PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o701.
Published online 2008 March 12. doi:  10.1107/S160053680800487X
PMCID: PMC2960986

6-Amino-1-benzyl-4-(4-chloro­phen­yl)-3-(4-pyrid­yl)-1,4-dihydro­pyrano[2,3-c]pyrazole-5-carbonitrile

Abstract

The crystal structure of the title compound, C25H18ClN5O, was determined in the course of our studies on the synthesis of 1,4-dihydro­pyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyrid­yl)-1H-pyrazol-5(4H)-one with p-chloro­aldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chloro­phenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chloro­phenyl and pyridine rings make a dihedral angle of 86.8 (2)°.

Related literature

The therapeutic potential of p38 mitogen-activated protein (MAP) kinase inhibitors for the treatment of inflammatory-associated diseases has been extensively reviewed (Kumar et al., 2003 [triangle]; Pargellis & Regan, 2003 [triangle]). The synthesis of the title compound was performed according to the published procedures (Dyachenko & Chernega, 2005 [triangle]; Dyachenko & Rusanov, 2004 [triangle]; Klokol et al., 1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o701-scheme1.jpg

Experimental

Crystal data

  • C25H18ClN5O
  • M r = 439.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o701-efi1.jpg
  • a = 5.7021 (11) Å
  • b = 17.795 (3) Å
  • c = 21.056 (9) Å
  • β = 90.954 (8)°
  • V = 2136.2 (11) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 1.81 mm−1
  • T = 193 (2) K
  • 0.46 × 0.12 × 0.08 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 [triangle]) T min = 0.825, T max = 0.998 (expected range = 0.725–0.865)
  • 4443 measured reflections
  • 4018 independent reflections
  • 2971 reflections with I > 2σ(I)
  • R int = 0.026
  • 3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.203
  • S = 1.07
  • 4018 reflections
  • 307 parameters
  • 66 restraints
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.64 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 [triangle]); program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800487X/nc2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800487X/nc2090Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The research was realised with EU financial support, part of the FP6 project ‘Macrocept’.

supplementary crystallographic information

Comment

p38 mitogen-activated protein (MAP) kinases are important enzymes in signal-transduction cascades which are responsive to stress stimuli, such as cytokines, ultraviolet irradiation, heat shock and osmotic shock, and are involved in cell transformation, proliferation, differentation and apoptosis. Until now there is a lack in new lead structures. Virtual screening of a database of compounds is one possibility to obtain new hints. The crystal structure of the title compound (Fig. 1) was used to consider a possible binding mode in the ATP pocket of the enzyme.

1,4-Dihydropyrano[2,3-c]pyrazole derivatives related to 2 have been published as crystal structures (Dyachenko & Rusanov, 2004). The nitrogen atoms N19 and N30 are involved in H-bond interactions with the amino group (N17) forming three-dimensional network (Fig. 2). The unsubstituted benzene ring is disordered in two orientations and was refined using a split model. The 1,4-Dihydropyrano[2,3-c]pyrazole moiety is almost planar and is nearly perpendiculare (83.7 (1)°) to the C20—C25 ring. The dihedral angle between the pyridine ring and the C20—C25 ring is 86.8 (2)°.

Experimental

1-Benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one (1): A solution of ethyl 3-oxo-3-(4-pyridyl)propanoate (7.76 mmol) and triethylamine (7.76 mmol) in ethanol (15 ml) was cooled with an ice-bath. 2-Benzylhydrazinium chloride (7.76 mmol) was added and the reaction mixture was heated up to 60 °C for three hours. The solvent was evaporated to yield 98% of 1.

6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (2): A mixture of p-chlorobenzaldehyde (0.80 mmol), malononitrile (0.80 mmol), N-methylmorpholine (0.80 mmol) in ethanol (10 ml) was stirred for one minute at room temperature. 1 was added and left to stand for one day. The precipitate formed was filtered and washed with ethanol and hexane. The compound was recrystallized from ethanol (31% yield).

Refinement

Hydrogen atoms attached to carbons were placed at calculated positions with C—H=0.95A% (aromatic) or 0.99–1.00 Å (sp3 C-atom). Hydrogen atom attached to N17 were located in diff. fourier maps. All H atoms were refined with fixed isotropic thermal parameters using a riding motion model with Uiso(H) = 1.2–1.5Ueq (parent atom). The phenyl ring C11 - C16 is disordered over two positions with s.o.f. of 0.55/0.45 and was refined as a rigid group.

Figures

Fig. 1.
PLATON (Spek, 2003) view of 2. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size.
Fig. 2.
Crystal packing of compound 2. View along a axis. Only important H atoms are shown. Hydrogen bonds and disorederd phenyl rings are shown with dashed lines.

Crystal data

C25H18ClN5OF000 = 912
Mr = 439.89Dx = 1.368 Mg m3
Monoclinic, P21/cCu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 5.7021 (11) Åθ = 30–42º
b = 17.795 (3) ŵ = 1.81 mm1
c = 21.056 (9) ÅT = 193 (2) K
β = 90.954 (8)ºNeedle, colourless
V = 2136.2 (11) Å30.46 × 0.12 × 0.08 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.026
Monochromator: graphiteθmax = 69.9º
T = 193(2) Kθmin = 3.3º
ω/2θ scansh = 0→6
Absorption correction: ψ scan(CORINC; Dräger & Gattow, 1971)k = 0→21
Tmin = 0.825, Tmax = 0.998l = −25→25
4443 measured reflections3 standard reflections
4018 independent reflections every 60 min
2971 reflections with I > 2σ(I) intensity decay: 2%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.203  w = 1/[σ2(Fo2) + (0.0991P)2 + 1.7529P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
4018 reflectionsΔρmax = 0.50 e Å3
307 parametersΔρmin = −0.64 e Å3
66 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/UeqOcc. (<1)
N10.9067 (5)0.26498 (14)0.08891 (12)0.0361 (6)
C20.7214 (5)0.31100 (16)0.08484 (13)0.0336 (6)
O30.6666 (4)0.34475 (12)0.02838 (9)0.0367 (5)
C40.4711 (5)0.38996 (16)0.03011 (13)0.0328 (6)
C50.3506 (5)0.40201 (16)0.08494 (13)0.0332 (6)
C60.4017 (5)0.36554 (17)0.14986 (13)0.0327 (6)
H60.26350.33410.16150.039*
C70.6089 (5)0.31463 (16)0.14147 (13)0.0330 (6)
C80.7427 (5)0.26449 (17)0.18021 (14)0.0340 (7)
N90.9221 (5)0.23499 (15)0.14809 (12)0.0372 (6)
C101.0661 (6)0.2425 (2)0.03898 (16)0.0438 (8)
H10A1.21880.22810.05850.053*0.55
H10B1.09330.28590.01060.053*0.55
H10C1.11200.28800.01520.053*0.45
H10D1.21000.22170.05930.053*0.45
C11A0.9722 (14)0.1768 (3)−0.0004 (3)0.060 (5)0.55
C12A0.9179 (14)0.1866 (3)−0.0645 (3)0.079 (2)0.55
H12A0.94150.2341−0.08400.095*0.55
C13A0.8290 (16)0.1269 (4)−0.1000 (3)0.106 (4)0.55
H13A0.79190.1336−0.14380.127*0.55
C14A0.7945 (17)0.0574 (4)−0.0714 (4)0.126 (5)0.55
H14A0.73380.0166−0.09570.151*0.55
C15A0.8488 (17)0.0477 (3)−0.0074 (4)0.134 (5)0.55
H15A0.82520.00020.01220.161*0.55
C16A0.9377 (16)0.1074 (4)0.0282 (2)0.100 (3)0.55
H16A0.97480.10070.07190.120*0.55
C11B0.9766 (14)0.1880 (5)−0.0057 (4)0.047 (4)0.45
C12B0.7484 (13)0.1612 (6)−0.0118 (4)0.091 (4)0.45
H12B0.63510.17430.01890.110*0.45
C13B0.6861 (16)0.1152 (6)−0.0627 (5)0.115 (5)0.45
H13B0.53020.0969−0.06680.138*0.45
C14B0.852 (2)0.0960 (7)−0.1075 (5)0.140 (7)0.45
H14B0.80940.0646−0.14230.169*0.45
C15B1.080 (2)0.1229 (8)−0.1014 (6)0.249 (14)0.45
H15B1.19360.1098−0.13210.299*0.45
C16B1.1425 (14)0.1689 (7)−0.0505 (6)0.122 (5)0.45
H16B1.29850.1872−0.04640.146*0.45
N170.4223 (3)0.41620 (8)−0.02841 (6)0.0399 (6)
H17A0.51160.3977−0.06030.060*
H17B0.28700.4458−0.03550.060*
C180.1547 (3)0.45076 (8)0.08023 (6)0.0361 (7)
N19−0.0041 (3)0.49044 (8)0.07707 (6)0.0465 (7)
C200.4394 (3)0.42549 (8)0.20151 (6)0.0333 (6)
C210.2730 (3)0.43846 (8)0.24634 (6)0.0660 (12)
H210.13340.40930.24620.079*
C220.3071 (9)0.4943 (3)0.2924 (2)0.0825 (16)
H220.18970.50390.32290.099*
C230.5087 (8)0.5345 (2)0.29324 (17)0.0548 (10)
C240.6723 (8)0.5225 (2)0.2495 (2)0.0604 (10)
H240.81280.55120.25040.072*
C250.6371 (7)0.4684 (2)0.20311 (18)0.0543 (9)
H250.75300.46100.17180.065*
Cl260.5572 (3)0.60204 (7)0.35216 (6)0.0929 (5)
C270.7013 (6)0.23447 (17)0.24463 (14)0.0368 (7)
C280.8630 (7)0.1865 (2)0.27282 (18)0.0548 (9)
H281.00780.17670.25270.066*
C290.8138 (7)0.1527 (2)0.33022 (18)0.0588 (10)
H290.92750.11960.34820.071*
N300.6181 (6)0.16380 (18)0.36153 (13)0.0514 (8)
C310.4668 (7)0.2105 (3)0.33473 (18)0.0625 (11)
H310.32610.22050.35670.075*
C320.4972 (7)0.2462 (2)0.27684 (18)0.0581 (10)
H320.37860.27810.25980.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0401 (14)0.0352 (13)0.0331 (13)−0.0005 (11)0.0039 (10)−0.0038 (10)
C20.0419 (17)0.0304 (14)0.0286 (14)−0.0032 (12)0.0020 (12)−0.0020 (11)
O30.0438 (12)0.0397 (11)0.0268 (10)0.0027 (9)0.0048 (8)−0.0002 (8)
C40.0413 (16)0.0289 (14)0.0282 (14)−0.0028 (12)0.0011 (12)−0.0017 (11)
C50.0387 (16)0.0333 (15)0.0277 (14)−0.0012 (12)0.0030 (12)−0.0006 (11)
C60.0382 (16)0.0336 (15)0.0265 (14)−0.0035 (12)0.0037 (11)0.0002 (11)
C70.0377 (16)0.0317 (14)0.0297 (14)−0.0038 (12)0.0032 (12)−0.0022 (11)
C80.0381 (16)0.0321 (15)0.0319 (15)−0.0040 (12)0.0010 (12)−0.0003 (12)
N90.0420 (14)0.0356 (13)0.0341 (13)−0.0002 (11)0.0008 (11)−0.0014 (10)
C100.0424 (18)0.0462 (19)0.0433 (18)−0.0002 (15)0.0096 (14)−0.0066 (15)
C11A0.096 (11)0.045 (5)0.040 (6)−0.010 (5)0.008 (5)−0.024 (4)
C12A0.119 (6)0.067 (5)0.052 (4)0.008 (5)−0.023 (4)0.002 (4)
C13A0.142 (8)0.101 (7)0.074 (6)0.009 (6)−0.036 (6)−0.025 (6)
C14A0.167 (9)0.110 (8)0.100 (7)−0.041 (7)−0.009 (7)−0.030 (6)
C15A0.187 (9)0.098 (7)0.116 (8)−0.044 (7)−0.008 (7)−0.020 (6)
C16A0.149 (8)0.074 (5)0.077 (5)−0.039 (6)−0.010 (5)−0.005 (4)
C11B0.042 (7)0.048 (5)0.050 (7)0.003 (5)0.003 (5)0.003 (5)
C12B0.077 (6)0.090 (7)0.107 (7)−0.008 (5)−0.003 (6)−0.054 (6)
C13B0.104 (8)0.113 (8)0.129 (9)0.000 (7)−0.007 (7)−0.036 (7)
C14B0.155 (11)0.131 (10)0.135 (11)−0.040 (8)0.000 (8)−0.049 (8)
C15B0.248 (16)0.252 (16)0.248 (16)−0.014 (10)0.019 (10)−0.033 (10)
C16B0.129 (9)0.128 (9)0.110 (8)−0.033 (7)0.036 (7)−0.057 (7)
N170.0501 (16)0.0441 (15)0.0255 (12)0.0034 (12)0.0042 (11)0.0018 (11)
C180.0428 (17)0.0410 (17)0.0248 (14)−0.0051 (14)0.0044 (12)−0.0004 (12)
N190.0488 (17)0.0581 (18)0.0329 (14)0.0104 (15)0.0056 (12)0.0024 (12)
C200.0396 (16)0.0359 (15)0.0244 (13)0.0051 (13)0.0006 (11)−0.0005 (11)
C210.052 (2)0.091 (3)0.056 (2)−0.008 (2)0.0152 (18)−0.032 (2)
C220.075 (3)0.112 (4)0.061 (3)0.011 (3)0.018 (2)−0.046 (3)
C230.072 (3)0.047 (2)0.0450 (19)0.0216 (19)−0.0219 (18)−0.0117 (16)
C240.069 (3)0.048 (2)0.064 (2)−0.0149 (19)−0.002 (2)−0.0152 (18)
C250.059 (2)0.051 (2)0.053 (2)−0.0166 (18)0.0170 (17)−0.0129 (17)
Cl260.1409 (12)0.0647 (7)0.0714 (7)0.0405 (7)−0.0474 (8)−0.0352 (6)
C270.0437 (17)0.0337 (15)0.0330 (15)−0.0048 (13)−0.0019 (13)0.0017 (12)
C280.054 (2)0.062 (2)0.049 (2)0.0111 (18)0.0050 (17)0.0155 (17)
C290.065 (2)0.062 (2)0.049 (2)0.008 (2)0.0004 (18)0.0187 (18)
N300.0636 (19)0.0524 (18)0.0380 (15)−0.0055 (15)−0.0010 (14)0.0104 (13)
C310.061 (2)0.081 (3)0.046 (2)0.008 (2)0.0127 (18)0.020 (2)
C320.058 (2)0.070 (3)0.047 (2)0.015 (2)0.0106 (17)0.0203 (18)

Geometric parameters (Å, °)

N1—C21.338 (4)C11B—C16B1.3900
N1—N91.357 (3)C12B—C13B1.3900
N1—C101.457 (4)C12B—H12B0.9500
C2—O31.364 (3)C13B—C14B1.3900
C2—C71.365 (4)C13B—H13B0.9500
O3—C41.376 (4)C14B—C15B1.3900
C4—N171.342 (3)C14B—H14B0.9500
C4—C51.370 (4)C15B—C16B1.3900
C5—C181.416 (3)C15B—H15B0.9500
C5—C61.537 (4)C16B—H16B0.9500
C6—C71.502 (4)N17—H17A0.9113
C6—C201.536 (3)N17—H17B0.9442
C6—H61.0000C18—N191.1496
C7—C81.422 (4)C20—C251.362 (4)
C8—N91.342 (4)C20—C211.3687
C8—C271.481 (4)C21—C221.401 (5)
C10—C11B1.438 (7)C21—H210.9500
C10—C11A1.524 (5)C22—C231.354 (7)
C10—H10A0.9900C22—H220.9500
C10—H10B0.9900C23—C241.338 (6)
C10—H10C0.9900C23—Cl261.746 (4)
C10—H10D0.9900C24—C251.385 (5)
C11A—C12A1.3900C24—H240.9500
C11A—C16A1.3900C25—H250.9500
C12A—C13A1.3900C27—C321.373 (5)
C12A—H12A0.9500C27—C281.383 (5)
C13A—C14A1.3900C28—C291.382 (5)
C13A—H13A0.9500C28—H280.9500
C14A—C15A1.3900C29—N301.320 (5)
C14A—H14A0.9500C29—H290.9500
C15A—C16A1.3900N30—C311.318 (5)
C15A—H15A0.9500C31—C321.387 (5)
C16A—H16A0.9500C31—H310.9500
C11B—C12B1.3900C32—H320.9500
C2—N1—N9109.8 (2)C14A—C15A—H15A120.0
C2—N1—C10128.6 (3)C15A—C16A—C11A120.0
N9—N1—C10121.5 (3)C15A—C16A—H16A120.0
N1—C2—O3119.7 (2)C11A—C16A—H16A120.0
N1—C2—C7110.8 (3)C12B—C11B—C16B120.0
O3—C2—C7129.5 (3)C12B—C11B—C10127.8 (6)
C2—O3—C4114.1 (2)C16B—C11B—C10111.8 (6)
N17—C4—C5128.3 (3)C13B—C12B—C11B120.0
N17—C4—O3109.6 (2)C13B—C12B—H12B120.0
C5—C4—O3122.1 (3)C11B—C12B—H12B120.0
C4—C5—C18116.3 (2)C12B—C13B—C14B120.0
C4—C5—C6126.4 (3)C12B—C13B—H13B120.0
C18—C5—C6117.3 (2)C14B—C13B—H13B120.0
C7—C6—C20113.6 (2)C15B—C14B—C13B120.0
C7—C6—C5106.7 (2)C15B—C14B—H14B120.0
C20—C6—C5111.0 (2)C13B—C14B—H14B120.0
C7—C6—H6108.4C14B—C15B—C16B120.0
C20—C6—H6108.4C14B—C15B—H15B120.0
C5—C6—H6108.4C16B—C15B—H15B120.0
C2—C7—C8102.5 (3)C15B—C16B—C11B120.0
C2—C7—C6120.9 (3)C15B—C16B—H16B120.0
C8—C7—C6136.6 (3)C11B—C16B—H16B120.0
N9—C8—C7111.2 (3)C4—N17—H17A116.2
N9—C8—C27117.1 (3)C4—N17—H17B119.7
C7—C8—C27131.3 (3)H17A—N17—H17B123.3
C8—N9—N1105.7 (2)N19—C18—C5179.30 (13)
C11B—C10—N1116.0 (4)C25—C20—C21118.13 (16)
C11B—C10—C11A8.3 (5)C25—C20—C6120.9 (2)
N1—C10—C11A112.7 (4)C21—C20—C6120.99 (12)
C11B—C10—H10A113.4C20—C21—C22120.5 (2)
N1—C10—H10A109.1C20—C21—H21119.7
C11A—C10—H10A109.1C22—C21—H21119.7
C11B—C10—H10B100.8C23—C22—C21119.4 (3)
N1—C10—H10B109.1C23—C22—H22120.3
C11A—C10—H10B109.1C21—C22—H22120.3
H10A—C10—H10B107.8C24—C23—C22120.6 (3)
C11B—C10—H10C108.3C24—C23—Cl26119.6 (3)
N1—C10—H10C108.3C22—C23—Cl26119.8 (3)
C11A—C10—H10C116.4C23—C24—C25120.1 (4)
H10A—C10—H10C100.5C23—C24—H24119.9
H10B—C10—H10C8.5C25—C24—H24119.9
C11B—C10—H10D108.3C20—C25—C24121.2 (3)
N1—C10—H10D108.3C20—C25—H25119.4
C11A—C10—H10D103.3C24—C25—H25119.4
H10A—C10—H10D7.3C32—C27—C28116.5 (3)
H10B—C10—H10D114.5C32—C27—C8123.2 (3)
H10C—C10—H10D107.4C28—C27—C8120.0 (3)
C12A—C11A—C16A120.0C29—C28—C27120.0 (4)
C12A—C11A—C10120.2 (4)C29—C28—H28120.0
C16A—C11A—C10119.8 (4)C27—C28—H28120.0
C11A—C12A—C13A120.0N30—C29—C28123.8 (4)
C11A—C12A—H12A120.0N30—C29—H29118.1
C13A—C12A—H12A120.0C28—C29—H29118.1
C12A—C13A—C14A120.0C31—N30—C29115.7 (3)
C12A—C13A—H13A120.0N30—C31—C32125.0 (4)
C14A—C13A—H13A120.0N30—C31—H31117.5
C13A—C14A—C15A120.0C32—C31—H31117.5
C13A—C14A—H14A120.0C27—C32—C31118.9 (4)
C15A—C14A—H14A120.0C27—C32—H32120.5
C16A—C15A—C14A120.0C31—C32—H32120.5
C16A—C15A—H15A120.0
N9—N1—C2—O3−177.1 (2)C13A—C14A—C15A—C16A0.0
C10—N1—C2—O3−1.6 (5)C14A—C15A—C16A—C11A0.0
N9—N1—C2—C71.2 (3)C12A—C11A—C16A—C15A0.0
C10—N1—C2—C7176.6 (3)C10—C11A—C16A—C15A179.0 (7)
N1—C2—O3—C4179.3 (3)N1—C10—C11B—C12B8.6 (10)
C7—C2—O3—C41.4 (4)C11A—C10—C11B—C12B76 (4)
C2—O3—C4—N17−175.7 (2)N1—C10—C11B—C16B−178.7 (6)
C2—O3—C4—C52.8 (4)C11A—C10—C11B—C16B−111 (4)
N17—C4—C5—C18−2.8 (4)C16B—C11B—C12B—C13B0.0
O3—C4—C5—C18179.0 (2)C10—C11B—C12B—C13B172.3 (10)
N17—C4—C5—C6174.6 (3)C11B—C12B—C13B—C14B0.0
O3—C4—C5—C6−3.5 (5)C12B—C13B—C14B—C15B0.0
C4—C5—C6—C70.2 (4)C13B—C14B—C15B—C16B0.0
C18—C5—C6—C7177.6 (2)C14B—C15B—C16B—C11B0.0
C4—C5—C6—C20124.6 (3)C12B—C11B—C16B—C15B0.0
C18—C5—C6—C20−58.0 (3)C10—C11B—C16B—C15B−173.4 (9)
N1—C2—C7—C8−1.2 (3)C4—C5—C18—N19−160 (100)
O3—C2—C7—C8176.8 (3)C6—C5—C18—N1922 (11)
N1—C2—C7—C6177.1 (3)C7—C6—C20—C2548.8 (3)
O3—C2—C7—C6−4.8 (5)C5—C6—C20—C25−71.5 (3)
C20—C6—C7—C2−119.2 (3)C7—C6—C20—C21−132.64 (18)
C5—C6—C7—C23.6 (4)C5—C6—C20—C21107.0 (2)
C20—C6—C7—C858.5 (4)C25—C20—C21—C22−0.1 (3)
C5—C6—C7—C8−178.8 (3)C6—C20—C21—C22−178.7 (3)
C2—C7—C8—N90.9 (3)C20—C21—C22—C23−1.4 (6)
C6—C7—C8—N9−177.0 (3)C21—C22—C23—C241.7 (7)
C2—C7—C8—C27−171.3 (3)C21—C22—C23—Cl26−177.8 (3)
C6—C7—C8—C2710.8 (6)C22—C23—C24—C25−0.4 (7)
C7—C8—N9—N1−0.2 (3)Cl26—C23—C24—C25179.1 (3)
C27—C8—N9—N1173.2 (2)C21—C20—C25—C241.4 (5)
C2—N1—N9—C8−0.6 (3)C6—C20—C25—C24180.0 (3)
C10—N1—N9—C8−176.4 (3)C23—C24—C25—C20−1.2 (6)
C2—N1—C10—C11B−75.7 (6)N9—C8—C27—C32−164.6 (3)
N9—N1—C10—C11B99.3 (6)C7—C8—C27—C327.2 (5)
C2—N1—C10—C11A−84.0 (5)N9—C8—C27—C289.2 (5)
N9—N1—C10—C11A91.0 (4)C7—C8—C27—C28−179.0 (3)
C11B—C10—C11A—C12A0(3)C32—C27—C28—C290.5 (6)
N1—C10—C11A—C12A115.3 (5)C8—C27—C28—C29−173.7 (3)
C11B—C10—C11A—C16A−179 (4)C27—C28—C29—N30−0.7 (7)
N1—C10—C11A—C16A−63.8 (6)C28—C29—N30—C31−0.3 (6)
C16A—C11A—C12A—C13A0.0C29—N30—C31—C321.6 (7)
C10—C11A—C12A—C13A−179.0 (7)C28—C27—C32—C310.6 (6)
C11A—C12A—C13A—C14A0.0C8—C27—C32—C31174.6 (4)
C12A—C13A—C14A—C15A0.0N30—C31—C32—C27−1.7 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N17—H17A···N30i0.912.082.955 (3)162
N17—H17B···N19ii0.942.153.068 (3)165

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2090).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435–436.
  • Dräger, M. & Gattow, G. (1971). Acta Chem. Scand.25, 761–762.
  • Dyachenko, V. D. & Chernega, A. N. (2005). Russ. J. Gen. Chem.75, 952–960.
  • Dyachenko, V. D. & Rusanov, E. B. (2004). Chem. Heterocycl. Compd.40, 231–240.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Klokol, G. V., Krivokolysko, S. G., Dyachenko, V. D. & Litvinov, V. P. (1999). Chem. Heterocycl. Compd, 35, 1183–1186.
  • Kumar, S., Boehm, J. & Lee, J. C. (2003). Nat. Rev. Drug Discov. 2, 717–726. [PubMed]
  • Pargellis, C. & Regan, J. (2003). Curr. Opin. Investig. Drugs, 4, 566–571. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography