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In the title compound, C23H22N4O, there is evidence for some bond fixation in the aryl component of the quinolinone unit. Pairs of mol­ecules related by inversion are linked into R22(8) dimers by almost linear N-H...O hydrogen bonds, and dimers related by inversion are linked into chains by a single aromatic [pi]-[pi] stacking inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109033861/sk3342sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109033861/sk3342Isup2.hkl
Contains datablock I

CCDC reference: 756002

Comment top

We report here the structure of the title compound, (I) (Fig. 1). It is related to a series of 5-benzylamino-3-tert-butyl-1-phenyl-1H-pyrazoles, the structures of which were reported recently (Castillo et al., 2009), but differs from the earlier series in the nature of its arylidene moiety, the bicyclic heterocyclic fragment quinolin-2(1H)-one-3-yl, where the N—H and CO groups play the leading role in the supramolecular aggregation.

Although the C—C distances in the pendent aryl ring (C11–C16) span only a small range, 1.380 (2)–1.392 (2) Å, the C—C distances in the aryl component of the quinolinone unit show much wider variation (Table 1). In particular, the C65—C66 and C67—C68 distances (cf. Fig. 1) are significantly shorter than the other distances in this ring, suggesting some bond fixation analogous to that found in naphthalenes, so that the forms (I) and (Ia) (see scheme [No resonance forms shown - please provide revision]) are probably both significant contributors to the overall electronic structure.

The tert-butyl substituent of (I) is oriented relative to the pyrazole ring such that one of the methyl C atoms, C32, is close to but displaced from the plane of the pyrazole ring, so that the tert-butylpyrazole fragment has only approximate local mirror symmetry. In effect (Table 1), the tert-butyl group has rotated by ca 6° about the C3—C31 bond away from the mirror-symmetry conformation. On the other hand, the C11–C16 phenyl group makes a dihedral angle of 21.9 (2)° with the pyrazole ring. There is a short intramolecular C—H···N contact involving atom C12 (Table 2), but the dihedral angle makes it possible that this is actually a repulsive rather than an attractive contact. Apart from the tert-butyl and phenyl substituents, the rest of the molecular skeleton is nearly planar, as indicated by the leading torsion angles (Table 1).

The supramolecular aggregation of (I) is dominated by a fairly short and almost linear N—H···O hydrogen bond (Table 2). Pairs of these hydrogen bonds link molecules related by inversion into R22(8) (Bernstein et al., 1995) dimers, with the reference dimer centred at (0, 1/2, 1/2). A single aromatic ππ stacking interaction links the hydrogen-bonded dimers into a chain. The C11–C16 phenyl rings in the molecules at (x, y, z) and (2 - x, 1 - y, 2 - z) are strictly parallel, with an interplanar spacing of 3.484 (2) Å; the corresponding ring-centroid separation is 3.871 (2) Å, with a ring-centroid offset of 1.687 (2) Å. The two molecules involved form parts of hydrogen-bonded dimers centred at (0, 1/2, 1/2) and (2, 1/2, 3/2), respectively, and propagation by inversion of the hydrogen bond and the ππ stacking interaction generates a chain of π-stacked hydrogen-bonded dimers running parallel to the [201] direction (Fig. 2). Within this chain, R22(8) rings centred at (2n, 1/2, n + 1/2), where n represents an integer, alternate with ππ stacking interactions across (2n + 1, 1/2, n + 1), where n again represents an integer (Fig. 2). There are no direction-specific interactions between the chains. In particular, C—H···π(arene) hydrogen bonds are absent.

Almost all of the quinolin-2-ones with the same substituent pattern as in (I) for which structures are recorded in the Cambridge Structural Database (CSD, Version?; Allen, 2002) carry other substituents with potential hydrogen-bonding capacity, particularly hydroxyl, amino and carbonyl groups. However, two compounds of this type, namely (II) (CSD refcode ABABEL; Li et al., 2004) and (III) (CSD refcode XAWHEJ; Vicente et al., 2005), carry no further conventional hydrogen-bonding groups. Since both of these structures were reported on a proof-of-constitution basis, with no description or discussion of the intermolecular interactions, it is of interest briefly to compare the crystal structures of (II) and (III) with that of (I).

In each of (II) and (III), pairs of molecules related by inversion are linked, as in compound (I), into centrosymmetric R22(8) dimers by N—H···O hydrogen bonds which, as in (I), are fairly short and almost linear. In (II), a weak ππ stacking interaction involving the pendent phenyl rings in molecules related by inversion leads to a chain of π-stacked dimers running parallel to the [100] direction (Fig. 3), but otherwise rather similar to the chain in (I). There are no aromatic ππ stacking interactions in the structure of (III), despite the rich availability of aryl rings, but instead the hydrogen-bonded dimers are linked by two independent C—H···π(arene) hydrogen bonds to form sheets lying parallel to (100) (Fig. 4).

Experimental top

A mixture of 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine (100 mg, 1.0 mmol) and 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (1.0 mmol) in ethanol (4 ml) was heated under reflux with stirring for 2–3 h. After complete disappearance of the starting materials, as monitored by thin-layer chromatography, the mixture was cooled to ambient temperature. The resulting solid product was collected by filtration and then washed with cold ethanol (2 × 0.5 ml) to give the title compound, (I), as a yellow solid [yield 86%, m.p. 553 K (decomposition)]. MS (70 eV) m/z (%) = 370 (68) [M+], 313 (42), 287 (100), 262 (47), 226 (46), 128 (21), 77 (64). Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Refinement top

All H atoms were located in difference maps and then treated as riding atoms, with C—H = 0.95 (aromatic and heteroaromatic) or 0.98 Å (methyl) and N—H = 0.90 Å, and with Uiso(H) = kUeq(carrier), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000) and DENZO (Otwinowski & Minor, 1997); 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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom labelling 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. A stereoview of part of the crystal structure of (I), showing the formation of a chain parallel to [201] consisting of π-stacked hydrogen-bonded dimers. For the sake of clarity, H atoms bonded to C atoms have all been omitted.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (II), showing the formation of a chain parallel to [100] consisting of π-stacked hydrogen-bonded dimers. The original atom coordinates (Li et al., 2004) were used and, for the sake of clarity, H atoms bonded to C atoms have all been omitted.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (III), showing the formation of a sheet lying parallel to (100) and built from N—H···O and C—H···π(arene) hydrogen bonds. The original atom coordinates (Vicente et al., 2005) were used and, for the sake of clarity, H atoms not involved in the motifs shown have been omitted.
3-[(E)-(3-tert-Butyl-1-phenyl-1H-pyrazol-5- yl)iminomethyl]quinolin-2(1H)-one top
Crystal data top
C23H22N4OZ = 2
Mr = 370.45F(000) = 392
Triclinic, P1Dx = 1.310 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3601 (2) ÅCell parameters from 4310 reflections
b = 11.2750 (5) Åθ = 3.1–27.7°
c = 13.8028 (5) ŵ = 0.08 mm1
α = 105.972 (2)°T = 120 K
β = 91.253 (3)°Block, yellow
γ = 98.539 (2)°0.25 × 0.18 × 0.15 mm
V = 938.99 (6) Å3
Data collection top
Bruker Nonius APEXII CCD camera on κ goniostat
diffractometer
4310 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2929 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.064
Detector resolution: 4096 x 4096 pixels/ 62 x 62 mm pixels mm-1θmax = 27.7°, θmin = 3.1°
ϕ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
k = 1414
Tmin = 0.976, Tmax = 0.988l = 1718
19114 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.087P)2]
where P = (Fo2 + 2Fc2)/3
4310 reflections(Δ/σ)max = 0.001
256 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C23H22N4Oγ = 98.539 (2)°
Mr = 370.45V = 938.99 (6) Å3
Triclinic, P1Z = 2
a = 6.3601 (2) ÅMo Kα radiation
b = 11.2750 (5) ŵ = 0.08 mm1
c = 13.8028 (5) ÅT = 120 K
α = 105.972 (2)°0.25 × 0.18 × 0.15 mm
β = 91.253 (3)°
Data collection top
Bruker Nonius APEXII CCD camera on κ goniostat
diffractometer
4310 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
2929 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.988Rint = 0.064
19114 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å3
4310 reflectionsΔρmin = 0.37 e Å3
256 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.07790 (19)0.54618 (12)0.82098 (10)0.0193 (3)
N21.24783 (19)0.64070 (12)0.84355 (10)0.0196 (3)
C31.2008 (2)0.72280 (15)0.79653 (12)0.0196 (4)
C41.0022 (2)0.68206 (15)0.74239 (12)0.0211 (4)
H40.93470.72370.70240.025*
C50.9252 (2)0.56947 (15)0.75913 (12)0.0194 (4)
C111.0810 (2)0.44623 (15)0.86522 (12)0.0191 (4)
C120.8949 (2)0.37204 (16)0.87887 (13)0.0230 (4)
H120.76040.38540.85640.028*
C130.9070 (3)0.27905 (16)0.92519 (13)0.0256 (4)
H130.78010.22720.93280.031*
C141.1005 (3)0.26018 (16)0.96062 (13)0.0256 (4)
H141.10700.19710.99370.031*
C151.2852 (3)0.33464 (16)0.94712 (13)0.0262 (4)
H151.41900.32220.97110.031*
C161.2770 (2)0.42659 (15)0.89932 (13)0.0223 (4)
H161.40480.47630.88970.027*
C311.3484 (2)0.84403 (15)0.80774 (12)0.0215 (4)
C321.5553 (3)0.84860 (17)0.86792 (14)0.0293 (4)
H32A1.62680.77910.83300.044*
H32B1.52310.84160.93540.044*
H32C1.64880.92800.87390.044*
C331.3990 (3)0.85829 (16)0.70306 (13)0.0275 (4)
H33A1.26660.85830.66540.041*
H33B1.46790.78850.66630.041*
H33C1.49490.93720.71050.041*
C341.2366 (3)0.95237 (16)0.86376 (14)0.0285 (4)
H34A1.20460.94410.93100.043*
H34B1.10380.95020.82550.043*
H34C1.33011.03200.87060.043*
N510.74171 (19)0.48279 (12)0.72560 (10)0.0209 (3)
N610.05457 (19)0.37302 (12)0.55062 (10)0.0196 (3)
H610.04470.39980.51850.024*
C620.2434 (2)0.45435 (15)0.57510 (12)0.0187 (4)
O620.27221 (16)0.55038 (10)0.54628 (8)0.0228 (3)
C630.4025 (2)0.42005 (15)0.63598 (12)0.0192 (4)
C640.3608 (2)0.31132 (15)0.66188 (12)0.0203 (4)
H640.46770.28910.69950.024*
C64a0.1622 (2)0.22974 (15)0.63440 (12)0.0201 (4)
C650.1137 (3)0.12022 (16)0.66383 (13)0.0255 (4)
H650.21870.09550.70070.031*
C660.0840 (3)0.04811 (17)0.63997 (14)0.0297 (4)
H660.11530.02680.65940.036*
C670.2396 (3)0.08573 (17)0.58671 (14)0.0276 (4)
H670.37700.03620.57090.033*
C680.1967 (2)0.19274 (16)0.55698 (13)0.0241 (4)
H680.30370.21730.52100.029*
C68a0.0053 (2)0.26532 (15)0.57995 (12)0.0188 (4)
C690.5988 (2)0.50770 (15)0.67065 (12)0.0200 (4)
H690.62120.58380.65250.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0178 (7)0.0193 (7)0.0218 (8)0.0024 (5)0.0016 (5)0.0082 (6)
N20.0192 (7)0.0195 (7)0.0212 (7)0.0017 (5)0.0003 (5)0.0083 (6)
C30.0202 (8)0.0221 (9)0.0178 (8)0.0051 (6)0.0013 (6)0.0067 (7)
C40.0202 (8)0.0226 (9)0.0228 (9)0.0046 (6)0.0016 (6)0.0097 (7)
C50.0183 (8)0.0212 (9)0.0202 (9)0.0045 (6)0.0002 (6)0.0074 (7)
C110.0225 (8)0.0179 (8)0.0175 (8)0.0045 (6)0.0004 (6)0.0056 (7)
C120.0206 (8)0.0279 (9)0.0232 (9)0.0055 (7)0.0006 (7)0.0110 (7)
C130.0260 (9)0.0257 (9)0.0269 (10)0.0022 (7)0.0026 (7)0.0113 (8)
C140.0297 (9)0.0245 (9)0.0260 (10)0.0076 (7)0.0004 (7)0.0109 (8)
C150.0222 (8)0.0282 (10)0.0309 (10)0.0080 (7)0.0018 (7)0.0110 (8)
C160.0196 (8)0.0238 (9)0.0251 (9)0.0048 (7)0.0007 (7)0.0092 (7)
C310.0220 (8)0.0193 (9)0.0233 (9)0.0012 (6)0.0008 (7)0.0075 (7)
C320.0251 (9)0.0277 (10)0.0354 (11)0.0008 (7)0.0043 (7)0.0127 (8)
C330.0292 (9)0.0258 (9)0.0294 (10)0.0018 (7)0.0025 (7)0.0121 (8)
C340.0311 (9)0.0242 (9)0.0299 (10)0.0041 (7)0.0002 (7)0.0074 (8)
N510.0176 (7)0.0245 (8)0.0210 (8)0.0028 (5)0.0019 (5)0.0077 (6)
N610.0174 (7)0.0228 (8)0.0202 (7)0.0040 (5)0.0031 (5)0.0087 (6)
C620.0197 (8)0.0205 (9)0.0173 (8)0.0054 (6)0.0014 (6)0.0064 (7)
O620.0212 (6)0.0242 (7)0.0261 (7)0.0029 (5)0.0021 (5)0.0127 (5)
C630.0198 (8)0.0212 (9)0.0179 (8)0.0061 (6)0.0010 (6)0.0062 (7)
C640.0192 (8)0.0243 (9)0.0185 (9)0.0057 (6)0.0006 (6)0.0068 (7)
C64a0.0213 (8)0.0207 (9)0.0198 (9)0.0045 (6)0.0003 (6)0.0078 (7)
C650.0232 (9)0.0273 (10)0.0289 (10)0.0041 (7)0.0015 (7)0.0129 (8)
C660.0297 (10)0.0269 (10)0.0350 (11)0.0007 (7)0.0001 (8)0.0156 (8)
C670.0232 (9)0.0305 (10)0.0278 (10)0.0022 (7)0.0033 (7)0.0099 (8)
C680.0202 (8)0.0295 (10)0.0221 (9)0.0022 (7)0.0027 (7)0.0078 (7)
C68a0.0223 (8)0.0186 (9)0.0161 (8)0.0041 (6)0.0012 (6)0.0054 (7)
C690.0202 (8)0.0211 (9)0.0203 (9)0.0045 (6)0.0008 (6)0.0081 (7)
Geometric parameters (Å, º) top
N1—N21.3643 (18)C33—H33B0.9800
N1—C51.380 (2)C33—H33C0.9800
N1—C111.424 (2)C34—H34A0.9800
N2—C31.331 (2)C34—H34B0.9800
C3—C41.401 (2)C34—H34C0.9800
C3—C311.507 (2)N51—C691.282 (2)
C4—C51.374 (2)N61—C621.3719 (19)
C4—H40.9500N61—H610.900
C5—N511.3857 (19)C62—O621.2432 (19)
C11—C121.392 (2)C62—C631.462 (2)
C11—C161.392 (2)C63—C641.360 (2)
C12—C131.380 (2)C63—C691.453 (2)
C12—H120.9500C64—C64a1.424 (2)
C13—C141.381 (2)C64—H640.9500
C13—H130.9500C64a—C651.398 (2)
C14—C151.386 (2)C65—C661.372 (2)
C14—H140.9500C65—H650.9500
C15—C161.380 (2)C66—C671.402 (2)
C15—H150.9500C66—H660.9500
C16—H160.9500C67—C681.370 (2)
C31—C321.527 (2)C67—H670.9500
C31—C331.533 (2)C68—C68a1.396 (2)
C31—C341.536 (2)C68a—N611.378 (2)
C32—H32A0.9800C64a—C68a1.405 (2)
C32—H32B0.9800C68—H680.9500
C32—H32C0.9800C69—H690.9500
C33—H33A0.9800
N2—N1—C5110.84 (13)H33A—C33—H33B109.5
N2—N1—C11117.88 (12)C31—C33—H33C109.5
C5—N1—C11131.24 (13)H33A—C33—H33C109.5
C3—N2—N1105.59 (13)H33B—C33—H33C109.5
N2—C3—C4111.28 (14)C31—C34—H34A109.5
N2—C3—C31121.05 (14)C31—C34—H34B109.5
C4—C3—C31127.64 (15)H34A—C34—H34B109.5
C5—C4—C3105.79 (14)C31—C34—H34C109.5
C5—C4—H4127.1H34A—C34—H34C109.5
C3—C4—H4127.1H34B—C34—H34C109.5
C4—C5—N1106.50 (13)C69—N51—C5118.86 (14)
C4—C5—N51133.72 (15)C62—N61—C68a125.25 (13)
N1—C5—N51119.75 (14)C62—N61—H61113.9
C12—C11—C16119.64 (15)C68a—N61—H61120.5
C12—C11—N1122.09 (14)O62—C62—N61120.64 (14)
C16—C11—N1118.21 (14)O62—C62—C63123.65 (14)
C13—C12—C11119.63 (15)N61—C62—C63115.72 (14)
C13—C12—H12120.2C64—C63—C69122.03 (14)
C11—C12—H12120.2C64—C63—C62119.97 (14)
C12—C13—C14121.09 (15)C69—C63—C62117.94 (14)
C12—C13—H13119.5C63—C64—C64a122.17 (15)
C14—C13—H13119.5C63—C64—H64118.9
C13—C14—C15118.99 (16)C64a—C64—H64118.9
C13—C14—H14120.5C65—C64a—C68a119.05 (15)
C15—C14—H14120.5C65—C64a—C64122.89 (15)
C16—C15—C14120.84 (15)C68a—C64a—C64117.97 (15)
C16—C15—H15119.6C66—C65—C64a120.69 (16)
C14—C15—H15119.6C66—C65—H65119.7
C15—C16—C11119.78 (15)C64a—C65—H65119.7
C15—C16—H16120.1C65—C66—C67119.54 (17)
C11—C16—H16120.1C65—C66—H66120.2
C3—C31—C32110.99 (13)C67—C66—H66120.2
C3—C31—C33109.63 (13)C68—C67—C66121.07 (16)
C32—C31—C33109.54 (13)C68—C67—H67119.5
C3—C31—C34108.63 (13)C66—C67—H67119.5
C32—C31—C34108.98 (14)C67—C68—C68a119.47 (16)
C33—C31—C34109.03 (14)C67—C68—H68120.3
C31—C32—H32A109.5C68a—C68—H68120.3
C31—C32—H32B109.5N61—C68a—C68121.06 (14)
H32A—C32—H32B109.5N61—C68a—C64a118.77 (14)
C31—C32—H32C109.5C68—C68a—C64a120.17 (15)
H32A—C32—H32C109.5N51—C69—C63120.29 (15)
H32B—C32—H32C109.5N51—C69—H69119.9
C31—C33—H33A109.5C63—C69—H69119.9
C31—C33—H33B109.5
C5—N1—N2—C30.36 (17)C4—C3—C31—C3463.6 (2)
C11—N1—N2—C3177.51 (13)C4—C5—N51—C694.2 (3)
N1—N2—C3—C40.65 (17)N1—C5—N51—C69177.94 (14)
N1—N2—C3—C31177.23 (13)C68a—N61—C62—O62178.95 (14)
N2—C3—C4—C50.70 (18)C68a—N61—C62—C631.0 (2)
C31—C3—C4—C5177.00 (15)O62—C62—C63—C64178.03 (15)
C3—C4—C5—N10.44 (17)N61—C62—C63—C642.1 (2)
C3—C4—C5—N51178.54 (16)O62—C62—C63—C694.6 (2)
N2—N1—C5—C40.06 (18)N61—C62—C63—C69175.29 (13)
C11—N1—C5—C4177.57 (15)C69—C63—C64—C64a175.17 (14)
N2—N1—C5—N51178.48 (13)C62—C63—C64—C64a2.1 (2)
C11—N1—C5—N514.0 (3)C63—C64—C64a—C65177.37 (15)
N2—N1—C11—C12155.89 (14)C63—C64—C64a—C68a0.9 (2)
C5—N1—C11—C1221.5 (3)C68a—C64a—C65—C660.1 (3)
N2—N1—C11—C1621.4 (2)C64—C64a—C65—C66176.52 (16)
C5—N1—C11—C16161.24 (15)C64a—C65—C66—C670.9 (3)
C16—C11—C12—C130.6 (2)C65—C66—C67—C680.8 (3)
N1—C11—C12—C13177.87 (15)C66—C67—C68—C68a0.1 (3)
C11—C12—C13—C141.6 (3)C62—N61—C68a—C68175.63 (14)
C12—C13—C14—C151.4 (3)C62—N61—C68a—C64a3.9 (2)
C13—C14—C15—C160.2 (3)C67—C68—C68a—N61179.52 (15)
C14—C15—C16—C110.8 (3)C67—C68—C68a—C64a0.9 (2)
C12—C11—C16—C150.6 (2)C65—C64a—C68a—N61179.61 (14)
N1—C11—C16—C15176.77 (14)C64—C64a—C68a—N613.8 (2)
N2—C3—C31—C325.9 (2)C65—C64a—C68a—C680.8 (2)
C4—C3—C31—C32176.61 (15)C64—C64a—C68a—C68175.79 (14)
N2—C3—C31—C33127.02 (16)C5—N51—C69—C63178.71 (14)
C4—C3—C31—C3355.5 (2)C64—C63—C69—N511.6 (2)
N2—C3—C31—C34113.92 (16)N51—C69—C63—C62178.88 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N61—H61···O62i0.901.922.8110 (17)176
C12—H12···N510.952.372.951 (2)119
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC23H22N4O
Mr370.45
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)6.3601 (2), 11.2750 (5), 13.8028 (5)
α, β, γ (°)105.972 (2), 91.253 (3), 98.539 (2)
V3)938.99 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.18 × 0.15
Data collection
DiffractometerBruker Nonius APEXII CCD camera on κ goniostat
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.976, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
19114, 4310, 2929
Rint0.064
(sin θ/λ)max1)0.654
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.151, 1.04
No. of reflections4310
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.37

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000) and DENZO (Otwinowski & Minor, 1997), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
N61—C621.3719 (19)C66—C671.402 (2)
C62—C631.462 (2)C67—C681.370 (2)
C63—C641.360 (2)C68—C68a1.396 (2)
C64—C64a1.424 (2)C68a—N611.378 (2)
C64a—C651.398 (2)C64a—C68a1.405 (2)
C65—C661.372 (2)
N2—N1—C11—C12155.89 (14)N1—C5—N51—C69177.94 (14)
N2—C3—C31—C325.9 (2)C5—N51—C69—C63178.71 (14)
N2—C3—C31—C33127.02 (16)N51—C69—C63—C62178.88 (14)
N2—C3—C31—C34113.92 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N61—H61···O62i0.901.922.8110 (17)176
C12—H12···N510.952.372.951 (2)119
Symmetry code: (i) x, y+1, z+1.
 

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