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_7056844
_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         'C21 H23 N6'
_chemical_formula_sum            'C21 H23 N6'
_chemical_formula_weight         359.45
_chemical_melting_point          468.0(10)
_chemical_name_systematic
2-((1-(2,6-dimethylphenyl)-1H-tetrazol-5-yl)methyl)-2,3,4,9-tetrahydro-1H-2l4-pyrido[3,4-b]indole
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1p0wq9
_audit_creation_date             2015-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-05-13 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.201(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.22814(16)
_cell_length_b                   32.2130(5)
_cell_length_c                   7.46549(15)
_cell_measurement_reflns_used    11899
_cell_measurement_temperature    294
_cell_measurement_theta_max      76.6070
_cell_measurement_theta_min      4.0610
_cell_volume                     1868.67(6)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000   30.0000 82

  2 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000 -120.0000 82

  3 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000   60.0000 82

  4 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000  120.0000 82

  5 omega -117.00  -18.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -38.0000   30.0000 99

  6 omega -115.00  -60.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574 -146.0000  163.0000 55

  7 omega   57.00  131.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -       42.3574  178.0000    0.0000 74

  8 omega   -4.00   83.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -       42.3574  -99.0000   60.0000 87

  9 omega   94.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  125.0000 -180.0000 84

 10 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -120.0000 78

 11 omega   38.00   91.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  120.0000 53

 12 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 78

 13 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000 -120.0000 92

 14 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000   30.0000 80

 15 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -120.0000 80

 16 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000  -60.0000 92

 17 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -60.0000 78

 18 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  150.0000 80

 19 omega   38.00   91.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 53

 20 omega   88.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -30.0000 90

 21 omega   41.00   98.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -90.0000 57

 22 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -180.0000 80

 23 omega   42.00  143.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -180.0000 101

 24 omega   41.00   98.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000    0.0000 57

 25 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -180.0000 78

 26 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000    0.0000 78

 27 omega   85.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -180.0000 93

 28 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  -90.0000 109

 29 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000 -150.0000 82

 30 omega -115.00  -14.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -57.0000  150.0000 101

 31 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  -30.0000 109

 32 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  150.0000 109

 33 omega -115.00  -14.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -57.0000  -60.0000 101

 34 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000 -180.0000 109

 35 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000   60.0000 109

 36 omega   85.00  172.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -120.0000 87

 37 omega   85.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000   90.0000 93

 38 omega   81.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000   30.0000 97

 39 omega   88.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 90

 40 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000   30.0000 92

 41 omega   61.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000  120.0000 117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0273632000
_diffrn_orient_matrix_UB_12      0.0471783000
_diffrn_orient_matrix_UB_13      -0.0286497000
_diffrn_orient_matrix_UB_21      0.1949068000
_diffrn_orient_matrix_UB_22      0.0070549000
_diffrn_orient_matrix_UB_23      0.0930786000
_diffrn_orient_matrix_UB_31      0.0238822000
_diffrn_orient_matrix_UB_32      -0.0035312000
_diffrn_orient_matrix_UB_33      -0.1955799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            39099
_diffrn_reflns_theta_full        77.54
_diffrn_reflns_theta_max         77.54
_diffrn_reflns_theta_min         5.49
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80224
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             764
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hex-AcOEt (7/3 v/v)'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0003(2)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0724P)^2^+0.5077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                3450
_reflns_number_total             3980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7nj03829a2.cif
_cod_data_source_block           srl272-na160
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '467-469' was changed to '468.0(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               7056844
_chemical_oxdiff_formula         'C21 H22 N6'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C22(H22), C23(H23), C24(H24), N11(H11)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_olex2_exptl_crystal_mounting_method 'mounted on a glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'