A sequential direct arylation/Suzuki-Miyaura cross-coupling transformation of unprotected 2'-deoxyadenosine affords a novel class of fluorescent analogues.
Storr, Thomas E.; Strohmeier, Johanna A.; Baumann, Christoph G.; Fairlamb, Ian J. S.; Chemical communications (Cambridge, England) 46 (2010) 6470–6472; doi:10.1039/c0cc02043e

data_7112795
_publ_section_title
;
 A sequential direct arylation/Suzuki-Miyaura cross-coupling
 transformation of unprotected 2'-deoxyadenosine affords a novel class of
 fluorescent analogues.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6470
_journal_page_last               6472
_journal_paper_doi               10.1039/c0cc02043e
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         '4(C24 H23 N5 O4), 5(C H4 O), H2 O'
_chemical_formula_sum            'C25.25 H28.5 N5 O5.5'
_chemical_formula_weight         490.03
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.783(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.5839(14)
_cell_length_b                   29.990(3)
_cell_length_c                   13.3097(15)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.18
_cell_volume                     4964.1(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_max       16
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_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            67955
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10; (Sheldrick)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2072
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.071
_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   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1304
_refine_ls_number_reflns         12574
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0995P)^2^+2.7717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                10787
_reflns_number_total             12574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc02043e.txt
_cod_data_source_block           ijf1001m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        4964.0(10)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7112795