Download citation
Download citation
link to html
The bond distances in the mol­ecule of the title compound, C19H14N2O4, provide evidence for electronic polarization in the amino­aryl­propenone fragment and for bond fixation in the quinolinone unit. Mol­ecules are linked by N-H...O and C-H...O hydrogen bonds into chains in which centrosymmetric rings of R22(8) and R22(18) types alternate, and these chains are linked into sheets by a single aromatic [pi]-[pi] stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109053554/sk3356sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109053554/sk3356Isup2.hkl
Contains datablock I

CCDC reference: 765481

Comment top

We report here the molecular and supramolecular structure of the title compound, (I) (Fig. 1). Dioxolotetrahydroquinolin-8-one units are found in a number of compounds used as antimitotic and antitumour agents (Prager & Thredgold, 1968; Donnelly & Farell, 1990; Kurasawa et al., 2002; Zhang et al., 2000), and 2-aminochalcones are useful intermediates for the synthesis of such quinolinone derivatives. Several years ago we reported the molecular and supramolecular structures of a number of such 2-aminochalcones (Low, Cobo, Nogueras et al., 2004), compounds (II)–(VI) (see scheme), and of some quinolinones formed by their acid-catalysed cyclization (Low, Cobo, Cuervo et al., 2004). Compound (I), in which the terminal substituted aryl group present in compounds (II)–(VI) has been replaced by a 2-oxoquinolin-3-yl unit, was prepared by a base-catalysed condensation between an acetophenone and an aldehyde, for use as an intermediate in the synthesis of the corresponding dihydroquinolin-8-one by 6-endo intramolecular cyclization (Low, Cobo, Cuervo et al., 2004; Abonía et al., 2008).

Compound (I) crystallizes with Z' = 1, as do (II), (VI) and the monoclinic polymorph of (III) (Low, Cobo, Nogueras et al., 2004). On the other hand, the triclinic polymorph of (III), and (IV) and (V), all crystallize with Z' = 2. No simple explanation of this behaviour presents itself. Within the molecule of (I), the spacer unit joining the two ring systems adopts an effectively planar all-trans configuration, and the two adjacent rings are almost coplanar with the spacer unit, as shown by the key torsion angles (Table 1). This planarity permits, but not does require, extensive electronic delocalization. The sole exception to the skeletal planarity is found in the dioxolane ring, where atom C12 is modestly displaced by 0.057 (2) Å from the mean plane of this ring, corresponding to an envelope fold across the line O11···O13.

In the aryl ring C13a/C14–C17/C17a, the C13a—C14 and C17—C17a bonds are both significantly shorter than the other four C—C distances in this ring (Table 1). At the same time, the C1—O1 bond is long for its type [mean value (Allen et al., 1987) 1.222 Å] and the C1—C15 bond is short for its type (mean value 1.488 Å). The C15—C16 bond is one of the longer ones in this aryl ring, and the C16—N16 bond is also short for its type (mean value 1.394 Å, lower quartile value 1.385 Å). Similar patterns of distances were observed in the corresponding molecular fragments in compounds (II)-(VI) (Low, Cobo, Nogueras et al., 2004). The C—C distances in the quinoline portion of the molecule provide evidence for bond fixation, as the C35—C36 and C37—C38 bonds are shorter than the other bonds in this carbocyclic ring. These observations, taken as a whole, indicate that the form (Ia) is a significant contributor to the overall electronic structure, in addition to form (I), although there appears to be no electronic delocalization between the two ring systems despite the planarity of the molecular skeleton.

There is an intramolecular hydrogen bond (Table 2) forming an S(6) motif (Bernstein et al., 1995), which may be regarded as charge-assisted (Gilli et al., 1994), but the second N—H bond of the amino group plays no role in the intermolecular hydrogen bonding, as there is no potential acceptor within plausible hydrogen-bonding distance. Instead, the molecules are linked by one N—H···O hydrogen bond, using the quinolinone N—H bond, and one C—H···O hydrogen bond, both almost linear (Table 2), into a chain containing two types of centrosymmetric ring. Rings of R22(8) type built from paired N—H···O hydrogen bonds are centred at (2n - 1/2, -n + 1/2, 1/2), where n represents an integer, and these alternate with R22(18) rings built from paired C—H···O hydrogen bonds and centred at (2n + 1/2, -n, 1/2), where n again represents an integer, so forming a chain running parallel to the [210] direction (Fig. 2).

A single aromatic ππ stacking interaction links, albeit fairly weakly, the hydrogen-bonded chains into a sheet. The rings C13a/C14–C17/C17a in the molecules at (x, y, z) and (1 - x, - y, 1 - z) are strictly parallel, with an interplanar spacing of 3.641 (2) Å. The ring centroid separation is 3.812 (2) Å, corresponding to a ring-centroid offset of 1.131 (2) Å. The effect of this interaction, when propagated by inversion, is to link the chains parallel to [210] into a sheet parallel to (122) (Fig. 2), but there are no direction-specific interactions between adjacent sheets. In this context, it is interesting to note that not only does the amino group play no role in the intermolecular aggregation, but neither do atoms O11 and O13.

The formation of sheets generated by the π-stacking of hydrogen-bonded chains was also observed in (IV) and (VI) (Low, Cobo, Nogueras et al., 2004), although in each of these structures the chains are simple chains of C(7) and C(10) types, as opposed to the chains of rings observed here in (I). In both (II) and the monoclinic polymorph of (III), a combination of N—H···O and C—H···π(arene) hydrogen bonds forms the sheet structures directly, without any ππ stacking. By contrast, in the triclinic polymorph of (III), the structure is built from simple C(8) chains without any ππ stacking, while in (V) the molecules are linked by N—H···O hydrogen bonds into centrosymmetric tetramers. Thus within this series of compounds, (I)–(VI), the hydrogen-bonding can give rise to aggregation in zero, one or two dimensions. This variation, combined with the differing Z' values, points to considerable structural diversity within this series of rather closely related compounds.

Experimental top

A mixture of 1-(6-aminobenzo[1,3]dioxol-5-yl)ethanone (0.50 g, 2.8 mmol) and 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (0.48 g, 2.8 mmol) in ethanol (10 ml) containing 20% (w/v) aqueous sodium hydroxide solution (0.5 ml) was heated under reflux for 10 min. The mixture was cooled to ambient temperature, and the resulting solid precipitate was collected by filtration, washed successively with ethanol (3 ml) and water (3 ml), and then dried under reduced pressure to give the title compound, (I), in 55% yield. Dark-red crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of a solution of (I) in dimethylformamide (m.p. 524 K). EIMS (70 eV), m/z (%) 334 (12 [M+]), 333 (62 [M - 1]), 190 (23, [M - C9H6N]. Analysis, found: C 68.3, H 4.1, N 8.3%; C19H14N2O4 requires: C 68.3, H 4.2 N 8.4%.

Refinement top

All H atoms were located in difference maps. The coordinates of the H atoms bonded to N16 were refined without restraint, with Uiso(H) = 1.2Ueq(N), giving N—H distances of 0.89 (2) and 0.91 (2) Å, and a sum of bond angles at N16 of ca 349°. The remaining H atoms were treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (aromatic or alkenyl) or 0.99 Å (CH2) and N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(carrier).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and the intramolecular hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing the π-stacking of hydrogen-bonded chains along [210] to form a sheet parallel to (122). For the sake of clarity, H atoms bonded to C atoms which are not involved in the motifs shown have been omitted.
1-(6-Amino-1,3-benzodioxol-5-yl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)prop-2- enone top
Crystal data top
C19H14N2O4Z = 2
Mr = 334.32F(000) = 348
Triclinic, P1Dx = 1.525 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7799 (2) ÅCell parameters from 2858 reflections
b = 9.9485 (3) Åθ = 3.1–26.1°
c = 13.0849 (5) ŵ = 0.11 mm1
α = 83.343 (2)°T = 120 K
β = 86.652 (2)°Block, red
γ = 77.128 (2)°0.10 × 0.06 × 0.06 mm
V = 728.13 (4) Å3
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
2858 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2377 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 9.091 pixels mm-1θmax = 26.1°, θmin = 3.1°
ϕ and ω scansh = 76
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1211
Tmin = 0.989, Tmax = 0.994l = 1616
9539 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.047P)2 + 0.3719P]
where P = (Fo2 + 2Fc2)/3
2858 reflections(Δ/σ)max = 0.001
232 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C19H14N2O4γ = 77.128 (2)°
Mr = 334.32V = 728.13 (4) Å3
Triclinic, P1Z = 2
a = 5.7799 (2) ÅMo Kα radiation
b = 9.9485 (3) ŵ = 0.11 mm1
c = 13.0849 (5) ÅT = 120 K
α = 83.343 (2)°0.10 × 0.06 × 0.06 mm
β = 86.652 (2)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
2858 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2377 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.994Rint = 0.033
9539 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å3
2858 reflectionsΔρmin = 0.24 e Å3
232 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4679 (3)0.35681 (16)0.28016 (12)0.0202 (3)
O10.6323 (2)0.25307 (11)0.29335 (9)0.0263 (3)
C20.2513 (3)0.36683 (16)0.34788 (12)0.0201 (3)
H20.12770.44790.34110.024*
C30.2306 (3)0.26117 (16)0.41869 (12)0.0204 (3)
H30.36120.18370.42200.024*
O110.5005 (2)0.80979 (12)0.01246 (9)0.0296 (3)
C120.2516 (3)0.87584 (17)0.01063 (13)0.0284 (4)
H12A0.23060.97420.00190.034*
H12B0.18240.87260.07750.034*
O130.1356 (2)0.80294 (11)0.07047 (9)0.0278 (3)
C13a0.3034 (3)0.68551 (16)0.10278 (12)0.0206 (3)
C140.2805 (3)0.58113 (16)0.17678 (12)0.0198 (3)
H140.13310.58150.21300.024*
C150.4821 (3)0.47068 (15)0.19914 (11)0.0188 (3)
C160.7002 (3)0.47498 (16)0.14383 (12)0.0200 (3)
C170.7196 (3)0.59005 (16)0.07181 (12)0.0220 (4)
H170.86710.59700.03790.026*
C17a0.5198 (3)0.69051 (16)0.05271 (12)0.0212 (3)
N160.8976 (3)0.36867 (15)0.15665 (11)0.0239 (3)
H16A1.038 (4)0.3888 (19)0.1399 (14)0.029*
H16B0.887 (3)0.307 (2)0.2128 (15)0.029*
N310.3581 (2)0.33571 (13)0.56186 (10)0.0199 (3)
H310.48890.40080.56350.024*
C320.1853 (3)0.35897 (15)0.49073 (11)0.0192 (3)
O320.21982 (19)0.46824 (11)0.43087 (8)0.0228 (3)
C330.0333 (3)0.25025 (16)0.49099 (11)0.0189 (3)
C340.0485 (3)0.13472 (16)0.56019 (12)0.0201 (3)
H340.18950.06420.55970.024*
C34a0.1377 (3)0.11534 (16)0.63298 (12)0.0194 (3)
C350.1241 (3)0.00296 (16)0.70490 (12)0.0237 (4)
H350.01710.07360.70790.028*
C360.3125 (3)0.01683 (16)0.77048 (12)0.0259 (4)
H360.30250.09730.81820.031*
C370.5210 (3)0.08794 (17)0.76722 (12)0.0244 (4)
H370.65170.07740.81260.029*
C380.5377 (3)0.20550 (16)0.69906 (12)0.0217 (3)
H380.67820.27660.69790.026*
C38a0.3461 (3)0.21947 (15)0.63141 (11)0.0187 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0210 (8)0.0194 (8)0.0201 (8)0.0045 (6)0.0002 (6)0.0022 (6)
O10.0224 (6)0.0210 (6)0.0312 (6)0.0007 (5)0.0039 (5)0.0046 (5)
C20.0200 (8)0.0194 (8)0.0200 (8)0.0030 (6)0.0005 (6)0.0009 (6)
C30.0196 (8)0.0191 (8)0.0210 (8)0.0013 (6)0.0009 (6)0.0017 (6)
O110.0299 (6)0.0267 (6)0.0280 (6)0.0048 (5)0.0036 (5)0.0097 (5)
C120.0297 (9)0.0248 (9)0.0282 (9)0.0058 (7)0.0008 (7)0.0069 (7)
O130.0257 (6)0.0222 (6)0.0310 (7)0.0015 (5)0.0005 (5)0.0086 (5)
C13a0.0211 (8)0.0192 (8)0.0206 (8)0.0027 (6)0.0031 (6)0.0008 (6)
C140.0195 (8)0.0208 (8)0.0195 (8)0.0062 (6)0.0011 (6)0.0014 (6)
C150.0204 (8)0.0185 (8)0.0181 (8)0.0060 (6)0.0003 (6)0.0017 (6)
C160.0206 (8)0.0222 (8)0.0174 (8)0.0046 (6)0.0003 (6)0.0034 (6)
C170.0226 (8)0.0261 (8)0.0176 (8)0.0076 (7)0.0035 (6)0.0009 (6)
C17a0.0274 (8)0.0208 (8)0.0161 (7)0.0090 (7)0.0011 (6)0.0016 (6)
N160.0188 (7)0.0248 (7)0.0257 (7)0.0035 (6)0.0040 (6)0.0027 (6)
N310.0189 (7)0.0180 (7)0.0202 (7)0.0010 (5)0.0022 (5)0.0014 (5)
C320.0216 (8)0.0188 (7)0.0167 (7)0.0040 (6)0.0016 (6)0.0001 (6)
O320.0231 (6)0.0187 (6)0.0225 (6)0.0003 (5)0.0027 (5)0.0045 (4)
C330.0207 (8)0.0186 (7)0.0174 (7)0.0042 (6)0.0007 (6)0.0018 (6)
C340.0205 (8)0.0179 (7)0.0204 (8)0.0008 (6)0.0021 (6)0.0021 (6)
C34a0.0232 (8)0.0176 (7)0.0175 (7)0.0041 (6)0.0013 (6)0.0026 (6)
C350.0282 (9)0.0189 (8)0.0220 (8)0.0023 (7)0.0002 (7)0.0009 (6)
C360.0363 (10)0.0199 (8)0.0212 (8)0.0086 (7)0.0012 (7)0.0030 (6)
C370.0283 (9)0.0261 (8)0.0207 (8)0.0114 (7)0.0053 (7)0.0026 (6)
C380.0218 (8)0.0232 (8)0.0201 (8)0.0051 (7)0.0013 (6)0.0025 (6)
C38a0.0235 (8)0.0176 (7)0.0158 (7)0.0065 (6)0.0015 (6)0.0014 (6)
Geometric parameters (Å, º) top
O11—C17a1.3657 (18)C17—H170.9500
O11—C121.442 (2)N16—H16A0.89 (2)
C12—O131.434 (2)N16—H16B0.91 (2)
C12—H12A0.9900N31—C321.364 (2)
C12—H12B0.9900N31—H310.8800
O13—C13a1.3832 (19)C32—C331.469 (2)
C13a—C141.359 (2)C33—C341.368 (2)
C14—C151.430 (2)C34—C34a1.426 (2)
C14—H140.9500C34—H340.9500
C15—C161.423 (2)C34a—C351.410 (2)
C16—C171.416 (2)C35—C361.368 (2)
C17—C17a1.363 (2)C35—H350.9500
C13a—C17a1.386 (2)C36—C371.406 (2)
C16—N161.375 (2)C36—H360.9500
C15—C11.472 (2)C37—C381.375 (2)
C1—O11.2403 (19)C37—H370.9500
C1—C21.483 (2)C38—C38a1.398 (2)
C2—C31.340 (2)C38—H380.9500
C2—H20.9500C38a—N311.3777 (19)
C3—C331.453 (2)C34a—C38a1.403 (2)
C3—H30.9500C32—O321.2488 (18)
O1—C1—C15121.80 (14)O11—C17a—C13a110.22 (14)
O1—C1—C2119.23 (14)C16—N16—H16A117.4 (12)
C15—C1—C2118.97 (13)C16—N16—H16B113.9 (12)
C3—C2—C1119.74 (14)H16A—N16—H16B118.1 (17)
C3—C2—H2120.1C32—N31—C38a125.85 (13)
C1—C2—H2120.1C32—N31—H31117.1
C2—C3—C33128.11 (14)C38a—N31—H31117.1
C2—C3—H3115.9O32—C32—N31119.54 (14)
C33—C3—H3115.9O32—C32—C33124.36 (14)
C17a—O11—C12105.71 (12)N31—C32—C33116.10 (13)
O13—C12—O11107.92 (12)C34—C33—C3119.49 (14)
O13—C12—H12A110.1C34—C33—C32118.69 (14)
O11—C12—H12A110.1C3—C33—C32121.81 (13)
O13—C12—H12B110.1C33—C34—C34a123.01 (14)
O11—C12—H12B110.1C33—C34—H34118.5
H12A—C12—H12B108.4C34a—C34—H34118.5
C13a—O13—C12105.42 (12)C38a—C34a—C35118.71 (15)
C14—C13a—O13128.65 (14)C38a—C34a—C34117.71 (14)
C14—C13a—C17a121.43 (14)C35—C34a—C34123.58 (14)
O13—C13a—C17a109.77 (13)C36—C35—C34a120.51 (15)
C13a—C14—C15118.86 (14)C36—C35—H35119.7
C13a—C14—H14120.6C34a—C35—H35119.7
C15—C14—H14120.6C35—C36—C37120.04 (14)
C16—C15—C14118.74 (14)C35—C36—H36120.0
C16—C15—C1120.27 (14)C37—C36—H36120.0
C14—C15—C1120.96 (14)C38—C37—C36120.70 (15)
N16—C16—C17117.54 (14)C38—C37—H37119.7
N16—C16—C15122.06 (14)C36—C37—H37119.7
C17—C16—C15120.40 (14)C37—C38—C38a119.39 (15)
C17a—C17—C16117.81 (14)C37—C38—H38120.3
C17a—C17—H17121.1C38a—C38—H38120.3
C16—C17—H17121.1N31—C38a—C38120.73 (14)
C17—C17a—O11127.16 (15)N31—C38a—C34a118.62 (14)
C17—C17a—C13a122.58 (14)C38—C38a—C34a120.65 (14)
O1—C1—C2—C33.4 (2)C1—C2—C3—C33179.29 (14)
C17a—O11—C12—O139.62 (17)C2—C3—C33—C323.3 (3)
O11—C12—O13—C13a9.42 (17)C3—C2—C1—C15176.75 (14)
C12—O13—C13a—C17a5.76 (17)C2—C1—C15—C147.9 (2)
O13—C13a—C14—C15178.41 (15)C12—O13—C13a—C14178.72 (16)
C17a—C13a—C14—C153.3 (2)C12—O11—C17a—C17176.21 (16)
C13a—C14—C15—C160.7 (2)O32—C32—C33—C34179.55 (15)
C13a—C14—C15—C1178.64 (14)N31—C32—C33—C340.7 (2)
O1—C1—C15—C169.8 (2)O32—C32—C33—C30.8 (2)
C2—C1—C15—C16170.02 (14)N31—C32—C33—C3179.41 (13)
O1—C1—C15—C14172.27 (15)C3—C33—C34—C34a179.41 (14)
C14—C15—C16—N16176.04 (14)C32—C33—C34—C34a0.6 (2)
C1—C15—C16—N166.0 (2)C33—C34—C34a—C38a1.1 (2)
C14—C15—C16—C173.1 (2)C33—C34—C34a—C35179.78 (15)
C1—C15—C16—C17174.81 (13)C38a—C34a—C35—C361.2 (2)
N16—C16—C17—C17a174.87 (14)C34—C34a—C35—C36177.92 (15)
C15—C16—C17—C17a4.3 (2)C34a—C35—C36—C370.7 (2)
C16—C17—C17a—O11179.15 (14)C35—C36—C37—C380.5 (2)
C16—C17—C17a—C13a1.8 (2)C36—C37—C38—C38a1.0 (2)
C12—O11—C17a—C13a6.14 (18)C32—N31—C38a—C38178.25 (14)
C14—C13a—C17a—C172.1 (3)C32—N31—C38a—C34a1.7 (2)
O13—C13a—C17a—C17178.04 (14)C37—C38—C38a—N31179.64 (14)
C14—C13a—C17a—O11175.64 (14)C37—C38—C38a—C34a0.3 (2)
O13—C13a—C17a—O110.26 (18)C35—C34a—C38a—N31179.27 (14)
C38a—N31—C32—O32178.93 (14)C34—C34a—C38a—N311.5 (2)
C38a—N31—C32—C331.3 (2)C35—C34a—C38a—C380.7 (2)
C2—C3—C33—C34177.95 (15)C34—C34a—C38a—C38178.47 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N16—H16B···O10.91 (2)1.90 (2)2.620 (2)135 (2)
N31—H31···O32i0.881.892.768 (2)176
C35—H35···O1ii0.952.383.334 (2)177
Symmetry codes: (i) x1, y+1, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC19H14N2O4
Mr334.32
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)5.7799 (2), 9.9485 (3), 13.0849 (5)
α, β, γ (°)83.343 (2), 86.652 (2), 77.128 (2)
V3)728.13 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.10 × 0.06 × 0.06
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.989, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
9539, 2858, 2377
Rint0.033
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.112, 1.05
No. of reflections2858
No. of parameters232
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.24

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top
C13a—C141.359 (2)N31—C321.364 (2)
C14—C151.430 (2)C32—C331.469 (2)
C15—C161.423 (2)C33—C341.368 (2)
C16—C171.416 (2)C34—C34a1.426 (2)
C17—C17a1.363 (2)C34a—C351.410 (2)
C13a—C17a1.386 (2)C35—C361.368 (2)
C16—N161.375 (2)C36—C371.406 (2)
C15—C11.472 (2)C37—C381.375 (2)
C1—O11.2403 (19)C38—C38a1.398 (2)
C1—C21.483 (2)C38a—N311.3777 (19)
C2—C31.340 (2)C34a—C38a1.403 (2)
C3—C331.453 (2)C32—O321.2488 (18)
C1—C2—C3—C33179.29 (14)C2—C1—C15—C147.9 (2)
C2—C3—C33—C323.3 (3)C12—O13—C13a—C14178.72 (16)
C3—C2—C1—C15176.75 (14)C12—O11—C17a—C17176.21 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N16—H16B···O10.91 (2)1.90 (2)2.620 (2)135 (2)
N31—H31···O32i0.881.892.768 (2)176
C35—H35···O1ii0.952.383.334 (2)177
Symmetry codes: (i) x1, y+1, z+1; (ii) x+1, y, z+1.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds