N,N-Dimethyl-propane-1,2-diaminium bis-(6-carb-oxy-pyridine-2-carboxyl-ate) monohydrate.

The asymmetric unit of the title proton-transfer compound, C(5)H(16)N(2) (2+)·2C(7)H(4)NO(4) (-)·H(2)O, consists of two mono-deproton-ated pyridine-2,6-dicarb-oxy-lic acid mol-ecules as anions, viz. (py-2,6-dcH)(-), one diprotonated N(1),N(1)-dimethyl-propane-1,2-diamine mol-ecule as a cation, viz. (dmpdaH(2))(2+), and one water mol-ecule. The crystal packing shows extensive O-H⋯O, N-H⋯O, N-H⋯N and O-H⋯N and weak inter-molecular C-H⋯O hydrogen bonds. These inter-actions link the (dmpdaH(2))(2+) cation, the (py-2,6-dcH)(-) anions and water mol-ecule and play an important role in the stabilization of crystal packing.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ▶). For related structures, see: Aghabozorg, Bayan et al. (2011 ▶); Aghabozorg, Mofidi Rouchi et al. (2011 ▶); Aghabozorg, Saemi et al. (2011 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C5H16N2 2+·2C7H4NO4 −·H2O

M = 454.44

Orthorhombic,

a = 11.826 (8) Å

b = 13.376 (8) Å

c = 13.479 (8) Å

V = 2132 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.42 × 0.38 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.708, T max = 0.746

70173 measured reflections

4650 independent reflections

4509 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.084

S = 1.07

4650 reflections

298 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009287/vm2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009287/vm2081Isup2.hkl

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

C5H16N22+·2C7H4NO4−·H2O	F(000) = 960
Mr = 454.44	Dx = 1.416 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 296(2) reflections
a = 11.826 (8) Å	θ = 2.2–27.0°
b = 13.376 (8) Å	µ = 0.11 mm−1
c = 13.479 (8) Å	T = 293 K
V = 2132 (2) Å3	Irregular, colorless
Z = 4	0.42 × 0.38 × 0.22 mm

Bruker APEXII CCD diffractometer	4650 independent reflections
Radiation source: fine-focus sealed tube	4509 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.708, Tmax = 0.746	k = −17→17
70173 measured reflections	l = −17→17

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.2616P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4650 reflections	Δρmax = 0.23 e Å−3
298 parameters	Δρmin = −0.18 e Å−3
3 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: 0.0064 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.82378 (16)	0.49387 (15)	0.59189 (15)	0.0608 (4)
H10A	0.7917	0.5578	0.6078	0.091*
H10B	0.8457	0.4929	0.5233	0.091*
H10C	0.8890	0.4823	0.6328	0.091*
C2	0.78465 (16)	0.31373 (12)	0.58604 (14)	0.0589 (4)
H20A	0.7278	0.2639	0.5979	0.088*
H20B	0.8493	0.3005	0.6271	0.088*
H20C	0.8067	0.3119	0.5175	0.088*
C3	0.63379 (12)	0.43601 (10)	0.55191 (10)	0.0410 (3)
H3B	0.6481	0.4194	0.4830	0.049*
H3C	0.6194	0.5073	0.5552	0.049*
C4	0.52821 (12)	0.38176 (9)	0.58465 (9)	0.0352 (3)
H4	0.5460	0.3112	0.5963	0.042*
C5	0.44060 (16)	0.38990 (14)	0.50382 (12)	0.0557 (4)
H5A	0.3731	0.3555	0.5239	0.084*
H5B	0.4694	0.3603	0.4440	0.084*
H5C	0.4235	0.4591	0.4921	0.084*
C6	0.51400 (11)	0.21400 (9)	0.86340 (10)	0.0361 (3)
C7	0.44510 (11)	0.29707 (9)	0.91060 (9)	0.0323 (2)
C8	0.34944 (14)	0.27536 (10)	0.96579 (11)	0.0469 (3)
H8	0.3263	0.2095	0.9746	0.056*
C9	0.28930 (15)	0.35256 (12)	1.00737 (13)	0.0547 (4)
H9	0.2244	0.3398	1.0442	0.066*
C10	0.32657 (12)	0.44927 (11)	0.99364 (11)	0.0433 (3)
H10	0.2881	0.5029	1.0218	0.052*
C11	0.42230 (10)	0.46459 (9)	0.93714 (9)	0.0309 (2)
C12	0.46436 (11)	0.56979 (9)	0.91995 (9)	0.0347 (3)
C13	0.74414 (11)	0.71223 (9)	0.80029 (10)	0.0360 (3)
C14	0.81762 (10)	0.79792 (9)	0.76580 (10)	0.0327 (2)
C15	0.92660 (12)	0.77789 (11)	0.73243 (12)	0.0446 (3)
H15	0.9531	0.7125	0.7291	0.054*
C16	0.99431 (12)	0.85656 (12)	0.70449 (13)	0.0490 (4)
H16	1.0672	0.8452	0.6812	0.059*
C17	0.95259 (11)	0.95225 (11)	0.71152 (10)	0.0402 (3)
H17	0.9975	1.0069	0.6951	0.048*
C18	0.84204 (10)	0.96563 (9)	0.74366 (9)	0.0315 (2)
C19	0.79612 (10)	1.07016 (9)	0.75010 (9)	0.0330 (2)
N1	0.73847 (10)	0.41412 (9)	0.61018 (8)	0.0399 (3)
H1	0.7203	0.4150	0.6758	0.048*
N2	0.47949 (9)	0.42609 (8)	0.67685 (8)	0.0340 (2)
H1A	0.5298	0.4217	0.7258	0.051*
H2A	0.4171	0.3930	0.6936	0.051*
H3A	0.4626	0.4900	0.6661	0.051*
N3	0.48126 (8)	0.39046 (7)	0.89568 (7)	0.0291 (2)
N4	0.77430 (8)	0.89011 (7)	0.76994 (7)	0.0295 (2)
O1	0.59431 (8)	0.23905 (6)	0.80781 (8)	0.0420 (2)
O2	0.48705 (13)	0.12753 (7)	0.88430 (10)	0.0636 (4)
O3	0.54684 (9)	0.57393 (7)	0.85809 (8)	0.0454 (2)
H3	0.5668	0.6322	0.8511	0.068*
O4	0.42263 (12)	0.63994 (8)	0.96310 (10)	0.0592 (3)
O5	0.64280 (8)	0.73404 (6)	0.82184 (8)	0.0417 (2)
O6	0.78683 (10)	0.62868 (7)	0.80691 (11)	0.0570 (3)
O7	0.68767 (8)	1.07388 (7)	0.76530 (8)	0.0428 (2)
H7	0.6673	1.1324	0.7681	0.064*
O8	0.85621 (10)	1.14190 (8)	0.74214 (11)	0.0578 (3)
O9	0.72243 (10)	0.42389 (9)	0.81056 (8)	0.0489 (3)
H9A	0.6703 (19)	0.3950 (18)	0.835 (2)	0.099 (9)*
H9B	0.711 (3)	0.4830 (14)	0.827 (2)	0.115 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0545 (9)	0.0633 (10)	0.0645 (10)	−0.0123 (8)	0.0124 (8)	−0.0003 (8)
C2	0.0586 (10)	0.0474 (9)	0.0706 (10)	0.0237 (8)	0.0006 (8)	−0.0045 (8)
C3	0.0424 (7)	0.0358 (6)	0.0446 (7)	0.0094 (6)	0.0129 (5)	0.0066 (6)
C4	0.0431 (7)	0.0256 (5)	0.0370 (6)	0.0036 (5)	0.0063 (5)	−0.0008 (5)
C5	0.0664 (10)	0.0583 (9)	0.0423 (7)	−0.0145 (8)	−0.0085 (7)	−0.0005 (7)
C6	0.0419 (6)	0.0232 (5)	0.0431 (6)	0.0004 (5)	0.0016 (5)	0.0027 (5)
C7	0.0382 (6)	0.0248 (5)	0.0340 (5)	−0.0014 (5)	0.0030 (5)	0.0020 (4)
C8	0.0547 (8)	0.0329 (7)	0.0529 (8)	−0.0130 (6)	0.0179 (7)	−0.0007 (6)
C9	0.0528 (9)	0.0525 (8)	0.0587 (9)	−0.0150 (7)	0.0298 (8)	−0.0087 (7)
C10	0.0406 (7)	0.0406 (7)	0.0489 (7)	0.0015 (5)	0.0156 (6)	−0.0094 (6)
C11	0.0322 (6)	0.0276 (5)	0.0327 (5)	0.0004 (5)	0.0011 (5)	−0.0007 (4)
C12	0.0375 (6)	0.0256 (5)	0.0411 (6)	0.0034 (5)	−0.0008 (5)	−0.0004 (5)
C13	0.0369 (6)	0.0256 (5)	0.0455 (7)	0.0014 (5)	−0.0014 (5)	−0.0007 (5)
C14	0.0296 (6)	0.0273 (5)	0.0412 (6)	0.0026 (4)	0.0001 (5)	0.0010 (5)
C15	0.0341 (6)	0.0351 (6)	0.0647 (9)	0.0091 (5)	0.0054 (6)	0.0012 (6)
C16	0.0283 (6)	0.0533 (8)	0.0654 (9)	0.0069 (6)	0.0112 (6)	0.0066 (7)
C17	0.0292 (6)	0.0420 (7)	0.0495 (7)	−0.0043 (5)	0.0044 (5)	0.0083 (6)
C18	0.0294 (5)	0.0295 (6)	0.0357 (6)	−0.0009 (4)	−0.0008 (5)	0.0046 (4)
C19	0.0317 (5)	0.0283 (5)	0.0391 (6)	−0.0024 (5)	0.0002 (5)	0.0053 (5)
N1	0.0420 (6)	0.0376 (6)	0.0400 (5)	0.0045 (5)	0.0107 (5)	−0.0022 (4)
N2	0.0305 (5)	0.0362 (5)	0.0353 (5)	−0.0017 (4)	0.0039 (4)	−0.0012 (4)
N3	0.0299 (5)	0.0238 (4)	0.0335 (5)	0.0005 (4)	0.0034 (4)	0.0018 (4)
N4	0.0267 (4)	0.0255 (4)	0.0363 (5)	0.0006 (4)	0.0008 (4)	0.0017 (4)
O1	0.0368 (4)	0.0260 (4)	0.0632 (6)	0.0017 (4)	0.0110 (4)	−0.0009 (4)
O2	0.0880 (9)	0.0216 (4)	0.0814 (8)	0.0001 (5)	0.0362 (7)	0.0061 (5)
O3	0.0495 (5)	0.0229 (4)	0.0637 (6)	−0.0027 (4)	0.0157 (5)	0.0024 (4)
O4	0.0746 (8)	0.0288 (5)	0.0742 (8)	0.0032 (5)	0.0236 (7)	−0.0083 (5)
O5	0.0334 (4)	0.0256 (4)	0.0660 (6)	−0.0011 (4)	0.0090 (4)	0.0041 (4)
O6	0.0486 (6)	0.0267 (5)	0.0956 (9)	0.0067 (4)	0.0086 (6)	0.0069 (5)
O7	0.0325 (4)	0.0244 (4)	0.0714 (6)	0.0015 (3)	0.0023 (4)	−0.0022 (4)
O8	0.0448 (6)	0.0313 (5)	0.0973 (9)	−0.0083 (4)	0.0141 (6)	0.0070 (5)
O9	0.0454 (6)	0.0497 (6)	0.0516 (6)	0.0039 (5)	0.0127 (5)	−0.0008 (5)

C1—N1	1.489 (2)	C10—H10	0.9300
C1—H10A	0.9600	C11—N3	1.3347 (15)
C1—H10B	0.9600	C11—C12	1.5104 (16)
C1—H10C	0.9600	C12—O4	1.2094 (16)
C2—N1	1.4857 (18)	C12—O3	1.2843 (16)
C2—H20A	0.9600	C13—O6	1.2296 (16)
C2—H20B	0.9600	C13—O5	1.2672 (16)
C2—H20C	0.9600	C13—C14	1.5117 (17)
C3—N1	1.4950 (19)	C14—N4	1.3364 (15)
C3—C4	1.5101 (18)	C14—C15	1.3910 (18)
C3—H3B	0.9700	C15—C16	1.375 (2)
C3—H3C	0.9700	C15—H15	0.9300
C4—N2	1.4926 (15)	C16—C17	1.375 (2)
C4—C5	1.507 (2)	C16—H16	0.9300
C4—H4	0.9800	C17—C18	1.3889 (17)
C5—H5A	0.9600	C17—H17	0.9300
C5—H5B	0.9600	C18—N4	1.3371 (15)
C5—H5C	0.9600	C18—C19	1.5025 (16)
C6—O2	1.2323 (16)	C19—O8	1.1988 (16)
C6—O1	1.2553 (16)	C19—O7	1.2996 (15)
C6—C7	1.5177 (17)	N1—H1	0.9100
C7—N3	1.3356 (15)	N2—H1A	0.8900
C7—C8	1.3848 (18)	N2—H2A	0.8900
C8—C9	1.373 (2)	N2—H3A	0.8900
C8—H8	0.9300	O3—H3	0.8200
C9—C10	1.379 (2)	O7—H7	0.8200
C9—H9	0.9300	O9—H9A	0.799 (17)
C10—C11	1.3798 (18)	O9—H9B	0.830 (17)
N1—C1—H10A	109.5	N3—C11—C10	123.33 (11)
N1—C1—H10B	109.5	N3—C11—C12	117.12 (10)
H10A—C1—H10B	109.5	C10—C11—C12	119.55 (11)
N1—C1—H10C	109.5	O4—C12—O3	126.07 (13)
H10A—C1—H10C	109.5	O4—C12—C11	120.98 (12)
H10B—C1—H10C	109.5	O3—C12—C11	112.94 (10)
N1—C2—H20A	109.5	O6—C13—O5	125.52 (13)
N1—C2—H20B	109.5	O6—C13—C14	118.39 (12)
H20A—C2—H20B	109.5	O5—C13—C14	116.08 (11)
N1—C2—H20C	109.5	N4—C14—C15	123.12 (12)
H20A—C2—H20C	109.5	N4—C14—C13	117.80 (11)
H20B—C2—H20C	109.5	C15—C14—C13	119.08 (11)
N1—C3—C4	115.91 (11)	C16—C15—C14	118.73 (13)
N1—C3—H3B	108.3	C16—C15—H15	120.6
C4—C3—H3B	108.3	C14—C15—H15	120.6
N1—C3—H3C	108.3	C15—C16—C17	118.99 (13)
C4—C3—H3C	108.3	C15—C16—H16	120.5
H3B—C3—H3C	107.4	C17—C16—H16	120.5
N2—C4—C5	107.93 (12)	C16—C17—C18	118.63 (12)
N2—C4—C3	111.82 (11)	C16—C17—H17	120.7
C5—C4—C3	108.80 (11)	C18—C17—H17	120.7
N2—C4—H4	109.4	N4—C18—C17	123.32 (12)
C5—C4—H4	109.4	N4—C18—C19	118.11 (10)
C3—C4—H4	109.4	C17—C18—C19	118.57 (11)
C4—C5—H5A	109.5	O8—C19—O7	124.64 (12)
C4—C5—H5B	109.5	O8—C19—C18	121.69 (11)
H5A—C5—H5B	109.5	O7—C19—C18	113.67 (10)
C4—C5—H5C	109.5	C2—N1—C1	111.23 (13)
H5A—C5—H5C	109.5	C2—N1—C3	111.49 (12)
H5B—C5—H5C	109.5	C1—N1—C3	109.50 (12)
O2—C6—O1	125.64 (13)	C2—N1—H1	108.2
O2—C6—C7	116.91 (12)	C1—N1—H1	108.2
O1—C6—C7	117.45 (10)	C3—N1—H1	108.2
N3—C7—C8	122.59 (12)	C4—N2—H1A	109.5
N3—C7—C6	116.73 (11)	C4—N2—H2A	109.5
C8—C7—C6	120.68 (11)	H1A—N2—H2A	109.5
C9—C8—C7	118.99 (12)	C4—N2—H3A	109.5
C9—C8—H8	120.5	H1A—N2—H3A	109.5
C7—C8—H8	120.5	H2A—N2—H3A	109.5
C8—C9—C10	119.01 (13)	C11—N3—C7	117.68 (10)
C8—C9—H9	120.5	C14—N4—C18	117.15 (10)
C10—C9—H9	120.5	C12—O3—H3	109.5
C9—C10—C11	118.40 (12)	C19—O7—H7	109.5
C9—C10—H10	120.8	H9A—O9—H9B	103 (3)
C11—C10—H10	120.8
N1—C3—C4—N2	75.97 (14)	N4—C14—C15—C16	1.6 (2)
N1—C3—C4—C5	−164.91 (12)	C13—C14—C15—C16	−177.73 (14)
O2—C6—C7—N3	173.61 (14)	C14—C15—C16—C17	0.7 (2)
O1—C6—C7—N3	−5.34 (18)	C15—C16—C17—C18	−2.0 (2)
O2—C6—C7—C8	−6.7 (2)	C16—C17—C18—N4	1.2 (2)
O1—C6—C7—C8	174.39 (14)	C16—C17—C18—C19	−179.26 (13)
N3—C7—C8—C9	−0.3 (2)	N4—C18—C19—O8	168.74 (14)
C6—C7—C8—C9	179.99 (14)	C17—C18—C19—O8	−10.81 (19)
C7—C8—C9—C10	−0.6 (3)	N4—C18—C19—O7	−10.92 (16)
C8—C9—C10—C11	1.0 (3)	C17—C18—C19—O7	169.53 (12)
C9—C10—C11—N3	−0.5 (2)	C4—C3—N1—C2	74.31 (15)
C9—C10—C11—C12	179.35 (14)	C4—C3—N1—C1	−162.17 (12)
N3—C11—C12—O4	−172.38 (13)	C10—C11—N3—C7	−0.30 (18)
C10—C11—C12—O4	7.7 (2)	C12—C11—N3—C7	179.80 (11)
N3—C11—C12—O3	6.62 (16)	C8—C7—N3—C11	0.73 (19)
C10—C11—C12—O3	−173.29 (12)	C6—C7—N3—C11	−179.55 (11)
O6—C13—C14—N4	−172.34 (13)	C15—C14—N4—C18	−2.43 (19)
O5—C13—C14—N4	6.38 (18)	C13—C14—N4—C18	176.91 (11)
O6—C13—C14—C15	7.0 (2)	C17—C18—N4—C14	1.00 (18)
O5—C13—C14—C15	−174.25 (13)	C19—C18—N4—C14	−178.52 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O9	0.91	1.82	2.711 (2)	165
N2—H1A···O9	0.89	2.55	3.392 (3)	158
N2—H1A···N3	0.89	2.40	2.988 (2)	124
N2—H2A···O5i	0.89	2.25	2.948 (2)	135
N2—H2A···N4i	0.89	2.32	3.123 (3)	151
O3—H3···O5	0.82	1.68	2.473 (2)	162
N2—H3A···O2ii	0.89	2.05	2.845 (2)	148
N2—H3A···O7i	0.89	2.30	2.902 (2)	125
O7—H7···O1iii	0.82	1.75	2.535 (2)	159
O9—H9A···O1	0.80 (2)	2.30 (2)	2.900 (2)	132 (2)
O9—H9A···N3	0.80 (2)	2.38 (2)	3.107 (3)	152 (2)
O9—H9B···O3	0.83 (2)	2.33 (3)	2.958 (3)	133 (3)
O9—H9B···O6	0.83 (2)	2.16 (2)	2.844 (2)	139 (3)
C3—H3B···O6iv	0.97	2.58	3.541 (3)	172
C3—H3C···O2ii	0.97	2.20	3.057 (3)	147
C4—H4···O4i	0.98	2.45	3.349 (3)	152
C15—H15···O8v	0.93	2.48	3.166 (3)	131
C2—H20A···O4i	0.96	2.57	3.443 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O9	0.91	1.82	2.711 (2)	165
N2—H1A⋯O9	0.89	2.55	3.392 (3)	158
N2—H1A⋯N3	0.89	2.40	2.988 (2)	124
N2—H2A⋯O5i	0.89	2.25	2.948 (2)	135
N2—H2A⋯N4i	0.89	2.32	3.123 (3)	151
O3—H3⋯O5	0.82	1.68	2.473 (2)	162
N2—H3A⋯O2ii	0.89	2.05	2.845 (2)	148
N2—H3A⋯O7i	0.89	2.30	2.902 (2)	125
O7—H7⋯O1iii	0.82	1.75	2.535 (2)	159
O9—H9A⋯O1	0.80 (2)	2.30 (2)	2.900 (2)	132 (2)
O9—H9A⋯N3	0.80 (2)	2.38 (2)	3.107 (3)	152 (2)
O9—H9B⋯O3	0.83 (2)	2.33 (3)	2.958 (3)	133 (3)
O9—H9B⋯O6	0.83 (2)	2.16 (2)	2.844 (2)	139 (3)
C3—H3B⋯O6iv	0.97	2.58	3.541 (3)	172
C3—H3C⋯O2ii	0.97	2.20	3.057 (3)	147
C4—H4⋯O4i	0.98	2.45	3.349 (3)	152
C15—H15⋯O8v	0.93	2.48	3.166 (3)	131
C2—H20A⋯O4i	0.96	2.57	3.443 (3)	152

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