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_4024402
_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_sum            'C40 H35 N3 O2 S'
_chemical_formula_weight         621.77
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.30(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.827(4)
_cell_length_b                   14.580(3)
_cell_length_c                   26.455(5)
_cell_measurement_reflns_used    8499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      1.65
_cell_volume                     7484(3)
_computing_cell_refinement       'Rapid Auto(Rigak 2001)'
_computing_data_collection       'Rapid Auto(Rigak 2001)'
_computing_data_reduction        'Rapid Auto(Rigak 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8499
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9192
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_platon_squeeze_details
;
;
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.00140(17)
_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   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         8499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0880P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                4792
_reflns_number_total             8499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802687m_si_001.cif
_cod_data_source_block           a
_cod_depositor_comments
;
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024402