##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     no
_journal_date_recd_electronic     2007-01-16
_journal_date_accepted     2007-01-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o838
_journal_page_last     o839
_journal_paper_category     EO
_journal_coeditor_code     KP2083
_publ_contact_author_name     'Inger Søtofte'
_publ_contact_author_address
;
Department of Chemistry
DTU 207
Technical University of Denmark
Kemitorvet
DK-2800 Kgs.Lyngby
Denmark
;
_publ_contact_author_email     is@kemi.dtu.dk
_publ_contact_author_fax     '+45-45 88 31 36'
_publ_contact_author_phone     '+45-45 25 20 27'
_publ_section_title
;
rac-(1S,6S)-Methyl
6-methyl-2-oxobicyclo[4.1.0]heptane-1-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Juhl, Martin'
;
 Department of Chemistry
 DTU 207
 Technical University of Denmark
 Kemitorvet
 DK-2800 Kgs. Lyngby
 Denmark
;
    'Søtofte, Inger'
;
 Department of Chemistry
 DTU 207
 Technical University of Denmark
 Kemitorvet
 DK-2800 Kgs. Lyngby
 Denmark
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
rac-(1S,6S)-methyl 6-methyl-2-oxobicyclo[4.1.0]heptane-1-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H14 O3'
_chemical_formula_sum     'C10 H14 O3'
_chemical_formula_iupac     'C10 H14 O3'
_chemical_formula_weight     182.21
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     7.3651(6)
_cell_length_b     7.2746(6)
_cell_length_c     17.5576(14)
_cell_angle_alpha     90.00
_cell_angle_beta     92.204(2)
_cell_angle_gamma     90.00
_cell_volume     940.01(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2274
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     27.98
_cell_measurement_temperature     120(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     392
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001a)'
_exptl_absorpt_correction_T_min     0.8455
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
m.p. 321-322 K; Rf: 0.31 (Et₂O:n-pentane, 1:4); IR (film) 2928, 1732,
1693, 1437, 1354, 1243, 1216, 1111, 1077, 955, 913, 863; ¹H NMR
(500 MHz, CDCl₃) δ 3.73 (s, 3H), 2.36 (dddd, J = 0.7, 2.8, 4.8,
18.0 Hz, 1H), 2.12 (ddd, J = 6.6, 12.8, 18.0 Hz, 1H), 1.98 (ddd,
J = 3.7, 3.7, 13.8 Hz, 1H), 1.84 (ddd, J = 4.6, 13.1, 13.1 Hz, 1H),
1.76 (m, 1H), 1.59-1.51 (m, 3H), 1.19 (s, 3H); ¹³C NMR (125 MHz, CDCl₃)
δ 203.7, 169.3, 52.4, 44.5, 36.8, 29.3, 28.6,20.8, 20.4, 17.7.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12246
_diffrn_reflns_av_R_equivalents     0.0211
_diffrn_reflns_av_sigmaI/netI     0.0165
_diffrn_reflns_theta_min     2.32
_diffrn_reflns_theta_max     27.98
_diffrn_reflns_theta_full     27.98
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2274
_reflns_number_gt     2035
_reflns_threshold_expression     I>2/s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0444
_refine_ls_R_factor_gt     0.0400
_refine_ls_wR_factor_gt     0.1057
_refine_ls_wR_factor_ref     0.1094
_refine_ls_goodness_of_fit_ref     1.087
_refine_ls_restrained_S_all     1.087
_refine_ls_number_reflns     2274
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0601P)²+0.246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.385
_refine_diff_density_min     -0.177
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 2001b)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     SHELXTL
loop_
    _atom_site_type_symbol
    _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
    O O1 0.33452(13) 0.62368(12) 0.04948(5) 0.0332(2) Uani d . 1 . .
    C C1 0.29152(14) 0.52978(14) 0.10212(6) 0.0210(2) Uani d . 1 . .
    O O2 0.37054(10) 0.53980(11) 0.17224(5) 0.0259(2) Uani d . 1 . .
    C C2 0.50780(16) 0.68162(17) 0.18275(8) 0.0324(3) Uani d . 1 . .
    H H21 0.6001 0.6669 0.1445 0.049 Uiso calc R 1 . .
    H H22 0.5652 0.6709 0.2338 0.049 Uiso calc R 1 . .
    H H23 0.4508 0.8028 0.1770 0.049 Uiso calc R 1 . .
    C C3 0.14556(14) 0.38533(14) 0.09961(5) 0.0184(2) Uani d . 1 . .
    C C4 -0.01242(13) 0.42938(14) 0.14703(6) 0.0179(2) Uani d . 1 . .
    O O3 -0.04033(10) 0.58827(10) 0.16610(4) 0.0238(2) Uani d . 1 . .
    C C5 -0.13393(14) 0.27593(15) 0.17305(7) 0.0251(2) Uani d . 1 . .
    H H51 -0.2618 0.3145 0.1637 0.030 Uiso calc R 1 . .
    H H52 -0.1142 0.2615 0.2288 0.030 Uiso calc R 1 . .
    C C6 -0.10915(15) 0.08771(15) 0.13598(7) 0.0268(3) Uani d . 1 . .
    H H61 -0.1685 -0.0076 0.1667 0.032 Uiso calc R 1 . .
    H H62 -0.1685 0.0878 0.0844 0.032 Uiso calc R 1 . .
    C C7 0.09232(15) 0.04143(14) 0.13000(6) 0.0213(2) Uani d . 1 . .
    H H71 0.1477 0.0292 0.1820 0.026 Uiso calc R 1 . .
    H H72 0.1033 -0.0789 0.1043 0.026 Uiso calc R 1 . .
    C C8 0.19786(14) 0.18351(14) 0.08680(6) 0.0197(2) Uani d . 1 . .
    C C9 0.39779(16) 0.14034(16) 0.08028(7) 0.0272(3) Uani d . 1 . .
    H H91 0.4113 0.0208 0.0554 0.041 Uiso calc R 1 . .
    H H92 0.4566 0.1365 0.1313 0.041 Uiso calc R 1 . .
    H H93 0.4549 0.2358 0.0499 0.041 Uiso calc R 1 . .
    C C10 0.10513(17) 0.28945(16) 0.02340(6) 0.0272(3) Uani d . 1 . .
    H H101 -0.0230 0.2586 0.0099 0.033 Uiso calc R 1 . .
    H H102 0.1785 0.3253 -0.0203 0.033 Uiso calc R 1 . .
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 0.0377(5) 0.0284(4) 0.0343(5) -0.0042(4) 0.0115(4) 0.0099(4)
    C1 0.0199(5) 0.0166(5) 0.0270(5) 0.0040(4) 0.0065(4) 0.0026(4)
    O2 0.0228(4) 0.0221(4) 0.0325(4) -0.0051(3) -0.0018(3) 0.0047(3)
    C2 0.0222(5) 0.0248(6) 0.0498(7) -0.0050(5) -0.0030(5) 0.0028(5)
    C3 0.0213(5) 0.0157(5) 0.0184(5) 0.0015(4) 0.0018(4) 0.0017(4)
    C4 0.0171(5) 0.0181(5) 0.0183(4) 0.0014(4) -0.0025(3) 0.0006(4)
    O3 0.0238(4) 0.0181(4) 0.0296(4) 0.0016(3) 0.0028(3) -0.0024(3)
    C5 0.0195(5) 0.0195(5) 0.0367(6) -0.0009(4) 0.0054(4) -0.0002(4)
    C6 0.0212(5) 0.0195(5) 0.0396(6) -0.0039(4) 0.0000(4) -0.0024(4)
    C7 0.0229(5) 0.0152(5) 0.0258(5) -0.0005(4) 0.0005(4) -0.0012(4)
    C8 0.0251(5) 0.0165(5) 0.0174(4) 0.0024(4) 0.0027(4) -0.0010(4)
    C9 0.0287(6) 0.0220(5) 0.0318(6) 0.0050(4) 0.0128(4) 0.0022(4)
    C10 0.0400(6) 0.0244(5) 0.0171(5) 0.0045(5) -0.0008(4) -0.0003(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.2015(13) ?
    C1 O2 . 1.3435(14) ?
    C1 C3 . 1.5027(14) ?
    O2 C2 . 1.4512(13) ?
    C2 H21 . 0.9800 ?
    C2 H22 . 0.9800 ?
    C2 H23 . 0.9800 ?
    C3 C4 . 1.4914(14) ?
    C3 C10 . 1.5281(14) ?
    C3 C8 . 1.5365(14) ?
    C4 O3 . 1.2230(13) ?
    C4 C5 . 1.5123(14) ?
    C5 C6 . 1.5300(16) ?
    C5 H51 . 0.9900 ?
    C5 H52 . 0.9900 ?
    C6 C7 . 1.5291(15) ?
    C6 H61 . 0.9900 ?
    C6 H62 . 0.9900 ?
    C7 C8 . 1.5143(15) ?
    C7 H71 . 0.9900 ?
    C7 H72 . 0.9900 ?
    C8 C10 . 1.4971(15) ?
    C8 C9 . 1.5143(15) ?
    C9 H91 . 0.9800 ?
    C9 H92 . 0.9800 ?
    C9 H93 . 0.9800 ?
    C10 H101 . 0.9900 ?
    C10 H102 . 0.9900 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 O2 . . 123.81(10) ?
    O1 C1 C3 . . 125.77(10) ?
    O2 C1 C3 . . 110.43(8) ?
    C1 O2 C2 . . 115.48(9) ?
    O2 C2 H21 . . 109.5 ?
    O2 C2 H22 . . 109.5 ?
    H21 C2 H22 . . 109.5 ?
    O2 C2 H23 . . 109.5 ?
    H21 C2 H23 . . 109.5 ?
    H22 C2 H23 . . 109.5 ?
    C4 C3 C1 . . 113.95(9) ?
    C4 C3 C10 . . 117.19(9) ?
    C1 C3 C10 . . 117.38(9) ?
    C4 C3 C8 . . 119.49(9) ?
    C1 C3 C8 . . 119.30(8) ?
    C10 C3 C8 . . 58.48(7) ?
    O3 C4 C3 . . 119.92(9) ?
    O3 C4 C5 . . 120.48(9) ?
    C3 C4 C5 . . 119.57(9) ?
    C4 C5 C6 . . 116.77(9) ?
    C4 C5 H51 . . 108.1 ?
    C6 C5 H51 . . 108.1 ?
    C4 C5 H52 . . 108.1 ?
    C6 C5 H52 . . 108.1 ?
    H51 C5 H52 . . 107.3 ?
    C7 C6 C5 . . 110.99(9) ?
    C7 C6 H61 . . 109.4 ?
    C5 C6 H61 . . 109.4 ?
    C7 C6 H62 . . 109.4 ?
    C5 C6 H62 . . 109.4 ?
    H61 C6 H62 . . 108.0 ?
    C8 C7 C6 . . 113.72(9) ?
    C8 C7 H71 . . 108.8 ?
    C6 C7 H71 . . 108.8 ?
    C8 C7 H72 . . 108.8 ?
    C6 C7 H72 . . 108.8 ?
    H71 C7 H72 . . 107.7 ?
    C10 C8 C9 . . 117.88(9) ?
    C10 C8 C7 . . 119.70(10) ?
    C9 C8 C7 . . 114.56(9) ?
    C10 C8 C3 . . 60.48(7) ?
    C9 C8 C3 . . 117.34(9) ?
    C7 C8 C3 . . 116.26(8) ?
    C8 C9 H91 . . 109.5 ?
    C8 C9 H92 . . 109.5 ?
    H91 C9 H92 . . 109.5 ?
    C8 C9 H93 . . 109.5 ?
    H91 C9 H93 . . 109.5 ?
    H92 C9 H93 . . 109.5 ?
    C8 C10 C3 . . 61.04(7) ?
    C8 C10 H101 . . 117.7 ?
    C3 C10 H101 . . 117.7 ?
    C8 C10 H102 . . 117.7 ?
    C3 C10 H102 . . 117.7 ?
    H101 C10 H102 . . 114.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 O2 C2 . . . . 3.52(15) ?
    C3 C1 O2 C2 . . . . -176.93(9) ?
    O1 C1 C3 C4 . . . . -114.23(12) ?
    O2 C1 C3 C4 . . . . 66.23(11) ?
    O1 C1 C3 C10 . . . . 28.26(15) ?
    O2 C1 C3 C10 . . . . -151.28(9) ?
    O1 C1 C3 C8 . . . . 95.65(13) ?
    O2 C1 C3 C8 . . . . -83.89(11) ?
    C1 C3 C4 O3 . . . . 20.08(13) ?
    C10 C3 C4 O3 . . . . -122.48(11) ?
    C8 C3 C4 O3 . . . . 170.13(9) ?
    C1 C3 C4 C5 . . . . -158.18(9) ?
    C10 C3 C4 C5 . . . . 59.25(13) ?
    C8 C3 C4 C5 . . . . -8.13(14) ?
    O3 C4 C5 C6 . . . . 170.06(10) ?
    C3 C4 C5 C6 . . . . -11.69(14) ?
    C4 C5 C6 C7 . . . . 43.31(14) ?
    C5 C6 C7 C8 . . . . -56.65(13) ?
    C6 C7 C8 C10 . . . . -31.53(13) ?
    C6 C7 C8 C9 . . . . 179.96(9) ?
    C6 C7 C8 C3 . . . . 37.91(13) ?
    C4 C3 C8 C10 . . . . 105.60(11) ?
    C1 C3 C8 C10 . . . . -105.94(11) ?
    C4 C3 C8 C9 . . . . -146.20(9) ?
    C1 C3 C8 C9 . . . . 2.26(13) ?
    C10 C3 C8 C9 . . . . 108.20(11) ?
    C4 C3 C8 C7 . . . . -5.22(13) ?
    C1 C3 C8 C7 . . . . 143.23(9) ?
    C10 C3 C8 C7 . . . . -110.83(11) ?
    C9 C8 C10 C3 . . . . -107.30(10) ?
    C7 C8 C10 C3 . . . . 105.21(10) ?
    C4 C3 C10 C8 . . . . -109.53(10) ?
    C1 C3 C10 C8 . . . . 109.20(10) ?
