.4466(5) 0.081(3) Uani 1 1 d . . . . .
F6A F 0.2796(18) 0.4094(12) 0.3269(6) 0.081(3) Uani 1 1 d . . . . .
F7A F 0.6132(16) 0.1357(11) 0.1727(5) 0.074(2) Uani 1 1 d . . . . .
F8A F 0.8985(18) 0.1007(11) 0.2922(5) 0.079(3) Uani 1 1 d . . . . .
C1A C 1.416(2) 0.2340(14) 0.6776(6) 0.047(2) Uani 1 1 d . . . . .
N1A N 0.925(2) 0.2763(14) 0.4908(7) 0.067(3) Uani 1 1 d . . . . .
C2A C 1.259(2) 0.3158(14) 0.6824(7) 0.050(3) Uani 1 1 d . . . . .
C3A C 1.101(2) 0.3259(15) 0.6194(7) 0.052(3) Uani 1 1 d . . . . .
C4A C 1.094(2) 0.2541(15) 0.5495(7) 0.052(3) Uani 1 1 d . . . . .
C5A C 1.253(3) 0.1693(14) 0.5462(7) 0.052(3) Uani 1 1 d . . . . .
C6A C 1.410(2) 0.1629(14) 0.6089(7) 0.049(3) Uani 1 1 d . . . . .
C7A C 0.746(2) 0.2396(16) 0.3739(8) 0.057(3) Uani 1 1 d . . . . .
C8A C 0.581(2) 0.3179(15) 0.3806(7) 0.054(3) Uani 1 1 d . . . . .
C9A C 0.432(2) 0.3352(17) 0.3181(7) 0.057(3) Uani 1 1 d . . . . .
C10A C 0.438(2) 0.2748(14) 0.2474(7) 0.048(3) Uani 1 1 d . . . . .
C11A C 0.601(2) 0.1960(15) 0.2403(7) 0.051(3) Uani 1 1 d . . . . .
C12A C 0.744(2) 0.1804(15) 0.3021(8) 0.055(3) Uani 1 1 d . . . . .
C1B C 0.169(3) 0.297(2) -0.0773(8) 0.077(4) Uani 1 1 d . . . . .
H1B H 0.302681 0.323299 -0.100697 0.092 Uiso 1 1 calc R U . . .
C2B C 0.052(4) 0.159(2) -0.0801(9) 0.082(4) Uani 1 1 d . . . . .
H2B H 0.112706 0.093272 -0.104031 0.098 Uiso 1 1 calc R U . . .
C3B C -0.158(4) 0.108(2) -0.0493(9) 0.089(4) Uani 1 1 d . . . . .
H3B H -0.237023 0.011640 -0.053933 0.107 Uiso 1 1 calc R U . . .
C4B C -0.237(3) 0.208(2) -0.0120(9) 0.077(4) Uani 1 1 d . . . . .
H4B H -0.372858 0.177678 0.010275 0.092 Uiso 1 1 calc R U . . .
C5B C -0.124(2) 0.3522(18) -0.0060(7) 0.059(3) Uani 1 1 d . . . . .
C6B C -0.201(3) 0.4553(19) 0.0325(7) 0.063(3) Uani 1 1 d . . . . .
H6B H -0.335752 0.425516 0.055254 0.076 Uiso 1 1 calc R U . . .
C7B C -0.089(2) 0.5990(18) 0.0388(7) 0.060(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1A N2A C7A 115.3(14) . . ?
C2A C1A I1A 120.1(9) . . ?
C6A C1A I1A 122.4(10) . . ?
C6A C1A C2A 117.5(11) . . ?
N2A N1A C4A 115.9(14) . . ?
F1A C2A C1A 121.1(11) . . ?
F1A C2A C3A 117.5(12) . . ?
C1A C2A C3A 121.4(11) . . ?
F2A C3A C2A 119.2(12) . . ?
F2A C3A C4A 119.6(12) . . ?
C4A C3A C2A 121.3(13) . . ?
C3A C4A N1A 114.4(13) . . ?
C3A C4A C5A 116.3(11) . . ?
C5A C4A N1A 129.2(12) . . ?
F3A C5A C4A 120.0(12) . . ?
F3A C5A C6A 118.8(13) . . ?
C6A C5A C4A 121.2(12) . . ?
F4A C6A C1A 120.1(11) . . ?
F4A C6A C5A 117.7(12) . . ?
C1A C6A C5A 122.2(13) . . ?
C8A C7A N2A 127.8(13) . . ?
C12A C7A N2A 116.6(14) . . ?
C12A C7A C8A 115.6(12) . . ?
F5A C8A C7A 121.8(12) . . ?
F5A C8A C9A 116.9(13) . . ?
C9A C8A C7A 121.2(12) . . ?
F6A C9A C8A 119.3(13) . . ?
F6A C9A C10A 119.7(12) . . ?
C10A C9A C8A 120.9(14) . . ?
C9A C10A I2A 121.3(10) . . ?
C9A C10A C11A 118.2(12) . . ?
C11A C10A I2A 120.5(9) . . ?
F7A C11A C10A 120.1(11) . . ?
F7A C11A C12A 120.0(13) . . ?
C12A C11A C10A 119.8(12) . . ?
F8A C12A C7A 118.3(12) . . ?
C11A C12A F8A 117.5(13) . . ?
C11A C12A C7A 124.2(14) . . ?
C2B C1B H1B 119.9 . . ?
C2B C1B C7B 120.1(18) . 2_565 ?
C7B C1B H1B 119.9 2_565 . ?
C1B C2B H2B 117.7 . . ?
C1B C2B C3B 124.5(19) . . ?
C3B C2B H2B 117.7 . . ?
C2B C3B H3B 122.0 . . ?
C4B C3B C2B 116(2) . . ?
C4B C3B H3B 122.0 . . ?
C3B C4B H4B 118.6 . . ?
C3B C4B C5B 122.8(19) . . ?
C5B C4B H4B 118.6 . . ?
C4B C5B C6B 123.5(15) . . ?
C4B C5B C7B 119.6(16) . 2_565 ?
C6B C5B C7B 116.9(15) . 2_565 ?
C5B C6B H6B 118.1 . . ?
C7B C6B C5B 123.9(14) . . ?
C7B C6B H6B 118.1 . . ?
C1B C7B C5B 116.9(16) 2_565 2_565 ?
C6B C7B C1B 123.8(15) . 2_565 ?
C6B C7B C5B 119.3(14) . 2_565 ?
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
I1A C1A 2.057(11) . ?
N2A N1A 1.167(18) . ?
N2A C7A 1.415(19) . ?
I2A C10A 2.076(12) . ?
F1A C2A 1.331(15) . ?
F2A C3A 1.312(16) . ?
F3A C5A 1.320(15) . ?
F4A C6A 1.321(16) . ?
F5A C8A 1.330(15) . ?
F6A C9A 1.321(17) . ?
F7A C11A 1.333(15) . ?
F8A C12A 1.375(17) . ?
C1A C2A 1.390(19) . ?
C1A C6A 1.368(17) . ?
N1A C4A 1.426(17) . ?
C2A C3A 1.398(18) . ?
C3A C4A 1.389(18) . ?
C4A C5A 1.42(2) . ?
C5A C6A 1.378(18) . ?
C7A C8A 1.41(2) . ?
C7A C12A 1.38(2) . ?
C8A C9A 1.383(19) . ?
C9A C10A 1.376(18) . ?
C10A C11A 1.401(19) . ?
C11A C12A 1.350(18) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.34(3) . ?
C1B C7B 1.42(2) 2_565 ?
C2B H2B 0.9300 . ?
C2B C3B 1.41(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.37(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.39(2) . ?
C5B C6B 1.40(2) . ?
C5B C7B 1.44(2) 2_565 ?
C6B H6B 0.9300 . ?
C6B C7B 1.38(2) . ?
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
I1A C1A C2A F1A 1.8(18) . . . . ?
I1A C1A C2A C3A -179.5(10) . . . . ?
I1A C1A C6A F4A -0.3(18) . . . . ?
I1A C1A C6A C5A 178.5(10) . . . . ?
N2A N1A C4A C3A -178.2(15) . . . . ?
N2A N1A C4A C5A 1(2) . . . . ?
N2A C7A C8A F5A 1(2) . . . . ?
N2A C7A C8A C9A 178.9(15) . . . . ?
N2A C7A C12A F8A 1(2) . . . . ?
N2A C7A C12A C11A -178.8(14) . . . . ?
I2A C10A C11A F7A -1.5(17) . . . . ?
I2A C10A C11A C12A 178.9(10) . . . . ?
F1A C2A C3A F2A 0(2) . . . . ?
F1A C2A C3A C4A 178.9(13) . . . . ?
F2A C3A C4A N1A 0(2) . . . . ?
F2A C3A C4A C5A -179.8(13) . . . . ?
F3A C5A C6A F4A 0(2) . . . . ?
F3A C5A C6A C1A -179.1(13) . . . . ?
F5A C8A C9A F6A -2(2) . . . . ?
F5A C8A C9A C10A 179.0(13) . . . . ?
F6A C9A C10A I2A 2.0(19) . . . . ?
F6A C9A C10A C11A -179.5(13) . . . . ?
F7A C11A C12A F8A 0(2) . . . . ?
F7A C11A C12A C7A 179.4(13) . . . . ?
C1A C2A C3A F2A -179.2(13) . . . . ?
C1A C2A C3A C4A 0(2) . . . . ?
N1A N2A C7A C8A -7(2) . . . . ?
N1A N2A C7A C12A 173.2(15) . . . . ?
N1A C4A C5A F3A -1(2) . . . . ?
N1A C4A C5A C6A 178.5(14) . . . . ?
C2A C1A C6A F4A -179.5(12) . . . . ?
C2A C1A C6A C5A -1(2) . . . . ?
C2A C3A C4A N1A -179.4(13) . . . . ?
C2A C3A C4A C5A 1(2) . . . . ?
C3A C4A C5A F3A 179.0(13) . . . . ?
C3A C4A C5A C6A -2(2) . . . . ?
C4A C5A C6A F4A -179.4(13) . . . . ?
C4A C5A C6A C1A 2(2) . . . . ?
C6A C1A C2A F1A -179.0(12) . . . . ?
C6A C1A C2A C3A 0(2) . . . . ?
C7A N2A N1A C4A -178.9(12) . . . . ?
C7A C8A C9A F6A 180.0(13) . . . . ?
C7A C8A C9A C10A 1(2) . . . . ?
C8A C7A C12A F8A -178.9(12) . . . . ?
C8A C7A C12A C11A 1(2) . . . . ?
C8A C9A C10A I2A -178.8(11) . . . . ?
C8A C9A C10A C11A 0(2) . . . . ?
C9A C10A C11A F7A -180.0(13) . . . . ?
C9A C10A C11A C12A 0(2) . . . . ?
C10A C11A C12A F8A 179.3(12) . . . . ?
C10A C11A C12A C7A -1(2) . . . . ?
C12A C7A C8A F5A -179.3(13) . . . . ?
C12A C7A C8A C9A -1(2) . . . . ?
C1B C2B C3B C4B -2(2) . . . . ?
C2B C3B C4B C5B 2(2) . . . . ?
C3B C4B C5B C6B -179.3(14) . . . . ?
C3B C4B C5B C7B -1(2) . . . 2_565 ?
C4B C5B C6B C7B 179.9(12) . . . . ?
C5B C6B C7B C1B 179.5(12) . . . 2_565 ?
C5B C6B C7B C5B -2(2) . . . 2_565 ?
C7B C1B C2B C3B 3(2) 2_565 . . . ?
C7B C5B C6B C7B 1.8(19) 2_565 . . . ?
