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1-(6-Amino-1,3-benzodioxol-5-yl)-3-(3,4,5-tri­methoxy­phenyl)­prop-2-en-1-one, C19H19NO6, (I), contains an intramolecular N-H...O hydrogen bond and a weak C-H...O hydrogen bond, which forms a C(10) chain motif running parallel to the c axis. The 6-amino-1,3-benzo­dioxol-5-yl moieties are involved in [pi]-[pi] stacking. 1-(6-Amino-1,3-benzo­dioxol-5-yl)-3-[4-(N,N-di­methyl­amino)­phenyl]­prop-2-en-1-one, C18H18N2O3, (II), crystallizes with two mol­ecules in the asymmetric unit. The main feature of the supramolecular structure of (II) is the formation of a centrosymmetric hydrogen-bonded tetramer with an R84(16) motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101018297/gd1178sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101018297/gd1178Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101018297/gd1178IIsup3.hkl
Contains datablock II

CCDC references: 180169; 180170

Comment top

Many synthetic or naturally occurring compounds containing the 1,3-dioxolyl group in their structures are very important because of their pharmacological properties (Ma et al., 1987; Ohta & Kimoto, 1976; Schlunke & Egli, 1972; Krause & Goeber, 1972; Gabrielsen et al., 1992). Chalcones (1,3-diarylpropenones) have been widely used as starting materials in numerous synthetic reactions (Awad et al., 1960; Coudert et al., 1988; Carrie & Rochard, 1963), including the preparation of fused-ring heterocyclic compounds (Insuasty et al., 1992, 1997; Kolos et al., 1996). We have prepared the title compounds, (I) and (II), as intermediates in the synthesis of novel dihydroquinolinones. This is a class of compounds with interesting pharmaceutical properties (Pfizer, 1980; Jordis et al., 1991; Baker et al., 1990), since the 1,3-dioxolyl residue in their frameworks enhances their practical applications. \sch

The molecular structures of (I) and of the two independent molecules of (II) are shown in Figs. 1 and 2, respectively. The dioxol-5-yl groups in all three molecules have C2 envelope puckers. In (I), a strong intramolecular hydrogen bond is observed with an S(6) motif via N5—H5A···O8 (Bernstein et al., 1995) (Fig. 1, Table 1), and likewise in (II) via N15—H15A···O18 and N25—H25A···O28 (Fig. 2, Table 2).

The supramolecular structures of (I) and (II) are completely different. In (I), a C(10) motif is formed via C16—H16···O1(x, -1/2 - y, z - 1/2), creating a chain which runs parallel to the c axis. Two such anti-parallel chains are shown in Fig. 3. Atom H5B is not involved in any hydrogen bonding. In (II), however, the equivalent H atoms H15B and H25B are involved in strong hydrogen bonds via N15—N15B···O28(1 - x, 1 - y, 1 - z) and N25—H25B···O18, linking molecules 1 and 2 to form a tetramer with an R84(16) motif (Fig. 4). Such motifs occur centred at (l + 1/2, m + 1/2, n + 1/2), where l, m and n are integer or zero. The weak C14—H14···O28(1 - x, 1 - y, 1 - z) and C24—H24···O18 hydrogen bonds help to reinforce this tetramer structure. The tetramers are linked to each other by weak hydrogen bonds via C212—H212···O13(x, y, z - 1) and C212(1 - x, 1 - y, z)-H212(1 - x, 1 - y, z)···O13(1 - x, 1 - y, 1 - z), which form bridging R44(26) rings along with the N15—H15···O28 hydrogen bonds of the tetramer (Fig. 5).

In (I), there is π···π stacking between the benzo-1,3-dioxol-5-yl groups, where the rings defined by O1—C2—O3—C3a—C7a and C3a—C4—C5—C6—C7—C7a are stacked such that the distance between the centres of gravity of the rings is 3.7276 (9) Å, the dihedral angle is 3.50°, the perpendicular distance from the centre of gravity of the former ring at (x, y, z) to the latter at (x, 1 + y, z) is 3.368 Å and the perpendicular distance from the centre of gravity of the latter ring at (x, y, z) to the former at (x, y - 1, z) is 3.445 Å (Fig. 6). It is worth noting that the dihedral angle between these planes, 3.50°, is in fact the dihedral angle between the two components of the benzo-1,3-dioxol-5-yl group, which is not in itself planar. There is no ππ stacking in (II).

Experimental top

For (I), a mixture of 6'-amino-3',4'-(methylenedioxy)acetophenone (0.50 g, 2.79 mmol), 3,4,5-trimethoxybenzaldehyde (2.79 mmol), ethanol (10 ml) and NaOH (0.5 ml, 20% aq.) was heated to 333–343 K for 10–15 min and the reaction monitored by thin-layer chromatography. After cooling, the solid formed was filtered and washed with ethanol to yield pure (I) as orange crystals (93% yield; m.p. 464 K). For (II), a mixture of 6'-amino-3',4'-(methylenedioxy)acetophenone (0.50 g, 2.79 mmol), 4-(N,N-dimethylamino)benzaldehyde (2.79 mmol), ethanol (10 ml) and NaOH (0.5 ml, 20% aq.) was heated to 333–343 K for 10–15 min and the reaction monitored by thin-layer chromatography. After cooling, the solid formed was filtered and washed with ethanol to yield pure (II) as purple crystals (46% yield; m.p. 435 K). For both (I) and (II), crystals suitable for single-crystal X-ray diffraction were selected directly from the prepared samples.

Refinement top

For both compounds, H atoms were treated as riding, with C—H = 0.95 to 0.99 Å. In the case of the N—H bonds, the H atoms were initially located on a difference Fourier map. The bond lengths were then DFIXed (SHELXL97; Sheldrick, 1997) to 0.880 Å with an e.s.d. of 0.005 until a value close to 0.88 Å was obtained, at which stage they were AFIXed (SHELXL97) and allowed to ride on their parent atoms.

Computing details top

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A molecular view of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Views of the two independent molecules of (II) with the atom-numbering schemes. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. A view of the crystal structure of (I) looking down the b axis, showing two anti-parallel C(10) chains [symmetry code: (i) x, -1/2 - y, z - 1/2].
[Figure 4] Fig. 4. A view of the tetramer formed by the molecules of (II) at (x, y, z) and (1 - x, 1 - y, 1 - z). For the sake of clarity, H atoms bonded to C have been omitted [symmetry code: (ii) 1 - x, 1 - y, 1 - z].
[Figure 5] Fig. 5. A view of the R44(26) rings which link the tetramers in (II) [symmetry codes: (ii) 1 - x, 1 - y, 1 - z; (iii) x, y, z - 1; (iv) 1 - x, 1 - y, -z]. For the sake of clarity, H atoms bonded to C or N and not involved in this motif are omitted, as is the unit-cell box.
[Figure 6] Fig. 6. A view of the π···π stacking in (I). For the sake of clarity the unit-cell box has been omitted.
(I) 1-(6-amino-1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C19H19NO6Dx = 1.451 Mg m3
Mr = 357.35Melting point: 464 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 23.5477 (4) ÅCell parameters from 3622 reflections
b = 4.9605 (1) Åθ = 3.1–27.5°
c = 14.2556 (8) ŵ = 0.11 mm1
β = 100.702 (1)°T = 150 K
V = 1636.21 (10) Å3Block, orange
Z = 40.4 × 0.1 × 0.1 mm
F(000) = 752
Data collection top
Nonius KappaCCD
diffractometer
3622 independent reflections
Radiation source: fine-focus sealed X-ray tube2832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 3030
Tmin = 0.958, Tmax = 0.989k = 66
11152 measured reflectionsl = 1818
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3552P]
where P = (Fo2 + 2Fc2)/3
3622 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C19H19NO6V = 1636.21 (10) Å3
Mr = 357.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 23.5477 (4) ŵ = 0.11 mm1
b = 4.9605 (1) ÅT = 150 K
c = 14.2556 (8) Å0.4 × 0.1 × 0.1 mm
β = 100.702 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3622 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
2832 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.989Rint = 0.048
11152 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å3
3622 reflectionsΔρmin = 0.32 e Å3
238 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16792 (4)0.9086 (2)0.04794 (8)0.0228 (3)
C20.12417 (6)1.0264 (3)0.02328 (11)0.0216 (3)
O30.06873 (4)0.9492 (2)0.00242 (8)0.0228 (3)
C3a0.07999 (6)0.7506 (3)0.06504 (10)0.0180 (3)
C40.04112 (6)0.5963 (3)0.10051 (10)0.0180 (3)
C50.06256 (6)0.3950 (3)0.16848 (10)0.0163 (3)
N50.02326 (5)0.2365 (2)0.20091 (9)0.0203 (3)
C60.12324 (6)0.3693 (3)0.20219 (10)0.0160 (3)
C70.16178 (6)0.5382 (3)0.16234 (10)0.0183 (3)
C7a0.13948 (6)0.7212 (3)0.09496 (11)0.0171 (3)
C80.14568 (6)0.1787 (3)0.27912 (10)0.0169 (3)
O80.11443 (4)0.0101 (2)0.30938 (7)0.0210 (3)
C90.20706 (6)0.2028 (3)0.32790 (11)0.0195 (3)
C100.22878 (6)0.0449 (3)0.40162 (11)0.0188 (3)
C110.28618 (6)0.0587 (3)0.46207 (10)0.0179 (3)
C120.32891 (6)0.2392 (3)0.44517 (10)0.0180 (3)
C130.38233 (6)0.2436 (3)0.50627 (11)0.0180 (3)
O130.42754 (4)0.4040 (2)0.49442 (8)0.0219 (3)
C1310.42037 (7)0.5680 (3)0.41009 (12)0.0243 (4)
C140.39292 (6)0.0760 (3)0.58688 (11)0.0185 (3)
O140.44395 (4)0.1016 (2)0.65090 (7)0.0227 (3)
C1410.48413 (7)0.1152 (3)0.64751 (12)0.0252 (4)
C150.35021 (7)0.1042 (3)0.60318 (10)0.0192 (3)
O150.36428 (5)0.2597 (2)0.68360 (8)0.0255 (3)
C1510.32121 (7)0.4413 (3)0.70400 (12)0.0270 (4)
C160.29745 (6)0.1155 (3)0.54069 (10)0.0187 (3)
H2A0.12800.96110.08740.026*
H2B0.12801.22520.02220.026*
H40.00070.62270.08030.022*
H5A0.03560.09080.23370.024*
H5B0.01210.23770.16730.024*
H70.20240.52250.18280.022*
H90.23120.33300.30620.023*
H100.20400.09320.41670.023*
H120.32140.35820.39210.022*
H13A0.40940.45380.35350.036*
H13B0.45680.66020.40710.036*
H13C0.39000.70200.41210.036*
H14A0.46550.28730.65680.038*
H14B0.51810.09050.69810.038*
H14C0.49620.11540.58530.038*
H15A0.28770.33870.71590.041*
H15B0.33700.54800.76070.041*
H15C0.30930.56200.64950.041*
H160.26890.24160.55130.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0178 (5)0.0245 (6)0.0260 (6)0.0017 (4)0.0043 (5)0.0090 (4)
C20.0208 (8)0.0234 (8)0.0200 (8)0.0017 (6)0.0028 (6)0.0049 (6)
O30.0191 (6)0.0259 (6)0.0228 (6)0.0044 (4)0.0026 (4)0.0079 (4)
C3a0.0196 (8)0.0185 (7)0.0150 (7)0.0039 (6)0.0009 (6)0.0007 (5)
C40.0136 (7)0.0203 (7)0.0188 (8)0.0026 (5)0.0002 (6)0.0022 (6)
C50.0148 (7)0.0174 (7)0.0166 (7)0.0004 (5)0.0023 (6)0.0035 (5)
N50.0147 (6)0.0198 (6)0.0258 (7)0.0010 (5)0.0019 (5)0.0019 (5)
C60.0165 (7)0.0142 (7)0.0168 (7)0.0018 (5)0.0018 (6)0.0018 (5)
C70.0129 (7)0.0218 (7)0.0195 (8)0.0019 (6)0.0012 (6)0.0013 (6)
C7a0.0164 (7)0.0175 (7)0.0180 (8)0.0007 (5)0.0048 (6)0.0005 (5)
C80.0172 (7)0.0168 (7)0.0168 (7)0.0012 (5)0.0036 (6)0.0029 (5)
O80.0198 (5)0.0194 (5)0.0230 (6)0.0021 (4)0.0021 (4)0.0026 (4)
C90.0162 (7)0.0220 (7)0.0202 (8)0.0009 (6)0.0028 (6)0.0022 (6)
C100.0170 (7)0.0193 (7)0.0199 (8)0.0003 (6)0.0026 (6)0.0007 (6)
C110.0163 (7)0.0209 (7)0.0164 (8)0.0031 (6)0.0026 (6)0.0012 (6)
C120.0180 (7)0.0190 (7)0.0163 (8)0.0028 (6)0.0016 (6)0.0004 (6)
C130.0179 (7)0.0159 (7)0.0203 (8)0.0004 (5)0.0035 (6)0.0027 (6)
O130.0187 (6)0.0223 (6)0.0233 (6)0.0044 (4)0.0001 (4)0.0025 (4)
C1310.0238 (8)0.0217 (8)0.0272 (9)0.0038 (6)0.0043 (7)0.0048 (6)
C140.0159 (7)0.0203 (7)0.0176 (8)0.0019 (6)0.0013 (6)0.0034 (6)
O140.0197 (6)0.0223 (6)0.0223 (6)0.0027 (4)0.0059 (4)0.0029 (4)
C1410.0187 (8)0.0256 (8)0.0284 (9)0.0033 (6)0.0026 (7)0.0016 (6)
C150.0217 (8)0.0188 (7)0.0167 (8)0.0040 (6)0.0027 (6)0.0009 (6)
O150.0245 (6)0.0297 (6)0.0207 (6)0.0004 (5)0.0005 (5)0.0095 (4)
C1510.0289 (9)0.0262 (8)0.0267 (9)0.0020 (7)0.0070 (7)0.0085 (6)
C160.0180 (7)0.0171 (7)0.0210 (8)0.0001 (5)0.0036 (6)0.0003 (6)
Geometric parameters (Å, º) top
O1—C7a1.3887 (17)C11—C121.401 (2)
O1—C21.4301 (19)C11—C161.401 (2)
C2—O31.4436 (18)C12—C131.391 (2)
C2—H2A0.9900C12—H120.9500
C2—H2B0.9900C13—O131.3646 (17)
O3—C3a1.3677 (17)C13—C141.403 (2)
C3a—C41.361 (2)O13—C1311.4352 (18)
C3a—C7a1.394 (2)C131—H13A0.9800
C4—C51.417 (2)C131—H13B0.9800
C4—H40.9500C131—H13C0.9800
C5—N51.3594 (18)C14—O141.3732 (18)
C5—C61.426 (2)C14—C151.397 (2)
N5—H5A0.8801O14—C1411.4392 (18)
N5—H5B0.8800C141—H14A0.9800
C6—C71.428 (2)C141—H14B0.9800
C6—C81.470 (2)C141—H14C0.9800
C7—C7a1.355 (2)C15—O151.3704 (18)
C7—H70.9500C15—C161.389 (2)
C8—O81.2431 (17)O15—C1511.4262 (19)
C8—C91.488 (2)C151—H15A0.9800
C9—C101.334 (2)C151—H15B0.9800
C9—H90.9500C151—H15C0.9800
C10—C111.463 (2)C16—H160.9500
C10—H100.9500
C7a—O1—C2105.54 (11)C12—C11—C10122.89 (13)
O1—C2—O3107.76 (11)C16—C11—C10117.35 (13)
O1—C2—H2A110.2C13—C12—C11119.83 (13)
O3—C2—H2A110.2C13—C12—H12120.1
O1—C2—H2B110.2C11—C12—H12120.1
O3—C2—H2B110.2O13—C13—C12124.57 (13)
H2A—C2—H2B108.5O13—C13—C14115.02 (13)
C3a—O3—C2105.75 (11)C12—C13—C14120.41 (13)
C4—C3a—O3127.62 (13)C13—O13—C131117.45 (11)
C4—C3a—C7a122.31 (13)O13—C131—H13A109.5
O3—C3a—C7a110.06 (12)O13—C131—H13B109.5
C3a—C4—C5118.13 (13)H13A—C131—H13B109.5
C3a—C4—H4120.9O13—C131—H13C109.5
C5—C4—H4120.9H13A—C131—H13C109.5
N5—C5—C4117.48 (13)H13B—C131—H13C109.5
N5—C5—C6122.44 (13)O14—C14—C15121.12 (13)
C4—C5—C6120.06 (13)O14—C14—C13119.35 (13)
C5—N5—H5A118.5C15—C14—C13119.44 (13)
C5—N5—H5B116.5C14—O14—C141114.08 (11)
H5A—N5—H5B118.7O14—C141—H14A109.5
C5—C6—C7118.96 (13)O14—C141—H14B109.5
C5—C6—C8120.53 (13)H14A—C141—H14B109.5
C7—C6—C8120.47 (13)O14—C141—H14C109.5
C7a—C7—C6118.94 (13)H14A—C141—H14C109.5
C7a—C7—H7120.5H14B—C141—H14C109.5
C6—C7—H7120.5O15—C15—C16124.23 (13)
C7—C7a—O1129.24 (13)O15—C15—C14115.44 (13)
C7—C7a—C3a121.48 (13)C16—C15—C14120.32 (13)
O1—C7a—C3a109.24 (12)C15—O15—C151117.08 (12)
O8—C8—C6122.52 (13)O15—C151—H15A109.5
O8—C8—C9118.57 (13)O15—C151—H15B109.5
C6—C8—C9118.71 (12)H15A—C151—H15B109.5
C10—C9—C8121.19 (13)O15—C151—H15C109.5
C10—C9—H9119.4H15A—C151—H15C109.5
C8—C9—H9119.4H15B—C151—H15C109.5
C9—C10—C11127.83 (14)C15—C16—C11120.16 (13)
C9—C10—H10116.1C15—C16—H16119.9
C11—C10—H10116.1C11—C16—H16119.9
C12—C11—C16119.75 (13)
C7a—O1—C2—O312.88 (15)C6—C8—C9—C10176.25 (13)
O1—C2—O3—C3a12.08 (15)C8—C9—C10—C11174.20 (13)
C2—O3—C3a—C4173.10 (14)C9—C10—C11—C124.3 (2)
C2—O3—C3a—C7a6.61 (15)C9—C10—C11—C16174.68 (15)
O3—C3a—C4—C5178.10 (13)C16—C11—C12—C130.3 (2)
C7a—C3a—C4—C51.6 (2)C10—C11—C12—C13179.21 (13)
C3a—C4—C5—N5177.85 (12)C11—C12—C13—O13177.52 (13)
C3a—C4—C5—C63.8 (2)C11—C12—C13—C142.5 (2)
N5—C5—C6—C7178.10 (13)C12—C13—O13—C1313.7 (2)
C4—C5—C6—C73.6 (2)C14—C13—O13—C131176.36 (12)
N5—C5—C6—C84.0 (2)O13—C13—C14—O145.97 (19)
C4—C5—C6—C8174.26 (13)C12—C13—C14—O14173.98 (13)
C5—C6—C7—C7a1.2 (2)O13—C13—C14—C15177.30 (12)
C8—C6—C7—C7a176.67 (13)C12—C13—C14—C152.7 (2)
C6—C7—C7a—O1178.55 (13)C15—C14—O14—C14176.27 (17)
C6—C7—C7a—C3a1.0 (2)C13—C14—O14—C141107.06 (15)
C2—O1—C7a—C7173.31 (15)O14—C14—C15—O153.3 (2)
C2—O1—C7a—C3a8.92 (15)C13—C14—C15—O15179.96 (12)
C4—C3a—C7a—C70.8 (2)O14—C14—C15—C16175.99 (13)
O3—C3a—C7a—C7179.42 (13)C13—C14—C15—C160.7 (2)
C4—C3a—C7a—O1178.82 (13)C16—C15—O15—C1510.8 (2)
O3—C3a—C7a—O11.45 (16)C14—C15—O15—C151178.41 (12)
C5—C6—C8—O89.4 (2)O15—C15—C16—C11177.63 (13)
C7—C6—C8—O8172.82 (13)C14—C15—C16—C111.6 (2)
C5—C6—C8—C9165.62 (13)C12—C11—C16—C151.8 (2)
C7—C6—C8—C912.2 (2)C10—C11—C16—C15177.21 (13)
O8—C8—C9—C101.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O80.882.012.651 (2)129
C16—H16···O1i0.952.513.398 (2)155
Symmetry code: (i) x, y+1/2, z+1/2.
(II) 1-(6-amino-1,3-benzodioxol-5-yl)-3-[4-(N,N-dimethylamino)phenyl]prop-2-en-1-one top
Crystal data top
C18H18N2O3F(000) = 656
Mr = 310.34Dx = 1.339 Mg m3
Triclinic, P1Melting point: 435 K
a = 9.5849 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3218 (4) ÅCell parameters from 6884 reflections
c = 13.3304 (4) Åθ = 3.1–27.5°
α = 83.4617 (14)°µ = 0.09 mm1
β = 80.2411 (17)°T = 150 K
γ = 85.7271 (16)°Block, orange
V = 1539.04 (8) Å30.22 × 0.14 × 0.12 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
6884 independent reflections
Radiation source: fine-focus sealed X-ray tube4873 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.085
ϕ and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.980, Tmax = 0.989k = 1515
23078 measured reflectionsl = 1717
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0927P)2]
where P = (Fo2 + 2Fc2)/3
6884 reflections(Δ/σ)max = 0.006
419 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C18H18N2O3γ = 85.7271 (16)°
Mr = 310.34V = 1539.04 (8) Å3
Triclinic, P1Z = 4
a = 9.5849 (2) ÅMo Kα radiation
b = 12.3218 (4) ŵ = 0.09 mm1
c = 13.3304 (4) ÅT = 150 K
α = 83.4617 (14)°0.22 × 0.14 × 0.12 mm
β = 80.2411 (17)°
Data collection top
Nonius KappaCCD
diffractometer
6884 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4873 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.989Rint = 0.085
23078 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å3
6884 reflectionsΔρmin = 0.34 e Å3
419 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.02777 (11)0.75297 (9)0.87894 (8)0.0362 (3)
C120.01144 (17)0.65439 (14)0.94317 (13)0.0349 (4)
O130.13044 (11)0.60803 (9)0.91563 (8)0.0324 (3)
C13a0.18474 (15)0.66717 (12)0.82576 (11)0.0257 (3)
C140.30993 (15)0.64707 (12)0.76417 (11)0.0276 (3)
C150.34538 (15)0.72053 (12)0.67488 (11)0.0259 (3)
N150.47153 (13)0.69853 (11)0.61323 (10)0.0333 (3)
C160.25060 (15)0.81109 (11)0.65143 (11)0.0237 (3)
C170.12044 (16)0.82630 (12)0.71898 (11)0.0270 (3)
C17a0.09087 (15)0.75469 (12)0.80356 (12)0.0266 (3)
C180.28570 (16)0.88751 (12)0.55863 (11)0.0261 (3)
O180.39602 (11)0.87251 (9)0.49523 (8)0.0306 (3)
C190.19130 (16)0.98540 (12)0.54110 (12)0.0274 (3)
C1100.22813 (16)1.06686 (12)0.46786 (12)0.0281 (3)
C1110.14871 (16)1.17030 (12)0.44964 (12)0.0267 (3)
C1120.02860 (16)1.20526 (12)0.51632 (12)0.0283 (3)
C1130.04435 (16)1.30398 (12)0.49728 (12)0.0281 (3)
C1140.00003 (15)1.37594 (12)0.40891 (12)0.0269 (3)
N1410.07035 (14)1.47595 (11)0.39143 (10)0.0320 (3)
C1420.20735 (17)1.50204 (14)0.45120 (14)0.0376 (4)
C1430.02794 (18)1.54618 (13)0.29822 (13)0.0373 (4)
C1150.11977 (16)1.34160 (13)0.34170 (12)0.0291 (4)
C1160.19116 (16)1.24217 (12)0.36211 (12)0.0290 (4)
O210.13133 (15)0.90490 (9)0.04973 (10)0.0502 (4)
C220.0878 (2)1.00143 (14)0.09912 (14)0.0450 (5)
O230.16077 (14)0.99874 (9)0.18490 (9)0.0467 (3)
C23a0.21602 (17)0.89328 (12)0.19967 (12)0.0320 (4)
C240.28336 (17)0.84841 (13)0.27696 (12)0.0304 (4)
C250.33276 (15)0.73703 (12)0.27643 (11)0.0253 (3)
N250.39928 (14)0.69207 (11)0.35479 (10)0.0324 (3)
C260.31367 (15)0.67600 (12)0.19510 (11)0.0239 (3)
C270.24427 (16)0.72964 (12)0.11530 (11)0.0284 (3)
C27a0.19712 (17)0.83555 (13)0.11942 (12)0.0312 (4)
C280.35989 (14)0.56004 (12)0.19606 (11)0.0237 (3)
O280.40653 (11)0.50868 (8)0.27099 (8)0.0285 (3)
C290.35032 (15)0.50120 (12)0.10696 (11)0.0258 (3)
C2100.37997 (15)0.39319 (12)0.10832 (11)0.0250 (3)
C2110.37359 (15)0.32496 (12)0.02711 (11)0.0255 (3)
C2120.33357 (15)0.36544 (12)0.06698 (12)0.0268 (3)
C2130.32193 (16)0.29851 (13)0.14029 (12)0.0309 (4)
C2140.35218 (17)0.18441 (13)0.12406 (14)0.0365 (4)
N2410.34161 (19)0.11719 (13)0.19717 (14)0.0573 (5)
C2420.2858 (2)0.15843 (17)0.28887 (16)0.0574 (6)
C2430.3883 (2)0.00276 (15)0.18392 (17)0.0534 (5)
C2150.39294 (19)0.14362 (13)0.03017 (14)0.0405 (4)
C2160.40253 (18)0.21184 (13)0.04283 (13)0.0342 (4)
H12A0.08120.60230.93440.042*
H12B0.02790.66951.01570.042*
H140.37160.58600.78030.033*
H15A0.50670.74480.56140.040*
H15B0.52980.64750.63750.040*
H170.05530.88580.70490.032*
H190.10110.99100.58320.033*
H1100.31521.05580.42320.034*
H1120.00351.15920.57670.034*
H1130.12571.32410.54420.034*
H14A0.27631.45190.43950.056*
H14B0.23901.57750.43050.056*
H14C0.19931.49440.52400.056*
H14D0.07541.55020.28580.056*
H14E0.07281.61960.30510.056*
H14F0.05771.51620.24060.056*
H1150.15231.38740.28130.035*
H1160.27221.22160.31510.035*
H22A0.01591.00430.12250.054*
H22B0.11141.06720.05090.054*
H240.29710.89010.32990.036*
H25A0.42530.62190.35740.039*
H25B0.40540.73430.40260.039*
H270.23120.69150.05980.034*
H290.32250.54090.04750.031*
H2100.40830.35700.16910.030*
H2120.31380.44190.08050.032*
H2130.29320.32920.20270.037*
H24A0.18700.18550.27060.086*
H24B0.29030.09950.33310.086*
H24C0.34220.21830.32530.086*
H24D0.48630.00370.17080.080*
H24E0.38330.03120.24610.080*
H24F0.32690.03440.12580.080*
H2150.41430.06740.01670.049*
H2160.42960.18130.10590.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0333 (6)0.0315 (6)0.0379 (6)0.0076 (5)0.0028 (5)0.0022 (5)
C120.0290 (8)0.0343 (9)0.0386 (9)0.0051 (7)0.0045 (7)0.0024 (7)
O130.0296 (6)0.0312 (6)0.0332 (6)0.0042 (5)0.0019 (5)0.0026 (5)
C13a0.0273 (8)0.0238 (8)0.0272 (8)0.0015 (6)0.0089 (7)0.0014 (6)
C140.0255 (8)0.0251 (8)0.0332 (8)0.0025 (6)0.0099 (7)0.0019 (7)
C150.0247 (7)0.0261 (8)0.0295 (8)0.0021 (6)0.0090 (7)0.0061 (6)
N150.0269 (7)0.0334 (8)0.0369 (8)0.0041 (6)0.0038 (6)0.0019 (6)
C160.0252 (7)0.0210 (7)0.0273 (8)0.0011 (6)0.0092 (6)0.0057 (6)
C170.0280 (8)0.0213 (8)0.0332 (8)0.0030 (6)0.0095 (7)0.0054 (6)
C17a0.0239 (7)0.0257 (8)0.0307 (8)0.0013 (6)0.0052 (7)0.0059 (6)
C180.0306 (8)0.0234 (8)0.0275 (8)0.0022 (6)0.0107 (7)0.0064 (6)
O180.0347 (6)0.0284 (6)0.0286 (6)0.0007 (5)0.0045 (5)0.0046 (5)
C190.0288 (8)0.0257 (8)0.0297 (8)0.0017 (6)0.0091 (7)0.0042 (6)
C1100.0310 (8)0.0273 (8)0.0281 (8)0.0008 (6)0.0095 (7)0.0059 (6)
C1110.0298 (8)0.0225 (8)0.0300 (8)0.0040 (6)0.0090 (7)0.0040 (6)
C1120.0326 (8)0.0252 (8)0.0279 (8)0.0052 (6)0.0068 (7)0.0003 (6)
C1130.0283 (8)0.0279 (8)0.0290 (8)0.0031 (6)0.0054 (7)0.0048 (6)
C1140.0276 (8)0.0232 (8)0.0318 (8)0.0041 (6)0.0097 (7)0.0020 (6)
N1410.0322 (7)0.0243 (7)0.0382 (8)0.0003 (5)0.0055 (6)0.0010 (6)
C1420.0339 (9)0.0298 (9)0.0488 (10)0.0021 (7)0.0082 (8)0.0032 (8)
C1430.0408 (10)0.0281 (9)0.0426 (10)0.0016 (7)0.0104 (8)0.0035 (7)
C1150.0318 (8)0.0252 (8)0.0304 (8)0.0067 (6)0.0063 (7)0.0010 (6)
C1160.0308 (8)0.0273 (8)0.0297 (8)0.0043 (6)0.0063 (7)0.0027 (7)
O210.0801 (10)0.0292 (7)0.0479 (7)0.0240 (6)0.0353 (7)0.0126 (6)
C220.0637 (12)0.0303 (10)0.0448 (10)0.0160 (8)0.0234 (10)0.0106 (8)
O230.0724 (9)0.0268 (6)0.0466 (7)0.0196 (6)0.0289 (7)0.0133 (5)
C23a0.0386 (9)0.0224 (8)0.0350 (9)0.0075 (7)0.0083 (8)0.0063 (7)
C240.0377 (9)0.0261 (8)0.0286 (8)0.0019 (7)0.0066 (7)0.0090 (6)
C250.0247 (7)0.0254 (8)0.0247 (8)0.0015 (6)0.0030 (6)0.0023 (6)
N250.0431 (8)0.0278 (7)0.0285 (7)0.0072 (6)0.0121 (6)0.0081 (6)
C260.0235 (7)0.0232 (8)0.0247 (7)0.0010 (6)0.0035 (6)0.0036 (6)
C270.0346 (8)0.0250 (8)0.0269 (8)0.0025 (6)0.0084 (7)0.0060 (6)
C27a0.0383 (9)0.0255 (8)0.0307 (8)0.0067 (7)0.0117 (7)0.0039 (7)
C280.0203 (7)0.0239 (8)0.0254 (8)0.0007 (6)0.0000 (6)0.0024 (6)
O280.0322 (6)0.0256 (6)0.0279 (6)0.0041 (4)0.0085 (5)0.0015 (4)
C290.0262 (8)0.0240 (8)0.0267 (8)0.0004 (6)0.0040 (6)0.0020 (6)
C2100.0249 (7)0.0228 (8)0.0269 (8)0.0002 (6)0.0043 (6)0.0015 (6)
C2110.0235 (7)0.0221 (8)0.0305 (8)0.0011 (6)0.0034 (6)0.0035 (6)
C2120.0257 (8)0.0227 (8)0.0316 (8)0.0015 (6)0.0039 (7)0.0037 (6)
C2130.0307 (8)0.0307 (9)0.0325 (8)0.0065 (6)0.0098 (7)0.0070 (7)
C2140.0358 (9)0.0301 (9)0.0490 (10)0.0060 (7)0.0177 (8)0.0164 (8)
N2410.0762 (12)0.0387 (9)0.0716 (11)0.0214 (8)0.0473 (10)0.0315 (8)
C2420.0737 (14)0.0504 (12)0.0606 (13)0.0082 (10)0.0370 (12)0.0275 (10)
C2430.0627 (13)0.0340 (10)0.0730 (14)0.0085 (9)0.0273 (11)0.0280 (10)
C2150.0496 (11)0.0219 (8)0.0540 (11)0.0061 (7)0.0203 (9)0.0092 (8)
C2160.0428 (9)0.0230 (8)0.0382 (9)0.0042 (7)0.0134 (8)0.0030 (7)
Geometric parameters (Å, º) top
O11—C17a1.3838 (18)O21—C27a1.3888 (18)
O11—C121.4189 (19)O21—C221.426 (2)
C12—O131.4399 (18)C22—O231.434 (2)
C12—H12A0.9900C22—H22A0.9900
C12—H12B0.9900C22—H22B0.9900
O13—C13a1.3723 (18)O23—C23a1.3721 (18)
C13a—C141.358 (2)C23a—C241.351 (2)
C13a—C17a1.390 (2)C23a—C27a1.393 (2)
C14—C151.419 (2)C24—C251.418 (2)
C14—H140.9500C24—H240.9500
C15—N151.3696 (19)C25—N251.3587 (18)
C15—C161.426 (2)C25—C261.431 (2)
N15—H15A0.8805N25—H25A0.8799
N15—H15B0.8805N25—H25B0.8799
C16—C171.423 (2)C26—C271.423 (2)
C16—C181.473 (2)C26—C281.463 (2)
C17—C17a1.354 (2)C27—C27a1.353 (2)
C17—H170.9500C27—H270.9500
C18—O181.2529 (18)C28—O281.2503 (16)
C18—C191.474 (2)C28—C291.479 (2)
C19—C1101.341 (2)C29—C2101.339 (2)
C19—H190.9500C29—H290.9500
C110—C1111.453 (2)C210—C2111.456 (2)
C110—H1100.9500C210—H2100.9500
C111—C1121.403 (2)C211—C2161.400 (2)
C111—C1161.403 (2)C211—C2121.400 (2)
C112—C1131.377 (2)C212—C2131.372 (2)
C112—H1120.9500C212—H2120.9500
C113—C1141.415 (2)C213—C2141.414 (2)
C113—H1130.9500C213—H2130.9500
C114—N1411.375 (2)C214—N2411.370 (2)
C114—C1151.402 (2)C214—C2151.402 (2)
N141—C1431.447 (2)N241—C2421.442 (2)
N141—C1421.450 (2)N241—C2431.448 (2)
C142—H14A0.9800C242—H24A0.9800
C142—H14B0.9800C242—H24B0.9800
C142—H14C0.9800C242—H24C0.9800
C143—H14D0.9800C243—H24D0.9800
C143—H14E0.9800C243—H24E0.9800
C143—H14F0.9800C243—H24F0.9800
C115—C1161.380 (2)C215—C2161.375 (2)
C115—H1150.9500C215—H2150.9500
C116—H1160.9500C216—H2160.9500
C17a—O11—C12105.70 (12)C27a—O21—C22105.18 (12)
O11—C12—O13108.42 (12)O21—C22—O23108.08 (13)
O11—C12—H12A110.0O21—C22—H22A110.1
O13—C12—H12A110.0O23—C22—H22A110.1
O11—C12—H12B110.0O21—C22—H22B110.1
O13—C12—H12B110.0O23—C22—H22B110.1
H12A—C12—H12B108.4H22A—C22—H22B108.4
C13a—O13—C12105.32 (11)C23a—O23—C22105.49 (12)
C14—C13a—O13127.44 (13)C24—C23a—O23127.47 (14)
C14—C13a—C17a122.64 (14)C24—C23a—C27a122.70 (14)
O13—C13a—C17a109.92 (13)O23—C23a—C27a109.80 (13)
C13a—C14—C15117.67 (13)C23a—C24—C25117.76 (14)
C13a—C14—H14121.2C23a—C24—H24121.1
C15—C14—H14121.2C25—C24—H24121.1
N15—C15—C14116.89 (13)N25—C25—C24117.51 (13)
N15—C15—C16122.78 (13)N25—C25—C26122.04 (13)
C14—C15—C16120.33 (14)C24—C25—C26120.45 (13)
C15—N15—H15A122.3C25—N25—H25A118.2
C15—N15—H15B117.1C25—N25—H25B116.8
H15A—N15—H15B117.9H25A—N25—H25B124.7
C15—C16—C17118.87 (13)C27—C26—C25118.47 (13)
C15—C16—C18120.86 (14)C27—C26—C28120.83 (13)
C17—C16—C18120.27 (13)C25—C26—C28120.65 (12)
C17a—C17—C16118.98 (13)C27a—C27—C26119.19 (14)
C17a—C17—H17120.5C27a—C27—H27120.4
C16—C17—H17120.5C26—C27—H27120.4
C17—C17a—O11129.04 (14)C27—C27a—O21129.36 (14)
C17—C17a—C13a121.50 (14)C27—C27a—C23a121.40 (14)
O11—C17a—C13a109.46 (13)O21—C27a—C23a109.20 (13)
O18—C18—C16121.41 (13)O28—C28—C26121.61 (13)
O18—C18—C19119.10 (13)O28—C28—C29118.80 (13)
C16—C18—C19119.47 (14)C26—C28—C29119.59 (12)
C110—C19—C18122.37 (15)C210—C29—C28121.41 (13)
C110—C19—H19118.8C210—C29—H29119.3
C18—C19—H19118.8C28—C29—H29119.3
C19—C110—C111126.78 (15)C29—C210—C211127.26 (13)
C19—C110—H110116.6C29—C210—H210116.4
C111—C110—H110116.6C211—C210—H210116.4
C112—C111—C116116.10 (14)C216—C211—C212116.54 (14)
C112—C111—C110123.52 (14)C216—C211—C210119.89 (13)
C116—C111—C110120.38 (14)C212—C211—C210123.51 (13)
C113—C112—C111122.27 (14)C213—C212—C211122.29 (14)
C113—C112—H112118.9C213—C212—H212118.9
C111—C112—H112118.9C211—C212—H212118.9
C112—C113—C114121.06 (15)C212—C213—C214120.81 (14)
C112—C113—H113119.5C212—C213—H213119.6
C114—C113—H113119.5C214—C213—H213119.6
N141—C114—C115121.85 (14)N241—C214—C215121.80 (15)
N141—C114—C113121.07 (14)N241—C214—C213121.12 (15)
C115—C114—C113117.07 (14)C215—C214—C213117.08 (14)
C114—N141—C143120.31 (14)C214—N241—C242121.17 (15)
C114—N141—C142120.86 (13)C214—N241—C243120.16 (15)
C143—N141—C142117.10 (13)C242—N241—C243118.66 (15)
N141—C142—H14A109.5N241—C242—H24A109.5
N141—C142—H14B109.5N241—C242—H24B109.5
H14A—C142—H14B109.5H24A—C242—H24B109.5
N141—C142—H14C109.5N241—C242—H24C109.5
H14A—C142—H14C109.5H24A—C242—H24C109.5
H14B—C142—H14C109.5H24B—C242—H24C109.5
N141—C143—H14D109.5N241—C243—H24D109.5
N141—C143—H14E109.5N241—C243—H24E109.5
H14D—C143—H14E109.5H24D—C243—H24E109.5
N141—C143—H14F109.5N241—C243—H24F109.5
H14D—C143—H14F109.5H24D—C243—H24F109.5
H14E—C143—H14F109.5H24E—C243—H24F109.5
C116—C115—C114120.93 (14)C216—C215—C214121.27 (15)
C116—C115—H115119.5C216—C215—H215119.4
C114—C115—H115119.5C214—C215—H215119.4
C115—C116—C111122.56 (15)C215—C216—C211122.00 (15)
C115—C116—H116118.7C215—C216—H216119.0
C111—C116—H116118.7C211—C216—H216119.0
C17a—O11—C12—O1310.49 (16)C27a—O21—C22—O2315.0 (2)
O11—C12—O13—C13a10.87 (16)O21—C22—O23—C23a14.25 (19)
C12—O13—C13a—C14172.57 (15)C22—O23—C23a—C24173.88 (18)
C12—O13—C13a—C17a7.06 (16)C22—O23—C23a—C27a7.96 (19)
O13—C13a—C14—C15179.27 (13)O23—C23a—C24—C25179.64 (15)
C17a—C13a—C14—C151.1 (2)C27a—C23a—C24—C251.7 (2)
C13a—C14—C15—N15179.51 (13)C23a—C24—C25—N25179.44 (14)
C13a—C14—C15—C160.7 (2)C23a—C24—C25—C261.3 (2)
N15—C15—C16—C17178.75 (13)N25—C25—C26—C27179.29 (14)
C14—C15—C16—C170.0 (2)C24—C25—C26—C270.0 (2)
N15—C15—C16—C180.8 (2)N25—C25—C26—C282.9 (2)
C14—C15—C16—C18179.59 (12)C24—C25—C26—C28177.80 (13)
C15—C16—C17—C17a0.3 (2)C25—C26—C27—C27a0.8 (2)
C18—C16—C17—C17a179.87 (13)C28—C26—C27—C27a176.94 (14)
C16—C17—C17a—O11179.73 (13)C26—C27—C27a—O21177.74 (16)
C16—C17—C17a—C13a0.1 (2)C26—C27—C27a—C23a0.5 (2)
C12—O11—C17a—C17173.72 (15)C22—O21—C27a—C27172.35 (18)
C12—O11—C17a—C13a6.16 (17)C22—O21—C27a—C23a10.1 (2)
C14—C13a—C17a—C170.9 (2)C24—C23a—C27a—C270.9 (3)
O13—C13a—C17a—C17179.46 (13)O23—C23a—C27a—C27179.13 (15)
C14—C13a—C17a—O11179.00 (13)C24—C23a—C27a—O21176.90 (15)
O13—C13a—C17a—O110.65 (17)O23—C23a—C27a—O211.4 (2)
C15—C16—C18—O183.5 (2)C27—C26—C28—O28171.91 (13)
C17—C16—C18—O18176.13 (12)C25—C26—C28—O285.8 (2)
C15—C16—C18—C19174.87 (13)C27—C26—C28—C297.5 (2)
C17—C16—C18—C195.5 (2)C25—C26—C28—C29174.76 (13)
O18—C18—C19—C1109.5 (2)O28—C28—C29—C2105.2 (2)
C16—C18—C19—C110168.85 (13)C26—C28—C29—C210174.21 (13)
C18—C19—C110—C111174.54 (14)C28—C29—C210—C211179.30 (13)
C19—C110—C111—C1128.8 (2)C29—C210—C211—C216177.31 (15)
C19—C110—C111—C116171.81 (14)C29—C210—C211—C2120.1 (2)
C116—C111—C112—C1130.3 (2)C216—C211—C212—C2130.5 (2)
C110—C111—C112—C113179.75 (14)C210—C211—C212—C213176.81 (14)
C111—C112—C113—C1140.6 (2)C211—C212—C213—C2140.9 (2)
C112—C113—C114—N141178.03 (13)C212—C213—C214—N241179.60 (16)
C112—C113—C114—C1150.7 (2)C212—C213—C214—C2150.5 (2)
C115—C114—N141—C1434.4 (2)C215—C214—N241—C242173.59 (18)
C113—C114—N141—C143176.93 (13)C213—C214—N241—C2426.3 (3)
C115—C114—N141—C142168.98 (14)C215—C214—N241—C2437.1 (3)
C113—C114—N141—C14212.4 (2)C213—C214—N241—C243173.01 (17)
N141—C114—C115—C116178.19 (14)N241—C214—C215—C216179.69 (17)
C113—C114—C115—C1160.5 (2)C213—C214—C215—C2160.2 (3)
C114—C115—C116—C1110.3 (2)C214—C215—C216—C2110.6 (3)
C112—C111—C116—C1150.1 (2)C212—C211—C216—C2150.3 (2)
C110—C111—C116—C115179.61 (14)C210—C211—C216—C215177.64 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H15A···O180.882.032.6433 (14)125
N15—H15B···O28i0.882.263.0867 (13)157
N25—H25A···O280.881.942.6237 (17)133
N25—H25B···O180.882.203.0606 (17)165
C14—H14···O28i0.952.383.2067 (18)145
C24—H24···O180.952.523.3212 (19)142
C212—H212···O13ii0.952.603.4508 (18)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC19H19NO6C18H18N2O3
Mr357.35310.34
Crystal system, space groupMonoclinic, P21/cTriclinic, P1
Temperature (K)150150
a, b, c (Å)23.5477 (4), 4.9605 (1), 14.2556 (8)9.5849 (2), 12.3218 (4), 13.3304 (4)
α, β, γ (°)90, 100.702 (1), 9083.4617 (14), 80.2411 (17), 85.7271 (16)
V3)1636.21 (10)1539.04 (8)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.110.09
Crystal size (mm)0.4 × 0.1 × 0.10.22 × 0.14 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
Tmin, Tmax0.958, 0.9890.980, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
11152, 3622, 2832 23078, 6884, 4873
Rint0.0480.085
(sin θ/λ)max1)0.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.124, 1.03 0.054, 0.154, 1.02
No. of reflections36226884
No. of parameters238419
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.320.30, 0.34

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O80.882.012.651 (2)129
C16—H16···O1i0.952.513.398 (2)155
Symmetry code: (i) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N15—H15A···O180.882.032.6433 (14)125
N15—H15B···O28i0.882.263.0867 (13)157
N25—H25A···O280.881.942.6237 (17)133
N25—H25B···O180.882.203.0606 (17)165
C14—H14···O28i0.952.383.2067 (18)145
C24—H24···O180.952.523.3212 (19)142
C212—H212···O13ii0.952.603.4508 (18)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z1.
 

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