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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4,5-Di­methyl-1,2-di­phenyl-1H-imidazole monohydrate

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net

(Received 25 July 2010; accepted 28 July 2010; online 4 August 2010)

In the title compound, C17H16N2·H2O, the imidazole ring is essentially planar [maximum deviation = 0.0037 (7) Å]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7)° with the phenyl rings attached to the N and C atoms, respectively. The dihedral angle between the two phenyl rings is 75.83 (8)°. Inter­molecular O—H⋯N and O—H⋯O hydrogen bonds are found in the crystal structure.

Related literature

For related crystal structures and applications of imidazole derivatives, see: Gayathri et al. (2010a[Gayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791.],b[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16N2·H2O

  • Mr = 266.33

  • Tetragonal, I 41 /a

  • a = 25.5498 (2) Å

  • c = 9.3792 (1) Å

  • V = 6122.67 (9) Å3

  • Z = 16

  • Cu Kα radiation

  • μ = 0.57 mm−1

  • T = 295 K

  • 0.53 × 0.42 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.805, Tmax = 1.000

  • 8078 measured reflections

  • 3109 independent reflections

  • 2610 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.134

  • S = 1.08

  • 3109 reflections

  • 189 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1W⋯N3i 0.914 (18) 2.010 (18) 2.9111 (14) 168.6 (16)
O1W—H2W⋯O1Wi 0.86 (2) 2.03 (2) 2.8957 (15) 175 (2)
Symmetry code: (i) [y+{\script{1\over 4}}, -x+{\script{1\over 4}}, z+{\script{1\over 4}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

As part of our research (Gayathri et al., 2010a,b), we have synthesized the title compound (I) and report its crystal structure here.

In the title compound (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0037 (7) Å for C5]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7) ° with the phenyl ring (C11—C16) attached to N1 and the phenyl ring (C21—C26) attached to C2, respectively. The dihedral angle between the two phenyl rings is 75.83 (8) °. Intermolecular O1W—H1W···N3 and O1W—H2W···O1W hydrogen bonds are found in the crystal structure (Table 1, Fig. 2).

Related literature top

For related crystal structures and applications of imidazole derivatives, see: Gayathri et al. (2010a,b).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol), aniline (1.36 g, 15 mmol) and ammonium acetate (1.15 g, 15 mmol) in in ethanol (10 ml) was added benzaldehyde (1.5 g, 15 mmol) over about 1 h with the temperature maintained at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane:ethyl acetate as the eluent. Yield: 1.79 g (48%).

Refinement top

H1W and H2W attached to O1W were located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 – 0.96 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms. The methyl groups were found to be disordered over two positions. They were each refined as an idealized disordered methyl group.

Structure description top

As part of our research (Gayathri et al., 2010a,b), we have synthesized the title compound (I) and report its crystal structure here.

In the title compound (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0037 (7) Å for C5]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7) ° with the phenyl ring (C11—C16) attached to N1 and the phenyl ring (C21—C26) attached to C2, respectively. The dihedral angle between the two phenyl rings is 75.83 (8) °. Intermolecular O1W—H1W···N3 and O1W—H2W···O1W hydrogen bonds are found in the crystal structure (Table 1, Fig. 2).

For related crystal structures and applications of imidazole derivatives, see: Gayathri et al. (2010a,b).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.
4,5-Dimethyl-1,2-diphenyl-1H-imidazole monohydrate top
Crystal data top
C17H16N2·H2ODx = 1.156 Mg m3
Mr = 266.33Melting point: 375 K
Tetragonal, I41/aCu Kα radiation, λ = 1.54184 Å
Hall symbol: -I 4adCell parameters from 4027 reflections
a = 25.5498 (2) Åθ = 4.9–77.4°
c = 9.3792 (1) ŵ = 0.57 mm1
V = 6122.67 (9) Å3T = 295 K
Z = 16Irregular plate, colourless
F(000) = 22720.53 × 0.42 × 0.18 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3109 independent reflections
Radiation source: Enhance (Cu) X-ray Source2610 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 10.5081 pixels mm-1θmax = 77.6°, θmin = 4.9°
ω scansh = 2931
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 3131
Tmin = 0.805, Tmax = 1.000l = 611
8078 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0876P)2 + 0.4988P]
where P = (Fo2 + 2Fc2)/3
3109 reflections(Δ/σ)max = 0.001
189 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C17H16N2·H2OZ = 16
Mr = 266.33Cu Kα radiation
Tetragonal, I41/aµ = 0.57 mm1
a = 25.5498 (2) ÅT = 295 K
c = 9.3792 (1) Å0.53 × 0.42 × 0.18 mm
V = 6122.67 (9) Å3
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3109 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
2610 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 1.000Rint = 0.019
8078 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.16 e Å3
3109 reflectionsΔρmin = 0.21 e Å3
189 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
xyzUiso*/UeqOcc. (<1)
N10.00564 (4)0.01347 (4)0.24242 (9)0.0428 (3)
N30.09186 (4)0.00845 (4)0.23202 (10)0.0452 (3)
C20.04817 (4)0.01899 (5)0.23981 (11)0.0412 (3)
C40.07726 (5)0.06023 (5)0.22951 (13)0.0487 (3)
C50.02420 (5)0.06453 (5)0.23682 (13)0.0488 (3)
C110.04871 (4)0.00047 (5)0.25460 (11)0.0421 (3)
C120.07965 (5)0.00048 (6)0.13375 (13)0.0582 (5)
C130.13211 (5)0.01271 (7)0.14490 (16)0.0649 (5)
C140.15362 (5)0.02441 (7)0.27589 (17)0.0618 (4)
C150.12261 (5)0.02413 (7)0.39614 (15)0.0627 (5)
C160.06994 (5)0.01241 (6)0.38579 (12)0.0526 (4)
C210.04616 (5)0.07654 (5)0.24358 (12)0.0473 (3)
C220.01046 (6)0.10535 (6)0.16451 (16)0.0597 (4)
C230.01189 (7)0.15977 (6)0.1680 (2)0.0778 (6)
C240.04837 (8)0.18527 (7)0.2490 (2)0.0856 (7)
C250.08410 (8)0.15716 (7)0.3262 (2)0.0869 (7)
C260.08325 (6)0.10288 (6)0.32454 (17)0.0662 (5)
C410.11729 (7)0.10273 (6)0.2167 (2)0.0696 (5)
C510.01126 (7)0.11082 (6)0.2437 (2)0.0704 (5)
O1W0.24177 (4)0.04630 (4)0.44390 (11)0.0590 (3)
H120.065220.007700.045490.0699*
H130.153030.013070.063750.0779*
H140.189020.032470.283110.0742*
H150.137180.031860.484530.0753*
H160.048940.012570.466800.0631*
H220.014460.088280.109170.0716*
H230.012120.178940.114790.0933*
H240.048910.221650.251550.1027*
H250.109140.174600.380220.1043*
H260.107560.084100.377730.0794*
H41A0.151640.087520.213900.1045*0.500
H41B0.114670.125730.297330.1045*0.500
H41C0.111260.122190.130730.1045*0.500
H41D0.100070.136110.214080.1045*0.500
H41E0.137040.097900.130640.1045*0.500
H41F0.140450.101440.297240.1045*0.500
H51A0.046950.099180.247950.1055*0.500
H51B0.006340.132050.160320.1055*0.500
H51C0.003320.131020.327240.1055*0.500
H51D0.009210.142320.242390.1055*0.500
H51E0.031400.109450.330020.1055*0.500
H51F0.034420.110480.163100.1055*0.500
H1W0.2423 (7)0.0816 (7)0.4596 (18)0.064 (4)*
H2W0.2563 (9)0.0340 (9)0.520 (2)0.095 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0387 (5)0.0480 (5)0.0416 (5)0.0005 (4)0.0003 (3)0.0024 (4)
N30.0396 (5)0.0533 (5)0.0427 (4)0.0041 (4)0.0026 (4)0.0011 (4)
C20.0382 (5)0.0498 (6)0.0357 (5)0.0006 (4)0.0019 (4)0.0033 (4)
C40.0484 (6)0.0510 (6)0.0468 (6)0.0068 (5)0.0022 (5)0.0010 (5)
C50.0512 (6)0.0466 (6)0.0485 (6)0.0023 (5)0.0005 (5)0.0010 (5)
C110.0363 (5)0.0498 (6)0.0403 (5)0.0019 (4)0.0005 (4)0.0015 (4)
C120.0493 (7)0.0851 (10)0.0402 (6)0.0004 (6)0.0044 (5)0.0102 (6)
C130.0463 (7)0.0911 (10)0.0574 (7)0.0015 (6)0.0156 (6)0.0082 (7)
C140.0370 (6)0.0771 (9)0.0713 (8)0.0010 (5)0.0022 (6)0.0031 (7)
C150.0496 (7)0.0881 (10)0.0505 (7)0.0062 (6)0.0081 (5)0.0060 (7)
C160.0457 (6)0.0745 (8)0.0377 (5)0.0039 (5)0.0026 (4)0.0032 (5)
C210.0448 (6)0.0486 (6)0.0486 (6)0.0008 (4)0.0111 (5)0.0060 (5)
C220.0538 (7)0.0548 (7)0.0705 (8)0.0052 (5)0.0082 (6)0.0030 (6)
C230.0768 (10)0.0573 (8)0.0992 (12)0.0150 (7)0.0224 (9)0.0099 (8)
C240.0900 (12)0.0491 (8)0.1177 (15)0.0020 (8)0.0344 (11)0.0162 (9)
C250.0846 (12)0.0666 (10)0.1096 (14)0.0172 (9)0.0127 (11)0.0349 (10)
C260.0621 (8)0.0636 (8)0.0729 (9)0.0066 (6)0.0011 (7)0.0178 (7)
C410.0635 (8)0.0572 (8)0.0882 (10)0.0169 (6)0.0119 (8)0.0054 (7)
C510.0643 (9)0.0542 (8)0.0926 (11)0.0080 (6)0.0007 (8)0.0011 (7)
O1W0.0640 (5)0.0518 (6)0.0611 (5)0.0050 (4)0.0054 (4)0.0043 (4)
Geometric parameters (Å, º) top
O1W—H2W0.86 (2)C12—H120.9300
O1W—H1W0.914 (18)C13—H130.9300
N1—C51.3891 (16)C14—H140.9300
N1—C21.3672 (15)C15—H150.9300
N1—C111.4381 (15)C16—H160.9300
N3—C41.3748 (16)C22—H220.9300
N3—C21.3202 (15)C23—H230.9300
C2—C211.4717 (18)C24—H240.9300
C4—C411.497 (2)C25—H250.9300
C4—C51.3618 (18)C26—H260.9300
C5—C511.491 (2)C41—H41B0.9600
C11—C121.3819 (16)C41—H41A0.9600
C11—C161.3789 (16)C41—H41E0.9600
C12—C131.3803 (18)C41—H41C0.9600
C13—C141.379 (2)C41—H41D0.9600
C14—C151.378 (2)C41—H41F0.9600
C15—C161.3820 (18)C51—H51B0.9600
C21—C261.388 (2)C51—H51C0.9600
C21—C221.387 (2)C51—H51E0.9600
C22—C231.391 (2)C51—H51F0.9600
C23—C241.368 (3)C51—H51D0.9600
C24—C251.369 (3)C51—H51A0.9600
C25—C261.387 (2)
O1W···O1Wi2.8957 (15)C41···H51D2.9500
O1W···O1Wii2.8957 (15)C51···H41D2.9300
O1W···N3ii2.9111 (14)H1W···N3ii2.010 (18)
O1W···H14iii2.8200H1W···H41Aii2.4700
O1W···H2Wi2.03 (2)H1W···C4ii2.910 (18)
O1W···H13iv2.7900H1W···C2ii3.098 (18)
O1W···H15v2.7800H2W···O1Wii2.03 (2)
O1W···H41Aii2.7900H2W···H14v2.5200
O1W···H14v2.9100H12···N3vi2.7200
N3···O1Wi2.9111 (14)H12···C2vi2.7300
N1···H16v2.9400H13···O1Wviii2.7900
N1···H222.9300H14···O1Wvii2.8200
N3···H262.7600H14···O1Wv2.9100
N3···H1Wi2.010 (18)H14···H2Wv2.5200
N3···H12vi2.7200H15···O1Wv2.7800
C11···C223.191 (2)H16···C2v2.8700
C12···C223.544 (2)H16···N1v2.9400
C12···C513.493 (2)H22···N12.9300
C22···C123.544 (2)H22···C112.7700
C22···C113.191 (2)H22···C122.8000
C23···C25vii3.597 (3)H24···C24iii3.0800
C25···C23iii3.597 (3)H24···H51Ci2.5600
C51···C123.493 (2)H25···C23iii2.9600
C2···H1Wi3.098 (18)H25···C22iii3.0600
C2···H16v2.8700H26···N32.7600
C2···H12vi2.7300H41A···H1Wi2.4700
C4···H1Wi2.910 (18)H41A···O1Wi2.7900
C11···H222.7700H41B···C24ii2.9900
C11···H51A2.5500H41B···C25ii2.8600
C11···H51E2.9300H41B···C26ii2.9200
C11···H51F2.9800H41D···C512.9300
C12···H51F3.0700H41D···H51D2.3400
C12···H222.8000H41F···C26ii3.0900
C12···H51A2.8900H51A···C112.5500
C22···H25vii3.0600H51A···C122.8900
C23···H25vii2.9600H51C···C24ii2.9800
C24···H51Ci2.9800H51C···H24ii2.5600
C24···H41Bi2.9900H51D···C412.9500
C24···H24vii3.0800H51D···H41D2.3400
C25···H41Bi2.8600H51E···C112.9300
C26···H41Fi3.0900H51F···C112.9800
C26···H41Bi2.9200H51F···C123.0700
H1W—O1W—H2W102.7 (18)C26—C25—H25120.00
C2—N1—C11128.22 (10)C24—C25—H25120.00
C5—N1—C11124.42 (10)C25—C26—H26120.00
C2—N1—C5107.32 (10)C21—C26—H26120.00
C2—N3—C4106.41 (10)C4—C41—H41A109.00
N1—C2—N3110.54 (11)C4—C41—H41C109.00
N1—C2—C21125.30 (10)C4—C41—H41D109.00
N3—C2—C21124.15 (10)C4—C41—H41B109.00
N3—C4—C41120.94 (12)C4—C41—H41F109.00
C5—C4—C41128.74 (12)H41A—C41—H41B109.00
N3—C4—C5110.30 (11)H41A—C41—H41C109.00
N1—C5—C51122.40 (12)H41A—C41—H41D141.00
C4—C5—C51132.14 (13)H41A—C41—H41E56.00
N1—C5—C4105.43 (11)H41A—C41—H41F56.00
N1—C11—C16120.37 (10)C4—C41—H41E109.00
C12—C11—C16120.46 (11)H41B—C41—H41D56.00
N1—C11—C12119.16 (10)H41B—C41—H41E141.00
C11—C12—C13119.56 (12)H41B—C41—H41F56.00
C12—C13—C14120.25 (13)H41C—C41—H41D56.00
C13—C14—C15119.93 (12)H41C—C41—H41E56.00
C14—C15—C16120.22 (13)H41C—C41—H41F141.00
C11—C16—C15119.58 (11)H41D—C41—H41E109.00
C2—C21—C26118.27 (11)H41D—C41—H41F109.00
C22—C21—C26118.95 (13)H41E—C41—H41F109.00
C2—C21—C22122.71 (11)H41B—C41—H41C109.00
C21—C22—C23120.04 (14)C5—C51—H51B109.00
C22—C23—C24120.47 (16)C5—C51—H51C109.00
C23—C24—C25119.90 (17)C5—C51—H51A109.00
C24—C25—C26120.55 (17)C5—C51—H51E109.00
C21—C26—C25120.10 (15)C5—C51—H51F109.00
C13—C12—H12120.00C5—C51—H51D109.00
C11—C12—H12120.00H51A—C51—H51C109.00
C14—C13—H13120.00H51A—C51—H51D141.00
C12—C13—H13120.00H51A—C51—H51E56.00
C13—C14—H14120.00H51A—C51—H51F56.00
C15—C14—H14120.00H51B—C51—H51C109.00
C16—C15—H15120.00H51B—C51—H51D56.00
C14—C15—H15120.00H51B—C51—H51E141.00
C11—C16—H16120.00H51B—C51—H51F56.00
C15—C16—H16120.00H51C—C51—H51D56.00
C23—C22—H22120.00H51C—C51—H51E56.00
C21—C22—H22120.00H51C—C51—H51F141.00
C22—C23—H23120.00H51D—C51—H51E109.00
C24—C23—H23120.00H51D—C51—H51F109.00
C23—C24—H24120.00H51E—C51—H51F109.00
C25—C24—H24120.00H51A—C51—H51B109.00
C5—N1—C2—N30.41 (12)N3—C4—C5—N10.66 (13)
C5—N1—C2—C21179.82 (10)N3—C4—C5—C51177.15 (14)
C11—N1—C2—N3178.01 (9)C41—C4—C5—N1177.86 (13)
C11—N1—C2—C212.58 (17)C41—C4—C5—C514.3 (2)
C2—N1—C5—C40.65 (12)N1—C11—C12—C13178.61 (13)
C2—N1—C5—C51177.43 (12)C16—C11—C12—C130.2 (2)
C11—N1—C5—C4178.36 (10)N1—C11—C16—C15177.99 (13)
C11—N1—C5—C510.28 (18)C12—C11—C16—C150.4 (2)
C2—N1—C11—C12101.64 (14)C11—C12—C13—C140.6 (2)
C2—N1—C11—C1679.95 (16)C12—C13—C14—C150.3 (3)
C5—N1—C11—C1281.14 (15)C13—C14—C15—C160.3 (3)
C5—N1—C11—C1697.27 (15)C14—C15—C16—C110.7 (2)
C4—N3—C2—N10.00 (13)C2—C21—C22—C23177.34 (13)
C4—N3—C2—C21179.42 (10)C26—C21—C22—C230.5 (2)
C2—N3—C4—C50.42 (13)C2—C21—C26—C25177.29 (14)
C2—N3—C4—C41178.24 (12)C22—C21—C26—C250.3 (2)
N1—C2—C21—C2242.85 (17)C21—C22—C23—C240.0 (3)
N1—C2—C21—C26140.30 (12)C22—C23—C24—C250.6 (3)
N3—C2—C21—C22136.48 (13)C23—C24—C25—C260.8 (3)
N3—C2—C21—C2640.36 (17)C24—C25—C26—C210.4 (3)
Symmetry codes: (i) y+1/4, x1/4, z1/4; (ii) y+1/4, x+1/4, z+1/4; (iii) y+1/4, x1/4, z+3/4; (iv) y+1/4, x+1/4, z+1/4; (v) x, y, z+1; (vi) x, y, z; (vii) y1/4, x1/4, z+3/4; (viii) y1/4, x+1/4, z+1/4.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N3ii0.914 (18)2.010 (18)2.9111 (14)168.6 (16)
O1W—H2W···O1Wii0.86 (2)2.03 (2)2.8957 (15)175 (2)
Symmetry code: (ii) y+1/4, x+1/4, z+1/4.

Experimental details

Crystal data
Chemical formulaC17H16N2·H2O
Mr266.33
Crystal system, space groupTetragonal, I41/a
Temperature (K)295
a, c (Å)25.5498 (2), 9.3792 (1)
V3)6122.67 (9)
Z16
Radiation typeCu Kα
µ (mm1)0.57
Crystal size (mm)0.53 × 0.42 × 0.18
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.805, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
8078, 3109, 2610
Rint0.019
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.134, 1.08
No. of reflections3109
No. of parameters189
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N3i0.914 (18)2.010 (18)2.9111 (14)168.6 (16)
O1W—H2W···O1Wi0.86 (2)2.03 (2)2.8957 (15)175 (2)
Symmetry code: (i) y+1/4, x+1/4, z+1/4.
 

Acknowledgements

JJ is thankful to the Department of Science and Technology (No. SR/S1/IC-07/2007) and the University Grants Commission [F. No. 36–21/2008 (SR)] for providing funds for this research. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds