#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:45:11 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178822 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/76/4107620.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_4107620
loop_
_publ_author_name
'Taisuke Fujimoto'
'Kohei Endo'
'Hayato Tsuji'
'Masaharu Nakamura'
'Eiichi Nakamura'
_publ_section_title
;
 Construction of a Chiral Quaternary Carbon Center by Indium-Catalyzed
 Asymmetric α-Alkenylation of β-Ketoesters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4492
_journal_page_last               4496
_journal_paper_doi               10.1021/ja710408f
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 Br O3'
_chemical_formula_sum            'C16 H17 Br O3'
_chemical_formula_weight         337.21
_chemical_melting_point          364(1)
_chemical_name_common            TF09-126
_chemical_name_systematic
; 
(R)-ethyl 1-[1-(4-bromophenyl)vinyl]-2-oxocyclopentanecarboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   7.249(3)
_cell_length_b                   8.065(3)
_cell_length_c                   25.055(10)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      4.0673
_cell_volume                     1464.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'ORTEP III (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL-97 and Yadokari-XG (Wakita, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14353
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  0.6034
_exptl_absorpt_correction_T_min  0.3994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0211
_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)+(0.0100P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0472
_reflns_number_gt                2528
_reflns_number_total             2704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710408f-file004.cif
_cod_data_source_block           tf09-126
_cod_original_cell_volume        1464.9(10)
_cod_database_code               4107620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.5321(3) -0.0449(2) 0.09808(8) 0.0146(5) Uani 1 1 d .
C2 C 0.6804(3) -0.1552(3) 0.07015(9) 0.0186(5) Uani 1 1 d .
C3 C 0.6032(3) -0.3290(3) 0.06453(10) 0.0283(6) Uani 1 1 d .
H1 H 0.5891 -0.3586 0.0264 0.034 Uiso 1 1 calc R
H2 H 0.6862 -0.4107 0.0817 0.034 Uiso 1 1 calc R
C4 C 0.4173(3) -0.3265(3) 0.09213(9) 0.0243(6) Uani 1 1 d .
H3 H 0.4289 -0.3577 0.1302 0.029 Uiso 1 1 calc R
H4 H 0.3294 -0.4028 0.0745 0.029 Uiso 1 1 calc R
C5 C 0.3554(3) -0.1449(2) 0.08613(9) 0.0182(5) Uani 1 1 d .
H5 H 0.2565 -0.1176 0.1119 0.022 Uiso 1 1 calc R
H6 H 0.3104 -0.1226 0.0495 0.022 Uiso 1 1 calc R
O1 O 0.8271(2) -0.10740(19) 0.05482(6) 0.0250(4) Uani 1 1 d .
C6 C 0.5344(3) 0.1273(3) 0.07379(8) 0.0166(5) Uani 1 1 d .
O2 O 0.5569(2) 0.25584(16) 0.09756(5) 0.0215(3) Uani 1 1 d .
O3 O 0.50949(19) 0.11839(17) 0.02067(5) 0.0189(4) Uani 1 1 d .
C7 C 0.5176(3) 0.2774(2) -0.00805(8) 0.0175(5) Uani 1 1 d .
H7 H 0.6287 0.3406 0.0026 0.021 Uiso 1 1 calc R
H8 H 0.4070 0.3450 -0.0001 0.021 Uiso 1 1 calc R
C8 C 0.5252(3) 0.2351(2) -0.06644(8) 0.0221(5) Uani 1 1 d .
H9 H 0.6321 0.1639 -0.0733 0.033 Uiso 1 1 calc R
H10 H 0.5363 0.3372 -0.0874 0.033 Uiso 1 1 calc R
H11 H 0.4121 0.1766 -0.0767 0.033 Uiso 1 1 calc R
C9 C 0.5750(3) -0.0372(2) 0.15789(8) 0.0160(5) Uani 1 1 d .
C10 C 0.7475(3) -0.0493(2) 0.17619(9) 0.0215(5) Uani 1 1 d .
H12 H 0.7710 -0.0411 0.2134 0.026 Uiso 1 1 calc R
H13 H 0.8467 -0.0661 0.1520 0.026 Uiso 1 1 calc R
C11 C 0.4218(3) -0.0109(2) 0.19655(8) 0.0147(5) Uani 1 1 d .
C12 C 0.2811(3) 0.1032(2) 0.18738(8) 0.0157(5) Uani 1 1 d .
H14 H 0.2792 0.1638 0.1549 0.019 Uiso 1 1 calc R
C13 C 0.1438(3) 0.1297(3) 0.22494(8) 0.0180(5) Uani 1 1 d .
H15 H 0.0481 0.2075 0.2182 0.022 Uiso 1 1 calc R
C14 C 0.1476(3) 0.0420(3) 0.27214(8) 0.0178(5) Uani 1 1 d .
C15 C 0.2829(3) -0.0728(3) 0.28280(9) 0.0211(5) Uani 1 1 d .
H16 H 0.2837 -0.1324 0.3155 0.025 Uiso 1 1 calc R
C16 C 0.4180(3) -0.0993(3) 0.24458(8) 0.0197(5) Uani 1 1 d .
H17 H 0.5107 -0.1799 0.2512 0.024 Uiso 1 1 calc R
Br1 Br -0.04403(3) 0.07896(3) 0.322846(9) 0.02765(8) 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
C6 C1 C9 110.69(16)
C6 C1 C5 114.21(17)
C9 C1 C5 112.31(18)
C6 C1 C2 109.55(18)
C9 C1 C2 108.74(17)
C5 C1 C2 100.77(16)
O1 C2 C3 126.7(2)
O1 C2 C1 125.0(2)
C3 C2 C1 108.33(18)
C4 C3 C2 105.89(19)
C3 C4 C5 103.13(18)
C4 C5 C1 103.68(17)
O2 C6 O3 123.55(18)
O2 C6 C1 126.18(18)
O3 C6 C1 110.27(16)
C6 O3 C7 115.59(15)
O3 C7 C8 106.25(15)
C10 C9 C11 119.1(2)
C10 C9 C1 121.6(2)
C11 C9 C1 119.36(18)
C12 C11 C16 117.65(19)
C12 C11 C9 122.22(19)
C16 C11 C9 120.11(19)
C13 C12 C11 121.0(2)
C14 C13 C12 119.3(2)
C15 C14 C13 121.8(2)
C15 C14 Br1 119.72(16)
C13 C14 Br1 118.49(17)
C14 C15 C16 118.3(2)
C15 C16 C11 122.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.516(3)
C1 C9 1.532(3)
C1 C5 1.543(3)
C1 C2 1.561(3)
C2 O1 1.195(3)
C2 C3 1.516(3)
C3 C4 1.515(3)
C4 C5 1.540(3)
C6 O2 1.206(2)
C6 O3 1.345(2)
O3 C7 1.471(2)
C7 C8 1.503(3)
C9 C10 1.335(3)
C9 C11 1.489(3)
C11 C12 1.393(3)
C11 C16 1.399(3)
C12 C13 1.386(3)
C13 C14 1.378(3)
C14 C15 1.375(3)
C14 Br1 1.906(2)
C15 C16 1.386(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 O1 35.8(3)
C9 C1 C2 O1 -85.3(3)
C5 C1 C2 O1 156.5(2)
C6 C1 C2 C3 -142.39(19)
C9 C1 C2 C3 96.5(2)
C5 C1 C2 C3 -21.7(2)
O1 C2 C3 C4 178.0(2)
C1 C2 C3 C4 -3.9(3)
C2 C3 C4 C5 28.2(2)
C3 C4 C5 C1 -42.6(2)
C6 C1 C5 C4 156.16(18)
C9 C1 C5 C4 -76.7(2)
C2 C1 C5 C4 38.8(2)
C9 C1 C6 O2 -3.6(3)
C5 C1 C6 O2 124.3(2)
C2 C1 C6 O2 -123.5(3)
C9 C1 C6 O3 175.66(17)
C5 C1 C6 O3 -56.4(2)
C2 C1 C6 O3 55.8(2)
O2 C6 O3 C7 2.0(3)
C1 C6 O3 C7 -177.25(16)
C6 O3 C7 C8 168.80(17)
C6 C1 C9 C10 -90.7(2)
C5 C1 C9 C10 140.4(2)
C2 C1 C9 C10 29.7(3)
C6 C1 C9 C11 87.6(2)
C5 C1 C9 C11 -41.4(2)
C2 C1 C9 C11 -152.05(17)
C10 C9 C11 C12 135.9(2)
C1 C9 C11 C12 -42.3(3)
C10 C9 C11 C16 -42.5(3)
C1 C9 C11 C16 139.2(2)
C16 C11 C12 C13 0.9(3)
C9 C11 C12 C13 -177.57(18)
C11 C12 C13 C14 0.3(3)
C12 C13 C14 C15 -0.8(3)
C12 C13 C14 Br1 -179.38(15)
C13 C14 C15 C16 0.0(3)
Br1 C14 C15 C16 178.61(16)
C14 C15 C16 C11 1.2(3)
C12 C11 C16 C15 -1.7(3)
C9 C11 C16 C15 176.81(19)
