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

data_7131472
_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         'C20 H22 I N3 O4'
_chemical_formula_sum            'C20 H22 I N3 O4'
_chemical_formula_weight         495.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-01 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.167(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0497(6)
_cell_length_b                   10.5607(8)
_cell_length_c                   18.3987(13)
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    170
_cell_measurement_theta_max      28.700
_cell_measurement_theta_min      0.407
_cell_volume                     2062.1(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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_temperature      170
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13537
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.188
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0966 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.7163. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/tert-butylmethylether'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         6319
_refine_ls_number_restraints     337
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0544
_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^)+2.2681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.682
_reflns_number_gt                4185
_reflns_number_total             6319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00259d2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7131472--7131475.cif.'
_cod_database_code               7131472
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.742
_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. Uiso/Uaniso restraints and constraints
C76 \\sim C77 \\sim C78 \\sim C78A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
O74 \\sim O74A \\sim O75 \\sim O75A \\sim N65 \\sim N65A \\sim C66 \\sim C66A
\\sim C67 \\sim C67A \\sim C68 \\sim C68A \\sim C69 \\sim C69A \\sim C70 \\sim
C70A \\sim C71 \\sim C71A \\sim C72 \\sim C72A \\sim C73 \\sim C73A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C73A) = Uanis(C66A)
Uanis(C66) = Uanis(C73)
3. Others
 Sof(O74A)=Sof(O75A)=Sof(N65A)=Sof(C66A)=Sof(C67A)=Sof(C72A)=Sof(C73A)=
 Sof(H64A)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69A)=Sof(C70A)=Sof(H70A)=
 Sof(C71A)=Sof(H71A)=Sof(H76)=Sof(C78A)=Sof(H78D)=Sof(H78E)=Sof(H78F)=1-FVAR(1)
 Sof(O74)=Sof(O75)=Sof(N65)=Sof(H64)=Sof(C66)=Sof(C67)=Sof(C68)=Sof(H68)=
 Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(C73)=
 Sof(H76A)=Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C26(H26), C64(H64), C64(H64A), C76(H76), C76(H76A)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21),
 C52(H52), C53(H53), C55(H55), C56(H56), C68(H68), C68A(H68A), C69(H69),
 C69A(H69A), C70(H70), C70A(H70A), C71(H71), C71A(H71A)
4.c Fitted pentagon refined as free rotating group:
 N65A(C66A,C67A,C72A,C73A)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C77(H77A,H77B,H77C), C78(H78A,H78B,
 H78C), C78A(H78D,H78E,H78F)
;
_shelx_res_checksum              1676
_shelx_hkl_checksum              56346
_olex2_submission_special_instructions 'No special instructions were received'