2-Hydr-oxy-5-nitro-benzaldehyde 2,4-dinitro-phenyl-hydrazone.

In the title compound, C(13)H(9)N(5)O(7), one of the nitro groups is twisted away from the attached benzene ring by 16.21 (8)°. The dihedral angle between the two benzene rings is 4.63 (1)°. The mol-ecular structure is stabilized by intra-molecular N-H⋯O and O-H⋯N hydrogen bonds which generate an S(6) ring motif. The mol-ecules pack as layers parallel to the ab plane; mol-ecules of adjacent layers are linked into chains along the [101] direction through N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Cordis et al. (1998 ▶); Fun et al. (1996 ▶); Guillaumont & Nakamura (2000 ▶); Hanoune et al. (2006 ▶); Lamberton et al. (1974 ▶); Niknam et al. (2005 ▶); Raj & Kurup (2007 ▶); Salhin et al. (2007 ▶); Shan, Xu et al. (2003 ▶); Shan, Yu et al. (2003 ▶); Tameem et al. (2007 ▶); Uchiyama et al. (2003 ▶); Vogel et al. (2000 ▶); Zegota (1999 ▶); Zlotorzynska & Lai (1999 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9N5O7

M = 347.25

Monoclinic,

a = 12.7543 (5) Å

b = 8.1898 (3) Å

c = 13.8618 (5) Å

β = 112.683 (2)°

V = 1335.94 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 100.0 (1) K

0.29 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.960, T max = 0.985

24539 measured reflections

5195 independent reflections

3513 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.09

5195 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005825/ci2567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005825/ci2567Isup2.hkl

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

C13H9N5O7	F000 = 712
Mr = 347.25	Dx = 1.726 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3255 reflections
a = 12.7543 (5) Å	θ = 2.8–33.1º
b = 8.1898 (3) Å	µ = 0.14 mm−1
c = 13.8618 (5) Å	T = 100.0 (1) K
β = 112.683 (2)º	Block, orange
V = 1335.94 (9) Å3	0.29 × 0.27 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3513 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1	Rint = 0.056
ω scans	θmax = 33.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	θmin = 2.8º
Tmin = 0.960, Tmax = 0.985	h = −19→19
24539 measured reflections	k = −10→12
5195 independent reflections	l = −21→20

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.0132P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.050	(Δ/σ)max = 0.001
wR(F2) = 0.145	Δρmax = 0.47 e Å−3
S = 1.09	Δρmin = −0.33 e Å−3
5195 reflections	Extinction correction: none
234 parameters

Geometry. Experimental. The low-temperature data was collected with the Oxford Crysosystem Cobra low-temperature attachement.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.

	x	y	z	Uiso*/Ueq
O1	0.71240 (8)	0.91583 (13)	0.22343 (8)	0.0228 (2)
O2	0.61439 (9)	1.12841 (14)	0.22968 (8)	0.0282 (2)
O3	0.39947 (10)	1.41385 (15)	−0.08171 (9)	0.0340 (3)
O4	0.45224 (10)	1.41148 (14)	−0.21219 (8)	0.0307 (3)
O5	0.94762 (8)	0.81549 (12)	−0.11896 (7)	0.0189 (2)
O6	1.34597 (9)	0.33913 (14)	0.11735 (8)	0.0300 (3)
O7	1.29887 (9)	0.41281 (13)	0.24496 (8)	0.0259 (2)
N1	0.80661 (9)	0.91651 (14)	0.08340 (9)	0.0164 (2)
N2	0.87737 (9)	0.86266 (13)	0.03680 (8)	0.0157 (2)
N3	0.66026 (9)	1.04241 (14)	0.18460 (8)	0.0187 (2)
N4	0.46053 (10)	1.36459 (15)	−0.12555 (9)	0.0208 (2)
N5	1.28791 (9)	0.41996 (14)	0.15301 (9)	0.0184 (2)
C1	0.64902 (11)	1.08800 (16)	0.07968 (9)	0.0160 (2)
C2	0.56488 (11)	1.20121 (16)	0.02874 (10)	0.0179 (2)
H2A	0.5209	1.2465	0.062	0.021*
C3	0.54779 (10)	1.24505 (16)	−0.07199 (10)	0.0172 (2)
C4	0.61284 (11)	1.17695 (16)	−0.12363 (10)	0.0171 (2)
H4A	0.5993	1.2067	−0.1921	0.02*
C5	0.69644 (11)	1.06624 (16)	−0.07233 (10)	0.0165 (2)
H5A	0.7392	1.0211	−0.1069	0.02*
C6	0.71925 (10)	1.01896 (15)	0.03210 (9)	0.0150 (2)
C7	0.96469 (10)	0.78013 (15)	0.09632 (9)	0.0151 (2)
H7A	0.9782	0.7678	0.1668	0.018*
C8	1.04195 (10)	0.70636 (15)	0.05474 (9)	0.0142 (2)
C9	1.03109 (10)	0.72528 (15)	−0.05001 (9)	0.0151 (2)
C10	1.10725 (11)	0.64726 (16)	−0.08556 (10)	0.0168 (2)
H10A	1.1009	0.6634	−0.154	0.02*
C11	1.19152 (10)	0.54678 (16)	−0.02006 (10)	0.0169 (2)
H11A	1.2412	0.4933	−0.044	0.02*
C12	1.20051 (10)	0.52732 (15)	0.08265 (10)	0.0159 (2)
C13	1.12875 (10)	0.60635 (15)	0.12052 (10)	0.0153 (2)
H13A	1.1382	0.593	0.19	0.018*
H1N1	0.8262 (16)	0.891 (2)	0.1508 (16)	0.038 (5)*
H1O5	0.905 (2)	0.854 (3)	−0.082 (2)	0.067 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0238 (5)	0.0253 (5)	0.0220 (5)	0.0056 (4)	0.0118 (4)	0.0049 (4)
O2	0.0377 (6)	0.0307 (6)	0.0253 (5)	0.0079 (5)	0.0222 (5)	−0.0004 (4)
O3	0.0317 (6)	0.0461 (7)	0.0298 (6)	0.0207 (5)	0.0181 (5)	0.0077 (5)
O4	0.0379 (6)	0.0342 (6)	0.0228 (5)	0.0153 (5)	0.0150 (5)	0.0087 (4)
O5	0.0201 (4)	0.0210 (5)	0.0162 (4)	0.0047 (4)	0.0076 (3)	0.0023 (3)
O6	0.0284 (5)	0.0335 (6)	0.0285 (5)	0.0145 (5)	0.0114 (4)	0.0014 (4)
O7	0.0269 (5)	0.0307 (6)	0.0197 (5)	0.0070 (4)	0.0086 (4)	0.0059 (4)
N1	0.0163 (5)	0.0196 (5)	0.0155 (5)	0.0030 (4)	0.0085 (4)	0.0005 (4)
N2	0.0158 (5)	0.0157 (5)	0.0177 (5)	0.0000 (4)	0.0089 (4)	−0.0017 (4)
N3	0.0193 (5)	0.0220 (6)	0.0183 (5)	−0.0015 (4)	0.0112 (4)	−0.0006 (4)
N4	0.0209 (5)	0.0224 (6)	0.0204 (5)	0.0049 (4)	0.0097 (4)	0.0004 (4)
N5	0.0170 (5)	0.0177 (5)	0.0203 (5)	0.0010 (4)	0.0070 (4)	0.0005 (4)
C1	0.0177 (5)	0.0183 (6)	0.0144 (5)	−0.0009 (4)	0.0088 (4)	−0.0011 (4)
C2	0.0176 (5)	0.0191 (6)	0.0195 (6)	0.0006 (5)	0.0099 (5)	−0.0033 (5)
C3	0.0161 (5)	0.0174 (6)	0.0194 (6)	0.0029 (5)	0.0081 (5)	0.0005 (4)
C4	0.0194 (6)	0.0174 (6)	0.0158 (5)	−0.0005 (5)	0.0085 (4)	−0.0005 (4)
C5	0.0169 (5)	0.0185 (6)	0.0160 (5)	0.0001 (5)	0.0085 (4)	−0.0023 (4)
C6	0.0147 (5)	0.0150 (6)	0.0163 (5)	−0.0019 (4)	0.0070 (4)	−0.0017 (4)
C7	0.0161 (5)	0.0151 (6)	0.0158 (5)	−0.0009 (4)	0.0081 (4)	−0.0004 (4)
C8	0.0151 (5)	0.0143 (5)	0.0142 (5)	−0.0009 (4)	0.0068 (4)	−0.0013 (4)
C9	0.0156 (5)	0.0142 (6)	0.0156 (5)	−0.0007 (4)	0.0062 (4)	−0.0002 (4)
C10	0.0190 (6)	0.0181 (6)	0.0156 (5)	−0.0011 (5)	0.0093 (4)	−0.0010 (4)
C11	0.0159 (5)	0.0174 (6)	0.0200 (6)	−0.0012 (4)	0.0096 (5)	−0.0024 (4)
C12	0.0134 (5)	0.0140 (6)	0.0190 (6)	0.0010 (4)	0.0048 (4)	0.0005 (4)
C13	0.0160 (5)	0.0147 (6)	0.0161 (5)	−0.0009 (4)	0.0072 (4)	0.0000 (4)

O1—N3	1.2372 (15)	C2—H2A	0.93
O2—N3	1.2291 (15)	C3—C4	1.4035 (18)
O3—N4	1.2262 (15)	C4—C5	1.3711 (18)
O4—N4	1.2259 (15)	C4—H4A	0.93
O5—C9	1.3446 (15)	C5—C6	1.4159 (17)
O5—H1O5	0.92 (3)	C5—H5A	0.93
O6—N5	1.2302 (15)	C7—C8	1.4514 (17)
O7—N5	1.2288 (14)	C7—H7A	0.93
N1—C6	1.3565 (16)	C8—C13	1.3962 (17)
N1—N2	1.3697 (15)	C8—C9	1.4128 (16)
N1—H1N1	0.89 (2)	C9—C10	1.4014 (18)
N2—C7	1.2920 (16)	C10—C11	1.3799 (18)
N3—C1	1.4541 (16)	C10—H10A	0.93
N4—C3	1.4530 (17)	C11—C12	1.3927 (17)
N5—C12	1.4589 (16)	C11—H11A	0.93
C1—C2	1.3876 (18)	C12—C13	1.3795 (17)
C1—C6	1.4187 (17)	C13—H13A	0.93
C2—C3	1.3753 (17)
C9—O5—H1O5	105.4 (15)	C4—C5—H5A	119.2
C6—N1—N2	120.62 (11)	C6—C5—H5A	119.2
C6—N1—H1N1	122.4 (13)	N1—C6—C5	120.57 (11)
N2—N1—H1N1	116.6 (13)	N1—C6—C1	122.75 (11)
C7—N2—N1	115.45 (10)	C5—C6—C1	116.66 (11)
O2—N3—O1	122.71 (11)	N2—C7—C8	120.94 (11)
O2—N3—C1	118.60 (11)	N2—C7—H7A	119.5
O1—N3—C1	118.64 (11)	C8—C7—H7A	119.5
O4—N4—O3	123.45 (12)	C13—C8—C9	118.32 (11)
O4—N4—C3	118.12 (11)	C13—C8—C7	118.27 (11)
O3—N4—C3	118.43 (11)	C9—C8—C7	123.37 (11)
O7—N5—O6	123.08 (11)	O5—C9—C10	117.82 (11)
O7—N5—C12	118.31 (11)	O5—C9—C8	121.85 (11)
O6—N5—C12	118.60 (11)	C10—C9—C8	120.32 (11)
C2—C1—C6	122.19 (11)	C11—C10—C9	120.67 (11)
C2—C1—N3	116.05 (11)	C11—C10—H10A	119.7
C6—C1—N3	121.76 (11)	C9—C10—H10A	119.7
C3—C2—C1	118.67 (12)	C10—C11—C12	118.49 (12)
C3—C2—H2A	120.7	C10—C11—H11A	120.8
C1—C2—H2A	120.7	C12—C11—H11A	120.8
C2—C3—C4	121.38 (12)	C13—C12—C11	122.02 (11)
C2—C3—N4	119.01 (11)	C13—C12—N5	118.45 (11)
C4—C3—N4	119.61 (11)	C11—C12—N5	119.53 (11)
C5—C4—C3	119.51 (12)	C12—C13—C8	120.14 (11)
C5—C4—H4A	120.2	C12—C13—H13A	119.9
C3—C4—H4A	120.2	C8—C13—H13A	119.9
C4—C5—C6	121.55 (12)
C6—N1—N2—C7	172.84 (11)	C2—C1—C6—C5	−2.48 (18)
O2—N3—C1—C2	−15.33 (17)	N3—C1—C6—C5	176.74 (11)
O1—N3—C1—C2	162.33 (11)	N1—N2—C7—C8	175.64 (11)
O2—N3—C1—C6	165.40 (12)	N2—C7—C8—C13	−174.24 (11)
O1—N3—C1—C6	−16.94 (18)	N2—C7—C8—C9	3.12 (19)
C6—C1—C2—C3	1.35 (19)	C13—C8—C9—O5	177.95 (11)
N3—C1—C2—C3	−177.92 (11)	C7—C8—C9—O5	0.58 (19)
C1—C2—C3—C4	0.5 (2)	C13—C8—C9—C10	−1.09 (18)
C1—C2—C3—N4	−179.46 (11)	C7—C8—C9—C10	−178.46 (11)
O4—N4—C3—C2	174.55 (13)	O5—C9—C10—C11	−176.95 (11)
O3—N4—C3—C2	−5.12 (19)	C8—C9—C10—C11	2.12 (19)
O4—N4—C3—C4	−5.37 (19)	C9—C10—C11—C12	−1.25 (19)
O3—N4—C3—C4	174.96 (13)	C10—C11—C12—C13	−0.63 (19)
C2—C3—C4—C5	−1.0 (2)	C10—C11—C12—N5	179.16 (11)
N4—C3—C4—C5	178.90 (11)	O7—N5—C12—C13	−4.77 (17)
C3—C4—C5—C6	−0.22 (19)	O6—N5—C12—C13	174.17 (12)
N2—N1—C6—C5	2.89 (18)	O7—N5—C12—C11	175.44 (12)
N2—N1—C6—C1	−175.04 (11)	O6—N5—C12—C11	−5.62 (18)
C4—C5—C6—N1	−176.16 (12)	C11—C12—C13—C8	1.65 (19)
C4—C5—C6—C1	1.89 (18)	N5—C12—C13—C8	−178.14 (11)
C2—C1—C6—N1	175.52 (12)	C9—C8—C13—C12	−0.75 (18)
N3—C1—C6—N1	−5.25 (19)	C7—C8—C13—C12	176.75 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4i	0.89 (2)	2.54 (2)	3.0666 (15)	118 (2)
N1—H1N1···O1	0.89 (2)	2.07 (2)	2.6477 (15)	121 (2)
O5—H1O5···N2	0.92 (3)	1.82 (3)	2.6656 (14)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4i	0.89 (2)	2.54 (2)	3.0666 (15)	118 (2)
N1—H1N1⋯O1	0.89 (2)	2.07 (2)	2.6477 (15)	121 (2)
O5—H1O5⋯N2	0.92 (3)	1.82 (3)	2.6656 (14)	150 (2)

Symmetry code: (i) .