Organocatalytic Asymmetric Domino Aza-Michael-Mannich Reaction: Synthesis of Tetrahydroimidazopyrimidine Derivatives
Hong Li; Junling Zhao; Lili Zeng; Wenhui Hu; Journal of Organic Chemistry 76 (2011) 8064–8069; doi:10.1021/jo201301p

data_4026611
_publ_section_title
;
 Organocatalytic Asymmetric Domino Aza-Michael-Mannich Reaction: Synthesis
 of Tetrahydroimidazopyrimidine Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8064
_journal_page_last               8069
_journal_paper_doi               10.1021/jo201301p
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H17 N3 O S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C17.5 H18 Cl N3 O S'
_chemical_formula_weight         353.86
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-04-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.3403(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5962(2)
_cell_length_b                   9.71266(13)
_cell_length_c                   14.3697(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1779.27(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?

_refine_special_details
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22091
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.062
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.5130
_exptl_crystal_size_mid          0.2559
_exptl_crystal_size_min          0.1162
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0557
_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^)+(0.1355P)^2^+0.1287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                5825
_reflns_number_total             6239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201301p_si_001.cif
_cod_data_source_block           d
_cod_original_cell_volume        1779.26(5)
_cod_original_formula_sum        'C17.50 H18 Cl N3 O S'
_cod_database_code               4026611