3-(2,6-Dimethyl­anilino)imidazo[1,2-a]pyridin-1-ium perchlorate

Nichol, G.S.; Sharma, A.; Li, H.-Y.

doi:10.1107/S1600536811014735

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1224

doi:10.1107/S1600536811014735

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3-(2,6-Dimethylanilino)imidazo[1,2-a]pyridin-1-ium perchlorate

Gary S. Nichol,^a ^* Anuj Sharma ^b and Hong-Yu Li ^b

^aDepartment of Chemistry and Biochemistry, 1306 East University Boulevard, University of Arizona, Tucson, AZ 85721, USA, and ^bSouthwest Center for Drug Discovery and Development, College of Pharmacy, BIO5 Institute, University of Arizona, Tucson, AZ 85721, USA
^*Correspondence e-mail: gsnichol@email.arizona.edu

(Received 12 April 2011; accepted 20 April 2011; online 29 April 2011)

The structure of the organic cation in the title compound, C₁₅H₁₆N₃⁺·ClO₄⁻, contains two essentially planar rings. Mean planes fitted through all non-H atoms of each ring system have an r.m.s. deviation of 0.019 Å for the imidazole-based ring and 0.016 Å for the 2,6-dimethylphenyl ring. The angle between the two planes is 86.76 (2)°. In the crystal structure, N—H⋯O interactions form a one-dimensional chain, which propagates in the b-axis direction. C—H⋯O interactions are also found in the crystal packing.

Related literature

For background information on the Groebke–Blackburn synthesis, see: Bienaymé & Bouzid (1998 ); Blackburn et al. (1998 ); Groebke et al. (1998 ). For details of the chemical synthesis, see: Nichol et al. (2011 ); Sharma & Li (2011 ). For information on graph-set notation to describe hydrogen-bonding motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₆N₃⁺·ClO₄⁻
M_r = 337.76
Triclinic, $[P \overline 1]$
a = 8.6347 (3) Å
b = 8.7663 (3) Å
c = 11.5155 (4) Å
α = 70.668 (2)°
β = 73.131 (2)°
γ = 72.679 (2)°
V = 767.24 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.26 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.932, T_max = 0.957
27864 measured reflections
8640 independent reflections
6871 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.05
8640 reflections
272 parameters
All H-atom parameters refined
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.869 (16)	1.955 (17)	2.8169 (10)	170.8 (15)
N3—H3N⋯O3	0.832 (16)	2.216 (15)	2.8899 (10)	138.3 (14)
C2—H2⋯O2ⁱⁱ	0.911 (14)	2.547 (14)	3.3826 (11)	152.8 (12)
C3—H3⋯O4ⁱⁱ	0.971 (15)	2.559 (15)	3.2893 (12)	132.0 (11)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014735/kj2175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014735/kj2175Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014735/kj2175Isup3.cdx

checkCIF report

Comment top

The Groebke–Blackburn reaction is the most popular way to prepare imidazo-azines from 2-aminoazines in a single-step (Groebke et al., 1998; Bienaymé & Bouzid, 1998; Blackburn et al., 1998). We have recently reported developments on this synthetic method (Nichol et al., 2011; Sharma & Li, 2011) and present here the crystal structure of the title compound, determined as part of a larger study.

The asymmetric unit of the title compound is shown in Fig. 1. Molecular dimensions are unexceptional. Both ring systems are essentially planar (a mean plane fitted through atoms N1, N2, N3 C1 > C7 has an r.m.s. deviation of 0.019 Å; a mean plane fitted through atoms N3, C8 > C15 has an r.m.s. deviation of 0.016 Å) and the angle between both planes is 86.76 (2)°.

In the crystal, N—H···O interactions form a one-dimensional C²₂(9) chain (Bernstein et al. 1995), which propagates in the b-axis direction (Fig. 2). C—H···O interactions are also found in the crystal packing.

Related literature top

For background information on the Groebke–Blackburn synthesis, see: Bienaymé & Bouzid (1998); Blackburn et al. (1998); Groebke et al. (1998). For details of the chemical synthesis, see: Nichol et al., 2011; Sharma & Li (2011). For information on graph-set notation to describe hydrogen-bonding motifs, see: Bernstein et al. (1995).

Experimental top

The synthesis is described in Sharma & Li (2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. N—H···O interactions (dotted blue lines; dotted red lines indicate continuation) in the title compound.

3-(2,6-Dimethylanilino)imidazo[1,2-a]pyridin-1-ium perchlorate top

Crystal data top

C₁₅H₁₆N₃⁺·ClO₄⁻	Z = 2
M_r = 337.76	F(000) = 352
Triclinic, P1	D_x = 1.462 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6347 (3) Å	Cell parameters from 8544 reflections
b = 8.7663 (3) Å	θ = 2.5–39.0°
c = 11.5155 (4) Å	µ = 0.27 mm⁻¹
α = 70.668 (2)°	T = 100 K
β = 73.131 (2)°	Block, colourless
γ = 72.679 (2)°	0.26 × 0.16 × 0.16 mm
V = 767.24 (5) Å³

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	8640 independent reflections
Radiation source: fine-focus sealed tube with Miracol optics	6871 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 38.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
T_min = 0.932, T_max = 0.957	k = −15→15
27864 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0581P)² + 0.1118P] where P = (F_o² + 2F_c²)/3
8640 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₅H₁₆N₃⁺·ClO₄⁻	γ = 72.679 (2)°
M_r = 337.76	V = 767.24 (5) Å³
Triclinic, P1	Z = 2
a = 8.6347 (3) Å	Mo Kα radiation
b = 8.7663 (3) Å	µ = 0.27 mm⁻¹
c = 11.5155 (4) Å	T = 100 K
α = 70.668 (2)°	0.26 × 0.16 × 0.16 mm
β = 73.131 (2)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	8640 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6871 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.957	R_int = 0.031
27864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	All H-atom parameters refined
S = 1.05	Δρ_max = 0.61 e Å⁻³
8640 reflections	Δρ_min = −0.51 e Å⁻³
272 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
N1	0.98956 (8)	0.60185 (8)	0.27803 (6)	0.01285 (10)
N2	0.85450 (9)	0.82744 (9)	0.33586 (7)	0.01631 (12)
H2N	0.825 (2)	0.904 (2)	0.3751 (15)	0.032 (4)*
N3	0.82987 (9)	0.59792 (9)	0.13756 (7)	0.01541 (11)
H3N	0.782 (2)	0.5193 (19)	0.1717 (14)	0.030 (4)*
C1	1.10989 (10)	0.45913 (10)	0.27281 (8)	0.01559 (13)
H1	1.1040 (18)	0.3970 (17)	0.2222 (13)	0.021 (3)*
C2	1.22970 (11)	0.41819 (11)	0.33968 (8)	0.01768 (14)
H2	1.3107 (17)	0.3243 (17)	0.3371 (13)	0.021 (3)*
C3	1.23050 (11)	0.52108 (11)	0.41221 (8)	0.01805 (14)
H3	1.3177 (18)	0.4918 (18)	0.4584 (14)	0.026 (3)*
C4	1.11017 (11)	0.66267 (11)	0.41743 (8)	0.01665 (13)
H4	1.1091 (17)	0.7333 (17)	0.4609 (13)	0.022 (3)*
C5	0.98717 (10)	0.70098 (9)	0.34900 (7)	0.01399 (12)
C6	0.77067 (10)	0.80959 (10)	0.25805 (8)	0.01618 (13)
H6	0.6720 (18)	0.8831 (18)	0.2376 (14)	0.025 (3)*
C7	0.85317 (10)	0.66985 (9)	0.22032 (7)	0.01359 (12)
C8	0.77759 (10)	0.70835 (9)	0.02641 (7)	0.01420 (12)
C9	0.62087 (11)	0.72027 (11)	0.00791 (8)	0.01716 (13)
C10	0.57589 (12)	0.82519 (12)	−0.10399 (9)	0.02081 (15)
H10	0.4688 (18)	0.8271 (17)	−0.1195 (13)	0.023 (3)*
C11	0.68217 (13)	0.91810 (12)	−0.19433 (9)	0.02220 (16)
H11	0.657 (2)	0.9887 (19)	−0.2776 (15)	0.033 (4)*
C12	0.83699 (12)	0.90525 (11)	−0.17397 (8)	0.02083 (15)
H12	0.915 (2)	0.9649 (19)	−0.2370 (15)	0.032 (4)*
C13	0.88820 (11)	0.79974 (10)	−0.06457 (8)	0.01662 (13)
C14	0.50193 (13)	0.62394 (14)	0.10725 (10)	0.02599 (19)
H14A	0.549 (2)	0.498 (2)	0.1225 (15)	0.035 (4)*
H14B	0.483 (2)	0.655 (2)	0.1867 (16)	0.037 (4)*
H14C	0.394 (2)	0.652 (2)	0.0884 (16)	0.037 (4)*
C15	1.05888 (12)	0.78164 (13)	−0.04629 (9)	0.02178 (16)
H15A	1.0548 (18)	0.8453 (18)	0.0085 (14)	0.027 (4)*
H15B	1.135 (2)	0.819 (2)	−0.1279 (16)	0.036 (4)*
H15C	1.1063 (19)	0.6657 (19)	−0.0109 (14)	0.028 (4)*
Cl	0.65990 (2)	0.20252 (2)	0.419315 (17)	0.01454 (5)
O1	0.79691 (9)	0.07166 (9)	0.46174 (7)	0.02290 (13)
O2	0.60990 (9)	0.15985 (9)	0.32753 (7)	0.02488 (14)
O3	0.71409 (13)	0.35550 (10)	0.36274 (8)	0.03427 (19)
O4	0.52640 (10)	0.21967 (12)	0.52460 (7)	0.03483 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0136 (3)	0.0125 (2)	0.0123 (2)	−0.0019 (2)	−0.0038 (2)	−0.0031 (2)
N2	0.0182 (3)	0.0136 (3)	0.0171 (3)	−0.0008 (2)	−0.0050 (2)	−0.0054 (2)
N3	0.0204 (3)	0.0135 (3)	0.0136 (3)	−0.0049 (2)	−0.0072 (2)	−0.0011 (2)
C1	0.0161 (3)	0.0143 (3)	0.0155 (3)	−0.0001 (2)	−0.0046 (2)	−0.0047 (2)
C2	0.0157 (3)	0.0180 (3)	0.0183 (3)	0.0004 (3)	−0.0061 (3)	−0.0049 (3)
C3	0.0164 (3)	0.0210 (3)	0.0175 (3)	−0.0037 (3)	−0.0065 (3)	−0.0042 (3)
C4	0.0184 (3)	0.0180 (3)	0.0156 (3)	−0.0050 (3)	−0.0055 (3)	−0.0047 (3)
C5	0.0153 (3)	0.0135 (3)	0.0133 (3)	−0.0030 (2)	−0.0035 (2)	−0.0037 (2)
C6	0.0163 (3)	0.0144 (3)	0.0167 (3)	−0.0006 (2)	−0.0054 (2)	−0.0037 (2)
C7	0.0141 (3)	0.0132 (3)	0.0131 (3)	−0.0020 (2)	−0.0047 (2)	−0.0024 (2)
C8	0.0166 (3)	0.0133 (3)	0.0125 (3)	−0.0031 (2)	−0.0051 (2)	−0.0018 (2)
C9	0.0175 (3)	0.0185 (3)	0.0154 (3)	−0.0046 (3)	−0.0059 (3)	−0.0018 (3)
C10	0.0213 (4)	0.0218 (4)	0.0188 (3)	−0.0018 (3)	−0.0104 (3)	−0.0020 (3)
C11	0.0290 (4)	0.0189 (3)	0.0161 (3)	−0.0023 (3)	−0.0094 (3)	0.0000 (3)
C12	0.0270 (4)	0.0178 (3)	0.0149 (3)	−0.0072 (3)	−0.0039 (3)	0.0006 (3)
C13	0.0187 (3)	0.0157 (3)	0.0148 (3)	−0.0048 (3)	−0.0028 (2)	−0.0030 (2)
C14	0.0204 (4)	0.0336 (5)	0.0227 (4)	−0.0128 (4)	−0.0065 (3)	0.0016 (4)
C15	0.0186 (4)	0.0249 (4)	0.0222 (4)	−0.0087 (3)	−0.0026 (3)	−0.0048 (3)
Cl	0.01653 (8)	0.01267 (7)	0.01320 (7)	−0.00157 (5)	−0.00390 (6)	−0.00279 (5)
O1	0.0223 (3)	0.0221 (3)	0.0274 (3)	0.0056 (2)	−0.0147 (3)	−0.0118 (3)
O2	0.0258 (3)	0.0247 (3)	0.0311 (4)	0.0006 (3)	−0.0171 (3)	−0.0124 (3)
O3	0.0591 (6)	0.0231 (3)	0.0265 (4)	−0.0231 (4)	−0.0188 (4)	0.0067 (3)
O4	0.0263 (4)	0.0410 (5)	0.0207 (3)	0.0058 (3)	0.0040 (3)	−0.0066 (3)

Geometric parameters (Å, º) top

N1—C1	1.3741 (10)	C8—C13	1.4039 (11)
N1—C5	1.3687 (10)	C9—C10	1.3966 (12)
N1—C7	1.3992 (10)	C9—C14	1.5071 (13)
N2—H2N	0.869 (16)	C10—H10	0.985 (14)
N2—C5	1.3408 (11)	C10—C11	1.3849 (14)
N2—C6	1.3740 (11)	C11—H11	0.999 (16)
N3—H3N	0.832 (16)	C11—C12	1.3891 (14)
N3—C7	1.3896 (10)	C12—H12	0.966 (16)
N3—C8	1.4262 (10)	C12—C13	1.3951 (12)
C1—H1	0.939 (14)	C13—C15	1.5034 (13)
C1—C2	1.3602 (12)	C14—H14A	1.033 (17)
C2—H2	0.911 (14)	C14—H14B	0.994 (17)
C2—C3	1.4203 (12)	C14—H14C	0.958 (17)
C3—H3	0.971 (15)	C15—H15A	0.958 (15)
C3—C4	1.3671 (12)	C15—H15B	0.994 (16)
C4—H4	0.912 (14)	C15—H15C	0.971 (15)
C4—C5	1.3999 (11)	Cl—O1	1.4528 (7)
C6—H6	0.941 (15)	Cl—O2	1.4375 (7)
C6—C7	1.3601 (11)	Cl—O3	1.4353 (8)
C8—C9	1.3985 (11)	Cl—O4	1.4239 (8)

C1—N1—C5	121.77 (7)	C8—C9—C10	118.57 (8)
C1—N1—C7	129.50 (7)	C8—C9—C14	120.81 (7)
C5—N1—C7	108.71 (6)	C10—C9—C14	120.61 (8)
H2N—N2—C5	123.8 (11)	C9—C10—H10	118.3 (8)
H2N—N2—C6	126.6 (11)	C9—C10—C11	121.14 (8)
C5—N2—C6	109.48 (7)	H10—C10—C11	120.4 (8)
H3N—N3—C7	114.8 (11)	C10—C11—H11	123.1 (9)
H3N—N3—C8	114.5 (11)	C10—C11—C12	119.44 (8)
C7—N3—C8	116.63 (7)	H11—C11—C12	117.3 (9)
N1—C1—H1	117.3 (9)	C11—C12—H12	121.1 (9)
N1—C1—C2	118.21 (7)	C11—C12—C13	121.33 (8)
H1—C1—C2	124.5 (9)	H12—C12—C13	117.5 (9)
C1—C2—H2	119.5 (9)	C8—C13—C12	118.23 (8)
C1—C2—C3	120.71 (8)	C8—C13—C15	121.02 (7)
H2—C2—C3	119.8 (9)	C12—C13—C15	120.74 (8)
C2—C3—H3	120.1 (9)	C9—C14—H14A	111.5 (9)
C2—C3—C4	120.84 (7)	C9—C14—H14B	108.0 (10)
H3—C3—C4	119.1 (9)	C9—C14—H14C	113.1 (10)
C3—C4—H4	123.1 (9)	H14A—C14—H14B	109.3 (13)
C3—C4—C5	117.33 (8)	H14A—C14—H14C	109.5 (14)
H4—C4—C5	119.6 (9)	H14B—C14—H14C	105.1 (14)
N1—C5—N2	107.30 (7)	C13—C15—H15A	110.8 (9)
N1—C5—C4	121.11 (7)	C13—C15—H15B	111.2 (10)
N2—C5—C4	131.58 (8)	C13—C15—H15C	109.7 (9)
N2—C6—H6	123.8 (9)	H15A—C15—H15B	108.4 (13)
N2—C6—C7	108.34 (7)	H15A—C15—H15C	109.6 (12)
H6—C6—C7	127.8 (9)	H15B—C15—H15C	107.1 (13)
N1—C7—N3	120.77 (7)	O1—Cl—O2	108.58 (4)
N1—C7—C6	106.16 (7)	O1—Cl—O3	109.13 (5)
N3—C7—C6	132.97 (7)	O1—Cl—O4	109.21 (5)
N3—C8—C9	120.05 (7)	O2—Cl—O3	109.54 (5)
N3—C8—C13	118.66 (7)	O2—Cl—O4	110.96 (6)
C9—C8—C13	121.27 (7)	O3—Cl—O4	109.39 (6)

C5—N1—C1—C2	−0.63 (12)	C1—N1—C7—C6	178.53 (8)
C7—N1—C1—C2	−179.04 (8)	C5—N1—C7—N3	176.88 (7)
N1—C1—C2—C3	−0.38 (13)	C5—N1—C7—C6	−0.04 (9)
C1—C2—C3—C4	0.61 (13)	C7—N3—C8—C9	−114.31 (9)
C2—C3—C4—C5	0.16 (13)	C7—N3—C8—C13	67.62 (10)
C6—N2—C5—N1	0.59 (9)	N3—C8—C9—C10	−177.75 (8)
C6—N2—C5—C4	−179.96 (9)	N3—C8—C9—C14	3.10 (13)
C1—N1—C5—N2	−179.04 (7)	C13—C8—C9—C10	0.27 (13)
C1—N1—C5—C4	1.44 (12)	C13—C8—C9—C14	−178.88 (9)
C7—N1—C5—N2	−0.34 (9)	C8—C9—C10—C11	−1.10 (14)
C7—N1—C5—C4	−179.86 (7)	C14—C9—C10—C11	178.05 (10)
C3—C4—C5—N1	−1.16 (12)	C9—C10—C11—C12	0.78 (15)
C3—C4—C5—N2	179.45 (9)	C10—C11—C12—C13	0.40 (15)
C5—N2—C6—C7	−0.62 (10)	C11—C12—C13—C8	−1.19 (14)
N2—C6—C7—N1	0.39 (9)	C11—C12—C13—C15	177.38 (9)
N2—C6—C7—N3	−175.99 (8)	N3—C8—C13—C12	178.90 (8)
C8—N3—C7—N1	−138.11 (8)	N3—C8—C13—C15	0.33 (12)
C8—N3—C7—C6	37.84 (13)	C9—C8—C13—C12	0.85 (13)
C1—N1—C7—N3	−4.55 (12)	C9—C8—C13—C15	−177.71 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.869 (16)	1.955 (17)	2.8169 (10)	170.8 (15)
N3—H3N···O3	0.832 (16)	2.216 (15)	2.8899 (10)	138.3 (14)
C2—H2···O2ⁱⁱ	0.911 (14)	2.547 (14)	3.3826 (11)	152.8 (12)
C3—H3···O4ⁱⁱ	0.971 (15)	2.559 (15)	3.2893 (12)	132.0 (11)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₃⁺·ClO₄⁻
M_r	337.76
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6347 (3), 8.7663 (3), 11.5155 (4)
α, β, γ (°)	70.668 (2), 73.131 (2), 72.679 (2)
V (Å³)	767.24 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.26 × 0.16 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	27864, 8640, 6871
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.877

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.05
No. of reflections	8640
No. of parameters	272
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.869 (16)	1.955 (17)	2.8169 (10)	170.8 (15)
N3—H3N···O3	0.832 (16)	2.216 (15)	2.8899 (10)	138.3 (14)
C2—H2···O2ⁱⁱ	0.911 (14)	2.547 (14)	3.3826 (11)	152.8 (12)
C3—H3···O4ⁱⁱ	0.971 (15)	2.559 (15)	3.2893 (12)	132.0 (11)

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

Acknowledgements

The diffractometer was purchased with funding from NSF grant No. CHE-0741837.

References

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