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_4037137
_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 Cl N6'
_chemical_formula_sum            'C21 H21 Cl N6'
_chemical_formula_weight         392.89
_chemical_name_systematic
N-((1-(tert-butyl)-1H-tetrazol-5-yl)(2-chloroquinolin-3-yl)methyl)aniline
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.181(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8431(7)
_cell_length_b                   16.1181(9)
_cell_length_c                   10.8078(5)
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4390
_cell_measurement_theta_min      3.5390
_cell_volume                     2059.90(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.9768
_diffrn_measured_fraction_theta_max 0.8189
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -83.00 -38.00   1.00   35.30    --  -17.53-178.00 -60.00   45
  2  \w    -89.00   9.00   1.00   35.30    --  -17.53 -19.00-120.00   98
  3  \w    -58.00   5.00   1.00   35.30    --  -17.53 -19.00 120.00   63
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205005000
_diffrn_orient_matrix_UB_12      -0.0344529000
_diffrn_orient_matrix_UB_13      -0.0353520000
_diffrn_orient_matrix_UB_21      -0.0535476000
_diffrn_orient_matrix_UB_22      0.0194866000
_diffrn_orient_matrix_UB_23      -0.0083770000
_diffrn_orient_matrix_UB_31      0.0175032000
_diffrn_orient_matrix_UB_32      0.0192705000
_diffrn_orient_matrix_UB_33      -0.0547865000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9483
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.52
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.2668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824.8446
_exptl_crystal_recrystallization_method
'crystalised in dueterated chloroform in nmr tube'
_exptl_crystal_size_max          0.631
_exptl_crystal_size_mid          0.603
_exptl_crystal_size_min          0.533
_refine_diff_density_max         0.2429
_refine_diff_density_min         -0.3730
_refine_diff_density_rms         0.0515
_refine_ls_d_res_high            0.7212
_refine_ls_d_res_low             5.9124
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0335
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0335
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.4234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3445
_reflns_number_total             4702
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            6b.cif
_cod_data_source_block           exp_233
_cod_original_cell_volume        2059.88(19)
_cod_database_code               4037137
_chemical_oxdiff_formula         C21H21ClN6
_reflns_odcompleteness_completeness 96.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C22(H22), C26(H26), C28(H28)
;
_olex2_date_sample_data_collection 2016-03-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.874