Ethyl 1-benzyl-5-{[(isopropyl­amino)(3-nitro­phen­oxy)methyl­idene]amino}-1H-1,2,3-triazole-4-carboxyl­ate

Wang, H.-M.; Deng, S.-H.; Zeng, X.-H.; Chen, P.; Cao, F.-J.

doi:10.1107/S1600536810046659

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3207-o3208

https://doi.org/10.1107/S1600536810046659

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Ethyl 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}-1H-1,2,3-triazole-4-carboxylate

Hong-Mei Wang,^a Shou-Heng Deng,^b Xiao-Hua Zeng,^a ^* Ping Chen ^b and Feng-Jun Cao ^b

^aInstitute of Medicinal Chemistry, Hubei Medical University, Shiyan 442000, People's Republic of China, and ^bCenter of Oncology, People's Hospital affiliated with Hubei Medical University, Shi Yan 442000, People's Republic of China
^*Correspondence e-mail: zengken@126.com

(Received 1 November 2010; accepted 11 November 2010; online 17 November 2010)

In the title compound, C₂₂H₂₄N₆O₅, 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, molecules are linked by intermolecular N—H⋯N, C—H⋯O and C—H⋯π interactions into a three-dimensional network.

Related literature

For the biological activity of 8-azaguanine 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_r = 452.47
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.170
S = 1.11
5620 reflections
304 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046659/rz2518Isup2.hkl

checkCIF report

Comment top

The derivatives of heterocycles containing 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (Roblin et al., 1945; Ding et al., 2004), encephaloma cell inhibitor activity (Mitchell et al., 1950; Levine et al., 1963), antileukemie activity (Montgomery et al., 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975). In recent years, our group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of beta-ethoxycarbonyl iminophosphorane with aromatic isocyanate (Zhao, Xie et al., 2005). As a continuation of our research for new biologically active heterocycles, the title compound was obtained as an intermediate product from β-ethoxycarbonyl iminophosphorane with an alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazole ring are in good agreement with those observed for closely related structures (Zhao, Hu et al., 2005; Zhao, Wang & Ding, 2005). As reported for related compounds (Ferguson et al., 1998; Li et al., 2004; Maldonado et al., 2006; Zeng et al., 2006, 2009; Wang et al., 2006; Xiao & Shi, 2007; Chen & Shi, 2006), the triazole ring system is essentially planar, with a maximum displacement of 0.005 (2) Å for atom N3, and forms dihedral angles of 79.78 (11) and 86.22 (11)° with the phenyl and benzene rings, respectively. In the crystal packing, molecules are linked by intermolecular N—H···N, C—H···O and C—H···π hydrogen bonding interactions (Table 1) in a three-dimensional network.

Related literature top

For the biological activity of 8-azaguanine 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 top

To a solution of carbodiimide prepared according to Wang et al. (2006) in a mixed solvent (CH₂Cl₂/CH₃CN, 1:4 v/v, 15 ml) was added 3-nitrobenzene (3 mmol), and the reaction mixture was stirred for 6 h. The solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound in 92% yield (m.p. 437 K). Elemental analysis: calculated for C₂₂H₂₄N₆O₅: C, 58.40; H, 5.35; N, 18.57%. Found: C, 58.08; H, 5.49; N, 18.29%. Crystals suitable for X-ray diffraction study were obtained by recrystallization from EtOH and dichloromethane (1:3 v/v) at room temperature.

Structure description top

For the biological activity of 8-azaguanine 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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

Fig. 1. View of the molecule of showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.

Ethyl 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}- 1H-1,2,3-triazole-4-carboxylate top

Crystal data top

C₂₂H₂₄N₆O₅	F(000) = 952
M_r = 452.47	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0702P)² + 0.3769P] where P = (F_o² + 2F_c²)/3
5620 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₂₄N₆O₅	V = 2277.8 (2) Å³
M_r = 452.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5019 (7) Å	µ = 0.10 mm⁻¹
b = 14.5616 (9) Å	T = 298 K
c = 14.1758 (9) Å	0.16 × 0.12 × 0.10 mm
β = 106.384 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5620 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4276 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.990	R_int = 0.069
16973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.25 e Å⁻³
5620 reflections	Δρ_min = −0.19 e Å⁻³
304 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₆O₅
M_r	452.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.5019 (7), 14.5616 (9), 14.1758 (9)
β (°)	106.384 (1)
V (Å³)	2277.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.985, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	16973, 5620, 4276
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.170, 1.11
No. of reflections	5620
No. of parameters	304
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	157.7
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) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province of China (grant No. B200624004, B20092412) and the Shiyan Municipal Science and Technology Bureau (grant No. 20061835).

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Volume 66| Part 12| December 2010| Pages o3207-o3208

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-benzyl-5-{[(iso­propyl­amino)(3-nitro­phen­­oxy)methyl­­idene]amino}-1H-1,2,3-triazole-4-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1-benzyl-5-{[(isopropylamino)(3-nitrophenoxy)methylidene]amino}-1H-1,2,3-triazole-4-carboxylate