Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702644X/bq2018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702644X/bq2018Isup2.hkl |
CCDC reference: 654869
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.003 Å
- R factor = 0.067
- wR factor = 0.177
- Data-to-parameter ratio = 21.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.67 mm PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: Knolker & Reddy (2002); Gunaseelan et al. (2007a,b). Due to the interesting and important properties of carbazoles, a number of methodologies for the construction of the carbazole ring with other heterocyclic compounds have been reported (Knolker & Reddy, 2002). Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.
The mixture of 9-methyl-1,2,3,4-tetrahydrocarbazol-1-one (200 mg, 0.001 mol), dimethyl carbonate (2 ml), sodium hydride in mineral oil (300 mg), catalytic amount of potassium hydride (0.030 mg) [CAUTION: Potassium hydride is highly pyrophoric in dry condition] was refluxed on a water bath for 3 h. After cooling the mixture was carefully neutralized using glacial acetic acid and then poured into crushed ice. It was extracted with ethyl acetate and purified by column chromatography over silica gel using petroleum ether/ethyl acetate (98:2) as eluant to get the pure compound (I) (205 mg, 80%). It was recrystallized using glacial acetic acid.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 to 1.5 times Ueq(C).
The molecular structure of (I), with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 0.9 (1)°. The cyclohexene ring is in half-chair form. In the crystal structure, the molecules are stabilized by intermolecular C9—H9A···O21(x + 1, y, z) and C22—H22B···O1(-x + 1/2, y + 1/2, -z) hydrogen bonds (Fig. 2).
For related literature, see: Knolker & Reddy (2002); Gunaseelan et al. (2007a,b). Due to the interesting and important properties of carbazoles, a number of methodologies for the construction of the carbazole ring with other heterocyclic compounds have been reported (Knolker & Reddy, 2002). Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C15H15NO3 | F(000) = 544 |
Mr = 257.28 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/a | Melting point: 361(1) K |
Hall symbol: -P 2yab | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1267 (3) Å | Cell parameters from 7041 reflections |
b = 8.2114 (3) Å | θ = 4.7–30.7° |
c = 17.2304 (9) Å | µ = 0.09 mm−1 |
β = 91.151 (4)° | T = 203 K |
V = 1291.04 (9) Å3 | Plate, colourless |
Z = 4 | 0.67 × 0.35 × 0.32 mm |
Oxford Diffraction Gemini diffractometer | 2639 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.038 |
Graphite monochromator | θmax = 30.7°, θmin = 4.7° |
φ and ω scans | h = −13→12 |
13753 measured reflections | k = −11→10 |
3646 independent reflections | l = −23→23 |
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) = 0.177 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.8204P] where P = (Fo2 + 2Fc2)/3 |
3646 reflections | (Δ/σ)max < 0.001 |
174 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C15H15NO3 | V = 1291.04 (9) Å3 |
Mr = 257.28 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 9.1267 (3) Å | µ = 0.09 mm−1 |
b = 8.2114 (3) Å | T = 203 K |
c = 17.2304 (9) Å | 0.67 × 0.35 × 0.32 mm |
β = 91.151 (4)° |
Oxford Diffraction Gemini diffractometer | 2639 reflections with I > 2σ(I) |
13753 measured reflections | Rint = 0.038 |
3646 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.35 e Å−3 |
3646 reflections | Δρmin = −0.18 e Å−3 |
174 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 | ||
O1 | 0.41622 (18) | 0.4836 (2) | 0.11376 (10) | 0.0517 (5) | |
O21 | 0.06438 (19) | 0.5261 (2) | 0.15535 (11) | 0.0624 (7) | |
O22 | 0.17217 (18) | 0.7308 (2) | 0.09356 (9) | 0.0506 (5) | |
N9 | 0.66243 (17) | 0.4350 (2) | 0.22709 (11) | 0.0383 (5) | |
C1 | 0.4145 (2) | 0.5367 (2) | 0.17927 (12) | 0.0360 (6) | |
C2 | 0.2865 (2) | 0.6423 (2) | 0.20840 (12) | 0.0375 (6) | |
C3 | 0.2474 (2) | 0.5956 (3) | 0.29114 (13) | 0.0439 (6) | |
C4 | 0.3767 (2) | 0.6254 (3) | 0.34675 (12) | 0.0444 (7) | |
C4A | 0.5123 (2) | 0.5489 (2) | 0.31546 (12) | 0.0359 (6) | |
C4B | 0.6424 (2) | 0.4969 (2) | 0.35477 (12) | 0.0380 (6) | |
C5 | 0.6906 (3) | 0.5009 (3) | 0.43246 (14) | 0.0485 (7) | |
C6 | 0.8261 (3) | 0.4360 (3) | 0.45130 (16) | 0.0572 (8) | |
C7 | 0.9150 (3) | 0.3685 (3) | 0.39403 (17) | 0.0557 (9) | |
C8 | 0.8729 (2) | 0.3644 (3) | 0.31774 (16) | 0.0486 (8) | |
C8A | 0.7334 (2) | 0.4271 (2) | 0.29785 (13) | 0.0383 (6) | |
C9 | 0.7206 (2) | 0.3755 (3) | 0.15384 (14) | 0.0473 (7) | |
C9A | 0.5280 (2) | 0.5097 (2) | 0.23855 (12) | 0.0348 (6) | |
C21 | 0.1608 (2) | 0.6243 (3) | 0.15081 (13) | 0.0418 (6) | |
C22 | 0.0692 (3) | 0.7132 (4) | 0.02922 (15) | 0.0645 (10) | |
H2 | 0.31830 | 0.75754 | 0.20847 | 0.0450* | |
H3A | 0.16314 | 0.66014 | 0.30756 | 0.0526* | |
H3B | 0.21973 | 0.48036 | 0.29273 | 0.0526* | |
H4A | 0.39199 | 0.74274 | 0.35328 | 0.0533* | |
H4B | 0.35560 | 0.57871 | 0.39767 | 0.0533* | |
H5 | 0.63187 | 0.54680 | 0.47094 | 0.0583* | |
H6 | 0.85943 | 0.43700 | 0.50328 | 0.0686* | |
H7 | 1.00655 | 0.32471 | 0.40881 | 0.0669* | |
H8 | 0.93460 | 0.32131 | 0.27981 | 0.0584* | |
H9A | 0.82570 | 0.36047 | 0.15935 | 0.0709* | |
H9B | 0.69992 | 0.45422 | 0.11309 | 0.0709* | |
H9C | 0.67470 | 0.27242 | 0.14052 | 0.0709* | |
H22A | 0.08888 | 0.61257 | 0.00187 | 0.0968* | |
H22B | 0.07942 | 0.80450 | −0.00599 | 0.0968* | |
H22C | −0.02982 | 0.71084 | 0.04863 | 0.0968* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0440 (9) | 0.0605 (10) | 0.0508 (9) | −0.0004 (7) | 0.0052 (7) | −0.0159 (8) |
O21 | 0.0402 (9) | 0.0697 (12) | 0.0770 (13) | −0.0125 (8) | −0.0038 (8) | 0.0176 (10) |
O22 | 0.0592 (10) | 0.0453 (9) | 0.0472 (9) | −0.0008 (8) | −0.0009 (7) | 0.0056 (7) |
N9 | 0.0304 (8) | 0.0309 (8) | 0.0540 (11) | 0.0005 (6) | 0.0114 (7) | −0.0041 (7) |
C1 | 0.0320 (9) | 0.0334 (9) | 0.0430 (11) | −0.0033 (7) | 0.0087 (8) | −0.0001 (8) |
C2 | 0.0336 (9) | 0.0316 (9) | 0.0475 (11) | 0.0045 (7) | 0.0060 (8) | 0.0026 (8) |
C3 | 0.0311 (9) | 0.0505 (12) | 0.0504 (12) | 0.0118 (9) | 0.0100 (8) | 0.0041 (10) |
C4 | 0.0383 (10) | 0.0569 (13) | 0.0383 (11) | 0.0125 (9) | 0.0099 (8) | 0.0017 (9) |
C4A | 0.0315 (9) | 0.0316 (9) | 0.0450 (11) | 0.0014 (7) | 0.0090 (8) | 0.0040 (8) |
C4B | 0.0308 (9) | 0.0325 (9) | 0.0509 (12) | 0.0006 (7) | 0.0077 (8) | 0.0079 (8) |
C5 | 0.0401 (11) | 0.0558 (14) | 0.0499 (13) | 0.0037 (10) | 0.0061 (9) | 0.0109 (10) |
C6 | 0.0436 (12) | 0.0669 (16) | 0.0609 (15) | 0.0017 (12) | −0.0019 (11) | 0.0159 (12) |
C7 | 0.0348 (11) | 0.0501 (14) | 0.0822 (19) | 0.0085 (10) | −0.0021 (11) | 0.0109 (12) |
C8 | 0.0333 (10) | 0.0353 (11) | 0.0776 (17) | 0.0060 (8) | 0.0088 (10) | 0.0010 (10) |
C8A | 0.0303 (9) | 0.0266 (9) | 0.0583 (13) | 0.0002 (7) | 0.0077 (8) | 0.0036 (8) |
C9 | 0.0374 (10) | 0.0412 (11) | 0.0638 (14) | 0.0042 (9) | 0.0158 (10) | −0.0125 (10) |
C9A | 0.0295 (9) | 0.0277 (9) | 0.0476 (11) | −0.0009 (7) | 0.0100 (7) | 0.0004 (8) |
C21 | 0.0381 (10) | 0.0401 (11) | 0.0474 (12) | 0.0054 (8) | 0.0073 (9) | 0.0016 (9) |
C22 | 0.0790 (19) | 0.0707 (18) | 0.0437 (14) | 0.0033 (15) | −0.0046 (12) | 0.0015 (12) |
O1—C1 | 1.210 (3) | C6—C7 | 1.404 (4) |
O21—C21 | 1.197 (3) | C7—C8 | 1.363 (4) |
O22—C21 | 1.324 (3) | C8—C8A | 1.409 (3) |
O22—C22 | 1.446 (3) | C2—H2 | 0.9900 |
N9—C8A | 1.371 (3) | C3—H3A | 0.9800 |
N9—C9 | 1.463 (3) | C3—H3B | 0.9800 |
N9—C9A | 1.389 (2) | C4—H4A | 0.9800 |
C1—C2 | 1.547 (3) | C4—H4B | 0.9800 |
C1—C9A | 1.457 (3) | C5—H5 | 0.9400 |
C2—C3 | 1.526 (3) | C6—H6 | 0.9400 |
C2—C21 | 1.509 (3) | C7—H7 | 0.9400 |
C3—C4 | 1.525 (3) | C8—H8 | 0.9400 |
C4—C4A | 1.498 (3) | C9—H9A | 0.9700 |
C4A—C4B | 1.421 (3) | C9—H9B | 0.9700 |
C4A—C9A | 1.374 (3) | C9—H9C | 0.9700 |
C4B—C5 | 1.401 (3) | C22—H22A | 0.9700 |
C4B—C8A | 1.419 (3) | C22—H22B | 0.9700 |
C5—C6 | 1.379 (4) | C22—H22C | 0.9700 |
O1···O22 | 3.028 (2) | C9···H8 | 2.9200 |
O1···N9 | 2.974 (2) | C9A···H8v | 2.9400 |
O1···C9 | 2.984 (3) | C9A···H3B | 2.9900 |
O1···C22i | 3.217 (3) | C22···H22Aix | 3.0800 |
O1···C22ii | 3.321 (3) | H2···C4A | 3.0600 |
O21···C9iii | 3.372 (3) | H2···H4A | 2.5700 |
O22···C1iv | 3.391 (2) | H2···N9iv | 2.9200 |
O22···O1 | 3.028 (2) | H3A···C4Aiv | 2.7600 |
O1···H22Bii | 2.3700 | H3A···C4Biv | 2.9400 |
O1···H9B | 2.6000 | H3B···O21 | 2.7600 |
O1···H22Ci | 2.8000 | H3B···C9A | 2.9900 |
O21···H9Aiii | 2.5700 | H4A···H2 | 2.5700 |
O21···H3B | 2.7600 | H4B···C5viii | 3.0400 |
O21···H9Cv | 2.6600 | H4B···H5viii | 2.4900 |
O21···H22A | 2.7500 | H5···H4Bviii | 2.4900 |
O21···H22C | 2.5200 | H7···C4Bx | 3.0700 |
O22···H9Biv | 2.6200 | H8···C9 | 2.9200 |
O22···H22Ci | 2.8800 | H8···H9A | 2.3100 |
N9···O1 | 2.974 (2) | H8···C9Ax | 2.9400 |
N9···H2i | 2.9200 | H9A···O21vi | 2.5700 |
C1···O22i | 3.391 (2) | H9A···C8 | 2.7500 |
C9···O21vi | 3.372 (3) | H9A···H8 | 2.3100 |
C9···O1 | 2.984 (3) | H9B···O1 | 2.6000 |
C9A···C21i | 3.586 (3) | H9B···C1 | 2.9400 |
C21···C9Aiv | 3.586 (3) | H9B···O22i | 2.6200 |
C22···O1iv | 3.217 (3) | H9C···O21x | 2.6600 |
C22···O1vii | 3.321 (3) | H22A···O21 | 2.7500 |
C1···H9B | 2.9400 | H22A···C22ix | 3.0800 |
C4A···H2 | 3.0600 | H22A···H22Aix | 2.4600 |
C4A···H3Ai | 2.7600 | H22B···O1vii | 2.3700 |
C4B···H3Ai | 2.9400 | H22C···O21 | 2.5200 |
C4B···H7v | 3.0700 | H22C···O1iv | 2.8000 |
C5···H4Bviii | 3.0400 | H22C···O22iv | 2.8800 |
C8···H9A | 2.7500 | ||
C21—O22—C22 | 116.47 (19) | C3—C2—H2 | 108.00 |
C8A—N9—C9 | 125.34 (16) | C21—C2—H2 | 108.00 |
C8A—N9—C9A | 107.30 (17) | C2—C3—H3A | 109.00 |
C9—N9—C9A | 127.36 (17) | C2—C3—H3B | 110.00 |
O1—C1—C2 | 121.91 (18) | C4—C3—H3A | 109.00 |
O1—C1—C9A | 125.21 (17) | C4—C3—H3B | 110.00 |
C2—C1—C9A | 112.88 (17) | H3A—C3—H3B | 108.00 |
C1—C2—C3 | 110.78 (16) | C3—C4—H4A | 110.00 |
C1—C2—C21 | 107.51 (16) | C3—C4—H4B | 110.00 |
C3—C2—C21 | 113.63 (16) | C4A—C4—H4A | 110.00 |
C2—C3—C4 | 110.75 (16) | C4A—C4—H4B | 110.00 |
C3—C4—C4A | 109.94 (17) | H4A—C4—H4B | 108.00 |
C4—C4A—C4B | 130.02 (18) | C4B—C5—H5 | 121.00 |
C4—C4A—C9A | 123.25 (17) | C6—C5—H5 | 121.00 |
C4B—C4A—C9A | 106.68 (16) | C5—C6—H6 | 119.00 |
C4A—C4B—C5 | 133.8 (2) | C7—C6—H6 | 120.00 |
C4A—C4B—C8A | 106.68 (18) | C6—C7—H7 | 119.00 |
C5—C4B—C8A | 119.54 (19) | C8—C7—H7 | 119.00 |
C4B—C5—C6 | 118.6 (2) | C7—C8—H8 | 121.00 |
C5—C6—C7 | 121.0 (2) | C8A—C8—H8 | 121.00 |
C6—C7—C8 | 122.1 (2) | N9—C9—H9A | 109.00 |
C7—C8—C8A | 117.5 (2) | N9—C9—H9B | 109.00 |
N9—C8A—C4B | 108.85 (16) | N9—C9—H9C | 109.00 |
N9—C8A—C8 | 130.0 (2) | H9A—C9—H9B | 109.00 |
C4B—C8A—C8 | 121.2 (2) | H9A—C9—H9C | 109.00 |
N9—C9A—C1 | 125.80 (18) | H9B—C9—H9C | 109.00 |
N9—C9A—C4A | 110.49 (17) | O22—C22—H22A | 110.00 |
C1—C9A—C4A | 123.64 (17) | O22—C22—H22B | 109.00 |
O21—C21—O22 | 124.2 (2) | O22—C22—H22C | 109.00 |
O21—C21—C2 | 125.0 (2) | H22A—C22—H22B | 109.00 |
O22—C21—C2 | 110.82 (17) | H22A—C22—H22C | 109.00 |
C1—C2—H2 | 108.00 | H22B—C22—H22C | 109.00 |
C22—O22—C21—C2 | 172.37 (19) | C1—C2—C3—C4 | 61.9 (2) |
C22—O22—C21—O21 | −6.8 (3) | C2—C3—C4—C4A | −50.2 (2) |
C9—N9—C8A—C8 | 0.4 (3) | C3—C4—C4A—C9A | 20.5 (3) |
C9A—N9—C8A—C4B | 0.30 (19) | C3—C4—C4A—C4B | −156.62 (19) |
C8A—N9—C9A—C1 | −177.24 (16) | C4—C4A—C4B—C5 | −1.6 (4) |
C8A—N9—C9A—C4A | −0.2 (2) | C9A—C4A—C4B—C8A | 0.19 (19) |
C9A—N9—C8A—C8 | −179.3 (2) | C4—C4A—C4B—C8A | 177.68 (19) |
C9—N9—C8A—C4B | 180.00 (17) | C9A—C4A—C4B—C5 | −179.1 (2) |
C9—N9—C9A—C4A | −179.87 (19) | C4B—C4A—C9A—N9 | 0.0 (2) |
C9—N9—C9A—C1 | 3.1 (3) | C4B—C4A—C9A—C1 | 177.13 (16) |
O1—C1—C2—C21 | 14.5 (2) | C4—C4A—C9A—N9 | −177.72 (17) |
O1—C1—C2—C3 | 139.23 (19) | C4—C4A—C9A—C1 | −0.6 (3) |
O1—C1—C9A—N9 | 7.6 (3) | C4A—C4B—C5—C6 | 179.1 (2) |
C9A—C1—C2—C3 | −40.5 (2) | C4A—C4B—C8A—C8 | 179.35 (18) |
C9A—C1—C2—C21 | −165.21 (16) | C8A—C4B—C5—C6 | −0.1 (3) |
C2—C1—C9A—C4A | 10.6 (2) | C4A—C4B—C8A—N9 | −0.30 (19) |
C2—C1—C9A—N9 | −172.67 (16) | C5—C4B—C8A—C8 | −1.3 (3) |
O1—C1—C9A—C4A | −169.09 (18) | C5—C4B—C8A—N9 | 179.10 (18) |
C21—C2—C3—C4 | −176.95 (18) | C4B—C5—C6—C7 | 0.6 (4) |
C1—C2—C21—O21 | 92.4 (2) | C5—C6—C7—C8 | 0.3 (4) |
C3—C2—C21—O21 | −30.6 (3) | C6—C7—C8—C8A | −1.7 (4) |
C3—C2—C21—O22 | 150.21 (18) | C7—C8—C8A—C4B | 2.1 (3) |
C1—C2—C21—O22 | −86.8 (2) | C7—C8—C8A—N9 | −178.3 (2) |
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) −x+1/2, y−1/2, −z; (iii) x−1, y, z; (iv) x−1/2, −y+3/2, z; (v) x−1/2, −y+1/2, z; (vi) x+1, y, z; (vii) −x+1/2, y+1/2, −z; (viii) −x+1, −y+1, −z+1; (ix) −x, −y+1, −z; (x) x+1/2, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O21vi | 0.97 | 2.57 | 3.372 (3) | 140 |
C22—H22B···O1vii | 0.97 | 2.37 | 3.321 (3) | 167 |
Symmetry codes: (vi) x+1, y, z; (vii) −x+1/2, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H15NO3 |
Mr | 257.28 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 203 |
a, b, c (Å) | 9.1267 (3), 8.2114 (3), 17.2304 (9) |
β (°) | 91.151 (4) |
V (Å3) | 1291.04 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.67 × 0.35 × 0.32 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13753, 3646, 2639 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.719 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.177, 1.14 |
No. of reflections | 3646 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.18 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O21i | 0.97 | 2.57 | 3.372 (3) | 140 |
C22—H22B···O1ii | 0.97 | 2.37 | 3.321 (3) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z. |
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The molecular structure of (I), with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 0.9 (1)°. The cyclohexene ring is in half-chair form. In the crystal structure, the molecules are stabilized by intermolecular C9—H9A···O21(x + 1, y, z) and C22—H22B···O1(-x + 1/2, y + 1/2, -z) hydrogen bonds (Fig. 2).