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

data_7249328
_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         'C10 H20 O5, 2(C6 F3 I3)'
_chemical_formula_sum            'C22 H19 F6 I6 O5'
_chemical_formula_weight         1238.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 105.819(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1779(9)
_cell_length_b                   8.4631(4)
_cell_length_c                   25.3518(15)
_cell_measurement_reflns_used    4788
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.2040
_cell_measurement_theta_min      3.9490
_cell_volume                     3339.6(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)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      295.15
_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 0.998
_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    -43.00  52.00   1.00   11.76    --  -15.84  77.00-180.00   95
  2  \w    -45.00  56.00   1.00   11.76    --  -15.84  19.00 120.00  101
  3  \w     35.00  89.00   1.00   11.76    --   16.93 178.00  30.00   54
  4  \w    -83.00 -21.00   1.00   11.76    --  -15.84 -77.00 120.00   62
;
_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      -0.0398856000
_diffrn_orient_matrix_UB_12      -0.0039635000
_diffrn_orient_matrix_UB_13      -0.0204196000
_diffrn_orient_matrix_UB_21      0.0165785000
_diffrn_orient_matrix_UB_22      0.0494047000
_diffrn_orient_matrix_UB_23      -0.0173116000
_diffrn_orient_matrix_UB_31      0.0145566000
_diffrn_orient_matrix_UB_32      -0.0675768000
_diffrn_orient_matrix_UB_33      -0.0113586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9499
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.341
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54554
_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    2.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2252
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.864
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0388
_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/[\s^2^(Fo^2^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                5002
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00853g2.cif
_cod_data_source_block           C5-I135
_cod_depositor_comments
'Adding full bibliography for 7249319--7249331.cif.'
_cod_database_code               7249328
_shelx_estimated_absorpt_t_max   0.333
_shelx_estimated_absorpt_t_min   0.257
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C1-C2 \\sim C3-C4 \\sim C5-C6 \\sim C7-C8 \\sim C9-C10
 with sigma of 0.01
 O1-C1 \\sim O2-C2 \\sim O2-C3 \\sim O3-C4 \\sim O3-C5 \\sim O4-C6 \\sim O4-C7
\\sim O5-C8 \\sim O5-C9 \\sim O1-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-02
_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 1.514
_oxdiff_exptl_absorpt_empirical_full_min 0.668