Bis(N,N′,N′′-triisopropyl­guanidinium) fumarate–fumaric acid (1/1)

Said, F.F.; Ali, B.F.; Richeson, D.; Korobkov, I.

doi:10.1107/S1600536812023094

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1906

doi:10.1107/S1600536812023094

Open

access

Bis(N,N′,N′′-triisopropylguanidinium) fumarate–fumaric acid (1/1)

Farouq F. Said,^a ^* Basem F. Ali,^a ^* Darrin Richeson ^b and Ilia Korobkov ^b

^aDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan, and ^bDepartment of Chemistry and Biochemistry, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5
^*Correspondence e-mail: fjuqqa@aabu.edu.jo, bfali@aabu.edu.jo

(Received 24 April 2012; accepted 20 May 2012; online 26 May 2012)

The asymmetric unit of the title compound, C₁₀H₂₄N₃⁺·0.5C₄H₂O₄²⁻·0.5C₄H₄O₄, comprises a triisopropylguanidinium cation, half of a fumarate dianion and half of a fumaric acid molecule; both the fumarate dianion and the fumaric acid molecule are located on inversion centres. In the crystal, intermolecular O—H⋯O hydrogen bonds between the carboxyl groups of the fumaric acid molecules and the carboxylate groups of the fumarate anions lead to the formation of a hydrogen-bonded supramolecular twisted chain along the b axis. The triisopropylguanidinium cations interact with the fumarate–fumaric acid chains via extensive N—H⋯O and C—H⋯O hydrogen bonds, leading to a ladder arrangement, with the cation being the rungs that bridge three curled chains of fumarate–fumaric acid. The crystal packing is stabilized by N—H⋯O and C—H⋯O (cation⋯fumarate/fumaric) and O—H⋯O (fumarate⋯fumaric) hydrogen bonds, consolidating a three-dimensional network.

Related literature

For background information and N,N′,N"-trisubstituted guanidinium salts, see: Said et al. (2011 ). For related structures, see: Said et al. (2005 ); Hemamalini & Fun (2010 ); Büyükgüngör et al. (2004 ). For the preparation of the triisopropyl guanidine compound, see: Ong et al. (2003 ).

Experimental

Crystal data

C₁₀H₂₄N₃⁺·0.5C₄H₂O₄²⁻·0.5C₄H₄O₄
M_r = 301.39
Monoclinic, P 2₁ /n
a = 9.714 (3) Å
b = 11.633 (3) Å
c = 16.226 (4) Å
β = 102.291 (4)°
V = 1791.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 200 K
0.50 × 0.45 × 0.45 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.960, T_max = 0.964
11184 measured reflections
2514 independent reflections
2121 reflections with I > 2σ(I)
R_int = 0.027
θ_max = 23.3°

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.04
2514 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.88	2.05	2.866 (2)	154
N2—H2A⋯O4ⁱ	0.88	2.22	2.976 (2)	144
N3—H3A⋯O1ⁱⁱ	0.88	2.04	2.866 (2)	155
O2—H2⋯O4ⁱⁱⁱ	0.84	1.66	2.484 (2)	168
C8—H8A⋯O3	1.00	2.49	3.356 (2)	144
C2—H2B⋯O4ⁱ	1.00	2.46	3.372 (2)	150
C5—H5A⋯O1ⁱⁱ	1.00	2.48	3.270 (2)	135
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023094/pv2540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023094/pv2540Isup2.hkl

checkCIF report

Comment top

In connection with ongoing studies of the structural aspects of N,N',N"-trisubstituted guanidinium salts (Said et al., 2011), we herein report the crystal structure of the title compound (Fig. 1). The bond distances and bond angles in the title compound agree very well with the corresponding bond distances and bond angles reported in a similar compound earlier (Said et al., 2005). The central guanidinium fragment of the cation is planar (sum of NCN angles is 360°). Both the fumarate and the fumaric acid units are planar and centrosymmetric with the inversion center at the midpoint of the C═C double bond. The C13—O3/O4 bonds in the fumarate dianion [1.222 (2) and 1.280 (2) Å] indicate a delocalized π-bonding arrangement as a consequence of deprotonation of the carboxylic acid group. On the other hand, the fumaric acid moiety displays a shorter C11—O1 bond [1.219 (3) Å] and a longer C11—O2 bond [1.302 (3) Å] as expected for a protonated carboxyl group. The carboxyl groups of the fumaric acid molecules and the carboxylate groups of the fumarate anions are hydrogen bonded through O2—H2···O4 leading to the formation of a one-dimensional hydrogen-bonded supramolecular twisting chain along the b -axis (Fig. 2, Table 1). This type of carboxyl-carboxylate interaction has been reported in the several crystal structures containing fumarate-fumaric acid species with different cations (Hemamalini & Fun, 2010, Büyükgüngör et al., 2004) indicating the stability of such a supramolecular motif. The triisopropyl guanidinium cations are bridging three fumarate-fumaric curled chains via extensive N—H···O hydrogen bonds (Table 1), forming triply bridged twisted chains, leading to a ladder type arrangement with guanidinium cation forming rungs (Fig. 2). The extensive hydrogen bonding interactions between the fumarate-fumaric acid chains and the ladder of guanidinium rungs along the b-axis consolidate the three-dimensional network.

Related literature top

For background information and N,N',N"-trisubstituted guanidinium salts, see: Said et al. (2011). For related structures, see: Said et al. (2005); Hemamalini & Fun (2010); Büyükgüngör et al. (2004). For the preparation of the triisopropyl guanidine compound, see: Ong et al. (2003).

Experimental top

N,N',N"-Triisopropylguanidine was prepared according to literature methods (Ong et al., 2003). In a round bottom flask, a mixture fumaric acid (0.395 mmol) and N,N',N"-triisopropylguanidine (0.395 mmol was dissolved in THF (10 ml). The reaction mixture was stirred, and a colorless precipitate formed over the next few minutes. The solid was removed by filtration and the product was crystallized from a mixture of THF:methanol (1:2) to give colorless crystals of the title compound (92% yield).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. Symmetry operations: (i) 2 -x,-y, 1 -z; (ii) -x, 1 -y, 1 -z.
	Fig. 2. A view of the hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

Bis(N,N',N''-triisopropylguanidinium) fumarate–fumaric acid (1/1) top

Crystal data top

C₁₀H₂₄N₃⁺·0.5C₄H₂O₄²⁻·0.5C₄H₄O₄	F(000) = 656
M_r = 301.39	D_x = 1.117 Mg m⁻³ D_m = n/a Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 309 reflections
a = 9.714 (3) Å	θ = 2.2–23.3°
b = 11.633 (3) Å	µ = 0.08 mm⁻¹
c = 16.226 (4) Å	T = 200 K
β = 102.291 (4)°	Block, colourless
V = 1791.6 (8) Å³	0.50 × 0.45 × 0.45 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2514 independent reflections
Radiation source: fine-focus sealed tube	2121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 23.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
T_min = 0.960, T_max = 0.964	k = −12→12
11184 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0727P)² + 0.7515P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2514 reflections	Δρ_max = 0.22 e Å⁻³
191 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Crystal data top

C₁₀H₂₄N₃⁺·0.5C₄H₂O₄²⁻·0.5C₄H₄O₄	V = 1791.6 (8) Å³
M_r = 301.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.714 (3) Å	µ = 0.08 mm⁻¹
b = 11.633 (3) Å	T = 200 K
c = 16.226 (4) Å	0.50 × 0.45 × 0.45 mm
β = 102.291 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2514 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2121 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.964	R_int = 0.027
11184 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
2514 reflections	Δρ_min = −0.18 e Å⁻³
191 parameters

Special details top

Experimental. Data collection is performed with three batch runs at phi = 0.00 ° (650 frames), at phi = 120.00 ° (650 frames), and at phi = 240.00 ° (650 frames). Frame width = 0.30 ° in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data.

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	0.3813 (2)	0.7589 (2)	0.65518 (12)	0.0606 (6)
H1A	0.3496	0.7206	0.6082	0.073*
N2	0.55340 (17)	0.87868 (16)	0.72883 (10)	0.0407 (5)
H2A	0.5134	0.8698	0.7722	0.049*
N3	0.55035 (18)	0.83370 (15)	0.58961 (10)	0.0400 (5)
H3A	0.6221	0.8809	0.5930	0.048*
C1	0.4961 (2)	0.82257 (18)	0.65809 (12)	0.0372 (5)
C2	0.3022 (3)	0.7462 (3)	0.72241 (15)	0.0618 (8)
H2B	0.3531	0.7879	0.7738	0.074*
C3	0.1559 (4)	0.7963 (3)	0.6947 (2)	0.0908 (10)
H3B	0.1630	0.8780	0.6813	0.136*
H3C	0.1047	0.7880	0.7402	0.136*
H3D	0.1053	0.7554	0.6445	0.136*
C4	0.2946 (4)	0.6209 (3)	0.7427 (2)	0.0980 (12)
H4A	0.3902	0.5903	0.7614	0.147*
H4B	0.2463	0.5794	0.6922	0.147*
H4C	0.2424	0.6111	0.7876	0.147*
C5	0.6772 (2)	0.95385 (17)	0.74056 (13)	0.0377 (5)
H5A	0.6841	0.9853	0.6842	0.045*
C6	0.6565 (3)	1.0533 (2)	0.79649 (16)	0.0575 (7)
H6A	0.5696	1.0942	0.7712	0.086*
H6B	0.7367	1.1061	0.8023	0.086*
H6C	0.6500	1.0243	0.8522	0.086*
C7	0.8100 (3)	0.8884 (2)	0.77559 (19)	0.0652 (7)
H7A	0.8199	0.8251	0.7374	0.098*
H7B	0.8056	0.8574	0.8311	0.098*
H7C	0.8911	0.9401	0.7811	0.098*
C8	0.5007 (2)	0.77405 (19)	0.50895 (13)	0.0438 (6)
H8A	0.3956	0.7697	0.4980	0.053*
C9	0.5406 (3)	0.8431 (2)	0.43942 (14)	0.0555 (6)
H9A	0.5003	0.9204	0.4387	0.083*
H9B	0.5041	0.8054	0.3852	0.083*
H9C	0.6434	0.8486	0.4490	0.083*
C10	0.5571 (4)	0.6538 (2)	0.51258 (18)	0.0841 (10)
H10A	0.5288	0.6120	0.5587	0.126*
H10B	0.6602	0.6561	0.5223	0.126*
H10C	0.5193	0.6147	0.4591	0.126*
C11	0.8673 (2)	0.02478 (18)	0.57016 (13)	0.0372 (5)
C12	0.9785 (2)	0.04210 (18)	0.52111 (13)	0.0366 (5)
H12A	1.0196	0.1161	0.5202	0.044*
C13	0.0836 (2)	0.63781 (18)	0.46512 (12)	0.0373 (5)
C14	−0.0139 (2)	0.54111 (18)	0.47181 (12)	0.0388 (5)
H14A	−0.1018	0.5388	0.4327	0.047*
O1	0.81517 (17)	−0.06979 (13)	0.57428 (11)	0.0534 (5)
O2	0.82763 (15)	0.11397 (12)	0.60762 (10)	0.0468 (4)
H2	0.8741	0.1718	0.5986	0.070*
O3	0.19305 (19)	0.64871 (16)	0.51791 (11)	0.0672 (6)
O4	0.04379 (15)	0.70345 (12)	0.40121 (9)	0.0425 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0536 (12)	0.0929 (16)	0.0369 (10)	−0.0418 (11)	0.0131 (9)	−0.0110 (10)
N2	0.0404 (10)	0.0532 (11)	0.0306 (9)	−0.0154 (8)	0.0123 (7)	−0.0032 (8)
N3	0.0414 (10)	0.0462 (10)	0.0337 (9)	−0.0158 (8)	0.0111 (7)	−0.0042 (8)
C1	0.0352 (11)	0.0435 (12)	0.0321 (11)	−0.0100 (9)	0.0058 (9)	0.0015 (9)
C2	0.0527 (14)	0.094 (2)	0.0402 (13)	−0.0384 (14)	0.0138 (11)	−0.0032 (13)
C3	0.093 (2)	0.087 (2)	0.106 (3)	0.0130 (18)	0.051 (2)	0.0107 (19)
C4	0.091 (2)	0.116 (3)	0.098 (2)	0.018 (2)	0.0448 (19)	0.059 (2)
C5	0.0373 (11)	0.0419 (12)	0.0344 (11)	−0.0107 (9)	0.0085 (9)	−0.0029 (9)
C6	0.0753 (17)	0.0488 (15)	0.0524 (14)	−0.0164 (12)	0.0227 (13)	−0.0100 (11)
C7	0.0413 (13)	0.0687 (17)	0.0832 (19)	−0.0008 (12)	0.0076 (13)	0.0107 (14)
C8	0.0505 (13)	0.0483 (13)	0.0303 (11)	−0.0115 (10)	0.0035 (9)	−0.0018 (9)
C9	0.0729 (16)	0.0591 (15)	0.0346 (12)	−0.0105 (12)	0.0115 (11)	−0.0006 (11)
C10	0.143 (3)	0.0518 (17)	0.0493 (16)	0.0038 (17)	0.0019 (17)	−0.0053 (12)
C11	0.0385 (11)	0.0384 (12)	0.0380 (11)	−0.0092 (9)	0.0154 (9)	−0.0038 (9)
C12	0.0381 (11)	0.0344 (11)	0.0404 (11)	−0.0115 (8)	0.0152 (9)	−0.0012 (8)
C13	0.0428 (12)	0.0405 (12)	0.0291 (11)	−0.0111 (9)	0.0089 (9)	−0.0064 (9)
C14	0.0378 (11)	0.0453 (12)	0.0313 (10)	−0.0120 (9)	0.0028 (9)	−0.0033 (8)
O1	0.0598 (10)	0.0442 (9)	0.0669 (11)	−0.0215 (8)	0.0376 (8)	−0.0112 (8)
O2	0.0534 (9)	0.0382 (8)	0.0578 (9)	−0.0073 (7)	0.0316 (8)	−0.0029 (7)
O3	0.0652 (11)	0.0750 (12)	0.0514 (10)	−0.0411 (9)	−0.0100 (9)	0.0121 (9)
O4	0.0539 (9)	0.0377 (8)	0.0366 (8)	−0.0069 (7)	0.0111 (7)	0.0000 (6)

Geometric parameters (Å, º) top

N1—C1	1.331 (3)	C7—H7A	0.9800
N1—C2	1.469 (3)	C7—H7B	0.9800
N1—H1A	0.8800	C7—H7C	0.9800
N2—C1	1.335 (3)	C8—C10	1.499 (4)
N2—C5	1.466 (3)	C8—C9	1.502 (3)
N2—H2A	0.8800	C8—H8A	1.0000
N3—C1	1.334 (3)	C9—H9A	0.9800
N3—C8	1.469 (3)	C9—H9B	0.9800
N3—H3A	0.8800	C9—H9C	0.9800
C2—C4	1.500 (5)	C10—H10A	0.9800
C2—C3	1.513 (4)	C10—H10B	0.9800
C2—H2B	1.0000	C10—H10C	0.9800
C3—H3B	0.9800	C11—O1	1.219 (2)
C3—H3C	0.9800	C11—O2	1.302 (3)
C3—H3D	0.9800	C11—C12	1.485 (3)
C4—H4A	0.9800	C12—C12ⁱ	1.314 (4)
C4—H4B	0.9800	C12—H12A	0.9500
C4—H4C	0.9800	C13—O3	1.222 (3)
C5—C7	1.501 (3)	C13—O4	1.279 (3)
C5—C6	1.510 (3)	C13—C14	1.489 (3)
C5—H5A	1.0000	C14—C14ⁱⁱ	1.311 (4)
C6—H6A	0.9800	C14—H14A	0.9500
C6—H6B	0.9800	O2—H2	0.8400
C6—H6C	0.9800

C1—N1—C2	126.59 (19)	H6A—C6—H6C	109.5
C1—N1—H1A	116.7	H6B—C6—H6C	109.5
C2—N1—H1A	116.7	C5—C7—H7A	109.5
C1—N2—C5	125.70 (16)	C5—C7—H7B	109.5
C1—N2—H2A	117.1	H7A—C7—H7B	109.5
C5—N2—H2A	117.1	C5—C7—H7C	109.5
C1—N3—C8	125.69 (17)	H7A—C7—H7C	109.5
C1—N3—H3A	117.2	H7B—C7—H7C	109.5
C8—N3—H3A	117.2	N3—C8—C10	110.97 (19)
N1—C1—N2	119.70 (18)	N3—C8—C9	109.17 (18)
N1—C1—N3	120.07 (18)	C10—C8—C9	112.2 (2)
N2—C1—N3	120.18 (17)	N3—C8—H8A	108.1
N1—C2—C4	108.6 (2)	C10—C8—H8A	108.1
N1—C2—C3	110.3 (2)	C9—C8—H8A	108.1
C4—C2—C3	110.6 (2)	C8—C9—H9A	109.5
N1—C2—H2B	109.1	C8—C9—H9B	109.5
C4—C2—H2B	109.1	H9A—C9—H9B	109.5
C3—C2—H2B	109.1	C8—C9—H9C	109.5
C2—C3—H3B	109.5	H9A—C9—H9C	109.5
C2—C3—H3C	109.5	H9B—C9—H9C	109.5
H3B—C3—H3C	109.5	C8—C10—H10A	109.5
C2—C3—H3D	109.5	C8—C10—H10B	109.5
H3B—C3—H3D	109.5	H10A—C10—H10B	109.5
H3C—C3—H3D	109.5	C8—C10—H10C	109.5
C2—C4—H4A	109.5	H10A—C10—H10C	109.5
C2—C4—H4B	109.5	H10B—C10—H10C	109.5
H4A—C4—H4B	109.5	O1—C11—O2	121.74 (18)
C2—C4—H4C	109.5	O1—C11—C12	120.65 (18)
H4A—C4—H4C	109.5	O2—C11—C12	117.61 (17)
H4B—C4—H4C	109.5	C12ⁱ—C12—C11	121.8 (2)
N2—C5—C7	111.20 (19)	C12ⁱ—C12—H12A	119.1
N2—C5—C6	108.94 (17)	C11—C12—H12A	119.1
C7—C5—C6	112.0 (2)	O3—C13—O4	125.02 (19)
N2—C5—H5A	108.2	O3—C13—C14	119.94 (19)
C7—C5—H5A	108.2	O4—C13—C14	115.03 (18)
C6—C5—H5A	108.2	C14ⁱⁱ—C14—C13	124.2 (2)
C5—C6—H6A	109.5	C14ⁱⁱ—C14—H14A	117.9
C5—C6—H6B	109.5	C13—C14—H14A	117.9
H6A—C6—H6B	109.5	C11—O2—H2	109.5
C5—C6—H6C	109.5

C2—N1—C1—N2	3.1 (4)	C1—N2—C5—C7	−92.6 (3)
C2—N1—C1—N3	−174.4 (2)	C1—N2—C5—C6	143.5 (2)
C5—N2—C1—N1	−178.4 (2)	C1—N3—C8—C10	−80.4 (3)
C5—N2—C1—N3	−1.0 (3)	C1—N3—C8—C9	155.4 (2)
C8—N3—C1—N1	−4.8 (3)	O1—C11—C12—C12ⁱ	1.9 (4)
C8—N3—C1—N2	177.8 (2)	O2—C11—C12—C12ⁱ	−177.6 (3)
C1—N1—C2—C4	−123.8 (3)	O3—C13—C14—C14ⁱⁱ	−5.4 (4)
C1—N1—C2—C3	114.8 (3)	O4—C13—C14—C14ⁱⁱ	173.6 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.88	2.05	2.866 (2)	154
N2—H2A···O4ⁱⁱⁱ	0.88	2.22	2.976 (2)	144
N3—H3A···O1^iv	0.88	2.04	2.866 (2)	155
O2—H2···O4^v	0.84	1.66	2.484 (2)	168
C8—H8A···O3	1.00	2.49	3.356 (2)	144
C2—H2B···O4ⁱⁱⁱ	1.00	2.46	3.372 (2)	150
C5—H5A···O1^iv	1.00	2.48	3.270 (2)	135

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

Experimental details

Crystal data
Chemical formula	C₁₀H₂₄N₃⁺·0.5C₄H₂O₄²⁻·0.5C₄H₄O₄
M_r	301.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	9.714 (3), 11.633 (3), 16.226 (4)
β (°)	102.291 (4)
V (Å³)	1791.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.45 × 0.45

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.960, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	11184, 2514, 2121
R_int	0.027
θ_max (°)	23.3
(sin θ/λ)_max (Å⁻¹)	0.556

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.04
No. of reflections	2514
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.88	2.05	2.866 (2)	153.5
N2—H2A···O4ⁱ	0.88	2.22	2.976 (2)	143.8
N3—H3A···O1ⁱⁱ	0.88	2.04	2.866 (2)	154.9
O2—H2···O4ⁱⁱⁱ	0.84	1.66	2.484 (2)	167.9
C8—H8A···O3	1.00	2.49	3.356 (2)	144.0
C2—H2B···O4ⁱ	1.00	2.46	3.372 (2)	150.3
C5—H5A···O1ⁱⁱ	1.00	2.48	3.270 (2)	134.9

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

Acknowledgements

The authors thank the Natural Sciences and Engineering Research Council (NSERC) of Canada and Al al-Bayt University (Jordan) for funding.

References

Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Büyükgüngör, O., Odabaşoğlu, M., Albayrak, Ç. & Lönnecke, P. (2004). Acta Cryst. C60, o470–o472. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2093–o2094. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ong, T. G., Yap, G. P. A. & Richeson, D. S. (2003). J. Am. Chem. Soc. 125, 8100–8101. Web of Science CSD CrossRef PubMed CAS Google Scholar
Said, F. F., Ali, B. F. & Richeson, D. (2011). Acta Cryst. E67, o3467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Said, F. F., Ong, T. G., Yap, G. P. A. & Richeson, D. (2005). Cryst. Growth Des. 5, 1881–1888. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar