Asmic Isocyanide [3 + 2] Cascade to Dihydrooxazoles and Dihydroimidazoles.
Kumar, Chepuri V Suneel; Holyoke, Jr, Caleb W; Keller, Taylor M.; Fleming, Fraser F.; The Journal of organic chemistry 85 (2020) 9153–9160; doi:10.1021/acs.joc.0c01119

data_4038564
_publ_section_title
;
 Asmic Isocyanide [3 + 2] Cascade to Dihydrooxazoles and
 Dihydroimidazoles.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9153
_journal_page_last               9160
_journal_paper_doi               10.1021/acs.joc.0c01119
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C25 H23 N3 O5 S2'
_chemical_formula_sum            'C25 H23 N3 O5 S2'
_chemical_formula_weight         509.58
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-17
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2960(10)
_cell_angle_gamma                90
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_cell_length_a                   14.6337(10)
_cell_length_b                   8.2120(6)
_cell_length_c                   19.9944(14)
_cell_measurement_reflns_used    9160
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.58
_cell_volume                     2392.5(3)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'COSMO (Bruker AXS)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29898
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.086
_diffrn_reflns_theta_min         1.397
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7456
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_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0458 before and 0.0339 after correction. The Ratio of minimum to maximum transmission is 0.9396. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0328P)^2^+1.1661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0742
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5385
_reflns_number_total             5797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01119_si_002.cif
_cod_data_source_block           solve
_cod_depositor_comments          'Adding full bibliography for 4038564.cif.'
_cod_database_code               4038564
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.918
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              30832
_shelx_hkl_checksum              21863
_olex2_submission_special_instructions 'No special instructions were received'