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_7062226
_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         'C11 H11 I N2 O'
_chemical_formula_sum            'C11 H11 I N2 O'
_chemical_formula_weight         314.12
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   27.1958(6)
_cell_length_b                   27.1958(6)
_cell_length_c                   7.8944(2)
_cell_measurement_reflns_used    10896
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.5760
_cell_measurement_theta_min      3.1750
_cell_volume                     5056.5(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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -115.00 -14.00   1.00    1.00    --  -41.90 -57.00 -60.00  101
  2  \w   -116.00 -18.00   1.00    1.00    --  -41.90 -37.00-180.00   98
  3  \w      7.00  33.00   1.00    1.00    --   41.90  84.00 -41.33   26
  4  \w      7.00  33.00   1.00    1.00    --   41.90  84.00-171.38   26
  5  \w    -21.00  74.00   1.00    1.00    --   41.90 -77.00  60.00   95
  6  \w     36.00 109.00   1.00    4.00    --  112.00-111.00   0.00   73
  7  \w     29.00 107.00   1.00    4.00    --  112.00 -94.00 120.00   78
  8  \w    103.00 178.00   1.00    4.00    --  112.00  77.00   0.00   75
  9  \w     39.00 138.00   1.00    4.00    --  112.00 -45.00-180.00   99
 10  \w     36.00 109.00   1.00    4.00    --  112.00-111.00-150.00   73
 11  \w     39.00 138.00   1.00    4.00    --  112.00 -45.00 -60.00   99
 12  \w     36.00 109.00   1.00    4.00    --  112.00-111.00 -60.00   73
 13  \w     40.00 141.00   1.00    4.00    --  112.00 -61.00  30.00  101
 14  \w     36.00 109.00   1.00    4.00    --  112.00-111.00  60.00   73
 15  \w     24.00 178.00   1.00    4.00    --  112.00   0.00   0.00  154
 16  \w   -115.00 -14.00   1.00    1.00    --  -41.90 -57.00  60.00  101
 17  \w   -116.00 -18.00   1.00    1.00    --  -41.90 -37.00 120.00   98
 18  \w      7.00  33.00   1.00    1.00    --   41.90  84.00  82.30   26
 19  \w      6.00  83.00   1.00    1.00    --   41.90 -99.00 -90.00   77
 20  \w     84.00 178.00   1.00    4.00    --  112.00  30.00-150.00   94
 21  \w     86.00 178.00   1.00    4.00    --  112.00  45.00  60.00   92
 22  \w     59.00 178.00   1.00    4.00    --  112.00  15.00 150.00  119
 23  \w     83.00 178.00   1.00    4.00    --  112.00  61.00 -22.38   95
;
_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      -0.0617804000
_diffrn_orient_matrix_UB_12      -0.0190161000
_diffrn_orient_matrix_UB_13      -0.0494177000
_diffrn_orient_matrix_UB_21      -0.0207354000
_diffrn_orient_matrix_UB_22      -0.0317325000
_diffrn_orient_matrix_UB_23      0.1697942000
_diffrn_orient_matrix_UB_31      0.0057149000
_diffrn_orient_matrix_UB_32      0.0539633000
_diffrn_orient_matrix_UB_33      0.0824469000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.194
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_correction_T_min  0.141
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.857
_exptl_crystal_description       plate
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0164
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+8.8819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0404
_refine_ls_wR_factor_ref         0.0408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2147
_reflns_number_total             2223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           iodo-antipyrine
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_original_cell_volume        5056.5(3)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7062226
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 100.00
_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.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              14577
_ins_header
;
TITL OIS-039_numabs in R-3 
REM R-3 (#148 in standard setting)
CELL 1.54184  27.195824  27.195824   7.894367  90.0000  90.0000 120.0000
ZERR   18.00   0.000603   0.000603   0.000209   0.0000   0.0000   0.0000
LATT  3
SYMM -y, x-y, z 
SYMM -x+y,-x, z 
SFAC C H N O I
UNIT 198.00 198.00 36.00 18.00 18.00
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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.833