Glycozolidal.

THE TITLE COMPOUND KNOWN AS GLYCOZOLIDAL (SYSTEMATIC NAME: 2,7-dimeth-oxy-9H-carbazole-3-carbaldehyde), C(15)H(13)NO(3), is a naturally occurring carbazole, which was isolated from the roots of Clausena lansium. The carbazole ring system is essentially planar, with an r.m.s. deviation of 0.0093 (1) Å. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into a chain along the c axis. C-H⋯O, C-H⋯π and π-π inter-actions, with centroid-centroid distances of 3.5924 (6), 3.6576 (6) and 3.8613 (6) Å, are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to carbazole alkaloids and their activities, see: 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 ▶); Thongthoom et al. (2010 ▶); Yenjai et al. (2000 ▶). For related structures, see: Fun et al. (2007 ▶, 2009 ▶, 2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H13NO3

M = 255.26

Monoclinic,

a = 20.5756 (4) Å

b = 8.1298 (1) Å

c = 14.0411 (3) Å

β = 98.871 (1)°

V = 2320.64 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.53 × 0.42 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.947, T max = 0.984

13003 measured reflections

3381 independent reflections

3032 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.04

3381 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811024160/is2736sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024160/is2736Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024160/is2736Isup3.cml

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

C15H13NO3	F(000) = 1072
Mr = 255.26	Dx = 1.461 Mg m−3
Monoclinic, C2/c	Melting point = 469.6–470.7 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.5756 (4) Å	Cell parameters from 3381 reflections
b = 8.1298 (1) Å	θ = 2.0–30.0°
c = 14.0411 (3) Å	µ = 0.10 mm−1
β = 98.871 (1)°	T = 100 K
V = 2320.64 (7) Å3	Block, yellow
Z = 8	0.53 × 0.42 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	3381 independent reflections
Radiation source: sealed tube	3032 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→28
Tmin = 0.947, Tmax = 0.984	k = −11→9
13003 measured reflections	l = −19→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0682P)2 + 1.6186P] where P = (Fo2 + 2Fc2)/3
3381 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.06869 (4)	0.45177 (10)	0.60778 (5)	0.01915 (17)
O2	0.01915 (4)	0.13634 (10)	0.39162 (6)	0.02408 (18)
O3	0.34527 (3)	0.26588 (9)	0.16940 (5)	0.01588 (16)
N1	0.27840 (4)	0.55708 (10)	0.49606 (6)	0.01503 (17)
H1N1	0.2977 (8)	0.626 (2)	0.5410 (12)	0.031 (4)*
C1	0.17456 (5)	0.51795 (12)	0.56255 (7)	0.01507 (18)
H1A	0.1855	0.5922	0.6148	0.018*
C2	0.11513 (5)	0.43366 (12)	0.54868 (7)	0.01486 (19)
C3	0.09900 (5)	0.32215 (12)	0.47030 (7)	0.01479 (18)
C4	0.14322 (5)	0.29659 (12)	0.40535 (7)	0.01420 (18)
H4A	0.1325	0.2221	0.3532	0.017*
C5	0.27380 (4)	0.30870 (12)	0.28279 (7)	0.01392 (18)
H5A	0.2440	0.2330	0.2479	0.017*
C6	0.33378 (5)	0.34504 (12)	0.25284 (7)	0.01366 (18)
C7	0.37905 (5)	0.45348 (12)	0.30457 (7)	0.01510 (18)
H7A	0.4196	0.4759	0.2826	0.018*
C8	0.36473 (5)	0.52877 (12)	0.38837 (7)	0.01506 (19)
H8A	0.3955	0.6003	0.4248	0.018*
C9	0.30431 (5)	0.49645 (12)	0.41708 (7)	0.01365 (18)
C10	0.25861 (4)	0.38624 (11)	0.36532 (6)	0.01310 (18)
C11	0.20281 (4)	0.38018 (11)	0.41712 (6)	0.01329 (18)
C12	0.21752 (4)	0.48914 (11)	0.49667 (7)	0.01357 (18)
C13	0.08690 (5)	0.55135 (13)	0.69203 (7)	0.0199 (2)
H13A	0.0510	0.5519	0.7305	0.030*
H13B	0.0955	0.6641	0.6726	0.030*
H13C	0.1266	0.5061	0.7306	0.030*
C14	0.03699 (5)	0.23074 (13)	0.45831 (8)	0.0192 (2)
H14A	0.0089	0.2457	0.5053	0.023*
C15	0.41126 (5)	0.27000 (14)	0.14839 (8)	0.0200 (2)
H15A	0.4153	0.1932	0.0958	0.030*
H15B	0.4419	0.2380	0.2059	0.030*
H15C	0.4217	0.3816	0.1291	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0164 (3)	0.0238 (4)	0.0186 (4)	−0.0010 (3)	0.0070 (3)	−0.0029 (3)
O2	0.0178 (4)	0.0251 (4)	0.0294 (4)	−0.0050 (3)	0.0038 (3)	−0.0061 (3)
O3	0.0146 (3)	0.0201 (3)	0.0135 (3)	0.0005 (2)	0.0042 (2)	−0.0016 (2)
N1	0.0141 (4)	0.0167 (4)	0.0145 (4)	−0.0030 (3)	0.0028 (3)	−0.0026 (3)
C1	0.0157 (4)	0.0159 (4)	0.0137 (4)	−0.0003 (3)	0.0025 (3)	−0.0008 (3)
C2	0.0142 (4)	0.0162 (4)	0.0147 (4)	0.0011 (3)	0.0039 (3)	0.0015 (3)
C3	0.0135 (4)	0.0156 (4)	0.0154 (4)	−0.0007 (3)	0.0025 (3)	0.0012 (3)
C4	0.0144 (4)	0.0145 (4)	0.0136 (4)	−0.0010 (3)	0.0017 (3)	0.0007 (3)
C5	0.0139 (4)	0.0143 (4)	0.0134 (4)	−0.0007 (3)	0.0018 (3)	0.0004 (3)
C6	0.0149 (4)	0.0145 (4)	0.0118 (4)	0.0013 (3)	0.0029 (3)	0.0010 (3)
C7	0.0133 (4)	0.0164 (4)	0.0157 (4)	−0.0014 (3)	0.0029 (3)	0.0016 (3)
C8	0.0143 (4)	0.0156 (4)	0.0152 (4)	−0.0026 (3)	0.0021 (3)	0.0004 (3)
C9	0.0138 (4)	0.0137 (4)	0.0133 (4)	−0.0004 (3)	0.0018 (3)	0.0006 (3)
C10	0.0129 (4)	0.0138 (4)	0.0127 (4)	−0.0006 (3)	0.0021 (3)	0.0014 (3)
C11	0.0134 (4)	0.0143 (4)	0.0123 (4)	−0.0004 (3)	0.0024 (3)	0.0008 (3)
C12	0.0132 (4)	0.0140 (4)	0.0133 (4)	−0.0003 (3)	0.0015 (3)	0.0012 (3)
C13	0.0226 (5)	0.0206 (5)	0.0178 (5)	0.0012 (4)	0.0074 (4)	−0.0015 (4)
C14	0.0143 (4)	0.0206 (5)	0.0232 (5)	−0.0019 (3)	0.0047 (3)	−0.0002 (4)
C15	0.0166 (4)	0.0243 (5)	0.0204 (5)	−0.0012 (4)	0.0073 (4)	−0.0016 (4)

O1—C2	1.3667 (11)	C5—C10	1.3962 (13)
O1—C13	1.4347 (13)	C5—H5A	0.9500
O2—C14	1.2225 (13)	C6—C7	1.4013 (13)
O3—C6	1.3887 (11)	C7—C8	1.3975 (13)
O3—C15	1.4337 (11)	C7—H7A	0.9500
N1—C12	1.3702 (11)	C8—C9	1.3896 (13)
N1—C9	1.3927 (12)	C8—H8A	0.9500
N1—H1N1	0.890 (17)	C9—C10	1.4158 (13)
C1—C2	1.3890 (13)	C10—C11	1.4516 (12)
C1—C12	1.3944 (13)	C11—C12	1.4212 (13)
C1—H1A	0.9500	C13—H13A	0.9800
C2—C3	1.4250 (13)	C13—H13B	0.9800
C3—C4	1.3995 (13)	C13—H13C	0.9800
C3—C14	1.4637 (13)	C14—H14A	0.9500
C4—C11	1.3892 (13)	C15—H15A	0.9800
C4—H4A	0.9500	C15—H15B	0.9800
C5—C6	1.3954 (12)	C15—H15C	0.9800
C2—O1—C13	116.31 (8)	C7—C8—H8A	120.8
C6—O3—C15	116.91 (8)	C8—C9—N1	129.31 (9)
C12—N1—C9	108.96 (8)	C8—C9—C10	121.59 (9)
C12—N1—H1N1	123.8 (11)	N1—C9—C10	109.10 (8)
C9—N1—H1N1	127.2 (11)	C5—C10—C9	119.72 (8)
C2—C1—C12	117.29 (9)	C5—C10—C11	134.11 (8)
C2—C1—H1A	121.4	C9—C10—C11	106.16 (8)
C12—C1—H1A	121.4	C4—C11—C12	118.40 (8)
O1—C2—C1	122.99 (9)	C4—C11—C10	135.13 (9)
O1—C2—C3	115.86 (8)	C12—C11—C10	106.47 (8)
C1—C2—C3	121.15 (9)	N1—C12—C1	127.59 (9)
C4—C3—C2	120.03 (9)	N1—C12—C11	109.30 (8)
C4—C3—C14	119.50 (9)	C1—C12—C11	123.10 (9)
C2—C3—C14	120.45 (9)	O1—C13—H13A	109.5
C11—C4—C3	120.02 (9)	O1—C13—H13B	109.5
C11—C4—H4A	120.0	H13A—C13—H13B	109.5
C3—C4—H4A	120.0	O1—C13—H13C	109.5
C6—C5—C10	118.43 (8)	H13A—C13—H13C	109.5
C6—C5—H5A	120.8	H13B—C13—H13C	109.5
C10—C5—H5A	120.8	O2—C14—C3	124.07 (10)
O3—C6—C5	115.45 (8)	O2—C14—H14A	118.0
O3—C6—C7	122.88 (8)	C3—C14—H14A	118.0
C5—C6—C7	121.67 (9)	O3—C15—H15A	109.5
C8—C7—C6	120.15 (8)	O3—C15—H15B	109.5
C8—C7—H7A	119.9	H15A—C15—H15B	109.5
C6—C7—H7A	119.9	O3—C15—H15C	109.5
C9—C8—C7	118.40 (9)	H15A—C15—H15C	109.5
C9—C8—H8A	120.8	H15B—C15—H15C	109.5
C13—O1—C2—C1	−6.03 (14)	C6—C5—C10—C11	179.98 (10)
C13—O1—C2—C3	174.23 (8)	C8—C9—C10—C5	−0.65 (14)
C12—C1—C2—O1	−179.61 (9)	N1—C9—C10—C5	−179.76 (8)
C12—C1—C2—C3	0.12 (14)	C8—C9—C10—C11	178.56 (9)
O1—C2—C3—C4	179.41 (8)	N1—C9—C10—C11	−0.55 (10)
C1—C2—C3—C4	−0.33 (14)	C3—C4—C11—C12	0.77 (14)
O1—C2—C3—C14	−2.02 (14)	C3—C4—C11—C10	−179.17 (10)
C1—C2—C3—C14	178.23 (9)	C5—C10—C11—C4	−0.18 (19)
C2—C3—C4—C11	−0.13 (14)	C9—C10—C11—C4	−179.22 (10)
C14—C3—C4—C11	−178.71 (9)	C5—C10—C11—C12	179.87 (10)
C15—O3—C6—C5	−166.26 (8)	C9—C10—C11—C12	0.83 (10)
C15—O3—C6—C7	13.32 (13)	C9—N1—C12—C1	−179.26 (9)
C10—C5—C6—O3	−178.94 (8)	C9—N1—C12—C11	0.49 (11)
C10—C5—C6—C7	1.47 (14)	C2—C1—C12—N1	−179.72 (9)
O3—C6—C7—C8	−179.69 (8)	C2—C1—C12—C11	0.56 (14)
C5—C6—C7—C8	−0.13 (14)	C4—C11—C12—N1	179.22 (8)
C6—C7—C8—C9	−1.58 (14)	C10—C11—C12—N1	−0.82 (10)
C7—C8—C9—N1	−179.11 (9)	C4—C11—C12—C1	−1.01 (14)
C7—C8—C9—C10	1.98 (14)	C10—C11—C12—C1	178.95 (9)
C12—N1—C9—C8	−178.97 (10)	C4—C3—C14—O2	−3.35 (16)
C12—N1—C9—C10	0.05 (11)	C2—C3—C14—O2	178.08 (10)
C6—C5—C10—C9	−1.08 (13)

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.890 (17)	2.106 (17)	2.9758 (11)	165.2 (15)
C15—H15C···O2ii	0.98	2.44	3.3888 (14)	162
C15—H15A···Cg2iii	0.98	2.91	3.6613 (12)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4/C11/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.890 (17)	2.106 (17)	2.9758 (11)	165.2 (15)
C15—H15C⋯O2ii	0.98	2.44	3.3888 (14)	162
C15—H15A⋯Cg2iii	0.98	2.91	3.6613 (12)	134

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