3-Ethyl-4-[3-(1H-imidazol-1-yl)prop­yl]-5-phenyl-4H-1,2,4-triazole dihydrate

Gurumoorthy, A.; Gopalsamy, V.; Ünlüer, D.; Düğdü, E.; Varghesee, B.

doi:10.1107/S160053681003936X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2777-o2778

https://doi.org/10.1107/S160053681003936X

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3-Ethyl-4-[3-(1H-imidazol-1-yl)propyl]-5-phenyl-4H-1,2,4-triazole dihydrate

Anuradha Gurumoorthy,^a Vasuki Gopalsamy,^b ^* Dilek Ünlüer,^c Esra Düğdü ^c and Babu Varghesee ^d

^aDepartment of Physics, Saveetha School of Engineering, Saveetha University, Chennai-5, India, ^bDepartment of Physics, Kunthavai Naachiar Government Arts College for Women (Autonomous), Thanjavur 7, India, ^cDepartment of Chemistry, Faculty of Arts and Sciences, Karadeniz Teknik University, Trabzon 61080, Turkey, and ^dSophisticated Analytical Instrumentation Facilities, Indian Institute of Technology, Madras, Chennai 36, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 23 September 2010; accepted 1 October 2010; online 9 October 2010)

In the title compound, C₁₆H₁₉N₅·2H₂O, the triazole ring makes dihedral angles of 70.61 (6) and 41.89 (8)°, respectively, with the imidazole and benzene rings. The water molecules are involved in intermolecular O—H⋯N and O—H⋯O hydrogen bonds, which stabilize the crystal packing.

Related literature

For a related structure, see: Rizzoli et al. (2009 ); Kalkan et al. (2007 ). For bond lengths and angles in triazole rings, see: Thenmozhi et al. (2010 ); Rizzoli et al. (2009); Dolzhenko et al. (2010 ); Ocak Ískeleli et al. (2005 ); Ünver et al. (2010 ). For the biological activity of triazole Schiff bases, see: Thenmozhi et al. (2010) and of 1,2,4-triazole derivatives, see: Ünver et al. (2010). For the search for and synthesis of new antibiotics, see: Köysal et al. (2006 ). For the synthesis, see: Ünver et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₉N₅·2H₂O
M_r = 317.39
Monoclinic, P 2₁ /c
a = 11.0787 (16) Å
b = 9.8428 (8) Å
c = 16.3289 (18) Å
β = 105.602 (9)°
V = 1715.0 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan North et al. (1968 ) T_min = 0.821, T_max = 0.876
3030 measured reflections
2868 independent reflections
2166 reflections with I > 2σ(I)
R_int = 0.029
2 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.123
S = 1.08
2868 reflections
226 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C7—N1	1.308 (2)
C7—N3	1.373 (2)
C8—N2	1.312 (2)
C8—N3	1.363 (2)
N1—N2	1.387 (2)

C8—N3—C7	105.09 (14)
C8—N3—C11	126.52 (14)
C7—N3—C11	128.05 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.91 (1)	1.98 (1)	2.882 (3)	172 (3)
O1—H1B⋯N2ⁱ	0.90 (1)	2.02 (1)	2.913 (2)	170 (3)
O2—H2A⋯N5ⁱⁱ	0.91 (1)	1.95 (1)	2.859 (3)	176 (2)
O2—H2B⋯O1ⁱⁱⁱ	0.91 (1)	2.08 (2)	2.949 (3)	160 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ZORTEP (Zsolnai, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681003936X/jh2213sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003936X/jh2213Isup2.hkl

checkCIF report

Comment top

The biological importance of imidazoles and triazoles has stimulated much work on these heterocycles. 1,2,4-Triazole is a basic aromatic ring and possesses good coordination ability due to the presence of nitrogen atoms (Thenmozhi et al.,2010). 1,2,4-Triazole compounds posses important pharmacology activities such as antifungal and antiviral activities. Examples of such compounds bearing the 1,2,4-Triazole residues are fluconazole, the powerful azole antifungal agent as well as the potent antiviral N-nucleoside ribavirin. Furthermore various 1,2,4-Triazole derivatives have been reported as fungicidal, insecticidal, antimicrobial as well as anticonvulsants, antidepressants and plant growth regulator anticoagulants (Ünver et al., 2010). 1,2,4-Triazole derivatives are also used to build polymetallic complexes. Compounds derived from triazole possess antimicrobial, analgesic, anti-inflammatory, local anesthetic, antineoplastic and antimalarial properties. Some triazole Schiff bases also exhibit antiproliferative and anticancer activities (Thenmozhi et al., 2010). 1,2,4-Triazole moieties interact strongly with heme iron and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, it was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatese inhibitors very useful for preventing breast cancer (Ünver et al., 2010). Some of the azole derivatives used as common antibiotics, such as amphotericin B, exhibit toxic effects on humans along with antimicrobial effects. Although different antimicrobial agents are used in the treatment of microbial infections, an increasing resistance to these drugs is observed. Therefore, the search for and synthesis of new antibiotics different from commonly used ones is of current importance (Köysal et al., 2006). In a search for new triazole compounds with better biological activity, the title compound (I), was synthesized. We report here the crystal structure of the title compound, (I) (Fig.1), a new 1,2,4-triazole derivative. The compound (I) crystallizes as a dihydrate, the bond lengths and angles (Table 1) are generally normal in the triazole ring (Thenmozhi et al., 2010; Rizzoli et al., 2009; Dolzhenko et al., 2010; Ocak Ískeleli et al., 2005; Ünver et al., 2010). Atom N3 has a trigonal configuration, the sum of the three bond angles around them being 360° (Kalkan et al., 2007). The dihedral angles between the planes A(N1/N2/C7/N3/C8), B(N4/C14/N5/C15/C16) and C(C1/C2/C3/C4/C5/C6) are A/B = 70.61 (6)°, A/C = 41.89 (8)° and B/C = 68.16 (7)°. The triazole ring is essentially planar with r.m.s deviation of 0.0046Å (Dolzhenko et al., 2010). The C—N bond lengths in the triazole ring of all molecules lie in the range of 1.260 (3)–1.349 (4) Å. These are longer than a typical double C═ N bond [1.269 (2) Å], but shorter than a C—N single bond [1.443 (4) Å], (Thenmozhi et al., 2010) indicating the possibility of electron delocalization. The N3–C11–C12–C13 torsion angle of 172.00 (15)° indicates that the triazole ring and the imidazole moiety has an E-configuration across the C11–C12 bond. This configuration is stabilized by an intramolecular C11–H11···N4 hydrogen bond with H11···N4 distance of 2.54 Å. The uncoordinated water molecules are involved in intermolecular O–H···O and O–H···N hydrogen bonds (Table 2), which stabilize the crystal packing.

Related literature top

For a related structure, see: Rizzoli et al. (2009); Kalkan et al. (2007). For bond lengths and angles in triazole rings, see: Thenmozhi et al. (2010); Rizzoli et al. (2009); Dolzhenko et al. (2010); Ocak Ískeleli et al. (2005); Ünver et al. (2010). For the biological activity of triazole Schiff bases, see: Thenmozhi et al. (2010) and of 1,2,4-Triazole derivatives, see: Ünver et al. ( 2010). For the search for and synthesis of new antibiotics, see: Köysal et al. (2006). For the synthesis, see: Ünver et al. (2009).

Experimental top

The compound was synthesized by published method (Ünver et al., 2009).

Structure description top

For a related structure, see: Rizzoli et al. (2009); Kalkan et al. (2007). For bond lengths and angles in triazole rings, see: Thenmozhi et al. (2010); Rizzoli et al. (2009); Dolzhenko et al. (2010); Ocak Ískeleli et al. (2005); Ünver et al. (2010). For the biological activity of triazole Schiff bases, see: Thenmozhi et al. (2010) and of 1,2,4-Triazole derivatives, see: Ünver et al. ( 2010). For the search for and synthesis of new antibiotics, see: Köysal et al. (2006). For the synthesis, see: Ünver et al. (2009).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the a axiS. Intermolecular O—H···O and O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 3. Crystal Packing of the title compound with hydrogen bonds.

3-Ethyl-4-[3-(1H-imidazol-1-yl)propyl]-5-phenyl-4H-1,2,4-triazole dihydrate top

Crystal data top

C₁₆H₁₉N₅·2H₂O	F(000) = 680
M_r = 317.39	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
a = 11.0787 (16) Å	Cell parameters from 25 reflections
b = 9.8428 (8) Å	θ = 20–30°
c = 16.3289 (18) Å	µ = 0.68 mm⁻¹
β = 105.602 (9)°	T = 293 K
V = 1715.0 (3) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 Diffractometer	2166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 64.9°, θ_min = 4.1°
ω–2τ scan	h = 0→13
Absorption correction: ψ scan North et al. (1968)	k = 0→11
T_min = 0.821, T_max = 0.876	l = −19→18
3030 measured reflections	2 standard reflections every 60 min
2868 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0676P)² + 0.2107P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2868 reflections	Δρ_max = 0.19 e Å⁻³
226 parameters	Δρ_min = −0.18 e Å⁻³
6 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0246 (12)

Crystal data top

C₁₆H₁₉N₅·2H₂O	V = 1715.0 (3) Å³
M_r = 317.39	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.0787 (16) Å	µ = 0.68 mm⁻¹
b = 9.8428 (8) Å	T = 293 K
c = 16.3289 (18) Å	0.30 × 0.20 × 0.20 mm
β = 105.602 (9)°

Data collection top

Enraf–Nonius CAD-4 Diffractometer	2166 reflections with I > 2σ(I)
Absorption correction: ψ scan North et al. (1968)	R_int = 0.029
T_min = 0.821, T_max = 0.876	2 standard reflections every 60 min
3030 measured reflections	intensity decay: none
2868 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	6 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.19 e Å⁻³
2868 reflections	Δρ_min = −0.18 e Å⁻³
226 parameters

Special details top

Experimental. Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	1.10619 (16)	0.09615 (18)	0.08555 (11)	0.0519 (4)
H1	1.0554	0.0218	0.0878	0.062*
C2	1.23425 (18)	0.0845 (2)	0.11690 (12)	0.0609 (5)
H2	1.2692	0.0026	0.1400	0.073*
C3	1.31051 (18)	0.1935 (2)	0.11417 (12)	0.0655 (6)
H3	1.3970	0.1855	0.1354	0.079*
C4	1.25803 (18)	0.3152 (2)	0.07964 (12)	0.0623 (5)
H4	1.3094	0.3893	0.0779	0.075*
C5	1.13010 (17)	0.32727 (17)	0.04779 (11)	0.0509 (4)
H5	1.0956	0.4092	0.0242	0.061*
C6	1.05207 (15)	0.21742 (16)	0.05067 (10)	0.0429 (4)
C7	0.91650 (15)	0.23322 (16)	0.01343 (10)	0.0430 (4)
C8	0.71432 (16)	0.23090 (19)	−0.00821 (11)	0.0529 (5)
C9	0.58650 (18)	0.2091 (3)	0.00312 (15)	0.0772 (6)
H9A	0.5689	0.1124	0.0005	0.093*
H9B	0.5856	0.2406	0.0592	0.093*
C10	0.4853 (2)	0.2794 (3)	−0.06124 (19)	0.1100 (10)
H10A	0.5027	0.3750	−0.0600	0.165*
H10B	0.4066	0.2646	−0.0486	0.165*
H10C	0.4813	0.2441	−0.1167	0.165*
C11	0.83527 (17)	0.11825 (17)	0.12819 (10)	0.0496 (4)
H11A	0.7754	0.1576	0.1551	0.060*
H11B	0.9185	0.1359	0.1648	0.060*
C12	0.81484 (18)	−0.03413 (18)	0.12166 (11)	0.0571 (5)
H12A	0.8667	−0.0732	0.0884	0.069*
H12B	0.7279	−0.0529	0.0925	0.069*
C13	0.8473 (2)	−0.0997 (2)	0.20926 (13)	0.0658 (5)
H13A	0.7918	−0.0643	0.2411	0.079*
H13B	0.8335	−0.1969	0.2029	0.079*
C14	1.0814 (2)	−0.1225 (2)	0.23923 (13)	0.0618 (5)
H14	1.0804	−0.1814	0.1945	0.074*
C15	1.1436 (2)	0.0064 (2)	0.34639 (14)	0.0700 (6)
H15	1.1959	0.0543	0.3912	0.084*
C16	1.0180 (2)	0.0092 (2)	0.32597 (12)	0.0655 (5)
H16	0.9685	0.0584	0.3532	0.079*
N1	0.86819 (13)	0.29858 (15)	−0.05759 (9)	0.0524 (4)
N2	0.73910 (14)	0.29737 (16)	−0.07142 (10)	0.0572 (4)
N3	0.82282 (12)	0.18678 (13)	0.04670 (8)	0.0455 (4)
N4	0.97689 (15)	−0.07477 (15)	0.25699 (9)	0.0564 (4)
N5	1.18406 (17)	−0.07686 (18)	0.29187 (11)	0.0692 (5)
O1	0.60569 (16)	0.10016 (18)	0.26136 (10)	0.0807 (5)
O2	0.43707 (15)	−0.11055 (19)	0.28415 (13)	0.0920 (6)
H1A	0.554 (2)	0.030 (2)	0.2642 (16)	0.127 (11)*
H1B	0.650 (2)	0.121 (3)	0.3147 (9)	0.134 (11)*
H2A	0.3579 (13)	−0.096 (2)	0.2882 (17)	0.105 (9)*
H2B	0.444 (2)	−0.2016 (12)	0.277 (2)	0.154 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0520 (10)	0.0489 (10)	0.0551 (10)	−0.0035 (8)	0.0146 (8)	0.0050 (8)
C2	0.0562 (11)	0.0673 (12)	0.0575 (11)	0.0090 (9)	0.0124 (8)	0.0122 (9)
C3	0.0467 (11)	0.0881 (15)	0.0583 (11)	−0.0024 (10)	0.0086 (8)	−0.0020 (10)
C4	0.0537 (11)	0.0680 (12)	0.0668 (12)	−0.0186 (9)	0.0190 (9)	−0.0075 (10)
C5	0.0543 (11)	0.0451 (9)	0.0560 (10)	−0.0047 (8)	0.0193 (8)	−0.0015 (8)
C6	0.0464 (10)	0.0417 (8)	0.0423 (8)	−0.0029 (7)	0.0152 (7)	−0.0023 (7)
C7	0.0455 (9)	0.0376 (8)	0.0483 (9)	−0.0039 (7)	0.0169 (7)	−0.0005 (7)
C8	0.0472 (10)	0.0528 (10)	0.0598 (10)	−0.0034 (8)	0.0163 (8)	0.0020 (8)
C9	0.0505 (12)	0.0929 (16)	0.0929 (15)	−0.0052 (11)	0.0271 (11)	0.0124 (13)
C10	0.0514 (14)	0.151 (3)	0.131 (2)	0.0045 (15)	0.0297 (14)	0.031 (2)
C11	0.0578 (10)	0.0464 (9)	0.0489 (9)	−0.0042 (8)	0.0218 (8)	−0.0010 (7)
C12	0.0665 (12)	0.0479 (10)	0.0615 (11)	−0.0122 (8)	0.0252 (9)	−0.0007 (8)
C13	0.0780 (14)	0.0530 (11)	0.0757 (13)	−0.0041 (10)	0.0366 (11)	0.0124 (10)
C14	0.0839 (15)	0.0492 (10)	0.0594 (11)	0.0147 (10)	0.0314 (11)	0.0078 (9)
C15	0.0886 (16)	0.0605 (12)	0.0631 (12)	0.0040 (11)	0.0240 (11)	0.0049 (10)
C16	0.0951 (16)	0.0532 (11)	0.0590 (11)	0.0097 (10)	0.0394 (11)	0.0041 (9)
N1	0.0461 (8)	0.0548 (9)	0.0562 (8)	−0.0011 (7)	0.0137 (6)	0.0098 (7)
N2	0.0439 (9)	0.0624 (9)	0.0638 (9)	−0.0005 (7)	0.0121 (7)	0.0096 (8)
N3	0.0477 (8)	0.0424 (7)	0.0485 (7)	−0.0045 (6)	0.0163 (6)	0.0002 (6)
N4	0.0741 (11)	0.0474 (8)	0.0559 (8)	0.0066 (7)	0.0314 (8)	0.0092 (7)
N5	0.0786 (12)	0.0630 (11)	0.0704 (10)	0.0143 (9)	0.0278 (9)	0.0130 (9)
O1	0.0767 (11)	0.0899 (12)	0.0706 (10)	−0.0057 (9)	0.0114 (8)	0.0019 (8)
O2	0.0619 (10)	0.0805 (12)	0.1268 (15)	0.0036 (8)	0.0135 (9)	−0.0038 (10)

Geometric parameters (Å, º) top

C1—C2	1.377 (2)	C11—N3	1.465 (2)
C1—C6	1.387 (2)	C11—C12	1.516 (2)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.373 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—C13	1.522 (3)
C3—C4	1.384 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.377 (3)	C13—N4	1.459 (2)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.393 (2)	C13—H13B	0.9700
C5—H5	0.9300	C14—N5	1.307 (3)
C6—C7	1.469 (2)	C14—N4	1.352 (2)
C7—N1	1.308 (2)	C14—H14	0.9300
C7—N3	1.373 (2)	C15—C16	1.341 (3)
C8—N2	1.312 (2)	C15—N5	1.371 (3)
C8—N3	1.363 (2)	C15—H15	0.9300
C8—C9	1.492 (3)	C16—N4	1.372 (2)
C9—C10	1.485 (3)	C16—H16	0.9300
C9—H9A	0.9700	N1—N2	1.387 (2)
C9—H9B	0.9700	O1—H1A	0.906 (10)
C10—H10A	0.9600	O1—H1B	0.902 (10)
C10—H10B	0.9600	O2—H2A	0.909 (9)
C10—H10C	0.9600	O2—H2B	0.910 (10)

C2—C1—C6	120.80 (16)	N3—C11—H11A	108.6
C2—C1—H1	119.6	C12—C11—H11A	108.6
C6—C1—H1	119.6	N3—C11—H11B	108.6
C3—C2—C1	120.29 (18)	C12—C11—H11B	108.6
C3—C2—H2	119.9	H11A—C11—H11B	107.6
C1—C2—H2	119.9	C11—C12—C13	111.13 (15)
C2—C3—C4	119.64 (18)	C11—C12—H12A	109.4
C2—C3—H3	120.2	C13—C12—H12A	109.4
C4—C3—H3	120.2	C11—C12—H12B	109.4
C5—C4—C3	120.35 (18)	C13—C12—H12B	109.4
C5—C4—H4	119.8	H12A—C12—H12B	108.0
C3—C4—H4	119.8	N4—C13—C12	112.37 (15)
C4—C5—C6	120.35 (17)	N4—C13—H13A	109.1
C4—C5—H5	119.8	C12—C13—H13A	109.1
C6—C5—H5	119.8	N4—C13—H13B	109.1
C1—C6—C5	118.56 (16)	C12—C13—H13B	109.1
C1—C6—C7	122.80 (14)	H13A—C13—H13B	107.9
C5—C6—C7	118.59 (15)	N5—C14—N4	112.54 (18)
N1—C7—N3	110.00 (14)	N5—C14—H14	123.7
N1—C7—C6	123.22 (14)	N4—C14—H14	123.7
N3—C7—C6	126.76 (14)	C16—C15—N5	110.43 (19)
N2—C8—N3	110.02 (15)	C16—C15—H15	124.8
N2—C8—C9	125.15 (17)	N5—C15—H15	124.8
N3—C8—C9	124.82 (17)	C15—C16—N4	106.56 (17)
C10—C9—C8	113.94 (19)	C15—C16—H16	126.7
C10—C9—H9A	108.8	N4—C16—H16	126.7
C8—C9—H9A	108.8	C7—N1—N2	107.35 (13)
C10—C9—H9B	108.8	C8—N2—N1	107.52 (13)
C8—C9—H9B	108.8	C8—N3—C7	105.09 (14)
H9A—C9—H9B	107.7	C8—N3—C11	126.52 (14)
C9—C10—H10A	109.5	C7—N3—C11	128.05 (14)
C9—C10—H10B	109.5	C14—N4—C16	105.73 (17)
H10A—C10—H10B	109.5	C14—N4—C13	127.14 (17)
C9—C10—H10C	109.5	C16—N4—C13	127.00 (17)
H10A—C10—H10C	109.5	C14—N5—C15	104.73 (18)
H10B—C10—H10C	109.5	H1A—O1—H1B	108.4 (14)
N3—C11—C12	114.56 (14)	H2A—O2—H2B	106.5 (14)

C6—C1—C2—C3	0.1 (3)	C6—C7—N3—C8	177.38 (15)
C1—C2—C3—C4	−0.1 (3)	N1—C7—N3—C11	−174.85 (15)
C2—C3—C4—C5	−0.3 (3)	C6—C7—N3—C11	3.7 (3)
C3—C4—C5—C6	0.6 (3)	C12—C11—N3—C8	84.7 (2)
C2—C1—C6—C5	0.2 (3)	C12—C11—N3—C7	−102.89 (19)
C2—C1—C6—C7	177.55 (16)	N5—C14—N4—C16	0.8 (2)
C4—C5—C6—C1	−0.5 (2)	N5—C14—N4—C13	176.98 (15)
C4—C5—C6—C7	−177.98 (15)	C15—C16—N4—C14	−0.6 (2)
C1—C6—C7—N1	−137.55 (18)	C15—C16—N4—C13	−176.81 (16)
C5—C6—C7—N1	39.8 (2)	C12—C13—N4—C14	−67.3 (2)
C1—C6—C7—N3	44.1 (2)	C12—C13—N4—C16	108.1 (2)
C5—C6—C7—N3	−138.58 (17)	N4—C14—N5—C15	−0.6 (2)
N2—C8—C9—C10	−4.5 (3)	C16—C15—N5—C14	0.2 (2)
N3—C8—C9—C10	174.1 (2)	C7—N3—C11—C12	−102.89 (19)
N3—C11—C12—C13	172.00 (15)	C6—C7—N3—C11	3.7 (3)
C11—C12—C13—N4	−58.7 (2)	C6—C7—N3—C8	177.38 (15)
N5—C15—C16—N4	0.3 (2)	N1—C7—N3—C11	−174.85 (15)
N3—C7—N1—N2	0.85 (18)	N2—C8—N3—C11	174.88 (15)
C6—C7—N1—N2	−177.79 (14)	C9—C8—N3—C11	−3.9 (3)
N3—C8—N2—N1	−0.6 (2)	C5—C6—C7—N1	39.8 (2)
C9—C8—N2—N1	178.21 (19)	N1—C7—C6—C1	−137.55 (18)
C7—N1—N2—C8	−0.15 (19)	N3—C7—C6—C1	44.1 (2)
N2—C8—N3—C7	1.09 (19)	N2—C8—C9—C10	−4.5 (3)
C9—C8—N3—C7	−177.73 (19)	C10—C9—C8—N3	174.1 (2)
N2—C8—N3—C11	174.88 (15)	N4—C13—C12—C11	−58.7 (2)
C9—C8—N3—C11	−3.9 (3)	N3—C11—C12—C13	172.00 (15)
N1—C7—N3—C8	−1.19 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.91 (1)	1.98 (1)	2.882 (3)	172 (3)
O1—H1B···N2ⁱ	0.90 (1)	2.02 (1)	2.913 (2)	170 (3)
O2—H2A···N5ⁱⁱ	0.91 (1)	1.95 (1)	2.859 (3)	176 (2)
O2—H2B···O1ⁱⁱⁱ	0.91 (1)	2.08 (2)	2.949 (3)	160 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₅·2H₂O
M_r	317.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.0787 (16), 9.8428 (8), 16.3289 (18)
β (°)	105.602 (9)
V (Å³)	1715.0 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 Diffractometer
Absorption correction	ψ scan North et al. (1968)
T_min, T_max	0.821, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	3030, 2868, 2166
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.123, 1.08
No. of reflections	2868
No. of parameters	226
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ZORTEP (Zsolnai, 1997).

Selected geometric parameters (Å, º) top

C7—N1	1.308 (2)	C8—N3	1.363 (2)
C7—N3	1.373 (2)	N1—N2	1.387 (2)
C8—N2	1.312 (2)

C8—N3—C7	105.09 (14)	C7—N3—C11	128.05 (14)
C8—N3—C11	126.52 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.906 (10)	1.982 (11)	2.882 (3)	172 (3)
O1—H1B···N2ⁱ	0.902 (10)	2.020 (11)	2.913 (2)	170 (3)
O2—H2A···N5ⁱⁱ	0.909 (9)	1.952 (10)	2.859 (3)	176 (2)
O2—H2B···O1ⁱⁱⁱ	0.910 (10)	2.076 (15)	2.949 (3)	160 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

DÜ and ED thank the Research Fund of Karadeniz Technical University for its support of this work.

References

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