##############################################################################
###                                                                        ###
###        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     2006-02-21
_journal_date_accepted     2006-03-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      4
_journal_page_first     o1424
_journal_page_last     o1425
_journal_paper_category     EO
_journal_coeditor_code     IS2007
_publ_contact_author_name     'Prof. Li, Yi-Zhi'
_publ_contact_author_address
;
Coordination Chemistry Institute,
State Key Laboratory of Coordination Chemistry
Nanjing University,
Nanjing, 210093
P.R.China
;
_publ_contact_author_email     llyyjz@nju.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
3,5-Bis(salicylideneamino)-1H-1,2,4-triazole methanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Cheng, Ru-Mei'
;
Coordination Chemistry Institute
State Key Laboratory of Coordination Chemistry
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Li, Yi-Zhi'
;
Coordination Chemistry Institute
State Key Laboratory of Coordination Chemistry
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Ou, Sheng-Ju'
;
Coordination Chemistry Institute
State Key Laboratory of Coordination Chemistry
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Chen, Xue-Tai'
;
Coordination Chemistry Institute
State Key Laboratory of Coordination Chemistry
Nanjing University
Nanjing 210093
People's Republic of China
;
data_I
_chemical_name_systematic
;
3,5-Bis(salicylideneamino)-1H-1,2,4-triazole methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H13 N5 O2, C H4 O'
_chemical_formula_sum     'C17 H17 N5 O3'
_chemical_formula_iupac     'C16 H13 N5 O2, C H4 O'
_chemical_formula_weight     339.36
_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     5.8562(7)
_cell_length_b     9.1651(12)
_cell_length_c     31.907(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.332(3)
_cell_angle_gamma     90.00
_cell_volume     1712.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     428
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     17.47
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.316
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     712
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.97
_exptl_absorpt_correction_T_max     0.98
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9110
_diffrn_reflns_av_R_equivalents     0.0532
_diffrn_reflns_av_sigmaI/netI     0.0922
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -39
_diffrn_reflns_limit_l_max     30
_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     3374
_reflns_number_gt     1686
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1325
_refine_ls_R_factor_gt     0.0655
_refine_ls_wR_factor_gt     0.1437
_refine_ls_wR_factor_ref     0.1585
_refine_ls_goodness_of_fit_ref     0.964
_refine_ls_restrained_S_all     0.964
_refine_ls_number_reflns     3374
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0643P)²] 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     0.175
_refine_diff_density_min     -0.177
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Bruker, 2000)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_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 1.1721(5) 0.1470(4) 0.19836(9) 0.0652(8) Uani d . 1 . .
    C C2 1.2701(6) 0.0591(4) 0.22949(11) 0.0790(10) Uani d . 1 . .
    H H2 1.4055 0.0092 0.2244 0.095 Uiso calc R 1 . .
    C C3 1.1631(7) 0.0473(4) 0.26788(11) 0.0796(10) Uani d . 1 . .
    H H3 1.2297 -0.0096 0.2888 0.096 Uiso calc R 1 . .
    C C4 0.9612(6) 0.1174(4) 0.27589(10) 0.0745(10) Uani d . 1 . .
    H H4 0.8917 0.1082 0.3019 0.089 Uiso calc R 1 . .
    C C5 0.8627(5) 0.2017(4) 0.24505(9) 0.0662(9) Uani d . 1 . .
    H H5 0.7254 0.2491 0.2504 0.079 Uiso calc R 1 . .
    C C6 0.9648(5) 0.2175(3) 0.20585(9) 0.0576(7) Uani d . 1 . .
    C C7 0.8511(5) 0.3055(3) 0.17455(8) 0.0559(7) Uani d . 1 . .
    H H7 0.7088 0.3451 0.1806 0.067 Uiso calc R 1 . .
    C C8 0.8159(5) 0.4212(3) 0.11162(8) 0.0541(7) Uani d . 1 . .
    C C9 0.5763(5) 0.5677(3) 0.08722(8) 0.0496(7) Uani d . 1 . .
    C C10 0.2655(5) 0.6937(3) 0.11037(9) 0.0560(7) Uani d . 1 . .
    H H10 0.2905 0.6456 0.1357 0.067 Uiso calc R 1 . .
    C C11 0.0777(5) 0.7952(3) 0.10708(9) 0.0561(7) Uani d . 1 . .
    C C12 -0.0566(5) 0.8191(4) 0.14269(10) 0.0705(9) Uani d . 1 . .
    H H12 -0.0231 0.7704 0.1676 0.085 Uiso calc R 1 . .
    C C13 -0.2383(5) 0.9147(4) 0.14086(11) 0.0742(10) Uani d . 1 . .
    H H13 -0.3299 0.9294 0.1642 0.089 Uiso calc R 1 . .
    C C14 -0.2829(6) 0.9889(4) 0.10366(12) 0.0804(10) Uani d . 1 . .
    H H14 -0.4062 1.0528 0.1024 0.097 Uiso calc R 1 . .
    C C15 -0.1486(6) 0.9701(4) 0.06862(11) 0.0802(10) Uani d . 1 . .
    H H15 -0.1794 1.0224 0.0442 0.096 Uiso calc R 1 . .
    C C16 0.0318(5) 0.8732(4) 0.07009(10) 0.0657(9) Uani d . 1 . .
    C C17 1.3512(8) 0.2341(5) 0.03626(13) 0.1053(15) Uani d . 1 . .
    H H17A 1.3444 0.2278 0.0663 0.158 Uiso calc R 1 . .
    H H17B 1.5074 0.2273 0.0275 0.158 Uiso calc R 1 . .
    H H17C 1.2649 0.1556 0.0241 0.158 Uiso calc R 1 . .
    N N1 0.7299(4) 0.5392(3) 0.05723(7) 0.0585(7) Uani d . 1 . .
    H H1B 0.746(5) 0.576(3) 0.0301(10) 0.070 Uiso d . 1 . .
    N N2 0.8900(4) 0.4436(3) 0.07248(7) 0.0586(7) Uani d . 1 . .
    N N3 0.9409(4) 0.3308(3) 0.13849(7) 0.0564(6) Uani d . 1 . .
    N N4 0.6240(4) 0.4962(3) 0.12198(6) 0.0529(6) Uani d . 1 . .
    N N5 0.4002(4) 0.6673(3) 0.07929(7) 0.0550(6) Uani d . 1 . .
    O O1 1.2836(4) 0.1605(3) 0.16170(7) 0.0864(8) Uani d . 1 . .
    H H1A 1.184(6) 0.216(4) 0.1388(11) 0.104 Uiso d . 1 . .
    O O2 0.1601(5) 0.8552(3) 0.03571(7) 0.0970(9) Uani d . 1 . .
    H H2A 0.282(7) 0.774(5) 0.0403(12) 0.116 Uiso d . 1 . .
    O O3 1.2594(4) 0.3676(3) 0.02309(7) 0.0820(8) Uani d . 1 . .
    H H3A 1.133(6) 0.374(4) 0.0384(11) 0.098 Uiso d . 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.
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
  2.9453 (0.0073) x + 7.2897 (0.0079) y + 10.7001 (0.0396) z = 6.6354 (0.0098)
 *    0.0104 (0.0025)  C1
 *   -0.0084 (0.0028)  C2
 *    0.0013 (0.0028)  C3
 *    0.0039 (0.0026)  C4
 *   -0.0019 (0.0024)  C5
 *   -0.0053 (0.0023)  C6
 Rms deviation of fitted atoms =   0.0062
  3.2637 (0.0064) x + 7.0279 (0.0085) y + 10.0583 (0.0424) z = 6.7486 (0.0022)
 Angle to previous plane (with approximate esd) =  3.70 ( 0.20 )
 *   -0.0012 (0.0016)  N1
 *    0.0027 (0.0016)  N2
 *   -0.0032 (0.0017)  C8
 *    0.0023 (0.0017)  N4
 *   -0.0006 (0.0017)  C9
 Rms deviation of fitted atoms =   0.0022
  3.5359 (0.0063) x + 6.7679 (0.0085) y + 9.4679 (0.0428) z = 6.6826 (0.0079)
 Angle to previous plane (with approximate esd) =  3.29 ( 0.20 )
 *   -0.0124 (0.0022)  C11
 *    0.0115 (0.0024)  C12
 *   -0.0010 (0.0024)  C13
 *   -0.0086 (0.0026)  C14
 *    0.0075 (0.0026)  C15
 *    0.0030 (0.0024)  C16
 Rms deviation of fitted atoms =   0.0084
;
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 O1 . 1.349(3) ?
    C1 C6 . 1.397(4) ?
    C1 C2 . 1.399(4) ?
    C2 C3 . 1.383(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.371(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.375(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.397(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.443(4) ?
    C7 N3 . 1.289(3) ?
    C7 H7 . 0.9300 ?
    C8 N2 . 1.340(3) ?
    C8 N4 . 1.360(3) ?
    C8 N3 . 1.397(3) ?
    C9 N4 . 1.317(3) ?
    C9 N1 . 1.343(3) ?
    C9 N5 . 1.399(3) ?
    C10 N5 . 1.293(3) ?
    C10 C11 . 1.444(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.403(4) ?
    C11 C16 . 1.404(4) ?
    C12 C13 . 1.380(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.391(5) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.381(5) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.381(4) ?
    C15 H15 . 0.9300 ?
    C16 O2 . 1.343(4) ?
    C17 O3 . 1.400(5) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    N1 N2 . 1.371(3) ?
    N1 H1B . 0.94(3) ?
    N2 O3 . 2.773(3) ?
    O1 H1A . 1.06(4) ?
    O2 H2A . 1.05(4) ?
    O3 H3A . 0.89(4) ?
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
    O1 C1 C6 . . 122.1(3) ?
    O1 C1 C2 . . 118.0(3) ?
    C6 C1 C2 . . 119.9(3) ?
    C3 C2 C1 . . 119.2(3) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C4 C3 C2 . . 121.6(3) ?
    C4 C3 H3 . . 119.2 ?
    C2 C3 H3 . . 119.2 ?
    C3 C4 C5 . . 119.3(3) ?
    C3 C4 H4 . . 120.4 ?
    C5 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 121.2(3) ?
    C4 C5 H5 . . 119.4 ?
    C6 C5 H5 . . 119.4 ?
    C1 C6 C5 . . 118.8(3) ?
    C1 C6 C7 . . 122.6(3) ?
    C5 C6 C7 . . 118.6(3) ?
    N3 C7 C6 . . 121.9(3) ?
    N3 C7 H7 . . 119.0 ?
    C6 C7 H7 . . 119.0 ?
    N2 C8 N4 . . 114.9(2) ?
    N2 C8 N3 . . 119.4(2) ?
    N4 C8 N3 . . 125.6(2) ?
    N4 C9 N1 . . 111.3(3) ?
    N4 C9 N5 . . 129.0(2) ?
    N1 C9 N5 . . 119.6(2) ?
    N5 C10 C11 . . 122.1(3) ?
    N5 C10 H10 . . 118.9 ?
    C11 C10 H10 . . 118.9 ?
    C12 C11 C16 . . 119.7(3) ?
    C12 C11 C10 . . 118.2(3) ?
    C16 C11 C10 . . 122.1(3) ?
    C13 C12 C11 . . 120.0(3) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C13 C14 . . 119.2(3) ?
    C12 C13 H13 . . 120.4 ?
    C14 C13 H13 . . 120.4 ?
    C15 C14 C13 . . 121.6(3) ?
    C15 C14 H14 . . 119.2 ?
    C13 C14 H14 . . 119.2 ?
    C16 C15 C14 . . 119.4(3) ?
    C16 C15 H15 . . 120.3 ?
    C14 C15 H15 . . 120.3 ?
    O2 C16 C15 . . 118.8(3) ?
    O2 C16 C11 . . 121.2(3) ?
    C15 C16 C11 . . 119.9(3) ?
    O3 C17 H17A . . 109.5 ?
    O3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C9 N1 N2 . . 109.3(2) ?
    C9 N1 H1B . . 131.4(19) ?
    N2 N1 H1B . . 119.2(19) ?
    C8 N2 N1 . . 101.8(2) ?
    C8 N2 O3 . . 138.50(19) ?
    N1 N2 O3 . . 119.55(16) ?
    C7 N3 C8 . . 116.1(2) ?
    C9 N4 C8 . . 102.6(2) ?
    C10 N5 C9 . . 115.8(2) ?
    C1 O1 H1A . . 112.1(19) ?
    C16 O2 H2A . . 111(2) ?
    C17 O3 N2 . . 110.4(2) ?
    C17 O3 H3A . . 102(2) ?
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
    O2 H2A N5 . 1.05(4) 1.72(4) 2.618(3) 141(3)
    O1 H1A N3 . 1.06(4) 1.77(4) 2.645(3) 137(3)
    O3 H3A N2 . 0.89(4) 1.91(4) 2.773(3) 164(4)
    N1 H1B O3 3_765 0.94(3) 1.77(3) 2.702(3) 172(3)
    C15 H15 O2 3_575 0.93 2.79 3.694(4) 164
    C14 H14 O1 1_365 0.93 2.81 3.522(4) 134
    C4 H4 N4 2_645 0.93 2.64 3.481(4) 151
