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

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

doi:10.1107/S1600536811034088

organic compounds

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Volume 67| Part 9| September 2011| Page o2451

doi:10.1107/S1600536811034088

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

Jasmine P. Vennila,^a D. John Thiruvadigal,^b Helen P. Kavitha,^c G. Chakkaravarthi ^d ^* and V. Manivannan ^e

^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 ); 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

Crystal data

C₁₇H₂₁N₅O₃
M_r = 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 ) T_min = 0.973, T_max = 0.982
18679 measured reflections
2028 independent reflections
1613 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.05
2028 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034088/bt5604sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034088/bt5604Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034088/bt5604Isup3.cml

checkCIF report

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.

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

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

C₁₇H₂₁N₅O₃	F(000) = 728
M_r = 343.39	D_x = 1.300 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5915 reflections
a = 8.6788 (5) Å	θ = 2.3–26.2°
b = 11.2461 (5) Å	µ = 0.09 mm⁻¹
c = 17.9778 (10) Å	T = 295 K
V = 1754.68 (16) Å³	Block, colourless
Z = 4	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	2028 independent reflections
Radiation source: fine-focus sealed tube	1613 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 26.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.973, T_max = 0.982	k = −12→14
18679 measured reflections	l = −22→22

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0642P)² + 0.2172P] where P = (F_o² + 2F_c²)/3
2028 reflections	(Δ/σ)_max < 0.001
272 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₂₁N₅O₃	V = 1754.68 (16) Å³
M_r = 343.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.6788 (5) Å	µ = 0.09 mm⁻¹
b = 11.2461 (5) Å	T = 295 K
c = 17.9778 (10) Å	0.30 × 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)
T_min = 0.973, T_max = 0.982	R_int = 0.031
18679 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
2028 reflections	Δρ_min = −0.14 e Å⁻³
272 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.2358 (3)	0.06378 (14)	0.28176 (9)	0.0714 (6)
O2	0.2262 (3)	0.28572 (15)	0.65046 (9)	0.0675 (6)
N1	0.2683 (3)	−0.08734 (16)	0.35905 (11)	0.0546 (6)
N2	0.3107 (3)	−0.05145 (16)	0.48804 (11)	0.0585 (6)
N3	0.2685 (3)	0.11092 (15)	0.40465 (9)	0.0504 (5)
N4	0.3066 (4)	0.14047 (16)	0.52974 (11)	0.0696 (8)
N5	0.3017 (4)	−0.24105 (17)	0.44123 (12)	0.0736 (8)
C1	0.2359 (4)	0.1847 (2)	0.26391 (12)	0.0534 (7)
C2	0.3713 (4)	0.2430 (3)	0.25415 (18)	0.0691 (8)
H2	0.4647	0.2052	0.2634	0.083*
C3	0.3672 (5)	0.3596 (3)	0.23017 (18)	0.0786 (10)
H3	0.4591	0.4006	0.2229	0.094*
C4	0.2318 (5)	0.4150 (3)	0.21713 (15)	0.0771 (10)
H4	0.2307	0.4939	0.2017	0.092*
C5	0.0974 (5)	0.3553 (3)	0.22666 (19)	0.0813 (10)
H5	0.0043	0.3934	0.2171	0.098*
C6	0.0975 (4)	0.2388 (3)	0.25034 (18)	0.0687 (8)
H6	0.0055	0.1978	0.2570	0.082*
C7	0.2598 (3)	0.02907 (19)	0.35318 (12)	0.0487 (6)
C8	0.2933 (3)	−0.1225 (2)	0.42922 (13)	0.0543 (6)
C9	0.2951 (3)	0.06457 (19)	0.47306 (12)	0.0513 (6)
C10	0.3399 (5)	0.1037 (2)	0.60578 (14)	0.0746 (10)
H10A	0.4439	0.1271	0.6191	0.089*
H10B	0.3325	0.0178	0.6098	0.089*
C11	0.2281 (5)	0.1604 (2)	0.65710 (14)	0.0734 (9)
H11A	0.1258	0.1298	0.6468	0.088*
H11B	0.2542	0.1392	0.7079	0.088*
C12	0.1844 (4)	0.3172 (2)	0.57681 (16)	0.0715 (9)
H12A	0.1807	0.4031	0.5726	0.086*
H12B	0.0822	0.2866	0.5662	0.086*
C13	0.2946 (5)	0.2695 (2)	0.52140 (14)	0.0703 (9)
H13A	0.2596	0.2888	0.4716	0.084*
H13B	0.3950	0.3057	0.5287	0.084*
C14	0.2687 (13)	−0.3314 (8)	0.3851 (5)	0.078 (3)	0.701 (10)
H14A	0.1642	−0.3603	0.3914	0.093*	0.701 (10)
H14B	0.2774	−0.2968	0.3359	0.093*	0.701 (10)
C15	0.3741 (12)	−0.4272 (4)	0.3923 (3)	0.099 (3)	0.701 (10)
H15A	0.3464	−0.4884	0.3567	0.119*	0.701 (10)
H15B	0.4764	−0.3991	0.3795	0.119*	0.701 (10)
O3	0.3791 (8)	−0.4783 (4)	0.4637 (3)	0.0897 (16)	0.701 (10)
C16	0.4171 (8)	−0.3914 (4)	0.5164 (3)	0.0720 (15)	0.701 (10)
H16A	0.5182	−0.3592	0.5052	0.086*	0.701 (10)
H16B	0.4214	−0.4274	0.5654	0.086*	0.701 (10)
C17	0.3037 (12)	−0.2952 (7)	0.5166 (4)	0.071 (2)	0.701 (10)
H17A	0.3314	−0.2358	0.5534	0.086*	0.701 (10)
H17B	0.2026	−0.3261	0.5288	0.086*	0.701 (10)
C14A	0.305 (5)	−0.314 (2)	0.3745 (16)	0.158 (16)	0.299 (10)
H14C	0.4099	−0.3356	0.3611	0.189*	0.299 (10)
H14D	0.2568	−0.2740	0.3328	0.189*	0.299 (10)
C15A	0.214 (3)	−0.4207 (11)	0.3988 (7)	0.104 (7)	0.299 (10)
H15C	0.1068	−0.3977	0.4042	0.124*	0.299 (10)
H15D	0.2192	−0.4807	0.3601	0.124*	0.299 (10)
O3A	0.265 (3)	−0.4716 (10)	0.4665 (7)	0.123 (7)	0.299 (10)
C16A	0.273 (5)	−0.3884 (12)	0.5234 (7)	0.147 (13)	0.299 (10)
H16C	0.3127	−0.4283	0.5672	0.177*	0.299 (10)
H16D	0.1688	−0.3632	0.5348	0.177*	0.299 (10)
C17A	0.368 (4)	−0.279 (2)	0.5111 (16)	0.128 (13)	0.299 (10)
H17C	0.3526	−0.2209	0.5502	0.154*	0.299 (10)
H17D	0.4765	−0.2975	0.5066	0.154*	0.299 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1290 (18)	0.0440 (8)	0.0412 (9)	0.0023 (12)	−0.0188 (11)	−0.0017 (7)
O2	0.0994 (15)	0.0550 (10)	0.0481 (9)	0.0018 (11)	0.0051 (10)	−0.0090 (8)
N1	0.0788 (16)	0.0392 (9)	0.0457 (10)	0.0056 (10)	−0.0109 (11)	−0.0036 (8)
N2	0.0933 (18)	0.0368 (9)	0.0456 (11)	0.0045 (11)	−0.0062 (12)	−0.0008 (8)
N3	0.0768 (15)	0.0358 (8)	0.0387 (9)	0.0018 (11)	−0.0034 (10)	−0.0004 (7)
N4	0.132 (2)	0.0381 (10)	0.0388 (11)	0.0057 (13)	−0.0024 (13)	−0.0010 (8)
N5	0.132 (2)	0.0355 (10)	0.0535 (12)	0.0106 (13)	−0.0188 (15)	−0.0033 (9)
C1	0.082 (2)	0.0453 (11)	0.0325 (10)	0.0048 (14)	−0.0042 (12)	−0.0001 (9)
C2	0.069 (2)	0.073 (2)	0.0656 (18)	0.0070 (16)	−0.0059 (15)	0.0014 (16)
C3	0.091 (2)	0.077 (2)	0.068 (2)	−0.020 (2)	0.0049 (17)	0.0118 (17)
C4	0.124 (3)	0.0561 (15)	0.0506 (14)	0.003 (2)	−0.0017 (19)	0.0153 (12)
C5	0.087 (2)	0.074 (2)	0.083 (2)	0.0228 (19)	−0.0038 (17)	0.0235 (18)
C6	0.0678 (19)	0.073 (2)	0.0654 (18)	−0.0020 (16)	−0.0034 (14)	0.0142 (16)
C7	0.0647 (16)	0.0413 (11)	0.0402 (11)	0.0033 (12)	−0.0062 (11)	−0.0020 (9)
C8	0.0754 (18)	0.0386 (11)	0.0490 (13)	0.0083 (13)	−0.0081 (13)	−0.0040 (10)
C9	0.0766 (17)	0.0369 (10)	0.0403 (11)	0.0040 (12)	0.0015 (12)	−0.0008 (9)
C10	0.130 (3)	0.0500 (13)	0.0435 (13)	0.0165 (18)	−0.0122 (17)	−0.0005 (11)
C11	0.117 (3)	0.0575 (15)	0.0458 (13)	−0.0086 (18)	0.0039 (16)	0.0026 (11)
C12	0.102 (2)	0.0504 (13)	0.0623 (16)	0.0093 (16)	−0.0080 (16)	−0.0036 (13)
C13	0.125 (3)	0.0349 (11)	0.0510 (14)	0.0004 (15)	0.0050 (17)	−0.0031 (10)
C14	0.148 (6)	0.032 (3)	0.054 (3)	−0.004 (3)	−0.041 (4)	0.001 (2)
C15	0.186 (8)	0.050 (3)	0.062 (3)	0.038 (4)	−0.004 (4)	−0.005 (2)
O3	0.159 (5)	0.0407 (18)	0.070 (2)	0.024 (3)	−0.001 (3)	0.0062 (15)
C16	0.102 (4)	0.048 (2)	0.066 (3)	0.003 (3)	−0.011 (3)	0.011 (2)
C17	0.127 (7)	0.036 (3)	0.051 (3)	−0.001 (4)	−0.011 (4)	0.000 (2)
C14A	0.33 (4)	0.042 (9)	0.106 (15)	−0.014 (15)	0.073 (19)	−0.017 (9)
C15A	0.18 (2)	0.054 (7)	0.077 (8)	−0.033 (10)	0.003 (10)	−0.002 (6)
O3A	0.26 (2)	0.037 (4)	0.076 (6)	−0.022 (9)	−0.014 (12)	0.005 (4)
C16A	0.34 (4)	0.059 (8)	0.046 (6)	−0.057 (16)	0.001 (13)	0.005 (5)
C17A	0.19 (3)	0.055 (9)	0.135 (18)	−0.042 (13)	−0.100 (19)	0.032 (9)

Geometric parameters (Å, º) top

O1—C7	1.358 (3)	C11—H11A	0.9700
O1—C1	1.397 (3)	C11—H11B	0.9700
O2—C11	1.415 (3)	C12—C13	1.481 (4)
O2—C12	1.418 (3)	C12—H12A	0.9700
N1—C7	1.315 (3)	C12—H12B	0.9700
N1—C8	1.340 (3)	C13—H13A	0.9700
N2—C8	1.334 (3)	C13—H13B	0.9700
N2—C9	1.339 (3)	C14—C15	1.420 (11)
N3—C7	1.307 (3)	C14—H14A	0.9700
N3—C9	1.356 (3)	C14—H14B	0.9700
N4—C9	1.333 (3)	C15—O3	1.407 (7)
N4—C10	1.457 (3)	C15—H15A	0.9700
N4—C13	1.463 (3)	C15—H15B	0.9700
N5—C8	1.352 (3)	O3—C16	1.401 (7)
N5—C17A	1.45 (3)	C16—C17	1.463 (11)
N5—C14A	1.45 (3)	C16—H16A	0.9700
N5—C14	1.460 (9)	C16—H16B	0.9700
N5—C17	1.485 (9)	C17—H17A	0.9700
C1—C2	1.357 (4)	C17—H17B	0.9700
C1—C6	1.368 (4)	C14A—C15A	1.50 (3)
C2—C3	1.381 (4)	C14A—H14C	0.9700
C2—H2	0.9300	C14A—H14D	0.9700
C3—C4	1.351 (5)	C15A—O3A	1.415 (19)
C3—H3	0.9300	C15A—H15C	0.9700
C4—C5	1.357 (5)	C15A—H15D	0.9700
C4—H4	0.9300	O3A—C16A	1.389 (17)
C5—C6	1.378 (4)	C16A—C17A	1.49 (3)
C5—H5	0.9300	C16A—H16C	0.9700
C6—H6	0.9300	C16A—H16D	0.9700
C10—C11	1.483 (4)	C17A—H17C	0.9700
C10—H10A	0.9700	C17A—H17D	0.9700
C10—H10B	0.9700

C7—O1—C1	119.79 (17)	C13—C12—H12B	109.2
C11—O2—C12	109.3 (2)	H12A—C12—H12B	107.9
C7—N1—C8	112.24 (19)	N4—C13—C12	109.6 (2)
C8—N2—C9	114.4 (2)	N4—C13—H13A	109.7
C7—N3—C9	112.42 (18)	C12—C13—H13A	109.7
C9—N4—C10	123.4 (2)	N4—C13—H13B	109.7
C9—N4—C13	123.5 (2)	C12—C13—H13B	109.7
C10—N4—C13	113.1 (2)	H13A—C13—H13B	108.2
C8—N5—C17A	116.9 (10)	C15—C14—N5	109.9 (5)
C8—N5—C14A	115.2 (12)	C15—C14—H14A	109.7
C17A—N5—C14A	122.7 (18)	N5—C14—H14A	109.7
C8—N5—C14	124.4 (4)	C15—C14—H14B	109.7
C17A—N5—C14	118.1 (11)	N5—C14—H14B	109.7
C8—N5—C17	123.4 (3)	H14A—C14—H14B	108.2
C14A—N5—C17	121.4 (12)	O3—C15—C14	114.3 (6)
C14—N5—C17	110.3 (5)	O3—C15—H15A	108.7
C2—C1—C6	121.5 (2)	C14—C15—H15A	108.7
C2—C1—O1	120.0 (3)	O3—C15—H15B	108.7
C6—C1—O1	118.3 (3)	C14—C15—H15B	108.7
C1—C2—C3	118.5 (3)	H15A—C15—H15B	107.6
C1—C2—H2	120.7	C16—O3—C15	109.9 (4)
C3—C2—H2	120.7	O3—C16—C17	111.0 (5)
C4—C3—C2	121.0 (3)	O3—C16—H16A	109.4
C4—C3—H3	119.5	C17—C16—H16A	109.4
C2—C3—H3	119.5	O3—C16—H16B	109.4
C3—C4—C5	119.8 (3)	C17—C16—H16B	109.4
C3—C4—H4	120.1	H16A—C16—H16B	108.0
C5—C4—H4	120.1	C16—C17—N5	108.0 (6)
C4—C5—C6	120.6 (3)	C16—C17—H17A	110.1
C4—C5—H5	119.7	N5—C17—H17A	110.1
C6—C5—H5	119.7	C16—C17—H17B	110.1
C1—C6—C5	118.6 (3)	N5—C17—H17B	110.1
C1—C6—H6	120.7	H17A—C17—H17B	108.4
C5—C6—H6	120.7	N5—C14A—C15A	102 (2)
N3—C7—N1	129.8 (2)	N5—C14A—H14C	111.5
N3—C7—O1	118.40 (19)	C15A—C14A—H14C	111.5
N1—C7—O1	111.74 (18)	N5—C14A—H14D	111.5
N2—C8—N1	126.0 (2)	C15A—C14A—H14D	111.5
N2—C8—N5	117.2 (2)	H14C—C14A—H14D	109.3
N1—C8—N5	116.8 (2)	O3A—C15A—C14A	114.1 (18)
N4—C9—N2	117.6 (2)	O3A—C15A—H15C	108.7
N4—C9—N3	117.40 (19)	C14A—C15A—H15C	108.7
N2—C9—N3	125.0 (2)	O3A—C15A—H15D	108.7
N4—C10—C11	109.4 (3)	C14A—C15A—H15D	108.7
N4—C10—H10A	109.8	H15C—C15A—H15D	107.6
C11—C10—H10A	109.8	C16A—O3A—C15A	112.2 (12)
N4—C10—H10B	109.8	O3A—C16A—C17A	118.2 (19)
C11—C10—H10B	109.8	O3A—C16A—H16C	107.7
H10A—C10—H10B	108.2	C17A—C16A—H16C	107.7
O2—C11—C10	112.6 (3)	O3A—C16A—H16D	107.7
O2—C11—H11A	109.1	C17A—C16A—H16D	107.7
C10—C11—H11A	109.1	H16C—C16A—H16D	107.1
O2—C11—H11B	109.1	N5—C17A—C16A	98.9 (19)
C10—C11—H11B	109.1	N5—C17A—H17C	112.0
H11A—C11—H11B	107.8	C16A—C17A—H17C	112.0
O2—C12—C13	111.9 (3)	N5—C17A—H17D	112.0
O2—C12—H12A	109.2	C16A—C17A—H17D	112.0
C13—C12—H12A	109.2	H17C—C17A—H17D	109.7
O2—C12—H12B	109.2

C7—O1—C1—C2	80.8 (3)	C7—N3—C9—N4	179.8 (3)
C7—O1—C1—C6	−104.8 (3)	C7—N3—C9—N2	−0.2 (4)
C6—C1—C2—C3	0.2 (4)	C9—N4—C10—C11	−131.2 (3)
O1—C1—C2—C3	174.4 (2)	C13—N4—C10—C11	51.6 (4)
C1—C2—C3—C4	0.4 (5)	C12—O2—C11—C10	60.2 (4)
C2—C3—C4—C5	−0.9 (5)	N4—C10—C11—O2	−55.6 (4)
C3—C4—C5—C6	0.7 (5)	C11—O2—C12—C13	−60.3 (4)
C2—C1—C6—C5	−0.4 (4)	C9—N4—C13—C12	130.6 (3)
O1—C1—C6—C5	−174.7 (3)	C10—N4—C13—C12	−52.2 (4)
C4—C5—C6—C1	−0.1 (5)	O2—C12—C13—N4	56.2 (4)
C9—N3—C7—N1	2.3 (4)	C8—N5—C14—C15	141.3 (6)
C9—N3—C7—O1	−179.0 (3)	C17A—N5—C14—C15	−30 (2)
C8—N1—C7—N3	−1.8 (5)	C14A—N5—C14—C15	81 (6)
C8—N1—C7—O1	179.4 (2)	C17—N5—C14—C15	−53.9 (11)
C1—O1—C7—N3	6.1 (4)	N5—C14—C15—O3	54.9 (11)
C1—O1—C7—N1	−174.9 (3)	C14—C15—O3—C16	−57.8 (9)
C9—N2—C8—N1	2.6 (4)	C15—O3—C16—C17	59.7 (8)
C9—N2—C8—N5	−177.5 (3)	O3—C16—C17—N5	−59.9 (8)
C7—N1—C8—N2	−0.9 (4)	C8—N5—C17—C16	−138.5 (5)
C7—N1—C8—N5	179.1 (3)	C17A—N5—C17—C16	−58 (3)
C17A—N5—C8—N2	−15.7 (17)	C14A—N5—C17—C16	43 (2)
C14A—N5—C8—N2	−171.2 (19)	C14—N5—C17—C16	56.5 (9)
C14—N5—C8—N2	173.0 (7)	C8—N5—C14A—C15A	−144.3 (15)
C17—N5—C8—N2	10.1 (7)	C17A—N5—C14A—C15A	62 (3)
C17A—N5—C8—N1	164.2 (16)	C14—N5—C14A—C15A	−17 (4)
C14A—N5—C8—N1	8.8 (19)	C17—N5—C14A—C15A	34 (3)
C14—N5—C8—N1	−7.1 (7)	N5—C14A—C15A—O3A	−52 (3)
C17—N5—C8—N1	−169.9 (5)	C14A—C15A—O3A—C16A	53 (3)
C10—N4—C9—N2	2.0 (5)	C15A—O3A—C16A—C17A	−55 (3)
C13—N4—C9—N2	178.9 (3)	C8—N5—C17A—C16A	146.4 (17)
C10—N4—C9—N3	−177.9 (3)	C14A—N5—C17A—C16A	−60 (4)
C13—N4—C9—N3	−1.0 (5)	C14—N5—C17A—C16A	−42 (3)
C8—N2—C9—N4	178.1 (3)	C17—N5—C17A—C16A	34 (2)
C8—N2—C9—N3	−1.9 (4)	O3A—C16A—C17A—N5	52 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N2	0.97	2.33	2.755 (3)	106
C13—H13A···N3	0.97	2.34	2.764 (3)	106
C14—H14B···N1	0.97	2.39	2.784 (9)	104
C17—H17A···N2	0.97	2.39	2.789 (9)	104

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₅O₃
M_r	343.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	8.6788 (5), 11.2461 (5), 17.9778 (10)
V (Å³)	1754.68 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	18679, 2028, 1613
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.05
No. of reflections	2028
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C10—H10B···N2	0.97	2.33	2.755 (3)	106
C13—H13A···N3	0.97	2.34	2.764 (3)	106
C14—H14B···N1	0.97	2.39	2.784 (9)	104
C17—H17A···N2	0.97	2.39	2.789 (9)	104

Acknowledgements

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

References

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