##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-05-13
_journal_date_accepted     2007-05-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o3010
_journal_page_last     o3010
_journal_paper_category     QO
_journal_coeditor_code     CV2244
_publ_contact_author_name     'Dr. Zheng-Feng Xie'
_publ_contact_author_address
;
Department of chemistry, Key Laboratory of Oil and Gas Fine Chemicals,
Ministry of Education, Xinjiang University, Urumqi 830046, P.R. China
;
_publ_contact_author_email     xiezhf72@yahoo.com.cn
_publ_contact_author_fax     '+86-991-8581012-807'
_publ_contact_author_phone     '+86-991-8582807'
_publ_section_title
;
1-(5-Methyl-3-phenylisoxazol-4-yl)ethanone
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Zheng-Feng Xie'
;Key Laboratory of Oil and Gas Fine Chemicals,
Ministry of Education,
Xinjiang University,
Urumqi 830046,
People's Republic of China
;
    'Xue-Xia Mo'
;Key Laboratory of Oil and Gas Fine Chemicals,
Ministry of Education,
Xinjiang University,
Urumqi 830046,
People's Republic of China
;
    'Xue-Li Mo'
;The Fifth Middle School of Changji State,
Changji 831100,
People's Republic of China
;
    'Fang-Ming Liu'
;Chemistry Department of Hangzhou Teacher College,
Hangzhou 310012,
People's Republic of China
;
_publ_section_synopsis     .
data_I
_chemical_name_systematic
;
1-(5-methyl-3-phenylisoxazol-4-yl)ethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N O2'
_chemical_formula_sum     'C12 H11 N O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C12 H11 N O2'
_chemical_formula_weight     201.22
_chemical_melting_point     336
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     14.090(3)
_cell_length_b     5.2504(11)
_cell_length_c     14.280(3)
_cell_angle_alpha     90.00
_cell_angle_beta     92.60(3)
_cell_angle_gamma     90.00
_cell_volume     1055.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5329
_cell_measurement_theta_min     3.26
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.70
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.266
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
Higashi (1995)
;
_exptl_absorpt_correction_T_min     0.9416
_exptl_absorpt_correction_T_max     0.9828
_exptl_special_details
; ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Rotating Anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS SPIDER'
_diffrn_measurement_method     'ω oscillation'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10361
_diffrn_reflns_av_R_equivalents     0.0246
_diffrn_reflns_av_sigmaI/netI     0.0221
_diffrn_reflns_theta_min     3.97
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     27.48
_diffrn_measured_fraction_theta_full     27.49
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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     2410
_reflns_number_gt     1444
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0982
_refine_ls_R_factor_gt     0.0613
_refine_ls_wR_factor_all     ?
_refine_ls_wR_factor_ref     0.2565
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     2410
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.15P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.243
_refine_diff_density_min     -0.221
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.063(14)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
    'N' 'N' 0.0061 0.0033
                         '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     'RAPID-AUTO (Rigaku 2004)'
_computing_cell_refinement     'RAPID-AUTO'
_computing_data_reduction     'RAPID-AUTO'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_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
    O O1 0.25512(14) 0.1587(4) 0.82721(12) 0.0768(6) Uani d . 1 . .
    O O2 0.46364(16) 0.6933(5) 0.89829(16) 0.0964(8) Uani d . 1 . .
    N N1 0.19230(16) 0.2155(5) 0.89941(16) 0.0764(7) Uani d . 1 . .
    C C1 0.1178(3) 0.6683(8) 1.0260(2) 0.1056(12) Uani d . 1 . .
    H H1 0.1011 0.7383 0.9678 0.127 Uiso calc R 1 . .
    C C2 0.0734(3) 0.7530(11) 1.1046(3) 0.1268(16) Uani d . 1 . .
    H H2 0.0286 0.8828 1.0989 0.152 Uiso calc R 1 . .
    C C3 0.0946(3) 0.6488(8) 1.1894(2) 0.0954(11) Uani d . 1 . .
    H H3 0.0626 0.7004 1.2417 0.114 Uiso calc R 1 . .
    C C4 0.1624(4) 0.4698(8) 1.1971(2) 0.1256(16) Uani d . 1 . .
    H H4 0.1793 0.4015 1.2556 0.151 Uiso calc R 1 . .
    C C5 0.2073(4) 0.3863(7) 1.1188(2) 0.1178(15) Uani d . 1 . .
    H H5 0.2535 0.2602 1.1250 0.141 Uiso calc R 1 . .
    C C6 0.18481(17) 0.4861(5) 1.03262(16) 0.0601(6) Uani d . 1 . .
    C C7 0.23385(16) 0.3934(5) 0.94913(15) 0.0572(6) Uani d . 1 . .
    C C8 0.32306(15) 0.4644(4) 0.91255(14) 0.0536(6) Uani d . 1 . .
    C C9 0.39362(17) 0.6557(5) 0.94341(16) 0.0607(6) Uani d . 1 . .
    C C10 0.3788(2) 0.8049(6) 1.0298(2) 0.0759(8) Uani d . 1 . .
    H H10C 0.4307 0.9216 1.0404 0.114 Uiso calc R 1 . .
    H H10B 0.3759 0.6913 1.0823 0.114 Uiso calc R 1 . .
    H H10A 0.3204 0.8984 1.0226 0.114 Uiso calc R 1 . .
    C C11 0.33123(17) 0.3083(5) 0.83683(15) 0.0596(6) Uani d . 1 . .
    C C12 0.4041(2) 0.2697(6) 0.76707(18) 0.0747(8) Uani d . 1 . .
    H H12C 0.3831 0.1407 0.7232 0.112 Uiso calc R 1 . .
    H H12B 0.4626 0.2171 0.7984 0.112 Uiso calc R 1 . .
    H H12A 0.4141 0.4264 0.7342 0.112 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 0.0791(12) 0.0874(13) 0.0643(11) -0.0131(10) 0.0068(9) -0.0224(9)
    O2 0.0895(15) 0.1154(17) 0.0872(14) -0.0362(12) 0.0347(12) -0.0201(12)
    N1 0.0676(13) 0.0920(16) 0.0700(14) -0.0163(12) 0.0102(11) -0.0163(12)
    C1 0.097(2) 0.149(3) 0.0723(18) 0.047(2) 0.0205(16) 0.013(2)
    C2 0.100(3) 0.185(4) 0.098(3) 0.049(3) 0.031(2) -0.010(3)
    C3 0.093(2) 0.114(3) 0.083(2) -0.023(2) 0.0432(17) -0.0238(18)
    C4 0.200(5) 0.117(3) 0.0626(18) 0.023(3) 0.041(2) 0.0083(19)
    C5 0.189(4) 0.109(3) 0.0579(16) 0.054(3) 0.031(2) 0.0109(17)
    C6 0.0593(13) 0.0657(13) 0.0562(12) -0.0088(11) 0.0110(9) -0.0029(10)
    C7 0.0600(13) 0.0618(13) 0.0495(11) -0.0031(10) 0.0014(9) -0.0015(10)
    C8 0.0594(12) 0.0574(12) 0.0443(10) -0.0003(9) 0.0039(8) 0.0016(9)
    C9 0.0608(13) 0.0638(13) 0.0580(13) -0.0030(10) 0.0079(10) 0.0016(10)
    C10 0.0687(16) 0.0788(17) 0.0808(17) -0.0105(13) 0.0092(13) -0.0204(14)
    C11 0.0646(14) 0.0658(13) 0.0481(11) 0.0042(11) 0.0014(10) -0.0008(10)
    C12 0.0772(17) 0.0907(19) 0.0568(13) 0.0156(14) 0.0102(12) -0.0067(13)
_geom_special_details     ?
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 C11 . 1.331(3) ?
    O1 N1 . 1.421(3) ?
    O2 C9 . 1.219(3) ?
    N1 C7 . 1.297(3) ?
    C1 C6 . 1.344(4) ?
    C1 C2 . 1.383(5) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.350(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.341(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.381(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.362(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.487(3) ?
    C7 C8 . 1.432(3) ?
    C8 C11 . 1.366(3) ?
    C8 C9 . 1.467(3) ?
    C9 C10 . 1.484(4) ?
    C10 H10C . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10A . 0.9600 ?
    C11 C12 . 1.477(3) ?
    C12 H12C . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12A . 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
    C11 O1 N1 . . 109.08(17) ?
    C7 N1 O1 . . 105.53(19) ?
    C6 C1 C2 . . 121.0(3) ?
    C6 C1 H1 . . 119.5 ?
    C2 C1 H1 . . 119.5 ?
    C3 C2 C1 . . 120.5(4) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C4 C3 C2 . . 119.1(3) ?
    C4 C3 H3 . . 120.5 ?
    C2 C3 H3 . . 120.5 ?
    C3 C4 C5 . . 120.4(4) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C6 C5 C4 . . 120.9(4) ?
    C6 C5 H5 . . 119.5 ?
    C4 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 118.1(3) ?
    C1 C6 C7 . . 121.8(2) ?
    C5 C6 C7 . . 120.1(3) ?
    N1 C7 C8 . . 111.7(2) ?
    N1 C7 C6 . . 117.4(2) ?
    C8 C7 C6 . . 130.9(2) ?
    C11 C8 C7 . . 103.9(2) ?
    C11 C8 C9 . . 124.6(2) ?
    C7 C8 C9 . . 131.5(2) ?
    O2 C9 C8 . . 120.4(2) ?
    O2 C9 C10 . . 120.1(2) ?
    C8 C9 C10 . . 119.5(2) ?
    C9 C10 H10C . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10C C10 H10B . . 109.5 ?
    C9 C10 H10A . . 109.5 ?
    H10C C10 H10A . . 109.5 ?
    H10B C10 H10A . . 109.5 ?
    O1 C11 C8 . . 109.8(2) ?
    O1 C11 C12 . . 115.5(2) ?
    C8 C11 C12 . . 134.6(2) ?
    C11 C12 H12C . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12C C12 H12B . . 109.5 ?
    C11 C12 H12A . . 109.5 ?
    H12C C12 H12A . . 109.5 ?
    H12B C12 H12A . . 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
    C11 O1 N1 C7 . . . . -0.6(3) ?
    C6 C1 C2 C3 . . . . -1.9(7) ?
    C1 C2 C3 C4 . . . . 2.9(7) ?
    C2 C3 C4 C5 . . . . -2.5(7) ?
    C3 C4 C5 C6 . . . . 1.0(8) ?
    C2 C1 C6 C5 . . . . 0.4(6) ?
    C2 C1 C6 C7 . . . . -179.6(4) ?
    C4 C5 C6 C1 . . . . 0.1(7) ?
    C4 C5 C6 C7 . . . . -179.9(4) ?
    O1 N1 C7 C8 . . . . 0.9(3) ?
    O1 N1 C7 C6 . . . . -178.2(2) ?
    C1 C6 C7 N1 . . . . -85.0(4) ?
    C5 C6 C7 N1 . . . . 95.1(4) ?
    C1 C6 C7 C8 . . . . 96.2(4) ?
    C5 C6 C7 C8 . . . . -83.8(4) ?
    N1 C7 C8 C11 . . . . -0.9(3) ?
    C6 C7 C8 C11 . . . . 178.0(2) ?
    N1 C7 C8 C9 . . . . 179.0(2) ?
    C6 C7 C8 C9 . . . . -2.1(4) ?
    C11 C8 C9 O2 . . . . 3.5(4) ?
    C7 C8 C9 O2 . . . . -176.3(3) ?
    C11 C8 C9 C10 . . . . -176.9(2) ?
    C7 C8 C9 C10 . . . . 3.3(4) ?
    N1 O1 C11 C8 . . . . 0.1(3) ?
    N1 O1 C11 C12 . . . . 179.3(2) ?
    C7 C8 C11 O1 . . . . 0.4(3) ?
    C9 C8 C11 O1 . . . . -179.4(2) ?
    C7 C8 C11 C12 . . . . -178.6(3) ?
    C9 C8 C11 C12 . . . . 1.5(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    ? ? ? ? ? ? ? ? ? ? ?
