#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025253.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_4025253
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         'C16 H17 Br O3'
_chemical_formula_sum            'C16 H17 Br O3'
_chemical_formula_weight         337.21
_chemical_name_systematic
;
(R*)-3-bromo-5-((2S*,3S*)-5-oxo-2-phenylhexan-3-yl)-5H-furan-2-one 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '16 February 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            8
_cell_length_a                   21.609(4)
_cell_length_b                   8.9577(16)
_cell_length_c                   15.245(3)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.46
_cell_volume                     2950.9(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15617
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    2.790
_exptl_absorpt_correction_T_max  0.6638
_exptl_absorpt_correction_T_min  0.5662
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0349P)²+1.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                2843
_reflns_number_total             3397
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902641g_si_006.cif
_cod_data_source_block           anti,anti-3oe
_cod_original_cell_volume        2951.0(9)
_cod_original_sg_symbol_Hall     '-P 2n 2ab '
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               4025253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, 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 0.934717(10) 0.04386(2) 0.332918(13) 0.02403(9) Uani 1 1 d . . .
O1 O 1.04513(6) 0.12932(16) 0.47266(10) 0.0215(3) Uani 1 1 d . . .
O3 O 0.78112(6) 0.16311(15) 0.57137(10) 0.0208(3) Uani 1 1 d . . .
O2 O 0.98454(5) 0.29515(15) 0.54322(9) 0.0167(3) Uani 1 1 d . . .
C8 C 0.77147(9) 0.4899(3) 0.89321(15) 0.0262(5) Uani 1 1 d . . .
H8 H 0.7396 0.5010 0.9357 0.031 Uiso 1 1 calc R . .
C7 C 0.76859(9) 0.5681(3) 0.81466(15) 0.0247(5) Uani 1 1 d . . .
H7 H 0.7351 0.6343 0.8039 0.030 Uiso 1 1 calc R . .
C12 C 0.82102(9) 0.3955(2) 0.90937(14) 0.0242(4) Uani 1 1 d . . .
H12 H 0.8233 0.3419 0.9631 0.029 Uiso 1 1 calc R . .
C16 C 0.81983(9) -0.0691(2) 0.62404(15) 0.0214(4) Uani 1 1 d . . .
H16A H 0.7793 -0.1077 0.6060 0.032 Uiso 1 1 calc R . .
H16B H 0.8264 -0.0906 0.6864 0.032 Uiso 1 1 calc R . .
H16C H 0.8523 -0.1173 0.5893 0.032 Uiso 1 1 calc R . .
C13 C 0.93975(9) 0.5843(2) 0.66511(14) 0.0206(4) Uani 1 1 d . . .
H13A H 0.9091 0.6350 0.6284 0.031 Uiso 1 1 calc R . .
H13B H 0.9776 0.5678 0.6311 0.031 Uiso 1 1 calc R . .
H13C H 0.9492 0.6463 0.7164 0.031 Uiso 1 1 calc R . .
C6 C 0.81464(9) 0.5497(2) 0.75171(14) 0.0187(4) Uani 1 1 d . . .
H6 H 0.8119 0.6026 0.6979 0.022 Uiso 1 1 calc R . .
C11 C 0.86764(9) 0.3792(2) 0.84663(13) 0.0184(4) Uani 1 1 d . . .
H11 H 0.9018 0.3158 0.8587 0.022 Uiso 1 1 calc R . .
C1 C 0.99592(8) 0.1900(2) 0.48062(13) 0.0163(4) Uani 1 1 d . . .
C15 C 0.82193(8) 0.0961(2) 0.60948(12) 0.0153(4) Uani 1 1 d . . .
C9 C 0.93848(8) 0.1741(2) 0.42819(12) 0.0155(4) Uani 1 1 d . . .
C10 C 0.89555(8) 0.2667(2) 0.45799(12) 0.0155(4) Uani 1 1 d . . .
H10 H 0.8548 0.2767 0.4352 0.019 Uiso 1 1 calc R . .
C4 C 0.91369(8) 0.4332(2) 0.69569(13) 0.0149(4) Uani 1 1 d . . .
H4 H 0.9485 0.3744 0.7216 0.018 Uiso 1 1 calc R . .
C5 C 0.86491(8) 0.4545(2) 0.76655(13) 0.0149(4) Uani 1 1 d . . .
C14 C 0.87770(8) 0.1766(2) 0.64757(13) 0.0143(4) Uani 1 1 d . . .
H14A H 0.9155 0.1211 0.6305 0.017 Uiso 1 1 calc R . .
H14B H 0.8747 0.1732 0.7123 0.017 Uiso 1 1 calc R . .
C2 C 0.92168(8) 0.3528(2) 0.53323(13) 0.0143(4) Uani 1 1 d . . .
H2 H 0.9241 0.4605 0.5163 0.017 Uiso 1 1 calc R . .
C3 C 0.88551(7) 0.33990(19) 0.61944(12) 0.0127(3) Uani 1 1 d . . .
H3 H 0.8431 0.3803 0.6082 0.015 Uiso 1 1 calc R . .
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
C1 O2 C2 109.81(14) . . ?
C12 C8 C7 119.71(19) . . ?
C12 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C12 C11 119.9(2) . . ?
C8 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C11 C12 121.20(19) . . ?
C5 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
O1 C1 O2 122.92(18) . . ?
O1 C1 C9 130.03(19) . . ?
O2 C1 C9 107.03(15) . . ?
O3 C15 C16 122.51(17) . . ?
O3 C15 C14 121.61(17) . . ?
C16 C15 C14 115.86(16) . . ?
C10 C9 C1 109.92(17) . . ?
C10 C9 Br1 128.93(15) . . ?
C1 C9 Br1 121.10(13) . . ?
C9 C10 C2 108.79(16) . . ?
C9 C10 H10 125.6 . . ?
C2 C10 H10 125.6 . . ?
C5 C4 C13 111.01(15) . . ?
C5 C4 C3 109.07(14) . . ?
C13 C4 C3 112.92(16) . . ?
C5 C4 H4 107.9 . . ?
C13 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
C11 C5 C6 117.94(18) . . ?
C11 C5 C4 122.07(17) . . ?
C6 C5 C4 119.97(17) . . ?
C15 C14 C3 115.65(15) . . ?
C15 C14 H14A 108.4 . . ?
C3 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C3 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O2 C2 C10 104.43(14) . . ?
O2 C2 C3 110.97(14) . . ?
C10 C2 C3 115.26(15) . . ?
O2 C2 H2 108.7 . . ?
C10 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C2 C3 C14 111.56(15) . . ?
C2 C3 C4 113.60(14) . . ?
C14 C3 C4 110.27(15) . . ?
C2 C3 H3 107.0 . . ?
C14 C3 H3 107.0 . . ?
C4 C3 H3 107.0 . . ?
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 C9 1.8647(19) . ?
O1 C1 1.201(2) . ?
O3 C15 1.215(2) . ?
O2 C1 1.363(2) . ?
O2 C2 1.461(2) . ?
C8 C12 1.386(3) . ?
C8 C7 1.389(3) . ?
C8 H8 0.9500 . ?
C7 C6 1.392(3) . ?
C7 H7 0.9500 . ?
C12 C11 1.397(3) . ?
C12 H12 0.9500 . ?
C16 C15 1.497(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13 C4 1.538(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 C5 1.399(3) . ?
C6 H6 0.9500 . ?
C11 C5 1.396(3) . ?
C11 H11 0.9500 . ?
C1 C9 1.483(3) . ?
C15 C14 1.520(2) . ?
C9 C10 1.325(3) . ?
C10 C2 1.493(3) . ?
C10 H10 0.9500 . ?
C4 C5 1.521(3) . ?
C4 C3 1.556(3) . ?
C4 H4 1.0000 . ?
C14 C3 1.534(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.534(3) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45112838
