Sterically crowded 1,4-diiodobenzene as a precursor to difunctional hypervalent iodine compounds
Li, Guobi; Smith, Rhett; Gembicky, Milan; Rheingold, Arnold L.; Protasiewicz, John D.; Chemical Communications  (2022) –; doi:10.1039/D1CC06486J

data_7129496
_publ_section_title
;
 Sterically crowded 1,4-diiodobenzene as a precursor to difunctional
 hypervalent iodine compounds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06486J
_journal_year                    2022
_chemical_formula_moiety         'C54 H64 I2 O8'
_chemical_formula_sum            'C54 H64 I2 O8'
_chemical_formula_weight         1094.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-17 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9600(4)
_cell_length_b                   15.2357(3)
_cell_length_c                   18.1317(4)
_cell_measurement_reflns_used    7589
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.25
_cell_volume                     6066.4(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38417
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.456
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  0.5626
_exptl_absorpt_correction_T_min  0.5095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       blade
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.418
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6222
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0424P)^2^+13.9564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             6222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06486j2.cif
_cod_data_source_block           pro219_200k_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129496
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.731
_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. Restrained distances
 C18-C15 \\sim C17A-C15 \\sim C17-C15 \\sim C16A-C15 \\sim C16-C15 \\sim
C18A-C15
 with sigma of 0.02
 C26-C25 \\sim C27-C25 \\sim C28-C25
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C15, C17, C16A, C16, C18A, C18, C17A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=
 Sof(H18F)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C20(H20), C11(H11), C24(H24), C23(H23), C21(H21), C14(H14), C13(H13)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C27(H27A,H27B,H27C), C8(H8A,H8B,H8C), C26(H26A,H26B,H26C),
 C16(H16A,H16B,H16C), C28(H28A,H28B,H28C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F), C16A(H16D,H16E,H16F)
;
_shelx_res_checksum              17381
_shelx_fab_checksum              3086
_platon_squeeze_special_details
;
A solvent mask was calculated and 78 electrons were 
found in a volume of 1185\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
1[H2O], 1[H2O] per Formula Unit 
which account for 80 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'