“On water” direct catalytic vinylogous Henry (nitroaldol) reactions of isatins for the efficient synthesis of isoxazole substituted 3-hydroxyindolin-2-ones
Zhang, Yong; Wei, Biao-Wen; Lin, Hui; Zhang, Ling; Liu, Jin-Xiang; Luo, Hai-Qing; Fan, Xiao-Lin; Green Chem. 17 (2015) 3266–; doi:10.1039/C5GC00503E

data_7220412
_publ_section_title
;
 &#x201C;On water&#x201D; direct catalytic vinylogous Henry (nitroaldol)
 reactions of isatins for the efficient synthesis of isoxazole substituted
 3-hydroxyindolin-2-ones
;
_journal_issue                   6
_journal_name_full               'Green Chem.'
_journal_page_first              3266
_journal_paper_doi               10.1039/C5GC00503E
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C13 H13 N3 O3'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26
_chemical_name_systematic
3-((4-amino-3-methylisoxazol-5-yl)methyl)-3-hydroxyindolin-2-one
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-01
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2015-02-03 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.537(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3186(4)
_cell_length_b                   11.7574(8)
_cell_length_c                   16.3886(12)
_cell_measurement_reflns_used    569
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      23.8730
_cell_measurement_theta_min      3.9770
_cell_volume                     1211.83(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   65.00   95.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -90.0000 20

  2 omega   29.00   89.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946    0.0000 -180.0000 40

  3 omega  -33.00   90.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946    0.0000  120.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1005160000
_diffrn_orient_matrix_UB_12      -0.0239132000
_diffrn_orient_matrix_UB_13      -0.0058745000
_diffrn_orient_matrix_UB_21      -0.0125508000
_diffrn_orient_matrix_UB_22      0.0169727000
_diffrn_orient_matrix_UB_23      -0.0417086000
_diffrn_orient_matrix_UB_31      0.0497096000
_diffrn_orient_matrix_UB_32      0.0526830000
_diffrn_orient_matrix_UB_33      0.0108001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.466
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1277
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5gc00503e2.cif
_cod_data_source_block           matq1120
_cod_depositor_comments
'Adding full bibliography for 7220410--7220412.cif.'
_cod_original_cell_volume        1211.84(14)
_cod_database_code               7220412
_reflns_odcompleteness_completeness 99.77
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2C), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 1416533413.32
_olex2_submission_special_instructions 'No special instructions were received'