Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035660/wn2176sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035660/wn2176Isup2.hkl |
CCDC reference: 657857
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.067
- wR factor = 0.221
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 0.804 Test value = 0.800
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.80 e/A PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9A - C41 ... 1.38 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2A = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Gunaseelan et al. (2007a,b); Thiruvalluvar et al. (2007).
A mixture of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetate (270 mg, 0.001 mol), glass powder (500 mg) and iron powder (500 mg) in diphenyl ether (15 ml) was heated at 443–473 K for 30 min. Carbon monoxide was liberated during heating. After cooling, the mixture was extracted with ethyl acetate and purified by column chromatography over silica gel using petroleum ether/ethyl acetate (95:5 v/v) as eluant to obtain the pure title compound (100 mg, 40%), which was recrystallized from glacial acetic acid.
Atoms C2A, C3A, C4A of the cyclohexene ring, with attached hydrogen atoms, and all atoms of the ester group are disordered over two positions; the site occupancy factors refined to 0.879 (3) and 0.121 (3). All H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H = 0.87 Å, C—H = 0.94–0.99 Å and Uiso(H) = xUeq(parent atom), where x = 1.2 or 1.5.
The title compound, has been analysed as part of our crystallographic studies on substituted carbazoles (Gunaseelan et al. (2007a, b); Thiruvalluvar et al. (2007)).
The molecular structure of the title compound, with the atomic numbering scheme, is shown in Fig. 1. The dihedral angle between the benzene ring and the fused pyrrole ring is 1.0 (1)°. The cyclohexene ring adopts a twist conformation. The crystal structure is stabilized by intermolecular N9—H9···O1(-x + 1,-y + 1,-z) and C14A—H14B···O2A(-x + 1,-y + 1,-z + 1) hydrogen bonds (Fig. 2).
For related literature, see: Gunaseelan et al. (2007a,b); Thiruvalluvar et al. (2007).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C14H13NO3 | Z = 2 |
Mr = 243.25 | F(000) = 256 |
Triclinic, P1 | Dx = 1.380 Mg m−3 |
Hall symbol: -P 1 | Melting point: 409(1) K |
a = 6.9814 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1303 (13) Å | Cell parameters from 2541 reflections |
c = 10.780 (2) Å | θ = 4.8–30.6° |
α = 88.575 (14)° | µ = 0.10 mm−1 |
β = 76.881 (15)° | T = 203 K |
γ = 79.367 (14)° | Plate, light-brown |
V = 585.59 (18) Å3 | 0.36 × 0.31 × 0.22 mm |
Oxford Diffraction Gemini diffractometer | 3176 independent reflections |
Radiation source: fine-focus sealed tube | 1673 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 30.7°, θmin = 4.8° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −11→11 |
Tmin = 0.890, Tmax = 1.000 | l = −12→14 |
6572 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1197P)2] where P = (Fo2 + 2Fc2)/3 |
3176 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.80 e Å−3 |
6 restraints | Δρmin = −0.44 e Å−3 |
C14H13NO3 | γ = 79.367 (14)° |
Mr = 243.25 | V = 585.59 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9814 (12) Å | Mo Kα radiation |
b = 8.1303 (13) Å | µ = 0.10 mm−1 |
c = 10.780 (2) Å | T = 203 K |
α = 88.575 (14)° | 0.36 × 0.31 × 0.22 mm |
β = 76.881 (15)° |
Oxford Diffraction Gemini diffractometer | 3176 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1673 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 1.000 | Rint = 0.023 |
6572 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 6 restraints |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.80 e Å−3 |
3176 reflections | Δρmin = −0.44 e Å−3 |
176 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.2838 (3) | 0.6953 (3) | 0.1859 (2) | 0.0373 (5) | |
O1 | 0.4523 (2) | 0.6125 (2) | 0.17505 (15) | 0.0468 (5) | |
C5 | −0.2646 (3) | 0.8206 (3) | −0.0495 (2) | 0.0478 (6) | |
H5 | −0.3758 | 0.8873 | 0.0038 | 0.057* | |
C6 | −0.2759 (4) | 0.7722 (3) | −0.1673 (3) | 0.0521 (7) | |
H6 | −0.3949 | 0.8067 | −0.1952 | 0.063* | |
C7 | −0.1117 (4) | 0.6713 (3) | −0.2474 (2) | 0.0493 (6) | |
H7 | −0.1228 | 0.6397 | −0.3284 | 0.059* | |
C8 | 0.0649 (3) | 0.6177 (3) | −0.2100 (2) | 0.0412 (6) | |
H8 | 0.1742 | 0.5498 | −0.2640 | 0.049* | |
C8A | 0.0767 (3) | 0.6671 (3) | −0.0902 (2) | 0.0348 (5) | |
N9 | 0.2302 (2) | 0.6317 (2) | −0.02795 (16) | 0.0356 (5) | |
H9 | 0.3471 | 0.5707 | −0.0583 | 0.043* | |
C9A | 0.1692 (3) | 0.7085 (3) | 0.0902 (2) | 0.0357 (5) | |
C41 | −0.0244 (3) | 0.7963 (3) | 0.1053 (2) | 0.0376 (5) | |
C42 | −0.0870 (3) | 0.7707 (3) | −0.0082 (2) | 0.0362 (5) | |
C13 | 0.2754 (3) | 0.7454 (3) | 0.4124 (2) | 0.0490 (7) | |
C2A | 0.1862 (4) | 0.8086 (4) | 0.3039 (3) | 0.0398 (7) | 0.879 (3) |
H2A | 0.2226 | 0.9198 | 0.2832 | 0.048* | 0.879 (3) |
C3A | −0.0392 (4) | 0.8347 (4) | 0.3339 (3) | 0.0579 (8) | 0.879 (3) |
H31A | −0.0801 | 0.7290 | 0.3642 | 0.069* | 0.879 (3) |
H31B | −0.0918 | 0.9171 | 0.4037 | 0.069* | 0.879 (3) |
C4A | −0.1345 (4) | 0.8929 (3) | 0.2245 (2) | 0.0503 (7) | 0.879 (3) |
H4A | −0.2742 | 0.8778 | 0.2451 | 0.060* | 0.879 (3) |
H4B | −0.1330 | 1.0124 | 0.2112 | 0.060* | 0.879 (3) |
O2A | 0.2322 (3) | 0.6162 (2) | 0.47104 (18) | 0.0558 (6) | 0.879 (3) |
O3A | 0.3986 (3) | 0.8286 (3) | 0.4441 (2) | 0.0502 (6) | 0.879 (3) |
C14A | 0.4832 (4) | 0.7645 (4) | 0.5509 (3) | 0.0583 (7) | 0.879 (3) |
H14A | 0.5682 | 0.8382 | 0.5692 | 0.087* | 0.879 (3) |
H14B | 0.5618 | 0.6533 | 0.5297 | 0.087* | 0.879 (3) |
H14C | 0.3760 | 0.7591 | 0.6252 | 0.087* | 0.879 (3) |
C2B | 0.146 (3) | 0.742 (3) | 0.325 (2) | 0.0398 (7) | 0.121 (3) |
H2B | 0.1077 | 0.6313 | 0.3477 | 0.048* | 0.121 (3) |
C3B | −0.0392 (4) | 0.8347 (4) | 0.3339 (3) | 0.0579 (8) | 0.121 (3) |
H32A | −0.0423 | 0.9362 | 0.3819 | 0.069* | 0.121 (3) |
H32B | −0.1319 | 0.7723 | 0.3890 | 0.069* | 0.121 (3) |
C4B | −0.1345 (4) | 0.8929 (3) | 0.2245 (2) | 0.0503 (7) | 0.121 (3) |
H41 | −0.2742 | 0.8778 | 0.2451 | 0.060* | 0.121 (3) |
H42 | −0.1330 | 1.0124 | 0.2112 | 0.060* | 0.121 (3) |
O2B | 0.347 (2) | 0.8761 (13) | 0.3797 (16) | 0.0558 (6) | 0.121 (3) |
O3B | 0.3399 (16) | 0.6820 (11) | 0.5095 (8) | 0.0502 (6) | 0.121 (3) |
C14B | 0.4832 (4) | 0.7645 (4) | 0.5509 (3) | 0.0583 (7) | 0.121 (3) |
H14D | 0.4959 | 0.7267 | 0.6353 | 0.087* | 0.121 (3) |
H14E | 0.4370 | 0.8847 | 0.5535 | 0.087* | 0.121 (3) |
H14F | 0.6123 | 0.7370 | 0.4917 | 0.087* | 0.121 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0329 (11) | 0.0413 (12) | 0.0319 (12) | −0.0019 (9) | 0.0017 (9) | −0.0063 (9) |
O1 | 0.0336 (8) | 0.0562 (10) | 0.0431 (10) | 0.0059 (7) | −0.0037 (7) | −0.0127 (8) |
C5 | 0.0379 (12) | 0.0466 (14) | 0.0535 (16) | 0.0005 (10) | −0.0071 (11) | 0.0114 (11) |
C6 | 0.0425 (13) | 0.0549 (15) | 0.0598 (17) | −0.0063 (12) | −0.0172 (12) | 0.0173 (13) |
C7 | 0.0574 (15) | 0.0525 (14) | 0.0437 (14) | −0.0184 (12) | −0.0173 (11) | 0.0063 (11) |
C8 | 0.0435 (12) | 0.0370 (12) | 0.0412 (13) | −0.0080 (10) | −0.0058 (10) | 0.0030 (10) |
C8A | 0.0357 (11) | 0.0313 (11) | 0.0358 (12) | −0.0073 (8) | −0.0041 (9) | 0.0040 (9) |
N9 | 0.0281 (9) | 0.0399 (10) | 0.0341 (10) | −0.0007 (7) | −0.0009 (7) | −0.0058 (8) |
C9A | 0.0332 (11) | 0.0326 (11) | 0.0366 (12) | −0.0026 (9) | −0.0009 (9) | −0.0033 (9) |
C41 | 0.0324 (11) | 0.0320 (11) | 0.0404 (12) | 0.0035 (8) | 0.0009 (9) | −0.0019 (9) |
C42 | 0.0328 (11) | 0.0319 (11) | 0.0392 (12) | −0.0011 (8) | −0.0030 (9) | 0.0060 (9) |
C13 | 0.0426 (13) | 0.0516 (15) | 0.0446 (14) | −0.0052 (11) | 0.0066 (10) | −0.0231 (12) |
C2A | 0.0448 (15) | 0.0333 (15) | 0.0356 (14) | −0.0027 (12) | −0.0004 (11) | −0.0086 (12) |
C3A | 0.0425 (13) | 0.0701 (18) | 0.0487 (15) | 0.0139 (12) | −0.0021 (11) | −0.0228 (13) |
C4A | 0.0436 (13) | 0.0478 (14) | 0.0471 (15) | 0.0086 (11) | 0.0021 (11) | −0.0067 (11) |
O2A | 0.0706 (14) | 0.0513 (12) | 0.0476 (12) | −0.0167 (10) | −0.0134 (10) | 0.0046 (10) |
O3A | 0.0525 (12) | 0.0491 (11) | 0.0515 (13) | −0.0132 (9) | −0.0128 (9) | −0.0048 (10) |
C14A | 0.0597 (16) | 0.0636 (17) | 0.0539 (16) | −0.0092 (13) | −0.0189 (13) | −0.0027 (13) |
C2B | 0.0448 (15) | 0.0333 (15) | 0.0356 (14) | −0.0027 (12) | −0.0004 (11) | −0.0086 (12) |
C3B | 0.0425 (13) | 0.0701 (18) | 0.0487 (15) | 0.0139 (12) | −0.0021 (11) | −0.0228 (13) |
C4B | 0.0436 (13) | 0.0478 (14) | 0.0471 (15) | 0.0086 (11) | 0.0021 (11) | −0.0067 (11) |
O2B | 0.0706 (14) | 0.0513 (12) | 0.0476 (12) | −0.0167 (10) | −0.0134 (10) | 0.0046 (10) |
O3B | 0.0525 (12) | 0.0491 (11) | 0.0515 (13) | −0.0132 (9) | −0.0128 (9) | −0.0048 (10) |
C14B | 0.0597 (16) | 0.0636 (17) | 0.0539 (16) | −0.0092 (13) | −0.0189 (13) | −0.0027 (13) |
O1—C1 | 1.225 (3) | C8—C8A | 1.386 (3) |
O2A—C13 | 1.262 (3) | C8A—C42 | 1.422 (3) |
O2B—C13 | 1.265 (12) | C9A—C41 | 1.383 (3) |
O3A—C13 | 1.293 (3) | C41—C42 | 1.422 (3) |
O3A—C14A | 1.454 (4) | C2A—H2A | 0.9900 |
O3B—C13 | 1.290 (10) | C2B—H2B | 0.9900 |
O3B—C14B | 1.455 (11) | C3A—H31A | 0.9800 |
N9—C8A | 1.373 (3) | C3A—H31B | 0.9800 |
N9—C9A | 1.374 (3) | C3B—H32A | 0.9800 |
N9—H9 | 0.8700 | C3B—H32B | 0.9800 |
C1—C2B | 1.60 (2) | C4A—H4A | 0.9800 |
C1—C2A | 1.538 (4) | C4A—H4B | 0.9800 |
C1—C9A | 1.433 (3) | C4B—H41 | 0.9800 |
C2A—C13 | 1.485 (4) | C4B—H42 | 0.9800 |
C2A—C3A | 1.508 (4) | C5—H5 | 0.9400 |
C2B—C3B | 1.36 (2) | C6—H6 | 0.9400 |
C2B—C13 | 1.45 (2) | C7—H7 | 0.9400 |
C3A—C4A | 1.506 (4) | C8—H8 | 0.9400 |
C3B—C4B | 1.506 (4) | C14A—H14B | 0.9700 |
C4A—C41 | 1.497 (3) | C14A—H14C | 0.9700 |
C4B—C41 | 1.497 (3) | C14A—H14A | 0.9700 |
C5—C42 | 1.398 (3) | C14B—H14D | 0.9700 |
C5—C6 | 1.362 (4) | C14B—H14E | 0.9700 |
C6—C7 | 1.404 (4) | C14B—H14F | 0.9700 |
C7—C8 | 1.376 (4) | ||
O1···O2A | 3.210 (3) | C9A···H31A | 3.0600 |
O1···N9 | 2.941 (2) | C14A···H6xiii | 3.0900 |
O1···C5i | 3.389 (3) | C14B···H6xiii | 3.0900 |
O1···O2B | 2.986 (14) | C14B···H32Bi | 2.8600 |
O1···N9ii | 2.883 (2) | C42···H4Bxi | 3.0900 |
O2A···C8iii | 3.371 (3) | C42···H42xi | 3.0900 |
O2A···C14Aiv | 3.337 (3) | H2A···C6xi | 2.8200 |
O2A···O1 | 3.210 (3) | H2B···C7vii | 2.7000 |
O2A···C7iii | 3.397 (4) | H2B···C3A | 1.8000 |
O2B···O1 | 2.986 (14) | H2B···C4A | 2.9500 |
O3B···C8iii | 3.280 (10) | H2B···H7vii | 2.2000 |
O1···H9ii | 2.0700 | H4A···O3Aviii | 2.8400 |
O1···H9 | 2.8200 | H4B···C8Axi | 2.9400 |
O2A···H8iii | 2.8400 | H4B···C42xi | 3.0900 |
O2A···H31A | 2.7000 | H5···C5x | 3.0800 |
O2A···H14B | 2.5900 | H5···H5x | 2.2900 |
O2A···H14C | 2.5300 | H6···C14Bxii | 3.0900 |
O2A···H14Biv | 2.3900 | H6···H14Dxii | 2.2800 |
O2A···H7iii | 2.8800 | H6···C14Axii | 3.0900 |
O2B···H14Ev | 2.8700 | H7···O2Aix | 2.8800 |
O2B···H14F | 2.5200 | H7···H2Bvii | 2.2000 |
O2B···H14E | 2.1100 | H8···O3Bix | 2.7400 |
O2B···H32A | 2.6700 | H8···O2Aix | 2.8400 |
O2B···H41i | 2.7200 | H8···H14Cix | 2.5200 |
O3A···H31Bvi | 2.9100 | H9···O1 | 2.8200 |
O3A···H14Av | 2.7600 | H9···O1ii | 2.0700 |
O3A···H4Ai | 2.8400 | H14A···O3Av | 2.7600 |
O3B···H8iii | 2.7400 | H14B···O2A | 2.5900 |
N9···O1ii | 2.883 (2) | H14B···O2Aiv | 2.3900 |
N9···O1 | 2.941 (2) | H14C···O2A | 2.5300 |
C1···C7vii | 3.410 (4) | H14C···C8iii | 2.8700 |
C2B···C7vii | 3.55 (2) | H14C···H8iii | 2.5200 |
C2B···C4A | 2.55 (2) | H14D···C6xiii | 3.0000 |
C5···O1viii | 3.389 (3) | H14D···H6xiii | 2.2800 |
C7···C1vii | 3.410 (4) | H14E···O2B | 2.1100 |
C7···C9Avii | 3.529 (4) | H14E···O2Bv | 2.8700 |
C7···O2Aix | 3.397 (4) | H14E···H14Ev | 2.3800 |
C7···C2Bvii | 3.55 (2) | H14F···H32Bi | 1.9400 |
C8···C9Avii | 3.442 (3) | H14F···C3Bi | 2.8700 |
C8···O2Aix | 3.371 (3) | H14F···O2B | 2.5200 |
C8···C41vii | 3.564 (3) | H31A···O2A | 2.7000 |
C8···O3Bix | 3.280 (10) | H31A···C9A | 3.0600 |
C8A···C8Avii | 3.490 (3) | H31B···O3Avi | 2.9100 |
C9A···C8vii | 3.442 (3) | H32A···O2B | 2.6700 |
C9A···C7vii | 3.529 (4) | H32A···C4A | 2.0100 |
C14A···O2Aiv | 3.337 (3) | H32A···H4A | 2.5300 |
C41···C8vii | 3.564 (3) | H32A···H4B | 2.1200 |
C2B···H4B | 3.0800 | H32B···C4A | 2.0100 |
C3B···H4B | 2.0500 | H32B···C14Bviii | 2.8600 |
C3B···H4A | 2.0500 | H32B···H14Fviii | 1.9400 |
C3B···H14Fviii | 2.8700 | H32B···H4A | 2.1100 |
C5···H5x | 3.0800 | H41···O2Bviii | 2.7200 |
C6···H2Axi | 2.8200 | H41···C3A | 2.0500 |
C6···H14Dxii | 3.0000 | H41···H4B | 1.5900 |
C7···H2Bvii | 2.7000 | H42···C3A | 2.0500 |
C8···H14Cix | 2.8700 | H42···H4A | 1.5900 |
C8A···H4Bxi | 2.9400 | H42···C8Axi | 2.9400 |
C8A···H42xi | 2.9400 | H42···C42xi | 3.0900 |
C13—O3A—C14A | 116.0 (2) | C3A—C2A—H2A | 107.00 |
C13—O3B—C14B | 116.2 (7) | C13—C2A—H2A | 107.00 |
C8A—N9—C9A | 108.92 (17) | C13—C2B—H2B | 99.00 |
C9A—N9—H9 | 126.00 | C3B—C2B—H2B | 99.00 |
C8A—N9—H9 | 126.00 | C1—C2B—H2B | 99.00 |
O1—C1—C2A | 120.4 (2) | C2A—C3A—H31A | 108.00 |
O1—C1—C9A | 125.0 (2) | C2A—C3A—H31B | 108.00 |
C2A—C1—C9A | 114.4 (2) | H31A—C3A—H31B | 107.00 |
O1—C1—C2B | 119.4 (8) | C4A—C3A—H31A | 108.00 |
C2B—C1—C9A | 112.2 (8) | C4A—C3A—H31B | 108.00 |
C1—C2A—C13 | 109.7 (2) | C2B—C3B—H32A | 106.00 |
C3A—C2A—C13 | 113.9 (2) | C2B—C3B—H32B | 106.00 |
C1—C2A—C3A | 112.7 (2) | C4B—C3B—H32A | 106.00 |
C3B—C2B—C13 | 126.8 (16) | C4B—C3B—H32B | 106.00 |
C1—C2B—C3B | 118.0 (14) | H32A—C3B—H32B | 106.00 |
C1—C2B—C13 | 108.2 (14) | C3A—C4A—H4A | 110.00 |
C2A—C3A—C4A | 115.4 (2) | C41—C4A—H4A | 110.00 |
C2B—C3B—C4B | 126.3 (9) | C41—C4A—H4B | 109.00 |
C3A—C4A—C41 | 110.6 (2) | C3A—C4A—H4B | 110.00 |
C3B—C4B—C41 | 110.6 (2) | H4A—C4A—H4B | 108.00 |
C6—C5—C42 | 119.7 (2) | C41—C4B—H42 | 109.00 |
C5—C6—C7 | 120.7 (3) | C3B—C4B—H41 | 110.00 |
C6—C7—C8 | 121.5 (3) | C3B—C4B—H42 | 110.00 |
C7—C8—C8A | 117.8 (2) | H41—C4B—H42 | 108.00 |
N9—C8A—C8 | 130.6 (2) | C41—C4B—H41 | 110.00 |
N9—C8A—C42 | 107.85 (18) | C6—C5—H5 | 120.00 |
C8—C8A—C42 | 121.6 (2) | C42—C5—H5 | 120.00 |
N9—C9A—C1 | 125.8 (2) | C7—C6—H6 | 120.00 |
N9—C9A—C41 | 109.53 (18) | C5—C6—H6 | 120.00 |
C1—C9A—C41 | 124.7 (2) | C8—C7—H7 | 119.00 |
O2A—C13—O3A | 121.7 (2) | C6—C7—H7 | 119.00 |
O2A—C13—C2A | 121.2 (2) | C8A—C8—H8 | 121.00 |
O3A—C13—C2A | 117.2 (2) | C7—C8—H8 | 121.00 |
O2B—C13—O3B | 109.2 (9) | H14B—C14A—H14C | 109.00 |
O2B—C13—C2B | 102.2 (12) | H14A—C14A—H14C | 110.00 |
O3B—C13—C2B | 148.4 (10) | O3A—C14A—H14A | 109.00 |
C4A—C41—C42 | 130.4 (2) | O3A—C14A—H14B | 109.00 |
C9A—C41—C42 | 107.00 (19) | O3A—C14A—H14C | 109.00 |
C4B—C41—C9A | 122.59 (19) | H14A—C14A—H14B | 109.00 |
C4B—C41—C42 | 130.4 (2) | O3B—C14B—H14D | 109.00 |
C4A—C41—C9A | 122.59 (19) | O3B—C14B—H14E | 109.00 |
C5—C42—C41 | 134.6 (2) | O3B—C14B—H14F | 109.00 |
C8A—C42—C41 | 106.70 (19) | H14D—C14B—H14E | 110.00 |
C5—C42—C8A | 118.7 (2) | H14D—C14B—H14F | 109.00 |
C1—C2A—H2A | 107.00 | H14E—C14B—H14F | 109.00 |
C14A—O3A—C13—C2A | 179.7 (2) | C3A—C4A—C41—C9A | −19.1 (3) |
C14A—O3A—C13—O2A | −0.1 (3) | C3A—C4A—C41—C42 | 159.3 (3) |
C8A—N9—C9A—C1 | 177.0 (2) | C6—C5—C42—C41 | −179.6 (3) |
C8A—N9—C9A—C41 | −0.7 (3) | C6—C5—C42—C8A | −1.3 (4) |
C9A—N9—C8A—C8 | −179.4 (2) | C42—C5—C6—C7 | 0.6 (4) |
C9A—N9—C8A—C42 | 0.3 (2) | C5—C6—C7—C8 | 0.2 (4) |
O1—C1—C9A—N9 | −0.4 (4) | C6—C7—C8—C8A | −0.3 (4) |
C2A—C1—C9A—C41 | −8.4 (3) | C7—C8—C8A—C42 | −0.4 (4) |
O1—C1—C2A—C13 | −24.7 (3) | C7—C8—C8A—N9 | 179.1 (2) |
C9A—C1—C2A—C3A | 32.3 (3) | N9—C8A—C42—C5 | −178.5 (2) |
C9A—C1—C2A—C13 | 160.4 (2) | N9—C8A—C42—C41 | 0.3 (3) |
O1—C1—C9A—C41 | 177.0 (2) | C8—C8A—C42—C41 | 179.9 (2) |
C2A—C1—C9A—N9 | 174.2 (2) | C8—C8A—C42—C5 | 1.2 (4) |
O1—C1—C2A—C3A | −152.8 (2) | N9—C9A—C41—C4A | 179.6 (2) |
C1—C2A—C13—O3A | 105.7 (3) | C1—C9A—C41—C42 | −176.9 (2) |
C3A—C2A—C13—O2A | 53.0 (4) | N9—C9A—C41—C42 | 0.9 (3) |
C3A—C2A—C13—O3A | −126.9 (3) | C1—C9A—C41—C4A | 1.9 (4) |
C13—C2A—C3A—C4A | −177.9 (2) | C4A—C41—C42—C5 | −0.9 (5) |
C1—C2A—C13—O2A | −74.4 (3) | C4A—C41—C42—C8A | −179.3 (2) |
C1—C2A—C3A—C4A | −52.1 (3) | C9A—C41—C42—C5 | 177.8 (3) |
C2A—C3A—C4A—C41 | 44.1 (3) | C9A—C41—C42—C8A | −0.7 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1; (vi) −x, −y+2, −z+1; (vii) −x, −y+1, −z; (viii) x−1, y, z; (ix) x, y, z−1; (x) −x−1, −y+2, −z; (xi) −x, −y+2, −z; (xii) x−1, y, z−1; (xiii) x+1, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O1ii | 0.87 | 2.07 | 2.883 (2) | 155 |
C14A—H14B···O2Aiv | 0.97 | 2.39 | 3.337 (3) | 166 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H13NO3 |
Mr | 243.25 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 203 |
a, b, c (Å) | 6.9814 (12), 8.1303 (13), 10.780 (2) |
α, β, γ (°) | 88.575 (14), 76.881 (15), 79.367 (14) |
V (Å3) | 585.59 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.36 × 0.31 × 0.22 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.890, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6572, 3176, 1673 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.717 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.221, 1.11 |
No. of reflections | 3176 |
No. of parameters | 176 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.80, −0.44 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O1i | 0.87 | 2.07 | 2.883 (2) | 155 |
C14A—H14B···O2Aii | 0.97 | 2.39 | 3.337 (3) | 166 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
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The title compound, has been analysed as part of our crystallographic studies on substituted carbazoles (Gunaseelan et al. (2007a, b); Thiruvalluvar et al. (2007)).
The molecular structure of the title compound, with the atomic numbering scheme, is shown in Fig. 1. The dihedral angle between the benzene ring and the fused pyrrole ring is 1.0 (1)°. The cyclohexene ring adopts a twist conformation. The crystal structure is stabilized by intermolecular N9—H9···O1(-x + 1,-y + 1,-z) and C14A—H14B···O2A(-x + 1,-y + 1,-z + 1) hydrogen bonds (Fig. 2).