##############################################################################
###                                                                        ###
###        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.                                        #
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# 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  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-08-17
_journal_date_accepted     2006-09-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4388
_journal_page_last     o4390
_journal_paper_category     EO
_journal_coeditor_code     BI2059
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
    Department of Chemistry,
    The University of Texas,
    One UTSA Circle,
    San Antonio, Texas 78249-0698,
    U.S.A.
;
_publ_contact_author_email     edward.tiekink@utsa.edu
_publ_contact_author_fax     ' 1 210 458 7428 '
_publ_contact_author_phone     ' 1 210 458 5774 '
_publ_section_title
;
1-[5-(3,6-Dichloropyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Song, Qing-Bao'
;
Additional correspondence author, e-mail: qbsong6@163.com
;
;
The State Key Laboratory Breeding Base of
Green Chemistry-Synthesis and Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Zhang, Jie' .
;
The State Key Laboratory Breeding Base of
Green Chemistry-Synthesis and Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Yu Dong' .
;
The State Key Laboratory Breeding Base of
Green Chemistry-Synthesis and Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry
The University of Texas at San Antonio
One UTSA Circle
San Antonio
Texas 78249-0698
USA
;
data_I
_chemical_name_systematic
;
1-[5-(3,6-Dichloropyridin-2-yl)-2,2-dimethyl-1,3,4-oxadiazol-3-yl]ethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 Cl2 N3 O2'
_chemical_formula_sum     'C11 H11 Cl2 N3 O2'
_chemical_formula_iupac     'C11 H11 Cl2 N3 O2'
_chemical_formula_weight     288.13
_chemical_melting_point     ?
_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     11.1149(19)
_cell_length_b     8.1943(13)
_cell_length_c     14.122(2)
_cell_angle_alpha     90
_cell_angle_beta     93.554(3)
_cell_angle_gamma     90
_cell_volume     1283.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5183
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     30.6
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.491
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.503
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.668
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details     ?
_diffrn_ambient_temperature     173(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     'Rigaku AFC12κ/SATURN724 CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     32711
_diffrn_reflns_av_R_equivalents     0.029
_diffrn_reflns_av_sigmaI/netI     0.012
_diffrn_reflns_theta_min     2.3
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_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     2924
_reflns_number_gt     2887
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.042
_refine_ls_R_factor_gt     0.040
_refine_ls_wR_factor_gt     0.123
_refine_ls_wR_factor_ref     0.135
_refine_ls_goodness_of_fit_ref     1.18
_refine_ls_restrained_S_all     1.18
_refine_ls_number_reflns     2924
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0762P)²+0.4744P] 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     0.27
_refine_diff_density_min     -0.35
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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
                              'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction     'CrystalClear'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                       'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_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
    Cl Cl1 0.93462(4) 0.87254(8) -0.10314(4) 0.0523(2) Uani d . 1 . .
    Cl Cl2 0.77170(4) 0.48665(7) 0.24046(3) 0.04466(18) Uani d . 1 . .
    O O1 0.54047(10) 0.80222(15) 0.04455(9) 0.0317(3) Uani d . 1 . .
    O O2 0.22748(11) 0.57282(17) 0.13400(10) 0.0380(3) Uani d . 1 . .
    N N1 0.54303(12) 0.56763(18) 0.12651(10) 0.0278(3) Uani d . 1 . .
    N N2 0.42304(12) 0.61429(17) 0.10955(10) 0.0275(3) Uani d . 1 . .
    N N3 0.77364(13) 0.76615(18) 0.00831(11) 0.0298(3) Uani d . 1 . .
    C C1 0.60406(14) 0.67882(19) 0.08809(11) 0.0258(3) Uani d . 1 . .
    C C2 0.41458(14) 0.7796(2) 0.06637(11) 0.0264(3) Uani d . 1 . .
    C C3 0.33179(15) 0.5243(2) 0.14320(12) 0.0280(3) Uani d . 1 . .
    C C4 0.36809(16) 0.3651(2) 0.18937(12) 0.0319(4) Uani d . 1 . .
    H H4A 0.2958 0.3045 0.2046 0.048 Uiso calc R 1 . .
    H H4B 0.4179 0.3863 0.2477 0.048 Uiso calc R 1 . .
    H H4C 0.4142 0.3005 0.1458 0.048 Uiso calc R 1 . .
    C C5 0.38273(19) 0.9073(2) 0.13736(14) 0.0388(4) Uani d . 1 . .
    H H5A 0.2985 0.8935 0.1526 0.058 Uiso calc R 1 . .
    H H5B 0.3936 1.0161 0.1104 0.058 Uiso calc R 1 . .
    H H5C 0.4353 0.8954 0.1953 0.058 Uiso calc R 1 . .
    C C6 0.33842(15) 0.7869(2) -0.02577(12) 0.0331(4) Uani d . 1 . .
    H H6A 0.2534 0.7722 -0.0131 0.050 Uiso calc R 1 . .
    H H6B 0.3633 0.7001 -0.0681 0.050 Uiso calc R 1 . .
    H H6C 0.3491 0.8932 -0.0560 0.050 Uiso calc R 1 . .
    C C7 0.73568(14) 0.6799(2) 0.08202(11) 0.0261(3) Uani d . 1 . .
    C C8 0.88991(15) 0.7670(2) -0.00442(13) 0.0332(4) Uani d . 1 . .
    C C9 0.97700(16) 0.6893(3) 0.05348(14) 0.0380(4) Uani d . 1 . .
    H H9 1.0600 0.6955 0.0412 0.046 Uiso calc R 1 . .
    C C10 0.93898(16) 0.6032(2) 0.12927(14) 0.0368(4) Uani d . 1 . .
    H H10 0.9957 0.5488 0.1713 0.044 Uiso calc R 1 . .
    C C11 0.81627(15) 0.5962(2) 0.14419(12) 0.0300(3) Uani d . 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
    Cl1 0.0358(3) 0.0712(4) 0.0506(3) -0.0075(2) 0.0071(2) 0.0240(3)
    Cl2 0.0358(3) 0.0605(4) 0.0368(3) -0.0013(2) -0.00417(19) 0.0194(2)
    O1 0.0215(5) 0.0303(6) 0.0433(7) 0.0020(4) 0.0022(5) 0.0093(5)
    O2 0.0234(6) 0.0408(7) 0.0503(8) 0.0004(5) 0.0054(5) 0.0048(6)
    N1 0.0217(6) 0.0295(7) 0.0322(7) 0.0025(5) 0.0009(5) 0.0027(5)
    N2 0.0205(6) 0.0271(7) 0.0348(7) 0.0027(5) 0.0014(5) 0.0050(5)
    N3 0.0245(6) 0.0318(7) 0.0329(7) -0.0001(5) 0.0002(5) 0.0034(6)
    C1 0.0250(7) 0.0250(8) 0.0269(7) 0.0009(6) -0.0012(6) -0.0008(6)
    C2 0.0217(7) 0.0257(8) 0.0319(8) 0.0013(6) 0.0026(6) 0.0019(6)
    C3 0.0251(7) 0.0297(8) 0.0293(7) -0.0010(6) 0.0036(6) -0.0022(6)
    C4 0.0336(8) 0.0289(8) 0.0338(8) -0.0026(6) 0.0064(6) 0.0016(6)
    C5 0.0452(11) 0.0329(9) 0.0389(9) 0.0037(8) 0.0067(8) -0.0045(7)
    C6 0.0296(8) 0.0356(9) 0.0336(8) 0.0011(7) -0.0020(7) 0.0031(7)
    C7 0.0243(7) 0.0269(8) 0.0270(7) -0.0005(6) -0.0004(6) -0.0001(6)
    C8 0.0265(8) 0.0381(9) 0.0350(8) -0.0028(7) 0.0017(6) 0.0054(7)
    C9 0.0222(7) 0.0447(10) 0.0469(10) 0.0002(7) 0.0009(7) 0.0051(8)
    C10 0.0259(8) 0.0416(10) 0.0417(9) 0.0031(7) -0.0066(7) 0.0066(8)
    C11 0.0276(8) 0.0328(9) 0.0293(7) -0.0012(6) -0.0022(6) 0.0020(6)
_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
    Cl1 C8 . 1.7392(18) ?
    Cl2 C11 . 1.7270(18) ?
    O1 C1 . 1.3587(19) y
    O1 C2 . 1.4630(18) y
    O2 C3 . 1.225(2) y
    N1 C1 . 1.277(2) y
    N1 N2 . 1.3938(18) y
    N2 C2 . 1.486(2) y
    N2 C3 . 1.363(2) y
    N3 C7 . 1.347(2) y
    N3 C8 . 1.316(2) y
    C1 C7 . 1.471(2) ?
    C2 C5 . 1.506(2) ?
    C2 C6 . 1.509(2) ?
    C3 C4 . 1.503(2) ?
    C4 H4A . 0.980 ?
    C4 H4B . 0.980 ?
    C4 H4C . 0.980 ?
    C5 H5A . 0.980 ?
    C5 H5B . 0.980 ?
    C5 H5C . 0.980 ?
    C6 H6A . 0.980 ?
    C6 H6B . 0.980 ?
    C6 H6C . 0.980 ?
    C7 C11 . 1.395(2) ?
    C8 C9 . 1.383(3) ?
    C9 C10 . 1.370(3) ?
    C9 H9 . 0.950 ?
    C10 C11 . 1.394(2) ?
    C10 H10 . 0.950 ?
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
    C1 O1 C2 . . 106.74(12) y
    N2 N1 C1 . . 105.01(13) y
    N1 N2 C2 . . 110.86(12) y
    N1 N2 C3 . . 121.08(14) y
    C2 N2 C3 . . 127.35(13) y
    C8 N3 C7 . . 117.74(15) y
    N1 C1 O1 . . 116.63(14) ?
    N1 C1 C7 . . 125.84(15) ?
    O1 C1 C7 . . 117.42(14) ?
    O1 C2 N2 . . 99.48(11) ?
    O1 C2 C5 . . 108.65(14) ?
    N2 C2 C5 . . 111.81(14) ?
    O1 C2 C6 . . 107.83(13) ?
    N2 C2 C6 . . 114.05(14) ?
    C5 C2 C6 . . 113.84(14) ?
    O2 C3 N2 . . 120.47(16) ?
    O2 C3 C4 . . 123.71(16) ?
    N2 C3 C4 . . 115.82(14) ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C2 C5 H5A . . 109.5 ?
    C2 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C2 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C2 C6 H6A . . 109.5 ?
    C2 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C2 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N3 C7 C11 . . 121.64(15) ?
    N3 C7 C1 . . 114.10(14) ?
    C11 C7 C1 . . 124.23(15) ?
    N3 C8 C9 . . 125.05(17) ?
    N3 C8 Cl1 . . 116.35(13) ?
    C9 C8 Cl1 . . 118.59(14) ?
    C8 C9 C10 . . 117.40(16) ?
    C8 C9 H9 . . 121.3 ?
    C10 C9 H9 . . 121.3 ?
    C11 C10 C9 . . 119.43(16) ?
    C11 C10 H10 . . 120.3 ?
    C9 C10 H10 . . 120.3 ?
    C7 C11 C10 . . 118.71(16) ?
    C7 C11 Cl2 . . 123.14(13) ?
    C10 C11 Cl2 . . 118.14(13) ?
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
    C9 H9 O2 1_655 0.95 2.43 3.092(2) 127 y
    C6 H6B N1 3_665 0.98 2.59 3.526(2) 161 y
    C4 H4B Cl1 4_576 0.98 2.89 3.672(2) 138 y
