3-[(R)-1-Hy-droxy-butan-2-yl]-1,2,3-benzo-triazin-4(3H)-one.

The crystal structure of the title compound, C(11)H(13)N(3)O(2), is stabilized by O-H⋯O hydrogen bonds, which link the mol-ecules into chains along [100].

Related literature

For biological and synthetic applications of benzo-1,2,3-triazinones, see: Caliendo et al. (1999 ▶); Zheng et al. (2005 ▶); Vaisburg et al. (2004 ▶); Chollet et al. (2002 ▶); Le Diguarher et al. (2003 ▶); Clark et al. (1995 ▶); Carpino et al. (2004 ▶); Janout et al. (2003 ▶); Gierasch et al. (2000 ▶). For structures of benzo-1,2,3-triazinones, see: Hjortås et al. (1973 ▶); Hunt et al. (1983 ▶); Reingruber et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the synthesis, see: Gómez et al. (2005 ▶).

Experimental

Crystal data

C11H13N3O2

M = 219.24

Orthorhombic,

a = 8.9668 (13) Å

b = 10.1506 (15) Å

c = 12.0238 (17) Å

V = 1094.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.32 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

9057 measured reflections

2000 independent reflections

1700 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.076

S = 0.93

2000 reflections

149 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043802/zj2097sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043802/zj2097Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043802/zj2097Isup3.cml

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

C11H13N3O2	F(000) = 464
Mr = 219.24	Dx = 1.331 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4276 reflections
a = 8.9668 (13) Å	θ = 2.6–25.2°
b = 10.1506 (15) Å	µ = 0.09 mm−1
c = 12.0238 (17) Å	T = 298 K
V = 1094.4 (3) Å3	Prism, colourless
Z = 4	0.32 × 0.10 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	1700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 25.4°, θmin = 2.6°
Detector resolution: 0.83 pixels mm-1	h = −10→10
ω scans	k = −12→12
9057 measured reflections	l = −14→14
2000 independent reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
2000 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.15 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
O1	0.56004 (14)	0.68985 (11)	1.02583 (10)	0.0584 (4)
N1	0.87770 (16)	0.64809 (13)	0.79106 (11)	0.0438 (4)
O2	0.82337 (18)	0.99854 (13)	0.99816 (15)	0.0797 (5)
H2	0.885 (2)	0.9362 (16)	0.992 (2)	0.096*
N2	0.80536 (16)	0.75426 (13)	0.80106 (11)	0.0430 (4)
N3	0.70312 (14)	0.76906 (12)	0.88520 (11)	0.0372 (3)
C4	0.66320 (18)	0.67321 (15)	0.96026 (14)	0.0386 (4)
C4A	0.75154 (18)	0.55429 (16)	0.95179 (13)	0.0362 (4)
C5	0.7338 (2)	0.44941 (16)	1.02537 (14)	0.0469 (4)
H5	0.6642	0.4546	1.0826	0.056*
C6	0.8194 (2)	0.33848 (17)	1.01301 (16)	0.0545 (5)
H6	0.8081	0.2686	1.0623	0.065*
C7	0.9226 (2)	0.32979 (18)	0.92741 (17)	0.0568 (5)
H7	0.9790	0.2535	0.9191	0.068*
C8	0.94229 (19)	0.43244 (17)	0.85511 (16)	0.0517 (5)
H8	1.0127	0.4266	0.7985	0.062*
C8A	0.85625 (17)	0.54564 (15)	0.86684 (13)	0.0382 (4)
C9	0.62783 (18)	0.89954 (14)	0.88408 (15)	0.0420 (4)
H9	0.5594	0.9021	0.9476	0.050*
C10	0.7406 (2)	1.00892 (17)	0.89991 (17)	0.0553 (5)
H10A	0.8088	1.0088	0.8372	0.066*
H10B	0.6886	1.0927	0.8998	0.066*
C11	0.5352 (2)	0.91729 (17)	0.77929 (16)	0.0559 (5)
H11A	0.4838	1.0012	0.7833	0.067*
H11B	0.6015	0.9202	0.7156	0.067*
C12	0.4222 (2)	0.80997 (19)	0.76146 (19)	0.0765 (7)
H12A	0.3540	0.8081	0.8230	0.092*
H12B	0.4722	0.7266	0.7560	0.092*
H12C	0.3681	0.8266	0.6940	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0643 (8)	0.0449 (7)	0.0660 (9)	0.0042 (7)	0.0294 (8)	0.0035 (6)
N1	0.0471 (8)	0.0409 (8)	0.0434 (8)	0.0020 (7)	0.0101 (7)	−0.0012 (7)
O2	0.0754 (11)	0.0612 (10)	0.1026 (12)	0.0097 (8)	−0.0365 (10)	−0.0201 (9)
N2	0.0473 (8)	0.0401 (8)	0.0415 (8)	0.0014 (7)	0.0075 (7)	0.0013 (7)
N3	0.0410 (8)	0.0319 (7)	0.0387 (8)	0.0029 (6)	0.0047 (7)	0.0002 (6)
C4	0.0396 (9)	0.0364 (9)	0.0398 (9)	−0.0021 (8)	0.0043 (8)	−0.0018 (8)
C4A	0.0380 (9)	0.0339 (8)	0.0366 (9)	−0.0030 (7)	−0.0024 (8)	−0.0013 (7)
C5	0.0532 (11)	0.0426 (10)	0.0448 (10)	−0.0046 (9)	−0.0004 (9)	0.0019 (8)
C6	0.0638 (12)	0.0392 (10)	0.0604 (12)	−0.0009 (9)	−0.0109 (10)	0.0083 (9)
C7	0.0538 (12)	0.0365 (10)	0.0800 (14)	0.0100 (9)	−0.0071 (11)	−0.0013 (10)
C8	0.0435 (10)	0.0465 (11)	0.0651 (12)	0.0061 (9)	0.0060 (9)	−0.0089 (10)
C8A	0.0379 (9)	0.0352 (9)	0.0416 (10)	−0.0030 (7)	−0.0017 (8)	−0.0044 (8)
C9	0.0457 (9)	0.0337 (9)	0.0467 (10)	0.0058 (7)	0.0009 (9)	−0.0019 (8)
C10	0.0587 (11)	0.0362 (10)	0.0711 (12)	0.0034 (8)	−0.0022 (12)	−0.0055 (9)
C11	0.0648 (12)	0.0429 (10)	0.0600 (12)	0.0132 (9)	−0.0118 (10)	−0.0007 (9)
C12	0.0765 (14)	0.0602 (13)	0.0927 (17)	0.0111 (12)	−0.0357 (14)	−0.0133 (12)

O1—C4	1.2271 (18)	C7—C8	1.368 (2)
N1—N2	1.2636 (17)	C7—H7	0.9300
N1—C8A	1.396 (2)	C8—C8A	1.391 (2)
O2—C10	1.399 (2)	C8—H8	0.9300
O2—H2	0.846 (9)	C9—C10	1.514 (2)
N2—N3	1.3735 (18)	C9—C11	1.520 (2)
N3—C4	1.3745 (19)	C9—H9	0.9800
N3—C9	1.4866 (19)	C10—H10A	0.9700
C4—C4A	1.447 (2)	C10—H10B	0.9700
C4A—C8A	1.390 (2)	C11—C12	1.503 (2)
C4A—C5	1.393 (2)	C11—H11A	0.9700
C5—C6	1.371 (2)	C11—H11B	0.9700
C5—H5	0.9300	C12—H12A	0.9600
C6—C7	1.387 (3)	C12—H12B	0.9600
C6—H6	0.9300	C12—H12C	0.9600
N2—N1—C8A	120.17 (13)	C8—C8A—N1	118.22 (15)
C10—O2—H2	109.5 (17)	N3—C9—C10	110.42 (13)
N1—N2—N3	120.40 (12)	N3—C9—C11	111.17 (14)
N2—N3—C4	125.45 (12)	C10—C9—C11	112.49 (14)
N2—N3—C9	113.20 (12)	N3—C9—H9	107.5
C4—N3—C9	121.22 (13)	C10—C9—H9	107.5
O1—C4—N3	121.38 (14)	C11—C9—H9	107.5
O1—C4—C4A	124.93 (15)	O2—C10—C9	113.91 (15)
N3—C4—C4A	113.68 (14)	O2—C10—H10A	108.8
C8A—C4A—C5	119.70 (15)	C9—C10—H10A	108.8
C8A—C4A—C4	118.29 (14)	O2—C10—H10B	108.8
C5—C4A—C4	122.01 (15)	C9—C10—H10B	108.8
C6—C5—C4A	119.66 (17)	H10A—C10—H10B	107.7
C6—C5—H5	120.2	C12—C11—C9	113.63 (15)
C4A—C5—H5	120.2	C12—C11—H11A	108.8
C5—C6—C7	120.42 (17)	C9—C11—H11A	108.8
C5—C6—H6	119.8	C12—C11—H11B	108.8
C7—C6—H6	119.8	C9—C11—H11B	108.8
C8—C7—C6	120.59 (17)	H11A—C11—H11B	107.7
C8—C7—H7	119.7	C11—C12—H12A	109.5
C6—C7—H7	119.7	C11—C12—H12B	109.5
C7—C8—C8A	119.55 (17)	H12A—C12—H12B	109.5
C7—C8—H8	120.2	C11—C12—H12C	109.5
C8A—C8—H8	120.2	H12A—C12—H12C	109.5
C4A—C8A—C8	120.07 (15)	H12B—C12—H12C	109.5
C4A—C8A—N1	121.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.85 (1)	2.03 (1)	2.8712 (19)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.85 (1)	2.03 (1)	2.8712 (19)	171 (2)

Symmetry code: (i) .