Gold-catalyzed dual annulation of azide-tethered alkynes with nitriles: expeditious synthesis of oxazolo[4,5-c]quinolines
Su, Han; Bao, Ming; Pei, Chao; Hu, Wenhao; Qiu, Lihua; Xu, Xinfang; Organic Chemistry Frontiers 6 (2019) 2404–; doi:10.1039/C9QO00568D

data_1554947
_publ_section_title
;
 Gold-catalyzed dual annulation of azide-tethered alkynes with nitriles:
 expeditious synthesis of oxazolo[4,5-c]quinolines
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2404
_journal_paper_doi               10.1039/C9QO00568D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C25 H15 N3 O'
_chemical_formula_sum            'C25 H15 N3 O'
_chemical_formula_weight         373.42
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
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Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
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_audit_update_record
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2019-03-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
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_cell_angle_alpha                90
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
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_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details
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  1 omega  -66.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.4965  -77.0000   90.0000 109

  2 omega  -14.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.4965   38.0000  -90.0000 85

  3 omega  -22.00   10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2778  -99.0000   30.0000 32

  4 omega  -50.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2778   19.0000   60.0000 105
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_33      -0.0478371000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_theta_full        26.3722
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_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60676
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_density_diffrn    1.3362
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_exptl_crystal_F_000             776.3214
_exptl_crystal_size_max          0.62
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_constraints    30
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_refine_ls_restrained_S_all      1.0655
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0468
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_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.2642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_limit_l_min              -7
_reflns_number_gt                2608
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_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9qo00568d2.cif
_cod_data_source_block           G190327A
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1554947
_chemical_oxdiff_formula         CHON
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C5(H5), C4(H4), C3(H3), C2(H2),
 C1(H1), C25(H25), C24(H24), C23(H23), C22(H22), C21(H21), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'