#------------------------------------------------------------------------------
#$Date: 2024-01-06 08:39:32 +0100 (sáb 06 de ene de 2024) $
#$Revision: 288770 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/01/1570185.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_1570185
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         'C6 F4 I2, C6 H6'
_chemical_formula_sum            'C12 H6 F4 I2'
_chemical_formula_weight         479.97
_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_block_doi                 10.5517/ccdc.csd.cc2f63h8
_audit_creation_date             2023-04-12
_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                90.233(7)
_cell_angle_beta                 90.118(7)
_cell_angle_gamma                100.763(8)
_cell_formula_units_Z            1
_cell_length_a                   5.6444(7)
_cell_length_b                   5.6487(7)
_cell_length_c                   10.5675(13)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.34
_cell_measurement_theta_min      4.18
_cell_volume                     331.00(7)
_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      180
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_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  0.0731
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3945
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.519
_diffrn_reflns_theta_min         4.183
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    37.606
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.1342
_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    2.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             219
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.170
_refine_diff_density_max         4.273
_refine_diff_density_min         -2.400
_refine_diff_density_rms         0.519
_refine_ls_extinction_coef       0.029(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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1273
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0910
_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)+(0.1847P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1151
_reflns_number_total             1273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04191c3.cif
_cod_data_source_block           s7_a
_cod_depositor_comments
'Adding full bibliography for 1570178--1570188.cif.'
_cod_database_code               1570185
_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), C3B(H3B), C2B(H2B)
;
_shelx_res_file
;
TITL s7_a.res in P-1
    s7_a.res
    created by SHELXL-2018/3 at 10:50:31 on 12-Apr-2023
REM Old TITL s7 in P-1
REM SHELXT solution in P-1
REM R1 0.145, Rweak 0.008, Alpha 0.064, Orientation as input
REM Formula found by SHELXT: C6 F2 I
CELL 1.54178 5.6444 5.6487 10.5675 90.233 90.118 100.763
ZERR 1 0.0007 0.0007 0.0013 0.007 0.007 0.008
LATT 1
SFAC C H F I
UNIT 12 6 4 2
RIGU

L.S. 10
PLAN  20
TEMP -100
CONF
BOND $H
LIST 6
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\s7_a.hkl">
REM </olex2.extras>

WGHT    0.184700    0.530000
EXTI    0.029357
FVAR       1.10483
I1A   4    0.822236    0.178040    0.803799    11.00000    0.04305    0.04364 =
         0.02897   -0.00518    0.01011    0.01467
F1A   3    0.464539    0.536821    0.745278    11.00000    0.05478    0.05565 =
         0.01093   -0.00304    0.00291    0.01953
F2A   3    0.215881    0.784446    0.894916    11.00000    0.06394    0.06030 =
         0.02858    0.00169    0.00083    0.03711
C2A   1    0.483211    0.515937    0.871670    11.00000    0.04365    0.04694 =
         0.01386   -0.00353   -0.00234    0.01270
C1A   1    0.628446    0.368343    0.918950    11.00000    0.03421    0.03312 =
         0.02205    0.00520    0.00967    0.00382
C1B   1   -0.004406    0.192479    0.425961    11.00000    0.09710    0.05416 =
         0.02407    0.00697    0.02313    0.02905
AFIX  43
H1B   2   -0.007855    0.327155    0.372898    11.00000   -1.20000
AFIX   0
C3A   1    0.357905    0.645159    0.948510    11.00000    0.03276    0.03717 =
         0.02374   -0.00248    0.00798    0.01262
C3B   1    0.198859   -0.002759    0.573559    11.00000    0.04731    0.10189 =
         0.02568   -0.01346    0.00113    0.03000
AFIX  43
H3B   2    0.336680   -0.007590    0.624543    11.00000   -1.20000
AFIX   0
C2B   1    0.189502    0.188780    0.499643    11.00000    0.06865    0.06349 =
         0.03805   -0.01924    0.02144   -0.00026
AFIX  43
H2B   2    0.320283    0.321821    0.499502    11.00000   -1.20000
AFIX   0
HKLF 4




REM  s7_a.res in P-1
REM wR2 = 0.2304, GooF = S = 1.086, Restrained GooF = 1.080 for all data
REM R1 = 0.0910 for 1151 Fo > 4sig(Fo) and 0.0959 for all 1273 data
REM 83 parameters refined using 37 restraints

END

WGHT      0.1846      0.5295

REM Highest difference peak  4.274,  deepest hole -2.401,  1-sigma level  0.519
Q1    1   0.8346  0.1733  0.8902  11.00000  0.05    4.27
Q2    1   0.8207  0.1936  0.7077  11.00000  0.05    4.22
Q3    1   0.6391  0.2363  0.6436  11.00000  0.05    1.82
Q4    1   0.4608  0.5241  0.4200  11.00000  0.05    1.75
Q5    1   0.9955  0.1295  0.9552  11.00000  0.05    1.47
Q6    1   0.4742  0.5002  0.8366  11.00000  0.05    1.36
Q7    1   0.8492 -0.0616  0.8166  11.00000  0.05    1.30
Q8    1   0.6618  0.0383  0.8605  11.00000  0.05    1.25
Q9    1   0.1825  0.8454  0.7659  11.00000  0.05    1.24
Q10   1  -0.0281  0.2151  0.3178  11.00000  0.05    1.12
Q11   1   0.0878  0.5861  0.3719  11.00000  0.05    1.09
Q12   1   0.1504 -0.1185  0.5014  11.00000  0.05    1.05
Q13   1   0.4203 -0.0557  0.5530  11.00000  0.05    1.00
Q14   1   0.5024  0.1141  0.5887  11.00000  0.05    0.99
Q15   1   0.4854  0.0837  0.5003  11.00000  0.05    0.98
Q16   1   0.3611  0.4211  0.9658  11.00000  0.05    0.96
Q17   1   0.3331  0.0989  0.8004  11.00000  0.05    0.96
Q18   1   0.3004 -0.2328  0.5217  11.00000  0.05    0.94
Q19   1   0.9914  0.3493  0.7429  11.00000  0.05    0.92
Q20   1  -0.1261  0.1662  0.4329  11.00000  0.05    0.90
;
_shelx_res_checksum              38658
_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 0.82224(12) 0.17804(12) 0.80380(6) 0.0377(6) Uani 1 1 d . . . . .
F1A F 0.4645(15) 0.5368(16) 0.7453(6) 0.0393(17) Uani 1 1 d . . . . .
F2A F 0.2159(18) 0.7844(18) 0.8949(8) 0.048(2) Uani 1 1 d . . . . .
C2A C 0.483(2) 0.516(2) 0.8717(11) 0.034(2) Uani 1 1 d . . . . .
C1A C 0.628(2) 0.368(2) 0.9189(11) 0.030(2) Uani 1 1 d . . . . .
C1B C -0.004(4) 0.192(3) 0.4260(13) 0.056(4) Uani 1 1 d . . . . .
H1B H -0.007855 0.327155 0.372898 0.068 Uiso 1 1 calc R U . . .
C3A C 0.358(2) 0.645(2) 0.9485(11) 0.030(2) Uani 1 1 d . . . . .
C3B C 0.199(3) -0.003(4) 0.5736(13) 0.056(4) Uani 1 1 d . . . . .
H3B H 0.336680 -0.007590 0.624543 0.068 Uiso 1 1 calc R U . . .
C2B C 0.190(3) 0.189(3) 0.4996(15) 0.058(3) Uani 1 1 d . . . . .
H2B H 0.320283 0.321821 0.499502 0.070 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1A 0.0430(8) 0.0436(8) 0.0290(7) -0.0052(4) 0.0101(4) 0.0147(4)
F1A 0.055(4) 0.056(4) 0.011(3) -0.003(3) 0.003(3) 0.020(3)
F2A 0.064(5) 0.060(5) 0.029(4) 0.002(3) 0.001(3) 0.037(4)
C2A 0.044(6) 0.047(6) 0.014(4) -0.004(4) -0.002(4) 0.013(4)
C1A 0.034(5) 0.033(5) 0.022(5) 0.005(4) 0.010(4) 0.004(4)
C1B 0.097(10) 0.054(8) 0.024(6) 0.007(5) 0.023(6) 0.029(8)
C3A 0.033(5) 0.037(5) 0.024(5) -0.002(4) 0.008(4) 0.013(4)
C3B 0.047(8) 0.102(11) 0.026(6) -0.013(6) 0.001(5) 0.030(7)
C2B 0.069(8) 0.063(8) 0.038(7) -0.019(5) 0.021(5) 0.000(6)
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_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-wnhrf 2023
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
F1A C2A C1A 118.8(12) . . ?
F1A C2A C3A 118.9(12) . . ?
C1A C2A C3A 122.3(11) . . ?
C2A C1A I1A 122.5(9) . . ?
C2A C1A C3A 116.3(12) . 2_667 ?
C3A C1A I1A 121.2(9) 2_667 . ?
C3B C1B H1B 119.6 2_556 . ?
C2B C1B H1B 119.6 . . ?
C2B C1B C3B 120.9(15) . 2_556 ?
F2A C3A C2A 118.9(11) . . ?
F2A C3A C1A 119.7(11) . 2_667 ?
C2A C3A C1A 121.4(12) . 2_667 ?
C1B C3B H3B 120.6 2_556 . ?
C2B C3B C1B 118.9(15) . 2_556 ?
C2B C3B H3B 120.6 . . ?
C1B C2B C3B 120.2(15) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
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 2.066(12) . ?
F1A C2A 1.347(14) . ?
F2A C3A 1.349(14) . ?
C2A C1A 1.369(18) . ?
C2A C3A 1.372(18) . ?
C1A C3A 1.406(16) 2_667 ?
C1B H1B 0.9500 . ?
C1B C3B 1.38(3) 2_556 ?
C1B C2B 1.35(3) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.35(3) . ?
C2B H2B 0.9500 . ?
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
F1A C2A C1A I1A 0.4(17) . . . . ?
F1A C2A C1A C3A 179.6(10) . . . 2_667 ?
F1A C2A C3A F2A 1.5(19) . . . . ?
F1A C2A C3A C1A -179.6(10) . . . 2_667 ?
C1A C2A C3A F2A -179.1(11) . . . . ?
C1A C2A C3A C1A 0(2) . . . 2_667 ?
C1B C3B C2B C1B -1(2) 2_556 . . . ?
C3A C2A C1A I1A -178.9(9) . . . . ?
C3A C2A C1A C3A 0(2) . . . 2_667 ?
C3B C1B C2B C3B 1(2) 2_556 . . . ?
