##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 2-(3-acetyl-6-methyl-2-oxo-2H-pyran-4-yloxy)acetate
;
_chemical_name_common        .0403
_chemical_formula_moiety     'C12 H14 O6'
_chemical_formula_sum     'C12 H14 O6'
_chemical_formula_iupac     'C12 H14 O6'
_chemical_formula_weight     254.23
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.8258(10)
_cell_length_b     8.2722(11)
_cell_length_c     10.0838(13)
_cell_angle_alpha     77.374(7)
_cell_angle_beta     77.759(6)
_cell_angle_gamma     88.857(7)
_cell_volume     622.28(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     6664
_cell_measurement_theta_min     2.12
_cell_measurement_theta_max     28.28
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'rectangular prism'
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.72
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.357
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     268
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.9249
_exptl_absorpt_correction_T_max     0.9881
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII'
_diffrn_measurement_method     'φ scans and ω scans with κ offsets'
_diffrn_detector_area_resol_mean     83.33
_diffrn_reflns_number     14279
_diffrn_reflns_av_R_equivalents     0.0355
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     28.28
_diffrn_reflns_theta_full     28.28
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_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 >
2σ(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     3039
_reflns_number_gt     2330
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0635
_refine_ls_R_factor_gt     0.0502
_refine_ls_wR_factor_gt     0.1440
_refine_ls_wR_factor_ref     0.1589
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     3039
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0773P)²+0.1512P] 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     0.346
_refine_diff_density_min     -0.204
_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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2008)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
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 0.57091(13) 0.60585(14) 1.11130(11) 0.0528(3) Uani d . 1 . .
    C C2 0.44227(18) 0.6846(2) 1.04378(17) 0.0494(4) Uani d . 1 . .
    C C3 0.50118(17) 0.81700(18) 0.92489(15) 0.0438(3) Uani d . 1 . .
    C C4 0.67613(17) 0.86621(18) 0.89085(15) 0.0419(3) Uani d . 1 . .
    C C5 0.79728(17) 0.78287(18) 0.96663(16) 0.0445(3) Uani d . 1 . .
    H H5 0.9142 0.8175 0.9433 0.053 Uiso calc R 1 . .
    C C6 0.74139(18) 0.65385(19) 1.07210(15) 0.0453(3) Uani d . 1 . .
    C C6A 0.8505(2) 0.5494(2) 1.15859(19) 0.0626(5) Uani d . 1 . .
    H H6A1 0.9708 0.5851 1.1248 0.094 Uiso calc R 1 . .
    H H6A2 0.8379 0.4358 1.1537 0.094 Uiso calc R 1 . .
    H H6A3 0.8134 0.5597 1.2534 0.094 Uiso calc R 1 . .
    C C3A 0.36798(19) 0.8935(2) 0.84701(18) 0.0525(4) Uani d . 1 . .
    C C3B 0.4174(3) 0.9705(5) 0.6972(3) 0.1171(12) Uani d . 1 . .
    H H3B1 0.3199 0.9630 0.6548 0.176 Uiso calc R 1 . .
    H H3B2 0.5145 0.9138 0.6542 0.176 Uiso calc R 1 . .
    H H3B3 0.4499 1.0849 0.6854 0.176 Uiso calc R 1 . .
    O O3A 0.21609(15) 0.8898(2) 0.90547(17) 0.0803(5) Uani d . 1 . .
    O O4 0.72493(13) 0.99457(14) 0.78399(13) 0.0576(3) Uani d . 1 . .
    C C1A 0.9346(2) 1.1577(2) 0.60243(17) 0.0525(4) Uani d . 1 . .
    C C2A 0.8981(2) 1.0641(2) 0.74992(18) 0.0562(4) Uani d . 1 . .
    H H2A1 0.9816 0.9768 0.7622 0.067 Uiso calc R 1 . .
    H H2A2 0.9088 1.1378 0.8106 0.067 Uiso calc R 1 . .
    O O2 0.29702(14) 0.62711(18) 1.09368(15) 0.0704(4) Uani d . 1 . .
    O O1A 0.8501(2) 1.1503(2) 0.51873(16) 0.0947(6) Uani d . 1 . .
    O O1B 1.08032(15) 1.24797(15) 0.57701(11) 0.0587(3) Uani d . 1 . .
    C C1E 1.1521(3) 1.3319(3) 0.43439(19) 0.0748(6) Uani d . 1 . .
    H H1E1 1.0694 1.4101 0.3996 0.090 Uiso calc R 1 . .
    H H1E2 1.1769 1.2523 0.3755 0.090 Uiso calc R 1 . .
    C C2E 1.3156(3) 1.4200(4) 0.4343(3) 0.1057(9) Uani d . 1 . .
    H H2E1 1.2882 1.5037 0.4875 0.159 Uiso calc R 1 . .
    H H2E2 1.3712 1.4710 0.3404 0.159 Uiso calc R 1 . .
    H H2E3 1.3930 1.3424 0.4747 0.159 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 0.0358(5) 0.0632(7) 0.0518(6) -0.0105(5) -0.0048(4) 0.0003(5)
    C2 0.0325(7) 0.0602(9) 0.0533(8) -0.0079(6) -0.0035(6) -0.0126(7)
    C3 0.0282(6) 0.0524(8) 0.0514(8) -0.0040(6) -0.0069(6) -0.0141(6)
    C4 0.0306(6) 0.0461(7) 0.0475(7) -0.0052(5) -0.0062(5) -0.0084(6)
    C5 0.0280(6) 0.0528(8) 0.0512(8) -0.0071(5) -0.0080(5) -0.0077(6)
    C6 0.0338(7) 0.0543(8) 0.0469(7) -0.0054(6) -0.0076(6) -0.0096(6)
    C6A 0.0500(9) 0.0741(11) 0.0578(10) -0.0051(8) -0.0168(7) 0.0039(8)
    C3A 0.0312(7) 0.0618(9) 0.0665(10) -0.0022(6) -0.0129(6) -0.0156(8)
    C3B 0.0486(11) 0.212(3) 0.0718(14) 0.0101(15) -0.0214(10) 0.0165(17)
    O3A 0.0314(6) 0.1083(11) 0.0932(10) 0.0034(6) -0.0130(6) -0.0053(8)
    O4 0.0332(5) 0.0616(7) 0.0687(7) -0.0110(5) -0.0157(5) 0.0110(5)
    C1A 0.0461(8) 0.0541(9) 0.0544(9) -0.0057(7) -0.0108(7) -0.0052(7)
    C2A 0.0361(7) 0.0655(10) 0.0578(9) -0.0158(7) -0.0116(6) 0.0090(7)
    O2 0.0346(6) 0.0894(9) 0.0752(8) -0.0196(6) -0.0017(5) -0.0007(7)
    O1A 0.0861(11) 0.1290(14) 0.0670(9) -0.0384(10) -0.0321(8) 0.0022(9)
    O1B 0.0544(7) 0.0653(7) 0.0469(6) -0.0197(5) -0.0051(5) 0.0040(5)
    C1E 0.0799(13) 0.0853(13) 0.0456(9) -0.0179(10) -0.0010(9) 0.0044(9)
    C2E 0.0910(17) 0.127(2) 0.0702(13) -0.0493(15) 0.0077(12) 0.0197(13)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C6 . 1.3501(16) ?
    O1 C2 . 1.404(2) ?
    C2 O2 . 1.2024(17) ?
    C2 C3 . 1.436(2) ?
    C3 C4 . 1.3856(17) ?
    C3 C3A . 1.486(2) ?
    C4 O4 . 1.3326(18) ?
    C4 C5 . 1.417(2) ?
    C5 C6 . 1.337(2) ?
    C5 H5 . 0.9300 ?
    C6 C6A . 1.481(2) ?
    C6A H6A1 . 0.9600 ?
    C6A H6A2 . 0.9600 ?
    C6A H6A3 . 0.9600 ?
    C3A O3A . 1.2073(19) ?
    C3A C3B . 1.476(3) ?
    C3B H3B1 . 0.9600 ?
    C3B H3B2 . 0.9600 ?
    C3B H3B3 . 0.9600 ?
    O4 C2A . 1.4256(17) ?
    C1A O1A . 1.189(2) ?
    C1A O1B . 1.3228(18) ?
    C1A C2A . 1.489(2) ?
    C2A H2A1 . 0.9700 ?
    C2A H2A2 . 0.9700 ?
    O1B C1E . 1.450(2) ?
    C1E C2E . 1.485(3) ?
    C1E H1E1 . 0.9700 ?
    C1E H1E2 . 0.9700 ?
    C2E H2E1 . 0.9600 ?
    C2E H2E2 . 0.9600 ?
    C2E H2E3 . 0.9600 ?
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
    C6 O1 C2 . . 122.89(12) ?
    O2 C2 O1 . . 113.96(15) ?
    O2 C2 C3 . . 129.34(16) ?
    O1 C2 C3 . . 116.68(12) ?
    C4 C3 C2 . . 118.59(13) ?
    C4 C3 C3A . . 124.32(14) ?
    C2 C3 C3A . . 117.09(12) ?
    O4 C4 C3 . . 117.09(13) ?
    O4 C4 C5 . . 121.74(12) ?
    C3 C4 C5 . . 121.17(13) ?
    C6 C5 C4 . . 119.19(12) ?
    C6 C5 H5 . . 120.4 ?
    C4 C5 H5 . . 120.4 ?
    C5 C6 O1 . . 121.31(13) ?
    C5 C6 C6A . . 126.34(14) ?
    O1 C6 C6A . . 112.35(13) ?
    C6 C6A H6A1 . . 109.5 ?
    C6 C6A H6A2 . . 109.5 ?
    H6A1 C6A H6A2 . . 109.5 ?
    C6 C6A H6A3 . . 109.5 ?
    H6A1 C6A H6A3 . . 109.5 ?
    H6A2 C6A H6A3 . . 109.5 ?
    O3A C3A C3B . . 118.99(17) ?
    O3A C3A C3 . . 119.99(16) ?
    C3B C3A C3 . . 120.99(14) ?
    C3A C3B H3B1 . . 109.5 ?
    C3A C3B H3B2 . . 109.5 ?
    H3B1 C3B H3B2 . . 109.5 ?
    C3A C3B H3B3 . . 109.5 ?
    H3B1 C3B H3B3 . . 109.5 ?
    H3B2 C3B H3B3 . . 109.5 ?
    C4 O4 C2A . . 121.02(12) ?
    O1A C1A O1B . . 124.77(16) ?
    O1A C1A C2A . . 126.07(16) ?
    O1B C1A C2A . . 109.14(14) ?
    O4 C2A C1A . . 108.53(13) ?
    O4 C2A H2A1 . . 110.0 ?
    C1A C2A H2A1 . . 110.0 ?
    O4 C2A H2A2 . . 110.0 ?
    C1A C2A H2A2 . . 110.0 ?
    H2A1 C2A H2A2 . . 108.4 ?
    C1A O1B C1E . . 117.97(14) ?
    O1B C1E C2E . . 107.09(17) ?
    O1B C1E H1E1 . . 110.3 ?
    C2E C1E H1E1 . . 110.3 ?
    O1B C1E H1E2 . . 110.3 ?
    C2E C1E H1E2 . . 110.3 ?
    H1E1 C1E H1E2 . . 108.6 ?
    C1E C2E H2E1 . . 109.5 ?
    C1E C2E H2E2 . . 109.5 ?
    H2E1 C2E H2E2 . . 109.5 ?
    C1E C2E H2E3 . . 109.5 ?
    H2E1 C2E H2E3 . . 109.5 ?
    H2E2 C2E H2E3 . . 109.5 ?
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
    C6 O1 C2 O2 . . . . -179.01(14) ?
    C6 O1 C2 C3 . . . . 2.6(2) ?
    O2 C2 C3 C4 . . . . 177.25(16) ?
    O1 C2 C3 C4 . . . . -4.6(2) ?
    O2 C2 C3 C3A . . . . -2.2(3) ?
    O1 C2 C3 C3A . . . . 175.96(13) ?
    C2 C3 C4 O4 . . . . -176.87(13) ?
    C3A C3 C4 O4 . . . . 2.5(2) ?
    C2 C3 C4 C5 . . . . 3.3(2) ?
    C3A C3 C4 C5 . . . . -177.39(14) ?
    O4 C4 C5 C6 . . . . -179.39(14) ?
    C3 C4 C5 C6 . . . . 0.5(2) ?
    C4 C5 C6 O1 . . . . -2.8(2) ?
    C4 C5 C6 C6A . . . . 177.66(16) ?
    C2 O1 C6 C5 . . . . 1.2(2) ?
    C2 O1 C6 C6A . . . . -179.19(14) ?
    C4 C3 C3A O3A . . . . -153.29(17) ?
    C2 C3 C3A O3A . . . . 26.1(2) ?
    C4 C3 C3A C3B . . . . 28.5(3) ?
    C2 C3 C3A C3B . . . . -152.2(2) ?
    C3 C4 O4 C2A . . . . 173.81(14) ?
    C5 C4 O4 C2A . . . . -6.3(2) ?
    C4 O4 C2A C1A . . . . 159.18(14) ?
    O1A C1A C2A O4 . . . . -13.5(3) ?
    O1B C1A C2A O4 . . . . 168.37(13) ?
    O1A C1A O1B C1E . . . . -6.2(3) ?
    C2A C1A O1B C1E . . . . 172.01(16) ?
    C1A O1B C1E C2E . . . . -178.72(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C6A H6A1 O2 1_655 0.9600 2.5300 3.462(2) 165.00 yes
    C5 H5 O3A 1_655 0.9300 2.3800 3.3053(19) 174.00 yes
    C2A H2A1 O3A 1_655 0.9700 2.5700 3.355(2) 138.00 yes
    C2E H2E2 O1 1_664 0.9600 2.5400 3.484(3) 169.00 yes
data_global
_journal_date_recd_electronic     2010-01-12
_journal_date_accepted     2010-01-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o397
_journal_page_last     o397
_journal_paper_category     QO
_journal_coeditor_code     BT5170
_publ_contact_author_name     'Dr. Muhammad Raza Shah'
_publ_contact_author_address
;
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi, Karachi- 75270, Pakistan
;
_publ_contact_author_email     'raza_shahm@yahoo.com'
_publ_contact_author_fax     '+92-21-4819018-19'
_publ_contact_author_phone     '+92-21-4824934, Ext233, UAN 111-222-292'
_publ_section_title
;
Ethyl 2-(3-acetyl-6-methyl-2-oxo-2H-pyran-4-yloxy)acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Rabnawaz, Muhammad'
;
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi, Karachi 75270, Pakistan
;
    'Stacy D. Benson'
;
Oklahoma State University
Department of Chemistry
107 Physical Sciences
Stillwater, OK 74078-3071
USA
;
    'Khan, Burhan'
;
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi, Karachi 75270, Pakistan
;
    'Shah, Muhammad Raza'
;
H.E.J. Research Institute of Chemistry
International Center for Chemical and Biological Sciences
University of Karachi, Karachi 75270, Pakistan
;
_publ_section_synopsis     .
