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In the crystal structure of 2-acetamido-N-benz­yl-2-(methoxy­amino)acetamide (3L), C12H17N3O3, the 2-acetyl­amino­acetamide moiety has a linearly extended conformation, with an inter­planar angle between the two amide groups of 157.3 (1)°. In 2-acetamido-N-benz­yl-2-[meth­oxy(meth­yl)­amino]­acetamide (3N), C13H19N3O3, the planes of the two amide groups inter­sect at an angle of 126.4 (4)°, resulting in a chain that is slightly more bent. The replacement of the methoxy­amino H atom of 3L with a methyl group to form 3N and concomitant loss of hydrogen bonding results in some positional/thermal disorder in the meth­oxy­(methyl)­amino group. In both structures, in addition to classical N—H...O hydrogen bonds, there are also weak non-standard C—H...O hydrogen bonds. The hydrogen bonds and packing inter­actions result in planar hydro­philic and hydro­phobic areas perpendicular to the c axis in 3L and parallel to the ab plane in the N-meth­yl derivative. Stereochemical comparisons with phenytoin have identified two O atoms and a phenyl group as mol­ecular features likely to be responsible for the anticon­vulsant activities of these compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105014745/fg1843sup1.cif
Contains datablocks 3L, 3N, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105014745/fg18433Lsup2.hkl
Contains datablock 3L

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105014745/fg18433Nsup3.hkl
Contains datablock 3N

CCDC references: 278553; 278554

Comment top

The title compounds, 2-(acetylamino)-N-benzyl-2-(methoxyamino)acetamide (3L), and its N-methyl derivative (3N), are members of a series of functionalized α-heteroatom-substituted non-naturally occurring amino acids synthesized and tested for anticonvulsant activity (Kohn et al., 1991). These two were the most potent of the group, demonstrating median effective dose values required to prevent maximal electroshock seizures in mice comparable to the well known antiepileptic drug phenytoin. We determined the crystal structures of 3L and 3N in order to investigate the stereochemical basis for their anticonvulsant properties.

The structure of 3L is presented in Fig. 1. The asymmetric unit contains one molecule with atoms C7–C13 extended linearly, and with the two amide group planes (atoms C7/N8/C9/C10/O14 and C10/N11/C12/C13/O18) intersecting at an angle of 157.3 (1)°. The C9—C10—N11—C12 torsion angle is −160.9 (2)°. The sp3-hybridization of N15 is indicated by the sum of the bond angles at N15 of 319.4°. Four standard hydrogen bonds, weak non-standard C—H···O hydrogen bonds (Table 1) and van der Waals interactions are the main contributors to the crystal packing. The molecules are packed in head-to-head and tail-to-tail fashion, creating distinct hydrophilic and hydrophobic regions running perpendicular to the c axis, as shown in Fig. 2. The 3N chain conformation (Fig. 3) is a little more curved, with an angle of 126.4 (4)° between the two planar amide groups (atoms C7/N8/C9/C10/O14 and C10/N11/C12/C13/O18). The C9—C10—N11—C12 torsion angle is −128.5 (10)°. The replacement of the H atom at N15 in 3L with the methyl group in 3N results in a much weaker hydrogen-bonding scheme, with only two classical N—H···O interactions producing infinite molecular chains parallel to the a axis (see Table 2). Van der Waals forces and non-standard hydrogen bonds also contribute to the crystal packing, creating planar hydrophillic and hydrophobic areas parallel to the ab plane. The weaker hydrogen-bonding interactions are very probably responsible for abnormal displacement ellipsoids and mild disorder in the N15, O16, C17 and C18 positions, as well as high displacement parameters for some other atoms.. Despite these problems, the overall conformational structure of the molecules in the solid state is undoubtedly established.

We have compared the structures of 3L (Fig. 4) and 3N (Fig. 5) with that of phenytoin (Camerman & Camerman, 1971) a chemically different clinically used anticonvulsant, in order to correlate pharmacological properties with stereochemical features. The structures were superposed by maximizing the fit of three atoms in each, viz. O14, O16 and C6 in 3L, and O14, O16 and C5 in 3N, with the two carbonyl O atoms and atom C15 (for 3L) or C19 (for 3N) in phenytoin. Atom O16 was chosen, rather than the second carbonyl O atom in 3L and 3N, because the pharmacological evaluations had shown that a functionalized O atom located two atoms removed from the Cα atom was necessary for maximal activity in the series tested (Kohn et al., 1991). To yield better phenyl-group fits, rotations of 80° about C7—N8 and 90° about C6—C7 were performed for 3L, and a single rotation of 65° about C6—C7 was performed for 3N. The superpositions show that the O atoms in each molecule can occupy similar positions in space (small movements of the methoxy O atoms in 3L and 3N, via C10—N15 bond rotation, would make the correspondences exact), and the hydrophobic phenyl groups can also occupy similar regions. Since these are the stereochemical determinants of phenytoin anticonvulsant activity (Camerman & Camerman, 1981), the results are indicative that the similar activity of these compounds could be mediated through mechanisms similar to those of phenytoin.

Experimental top

Compounds 3N and 3L were supplied by Dr H. Kohn (Kohn et al., 1991). After extensive crystallization experiments, crystals of 3L were obtained by slow evaporation from a 1:1 benzene–chloroform solution at 278 K. The crystals took the form of small colorless needles, generally of low quality. Crystals of 3N were obtained by slow evaporation from a 1:1 chloroform–toluene mixture, and were of poor quality. Additional crystallization trials to produce better crystals were unsuccessful.

Refinement top

All H atoms for both compounds could be located in difference maps and were subsequently allowed for as riding atoms, except for atom H15 on N15 in 3L. For 3L, one overall isotropic displacement parameter was refined for methyl H atoms and another for the rest [Uiso(H) = 0.116 (7) and 0.079 (4) Å2, respectively]. For 3N, the corresponding values are 0.123 (16) and 0.099 (15) Å2. The range of C—H distances is 0.93–0.98 Å, and the amide N—H distances are 0.86 Å. The N15—H15 bond length in 3L is 0.90 (3) Å.

Computing details top

For both compounds, data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: DATRDN The X-ray System (Stewart, 1976); 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: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of 3L, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A stereodiagram of the molecular packing and hydrogen-bond scheme in 3L. Atoms are drawn as circles of arbitrary radii.
[Figure 3] Fig. 3. The molecular structure of 3N, showing 50% probability displacement ellipsoids.
[Figure 4] Fig. 4. Superposition of 3L and phenytoin (large circles, solid bonds).
[Figure 5] Fig. 5. Superposition of 3 N and phenytoin (large circles, solid bonds).
(3L) 2-acetamido-N-benzyl-2-(methoxyamino)acetamide top
Crystal data top
C12H17N3O3Dx = 1.279 Mg m3
Mr = 251.29Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcnCell parameters from 3 reflections
a = 17.998 (5) Åθ = 19–44°
b = 7.112 (3) ŵ = 0.77 mm1
c = 20.390 (6) ÅT = 294 K
V = 2610.0 (15) Å3Needle, colorless
Z = 80.47 × 0.11 × 0.07 mm
F(000) = 1072
Data collection top
Picker FACS-1 4-circle
diffractometer
1655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Ni filtered radiation monochromatorθmax = 65.0°, θmin = 4.3°
θ/2θ scanh = 021
Absorption correction: ψ scan
(North et al., 1968)
k = 08
Tmin = 0.900, Tmax = 0.944l = 023
2225 measured reflections3 standard reflections every 100 reflections
2225 independent reflections intensity decay: 1.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0284P)2 + 2.7803P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2225 reflectionsΔρmax = 0.21 e Å3
172 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0045 (3)
Crystal data top
C12H17N3O3V = 2610.0 (15) Å3
Mr = 251.29Z = 8
Orthorhombic, PbcnCu Kα radiation
a = 17.998 (5) ŵ = 0.77 mm1
b = 7.112 (3) ÅT = 294 K
c = 20.390 (6) Å0.47 × 0.11 × 0.07 mm
Data collection top
Picker FACS-1 4-circle
diffractometer
1655 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.000
Tmin = 0.900, Tmax = 0.9443 standard reflections every 100 reflections
2225 measured reflections intensity decay: 1.9%
2225 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.21 e Å3
2225 reflectionsΔρmin = 0.16 e Å3
172 parameters
Special details top

Experimental. PICKER FACS-1 mechanical limit does not allow for data collection above θ = 65°

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
C10.39659 (17)0.2949 (5)0.28393 (17)0.0605 (9)
H10.43640.36970.29690.079 (4)*
C20.3922 (2)0.2338 (6)0.21977 (19)0.0764 (11)
H20.42920.26630.19000.079 (4)*
C30.3335 (2)0.1255 (6)0.20012 (19)0.0816 (12)
H30.33020.08440.15690.079 (4)*
C40.2797 (2)0.0783 (6)0.24416 (19)0.0874 (13)
H40.23980.00430.23090.079 (4)*
C50.28391 (18)0.1390 (5)0.30809 (17)0.0673 (10)
H50.24650.10690.33750.079 (4)*
C60.34280 (15)0.2466 (4)0.32902 (15)0.0495 (7)
C70.35048 (16)0.3025 (4)0.39990 (15)0.0516 (8)
H7A0.37770.41990.40300.079 (4)*
H7B0.30160.32160.41880.079 (4)*
N80.38966 (12)0.1566 (3)0.43638 (11)0.0461 (6)
H80.43740.16050.43740.079 (4)*
C90.35566 (14)0.0184 (4)0.46798 (14)0.0432 (7)
C100.40705 (14)0.1385 (4)0.49143 (14)0.0430 (7)
H100.43630.08780.52790.079 (4)*
N110.36400 (12)0.2936 (3)0.51716 (11)0.0443 (6)
H110.31780.30460.50700.079 (4)*
C120.39605 (16)0.4203 (4)0.55683 (13)0.0466 (7)
C130.34744 (17)0.5738 (5)0.58287 (16)0.0600 (9)
H13A0.29980.56820.56180.116 (7)*
H13B0.34130.55820.62930.116 (7)*
H13C0.37010.69350.57420.116 (7)*
O140.28907 (9)0.0156 (3)0.48015 (11)0.0597 (6)
N150.45887 (13)0.1862 (4)0.43943 (12)0.0494 (6)
H150.4853 (18)0.289 (5)0.4504 (16)0.068 (11)*
O160.41345 (12)0.2489 (3)0.38547 (10)0.0578 (6)
C170.4510 (2)0.2061 (6)0.32599 (18)0.0830 (12)
H17A0.41930.23490.28950.116 (7)*
H17B0.49560.27970.32310.116 (7)*
H17C0.46350.07490.32520.116 (7)*
O180.46243 (11)0.4082 (3)0.57164 (10)0.0600 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0405 (16)0.069 (2)0.072 (2)0.0016 (16)0.0018 (15)0.0105 (18)
C20.059 (2)0.099 (3)0.071 (2)0.005 (2)0.0106 (18)0.016 (2)
C30.095 (3)0.095 (3)0.055 (2)0.007 (3)0.009 (2)0.009 (2)
C40.093 (3)0.097 (3)0.072 (2)0.040 (2)0.019 (2)0.019 (2)
C50.062 (2)0.078 (2)0.062 (2)0.0233 (19)0.0049 (17)0.0175 (19)
C60.0416 (15)0.0457 (17)0.0611 (18)0.0019 (13)0.0035 (14)0.0141 (14)
C70.0506 (17)0.0406 (16)0.0635 (19)0.0035 (14)0.0007 (14)0.0070 (14)
N80.0341 (12)0.0480 (14)0.0562 (14)0.0027 (11)0.0002 (10)0.0073 (12)
C90.0325 (13)0.0469 (16)0.0501 (16)0.0016 (12)0.0047 (12)0.0031 (14)
C100.0334 (13)0.0479 (16)0.0478 (16)0.0019 (12)0.0013 (12)0.0024 (13)
N110.0356 (12)0.0490 (14)0.0482 (13)0.0012 (10)0.0019 (10)0.0066 (11)
C120.0442 (15)0.0529 (17)0.0427 (16)0.0052 (14)0.0033 (13)0.0037 (14)
C130.0604 (19)0.059 (2)0.0608 (19)0.0035 (16)0.0046 (16)0.0136 (17)
O140.0333 (10)0.0542 (13)0.0915 (17)0.0017 (10)0.0047 (10)0.0090 (12)
N150.0366 (13)0.0538 (16)0.0579 (15)0.0041 (12)0.0031 (12)0.0056 (13)
O160.0621 (13)0.0578 (13)0.0536 (12)0.0020 (11)0.0050 (10)0.0008 (11)
C170.114 (3)0.077 (3)0.058 (2)0.007 (2)0.026 (2)0.0061 (19)
O180.0419 (11)0.0746 (15)0.0634 (13)0.0049 (11)0.0058 (10)0.0150 (12)
Geometric parameters (Å, º) top
C1—C61.379 (4)C9—C101.527 (4)
C1—C21.381 (5)C10—N111.446 (3)
C1—H10.93C10—N151.452 (3)
C2—C31.368 (5)C10—H100.98
C2—H20.93N11—C121.341 (3)
C3—C41.362 (5)N11—H110.86
C3—H30.93C12—O181.235 (3)
C4—C51.375 (5)C12—C131.496 (4)
C4—H40.93C13—H13A0.96
C5—C61.375 (4)C13—H13B0.96
C5—H50.93C13—H13C0.96
C6—C71.505 (4)N15—O161.442 (3)
C7—N81.458 (4)N15—H150.90 (3)
C7—H7A0.97O16—C171.421 (4)
C7—H7B0.97C17—H17A0.96
N8—C91.325 (3)C17—H17B0.96
N8—H80.86C17—H17C0.96
C9—O141.224 (3)
C6—C1—C2120.9 (3)N8—C9—C10114.5 (2)
C6—C1—H1119.5N11—C10—N15115.5 (2)
C2—C1—H1119.5N11—C10—C9110.3 (2)
C3—C2—C1119.9 (3)N15—C10—C9109.3 (2)
C3—C2—H2120.1N11—C10—H10107.1
C1—C2—H2120.1N15—C10—H10107.1
C4—C3—C2119.7 (4)C9—C10—H10107.1
C4—C3—H3120.2C12—N11—C10120.0 (2)
C2—C3—H3120.2C12—N11—H11120.0
C3—C4—C5120.6 (4)C10—N11—H11120.0
C3—C4—H4119.7O18—C12—N11121.1 (3)
C5—C4—H4119.7O18—C12—C13122.0 (3)
C6—C5—C4120.7 (3)N11—C12—C13116.9 (3)
C6—C5—H5119.6C12—C13—H13A109.5
C4—C5—H5119.6C12—C13—H13B109.5
C5—C6—C1118.2 (3)H13A—C13—H13B109.5
C5—C6—C7121.0 (3)C12—C13—H13C109.5
C1—C6—C7120.7 (3)H13A—C13—H13C109.5
N8—C7—C6110.3 (2)H13B—C13—H13C109.5
N8—C7—H7A109.6O16—N15—C10105.4 (2)
C6—C7—H7A109.6O16—N15—H15104 (2)
N8—C7—H7B109.6C10—N15—H15110 (2)
C6—C7—H7B109.6C17—O16—N15108.4 (2)
H7A—C7—H7B108.1O16—C17—H17A109.5
C9—N8—C7123.5 (2)O16—C17—H17B109.5
C9—N8—H8118.2H17A—C17—H17B109.5
C7—N8—H8118.2O16—C17—H17C109.5
O14—C9—N8124.3 (3)H17A—C17—H17C109.5
O14—C9—C10121.2 (3)H17B—C17—H17C109.5
C6—C1—C2—C30.7 (6)C7—N8—C9—C10168.7 (2)
C1—C2—C3—C40.2 (6)O14—C9—C10—N1110.1 (4)
C2—C3—C4—C50.2 (7)N8—C9—C10—N11172.2 (2)
C3—C4—C5—C60.8 (6)O14—C9—C10—N15138.2 (3)
C4—C5—C6—C11.3 (5)N8—C9—C10—N1544.1 (3)
C4—C5—C6—C7175.8 (3)N15—C10—N11—C1274.5 (3)
C2—C1—C6—C51.3 (5)C9—C10—N11—C12160.9 (2)
C2—C1—C6—C7175.8 (3)C10—N11—C12—O180.6 (4)
C5—C6—C7—N886.9 (4)C10—N11—C12—C13178.4 (3)
C1—C6—C7—N890.1 (3)N11—C10—N15—O1664.3 (3)
C6—C7—N8—C992.7 (3)C9—C10—N15—O1660.8 (3)
C7—N8—C9—O1413.7 (5)C10—N15—O16—C17150.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O18i0.862.533.212 (3)137
N11—H11···O140.862.402.687 (3)100
N11—H11···O14ii0.862.373.163 (3)153
N15—H15···O18iii0.90 (3)2.39 (3)3.221 (4)153 (3)
C7—H7A···O16iv0.972.473.399 (4)161
C7—H7B···O14v0.972.483.359 (4)151
C13—H13A···O14ii0.962.383.290 (4)157
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y1/2, z; (iii) x+1, y1, z+1; (iv) x, y+1, z; (v) x+1/2, y+1/2, z.
(3N) 2-acetamido-N-benzyl-2-[methoxy(methyl)amino]acetamide top
Crystal data top
C13H19N3O3Z = 2
Mr = 265.31F(000) = 284
Triclinic, P1Dx = 1.244 Mg m3
a = 4.859 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.587 (3) ÅCell parameters from 32 reflections
c = 14.168 (4) Åθ = 23–45°
α = 86.84 (2)°µ = 0.74 mm1
β = 80.66 (3)°T = 294 K
γ = 80.28 (3)°Needle, colorless
V = 708.6 (4) Å30.42 × 0.09 × 0.08 mm
Data collection top
Picker FACS-1 4-circle
diffractometer
737 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.085
Ni-filtered radiation monochromatorθmax = 45.0°, θmin = 3.2°
θ/2θ scanh = 40
Absorption correction: ψ scan
(North et al., 1968)
k = 99
Tmin = 0.930, Tmax = 0.934l = 1212
1338 measured reflections3 standard reflections every 100 reflections
1145 independent reflections intensity decay: 2.7%
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)] = 0.102Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0768P)2 + 2.5323P]
where P = (Fo2 + 2Fc2)/3
1145 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.53 e Å3
25 restraintsΔρmin = 0.30 e Å3
Crystal data top
C13H19N3O3γ = 80.28 (3)°
Mr = 265.31V = 708.6 (4) Å3
Triclinic, P1Z = 2
a = 4.859 (2) ÅCu Kα radiation
b = 10.587 (3) ŵ = 0.74 mm1
c = 14.168 (4) ÅT = 294 K
α = 86.84 (2)°0.42 × 0.09 × 0.08 mm
β = 80.66 (3)°
Data collection top
Picker FACS-1 4-circle
diffractometer
737 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.085
Tmin = 0.930, Tmax = 0.934θmax = 45.0°
1338 measured reflections3 standard reflections every 100 reflections
1145 independent reflections intensity decay: 2.7%
Refinement top
R[F2 > 2σ(F2)] = 0.10225 restraints
wR(F2) = 0.250H-atom parameters constrained
S = 1.12Δρmax = 0.53 e Å3
1145 reflectionsΔρmin = 0.30 e Å3
174 parameters
Special details top

Experimental. The crystal was small and of poor quality and no reflections were observable beyond theta of 45°.

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.

Refinement of 3 N indicated N15 could be split into two positions; doing so reduced R to 0.082 but resulted in non-positive definite temperature factors and poor interatomic distances for the lower occupancy position.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O140.1023 (14)0.7475 (8)0.6884 (5)0.078 (3)
O160.4177 (18)0.5637 (11)0.8374 (7)0.133 (4)
O180.6410 (13)0.9777 (7)0.8618 (5)0.070 (3)
N80.5635 (16)0.7245 (8)0.6334 (7)0.065 (3)
H80.73080.72760.64470.099 (15)*
N110.2602 (15)0.8993 (8)0.8302 (6)0.048 (2)
H110.08080.91520.82980.099 (15)*
N150.291 (3)0.6784 (9)0.8729 (7)0.108 (4)
C10.926 (2)0.6332 (12)0.4065 (8)0.069 (3)
H10.89790.54840.41600.099 (15)*
C21.130 (2)0.6657 (14)0.3362 (9)0.088 (4)
H21.23670.60170.29720.099 (15)*
C31.182 (3)0.7847 (17)0.3213 (10)0.099 (5)
H31.32640.80190.27330.099 (15)*
C41.023 (3)0.8832 (14)0.3762 (11)0.099 (4)
H41.05490.96720.36480.099 (15)*
C50.810 (2)0.8522 (13)0.4497 (10)0.085 (4)
H50.70380.91550.48950.099 (15)*
C60.763 (2)0.7271 (12)0.4627 (8)0.059 (3)
C70.530 (2)0.6909 (13)0.5390 (9)0.081 (4)
H7A0.53100.59930.53810.099 (15)*
H7B0.34900.73430.52460.099 (15)*
C90.346 (2)0.7519 (9)0.7046 (8)0.045 (3)
C100.4154 (19)0.7731 (10)0.8004 (8)0.057 (3)
H100.61940.76690.79930.099 (15)*
C120.383 (2)0.9883 (10)0.8597 (7)0.051 (3)
C130.194 (2)1.1100 (10)0.8933 (9)0.077 (4)
H13A0.24831.18130.85410.123 (16)*
H13B0.00191.10310.88840.123 (16)*
H13C0.20811.12310.95870.123 (16)*
C170.178 (2)0.4949 (13)0.8391 (10)0.108 (5)
H17A0.04040.54240.80350.123 (16)*
H17B0.25160.41390.80990.123 (16)*
H17C0.09020.48060.90370.123 (16)*
C180.439 (3)0.6849 (12)0.9572 (9)0.095 (4)
H18A0.63750.68150.93420.123 (16)*
H18B0.36620.76410.98900.123 (16)*
H18C0.41230.61431.00130.123 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O140.017 (4)0.142 (8)0.075 (6)0.011 (4)0.006 (4)0.022 (5)
O160.076 (7)0.175 (11)0.130 (9)0.010 (7)0.004 (6)0.023 (8)
O180.015 (4)0.080 (6)0.116 (7)0.012 (4)0.003 (4)0.020 (5)
N80.022 (5)0.109 (8)0.063 (7)0.010 (5)0.004 (5)0.030 (6)
N110.017 (4)0.041 (6)0.081 (7)0.001 (5)0.000 (4)0.004 (5)
N150.211 (13)0.033 (6)0.048 (6)0.071 (7)0.015 (6)0.004 (5)
C10.051 (7)0.081 (8)0.071 (8)0.020 (6)0.004 (5)0.000 (6)
C20.061 (8)0.126 (10)0.073 (9)0.026 (8)0.017 (6)0.010 (9)
C30.084 (10)0.146 (12)0.075 (10)0.055 (9)0.001 (7)0.012 (9)
C40.094 (11)0.083 (9)0.126 (13)0.029 (8)0.037 (8)0.043 (8)
C50.056 (7)0.077 (7)0.119 (11)0.004 (6)0.012 (6)0.006 (8)
C60.033 (6)0.077 (7)0.068 (8)0.009 (5)0.011 (5)0.007 (6)
C70.039 (7)0.127 (11)0.076 (10)0.021 (7)0.003 (5)0.012 (8)
C90.037 (7)0.039 (7)0.058 (6)0.005 (5)0.005 (6)0.004 (5)
C100.029 (6)0.074 (9)0.067 (7)0.004 (6)0.018 (6)0.013 (6)
C120.051 (8)0.046 (7)0.054 (8)0.014 (6)0.005 (6)0.003 (6)
C130.061 (7)0.043 (7)0.127 (11)0.004 (5)0.013 (7)0.015 (7)
C170.052 (8)0.131 (13)0.147 (14)0.051 (8)0.008 (8)0.015 (10)
C180.120 (11)0.077 (10)0.084 (9)0.020 (8)0.008 (8)0.016 (8)
Geometric parameters (Å, º) top
O14—C91.251 (11)C4—H40.93
O16—N151.350 (11)C5—C61.379 (15)
O16—C171.472 (12)C5—H50.93
O18—C121.242 (12)C6—C71.516 (14)
N8—C91.343 (11)C7—H7A0.9701
N8—C71.443 (13)C7—H7B0.97
N8—H80.86C9—C101.487 (14)
N11—C121.318 (12)C10—H100.98
N11—C101.467 (12)C12—O181.242 (11)
N11—H110.86C12—C131.504 (14)
N15—C181.502 (13)C13—H13A0.9601
N15—C101.521 (12)C13—H13B0.96
C1—C61.367 (14)C13—H13C0.96
C1—C21.359 (15)C17—H17A0.96
C1—H10.9299C17—H17B0.96
C2—C31.325 (17)C17—H17C0.96
C2—H20.9299C18—H18A0.96
C3—C41.381 (18)C18—H18B0.96
C3—H30.9301C18—H18C0.9601
C4—C51.410 (17)
N15—O16—C17102.7 (10)H7A—C7—H7B107.9
C9—N8—C7123.4 (8)O14—C9—N8118.3 (9)
C9—N8—H8118.1O14—C9—C10124.3 (9)
C7—N8—H8118.5N8—C9—C10117.1 (9)
C12—N11—C10122.6 (8)N11—C10—C9106.7 (8)
C12—N11—H11118.6N11—C10—N15104.9 (8)
C10—N11—H11118.7C9—C10—N15109.2 (9)
O16—N15—C18101.4 (9)N11—C10—H10112.2
O16—N15—C10103.0 (9)C9—C10—H10112.0
C18—N15—C10103.5 (10)N15—C10—H10111.5
C6—C1—C2118.9 (12)O18—C12—N11124.7 (9)
C6—C1—H1120.6O18—C12—N11124.7 (9)
C2—C1—H1120.5O18—C12—C13118.9 (11)
C3—C2—C1122.7 (14)O18—C12—C13118.9 (11)
C3—C2—H2118.8N11—C12—C13116.4 (10)
C1—C2—H2118.5C12—C13—H13A109.8
C2—C3—C4120.7 (14)C12—C13—H13B109.1
C2—C3—H3119.5H13A—C13—H13B109.5
C4—C3—H3119.7C12—C13—H13C109.6
C3—C4—C5117.8 (13)H13A—C13—H13C109.5
C3—C4—H4121.1H13B—C13—H13C109.5
C5—C4—H4121.0O16—C17—H17A110.6
C6—C5—C4119.5 (12)O16—C17—H17B107.1
C6—C5—H5120.2H17A—C17—H17B109.5
C4—C5—H5120.2O16—C17—H17C110.7
C1—C6—C5120.3 (11)H17A—C17—H17C109.5
C1—C6—C7118.7 (11)H17B—C17—H17C109.5
C5—C6—C7121.0 (11)N15—C18—H18A108.4
N8—C7—C6112.2 (9)N15—C18—H18B109.4
N8—C7—H7A109.1H18A—C18—H18B109.5
C6—C7—H7A109.2N15—C18—H18C110.7
N8—C7—H7B109.2H18A—C18—H18C109.5
C6—C7—H7B109.2H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O14i0.862.052.901 (10)172
N11—H11···O18ii0.862.112.950 (9)165
C10—H10···O14i0.982.593.428 (11)144
C10—H10···O180.982.472.823 (12)101
C13—H13B···O18ii0.962.463.331 (12)151
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

(3L)(3N)
Crystal data
Chemical formulaC12H17N3O3C13H19N3O3
Mr251.29265.31
Crystal system, space groupOrthorhombic, PbcnTriclinic, P1
Temperature (K)294294
a, b, c (Å)17.998 (5), 7.112 (3), 20.390 (6)4.859 (2), 10.587 (3), 14.168 (4)
α, β, γ (°)90, 90, 9086.84 (2), 80.66 (3), 80.28 (3)
V3)2610.0 (15)708.6 (4)
Z82
Radiation typeCu KαCu Kα
µ (mm1)0.770.74
Crystal size (mm)0.47 × 0.11 × 0.070.42 × 0.09 × 0.08
Data collection
DiffractometerPicker FACS-1 4-circle
diffractometer
Picker FACS-1 4-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
ψ scan
(North et al., 1968)
Tmin, Tmax0.900, 0.9440.930, 0.934
No. of measured, independent and
observed [I > 2σ(I)] reflections
2225, 2225, 1655 1338, 1145, 737
Rint0.0000.085
θmax (°)65.045.0
(sin θ/λ)max1)0.5880.458
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.146, 1.00 0.102, 0.250, 1.12
No. of reflections22251145
No. of parameters172174
No. of restraints025
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.160.53, 0.30

Computer programs: Picker Operating Manual (Picker, 1967), Picker Operating Manual, DATRDN The X-ray System (Stewart, 1976), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) for (3L) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O18i0.862.533.212 (3)137
N11—H11···O140.862.402.687 (3)100
N11—H11···O14ii0.862.373.163 (3)153
N15—H15···O18iii0.90 (3)2.39 (3)3.221 (4)153 (3)
C7—H7A···O16iv0.972.473.399 (4)161
C7—H7B···O14v0.972.483.359 (4)151
C13—H13A···O14ii0.962.383.290 (4)157
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y1/2, z; (iii) x+1, y1, z+1; (iv) x, y+1, z; (v) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) for (3N) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O14i0.862.052.901 (10)172
N11—H11···O18ii0.862.112.950 (9)165
C10—H10···O14i0.982.593.428 (11)144
C10—H10···O180.982.472.823 (12)101
C13—H13B···O18ii0.962.463.331 (12)151
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

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