“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_7220411
_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_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.33
_chemical_name_systematic
3-(1-(3-ethyl-4-nitroisoxazol-5-yl)ethyl)-3-hydroxy-5-methoxyindolin-2-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.7630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5271(6)
_cell_length_b                   7.4112(3)
_cell_length_c                   16.5010(8)
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.73
_cell_measurement_theta_min      3.33
_cell_volume                     1648.55(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10871
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             728
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0049(15)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0828P)^2^+0.2502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                2006
_reflns_number_total             3768
_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_sg_symbol_H-M      P2(1)/n
_cod_database_code               7220411