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Acta Cryst. (2011). E67, o312    [ doi:10.1107/S1600536811000584 ]

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

J. P. Vennila, D. J. Thiruvadigal, H. P. Kavitha, G. Chakkaravarthi and V. Manivannan

Abstract top

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

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)
graphiteRint = 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		5899 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.030
Tmin = 0.944, Tmax = 0.959θmax = 33.8°
41337 measured reflectionsStandard reflections: 0
11234 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.140Δρmax = 0.22 e Å−3
S = 1.02Δρmin = −0.24 e Å−3
11234 reflectionsAbsolute structure: ?
343 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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, °) 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, °) 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
Table 1
Hydrogen-bond geometry (Å, °) 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 top

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

references
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