2-Hy-droxy-7-meth-oxy-9H-carbazole-3-carbaldehyde.

The title compound, C(14)H(11)NO(3), was isolated from the roots of Clausena wallichii. The carbazole ring system is approx-imately planar (r.m.s. deviation = 0.039 Å) and the dihedral angle between the two benzene rings is 4.63 (7)°. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked into a zigzag network extending parallel to the ac plane by O-H⋯N and N-H⋯O hydrogen bonds.

Related literature

For compounds isolated from plants of genera Rutaceae and their pharmacological activity, see: Ito et al. (1997 ▶); Kongkathip & Kongkathip (2009 ▶); Laphookhieo et al. (2009 ▶); Li et al. (1991 ▶); Maneerat & Laphookhieo (2010 ▶); Maneerat et al. (2010 ▶); Sripisut & Laphookhieo (2010 ▶); Tangyuenyongwatthana et al. (1992 ▶); Yenjai et al. 2000 ▶). For a related structure, see: Fun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C14H11NO3

M = 241.24

Orthorhombic,

a = 12.4352 (4) Å

b = 17.6564 (5) Å

c = 5.0839 (1) Å

V = 1116.23 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.84 mm−1

T = 100 K

0.23 × 0.19 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.831, T max = 0.918

25207 measured reflections

2026 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.097

S = 1.31

2026 reflections

170 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.63 e Å−3

Absolute structure: Flack (1983 ▶), 851 Friedel pairs

Flack parameter: 0.17 (19)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033805/ci5167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033805/ci5167Isup2.hkl

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

C14H11NO3	Dx = 1.435 Mg m−3
Mr = 241.24	Melting point = 496.7–498.8 K
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 2026 reflections
a = 12.4352 (4) Å	θ = 4.4–69.9°
b = 17.6564 (5) Å	µ = 0.84 mm−1
c = 5.0839 (1) Å	T = 100 K
V = 1116.23 (5) Å3	Plate, yellow
Z = 4	0.23 × 0.19 × 0.10 mm
F(000) = 504

Bruker APEXII DUO CCD area-detector diffractometer	2026 independent reflections
Radiation source: sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 69.9°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.831, Tmax = 0.918	k = −21→21
25207 measured reflections	l = −5→6

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0656P)2 + 0.054P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max = 0.001
S = 1.31	Δρmax = 0.64 e Å−3
2026 reflections	Δρmin = −0.63 e Å−3
170 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.053 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 851 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.17 (19)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.59667 (8)	0.17861 (6)	0.4400 (2)	0.0264 (3)
H1O1	0.6537	0.1796	0.5149	0.056 (7)*
O2	0.72058 (8)	0.20104 (6)	0.8557 (3)	0.0294 (3)
O3	0.12071 (9)	0.59553 (6)	0.5822 (3)	0.0325 (3)
N1	0.32559 (9)	0.37021 (7)	0.3111 (3)	0.0203 (3)
H1N1	0.2898 (14)	0.3514 (10)	0.185 (5)	0.029 (5)*
C1	0.46098 (10)	0.26763 (8)	0.3568 (3)	0.0213 (3)
H1A	0.4366	0.2391	0.2150	0.026*
C2	0.54764 (10)	0.24453 (8)	0.5070 (3)	0.0212 (3)
C3	0.58509 (11)	0.28796 (8)	0.7249 (3)	0.0220 (3)
C4	0.53291 (10)	0.35607 (8)	0.7921 (3)	0.0208 (3)
H4A	0.5569	0.3847	0.9339	0.025*
C5	0.36091 (11)	0.50464 (7)	0.8333 (3)	0.0226 (3)
H5A	0.4092	0.5117	0.9708	0.027*
C6	0.27613 (11)	0.55440 (8)	0.7967 (3)	0.0241 (3)
H6A	0.2680	0.5955	0.9094	0.029*
C7	0.20217 (11)	0.54348 (8)	0.5906 (3)	0.0238 (3)
C8	0.21259 (10)	0.48413 (7)	0.4134 (3)	0.0222 (4)
H8A	0.1644	0.4774	0.2756	0.027*
C9	0.29943 (10)	0.43496 (7)	0.4528 (3)	0.0195 (3)
C10	0.41167 (10)	0.33567 (7)	0.4277 (3)	0.0196 (3)
C11	0.44591 (10)	0.37986 (8)	0.6456 (3)	0.0194 (3)
C12	0.37263 (11)	0.44372 (8)	0.6603 (3)	0.0203 (3)
C13	0.67188 (10)	0.26163 (8)	0.8877 (3)	0.0244 (3)
H13A	0.6930	0.2923	1.0273	0.029*
C14	0.03861 (12)	0.58496 (9)	0.3899 (4)	0.0354 (4)
H14A	−0.0179	0.6211	0.4184	0.053*
H14B	0.0101	0.5346	0.4043	0.053*
H14C	0.0684	0.5921	0.2174	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0261 (5)	0.0281 (5)	0.0251 (6)	0.0080 (4)	−0.0009 (4)	−0.0024 (5)
O2	0.0282 (5)	0.0358 (6)	0.0241 (7)	0.0098 (4)	−0.0016 (4)	0.0011 (5)
O3	0.0345 (6)	0.0291 (6)	0.0340 (7)	0.0104 (4)	−0.0052 (5)	−0.0053 (5)
N1	0.0207 (6)	0.0215 (6)	0.0187 (6)	0.0000 (4)	−0.0025 (5)	−0.0007 (5)
C1	0.0224 (6)	0.0225 (7)	0.0188 (8)	−0.0013 (5)	0.0010 (6)	−0.0003 (5)
C2	0.0202 (6)	0.0226 (6)	0.0209 (8)	0.0007 (5)	0.0047 (5)	0.0017 (6)
C3	0.0206 (7)	0.0242 (7)	0.0212 (8)	−0.0011 (5)	0.0019 (6)	0.0032 (6)
C4	0.0207 (6)	0.0234 (7)	0.0183 (8)	−0.0035 (5)	0.0000 (5)	0.0005 (6)
C5	0.0257 (7)	0.0221 (7)	0.0199 (7)	−0.0044 (5)	−0.0007 (6)	0.0000 (6)
C6	0.0303 (7)	0.0204 (6)	0.0217 (8)	−0.0017 (5)	0.0022 (6)	−0.0028 (6)
C7	0.0258 (7)	0.0210 (7)	0.0246 (8)	0.0016 (5)	0.0025 (6)	0.0029 (6)
C8	0.0226 (7)	0.0224 (7)	0.0216 (9)	−0.0004 (5)	−0.0014 (5)	0.0023 (6)
C9	0.0201 (6)	0.0195 (6)	0.0191 (8)	−0.0028 (5)	0.0020 (5)	0.0005 (6)
C10	0.0179 (6)	0.0217 (7)	0.0193 (8)	−0.0026 (4)	0.0014 (5)	0.0020 (6)
C11	0.0211 (6)	0.0191 (6)	0.0180 (8)	−0.0036 (5)	0.0023 (5)	0.0016 (5)
C12	0.0214 (7)	0.0188 (6)	0.0206 (8)	−0.0030 (5)	0.0015 (5)	0.0031 (6)
C13	0.0238 (6)	0.0297 (7)	0.0198 (9)	−0.0003 (5)	−0.0001 (6)	0.0025 (6)
C14	0.0353 (8)	0.0360 (9)	0.0348 (11)	0.0131 (6)	−0.0077 (7)	−0.0022 (8)

O1—C2	1.3574 (17)	C5—C6	1.3850 (19)
O1—H1O1	0.81	C5—C12	1.397 (2)
O2—C13	1.2401 (17)	C5—H5A	0.93
O3—C7	1.3685 (16)	C6—C7	1.407 (2)
O3—C14	1.426 (2)	C6—H6A	0.93
N1—C10	1.3671 (18)	C7—C8	1.388 (2)
N1—C9	1.3899 (18)	C8—C9	1.4000 (17)
N1—H1N1	0.85 (2)	C8—H8A	0.93
C1—C2	1.382 (2)	C9—C12	1.402 (2)
C1—C10	1.3960 (18)	C10—C11	1.420 (2)
C1—H1A	0.93	C11—C12	1.4517 (18)
C2—C3	1.425 (2)	C13—H13A	0.93
C3—C4	1.4086 (19)	C14—H14A	0.96
C3—C13	1.438 (2)	C14—H14B	0.96
C4—C11	1.379 (2)	C14—H14C	0.96
C4—H4A	0.93
C2—O1—H1O1	104.9	C8—C7—C6	121.71 (13)
C7—O3—C14	117.62 (13)	C7—C8—C9	116.58 (13)
C10—N1—C9	109.00 (13)	C7—C8—H8A	121.7
C10—N1—H1N1	124.3 (12)	C9—C8—H8A	121.7
C9—N1—H1N1	126.2 (12)	N1—C9—C8	128.06 (14)
C2—C1—C10	116.99 (14)	N1—C9—C12	109.20 (12)
C2—C1—H1A	121.5	C8—C9—C12	122.69 (13)
C10—C1—H1A	121.5	N1—C10—C1	128.02 (14)
O1—C2—C1	117.68 (14)	N1—C10—C11	109.13 (12)
O1—C2—C3	120.64 (13)	C1—C10—C11	122.84 (13)
C1—C2—C3	121.67 (13)	C4—C11—C10	119.28 (13)
C4—C3—C2	119.83 (13)	C4—C11—C12	134.53 (14)
C4—C3—C13	118.83 (14)	C10—C11—C12	106.18 (12)
C2—C3—C13	121.25 (13)	C5—C12—C9	119.41 (12)
C11—C4—C3	119.36 (14)	C5—C12—C11	134.10 (14)
C11—C4—H4A	120.3	C9—C12—C11	106.45 (12)
C3—C4—H4A	120.3	O2—C13—C3	124.75 (14)
C6—C5—C12	118.88 (14)	O2—C13—H13A	117.6
C6—C5—H5A	120.6	C3—C13—H13A	117.6
C12—C5—H5A	120.6	O3—C14—H14A	109.5
C5—C6—C7	120.71 (14)	O3—C14—H14B	109.5
C5—C6—H6A	119.6	H14A—C14—H14B	109.5
C7—C6—H6A	119.6	O3—C14—H14C	109.5
O3—C7—C8	123.77 (14)	H14A—C14—H14C	109.5
O3—C7—C6	114.52 (14)	H14B—C14—H14C	109.5
C10—C1—C2—O1	−179.79 (13)	C2—C1—C10—N1	179.92 (13)
C10—C1—C2—C3	0.13 (19)	C2—C1—C10—C11	−1.0 (2)
O1—C2—C3—C4	−179.74 (12)	C3—C4—C11—C10	−0.9 (2)
C1—C2—C3—C4	0.3 (2)	C3—C4—C11—C12	177.97 (14)
O1—C2—C3—C13	−3.2 (2)	N1—C10—C11—C4	−179.38 (12)
C1—C2—C3—C13	176.88 (12)	C1—C10—C11—C4	1.4 (2)
C2—C3—C4—C11	0.0 (2)	N1—C10—C11—C12	1.49 (15)
C13—C3—C4—C11	−176.59 (13)	C1—C10—C11—C12	−177.74 (12)
C12—C5—C6—C7	0.7 (2)	C6—C5—C12—C9	0.8 (2)
C14—O3—C7—C8	4.0 (2)	C6—C5—C12—C11	−176.30 (14)
C14—O3—C7—C6	−175.73 (14)	N1—C9—C12—C5	−178.86 (12)
C5—C6—C7—O3	178.13 (13)	C8—C9—C12—C5	−1.4 (2)
C5—C6—C7—C8	−1.7 (2)	N1—C9—C12—C11	−1.06 (15)
O3—C7—C8—C9	−178.74 (13)	C8—C9—C12—C11	176.40 (12)
C6—C7—C8—C9	1.0 (2)	C4—C11—C12—C5	−1.9 (3)
C10—N1—C9—C8	−175.26 (13)	C10—C11—C12—C5	177.08 (15)
C10—N1—C9—C12	2.04 (15)	C4—C11—C12—C9	−179.18 (15)
C7—C8—C9—N1	177.45 (14)	C10—C11—C12—C9	−0.25 (15)
C7—C8—C9—C12	0.49 (19)	C4—C3—C13—O2	176.58 (13)
C9—N1—C10—C1	176.99 (13)	C2—C3—C13—O2	0.0 (2)
C9—N1—C10—C11	−2.19 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.81	1.96	2.6453 (17)	143
O1—H1O1···N1i	0.81	2.53	3.0457 (15)	123
N1—H1N1···O2ii	0.85 (2)	2.10 (2)	2.941 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.81	1.96	2.6453 (17)	143
O1—H1O1⋯N1i	0.81	2.53	3.0457 (15)	123
N1—H1N1⋯O2ii	0.85 (2)	2.10 (2)	2.941 (2)	172 (2)

Symmetry codes: (i) ; (ii) .