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The title compound, C18H22N2O3, consists of a tetra­cyclic ring system containing an azocino skeleton with a dimethoxy­ethyl group as a substituent. The benzene and five-membered rings are nearly coplanar, with a dihedral angle of 1.26 (8)°. In the crystal structure, inter­molecular N—H...O hydrogen bonds link the mol­ecules into chains parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029480/rk2017sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029480/rk2017Isup2.hkl
Contains datablock I

CCDC reference: 655002

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.067
  • wR factor = 0.231
  • Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C5 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The hexahydro-1,5-methano-azocino[4,3-b]indole core structure can be considered to be synthetic precursor for most of the pentacyclic and tetracyclic indol alkaloids of biological interests (Hesse, 2002; Bosch & Bonjoch, 1988; Saxton, 1983), such as akuminicine and uleine. Most of them have the pentacyclic ring system as a common structural element and include a large group of naturally occurring compounds such as strychnine, a covulsant poison.

The structures of tricyclic, tetracyclic and pentacyclic ring systems with different substituent of azocino[4,3-b]indole core, have been the subject of much interest in our laboratory. These include 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, (II) (Hökelek et al., 2004), 12-ethyl-2-methyl- 6,6-ethylenedithio-1,2,3,4,5,6-hexahydro-1,5-methano-2-azocino[4,3-b]indole- 3-one, (III), (Uludağ et al., 2006) and 4-ethyl-6,6-ethylenedithio-2-(2- methoxymethyl)-7-methoxymethylene-2,3,4,5,6,7-hexahydro-1,5-methano-1H- azocino[4,3-b]indol-3-one, (IV), (Hökelek et al., 2006). The present study was undertaken to ascertain the crystal structure of the title compound, (I).

The molecule of the title compound, (I), (Fig. 1), consists of a tetracyclic system containing an azocino skeleton with dimethoxyethyl group as substituent at position N2, in which the bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds N7—C6a [1.377 (3) Å] and N7—C7a [1.376 (3) Å] agree well with those in compounds (II) [1.392 (8) and 1.370 (8) Å] and (IV) [1.393 (4) and 1.386 (5) Å]. In all three structures atom N7 is substituted. The absolute configurations of C1 and C5 are R and S (Fig. 1), respectively.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C7a/C8/C9/C10/C11/C11a) and B (N7/C7a/C11a/C11b/C6a) are planar. They are also nearly co-planar with a dihedral angle of A/B = 1.25 (7)°. Rings C (C1/C11b/C6a/C6/C5/C12) and D (C1/N2/C3/C4/C5/C12) are, of course, not planar. Atom C12 deviates from the planes of E (C1/C5/C6/C6a/C11b) and F (C1/N2/C3/C4/C5) by -0.710 (2) Å and 0.7445 (2) Å, respectively, where the dihedral angle between the planes of E and F is E/F = 69.72 (6)°. On the other hand, the dihedral angles between the plane of G (C1/C5/C12) and planes of E and F are 53.93 (7)° and 69.84 (6)°, respectively.

In the crystal structure, intermolecular N–H···O hydrogen bonds (see Table) link the molecules into chains nearly parallel to b axis (Fig. 2), in which they may be effective in the stabilization of the structure; van der Waals interactions are also effective in the molecular packing.

Related literature top

For general backgroud, see: Hesse (2002); Bosch & Bonjoch (1988); Saxton (1983); Allen et al. (1987). For related literature, see: Hökelek et al. (2004, 2006); Uludağ et al. (2006).

Experimental top

The title compound, (I), was prepared from N-(2',2'-Dimethoxyethyl)-6- (1,2-dithiolane-2-yl)-1,2,3,4,5,6-hexahydro-1,5-methano-3-oxo-1H- azocino[4,3-b]indole (1.0 g, 2.47 mmol) and Raney nickel (1.0 g) in ethanol (50 ml). The mixture was refluxed for 22 h, and then filtered and evaporated. The residue was purified by silica gel chromatography using ethyl acetate and crystallized from diethyl ether (yield; 0.42 g, 54%, m.p. 453 K).

Structure description top

The hexahydro-1,5-methano-azocino[4,3-b]indole core structure can be considered to be synthetic precursor for most of the pentacyclic and tetracyclic indol alkaloids of biological interests (Hesse, 2002; Bosch & Bonjoch, 1988; Saxton, 1983), such as akuminicine and uleine. Most of them have the pentacyclic ring system as a common structural element and include a large group of naturally occurring compounds such as strychnine, a covulsant poison.

The structures of tricyclic, tetracyclic and pentacyclic ring systems with different substituent of azocino[4,3-b]indole core, have been the subject of much interest in our laboratory. These include 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, (II) (Hökelek et al., 2004), 12-ethyl-2-methyl- 6,6-ethylenedithio-1,2,3,4,5,6-hexahydro-1,5-methano-2-azocino[4,3-b]indole- 3-one, (III), (Uludağ et al., 2006) and 4-ethyl-6,6-ethylenedithio-2-(2- methoxymethyl)-7-methoxymethylene-2,3,4,5,6,7-hexahydro-1,5-methano-1H- azocino[4,3-b]indol-3-one, (IV), (Hökelek et al., 2006). The present study was undertaken to ascertain the crystal structure of the title compound, (I).

The molecule of the title compound, (I), (Fig. 1), consists of a tetracyclic system containing an azocino skeleton with dimethoxyethyl group as substituent at position N2, in which the bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds N7—C6a [1.377 (3) Å] and N7—C7a [1.376 (3) Å] agree well with those in compounds (II) [1.392 (8) and 1.370 (8) Å] and (IV) [1.393 (4) and 1.386 (5) Å]. In all three structures atom N7 is substituted. The absolute configurations of C1 and C5 are R and S (Fig. 1), respectively.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C7a/C8/C9/C10/C11/C11a) and B (N7/C7a/C11a/C11b/C6a) are planar. They are also nearly co-planar with a dihedral angle of A/B = 1.25 (7)°. Rings C (C1/C11b/C6a/C6/C5/C12) and D (C1/N2/C3/C4/C5/C12) are, of course, not planar. Atom C12 deviates from the planes of E (C1/C5/C6/C6a/C11b) and F (C1/N2/C3/C4/C5) by -0.710 (2) Å and 0.7445 (2) Å, respectively, where the dihedral angle between the planes of E and F is E/F = 69.72 (6)°. On the other hand, the dihedral angles between the plane of G (C1/C5/C12) and planes of E and F are 53.93 (7)° and 69.84 (6)°, respectively.

In the crystal structure, intermolecular N–H···O hydrogen bonds (see Table) link the molecules into chains nearly parallel to b axis (Fig. 2), in which they may be effective in the stabilization of the structure; van der Waals interactions are also effective in the molecular packing.

For general backgroud, see: Hesse (2002); Bosch & Bonjoch (1988); Saxton (1983); Allen et al. (1987). For related literature, see: Hökelek et al. (2004, 2006); Uludağ et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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 structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 20% probability level. The hydrogen atoms are drawn as spheres with arbitrary radius.
[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: (') 1/2 - x, 1/2 + y, 1/2 - z].
2-(2,2-Dimethoxyethyl)-3-oxo-1,2,3,4,5,6-hexahydro-1,5-methano- 7H-azocino[4,3-b]indole top
Crystal data top
C18H22N2O3F(000) = 672
Mr = 314.38Dx = 1.259 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6164 reflections
a = 10.0347 (4) Åθ = 2.1–30.6°
b = 8.4616 (7) ŵ = 0.09 mm1
c = 20.1168 (9) ÅT = 294 K
β = 103.750 (3)°Prism, colorless
V = 1659.16 (17) Å30.35 × 0.20 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
5094 independent reflections
Radiation source: fine-focus sealed tube2625 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
ω scansθmax = 30.7°, θmin = 2.1°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1414
Tmin = 0.971, Tmax = 0.987k = 1012
47331 measured reflectionsl = 2828
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1052P)2 + 0.0611P]
where P = (Fo2 + 2Fc2)/3
5094 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C18H22N2O3V = 1659.16 (17) Å3
Mr = 314.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0347 (4) ŵ = 0.09 mm1
b = 8.4616 (7) ÅT = 294 K
c = 20.1168 (9) Å0.35 × 0.20 × 0.15 mm
β = 103.750 (3)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
5094 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
2625 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.987Rint = 0.076
47331 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.231H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.32 e Å3
5094 reflectionsΔρmin = 0.32 e Å3
214 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
O10.05988 (15)0.19313 (18)0.09564 (7)0.0701 (4)
O20.31895 (16)0.1229 (2)0.14450 (8)0.0794 (5)
O30.2405 (2)0.12092 (19)0.12128 (10)0.0944 (6)
C10.0680 (2)0.3424 (2)0.23627 (10)0.0594 (5)
H10.14760.30340.25160.071*
N20.04095 (17)0.2356 (2)0.18262 (8)0.0595 (4)
C30.03154 (19)0.2844 (2)0.13862 (10)0.0581 (5)
C40.0769 (2)0.4547 (3)0.14005 (12)0.0715 (6)
H4A0.04770.49550.09380.086*
H4B0.17640.45560.15190.086*
C50.0288 (2)0.5715 (3)0.18762 (11)0.0702 (6)
H50.00530.67120.16290.084*
C60.1378 (3)0.6059 (3)0.25340 (12)0.0768 (6)
H6A0.22620.62130.24270.092*
H6B0.11440.70190.27430.092*
C6A0.1460 (2)0.4708 (2)0.30211 (10)0.0626 (5)
C7A0.2202 (2)0.3180 (2)0.39445 (10)0.0590 (5)
N70.24803 (18)0.4512 (2)0.36095 (9)0.0663 (5)
H70.315 (2)0.529 (3)0.3798 (12)0.077 (7)*
C80.2921 (2)0.2521 (3)0.45622 (10)0.0677 (6)
H80.37290.29740.48130.081*
C90.2393 (3)0.1185 (3)0.47851 (11)0.0756 (6)
H90.28480.07240.51960.091*
C100.1190 (3)0.0506 (3)0.44087 (12)0.0792 (7)
H100.08560.04010.45740.095*
C110.0475 (2)0.1142 (3)0.37944 (11)0.0673 (6)
H110.03280.06690.35490.081*
C11A0.0979 (2)0.2506 (2)0.35487 (9)0.0560 (5)
C11B0.0528 (2)0.3514 (2)0.29624 (10)0.0570 (5)
C120.1000 (2)0.5072 (3)0.20518 (12)0.0705 (6)
H12A0.17390.50110.16420.085*
H12B0.12850.57650.23760.085*
C130.0850 (2)0.0703 (2)0.18074 (10)0.0644 (5)
H13A0.10200.04200.22470.077*
H13B0.01210.00300.17280.077*
C140.2129 (2)0.0419 (2)0.12555 (11)0.0636 (5)
H140.20090.08150.08160.076*
C150.4422 (3)0.1293 (4)0.09197 (15)0.0976 (9)
H15A0.42300.17340.05130.146*
H15B0.50810.19430.10670.146*
H15C0.47840.02450.08250.146*
C160.2419 (5)0.1910 (4)0.05865 (17)0.1358 (15)
H16A0.30860.13930.02320.204*
H16B0.26510.30080.06020.204*
H16C0.15280.18140.04930.204*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0713 (9)0.0756 (10)0.0610 (9)0.0142 (7)0.0112 (7)0.0032 (7)
O20.0630 (9)0.0999 (12)0.0721 (10)0.0028 (8)0.0097 (8)0.0025 (8)
O30.1162 (15)0.0666 (10)0.0902 (12)0.0259 (9)0.0043 (11)0.0006 (9)
C10.0540 (10)0.0674 (12)0.0553 (11)0.0031 (9)0.0100 (8)0.0005 (9)
N20.0593 (9)0.0623 (10)0.0542 (9)0.0065 (7)0.0080 (7)0.0011 (7)
C30.0506 (10)0.0666 (12)0.0526 (10)0.0055 (9)0.0037 (8)0.0049 (9)
C40.0750 (14)0.0717 (14)0.0679 (13)0.0088 (11)0.0176 (11)0.0050 (11)
C50.0802 (14)0.0586 (12)0.0681 (13)0.0022 (10)0.0104 (11)0.0093 (10)
C60.0919 (16)0.0639 (13)0.0710 (14)0.0125 (12)0.0122 (12)0.0034 (11)
C6A0.0646 (12)0.0637 (12)0.0573 (11)0.0051 (9)0.0101 (9)0.0005 (9)
C7A0.0596 (11)0.0642 (12)0.0527 (10)0.0001 (9)0.0122 (9)0.0055 (8)
N70.0625 (10)0.0699 (11)0.0622 (10)0.0150 (9)0.0064 (8)0.0034 (8)
C80.0651 (12)0.0834 (15)0.0506 (10)0.0062 (11)0.0059 (9)0.0073 (10)
C90.0920 (17)0.0815 (15)0.0501 (11)0.0105 (13)0.0105 (11)0.0059 (10)
C100.1020 (18)0.0760 (15)0.0607 (13)0.0012 (13)0.0218 (13)0.0082 (11)
C110.0739 (13)0.0700 (13)0.0579 (12)0.0117 (10)0.0158 (10)0.0005 (9)
C11A0.0568 (11)0.0605 (11)0.0509 (10)0.0019 (8)0.0132 (8)0.0023 (8)
C11B0.0549 (10)0.0619 (11)0.0534 (10)0.0039 (9)0.0115 (8)0.0005 (8)
C120.0682 (13)0.0753 (14)0.0652 (12)0.0135 (11)0.0101 (10)0.0026 (10)
C130.0670 (12)0.0633 (12)0.0574 (11)0.0056 (10)0.0037 (9)0.0057 (9)
C140.0692 (12)0.0615 (12)0.0564 (11)0.0103 (10)0.0074 (9)0.0035 (9)
C150.0691 (15)0.119 (2)0.096 (2)0.0027 (14)0.0021 (14)0.0302 (16)
C160.190 (4)0.087 (2)0.098 (2)0.014 (2)0.030 (2)0.0281 (18)
Geometric parameters (Å, º) top
O1—C31.242 (2)C6A—C61.495 (3)
O2—C141.393 (3)C7A—C81.396 (3)
O2—C151.424 (3)C7A—C11A1.414 (3)
O3—C141.404 (2)C8—C91.368 (3)
O3—C161.390 (4)C8—H80.9300
N2—C31.338 (3)C9—C101.388 (3)
N2—C131.464 (3)C9—H90.9300
N2—C11.482 (2)C10—H100.9300
N7—C7A1.376 (3)C11—C101.382 (3)
N7—C6A1.378 (2)C11—H110.9300
N7—H70.95 (2)C11A—C111.397 (3)
C1—C11B1.495 (3)C11A—C11B1.439 (3)
C1—C121.530 (3)C12—H12A0.9700
C1—H10.9800C12—H12B0.9700
C3—C41.509 (3)C13—C141.503 (3)
C4—H4A0.9700C13—H13A0.9700
C4—H4B0.9700C13—H13B0.9700
C5—C41.532 (3)C14—H140.9800
C5—H50.9800C15—H15A0.9600
C5—C61.531 (3)C15—H15B0.9600
C5—C121.519 (3)C15—H15C0.9600
C6—H6A0.9700C16—H16A0.9600
C6—H6B0.9700C16—H16B0.9600
C6A—C11B1.362 (3)C16—H16C0.9600
C14—O2—C15113.62 (19)C9—C8—H8121.2
C16—O3—C14115.7 (2)C7A—C8—H8121.2
C3—N2—C13119.09 (18)C8—C9—C10121.2 (2)
C3—N2—C1121.07 (16)C8—C9—H9119.4
C13—N2—C1119.67 (16)C10—C9—H9119.4
C7A—N7—C6A108.88 (17)C11—C10—C9121.7 (2)
C7A—N7—H7125.2 (14)C11—C10—H10119.1
C6A—N7—H7124.6 (14)C9—C10—H10119.1
N7—C7A—C8129.9 (2)C10—C11—C11A118.9 (2)
N7—C7A—C11A107.72 (17)C10—C11—H11120.5
C8—C7A—C11A122.4 (2)C11A—C11—H11120.5
C11—C11A—C7A118.18 (19)C6A—C11B—C11A107.04 (17)
C11—C11A—C11B135.28 (19)C6A—C11B—C1121.07 (17)
C7A—C11A—C11B106.52 (17)C11A—C11B—C1131.89 (17)
N2—C1—C11B111.41 (16)C5—C12—C1108.28 (17)
N2—C1—C12108.36 (16)C5—C12—H12A110.0
C11B—C1—C12109.54 (17)C1—C12—H12A110.0
N2—C1—H1109.2C5—C12—H12B110.0
C11B—C1—H1109.2C1—C12—H12B110.0
C12—C1—H1109.2H12A—C12—H12B108.4
O1—C3—N2121.26 (19)N2—C13—C14111.79 (16)
O1—C3—C4119.29 (18)N2—C13—H13A109.3
N2—C3—C4119.43 (18)C14—C13—H13A109.3
C3—C4—C5119.29 (18)N2—C13—H13B109.3
C3—C4—H4A107.5C14—C13—H13B109.3
C5—C4—H4A107.5H13A—C13—H13B107.9
C3—C4—H4B107.5O2—C14—O3110.32 (18)
C5—C4—H4B107.5O2—C14—C13107.03 (17)
H4A—C4—H4B107.0O3—C14—C13108.87 (17)
C12—C5—C6109.86 (19)O2—C14—H14110.2
C12—C5—C4109.05 (18)O3—C14—H14110.2
C6—C5—C4113.3 (2)C13—C14—H14110.2
C12—C5—H5108.2O2—C15—H15A109.5
C6—C5—H5108.2O2—C15—H15B109.5
C4—C5—H5108.2H15A—C15—H15B109.5
C6A—C6—C5109.75 (18)O2—C15—H15C109.5
C6A—C6—H6A109.7H15A—C15—H15C109.5
C5—C6—H6A109.7H15B—C15—H15C109.5
C6A—C6—H6B109.7O3—C16—H16A109.5
C5—C6—H6B109.7O3—C16—H16B109.5
H6A—C6—H6B108.2H16A—C16—H16B109.5
C11B—C6A—N7109.84 (18)O3—C16—H16C109.5
C11B—C6A—C6125.46 (19)H16A—C16—H16C109.5
N7—C6A—C6124.68 (19)H16B—C16—H16C109.5
C9—C8—C7A117.6 (2)
C15—O2—C14—O371.6 (2)C12—C5—C6—C6A45.2 (3)
C15—O2—C14—C13170.10 (19)C4—C5—C6—C6A77.0 (2)
C16—O3—C14—O2123.3 (3)C6—C5—C12—C168.7 (2)
C16—O3—C14—C13119.5 (3)C4—C5—C12—C156.0 (2)
C13—N2—C3—O11.3 (3)C11B—C6A—C6—C513.1 (3)
C1—N2—C3—O1176.60 (17)N7—C6A—C6—C5168.7 (2)
C13—N2—C3—C4179.79 (17)N7—C6A—C11B—C11A0.3 (2)
C1—N2—C3—C44.9 (3)C6—C6A—C11B—C11A178.1 (2)
C3—N2—C1—C11B80.3 (2)N7—C6A—C11B—C1179.11 (18)
C13—N2—C1—C11B95.02 (19)C6—C6A—C11B—C12.5 (3)
C3—N2—C1—C1240.3 (2)N7—C7A—C8—C9178.9 (2)
C13—N2—C1—C12144.41 (18)C11A—C7A—C8—C90.7 (3)
C3—N2—C13—C1481.7 (2)N7—C7A—C11A—C11179.01 (18)
C1—N2—C13—C14102.9 (2)C8—C7A—C11A—C110.7 (3)
C6A—N7—C7A—C8178.8 (2)N7—C7A—C11A—C11B0.7 (2)
C6A—N7—C7A—C11A0.8 (2)C8—C7A—C11A—C11B179.03 (18)
C7A—N7—C6A—C11B0.7 (2)C7A—C8—C9—C100.3 (3)
C7A—N7—C6A—C6177.7 (2)C8—C9—C10—C110.1 (4)
N2—C1—C11B—C6A96.2 (2)C11A—C11—C10—C90.2 (3)
C12—C1—C11B—C6A23.7 (3)C7A—C11A—C11—C100.2 (3)
N2—C1—C11B—C11A83.0 (3)C11B—C11A—C11—C10178.0 (2)
C12—C1—C11B—C11A157.1 (2)C11—C11A—C11B—C6A178.2 (2)
N2—C1—C12—C566.2 (2)C7A—C11A—C11B—C6A0.2 (2)
C11B—C1—C12—C555.5 (2)C11—C11A—C11B—C12.5 (4)
O1—C3—C4—C5173.37 (19)C7A—C11A—C11B—C1179.5 (2)
N2—C3—C4—C55.2 (3)N2—C13—C14—O267.5 (2)
C12—C5—C4—C321.6 (3)N2—C13—C14—O3173.28 (18)
C6—C5—C4—C3101.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O1i0.95 (2)1.86 (2)2.805 (2)172 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H22N2O3
Mr314.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)10.0347 (4), 8.4616 (7), 20.1168 (9)
β (°) 103.750 (3)
V3)1659.16 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.20 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID-S
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.971, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
47331, 5094, 2625
Rint0.076
(sin θ/λ)max1)0.717
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.231, 1.06
No. of reflections5094
No. of parameters214
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.32

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O1i0.95 (2)1.86 (2)2.805 (2)172 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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