C-H, Si-H and C-F abstraction with an extremely electron poor I(III) reagent
Dutton, Jason Laurence; _, Tania; Barwise, Lachlan; Bennetts, Jason; White, Keith Forrest; Sceney, Marcus; Dalton Transactions  (2023) –; doi:10.1039/D3DT03266C

data_7714167
_publ_section_title
;
 C-H, Si-H and C-F abstraction with an extremely electron poor I(III)
 reagent
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT03266C
_journal_year                    2023
_chemical_formula_moiety         'C25 H19 I N O2, C F3 O3 S, 0.5[C5H12]'
_chemical_formula_sum            'C28.5 H25 F3 I N O5 S'
_chemical_formula_weight         677.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-18 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.27140(10)
_cell_length_b                   21.69800(10)
_cell_length_c                   9.84150(10)
_cell_measurement_reflns_used    48475
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      71.1530
_cell_measurement_theta_min      4.0130
_cell_volume                     5396.48(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -54.00 -14.00   0.50    0.50    --  -38.50 139.00 162.00   80
  2  \w    -61.00 -12.00   0.50    0.50    --  -38.50 130.00 -11.00   98
  3  \w     31.00  93.00   0.50    0.50    --   42.60-130.00 -82.00  124
  4  \w     37.00  95.00   0.50    0.50    --   42.60-139.00 102.00  116
  5  \w    103.00 128.00   0.50    2.00    --  100.00 139.00 162.00   50
  6  \w     62.00 122.00   0.50    2.00    --  100.00-139.00 102.00  120
  7  \w     73.00  99.00   0.50    2.00    --  100.00-130.00 -82.00   52
  8  \w    104.00 130.00   0.50    2.00    --  100.00 130.00 -11.00   52
  9  \w    -48.00  31.00   0.50    0.50    --  -38.50  21.00 -60.00  158
 10  \w   -100.00 -25.00   0.50    0.50    --  -38.50 -43.00 120.00  150
 11  \w    -85.00 -30.00   0.50    0.50    --  -38.50 -21.00   0.00  110
 12  \w    -96.00 -41.00   0.50    0.50    --  -38.50 -43.00 150.00  110
 13  \w    -82.00 -15.00   0.50    0.50    --  -38.50 138.00-120.00  134
 14  \w     21.00  47.00   0.50    0.50    --   42.60  11.00  60.00   52
 15  \w     71.00 103.00   0.50    0.50    --   42.60  43.00  90.00   64
 16  \w     35.00  86.00   0.50    0.50    --   42.60-138.00-180.00  102
 17  \w     26.00  61.00   0.50    0.50    --   42.60  11.00 -30.00   70
 18  \w     71.00 103.00   0.50    0.50    --   42.60  11.00 -30.00   64
 19  \w     -5.00  30.00   0.50    0.50    --   42.60 -89.00-180.00   70
 20  \w     38.00  63.00   0.50    0.50    --   42.60-138.00 -30.00   50
 21  \w     51.00 102.00   0.50    0.50    --   42.60  11.00  60.00  102
 22  \w     23.00  83.00   0.50    0.50    --   42.60  65.00 120.00  120
 23  \w     20.00  46.00   0.50    0.50    --   42.60 -32.00-150.00   52
 24  \w    -16.00   9.00   0.50    0.50    --   42.60 -32.00-150.00   50
 25  \w     30.00  56.00   0.50    0.50    --   42.60  43.00  90.00   52
 26  \w     37.00  63.00   0.50    0.50    --   42.60 -89.00-180.00   52
 27  \w     29.00  77.00   0.50    0.50    --   42.60  54.00   0.00   96
 28  \w    -18.00   8.00   0.50    0.50    --   42.60 -54.00  60.00   52
 29  \w     26.00  51.00   0.50    0.50    --   42.60 -54.00  60.00   50
 30  \w      6.00  55.00   0.50    0.50    --   42.60 -43.00 -60.00   98
 31  \w     75.00 109.00   0.50    2.00    --  100.00 -33.00-150.00   68
 32  \w     69.00  95.00   0.50    2.00    --  100.00 -77.00 -30.00   52
 33  \w    114.00 169.00   0.50    2.00    --  100.00  96.00 -30.00  110
 34  \w     83.00 163.00   0.50    2.00    --  100.00  59.00  30.00  160
 35  \w     92.00 121.00   0.50    2.00    --  100.00 -68.00  30.00   58
 36  \w     91.00 117.00   0.50    2.00    --  100.00 -77.00-120.00   52
 37  \w     42.00  94.00   0.50    2.00    --  100.00 -22.00-159.85  104
 38  \w     86.00 166.00   0.50    2.00    --  100.00  17.00   0.00  160
 39  \w     53.00  79.00   0.50    2.00    --  100.00-117.00   0.00   52
 40  \w     40.00 121.00   0.50    2.00    --  100.00-145.00-150.00  162
 41  \w     87.00 144.00   0.50    2.00    --  100.00 145.00-150.00  114
 42  \w     53.00 124.00   0.50    2.00    --  100.00-145.00  60.00  142
 43  \w     37.00 116.00   0.50    2.00    --  100.00 -50.00-120.00  158
 44  \w     62.00  88.00   0.50    2.00    --  100.00 -33.00 -90.00   52
 45  \w    132.00 171.00   0.50    2.00    --  100.00  17.00-120.00   78
 46  \w     75.00 106.00   0.50    2.00    --  100.00 -96.00 120.00   62
 47  \w    107.00 161.00   0.50    2.00    --  100.00  33.00  90.00  108
 48  \w     40.00 107.00   0.50    2.00    --  100.00 -25.00   0.00  134
 49  \w     72.00  98.00   0.50    2.00    --  100.00-117.00 -60.00   52
 50  \w    118.00 161.00   0.50    2.00    --  100.00  68.00   0.00   86
 51  \w     71.00 102.00   0.50    2.00    --  100.00 -96.00-180.00   62
 52  \w     34.00  64.00   0.50    2.00    --  100.00 -96.00-180.00   60
 53  \w     32.00 101.00   0.50    2.00    --  100.00 -96.00 -90.00  138
 54  \w    106.00 164.00   0.50    2.00    --  100.00 117.00-180.00  116
 55  \w     87.00 131.00   0.50    2.00    --  100.00 145.00-120.00   88
 56  \w     60.00  94.00   0.50    2.00    --  100.00 -96.00 -60.00   68
 57  \w     36.00  61.00   0.50    2.00    --  100.00 -87.00 120.00   50
 58  \w     75.00 127.00   0.50    2.00    --  100.00 -87.00 120.00  104
 59  \w     49.00  74.00   0.50    2.00    --  100.00 -96.00 150.00   50
 60  \w    139.00 165.00   0.50    2.00    --  100.00  77.00 -90.00   52
 61  \w     64.00 114.00   0.50    2.00    --  100.00 -87.00  30.00  100
 62  \w     37.00  77.00   0.50    2.00    --  100.00 -68.00  30.00   80
 63  \w     67.00 109.00   0.50    2.00    --  100.00-117.00 120.00   84
 64  \w     39.00  64.00   0.50    2.00    --  100.00 -77.00-120.00   50
 65  \w     52.00  77.00   0.50    2.00    --  100.00 -77.00-180.00   50
 66  \w    124.00 165.00   0.50    2.00    --  100.00  77.00 150.00   82
 67  \w    101.00 126.00   0.50    2.00    --  100.00-145.00 -30.00   50
 68  \w     60.00 119.00   0.50    2.00    --  100.00 -59.00 120.00  118
 69  \w     75.00 105.00   0.50    2.00    --  100.00 -25.00-120.00   60
 70  \w    112.00 137.00   0.50    2.00    --  100.00  77.00-180.00   50
 71  \w     83.00 109.00   0.50    2.00    --  100.00 -59.00 -60.00   52
 72  \w    109.00 150.00   0.50    2.00    --  100.00 145.00 -60.00   82
 73  \w     65.00 110.00   0.50    2.00    --  100.00 -42.00 -30.00   90
 74  \w    134.00 159.00   0.50    2.00    --  100.00  42.00  60.00   50
 75  \w    102.00 128.00   0.50    2.00    --  100.00  42.00  60.00   52
 76  \w     40.00  82.00   0.50    2.00    --  100.00 -17.00  60.00   84
 77  \w     84.00 109.00   0.50    2.00    --  100.00-117.00-150.00   50
 78  \w     72.00 116.00   0.50    2.00    --  100.00 -68.00-120.00   88
 79  \w    109.00 150.00   0.50    2.00    --  100.00 117.00 -60.00   82
 80  \w     38.00  88.00   0.50    2.00    --  100.00 -59.00-120.00  100
 81  \w     92.00 118.00   0.50    2.00    --  100.00 -77.00-180.00   52
 82  \w     75.00 100.00   0.50    2.00    --  100.00 -79.00 135.21   50
 83  \w     60.00  88.00   0.50    2.00    --  100.00 -50.00  30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0412886000
_diffrn_orient_matrix_UB_12      -0.0197206000
_diffrn_orient_matrix_UB_13      0.1066485000
_diffrn_orient_matrix_UB_21      -0.0448085000
_diffrn_orient_matrix_UB_22      -0.0153342000
_diffrn_orient_matrix_UB_23      0.1005406000
_diffrn_orient_matrix_UB_31      -0.0018877000
_diffrn_orient_matrix_UB_32      -0.0664737000
_diffrn_orient_matrix_UB_33      -0.0548959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            72034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.240
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       Block
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.306
_refine_diff_density_min         -1.713
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5227
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0692P)^2^+9.6158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5028
_reflns_number_total             5227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03266c2.cif
_cod_data_source_block           t455
_cod_original_formula_sum        'C28.50 H25 F3 I N O5 S'
_cod_database_code               7714167
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 I1 S1 O5 F3 N1'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C00I-C00J \\sim C00I-C6
 with sigma of 0.02
 C00J-C00K \\sim C6-C00K
 with sigma of 0.02
 C00J-C00V \\sim C6-C5
 with sigma of 0.02
 C00V-C00W \\sim C5-C4
 with sigma of 0.02
 C00V-C00Z \\sim C5-C0
 with sigma of 0.02
 C00W-C00Y \\sim C4-C3
 with sigma of 0.02
 C00Y-C011 \\sim C3-C2
 with sigma of 0.02
 C00Z-C010 \\sim C0-C1
 with sigma of 0.02
 C010-C011 \\sim C1-C2
 with sigma of 0.02
 C00I-C00V \\sim C00I-C5
 with sigma of 0.04
 C00J-C00W \\sim C6-C4
 with sigma of 0.04
 C00J-C00Z \\sim C6-C0
 with sigma of 0.04
 C00K-C00V \\sim C00K-C5
 with sigma of 0.04
 C00V-C00Y \\sim C5-C3
 with sigma of 0.04
 C00V-C010 \\sim C5-C1
 with sigma of 0.04
 C00W-C00Z \\sim C4-C0
 with sigma of 0.04
 C00W-C011 \\sim C4-C2
 with sigma of 0.04
 C00Y-C010 \\sim C3-C1
 with sigma of 0.04
 C00Z-C011 \\sim C0-C2
 with sigma of 0.04
3. Others
 Sof(C0)=Sof(H0)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(C00J)=Sof(H00J)=Sof(C00V)=Sof(C00W)=Sof(H00W)=Sof(C00Y)=Sof(H00Y)=
 Sof(C00Z)=Sof(H00Z)=Sof(C010)=Sof(H010)=Sof(C011)=Sof(H011)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C00J(H00J), C6(H6)
4.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C0(H0),
  C1(H1), C2(H2), C3(H3), C4(H4)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 168 electrons were 
found in a volume of 500\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[C5H12] per Asymmetric Unit 
which account for 168 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              83770
_shelx_fab_checksum              12168
_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 2.312
_oxdiff_exptl_absorpt_empirical_full_min 0.554