2,2′-Azanediyl­diethanaminium pyridine-2,5-dicarboxyl­ate

Aghabozorg, H.; Saemi, M.; Khazaei, Z.; Amani, V.; Notash, B.

doi:10.1107/S1600536810054413

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o292

doi:10.1107/S1600536810054413

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2,2′-Azanediyldiethanaminium pyridine-2,5-dicarboxylate

Hossein Aghabozorg,^a ^* Maryam Saemi,^a Zeynab Khazaei,^a Vahid Amani ^b and Behrouz Notash ^b

^aFaculty of Chemistry, Tarbiat Moallem University, 15614 Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 23 December 2010; accepted 27 December 2010; online 8 January 2011)

The crystal structure of the title compound, C₄H₁₅N₃²⁺·C₇H₃NO₄²⁻, consists of diethylenetriaminium (2,2′-azanediyldiethanaminium) cations and pyridine-2,5-dicarboxylate anions, which are linked by N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds. C—H⋯π interactions are also observed. In the anion, the carboxylate groups are oriented at dihedral angles of 11.04 (15) and 6.31 (14)° with respect to the pyridine ring.

Related literature

For general background to proton-transfer compounds, see: Sheshmani et al. (2007 ); Aghabozorg et al. (2008a ,b ,c ); Derikvand et al. (2009 ).

Experimental

Crystal data

C₄H₁₅N₃²⁺·C₇H₃NO₄²⁻
M_r = 270.29
Monoclinic, P 2₁ /c
a = 10.485 (2) Å
b = 7.7016 (15) Å
c = 17.254 (4) Å
β = 106.67 (3)°
V = 1334.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.3 × 0.3 × 0.15 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2005 ) T_min = 0.967, T_max = 0.983
14267 measured reflections
3593 independent reflections
2523 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.184
S = 1.18
3593 reflections
200 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.96 (3)	2.56 (3)	3.254 (3)	130 (2)
N2—H2A⋯O4ⁱ	0.96 (3)	1.94 (3)	2.886 (3)	169 (3)
N2—H2B⋯O1	0.90 (3)	1.98 (3)	2.821 (4)	155 (3)
N2—H2C⋯O3ⁱⁱ	0.99 (4)	1.87 (4)	2.843 (3)	167 (3)
N3—H3A⋯O2ⁱⁱⁱ	0.97 (4)	2.38 (4)	3.223 (3)	145 (3)
N4—H4A⋯O2	0.95 (4)	1.91 (4)	2.807 (4)	158 (3)
N4—H4B⋯O4ⁱⁱ	0.94 (4)	1.92 (3)	2.840 (3)	167 (4)
N4—H4C⋯O2^iv	0.91 (4)	1.98 (4)	2.823 (4)	154 (4)
N4—H4C⋯N1^iv	0.91 (4)	2.57 (4)	3.253 (4)	133 (3)
C8—H8A⋯O1^v	0.97	2.49	3.218 (4)	132
C3—H3⋯Cgⁱ	0.93	2.83	3.588 (3)	139
C10—H10B⋯Cgⁱⁱⁱ	0.97	2.91	3.846 (3)	161
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+1, -y, -z; (iv) -x+1, -y+1, -z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054413/xu5129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054413/xu5129Isup2.hkl

checkCIF report

Comment top

Proton transfer is very important in physics, chemistry and biochemistry. In order to develop new types of proton transfer compounds and hydrogen bonding systems, our research group has already synthesized proton transfer compounds with different proton donors and acceptors (Sheshmani et al., 2007; Aghabozorg et al., 2008a; Aghabozorg et al., 2008b; Aghabozorg et al., 2008c; Derikvand et al., 2009). We herein report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The crystal structure shows that two protons from two carboxylic acid groups are transferred to two N atoms of the diethylenetriamine.

As can be seen from the packing diagram (Fig. 2), there are variety intera and intermolecular N—H···O, N—H···N and C—H···O hydrogen bonds (Table 1) in the crystal structure

Also, as shown in Fig. 3, there are C—H···π interactions between C10—H10B bond of diethylenetriaminium ion and pyridine ring and C3—H3 bond of pyridine-2,5-dicarboxylate ion and symmetry-related pyridine ring in the crystal structure [distance from centroid = 2.91 and 2.83 Å; angle = 161 and 139 ° and symmetry codes: 1 - x, -y, -z and 2 - x, -1/2 + y, 1/2 - z, respectively].

Intermolecular N—H···O, N—H···N and C—H···O hydrogen bonds and C—H···π interactions in this compound seem to be effective in the stabilization of the crystal structure, resulting in the formation of a three-dimensional supramolecular structure.

Related literature top

For general background to proton-transfer compounds, see: Sheshmani et al. (2007); Aghabozorg et al. (2008a,b,c); Derikvand et al. (2009).

Experimental top

Diethylenetriamine (0.28 g, 0.29 ml, 2.66 mmol) was added to a solution of pyridine-2,5-dicarboxylic acid (0.45 g, 2.66 mmol) in methanol (50 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion to a pale yellow solution in water. Suitable crystals were isolated after one week (yield; 0.55 g, 76.5%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The unit-cell packing diagram for the title molecule.
	Fig. 3. Intermolecular C—H···π interactions for the title molecule.

2,2'-Azanediyldiethanaminium pyridine-2,5-dicarboxylate top

Crystal data top

C₄H₁₅N₃²⁺·C₇H₃NO₄²⁻	F(000) = 576.0
M_r = 270.29	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3595 reflections
a = 10.485 (2) Å	θ = 2.5–29.2°
b = 7.7016 (15) Å	µ = 0.10 mm⁻¹
c = 17.254 (4) Å	T = 298 K
β = 106.67 (3)°	Block, yellow
V = 1334.7 (5) Å³	0.3 × 0.3 × 0.15 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	3593 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.5°
rotation method scans	h = −14→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2005)	k = −10→10
T_min = 0.967, T_max = 0.983	l = −23→23
14267 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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0436P)² + 0.9032P] where P = (F_o² + 2F_c²)/3
3593 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₄H₁₅N₃²⁺·C₇H₃NO₄²⁻	V = 1334.7 (5) Å³
M_r = 270.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.485 (2) Å	µ = 0.10 mm⁻¹
b = 7.7016 (15) Å	T = 298 K
c = 17.254 (4) Å	0.3 × 0.3 × 0.15 mm
β = 106.67 (3)°

Data collection top

Stoe IPDS II diffractometer	3593 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2005)	2523 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.983	R_int = 0.099
14267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	0 restraints
wR(F²) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.39 e Å⁻³
3593 reflections	Δρ_min = −0.28 e Å⁻³
200 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
O1	0.6009 (2)	0.1955 (4)	0.15541 (15)	0.0729 (8)
O2	0.60280 (19)	0.3262 (3)	0.04174 (12)	0.0548 (6)
O3	1.29302 (19)	0.1713 (3)	0.26621 (13)	0.0551 (6)
O4	1.28741 (19)	0.3736 (3)	0.17248 (12)	0.0509 (5)
N1	0.8735 (2)	0.3611 (3)	0.09555 (13)	0.0391 (5)
N2	0.4579 (2)	−0.0627 (3)	0.21118 (15)	0.0382 (5)
N3	0.2987 (2)	−0.0099 (3)	0.04917 (15)	0.0460 (6)
N4	0.3271 (3)	0.3560 (4)	0.01663 (16)	0.0443 (6)
C1	0.8097 (2)	0.2669 (3)	0.13871 (15)	0.0327 (5)
C2	0.8779 (3)	0.1723 (4)	0.20632 (17)	0.0436 (6)
H2	0.8315	0.1112	0.2361	0.052*
C3	1.0150 (3)	0.1698 (4)	0.22901 (16)	0.0422 (6)
H3	1.0619	0.1033	0.2729	0.051*
C4	1.0825 (2)	0.2672 (3)	0.18589 (15)	0.0341 (5)
C5	1.0069 (3)	0.3606 (3)	0.12018 (16)	0.0381 (6)
H5	1.0515	0.4273	0.0913	0.046*
C6	0.6586 (2)	0.2626 (3)	0.10991 (16)	0.0381 (6)
C7	1.2334 (3)	0.2704 (4)	0.21038 (16)	0.0401 (6)
C8	0.3824 (3)	−0.2064 (4)	0.16064 (19)	0.0496 (7)
H8A	0.3570	−0.2911	0.1951	0.059*
H8B	0.4386	−0.2640	0.1326	0.059*
C9	0.2599 (3)	−0.1373 (4)	0.09994 (18)	0.0475 (7)
H9A	0.2120	−0.2316	0.0669	0.057*
H9B	0.2015	−0.0841	0.1277	0.057*
C10	0.1898 (3)	0.0876 (4)	−0.00271 (17)	0.0474 (7)
H10A	0.1346	0.1334	0.0290	0.057*
H10B	0.1353	0.0113	−0.0437	0.057*
C11	0.2408 (3)	0.2359 (4)	−0.04313 (17)	0.0525 (8)
H11A	0.2909	0.1892	−0.0777	0.063*
H11B	0.1657	0.3001	−0.0770	0.063*
H2A	0.539 (3)	−0.100 (4)	0.249 (2)	0.058 (9)*
H2B	0.486 (3)	0.011 (4)	0.1790 (18)	0.044 (8)*
H2C	0.405 (4)	0.010 (5)	0.238 (2)	0.069 (10)*
H3A	0.352 (4)	−0.064 (5)	0.018 (2)	0.083 (12)*
H4A	0.417 (4)	0.320 (4)	0.032 (2)	0.059 (9)*
H4B	0.300 (4)	0.365 (5)	0.064 (2)	0.068 (11)*
H4C	0.322 (4)	0.463 (5)	−0.006 (2)	0.078 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0440 (12)	0.103 (2)	0.0698 (15)	−0.0193 (12)	0.0137 (11)	0.0258 (14)
O2	0.0361 (10)	0.0691 (14)	0.0538 (12)	0.0065 (10)	0.0041 (9)	0.0145 (11)
O3	0.0376 (10)	0.0646 (14)	0.0590 (13)	0.0127 (10)	0.0074 (9)	0.0041 (11)
O4	0.0381 (10)	0.0631 (13)	0.0544 (12)	−0.0137 (9)	0.0176 (9)	−0.0085 (10)
N1	0.0391 (11)	0.0379 (11)	0.0397 (11)	−0.0011 (9)	0.0103 (9)	0.0061 (9)
N2	0.0306 (11)	0.0380 (12)	0.0428 (12)	−0.0004 (9)	0.0055 (10)	0.0057 (10)
N3	0.0443 (13)	0.0444 (13)	0.0448 (13)	0.0052 (10)	0.0055 (10)	0.0025 (11)
N4	0.0377 (12)	0.0476 (14)	0.0454 (14)	0.0005 (11)	0.0084 (10)	0.0097 (11)
C1	0.0326 (11)	0.0284 (11)	0.0369 (12)	0.0018 (9)	0.0096 (10)	0.0012 (10)
C2	0.0364 (13)	0.0458 (15)	0.0480 (15)	−0.0022 (11)	0.0108 (11)	0.0151 (12)
C3	0.0366 (13)	0.0429 (14)	0.0450 (14)	0.0023 (11)	0.0083 (11)	0.0119 (12)
C4	0.0336 (12)	0.0303 (12)	0.0387 (13)	−0.0013 (10)	0.0108 (10)	−0.0055 (10)
C6	0.0323 (12)	0.0391 (13)	0.0414 (14)	−0.0006 (10)	0.0084 (10)	0.0004 (11)
C7	0.0333 (12)	0.0418 (14)	0.0446 (14)	−0.0002 (11)	0.0105 (11)	−0.0114 (12)
C8	0.0522 (17)	0.0348 (14)	0.0556 (17)	−0.0015 (12)	0.0056 (14)	0.0031 (12)
C9	0.0450 (15)	0.0411 (14)	0.0493 (15)	−0.0075 (12)	0.0021 (12)	−0.0018 (13)
C10	0.0462 (15)	0.0427 (15)	0.0451 (15)	0.0017 (12)	0.0000 (12)	−0.0072 (12)
C11	0.0604 (18)	0.0531 (17)	0.0379 (14)	0.0071 (15)	0.0040 (13)	0.0039 (13)
C5	0.0414 (13)	0.0343 (12)	0.0403 (13)	−0.0041 (11)	0.0146 (11)	0.0039 (11)

Geometric parameters (Å, º) top

O1—C6	1.233 (3)	C1—C6	1.519 (3)
O2—C6	1.253 (3)	C2—C3	1.378 (4)
O3—C7	1.248 (3)	C2—H2	0.9300
O4—C7	1.262 (3)	C3—C4	1.385 (4)
N1—C5	1.340 (3)	C3—H3	0.9300
N1—C1	1.347 (3)	C4—C5	1.384 (4)
N2—C8	1.489 (4)	C4—C7	1.516 (3)
N2—H2A	0.96 (3)	C8—C9	1.503 (4)
N2—H2B	0.90 (3)	C8—H8A	0.9700
N2—H2C	1.00 (4)	C8—H8B	0.9700
N3—C10	1.444 (4)	C9—H9A	0.9700
N3—C9	1.450 (4)	C9—H9B	0.9700
N3—H3A	0.98 (4)	C10—C11	1.514 (4)
N4—C11	1.484 (4)	C10—H10A	0.9700
N4—H4A	0.94 (4)	C10—H10B	0.9700
N4—H4B	0.95 (4)	C11—H11A	0.9700
N4—H4C	0.91 (4)	C11—H11B	0.9700
C1—C2	1.387 (3)	C5—H5	0.9300

C5—N1—C1	117.5 (2)	O3—C7—O4	125.9 (2)
C8—N2—H2A	113.6 (19)	O3—C7—C4	117.2 (2)
C8—N2—H2B	108.7 (19)	O4—C7—C4	117.0 (2)
H2A—N2—H2B	103 (3)	N2—C8—C9	110.5 (2)
C8—N2—H2C	115 (2)	N2—C8—H8A	109.6
H2A—N2—H2C	111 (3)	C9—C8—H8A	109.6
H2B—N2—H2C	105 (3)	N2—C8—H8B	109.6
C10—N3—C9	114.7 (2)	C9—C8—H8B	109.6
C10—N3—H3A	111 (2)	H8A—C8—H8B	108.1
C9—N3—H3A	111 (2)	N3—C9—C8	109.2 (2)
C11—N4—H4A	112 (2)	N3—C9—H9A	109.8
C11—N4—H4B	112 (2)	C8—C9—H9A	109.8
H4A—N4—H4B	107 (3)	N3—C9—H9B	109.8
C11—N4—H4C	108 (2)	C8—C9—H9B	109.8
H4A—N4—H4C	109 (3)	H9A—C9—H9B	108.3
H4B—N4—H4C	108 (3)	N3—C10—C11	110.9 (2)
N1—C1—C2	122.0 (2)	N3—C10—H10A	109.5
N1—C1—C6	117.9 (2)	C11—C10—H10A	109.5
C2—C1—C6	120.1 (2)	N3—C10—H10B	109.5
C3—C2—C1	119.4 (2)	C11—C10—H10B	109.5
C3—C2—H2	120.3	H10A—C10—H10B	108.0
C1—C2—H2	120.3	N4—C11—C10	112.1 (2)
C2—C3—C4	119.5 (2)	N4—C11—H11A	109.2
C2—C3—H3	120.3	C10—C11—H11A	109.2
C4—C3—H3	120.3	N4—C11—H11B	109.2
C5—C4—C3	117.4 (2)	C10—C11—H11B	109.2
C5—C4—C7	121.8 (2)	H11A—C11—H11B	107.9
C3—C4—C7	120.8 (2)	N1—C5—C4	124.2 (2)
O1—C6—O2	125.4 (2)	N1—C5—H5	117.9
O1—C6—C1	117.2 (2)	C4—C5—H5	117.9
O2—C6—C1	117.4 (2)

C5—N1—C1—C2	0.1 (4)	C5—C4—C7—O3	−174.3 (2)
C5—N1—C1—C6	−178.4 (2)	C3—C4—C7—O3	5.8 (4)
N1—C1—C2—C3	−2.0 (4)	C5—C4—C7—O4	5.8 (4)
C6—C1—C2—C3	176.4 (3)	C3—C4—C7—O4	−174.1 (2)
C1—C2—C3—C4	2.6 (4)	C10—N3—C9—C8	−170.1 (2)
C2—C3—C4—C5	−1.3 (4)	N2—C8—C9—N3	58.8 (3)
C2—C3—C4—C7	178.6 (3)	C9—N3—C10—C11	170.9 (2)
N1—C1—C6—O1	−170.7 (3)	N3—C10—C11—N4	−58.1 (3)
C2—C1—C6—O1	10.9 (4)	C1—N1—C5—C4	1.3 (4)
N1—C1—C6—O2	9.9 (4)	C3—C4—C5—N1	−0.7 (4)
C2—C1—C6—O2	−168.6 (3)	C7—C4—C5—N1	179.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.96 (3)	2.56 (3)	3.254 (3)	130 (2)
N2—H2A···O4ⁱ	0.96 (3)	1.94 (3)	2.886 (3)	169 (3)
N2—H2B···O1	0.90 (3)	1.98 (3)	2.821 (4)	155 (3)
N2—H2C···O3ⁱⁱ	0.99 (4)	1.87 (4)	2.843 (3)	167 (3)
N3—H3A···O2ⁱⁱⁱ	0.97 (4)	2.38 (4)	3.223 (3)	145 (3)
N4—H4A···O2	0.95 (4)	1.91 (4)	2.807 (4)	158 (3)
N4—H4B···O4ⁱⁱ	0.94 (4)	1.92 (3)	2.840 (3)	167 (4)
N4—H4C···O2^iv	0.91 (4)	1.98 (4)	2.823 (4)	154 (4)
N4—H4C···N1^iv	0.91 (4)	2.57 (4)	3.253 (4)	133 (3)
C8—H8A···O1^v	0.97	2.49	3.218 (4)	132
C3—H3···Cgⁱ	0.93	2.83	3.588 (3)	139
C10—H10B···Cgⁱⁱⁱ	0.97	2.91	3.846 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₄H₁₅N₃²⁺·C₇H₃NO₄²⁻
M_r	270.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.485 (2), 7.7016 (15), 17.254 (4)
β (°)	106.67 (3)
V (Å³)	1334.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.3 × 0.15

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.967, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14267, 3593, 2523
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.184, 1.18
No. of reflections	3593
No. of parameters	200
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.28

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED32 (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.96 (3)	2.56 (3)	3.254 (3)	130 (2)
N2—H2A···O4ⁱ	0.96 (3)	1.94 (3)	2.886 (3)	169 (3)
N2—H2B···O1	0.90 (3)	1.98 (3)	2.821 (4)	155 (3)
N2—H2C···O3ⁱⁱ	0.99 (4)	1.87 (4)	2.843 (3)	167 (3)
N3—H3A···O2ⁱⁱⁱ	0.97 (4)	2.38 (4)	3.223 (3)	145 (3)
N4—H4A···O2	0.95 (4)	1.91 (4)	2.807 (4)	158 (3)
N4—H4B···O4ⁱⁱ	0.94 (4)	1.92 (3)	2.840 (3)	167 (4)
N4—H4C···O2^iv	0.91 (4)	1.98 (4)	2.823 (4)	154 (4)
N4—H4C···N1^iv	0.91 (4)	2.57 (4)	3.253 (4)	133 (3)
C8—H8A···O1^v	0.9700	2.4900	3.218 (4)	132
C3—H3···Cgⁱ	0.93	2.83	3.588 (3)	139
C10—H10B···Cgⁱⁱⁱ	0.97	2.91	3.846 (3)	161

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

Acknowledgements

We are grateful to Tarbiat Moallem University for financial support.

References

Aghabozorg, H., Manteghi, F. & Ghadermazi, M. (2008a). Acta Cryst. E64, o230. Web of Science CSD CrossRef IUCr Journals Google Scholar
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