exo-Selective construction of spiro-[butyrolactone=pyrrolidine] via 1,3]dipolar cycloaddition of azomethine ylides with alpha-methylene- -gamma-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP
Qing-Hua Li; Tang-Lin Liu; Liang Wei; Xiang Zhou; Hai-Yan Tao; Chun-Jiang Wang; Chem.Commun. 49 (2013) 9642–; doi:10.1039/c3cc45493b

data_7109876
_publ_section_title
;
 exo-Selective construction of spiro-[butyrolactone=pyrrolidine] via
 1,3]dipolar cycloaddition of azomethine ylides with alpha-methylene-
 -gamma-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP
;
_journal_name_full               Chem.Commun.
_journal_page_first              9642
_journal_paper_doi               10.1039/c3cc45493b
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C16 H16 Cl N O4'
_chemical_formula_weight         321.75
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   6.4177(9)
_cell_length_b                   12.2541(18)
_cell_length_c                   19.540(3)
_cell_measurement_reflns_used    3544
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.67
_cell_volume                     1536.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8555
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_correction_T_min  0.9197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.217
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.008(5)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0805
_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^)+(0.1668P)^2^+1.0765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.2547
_reflns_number_gt                2619
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45493b.txt
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7109876