4-(1,3-Benzothia­zol-2-yl)-N-(2-pyridylmeth­yl)aniline monohydrate

Su, Z.-H.; Wang, Q.-Z.; Teng, L.; Zhang, Y.

doi:10.1107/S1600536808041238

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o86

doi:10.1107/S1600536808041238

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4-(1,3-Benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate

Zhen-Hong Su,^a Qing-Zhi Wang,^a Lei Teng ^b and Yong Zhang ^b ^*

^aMedical School, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^bSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 30 November 2008; accepted 6 December 2008; online 10 December 2008)

In the title compound, C₁₉H₁₅N₃S·H₂O, the benzothiazole ring system forms a dihedral angle of 7.22 (1)° with the benzene ring and the benzene ring forms a dihedral angle of 80.89 (1)° with the pyridine ring. An intramolecular N—H⋯O interaction is present. The crystal structure is stablized by intermolecular O—H⋯N hydrogen bonds, π–π [centroid–centroid distances = 3.782 (1), 3.946 (1) and 3.913 (1) Å] and C—H⋯π interactions, forming a three dimensional-network.

Related literature

For background information, see: Krebs et al. (2005 ); Kung et al. (2001 ); Naiki et al. (1989 ); Qu et al. (2007 ). For the synthetic procedure, see: Stephenson et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₅N₃S·H₂O
M_r = 335.42
Triclinic, $[P \overline 1]$
a = 6.5042 (3) Å
b = 11.5721 (5) Å
c = 11.9415 (5) Å
α = 99.597 (1)°
β = 103.599 (1)°
γ = 99.813 (1)°
V = 840.52 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.961, T_max = 0.980
5408 measured reflections
3243 independent reflections
2342 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.133
S = 0.98
3243 reflections
227 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.856 (10)	2.030 (11)	2.877 (2)	171 (2)
O1—H1B⋯N1ⁱ	0.836 (9)	2.102 (11)	2.929 (2)	170 (3)
O1—H1A⋯N3ⁱⁱ	0.830 (9)	2.069 (10)	2.889 (2)	169 (3)
C18—H18⋯Cgⁱⁱⁱ	0.93	2.82	3.689 (3)	156
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y, z; (iii) x, y, z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041238/lh2740sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041238/lh2740Isup2.hkl

checkCIF report

Comment top

Thioflavin T (ThT) is a benzothiazole dye that exhibits enhanced fluorescence upon binding to amyloid fibrils and is commonly used to diagnose these fibrils (Naiki et al., 1989; Krebs et al., 2005). In an effort to develop in vivo beta-sheet imaging probes, many derivatives of thioflavin T have been synthesized and evaluated (Kung et al., 2001; Qu et al., 2007). As part of our research, the title compound, (I), was prepared and we report the crystal stucture here.

The molecular structure is illustrated in Fig. 1. In (I), the benzothiazole unit is not coplanar with the benzene ring, forming a dihedral angle of 7.22 (1)°. The dihedral angle between the benzene ring and the pyridine ring is 80.89 (1)°. As shown in Fig. 2, molecules are linked into a three-dimensional network by a combination of N—H···O, O—H···N hydrogen bonds, C—H···π (Table 1) and π-π interactions. For the π-π interactions, some related parameters are listed as below: Cg1···Cg1^iv = 3.782 (1) Å, interplanar spacing: 3.680 (1) Å, dihedral angle: 0 °, symmetry code: iv) 1-x,1-y,-z; Cg2···Cg2^v= 3.946 (1) Å, interplanar spacing: 3.678 (1) Å, dihedral angle: 0 °; symmetry code: v) –x,-y,1-z; Cg3···Cg^iv = 3.913 (1) Å, interplanar spacing: 3.748 (1) Å, dihedral angle: 7.1 (1)°. Cg1 is the centroid defined by atoms S1/N1/C1/C6/C7 while Cg2 and Cg3 are the centroids defined by atoms N3/C16—C20 and C1—C6.

Related literature top

For background information, see: Krebs et al. (2005); Kung et al. (2001); Naiki et al. (1989); Qu et al. (2007). For the synthetic procedure, see: Stephenson et al. (2007). [Scheme should show the water molecule]

Experimental top

Compound (I) was synthesized according to the method described by Stephenson et al. (2007). Yellow single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. Part of the crystal structure showing H-bonds as dashed lines.

4-(1,3-Benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate top

Crystal data top

C₁₉H₁₅N₃S·H₂O	Z = 2
M_r = 335.42	F(000) = 352
Triclinic, P1	D_x = 1.325 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5042 (3) Å	Cell parameters from 1809 reflections
b = 11.5721 (5) Å	θ = 1.8–26.0°
c = 11.9415 (5) Å	µ = 0.20 mm⁻¹
α = 99.597 (1)°	T = 298 K
β = 103.599 (1)°	Plate, yellow
γ = 99.813 (1)°	0.20 × 0.10 × 0.10 mm
V = 840.52 (6) Å³

Data collection top

Bruker SMART CCD diffractometer	3243 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −8→8
T_min = 0.961, T_max = 0.980	k = −11→14
5408 measured reflections	l = −14→10

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0653P)²] where P = (F_o² + 2F_c²)/3
3243 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.25 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₅N₃S·H₂O	γ = 99.813 (1)°
M_r = 335.42	V = 840.52 (6) Å³
Triclinic, P1	Z = 2
a = 6.5042 (3) Å	Mo Kα radiation
b = 11.5721 (5) Å	µ = 0.20 mm⁻¹
c = 11.9415 (5) Å	T = 298 K
α = 99.597 (1)°	0.20 × 0.10 × 0.10 mm
β = 103.599 (1)°

Data collection top

Bruker SMART CCD diffractometer	3243 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2342 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.980	R_int = 0.074
5408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	4 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.25 e Å⁻³
3243 reflections	Δρ_min = −0.28 e Å⁻³
227 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 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	0.4402 (3)	0.43406 (18)	−0.20560 (17)	0.0522 (5)
C2	0.5812 (4)	0.4597 (2)	−0.2737 (2)	0.0691 (7)
H2	0.6917	0.4186	−0.2762	0.083*
C3	0.5534 (5)	0.5473 (2)	−0.3374 (2)	0.0801 (8)
H3	0.6479	0.5659	−0.3826	0.096*
C4	0.3900 (5)	0.6079 (2)	−0.3361 (2)	0.0845 (8)
H4	0.3748	0.6659	−0.3810	0.101*
C5	0.2492 (5)	0.5842 (2)	−0.2699 (2)	0.0785 (7)
H5	0.1382	0.6252	−0.2692	0.094*
C6	0.2765 (4)	0.49671 (19)	−0.20326 (18)	0.0580 (6)
C7	0.2929 (3)	0.34399 (17)	−0.08419 (16)	0.0464 (5)
C8	0.2525 (3)	0.26241 (17)	−0.00708 (16)	0.0463 (5)
C9	0.3952 (3)	0.18903 (19)	0.02435 (17)	0.0517 (5)
H9	0.5194	0.1946	−0.0020	0.062*
C10	0.3564 (3)	0.10838 (19)	0.09370 (17)	0.0532 (5)
H10	0.4541	0.0600	0.1128	0.064*
C11	0.1720 (3)	0.09818 (18)	0.13580 (17)	0.0492 (5)
C12	0.0305 (3)	0.17363 (18)	0.10587 (18)	0.0529 (5)
H12	−0.0918	0.1701	0.1339	0.064*
C13	0.0701 (3)	0.25266 (19)	0.03563 (18)	0.0528 (5)
H13	−0.0275	0.3010	0.0160	0.063*
C15	−0.0523 (3)	−0.00822 (19)	0.24393 (18)	0.0552 (5)
H15A	−0.0695	−0.0890	0.2582	0.066*
H15B	−0.1768	−0.0071	0.1811	0.066*
C16	−0.0534 (3)	0.07696 (18)	0.35445 (16)	0.0479 (5)
C17	0.1128 (4)	0.1740 (2)	0.41260 (19)	0.0659 (6)
H17	0.2336	0.1912	0.3844	0.079*
C18	0.0975 (5)	0.2455 (2)	0.5135 (2)	0.0775 (7)
H18	0.2085	0.3115	0.5542	0.093*
C19	−0.0808 (5)	0.2189 (2)	0.5533 (2)	0.0765 (7)
H19	−0.0941	0.2657	0.6214	0.092*
C20	−0.2392 (4)	0.1217 (2)	0.4904 (2)	0.0727 (7)
H20	−0.3609	0.1032	0.5176	0.087*
N1	0.4450 (3)	0.34715 (15)	−0.13801 (15)	0.0531 (4)
N2	0.1390 (3)	0.01759 (17)	0.20410 (16)	0.0592 (5)
H2A	0.228 (3)	−0.0288 (16)	0.2148 (19)	0.069 (7)*
N3	−0.2300 (3)	0.05079 (16)	0.39105 (15)	0.0590 (5)
O1	0.4135 (2)	−0.14685 (15)	0.26027 (16)	0.0699 (5)
H1A	0.526 (3)	−0.0972 (19)	0.299 (2)	0.105*
H1B	0.450 (4)	−0.2003 (18)	0.218 (2)	0.105*
S1	0.12798 (10)	0.44713 (5)	−0.11189 (5)	0.0648 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0604 (12)	0.0473 (12)	0.0409 (11)	0.0022 (10)	0.0057 (10)	0.0090 (9)
C2	0.0644 (14)	0.0747 (17)	0.0662 (15)	0.0035 (12)	0.0152 (12)	0.0250 (13)
C3	0.0883 (18)	0.0772 (18)	0.0708 (16)	−0.0063 (16)	0.0207 (14)	0.0314 (14)
C4	0.118 (2)	0.0620 (16)	0.0721 (17)	0.0093 (16)	0.0193 (17)	0.0320 (14)
C5	0.111 (2)	0.0603 (16)	0.0683 (16)	0.0275 (14)	0.0192 (15)	0.0222 (13)
C6	0.0778 (14)	0.0480 (12)	0.0430 (11)	0.0124 (11)	0.0102 (10)	0.0059 (10)
C7	0.0538 (11)	0.0440 (11)	0.0377 (10)	0.0095 (9)	0.0104 (9)	0.0024 (8)
C8	0.0536 (11)	0.0447 (11)	0.0393 (10)	0.0115 (9)	0.0126 (9)	0.0049 (9)
C9	0.0516 (11)	0.0609 (13)	0.0463 (11)	0.0149 (10)	0.0177 (9)	0.0129 (10)
C10	0.0599 (12)	0.0596 (13)	0.0478 (12)	0.0242 (10)	0.0183 (10)	0.0154 (10)
C11	0.0603 (12)	0.0486 (12)	0.0399 (10)	0.0139 (10)	0.0165 (9)	0.0069 (9)
C12	0.0582 (12)	0.0539 (13)	0.0538 (12)	0.0182 (10)	0.0253 (10)	0.0106 (10)
C13	0.0606 (12)	0.0497 (12)	0.0528 (12)	0.0207 (10)	0.0192 (10)	0.0098 (10)
C15	0.0672 (13)	0.0500 (12)	0.0495 (12)	0.0096 (10)	0.0204 (10)	0.0104 (10)
C16	0.0602 (12)	0.0452 (12)	0.0395 (10)	0.0091 (10)	0.0133 (9)	0.0149 (9)
C17	0.0731 (15)	0.0648 (15)	0.0502 (13)	−0.0061 (12)	0.0172 (11)	0.0067 (11)
C18	0.0994 (19)	0.0625 (16)	0.0526 (14)	−0.0088 (14)	0.0143 (14)	−0.0003 (12)
C19	0.120 (2)	0.0629 (16)	0.0481 (14)	0.0175 (16)	0.0324 (15)	0.0041 (12)
C20	0.0930 (18)	0.0738 (17)	0.0644 (15)	0.0196 (14)	0.0441 (14)	0.0167 (13)
N1	0.0573 (10)	0.0527 (10)	0.0500 (10)	0.0111 (8)	0.0145 (8)	0.0145 (8)
N2	0.0734 (12)	0.0598 (12)	0.0590 (11)	0.0262 (10)	0.0310 (10)	0.0225 (10)
N3	0.0709 (12)	0.0540 (11)	0.0558 (11)	0.0069 (9)	0.0288 (9)	0.0125 (9)
O1	0.0666 (10)	0.0648 (11)	0.0849 (12)	0.0193 (8)	0.0325 (9)	0.0125 (9)
S1	0.0899 (5)	0.0624 (4)	0.0565 (4)	0.0371 (3)	0.0298 (3)	0.0170 (3)

Geometric parameters (Å, º) top

C1—C2	1.389 (3)	C11—C12	1.400 (3)
C1—C6	1.390 (3)	C12—C13	1.372 (3)
C1—N1	1.390 (3)	C12—H12	0.9300
C2—C3	1.376 (3)	C13—H13	0.9300
C2—H2	0.9300	C15—N2	1.436 (3)
C3—C4	1.371 (4)	C15—C16	1.512 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.366 (4)	C15—H15B	0.9700
C4—H4	0.9300	C16—N3	1.328 (2)
C5—C6	1.398 (3)	C16—C17	1.373 (3)
C5—H5	0.9300	C17—C18	1.378 (3)
C6—S1	1.723 (2)	C17—H17	0.9300
C7—N1	1.299 (3)	C18—C19	1.361 (4)
C7—C8	1.458 (3)	C18—H18	0.9300
C7—S1	1.757 (2)	C19—C20	1.360 (3)
C8—C9	1.391 (3)	C19—H19	0.9300
C8—C13	1.392 (3)	C20—N3	1.345 (3)
C9—C10	1.377 (3)	C20—H20	0.9300
C9—H9	0.9300	N2—O1	2.877 (2)
C10—C11	1.400 (3)	N2—H2A	0.856 (10)
C10—H10	0.9300	O1—H1A	0.830 (9)
C11—N2	1.360 (3)	O1—H1B	0.836 (9)

C2—C1—C6	119.7 (2)	C12—C13—C8	121.7 (2)
C2—C1—N1	125.2 (2)	C12—C13—H13	119.1
C6—C1—N1	115.02 (19)	C8—C13—H13	119.1
C3—C2—C1	118.4 (2)	N2—C15—C16	115.24 (17)
C3—C2—H2	120.8	N2—C15—H15A	108.5
C1—C2—H2	120.8	C16—C15—H15A	108.5
C4—C3—C2	121.8 (3)	N2—C15—H15B	108.5
C4—C3—H3	119.1	C16—C15—H15B	108.5
C2—C3—H3	119.1	H15A—C15—H15B	107.5
C5—C4—C3	120.9 (3)	N3—C16—C17	122.3 (2)
C5—C4—H4	119.5	N3—C16—C15	114.46 (18)
C3—C4—H4	119.5	C17—C16—C15	123.3 (2)
C4—C5—C6	118.2 (3)	C16—C17—C18	118.9 (2)
C4—C5—H5	120.9	C16—C17—H17	120.6
C6—C5—H5	120.9	C18—C17—H17	120.6
C1—C6—C5	121.0 (2)	C19—C18—C17	119.6 (2)
C1—C6—S1	109.75 (17)	C19—C18—H18	120.2
C5—C6—S1	129.3 (2)	C17—C18—H18	120.2
N1—C7—C8	124.97 (18)	C20—C19—C18	118.0 (2)
N1—C7—S1	114.73 (15)	C20—C19—H19	121.0
C8—C7—S1	120.30 (15)	C18—C19—H19	121.0
C9—C8—C13	117.53 (19)	N3—C20—C19	123.8 (2)
C9—C8—C7	120.40 (18)	N3—C20—H20	118.1
C13—C8—C7	122.05 (19)	C19—C20—H20	118.1
C10—C9—C8	121.39 (19)	C7—N1—C1	111.11 (18)
C10—C9—H9	119.3	C11—N2—C15	124.34 (19)
C8—C9—H9	119.3	C11—N2—O1	124.36 (14)
C9—C10—C11	120.9 (2)	C15—N2—O1	110.78 (13)
C9—C10—H10	119.5	C11—N2—H2A	117.8 (16)
C11—C10—H10	119.5	C15—N2—H2A	117.1 (16)
N2—C11—C12	123.07 (19)	C16—N3—C20	117.4 (2)
N2—C11—C10	119.30 (19)	N2—O1—H1A	99 (2)
C12—C11—C10	117.63 (19)	N2—O1—H1B	132 (2)
C13—C12—C11	120.76 (19)	H1A—O1—H1B	107.1 (15)
C13—C12—H12	119.6	C6—S1—C7	89.37 (10)
C11—C12—H12	119.6

C6—C1—C2—C3	0.0 (3)	N2—C15—C16—N3	−179.05 (18)
N1—C1—C2—C3	179.0 (2)	N2—C15—C16—C17	1.3 (3)
C1—C2—C3—C4	−0.8 (4)	N3—C16—C17—C18	1.1 (4)
C2—C3—C4—C5	0.8 (4)	C15—C16—C17—C18	−179.2 (2)
C3—C4—C5—C6	0.1 (4)	C16—C17—C18—C19	−0.1 (4)
C2—C1—C6—C5	0.9 (3)	C17—C18—C19—C20	−0.3 (4)
N1—C1—C6—C5	−178.17 (19)	C18—C19—C20—N3	−0.3 (4)
C2—C1—C6—S1	−179.81 (16)	C8—C7—N1—C1	179.53 (17)
N1—C1—C6—S1	1.1 (2)	S1—C7—N1—C1	0.3 (2)
C4—C5—C6—C1	−1.0 (3)	C2—C1—N1—C7	−179.93 (18)
C4—C5—C6—S1	179.93 (19)	C6—C1—N1—C7	−0.9 (2)
N1—C7—C8—C9	7.2 (3)	C12—C11—N2—C15	6.3 (3)
S1—C7—C8—C9	−173.62 (15)	C10—C11—N2—C15	−174.45 (18)
N1—C7—C8—C13	−171.42 (18)	C12—C11—N2—O1	177.22 (15)
S1—C7—C8—C13	7.8 (3)	C10—C11—N2—O1	−3.5 (3)
C13—C8—C9—C10	0.9 (3)	C16—C15—N2—C11	−84.0 (3)
C7—C8—C9—C10	−177.73 (18)	C16—C15—N2—O1	104.04 (17)
C8—C9—C10—C11	−0.5 (3)	C17—C16—N3—C20	−1.7 (3)
C9—C10—C11—N2	−179.97 (19)	C15—C16—N3—C20	178.7 (2)
C9—C10—C11—C12	−0.7 (3)	C19—C20—N3—C16	1.3 (4)
N2—C11—C12—C13	−179.35 (19)	C1—C6—S1—C7	−0.75 (15)
C10—C11—C12—C13	1.4 (3)	C5—C6—S1—C7	178.4 (2)
C11—C12—C13—C8	−1.0 (3)	N1—C7—S1—C6	0.28 (16)
C9—C8—C13—C12	−0.2 (3)	C8—C7—S1—C6	−179.01 (16)
C7—C8—C13—C12	178.42 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86 (1)	2.03 (1)	2.877 (2)	171 (2)
O1—H1B···N1ⁱ	0.84 (1)	2.10 (1)	2.929 (2)	170 (3)
O1—H1A···N3ⁱⁱ	0.83 (1)	2.07 (1)	2.889 (2)	169 (3)
C18—H18···Cgⁱⁱⁱ	0.93	2.82	3.689 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃S·H₂O
M_r	335.42
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.5042 (3), 11.5721 (5), 11.9415 (5)
α, β, γ (°)	99.597 (1), 103.599 (1), 99.813 (1)
V (Å³)	840.52 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.961, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5408, 3243, 2342
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.133, 0.98
No. of reflections	3243
No. of parameters	227
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.856 (10)	2.030 (11)	2.877 (2)	171 (2)
O1—H1B···N1ⁱ	0.836 (9)	2.102 (11)	2.929 (2)	170 (3)
O1—H1A···N3ⁱⁱ	0.830 (9)	2.069 (10)	2.889 (2)	169 (3)
C18—H18···Cgⁱⁱⁱ	0.93	2.82	3.689 (3)	156

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

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stephenson, K. A., Chandra, R., Zhuang, Z.-P., Hou, C., Oya, S., Kung, M.-P. & Kung, H. F. (2007). Bioconjugate Chem. 18, 238–246. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 1| January 2009| Page o86

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