Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers of spirotryprostatin A.
Cheng, Mou-Nuo; Wang, Hao; Gong, Liu-Zhu; Organic letters 13 (2011) 2418–2421; doi:10.1021/ol200652j

data_1502146
_publ_section_title
;
 Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide
 to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers
 of spirotryprostatin A.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2418
_journal_page_last               2421
_journal_paper_doi               10.1021/ol200652j
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 Br N2 O8'
_chemical_formula_weight         549.37
_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                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.066(5)
_cell_length_b                   8.898(5)
_cell_length_c                   34.816(5)
_cell_measurement_reflns_used    11328
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2078
_cell_measurement_theta_min      2.7778
_cell_volume                     2499(2)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0766
_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       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            37003
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.6046
_exptl_absorpt_correction_T_min  0.5362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
 (compiled Feb 27 2009,15:38:38)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         6007
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0626P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                3280
_reflns_number_total             6007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200652j_si_001.cif
_cod_data_source_block           090407-MO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               1502146