N,N,N,N-Tetra-ethyl-6-{2-[(E)-1-(4-nitro-phen-yl)ethyl-idene]hydrazino}-1,3,5-triazine-2,4-diamine.

The title compound, C(19)H(28)N(8)O(2), was prepared by the reaction of N(2),N(2),N(4),N(4)-tetra-ethyl-6-hydrazino-1,3,5-triazine-2,4-diamine and 1-(4-nitro-phen-yl)ethanone in ethanol at room temperature. The mol-ecular conformation is stabilized by intra-molecular C-H⋯N hydrogen-bonding inter-actions. There are also inter-molecular N-H⋯O hydrogen bonds, and C-H⋯π and π-π inter-actions, which help to stabilize the crystal structure. The centroid-centroid distance is 3.6172 (10) Å between adjacent benzene and 1,3,5-triazine rings.

Related literature

For the antimicrobial and anticancer applications of Schiff bases, see: Tarafder et al. (2000 ▶); Deschamps et al. (2003 ▶). For the ability of Schiff bases to form intramolecular hydrogen bonds by electron coupling between acid–base centers, see: Rozwadowski et al. (1999 ▶). For a related structure, see: Jian et al. (2006 ▶).

Experimental

Crystal data

C19H28N8O2

M = 400.49

Monoclinic,

a = 12.333 (3) Å

b = 9.5286 (19) Å

c = 17.407 (4) Å

β = 92.12 (3)°

V = 2044.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

19318 measured reflections

4667 independent reflections

4054 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.05

4667 reflections

278 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025677/at2835sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025677/at2835Isup2.hkl

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

C19H28N8O2	F(000) = 856
Mr = 400.49	Dx = 1.301 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4667 reflections
a = 12.333 (3) Å	θ = 3.2–27.5°
b = 9.5286 (19) Å	µ = 0.09 mm−1
c = 17.407 (4) Å	T = 293 K
β = 92.12 (3)°	Block, yellow
V = 2044.3 (7) Å3	0.22 × 0.18 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
graphite	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −16→15
19318 measured reflections	k = −12→12
4667 independent reflections	l = −22→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.6629P] where P = (Fo2 + 2Fc2)/3
4667 reflections	(Δ/σ)max = 0.001
278 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.24 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
N6	0.86798 (7)	0.13524 (9)	0.14238 (5)	0.01620 (18)
O2	0.61084 (7)	−0.21575 (10)	−0.26492 (5)	0.0282 (2)
O1	0.71950 (7)	−0.38030 (9)	−0.29988 (5)	0.02543 (19)
N3	0.97484 (7)	−0.06303 (10)	0.12715 (5)	0.01717 (19)
N5	0.91414 (7)	0.28722 (9)	0.24899 (5)	0.01601 (19)
N4	1.01161 (7)	0.07162 (9)	0.23260 (5)	0.01529 (18)
N7	1.05089 (7)	0.22043 (9)	0.33480 (5)	0.01625 (19)
N2	0.91687 (7)	−0.09648 (9)	0.06200 (5)	0.01611 (19)
C19	0.75621 (8)	−0.27251 (11)	−0.18232 (6)	0.0168 (2)
N1	0.69125 (7)	−0.29130 (10)	−0.25356 (5)	0.0200 (2)
N8	0.77480 (7)	0.34066 (10)	0.16191 (5)	0.01862 (19)
C15	0.79067 (8)	−0.14525 (11)	−0.06617 (6)	0.0180 (2)
H15A	0.7718	−0.0751	−0.0320	0.022*
C11	0.94887 (8)	0.05417 (11)	0.16864 (6)	0.0146 (2)
C16	0.88343 (8)	−0.22754 (11)	−0.04984 (6)	0.0148 (2)
C17	0.90831 (8)	−0.33498 (11)	−0.10124 (6)	0.0168 (2)
H17A	0.9682	−0.3920	−0.0905	0.020*
C10	0.99015 (8)	0.19185 (11)	0.27004 (6)	0.0145 (2)
C18	0.84541 (8)	−0.35806 (11)	−0.16793 (6)	0.0175 (2)
H18A	0.8628	−0.4291	−0.2020	0.021*
C12	0.95244 (8)	−0.19665 (11)	0.01989 (6)	0.0151 (2)
C14	0.72719 (8)	−0.16701 (12)	−0.13212 (6)	0.0188 (2)
H14A	0.6662	−0.1120	−0.1427	0.023*
C9	0.85476 (8)	0.25133 (11)	0.18551 (6)	0.0154 (2)
C2	1.13661 (8)	0.12427 (11)	0.36176 (6)	0.0168 (2)
H2B	1.1937	0.1780	0.3879	0.020*
H2C	1.1676	0.0793	0.3176	0.020*
C13	1.05659 (10)	−0.27421 (13)	0.03706 (7)	0.0226 (2)
C3	1.02715 (9)	0.34442 (12)	0.38092 (6)	0.0200 (2)
H3D	1.0163	0.4241	0.3468	0.024*
H3E	1.0896	0.3646	0.4146	0.024*
C6	0.69842 (9)	0.30243 (12)	0.09900 (6)	0.0217 (2)
H6B	0.7367	0.2511	0.0602	0.026*
H6C	0.6692	0.3872	0.0754	0.026*
C7	0.75666 (9)	0.47314 (12)	0.20190 (7)	0.0212 (2)
H7A	0.7753	0.4615	0.2562	0.025*
H7B	0.6804	0.4975	0.1970	0.025*
C4	0.92728 (10)	0.32834 (14)	0.42962 (7)	0.0270 (3)
H4B	0.9165	0.4130	0.4582	0.040*
H4C	0.9380	0.2512	0.4646	0.040*
H4D	0.8646	0.3107	0.3967	0.040*
C5	0.60582 (10)	0.21306 (14)	0.12663 (8)	0.0320 (3)
H5B	0.5577	0.1901	0.0839	0.048*
H5C	0.5668	0.2642	0.1643	0.048*
H5D	0.6344	0.1283	0.1492	0.048*
C8	0.82384 (11)	0.59180 (13)	0.16992 (8)	0.0321 (3)
H8A	0.8099	0.6767	0.1976	0.048*
H8B	0.8045	0.6050	0.1165	0.048*
H8C	0.8995	0.5687	0.1755	0.048*
C1	1.09742 (10)	0.01179 (12)	0.41592 (7)	0.0244 (2)
H1A	1.1571	−0.0478	0.4314	0.037*
H1B	1.0420	−0.0433	0.3901	0.037*
H1C	1.0684	0.0553	0.4605	0.037*
H13A	1.0787 (13)	−0.3377 (19)	−0.0021 (10)	0.043 (5)*
H13B	1.0561 (14)	−0.325 (2)	0.0845 (11)	0.050 (5)*
H13C	1.1172 (14)	−0.2076 (19)	0.0445 (10)	0.046 (5)*
H3A	1.0310 (12)	−0.1104 (16)	0.1438 (8)	0.027 (4)*

	U11	U22	U33	U12	U13	U23
N6	0.0158 (4)	0.0174 (4)	0.0152 (4)	0.0012 (3)	−0.0017 (3)	−0.0008 (3)
O2	0.0243 (4)	0.0356 (5)	0.0240 (4)	0.0003 (3)	−0.0093 (3)	0.0004 (4)
O1	0.0308 (4)	0.0284 (4)	0.0169 (4)	−0.0089 (3)	−0.0008 (3)	−0.0064 (3)
N3	0.0177 (4)	0.0185 (4)	0.0148 (4)	0.0038 (3)	−0.0056 (3)	−0.0029 (3)
N5	0.0152 (4)	0.0170 (4)	0.0157 (4)	0.0002 (3)	−0.0001 (3)	−0.0017 (3)
N4	0.0152 (4)	0.0170 (4)	0.0135 (4)	0.0000 (3)	−0.0011 (3)	−0.0009 (3)
N7	0.0160 (4)	0.0182 (4)	0.0143 (4)	0.0002 (3)	−0.0022 (3)	−0.0035 (3)
N2	0.0176 (4)	0.0173 (4)	0.0132 (4)	−0.0008 (3)	−0.0031 (3)	−0.0010 (3)
C19	0.0178 (5)	0.0198 (5)	0.0125 (5)	−0.0063 (4)	−0.0017 (4)	0.0007 (4)
N1	0.0208 (4)	0.0233 (5)	0.0156 (4)	−0.0085 (4)	−0.0025 (3)	0.0010 (4)
N8	0.0173 (4)	0.0187 (4)	0.0196 (4)	0.0037 (3)	−0.0027 (3)	−0.0018 (4)
C15	0.0192 (5)	0.0177 (5)	0.0171 (5)	0.0014 (4)	−0.0011 (4)	−0.0035 (4)
C11	0.0145 (4)	0.0161 (5)	0.0133 (5)	−0.0014 (4)	0.0004 (4)	0.0002 (4)
C16	0.0161 (5)	0.0149 (5)	0.0132 (5)	−0.0017 (4)	0.0000 (4)	0.0010 (4)
C17	0.0166 (5)	0.0161 (5)	0.0179 (5)	0.0003 (4)	0.0008 (4)	−0.0003 (4)
C10	0.0131 (4)	0.0173 (5)	0.0132 (5)	−0.0028 (4)	0.0017 (4)	0.0003 (4)
C18	0.0199 (5)	0.0166 (5)	0.0162 (5)	−0.0033 (4)	0.0024 (4)	−0.0037 (4)
C12	0.0164 (5)	0.0154 (5)	0.0134 (5)	0.0000 (4)	−0.0007 (4)	0.0009 (4)
C14	0.0173 (5)	0.0198 (5)	0.0190 (5)	0.0008 (4)	−0.0025 (4)	0.0005 (4)
C9	0.0141 (5)	0.0170 (5)	0.0150 (5)	−0.0009 (4)	0.0016 (4)	0.0013 (4)
C2	0.0148 (5)	0.0203 (5)	0.0150 (5)	−0.0008 (4)	−0.0027 (4)	−0.0009 (4)
C13	0.0232 (6)	0.0256 (6)	0.0185 (5)	0.0084 (4)	−0.0052 (4)	−0.0043 (4)
C3	0.0209 (5)	0.0204 (5)	0.0184 (5)	−0.0010 (4)	−0.0028 (4)	−0.0064 (4)
C6	0.0205 (5)	0.0249 (6)	0.0192 (5)	0.0062 (4)	−0.0054 (4)	−0.0004 (4)
C7	0.0197 (5)	0.0202 (5)	0.0237 (5)	0.0062 (4)	0.0011 (4)	−0.0026 (4)
C4	0.0279 (6)	0.0320 (6)	0.0213 (6)	0.0027 (5)	0.0039 (5)	−0.0068 (5)
C5	0.0251 (6)	0.0302 (7)	0.0398 (7)	−0.0021 (5)	−0.0131 (5)	0.0053 (5)
C8	0.0366 (7)	0.0212 (6)	0.0388 (7)	0.0008 (5)	0.0071 (6)	−0.0016 (5)
C1	0.0276 (6)	0.0234 (6)	0.0223 (5)	−0.0002 (4)	0.0028 (4)	0.0026 (4)

N6—C11	1.3294 (13)	C12—C13	1.5023 (14)
N6—C9	1.3502 (14)	C14—H14A	0.9300
O2—N1	1.2354 (13)	C2—C1	1.5182 (15)
O1—N1	1.2295 (13)	C2—H2B	0.9700
N3—N2	1.3562 (12)	C2—H2C	0.9700
N3—C11	1.3742 (14)	C13—H13A	0.958 (18)
N3—H3A	0.868 (15)	C13—H13B	0.96 (2)
N5—C10	1.3466 (13)	C13—H13C	0.986 (18)
N5—C9	1.3470 (14)	C3—C4	1.5285 (17)
N4—C11	1.3426 (13)	C3—H3D	0.9700
N4—C10	1.3490 (14)	C3—H3E	0.9700
N7—C10	1.3578 (13)	C6—C5	1.5170 (18)
N7—C2	1.4632 (13)	C6—H6B	0.9700
N7—C3	1.4641 (13)	C6—H6C	0.9700
N2—C12	1.2902 (14)	C7—C8	1.5195 (17)
C19—C18	1.3846 (15)	C7—H7A	0.9700
C19—C14	1.3876 (15)	C7—H7B	0.9700
C19—N1	1.4623 (13)	C4—H4B	0.9600
N8—C9	1.3549 (13)	C4—H4C	0.9600
N8—C7	1.4628 (14)	C4—H4D	0.9600
N8—C6	1.4639 (14)	C5—H5B	0.9600
C15—C14	1.3811 (15)	C5—H5C	0.9600
C15—C16	1.4072 (14)	C5—H5D	0.9600
C15—H15A	0.9300	C8—H8A	0.9600
C16—C17	1.4011 (14)	C8—H8B	0.9600
C16—C12	1.4860 (14)	C8—H8C	0.9600
C17—C18	1.3897 (15)	C1—H1A	0.9600
C17—H17A	0.9300	C1—H1B	0.9600
C18—H18A	0.9300	C1—H1C	0.9600
C11—N6—C9	112.92 (9)	C1—C2—H2C	108.9
N2—N3—C11	120.30 (9)	H2B—C2—H2C	107.7
N2—N3—H3A	123.2 (10)	C12—C13—H13A	115.6 (10)
C11—N3—H3A	116.5 (10)	C12—C13—H13B	112.8 (11)
C10—N5—C9	113.82 (9)	H13A—C13—H13B	108.0 (15)
C11—N4—C10	112.86 (9)	C12—C13—H13C	110.4 (10)
C10—N7—C2	120.71 (9)	H13A—C13—H13C	105.4 (14)
C10—N7—C3	120.12 (9)	H13B—C13—H13C	103.7 (15)
C2—N7—C3	119.08 (8)	N7—C3—C4	113.88 (9)
C12—N2—N3	117.98 (9)	N7—C3—H3D	108.8
C18—C19—C14	122.29 (9)	C4—C3—H3D	108.8
C18—C19—N1	119.22 (10)	N7—C3—H3E	108.8
C14—C19—N1	118.47 (10)	C4—C3—H3E	108.8
O1—N1—O2	122.83 (9)	H3D—C3—H3E	107.7
O1—N1—C19	118.75 (9)	N8—C6—C5	111.95 (10)
O2—N1—C19	118.42 (9)	N8—C6—H6B	109.2
C9—N8—C7	121.34 (9)	C5—C6—H6B	109.2
C9—N8—C6	120.77 (9)	N8—C6—H6C	109.2
C7—N8—C6	117.73 (9)	C5—C6—H6C	109.2
C14—C15—C16	121.06 (10)	H6B—C6—H6C	107.9
C14—C15—H15A	119.5	N8—C7—C8	111.88 (9)
C16—C15—H15A	119.5	N8—C7—H7A	109.2
N6—C11—N4	127.98 (10)	C8—C7—H7A	109.2
N6—C11—N3	118.56 (9)	N8—C7—H7B	109.2
N4—C11—N3	113.46 (9)	C8—C7—H7B	109.2
C17—C16—C15	118.28 (9)	H7A—C7—H7B	107.9
C17—C16—C12	122.27 (9)	C3—C4—H4B	109.5
C15—C16—C12	119.44 (9)	C3—C4—H4C	109.5
C18—C17—C16	121.36 (10)	H4B—C4—H4C	109.5
C18—C17—H17A	119.3	C3—C4—H4D	109.5
C16—C17—H17A	119.3	H4B—C4—H4D	109.5
N5—C10—N4	126.06 (9)	H4C—C4—H4D	109.5
N5—C10—N7	116.60 (9)	C6—C5—H5B	109.5
N4—C10—N7	117.34 (9)	C6—C5—H5C	109.5
C19—C18—C17	118.25 (10)	H5B—C5—H5C	109.5
C19—C18—H18A	120.9	C6—C5—H5D	109.5
C17—C18—H18A	120.9	H5B—C5—H5D	109.5
N2—C12—C16	114.46 (9)	H5C—C5—H5D	109.5
N2—C12—C13	123.85 (9)	C7—C8—H8A	109.5
C16—C12—C13	121.66 (9)	C7—C8—H8B	109.5
C15—C14—C19	118.74 (10)	H8A—C8—H8B	109.5
C15—C14—H14A	120.6	C7—C8—H8C	109.5
C19—C14—H14A	120.6	H8A—C8—H8C	109.5
N5—C9—N6	126.22 (9)	H8B—C8—H8C	109.5
N5—C9—N8	117.19 (9)	C2—C1—H1A	109.5
N6—C9—N8	116.59 (9)	C2—C1—H1B	109.5
N7—C2—C1	113.49 (9)	H1A—C1—H1B	109.5
N7—C2—H2B	108.9	C2—C1—H1C	109.5
C1—C2—H2B	108.9	H1A—C1—H1C	109.5
N7—C2—H2C	108.9	H1B—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.868 (15)	2.491 (15)	3.2751 (15)	150.7 (13)
N3—H3A···O2i	0.868 (15)	2.474 (15)	3.2486 (15)	149.0 (13)
C2—H2C···N4	0.97	2.38	2.7252 (15)	100
C7—H7A···N5	0.97	2.39	2.7322 (16)	100
C15—H15A···N2	0.93	2.39	2.7128 (15)	100
C1—H1A···Cg2ii	0.96	2.91	3.7486 (16)	147
C7—H7B···Cg1iii	0.97	2.71	3.3835 (15)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1i	0.868 (15)	2.491 (15)	3.2751 (15)	150.7 (13)
N3—H3A⋯O2i	0.868 (15)	2.474 (15)	3.2486 (15)	149.0 (13)
C2—H2C⋯N4	0.97	2.38	2.7252 (15)	100
C7—H7A⋯N5	0.97	2.39	2.7322 (16)	100
C15—H15A⋯N2	0.93	2.39	2.7128 (15)	100
C1—H1A⋯Cg2ii	0.96	2.91	3.7486 (16)	147
C7—H7B⋯Cg1iii	0.97	2.71	3.3835 (15)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the N4–N6/ C9–C11 and C14–C19 rings, respectively.