Tris(ethyl-enediamine-κN,N')cobalt(III) aqua-tris-(oxalato-κO,O)indate(III).

In the cation of the title compound, [Co(C(2)H(8)N(2))(3)][In(C(2)O(4))(3)(H(2)O)], the Co(III) atom is coordinated by six N atoms from three ethyl-enediamine mol-ecules. The Co(III)-N bond lengths lie in the range 1.956 (4)-1.986 (4) Å. In the anion, the In(III) atom is seven-coordinated by six O atoms from three oxalate ligands and by a water mol-ecule. The cations and anions are linked by extensive O-H⋯O and N-H⋯O hydrogen bonds, forming a supermolecular network.

Related literature

For metal phosphates and germanates templated by metal complexes, see: Du et al. (2004 ▶); Pan et al. (2005 ▶, 2008 ▶); Wang et al. (2003a ▶,b ▶,c ▶). For coordination polymers templated by metal complexes, see: Pan et al. (2010a ▶,b ▶, 2011 ▶), Tong & Pan (2011 ▶).

Experimental

Crystal data

[Co(C2H8N2)3][In(C2O4)3(H2O)]

M = 636.14

Triclinic,

a = 7.5161 (15) Å

b = 10.921 (2) Å

c = 14.450 (3) Å

α = 79.43 (3)°

β = 80.13 (3)°

γ = 71.25 (3)°

V = 1096.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.89 mm−1

T = 293 K

0.3 × 0.2 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.6, T max = 0.8

11056 measured reflections

4988 independent reflections

4360 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.10

4988 reflections

300 parameters

Only H-atom displacement parameters refined

Δρmax = 1.32 e Å−3

Δρmin = −0.91 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811053736/fj2490sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053736/fj2490Isup2.hkl

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

[Co(C2H8N2)3][In(C2O4)3(H2O)]	Z = 2
Mr = 636.14	F(000) = 640
Triclinic, P1	Dx = 1.927 Mg m−3
a = 7.5161 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.921 (2) Å	Cell parameters from 10592 reflections
c = 14.450 (3) Å	θ = 3.0–27.5°
α = 79.43 (3)°	µ = 1.89 mm−1
β = 80.13 (3)°	T = 293 K
γ = 71.25 (3)°	Block, yellow
V = 1096.1 (4) Å3	0.3 × 0.2 × 0.18 mm

Rigaku R-AXIS RAPID-S diffractometer	4988 independent reflections
Radiation source: fine-focus sealed tube	4360 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	h = −9→9
Tmin = 0.6, Tmax = 0.8	k = −14→14
11056 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	Only H-atom displacement parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.7829P] where P = (Fo2 + 2Fc2)/3
4988 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 1.32 e Å−3
0 restraints	Δρmin = −0.91 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
In1	0.41280 (4)	0.27178 (3)	0.70832 (2)	0.02767 (11)
Co1	0.13688 (7)	0.26192 (5)	1.23880 (4)	0.02715 (15)
O1	0.2854 (5)	0.4022 (3)	0.8190 (2)	0.0379 (7)
O2	0.2698 (5)	0.4142 (3)	0.9718 (2)	0.0490 (9)
O3	0.5453 (5)	0.1704 (3)	0.8361 (2)	0.0402 (8)
O4	0.5603 (6)	0.1847 (4)	0.9864 (3)	0.0681 (12)
O5	0.1303 (4)	0.2508 (3)	0.7207 (3)	0.0400 (8)
O6	−0.0236 (4)	0.1146 (3)	0.7043 (3)	0.0480 (9)
O7	0.4574 (4)	0.0573 (3)	0.7116 (2)	0.0386 (7)
O8	0.2982 (5)	−0.0880 (3)	0.7345 (3)	0.0517 (9)
O9	0.4602 (5)	0.2478 (3)	0.5559 (2)	0.0449 (8)
O10	0.4079 (6)	0.3539 (4)	0.4111 (2)	0.0564 (10)
O11	0.2819 (4)	0.4654 (3)	0.6321 (2)	0.0349 (7)
O12	0.2215 (6)	0.5763 (4)	0.4920 (3)	0.0660 (12)
O13	0.6771 (4)	0.3184 (3)	0.6787 (2)	0.0382 (7)
H13A	0.690 (3)	0.380 (4)	0.628 (3)	0.080*
H13B	0.792 (5)	0.272 (2)	0.686 (3)	0.080*
N1	−0.1017 (6)	0.2554 (4)	1.3206 (3)	0.0410 (9)
H1A	−0.1676	0.3355	1.3353	0.080*
H1B	−0.1734	0.2288	1.2894	0.080*
N2	0.2587 (5)	0.1761 (4)	1.3530 (3)	0.0353 (8)
H2A	0.3232	0.0924	1.3464	0.080*
H2B	0.3414	0.2163	1.3607	0.080*
N3	0.1680 (5)	0.0943 (3)	1.1973 (3)	0.0362 (8)
H3A	0.2883	0.0433	1.2001	0.080*
H3B	0.0917	0.0534	1.2364	0.080*
N4	0.0045 (6)	0.3375 (4)	1.1268 (3)	0.0394 (9)
H4A	−0.1014	0.4015	1.1420	0.080*
H4B	0.0790	0.3727	1.0815	0.080*
N5	0.3809 (5)	0.2696 (3)	1.1686 (3)	0.0334 (8)
H5A	0.4736	0.2015	1.1922	0.080*
H5B	0.3818	0.2628	1.1074	0.080*
N6	0.1154 (5)	0.4369 (4)	1.2661 (3)	0.0376 (9)
H6A	−0.0062	0.4868	1.2690	0.080*
H6B	0.1564	0.4305	1.3223	0.080*
C1	−0.0561 (8)	0.1636 (5)	1.4084 (4)	0.0488 (12)
H1C	−0.0303	0.0745	1.3967	0.080*
H1D	−0.1620	0.1822	1.4579	0.080*
C2	0.1141 (8)	0.1807 (5)	1.4380 (4)	0.0489 (12)
H2C	0.0817	0.2637	1.4616	0.080*
H2D	0.1630	0.1115	1.4881	0.080*
C3	0.1212 (8)	0.1146 (5)	1.0987 (4)	0.0470 (12)
H3C	0.0886	0.0404	1.0866	0.080*
H3D	0.2283	0.1253	1.0534	0.080*
C4	−0.0453 (8)	0.2366 (5)	1.0901 (4)	0.0490 (13)
H4C	−0.0684	0.2643	1.0244	0.080*
H4D	−0.1584	0.2208	1.1269	0.080*
C5	0.4190 (7)	0.3938 (4)	1.1746 (3)	0.0388 (10)
H5C	0.4919	0.4199	1.1165	0.080*
H5D	0.4909	0.3819	1.2270	0.080*
C6	0.2320 (7)	0.4966 (4)	1.1895 (3)	0.0384 (10)
H6C	0.2491	0.5728	1.2078	0.080*
H6D	0.1718	0.5228	1.1318	0.080*
C7	0.3368 (6)	0.3589 (4)	0.9016 (3)	0.0349 (10)
C8	0.4958 (7)	0.2256 (4)	0.9099 (3)	0.0396 (10)
C9	0.1204 (6)	0.1394 (4)	0.7148 (3)	0.0345 (10)
C10	0.3067 (6)	0.0259 (4)	0.7209 (3)	0.0347 (10)
C11	0.3953 (7)	0.3486 (5)	0.4982 (3)	0.0392 (11)
C12	0.2895 (6)	0.4741 (4)	0.5431 (3)	0.0380 (10)

	U11	U22	U33	U12	U13	U23
In1	0.02796 (18)	0.02283 (16)	0.03195 (19)	−0.00503 (12)	−0.00555 (12)	−0.00598 (11)
Co1	0.0254 (3)	0.0220 (3)	0.0337 (3)	−0.0050 (2)	−0.0045 (2)	−0.0058 (2)
O1	0.0447 (19)	0.0308 (15)	0.0320 (17)	0.0010 (13)	−0.0064 (14)	−0.0096 (13)
O2	0.063 (2)	0.0385 (18)	0.0382 (19)	−0.0011 (16)	−0.0030 (16)	−0.0148 (15)
O3	0.049 (2)	0.0324 (16)	0.0285 (17)	0.0043 (14)	−0.0057 (14)	−0.0049 (13)
O4	0.084 (3)	0.064 (2)	0.035 (2)	0.017 (2)	−0.021 (2)	−0.0108 (17)
O5	0.0311 (16)	0.0246 (15)	0.064 (2)	−0.0069 (13)	−0.0073 (15)	−0.0074 (14)
O6	0.0311 (17)	0.0337 (17)	0.081 (3)	−0.0111 (14)	−0.0150 (17)	−0.0010 (16)
O7	0.0299 (16)	0.0235 (14)	0.064 (2)	−0.0061 (12)	−0.0103 (15)	−0.0092 (14)
O8	0.045 (2)	0.0237 (15)	0.090 (3)	−0.0096 (14)	−0.0235 (19)	−0.0037 (16)
O9	0.062 (2)	0.0368 (17)	0.0375 (19)	−0.0119 (16)	−0.0079 (16)	−0.0119 (14)
O10	0.088 (3)	0.064 (2)	0.0312 (19)	−0.037 (2)	−0.0131 (18)	−0.0094 (16)
O11	0.0371 (17)	0.0289 (15)	0.0360 (18)	−0.0072 (13)	−0.0048 (13)	−0.0018 (12)
O12	0.074 (3)	0.054 (2)	0.045 (2)	0.003 (2)	−0.001 (2)	0.0100 (18)
O13	0.0284 (16)	0.0433 (18)	0.0405 (19)	−0.0103 (14)	−0.0089 (14)	0.0036 (14)
N1	0.037 (2)	0.036 (2)	0.051 (3)	−0.0107 (17)	−0.0003 (18)	−0.0150 (18)
N2	0.034 (2)	0.038 (2)	0.032 (2)	−0.0093 (16)	−0.0043 (16)	−0.0031 (15)
N3	0.035 (2)	0.0281 (18)	0.045 (2)	−0.0071 (16)	−0.0074 (17)	−0.0065 (16)
N4	0.037 (2)	0.0297 (19)	0.051 (2)	−0.0055 (16)	−0.0143 (18)	−0.0031 (17)
N5	0.034 (2)	0.0295 (18)	0.034 (2)	−0.0058 (15)	−0.0048 (16)	−0.0040 (15)
N6	0.035 (2)	0.0336 (19)	0.045 (2)	−0.0090 (16)	−0.0006 (17)	−0.0140 (16)
C1	0.053 (3)	0.050 (3)	0.046 (3)	−0.025 (3)	0.013 (2)	−0.014 (2)
C2	0.053 (3)	0.058 (3)	0.037 (3)	−0.021 (3)	0.001 (2)	−0.009 (2)
C3	0.065 (3)	0.041 (3)	0.042 (3)	−0.020 (2)	−0.013 (2)	−0.011 (2)
C4	0.054 (3)	0.046 (3)	0.055 (3)	−0.016 (2)	−0.026 (3)	−0.006 (2)
C5	0.040 (3)	0.039 (2)	0.043 (3)	−0.018 (2)	−0.002 (2)	−0.010 (2)
C6	0.047 (3)	0.027 (2)	0.045 (3)	−0.016 (2)	−0.008 (2)	−0.0044 (19)
C7	0.035 (2)	0.028 (2)	0.040 (3)	−0.0077 (18)	−0.0037 (19)	−0.0062 (18)
C8	0.042 (3)	0.038 (2)	0.034 (3)	−0.006 (2)	−0.006 (2)	−0.0024 (19)
C9	0.029 (2)	0.029 (2)	0.045 (3)	−0.0074 (18)	−0.0074 (19)	−0.0020 (18)
C10	0.037 (2)	0.025 (2)	0.044 (3)	−0.0088 (18)	−0.014 (2)	−0.0025 (18)
C11	0.048 (3)	0.045 (3)	0.033 (3)	−0.024 (2)	−0.009 (2)	−0.005 (2)
C12	0.034 (2)	0.037 (2)	0.040 (3)	−0.0125 (19)	−0.002 (2)	0.0031 (19)

In1—O13	2.160 (3)	N2—H2B	0.9000
In1—O5	2.182 (3)	N3—C3	1.487 (6)
In1—O3	2.191 (3)	N3—H3A	0.9000
In1—O11	2.199 (3)	N3—H3B	0.9000
In1—O9	2.221 (3)	N4—C4	1.477 (6)
In1—O1	2.222 (3)	N4—H4A	0.9000
In1—O7	2.250 (3)	N4—H4B	0.9000
Co1—N4	1.956 (4)	N5—C5	1.494 (5)
Co1—N5	1.957 (4)	N5—H5A	0.9000
Co1—N2	1.959 (4)	N5—H5B	0.9000
Co1—N3	1.960 (4)	N6—C6	1.479 (6)
Co1—N6	1.972 (4)	N6—H6A	0.9000
Co1—N1	1.986 (4)	N6—H6B	0.9000
O1—C7	1.277 (5)	C1—C2	1.492 (7)
O2—C7	1.225 (5)	C1—H1C	0.9700
O3—C8	1.263 (5)	C1—H1D	0.9700
O4—C8	1.234 (6)	C2—H2C	0.9700
O5—C9	1.262 (5)	C2—H2D	0.9700
O6—C9	1.236 (5)	C3—C4	1.509 (7)
O7—C10	1.265 (5)	C3—H3C	0.9700
O8—C10	1.244 (5)	C3—H3D	0.9700
O9—C11	1.266 (6)	C4—H4C	0.9700
O10—C11	1.238 (6)	C4—H4D	0.9700
O11—C12	1.265 (5)	C5—C6	1.501 (6)
O12—C12	1.230 (6)	C5—H5C	0.9700
O13—H13A	0.9135	C5—H5D	0.9700
O13—H13B	0.8610	C6—H6C	0.9700
N1—C1	1.481 (7)	C6—H6D	0.9700
N1—H1A	0.9000	C7—C8	1.559 (6)
N1—H1B	0.9000	C9—C10	1.546 (6)
N2—C2	1.491 (6)	C11—C12	1.543 (7)
N2—H2A	0.9000
O13—In1—O5	170.86 (11)	H4A—N4—H4B	108.1
O13—In1—O3	79.09 (12)	C5—N5—Co1	111.8 (3)
O5—In1—O3	109.59 (13)	C5—N5—H5A	109.3
O13—In1—O11	87.46 (12)	Co1—N5—H5A	109.3
O5—In1—O11	83.75 (12)	C5—N5—H5B	109.3
O3—In1—O11	143.84 (12)	Co1—N5—H5B	109.3
O13—In1—O9	84.67 (13)	H5A—N5—H5B	107.9
O5—In1—O9	90.49 (13)	C6—N6—Co1	108.4 (3)
O3—In1—O9	136.66 (12)	C6—N6—H6A	110.0
O11—In1—O9	73.94 (12)	Co1—N6—H6A	110.0
O13—In1—O1	95.45 (12)	C6—N6—H6B	110.0
O5—In1—O1	84.56 (12)	Co1—N6—H6B	110.0
O3—In1—O1	73.95 (11)	H6A—N6—H6B	108.4
O11—In1—O1	74.14 (11)	N1—C1—C2	107.7 (4)
O9—In1—O1	148.04 (12)	N1—C1—H1C	110.2
O13—In1—O7	111.82 (12)	C2—C1—H1C	110.2
O5—In1—O7	74.38 (11)	N1—C1—H1D	110.2
O3—In1—O7	72.79 (12)	C2—C1—H1D	110.2
O11—In1—O7	142.94 (12)	H1C—C1—H1D	108.5
O9—In1—O7	76.66 (12)	N2—C2—C1	107.3 (4)
O1—In1—O7	131.28 (12)	N2—C2—H2C	110.2
N4—Co1—N5	92.52 (17)	C1—C2—H2C	110.2
N4—Co1—N2	175.52 (16)	N2—C2—H2D	110.2
N5—Co1—N2	90.62 (16)	C1—C2—H2D	110.2
N4—Co1—N3	84.54 (16)	H2C—C2—H2D	108.5
N5—Co1—N3	91.28 (16)	N3—C3—C4	106.4 (4)
N2—Co1—N3	92.20 (16)	N3—C3—H3C	110.5
N4—Co1—N6	91.28 (16)	C4—C3—H3C	110.5
N5—Co1—N6	84.23 (15)	N3—C3—H3D	110.5
N2—Co1—N6	92.22 (16)	C4—C3—H3D	110.5
N3—Co1—N6	173.73 (16)	H3C—C3—H3D	108.6
N4—Co1—N1	92.14 (18)	N4—C4—C3	106.5 (4)
N5—Co1—N1	174.76 (16)	N4—C4—H4C	110.4
N2—Co1—N1	84.87 (17)	C3—C4—H4C	110.4
N3—Co1—N1	91.56 (16)	N4—C4—H4D	110.4
N6—Co1—N1	93.26 (16)	C3—C4—H4D	110.4
C7—O1—In1	116.6 (3)	H4C—C4—H4D	108.6
C8—O3—In1	118.2 (3)	N5—C5—C6	107.9 (4)
C9—O5—In1	117.0 (3)	N5—C5—H5C	110.1
C10—O7—In1	114.6 (3)	C6—C5—H5C	110.1
C11—O9—In1	116.8 (3)	N5—C5—H5D	110.1
C12—O11—In1	116.9 (3)	C6—C5—H5D	110.1
In1—O13—H13A	118.1	H5C—C5—H5D	108.4
In1—O13—H13B	132.1	N6—C6—C5	106.2 (4)
H13A—O13—H13B	104.0	N6—C6—H6C	110.5
C1—N1—Co1	109.3 (3)	C5—C6—H6C	110.5
C1—N1—H1A	109.8	N6—C6—H6D	110.5
Co1—N1—H1A	109.8	C5—C6—H6D	110.5
C1—N1—H1B	109.8	H6C—C6—H6D	108.7
Co1—N1—H1B	109.8	O2—C7—O1	124.7 (4)
H1A—N1—H1B	108.3	O2—C7—C8	119.9 (4)
C2—N2—Co1	110.4 (3)	O1—C7—C8	115.4 (4)
C2—N2—H2A	109.6	O4—C8—O3	126.7 (4)
Co1—N2—H2A	109.6	O4—C8—C7	117.8 (4)
C2—N2—H2B	109.6	O3—C8—C7	115.6 (4)
Co1—N2—H2B	109.6	O6—C9—O5	125.6 (4)
H2A—N2—H2B	108.1	O6—C9—C10	118.4 (4)
C3—N3—Co1	110.6 (3)	O5—C9—C10	116.0 (4)
C3—N3—H3A	109.5	O8—C10—O7	125.0 (4)
Co1—N3—H3A	109.5	O8—C10—C9	118.4 (4)
C3—N3—H3B	109.5	O7—C10—C9	116.5 (4)
Co1—N3—H3B	109.5	O10—C11—O9	125.9 (5)
H3A—N3—H3B	108.1	O10—C11—C12	118.6 (4)
C4—N4—Co1	110.6 (3)	O9—C11—C12	115.5 (4)
C4—N4—H4A	109.5	O12—C12—O11	123.6 (5)
Co1—N4—H4A	109.5	O12—C12—C11	119.6 (4)
C4—N4—H4B	109.5	O11—C12—C11	116.8 (4)
Co1—N4—H4B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···O12i	0.91	1.79	2.620 (5)	150
O13—H13B···O6ii	0.86	1.84	2.629 (4)	152
N1—H1A···O11iii	0.90	2.17	3.064 (5)	171
N1—H1B···O8iv	0.90	2.14	2.972 (5)	153
N2—H2A···O7v	0.90	2.10	2.935 (5)	155
N2—H2B···O10vi	0.90	2.01	2.838 (5)	152
N3—H3A···O7v	0.90	2.34	3.142 (5)	149
N3—H3A···O3v	0.90	2.37	3.063 (5)	134
N3—H3B···O6iv	0.90	2.06	2.878 (5)	151
N4—H4A···O1iii	0.90	2.26	3.114 (5)	159
N4—H4A···O2iii	0.90	2.49	3.103 (5)	126
N4—H4B···O2	0.90	2.04	2.924 (6)	168
N5—H5A···O8v	0.90	2.09	2.962 (5)	163
N5—H5B···O4	0.90	2.14	2.912 (5)	143
N5—H5B···O2	0.90	2.40	3.099 (5)	135
N6—H6A···O11iii	0.90	2.27	3.040 (5)	143
N6—H6A···O1iii	0.90	2.49	3.279 (5)	147
N6—H6B···O10vi	0.90	2.31	3.105 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13A⋯O12i	0.91	1.79	2.620 (5)	150
O13—H13B⋯O6ii	0.86	1.84	2.629 (4)	152
N1—H1A⋯O11iii	0.90	2.17	3.064 (5)	171
N1—H1B⋯O8iv	0.90	2.14	2.972 (5)	153
N2—H2A⋯O7v	0.90	2.10	2.935 (5)	155
N2—H2B⋯O10vi	0.90	2.01	2.838 (5)	152
N3—H3A⋯O7v	0.90	2.34	3.142 (5)	149
N3—H3A⋯O3v	0.90	2.37	3.063 (5)	134
N3—H3B⋯O6iv	0.90	2.06	2.878 (5)	151
N4—H4A⋯O1iii	0.90	2.26	3.114 (5)	159
N4—H4A⋯O2iii	0.90	2.49	3.103 (5)	126
N4—H4B⋯O2	0.90	2.04	2.924 (6)	168
N5—H5A⋯O8v	0.90	2.09	2.962 (5)	163
N5—H5B⋯O4	0.90	2.14	2.912 (5)	143
N5—H5B⋯O2	0.90	2.40	3.099 (5)	135
N6—H6A⋯O11iii	0.90	2.27	3.040 (5)	143
N6—H6A⋯O1iii	0.90	2.49	3.279 (5)	147
N6—H6B⋯O10vi	0.90	2.31	3.105 (5)	147

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