Aluminum chloride-mediated acylation of methylenecyclobutanes. A facile synthetic protocol for the construction of substituted cyclopentenes.
Jiang, Min; Shi, Min; Organic letters 10 (2008) 2239–2242; doi:10.1021/ol8006502

data_1504684
_publ_section_title
;
 Aluminum chloride-mediated acylation of methylenecyclobutanes. A facile
 synthetic protocol for the construction of substituted cyclopentenes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2239
_journal_page_last               2242
_journal_paper_doi               10.1021/ol8006502
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C18 H14 Br2 O'
_chemical_formula_weight         406.11
_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_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                 96.603(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   11.323(2)
_cell_length_b                   31.150(6)
_cell_length_c                   13.860(3)
_cell_measurement_reflns_used    1185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.280
_cell_measurement_theta_min      5.123
_cell_volume                     4856.2(16)
_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  0.1411
_diffrn_reflns_av_sigmaI/netI    0.1950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25210
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    5.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54763
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.227
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         9025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.2725
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2762
_reflns_number_total             9025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8006502-file005.cif
_cod_data_source_block           cd27638
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504684