#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227479.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227479
loop_
_publ_author_name
'Zhao, Lin-xiu'
'Cao, Duan-lin'
'Cui, Jian-lan'
_publ_section_title
;
 2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine
 monosolvate
;
_journal_coeditor_code           HB5577
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2204
_journal_paper_doi               10.1107/S1600536810029971
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 N4 O6, C5 H5 N'
_chemical_formula_moiety         'C14 H12 N4 O6, C5 H5 N'
_chemical_formula_sum            'C19 H17 N5 O6'
_chemical_formula_weight         411.38
_chemical_name_systematic
;
2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.112(13)
_cell_angle_beta                 91.199(17)
_cell_angle_gamma                107.024(19)
_cell_formula_units_Z            2
_cell_length_a                   6.9020(18)
_cell_length_b                   7.6240(12)
_cell_length_c                   19.073(3)
_cell_measurement_reflns_used    1741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.31
_cell_measurement_theta_min      3.16
_cell_volume                     954.7(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7517
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.31
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.382
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.818
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                1852
_reflns_number_total             4401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5577.cif
_cod_data_source_block           I
_cod_database_code               2227479
_cod_database_fobs_code          2227479
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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_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_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
