Chiral carbonyl hypoiodites.
Mattila, Milla; Rissanen, Kari; Ward, Jas S.; Chemical communications (Cambridge, England) 59 (2023) 4648–4651; doi:10.1039/d3cc00259d

data_7131474
_publ_section_title
;
 Chiral carbonyl hypoiodites.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4648
_journal_page_last               4651
_journal_paper_doi               10.1039/d3cc00259d
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.8(C22 H24 I N3 O4), 0.2(C22 H22 I N3 O5)'
_chemical_formula_sum            'C22 H23.6 I N3 O4.2'
_chemical_formula_weight         524.14
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2023-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                88.532(2)
_cell_angle_beta                 83.279(2)
_cell_angle_gamma                84.899(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8221(2)
_cell_length_b                   8.3335(2)
_cell_length_c                   16.8477(3)
_cell_measurement_reflns_used    16105
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4210
_cell_measurement_theta_min      2.6130
_cell_volume                     1086.23(4)
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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      8.00  33.00   1.00    1.00    --   42.00  82.00 -13.85   25
  2  \w   -116.00 -66.00   1.00    1.00    --  -42.17 -37.00   0.00   50
  3  \w    -60.00 -24.00   1.00    1.00    --  -42.17 -37.00   0.00   36
  4  \w     10.00  35.00   1.00    1.00    --   42.17  75.00-156.67   25
  5  \w     68.00 110.00   1.00    1.00    --   42.17  57.00  90.00   42
  6  \w     28.00  94.00   1.00    1.00    --   42.17-125.00 -90.00   66
  7  \w     42.00  91.00   1.00    1.00    --   42.17-125.00  60.00   49
  8  \w     14.00  43.00   1.00    1.00    --   42.17  57.00  90.00   29
  9  \w    -29.00  82.00   1.00    1.00    --   42.17 -19.00 -30.00  111
 10  \w     15.00  41.00   1.00    1.00    --   46.00  76.00 -62.66   26
 11  \w     16.00  42.00   1.00    1.00    --   50.00  81.00  52.31   26
 12  \w     16.00  41.00   1.00    1.00    --   50.00  82.00-158.17   25
 13  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 107.83   25
 14  \w     35.00  61.00   1.00    1.00    --   62.00  58.00  81.60   26
 15  \w     30.00  64.00   1.00    1.00    --   62.00  74.00  16.04   34
 16  \w     98.00 134.00   1.00    1.00    --   62.00  74.00  16.04   36
 17  \w     35.00  61.00   1.00    1.00    --   66.00  72.00-156.31   26
 18  \w     94.00 141.00   1.00    1.00    --   66.00  74.00  91.80   47
 19  \w     36.00  62.00   1.00    1.00    --   66.00  74.00  91.80   26
 20  \w    120.00 145.00   1.00    1.00    --   70.00  74.00 -57.23   25
 21  \w     38.00  73.00   1.00    1.00    --   70.00  74.00 -57.23   35
 22  \w     87.00 145.00   1.00    1.00    --   70.00  74.00 -83.33   58
 23  \w     39.00  67.00   1.00    1.00    --   70.00  74.00 -83.33   28
 24  \w     40.00  76.00   1.00    1.00    --   70.00  72.00 -32.41   36
 25  \w     38.00  68.00   1.00    1.00    --   70.00  73.00-129.24   30
 26  \w    110.00 136.00   1.00    1.00    --   74.00  73.00 113.52   26
 27  \w     43.00  68.00   1.00    1.00    --   74.00  73.00 113.52   25
 28  \w     42.00  79.00   1.00    1.00    --   74.00  73.00 136.73   37
 29  \w     68.00 101.00   1.00    1.00    --   98.00  65.00 -57.54   33
 30  \w    149.00 174.00   1.00    1.00    --  102.00  60.00-109.22   25
 31  \w     73.00 101.00   1.00    1.00    --  102.00  60.00-109.22   28
 32  \w     88.00 116.00   1.00    1.00    --  112.00  45.00   0.00   28
 33  \w     84.00 110.00   1.00    1.00    --  112.00  61.00  30.00   26
 34  \w     37.00  99.00   1.00    1.00    --  112.00-111.00 -60.00   62
 35  \w     88.00 115.00   1.00    1.00    --  112.00  45.00-180.00   27
 36  \w    135.00 178.00   1.00    1.00    --  112.00  61.00 -30.00   43
 37  \w     83.00 109.00   1.00    1.00    --  112.00  61.00 -30.00   26
 38  \w    124.00 153.00   1.00    1.00    --  112.00  61.00 120.00   29
 39  \w     30.00 107.00   1.00    1.00    --  112.00 -94.00   0.00   77
 40  \w     83.00 119.00   1.00    1.00    --  112.00  61.00 120.00   36
 41  \w    121.00 171.00   1.00    1.00    --  112.00  61.00 -60.00   50
 42  \w     86.00 118.00   1.00    1.00    --  112.00  61.00 -60.00   32
 43  \w     34.00 105.00   1.00    1.00    --  112.00 -94.00  90.00   71
 44  \w     83.00 176.00   1.00    1.00    --  112.00  61.00-180.00   93
 45  \w     41.00 107.00   1.00    1.00    --  112.00-111.00 -30.00   66
 46  \w    115.00 166.00   1.00    1.00    --  112.00  61.00-120.00   51
 47  \w     84.00 112.00   1.00    1.00    --  112.00  61.00-120.00   28
 48  \w     31.00  89.00   1.00    1.00    --  112.00 -94.00-120.00   58
 49  \w    129.00 177.00   1.00    1.00    --  112.00  64.00 140.99   48
 50  \w     44.00 109.00   1.00    1.00    --  112.00-111.00-150.00   65
 51  \w     83.00 161.00   1.00    1.00    --  112.00  61.00-150.00   78
 52  \w     83.00 157.00   1.00    1.00    --  112.00  61.00  60.00   74
 53  \w     82.00 111.00   1.00    1.00    --  112.00  64.00 140.99   29
 54  \w     84.00 178.00   1.00    1.00    --  112.00  61.00  90.00   94
 55  \w    131.00 157.00   1.00    1.00    --  112.00  61.00   0.00   26
 56  \w     83.00 178.00   1.00    1.00    --  112.00  59.00  19.44   95
 57  \w     83.00 118.00   1.00    1.00    --  112.00  61.00   0.00   35
 58  \w    113.00 139.00   1.00    1.00    --  112.00 -61.00   0.00   26
 59  \w     41.00  91.00   1.00    1.00    --  112.00 -61.00   0.00   50
 60  \w     83.00 163.00   1.00    1.00    --  112.00  61.00 -90.00   80
 61  \w    127.00 152.00   1.00    1.00    --  112.00  45.00  60.00   25
 62  \w     38.00  78.00   1.00    1.00    --  112.00 -94.00 150.00   40
 63  \w     56.00 109.00   1.00    1.00    --  112.00-111.00-120.00   53
 64  \w     88.00 115.00   1.00    1.00    --  112.00  45.00  60.00   27
;
_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      -0.0285336000
_diffrn_orient_matrix_UB_12      0.1852126000
_diffrn_orient_matrix_UB_13      0.0022478000
_diffrn_orient_matrix_UB_21      -0.0221909000
_diffrn_orient_matrix_UB_22      0.0049870000
_diffrn_orient_matrix_UB_23      -0.0897143000
_diffrn_orient_matrix_UB_31      -0.1957503000
_diffrn_orient_matrix_UB_32      -0.0112298000
_diffrn_orient_matrix_UB_33      0.0206353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19075
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.488
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.874
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.206
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.603
_exptl_crystal_description       plate
_exptl_crystal_F_000             526
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 3699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         8298
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0237
_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^)+(0.0329P)^2^+0.6396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                8132
_reflns_number_total             8298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00259d2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7131472--7131475.cif.'
_cod_database_code               7131474
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
3. Others
 Fixed Sof: O12(0.2) O62(0.2) H11A(0.8) H11B(0.8) H61A(0.8) H61B(0.8)
4.a Ternary CH refined with riding coordinates:
 C24(H24), C36(H36), C74(H74), C86(H86)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C28(H28), C29(H29), C30(H30), C31(H31),
 C52(H52), C53(H53), C55(H55), C56(H56), C78(H78), C79(H79), C80(H80), C81(H81)
4.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C87(H87A,H87B,H87C), C88(H88A,H88B,
 H88C)
;
_shelx_res_checksum              96057
_shelx_hkl_checksum              54633
_ins_header
;
TITL TIO-118_numabs in P1 
REM P1 (#1 in standard setting)
CELL 1.54184   7.822090   8.333541  16.847662  88.5322  83.2788  84.8994
ZERR    2.00   0.000188   0.000172   0.000336   0.0016   0.0018   0.0018
LATT -1
SFAC C H N O I
UNIT 44.00 48.00 6.00 8.00 2.00
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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.824