2,6-Bis(3-phenyl-1H-pyrazol-5-yl)pyridine monohydrate

Dong, J.-Y.; You, T.-P.

doi:10.1107/S1600536808008520

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o820

doi:10.1107/S1600536808008520

Open

access

2,6-Bis(3-phenyl-1H-pyrazol-5-yl)pyridine monohydrate

Jian-Yu Dong ^a and Tian-Pa You ^a ^*

^aDepartment of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China
^*Correspondence e-mail: jianyud@mail.ustc.edu.cn

(Received 16 February 2008; accepted 31 March 2008; online 10 April 2008)

In the title compound, C₂₃H₁₇N₅·H₂O, the pyrazole rings are slightly twisted from the central pyridine ring, forming dihedral angles of 5.3 (2) and 3.5 (2)°. The pyrazole and phenyl rings on each side of the pyridine ring are also approximately coplanar, making dihedral angles of 6.0 (2) and 4.5 (2)°. In the crystal structure, 2,6-bis(3-phenyl-1H-pyrazol-5-yl)pyridine and water molecules are linked together via N—H⋯O and O—H⋯N hydrogen bonds, forming a column running parallel to the a axis.

Related literature

For general background, see: Dias & Gamage (2007 ); Zhou & Chen (2007a ,b ); Zhang et al. (2007 ).

Experimental

Crystal data

C₂₃H₁₇N₅·H₂O
M_r = 381.43
Monoclinic, P 2₁ /n
a = 8.0581 (17) Å
b = 19.975 (2) Å
c = 12.451 (2) Å
β = 98.273 (3)°
V = 1983.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.42 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.966, T_max = 0.994
9869 measured reflections
3513 independent reflections
1796 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.159
S = 1.05
3513 reflections
271 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H22⋯N5ⁱ	0.84 (3)	2.13 (3)	2.878 (4)	148 (4)
O1—H23⋯N3ⁱⁱ	0.84 (4)	2.20 (2)	2.956 (4)	150 (4)
N2—H17⋯O1	0.86	2.07	2.918 (4)	167
N4—H5⋯O1	0.86	2.16	3.007 (4)	170
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008520/is2276sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008520/is2276Isup2.hkl

checkCIF report

Comment top

Pyrazolyl ligands are a kind of mutifuntional organic ligands often displaying exo-bidentate coordination mode (Dias & Gamage, 2007; Zhou & Chen, 2007a; Zhang et al., 2007). The title compound, 2,6-bis(3-phenyl-1H-pyrazol-5-yl)pyridine (hereinafter abbreviated to bppp), is a pincer-like bispyrazolyl ligand. As a kind of anionic multidentate linker, it is a suitable candidate to connect transition metals into aggregate (Zhou & Chen, 2007b).

As shown in Fig. 1, the asymmetric unit contains one bppp molecule and one water molecule, and they are linked together via N—H···O hydrogen bonds. The pyrazole rings are slightly twisted from the central pyridine ring with the dihedral angles of 5.3 (2) and 3.5 (2)°. The pyrazole and phenyl rings on each side of the molecule are also approximately coplanar with the dihedral angles of 6.0 (2) and 4.5 (2)°. Furthermore, O—H···N hydrogen bonds extend it in a one-dimensional chains running parallel to the a axis (Fig. 2). All bond lengths and angles in the title compound are normal.

Related literature top

For general background, see: Dias & Gamage (2007); Zhou & Chen (2007a,b); Zhang et al. (2007).

Experimental top

All reagents were of analytical grade and used without further purification. Bppp was prepared by the general procedure of Zhou and Chen (2007a). Bppp (36 mg, 0.1 mmol) in 20 ml of water in a sealed stainless vial was heated at 170 °C for 48 h. Cooling the vial slowly (1 °C/h) afforded colorless crystals. Analysis found: C 72.64, H 4.90, N 18.25%; calculated for C₂₃H₁₉N₅O: C 72.42, H 5.02, N 18.36%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A partial packing view, showing the hydrogen bonds (dashed lines).

2,6-Bis(3-phenyl-1H-pyrazol-5-yl)pyridine monohydrate top

Crystal data top

C₂₃H₁₇N₅·H₂O	F(000) = 800
M_r = 381.43	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1722 reflections
a = 8.0581 (17) Å	θ = 2.8–22.2°
b = 19.975 (2) Å	µ = 0.08 mm⁻¹
c = 12.451 (2) Å	T = 298 K
β = 98.273 (3)°	Needle, colorless
V = 1983.2 (6) Å³	0.42 × 0.11 × 0.07 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3513 independent reflections
Radiation source: fine-focus sealed tube	1796 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→9
T_min = 0.966, T_max = 0.994	k = −22→23
9869 measured reflections	l = −14→13

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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0411P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3513 reflections	Δρ_max = 0.18 e Å⁻³
271 parameters	Δρ_min = −0.18 e Å⁻³
3 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*^=kFc[1+0.001xFc^2^λ^3^/sin(2θ)]^-1/4^
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (10)

Crystal data top

C₂₃H₁₇N₅·H₂O	V = 1983.2 (6) Å³
M_r = 381.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0581 (17) Å	µ = 0.08 mm⁻¹
b = 19.975 (2) Å	T = 298 K
c = 12.451 (2) Å	0.42 × 0.11 × 0.07 mm
β = 98.273 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3513 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	1796 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.994	R_int = 0.077
9869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	3 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.18 e Å⁻³
3513 reflections	Δρ_min = −0.18 e Å⁻³
271 parameters

Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
N1	0.1701 (3)	0.11239 (13)	0.7473 (2)	0.0464 (7)
N2	0.4662 (3)	0.11019 (14)	0.8827 (2)	0.0509 (7)
H17	0.3906	0.0825	0.8969	0.061*
N3	0.6177 (3)	0.11540 (14)	0.9425 (2)	0.0510 (7)
N4	−0.0667 (3)	0.02481 (13)	0.7985 (2)	0.0489 (7)
H5	0.0272	0.0252	0.8413	0.059*
N5	−0.1970 (3)	−0.01481 (14)	0.8133 (2)	0.0535 (8)
C1	0.0274 (4)	0.10897 (16)	0.6795 (3)	0.0469 (8)
C2	−0.0007 (5)	0.14642 (18)	0.5851 (3)	0.0671 (11)
H2	−0.1022	0.1436	0.5392	0.081*
C3	0.1241 (5)	0.1876 (2)	0.5611 (3)	0.0800 (13)
H3	0.1081	0.2132	0.4981	0.096*
C4	0.2718 (5)	0.19125 (18)	0.6292 (3)	0.0705 (11)
H4	0.3580	0.2188	0.6134	0.085*
C5	0.2900 (4)	0.15272 (16)	0.7226 (3)	0.0485 (9)
C6	0.4445 (4)	0.15273 (16)	0.7981 (3)	0.0464 (8)
C7	0.5920 (4)	0.18745 (16)	0.8030 (3)	0.0491 (9)
H7	0.6173	0.2208	0.7558	0.059*
C8	0.6966 (4)	0.16260 (15)	0.8935 (3)	0.0459 (8)
C9	0.8667 (4)	0.18274 (17)	0.9361 (3)	0.0479 (9)
C10	0.9428 (5)	0.2353 (2)	0.8903 (3)	0.0759 (12)
H10	0.8857	0.2576	0.8306	0.091*
C11	1.1031 (6)	0.2547 (2)	0.9324 (4)	0.0936 (15)
H11	1.1533	0.2903	0.9013	0.112*
C12	1.1886 (5)	0.2221 (2)	1.0195 (4)	0.0860 (14)
H12	1.2972	0.2350	1.0472	0.103*
C13	1.1139 (5)	0.17056 (19)	1.0656 (4)	0.0744 (12)
H13	1.1704	0.1492	1.1265	0.089*
C14	0.9565 (4)	0.15005 (17)	1.0232 (3)	0.0607 (10)
H14	0.9091	0.1134	1.0535	0.073*
C15	−0.0992 (4)	0.06365 (16)	0.7095 (2)	0.0454 (8)
C16	−0.2579 (4)	0.04886 (16)	0.6641 (3)	0.0506 (9)
H16	−0.3166	0.0673	0.6013	0.061*
C17	−0.3159 (4)	0.00052 (17)	0.7303 (3)	0.0474 (8)
C18	−0.4788 (4)	−0.03241 (18)	0.7192 (3)	0.0510 (9)
C19	−0.6077 (4)	−0.01190 (19)	0.6401 (3)	0.0617 (10)
H19	−0.5885	0.0225	0.5930	0.074*
C20	−0.7635 (5)	−0.0415 (2)	0.6298 (3)	0.0717 (12)
H20	−0.8480	−0.0271	0.5759	0.086*
C21	−0.7945 (5)	−0.0916 (2)	0.6984 (4)	0.0772 (13)
H21	−0.9002	−0.1112	0.6919	0.093*
C22	−0.6695 (5)	−0.1130 (2)	0.7767 (3)	0.0756 (12)
H22A	−0.6894	−0.1480	0.8225	0.091*
C23	−0.5147 (5)	−0.0831 (2)	0.7880 (3)	0.0668 (11)
H23A	−0.4319	−0.0973	0.8432	0.080*
O1	0.2448 (3)	0.01202 (14)	0.9621 (2)	0.0566 (7)
H22	0.216 (6)	0.028 (2)	1.019 (2)	0.15 (2)*
H23	0.298 (6)	−0.0242 (14)	0.967 (3)	0.15 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0427 (17)	0.0464 (17)	0.0497 (16)	0.0026 (14)	0.0054 (14)	−0.0008 (13)
N2	0.0401 (18)	0.0554 (18)	0.0563 (17)	−0.0080 (14)	0.0035 (14)	0.0059 (15)
N3	0.0378 (17)	0.0568 (18)	0.0577 (17)	−0.0084 (14)	0.0040 (14)	0.0026 (14)
N4	0.0354 (17)	0.0575 (18)	0.0516 (17)	−0.0011 (14)	−0.0011 (13)	0.0039 (14)
N5	0.0397 (17)	0.0625 (19)	0.0577 (18)	−0.0063 (15)	0.0048 (15)	0.0025 (15)
C1	0.050 (2)	0.041 (2)	0.049 (2)	0.0068 (17)	0.0032 (18)	−0.0019 (16)
C2	0.063 (3)	0.059 (2)	0.071 (3)	−0.005 (2)	−0.017 (2)	0.020 (2)
C3	0.084 (3)	0.076 (3)	0.074 (3)	−0.014 (3)	−0.011 (3)	0.035 (2)
C4	0.063 (3)	0.067 (3)	0.077 (3)	−0.016 (2)	−0.006 (2)	0.026 (2)
C5	0.042 (2)	0.044 (2)	0.058 (2)	0.0012 (17)	0.0023 (18)	−0.0016 (17)
C6	0.046 (2)	0.0412 (19)	0.052 (2)	0.0007 (17)	0.0053 (17)	−0.0032 (17)
C7	0.052 (2)	0.0403 (19)	0.056 (2)	−0.0025 (17)	0.0114 (18)	0.0037 (17)
C8	0.043 (2)	0.039 (2)	0.057 (2)	−0.0035 (16)	0.0130 (18)	−0.0073 (16)
C9	0.041 (2)	0.044 (2)	0.060 (2)	−0.0072 (16)	0.0103 (18)	−0.0101 (17)
C10	0.071 (3)	0.077 (3)	0.078 (3)	−0.026 (2)	0.004 (2)	0.004 (2)
C11	0.085 (4)	0.098 (4)	0.097 (3)	−0.046 (3)	0.010 (3)	0.010 (3)
C12	0.056 (3)	0.080 (3)	0.121 (4)	−0.028 (2)	0.009 (3)	−0.009 (3)
C13	0.049 (2)	0.065 (3)	0.107 (3)	−0.005 (2)	0.001 (2)	−0.006 (2)
C14	0.044 (2)	0.048 (2)	0.087 (3)	−0.0069 (18)	0.002 (2)	0.002 (2)
C15	0.042 (2)	0.050 (2)	0.0436 (19)	0.0046 (17)	0.0033 (16)	−0.0001 (17)
C16	0.045 (2)	0.057 (2)	0.048 (2)	0.0066 (18)	−0.0010 (17)	0.0009 (18)
C17	0.038 (2)	0.055 (2)	0.049 (2)	0.0046 (17)	0.0073 (17)	−0.0090 (17)
C18	0.044 (2)	0.058 (2)	0.050 (2)	0.0012 (18)	0.0064 (17)	−0.0136 (18)
C19	0.044 (2)	0.071 (3)	0.068 (3)	0.004 (2)	0.001 (2)	−0.015 (2)
C20	0.045 (3)	0.086 (3)	0.080 (3)	0.008 (2)	−0.006 (2)	−0.030 (3)
C21	0.048 (3)	0.101 (4)	0.085 (3)	−0.015 (2)	0.019 (2)	−0.034 (3)
C22	0.058 (3)	0.096 (3)	0.073 (3)	−0.013 (2)	0.011 (2)	−0.007 (2)
C23	0.043 (2)	0.087 (3)	0.070 (3)	−0.012 (2)	0.006 (2)	−0.004 (2)
O1	0.0573 (17)	0.0555 (17)	0.0564 (16)	−0.0011 (14)	0.0067 (13)	0.0061 (13)

Geometric parameters (Å, º) top

N1—C5	1.327 (4)	C10—H10	0.9300
N1—C1	1.327 (4)	C11—C12	1.364 (6)
N2—N3	1.339 (3)	C11—H11	0.9300
N2—C6	1.344 (4)	C12—C13	1.360 (5)
N2—H17	0.8600	C12—H12	0.9300
N3—C8	1.333 (4)	C13—C14	1.365 (5)
N4—C15	1.348 (4)	C13—H13	0.9300
N4—N5	1.348 (3)	C14—H14	0.9300
N4—H5	0.8600	C15—C16	1.354 (4)
N5—C17	1.340 (4)	C16—C17	1.393 (4)
C1—C2	1.383 (4)	C16—H16	0.9300
C1—C15	1.453 (4)	C17—C18	1.457 (4)
C2—C3	1.365 (5)	C18—C23	1.383 (5)
C2—H2	0.9300	C18—C19	1.387 (4)
C3—C4	1.360 (5)	C19—C20	1.376 (5)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.385 (4)	C20—C21	1.362 (5)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.448 (4)	C21—C22	1.366 (5)
C6—C7	1.370 (4)	C21—H21	0.9300
C7—C8	1.397 (4)	C22—C23	1.372 (5)
C7—H7	0.9300	C22—H22A	0.9300
C8—C9	1.454 (4)	C23—H23A	0.9300
C9—C14	1.378 (4)	O1—H22	0.84 (3)
C9—C10	1.380 (5)	O1—H23	0.84 (4)
C10—C11	1.378 (5)

C5—N1—C1	118.5 (3)	C12—C11—H11	119.8
N3—N2—C6	113.1 (3)	C10—C11—H11	119.8
N3—N2—H17	123.5	C13—C12—C11	119.6 (4)
C6—N2—H17	123.5	C13—C12—H12	120.2
C8—N3—N2	104.9 (3)	C11—C12—H12	120.2
C15—N4—N5	112.7 (3)	C12—C13—C14	120.4 (4)
C15—N4—H5	123.6	C12—C13—H13	119.8
N5—N4—H5	123.6	C14—C13—H13	119.8
C17—N5—N4	104.2 (3)	C13—C14—C9	121.1 (4)
N1—C1—C2	122.2 (3)	C13—C14—H14	119.5
N1—C1—C15	116.4 (3)	C9—C14—H14	119.5
C2—C1—C15	121.3 (3)	N4—C15—C16	106.1 (3)
C3—C2—C1	118.4 (4)	N4—C15—C1	120.6 (3)
C3—C2—H2	120.8	C16—C15—C1	133.2 (3)
C1—C2—H2	120.8	C15—C16—C17	106.4 (3)
C4—C3—C2	120.2 (4)	C15—C16—H16	126.8
C4—C3—H3	119.9	C17—C16—H16	126.8
C2—C3—H3	119.9	N5—C17—C16	110.5 (3)
C3—C4—C5	118.1 (4)	N5—C17—C18	120.3 (3)
C3—C4—H4	120.9	C16—C17—C18	129.2 (3)
C5—C4—H4	120.9	C23—C18—C19	117.0 (3)
N1—C5—C4	122.6 (3)	C23—C18—C17	122.5 (3)
N1—C5—C6	115.9 (3)	C19—C18—C17	120.4 (3)
C4—C5—C6	121.5 (3)	C20—C19—C18	121.2 (4)
N2—C6—C7	105.7 (3)	C20—C19—H19	119.4
N2—C6—C5	120.7 (3)	C18—C19—H19	119.4
C7—C6—C5	133.5 (3)	C21—C20—C19	120.3 (4)
C6—C7—C8	106.0 (3)	C21—C20—H20	119.8
C6—C7—H7	127.0	C19—C20—H20	119.8
C8—C7—H7	127.0	C20—C21—C22	119.7 (4)
N3—C8—C7	110.3 (3)	C20—C21—H21	120.2
N3—C8—C9	121.1 (3)	C22—C21—H21	120.2
C7—C8—C9	128.6 (3)	C21—C22—C23	120.2 (4)
C14—C9—C10	118.1 (3)	C21—C22—H22A	119.9
C14—C9—C8	121.1 (3)	C23—C22—H22A	119.9
C10—C9—C8	120.8 (3)	C22—C23—C18	121.5 (4)
C11—C10—C9	120.3 (4)	C22—C23—H23A	119.2
C11—C10—H10	119.8	C18—C23—H23A	119.2
C9—C10—H10	119.8	H22—O1—H23	118 (2)
C12—C11—C10	120.4 (4)

C6—N2—N3—C8	−0.7 (4)	C9—C10—C11—C12	0.3 (7)
C15—N4—N5—C17	−0.5 (3)	C10—C11—C12—C13	−0.8 (7)
C5—N1—C1—C2	−0.7 (5)	C11—C12—C13—C14	2.1 (7)
C5—N1—C1—C15	179.4 (3)	C12—C13—C14—C9	−3.0 (6)
N1—C1—C2—C3	0.7 (6)	C10—C9—C14—C13	2.5 (5)
C15—C1—C2—C3	−179.4 (3)	C8—C9—C14—C13	−177.6 (3)
C1—C2—C3—C4	−0.1 (6)	N5—N4—C15—C16	0.1 (4)
C2—C3—C4—C5	−0.5 (6)	N5—N4—C15—C1	−179.1 (3)
C1—N1—C5—C4	0.1 (5)	N1—C1—C15—N4	−3.8 (4)
C1—N1—C5—C6	−178.2 (3)	C2—C1—C15—N4	176.4 (3)
C3—C4—C5—N1	0.6 (6)	N1—C1—C15—C16	177.3 (3)
C3—C4—C5—C6	178.7 (3)	C2—C1—C15—C16	−2.6 (6)
N3—N2—C6—C7	0.4 (4)	N4—C15—C16—C17	0.3 (4)
N3—N2—C6—C5	178.1 (3)	C1—C15—C16—C17	179.3 (3)
N1—C5—C6—N2	4.9 (4)	N4—N5—C17—C16	0.7 (3)
C4—C5—C6—N2	−173.4 (3)	N4—N5—C17—C18	−179.5 (3)
N1—C5—C6—C7	−178.1 (3)	C15—C16—C17—N5	−0.6 (4)
C4—C5—C6—C7	3.6 (6)	C15—C16—C17—C18	179.5 (3)
N2—C6—C7—C8	0.0 (3)	N5—C17—C18—C23	−4.3 (5)
C5—C6—C7—C8	−177.2 (3)	C16—C17—C18—C23	175.6 (3)
N2—N3—C8—C7	0.7 (4)	N5—C17—C18—C19	173.4 (3)
N2—N3—C8—C9	179.6 (3)	C16—C17—C18—C19	−6.7 (5)
C6—C7—C8—N3	−0.5 (4)	C23—C18—C19—C20	−0.8 (5)
C6—C7—C8—C9	−179.2 (3)	C17—C18—C19—C20	−178.6 (3)
N3—C8—C9—C14	5.3 (5)	C18—C19—C20—C21	0.4 (6)
C7—C8—C9—C14	−176.1 (3)	C19—C20—C21—C22	−0.8 (6)
N3—C8—C9—C10	−174.8 (3)	C20—C21—C22—C23	1.6 (6)
C7—C8—C9—C10	3.9 (5)	C21—C22—C23—C18	−2.1 (6)
C14—C9—C10—C11	−1.2 (6)	C19—C18—C23—C22	1.6 (5)
C8—C9—C10—C11	178.9 (4)	C17—C18—C23—C22	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H22···N5ⁱ	0.84 (3)	2.13 (3)	2.878 (4)	148 (4)
O1—H23···N3ⁱⁱ	0.84 (4)	2.20 (2)	2.956 (4)	150 (4)
N2—H17···O1	0.86	2.07	2.918 (4)	167
N4—H5···O1	0.86	2.16	3.007 (4)	170

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₅·H₂O
M_r	381.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.0581 (17), 19.975 (2), 12.451 (2)
β (°)	98.273 (3)
V (Å³)	1983.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.11 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.966, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	9869, 3513, 1796
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.159, 1.05
No. of reflections	3513
No. of parameters	271
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H22···N5ⁱ	0.84 (3)	2.13 (3)	2.878 (4)	148 (4)
O1—H23···N3ⁱⁱ	0.84 (4)	2.20 (2)	2.956 (4)	150 (4)
N2—H17···O1	0.86	2.07	2.918 (4)	167
N4—H5···O1	0.86	2.16	3.007 (4)	170

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

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dias, H. V. R. & Gamage, C. S. P. (2007). Angew. Chem. Int. Ed. 46, 2192–2194. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Zhang, J.-P., Horike, S. & Kitagawa, S. (2007). Angew. Chem. Int. Ed. 46, 889–892. Web of Science CSD CrossRef CAS Google Scholar
Zhou, Y. B. & Chen, W. Z. (2007a). Dalton Trans. pp. 5123-5125. Web of Science CSD CrossRef Google Scholar
Zhou, Y. B. & Chen, W. Z. (2007b). Organometallics, 26, 2742–2746. Web of Science CSD CrossRef CAS 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o820

doi:10.1107/S1600536808008520

Open

access