#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:54:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180160 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105668.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7105668
loop_
_publ_author_name
HikaruYanai
'Arata Takahashi'
'Takeo Taguchi'
_publ_section_title
;
 1,4-Addition of silicon dienoates to Î+-,Î²-unsaturated aldehydes
 catalyzed by in situ-generated silicon Lewis acid
;
_journal_name_full               Chem.Commun.
_journal_page_first              8728
_journal_paper_doi               10.1039/c0cc02438d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C12 H17 Br O4'
_chemical_formula_sum            'C12 H17 Br O4'
_chemical_formula_weight         305.17
_chemical_melting_point          358.8(4)
_chemical_name_common
;(R*)-5-((S*)-1-(1,3-Dioxolan-2-yl)-3-methylbutan-2-yl)-3-
bromofuran-2(5H)-one
;
_chemical_name_systematic
;
(R*)-5-((S*)-1-(1,3-Dioxolan-2-yl)-3-methylbutan-2-yl)-3-bromofuran-2(5H)-one
;
_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_date             '17 November 09'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.254(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8580(19)
_cell_length_b                   15.388(3)
_cell_length_c                   9.3551(18)
_cell_measurement_reflns_used    3547
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.30
_cell_volume                     1272.7(4)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7094
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    3.230
_exptl_absorpt_correction_T_max  0.7057
_exptl_absorpt_correction_T_min  0.4332
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                2505
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC02438D.TXT
_cod_data_source_block           anti-5d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '85.2-86.0 C' was changed to
'358.8(4)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7105668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.68638(2) -0.077010(12) 1.10976(2) 0.02513(8) Uani 1 1 d . . .
C1 C 0.76685(19) 0.03679(11) 0.7531(2) 0.0145(3) Uani 1 1 d . . .
H1 H 0.8251 0.0061 0.7037 0.017 Uiso 1 1 calc R . .
C2 C 0.8583(2) 0.05034(12) 1.0264(2) 0.0173(4) Uani 1 1 d . . .
C3 C 0.6921(2) -0.02869(11) 0.8131(2) 0.0164(4) Uani 1 1 d . . .
H3 H 0.6203 -0.0708 0.7495 0.020 Uiso 1 1 calc R . .
C4 C 0.58549(19) 0.16186(11) 0.7132(2) 0.0151(3) Uani 1 1 d . . .
H4A H 0.5768 0.1299 0.8006 0.018 Uiso 1 1 calc R . .
H4B H 0.6539 0.2119 0.7608 0.018 Uiso 1 1 calc R . .
C5 C 0.7223(2) 0.15159(11) 0.5353(2) 0.0177(4) Uani 1 1 d . . .
H5 H 0.6433 0.1938 0.4663 0.021 Uiso 1 1 calc R . .
C6 C 0.7551(2) 0.09139(13) 0.4238(2) 0.0241(4) Uani 1 1 d . . .
H6A H 0.7809 0.1263 0.3518 0.036 Uiso 1 1 calc R . .
H6B H 0.6652 0.0562 0.3612 0.036 Uiso 1 1 calc R . .
H6C H 0.8400 0.0531 0.4871 0.036 Uiso 1 1 calc R . .
C7 C 0.2121(2) 0.24481(13) 0.5967(2) 0.0216(4) Uani 1 1 d . . .
H7A H 0.1711 0.2971 0.5296 0.026 Uiso 1 1 calc R . .
H7B H 0.1657 0.2398 0.6710 0.026 Uiso 1 1 calc R . .
C8 C 0.7419(2) -0.01869(11) 0.9687(2) 0.0171(4) Uani 1 1 d . . .
C9 C 0.6557(2) 0.10143(11) 0.6325(2) 0.0136(3) Uani 1 1 d . . .
H9 H 0.5705 0.0658 0.5539 0.016 Uiso 1 1 calc R . .
C10 C 0.1812(2) 0.16312(12) 0.4932(2) 0.0212(4) Uani 1 1 d . . .
H10A H 0.1135 0.1227 0.5135 0.025 Uiso 1 1 calc R . .
H10B H 0.1342 0.1784 0.3786 0.025 Uiso 1 1 calc R . .
C11 C 0.43146(19) 0.19529(11) 0.5993(2) 0.0145(3) Uani 1 1 d . . .
H11 H 0.4369 0.2277 0.5093 0.017 Uiso 1 1 calc R . .
C12 C 0.8639(2) 0.20452(13) 0.6371(3) 0.0264(4) Uani 1 1 d . . .
H12A H 0.9469 0.1650 0.7002 0.040 Uiso 1 1 calc R . .
H12B H 0.8427 0.2427 0.7086 0.040 Uiso 1 1 calc R . .
H12C H 0.8927 0.2397 0.5676 0.040 Uiso 1 1 calc R . .
O1 O 0.93333(16) 0.07685(8) 1.15990(16) 0.0233(3) Uani 1 1 d . . .
O2 O 0.87201(15) 0.08226(8) 0.89755(15) 0.0165(3) Uani 1 1 d . . .
O3 O 0.32802(14) 0.12519(8) 0.54078(16) 0.0216(3) Uani 1 1 d . . .
O4 O 0.37360(14) 0.24953(8) 0.68256(15) 0.0187(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C3 103.89(13) . . ?
O2 C1 C9 110.54(13) . . ?
C3 C1 C9 113.64(15) . . ?
O2 C1 H1 109.5 . . ?
C3 C1 H1 109.5 . . ?
C9 C1 H1 109.5 . . ?
O1 C2 O2 122.56(18) . . ?
O1 C2 C8 129.93(18) . . ?
O2 C2 C8 107.50(14) . . ?
C8 C3 C1 109.27(16) . . ?
C8 C3 H3 125.4 . . ?
C1 C3 H3 125.4 . . ?
C11 C4 C9 112.95(14) . . ?
C11 C4 H4A 109.0 . . ?
C9 C4 H4A 109.0 . . ?
C11 C4 H4B 109.0 . . ?
C9 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C12 C5 C6 109.67(15) . . ?
C12 C5 C9 114.07(15) . . ?
C6 C5 C9 111.81(15) . . ?
C12 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
C9 C5 H5 107.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 C10 104.88(14) . . ?
O4 C7 H7A 110.8 . . ?
C10 C7 H7A 110.8 . . ?
O4 C7 H7B 110.8 . . ?
C10 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C3 C8 C2 109.58(16) . . ?
C3 C8 Br1 129.77(15) . . ?
C2 C8 Br1 120.66(13) . . ?
C1 C9 C4 111.08(14) . . ?
C1 C9 C5 113.85(15) . . ?
C4 C9 C5 112.77(14) . . ?
C1 C9 H9 106.2 . . ?
C4 C9 H9 106.2 . . ?
C5 C9 H9 106.2 . . ?
O3 C10 C7 104.23(14) . . ?
O3 C10 H10A 110.9 . . ?
C7 C10 H10A 110.9 . . ?
O3 C10 H10B 110.9 . . ?
C7 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
O3 C11 O4 105.30(13) . . ?
O3 C11 C4 109.92(14) . . ?
O4 C11 C4 109.62(13) . . ?
O3 C11 H11 110.6 . . ?
O4 C11 H11 110.6 . . ?
C4 C11 H11 110.6 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 O2 C1 109.68(14) . . ?
C11 O3 C10 105.35(13) . . ?
C11 O4 C7 106.18(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.8667(18) . ?
C1 O2 1.467(2) . ?
C1 C3 1.496(2) . ?
C1 C9 1.539(2) . ?
C1 H1 1.0000 . ?
C2 O1 1.207(2) . ?
C2 O2 1.363(2) . ?
C2 C8 1.479(3) . ?
C3 C8 1.324(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.508(2) . ?
C4 C9 1.541(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(3) . ?
C5 C6 1.532(3) . ?
C5 C9 1.544(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 O4 1.433(2) . ?
C7 C10 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9 1.0000 . ?
C10 O3 1.437(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.417(2) . ?
C11 O4 1.422(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
