#------------------------------------------------------------------------------
#$Date: 2025-11-27 00:50:05 +0100 (Thu 27 de Nov de 2025) $
#$Revision: 303448 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/13/7251334.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_7251334
loop_
_publ_author_name
'Bear, Joseph C.'
'Cockcroft, Jeremy Karl'
'Rosu-Finsen, Alexander'
'Williams, Jeffrey Huw'
_publ_section_title
;
 Exploring non-covalent interactions in binary aromatic complexes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00989H
_journal_year                    2025
_chemical_formula_moiety         'C6 F4 I2, C8 H10'
_chemical_formula_sum            'C14 H10 F4 I2'
_chemical_formula_weight         508.02
_chemical_name_systematic        p-xylene:p-diiodotetrafluorobenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.450(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5140(7)
_cell_length_b                   8.5541(8)
_cell_length_c                   10.2442(8)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.4740
_cell_measurement_theta_min      3.3890
_cell_volume                     744.73(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  16.00   0.50    2.50    --    0.12  85.00 -74.00   82
  2  ω    -41.00  27.00   0.50    2.50    --    0.12 -85.00 166.00  136
  3  ω      3.00  42.00   0.50    2.50    --    0.12-108.00 -52.61   78
  4  ω     33.00  64.00   0.50    2.50    --    0.12  77.00 150.00   62
  5  ω    -65.00   8.00   0.50    2.50    --    0.12 -38.00-150.00  146
  6  ω    -17.00  63.00   0.50    2.50    --    0.12  77.00 -30.00  160
  7  ω    -67.00  16.00   0.50    2.50    --    0.12 -57.00  30.00  166
  8  ω    -16.00  24.00   0.50    2.50    --    0.12  77.00 150.00   80
  9  ω     46.00  72.00   0.50    2.50    --   18.00-130.00-118.96   52
 10  ω     26.00  68.00   0.50    2.50    --   22.00-115.00  71.57   84
 11  ω     50.00  78.00   0.50    2.50    --   22.00-133.00 -24.04   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0533307000
_diffrn_orient_matrix_UB_12      0.0424897000
_diffrn_orient_matrix_UB_13      -0.0424055000
_diffrn_orient_matrix_UB_21      0.0596183000
_diffrn_orient_matrix_UB_22      0.0094897000
_diffrn_orient_matrix_UB_23      -0.0448074000
_diffrn_orient_matrix_UB_31      -0.0240484000
_diffrn_orient_matrix_UB_32      -0.0705424000
_diffrn_orient_matrix_UB_33      -0.0316337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6318
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.379
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.355
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_preparation       'Prepared as a 2:1 molar ratio'
_exptl_crystal_recrystallization_method 'Grown in the excess p-xylene'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.165
_refine_diff_density_max         2.600
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0418
_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)+(0.0705P)²+0.8958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                874
_reflns_number_total             984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00989h2.cif
_cod_data_source_block           exp_118
_cod_database_code               7251334
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C8 H10 C6 F4 I2'
_chemical_oxdiff_usercomment
'Crystal grown from solution in excess p-Xylene (1:2)'
_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   0.549
_shelx_estimated_absorpt_t_min   0.404
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_file
;
    exp_118.res created by SHELXL-2014/7

TITL exp_118_auto_a.res in C2/m
REM Old TITL exp_118_auto in C2
REM SHELXT solution in C2/m
REM R1 0.118, Rweak 0.013, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C7 F2 I
CELL 0.71073 8.514 8.5541 10.2442 90 93.45 90
ZERR 2 0.0007 0.0008 0.0008 0 0.007 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H F I
UNIT 28 20 8 4

L.S. 10 0 0
PLAN  5
SIZE 0.16 0.22 0.26
TEMP -123.15
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
SHEL 50 0.74
OMIT -2 4 1
OMIT 1 3 0
OMIT 1 7 0
OMIT 4 0 0
OMIT 6 2 0
OMIT 8 2 0
REM <olex2.extras>
REM <HklSrc "%.\\exp_118.hkl">
REM </olex2.extras>

WGHT    0.070500    0.895800
FVAR       0.40748
I1    4   -0.285555    0.000000    0.227456    10.50000    0.02731    0.05095 =
         0.03571    0.00000    0.01098    0.00000
F1    3   -0.109746    0.275292    0.086991    11.00000    0.03201    0.03209 =
         0.04638   -0.00671    0.00644    0.00288
C1    1   -0.115871    0.000000    0.092359    10.50000    0.01631    0.03726 =
         0.02534    0.00000    0.00269    0.00000
C2    1   -0.057010    0.139059    0.044917    11.00000    0.02057    0.02984 =
         0.03085   -0.00514   -0.00216    0.00409
C3    1    0.067037    0.361645    0.542151    11.00000    0.02790    0.03814 =
         0.04126    0.00266    0.00228    0.00010
AFIX  43
H3    2    0.112125    0.265008    0.570658    11.00000   -1.20000
AFIX   0
C4    1    0.135662    0.500000    0.585081    10.50000    0.02527    0.04150 =
         0.03515    0.00000    0.00586    0.00000
C5    1    0.281748    0.500000    0.676937    10.50000    0.02907    0.05225 =
         0.04760    0.00000   -0.00287    0.00000
PART -1
AFIX 137
H5A   2    0.260884    0.558237    0.756437    10.50000   -1.50000
H5B   2    0.368513    0.549662    0.633834    10.50000   -1.50000
H5C   2    0.310422    0.392101    0.700007    10.50000   -1.50000
AFIX   0
HKLF 4

REM  exp_118_auto_a.res in C2/m
REM R1 =  0.0418 for     874 Fo > 4sig(Fo)  and  0.0479 for all     984 data
REM     53 parameters refined using      0 restraints

END

WGHT      0.0705      0.8970

REM Highest difference peak  2.600,  deepest hole -0.823,  1-sigma level  0.206
Q1    1  -0.3095  0.0000  0.1422  10.50000  0.05    2.60
Q2    1  -0.2594  0.0000  0.3127  10.50000  0.05    2.53
Q3    1  -0.1345  0.0000  0.3191  10.50000  0.05    1.14
Q4    1  -0.2439  0.0000  0.4001  10.50000  0.05    0.94
Q5    1  -0.2859 -0.0832  0.1831  11.00000  0.05    0.88
;
_shelx_res_checksum              5088
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.930
_oxdiff_exptl_absorpt_empirical_full_min 0.608
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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
I1 I -0.28556(5) 0.0000 0.22746(4) 0.0376(2) Uani 1 2 d S T P . .
F1 F -0.1097(3) 0.2753(3) 0.0870(3) 0.0367(6) Uani 1 1 d . . . . .
C1 C -0.1159(7) 0.0000 0.0924(6) 0.0262(12) Uani 1 2 d S T P . .
C2 C -0.0570(5) 0.1391(5) 0.0449(4) 0.0272(9) Uani 1 1 d . . . . .
C3 C 0.0670(6) 0.3616(6) 0.5422(5) 0.0358(10) Uani 1 1 d . . . . .
H3 H 0.1121 0.2650 0.5707 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1357(8) 0.5000 0.5851(6) 0.0338(14) Uani 1 2 d S T P . .
C5 C 0.2817(9) 0.5000 0.6769(8) 0.0432(16) Uani 1 2 d S T P . .
H5A H 0.2609 0.5582 0.7564 0.065 Uiso 0.5 1 calc R U P A -1
H5B H 0.3685 0.5497 0.6338 0.065 Uiso 0.5 1 calc R U P A -1
H5C H 0.3104 0.3921 0.7000 0.065 Uiso 0.5 1 calc R U P A -1
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
I1 0.0273(3) 0.0510(3) 0.0357(3) 0.000 0.01098(18) 0.000
F1 0.0320(15) 0.0321(14) 0.0464(16) -0.0067(11) 0.0064(11) 0.0029(11)
C1 0.016(3) 0.037(3) 0.025(3) 0.000 0.0027(19) 0.000
C2 0.0206(19) 0.030(2) 0.031(2) -0.0051(15) -0.0022(15) 0.0041(16)
C3 0.028(2) 0.038(3) 0.041(3) 0.0027(19) 0.0023(19) 0.0001(19)
C4 0.025(3) 0.041(3) 0.035(3) 0.000 0.006(2) 0.000
C5 0.029(3) 0.052(4) 0.048(4) 0.000 -0.003(3) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 4 13 0.0920
-3 -10 -7 0.1140
8 4 -10 0.0606
6 1 -13 0.0764
-8 -9 5 0.1471
-10 6 -4 0.1142
5 9 7 0.1173
7 7 7 0.1156
-7 -7 -7 0.1046
5 -3 12 0.0740
9 -7 3 0.0891
2 -3 14 0.0761
-1 4 -13 0.0895
3 3 -13 0.0679
-1 4 14 0.0780
-3 -3 14 0.0949
-2 0 14 0.0778
-7 7 9 0.1108
-8 -1 -11 0.0993
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
C2 C1 I1 121.1(3) . . ?
C2 C1 I1 121.1(3) 6 . ?
C2 C1 C2 117.7(5) . 6 ?
F1 C2 C1 120.1(4) . . ?
F1 C2 C2 118.8(2) . 2 ?
C2 C2 C1 121.1(3) 2 . ?
C3 C3 H3 119.5 2_556 . ?
C4 C3 C3 121.0(3) . 2_556 ?
C4 C3 H3 119.5 . . ?
C3 C4 C3 118.1(6) 6_565 . ?
C3 C4 C5 121.0(3) 6_565 . ?
C3 C4 C5 121.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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
I1 C1 2.060(6) . ?
F1 C2 1.330(5) . ?
C1 C2 1.390(5) . ?
C1 C2 1.390(5) 6 ?
C2 C2 1.377(9) 2 ?
C3 C3 1.389(10) 2_556 ?
C3 H3 0.9500 . ?
C3 C4 1.380(6) . ?
C4 C3 1.380(6) 6_565 ?
C4 C5 1.514(9) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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
I1 C1 C2 F1 0.2(6) . . . . ?
I1 C1 C2 C2 179.7(4) . . . 2 ?
C2 C1 C2 F1 179.8(3) 6 . . . ?
C2 C1 C2 C2 -0.7(9) 6 . . 2 ?
C3 C3 C4 C3 0.2(12) 2_556 . . 6_565 ?
C3 C3 C4 C5 180.0(7) 2_556 . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0653 3.5692 13.1740 -0.1902 -0.7988 -0.5708
-2.9350 -10.1957 -6.6338 0.0046 0.0255 0.9997
7.5388 4.4579 -10.4288 0.2296 0.9590 -0.1659
6.4531 0.9257 -12.5802 0.2287 0.9572 0.1775
-7.5344 -8.5153 5.2909 -0.1844 -0.7671 0.6145
-9.9634 5.6849 -3.5422 0.9231 -0.3813 -0.0494
5.3533 8.8298 7.0320 -0.2085 0.0879 -0.9741
7.2448 6.9818 7.3727 -0.4024 0.1678 -0.9000
-7.4899 -6.6846 -7.3919 0.4289 -0.1788 0.8855
5.0520 -3.2210 12.1353 -0.9209 -0.2731 -0.2782
8.9943 -7.3226 3.1294 -0.9235 0.3265 0.2013
1.8102 -2.9835 13.6754 -0.8032 -0.5332 -0.2657
-1.4748 4.3176 -13.2470 0.8239 0.5466 0.1499
3.4196 3.4151 -13.4620 0.5336 0.8395 0.1027
-0.6666 3.6236 13.7795 -0.3948 -0.6228 -0.6755
-3.3550 -3.2184 13.5513 -0.5325 -0.8378 -0.1210
-2.1070 0.2245 14.3506 -0.4866 -0.7665 -0.4191
-7.1041 6.7069 8.9189 0.2856 -0.7595 -0.5844
-7.5398 -0.6249 -10.6419 0.8268 0.0214 0.5620
