Synthesis of 1′-tetrazolylmethyl-spiro[pyrrolidine-3,3′-oxindoles] via two coupled one-pot processes Ugi-azide/Pictet–Spengler and oxidative spiro-rearrangement
Alvarez-Rodríguez, Nancy V.; Islas-Jácome, Alejandro; Rentería-Gómez, Angel; Cárdenas-Galindo, Luis E.; Unnamatla, M. V. Basavanag; Gámez-Montaño, Rocío; New Journal of Chemistry 42 (2018) 1600–; doi:10.1039/C7NJ03829A

data_7056843
_publ_section_title
;
 Synthesis of
 1&#x2032;-tetrazolylmethyl-spiro[pyrrolidine-3,3&#x2032;-oxindoles] via
 two coupled one-pot processes Ugi-azide/Pictet--Spengler and oxidative
 spiro-rearrangement
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1600
_journal_paper_doi               10.1039/C7NJ03829A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C20 H20 N6 O'
_chemical_formula_sum            'C20 H20 N6 O'
_chemical_formula_weight         360.42
_chemical_melting_point          202.0(10)
_chemical_name_systematic
1'-((1-benzyl-1H-tetrazol-5-yl)methyl)spiro[indoline-3,3'-pyrrolidin]-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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_block_doi                 10.5517/ccdc.csd.cc1p0sq6
_audit_creation_date             2015-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-13 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.585(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3115(8)
_cell_length_b                   6.3966(2)
_cell_length_c                   18.3592(9)
_cell_measurement_reflns_used    9584
_cell_measurement_temperature    298.5
_cell_measurement_theta_max      26.3680
_cell_measurement_theta_min      3.7640
_cell_volume                     1890.43(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.5
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0945
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9110
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details
;
  1 omega    1.00   83.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000   90.0000 82

  2 omega    0.00   70.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000 -180.0000 70

  3 omega   28.00   54.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000  -90.0000 26

  4 omega   40.00   74.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000 -150.0000 34

  5 omega   -2.00   34.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000    0.0000 36

  6 omega  -20.00   55.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000   30.0000 75

  7 omega   -3.00   85.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   37.0000   30.0000 88

  8 omega   35.00   88.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  178.0000  -30.0000 53

  9 omega  -11.00   83.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   77.0000 -120.0000 94

 10 omega  -11.00   60.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070 -109.0000 -159.0000 71

 11 omega  -53.00   35.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -37.0000  -90.0000 88

 12 omega  -85.00   -1.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -      -17.5258  -57.0000  150.0000 84

 13 omega  -47.00    6.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -      -17.5258   19.0000  150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0325706000
_diffrn_orient_matrix_UB_12      -0.0034728000
_diffrn_orient_matrix_UB_13      -0.0146922000
_diffrn_orient_matrix_UB_21      -0.0291084000
_diffrn_orient_matrix_UB_22      -0.0253401000
_diffrn_orient_matrix_UB_23      -0.0377249000
_diffrn_orient_matrix_UB_31      -0.0057861000
_diffrn_orient_matrix_UB_32      0.1079002000
_diffrn_orient_matrix_UB_33      -0.0093346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34648
_diffrn_reflns_theta_full        29.6320
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_min         3.40
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.2663
_exptl_crystal_F_000             760.2807
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hex-AcOEt (1/1 v/v)'
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.8362
_refine_diff_density_min         -0.3046
_refine_diff_density_rms         0.0729
_refine_ls_d_res_high            0.7187
_refine_ls_d_res_low             5.9899
_refine_ls_goodness_of_fit_ref   1.0505
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0505
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0976P)^2^+1.5727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2298
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -23
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3554
_reflns_number_total             4822
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7nj03829a2.cif
_cod_data_source_block           UMV_14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '201-203' was changed to '202.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7056843--7056844.cif.
;
_cod_database_code               7056843
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.71
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C20(H20a,H20b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C22(H22), C23(H23), C24(H24), C26(H26)
;
_olex2_date_sample_data_collection 2015-08-25
_olex2_submission_original_sample_id UMV14
_olex2_submission_special_instructions 'No special instructions were received'