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_7062227
_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 H14 I N2 O4, F6 P'
_chemical_formula_sum            'C14 H14 F6 I N2 O4 P'
_chemical_formula_weight         546.14
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-20
_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                 92.272(2)
_cell_angle_gamma                90
_cell_formula_units_Z            10
_cell_length_a                   15.7548(5)
_cell_length_b                   9.8035(3)
_cell_length_c                   30.8925(8)
_cell_measurement_reflns_used    12192
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.3520
_cell_measurement_theta_min      5.2790
_cell_volume                     4767.7(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 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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   -117.00 -18.00   1.00    1.00    --  -42.17 -37.00-120.00   99
  2  \w   -114.00 -14.00   1.00    1.00    --  -42.17 -57.00   0.00  100
  3  \w    -70.00  31.00   1.00    1.00    --  -42.17  57.00 150.00  101
  4  \w     27.00  98.00   1.00    1.00    --   42.17-125.00-150.00   71
  5  \w      8.00  34.00   1.00    1.00    --   42.17  83.00 -10.32   26
  6  \w     29.00 107.00   1.00    3.00    --  112.00 -94.00   0.00   78
  7  \w    103.00 178.00   1.00    3.00    --  112.00  77.00 120.00   75
  8  \w     29.00 107.00   1.00    3.00    --  112.00 -94.00 150.00   78
  9  \w     40.00 141.00   1.00    3.00    --  112.00 -61.00 150.00  101
 10  \w     39.00 138.00   1.00    3.00    --  112.00 -45.00 -30.00   99
 11  \w     36.00 109.00   1.00    3.00    --  112.00-111.00 -90.00   73
 12  \w     36.00 140.00   1.00    3.00    --  112.00 -30.00  30.00  104
 13  \w     36.00 109.00   1.00    3.00    --  112.00-111.00 -30.00   73
 14  \w     30.00 165.00   1.00    3.00    --  112.00 -15.00 120.00  135
 15  \w     36.00 109.00   1.00    3.00    --  112.00-111.00 120.00   73
 16  \w    103.00 178.00   1.00    3.00    --  112.00  77.00  90.00   75
 17  \w     59.00 178.00   1.00    3.00    --  112.00  15.00  60.00  119
 18  \w   -117.00 -18.00   1.00    1.00    --  -42.17 -37.00 120.00   99
 19  \w    -87.00  -6.00   1.00    1.00    --  -42.17 125.00 -60.00   81
;
_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      -0.0227443000
_diffrn_orient_matrix_UB_12      -0.1456864000
_diffrn_orient_matrix_UB_13      -0.0151318000
_diffrn_orient_matrix_UB_21      0.0094284000
_diffrn_orient_matrix_UB_22      -0.0507211000
_diffrn_orient_matrix_UB_23      0.0471394000
_diffrn_orient_matrix_UB_31      -0.0946923000
_diffrn_orient_matrix_UB_32      0.0301263000
_diffrn_orient_matrix_UB_33      0.0062932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            46343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         2.807
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.766
_exptl_absorpt_correction_T_max  0.455
_exptl_absorpt_correction_T_min  0.234
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.902
_exptl_crystal_description       block
_exptl_crystal_F_000             2660
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.105
_refine_diff_density_max         2.299
_refine_diff_density_min         -2.017
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         9730
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0905P)^2^+35.3482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6316
_reflns_number_total             9730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           4-I-4_PF6
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_database_code               7062227
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
 C37-C34
 1.5 with sigma of 0.01
3. Rigid body (RIGU) restrains
 O38, O39, N31, C32, C33, C34, C35, C36, C37, C40
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 O48, O49, N41, C42, C43, C44, C45, C46, C47, C50
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36),
  C42(H42), C43(H43), C45(H45), C46(H46)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C40(H40A,H40B,
 H40C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              20594
_ins_header
;
TITL OIS-126_numabs_ana in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  15.754791   9.803480  30.892548  90.0000  92.2718  90.0000
ZERR   10.00   0.000466   0.000268   0.000787   0.0000   0.0025   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O F P I
UNIT 140.00 140.00 20.00 40.00 60.00 10.00 10.00
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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.861