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#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025462.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_4025462
loop_
_publ_author_name
'Satomi Niwayama'
'Hanjoung Cho'
'Masoud Zabet-Moghaddam'
'Bruce R. Whittlesey'
_publ_section_title
;
 Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl
 Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3775
_journal_page_last               3780
_journal_paper_doi               10.1021/jo100564e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.8100(10)
_cell_angle_beta                 101.1500(10)
_cell_angle_gamma                109.2290(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9411(8)
_cell_length_b                   9.2660(11)
_cell_length_c                   10.4142(12)
_cell_measurement_temperature    293(2)
_cell_volume                     603.26(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6879
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_crystal_size_max          1.056
_exptl_crystal_size_mid          0.712
_exptl_crystal_size_min          0.434
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.000(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          1.385
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0724P)²+0.1576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                2058
_reflns_number_total             2643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100564e_si_002.cif
_cod_data_source_block           2009010901hc2brw_0m
_cod_database_code               4025462
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
O4 O 0.7794(3) -0.06399(16) 0.84289(16) 0.0797(5) Uani 1 1 d . . .
H4A H 0.8545 -0.0961 0.8925 0.120 Uiso 1 1 calc R . .
O3 O 0.9894(2) 0.16293(16) 0.97963(15) 0.0742(5) Uani 1 1 d . . .
O2 O 0.9121(2) 0.34220(16) 0.63171(14) 0.0701(4) Uani 1 1 d . . .
O1 O 0.9695(2) 0.56763(15) 0.77297(13) 0.0651(4) Uani 1 1 d . . .
C8 C 0.3138(4) 0.0863(3) 0.5821(2) 0.0887(8) Uani 1 1 d . . .
H8A H 0.4428 0.1287 0.5564 0.133 Uiso 1 1 calc R . .
H8B H 0.2027 0.1049 0.5249 0.133 Uiso 1 1 calc R . .
H8C H 0.2768 -0.0248 0.5734 0.133 Uiso 1 1 calc R . .
C9 C 0.4643(4) 0.4330(3) 0.6522(2) 0.0826(7) Uani 1 1 d . . .
H9A H 0.5416 0.5435 0.6889 0.124 Uiso 1 1 calc R . .
H9B H 0.3283 0.4168 0.5962 0.124 Uiso 1 1 calc R . .
H9C H 0.5411 0.3909 0.5995 0.124 Uiso 1 1 calc R . .
C11 C 1.0571(4) 0.6545(3) 0.6819(2) 0.0794(7) Uani 1 1 d . . .
H11A H 1.1931 0.6495 0.6822 0.119 Uiso 1 1 calc R . .
H11B H 1.0720 0.7622 0.7097 0.119 Uiso 1 1 calc R . .
H11C H 0.9648 0.6100 0.5927 0.119 Uiso 1 1 calc R . .
C6 C 0.3439(3) 0.1654(3) 0.7274(2) 0.0668(5) Uani 1 1 d . . .
H6 H 0.2044 0.1312 0.7455 0.080 Uiso 1 1 calc R . .
C7 C 0.5475(3) 0.2609(3) 0.95585(19) 0.0645(5) Uani 1 1 d . . .
H7A H 0.4249 0.2650 0.9856 0.077 Uiso 1 1 calc R . .
H7B H 0.6553 0.2610 1.0307 0.077 Uiso 1 1 calc R . .
C5 C 0.4358(3) 0.3502(3) 0.7662(2) 0.0641(5) Uani 1 1 d . . .
H5 H 0.3343 0.3817 0.8056 0.077 Uiso 1 1 calc R . .
C1 C 0.4914(3) 0.1246(2) 0.83426(19) 0.0577(5) Uani 1 1 d . . .
H1 H 0.4293 0.0201 0.8510 0.069 Uiso 1 1 calc R . .
C4 C 0.6311(3) 0.3890(2) 0.88226(18) 0.0552(4) Uani 1 1 d . . .
H4 H 0.6832 0.4962 0.9381 0.066 Uiso 1 1 calc R . .
C12 C 0.8403(3) 0.0881(2) 0.88390(17) 0.0491(4) Uani 1 1 d . . .
C10 C 0.8971(2) 0.4116(2) 0.73415(17) 0.0491(4) Uani 1 1 d . . .
C2 C 0.7096(2) 0.15910(19) 0.80152(16) 0.0469(4) Uani 1 1 d . . .
H2 H 0.6899 0.1188 0.7053 0.056 Uiso 1 1 calc R . .
C3 C 0.8055(2) 0.33977(19) 0.83808(16) 0.0461(4) Uani 1 1 d . . .
H3 H 0.9226 0.3705 0.9189 0.055 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'
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
C12 O4 H4A 109.5 . . ?
C10 O1 C11 117.08(16) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C6 C1 115.79(19) . . ?
C8 C6 C5 116.94(19) . . ?
C1 C6 C5 102.62(15) . . ?
C8 C6 H6 106.9 . . ?
C1 C6 H6 106.9 . . ?
C5 C6 H6 106.9 . . ?
C4 C7 C1 94.78(14) . . ?
C4 C7 H7A 112.8 . . ?
C1 C7 H7A 112.8 . . ?
C4 C7 H7B 112.8 . . ?
C1 C7 H7B 112.8 . . ?
H7A C7 H7B 110.2 . . ?
C9 C5 C4 117.36(17) . . ?
C9 C5 C6 116.99(19) . . ?
C4 C5 C6 102.82(15) . . ?
C9 C5 H5 106.3 . . ?
C4 C5 H5 106.3 . . ?
C6 C5 H5 106.3 . . ?
C7 C1 C6 101.67(16) . . ?
C7 C1 C2 100.88(14) . . ?
C6 C1 C2 109.45(15) . . ?
C7 C1 H1 114.4 . . ?
C6 C1 H1 114.4 . . ?
C2 C1 H1 114.4 . . ?
C7 C4 C5 100.44(15) . . ?
C7 C4 C3 99.46(14) . . ?
C5 C4 C3 113.06(14) . . ?
C7 C4 H4 114.1 . . ?
C5 C4 H4 114.1 . . ?
C3 C4 H4 114.1 . . ?
O3 C12 O4 122.01(16) . . ?
O3 C12 C2 124.06(16) . . ?
O4 C12 C2 113.93(15) . . ?
O2 C10 O1 123.48(16) . . ?
O2 C10 C3 126.29(16) . . ?
O1 C10 C3 110.18(14) . . ?
C12 C2 C3 112.57(13) . . ?
C12 C2 C1 110.93(14) . . ?
C3 C2 C1 102.26(13) . . ?
C12 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C10 C3 C2 114.74(14) . . ?
C10 C3 C4 117.73(13) . . ?
C2 C3 C4 104.26(13) . . ?
C10 C3 H3 106.4 . . ?
C2 C3 H3 106.5 . . ?
C4 C3 H3 106.4 . . ?
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
O4 C12 1.304(2) . ?
O4 H4A 0.8200 . ?
O3 C12 1.209(2) . ?
O2 C10 1.200(2) . ?
O1 C10 1.330(2) . ?
O1 C11 1.433(2) . ?
C8 C6 1.519(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C5 1.519(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C6 C1 1.540(3) . ?
C6 C5 1.572(3) . ?
C6 H6 0.9800 . ?
C7 C4 1.526(3) . ?
C7 C1 1.531(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C4 1.530(3) . ?
C5 H5 0.9800 . ?
C1 C2 1.558(2) . ?
C1 H1 0.9800 . ?
C4 C3 1.549(2) . ?
C4 H4 0.9800 . ?
C12 C2 1.502(2) . ?
C10 C3 1.492(2) . ?
C2 C3 1.537(2) . ?
C2 H2 0.9800 . ?
C3 H3 0.9800 . ?
