An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core.
Eltyshev, Alexander K.; Suntsova, Polina O.; Karmatskaia, Ksenia D.; Taniya, Olga S.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.; Organic & biomolecular chemistry 16 (2018) 9420–9429; doi:10.1039/c8ob02644k

data_7156584
_publ_section_title
;
 An effective and facile synthesis of new blue fluorophores on the basis
 of an 8-azapurine core.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9420
_journal_page_last               9429
_journal_paper_doi               10.1039/c8ob02644k
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H22 N6 O2'
_chemical_formula_sum            'C22 H22 N6 O2'
_chemical_formula_weight         402.45
_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'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2018-07-30 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.5416(13)
_cell_length_b                   5.9720(4)
_cell_length_c                   15.4401(15)
_cell_measurement_reflns_used    1086
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.3310
_cell_measurement_theta_min      3.5410
_cell_volume                     1986.3(3)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
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 0.9989
_diffrn_measured_fraction_theta_max 0.6059
_diffrn_measurement_details
;
  1 omega  -50.00   67.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -19.0000 -150.0000 117

  2 omega   58.00   98.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360 -178.0000  -90.0000 40
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0269709000
_diffrn_orient_matrix_UB_12      0.0329901000
_diffrn_orient_matrix_UB_13      -0.0230735000
_diffrn_orient_matrix_UB_21      0.0175990000
_diffrn_orient_matrix_UB_22      0.0058841000
_diffrn_orient_matrix_UB_23      -0.0387394000
_diffrn_orient_matrix_UB_31      -0.0069021000
_diffrn_orient_matrix_UB_32      -0.1139618000
_diffrn_orient_matrix_UB_33      -0.0086894000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6843
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.71
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91684
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                1605
_reflns_number_total             2840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02644k2.cif
_cod_data_source_block           exp_848
_cod_depositor_comments
;
Adding full bibliography for 7156583--7156584.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C22 H22 N6 O2)'
_cod_original_formula_sum        'C44 H44 N12 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     804.91
_cod_database_code               7156584
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22