Synthesis, characterization and photophysical studies of dual-emissive base-modified fluorescent nucleosides.
Arora, Aditi; Kumar, Sumit; Kumar, Sandeep; Dua, Amita; Singh, Brajendra K.; Organic & biomolecular chemistry 22 (2024) 4922–4939; doi:10.1039/d4ob00749b

data_7159958
_publ_section_title
;
 Synthesis, characterization and photophysical studies of dual-emissive
 base-modified fluorescent nucleosides.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4922
_journal_page_last               4939
_journal_paper_doi               10.1039/d4ob00749b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 N4 O3'
_chemical_formula_sum            'C18 H14 N4 O3'
_chemical_formula_weight         334.33
_chemical_name_systematic
4-(azidomethyl)-N9-phenyl-9,10-dihydro-2H,8H-chromeno[8,7-e][1,3]oxazin-2-one
_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     dual
_audit_creation_date             2023-12-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.777(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1867(6)
_cell_length_b                   14.9870(6)
_cell_length_c                   8.0323(4)
_cell_measurement_reflns_used    8289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3060
_cell_measurement_theta_min      3.2960
_cell_volume                     1568.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.824
_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    -23.00  27.00   0.50   10.47    --   -5.68 -99.00   0.00  100
  2  \w    -23.00  27.00   0.50   10.47    --   -5.68 -99.00 -30.00  100
  3  \w    -28.00  67.00   0.50   10.47    --   -5.68  77.00 -30.00  190
  4  \w    -23.00  38.00   0.50   10.47    --    5.83 -99.00-180.00  122
  5  \w    -81.00  -5.00   0.50   10.47    --   -5.68 -19.00-120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0421740000
_diffrn_orient_matrix_UB_12      0.0228589000
_diffrn_orient_matrix_UB_13      -0.0466832000
_diffrn_orient_matrix_UB_21      -0.0297594000
_diffrn_orient_matrix_UB_22      -0.0395313000
_diffrn_orient_matrix_UB_23      -0.0030844000
_diffrn_orient_matrix_UB_31      -0.0172858000
_diffrn_orient_matrix_UB_32      0.0124049000
_diffrn_orient_matrix_UB_33      0.0761358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18230
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.046
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_preparation
'Slow evaporation in methaol and chloroform mixture'
_exptl_crystal_recrystallization_method Evaporation
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.1447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2829
_reflns_number_total             4134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00749b2.cif
_cod_data_source_block           akp-a-6171_auto
_cod_depositor_comments          'Adding full bibliography for 7159958.cif.'
_cod_database_code               7159958
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O H'
_chemical_oxdiff_usercomment     02.12.2022
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C16(H16), C6(H6), C12(H12), C15(H15), C14(H14), C13(H13)
;
_shelx_res_checksum              2140
_olex2_submission_original_sample_id AKP-A-6171
_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 1.652
_oxdiff_exptl_absorpt_empirical_full_min 0.597