Iodination of antipyrine with [N–I–N]+ and carbonyl hypoiodite iodine(i) complexes
Wilson, Laura M. E.; Rissanen, Kari; Ward, Jas S.; New Journal of Chemistry 47 (2023) 2978–2982; doi:10.1039/D2NJ05349G

data_7062225
_publ_section_title
;
 Iodination of antipyrine with [N--I--N]+ and carbonyl hypoiodite
 iodine(i) complexes
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2978
_journal_page_last               2982
_journal_paper_doi               10.1039/D2NJ05349G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C14 H20 I N4, F6 Sb'
_chemical_formula_sum            'C14 H20 F6 I N4 Sb'
_chemical_formula_weight         606.99
_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             2022-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-20 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.962(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.9324(15)
_cell_length_b                   10.7459(7)
_cell_length_c                   8.4481(5)
_cell_measurement_reflns_used    2429
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5480
_cell_measurement_theta_min      3.3610
_cell_volume                     2351.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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   -104.00 -24.00   1.00    1.50    --  -41.65 -37.00  60.00   80
  2  \w     14.00 115.00   1.00    1.50    --   41.65  57.00   0.00  101
  3  \w     22.00  77.00   1.00    1.50    --   41.65 -99.00  60.00   55
  4  \w    103.00 173.00   1.00    5.00    --  112.00  77.00 -90.00   70
  5  \w     41.00 141.00   1.00    5.00    --  112.00 -61.00 150.00  100
  6  \w     36.00 109.00   1.00    5.00    --  112.00-111.00 -30.00   73
  7  \w     49.00 109.00   1.00    5.00    --  112.00-111.00-180.00   60
  8  \w     30.00 147.00   1.00    5.00    --  112.00 -15.00 -60.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275188000
_diffrn_orient_matrix_UB_12      0.1256635000
_diffrn_orient_matrix_UB_13      -0.0298613000
_diffrn_orient_matrix_UB_21      0.0501205000
_diffrn_orient_matrix_UB_22      0.0692604000
_diffrn_orient_matrix_UB_23      0.0512121000
_diffrn_orient_matrix_UB_31      0.0163800000
_diffrn_orient_matrix_UB_32      -0.0010954000
_diffrn_orient_matrix_UB_33      -0.1725602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.102
_exptl_absorpt_correction_T_max  0.43733
_exptl_absorpt_correction_T_min  0.37721
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.045
_exptl_crystal_size_rad          0.034
_refine_diff_density_max         0.504
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0476P)^2^+1.5211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2176
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           2-I-2_SbF6
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_database_code               7062225
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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: F52(0.5) F53(0.5) F54(0.5) F55(0.5) F56(0.5) F57(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              33951
_shelx_fab_checksum              4015
_ins_header
;
TITL OIS-033_scale in C2/m 
REM C2/m (#12 in standard setting)
CELL 1.54184  25.932396  10.745920   8.448118  90.0000  92.9620  90.0000
ZERR    4.00   0.001514   0.000681   0.000485   0.0000   0.0056   0.0000
LATT  7
SYMM -x, y,-z 
SFAC C H N F Sb I
UNIT 56.00 80.00 16.00 24.00 4.00 4.00
TREF
HKLF 4
END
;
_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.797