The C–I⋯O halogen bonding in crown ether chemistry
Wang, Weizhou; Ji, Baoming; CrystEngComm 26 (2024) 5309–5313; doi:10.1039/D4CE00853G

data_7249329
_publ_section_title
;
 The C--I&#x22EF;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         'C6 F4 I2, 2(H2 O), C10 H20 O5'
_chemical_formula_sum            'C16 H24 F4 I2 O7'
_chemical_formula_weight         658.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2023-07-17 deposited with the CCDC.	2024-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.285(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4810(5)
_cell_length_b                   22.1452(19)
_cell_length_c                   14.6860(11)
_cell_measurement_reflns_used    3637
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0270
_cell_measurement_theta_min      3.8870
_cell_volume                     2367.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(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 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00  25.00   1.00    2.00    --  -13.48 -99.00-180.00   45
  2  \w    -20.00  25.00   1.00    2.00    --  -13.48 -99.00  30.00   45
  3  \w    -35.00  53.00   1.00    2.00    --  -13.48  77.00  90.00   88
  4  \w     -8.00  48.00   1.00    2.00    --  -13.48  19.00  60.00   56
  5  \w    -71.00 -29.00   1.00    2.00    --  -13.48 -77.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0702349000
_diffrn_orient_matrix_UB_12      -0.0202316000
_diffrn_orient_matrix_UB_13      0.0055833000
_diffrn_orient_matrix_UB_21      -0.0662247000
_diffrn_orient_matrix_UB_22      0.0232033000
_diffrn_orient_matrix_UB_23      -0.0132371000
_diffrn_orient_matrix_UB_31      -0.0131555000
_diffrn_orient_matrix_UB_32      -0.0088361000
_diffrn_orient_matrix_UB_33      -0.0474966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0594
_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/[\s^2^(Fo^2^)+(0.0410P)^2^+7.9130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3201
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00853g2.cif
_cod_data_source_block           C5-I13-W
_cod_depositor_comments
'Adding full bibliography for 7249319--7249331.cif.'
_cod_database_code               7249329
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.506
_shelx_estimated_absorpt_t_min   0.374
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C7-C8 = C9-C10 = C11-C12 = C13-C14 = C15-C16
 1.52 with sigma of 0.01
 O3-C8 = O3-C9 = O4-C10 = O4-C11 = O5-C12 = O5-C13
 1.45 with sigma of 0.02
 O6-C14 = O6-C15 = O7-C16 = O7-C7
 1.45 with sigma of 0.02
 C8-C9 \\sim C10-C11 \\sim C12-C13 \\sim C14-C15 \\sim C16-C7
 with sigma of 0.02
 C15-O7 \\sim C7-O3 \\sim C9-O4 \\sim C11-O5 \\sim C13-O6
 with sigma of 0.02
 O3-C10 \\sim O4-C12 \\sim O5-C14 \\sim O6-C16 \\sim O7-C8
 with sigma of 0.02
3. Rigid bond restraints
 O3, C9, C10, O4, C11, C12, O5, C13, C14, O6, C15, C16, O7, C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O3 \\sim C9 \\sim C10 \\sim O4 \\sim C11 \\sim C12 \\sim O5 \\sim C13 \\sim C14
\\sim O6 \\sim C15 \\sim C16 \\sim O7 \\sim C7 \\sim C8: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
5.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
;
_shelx_shelxl_version_number     2014/7
_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 3.180
_oxdiff_exptl_absorpt_empirical_full_min 0.572