Multicomponent One-Pot Synthesis of 3-Tetrazolyl and 3-Imidazo[1,2-a]pyridin Tetrazolo[1,5-a]quinolines.
Unnamatla, M. V. Basavanag; Islas-Jácome, Alejandro; Quezada-Soto, Andrea; Ramírez-López, Sandra C; Flores-Álamo, Marcos; Gámez-Montaño, Rocío; The Journal of organic chemistry 81 (2016) 10576–10583; doi:10.1021/acs.joc.6b01576

data_4037135
_publ_section_title
;
 Multicomponent One-Pot Synthesis of 3-Tetrazolyl and
 3-Imidazo[1,2-a]pyridin Tetrazolo[1,5-a]quinolines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10576
_journal_page_last               10583
_journal_paper_doi               10.1021/acs.joc.6b01576
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H21 N9'
_chemical_formula_sum            'C21 H21 N9'
_chemical_formula_weight         399.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-19
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.633(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.7679(4)
_cell_length_b                   9.58691(17)
_cell_length_c                   23.2936(5)
_cell_measurement_reflns_used    12653
_cell_measurement_temperature    294
_cell_measurement_theta_max      77.2410
_cell_measurement_theta_min      3.9040
_cell_volume                     4466.19(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
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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    'olex2.solve (Bourhis et al., 2015)'
_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    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000 -150.0000 82

  2 omega  -50.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000  -60.0000 82

  3 omega -119.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -77.0000 -180.0000 109

  4 omega  -90.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  110.0000  -70.0000 106

  5 omega  -50.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000  120.0000 82

  6 omega  -50.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   38.0000  -90.0000 82

  7 omega  -48.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824   32.0000   80.0000 81

  8 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -120.0000 80

  9 omega   38.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  120.0000 53

 10 omega   38.00  147.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000 -120.0000 109

 11 omega   86.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000  -30.0000 92

 12 omega   38.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -180.0000 53

 13 omega   38.00  147.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000   90.0000 109

 14 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000   60.0000 80

 15 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  150.0000 80

 16 omega   88.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -90.0000 90

 17 omega   41.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000    0.0000 57

 18 omega   88.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000    0.0000 90

 19 omega   41.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 57

 20 omega   41.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000   90.0000 57

 21 omega   41.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -60.0000 57

 22 omega   38.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 53

 23 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  -60.0000 80

 24 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  -90.0000 80

 25 omega   41.00  121.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  120.0000 80

 26 omega   88.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   30.0000 90

 27 omega   31.00  109.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -60.0000 78

 28 omega   94.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  125.0000  -90.0000 84

 29 omega   61.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000   90.0000 117

 30 omega -119.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -77.0000  -90.0000 109

 31 omega -115.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -57.0000  -30.0000 101

 32 omega -115.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -57.0000   60.0000 101

 33 omega -115.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.4824  -57.0000 -120.0000 101

 34 omega   10.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4824   77.0000  120.0000 109

 35 omega   -4.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       42.4824  -99.0000  120.0000 87

 36 omega   61.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000 -150.0000 117

 37 omega   81.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000 -180.0000 97

 38 omega   81.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000 -150.0000 97

 39 omega   81.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000   90.0000 97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0498504000
_diffrn_orient_matrix_UB_12      0.0743287000
_diffrn_orient_matrix_UB_13      0.0281083000
_diffrn_orient_matrix_UB_21      0.0378209000
_diffrn_orient_matrix_UB_22      0.1383729000
_diffrn_orient_matrix_UB_23      0.0003113000
_diffrn_orient_matrix_UB_31      -0.0449332000
_diffrn_orient_matrix_UB_32      0.0339660000
_diffrn_orient_matrix_UB_33      -0.0626511000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46439
_diffrn_reflns_theta_full        77.69
_diffrn_reflns_theta_max         77.69
_diffrn_reflns_theta_min         3.94
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86410
_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_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00020(6)
_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   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0481
_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^)+(0.1030P)^2^+0.6020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                3909
_reflns_number_total             4746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1b.cif
_cod_data_source_block           srl269_qusa012_1
_cod_original_cell_volume        4466.22(15)
_cod_database_code               4037135
_chemical_oxdiff_formula         C20H20N9
_chemical_oxdiff_usercomment     '0.22 X 0.18 X 0.20'
_reflns_odcompleteness_completeness 99.98
_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) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'