Synthesis of substituted oxazoles via Pd-catalyzed tandem oxidative cyclization
Zhang, Wei; Yu, Wenlong; Yan, Qiangqiang; Liu, Zhanxiang; Zhang, Yuhong; Organic Chemistry Frontiers 4 (2017) 2428–; doi:10.1039/C7QO00517B

data_1553836
_publ_section_title
;
 Synthesis of substituted oxazoles via Pd-catalyzed tandem oxidative
 cyclization
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2428
_journal_paper_doi               10.1039/C7QO00517B
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H15 N O'
_chemical_formula_sum            'C16 H15 N O'
_chemical_formula_weight         237.29
_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     direct
_audit_creation_date             2017-05-09
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_audit_update_record
;
2017-05-11 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.737(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9086(8)
_cell_length_b                   9.5831(7)
_cell_length_c                   19.453(2)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.2230
_cell_measurement_theta_min      3.2589
_cell_volume                     1279.0(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -61.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000 -180.0000 89

  2 omega  -67.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000  -30.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0441016000
_diffrn_orient_matrix_UB_12      -0.0385219000
_diffrn_orient_matrix_UB_13      -0.0251234000
_diffrn_orient_matrix_UB_21      -0.0791602000
_diffrn_orient_matrix_UB_22      0.0168501000
_diffrn_orient_matrix_UB_23      -0.0252537000
_diffrn_orient_matrix_UB_31      0.0497467000
_diffrn_orient_matrix_UB_32      0.0609612000
_diffrn_orient_matrix_UB_33      -0.0088610000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5057
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.265
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.333
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.333
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.1365
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3471
_refine_ls_wR_factor_ref         0.3583
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.601
_reflns_Friedel_fraction_max     0.598
_reflns_number_gt                3115
_reflns_number_total             3782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00517b2.cif
_cod_data_source_block           170509_zw2_005_3_1
_cod_database_code               1553836
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.53
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), N2(H2A), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              12082
_shelx_hkl_checksum              88559
_olex2_submission_special_instructions 'No special instructions were received'