Crystal structure of catena-poly[[bis­(N-acethyl­thio­morpholine-κS)copper(I)]-μ-iodido]

Chiang, H.; Kim, T.H.; Park, H.; Kim, J.

doi:10.1107/S2056989016019794

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Volume 73| Part 1| January 2017| Pages 53-55

https://doi.org/10.1107/S2056989016019794

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Crystal structure of catena-poly[[bis(N-acethylthiomorpholine-κS)copper(I)]-μ-iodido]

Hojae Chiang,^a Tae Ho Kim,^a ^* Hyunjin Park ^a and Jineun Kim ^a ^*

^aDepartment of Chemistry (BK21 plus) and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea
^*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by M. Weil, Vienna University of Technology, Austria (Received 1 December 2016; accepted 12 December 2016; online 1 January 2017)

The reaction of copper(I) iodide with N-acetylthiomorpholine (L, C₆H₁₁NOS) in acetonitrile results in a coordination polymer with composition [CuI(L)₂]_n. The Cu^I atom is coordinated by two S atoms and two I atoms, adopting a distorted tetrahedral environment. The μ₂-bridging mode of the I atoms gives rise to chains extending parallel to [010]. C—H⋯O hydrogen-bonding interactions between the chains lead to a three-dimensional network.

Keywords: crystal structure; N-acetylthiomorpholine; coordination polymer; copper(I) iodide.

CCDC reference: 1522053

1. Chemical context

Synthesis, structures and luminescence properties of copper(I) complexes involving CuI and thioethers as co-ligands have been studied extensively (Harvey & Knorr, 2010 ; Knorr et al., 2010 ; Henline et al., 2014 ). The tendency of copper(I) iodide to form aggregates often leads to short Cu—Cu bonds and intriguing diversities in the respective crystal structures (Peng et al., 2010 ), comprising of [CuI]_n chains with split stair motifs (Moreno et al., 1995 ; Blake et al., 1999 ; Cariati et al., 2002 ; Näther et al., 2003 ; Thébault et al., 2006 ), zigzag chains (Munakata et al., 1997 ) or helical chains (Munakata et al., 1997; Kang & Anson, 1995 ). Most of these structures include aromatic nitrogen donor co-ligands. In this context we have studied the interaction of N-acetylthiomorpholine with CuI to investigate the coordination behaviour of the copper(I) atom with the S donor atom of the N-acetylthiomorpholine co-ligand, because both are soft atoms in the sense of the HSAB concept. Although a number of copper(I) complexes with thioether ligands are known (Knorr et al., 2010; Henline et al., 2014), to the best of our knowledge, a [CuI]_n chain structure has not been reported until now. Herein, we report a copper(I) coordination polymer with a zigzag chain [CuI]_n, resulting from the reaction of CuI with N-acetylthiomorpholine (L).

2. Structural commentary

The asymmetric unit of the title compound, [CuI(L)₂]_n, comprises of a copper(I) iodide moiety and two N-acetylthiomorpholine co-ligands (L^A and L^B) and is shown in Fig. 1. The Cu^I atom has a slightly distorted tetrahedral environment (Table 1). The two thiomorpholine rings have the stable chair conformation (Kang et al., 2015 ). The dihedral angles between acetyl CCO and thiomorpholine CNC planes are 3.9 (4) and 6.6 (2)° for L^A and L^B, respectively. The I atoms link neighboring Cu^I atoms in a μ₂-bridging mode into polymeric zigzag chains extending parallel to [010] (Fig. 2).

Table 1
Selected geometric parameters (Å, °)

Cu1—S1	2.3012 (6)	Cu1—I1	2.6221 (3)
Cu1—S2	2.3064 (6)	Cu1—I1ⁱ	2.6476 (3)

S1—Cu1—S2	114.28 (2)	S2—Cu1—I1	101.246 (16)
S1—Cu1—I1	112.179 (17)	I1—Cu1—I1ⁱ	109.949 (9)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The asymmetric unit of the title compound, shown with displacement ellipsoids drawn at the 50% probability level. H atom are shown as small spheres of arbitrary radius.

Figure 2
The polymeric chain structure in [CuI(L)₂] formed through the μ₂-bridging mode of the I atoms. All H atoms have been omitted for clarity.

3. Supramolecular features

As shown in Fig. 3, C10—H10A⋯ O1 hydrogen bonds (yellow dashed lines) between the thiomorpholine ring of L^B and the carbonyl oxygen atoms of L^A result in a layered network parallel to (101). Additional C12—H12B⋯O2 hydrogen bonds between methyl groups of L^B ligands and carbonyl oxygen atoms of neighbouring L^B ligands (red dashed lines) form cyclic centrosymmetric dimers of N-acetylthiomorpholines. The combination of the [CuI]_n chains and the two types of hydrogen-bonding interactions with additional C—H⋯O interactions (Table 2) leads to a three-dimensional network.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2ⁱⁱ	0.99	2.52	3.241 (3)	129
C6—H6B⋯O2ⁱⁱ	0.98	2.47	3.418 (3)	162
C10—H10A⋯O1ⁱⁱⁱ	0.99	2.58	3.144 (3)	116
C12—H12B⋯O2^iv	0.98	2.59	3.372 (3)	137
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z.

Figure 3
The crystal structure of [CuI(L)₂] in a projection along [010]. C—H⋯O hydrogen bonds are shown as yellow and red dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity.

4. Synthesis and crystallization

Preparation of N-acetylthiomorpholine (L)

Thiomorpholine (1.03 g, 0.010 mol) and triethylamine (1.03 g, 0.010 mol) in chloroform (20 mL) were placed in a one-neck round-bottomed flask and kept at 273 K. Then, acetic anhydride (1.02 g, 0.010 mol) was added dropwise. The reactant mixture was stirred for approximately one day. The orange liquid product was purified by using short column chromatography (silica gel, 90% n-hexane and 10% ethyl acetate, R_f = 0.28; yield 1.08 g, 74.5%). ¹H NMR (300 MHz, CDCl₃) / ppm: 3.860 (triplet, 2H, CH₂-N), 3.719 (triplet, 2H, CH₂-N), 2.614 (triplet, 2H, CH₂-S), 2.597 (triplet, 2H, CH₂-S), 2.086 (singlet, 3H, CH₃); ¹³C NMR (300MHz, CDCl₃) / ppm: 168.919 (C=O); 48.993, 43.972 (N—C); 27.248, 27.740 (S—C), 21.527(CH₃)

Preparation of [CuI(L)₂]_n

An acetonitrile (2 mL) solution of L (0.08 g, 0.55 mmol) was allowed to mix with an acetonitrile (3 mL) solution of CuI (0.052 g, 0.27 mmol). The colorless precipitate was filtered and washed with diethyl ether/acetonitrile (3/1 v/v) solution (yield 0.116 g, 88.5%). Single crystals suitable for X-ray analysis were obtained by slow evaporation.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All C-bound H atoms were positioned geometrically, with d(C—H) = 0.99 Å, U_iso = 1.2U_eq(C) for methylene, and d(C—H) = 0.98 Å, U_iso = 1.5U_eq(C) for methyl groups.

Table 3
Experimental details

Crystal data
Chemical formula	[CuI(C₆H₁₁NOS)₂]
M_r	480.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	14.1513 (4), 7.6557 (2), 16.9423 (4)
β (°)	113.805 (1)
V (Å³)	1679.34 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.39
Crystal size (mm)	0.40 × 0.10 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.518, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12664, 3306, 3020
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.045, 1.05
No. of reflections	3306
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1522053

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989016019794/wm5347sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016019794/wm5347Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

catena-poly[[Bis(N-acethylthiomorpholine-κS)copper(I)]-µ-iodido] top

Crystal data top

[CuI(C₆H₁₁NOS)₂]	F(000) = 952
M_r = 480.87	D_x = 1.902 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.1513 (4) Å	Cell parameters from 8258 reflections
b = 7.6557 (2) Å	θ = 2.4–27.4°
c = 16.9423 (4) Å	µ = 3.39 mm⁻¹
β = 113.805 (1)°	T = 173 K
V = 1679.34 (8) Å³	Plate, colourless
Z = 4	0.40 × 0.10 × 0.02 mm

Data collection top

Bruker APEXII CCD diffractometer	3020 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 26.0°, θ_min = 1.6°
T_min = 0.518, T_max = 0.746	h = −13→17
12664 measured reflections	k = −9→9
3306 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.018	H-atom parameters constrained
wR(F²) = 0.045	w = 1/[σ²(F_o²) + (0.0221P)² + 0.5521P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
3306 reflections	Δρ_max = 0.51 e Å⁻³
183 parameters	Δρ_min = −0.37 e Å⁻³

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
Cu1	0.18899 (2)	1.02851 (3)	0.16379 (2)	0.02035 (7)
I1	0.22857 (2)	1.36381 (2)	0.18629 (2)	0.02246 (6)
S1	0.01447 (4)	0.97167 (7)	0.10384 (3)	0.01843 (11)
S2	0.27317 (4)	0.95551 (7)	0.07682 (3)	0.01754 (11)
O1	−0.12671 (13)	0.4134 (2)	0.18413 (10)	0.0306 (4)
O2	0.55531 (13)	0.4901 (2)	0.13221 (10)	0.0326 (4)
N1	−0.12119 (14)	0.6992 (2)	0.15212 (11)	0.0222 (4)
N2	0.41457 (14)	0.6547 (2)	0.05909 (11)	0.0211 (4)
C1	−0.09223 (18)	0.6587 (3)	0.08061 (14)	0.0261 (5)
H1A	−0.1457	0.7049	0.0264	0.031*
H1B	−0.0897	0.5303	0.0747	0.031*
C2	0.01160 (17)	0.7356 (3)	0.09339 (15)	0.0237 (5)
H2A	0.0279	0.7034	0.0437	0.028*
H2B	0.0656	0.6845	0.1459	0.028*
C3	−0.03090 (17)	0.9830 (3)	0.18944 (13)	0.0204 (5)
H3A	0.0220	0.9323	0.2427	0.024*
H3B	−0.0408	1.1068	0.2011	0.024*
C4	−0.13193 (17)	0.8852 (3)	0.16610 (14)	0.0226 (5)
H4A	−0.1559	0.8994	0.2131	0.027*
H4B	−0.1849	0.9365	0.1130	0.027*
C5	−0.13845 (16)	0.5668 (3)	0.19871 (13)	0.0227 (5)
C6	−0.1756 (2)	0.6151 (3)	0.26767 (15)	0.0301 (5)
H6A	−0.2461	0.6610	0.2406	0.045*
H6B	−0.1300	0.7045	0.3054	0.045*
H6C	−0.1748	0.5114	0.3018	0.045*
C7	0.46423 (17)	0.8128 (3)	0.10528 (14)	0.0241 (5)
H7A	0.4710	0.8983	0.0640	0.029*
H7B	0.5345	0.7841	0.1480	0.029*
C8	0.40226 (17)	0.8939 (3)	0.15130 (14)	0.0244 (5)
H8A	0.4389	0.9987	0.1833	0.029*
H8B	0.3973	0.8093	0.1937	0.029*
C9	0.23472 (16)	0.7451 (3)	0.02483 (13)	0.0195 (4)
H9A	0.2295	0.6596	0.0668	0.023*
H9B	0.1658	0.7552	−0.0233	0.023*
C10	0.31244 (17)	0.6798 (3)	−0.00969 (14)	0.0229 (5)
H10A	0.2879	0.5677	−0.0403	0.027*
H10B	0.3172	0.7653	−0.0518	0.027*
C11	0.46543 (18)	0.4999 (3)	0.07934 (14)	0.0234 (5)
C12	0.4073 (2)	0.3374 (3)	0.03610 (18)	0.0339 (6)
H12A	0.4529	0.2358	0.0560	0.051*
H12B	0.3837	0.3489	−0.0266	0.051*
H12C	0.3475	0.3221	0.0508	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02182 (15)	0.01848 (14)	0.02120 (14)	−0.00092 (11)	0.00916 (12)	−0.00102 (10)
I1	0.03471 (10)	0.01382 (8)	0.01707 (8)	−0.00131 (6)	0.00859 (7)	−0.00134 (5)
S1	0.0196 (3)	0.0185 (3)	0.0176 (2)	0.0000 (2)	0.0080 (2)	0.00071 (19)
S2	0.0196 (3)	0.0148 (2)	0.0179 (2)	−0.0001 (2)	0.0073 (2)	−0.00149 (19)
O1	0.0306 (9)	0.0224 (9)	0.0302 (9)	−0.0033 (7)	0.0034 (7)	0.0003 (7)
O2	0.0305 (10)	0.0403 (10)	0.0256 (9)	0.0143 (8)	0.0099 (8)	0.0080 (7)
N1	0.0240 (10)	0.0211 (10)	0.0236 (9)	−0.0025 (8)	0.0119 (8)	−0.0020 (7)
N2	0.0179 (9)	0.0209 (10)	0.0220 (9)	0.0008 (7)	0.0055 (8)	−0.0049 (7)
C1	0.0296 (13)	0.0257 (12)	0.0245 (12)	−0.0081 (10)	0.0123 (10)	−0.0085 (9)
C2	0.0280 (12)	0.0194 (11)	0.0266 (11)	0.0000 (10)	0.0141 (10)	−0.0055 (9)
C3	0.0245 (12)	0.0203 (11)	0.0184 (10)	0.0004 (9)	0.0108 (9)	−0.0017 (8)
C4	0.0224 (12)	0.0221 (12)	0.0257 (11)	0.0038 (9)	0.0122 (10)	0.0023 (9)
C5	0.0128 (11)	0.0265 (12)	0.0199 (11)	−0.0047 (9)	−0.0025 (9)	0.0005 (9)
C6	0.0292 (13)	0.0332 (14)	0.0290 (12)	−0.0054 (11)	0.0129 (11)	0.0064 (10)
C7	0.0185 (11)	0.0270 (12)	0.0246 (11)	−0.0017 (10)	0.0065 (9)	−0.0059 (9)
C8	0.0189 (12)	0.0299 (12)	0.0203 (11)	0.0004 (10)	0.0036 (9)	−0.0079 (9)
C9	0.0179 (11)	0.0171 (10)	0.0197 (10)	−0.0012 (9)	0.0036 (9)	−0.0021 (8)
C10	0.0206 (11)	0.0246 (11)	0.0197 (11)	0.0009 (9)	0.0042 (9)	−0.0065 (9)
C11	0.0311 (13)	0.0254 (12)	0.0234 (11)	0.0058 (10)	0.0211 (11)	0.0055 (9)
C12	0.0403 (15)	0.0210 (12)	0.0523 (16)	0.0006 (11)	0.0308 (13)	0.0014 (11)

Geometric parameters (Å, º) top

Cu1—S1	2.3012 (6)	C3—H3A	0.9900
Cu1—S2	2.3064 (6)	C3—H3B	0.9900
Cu1—I1	2.6221 (3)	C4—H4A	0.9900
Cu1—I1ⁱ	2.6476 (3)	C4—H4B	0.9900
I1—Cu1ⁱⁱ	2.6476 (3)	C5—C6	1.508 (3)
S1—C3	1.810 (2)	C6—H6A	0.9800
S1—C2	1.815 (2)	C6—H6B	0.9800
S2—C9	1.811 (2)	C6—H6C	0.9800
S2—C8	1.814 (2)	C7—C8	1.521 (3)
O1—C5	1.225 (3)	C7—H7A	0.9900
O2—C11	1.227 (3)	C7—H7B	0.9900
N1—C5	1.366 (3)	C8—H8A	0.9900
N1—C1	1.460 (3)	C8—H8B	0.9900
N1—C4	1.462 (3)	C9—C10	1.523 (3)
N2—C11	1.357 (3)	C9—H9A	0.9900
N2—C10	1.457 (3)	C9—H9B	0.9900
N2—C7	1.459 (3)	C10—H10A	0.9900
C1—C2	1.515 (3)	C10—H10B	0.9900
C1—H1A	0.9900	C11—C12	1.508 (3)
C1—H1B	0.9900	C12—H12A	0.9800
C2—H2A	0.9900	C12—H12B	0.9800
C2—H2B	0.9900	C12—H12C	0.9800
C3—C4	1.518 (3)

S1—Cu1—S2	114.28 (2)	O1—C5—N1	121.6 (2)
S1—Cu1—I1	112.179 (17)	O1—C5—C6	120.6 (2)
S2—Cu1—I1	101.246 (16)	N1—C5—C6	117.7 (2)
S1—Cu1—I1ⁱ	108.190 (16)	C5—C6—H6A	109.5
S2—Cu1—I1ⁱ	110.870 (16)	C5—C6—H6B	109.5
I1—Cu1—I1ⁱ	109.949 (9)	H6A—C6—H6B	109.5
Cu1—I1—Cu1ⁱⁱ	126.245 (8)	C5—C6—H6C	109.5
C3—S1—C2	97.16 (10)	H6A—C6—H6C	109.5
C3—S1—Cu1	107.58 (7)	H6B—C6—H6C	109.5
C2—S1—Cu1	102.08 (7)	N2—C7—C8	111.16 (18)
C9—S2—C8	97.32 (10)	N2—C7—H7A	109.4
C9—S2—Cu1	113.27 (7)	C8—C7—H7A	109.4
C8—S2—Cu1	104.68 (7)	N2—C7—H7B	109.4
C5—N1—C1	119.82 (18)	C8—C7—H7B	109.4
C5—N1—C4	125.09 (18)	H7A—C7—H7B	108.0
C1—N1—C4	115.07 (17)	C7—C8—S2	112.12 (15)
C11—N2—C10	124.83 (18)	C7—C8—H8A	109.2
C11—N2—C7	119.84 (18)	S2—C8—H8A	109.2
C10—N2—C7	115.28 (17)	C7—C8—H8B	109.2
N1—C1—C2	112.30 (18)	S2—C8—H8B	109.2
N1—C1—H1A	109.1	H8A—C8—H8B	107.9
C2—C1—H1A	109.1	C10—C9—S2	110.89 (15)
N1—C1—H1B	109.1	C10—C9—H9A	109.5
C2—C1—H1B	109.1	S2—C9—H9A	109.5
H1A—C1—H1B	107.9	C10—C9—H9B	109.5
C1—C2—S1	112.54 (16)	S2—C9—H9B	109.5
C1—C2—H2A	109.1	H9A—C9—H9B	108.0
S1—C2—H2A	109.1	N2—C10—C9	111.90 (17)
C1—C2—H2B	109.1	N2—C10—H10A	109.2
S1—C2—H2B	109.1	C9—C10—H10A	109.2
H2A—C2—H2B	107.8	N2—C10—H10B	109.2
C4—C3—S1	111.67 (14)	C9—C10—H10B	109.2
C4—C3—H3A	109.3	H10A—C10—H10B	107.9
S1—C3—H3A	109.3	O2—C11—N2	121.7 (2)
C4—C3—H3B	109.3	O2—C11—C12	120.4 (2)
S1—C3—H3B	109.3	N2—C11—C12	117.9 (2)
H3A—C3—H3B	107.9	C11—C12—H12A	109.5
N1—C4—C3	111.95 (18)	C11—C12—H12B	109.5
N1—C4—H4A	109.2	H12A—C12—H12B	109.5
C3—C4—H4A	109.2	C11—C12—H12C	109.5
N1—C4—H4B	109.2	H12A—C12—H12C	109.5
C3—C4—H4B	109.2	H12B—C12—H12C	109.5
H4A—C4—H4B	107.9

C5—N1—C1—C2	−120.4 (2)	C11—N2—C7—C8	−120.0 (2)
C4—N1—C1—C2	61.1 (3)	C10—N2—C7—C8	62.5 (2)
N1—C1—C2—S1	−59.4 (2)	N2—C7—C8—S2	−60.5 (2)
C3—S1—C2—C1	52.97 (17)	C9—S2—C8—C7	54.16 (18)
Cu1—S1—C2—C1	162.73 (14)	Cu1—S2—C8—C7	170.60 (15)
C2—S1—C3—C4	−53.85 (17)	C8—S2—C9—C10	−54.05 (16)
Cu1—S1—C3—C4	−158.97 (13)	Cu1—S2—C9—C10	−163.52 (12)
C5—N1—C4—C3	119.1 (2)	C11—N2—C10—C9	118.9 (2)
C1—N1—C4—C3	−62.5 (2)	C7—N2—C10—C9	−63.8 (2)
S1—C3—C4—N1	61.7 (2)	S2—C9—C10—N2	61.7 (2)
C1—N1—C5—O1	2.6 (3)	C10—N2—C11—O2	172.7 (2)
C4—N1—C5—O1	−179.1 (2)	C7—N2—C11—O2	−4.6 (3)
C1—N1—C5—C6	−175.7 (2)	C10—N2—C11—C12	−8.6 (3)
C4—N1—C5—C6	2.6 (3)	C7—N2—C11—C12	174.10 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2ⁱⁱ	0.99	2.52	3.241 (3)	129
C6—H6B···O2ⁱⁱ	0.98	2.47	3.418 (3)	162
C10—H10A···O1ⁱⁱⁱ	0.99	2.58	3.144 (3)	116
C12—H12B···O2^iv	0.98	2.59	3.372 (3)	137

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

Acknowledgements

This research was supported by the Basic Science Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

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