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_4032239
_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         'C16 H18 Cl N3 O5'
_chemical_formula_sum            'C16 H18 Cl N3 O5'
_chemical_formula_weight         367.78
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-11
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.563(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4037(6)
_cell_length_b                   8.6319(4)
_cell_length_c                   19.9954(14)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0540
_cell_measurement_theta_min      2.5810
_cell_volume                     1793.86(18)
_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 0.9994
_diffrn_measured_fraction_theta_max 0.8795
_diffrn_measurement_details
;
  1 omega  -18.00   17.00   1.0000   90.5000
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000  -30.0000 35

  2 omega    6.00   87.00   1.0000   90.5000
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000 -150.0000 81

  3 omega  -20.00   96.00   1.0000   90.5000
omega____ theta____ kappa____ phi______ frames
    -       23.2924   19.0000  -30.0000 116
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0462840000
_diffrn_orient_matrix_UB_12      0.0037579000
_diffrn_orient_matrix_UB_13      0.0270974000
_diffrn_orient_matrix_UB_21      0.0484483000
_diffrn_orient_matrix_UB_22      -0.0245846000
_diffrn_orient_matrix_UB_23      -0.0214891000
_diffrn_orient_matrix_UB_31      0.0129527000
_diffrn_orient_matrix_UB_32      0.0783173000
_diffrn_orient_matrix_UB_33      -0.0080579000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9099
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.74
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90288
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0039(11)
_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   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                2088
_reflns_number_total             4888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02144_si_002.cif
_cod_data_source_block           exp_910
_cod_original_cell_volume        1793.86(19)
_cod_database_code               4032239
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22