Gold(I)-catalysed cyclisation of (<i>E</i>)-ketene-<i>N</i>,<i>O</i>-acetals: a synthetic route toward spiro-oxazole-γ-lactones.
Kanikarapu, Suresh; Prasad, Rangu; Sethi, Manoj; Sahoo, Akhila K.; Organic & biomolecular chemistry 22 (2024) 4672–4679; doi:10.1039/d4ob00551a

data_7159953
_publ_section_title
;
 Gold(I)-catalysed cyclisation of
 (<i>E</i>)-ketene-<i>N</i>,<i>O</i>-acetals: a synthetic route toward
 spiro-oxazole-&#x3b3;-lactones.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4672
_journal_page_last               4679
_journal_paper_doi               10.1039/d4ob00551a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H23 I2 N O5 S'
_chemical_formula_sum            'C28 H23 I2 N O5 S'
_chemical_formula_weight         739.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-21
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2021-11-05 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.000(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2400(3)
_cell_length_b                   9.6340(3)
_cell_length_c                   24.0129(5)
_cell_measurement_reflns_used    16821
_cell_measurement_temperature    297.82(10)
_cell_measurement_theta_max      26.8140
_cell_measurement_theta_min      2.1240
_cell_volume                     2829.88(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      297.82(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_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    -24.00  33.00   0.50   10.39    --  -14.97  15.00  55.00  114
  2  \w     -5.00  20.00   0.50   10.39    --   16.22  15.00  55.00   50
  3  \w    -10.00  89.00   0.50   10.39    --   16.22  30.00  60.00  198
  4  \w      6.00  86.00   0.50   10.39    --   16.22  61.00  60.00  160
  5  \w    -36.00  14.00   0.50   10.39    --  -14.97 -94.00 -30.00  100
  6  \w     -7.00  42.00   0.50   10.39    --   16.22 -15.00-115.00   98
  7  \w    -33.00  -8.00   0.50   10.39    --   16.22 -94.00-120.00   50
  8  \w     29.00  71.00   0.50   10.39    --   16.22-125.00-120.00   84
  9  \w    -61.00 -11.00   0.50   10.39    --   16.22 -15.00-115.00  100
 10  \w    -68.00 -29.00   0.50   10.39    --  -14.97 -15.00-115.00   78
 11  \w    -72.00   3.00   0.50   10.39    --  -14.97 -45.00-120.00  150
 12  \w    -61.00 -22.00   0.50   10.39    --  -14.97 125.00-180.00   78
 13  \w    -56.00 -27.00   0.50   10.39    --  -14.97 125.00   0.00   58
 14  \w    -41.00 -12.00   0.50   10.39    --  -14.97 125.00 120.00   58
 15  \w    -36.00  40.00   0.50   10.39    --   16.22 -94.00 150.00  152
 16  \w     14.00  39.00   0.50   10.39    --   16.22-125.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206485000
_diffrn_orient_matrix_UB_12      -0.0122782000
_diffrn_orient_matrix_UB_13      0.0275280000
_diffrn_orient_matrix_UB_21      0.0541458000
_diffrn_orient_matrix_UB_22      0.0072283000
_diffrn_orient_matrix_UB_23      -0.0091875000
_diffrn_orient_matrix_UB_31      -0.0018978000
_diffrn_orient_matrix_UB_32      0.0722360000
_diffrn_orient_matrix_UB_33      0.0056072000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.005
_diffrn_reflns_theta_min         1.895
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    3.793
_exptl_crystal_F_000             2912
_refine_diff_density_max         0.763
_refine_diff_density_min         -1.262
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.213
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4539
_reflns_number_total             5920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00551a2.cif
_cod_data_source_block           aks52
_cod_depositor_comments
;
          Adding full bibliography for 7159953.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H I N O S'
_cod_original_formula_weight         201.99
_cod_original_formula_moiety         '0.13(C28 H23 I2 N O5 S)'
_cod_original_formula_units_Z            32
_cod_database_code               7159953
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O S I'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L), C00N(H00N),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C010(H010)
2.d Idealised Me refined as rotating group:
 C00Z(H00D,H00E,H00H), C011(H01A,H01B,H01C)
;
_shelx_res_checksum              70132
_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 1.746
_oxdiff_exptl_absorpt_empirical_full_min 0.667