Bis(4-amino­phenyl­hydroxamato-κ2O,O′)copper(II) methanol disolvate

Zhao, Y.; Chen, Y.

doi:10.1107/S2414314618000330

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180033

https://doi.org/10.1107/S2414314618000330

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Bis(4-aminophenylhydroxamato-κ²O,O′)copper(II) methanol disolvate

Yansi Zhao ^a and Yanmei Chen ^a ^*

^aHubei Key Laboratory for Processing and Application of Catalytic Materials, College of Chemistry and Chemical Engineering, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: cingym@163.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 17 October 2017; accepted 6 January 2018; online 12 January 2018)

In the title complex, [Cu(C₇H₇N₂O₂)₂]·2CH₃OH, the metal centre is coordinated by two 4-aminophenylhydroxamate bidentate ligands, in a distorted square-planar geometry. The asymmetric unit is completed by two methanol solvent molecules, which are involved in hydrogen bonding with N—H functionalities of the free hydroxamate groups. The crystal structure also features N—H⋯O bonds formed by the NH₂ groups, and O—H⋯O hydrogen bonds with the methanol solvent molecules as donors.

Keywords: crystal structure; copper complex; 4-aminophenylhydroxamic acid; solvate; hydrogen bonds.

CCDC reference: 1555577

Structure description

The asymmetric unit of the title compound consists of a Cu^II metal centre bound to two bidentate 4-Apha⁻ ligands (4-AphaH is 4-aminophenylhydroxamic acid) in a distorted square-planar geometry, to form [Cu(4-Apha)₂]. A weak interaction exists between two neighbouring [Cu(4-Apha)₂] molecules, forming a contact between the metal and the free amino NH₂ group of the ligand 4-Apha⁻ (Fig. 1). The compound crystallizes with two methanol molecules for each [Cu(4-Apha)₂] complex in the crystal. The Cu—O bond lengths range from 1.9208 (13) to 1.9583 (14) Å, which agrees well with the values observed in related structures (e.g. Chen et al., 2015 ; Gaynor et al., 2001 ). The apical Cu⋯N contact is 2.487 (2) Å, which is larger than that reported for five-coordinated Cu^II complexes (e.g. Applegate et al., 2003 ). It may be thus be considered as a weak interaction between the Cu^II ion and the NH₂ group, which was not observed in the hydrate of the same complex (Gaynor et al., 2001). The Cu⋯Cu distance in the centrosymmetric pseudo-dimers resulting from these contacts is 8.8174 (8) Å.

Figure 1
The structure of title complex, with displacement ellipsoids drawn at the 30% probability level. Two complexes are represented, in order to emphasize contacts involving the NH₂ group in the ligand (dashed bonds). [Symmetry code: (A) −x, 1 − y, 1 − z.]

In the crystal, N—H⋯O hydrogen bonds are formed between the NH₂ groups of 4-Apha⁻ as hydrogen-bond donors and O atoms of the O—N(H)– hydroxamate groups as hydrogen-bond acceptors. The methanol solvent molecules are connected to the [Cu(4-Apha)₂] complex molecules through N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional supramolecular network structure (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.86	2.05	2.848 (2)	154
N3—H3⋯O6ⁱ	0.86	2.03	2.840 (2)	157
N2—H2B⋯O2ⁱⁱ	0.85 (3)	2.30 (3)	3.147 (3)	175 (2)
N4—H4A⋯O4ⁱⁱⁱ	0.81 (3)	2.34 (3)	3.149 (3)	171 (3)
O5—H5A⋯O2^iv	0.82	1.93	2.745 (2)	179
O6—H6A⋯O4^v	0.82	1.94	2.756 (2)	173
Symmetry codes: (i) x-1, y-1, z+1; (ii) x, y+1, z; (iii) x, y-1, z; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z+1.

Figure 2
Crystal packing of title complex, viewed down the a axis, with hydrogen bonds drawn as dashed lines.

Synthesis and crystallization

A mixture of 4-AphaH (0.0306 g, 0.2 mmol), Cu(CH₃COO)₂·H₂O (0.0199 g, 0.1 mmol) and methanol (1 ml) was sealed in a 6 ml Pyrex tube. The tube was heated to 323 K for a day under autogenous pressure. Slow cooling of the resultant solution to room temperature gave green rod-shaped crystals [yield 0.0230 g (56% based on Cu)].

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Cu(C₇H₇N₂O₂)₂]·2CH₄O
M_r	429.92
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	288
a, b, c (Å)	7.3969 (7), 9.7196 (10), 13.6589 (14)
α, β, γ (°)	75.309 (1), 82.904 (1), 83.066 (1)
V (Å³)	938.53 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.20
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005 )
T_min, T_max	0.714, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	6568, 3301, 2962
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.071, 1.03
No. of reflections	3301
No. of parameters	264
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29
Computer programs: APEX2 and SAINT (Bruker, 2005), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and DIAMOND (Brandenburg, 1999 ).

Structural data

CCDC reference: 1555577

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000330/bh4030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000330/bh4030Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(4-aminobenzhydroxamato-κ²O,O')copper(II) methanol disolvate top

Crystal data top

[Cu(C₇H₇N₂O₂)₂]·2CH₄O	Z = 2
M_r = 429.92	F(000) = 446
Triclinic, P1	D_x = 1.521 Mg m⁻³
a = 7.3969 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7196 (10) Å	Cell parameters from 3706 reflections
c = 13.6589 (14) Å	θ = 2.8–27.3°
α = 75.309 (1)°	µ = 1.20 mm⁻¹
β = 82.904 (1)°	T = 288 K
γ = 83.066 (1)°	Rod, green
V = 938.53 (16) Å³	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	2962 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.016
Absorption correction: multi-scan (SADABS; Bruker, 2005)	θ_max = 25.0°, θ_min = 2.4°
T_min = 0.714, T_max = 0.795	h = −8→8
6568 measured reflections	k = −11→11
3301 independent reflections	l = −16→16

Refinement top

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)] = 0.027	Hydrogen site location: mixed
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0354P)² + 0.4758P] where P = (F_o² + 2F_c²)/3
3301 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Refinement. Hydrogen atoms of the non-coordinating amine group N4 were found in a difference map and refined with free coordinates and isotropic displacement parameters. Other H atoms were placed geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.96 (methyl), O—H = 0.82 and N—H = 0.86 Å. For these H atoms, isotropic displacement parameters were based on U_eq parameters of their carrier atoms.

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

	x	y	z	U_iso*/U_eq
Cu1	0.03678 (3)	0.05781 (2)	0.68807 (2)	0.02744 (10)
N1	0.2586 (2)	0.17752 (17)	0.52451 (13)	0.0308 (4)
H1	0.3254	0.1947	0.4674	0.037*
C1	0.2397 (3)	0.4293 (2)	0.52501 (14)	0.0243 (4)
O1	0.1102 (2)	0.24819 (14)	0.65777 (10)	0.0308 (3)
O2	0.2065 (2)	0.04134 (14)	0.56879 (11)	0.0315 (3)
C2	0.1814 (3)	0.5281 (2)	0.58312 (15)	0.0322 (5)
H2	0.1354	0.4959	0.6506	0.039*
N2	0.2485 (3)	0.87055 (19)	0.39870 (17)	0.0351 (4)
H2A	0.322 (3)	0.894 (3)	0.355 (2)	0.037 (8)*
H2B	0.233 (3)	0.920 (3)	0.442 (2)	0.044 (7)*
N3	−0.1200 (2)	−0.07629 (17)	0.87137 (13)	0.0317 (4)
H3	−0.1720	−0.0961	0.9325	0.038*
C3	0.1903 (3)	0.6722 (2)	0.54304 (16)	0.0327 (5)
H3A	0.1496	0.7361	0.5833	0.039*
O3	−0.0158 (2)	−0.13922 (14)	0.72716 (10)	0.0326 (3)
O4	−0.0667 (2)	0.05964 (14)	0.82653 (10)	0.0336 (3)
C4	0.2600 (3)	0.7229 (2)	0.44265 (15)	0.0265 (4)
N4	−0.2531 (4)	−0.7465 (2)	0.9708 (2)	0.0553 (6)
H4A	−0.212 (4)	−0.803 (3)	0.937 (2)	0.068 (10)*
H4B	−0.278 (4)	−0.772 (3)	1.024 (2)	0.059 (11)*
C5	0.3258 (3)	0.6242 (2)	0.38504 (16)	0.0328 (5)
H5	0.3774	0.6561	0.3187	0.039*
O5	0.5020 (2)	0.13785 (19)	0.35327 (13)	0.0499 (4)
H5A	0.5889	0.0848	0.3772	0.075*
C6	0.3151 (3)	0.4798 (2)	0.42554 (16)	0.0312 (5)
H6	0.3586	0.4156	0.3860	0.037*
O6	0.7664 (3)	0.9217 (2)	0.07809 (12)	0.0518 (5)
H6A	0.8534	0.9208	0.1102	0.078*
C7	0.2038 (3)	0.2796 (2)	0.57141 (14)	0.0244 (4)
C8	−0.1372 (3)	−0.3207 (2)	0.86329 (15)	0.0258 (4)
C9	−0.1021 (3)	−0.4174 (2)	0.80218 (17)	0.0403 (5)
H9	−0.0533	−0.3859	0.7351	0.048*
C10	−0.1370 (4)	−0.5572 (2)	0.83750 (18)	0.0427 (6)
H10	−0.1086	−0.6197	0.7952	0.051*
C11	−0.2148 (3)	−0.6064 (2)	0.93641 (17)	0.0343 (5)
C12	−0.2552 (3)	−0.5096 (2)	0.99779 (17)	0.0420 (6)
H12	−0.3089	−0.5402	1.0639	0.050*
C13	−0.2166 (3)	−0.3693 (2)	0.96193 (16)	0.0378 (5)
H13	−0.2439	−0.3066	1.0042	0.045*
C14	−0.0894 (3)	−0.1740 (2)	0.81866 (15)	0.0254 (4)
C15	0.5618 (4)	0.2259 (3)	0.25923 (19)	0.0568 (7)
H15A	0.4602	0.2883	0.2313	0.085*
H15B	0.6123	0.1678	0.2134	0.085*
H15C	0.6537	0.2818	0.2687	0.085*
C16	0.6166 (4)	0.8733 (4)	0.1456 (2)	0.0762 (10)
H16A	0.6445	0.7751	0.1798	0.114*
H16B	0.5120	0.8814	0.1085	0.114*
H16C	0.5902	0.9300	0.1947	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03733 (16)	0.01877 (14)	0.02422 (14)	−0.00400 (10)	0.00401 (10)	−0.00424 (10)
N1	0.0383 (10)	0.0180 (8)	0.0316 (9)	−0.0039 (7)	0.0101 (8)	−0.0033 (7)
C1	0.0237 (10)	0.0219 (10)	0.0266 (10)	−0.0018 (8)	−0.0026 (8)	−0.0046 (8)
O1	0.0421 (8)	0.0229 (7)	0.0264 (7)	−0.0064 (6)	0.0054 (6)	−0.0065 (6)
O2	0.0414 (8)	0.0165 (7)	0.0334 (8)	−0.0046 (6)	0.0078 (6)	−0.0047 (6)
C2	0.0443 (13)	0.0260 (10)	0.0240 (10)	−0.0043 (9)	0.0061 (9)	−0.0058 (8)
N2	0.0472 (12)	0.0221 (9)	0.0344 (11)	−0.0087 (8)	0.0006 (10)	−0.0037 (8)
N3	0.0467 (11)	0.0220 (8)	0.0255 (9)	−0.0121 (8)	0.0085 (8)	−0.0056 (7)
C3	0.0428 (12)	0.0244 (10)	0.0320 (11)	−0.0025 (9)	0.0020 (9)	−0.0121 (9)
O3	0.0487 (9)	0.0214 (7)	0.0249 (7)	−0.0038 (6)	0.0081 (6)	−0.0061 (6)
O4	0.0534 (9)	0.0203 (7)	0.0268 (7)	−0.0119 (6)	0.0078 (7)	−0.0064 (6)
C4	0.0269 (10)	0.0218 (10)	0.0305 (11)	−0.0053 (8)	−0.0046 (8)	−0.0038 (8)
N4	0.0826 (18)	0.0269 (11)	0.0549 (16)	−0.0194 (11)	0.0102 (14)	−0.0085 (12)
C5	0.0405 (12)	0.0287 (11)	0.0265 (11)	−0.0062 (9)	0.0054 (9)	−0.0042 (9)
O5	0.0409 (10)	0.0530 (11)	0.0472 (10)	0.0031 (8)	0.0088 (8)	−0.0060 (8)
C6	0.0376 (12)	0.0251 (10)	0.0305 (11)	−0.0028 (9)	0.0050 (9)	−0.0101 (9)
O6	0.0601 (11)	0.0650 (12)	0.0333 (9)	−0.0213 (10)	0.0019 (8)	−0.0134 (8)
C7	0.0245 (10)	0.0219 (10)	0.0258 (10)	−0.0022 (8)	−0.0025 (8)	−0.0043 (8)
C8	0.0304 (11)	0.0207 (10)	0.0256 (10)	−0.0024 (8)	0.0003 (8)	−0.0058 (8)
C9	0.0583 (15)	0.0292 (11)	0.0310 (11)	−0.0080 (10)	0.0111 (10)	−0.0083 (9)
C10	0.0638 (16)	0.0254 (11)	0.0402 (13)	−0.0071 (10)	0.0067 (11)	−0.0147 (10)
C11	0.0383 (12)	0.0236 (10)	0.0403 (12)	−0.0067 (9)	−0.0038 (10)	−0.0049 (9)
C12	0.0600 (16)	0.0318 (12)	0.0312 (12)	−0.0154 (11)	0.0106 (11)	−0.0043 (10)
C13	0.0547 (14)	0.0274 (11)	0.0323 (12)	−0.0099 (10)	0.0074 (10)	−0.0115 (9)
C14	0.0266 (10)	0.0230 (10)	0.0260 (10)	−0.0009 (8)	−0.0008 (8)	−0.0062 (8)
C15	0.0502 (16)	0.0701 (19)	0.0414 (14)	0.0071 (14)	−0.0022 (12)	−0.0045 (13)
C16	0.065 (2)	0.114 (3)	0.0594 (19)	−0.0310 (19)	0.0109 (16)	−0.0355 (19)

Geometric parameters (Å, º) top

Cu1—O1	1.9208 (13)	N4—H4B	0.72 (3)
Cu1—O3	1.9271 (14)	C5—C6	1.379 (3)
Cu1—O4	1.9543 (14)	C5—H5	0.9300
Cu1—O2	1.9583 (14)	O5—C15	1.404 (3)
N1—C7	1.311 (2)	O5—H5A	0.8200
N1—O2	1.387 (2)	C6—H6	0.9300
N1—H1	0.8600	O6—C16	1.397 (3)
C1—C6	1.392 (3)	O6—H6A	0.8200
C1—C2	1.394 (3)	C8—C13	1.390 (3)
C1—C7	1.474 (3)	C8—C9	1.390 (3)
O1—C7	1.277 (2)	C8—C14	1.468 (3)
C2—C3	1.375 (3)	C9—C10	1.366 (3)
C2—H2	0.9300	C9—H9	0.9300
N2—C4	1.405 (3)	C10—C11	1.390 (3)
N2—H2A	0.76 (3)	C10—H10	0.9300
N2—H2B	0.85 (3)	C11—C12	1.395 (3)
N3—C14	1.314 (2)	C12—C13	1.379 (3)
N3—O4	1.390 (2)	C12—H12	0.9300
N3—H3	0.8600	C13—H13	0.9300
C3—C4	1.390 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
O3—C14	1.279 (2)	C15—H15C	0.9600
C4—C5	1.397 (3)	C16—H16A	0.9600
N4—C11	1.375 (3)	C16—H16B	0.9600
N4—H4A	0.81 (3)	C16—H16C	0.9600

O1—Cu1—O3	173.99 (6)	C5—C6—H6	119.6
O1—Cu1—O4	94.34 (6)	C1—C6—H6	119.6
O3—Cu1—O4	84.02 (6)	C16—O6—H6A	109.5
O1—Cu1—O2	83.76 (5)	O1—C7—N1	118.48 (17)
O3—Cu1—O2	96.14 (5)	O1—C7—C1	119.60 (17)
O4—Cu1—O2	163.24 (6)	N1—C7—C1	121.86 (17)
C7—N1—O2	118.74 (16)	C13—C8—C9	117.67 (19)
C7—N1—H1	120.6	C13—C8—C14	124.68 (18)
O2—N1—H1	120.6	C9—C8—C14	117.64 (18)
C6—C1—C2	118.05 (18)	C10—C9—C8	122.1 (2)
C6—C1—C7	124.74 (17)	C10—C9—H9	119.0
C2—C1—C7	117.04 (17)	C8—C9—H9	119.0
C7—O1—Cu1	111.62 (12)	C9—C10—C11	120.3 (2)
N1—O2—Cu1	106.16 (10)	C9—C10—H10	119.8
C3—C2—C1	121.52 (19)	C11—C10—H10	119.8
C3—C2—H2	119.2	N4—C11—C10	120.0 (2)
C1—C2—H2	119.2	N4—C11—C12	121.8 (2)
C4—N2—H2A	114.5 (19)	C10—C11—C12	118.23 (19)
C4—N2—H2B	113.1 (17)	C13—C12—C11	121.0 (2)
H2A—N2—H2B	114 (3)	C13—C12—H12	119.5
C14—N3—O4	118.81 (16)	C11—C12—H12	119.5
C14—N3—H3	120.6	C12—C13—C8	120.7 (2)
O4—N3—H3	120.6	C12—C13—H13	119.7
C2—C3—C4	120.31 (19)	C8—C13—H13	119.7
C2—C3—H3A	119.8	O3—C14—N3	118.59 (17)
C4—C3—H3A	119.8	O3—C14—C8	120.23 (17)
C14—O3—Cu1	111.93 (12)	N3—C14—C8	121.17 (17)
N3—O4—Cu1	106.62 (10)	O5—C15—H15A	109.5
C3—C4—C5	118.57 (18)	O5—C15—H15B	109.5
C3—C4—N2	119.88 (19)	H15A—C15—H15B	109.5
C5—C4—N2	121.31 (19)	O5—C15—H15C	109.5
C11—N4—H4A	119 (2)	H15A—C15—H15C	109.5
C11—N4—H4B	117 (3)	H15B—C15—H15C	109.5
H4A—N4—H4B	119 (3)	O6—C16—H16A	109.5
C6—C5—C4	120.75 (19)	O6—C16—H16B	109.5
C6—C5—H5	119.6	H16A—C16—H16B	109.5
C4—C5—H5	119.6	O6—C16—H16C	109.5
C15—O5—H5A	109.5	H16A—C16—H16C	109.5
C5—C6—C1	120.71 (18)	H16B—C16—H16C	109.5

C7—N1—O2—Cu1	5.9 (2)	C2—C1—C7—N1	−177.68 (19)
C6—C1—C2—C3	2.6 (3)	C13—C8—C9—C10	−2.4 (4)
C7—C1—C2—C3	−172.86 (19)	C14—C8—C9—C10	178.2 (2)
C1—C2—C3—C4	−0.5 (3)	C8—C9—C10—C11	1.9 (4)
C14—N3—O4—Cu1	1.8 (2)	C9—C10—C11—N4	178.6 (2)
C2—C3—C4—C5	−2.1 (3)	C9—C10—C11—C12	−0.2 (4)
C2—C3—C4—N2	172.4 (2)	N4—C11—C12—C13	−179.7 (2)
C3—C4—C5—C6	2.6 (3)	C10—C11—C12—C13	−0.9 (4)
N2—C4—C5—C6	−171.8 (2)	C11—C12—C13—C8	0.3 (4)
C4—C5—C6—C1	−0.5 (3)	C9—C8—C13—C12	1.3 (3)
C2—C1—C6—C5	−2.1 (3)	C14—C8—C13—C12	−179.4 (2)
C7—C1—C6—C5	173.02 (19)	Cu1—O3—C14—N3	0.6 (2)
Cu1—O1—C7—N1	−9.8 (2)	Cu1—O3—C14—C8	−179.01 (14)
Cu1—O1—C7—C1	167.22 (13)	O4—N3—C14—O3	−1.7 (3)
O2—N1—C7—O1	2.5 (3)	O4—N3—C14—C8	177.93 (17)
O2—N1—C7—C1	−174.52 (16)	C13—C8—C14—O3	179.6 (2)
C6—C1—C7—O1	−169.77 (19)	C9—C8—C14—O3	−1.0 (3)
C2—C1—C7—O1	5.4 (3)	C13—C8—C14—N3	0.0 (3)
C6—C1—C7—N1	7.2 (3)	C9—C8—C14—N3	179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	2.05	2.848 (2)	154
N3—H3···O6ⁱ	0.86	2.03	2.840 (2)	157
N2—H2B···O2ⁱⁱ	0.85 (3)	2.30 (3)	3.147 (3)	175 (2)
N4—H4A···O4ⁱⁱⁱ	0.81 (3)	2.34 (3)	3.149 (3)	171 (3)
O5—H5A···O2^iv	0.82	1.93	2.745 (2)	179
O6—H6A···O4^v	0.82	1.94	2.756 (2)	173
O6—H6A···N3^v	0.82	2.70	3.391 (2)	143

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

Funding information

This research was supported by the Natural Science Foundation of Hubei Province (No. 2016CFB147), the Foundation of Hubei Educational Committee (No. D20172904) and Doctoral Fund Project of Huanggang Normal University (grant No. 2015001803).

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