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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/1/57/01/1570187.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_1570187
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         'C20 H12, 2(C6 F4 I2)'
_chemical_formula_sum            'C32 H12 F8 I4'
_chemical_formula_weight         1056.02
_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                103.6520(10)
_cell_angle_beta                 92.767(2)
_cell_angle_gamma                96.252(2)
_cell_formula_units_Z            1
_cell_length_a                   5.8113(2)
_cell_length_b                   10.2259(4)
_cell_length_c                   13.3298(4)
_cell_measurement_reflns_used    6351
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      3.42
_cell_volume                     762.93(5)
_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 0.985
_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  0.0667
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12061
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.392
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    32.725
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4691
_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            orange
_exptl_crystal_density_diffrn    2.298
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_refine_diff_density_max         2.185
_refine_diff_density_min         -3.180
_refine_diff_density_rms         0.394
_refine_ls_extinction_coef       0.0230(18)
_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   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     159
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0857
_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)+(0.1568P)²+1.8196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2436
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           s2_a
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570187
_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), C5B(H5B), C7B(H7B), C8B(H8B), C9B(H9B)
;
_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
C1A C 0.3131(12) 0.7554(8) 0.3653(6) 0.0302(14) Uani 1 1 d . . . . .
I1A I 0.08535(11) 0.78156(7) 0.24912(5) 0.0538(4) Uani 1 1 d . . . . .
F2A F 0.4801(12) 0.9053(6) 0.6369(4) 0.0582(16) Uani 1 1 d . . . . .
C2A C 0.3226(14) 0.8366(8) 0.4654(6) 0.0339(16) Uani 1 1 d . . . . .
I3A I 0.86211(10) 0.70437(8) 0.63907(5) 0.0545(4) Uani 1 1 d . . . . .
F3A F 0.7537(14) 0.5450(8) 0.4010(5) 0.077(2) Uani 1 1 d . . . . .
C3A C 0.4751(14) 0.8215(8) 0.5418(5) 0.0318(15) Uani 1 1 d . . . . .
F4A F 0.4610(14) 0.5761(7) 0.2515(4) 0.0670(18) Uani 1 1 d . . . . .
C4A C 0.6243(13) 0.7242(8) 0.5235(6) 0.0305(14) Uani 1 1 d . . . . .
C5A C 0.6173(15) 0.6440(9) 0.4250(7) 0.0380(17) Uani 1 1 d . . . . .
C6A C 0.4640(15) 0.6586(8) 0.3478(6) 0.0357(16) Uani 1 1 d . . . . .
F1A F 0.1837(12) 0.9316(7) 0.4889(5) 0.0618(17) Uani 1 1 d . . . . .
C1B C -0.0074(12) 0.8553(7) 0.9659(5) 0.0233(12) Uani 1 1 d . . . . .
C2B C -0.1710(11) 0.9127(7) 1.0368(5) 0.0239(13) Uani 1 1 d . . . . .
C3B C -0.3280(14) 0.8238(8) 1.0708(6) 0.0363(16) Uani 1 1 d . . . . .
H3B H -0.434362 0.859018 1.116561 0.044 Uiso 1 1 calc R U . . .
C4B C -0.3325(16) 0.6789(9) 1.0379(8) 0.0447(19) Uani 1 1 d . . . . .
H4B H -0.437298 0.621734 1.063410 0.054 Uiso 1 1 calc R U . . .
C5B C -0.1852(16) 0.6283(8) 0.9708(7) 0.0415(17) Uani 1 1 d . . . . .
H5B H -0.191843 0.534582 0.948082 0.050 Uiso 1 1 calc R U . . .
C6B C -0.0179(13) 0.7116(7) 0.9325(5) 0.0304(14) Uani 1 1 d . . . . .
C7B C 0.1446(17) 0.6568(9) 0.8645(7) 0.0458(18) Uani 1 1 d . . . . .
H7B H 0.139673 0.563140 0.842078 0.055 Uiso 1 1 calc R U . . .
C8B C 0.3059(17) 0.7373(10) 0.8317(7) 0.048(2) Uani 1 1 d . . . . .
H8B H 0.411557 0.698740 0.786941 0.058 Uiso 1 1 calc R U . . .
C9B C 0.3180(13) 0.8767(8) 0.8631(5) 0.0306(15) Uani 1 1 d . . . . .
H9B H 0.431474 0.930130 0.838784 0.037 Uiso 1 1 calc R U . . .
C10B C 0.1635(12) 0.9398(7) 0.9309(5) 0.0240(13) 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'
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 121.2(6) . . ?
C6A C1A I1A 122.4(6) . . ?
C6A C1A C2A 116.5(7) . . ?
C3A C2A C1A 121.5(7) . . ?
F1A C2A C1A 120.4(7) . . ?
F1A C2A C3A 118.1(7) . . ?
F2A C3A C2A 118.8(7) . . ?
F2A C3A C4A 119.7(7) . . ?
C2A C3A C4A 121.5(7) . . ?
C3A C4A I3A 121.5(6) . . ?
C5A C4A I3A 120.9(6) . . ?
C5A C4A C3A 117.6(7) . . ?
F3A C5A C4A 121.4(8) . . ?
F3A C5A C6A 117.4(8) . . ?
C4A C5A C6A 121.1(7) . . ?
F4A C6A C1A 118.9(7) . . ?
F4A C6A C5A 119.3(7) . . ?
C5A C6A C1A 121.8(7) . . ?
C6B C1B C2B 119.1(6) . . ?
C10B C1B C2B 120.8(6) . . ?
C10B C1B C6B 120.1(7) . . ?
C1B C2B C10B 119.1(6) . 2_577 ?
C3B C2B C1B 117.6(7) . . ?
C3B C2B C10B 123.3(7) . 2_577 ?
C2B C3B H3B 118.8 . . ?
C2B C3B C4B 122.4(8) . . ?
C4B C3B H3B 118.8 . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B C3B 119.0(8) . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B H5B 118.8 . . ?
C4B C5B C6B 122.4(8) . . ?
C6B C5B H5B 118.8 . . ?
C5B C6B C1B 119.4(7) . . ?
C7B C6B C1B 118.6(7) . . ?
C7B C6B C5B 122.0(7) . . ?
C6B C7B H7B 119.5 . . ?
C8B C7B C6B 121.0(8) . . ?
C8B C7B H7B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C7B C8B C9B 121.0(8) . . ?
C9B C8B H8B 119.5 . . ?
C8B C9B H9B 119.2 . . ?
C8B C9B C10B 121.7(8) . . ?
C10B C9B H9B 119.2 . . ?
C1B C10B C2B 120.1(6) . 2_577 ?
C9B C10B C1B 117.6(6) . . ?
C9B C10B C2B 122.3(7) . 2_577 ?
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
C1A I1A 2.072(7) . ?
C1A C2A 1.390(11) . ?
C1A C6A 1.380(11) . ?
F2A C3A 1.350(8) . ?
C2A C3A 1.364(11) . ?
C2A F1A 1.321(9) . ?
I3A C4A 2.080(7) . ?
F3A C5A 1.342(9) . ?
C3A C4A 1.377(11) . ?
F4A C6A 1.358(9) . ?
C4A C5A 1.371(11) . ?
C5A C6A 1.373(12) . ?
C1B C2B 1.445(10) . ?
C1B C6B 1.425(9) . ?
C1B C10B 1.414(10) . ?
C2B C3B 1.385(10) . ?
C2B C10B 1.463(10) 2_577 ?
C3B H3B 0.9300 . ?
C3B C4B 1.440(13) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.323(14) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.416(12) . ?
C6B C7B 1.409(12) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.338(14) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.381(13) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.403(9) . ?
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
C1A C2A C3A F2A 178.5(8) . . . . ?
C1A C2A C3A C4A -0.9(13) . . . . ?
I1A C1A C2A C3A -178.8(6) . . . . ?
I1A C1A C2A F1A 0.8(11) . . . . ?
I1A C1A C6A F4A -1.0(11) . . . . ?
I1A C1A C6A C5A 178.7(7) . . . . ?
F2A C3A C4A I3A -0.8(11) . . . . ?
F2A C3A C4A C5A -178.2(8) . . . . ?
C2A C1A C6A F4A 179.6(8) . . . . ?
C2A C1A C6A C5A -0.7(13) . . . . ?
C2A C3A C4A I3A 178.5(6) . . . . ?
C2A C3A C4A C5A 1.1(13) . . . . ?
I3A C4A C5A F3A 3.9(12) . . . . ?
I3A C4A C5A C6A -178.6(7) . . . . ?
F3A C5A C6A C1A 178.6(8) . . . . ?
F3A C5A C6A F4A -1.7(13) . . . . ?
C3A C4A C5A F3A -178.7(8) . . . . ?
C3A C4A C5A C6A -1.2(13) . . . . ?
C4A C5A C6A C1A 1.0(14) . . . . ?
C4A C5A C6A F4A -179.3(8) . . . . ?
C6A C1A C2A C3A 0.6(13) . . . . ?
C6A C1A C2A F1A -179.8(8) . . . . ?
F1A C2A C3A F2A -1.1(13) . . . . ?
F1A C2A C3A C4A 179.5(8) . . . . ?
C1B C2B C3B C4B -0.1(11) . . . . ?
C1B C6B C7B C8B 0.0(12) . . . . ?
C2B C1B C6B C5B -1.1(9) . . . . ?
C2B C1B C6B C7B -179.1(6) . . . . ?
C2B C1B C10B C2B -2.4(10) . . . 2_577 ?
C2B C1B C10B C9B 179.2(6) . . . . ?
C2B C3B C4B C5B -1.7(13) . . . . ?
C3B C4B C5B C6B 2.0(13) . . . . ?
C4B C5B C6B C1B -0.7(11) . . . . ?
C4B C5B C6B C7B 177.3(8) . . . . ?
C5B C6B C7B C8B -177.9(8) . . . . ?
C6B C1B C2B C3B 1.4(9) . . . . ?
C6B C1B C2B C10B -178.6(6) . . . 2_577 ?
C6B C1B C10B C2B 178.6(6) . . . 2_577 ?
C6B C1B C10B C9B 0.2(9) . . . . ?
C6B C7B C8B C9B -0.2(14) . . . . ?
C7B C8B C9B C10B 0.3(13) . . . . ?
C8B C9B C10B C1B -0.3(10) . . . . ?
C8B C9B C10B C2B -178.7(7) . . . 2_577 ?
C10B C1B C2B C3B -177.7(6) . . . . ?
C10B C1B C2B C10B 2.4(10) . . . 2_577 ?
C10B C1B C6B C5B 178.0(6) . . . . ?
C10B C1B C6B C7B 0.0(10) . . . . ?
C10B C2B C3B C4B 179.9(7) 2_577 . . . ?
