#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025251.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_4025251
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         'C14 H19 Br O3'
_chemical_formula_sum            'C14 H19 Br O3'
_chemical_formula_weight         315.20
_chemical_name_systematic
; 
(R*)-3-bromo-5-((S*)-1-cyclohexyl-3-oxobutyl)-5H-furan-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '19 December 2008'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.736(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2821(12)
_cell_length_b                   15.603(3)
_cell_length_c                   14.722(3)
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.61
_cell_volume                     1412.9(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 '
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7760
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    2.908
_exptl_absorpt_correction_T_max  0.4471
_exptl_absorpt_correction_T_min  0.3300
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0270
_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)+(0.0416P)²+0.3576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2850
_reflns_number_total             3188
_reflns_threshold_expression     >2sigma
_cod_data_source_file            jo902641g_si_004.cif
_cod_data_source_block           anti-3ie
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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 0.86034(3) 0.894642(11) -0.291253(12) 0.02063(8) Uani 1 1 d . . .
O1 O 1.2036(2) 0.91892(9) -0.09333(9) 0.0221(3) Uani 1 1 d . . .
O3 O 0.4770(2) 0.64242(8) 0.02318(9) 0.0206(3) Uani 1 1 d . . .
O2 O 0.9431(2) 0.90158(7) -0.01049(9) 0.0159(3) Uani 1 1 d . . .
C10 C 0.8717(3) 0.85018(14) 0.28265(13) 0.0253(4) Uani 1 1 d . . .
H10A H 0.8521 0.7911 0.3040 0.030 Uiso 1 1 calc R . .
H10B H 1.0132 0.8717 0.3174 0.030 Uiso 1 1 calc R . .
C7 C 0.6900(3) 0.90683(13) 0.30350(14) 0.0244(4) Uani 1 1 d . . .
H7A H 0.6867 0.9029 0.3703 0.029 Uiso 1 1 calc R . .
H7B H 0.7191 0.9672 0.2894 0.029 Uiso 1 1 calc R . .
C14 C 0.7925(3) 0.56753(12) 0.00053(14) 0.0241(4) Uani 1 1 d . . .
H14A H 0.9056 0.5615 0.0568 0.036 Uiso 1 1 calc R . .
H14B H 0.8605 0.5726 -0.0535 0.036 Uiso 1 1 calc R . .
H14C H 0.6979 0.5170 -0.0066 0.036 Uiso 1 1 calc R . .
C6 C 0.4708(3) 0.88003(12) 0.24650(13) 0.0213(4) Uani 1 1 d . . .
H6A H 0.3579 0.9208 0.2575 0.026 Uiso 1 1 calc R . .
H6B H 0.4328 0.8225 0.2666 0.026 Uiso 1 1 calc R . .
C5 C 0.4740(3) 0.87804(12) 0.14297(13) 0.0205(4) Uani 1 1 d . . .
H5A H 0.3316 0.8575 0.1080 0.025 Uiso 1 1 calc R . .
H5B H 0.4970 0.9368 0.1216 0.025 Uiso 1 1 calc R . .
C11 C 0.8746(3) 0.84861(13) 0.17884(12) 0.0201(4) Uani 1 1 d . . .
H11A H 0.9086 0.9066 0.1584 0.024 Uiso 1 1 calc R . .
H11B H 0.9893 0.8089 0.1675 0.024 Uiso 1 1 calc R . .
C13 C 0.6597(3) 0.64646(11) 0.00807(11) 0.0171(3) Uani 1 1 d . . .
C1 C 1.0151(3) 0.90693(10) -0.09109(13) 0.0165(3) Uani 1 1 d . . .
C12 C 0.7698(3) 0.73089(10) -0.00425(12) 0.0161(3) Uani 1 1 d . . .
H12A H 0.7898 0.7351 -0.0691 0.019 Uiso 1 1 calc R . .
H12B H 0.9158 0.7314 0.0368 0.019 Uiso 1 1 calc R . .
C8 C 0.8254(3) 0.89581(10) -0.16812(12) 0.0159(3) Uani 1 1 d . . .
C9 C 0.6468(3) 0.88712(10) -0.13380(12) 0.0154(3) Uani 1 1 d . . .
H9 H 0.5037 0.8802 -0.1693 0.018 Uiso 1 1 calc R . .
C2 C 0.7071(3) 0.88996(10) -0.03035(12) 0.0143(3) Uani 1 1 d . . .
H2 H 0.6376 0.9411 -0.0076 0.017 Uiso 1 1 calc R . .
C4 C 0.6536(3) 0.81953(10) 0.12278(11) 0.0145(3) Uani 1 1 d . . .
H4 H 0.6256 0.7615 0.1466 0.017 Uiso 1 1 calc R . .
C3 C 0.6430(3) 0.80932(10) 0.01747(11) 0.0142(3) Uani 1 1 d . . .
H3 H 0.4871 0.7980 -0.0111 0.017 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 109.74(13) . . ?
C7 C10 C11 111.81(16) . . ?
C7 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C7 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C6 C7 C10 111.18(16) . . ?
C6 C7 H7A 109.4 . . ?
C10 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C10 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C6 C5 111.24(16) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C4 C5 C6 111.49(15) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C4 C11 C10 110.40(15) . . ?
C4 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C4 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O3 C13 C14 122.01(17) . . ?
O3 C13 C12 122.56(16) . . ?
C14 C13 C12 115.42(16) . . ?
O1 C1 O2 122.53(17) . . ?
O1 C1 C8 129.80(17) . . ?
O2 C1 C8 107.67(15) . . ?
C13 C12 C3 113.63(14) . . ?
C13 C12 H12A 108.8 . . ?
C3 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C3 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C9 C8 C1 109.39(16) . . ?
C9 C8 Br1 130.00(15) . . ?
C1 C8 Br1 120.61(13) . . ?
C8 C9 C2 109.05(16) . . ?
C8 C9 H9 125.5 . . ?
C2 C9 H9 125.5 . . ?
O2 C2 C9 104.12(14) . . ?
O2 C2 C3 111.06(13) . . ?
C9 C2 C3 114.07(14) . . ?
O2 C2 H2 109.1 . . ?
C9 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C5 C4 C11 110.03(14) . . ?
C5 C4 C3 111.97(14) . . ?
C11 C4 C3 114.81(13) . . ?
C5 C4 H4 106.5 . . ?
C11 C4 H4 106.5 . . ?
C3 C4 H4 106.5 . . ?
C12 C3 C2 111.34(13) . . ?
C12 C3 C4 111.98(13) . . ?
C2 C3 C4 114.44(14) . . ?
C12 C3 H3 106.1 . . ?
C2 C3 H3 106.1 . . ?
C4 C3 H3 106.1 . . ?
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 1.8700(18) . ?
O1 C1 1.206(2) . ?
O3 C13 1.215(2) . ?
O2 C1 1.356(2) . ?
O2 C2 1.463(2) . ?
C10 C7 1.523(3) . ?
C10 C11 1.532(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 C6 1.518(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 C13 1.504(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 C5 1.529(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 C4 1.532(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C12 1.516(2) . ?
C1 C8 1.479(3) . ?
C12 C3 1.529(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C8 C9 1.328(2) . ?
C9 C2 1.493(2) . ?
C9 H9 0.9500 . ?
C2 C3 1.535(2) . ?
C2 H2 1.0000 . ?
C4 C3 1.546(2) . ?
C4 H4 1.0000 . ?
C3 H3 1.0000 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45112832
