##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2016/4'
_database_code_depnum_ccdc_archive     'CCDC 1534636'
_chemical_name_systematic
;
Ethyl 5-phenylisoxazole-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H11 N O3'
_chemical_formula_sum     'C12 H11 N O3'
_chemical_formula_iupac     'C12 H11 N O3'
_chemical_formula_weight     217.22
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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     5.4447(7)
_cell_length_b     17.180(2)
_cell_length_c     11.7603(19)
_cell_angle_alpha     90
_cell_angle_beta     94.508(5)
_cell_angle_gamma     90
_cell_volume     1096.6(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5392
_cell_measurement_theta_min     2.37
_cell_measurement_theta_max     30.53
_cell_measurement_temperature     100(2)
_exptl_crystal_description     blocks
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.316
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14119
_diffrn_reflns_av_R_equivalents     0.0749
_diffrn_reflns_theta_min     2.371
_diffrn_reflns_theta_max     28.693
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_refine_special_details     ?
_reflns_number_total     2813
_reflns_number_gt     1889
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1108
_refine_ls_R_factor_gt     0.0636
_refine_ls_wR_factor_gt     0.1526
_refine_ls_wR_factor_ref     0.1772
_refine_ls_goodness_of_fit_ref     1.087
_refine_ls_restrained_S_all     1.087
_refine_ls_number_reflns     2813
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1000P)²] 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     0.271
_refine_diff_density_min     -0.303
_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'
    '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
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.1048(2) 0.62026(7) 0.20002(11) 0.0221(4) Uani d 1 . .
    O O3 -0.4360(3) 0.73867(7) 0.01862(12) 0.0230(4) Uani d 1 . .
    O O2 -0.6161(2) 0.62208(7) -0.01700(11) 0.0243(4) Uani d 1 . .
    C C10 -0.4499(3) 0.66119(10) 0.02530(16) 0.0184(4) Uani d 1 . .
    C C6 0.1914(3) 0.48387(10) 0.22525(16) 0.0181(4) Uani d 1 . .
    N N1 -0.0666(3) 0.67215(8) 0.14685(14) 0.0225(4) Uani d 1 . .
    C C4 0.5520(4) 0.44302(11) 0.34137(19) 0.0256(5) Uani d 1 . .
    H H4 0.692513 0.455560 0.387897 0.031 Uiso calc 1 . .
    C C7 0.0322(4) 0.54579(9) 0.17410(16) 0.0174(4) Uani d 1 . .
    C C9 -0.2320(3) 0.62718(10) 0.09196(15) 0.0180(4) Uani d 1 . .
    C C5 0.4000(4) 0.50161(10) 0.29503(17) 0.0234(5) Uani d 1 . .
    H H5 0.438869 0.553372 0.311094 0.028 Uiso calc 1 . .
    C C3 0.4941(4) 0.36559(11) 0.31817(17) 0.0249(5) Uani d 1 . .
    H H3 0.596502 0.326217 0.348598 0.030 Uiso calc 1 . .
    C C1 0.1308(4) 0.40540(10) 0.20262(16) 0.0203(4) Uani d 1 . .
    H H1 -0.010182 0.392615 0.156628 0.024 Uiso calc 1 . .
    C C12 -0.5855(4) 0.86283(11) -0.04174(18) 0.0273(5) Uani d 1 . .
    H H12A -0.579681 0.880375 0.035929 0.041 Uiso calc 1 . .
    H H12B -0.711938 0.890614 -0.086440 0.041 Uiso calc 1 . .
    H H12C -0.429204 0.872225 -0.071751 0.041 Uiso calc 1 . .
    C C8 -0.1780(3) 0.54715(9) 0.10639(16) 0.0185(4) Uani d 1 . .
    H H8 -0.267753 0.504983 0.075862 0.022 Uiso calc 1 . .
    C C11 -0.6410(4) 0.77721(11) -0.04635(18) 0.0243(5) Uani d 1 . .
    H H11A -0.794720 0.766468 -0.012878 0.029 Uiso calc 1 . .
    H H11B -0.654755 0.759053 -0.124690 0.029 Uiso calc 1 . .
    C C2 0.2846(4) 0.34724(10) 0.24996(17) 0.0237(5) Uani d 1 . .
    H H2 0.245566 0.295307 0.235394 0.028 Uiso calc 1 . .
_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 C7 . 1.366(2) ?
    O1 N1 . 1.4018(19) ?
    O3 C10 . 1.336(2) ?
    O3 C11 . 1.461(2) ?
    O2 C10 . 1.203(2) ?
    C10 C9 . 1.489(3) ?
    C6 C5 . 1.382(3) ?
    C6 C1 . 1.408(2) ?
    C6 C7 . 1.471(2) ?
    N1 C9 . 1.317(2) ?
    C4 C3 . 1.389(3) ?
    C4 C5 . 1.387(3) ?
    C4 H4 . 0.9300 ?
    C7 C8 . 1.342(3) ?
    C9 C8 . 1.413(2) ?
    C5 H5 . 0.9300 ?
    C3 C2 . 1.379(3) ?
    C3 H3 . 0.9300 ?
    C1 C2 . 1.391(3) ?
    C1 H1 . 0.9300 ?
    C12 C11 . 1.502(2) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C8 H8 . 0.9300 ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C2 H2 . 0.9300 ?
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
    C7 O1 N1 . . 108.98(13) ?
    C10 O3 C11 . . 115.97(14) ?
    O2 C10 O3 . . 125.19(16) ?
    O2 C10 C9 . . 122.75(16) ?
    O3 C10 C9 . . 112.06(15) ?
    C5 C6 C1 . . 119.53(17) ?
    C5 C6 C7 . . 120.93(16) ?
    C1 C6 C7 . . 119.54(17) ?
    C9 N1 O1 . . 104.55(14) ?
    C3 C4 C5 . . 119.89(19) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 H4 . . 120.1 ?
    O1 C7 C8 . . 109.53(15) ?
    O1 C7 C6 . . 115.78(16) ?
    C8 C7 C6 . . 134.68(16) ?
    C8 C9 N1 . . 112.59(16) ?
    C8 C9 C10 . . 126.49(16) ?
    N1 C9 C10 . . 120.92(15) ?
    C6 C5 C4 . . 120.69(17) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C2 C3 C4 . . 119.87(18) ?
    C2 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    C2 C1 C6 . . 119.14(18) ?
    C2 C1 H1 . . 120.4 ?
    C6 C1 H1 . . 120.4 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C9 C8 C7 . . 104.35(15) ?
    C9 C8 H8 . . 127.8 ?
    C7 C8 H8 . . 127.8 ?
    O3 C11 C12 . . 106.35(15) ?
    O3 C11 H11A . . 110.5 ?
    C12 C11 H11A . . 110.5 ?
    O3 C11 H11B . . 110.5 ?
    C12 C11 H11B . . 110.5 ?
    H11A C11 H11B . . 108.7 ?
    C3 C2 C1 . . 120.87(17) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
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 O3 C10 O2 . . . . -0.4(3) ?
    C11 O3 C10 C9 . . . . 179.40(15) ?
    C7 O1 N1 C9 . . . . -0.10(19) ?
    N1 O1 C7 C8 . . . . 0.15(19) ?
    N1 O1 C7 C6 . . . . -179.04(15) ?
    C5 C6 C7 O1 . . . . 0.1(3) ?
    C1 C6 C7 O1 . . . . -179.73(15) ?
    C5 C6 C7 C8 . . . . -178.8(2) ?
    C1 C6 C7 C8 . . . . 1.3(3) ?
    O1 N1 C9 C8 . . . . 0.0(2) ?
    O1 N1 C9 C10 . . . . 179.04(15) ?
    O2 C10 C9 C8 . . . . 6.0(3) ?
    O3 C10 C9 C8 . . . . -173.78(16) ?
    O2 C10 C9 N1 . . . . -172.86(18) ?
    O3 C10 C9 N1 . . . . 7.3(2) ?
    C1 C6 C5 C4 . . . . 1.1(3) ?
    C7 C6 C5 C4 . . . . -178.82(18) ?
    C3 C4 C5 C6 . . . . -0.4(3) ?
    C5 C4 C3 C2 . . . . -0.6(3) ?
    C5 C6 C1 C2 . . . . -0.9(3) ?
    C7 C6 C1 C2 . . . . 179.02(17) ?
    N1 C9 C8 C7 . . . . 0.1(2) ?
    C10 C9 C8 C7 . . . . -178.89(17) ?
    O1 C7 C8 C9 . . . . -0.13(19) ?
    C6 C7 C8 C9 . . . . 178.9(2) ?
    C10 O3 C11 C12 . . . . 179.89(15) ?
    C4 C3 C2 C1 . . . . 0.8(3) ?
    C6 C1 C2 C3 . . . . 0.0(3) ?
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
    C1 H1 O2 3_465 0.93 2.52 3.447(2) 171
    C8 H8 O2 3_465 0.93 2.36 3.260(2) 163
data_Global
_journal_date_recd_electronic     2017-02-01
_journal_date_accepted     2017-02-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      4
_journal_page_first     531
_journal_page_last     534
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017003127
_journal_coeditor_code     SU5350
_publ_contact_author_name     'Vijay Thiruvenkatam'
_publ_contact_author_address
;
Department of Physics & Bio-Engineering,
IIT Gandhinagar, Palaj Campus, Gandhinagar, Gujarat
;
_publ_contact_author_email     vijay@iitgn.ac.in
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure and Hirshfeld surface analysis of ethyl
5-phenylisoxazole-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shaik, Althaf'
;
Department of Chemistry, IIT Gandhinagar, Gujarat
;
    'Kirubakaran, Sivapriya'
;
Department of Chemistry, IIT Gandhinagar, Gujarat
;
    'Thiruvenkatam, Vijay'
;
Department of Physics & Bio-Engineering, IIT Gandhinagar, Palaj Campus,
Gandhinagar, Gujarat
;
_publ_section_synopsis
;
In the title isoxazole derivative, the phenyl and isoxazole rings are in the
same plane, as indicated by the C---C---C---O torsion angle of 0.1(3)°. The
ester group has an extended conformation and is almost in the same plane with
respect to the isoxazole ring, as indicated by the O---C---C---N torsion angle
of -172.86(18)°.
;
