#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009082.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_2009082
loop_
_publ_author_name
'Lalancette, R. A.'
'Thompson, H. W.'
'Brunskill, A. P. J.'
_publ_section_title
;
 (+)-<i>cis</i>-Pinonic acid: catemeric hydrogen bonding in a
 non-racemic \e-keto acid
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1908
_journal_page_last               1911
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C10 H16 O3'
_chemical_formula_sum            'C10 H16 O3'
_chemical_formula_weight         184.23
_chemical_melting_point          341
_chemical_name_common            '(+)-cis-Pinonic Acid'
_chemical_name_systematic
;
(1S,3S)-(+)-cis-3-acetyl-2,2-dimethylcyclobutaneacetic acid
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6250(10)
_cell_length_b                   11.4760(10)
_cell_length_c                   7.1270(10)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.57
_cell_measurement_theta_min      3.48
_cell_volume                     523.32(12)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\q scans'
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2350
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        'variation <1'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(face-indexed numerical; Sheldrick, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.12
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.089
_reflns_number_gt                966
_reflns_number_total             1090
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bk1455.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P2~1~
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '341K' was changed to '341' - the
value should be numeric and without a unit
designator.

'_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               2009082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.9258(3) 0.30659(15) 0.4528(3) 0.0707(6) Uani d . 1 O
O2 0.4676(3) 0.78521(17) 0.0241(3) 0.0664(6) Uani d . 1 O
O3 0.1817(3) 0.68570(19) -0.1143(3) 0.0642(6) Uani d . 1 O
H3 0.172(6) 0.732(4) -0.191(5) 0.083(12) Uiso d . 1 H
C1 0.6010(3) 0.60859(19) 0.3181(3) 0.0404(5) Uani d . 1 C
C2 0.6333(3) 0.5405(2) 0.5117(3) 0.0439(5) Uani d . 1 C
C3 0.8547(3) 0.50761(18) 0.4859(3) 0.0401(5) Uani d . 1 C
C4 0.7731(4) 0.5350(2) 0.2693(3) 0.0465(6) Uani d . 1 C
C5 0.6291(6) 0.6136(3) 0.6882(4) 0.0818(11) Uani d . 1 C
C6 0.4907(5) 0.4341(3) 0.4921(6) 0.0703(9) Uani d . 1 C
C7 0.9364(3) 0.3897(2) 0.5583(3) 0.0447(5) Uani d . 1 C
C8 1.0276(4) 0.3782(3) 0.7726(4) 0.0581(7) Uani d . 1 C
C9 0.3832(4) 0.6137(3) 0.1827(4) 0.0539(6) Uani d . 1 C
C10 0.3555(4) 0.7041(2) 0.0258(3) 0.0431(5) Uani d . 1 C
H1A 0.6528 0.6883 0.3471 0.041(6) Uiso calc R 1 H
H3A 0.9562 0.5672 0.5476 0.048(7) Uiso calc R 1 H
H4A 0.7216 0.4673 0.1896 0.058(8) Uiso calc R 1 H
H4B 0.8699 0.5794 0.2162 0.054(8) Uiso calc R 1 H
H5A 0.7270 0.6766 0.7004 0.095(7) Uiso calc R 1 H
H5B 0.6663 0.5659 0.8027 0.095(7) Uiso calc R 1 H
H5C 0.4911 0.6446 0.6732 0.095(7) Uiso calc R 1 H
H6A 0.5011 0.3889 0.3817 0.090(7) Uiso calc R 1 H
H6B 0.3488 0.4592 0.4748 0.090(7) Uiso calc R 1 H
H6C 0.5325 0.3874 0.6074 0.090(7) Uiso calc R 1 H
H8A 1.1658 0.4107 0.8072 0.077(9) Uiso calc PR 0.62(4) H
H8B 1.0342 0.2973 0.8081 0.077(9) Uiso calc PR 0.62(4) H
H8C 0.9413 0.4191 0.8402 0.077(9) Uiso calc PR 0.62(4) H
H8D 0.9284 0.3407 0.8298 0.077(9) Uiso calc PR 0.38(4) H
H8E 1.0600 0.4541 0.8289 0.077(9) Uiso calc PR 0.38(4) H
H8F 1.1529 0.3323 0.7968 0.077(9) Uiso calc PR 0.38(4) H
H9A 0.3494 0.5380 0.1223 0.072(9) Uiso calc R 1 H
H9B 0.2844 0.6294 0.2589 0.071(9) 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 0.0845(14) 0.0505(11) 0.0604(11) 0.0203(10) -0.0112(9) -0.0164(9)
O2 0.0721(13) 0.0565(11) 0.0562(11) -0.0144(10) -0.0092(9) 0.0139(9)
O3 0.0585(11) 0.0655(12) 0.0538(11) -0.0083(10) -0.0120(9) 0.0149(10)
C1 0.0439(11) 0.0345(10) 0.0388(11) -0.0023(9) 0.0036(9) 0.0041(9)
C2 0.0438(12) 0.0458(12) 0.0417(12) 0.0091(10) 0.0105(9) 0.0091(10)
C3 0.0387(11) 0.0365(11) 0.0415(11) -0.0014(9) 0.0036(8) -0.0030(9)
C4 0.0508(13) 0.0467(13) 0.0429(12) -0.0011(11) 0.0139(10) 0.0016(10)
C5 0.104(3) 0.097(2) 0.0461(14) 0.052(2) 0.0224(15) 0.0052(16)
C6 0.0492(14) 0.077(2) 0.082(2) -0.0007(13) 0.0135(13) 0.0400(17)
C7 0.0395(11) 0.0406(11) 0.0488(12) 0.0027(10) 0.0020(10) -0.0067(10)
C8 0.0616(16) 0.0526(15) 0.0523(14) 0.0106(13) 0.0007(13) 0.0029(12)
C9 0.0455(13) 0.0556(14) 0.0532(14) -0.0043(12) -0.0004(11) 0.0131(12)
C10 0.0452(12) 0.0420(12) 0.0385(11) 0.0008(11) 0.0040(9) 0.0002(9)
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
C9 C1 C4 121.3(2) ?
C9 C1 C2 118.39(19) ?
C4 C1 C2 89.15(17) ?
C5 C2 C6 111.9(3) ?
C5 C2 C1 115.5(2) ?
C6 C2 C1 112.4(2) ?
C5 C2 C3 116.6(2) ?
C6 C2 C3 111.8(2) ?
C1 C2 C3 86.24(16) ?
C7 C3 C4 122.31(19) ?
C7 C3 C2 116.19(19) ?
C4 C3 C2 88.43(16) ?
C3 C4 C1 88.47(16) ?
O1 C7 C8 120.6(2) ?
O1 C7 C3 122.8(2) ?
C8 C7 C3 116.5(2) ?
C10 C9 C1 114.4(2) ?
O2 C10 O3 122.4(2) ?
O2 C10 C9 126.2(2) y
O3 C10 C9 111.3(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.206(3) y
O2 C10 1.192(3) y
O3 C10 1.331(3) y
C1 C9 1.515(3) ?
C1 C4 1.530(3) ?
C1 C2 1.552(3) ?
C2 C5 1.518(4) ?
C2 C6 1.528(4) ?
C2 C3 1.571(3) ?
C3 C7 1.498(3) ?
C3 C4 1.530(3) ?
C7 C8 1.496(3) ?
C9 C10 1.501(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
C9 C1 C2 C5 -96.0(3)
C4 C1 C2 C5 138.4(2)
C9 C1 C2 C6 34.2(3)
C4 C1 C2 C6 -91.4(2)
C9 C1 C2 C3 146.2(2)
C4 C1 C2 C3 20.60(16)
C5 C2 C3 C7 97.0(3)
C6 C2 C3 C7 -33.6(3)
C1 C2 C3 C7 -146.22(19)
C5 C2 C3 C4 -137.4(2)
C6 C2 C3 C4 92.0(2)
C1 C2 C3 C4 -20.60(16)
C7 C3 C4 C1 141.2(2)
C2 C3 C4 C1 20.87(16)
C9 C1 C4 C3 -144.3(2)
C2 C1 C4 C3 -21.14(16)
C4 C3 C7 O1 -6.8(4)
C2 C3 C7 O1 99.1(3)
C4 C3 C7 C8 175.0(2)
C2 C3 C7 C8 -79.0(3)
C4 C1 C9 C10 -86.4(3)
C2 C1 C9 C10 165.6(2)
C1 C9 C10 O2 -17.6(4)
C1 C9 C10 O3 164.5(2)