(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxy­but-2-en-1-one

Li, J.-M.; Yong, J.-P.

doi:10.1107/S1600536809050442

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o13

doi:10.1107/S1600536809050442

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(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxybut-2-en-1-one

Jiu-Ming Li ^a ^* and Jian-Ping Yong ^b

^aCollege of Chemistry, Inner Mongolia University for Nationalities, Tongliao 028043, People's Republic of China, and ^bSchool of Public Health, Ningxia Medical University, Yinchuan 750004, People's Republic of China
^*Correspondence e-mail: lijiuming10@yahoo.cn

(Received 19 November 2009; accepted 23 November 2009; online 4 December 2009)

The title compound, C₁₁H₁₁N₃O₃, crystallizes with two independent molecules of similar geometry in the asymmetric unit. The molecular conformations are stabilized by intramolecular C—H⋯O hydrogen bonds. The crystal packing consists of wave-like layers parallel to the bc plane formed by intermolecular C—H⋯O hydrogen-bonding interactions involving only one independent molecule.

Related literature

For related structures, see: Barlos et al. (1985 ); Singh et al. (1988 ). For details of the biological activity of benzentriazol-containing compounds, see: Zhang et al. (2002 ). For comparative bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₁N₃O₃
M_r = 233.23
Monoclinic, P 2₁ /c
a = 14.011 (3) Å
b = 10.014 (2) Å
c = 15.699 (3) Å
β = 100.13 (3)°
V = 2168.3 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.959, T_max = 0.969
15367 measured reflections
3771 independent reflections
3564 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.141
S = 1.17
3771 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2	0.95	2.45	2.925 (3)	111
C13—H13A⋯O5	0.95	2.49	2.961 (3)	111
C14—H14A⋯O4ⁱ	0.95	2.57	3.398 (3)	147
C16—H16A⋯O4ⁱⁱ	0.95	2.45	3.379 (3)	165
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y-1, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050442/rz2397sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050442/rz2397Isup2.hkl

checkCIF report

Comment top

Benzotriazole derivatives exhibit good pharmacological activities and a wide spectrum of biological activities (Zhang et al., 2002). In order to search for new benzotriazole compounds with higher bioactivity, we synthesized the title compound and describe its structure here.

The asymmetric unit of the title compound (Fig. 1) contains two independent molecules of similar geometry. The molecules are almost planar, the maximum deviation being 0.110 (2) Å for atom O2 in one molecule and 0.093 (3) Å for atom C22 in the other molecule. All bond lengths in the molecules are normal (Allen et al., 1987) and in a good agreement with those reported previously for related compound (Barlos et al., 1985; Singh et al., 1988). The molecular conformations are stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal packing, molecules containing the N4–N6 nitrogen atoms are linked by intermolecular C—H···O hydrogen bonds to form wavy layers parallel to the bc plane intersecting each other.

Related literature top

For related structures, see: Barlos et al. (1985); Singh et al. (1988). For details of the biological activity of benzentriazole-containing compounds, see: Zhang et al. (2002). For comparative bond lengths, see: Allen et al. (1987).

Experimental top

3-Methoxycrotonic acid (20 mmol) was dissolved in dichloromethane and cooled to 273 K, then 1-hydroxybenzotriazole (30 mmol) was added in one portion. After 10 h stirring at room temperature, the solution was washed successively with 1 N HCl and saturated NaCl, and the organic layer was separated, dried with Na₂SO₄ and evaporated to obtain the primary product. The pure compound was isolated by column chromatography (3.4 g, yield 73%). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethyl acetate solution at room temperature. ¹H NMR (400 MHz, CDCl3) δ: 8.49 (d, J = 8 Hz, 1H), 7.99 (d, J = 8 Hz, 1H), 7.75 (t, 1H), 7.53 (t, 1H), 6.30 (s, 1H), 3.85 (s, 3H), 2.50 (s, 3H).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom-labelling scheme and 40% probability displacement ellipsoids.

(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxybut-2-en-1-one top

Crystal data top

C₁₁H₁₁N₃O₃	F(000) = 976
M_r = 233.23	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6607 reflections
a = 14.011 (3) Å	θ = 1.3–27.5°
b = 10.014 (2) Å	µ = 0.11 mm⁻¹
c = 15.699 (3) Å	T = 173 K
β = 100.13 (3)°	Block, colourless
V = 2168.3 (8) Å³	0.40 × 0.40 × 0.30 mm
Z = 8

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3771 independent reflections
Radiation source: Sealed Tube	3564 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −11→16
T_min = 0.959, T_max = 0.969	k = −11→11
15367 measured reflections	l = −18→18

Refinement top

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.047P)² + 1.4328P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
3771 reflections	Δρ_max = 0.36 e Å⁻³
308 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (7)

Crystal data top

C₁₁H₁₁N₃O₃	V = 2168.3 (8) Å³
M_r = 233.23	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.011 (3) Å	µ = 0.11 mm⁻¹
b = 10.014 (2) Å	T = 173 K
c = 15.699 (3) Å	0.40 × 0.40 × 0.30 mm
β = 100.13 (3)°

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3771 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3564 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.969	R_int = 0.050
15367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.17	Δρ_max = 0.36 e Å⁻³
3771 reflections	Δρ_min = −0.28 e Å⁻³
308 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
O1	0.05575 (14)	1.36306 (16)	−0.08605 (11)	0.0400 (5)
O2	0.14314 (14)	0.85371 (17)	0.05299 (11)	0.0411 (5)
O3	0.18500 (13)	0.72121 (18)	−0.19749 (12)	0.0436 (5)
O4	0.45305 (13)	−0.36283 (16)	−0.08904 (11)	0.0387 (4)
O5	0.33528 (13)	0.14842 (17)	−0.00327 (10)	0.0383 (4)
O6	0.32908 (13)	0.26568 (17)	−0.26560 (11)	0.0380 (4)
N1	0.07616 (14)	1.25933 (19)	−0.03951 (12)	0.0297 (5)
N2	0.09586 (14)	1.14406 (18)	−0.07177 (12)	0.0292 (4)
N3	0.11216 (14)	1.05828 (19)	−0.00260 (11)	0.0272 (4)
N4	0.43065 (14)	−0.25590 (19)	−0.05301 (12)	0.0282 (4)
N5	0.40993 (14)	−0.14465 (19)	−0.09592 (12)	0.0286 (4)
N6	0.38814 (13)	−0.05422 (19)	−0.03598 (11)	0.0264 (4)
C1	0.10201 (16)	1.1226 (2)	0.07363 (14)	0.0278 (5)
C2	0.10832 (17)	1.0824 (3)	0.15936 (15)	0.0341 (6)
H2B	0.1237	0.9932	0.1773	0.041*
C3	0.09079 (18)	1.1801 (3)	0.21672 (15)	0.0375 (6)
H3A	0.0940	1.1566	0.2758	0.045*
C4	0.06852 (18)	1.3119 (3)	0.19175 (16)	0.0377 (6)
H4A	0.0574	1.3748	0.2343	0.045*
C5	0.06218 (17)	1.3534 (2)	0.10725 (16)	0.0337 (6)
H5B	0.0473	1.4428	0.0895	0.040*
C6	0.07931 (16)	1.2541 (2)	0.05007 (14)	0.0280 (5)
C7	0.13675 (16)	0.9212 (2)	−0.01186 (15)	0.0286 (5)
C8	0.15008 (16)	0.8828 (2)	−0.09752 (15)	0.0302 (5)
H8A	0.1417	0.9484	−0.1419	0.036*
C9	0.17412 (17)	0.7568 (2)	−0.11732 (16)	0.0336 (6)
C10	0.1935 (2)	0.6417 (3)	−0.0578 (2)	0.0485 (7)
H10A	0.2091	0.5631	−0.0900	0.073*
H10B	0.1358	0.6232	−0.0323	0.073*
H10C	0.2482	0.6625	−0.0118	0.073*
C11	0.1690 (2)	0.8191 (3)	−0.26569 (18)	0.0473 (7)
H11A	0.1797	0.7781	−0.3199	0.071*
H11B	0.2143	0.8937	−0.2509	0.071*
H11C	0.1023	0.8522	−0.2726	0.071*
C12	0.39549 (16)	−0.1127 (2)	0.04485 (14)	0.0271 (5)
C13	0.38077 (17)	−0.0679 (3)	0.12604 (15)	0.0326 (6)
H13A	0.3613	0.0211	0.1350	0.039*
C14	0.39604 (18)	−0.1599 (3)	0.19193 (16)	0.0368 (6)
H14A	0.3867	−0.1329	0.2479	0.044*
C15	0.42483 (18)	−0.2921 (3)	0.18018 (16)	0.0367 (6)
H15A	0.4350	−0.3513	0.2282	0.044*
C16	0.43866 (17)	−0.3378 (2)	0.10031 (15)	0.0333 (6)
H16A	0.4572	−0.4271	0.0911	0.040*
C17	0.42345 (16)	−0.2437 (2)	0.03457 (14)	0.0273 (5)
C18	0.35556 (16)	0.0780 (2)	−0.06071 (15)	0.0293 (5)
C19	0.35254 (16)	0.1095 (2)	−0.15081 (15)	0.0289 (5)
H19A	0.3658	0.0412	−0.1891	0.035*
C20	0.33127 (17)	0.2343 (2)	−0.18219 (15)	0.0307 (5)
C21	0.3085 (2)	0.3529 (2)	−0.13222 (18)	0.0404 (6)
H21A	0.2960	0.4300	−0.1710	0.061*
H21B	0.3637	0.3723	−0.0862	0.061*
H21C	0.2510	0.3344	−0.1066	0.061*
C22	0.3452 (2)	0.1631 (3)	−0.32498 (16)	0.0415 (6)
H22A	0.3413	0.2015	−0.3829	0.062*
H22B	0.2957	0.0936	−0.3265	0.062*
H22C	0.4096	0.1240	−0.3062	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0628 (12)	0.0248 (9)	0.0349 (9)	0.0044 (8)	0.0158 (9)	0.0052 (8)
O2	0.0557 (12)	0.0323 (10)	0.0359 (10)	0.0058 (8)	0.0098 (8)	0.0062 (8)
O3	0.0470 (11)	0.0364 (10)	0.0493 (11)	−0.0006 (8)	0.0138 (9)	−0.0164 (9)
O4	0.0562 (11)	0.0268 (9)	0.0349 (9)	0.0079 (8)	0.0128 (8)	−0.0030 (7)
O5	0.0519 (11)	0.0336 (9)	0.0302 (9)	0.0057 (8)	0.0090 (8)	−0.0069 (8)
O6	0.0448 (10)	0.0327 (10)	0.0388 (10)	0.0074 (8)	0.0132 (8)	0.0094 (8)
N1	0.0380 (11)	0.0234 (10)	0.0289 (10)	−0.0006 (8)	0.0090 (9)	−0.0008 (8)
N2	0.0380 (11)	0.0235 (10)	0.0266 (10)	−0.0004 (8)	0.0075 (8)	0.0001 (8)
N3	0.0335 (11)	0.0257 (10)	0.0231 (9)	0.0003 (8)	0.0066 (8)	0.0001 (8)
N4	0.0330 (11)	0.0247 (10)	0.0279 (10)	0.0001 (8)	0.0082 (8)	0.0003 (8)
N5	0.0352 (11)	0.0260 (10)	0.0255 (10)	0.0011 (8)	0.0078 (8)	−0.0011 (8)
N6	0.0306 (10)	0.0257 (10)	0.0232 (9)	−0.0003 (8)	0.0054 (8)	−0.0001 (8)
C1	0.0260 (12)	0.0314 (13)	0.0264 (12)	−0.0019 (10)	0.0057 (9)	−0.0021 (10)
C2	0.0334 (13)	0.0417 (14)	0.0271 (12)	0.0033 (11)	0.0050 (10)	0.0032 (11)
C3	0.0367 (14)	0.0526 (16)	0.0235 (12)	−0.0021 (12)	0.0063 (10)	−0.0025 (11)
C4	0.0358 (13)	0.0477 (16)	0.0301 (13)	−0.0028 (12)	0.0073 (11)	−0.0125 (12)
C5	0.0331 (13)	0.0307 (13)	0.0376 (13)	−0.0031 (10)	0.0068 (11)	−0.0073 (11)
C6	0.0310 (12)	0.0288 (12)	0.0246 (11)	−0.0039 (10)	0.0056 (10)	−0.0026 (10)
C7	0.0272 (12)	0.0248 (12)	0.0341 (13)	−0.0010 (9)	0.0066 (10)	0.0006 (10)
C8	0.0305 (12)	0.0269 (12)	0.0334 (13)	−0.0014 (10)	0.0064 (10)	−0.0017 (10)
C9	0.0276 (12)	0.0302 (13)	0.0433 (14)	−0.0027 (10)	0.0073 (11)	−0.0075 (11)
C10	0.0504 (17)	0.0285 (14)	0.0657 (19)	0.0052 (12)	0.0080 (15)	−0.0031 (13)
C11	0.0534 (17)	0.0480 (17)	0.0427 (15)	−0.0070 (14)	0.0149 (13)	−0.0159 (13)
C12	0.0250 (11)	0.0314 (13)	0.0243 (11)	−0.0047 (9)	0.0029 (9)	0.0002 (10)
C13	0.0374 (13)	0.0348 (13)	0.0265 (12)	−0.0012 (11)	0.0085 (10)	−0.0040 (10)
C14	0.0387 (14)	0.0459 (15)	0.0267 (12)	−0.0043 (12)	0.0084 (11)	−0.0023 (11)
C15	0.0402 (14)	0.0419 (15)	0.0285 (12)	−0.0060 (12)	0.0073 (11)	0.0068 (11)
C16	0.0334 (13)	0.0321 (13)	0.0343 (13)	−0.0046 (10)	0.0060 (11)	0.0032 (11)
C17	0.0290 (12)	0.0296 (12)	0.0235 (11)	−0.0043 (9)	0.0049 (9)	−0.0016 (9)
C18	0.0281 (12)	0.0259 (12)	0.0332 (13)	−0.0009 (9)	0.0035 (10)	−0.0028 (10)
C19	0.0313 (12)	0.0269 (12)	0.0285 (12)	−0.0010 (10)	0.0047 (10)	−0.0013 (10)
C20	0.0277 (12)	0.0312 (13)	0.0344 (13)	0.0002 (10)	0.0085 (10)	0.0023 (10)
C21	0.0433 (15)	0.0274 (13)	0.0523 (16)	0.0035 (11)	0.0131 (13)	0.0013 (12)
C22	0.0553 (17)	0.0390 (15)	0.0317 (13)	0.0053 (12)	0.0118 (12)	0.0062 (11)

Geometric parameters (Å, º) top

O1—N1	1.273 (2)	C8—C9	1.356 (3)
O2—C7	1.212 (3)	C8—H8A	0.9500
O3—C9	1.342 (3)	C9—C10	1.478 (4)
O3—C11	1.440 (3)	C10—H10A	0.9800
O4—N4	1.276 (2)	C10—H10B	0.9800
O5—C18	1.217 (3)	C10—H10C	0.9800
O6—C20	1.342 (3)	C11—H11A	0.9800
O6—C22	1.431 (3)	C11—H11B	0.9800
N1—N2	1.309 (3)	C11—H11C	0.9800
N1—C6	1.400 (3)	C12—C17	1.386 (3)
N2—N3	1.372 (3)	C12—C13	1.400 (3)
N3—C1	1.388 (3)	C13—C14	1.373 (3)
N3—C7	1.429 (3)	C13—H13A	0.9500
N4—N5	1.308 (3)	C14—C15	1.406 (4)
N4—C17	1.401 (3)	C14—H14A	0.9500
N5—N6	1.378 (3)	C15—C16	1.380 (3)
N6—C12	1.385 (3)	C15—H15A	0.9500
N6—C18	1.432 (3)	C16—C17	1.385 (3)
C1—C6	1.389 (3)	C16—H16A	0.9500
C1—C2	1.393 (3)	C18—C19	1.442 (3)
C2—C3	1.381 (4)	C19—C20	1.357 (3)
C2—H2B	0.9500	C19—H19A	0.9500
C3—C4	1.396 (4)	C20—C21	1.488 (3)
C3—H3A	0.9500	C21—H21A	0.9800
C4—C5	1.378 (4)	C21—H21B	0.9800
C4—H4A	0.9500	C21—H21C	0.9800
C5—C6	1.389 (3)	C22—H22A	0.9800
C5—H5B	0.9500	C22—H22B	0.9800
C7—C8	1.442 (3)	C22—H22C	0.9800

C9—O3—C11	119.2 (2)	H10A—C10—H10C	109.5
C20—O6—C22	119.25 (19)	H10B—C10—H10C	109.5
O1—N1—N2	122.60 (18)	O3—C11—H11A	109.5
O1—N1—C6	124.83 (19)	O3—C11—H11B	109.5
N2—N1—C6	112.57 (18)	H11A—C11—H11B	109.5
N1—N2—N3	105.25 (17)	O3—C11—H11C	109.5
N2—N3—C1	111.34 (18)	H11A—C11—H11C	109.5
N2—N3—C7	122.05 (18)	H11B—C11—H11C	109.5
C1—N3—C7	126.62 (19)	N6—C12—C17	105.70 (19)
O4—N4—N5	122.44 (18)	N6—C12—C13	134.4 (2)
O4—N4—C17	125.01 (19)	C17—C12—C13	119.9 (2)
N5—N4—C17	112.55 (18)	C14—C13—C12	116.2 (2)
N4—N5—N6	105.29 (16)	C14—C13—H13A	121.9
N5—N6—C12	110.97 (18)	C12—C13—H13A	121.9
N5—N6—C18	121.38 (18)	C13—C14—C15	122.9 (2)
C12—N6—C18	127.49 (19)	C13—C14—H14A	118.6
N3—C1—C6	105.28 (19)	C15—C14—H14A	118.6
N3—C1—C2	134.4 (2)	C16—C15—C14	121.4 (2)
C6—C1—C2	120.3 (2)	C16—C15—H15A	119.3
C3—C2—C1	115.9 (2)	C14—C15—H15A	119.3
C3—C2—H2B	122.0	C15—C16—C17	115.1 (2)
C1—C2—H2B	122.0	C15—C16—H16A	122.5
C2—C3—C4	122.9 (2)	C17—C16—H16A	122.5
C2—C3—H3A	118.5	C16—C17—C12	124.5 (2)
C4—C3—H3A	118.5	C16—C17—N4	130.1 (2)
C5—C4—C3	121.9 (2)	C12—C17—N4	105.49 (19)
C5—C4—H4A	119.0	O5—C18—N6	116.1 (2)
C3—C4—H4A	119.0	O5—C18—C19	129.0 (2)
C4—C5—C6	114.7 (2)	N6—C18—C19	114.9 (2)
C4—C5—H5B	122.7	C20—C19—C18	121.6 (2)
C6—C5—H5B	122.7	C20—C19—H19A	119.2
C5—C6—C1	124.3 (2)	C18—C19—H19A	119.2
C5—C6—N1	130.1 (2)	O6—C20—C19	122.4 (2)
C1—C6—N1	105.56 (19)	O6—C20—C21	111.0 (2)
O2—C7—N3	115.7 (2)	C19—C20—C21	126.7 (2)
O2—C7—C8	129.2 (2)	C20—C21—H21A	109.5
N3—C7—C8	115.1 (2)	C20—C21—H21B	109.5
C9—C8—C7	122.7 (2)	H21A—C21—H21B	109.5
C9—C8—H8A	118.7	C20—C21—H21C	109.5
C7—C8—H8A	118.7	H21A—C21—H21C	109.5
O3—C9—C8	122.4 (2)	H21B—C21—H21C	109.5
O3—C9—C10	110.3 (2)	O6—C22—H22A	109.5
C8—C9—C10	127.3 (2)	O6—C22—H22B	109.5
C9—C10—H10A	109.5	H22A—C22—H22B	109.5
C9—C10—H10B	109.5	O6—C22—H22C	109.5
H10A—C10—H10B	109.5	H22A—C22—H22C	109.5
C9—C10—H10C	109.5	H22B—C22—H22C	109.5

O1—N1—N2—N3	−179.03 (19)	C11—O3—C9—C8	−1.1 (3)
C6—N1—N2—N3	0.4 (2)	C11—O3—C9—C10	179.8 (2)
N1—N2—N3—C1	0.1 (2)	C7—C8—C9—O3	179.0 (2)
N1—N2—N3—C7	−179.59 (19)	C7—C8—C9—C10	−2.1 (4)
O4—N4—N5—N6	178.92 (19)	N5—N6—C12—C17	0.4 (2)
C17—N4—N5—N6	0.1 (2)	C18—N6—C12—C17	175.7 (2)
N4—N5—N6—C12	−0.3 (2)	N5—N6—C12—C13	−179.2 (2)
N4—N5—N6—C18	−175.93 (19)	C18—N6—C12—C13	−3.9 (4)
N2—N3—C1—C6	−0.5 (2)	N6—C12—C13—C14	179.9 (2)
C7—N3—C1—C6	179.1 (2)	C17—C12—C13—C14	0.3 (3)
N2—N3—C1—C2	178.3 (2)	C12—C13—C14—C15	0.0 (4)
C7—N3—C1—C2	−2.0 (4)	C13—C14—C15—C16	−0.6 (4)
N3—C1—C2—C3	−178.7 (2)	C14—C15—C16—C17	0.9 (3)
C6—C1—C2—C3	0.0 (3)	C15—C16—C17—C12	−0.6 (3)
C1—C2—C3—C4	−0.4 (4)	C15—C16—C17—N4	−179.8 (2)
C2—C3—C4—C5	0.3 (4)	N6—C12—C17—C16	−179.7 (2)
C3—C4—C5—C6	0.2 (4)	C13—C12—C17—C16	0.0 (4)
C4—C5—C6—C1	−0.5 (4)	N6—C12—C17—N4	−0.3 (2)
C4—C5—C6—N1	177.9 (2)	C13—C12—C17—N4	179.4 (2)
N3—C1—C6—C5	179.5 (2)	O4—N4—C17—C16	0.7 (4)
C2—C1—C6—C5	0.4 (4)	N5—N4—C17—C16	179.5 (2)
N3—C1—C6—N1	0.7 (2)	O4—N4—C17—C12	−178.6 (2)
C2—C1—C6—N1	−178.3 (2)	N5—N4—C17—C12	0.2 (3)
O1—N1—C6—C5	0.0 (4)	N5—N6—C18—O5	177.7 (2)
N2—N1—C6—C5	−179.4 (2)	C12—N6—C18—O5	2.8 (3)
O1—N1—C6—C1	178.7 (2)	N5—N6—C18—C19	−3.0 (3)
N2—N1—C6—C1	−0.7 (3)	C12—N6—C18—C19	−177.9 (2)
N2—N3—C7—O2	−175.4 (2)	O5—C18—C19—C20	5.0 (4)
C1—N3—C7—O2	5.0 (3)	N6—C18—C19—C20	−174.2 (2)
N2—N3—C7—C8	4.4 (3)	C22—O6—C20—C19	3.0 (3)
C1—N3—C7—C8	−175.3 (2)	C22—O6—C20—C21	−177.4 (2)
O2—C7—C8—C9	−0.7 (4)	C18—C19—C20—O6	179.3 (2)
N3—C7—C8—C9	179.6 (2)	C18—C19—C20—C21	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2	0.95	2.45	2.925 (3)	111
C13—H13A···O5	0.95	2.49	2.961 (3)	111
C14—H14A···O4ⁱ	0.95	2.57	3.398 (3)	147
C16—H16A···O4ⁱⁱ	0.95	2.45	3.379 (3)	165

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₃
M_r	233.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.011 (3), 10.014 (2), 15.699 (3)
β (°)	100.13 (3)
V (Å³)	2168.3 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Rigaku Mercury CCD/AFC diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.959, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	15367, 3771, 3564
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.141, 1.17
No. of reflections	3771
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.28

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2	0.95	2.45	2.925 (3)	110.5
C13—H13A···O5	0.95	2.49	2.961 (3)	110.7
C14—H14A···O4ⁱ	0.95	2.57	3.398 (3)	146.5
C16—H16A···O4ⁱⁱ	0.95	2.45	3.379 (3)	164.6

Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y−1, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Barlos, K., Papaioannou, D., Voliotis, S., Prewo, R. & Bieri, J. H. (1985). J. Org. Chem. pp. 696–697. CSD CrossRef Web of Science Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, J., Fox, R., Wong, M., Kissick, T. P., Moniot, J. L., Gougoutas, J. Z., Malley, M. F. & Kocy, O. (1988). J. Org. Chem. pp. 208–210. Google Scholar
Zhang, Y., Sun, X. W., Hui, X. E. & Zhang, Q. (2002). Chin. J. Chem. 20, 168–172. CrossRef CAS Google Scholar

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Volume 66| Part 1| January 2010| Page o13

doi:10.1107/S1600536809050442

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