Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones.
An, Hejun; Mai, Shaoyu; Xuan, Qingqing; Zhou, Yao; Song, Qiuling; The Journal of organic chemistry 84 (2019) 401–408; doi:10.1021/acs.joc.8b02334

data_4035913
_publ_section_title
;
 Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal
 N-Propargylamides for the Construction of 5-Oxazole Ketones.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              401
_journal_page_last               408
_journal_paper_doi               10.1021/acs.joc.8b02334
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 Cl N O2'
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         282.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4505(6)
_cell_length_b                   11.2690(9)
_cell_length_c                   31.662(2)
_cell_measurement_reflns_used    1127
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.6300
_cell_measurement_theta_min      3.8010
_cell_volume                     2658.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_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    -39.00  25.20   0.30    1.00    --   15.65 -19.00   0.00  214
  2  \w      5.00  48.20   0.30    1.00    --  -16.28  57.00 150.00  144
  3  \w    -20.00  11.20   0.30    1.00    --  -16.28 -99.00 120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205745000
_diffrn_orient_matrix_UB_12      -0.0586437000
_diffrn_orient_matrix_UB_13      -0.0065514000
_diffrn_orient_matrix_UB_21      0.0215005000
_diffrn_orient_matrix_UB_22      0.0213462000
_diffrn_orient_matrix_UB_23      -0.0204585000
_diffrn_orient_matrix_UB_31      0.0904128000
_diffrn_orient_matrix_UB_32      0.0082367000
_diffrn_orient_matrix_UB_33      0.0063621000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            7098
_diffrn_reflns_theta_full        24.9937
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.4177
_exptl_crystal_description       block
_exptl_crystal_F_000             1169.7173
_refine_diff_density_max         0.3543
_refine_diff_density_min         -0.5740
_refine_diff_density_rms         0.1492
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             6.0986
_refine_ls_goodness_of_fit_ref   0.9801
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9801
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1690
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                1583
_reflns_number_total             2329
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b02334_si_002.cif
_cod_data_source_block           exp_5353
_cod_depositor_comments
;

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2658.3(4)
_cod_original_formula_moiety     '0.67(C16 H10 Cl N O2)'
_cod_original_formula_sum        'C10.667 H6.667 Cl0.667 N0.667 O1.333'
_cod_original_formula_units_Z    12
_cod_original_formula_weight     189.14
_cod_database_code               4035913
_reflns_odcompleteness_completeness 99.37
_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:
 C00J(H00J), C00E(H00E), C00D(H00D), C00H(H00H), C00B(H00B), C00I(H00I),
 C00G(H00G), C00A(H00A), C005(H005), C00F(H00F)
;
_olex2_date_sample_data_collection 2018-04-23
_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 1.351
_oxdiff_exptl_absorpt_empirical_full_min 0.527