Methyl 5,6-dimeth-oxy-1H-indole-2-carboxyl-ate.

The title compound, C(12)H(13)NO(4), was prepared as a precursor to an indole derivative with possible anti-mitotic properties. The mol-ecule is very nearly planar; the maximum deviation of any non-H atom from the mean plane of the indole ring is 0.120 (3) Å for each of two meth-oxy C atoms. The pairs of mol-ecules related by the inversion centre at (0,0,) are connected by two symmetry-equivalent N-H⋯O hydrogen bonds, while the pairs of mol-ecules related by the inversion centre at (0,0,0) exhibit a π-stacking inter-action of the indole rings, with an inter-planar separation of 3.39 (3) Å.

Related literature

For related structures see: Shoja (1988a ▶,b ▶). For pharmaceutical applications see: Fuwa & Sasaki (2009 ▶); Li & Martins (2003 ▶). For a study of π–π packing inter­actions see: Janiak (2000 ▶).

Experimental

Crystal data

C12H13NO4

M = 235.23

Orthorhombic,

a = 17.0768 (19) Å

b = 7.7232 (11) Å

c = 17.678 (2) Å

V = 2331.5 (5) Å3

Z = 8

Cu Kα radiation

μ = 0.85 mm−1

T = 295 K

0.36 × 0.22 × 0.21 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

9909 measured reflections

2098 independent reflections

1522 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 171 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.102

S = 1.02

2098 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034667/fj2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034667/fj2241Isup2.hkl

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

C12H13NO4	F(000) = 992
Mr = 235.23	Dx = 1.34 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 17.0768 (19) Å	θ = 10.0–43.0°
b = 7.7232 (11) Å	µ = 0.85 mm−1
c = 17.678 (2) Å	T = 295 K
V = 2331.5 (5) Å3	Prism, colourless
Z = 8	0.36 × 0.22 × 0.21 mm

Enraf–Nonius CAD-4 diffractometer	θmax = 67.4°, θmin = 5°
Non–profiled ω/2θ scans	h = −20→20
9909 measured reflections	k = 0→9
2098 independent reflections	l = −21→21
1522 reflections with I > 2σ(I)	3 standard reflections every 171 reflections
Rint = 0.030	intensity decay: 1%

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.2248P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.035	(Δ/σ)max < 0.001
wR(F2) = 0.102	Δρmax = 0.14 e Å−3
S = 1.02	Δρmin = −0.12 e Å−3
2098 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
162 parameters	Extinction coefficient: 0.0047 (4)
0 restraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
N	0.05760 (8)	0.76815 (19)	0.51504 (7)	0.0509 (3)
O1	0.07015 (8)	1.05091 (17)	0.41553 (7)	0.0727 (4)
O2	0.17099 (7)	0.92154 (18)	0.35786 (7)	0.0722 (4)
O3	0.00702 (6)	0.30330 (14)	0.69682 (6)	0.0564 (3)
O4	0.12332 (7)	0.14080 (15)	0.64271 (7)	0.0656 (4)
C2	0.11320 (9)	0.7786 (2)	0.45863 (8)	0.0516 (4)
C3	0.15832 (9)	0.6316 (2)	0.46040 (8)	0.0530 (4)
H3	0.2001	0.6062	0.4285	0.064*
C4	0.15041 (8)	0.3618 (2)	0.54858 (8)	0.0495 (4)
H4	0.1918	0.2997	0.5277	0.059*
C5	0.10882 (9)	0.2958 (2)	0.60783 (8)	0.0476 (4)
C6	0.04402 (8)	0.3882 (2)	0.63953 (8)	0.0453 (4)
C7	0.02331 (8)	0.5479 (2)	0.61286 (8)	0.0459 (4)
H7	−0.018	0.6096	0.634	0.055*
C8	0.06679 (8)	0.6150 (2)	0.55251 (8)	0.0448 (4)
C9	0.12971 (8)	0.5256 (2)	0.51953 (8)	0.0466 (4)
C10	0.11447 (10)	0.9300 (2)	0.41017 (9)	0.0556 (4)
C11	0.17434 (13)	1.0657 (4)	0.30566 (12)	0.0936 (8)
H11A	0.1271	1.0693	0.2763	0.14*
H11B	0.2184	1.0517	0.2725	0.14*
H11C	0.1797	1.1718	0.3335	0.14*
C12	0.18869 (10)	0.0457 (2)	0.61719 (11)	0.0661 (5)
H12A	0.1826	0.0201	0.5644	0.099*
H12B	0.1925	−0.0604	0.6452	0.099*
H12C	0.2354	0.1128	0.6246	0.099*
C13	−0.05334 (10)	0.3942 (2)	0.73565 (10)	0.0622 (5)
H13A	−0.0324	0.4989	0.7568	0.093*
H13B	−0.0737	0.3228	0.7755	0.093*
H13C	−0.0946	0.4221	0.7009	0.093*
H1	0.0202 (10)	0.852 (2)	0.5251 (10)	0.064 (5)*

	U11	U22	U33	U12	U13	U23
N	0.0517 (7)	0.0518 (8)	0.0492 (7)	−0.0002 (6)	0.0024 (6)	0.0013 (6)
O1	0.0850 (9)	0.0656 (9)	0.0676 (8)	0.0067 (7)	0.0120 (7)	0.0111 (6)
O2	0.0623 (7)	0.0919 (10)	0.0624 (7)	0.0005 (7)	0.0096 (6)	0.0236 (7)
O3	0.0601 (6)	0.0515 (7)	0.0576 (6)	0.0056 (5)	0.0185 (5)	0.0030 (5)
O4	0.0607 (7)	0.0554 (7)	0.0806 (8)	0.0140 (6)	0.0226 (6)	0.0125 (6)
C2	0.0472 (8)	0.0623 (10)	0.0454 (8)	−0.0074 (8)	−0.0004 (7)	0.0008 (7)
C3	0.0422 (8)	0.0693 (11)	0.0475 (8)	−0.0042 (8)	0.0021 (6)	0.0007 (8)
C4	0.0390 (7)	0.0577 (10)	0.0517 (8)	0.0014 (7)	0.0033 (6)	−0.0050 (8)
C5	0.0442 (8)	0.0465 (9)	0.0520 (8)	0.0006 (6)	0.0013 (6)	−0.0026 (7)
C6	0.0437 (7)	0.0482 (9)	0.0438 (7)	−0.0035 (7)	0.0026 (6)	−0.0036 (7)
C7	0.0435 (8)	0.0486 (9)	0.0457 (8)	0.0003 (7)	0.0029 (6)	−0.0069 (7)
C8	0.0431 (7)	0.0474 (8)	0.0438 (7)	−0.0037 (6)	−0.0037 (6)	−0.0030 (7)
C9	0.0375 (7)	0.0583 (10)	0.0441 (7)	−0.0041 (7)	−0.0016 (6)	−0.0028 (7)
C10	0.0522 (9)	0.0675 (11)	0.0470 (8)	−0.0070 (9)	−0.0033 (7)	0.0026 (8)
C11	0.0829 (14)	0.124 (2)	0.0739 (12)	−0.0071 (13)	0.0069 (11)	0.0451 (13)
C12	0.0582 (10)	0.0595 (11)	0.0806 (12)	0.0141 (9)	0.0098 (9)	0.0036 (9)
C13	0.0647 (10)	0.0622 (10)	0.0598 (10)	0.0076 (9)	0.0219 (8)	0.0008 (9)

N—C8	1.365 (2)	C4—H4	0.93
N—C2	1.3792 (19)	C5—C6	1.431 (2)
N—H1	0.926 (19)	C6—C7	1.367 (2)
O1—C10	1.206 (2)	C7—C8	1.399 (2)
O2—C10	1.338 (2)	C7—H7	0.93
O2—C11	1.447 (2)	C8—C9	1.404 (2)
O3—C6	1.3619 (18)	C11—H11A	0.96
O3—C13	1.4235 (19)	C11—H11B	0.96
O4—C5	1.3695 (19)	C11—H11C	0.96
O4—C12	1.410 (2)	C12—H12A	0.96
C2—C3	1.373 (2)	C12—H12B	0.96
C2—C10	1.449 (2)	C12—H12C	0.96
C3—C9	1.415 (2)	C13—H13A	0.96
C3—H3	0.93	C13—H13B	0.96
C4—C5	1.364 (2)	C13—H13C	0.96
C4—C9	1.410 (2)
C8—N—C2	108.82 (14)	C7—C8—C9	122.74 (14)
C8—N—H1	126.2 (11)	C8—C9—C4	118.80 (14)
C2—N—H1	125.0 (11)	C8—C9—C3	106.66 (14)
C10—O2—C11	115.57 (16)	C4—C9—C3	134.55 (14)
C6—O3—C13	117.19 (12)	O1—C10—O2	123.01 (16)
C5—O4—C12	117.03 (13)	O1—C10—C2	124.67 (15)
C3—C2—N	108.74 (14)	O2—C10—C2	112.32 (16)
C3—C2—C10	132.24 (14)	O2—C11—H11A	109.5
N—C2—C10	119.01 (15)	O2—C11—H11B	109.5
C2—C3—C9	107.56 (14)	H11A—C11—H11B	109.5
C2—C3—H3	126.2	O2—C11—H11C	109.5
C9—C3—H3	126.2	H11A—C11—H11C	109.5
C5—C4—C9	118.94 (14)	H11B—C11—H11C	109.5
C5—C4—H4	120.5	O4—C12—H12A	109.5
C9—C4—H4	120.5	O4—C12—H12B	109.5
C4—C5—O4	125.31 (14)	H12A—C12—H12B	109.5
C4—C5—C6	121.15 (15)	O4—C12—H12C	109.5
O4—C5—C6	113.54 (13)	H12A—C12—H12C	109.5
O3—C6—C7	124.82 (13)	H12B—C12—H12C	109.5
O3—C6—C5	114.20 (13)	O3—C13—H13A	109.5
C7—C6—C5	120.98 (14)	O3—C13—H13B	109.5
C6—C7—C8	117.36 (13)	H13A—C13—H13B	109.5
C6—C7—H7	121.3	O3—C13—H13C	109.5
C8—C7—H7	121.3	H13A—C13—H13C	109.5
N—C8—C7	129.03 (14)	H13B—C13—H13C	109.5
N—C8—C9	108.22 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···O1i	0.926 (19)	2.011 (19)	2.867 (2)	152.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H1⋯O1i	0.926 (19)	2.011 (19)	2.867 (2)	152.9 (16)

Symmetry code: (i) .