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

Sridharan, M.; Rajendra Prasad, K.J.; Thomas Gunaseelan, A.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536809009854

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o830

doi:10.1107/S1600536809009854

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

M. Sridharan,^a K. J. Rajendra Prasad,^a A. Thomas Gunaseelan,^b A. Thiruvalluvar ^b ^* and R. J. Butcher ^c

^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 ). For related crystal structures, see: Sridharan et al. (2007 ); Sridharan et al. (2008a ,b ); Sridharan et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₃NO₂
M_r = 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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.313, T_max = 1.000 (expected range = 0.276–0.880)
6122 measured reflections
2703 independent reflections
2218 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009854/wn2315sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009854/wn2315Isup2.hkl

checkCIF report

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%).

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

	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.
	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

C₁₇H₁₃NO₂	F(000) = 1104
M_r = 263.28	D_x = 1.337 Mg m⁻³
Monoclinic, C2/c	Melting point: 506(1) K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54184 Å
a = 26.8502 (4) Å	Cell parameters from 3727 reflections
b = 6.8202 (1) Å	θ = 5.7–77.3°
c = 15.8265 (3) Å	µ = 0.71 mm⁻¹
β = 115.531 (2)°	T = 295 K
V = 2615.21 (9) Å³	Plate, colourless
Z = 8	0.48 × 0.45 × 0.18 mm

Data collection top

Oxford Diffraction Gemini R diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2218 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.8°, θ_min = 5.7°
ϕ and ω scans	h = −33→34
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→6
T_min = 0.313, T_max = 1.000	l = −19→18
6122 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0834P)² + 0.3277P] where P = (F_o² + 2F_c²)/3
2703 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₃NO₂	V = 2615.21 (9) Å³
M_r = 263.28	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 26.8502 (4) Å	µ = 0.71 mm⁻¹
b = 6.8202 (1) Å	T = 295 K
c = 15.8265 (3) Å	0.48 × 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)
T_min = 0.313, T_max = 1.000	R_int = 0.018
6122 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.22 e Å⁻³
2703 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.29530 (4)	1.01921 (13)	0.07257 (7)	0.0519 (3)
O2	0.35050 (5)	1.19047 (16)	0.03063 (9)	0.0686 (4)
N11	0.19050 (5)	0.97178 (18)	0.07986 (8)	0.0519 (3)
C2	0.34394 (6)	1.0397 (2)	0.06525 (10)	0.0537 (4)
C3	0.38333 (6)	0.8836 (2)	0.10052 (10)	0.0556 (4)
C4	0.37356 (5)	0.7174 (2)	0.13688 (9)	0.0514 (4)
C4A	0.32087 (5)	0.69352 (19)	0.13969 (9)	0.0481 (4)
C5	0.30472 (6)	0.5221 (2)	0.17213 (9)	0.0543 (4)
C6	0.25386 (6)	0.5074 (2)	0.17191 (9)	0.0545 (4)
C6A	0.21696 (5)	0.6649 (2)	0.13986 (9)	0.0487 (4)
C6B	0.16178 (6)	0.7006 (2)	0.12955 (9)	0.0516 (4)
C7	0.12374 (6)	0.5877 (3)	0.14701 (10)	0.0605 (5)
C8	0.07214 (6)	0.6638 (3)	0.12677 (11)	0.0691 (5)
C9	0.05908 (6)	0.8535 (3)	0.09007 (11)	0.0696 (6)
C10	0.09551 (6)	0.9699 (3)	0.07195 (11)	0.0620 (5)
C10A	0.14709 (5)	0.8902 (2)	0.09203 (9)	0.0517 (4)
C11A	0.23240 (5)	0.83643 (18)	0.10748 (9)	0.0469 (4)
C11B	0.28383 (5)	0.84912 (18)	0.10697 (8)	0.0462 (4)
C14	0.41674 (6)	0.5602 (3)	0.17296 (12)	0.0658 (5)
C18	0.02959 (8)	0.5430 (4)	0.14272 (16)	0.0991 (9)
H3	0.41717	0.89775	0.09821	0.0667*
H5	0.32922	0.41756	0.19401	0.0651*
H6	0.24386	0.39332	0.19294	0.0653*
H7	0.13310	0.46234	0.17205	0.0726*
H9	0.02434	0.90351	0.07730	0.0835*
H10	0.08598	1.09560	0.04748	0.0744*
H11	0.1888 (7)	1.081 (3)	0.0516 (13)	0.070 (5)*
H14A	0.44916	0.60240	0.16691	0.0988*
H14B	0.40281	0.44234	0.13739	0.0988*
H14C	0.42590	0.53528	0.23769	0.0988*
H18A	−0.00362	0.61818	0.12505	0.1487*	0.500
H18B	0.04377	0.50829	0.20772	0.1487*	0.500
H18C	0.02168	0.42592	0.10550	0.1487*	0.500
H18D	0.04484	0.41674	0.16713	0.1487*	0.500
H18E	−0.00255	0.52663	0.08446	0.1487*	0.500
H18F	0.01954	0.60901	0.18668	0.1487*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0547 (5)	0.0430 (5)	0.0602 (5)	−0.0053 (4)	0.0269 (4)	0.0030 (4)
O2	0.0681 (6)	0.0510 (6)	0.0928 (8)	−0.0093 (4)	0.0404 (6)	0.0104 (5)
N11	0.0551 (6)	0.0481 (6)	0.0560 (6)	−0.0014 (5)	0.0272 (5)	0.0044 (5)
C2	0.0561 (7)	0.0484 (7)	0.0580 (8)	−0.0117 (6)	0.0259 (6)	−0.0030 (6)
C3	0.0475 (6)	0.0582 (8)	0.0595 (8)	−0.0086 (6)	0.0216 (6)	−0.0022 (6)
C4	0.0502 (7)	0.0539 (7)	0.0453 (6)	−0.0042 (5)	0.0160 (5)	−0.0018 (5)
C4A	0.0526 (7)	0.0481 (7)	0.0410 (6)	−0.0042 (5)	0.0178 (5)	0.0003 (5)
C5	0.0599 (8)	0.0501 (7)	0.0503 (7)	0.0015 (6)	0.0214 (6)	0.0090 (5)
C6	0.0647 (8)	0.0506 (7)	0.0483 (7)	−0.0050 (6)	0.0246 (6)	0.0095 (5)
C6A	0.0554 (7)	0.0514 (7)	0.0405 (6)	−0.0081 (5)	0.0218 (5)	0.0006 (5)
C6B	0.0551 (7)	0.0593 (8)	0.0413 (6)	−0.0089 (6)	0.0216 (5)	−0.0007 (5)
C7	0.0614 (8)	0.0707 (9)	0.0519 (7)	−0.0122 (7)	0.0268 (6)	0.0055 (7)
C8	0.0588 (8)	0.0958 (12)	0.0556 (8)	−0.0151 (8)	0.0273 (7)	0.0064 (8)
C9	0.0526 (7)	0.0983 (13)	0.0605 (9)	0.0001 (8)	0.0268 (7)	0.0068 (8)
C10	0.0580 (8)	0.0713 (9)	0.0593 (8)	0.0015 (7)	0.0277 (6)	0.0046 (7)
C10A	0.0545 (7)	0.0574 (7)	0.0459 (6)	−0.0063 (6)	0.0241 (5)	−0.0014 (5)
C11A	0.0536 (7)	0.0455 (6)	0.0419 (6)	−0.0041 (5)	0.0208 (5)	−0.0009 (5)
C11B	0.0537 (7)	0.0436 (6)	0.0413 (6)	−0.0071 (5)	0.0205 (5)	−0.0009 (4)
C14	0.0527 (7)	0.0678 (9)	0.0709 (9)	0.0052 (7)	0.0210 (7)	0.0094 (7)
C18	0.0691 (10)	0.137 (2)	0.0963 (14)	−0.0196 (12)	0.0406 (10)	0.0270 (14)

Geometric parameters (Å, º) top

O1—C2	1.367 (2)	C8—C18	1.515 (3)
O1—C11B	1.3717 (16)	C9—C10	1.382 (3)
O2—C2	1.2132 (18)	C10—C10A	1.391 (2)
N11—C10A	1.378 (2)	C11A—C11B	1.387 (2)
N11—C11A	1.3730 (19)	C3—H3	0.9300
N11—H11	0.86 (2)	C5—H5	0.9300
C2—C3	1.433 (2)	C6—H6	0.9300
C3—C4	1.347 (2)	C7—H7	0.9300
C4—C4A	1.444 (2)	C9—H9	0.9300
C4—C14	1.500 (2)	C10—H10	0.9300
C4A—C11B	1.3927 (19)	C14—H14A	0.9600
C4A—C5	1.418 (2)	C14—H14B	0.9600
C5—C6	1.368 (2)	C14—H14C	0.9600
C6—C6A	1.400 (2)	C18—H18A	0.9600
C6A—C11A	1.4093 (19)	C18—H18B	0.9600
C6A—C6B	1.440 (2)	C18—H18C	0.9600
C6B—C7	1.399 (2)	C18—H18D	0.9600
C6B—C10A	1.4066 (19)	C18—H18E	0.9600
C7—C8	1.382 (3)	C18—H18F	0.9600
C8—C9	1.400 (3)

O1···N11	2.8837 (19)	C5···H14C	2.9600
O2···N11ⁱ	2.8136 (17)	C5···H14B	2.9600
O2···C14ⁱⁱ	3.338 (2)	C6A···H6^v	2.8500
O1···H11	2.77 (2)	C6B···H5^v	3.0800
O2···H14Bⁱⁱ	2.3900	C9···H14C^v	2.8600
O2···H10ⁱ	2.9000	C11A···H6^v	2.9700
O2···H11ⁱ	2.01 (2)	C14···H5	2.6900
N11···O1	2.8837 (19)	C18···H3^vii	2.9600
N11···O2ⁱ	2.8136 (17)	H3···H14A	2.2700
N11···C4ⁱⁱⁱ	3.3621 (17)	H3···C18^viii	2.9600
C2···C6ⁱⁱⁱ	3.548 (2)	H3···H18A^viii	2.4900
C2···C6Aⁱⁱⁱ	3.2532 (19)	H3···H18E^viii	2.4200
C2···C6Bⁱⁱⁱ	3.436 (2)	H5···C14	2.6900
C3···C10Aⁱⁱⁱ	3.3608 (19)	H5···H14B	2.5000
C3···C6Bⁱⁱⁱ	3.3546 (19)	H5···H14C	2.5100
C4···N11ⁱⁱⁱ	3.3621 (17)	H5···C6B^iv	3.0800
C4···C10Aⁱⁱⁱ	3.4985 (18)	H6···C6A^iv	2.8500
C4A···C11Aⁱⁱⁱ	3.5450 (18)	H6···C11A^iv	2.9700
C5···C10A^iv	3.5003 (18)	H7···H18D	2.3600
C6···C6A^iv	3.5963 (19)	H9···H18A	2.3300
C6···C11A^iv	3.5463 (19)	H9···H9^ix	2.5800
C6···C2ⁱⁱⁱ	3.548 (2)	H10···O2ⁱ	2.9000
C6A···C6^v	3.5963 (19)	H11···O1	2.77 (2)
C6A···C2ⁱⁱⁱ	3.2532 (19)	H11···O2ⁱ	2.01 (2)
C6B···C2ⁱⁱⁱ	3.436 (2)	H11···C2ⁱ	3.08 (2)
C6B···C3ⁱⁱⁱ	3.3546 (19)	H14A···H3	2.2700
C10A···C4ⁱⁱⁱ	3.4985 (18)	H14B···O2^vi	2.3900
C10A···C3ⁱⁱⁱ	3.3608 (19)	H14B···C5	2.9600
C10A···C5^v	3.5003 (18)	H14B···H5	2.5000
C11A···C6^v	3.5463 (19)	H14C···C5	2.9600
C11A···C11Bⁱⁱⁱ	3.4692 (18)	H14C···H5	2.5100
C11A···C4Aⁱⁱⁱ	3.5450 (18)	H14C···C9^iv	2.8600
C11B···C11Bⁱⁱⁱ	3.3601 (16)	H18A···H9	2.3300
C11B···C11Aⁱⁱⁱ	3.4692 (18)	H18A···H3^vii	2.4900
C14···O2^vi	3.338 (2)	H18B···C3^iv	2.9400
C2···H11ⁱ	3.08 (2)	H18D···H7	2.3600
C3···H18B^v	2.9400	H18E···H3^vii	2.4200

C2—O1—C11B	120.41 (11)	C4—C3—H3	119.00
C10A—N11—C11A	108.09 (12)	C4A—C5—H5	119.00
C11A—N11—H11	126.9 (14)	C6—C5—H5	119.00
C10A—N11—H11	124.3 (14)	C5—C6—H6	120.00
O1—C2—C3	117.55 (13)	C6A—C6—H6	120.00
O1—C2—O2	117.06 (14)	C6B—C7—H7	120.00
O2—C2—C3	125.38 (17)	C8—C7—H7	120.00
C2—C3—C4	122.99 (16)	C8—C9—H9	119.00
C4A—C4—C14	120.98 (13)	C10—C9—H9	119.00
C3—C4—C14	120.22 (15)	C9—C10—H10	122.00
C3—C4—C4A	118.81 (13)	C10A—C10—H10	122.00
C4—C4A—C5	124.12 (13)	C4—C14—H14A	109.00
C4—C4A—C11B	117.05 (12)	C4—C14—H14B	109.00
C5—C4A—C11B	118.82 (14)	C4—C14—H14C	109.00
C4A—C5—C6	121.36 (13)	H14A—C14—H14B	109.00
C5—C6—C6A	119.64 (13)	H14A—C14—H14C	109.00
C6—C6A—C11A	119.71 (14)	H14B—C14—H14C	109.00
C6B—C6A—C11A	105.55 (12)	C8—C18—H18A	109.00
C6—C6A—C6B	134.74 (13)	C8—C18—H18B	109.00
C7—C6B—C10A	119.59 (15)	C8—C18—H18C	109.00
C6A—C6B—C7	133.48 (14)	C8—C18—H18D	109.00
C6A—C6B—C10A	106.92 (13)	C8—C18—H18E	109.00
C6B—C7—C8	119.48 (17)	C8—C18—H18F	109.00
C9—C8—C18	119.98 (17)	H18A—C18—H18B	109.00
C7—C8—C18	120.65 (19)	H18A—C18—H18C	109.00
C7—C8—C9	119.36 (17)	H18A—C18—H18D	141.00
C8—C9—C10	122.95 (17)	H18A—C18—H18E	56.00
C9—C10—C10A	116.87 (17)	H18A—C18—H18F	56.00
N11—C10A—C10	128.99 (14)	H18B—C18—H18C	109.00
N11—C10A—C6B	109.27 (13)	H18B—C18—H18D	56.00
C6B—C10A—C10	121.74 (15)	H18B—C18—H18E	141.00
N11—C11A—C11B	129.60 (12)	H18B—C18—H18F	56.00
C6A—C11A—C11B	120.23 (12)	H18C—C18—H18D	56.00
N11—C11A—C6A	110.17 (13)	H18C—C18—H18E	56.00
C4A—C11B—C11A	120.23 (12)	H18C—C18—H18F	141.00
O1—C11B—C4A	123.06 (13)	H18D—C18—H18E	109.00
O1—C11B—C11A	116.71 (12)	H18D—C18—H18F	109.00
C2—C3—H3	118.00	H18E—C18—H18F	109.00

C11B—O1—C2—O2	176.99 (12)	C6—C6A—C6B—C7	−1.0 (3)
C11B—O1—C2—C3	−4.14 (18)	C6—C6A—C6B—C10A	−179.50 (15)
C2—O1—C11B—C4A	2.84 (18)	C11A—C6A—C6B—C7	178.38 (15)
C2—O1—C11B—C11A	−176.72 (12)	C11A—C6A—C6B—C10A	−0.12 (14)
C11A—N11—C10A—C6B	0.99 (15)	C6—C6A—C11A—N11	−179.77 (12)
C11A—N11—C10A—C10	−178.52 (14)	C6—C6A—C11A—C11B	0.25 (19)
C10A—N11—C11A—C6A	−1.08 (15)	C6B—C6A—C11A—N11	0.74 (15)
C10A—N11—C11A—C11B	178.89 (13)	C6B—C6A—C11A—C11B	−179.24 (12)
O1—C2—C3—C4	2.4 (2)	C6A—C6B—C7—C8	−178.08 (15)
O2—C2—C3—C4	−178.81 (15)	C10A—C6B—C7—C8	0.3 (2)
C2—C3—C4—C4A	0.7 (2)	C6A—C6B—C10A—N11	−0.53 (15)
C2—C3—C4—C14	−179.72 (14)	C6A—C6B—C10A—C10	179.03 (13)
C3—C4—C4A—C5	176.95 (13)	C7—C6B—C10A—N11	−179.27 (12)
C3—C4—C4A—C11B	−2.11 (19)	C7—C6B—C10A—C10	0.3 (2)
C14—C4—C4A—C5	−2.6 (2)	C6B—C7—C8—C9	−0.7 (2)
C14—C4—C4A—C11B	178.34 (13)	C6B—C7—C8—C18	178.49 (16)
C4—C4A—C5—C6	−179.13 (13)	C7—C8—C9—C10	0.6 (3)
C11B—C4A—C5—C6	−0.09 (19)	C18—C8—C9—C10	−178.59 (17)
C4—C4A—C11B—O1	0.40 (18)	C8—C9—C10—C10A	−0.1 (2)
C4—C4A—C11B—C11A	179.94 (13)	C9—C10—C10A—N11	179.08 (14)
C5—C4A—C11B—O1	−178.72 (11)	C9—C10—C10A—C6B	−0.4 (2)
C5—C4A—C11B—C11A	0.83 (18)	N11—C11A—C11B—O1	−1.3 (2)
C4A—C5—C6—C6A	−0.6 (2)	N11—C11A—C11B—C4A	179.12 (13)
C5—C6—C6A—C6B	179.79 (14)	C6A—C11A—C11B—O1	178.66 (11)
C5—C6—C6A—C11A	0.48 (19)	C6A—C11A—C11B—C4A	−0.91 (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, y−1/2, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, y−1, z; (vii) x−1/2, y−1/2, z; (viii) x+1/2, y+1/2, z; (ix) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O2ⁱ	0.86 (2)	2.01 (2)	2.814 (2)	154.5 (19)
C14—H14B···O2^vi	0.96	2.39	3.338 (2)	168
C6—H6···Cg1^iv	0.93	2.90	3.389 (1)	114
C5—H5···Cg2^iv	0.93	2.98	3.626 (1)	128

Symmetry codes: (i) −x+1/2, −y+5/2, −z; (iv) −x+1/2, y−1/2, −z+1/2; (vi) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO₂
M_r	263.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	26.8502 (4), 6.8202 (1), 15.8265 (3)
β (°)	115.531 (2)
V (Å³)	2615.21 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.48 × 0.45 × 0.18

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.313, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6122, 2703, 2218
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 1.07
No. of reflections	2703
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+1/2, −y+5/2, −z; (ii) x, y−1, z; (iii) −x+1/2, y−1/2, −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

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