Synthesis and Fluorescent Behaviour of 2-Aryl-4,5-dihydro-1H-1,2,4-triazoles.
Eliseeva, Alexandra I.; Nesterenko, Olga O.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.; The Journal of organic chemistry 82 (2017) 86–100; doi:10.1021/acs.joc.6b02144

data_4032238
_publ_section_title
;
 Synthesis and Fluorescent Behaviour of
 2-Aryl-4,5-dihydro-1H-1,2,4-triazoles.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              86
_journal_page_last               100
_journal_paper_doi               10.1021/acs.joc.6b02144
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C17 H18 N4 O5'
_chemical_formula_sum            'C17 H18 N4 O5'
_chemical_formula_weight         358.35
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-21
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                82.712(4)
_cell_angle_beta                 86.457(4)
_cell_angle_gamma                86.322(4)
_cell_formula_units_Z            4
_cell_length_a                   8.0289(3)
_cell_length_b                   10.1511(5)
_cell_length_c                   22.4007(12)
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1010
_cell_measurement_theta_min      2.4810
_cell_volume                     1804.57(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9800
_diffrn_measured_fraction_theta_max 0.8575
_diffrn_measurement_details
;
  1 omega  -22.00    5.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000   90.0000 27

  2 omega  -24.00   14.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000  -30.0000 38

  3 omega   -2.00   90.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   38.0000    0.0000 92

  4 omega    2.00   92.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000   90.0000 90

  5 omega  -23.00   62.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -       23.2924  -99.0000 -180.0000 85

  6 omega  -43.00   32.00   1.0000   18.2800
omega____ theta____ kappa____ phi______ frames
    -       23.2924  -38.0000 -180.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0198895000
_diffrn_orient_matrix_UB_12      0.0155801000
_diffrn_orient_matrix_UB_13      0.0286183000
_diffrn_orient_matrix_UB_21      0.0188226000
_diffrn_orient_matrix_UB_22      0.0650621000
_diffrn_orient_matrix_UB_23      -0.0130787000
_diffrn_orient_matrix_UB_31      -0.0843212000
_diffrn_orient_matrix_UB_32      0.0224180000
_diffrn_orient_matrix_UB_33      0.0056533000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16879
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_min         1.84
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'greenish yellow'
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         9589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.2027
_reflns_number_gt                5764
_reflns_number_total             9589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02144_si_002.cif
_cod_data_source_block           exp_802
_cod_original_cell_volume        1804.56(15)
_cod_database_code               4032238
_reflns_odcompleteness_completeness 98.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22