Endogenous water-triggered and ultrasound accelerated synthesis of 1,5-disubstituted tetrazoles via a solvent and catalyst-free Ugi-azide reaction
Pharande, Shrikant G.; Corrales Escobosa, Alma Rosa; Gámez-Montaño, Rocío; Green Chem. 19 (2017) 1259–; doi:10.1039/C6GC03324E

data_7227453
_publ_section_title
;
 Endogenous water-triggered and ultrasound accelerated synthesis of
 1,5-disubstituted tetrazoles via a solvent and catalyst-free Ugi-azide
 reaction
;
_journal_issue                   5
_journal_name_full               'Green Chem.'
_journal_page_first              1259
_journal_paper_doi               10.1039/C6GC03324E
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C22 H21 N5'
_chemical_formula_sum            'C22 H21 N5'
_chemical_formula_weight         355.44
_chemical_melting_point          409
_chemical_name_systematic
N-((1-(2,6-dimethylphenyl)-1H-tetrazol-5-yl)(phenyl)methyl)aniline
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                86.787(4)
_cell_angle_beta                 75.671(4)
_cell_angle_gamma                82.064(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2637(4)
_cell_length_b                   10.3529(4)
_cell_length_c                   10.4849(5)
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.3300
_cell_measurement_theta_min      3.8080
_cell_volume                     964.70(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0945
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.819
_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     -3.00  74.10   0.30   11.76    --   15.81  37.00 -90.00  257
  2  \w     -9.00  79.50   0.30   11.76    --   15.81  77.00 -90.00  295
  3  \w     -9.00  82.20   0.30   11.76    --   15.81  77.00 120.00  304
  4  \w    -44.00  20.20   0.30   11.76    --  -17.84  77.00   0.00  214
  5  \w    -60.00 -35.10   0.30   11.76    --  -17.84 178.00 -30.00   83
  6  \w    -51.00 -21.90   0.30   11.76    --   15.81 -77.00   0.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0226539000
_diffrn_orient_matrix_UB_12      0.0196499000
_diffrn_orient_matrix_UB_13      -0.0587566000
_diffrn_orient_matrix_UB_21      -0.0544771000
_diffrn_orient_matrix_UB_22      0.0489028000
_diffrn_orient_matrix_UB_23      0.0347926000
_diffrn_orient_matrix_UB_31      0.0535615000
_diffrn_orient_matrix_UB_32      0.0448336000
_diffrn_orient_matrix_UB_33      -0.0146557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8194
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.563
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Compound was recristalized by using DCM:Hexane (1:1 V/V)'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0512P)^2^+0.2061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3323
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6gc03324e2.cif
_cod_data_source_block           exp_333
_cod_depositor_comments          'Adding full bibliography for 7227453.cif.'
_cod_original_cell_volume        964.70(8)
_cod_database_code               7227453
_chemical_oxdiff_formula         'C N O H'
_chemical_oxdiff_usercomment     Rocio
_reflns_odcompleteness_completeness 99.70
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C11(H11), C13(H13), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27(H27A,H27B,H27C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-09-08
_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 0.768