Electrochemical assembly of isoxazoles <i>via</i> a four-component domino reaction.
Zhao, Yuanyuan; Li, Xinyue; Homölle, Simon L; Wang, Bin; Ackermann, Lutz; Chemical science 15 (2024) 1117–1122; doi:10.1039/d3sc05946d

data_1570533
_publ_section_title
;
 Electrochemical assembly of isoxazoles <i>via</i> a four-component domino
 reaction.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1117
_journal_page_last               1122
_journal_paper_doi               10.1039/d3sc05946d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C20 H18 N2 O'
_chemical_formula_sum            'C20 H18 N2 O'
_chemical_formula_weight         302.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6595(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.00483(6)
_cell_length_b                   7.13118(10)
_cell_length_c                   37.8376(4)
_cell_measurement_reflns_used    6546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0700
_cell_measurement_theta_min      4.6800
_cell_volume                     1619.58(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4337
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.957
_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    -86.00 -61.00   0.50    2.00    --  -41.76 -38.00 -90.00   50
  2  \w    -83.00 -21.00   0.50    2.00    --  -41.76 -38.00 -30.00  124
  3  \w    -76.00  -7.00   0.50    2.00    --  -41.76 125.00-150.00  138
  4  \w   -114.00 -15.00   0.50    2.00    --  -41.76 -57.00 -90.00  198
  5  \w    -49.00 -23.00   0.50    2.00    --  -41.76 -57.00 -30.00   52
  6  \w    -20.00  62.00   0.50    2.00    --   41.76 -77.00 150.00  164
  7  \w    103.00 165.00   0.50    4.00    --  106.05  77.00  90.00  124
  8  \w     23.00  97.00   0.50    4.00    --  106.05 -94.00  60.00  148
  9  \w     78.00 104.00   0.50    4.00    --  106.05  61.00 -46.01   52
 10  \w     77.00 116.00   0.50    4.00    --  106.05  61.00   0.00   78
 11  \w    125.00 176.00   0.50    4.00    --  106.05  61.00   0.00  102
 12  \w     77.00 169.00   0.50    4.00    --  106.05  61.00  60.00  184
 13  \w     78.00 127.00   0.50    4.00    --  106.05  61.00 -90.00   98
 14  \w     77.00 103.00   0.50    4.00    --  106.05  61.00 -30.00   52
 15  \w    111.00 178.00   0.50    4.00    --  106.05  70.00 -72.77  134
 16  \w     83.00 109.00   0.50    4.00    --  106.05  45.00   0.00   52
 17  \w     85.00 112.00   0.50    4.00    --  106.05  45.00 -60.00   54
 18  \w    102.00 157.00   0.50    4.00    --  106.05 125.00 120.00  110
 19  \w     77.00 103.00   0.50    4.00    --  106.05  61.00  30.00   52
 20  \w    127.00 173.00   0.50    4.00    --  106.05  61.00 -30.00   92
 21  \w     82.00 112.00   0.50    4.00    --  106.05  45.00  60.00   60
 22  \w     80.00  89.00   0.50    4.00    --  106.05  45.00  30.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2320389000
_diffrn_orient_matrix_UB_12      0.0568064000
_diffrn_orient_matrix_UB_13      -0.0126526000
_diffrn_orient_matrix_UB_21      -0.0830209000
_diffrn_orient_matrix_UB_22      -0.0202017000
_diffrn_orient_matrix_UB_23      -0.0387256000
_diffrn_orient_matrix_UB_31      -0.0716630000
_diffrn_orient_matrix_UB_32      0.2074049000
_diffrn_orient_matrix_UB_33      -0.0002906000
_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  0.0131
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            10118
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.976
_diffrn_reflns_theta_min         4.677
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.2295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2907
_reflns_number_total             3111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05946d2.cif
_cod_data_source_block           221127_auto
_cod_depositor_comments          'Adding full bibliography for 1570533.cif.'
_cod_database_code               1570533
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.878
_reflns_odcompleteness_completeness 97.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C8(H8), C3(H3), C12(H12), C11(H11), C2(H2), C5(H5), C6(H6)
1.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              93491
_shelx_hkl_checksum              5248
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.678