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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

6-Benzyl-3-[(6-chloro­pyridin-3-yl)meth­yl]-6,7-di­hydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

aDepartment of Oncology, Renmin Hospital, Hubei University of Medicine, Shiyan 442000, Hubei, People's Republic of China, and bInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, Hubei, People's Republic of China
*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 6 November 2011; accepted 9 November 2011; online 16 November 2011)

The title compound, C17H14ClN7, crystallizes with two independent mol­ecules in the asymmetric unit. Inter­molecular N—H⋯N and C—H⋯N hydrogen bonds contribute to the stability of the crystal structure. In addition, weak C—H⋯π and ππ stacking [centroid–centroid distances of 3.699 (8) and 3.699 (6) Å] interactions are observed.

Related literature

For the biological activity of 1,2,3-triazoles, see: Santana et al. (2002[Santana, L., Teijeira, M., Uriarte, E., Balzarini, J. & De Clercq, E. (2002). Eur. J. Med. Chem. 37, 755-760.]); Zhao et al. (2005[Zhao, J. F., Xie, C., Ding, M. W. & He, H. W. (2005). Synthesis, 15, 2544-2549.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14ClN7

  • Mr = 351.80

  • Triclinic, [P \overline 1]

  • a = 6.1090 (7) Å

  • b = 8.9537 (11) Å

  • c = 31.292 (4) Å

  • α = 83.141 (1)°

  • β = 88.896 (1)°

  • γ = 75.184 (1)°

  • V = 1642.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 296 K

  • 0.47 × 0.39 × 0.21 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.892, Tmax = 0.950

  • 12520 measured reflections

  • 6071 independent reflections

  • 4578 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.123

  • S = 1.03

  • 6071 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the N2–N4/C8/C7 and C12–C17 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N14—H14A⋯N5i 0.86 2.60 3.457 (3) 173
N7—H7A⋯N12ii 0.86 2.53 3.389 (3) 174
C5—H5⋯N14iii 0.93 2.58 3.506 (3) 177
C10—H10⋯N11iii 0.93 2.42 3.240 (3) 147
C27—H27⋯N4iv 0.93 2.36 3.191 (3) 149
C23—H23ACg4v 0.97 2.58 3.509 (3) 160
C28—H28BCg1 0.97 2.93 3.506 (3) 120
Symmetry codes: (i) x+1, y-1, z; (ii) x+1, y, z; (iii) x-1, y+1, z; (iv) x-1, y, z; (v) x, y-1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2000[Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Neonicotinoids are a promising class of insecticides with excellent chemical and biological properties. 1,2,3-Triazoles have also received much attention because of their wide range of applications and biological activities such as anti-HIV and antimicrobial agents (Santana et al., 2002; Zhao et al., 2005). We report here the crystal structure of (I) (Fig. 1, Table 1), which was synthesized by introducing a pyridine ring into a 1,2,3-triazolo[4,5-d]pyrimidine molecular framework.

Significant intremolecular N—H···N and intramolecular C—H···N contribute strongly to the stability of the molecular configuration (Table 1). The crystal structure (Fig. 2) is stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1) and by ππ stacking interactions with centroid-centroid separations of 3.699 (8) and 3.699 (6) Å for Cg3···Cg6i and Cg6···Cg3ii, respectively, where Cg3 and Cg6 are the centroids of rings N5/C7—C9/N6/C10 and N9—N11/C25—C24, respectively [symmetry code: (i) X, 1+Y, Z, (ii) 3X, -1+Y, Z,].

Related literature top

For the biological activity of 1,2,3-triazoles, see: Santana et al. (2002); Zhao et al. (2005).

Experimental top

To a solution of ethyl N-3-((6-chloropyridin-3-yl)methyl)-5-cyano-3H- 1,2,3-triazol-4-ylformimidate (2 mmol) in anhydrous acetonitrile (15 ml) was added dropwise benzylamine (2 mmol) in anhydrous acetonitrile (6 ml) at room temperature. The mixture was stirred at room temperature until the reaction finished (monitored by thin layer chromatography),the solid was filtered and recrystallized from anhydrous acetonitrile to give the title compound(yield 83%). A colourless crystal grown from anhydrous acetonitrile was selected for X-ray structure analysis.

Refinement top

H atoms were placed in calculated positions, with C—H distances in the range 0.93–0.97 Å and N—H distances of 0.86 Å, and included in the final cycles of refinement using a riding-model approximation, with Uiso(H) = 1.2–1.5Ueq(carrier atom). A rotating group model was used for the methyl groups.

Structure description top

Neonicotinoids are a promising class of insecticides with excellent chemical and biological properties. 1,2,3-Triazoles have also received much attention because of their wide range of applications and biological activities such as anti-HIV and antimicrobial agents (Santana et al., 2002; Zhao et al., 2005). We report here the crystal structure of (I) (Fig. 1, Table 1), which was synthesized by introducing a pyridine ring into a 1,2,3-triazolo[4,5-d]pyrimidine molecular framework.

Significant intremolecular N—H···N and intramolecular C—H···N contribute strongly to the stability of the molecular configuration (Table 1). The crystal structure (Fig. 2) is stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1) and by ππ stacking interactions with centroid-centroid separations of 3.699 (8) and 3.699 (6) Å for Cg3···Cg6i and Cg6···Cg3ii, respectively, where Cg3 and Cg6 are the centroids of rings N5/C7—C9/N6/C10 and N9—N11/C25—C24, respectively [symmetry code: (i) X, 1+Y, Z, (ii) 3X, -1+Y, Z,].

For the biological activity of 1,2,3-triazoles, see: Santana et al. (2002); Zhao et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I), showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial view of the crystal packing of (I), showing the formation of N—H···N hydrogen-bonds as dashed lines.
6-Benzyl-3-[(6-chloropyridin-3-yl)methyl]-6,7-dihydro-3H- 1,2,3-triazolo[4,5-d]pyrimidin-7-imine top
Crystal data top
C17H14ClN7Z = 4
Mr = 351.80F(000) = 728
Triclinic, P1Dx = 1.422 Mg m3
a = 6.1090 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9537 (11) ÅCell parameters from 4552 reflections
c = 31.292 (4) Åθ = 2.4–25.5°
α = 83.141 (1)°µ = 0.25 mm1
β = 88.896 (1)°T = 296 K
γ = 75.184 (1)°Block, colourless
V = 1642.8 (3) Å30.47 × 0.39 × 0.21 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6071 independent reflections
Radiation source: fine-focus sealed tube4578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 77
Tmin = 0.892, Tmax = 0.950k = 1010
12520 measured reflectionsl = 3737
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0474P)2 + 0.785P]
where P = (Fo2 + 2Fc2)/3
6071 reflections(Δ/σ)max < 0.001
451 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C17H14ClN7γ = 75.184 (1)°
Mr = 351.80V = 1642.8 (3) Å3
Triclinic, P1Z = 4
a = 6.1090 (7) ÅMo Kα radiation
b = 8.9537 (11) ŵ = 0.25 mm1
c = 31.292 (4) ÅT = 296 K
α = 83.141 (1)°0.47 × 0.39 × 0.21 mm
β = 88.896 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6071 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
4578 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.950Rint = 0.018
12520 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.03Δρmax = 0.46 e Å3
6071 reflectionsΔρmin = 0.52 e Å3
451 parameters
Special details top

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
C10.7744 (4)0.6857 (3)0.05951 (7)0.0532 (6)
C21.0038 (4)0.6342 (4)0.05984 (9)0.0751 (8)
H21.07890.57610.03870.090*
C31.1206 (4)0.6708 (3)0.09232 (8)0.0662 (7)
H31.27770.63650.09370.079*
C41.0060 (3)0.7576 (2)0.12262 (6)0.0405 (5)
C50.7759 (4)0.8021 (3)0.11902 (8)0.0650 (7)
H50.69590.85970.13980.078*
C61.1269 (4)0.8060 (2)0.15811 (7)0.0469 (5)
H6A1.24900.84780.14580.056*
H6B1.02190.88790.17130.056*
C71.1164 (3)0.6205 (2)0.22548 (6)0.0364 (4)
C81.2736 (3)0.4913 (2)0.24336 (6)0.0376 (4)
C91.2208 (3)0.3953 (2)0.28042 (7)0.0400 (5)
C100.8563 (4)0.5919 (2)0.27273 (7)0.0450 (5)
H100.71260.62390.28420.054*
C110.8987 (4)0.3774 (3)0.33020 (7)0.0511 (5)
H11A0.99460.27270.33650.061*
H11B0.74950.36950.32240.061*
C120.8811 (4)0.4588 (2)0.36991 (7)0.0436 (5)
C131.0709 (4)0.4498 (3)0.39458 (8)0.0593 (6)
H131.21160.39130.38680.071*
C141.0532 (5)0.5267 (4)0.43057 (9)0.0757 (8)
H141.18180.51970.44690.091*
C150.8475 (6)0.6135 (4)0.44248 (9)0.0779 (8)
H150.83650.66610.46670.094*
C160.6579 (5)0.6227 (3)0.41866 (9)0.0712 (8)
H160.51800.68120.42680.085*
C170.6731 (4)0.5455 (3)0.38252 (8)0.0552 (6)
H170.54330.55170.36660.066*
C180.7452 (5)0.1471 (3)0.44535 (8)0.0659 (7)
C190.9630 (5)0.0774 (3)0.43658 (8)0.0661 (7)
H191.08230.08630.45330.079*
C201.0010 (4)0.0071 (3)0.40197 (8)0.0562 (6)
H201.14790.05810.39520.067*
C210.8219 (3)0.0163 (2)0.37733 (7)0.0443 (5)
C220.6101 (4)0.0635 (3)0.38887 (8)0.0640 (7)
H220.48750.06190.37190.077*
C230.8480 (4)0.1146 (3)0.34092 (7)0.0552 (6)
H23A0.87240.22270.35290.066*
H23B0.70770.08590.32440.066*
C241.0343 (3)0.0021 (2)0.27690 (6)0.0372 (4)
C251.2463 (3)0.0436 (2)0.26003 (6)0.0384 (5)
C261.3093 (3)0.0383 (2)0.22143 (6)0.0403 (5)
C270.9221 (4)0.1999 (3)0.22685 (7)0.0471 (5)
H270.81370.28630.21440.057*
C281.1550 (4)0.2696 (3)0.16744 (7)0.0534 (6)
H28A1.31450.26630.16440.064*
H28B1.07440.37560.17110.064*
C291.0716 (4)0.2268 (3)0.12683 (7)0.0484 (5)
C301.2164 (5)0.1361 (3)0.10043 (8)0.0645 (7)
H301.36910.09940.10780.077*
C311.1373 (7)0.0985 (4)0.06286 (9)0.0887 (10)
H311.23680.03690.04530.106*
C320.9140 (8)0.1520 (5)0.05176 (11)0.0997 (12)
H320.86070.12610.02670.120*
C330.7689 (6)0.2435 (5)0.07731 (11)0.0973 (11)
H330.61690.28080.06940.117*
C340.8450 (5)0.2812 (4)0.11462 (9)0.0743 (8)
H340.74420.34370.13180.089*
Cl10.61762 (13)0.64380 (11)0.01849 (2)0.0860 (3)
Cl20.6881 (2)0.25203 (12)0.48969 (3)0.1162 (4)
N10.6569 (3)0.7684 (3)0.08754 (7)0.0709 (7)
N21.2195 (3)0.67680 (19)0.19114 (5)0.0416 (4)
N31.4337 (3)0.5854 (2)0.18785 (6)0.0517 (5)
N41.4664 (3)0.4726 (2)0.21982 (6)0.0489 (4)
N50.9010 (3)0.6798 (2)0.23921 (6)0.0445 (4)
N60.9931 (3)0.45918 (19)0.29311 (5)0.0418 (4)
N71.3390 (3)0.2699 (2)0.30078 (6)0.0523 (5)
H7A1.47580.23240.29290.063*
N80.5685 (4)0.1438 (3)0.42303 (8)0.0766 (7)
N91.0329 (3)0.1005 (2)0.31192 (6)0.0447 (4)
N101.2371 (3)0.2069 (2)0.31669 (6)0.0563 (5)
N111.3668 (3)0.1714 (2)0.28523 (6)0.0524 (5)
N120.8615 (3)0.1264 (2)0.26147 (6)0.0461 (4)
N131.1252 (3)0.1660 (2)0.20643 (5)0.0420 (4)
N141.4930 (3)0.0109 (2)0.20044 (6)0.0561 (5)
H14A1.60300.06660.20980.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0487 (13)0.0755 (16)0.0398 (12)0.0229 (12)0.0053 (10)0.0075 (11)
C20.0539 (15)0.116 (2)0.0602 (17)0.0143 (15)0.0059 (12)0.0445 (16)
C30.0364 (12)0.105 (2)0.0589 (16)0.0132 (13)0.0027 (11)0.0300 (15)
C40.0400 (11)0.0442 (12)0.0372 (11)0.0129 (9)0.0031 (9)0.0012 (9)
C50.0449 (13)0.096 (2)0.0513 (15)0.0035 (13)0.0020 (11)0.0300 (14)
C60.0544 (13)0.0421 (12)0.0446 (12)0.0152 (10)0.0113 (10)0.0008 (10)
C70.0368 (10)0.0358 (10)0.0361 (11)0.0063 (8)0.0076 (8)0.0084 (8)
C80.0349 (10)0.0354 (11)0.0413 (11)0.0049 (8)0.0075 (8)0.0075 (9)
C90.0396 (11)0.0386 (11)0.0424 (11)0.0078 (9)0.0074 (9)0.0105 (9)
C100.0386 (11)0.0459 (12)0.0482 (13)0.0032 (10)0.0027 (9)0.0121 (10)
C110.0552 (13)0.0474 (13)0.0540 (14)0.0194 (11)0.0015 (11)0.0056 (10)
C120.0441 (12)0.0431 (12)0.0432 (12)0.0134 (9)0.0016 (9)0.0015 (9)
C130.0510 (14)0.0684 (16)0.0563 (15)0.0123 (12)0.0047 (11)0.0040 (12)
C140.082 (2)0.099 (2)0.0527 (16)0.0371 (18)0.0139 (14)0.0037 (15)
C150.108 (3)0.087 (2)0.0473 (16)0.0378 (19)0.0141 (16)0.0163 (14)
C160.0766 (19)0.0735 (18)0.0590 (17)0.0124 (15)0.0256 (15)0.0085 (14)
C170.0476 (13)0.0652 (15)0.0502 (14)0.0140 (11)0.0048 (11)0.0021 (12)
C180.083 (2)0.0596 (16)0.0455 (14)0.0034 (14)0.0053 (14)0.0021 (12)
C190.0695 (17)0.0726 (18)0.0566 (16)0.0161 (14)0.0073 (13)0.0118 (13)
C200.0439 (12)0.0642 (15)0.0600 (15)0.0109 (11)0.0012 (11)0.0114 (12)
C210.0418 (11)0.0467 (12)0.0422 (12)0.0116 (10)0.0029 (9)0.0042 (9)
C220.0448 (13)0.0817 (19)0.0572 (16)0.0064 (13)0.0023 (11)0.0039 (14)
C230.0555 (14)0.0672 (16)0.0504 (14)0.0300 (12)0.0049 (11)0.0068 (12)
C240.0353 (10)0.0394 (11)0.0378 (11)0.0076 (9)0.0036 (8)0.0124 (9)
C250.0338 (10)0.0422 (11)0.0386 (11)0.0040 (9)0.0044 (8)0.0141 (9)
C260.0356 (11)0.0485 (12)0.0380 (11)0.0082 (9)0.0052 (9)0.0148 (9)
C270.0425 (12)0.0456 (12)0.0473 (13)0.0019 (10)0.0089 (10)0.0092 (10)
C280.0629 (14)0.0491 (13)0.0512 (14)0.0205 (11)0.0051 (11)0.0036 (11)
C290.0584 (14)0.0481 (13)0.0411 (12)0.0216 (11)0.0037 (10)0.0036 (10)
C300.0801 (18)0.0614 (16)0.0479 (14)0.0142 (14)0.0008 (13)0.0014 (12)
C310.143 (3)0.075 (2)0.0474 (17)0.026 (2)0.0014 (19)0.0092 (14)
C320.155 (4)0.106 (3)0.0534 (19)0.065 (3)0.030 (2)0.0045 (18)
C330.090 (2)0.143 (3)0.068 (2)0.055 (2)0.0297 (19)0.014 (2)
C340.0637 (17)0.103 (2)0.0550 (16)0.0236 (16)0.0086 (13)0.0022 (15)
Cl10.0792 (5)0.1341 (7)0.0573 (4)0.0421 (5)0.0164 (3)0.0258 (4)
Cl20.1700 (10)0.1012 (7)0.0660 (5)0.0061 (6)0.0226 (6)0.0308 (5)
N10.0398 (11)0.1159 (19)0.0575 (13)0.0116 (11)0.0059 (10)0.0288 (13)
N20.0397 (9)0.0416 (10)0.0429 (10)0.0091 (8)0.0082 (8)0.0044 (8)
N30.0401 (10)0.0565 (12)0.0560 (12)0.0094 (9)0.0023 (8)0.0030 (10)
N40.0371 (10)0.0501 (11)0.0552 (12)0.0043 (8)0.0028 (8)0.0034 (9)
N50.0398 (10)0.0439 (10)0.0448 (10)0.0007 (8)0.0054 (8)0.0060 (8)
N60.0426 (10)0.0393 (9)0.0432 (10)0.0086 (8)0.0015 (8)0.0068 (8)
N70.0487 (11)0.0425 (11)0.0587 (12)0.0008 (9)0.0110 (9)0.0006 (9)
N80.0662 (15)0.0866 (17)0.0609 (15)0.0077 (12)0.0152 (12)0.0074 (12)
N90.0426 (10)0.0483 (11)0.0435 (10)0.0101 (8)0.0012 (8)0.0091 (8)
N100.0552 (12)0.0518 (12)0.0534 (12)0.0003 (9)0.0033 (10)0.0013 (9)
N110.0447 (10)0.0541 (12)0.0491 (11)0.0040 (9)0.0029 (9)0.0052 (9)
N120.0349 (9)0.0519 (11)0.0477 (11)0.0017 (8)0.0030 (8)0.0106 (9)
N130.0424 (10)0.0438 (10)0.0391 (10)0.0080 (8)0.0043 (8)0.0077 (8)
N140.0400 (10)0.0775 (14)0.0489 (11)0.0091 (10)0.0025 (9)0.0138 (10)
Geometric parameters (Å, º) top
C1—N11.301 (3)C19—C201.377 (3)
C1—C21.359 (3)C19—H190.9300
C1—Cl11.747 (2)C20—C211.376 (3)
C2—C31.370 (3)C20—H200.9300
C2—H20.9300C21—C221.373 (3)
C3—C41.366 (3)C21—C231.503 (3)
C3—H30.9300C22—N81.343 (3)
C4—C51.363 (3)C22—H220.9300
C4—C61.509 (3)C23—N91.457 (3)
C5—N11.342 (3)C23—H23A0.9700
C5—H50.9300C23—H23B0.9700
C6—N21.459 (3)C24—N91.345 (3)
C6—H6A0.9700C24—C251.370 (3)
C6—H6B0.9700C24—N121.370 (3)
C7—N21.346 (3)C25—N111.360 (3)
C7—C81.368 (3)C25—C261.436 (3)
C7—N51.369 (2)C26—N141.273 (3)
C8—N41.361 (3)C26—N131.423 (3)
C8—C91.441 (3)C27—N121.297 (3)
C9—N71.273 (3)C27—N131.365 (3)
C9—N61.431 (3)C27—H270.9300
C10—N51.302 (3)C28—N131.480 (3)
C10—N61.359 (3)C28—C291.504 (3)
C10—H100.9300C28—H28A0.9700
C11—N61.484 (3)C28—H28B0.9700
C11—C121.503 (3)C29—C301.375 (3)
C11—H11A0.9700C29—C341.389 (3)
C11—H11B0.9700C30—C311.389 (4)
C12—C131.386 (3)C30—H300.9300
C12—C171.386 (3)C31—C321.362 (5)
C13—C141.377 (4)C31—H310.9300
C13—H130.9300C32—C331.362 (5)
C14—C151.369 (4)C32—H320.9300
C14—H140.9300C33—C341.375 (4)
C15—C161.368 (4)C33—H330.9300
C15—H150.9300C34—H340.9300
C16—C171.384 (4)N2—N31.364 (2)
C16—H160.9300N3—N41.313 (3)
C17—H170.9300N7—H7A0.8600
C18—N81.306 (4)N9—N101.361 (2)
C18—C191.356 (4)N10—N111.312 (3)
C18—Cl21.747 (3)N14—H14A0.8600
N1—C1—C2125.0 (2)C20—C21—C23123.2 (2)
N1—C1—Cl1115.55 (17)N8—C22—C21124.3 (2)
C2—C1—Cl1119.48 (19)N8—C22—H22117.9
C1—C2—C3117.7 (2)C21—C22—H22117.9
C1—C2—H2121.2N9—C23—C21114.42 (18)
C3—C2—H2121.2N9—C23—H23A108.7
C4—C3—C2119.9 (2)C21—C23—H23A108.7
C4—C3—H3120.0N9—C23—H23B108.7
C2—C3—H3120.0C21—C23—H23B108.7
C5—C4—C3117.1 (2)H23A—C23—H23B107.6
C5—C4—C6120.9 (2)N9—C24—C25105.25 (17)
C3—C4—C6122.01 (19)N9—C24—N12127.46 (18)
N1—C5—C4124.4 (2)C25—C24—N12127.29 (19)
N1—C5—H5117.8N11—C25—C24108.66 (19)
C4—C5—H5117.8N11—C25—C26130.20 (18)
N2—C6—C4112.29 (17)C24—C25—C26121.13 (18)
N2—C6—H6A109.1N14—C26—N13120.1 (2)
C4—C6—H6A109.1N14—C26—C25130.2 (2)
N2—C6—H6B109.1N13—C26—C25109.74 (17)
C4—C6—H6B109.1N12—C27—N13128.0 (2)
H6A—C6—H6B107.9N12—C27—H27116.0
N2—C7—C8104.89 (17)N13—C27—H27116.0
N2—C7—N5127.29 (18)N13—C28—C29113.43 (18)
C8—C7—N5127.81 (19)N13—C28—H28A108.9
N4—C8—C7109.19 (19)C29—C28—H28A108.9
N4—C8—C9129.66 (18)N13—C28—H28B108.9
C7—C8—C9121.10 (18)C29—C28—H28B108.9
N7—C9—N6120.0 (2)H28A—C28—H28B107.7
N7—C9—C8130.7 (2)C30—C29—C34118.2 (2)
N6—C9—C8109.28 (17)C30—C29—C28121.4 (2)
N5—C10—N6128.2 (2)C34—C29—C28120.4 (2)
N5—C10—H10115.9C29—C30—C31120.8 (3)
N6—C10—H10115.9C29—C30—H30119.6
N6—C11—C12112.68 (17)C31—C30—H30119.6
N6—C11—H11A109.1C32—C31—C30120.0 (3)
C12—C11—H11A109.1C32—C31—H31120.0
N6—C11—H11B109.1C30—C31—H31120.0
C12—C11—H11B109.1C31—C32—C33120.0 (3)
H11A—C11—H11B107.8C31—C32—H32120.0
C13—C12—C17118.5 (2)C33—C32—H32120.0
C13—C12—C11121.1 (2)C32—C33—C34120.6 (3)
C17—C12—C11120.4 (2)C32—C33—H33119.7
C14—C13—C12120.6 (2)C34—C33—H33119.7
C14—C13—H13119.7C33—C34—C29120.5 (3)
C12—C13—H13119.7C33—C34—H34119.8
C15—C14—C13120.5 (3)C29—C34—H34119.8
C15—C14—H14119.8C1—N1—C5116.0 (2)
C13—C14—H14119.8C7—N2—N3110.05 (16)
C16—C15—C14119.7 (3)C7—N2—C6129.13 (17)
C16—C15—H15120.1N3—N2—C6120.61 (18)
C14—C15—H15120.1N4—N3—N2107.70 (17)
C15—C16—C17120.5 (3)N3—N4—C8108.16 (16)
C15—C16—H16119.8C10—N5—C7110.24 (17)
C17—C16—H16119.8C10—N6—C9123.29 (18)
C16—C17—C12120.2 (2)C10—N6—C11117.72 (18)
C16—C17—H17119.9C9—N6—C11118.99 (17)
C12—C17—H17119.9C9—N7—H7A119.3
N8—C18—C19125.3 (2)C18—N8—C22116.1 (2)
N8—C18—Cl2115.6 (2)C24—N9—N10109.90 (17)
C19—C18—Cl2119.1 (2)C24—N9—C23129.50 (19)
C18—C19—C20117.4 (3)N10—N9—C23120.47 (19)
C18—C19—H19121.3N11—N10—N9107.71 (17)
C20—C19—H19121.3N10—N11—C25108.47 (17)
C21—C20—C19120.1 (2)C27—N12—C24110.74 (18)
C21—C20—H20119.9C27—N13—C26123.09 (18)
C19—C20—H20119.9C27—N13—C28117.92 (18)
C22—C21—C20116.6 (2)C26—N13—C28118.98 (18)
C22—C21—C23120.0 (2)C26—N14—H14A119.2
N1—C1—C2—C30.6 (5)C30—C29—C34—C330.6 (4)
Cl1—C1—C2—C3179.4 (2)C28—C29—C34—C33179.4 (3)
C1—C2—C3—C40.7 (5)C2—C1—N1—C50.7 (4)
C2—C3—C4—C50.9 (4)Cl1—C1—N1—C5179.6 (2)
C2—C3—C4—C6177.7 (3)C4—C5—N1—C11.0 (4)
C3—C4—C5—N11.1 (4)C8—C7—N2—N30.0 (2)
C6—C4—C5—N1177.6 (2)N5—C7—N2—N3179.75 (18)
C5—C4—C6—N2107.6 (3)C8—C7—N2—C6174.65 (18)
C3—C4—C6—N273.8 (3)N5—C7—N2—C65.1 (3)
N2—C7—C8—N40.2 (2)C4—C6—N2—C784.0 (3)
N5—C7—C8—N4179.92 (18)C4—C6—N2—N390.1 (2)
N2—C7—C8—C9177.67 (17)C7—N2—N3—N40.2 (2)
N5—C7—C8—C92.1 (3)C6—N2—N3—N4175.36 (17)
N4—C8—C9—N70.4 (4)N2—N3—N4—C80.3 (2)
C7—C8—C9—N7177.7 (2)C7—C8—N4—N30.3 (2)
N4—C8—C9—N6177.81 (19)C9—C8—N4—N3177.32 (19)
C7—C8—C9—N60.5 (2)N6—C10—N5—C70.0 (3)
N6—C11—C12—C1376.1 (3)N2—C7—N5—C10177.90 (19)
N6—C11—C12—C17103.6 (2)C8—C7—N5—C101.8 (3)
C17—C12—C13—C140.7 (4)N5—C10—N6—C91.5 (3)
C11—C12—C13—C14179.1 (2)N5—C10—N6—C11178.2 (2)
C12—C13—C14—C150.1 (4)N7—C9—N6—C10179.51 (19)
C13—C14—C15—C160.6 (4)C8—C9—N6—C101.1 (2)
C14—C15—C16—C170.3 (4)N7—C9—N6—C110.2 (3)
C15—C16—C17—C120.5 (4)C8—C9—N6—C11178.59 (16)
C13—C12—C17—C160.9 (3)C12—C11—N6—C1074.6 (2)
C11—C12—C17—C16178.8 (2)C12—C11—N6—C9105.7 (2)
N8—C18—C19—C201.8 (4)C19—C18—N8—C220.3 (4)
Cl2—C18—C19—C20178.6 (2)Cl2—C18—N8—C22180.0 (2)
C18—C19—C20—C211.1 (4)C21—C22—N8—C181.9 (4)
C19—C20—C21—C220.8 (4)C25—C24—N9—N100.1 (2)
C19—C20—C21—C23175.9 (2)N12—C24—N9—N10179.77 (19)
C20—C21—C22—N82.4 (4)C25—C24—N9—C23175.82 (19)
C23—C21—C22—N8174.4 (2)N12—C24—N9—C234.5 (3)
C22—C21—C23—N9137.4 (2)C21—C23—N9—C2487.3 (3)
C20—C21—C23—N946.0 (3)C21—C23—N9—N1097.4 (2)
N9—C24—C25—N110.2 (2)C24—N9—N10—N110.4 (2)
N12—C24—C25—N11179.42 (19)C23—N9—N10—N11176.60 (18)
N9—C24—C25—C26178.91 (17)N9—N10—N11—C250.6 (2)
N12—C24—C25—C261.4 (3)C24—C25—N11—N100.5 (2)
N11—C25—C26—N141.3 (4)C26—C25—N11—N10178.5 (2)
C24—C25—C26—N14177.6 (2)N13—C27—N12—C240.2 (3)
N11—C25—C26—N13179.98 (19)N9—C24—N12—C27179.68 (19)
C24—C25—C26—N131.0 (2)C25—C24—N12—C270.7 (3)
N13—C28—C29—C3096.1 (3)N12—C27—N13—C260.4 (3)
N13—C28—C29—C3485.2 (3)N12—C27—N13—C28179.0 (2)
C34—C29—C30—C310.7 (4)N14—C26—N13—C27178.57 (19)
C28—C29—C30—C31179.5 (2)C25—C26—N13—C270.2 (3)
C29—C30—C31—C320.1 (4)N14—C26—N13—C282.8 (3)
C30—C31—C32—C330.6 (5)C25—C26—N13—C28178.38 (16)
C31—C32—C33—C340.7 (5)C29—C28—N13—C2786.0 (2)
C32—C33—C34—C290.1 (5)C29—C28—N13—C2695.4 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of the N2–N4/C8/C7 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N14—H14A···N5i0.862.603.457 (3)173
N7—H7A···N12ii0.862.533.389 (3)174
C5—H5···N14iii0.932.583.506 (3)177
C10—H10···N11iii0.932.423.240 (3)147
C27—H27···N4iv0.932.363.191 (3)149
C23—H23A···Cg4v0.972.583.509 (3)160
C28—H28B···Cg10.972.933.506 (3)120
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y, z; (iii) x1, y+1, z; (iv) x1, y, z; (v) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H14ClN7
Mr351.80
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.1090 (7), 8.9537 (11), 31.292 (4)
α, β, γ (°)83.141 (1), 88.896 (1), 75.184 (1)
V3)1642.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.47 × 0.39 × 0.21
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.892, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
12520, 6071, 4578
Rint0.018
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.123, 1.03
No. of reflections6071
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.52

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of the N2–N4/C8/C7 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N14—H14A···N5i0.862.603.457 (3)173.3
N7—H7A···N12ii0.862.533.389 (3)173.7
C5—H5···N14iii0.932.583.506 (3)177
C10—H10···N11iii0.932.423.240 (3)147
C27—H27···N4iv0.932.363.191 (3)149
C23—H23A···Cg4v0.972.583.509 (3)160
C28—H28B···Cg10.972.933.506 (3)120
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y, z; (iii) x1, y+1, z; (iv) x1, y, z; (v) x, y1, z.
 

Acknowledgements

The authors are grateful to the Hubei University of Medicine Education Committee (grant No. 2009QJ12) for financial support and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Whuhan, for the data collection.

References

First citationBruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSantana, L., Teijeira, M., Uriarte, E., Balzarini, J. & De Clercq, E. (2002). Eur. J. Med. Chem. 37, 755–760.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, J. F., Xie, C., Ding, M. W. & He, H. W. (2005). Synthesis, 15, 2544–2549.  Google Scholar

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