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The title compound, C15H17NO2, consists of a tetra­hydro­carbazole skeleton with a carboxy­ethyl group at position 3. Molecules are linked about inversion centres by N—H...O hydrogen bonds [N...O 2.908 (4) Å] to form centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018871/wn6121sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018871/wn6121Isup2.hkl
Contains datablock I

CCDC reference: 200771

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.115
  • Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6243 Proportion of unique data used 0.5894 Ratio reflections to parameters 9.4790
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I) top
Crystal data top
C15H17NO2F(000) = 520
Mr = 243.30Dx = 1.225 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.2221 (10) Åθ = 10–18°
b = 7.5133 (10) ŵ = 0.08 mm1
c = 17.539 (2) ÅT = 293 K
β = 101.603 (9)°Rod, colourless
V = 1319.5 (3) Å30.30 × 0.15 × 0.15 mm
Z = 4
Data collection top
Enraf Nonius CAD-4
diffractometer
653 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 26.3°, θmin = 2.4°
non–profiled ω scansh = 120
Absorption correction: ψ scan
(North et al., 1968)
k = 09
Tmin = 0.976, Tmax = 0.988l = 1821
2686 measured reflections3 standard reflections every 120 min
2686 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0459P)2]
where P = (Fo2 + 2Fc2)/3
1583 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0775 (3)0.6499 (3)0.17629 (14)0.1011 (11)
O20.2895 (4)0.6089 (3)0.23494 (18)0.0929 (11)
N90.0190 (4)0.7672 (4)0.5127 (2)0.0670 (11)
C10.1837 (4)0.7710 (4)0.44976 (19)0.0691 (12)
C20.2005 (4)0.7823 (4)0.36529 (18)0.0754 (12)
C30.1295 (4)0.6329 (4)0.31537 (19)0.0705 (13)
C40.0198 (4)0.6330 (5)0.3125 (2)0.0777 (14)
C4A0.0497 (4)0.6740 (4)0.3896 (2)0.0624 (13)
C50.3015 (5)0.6110 (5)0.3785 (3)0.0861 (15)
C5A0.1733 (4)0.6632 (4)0.4144 (2)0.0642 (12)
C60.4034 (5)0.6221 (6)0.4186 (3)0.1003 (18)
C70.3807 (5)0.6852 (5)0.4953 (4)0.1016 (16)
C80.2541 (6)0.7371 (5)0.5327 (2)0.0830 (14)
C8A0.1523 (5)0.7238 (4)0.4918 (3)0.0674 (13)
C9A0.0416 (4)0.7363 (4)0.4505 (2)0.0572 (12)
C100.1605 (5)0.6309 (5)0.2352 (2)0.0744 (15)
C110.3266 (5)0.6034 (5)0.1596 (2)0.0920 (16)
C120.4729 (4)0.5831 (6)0.1724 (3)0.1178 (19)
H1A0.23870.67580.47640.083*
H1B0.21150.88180.47650.083*
H2A0.16580.89550.34350.091*
H2B0.29490.77820.36410.091*
H30.16420.52120.34050.085*
H4A0.06210.72090.27500.093*
H4B0.05630.51730.29540.093*
H50.31790.56880.32760.103*
H60.48900.58710.39450.120*
H70.45140.69220.52130.122*
H80.23820.77940.58360.100*
H90.014 (4)0.805 (4)0.5572 (19)0.097 (16)*
H11A0.29930.71230.13110.110*
H11B0.28300.50400.12940.110*
H12A0.50000.57910.12310.177*
H12B0.49890.47470.20030.177*
H12C0.51510.68220.20210.177*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.126 (3)0.122 (2)0.0495 (15)0.0113 (18)0.0042 (19)0.0045 (14)
O20.104 (3)0.115 (2)0.060 (2)0.0009 (18)0.017 (3)0.0015 (15)
N90.088 (3)0.065 (2)0.047 (2)0.001 (2)0.009 (3)0.0025 (17)
C10.090 (3)0.061 (2)0.052 (2)0.004 (2)0.005 (3)0.0016 (17)
C20.088 (3)0.080 (3)0.057 (2)0.014 (2)0.009 (2)0.0052 (19)
C30.098 (3)0.066 (2)0.043 (2)0.004 (2)0.006 (3)0.0032 (18)
C40.090 (4)0.075 (2)0.061 (3)0.011 (2)0.000 (3)0.0052 (19)
C4A0.084 (3)0.053 (2)0.044 (2)0.005 (2)0.001 (3)0.0011 (17)
C50.087 (3)0.076 (3)0.091 (3)0.007 (3)0.008 (4)0.007 (2)
C5A0.073 (3)0.051 (2)0.064 (3)0.006 (2)0.003 (3)0.0044 (19)
C60.092 (4)0.084 (3)0.119 (5)0.001 (3)0.008 (4)0.007 (3)
C70.091 (4)0.073 (3)0.147 (5)0.009 (3)0.039 (4)0.015 (3)
C80.104 (4)0.058 (2)0.092 (3)0.007 (3)0.030 (4)0.003 (2)
C8A0.084 (4)0.046 (2)0.071 (3)0.009 (2)0.012 (3)0.005 (2)
C9A0.075 (3)0.052 (2)0.045 (2)0.002 (2)0.013 (3)0.0039 (18)
C100.108 (4)0.068 (2)0.046 (3)0.005 (3)0.013 (4)0.001 (2)
C110.132 (5)0.095 (3)0.054 (3)0.007 (3)0.030 (4)0.009 (2)
C120.112 (4)0.160 (4)0.090 (3)0.001 (3)0.039 (4)0.007 (3)
Geometric parameters (Å, º) top
C9A—C4A1.352 (4)C4—H4A0.9700
C9A—N91.378 (4)C4—H4B0.9700
C9A—C11.478 (4)C2—H2A0.9700
O2—C101.329 (4)C2—H2B0.9700
O2—C111.448 (4)C5A—C51.391 (5)
N9—C8A1.377 (5)C5—C61.372 (5)
N9—H90.84 (3)C5—H50.9300
C10—O11.206 (4)C11—C121.475 (5)
C10—C31.503 (5)C11—H11A0.9700
C1—C21.528 (4)C11—H11B0.9700
C1—H1A0.9700C7—C81.384 (5)
C1—H1B0.9700C7—C61.400 (5)
C3—C41.516 (5)C7—H70.9300
C3—C21.516 (4)C6—H60.9300
C3—H30.9800C8—H80.9300
C8A—C81.381 (5)C12—H12A0.9600
C8A—C5A1.407 (5)C12—H12B0.9600
C4A—C5A1.419 (5)C12—H12C0.9600
C4A—C41.477 (4)
C4A—C9A—N9109.6 (4)C3—C2—C1112.6 (3)
C4A—C9A—C1125.3 (4)C3—C2—H2A109.1
N9—C9A—C1125.1 (4)C1—C2—H2A109.1
C10—O2—C11116.7 (4)C3—C2—H2B109.1
C8A—N9—C9A109.2 (4)C1—C2—H2B109.1
C8A—N9—H9122 (3)H2A—C2—H2B107.8
C9A—N9—H9129 (3)C5—C5A—C8A118.4 (5)
O1—C10—O2122.6 (5)C5—C5A—C4A133.8 (4)
O1—C10—C3123.7 (5)C8A—C5A—C4A107.8 (4)
O2—C10—C3113.6 (4)C6—C5—C5A119.6 (4)
C9A—C1—C2108.7 (3)C6—C5—H5120.2
C9A—C1—H1A109.9C5A—C5—H5120.2
C2—C1—H1A109.9O2—C11—C12107.9 (4)
C9A—C1—H1B109.9O2—C11—H11A110.1
C2—C1—H1B109.9C12—C11—H11A110.1
H1A—C1—H1B108.3O2—C11—H11B110.1
C10—C3—C4111.7 (4)C12—C11—H11B110.1
C10—C3—C2112.4 (3)H11A—C11—H11B108.4
C4—C3—C2112.4 (3)C8—C7—C6120.6 (5)
C10—C3—H3106.6C8—C7—H7119.7
C4—C3—H3106.6C6—C7—H7119.7
C2—C3—H3106.6C5—C6—C7121.1 (5)
N9—C8A—C8130.8 (4)C5—C6—H6119.4
N9—C8A—C5A106.5 (4)C7—C6—H6119.4
C8—C8A—C5A122.7 (4)C8A—C8—C7117.6 (4)
C9A—C4A—C5A107.0 (4)C8A—C8—H8121.2
C9A—C4A—C4123.9 (5)C7—C8—H8121.2
C5A—C4A—C4129.1 (4)C11—C12—H12A109.5
C4A—C4—C3111.2 (4)C11—C12—H12B109.5
C4A—C4—H4A109.4H12A—C12—H12B109.5
C3—C4—H4A109.4C11—C12—H12C109.5
C4A—C4—H4B109.4H12A—C12—H12C109.5
C3—C4—H4B109.4H12B—C12—H12C109.5
H4A—C4—H4B108.0
C4A—C9A—N9—C8A0.2 (3)C10—C3—C2—C1172.7 (3)
C1—C9A—N9—C8A178.5 (3)C4—C3—C2—C160.3 (4)
C11—O2—C10—O11.8 (5)C9A—C1—C2—C346.1 (4)
C11—O2—C10—C3179.2 (3)N9—C8A—C5A—C5179.7 (3)
C4A—C9A—C1—C217.6 (4)C8—C8A—C5A—C51.5 (5)
N9—C9A—C1—C2160.4 (3)N9—C8A—C5A—C4A0.7 (3)
O1—C10—C3—C48.8 (5)C8—C8A—C5A—C4A177.4 (3)
O2—C10—C3—C4172.3 (3)C9A—C4A—C5A—C5179.5 (4)
O1—C10—C3—C2118.6 (4)C4—C4A—C5A—C51.3 (6)
O2—C10—C3—C260.4 (4)C9A—C4A—C5A—C8A0.8 (4)
C9A—N9—C8A—C8177.6 (3)C4—C4A—C5A—C8A177.4 (3)
C9A—N9—C8A—C5A0.4 (3)C8A—C5A—C5—C60.9 (5)
N9—C9A—C4A—C5A0.6 (4)C4A—C5A—C5—C6177.6 (4)
C1—C9A—C4A—C5A178.9 (3)C10—O2—C11—C12178.5 (3)
N9—C9A—C4A—C4177.7 (3)C5A—C5—C6—C70.0 (6)
C1—C9A—C4A—C40.6 (5)C8—C7—C6—C50.4 (6)
C9A—C4A—C4—C311.7 (4)N9—C8A—C8—C7178.8 (3)
C5A—C4A—C4—C3170.3 (3)C5A—C8A—C8—C71.1 (5)
C10—C3—C4—C4A167.7 (3)C6—C7—C8—C8A0.1 (5)
C2—C3—C4—C4A40.3 (4)
Table 2. Comparison of the bond angles (°) in the carbazole core of (I) with the corresponding values in the related compounds (II), (IX), (X) and (XII). top
Angles(I)(II)(IX)(X)(XII)
C2-C3-C4112.4 (3)119.4 (3)115.1 (2)114.7 (2)114.6 (5)
C4-C4A-C5A129.1 (4)133.6 (2)127.5 (2)130.9 (2)130.4 (4)
C3-C4-C4A111.2 (4)117.6 (2)114.6 (2)115.9 (2)116.5 (4)
C1-C9A-N9125.1 (4)128.7 (3)127.5 (2)126.4 (2)126.8 (4)
C4A-C5A-C5133.8 (4)135.1 (3)134.0 (3)134.7 (2)132.2 (4)
C4-C4A-C9A123.9 (5)120.8 (3)124.5 (2)122.0 (2)121.5 (4)
N9-C8A-C8130.8 (4)128.1 (3)129.4 (3)129.8 (2)131.0 (4)
 

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