4-{[2-(2,4-Dinitro-phen-yl)hydrazinyl-idene]meth-yl}phenol ethanol hemisolvate.

In the title compound, C(13)H(10)N(4)O(5)·0.5C(2)H(5)OH, the two benzene rings form a dihedral angle of 4.29 (9)°. The ethanol solvent mol-ecule was treated as disordered between two orientations related by symmetry (center of inversion), with occupancies fixed at 0.5. The crystal packing, stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds and π-π inter-actions [indicated by the short distance of 3.7299 (7) Å between the centroids of benzene rings from neighbouring mol-ecules], exhibits short inter-molecular O⋯O contacts of 2.8226 (3) Å.

Related literature

For related structures, see: Baughman et al. (2004 ▶); Shi et al. (2008 ▶); Ji & Shi (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10N4O5·0.5C2H6O

M = 325.28

Triclinic,

a = 7.0935 (16) Å

b = 7.2888 (17) Å

c = 14.458 (3) Å

α = 100.156 (4)°

β = 96.378 (4)°

γ = 100.604 (4)°

V = 715.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.988

4065 measured reflections

2776 independent reflections

1543 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.230

S = 1.04

2776 reflections

227 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536810045782/cv2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045782/cv2785Isup2.hkl

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

C13H10N4O5·0.5C2H6O	Z = 2
Mr = 325.28	F(000) = 338
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0935 (16) Å	Cell parameters from 748 reflections
b = 7.2888 (17) Å	θ = 2.9–24.3°
c = 14.458 (3) Å	µ = 0.12 mm−1
α = 100.156 (4)°	T = 295 K
β = 96.378 (4)°	Block, brown
γ = 100.604 (4)°	0.15 × 0.12 × 0.10 mm
V = 715.2 (3) Å3

Bruker SMART CCD area-detector diffractometer	2776 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
graphite	Rint = 0.020
phi and ω scans	θmax = 26.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
Tmin = 0.982, Tmax = 0.988	k = −8→7
4065 measured reflections	l = −14→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.230	w = 1/[σ2(Fo2) + (0.1117P)2 + 0.1836P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2776 reflections	Δρmax = 0.46 e Å−3
227 parameters	Δρmin = −0.25 e Å−3
3 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (7)

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	Occ. (<1)
O1	0.6437 (4)	0.7313 (3)	0.73110 (16)	0.0700 (8)
O2	0.4959 (4)	0.5632 (3)	0.59767 (16)	0.0683 (8)
O3	0.7183 (5)	0.4849 (4)	1.00571 (18)	0.0973 (11)
O4	0.5709 (5)	0.2032 (4)	1.00864 (18)	0.1019 (12)
O5	−0.1603 (4)	−0.6843 (4)	0.20416 (18)	0.0890 (10)
H5	−0.1738	−0.6648	0.1478	0.134*
N1	0.3674 (3)	0.1977 (3)	0.57776 (16)	0.0470 (7)
H1	0.3863	0.2907	0.5452	0.070*
N2	0.2771 (3)	0.0174 (4)	0.53066 (17)	0.0479 (7)
N3	0.5558 (4)	0.5794 (4)	0.68230 (18)	0.0499 (7)
N4	0.6183 (5)	0.3288 (5)	0.9659 (2)	0.0698 (9)
C1	0.4286 (4)	0.2316 (4)	0.6718 (2)	0.0412 (7)
C2	0.5213 (4)	0.4143 (4)	0.7248 (2)	0.0420 (7)
C3	0.5848 (4)	0.4436 (4)	0.8208 (2)	0.0474 (8)
H3	0.6479	0.5642	0.8544	0.057*
C4	0.5548 (5)	0.2961 (4)	0.8656 (2)	0.0493 (8)
C5	0.4642 (5)	0.1133 (4)	0.8163 (2)	0.0511 (8)
H5A	0.4453	0.0131	0.8485	0.061*
C6	0.4040 (4)	0.0821 (4)	0.7223 (2)	0.0467 (8)
H6	0.3450	−0.0405	0.6899	0.056*
C7	0.2242 (4)	0.0014 (4)	0.4422 (2)	0.0473 (8)
H7	0.2487	0.1092	0.4157	0.057*
C8	0.1273 (4)	−0.1784 (5)	0.3812 (2)	0.0464 (8)
C9	0.0970 (5)	−0.3493 (5)	0.4128 (2)	0.0551 (9)
H9	0.1418	−0.3512	0.4755	0.066*
C10	0.0018 (5)	−0.5148 (5)	0.3525 (2)	0.0612 (9)
H10	−0.0189	−0.6280	0.3748	0.073*
C11	−0.0638 (5)	−0.5156 (5)	0.2591 (2)	0.0585 (9)
C12	−0.0313 (5)	−0.3488 (5)	0.2267 (2)	0.0617 (10)
H12	−0.0734	−0.3487	0.1635	0.074*
C13	0.0629 (4)	−0.1817 (5)	0.2868 (2)	0.0530 (8)
H13	0.0838	−0.0693	0.2638	0.064*
O6	1.0107 (12)	0.7495 (11)	0.9734 (7)	0.148 (3)	0.50
H6A	0.9238	0.6597	0.9822	0.222*	0.50
C14	0.9498 (18)	0.9229 (13)	0.9968 (12)	0.115 (5)	0.50
H14A	1.0102	0.9845	1.0602	0.138*	0.50
H14B	0.8128	0.8924	0.9983	0.138*	0.50
C15	0.965 (5)	1.042 (3)	0.9313 (12)	0.259 (14)	0.50
H15A	0.9230	1.1573	0.9555	0.388*	0.50
H15B	1.0979	1.0729	0.9223	0.388*	0.50
H15C	0.8861	0.9802	0.8717	0.388*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.1033 (19)	0.0395 (14)	0.0569 (14)	−0.0028 (12)	0.0025 (13)	0.0063 (11)
O2	0.0965 (19)	0.0546 (15)	0.0477 (14)	0.0023 (13)	−0.0027 (13)	0.0160 (11)
O3	0.137 (3)	0.078 (2)	0.0503 (15)	−0.0157 (18)	−0.0210 (16)	0.0019 (14)
O4	0.172 (3)	0.075 (2)	0.0533 (17)	0.008 (2)	−0.0009 (18)	0.0265 (15)
O5	0.111 (2)	0.0689 (18)	0.0581 (15)	−0.0248 (16)	−0.0010 (15)	−0.0114 (13)
N1	0.0544 (15)	0.0402 (14)	0.0404 (14)	0.0029 (11)	−0.0003 (11)	0.0045 (11)
N2	0.0490 (15)	0.0455 (15)	0.0426 (15)	0.0056 (11)	0.0013 (12)	−0.0009 (11)
N3	0.0627 (17)	0.0373 (15)	0.0473 (16)	0.0055 (12)	0.0062 (13)	0.0090 (11)
N4	0.102 (2)	0.057 (2)	0.0451 (17)	0.0100 (17)	−0.0015 (16)	0.0098 (15)
C1	0.0406 (15)	0.0407 (17)	0.0406 (16)	0.0074 (12)	0.0052 (12)	0.0049 (12)
C2	0.0451 (16)	0.0360 (16)	0.0441 (16)	0.0083 (12)	0.0062 (13)	0.0060 (12)
C3	0.0569 (19)	0.0370 (17)	0.0432 (17)	0.0064 (13)	0.0034 (14)	0.0003 (12)
C4	0.062 (2)	0.0447 (18)	0.0381 (16)	0.0085 (15)	0.0016 (14)	0.0058 (13)
C5	0.066 (2)	0.0380 (17)	0.0498 (18)	0.0065 (14)	0.0117 (15)	0.0129 (13)
C6	0.0561 (18)	0.0354 (16)	0.0456 (17)	0.0047 (13)	0.0054 (14)	0.0066 (13)
C7	0.0487 (17)	0.0467 (18)	0.0433 (17)	0.0051 (14)	0.0039 (14)	0.0080 (13)
C8	0.0381 (16)	0.056 (2)	0.0401 (16)	0.0039 (13)	0.0047 (13)	0.0020 (14)
C9	0.065 (2)	0.054 (2)	0.0402 (17)	0.0030 (16)	0.0031 (15)	0.0072 (14)
C10	0.071 (2)	0.054 (2)	0.054 (2)	0.0004 (17)	0.0107 (17)	0.0075 (16)
C11	0.055 (2)	0.058 (2)	0.0478 (19)	−0.0092 (16)	0.0056 (15)	−0.0063 (16)
C12	0.056 (2)	0.075 (3)	0.0406 (17)	−0.0040 (17)	−0.0054 (15)	0.0027 (16)
C13	0.0516 (18)	0.058 (2)	0.0431 (17)	0.0020 (15)	−0.0005 (14)	0.0091 (14)
O6	0.139 (7)	0.123 (7)	0.176 (8)	−0.003 (5)	0.043 (6)	0.034 (6)
C14	0.113 (9)	0.044 (5)	0.197 (16)	0.026 (5)	0.058 (10)	0.015 (7)
C15	0.35 (4)	0.24 (3)	0.20 (3)	0.10 (2)	0.06 (3)	0.01 (2)

O1—N3	1.219 (3)	C7—H7	0.9300
O2—N3	1.227 (3)	C8—C13	1.385 (4)
O3—N4	1.229 (4)	C8—C9	1.390 (5)
O4—N4	1.210 (4)	C9—C10	1.368 (4)
O5—C11	1.356 (4)	C9—H9	0.9300
O5—H5	0.8500	C10—C11	1.376 (5)
N1—C1	1.346 (3)	C10—H10	0.9300
N1—N2	1.370 (3)	C11—C12	1.369 (5)
N1—H1	0.8900	C12—C13	1.372 (4)
N2—C7	1.270 (4)	C12—H12	0.9300
N3—O2	1.227 (3)	C13—H13	0.9300
N3—C2	1.439 (4)	O6—C14	1.407 (8)
N4—O3	1.229 (4)	O6—C15i	1.827 (19)
N4—C4	1.435 (4)	O6—H6A	0.8500
C1—C6	1.410 (4)	C14—C15i	1.11 (2)
C1—C2	1.413 (4)	C14—C14i	1.20 (2)
C2—C3	1.377 (4)	C14—C15	1.394 (9)
C3—C4	1.346 (4)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.394 (4)	C15—C14i	1.11 (2)
C5—C6	1.344 (4)	C15—O6i	1.828 (19)
C5—H5A	0.9300	C15—H15A	0.9601
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.447 (4)	C15—H15C	0.9600
C11—O5—H5	105.5	C9—C10—C11	120.6 (3)
C1—N1—N2	119.9 (3)	C9—C10—H10	119.7
C1—N1—H1	120.9	C11—C10—H10	119.7
N2—N1—H1	119.2	O5—C11—C12	123.4 (3)
C7—N2—N1	114.8 (3)	O5—C11—C10	117.2 (3)
O1—N3—O2	121.8 (3)	C12—C11—C10	119.3 (3)
O1—N3—O2	121.8 (3)	C11—C12—C13	120.5 (3)
O1—N3—C2	119.3 (3)	C11—C12—H12	119.8
O2—N3—C2	119.0 (2)	C13—C12—H12	119.8
O2—N3—C2	119.0 (2)	C12—C13—C8	120.8 (3)
O4—N4—O3	122.2 (3)	C12—C13—H13	119.6
O4—N4—O3	122.2 (3)	C8—C13—H13	119.6
O4—N4—C4	119.2 (3)	C14—O6—H6A	108.9
O3—N4—C4	118.5 (3)	C15i—O6—H6A	109.4
O3—N4—C4	118.5 (3)	C15i—C14—C14i	74.4 (13)
N1—C1—C6	120.5 (3)	C15i—C14—C15	124.3 (13)
N1—C1—C2	122.8 (3)	C14i—C14—C15	49.9 (12)
C6—C1—C2	116.7 (3)	C15i—C14—O6	92.5 (13)
C3—C2—C1	121.3 (3)	C14i—C14—O6	124.7 (14)
C3—C2—N3	116.1 (3)	C15—C14—O6	117.0 (10)
C1—C2—N3	122.5 (3)	C14i—C14—H14A	65.2
C4—C3—C2	119.4 (3)	C15—C14—H14A	113.8
C4—C3—H3	120.3	O6—C14—H14A	108.3
C2—C3—H3	120.3	C15i—C14—H14B	112.3
C3—C4—C5	121.3 (3)	C14i—C14—H14B	127.7
C3—C4—N4	119.0 (3)	C15—C14—H14B	102.9
C5—C4—N4	119.7 (3)	O6—C14—H14B	107.2
C6—C5—C4	119.9 (3)	H14A—C14—H14B	106.8
C6—C5—H5A	120.0	C14i—C15—C14	55.7 (13)
C4—C5—H5A	120.0	C14i—C15—O6i	50.3 (8)
C5—C6—C1	121.3 (3)	C14—C15—O6i	90.5 (11)
C5—C6—H6	119.3	C14i—C15—H15A	81.5
C1—C6—H6	119.3	C14—C15—H15A	109.7
N2—C7—C8	122.5 (3)	C14i—C15—H15B	74.1
N2—C7—H7	118.8	C14—C15—H15B	108.2
C8—C7—H7	118.8	O6i—C15—H15B	93.5
C13—C8—C9	118.2 (3)	H15A—C15—H15B	109.5
C13—C8—C7	118.9 (3)	C14i—C15—H15C	165.6
C9—C8—C7	122.9 (3)	C14—C15—H15C	110.5
C10—C9—C8	120.5 (3)	O6i—C15—H15C	140.8
C10—C9—H9	119.7	H15A—C15—H15C	109.5
C8—C9—H9	119.7	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.89	1.97	2.605 (3)	127
O6—H6A···O3	0.85	1.86	2.702 (9)	174
O5—H5···O6ii	0.85	2.26	2.882 (9)	130
O5—H5···O4iii	0.85	2.47	3.116 (4)	133
O5—H5···O3iii	0.85	2.60	3.404 (4)	159
N1—H1···O2iv	0.89	2.63	3.449 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.89	1.97	2.605 (3)	127
O6—H6A⋯O3	0.85	1.86	2.702 (9)	174
O5—H5⋯O6i	0.85	2.26	2.882 (9)	130
O5—H5⋯O4ii	0.85	2.47	3.116 (4)	133
O5—H5⋯O3ii	0.85	2.60	3.404 (4)	159
N1—H1⋯O2iii	0.89	2.63	3.449 (4)	153

Symmetry codes: (i) ; (ii) ; (iii) .