Biocatalytic one-pot three-component synthesis of 3,3’-disubstituted oxindoles and spirooxindole pyrans using α-amylase from hog pancreas
He, Tao; Zeng, Qingqing; yang, Dacheng; He, Yanhong; Guan, Zhi; RSC Adv.  (2015) –; doi:10.1039/C4RA16825A

data_7220213
_publ_section_title
;
 Biocatalytic one-pot three-component synthesis of
 3,3&#x2019;-disubstituted oxindoles and spirooxindole pyrans using
 \a-amylase from hog pancreas
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA16825A
_journal_year                    2015
_chemical_formula_moiety         'C17 H15 N3 O3'
_chemical_formula_sum            'C17 H15 N3 O3'
_chemical_formula_weight         307.30
_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             2015-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-03-13 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.9160(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.82662(14)
_cell_length_b                   27.6395(4)
_cell_length_c                   13.1668(2)
_cell_measurement_reflns_used    12705
_cell_measurement_temperature    288.02(10)
_cell_measurement_theta_max      71.2920
_cell_measurement_theta_min      4.7260
_cell_volume                     3089.08(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      288.02(10)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega    1.00   76.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -99.0000   30.0000 75

  2 omega  -32.00   56.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -38.0000    0.0000 88

  3 omega    1.00   76.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -99.0000   90.0000 75

  4 omega    1.00   27.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   93.0000 -156.5327 26

  5 omega    1.00   27.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   93.0000   14.0788 26

  6 omega   10.00  105.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   77.0000 -150.0000 95

  7 omega   10.00  105.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   77.0000  -60.0000 95

  8 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   90.0000 71

 10 omega   38.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  -90.0000 78

 11 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 12 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 14 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 15 omega  101.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  112.0000 -180.0000 77

 16 omega   40.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

 17 omega   57.00  109.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  178.0000  -30.0000 52

 18 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000  120.0000 88

 19 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000 -180.0000 88

 20 omega   57.00  109.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  178.0000   30.0000 52

 21 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000   60.0000 88

 22 omega   70.00  147.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 77

 23 omega   70.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0684500000
_diffrn_orient_matrix_UB_12      0.0511154000
_diffrn_orient_matrix_UB_13      -0.0024506000
_diffrn_orient_matrix_UB_21      0.1385551000
_diffrn_orient_matrix_UB_22      -0.0215413000
_diffrn_orient_matrix_UB_23      -0.0351201000
_diffrn_orient_matrix_UB_31      -0.0951987000
_diffrn_orient_matrix_UB_32      0.0054013000
_diffrn_orient_matrix_UB_33      -0.1164610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.498
_diffrn_reflns_theta_min         4.737
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.603
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_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0605P)^2^+2.5454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5585
_reflns_number_total             5944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra16825a2.cif
_cod_data_source_block           gz050305
_cod_depositor_comments
;

2017-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H15 N3 O3)'
_cod_original_formula_sum        'C34 H26 N6 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     614.61
_cod_database_code               7220213
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C5(H5), C28(H28), C29(H29), C31(H31), C30(H30)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C17(H17A,H17B,H17C), C44(H44A,H44B,
 H44C), C40(H40A,H40B,H40C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              3043
_shelx_hkl_checksum              39418
_olex2_submission_special_instructions 'No special instructions were received'