3a,4,10,10b-Tetra­hydro-2H-furo[2,3-a]carbazol-5(3H)-one

Çaylak, N.; Hökelek, T.; Uludağ, N.; Patır, S.

doi:10.1107/S1600536807041608

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3a,4,10,10b-Tetrahydro-2H-furo[2,3-a]carbazol-5(3H)-one

N. Çaylak, T. Hökelek, N. Uludağ and S. Patır

The asymmetric unit of the title compound, C₁₄H₁₃NO₂, contains two independent molecules. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, the dihedral angles being 0.48 (17) and 1.26 (17)°. The cyclohexenone and tetrahydrofuran rings have envelope conformations. In the crystal structure, intermolecular N—H

O hydrogen bonds link the molecules into supramolecular chains nearly parallel to the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041608/xu2317sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041608/xu2317Isup2.hkl Contains datablock I

CCDC reference: 660370

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R factor = 0.059
wR factor = 0.169
Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.57
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.42 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.81 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C2'
PLAT245_ALERT_2_C U(iso) H6      Smaller than U(eq) C6      by ...       0.01 AngSq
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C14 H13 N O2

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C3A'   = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3A    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C10'   = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C10B   = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Phillipson & Zenk, 1980; Saxton, 1983; Abraham, 1975). The structures of tricyclic, tetracyclic and pentacyclic ring systems with dithiolane and other substituents of the tetrahydrocarbazole core, have been the subject of much interest in our laboratory. These include 1,2,3,4-tetrahydrocarbazole-1-spiro-2'-[1,3]dithiolane, (II) (Hökelek et al., 1994), N-(2-methoxyethyl)-N-{2,3,4,9-tetrahydrospiro[1H-carbazole-1, 2-(1,3)dithiolane]-4-yl}benzene-sulfonamide, (III) (Patır et al., 1997), spiro[carbazole-1(2H),2'-[1,3]-dithiolan]-4(3H)-one, (IV) (Hökelek et al., 1998), 9-acetonyl-3-ethylidene-1,2,3,4-tetrahydrospiro[carbazole-1,2'-[1,3] dithiolan]-4-one, (V) (Hökelek et al., 1999), N-(2,2-dimethoxyethyl)-N -{9-methoxymethyl-1,2,3,4-tetrahydrospiro[carbazole-1,2'-[1,3]dithiolan] -4-yl}benzamide, (VI) (Hökelek & Patir, 1999); also the pentacyclic compounds 6-ethyl-4-(2-methoxyethyl)-2,6-methano-5-oxo-hexahydropyrrolo- (2,3 - d)carbazole-1-spiro-2'-(1,3)dithiolane, (VII) (Hökelek & Patır, 2002), N-(2-benzyloxyethyl)-4,7-dimethyl-6-(1,3-dithiolan-2-yl)-1,2,3,4, 5,6-hexahydro-1,5-methano-2-azocino[4,3-b]indol-2-one, (VIII) (Hökelek et al., 2004) and 4-ethyl-6,6-ethylenedithio-2-(2-methoxyethyl)-7-methoxy- methylene-2,3,4,5,6,7-hexahydro-1,5-methano-1H-azocino[4,3-b]indol-3-one, (IX) (Hökelek et al., 2006). The title compound, (I), may be considered as a synthetic precursor of tetracyclic indole alkaloids of biological interests. The present study was undertaken to ascertain its crystal structure.

The asymmetric unit of the title compound, (I), contains two independent molecules (Fig. 1). It consists of a carbazole skeleton with furan ring, in which the bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds N10—C9A [1.388 (5) Å], N10—C10A [1.357 (5) Å], N10'-C9A' [1.378 (5) Å] and N10'-C10 [1.362 (5) Å] generally agree with those in compounds (II)-(IX). In all structures atom N10 is substituted. The absolute configurations of C3a and C10b are R and R, respectively.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C5b/C6—C9/C9a), B (C5a/C5b/C9a/N10/C10a) and A' (C5b'/C6'-C9'/C9a'), B' (C5a'/C5b'/C9a'/N10'/C10) are planar. They are also nearly coplanar with dihedral angles of A/B = 0.48 (17)° and A'/B' = 1.26 (17)°. Rings C (C3a/C4/C5/C5a/C10a/C10b), D (O1/C2/C3/C3a/C10b) and C' (C3a'/C4'/C5'/C5a'/C10/C10'), D' (O1'/C2'/C3'/C3a'/C10') have envelope conformations with atoms C3a and C3a' displaced by -0.472 (5) Å (for ring C), 0.533 (5) Å (for ring D) and -0.491 (5) Å (for ring C'), -0.551 (5) Å (for ring D') from the planes of the other ring atoms, respectively. Rings C and C' have pseudo mirror planes running through atoms C3a and C5a (for ring C) and C3a' and C5a' (for ring C'), while rings D and D' have pseudo twofold axis and pseudo mirror plane, respectively, running through atom C2 and midpoint of C3a—C10b bond (for ring D) and atom C3a' and midpoint of O1'-C2'bond (for ring D'), as can be deduced from the torsion angles (Table 1).

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 2) link the molecules into chains nearly parallel to c axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Phillipson & Zenk (1980); Saxton (1983); Abraham (1975). For related structures, see: Hökelek et al. (1994); Patır et al. (1997); Hökelek et al. (1998); Hökelek et al. (1999); Hökelek & Patir (1999); Hökelek & Patır (2002); Hökelek et al. (2004); Hökelek et al. (2006). For bond length data, see: Allen et al. (1987).

For related literature, see: Hökelek & Patir (1999).

Experimental top

For the preparation of the title compound, (I), a solution of 2,3-dichloro -5,6-dicyano-p-benzoquine (4.25 g, 18.75 mmol) in tetrahydrofuran (30 ml) was added dropwise to an ice cold solution of (3aS,10bR)-3,3a,4,5,10,10b -hexahydro-2H-furo[2,3-a]carbazole (2.00 g, 9.37 mmol) in tetrahydrofuran -water (90:10, 50 ml). The mixture was stirred in an ice bath for 4 h, and then over night. The mixture was poured into sodium hydroxide (100 ml, 10%) and extracted with dichloromethane (25 ml). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate (yield; 1.56 g, 73%).

Structure description top

For related literature, see: Hökelek & Patir (1999).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level. The hydrogen atoms are omitted for clarity.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted [symmetry code: (ii) 1 - x, 1 - y, 2 - z].

(3aR,10bR)-3a,4,10,10b-Tetrahydro-2H-furo[2,3-a]carbazol-5(3H)-one top

Crystal data top

C₁₄H₁₃NO₂	Z = 4
M_r = 227.26	F(000) = 480
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Melting point: 484 K
a = 9.5970 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0316 (3) Å	Cell parameters from 25 reflections
c = 12.4952 (3) Å	θ = 3.5–15.8°
α = 98.498 (15)°	µ = 0.09 mm⁻¹
β = 107.499 (18)°	T = 298 K
γ = 96.362 (19)°	Block, colorless
V = 1119.21 (16) Å³	0.25 × 0.20 × 0.15 mm

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	1657 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.1°, θ_min = 3.2°
non–profiled ω scans	h = −11→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.961, T_max = 0.985	l = 0→14
4127 measured reflections	3 standard reflections every 120 min
3933 independent reflections	intensity decay: 1%

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0695P)²] where P = (F_o² + 2F_c²)/3
3933 reflections	(Δ/σ)_max < 0.001
411 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂	γ = 96.362 (19)°
M_r = 227.26	V = 1119.21 (16) Å³
Triclinic, P1	Z = 4
a = 9.5970 (2) Å	Mo Kα radiation
b = 10.0316 (3) Å	µ = 0.09 mm⁻¹
c = 12.4952 (3) Å	T = 298 K
α = 98.498 (15)°	0.25 × 0.20 × 0.15 mm
β = 107.499 (18)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	1657 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.961, T_max = 0.985	3 standard reflections every 120 min
4127 measured reflections	intensity decay: 1%
3933 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.21 e Å⁻³
3933 reflections	Δρ_min = −0.22 e Å⁻³
411 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3614 (4)	0.0625 (3)	0.8096 (2)	0.0575 (9)
O2	0.4088 (4)	0.4281 (4)	1.1854 (3)	0.0780 (11)
N10	0.6324 (4)	0.2534 (4)	0.9325 (3)	0.0453 (10)
H10	0.654 (5)	0.195 (5)	0.874 (4)	0.088 (17)*
C2	0.3106 (7)	−0.0309 (5)	0.8735 (5)	0.0624 (15)
H21	0.392 (6)	−0.087 (5)	0.903 (4)	0.097 (19)*
H22	0.245 (7)	−0.121 (6)	0.816 (5)	0.13 (2)*
C3	0.2490 (8)	0.0502 (6)	0.9539 (5)	0.0661 (16)
H31	0.325 (7)	0.061 (6)	1.033 (6)	0.13 (3)*
H32	0.150 (5)	0.010 (5)	0.952 (4)	0.077 (17)*
C3A	0.2338 (6)	0.1863 (5)	0.9132 (4)	0.0535 (13)
H3A	0.131 (5)	0.171 (4)	0.849 (4)	0.062 (14)*
C4	0.2435 (6)	0.3072 (6)	1.0061 (4)	0.0557 (14)
H41	0.213 (6)	0.398 (6)	0.971 (4)	0.108 (19)*
H42	0.178 (5)	0.286 (5)	1.042 (4)	0.065 (15)*
C5	0.3954 (5)	0.3658 (5)	1.0900 (4)	0.0483 (12)
C5A	0.5185 (5)	0.3427 (4)	1.0513 (3)	0.0393 (11)
C5B	0.6747 (5)	0.3850 (4)	1.1055 (4)	0.0424 (11)
C6	0.7658 (6)	0.4656 (5)	1.2100 (4)	0.0508 (13)
H6	0.720 (4)	0.503 (4)	1.259 (3)	0.038 (12)*
C7	0.9151 (7)	0.4841 (6)	1.2311 (5)	0.0622 (15)
H7	0.973 (5)	0.542 (4)	1.295 (4)	0.053 (14)*
C8	0.9794 (7)	0.4263 (5)	1.1547 (5)	0.0628 (15)
H8	1.086 (6)	0.443 (5)	1.167 (4)	0.093 (19)*
C9	0.8942 (5)	0.3469 (5)	1.0509 (4)	0.0524 (13)
H9	0.940 (5)	0.302 (5)	0.997 (4)	0.087 (17)*
C9A	0.7427 (5)	0.3281 (4)	1.0291 (3)	0.0409 (11)
C10A	0.4989 (5)	0.2641 (4)	0.9463 (3)	0.0383 (11)
C10B	0.3547 (5)	0.1990 (5)	0.8586 (4)	0.0441 (12)
H10B	0.328 (6)	0.255 (5)	0.803 (4)	0.096 (19)*
O1'	0.8017 (4)	0.7748 (3)	1.4224 (2)	0.0590 (9)
O2'	0.7739 (4)	1.0773 (4)	1.8104 (3)	0.0793 (12)
N10'	0.6708 (4)	1.0219 (4)	1.4240 (3)	0.0455 (10)
H10'	0.666 (5)	0.988 (4)	1.358 (4)	0.062 (16)*
C2'	0.9560 (7)	0.7825 (9)	1.4831 (5)	0.0769 (19)
H21'	1.001 (8)	0.847 (7)	1.452 (6)	0.16 (3)*
H22'	0.973 (6)	0.681 (6)	1.467 (5)	0.11 (2)*
C3'	0.9758 (6)	0.8239 (6)	1.6083 (4)	0.0574 (14)
H31'	1.015 (5)	0.926 (5)	1.631 (4)	0.087 (18)*
H32'	1.053 (5)	0.771 (4)	1.655 (4)	0.063 (14)*
C3A'	0.8212 (5)	0.7840 (5)	1.6150 (4)	0.0477 (12)
H3A'	0.807 (5)	0.682 (5)	1.615 (4)	0.076 (15)*
C4'	0.7920 (8)	0.8567 (6)	1.7204 (5)	0.0607 (15)
H41'	0.705 (6)	0.813 (5)	1.717 (4)	0.08 (2)*
H42'	0.873 (6)	0.848 (5)	1.793 (5)	0.090 (18)*
C5'	0.7615 (5)	1.0012 (5)	1.7200 (4)	0.0521 (13)
C5A'	0.7197 (4)	1.0437 (4)	1.6119 (3)	0.0399 (11)
C5B'	0.6913 (4)	1.1738 (4)	1.5828 (3)	0.0410 (11)
C6'	0.6891 (5)	1.3000 (5)	1.6424 (4)	0.0468 (12)
H6'	0.707 (4)	1.323 (4)	1.717 (4)	0.052 (14)*
C7'	0.6594 (5)	1.4060 (5)	1.5852 (4)	0.0524 (13)
H7'	0.651 (4)	1.498 (4)	1.619 (3)	0.048 (12)*
C8'	0.6326 (6)	1.3864 (5)	1.4668 (5)	0.0591 (14)
H8'	0.608 (4)	1.467 (4)	1.423 (3)	0.060 (13)*
C9'	0.6346 (5)	1.2632 (5)	1.4058 (4)	0.0520 (13)
H9'	0.615 (4)	1.246 (4)	1.329 (3)	0.042 (12)*
C9A'	0.6622 (4)	1.1557 (4)	1.4631 (3)	0.0401 (11)
C10	0.7070 (4)	0.9548 (4)	1.5132 (4)	0.0409 (11)
C10'	0.7247 (5)	0.8092 (5)	1.5011 (4)	0.0452 (12)
H10A	0.624 (5)	0.758 (4)	1.476 (3)	0.052 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.079 (2)	0.050 (2)	0.0440 (19)	0.0092 (17)	0.0228 (17)	0.0041 (16)
O2	0.081 (3)	0.104 (3)	0.051 (2)	0.019 (2)	0.037 (2)	−0.014 (2)
N10	0.055 (3)	0.046 (2)	0.040 (2)	0.012 (2)	0.024 (2)	0.0056 (19)
C2	0.082 (4)	0.047 (3)	0.057 (3)	0.005 (3)	0.017 (3)	0.019 (3)
C3	0.072 (4)	0.063 (4)	0.069 (4)	0.001 (3)	0.032 (4)	0.020 (3)
C3A	0.052 (3)	0.061 (3)	0.050 (3)	0.011 (3)	0.017 (3)	0.017 (3)
C4	0.058 (4)	0.068 (4)	0.054 (3)	0.019 (3)	0.031 (3)	0.020 (3)
C5	0.061 (4)	0.054 (3)	0.042 (3)	0.023 (3)	0.027 (3)	0.013 (2)
C5A	0.054 (3)	0.038 (3)	0.033 (2)	0.014 (2)	0.023 (2)	0.007 (2)
C5B	0.055 (3)	0.040 (3)	0.040 (3)	0.016 (2)	0.024 (2)	0.010 (2)
C6	0.065 (4)	0.054 (3)	0.041 (3)	0.013 (3)	0.026 (3)	0.008 (2)
C7	0.066 (4)	0.064 (4)	0.046 (3)	0.008 (3)	0.011 (3)	−0.006 (3)
C8	0.055 (4)	0.067 (4)	0.066 (4)	0.013 (3)	0.020 (3)	0.006 (3)
C9	0.053 (4)	0.056 (3)	0.054 (3)	0.018 (3)	0.024 (3)	0.006 (3)
C9A	0.048 (3)	0.040 (3)	0.038 (3)	0.009 (2)	0.020 (2)	0.005 (2)
C10A	0.047 (3)	0.040 (3)	0.036 (3)	0.011 (2)	0.020 (2)	0.013 (2)
C10B	0.060 (3)	0.036 (3)	0.039 (3)	0.010 (2)	0.019 (3)	0.008 (2)
O1'	0.070 (3)	0.065 (2)	0.0415 (19)	0.0224 (18)	0.0193 (18)	−0.0018 (16)
O2'	0.134 (3)	0.083 (3)	0.045 (2)	0.050 (2)	0.049 (2)	0.0171 (19)
N10'	0.054 (3)	0.048 (3)	0.034 (2)	0.0126 (19)	0.016 (2)	0.004 (2)
C2'	0.067 (5)	0.110 (6)	0.055 (4)	0.028 (4)	0.024 (3)	0.004 (4)
C3'	0.052 (4)	0.059 (4)	0.060 (3)	0.017 (3)	0.017 (3)	0.003 (3)
C3A'	0.064 (4)	0.039 (3)	0.045 (3)	0.011 (2)	0.022 (2)	0.011 (2)
C4'	0.087 (5)	0.061 (4)	0.049 (3)	0.024 (4)	0.035 (3)	0.022 (3)
C5'	0.067 (3)	0.054 (3)	0.049 (3)	0.019 (3)	0.034 (3)	0.016 (3)
C5A'	0.049 (3)	0.038 (3)	0.035 (3)	0.005 (2)	0.019 (2)	0.003 (2)
C5B'	0.041 (3)	0.045 (3)	0.038 (3)	0.006 (2)	0.016 (2)	0.003 (2)
C6'	0.055 (3)	0.043 (3)	0.046 (3)	0.008 (2)	0.024 (3)	0.003 (3)
C7'	0.058 (3)	0.036 (3)	0.068 (4)	0.007 (2)	0.028 (3)	0.007 (3)
C8'	0.068 (4)	0.054 (4)	0.069 (4)	0.019 (3)	0.035 (3)	0.020 (3)
C9'	0.059 (3)	0.062 (4)	0.042 (3)	0.017 (3)	0.021 (3)	0.016 (3)
C9A'	0.044 (3)	0.045 (3)	0.036 (3)	0.012 (2)	0.018 (2)	0.008 (2)
C10	0.037 (3)	0.044 (3)	0.043 (3)	0.006 (2)	0.015 (2)	0.007 (2)
C10'	0.045 (3)	0.046 (3)	0.046 (3)	0.006 (3)	0.022 (3)	0.001 (2)

Geometric parameters (Å, º) top

O1—C2	1.451 (5)	O1'—C2'	1.434 (6)
O1—C10B	1.432 (5)	O1'—C10'	1.424 (5)
O2—C5	1.225 (5)	O2'—C5'	1.232 (5)
N10—C9A	1.388 (5)	N10'—C9A'	1.378 (5)
N10—C10A	1.357 (5)	N10'—C10	1.362 (5)
N10—H10	0.96 (5)	N10'—H10'	0.83 (4)
C2—H21	1.03 (5)	C2'—H21'	0.93 (7)
C2—H22	1.07 (6)	C2'—H22'	1.05 (6)
C3—C2	1.498 (7)	C3'—C2'	1.507 (7)
C3—H31	1.02 (6)	C3'—H31'	1.02 (5)
C3—H32	0.98 (5)	C3'—H32'	1.04 (4)
C3A—C3	1.532 (7)	C3A'—C3'	1.524 (6)
C3A—H3A	1.05 (4)	C3A'—C4'	1.526 (6)
C3A—C4	1.524 (7)	C3A'—C10'	1.520 (6)
C4—H41	1.10 (6)	C3A'—H3A'	1.02 (5)
C4—H42	0.90 (4)	C4'—H41'	0.88 (5)
C5—C4	1.510 (7)	C4'—H42'	1.03 (5)
C5A—C5	1.433 (5)	C5'—C4'	1.510 (7)
C5A—C5B	1.432 (6)	C5A'—C5'	1.432 (6)
C5A—C10A	1.375 (5)	C5A'—C10	1.375 (5)
C5B—C6	1.403 (6)	C5B'—C5A'	1.439 (6)
C6—C7	1.362 (7)	C5B'—C6'	1.376 (6)
C6—H6	0.91 (4)	C5B'—C9A'	1.416 (5)
C7—C8	1.378 (7)	C6'—H6'	0.88 (4)
C7—H7	0.90 (4)	C7'—C6'	1.376 (6)
C8—H8	0.98 (5)	C7'—C8'	1.403 (6)
C9—C8	1.377 (6)	C7'—H7'	0.98 (4)
C9—H9	0.99 (5)	C8'—H8'	1.05 (4)
C9A—C5B	1.399 (5)	C9A'—C9'	1.387 (6)
C9A—C9	1.382 (6)	C9'—C8'	1.358 (6)
C10A—C10B	1.490 (6)	C9'—H9'	0.90 (4)
C10B—C3A	1.515 (6)	C10—C10'	1.481 (6)
C10B—H10B	0.95 (5)	C10'—H10A	0.98 (4)

C10B—O1—C2	108.7 (3)	C9A'—N10'—H10'	126 (3)
C10A—N10—C9A	108.6 (3)	O1'—C2'—C3'	106.8 (4)
C10A—N10—H10	129 (3)	O1'—C2'—H22'	103 (3)
C9A—N10—H10	122 (3)	C3'—C2'—H22'	109 (3)
O1—C2—C3	107.2 (4)	O1'—C2'—H21'	103 (5)
O1—C2—H21	109 (3)	C3'—C2'—H21'	115 (5)
C3—C2—H21	121 (3)	H22'—C2'—H21'	118 (6)
O1—C2—H22	109 (3)	C2'—C3'—C3A'	103.6 (5)
C3—C2—H22	120 (3)	C2'—C3'—H32'	110 (2)
H21—C2—H22	89 (4)	C3A'—C3'—H32'	112 (2)
C2—C3—C3A	105.1 (4)	C2'—C3'—H31'	108 (3)
C2—C3—H32	115 (3)	C3A'—C3'—H31'	114 (3)
C3A—C3—H32	107 (3)	H32'—C3'—H31'	110 (4)
C2—C3—H31	106 (4)	C10'—C3A'—C3'	101.4 (4)
C3A—C3—H31	113 (4)	C10'—C3A'—C4'	115.4 (4)
H32—C3—H31	111 (4)	C3'—C3A'—C4'	115.6 (5)
C10B—C3A—C4	114.9 (4)	C10'—C3A'—H3A'	109 (3)
C10B—C3A—C3	101.8 (4)	C3'—C3A'—H3A'	107 (3)
C4—C3A—C3	114.8 (4)	C4'—C3A'—H3A'	108 (3)
C10B—C3A—H3A	109 (2)	C5'—C4'—C3A'	116.7 (4)
C4—C3A—H3A	110 (2)	C5'—C4'—H42'	113 (3)
C3—C3A—H3A	106 (2)	C3A'—C4'—H42'	110 (3)
C5—C4—C3A	116.7 (4)	C5'—C4'—H41'	102 (4)
C5—C4—H42	112 (3)	C3A'—C4'—H41'	104 (3)
C3A—C4—H42	109 (3)	H42'—C4'—H41'	111 (4)
C5—C4—H41	100 (3)	O2'—C5'—C5A'	122.7 (4)
C3A—C4—H41	113 (3)	O2'—C5'—C4'	120.0 (4)
H42—C4—H41	106 (4)	C5A'—C5'—C4'	117.2 (4)
O2—C5—C5A	123.5 (4)	C10—C5A'—C5'	120.6 (4)
O2—C5—C4	120.2 (4)	C10—C5A'—C5B'	108.1 (4)
C5A—C5—C4	116.3 (4)	C5'—C5A'—C5B'	131.2 (4)
C10A—C5A—C5B	106.9 (3)	C6'—C5B'—C9A'	119.1 (4)
C10A—C5A—C5	121.5 (4)	C6'—C5B'—C5A'	135.4 (4)
C5B—C5A—C5	131.5 (4)	C9A'—C5B'—C5A'	105.4 (3)
C9A—C5B—C6	118.0 (4)	C5B'—C6'—C7'	119.7 (5)
C9A—C5B—C5A	106.5 (4)	C5B'—C6'—H6'	127 (3)
C6—C5B—C5A	135.5 (4)	C7'—C6'—H6'	114 (3)
C7—C6—C5B	118.1 (5)	C6'—C7'—C8'	120.4 (5)
C7—C6—H6	125 (2)	C6'—C7'—H7'	126 (2)
C5B—C6—H6	117 (2)	C8'—C7'—H7'	113 (2)
C6—C7—C8	122.8 (5)	C9—C8—C7	121.1 (5)
C6—C7—H7	118 (3)	C9—C8—H8	115 (3)
C8—C7—H7	119 (3)	C7—C8—H8	124 (3)
C8—C9—C9A	116.4 (5)	C9'—C8'—C7'	121.2 (5)
C8—C9—H9	121 (3)	C9'—C8'—H8'	119 (2)
C9A—C9—H9	122 (3)	C7'—C8'—H8'	120 (2)
C9—C9A—N10	128.2 (4)	C8'—C9'—C9A'	118.5 (5)
C9—C9A—C5B	123.7 (4)	C8'—C9'—H9'	124 (2)
N10—C9A—C5B	108.1 (4)	C9A'—C9'—H9'	117 (2)
N10—C10A—C5A	109.9 (4)	N10'—C9A'—C9'	131.0 (4)
N10—C10A—C10B	123.7 (4)	N10'—C9A'—C5B'	107.8 (4)
C5A—C10A—C10B	126.4 (4)	C9'—C9A'—C5B'	121.1 (4)
O1—C10B—C10A	110.8 (4)	N10'—C10—C5A'	108.6 (4)
O1—C10B—C3A	105.8 (4)	N10'—C10—C10'	124.0 (4)
C10A—C10B—C3A	110.3 (4)	C5A'—C10—C10'	127.4 (4)
O1—C10B—H10B	113 (3)	O1'—C10'—C10	111.3 (4)
C10A—C10B—H10B	109 (3)	O1'—C10'—C3A'	105.5 (4)
C3A—C10B—H10B	107 (3)	C10—C10'—C3A'	109.1 (4)
C10'—O1'—C2'	109.8 (4)	O1'—C10'—H10A	112 (2)
C10—N10'—C9A'	110.0 (4)	C10—C10'—H10A	105 (2)
C10—N10'—H10'	123 (3)	C3A'—C10'—H10A	113 (2)

C10B—O1—C2—C3	8.7 (6)	C10'—O1'—C2'—C3'	0.3 (7)
C2—O1—C10B—C10A	92.5 (4)	C2'—O1'—C10'—C10	96.0 (5)
C2—O1—C10B—C3A	−27.2 (5)	C2'—O1'—C10'—C3A'	−22.3 (6)
C10A—N10—C9A—C9	−179.1 (4)	C10—N10'—C9A'—C9'	177.3 (4)
C10A—N10—C9A—C5B	0.9 (5)	C10—N10'—C9A'—C5B'	−1.3 (5)
C9A—N10—C10A—C5A	−1.0 (5)	C3A'—C3'—C2'—O1'	21.5 (7)
C9A—N10—C10A—C10B	178.8 (4)	C10'—C3A'—C4'—C5'	−39.9 (8)
C3A—C3—C2—O1	12.9 (7)	C3'—C3A'—C4'—C5'	78.2 (7)
C4—C3A—C3—C2	−152.8 (5)	C10'—C3A'—C3'—C2'	−33.5 (6)
C10B—C3A—C3—C2	−28.0 (6)	C4'—C3A'—C3'—C2'	−159.1 (5)
C10B—C3A—C4—C5	−42.7 (6)	C3'—C3A'—C10'—O1'	34.5 (4)
C3—C3A—C4—C5	74.9 (6)	C4'—C3A'—C10'—O1'	160.1 (4)
O2—C5—C4—C3A	−155.4 (4)	C3'—C3A'—C10'—C10	−85.3 (4)
C5A—C5—C4—C3A	24.1 (6)	C4'—C3A'—C10'—C10	40.4 (6)
C10A—C5A—C5—O2	175.4 (4)	O2'—C5'—C4'—C3A'	−161.7 (5)
C5B—C5A—C5—O2	−2.1 (7)	C5A'—C5'—C4'—C3A'	17.8 (8)
C10A—C5A—C5—C4	−4.1 (6)	C10—C5A'—C5'—O2'	−179.9 (5)
C5B—C5A—C5—C4	178.4 (4)	C5B'—C5A'—C5'—O2'	3.3 (8)
C10A—C5A—C5B—C9A	−0.2 (4)	C10—C5A'—C5'—C4'	0.6 (7)
C5—C5A—C5B—C9A	177.6 (4)	C5B'—C5A'—C5'—C4'	−176.2 (5)
C10A—C5A—C5B—C6	179.2 (5)	C5'—C5A'—C10—N10'	−178.1 (4)
C5—C5A—C5B—C6	−3.0 (8)	C5B'—C5A'—C10—N10'	−0.6 (5)
C5B—C5A—C10A—N10	0.7 (4)	C5'—C5A'—C10—C10'	3.5 (7)
C5—C5A—C10A—N10	−177.3 (4)	C5B'—C5A'—C10—C10'	−179.1 (4)
C5B—C5A—C10A—C10B	−179.1 (4)	C6'—C5B'—C5A'—C10	−179.1 (5)
C5—C5A—C10A—C10B	2.8 (6)	C9A'—C5B'—C5A'—C10	−0.2 (5)
C9A—C5B—C6—C7	0.1 (6)	C6'—C5B'—C5A'—C5'	−2.0 (8)
C5A—C5B—C6—C7	−179.3 (5)	C9A'—C5B'—C5A'—C5'	176.9 (4)
C5B—C6—C7—C8	−0.5 (8)	C9A'—C5B'—C6'—C7'	−0.2 (7)
C6—C7—C8—C9	0.7 (8)	C5A'—C5B'—C6'—C7'	178.6 (4)
C9A—C9—C8—C7	−0.5 (7)	C6'—C5B'—C9A'—N10'	−180.0 (4)
C9—C9A—C5B—C6	0.1 (6)	C5A'—C5B'—C9A'—N10'	0.9 (4)
N10—C9A—C5B—C6	−179.9 (4)	C6'—C5B'—C9A'—C9'	1.3 (6)
C9—C9A—C5B—C5A	179.6 (4)	C5A'—C5B'—C9A'—C9'	−177.9 (4)
N10—C9A—C5B—C5A	−0.4 (4)	C8'—C7'—C6'—C5B'	−0.5 (7)
N10—C9A—C9—C8	−179.9 (4)	C6'—C7'—C8'—C9'	0.3 (7)
C5B—C9A—C9—C8	0.2 (7)	C9A'—C9'—C8'—C7'	0.7 (7)
N10—C10A—C10B—O1	42.9 (6)	N10'—C9A'—C9'—C8'	−180.0 (4)
C5A—C10A—C10B—O1	−137.3 (4)	C5B'—C9A'—C9'—C8'	−1.5 (7)
N10—C10A—C10B—C3A	159.8 (4)	N10'—C10—C10'—O1'	41.6 (6)
C5A—C10A—C10B—C3A	−20.4 (6)	C5A'—C10—C10'—O1'	−140.2 (4)
O1—C10B—C3A—C4	158.5 (4)	N10'—C10—C10'—C3A'	157.7 (4)
C10A—C10B—C3A—C4	38.6 (6)	C5A'—C10—C10'—C3A'	−24.1 (6)
O1—C10B—C3A—C3	33.8 (5)	C9A'—N10'—C10—C5A'	1.2 (5)
C10A—C10B—C3A—C3	−86.1 (5)	C9A'—N10'—C10—C10'	179.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O2ⁱ	0.96 (5)	1.98 (6)	2.876 (6)	155 (4)
N10′—H10′···O1ⁱⁱ	0.83 (5)	2.01 (5)	2.829 (5)	169 (4)

Symmetry codes: (i) x, y−1, z−1; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.5970 (2), 10.0316 (3), 12.4952 (3)
α, β, γ (°)	98.498 (15), 107.499 (18), 96.362 (19)
V (Å³)	1119.21 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.961, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4127, 3933, 1657
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.169, 0.96
No. of reflections	3933
No. of parameters	411
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected torsion angles (º) top

C10B—O1—C2—C3	8.7 (6)	C10'—O1'—C2'—C3'	0.3 (7)
C2—O1—C10B—C3A	−27.2 (5)	C2'—O1'—C10'—C3A'	−22.3 (6)
C3A—C3—C2—O1	12.9 (7)	C3A'—C3'—C2'—O1'	21.5 (7)
C10B—C3A—C3—C2	−28.0 (6)	C10'—C3A'—C4'—C5'	−39.9 (8)
C10B—C3A—C4—C5	−42.7 (6)	C10'—C3A'—C3'—C2'	−33.5 (6)
C5A—C5—C4—C3A	24.1 (6)	C3'—C3A'—C10'—O1'	34.5 (4)
C10A—C5A—C5—C4	−4.1 (6)	C4'—C3A'—C10'—C10	40.4 (6)
C5—C5A—C10A—C10B	2.8 (6)	C5A'—C5'—C4'—C3A'	17.8 (8)
C5A—C10A—C10B—C3A	−20.4 (6)	C10—C5A'—C5'—C4'	0.6 (7)
C10A—C10B—C3A—C4	38.6 (6)	C5'—C5A'—C10—N10'	−178.1 (4)
O1—C10B—C3A—C3	33.8 (5)	C5A'—C10—C10'—C3A'	−24.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O2ⁱ	0.96 (5)	1.98 (6)	2.876 (6)	155 (4)
N10'—H10'···O1ⁱⁱ	0.83 (5)	2.01 (5)	2.829 (5)	169 (4)

Symmetry codes: (i) x, y−1, z−1; (ii) −x+1, −y+1, −z+2.

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