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ISSN: 2056-9890

4,8-Di­methyl­pyrano[2,3-a]carbazol-2(11H)-one

aDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net

(Received 15 March 2009; accepted 17 March 2009; online 25 March 2009)

The mol­ecule of the title compound, C17H13NO2, is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Inter­molecular N—H⋯O and C—H⋯O hydrogen bonds are found in the crystal structure. C—H⋯π inter­actions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.

Related literature

For the synthesis of 2-methyl- and 2-phenyl-pyrano[2,3-a]carbazol-4-ones and their derivatives, see: Kavitha & Rajendra Prasad (2003[Kavitha, C. & Rajendra Prasad, K. J. (2003). J. Chem. Res. (M), pp. 1025-1036.]). For related crystal structures, see: Sridharan et al. (2007[Sridharan, M., Prasad, K. J. R. & Zeller, M. (2007). Acta Cryst. E63, o4344.]); Sridharan et al. (2008a[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008a). Acta Cryst. E64, o2155.],b[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o2157.]); Sridharan et al. (2008[Sridharan, M., Prasad, K. J. R. & Zeller, M. (2008). Acta Cryst. E64, o2156.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13NO2

  • Mr = 263.28

  • Monoclinic, C 2/c

  • a = 26.8502 (4) Å

  • b = 6.8202 (1) Å

  • c = 15.8265 (3) Å

  • β = 115.531 (2)°

  • V = 2615.21 (9) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.71 mm−1

  • T = 295 K

  • 0.48 × 0.45 × 0.18 mm

Data collection
  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.313, Tmax = 1.000 (expected range = 0.276–0.880)

  • 6122 measured reflections

  • 2703 independent reflections

  • 2218 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.132

  • S = 1.07

  • 2703 reflections

  • 186 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N11—H11⋯O2i 0.86 (2) 2.01 (2) 2.814 (2) 154.5 (19)
C14—H14B⋯O2ii 0.96 2.39 3.338 (2) 168
C6—H6⋯Cg1iii 0.93 2.90 3.389 (1) 114
C5—H5⋯Cg2iii 0.93 2.98 3.626 (1) 128
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]; (ii) x, y-1, z; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1 is the centroid of the pyrrole ring and Cg2 is the centroid of the C6B–C10A ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The title compound has been analysed as part of our crystallographic studies on pyranocarbazolones. Sridharan et al. (2007, 2008a, 2008b), also Sridharan et al. (2008) have reported the X-ray crystal sructures of related pyranocarbazolone compounds. Recently we reported (Kavitha & Rajendra Prasad, 2003) the synthesis of 2-methyl- and 2-phenyl- pyrano[2,3-a]carbazol-4-ones and their substituted derivatives.

The molecule of the title compound, C17H13NO2, (Fig.1) is nearly planar; the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms is 0.089 Å. N11—H11···O2(1/2 - x, 5/2 - y, -z) and C14—H14B···O2(x, -1 + y, z) intermolecular hydrogen bonds are found in the crystal structure. Furthermore, a C6—H6···π(1/2 - x, -1/2 + y, 1/2 - z) interaction involving the pyrrole ring (C6A,C6B,C10A,N11,C11A) and a C5—H5···π (1/2 - x, -1/2 + y, 1/2 - z) interaction involving the fused benzene ring (C6B–C10A) are also found.

Related literature top

For the synthesis of 2-methyl- and 2-phenyl-pyrano[2,3-a]carbazol-4-ones and their derivatives, see: Kavitha & Rajendra Prasad (2003). For related crystal structures, see: Sridharan et al. (2007); Sridharan et al. (2008a,b); Sridharan et al. (2008). Cg1 is the centroid of the pyrrole ring and Cg2 is the centroid of the C6B–C10A ring.

Experimental top

A mixture of 6-methyl-1-hydroxycarbazole (0.199 g, 0.001 mol) and ethyl acetoacetate (0.001 mol) was treated with fused ZnCl2/POCl3 (1.5 g / 6 ml) and heated to 373 K for 4 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was poured on to crushed ice; the solid that separated was filtered off, dried and recrystallized from ethanol to obtain the title compound as the sole product in high yield (0.267 g, 82%).

Refinement top

H11, attached to N11, was located in a difference Fourier map and refined isotropically; the final N—H distance was 0.86 (2) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 and 0.96 Å for Csp2 and methyl H atoms, respectively. Uiso(H) = xUeq(C), where x = 1.5 for methyl H atoms and 1.2 for other C-bound H atoms. The H atoms of the C18 methyl group were refined as disordered equally over two positions.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. Only one set of disordered H atoms is shown.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
4,8-Dimethylpyrano[2,3-a]carbazol-2(11H)-one top
Crystal data top
C17H13NO2F(000) = 1104
Mr = 263.28Dx = 1.337 Mg m3
Monoclinic, C2/cMelting point: 506(1) K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54184 Å
a = 26.8502 (4) ÅCell parameters from 3727 reflections
b = 6.8202 (1) Åθ = 5.7–77.3°
c = 15.8265 (3) ŵ = 0.71 mm1
β = 115.531 (2)°T = 295 K
V = 2615.21 (9) Å3Plate, colourless
Z = 80.48 × 0.45 × 0.18 mm
Data collection top
Oxford Diffraction Gemini R
diffractometer
2703 independent reflections
Radiation source: fine-focus sealed tube2218 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 10.5081 pixels mm-1θmax = 77.8°, θmin = 5.7°
ϕ and ω scansh = 3334
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
k = 86
Tmin = 0.313, Tmax = 1.000l = 1918
6122 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0834P)2 + 0.3277P]
where P = (Fo2 + 2Fc2)/3
2703 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C17H13NO2V = 2615.21 (9) Å3
Mr = 263.28Z = 8
Monoclinic, C2/cCu Kα radiation
a = 26.8502 (4) ŵ = 0.71 mm1
b = 6.8202 (1) ÅT = 295 K
c = 15.8265 (3) Å0.48 × 0.45 × 0.18 mm
β = 115.531 (2)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
2703 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)
2218 reflections with I > 2σ(I)
Tmin = 0.313, Tmax = 1.000Rint = 0.018
6122 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.22 e Å3
2703 reflectionsΔρmin = 0.18 e Å3
186 parameters
Special details top

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 > 2σ(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*/UeqOcc. (<1)
O10.29530 (4)1.01921 (13)0.07257 (7)0.0519 (3)
O20.35050 (5)1.19047 (16)0.03063 (9)0.0686 (4)
N110.19050 (5)0.97178 (18)0.07986 (8)0.0519 (3)
C20.34394 (6)1.0397 (2)0.06525 (10)0.0537 (4)
C30.38333 (6)0.8836 (2)0.10052 (10)0.0556 (4)
C40.37356 (5)0.7174 (2)0.13688 (9)0.0514 (4)
C4A0.32087 (5)0.69352 (19)0.13969 (9)0.0481 (4)
C50.30472 (6)0.5221 (2)0.17213 (9)0.0543 (4)
C60.25386 (6)0.5074 (2)0.17191 (9)0.0545 (4)
C6A0.21696 (5)0.6649 (2)0.13986 (9)0.0487 (4)
C6B0.16178 (6)0.7006 (2)0.12955 (9)0.0516 (4)
C70.12374 (6)0.5877 (3)0.14701 (10)0.0605 (5)
C80.07214 (6)0.6638 (3)0.12677 (11)0.0691 (5)
C90.05908 (6)0.8535 (3)0.09007 (11)0.0696 (6)
C100.09551 (6)0.9699 (3)0.07195 (11)0.0620 (5)
C10A0.14709 (5)0.8902 (2)0.09203 (9)0.0517 (4)
C11A0.23240 (5)0.83643 (18)0.10748 (9)0.0469 (4)
C11B0.28383 (5)0.84912 (18)0.10697 (8)0.0462 (4)
C140.41674 (6)0.5602 (3)0.17296 (12)0.0658 (5)
C180.02959 (8)0.5430 (4)0.14272 (16)0.0991 (9)
H30.417170.897750.098210.0667*
H50.329220.417560.194010.0651*
H60.243860.393320.192940.0653*
H70.133100.462340.172050.0726*
H90.024340.903510.077300.0835*
H100.085981.095600.047480.0744*
H110.1888 (7)1.081 (3)0.0516 (13)0.070 (5)*
H14A0.449160.602400.166910.0988*
H14B0.402810.442340.137390.0988*
H14C0.425900.535280.237690.0988*
H18A0.003620.618180.125050.1487*0.500
H18B0.043770.508290.207720.1487*0.500
H18C0.021680.425920.105500.1487*0.500
H18D0.044840.416740.167130.1487*0.500
H18E0.002550.526630.084460.1487*0.500
H18F0.019540.609010.186680.1487*0.500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0547 (5)0.0430 (5)0.0602 (5)0.0053 (4)0.0269 (4)0.0030 (4)
O20.0681 (6)0.0510 (6)0.0928 (8)0.0093 (4)0.0404 (6)0.0104 (5)
N110.0551 (6)0.0481 (6)0.0560 (6)0.0014 (5)0.0272 (5)0.0044 (5)
C20.0561 (7)0.0484 (7)0.0580 (8)0.0117 (6)0.0259 (6)0.0030 (6)
C30.0475 (6)0.0582 (8)0.0595 (8)0.0086 (6)0.0216 (6)0.0022 (6)
C40.0502 (7)0.0539 (7)0.0453 (6)0.0042 (5)0.0160 (5)0.0018 (5)
C4A0.0526 (7)0.0481 (7)0.0410 (6)0.0042 (5)0.0178 (5)0.0003 (5)
C50.0599 (8)0.0501 (7)0.0503 (7)0.0015 (6)0.0214 (6)0.0090 (5)
C60.0647 (8)0.0506 (7)0.0483 (7)0.0050 (6)0.0246 (6)0.0095 (5)
C6A0.0554 (7)0.0514 (7)0.0405 (6)0.0081 (5)0.0218 (5)0.0006 (5)
C6B0.0551 (7)0.0593 (8)0.0413 (6)0.0089 (6)0.0216 (5)0.0007 (5)
C70.0614 (8)0.0707 (9)0.0519 (7)0.0122 (7)0.0268 (6)0.0055 (7)
C80.0588 (8)0.0958 (12)0.0556 (8)0.0151 (8)0.0273 (7)0.0064 (8)
C90.0526 (7)0.0983 (13)0.0605 (9)0.0001 (8)0.0268 (7)0.0068 (8)
C100.0580 (8)0.0713 (9)0.0593 (8)0.0015 (7)0.0277 (6)0.0046 (7)
C10A0.0545 (7)0.0574 (7)0.0459 (6)0.0063 (6)0.0241 (5)0.0014 (5)
C11A0.0536 (7)0.0455 (6)0.0419 (6)0.0041 (5)0.0208 (5)0.0009 (5)
C11B0.0537 (7)0.0436 (6)0.0413 (6)0.0071 (5)0.0205 (5)0.0009 (4)
C140.0527 (7)0.0678 (9)0.0709 (9)0.0052 (7)0.0210 (7)0.0094 (7)
C180.0691 (10)0.137 (2)0.0963 (14)0.0196 (12)0.0406 (10)0.0270 (14)
Geometric parameters (Å, º) top
O1—C21.367 (2)C8—C181.515 (3)
O1—C11B1.3717 (16)C9—C101.382 (3)
O2—C21.2132 (18)C10—C10A1.391 (2)
N11—C10A1.378 (2)C11A—C11B1.387 (2)
N11—C11A1.3730 (19)C3—H30.9300
N11—H110.86 (2)C5—H50.9300
C2—C31.433 (2)C6—H60.9300
C3—C41.347 (2)C7—H70.9300
C4—C4A1.444 (2)C9—H90.9300
C4—C141.500 (2)C10—H100.9300
C4A—C11B1.3927 (19)C14—H14A0.9600
C4A—C51.418 (2)C14—H14B0.9600
C5—C61.368 (2)C14—H14C0.9600
C6—C6A1.400 (2)C18—H18A0.9600
C6A—C11A1.4093 (19)C18—H18B0.9600
C6A—C6B1.440 (2)C18—H18C0.9600
C6B—C71.399 (2)C18—H18D0.9600
C6B—C10A1.4066 (19)C18—H18E0.9600
C7—C81.382 (3)C18—H18F0.9600
C8—C91.400 (3)
O1···N112.8837 (19)C5···H14C2.9600
O2···N11i2.8136 (17)C5···H14B2.9600
O2···C14ii3.338 (2)C6A···H6v2.8500
O1···H112.77 (2)C6B···H5v3.0800
O2···H14Bii2.3900C9···H14Cv2.8600
O2···H10i2.9000C11A···H6v2.9700
O2···H11i2.01 (2)C14···H52.6900
N11···O12.8837 (19)C18···H3vii2.9600
N11···O2i2.8136 (17)H3···H14A2.2700
N11···C4iii3.3621 (17)H3···C18viii2.9600
C2···C6iii3.548 (2)H3···H18Aviii2.4900
C2···C6Aiii3.2532 (19)H3···H18Eviii2.4200
C2···C6Biii3.436 (2)H5···C142.6900
C3···C10Aiii3.3608 (19)H5···H14B2.5000
C3···C6Biii3.3546 (19)H5···H14C2.5100
C4···N11iii3.3621 (17)H5···C6Biv3.0800
C4···C10Aiii3.4985 (18)H6···C6Aiv2.8500
C4A···C11Aiii3.5450 (18)H6···C11Aiv2.9700
C5···C10Aiv3.5003 (18)H7···H18D2.3600
C6···C6Aiv3.5963 (19)H9···H18A2.3300
C6···C11Aiv3.5463 (19)H9···H9ix2.5800
C6···C2iii3.548 (2)H10···O2i2.9000
C6A···C6v3.5963 (19)H11···O12.77 (2)
C6A···C2iii3.2532 (19)H11···O2i2.01 (2)
C6B···C2iii3.436 (2)H11···C2i3.08 (2)
C6B···C3iii3.3546 (19)H14A···H32.2700
C10A···C4iii3.4985 (18)H14B···O2vi2.3900
C10A···C3iii3.3608 (19)H14B···C52.9600
C10A···C5v3.5003 (18)H14B···H52.5000
C11A···C6v3.5463 (19)H14C···C52.9600
C11A···C11Biii3.4692 (18)H14C···H52.5100
C11A···C4Aiii3.5450 (18)H14C···C9iv2.8600
C11B···C11Biii3.3601 (16)H18A···H92.3300
C11B···C11Aiii3.4692 (18)H18A···H3vii2.4900
C14···O2vi3.338 (2)H18B···C3iv2.9400
C2···H11i3.08 (2)H18D···H72.3600
C3···H18Bv2.9400H18E···H3vii2.4200
C2—O1—C11B120.41 (11)C4—C3—H3119.00
C10A—N11—C11A108.09 (12)C4A—C5—H5119.00
C11A—N11—H11126.9 (14)C6—C5—H5119.00
C10A—N11—H11124.3 (14)C5—C6—H6120.00
O1—C2—C3117.55 (13)C6A—C6—H6120.00
O1—C2—O2117.06 (14)C6B—C7—H7120.00
O2—C2—C3125.38 (17)C8—C7—H7120.00
C2—C3—C4122.99 (16)C8—C9—H9119.00
C4A—C4—C14120.98 (13)C10—C9—H9119.00
C3—C4—C14120.22 (15)C9—C10—H10122.00
C3—C4—C4A118.81 (13)C10A—C10—H10122.00
C4—C4A—C5124.12 (13)C4—C14—H14A109.00
C4—C4A—C11B117.05 (12)C4—C14—H14B109.00
C5—C4A—C11B118.82 (14)C4—C14—H14C109.00
C4A—C5—C6121.36 (13)H14A—C14—H14B109.00
C5—C6—C6A119.64 (13)H14A—C14—H14C109.00
C6—C6A—C11A119.71 (14)H14B—C14—H14C109.00
C6B—C6A—C11A105.55 (12)C8—C18—H18A109.00
C6—C6A—C6B134.74 (13)C8—C18—H18B109.00
C7—C6B—C10A119.59 (15)C8—C18—H18C109.00
C6A—C6B—C7133.48 (14)C8—C18—H18D109.00
C6A—C6B—C10A106.92 (13)C8—C18—H18E109.00
C6B—C7—C8119.48 (17)C8—C18—H18F109.00
C9—C8—C18119.98 (17)H18A—C18—H18B109.00
C7—C8—C18120.65 (19)H18A—C18—H18C109.00
C7—C8—C9119.36 (17)H18A—C18—H18D141.00
C8—C9—C10122.95 (17)H18A—C18—H18E56.00
C9—C10—C10A116.87 (17)H18A—C18—H18F56.00
N11—C10A—C10128.99 (14)H18B—C18—H18C109.00
N11—C10A—C6B109.27 (13)H18B—C18—H18D56.00
C6B—C10A—C10121.74 (15)H18B—C18—H18E141.00
N11—C11A—C11B129.60 (12)H18B—C18—H18F56.00
C6A—C11A—C11B120.23 (12)H18C—C18—H18D56.00
N11—C11A—C6A110.17 (13)H18C—C18—H18E56.00
C4A—C11B—C11A120.23 (12)H18C—C18—H18F141.00
O1—C11B—C4A123.06 (13)H18D—C18—H18E109.00
O1—C11B—C11A116.71 (12)H18D—C18—H18F109.00
C2—C3—H3118.00H18E—C18—H18F109.00
C11B—O1—C2—O2176.99 (12)C6—C6A—C6B—C71.0 (3)
C11B—O1—C2—C34.14 (18)C6—C6A—C6B—C10A179.50 (15)
C2—O1—C11B—C4A2.84 (18)C11A—C6A—C6B—C7178.38 (15)
C2—O1—C11B—C11A176.72 (12)C11A—C6A—C6B—C10A0.12 (14)
C11A—N11—C10A—C6B0.99 (15)C6—C6A—C11A—N11179.77 (12)
C11A—N11—C10A—C10178.52 (14)C6—C6A—C11A—C11B0.25 (19)
C10A—N11—C11A—C6A1.08 (15)C6B—C6A—C11A—N110.74 (15)
C10A—N11—C11A—C11B178.89 (13)C6B—C6A—C11A—C11B179.24 (12)
O1—C2—C3—C42.4 (2)C6A—C6B—C7—C8178.08 (15)
O2—C2—C3—C4178.81 (15)C10A—C6B—C7—C80.3 (2)
C2—C3—C4—C4A0.7 (2)C6A—C6B—C10A—N110.53 (15)
C2—C3—C4—C14179.72 (14)C6A—C6B—C10A—C10179.03 (13)
C3—C4—C4A—C5176.95 (13)C7—C6B—C10A—N11179.27 (12)
C3—C4—C4A—C11B2.11 (19)C7—C6B—C10A—C100.3 (2)
C14—C4—C4A—C52.6 (2)C6B—C7—C8—C90.7 (2)
C14—C4—C4A—C11B178.34 (13)C6B—C7—C8—C18178.49 (16)
C4—C4A—C5—C6179.13 (13)C7—C8—C9—C100.6 (3)
C11B—C4A—C5—C60.09 (19)C18—C8—C9—C10178.59 (17)
C4—C4A—C11B—O10.40 (18)C8—C9—C10—C10A0.1 (2)
C4—C4A—C11B—C11A179.94 (13)C9—C10—C10A—N11179.08 (14)
C5—C4A—C11B—O1178.72 (11)C9—C10—C10A—C6B0.4 (2)
C5—C4A—C11B—C11A0.83 (18)N11—C11A—C11B—O11.3 (2)
C4A—C5—C6—C6A0.6 (2)N11—C11A—C11B—C4A179.12 (13)
C5—C6—C6A—C6B179.79 (14)C6A—C11A—C11B—O1178.66 (11)
C5—C6—C6A—C11A0.48 (19)C6A—C11A—C11B—C4A0.91 (19)
Symmetry codes: (i) x+1/2, y+5/2, z; (ii) x, y+1, z; (iii) x+1/2, y+3/2, z; (iv) x+1/2, y1/2, z+1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x, y1, z; (vii) x1/2, y1/2, z; (viii) x+1/2, y+1/2, z; (ix) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O2i0.86 (2)2.01 (2)2.814 (2)154.5 (19)
C14—H14B···O2vi0.962.393.338 (2)168
C6—H6···Cg1iv0.932.903.389 (1)114
C5—H5···Cg2iv0.932.983.626 (1)128
Symmetry codes: (i) x+1/2, y+5/2, z; (iv) x+1/2, y1/2, z+1/2; (vi) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H13NO2
Mr263.28
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)26.8502 (4), 6.8202 (1), 15.8265 (3)
β (°) 115.531 (2)
V3)2615.21 (9)
Z8
Radiation typeCu Kα
µ (mm1)0.71
Crystal size (mm)0.48 × 0.45 × 0.18
Data collection
DiffractometerOxford Diffraction Gemini R
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2008)
Tmin, Tmax0.313, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6122, 2703, 2218
Rint0.018
(sin θ/λ)max1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.132, 1.07
No. of reflections2703
No. of parameters186
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.18

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O2i0.86 (2)2.01 (2)2.814 (2)154.5 (19)
C14—H14B···O2ii0.962.393.338 (2)168
C6—H6···Cg1iii0.932.903.389 (1)114
C5—H5···Cg2iii0.932.983.626 (1)128
Symmetry codes: (i) x+1/2, y+5/2, z; (ii) x, y1, z; (iii) x+1/2, y1/2, z+1/2.
 

Acknowledgements

We acknowledge the UGC, New Delhi, India, for the award of Major Research Project grant No. F.No.31–122/2005. MS thanks the UGC, New Delhi, India, for the award of a research fellowship. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationKavitha, C. & Rajendra Prasad, K. J. (2003). J. Chem. Res. (M), pp. 1025-1036.
First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008a). Acta Cryst. E64, o2155.  Web of Science CSD CrossRef IUCr Journals
First citationSridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o2157.  Web of Science CSD CrossRef IUCr Journals
First citationSridharan, M., Prasad, K. J. R. & Zeller, M. (2007). Acta Cryst. E63, o4344.  Web of Science CSD CrossRef IUCr Journals
First citationSridharan, M., Prasad, K. J. R. & Zeller, M. (2008). Acta Cryst. E64, o2156.  Web of Science CSD CrossRef IUCr Journals

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