#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/91/2009115.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, Andrew P. J.'
'Lalancette, Roger A.'
'Thompson, Hugh W.'
_publ_section_title
;
 (+-)-3-Benzoylbicyclo[2.2.1]heptane-2-carboxylic acid: structures and
 hydrogen-bonding patterns of the di-endo and the
 2-endo-3-exo isomers
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1905
_journal_page_last               1908
_journal_paper_doi               10.1107/S0108270199009245
_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       2θ/θ
_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/[σ²(Fo²)+(0.0264P)²+0.4905P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            fg1565.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_original_sg_symbol_H-M      'P 21/c'
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .2954(2) .5079(3) .85762(9) .0598(6) Uani d . 1 . . O
O2 .3405(2) .4078(4) 1.00062(9) .0641(6) Uani d . 1 . . O
O3 .4966(2) .2743(4) .94631(9) .0661(7) Uani d . 1 . . O
H3 .550(3) .393(6) .9648(15) .080 Uiso d . 1 . . H
C1 .1346(3) .0838(5) .94577(14) .0530(8) Uani d . 1 . . C
C2 .2777(3) .1079(5) .92746(12) .0467(7) Uani d . 1 . . C
C3 .2468(3) .1202(5) .85414(11) .0451(7) Uani d . 1 . . C
C4 .0892(3) .0716(5) .84119(14) .0564(8) Uani d . 1 . . C
C5 .0093(3) .2761(6) .85661(14) .0639(9) Uani d . 1 . . C
C6 .0475(3) .2906(5) .92868(14) .0613(9) Uani d . 1 . . C
C7 .0724(3) -.0832(5) .89547(15) .0639(9) Uani d . 1 . . C
C8 .3721(3) .2821(5) .96061(12) .0513(8) Uani d . 1 . . C
C9 .2831(3) .3377(5) .82634(12) .0433(7) Uani d . 1 . . C
C10 .3035(3) .3467(5) .75936(11) .0409(7) Uani d . 1 . . C
C11 .2716(3) .1720(5) .71790(12) .0526(8) Uani d . 1 . . C
C12 .2948(3) .1896(6) .65650(13) .0641(9) Uani d . 1 . . C
C13 .3508(3) .3799(6) .63697(14) .0622(9) Uani d . 1 . . C
C14 .3831(3) .5567(6) .67777(13) .0585(8) Uani d . 1 . . C
C15 .3593(3) .5395(5) .73857(12) .0494(8) Uani d . 1 . . C
H1A .1358 .0320 .9887 .053(4) Uiso calc R 1 . . H
H2A .3241 -.0349 .9376 .053(4) Uiso calc R 1 . . H
H3A .2954 -.0010 .8369 .053(4) Uiso calc R 1 . . H
H4A .0562 .0084 .7998 .053(4) Uiso calc R 1 . . H
H5A -.0888 .2557 .8437 .072(4) Uiso calc R 1 . . H
H5B .0382 .4085 .8368 .072(4) Uiso calc R 1 . . H
H6A .0995 .4247 .9413 .072(4) Uiso calc R 1 . . H
H6B -.0342 .2885 .9482 .072(4) Uiso calc R 1 . . H
H7A .1259 -.2188 .8959 .072(4) Uiso calc R 1 . . H
H7B -.0229 -.1180 .8971 .072(4) Uiso calc R 1 . . H
H11A .2344 .0418 .7312 .060(4) Uiso calc R 1 . . H
H12A .2722 .0721 .6288 .060(4) Uiso calc R 1 . . H
H13A .3672 .3907 .5961 .060(4) Uiso calc R 1 . . H
H14A .4206 .6863 .6643 .060(4) Uiso calc R 1 . . H
H15B .3809 .6584 .7659 .060(4) Uiso calc R 1 . . H
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_site_symmetry_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 . .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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2007204
