Morita-Baylis-Hillman Reaction of Masked 5-Alkylidene-2-cyclopentenones: General Entry to 5-Alkylidene-2-(hydroxyalkyl)-2-cyclopentenones
Pohmakotr, Manat; Thamapipol, Sirinporn; Tuchinda, Patoomratana; Prabpai, Samran; Kongsaeree, Palangpon; Reutrakul, Vichai; Journal of Organic Chemistry 72 (2007) 5418–5420; doi:10.1021/jo0705566

data_4023988
_publ_contact_author_address
;Department of Chemistry, Faculty of Science
Mahidol University
Rama 6 Road, Bangkok 10400, THAILAND
;
_publ_contact_author_email       scpks@mahidol.ac.th
_publ_contact_author_fax         +662-354-7151
_publ_contact_author_name        'Palangpon Kongsaeree'
_publ_contact_author_phone       +662-201-5190
_publ_section_title
;
 Morita-Baylis-Hillman Reaction of Masked 5-Alkylidene-2-cyclopentenones:
 General Entry to 5-Alkylidene-2-(hydroxyalkyl)-2-cyclopentenones
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   14
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5418
_journal_page_last               5420
_journal_paper_doi               10.1021/jo0705566
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C18 H17 N O4 '
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.337
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 122.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1375(7)
_cell_length_b                   6.3757(2)
_cell_length_c                   21.8859(10)
_cell_measurement_reflns_used    3093
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     1542.45(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.00845
_diffrn_orient_matrix_UB_12      0.04979
_diffrn_orient_matrix_UB_13      -0.05721
_diffrn_orient_matrix_UB_21      -0.13889
_diffrn_orient_matrix_UB_22      0.04354
_diffrn_orient_matrix_UB_23      0.05842
_diffrn_orient_matrix_UB_31      0.02401
_diffrn_orient_matrix_UB_32      0.04071
_diffrn_orient_matrix_UB_33      0.02674
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12125
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.019(6)
_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   1.020
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0665P)^2^+0.4764P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2254
_reflns_number_total             3111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705566si20070317_061219.cif
_cod_data_source_block           endo-3bA
_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      'P 21/c        '
_cod_original_formula_sum        'C18 H17 N O4 '
_cod_database_code               4023988