Sequential organocatalytic Stetter and Michael-Aldol condensation reaction: asymmetric synthesis of fully substituted cyclopentenes via a [1 + 2 + 2] annulation strategy.
Hong, Bor-Cherng; Dange, Nitin S.; Hsu, Che-Sheng; Liao, Ju-Hsiou; Organic letters 12 (2010) 4812–4815; doi:10.1021/ol101969t

data_1503243
_publ_section_title
;
 Sequential organocatalytic Stetter and Michael-Aldol condensation
 reaction: asymmetric synthesis of fully substituted cyclopentenes via a
 [1 + 2 + 2] annulation strategy.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4812
_journal_page_last               4815
_journal_paper_doi               10.1021/ol101969t
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H22 Br N O4'
_chemical_formula_weight         444.31
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 113.700(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5060(14)
_cell_length_b                   12.0613(12)
_cell_length_c                   25.6865(18)
_cell_measurement_reflns_used    938
_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      -23.529
_cell_volume                     4115.1(7)
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines(Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            47208
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_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    2.025
_exptl_absorpt_correction_T_max  0.9126
_exptl_absorpt_correction_T_min  0.8110
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.1833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                6670
_reflns_number_total             9973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101969t_si_001.cif
_cod_data_source_block           nsd04
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4115.1(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C22 H22 Br1 N1 O4'
_cod_database_code               1503243