Ethyl 1-benzyl-5-{[(isopropyl-amino)(3-nitro-phen-oxy)methyl-idene]amino}-1H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(22)H(24)N(6)O(5), the triazole ring is essentially planar with a maximum deviation of 0.005 (2) Å and forms dihedral angles of 79.78 (11) and 86.22 (11)° with the phenyl and benzene rings, respectively. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N, C-H⋯O and C-H⋯π inter-actions into a three-dimensional network.

Related literature

For the biological activity of 8-aza­n class="Chemical">guanine derivatives, see: Roblin et al. (1945 ▶); Ding et al. (2004 ▶); Mitchell et al. (1950 ▶); Levine et al. (1963 ▶); Montgomery et al. (1962 ▶); Yamamoto et al. (1967 ▶); Bariana (1971 ▶); Holland et al. (1975 ▶). For related structures, see: Chen & Shi (2006 ▶); Ferguson et al. (1998 ▶); Li et al. (2004 ▶); Maldonado et al. (2006 ▶); Wang et al. (2006 ▶); Xiao & Shi (2007 ▶); Zeng et al. (2006 ▶, 2009 ▶); Zhao, Hu et al. (2005 ▶); Zhao, Wang & Ding (2005 ▶); Zhao, Xie et al. (2005 ▶).

Experimental

Crystal data

C22H24N6O5

M = 452.47

Monoclinic,

a = 11.5019 (7) Å

b = 14.5616 (9) Å

c = 14.1758 (9) Å

β = 106.384 (1)°

V = 2277.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.985, T max = 0.990

16973 measured reflections

5620 independent reflections

4276 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.170

S = 1.11

5620 reflections

304 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046659/rz2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046659/rz2518Isup2.hkl

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

C22H24N6O5	F(000) = 952
Mr = 452.47	Dx = 1.319 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4925 reflections
a = 11.5019 (7) Å	θ = 2.3–27.5°
b = 14.5616 (9) Å	µ = 0.10 mm−1
c = 14.1758 (9) Å	T = 298 K
β = 106.384 (1)°	Block, colourless
V = 2277.8 (2) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5620 independent reflections
Radiation source: fine-focus sealed tube	4276 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.985, Tmax = 0.990	k = −19→11
16973 measured reflections	l = −18→18

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.3769P] where P = (Fo2 + 2Fc2)/3
5620 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.83494 (16)	0.73129 (13)	0.46761 (13)	0.0443 (4)
C2	0.92546 (19)	0.79033 (16)	0.45953 (18)	0.0607 (6)
H2	0.9053	0.8448	0.4245	0.073*
C3	1.0448 (2)	0.7693 (2)	0.5027 (2)	0.0778 (8)
H3	1.1051	0.8096	0.4969	0.093*
C4	1.0756 (2)	0.6893 (3)	0.5545 (2)	0.0880 (10)
H4	1.1565	0.6761	0.5855	0.106*
C5	0.9865 (3)	0.6285 (2)	0.56061 (19)	0.0858 (9)
H5	1.0073	0.5731	0.5936	0.103*
C6	0.8662 (2)	0.64966 (17)	0.51778 (17)	0.0634 (6)
H6	0.8061	0.6088	0.5227	0.076*
C7	0.70362 (17)	0.75548 (14)	0.42216 (15)	0.0496 (5)
H7A	0.6892	0.7643	0.3520	0.060*
H7B	0.6531	0.7050	0.4318	0.060*
C8	0.67486 (14)	0.92697 (13)	0.43699 (12)	0.0386 (4)
C9	0.64906 (14)	0.97754 (13)	0.51172 (12)	0.0374 (4)
C10	0.65826 (15)	1.07626 (14)	0.52721 (13)	0.0428 (4)
C11	0.6438 (2)	1.19830 (17)	0.63312 (18)	0.0666 (6)
H11A	0.5876	1.2347	0.5832	0.080*
H11B	0.7256	1.2178	0.6369	0.080*
C12	0.6194 (3)	1.2108 (2)	0.7301 (2)	0.0843 (8)
H12A	0.5398	1.1884	0.7264	0.126*
H12B	0.6244	1.2749	0.7468	0.126*
H12C	0.6784	1.1773	0.7795	0.126*
C13	0.65271 (15)	1.00782 (13)	0.29254 (12)	0.0405 (4)
C14	0.48968 (17)	1.11872 (14)	0.21120 (13)	0.0473 (5)
H14	0.5274	1.1187	0.1572	0.057*
C15	0.35540 (19)	1.09763 (18)	0.16922 (17)	0.0655 (6)
H15A	0.3457	1.0371	0.1413	0.098*
H15B	0.3194	1.1417	0.1191	0.098*
H15C	0.3164	1.1008	0.2207	0.098*
C16	0.5115 (3)	1.21091 (17)	0.26153 (18)	0.0714 (7)
H16A	0.4759	1.2116	0.3152	0.107*
H16B	0.4754	1.2582	0.2153	0.107*
H16C	0.5971	1.2216	0.2861	0.107*
C17	0.82682 (16)	1.01845 (14)	0.23484 (13)	0.0435 (4)
C18	0.85824 (16)	0.97580 (13)	0.15946 (13)	0.0432 (4)
H18	0.7997	0.9553	0.1038	0.052*
C19	0.98042 (18)	0.96439 (14)	0.16946 (15)	0.0496 (5)
C20	1.06905 (19)	0.99366 (19)	0.25005 (19)	0.0682 (7)
H20	1.1505	0.9845	0.2549	0.082*
C21	1.0339 (2)	1.0371 (2)	0.32389 (19)	0.0785 (8)
H21	1.0926	1.0580	0.3792	0.094*
C22	0.9133 (2)	1.04989 (19)	0.31693 (16)	0.0652 (6)
H22	0.8903	1.0794	0.3670	0.078*
N1	0.66986 (13)	0.83894 (11)	0.46539 (11)	0.0430 (4)
N2	0.64102 (15)	0.83418 (12)	0.55231 (12)	0.0498 (4)
N3	0.62788 (13)	0.91804 (12)	0.57907 (11)	0.0447 (4)
N4	0.70987 (13)	0.94745 (12)	0.35461 (11)	0.0455 (4)
N5	0.54469 (13)	1.04458 (12)	0.28047 (11)	0.0439 (4)
H5A	0.5090 (19)	1.0317 (14)	0.3220 (16)	0.053*
N6	1.0155 (2)	0.91968 (15)	0.08856 (18)	0.0698 (6)
O1	0.69213 (14)	1.12893 (11)	0.47476 (11)	0.0593 (4)
O2	0.62878 (12)	1.10169 (9)	0.60849 (10)	0.0500 (3)
O3	0.70407 (11)	1.03569 (10)	0.22136 (9)	0.0528 (4)
O4	0.9375 (2)	0.89508 (16)	0.01765 (16)	0.1013 (7)
O5	1.1227 (2)	0.91031 (17)	0.09688 (19)	0.1151 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0471 (10)	0.0477 (11)	0.0431 (9)	0.0052 (8)	0.0210 (8)	−0.0076 (8)
C2	0.0551 (12)	0.0505 (13)	0.0834 (15)	0.0011 (10)	0.0306 (11)	−0.0126 (11)
C3	0.0489 (12)	0.0810 (19)	0.108 (2)	−0.0053 (12)	0.0295 (13)	−0.0411 (17)
C4	0.0548 (14)	0.125 (3)	0.0771 (17)	0.0327 (17)	0.0069 (12)	−0.0258 (18)
C5	0.088 (2)	0.101 (2)	0.0679 (16)	0.0427 (18)	0.0212 (14)	0.0184 (15)
C6	0.0686 (14)	0.0688 (16)	0.0606 (13)	0.0095 (12)	0.0308 (11)	0.0101 (11)
C7	0.0496 (10)	0.0482 (12)	0.0541 (11)	0.0008 (9)	0.0196 (9)	−0.0052 (9)
C8	0.0280 (7)	0.0500 (11)	0.0404 (9)	0.0051 (7)	0.0140 (6)	0.0050 (8)
C9	0.0305 (7)	0.0485 (11)	0.0368 (8)	−0.0005 (7)	0.0152 (6)	0.0024 (8)
C10	0.0324 (8)	0.0556 (12)	0.0417 (9)	−0.0059 (8)	0.0126 (7)	−0.0004 (9)
C11	0.0732 (15)	0.0536 (14)	0.0767 (15)	−0.0157 (11)	0.0271 (12)	−0.0179 (12)
C12	0.098 (2)	0.0805 (19)	0.0757 (17)	0.0005 (15)	0.0265 (14)	−0.0294 (15)
C13	0.0398 (9)	0.0514 (11)	0.0351 (8)	0.0012 (8)	0.0184 (7)	0.0005 (8)
C14	0.0497 (10)	0.0560 (12)	0.0424 (9)	0.0108 (9)	0.0232 (8)	0.0099 (9)
C15	0.0512 (12)	0.0804 (17)	0.0640 (13)	0.0159 (11)	0.0150 (10)	0.0107 (12)
C16	0.0987 (18)	0.0556 (14)	0.0640 (14)	0.0020 (13)	0.0295 (13)	0.0087 (12)
C17	0.0412 (9)	0.0518 (11)	0.0438 (9)	0.0010 (8)	0.0222 (7)	0.0068 (8)
C18	0.0454 (9)	0.0456 (11)	0.0429 (9)	−0.0027 (8)	0.0197 (8)	0.0027 (8)
C19	0.0514 (11)	0.0474 (12)	0.0607 (12)	0.0034 (9)	0.0334 (9)	0.0061 (9)
C20	0.0402 (10)	0.0885 (18)	0.0812 (16)	−0.0018 (11)	0.0255 (11)	0.0057 (14)
C21	0.0529 (13)	0.112 (2)	0.0677 (15)	−0.0206 (13)	0.0130 (11)	−0.0204 (15)
C22	0.0605 (13)	0.0871 (18)	0.0546 (12)	−0.0113 (12)	0.0270 (10)	−0.0182 (12)
N1	0.0407 (8)	0.0483 (10)	0.0453 (8)	0.0047 (7)	0.0209 (6)	0.0040 (7)
N2	0.0539 (9)	0.0551 (11)	0.0489 (9)	0.0017 (8)	0.0280 (7)	0.0075 (8)
N3	0.0471 (8)	0.0511 (10)	0.0423 (8)	0.0000 (7)	0.0228 (7)	0.0038 (7)
N4	0.0443 (8)	0.0578 (10)	0.0419 (8)	0.0127 (7)	0.0242 (6)	0.0081 (7)
N5	0.0410 (8)	0.0572 (10)	0.0401 (8)	0.0081 (7)	0.0224 (6)	0.0109 (7)
N6	0.0799 (14)	0.0630 (13)	0.0853 (15)	0.0147 (11)	0.0538 (12)	0.0007 (11)
O1	0.0667 (9)	0.0590 (9)	0.0594 (8)	−0.0195 (7)	0.0296 (7)	0.0017 (7)
O2	0.0562 (8)	0.0491 (8)	0.0505 (7)	−0.0073 (6)	0.0244 (6)	−0.0071 (6)
O3	0.0456 (7)	0.0770 (10)	0.0447 (7)	0.0127 (7)	0.0271 (6)	0.0163 (7)
O4	0.1143 (17)	0.1171 (18)	0.0855 (13)	0.0095 (13)	0.0492 (13)	−0.0371 (13)
O5	0.0924 (14)	0.129 (2)	0.156 (2)	0.0250 (13)	0.0866 (15)	−0.0155 (16)

C1—C2	1.380 (3)	C13—N5	1.319 (2)
C1—C6	1.380 (3)	C13—O3	1.367 (2)
C1—C7	1.507 (3)	C14—N5	1.476 (2)
C2—C3	1.371 (3)	C14—C16	1.508 (3)
C2—H2	0.9300	C14—C15	1.522 (3)
C3—C4	1.370 (4)	C14—H14	0.9800
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.375 (5)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.379 (4)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—N1	1.462 (2)	C17—C18	1.370 (3)
C7—H7A	0.9700	C17—C22	1.378 (3)
C7—H7B	0.9700	C17—O3	1.393 (2)
C8—N1	1.350 (2)	C18—C19	1.382 (3)
C8—N4	1.371 (2)	C18—H18	0.9300
C8—C9	1.389 (2)	C19—C20	1.367 (3)
C9—N3	1.361 (2)	C19—N6	1.471 (3)
C9—C10	1.454 (3)	C20—C21	1.377 (3)
C10—O1	1.207 (2)	C20—H20	0.9300
C10—O2	1.342 (2)	C21—C22	1.376 (3)
C11—O2	1.448 (3)	C21—H21	0.9300
C11—C12	1.489 (3)	C22—H22	0.9300
C11—H11A	0.9700	N1—N2	1.365 (2)
C11—H11B	0.9700	N2—N3	1.300 (2)
C12—H12A	0.9600	N5—H5A	0.83 (2)
C12—H12B	0.9600	N6—O4	1.198 (3)
C12—H12C	0.9600	N6—O5	1.212 (3)
C13—N4	1.286 (2)
C2—C1—C6	119.1 (2)	N5—C14—C15	108.05 (16)
C2—C1—C7	120.50 (19)	C16—C14—C15	112.33 (19)
C6—C1—C7	120.38 (19)	N5—C14—H14	108.6
C3—C2—C1	120.5 (2)	C16—C14—H14	108.6
C3—C2—H2	119.7	C15—C14—H14	108.6
C1—C2—H2	119.7	C14—C15—H15A	109.5
C4—C3—C2	120.3 (3)	C14—C15—H15B	109.5
C4—C3—H3	119.9	H15A—C15—H15B	109.5
C2—C3—H3	119.9	C14—C15—H15C	109.5
C3—C4—C5	119.8 (2)	H15A—C15—H15C	109.5
C3—C4—H4	120.1	H15B—C15—H15C	109.5
C5—C4—H4	120.1	C14—C16—H16A	109.5
C4—C5—C6	120.1 (3)	C14—C16—H16B	109.5
C4—C5—H5	120.0	H16A—C16—H16B	109.5
C6—C5—H5	120.0	C14—C16—H16C	109.5
C5—C6—C1	120.2 (2)	H16A—C16—H16C	109.5
C5—C6—H6	119.9	H16B—C16—H16C	109.5
C1—C6—H6	119.9	C18—C17—C22	121.54 (18)
N1—C7—C1	111.57 (16)	C18—C17—O3	117.06 (16)
N1—C7—H7A	109.3	C22—C17—O3	121.18 (17)
C1—C7—H7A	109.3	C17—C18—C19	117.32 (18)
N1—C7—H7B	109.3	C17—C18—H18	121.3
C1—C7—H7B	109.3	C19—C18—H18	121.3
H7A—C7—H7B	108.0	C20—C19—C18	123.04 (19)
N1—C8—N4	120.53 (16)	C20—C19—N6	119.04 (19)
N1—C8—C9	103.88 (14)	C18—C19—N6	117.92 (19)
N4—C8—C9	135.35 (18)	C19—C20—C21	117.96 (19)
N3—C9—C8	108.45 (16)	C19—C20—H20	121.0
N3—C9—C10	122.91 (15)	C21—C20—H20	121.0
C8—C9—C10	128.12 (16)	C22—C21—C20	120.9 (2)
O1—C10—O2	123.88 (19)	C22—C21—H21	119.5
O1—C10—C9	123.91 (17)	C20—C21—H21	119.5
O2—C10—C9	112.17 (15)	C21—C22—C17	119.2 (2)
O2—C11—C12	107.5 (2)	C21—C22—H22	120.4
O2—C11—H11A	110.2	C17—C22—H22	120.4
C12—C11—H11A	110.2	C8—N1—N2	111.03 (15)
O2—C11—H11B	110.2	C8—N1—C7	128.74 (15)
C12—C11—H11B	110.2	N2—N1—C7	119.81 (16)
H11A—C11—H11B	108.5	N3—N2—N1	107.07 (15)
C11—C12—H12A	109.5	N2—N3—C9	109.55 (14)
C11—C12—H12B	109.5	C13—N4—C8	121.01 (14)
H12A—C12—H12B	109.5	C13—N5—C14	126.48 (15)
C11—C12—H12C	109.5	C13—N5—H5A	117.0 (15)
H12A—C12—H12C	109.5	C14—N5—H5A	115.6 (15)
H12B—C12—H12C	109.5	O4—N6—O5	123.3 (2)
N4—C13—N5	130.36 (16)	O4—N6—C19	118.8 (2)
N4—C13—O3	117.65 (15)	O5—N6—C19	118.0 (2)
N5—C13—O3	111.79 (15)	C10—O2—C11	115.68 (16)
N5—C14—C16	110.70 (16)	C13—O3—C17	118.53 (14)
C6—C1—C2—C3	−1.6 (3)	C9—C8—N1—N2	0.76 (18)
C7—C1—C2—C3	178.52 (19)	N4—C8—N1—C7	3.4 (3)
C1—C2—C3—C4	0.0 (4)	C9—C8—N1—C7	−171.70 (16)
C2—C3—C4—C5	2.0 (4)	C1—C7—N1—C8	89.8 (2)
C3—C4—C5—C6	−2.4 (4)	C1—C7—N1—N2	−82.1 (2)
C4—C5—C6—C1	0.8 (4)	C8—N1—N2—N3	−0.05 (19)
C2—C1—C6—C5	1.1 (3)	C7—N1—N2—N3	173.18 (15)
C7—C1—C6—C5	−179.0 (2)	N1—N2—N3—C9	−0.72 (19)
C2—C1—C7—N1	−62.2 (2)	C8—C9—N3—N2	1.21 (19)
C6—C1—C7—N1	117.9 (2)	C10—C9—N3—N2	−171.13 (16)
N1—C8—C9—N3	−1.17 (17)	N5—C13—N4—C8	−16.3 (3)
N4—C8—C9—N3	−175.21 (18)	O3—C13—N4—C8	169.37 (17)
N1—C8—C9—C10	170.66 (17)	N1—C8—N4—C13	136.47 (19)
N4—C8—C9—C10	−3.4 (3)	C9—C8—N4—C13	−50.3 (3)
N3—C9—C10—O1	170.10 (17)	N4—C13—N5—C14	175.4 (2)
C8—C9—C10—O1	−0.7 (3)	O3—C13—N5—C14	−10.0 (3)
N3—C9—C10—O2	−7.7 (2)	C16—C14—N5—C13	−94.9 (2)
C8—C9—C10—O2	−178.49 (15)	C15—C14—N5—C13	141.7 (2)
C22—C17—C18—C19	0.8 (3)	C20—C19—N6—O4	−179.2 (2)
O3—C17—C18—C19	175.51 (16)	C18—C19—N6—O4	0.0 (3)
C17—C18—C19—C20	−0.1 (3)	C20—C19—N6—O5	0.2 (3)
C17—C18—C19—N6	−179.29 (18)	C18—C19—N6—O5	179.4 (2)
C18—C19—C20—C21	−0.5 (4)	O1—C10—O2—C11	−2.0 (3)
N6—C19—C20—C21	178.6 (2)	C9—C10—O2—C11	175.81 (16)
C19—C20—C21—C22	0.5 (4)	C12—C11—O2—C10	−174.08 (18)
C20—C21—C22—C17	0.2 (4)	N4—C13—O3—C17	−17.6 (3)
C18—C17—C22—C21	−0.8 (4)	N5—C13—O3—C17	166.98 (17)
O3—C17—C22—C21	−175.3 (2)	C18—C17—O3—C13	128.60 (19)
N4—C8—N1—N2	175.89 (14)	C22—C17—O3—C13	−56.7 (3)

Cg1 and Cg2 are the centroids of the triazole and C1–C6 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N3i	0.83 (2)	2.50 (2)	3.230 (2)	148 (2)
C3—H3···O1ii	0.93	2.42	3.303 (3)	158
C21—H21···Cg1ii	0.93	2.98	3.829 (3)	153
C14—H14···Cg2iii	0.98	2.78	3.625 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the triazole and C1–C6 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯N3i	0.83 (2)	2.50 (2)	3.230 (2)	148 (2)
C3—H3⋯O1ii	0.93	2.42	3.303 (3)	158
C21—H21⋯Cg1ii	0.93	2.98	3.829 (3)	153
C14—H14⋯Cg2iii	0.98	2.78	3.625 (2)	145

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