Luminescent pyrenyl-GNA nucleosides: synthesis, photophysics and confocal microscopy studies in cancer HeLa cells.
Skiba, Joanna; Kowalczyk, Aleksandra; Fik, Marta A.; Gapińska, Magdalena; Trzybiński, Damian; Woźniak, Krzysztof; Vrček, Valerije; Czerwieniec, Rafał; Kowalski, Konrad; Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 18 (2019) 2449–2460; doi:10.1039/c9pp00271e

data_1552223
_publ_section_title
;
 Luminescent pyrenyl-GNA nucleosides: synthesis, photophysics and confocal
 microscopy studies in cancer HeLa cells.
;
_journal_issue                   10
_journal_name_full
'Photochemical &amp; photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              2449
_journal_page_last               2460
_journal_paper_doi               10.1039/c9pp00271e
_journal_volume                  18
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2019-03-11 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.896(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4331(2)
_cell_length_b                   8.9471(3)
_cell_length_c                   26.8786(9)
_cell_measurement_reflns_used    4950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.8990
_cell_measurement_theta_min      3.2980
_cell_volume                     1781.03(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1134882000
_diffrn_orient_matrix_UB_12      -0.1104741000
_diffrn_orient_matrix_UB_13      -0.0336334000
_diffrn_orient_matrix_UB_21      -0.0282123000
_diffrn_orient_matrix_UB_22      0.1210364000
_diffrn_orient_matrix_UB_23      -0.0406454000
_diffrn_orient_matrix_UB_31      0.1719465000
_diffrn_orient_matrix_UB_32      -0.0530063000
_diffrn_orient_matrix_UB_33      -0.0229415000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.301
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.357
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0760P)^2^+0.5329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9pp00271e2.cif
_cod_data_source_block           2018_03_27_dt_js-385_n
_cod_depositor_comments          'Adding full bibliography for 1552223.cif.'
_cod_original_cell_volume        1781.03(9)
_cod_database_code               1552223
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N22-H22
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C13(H13), C17(H17), C25(H25), C6(H6), C11(H11), C14(H14),
 C10(H10), C18(H18), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.725