Copper-catalyzed Annulation Reaction of Alkenes and N-alkyl(aryl)-1- (methylthio)-2-nitroethenamine: an Approach for the Synthesis of Isoxazole Derivatives.
Pan, Zhengbing; Mao, Kaimin; Zhu, Guangzhou; Wang, Chang; Zhang, Jinpeng; Rong, Liangce; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03157

data_4037948
_publ_section_title
;
 Copper-catalyzed Annulation Reaction of Alkenes and N-alkyl(aryl)-1-
 (methylthio)-2-nitroethenamine: an Approach for the Synthesis of
 Isoxazole Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03157
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 N3 O4'
_chemical_formula_sum            'C12 H13 N3 O4'
_chemical_formula_weight         263.25
_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             2018-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.609(4)
_cell_angle_beta                 93.905(4)
_cell_angle_gamma                91.966(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7970(4)
_cell_length_b                   8.5423(4)
_cell_length_c                   9.3211(4)
_cell_measurement_reflns_used    3731
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      28.4890
_cell_measurement_theta_min      3.0640
_cell_volume                     614.71(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -60.00  40.00   1.00    1.00    --   11.90 -57.00  60.00  100
  2  \w    -21.00  88.00   1.00    1.00    --   11.90  77.00 -30.00  109
  3  \w    -16.00  85.00   1.00    1.00    --   11.90  57.00-150.00  101
  4  \w     34.00  99.00   1.00    1.00    --   11.90-178.00  60.00   65
  5  \w    -16.00  31.00   1.00    1.00    --   11.90  57.00  90.00   47
  6  \w    -20.00  53.00   1.00    1.00    --   11.90 -99.00-120.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0749221000
_diffrn_orient_matrix_UB_12      -0.0254212000
_diffrn_orient_matrix_UB_13      -0.0452708000
_diffrn_orient_matrix_UB_21      -0.0471191000
_diffrn_orient_matrix_UB_22      -0.0040825000
_diffrn_orient_matrix_UB_23      0.0620225000
_diffrn_orient_matrix_UB_31      -0.0222639000
_diffrn_orient_matrix_UB_32      0.0796045000
_diffrn_orient_matrix_UB_33      -0.0017693000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0492P)^2^+0.1980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1870
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03157_si_002.cif
_cod_data_source_block           3_0711
_cod_database_code               4037948
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C4(H4), C2(H2), C3(H3A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;
_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 1.973
_oxdiff_exptl_absorpt_empirical_full_min 0.624