Two novel diastereoselective three-component reactions of alkenes or 3,4-dihydro-(2H)-pyran with urea/thiourea-aldehyde mixtures: [4 + 2] cycloaddition vs Biginelli-type reaction.
Zhu, Yulin; Huang, Shenlin; Wan, Jieping; Yan, Lei; Pan, Yuanjiang; Wu, Anxin; Organic letters 8 (2006) 2599–2602; doi:10.1021/ol060874b

data_1506026
_publ_section_title
;
 Two novel diastereoselective three-component reactions of alkenes or
 3,4-dihydro-(2H)-pyran with urea/thiourea-aldehyde mixtures: [4 + 2]
 cycloaddition vs Biginelli-type reaction.
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_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2599
_journal_page_last               2602
_journal_paper_doi               10.1021/ol060874b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C17 H19 Cl N2 S'
_chemical_formula_weight         318.85
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                 107.272(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0868(16)
_cell_length_b                   9.7252(18)
_cell_length_c                   9.8440(17)
_cell_measurement_reflns_used    31
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.66
_cell_measurement_theta_min      3.02
_cell_volume                     830.7(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\w scans'
_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  0.0088
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3611
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        5.32
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8616
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_coef       0.013(2)
_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   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                2738
_reflns_number_total             3069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060874brom20060507_042750.cif
_cod_data_source_block           y2058
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_sg_symbol_H-M      Pn
_cod_database_code               1506026