An Unusual Formal Migrative Cycloaddition of Aurone-derived Azadienes: Synthesis of Benzofuran-fused Nitrogen Heterocycles
Feng, Qiang; Wu, An; Zhang, Xinhao; Song, Lijuan; Sun, Jianwei; Chemical Science  (2021) –; doi:10.1039/D1SC00941A

data_1562380
_publ_section_title
;
 An Unusual Formal Migrative Cycloaddition of Aurone-derived Azadienes:
 Synthesis of Benzofuran-fused Nitrogen Heterocycles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC00941A
_journal_year                    2021
_chemical_formula_moiety         'C28 H25 Br Cl N O4 S'
_chemical_formula_sum            'C28 H25 Br Cl N O4 S'
_chemical_formula_weight         586.91
_chemical_name_systematic
'Trans-3-Bromo-3-butyl-2-(4-chlorophenyl)-1-tosyl-2,3-dihydrobenzofuro [3,2-b]pyridin-4(1H)-one'
_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             2021-02-18
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-21 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                78.442(4)
_cell_angle_beta                 65.815(4)
_cell_angle_gamma                79.502(4)
_cell_formula_units_Z            2
_cell_length_a                   10.7962(5)
_cell_length_b                   10.9702(4)
_cell_length_c                   11.8384(5)
_cell_measurement_reflns_used    6217
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      76.4630
_cell_measurement_theta_min      4.1500
_cell_volume                     1245.21(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.955
_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   -129.00  49.00   1.00    1.00    --  -39.95   0.00 -60.00  178
  2  \w     28.00  55.00   1.00    1.00    --   39.95-125.00  60.00   27
  3  \w     30.00  76.00   1.00    1.00    --   39.95-125.00 -30.00   46
  4  \w     32.00  59.00   1.00    1.00    --   39.95-125.00-120.00   27
  5  \w     27.00  85.00   1.00    1.00    --   39.95-125.00 150.00   58
  6  \w     71.00 109.00   1.00    2.00    --  113.00-111.00 120.00   38
  7  \w     40.00 140.00   1.00    2.00    --  113.00 -61.00-150.00  100
  8  \w     87.00 175.00   1.00    2.00    --  113.00  30.00 -60.00   88
  9  \w    142.00 168.00   1.00    2.00    --  113.00  30.00 150.00   26
 10  \w     84.00 120.00   1.00    2.00    --  113.00  30.00 150.00   36
 11  \w     36.00  82.00   1.00    2.00    --  113.00-111.00  90.00   46
 12  \w     40.00  66.00   1.00    2.00    --  113.00-111.00 120.00   26
 13  \w     90.00 178.00   1.00    2.00    --  113.00  45.00-180.00   88
 14  \w     65.00 109.00   1.00    2.00    --  113.00-111.00-120.00   44
 15  \w     35.00 107.00   1.00    2.00    --  113.00-111.00  30.00   72
 16  \w     98.00 175.00   1.00    2.00    --  113.00  45.00-120.00   77
 17  \w     40.00 143.00   1.00    2.00    --  113.00 -61.00  90.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0997724000
_diffrn_orient_matrix_UB_12      0.0515198000
_diffrn_orient_matrix_UB_13      -0.0657079000
_diffrn_orient_matrix_UB_21      -0.0778680000
_diffrn_orient_matrix_UB_22      -0.1159095000
_diffrn_orient_matrix_UB_23      0.0623230000
_diffrn_orient_matrix_UB_31      -0.0936027000
_diffrn_orient_matrix_UB_32      0.0686855000
_diffrn_orient_matrix_UB_33      0.1120534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7889
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.815
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0229
_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^)+(0.0313P)^2^+0.5439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4803
_reflns_number_total             5020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00941a2.cif
_cod_data_source_block           qf19cult
_cod_database_code               1562380
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Cl C20 H18 O4 N'
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.478
_reflns_odcompleteness_completeness 98.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              16922
_shelx_hkl_checksum              15325
_olex2_date_sample_data_collection 2021-02-17
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.857