Synthesis of 7-Aza-5-deazapurine Analogues via Copper(I)-Catalyzed Hydroamination of Alkynes and 1-Iodoalkynes
Larissa B. Krasnova; Jason E. Hein; Valery V. Fokin; Journal of Organic Chemistry 75 (2010) 8662–8665; doi:10.1021/jo1016376

data_4025864
_publ_section_title
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 Synthesis of 7-Aza-5-deazapurine Analogues via Copper(I)-Catalyzed
 Hydroamination of Alkynes and 1-Iodoalkynes
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8662
_journal_page_last               8665
_journal_paper_doi               10.1021/jo1016376
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C14 H18 I N5 O5 S'
_chemical_formula_weight         495.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.485(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5727(12)
_cell_length_b                   13.436(3)
_cell_length_c                   23.627(5)
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.28
_cell_volume                     1767.4(7)
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.896
_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
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10117
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.09
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  0.9080
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0290P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                2733
_reflns_number_total             3862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1016376_si_003.cif
_cod_data_source_block           sharp30
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4025864