Efficient construction of highly functionalized spiro[gamma-butyrolactone-pyrrolidin-3,3'-oxindole] tricyclic skeletons via an organocatalytic 1,3-dipolar cycloaddition
Long Wang; Xiao-Mei Shi; Wei-Ping Dong; Li-Ping Zhu; Rui Wang; Chem.Commun. 49 (2013) 3458–; doi:10.1039/c3cc40669e

data_7109104
_publ_section_title
;
 Efficient construction of highly functionalized
 spiro[gamma-butyrolactone-pyrrolidin-3,3'-oxindole] tricyclic skeletons
 via an organocatalytic 1,3-dipolar cycloaddition
;
_journal_name_full               Chem.Commun.
_journal_page_first              3458
_journal_paper_doi               10.1039/c3cc40669e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 Cl N2 O5'
_chemical_formula_sum            'C23 H21 Cl N2 O5'
_chemical_formula_weight         440.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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_date             2012-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
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_cell_length_b                   16.4094(5)
_cell_length_c                   20.8853(6)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    292.19(10)
_cell_measurement_theta_max      28.5678
_cell_measurement_theta_min      3.1512
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9691
_diffrn_measurement_details
;
1 omega -20.00 25.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -19.1930 -99.0000 -30.0000 45
2 omega -48.00 29.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -57.0000 30.0000 77
3 omega 80.00 105.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -178.0000 -150.0000 25
4 omega 42.00 67.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -99.0000 -30.0000 25
5 omega -8.00 96.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 38.0000 -180.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.0248234000
_diffrn_orient_matrix_UB_13      0.0266664000
_diffrn_orient_matrix_UB_21      0.0192680000
_diffrn_orient_matrix_UB_22      0.0353826000
_diffrn_orient_matrix_UB_23      0.0186093000
_diffrn_orient_matrix_UB_31      -0.1062674000
_diffrn_orient_matrix_UB_32      0.0004150000
_diffrn_orient_matrix_UB_33      0.0098028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11081
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0714P)^2^+0.2127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                3172
_reflns_number_total             4150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40669e.txt
_cod_data_source_block           wanglong1008
_cod_original_cell_volume        2190.00(11)
_cod_database_code               7109104
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32