An Experimental and Theoretical Study on the Interaction of N-Heterocyclic Carbene-Derived 1,3-Dipoles with Methoxycarbonylallenes: Highly Regio- and Stereoselective [3+2]-Cycloadditions Controlled by the Structures of N-Heterocycles of 1,3-Dipoles
Ying Cheng; Bo Wang; Xiao-Rong Wang; Jian-Hong Zhang; De-Cai Fang; Journal of Organic Chemistry 74 (2009) 2357–2367; doi:10.1021/jo802687m

data_4024404
_publ_section_title
;
An Experimental and Theoretical Study on the Interaction of N-Heterocyclic
Carbene-Derived 1,3-Dipoles with Methoxycarbonylallenes: Highly Regio- and
Stereoselective [3+2]-Cycloadditions Controlled by the Structures
of N-Heterocycles of 1,3-Dipoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2357
_journal_page_last               2367
_journal_paper_doi               10.1021/jo802687m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C32 H35 N3 O2 S'
_chemical_formula_sum            'C32 H35 N3 O2 S'
_chemical_formula_weight         525.69
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6346(14)
_cell_length_b                   16.4160(17)
_cell_length_c                   11.7446(13)
_cell_measurement_reflns_used    7682
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     2821.5(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34353
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.9541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6723
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0610P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                5636
_reflns_number_total             6723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802687m_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4024404