##############################################################################
###                                                                        ###
###        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                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Ethyl 5-[6-(furan-2-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-3-yl]-
2,6-dimethylnicotinate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 N5 O3 S'
_chemical_formula_sum     'C17 H15 N5 O3 S'
_chemical_formula_iupac     'C17 H15 N5 O3 S'
_chemical_formula_weight     369.40
_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     8.094(4)
_cell_length_b     10.535(5)
_cell_length_c     10.996(5)
_cell_angle_alpha     66.699(5)
_cell_angle_beta     73.683(5)
_cell_angle_gamma     80.998(5)
_cell_volume     825.4(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2601
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     27.31
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.486
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     384
_exptl_absorpt_coefficient_mu     0.226
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9353
_exptl_absorpt_correction_T_max     0.9457
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     296(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 diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4297
_diffrn_reflns_av_R_equivalents     0.0174
_diffrn_reflns_av_sigmaI/netI     0.0261
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_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     2860
_reflns_number_gt     2531
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0426
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.0948
_refine_ls_wR_factor_ref     0.0997
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     2860
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0502P)²+0.2861P] 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     0.221
_refine_diff_density_min     -0.249
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.013(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2000)'
_computing_publication_material     'SHELXTL (Bruker, 2000)'
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
    N N1 0.82163(19) 0.64436(15) -0.06646(15) 0.0380(4) Uani d . 1 . .
    N N2 0.6722(2) 0.25738(17) -0.06479(16) 0.0448(4) Uani d . 1 . .
    N N3 0.5890(2) 0.13509(17) -0.02295(17) 0.0473(4) Uani d . 1 . .
    N N4 0.54173(18) 0.20294(14) 0.15000(14) 0.0320(3) Uani d . 1 . .
    N N5 0.46583(19) 0.19007(14) 0.28238(15) 0.0349(3) Uani d . 1 . .
    O O1 0.19535(18) -0.07982(13) 0.53282(14) 0.0469(3) Uani d . 1 . .
    O O2 0.7628(2) 0.63716(16) 0.33760(15) 0.0646(5) Uani d . 1 . .
    O O3 0.7023(2) 0.41744(14) 0.41061(14) 0.0572(4) Uani d . 1 . .
    S S1 0.37936(6) -0.01525(5) 0.23778(5) 0.04173(16) Uani d . 1 . .
    C C1 0.8076(2) 0.65217(18) 0.05519(19) 0.0361(4) Uani d . 1 . .
    C C2 0.7476(2) 0.54134(18) 0.17662(18) 0.0337(4) Uani d . 1 . .
    C C3 0.6956(2) 0.42634(18) 0.16808(18) 0.0342(4) Uani d . 1 . .
    H H3 0.6540 0.3523 0.2477 0.041 Uiso calc R 1 . .
    C C4 0.7047(2) 0.42024(17) 0.04290(18) 0.0322(4) Uani d . 1 . .
    C C5 0.7739(2) 0.53224(18) -0.07487(18) 0.0340(4) Uani d . 1 . .
    C C6 0.8008(3) 0.5362(2) -0.21624(19) 0.0442(5) Uani d . 1 . .
    H H6A 0.8492 0.6220 -0.2808 0.066 Uiso calc R 1 . .
    H H6B 0.6922 0.5286 -0.2315 0.066 Uiso calc R 1 . .
    H H6C 0.8782 0.4604 -0.2274 0.066 Uiso calc R 1 . .
    C C7 0.8615(3) 0.7848(2) 0.0491(2) 0.0515(5) Uani d . 1 . .
    H H7A 0.8978 0.8454 -0.0444 0.077 Uiso calc R 1 . .
    H H7B 0.9552 0.7655 0.0925 0.077 Uiso calc R 1 . .
    H H7C 0.7660 0.8284 0.0955 0.077 Uiso calc R 1 . .
    C C8 0.7393(2) 0.54110(19) 0.31403(19) 0.0385(4) Uani d . 1 . .
    C C9 0.6430(2) 0.29802(18) 0.03893(18) 0.0340(4) Uani d . 1 . .
    C C10 0.5122(2) 0.10682(18) 0.10579(19) 0.0366(4) Uani d . 1 . .
    C C11 0.3772(2) 0.07975(17) 0.33896(18) 0.0352(4) Uani d . 1 . .
    C C12 0.2798(2) 0.04004(17) 0.47908(18) 0.0363(4) Uani d . 1 . .
    C C13 0.2505(3) 0.0984(2) 0.5722(2) 0.0456(5) Uani d . 1 . .
    H H13 0.2936 0.1803 0.5607 0.055 Uiso calc R 1 . .
    C C14 0.1413(3) 0.0111(2) 0.6913(2) 0.0501(5) Uani d . 1 . .
    H H14 0.0985 0.0245 0.7734 0.060 Uiso calc R 1 . .
    C C15 0.1114(3) -0.0941(2) 0.6634(2) 0.0492(5) Uani d . 1 . .
    H H15 0.0428 -0.1670 0.7245 0.059 Uiso calc R 1 . .
    C C16 0.7021(3) 0.3943(2) 0.5502(2) 0.0541(5) Uani d . 1 . .
    H H16A 0.6072 0.3378 0.6130 0.065 Uiso calc R 1 . .
    H H16B 0.6864 0.4822 0.5622 0.065 Uiso calc R 1 . .
    C C17 0.8677(3) 0.3237(2) 0.5807(2) 0.0533(5) Uani d . 1 . .
    H H17A 0.8826 0.2366 0.5692 0.080 Uiso calc R 1 . .
    H H17B 0.8664 0.3083 0.6730 0.080 Uiso calc R 1 . .
    H H17C 0.9611 0.3807 0.5195 0.080 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
    N1 C5 . 1.343(2) ?
    N1 C1 . 1.345(2) ?
    N2 C9 . 1.320(2) y
    N2 N3 . 1.398(2) y
    N3 C10 . 1.307(2) y
    N4 C10 . 1.360(2) ?
    N4 N5 . 1.372(2) ?
    N4 C9 . 1.376(2) ?
    N5 C11 . 1.300(2) ?
    O1 C15 . 1.364(2) y
    O1 C12 . 1.365(2) y
    O2 C8 . 1.193(2) ?
    O3 C8 . 1.328(2) ?
    O3 C16 . 1.455(2) ?
    S1 C10 . 1.7308(19) y
    S1 C11 . 1.7618(18) y
    C1 C2 . 1.401(3) ?
    C1 C7 . 1.499(3) ?
    C2 C3 . 1.388(2) ?
    C2 C8 . 1.492(3) ?
    C3 C4 . 1.384(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.405(2) ?
    C4 C9 . 1.472(2) ?
    C5 C6 . 1.493(3) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C11 C12 . 1.443(3) ?
    C12 C13 . 1.342(3) ?
    C13 C14 . 1.411(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.332(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.485(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 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
    C5 N1 C1 . . 121.07(15) ?
    C9 N2 N3 . . 109.45(15) ?
    C10 N3 N2 . . 105.44(14) ?
    C10 N4 N5 . . 118.56(14) ?
    C10 N4 C9 . . 106.04(15) ?
    N5 N4 C9 . . 135.33(14) ?
    C11 N5 N4 . . 107.20(14) ?
    C15 O1 C12 . . 105.97(15) ?
    C8 O3 C16 . . 118.99(15) ?
    C10 S1 C11 . . 87.13(9) y
    N1 C1 C2 . . 120.65(16) ?
    N1 C1 C7 . . 115.27(16) ?
    C2 C1 C7 . . 124.07(17) ?
    C3 C2 C1 . . 118.28(17) ?
    C3 C2 C8 . . 118.83(16) ?
    C1 C2 C8 . . 122.88(16) ?
    C4 C3 C2 . . 121.00(16) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C3 C4 C5 . . 117.68(16) ?
    C3 C4 C9 . . 119.08(16) ?
    C5 C4 C9 . . 123.23(16) ?
    N1 C5 C4 . . 121.21(16) ?
    N1 C5 C6 . . 115.29(16) ?
    C4 C5 C6 . . 123.50(16) ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C1 C7 H7A . . 109.5 ?
    C1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O2 C8 O3 . . 122.87(18) ?
    O2 C8 C2 . . 125.99(18) ?
    O3 C8 C2 . . 111.14(15) ?
    N2 C9 N4 . . 107.67(15) ?
    N2 C9 C4 . . 128.65(16) ?
    N4 C9 C4 . . 123.68(15) ?
    N3 C10 N4 . . 111.39(16) ?
    N3 C10 S1 . . 139.04(14) y
    N4 C10 S1 . . 109.55(13) y
    N5 C11 C12 . . 120.11(16) ?
    N5 C11 S1 . . 117.56(14) ?
    C12 C11 S1 . . 122.33(13) ?
    C13 C12 O1 . . 110.19(17) ?
    C13 C12 C11 . . 133.14(17) ?
    O1 C12 C11 . . 116.66(15) ?
    C12 C13 C14 . . 106.50(18) ?
    C12 C13 H13 . . 126.7 ?
    C14 C13 H13 . . 126.7 ?
    C15 C14 C13 . . 106.87(18) ?
    C15 C14 H14 . . 126.6 ?
    C13 C14 H14 . . 126.6 ?
    C14 C15 O1 . . 110.47(17) ?
    C14 C15 H15 . . 124.8 ?
    O1 C15 H15 . . 124.8 ?
    O3 C16 C17 . . 109.93(18) ?
    O3 C16 H16A . . 109.7 ?
    C17 C16 H16A . . 109.7 ?
    O3 C16 H16B . . 109.7 ?
    C17 C16 H16B . . 109.7 ?
    H16A C16 H16B . . 108.2 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 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
    _geom_hbond_publ_flag
    C3 H3 N5 . 0.93 2.31 2.982(3) 128 yes
    C13 H13 O2 2_666 0.93 2.51 3.285(3) 141 yes
    C17 H17A O1 2_656 0.96 2.56 3.424(3) 149 yes
data_global
_journal_date_recd_electronic     2007-10-23
_journal_date_accepted     2007-11-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o80
_journal_page_last     o81
_journal_paper_category     QO
_journal_coeditor_code     AV3123
_publ_contact_author_name     'Zhang, Min'
_publ_contact_author_address
;
  Department of Chemistry
  College of Science
  Shanghai University
  Shanghai 200444
  People's Republic of China
;
_publ_contact_author_email     minzhang1@yeah.net
_publ_contact_author_fax     '86 21 66133191'
_publ_contact_author_phone     '86 21 66133191'
_publ_section_title
;\
Ethyl
5-[6-(furan-2-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-3-yl]-2,6-\
dimethylnicotinate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lu, Dongliang' .
;
Department of Chemistry
College of Science
Shanghai University
Shanghai 200444
People's Republic of China
;
    'Zhang, Min' .
;
Department of Chemistry
College of Science
Shanghai University
Shanghai 200444
People's Republic of China
;
    'Song, Liping' .
;
Department of Chemistry
College of Science
Shanghai University
Shanghai 200444
People's Republic of China
;
    'Tan, Qiwen' .
;
Department of Chemistry
College of Science
Shanghai University
Shanghai 200444
People's Republic of China
;
    'Shao, Min' .
;
Instrument Analysis & Research Center
Shanghai University
Shanghai 200444
People's Republic of China
;
