Nucleophilic iodonium interactions (NIIs) in 2-coordinate iodine(I) and silver(I) complexes.
Ward, Jas S.; Frontera, Antonio; Rissanen, Kari; Chemical communications (Cambridge, England) 57 (2021) 5094–5097; doi:10.1039/d1cc01505b

data_7128223
_publ_section_title
;
 Nucleophilic iodonium interactions (NIIs) in 2-coordinate iodine(I) and
 silver(I) complexes.
;
_journal_issue                   41
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5094
_journal_page_last               5097
_journal_paper_doi               10.1039/d1cc01505b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C16 H22 I N2, F6 P'
_chemical_formula_sum            'C16 H22 F6 I N2 P'
_chemical_formula_weight         514.22
_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             2020-12-01
_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.	2021-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                100.468(4)
_cell_angle_beta                 94.508(4)
_cell_angle_gamma                106.703(5)
_cell_formula_units_Z            18
_cell_length_a                   17.9543(10)
_cell_length_b                   20.8051(10)
_cell_length_c                   26.6647(10)
_cell_measurement_reflns_used    7435
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.3940
_cell_measurement_theta_min      2.5510
_cell_volume                     9290.4(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_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    6.00    --  -41.90 -57.00   0.00  101
  2  \w   -116.00 -18.00   1.00    6.00    --  -41.90 -37.00  90.00   98
  3  \w     29.00  95.00   1.00    6.00    --   41.90-125.00-180.00   66
  4  \w    -21.00  74.00   1.00    6.00    --   41.90 -77.00-120.00   95
  5  \w     45.00 140.00   1.00   33.00    --  112.00 -61.00 -30.00   95
  6  \w     29.00  61.00   1.00   33.00    --  112.00 -94.00-120.00   32
  7  \w     49.00 165.00   1.00   33.00    --  112.00 -15.00  60.00  116
  8  \w     86.00 116.00   1.00   33.00    --  112.00  45.00 -90.00   30
  9  \w     41.00 140.00   1.00   33.00    --  112.00 -30.00-120.00   99
 10  \w    130.00 164.00   1.00   33.00    --  112.00  45.00 -90.00   34
 11  \w     80.00 107.00   1.00   33.00    --  112.00 -94.00-120.00   27
 12  \w     36.00  63.00   1.00   33.00    --  112.00-111.00  60.00   27
 13  \w     82.00 109.00   1.00   33.00    --  112.00-111.00  60.00   27
 14  \w     36.00 145.00   1.00   33.00    --  112.00 -77.00 150.00  109
 15  \w     89.00 172.00   1.00   33.00    --  112.00  61.00  60.00   83
 16  \w     54.00 108.00   1.00   33.00    --  112.00-105.00 -27.69   54
 17  \w     33.00 108.00   1.00   33.00    --  112.00-104.00 140.06   75
;
_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      -0.0876381000
_diffrn_orient_matrix_UB_12      -0.0138230000
_diffrn_orient_matrix_UB_13      -0.0187993000
_diffrn_orient_matrix_UB_21      0.0208240000
_diffrn_orient_matrix_UB_22      0.0648744000
_diffrn_orient_matrix_UB_23      -0.0227653000
_diffrn_orient_matrix_UB_31      0.0083177000
_diffrn_orient_matrix_UB_32      -0.0431699000
_diffrn_orient_matrix_UB_33      -0.0514604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_unetI/netI     0.1406
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            64635
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.128
_diffrn_reflns_theta_min         2.529
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.440
_exptl_absorpt_correction_T_max  0.49634
_exptl_absorpt_correction_T_min  0.44755
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.654
_exptl_crystal_description       plate
_exptl_crystal_F_000             4572
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/pentane'
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.032
_exptl_crystal_size_rad          0.037
_refine_diff_density_max         2.770
_refine_diff_density_min         -1.948
_refine_diff_density_rms         0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2329
_refine_ls_number_reflns         36261
_refine_ls_number_restraints     1204
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.1163
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1397P)^2^+67.8228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2909
_refine_ls_wR_factor_ref         0.3445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19164
_reflns_number_total             36261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01505b2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7128218--7128225.cif.'
_cod_database_code               7128223
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 98.99
_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. Restrained distances
 C169-C167
 1.45 with sigma of 0.01
 C159-C157
 1.45 with sigma of 0.01
 P261-F269 = P261-F271 = P261-F270 = P261-F268
 1.58 with sigma of 0.01
 C78-C77
 1.5 with sigma of 0.01
 C27-C24
 1.5 with sigma of 0.01
 C157-C158
 1.5 with sigma of 0.01
 H15B-H13A
 -2.2 with sigma of 0.01
 F263-F270
 2.3 with sigma of 0.02
 F263-F268
 2.3 with sigma of 0.02
 F271-F263
 2.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N91A \\sim C92A \\sim C93A \\sim C94A \\sim C95A \\sim C96A \\sim C97A \\sim
C98A \\sim C99A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
N91 \\sim C92 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim
C99: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C97A) = Uanis(C97)
Uanis(C99A) = Uanis(C99)
Uanis(C98A) = Uanis(C98)
Uanis(N91A) = Uanis(N91)
Uanis(C96A) = Uanis(C96)
Uanis(C94A) = Uanis(C94)
Uanis(C93A) = Uanis(C93)
Uanis(C92A) = Uanis(C92)
Uanis(C95A) = Uanis(C95)
4. Rigid body (RIGU) restrains
 N121, C122, C123, C124, C125, C126, C127, C128, C129
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N161, C162, C163, C164, C165, C166, C167, C168, C169
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N71, C72, C73, C74, C75, C76, C77, C78, C79
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N61, C62, C63, C64, C65, C66, C67, C68, C69
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N41, C42, C43, C44, C45, C46, C47, C48, C49
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N21, C22, C23, C24, C25, C26, C27, C28, C29
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N141, C142, C143, C144, C145, C146
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 N81, C82, C83, C84, C85, C86, C87, C87A, C88, C88A, C89, C89A
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 P321, F322, F323, F324, F325, F326, F327
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 P301, F302, F303, F304, F305, F306, F307
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 P311, F312, F313, F314, F315, F316, F317
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 N151, C152, C153, C154, C155, C156, C157, C158, C159
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
5. Others
 Sof(C87A)=Sof(H6GA)=Sof(C88A)=Sof(H0HA)=Sof(H1HA)=Sof(H2HA)=Sof(C89A)=
 Sof(H6HA)=Sof(H7HA)=Sof(H8HA)=1-FVAR(1)
 Sof(C87)=Sof(H5GA)=Sof(C88)=Sof(H7GA)=Sof(H8GA)=Sof(H9GA)=Sof(C89)=Sof(H3HA)=
 Sof(H4HA)=Sof(H5HA)=FVAR(1)
 Sof(C94)=Sof(C93)=Sof(H3IA)=Sof(C92)=Sof(H4IA)=Sof(N91)=Sof(C96)=Sof(H5IA)=
 Sof(C95)=Sof(H6IA)=Sof(C97)=Sof(H7IA)=Sof(C98)=Sof(H9IA)=Sof(H0JA)=Sof(H1JA)=
 Sof(C99)=Sof(H5JA)=Sof(H6JA)=Sof(H7JA)=1-FVAR(2)
 Sof(C93A)=Sof(H9HA)=Sof(C92A)=Sof(H0IA)=Sof(N91A)=Sof(C96A)=Sof(H1IA)=
 Sof(C95A)=Sof(H2IA)=Sof(C94A)=Sof(C97A)=Sof(H8IA)=Sof(C98A)=Sof(H2JA)=
 Sof(H3JA)=Sof(H4JA)=Sof(C99A)=Sof(H8JA)=Sof(H9JA)=Sof(H0KA)=FVAR(2)
 Sof(P311)=Sof(F312)=Sof(F313)=Sof(F314)=Sof(F315)=Sof(F316)=Sof(F317)=0.75*(1-
 FVAR(4))
 Sof(P301)=Sof(F302)=Sof(F303)=Sof(F304)=Sof(F305)=Sof(F306)=Sof(F307)=0.75*
 FVAR(4)
 Sof(F238)=Sof(F239)=Sof(F240)=Sof(F241)=1-FVAR(4)
 Sof(F234)=Sof(F235)=Sof(F236)=Sof(F237)=FVAR(4)
 Sof(F268)=Sof(F269)=Sof(F270)=Sof(F271)=1-FVAR(5)
 Sof(F264)=Sof(F265)=Sof(F266)=Sof(F267)=FVAR(5)
 Fixed Sof: P321(0.25) F322(0.25) F323(0.25) F324(0.25) F325(0.25) F326(0.25)
 F327(0.25)
6.a Free rotating group:
 P301(F302,F303,F304,F305,F306,F307), P311(F312,F313,F314,F315,F316,F317),
 P321(F322,F323,F324,F325,F326,F327)
6.b Ternary CH refined with riding coordinates:
 C7(HD), C17(HO), C27(HZ), C37(H0BA), C47(H1CA), C57(H2DA), C67(H3EA),
 C77(H4FA), C87(H5GA), C87A(H6GA), C97(H7IA), C97A(H8IA), C107(H5KA),
 C117(H6LA), C127(H127), C137(H137), C147(H7MA), C157(H157), C167(H8NA),
 C177(H9OA)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H), C3(HA), C5(HB), C6(HC), C12(HK), C13(HL), C15(HM), C16(HN), C22(HV),
 C23(HW), C25(HX), C26(HY), C32(H6AA), C33(H7AA), C35(H8AA), C36(H9AA),
 C42(H7BA), C43(H8BA), C45(H9BA), C46(H0CA), C52(H8CA), C53(H9CA), C55(H0DA),
 C56(H1DA), C62(H9DA), C63(H0EA), C65(H1EA), C66(H2EA), C75(H0FA), C76(H1FA),
 C72(H2FA), C73(H3FA), C82(H1GA), C83(H2GA), C85(H3GA), C86(H4GA), C93A(H9HA),
 C92A(H0IA), C96A(H1IA), C95A(H2IA), C93(H3IA), C92(H4IA), C96(H5IA), C95(H6IA),
  C102(H1KA), C103(H2KA), C105(H3KA), C106(H4KA), C112(H2LA), C113(H3LA),
 C115(H4LA), C116(H5LA), C122(H122), C123(H123), C125(H125), C126(H126),
 C132(H132), C133(H133), C135(H135), C136(H136), C142(H3MA), C143(H4MA),
 C145(H5MA), C146(H6MA), C152(H152), C153(H153), C155(H155), C156(H156),
 C162(H4NA), C163(H5NA), C165(H6NA), C166(H7NA), C172(H5OA), C173(H6OA),
 C175(H7OA), C176(H8OA)
6.d Fitted hexagon refined as free rotating group:
 C74(C75,C76,N71,C72,C73), C93A(C92A,N91A,C96A,C95A,C94A), C94(C93,C92,N91,C96,
 C95)
6.e Idealised Me refined as rotating group:
 C8(HE,HF,HG), C9(HH,HI,HJ), C18(HP,HQ,HR), C19(HS,HT,HU), C28(H0AA,H1AA,H2AA),
  C29(H3AA,H4AA,H5AA), C38(H1BA,H2BA,H3BA), C39(H4BA,H5BA,H6BA), C48(H2CA,H3CA,
 H4CA), C49(H5CA,H6CA,H7CA), C58(H3DA,H4DA,H5DA), C59(H6DA,H7DA,H8DA), C68(H4EA,
 H5EA,H6EA), C69(H7EA,H8EA,H9EA), C78(H5FA,H6FA,H7FA), C79(H8FA,H9FA,H0GA),
 C88(H7GA,H8GA,H9GA), C88A(H0HA,H1HA,H2HA), C89(H3HA,H4HA,H5HA), C89A(H6HA,H7HA,
 H8HA), C98(H9IA,H0JA,H1JA), C98A(H2JA,H3JA,H4JA), C99(H5JA,H6JA,H7JA),
 C99A(H8JA,H9JA,H0KA), C108(H6KA,H7KA,H8KA), C109(H9KA,H0LA,H1LA), C118(H7LA,
 H8LA,H9LA), C119(H0MA,H1MA,H2MA), C128(H12A,H12B,H12C), C129(H12D,H12E,H12F),
 C138(H13A,H13B,H13C), C139(H13D,H13E,H13F), C148(H8MA,H9MA,H0NA), C149(H1NA,
 H2NA,H3NA), C158(H15A,H15B,H15C), C159(H15D,H15E,H15F), C168(H9NA,H0OA,H1OA),
 C169(H2OA,H3OA,H4OA), C178(H0PA,H1PA,H2PA), C179(H3PA,H4PA,H5PA)
;
_shelx_res_checksum              66436
_ins_header
;
TITL OHD161_scale in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184  17.954293  20.805093  26.664686 100.4681  94.5082 106.7032
ZERR   20.00   0.000964   0.001048   0.000982   0.0036   0.0037   0.0046
LATT  1
SFAC C H N F P I
UNIT 320.00 440.00 40.00 120.00 20.00 20.00
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 2.519
_oxdiff_exptl_absorpt_empirical_full_min 0.528