“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_7220410
_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_absolute_configuration ad
_chemical_formula_sum            'C13 H11 N3 O5'
_chemical_formula_weight         289.25
_chemical_name_systematic
3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-03 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.60650(10)
_cell_length_b                   7.18580(10)
_cell_length_c                   11.1840(2)
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.53
_cell_volume                     645.794(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4451
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_coef       0.059(7)
_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   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.0485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2751
_reflns_number_total             2841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5gc00503e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7220410--7220412.cif.
;
_cod_original_cell_volume        645.794(16)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7220410