#------------------------------------------------------------------------------
#$Date: 2019-11-25 06:55:24 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/96/4129605.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_4129605
loop_
_publ_author_name
'Hatano, Manabu'
'Goto, Yuta'
'Izumiseki, Atsuto'
'Akakura, Matsujiro'
'Ishihara, Kazuaki'
_publ_section_title
;
 Boron Tribromide-Assisted Chiral Phosphoric Acid Catalyst for a Highly
 Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13472
_journal_page_last               13475
_journal_paper_doi               10.1021/jacs.5b08693
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration (3S,3aS,5R,6R,6aR)
_chemical_formula_sum            'C9 H8 Br F3 O2'
_chemical_formula_weight         285.06
_chemical_name_common
;
(3S,3aS,5R,6R,6aR)-6-Bromo-3-(trifluoromethyl)hexahydro
-2H-3,5-methanocyclopenta[b]furan-2-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.365(2)
_cell_length_b                   12.061(4)
_cell_length_c                   12.520(4)
_cell_measurement_temperature    93(2)
_cell_volume                     961.1(5)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8227
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.254
_exptl_absorpt_coefficient_mu    4.298
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0089P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0360
_refine_ls_wR_factor_ref         0.0362
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                1962
_reflns_number_total             2163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b08693_si_002.cif
_cod_data_source_block           CrystalClear
_cod_database_code               4129605
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.480
_shelx_estimated_absorpt_t_max   0.673
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
Br1 Br 0.26639(4) 0.14991(2) -0.01938(2) 0.02361(8) Uani 1 1 d
F1 F -0.2049(2) -0.15821(13) 0.30933(11) 0.0251(4) Uani 1 1 d
F2 F -0.2826(3) -0.27874(12) 0.18889(12) 0.0256(4) Uani 1 1 d
F3 F -0.5107(2) -0.15602(15) 0.23595(14) 0.0316(4) Uani 1 1 d
C6 C 0.0034(4) 0.0738(2) 0.0197(2) 0.0168(5) Uani 1 1 d
H6 H -0.100(4) 0.106(2) -0.025(2) 0.010(6) Uiso 1 1 d
O2 O -0.1626(3) -0.09327(15) -0.05171(15) 0.0205(4) Uani 1 1 d
O1 O -0.4799(3) -0.15483(15) -0.00125(15) 0.0260(4) Uani 1 1 d
C8 C -0.2578(5) 0.0314(2) 0.1589(2) 0.0172(5) Uani 1 1 d
H8 H -0.289(4) 0.041(2) 0.231(2) 0.016(7) Uiso 1 1 d
C3 C -0.3059(4) -0.1715(2) 0.2159(2) 0.0202(6) Uani 1 1 d
C1 C -0.3093(4) -0.12018(19) 0.0222(2) 0.0186(6) Uani 1 1 d
C9 C 0.1060(4) -0.0049(2) 0.1852(2) 0.0177(6) Uani 1 1 d
H9 H 0.265(5) 0.007(2) 0.1711(19) 0.018(7) Uiso 1 1 d
C5 C 0.0255(4) -0.0523(2) 0.0022(2) 0.0173(6) Uani 1 1 d
H5 H 0.136(4) -0.074(2) -0.041(2) 0.014(7) Uiso 1 1 d
C7 C -0.0405(4) 0.0837(2) 0.1388(2) 0.0170(6) Uani 1 1 d
C4 C 0.0203(4) -0.0988(2) 0.1167(2) 0.0155(6) Uani 1 1 d
C2 C -0.2214(4) -0.0944(2) 0.13233(19) 0.0141(5) Uani 1 1 d
H2 H -0.034(4) 0.156(2) 0.167(2) 0.022(7) Uiso 1 1 d
H2A H 0.077(4) -0.170(3) 0.127(2) 0.021(8) Uiso 1 1 d
H2B H -0.365(4) 0.063(2) 0.123(2) 0.005(6) Uiso 1 1 d
H2C H 0.091(4) -0.017(2) 0.258(2) 0.014(7) Uiso 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'
F F 0.0171 0.0103 '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
C7 C6 C5 103.5(2)
C7 C6 Br1 111.23(18)
C5 C6 Br1 110.29(17)
C7 C6 H6 114.4(15)
C5 C6 H6 112.9(15)
Br1 C6 H6 104.7(14)
C1 O2 C5 109.31(19)
C7 C8 C2 103.2(2)
C7 C8 H8 107.2(17)
C2 C8 H8 110.8(15)
C7 C8 H2B 115.3(16)
C2 C8 H2B 114.3(16)
H8 C8 H2B 106(2)
F3 C3 F2 106.7(2)
F3 C3 F1 106.6(2)
F2 C3 F1 106.3(2)
F3 C3 C2 113.2(2)
F2 C3 C2 112.4(2)
F1 C3 C2 111.2(2)
O1 C1 O2 122.7(3)
O1 C1 C2 128.8(3)
O2 C1 C2 108.5(2)
C4 C9 C7 95.0(2)
C4 C9 H9 110.8(14)
C7 C9 H9 115.7(14)
C4 C9 H2C 113.3(17)
C7 C9 H2C 114.9(17)
H9 C9 H2C 107(2)
O2 C5 C4 106.8(2)
O2 C5 C6 108.9(2)
C4 C5 C6 103.0(2)
O2 C5 H5 105.0(15)
C4 C5 H5 117.6(16)
C6 C5 H5 115.1(16)
C6 C7 C9 101.8(2)
C6 C7 C8 107.0(2)
C9 C7 C8 101.4(2)
C6 C7 H2 115.9(16)
C9 C7 H2 118.2(17)
C8 C7 H2 110.9(17)
C9 C4 C5 104.3(2)
C9 C4 C2 105.0(2)
C5 C4 C2 97.2(2)
C9 C4 H2A 117.5(17)
C5 C4 H2A 116.9(17)
C2 C4 H2A 113.5(17)
C3 C2 C1 112.0(2)
C3 C2 C4 115.0(2)
C1 C2 C4 104.1(2)
C3 C2 C8 113.5(2)
C1 C2 C8 109.58(19)
C4 C2 C8 101.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.971(2)
F1 C3 1.345(3)
F2 C3 1.345(3)
F3 C3 1.341(3)
C6 C7 1.523(4)
C6 C5 1.543(4)
C6 H6 0.95(2)
O2 C1 1.354(3)
O2 C5 1.460(3)
O1 C1 1.200(3)
C8 C7 1.541(4)
C8 C2 1.571(3)
C8 H8 0.93(3)
C8 H2B 0.90(2)
C3 C2 1.499(4)
C1 C2 1.520(4)
C9 C4 1.521(4)
C9 C7 1.533(4)
C9 H9 1.04(3)
C9 H2C 0.93(3)
C5 C4 1.540(4)
C5 H5 0.93(2)
C7 H2 0.94(3)
C4 C2 1.552(4)
C4 H2A 0.94(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
C5 O2 C1 O1 179.1(2)
C5 O2 C1 C2 1.3(2)
C1 O2 C5 C4 22.5(3)
C1 O2 C5 C6 -88.0(2)
C7 C6 C5 O2 106.0(2)
Br1 C6 C5 O2 -134.96(18)
C7 C6 C5 C4 -7.2(2)
Br1 C6 C5 C4 111.9(2)
C5 C6 C7 C9 39.3(2)
Br1 C6 C7 C9 -79.2(2)
C5 C6 C7 C8 -66.8(2)
Br1 C6 C7 C8 174.83(16)
C4 C9 C7 C6 -54.7(2)
C4 C9 C7 C8 55.6(2)
C2 C8 C7 C6 66.1(2)
C2 C8 C7 C9 -40.2(3)
C7 C9 C4 C5 50.4(2)
C7 C9 C4 C2 -51.3(2)
O2 C5 C4 C9 -142.3(2)
C6 C5 C4 C9 -27.7(2)
O2 C5 C4 C2 -34.8(2)
C6 C5 C4 C2 79.9(2)
F3 C3 C2 C1 -68.9(3)
F2 C3 C2 C1 52.1(3)
F1 C3 C2 C1 171.2(2)
F3 C3 C2 C4 172.5(2)
F2 C3 C2 C4 -66.5(3)
F1 C3 C2 C4 52.6(3)
F3 C3 C2 C8 55.8(3)
F2 C3 C2 C8 176.8(2)
F1 C3 C2 C8 -64.1(3)
O1 C1 C2 C3 33.3(3)
O2 C1 C2 C3 -149.0(2)
O1 C1 C2 C4 158.2(3)
O2 C1 C2 C4 -24.2(2)
O1 C1 C2 C8 -93.5(3)
O2 C1 C2 C8 84.1(2)
C9 C4 C2 C3 -95.7(3)
C5 C4 C2 C3 157.3(2)
C9 C4 C2 C1 141.4(2)
C5 C4 C2 C1 34.4(2)
C9 C4 C2 C8 27.4(2)
C5 C4 C2 C8 -79.5(2)
C7 C8 C2 C3 132.1(2)
C7 C8 C2 C1 -101.9(2)
C7 C8 C2 C4 7.9(2)
