(E)-2-(Furan-2-yl­methyl­idene)-8-methyl-2,3,4,9-tetra­hydro-1H-carbazol-1-one

Archana, R.; Yamuna, E.; Rajendra Prasad, K.J.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536810045599

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3145

https://doi.org/10.1107/S1600536810045599

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(E)-2-(Furan-2-ylmethylidene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

R. Archana,^a E. Yamuna,^b K. J. Rajendra Prasad,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 3 November 2010; accepted 6 November 2010; online 13 November 2010)

In the title molecule, C₁₈H₁₅NO₂, the carbazole unit is not planar [maximum deviation from mean plane = 0.236 (2) Å]. The pyrrole ring makes dihedral angles of 1.21 (10) and 16.74 (12)° with the benzene and the furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(10) loops.

Related literature

For the synthesis of hetero-annulated carbazoles, see: Knölker & Reddy (2002 ). For the derivation of various hetero-annulated carbazoles, see: Sridharan et al. (2008 ); Danish & Rajendra Prasad (2004 , 2005 ); Periyasami et al. (2008 , 2009 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₅NO₂
M_r = 277.31
Orthorhombic, P b c a
a = 6.7353 (1) Å
b = 16.1393 (3) Å
c = 25.9549 (4) Å
V = 2821.38 (8) Å³
Z = 8
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 295 K
0.44 × 0.28 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.888, T_max = 1.000
6361 measured reflections
2736 independent reflections
2201 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.157
S = 1.05
2736 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1ⁱ	0.89 (3)	2.01 (3)	2.8969 (19)	176 (2)
Symmetry code: (i) -x+1, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045599/si2306sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045599/si2306Isup2.hkl

checkCIF report

Comment top

As a result of their significant potential as therapeutics, interest has grown in the development of methods for the efficient and rapid synthesis of the derivatives of various hetero-annulated carbazoles especially because the current methods, which involve multi-step reactions, lower yields, longer reaction times, and high cost of palladium (Knölker & Reddy (2002)) are unsatisfactory. Herein, therefore, we report the easily accessible synthon (E)-2-(furan-2-yl methylene)-8-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one to derive various hetero-annulated carbazoles (Sridharan et al., (2008); Danish & Rajendra Prasad (2004, 2005); Periyasami et al., (2008, 2009)).

In the title molecule (Scheme I, Fig. 1), C₁₈H₁₅NO₂, the carbazole unit is not planar. The pyrrole ring makes dihedral angles of 1.21 (10)° and 16.74 (12)° with the benzene and the furan rings respectively. The cyclohexene ring adopts a half-chair conformation. The puckering parameters (Cremer & Pople, 1975) are q2=0.232 (2) Å, q3=-0.153 (2) Å, Q=0.278 (2) Å, θ=123.4 (4)° and φ=322.6 (5)°. Intermolecular N9—H9···O1 hydrogen bonds form a R₂²(10) (Bernstein et al., 1995) ring in the crystal structure (Table 1, Fig. 2).

Related literature top

For the synthesis of hetero-annulated carbazoles, see: Knölker & Reddy (2002). For the derivation of various hetero-annulated carbazoles, see: Sridharan et al. (2008); Danish & Rajendra Prasad (2004, 2005); Periyasami et al. (2008, 2009). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

An equimolar mixture of 8-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.995 g, 0.005 mol) and furan-2-carbaldehyde (0.41 ml, 0.005 mol) was treated with 25 ml of a 5% ethanolic potassium hydroxide solution and stirred for 6 h at room temperature. The product precipitated as a yellow crystalline mass, was filtered off and washed with 50% ethanol. A further crop of condensation product was obtained on neutralization with acetic acid and dilution with water. The product was recrystallized from methanol to yield 90% (1.246 g) of the title compound. The pure compound was recrystallized from EtOAc.

Structure description top

For the synthesis of hetero-annulated carbazoles, see: Knölker & Reddy (2002). For the derivation of various hetero-annulated carbazoles, see: Sridharan et al. (2008); Danish & Rajendra Prasad (2004, 2005); Periyasami et al. (2008, 2009). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); 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.
	Fig. 2. The molecular 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.

(E)-2-(Furan-2-ylmethylidene)-8-methyl-2,3,4,9-tetrahydro-1H- carbazol-1-one top

Crystal data top

C₁₈H₁₅NO₂	D_x = 1.306 Mg m⁻³
M_r = 277.31	Melting point: 505 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3160 reflections
a = 6.7353 (1) Å	θ = 4.4–72.5°
b = 16.1393 (3) Å	µ = 0.68 mm⁻¹
c = 25.9549 (4) Å	T = 295 K
V = 2821.38 (8) Å³	Prism, pale-yellow
Z = 8	0.44 × 0.28 × 0.12 mm
F(000) = 1168

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2736 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2201 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.5081 pixels mm^-1	θ_max = 72.7°, θ_min = 5.7°
ω scans	h = −5→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −19→13
T_min = 0.888, T_max = 1.000	l = −31→31
6361 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0921P)² + 0.408P] where P = (F_o² + 2F_c²)/3
2736 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₅NO₂	V = 2821.38 (8) Å³
M_r = 277.31	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 6.7353 (1) Å	µ = 0.68 mm⁻¹
b = 16.1393 (3) Å	T = 295 K
c = 25.9549 (4) Å	0.44 × 0.28 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2736 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2201 reflections with I > 2σ(I)
T_min = 0.888, T_max = 1.000	R_int = 0.026
6361 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.23 e Å⁻³
2736 reflections	Δρ_min = −0.26 e Å⁻³
195 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
O1	0.3691 (2)	0.06478 (9)	−0.04131 (5)	0.0638 (5)
O11	0.0871 (3)	0.21485 (11)	−0.18520 (6)	0.0810 (6)
N9	0.2678 (2)	0.02422 (9)	0.06403 (5)	0.0489 (4)
C1	0.2176 (3)	0.09332 (11)	−0.02148 (6)	0.0475 (5)
C2	0.0821 (2)	0.15134 (10)	−0.04916 (7)	0.0473 (5)
C3	−0.0829 (3)	0.19426 (12)	−0.01982 (8)	0.0605 (6)
C4	−0.1653 (3)	0.14925 (13)	0.02677 (8)	0.0615 (6)
C4A	−0.0102 (3)	0.10045 (11)	0.05422 (7)	0.0508 (5)
C4B	−0.0102 (3)	0.06700 (11)	0.10466 (7)	0.0537 (6)
C5	−0.1417 (3)	0.07341 (14)	0.14698 (8)	0.0679 (7)
C6	−0.0955 (4)	0.03192 (16)	0.19083 (9)	0.0735 (8)
C7	0.0762 (3)	−0.01716 (14)	0.19432 (8)	0.0681 (7)
C8	0.2108 (3)	−0.02535 (12)	0.15467 (7)	0.0561 (6)
C8A	0.1646 (3)	0.01922 (10)	0.10952 (6)	0.0497 (5)
C9A	0.1612 (3)	0.07363 (10)	0.03084 (6)	0.0466 (5)
C10	0.1218 (3)	0.16433 (11)	−0.09919 (7)	0.0518 (5)
C12	−0.0226 (4)	0.27239 (15)	−0.21183 (9)	0.0775 (8)
C13	−0.1434 (4)	0.31065 (15)	−0.18050 (9)	0.0736 (8)
C14	−0.1132 (3)	0.27681 (12)	−0.13083 (7)	0.0586 (6)
C15	0.0280 (3)	0.21920 (11)	−0.13515 (7)	0.0551 (6)
C18	0.3917 (3)	−0.07814 (15)	0.15847 (8)	0.0718 (8)
H3A	−0.19153	0.20433	−0.04355	0.0725*
H3B	−0.03417	0.24784	−0.00856	0.0725*
H4A	−0.22223	0.18937	0.05035	0.0738*
H4B	−0.27067	0.11228	0.01579	0.0738*
H5	−0.25654	0.10519	0.14480	0.0815*
H6	−0.17930	0.03607	0.21919	0.0882*
H7	0.10015	−0.04552	0.22489	0.0818*
H9	0.382 (4)	−0.0012 (13)	0.0577 (9)	0.063 (6)*
H10	0.22576	0.13304	−0.11252	0.0622*
H12	−0.01222	0.28261	−0.24699	0.0931*
H13	−0.23267	0.35233	−0.18921	0.0884*
H14	−0.17937	0.29187	−0.10080	0.0704*
H18A	0.39152	−0.10687	0.19085	0.1077*
H18B	0.50785	−0.04389	0.15617	0.1077*
H18C	0.39214	−0.11766	0.13083	0.1077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0598 (8)	0.0799 (9)	0.0517 (7)	0.0239 (7)	0.0087 (6)	0.0061 (6)
O11	0.0930 (12)	0.0872 (11)	0.0627 (9)	0.0242 (9)	0.0049 (8)	0.0038 (8)
N9	0.0503 (8)	0.0537 (8)	0.0428 (7)	0.0025 (7)	0.0021 (6)	−0.0015 (6)
C1	0.0486 (9)	0.0478 (9)	0.0460 (9)	0.0025 (7)	0.0006 (7)	−0.0052 (7)
C2	0.0471 (9)	0.0464 (8)	0.0485 (9)	0.0012 (7)	−0.0018 (7)	−0.0039 (7)
C3	0.0562 (10)	0.0619 (11)	0.0633 (12)	0.0158 (9)	0.0043 (9)	0.0010 (9)
C4	0.0534 (10)	0.0664 (11)	0.0647 (12)	0.0118 (9)	0.0092 (9)	−0.0047 (9)
C4A	0.0500 (9)	0.0496 (9)	0.0528 (10)	−0.0019 (7)	0.0042 (7)	−0.0084 (8)
C4B	0.0550 (10)	0.0557 (10)	0.0503 (10)	−0.0077 (8)	0.0080 (8)	−0.0092 (8)
C5	0.0656 (12)	0.0755 (13)	0.0627 (12)	−0.0084 (10)	0.0200 (10)	−0.0104 (10)
C6	0.0797 (15)	0.0856 (15)	0.0553 (12)	−0.0232 (12)	0.0225 (11)	−0.0094 (11)
C7	0.0816 (15)	0.0771 (13)	0.0457 (10)	−0.0289 (12)	0.0024 (10)	0.0011 (9)
C8	0.0672 (11)	0.0566 (10)	0.0444 (9)	−0.0180 (9)	−0.0046 (8)	−0.0018 (8)
C8A	0.0546 (9)	0.0514 (9)	0.0431 (9)	−0.0118 (8)	0.0025 (7)	−0.0072 (7)
C9A	0.0491 (8)	0.0462 (8)	0.0446 (9)	0.0009 (7)	−0.0007 (7)	−0.0055 (7)
C10	0.0548 (9)	0.0478 (9)	0.0529 (10)	0.0049 (8)	−0.0025 (8)	−0.0045 (7)
C12	0.0962 (16)	0.0823 (14)	0.0541 (12)	0.0093 (13)	−0.0067 (12)	0.0136 (11)
C13	0.0794 (14)	0.0662 (13)	0.0753 (15)	0.0177 (11)	−0.0178 (12)	0.0001 (11)
C14	0.0643 (11)	0.0643 (11)	0.0473 (10)	0.0131 (9)	−0.0024 (8)	−0.0073 (8)
C15	0.0623 (10)	0.0526 (9)	0.0505 (10)	−0.0036 (8)	−0.0064 (8)	−0.0008 (8)
C18	0.0778 (14)	0.0819 (15)	0.0556 (12)	−0.0085 (12)	−0.0087 (10)	0.0123 (10)

Geometric parameters (Å, º) top

O1—C1	1.232 (2)	C8—C8A	1.410 (2)
O11—C12	1.373 (3)	C10—C15	1.433 (3)
O11—C15	1.361 (2)	C12—C13	1.306 (4)
N9—C8A	1.373 (2)	C13—C14	1.415 (3)
N9—C9A	1.376 (2)	C14—C15	1.335 (3)
N9—H9	0.89 (3)	C3—H3A	0.9700
C1—C2	1.492 (2)	C3—H3B	0.9700
C1—C9A	1.446 (2)	C4—H4A	0.9700
C2—C3	1.515 (3)	C4—H4B	0.9700
C2—C10	1.342 (3)	C5—H5	0.9300
C3—C4	1.516 (3)	C6—H6	0.9300
C4—C4A	1.490 (3)	C7—H7	0.9300
C4A—C9A	1.374 (3)	C10—H10	0.9300
C4A—C4B	1.416 (3)	C12—H12	0.9300
C4B—C5	1.415 (3)	C13—H13	0.9300
C4B—C8A	1.413 (3)	C14—H14	0.9300
C5—C6	1.357 (3)	C18—H18A	0.9600
C6—C7	1.405 (3)	C18—H18B	0.9600
C7—C8	1.378 (3)	C18—H18C	0.9600
C8—C18	1.490 (3)

O1···N9	2.8930 (19)	C14···H5ⁱⁱⁱ	3.0900
O1···N9ⁱ	2.8969 (19)	C14···H3A	2.6000
O11···C7ⁱⁱ	3.383 (3)	C15···H3A	2.8100
O1···H9	2.78 (2)	C18···H9	2.90 (2)
O1···H9ⁱ	2.01 (3)	C18···H10ⁱ	2.9700
O1···H10	2.3600	H3A···C14	2.6000
N9···O1	2.8930 (19)	H3A···C15	2.8100
N9···O1ⁱ	2.8969 (19)	H3A···H14	2.0500
C1···C4Aⁱⁱ	3.529 (3)	H3B···C4ⁱⁱⁱ	3.0300
C2···C8Aⁱⁱ	3.577 (2)	H3B···H4Aⁱⁱⁱ	2.5700
C3···C14	3.181 (3)	H4A···C2^iv	2.8900
C4A···C1ⁱⁱ	3.529 (3)	H4A···C10^iv	2.8800
C7···O11ⁱⁱ	3.383 (3)	H4A···H3B^iv	2.5700
C8···C15ⁱⁱ	3.554 (3)	H5···C13^iv	3.0800
C8···C10ⁱⁱ	3.482 (3)	H5···C14^iv	3.0900
C8A···C10ⁱⁱ	3.545 (3)	H6···C7^vii	2.9100
C8A···C2ⁱⁱ	3.577 (2)	H6···H7^vii	2.4600
C8A···C13ⁱⁱⁱ	3.550 (3)	H7···H18A	2.3700
C9A···C9Aⁱⁱ	3.595 (2)	H7···H6^vi	2.4600
C10···C8Aⁱⁱ	3.545 (3)	H9···O1	2.78 (2)
C10···C8ⁱⁱ	3.482 (3)	H9···C18	2.90 (2)
C13···C8A^iv	3.550 (3)	H9···O1ⁱ	2.01 (3)
C14···C3	3.181 (3)	H10···O1	2.3600
C15···C8ⁱⁱ	3.554 (3)	H10···C18ⁱ	2.9700
C2···H4Aⁱⁱⁱ	2.8900	H10···H18Bⁱ	2.5600
C3···H14	2.7100	H13···C6^iv	3.0800
C4···H3B^iv	3.0300	H13···C7^iv	2.9600
C4A···H14ⁱⁱⁱ	3.0700	H13···C8^iv	2.9600
C5···H18B^v	3.0400	H13···C8A^iv	3.0100
C6···H18B^v	3.0700	H14···C3	2.7100
C6···H13ⁱⁱⁱ	3.0800	H14···H3A	2.0500
C7···H6^vi	2.9100	H14···C4A^iv	3.0700
C7···H13ⁱⁱⁱ	2.9600	H14···C9A^iv	3.0300
C8···H13ⁱⁱⁱ	2.9600	H18A···H7	2.3700
C8A···H13ⁱⁱⁱ	3.0100	H18B···C5^viii	3.0400
C9A···H14ⁱⁱⁱ	3.0300	H18B···C6^viii	3.0700
C10···H4Aⁱⁱⁱ	2.8800	H18B···H10ⁱ	2.5600
C13···H5ⁱⁱⁱ	3.0800

C12—O11—C15	106.75 (18)	C10—C15—C14	133.61 (18)
C8A—N9—C9A	107.96 (14)	O11—C15—C10	117.45 (17)
C9A—N9—H9	127.2 (15)	O11—C15—C14	108.94 (17)
C8A—N9—H9	124.8 (15)	C2—C3—H3A	108.00
O1—C1—C9A	121.86 (17)	C2—C3—H3B	108.00
O1—C1—C2	122.69 (15)	C4—C3—H3A	108.00
C2—C1—C9A	115.44 (16)	C4—C3—H3B	108.00
C3—C2—C10	124.13 (16)	H3A—C3—H3B	107.00
C1—C2—C3	119.58 (16)	C3—C4—H4A	109.00
C1—C2—C10	116.23 (15)	C3—C4—H4B	109.00
C2—C3—C4	116.77 (16)	C4A—C4—H4A	109.00
C3—C4—C4A	112.22 (17)	C4A—C4—H4B	109.00
C4B—C4A—C9A	106.75 (16)	H4A—C4—H4B	108.00
C4—C4A—C4B	130.07 (18)	C4B—C5—H5	121.00
C4—C4A—C9A	122.99 (16)	C6—C5—H5	121.00
C5—C4B—C8A	119.49 (17)	C5—C6—H6	119.00
C4A—C4B—C5	133.62 (19)	C7—C6—H6	119.00
C4A—C4B—C8A	106.89 (16)	C6—C7—H7	118.00
C4B—C5—C6	118.1 (2)	C8—C7—H7	118.00
C5—C6—C7	121.4 (2)	C2—C10—H10	115.00
C6—C7—C8	123.2 (2)	C15—C10—H10	115.00
C7—C8—C8A	115.26 (18)	O11—C12—H12	125.00
C8A—C8—C18	121.82 (17)	C13—C12—H12	125.00
C7—C8—C18	122.92 (18)	C12—C13—H13	126.00
N9—C8A—C8	129.29 (17)	C14—C13—H13	126.00
C4B—C8A—C8	122.45 (17)	C13—C14—H14	126.00
N9—C8A—C4B	108.25 (14)	C15—C14—H14	126.00
C1—C9A—C4A	124.50 (17)	C8—C18—H18A	109.00
N9—C9A—C1	125.34 (17)	C8—C18—H18B	109.00
N9—C9A—C4A	110.15 (14)	C8—C18—H18C	109.00
C2—C10—C15	129.69 (17)	H18A—C18—H18B	109.00
O11—C12—C13	110.0 (2)	H18A—C18—H18C	109.00
C12—C13—C14	107.2 (2)	H18B—C18—H18C	109.00
C13—C14—C15	107.15 (18)

C15—O11—C12—C13	0.0 (3)	C9A—C4A—C4B—C8A	−0.8 (2)
C12—O11—C15—C10	179.89 (19)	C4—C4A—C9A—N9	−174.75 (17)
C12—O11—C15—C14	0.2 (2)	C4—C4A—C9A—C1	4.0 (3)
C9A—N9—C8A—C4B	−0.28 (19)	C4B—C4A—C9A—N9	0.6 (2)
C9A—N9—C8A—C8	178.49 (18)	C4B—C4A—C9A—C1	179.32 (17)
C8A—N9—C9A—C1	−178.91 (17)	C4A—C4B—C5—C6	179.8 (2)
C8A—N9—C9A—C4A	−0.2 (2)	C8A—C4B—C5—C6	−1.0 (3)
O1—C1—C2—C3	−170.47 (17)	C4A—C4B—C8A—N9	0.7 (2)
O1—C1—C2—C10	7.0 (3)	C4A—C4B—C8A—C8	−178.22 (17)
C9A—C1—C2—C3	8.5 (2)	C5—C4B—C8A—N9	−178.77 (17)
C9A—C1—C2—C10	−174.06 (16)	C5—C4B—C8A—C8	2.4 (3)
O1—C1—C9A—N9	1.6 (3)	C4B—C5—C6—C7	−0.9 (3)
O1—C1—C9A—C4A	−176.90 (18)	C5—C6—C7—C8	1.5 (4)
C2—C1—C9A—N9	−177.39 (15)	C6—C7—C8—C8A	−0.1 (3)
C2—C1—C9A—C4A	4.1 (3)	C6—C7—C8—C18	−179.4 (2)
C1—C2—C3—C4	−28.3 (2)	C7—C8—C8A—N9	179.62 (18)
C10—C2—C3—C4	154.45 (18)	C7—C8—C8A—C4B	−1.8 (3)
C1—C2—C10—C15	−176.11 (18)	C18—C8—C8A—N9	−1.1 (3)
C3—C2—C10—C15	1.2 (3)	C18—C8—C8A—C4B	177.53 (18)
C2—C3—C4—C4A	33.9 (2)	C2—C10—C15—O11	−174.38 (19)
C3—C4—C4A—C4B	162.79 (19)	C2—C10—C15—C14	5.2 (4)
C3—C4—C4A—C9A	−23.0 (3)	O11—C12—C13—C14	−0.2 (3)
C4—C4A—C4B—C5	−6.5 (4)	C12—C13—C14—C15	0.4 (3)
C4—C4A—C4B—C8A	174.15 (19)	C13—C14—C15—O11	−0.4 (2)
C9A—C4A—C4B—C5	178.5 (2)	C13—C14—C15—C10	−180.0 (2)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x+1/2, −y+1/2, −z; (iv) x−1/2, −y+1/2, −z; (v) x−1, y, z; (vi) x+1/2, y, −z+1/2; (vii) x−1/2, y, −z+1/2; (viii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.89 (3)	2.01 (3)	2.8969 (19)	176 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅NO₂
M_r	277.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	6.7353 (1), 16.1393 (3), 25.9549 (4)
V (Å³)	2821.38 (8)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.44 × 0.28 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.888, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6361, 2736, 2201
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.157, 1.05
No. of reflections	2736
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1ⁱ	0.89 (3)	2.01 (3)	2.8969 (19)	176 (2)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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