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_7062224
_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         '3(C12 H8 I N4), 3(F6 P), C H2 Cl2'
_chemical_formula_sum            'C37 H26 Cl2 F18 I3 N12 P3'
_chemical_formula_weight         1525.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-18
_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                81.7710(10)
_cell_angle_beta                 75.3160(10)
_cell_angle_gamma                78.7930(10)
_cell_formula_units_Z            2
_cell_length_a                   10.6696(3)
_cell_length_b                   13.9953(3)
_cell_length_c                   18.4479(4)
_cell_measurement_reflns_used    8370
_cell_measurement_temperature    170
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     2601.11(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26897
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         1.491
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0799 before and 0.0634 after correction. The Ratio of minimum to maximum transmission is 0.7613. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         11442
_refine_ls_number_restraints     171
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0208P)^2^+8.8128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9156
_reflns_number_total             11442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05349g2.cif
_cod_data_source_block           5-I-5_PF6
_cod_depositor_comments
'Adding full bibliography for 7062223--7062227.cif.'
_cod_database_code               7062224
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.486
_shelx_estimated_absorpt_t_min   0.419
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 P111, F112, F113, F114, F115, F116, F117
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 P131, F132, F133, F134, F135, F136, F137
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3. Others
 Sof(F136)=Sof(P131)=Sof(F132)=Sof(F133)=Sof(F134)=Sof(F135)=Sof(F137)=1-FVAR(1)
 Sof(P121)=Sof(F122)=Sof(F123)=Sof(F124)=Sof(F125)=Sof(F126)=Sof(F127)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C201(H20A,H20B)
4.b 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), C52(H52), C53(H53), C55(H55), C56(H56)
;
_shelx_res_checksum              26261
_olex2_submission_special_instructions 'No special instructions were received'