2-Hydroxy-3-methoxybenzaldehyde 2,4-dinitrophenylhydrazone pyridine monosolvate.

The Schiff base molecule of the title compound, C(14)H(12)N(4)O(6)·C(5)H(5)N, was obtained from the condensation reaction of 2-hy-droxy-3-meth-oxy-benzaldehyde and 2,4-dinitro-phenyl-hydrazine. The C=N bond of the Schiff base has a trans arrangement and the dihedral angle between the two benzene rings is 3.49 (10)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, O-H⋯O hydrogen bonds link the Schiff base mol-ecules.

Related literature

For background to Schiff bases, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For a related structure, see: Ohba (1996 ▶).

Experimental

Crystal data

C14H12N4O6·C5H5N

M = 411.38

Triclinic,

a = 6.9020 (18) Å

b = 7.6240 (12) Å

c = 19.073 (3) Å

α = 95.112 (13)°

β = 91.199 (17)°

γ = 107.024 (19)°

V = 954.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.973, T max = 0.978

7517 measured reflections

4401 independent reflections

1852 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.143

S = 0.82

4401 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029971/hb5577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029971/hb5577Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H12N4O6·C5H5N	Z = 2
Mr = 411.38	F(000) = 418
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9020 (18) Å	Cell parameters from 1741 reflections
b = 7.6240 (12) Å	θ = 3.2–29.3°
c = 19.073 (3) Å	µ = 0.11 mm−1
α = 95.112 (13)°	T = 293 K
β = 91.199 (17)°	Block, red
γ = 107.024 (19)°	0.21 × 0.19 × 0.17 mm
V = 954.7 (3) Å3

Bruker SMART CCD diffractometer	4401 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 29.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→9
Tmin = 0.973, Tmax = 0.978	k = −10→8
7517 measured reflections	l = −23→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 0.82	w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3
4401 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. 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.

Refinement. 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.

	x	y	z	Uiso*/Ueq
N1	0.7466 (3)	0.0112 (2)	0.01896 (10)	0.0424 (5)
N3	0.6500 (3)	−0.4948 (2)	−0.11703 (12)	0.0485 (5)
O1	0.7209 (2)	0.00916 (18)	0.23110 (8)	0.0549 (5)
H1B	0.6315	−0.0690	0.2069	0.082*
C1	0.7623 (3)	0.1767 (3)	0.13134 (12)	0.0390 (5)
N2	0.7090 (3)	−0.1535 (2)	−0.02176 (10)	0.0429 (5)
H2A	0.6742	−0.2561	−0.0030	0.051*
C2	0.7567 (3)	0.1720 (3)	0.20412 (13)	0.0412 (6)
O3	0.6370 (3)	−0.5111 (2)	−0.05341 (11)	0.0677 (5)
C12	0.7671 (3)	−0.1328 (3)	−0.23637 (12)	0.0386 (5)
O2	0.7845 (3)	0.3159 (2)	0.31832 (9)	0.0670 (5)
C8	0.7250 (3)	0.0051 (3)	0.08483 (13)	0.0399 (5)
H8A	0.6856	−0.1080	0.1035	0.048*
C10	0.7001 (3)	−0.3115 (2)	−0.13946 (12)	0.0367 (5)
C3	0.7921 (3)	0.3370 (3)	0.24820 (13)	0.0476 (6)
C6	0.8044 (3)	0.3474 (3)	0.10356 (13)	0.0477 (6)
H6A	0.8102	0.3526	0.0551	0.057*
C14	0.7760 (3)	0.0185 (3)	−0.12116 (12)	0.0400 (5)
H14A	0.7952	0.1268	−0.0918	0.048*
C11	0.7186 (3)	−0.3009 (3)	−0.21097 (12)	0.0399 (6)
H11A	0.6983	−0.4075	−0.2415	0.048*
O4	0.6221 (3)	−0.6271 (2)	−0.16096 (10)	0.0679 (6)
N4	0.7912 (3)	−0.1221 (3)	−0.31121 (11)	0.0534 (5)
C5	0.8368 (3)	0.5061 (3)	0.14741 (15)	0.0549 (7)
H5A	0.8634	0.6184	0.1284	0.066*
C13	0.7946 (3)	0.0271 (3)	−0.19136 (12)	0.0407 (6)
H13A	0.8261	0.1407	−0.2096	0.049*
O5	0.8451 (3)	0.0308 (2)	−0.33278 (10)	0.0713 (6)
C9	0.7280 (3)	−0.1511 (3)	−0.09170 (12)	0.0354 (5)
C4	0.8307 (3)	0.5021 (3)	0.21998 (15)	0.0533 (7)
H4A	0.8528	0.6111	0.2493	0.064*
O6	0.7599 (3)	−0.2658 (3)	−0.35043 (10)	0.0813 (6)
C18	0.3624 (4)	0.0818 (3)	−0.36369 (12)	0.0432 (6)
H18A	0.3344	0.0297	−0.3214	0.052*
C7	0.8415 (5)	0.4749 (4)	0.36657 (16)	0.0861 (10)
H7A	0.8292	0.4398	0.4138	0.129*
H7B	0.7546	0.5500	0.3588	0.129*
H7C	0.9796	0.5435	0.3601	0.129*
N5	0.2789 (4)	0.0847 (4)	−0.48479 (16)	0.0962 (9)
C19	0.2479 (4)	0.0124 (4)	−0.42066 (17)	0.0663 (8)
H19A	0.1386	−0.0923	−0.4179	0.080*
C17	0.5183 (5)	0.2274 (4)	−0.36801 (16)	0.0732 (9)
H17A	0.6012	0.2766	−0.3277	0.088*
C15	0.4455 (5)	0.2404 (4)	−0.48748 (17)	0.0736 (8)
H15A	0.4736	0.2948	−0.5293	0.088*
C16	0.5660 (5)	0.3114 (4)	−0.42861 (18)	0.0760 (9)
H16A	0.6783	0.4146	−0.4293	0.091*

	U11	U22	U33	U12	U13	U23
N1	0.0478 (11)	0.0423 (10)	0.0358 (13)	0.0098 (8)	0.0002 (9)	0.0099 (9)
N3	0.0542 (13)	0.0366 (11)	0.0584 (16)	0.0161 (9)	0.0098 (11)	0.0130 (11)
O1	0.0749 (11)	0.0411 (9)	0.0432 (11)	0.0083 (7)	−0.0017 (9)	0.0069 (7)
C1	0.0306 (11)	0.0417 (12)	0.0435 (16)	0.0081 (9)	−0.0015 (10)	0.0074 (10)
N2	0.0563 (12)	0.0342 (9)	0.0379 (12)	0.0107 (8)	0.0036 (10)	0.0109 (8)
C2	0.0362 (12)	0.0440 (12)	0.0425 (16)	0.0099 (9)	−0.0003 (11)	0.0060 (11)
O3	0.1054 (15)	0.0491 (10)	0.0544 (14)	0.0253 (9)	0.0186 (11)	0.0247 (9)
C12	0.0393 (12)	0.0444 (12)	0.0343 (14)	0.0142 (9)	0.0037 (10)	0.0097 (10)
O2	0.0895 (13)	0.0634 (10)	0.0400 (12)	0.0122 (9)	0.0021 (10)	−0.0021 (9)
C8	0.0380 (13)	0.0438 (12)	0.0390 (15)	0.0116 (9)	−0.0002 (11)	0.0123 (10)
C10	0.0346 (12)	0.0317 (11)	0.0448 (15)	0.0093 (9)	0.0043 (10)	0.0104 (10)
C3	0.0421 (13)	0.0523 (14)	0.0452 (17)	0.0094 (10)	0.0008 (12)	0.0036 (12)
C6	0.0434 (13)	0.0469 (13)	0.0480 (16)	0.0039 (10)	−0.0011 (12)	0.0123 (11)
C14	0.0472 (13)	0.0343 (11)	0.0377 (15)	0.0100 (9)	0.0037 (11)	0.0070 (10)
C11	0.0398 (13)	0.0358 (11)	0.0430 (16)	0.0102 (9)	0.0029 (11)	0.0016 (10)
O4	0.0970 (14)	0.0336 (9)	0.0729 (14)	0.0187 (9)	0.0124 (11)	0.0037 (9)
N4	0.0635 (14)	0.0614 (13)	0.0397 (14)	0.0235 (11)	0.0074 (10)	0.0110 (11)
C5	0.0510 (15)	0.0418 (13)	0.069 (2)	0.0058 (11)	0.0002 (13)	0.0178 (12)
C13	0.0457 (13)	0.0338 (11)	0.0427 (15)	0.0083 (9)	0.0071 (11)	0.0150 (10)
O5	0.1020 (15)	0.0721 (12)	0.0476 (13)	0.0311 (10)	0.0184 (10)	0.0256 (9)
C9	0.0302 (11)	0.0384 (11)	0.0376 (15)	0.0082 (9)	0.0039 (10)	0.0101 (10)
C4	0.0508 (15)	0.0434 (13)	0.060 (2)	0.0067 (11)	−0.0025 (13)	−0.0023 (12)
O6	0.1247 (17)	0.0754 (12)	0.0429 (12)	0.0308 (11)	0.0063 (11)	−0.0032 (10)
C18	0.0617 (15)	0.0504 (13)	0.0200 (13)	0.0172 (12)	0.0036 (11)	0.0137 (10)
C7	0.115 (3)	0.084 (2)	0.053 (2)	0.0256 (18)	0.0025 (18)	−0.0192 (16)
N5	0.102 (2)	0.120 (2)	0.080 (2)	0.0501 (18)	0.0147 (17)	0.0221 (18)
C19	0.0695 (19)	0.0749 (17)	0.058 (2)	0.0208 (14)	0.0169 (16)	0.0237 (15)
C17	0.099 (2)	0.0744 (19)	0.054 (2)	0.0404 (17)	−0.0206 (18)	0.0007 (16)
C15	0.084 (2)	0.0792 (19)	0.067 (2)	0.0295 (17)	0.0219 (18)	0.0330 (17)
C16	0.081 (2)	0.0683 (17)	0.079 (3)	0.0186 (15)	−0.0033 (19)	0.0186 (17)

N1—C8	1.272 (3)	C14—C13	1.353 (3)
N1—N2	1.369 (2)	C14—C9	1.408 (3)
N3—O4	1.219 (2)	C14—H14A	0.9300
N3—O3	1.233 (2)	C11—H11A	0.9300
N3—C10	1.444 (3)	N4—O5	1.227 (2)
O1—C2	1.344 (2)	N4—O6	1.231 (2)
O1—H1B	0.8200	C5—C4	1.388 (4)
C1—C2	1.393 (3)	C5—H5A	0.9300
C1—C6	1.402 (3)	C13—H13A	0.9300
C1—C8	1.467 (3)	C4—H4A	0.9300
N2—C9	1.344 (3)	C18—C19	1.305 (3)
N2—H2A	0.8600	C18—C17	1.310 (3)
C2—C3	1.405 (3)	C18—H18A	0.9300
C12—C11	1.362 (3)	C7—H7A	0.9600
C12—C13	1.389 (3)	C7—H7B	0.9600
C12—N4	1.447 (3)	C7—H7C	0.9600
O2—C3	1.362 (3)	N5—C19	1.381 (4)
O2—C7	1.407 (3)	N5—C15	1.396 (4)
C8—H8A	0.9300	C19—H19A	0.9300
C10—C11	1.380 (3)	C17—C16	1.371 (4)
C10—C9	1.421 (3)	C17—H17A	0.9300
C3—C4	1.370 (3)	C15—C16	1.354 (4)
C6—C5	1.366 (3)	C15—H15A	0.9300
C6—H6A	0.9300	C16—H16A	0.9300
C8—N1—N2	117.18 (18)	O5—N4—C12	118.34 (19)
O4—N3—O3	122.35 (19)	O6—N4—C12	119.0 (2)
O4—N3—C10	119.5 (2)	C6—C5—C4	121.0 (2)
O3—N3—C10	118.15 (19)	C6—C5—H5A	119.5
C2—O1—H1B	109.5	C4—C5—H5A	119.5
C2—C1—C6	119.0 (2)	C14—C13—C12	120.38 (19)
C2—C1—C8	120.1 (2)	C14—C13—H13A	119.8
C6—C1—C8	120.8 (2)	C12—C13—H13A	119.8
C9—N2—N1	118.40 (17)	N2—C9—C14	119.45 (18)
C9—N2—H2A	120.8	N2—C9—C10	124.01 (19)
N1—N2—H2A	120.8	C14—C9—C10	116.5 (2)
O1—C2—C1	119.27 (19)	C3—C4—C5	119.7 (2)
O1—C2—C3	121.0 (2)	C3—C4—H4A	120.2
C1—C2—C3	119.7 (2)	C5—C4—H4A	120.2
C11—C12—C13	120.8 (2)	C19—C18—C17	117.8 (3)
C11—C12—N4	119.12 (19)	C19—C18—H18A	121.1
C13—C12—N4	120.05 (19)	C17—C18—H18A	121.1
C3—O2—C7	118.4 (2)	O2—C7—H7A	109.5
N1—C8—C1	119.9 (2)	O2—C7—H7B	109.5
N1—C8—H8A	120.1	H7A—C7—H7B	109.5
C1—C8—H8A	120.1	O2—C7—H7C	109.5
C11—C10—C9	121.50 (19)	H7A—C7—H7C	109.5
C11—C10—N3	115.69 (19)	H7B—C7—H7C	109.5
C9—C10—N3	122.8 (2)	C19—N5—C15	116.6 (3)
O2—C3—C4	125.1 (2)	C18—C19—N5	124.1 (3)
O2—C3—C2	114.6 (2)	C18—C19—H19A	118.0
C4—C3—C2	120.4 (2)	N5—C19—H19A	118.0
C5—C6—C1	120.3 (2)	C18—C17—C16	123.7 (3)
C5—C6—H6A	119.9	C18—C17—H17A	118.1
C1—C6—H6A	119.9	C16—C17—H17A	118.1
C13—C14—C9	121.41 (19)	C16—C15—N5	119.4 (3)
C13—C14—H14A	119.3	C16—C15—H15A	120.3
C9—C14—H14A	119.3	N5—C15—H15A	120.3
C12—C11—C10	119.34 (19)	C15—C16—C17	118.3 (3)
C12—C11—H11A	120.3	C15—C16—H16A	120.8
C10—C11—H11A	120.3	C17—C16—H16A	120.8
O5—N4—O6	122.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O4i	0.82	2.53	3.319 (2)	162.
N2—H2A···O3	0.86	2.03	2.635 (2)	126.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O4i	0.82	2.53	3.319 (2)	162
N2—H2A⋯O3	0.86	2.03	2.635 (2)	126

Symmetry code: (i) .