InCl<sub>3</sub>-catalyzed 5-exo-dig cyclization/1,6-conjugate addition of N-propargylamides with p-QMs to construct oxazole derivatives.
Nan, Guang-Ming; Li, Xue; Yao, Tian-Yu; Yan, Ting-Xun; Wen, Li-Rong; Li, Ming; Organic & biomolecular chemistry 18 (2020) 1780–1784; doi:10.1039/c9ob02651g

data_7157348
_publ_section_title
;
 InCl<sub>3</sub>-catalyzed 5-exo-dig cyclization/1,6-conjugate addition
 of N-propargylamides with p-QMs to construct oxazole derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1780
_journal_page_last               1784
_journal_paper_doi               10.1039/c9ob02651g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C32 H36 Br N O3'
_chemical_formula_sum            'C32 H36 Br N O3'
_chemical_formula_weight         562.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-16 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                79.59(3)
_cell_angle_beta                 67.45(2)
_cell_angle_gamma                60.750(14)
_cell_formula_units_Z            2
_cell_length_a                   11.157(3)
_cell_length_b                   11.335(4)
_cell_length_c                   13.795(4)
_cell_measurement_reflns_used    4007
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4708
_cell_measurement_theta_min      1.5984
_cell_volume                     1405.7(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19581
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.418
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0640
_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^)+(0.0268P)^2^+1.2747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5333
_reflns_number_total             6349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02651g2.cif
_cod_data_source_block           mx6274c
_cod_depositor_comments
;Adding full bibliography for 7157348.cif.

 Adding full bibliography for 7157348.cif.
;
_cod_original_cell_volume        1405.6(7)
_cod_database_code               7157348
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.781
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21), C25(H25), C28(H28),
 C29(H29), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              19099
_olex2_submission_special_instructions 'No special instructions were received'