Photophysics, photochemistry and bioimaging application of 8-azapurine derivatives.
Eltyshev, Alexander K.; Agafonova, Irina A.; Minin, Artem S.; Pozdina, Varvara A.; Shevirin, Vadim A.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.; Organic & biomolecular chemistry 19 (2021) 9880–9896; doi:10.1039/d1ob01801a

data_7158337
_publ_section_title
;
 Photophysics, photochemistry and bioimaging application of 8-azapurine
 derivatives.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9880
_journal_page_last               9896
_journal_paper_doi               10.1039/d1ob01801a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C16 H17 Cl3 N6 O2'
_chemical_formula_sum            'C16 H17 Cl3 N6 O2'
_chemical_formula_weight         431.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.790(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1174(6)
_cell_length_b                   18.2984(12)
_cell_length_c                   12.9072(8)
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.8970
_cell_measurement_theta_min      3.7160
_cell_volume                     1876.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.965
_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     31.00  56.00   1.00   60.00    --   22.36-152.00 162.00   25
  2  \w     12.00  37.00   1.00   60.00    --   22.36-122.00 -37.00   25
  3  \w    -79.00 -33.00   1.00   60.00    --  -23.92 122.00  44.00   46
  4  \w    -76.00 -39.00   1.00   60.00    --  -23.92 152.00-155.00   37
  5  \w    -96.00   2.00   1.00   60.00    --  -23.92 -38.00  90.00   98
  6  \w    -93.00  -3.00   1.00   60.00    --  -23.92 -57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0056139000
_diffrn_orient_matrix_UB_12      0.0384750000
_diffrn_orient_matrix_UB_13      -0.0048292000
_diffrn_orient_matrix_UB_21      0.0382407000
_diffrn_orient_matrix_UB_22      0.0025012000
_diffrn_orient_matrix_UB_23      0.0544271000
_diffrn_orient_matrix_UB_31      0.0805008000
_diffrn_orient_matrix_UB_32      -0.0038700000
_diffrn_orient_matrix_UB_33      -0.0128336000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12805
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
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    1.528
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3163
_reflns_number_total             4875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01801a2.cif
_cod_data_source_block           exp_933
_cod_depositor_comments
'Adding full bibliography for 7158337--7158338.cif.'
_cod_database_code               7158337
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.802
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              34360
_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 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.937