Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- and 2'-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties.
Leonard, Peter; Kondhare, Dasharath; Jentgens, Xenia; Daniliuc, Constantin; Seela, Frank; The Journal of organic chemistry 84 (2019) 13313–13328; doi:10.1021/acs.joc.9b01347

data_4033630
_publ_section_title
;
 Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- and
 2'-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and
 Photophysical Properties.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13313
_journal_page_last               13328
_journal_paper_doi               10.1021/acs.joc.9b01347
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H12 I N5 O4'
_chemical_formula_weight         393.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                90
_cell_angle_beta                 96.6740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9620(2)
_cell_length_b                   13.1568(6)
_cell_length_c                   10.7648(5)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      70.1151
_cell_measurement_theta_min      4.1348
_cell_volume                     698.01(5)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11870
_diffrn_reflns_theta_full        70.14
_diffrn_reflns_theta_max         70.14
_diffrn_reflns_theta_min         4.13
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    18.248
_exptl_absorpt_correction_T_max  0.42
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.512
_refine_ls_abs_structure_details
;

Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.069(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0199
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+0.9670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0478
_reflns_number_gt                2462
_reflns_number_total             2493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01347_si_002.cif
_cod_data_source_block           dan9407
_cod_depositor_comments          'Adding full bibliography for 4033630.cif.'
_cod_database_code               4033630
_shelx_res_checksum              84715
_shelx_hkl_checksum              43365
_shelx_fab_checksum              77698