Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic (PASE) synthesis, mechanistic insight and fluorescence properties
Sadchikova, Elena V.; Beliaev, Nikolai A.; Alexeeva, Daria L.; Safronov, Nikita E.; Belskaya, Nataliya P.; New Journal of Chemistry 46 (2022) 22171–22184; doi:10.1039/D2NJ04085A

data_7062114
_publ_section_title
;
 Non-aromatic azolo[5,1-c][1,2,4]triazines: a pot, atom and step economic
 (PASE) synthesis, mechanistic insight and fluorescence properties
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22171
_journal_page_last               22184
_journal_paper_doi               10.1039/D2NJ04085A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C12.75 H14.25 N7 O4 S, 0.25(C H3)'
_chemical_formula_sum            'C13 H15 N7 O4 S'
_chemical_formula_weight         365.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-09
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2022-06-07 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.275(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.226(3)
_cell_length_b                   12.3104(11)
_cell_length_c                   7.2437(11)
_cell_measurement_reflns_used    825
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.6700
_cell_measurement_theta_min      2.7940
_cell_volume                     1608.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_details
;
  1 omega  -12.00   18.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000 -120.0000 30

  2 omega    2.00   87.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   57.0000  120.0000 85

  3 omega    8.00   88.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   38.0000   30.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0282635000
_diffrn_orient_matrix_UB_12      0.0101190000
_diffrn_orient_matrix_UB_13      0.0557749000
_diffrn_orient_matrix_UB_21      -0.0259943000
_diffrn_orient_matrix_UB_22      0.0080101000
_diffrn_orient_matrix_UB_23      -0.0816128000
_diffrn_orient_matrix_UB_31      -0.0087636000
_diffrn_orient_matrix_UB_32      -0.0561150000
_diffrn_orient_matrix_UB_33      -0.0016590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5855
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0650P)^2^+0.0450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                1893
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj04085a2.cif
_cod_data_source_block           exp_788
_cod_database_code               7062114
_reflns_odcompleteness_completeness 80.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22