Propane-1,3-diaminium pyridine-2,5-di­carboxyl­ate dimethyl sulfoxide mono­solvate

Aghabozorg, H.; Bayan, M.; Mirzaei, M.; Notash, B.

doi:10.1107/S1600536811004545

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o610

doi:10.1107/S1600536811004545

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Propane-1,3-diaminium pyridine-2,5-dicarboxylate dimethyl sulfoxide monosolvate

Hossein Aghabozorg,^a Minoo Bayan,^a ^* Masoud Mirzaei ^b and Behrouz Notash ^c

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran
^*Correspondence e-mail: minoobayan@yahoo.com

(Received 21 January 2011; accepted 7 February 2011; online 12 February 2011)

In the crystal structure of the title solvated molecular salt, C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₂H₆OS, two amine groups of propane-1,3-diamine (pda) are protonated and two carboxylic acid groups of pyridine-2,5-dicarboxylic acid (2,5-pydcH₂) are deprotonated. The crystal packing features N—H⋯O hydrogen bonds and weak C—H⋯O intermolecular interactions.

Related literature

Pyridine-2,5-dicarboxylic acid (2,5-pydcH₂) can coordinate to metal centers (Pasdar et al., 2011 ) or form hydrogen-bonded networks (Zeng et al., 2005 ). For work by our group on the synthesis of proton-transfer compounds containing different proton donor and acceptor groups, see: Eshtiagh-Hosseini et al. (2010a ,b ); Aghabozorg et al. (2008 , 2011 ).

Experimental

Crystal data

C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₂H₆OS
M_r = 319.39
Monoclinic, P 2₁ /n
a = 11.984 (2) Å
b = 10.346 (2) Å
c = 12.942 (3) Å
β = 111.63 (3)°
V = 1491.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 120 K
0.4 × 0.3 × 0.3 mm

Data collection

STOE IPDS 2T diffractometer
12249 measured reflections
4010 independent reflections
3380 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.095
S = 1.07
4010 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.91 (2)	1.96 (2)	2.8260 (16)	157.8 (17)
N2—H2B⋯O3ⁱⁱ	0.86 (2)	2.06 (2)	2.8461 (17)	151.0 (18)
N2—H2C⋯O2ⁱⁱⁱ	0.92 (2)	1.84 (2)	2.7385 (17)	164.4 (18)
N3—H3A⋯O1^iv	0.91 (2)	1.85 (2)	2.7369 (17)	161.6 (18)
N3—H3B⋯O3	0.890 (19)	2.073 (19)	2.8427 (16)	144.2 (16)
N3—H3C⋯O4^v	0.86 (2)	1.96 (2)	2.7925 (17)	164.2 (18)
C8—H8A⋯O5^vi	0.97	2.50	3.4614 (19)	170
C10—H10A⋯O5	0.97	2.53	3.4718 (19)	165
C11—H11B⋯O1ⁱⁱ	0.96	2.46	3.424 (2)	178
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z; (iv) x-1, y, z; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x, -y+2, -z.

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; 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/S1600536811004545/jj2074sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004545/jj2074Isup2.hkl

checkCIF report

Comment top

Pyridine-2,5-dicarboxylic acid (2,5-pydcH₂) can coordinate to metal centers (Pasdar et al., 2011) or form hydrogen-bonded networks (Zeng et al., 2005). Our research group has been focused on synthesis of proton transfer compounds containing different proton donor and acceptor groups (Eshtiagh-Hosseini et al., 2010a; Eshtiagh-Hosseini et al., 2010b; Aghabozorg et al., 2008, 2011).

We report here the synthesis and crystal structure of the title proton transfer compound, [pdaH2]²⁺.[2,5-pydc]^2-.(DMSO). The asymmetric unit contains deprotonated pyridine-2,5-dicarboxylic acid, diprotonated propane-1,3-diamine, and one DMSO solvent molecule (Fig. 1). Crystal packing is stabilized by N—H···O hydrogen bonds and weak C—H···O intermolecular interactions (Fig. 2 & Table 1).

Related literature top

Pyridine-2,5-dicarboxylic acid (2,5-pydcH₂) can coordinate to metal centers (Pasdar et al., 2011) or form hydrogen-bonded networks (Zeng et al., 2005). For work by our group on the synthesis of proton-transfer compounds containing different proton donor and acceptor groups, see: Eshtiagh-Hosseini et al. (2010a,b); Aghabozorg et al. (2008, 2011).

Experimental top

Propane-1,3-diamine (0.07 g, 0.29 ml, 1 mmol) was added to a DMSO/H₂O solution of pyridine-2,5-dicarboxylic acid (0.17 g, 1 mmol) (13 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were isolated by slow evaporation of the solvent after two months.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (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 title compound with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The packing diagram of the title compound, viewed down the a axis, showing N—H···O hydrogen bonds and weak C—H···O intermolecular interactions (dashed lines).

Propane-1,3-diaminium pyridine-2,5-dicarboxylate dimethyl sulfoxide monosolvate top

Crystal data top

C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₂H₆OS	F(000) = 680
M_r = 319.39	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4010 reflections
a = 11.984 (2) Å	θ = 2.6–29.2°
b = 10.346 (2) Å	µ = 0.24 mm⁻¹
c = 12.942 (3) Å	T = 120 K
β = 111.63 (3)°	Block, colorless
V = 1491.6 (6) Å³	0.4 × 0.3 × 0.3 mm
Z = 4

Data collection top

STOE IPDS 2T diffractometer	3380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 29.2°, θ_min = 2.6°
Detector resolution: 0.15 pixels mm^-1	h = −16→14
rotation method scans	k = −14→14
12249 measured reflections	l = −17→17
4010 independent 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0447P)² + 0.6814P] where P = (F_o² + 2F_c²)/3
4010 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₂H₆OS	V = 1491.6 (6) Å³
M_r = 319.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.984 (2) Å	µ = 0.24 mm⁻¹
b = 10.346 (2) Å	T = 120 K
c = 12.942 (3) Å	0.4 × 0.3 × 0.3 mm
β = 111.63 (3)°

Data collection top

STOE IPDS 2T diffractometer	3380 reflections with I > 2σ(I)
12249 measured reflections	R_int = 0.035
4010 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.43 e Å⁻³
4010 reflections	Δρ_min = −0.34 e Å⁻³
216 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
S1	0.25330 (3)	0.98812 (3)	0.01042 (3)	0.01677 (10)
O1	0.89632 (10)	0.63514 (12)	0.26504 (10)	0.0237 (2)
O2	0.87767 (10)	0.45057 (12)	0.17030 (11)	0.0271 (3)
O3	0.28902 (9)	0.63320 (10)	0.16349 (8)	0.0147 (2)
O4	0.28589 (9)	0.41856 (10)	0.13819 (8)	0.0145 (2)
O5	0.26031 (11)	1.00924 (11)	0.12737 (9)	0.0216 (2)
N1	0.52969 (11)	0.63725 (11)	0.20599 (10)	0.0136 (2)
N2	−0.08584 (11)	0.67039 (12)	−0.18378 (10)	0.0120 (2)
H2A	−0.1484 (18)	0.6233 (18)	−0.1797 (15)	0.018 (5)*
H2B	−0.1114 (17)	0.7160 (19)	−0.2439 (16)	0.019 (5)*
H2C	−0.0253 (19)	0.619 (2)	−0.1876 (16)	0.024 (5)*
N3	0.09589 (11)	0.71239 (12)	0.22640 (10)	0.0122 (2)
H3A	0.0361 (18)	0.6692 (19)	0.2400 (15)	0.020 (5)*
H3B	0.1526 (17)	0.6583 (18)	0.2240 (14)	0.013 (4)*
H3C	0.1289 (18)	0.768 (2)	0.2777 (16)	0.021 (5)*
C1	0.83737 (12)	0.54143 (14)	0.20910 (12)	0.0143 (3)
C2	0.70396 (12)	0.53745 (13)	0.18810 (11)	0.0116 (2)
C3	0.63536 (13)	0.43090 (13)	0.13750 (12)	0.0151 (3)
H3	0.6694	0.3631	0.1122	0.018*
C4	0.51512 (13)	0.42656 (13)	0.12501 (12)	0.0144 (3)
H4	0.4682	0.3550	0.0929	0.017*
C5	0.46609 (11)	0.53089 (13)	0.16125 (11)	0.0108 (2)
C6	0.33590 (12)	0.52826 (13)	0.15352 (10)	0.0111 (2)
C7	0.64639 (12)	0.63845 (13)	0.21994 (11)	0.0133 (3)
H7	0.6915	0.7109	0.2528	0.016*
C8	−0.03989 (13)	0.75898 (13)	−0.08677 (11)	0.0144 (3)
H8A	−0.1022	0.8202	−0.0896	0.017*
H8B	0.0278	0.8073	−0.0907	0.017*
C9	−0.00090 (12)	0.68569 (13)	0.02247 (11)	0.0134 (3)
H9A	0.0622	0.6249	0.0264	0.016*
H9B	−0.0682	0.6374	0.0272	0.016*
C10	0.04461 (13)	0.78090 (13)	0.11828 (11)	0.0139 (3)
H10A	0.1056	0.8357	0.1084	0.017*
H10B	−0.0210	0.8357	0.1183	0.017*
C11	0.37246 (17)	0.88029 (16)	0.02034 (14)	0.0256 (3)
H11A	0.4460	0.9123	0.0744	0.038*
H11B	0.3803	0.8739	−0.0507	0.038*
H11C	0.3553	0.7965	0.0427	0.038*
C12	0.31441 (17)	1.13018 (16)	−0.02737 (15)	0.0264 (3)
H12A	0.2650	1.2033	−0.0275	0.040*
H12B	0.3167	1.1191	−0.1002	0.040*
H12C	0.3943	1.1444	0.0253	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01593 (17)	0.01708 (17)	0.01747 (17)	−0.00372 (13)	0.00635 (13)	−0.00230 (13)
O1	0.0141 (5)	0.0294 (6)	0.0311 (6)	−0.0076 (5)	0.0125 (5)	−0.0101 (5)
O2	0.0145 (5)	0.0236 (6)	0.0466 (7)	0.0026 (5)	0.0151 (5)	−0.0072 (5)
O3	0.0106 (4)	0.0155 (5)	0.0186 (5)	0.0014 (4)	0.0061 (4)	−0.0011 (4)
O4	0.0103 (4)	0.0146 (5)	0.0187 (5)	−0.0015 (4)	0.0054 (4)	0.0018 (4)
O5	0.0245 (6)	0.0222 (5)	0.0223 (5)	−0.0018 (4)	0.0137 (4)	−0.0039 (4)
N1	0.0118 (5)	0.0126 (5)	0.0174 (5)	0.0001 (4)	0.0065 (4)	−0.0009 (4)
N2	0.0098 (5)	0.0133 (5)	0.0133 (5)	−0.0003 (4)	0.0046 (4)	−0.0006 (4)
N3	0.0092 (5)	0.0134 (5)	0.0133 (5)	−0.0004 (5)	0.0035 (4)	0.0003 (4)
C1	0.0103 (6)	0.0176 (6)	0.0164 (6)	0.0004 (5)	0.0064 (5)	0.0038 (5)
C2	0.0099 (6)	0.0131 (6)	0.0131 (6)	0.0005 (5)	0.0057 (5)	0.0017 (5)
C3	0.0139 (6)	0.0126 (6)	0.0208 (6)	0.0015 (5)	0.0087 (5)	−0.0021 (5)
C4	0.0122 (6)	0.0118 (6)	0.0195 (6)	−0.0013 (5)	0.0063 (5)	−0.0021 (5)
C5	0.0085 (6)	0.0121 (6)	0.0124 (5)	0.0006 (5)	0.0044 (5)	0.0022 (5)
C6	0.0082 (6)	0.0152 (6)	0.0101 (5)	0.0001 (5)	0.0035 (4)	0.0008 (5)
C7	0.0116 (6)	0.0114 (6)	0.0172 (6)	−0.0021 (5)	0.0056 (5)	−0.0021 (5)
C8	0.0166 (7)	0.0125 (6)	0.0144 (6)	−0.0006 (5)	0.0059 (5)	−0.0008 (5)
C9	0.0121 (6)	0.0132 (6)	0.0145 (6)	−0.0004 (5)	0.0047 (5)	0.0000 (5)
C10	0.0149 (6)	0.0127 (6)	0.0137 (6)	0.0001 (5)	0.0049 (5)	0.0007 (5)
C11	0.0380 (10)	0.0197 (7)	0.0261 (8)	0.0078 (7)	0.0201 (7)	0.0009 (6)
C12	0.0351 (9)	0.0171 (7)	0.0315 (8)	−0.0015 (7)	0.0175 (7)	0.0028 (6)

Geometric parameters (Å, º) top

S1—O5	1.5007 (12)	C3—C4	1.3904 (19)
S1—C11	1.7791 (17)	C3—H3	0.9300
S1—C12	1.7888 (17)	C4—C5	1.3905 (18)
O1—C1	1.2594 (18)	C4—H4	0.9300
O2—C1	1.2442 (19)	C5—C6	1.5265 (18)
O3—C6	1.2508 (17)	C7—H7	0.9300
O4—C6	1.2645 (17)	C8—C9	1.5182 (19)
N1—C5	1.3423 (17)	C8—H8A	0.9700
N1—C7	1.3427 (18)	C8—H8B	0.9700
N2—C8	1.4866 (18)	C9—C10	1.5189 (19)
N2—H2A	0.91 (2)	C9—H9A	0.9700
N2—H2B	0.86 (2)	C9—H9B	0.9700
N2—H2C	0.92 (2)	C10—H10A	0.9700
N3—C10	1.4847 (18)	C10—H10B	0.9700
N3—H3A	0.91 (2)	C11—H11A	0.9600
N3—H3B	0.890 (19)	C11—H11B	0.9600
N3—H3C	0.86 (2)	C11—H11C	0.9600
C1—C2	1.5204 (19)	C12—H12A	0.9600
C2—C3	1.3867 (19)	C12—H12B	0.9600
C2—C7	1.3955 (18)	C12—H12C	0.9600

O5—S1—C11	105.87 (8)	N1—C7—C2	123.87 (13)
O5—S1—C12	106.25 (7)	N1—C7—H7	118.1
C11—S1—C12	97.83 (8)	C2—C7—H7	118.1
C5—N1—C7	117.60 (12)	N2—C8—C9	111.69 (11)
C8—N2—H2A	109.7 (12)	N2—C8—H8A	109.3
C8—N2—H2B	108.8 (13)	C9—C8—H8A	109.3
H2A—N2—H2B	108.5 (17)	N2—C8—H8B	109.3
C8—N2—H2C	110.5 (12)	C9—C8—H8B	109.3
H2A—N2—H2C	112.2 (17)	H8A—C8—H8B	107.9
H2B—N2—H2C	107.1 (17)	C8—C9—C10	109.33 (12)
C10—N3—H3A	109.5 (12)	C8—C9—H9A	109.8
C10—N3—H3B	108.8 (11)	C10—C9—H9A	109.8
H3A—N3—H3B	111.2 (17)	C8—C9—H9B	109.8
C10—N3—H3C	108.6 (13)	C10—C9—H9B	109.8
H3A—N3—H3C	110.5 (17)	H9A—C9—H9B	108.3
H3B—N3—H3C	108.1 (17)	N3—C10—C9	111.05 (11)
O2—C1—O1	126.50 (14)	N3—C10—H10A	109.4
O2—C1—C2	116.52 (13)	C9—C10—H10A	109.4
O1—C1—C2	116.98 (13)	N3—C10—H10B	109.4
C3—C2—C7	117.59 (12)	C9—C10—H10B	109.4
C3—C2—C1	120.48 (12)	H10A—C10—H10B	108.0
C7—C2—C1	121.92 (12)	S1—C11—H11A	109.5
C2—C3—C4	119.29 (13)	S1—C11—H11B	109.5
C2—C3—H3	120.4	H11A—C11—H11B	109.5
C4—C3—H3	120.4	S1—C11—H11C	109.5
C3—C4—C5	118.97 (13)	H11A—C11—H11C	109.5
C3—C4—H4	120.5	H11B—C11—H11C	109.5
C5—C4—H4	120.5	S1—C12—H12A	109.5
N1—C5—C4	122.59 (12)	S1—C12—H12B	109.5
N1—C5—C6	116.55 (11)	H12A—C12—H12B	109.5
C4—C5—C6	120.85 (12)	S1—C12—H12C	109.5
O3—C6—O4	126.18 (12)	H12A—C12—H12C	109.5
O3—C6—C5	117.70 (12)	H12B—C12—H12C	109.5
O4—C6—C5	116.11 (12)

O2—C1—C2—C3	6.0 (2)	C3—C4—C5—C6	−177.55 (12)
O1—C1—C2—C3	−173.18 (13)	N1—C5—C6—O3	16.67 (17)
O2—C1—C2—C7	−175.04 (14)	C4—C5—C6—O3	−164.35 (13)
O1—C1—C2—C7	5.8 (2)	N1—C5—C6—O4	−162.89 (12)
C7—C2—C3—C4	−2.7 (2)	C4—C5—C6—O4	16.09 (18)
C1—C2—C3—C4	176.36 (13)	C5—N1—C7—C2	1.7 (2)
C2—C3—C4—C5	1.6 (2)	C3—C2—C7—N1	1.1 (2)
C7—N1—C5—C4	−2.97 (19)	C1—C2—C7—N1	−177.95 (13)
C7—N1—C5—C6	175.99 (11)	N2—C8—C9—C10	−179.79 (11)
C3—C4—C5—N1	1.4 (2)	C8—C9—C10—N3	−173.86 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.91 (2)	1.96 (2)	2.8260 (16)	157.8 (17)
N2—H2B···O3ⁱⁱ	0.86 (2)	2.06 (2)	2.8461 (17)	151.0 (18)
N2—H2C···O2ⁱⁱⁱ	0.92 (2)	1.84 (2)	2.7385 (17)	164.4 (18)
N3—H3A···O1^iv	0.91 (2)	1.85 (2)	2.7369 (17)	161.6 (18)
N3—H3B···O3	0.890 (19)	2.073 (19)	2.8427 (16)	144.2 (16)
N3—H3C···O4^v	0.86 (2)	1.96 (2)	2.7925 (17)	164.2 (18)
C8—H8A···O5^vi	0.97	2.50	3.4614 (19)	170
C10—H10A···O5	0.97	2.53	3.4718 (19)	165
C11—H11B···O1ⁱⁱ	0.96	2.46	3.424 (2)	178

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₂H₆OS
M_r	319.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	11.984 (2), 10.346 (2), 12.942 (3)
β (°)	111.63 (3)
V (Å³)	1491.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.4 × 0.3 × 0.3

Data collection
Diffractometer	STOE IPDS 2T diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12249, 4010, 3380
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.095, 1.07
No. of reflections	4010
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.34

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.91 (2)	1.96 (2)	2.8260 (16)	157.8 (17)
N2—H2B···O3ⁱⁱ	0.86 (2)	2.06 (2)	2.8461 (17)	151.0 (18)
N2—H2C···O2ⁱⁱⁱ	0.92 (2)	1.84 (2)	2.7385 (17)	164.4 (18)
N3—H3A···O1^iv	0.91 (2)	1.85 (2)	2.7369 (17)	161.6 (18)
N3—H3B···O3	0.890 (19)	2.073 (19)	2.8427 (16)	144.2 (16)
N3—H3C···O4^v	0.86 (2)	1.96 (2)	2.7925 (17)	164.2 (18)
C8—H8A···O5^vi	0.97	2.50	3.4614 (19)	170
C10—H10A···O5	0.97	2.53	3.4718 (19)	165
C11—H11B···O1ⁱⁱ	0.96	2.46	3.424 (2)	178

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x, −y+2, −z.

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Aghabozorg, H., Saemi, M., Khazaei, Z., Amani, V. & Notash, B. (2011). Acta Cryst. E67, o292. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Eshtiagh-Hosseini, H., Hassanpoor, A., Canadillas-Delgado, L. & Mirzaei, M. (2010b). Acta Cryst. E66, o1368–o1369. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 67| Part 3| March 2011| Page o610

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Propane-1,3-diaminium pyridine-2,5-di­carboxyl­ate di­methyl sulfoxide mono­solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Propane-1,3-diaminium pyridine-2,5-dicarboxylate dimethyl sulfoxide monosolvate