Propane-1,3-diaminium pyridine-2,5-di-carboxyl-ate dimethyl sulfoxide mono-solvate.

In the crystal structure of the title solvated molecular salt, C(3)H(12)N(2) (2+)·C(7)H(3)NO(4) (2-)·C(2)H(6)OS, two amine groups of propane-1,3-diamine (pda) are protonated and two carb-oxy-lic acid groups of pyridine-2,5-dicarb-oxy-lic acid (2,5-pydcH(2)) are deprotonated. The crystal packing features N-H⋯O hydrogen bonds and weak C-H⋯O inter-molecular inter-actions.

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

C3H12N2 2+·C7H3NO4 2−·C2H6OS

M = 319.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.095

S = 1.07

4010 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.34 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004545/jj2074sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H12N22+·C7H3NO42−·C2H6OS	F(000) = 680
Mr = 319.39	Dx = 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

STOE IPDS 2T diffractometer	3380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 29.2°, θmin = 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 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(Fo2) + (0.0447P)2 + 0.6814P] where P = (Fo2 + 2Fc2)/3
4010 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O1iv	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···O4v	0.86 (2)	1.96 (2)	2.7925 (17)	164.2 (18)
C8—H8A···O5vi	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

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⋯O1iv	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⋯O4v	0.86 (2)	1.96 (2)	2.7925 (17)	164.2 (18)
C8—H8A⋯O5vi	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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .