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_7062223
_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         'C12 H14 I N2, F6 P'
_chemical_formula_sum            'C12 H14 F6 I N2 P'
_chemical_formula_weight         458.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc279pjs
_audit_creation_date             2020-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-24 deposited with the CCDC.	2023-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6037(5)
_cell_length_b                   12.4587(3)
_cell_length_c                   22.3220(9)
_cell_measurement_reflns_used    4154
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_cell_volume                     3227.0(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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_temperature      170
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15565
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         1.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1037 before and 0.0761 after correction. The Ratio of minimum to maximum transmission is 0.6643. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/pentane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0576P)^2^+1.7161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2665
_reflns_number_total             3542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_database_code               7062223
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.513
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              77964
_olex2_submission_special_instructions 'No special instructions were received'