##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-07-25
_journal_date_accepted     2010-07-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2204
_journal_page_last     o2204
_journal_paper_category     QO
_journal_coeditor_code     HB5577
_publ_contact_author_name     'Zhao, Lin-xiu'
_publ_contact_author_address
;
College of Chemical Engineering and Environment,
North University of China,
Taiyuan 030051
People's Republic of China
;
_publ_contact_author_email     zhaolinxiu126@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhao, Lin-xiu'
;
College of Chemical Engineering and Environment,
North University of China,
Taiyuan 030051
People's Republic of China
;
    'Cao, Duan-lin'
;
College of Chemical Engineering and Environment,
North University of China,
Taiyuan 030051
People's Republic of China
;
    'Cui, Jian-lan'
;
College of Chemical Engineering and Environment,
North University of China,
Taiyuan 030051
People's Republic of China
;
data_I
_chemical_name_systematic
;
2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H12 N4 O6, C5 H5 N'
_chemical_formula_sum     'C19 H17 N5 O6'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C14 H12 N4 O6, C5 H5 N'
_chemical_formula_weight     411.38
_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     6.9020(18)
_cell_length_b     7.6240(12)
_cell_length_c     19.073(3)
_cell_angle_alpha     95.112(13)
_cell_angle_beta     91.199(17)
_cell_angle_gamma     107.024(19)
_cell_volume     954.7(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1741
_cell_measurement_theta_min     3.16
_cell_measurement_theta_max     29.31
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.431
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     418
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.973
_exptl_absorpt_correction_T_max     0.978
_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     'Bruker SMART CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7517
_diffrn_reflns_av_R_equivalents     0.0202
_diffrn_reflns_av_sigmaI/netI     0.0766
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     29.31
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.840
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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 >
σ(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     4401
_reflns_number_gt     1852
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1249
_refine_ls_R_factor_gt     0.0513
_refine_ls_wR_factor_gt     0.1266
_refine_ls_wR_factor_ref     0.1433
_refine_ls_goodness_of_fit_ref     0.818
_refine_ls_restrained_S_all     0.818
_refine_ls_number_reflns     4401
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] 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     0.311
_refine_diff_density_min     -0.382
_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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.7466(3) 0.0112(2) 0.01896(10) 0.0424(5) Uani d . 1 . .
    N N3 0.6500(3) -0.4948(2) -0.11703(12) 0.0485(5) Uani d . 1 . .
    O O1 0.7209(2) 0.00916(18) 0.23110(8) 0.0549(5) Uani d . 1 . .
    H H1B 0.6315 -0.0690 0.2069 0.082 Uiso calc R 1 . .
    C C1 0.7623(3) 0.1767(3) 0.13134(12) 0.0390(5) Uani d . 1 . .
    N N2 0.7090(3) -0.1535(2) -0.02176(10) 0.0429(5) Uani d . 1 . .
    H H2A 0.6742 -0.2561 -0.0030 0.051 Uiso calc R 1 . .
    C C2 0.7567(3) 0.1720(3) 0.20412(13) 0.0412(6) Uani d . 1 . .
    O O3 0.6370(3) -0.5111(2) -0.05341(11) 0.0677(5) Uani d . 1 . .
    C C12 0.7671(3) -0.1328(3) -0.23637(12) 0.0386(5) Uani d . 1 . .
    O O2 0.7845(3) 0.3159(2) 0.31832(9) 0.0670(5) Uani d . 1 . .
    C C8 0.7250(3) 0.0051(3) 0.08483(13) 0.0399(5) Uani d . 1 . .
    H H8A 0.6856 -0.1080 0.1035 0.048 Uiso calc R 1 . .
    C C10 0.7001(3) -0.3115(2) -0.13946(12) 0.0367(5) Uani d . 1 . .
    C C3 0.7921(3) 0.3370(3) 0.24820(13) 0.0476(6) Uani d . 1 . .
    C C6 0.8044(3) 0.3474(3) 0.10356(13) 0.0477(6) Uani d . 1 . .
    H H6A 0.8102 0.3526 0.0551 0.057 Uiso calc R 1 . .
    C C14 0.7760(3) 0.0185(3) -0.12116(12) 0.0400(5) Uani d . 1 . .
    H H14A 0.7952 0.1268 -0.0918 0.048 Uiso calc R 1 . .
    C C11 0.7186(3) -0.3009(3) -0.21097(12) 0.0399(6) Uani d . 1 . .
    H H11A 0.6983 -0.4075 -0.2415 0.048 Uiso calc R 1 . .
    O O4 0.6221(3) -0.6271(2) -0.16096(10) 0.0679(6) Uani d . 1 . .
    N N4 0.7912(3) -0.1221(3) -0.31121(11) 0.0534(5) Uani d . 1 . .
    C C5 0.8368(3) 0.5061(3) 0.14741(15) 0.0549(7) Uani d . 1 . .
    H H5A 0.8634 0.6184 0.1284 0.066 Uiso calc R 1 . .
    C C13 0.7946(3) 0.0271(3) -0.19136(12) 0.0407(6) Uani d . 1 . .
    H H13A 0.8261 0.1407 -0.2096 0.049 Uiso calc R 1 . .
    O O5 0.8451(3) 0.0308(2) -0.33278(10) 0.0713(6) Uani d . 1 . .
    C C9 0.7280(3) -0.1511(3) -0.09170(12) 0.0354(5) Uani d . 1 . .
    C C4 0.8307(3) 0.5021(3) 0.21998(15) 0.0533(7) Uani d . 1 . .
    H H4A 0.8528 0.6111 0.2493 0.064 Uiso calc R 1 . .
    O O6 0.7599(3) -0.2658(3) -0.35043(10) 0.0813(6) Uani d . 1 . .
    C C18 0.3624(4) 0.0818(3) -0.36369(12) 0.0432(6) Uani d . 1 . .
    H H18A 0.3344 0.0297 -0.3214 0.052 Uiso calc R 1 . .
    C C7 0.8415(5) 0.4749(4) 0.36657(16) 0.0861(10) Uani d . 1 . .
    H H7A 0.8292 0.4398 0.4138 0.129 Uiso calc R 1 . .
    H H7B 0.7546 0.5500 0.3588 0.129 Uiso calc R 1 . .
    H H7C 0.9796 0.5435 0.3601 0.129 Uiso calc R 1 . .
    N N5 0.2789(4) 0.0847(4) -0.48479(16) 0.0962(9) Uani d . 1 . .
    C C19 0.2479(4) 0.0124(4) -0.42066(17) 0.0663(8) Uani d . 1 . .
    H H19A 0.1386 -0.0923 -0.4179 0.080 Uiso calc R 1 . .
    C C17 0.5183(5) 0.2274(4) -0.36801(16) 0.0732(9) Uani d . 1 . .
    H H17A 0.6012 0.2766 -0.3277 0.088 Uiso calc R 1 . .
    C C15 0.4455(5) 0.2404(4) -0.48748(17) 0.0736(8) Uani d . 1 . .
    H H15A 0.4736 0.2948 -0.5293 0.088 Uiso calc R 1 . .
    C C16 0.5660(5) 0.3114(4) -0.42861(18) 0.0760(9) Uani d . 1 . .
    H H16A 0.6783 0.4146 -0.4293 0.091 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C8 . 1.272(3) ?
    N1 N2 . 1.369(2) ?
    N3 O4 . 1.219(2) ?
    N3 O3 . 1.233(2) ?
    N3 C10 . 1.444(3) ?
    O1 C2 . 1.344(2) ?
    O1 H1B . 0.8200 ?
    C1 C2 . 1.393(3) ?
    C1 C6 . 1.402(3) ?
    C1 C8 . 1.467(3) ?
    N2 C9 . 1.344(3) ?
    N2 H2A . 0.8600 ?
    C2 C3 . 1.405(3) ?
    C12 C11 . 1.362(3) ?
    C12 C13 . 1.389(3) ?
    C12 N4 . 1.447(3) ?
    O2 C3 . 1.362(3) ?
    O2 C7 . 1.407(3) ?
    C8 H8A . 0.9300 ?
    C10 C11 . 1.380(3) ?
    C10 C9 . 1.421(3) ?
    C3 C4 . 1.370(3) ?
    C6 C5 . 1.366(3) ?
    C6 H6A . 0.9300 ?
    C14 C13 . 1.353(3) ?
    C14 C9 . 1.408(3) ?
    C14 H14A . 0.9300 ?
    C11 H11A . 0.9300 ?
    N4 O5 . 1.227(2) ?
    N4 O6 . 1.231(2) ?
    C5 C4 . 1.388(4) ?
    C5 H5A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C4 H4A . 0.9300 ?
    C18 C19 . 1.305(3) ?
    C18 C17 . 1.310(3) ?
    C18 H18A . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    N5 C19 . 1.381(4) ?
    N5 C15 . 1.396(4) ?
    C19 H19A . 0.9300 ?
    C17 C16 . 1.371(4) ?
    C17 H17A . 0.9300 ?
    C15 C16 . 1.354(4) ?
    C15 H15A . 0.9300 ?
    C16 H16A . 0.9300 ?
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 N1 N2 . . 117.18(18) ?
    O4 N3 O3 . . 122.35(19) ?
    O4 N3 C10 . . 119.5(2) ?
    O3 N3 C10 . . 118.15(19) ?
    C2 O1 H1B . . 109.5 ?
    C2 C1 C6 . . 119.0(2) ?
    C2 C1 C8 . . 120.1(2) ?
    C6 C1 C8 . . 120.8(2) ?
    C9 N2 N1 . . 118.40(17) ?
    C9 N2 H2A . . 120.8 ?
    N1 N2 H2A . . 120.8 ?
    O1 C2 C1 . . 119.27(19) ?
    O1 C2 C3 . . 121.0(2) ?
    C1 C2 C3 . . 119.7(2) ?
    C11 C12 C13 . . 120.8(2) ?
    C11 C12 N4 . . 119.12(19) ?
    C13 C12 N4 . . 120.05(19) ?
    C3 O2 C7 . . 118.4(2) ?
    N1 C8 C1 . . 119.9(2) ?
    N1 C8 H8A . . 120.1 ?
    C1 C8 H8A . . 120.1 ?
    C11 C10 C9 . . 121.50(19) ?
    C11 C10 N3 . . 115.69(19) ?
    C9 C10 N3 . . 122.8(2) ?
    O2 C3 C4 . . 125.1(2) ?
    O2 C3 C2 . . 114.6(2) ?
    C4 C3 C2 . . 120.4(2) ?
    C5 C6 C1 . . 120.3(2) ?
    C5 C6 H6A . . 119.9 ?
    C1 C6 H6A . . 119.9 ?
    C13 C14 C9 . . 121.41(19) ?
    C13 C14 H14A . . 119.3 ?
    C9 C14 H14A . . 119.3 ?
    C12 C11 C10 . . 119.34(19) ?
    C12 C11 H11A . . 120.3 ?
    C10 C11 H11A . . 120.3 ?
    O5 N4 O6 . . 122.7(2) ?
    O5 N4 C12 . . 118.34(19) ?
    O6 N4 C12 . . 119.0(2) ?
    C6 C5 C4 . . 121.0(2) ?
    C6 C5 H5A . . 119.5 ?
    C4 C5 H5A . . 119.5 ?
    C14 C13 C12 . . 120.38(19) ?
    C14 C13 H13A . . 119.8 ?
    C12 C13 H13A . . 119.8 ?
    N2 C9 C14 . . 119.45(18) ?
    N2 C9 C10 . . 124.01(19) ?
    C14 C9 C10 . . 116.5(2) ?
    C3 C4 C5 . . 119.7(2) ?
    C3 C4 H4A . . 120.2 ?
    C5 C4 H4A . . 120.2 ?
    C19 C18 C17 . . 117.8(3) ?
    C19 C18 H18A . . 121.1 ?
    C17 C18 H18A . . 121.1 ?
    O2 C7 H7A . . 109.5 ?
    O2 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O2 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C19 N5 C15 . . 116.6(3) ?
    C18 C19 N5 . . 124.1(3) ?
    C18 C19 H19A . . 118.0 ?
    N5 C19 H19A . . 118.0 ?
    C18 C17 C16 . . 123.7(3) ?
    C18 C17 H17A . . 118.1 ?
    C16 C17 H17A . . 118.1 ?
    C16 C15 N5 . . 119.4(3) ?
    C16 C15 H15A . . 120.3 ?
    N5 C15 H15A . . 120.3 ?
    C15 C16 C17 . . 118.3(3) ?
    C15 C16 H16A . . 120.8 ?
    C17 C16 H16A . . 120.8 ?
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
    O1 H1B O4 2_645 0.82 2.53 3.319(2) 161.8
    N2 H2A O3 . 0.86 2.03 2.635(2) 126.3
