#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025254.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_4025254
loop_
_publ_author_name
'Arata Takahashi'
'Hikaru Yanai'
'Min Zhang'
'Takaaki Sonoda'
'Masaaki Mishima'
'Takeo Taguchi'
_publ_contact_author_address
;
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences,
1432-1 Horinouchi Hachioji, Tokyo, 192-0392, Japan
;
_publ_contact_author_email       yanai@ps.toyaku.ac.jp
_publ_contact_author_name        'Hikaru Yanai'
_publ_section_title
;
 Highly Effective Vinylogous Mukaiyama-Michael Reaction Catalyzed by Silyl
 Methide Species Generated from
 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1259
_journal_page_last               1265
_journal_paper_doi               10.1021/jo902641g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C15 H21 Br O3'
_chemical_formula_sum            'C15 H21 Br O3'
_chemical_formula_weight         329.23
_chemical_name_systematic
; 
(S*)-3-bromo-5-((R*)-1-cyclohexyl-3-oxobutyl)-5-methyl-5H-furan-2-one
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '01 April 2009'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.354(6)
_cell_length_b                   10.517(3)
_cell_length_c                   7.131(2)
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.18
_cell_volume                     1526.5(8)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16690
_diffrn_reflns_theta_full        27.81
_diffrn_reflns_theta_max         27.81
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    2.695
_exptl_absorpt_correction_T_max  0.8770
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.364(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0259
_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/[σ²(Fo²)+(0.0382P)²+0.2087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                3298
_reflns_number_total             3579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902641g_si_007.cif
_cod_data_source_block           anti-3if
_cod_original_cell_volume        1526.3(8)
_cod_original_sg_symbol_Hall     'P 2c -2ac '
_cod_original_sg_symbol_H-M      'P c a 21 '
_cod_database_code               4025254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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 0.159070(10) 1.319182(17) 0.49523(5) 0.02571(7) Uani 1 1 d . . .
C1 C 0.16175(10) 1.1451(2) 0.5396(3) 0.0171(5) Uani 1 1 d . . .
C2 C 0.11555(9) 1.05837(18) 0.5136(3) 0.0156(4) Uani 1 1 d . . .
H2 H 0.0728 1.0750 0.4659 0.019 Uiso 1 1 calc R . .
C3 C 0.14081(10) 0.9293(2) 0.5709(3) 0.0152(4) Uani 1 1 d . . .
C4 C 0.09964(10) 0.87579(18) 0.7371(3) 0.0150(4) Uani 1 1 d . . .
H4 H 0.0530 0.8748 0.6926 0.018 Uiso 1 1 calc R . .
C5 C 0.11588(11) 0.73739(19) 0.7919(3) 0.0184(4) Uani 1 1 d . . .
H5 H 0.1146 0.6863 0.6736 0.022 Uiso 1 1 calc R . .
C6 C 0.18444(11) 0.7193(2) 0.8761(3) 0.0214(4) Uani 1 1 d . . .
H6A H 0.2179 0.7477 0.7844 0.026 Uiso 1 1 calc R . .
H6B H 0.1887 0.7729 0.9896 0.026 Uiso 1 1 calc R . .
C7 C 0.19730(13) 0.5804(2) 0.9282(3) 0.0286(5) Uani 1 1 d . . .
H7A H 0.1987 0.5285 0.8124 0.034 Uiso 1 1 calc R . .
H7B H 0.2407 0.5737 0.9903 0.034 Uiso 1 1 calc R . .
C8 C 0.14482(15) 0.5281(2) 1.0578(4) 0.0335(6) Uani 1 1 d . . .
H8A H 0.1463 0.5739 1.1790 0.040 Uiso 1 1 calc R . .
H8B H 0.1534 0.4370 1.0824 0.040 Uiso 1 1 calc R . .
C9 C 0.22193(10) 1.0832(2) 0.6108(3) 0.0181(4) Uani 1 1 d . . .
C10 C 0.14623(10) 0.8405(2) 0.4042(3) 0.0189(4) Uani 1 1 d . . .
H10A H 0.1696 0.8835 0.3022 0.028 Uiso 1 1 calc R . .
H10B H 0.1021 0.8167 0.3617 0.028 Uiso 1 1 calc R . .
H10C H 0.1704 0.7639 0.4409 0.028 Uiso 1 1 calc R . .
C11 C 0.10127(10) 0.96805(19) 0.9043(3) 0.0160(4) Uani 1 1 d . . .
H11A H 0.0902 0.9203 1.0197 0.019 Uiso 1 1 calc R . .
H11B H 0.1466 1.0007 0.9187 0.019 Uiso 1 1 calc R . .
C12 C 0.05504(10) 1.07957(19) 0.8870(3) 0.0167(4) Uani 1 1 d . . .
C13 C 0.07345(10) 1.19645(17) 0.9951(5) 0.0238(4) Uani 1 1 d . . .
H13A H 0.1125 1.2353 0.9386 0.036 Uiso 1 1 calc R . .
H13B H 0.0830 1.1733 1.1254 0.036 Uiso 1 1 calc R . .
H13C H 0.0369 1.2572 0.9920 0.036 Uiso 1 1 calc R . .
C14 C 0.07695(13) 0.5433(2) 0.9703(4) 0.0312(5) Uani 1 1 d . . .
H14A H 0.0432 0.5122 1.0592 0.037 Uiso 1 1 calc R . .
H14B H 0.0743 0.4910 0.8551 0.037 Uiso 1 1 calc R . .
C15 C 0.06279(12) 0.68262(19) 0.9212(4) 0.0244(5) Uani 1 1 d . . .
H15A H 0.0195 0.6887 0.8585 0.029 Uiso 1 1 calc R . .
H15B H 0.0608 0.7334 1.0379 0.029 Uiso 1 1 calc R . .
O1 O 0.27490(7) 1.12748(15) 0.6451(2) 0.0245(3) Uani 1 1 d . . .
O2 O 0.20821(7) 0.95811(13) 0.6333(2) 0.0177(3) Uani 1 1 d . . .
O3 O 0.00482(7) 1.07424(15) 0.7951(2) 0.0212(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
C2 C1 C9 109.51(19) . . ?
C2 C1 Br1 129.35(16) . . ?
C9 C1 Br1 121.13(15) . . ?
C1 C2 C3 109.87(18) . . ?
C1 C2 H2 125.1 . . ?
C3 C2 H2 125.1 . . ?
O2 C3 C2 102.37(15) . . ?
O2 C3 C10 107.21(16) . . ?
C2 C3 C10 111.51(17) . . ?
O2 C3 C4 110.23(15) . . ?
C2 C3 C4 110.37(17) . . ?
C10 C3 C4 114.42(17) . . ?
C11 C4 C5 113.23(16) . . ?
C11 C4 C3 110.52(16) . . ?
C5 C4 C3 114.73(17) . . ?
C11 C4 H4 105.9 . . ?
C5 C4 H4 105.9 . . ?
C3 C4 H4 105.9 . . ?
C6 C5 C15 111.09(18) . . ?
C6 C5 C4 114.31(17) . . ?
C15 C5 C4 110.83(17) . . ?
C6 C5 H5 106.7 . . ?
C15 C5 H5 106.7 . . ?
C4 C5 H5 106.7 . . ?
C7 C6 C5 111.69(19) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 111.9(2) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C14 110.5(2) . . ?
C7 C8 H8A 109.5 . . ?
C14 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C14 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 O2 122.6(2) . . ?
O1 C9 C1 130.1(2) . . ?
O2 C9 C1 107.32(17) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 114.44(17) . . ?
C12 C11 H11A 108.6 . . ?
C4 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C4 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O3 C12 C13 121.70(19) . . ?
O3 C12 C11 122.19(19) . . ?
C13 C12 C11 116.09(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 C15 111.34(19) . . ?
C8 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C8 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C5 C15 C14 111.3(2) . . ?
C5 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C5 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C9 O2 C3 110.86(15) . . ?
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 C1 1.859(2) . ?
C1 C2 1.323(3) . ?
C1 C9 1.477(3) . ?
C2 C3 1.508(3) . ?
C2 H2 0.9500 . ?
C3 O2 1.474(2) . ?
C3 C10 1.516(3) . ?
C3 C4 1.556(3) . ?
C4 C11 1.538(3) . ?
C4 C5 1.543(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.531(3) . ?
C5 C15 1.533(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.200(2) . ?
C9 O2 1.354(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.215(3) . ?
C12 C13 1.498(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.534(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091422
