#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:34:43 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295233 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249321.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_7249321
loop_
_publ_author_name
'Wang, Weizhou'
'Ji, Baoming'
_publ_section_title
;
 The C--I⋯O halogen bonding in crown ether chemistry
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5309
_journal_page_last               5313
_journal_paper_doi               10.1039/D4CE00853G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C12 H24 O6, C6 F4 I2'
_chemical_formula_sum            'C18 H24 F4 I2 O6'
_chemical_formula_weight         666.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-08-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-08-25 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.012(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2455(5)
_cell_length_b                   10.6548(5)
_cell_length_c                   15.5033(5)
_cell_measurement_reflns_used    6798
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.8580
_cell_measurement_theta_min      3.7470
_cell_volume                     2347.37(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  84.00   1.00    4.89    --   16.93  57.00  60.00   84
  2  ω    -10.00  42.00   1.00    4.89    --   16.93  77.00 150.00   52
  3  ω    -10.00  42.00   1.00    4.89    --   16.93  77.00 -60.00   52
  4  ω     -2.00  86.00   1.00    4.89    --   16.93  38.00  90.00   88
  5  ω    -50.00  34.00   1.00    4.89    --   16.93 -57.00-180.00   84
  6  ω    -52.00  36.00   1.00    4.89    --   16.93 -38.00 -90.00   88
  7  ω    -85.00 -35.00   1.00    4.89    --  -15.84 -38.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0464908000
_diffrn_orient_matrix_UB_12      0.0060761000
_diffrn_orient_matrix_UB_13      0.0131889000
_diffrn_orient_matrix_UB_21      -0.0049222000
_diffrn_orient_matrix_UB_22      0.0577447000
_diffrn_orient_matrix_UB_23      -0.0226017000
_diffrn_orient_matrix_UB_31      -0.0175554000
_diffrn_orient_matrix_UB_32      -0.0324222000
_diffrn_orient_matrix_UB_33      -0.0376954000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12761
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.232
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0109(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0190P)²+2.0558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2552
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00853g2.cif
_cod_data_source_block           C6-I14
_cod_depositor_comments
'Adding full bibliography for 7249319--7249331.cif.'
_cod_database_code               7249321
_shelx_shelxl_version_number     2019/3
_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   0.597
_shelx_estimated_absorpt_t_min   0.447
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
;
_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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.790
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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 0.68794(2) 0.45078(2) 0.37138(2) 0.04894(10) Uani 1 1 d . . . . .
F1 F 0.63747(11) 0.67397(15) 0.49622(11) 0.0649(5) Uani 1 1 d . . . . .
F2 F 0.49632(12) 0.71065(15) 0.59628(11) 0.0675(5) Uani 1 1 d . . . . .
C2 C 0.57032(17) 0.5860(2) 0.49794(15) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.49680(17) 0.6053(2) 0.54912(15) 0.0391(5) Uani 1 1 d . . . . .
C1 C 0.57581(16) 0.4804(2) 0.44726(14) 0.0342(5) Uani 1 1 d . . . . .
O1 O 0.87423(12) 0.39631(17) 0.29128(11) 0.0492(4) Uani 1 1 d . . . . .
O3 O 0.73035(13) 0.00058(18) 0.35357(13) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.92486(13) 0.09497(19) 0.38604(13) 0.0565(5) Uani 1 1 d . . . . .
C9 C 0.6578(2) -0.0652(3) 0.3061(2) 0.0558(7) Uani 1 1 d . . . . .
H9A H 0.629101 -0.125378 0.343160 0.067 Uiso 1 1 calc R U . . .
H9B H 0.683186 -0.110359 0.258671 0.067 Uiso 1 1 calc R U . . .
C5 C 0.92810(17) 0.2885(2) 0.31242(16) 0.0438(6) Uani 1 1 d . . . . .
H5A H 0.987652 0.312140 0.342165 0.053 Uiso 1 1 calc R U . . .
H5B H 0.940921 0.243209 0.260263 0.053 Uiso 1 1 calc R U . . .
C6 C 0.87321(18) 0.2075(2) 0.36964(17) 0.0466(6) Uani 1 1 d . . . . .
H6A H 0.864135 0.250601 0.423537 0.056 Uiso 1 1 calc R U . . .
H6B H 0.811901 0.188582 0.341456 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9136(2) 0.4722(3) 0.22786(19) 0.0501(7) Uani 1 1 d . . . . .
C8 C 0.8083(2) -0.0733(3) 0.3819(2) 0.0641(8) Uani 1 1 d . . . . .
H8A H 0.837785 -0.107051 0.332399 0.077 Uiso 1 1 calc R U . . .
H8B H 0.787661 -0.143009 0.416078 0.077 Uiso 1 1 calc R U . . .
C7 C 0.8775(2) 0.0045(3) 0.4351(2) 0.0634(8) Uani 1 1 d . . . . .
H7A H 0.844889 0.047781 0.479257 0.076 Uiso 1 1 calc R U . . .
H7B H 0.923881 -0.050473 0.464129 0.076 Uiso 1 1 calc R U . . .
H4A H 0.9290(18) 0.419(2) 0.1770(17) 0.046(7) Uiso 1 1 d . . . . .
H4B H 0.970(2) 0.518(3) 0.2563(17) 0.056(8) Uiso 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 0.0033 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'
O O 0.0106 0.0060 '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
F1 C2 C3 118.8(2) . . ?
F1 C2 C1 119.4(2) . . ?
C3 C2 C1 121.8(2) . . ?
F2 C3 C2 118.3(2) . . ?
F2 C3 C1 119.9(2) . 5_666 ?
C2 C3 C1 121.9(2) . 5_666 ?
C2 C1 I1 121.65(18) . . ?
C2 C1 C3 116.3(2) . 5_666 ?
C3 C1 I1 122.03(16) 5_666 . ?
C5 O1 C4 113.01(19) . . ?
C8 O3 C9 114.7(2) . . ?
C6 O2 C7 114.0(2) . . ?
O3 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
O3 C9 C4 108.1(2) . 7_655 ?
H9A C9 H9B 108.4 . . ?
C4 C9 H9A 110.1 7_655 . ?
C4 C9 H9B 110.1 7_655 . ?
O1 C5 H5A 110.1 . . ?
O1 C5 H5B 110.1 . . ?
O1 C5 C6 108.04(19) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
O2 C6 C5 107.9(2) . . ?
O2 C6 H6A 110.1 . . ?
O2 C6 H6B 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O1 C4 C9 109.3(2) . 7_655 ?
O1 C4 H4A 109.6(15) . . ?
O1 C4 H4B 108.1(16) . . ?
C9 C4 H4A 106.3(15) 7_655 . ?
C9 C4 H4B 109.5(16) 7_655 . ?
H4A C4 H4B 114(2) . . ?
O3 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
O3 C8 C7 109.8(2) . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
O2 C7 C8 113.5(2) . . ?
O2 C7 H7A 108.9 . . ?
O2 C7 H7B 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
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 2.073(2) . ?
F1 C2 1.341(3) . ?
F2 C3 1.340(3) . ?
C2 C3 1.373(3) . ?
C2 C1 1.378(3) . ?
C3 C1 1.384(3) 5_666 ?
O1 C5 1.407(3) . ?
O1 C4 1.419(3) . ?
O3 C9 1.412(3) . ?
O3 C8 1.405(3) . ?
O2 C6 1.420(3) . ?
O2 C7 1.426(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C4 1.490(4) 7_655 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.497(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4A 1.01(3) . ?
C4 H4B 1.01(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.492(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
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
F1 C2 C3 F2 -1.1(3) . . . . ?
F1 C2 C3 C1 178.8(2) . . . 5_666 ?
F1 C2 C1 I1 2.2(3) . . . . ?
F1 C2 C1 C3 -178.8(2) . . . 5_666 ?
C3 C2 C1 I1 -179.16(18) . . . . ?
C3 C2 C1 C3 -0.1(4) . . . 5_666 ?
C1 C2 C3 F2 -179.7(2) . . . . ?
C1 C2 C3 C1 0.1(4) . . . 5_666 ?
O1 C5 C6 O2 176.09(19) . . . . ?
O3 C8 C7 O2 -70.5(3) . . . . ?
C9 O3 C8 C7 -176.9(2) . . . . ?
C5 O1 C4 C9 166.2(2) . . . 7_655 ?
C6 O2 C7 C8 82.7(3) . . . . ?
C4 O1 C5 C6 -172.0(2) . . . . ?
C8 O3 C9 C4 -173.4(2) . . . 7_655 ?
C7 O2 C6 C5 -175.8(2) . . . . ?
