Phosphine-catalyzed dearomative [3+2] cycloaddition of 4-nitroisoxazoles with allenoates or Morita-Baylis-Hillman carbonates.
He, Yongjun; He, Tian-Juan; Cheng, Xiufang; Wei, Yibo; Wang, Huamin; Lin, Ying-Wu; Chemical communications (Cambridge, England) 60 (2024) 6961–6964; doi:10.1039/d4cc02231a

data_7133179
_publ_section_title
;
 Phosphine-catalyzed dearomative [3+2] cycloaddition of 4-nitroisoxazoles
 with allenoates or Morita-Baylis-Hillman carbonates.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6961
_journal_page_last               6964
_journal_paper_doi               10.1039/d4cc02231a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 N4 O5 S'
_chemical_formula_sum            'C15 H12 N4 O5 S'
_chemical_formula_weight         360.35
_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             2024-02-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-04-05 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0981(5)
_cell_length_b                   11.5834(4)
_cell_length_c                   10.0872(4)
_cell_measurement_reflns_used    9067
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.743
_cell_measurement_theta_min      2.983
_cell_volume                     1505.85(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31277
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.745
_diffrn_reflns_theta_min         2.983
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1302 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.8662.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0444P)^2^+0.7444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3256
_reflns_number_total             3420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02231a2.cif
_cod_data_source_block           240228_nwj_1
_cod_depositor_comments
'Adding full bibliography for 7133178--7133179.cif.'
_cod_database_code               7133179
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.809
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              88886
_shelx_hkl_checksum              70363
_olex2_submission_special_instructions 'No special instructions were received'