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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041608/xu2317sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041608/xu2317Isup2.hkl
Contains datablock I

CCDC reference: 660370

Key indicators

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

checkCIF/PLATON results

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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%).

Refinement top

H atoms were located in difference syntheses and refined isotropically [N—H = 0.83 (4) and 0.96 (5) Å, Uiso(H) = 0.088 (17) and 0.062 (16) Å2; C—H = 0.88 (4)–1.10 (6) Å, Uiso(H) = 0.038 (12)–0.16 (3) Å2].

Structure description 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.

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).

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
[Figure 1] 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.
[Figure 2] 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
C14H13NO2Z = 4
Mr = 227.26F(000) = 480
Triclinic, P1Dx = 1.349 Mg m3
Hall symbol: -P 1Melting point: 484 K
a = 9.5970 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0316 (3) ÅCell parameters from 25 reflections
c = 12.4952 (3) Åθ = 3.5–15.8°
α = 98.498 (15)°µ = 0.09 mm1
β = 107.499 (18)°T = 298 K
γ = 96.362 (19)°Block, colorless
V = 1119.21 (16) Å30.25 × 0.20 × 0.15 mm
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer
1657 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.1°, θmin = 3.2°
non–profiled ω scansh = 1110
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.961, Tmax = 0.985l = 014
4127 measured reflections3 standard reflections every 120 min
3933 independent reflections intensity decay: 1%
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0695P)2]
where P = (Fo2 + 2Fc2)/3
3933 reflections(Δ/σ)max < 0.001
411 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C14H13NO2γ = 96.362 (19)°
Mr = 227.26V = 1119.21 (16) Å3
Triclinic, P1Z = 4
a = 9.5970 (2) ÅMo Kα radiation
b = 10.0316 (3) ŵ = 0.09 mm1
c = 12.4952 (3) ÅT = 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)
Rint = 0.032
Tmin = 0.961, Tmax = 0.9853 standard reflections every 120 min
4127 measured reflections intensity decay: 1%
3933 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.21 e Å3
3933 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
O10.3614 (4)0.0625 (3)0.8096 (2)0.0575 (9)
O20.4088 (4)0.4281 (4)1.1854 (3)0.0780 (11)
N100.6324 (4)0.2534 (4)0.9325 (3)0.0453 (10)
H100.654 (5)0.195 (5)0.874 (4)0.088 (17)*
C20.3106 (7)0.0309 (5)0.8735 (5)0.0624 (15)
H210.392 (6)0.087 (5)0.903 (4)0.097 (19)*
H220.245 (7)0.121 (6)0.816 (5)0.13 (2)*
C30.2490 (8)0.0502 (6)0.9539 (5)0.0661 (16)
H310.325 (7)0.061 (6)1.033 (6)0.13 (3)*
H320.150 (5)0.010 (5)0.952 (4)0.077 (17)*
C3A0.2338 (6)0.1863 (5)0.9132 (4)0.0535 (13)
H3A0.131 (5)0.171 (4)0.849 (4)0.062 (14)*
C40.2435 (6)0.3072 (6)1.0061 (4)0.0557 (14)
H410.213 (6)0.398 (6)0.971 (4)0.108 (19)*
H420.178 (5)0.286 (5)1.042 (4)0.065 (15)*
C50.3954 (5)0.3658 (5)1.0900 (4)0.0483 (12)
C5A0.5185 (5)0.3427 (4)1.0513 (3)0.0393 (11)
C5B0.6747 (5)0.3850 (4)1.1055 (4)0.0424 (11)
C60.7658 (6)0.4656 (5)1.2100 (4)0.0508 (13)
H60.720 (4)0.503 (4)1.259 (3)0.038 (12)*
C70.9151 (7)0.4841 (6)1.2311 (5)0.0622 (15)
H70.973 (5)0.542 (4)1.295 (4)0.053 (14)*
C80.9794 (7)0.4263 (5)1.1547 (5)0.0628 (15)
H81.086 (6)0.443 (5)1.167 (4)0.093 (19)*
C90.8942 (5)0.3469 (5)1.0509 (4)0.0524 (13)
H90.940 (5)0.302 (5)0.997 (4)0.087 (17)*
C9A0.7427 (5)0.3281 (4)1.0291 (3)0.0409 (11)
C10A0.4989 (5)0.2641 (4)0.9463 (3)0.0383 (11)
C10B0.3547 (5)0.1990 (5)0.8586 (4)0.0441 (12)
H10B0.328 (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)
C100.7070 (4)0.9548 (4)1.5132 (4)0.0409 (11)
C10'0.7247 (5)0.8092 (5)1.5011 (4)0.0452 (12)
H10A0.624 (5)0.758 (4)1.476 (3)0.052 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.079 (2)0.050 (2)0.0440 (19)0.0092 (17)0.0228 (17)0.0041 (16)
O20.081 (3)0.104 (3)0.051 (2)0.019 (2)0.037 (2)0.014 (2)
N100.055 (3)0.046 (2)0.040 (2)0.012 (2)0.024 (2)0.0056 (19)
C20.082 (4)0.047 (3)0.057 (3)0.005 (3)0.017 (3)0.019 (3)
C30.072 (4)0.063 (4)0.069 (4)0.001 (3)0.032 (4)0.020 (3)
C3A0.052 (3)0.061 (3)0.050 (3)0.011 (3)0.017 (3)0.017 (3)
C40.058 (4)0.068 (4)0.054 (3)0.019 (3)0.031 (3)0.020 (3)
C50.061 (4)0.054 (3)0.042 (3)0.023 (3)0.027 (3)0.013 (2)
C5A0.054 (3)0.038 (3)0.033 (2)0.014 (2)0.023 (2)0.007 (2)
C5B0.055 (3)0.040 (3)0.040 (3)0.016 (2)0.024 (2)0.010 (2)
C60.065 (4)0.054 (3)0.041 (3)0.013 (3)0.026 (3)0.008 (2)
C70.066 (4)0.064 (4)0.046 (3)0.008 (3)0.011 (3)0.006 (3)
C80.055 (4)0.067 (4)0.066 (4)0.013 (3)0.020 (3)0.006 (3)
C90.053 (4)0.056 (3)0.054 (3)0.018 (3)0.024 (3)0.006 (3)
C9A0.048 (3)0.040 (3)0.038 (3)0.009 (2)0.020 (2)0.005 (2)
C10A0.047 (3)0.040 (3)0.036 (3)0.011 (2)0.020 (2)0.013 (2)
C10B0.060 (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)
C100.037 (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—C21.451 (5)O1'—C2'1.434 (6)
O1—C10B1.432 (5)O1'—C10'1.424 (5)
O2—C51.225 (5)O2'—C5'1.232 (5)
N10—C9A1.388 (5)N10'—C9A'1.378 (5)
N10—C10A1.357 (5)N10'—C101.362 (5)
N10—H100.96 (5)N10'—H10'0.83 (4)
C2—H211.03 (5)C2'—H21'0.93 (7)
C2—H221.07 (6)C2'—H22'1.05 (6)
C3—C21.498 (7)C3'—C2'1.507 (7)
C3—H311.02 (6)C3'—H31'1.02 (5)
C3—H320.98 (5)C3'—H32'1.04 (4)
C3A—C31.532 (7)C3A'—C3'1.524 (6)
C3A—H3A1.05 (4)C3A'—C4'1.526 (6)
C3A—C41.524 (7)C3A'—C10'1.520 (6)
C4—H411.10 (6)C3A'—H3A'1.02 (5)
C4—H420.90 (4)C4'—H41'0.88 (5)
C5—C41.510 (7)C4'—H42'1.03 (5)
C5A—C51.433 (5)C5'—C4'1.510 (7)
C5A—C5B1.432 (6)C5A'—C5'1.432 (6)
C5A—C10A1.375 (5)C5A'—C101.375 (5)
C5B—C61.403 (6)C5B'—C5A'1.439 (6)
C6—C71.362 (7)C5B'—C6'1.376 (6)
C6—H60.91 (4)C5B'—C9A'1.416 (5)
C7—C81.378 (7)C6'—H6'0.88 (4)
C7—H70.90 (4)C7'—C6'1.376 (6)
C8—H80.98 (5)C7'—C8'1.403 (6)
C9—C81.377 (6)C7'—H7'0.98 (4)
C9—H90.99 (5)C8'—H8'1.05 (4)
C9A—C5B1.399 (5)C9A'—C9'1.387 (6)
C9A—C91.382 (6)C9'—C8'1.358 (6)
C10A—C10B1.490 (6)C9'—H9'0.90 (4)
C10B—C3A1.515 (6)C10—C10'1.481 (6)
C10B—H10B0.95 (5)C10'—H10A0.98 (4)
C10B—O1—C2108.7 (3)C9A'—N10'—H10'126 (3)
C10A—N10—C9A108.6 (3)O1'—C2'—C3'106.8 (4)
C10A—N10—H10129 (3)O1'—C2'—H22'103 (3)
C9A—N10—H10122 (3)C3'—C2'—H22'109 (3)
O1—C2—C3107.2 (4)O1'—C2'—H21'103 (5)
O1—C2—H21109 (3)C3'—C2'—H21'115 (5)
C3—C2—H21121 (3)H22'—C2'—H21'118 (6)
O1—C2—H22109 (3)C2'—C3'—C3A'103.6 (5)
C3—C2—H22120 (3)C2'—C3'—H32'110 (2)
H21—C2—H2289 (4)C3A'—C3'—H32'112 (2)
C2—C3—C3A105.1 (4)C2'—C3'—H31'108 (3)
C2—C3—H32115 (3)C3A'—C3'—H31'114 (3)
C3A—C3—H32107 (3)H32'—C3'—H31'110 (4)
C2—C3—H31106 (4)C10'—C3A'—C3'101.4 (4)
C3A—C3—H31113 (4)C10'—C3A'—C4'115.4 (4)
H32—C3—H31111 (4)C3'—C3A'—C4'115.6 (5)
C10B—C3A—C4114.9 (4)C10'—C3A'—H3A'109 (3)
C10B—C3A—C3101.8 (4)C3'—C3A'—H3A'107 (3)
C4—C3A—C3114.8 (4)C4'—C3A'—H3A'108 (3)
C10B—C3A—H3A109 (2)C5'—C4'—C3A'116.7 (4)
C4—C3A—H3A110 (2)C5'—C4'—H42'113 (3)
C3—C3A—H3A106 (2)C3A'—C4'—H42'110 (3)
C5—C4—C3A116.7 (4)C5'—C4'—H41'102 (4)
C5—C4—H42112 (3)C3A'—C4'—H41'104 (3)
C3A—C4—H42109 (3)H42'—C4'—H41'111 (4)
C5—C4—H41100 (3)O2'—C5'—C5A'122.7 (4)
C3A—C4—H41113 (3)O2'—C5'—C4'120.0 (4)
H42—C4—H41106 (4)C5A'—C5'—C4'117.2 (4)
O2—C5—C5A123.5 (4)C10—C5A'—C5'120.6 (4)
O2—C5—C4120.2 (4)C10—C5A'—C5B'108.1 (4)
C5A—C5—C4116.3 (4)C5'—C5A'—C5B'131.2 (4)
C10A—C5A—C5B106.9 (3)C6'—C5B'—C9A'119.1 (4)
C10A—C5A—C5121.5 (4)C6'—C5B'—C5A'135.4 (4)
C5B—C5A—C5131.5 (4)C9A'—C5B'—C5A'105.4 (3)
C9A—C5B—C6118.0 (4)C5B'—C6'—C7'119.7 (5)
C9A—C5B—C5A106.5 (4)C5B'—C6'—H6'127 (3)
C6—C5B—C5A135.5 (4)C7'—C6'—H6'114 (3)
C7—C6—C5B118.1 (5)C6'—C7'—C8'120.4 (5)
C7—C6—H6125 (2)C6'—C7'—H7'126 (2)
C5B—C6—H6117 (2)C8'—C7'—H7'113 (2)
C6—C7—C8122.8 (5)C9—C8—C7121.1 (5)
C6—C7—H7118 (3)C9—C8—H8115 (3)
C8—C7—H7119 (3)C7—C8—H8124 (3)
C8—C9—C9A116.4 (5)C9'—C8'—C7'121.2 (5)
C8—C9—H9121 (3)C9'—C8'—H8'119 (2)
C9A—C9—H9122 (3)C7'—C8'—H8'120 (2)
C9—C9A—N10128.2 (4)C8'—C9'—C9A'118.5 (5)
C9—C9A—C5B123.7 (4)C8'—C9'—H9'124 (2)
N10—C9A—C5B108.1 (4)C9A'—C9'—H9'117 (2)
N10—C10A—C5A109.9 (4)N10'—C9A'—C9'131.0 (4)
N10—C10A—C10B123.7 (4)N10'—C9A'—C5B'107.8 (4)
C5A—C10A—C10B126.4 (4)C9'—C9A'—C5B'121.1 (4)
O1—C10B—C10A110.8 (4)N10'—C10—C5A'108.6 (4)
O1—C10B—C3A105.8 (4)N10'—C10—C10'124.0 (4)
C10A—C10B—C3A110.3 (4)C5A'—C10—C10'127.4 (4)
O1—C10B—H10B113 (3)O1'—C10'—C10111.3 (4)
C10A—C10B—H10B109 (3)O1'—C10'—C3A'105.5 (4)
C3A—C10B—H10B107 (3)C10—C10'—C3A'109.1 (4)
C10'—O1'—C2'109.8 (4)O1'—C10'—H10A112 (2)
C10—N10'—C9A'110.0 (4)C10—C10'—H10A105 (2)
C10—N10'—H10'123 (3)C3A'—C10'—H10A113 (2)
C10B—O1—C2—C38.7 (6)C10'—O1'—C2'—C3'0.3 (7)
C2—O1—C10B—C10A92.5 (4)C2'—O1'—C10'—C1096.0 (5)
C2—O1—C10B—C3A27.2 (5)C2'—O1'—C10'—C3A'22.3 (6)
C10A—N10—C9A—C9179.1 (4)C10—N10'—C9A'—C9'177.3 (4)
C10A—N10—C9A—C5B0.9 (5)C10—N10'—C9A'—C5B'1.3 (5)
C9A—N10—C10A—C5A1.0 (5)C3A'—C3'—C2'—O1'21.5 (7)
C9A—N10—C10A—C10B178.8 (4)C10'—C3A'—C4'—C5'39.9 (8)
C3A—C3—C2—O112.9 (7)C3'—C3A'—C4'—C5'78.2 (7)
C4—C3A—C3—C2152.8 (5)C10'—C3A'—C3'—C2'33.5 (6)
C10B—C3A—C3—C228.0 (6)C4'—C3A'—C3'—C2'159.1 (5)
C10B—C3A—C4—C542.7 (6)C3'—C3A'—C10'—O1'34.5 (4)
C3—C3A—C4—C574.9 (6)C4'—C3A'—C10'—O1'160.1 (4)
O2—C5—C4—C3A155.4 (4)C3'—C3A'—C10'—C1085.3 (4)
C5A—C5—C4—C3A24.1 (6)C4'—C3A'—C10'—C1040.4 (6)
C10A—C5A—C5—O2175.4 (4)O2'—C5'—C4'—C3A'161.7 (5)
C5B—C5A—C5—O22.1 (7)C5A'—C5'—C4'—C3A'17.8 (8)
C10A—C5A—C5—C44.1 (6)C10—C5A'—C5'—O2'179.9 (5)
C5B—C5A—C5—C4178.4 (4)C5B'—C5A'—C5'—O2'3.3 (8)
C10A—C5A—C5B—C9A0.2 (4)C10—C5A'—C5'—C4'0.6 (7)
C5—C5A—C5B—C9A177.6 (4)C5B'—C5A'—C5'—C4'176.2 (5)
C10A—C5A—C5B—C6179.2 (5)C5'—C5A'—C10—N10'178.1 (4)
C5—C5A—C5B—C63.0 (8)C5B'—C5A'—C10—N10'0.6 (5)
C5B—C5A—C10A—N100.7 (4)C5'—C5A'—C10—C10'3.5 (7)
C5—C5A—C10A—N10177.3 (4)C5B'—C5A'—C10—C10'179.1 (4)
C5B—C5A—C10A—C10B179.1 (4)C6'—C5B'—C5A'—C10179.1 (5)
C5—C5A—C10A—C10B2.8 (6)C9A'—C5B'—C5A'—C100.2 (5)
C9A—C5B—C6—C70.1 (6)C6'—C5B'—C5A'—C5'2.0 (8)
C5A—C5B—C6—C7179.3 (5)C9A'—C5B'—C5A'—C5'176.9 (4)
C5B—C6—C7—C80.5 (8)C9A'—C5B'—C6'—C7'0.2 (7)
C6—C7—C8—C90.7 (8)C5A'—C5B'—C6'—C7'178.6 (4)
C9A—C9—C8—C70.5 (7)C6'—C5B'—C9A'—N10'180.0 (4)
C9—C9A—C5B—C60.1 (6)C5A'—C5B'—C9A'—N10'0.9 (4)
N10—C9A—C5B—C6179.9 (4)C6'—C5B'—C9A'—C9'1.3 (6)
C9—C9A—C5B—C5A179.6 (4)C5A'—C5B'—C9A'—C9'177.9 (4)
N10—C9A—C5B—C5A0.4 (4)C8'—C7'—C6'—C5B'0.5 (7)
N10—C9A—C9—C8179.9 (4)C6'—C7'—C8'—C9'0.3 (7)
C5B—C9A—C9—C80.2 (7)C9A'—C9'—C8'—C7'0.7 (7)
N10—C10A—C10B—O142.9 (6)N10'—C9A'—C9'—C8'180.0 (4)
C5A—C10A—C10B—O1137.3 (4)C5B'—C9A'—C9'—C8'1.5 (7)
N10—C10A—C10B—C3A159.8 (4)N10'—C10—C10'—O1'41.6 (6)
C5A—C10A—C10B—C3A20.4 (6)C5A'—C10—C10'—O1'140.2 (4)
O1—C10B—C3A—C4158.5 (4)N10'—C10—C10'—C3A'157.7 (4)
C10A—C10B—C3A—C438.6 (6)C5A'—C10—C10'—C3A'24.1 (6)
O1—C10B—C3A—C333.8 (5)C9A'—N10'—C10—C5A'1.2 (5)
C10A—C10B—C3A—C386.1 (5)C9A'—N10'—C10—C10'179.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10···O2i0.96 (5)1.98 (6)2.876 (6)155 (4)
N10—H10···O1ii0.83 (5)2.01 (5)2.829 (5)169 (4)
Symmetry codes: (i) x, y1, z1; (ii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC14H13NO2
Mr227.26
Crystal system, space groupTriclinic, 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)
V3)1119.21 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerEnraf–Nonius TurboCAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.961, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
4127, 3933, 1657
Rint0.032
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.169, 0.96
No. of reflections3933
No. of parameters411
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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—C38.7 (6)C10'—O1'—C2'—C3'0.3 (7)
C2—O1—C10B—C3A27.2 (5)C2'—O1'—C10'—C3A'22.3 (6)
C3A—C3—C2—O112.9 (7)C3A'—C3'—C2'—O1'21.5 (7)
C10B—C3A—C3—C228.0 (6)C10'—C3A'—C4'—C5'39.9 (8)
C10B—C3A—C4—C542.7 (6)C10'—C3A'—C3'—C2'33.5 (6)
C5A—C5—C4—C3A24.1 (6)C3'—C3A'—C10'—O1'34.5 (4)
C10A—C5A—C5—C44.1 (6)C4'—C3A'—C10'—C1040.4 (6)
C5—C5A—C10A—C10B2.8 (6)C5A'—C5'—C4'—C3A'17.8 (8)
C5A—C10A—C10B—C3A20.4 (6)C10—C5A'—C5'—C4'0.6 (7)
C10A—C10B—C3A—C438.6 (6)C5'—C5A'—C10—N10'178.1 (4)
O1—C10B—C3A—C333.8 (5)C5A'—C10—C10'—C3A'24.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10···O2i0.96 (5)1.98 (6)2.876 (6)155 (4)
N10'—H10'···O1ii0.83 (5)2.01 (5)2.829 (5)169 (4)
Symmetry codes: (i) x, y1, z1; (ii) x+1, y+1, z+2.
 

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