Crystal structure of bis­(1,3-di­amino­propane-κ2N,N′)bis­[2-(4-nitro­phen­yl)acetato-κO]zinc(II)

Roberts, T.J.; Mehari, T.F.; Assefa, Z.; Hamby, T.; Sykora, R.E.

doi:10.1107/S2056989015022380

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages m240-m241

https://doi.org/10.1107/S2056989015022380

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Crystal structure of bis(1,3-diaminopropane-κ²N,N′)bis[2-(4-nitrophenyl)acetato-κO]zinc(II)

T. J. Roberts,^a T. F. Mehari,^a Z. Assefa,^a ^* T. Hamby ^b and R. E. Sykora ^b

^a1601 E Market St., Department of Chemistry, North Carolina, A & T State University, Greensboro, NC 27411, USA, and ^bUniversity of South Alabama, Department of Chemistry, Mobile, AL 36688-0002 USA
^*Correspondence e-mail: zassefa@ncat.edu

Edited by P. C. Healy, Griffith University, Australia (Received 9 October 2015; accepted 23 November 2015; online 6 December 2015)

In the structure of the title compound, [Zn(C₈H₆NO₄)₂(C₃H₁₀N₂)₂], the Zn^II atom is located on a center of symmetry with one independent Zn—O distance of 2.199 (2) Å, and two Zn—N distances of 2.157 (2) and 2.144 (2) Å. The overall coordination geometry around the Zn^II atom is octahedral. Several types of hydrogen-bonding interactions are evident. Both intramolecular [2.959 (3) Å] and intermolecular [3.118 (3) and 3.124 (3) Å interactions occur between the O atoms of the acetate group and the amino N atoms, and weak intermolecular C—H—O interactions involving the nitro groups, leading to an extended chain of the molecules aligned along the ac plane.

Keywords: crystal structure; zinc complex; coordination.

CCDC reference: 1438434

1. Related literature

For related polymeric Zn^II tetrahedral structural studies, see: Sheng et al. (2014 ).

2. Experimental

2.1. Crystal data

[Zn(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]
M_r = 573.91
Monoclinic, P 2₁ /c
a = 14.3933 (18) Å
b = 11.0261 (14) Å
c = 8.2453 (11) Å
β = 105.119 (13)°
V = 1263.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 180 K
0.24 × 0.21 × 0.08 mm

2.2. Data collection

Agilent Xcalibur, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.952, T_max = 1.000
5782 measured reflections
2243 independent reflections
1858 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.075
S = 1.06
2243 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.90	2.14	2.959 (3)	150
N1—H1A⋯O2ⁱ	0.90	2.26	3.118 (3)	158
N2—H2D⋯O2ⁱⁱ	0.90	2.25	3.124 (3)	165
C10—H10A⋯O4ⁱⁱⁱ	0.97	2.70	3.634 (3)	161
C7—H7⋯O3^iv	0.93	2.46	3.209 (3)	138
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z-1; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Olex2.solve (Bourhis et al., 2015 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1438434

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022380/hg5460sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989015022380/hg5460Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022380/hg5460Isup3.hkl

checkCIF report

Chemical context top

The structure shows a weak N—H···O intramolecular H-bonding interaction involving a N atom of the diaminopropane ligand and an O atom of the nitrophenylacetic acid ligand. Additional intermolecular N—H···O H-bonding interactions involving these same ligands are also present. Several weak intermolecular H-bonding interactions of the C—H—O type also exist involving the nitro groups and neigbouring phenyl protons. The asymmetric unit consist of half of the molecule as the Zn atom is located at center of symmetry.

Structural commentary top

The structure shows a weak H-bond intramolecular N—H···O interaction involving the N atoms of the diaminopropane ligand and the O atoms of nitrophenylacetic acid ligand. Several weak intermolecular H-bonding interactions of the C—H—O type also exist involving the nitro groups and neigbouring C—H protons. The asymmetric unit consist of half of the molecule as the Zn atom is located at center of symmetry.

Supramolecular features top

H-atoms were placed in calculated positions and allowed to ride during subsequent refinement, with U_iso(H) = 1.2U_eq(C) and C—H distances of 0.93 Å for aromatic hydrogens, U_iso(H) = 1.2U_eq(C) and C—H distances of 0.97 Å for secondary methyl hydrogens, and U_iso(H) = 1.2U_eq(N) and N—H distances of 0.90 Å for amino hydrogens.

Synthesis and crystallization top

Undergraduate student participants enrolled in an open inquiry laboratory (OIL) course conducted the synthesis and charcterization procedures. 0.2 mmol (27.2 mg) of anhydrous ZnCl₂, 0.4 mmol (29.7 mg) of 1,3-diaminopropane, and 0.4 mmol (72.5 mg) of 4- nitrophenylacetic acid were weighed and added into a 25-mL round-bottom flask containing 10 mL of 1:1 CH₃CN/H₂O mixture. The flask was connected to a condenser and placed on a sand bath and refluxed for 1 hr. The flask was then removed from the sandbath and cooled to room temperature. After filtering the solution, the clear supernatant was collected, and covered with a parafilm for slow evaporation. Single crystals suitable for X-ray measurement were found after several days.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For related polymeric Zn^II tetrahedral structural studies, see: Sheng et al. (2014).

Structure description top

For related polymeric Zn^II tetrahedral structural studies, see: Sheng et al. (2014).

Synthesis and crystallization top

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: Olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A thermal ellipsoid diagram of the title compound.
	Fig. 2. A packing diagram of the title compound.

Bis(1,3-diaminopropane-κ²N,N')bis[2-(4-nitrophenyl)acetato-κO]zinc(II) top

Crystal data top

[Zn(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]	F(000) = 600
M_r = 573.91	D_x = 1.509 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3933 (18) Å	Cell parameters from 2201 reflections
b = 11.0261 (14) Å	θ = 3.2–27.2°
c = 8.2453 (11) Å	µ = 1.03 mm⁻¹
β = 105.119 (13)°	T = 180 K
V = 1263.3 (3) Å³	, colourless
Z = 2	0.24 × 0.21 × 0.08 mm

Data collection top

Agilent Xcalibur, Eos diffractometer	2243 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1858 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 16.0514 pixels mm^-1	θ_max = 25.1°, θ_min = 2.9°
ω scans	h = −16→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −13→12
T_min = 0.952, T_max = 1.000	l = −9→9
5782 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0245P)² + 0.7294P] where P = (F_o² + 2F_c²)/3
2243 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Zn(C₈H₆NO₄)₂(C₃H₁₀N₂)₂]	V = 1263.3 (3) Å³
M_r = 573.91	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3933 (18) Å	µ = 1.03 mm⁻¹
b = 11.0261 (14) Å	T = 180 K
c = 8.2453 (11) Å	0.24 × 0.21 × 0.08 mm
β = 105.119 (13)°

Data collection top

Agilent Xcalibur, Eos diffractometer	2243 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1858 reflections with I > 2σ(I)
T_min = 0.952, T_max = 1.000	R_int = 0.027
5782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
2243 reflections	Δρ_min = −0.34 e Å⁻³
169 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.5000	0.5000	1.0000	0.01900 (13)
N3	1.03741 (14)	0.5615 (2)	1.3353 (2)	0.0256 (5)
O3	1.06699 (12)	0.46346 (16)	1.3979 (2)	0.0292 (4)
O2	0.57083 (13)	0.64366 (17)	0.6651 (2)	0.0351 (5)
C1	0.63039 (17)	0.5747 (2)	0.7576 (3)	0.0205 (6)
C4	0.84282 (17)	0.4574 (2)	0.9699 (3)	0.0240 (6)
H4	0.8148	0.3851	0.9235	0.029*
C3	0.81098 (16)	0.5666 (2)	0.8894 (3)	0.0197 (5)
O1	0.61567 (11)	0.50684 (15)	0.8709 (2)	0.0243 (4)
O4	1.07279 (15)	0.65867 (17)	1.3915 (2)	0.0482 (6)
C6	0.95606 (16)	0.5630 (2)	1.1840 (3)	0.0196 (5)
C8	0.85334 (17)	0.6733 (2)	0.9612 (3)	0.0244 (6)
H8	0.8323	0.7468	0.9094	0.029*
C2	0.73151 (16)	0.5702 (2)	0.7286 (3)	0.0240 (6)
H2A	0.7364	0.4989	0.6624	0.029*
H2B	0.7404	0.6409	0.6642	0.029*
C5	0.91535 (17)	0.4548 (2)	1.1176 (3)	0.0220 (6)
H5	0.9362	0.3817	1.1710	0.026*
C7	0.92621 (18)	0.6726 (2)	1.1082 (3)	0.0258 (6)
H7	0.9545	0.7447	1.1551	0.031*
N2	0.40460 (13)	0.42319 (18)	0.7777 (2)	0.0230 (5)
H2C	0.4313	0.4334	0.6913	0.028*
H2D	0.4002	0.3429	0.7937	0.028*
N1	0.45008 (13)	0.67537 (17)	0.9027 (2)	0.0210 (5)
H1A	0.4698	0.7295	0.9863	0.025*
H1B	0.4800	0.6941	0.8227	0.025*
C11	0.30623 (16)	0.4742 (2)	0.7291 (3)	0.0222 (6)
H11A	0.2767	0.4641	0.8214	0.027*
H11B	0.2679	0.4296	0.6334	0.027*
C9	0.34572 (17)	0.6935 (2)	0.8304 (3)	0.0273 (6)
H9A	0.3340	0.7765	0.7918	0.033*
H9B	0.3122	0.6800	0.9168	0.033*
C10	0.30620 (18)	0.6076 (2)	0.6844 (3)	0.0277 (6)
H10A	0.2406	0.6316	0.6301	0.033*
H10B	0.3437	0.6178	0.6032	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0173 (2)	0.0156 (2)	0.0208 (2)	−0.00001 (18)	−0.00090 (15)	0.00156 (17)
N3	0.0224 (11)	0.0271 (13)	0.0249 (12)	0.0014 (11)	0.0017 (9)	0.0007 (10)
O3	0.0300 (10)	0.0269 (10)	0.0277 (10)	0.0089 (9)	0.0020 (8)	0.0051 (8)
O2	0.0287 (10)	0.0400 (12)	0.0358 (11)	0.0111 (10)	0.0069 (8)	0.0188 (9)
C1	0.0219 (12)	0.0209 (14)	0.0165 (12)	−0.0026 (12)	0.0010 (10)	−0.0045 (11)
C4	0.0234 (13)	0.0198 (14)	0.0287 (14)	−0.0019 (12)	0.0068 (11)	−0.0044 (11)
C3	0.0165 (12)	0.0248 (14)	0.0204 (13)	0.0009 (11)	0.0094 (10)	0.0001 (11)
O1	0.0208 (9)	0.0283 (10)	0.0247 (9)	0.0035 (8)	0.0074 (7)	0.0097 (8)
O4	0.0500 (13)	0.0269 (11)	0.0486 (12)	−0.0097 (11)	−0.0210 (10)	−0.0022 (9)
C6	0.0162 (12)	0.0217 (14)	0.0204 (13)	0.0009 (11)	0.0038 (10)	0.0010 (11)
C8	0.0264 (13)	0.0195 (14)	0.0259 (14)	0.0061 (12)	0.0043 (11)	0.0046 (11)
C2	0.0225 (13)	0.0310 (15)	0.0190 (13)	−0.0002 (12)	0.0061 (10)	0.0012 (11)
C5	0.0223 (13)	0.0174 (13)	0.0263 (14)	0.0013 (11)	0.0064 (11)	0.0027 (11)
C7	0.0283 (14)	0.0186 (13)	0.0285 (14)	−0.0025 (12)	0.0039 (11)	−0.0022 (11)
N2	0.0236 (11)	0.0223 (12)	0.0224 (11)	−0.0005 (10)	0.0047 (9)	−0.0013 (9)
N1	0.0235 (11)	0.0194 (11)	0.0182 (10)	−0.0007 (10)	0.0020 (8)	0.0002 (9)
C11	0.0203 (12)	0.0263 (15)	0.0167 (12)	−0.0049 (11)	−0.0012 (10)	−0.0007 (10)
C9	0.0245 (14)	0.0204 (14)	0.0335 (15)	0.0062 (12)	0.0011 (11)	0.0008 (11)
C10	0.0217 (13)	0.0290 (15)	0.0262 (14)	0.0012 (12)	−0.0047 (11)	0.0050 (11)

Geometric parameters (Å, º) top

Zn1—O1	2.1989 (16)	C8—C7	1.381 (3)
Zn1—O1ⁱ	2.1989 (16)	C2—H2A	0.9700
Zn1—N2	2.1565 (18)	C2—H2B	0.9700
Zn1—N2ⁱ	2.1565 (18)	C5—H5	0.9300
Zn1—N1ⁱ	2.1444 (19)	C7—H7	0.9300
Zn1—N1	2.1444 (19)	N2—H2C	0.9000
N3—O3	1.226 (3)	N2—H2D	0.9000
N3—O4	1.224 (3)	N2—C11	1.478 (3)
N3—C6	1.472 (3)	N1—H1A	0.9000
O2—C1	1.246 (3)	N1—H1B	0.9000
C1—O1	1.257 (3)	N1—C9	1.478 (3)
C1—C2	1.536 (3)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C4—C3	1.394 (3)	C11—C10	1.517 (3)
C4—C5	1.382 (3)	C9—H9A	0.9700
C3—C8	1.384 (3)	C9—H9B	0.9700
C3—C2	1.509 (3)	C9—C10	1.520 (3)
C6—C5	1.378 (3)	C10—H10A	0.9700
C6—C7	1.377 (3)	C10—H10B	0.9700
C8—H8	0.9300

O1ⁱ—Zn1—O1	180.00 (9)	C3—C2—H2B	108.9
N2—Zn1—O1ⁱ	90.20 (7)	H2A—C2—H2B	107.7
N2ⁱ—Zn1—O1	90.20 (7)	C4—C5—H5	120.8
N2—Zn1—O1	89.80 (7)	C6—C5—C4	118.5 (2)
N2ⁱ—Zn1—O1ⁱ	89.80 (7)	C6—C5—H5	120.8
N2ⁱ—Zn1—N2	180.0	C6—C7—C8	118.6 (2)
N1ⁱ—Zn1—O1	89.43 (7)	C6—C7—H7	120.7
N1—Zn1—O1	90.57 (7)	C8—C7—H7	120.7
N1—Zn1—O1ⁱ	89.43 (7)	Zn1—N2—H2C	108.4
N1ⁱ—Zn1—O1ⁱ	90.57 (7)	Zn1—N2—H2D	108.4
N1—Zn1—N2	87.65 (7)	H2C—N2—H2D	107.4
N1ⁱ—Zn1—N2ⁱ	87.65 (7)	C11—N2—Zn1	115.69 (14)
N1ⁱ—Zn1—N2	92.35 (7)	C11—N2—H2C	108.4
N1—Zn1—N2ⁱ	92.35 (7)	C11—N2—H2D	108.4
N1ⁱ—Zn1—N1	180.0	Zn1—N1—H1A	107.7
O3—N3—C6	118.6 (2)	Zn1—N1—H1B	107.7
O4—N3—O3	123.2 (2)	H1A—N1—H1B	107.1
O4—N3—C6	118.2 (2)	C9—N1—Zn1	118.60 (15)
O2—C1—O1	126.5 (2)	C9—N1—H1A	107.7
O2—C1—C2	116.9 (2)	C9—N1—H1B	107.7
O1—C1—C2	116.5 (2)	N2—C11—H11A	109.2
C3—C4—H4	119.4	N2—C11—H11B	109.2
C5—C4—H4	119.4	N2—C11—C10	112.0 (2)
C5—C4—C3	121.1 (2)	H11A—C11—H11B	107.9
C4—C3—C2	121.4 (2)	C10—C11—H11A	109.2
C8—C3—C4	118.5 (2)	C10—C11—H11B	109.2
C8—C3—C2	120.1 (2)	N1—C9—H9A	109.3
C1—O1—Zn1	132.51 (15)	N1—C9—H9B	109.3
C5—C6—N3	119.3 (2)	N1—C9—C10	111.5 (2)
C7—C6—N3	118.6 (2)	H9A—C9—H9B	108.0
C7—C6—C5	122.0 (2)	C10—C9—H9A	109.3
C3—C8—H8	119.3	C10—C9—H9B	109.3
C7—C8—C3	121.3 (2)	C11—C10—C9	115.8 (2)
C7—C8—H8	119.3	C11—C10—H10A	108.3
C1—C2—H2A	108.9	C11—C10—H10B	108.3
C1—C2—H2B	108.9	C9—C10—H10A	108.3
C3—C2—C1	113.32 (19)	C9—C10—H10B	108.3
C3—C2—H2A	108.9	H10A—C10—H10B	107.4

Zn1—N2—C11—C10	63.2 (2)	O4—N3—C6—C7	2.9 (3)
Zn1—N1—C9—C10	−59.0 (2)	C8—C3—C2—C1	−92.6 (3)
N3—C6—C5—C4	−176.2 (2)	C2—C1—O1—Zn1	166.11 (15)
N3—C6—C7—C8	176.5 (2)	C2—C3—C8—C7	−180.0 (2)
O3—N3—C6—C5	0.2 (3)	C5—C4—C3—C8	−0.3 (4)
O3—N3—C6—C7	−176.5 (2)	C5—C4—C3—C2	−179.7 (2)
O2—C1—O1—Zn1	−15.1 (4)	C5—C6—C7—C8	−0.1 (4)
O2—C1—C2—C3	138.9 (2)	C7—C6—C5—C4	0.4 (4)
C4—C3—C8—C7	0.7 (4)	N2—Zn1—O1—C1	74.1 (2)
C4—C3—C2—C1	86.7 (3)	N2ⁱ—Zn1—O1—C1	−105.9 (2)
C3—C4—C5—C6	−0.2 (4)	N2ⁱ—Zn1—N1—C9	−135.43 (17)
C3—C8—C7—C6	−0.4 (4)	N2—Zn1—N1—C9	44.58 (17)
O1ⁱ—Zn1—N2—C11	43.83 (16)	N2—C11—C10—C9	−70.8 (3)
O1—Zn1—N2—C11	−136.17 (16)	N1ⁱ—Zn1—O1—C1	166.4 (2)
O1ⁱ—Zn1—N1—C9	−45.65 (17)	N1—Zn1—O1—C1	−13.6 (2)
O1—Zn1—N1—C9	134.35 (17)	N1ⁱ—Zn1—N2—C11	134.41 (16)
O1—C1—C2—C3	−42.2 (3)	N1—Zn1—N2—C11	−45.59 (16)
O4—N3—C6—C5	179.6 (2)	N1—C9—C10—C11	67.2 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.90	2.14	2.959 (3)	150
N1—H1A···O2ⁱⁱ	0.90	2.26	3.118 (3)	158
N2—H2D···O2ⁱⁱⁱ	0.90	2.25	3.124 (3)	165
C10—H10A···O4^iv	0.97	2.70	3.634 (3)	161
C7—H7···O3^v	0.93	2.46	3.209 (3)	138

Symmetry codes: (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1, y, z−1; (v) −x+2, y+1/2, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.90	2.14	2.959 (3)	150.3
N1—H1A···O2ⁱ	0.90	2.26	3.118 (3)	158.3
N2—H2D···O2ⁱⁱ	0.90	2.25	3.124 (3)	165.4
C10—H10A···O4ⁱⁱⁱ	0.97	2.70	3.634 (3)	160.5
C7—H7···O3^iv	0.93	2.46	3.209 (3)	138.1

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z−1; (iv) −x+2, y+1/2, −z+5/2.

Acknowledgements

The Innovation Venture grant provided by the College of Arts and Sciences for curriculum development at NCAT is kindly acknowledged (ZA). The authors also acknowledge support from the National Science Foundation, CHE-0959406 (ZA) and CHE-0846680 (RES).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheng, G. H., Cheng, X. S., You, Z. L. & Zhu, H. L. (2014). Bull. Chem. Soc. Eth. 28, 315–319. Web of Science CrossRef CAS Google Scholar

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Volume 71| Part 12| December 2015| Pages m240-m241

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