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

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ISSN: 2056-9890

2,4-Bis(morpholin-4-yl)-6-phen­­oxy-1,3,5-triazine

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: chakkaravarthi_2005@yahoo.com

(Received 7 August 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, C17H21N5O3, the dihedral angle between the triazine and the phenyl ring is 80.31 (11)°. One of the morpholine rings is disordered over two orientations with site occupancies of 0.762 (10) and 0.238 (10). Both morpholine rings in the mol­ecule adopt chair conformations.

Related literature

For triazine derivatives, 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 related structures, see: Zeng et al. (2005[Zeng, T., Dong, C.-M., Shu, X.-G., Li, J.-S. & Huang, P.-M. (2005). Acta Cryst. E61, o2211-o2212.]); Jian et al. (2007[Jian, F.-F., Wei, Y.-X., Huang, L.-H. & Ren, X.-Y. (2007). Acta Cryst. E63, o4937.]); Vennila et al. (2011[Vennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Chakkaravarthi, G. & Manivannan, V. (2011). Acta Cryst. E67, o312.]). 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
  • C17H21N5O3

  • Mr = 343.39

  • Orthorhombic, P 21 21 21

  • a = 8.6788 (5) Å

  • b = 11.2461 (5) Å

  • c = 17.9778 (10) Å

  • V = 1754.68 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 295 K

  • 0.30 × 0.24 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.982

  • 18679 measured reflections

  • 2028 independent reflections

  • 1613 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.05

  • 2028 reflections

  • 272 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2. 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


Comment top

1,3,5-Triazine derivatives are of importance as starting materials for drugs and light stabilizers (Azev et al., 2003; Steffensen & Simanek, 2003). The bond lengths and angles are comparable with similar reported structures (Zeng et al., 2005; Jian et al., 2007; Vennila et al., 2011). The dihedral angle between the triazine (C7/N1/C8/N2/C9/N3) ring and the phenyl ring (C1—C6) is 80.31 (11)°.

In the molecule, one of the morpholine rings is disordered over two orientations with site occupancies of 0.762 (10) and 0.238 (10). The morpholine ring N4/C10/C11/O2/C12/C13 and the disordered morpholine ring [with major site occupancy orientation (N5/C14/C15/O3/C16/C17) and minor site occupancy orientation (N5A/C14A/C15A/O3A/C16A/C17A)] adopt chair conformations (Cremer & Pople, 1975): Q = 0.547 (3) Å, θ = 175.9 (3)°, Φ = 174 (5)° for the ring N4/C10/C11/O2/C12/C13; Q = 0.551 (6) Å, θ = 3.1 (7)°, Φ = 246 (11)° for the disordered ring (N5/C14/C15/O3/C16/C17) and Q = 0.68 (2) Å, θ = 167.6 (15)°, Φ = 169 (9)° for the disordered ring (N5A/C14A/C15A/O3A/C16A/C17A).

Related literature top

For related literature on triazine derivatives, see: Azev et al. (2003); Steffensen & Simanek (2003). For related structures, see: Zeng et al. (2005); Jian et al. (2007); Vennila et al. (2011). For puckering and asymmetry parameters, see: Cremer & Pople (1975).

Experimental top

A solution of cyanuric chloride (1.85 g, 10 mmol) in 6 ml acetone was added with stirring to a cold solution (0–5°C) of sodium bicarbonate (0.85 g, 10 mmol) in 10 ml of distilled water in a three necked flask equipped with a mechanical stirrer. This resulted in the formation of a slurry of cyanuric chloride. A solution of phenol (1 ml) in 5 ml acetone was added to the cold slurry of cyanuric chloride. After some time, the reaction mixture was neutralized by a saturated solution of sodium bicarbonate. The mixture was stirred for 2 h at 0–5°C. The crude product obtained was filtered and recrystallized from ethanol. To this product (1.75 g, 5 mmol) in acetone (5 ml), a mixture of NaOH (0.08 g, 20 mmol) and morpholine (1 ml) in 8 ml double distilled water was added slowly at room temperature with constant stirring. Stirring was continued for 4 h initially for 2 h at room temperature and another 2 h at 80°C. The crude product was filtered and recystallized from ethanol to yield colourless diffraction quality crystals.

Refinement top

Due to the absence of anomalous scatterers, 1495 Friedel pairs have been merged. Site occupancy factors of disordered atoms in the morpholine ring (A) were refined as 0.762 (10) for major orientation (N5/C14/C15/O3/C16/C17) and 0.238 (10) for minor orientation (N5A/C14A/C15A/O3A/C16A/C17A). All H atoms were positioned geometrically with C—H = 0.93–0.97 Å and allowed to ride on their parent atoms, 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.
2,4-Bis(morpholin-4-yl)-6-phenoxy-1,3,5-triazine top
Crystal data top
C17H21N5O3F(000) = 728
Mr = 343.39Dx = 1.300 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5915 reflections
a = 8.6788 (5) Åθ = 2.3–26.2°
b = 11.2461 (5) ŵ = 0.09 mm1
c = 17.9778 (10) ÅT = 295 K
V = 1754.68 (16) Å3Block, colourless
Z = 40.30 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2028 independent reflections
Radiation source: fine-focus sealed tube1613 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and ϕ scansθmax = 26.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.973, Tmax = 0.982k = 1214
18679 measured reflectionsl = 2222
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.2172P]
where P = (Fo2 + 2Fc2)/3
2028 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C17H21N5O3V = 1754.68 (16) Å3
Mr = 343.39Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6788 (5) ŵ = 0.09 mm1
b = 11.2461 (5) ÅT = 295 K
c = 17.9778 (10) Å0.30 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2028 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1613 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.982Rint = 0.031
18679 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.05Δρmax = 0.16 e Å3
2028 reflectionsΔρmin = 0.14 e Å3
272 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.2358 (3)0.06378 (14)0.28176 (9)0.0714 (6)
O20.2262 (3)0.28572 (15)0.65046 (9)0.0675 (6)
N10.2683 (3)0.08734 (16)0.35905 (11)0.0546 (6)
N20.3107 (3)0.05145 (16)0.48804 (11)0.0585 (6)
N30.2685 (3)0.11092 (15)0.40465 (9)0.0504 (5)
N40.3066 (4)0.14047 (16)0.52974 (11)0.0696 (8)
N50.3017 (4)0.24105 (17)0.44123 (12)0.0736 (8)
C10.2359 (4)0.1847 (2)0.26391 (12)0.0534 (7)
C20.3713 (4)0.2430 (3)0.25415 (18)0.0691 (8)
H20.46470.20520.26340.083*
C30.3672 (5)0.3596 (3)0.23017 (18)0.0786 (10)
H30.45910.40060.22290.094*
C40.2318 (5)0.4150 (3)0.21713 (15)0.0771 (10)
H40.23070.49390.20170.092*
C50.0974 (5)0.3553 (3)0.22666 (19)0.0813 (10)
H50.00430.39340.21710.098*
C60.0975 (4)0.2388 (3)0.25034 (18)0.0687 (8)
H60.00550.19780.25700.082*
C70.2598 (3)0.02907 (19)0.35318 (12)0.0487 (6)
C80.2933 (3)0.1225 (2)0.42922 (13)0.0543 (6)
C90.2951 (3)0.06457 (19)0.47306 (12)0.0513 (6)
C100.3399 (5)0.1037 (2)0.60578 (14)0.0746 (10)
H10A0.44390.12710.61910.089*
H10B0.33250.01780.60980.089*
C110.2281 (5)0.1604 (2)0.65710 (14)0.0734 (9)
H11A0.12580.12980.64680.088*
H11B0.25420.13920.70790.088*
C120.1844 (4)0.3172 (2)0.57681 (16)0.0715 (9)
H12A0.18070.40310.57260.086*
H12B0.08220.28660.56620.086*
C130.2946 (5)0.2695 (2)0.52140 (14)0.0703 (9)
H13A0.25960.28880.47160.084*
H13B0.39500.30570.52870.084*
C140.2687 (13)0.3314 (8)0.3851 (5)0.078 (3)0.701 (10)
H14A0.16420.36030.39140.093*0.701 (10)
H14B0.27740.29680.33590.093*0.701 (10)
C150.3741 (12)0.4272 (4)0.3923 (3)0.099 (3)0.701 (10)
H15A0.34640.48840.35670.119*0.701 (10)
H15B0.47640.39910.37950.119*0.701 (10)
O30.3791 (8)0.4783 (4)0.4637 (3)0.0897 (16)0.701 (10)
C160.4171 (8)0.3914 (4)0.5164 (3)0.0720 (15)0.701 (10)
H16A0.51820.35920.50520.086*0.701 (10)
H16B0.42140.42740.56540.086*0.701 (10)
C170.3037 (12)0.2952 (7)0.5166 (4)0.071 (2)0.701 (10)
H17A0.33140.23580.55340.086*0.701 (10)
H17B0.20260.32610.52880.086*0.701 (10)
C14A0.305 (5)0.314 (2)0.3745 (16)0.158 (16)0.299 (10)
H14C0.40990.33560.36110.189*0.299 (10)
H14D0.25680.27400.33280.189*0.299 (10)
C15A0.214 (3)0.4207 (11)0.3988 (7)0.104 (7)0.299 (10)
H15C0.10680.39770.40420.124*0.299 (10)
H15D0.21920.48070.36010.124*0.299 (10)
O3A0.265 (3)0.4716 (10)0.4665 (7)0.123 (7)0.299 (10)
C16A0.273 (5)0.3884 (12)0.5234 (7)0.147 (13)0.299 (10)
H16C0.31270.42830.56720.177*0.299 (10)
H16D0.16880.36320.53480.177*0.299 (10)
C17A0.368 (4)0.279 (2)0.5111 (16)0.128 (13)0.299 (10)
H17C0.35260.22090.55020.154*0.299 (10)
H17D0.47650.29750.50660.154*0.299 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1290 (18)0.0440 (8)0.0412 (9)0.0023 (12)0.0188 (11)0.0017 (7)
O20.0994 (15)0.0550 (10)0.0481 (9)0.0018 (11)0.0051 (10)0.0090 (8)
N10.0788 (16)0.0392 (9)0.0457 (10)0.0056 (10)0.0109 (11)0.0036 (8)
N20.0933 (18)0.0368 (9)0.0456 (11)0.0045 (11)0.0062 (12)0.0008 (8)
N30.0768 (15)0.0358 (8)0.0387 (9)0.0018 (11)0.0034 (10)0.0004 (7)
N40.132 (2)0.0381 (10)0.0388 (11)0.0057 (13)0.0024 (13)0.0010 (8)
N50.132 (2)0.0355 (10)0.0535 (12)0.0106 (13)0.0188 (15)0.0033 (9)
C10.082 (2)0.0453 (11)0.0325 (10)0.0048 (14)0.0042 (12)0.0001 (9)
C20.069 (2)0.073 (2)0.0656 (18)0.0070 (16)0.0059 (15)0.0014 (16)
C30.091 (2)0.077 (2)0.068 (2)0.020 (2)0.0049 (17)0.0118 (17)
C40.124 (3)0.0561 (15)0.0506 (14)0.003 (2)0.0017 (19)0.0153 (12)
C50.087 (2)0.074 (2)0.083 (2)0.0228 (19)0.0038 (17)0.0235 (18)
C60.0678 (19)0.073 (2)0.0654 (18)0.0020 (16)0.0034 (14)0.0142 (16)
C70.0647 (16)0.0413 (11)0.0402 (11)0.0033 (12)0.0062 (11)0.0020 (9)
C80.0754 (18)0.0386 (11)0.0490 (13)0.0083 (13)0.0081 (13)0.0040 (10)
C90.0766 (17)0.0369 (10)0.0403 (11)0.0040 (12)0.0015 (12)0.0008 (9)
C100.130 (3)0.0500 (13)0.0435 (13)0.0165 (18)0.0122 (17)0.0005 (11)
C110.117 (3)0.0575 (15)0.0458 (13)0.0086 (18)0.0039 (16)0.0026 (11)
C120.102 (2)0.0504 (13)0.0623 (16)0.0093 (16)0.0080 (16)0.0036 (13)
C130.125 (3)0.0349 (11)0.0510 (14)0.0004 (15)0.0050 (17)0.0031 (10)
C140.148 (6)0.032 (3)0.054 (3)0.004 (3)0.041 (4)0.001 (2)
C150.186 (8)0.050 (3)0.062 (3)0.038 (4)0.004 (4)0.005 (2)
O30.159 (5)0.0407 (18)0.070 (2)0.024 (3)0.001 (3)0.0062 (15)
C160.102 (4)0.048 (2)0.066 (3)0.003 (3)0.011 (3)0.011 (2)
C170.127 (7)0.036 (3)0.051 (3)0.001 (4)0.011 (4)0.000 (2)
C14A0.33 (4)0.042 (9)0.106 (15)0.014 (15)0.073 (19)0.017 (9)
C15A0.18 (2)0.054 (7)0.077 (8)0.033 (10)0.003 (10)0.002 (6)
O3A0.26 (2)0.037 (4)0.076 (6)0.022 (9)0.014 (12)0.005 (4)
C16A0.34 (4)0.059 (8)0.046 (6)0.057 (16)0.001 (13)0.005 (5)
C17A0.19 (3)0.055 (9)0.135 (18)0.042 (13)0.100 (19)0.032 (9)
Geometric parameters (Å, º) top
O1—C71.358 (3)C11—H11A0.9700
O1—C11.397 (3)C11—H11B0.9700
O2—C111.415 (3)C12—C131.481 (4)
O2—C121.418 (3)C12—H12A0.9700
N1—C71.315 (3)C12—H12B0.9700
N1—C81.340 (3)C13—H13A0.9700
N2—C81.334 (3)C13—H13B0.9700
N2—C91.339 (3)C14—C151.420 (11)
N3—C71.307 (3)C14—H14A0.9700
N3—C91.356 (3)C14—H14B0.9700
N4—C91.333 (3)C15—O31.407 (7)
N4—C101.457 (3)C15—H15A0.9700
N4—C131.463 (3)C15—H15B0.9700
N5—C81.352 (3)O3—C161.401 (7)
N5—C17A1.45 (3)C16—C171.463 (11)
N5—C14A1.45 (3)C16—H16A0.9700
N5—C141.460 (9)C16—H16B0.9700
N5—C171.485 (9)C17—H17A0.9700
C1—C21.357 (4)C17—H17B0.9700
C1—C61.368 (4)C14A—C15A1.50 (3)
C2—C31.381 (4)C14A—H14C0.9700
C2—H20.9300C14A—H14D0.9700
C3—C41.351 (5)C15A—O3A1.415 (19)
C3—H30.9300C15A—H15C0.9700
C4—C51.357 (5)C15A—H15D0.9700
C4—H40.9300O3A—C16A1.389 (17)
C5—C61.378 (4)C16A—C17A1.49 (3)
C5—H50.9300C16A—H16C0.9700
C6—H60.9300C16A—H16D0.9700
C10—C111.483 (4)C17A—H17C0.9700
C10—H10A0.9700C17A—H17D0.9700
C10—H10B0.9700
C7—O1—C1119.79 (17)C13—C12—H12B109.2
C11—O2—C12109.3 (2)H12A—C12—H12B107.9
C7—N1—C8112.24 (19)N4—C13—C12109.6 (2)
C8—N2—C9114.4 (2)N4—C13—H13A109.7
C7—N3—C9112.42 (18)C12—C13—H13A109.7
C9—N4—C10123.4 (2)N4—C13—H13B109.7
C9—N4—C13123.5 (2)C12—C13—H13B109.7
C10—N4—C13113.1 (2)H13A—C13—H13B108.2
C8—N5—C17A116.9 (10)C15—C14—N5109.9 (5)
C8—N5—C14A115.2 (12)C15—C14—H14A109.7
C17A—N5—C14A122.7 (18)N5—C14—H14A109.7
C8—N5—C14124.4 (4)C15—C14—H14B109.7
C17A—N5—C14118.1 (11)N5—C14—H14B109.7
C8—N5—C17123.4 (3)H14A—C14—H14B108.2
C14A—N5—C17121.4 (12)O3—C15—C14114.3 (6)
C14—N5—C17110.3 (5)O3—C15—H15A108.7
C2—C1—C6121.5 (2)C14—C15—H15A108.7
C2—C1—O1120.0 (3)O3—C15—H15B108.7
C6—C1—O1118.3 (3)C14—C15—H15B108.7
C1—C2—C3118.5 (3)H15A—C15—H15B107.6
C1—C2—H2120.7C16—O3—C15109.9 (4)
C3—C2—H2120.7O3—C16—C17111.0 (5)
C4—C3—C2121.0 (3)O3—C16—H16A109.4
C4—C3—H3119.5C17—C16—H16A109.4
C2—C3—H3119.5O3—C16—H16B109.4
C3—C4—C5119.8 (3)C17—C16—H16B109.4
C3—C4—H4120.1H16A—C16—H16B108.0
C5—C4—H4120.1C16—C17—N5108.0 (6)
C4—C5—C6120.6 (3)C16—C17—H17A110.1
C4—C5—H5119.7N5—C17—H17A110.1
C6—C5—H5119.7C16—C17—H17B110.1
C1—C6—C5118.6 (3)N5—C17—H17B110.1
C1—C6—H6120.7H17A—C17—H17B108.4
C5—C6—H6120.7N5—C14A—C15A102 (2)
N3—C7—N1129.8 (2)N5—C14A—H14C111.5
N3—C7—O1118.40 (19)C15A—C14A—H14C111.5
N1—C7—O1111.74 (18)N5—C14A—H14D111.5
N2—C8—N1126.0 (2)C15A—C14A—H14D111.5
N2—C8—N5117.2 (2)H14C—C14A—H14D109.3
N1—C8—N5116.8 (2)O3A—C15A—C14A114.1 (18)
N4—C9—N2117.6 (2)O3A—C15A—H15C108.7
N4—C9—N3117.40 (19)C14A—C15A—H15C108.7
N2—C9—N3125.0 (2)O3A—C15A—H15D108.7
N4—C10—C11109.4 (3)C14A—C15A—H15D108.7
N4—C10—H10A109.8H15C—C15A—H15D107.6
C11—C10—H10A109.8C16A—O3A—C15A112.2 (12)
N4—C10—H10B109.8O3A—C16A—C17A118.2 (19)
C11—C10—H10B109.8O3A—C16A—H16C107.7
H10A—C10—H10B108.2C17A—C16A—H16C107.7
O2—C11—C10112.6 (3)O3A—C16A—H16D107.7
O2—C11—H11A109.1C17A—C16A—H16D107.7
C10—C11—H11A109.1H16C—C16A—H16D107.1
O2—C11—H11B109.1N5—C17A—C16A98.9 (19)
C10—C11—H11B109.1N5—C17A—H17C112.0
H11A—C11—H11B107.8C16A—C17A—H17C112.0
O2—C12—C13111.9 (3)N5—C17A—H17D112.0
O2—C12—H12A109.2C16A—C17A—H17D112.0
C13—C12—H12A109.2H17C—C17A—H17D109.7
O2—C12—H12B109.2
C7—O1—C1—C280.8 (3)C7—N3—C9—N4179.8 (3)
C7—O1—C1—C6104.8 (3)C7—N3—C9—N20.2 (4)
C6—C1—C2—C30.2 (4)C9—N4—C10—C11131.2 (3)
O1—C1—C2—C3174.4 (2)C13—N4—C10—C1151.6 (4)
C1—C2—C3—C40.4 (5)C12—O2—C11—C1060.2 (4)
C2—C3—C4—C50.9 (5)N4—C10—C11—O255.6 (4)
C3—C4—C5—C60.7 (5)C11—O2—C12—C1360.3 (4)
C2—C1—C6—C50.4 (4)C9—N4—C13—C12130.6 (3)
O1—C1—C6—C5174.7 (3)C10—N4—C13—C1252.2 (4)
C4—C5—C6—C10.1 (5)O2—C12—C13—N456.2 (4)
C9—N3—C7—N12.3 (4)C8—N5—C14—C15141.3 (6)
C9—N3—C7—O1179.0 (3)C17A—N5—C14—C1530 (2)
C8—N1—C7—N31.8 (5)C14A—N5—C14—C1581 (6)
C8—N1—C7—O1179.4 (2)C17—N5—C14—C1553.9 (11)
C1—O1—C7—N36.1 (4)N5—C14—C15—O354.9 (11)
C1—O1—C7—N1174.9 (3)C14—C15—O3—C1657.8 (9)
C9—N2—C8—N12.6 (4)C15—O3—C16—C1759.7 (8)
C9—N2—C8—N5177.5 (3)O3—C16—C17—N559.9 (8)
C7—N1—C8—N20.9 (4)C8—N5—C17—C16138.5 (5)
C7—N1—C8—N5179.1 (3)C17A—N5—C17—C1658 (3)
C17A—N5—C8—N215.7 (17)C14A—N5—C17—C1643 (2)
C14A—N5—C8—N2171.2 (19)C14—N5—C17—C1656.5 (9)
C14—N5—C8—N2173.0 (7)C8—N5—C14A—C15A144.3 (15)
C17—N5—C8—N210.1 (7)C17A—N5—C14A—C15A62 (3)
C17A—N5—C8—N1164.2 (16)C14—N5—C14A—C15A17 (4)
C14A—N5—C8—N18.8 (19)C17—N5—C14A—C15A34 (3)
C14—N5—C8—N17.1 (7)N5—C14A—C15A—O3A52 (3)
C17—N5—C8—N1169.9 (5)C14A—C15A—O3A—C16A53 (3)
C10—N4—C9—N22.0 (5)C15A—O3A—C16A—C17A55 (3)
C13—N4—C9—N2178.9 (3)C8—N5—C17A—C16A146.4 (17)
C10—N4—C9—N3177.9 (3)C14A—N5—C17A—C16A60 (4)
C13—N4—C9—N31.0 (5)C14—N5—C17A—C16A42 (3)
C8—N2—C9—N4178.1 (3)C17—N5—C17A—C16A34 (2)
C8—N2—C9—N31.9 (4)O3A—C16A—C17A—N552 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N20.972.332.755 (3)106
C13—H13A···N30.972.342.764 (3)106
C14—H14B···N10.972.392.784 (9)104
C17—H17A···N20.972.392.789 (9)104

Experimental details

Crystal data
Chemical formulaC17H21N5O3
Mr343.39
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)8.6788 (5), 11.2461 (5), 17.9778 (10)
V3)1754.68 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.24 × 0.20
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.973, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
18679, 2028, 1613
Rint0.031
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.05
No. of reflections2028
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.14

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
C10—H10B···N20.972.332.755 (3)106
C13—H13A···N30.972.342.764 (3)106
C14—H14B···N10.972.392.784 (9)104
C17—H17A···N20.972.392.789 (9)104
 

Acknowledgements

The authors acknowledge SAIF, IIT, Madras for data collection.

References

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. 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 citationJian, F.-F., Wei, Y.-X., Huang, L.-H. & Ren, X.-Y. (2007). Acta Cryst. E63, o4937.  Web of Science CSD CrossRef IUCr Journals 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
First citationVennila, J. P., Thiruvadigal, D. J., Kavitha, H. P., Chakkaravarthi, G. & Manivannan, V. (2011). Acta Cryst. E67, o312.  CrossRef IUCr Journals Google Scholar
First citationZeng, T., Dong, C.-M., Shu, X.-G., Li, J.-S. & Huang, P.-M. (2005). Acta Cryst. E61, o2211–o2212.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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