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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/1/57/01/1570179.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_1570179
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         'C60, 2(C6 F4 I2)'
_chemical_formula_sum            'C72 F8 I4'
_chemical_formula_weight         1524.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-13
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.9493(4)
_cell_length_b                   17.2771(3)
_cell_length_c                   10.18670(10)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      5.12
_cell_volume                     4390.99(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            35985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.468
_diffrn_reflns_theta_min         3.543
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    23.071
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3927
_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            red
_exptl_crystal_density_diffrn    2.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.093
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.00021(3)
_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   1.094
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     171
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0561P)²+33.8763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1812
_reflns_number_total             2236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           sfull_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               1570179
_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.
;
_shelx_estimated_absorpt_t_max   0.223
_shelx_estimated_absorpt_t_min   0.048
_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
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-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_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
C00A C 0.5287(4) 0.3066(3) 0.5820(10) 0.086(2) Uani 1 1 d . . . . .
F1A F 0.71804(15) 0.5197(2) 0.1459(4) 0.0603(9) Uani 1 1 d . . . . .
I1A I 0.66110(2) 0.65460(2) -0.01315(4) 0.0550(2) Uani 1 1 d . . . . .
F2A F 0.71510(15) 0.79250(19) 0.1508(4) 0.0623(9) Uani 1 1 d . . . . .
C1A C 0.7329(2) 0.5873(3) 0.1958(5) 0.0439(11) Uani 1 1 d . . . . .
C2A C 0.7148(2) 0.6562(3) 0.1436(5) 0.0432(11) Uani 1 1 d . . . . .
C3A C 0.7322(2) 0.7240(3) 0.1978(5) 0.0437(11) Uani 1 1 d . . . . .
C1B C 0.5248(4) 0.3840(6) 0.7783(9) 0.108(3) Uani 1 1 d . . . . .
C2B C 0.5545(4) 0.3463(5) 0.6853(11) 0.091(2) Uani 1 1 d . . . . .
C3B C 0.6021(4) 0.3912(6) 0.6515(13) 0.106(3) Uani 1 1 d . . . . .
C4B C 0.6196(4) 0.3925(6) 0.5234(13) 0.108(3) Uani 1 1 d . . . . .
C5B C 0.6392(4) 0.4683(7) 0.4659(15) 0.114(3) Uani 1 1 d . . . . .
C6B C 0.6209(4) 0.4711(7) 0.3287(12) 0.114(3) Uani 1 1 d . . . . .
C7B C 0.6031(4) 0.5396(7) 0.2758(12) 0.111(3) Uani 1 1 d . . . . .
C8B C 0.5564(6) 0.5373(8) 0.1907(10) 0.123(4) Uani 1 1 d . . . . .
C9B C 0.5293(6) 0.4789(10) 0.1659(8) 0.140(4) Uani 1 1 d . . . . .
C10B C 0.5463(7) 0.4039(8) 0.2188(11) 0.134(3) Uani 1 1 d . . . . .
C11B C 0.5916(5) 0.3990(6) 0.3019(12) 0.115(3) Uani 1 1 d . . . . .
C12B C 0.5899(5) 0.3504(5) 0.4174(15) 0.116(3) Uani 1 1 d . . . . .
C13B C 0.5481(5) 0.3111(4) 0.4505(12) 0.106(3) Uani 1 1 d . . . . .
C14B C 0.500000 0.3153(6) 0.3585(17) 0.117(4) Uani 1 2 d S T P . .
C15B C 0.500000 0.3594(11) 0.2518(19) 0.135(5) Uani 1 2 d S T P . .
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'
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
C2B C00A C00A 117.1(6) . 12_655 ?
C2B C00A C13B 121.4(9) . . ?
C13B C00A C00A 109.7(6) . 12_655 ?
F1A C1A C1A 118.3(3) . 7_645 ?
F1A C1A C2A 121.3(5) . . ?
C2A C1A C1A 120.4(3) . 7_645 ?
C1A C2A I1A 119.7(4) . . ?
C3A C2A I1A 121.7(4) . . ?
C3A C2A C1A 118.7(5) . . ?
F2A C3A C2A 120.6(5) . . ?
F2A C3A C3A 118.5(3) . 7_645 ?
C2A C3A C3A 120.9(3) . 7_645 ?
C1B C1B C2B 122.8(6) 12_655 . ?
C1B C1B C8B 119.4(7) 12_655 4_566 ?
C2B C1B C8B 106.0(10) . 4_566 ?
C00A C2B C3B 116.9(10) . . ?
C1B C2B C00A 120.1(9) . . ?
C1B C2B C3B 110.5(10) . . ?
C4B C3B C2B 119.4(12) . . ?
C4B C3B C7B 118.7(11) . 4_566 ?
C7B C3B C2B 110.0(11) 4_566 . ?
C3B C4B C5B 118.8(12) . . ?
C3B C4B C12B 121.2(11) . . ?
C12B C4B C5B 107.4(11) . . ?
C5B C5B C4B 121.5(17) 4_566 . ?
C5B C5B C6B 118.8(15) 4_566 . ?
C6B C5B C4B 107.2(11) . . ?
C7B C6B C5B 120.1(13) . . ?
C7B C6B C11B 119.7(13) . . ?
C11B C6B C5B 107.6(10) . . ?
C3B C7B C8B 108.8(11) 4_566 . ?
C6B C7B C3B 122.1(13) . 4_566 ?
C6B C7B C8B 118.0(13) . . ?
C7B C8B C1B 104.6(11) . 4_566 ?
C9B C8B C1B 117.6(15) . 4_566 ?
C9B C8B C7B 125.5(15) . . ?
C8B C9B C9B 123.0(11) . 12_655 ?
C8B C9B C10B 119.1(15) . . ?
C9B C9B C10B 106.8(9) 12_655 . ?
C11B C10B C9B 120.2(13) . . ?
C11B C10B C15B 118.2(15) . . ?
C15B C10B C9B 109.2(17) . . ?
C10B C11B C6B 117.3(11) . . ?
C10B C11B C12B 119.9(13) . . ?
C12B C11B C6B 110.8(13) . . ?
C11B C12B C4B 106.9(11) . . ?
C13B C12B C4B 117.9(13) . . ?
C13B C12B C11B 122.8(15) . . ?
C00A C13B C14B 108.3(10) . . ?
C12B C13B C00A 123.2(12) . . ?
C12B C13B C14B 116.8(12) . . ?
C13B C14B C13B 103.8(14) 12_655 . ?
C15B C14B C13B 122.0(8) . 12_655 ?
C15B C14B C13B 122.0(8) . . ?
C10B C15B C10B 108(2) 12_655 . ?
C14B C15B C10B 120.2(11) . 12_655 ?
C14B C15B C10B 120.2(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
C00A C00A 1.434(18) 12_655 ?
C00A C2B 1.411(13) . ?
C00A C13B 1.426(14) . ?
F1A C1A 1.326(6) . ?
I1A C2A 2.085(5) . ?
F2A C3A 1.347(6) . ?
C1A C1A 1.395(11) 7_645 ?
C1A C2A 1.379(7) . ?
C2A C3A 1.366(7) . ?
C3A C3A 1.384(10) 7_645 ?
C1B C1B 1.24(2) 12_655 ?
C1B C2B 1.366(14) . ?
C1B C8B 1.603(16) 4_566 ?
C2B C3B 1.461(14) . ?
C3B C4B 1.376(15) . ?
C3B C7B 1.407(16) 4_566 ?
C4B C5B 1.517(16) . ?
C4B C12B 1.498(19) . ?
C5B C5B 1.30(2) 4_566 ?
C5B C6B 1.471(18) . ?
C6B C7B 1.373(15) . ?
C6B C11B 1.471(17) . ?
C7B C8B 1.454(18) . ?
C8B C9B 1.240(17) . ?
C9B C9B 1.46(3) 12_655 ?
C9B C10B 1.466(18) . ?
C10B C11B 1.415(18) . ?
C10B C15B 1.426(17) . ?
C11B C12B 1.446(17) . ?
C12B C13B 1.290(15) . ?
C13B C14B 1.524(15) . ?
C14B C15B 1.33(3) . ?
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
C00A C00A C2B C1B -1.4(8) 12_655 . . . ?
C00A C00A C2B C3B -139.9(6) 12_655 . . . ?
C00A C00A C13B C12B 142.4(8) 12_655 . . . ?
C00A C00A C13B C14B 0.7(7) 12_655 . . . ?
C00A C2B C3B C4B -0.4(11) . . . . ?
C00A C2B C3B C7B 141.9(8) . . . 4_566 ?
C00A C13B C14B C13B -1.0(11) . . . 12_655 ?
C00A C13B C14B C15B 141.9(10) . . . . ?
F1A C1A C2A I1A 1.9(7) . . . . ?
F1A C1A C2A C3A -178.9(5) . . . . ?
I1A C2A C3A F2A -0.1(7) . . . . ?
I1A C2A C3A C3A 179.8(5) . . . 7_645 ?
C1A C1A C2A I1A -177.3(5) 7_645 . . . ?
C1A C1A C2A C3A 1.9(9) 7_645 . . . ?
C1A C2A C3A F2A -179.3(5) . . . . ?
C1A C2A C3A C3A 0.6(10) . . . 7_645 ?
C1B C1B C2B C00A 1.5(9) 12_655 . . . ?
C1B C1B C2B C3B 142.4(5) 12_655 . . . ?
C1B C2B C3B C4B -142.7(9) . . . . ?
C1B C2B C3B C7B -0.4(10) . . . 4_566 ?
C1B C8B C9B C9B -0.9(12) 4_566 . . 12_655 ?
C1B C8B C9B C10B -140.1(11) 4_566 . . . ?
C2B C00A C13B C12B 0.7(12) . . . . ?
C2B C00A C13B C14B -141.1(8) . . . . ?
C2B C3B C4B C5B 139.0(9) . . . . ?
C2B C3B C4B C12B 1.8(13) . . . . ?
C3B C4B C5B C5B -0.8(13) . . . 4_566 ?
C3B C4B C5B C6B -142.0(9) . . . . ?
C3B C4B C12B C11B 141.3(9) . . . . ?
C3B C4B C12B C13B -1.9(13) . . . . ?
C3B C7B C8B C1B -0.6(9) 4_566 . . 4_566 ?
C3B C7B C8B C9B -141.3(12) 4_566 . . . ?
C4B C5B C6B C7B 141.1(9) . . . . ?
C4B C5B C6B C11B -0.7(9) . . . . ?
C4B C12B C13B C00A 0.7(13) . . . . ?
C4B C12B C13B C14B 139.5(9) . . . . ?
C5B C4B C12B C11B -0.1(10) . . . . ?
C5B C4B C12B C13B -143.4(9) . . . . ?
C5B C5B C6B C7B -1.4(13) 4_566 . . . ?
C5B C5B C6B C11B -143.2(8) 4_566 . . . ?
C5B C6B C7B C3B 0.6(14) . . . 4_566 ?
C5B C6B C7B C8B -139.3(11) . . . . ?
C5B C6B C11B C10B 143.4(9) . . . . ?
C5B C6B C11B C12B 0.7(10) . . . . ?
C6B C7B C8B C1B 144.2(8) . . . 4_566 ?
C6B C7B C8B C9B 3.5(16) . . . . ?
C6B C11B C12B C4B -0.4(10) . . . . ?
C6B C11B C12B C13B 140.7(10) . . . . ?
C7B C3B C4B C5B -0.1(13) 4_566 . . . ?
C7B C3B C4B C12B -137.3(10) 4_566 . . . ?
C7B C6B C11B C10B 1.4(13) . . . . ?
C7B C6B C11B C12B -141.3(9) . . . . ?
C7B C8B C9B C9B 135.4(10) . . . 12_655 ?
C7B C8B C9B C10B -3.8(17) . . . . ?
C8B C1B C2B C00A -140.9(7) 4_566 . . . ?
C8B C1B C2B C3B 0.0(9) 4_566 . . . ?
C8B C9B C10B C11B 2.9(16) . . . . ?
C8B C9B C10B C15B 144.4(13) . . . . ?
C9B C9B C10B C11B -142.2(8) 12_655 . . . ?
C9B C9B C10B C15B -0.7(10) 12_655 . . . ?
C9B C10B C11B C6B -1.7(14) . . . . ?
C9B C10B C11B C12B 137.6(11) . . . . ?
C9B C10B C15B C10B 1.2(16) . . . 12_655 ?
C9B C10B C15B C14B -142.0(12) . . . . ?
C10B C11B C12B C4B -142.0(10) . . . . ?
C10B C11B C12B C13B -1.0(15) . . . . ?
C11B C6B C7B C3B 137.9(11) . . . 4_566 ?
C11B C6B C7B C8B -2.1(12) . . . . ?
C11B C10B C15B C10B 143.5(12) . . . 12_655 ?
C11B C10B C15B C14B 0.3(16) . . . . ?
C11B C12B C13B C00A -136.4(11) . . . . ?
C11B C12B C13B C14B 2.4(13) . . . . ?
C12B C4B C5B C5B 141.8(9) . . . 4_566 ?
C12B C4B C5B C6B 0.5(9) . . . . ?
C12B C13B C14B C13B -145.5(8) . . . 12_655 ?
C12B C13B C14B C15B -2.6(14) . . . . ?
C13B C00A C2B C1B 137.7(8) . . . . ?
C13B C00A C2B C3B -0.8(10) . . . . ?
C13B C14B C15B C10B 137.6(8) 12_655 . . . ?
C13B C14B C15B C10B 1.2(16) . . . . ?
C13B C14B C15B C10B -1.2(16) 12_655 . . 12_655 ?
C13B C14B C15B C10B -137.6(8) . . . 12_655 ?
C15B C10B C11B C6B -139.8(10) . . . . ?
C15B C10B C11B C12B -0.5(14) . . . . ?
