A practical base mediated synthesis of 1,2,4-triazoles enabled by a deamination annulation strategy.
Zhang, Chunyan; Liang, Zuyu; Jia, Xiaofei; Wang, Maorong; Zhang, Guoying; Hu, Mao-Lin; Chemical communications (Cambridge, England) 56 (2020) 14215–14218; doi:10.1039/d0cc05828a

data_7127418
_publ_section_title
;
 A practical base mediated synthesis of 1,2,4-triazoles enabled by a
 deamination annulation strategy.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14215
_journal_page_last               14218
_journal_paper_doi               10.1039/d0cc05828a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration s
_chemical_formula_moiety         'C18 H13 N5'
_chemical_formula_sum            'C18 H13 N5'
_chemical_formula_weight         299.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-11 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6944(3)
_cell_length_b                   5.09040(10)
_cell_length_c                   15.1667(2)
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4840
_cell_measurement_theta_min      4.7290
_cell_volume                     1443.29(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_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    -58.00 -25.00   0.50    0.05    --  -43.18 -59.00 -30.00   66
  2  \w    -94.00 -68.00   0.50    0.05    --  -43.18 -59.00 -30.00   52
  3  \w    -71.00 -16.00   0.50    0.05    --  -90.25  65.00 -99.00  110
  4  \w    -71.00  29.00   0.50    0.05    --  -43.18  77.00 120.00  200
  5  \w     62.00  93.00   0.50    0.05    --   43.18-125.00 150.00   62
  6  \w     55.00 123.00   0.50    0.05    --  109.88 -59.00 -30.00  136
  7  \w     71.00  99.00   0.50    0.05    --  109.88-108.00-113.00   56
  8  \w     38.00  99.00   0.50    0.05    --  109.88 -94.00 -60.00  122
  9  \w    137.00 178.00   0.50    0.05    --  109.88  45.00 150.00   82
 10  \w     89.00 119.00   0.50    0.05    --  109.88  45.00 150.00   60
 11  \w    100.00 129.00   0.50    0.05    --  109.88  61.00-120.00   58
 12  \w    133.00 174.00   0.50    0.05    --  109.88  61.00-120.00   82
 13  \w     42.00  79.00   0.50    0.05    --  109.88 -65.00 125.00   74
 14  \w     64.00  97.00   0.50    0.05    --   43.18-125.00-120.00   66
 15  \w   -106.00 -80.00   0.50    0.05    --  -90.25 -94.00-180.00   52
 16  \w   -153.00-124.00   0.50    0.05    --  -90.25 -94.00-180.00   58
 17  \w    147.00 173.00   0.50    0.05    --  109.88 125.00-120.00   52
 18  \w     94.00 128.00   0.50    0.05    --  109.88 125.00-120.00   68
 19  \w     47.00  99.00   0.50    0.05    --  109.88 -94.00 -30.00  104
 20  \w    146.00 178.00   0.50    0.05    --  109.88  30.00  30.00   64
 21  \w     98.00 123.00   0.50    0.05    --  109.88 -65.00 125.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0605375000
_diffrn_orient_matrix_UB_12      -0.1633994000
_diffrn_orient_matrix_UB_13      -0.0415101000
_diffrn_orient_matrix_UB_21      -0.0137835000
_diffrn_orient_matrix_UB_22      -0.1333262000
_diffrn_orient_matrix_UB_23      0.0896394000
_diffrn_orient_matrix_UB_31      -0.0541831000
_diffrn_orient_matrix_UB_32      0.2170002000
_diffrn_orient_matrix_UB_33      0.0237265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6732
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         4.731
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0638P)^2^+0.1526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2302
_reflns_number_total             2350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05828a2.cif
_cod_data_source_block           exp_3225
_cod_depositor_comments          'Adding full bibliography for 7127418.cif.'
_cod_database_code               7127418
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N)
;
_shelx_res_checksum              35621
_shelx_hkl_checksum              25635
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.299