catena-Poly[(μ(2)-3-carb-oxy-5-nitro-benzoato)(μ(3)-5-nitro-benzene-1,3-dicarboxyl-ato)(1,10-phenanthroline)gadolinium(III)].

The crystal structure of the title complex, [Gd(C(8)H(3)NO(6))(C(8)H(4)NO(6))(C(12)H(8)N(2))](n), contains polymeric chains made up of Gd(III) atoms, 1,10-phenanthroline and fully or half-deproton-ated 5-nitro-benzene-1,3-dicarb-oxy-lic acid (H(2)L) ligands. The Gd(III) atom is coordinated in a distorted bicapped trigonal-prismatic fashion by six O atoms from two HL(-) and three L(2-) ligands, and by two N atoms from the 1,10-phenanthroline ligand. The L(2-) ligands bridge the Gd-phenanthroline units, forming chains running parallel to [100]. O-H⋯O hydrogen bonding as well as π-π stacking inter-actions with an inter-planar distance of 3.599 (2) Å assemble neighboring polymeric chains.

Related literature

For background to π–π stacking in biological systems, see: Deisenhofer & Michel (1989 ▶). For some crystal structures of class="Chemical">metal complexes exhibiting π–π stacking, see: Li et al. (2005 ▶); Pan & Xu (2004 ▶); Wu et al. (2003 ▶); Qiu et al. (2009 ▶).

Experimental

Crystal data

[class="Chemical">Gd(C8H3NO6)(n class="Chemical">C8H4NO6)(C12H8N2)]

M = 756.69

Triclinic,

a = 10.300 (3) Å

b = 12.030 (3) Å

c = 12.150 (3) Å

α = 70.581 (4)°

β = 85.925 (4)°

γ = 76.512 (2)°

V = 1380.6 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.48 mm−1

T = 298 K

0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.544, T max = 0.612

6876 measured reflections

4837 independent reflections

4259 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.04

4837 reflections

407 parameters

H-atom parameters constrained

Δρmax = 2.51 e Å−3

Δρmin = −2.59 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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/S1600536810035452/wm2394sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035452/wm2394Isup2.hkl

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

[Gd(C8H3NO6)(C8H4NO6)(C12H8N2)]	Z = 2
Mr = 756.69	F(000) = 742
Triclinic, P1	Dx = 1.820 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.300 (3) Å	Cell parameters from 5111 reflections
b = 12.030 (3) Å	θ = 2.6–27.7°
c = 12.150 (3) Å	µ = 2.48 mm−1
α = 70.581 (4)°	T = 298 K
β = 85.925 (4)°	Prism, colorless
γ = 76.512 (2)°	0.28 × 0.26 × 0.22 mm
V = 1380.6 (7) Å3

Bruker SMART CCD area-detector diffractometer	4860 independent reflections
Radiation source: fine-focus sealed tube	4259 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scan	θmax = 25.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.544, Tmax = 0.612	k = −13→14
6896 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3
4837 reflections	(Δ/σ)max < 0.001
407 parameters	Δρmax = 2.51 e Å−3
0 restraints	Δρmin = −2.59 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
C1	1.0366 (7)	0.0929 (6)	0.6625 (5)	0.0330 (14)
C2	1.0511 (6)	0.1117 (6)	0.7766 (5)	0.0308 (13)
C3	1.1673 (7)	0.0513 (6)	0.8416 (6)	0.0407 (16)
H3	1.2371	0.0040	0.8132	0.049*
C4	1.1762 (8)	0.0635 (7)	0.9504 (6)	0.0465 (18)
C5	1.0753 (7)	0.1320 (6)	0.9960 (6)	0.0423 (16)
H5	1.0841	0.1378	1.0694	0.051*
C6	0.9615 (7)	0.1914 (7)	0.9309 (6)	0.0419 (16)
C7	0.9488 (7)	0.1835 (6)	0.8200 (6)	0.0374 (15)
H7	0.8723	0.2261	0.7755	0.045*
C8	0.8451 (9)	0.2616 (8)	0.9788 (7)	0.057 (2)
C9	0.5970 (6)	0.1875 (6)	0.3097 (5)	0.0292 (13)
C10	0.4627 (6)	0.2185 (5)	0.2498 (5)	0.0270 (12)
C11	0.4353 (6)	0.3072 (6)	0.1421 (5)	0.0321 (13)
H11	0.5013	0.3440	0.0995	0.039*
C12	0.3063 (6)	0.3388 (6)	0.1007 (5)	0.0328 (14)
C13	0.2038 (6)	0.2870 (6)	0.1622 (5)	0.0314 (13)
H13	0.1169	0.3128	0.1331	0.038*
C14	0.2355 (6)	0.1959 (5)	0.2679 (5)	0.0256 (12)
C15	0.3643 (6)	0.1606 (5)	0.3105 (5)	0.0279 (12)
H15	0.3858	0.0976	0.3804	0.033*
C17	0.5715 (9)	0.1824 (8)	0.6347 (8)	0.061 (2)
H17	0.5663	0.1088	0.6280	0.073*
C18	0.4954 (10)	0.2208 (11)	0.7209 (9)	0.085 (4)
H18	0.4424	0.1727	0.7704	0.103*
C19	0.4993 (10)	0.3254 (11)	0.7313 (9)	0.081 (3)
H19	0.4484	0.3519	0.7878	0.097*
C20	0.5823 (9)	0.3984 (9)	0.6552 (8)	0.064 (3)
C21	0.5923 (12)	0.5114 (12)	0.6605 (11)	0.091 (4)
H21	0.5419	0.5420	0.7148	0.109*
C22	0.6719 (14)	0.5746 (11)	0.5897 (12)	0.096 (4)
H22	0.6781	0.6476	0.5973	0.115*
C23	0.7507 (11)	0.5337 (9)	0.4998 (10)	0.074 (3)
C24	0.8317 (13)	0.5984 (10)	0.4198 (12)	0.095 (4)
H24	0.8409	0.6722	0.4234	0.114*
C25	0.8966 (12)	0.5558 (9)	0.3378 (11)	0.088 (3)
H25	0.9508	0.5991	0.2843	0.106*
C26	0.8809 (9)	0.4432 (7)	0.3339 (8)	0.057 (2)
H26	0.9240	0.4151	0.2753	0.068*
C27	0.7400 (8)	0.4227 (7)	0.4915 (7)	0.0451 (18)
C28	0.6557 (7)	0.3526 (7)	0.5716 (6)	0.0447 (18)
Gd1	0.82752 (3)	0.14792 (3)	0.44144 (2)	0.02604 (13)
N1	1.2997 (8)	−0.0016 (8)	1.0209 (7)	0.072 (2)
N2	0.2724 (6)	0.4320 (6)	−0.0147 (5)	0.0500 (16)
N3	0.6506 (6)	0.2452 (5)	0.5622 (5)	0.0448 (15)
N4	0.8089 (6)	0.3768 (5)	0.4088 (5)	0.0414 (14)
O1	0.9505 (5)	0.1690 (4)	0.5913 (4)	0.0412 (11)
O2	1.1124 (5)	0.0033 (5)	0.6459 (4)	0.0466 (12)
O3	1.3864 (8)	−0.0642 (9)	0.9807 (8)	0.118 (4)
O4	1.3055 (9)	0.0089 (8)	1.1154 (7)	0.113 (3)
O5	0.8641 (6)	0.2486 (6)	1.0881 (5)	0.0647 (16)
H5A	0.7931	0.2735	1.1164	0.097*
O6	0.7481 (8)	0.3226 (11)	0.9241 (7)	0.140 (5)
O7	0.6825 (4)	0.2498 (4)	0.2637 (4)	0.0335 (10)
O8	0.6158 (4)	0.1067 (4)	0.4063 (4)	0.0413 (11)
O9	0.3605 (6)	0.4789 (5)	−0.0694 (5)	0.0593 (15)
O10	0.1591 (7)	0.4607 (8)	−0.0498 (6)	0.103 (3)
C16	0.1297 (6)	0.1363 (6)	0.3374 (5)	0.0300 (13)
O11	0.0114 (4)	0.1968 (4)	0.3252 (4)	0.0421 (11)
O12	0.1665 (5)	0.0297 (4)	0.4038 (4)	0.0448 (12)

	U11	U22	U33	U12	U13	U23
C1	0.038 (4)	0.044 (4)	0.022 (3)	−0.013 (3)	−0.002 (3)	−0.014 (3)
C2	0.039 (4)	0.037 (3)	0.020 (3)	−0.010 (3)	−0.004 (3)	−0.012 (3)
C3	0.039 (4)	0.048 (4)	0.032 (4)	−0.001 (3)	−0.007 (3)	−0.013 (3)
C4	0.047 (4)	0.059 (5)	0.030 (4)	−0.007 (3)	−0.014 (3)	−0.010 (3)
C5	0.055 (4)	0.052 (4)	0.023 (3)	−0.011 (3)	−0.004 (3)	−0.016 (3)
C6	0.049 (4)	0.053 (4)	0.025 (4)	−0.010 (3)	0.001 (3)	−0.016 (3)
C7	0.043 (4)	0.052 (4)	0.020 (3)	−0.010 (3)	−0.002 (3)	−0.014 (3)
C8	0.055 (5)	0.080 (6)	0.041 (5)	0.001 (4)	0.000 (4)	−0.038 (4)
C9	0.019 (3)	0.044 (4)	0.024 (3)	−0.006 (2)	−0.001 (2)	−0.012 (3)
C10	0.020 (3)	0.039 (3)	0.021 (3)	−0.005 (2)	0.000 (2)	−0.009 (3)
C11	0.025 (3)	0.045 (4)	0.024 (3)	−0.011 (3)	0.004 (2)	−0.006 (3)
C12	0.038 (4)	0.041 (3)	0.017 (3)	−0.015 (3)	0.000 (3)	−0.002 (3)
C13	0.024 (3)	0.046 (4)	0.024 (3)	−0.007 (3)	−0.001 (2)	−0.011 (3)
C14	0.023 (3)	0.035 (3)	0.019 (3)	−0.008 (2)	0.001 (2)	−0.008 (2)
C15	0.027 (3)	0.036 (3)	0.019 (3)	−0.006 (2)	−0.002 (2)	−0.006 (3)
C17	0.054 (5)	0.060 (5)	0.057 (6)	−0.004 (4)	0.025 (4)	−0.014 (4)
C18	0.073 (7)	0.093 (8)	0.062 (7)	0.011 (6)	0.037 (5)	−0.014 (6)
C19	0.070 (7)	0.101 (8)	0.052 (6)	0.010 (6)	0.029 (5)	−0.024 (6)
C20	0.065 (6)	0.072 (6)	0.053 (5)	0.019 (4)	−0.007 (4)	−0.039 (5)
C21	0.084 (8)	0.117 (10)	0.088 (9)	−0.001 (7)	0.008 (7)	−0.071 (8)
C22	0.113 (10)	0.080 (7)	0.116 (10)	0.008 (7)	−0.021 (8)	−0.075 (8)
C23	0.089 (7)	0.057 (5)	0.079 (7)	−0.002 (5)	−0.022 (6)	−0.033 (5)
C24	0.114 (10)	0.056 (6)	0.128 (11)	−0.026 (6)	−0.008 (8)	−0.039 (7)
C25	0.106 (9)	0.049 (5)	0.099 (9)	−0.029 (5)	0.006 (7)	−0.004 (6)
C26	0.072 (6)	0.041 (4)	0.050 (5)	−0.014 (4)	0.002 (4)	−0.006 (4)
C27	0.047 (4)	0.041 (4)	0.047 (5)	0.002 (3)	−0.015 (4)	−0.019 (3)
C28	0.038 (4)	0.054 (5)	0.036 (4)	0.004 (3)	−0.005 (3)	−0.017 (4)
Gd1	0.02026 (18)	0.0381 (2)	0.01841 (18)	−0.00571 (12)	0.00062 (11)	−0.00808 (13)
N1	0.068 (5)	0.094 (6)	0.053 (5)	0.011 (4)	−0.035 (4)	−0.034 (4)
N2	0.049 (4)	0.065 (4)	0.023 (3)	−0.016 (3)	−0.006 (3)	0.006 (3)
N3	0.041 (3)	0.051 (4)	0.036 (3)	0.003 (3)	0.011 (3)	−0.017 (3)
N4	0.046 (3)	0.042 (3)	0.030 (3)	−0.004 (3)	−0.002 (3)	−0.007 (3)
O1	0.052 (3)	0.048 (3)	0.026 (2)	−0.009 (2)	−0.013 (2)	−0.014 (2)
O2	0.043 (3)	0.059 (3)	0.046 (3)	−0.004 (2)	−0.002 (2)	−0.031 (3)
O3	0.082 (5)	0.163 (8)	0.098 (6)	0.055 (6)	−0.056 (5)	−0.072 (6)
O4	0.113 (6)	0.153 (8)	0.066 (5)	0.039 (6)	−0.060 (5)	−0.058 (5)
O5	0.060 (4)	0.104 (5)	0.033 (3)	−0.009 (3)	0.009 (3)	−0.035 (3)
O6	0.092 (6)	0.236 (11)	0.086 (6)	0.077 (7)	−0.041 (5)	−0.112 (7)
O7	0.027 (2)	0.044 (2)	0.024 (2)	−0.0110 (18)	−0.0016 (18)	−0.0002 (19)
O8	0.026 (2)	0.056 (3)	0.030 (3)	−0.014 (2)	−0.0062 (19)	0.006 (2)
O9	0.060 (4)	0.069 (4)	0.031 (3)	−0.023 (3)	0.008 (3)	0.012 (3)
O10	0.065 (5)	0.137 (7)	0.063 (5)	−0.040 (4)	−0.032 (4)	0.044 (4)
C16	0.032 (3)	0.045 (4)	0.014 (3)	−0.013 (3)	0.001 (2)	−0.009 (3)
O11	0.026 (2)	0.056 (3)	0.040 (3)	−0.012 (2)	0.008 (2)	−0.010 (2)
O12	0.040 (3)	0.054 (3)	0.032 (3)	−0.021 (2)	−0.005 (2)	0.004 (2)

C1—O2	1.242 (8)	C19—H19	0.9300
C1—O1	1.256 (8)	C20—C28	1.405 (10)
C1—C2	1.500 (8)	C20—C21	1.411 (16)
C2—C3	1.390 (9)	C21—C22	1.322 (18)
C2—C7	1.391 (9)	C21—H21	0.9300
C3—C4	1.390 (10)	C22—C23	1.463 (16)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.374 (10)	C23—C24	1.391 (16)
C4—N1	1.487 (10)	C23—C27	1.402 (12)
C5—C6	1.370 (10)	C24—C25	1.338 (16)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.399 (9)	C25—C26	1.417 (13)
C6—C8	1.498 (10)	C25—H25	0.9300
C7—H7	0.9300	C26—N4	1.309 (10)
C8—O6	1.187 (10)	C26—H26	0.9300
C8—O5	1.308 (9)	C27—N4	1.380 (9)
C9—O8	1.243 (8)	C27—C28	1.445 (11)
C9—O7	1.268 (7)	C28—N3	1.348 (9)
C9—C10	1.519 (8)	Gd1—O12i	2.322 (5)
C10—C11	1.383 (9)	Gd1—O2ii	2.342 (4)
C10—C15	1.392 (8)	Gd1—O11iii	2.349 (4)
C11—C12	1.376 (9)	Gd1—O1	2.403 (4)
C11—H11	0.9300	Gd1—O8	2.442 (4)
C12—C13	1.396 (9)	Gd1—O7	2.499 (4)
C12—N2	1.479 (8)	Gd1—N3	2.571 (5)
C13—C14	1.383 (9)	Gd1—N4	2.611 (6)
C13—H13	0.9300	N1—O4	1.204 (9)
C14—C15	1.378 (8)	N1—O3	1.214 (10)
C14—C16	1.498 (8)	N2—O10	1.204 (9)
C15—H15	0.9300	N2—O9	1.220 (8)
C17—N3	1.324 (11)	O2—Gd1ii	2.342 (4)
C17—C18	1.401 (12)	O5—H5A	0.8200
C17—H17	0.9300	C16—O12	1.252 (8)
C18—C19	1.316 (16)	C16—O11	1.257 (7)
C18—H18	0.9300	O11—Gd1iv	2.349 (4)
C19—C20	1.434 (15)	O12—Gd1i	2.322 (5)
O2—C1—O1	125.4 (6)	C25—C24—C23	120.8 (10)
O2—C1—C2	116.8 (6)	C25—C24—H24	119.6
O1—C1—C2	117.8 (6)	C23—C24—H24	119.6
C3—C2—C7	120.1 (6)	C24—C25—C26	118.6 (10)
C3—C2—C1	118.6 (6)	C24—C25—H25	120.7
C7—C2—C1	121.3 (6)	C26—C25—H25	120.7
C4—C3—C2	118.1 (6)	N4—C26—C25	123.3 (9)
C4—C3—H3	121.0	N4—C26—H26	118.3
C2—C3—H3	121.0	C25—C26—H26	118.3
C5—C4—C3	122.9 (7)	N4—C27—C23	121.9 (9)
C5—C4—N1	118.7 (6)	N4—C27—C28	118.2 (6)
C3—C4—N1	118.4 (7)	C23—C27—C28	119.9 (8)
C6—C5—C4	118.5 (6)	N3—C28—C20	122.7 (8)
C6—C5—H5	120.8	N3—C28—C27	118.0 (6)
C4—C5—H5	120.8	C20—C28—C27	119.4 (8)
C5—C6—C7	120.7 (7)	O12i—Gd1—O2ii	76.27 (19)
C5—C6—C8	120.9 (6)	O12i—Gd1—O11iii	124.82 (17)
C7—C6—C8	118.3 (7)	O2ii—Gd1—O11iii	76.07 (18)
C2—C7—C6	119.7 (6)	O12i—Gd1—O1	75.73 (17)
C2—C7—H7	120.1	O2ii—Gd1—O1	126.15 (17)
C6—C7—H7	120.1	O11iii—Gd1—O1	83.73 (17)
O6—C8—O5	124.0 (7)	O12i—Gd1—O8	80.85 (15)
O6—C8—C6	124.2 (7)	O2ii—Gd1—O8	75.42 (17)
O5—C8—C6	111.8 (7)	O11iii—Gd1—O8	134.60 (16)
O8—C9—O7	122.3 (5)	O1—Gd1—O8	141.63 (17)
O8—C9—C10	118.4 (5)	O12i—Gd1—O7	132.49 (15)
O7—C9—C10	119.1 (5)	O2ii—Gd1—O7	81.73 (16)
C11—C10—C15	120.8 (5)	O11iii—Gd1—O7	88.64 (15)
C11—C10—C9	121.4 (5)	O1—Gd1—O7	147.63 (16)
C15—C10—C9	117.6 (5)	O8—Gd1—O7	52.84 (14)
C12—C11—C10	117.3 (6)	O12i—Gd1—N3	84.99 (19)
C12—C11—H11	121.4	O2ii—Gd1—N3	145.6 (2)
C10—C11—H11	121.4	O11iii—Gd1—N3	137.47 (19)
C11—C12—C13	123.4 (6)	O1—Gd1—N3	74.72 (18)
C11—C12—N2	119.3 (6)	O8—Gd1—N3	73.32 (19)
C13—C12—N2	117.3 (6)	O7—Gd1—N3	90.53 (17)
C14—C13—C12	117.9 (6)	O12i—Gd1—N4	138.41 (18)
C14—C13—H13	121.1	O2ii—Gd1—N4	144.26 (19)
C12—C13—H13	121.1	O11iii—Gd1—N4	74.83 (18)
C15—C14—C13	120.1 (5)	O1—Gd1—N4	70.35 (17)
C15—C14—C16	119.7 (5)	O8—Gd1—N4	112.27 (17)
C13—C14—C16	120.2 (5)	O7—Gd1—N4	77.29 (16)
C14—C15—C10	120.5 (6)	N3—Gd1—N4	63.6 (2)
C14—C15—H15	119.8	O4—N1—O3	124.4 (8)
C10—C15—H15	119.8	O4—N1—C4	117.7 (8)
N3—C17—C18	123.5 (10)	O3—N1—C4	117.9 (7)
N3—C17—H17	118.2	O10—N2—O9	122.6 (6)
C18—C17—H17	118.2	O10—N2—C12	119.1 (6)
C19—C18—C17	119.6 (10)	O9—N2—C12	118.3 (6)
C19—C18—H18	120.2	C17—N3—C28	117.6 (6)
C17—C18—H18	120.2	C17—N3—Gd1	121.2 (5)
C18—C19—C20	119.8 (8)	C28—N3—Gd1	119.7 (5)
C18—C19—H19	120.1	C26—N4—C27	117.6 (7)
C20—C19—H19	120.1	C26—N4—Gd1	124.1 (5)
C28—C20—C21	119.8 (10)	C27—N4—Gd1	116.9 (5)
C28—C20—C19	116.8 (9)	C1—O1—Gd1	130.5 (4)
C21—C20—C19	123.4 (9)	C1—O2—Gd1ii	153.7 (4)
C22—C21—C20	121.3 (10)	C8—O5—H5A	109.5
C22—C21—H21	119.4	C9—O7—Gd1	90.7 (3)
C20—C21—H21	119.4	C9—O8—Gd1	94.0 (4)
C21—C22—C23	122.2 (10)	O12—C16—O11	124.9 (6)
C21—C22—H22	118.9	O12—C16—C14	117.3 (5)
C23—C22—H22	118.9	O11—C16—C14	117.8 (6)
C24—C23—C27	117.7 (10)	C16—O11—Gd1iv	127.2 (4)
C24—C23—C22	124.9 (10)	C16—O12—Gd1i	161.3 (4)
C27—C23—C22	117.4 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O7v	0.82	2.03	2.737 (7)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O7i	0.82	2.03	2.737 (7)	145

Symmetry code: (i) .