5-Diethyl-amino-2-{[2-(2,4-dinitro-phen-yl)hydrazin-1-yl-idene]meth-yl}phenol.

In the title compound, C(17)H(19)N(5)O(5), obtained from the condensation reaction of 4-diethyl-amino-2-hy-droxy-benzalde-hyde and 2,4-dinitro-phenyl-hydrazine, the two benzene rings are twisted by a dihedral angle of 1.75 (12)°. The nitro groups are slightly twisted with the respect to the benzene ring to which they are attached, making dihedral angles of 8.20 (15) and 5.78 (15)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds, forming dimers through R(2) (2)(12) rings. These dimers are further linked by C-H⋯O and C-H⋯π and weak slipped π-π inter-actions [centroid-centroid distance = 3.743 (2)Å]. One of the ethyl groups is disordered over two positions, with occupancy factors in the ratio 0.72:0.28.

Related literature

For related structures, see: Baughman et al. (2004 ▶); Kuleshova et al. (2003 ▶); Ohba (1996 ▶); Okabe et al. (1993 ▶); Szczesna & Urbanczyk-Lipkowska (2002 ▶); Zhen & Han (2005 ▶). For discussion of n class="Chemical">hydrogen-bonding patterns, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H19N5O5

M = 373.37

Triclinic,

a = 8.5300 (7) Å

b = 8.5410 (4) Å

c = 12.4910 (11) Å

α = 84.554 (7)°

β = 89.733 (6)°

γ = 75.109 (7)°

V = 875.31 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.22 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.975, T max = 0.980

5395 measured reflections

3069 independent reflections

1727 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.125

S = 0.95

3069 reflections

257 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044983/dn2616sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044983/dn2616Isup2.hkl

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

C17H19N5O5	Z = 2
Mr = 373.37	F(000) = 392
Triclinic, P1	Dx = 1.417 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5300 (7) Å	Cell parameters from 2780 reflections
b = 8.5410 (4) Å	θ = 3.0–25.0°
c = 12.4910 (11) Å	µ = 0.11 mm−1
α = 84.554 (7)°	T = 293 K
β = 89.733 (6)°	Block, red
γ = 75.109 (7)°	0.22 × 0.19 × 0.17 mm
V = 875.31 (11) Å3

Bruker SMART CCD area-detector diffractometer	3069 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.975, Tmax = 0.980	k = −10→9
5395 measured reflections	l = −14→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3
3069 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.25187 (19)	0.6271 (3)	0.50881 (14)	0.0542 (6)
H1	0.1746	0.6862	0.5369	0.081*
O2	−0.5619 (2)	1.2021 (3)	0.72130 (18)	0.0859 (9)
O3	−0.4850 (2)	1.0820 (3)	0.57933 (16)	0.0674 (7)
O4	−0.1960 (3)	1.2721 (3)	0.98125 (17)	0.0822 (8)
O5	0.0601 (3)	1.1684 (3)	0.96747 (16)	0.0757 (7)
N1	−0.0540 (2)	0.8040 (3)	0.52221 (16)	0.0361 (5)
N2	−0.1829 (2)	0.9124 (3)	0.56372 (15)	0.0380 (6)
H2	−0.2768	0.9352	0.5326	0.046*
N3	−0.4544 (3)	1.1282 (3)	0.6656 (2)	0.0510 (7)
N4	−0.0803 (3)	1.1929 (3)	0.93582 (19)	0.0538 (7)
N5	0.3830 (2)	0.2866 (3)	0.22459 (17)	0.0418 (6)
C14	0.3429 (3)	0.2320 (4)	0.1233 (2)	0.0612 (9)	0.72
H14A	0.4100	0.1223	0.1194	0.073*	0.72
H14B	0.2312	0.2253	0.1268	0.073*	0.72
C15	0.3598 (5)	0.3248 (6)	0.0249 (3)	0.0738 (14)	0.72
H15A	0.4711	0.3271	0.0167	0.111*	0.72
H15B	0.2932	0.4340	0.0258	0.111*	0.72
H15C	0.3263	0.2760	−0.0342	0.111*	0.72
C14B	0.3429 (3)	0.2320 (4)	0.1233 (2)	0.0612 (9)	0.28
H14C	0.2653	0.1684	0.1407	0.073*	0.28
H14D	0.2842	0.3292	0.0796	0.073*	0.28
C15B	0.4529 (12)	0.1441 (16)	0.0563 (9)	0.067 (3)	0.28
H15D	0.4003	0.1415	−0.0110	0.101*	0.28
H15E	0.4944	0.0350	0.0892	0.101*	0.28
H15F	0.5407	0.1944	0.0441	0.101*	0.28
C1	0.0349 (3)	0.6209 (3)	0.38800 (18)	0.0316 (6)
C2	0.1988 (3)	0.5694 (3)	0.42192 (19)	0.0347 (7)
C3	0.3117 (3)	0.4608 (3)	0.36813 (19)	0.0372 (7)
H3	0.4188	0.4291	0.3931	0.045*
C4	0.2693 (3)	0.3972 (3)	0.27695 (19)	0.0340 (6)
C5	0.1057 (3)	0.4485 (3)	0.24127 (19)	0.0378 (7)
H5	0.0733	0.4094	0.1803	0.045*
C6	−0.0054 (3)	0.5558 (3)	0.29623 (19)	0.0378 (7)
H6	−0.1127	0.5868	0.2715	0.045*
C7	−0.0867 (3)	0.7351 (3)	0.4408 (2)	0.0353 (7)
H7	−0.1934	0.7603	0.4152	0.042*
C8	−0.1625 (3)	0.9827 (3)	0.65262 (19)	0.0325 (6)
C9	−0.2895 (3)	1.0890 (3)	0.7042 (2)	0.0349 (6)
C10	−0.2620 (3)	1.1567 (3)	0.79614 (19)	0.0388 (7)
H10	−0.3475	1.2254	0.8288	0.047*
C11	−0.1096 (3)	1.1223 (3)	0.83856 (19)	0.0379 (7)
C12	0.0190 (3)	1.0181 (4)	0.7912 (2)	0.0476 (8)
H12	0.1229	0.9949	0.8213	0.057*
C13	−0.0069 (3)	0.9507 (3)	0.7016 (2)	0.0420 (7)
H13	0.0803	0.8811	0.6711	0.050*
C16	0.5551 (3)	0.2546 (4)	0.2534 (2)	0.0504 (8)
H16A	0.6138	0.1567	0.2226	0.060*
H16B	0.5675	0.2336	0.3310	0.060*
C17	0.6308 (3)	0.3901 (4)	0.2167 (2)	0.0611 (9)
H17A	0.6177	0.4134	0.1401	0.092*
H17B	0.7443	0.3582	0.2356	0.092*
H17C	0.5790	0.4856	0.2508	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0419 (11)	0.0745 (17)	0.0458 (12)	−0.0051 (11)	−0.0017 (9)	−0.0321 (11)
O2	0.0393 (11)	0.118 (2)	0.0921 (17)	0.0162 (12)	−0.0029 (11)	−0.0701 (16)
O3	0.0473 (11)	0.0875 (18)	0.0636 (14)	0.0035 (11)	−0.0156 (10)	−0.0452 (13)
O4	0.0799 (16)	0.102 (2)	0.0634 (15)	−0.0050 (14)	0.0036 (13)	−0.0537 (14)
O5	0.0664 (14)	0.102 (2)	0.0637 (14)	−0.0249 (13)	−0.0202 (12)	−0.0256 (14)
N1	0.0338 (12)	0.0365 (14)	0.0357 (12)	−0.0033 (10)	0.0072 (10)	−0.0090 (11)
N2	0.0330 (12)	0.0389 (15)	0.0385 (13)	0.0000 (10)	0.0015 (10)	−0.0117 (11)
N3	0.0367 (13)	0.0542 (18)	0.0583 (16)	0.0033 (12)	−0.0024 (12)	−0.0271 (14)
N4	0.0623 (17)	0.0568 (19)	0.0433 (15)	−0.0149 (14)	−0.0056 (14)	−0.0109 (13)
N5	0.0365 (12)	0.0470 (16)	0.0454 (14)	−0.0113 (11)	0.0070 (11)	−0.0209 (12)
C14	0.0525 (18)	0.078 (3)	0.056 (2)	−0.0138 (17)	0.0129 (16)	−0.0328 (19)
C15	0.084 (3)	0.083 (4)	0.058 (3)	−0.031 (3)	0.006 (2)	0.000 (3)
C14B	0.0525 (18)	0.078 (3)	0.056 (2)	−0.0138 (17)	0.0129 (16)	−0.0328 (19)
C15B	0.057 (7)	0.083 (10)	0.074 (8)	−0.021 (6)	0.036 (6)	−0.061 (7)
C1	0.0313 (14)	0.0314 (16)	0.0318 (14)	−0.0073 (12)	0.0025 (11)	−0.0034 (12)
C2	0.0376 (15)	0.0386 (18)	0.0307 (15)	−0.0125 (13)	0.0020 (12)	−0.0089 (13)
C3	0.0272 (13)	0.0469 (18)	0.0362 (15)	−0.0047 (12)	0.0013 (12)	−0.0107 (13)
C4	0.0352 (14)	0.0326 (17)	0.0364 (15)	−0.0114 (12)	0.0064 (12)	−0.0066 (13)
C5	0.0373 (15)	0.0395 (17)	0.0386 (15)	−0.0096 (13)	0.0012 (12)	−0.0143 (13)
C6	0.0300 (14)	0.0413 (18)	0.0415 (16)	−0.0068 (12)	−0.0020 (12)	−0.0080 (14)
C7	0.0327 (14)	0.0348 (17)	0.0368 (15)	−0.0048 (12)	0.0016 (12)	−0.0068 (13)
C8	0.0365 (15)	0.0282 (16)	0.0312 (14)	−0.0054 (12)	0.0028 (12)	−0.0036 (12)
C9	0.0299 (14)	0.0336 (17)	0.0388 (15)	−0.0027 (12)	−0.0002 (12)	−0.0078 (13)
C10	0.0366 (15)	0.0381 (18)	0.0385 (16)	−0.0017 (13)	0.0024 (13)	−0.0094 (13)
C11	0.0436 (16)	0.0413 (18)	0.0295 (15)	−0.0109 (13)	−0.0022 (13)	−0.0072 (13)
C12	0.0344 (15)	0.058 (2)	0.0458 (17)	−0.0043 (14)	−0.0064 (13)	−0.0065 (16)
C13	0.0356 (15)	0.0456 (19)	0.0414 (16)	−0.0018 (13)	0.0035 (13)	−0.0110 (14)
C16	0.0351 (15)	0.049 (2)	0.066 (2)	−0.0040 (14)	0.0092 (14)	−0.0243 (16)
C17	0.0512 (18)	0.070 (2)	0.068 (2)	−0.0201 (17)	0.0168 (16)	−0.0263 (18)

O1—C2	1.359 (3)	C1—C2	1.408 (3)
O1—H1	0.8200	C1—C7	1.434 (3)
O2—N3	1.226 (3)	C2—C3	1.376 (3)
O3—N3	1.234 (3)	C3—C4	1.395 (3)
O4—N4	1.216 (3)	C3—H3	0.9300
O5—N4	1.223 (3)	C4—C5	1.412 (3)
N1—C7	1.288 (3)	C5—C6	1.369 (3)
N1—N2	1.377 (3)	C5—H5	0.9300
N2—C8	1.344 (3)	C6—H6	0.9300
N2—H2	0.8600	C7—H7	0.9300
N3—C9	1.434 (3)	C8—C13	1.414 (3)
N4—C11	1.457 (3)	C8—C9	1.419 (3)
N5—C4	1.379 (3)	C9—C10	1.381 (3)
N5—C14	1.460 (3)	C10—C11	1.356 (3)
N5—C16	1.462 (3)	C10—H10	0.9300
C14—C15	1.426 (5)	C11—C12	1.391 (4)
C14—H14A	0.9700	C12—C13	1.351 (3)
C14—H14B	0.9700	C12—H12	0.9300
C15—H15A	0.9600	C13—H13	0.9300
C15—H15B	0.9600	C16—C17	1.500 (4)
C15—H15C	0.9600	C16—H16A	0.9700
C15B—H15D	0.9600	C16—H16B	0.9700
C15B—H15E	0.9600	C17—H17A	0.9600
C15B—H15F	0.9600	C17—H17B	0.9600
C1—C6	1.402 (3)	C17—H17C	0.9600
C2—O1—H1	109.5	C4—C5—H5	119.9
C7—N1—N2	116.1 (2)	C5—C6—C1	123.1 (2)
C8—N2—N1	120.3 (2)	C5—C6—H6	118.5
C8—N2—H2	119.8	C1—C6—H6	118.5
N1—N2—H2	119.8	N1—C7—C1	122.6 (2)
O2—N3—O3	121.8 (2)	N1—C7—H7	118.7
O2—N3—C9	118.9 (2)	C1—C7—H7	118.7
O3—N3—C9	119.3 (2)	N2—C8—C13	120.1 (2)
O4—N4—O5	123.6 (3)	N2—C8—C9	124.3 (2)
O4—N4—C11	118.6 (3)	C13—C8—C9	115.7 (2)
O5—N4—C11	117.8 (3)	C10—C9—C8	121.9 (2)
C4—N5—C14	121.1 (2)	C10—C9—N3	116.3 (2)
C4—N5—C16	119.8 (2)	C8—C9—N3	121.8 (2)
C14—N5—C16	117.2 (2)	C11—C10—C9	119.6 (2)
C15—C14—N5	119.0 (3)	C11—C10—H10	120.2
C15—C14—H14A	107.6	C9—C10—H10	120.2
N5—C14—H14A	107.6	C10—C11—C12	120.8 (3)
C15—C14—H14B	107.6	C10—C11—N4	119.7 (2)
N5—C14—H14B	107.6	C12—C11—N4	119.6 (2)
H14A—C14—H14B	107.0	C13—C12—C11	120.1 (2)
H15D—C15B—H15E	109.5	C13—C12—H12	120.0
H15D—C15B—H15F	109.5	C11—C12—H12	120.0
H15E—C15B—H15F	109.5	C12—C13—C8	122.1 (3)
C6—C1—C2	116.0 (2)	C12—C13—H13	119.0
C6—C1—C7	120.4 (2)	C8—C13—H13	119.0
C2—C1—C7	123.6 (2)	N5—C16—C17	114.4 (2)
O1—C2—C3	117.4 (2)	N5—C16—H16A	108.7
O1—C2—C1	121.0 (2)	C17—C16—H16A	108.7
C3—C2—C1	121.7 (2)	N5—C16—H16B	108.7
C2—C3—C4	121.5 (2)	C17—C16—H16B	108.7
C2—C3—H3	119.3	H16A—C16—H16B	107.6
C4—C3—H3	119.3	C16—C17—H17A	109.5
N5—C4—C3	121.0 (2)	C16—C17—H17B	109.5
N5—C4—C5	121.4 (2)	H17A—C17—H17B	109.5
C3—C4—C5	117.6 (2)	C16—C17—H17C	109.5
C6—C5—C4	120.1 (2)	H17A—C17—H17C	109.5
C6—C5—H5	119.9	H17B—C17—H17C	109.5
C7—N1—N2—C8	175.9 (2)	N1—N2—C8—C9	−176.6 (2)
C4—N5—C14—C15	86.9 (4)	N2—C8—C9—C10	179.3 (2)
C16—N5—C14—C15	−77.4 (4)	C13—C8—C9—C10	0.1 (4)
C6—C1—C2—O1	178.8 (2)	N2—C8—C9—N3	1.3 (4)
C7—C1—C2—O1	−0.2 (4)	C13—C8—C9—N3	−177.9 (2)
C6—C1—C2—C3	−0.3 (3)	O2—N3—C9—C10	−8.1 (4)
C7—C1—C2—C3	−179.3 (2)	O3—N3—C9—C10	174.4 (2)
O1—C2—C3—C4	−178.8 (2)	O2—N3—C9—C8	170.0 (3)
C1—C2—C3—C4	0.3 (4)	O3—N3—C9—C8	−7.5 (4)
C14—N5—C4—C3	−173.9 (2)	C8—C9—C10—C11	0.5 (4)
C16—N5—C4—C3	−10.0 (4)	N3—C9—C10—C11	178.6 (2)
C14—N5—C4—C5	7.0 (4)	C9—C10—C11—C12	−0.8 (4)
C16—N5—C4—C5	170.8 (2)	C9—C10—C11—N4	−179.7 (2)
C2—C3—C4—N5	−179.0 (2)	O4—N4—C11—C10	5.3 (4)
C2—C3—C4—C5	0.2 (4)	O5—N4—C11—C10	−175.0 (2)
N5—C4—C5—C6	178.5 (2)	O4—N4—C11—C12	−173.7 (3)
C3—C4—C5—C6	−0.6 (4)	O5—N4—C11—C12	6.0 (4)
C4—C5—C6—C1	0.6 (4)	C10—C11—C12—C13	0.4 (4)
C2—C1—C6—C5	−0.1 (4)	N4—C11—C12—C13	179.4 (2)
C7—C1—C6—C5	178.9 (2)	C11—C12—C13—C8	0.2 (4)
N2—N1—C7—C1	179.2 (2)	N2—C8—C13—C12	−179.7 (2)
C6—C1—C7—N1	−176.6 (2)	C9—C8—C13—C12	−0.4 (4)
C2—C1—C7—N1	2.3 (4)	C4—N5—C16—C17	−72.3 (3)
N1—N2—C8—C13	2.6 (3)	C14—N5—C16—C17	92.2 (3)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.95	2.672 (3)	146
N2—H2···O3i	0.86	2.51	3.344 (3)	162
C15—H15B···O4ii	0.96	2.43	3.359 (6)	164
C14—H14C···Cg2iii	0.96	2.71	3.620 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.95	2.672 (3)	146
N2—H2⋯O3i	0.86	2.51	3.344 (3)	162
C15—H15B⋯O4ii	0.96	2.43	3.359 (6)	164
C14—H14C⋯Cg2iii	0.96	2.71	3.620 (4)	157

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