4-Methylcarbazole-3-carboxylic acid

The title compound, C₁₄H₁₁NO₂, consists of a carbazole skeleton with carboxyl­ic acid and methyl groups at positions 3 and 4, respectively. Molecules are linked about inversion centres by O—H...O hydrogen bonds [O...O 2.620 (3) Å] to form centrosymmetric dimers.

Computing details

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: MolEN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: MolEN.

(I)

Crystal data

C14H11NO2	Dx = 1.347 Mg m^−3
Mr = 225.25	Cu Kα radiation, λ = 1.5418 Å
Monoclinic, P21/c	Cell parameters from 25 reflections
a = 7.573 (1) Å	θ = 21–43°
b = 17.750 (1) Å	µ = 0.74 mm^−1
c = 8.277 (1) Å	T = 298 K
β = 93.53 (1)°	Rod-shaped, yellow
V = 1110.5 (2) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.015
ω/2θ scans	θmax = 74.4°
Absorption correction: empirical (using intensity measurements) (MolEN; Fair, 1990)	h = −9→0
Tmin = 0.731, Tmax = 0.863	k = 0→22
2532 measured reflections	l = −10→10
2268 independent reflections	3 standard reflections every 120 min
1833 reflections with F > 3σ(F)	intensity decay: 1%

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.061	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.071	(Δ/σ)max = 0.01
S = 0.87	Δρmax = 0.45 e Å^−3
1833 reflections	Δρmin = −0.34 e Å^−3
182 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.3767 (3)	0.0659 (1)	0.3955 (3)	0.0811 (5)
O2	−0.3204 (2)	0.0058 (1)	0.6259 (2)	0.0700 (4)
C1	0.0778 (4)	0.1852 (2)	0.4060 (3)	0.0642 (6)
C2	−0.0735 (4)	0.1437 (2)	0.4104 (3)	0.0601 (5)
C3	−0.1051 (3)	0.0933 (1)	0.5367 (3)	0.0505 (5)
C4	0.0208 (3)	0.0842 (1)	0.6674 (3)	0.0482 (4)
C4a	0.1770 (3)	0.1266 (1)	0.6641 (3)	0.0475 (4)
C5	0.3962 (4)	0.0987 (2)	0.9188 (3)	0.0498 (5)
C5a	0.3358 (3)	0.1318 (1)	0.7730 (3)	0.0577 (5)
C6	0.5621 (4)	0.1169 (2)	0.9871 (3)	0.0647 (6)
C7	0.6703 (4)	0.1674 (2)	0.9115 (4)	0.0648 (6)
C8	0.6164 (4)	0.2014 (2)	0.7684 (3)	0.0626 (6)
C8a	0.4485 (3)	0.1833 (1)	0.7003 (3)	0.0553 (5)
N9	0.3666 (3)	0.2095 (1)	0.5585 (3)	0.0630 (5)
C9a	0.2036 (4)	0.1760 (1)	0.5346 (3)	0.0550 (5)
C10	−0.0001 (4)	0.0323 (2)	0.8079 (3)	0.0648 (6)
C11	−0.2749 (3)	0.0517 (1)	0.5235 (3)	0.0535 (5)
H1	−0.498 (7)	0.039 (3)	0.398 (6)	0.1902 (2)
H9	0.413 (4)	0.247 (2)	0.502 (4)	0.1103 (9)
H11	0.099	0.218	0.319	0.0761 (7)
H21	−0.168 (4)	0.145 (2)	0.317 (3)	0.0811 (7)
H51	0.325 (4)	0.065 (2)	0.977 (3)	0.0811 (7)
H61	0.600 (4)	0.094 (2)	1.088 (4)	0.0913 (8)
H71	0.777 (4)	0.178 (2)	0.960 (3)	0.0811 (7)
H81	0.700 (4)	0.238 (2)	0.718 (4)	0.0989 (8)
H101	0.102	0.036	0.880	0.0811
H102	−0.102	0.046	0.863	0.0811
H103	−0.013	−0.018	0.770	0.0811

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.065 (1)	0.105 (1)	0.071 (1)	−0.019 (1)	−0.0157 (9)	0.024 (1)
O2	0.063 (1)	0.076 (1)	0.070 (1)	−0.0162 (9)	−0.0041 (9)	0.016 (1)
C1	0.075 (2)	0.059 (1)	0.058 (1)	−0.010 (1)	−0.006 (1)	0.019 (1)
C2	0.067 (1)	0.054 (1)	0.058 (1)	−0.001 (1)	−0.007 (1)	0.009 (1)
C3	0.052 (1)	0.047 (1)	0.053 (1)	0.002 (1)	0.002 (1)	0.001 (1)
C4	0.052 (1)	0.044 (1)	0.049 (1)	0.003 (1)	0.006 (1)	0.002 (1)
C4a	0.053 (1)	0.042 (1)	0.047 (1)	0.002 (1)	0.003 (1)	0.002 (1)
C5	0.060 (1)	0.054 (1)	0.058 (1)	0.003 (1)	−0.002 (1)	0.002 (1)
C5a	0.053 (1)	0.044 (1)	0.052 (1)	0.002 (1)	0.004 (1)	−0.002 (1)
C6	0.066 (2)	0.063 (1)	0.064 (1)	0.007 (1)	−0.008 (1)	−0.002 (1)
C7	0.055 (1)	0.064 (1)	0.074 (2)	0.003 (1)	−0.005 (1)	−0.012 (1)
C8	0.058 (1)	0.062 (1)	0.067 (2)	−0.008 (1)	0.003 (1)	−0.007 (1)
C8a	0.059 (1)	0.051 (1)	0.057 (1)	−0.002 (1)	0.004 (1)	−0.002 (1)
N9	0.067 (1)	0.061 (1)	0.060 (1)	−0.015 (1)	−0.000 (1)	0.012 (1)
C9a	0.061 (1)	0.048 (1)	0.056 (1)	−0.006 (1)	0.002 (1)	0.005 (1)
C10	0.060 (1)	0.074 (2)	0.060 (1)	−0.008 (1)	0.001 (1)	0.019 (1)
C11	0.053 (1)	0.054 (1)	0.053 (1)	0.003 (1)	0.000 (1)	−0.000 (1)

Geometric parameters (Å, º)

C4a—C4	1.404 (3)	O1—H1	1.03 (4)
C4a—C5a	1.461 (3)	N9—C8a	1.376 (3)
C4a—C9a	1.409 (3)	N9—C9a	1.373 (3)
C4—C3	1.406 (3)	N9—H9	0.90 (4)
C4—C10	1.499 (4)	C8a—C8	1.397 (4)
C3—C11	1.482 (4)	C7—C8	1.369 (4)
C3—C2	1.408 (4)	C7—C6	1.390 (4)
C5a—C8a	1.410 (4)	C7—H71	0.91 (3)
C5a—C5	1.394 (4)	C8—H81	1.00 (3)
C11—O2	1.238 (3)	C10—H101	0.950
C11—O1	1.293 (3)	C10—H102	0.950
C1—C2	1.366 (4)	C10—H103	0.950
C1—C9a	1.393 (4)	C5—C6	1.384 (4)
C1—H11	0.950	C5—H51	0.96 (3)
C2—H21	1.03 (3)	C6—H61	0.96 (3)
C4—C4a—C5a	133.2 (2)	C8a—N9—C9a	109.3 (2)
C4—C4a—C9a	120.6 (2)	C8a—N9—H9	121 (2)
C5a—C4a—C9a	106.2 (2)	C9a—N9—H9	130 (2)
C4a—C4—C3	117.1 (2)	C5a—C8a—N9	109.3 (2)
C4a—C4—C10	118.3 (2)	C5a—C8a—C8	122.5 (2)
C3—C4—C10	124.6 (2)	N9—C8a—C8	128.2 (2)
C4—C3—C11	123.0 (2)	C4a—C9a—C1	122.1 (2)
C4—C3—C2	120.4 (2)	C4a—C9a—N9	109.2 (2)
C11—C3—C2	116.6 (2)	C1—C9a—N9	128.7 (2)
C4a—C5a—C8a	105.9 (2)	C8—C7—C6	121.4 (3)
C4a—C5a—C5	136.2 (2)	C8—C7—H71	121 (2)
C8a—C5a—C5	117.9 (2)	C6—C7—H71	118 (2)
C3—C11—O2	123.6 (2)	C8a—C8—C7	117.6 (3)
C3—C11—O1	115.5 (2)	C8a—C8—H81	123 (2)
O2—C11—O1	120.8 (2)	C7—C8—H81	119 (2)
C2—C1—C9a	116.9 (2)	C4—C10—H101	109.0
C2—C1—H11	122.0	C4—C10—H102	109.7
C9a—C1—H11	121.0	C4—C10—H103	109.7
C3—C2—C1	122.9 (2)	H101—C10—H102	109.5
C3—C2—H21	115 (2)	H101—C10—H103	109.5
C1—C2—H21	122 (2)	H102—C10—H103	109.5
C11—O1—H1	112.2 (2)	C5a—C5—C6	119.7 (2)
C5a—C5—H51	122 (2)	C7—C6—H61	120 (2)
C6—C5—H51	118 (2)	C5—C6—H61	119 (2)
C7—C6—C5	120.9 (3)
C5a—C4a—C4—C3	−179.0 (2)	C4—C3—C2—C1	0.6 (4)
C5a—C4a—C4—C10	0.7 (4)	C11—C3—C2—C1	−179.4 (3)
C9a—C4a—C4—C3	0.2 (4)	C4a—C5a—C8a—N9	0.9 (3)
C9a—C4a—C4—C10	179.8 (2)	C4a—C5a—C8a—C8	−178.4 (2)
C4—C4a—C5a—C8a	178.4 (3)	C5—C5a—C8a—N9	179.8 (2)
C4—C4a—C5a—C5	−0.1 (5)	C5—C5a—C8a—C8	0.4 (4)
C9a—C4a—C5a—C8a	−0.8 (3)	C4a—C5a—C5—C6	178.5 (3)
C9a—C4a—C5a—C5	−179.3 (3)	C8a—C5a—C5—C6	0.1 (4)
C4—C4a—C9a—C1	0.3 (4)	C9a—C1—C2—C3	−0.1 (4)
C4—C4a—C9a—N9	−178.9 (2)	C2—C1—C9a—C4a	−0.3 (4)
C5a—C4a—C9a—C1	179.6 (2)	C2—C1—C9a—N9	178.7 (3)
C5a—C4a—C9a—N9	0.4 (3)	C9a—N9—C8a—C5a	−0.7 (3)
C4a—C4—C3—C11	179.4 (2)	C9a—N9—C8a—C8	178.6 (3)
C4a—C4—C3—C2	−0.6 (4)	C8a—N9—C9a—C4a	0.2 (3)
C10—C4—C3—C11	−0.2 (4)	C8a—N9—C9a—C1	−179.0 (3)
C10—C4—C3—C2	179.9 (2)	C5a—C8a—C8—C7	−0.4 (4)
C4—C3—C11—O2	0.3 (4)	N9—C8a—C8—C7	−179.6 (3)
C4—C3—C11—O1	−179.7 (2)	C6—C7—C8—C8a	−0.2 (4)
C2—C3—C11—O2	−179.8 (2)	C8—C7—C6—C5	0.7 (4)
C2—C3—C11—O1	0.3 (4)	C5a—C5—C6—C7	−0.6 (4)