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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/1/57/01/1570180.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_1570180
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         'C16 H10, 2(C6 F4 I2)'
_chemical_formula_sum            'C14 H5 F4 I2'
_chemical_formula_weight         502.98
_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
_audit_creation_date             2022-01-20
_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                107.150(2)
_cell_angle_beta                 94.642(2)
_cell_angle_gamma                97.251(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1992(3)
_cell_length_b                   9.2122(5)
_cell_length_c                   12.9134(7)
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.42
_cell_measurement_theta_min      3.61
_cell_volume                     693.58(6)
_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      273.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13339
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.732
_diffrn_reflns_theta_min         3.610
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    35.945
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1839 before and 0.0831 after correction.
The Ratio of minimum to maximum transmission is 0.1781.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             462
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.585
_refine_diff_density_min         -2.428
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       0.0063(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   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0482
_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)+(0.0310P)²+5.5506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             2721
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           sfull_a_CCDC2
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570180
_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. 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
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B)
;
_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
I2A I 0.18611(8) 0.82429(5) 0.35614(4) 0.0441(2) Uani 1 1 d . . . . .
F4A F 0.8487(8) 0.5878(6) 0.5007(6) 0.0698(16) Uani 1 1 d . . . . .
C1A C 0.6556(11) 0.7186(8) 0.6392(7) 0.0388(14) Uani 1 1 d . . . . .
I1A I 0.85831(10) 0.67327(7) 0.75827(6) 0.0703(3) Uani 1 1 d . . . . .
F1A F 0.4490(9) 0.8581(7) 0.7701(4) 0.0616(13) Uani 1 1 d . . . . .
C2A C 0.4862(12) 0.8013(9) 0.6645(6) 0.0391(15) Uani 1 1 d . . . . .
F2A F 0.1931(8) 0.9144(6) 0.6159(4) 0.0551(12) Uani 1 1 d . . . . .
C3A C 0.3551(11) 0.8322(8) 0.5864(6) 0.0361(14) Uani 1 1 d . . . . .
F3A F 0.5977(8) 0.6481(6) 0.3481(4) 0.0578(13) Uani 1 1 d . . . . .
C4A C 0.3862(11) 0.7821(7) 0.4775(6) 0.0320(13) Uani 1 1 d . . . . .
C5A C 0.5566(12) 0.6995(8) 0.4515(6) 0.0384(14) Uani 1 1 d . . . . .
C6A C 0.6919(13) 0.6706(8) 0.5321(7) 0.0420(15) Uani 1 1 d . . . . .
C1B C 1.0180(16) 0.4233(8) -0.0260(5) 0.047(2) Uani 1 1 d . . . . .
C2B C 0.8734(18) 0.2971(10) -0.0158(6) 0.054(2) Uani 1 1 d . . . . .
C3B C 0.7010(19) 0.3287(11) 0.0477(7) 0.063(2) Uani 1 1 d . . . . .
H3B H 0.607441 0.246632 0.055868 0.075 Uiso 1 1 calc R U . . .
C4B C 0.665(2) 0.4748(11) 0.0979(7) 0.067(3) Uani 1 1 d . . . . .
H4B H 0.547491 0.490389 0.138049 0.080 Uiso 1 1 calc R U . . .
C5B C 0.8082(18) 0.6041(10) 0.0887(6) 0.056(2) Uani 1 1 d . . . . .
C6B C 0.774(2) 0.7566(11) 0.1379(7) 0.066(2) Uani 1 1 d . . . . .
H6B H 0.657023 0.774890 0.178355 0.079 Uiso 1 1 calc R U . . .
C7B C 0.913(2) 0.8791(10) 0.1262(7) 0.065(2) Uani 1 1 d . . . . .
H7B H 0.889196 0.979361 0.158089 0.078 Uiso 1 1 calc R U . . .
C8B C 1.0872(19) 0.8523(9) 0.0672(6) 0.058(2) Uani 1 1 d . . . . .
H8B H 1.181372 0.935637 0.061240 0.070 Uiso 1 1 calc R U . . .
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'
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
C2A C1A I1A 122.0(6) . . ?
C6A C1A I1A 120.3(5) . . ?
C6A C1A C2A 117.6(7) . . ?
F1A C2A C1A 120.2(7) . . ?
F1A C2A C3A 117.9(7) . . ?
C3A C2A C1A 121.9(7) . . ?
C2A C3A C4A 121.4(7) . . ?
F2A C3A C2A 119.4(7) . . ?
F2A C3A C4A 119.3(6) . . ?
C3A C4A I2A 122.3(5) . . ?
C3A C4A C5A 117.1(7) . . ?
C5A C4A I2A 120.6(5) . . ?
F3A C5A C4A 120.5(7) . . ?
F3A C5A C6A 118.3(6) . . ?
C4A C5A C6A 121.1(7) . . ?
F4A C6A C1A 121.3(7) . . ?
F4A C6A C5A 117.7(8) . . ?
C1A C6A C5A 120.8(7) . . ?
C2B C1B C1B 119.5(11) . 2_765 ?
C5B C1B C1B 120.8(10) 2_765 2_765 ?
C5B C1B C2B 119.7(8) 2_765 . ?
C3B C2B C1B 118.2(8) . . ?
C8B C2B C1B 118.4(9) 2_765 . ?
C8B C2B C3B 123.3(8) 2_765 . ?
C2B C3B H3B 118.6 . . ?
C4B C3B C2B 122.8(9) . . ?
C4B C3B H3B 118.6 . . ?
C3B C4B H4B 119.9 . . ?
C3B C4B C5B 120.2(10) . . ?
C5B C4B H4B 119.9 . . ?
C1B C5B C4B 118.6(8) 2_765 . ?
C1B C5B C6B 119.7(9) 2_765 . ?
C6B C5B C4B 121.7(10) . . ?
C5B C6B H6B 119.9 . . ?
C7B C6B C5B 120.3(11) . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B C6B 119.9(9) . . ?
C8B C7B H7B 120.0 . . ?
C2B C8B H8B 119.1 2_765 . ?
C7B C8B C2B 121.9(9) . 2_765 ?
C7B C8B H8B 119.1 . . ?
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
I2A C4A 2.076(7) . ?
F4A C6A 1.326(9) . ?
C1A I1A 2.078(7) . ?
C1A C2A 1.378(11) . ?
C1A C6A 1.369(12) . ?
F1A C2A 1.359(9) . ?
C2A C3A 1.362(10) . ?
F2A C3A 1.345(8) . ?
C3A C4A 1.383(10) . ?
F3A C5A 1.336(9) . ?
C4A C5A 1.385(10) . ?
C5A C6A 1.391(11) . ?
C1B C1B 1.429(16) 2_765 ?
C1B C2B 1.421(12) . ?
C1B C5B 1.404(14) 2_765 ?
C2B C3B 1.407(15) . ?
C2B C8B 1.403(13) 2_765 ?
C3B H3B 0.9300 . ?
C3B C4B 1.366(14) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.433(13) . ?
C5B C6B 1.412(13) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.386(16) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.376(16) . ?
C8B H8B 0.9300 . ?
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
I2A C4A C5A F3A 1.3(9) . . . . ?
I2A C4A C5A C6A 179.9(5) . . . . ?
C1A C2A C3A F2A -179.5(7) . . . . ?
C1A C2A C3A C4A -0.1(12) . . . . ?
I1A C1A C2A F1A 1.0(10) . . . . ?
I1A C1A C2A C3A 179.3(6) . . . . ?
I1A C1A C6A F4A 3.5(10) . . . . ?
I1A C1A C6A C5A 179.6(5) . . . . ?
F1A C2A C3A F2A -1.2(11) . . . . ?
F1A C2A C3A C4A 178.2(7) . . . . ?
C2A C1A C6A F4A -178.6(7) . . . . ?
C2A C1A C6A C5A -2.5(11) . . . . ?
C2A C3A C4A I2A 179.0(6) . . . . ?
C2A C3A C4A C5A -0.2(11) . . . . ?
F2A C3A C4A I2A -1.6(10) . . . . ?
F2A C3A C4A C5A 179.3(6) . . . . ?
C3A C4A C5A F3A -179.5(6) . . . . ?
C3A C4A C5A C6A -0.9(11) . . . . ?
F3A C5A C6A F4A -2.8(11) . . . . ?
F3A C5A C6A C1A -179.1(7) . . . . ?
C4A C5A C6A F4A 178.5(7) . . . . ?
C4A C5A C6A C1A 2.3(11) . . . . ?
C6A C1A C2A F1A -176.9(7) . . . . ?
C6A C1A C2A C3A 1.4(11) . . . . ?
C1B C1B C2B C3B -1.2(12) 2_765 . . . ?
C1B C1B C2B C8B -179.7(8) 2_765 . . 2_765 ?
C1B C2B C3B C4B 1.2(13) . . . . ?
C1B C5B C6B C7B -1.2(14) 2_765 . . . ?
C2B C3B C4B C5B -1.1(15) . . . . ?
C3B C4B C5B C1B 1.0(14) . . . 2_765 ?
C3B C4B C5B C6B 178.9(9) . . . . ?
C4B C5B C6B C7B -179.0(9) . . . . ?
C5B C1B C2B C3B 180.0(8) 2_765 . . . ?
C5B C1B C2B C8B 1.5(11) 2_765 . . 2_765 ?
C5B C6B C7B C8B -0.6(14) . . . . ?
C6B C7B C8B C2B 1.4(13) . . . 2_765 ?
C8B C2B C3B C4B 179.6(9) 2_765 . . . ?
