Bis[μ-N-(pyridin-2-ylmeth­yl)pyridin-3-amine-κ2N:N′]disilver(I) bis­(perchlorate) dimethyl sulfoxide disolvate

Moon, S.-H.; Park, K.-M.

doi:10.1107/S1600536813026585

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages m575-m576

doi:10.1107/S1600536813026585

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Bis[μ-N-(pyridin-2-ylmethyl)pyridin-3-amine-κ²N:N′]disilver(I) bis(perchlorate) dimethyl sulfoxide disolvate

Suk-Hee Moon ^a and Ki-Min Park ^b ^*

^aDepartment of Food & Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea, and ^bDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr

(Received 25 September 2013; accepted 26 September 2013; online 2 October 2013)

In the binuclear title compound, [Ag₂(C₁₁H₁₁N₃)₂](ClO₄)₂·2C₂H₆SO, the complex cation is centrosymmetric, with the unique Ag^I cation coordinated by two pyridine N atoms from two symmetry-related N-(pyridine-2-ylmethyl)pyridine-3-amine ligands in a geometry slightly distorted from linear [N—Ag—N = 170.78 (9)°], resulting in the formation of a 16-membered cyclic dimer. The two pyridine rings coordinating to the Ag^I atom are almost perpendicular to each other [dihedral angle = 87.73 (10)°]. Intermolecular Ag⋯O interactions [3.149 (3) and 2.686 (3) Å], N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions between the cyclic dimers and the anions or the solvent molecules lead to the formation of a three-dimensional supramolecular network.

CCDC reference: 963329

Related literature

For structures of Ag^I coordination polymers with symmetrical dipyridyl ligands, see: Lee et al. (2012 ); Leong & Vittal (2011 ); Park et al. (2010 ) and of Ag^I coordination polymers with unsymmetrical dipyridyl ligands, see: Moon & Park (2013 ); Zhang et al. (2013 ). For the synthesis of the ligand, see: Foxon et al. (2002 ); Lee et al. (2008 ).

Experimental

Crystal data

[Ag₂(C₁₁H₁₁N₃)₂](ClO₄)₂·2C₂H₆OS
M_r = 941.35
Monoclinic, P 2₁ /c
a = 7.3620 (3) Å
b = 11.1227 (5) Å
c = 21.1248 (10) Å
β = 95.328 (1)°
V = 1722.34 (13) Å³
Z = 2
Mo Kα radiation
μ = 1.48 mm⁻¹
T = 173 K
0.45 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
9537 measured reflections
3367 independent reflections
3096 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.02
3367 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2/C7–C11 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.88	2.32	3.081 (4)	144
C1—H1⋯O2ⁱ	0.95	2.56	3.214 (4)	126
C6—H6A⋯O5ⁱⁱ	0.99	2.55	3.495 (4)	160
C11—H11⋯O5ⁱⁱⁱ	0.95	2.55	3.191 (4)	125
C12—H12C⋯O4^iv	0.98	2.49	3.270 (5)	137
C13—H13A⋯Cg	0.98	3.36	4.116 (5)	136
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 963329

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026585/sj5353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026585/sj5353Isup2.hkl

checkCIF report

Comment top

In the development of silver(I) coordination polymers with fascinating structures, numerous symmetrical dipyridyl ligands with nitrogen donor atoms in the same positions on the two terminal pyridines are employed due to their easy synthesis (Lee et al., 2012; Leong & Vittal, 2011; Park et al., 2010). Despite the rapid growth in the Ag^I coordination chemistry, however, the investigation of Ag^I coordination polymers using unsymmetrical dipyridyl ligands with nitrogen donor atoms on different positions in the two terminal pyridines still remains lacking (Moon et al., 2013; Zhang et al., 2013). Herein, we report the crystal structure of the title compound prepared by the reaction of silver(I) perchlorate with the unsymmetrical dipyridyl ligand N-(pyridine-3-ylmethyl)pyridine-2-amine. This was synthesized by the reaction of 2-aminopyridine and 3-pyridinecarboxaldehyde according to literature procedures (Foxon et al., 2002; Lee et al., 2008).

The binuclear cation of the title compound, [Ag₂(C₁₁H₁₁N₃)₂](ClO₄)₂(C₂H₆SO)₂, is located on an inversion centre. Therefore, the asymmetric unit of the compound consists of an Ag^I cation, an N-(pyridine-3-ylmethyl)pyridine-2-amine ligand, a perchlorate anion and a molecule of dimethyl sulfoxide (DMSO) solvent. The two Ag^I centres, each in a geometry slightly distorted from linear [N–Ag–N 170.78 (9)°], are coordinated by two pyridine N atoms from the two symmetry-related N-(pyridine-3-ylmethyl)pyridine-2-amine ligands, leading to the formation of a centrosymmetric 16-membered cyclic dimer (Fig. 1). The two pyridine rings coordinated to each Ag^I centre are almost perpendicular to each other [dihedral angle = 87.73 (10)°]. Moreover, each Ag^I centre in the cyclic dimer interacts weakly with the N atom of a secondary amine group [Ag1···N3 2.699 (3) Å] and the O atom of a DMSO solvent molecule and a ClO₄^- anion [Ag1···O5 2.686 (3) Å and Ag1···O2 3.149 (3) Å] (Fig. 1).

In the crystal structure, the cyclic units interact with the ClO₄^- anions and the DMSO solvent molecules via intermolecular N–H···O and C–H···O hydrogen-bonds and C–H···π interactions (Table 1, Fig. 1). These interactions lead to the construction of a three-dimensional supramolecular network (Fig. 2).

Related literature top

For structures of Ag^I coordination polymers with symmetrical dipyridyl ligands, see: Lee et al. (2012); Leong & Vittal (2011); Park et al. (2010) and of Ag^I coordination polymers with unsymmetrical dipyridyl ligands, see: Moon et al. (2013); Zhang et al. (2013). For the synthesis of the ligand, see: Foxon et al. (2002); Lee et al. (2008).

Experimental top

The ligand (N-(pyridin-3-ylmethyl)pyridine-2-amine) was prepared according to a procedure described by Foxon et al. (2002) and Lee et al. (2008). Crystals of the title compound suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into a DMSO solution of the white precipitate afforded by the reaction of the ligand with silver(I) perchlorate in the malar ratio 1:1 in methanol.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Intermolecular Ag···O interactions, N–H···O hydrogen bonds and C–H···π interactions are shown as yellow, black and red dashed lines, respectively. [Symmetry code: (i) 1 - x, - y, 1 - z].
	Fig. 2. The three-dimensional supramolecular structure formed through intermolecular Ag···O (yellow dashed lines) and C–H···O interactions (black dashed lines).

Bis[µ-N-(pyridin-2-ylmethyl)pyridin-3-amine-κ²N:N']disilver(I) bis(perchlorate) dimethyl sulfoxide disolvate top

Crystal data top

[Ag₂(C₁₁H₁₁N₃)₂](ClO₄)₂·2C₂H₆OS	F(000) = 944
M_r = 941.35	D_x = 1.815 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7360 reflections
a = 7.3620 (3) Å	θ = 2.7–28.3°
b = 11.1227 (5) Å	µ = 1.48 mm⁻¹
c = 21.1248 (10) Å	T = 173 K
β = 95.328 (1)°	Block, colorless
V = 1722.34 (13) Å³	0.45 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3096 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ϕ and ω scans	h = −9→8
9537 measured reflections	k = −13→13
3367 independent reflections	l = −25→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0399P)² + 3.5438P] where P = (F_o² + 2F_c²)/3
3367 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Ag₂(C₁₁H₁₁N₃)₂](ClO₄)₂·2C₂H₆OS	V = 1722.34 (13) Å³
M_r = 941.35	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3620 (3) Å	µ = 1.48 mm⁻¹
b = 11.1227 (5) Å	T = 173 K
c = 21.1248 (10) Å	0.45 × 0.20 × 0.20 mm
β = 95.328 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3096 reflections with I > 2σ(I)
9537 measured reflections	R_int = 0.049
3367 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.02	Δρ_max = 0.61 e Å⁻³
3367 reflections	Δρ_min = −0.65 e Å⁻³
217 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
Ag1	0.50109 (3)	0.25805 (2)	0.484406 (11)	0.02344 (10)
N1	0.3332 (3)	0.3841 (2)	0.53484 (12)	0.0200 (5)
N2	0.3266 (3)	−0.1183 (2)	0.55086 (12)	0.0200 (5)
N3	0.1611 (3)	0.1670 (2)	0.48358 (12)	0.0224 (5)
H3	0.2056	0.1604	0.4465	0.027*
C1	0.4183 (4)	0.4681 (3)	0.57264 (14)	0.0229 (6)
H1	0.5437	0.4832	0.5686	0.028*
C2	0.3334 (4)	0.5334 (3)	0.61688 (15)	0.0269 (7)
H2	0.3984	0.5924	0.6424	0.032*
C3	0.1510 (5)	0.5108 (3)	0.62316 (16)	0.0305 (7)
H3A	0.0886	0.5533	0.6536	0.037*
C4	0.0616 (4)	0.4257 (3)	0.58450 (17)	0.0288 (7)
H4	−0.0639	0.4096	0.5879	0.035*
C5	0.1546 (4)	0.3632 (3)	0.54062 (14)	0.0201 (6)
C6	0.0546 (4)	0.2732 (3)	0.49703 (16)	0.0240 (6)
H6A	−0.0562	0.2469	0.5164	0.029*
H6B	0.0145	0.3135	0.4563	0.029*
C7	0.1930 (4)	0.0766 (3)	0.52826 (14)	0.0186 (6)
C8	0.1501 (4)	0.0853 (3)	0.59090 (15)	0.0231 (6)
H8	0.0907	0.1548	0.6051	0.028*
C9	0.1955 (5)	−0.0089 (3)	0.63220 (15)	0.0275 (7)
H9	0.1657	−0.0049	0.6750	0.033*
C10	0.2841 (4)	−0.1091 (3)	0.61127 (15)	0.0265 (7)
H10	0.3156	−0.1727	0.6402	0.032*
C11	0.2807 (4)	−0.0285 (3)	0.51076 (14)	0.0187 (6)
H11	0.3090	−0.0362	0.4680	0.022*
Cl1	0.22314 (10)	0.27926 (7)	0.31521 (4)	0.02713 (18)
O1	0.1356 (6)	0.1764 (3)	0.33725 (17)	0.0789 (13)
O2	0.2542 (4)	0.3637 (3)	0.36785 (14)	0.0448 (7)
O3	0.1082 (5)	0.3355 (4)	0.26650 (16)	0.0698 (10)
O4	0.3925 (5)	0.2503 (3)	0.2927 (2)	0.0716 (12)
S1	0.60059 (11)	0.23249 (7)	0.65444 (4)	0.02617 (18)
O5	0.7044 (3)	0.2308 (2)	0.59577 (12)	0.0329 (5)
C12	0.7185 (5)	0.3371 (3)	0.70810 (17)	0.0378 (8)
H12A	0.6999	0.4189	0.6915	0.045*
H12B	0.8491	0.3184	0.7123	0.045*
H12C	0.6709	0.3312	0.7498	0.045*
C13	0.6627 (6)	0.0977 (4)	0.6968 (2)	0.0435 (9)
H13A	0.6077	0.0285	0.6736	0.052*
H13B	0.6187	0.1013	0.7392	0.052*
H13C	0.7958	0.0893	0.7011	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02007 (14)	0.02377 (15)	0.02746 (16)	0.00319 (8)	0.00743 (10)	−0.00257 (9)
N1	0.0173 (12)	0.0213 (12)	0.0218 (13)	0.0015 (9)	0.0038 (9)	0.0011 (10)
N2	0.0171 (12)	0.0227 (12)	0.0201 (12)	0.0000 (9)	0.0017 (9)	−0.0040 (10)
N3	0.0251 (13)	0.0213 (13)	0.0214 (13)	0.0007 (10)	0.0055 (10)	−0.0009 (10)
C1	0.0199 (14)	0.0255 (15)	0.0236 (15)	−0.0021 (12)	0.0026 (11)	0.0025 (12)
C2	0.0298 (17)	0.0243 (15)	0.0261 (16)	0.0005 (13)	0.0006 (13)	−0.0054 (13)
C3	0.0281 (17)	0.0325 (18)	0.0313 (17)	0.0059 (13)	0.0056 (13)	−0.0069 (14)
C4	0.0165 (14)	0.0332 (17)	0.0375 (18)	0.0030 (12)	0.0069 (13)	−0.0017 (15)
C5	0.0169 (13)	0.0212 (14)	0.0221 (15)	0.0008 (11)	0.0013 (11)	0.0061 (12)
C6	0.0170 (14)	0.0236 (15)	0.0310 (17)	0.0014 (11)	0.0010 (12)	−0.0006 (13)
C7	0.0134 (13)	0.0206 (14)	0.0216 (14)	−0.0032 (10)	0.0004 (10)	−0.0035 (11)
C8	0.0237 (15)	0.0227 (15)	0.0237 (15)	−0.0005 (12)	0.0064 (12)	−0.0050 (12)
C9	0.0332 (18)	0.0316 (17)	0.0187 (14)	0.0039 (13)	0.0077 (12)	−0.0018 (13)
C10	0.0292 (16)	0.0281 (16)	0.0221 (15)	0.0026 (13)	0.0016 (12)	0.0026 (13)
C11	0.0145 (13)	0.0238 (14)	0.0183 (14)	−0.0020 (11)	0.0041 (10)	−0.0031 (11)
Cl1	0.0197 (4)	0.0316 (4)	0.0305 (4)	−0.0007 (3)	0.0042 (3)	0.0034 (3)
O1	0.127 (3)	0.064 (2)	0.0482 (19)	−0.056 (2)	0.023 (2)	−0.0070 (17)
O2	0.0408 (15)	0.0491 (16)	0.0449 (16)	−0.0090 (12)	0.0067 (12)	−0.0133 (13)
O3	0.067 (2)	0.082 (3)	0.055 (2)	0.0250 (19)	−0.0210 (16)	0.0001 (18)
O4	0.0364 (18)	0.107 (3)	0.073 (3)	0.0121 (17)	0.0135 (17)	−0.029 (2)
S1	0.0257 (4)	0.0319 (4)	0.0210 (4)	0.0002 (3)	0.0030 (3)	−0.0023 (3)
O5	0.0330 (13)	0.0431 (14)	0.0235 (12)	0.0003 (10)	0.0071 (10)	−0.0045 (10)
C12	0.046 (2)	0.041 (2)	0.0263 (17)	−0.0081 (17)	0.0023 (15)	−0.0101 (15)
C13	0.051 (2)	0.036 (2)	0.043 (2)	−0.0006 (17)	0.0024 (18)	0.0077 (17)

Geometric parameters (Å, º) top

Ag1—N2ⁱ	2.181 (2)	C7—C8	1.392 (4)
Ag1—N1	2.208 (2)	C7—C11	1.402 (4)
N1—C1	1.345 (4)	C8—C9	1.385 (4)
N1—C5	1.352 (4)	C8—H8	0.9500
N2—C11	1.332 (4)	C9—C10	1.384 (4)
N2—C10	1.346 (4)	C9—H9	0.9500
N2—Ag1ⁱ	2.181 (2)	C10—H10	0.9500
N3—C7	1.384 (4)	C11—H11	0.9500
N3—C6	1.460 (4)	Cl1—O4	1.412 (3)
N3—H3	0.8800	Cl1—O1	1.413 (3)
C1—C2	1.379 (4)	Cl1—O3	1.416 (3)
C1—H1	0.9500	Cl1—O2	1.457 (3)
C2—C3	1.385 (5)	S1—O5	1.515 (3)
C2—H2	0.9500	S1—C13	1.784 (4)
C3—C4	1.377 (5)	S1—C12	1.791 (4)
C3—H3A	0.9500	C12—H12A	0.9800
C4—C5	1.389 (4)	C12—H12B	0.9800
C4—H4	0.9500	C12—H12C	0.9800
C5—C6	1.506 (4)	C13—H13A	0.9800
C6—H6A	0.9900	C13—H13B	0.9800
C6—H6B	0.9900	C13—H13C	0.9800

N2ⁱ—Ag1—N1	170.78 (9)	C9—C8—C7	118.9 (3)
C1—N1—C5	118.0 (3)	C9—C8—H8	120.5
C1—N1—Ag1	118.47 (19)	C7—C8—H8	120.5
C5—N1—Ag1	121.8 (2)	C10—C9—C8	120.1 (3)
C11—N2—C10	118.6 (3)	C10—C9—H9	120.0
C11—N2—Ag1ⁱ	115.99 (18)	C8—C9—H9	120.0
C10—N2—Ag1ⁱ	124.9 (2)	N2—C10—C9	121.5 (3)
C7—N3—C6	121.0 (3)	N2—C10—H10	119.3
C7—N3—H3	119.5	C9—C10—H10	119.3
C6—N3—H3	119.5	N2—C11—C7	123.6 (3)
N1—C1—C2	123.6 (3)	N2—C11—H11	118.2
N1—C1—H1	118.2	C7—C11—H11	118.2
C2—C1—H1	118.2	O4—Cl1—O1	111.7 (3)
C1—C2—C3	118.3 (3)	O4—Cl1—O3	110.0 (3)
C1—C2—H2	120.8	O1—Cl1—O3	109.7 (3)
C3—C2—H2	120.8	O4—Cl1—O2	108.8 (2)
C4—C3—C2	118.8 (3)	O1—Cl1—O2	108.34 (19)
C4—C3—H3A	120.6	O3—Cl1—O2	108.1 (2)
C2—C3—H3A	120.6	O5—S1—C13	105.98 (17)
C3—C4—C5	120.1 (3)	O5—S1—C12	105.90 (16)
C3—C4—H4	119.9	C13—S1—C12	98.13 (19)
C5—C4—H4	119.9	S1—C12—H12A	109.5
N1—C5—C4	121.2 (3)	S1—C12—H12B	109.5
N1—C5—C6	119.0 (3)	H12A—C12—H12B	109.5
C4—C5—C6	119.8 (3)	S1—C12—H12C	109.5
N3—C6—C5	114.6 (2)	H12A—C12—H12C	109.5
N3—C6—H6A	108.6	H12B—C12—H12C	109.5
C5—C6—H6A	108.6	S1—C13—H13A	109.5
N3—C6—H6B	108.6	S1—C13—H13B	109.5
C5—C6—H6B	108.6	H13A—C13—H13B	109.5
H6A—C6—H6B	107.6	S1—C13—H13C	109.5
N3—C7—C8	124.0 (3)	H13A—C13—H13C	109.5
N3—C7—C11	118.6 (3)	H13B—C13—H13C	109.5
C8—C7—C11	117.3 (3)

C5—N1—C1—C2	0.2 (4)	C4—C5—C6—N3	−143.6 (3)
Ag1—N1—C1—C2	−165.1 (2)	C6—N3—C7—C8	−9.0 (4)
N1—C1—C2—C3	0.5 (5)	C6—N3—C7—C11	173.9 (3)
C1—C2—C3—C4	−0.9 (5)	N3—C7—C8—C9	−177.2 (3)
C2—C3—C4—C5	0.7 (5)	C11—C7—C8—C9	0.0 (4)
C1—N1—C5—C4	−0.4 (4)	C7—C8—C9—C10	0.8 (5)
Ag1—N1—C5—C4	164.3 (2)	C11—N2—C10—C9	−0.3 (4)
C1—N1—C5—C6	177.6 (3)	Ag1ⁱ—N2—C10—C9	170.8 (2)
Ag1—N1—C5—C6	−17.7 (4)	C8—C9—C10—N2	−0.7 (5)
C3—C4—C5—N1	0.0 (5)	C10—N2—C11—C7	1.2 (4)
C3—C4—C5—C6	−178.0 (3)	Ag1ⁱ—N2—C11—C7	−170.7 (2)
C7—N3—C6—C5	75.8 (3)	N3—C7—C11—N2	176.4 (3)
N1—C5—C6—N3	38.4 (4)	C8—C7—C11—N2	−1.0 (4)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N2/C7–C11 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88	2.32	3.081 (4)	144
C1—H1···O2ⁱⁱ	0.95	2.56	3.214 (4)	126
C6—H6A···O5ⁱⁱⁱ	0.99	2.55	3.495 (4)	160
C11—H11···O5ⁱ	0.95	2.55	3.191 (4)	125
C12—H12C···O4^iv	0.98	2.49	3.270 (5)	137
C13—H13A···Cg	0.98	3.36	4.116 (5)	136

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N2/C7–C11 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88	2.32	3.081 (4)	144
C1—H1···O2ⁱ	0.95	2.56	3.214 (4)	126
C6—H6A···O5ⁱⁱ	0.99	2.55	3.495 (4)	160
C11—H11···O5ⁱⁱⁱ	0.95	2.55	3.191 (4)	125
C12—H12C···O4^iv	0.98	2.49	3.270 (5)	137
C13—H13A···Cg	0.98	3.36	4.116 (5)	136

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

Acknowledgements

This work was supported by NRF (2010–0022675) projects.

References

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Volume 69| Part 11| November 2013| Pages m575-m576

doi:10.1107/S1600536813026585

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