organic compounds
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—HO hydrogen bonds [OO 2.620 (3) Å] to form centrosymmetric dimers.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020199/av1060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020199/av1060Isup2.hkl |
CCDC reference: 163907
Computing details top
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) top
Crystal data top
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) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 |
Data collection top
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 top
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.061 | Weighting scheme based on measured s.u.'s |
wR(F2) = 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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |
Comparison of the bond angles (°) in the carbazole core of (I) with the
corresponding values in the related compounds (IV), (V), (VI), (VIII) and (IX). top
Angles | (I) | (IV) | (V) | (VI) | (VIII) | (IX) |
C2-C3-C4 | 120.4 (2) | 109.9 (2) | 115.1 (2) | 114.7 (2) | 114.6 (5) | 110.5 (4) |
C4-C4a-C5a | 133.2 (2) | 128.6 (2) | 127.5 (2) | 130.9 (2) | 130.4 (4) | 129.9 (4) |
C3-C4-C4a | 117.1 (2) | 109.0 (2) | 114.6 (2) | 115.9 (2) | 116.5 (4) | 110.1 (4) |
C1-C9a-N9 | 128.7 (2) | 126.7 (2) | 127.5 (2) | 126.4 (2) | 126.8 (4) | 125.0 (3) |
C4a-C5a-C5 | 136.2 (2) | 134.7 (2) | 134.0 (3) | 134.7 (2) | 132.2 (4) | 133.6 (4) |
C4-C4a-C9a | 120.6 (2) | 124.2 (3) | 124.5 (2) | 122.0 (2) | 121.5 (4) | 124.0 (4) |
N9-C8a-C8 | 128.2 (2) | 129.1 (2) | 129.4 (3) | 129.8 (2) | 131.0 (4) | 130.8 (4) |