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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jan 8;67(Pt 2):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 Chakkaravarthi d, V Manivannan e,*
PMCID: PMC3051665  PMID: 21523000

Abstract

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 ▶); Steffensen & Simanek (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶).graphic file with name e-67-0o312-scheme1.jpg

Experimental

Crystal data

  • C13H20ClN5

  • M r = 281.79

  • Triclinic, Inline graphic

  • 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 ▶) T min = 0.944, T max = 0.959

  • 41337 measured reflections

  • 11234 independent reflections

  • 5899 reflections with I > 2σ(I)

  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Supplementary Material

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

e-67-0o312-sup1.cif (26.3KB, cif)

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

e-67-0o312-Isup2.hkl (538.2KB, hkl)

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

Acknowledgments

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

supplementary crystallographic information

Comment

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].

Experimental

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

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

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C13H20ClN5 Z = 4
Mr = 281.79 F(000) = 600
Triclinic, P1 Dx = 1.318 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 10.5085 (2) Å Cell parameters from 9620 reflections
b = 11.7016 (3) Å θ = 2.2–27.3°
c = 12.6086 (3) Å µ = 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
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Data collection

Bruker Kappa APEXII diffractometer 11234 independent reflections
Radiation source: fine-focus sealed tube 5899 reflections with I > 2σ(I)
graphite Rint = 0.030
ω and φ scans θmax = 33.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −16→15
Tmin = 0.944, Tmax = 0.959 k = −18→18
41337 measured reflections l = −19→19
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140 H-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 parameters Δρmax = 0.22 e Å−3
0 restraints Δρmin = −0.24 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl1 0.70319 (4) −0.10443 (3) 0.75663 (3) 0.05514 (11)
Cl2 −0.24596 (4) 0.58017 (3) 0.75933 (3) 0.06773 (13)
N1 0.40712 (12) 0.27129 (10) 0.86606 (10) 0.0511 (3)
N2 0.60248 (11) 0.26026 (9) 0.70082 (9) 0.0445 (3)
N3 0.75188 (11) 0.07769 (9) 0.64173 (9) 0.0439 (2)
N4 0.54969 (11) 0.09552 (9) 0.81220 (9) 0.0428 (2)
N5 0.80109 (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)
N10 0.12982 (12) 0.25155 (9) 0.62450 (10) 0.0492 (3)
C1 0.31252 (14) 0.22201 (13) 0.96503 (12) 0.0534 (4)
H1A 0.3136 0.2562 1.0346 0.064*
H1B 0.3429 0.1394 0.9625 0.064*
C2 0.16681 (16) 0.24390 (14) 0.96658 (15) 0.0615 (4)
H2A 0.1040 0.2151 1.0358 0.074*
H2B 0.1638 0.2024 0.9013 0.074*
C3 0.11979 (17) 0.37162 (14) 0.96222 (15) 0.0659 (4)
H3A 0.1112 0.4120 1.0322 0.079*
H3B 0.0293 0.3832 0.9566 0.079*
C4 0.22327 (18) 0.42082 (14) 0.85997 (14) 0.0690 (5)
H4A 0.2216 0.3882 0.7900 0.083*
H4B 0.1962 0.5039 0.8625 0.083*
C5 0.36840 (17) 0.39485 (12) 0.85844 (14) 0.0615 (4)
H5A 0.4330 0.4204 0.7882 0.074*
H5B 0.3737 0.4369 0.9224 0.074*
C6 0.52309 (13) 0.20869 (11) 0.79053 (11) 0.0404 (3)
C7 0.71608 (13) 0.19218 (11) 0.62899 (11) 0.0418 (3)
C8 0.66359 (12) 0.04159 (10) 0.73336 (11) 0.0388 (3)
C9 0.77292 (19) 0.35800 (13) 0.51028 (13) 0.0637 (4)
H9A 0.8475 0.3984 0.5097 0.076*
H9B 0.6871 0.3960 0.5688 0.076*
C10 0.76069 (17) 0.36363 (13) 0.39468 (13) 0.0612 (4)
H10A 0.6788 0.3322 0.3983 0.073*
H10B 0.7499 0.4437 0.3750 0.073*
C11 0.88763 (17) 0.29627 (15) 0.30323 (13) 0.0624 (4)
H11A 0.9677 0.3339 0.2923 0.075*
H11B 0.8740 0.2952 0.2313 0.075*
C12 0.91444 (15) 0.17377 (14) 0.33667 (13) 0.0583 (4)
H12A 0.8394 0.1334 0.3384 0.070*
H12B 1.0001 0.1336 0.2797 0.070*
C13 0.92525 (14) 0.17194 (15) 0.45222 (12) 0.0562 (4)
H13A 0.9362 0.0927 0.4742 0.067*
H13B 1.0063 0.2048 0.4486 0.067*
C14 0.18931 (16) 0.12999 (12) 0.62002 (13) 0.0565 (4)
H14A 0.1827 0.0888 0.5561 0.068*
H14B 0.1371 0.0954 0.6899 0.068*
C15 0.33961 (17) 0.11873 (14) 0.60639 (14) 0.0640 (4)
H15A 0.3450 0.1513 0.6750 0.077*
H15B 0.3794 0.0375 0.5974 0.077*
C16 0.42257 (15) 0.17999 (14) 0.50403 (14) 0.0610 (4)
H16A 0.4271 0.1416 0.4344 0.073*
H16B 0.5166 0.1767 0.5010 0.073*
C17 0.35592 (15) 0.30484 (14) 0.51179 (14) 0.0601 (4)
H17A 0.3621 0.3454 0.5762 0.072*
H17B 0.4060 0.3415 0.4426 0.072*
C18 0.20574 (14) 0.31413 (13) 0.52655 (12) 0.0521 (3)
H18A 0.1638 0.3949 0.5378 0.063*
H18B 0.1999 0.2826 0.4577 0.063*
C19 0.00440 (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 −0.4544 0.2140 1.0314 0.071*
H22B −0.4147 0.3390 1.0227 0.071*
C23 −0.37895 (16) 0.25251 (15) 1.15248 (13) 0.0607 (4)
H23A −0.4711 0.2758 1.2105 0.073*
H23B −0.3196 0.3056 1.1599 0.073*
C24 −0.32291 (16) 0.13175 (15) 1.17191 (13) 0.0605 (4)
H24A −0.3888 0.0805 1.1752 0.073*
H24B −0.3116 0.1314 1.2448 0.073*
C25 −0.18487 (15) 0.08791 (14) 1.07732 (14) 0.0586 (4)
H25A −0.1156 0.1326 1.0808 0.070*
H25B −0.1553 0.0078 1.0881 0.070*
C26 −0.19536 (17) 0.09730 (13) 0.96164 (13) 0.0616 (4)
H26A −0.1041 0.0749 0.9019 0.074*
H26B −0.2558 0.0452 0.9544 0.074*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.0520 (2) 0.04075 (19) 0.0592 (2) 0.00433 (14) −0.01014 (16) 0.00949 (15)
Cl2 0.0742 (3) 0.0482 (2) 0.0646 (3) 0.01757 (18) −0.0179 (2) 0.00811 (18)
N1 0.0514 (6) 0.0375 (6) 0.0469 (6) 0.0045 (5) −0.0031 (5) 0.0045 (5)
N2 0.0512 (6) 0.0386 (6) 0.0376 (6) −0.0052 (5) −0.0105 (5) 0.0023 (5)
N3 0.0423 (6) 0.0431 (6) 0.0395 (6) −0.0031 (5) −0.0092 (5) 0.0041 (5)
N4 0.0420 (6) 0.0381 (6) 0.0409 (6) −0.0006 (4) −0.0095 (5) 0.0057 (5)
N5 0.0596 (7) 0.0488 (7) 0.0466 (7) −0.0069 (6) −0.0025 (6) 0.0104 (5)
N6 0.0514 (7) 0.0514 (7) 0.0510 (7) 0.0000 (5) −0.0017 (6) 0.0114 (6)
N7 0.0456 (6) 0.0464 (6) 0.0432 (6) 0.0032 (5) −0.0140 (5) 0.0030 (5)
N8 0.0491 (6) 0.0381 (6) 0.0439 (6) 0.0004 (5) −0.0125 (5) 0.0053 (5)
N9 0.0442 (6) 0.0380 (6) 0.0401 (6) −0.0026 (5) −0.0098 (5) 0.0031 (5)
N10 0.0464 (6) 0.0375 (6) 0.0482 (7) −0.0009 (5) −0.0023 (5) 0.0069 (5)
C1 0.0510 (8) 0.0489 (8) 0.0439 (8) 0.0047 (6) −0.0042 (6) 0.0076 (6)
C2 0.0512 (8) 0.0541 (9) 0.0659 (10) −0.0005 (7) −0.0100 (7) −0.0025 (8)
C3 0.0541 (9) 0.0586 (10) 0.0753 (11) 0.0103 (7) −0.0205 (8) −0.0064 (8)
C4 0.0862 (12) 0.0459 (9) 0.0638 (10) 0.0182 (8) −0.0262 (9) −0.0009 (7)
C5 0.0666 (10) 0.0371 (8) 0.0593 (9) 0.0024 (7) −0.0034 (8) 0.0018 (7)
C6 0.0438 (6) 0.0370 (6) 0.0369 (6) −0.0024 (5) −0.0128 (5) 0.0016 (5)
C7 0.0450 (7) 0.0417 (7) 0.0376 (7) −0.0086 (5) −0.0139 (6) 0.0035 (5)
C8 0.0391 (6) 0.0366 (6) 0.0395 (7) −0.0016 (5) −0.0150 (5) 0.0024 (5)
C9 0.0852 (11) 0.0450 (8) 0.0488 (9) −0.0179 (8) −0.0090 (8) 0.0100 (7)
C10 0.0726 (10) 0.0467 (8) 0.0640 (10) −0.0146 (7) −0.0237 (8) 0.0136 (7)
C11 0.0685 (10) 0.0742 (11) 0.0474 (9) −0.0218 (8) −0.0213 (8) 0.0113 (8)
C12 0.0466 (8) 0.0683 (10) 0.0529 (9) −0.0049 (7) −0.0122 (7) −0.0012 (7)
C13 0.0401 (7) 0.0713 (10) 0.0491 (8) −0.0091 (7) −0.0076 (6) 0.0127 (7)
C14 0.0594 (9) 0.0359 (7) 0.0556 (9) 0.0022 (6) −0.0043 (7) 0.0030 (6)
C15 0.0658 (10) 0.0557 (9) 0.0587 (9) 0.0145 (7) −0.0188 (8) −0.0019 (7)
C16 0.0459 (8) 0.0655 (10) 0.0610 (10) 0.0016 (7) −0.0120 (7) −0.0065 (8)
C17 0.0532 (8) 0.0596 (10) 0.0573 (9) −0.0124 (7) −0.0080 (7) −0.0017 (7)
C18 0.0517 (8) 0.0460 (8) 0.0479 (8) −0.0044 (6) −0.0079 (6) 0.0086 (6)
C19 0.0429 (6) 0.0342 (6) 0.0394 (7) −0.0029 (5) −0.0141 (5) 0.0003 (5)
C20 0.0500 (7) 0.0381 (7) 0.0429 (7) 0.0027 (6) −0.0198 (6) 0.0007 (5)
C21 0.0440 (7) 0.0445 (7) 0.0391 (7) −0.0056 (6) −0.0148 (6) 0.0030 (6)
C22 0.0405 (7) 0.0726 (10) 0.0549 (9) −0.0043 (7) −0.0082 (6) 0.0140 (8)
C23 0.0446 (8) 0.0743 (11) 0.0539 (9) −0.0044 (7) −0.0098 (7) −0.0004 (8)
C24 0.0536 (8) 0.0775 (11) 0.0532 (9) −0.0152 (8) −0.0215 (7) 0.0146 (8)
C25 0.0494 (8) 0.0528 (9) 0.0723 (10) −0.0111 (7) −0.0206 (8) 0.0158 (7)
C26 0.0676 (10) 0.0442 (8) 0.0569 (9) −0.0082 (7) −0.0057 (8) 0.0099 (7)
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Geometric parameters (Å, °)

Cl1—C8 1.7493 (12) C9—H9A 0.9700
Cl2—C20 1.7454 (12) C9—H9B 0.9700
N1—C6 1.3426 (16) C10—C11 1.509 (2)
N1—C1 1.4523 (18) C10—H10A 0.9700
N1—C5 1.4569 (17) C10—H10B 0.9700
N2—C6 1.3318 (16) C11—C12 1.510 (2)
N2—C7 1.3403 (16) C11—H11A 0.9700
N3—C8 1.2964 (16) C11—H11B 0.9700
N3—C7 1.3637 (16) C12—C13 1.503 (2)
N4—C8 1.3078 (15) C12—H12A 0.9700
N4—C6 1.3615 (16) C12—H12B 0.9700
N5—C7 1.3371 (17) C13—H13A 0.9700
N5—C13 1.4530 (18) C13—H13B 0.9700
N5—C9 1.4565 (18) C14—C15 1.509 (2)
N6—C21 1.3378 (17) C14—H14A 0.9700
N6—C26 1.4559 (18) C14—H14B 0.9700
N6—C22 1.4575 (18) C15—C16 1.507 (2)
N7—C20 1.3037 (17) C15—H15A 0.9700
N7—C21 1.3587 (16) C15—H15B 0.9700
N8—C20 1.3082 (17) C16—C17 1.512 (2)
N8—C19 1.3607 (15) C16—H16A 0.9700
N9—C19 1.3323 (16) C16—H16B 0.9700
N9—C21 1.3386 (16) C17—C18 1.506 (2)
N10—C19 1.3447 (16) C17—H17A 0.9700
N10—C18 1.4571 (17) C17—H17B 0.9700
N10—C14 1.4602 (16) C18—H18A 0.9700
C1—C2 1.508 (2) C18—H18B 0.9700
C1—H1A 0.9700 C22—C23 1.503 (2)
C1—H1B 0.9700 C22—H22A 0.9700
C2—C3 1.512 (2) C22—H22B 0.9700
C2—H2A 0.9700 C23—C24 1.506 (2)
C2—H2B 0.9700 C23—H23A 0.9700
C3—C4 1.517 (2) C23—H23B 0.9700
C3—H3A 0.9700 C24—C25 1.510 (2)
C3—H3B 0.9700 C24—H24A 0.9700
C4—C5 1.504 (2) C24—H24B 0.9700
C4—H4A 0.9700 C25—C26 1.506 (2)
C4—H4B 0.9700 C25—H25A 0.9700
C5—H5A 0.9700 C25—H25B 0.9700
C5—H5B 0.9700 C26—H26A 0.9700
C9—C10 1.511 (2) C26—H26B 0.9700
C6—N1—C1 122.56 (11) C13—C12—H12B 109.4
C6—N1—C5 123.04 (11) C11—C12—H12B 109.4
C1—N1—C5 114.37 (11) H12A—C12—H12B 108.0
C6—N2—C7 115.16 (11) N5—C13—C12 110.02 (12)
C8—N3—C7 112.00 (11) N5—C13—H13A 109.7
C8—N4—C6 111.91 (11) C12—C13—H13A 109.7
C7—N5—C13 123.28 (12) N5—C13—H13B 109.7
C7—N5—C9 122.63 (12) C12—C13—H13B 109.7
C13—N5—C9 114.01 (12) H13A—C13—H13B 108.2
C21—N6—C26 122.78 (12) N10—C14—C15 110.52 (13)
C21—N6—C22 123.04 (12) N10—C14—H14A 109.5
C26—N6—C22 114.18 (12) C15—C14—H14A 109.5
C20—N7—C21 111.92 (11) N10—C14—H14B 109.5
C20—N8—C19 111.78 (11) C15—C14—H14B 109.5
C19—N9—C21 115.25 (11) H14A—C14—H14B 108.1
C19—N10—C18 122.92 (11) C16—C15—C14 111.44 (13)
C19—N10—C14 122.06 (11) C16—C15—H15A 109.3
C18—N10—C14 114.21 (11) C14—C15—H15A 109.3
N1—C1—C2 110.51 (12) C16—C15—H15B 109.3
N1—C1—H1A 109.5 C14—C15—H15B 109.3
C2—C1—H1A 109.5 H15A—C15—H15B 108.0
N1—C1—H1B 109.5 C15—C16—C17 110.23 (12)
C2—C1—H1B 109.5 C15—C16—H16A 109.6
H1A—C1—H1B 108.1 C17—C16—H16A 109.6
C1—C2—C3 110.93 (13) C15—C16—H16B 109.6
C1—C2—H2A 109.5 C17—C16—H16B 109.6
C3—C2—H2A 109.5 H16A—C16—H16B 108.1
C1—C2—H2B 109.5 C18—C17—C16 111.37 (13)
C3—C2—H2B 109.5 C18—C17—H17A 109.4
H2A—C2—H2B 108.0 C16—C17—H17A 109.4
C2—C3—C4 110.40 (12) C18—C17—H17B 109.4
C2—C3—H3A 109.6 C16—C17—H17B 109.4
C4—C3—H3A 109.6 H17A—C17—H17B 108.0
C2—C3—H3B 109.6 N10—C18—C17 110.78 (12)
C4—C3—H3B 109.6 N10—C18—H18A 109.5
H3A—C3—H3B 108.1 C17—C18—H18A 109.5
C5—C4—C3 111.71 (13) N10—C18—H18B 109.5
C5—C4—H4A 109.3 C17—C18—H18B 109.5
C3—C4—H4A 109.3 H18A—C18—H18B 108.1
C5—C4—H4B 109.3 N9—C19—N10 117.95 (11)
C3—C4—H4B 109.3 N9—C19—N8 125.01 (11)
H4A—C4—H4B 107.9 N10—C19—N8 117.03 (11)
N1—C5—C4 110.60 (13) N7—C20—N8 131.13 (12)
N1—C5—H5A 109.5 N7—C20—Cl2 114.49 (10)
C4—C5—H5A 109.5 N8—C20—Cl2 114.38 (10)
N1—C5—H5B 109.5 N6—C21—N9 117.93 (12)
C4—C5—H5B 109.5 N6—C21—N7 117.19 (12)
H5A—C5—H5B 108.1 N9—C21—N7 124.89 (12)
N2—C6—N1 118.59 (11) N6—C22—C23 110.09 (12)
N2—C6—N4 124.96 (11) N6—C22—H22A 109.6
N1—C6—N4 116.45 (11) C23—C22—H22A 109.6
N5—C7—N2 118.54 (12) N6—C22—H22B 109.6
N5—C7—N3 116.69 (12) C23—C22—H22B 109.6
N2—C7—N3 124.76 (11) H22A—C22—H22B 108.2
N3—C8—N4 131.21 (12) C22—C23—C24 111.25 (13)
N3—C8—Cl1 114.80 (9) C22—C23—H23A 109.4
N4—C8—Cl1 113.99 (9) C24—C23—H23A 109.4
N5—C9—C10 110.38 (12) C22—C23—H23B 109.4
N5—C9—H9A 109.6 C24—C23—H23B 109.4
C10—C9—H9A 109.6 H23A—C23—H23B 108.0
N5—C9—H9B 109.6 C23—C24—C25 111.13 (13)
C10—C9—H9B 109.6 C23—C24—H24A 109.4
H9A—C9—H9B 108.1 C25—C24—H24A 109.4
C11—C10—C9 110.94 (14) C23—C24—H24B 109.4
C11—C10—H10A 109.5 C25—C24—H24B 109.4
C9—C10—H10A 109.5 H24A—C24—H24B 108.0
C11—C10—H10B 109.5 C26—C25—C24 110.94 (12)
C9—C10—H10B 109.5 C26—C25—H25A 109.5
H10A—C10—H10B 108.0 C24—C25—H25A 109.5
C10—C11—C12 110.62 (13) C26—C25—H25B 109.5
C10—C11—H11A 109.5 C24—C25—H25B 109.5
C12—C11—H11A 109.5 H25A—C25—H25B 108.0
C10—C11—H11B 109.5 N6—C26—C25 110.16 (13)
C12—C11—H11B 109.5 N6—C26—H26A 109.6
H11A—C11—H11B 108.1 C25—C26—H26A 109.6
C13—C12—C11 111.11 (13) N6—C26—H26B 109.6
C13—C12—H12A 109.4 C25—C26—H26B 109.6
C11—C12—H12A 109.4 H26A—C26—H26B 108.1
C6—N1—C1—C2 −125.43 (14) C19—N10—C14—C15 −134.48 (14)
C5—N1—C1—C2 56.89 (17) C18—N10—C14—C15 55.57 (17)
N1—C1—C2—C3 −55.30 (17) N10—C14—C15—C16 −54.49 (17)
C1—C2—C3—C4 54.33 (18) C14—C15—C16—C17 54.67 (18)
C2—C3—C4—C5 −53.65 (19) C15—C16—C17—C18 −54.55 (18)
C6—N1—C5—C4 126.52 (15) C19—N10—C18—C17 134.52 (14)
C1—N1—C5—C4 −55.82 (17) C14—N10—C18—C17 −55.63 (17)
C3—C4—C5—N1 53.34 (18) C16—C17—C18—N10 54.34 (17)
C7—N2—C6—N1 −179.74 (11) C21—N9—C19—N10 178.84 (11)
C7—N2—C6—N4 −0.14 (19) C21—N9—C19—N8 −0.91 (19)
C1—N1—C6—N2 178.59 (12) C18—N10—C19—N9 176.73 (12)
C5—N1—C6—N2 −3.9 (2) C14—N10—C19—N9 7.66 (19)
C1—N1—C6—N4 −1.0 (2) C18—N10—C19—N8 −3.49 (19)
C5—N1—C6—N4 176.42 (12) C14—N10—C19—N8 −172.56 (12)
C8—N4—C6—N2 −0.39 (18) C20—N8—C19—N9 0.31 (18)
C8—N4—C6—N1 179.22 (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—Cl2 177.15 (9)
C13—N5—C7—N3 0.9 (2) C19—N8—C20—N7 1.2 (2)
C9—N5—C7—N3 177.51 (13) C19—N8—C20—Cl2 −177.71 (9)
C6—N2—C7—N5 −179.76 (12) C26—N6—C21—N9 1.0 (2)
C6—N2—C7—N3 0.87 (19) C22—N6—C21—N9 −179.42 (13)
C8—N3—C7—N5 179.68 (11) C26—N6—C21—N7 −179.10 (13)
C8—N3—C7—N2 −0.93 (18) C22—N6—C21—N7 0.5 (2)
C7—N3—C8—N4 0.3 (2) C19—N9—C21—N6 −179.88 (12)
C7—N3—C8—Cl1 −179.40 (9) C19—N9—C21—N7 0.25 (19)
C6—N4—C8—N3 0.3 (2) C20—N7—C21—N6 −178.97 (12)
C6—N4—C8—Cl1 −179.99 (8) C20—N7—C21—N9 0.90 (19)
C7—N5—C9—C10 −119.80 (16) C21—N6—C22—C23 −122.32 (16)
C13—N5—C9—C10 57.09 (18) C26—N6—C22—C23 57.27 (18)
N5—C9—C10—C11 −54.29 (18) N6—C22—C23—C24 −54.38 (18)
C9—C10—C11—C12 54.06 (17) C22—C23—C24—C25 53.98 (17)
C10—C11—C12—C13 −54.84 (17) C23—C24—C25—C26 −53.93 (18)
C7—N5—C13—C12 119.29 (15) C21—N6—C26—C25 122.17 (15)
C9—N5—C13—C12 −57.58 (18) C22—N6—C26—C25 −57.43 (18)
C11—C12—C13—N5 55.47 (17) C24—C25—C26—N6 54.50 (17)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
C9—H9B···N2 0.97 2.32 2.7637 (18) 107
C13—H13A···N3 0.97 2.30 2.7472 (17) 107
C14—H14B···N9 0.97 2.31 2.7497 (18) 106
C18—H18A···N8 0.97 2.32 2.7560 (18) 106
C22—H22B···N7 0.97 2.30 2.7532 (19) 107
C26—H26A···N9 0.97 2.31 2.7534 (18) 107
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2259).

References

  1. 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.
  2. Azev, Y. A., Dulcks, T. & Gabel, D. (2003). Tetrahedron Lett. 44, 8689–8691.
  3. Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
  5. Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  8. Steffensen, M. B. & Simanek, E. E. (2003). Org. Lett. 5, 2359–2361. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-0o312-sup1.cif (26.3KB, cif)

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

e-67-0o312-Isup2.hkl (538.2KB, hkl)

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

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

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