#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009115.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009115
loop_
_publ_author_name
'Brunskill, A. P. J.'
'Lalancette, R. A.'
'Thompson, H. W.'
_publ_section_title
;
 (+-)-3-Benzoylbicyclo[2.2.1]heptane-2-carboxylic acid: structures and
 hydrogen-bonding patterns of the di-<i>endo</i> and the
 2-<i>endo</i>-3-<i>exo</i> isomers
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1905
_journal_page_last               1908
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28
_chemical_melting_point          451
_chemical_name_systematic
;
(+-)-endo3-Benzoylbicyclo[2.2.1]heptane-endo2-carboxylic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.866(2)
_cell_length_b                   6.010(3)
_cell_length_c                   21.697(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.83
_cell_measurement_theta_min      3.07
_cell_volume                     1268.6(7)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2\q/\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3188
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        'No decay. Variation < 1'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tablet
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    'For hydrogen treatment see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.4905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                1315
_reflns_number_total             2232
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fg1565.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21/c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2954(2) 0.5079(3) 0.85762(9) 0.0598(6) Uani d . 1 O
O2 0.3405(2) 0.4078(4) 1.00062(9) 0.0641(6) Uani d . 1 O
O3 0.4966(2) 0.2743(4) 0.94631(9) 0.0661(7) Uani d . 1 O
H3 0.550(3) 0.393(6) 0.9648(15) 0.080 Uiso d . 1 H
C1 0.1346(3) 0.0838(5) 0.94577(14) 0.0530(8) Uani d . 1 C
C2 0.2777(3) 0.1079(5) 0.92746(12) 0.0467(7) Uani d . 1 C
C3 0.2468(3) 0.1202(5) 0.85414(11) 0.0451(7) Uani d . 1 C
C4 0.0892(3) 0.0716(5) 0.84119(14) 0.0564(8) Uani d . 1 C
C5 0.0093(3) 0.2761(6) 0.85661(14) 0.0639(9) Uani d . 1 C
C6 0.0475(3) 0.2906(5) 0.92868(14) 0.0613(9) Uani d . 1 C
C7 0.0724(3) -0.0832(5) 0.89547(15) 0.0639(9) Uani d . 1 C
C8 0.3721(3) 0.2821(5) 0.96061(12) 0.0513(8) Uani d . 1 C
C9 0.2831(3) 0.3377(5) 0.82634(12) 0.0433(7) Uani d . 1 C
C10 0.3035(3) 0.3467(5) 0.75936(11) 0.0409(7) Uani d . 1 C
C11 0.2716(3) 0.1720(5) 0.71790(12) 0.0526(8) Uani d . 1 C
C12 0.2948(3) 0.1896(6) 0.65650(13) 0.0641(9) Uani d . 1 C
C13 0.3508(3) 0.3799(6) 0.63697(14) 0.0622(9) Uani d . 1 C
C14 0.3831(3) 0.5567(6) 0.67777(13) 0.0585(8) Uani d . 1 C
C15 0.3593(3) 0.5395(5) 0.73857(12) 0.0494(8) Uani d . 1 C
H1A 0.1358 0.0320 0.9887 0.053(4) Uiso calc R 1 H
H2A 0.3241 -0.0349 0.9376 0.053(4) Uiso calc R 1 H
H3A 0.2954 -0.0010 0.8369 0.053(4) Uiso calc R 1 H
H4A 0.0562 0.0084 0.7998 0.053(4) Uiso calc R 1 H
H5A -0.0888 0.2557 0.8437 0.072(4) Uiso calc R 1 H
H5B 0.0382 0.4085 0.8368 0.072(4) Uiso calc R 1 H
H6A 0.0995 0.4247 0.9413 0.072(4) Uiso calc R 1 H
H6B -0.0342 0.2885 0.9482 0.072(4) Uiso calc R 1 H
H7A 0.1259 -0.2188 0.8959 0.072(4) Uiso calc R 1 H
H7B -0.0229 -0.1180 0.8971 0.072(4) Uiso calc R 1 H
H11A 0.2344 0.0418 0.7312 0.060(4) Uiso calc R 1 H
H12A 0.2722 0.0721 0.6288 0.060(4) Uiso calc R 1 H
H13A 0.3672 0.3907 0.5961 0.060(4) Uiso calc R 1 H
H14A 0.4206 0.6863 0.6643 0.060(4) Uiso calc R 1 H
H15B 0.3809 0.6584 0.7659 0.060(4) Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0881(16) 0.0432(13) 0.0520(12) -0.0132(12) 0.0230(11) -0.0107(10)
O2 0.0623(13) 0.0895(17) 0.0439(11) -0.0138(13) 0.0185(10) -0.0183(12)
O3 0.0476(13) 0.0882(19) 0.0633(13) -0.0068(13) 0.0118(10) -0.0236(13)
C1 0.0585(18) 0.0517(19) 0.0522(17) -0.0097(17) 0.0191(14) 0.0054(15)
C2 0.0508(17) 0.0424(18) 0.0472(15) 0.0020(15) 0.0091(13) 0.0057(14)
C3 0.0490(17) 0.0432(18) 0.0438(15) -0.0041(15) 0.0093(13) -0.0064(13)
C4 0.0543(18) 0.057(2) 0.0564(17) -0.0139(17) 0.0040(15) -0.0089(16)
C5 0.0432(17) 0.065(2) 0.082(2) -0.0025(17) 0.0061(16) 0.0070(19)
C6 0.0557(19) 0.055(2) 0.079(2) -0.0012(17) 0.0277(17) -0.0013(18)
C7 0.058(2) 0.0492(19) 0.088(2) -0.0121(17) 0.0246(17) 0.0003(19)
C8 0.0502(18) 0.066(2) 0.0380(15) 0.0015(17) 0.0090(13) 0.0049(16)
C9 0.0386(15) 0.0458(18) 0.0453(15) -0.0041(14) 0.0063(12) -0.0042(15)
C10 0.0389(15) 0.0445(17) 0.0379(14) 0.0010(14) 0.0023(12) -0.0019(13)
C11 0.0560(18) 0.056(2) 0.0442(15) -0.0064(16) 0.0042(13) -0.0017(15)
C12 0.074(2) 0.073(2) 0.0451(17) -0.007(2) 0.0080(15) -0.0130(18)
C13 0.0571(19) 0.091(3) 0.0396(15) 0.000(2) 0.0112(14) -0.0016(19)
C14 0.0569(19) 0.067(2) 0.0531(18) -0.0066(18) 0.0147(15) 0.0089(18)
C15 0.0509(18) 0.0521(19) 0.0456(15) -0.0004(16) 0.0089(14) -0.0036(15)
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_publ_flag
C8 O3 H3 110(2) ?
C6 C1 C7 102.6(3) ?
C6 C1 C2 111.5(2) ?
C7 C1 C2 98.8(2) ?
C8 C2 C1 117.7(2) ?
C8 C2 C3 116.9(2) ?
C1 C2 C3 103.5(2) ?
C9 C3 C4 112.7(2) ?
C9 C3 C2 115.3(2) ?
C4 C3 C2 101.1(2) ?
C5 C4 C7 101.2(2) ?
C5 C4 C3 110.2(2) ?
C7 C4 C3 102.0(2) ?
C4 C5 C6 102.6(2) ?
C1 C6 C5 103.5(2) ?
C4 C7 C1 93.9(2) ?
O2 C8 O3 123.0(3) ?
O2 C8 C2 123.8(3) y
O3 C8 C2 113.0(3) y
O1 C9 C10 119.4(3) ?
O1 C9 C3 120.8(2) ?
C10 C9 C3 119.9(2) ?
C11 C10 C15 118.7(2) ?
C11 C10 C9 123.3(3) ?
C15 C10 C9 117.9(2) ?
C10 C11 C12 120.5(3) ?
C13 C12 C11 119.9(3) ?
C12 C13 C14 120.3(3) ?
C15 C14 C13 119.7(3) ?
C14 C15 C10 120.8(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.223(3) y
O2 C8 1.229(3) y
O3 C8 1.317(3) y
O3 H3 0.93(3) y
C1 C6 1.521(4) ?
C1 C7 1.534(4) ?
C1 C2 1.537(4) ?
C2 C8 1.502(4) ?
C2 C3 1.571(3) ?
C3 C9 1.507(4) ?
C3 C4 1.561(4) ?
C4 C5 1.527(4) ?
C4 C7 1.531(4) ?
C5 C6 1.549(4) ?
C9 C10 1.501(4) ?
C10 C11 1.384(4) ?
C10 C15 1.390(4) ?
C11 C12 1.393(4) ?
C12 C13 1.368(4) ?
C13 C14 1.386(4) ?
C14 C15 1.382(4) ?
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 C8 65.4(3)
C7 C1 C2 C8 172.8(2)
C6 C1 C2 C3 -65.3(3)
C7 C1 C2 C3 42.1(3)
C8 C2 C3 C9 -16.0(4)
C1 C2 C3 C9 115.2(3)
C8 C2 C3 C4 -137.8(3)
C1 C2 C3 C4 -6.6(3)
C9 C3 C4 C5 -48.1(3)
C2 C3 C4 C5 75.5(3)
C9 C3 C4 C7 -155.0(2)
C2 C3 C4 C7 -31.3(3)
C7 C4 C5 C6 38.8(3)
C3 C4 C5 C6 -68.5(3)
C7 C1 C6 C5 -31.7(3)
C2 C1 C6 C5 73.2(3)
C4 C5 C6 C1 -4.3(3)
C5 C4 C7 C1 -56.8(3)
C3 C4 C7 C1 56.9(3)
C6 C1 C7 C4 54.2(3)
C2 C1 C7 C4 -60.3(3)
C1 C2 C8 O2 -1.2(4)
C3 C2 C8 O2 123.1(3)
C1 C2 C8 O3 173.5(3)
C3 C2 C8 O3 -62.3(3)
C4 C3 C9 O1 94.5(3)
C2 C3 C9 O1 -20.9(4)
C4 C3 C9 C10 -85.0(3)
C2 C3 C9 C10 159.6(2)
O1 C9 C10 C11 -169.9(3)
C3 C9 C10 C11 9.7(4)
O1 C9 C10 C15 11.2(4)
C3 C9 C10 C15 -169.3(2)
C15 C10 C11 C12 -0.2(4)
C9 C10 C11 C12 -179.1(3)
C10 C11 C12 C13 0.7(5)
C11 C12 C13 C14 -0.8(5)
C12 C13 C14 C15 0.4(5)
C13 C14 C15 C10 0.1(4)
C11 C10 C15 C14 -0.2(4)
C9 C10 C15 C14 178.8(3)