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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020199/av1060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020199/av1060Isup2.hkl
Contains datablock I

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
C14H11NO2Dx = 1.347 Mg m3
Mr = 225.25Cu Kα radiation, λ = 1.5418 Å
Monoclinic, P21/cCell parameters from 25 reflections
a = 7.573 (1) Åθ = 21–43°
b = 17.750 (1) ŵ = 0.74 mm1
c = 8.277 (1) ÅT = 298 K
β = 93.53 (1)°Rod-shaped, yellow
V = 1110.5 (2) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.015
ω/2θ scansθmax = 74.4°
Absorption correction: empirical (using intensity measurements)
(MolEN; Fair, 1990)
h = 90
Tmin = 0.731, Tmax = 0.863k = 022
2532 measured reflectionsl = 1010
2268 independent reflections3 standard reflections every 120 min
1833 reflections with F > 3σ(F) intensity decay: 1%
Refinement top
Refinement on FH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.061Weighting scheme based on measured s.u.'s
wR(F2) = 0.071(Δ/σ)max = 0.01
S = 0.87Δρmax = 0.45 e Å3
1833 reflectionsΔρmin = 0.34 e Å3
182 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3767 (3)0.0659 (1)0.3955 (3)0.0811 (5)
O20.3204 (2)0.0058 (1)0.6259 (2)0.0700 (4)
C10.0778 (4)0.1852 (2)0.4060 (3)0.0642 (6)
C20.0735 (4)0.1437 (2)0.4104 (3)0.0601 (5)
C30.1051 (3)0.0933 (1)0.5367 (3)0.0505 (5)
C40.0208 (3)0.0842 (1)0.6674 (3)0.0482 (4)
C4a0.1770 (3)0.1266 (1)0.6641 (3)0.0475 (4)
C50.3962 (4)0.0987 (2)0.9188 (3)0.0498 (5)
C5a0.3358 (3)0.1318 (1)0.7730 (3)0.0577 (5)
C60.5621 (4)0.1169 (2)0.9871 (3)0.0647 (6)
C70.6703 (4)0.1674 (2)0.9115 (4)0.0648 (6)
C80.6164 (4)0.2014 (2)0.7684 (3)0.0626 (6)
C8a0.4485 (3)0.1833 (1)0.7003 (3)0.0553 (5)
N90.3666 (3)0.2095 (1)0.5585 (3)0.0630 (5)
C9a0.2036 (4)0.1760 (1)0.5346 (3)0.0550 (5)
C100.0001 (4)0.0323 (2)0.8079 (3)0.0648 (6)
C110.2749 (3)0.0517 (1)0.5235 (3)0.0535 (5)
H10.498 (7)0.039 (3)0.398 (6)0.1902 (2)
H90.413 (4)0.247 (2)0.502 (4)0.1103 (9)
H110.0990.2180.3190.0761 (7)
H210.168 (4)0.145 (2)0.317 (3)0.0811 (7)
H510.325 (4)0.065 (2)0.977 (3)0.0811 (7)
H610.600 (4)0.094 (2)1.088 (4)0.0913 (8)
H710.777 (4)0.178 (2)0.960 (3)0.0811 (7)
H810.700 (4)0.238 (2)0.718 (4)0.0989 (8)
H1010.1020.0360.8800.0811
H1020.1020.0460.8630.0811
H1030.0130.0180.7700.0811
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.065 (1)0.105 (1)0.071 (1)0.019 (1)0.0157 (9)0.024 (1)
O20.063 (1)0.076 (1)0.070 (1)0.0162 (9)0.0041 (9)0.016 (1)
C10.075 (2)0.059 (1)0.058 (1)0.010 (1)0.006 (1)0.019 (1)
C20.067 (1)0.054 (1)0.058 (1)0.001 (1)0.007 (1)0.009 (1)
C30.052 (1)0.047 (1)0.053 (1)0.002 (1)0.002 (1)0.001 (1)
C40.052 (1)0.044 (1)0.049 (1)0.003 (1)0.006 (1)0.002 (1)
C4a0.053 (1)0.042 (1)0.047 (1)0.002 (1)0.003 (1)0.002 (1)
C50.060 (1)0.054 (1)0.058 (1)0.003 (1)0.002 (1)0.002 (1)
C5a0.053 (1)0.044 (1)0.052 (1)0.002 (1)0.004 (1)0.002 (1)
C60.066 (2)0.063 (1)0.064 (1)0.007 (1)0.008 (1)0.002 (1)
C70.055 (1)0.064 (1)0.074 (2)0.003 (1)0.005 (1)0.012 (1)
C80.058 (1)0.062 (1)0.067 (2)0.008 (1)0.003 (1)0.007 (1)
C8a0.059 (1)0.051 (1)0.057 (1)0.002 (1)0.004 (1)0.002 (1)
N90.067 (1)0.061 (1)0.060 (1)0.015 (1)0.000 (1)0.012 (1)
C9a0.061 (1)0.048 (1)0.056 (1)0.006 (1)0.002 (1)0.005 (1)
C100.060 (1)0.074 (2)0.060 (1)0.008 (1)0.001 (1)0.019 (1)
C110.053 (1)0.054 (1)0.053 (1)0.003 (1)0.000 (1)0.000 (1)
Geometric parameters (Å, º) top
C4a—C41.404 (3)O1—H11.03 (4)
C4a—C5a1.461 (3)N9—C8a1.376 (3)
C4a—C9a1.409 (3)N9—C9a1.373 (3)
C4—C31.406 (3)N9—H90.90 (4)
C4—C101.499 (4)C8a—C81.397 (4)
C3—C111.482 (4)C7—C81.369 (4)
C3—C21.408 (4)C7—C61.390 (4)
C5a—C8a1.410 (4)C7—H710.91 (3)
C5a—C51.394 (4)C8—H811.00 (3)
C11—O21.238 (3)C10—H1010.950
C11—O11.293 (3)C10—H1020.950
C1—C21.366 (4)C10—H1030.950
C1—C9a1.393 (4)C5—C61.384 (4)
C1—H110.950C5—H510.96 (3)
C2—H211.03 (3)C6—H610.96 (3)
C4—C4a—C5a133.2 (2)C8a—N9—C9a109.3 (2)
C4—C4a—C9a120.6 (2)C8a—N9—H9121 (2)
C5a—C4a—C9a106.2 (2)C9a—N9—H9130 (2)
C4a—C4—C3117.1 (2)C5a—C8a—N9109.3 (2)
C4a—C4—C10118.3 (2)C5a—C8a—C8122.5 (2)
C3—C4—C10124.6 (2)N9—C8a—C8128.2 (2)
C4—C3—C11123.0 (2)C4a—C9a—C1122.1 (2)
C4—C3—C2120.4 (2)C4a—C9a—N9109.2 (2)
C11—C3—C2116.6 (2)C1—C9a—N9128.7 (2)
C4a—C5a—C8a105.9 (2)C8—C7—C6121.4 (3)
C4a—C5a—C5136.2 (2)C8—C7—H71121 (2)
C8a—C5a—C5117.9 (2)C6—C7—H71118 (2)
C3—C11—O2123.6 (2)C8a—C8—C7117.6 (3)
C3—C11—O1115.5 (2)C8a—C8—H81123 (2)
O2—C11—O1120.8 (2)C7—C8—H81119 (2)
C2—C1—C9a116.9 (2)C4—C10—H101109.0
C2—C1—H11122.0C4—C10—H102109.7
C9a—C1—H11121.0C4—C10—H103109.7
C3—C2—C1122.9 (2)H101—C10—H102109.5
C3—C2—H21115 (2)H101—C10—H103109.5
C1—C2—H21122 (2)H102—C10—H103109.5
C11—O1—H1112.2 (2)C5a—C5—C6119.7 (2)
C5a—C5—H51122 (2)C7—C6—H61120 (2)
C6—C5—H51118 (2)C5—C6—H61119 (2)
C7—C6—C5120.9 (3)
C5a—C4a—C4—C3179.0 (2)C4—C3—C2—C10.6 (4)
C5a—C4a—C4—C100.7 (4)C11—C3—C2—C1179.4 (3)
C9a—C4a—C4—C30.2 (4)C4a—C5a—C8a—N90.9 (3)
C9a—C4a—C4—C10179.8 (2)C4a—C5a—C8a—C8178.4 (2)
C4—C4a—C5a—C8a178.4 (3)C5—C5a—C8a—N9179.8 (2)
C4—C4a—C5a—C50.1 (5)C5—C5a—C8a—C80.4 (4)
C9a—C4a—C5a—C8a0.8 (3)C4a—C5a—C5—C6178.5 (3)
C9a—C4a—C5a—C5179.3 (3)C8a—C5a—C5—C60.1 (4)
C4—C4a—C9a—C10.3 (4)C9a—C1—C2—C30.1 (4)
C4—C4a—C9a—N9178.9 (2)C2—C1—C9a—C4a0.3 (4)
C5a—C4a—C9a—C1179.6 (2)C2—C1—C9a—N9178.7 (3)
C5a—C4a—C9a—N90.4 (3)C9a—N9—C8a—C5a0.7 (3)
C4a—C4—C3—C11179.4 (2)C9a—N9—C8a—C8178.6 (3)
C4a—C4—C3—C20.6 (4)C8a—N9—C9a—C4a0.2 (3)
C10—C4—C3—C110.2 (4)C8a—N9—C9a—C1179.0 (3)
C10—C4—C3—C2179.9 (2)C5a—C8a—C8—C70.4 (4)
C4—C3—C11—O20.3 (4)N9—C8a—C8—C7179.6 (3)
C4—C3—C11—O1179.7 (2)C6—C7—C8—C8a0.2 (4)
C2—C3—C11—O2179.8 (2)C8—C7—C6—C50.7 (4)
C2—C3—C11—O10.3 (4)C5a—C5—C6—C70.6 (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-C4120.4 (2)109.9 (2)115.1 (2)114.7 (2)114.6 (5)110.5 (4)
C4-C4a-C5a133.2 (2)128.6 (2)127.5 (2)130.9 (2)130.4 (4)129.9 (4)
C3-C4-C4a117.1 (2)109.0 (2)114.6 (2)115.9 (2)116.5 (4)110.1 (4)
C1-C9a-N9128.7 (2)126.7 (2)127.5 (2)126.4 (2)126.8 (4)125.0 (3)
C4a-C5a-C5136.2 (2)134.7 (2)134.0 (3)134.7 (2)132.2 (4)133.6 (4)
C4-C4a-C9a120.6 (2)124.2 (3)124.5 (2)122.0 (2)121.5 (4)124.0 (4)
N9-C8a-C8128.2 (2)129.1 (2)129.4 (3)129.8 (2)131.0 (4)130.8 (4)
 

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