##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Ethyl 2-(2-formylphenoxy)ethanoate--ethyl 2-(2-carboxyphenoxy)ethanoate
[0.682(7)/0.318(7)]
;
_chemical_name_common     ?
_chemical_formula_moiety     '0.682C11 H12 O4 , 0.318C11 H12 O5'
_chemical_formula_sum     'C11 H12 O4.32'
_chemical_formula_iupac     '0.682C11 H12 O4 , 0.318C11 H12 O5'
_chemical_formula_weight     213.29
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.8119(2)
_cell_length_b     13.8528(6)
_cell_length_c     15.6831(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1045.41(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1430
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.355
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     450
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.957
_exptl_absorpt_correction_T_max     0.993
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9977
_diffrn_reflns_av_R_equivalents     0.0463
_diffrn_reflns_av_sigmaI/netI     0.0355
_diffrn_reflns_theta_min     3.93
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     1419
_reflns_number_gt     1129
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0570
_refine_ls_R_factor_gt     0.0391
_refine_ls_wR_factor_gt     0.0887
_refine_ls_wR_factor_ref     0.0975
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     1419
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0559P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap and 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     0.185
_refine_diff_density_min     -0.231
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.031(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     none
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     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction
;
SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing,
1995)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
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
    C C1 0.3059(5) 0.92120(16) 0.70792(15) 0.0331(5) Uani d . 1 . .
    H H1 0.4298 0.9021 0.7520 0.040 Uiso d PR 0.682(7) C .
    C C2 0.0918(5) 0.85223(14) 0.67935(13) 0.0279(5) Uani d . 1 C .
    C C3 -0.0628(5) 0.87175(16) 0.60610(14) 0.0326(5) Uani d . 1 . .
    H H3 -0.0302 0.9299 0.5756 0.039 Uiso calc R 1 C .
    C C4 -0.2616(5) 0.80823(17) 0.57725(15) 0.0342(6) Uani d . 1 C .
    H H4 -0.3644 0.8221 0.5270 0.041 Uiso calc R 1 . .
    C C5 -0.3106(5) 0.72371(17) 0.62229(14) 0.0325(5) Uani d . 1 . .
    H H5 -0.4472 0.6796 0.6023 0.039 Uiso calc R 1 C .
    C C6 -0.1631(5) 0.70251(15) 0.69608(13) 0.0279(5) Uani d . 1 C .
    H H6 -0.2014 0.6452 0.7272 0.033 Uiso calc R 1 . .
    C C7 0.0399(4) 0.76560(15) 0.72365(13) 0.0257(5) Uani d . 1 . .
    C C8 0.1580(5) 0.66534(15) 0.84300(13) 0.0276(5) Uani d . 1 . .
    H H8A 0.1944 0.6077 0.8074 0.033 Uiso calc R 1 C .
    H H8B -0.0354 0.6621 0.8643 0.033 Uiso calc R 1 . .
    C C9 0.3585(4) 0.66947(15) 0.91613(13) 0.0276(5) Uani d . 1 B .
    C C10 0.4839(6) 0.5919(2) 1.04427(16) 0.0456(7) Uani d . 1 . .
    H H10A 0.5094 0.6564 1.0703 0.055 Uiso calc R 1 A 1
    H H10B 0.6683 0.5650 1.0294 0.055 Uiso calc R 1 A 1
    C C11A 0.324(3) 0.5233(10) 1.1055(6) 0.046(2) Uani d P 0.50(3) B 1
    H H11A 0.4306 0.5151 1.1582 0.068 Uiso calc PR 0.50(3) B 1
    H H11B 0.2988 0.4604 1.0780 0.068 Uiso calc PR 0.50(3) B 1
    H H11C 0.1419 0.5512 1.1188 0.068 Uiso calc PR 0.50(3) B 1
    C C11B 0.449(6) 0.5058(10) 1.0888(11) 0.065(5) Uani d P 0.50(3) B 2
    H H11D 0.5727 0.5053 1.1385 0.098 Uiso calc PR 0.50(3) B 2
    H H11E 0.4948 0.4514 1.0514 0.098 Uiso calc PR 0.50(3) B 2
    H H11F 0.2559 0.5003 1.1078 0.098 Uiso calc PR 0.50(3) B 2
    O O1 0.3320(3) 1.00164(11) 0.67838(12) 0.0434(5) Uani d . 1 C .
    O O2 0.4619(10) 0.9054(4) 0.7772(3) 0.037(2) Uani d P 0.318(7) C 3
    H H2 0.4288 0.8436 0.8074 0.045 Uiso d PR 0.318(7) C 3
    O O3 0.1994(3) 0.75114(10) 0.79483(9) 0.0306(4) Uani d . 1 C .
    O O4 0.5400(3) 0.72816(12) 0.92481(11) 0.0384(4) Uani d . 1 . .
    O O5 0.3060(3) 0.59732(10) 0.96963(9) 0.0321(4) Uani d . 1 B .
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
    C1 0.0332(12) 0.0300(12) 0.0360(12) 0.0012(10) 0.0098(11) -0.0001(10)
    C2 0.0286(11) 0.0231(10) 0.0319(11) 0.0051(9) 0.0095(9) -0.0015(10)
    C3 0.0343(12) 0.0319(12) 0.0316(12) 0.0089(10) 0.0067(10) 0.0057(10)
    C4 0.0314(12) 0.0395(13) 0.0316(11) 0.0059(11) 0.0005(10) 0.0045(10)
    C5 0.0274(11) 0.0344(12) 0.0357(12) -0.0015(11) -0.0010(10) -0.0042(10)
    C6 0.0271(11) 0.0235(10) 0.0330(11) -0.0008(9) 0.0027(10) 0.0001(9)
    C7 0.0261(11) 0.0240(11) 0.0271(11) 0.0053(9) 0.0039(9) -0.0013(9)
    C8 0.0277(11) 0.0257(11) 0.0296(11) 0.0018(10) 0.0022(9) 0.0016(9)
    C9 0.0235(10) 0.0280(11) 0.0314(11) 0.0047(10) 0.0017(10) -0.0015(9)
    C10 0.0481(15) 0.0493(15) 0.0395(14) 0.0060(13) -0.0176(12) 0.0030(13)
    C11A 0.043(5) 0.061(5) 0.033(3) -0.003(4) -0.007(4) 0.009(3)
    C11B 0.089(12) 0.050(5) 0.057(6) -0.013(6) -0.040(7) 0.016(4)
    O1 0.0448(10) 0.0260(8) 0.0595(11) -0.0027(8) 0.0151(10) 0.0015(8)
    O2 0.033(3) 0.034(3) 0.045(4) -0.008(2) -0.002(2) 0.008(2)
    O3 0.0330(9) 0.0288(8) 0.0300(8) -0.0045(7) -0.0035(7) 0.0051(6)
    O4 0.0288(9) 0.0407(9) 0.0456(9) -0.0056(8) -0.0043(8) 0.0014(8)
    O5 0.0359(9) 0.0298(8) 0.0306(8) 0.0015(7) -0.0069(7) 0.0017(7)
_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
    C1 O1 . 1.213(3) ?
    C1 O2 . 1.339(5) ?
    C1 C2 . 1.475(3) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.395(3) ?
    C2 C7 . 1.409(3) ?
    C3 C4 . 1.377(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.388(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.389(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.380(3) ?
    C6 H6 . 0.9500 ?
    C7 O3 . 1.369(3) ?
    C8 O3 . 1.422(2) ?
    C8 C9 . 1.500(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 O4 . 1.201(3) ?
    C9 O5 . 1.329(3) ?
    C10 C11B . 1.392(11) ?
    C10 O5 . 1.452(3) ?
    C10 C11A . 1.555(10) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11A H11A . 0.9800 ?
    C11A H11B . 0.9800 ?
    C11A H11C . 0.9800 ?
    C11B H11D . 0.9800 ?
    C11B H11E . 0.9800 ?
    C11B H11F . 0.9800 ?
    O2 H2 . 0.9903 ?
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 . . 113.7(3) ?
    O1 C1 C2 . . 123.5(2) ?
    O2 C1 C2 . . 122.2(3) ?
    O1 C1 H1 . . 117.9 ?
    C2 C1 H1 . . 118.6 ?
    C3 C2 C7 . . 118.5(2) ?
    C3 C2 C1 . . 119.8(2) ?
    C7 C2 C1 . . 121.7(2) ?
    C4 C3 C2 . . 121.2(2) ?
    C4 C3 H3 . . 119.4 ?
    C2 C3 H3 . . 119.4 ?
    C3 C4 C5 . . 119.3(2) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 121.0(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C7 C6 C5 . . 119.3(2) ?
    C7 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    O3 C7 C6 . . 124.01(18) ?
    O3 C7 C2 . . 115.30(19) ?
    C6 C7 C2 . . 120.7(2) ?
    O3 C8 C9 . . 106.51(17) ?
    O3 C8 H8A . . 110.4 ?
    C9 C8 H8A . . 110.4 ?
    O3 C8 H8B . . 110.4 ?
    C9 C8 H8B . . 110.4 ?
    H8A C8 H8B . . 108.6 ?
    O4 C9 O5 . . 125.2(2) ?
    O4 C9 C8 . . 125.47(19) ?
    O5 C9 C8 . . 109.36(17) ?
    C11B C10 O5 . . 112.2(5) ?
    C11B C10 C11A . . 26.8(9) ?
    O5 C10 C11A . . 103.7(4) ?
    C11B C10 H10A . . 125.6 ?
    O5 C10 H10A . . 111.0 ?
    C11A C10 H10A . . 111.0 ?
    C11B C10 H10B . . 84.4 ?
    O5 C10 H10B . . 111.0 ?
    C11A C10 H10B . . 111.0 ?
    H10A C10 H10B . . 109.0 ?
    C10 C11A H11A . . 109.5 ?
    C10 C11A H11B . . 109.5 ?
    H11A C11A H11B . . 109.5 ?
    C10 C11A H11C . . 109.5 ?
    H11A C11A H11C . . 109.5 ?
    H11B C11A H11C . . 109.5 ?
    C10 C11B H11D . . 109.5 ?
    C10 C11B H11E . . 109.5 ?
    H11D C11B H11E . . 109.5 ?
    C10 C11B H11F . . 109.5 ?
    H11D C11B H11F . . 109.5 ?
    H11E C11B H11F . . 109.5 ?
    C1 O2 H2 . . 116.0 ?
    C7 O3 C8 . . 118.48(17) ?
    C9 O5 C10 . . 115.81(18) ?
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 C2 C3 . . . . 10.7(3) ?
    O2 C1 C2 C3 . . . . -179.3(3) ?
    O1 C1 C2 C7 . . . . -170.1(2) ?
    O2 C1 C2 C7 . . . . 0.0(4) ?
    C7 C2 C3 C4 . . . . 0.0(3) ?
    C1 C2 C3 C4 . . . . 179.2(2) ?
    C2 C3 C4 C5 . . . . 0.5(3) ?
    C3 C4 C5 C6 . . . . 0.3(3) ?
    C4 C5 C6 C7 . . . . -1.6(3) ?
    C5 C6 C7 O3 . . . . -179.22(18) ?
    C5 C6 C7 C2 . . . . 2.1(3) ?
    C3 C2 C7 O3 . . . . 179.91(18) ?
    C1 C2 C7 O3 . . . . 0.7(3) ?
    C3 C2 C7 C6 . . . . -1.3(3) ?
    C1 C2 C7 C6 . . . . 179.48(19) ?
    O3 C8 C9 O4 . . . . -8.5(3) ?
    O3 C8 C9 O5 . . . . 172.12(16) ?
    C6 C7 O3 C8 . . . . 1.0(3) ?
    C2 C7 O3 C8 . . . . 179.79(18) ?
    C9 C8 O3 C7 . . . . -179.91(17) ?
    O4 C9 O5 C10 . . . . 0.8(3) ?
    C8 C9 O5 C10 . . . . -179.85(18) ?
    C11B C10 O5 C9 . . . . -169.3(15) ?
    C11A C10 O5 C9 . . . . 163.9(6) ?
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
    O2 H2 O3 . 0.99 1.70 2.497(5) 134
    O2 H2 O4 . 0.99 2.50 3.395(5) 151
    C6 H6 O1 3_546 0.95 2.56 3.504(3) 174
    C8 H8B O4 1_455 0.99 2.43 3.354(3) 155
data_global
_journal_date_recd_electronic     2007-02-14
_journal_date_accepted     2007-02-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1426
_journal_page_last     o1427
_journal_paper_category     EO
_journal_coeditor_code     BT2273
_publ_contact_author_name     'William T. A. Harrison'
_publ_contact_author_address
;
Department of Chemistry
University of Aberdeen
Aberdeen AB24 3UE
Scotland
;
_publ_contact_author_email     w.harrison@abdn.ac.uk
_publ_contact_author_fax     '44 1224 272921'
_publ_contact_author_phone     '44 1224 272897'
_publ_section_title
;
Ethyl 2-(2-formylphenoxy)ethanoate--ethyl 2-(2-carboxyphenoxy)ethanoate
[0.682(7)/0.318(7)]
;
loop_
    _publ_author_name
    _publ_author_address
    'Williamson, Craig'
;
Department of Chemistry
University of Aberdeen
Meston Walk
Aberdeen AB24 3UE
Scotland
;
    'Storey, John M. D.'
;
Department of Chemistry
University of Aberdeen
Meston Walk
Aberdeen AB24 3UE
Scotland
;
    'Harrison, William T. A.'
;
Department of Chemistry
University of Aberdeen
Meston Walk
Aberdeen AB24 3UE
Scotland
;
