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In the title compound, C29H30N6O, the naphthyridine moiety is planar with a dihedral angle between the fused rings of 1.9 (1)°. The phenol ring is nearly coplanar, while the diethyl­amino­phenyl substituent is orthogonal to the central naphthyridine ring and the pyrrolidine ring makes an angle of 11.2 (1)° with it. The O atom of the hydroxy substituent is coplanar with the phenyl ring to which it is attached. The molecular structure is stabilized by a C—H...N-type intramolecular hydrogen bond and the packing is stabilized by intermolecular C—H...π, O—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010100422X/na1495sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010100422X/na1495Isup2.hkl
Contains datablock I

CCDC reference: 166982

Comment top

Naphthyridine derivatives constitute an important class of compounds possessing diverse types of biological properties. They have been reported as potential drugs for the treatment of bladder function disorders (Natsugari et al., 1999). They also possess anti-tumor (el-Subbah et al., 1999), antibacterial (Domagala et al., 1993), tuberculostatic (Ferrarini et al., 1998), cardio-tonic (Mohan & Mishra, 1997), anticonvulsant and insecticidal (Damon & Nadelson, 1981) properties. 1,6-Naphthyridine derivatives have been tested pharmacologically as potent antagonists at adrenoreceptors (Brown et al., 1993), they are also used as novel potent adenosine 3',5'-cyclic phosphate phosphodiesterase III inhibitors (Singh et al., 1995). As a continuation of the studies on 1,6-napthyridine derivatives (Sankaranarayanan et al., 1999) and to have a better understanding of the influence of structural and conformational change on its biological activity, the X-ray crystal structure analysis of the title compound, (I), has been carried out. \sch

The five rings of the molecule are identified as: A (C5,N6,C7—C10), B (N1,C2—C4,C10,C9), C (C19—C24), D (N14,C15—C18), E (C25—C30). The N—C and the other bond distances are comparable with the related structures previously studied (Sankaranarayanan et al., 1999; Thirumurugan et al., 1999; Govindasamy et al., 2000). The bond distance C5—N11 is shorter than the typical C—N single bond distance (1.47 Å) indicating conjugation of amino group with the aromatic system of naphthyridine. The naphthyridine ring is planar with the dihedral angle between the fused pyridine rings (rings A and B) being 1.9 (1)°.

The least squares plane through the phenyl rings make a dihedral angle of 1.9 (1) (ring C) and 89.5 (1)° (ring E) with the ring B to which they are attached indicating the perpendicular orientation of the ring E. The best plane through the pyrrolidine ring makes a dihedral angle of 11.3 (1)° with the pyridine ring (A). The sum of the bond angles around N14 and N31 are 359.6 (3) and 358.2 (3)°, respectively, indicating sp2 hybridization. The cyano bond distance C12N13 agrees well with the literature value of 1.138 (7) Å (Allen et al., 1987). The orientation of the diethyl substituent with respect to the phenyl ring (E) can be described by the torsional angles C28—N31—C32—C33 = -122.5 (3), C28—N31—C34—C35 = 82.0 (3)°. O36 is co-planar [C20—C21—C22—O36 = 177.3 (2)°] with the phenyl ring (C) to which it is attached. Due to steric interactions, bond angles C4—C10—C5 [127.3 (2)°], C8—C7—N14 [125.1 (2)°] are widened and the bond angles N1—C9—C8 [116.7 (2)°], N1—C2—C19 = 116.3 (2) are narrowed from 120° and these observations are also found in related structures (Chinnakali et al., 1998).

Apart from the normal van der Waals interactions, the molecular structure is stabilized by an intramolecular C—H···N type hydrogen bond and the molecular packing by the intermolecular N—H···O and O—H···N hydrogen bonds and C—H···π interaction (Table 2), where Cg1 is a centroid of ring E.

Related literature top

For related literature, see: Allen et al. (1987); Brown et al. (1993); Chinnakali et al. (1998); Damon & Nadelson (1981); Domagala et al. (1993); Ferrarini et al. (1998); Govindasamy et al. (2000); Mohan & Mishra (1997); Nardelli (1999); Natsugari et al. (1999); Sankaranarayanan et al. (1999); Sheldrick (1997); Singh et al. (1995); Thirumurugan et al. (1999).

Experimental top

A solution of 4-methoxy-4'-hydroxybenzalacetophenone (2.4 mmol), malononitrile (4.8 mmol) and pyrrolidine (4.8 mmol) in ethanol (20 ml) was refluxed for 25 hrs. The solvent was removed under reduced pressure. The residue was purified by column chromatography. The solid thus obtained was recrystallized from ethanol-ethylacetate (1:1) solvent using slow evaporation technique.

Refinement top

The coordinates of hydroxyl H atom (H36) have been calculated with the computer program HYDROGEN (Nardelli, 1999). The calculated coordinates were 1.09571 0.80793 0.33758. By accepting these coordinates as such and keeping the distance between the O36 and H36 as 0.85 Å using the command DFIX in SHELXL (Sheldrick, 1997), the structure has been further refined. All other hydrogen atoms were included in calculated positions and allowed to ride on their corresponding parent atoms.

Structure description top

Naphthyridine derivatives constitute an important class of compounds possessing diverse types of biological properties. They have been reported as potential drugs for the treatment of bladder function disorders (Natsugari et al., 1999). They also possess anti-tumor (el-Subbah et al., 1999), antibacterial (Domagala et al., 1993), tuberculostatic (Ferrarini et al., 1998), cardio-tonic (Mohan & Mishra, 1997), anticonvulsant and insecticidal (Damon & Nadelson, 1981) properties. 1,6-Naphthyridine derivatives have been tested pharmacologically as potent antagonists at adrenoreceptors (Brown et al., 1993), they are also used as novel potent adenosine 3',5'-cyclic phosphate phosphodiesterase III inhibitors (Singh et al., 1995). As a continuation of the studies on 1,6-napthyridine derivatives (Sankaranarayanan et al., 1999) and to have a better understanding of the influence of structural and conformational change on its biological activity, the X-ray crystal structure analysis of the title compound, (I), has been carried out. \sch

The five rings of the molecule are identified as: A (C5,N6,C7—C10), B (N1,C2—C4,C10,C9), C (C19—C24), D (N14,C15—C18), E (C25—C30). The N—C and the other bond distances are comparable with the related structures previously studied (Sankaranarayanan et al., 1999; Thirumurugan et al., 1999; Govindasamy et al., 2000). The bond distance C5—N11 is shorter than the typical C—N single bond distance (1.47 Å) indicating conjugation of amino group with the aromatic system of naphthyridine. The naphthyridine ring is planar with the dihedral angle between the fused pyridine rings (rings A and B) being 1.9 (1)°.

The least squares plane through the phenyl rings make a dihedral angle of 1.9 (1) (ring C) and 89.5 (1)° (ring E) with the ring B to which they are attached indicating the perpendicular orientation of the ring E. The best plane through the pyrrolidine ring makes a dihedral angle of 11.3 (1)° with the pyridine ring (A). The sum of the bond angles around N14 and N31 are 359.6 (3) and 358.2 (3)°, respectively, indicating sp2 hybridization. The cyano bond distance C12N13 agrees well with the literature value of 1.138 (7) Å (Allen et al., 1987). The orientation of the diethyl substituent with respect to the phenyl ring (E) can be described by the torsional angles C28—N31—C32—C33 = -122.5 (3), C28—N31—C34—C35 = 82.0 (3)°. O36 is co-planar [C20—C21—C22—O36 = 177.3 (2)°] with the phenyl ring (C) to which it is attached. Due to steric interactions, bond angles C4—C10—C5 [127.3 (2)°], C8—C7—N14 [125.1 (2)°] are widened and the bond angles N1—C9—C8 [116.7 (2)°], N1—C2—C19 = 116.3 (2) are narrowed from 120° and these observations are also found in related structures (Chinnakali et al., 1998).

Apart from the normal van der Waals interactions, the molecular structure is stabilized by an intramolecular C—H···N type hydrogen bond and the molecular packing by the intermolecular N—H···O and O—H···N hydrogen bonds and C—H···π interaction (Table 2), where Cg1 is a centroid of ring E.

For related literature, see: Allen et al. (1987); Brown et al. (1993); Chinnakali et al. (1998); Damon & Nadelson (1981); Domagala et al. (1993); Ferrarini et al. (1998); Govindasamy et al. (2000); Mohan & Mishra (1997); Nardelli (1999); Natsugari et al. (1999); Sankaranarayanan et al. (1999); Sheldrick (1997); Singh et al. (1995); Thirumurugan et al. (1999).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. Molecular structure showing 50% probability displacement ellipsoids with the atom-numbering scheme.
5-Amino-4-(4-N,N-diethylaminophenyl)-2-(4'-hydroxyphenyl)-7- (pyrrolidin-1-yl)-1,6-naphthyridine-8-carbonitrile top
Crystal data top
C29H30N6OZ = 2
Mr = 478.59F(000) = 508
Triclinic, P1Dx = 1.255 Mg m3
a = 9.9502 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3680 (2) ÅCell parameters from 4453 reflections
c = 12.4995 (2) Åθ = 2.8–33.1°
α = 94.692 (1)°µ = 0.08 mm1
β = 94.319 (1)°T = 293 K
γ = 98.505 (1)°Block, yellow
V = 1266.03 (4) Å30.42 × 0.38 × 0.32 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
3707 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
ω scansh = 1110
6716 measured reflectionsk = 1212
4298 independent reflectionsl = 1414
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.090P)2 + 0.5843P]
where P = (Fo2 + 2Fc2)/3
4298 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.36 e Å3
1 restraintΔρmin = 0.36 e Å3
Crystal data top
C29H30N6Oγ = 98.505 (1)°
Mr = 478.59V = 1266.03 (4) Å3
Triclinic, P1Z = 2
a = 9.9502 (2) ÅMo Kα radiation
b = 10.3680 (2) ŵ = 0.08 mm1
c = 12.4995 (2) ÅT = 293 K
α = 94.692 (1)°0.42 × 0.38 × 0.32 mm
β = 94.319 (1)°
Data collection top
Siemens SMART CCD area detector
diffractometer
3707 reflections with I > 2σ(I)
6716 measured reflectionsRint = 0.020
4298 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.170H-atom parameters constrained
S = 1.01Δρmax = 0.36 e Å3
4298 reflectionsΔρmin = 0.36 e Å3
329 parameters
Special details top

Experimental. Data were collected over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set was over 99% complete. Crystal decay was monitored by repeating 30 initial frames at the end of data collection and analysing the duplicate reflections, it was found negligible.

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
N10.57700 (15)0.37368 (15)0.43346 (13)0.0417 (4)
C20.56388 (18)0.45321 (18)0.35720 (15)0.0409 (4)
C30.4413 (2)0.4458 (2)0.29186 (17)0.0486 (5)
H30.43450.50500.24040.058*
C40.33098 (19)0.35222 (18)0.30291 (16)0.0431 (4)
C50.24082 (19)0.16081 (19)0.40907 (17)0.0461 (5)
N60.25887 (16)0.08749 (16)0.48850 (15)0.0500 (4)
C70.3767 (2)0.10697 (19)0.55294 (16)0.0450 (4)
C80.48739 (18)0.20140 (19)0.53321 (15)0.0421 (4)
C90.46881 (18)0.28304 (18)0.44878 (15)0.0397 (4)
C100.34287 (18)0.26662 (18)0.38433 (16)0.0415 (4)
N110.11865 (18)0.13013 (19)0.35167 (18)0.0679 (6)
H11A0.06000.06700.36820.081*
H11B0.09920.17370.29840.081*
C120.6196 (2)0.2199 (2)0.58869 (16)0.0474 (5)
N130.72898 (19)0.2373 (2)0.62899 (17)0.0663 (6)
N140.37627 (17)0.02959 (17)0.63451 (15)0.0515 (4)
C150.2551 (2)0.0644 (2)0.6511 (2)0.0641 (6)
H15A0.23860.13590.59430.077*
H15B0.17480.02180.65320.077*
C160.2908 (4)0.1118 (4)0.7565 (3)0.1075 (12)
H16A0.22390.09330.80590.129*
H16B0.28860.20590.74740.129*
C170.4186 (4)0.0522 (5)0.7992 (3)0.1378 (19)
H17A0.47560.11830.81300.165*
H17B0.41150.00230.86710.165*
C180.4824 (2)0.0372 (3)0.7223 (2)0.0633 (6)
H18A0.50670.12610.75600.076*
H18B0.56330.00750.69690.076*
C190.68580 (19)0.55076 (18)0.34467 (15)0.0416 (4)
C200.8039 (2)0.5581 (2)0.41341 (16)0.0468 (5)
H200.80680.49910.46540.056*
C210.9171 (2)0.6510 (2)0.40619 (17)0.0489 (5)
H210.99480.65410.45320.059*
C220.91470 (19)0.73884 (18)0.32936 (18)0.0465 (5)
C230.7996 (2)0.7310 (2)0.25819 (19)0.0528 (5)
H230.79840.78820.20470.063*
C240.6870 (2)0.63865 (19)0.26630 (18)0.0489 (5)
H240.61010.63500.21830.059*
C250.20639 (19)0.34633 (18)0.22683 (16)0.0438 (4)
C260.1037 (2)0.4193 (2)0.24879 (17)0.0522 (5)
H260.11270.47410.31250.063*
C270.0112 (2)0.4125 (2)0.17857 (17)0.0521 (5)
H270.07850.46190.19650.063*
C280.0293 (2)0.3329 (2)0.08068 (16)0.0481 (5)
C290.0751 (2)0.2598 (2)0.05904 (19)0.0602 (6)
H290.06670.20450.00430.072*
C300.1896 (2)0.2682 (2)0.12968 (19)0.0582 (6)
H300.25790.22010.11180.070*
N310.1439 (2)0.3241 (2)0.00989 (16)0.0658 (5)
C320.2421 (3)0.4153 (3)0.0209 (3)0.0909 (10)
H32A0.21190.47660.08400.109*
H32B0.24200.46520.04140.109*
C330.3797 (4)0.3548 (5)0.0309 (5)0.1393 (18)
H33A0.43730.42100.03730.209*
H33B0.38180.30750.09380.209*
H33C0.41180.29530.03190.209*
C340.1551 (3)0.2462 (3)0.0928 (2)0.0727 (7)
H34A0.06700.25790.12200.087*
H34B0.21920.27860.14230.087*
C350.2010 (4)0.1021 (3)0.0870 (3)0.0954 (10)
H35A0.20610.05690.15770.143*
H35B0.28930.08920.05990.143*
H35C0.13690.06840.03980.143*
O361.02009 (16)0.83594 (15)0.32032 (15)0.0636 (5)
H361.091 (3)0.810 (3)0.349 (3)0.110 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0345 (8)0.0418 (8)0.0472 (9)0.0000 (6)0.0036 (6)0.0067 (7)
C20.0361 (9)0.0398 (9)0.0453 (10)0.0021 (8)0.0029 (8)0.0025 (8)
C30.0430 (11)0.0480 (11)0.0532 (11)0.0001 (8)0.0012 (9)0.0129 (9)
C40.0369 (9)0.0414 (10)0.0490 (11)0.0021 (8)0.0000 (8)0.0028 (8)
C50.0370 (10)0.0426 (10)0.0561 (12)0.0008 (8)0.0012 (8)0.0053 (9)
N60.0379 (9)0.0476 (9)0.0622 (11)0.0030 (7)0.0016 (8)0.0109 (8)
C70.0391 (10)0.0443 (10)0.0514 (11)0.0038 (8)0.0064 (8)0.0069 (8)
C80.0352 (9)0.0448 (10)0.0463 (10)0.0039 (8)0.0038 (8)0.0075 (8)
C90.0332 (9)0.0399 (9)0.0448 (10)0.0024 (7)0.0047 (7)0.0020 (8)
C100.0356 (9)0.0386 (9)0.0484 (10)0.0016 (8)0.0021 (8)0.0011 (8)
N110.0449 (10)0.0633 (12)0.0869 (14)0.0196 (9)0.0170 (9)0.0278 (10)
C120.0400 (11)0.0520 (11)0.0499 (11)0.0006 (8)0.0037 (9)0.0142 (9)
N130.0425 (10)0.0824 (14)0.0713 (13)0.0039 (9)0.0069 (9)0.0275 (11)
N140.0419 (9)0.0542 (10)0.0588 (10)0.0005 (7)0.0069 (8)0.0188 (8)
C150.0567 (13)0.0601 (13)0.0741 (15)0.0073 (11)0.0141 (11)0.0201 (12)
C160.101 (2)0.122 (3)0.093 (2)0.029 (2)0.0064 (18)0.060 (2)
C170.083 (2)0.204 (4)0.118 (3)0.044 (3)0.021 (2)0.114 (3)
C180.0532 (13)0.0720 (15)0.0662 (14)0.0025 (11)0.0047 (11)0.0301 (12)
C190.0365 (10)0.0406 (10)0.0463 (10)0.0013 (8)0.0042 (8)0.0032 (8)
C200.0417 (10)0.0488 (11)0.0485 (11)0.0003 (8)0.0026 (8)0.0109 (9)
C210.0369 (10)0.0523 (11)0.0548 (12)0.0012 (8)0.0003 (8)0.0061 (9)
C220.0371 (10)0.0382 (10)0.0636 (12)0.0006 (8)0.0098 (9)0.0055 (9)
C230.0478 (11)0.0470 (11)0.0647 (13)0.0033 (9)0.0055 (10)0.0197 (10)
C240.0393 (10)0.0477 (11)0.0589 (12)0.0030 (8)0.0017 (9)0.0118 (9)
C250.0384 (10)0.0421 (10)0.0487 (11)0.0000 (8)0.0016 (8)0.0073 (8)
C260.0531 (12)0.0528 (12)0.0482 (11)0.0089 (9)0.0041 (9)0.0042 (9)
C270.0461 (11)0.0542 (12)0.0556 (12)0.0138 (9)0.0047 (9)0.0003 (9)
C280.0424 (10)0.0516 (11)0.0476 (11)0.0007 (8)0.0035 (8)0.0081 (9)
C290.0545 (13)0.0696 (14)0.0515 (12)0.0071 (11)0.0038 (10)0.0120 (10)
C300.0461 (12)0.0625 (13)0.0636 (13)0.0117 (10)0.0019 (10)0.0068 (11)
N310.0580 (11)0.0751 (13)0.0603 (12)0.0157 (10)0.0199 (9)0.0050 (10)
C320.0761 (19)0.094 (2)0.098 (2)0.0290 (16)0.0347 (16)0.0123 (17)
C330.104 (3)0.127 (3)0.208 (5)0.045 (3)0.053 (3)0.055 (3)
C340.0722 (16)0.0873 (18)0.0524 (13)0.0064 (14)0.0156 (12)0.0008 (12)
C350.097 (2)0.086 (2)0.090 (2)0.0018 (17)0.0158 (17)0.0208 (17)
O360.0425 (8)0.0505 (9)0.0960 (13)0.0062 (7)0.0051 (8)0.0215 (8)
Geometric parameters (Å, º) top
N1—C21.322 (2)C20—C211.383 (3)
N1—C91.357 (2)C20—H200.9300
C2—C31.405 (3)C21—C221.378 (3)
C2—C191.487 (3)C21—H210.9300
C3—C41.377 (3)C22—O361.360 (2)
C3—H30.9300C22—C231.384 (3)
C4—C101.414 (3)C23—C241.378 (3)
C4—C251.495 (3)C23—H230.9300
C5—N61.316 (3)C24—H240.9300
C5—N111.346 (3)C25—C301.388 (3)
C5—C101.450 (3)C25—C261.389 (3)
N6—C71.351 (3)C26—C271.378 (3)
C7—N141.348 (3)C26—H260.9300
C7—C81.412 (3)C27—C281.403 (3)
C8—C121.419 (3)C27—H270.9300
C8—C91.424 (3)C28—N311.377 (3)
C9—C101.418 (3)C28—C291.403 (3)
N11—H11A0.8600C29—C301.376 (3)
N11—H11B0.8600C29—H290.9300
C12—N131.147 (3)C30—H300.9300
N14—C181.453 (3)N31—C341.447 (3)
N14—C151.473 (3)N31—C321.463 (3)
C15—C161.480 (4)C32—C331.438 (5)
C15—H15A0.9700C32—H32A0.9700
C15—H15B0.9700C32—H32B0.9700
C16—C171.377 (4)C33—H33A0.9600
C16—H16A0.9700C33—H33B0.9600
C16—H16B0.9700C33—H33C0.9600
C17—C181.500 (4)C34—C351.505 (4)
C17—H17A0.9700C34—H34A0.9700
C17—H17B0.9700C34—H34B0.9700
C18—H18A0.9700C35—H35A0.9600
C18—H18B0.9700C35—H35B0.9600
C19—C241.391 (3)C35—H35C0.9600
C19—C201.391 (3)O36—H360.85 (2)
C2—N1—C9118.9 (2)C21—C20—H20119.2
N1—C2—C3121.7 (2)C19—C20—H20119.2
N1—C2—C19116.3 (2)C22—C21—C20120.0 (2)
C3—C2—C19122.0 (2)C22—C21—H21120.0
C4—C3—C2121.0 (2)C20—C21—H21120.0
C4—C3—H3119.5O36—C22—C21123.2 (2)
C2—C3—H3119.5O36—C22—C23117.4 (2)
C3—C4—C10118.2 (2)C21—C22—C23119.4 (2)
C3—C4—C25117.8 (2)C24—C23—C22120.2 (2)
C10—C4—C25124.0 (2)C24—C23—H23119.9
N6—C5—N11114.5 (2)C22—C23—H23119.9
N6—C5—C10123.5 (2)C23—C24—C19121.4 (2)
N11—C5—C10122.0 (2)C23—C24—H24119.3
C5—N6—C7121.1 (2)C19—C24—H24119.3
N14—C7—N6114.0 (2)C30—C25—C26117.0 (2)
N14—C7—C8125.1 (2)C30—C25—C4120.9 (2)
N6—C7—C8121.0 (2)C26—C25—C4122.0 (2)
C7—C8—C12125.3 (2)C27—C26—C25121.6 (2)
C7—C8—C9118.5 (2)C27—C26—H26119.2
C12—C8—C9116.1 (2)C25—C26—H26119.2
N1—C9—C10123.0 (2)C26—C27—C28121.6 (2)
N1—C9—C8116.7 (2)C26—C27—H27119.2
C10—C9—C8120.4 (2)C28—C27—H27119.2
C4—C10—C9117.3 (2)N31—C28—C27122.4 (2)
C4—C10—C5127.3 (2)N31—C28—C29121.2 (2)
C9—C10—C5115.4 (2)C27—C28—C29116.4 (2)
C5—N11—H11A120.0C30—C29—C28121.3 (2)
C5—N11—H11B120.0C30—C29—H29119.3
H11A—N11—H11B120.0C28—C29—H29119.3
N13—C12—C8176.5 (2)C29—C30—C25122.0 (2)
C7—N14—C18126.3 (2)C29—C30—H30119.0
C7—N14—C15121.7 (2)C25—C30—H30119.0
C18—N14—C15111.6 (2)C28—N31—C34120.5 (2)
N14—C15—C16103.7 (2)C28—N31—C32122.0 (2)
N14—C15—H15A111.0C34—N31—C32115.7 (2)
C16—C15—H15A111.0C33—C32—N31114.8 (3)
N14—C15—H15B111.0C33—C32—H32A108.6
C16—C15—H15B111.0N31—C32—H32A108.6
H15A—C15—H15B109.0C33—C32—H32B108.6
C17—C16—C15110.8 (2)N31—C32—H32B108.6
C17—C16—H16A109.5H32A—C32—H32B107.5
C15—C16—H16A109.5C32—C33—H33A109.5
C17—C16—H16B109.5C32—C33—H33B109.5
C15—C16—H16B109.5H33A—C33—H33B109.5
H16A—C16—H16B108.1C32—C33—H33C109.5
C16—C17—C18110.1 (3)H33A—C33—H33C109.5
C16—C17—H17A109.6H33B—C33—H33C109.5
C18—C17—H17A109.6N31—C34—C35114.2 (2)
C16—C17—H17B109.6N31—C34—H34A108.7
C18—C17—H17B109.6C35—C34—H34A108.7
H17A—C17—H17B108.2N31—C34—H34B108.7
N14—C18—C17103.7 (2)C35—C34—H34B108.7
N14—C18—H18A111.0H34A—C34—H34B107.6
C17—C18—H18A111.0C34—C35—H35A109.5
N14—C18—H18B111.0C34—C35—H35B109.5
C17—C18—H18B111.0H35A—C35—H35B109.5
H18A—C18—H18B109.0C34—C35—H35C109.5
C24—C19—C20117.4 (2)H35A—C35—H35C109.5
C24—C19—C2122.3 (2)H35B—C35—H35C109.5
C20—C19—C2120.3 (2)C22—O36—H36106 (2)
C21—C20—C19121.5 (2)
C9—N1—C2—C30.2 (3)C15—C16—C17—C182.5 (6)
C9—N1—C2—C19179.7 (2)C7—N14—C18—C17169.6 (3)
N1—C2—C3—C42.0 (3)C15—N14—C18—C173.0 (3)
C19—C2—C3—C4178.1 (2)C16—C17—C18—N143.4 (5)
C2—C3—C4—C102.2 (3)N1—C2—C19—C24178.7 (2)
C2—C3—C4—C25177.0 (2)C3—C2—C19—C241.4 (3)
N11—C5—N6—C7180.0 (2)N1—C2—C19—C202.2 (3)
C10—C5—N6—C70.2 (3)C3—C2—C19—C20177.7 (2)
C5—N6—C7—N14176.1 (2)C24—C19—C20—C211.6 (3)
C5—N6—C7—C83.8 (3)C2—C19—C20—C21177.6 (2)
N14—C7—C8—C127.1 (3)C19—C20—C21—C220.2 (3)
N6—C7—C8—C12173.0 (2)C20—C21—C22—O36177.3 (2)
N14—C7—C8—C9175.1 (2)C20—C21—C22—C231.6 (3)
N6—C7—C8—C94.8 (3)O36—C22—C23—C24177.0 (2)
C2—N1—C9—C102.1 (3)C21—C22—C23—C242.0 (3)
C2—N1—C9—C8178.9 (2)C22—C23—C24—C190.6 (3)
C7—C8—C9—N1179.1 (2)C20—C19—C24—C231.2 (3)
C12—C8—C9—N12.9 (3)C2—C19—C24—C23178.0 (2)
C7—C8—C9—C101.8 (3)C3—C4—C25—C3090.1 (2)
C12—C8—C9—C10176.2 (2)C10—C4—C25—C3089.1 (3)
C3—C4—C10—C90.4 (3)C3—C4—C25—C2689.0 (2)
C25—C4—C10—C9178.8 (2)C10—C4—C25—C2691.9 (3)
C3—C4—C10—C5179.2 (2)C30—C25—C26—C271.4 (3)
C25—C4—C10—C50.1 (3)C4—C25—C26—C27179.5 (2)
N1—C9—C10—C41.8 (3)C25—C26—C27—C280.9 (3)
C8—C9—C10—C4179.2 (2)C26—C27—C28—N31179.5 (2)
N1—C9—C10—C5177.2 (2)C26—C27—C28—C290.7 (3)
C8—C9—C10—C51.8 (3)N31—C28—C29—C30179.9 (2)
N6—C5—C10—C4178.1 (2)C27—C28—C29—C301.1 (3)
N11—C5—C10—C41.7 (3)C28—C29—C30—C251.7 (4)
N6—C5—C10—C93.0 (3)C26—C25—C30—C291.8 (3)
N11—C5—C10—C9177.2 (2)C4—C25—C30—C29179.1 (2)
C7—C8—C12—N13153 (4)C27—C28—N31—C34176.7 (2)
C9—C8—C12—N1325 (4)C29—C28—N31—C344.5 (3)
N6—C7—N14—C18173.4 (2)C27—C28—N31—C3212.2 (4)
C8—C7—N14—C186.5 (3)C29—C28—N31—C32169.0 (3)
N6—C7—N14—C151.4 (3)C28—N31—C32—C33122.5 (3)
C8—C7—N14—C15178.5 (2)C34—N31—C32—C3372.3 (4)
C7—N14—C15—C16171.4 (3)C28—N31—C34—C3582.0 (3)
C18—N14—C15—C161.7 (3)C32—N31—C34—C35112.6 (3)
N14—C15—C16—C170.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···N10.932.442.775 (2)101
N11—H11A···O36i0.862.393.047 (2)134
O36—H36···N13ii0.851.942.759 (3)163
C32—H32B···Cg1iii0.972.873.716 (7)146
Symmetry codes: (i) x1, y1, z; (ii) x+2, y+1, z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC29H30N6O
Mr478.59
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.9502 (2), 10.3680 (2), 12.4995 (2)
α, β, γ (°)94.692 (1), 94.319 (1), 98.505 (1)
V3)1266.03 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.42 × 0.38 × 0.32
Data collection
DiffractometerSiemens SMART CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6716, 4298, 3707
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.170, 1.01
No. of reflections4298
No. of parameters329
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.36

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
N1—C21.322 (2)C7—N141.348 (3)
N1—C91.357 (2)C8—C121.419 (3)
C3—C41.377 (3)C12—N131.147 (3)
C5—N61.316 (3)N14—C181.453 (3)
C5—N111.346 (3)N14—C151.473 (3)
N6—C71.351 (3)
C2—N1—C9118.9 (2)C28—N31—C34120.5 (2)
C7—N14—C18126.3 (2)C28—N31—C32122.0 (2)
C7—N14—C15121.7 (2)C34—N31—C32115.7 (2)
C18—N14—C15111.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···N10.932.442.775 (2)101
N11—H11A···O36i0.862.393.047 (2)134
O36—H36···N13ii0.851.942.759 (3)163
C32—H32B···Cg1iii0.972.873.716 (7)146
Symmetry codes: (i) x1, y1, z; (ii) x+2, y+1, z+1; (iii) x, y+1, z.
 

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