2,2′-[1-(2,4,6-Trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol

Li, Z.-S.; Li, X.-B.; Sun, B.-W.

doi:10.1107/S1600536808001505

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o491

doi:10.1107/S1600536808001505

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2,2′-[1-(2,4,6-Trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol

Zhong-Shu Li,^a Xiu-Bing Li ^b and Bai-Wang Sun ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bDepartment of Chemistry, Key Laboratory of Medicinal Chemistry for Natural Resources of the Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 27 December 2007; accepted 15 January 2008; online 23 January 2008)

The title compound, C₂₀H₁₂Cl₃N₃O₂, was synthesized by the reaction of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one with 2,4,6-trichlorophenylhydrazine in ethanol. The trichlorophenyl ring is nearly perpendicular to the triazole plane [dihedral angle 80.56 (8)°], whereas the two hydroxyphenyl rings are approximately coplanar with the triazole ring [dihedral angles of 2.79 (12) and 8.00 (14)°]. Intramolecular O—H⋯N hydrogen bonding is observed between the hydroxyphenyl and triazole rings.

Related literature

For general background, see: Nisbet-Brown et al. (2003 ); Steinhauser et al. (2004 ).

Experimental

Crystal data

C₂₀H₁₂Cl₃N₃O₂
M_r = 432.68
Monoclinic, P 2₁ /c
a = 14.328 (3) Å
b = 12.021 (2) Å
c = 12.014 (2) Å
β = 104.99 (3)°
V = 1998.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.907, T_max = 0.915
16254 measured reflections
3501 independent reflections
3052 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.104
S = 1.11
3501 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N3	0.83 (3)	1.89 (3)	2.640 (3)	149 (3)
O2—H2A⋯N2	0.81 (2)	1.94 (2)	2.648 (3)	146 (3)

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001505/xu2398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001505/xu2398Isup2.hkl

checkCIF report

Comment top

3,5-Bis(2-hydroxyphenyl)-1-phenyl-1,2,4-triazole core has been successfully used a motif for the development of biologically interesting molecules, including active iron chelator (Nisbet-Brown et al., 2003; Steinhauser et al., 2004). We report here the crystal structure of the title triazole compound.

In the title molecule (Fig. 1), 3-(2-hydroxyphenyl) is almost co-planar with 1,2,4-triazole ring, dihedral angle being 2.79 (12)°. The 5-(2-hydroxyphenyl) ring forms a dihedral angle of 9.70 (13)° with triazole plane. The trichlorophenyl is nearly perpendicular to the triazole plane with a dihedral angle of 80.56 (8)°. Intra-molecular N—H···O hydrogen bonding is observed between hydroxyphenyl and triazole rings (Table 1).

Related literature top

For general background, see: Nisbet-Brown et al. (2003); Steinhauser et al. (2004).

Experimental top

2-(2-Hydroxyphenyl)benz[e][1,3]oxazin-4-one (2.4 g) was mixed with 2,4,6-trichlorophenylhydrazine (2.2 g) in ethanol (30 ml). The mixture was refluxed for 3 h, after cooling to room temperature, the mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The title compound was crystallized from methanol. The colourless crystals were obtained by slow evaporation of methanol.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005; data reduction: CrystalClear (Rigaku, 2005; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2,2'-[1-(2,4,6-Trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol top

Crystal data top

C₂₀H₁₂Cl₃N₃O₂	F(000) = 880
M_r = 432.68	D_x = 1.438 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5847 reflections
a = 14.328 (3) Å	θ = 3.0–28.4°
b = 12.021 (2) Å	µ = 0.48 mm⁻¹
c = 12.014 (2) Å	T = 293 K
β = 104.99 (3)°	Block, colourless
V = 1998.7 (7) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	3501 independent reflections
Radiation source: fine-focus sealed tube	3052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.907, T_max = 0.915	l = −14→14
16254 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.034P)² + 0.892P] where P = (F_o² + 2F_c²)/3
3501 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₂Cl₃N₃O₂	V = 1998.7 (7) Å³
M_r = 432.68	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.328 (3) Å	µ = 0.48 mm⁻¹
b = 12.021 (2) Å	T = 293 K
c = 12.014 (2) Å	0.20 × 0.20 × 0.18 mm
β = 104.99 (3)°

Data collection top

Rigaku SCXmini diffractometer	3501 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3052 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.915	R_int = 0.047
16254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.36 e Å⁻³
3501 reflections	Δρ_min = −0.35 e Å⁻³
261 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
Cl1	0.25005 (6)	−0.25222 (6)	0.53114 (7)	0.0819 (3)
Cl2	0.36388 (5)	0.15110 (5)	0.40863 (6)	0.0679 (2)
Cl3	0.49510 (6)	−0.22786 (7)	0.25494 (7)	0.0814 (2)
N1	0.25668 (12)	−0.00229 (15)	0.52989 (14)	0.0448 (4)
N2	0.29844 (12)	0.00432 (15)	0.64746 (14)	0.0452 (4)
N3	0.14978 (11)	0.08336 (15)	0.60312 (14)	0.0437 (4)
C1	0.33274 (16)	0.04839 (17)	0.89318 (18)	0.0460 (5)
C2	0.34437 (19)	0.0687 (2)	1.0104 (2)	0.0625 (6)
H2C	0.4018	0.0490	1.0632	0.075*
C3	0.2707 (2)	0.1181 (2)	1.0485 (2)	0.0678 (7)
H3B	0.2788	0.1305	1.1268	0.081*
C4	0.1850 (2)	0.1491 (2)	0.9706 (2)	0.0638 (7)
H4A	0.1360	0.1823	0.9967	0.077*
C5	0.17289 (17)	0.13019 (19)	0.8534 (2)	0.0531 (6)
H5A	0.1155	0.1513	0.8014	0.064*
C6	0.24623 (14)	0.07958 (17)	0.81220 (17)	0.0410 (5)
C7	0.23151 (14)	0.05618 (16)	0.68776 (17)	0.0399 (4)
C8	0.16669 (14)	0.04599 (17)	0.50442 (18)	0.0422 (5)
C9	0.09851 (15)	0.06060 (19)	0.38957 (18)	0.0483 (5)
C10	0.01411 (16)	0.1254 (2)	0.3802 (2)	0.0555 (6)
C11	−0.04752 (19)	0.1462 (2)	0.2709 (3)	0.0749 (8)
H11A	−0.1024	0.1895	0.2645	0.090*
C12	−0.0282 (2)	0.1036 (3)	0.1730 (3)	0.0841 (9)
H12A	−0.0691	0.1202	0.1012	0.101*
C13	0.0522 (2)	0.0357 (3)	0.1803 (2)	0.0850 (9)
H13A	0.0637	0.0045	0.1142	0.102*
C14	0.11476 (18)	0.0154 (3)	0.2880 (2)	0.0698 (7)
H14A	0.1687	−0.0292	0.2930	0.084*
C15	0.31228 (14)	−0.05594 (18)	0.46145 (17)	0.0430 (5)
C16	0.36702 (15)	0.00659 (18)	0.40185 (17)	0.0454 (5)
C17	0.42321 (16)	−0.0452 (2)	0.33763 (19)	0.0524 (6)
H17A	0.4587	−0.0035	0.2978	0.063*
C18	0.42469 (17)	−0.1615 (2)	0.3349 (2)	0.0550 (6)
C19	0.37295 (18)	−0.2260 (2)	0.3944 (2)	0.0609 (6)
H19A	0.3758	−0.3033	0.3923	0.073*
C20	0.31687 (16)	−0.1727 (2)	0.4570 (2)	0.0520 (5)
O1	−0.01130 (13)	0.16967 (17)	0.47345 (18)	0.0718 (5)
H1A	0.032 (2)	0.156 (3)	0.533 (3)	0.087 (10)*
O2	0.40802 (12)	−0.00300 (15)	0.86177 (16)	0.0593 (4)
H2A	0.3949 (19)	−0.013 (2)	0.793 (2)	0.064 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0879 (5)	0.0692 (5)	0.1039 (6)	−0.0208 (4)	0.0528 (5)	−0.0016 (4)
Cl2	0.0863 (5)	0.0487 (3)	0.0809 (5)	0.0037 (3)	0.0437 (4)	0.0037 (3)
Cl3	0.0916 (5)	0.0814 (5)	0.0878 (5)	0.0185 (4)	0.0529 (4)	−0.0117 (4)
N1	0.0394 (9)	0.0578 (11)	0.0380 (9)	0.0044 (8)	0.0116 (7)	−0.0019 (8)
N2	0.0411 (9)	0.0563 (11)	0.0381 (9)	0.0046 (8)	0.0100 (7)	−0.0020 (8)
N3	0.0368 (9)	0.0510 (10)	0.0449 (10)	0.0025 (7)	0.0136 (8)	0.0033 (8)
C1	0.0516 (12)	0.0416 (11)	0.0455 (12)	0.0003 (9)	0.0140 (10)	0.0031 (9)
C2	0.0686 (16)	0.0713 (16)	0.0440 (13)	0.0056 (13)	0.0083 (11)	0.0029 (11)
C3	0.091 (2)	0.0722 (17)	0.0421 (14)	0.0006 (15)	0.0210 (13)	−0.0036 (12)
C4	0.0784 (17)	0.0642 (16)	0.0581 (16)	0.0057 (13)	0.0345 (14)	−0.0086 (12)
C5	0.0543 (13)	0.0559 (14)	0.0511 (13)	0.0070 (11)	0.0176 (11)	−0.0018 (10)
C6	0.0460 (11)	0.0383 (10)	0.0411 (11)	−0.0023 (9)	0.0152 (9)	0.0008 (8)
C7	0.0383 (10)	0.0419 (11)	0.0409 (11)	−0.0005 (8)	0.0130 (9)	0.0016 (8)
C8	0.0358 (10)	0.0487 (12)	0.0438 (12)	−0.0022 (9)	0.0136 (9)	0.0033 (9)
C9	0.0389 (11)	0.0603 (14)	0.0441 (12)	−0.0057 (10)	0.0079 (9)	0.0071 (10)
C10	0.0417 (12)	0.0601 (14)	0.0614 (15)	−0.0054 (10)	0.0075 (11)	0.0078 (11)
C11	0.0527 (15)	0.0833 (19)	0.075 (2)	0.0037 (14)	−0.0075 (14)	0.0187 (15)
C12	0.0689 (19)	0.114 (3)	0.0552 (17)	−0.0103 (17)	−0.0095 (14)	0.0228 (16)
C13	0.0680 (18)	0.136 (3)	0.0463 (16)	−0.0049 (18)	0.0067 (13)	−0.0005 (16)
C14	0.0504 (14)	0.110 (2)	0.0458 (14)	0.0045 (14)	0.0061 (11)	−0.0033 (14)
C15	0.0380 (10)	0.0542 (13)	0.0371 (11)	0.0028 (9)	0.0102 (9)	−0.0043 (9)
C16	0.0453 (12)	0.0498 (12)	0.0418 (11)	0.0031 (9)	0.0124 (9)	0.0005 (9)
C17	0.0521 (13)	0.0618 (15)	0.0476 (13)	0.0048 (11)	0.0210 (10)	0.0042 (10)
C18	0.0550 (13)	0.0635 (15)	0.0506 (13)	0.0096 (11)	0.0210 (11)	−0.0079 (11)
C19	0.0673 (16)	0.0496 (13)	0.0704 (17)	0.0009 (11)	0.0262 (13)	−0.0083 (11)
C20	0.0499 (12)	0.0550 (14)	0.0537 (13)	−0.0060 (10)	0.0180 (10)	−0.0029 (10)
O1	0.0472 (10)	0.0926 (14)	0.0714 (13)	0.0185 (9)	0.0078 (9)	−0.0004 (10)
O2	0.0530 (10)	0.0742 (12)	0.0491 (10)	0.0160 (8)	0.0103 (8)	0.0052 (9)

Geometric parameters (Å, º) top

Cl1—C20	1.751 (2)	C9—C14	1.410 (3)
Cl2—C16	1.740 (2)	C9—C10	1.419 (3)
Cl3—C18	1.754 (2)	C10—O1	1.371 (3)
N1—C8	1.374 (3)	C10—C11	1.402 (4)
N1—N2	1.386 (2)	C11—C12	1.375 (4)
N1—C15	1.437 (2)	C11—H11A	0.9300
N2—C7	1.335 (3)	C12—C13	1.395 (4)
N3—C8	1.347 (3)	C12—H12A	0.9300
N3—C7	1.377 (3)	C13—C14	1.392 (4)
C1—O2	1.378 (3)	C13—H13A	0.9300
C1—C2	1.396 (3)	C14—H14A	0.9300
C1—C6	1.414 (3)	C15—C20	1.406 (3)
C2—C3	1.388 (4)	C15—C16	1.408 (3)
C2—H2C	0.9300	C16—C17	1.397 (3)
C3—C4	1.387 (4)	C17—C18	1.399 (3)
C3—H3B	0.9300	C17—H17A	0.9300
C4—C5	1.393 (3)	C18—C19	1.391 (3)
C4—H4A	0.9300	C19—C20	1.391 (3)
C5—C6	1.410 (3)	C19—H19A	0.9300
C5—H5A	0.9300	O1—H1A	0.83 (3)
C6—C7	1.482 (3)	O2—H2A	0.80 (3)
C8—C9	1.480 (3)

C8—N1—N2	109.60 (16)	C11—C10—C9	119.3 (2)
C8—N1—C15	133.55 (17)	C12—C11—C10	121.2 (3)
N2—N1—C15	116.84 (15)	C12—C11—H11A	119.4
C7—N2—N1	103.59 (15)	C10—C11—H11A	119.4
C8—N3—C7	104.99 (16)	C11—C12—C13	120.6 (3)
O2—C1—C2	117.2 (2)	C11—C12—H12A	119.7
O2—C1—C6	122.65 (19)	C13—C12—H12A	119.7
C2—C1—C6	120.2 (2)	C14—C13—C12	118.9 (3)
C3—C2—C1	120.3 (2)	C14—C13—H13A	120.5
C3—C2—H2C	119.9	C12—C13—H13A	120.5
C1—C2—H2C	119.9	C13—C14—C9	121.8 (3)
C4—C3—C2	120.6 (2)	C13—C14—H14A	119.1
C4—C3—H3B	119.7	C9—C14—H14A	119.1
C2—C3—H3B	119.7	C20—C15—C16	118.40 (19)
C3—C4—C5	119.7 (2)	C20—C15—N1	120.51 (19)
C3—C4—H4A	120.2	C16—C15—N1	121.03 (19)
C5—C4—H4A	120.2	C17—C16—C15	121.3 (2)
C4—C5—C6	121.0 (2)	C17—C16—Cl2	119.75 (17)
C4—C5—H5A	119.5	C15—C16—Cl2	118.97 (16)
C6—C5—H5A	119.5	C16—C17—C18	118.2 (2)
C5—C6—C1	118.25 (19)	C16—C17—H17A	120.9
C5—C6—C7	120.75 (19)	C18—C17—H17A	120.9
C1—C6—C7	120.97 (18)	C19—C18—C17	122.1 (2)
N2—C7—N3	113.35 (17)	C19—C18—Cl3	119.10 (19)
N2—C7—C6	121.76 (18)	C17—C18—Cl3	118.77 (18)
N3—C7—C6	124.89 (17)	C18—C19—C20	118.7 (2)
N3—C8—N1	108.46 (17)	C18—C19—H19A	120.7
N3—C8—C9	123.73 (18)	C20—C19—H19A	120.7
N1—C8—C9	127.77 (19)	C19—C20—C15	121.3 (2)
C14—C9—C10	118.1 (2)	C19—C20—Cl1	119.44 (19)
C14—C9—C8	123.0 (2)	C15—C20—Cl1	119.25 (17)
C10—C9—C8	118.8 (2)	C10—O1—H1A	109 (2)
O1—C10—C11	117.4 (2)	C1—O2—H2A	110.6 (19)
O1—C10—C9	123.3 (2)

C8—N1—N2—C7	0.1 (2)	C14—C9—C10—O1	177.2 (2)
C15—N1—N2—C7	−179.52 (17)	C8—C9—C10—O1	−4.5 (3)
O2—C1—C2—C3	−178.7 (2)	C14—C9—C10—C11	−2.7 (3)
C6—C1—C2—C3	0.9 (4)	C8—C9—C10—C11	175.6 (2)
C1—C2—C3—C4	−0.8 (4)	O1—C10—C11—C12	−179.0 (3)
C2—C3—C4—C5	0.2 (4)	C9—C10—C11—C12	0.9 (4)
C3—C4—C5—C6	0.2 (4)	C10—C11—C12—C13	1.9 (5)
C4—C5—C6—C1	0.0 (3)	C11—C12—C13—C14	−2.6 (5)
C4—C5—C6—C7	177.9 (2)	C12—C13—C14—C9	0.7 (5)
O2—C1—C6—C5	179.0 (2)	C10—C9—C14—C13	2.0 (4)
C2—C1—C6—C5	−0.6 (3)	C8—C9—C14—C13	−176.3 (3)
O2—C1—C6—C7	1.1 (3)	C8—N1—C15—C20	−100.5 (3)
C2—C1—C6—C7	−178.4 (2)	N2—N1—C15—C20	79.1 (2)
N1—N2—C7—N3	−0.2 (2)	C8—N1—C15—C16	82.6 (3)
N1—N2—C7—C6	179.23 (17)	N2—N1—C15—C16	−97.8 (2)
C8—N3—C7—N2	0.2 (2)	C20—C15—C16—C17	1.3 (3)
C8—N3—C7—C6	−179.23 (18)	N1—C15—C16—C17	178.30 (19)
C5—C6—C7—N2	−177.3 (2)	C20—C15—C16—Cl2	−178.83 (16)
C1—C6—C7—N2	0.6 (3)	N1—C15—C16—Cl2	−1.8 (3)
C5—C6—C7—N3	2.1 (3)	C15—C16—C17—C18	−0.7 (3)
C1—C6—C7—N3	179.90 (19)	Cl2—C16—C17—C18	179.45 (17)
C7—N3—C8—N1	−0.1 (2)	C16—C17—C18—C19	−0.5 (4)
C7—N3—C8—C9	−178.01 (19)	C16—C17—C18—Cl3	−179.86 (17)
N2—N1—C8—N3	0.0 (2)	C17—C18—C19—C20	1.0 (4)
C15—N1—C8—N3	179.5 (2)	Cl3—C18—C19—C20	−179.63 (19)
N2—N1—C8—C9	177.80 (19)	C18—C19—C20—C15	−0.3 (4)
C15—N1—C8—C9	−2.6 (4)	C18—C19—C20—Cl1	179.26 (19)
N3—C8—C9—C14	−176.2 (2)	C16—C15—C20—C19	−0.8 (3)
N1—C8—C9—C14	6.3 (4)	N1—C15—C20—C19	−177.8 (2)
N3—C8—C9—C10	5.6 (3)	C16—C15—C20—Cl1	179.62 (16)
N1—C8—C9—C10	−172.0 (2)	N1—C15—C20—Cl1	2.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	0.83 (3)	1.89 (3)	2.640 (3)	149 (3)
O2—H2A···N2	0.81 (2)	1.94 (2)	2.648 (3)	146 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂Cl₃N₃O₂
M_r	432.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.328 (3), 12.021 (2), 12.014 (2)
β (°)	104.99 (3)
V (Å³)	1998.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.907, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	16254, 3501, 3052
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.11
No. of reflections	3501
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: CrystalClear (Rigaku, 2005), CrystalClear (Rigaku, 2005, SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	0.83 (3)	1.89 (3)	2.640 (3)	149 (3)
O2—H2A···N2	0.81 (2)	1.94 (2)	2.648 (3)	146 (3)

References

Nisbet-Brown, E., Olivieri, N. F., Giardina, P. J., Grady, R. W., Neufeld, E. J., Sechaud, R., Krebs-Brown, A. J., Anderson, J. R., Alberti, D., Sizer, K. C. & Nathan, D. G. (2003). Lancet, 361, 1597–1602. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steinhauser, S., Heinz, U., Bartholomä, M., Weyhermüller, T., Nick, H. & Hegetschweiler, K. (2004). Eur. J. Inorg. Chem. pp. 4177–4192. Web of Science CSD CrossRef Google Scholar

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Volume 64| Part 2| February 2008| Page o491

doi:10.1107/S1600536808001505

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