Poly[(μ-2-acet­oxy­benzoato)(2-acet­oxy­benzoato)-μ-aqua-mercury(II)]

PrakashaReddy, J.

doi:10.1107/S1600536811029278

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1151

doi:10.1107/S1600536811029278

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Poly[(μ-2-acetoxybenzoato)(2-acetoxybenzoato)-μ-aqua-mercury(II)]

J. PrakashaReddy ^a ^*

^aDepartment of Chemistry, MS015, Brandeis University, Waltham, MA 02454, USA
^*Correspondence e-mail: j.prakashareddy@gmail.com

(Received 28 June 2011; accepted 20 July 2011; online 30 July 2011)

In the title compound, [Hg(C₉H₇O₄)₂(H₂O)]_n, the Hg^II ion is five-coordinated by three acetylsalicylate anions and water leading to the formation of a coordination polymer extending parallel to (001). O—H⋯O and C—H⋯O hydrogen bonds are effective in the stabilization of the crystal structure.

Related literature

For general background to metal complexes with acetylsalicylate as a ligand, see: Manojlović-Muir (1973 ); Garcia et al. (2003 ); Greenaway et al. (1984 ); Fujimori et al. (2005 ); James et al. (1998 ); Vasquez-Arciga et al. (2004); Ma & Moulton (2007 ).

Experimental

Crystal data

[Hg(C₉H₇O₄)₂(H₂O)]
M_r = 1153.80
Triclinic, $[P \overline 1]$
a = 6.1851 (9) Å
b = 10.1359 (17) Å
c = 15.453 (2) Å
α = 100.308 (7)°
β = 98.700 (8)°
γ = 100.667 (7)°
V = 919.5 (2) Å³
Z = 1
Mo Kα radiation
μ = 8.42 mm⁻¹
T = 120 K
0.21 × 0.17 × 0.02 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: analytical (De Meulenaer & Tompa, 1965 ) T_min = 0.24, T_max = 0.83
9510 measured reflections
5293 independent reflections
4404 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.092
S = 0.97
5293 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 1.88 e Å⁻³
Δρ_min = −2.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H2⋯O2ⁱ	0.82	2.01	2.835 (7)	180 (1)
O9—H1⋯O5ⁱ	0.82	1.93	2.758 (5)	179 (1)
C9—H92⋯O1ⁱⁱ	0.95	2.49	3.409 (9)	163
C15—H151⋯O4ⁱⁱⁱ	0.95	2.51	3.221 (8)	132
C18—H181⋯O5ⁱⁱⁱ	0.95	2.59	3.530 (9)	169
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029278/dn2701sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029278/dn2701Isup2.hkl

checkCIF report

Comment top

First crystal structure of copper and acetylsalicylic acid (ASA) metal complex was reported by Manojlović-Muir (1973) which was reinvestigated by Garcia et al. (2003). Various other metal complexes of ASA have been also reported (Greenaway et al., 1984; Fujimori et al., 2005; James et al., 1998; Ma & Moulton, 2007; Vásquez-Árciga et al., 2004). For further investigation of the ASA complexes, we synthesized the title compound.

The asymmetric unit of the title compound contains two molecules of ASA, and a bridging water molecule coordinated to the Hg^II ion. The molecular arrangement around Hg^II is shown in Fig. 1. Crystal structure analysis shows that the carboxylate of the ASA molecules interacts with Hg^II in a monodentate fashion while acetyl group O atom of one of the ASA molecules coordinated to Hg^II ion forming a coordination polymer. The uncoordinated O atom of the carboxylate form intermolecular O—H···O hydrogen bonds with bridging water molecule resulting in the build up of a two-dimensional network parallel to the (001) plane (Fig. 2 and Table 1). Within this layer exist also weak C—H···O interactions (Table 1).

Related literature top

For general background to metal complexes with aspirin as a ligand, see: Manojlović-Muir (1973); Garcia et al. (2003); Greenaway et al. (1984); Fujimori et al.(2005); James et al. (1998); Vasquez-Arciga et al. (2004); Ma & Moulton (2007).

Experimental top

The title compound was synthesized by adding a solution of acetylsalicylic acid (36 mg, 0.2 mmol) dissolved in methanol (5 ml) to a mercuric chloride (27 mg, 0.1 mmol) dissolved in methanol (5 ml) in a 2:1 ratio respectively. After 3–4 days, colourless crystals of the title compound were obtained on slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. The title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry codes: (i) 2 - x, 1 - y, 1 - z; (ii) 2 - x, 2 - y, 1 - z; (iii) 1 + x,y,z
	Fig. 2. Packing diagram of the title compound. Hydrogen-bond interactions are drawn with dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

Poly[(µ-2-acetoxybenzoato)(2-acetoxybenzoato)-µ-aqua-mercury(II)] top

Crystal data top

[Hg(C₉H₇O₄)₂(H₂O)]	Z = 1
M_r = 1153.80	F(000) = 552
Triclinic, P1	D_x = 2.084 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1851 (9) Å	Cell parameters from 3872 reflections
b = 10.1359 (17) Å	θ = 3–30°
c = 15.453 (2) Å	µ = 8.42 mm⁻¹
α = 100.308 (7)°	T = 120 K
β = 98.700 (8)°	Plate, colorless
γ = 100.667 (7)°	0.21 × 0.17 × 0.02 mm
V = 919.5 (2) Å³

Data collection top

Bruker Kappa APEXII diffractometer	4404 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ & ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: analytical (De Meulenaer & Tompa, 1965)	h = −8→7
T_min = 0.24, T_max = 0.83	k = −14→13
9510 measured reflections	l = −21→21
5293 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.092	Method = Modified Sheldrick w = 1/[σ²(F²) + (0.04P)² + 6.15P], where P = [max(F_o²,0) + 2F_c²]/3
S = 0.97	(Δ/σ)_max = 0.001
5293 reflections	Δρ_max = 1.88 e Å⁻³
253 parameters	Δρ_min = −2.19 e Å⁻³
0 restraints

Crystal data top

[Hg(C₉H₇O₄)₂(H₂O)]	γ = 100.667 (7)°
M_r = 1153.80	V = 919.5 (2) Å³
Triclinic, P1	Z = 1
a = 6.1851 (9) Å	Mo Kα radiation
b = 10.1359 (17) Å	µ = 8.42 mm⁻¹
c = 15.453 (2) Å	T = 120 K
α = 100.308 (7)°	0.21 × 0.17 × 0.02 mm
β = 98.700 (8)°

Data collection top

Bruker Kappa APEXII diffractometer	5293 independent reflections
Absorption correction: analytical (De Meulenaer & Tompa, 1965)	4404 reflections with I > 2σ(I)
T_min = 0.24, T_max = 0.83	R_int = 0.037
9510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 0.97	Δρ_max = 1.88 e Å⁻³
5293 reflections	Δρ_min = −2.19 e Å⁻³
253 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Hg1	0.89515 (4)	0.65817 (2)	0.467447 (16)	0.0168
O1	0.8495 (8)	0.5346 (4)	0.3440 (3)	0.0248
O2	0.4800 (8)	0.5246 (5)	0.3271 (3)	0.0285
O3	0.2895 (7)	0.4772 (4)	0.1441 (3)	0.0215
O4	0.5203 (8)	0.6855 (4)	0.1796 (4)	0.0281
O5	0.6204 (8)	0.7673 (5)	0.5843 (3)	0.0270
O6	0.9879 (7)	0.7872 (4)	0.5911 (3)	0.0222
O7	1.2498 (7)	1.0048 (4)	0.7117 (3)	0.0174
O8	1.0778 (8)	1.1274 (5)	0.6272 (3)	0.0268
O9	1.2672 (7)	0.5721 (4)	0.4763 (3)	0.0198
C1	0.6439 (11)	0.4964 (6)	0.2984 (4)	0.0198
C2	0.6323 (10)	0.4156 (6)	0.2068 (4)	0.0165
C3	0.7982 (11)	0.3423 (6)	0.1913 (4)	0.0205
C4	0.7977 (11)	0.2696 (6)	0.1066 (5)	0.0231
C5	0.6320 (11)	0.2710 (6)	0.0339 (5)	0.0249
C6	0.4648 (11)	0.3435 (6)	0.0472 (4)	0.0216
C7	0.4668 (10)	0.4133 (6)	0.1336 (4)	0.0178
C8	0.3385 (11)	0.6172 (6)	0.1734 (4)	0.0207
C9	0.1367 (13)	0.6643 (7)	0.1952 (6)	0.0365
C10	0.8163 (11)	0.8122 (6)	0.6245 (4)	0.0195
C11	0.8677 (10)	0.8985 (5)	0.7175 (4)	0.0171
C12	0.7009 (11)	0.8886 (6)	0.7696 (5)	0.0223
C13	0.7399 (12)	0.9606 (6)	0.8567 (4)	0.0238
C14	0.9507 (11)	1.0455 (6)	0.8963 (4)	0.0227
C15	1.1151 (11)	1.0597 (6)	0.8456 (4)	0.0204
C16	1.0744 (10)	0.9876 (6)	0.7573 (4)	0.0174
C17	1.2367 (11)	1.0780 (6)	0.6470 (4)	0.0224
C18	1.4387 (13)	1.0861 (8)	0.6063 (5)	0.0333
H31	0.9129	0.3424	0.2398	0.0255*
H41	0.9097	0.2185	0.0975	0.0281*
H51	0.6341	0.2225	−0.0244	0.0287*
H61	0.3524	0.3452	−0.0016	0.0251*
H91	0.1725	0.7613	0.2154	0.0468*
H92	0.0862	0.6224	0.2410	0.0468*
H93	0.0218	0.6394	0.1432	0.0468*
H121	0.5576	0.8309	0.7441	0.0281*
H131	0.6235	0.9526	0.8904	0.0321*
H141	0.9795	1.0926	0.9572	0.0282*
H151	1.2569	1.1192	0.8710	0.0242*
H181	1.4269	1.1379	0.5610	0.0441*
H182	1.5677	1.1294	0.6511	0.0441*
H183	1.4512	0.9960	0.5807	0.0441*
H2	1.3284	0.5582	0.4330	0.0237*
H1	1.3720	0.6302	0.5086	0.0237*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.01839 (11)	0.01710 (10)	0.01515 (12)	0.00792 (7)	0.00211 (8)	0.00097 (7)
O1	0.028 (2)	0.025 (2)	0.021 (2)	0.0116 (18)	0.0052 (19)	−0.0016 (18)
O2	0.027 (3)	0.042 (3)	0.022 (2)	0.018 (2)	0.007 (2)	0.005 (2)
O3	0.015 (2)	0.022 (2)	0.028 (3)	0.0090 (16)	0.0011 (18)	0.0050 (18)
O4	0.026 (2)	0.021 (2)	0.040 (3)	0.0077 (18)	0.012 (2)	0.009 (2)
O5	0.024 (2)	0.029 (2)	0.026 (3)	0.0072 (18)	−0.002 (2)	0.0028 (19)
O6	0.022 (2)	0.025 (2)	0.017 (2)	0.0076 (17)	0.0018 (18)	−0.0020 (17)
O7	0.020 (2)	0.0172 (18)	0.019 (2)	0.0097 (15)	0.0057 (17)	0.0068 (16)
O8	0.032 (3)	0.029 (2)	0.027 (3)	0.0148 (19)	0.008 (2)	0.015 (2)
O9	0.021 (2)	0.023 (2)	0.014 (2)	0.0036 (16)	0.0030 (17)	0.0014 (16)
C1	0.025 (3)	0.020 (3)	0.017 (3)	0.007 (2)	0.005 (2)	0.008 (2)
C2	0.014 (3)	0.019 (3)	0.018 (3)	0.005 (2)	0.002 (2)	0.006 (2)
C3	0.026 (3)	0.020 (3)	0.018 (3)	0.009 (2)	0.004 (3)	0.007 (2)
C4	0.024 (3)	0.020 (3)	0.026 (4)	0.008 (2)	0.009 (3)	0.002 (2)
C5	0.029 (3)	0.024 (3)	0.020 (3)	0.004 (2)	0.005 (3)	−0.001 (2)
C6	0.022 (3)	0.022 (3)	0.019 (3)	0.005 (2)	−0.001 (2)	0.003 (2)
C7	0.016 (3)	0.015 (2)	0.022 (3)	0.003 (2)	0.002 (2)	0.004 (2)
C8	0.025 (3)	0.019 (3)	0.022 (3)	0.009 (2)	0.006 (3)	0.012 (2)
C9	0.031 (4)	0.029 (3)	0.056 (5)	0.015 (3)	0.013 (4)	0.016 (3)
C10	0.025 (3)	0.015 (2)	0.021 (3)	0.008 (2)	0.005 (2)	0.005 (2)
C11	0.017 (3)	0.012 (2)	0.021 (3)	0.006 (2)	−0.001 (2)	0.001 (2)
C12	0.021 (3)	0.022 (3)	0.027 (4)	0.006 (2)	0.008 (3)	0.009 (3)
C13	0.034 (4)	0.026 (3)	0.020 (3)	0.015 (3)	0.014 (3)	0.013 (3)
C14	0.032 (4)	0.023 (3)	0.016 (3)	0.013 (3)	0.003 (3)	0.004 (2)
C15	0.024 (3)	0.016 (2)	0.021 (3)	0.005 (2)	0.002 (2)	0.003 (2)
C16	0.019 (3)	0.018 (2)	0.019 (3)	0.011 (2)	0.003 (2)	0.005 (2)
C17	0.028 (3)	0.018 (3)	0.023 (3)	0.007 (2)	0.003 (3)	0.007 (2)
C18	0.036 (4)	0.041 (4)	0.034 (4)	0.013 (3)	0.019 (3)	0.020 (3)

Geometric parameters (Å, º) top

Hg1—O9ⁱ	2.708 (4)	C5—C6	1.394 (9)
Hg1—O8ⁱⁱ	2.823 (4)	C5—H51	0.950
Hg1—O1	2.034 (4)	C6—C7	1.393 (9)
Hg1—O6	2.046 (4)	C6—H61	0.950
Hg1—O9	2.601 (4)	C8—C9	1.479 (10)
O1—C1	1.309 (8)	C9—H91	0.950
O2—C1	1.226 (8)	C9—H92	0.950
O3—C7	1.388 (7)	C9—H93	0.950
O3—C8	1.372 (7)	C10—C11	1.497 (8)
O4—C8	1.187 (8)	C11—C12	1.402 (9)
O5—C10	1.236 (8)	C11—C16	1.401 (8)
O6—C10	1.295 (7)	C12—C13	1.373 (9)
O7—C16	1.382 (7)	C12—H121	0.950
O7—C17	1.348 (8)	C13—C14	1.403 (9)
O8—C17	1.207 (8)	C13—H131	0.950
O9—H2	0.820	C14—C15	1.377 (9)
O9—H1	0.820	C14—H141	0.950
C1—C2	1.488 (9)	C15—C16	1.389 (9)
C2—C3	1.398 (8)	C15—H151	0.950
C2—C7	1.400 (8)	C17—C18	1.477 (10)
C3—C4	1.382 (9)	C18—H181	0.950
C3—H31	0.950	C18—H182	0.950
C4—C5	1.406 (10)	C18—H183	0.950
C4—H41	0.950

O9—Hg1—O8	107.12 (11)	O4—C8—O3	121.8 (5)
O9—Hg1—O6	94.68 (16)	O4—C8—C9	127.9 (5)
O1—Hg1—O6	171.97 (18)	O3—C8—C9	110.3 (5)
O1—Hg1—O9	78.28 (14)	O5—C10—C11	121.1 (5)
C1—O1—Hg1	116.6 (3)	O6—C10—C11	116.1 (5)
C8—O3—C7	118.1 (4)	C12—C11—C16	117.2 (5)
C17—O7—C16	117.7 (4)	C12—C11—C10	118.4 (5)
O2—C1—O1	124.4 (5)	C16—C11—C10	124.4 (5)
O2—C1—C2	123.5 (5)	C13—C12—C11	121.9 (5)
O1—C1—C2	112.1 (5)	C12—C13—C14	120.1 (5)
C3—C2—C7	117.5 (5)	C15—C14—C13	118.9 (5)
C3—C2—C1	119.1 (5)	C16—C15—C14	120.2 (5)
C7—C2—C1	123.4 (5)	C15—C16—O7	116.4 (5)
C4—C3—C2	121.0 (5)	C15—C16—C11	121.6 (5)
C5—C4—C3	120.1 (5)	O7—C16—C11	122.0 (5)
C4—C5—C6	120.4 (5)	O8—C17—O7	123.1 (5)
C7—C6—C5	118.6 (5)	O8—C17—C18	126.5 (6)
C6—C7—O3	116.2 (5)	O7—C17—C18	110.4 (5)
C6—C7—C2	122.4 (5)	H181—C18—H183	110.00
O3—C7—C2	121.3 (5)	H182—C18—H183	109.00

O9—Hg1—O1—C1	163.5 (4)	C7—O3—C8—O4	9.0 (8)
O9—Hg1—O6—C10	−156.3 (3)	C7—O3—C8—C9	−170.8 (5)
Hg1—O1—C1—O2	−3.7 (7)	Hg1—O6—C10—O5	−3.0 (6)
Hg1—O1—C1—C2	175.2 (3)	Hg1—O6—C10—C11	176.3 (3)
O2—C1—C2—C3	−154.5 (5)	O5—C10—C11—C12	22.0 (8)
O1—C1—C2—C3	26.5 (7)	O6—C10—C11—C12	−157.4 (5)
O2—C1—C2—C7	27.9 (8)	O5—C10—C11—C16	−159.3 (5)
O1—C1—C2—C7	−151.1 (5)	O6—C10—C11—C16	21.3 (7)
C7—C2—C3—C4	−0.3 (8)	C16—C11—C12—C13	−1.9 (8)
C1—C2—C3—C4	−178.0 (5)	C10—C11—C12—C13	176.9 (5)
C2—C3—C4—C5	1.1 (8)	C11—C12—C13—C14	−0.3 (8)
C3—C4—C5—C6	−0.6 (8)	C12—C13—C14—C15	2.8 (8)
C4—C5—C6—C7	−0.5 (8)	C14—C15—C16—O7	−177.9 (5)
C5—C6—C7—O3	−176.4 (4)	C17—O7—C16—C15	−108.1 (5)
C5—C6—C7—C2	1.3 (8)	C17—O7—C16—C11	73.3 (6)
C8—O3—C7—C6	−118.6 (5)	C12—C11—C16—C15	1.8 (7)
C8—O3—C7—C2	63.6 (7)	C10—C11—C16—C15	−177.0 (5)
C3—C2—C7—C6	−0.9 (8)	C12—C11—C16—O7	−179.7 (4)
C1—C2—C7—C6	176.7 (5)	C10—C11—C16—O7	1.5 (7)
C3—C2—C7—O3	176.7 (4)	C16—O7—C17—O8	−0.4 (7)
C1—C2—C7—O3	−5.7 (8)	C16—O7—C17—C18	180.0 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H2···O2ⁱⁱⁱ	0.82	2.01	2.835 (7)	180 (1)
O9—H1···O5ⁱⁱⁱ	0.82	1.93	2.758 (5)	179 (1)
C9—H92···O1^iv	0.95	2.49	3.409 (9)	163
C15—H151···O4ⁱⁱ	0.95	2.51	3.221 (8)	132
C18—H181···O5ⁱⁱ	0.95	2.59	3.530 (9)	169

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

Experimental details

Crystal data
Chemical formula	[Hg(C₉H₇O₄)₂(H₂O)]
M_r	1153.80
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.1851 (9), 10.1359 (17), 15.453 (2)
α, β, γ (°)	100.308 (7), 98.700 (8), 100.667 (7)
V (Å³)	919.5 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	8.42
Crystal size (mm)	0.21 × 0.17 × 0.02

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Analytical (De Meulenaer & Tompa, 1965)
T_min, T_max	0.24, 0.83
No. of measured, independent and observed [I > 2σ(I)] reflections	9510, 5293, 4404
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.092, 0.97
No. of reflections	5293
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.88, −2.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H2···O2ⁱ	0.820	2.010	2.835 (7)	179.5 (3)
O9—H1···O5ⁱ	0.820	1.930	2.758 (5)	179.1 (3)
C9—H92···O1ⁱⁱ	0.95	2.49	3.409 (9)	163
C15—H151···O4ⁱⁱⁱ	0.95	2.51	3.221 (8)	132
C18—H181···O5ⁱⁱⁱ	0.95	2.59	3.530 (9)	169

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

Acknowledgements

The author thank Bruce Foxman for his generous support in providing single-crystal data and valuable suggestions.

References

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