Intermolecular tandem addition-cyclization of bromoallenes: a facile synthesis of methylenecyclopropyl carboxylates and polysubstituted furans.
Xu, Lubin; Huang, Xian; Zhong, Fangrui; Organic letters 8 (2006) 5061–5064; doi:10.1021/ol061993u

data_1506239
_publ_section_title
;
 Intermolecular tandem addition-cyclization of bromoallenes: a facile
 synthesis of methylenecyclopropyl carboxylates and polysubstituted
 furans.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5061
_journal_page_last               5064
_journal_paper_doi               10.1021/ol061993u
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C14 H13 Br O4'
_chemical_formula_weight         325.15
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.526(3)
_cell_angle_beta                 78.836(3)
_cell_angle_gamma                62.414(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9280(13)
_cell_length_b                   7.9969(13)
_cell_length_c                   12.261(2)
_cell_measurement_reflns_used    1755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.690
_cell_measurement_theta_min      5.750
_cell_volume                     675.69(19)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.1195
_diffrn_reflns_av_sigmaI/netI    0.0982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3979
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    3.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75897
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.289
_refine_diff_density_max         1.226
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.059(7)
_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   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                2085
_reflns_number_total             2867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061993usi20060810_104046.cif
_cod_data_source_block           cd2673
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        675.72(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506239