Tetramethylsuccinimide as a directing/protecting group in purine glycosylations.
Arico, Joseph W.; Calhoun, Amy K.; Salandria, Kerry J.; McLaughlin, Larry W.; Organic letters 12 (2010) 120–122; doi:10.1021/ol9025028

data_1503342
_publ_section_title
;
 Tetramethylsuccinimide as a directing/protecting group in purine
 glycosylations.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              120
_journal_page_last               122
_journal_paper_doi               10.1021/ol9025028
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         '(C13 H16 N5 O2)+ Cl-'
_chemical_formula_sum            'C13 H16 Cl N5 O2'
_chemical_formula_weight         309.76
_chemical_melting_point          ?
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.395(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.705(8)
_cell_length_b                   7.976(4)
_cell_length_c                   12.332(7)
_cell_measurement_reflns_used    6204
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.81
_cell_volume                     1427.0(13)
_computing_cell_refinement       'SMART, SAINT'
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXP-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXCIF-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3411
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       cube
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0509P)^2^+1.3039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                2820
_reflns_number_total             3411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9025028_si_001.cif
_cod_data_source_block           C13H16ClN5O2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503342