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

data_7131475
_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         'C22 H24 I N3 O5'
_chemical_formula_sum            'C22 H24 I N3 O5'
_chemical_formula_weight         537.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-07 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.429(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4356(3)
_cell_length_b                   7.9667(2)
_cell_length_c                   36.8918(9)
_cell_measurement_reflns_used    6778
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.9130
_cell_measurement_theta_min      2.9230
_cell_volume                     4446.66(18)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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    -62.00 -10.00   1.00    1.00    --  -41.92 125.00  90.00   52
  2  \w   -114.00 -30.00   1.00    1.00    --  -41.92 -37.00 -60.00   84
  3  \w   -129.00  13.00   1.00    1.00    --  -41.92   0.00  90.00  142
  4  \w    -80.00  -6.00   1.00    1.00    --  -41.92 125.00  30.00   74
  5  \w     86.00 178.00   1.00    5.00    --  112.00  30.00-150.00   92
  6  \w     85.00 177.00   1.00    5.00    --  112.00  61.00  30.00   92
  7  \w     41.00  69.00   1.00    5.00    --  112.00 -61.00 -30.00   28
  8  \w    103.00 177.00   1.00    5.00    --  112.00  77.00  90.00   74
  9  \w     93.00 136.00   1.00    5.00    --  112.00  45.00   0.00   43
 10  \w     83.00 118.00   1.00    5.00    --  112.00  61.00 150.00   35
 11  \w    134.00 173.00   1.00    5.00    --  112.00  61.00 150.00   39
 12  \w    103.00 174.00   1.00    5.00    --  112.00  77.00  60.00   71
 13  \w     36.00 105.00   1.00    5.00    --  112.00-111.00  60.00   69
 14  \w    104.00 177.00   1.00    5.00    --  112.00 111.00 -30.00   73
 15  \w     37.00 123.00   1.00    5.00    --  112.00 -77.00 -90.00   86
 16  \w    120.00 166.00   1.00    5.00    --  112.00  77.00 120.00   46
 17  \w     91.00 137.00   1.00    5.00    --  112.00 -61.00 -30.00   46
 18  \w    153.00 178.00   1.00    5.00    --  112.00  45.00   0.00   25
 19  \w     46.00  89.00   1.00    5.00    --  112.00-111.00 -90.00   43
;
_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      0.0534124000
_diffrn_orient_matrix_UB_12      -0.1637078000
_diffrn_orient_matrix_UB_13      0.0009071000
_diffrn_orient_matrix_UB_21      -0.0217369000
_diffrn_orient_matrix_UB_22      -0.0071679000
_diffrn_orient_matrix_UB_23      -0.0425906000
_diffrn_orient_matrix_UB_31      0.0839100000
_diffrn_orient_matrix_UB_32      0.1025603000
_diffrn_orient_matrix_UB_33      -0.0013685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            15985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         2.444
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.646
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.605
_exptl_crystal_description       plate
_exptl_crystal_F_000             2160
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/pentane'
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.018
_refine_diff_density_max         3.620
_refine_diff_density_min         -1.636
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details
;
 Flack x determined using 3400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         8930
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0714
_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^)+(0.1114P)^2^+47.1892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.1958
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                8281
_reflns_number_total             8930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00259d2.cif
_cod_data_source_block           3c
_cod_depositor_comments
'Adding full bibliography for 7131472--7131475.cif.'
_cod_database_code               7131475
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.59
_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. Restrained distances
 O121-C122
 1.3 with sigma of 0.01
 O123-C122
 1.15 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C24) = Uanis(C22)
4. Rigid body (RIGU) restrains
5.a Ternary CH refined with riding coordinates:
 C24(H24), C36(H36), C124(H124), C136(H136)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C108(H10A,H10B),
 C109(H10C,H10D), C111(H11C,H11D), C112(H11E,H11F)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C28(H28), C29(H29), C30(H30), C31(H31),
 C102(H102), C103(H103), C105(H105), C106(H106), C128(H128), C129(H129),
 C130(H130), C131(H131)
5.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C137(H13A,H13B,H13C), C138(H13D,
 H13E,H13F)
;
_shelx_res_checksum              36219
_shelx_hkl_checksum              48968
_ins_header
;
TITL TIO-104_2_numabs_ana2 in I2 
REM I2 (#5 in standard setting)
CELL 1.54184  15.435579   7.966675  36.891780  90.0000 101.4293  90.0000
ZERR    8.00   0.000341   0.000213   0.000850   0.0000   0.0022   0.0000
LATT -2
SYMM -x, y,-z 
SFAC C H N O I
UNIT 176.00 192.00 24.00 40.00 8.00
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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.533