##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2006-10-17
_journal_date_accepted     2006-10-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o5280
_journal_page_last     o5281
_journal_paper_category     EO
_journal_coeditor_code     DN2079
_publ_contact_author_name     ' Wang, Hai-bo'
_publ_contact_author_address
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     wanghaibo@njut.edu.cn
_publ_contact_author_fax     '86 25  83369345'
_publ_contact_author_phone     '86 25 83587440'
_publ_section_title
;
2-{2-[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy}-
N-(2,6-dimethylphenyl)acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Ding, Wei-Lin'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Xing, Zhi-Tao'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Liu, Zhi-Qian'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Wang, Pin-Liang'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Wang, Hai-Bo'
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-{2-[3-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy}-
N-(2,6-dimethylphenyl)acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H20 Cl N3 O3'
_chemical_formula_sum     'C24 H20 Cl N3 O3'
_chemical_formula_iupac     'C24 H20 Cl N3 O3'
_chemical_formula_weight     433.88
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.9110(18)
_cell_length_b     10.612(2)
_cell_length_c     12.491(3)
_cell_angle_alpha     94.55(3)
_cell_angle_beta     92.09(3)
_cell_angle_gamma     114.63(3)
_cell_volume     1067.2(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     12
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.350
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     452
_exptl_absorpt_coefficient_mu     0.210
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9196
_exptl_absorpt_correction_T_max     0.9601
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4169
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0541
_diffrn_reflns_theta_min     1.64
_diffrn_reflns_theta_max     25.96
_diffrn_reflns_theta_full     25.96
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     2
_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     4168
_reflns_number_gt     2217
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1240
_refine_ls_R_factor_gt     0.0647
_refine_ls_wR_factor_gt     0.1536
_refine_ls_wR_factor_ref     0.1787
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     4169
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0739P)²+0.0627P] 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     0.412
_refine_diff_density_min     -0.443
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1996)'
_computing_publication_material     'PLATON (Spek, 2003)'
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
    Cl Cl 0.31124(15) 0.01107(14) 0.45634(10) 0.1145(5) Uani d . 1 . .
    O O1 0.1378(3) -0.1414(2) 0.1286(2) 0.0793(7) Uani d . 1 . .
    O O2 0.2266(3) 0.1884(2) -0.04103(17) 0.0633(6) Uani d . 1 . .
    O O3 0.3293(3) 0.5489(2) -0.00480(18) 0.0689(7) Uani d . 1 . .
    N N1 0.0970(4) -0.1142(3) 0.2333(3) 0.0831(9) Uani d . 1 . .
    N N2 0.1925(3) 0.0809(3) 0.1498(2) 0.0604(7) Uani d . 1 . .
    N N3 0.2700(3) 0.3836(2) 0.1122(2) 0.0557(7) Uani d . 1 . .
    H H3 0.2386 0.2960 0.1169 0.067 Uiso calc R 1 . .
    C C1 0.0148(6) 0.2605(5) 0.4120(5) 0.1078(16) Uani d . 1 . .
    H H1 -0.0426 0.3154 0.4041 0.129 Uiso calc R 1 . .
    C C2 0.0859(7) 0.2568(6) 0.5122(5) 0.1181(19) Uani d . 1 . .
    H H2 0.0742 0.3089 0.5721 0.142 Uiso calc R 1 . .
    C C3 0.1726(6) 0.1776(6) 0.5242(4) 0.1099(17) Uani d . 1 . .
    H H3A 0.2197 0.1772 0.5917 0.132 Uiso calc R 1 . .
    C C4 0.1902(5) 0.0997(4) 0.4378(4) 0.0853(12) Uani d . 1 . .
    C C5 0.1179(4) 0.0982(4) 0.3363(3) 0.0675(9) Uani d . 1 . .
    C C6 0.0319(5) 0.1806(4) 0.3247(4) 0.0837(11) Uani d . 1 . .
    H H6 -0.0146 0.1818 0.2571 0.100 Uiso calc R 1 . .
    C C7 0.1351(4) 0.0181(4) 0.2407(3) 0.0634(9) Uani d . 1 . .
    C C8 0.1933(4) -0.0201(3) 0.0840(3) 0.0578(8) Uani d . 1 . .
    C C9 0.2543(4) -0.0186(3) -0.0220(3) 0.0599(9) Uani d . 1 . .
    C C10 0.2985(5) -0.1234(4) -0.0622(3) 0.0769(11) Uani d . 1 . .
    H H10 0.2796 -0.1995 -0.0238 0.092 Uiso calc R 1 . .
    C C11 0.3701(5) -0.1147(5) -0.1585(4) 0.0951(14) Uani d . 1 . .
    H H11 0.3981 -0.1856 -0.1857 0.114 Uiso calc R 1 . .
    C C12 0.4003(5) -0.0011(5) -0.2149(4) 0.0930(13) Uani d . 1 . .
    H H12 0.4521 0.0056 -0.2788 0.112 Uiso calc R 1 . .
    C C13 0.3551(5) 0.1023(4) -0.1779(3) 0.0764(10) Uani d . 1 . .
    H H13 0.3745 0.1776 -0.2173 0.092 Uiso calc R 1 . .
    C C14 0.2808(4) 0.0944(3) -0.0823(3) 0.0606(8) Uani d . 1 . .
    C C15 0.2840(4) 0.3237(3) -0.0770(2) 0.0598(8) Uani d . 1 . .
    H H15A 0.2085 0.3232 -0.1351 0.072 Uiso calc R 1 . .
    H H15B 0.3921 0.3486 -0.1043 0.072 Uiso calc R 1 . .
    C C16 0.2951(4) 0.4289(3) 0.0139(3) 0.0558(8) Uani d . 1 . .
    C C17 0.2924(4) 0.4721(3) 0.2088(2) 0.0521(8) Uani d . 1 . .
    C C18 0.1901(4) 0.5407(3) 0.2254(3) 0.0623(9) Uani d . 1 . .
    C C19 0.2195(5) 0.6293(4) 0.3188(3) 0.0768(11) Uani d . 1 . .
    H H19 0.1546 0.6781 0.3302 0.092 Uiso calc R 1 . .
    C C20 0.3415(6) 0.6459(4) 0.3939(3) 0.0859(12) Uani d . 1 . .
    H H20 0.3603 0.7067 0.4559 0.103 Uiso calc R 1 . .
    C C21 0.4382(5) 0.5739(4) 0.3795(3) 0.0744(10) Uani d . 1 . .
    H H21 0.5191 0.5843 0.4329 0.089 Uiso calc R 1 . .
    C C22 0.4164(4) 0.4863(3) 0.2863(3) 0.0582(8) Uani d . 1 . .
    C C23 0.0471(5) 0.5158(4) 0.1469(3) 0.0817(11) Uani d . 1 . .
    H H23A -0.0298 0.5440 0.1818 0.123 Uiso calc R 1 . .
    H H23B -0.0073 0.4184 0.1216 0.123 Uiso calc R 1 . .
    H H23C 0.0866 0.5689 0.0870 0.123 Uiso calc R 1 . .
    C C24 0.5219(4) 0.4077(4) 0.2716(3) 0.0748(10) Uani d . 1 . .
    H H24A 0.6139 0.4449 0.3250 0.112 Uiso calc R 1 . .
    H H24B 0.5622 0.4169 0.2011 0.112 Uiso calc R 1 . .
    H H24C 0.4571 0.3110 0.2792 0.112 Uiso calc R 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
    Cl C4 . 1.721(5) ?
    O1 C8 . 1.347(3) ?
    O1 N1 . 1.410(4) ?
    O2 C14 . 1.353(4) ?
    O2 C15 . 1.425(3) ?
    O3 C16 . 1.224(3) ?
    N1 C7 . 1.295(4) ?
    N2 C8 . 1.300(4) ?
    N2 C7 . 1.369(4) ?
    N3 C16 . 1.347(4) ?
    N3 C17 . 1.422(4) ?
    N3 H3 . 0.8600 ?
    C1 C6 . 1.380(6) ?
    C1 C2 . 1.393(7) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.370(7) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.360(6) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.398(5) ?
    C5 C6 . 1.394(5) ?
    C5 C7 . 1.461(5) ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.448(5) ?
    C9 C10 . 1.392(4) ?
    C9 C14 . 1.408(5) ?
    C10 C11 . 1.374(6) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.379(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.371(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.378(5) ?
    C13 H13 . 0.9300 ?
    C15 C16 . 1.498(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C17 C22 . 1.394(4) ?
    C17 C18 . 1.395(4) ?
    C18 C19 . 1.384(5) ?
    C18 C23 . 1.497(5) ?
    C19 C20 . 1.354(5) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.377(5) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.384(5) ?
    C21 H21 . 0.9300 ?
    C22 C24 . 1.503(4) ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 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
    C8 O1 N1 . . 107.0(2) ?
    C14 O2 C15 . . 120.9(3) ?
    C7 N1 O1 . . 103.0(3) ?
    C8 N2 C7 . . 103.4(3) ?
    C16 N3 C17 . . 123.9(2) ?
    C16 N3 H3 . . 118.0 ?
    C17 N3 H3 . . 118.0 ?
    C6 C1 C2 . . 118.3(5) ?
    C6 C1 H1 . . 120.9 ?
    C2 C1 H1 . . 120.9 ?
    C3 C2 C1 . . 121.2(5) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C4 C3 C2 . . 120.5(5) ?
    C4 C3 H3A . . 119.8 ?
    C2 C3 H3A . . 119.8 ?
    C3 C4 C5 . . 120.1(5) ?
    C3 C4 Cl . . 118.2(4) ?
    C5 C4 Cl . . 121.6(4) ?
    C6 C5 C4 . . 119.0(4) ?
    C6 C5 C7 . . 118.6(4) ?
    C4 C5 C7 . . 122.4(4) ?
    C1 C6 C5 . . 120.9(5) ?
    C1 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    N1 C7 N2 . . 114.8(3) ?
    N1 C7 C5 . . 124.4(3) ?
    N2 C7 C5 . . 120.8(3) ?
    N2 C8 O1 . . 111.8(3) ?
    N2 C8 C9 . . 130.5(3) ?
    O1 C8 C9 . . 117.6(3) ?
    C10 C9 C14 . . 119.1(3) ?
    C10 C9 C8 . . 120.5(3) ?
    C14 C9 C8 . . 120.2(3) ?
    C11 C10 C9 . . 120.1(4) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C10 C11 C12 . . 120.0(4) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 120.9(4) ?
    C13 C12 H12 . . 119.6 ?
    C11 C12 H12 . . 119.6 ?
    C12 C13 C14 . . 120.0(4) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    O2 C14 C13 . . 124.4(3) ?
    O2 C14 C9 . . 115.8(3) ?
    C13 C14 C9 . . 119.8(3) ?
    O2 C15 C16 . . 110.2(2) ?
    O2 C15 H15A . . 109.6 ?
    C16 C15 H15A . . 109.6 ?
    O2 C15 H15B . . 109.6 ?
    C16 C15 H15B . . 109.6 ?
    H15A C15 H15B . . 108.1 ?
    O3 C16 N3 . . 124.6(3) ?
    O3 C16 C15 . . 119.0(3) ?
    N3 C16 C15 . . 116.5(3) ?
    C22 C17 C18 . . 121.2(3) ?
    C22 C17 N3 . . 118.5(3) ?
    C18 C17 N3 . . 120.3(3) ?
    C19 C18 C17 . . 118.5(3) ?
    C19 C18 C23 . . 120.0(3) ?
    C17 C18 C23 . . 121.5(3) ?
    C20 C19 C18 . . 120.7(4) ?
    C20 C19 H19 . . 119.6 ?
    C18 C19 H19 . . 119.6 ?
    C19 C20 C21 . . 120.8(4) ?
    C19 C20 H20 . . 119.6 ?
    C21 C20 H20 . . 119.6 ?
    C20 C21 C22 . . 120.8(4) ?
    C20 C21 H21 . . 119.6 ?
    C22 C21 H21 . . 119.6 ?
    C21 C22 C17 . . 117.9(3) ?
    C21 C22 C24 . . 120.4(3) ?
    C17 C22 C24 . . 121.7(3) ?
    C18 C23 H23A . . 109.5 ?
    C18 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C18 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C22 C24 H24A . . 109.5 ?
    C22 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C22 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
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
    N3 H3 N2 . 0.86 2.22 3.072(3) 170.4
    N3 H3 O2 . 0.86 2.18 2.599(3) 110.1
    C15 H15B O3 2_665 0.97 2.54 3.223(4) 127.1
