A cuboidal [Cu4(SO4)4] structure supported by β-picoline ligands

Park, A.M.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2056989022000780

Jerry P. Jasinski tribute

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ISSN: 2056-9890

Volume 78| Part 2| February 2022| Pages 108-110

https://doi.org/10.1107/S2056989022000780

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ADDENDA AND ERRATA
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A cuboidal [Cu₄(SO₄)₄] structure supported by β-picoline ligands

Ava M. Park,^a James A. Golen ^b and David R. Manke ^b ^*

^aPortsmouth Abbey School, 285 Cory's Lane, Portsmouth, RI, 02871, USA, and ^bUniversity of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA
^*Correspondence e-mail: dmanke@umassd.edu

Edited by M. Zeller, Purdue University, USA (Received 15 January 2022; accepted 23 January 2022; online 28 January 2022)

The solid-state structure of the cobalt–β-picoline–sulfate complex tetra-μ₃-sulfato-tetrakis[bis(3-methylpyridine)cobalt(II)], [Co₄(SO₄)₄(C₆H₇N)₈], is reported. The tetrameric cobalt cluster contains a cuboidal core comprised of four cobalt(II) cations and four sulfate anions at alternate cube vertices. The cobalt corners are each capped with two β-picoline ligands. The sulfate anions adopt a rare [3.2110] bridging motif, and the cuboidal cluster is unprecedented in coordination chemistry.

Keywords: crystal structure; picoline; sulfate; transition metal; coordination chemistry; cobalt complexes.

CCDC reference: 2143864

1. Chemical context

For the past few years, our lab has examined the solid-state structures of first-row transition-metal–pyridine–sulfate complexes (Park et al., 2019 ; Pham et al., 2018 ; Roy et al., 2018 ). Despite the first such compound being reported in 1886 (Jørgensen, 1886 ; Manke, 2021 ), the structures of only two had been described in the literature when we started exploring this class of compounds. A series of these structures including Fe, Co, Ni, and Zn, showed one-dimensional coordination polymers exhibiting sulfate dianions bridging in μ-sulfato-κ²O:O′ modes. Interestingly, by modifying growth conditions, cobalt demonstrated two additional crystalline forms with variation in the bridging mode of sulfate ions that was not observed for the other metals. We have also explored the structural chemistry of such complexes with substituted pyridines, including γ-picoline, which showed similar structural chemistry to that observed with the pyridine ligand (Pham et al., 2019 ). When we looked at the reaction of cobalt sulfate with β-picoline, a unique structure was obtained, a tetramer exhibiting an unprecedented cuboidal Cu₄(SO₄)₄ core, described herein.

2. Structural commentary

The asymmetric unit of the title compound contains one cobalt cation, one sulfate anion, and two β-picoline ligands (Fig. 1). When grown out, the cobalt center demonstrates a pseudo-octahedral coordination environment. This consists of two β-picoline nitrogen atoms, two oxygen atoms of a chelating sulfate ligand, one oxygen atom of a second sulfate anion, which bridges to another metal, and one terminal oxygen atom of a third sulfate ligand. The grown-out structure forms a tetramer of (β-pic)₂CoSO₄ units, demonstrating a cuboidal core in which four vertices are occupied by cobalt cations, and the other four vertices are occupied by sulfate anions (Fig. 2). The sulfate anions all bridge three Co²⁺ cations, demonstrating [3.2110] bridging by Harris notation (Fig. 3). Harris notation is written as [X·YYYY] where X is the number of metals that a ligand bridges, and the Ys are the number of metals connected to each donor atom in the ligand (Papatriantafyllopoulou et al., 2009 ). The [3.2110] bridging motif is rare in sulfates and has only been observed in 1D coordination polymers of copper (Li et al., 2008 ) and lanthanide/iron mixed-metal 3D coordination polymers (He et al., 2017 ). There are two C—H⋯O interactions between the ortho hydrogens of one β-picoline ligand and the oxygens of two sulfate ions (Table 1). This results in a plane-to-plane angle between the CoN₃O plane and the pyridine ring of 16.25 (9)°. These interactions are not present in the second unique picoline ligand, giving a larger plane-to-plane angle of 26.95 (9)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4ⁱ	0.93	2.53	3.116 (4)	121
C3—H3⋯O2ⁱⁱ	0.93	2.46	3.135 (4)	129
C5—H5⋯O1	0.93	2.49	3.070 (4)	121
Symmetry codes: (i) ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The asymmetric unit of the title compound showing the atomic labeling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.

Figure 2
The [3.2110] coordination mode of sulfate in the title compound.

Figure 3
The cuboidal tetramer of the title compound. H atoms have been omitted for clarity.

3. Supramolecular features

The crystal packing for the compound is shown in Fig. 4. The are weak C—H⋯O interactions between the trans-hydrogen atom of one picoline ligand and one of the terminal sulfate oxygens of a neighboring cuboid [C3—H3⋯O2ⁱⁱ; symmetry code: (ii) $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z, Table 1). This interaction might assist in the interdigitation of the cuboids in the structure. No significant π–π interactions are observed.

Figure 4
The crystal packing of the title compound shown along the c axis. H atoms have been omitted for clarity.

4. Database survey

The reported structures demonstrating sulfate ions with [3.2110] bridging modes are with copper (DOHKIV, DOHKIB: Li et al., 2008) or mixtures of lanthanides with iron (He et al., 2017), including dysprosium (DADNOO), erbium (DADPEG), europium (DADNII), gadolinium (DADNUU) and samarium (DADPAC). The prior structures of metal–pyridine sulfate complexes include three variations with pyridine (QIBFOZ: Pham et al., 2018; QOXJAR, QOXJEV: Park et al., 2019) and one with γ-picoline (ROFMIL: Pham et al., 2019), all of which demonstrate 1D coordination polymers that are structurally quite different than the cuboidal compound reported here.

5. Synthesis and crystallization

32 mg of CoSO₄·7H₂O were dissolved in 2.0 mL of 3-methylpyridine (Aldrich) and heated at 343 K for 24 h. Dark-pink crystals suitable for X-ray analysis were obtained.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed in calculated positions [C—H = 0.93 Å (sp²) and 0.96 Å (sp³)]. Isotropic displacement parameters were set to 1.2U_eqC (sp²) or 1.5U_eqC (sp³).

Table 2
Experimental details

Crystal data
Chemical formula	[Co₄(SO₄)₄(C₆H₇N)₈]
M_r	1364.96
Crystal system, space group	Tetragonal, P $[\overline{4}]$ 2₁c
Temperature (K)	298
a, c (Å)	15.6121 (16), 11.8359 (13)
V (Å³)	2884.9 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.35
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker D8 Venture CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2018 )
T_min, T_max	0.517, 0.562
No. of measured, independent and observed [I > 2σ(I)] reflections	54595, 2744, 2624
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.046, 1.14
No. of reflections	2744
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20
Absolute structure	Flack x determined using 1117 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.007 (4)
Computer programs: APEX3 and SAINT (Bruker, 2018), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2143864

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022000780/zl5027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022000780/zl5027Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Tetra-µ₃-sulfato-tetrakis[bis(3-methylpyridine)cobalt(II)] top

Crystal data top

[Co₄(SO₄)₄(C₆H₇N)₈]	D_x = 1.571 Mg m⁻³
M_r = 1364.96	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 9496 reflections
a = 15.6121 (16) Å	θ = 2.9–25.7°
c = 11.8359 (13) Å	µ = 1.35 mm⁻¹
V = 2884.9 (7) Å³	T = 298 K
Z = 2	BLOCK, pink
F(000) = 1400	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	2624 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θ_max = 25.7°, θ_min = 2.9°
T_min = 0.517, T_max = 0.562	h = −19→19
54595 measured reflections	k = −19→19
2744 independent reflections	l = −14→14

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0165P)² + 1.2064P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.019	(Δ/σ)_max = 0.001
wR(F²) = 0.046	Δρ_max = 0.16 e Å⁻³
S = 1.14	Δρ_min = −0.20 e Å⁻³
2744 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
184 parameters	Extinction coefficient: 0.0049 (4)
0 restraints	Absolute structure: Flack x determined using 1117 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.007 (4)

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Co1	0.64636 (2)	0.49053 (2)	0.41389 (3)	0.02066 (11)
S1	0.52522 (4)	0.64004 (4)	0.35520 (5)	0.02043 (15)
O1	0.58168 (12)	0.57205 (12)	0.30908 (15)	0.0267 (4)
O2	0.49144 (15)	0.69145 (13)	0.26473 (17)	0.0370 (5)
O3	0.45605 (11)	0.59894 (11)	0.42553 (16)	0.0240 (4)
O4	0.57304 (12)	0.69234 (11)	0.43961 (15)	0.0258 (4)
N1	0.75982 (14)	0.57112 (15)	0.4121 (2)	0.0319 (5)
N2	0.70169 (16)	0.42286 (15)	0.2775 (2)	0.0293 (5)
C1	0.82170 (19)	0.5691 (2)	0.4896 (3)	0.0400 (7)
H1	0.813680	0.534627	0.552786	0.048*
C2	0.8976 (2)	0.6156 (2)	0.4819 (3)	0.0489 (8)
C3	0.9084 (2)	0.6660 (2)	0.3863 (3)	0.0546 (10)
H3	0.958296	0.697697	0.376688	0.065*
C4	0.8451 (2)	0.6690 (2)	0.3064 (3)	0.0541 (10)
H4	0.851466	0.702977	0.242445	0.065*
C5	0.7719 (2)	0.6210 (2)	0.3218 (3)	0.0434 (8)
H5	0.729157	0.623471	0.267110	0.052*
C6	0.9650 (3)	0.6110 (3)	0.5724 (4)	0.0829 (15)
H6A	0.946445	0.572676	0.630913	0.124*
H6B	0.973938	0.667009	0.603611	0.124*
H6C	1.017567	0.590328	0.540358	0.124*
C7	0.6638 (2)	0.4183 (2)	0.1768 (3)	0.0340 (7)
H7	0.611734	0.446338	0.167140	0.041*
C8	0.6978 (2)	0.3738 (2)	0.0853 (3)	0.0422 (7)
C9	0.7741 (2)	0.3311 (2)	0.1032 (3)	0.0499 (9)
H9	0.798504	0.299413	0.045000	0.060*
C10	0.8143 (2)	0.3351 (2)	0.2062 (3)	0.0490 (9)
H10	0.865907	0.306837	0.218114	0.059*
C11	0.7766 (2)	0.3817 (2)	0.2914 (3)	0.0386 (8)
H11	0.803962	0.384829	0.361126	0.046*
C12	0.6512 (3)	0.3707 (3)	−0.0255 (3)	0.0732 (12)
H12A	0.590895	0.377919	−0.012705	0.110*
H12B	0.661205	0.316328	−0.061099	0.110*
H12C	0.671634	0.415746	−0.073630	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01998 (17)	0.02203 (18)	0.01997 (16)	0.00207 (14)	0.00180 (15)	0.00176 (14)
S1	0.0216 (3)	0.0201 (3)	0.0196 (3)	0.0031 (3)	0.0031 (2)	0.0046 (3)
O1	0.0293 (10)	0.0290 (10)	0.0218 (9)	0.0075 (8)	0.0056 (8)	0.0029 (8)
O2	0.0435 (12)	0.0380 (11)	0.0297 (10)	0.0114 (11)	−0.0007 (10)	0.0133 (9)
O3	0.0227 (9)	0.0272 (9)	0.0223 (9)	−0.0037 (7)	0.0042 (8)	0.0004 (8)
O4	0.0259 (9)	0.0213 (9)	0.0301 (11)	−0.0045 (8)	0.0048 (8)	0.0015 (7)
N1	0.0281 (12)	0.0299 (12)	0.0378 (13)	−0.0040 (10)	0.0080 (12)	0.0009 (12)
N2	0.0305 (12)	0.0272 (12)	0.0301 (13)	0.0033 (11)	0.0070 (11)	0.0008 (11)
C1	0.0349 (16)	0.0417 (17)	0.0434 (18)	−0.0091 (14)	0.0040 (14)	0.0014 (14)
C2	0.0337 (16)	0.051 (2)	0.062 (2)	−0.0128 (14)	0.0054 (17)	−0.0051 (19)
C3	0.0408 (19)	0.043 (2)	0.080 (3)	−0.0156 (16)	0.0191 (18)	0.0026 (18)
C4	0.052 (2)	0.042 (2)	0.068 (3)	−0.0086 (16)	0.019 (2)	0.0151 (18)
C5	0.0396 (18)	0.0437 (19)	0.0470 (19)	−0.0036 (15)	0.0103 (16)	0.0107 (16)
C6	0.048 (2)	0.102 (4)	0.098 (4)	−0.026 (2)	−0.017 (3)	0.002 (3)
C7	0.0376 (17)	0.0333 (15)	0.0310 (15)	−0.0005 (13)	0.0067 (13)	0.0015 (13)
C8	0.061 (2)	0.0340 (16)	0.0314 (15)	−0.0070 (14)	0.0115 (17)	−0.0043 (14)
C9	0.067 (2)	0.0349 (17)	0.048 (2)	0.0039 (16)	0.0277 (18)	−0.0072 (15)
C10	0.047 (2)	0.0364 (18)	0.063 (2)	0.0135 (15)	0.0187 (18)	−0.0001 (16)
C11	0.0369 (18)	0.0342 (17)	0.045 (2)	0.0085 (14)	0.0064 (14)	0.0007 (14)
C12	0.107 (4)	0.076 (3)	0.036 (2)	−0.002 (3)	−0.002 (3)	−0.012 (2)

Geometric parameters (Å, º) top

Co1—S1ⁱ	2.7458 (7)	C3—C4	1.368 (6)
Co1—O1	2.0441 (19)	C4—H4	0.9300
Co1—O3ⁱ	2.2037 (19)	C4—C5	1.379 (5)
Co1—O3ⁱⁱ	2.1274 (18)	C5—H5	0.9300
Co1—O4ⁱ	2.1229 (18)	C6—H6A	0.9600
Co1—N1	2.173 (2)	C6—H6B	0.9600
Co1—N2	2.114 (2)	C6—H6C	0.9600
S1—O1	1.4839 (19)	C7—H7	0.9300
S1—O2	1.438 (2)	C7—C8	1.391 (4)
S1—O3	1.5069 (18)	C8—C9	1.382 (5)
S1—O4	1.491 (2)	C8—C12	1.501 (5)
N1—C1	1.332 (4)	C9—H9	0.9300
N1—C5	1.336 (4)	C9—C10	1.371 (6)
N2—C7	1.333 (4)	C10—H10	0.9300
N2—C11	1.345 (4)	C10—C11	1.376 (5)
C1—H1	0.9300	C11—H11	0.9300
C1—C2	1.392 (4)	C12—H12A	0.9600
C2—C3	1.389 (5)	C12—H12B	0.9600
C2—C6	1.503 (5)	C12—H12C	0.9600
C3—H3	0.9300

O1—Co1—S1ⁱ	129.94 (5)	N1—C1—H1	118.0
O1—Co1—O3ⁱⁱ	94.41 (7)	N1—C1—C2	124.0 (3)
O1—Co1—O3ⁱ	97.00 (7)	C2—C1—H1	118.0
O1—Co1—O4ⁱ	162.52 (7)	C1—C2—C6	121.6 (4)
O1—Co1—N1	92.08 (9)	C3—C2—C1	116.9 (3)
O1—Co1—N2	92.84 (9)	C3—C2—C6	121.5 (3)
O3ⁱ—Co1—S1ⁱ	33.21 (5)	C2—C3—H3	120.2
O3ⁱⁱ—Co1—S1ⁱ	81.36 (5)	C4—C3—C2	119.7 (3)
O3ⁱⁱ—Co1—O3ⁱ	86.57 (8)	C4—C3—H3	120.2
O3ⁱⁱ—Co1—N1	173.44 (9)	C3—C4—H4	120.4
O4ⁱ—Co1—S1ⁱ	32.58 (5)	C3—C4—C5	119.3 (3)
O4ⁱ—Co1—O3ⁱⁱ	83.94 (7)	C5—C4—H4	120.4
O4ⁱ—Co1—O3ⁱ	65.55 (7)	N1—C5—C4	122.6 (4)
O4ⁱ—Co1—N1	90.16 (9)	N1—C5—H5	118.7
N1—Co1—S1ⁱ	95.20 (8)	C4—C5—H5	118.7
N1—Co1—O3ⁱ	93.61 (8)	C2—C6—H6A	109.5
N2—Co1—S1ⁱ	136.90 (7)	C2—C6—H6B	109.5
N2—Co1—O3ⁱ	170.11 (9)	C2—C6—H6C	109.5
N2—Co1—O3ⁱⁱ	91.63 (8)	H6A—C6—H6B	109.5
N2—Co1—O4ⁱ	104.59 (8)	H6A—C6—H6C	109.5
N2—Co1—N1	87.07 (9)	H6B—C6—H6C	109.5
O1—S1—Co1ⁱⁱⁱ	116.43 (7)	N2—C7—H7	118.2
O1—S1—O3	108.92 (10)	N2—C7—C8	123.6 (3)
O1—S1—O4	109.93 (11)	C8—C7—H7	118.2
O2—S1—Co1ⁱⁱⁱ	133.48 (9)	C7—C8—C12	120.8 (3)
O2—S1—O1	110.07 (11)	C9—C8—C7	116.8 (3)
O2—S1—O3	112.71 (12)	C9—C8—C12	122.4 (3)
O2—S1—O4	112.15 (12)	C8—C9—H9	119.7
O3—S1—Co1ⁱⁱⁱ	53.22 (7)	C10—C9—C8	120.6 (3)
O4—S1—Co1ⁱⁱⁱ	50.06 (7)	C10—C9—H9	119.7
O4—S1—O3	102.82 (11)	C9—C10—H10	120.6
S1—O1—Co1	121.04 (10)	C9—C10—C11	118.7 (3)
Co1ⁱⁱ—O3—Co1ⁱⁱⁱ	124.11 (9)	C11—C10—H10	120.6
S1—O3—Co1ⁱⁱ	141.48 (12)	N2—C11—C10	122.3 (3)
S1—O3—Co1ⁱⁱⁱ	93.57 (9)	N2—C11—H11	118.9
S1—O4—Co1ⁱⁱⁱ	97.36 (9)	C10—C11—H11	118.9
C1—N1—Co1	124.8 (2)	C8—C12—H12A	109.5
C1—N1—C5	117.5 (3)	C8—C12—H12B	109.5
C5—N1—Co1	117.4 (2)	C8—C12—H12C	109.5
C7—N2—Co1	121.9 (2)	H12A—C12—H12B	109.5
C7—N2—C11	118.1 (3)	H12A—C12—H12C	109.5
C11—N2—Co1	120.0 (2)	H12B—C12—H12C	109.5

Co1ⁱⁱⁱ—S1—O1—Co1	−1.75 (15)	O4—S1—O3—Co1ⁱⁱⁱ	−7.25 (10)
Co1ⁱⁱⁱ—S1—O3—Co1ⁱⁱ	−168.6 (2)	N1—C1—C2—C3	−0.5 (5)
Co1—N1—C1—C2	173.9 (3)	N1—C1—C2—C6	179.7 (4)
Co1—N1—C5—C4	−174.0 (3)	N2—C7—C8—C9	1.5 (5)
Co1—N2—C7—C8	−179.4 (2)	N2—C7—C8—C12	179.5 (3)
Co1—N2—C11—C10	178.4 (2)	C1—N1—C5—C4	0.4 (5)
O1—S1—O3—Co1ⁱⁱⁱ	109.34 (9)	C1—C2—C3—C4	0.8 (5)
O1—S1—O3—Co1ⁱⁱ	−59.3 (2)	C2—C3—C4—C5	−0.6 (6)
O1—S1—O4—Co1ⁱⁱⁱ	−108.29 (10)	C3—C4—C5—N1	−0.1 (6)
O2—S1—O1—Co1	176.64 (13)	C5—N1—C1—C2	−0.1 (5)
O2—S1—O3—Co1ⁱⁱⁱ	−128.20 (11)	C6—C2—C3—C4	−179.4 (4)
O2—S1—O3—Co1ⁱⁱ	63.1 (2)	C7—N2—C11—C10	−0.6 (4)
O2—S1—O4—Co1ⁱⁱⁱ	128.92 (11)	C7—C8—C9—C10	−1.5 (5)
O3—S1—O1—Co1	−59.31 (15)	C8—C9—C10—C11	0.6 (5)
O3—S1—O4—Co1ⁱⁱⁱ	7.57 (11)	C9—C10—C11—N2	0.5 (5)
O4—S1—O1—Co1	52.63 (15)	C11—N2—C7—C8	−0.5 (4)
O4—S1—O3—Co1ⁱⁱ	−175.90 (17)	C12—C8—C9—C10	−179.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.93	2.53	3.116 (4)	121
C3—H3···O2^iv	0.93	2.46	3.135 (4)	129
C5—H5···O1	0.93	2.49	3.070 (4)	121

Symmetry codes: (i) y, −x+1, −z+1; (iv) x+1/2, −y+3/2, −z+1/2.

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. CHE-1429086).

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