##############################################################################
###                                                                        ###
###        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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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-11-11
_journal_date_accepted     2005-12-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o374
_journal_page_last     o375
_journal_paper_category     EO
_journal_coeditor_code     CI6710
_publ_contact_author_name     ' Jun-Biao Chang'
_publ_contact_author_address
;Department of Chemistry, University of Science and Technology of China
Hefei 230026, People's Republic of China
;
_publ_contact_author_email     jbchang@public2.zz.ha.cn
_publ_contact_author_fax     '86 371 6572 7239'
_publ_contact_author_phone     '86 371 6551 1785'
_publ_section_title
;
5-(1H-Indol-3-yl)-3-(4-methylphenyl)-4,5-dihydroisoxazoline
;
loop_
    _publ_author_name
    _publ_author_address
    'Xiaohe Guo'
;
Department of Chemistry
University of Science and Technology of China
Hefei 230026
People's Republic of China
;
    'Xiouxiang Qi'
;
Lanzhou Institute of Chemical Physics
Chinese Academy of Sciences
Lanzhou 730000
People's Republic of China
;
    'Junbiao Chang'
;
Department of Chemistry
University of Science and Technology of China
Hefei 230026
People's Republic of China
;
data_I
_chemical_name_systematic
;
5-(1H-Indol-3-yl)-3-(4-methylphenyl)-4,5-dihydroisoxazoline
;
_chemical_name_common     3-(4'-methyl)-phenyl-5-(3'-indolyl)-isoxazoline
_chemical_formula_moiety     'C18 H16 N2 O'
_chemical_formula_sum     'C18 H16 N2 O'
_chemical_formula_iupac     'C18 H16 N2 O'
_chemical_formula_weight     276.33
_chemical_melting_point     441
_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     8.1881(19)
_cell_length_b     12.713(3)
_cell_length_c     14.239(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1482.3(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1772
_cell_measurement_theta_min     2.87
_cell_measurement_theta_max     21.23
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     purple
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.238
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9680
_exptl_absorpt_correction_T_max     0.9907
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8368
_diffrn_reflns_av_R_equivalents     0.0500
_diffrn_reflns_av_sigmaI/netI     0.0394
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     26.41
_diffrn_reflns_theta_full     26.41
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_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 > 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     1747
_reflns_number_gt     1120
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0808
_refine_ls_R_factor_gt     0.0390
_refine_ls_wR_factor_gt     0.0764
_refine_ls_wR_factor_ref     0.0926
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     1747
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0374P)²+0.1511P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.112
_refine_diff_density_min     -0.126
_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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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
    O1 1.0214(3) -0.03619(14) 0.58725(13) 0.0585(6) Uani d . 1 . . O
    N1 0.7346(4) -0.2791(2) 0.4315(2) 0.0720(9) Uani d . 1 . . N
    H1A 0.686(6) -0.335(3) 0.424(3) 0.125(17) Uiso d . 1 . . H
    N2 1.0613(3) 0.06924(18) 0.61107(15) 0.0537(6) Uani d . 1 . . N
    C1 0.8258(4) -0.1266(2) 0.4900(2) 0.0512(7) Uani d . 1 . . C
    C2 0.8890(3) -0.1382(2) 0.39596(19) 0.0506(7) Uani d . 1 . . C
    C3 0.9899(4) -0.0790(3) 0.3374(2) 0.0676(9) Uani d . 1 . . C
    H3 1.0326 -0.0151 0.3577 0.081 Uiso calc R 1 . . H
    C4 1.0255(5) -0.1167(3) 0.2486(2) 0.0878(11) Uani d . 1 . . C
    H4 1.0924 -0.0774 0.2092 0.105 Uiso calc R 1 . . H
    C5 0.9634(5) -0.2120(4) 0.2172(3) 0.0971(13) Uani d . 1 . . C
    H5 0.9896 -0.2352 0.1571 0.117 Uiso calc R 1 . . H
    C6 0.8643(5) -0.2726(3) 0.2727(3) 0.0831(11) Uani d . 1 . . C
    H6 0.8230 -0.3366 0.2517 0.100 Uiso calc R 1 . . H
    C7 0.8282(4) -0.2347(2) 0.3618(2) 0.0603(9) Uani d . 1 . . C
    C8 0.7342(4) -0.2139(2) 0.5070(3) 0.0670(9) Uani d . 1 . . C
    H8 0.6787 -0.2270 0.5628 0.080 Uiso calc R 1 . . H
    C9 0.8496(4) -0.0396(2) 0.5576(2) 0.0573(8) Uani d . 1 . . C
    H9 0.7820 -0.0536 0.6130 0.069 Uiso calc R 1 . . H
    C10 0.8191(4) 0.0732(2) 0.5261(2) 0.0588(8) Uani d . 1 . . C
    H10A 0.8329 0.0812 0.4588 0.071 Uiso calc R 1 . . H
    H10B 0.7110 0.0973 0.5439 0.071 Uiso calc R 1 . . H
    C11 0.9497(4) 0.1296(2) 0.57947(17) 0.0465(6) Uani d . 1 . . C
    C12 0.9562(4) 0.2435(2) 0.59429(17) 0.0459(7) Uani d . 1 . . C
    C13 1.0595(4) 0.2882(2) 0.66125(19) 0.0539(7) Uani d . 1 . . C
    H13 1.1280 0.2452 0.6965 0.065 Uiso calc R 1 . . H
    C14 1.0607(4) 0.3958(2) 0.67571(19) 0.0579(8) Uani d . 1 . . C
    H14 1.1309 0.4240 0.7204 0.070 Uiso calc R 1 . . H
    C15 0.9599(4) 0.4624(2) 0.62517(19) 0.0519(7) Uani d . 1 . . C
    C16 0.8611(4) 0.4184(2) 0.5577(2) 0.0574(8) Uani d . 1 . . C
    H16 0.7948 0.4617 0.5214 0.069 Uiso calc R 1 . . H
    C17 0.8587(4) 0.3108(2) 0.54274(19) 0.0533(7) Uani d . 1 . . C
    H17 0.7899 0.2832 0.4970 0.064 Uiso calc R 1 . . H
    C18 0.9587(4) 0.5789(2) 0.6439(2) 0.0702(9) Uani d . 1 . . C
    H18A 0.9517 0.6162 0.5854 0.105 Uiso calc R 1 . . H
    H18B 1.0574 0.5984 0.6758 0.105 Uiso calc R 1 . . H
    H18C 0.8663 0.5963 0.6823 0.105 Uiso calc R 1 . . H
_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 N2 . 1.421(3) ?
    O1 C9 . 1.469(4) ?
    N1 C8 . 1.358(4) ?
    N1 C7 . 1.375(4) ?
    N1 H1A . 0.82(4) ?
    N2 C11 . 1.275(3) ?
    C1 C8 . 1.361(4) ?
    C1 C2 . 1.443(4) ?
    C1 C9 . 1.479(4) ?
    C2 C3 . 1.395(4) ?
    C2 C7 . 1.410(4) ?
    C3 C4 . 1.383(5) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.388(5) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.370(5) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.389(4) ?
    C6 H6 . 0.93 ?
    C8 H8 . 0.93 ?
    C9 C10 . 1.524(4) ?
    C9 H9 . 0.98 ?
    C10 C11 . 1.495(4) ?
    C10 H10A . 0.97 ?
    C10 H10B . 0.97 ?
    C11 C12 . 1.464(3) ?
    C12 C17 . 1.382(3) ?
    C12 C13 . 1.395(4) ?
    C13 C14 . 1.383(4) ?
    C13 H13 . 0.93 ?
    C14 C15 . 1.384(4) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.375(4) ?
    C15 C18 . 1.505(4) ?
    C16 C17 . 1.385(4) ?
    C16 H16 . 0.93 ?
    C17 H17 . 0.93 ?
    C18 H18A . 0.96 ?
    C18 H18B . 0.96 ?
    C18 H18C . 0.96 ?
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
    N2 O1 C9 . . 108.48(19) ?
    C8 N1 C7 . . 108.7(3) ?
    C8 N1 H1A . . 129(3) ?
    C7 N1 H1A . . 122(3) ?
    C11 N2 O1 . . 108.6(2) ?
    C8 C1 C2 . . 106.2(3) ?
    C8 C1 C9 . . 124.5(3) ?
    C2 C1 C9 . . 129.3(3) ?
    C3 C2 C7 . . 118.2(3) ?
    C3 C2 C1 . . 135.4(3) ?
    C7 C2 C1 . . 106.4(3) ?
    C4 C3 C2 . . 119.0(3) ?
    C4 C3 H3 . . 120.5 ?
    C2 C3 H3 . . 120.5 ?
    C3 C4 C5 . . 121.3(3) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C6 C5 C4 . . 121.5(4) ?
    C6 C5 H5 . . 119.3 ?
    C4 C5 H5 . . 119.3 ?
    C5 C6 C7 . . 117.2(3) ?
    C5 C6 H6 . . 121.4 ?
    C7 C6 H6 . . 121.4 ?
    N1 C7 C6 . . 129.4(3) ?
    N1 C7 C2 . . 107.8(3) ?
    C6 C7 C2 . . 122.8(3) ?
    N1 C8 C1 . . 110.9(3) ?
    N1 C8 H8 . . 124.6 ?
    C1 C8 H8 . . 124.6 ?
    O1 C9 C1 . . 109.6(2) ?
    O1 C9 C10 . . 102.3(2) ?
    C1 C9 C10 . . 119.4(2) ?
    O1 C9 H9 . . 108.3 ?
    C1 C9 H9 . . 108.3 ?
    C10 C9 H9 . . 108.3 ?
    C11 C10 C9 . . 100.6(2) ?
    C11 C10 H10A . . 111.7 ?
    C9 C10 H10A . . 111.7 ?
    C11 C10 H10B . . 111.7 ?
    C9 C10 H10B . . 111.7 ?
    H10A C10 H10B . . 109.4 ?
    N2 C11 C12 . . 121.2(3) ?
    N2 C11 C10 . . 113.8(2) ?
    C12 C11 C10 . . 125.0(3) ?
    C17 C12 C13 . . 117.5(2) ?
    C17 C12 C11 . . 121.0(2) ?
    C13 C12 C11 . . 121.5(2) ?
    C14 C13 C12 . . 120.6(3) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 121.5(3) ?
    C13 C14 H14 . . 119.2 ?
    C15 C14 H14 . . 119.2 ?
    C16 C15 C14 . . 117.8(3) ?
    C16 C15 C18 . . 121.3(3) ?
    C14 C15 C18 . . 120.9(3) ?
    C15 C16 C17 . . 121.1(3) ?
    C15 C16 H16 . . 119.4 ?
    C17 C16 H16 . . 119.4 ?
    C12 C17 C16 . . 121.5(3) ?
    C12 C17 H17 . . 119.3 ?
    C16 C17 H17 . . 119.3 ?
    C15 C18 H18A . . 109.5 ?
    C15 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C15 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 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
    C9 O1 N2 C11 . . . . -14.5(3) ?
    C8 C1 C2 C3 . . . . -179.3(3) ?
    C9 C1 C2 C3 . . . . 1.1(6) ?
    C8 C1 C2 C7 . . . . 0.3(3) ?
    C9 C1 C2 C7 . . . . -179.3(3) ?
    C7 C2 C3 C4 . . . . 0.3(4) ?
    C1 C2 C3 C4 . . . . 179.8(3) ?
    C2 C3 C4 C5 . . . . -0.2(5) ?
    C3 C4 C5 C6 . . . . 0.0(6) ?
    C4 C5 C6 C7 . . . . 0.2(5) ?
    C8 N1 C7 C6 . . . . 179.7(3) ?
    C8 N1 C7 C2 . . . . 0.4(4) ?
    C5 C6 C7 N1 . . . . -179.3(3) ?
    C5 C6 C7 C2 . . . . -0.1(5) ?
    C3 C2 C7 N1 . . . . 179.2(3) ?
    C1 C2 C7 N1 . . . . -0.4(3) ?
    C3 C2 C7 C6 . . . . -0.1(4) ?
    C1 C2 C7 C6 . . . . -179.8(3) ?
    C7 N1 C8 C1 . . . . -0.2(4) ?
    C2 C1 C8 N1 . . . . 0.0(4) ?
    C9 C1 C8 N1 . . . . 179.6(3) ?
    N2 O1 C9 C1 . . . . 151.5(2) ?
    N2 O1 C9 C10 . . . . 23.8(3) ?
    C8 C1 C9 O1 . . . . 113.6(3) ?
    C2 C1 C9 O1 . . . . -66.9(4) ?
    C8 C1 C9 C10 . . . . -128.9(3) ?
    C2 C1 C9 C10 . . . . 50.6(4) ?
    O1 C9 C10 C11 . . . . -22.9(3) ?
    C1 C9 C10 C11 . . . . -144.1(3) ?
    O1 N2 C11 C12 . . . . 179.2(2) ?
    O1 N2 C11 C10 . . . . -2.0(3) ?
    C9 C10 C11 N2 . . . . 16.5(3) ?
    C9 C10 C11 C12 . . . . -164.8(2) ?
    N2 C11 C12 C17 . . . . 164.8(3) ?
    C10 C11 C12 C17 . . . . -13.8(4) ?
    N2 C11 C12 C13 . . . . -15.8(4) ?
    C10 C11 C12 C13 . . . . 165.5(3) ?
    C17 C12 C13 C14 . . . . 1.0(4) ?
    C11 C12 C13 C14 . . . . -178.4(3) ?
    C12 C13 C14 C15 . . . . 0.4(4) ?
    C13 C14 C15 C16 . . . . -1.9(4) ?
    C13 C14 C15 C18 . . . . 178.0(3) ?
    C14 C15 C16 C17 . . . . 2.0(4) ?
    C18 C15 C16 C17 . . . . -177.9(3) ?
    C13 C12 C17 C16 . . . . -0.9(4) ?
    C11 C12 C17 C16 . . . . 178.5(3) ?
    C15 C16 C17 C12 . . . . -0.6(5) ?
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
    N1 H1A O1 4_446 0.82(4) 2.13(4) 2.937(4) 170(5)
