Chemodivergent C-to-N atom swap from benzofurans to benzisoxazoles and benzoxazoles
Paschke, Ann-Sophie K.; Schiele, Stefanie; Pinard, Camille; Sandrini, Filippo; Morandi, Bill; Chemical Science 16 (2025) 11464–11467; doi:10.1039/D5SC02032H

data_1574728
_publ_section_title
;
 Chemodivergent C-to-N atom swap from benzofurans to benzisoxazoles and
 benzoxazoles
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              11464
_journal_page_last               11467
_journal_paper_doi               10.1039/D5SC02032H
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_chemical_name_systematic        'methyl benzo[d]isoxazole-5-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-21 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.043(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4696(3)
_cell_length_b                   11.1571(3)
_cell_length_c                   7.1041(2)
_cell_measurement_reflns_used    8797
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.4290
_cell_measurement_theta_min      3.9520
_cell_volume                     789.03(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.966
_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     28.00 100.00   0.50    0.10    --   67.93-140.00  66.00  144
  2  \w     31.00 103.00   0.50    0.10    --   70.78-140.00  66.00  144
  3  \w     38.00 109.00   0.50    0.40    --   77.85-140.00  66.00  142
  4  \w     38.00 109.00   0.50    0.40    --   77.85-140.00  66.00  142
  5  \w     75.00 100.00   0.50    0.40    --   77.85-125.00 -30.00   50
  6  \w     33.00  59.00   0.50    0.40    --   77.85-125.00 -30.00   52
  7  \w     25.00  96.00   0.50    0.10    --   67.93-130.00-119.00  142
  8  \w     28.00  99.00   0.50    0.10    --   70.78-130.00-119.00  142
  9  \w     46.00  98.00   0.50    0.40    --   77.85-125.00-150.00  104
 10  \w     69.00 100.00   0.50    0.40    --   77.85-125.00-120.00   62
 11  \w     35.00 102.00   0.50    0.40    --   77.85-130.00-119.00  134
 12  \w     37.00  94.00   0.50    0.40    --   77.85-125.00 -90.00  114
 13  \w     37.00  84.00   0.50    0.40    --   77.85 -95.00 -90.00   94
 14  \w     44.00  83.00   0.50    0.40    --   77.85 -95.00-120.00   78
 15  \w     27.00  76.00   0.50    0.10    --   67.93 -95.00 -60.00   98
 16  \w     48.00  83.00   0.50    0.40    --   77.85 -95.00 -30.00   70
 17  \w     74.00 100.00   0.50    0.40    --   77.85-125.00   0.00   52
 18  \w     41.00  84.00   0.50    0.40    --   77.85 -95.00  90.00   86
 19  \w     81.00 113.00   0.50    0.10    --   72.89  16.00  24.62   64
 20  \w     92.00 118.00   0.50    0.40    --   75.17  23.00 -84.51   52
 21  \w     91.00 116.00   0.50    0.10    --   72.89  27.00-173.13   50
 22  \w     82.00 112.00   0.50    0.10    --   72.89  17.00  -6.31   60
 23  \w     61.00  92.00   0.50    0.10    --   46.00  53.00  66.92   62
 24  \w     91.00 116.00   0.50    0.40    --   75.17  22.00  94.16   50
 25  \w     91.00 116.00   0.50    0.40    --   75.17  20.00 161.44   50
 26  \w    -92.00 -61.00   0.50    0.10    --  -46.00 -53.00 119.50   62
 27  \w   -112.00 -81.00   0.50    0.10    --  -66.00 -53.00 152.25   62
 28  \w   -106.00 -72.00   0.50    0.10    --  -58.00 -45.00  90.97   68
 29  \w   -117.00 -85.00   0.50    0.10    --  -70.00 -38.00 175.70   64
 30  \w   -118.00 -84.00   0.50    0.10    --  -70.00 -45.00  67.50   68
 31  \w   -120.00 -91.00   0.50    0.10    --  -74.00 -31.00  85.84   58
 32  \w   -108.00 -80.00   0.50    0.10    --  -62.00 -33.00  17.87   56
 33  \w   -119.00 -94.00   0.50    0.40    --  -75.17 -27.00   2.57   50
 34  \w   -110.00 -76.00   0.50    0.10    --  -62.00 -45.00 -60.34   68
 35  \w   -105.00 -74.00   0.50    0.10    --  -58.00 -39.00-103.69   62
 36  \w   -112.00 -87.00   0.50    0.10    --  -70.00 -25.00-170.39   50
 37  \w   -101.00 -69.00   0.50    0.10    --  -54.00 -48.00-140.62   64
 38  \w   -114.00 -88.00   0.50    0.10    --  -72.64 -20.00-117.19   52
 39  \w   -114.00 -88.00   0.50    0.40    --  -75.17 -15.00-118.38   52
 40  \w   -110.00 -84.00   0.50    0.10    --  -70.00 -20.00-143.05   52
 41  \w   -118.00 -91.00   0.50    0.40    --  -75.17 -23.00  51.35   54
 42  \w   -117.00 -92.00   0.50    0.40    --  -75.17 -22.00 174.26   50
 43  \w   -111.00 -86.00   0.50    0.10    --  -70.00 -20.00 110.27   50
 44  \w    -63.00 -36.00   0.50    0.10    --  -72.64  75.00 107.86   54
 45  \w    -57.00 -32.00   0.50    0.10    --  -72.64  70.00 153.47   50
 46  \w    -35.00  -8.00   0.50    0.10    --  -54.00  52.00  67.08   54
 47  \w    -63.00 -38.00   0.50    0.10    --  -72.64  72.00  57.28   50
 48  \w    -98.00 -26.00   0.50    0.10    --  -66.25 140.00 125.00  144
 49  \w   -102.00 -29.00   0.50    0.10    --  -69.39 140.00 125.00  146
 50  \w    -95.00 -25.00   0.50    0.10    --  -69.39 125.00  30.00  140
 51  \w    -63.00 -31.00   0.50    0.40    --  -75.17 125.00   4.14   64
 52  \w    -99.00 -61.00   0.50    0.40    --  -75.17 121.00  -5.02   76
 53  \w    -95.00 -69.00   0.50    0.40    --  -75.17 125.00   4.14   52
 54  \w    -94.00 -23.00   0.50    0.10    --  -66.25 130.00 -47.00  142
 55  \w    -97.00 -26.00   0.50    0.10    --  -69.39 130.00 -47.00  142
 56  \w    -96.00 -68.00   0.50    0.40    --  -75.17 117.00-127.02   56
 57  \w    -62.00 -35.00   0.50    0.40    --  -75.17 115.00 -52.10   54
 58  \w    -99.00 -72.00   0.50    0.40    --  -75.17 121.00 -29.51   54
 59  \w    -95.00 -69.00   0.50    0.40    --  -75.17 115.00 -52.10   52
 60  \w    -68.00 -35.00   0.50    0.10    --  -72.64  99.00 -54.02   66
 61  \w    -64.00 -38.00   0.50    0.10    --  -72.64  84.00-120.13   52
 62  \w    -98.00 -72.00   0.50    0.40    --  -75.17 121.00  58.90   52
 63  \w    -57.00 -30.00   0.50    0.40    --  -75.17 121.00  58.90   54
 64  \w    -92.00 -51.00   0.50    0.10    --  -72.64 116.00 109.30   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1390867000
_diffrn_orient_matrix_UB_12      0.0146745000
_diffrn_orient_matrix_UB_13      -0.0286075000
_diffrn_orient_matrix_UB_21      0.0177816000
_diffrn_orient_matrix_UB_22      -0.1372090000
_diffrn_orient_matrix_UB_23      0.0068293000
_diffrn_orient_matrix_UB_31      -0.0653697000
_diffrn_orient_matrix_UB_32      -0.0059381000
_diffrn_orient_matrix_UB_33      -0.2261690000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14398
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         4.442
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.039
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0637P)^2^+0.2086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1380
_reflns_number_total             1556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02032h2.cif
_cod_data_source_block           bm291124_1_1
_cod_depositor_comments
'Adding full bibliography for 1574726--1574728.cif.'
_cod_original_cell_volume        789.02(4)
_cod_database_code               1574728
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C9H7NO3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.816
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              93878
_olex2_date_sample_data_collection 2024-11-26
_olex2_date_sample_submission    2024-11-26
_olex2_submission_original_sample_id bm291124_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.355