Lewis Acid-Mediated Reactions of 1-Cyclopropyl-2-arylethanone Derivatives with Allenic Ester, Ethyl Acetoacetate, and Methyl Acrylate
Min Shi; Xiang-Ying Tang; Yong-Hua Yang; Journal of Organic Chemistry 73 (2008) 5311–5318; doi:10.1021/jo800608h

data_4023548
_publ_section_title
;
 Lewis Acid-Mediated Reactions of 1-Cyclopropyl-2-arylethanone
 Derivatives with Allenic Ester, Ethyl Acetoacetate,
 and Methyl Acrylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5311
_journal_page_last               5318
_journal_paper_doi               10.1021/jo800608h
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H14 Br O2.5'
_chemical_formula_weight         302.16
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   45.814(7)
_cell_length_b                   9.4317(13)
_cell_length_c                   11.6643(16)
_cell_measurement_reflns_used    2457
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.006
_cell_measurement_theta_min      5.625
_cell_volume                     5040.2(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7284
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    3.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71194
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.437
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.021(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0527P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                1979
_reflns_number_total             2671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800608h-File002.cif
_cod_data_source_block           cd2754
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C14 H14 Br O2.50'
_cod_database_code               4023548