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

data_7131473
_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_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-28 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.521(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7571(4)
_cell_length_b                   7.3863(2)
_cell_length_c                   12.0704(5)
_cell_measurement_reflns_used    5364
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.9810
_cell_measurement_theta_min      4.8980
_cell_volume                     809.25(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -15.00  33.00   1.00    3.00    --  -47.93  35.00 -90.00   48
  2  \w    -89.00 -54.00   1.00    3.00    --  -47.93 -35.00 112.00   35
  3  \w     60.00  86.00   1.00    3.00    --   48.87  35.00 -90.00   26
  4  \w   -105.00 -68.00   1.00   12.00    --  -88.36 -35.00 112.00   37
  5  \w   -162.00-109.00   1.00   12.00    --  -88.36 -35.00 112.00   53
  6  \w     86.00 170.00   1.00   12.00    --  107.71  35.00 -90.00   84
  7  \w     -2.00  33.00   1.00    3.00    --  -47.93  19.00  30.00   35
  8  \w   -120.00 -75.00   1.00    3.00    --  -47.93-125.00-150.00   45
  9  \w      3.00  48.00   1.00    3.00    --   48.87 -35.00 112.00   45
 10  \w    -37.00 -11.00   1.00   12.00    --  -88.36  45.00  60.00   26
 11  \w    -55.00 -13.00   1.00   12.00    --  -88.36  61.00   0.00   42
 12  \w    -37.00  -9.00   1.00   12.00    --  -88.36  45.00  90.00   28
 13  \w    -35.00 -10.00   1.00   12.00    --  -88.36  45.00-120.00   25
 14  \w    -37.00 -11.00   1.00   12.00    --  -88.36  45.00 -90.00   26
 15  \w    -37.00 -12.00   1.00   12.00    --  -88.36  45.00-150.00   25
 16  \w     35.00  83.00   1.00   12.00    --  107.71 -61.00-180.00   48
 17  \w     40.00  81.00   1.00   12.00    --  107.71 -61.00   0.00   41
 18  \w     98.00 127.00   1.00   12.00    --  107.71 -77.00 -90.00   29
 19  \w     59.00  86.00   1.00   12.00    --  107.71 -77.00 -90.00   27
 20  \w     32.00  58.00   1.00   12.00    --  107.71 -45.00 -90.00   26
 21  \w     32.00  58.00   1.00   12.00    --  107.71 -45.00 120.00   26
 22  \w     78.00 127.00   1.00   12.00    --  107.71 -77.00-180.00   49
 23  \w     57.00 105.00   1.00   12.00    --  107.71 -95.00 150.00   48
 24  \w     33.00  58.00   1.00   12.00    --  107.71 -61.00 -30.00   25
 25  \w     28.00  61.00   1.00   12.00    --  107.71 -45.00  90.00   33
 26  \w     45.00  79.00   1.00   12.00    --  107.71 -61.00 150.00   34
 27  \w     54.00  81.00   1.00   12.00    --  107.71 -61.00-150.00   27
 28  \w     32.00  85.00   1.00   12.00    --  107.71 -61.00 -90.00   53
 29  \w     29.00  56.00   1.00   12.00    --  107.71 -45.00 -60.00   27
 30  \w     62.00  88.00   1.00    3.00    --   48.87  77.00  90.00   26
 31  \w     -3.00  22.00   1.00    3.00    --  -47.93  19.00  60.00   25
 32  \w    -61.00 -36.00   1.00   12.00    --  -88.36  61.00-120.00   25
 33  \w    -37.00 -12.00   1.00   12.00    --  -88.36  45.00  30.00   25
 34  \w    -35.00 -10.00   1.00   12.00    --  -88.36  45.00 -30.00   25
 35  \w     95.00 159.00   1.00   12.00    --  107.71  30.00-180.00   64
 36  \w     57.00  84.00   1.00   12.00    --  107.71 -61.00 -60.00   27
 37  \w     67.00  94.00   1.00   12.00    --  107.71 -95.00   0.00   27
 38  \w     28.00  53.00   1.00   12.00    --  107.71 -45.00   0.00   25
 39  \w     36.00  84.00   1.00   12.00    --  107.71 -61.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001660000
_diffrn_orient_matrix_UB_12      0.0905498000
_diffrn_orient_matrix_UB_13      0.1150348000
_diffrn_orient_matrix_UB_21      0.1690770000
_diffrn_orient_matrix_UB_22      0.0159769000
_diffrn_orient_matrix_UB_23      0.0452131000
_diffrn_orient_matrix_UB_31      -0.0145380000
_diffrn_orient_matrix_UB_32      0.1872043000
_diffrn_orient_matrix_UB_33      -0.0595266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0029
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3052
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.494
_diffrn_reflns_theta_min         4.872
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.76a (Rigaku Oxford Diffraction, 2022)
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    1.348
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2900
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9925\% 
around [1.00 0.00 -0.00] (reciprocal) or [0.96 -0.00 0.28] (direct)
;
_cod_data_source_file            d3cc00259d2.cif
_cod_data_source_block           OHD-4-morpy_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7131472--7131475.cif.'
_cod_database_code               7131473
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.899
_diffrn_oxdiff_digest_frames
;
019f7ff9b767f0dde43da29361dc718508013901bdf
;
_diffrn_oxdiff_digest_hkl
;
0186cc437959e5cadcf4728a25257853718930
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              22234
_shelx_hkl_checksum              55734
_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 2.526
_oxdiff_exptl_absorpt_empirical_full_min 0.514
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2