trans-4-(2-Amino-5-bromo-6-methyl­pyrimidin-4-ylamino)-1-methyl­cyclo­hexa­nol

Hoffman, J.E.; Cheng, H.; Rheingold, A.L.; DiPasquale, A.; Yanovsky, A.

doi:10.1107/S1600536809035533

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2374

doi:10.1107/S1600536809035533

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trans-4-(2-Amino-5-bromo-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol

Jacqui E. Hoffman,^a Henry Cheng,^a Arnold L. Rheingold,^b Antonio DiPasquale ^b and Alex Yanovsky ^a ^*

^aPfizer Global Research and Development, La Jolla Labs, 10770 Science Center Drive, San Diego, CA 92121, USA, and ^bDepartment of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: alex.yanovsky@pfizer.com

(Received 13 August 2009; accepted 2 September 2009; online 9 September 2009)

The title compound, C₁₂H₁₉BrN₄O, represents the minor component of the two products obtained in a series of transformations involving the Grignard reaction of tert-butoxycarbonyl-protected 4-aminocyclohexanone with MeMgBr, and subsequent interaction of the obtained amino-substituted cyclohexanol with 4-chloro-6-methylpyrimidin-2-amine followed by bromination with N-bromosuccinimide. The X-ray structure showed that this product represents a trans isomer with respect to the amino and hydroxy substituents in the cyclohexyl ring; the dihedral angle between the aminopyrimidine plane and the (noncrystallographic) mirror plane of the substituted cyclohexyl fragment is 33.6 (3)°. Only two of the four potentially `active' H atoms participate in intermolecular N—H⋯O and O—H⋯N hydrogen bonds, linking the molecules into layers parallel to the (10 $[\overline{1}]$ ) plane.

Related literature

For the structure of a similar N-pyrimidine derivative of aminocyclohexane, see Melguizo et al. (2003 ).

Experimental

Crystal data

C₁₂H₁₉BrN₄O
M_r = 315.22
Monoclinic, P 2₁ /n
a = 9.9514 (18) Å
b = 7.1879 (11) Å
c = 19.566 (4) Å
β = 91.053 (3)°
V = 1399.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 198 K
0.10 × 0.10 × 0.08 mm

Data collection

Siemens P4 with APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.758, T_max = 0.799
8853 measured reflections
3251 independent reflections
2500 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.05
3251 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.88	2.03	2.828 (3)	151
O1—H1⋯N1ⁱⁱ	0.84	2.02	2.803 (3)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-32 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035533/bg2293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035533/bg2293Isup2.hkl

checkCIF report

Comment top

The Grignard reaction of tert-butoxycarbonyl(BOC)-protected 4-aminocyclohexanone, 4-C₄H₉OC(O)N(H)C₆H₉O, with MeMgBr produced the mixture of cis- and trans- 4-BOC-amino-1-methyl-cyclohexanols, which was subsequently reacted with 4-chloro-6-methylpyrimidin-2-amine and then brominated with N-bromosuccinimide. The isomeric mixture of the products was separated by means of flash chromatography and the corresponding X-ray structural study of the minor isomer showed that the title compound represents a trans-isomer with respect to the amino and hydroxy substituents in the cyclohexane ring (Fig. 1). The plane of the diaminopyrimidine C1/C2/C3/C4/N1/N2/N4 fragment forms a dihedral angle of 33.6 (3)° with the approximate mirror plane of the cyclohexyl fragment, namely the plane passing through N4/C6/C9/C12/O1. This conformation is significantly different from that observed in the related compound described in Melguizo et al., 2003, where the dihedral angle formed by the aminopyrimidine plane and the mirror plane of the cyclohexyl ring is just 13.6°.

There are four H atoms in the molecule, which are capable of H-bond formation. However, only two of them (H1 and H3A) participate in intermolecular H-bonds (Table 1), which link the molecules into layers parallel to the (1,0,-1) plane of the crystal (Fig. 2).

Related literature top

For the structure of a similar N-pyrimidine derivative of aminocyclohexane, see Melguizo et al. (2003).

Experimental top

Synthesis of tert-butyl 4-hydroxy-4-methylcyclohexylcarbamate. To a cooled (0°C) solution of 4-N-boc-amino-cyclohexanone (4.79 g, 22.5 mmol) in tetrahydrofuran (190 ml) was added methylmagnesium bromide (3 M solution in diethyl ether, 22.5 ml, 67.2 mmol). The ice bath was removed and the reaction was stirred at room temperature for 6 h, and then quenched with saturated ammonia chloride and water. The reaction mixture was concentrated and residue was dissolved in ethyl acetate and washed with saturated ammonia chloride, dried (MgSO4), filtered, and concentrated again. The crude product was purified by flash chromatography eluting with hexanes/ethyl acetate (10–50%) then chloroform/methanol (10%) to afford tert-butyl 4-hydroxy-4-methylcyclohexylcarbamate as a mixture of isomers (2.72 g, 53%).

Synthesis of 4-(2-amino-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol. To a cooled (0°C) solution of tert-butyl 4-hydroxy-4-methylcyclohexylcarbamate (2.72 g, 11.9 mmol) in dichloromethane was added hydrochloric acid (2 M solution in diethyl ether, 10 eq). The ice bath was removed and the solution was stirred at room temperature for 6 hrs then concentrated to afford 4-amino-1-methylcyclohexanol hydrochloride, which was used without further purification. A solution of 2-amino-4-chloro-6-methylpyrimidine (2.20 g, 15.4 mmol), 4-amino-1-methylcyclohexanol hydrochloride, and diisopropylethyl amine (7.6 ml, 44 mmol) in dimethyl acetamide (52 ml) was heated to 160°C in a sealed tube overnight. The reaction mixture was concentrated, the solids were slurried in chloroform and the filtrate was concentrated again. The crude product was purified by flash choromatagraphy eluting with chloroform/7 N ammonia in methanol followed by SFC chromatography to afford 4-(2-amino-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol as a mixture of isomers (600 mg, 17% over 2 steps).

Synthesis of 4-(2-amino-5-bromo-6-methylpyrimidin-4-ylamino) -1-methylcyclohexanol. To a solution of 4-(2-amino-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol (600 mg, 2.54 mmol) in dichloromethane (20.0 ml) was added N-bromosuccinimide (452 mg, 2.54 mmol). After stirring for 2.5 hrs at room temperature, the solution was concentrated. The residue was dissolved in ethyl acetate (450 ml) and washed with 50% saturated sodium carbonate, brine, dried (MgSO4), filtered, and concentrated again. The crude product was purified by flash chromatography to afford major (407 mg, 51%) and minor (151 mg, 19%) isomers of 4-(2-amino-5-bromo-6-methylpyrimidin-4-ylamino)-1-methylcyclohexanol. Minor isomer (the title compound) was subjected to the X-ray study and proved to be the trans-isomer.

1H NMR spectra for major (cis) isomer: (400 MHz, DMSO-d6) δp.p.m. 1.11 (s, 3 H) 1.26 - 1.37 (m, 2 H) 1.52 - 1.61 (m, 4 H) 1.61 - 1.73 (m, 2 H) 2.17 (s, 3 H) 3.77 - 3.87 (m, 1 H) 4.06 (s, 1 H) 5.73 (d, J=8.34 Hz, 1 H) 6.08 (s, 2 H)

1H NMR spectra for minor (trans) isomer (the title compound): (400 MHz, DMSO-d6) δp.p.m. 1.16 (s, 3 H) 1.36 - 1.45 (m, 2 H) 1.45 - 1.56 (m, 4 H) 1.64 - 1.73 (m, 2 H) 2.17 (s, 3 H) 3.87 - 3.97 (m, 1 H) 4.28 (s, 1 H) 5.93 (d, J=8.59 Hz, 1 H) 6.11 (s, 2 H)

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing 50% probability displacement ellipsoids and atom numbering scheme; H atoms are drawn as circles with arbitrary small radius.
	Fig. 2. Packing diagram for the title compound viewed approximately along the b axis. H-Bonds are shown as dashed lines; H atoms bound to carbon atoms are omitted.

trans-4-(2-Amino-5-bromo-6-methylpyrimidin-4-ylamino)-1- methylcyclohexanol top

Crystal data top

C₁₂H₁₉BrN₄O	F(000) = 648
M_r = 315.22	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2554 reflections
a = 9.9514 (18) Å	θ = 2.3–26.0°
b = 7.1879 (11) Å	µ = 2.93 mm⁻¹
c = 19.566 (4) Å	T = 198 K
β = 91.053 (3)°	Prism, colorless
V = 1399.3 (4) Å³	0.10 × 0.10 × 0.08 mm
Z = 4

Data collection top

Siemens P4 with APEX CCD area-detector diffractometer	3251 independent reflections
Radiation source: fine-focus sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
T_min = 0.758, T_max = 0.799	k = −9→3
8853 measured reflections	l = −25→25

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0567P)² + 0.5508P] where P = (F_o² + 2F_c²)/3
3251 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

C₁₂H₁₉BrN₄O	V = 1399.3 (4) Å³
M_r = 315.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9514 (18) Å	µ = 2.93 mm⁻¹
b = 7.1879 (11) Å	T = 198 K
c = 19.566 (4) Å	0.10 × 0.10 × 0.08 mm
β = 91.053 (3)°

Data collection top

Siemens P4 with APEX CCD area-detector diffractometer	3251 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2500 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.799	R_int = 0.030
8853 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.83 e Å⁻³
3251 reflections	Δρ_min = −0.77 e Å⁻³
166 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	0.5559 (2)	0.1796 (4)	0.70305 (12)	0.0340 (5)
C2	0.4564 (2)	0.4484 (3)	0.74028 (12)	0.0345 (5)
C3	0.3689 (2)	0.4380 (4)	0.68582 (12)	0.0343 (5)
C4	0.3783 (2)	0.2877 (3)	0.64026 (11)	0.0308 (5)
C5	0.4551 (4)	0.6010 (4)	0.79203 (16)	0.0553 (8)
H5A	0.5224	0.5753	0.8280	0.083*
H5B	0.3659	0.6084	0.8123	0.083*
H5C	0.4760	0.7195	0.7698	0.083*
C6	0.3088 (3)	0.1409 (3)	0.53025 (12)	0.0360 (5)
H6	0.3451	0.0203	0.5480	0.043*
C7	0.4063 (2)	0.2217 (4)	0.47943 (12)	0.0371 (6)
H7A	0.4223	0.1297	0.4428	0.045*
H7B	0.4934	0.2472	0.5029	0.045*
C8	0.3519 (3)	0.4009 (4)	0.44790 (13)	0.0387 (6)
H8A	0.4163	0.4467	0.4138	0.046*
H8B	0.3452	0.4964	0.4841	0.046*
C9	0.2144 (3)	0.3769 (3)	0.41323 (12)	0.0337 (5)
C10	0.1169 (2)	0.2822 (4)	0.46142 (13)	0.0359 (5)
H10A	0.0340	0.2493	0.4354	0.043*
H10B	0.0919	0.3715	0.4976	0.043*
C11	0.1739 (3)	0.1065 (3)	0.49515 (14)	0.0400 (6)
H11A	0.1095	0.0603	0.5292	0.048*
H11B	0.1842	0.0088	0.4600	0.048*
C12	0.1583 (3)	0.5624 (4)	0.38954 (16)	0.0529 (7)
H12A	0.2230	0.6233	0.3597	0.079*
H12B	0.1421	0.6415	0.4293	0.079*
H12C	0.0737	0.5423	0.3643	0.079*
N1	0.5510 (2)	0.3157 (3)	0.75037 (10)	0.0354 (5)
N2	0.4744 (2)	0.1602 (3)	0.64825 (10)	0.0334 (4)
N3	0.6521 (2)	0.0517 (4)	0.71160 (12)	0.0510 (6)
H3A	0.6596	−0.0397	0.6820	0.061*
H3B	0.7081	0.0588	0.7469	0.061*
N4	0.2904 (2)	0.2682 (3)	0.58727 (10)	0.0355 (5)
H4	0.2173	0.3370	0.5872	0.043*
O1	0.23817 (18)	0.2603 (3)	0.35549 (9)	0.0420 (4)
H1	0.1654	0.2413	0.3342	0.063*
Br1	0.23506 (4)	0.62118 (5)	0.671478 (18)	0.06510 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0334 (12)	0.0391 (13)	0.0292 (12)	0.0023 (10)	−0.0052 (10)	−0.0036 (10)
C2	0.0362 (13)	0.0361 (12)	0.0311 (12)	−0.0024 (10)	0.0010 (10)	−0.0052 (10)
C3	0.0341 (13)	0.0357 (12)	0.0330 (12)	0.0048 (10)	−0.0012 (10)	−0.0026 (10)
C4	0.0305 (12)	0.0357 (13)	0.0261 (11)	−0.0010 (9)	−0.0015 (9)	0.0012 (9)
C5	0.0625 (19)	0.0506 (17)	0.0523 (18)	0.0074 (14)	−0.0080 (15)	−0.0204 (14)
C6	0.0397 (14)	0.0341 (13)	0.0336 (13)	0.0029 (10)	−0.0131 (10)	−0.0028 (10)
C7	0.0305 (12)	0.0488 (15)	0.0318 (12)	0.0033 (10)	−0.0085 (10)	−0.0130 (11)
C8	0.0392 (14)	0.0455 (14)	0.0315 (12)	−0.0098 (11)	0.0002 (10)	−0.0048 (11)
C9	0.0378 (13)	0.0344 (12)	0.0289 (12)	0.0038 (10)	−0.0043 (10)	−0.0023 (10)
C10	0.0308 (12)	0.0419 (14)	0.0346 (12)	0.0000 (10)	−0.0085 (10)	0.0023 (11)
C11	0.0418 (14)	0.0376 (14)	0.0402 (14)	−0.0080 (11)	−0.0122 (11)	0.0056 (11)
C12	0.070 (2)	0.0410 (15)	0.0473 (17)	0.0115 (14)	0.0002 (15)	0.0079 (13)
N1	0.0342 (11)	0.0412 (11)	0.0306 (10)	0.0010 (9)	−0.0056 (8)	−0.0077 (9)
N2	0.0359 (11)	0.0374 (11)	0.0267 (10)	0.0035 (8)	−0.0071 (8)	−0.0059 (8)
N3	0.0541 (14)	0.0575 (14)	0.0405 (12)	0.0239 (12)	−0.0226 (11)	−0.0177 (11)
N4	0.0321 (10)	0.0446 (12)	0.0297 (10)	0.0073 (9)	−0.0075 (8)	−0.0030 (9)
O1	0.0410 (10)	0.0525 (11)	0.0319 (9)	0.0119 (8)	−0.0100 (7)	−0.0119 (8)
Br1	0.0679 (3)	0.0608 (2)	0.0659 (3)	0.03307 (16)	−0.01891 (17)	−0.01908 (15)

Geometric parameters (Å, º) top

C1—N3	1.335 (3)	C7—H7B	0.9900
C1—N2	1.340 (3)	C8—C9	1.526 (3)
C1—N1	1.349 (3)	C8—H8A	0.9900
C2—N1	1.352 (3)	C8—H8B	0.9900
C2—C3	1.366 (3)	C9—O1	1.430 (3)
C2—C5	1.493 (4)	C9—C12	1.514 (4)
C3—C4	1.405 (3)	C9—C10	1.525 (3)
C3—Br1	1.891 (2)	C10—C11	1.529 (3)
C4—N2	1.331 (3)	C10—H10A	0.9900
C4—N4	1.351 (3)	C10—H10B	0.9900
C5—H5A	0.9800	C11—H11A	0.9900
C5—H5B	0.9800	C11—H11B	0.9900
C5—H5C	0.9800	C12—H12A	0.9800
C6—N4	1.457 (3)	C12—H12B	0.9800
C6—C11	1.517 (3)	C12—H12C	0.9800
C6—C7	1.518 (4)	N3—H3A	0.8800
C6—H6	1.0000	N3—H3B	0.8800
C7—C8	1.523 (4)	N4—H4	0.8800
C7—H7A	0.9900	O1—H1	0.8400

N3—C1—N2	116.8 (2)	H8A—C8—H8B	107.8
N3—C1—N1	116.6 (2)	O1—C9—C12	109.9 (2)
N2—C1—N1	126.6 (2)	O1—C9—C10	110.1 (2)
N1—C2—C3	120.5 (2)	C12—C9—C10	110.3 (2)
N1—C2—C5	115.7 (2)	O1—C9—C8	104.89 (19)
C3—C2—C5	123.8 (2)	C12—C9—C8	111.0 (2)
C2—C3—C4	119.2 (2)	C10—C9—C8	110.5 (2)
C2—C3—Br1	121.01 (19)	C9—C10—C11	113.6 (2)
C4—C3—Br1	119.76 (17)	C9—C10—H10A	108.8
N2—C4—N4	118.2 (2)	C11—C10—H10A	108.8
N2—C4—C3	120.7 (2)	C9—C10—H10B	108.8
N4—C4—C3	121.1 (2)	C11—C10—H10B	108.8
C2—C5—H5A	109.5	H10A—C10—H10B	107.7
C2—C5—H5B	109.5	C6—C11—C10	112.2 (2)
H5A—C5—H5B	109.5	C6—C11—H11A	109.2
C2—C5—H5C	109.5	C10—C11—H11A	109.2
H5A—C5—H5C	109.5	C6—C11—H11B	109.2
H5B—C5—H5C	109.5	C10—C11—H11B	109.2
N4—C6—C11	109.1 (2)	H11A—C11—H11B	107.9
N4—C6—C7	110.6 (2)	C9—C12—H12A	109.5
C11—C6—C7	109.7 (2)	C9—C12—H12B	109.5
N4—C6—H6	109.1	H12A—C12—H12B	109.5
C11—C6—H6	109.1	C9—C12—H12C	109.5
C7—C6—H6	109.1	H12A—C12—H12C	109.5
C6—C7—C8	111.2 (2)	H12B—C12—H12C	109.5
C6—C7—H7A	109.4	C1—N1—C2	116.5 (2)
C8—C7—H7A	109.4	C4—N2—C1	116.4 (2)
C6—C7—H7B	109.4	C1—N3—H3A	120.0
C8—C7—H7B	109.4	C1—N3—H3B	120.0
H7A—C7—H7B	108.0	H3A—N3—H3B	120.0
C7—C8—C9	113.2 (2)	C4—N4—C6	124.3 (2)
C7—C8—H8A	108.9	C4—N4—H4	117.8
C9—C8—H8A	108.9	C6—N4—H4	117.8
C7—C8—H8B	108.9	C9—O1—H1	109.5
C9—C8—H8B	108.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.88	2.03	2.828 (3)	151
O1—H1···N1ⁱⁱ	0.84	2.02	2.803 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₉BrN₄O
M_r	315.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	198
a, b, c (Å)	9.9514 (18), 7.1879 (11), 19.566 (4)
β (°)	91.053 (3)
V (Å³)	1399.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.93
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Siemens P4 with APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.758, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	8853, 3251, 2500
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.05
No. of reflections	3251
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.77

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-32 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.88	2.03	2.828 (3)	150.5
O1—H1···N1ⁱⁱ	0.84	2.02	2.803 (3)	154.5

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Melguizo, M., Quesada, A., Low, J. N. & Glidewell, C. (2003). Acta Cryst. B59, 263–276. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page o2374

doi:10.1107/S1600536809035533

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