2-Amino-4,6-dimethyl­pyrimidinium chloro­acetate

Lin, C.-H.; Liu, N.-S.; Jian, F.-F.

doi:10.1107/S1600536809044444

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2913

https://doi.org/10.1107/S1600536809044444

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2-Amino-4,6-dimethylpyrimidinium chloroacetate

Cui-Hua Lin,^a Nai-Sheng Liu ^b and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bJournal Editorial Department, Weifang University, Weifang 261061, People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 23 October 2009; accepted 26 October 2009; online 31 October 2009)

There are two cations and two anions in the asymmetric unit of the title compound, C₆H₁₀N₃⁺·C₂H₂ClO₂⁻. In the crystal, the components are linked by intermolecular N—H⋯O and N—H⋯N hydrogen bonds to form a two-dimensional network. Additional stabilization is provided by weak intermolecular C—H⋯O interactions.

Related literature

For background to pyrimidine derivatives, see: Xue et al. (1993 ); Hemamalini et al. (2005 ).

Experimental

Crystal data

C₆H₁₀N₃⁺·C₂H₂ClO₂⁻
M_r = 217.66
Triclinic, $[P \overline 1]$
a = 4.4560 (9) Å
b = 12.302 (3) Å
c = 19.441 (4) Å
α = 92.90 (3)°
β = 96.53 (3)°
γ = 91.15 (3)°
V = 1057.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
10303 measured reflections
4761 independent reflections
3452 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.195
S = 1.08
4761 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3ⁱ	0.86	2.14	2.999 (3)	177
N1—H1B⋯O3ⁱⁱ	0.86	1.98	2.830 (3)	173
N2—H2A⋯O4ⁱⁱ	0.86	1.74	2.593 (3)	175
N4—H4A⋯N6ⁱⁱⁱ	0.86	2.19	3.046 (3)	175
N4—H4B⋯O1^iv	0.86	2.00	2.851 (3)	173
N5—H5A⋯O2^iv	0.86	1.75	2.606 (3)	174
C1—H1C⋯O4ⁱⁱ	0.96	2.56	3.355 (4)	140
C7—H7A⋯O2^iv	0.96	2.57	3.355 (4)	139
Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x, -y, -z+1; (iv) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 I, global. DOI: https://doi.org/10.1107/S1600536809044444/hb5174sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044444/hb5174Isup2.hkl

checkCIF report

Comment top

As useful precursors to potentially bioactive pyrimidine derivatives, methylpyrimidine has attracted considerable attention for many years (Xue et al., 1993). In recent years, new complexes of pyrimidine have been synthesized (Hemamalini et al., 2005). The title compound(I), was synthesized and we report herein its crystal structure (Fig. 1).

There are two 2-amino-4,6-dimethylpyrimidine cations and two chloracetate anions in the asymmetric unit. In the crystal structure, cations and anions are linked by intermolecular N—H···O and N—H···N hydrogen bonds to form a two-dimensional network. Additional stabilization is provided by weak intermolecular C—H···O interactions.

Related literature top

For background o pyrimidine derivatives, see: Xue et al. (1993); Hemamalini et al. (2005).

Experimental top

A mixture of guanidine hydrochloride (0.1 mol), acetyl acetone (0.2 mol), sodium carbonate (0.03 mol) and 2-chloroacetic acid (0.1 mol) was stirred with water (30 ml) for 3 h to afford the title compound (yield 67%). Colourless blocks of (I) were obtained by recrystallization of the title compound from water at room temperature.

Structure description top

For background o pyrimidine derivatives, see: Xue et al. (1993); Hemamalini et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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) showing 30% probability displacement ellipsoids.

2-Amino-4,6-dimethylpyrimidinium chloroacetate top

Crystal data top

C₆H₁₀N₃⁺·C₂H₂ClO₂⁻	Z = 4
M_r = 217.66	F(000) = 456
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.4560 (9) Å	Cell parameters from 3452 reflections
b = 12.302 (3) Å	θ = 3.2–27.5°
c = 19.441 (4) Å	µ = 0.34 mm⁻¹
α = 92.90 (3)°	T = 293 K
β = 96.53 (3)°	Block, colourless
γ = 91.15 (3)°	0.20 × 0.15 × 0.11 mm
V = 1057.1 (4) Å³

Data collection top

Bruker SMART CCD diffractometer	3452 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −5→5
10303 measured reflections	k = −15→15
4761 independent 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1056P)² + 0.3945P] where P = (F_o² + 2F_c²)/3
4761 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₆H₁₀N₃⁺·C₂H₂ClO₂⁻	γ = 91.15 (3)°
M_r = 217.66	V = 1057.1 (4) Å³
Triclinic, P1	Z = 4
a = 4.4560 (9) Å	Mo Kα radiation
b = 12.302 (3) Å	µ = 0.34 mm⁻¹
c = 19.441 (4) Å	T = 293 K
α = 92.90 (3)°	0.20 × 0.15 × 0.11 mm
β = 96.53 (3)°

Data collection top

Bruker SMART CCD diffractometer	3452 reflections with I > 2σ(I)
10303 measured reflections	R_int = 0.028
4761 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.08	Δρ_max = 0.42 e Å⁻³
4761 reflections	Δρ_min = −0.43 e Å⁻³
253 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	0.92264 (17)	0.01264 (6)	0.17209 (4)	0.0623 (2)
O4	0.7689 (5)	0.14297 (17)	−0.00572 (10)	0.0681 (6)
C16	0.8811 (6)	0.13347 (19)	0.05672 (13)	0.0463 (5)
O3	1.0794 (5)	0.19170 (18)	0.08873 (11)	0.0742 (7)
C15	0.7353 (7)	0.0407 (2)	0.09016 (14)	0.0616 (7)
H15A	0.7320	−0.0243	0.0596	0.074*
H15B	0.5276	0.0584	0.0954	0.074*
Cl2	0.8148 (2)	0.60659 (7)	0.34169 (5)	0.0862 (3)
O2	0.9854 (5)	0.38470 (15)	0.37047 (10)	0.0594 (5)
C14	0.8160 (6)	0.4192 (2)	0.41493 (13)	0.0497 (6)
O1	0.7445 (6)	0.36870 (18)	0.46320 (12)	0.0798 (7)
C13	0.6862 (8)	0.5308 (2)	0.40795 (16)	0.0632 (7)
H13A	0.7342	0.5722	0.4518	0.076*
H13B	0.4680	0.5230	0.3993	0.076*
N5	0.1724 (4)	0.18552 (15)	0.37450 (10)	0.0418 (4)
H5A	0.1093	0.2511	0.3762	0.050*
N6	0.1954 (5)	0.01175 (16)	0.42234 (10)	0.0467 (5)
C10	0.1065 (6)	0.11536 (19)	0.42261 (12)	0.0436 (5)
C9	0.4323 (6)	0.0461 (2)	0.32177 (13)	0.0502 (6)
H9A	0.5446	0.0210	0.2870	0.060*
C12	0.3572 (6)	−0.02223 (19)	0.37232 (13)	0.0477 (5)
C8	0.3363 (5)	0.15178 (19)	0.32440 (12)	0.0430 (5)
N4	−0.0552 (6)	0.15065 (18)	0.47176 (12)	0.0610 (6)
H4A	−0.1012	0.1075	0.5026	0.073*
H4B	−0.1145	0.2167	0.4729	0.073*
C7	0.4002 (7)	0.2310 (2)	0.27171 (13)	0.0554 (6)
H7A	0.3149	0.2998	0.2829	0.083*
H7B	0.3119	0.2038	0.2266	0.083*
H7C	0.6146	0.2402	0.2718	0.083*
C11	0.4550 (8)	−0.1383 (2)	0.37303 (18)	0.0689 (8)
H11A	0.3841	−0.1721	0.4118	0.103*
H11B	0.6715	−0.1400	0.3770	0.103*
H11C	0.3719	−0.1768	0.3308	0.103*
N2	0.0615 (5)	0.69331 (16)	0.07225 (10)	0.0457 (5)
H2A	0.1088	0.7470	0.0486	0.055*
N3	−0.2359 (5)	0.53279 (17)	0.07940 (11)	0.0489 (5)
C6	−0.0956 (6)	0.5215 (2)	0.14272 (13)	0.0493 (6)
N1	−0.2951 (5)	0.63311 (18)	−0.01745 (11)	0.0566 (6)
H1A	−0.4349	0.5876	−0.0354	0.068*
H1B	−0.2464	0.6878	−0.0401	0.068*
C4	−0.1547 (5)	0.61899 (19)	0.04524 (12)	0.0443 (5)
C2	0.2013 (5)	0.6821 (2)	0.13654 (13)	0.0472 (5)
C3	0.1249 (6)	0.5956 (2)	0.17351 (14)	0.0520 (6)
H3B	0.2183	0.5868	0.2181	0.062*
C1	0.4302 (6)	0.7682 (2)	0.16441 (15)	0.0594 (7)
H1C	0.4485	0.8204	0.1300	0.089*
H1D	0.6220	0.7355	0.1759	0.089*
H1E	0.3673	0.8039	0.2052	0.089*
C5	−0.1883 (8)	0.4234 (2)	0.17923 (16)	0.0657 (8)
H5B	−0.3422	0.3821	0.1499	0.099*
H5C	−0.2654	0.4466	0.2216	0.099*
H5D	−0.0162	0.3788	0.1896	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0689 (4)	0.0673 (4)	0.0516 (4)	−0.0052 (3)	0.0041 (3)	0.0202 (3)
O4	0.0883 (15)	0.0633 (12)	0.0497 (11)	−0.0230 (11)	−0.0076 (10)	0.0170 (9)
C16	0.0500 (13)	0.0415 (12)	0.0478 (13)	−0.0017 (10)	0.0065 (10)	0.0057 (10)
O3	0.0887 (15)	0.0727 (14)	0.0573 (12)	−0.0334 (12)	−0.0100 (11)	0.0213 (10)
C15	0.0666 (17)	0.0649 (17)	0.0515 (15)	−0.0184 (14)	−0.0035 (12)	0.0182 (13)
Cl2	0.1195 (7)	0.0527 (4)	0.0972 (7)	0.0286 (4)	0.0432 (5)	0.0302 (4)
O2	0.0773 (13)	0.0450 (10)	0.0609 (11)	0.0132 (9)	0.0229 (10)	0.0130 (8)
C14	0.0569 (14)	0.0407 (12)	0.0512 (14)	0.0017 (11)	0.0031 (11)	0.0057 (10)
O1	0.1139 (19)	0.0612 (13)	0.0750 (14)	0.0228 (12)	0.0437 (13)	0.0261 (11)
C13	0.0779 (19)	0.0520 (15)	0.0638 (17)	0.0163 (14)	0.0193 (14)	0.0105 (13)
N5	0.0532 (11)	0.0323 (9)	0.0405 (10)	0.0009 (8)	0.0054 (8)	0.0097 (7)
N6	0.0617 (12)	0.0356 (10)	0.0449 (10)	0.0052 (9)	0.0101 (9)	0.0118 (8)
C10	0.0554 (13)	0.0375 (11)	0.0387 (11)	0.0014 (10)	0.0054 (9)	0.0096 (9)
C9	0.0628 (15)	0.0461 (13)	0.0436 (12)	0.0069 (11)	0.0116 (11)	0.0071 (10)
C12	0.0581 (14)	0.0393 (12)	0.0463 (13)	0.0068 (10)	0.0044 (10)	0.0076 (9)
C8	0.0476 (12)	0.0429 (12)	0.0383 (11)	−0.0006 (9)	0.0008 (9)	0.0096 (9)
N4	0.0932 (17)	0.0420 (11)	0.0545 (13)	0.0128 (11)	0.0300 (12)	0.0158 (9)
C7	0.0702 (16)	0.0512 (14)	0.0475 (13)	−0.0013 (12)	0.0140 (12)	0.0159 (11)
C11	0.094 (2)	0.0426 (14)	0.074 (2)	0.0197 (14)	0.0196 (17)	0.0118 (13)
N2	0.0515 (11)	0.0420 (10)	0.0458 (11)	−0.0001 (9)	0.0120 (8)	0.0094 (8)
N3	0.0563 (12)	0.0423 (10)	0.0505 (12)	0.0016 (9)	0.0129 (9)	0.0112 (9)
C6	0.0574 (14)	0.0451 (12)	0.0490 (13)	0.0119 (11)	0.0147 (11)	0.0138 (10)
N1	0.0679 (14)	0.0504 (12)	0.0507 (12)	−0.0145 (11)	0.0014 (10)	0.0147 (9)
C4	0.0480 (12)	0.0426 (12)	0.0443 (12)	0.0013 (10)	0.0116 (10)	0.0070 (9)
C2	0.0444 (12)	0.0497 (13)	0.0494 (13)	0.0098 (10)	0.0111 (10)	0.0051 (10)
C3	0.0547 (14)	0.0561 (14)	0.0472 (13)	0.0110 (12)	0.0089 (11)	0.0118 (11)
C1	0.0571 (15)	0.0599 (16)	0.0599 (16)	0.0006 (13)	0.0025 (12)	0.0015 (13)
C5	0.085 (2)	0.0530 (15)	0.0628 (17)	0.0037 (14)	0.0126 (15)	0.0231 (13)

Geometric parameters (Å, º) top

Cl1—C15	1.766 (3)	C7—H7A	0.9600
O4—C16	1.271 (3)	C7—H7B	0.9600
C16—O3	1.219 (3)	C7—H7C	0.9600
C16—C15	1.512 (3)	C11—H11A	0.9600
C15—H15A	0.9700	C11—H11B	0.9600
C15—H15B	0.9700	C11—H11C	0.9600
Cl2—C13	1.767 (3)	N2—C2	1.347 (3)
O2—C14	1.273 (3)	N2—C4	1.357 (3)
C14—O1	1.220 (3)	N2—H2A	0.8600
C14—C13	1.507 (4)	N3—C6	1.331 (3)
C13—H13A	0.9700	N3—C4	1.344 (3)
C13—H13B	0.9700	C6—C3	1.389 (4)
N5—C8	1.337 (3)	C6—C5	1.505 (3)
N5—C10	1.356 (3)	N1—C4	1.326 (3)
N5—H5A	0.8600	N1—H1A	0.8600
N6—C12	1.331 (3)	N1—H1B	0.8600
N6—C10	1.342 (3)	C2—C3	1.372 (4)
C10—N4	1.322 (3)	C2—C1	1.493 (4)
C9—C8	1.378 (4)	C3—H3B	0.9300
C9—C12	1.389 (3)	C1—H1C	0.9600
C9—H9A	0.9300	C1—H1D	0.9600
C12—C11	1.501 (4)	C1—H1E	0.9600
C8—C7	1.495 (3)	C5—H5B	0.9600
N4—H4A	0.8600	C5—H5C	0.9600
N4—H4B	0.8600	C5—H5D	0.9600

O3—C16—O4	126.0 (2)	C8—C7—H7C	109.5
O3—C16—C15	121.5 (2)	H7A—C7—H7C	109.5
O4—C16—C15	112.5 (2)	H7B—C7—H7C	109.5
C16—C15—Cl1	113.42 (19)	C12—C11—H11A	109.5
C16—C15—H15A	108.9	C12—C11—H11B	109.5
Cl1—C15—H15A	108.9	H11A—C11—H11B	109.5
C16—C15—H15B	108.9	C12—C11—H11C	109.5
Cl1—C15—H15B	108.9	H11A—C11—H11C	109.5
H15A—C15—H15B	107.7	H11B—C11—H11C	109.5
O1—C14—O2	125.4 (2)	C2—N2—C4	119.3 (2)
O1—C14—C13	116.1 (2)	C2—N2—H2A	120.4
O2—C14—C13	118.5 (2)	C4—N2—H2A	120.4
C14—C13—Cl2	115.3 (2)	C6—N3—C4	117.5 (2)
C14—C13—H13A	108.5	N3—C6—C3	122.1 (2)
Cl2—C13—H13A	108.5	N3—C6—C5	116.2 (2)
C14—C13—H13B	108.5	C3—C6—C5	121.7 (2)
Cl2—C13—H13B	108.5	C4—N1—H1A	120.0
H13A—C13—H13B	107.5	C4—N1—H1B	120.0
C8—N5—C10	119.4 (2)	H1A—N1—H1B	120.0
C8—N5—H5A	120.3	N1—C4—N3	118.6 (2)
C10—N5—H5A	120.3	N1—C4—N2	118.3 (2)
C12—N6—C10	117.6 (2)	N3—C4—N2	123.1 (2)
N4—C10—N6	118.5 (2)	N2—C2—C3	119.7 (2)
N4—C10—N5	118.3 (2)	N2—C2—C1	116.9 (2)
N6—C10—N5	123.2 (2)	C3—C2—C1	123.4 (2)
C8—C9—C12	118.4 (2)	C2—C3—C6	118.4 (2)
C8—C9—H9A	120.8	C2—C3—H3B	120.8
C12—C9—H9A	120.8	C6—C3—H3B	120.8
N6—C12—C9	121.8 (2)	C2—C1—H1C	109.5
N6—C12—C11	116.7 (2)	C2—C1—H1D	109.5
C9—C12—C11	121.5 (2)	H1C—C1—H1D	109.5
N5—C8—C9	119.7 (2)	C2—C1—H1E	109.5
N5—C8—C7	117.8 (2)	H1C—C1—H1E	109.5
C9—C8—C7	122.5 (2)	H1D—C1—H1E	109.5
C10—N4—H4A	120.0	C6—C5—H5B	109.5
C10—N4—H4B	120.0	C6—C5—H5C	109.5
H4A—N4—H4B	120.0	H5B—C5—H5C	109.5
C8—C7—H7A	109.5	C6—C5—H5D	109.5
C8—C7—H7B	109.5	H5B—C5—H5D	109.5
H7A—C7—H7B	109.5	H5C—C5—H5D	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.14	2.999 (3)	177
N1—H1B···O3ⁱⁱ	0.86	1.98	2.830 (3)	173
N2—H2A···O4ⁱⁱ	0.86	1.74	2.593 (3)	175
N4—H4A···N6ⁱⁱⁱ	0.86	2.19	3.046 (3)	175
N4—H4B···O1^iv	0.86	2.00	2.851 (3)	173
N5—H5A···O2^iv	0.86	1.75	2.606 (3)	174
C1—H1C···O4ⁱⁱ	0.96	2.56	3.355 (4)	140
C7—H7A···O2^iv	0.96	2.57	3.355 (4)	139

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

Experimental details

Crystal data
Chemical formula	C₆H₁₀N₃⁺·C₂H₂ClO₂⁻
M_r	217.66
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	4.4560 (9), 12.302 (3), 19.441 (4)
α, β, γ (°)	92.90 (3), 96.53 (3), 91.15 (3)
V (Å³)	1057.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10303, 4761, 3452
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.195, 1.08
No. of reflections	4761
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.43

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
N1—H1A···N3ⁱ	0.86	2.14	2.999 (3)	177
N1—H1B···O3ⁱⁱ	0.86	1.98	2.830 (3)	173
N2—H2A···O4ⁱⁱ	0.86	1.74	2.593 (3)	175
N4—H4A···N6ⁱⁱⁱ	0.86	2.19	3.046 (3)	175
N4—H4B···O1^iv	0.86	2.00	2.851 (3)	173
N5—H5A···O2^iv	0.86	1.75	2.606 (3)	174
C1—H1C···O4ⁱⁱ	0.96	2.56	3.355 (4)	140
C7—H7A···O2^iv	0.96	2.57	3.355 (4)	139

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hemamalini, M., Muthiah, P. T., Rychlewska, U. & Plutecka, A. (2005). Acta Cryst. C61, o95–o97. 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
Xue, S. J., Zhang, A. D. & Wang, H. T. (1993). Chemical Reagents, 15, 181. Google Scholar

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Volume 65| Part 11| November 2009| Page o2913

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