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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 2| February 2011| Page o312
doi:10.1107/S1600536811000584

2-Chloro-4,6-bis­­(piperidin-1-yl)-1,3,5-triazine

Jasmine P. Vennila,a D. John Thiruvadigal,b Helen P. Kavitha,c G. Chakkaravarthid and V. Manivannane*

aDepartment of Physics, Panimalar Institute of Technology, Chennai 602 103, India, bDepartment of Physics, SRM University, Kattankulathur Campus, Chennai, India, cDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com

(Received 15 December 2010; accepted 5 January 2011; online 8 January 2011)

The title compound, C13H20ClN5, crystallizes with two mol­ecules in the asymmetric unit. The piperidine rings in both mol­ecules adopt chair conformations. Weak π–π inter­actions [centroid–centroid distance = 3.9815 (8) Å] are observed in the crystal structure.

Related literature

For the biological activity of related compounds, see: Azev et al. (2003[Azev, Y. A., Dulcks, T. & Gabel, D. (2003). Tetrahedron Lett. 44, 8689-8691.]); Steffensen & Simanek (2003[Steffensen, M. B. & Simanek, E. E. (2003). Org. Lett. 5, 2359-2361.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C13H20ClN5

  • Mr = 281.79

  • Triclinic, [P \overline 1]

  • a = 10.5085 (2) Å

  • b = 11.7016 (3) Å

  • c = 12.6086 (3) Å

  • α = 89.813 (1)°

  • β = 67.967 (2)°

  • γ = 81.627 (1)°

  • V = 1419.65 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 295 K

  • 0.22 × 0.18 × 0.16 mm
Data collection

  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.944, Tmax = 0.959

  • 41337 measured reflections

  • 11234 independent reflections

  • 5899 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.140

  • S = 1.02

  • 11234 reflections

  • 343 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000584/im2259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000584/im2259Isup2.hkl

checkCIF report


Comment top

1,3,5-Triazine derivatives are of great interest due to their importance as starting materials for drugs and light stabilizers (Azev et al., 2003; Steffensen & Simanek, 2003). In the structure of the title compound (Fig. 1), all bond lengths and angles are in agreement with literature values (Allen et al., 1987).

The piperidine rings N1/C1—C5, N5/C9—C13, N6/C22—C26 and N10/C14—C18 adopt chair conformation [Puckering parameters as defined by Cremer & Pople, 1975: Q = 0.548 (2) Å, θ = 178.3 (2)°, ϕ = 301 (7)° for the ring N1/C1—C5; Q = 0.555 (2) Å, θ = 179.1 (2)°, ϕ = 67 (2)° for the ring N5/C9—C13; Q = 0.551 (2) Å, θ = 180.0 (2)°, ϕ = 161 (3)° for the ring N6/C22—C26; Q = 0.547 (2) Å, θ = 178.7 (2)°, ϕ = 355 (8)° for the ring N10/C14—C18].

The molecular structure is stabilized by the weak intramolecular C—H···N hydrogen bonds [Table 1] and the crystal structure is stabilized by weak π–π interaction [Cg2···Cg5 (1 + x,y,z) distance of 3.9815 (8) Å; Cg2 and Cg5 are the centroids of the rings (N2/C6/N4/C8/N3/C7) and (N7/C20/N8/C19/N9/C21), respectively].

Related literature top

For the biological activity of related compounds, see: Azev et al. (2003); Steffensen & Simanek (2003). For bond-length data, see: Allen et al. (1987). For puckering and asymmetry parameters, see: Cremer & Pople (1975).

Experimental top

To a stirred solution of piperidine (1 ml) in dichloromethane (10 ml) at 0°C under argon, was added a solution of cyanuric chloride (1.85 g, 10 mmol) in CH2Cl2 (6 ml) and the reaction mixture was allowed to warm to room temperature. After 14 h, the mixture was partitioned between CH2Cl2 (20 ml) and saturated aqueous sodium chloride (50 ml). The aqueous phase was extracted with CH2Cl2 (50 ml), the combined organic layer was dried (MgSO4), filtered, evaporated to dryness and purified by recrystallization with ethanol to yield colourless diffraction quality crystals (yield: 68%).

Refinement top

H atoms were positioned geometrically with C—H = 0.97 Å and refined using riding-model approximation with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
2-Chloro-4,6-bis(piperidin-1-yl)-1,3,5-triazine top
Crystal data top
C13H20ClN5Z = 4
Mr = 281.79F(000) = 600
Triclinic, P1Dx = 1.318 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5085 (2) ÅCell parameters from 9620 reflections
b = 11.7016 (3) Åθ = 2.2–27.3°
c = 12.6086 (3) ŵ = 0.26 mm−1
α = 89.813 (1)°T = 295 K
β = 67.967 (2)°Block, colourless
γ = 81.627 (1)°0.22 × 0.18 × 0.16 mm
V = 1419.65 (6) Å3
Data collection top
Bruker Kappa APEXII
diffractometer		11234 independent reflections
Radiation source: fine-focus sealed tube5899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and ϕ scansθmax = 33.8°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→15
Tmin = 0.944, Tmax = 0.959k = −18→18
41337 measured reflectionsl = −19→19
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1529P]
where P = (Fo2 + 2Fc2)/3
11234 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C13H20ClN5γ = 81.627 (1)°
Mr = 281.79V = 1419.65 (6) Å3
Triclinic, P1Z = 4
a = 10.5085 (2) ÅMo Kα radiation
b = 11.7016 (3) ŵ = 0.26 mm−1
c = 12.6086 (3) ÅT = 295 K
α = 89.813 (1)°0.22 × 0.18 × 0.16 mm
β = 67.967 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer		11234 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5899 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.959Rint = 0.030
41337 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.02Δρmax = 0.22 e Å−3
11234 reflectionsΔρmin = −0.24 e Å−3
343 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.70319 (4)−0.10443 (3)0.75663 (3)0.05514 (11)
Cl2−0.24596 (4)0.58017 (3)0.75933 (3)0.06773 (13)
N10.40712 (12)0.27129 (10)0.86606 (10)0.0511 (3)
N20.60248 (11)0.26026 (9)0.70082 (9)0.0445 (3)
N30.75188 (11)0.07769 (9)0.64173 (9)0.0439 (2)
N40.54969 (11)0.09552 (9)0.81220 (9)0.0428 (2)
N50.80109 (13)0.23811 (11)0.53713 (10)0.0570 (3)
N6−0.25057 (13)0.21549 (11)0.94787 (10)0.0574 (3)
N7−0.24388 (11)0.38829 (10)0.85973 (9)0.0470 (3)
N8−0.04785 (11)0.40643 (9)0.69089 (9)0.0460 (3)
N9−0.05891 (11)0.22899 (9)0.78582 (9)0.0430 (2)
N100.12982 (12)0.25155 (9)0.62450 (10)0.0492 (3)
C10.31252 (14)0.22201 (13)0.96503 (12)0.0534 (4)
H1A0.31360.25621.03460.064*
H1B0.34290.13940.96250.064*
C20.16681 (16)0.24390 (14)0.96658 (15)0.0615 (4)
H2A0.10400.21511.03580.074*
H2B0.16380.20240.90130.074*
C30.11979 (17)0.37162 (14)0.96222 (15)0.0659 (4)
H3A0.11120.41201.03220.079*
H3B0.02930.38320.95660.079*
C40.22327 (18)0.42082 (14)0.85997 (14)0.0690 (5)
H4A0.22160.38820.79000.083*
H4B0.19620.50390.86250.083*
C50.36840 (17)0.39485 (12)0.85844 (14)0.0615 (4)
H5A0.43300.42040.78820.074*
H5B0.37370.43690.92240.074*
C60.52309 (13)0.20869 (11)0.79053 (11)0.0404 (3)
C70.71608 (13)0.19218 (11)0.62899 (11)0.0418 (3)
C80.66359 (12)0.04159 (10)0.73336 (11)0.0388 (3)
C90.77292 (19)0.35800 (13)0.51028 (13)0.0637 (4)
H9A0.84750.39840.50970.076*
H9B0.68710.39600.56880.076*
C100.76069 (17)0.36363 (13)0.39468 (13)0.0612 (4)
H10A0.67880.33220.39830.073*
H10B0.74990.44370.37500.073*
C110.88763 (17)0.29627 (15)0.30323 (13)0.0624 (4)
H11A0.96770.33390.29230.075*
H11B0.87400.29520.23130.075*
C120.91444 (15)0.17377 (14)0.33667 (13)0.0583 (4)
H12A0.83940.13340.33840.070*
H12B1.00010.13360.27970.070*
C130.92525 (14)0.17194 (15)0.45222 (12)0.0562 (4)
H13A0.93620.09270.47420.067*
H13B1.00630.20480.44860.067*
C140.18931 (16)0.12999 (12)0.62002 (13)0.0565 (4)
H14A0.18270.08880.55610.068*
H14B0.13710.09540.68990.068*
C150.33961 (17)0.11873 (14)0.60639 (14)0.0640 (4)
H15A0.34500.15130.67500.077*
H15B0.37940.03750.59740.077*
C160.42257 (15)0.17999 (14)0.50403 (14)0.0610 (4)
H16A0.42710.14160.43440.073*
H16B0.51660.17670.50100.073*
C170.35592 (15)0.30484 (14)0.51179 (14)0.0601 (4)
H17A0.36210.34540.57620.072*
H17B0.40600.34150.44260.072*
C180.20574 (14)0.31413 (13)0.52655 (12)0.0521 (3)
H18A0.16380.39490.53780.063*
H18B0.19990.28260.45770.063*
C190.00440 (13)0.29585 (10)0.70277 (10)0.0396 (3)
C20−0.16935 (14)0.44079 (11)0.77202 (11)0.0440 (3)
C21−0.18221 (13)0.27845 (11)0.86233 (11)0.0430 (3)
C22−0.38604 (14)0.25932 (15)1.03571 (13)0.0594 (4)
H22A−0.45440.21401.03140.071*
H22B−0.41470.33901.02270.071*
C23−0.37895 (16)0.25251 (15)1.15248 (13)0.0607 (4)
H23A−0.47110.27581.21050.073*
H23B−0.31960.30561.15990.073*
C24−0.32291 (16)0.13175 (15)1.17191 (13)0.0605 (4)
H24A−0.38880.08051.17520.073*
H24B−0.31160.13141.24480.073*
C25−0.18487 (15)0.08791 (14)1.07732 (14)0.0586 (4)
H25A−0.11560.13261.08080.070*
H25B−0.15530.00781.08810.070*
C26−0.19536 (17)0.09730 (13)0.96164 (13)0.0616 (4)
H26A−0.10410.07490.90190.074*
H26B−0.25580.04520.95440.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0520 (2)0.04075 (19)0.0592 (2)0.00433 (14)−0.01014 (16)0.00949 (15)
Cl20.0742 (3)0.0482 (2)0.0646 (3)0.01757 (18)−0.0179 (2)0.00811 (18)
N10.0514 (6)0.0375 (6)0.0469 (6)0.0045 (5)−0.0031 (5)0.0045 (5)
N20.0512 (6)0.0386 (6)0.0376 (6)−0.0052 (5)−0.0105 (5)0.0023 (5)
N30.0423 (6)0.0431 (6)0.0395 (6)−0.0031 (5)−0.0092 (5)0.0041 (5)
N40.0420 (6)0.0381 (6)0.0409 (6)−0.0006 (4)−0.0095 (5)0.0057 (5)
N50.0596 (7)0.0488 (7)0.0466 (7)−0.0069 (6)−0.0025 (6)0.0104 (5)
N60.0514 (7)0.0514 (7)0.0510 (7)0.0000 (5)−0.0017 (6)0.0114 (6)
N70.0456 (6)0.0464 (6)0.0432 (6)0.0032 (5)−0.0140 (5)0.0030 (5)
N80.0491 (6)0.0381 (6)0.0439 (6)0.0004 (5)−0.0125 (5)0.0053 (5)
N90.0442 (6)0.0380 (6)0.0401 (6)−0.0026 (5)−0.0098 (5)0.0031 (5)
N100.0464 (6)0.0375 (6)0.0482 (7)−0.0009 (5)−0.0023 (5)0.0069 (5)
C10.0510 (8)0.0489 (8)0.0439 (8)0.0047 (6)−0.0042 (6)0.0076 (6)
C20.0512 (8)0.0541 (9)0.0659 (10)−0.0005 (7)−0.0100 (7)−0.0025 (8)
C30.0541 (9)0.0586 (10)0.0753 (11)0.0103 (7)−0.0205 (8)−0.0064 (8)
C40.0862 (12)0.0459 (9)0.0638 (10)0.0182 (8)−0.0262 (9)−0.0009 (7)
C50.0666 (10)0.0371 (8)0.0593 (9)0.0024 (7)−0.0034 (8)0.0018 (7)
C60.0438 (6)0.0370 (6)0.0369 (6)−0.0024 (5)−0.0128 (5)0.0016 (5)
C70.0450 (7)0.0417 (7)0.0376 (7)−0.0086 (5)−0.0139 (6)0.0035 (5)
C80.0391 (6)0.0366 (6)0.0395 (7)−0.0016 (5)−0.0150 (5)0.0024 (5)
C90.0852 (11)0.0450 (8)0.0488 (9)−0.0179 (8)−0.0090 (8)0.0100 (7)
C100.0726 (10)0.0467 (8)0.0640 (10)−0.0146 (7)−0.0237 (8)0.0136 (7)
C110.0685 (10)0.0742 (11)0.0474 (9)−0.0218 (8)−0.0213 (8)0.0113 (8)
C120.0466 (8)0.0683 (10)0.0529 (9)−0.0049 (7)−0.0122 (7)−0.0012 (7)
C130.0401 (7)0.0713 (10)0.0491 (8)−0.0091 (7)−0.0076 (6)0.0127 (7)
C140.0594 (9)0.0359 (7)0.0556 (9)0.0022 (6)−0.0043 (7)0.0030 (6)
C150.0658 (10)0.0557 (9)0.0587 (9)0.0145 (7)−0.0188 (8)−0.0019 (7)
C160.0459 (8)0.0655 (10)0.0610 (10)0.0016 (7)−0.0120 (7)−0.0065 (8)
C170.0532 (8)0.0596 (10)0.0573 (9)−0.0124 (7)−0.0080 (7)−0.0017 (7)
C180.0517 (8)0.0460 (8)0.0479 (8)−0.0044 (6)−0.0079 (6)0.0086 (6)
C190.0429 (6)0.0342 (6)0.0394 (7)−0.0029 (5)−0.0141 (5)0.0003 (5)
C200.0500 (7)0.0381 (7)0.0429 (7)0.0027 (6)−0.0198 (6)0.0007 (5)
C210.0440 (7)0.0445 (7)0.0391 (7)−0.0056 (6)−0.0148 (6)0.0030 (6)
C220.0405 (7)0.0726 (10)0.0549 (9)−0.0043 (7)−0.0082 (6)0.0140 (8)
C230.0446 (8)0.0743 (11)0.0539 (9)−0.0044 (7)−0.0098 (7)−0.0004 (8)
C240.0536 (8)0.0775 (11)0.0532 (9)−0.0152 (8)−0.0215 (7)0.0146 (8)
C250.0494 (8)0.0528 (9)0.0723 (10)−0.0111 (7)−0.0206 (8)0.0158 (7)
C260.0676 (10)0.0442 (8)0.0569 (9)−0.0082 (7)−0.0057 (8)0.0099 (7)
Geometric parameters (Å, º) top
Cl1—C81.7493 (12)C9—H9A0.9700
Cl2—C201.7454 (12)C9—H9B0.9700
N1—C61.3426 (16)C10—C111.509 (2)
N1—C11.4523 (18)C10—H10A0.9700
N1—C51.4569 (17)C10—H10B0.9700
N2—C61.3318 (16)C11—C121.510 (2)
N2—C71.3403 (16)C11—H11A0.9700
N3—C81.2964 (16)C11—H11B0.9700
N3—C71.3637 (16)C12—C131.503 (2)
N4—C81.3078 (15)C12—H12A0.9700
N4—C61.3615 (16)C12—H12B0.9700
N5—C71.3371 (17)C13—H13A0.9700
N5—C131.4530 (18)C13—H13B0.9700
N5—C91.4565 (18)C14—C151.509 (2)
N6—C211.3378 (17)C14—H14A0.9700
N6—C261.4559 (18)C14—H14B0.9700
N6—C221.4575 (18)C15—C161.507 (2)
N7—C201.3037 (17)C15—H15A0.9700
N7—C211.3587 (16)C15—H15B0.9700
N8—C201.3082 (17)C16—C171.512 (2)
N8—C191.3607 (15)C16—H16A0.9700
N9—C191.3323 (16)C16—H16B0.9700
N9—C211.3386 (16)C17—C181.506 (2)
N10—C191.3447 (16)C17—H17A0.9700
N10—C181.4571 (17)C17—H17B0.9700
N10—C141.4602 (16)C18—H18A0.9700
C1—C21.508 (2)C18—H18B0.9700
C1—H1A0.9700C22—C231.503 (2)
C1—H1B0.9700C22—H22A0.9700
C2—C31.512 (2)C22—H22B0.9700
C2—H2A0.9700C23—C241.506 (2)
C2—H2B0.9700C23—H23A0.9700
C3—C41.517 (2)C23—H23B0.9700
C3—H3A0.9700C24—C251.510 (2)
C3—H3B0.9700C24—H24A0.9700
C4—C51.504 (2)C24—H24B0.9700
C4—H4A0.9700C25—C261.506 (2)
C4—H4B0.9700C25—H25A0.9700
C5—H5A0.9700C25—H25B0.9700
C5—H5B0.9700C26—H26A0.9700
C9—C101.511 (2)C26—H26B0.9700
C6—N1—C1122.56 (11)C13—C12—H12B109.4
C6—N1—C5123.04 (11)C11—C12—H12B109.4
C1—N1—C5114.37 (11)H12A—C12—H12B108.0
C6—N2—C7115.16 (11)N5—C13—C12110.02 (12)
C8—N3—C7112.00 (11)N5—C13—H13A109.7
C8—N4—C6111.91 (11)C12—C13—H13A109.7
C7—N5—C13123.28 (12)N5—C13—H13B109.7
C7—N5—C9122.63 (12)C12—C13—H13B109.7
C13—N5—C9114.01 (12)H13A—C13—H13B108.2
C21—N6—C26122.78 (12)N10—C14—C15110.52 (13)
C21—N6—C22123.04 (12)N10—C14—H14A109.5
C26—N6—C22114.18 (12)C15—C14—H14A109.5
C20—N7—C21111.92 (11)N10—C14—H14B109.5
C20—N8—C19111.78 (11)C15—C14—H14B109.5
C19—N9—C21115.25 (11)H14A—C14—H14B108.1
C19—N10—C18122.92 (11)C16—C15—C14111.44 (13)
C19—N10—C14122.06 (11)C16—C15—H15A109.3
C18—N10—C14114.21 (11)C14—C15—H15A109.3
N1—C1—C2110.51 (12)C16—C15—H15B109.3
N1—C1—H1A109.5C14—C15—H15B109.3
C2—C1—H1A109.5H15A—C15—H15B108.0
N1—C1—H1B109.5C15—C16—C17110.23 (12)
C2—C1—H1B109.5C15—C16—H16A109.6
H1A—C1—H1B108.1C17—C16—H16A109.6
C1—C2—C3110.93 (13)C15—C16—H16B109.6
C1—C2—H2A109.5C17—C16—H16B109.6
C3—C2—H2A109.5H16A—C16—H16B108.1
C1—C2—H2B109.5C18—C17—C16111.37 (13)
C3—C2—H2B109.5C18—C17—H17A109.4
H2A—C2—H2B108.0C16—C17—H17A109.4
C2—C3—C4110.40 (12)C18—C17—H17B109.4
C2—C3—H3A109.6C16—C17—H17B109.4
C4—C3—H3A109.6H17A—C17—H17B108.0
C2—C3—H3B109.6N10—C18—C17110.78 (12)
C4—C3—H3B109.6N10—C18—H18A109.5
H3A—C3—H3B108.1C17—C18—H18A109.5
C5—C4—C3111.71 (13)N10—C18—H18B109.5
C5—C4—H4A109.3C17—C18—H18B109.5
C3—C4—H4A109.3H18A—C18—H18B108.1
C5—C4—H4B109.3N9—C19—N10117.95 (11)
C3—C4—H4B109.3N9—C19—N8125.01 (11)
H4A—C4—H4B107.9N10—C19—N8117.03 (11)
N1—C5—C4110.60 (13)N7—C20—N8131.13 (12)
N1—C5—H5A109.5N7—C20—Cl2114.49 (10)
C4—C5—H5A109.5N8—C20—Cl2114.38 (10)
N1—C5—H5B109.5N6—C21—N9117.93 (12)
C4—C5—H5B109.5N6—C21—N7117.19 (12)
H5A—C5—H5B108.1N9—C21—N7124.89 (12)
N2—C6—N1118.59 (11)N6—C22—C23110.09 (12)
N2—C6—N4124.96 (11)N6—C22—H22A109.6
N1—C6—N4116.45 (11)C23—C22—H22A109.6
N5—C7—N2118.54 (12)N6—C22—H22B109.6
N5—C7—N3116.69 (12)C23—C22—H22B109.6
N2—C7—N3124.76 (11)H22A—C22—H22B108.2
N3—C8—N4131.21 (12)C22—C23—C24111.25 (13)
N3—C8—Cl1114.80 (9)C22—C23—H23A109.4
N4—C8—Cl1113.99 (9)C24—C23—H23A109.4
N5—C9—C10110.38 (12)C22—C23—H23B109.4
N5—C9—H9A109.6C24—C23—H23B109.4
C10—C9—H9A109.6H23A—C23—H23B108.0
N5—C9—H9B109.6C23—C24—C25111.13 (13)
C10—C9—H9B109.6C23—C24—H24A109.4
H9A—C9—H9B108.1C25—C24—H24A109.4
C11—C10—C9110.94 (14)C23—C24—H24B109.4
C11—C10—H10A109.5C25—C24—H24B109.4
C9—C10—H10A109.5H24A—C24—H24B108.0
C11—C10—H10B109.5C26—C25—C24110.94 (12)
C9—C10—H10B109.5C26—C25—H25A109.5
H10A—C10—H10B108.0C24—C25—H25A109.5
C10—C11—C12110.62 (13)C26—C25—H25B109.5
C10—C11—H11A109.5C24—C25—H25B109.5
C12—C11—H11A109.5H25A—C25—H25B108.0
C10—C11—H11B109.5N6—C26—C25110.16 (13)
C12—C11—H11B109.5N6—C26—H26A109.6
H11A—C11—H11B108.1C25—C26—H26A109.6
C13—C12—C11111.11 (13)N6—C26—H26B109.6
C13—C12—H12A109.4C25—C26—H26B109.6
C11—C12—H12A109.4H26A—C26—H26B108.1
C6—N1—C1—C2−125.43 (14)C19—N10—C14—C15−134.48 (14)
C5—N1—C1—C256.89 (17)C18—N10—C14—C1555.57 (17)
N1—C1—C2—C3−55.30 (17)N10—C14—C15—C16−54.49 (17)
C1—C2—C3—C454.33 (18)C14—C15—C16—C1754.67 (18)
C2—C3—C4—C5−53.65 (19)C15—C16—C17—C18−54.55 (18)
C6—N1—C5—C4126.52 (15)C19—N10—C18—C17134.52 (14)
C1—N1—C5—C4−55.82 (17)C14—N10—C18—C17−55.63 (17)
C3—C4—C5—N153.34 (18)C16—C17—C18—N1054.34 (17)
C7—N2—C6—N1−179.74 (11)C21—N9—C19—N10178.84 (11)
C7—N2—C6—N4−0.14 (19)C21—N9—C19—N8−0.91 (19)
C1—N1—C6—N2178.59 (12)C18—N10—C19—N9176.73 (12)
C5—N1—C6—N2−3.9 (2)C14—N10—C19—N97.66 (19)
C1—N1—C6—N4−1.0 (2)C18—N10—C19—N8−3.49 (19)
C5—N1—C6—N4176.42 (12)C14—N10—C19—N8−172.56 (12)
C8—N4—C6—N2−0.39 (18)C20—N8—C19—N90.31 (18)
C8—N4—C6—N1179.22 (11)C20—N8—C19—N10−179.44 (11)
C13—N5—C7—N2−178.52 (12)C21—N7—C20—N8−1.7 (2)
C9—N5—C7—N2−1.9 (2)C21—N7—C20—Cl2177.15 (9)
C13—N5—C7—N30.9 (2)C19—N8—C20—N71.2 (2)
C9—N5—C7—N3177.51 (13)C19—N8—C20—Cl2−177.71 (9)
C6—N2—C7—N5−179.76 (12)C26—N6—C21—N91.0 (2)
C6—N2—C7—N30.87 (19)C22—N6—C21—N9−179.42 (13)
C8—N3—C7—N5179.68 (11)C26—N6—C21—N7−179.10 (13)
C8—N3—C7—N2−0.93 (18)C22—N6—C21—N70.5 (2)
C7—N3—C8—N40.3 (2)C19—N9—C21—N6−179.88 (12)
C7—N3—C8—Cl1−179.40 (9)C19—N9—C21—N70.25 (19)
C6—N4—C8—N30.3 (2)C20—N7—C21—N6−178.97 (12)
C6—N4—C8—Cl1−179.99 (8)C20—N7—C21—N90.90 (19)
C7—N5—C9—C10−119.80 (16)C21—N6—C22—C23−122.32 (16)
C13—N5—C9—C1057.09 (18)C26—N6—C22—C2357.27 (18)
N5—C9—C10—C11−54.29 (18)N6—C22—C23—C24−54.38 (18)
C9—C10—C11—C1254.06 (17)C22—C23—C24—C2553.98 (17)
C10—C11—C12—C13−54.84 (17)C23—C24—C25—C26−53.93 (18)
C7—N5—C13—C12119.29 (15)C21—N6—C26—C25122.17 (15)
C9—N5—C13—C12−57.58 (18)C22—N6—C26—C25−57.43 (18)
C11—C12—C13—N555.47 (17)C24—C25—C26—N654.50 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···N20.972.322.7637 (18)107
C13—H13A···N30.972.302.7472 (17)107
C14—H14B···N90.972.312.7497 (18)106
C18—H18A···N80.972.322.7560 (18)106
C22—H22B···N70.972.302.7532 (19)107
C26—H26A···N90.972.312.7534 (18)107

Experimental details

Crystal data
Chemical formulaC13H20ClN5
Mr281.79
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)10.5085 (2), 11.7016 (3), 12.6086 (3)
α, β, γ (°)89.813 (1), 67.967 (2), 81.627 (1)
V (Å3)1419.65 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.26
Crystal size (mm)0.22 × 0.18 × 0.16
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.944, 0.959
No. of measured, independent and
observed [I > 2σ(I)] reflections		41337, 11234, 5899
Rint0.030
(sin θ/λ)max (Å−1)0.783
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.140, 1.02
No. of reflections11234
No. of parameters343
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.24

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···N20.972.322.7637 (18)107
C13—H13A···N30.972.302.7472 (17)107
C14—H14B···N90.972.312.7497 (18)106
C18—H18A···N80.972.322.7560 (18)106
C22—H22B···N70.972.302.7532 (19)107
C26—H26A···N90.972.312.7534 (18)107
 

Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationAzev, Y. A., Dulcks, T. & Gabel, D. (2003). Tetrahedron Lett. 44, 8689–8691.  Web of Science CrossRef CAS Google Scholar
 First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (1996). 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 citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSteffensen, M. B. & Simanek, E. E. (2003). Org. Lett. 5, 2359–2361.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 67| Part 2| February 2011| Page o312
doi:10.1107/S1600536811000584
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