##############################################################################
###                                                                        ###
###        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                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2001-05-14
_journal_date_accepted     2001-06-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      8
_journal_page_first     o669
_journal_page_last     o671
_journal_paper_category     EO
_publ_contact_author_name     'Arvid Mostad'
_publ_contact_author_address
;
Department of Chemistry
University of Oslo
PO Box 1033 Blindern
N-0315 Oslo, Norway
;
_publ_contact_author_email     arvidm@kjemi.uio.no
_publ_contact_author_fax     '+47 22 85 54 41'
_publ_contact_author_phone     '+47 22 85 54 15'
_publ_section_title
;
Ethyl 2-trans-cinnamonylacetoacetate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Arrieta, Antonio F. '
; ?
;
;Institute for Organic Catalysis Research
University of Rostock
Buchbinderstraße 5-6
D-18051 Rostock
Germany
;
    'Arvid Mostad'
; ?
;
; Department of Chemistry
University of Oslo
PO Box 1033 Blindern
N-0315 Oslo
Norway
;
data_I
_chemical_name_systematic
;
2-acetyl-3-oxo-5-pentyl-pent-4-enoic acid ethyl ester
;
_chemical_name_common     '2-trans-cinnamonyl-acetoacetic acid'
_chemical_formula_moiety     'C15 H16 O4'
_chemical_formula_sum     'C15 H16 O4'
_chemical_formula_iupac     'C15 H16 O4'
_chemical_formula_weight     260.28
_chemical_melting_point     45
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P n n 2'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x+1/2, -y+1/2, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     21.698(4)
_cell_length_b     7.3390(15)
_cell_length_c     8.6380(17)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1375.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1024
_cell_measurement_theta_min     3.7
_cell_measurement_theta_max     26.3
_cell_measurement_temperature     123(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max      .4
_exptl_crystal_size_mid      .3
_exptl_crystal_size_min      .3
_exptl_crystal_density_diffrn     1.257
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu      .091
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min      .9642
_exptl_absorpt_correction_T_max      .9730
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8
_diffrn_reflns_number     13464
_diffrn_reflns_av_R_equivalents      .0240
_diffrn_reflns_av_sigmaI/netI      .0122
_diffrn_reflns_theta_min     2.54
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_theta_full     26.38
_diffrn_measured_fraction_theta_max      .998
_diffrn_measured_fraction_theta_full      .998
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     26
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_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     2813
_reflns_number_gt     2703
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0331
_refine_ls_R_factor_gt      .0313
_refine_ls_wR_factor_ref      .0789
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     2813
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.038P)²+0.275P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .128
_refine_diff_density_min      -.164
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXL97'
_computing_publication_material     'SHELXL97'
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
    C4  .54666(6)  .30193(18)  .76650(17)  .0281(3) Uani d . 1 . . C
    O1  .43932(5)  .18041(16)  .90040(12)  .0424(3) Uani d . 1 . . O
    O2  .54340(5)  .29967(15)  .91770(12)  .0377(2) Uani d . 1 . . O
    C2  .44083(6)  .18612(18)  .75416(17)  .0303(3) Uani d . 1 . . C
    C3  .49602(6)  .24780(18)  .67582(18)  .0267(3) Uani d . 1 . . C
    C6  .65241(6)  .41141(19)  .79130(17)  .0311(3) Uani d . 1 . . C
    C5  .60448(6)  .36803(18)  .70073(16)  .0290(3) Uani d . 1 . . C
    C7  .71294(7)  .47571(18)  .73952(18)  .0319(3) Uani d . 1 . . C
    C1  .38516(7)  .1190(2)  .6689(2)  .0358(3) Uani d . 1 . . C
    C10  .82952(8)  .6003(2)  .6492(3)  .0489(4) Uani d . 1 . . C
    C8  .72895(8)  .4860(3)  .5835(2)  .0445(4) Uani d . 1 . . C
    C12  .75629(8)  .5312(2)  .8491(2)  .0435(4) Uani d . 1 . . C
    C9  .78637(9)  .5492(3)  .5391(3)  .0557(5) Uani d . 1 . . C
    C11  .81407(8)  .5933(3)  .8036(3)  .0508(5) Uani d . 1 . . C
    O4  .44910(4)  .31302(13)  .43790(11)  .0308(2) Uani d . 1 . . O
    O3  .54393(4)  .19264(14)  .43011(12)  .0344(2) Uani d . 1 . . O
    C14  .44371(7)  .2908(2)  .27055(18)  .0345(3) Uani d . 1 . . C
    C13  .50018(6)  .24626(17)  .50386(17)  .0260(3) Uani d . 1 . . C
    H8  .6985(12)  .452(3)  .501(3)  .074(7) Uiso d . 1 . . H
    H5  .6058(7)  .377(2)  .5859(19)  .026(4) Uiso d . 1 . . H
    H14B  .4419(8)  .161(3)  .250(2)  .035(4) Uiso d . 1 . . H
    H14A  .4806(8)  .345(2)  .223(2)  .038(4) Uiso d . 1 . . H
    H1C  .3631(9)  .221(3)  .625(2)  .045(5) Uiso d . 1 . . H
    H12  .7451(9)  .526(3)  .951(3)  .049(5) Uiso d . 1 . . H
    H1A  .3583(11)  .053(3)  .735(3)  .063(6) Uiso d . 1 . . H
    H9  .7968(10)  .543(3)  .419(3)  .066(6) Uiso d . 1 . . H
    C15  .38452(9)  .3814(3)  .2225(2)  .0466(4) Uani d . 1 . . C
    H15C  .3873(10)  .511(3)  .244(3)  .062(6) Uiso d . 1 . . H
    H6  .6492(7)  .4027(19)  .9022(19)  .022(3) Uiso d . 1 . . H
    H15B  .3481(10)  .326(3)  .281(2)  .058(6) Uiso d . 1 . . H
    H10  .8709(10)  .640(3)  .617(2)  .049(5) Uiso d . 1 . . H
    H11  .8433(10)  .633(3)  .882(3)  .060(6) Uiso d . 1 . . H
    H1B  .3938(9)  .039(3)  .582(2)  .051(5) Uiso d . 1 . . H
    H15A  .3773(10)  .370(3)  .101(3)  .060(6) Uiso d . 1 . . H
    H2  .4992(12)  .255(3)  .938(3)  .080(8) Uiso d . 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
    C4  .0276(6)  .0258(6)  .0309(6)  .0030(5)  .0003(5)  -.0003(5)
    O1  .0383(6)  .0518(7)  .0373(6)  -.0041(5)  .0098(5)  .0029(5)
    O2  .0348(5)  .0486(6)  .0296(5)  -.0033(5)  .0003(4)  .0004(5)
    C2  .0290(6)  .0269(6)  .0350(7)  .0015(5)  .0059(6)  .0006(5)
    C3  .0257(6)  .0225(6)  .0320(6)  .0021(5)  .0022(5)  .0000(5)
    C6  .0303(7)  .0288(6)  .0343(7)  .0022(5)  -.0005(6)  .0003(6)
    C5  .0270(7)  .0267(6)  .0333(7)  .0015(5)  .0008(5)  .0009(5)
    C7  .0283(7)  .0271(7)  .0404(8)  .0036(5)  -.0031(6)  -.0001(6)
    C1  .0278(7)  .0343(7)  .0452(8)  -.0037(6)  .0057(6)  .0012(7)
    C10  .0267(8)  .0424(9)  .0777(12)  -.0027(7)  .0051(8)  .0064(8)
    C8  .0370(8)  .0527(9)  .0439(8)  -.0039(7)  .0028(7)  -.0077(7)
    C12  .0374(8)  .0486(10)  .0444(8)  -.0040(7)  -.0075(7)  .0052(7)
    C9  .0439(9)  .0635(11)  .0596(11)  -.0082(9)  .0156(8)  -.0057(9)
    C11  .0332(8)  .0457(9)  .0734(13)  -.0051(7)  -.0155(8)  .0077(8)
    O4  .0288(5)  .0349(5)  .0288(5)  .0034(4)  .0003(4)  -.0018(4)
    O3  .0269(5)  .0436(6)  .0326(5)  .0027(4)  .0031(4)  -.0041(4)
    C14  .0350(7)  .0399(8)  .0286(7)  .0012(6)  .0001(6)  -.0022(6)
    C13  .0233(6)  .0235(6)  .0312(6)  -.0016(5)  .0009(5)  -.0009(5)
    C15  .0508(10)  .0535(10)  .0355(8)  .0143(8)  -.0076(7)  -.0009(8)
_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
    C4 O2 . 1.3081(18) y
    C4 C3 . 1.4066(19) y
    C4 C5 . 1.4601(18) y
    O1 C2 . 1.2643(18) y
    O1 H2 . 1.45(3) y
    O2 H2 . 1.03(3) y
    C2 C3 . 1.4481(19) y
    C2 C1 . 1.498(2) y
    C3 C13 . 1.4882(18) y
    C6 C5 . 1.3398(19) y
    C6 C7 . 1.466(2) y
    C6 H6 .  .963(16) n
    C5 H5 .  .994(16) n
    C7 C8 . 1.394(2) n
    C7 C12 . 1.395(2) n
    C1 H1C .  .96(2) n
    C1 H1A .  .95(2) n
    C1 H1B .  .97(2) n
    C10 C11 . 1.376(3) n
    C10 C9 . 1.386(3) n
    C10 H10 .  .98(2) n
    C8 C9 . 1.384(2) n
    C8 H8 . 1.00(3) n
    C12 C11 . 1.391(2) n
    C12 H12 .  .92(2) n
    C9 H9 . 1.06(2) n
    C11 H11 .  .97(2) n
    O4 C13 . 1.3390(16) y
    O4 C14 . 1.4594(18) y
    O3 C13 . 1.2091(17) y
    C14 C15 . 1.505(2) y
    C14 H14B .  .972(18) n
    C14 H14A .  .986(18) n
    C15 H15C .  .97(2) n
    C15 H15B . 1.02(2) n
    C15 H15A . 1.07(2) n
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
    O2 C4 C3 . . 120.67(13) y
    O2 C4 C5 . . 116.06(12) y
    C3 C4 C5 . . 123.25(14) y
    C2 O1 H2 . . 101.0(11) y
    C4 O2 H2 . . 103.2(15) y
    O1 C2 C3 . . 119.92(14) y
    O1 C2 C1 . . 117.34(13) y
    C3 C2 C1 . . 122.68(14) y
    C4 C3 C2 . . 118.30(14) y
    C4 C3 C13 . . 120.71(12) y
    C2 C3 C13 . . 120.94(12) y
    C5 C6 C7 . . 126.44(14) y
    C5 C6 H6 . . 120.6(9) n
    C7 C6 H6 . . 113.0(9) n
    C6 C5 C4 . . 121.24(13) y
    C6 C5 H5 . . 122.9(9) n
    C4 C5 H5 . . 115.8(9) n
    C8 C7 C12 . . 118.16(15) n
    C8 C7 C6 . . 122.41(14) y
    C12 C7 C6 . . 119.42(14) y
    C2 C1 H1C . . 109.7(11) n
    C2 C1 H1A . . 111.5(14) n
    H1C C1 H1A . . 109.1(17) n
    C2 C1 H1B . . 115.0(12) n
    H1C C1 H1B . . 105.4(16) n
    H1A C1 H1B . . 105.9(17) n
    C11 C10 C9 . . 119.37(16) n
    C11 C10 H10 . . 120.5(11) n
    C9 C10 H10 . . 120.2(11) n
    C9 C8 C7 . . 120.73(17) n
    C9 C8 H8 . . 118.6(15) n
    C7 C8 H8 . . 120.6(15) ?
    C11 C12 C7 . . 120.78(18) n
    C11 C12 H12 . . 121.8(12) n
    C7 C12 H12 . . 117.4(12) n
    C8 C9 C10 . . 120.54(19) n
    C8 C9 H9 . . 116.7(12) n
    C10 C9 H9 . . 122.4(12) n
    C10 C11 C12 . . 120.39(17) n
    C10 C11 H11 . . 120.5(13) n
    C12 C11 H11 . . 119.1(13) n
    C13 O4 C14 . . 116.54(11) y
    O4 C14 C15 . . 106.98(13) y
    O4 C14 H14B . . 107.3(11) n
    C15 C14 H14B . . 110.3(10) n
    O4 C14 H14A . . 107.7(10) n
    C15 C14 H14A . . 113.4(10) n
    H14B C14 H14A . . 110.8(15) n
    O3 C13 O4 . . 123.01(13) y
    O3 C13 C3 . . 125.16(13) y
    O4 C13 C3 . . 111.83(11) y
    C14 C15 H15C . . 109.0(13) n
    C14 C15 H15B . . 110.3(12) n
    H15C C15 H15B . . 110.1(18) n
    C14 C15 H15A . . 111.3(12) n
    H15C C15 H15A . . 106.1(17) n
    H15B C15 H15A . . 109.9(16) n
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
    O2 C4 C3 C2 . . . . -1.27(19) n
    C5 C4 C3 C2 . . . . -179.44(12) n
    O2 C4 C3 C13 . . . . -178.58(12) n
    C5 C4 C3 C13 . . . . 3.2(2) n
    O1 C2 C3 C4 . . . .  -.7(2) n
    C1 C2 C3 C4 . . . . -177.69(13) n
    O1 C2 C3 C13 . . . . 176.65(12) n
    C1 C2 C3 C13 . . . .  -.4(2) n
    C7 C6 C5 C4 . . . . 178.81(12) n
    O2 C4 C5 C6 . . . . 4.40(19) n
    C3 C4 C5 C6 . . . . -177.34(13) n
    C5 C6 C7 C8 . . . . -5.0(2) n
    C5 C6 C7 C12 . . . . 174.17(15) n
    C12 C7 C8 C9 . . . .  .2(3) n
    C6 C7 C8 C9 . . . . 179.36(16) n
    C8 C7 C12 C11 . . . .  -.6(2) n
    C6 C7 C12 C11 . . . . -179.83(16) n
    C7 C8 C9 C10 . . . . 1.2(3) n
    C11 C10 C9 C8 . . . . -2.1(3) n
    C9 C10 C11 C12 . . . . 1.6(3) n
    C7 C12 C11 C10 . . . .  -.3(3) n
    C13 O4 C14 C15 . . . . -177.93(12) n
    C14 O4 C13 O3 . . . . 10.01(19) n
    C14 O4 C13 C3 . . . . -170.26(11) n
    C4 C3 C13 O3 . . . . 42.0(2) y
    C2 C3 C13 O3 . . . . -135.22(14) y
    C4 C3 C13 O4 . . . . -137.70(12) y
    C2 C3 C13 O4 . . . . 45.06(17) y
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
    O2 H2 O1 1_555 1.03(3) 1.45(3) 2.427(2) 157(2) yes
    C10 H10 O2 4_654  .98(2) 2.79(2) 3.707(2) 155(2) yes
    C11 H11 O3 4_655  .97(2) 2.52(2) 3.349(2) 143(2) yes
