##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
9-(1,2,4-Triazol-1-yl)anthracene
;
_chemical_formula_moiety     'C16 H11 N3'
_chemical_formula_sum     'C16 H11 N3'
_chemical_formula_iupac     'C16 H11 N3'
_chemical_formula_weight     245.28
_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     8.5580(17)
_cell_length_b     8.9289(18)
_cell_length_c     9.0170(18)
_cell_angle_alpha     63.57(3)
_cell_angle_beta     75.43(3)
_cell_angle_gamma     77.80(3)
_cell_volume     593.2(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1267
_cell_measurement_theta_min     2.4753
_cell_measurement_theta_max     27.8844
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'Colorless'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     256
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9817
_exptl_absorpt_correction_T_max     0.9850
_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     'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4470
_diffrn_reflns_av_R_equivalents     0.0380
_diffrn_reflns_av_sigmaI/netI     0.0519
_diffrn_reflns_theta_min     2.48
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_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     2053
_reflns_number_gt     1624
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0833
_refine_ls_R_factor_gt     0.0615
_refine_ls_wR_factor_gt     0.1255
_refine_ls_wR_factor_ref     0.1372
_refine_ls_goodness_of_fit_ref     1.117
_refine_ls_restrained_S_all     1.117
_refine_ls_number_reflns     2053
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0545P)²+0.1412P] 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     0.180
_refine_diff_density_min     -0.264
_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'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction     'CrystalClear'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXTL'
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
    C C1 1.0212(3) 0.3020(3) 0.2577(3) 0.0213(5) Uani d . 1 . .
    C C2 1.0449(3) 0.3347(3) 0.3913(3) 0.0231(5) Uani d . 1 . .
    H H2 0.9621 0.3212 0.4842 0.028 Uiso calc R 1 . .
    C C3 1.1863(3) 0.3850(3) 0.3850(3) 0.0264(6) Uani d . 1 . .
    H H3 1.1994 0.4054 0.4735 0.032 Uiso calc R 1 . .
    C C4 1.3144(3) 0.4070(3) 0.2444(3) 0.0277(6) Uani d . 1 . .
    H H4 1.4107 0.4414 0.2416 0.033 Uiso calc R 1 . .
    C C5 1.2974(3) 0.3781(3) 0.1144(3) 0.0255(6) Uani d . 1 . .
    H H5 1.3825 0.3924 0.0234 0.031 Uiso calc R 1 . .
    C C6 1.1504(3) 0.3258(3) 0.1153(3) 0.0217(5) Uani d . 1 . .
    C C7 1.1293(3) 0.2950(3) -0.0173(3) 0.0241(5) Uani d . 1 . .
    H H7 1.2129 0.3116 -0.1099 0.029 Uiso calc R 1 . .
    C C8 0.9887(3) 0.2407(3) -0.0157(3) 0.0219(5) Uani d . 1 . .
    C C9 0.9710(3) 0.2043(3) -0.1493(3) 0.0261(6) Uani d . 1 . .
    H H9 1.0550 0.2197 -0.2414 0.031 Uiso calc R 1 . .
    C C10 0.8342(3) 0.1479(3) -0.1439(3) 0.0295(6) Uani d . 1 . .
    H H10 0.8254 0.1238 -0.2316 0.035 Uiso calc R 1 . .
    C C11 0.7041(3) 0.1252(3) -0.0056(3) 0.0291(6) Uani d . 1 . .
    H H11 0.6101 0.0873 -0.0040 0.035 Uiso calc R 1 . .
    C C12 0.7148(3) 0.1578(3) 0.1245(3) 0.0269(6) Uani d . 1 . .
    H H12 0.6280 0.1425 0.2139 0.032 Uiso calc R 1 . .
    C C13 0.8576(3) 0.2153(3) 0.1259(3) 0.0223(5) Uani d . 1 . .
    C C14 0.8790(3) 0.2467(3) 0.2583(3) 0.0214(5) Uani d . 1 . .
    C C15 0.6928(3) 0.0793(3) 0.5191(3) 0.0285(6) Uani d . 1 . .
    H H15 0.7345 -0.0271 0.5230 0.034 Uiso calc R 1 . .
    C C16 0.5572(3) 0.2780(3) 0.5699(3) 0.0286(6) Uani d . 1 . .
    H H16 0.4792 0.3366 0.6233 0.034 Uiso calc R 1 . .
    N N1 0.7494(2) 0.2221(2) 0.4010(2) 0.0225(5) Uani d . 1 . .
    N N2 0.6607(2) 0.3560(2) 0.4323(2) 0.0268(5) Uani d . 1 . .
    N N3 0.5709(2) 0.1080(3) 0.6291(2) 0.0325(5) 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
    C1 0.0227(12) 0.0143(12) 0.0235(12) 0.0016(9) -0.0051(10) -0.0059(10)
    C2 0.0252(13) 0.0223(13) 0.0213(12) -0.0023(10) -0.0015(10) -0.0102(10)
    C3 0.0298(13) 0.0257(14) 0.0269(13) -0.0013(10) -0.0082(10) -0.0130(11)
    C4 0.0237(13) 0.0267(14) 0.0326(13) -0.0069(10) -0.0063(10) -0.0098(11)
    C5 0.0222(13) 0.0244(13) 0.0252(12) -0.0027(10) -0.0013(10) -0.0079(11)
    C6 0.0224(12) 0.0176(12) 0.0222(12) 0.0023(9) -0.0056(10) -0.0069(10)
    C7 0.0226(12) 0.0241(13) 0.0222(12) -0.0009(10) -0.0002(10) -0.0093(10)
    C8 0.0231(12) 0.0195(12) 0.0209(12) 0.0005(10) -0.0058(10) -0.0068(10)
    C9 0.0319(14) 0.0235(13) 0.0206(12) 0.0011(10) -0.0054(10) -0.0088(10)
    C10 0.0418(15) 0.0244(14) 0.0262(13) -0.0026(11) -0.0123(11) -0.0111(11)
    C11 0.0322(14) 0.0256(14) 0.0330(14) -0.0051(11) -0.0128(11) -0.0107(11)
    C12 0.0243(13) 0.0259(14) 0.0298(13) -0.0027(10) -0.0036(10) -0.0116(11)
    C13 0.0224(12) 0.0190(12) 0.0237(12) 0.0008(10) -0.0049(10) -0.0083(10)
    C14 0.0199(12) 0.0185(12) 0.0221(12) -0.0013(9) 0.0005(10) -0.0079(10)
    C15 0.0292(14) 0.0281(14) 0.0276(13) -0.0074(11) -0.0010(11) -0.0114(11)
    C16 0.0226(13) 0.0386(16) 0.0271(13) -0.0038(11) -0.0012(10) -0.0172(12)
    N1 0.0213(10) 0.0253(11) 0.0227(10) -0.0040(8) 0.0003(8) -0.0131(9)
    N2 0.0220(11) 0.0320(12) 0.0291(11) -0.0005(9) -0.0001(9) -0.0186(10)
    N3 0.0313(12) 0.0346(13) 0.0300(12) -0.0086(9) -0.0001(9) -0.0128(10)
_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
    C1 C14 . 1.405(3) ?
    C1 C2 . 1.428(3) ?
    C1 C6 . 1.435(3) ?
    C2 C3 . 1.357(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.420(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.354(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.429(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.399(3) ?
    C7 C8 . 1.384(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.429(3) ?
    C8 C13 . 1.438(3) ?
    C9 C10 . 1.351(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.417(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.356(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.427(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.402(3) ?
    C14 N1 . 1.437(3) ?
    C15 N3 . 1.315(3) ?
    C15 N1 . 1.336(3) ?
    C15 H15 . 0.9300 ?
    C16 N2 . 1.322(3) ?
    C16 N3 . 1.356(3) ?
    C16 H16 . 0.9300 ?
    N1 N2 . 1.377(3) ?
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
    C14 C1 C2 . . 123.7(2) ?
    C14 C1 C6 . . 118.1(2) ?
    C2 C1 C6 . . 118.2(2) ?
    C3 C2 C1 . . 121.0(2) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 120.6(2) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C5 C4 C3 . . 120.5(2) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 120.8(2) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C7 C6 C5 . . 122.1(2) ?
    C7 C6 C1 . . 119.1(2) ?
    C5 C6 C1 . . 118.8(2) ?
    C8 C7 C6 . . 122.4(2) ?
    C8 C7 H7 . . 118.8 ?
    C6 C7 H7 . . 118.8 ?
    C7 C8 C9 . . 121.8(2) ?
    C7 C8 C13 . . 119.6(2) ?
    C9 C8 C13 . . 118.6(2) ?
    C10 C9 C8 . . 121.0(2) ?
    C10 C9 H9 . . 119.5 ?
    C8 C9 H9 . . 119.5 ?
    C9 C10 C11 . . 120.5(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 120.8(2) ?
    C12 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
    C11 C12 C13 . . 120.9(2) ?
    C11 C12 H12 . . 119.5 ?
    C13 C12 H12 . . 119.5 ?
    C14 C13 C12 . . 123.9(2) ?
    C14 C13 C8 . . 117.8(2) ?
    C12 C13 C8 . . 118.2(2) ?
    C13 C14 C1 . . 123.0(2) ?
    C13 C14 N1 . . 118.69(19) ?
    C1 C14 N1 . . 118.35(19) ?
    N3 C15 N1 . . 111.6(2) ?
    N3 C15 H15 . . 124.2 ?
    N1 C15 H15 . . 124.2 ?
    N2 C16 N3 . . 116.3(2) ?
    N2 C16 H16 . . 121.8 ?
    N3 C16 H16 . . 121.8 ?
    C15 N1 N2 . . 109.22(18) ?
    C15 N1 C14 . . 129.43(19) ?
    N2 N1 C14 . . 121.35(17) ?
    C16 N2 N1 . . 101.12(19) ?
    C15 N3 C16 . . 101.70(19) ?
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
    C14 C1 C2 C3 . . . . 178.8(2) ?
    C6 C1 C2 C3 . . . . -0.7(3) ?
    C1 C2 C3 C4 . . . . 0.2(3) ?
    C2 C3 C4 C5 . . . . 0.1(4) ?
    C3 C4 C5 C6 . . . . 0.3(3) ?
    C4 C5 C6 C7 . . . . 180.0(2) ?
    C4 C5 C6 C1 . . . . -0.9(3) ?
    C14 C1 C6 C7 . . . . 0.6(3) ?
    C2 C1 C6 C7 . . . . -179.8(2) ?
    C14 C1 C6 C5 . . . . -178.5(2) ?
    C2 C1 C6 C5 . . . . 1.1(3) ?
    C5 C6 C7 C8 . . . . 178.5(2) ?
    C1 C6 C7 C8 . . . . -0.6(3) ?
    C6 C7 C8 C9 . . . . -177.8(2) ?
    C6 C7 C8 C13 . . . . 0.4(3) ?
    C7 C8 C9 C10 . . . . 178.5(2) ?
    C13 C8 C9 C10 . . . . 0.3(3) ?
    C8 C9 C10 C11 . . . . 0.6(3) ?
    C9 C10 C11 C12 . . . . -0.7(4) ?
    C10 C11 C12 C13 . . . . -0.2(4) ?
    C11 C12 C13 C14 . . . . -178.0(2) ?
    C11 C12 C13 C8 . . . . 1.1(3) ?
    C7 C8 C13 C14 . . . . -0.2(3) ?
    C9 C8 C13 C14 . . . . 178.1(2) ?
    C7 C8 C13 C12 . . . . -179.4(2) ?
    C9 C8 C13 C12 . . . . -1.1(3) ?
    C12 C13 C14 C1 . . . . 179.5(2) ?
    C8 C13 C14 C1 . . . . 0.3(3) ?
    C12 C13 C14 N1 . . . . -0.8(3) ?
    C8 C13 C14 N1 . . . . 179.99(19) ?
    C2 C1 C14 C13 . . . . 179.9(2) ?
    C6 C1 C14 C13 . . . . -0.5(3) ?
    C2 C1 C14 N1 . . . . 0.2(3) ?
    C6 C1 C14 N1 . . . . 179.79(18) ?
    N3 C15 N1 N2 . . . . -0.1(3) ?
    N3 C15 N1 C14 . . . . -179.2(2) ?
    C13 C14 N1 C15 . . . . 68.5(3) ?
    C1 C14 N1 C15 . . . . -111.7(3) ?
    C13 C14 N1 N2 . . . . -110.6(2) ?
    C1 C14 N1 N2 . . . . 69.2(3) ?
    N3 C16 N2 N1 . . . . -0.2(3) ?
    C15 N1 N2 C16 . . . . 0.1(2) ?
    C14 N1 N2 C16 . . . . 179.39(19) ?
    N1 C15 N3 C16 . . . . 0.0(3) ?
    N2 C16 N3 C15 . . . . 0.1(3) ?
data_global
_journal_date_recd_electronic     2007-05-04
_journal_date_accepted     2007-05-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o2898
_journal_page_last     o2898
_journal_paper_category     QO
_journal_coeditor_code     WN2138
_publ_contact_author_name     'Rong Li'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering
China West Normal University
Nanchong 637002
People's Republic of China
;
_publ_contact_author_email     ronglinc@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
9-(1,2,4-Triazol-1-yl)anthracene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rong Li' .
;
College of Chemistry and Chemical Engineering
China West Normal University
Nanchong 637002
People's Republic of China
;
