Propane-1,2-diaminium bis-(4-meth-oxy-benzoate).

The asymmetric unit of the title salt, C(3)H(12)N(2) (2+)·2C(8)H(7)O(3) (-), contains two 4-meth-oxy-benzoate anions and one propane-1,2-diaminium cation. All the amino H atoms of the cation are involved in N-H⋯O hydrogen bonds with the carboxyl-ate O atoms of the anions.

Related literature

For related amide-acid co-crystal compounds, see: Almarsson & Zaworotko (2004 ▶); Blagden et al. (2008 ▶); Vishweshwar et al. (2006 ▶); Kapildev et al. (2011 ▶); Schultheiss & Newman (2009 ▶).

Experimental

Crystal data

C3H12N2 2+·2C8H7O3 −

M = 378.42

Monoclinic,

a = 13.847 (3) Å

b = 11.296 (2) Å

c = 12.893 (3) Å

β = 92.38 (3)°

V = 2014.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

20478 measured reflections

4611 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.194

S = 1.03

4611 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023968/xu5245sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023968/xu5245Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023968/xu5245Isup3.cml

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

C3H12N22+·2C8H7O3−	F(000) = 808
Mr = 378.42	Dx = 1.247 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4611 reflections
a = 13.847 (3) Å	θ = 3.2–27.5°
b = 11.296 (2) Å	µ = 0.09 mm−1
c = 12.893 (3) Å	T = 298 K
β = 92.38 (3)°	Block, colorless
V = 2014.8 (7) Å3	0.30 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.116
graphite	θmax = 27.5°, θmin = 3.2°
Detector resolution: 13.6612 pixels mm-1	h = −17→17
CCD profile fitting scans	k = −14→14
20478 measured reflections	l = −16→16
4611 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.210P] where P = (Fo2 + 2Fc2)/3
4611 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.58273 (13)	0.11367 (16)	0.42325 (14)	0.0557 (5)
O4	1.40303 (14)	0.20038 (18)	1.12055 (15)	0.0653 (6)
O5	1.37392 (14)	0.05243 (18)	1.01087 (14)	0.0620 (6)
N1	0.50945 (15)	0.09975 (19)	0.62133 (15)	0.0498 (6)
H1A	0.4635	0.1562	0.6181	0.075*
H1B	0.5442	0.1111	0.5647	0.075*
H1C	0.4780	0.0300	0.6173	0.075*
C10	1.28462 (19)	0.2302 (2)	0.9837 (2)	0.0501 (7)
O2	0.67887 (14)	0.0757 (2)	0.29455 (15)	0.0690 (6)
N2	0.46696 (16)	−0.00178 (19)	0.83553 (16)	0.0512 (6)
H2A	0.4327	0.0114	0.8922	0.077*
H2B	0.5128	−0.0577	0.8457	0.077*
H2C	0.4235	−0.0264	0.7863	0.077*
C2	0.73928 (19)	0.2000 (2)	0.4300 (2)	0.0467 (7)
C1	0.6619 (2)	0.1256 (2)	0.3787 (2)	0.0477 (7)
C9	1.3588 (2)	0.1555 (3)	1.0418 (2)	0.0535 (7)
O3	0.95714 (15)	0.3848 (2)	0.59171 (17)	0.0752 (7)
C7	0.7231 (2)	0.2669 (2)	0.5179 (2)	0.0520 (7)
H7A	0.6613	0.2694	0.5432	0.062*
C18	0.57151 (19)	0.1152 (3)	0.7178 (2)	0.0536 (8)
H18A	0.6003	0.1942	0.7140	0.064*
O6	1.08060 (18)	0.4243 (2)	0.81081 (19)	0.0930 (8)
C6	0.7958 (2)	0.3295 (3)	0.5685 (2)	0.0584 (8)
H6A	0.7825	0.3749	0.6264	0.070*
C14	1.1855 (2)	0.4049 (3)	0.9672 (3)	0.0634 (8)
H14A	1.1651	0.4766	0.9943	0.076*
C3	0.8322 (2)	0.2004 (3)	0.3933 (2)	0.0578 (8)
H3A	0.8447	0.1583	0.3333	0.069*
C19	0.5112 (2)	0.1142 (2)	0.8128 (2)	0.0538 (7)
H19A	0.5516	0.1382	0.8723	0.065*
H19B	0.4601	0.1725	0.8034	0.065*
C4	0.9066 (2)	0.2618 (3)	0.4437 (2)	0.0621 (8)
H4A	0.9683	0.2608	0.4177	0.074*
C15	1.2534 (2)	0.3372 (3)	1.0210 (2)	0.0556 (8)
H15A	1.2790	0.3645	1.0844	0.067*
C11	1.2458 (2)	0.1912 (3)	0.8880 (2)	0.0610 (8)
H11A	1.2658	0.1192	0.8612	0.073*
C5	0.8888 (2)	0.3252 (3)	0.5335 (2)	0.0578 (8)
C13	1.1480 (2)	0.3652 (3)	0.8723 (3)	0.0643 (8)
C12	1.1784 (2)	0.2581 (3)	0.8329 (2)	0.0695 (9)
H12A	1.1532	0.2313	0.7691	0.083*
C8	1.0557 (2)	0.3755 (3)	0.5628 (3)	0.0838 (11)
H8A	1.0963	0.4209	0.6101	0.126*
H8B	1.0616	0.4054	0.4936	0.126*
H8C	1.0754	0.2940	0.5653	0.126*
C17	0.6536 (2)	0.0284 (3)	0.7205 (3)	0.0834 (11)
H17A	0.6934	0.0407	0.7823	0.125*
H17B	0.6915	0.0397	0.6606	0.125*
H17C	0.6284	−0.0508	0.7203	0.125*
C16	1.0508 (3)	0.5392 (4)	0.8406 (3)	0.1064 (14)
H16A	1.0038	0.5689	0.7902	0.160*
H16B	1.1057	0.5911	0.8443	0.160*
H16C	1.0227	0.5352	0.9073	0.160*

	U11	U22	U33	U12	U13	U23
O1	0.0547 (12)	0.0615 (13)	0.0513 (11)	−0.0116 (10)	0.0062 (10)	−0.0012 (9)
O4	0.0720 (14)	0.0648 (13)	0.0573 (12)	−0.0055 (11)	−0.0173 (10)	−0.0007 (11)
O5	0.0738 (14)	0.0605 (13)	0.0516 (12)	0.0096 (11)	0.0034 (10)	−0.0024 (11)
N1	0.0553 (14)	0.0550 (14)	0.0392 (12)	−0.0071 (11)	0.0029 (11)	−0.0012 (11)
C10	0.0513 (17)	0.0542 (18)	0.0448 (15)	−0.0003 (14)	0.0028 (13)	−0.0006 (14)
O2	0.0651 (14)	0.0942 (16)	0.0480 (12)	−0.0191 (11)	0.0073 (10)	−0.0194 (11)
N2	0.0559 (14)	0.0587 (15)	0.0387 (12)	−0.0003 (12)	−0.0003 (11)	−0.0010 (11)
C2	0.0501 (17)	0.0468 (16)	0.0430 (15)	−0.0013 (13)	−0.0011 (13)	0.0056 (13)
C1	0.0533 (18)	0.0490 (17)	0.0405 (16)	−0.0041 (14)	−0.0017 (14)	0.0079 (13)
C9	0.0532 (18)	0.066 (2)	0.0416 (16)	−0.0069 (16)	0.0064 (14)	0.0029 (15)
O3	0.0579 (14)	0.0904 (17)	0.0763 (15)	−0.0086 (12)	−0.0097 (11)	−0.0223 (13)
C7	0.0525 (17)	0.0523 (17)	0.0513 (16)	0.0005 (14)	0.0048 (14)	0.0006 (14)
C18	0.0538 (18)	0.0624 (19)	0.0442 (16)	−0.0064 (15)	−0.0028 (14)	0.0030 (14)
O6	0.0970 (18)	0.0944 (18)	0.0850 (17)	0.0279 (15)	−0.0254 (14)	0.0055 (14)
C6	0.061 (2)	0.0561 (18)	0.0574 (18)	0.0016 (15)	−0.0010 (16)	−0.0108 (15)
C14	0.059 (2)	0.0568 (19)	0.074 (2)	0.0010 (16)	0.0023 (17)	−0.0053 (17)
C3	0.0562 (19)	0.070 (2)	0.0472 (16)	−0.0062 (16)	0.0072 (14)	−0.0060 (15)
C19	0.0635 (18)	0.0525 (18)	0.0447 (16)	−0.0050 (14)	−0.0041 (14)	−0.0028 (14)
C4	0.0476 (17)	0.081 (2)	0.0580 (18)	−0.0044 (16)	0.0071 (15)	−0.0069 (17)
C15	0.0541 (18)	0.0596 (19)	0.0526 (17)	−0.0054 (15)	−0.0050 (14)	−0.0059 (15)
C11	0.0656 (19)	0.067 (2)	0.0497 (17)	0.0071 (16)	−0.0064 (15)	−0.0097 (16)
C5	0.0551 (19)	0.0623 (19)	0.0549 (18)	−0.0030 (15)	−0.0094 (15)	−0.0046 (15)
C13	0.060 (2)	0.064 (2)	0.068 (2)	0.0044 (16)	−0.0051 (17)	0.0044 (18)
C12	0.077 (2)	0.077 (2)	0.0534 (18)	0.0050 (18)	−0.0186 (17)	−0.0039 (17)
C8	0.056 (2)	0.102 (3)	0.092 (3)	−0.0092 (19)	−0.0091 (18)	−0.018 (2)
C17	0.066 (2)	0.109 (3)	0.076 (2)	0.021 (2)	0.0092 (18)	0.022 (2)
C16	0.105 (3)	0.093 (3)	0.121 (3)	0.047 (2)	−0.004 (3)	0.013 (3)

O1—C1	1.266 (3)	O6—C16	1.420 (4)
O4—C9	1.269 (3)	C6—C5	1.383 (4)
O5—C9	1.250 (3)	C6—H6A	0.9300
N1—C18	1.492 (3)	C14—C15	1.377 (4)
N1—H1A	0.9004	C14—C13	1.384 (4)
N1—H1B	0.9002	C14—H14A	0.9300
N1—H1C	0.9004	C3—C4	1.381 (4)
C10—C15	1.377 (4)	C3—H3A	0.9300
C10—C11	1.396 (4)	C19—H19A	0.9700
C10—C9	1.505 (4)	C19—H19B	0.9700
O2—C1	1.253 (3)	C4—C5	1.393 (4)
N2—C19	1.481 (3)	C4—H4A	0.9300
N2—H2A	0.9003	C15—H15A	0.9300
N2—H2B	0.9006	C11—C12	1.375 (4)
N2—H2C	0.9005	C11—H11A	0.9300
C2—C7	1.387 (4)	C13—C12	1.385 (4)
C2—C3	1.390 (4)	C12—H12A	0.9300
C2—C1	1.495 (4)	C8—H8A	0.9600
O3—C5	1.362 (3)	C8—H8B	0.9600
O3—C8	1.434 (3)	C8—H8C	0.9600
C7—C6	1.372 (4)	C17—H17A	0.9600
C7—H7A	0.9300	C17—H17B	0.9600
C18—C17	1.500 (4)	C17—H17C	0.9600
C18—C19	1.511 (4)	C16—H16A	0.9600
C18—H18A	0.9800	C16—H16B	0.9600
O6—C13	1.372 (4)	C16—H16C	0.9600
C18—N1—H1A	109.7	C2—C3—H3A	119.2
C18—N1—H1B	110.5	N2—C19—C18	114.4 (2)
H1A—N1—H1B	105.2	N2—C19—H19A	108.6
C18—N1—H1C	114.2	C18—C19—H19A	108.6
H1A—N1—H1C	106.1	N2—C19—H19B	108.6
H1B—N1—H1C	110.6	C18—C19—H19B	108.6
C15—C10—C11	118.1 (3)	H19A—C19—H19B	107.6
C15—C10—C9	122.4 (3)	C3—C4—C5	119.6 (3)
C11—C10—C9	119.5 (3)	C3—C4—H4A	120.2
C19—N2—H2A	104.5	C5—C4—H4A	120.2
C19—N2—H2B	110.8	C10—C15—C14	121.9 (3)
H2A—N2—H2B	113.0	C10—C15—H15A	119.0
C19—N2—H2C	113.8	C14—C15—H15A	119.0
H2A—N2—H2C	105.3	C12—C11—C10	120.8 (3)
H2B—N2—H2C	109.3	C12—C11—H11A	119.6
C7—C2—C3	117.4 (3)	C10—C11—H11A	119.6
C7—C2—C1	122.1 (2)	O3—C5—C6	116.0 (3)
C3—C2—C1	120.5 (3)	O3—C5—C4	124.7 (3)
O2—C1—O1	122.8 (3)	C6—C5—C4	119.3 (3)
O2—C1—C2	118.7 (2)	O6—C13—C14	125.1 (3)
O1—C1—C2	118.5 (2)	O6—C13—C12	115.0 (3)
O5—C9—O4	123.1 (3)	C14—C13—C12	119.9 (3)
O5—C9—C10	118.9 (3)	C11—C12—C13	120.0 (3)
O4—C9—C10	118.1 (3)	C11—C12—H12A	120.0
C5—O3—C8	117.9 (2)	C13—C12—H12A	120.0
C6—C7—C2	122.0 (3)	O3—C8—H8A	109.5
C6—C7—H7A	119.0	O3—C8—H8B	109.5
C2—C7—H7A	119.0	H8A—C8—H8B	109.5
N1—C18—C17	110.7 (2)	O3—C8—H8C	109.5
N1—C18—C19	110.9 (2)	H8A—C8—H8C	109.5
C17—C18—C19	114.9 (2)	H8B—C8—H8C	109.5
N1—C18—H18A	106.7	C18—C17—H17A	109.5
C17—C18—H18A	106.7	C18—C17—H17B	109.5
C19—C18—H18A	106.7	H17A—C17—H17B	109.5
C13—O6—C16	119.1 (3)	C18—C17—H17C	109.5
C7—C6—C5	120.0 (3)	H17A—C17—H17C	109.5
C7—C6—H6A	120.0	H17B—C17—H17C	109.5
C5—C6—H6A	120.0	O6—C16—H16A	109.5
C15—C14—C13	119.3 (3)	O6—C16—H16B	109.5
C15—C14—H14A	120.4	H16A—C16—H16B	109.5
C13—C14—H14A	120.4	O6—C16—H16C	109.5
C4—C3—C2	121.6 (3)	H16A—C16—H16C	109.5
C4—C3—H3A	119.2	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.90	1.82	2.696 (3)	162
N1—H1B···O1	0.90	1.92	2.791 (3)	162
N1—H1C···O1ii	0.90	1.89	2.777 (3)	167
N2—H2A···O5iii	0.90	1.82	2.718 (3)	173
N2—H2B···O4iv	0.90	2.03	2.917 (3)	170
N2—H2C···O2ii	0.90	1.81	2.703 (3)	1670

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.90	1.82	2.696 (3)	162
N1—H1B⋯O1	0.90	1.92	2.791 (3)	162
N1—H1C⋯O1ii	0.90	1.89	2.777 (3)	167
N2—H2A⋯O5iii	0.90	1.82	2.718 (3)	173
N2—H2B⋯O4iv	0.90	2.03	2.917 (3)	170
N2—H2C⋯O2ii	0.90	1.81	2.703 (3)	1670

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .