catena-Poly[zinc-μ3-{3,3′-[(1,7-dioxa-4,10-diaza­cyclo­dodecane-4,10-di­yl)bis­(methyl­ene)]dibenzoato}]

Ingram, C.W.; Liao, L.; Bacsa, J.

doi:10.1107/S1600536812043450

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1410

doi:10.1107/S1600536812043450

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catena-Poly[zinc-μ₃-{3,3′-[(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene)]dibenzoato}]

C. W. Ingram,^a ^* L. Liao ^a and J. Bacsa ^b

^aCenter for Functional Nanoscale Materials, Department of Chemistry, Clark Atlanta University, 223 James P. Brawley Drive, Atlanta, GA 30314, USA, and ^bDepartment of Chemistry, Emory University, Atlanta, GA 30322, USA
^*Correspondence e-mail: cingram@cau.edu

(Received 16 September 2012; accepted 18 October 2012; online 27 October 2012)

The Zn^II ion in the title compound, [Zn(C₂₄H₂₈N₂O₆)]_n, is located on a twofold rotation axis and is at the midpoint of a crown-4 moiety of 3,3′-[(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene)]dibenzoate anion. It is octahedrally coordinated by two N atoms and two O atoms of the crown moiety from one ligand and two carboxylate O atoms from two bridging intra-chain ligands. Metallomacrocyclic rings are identified in the structure. The metallomacrocycle contains two Zn^II ions and 14 atoms from the bridging ligands. Repetition of these units gives rise to an infinite zigzag chain along [101]. C—H⋯O hydrogen bonds occur.

Related literature

For coordination polymers including metal-organic framework structures, see: Bai et al. (2012 ); Janiak (2003 ); Kitagawa et al. (2004 ); Li et al. (2012 ); Liao et al. (2012 ); Liu et al. (2012 ); O'Keeffe et al. (2000 ); Suh et al. (2012 ); Yoon et al. (2012 ).

Experimental

Crystal data

[Zn(C₂₄H₂₈N₂O₆)]
M_r = 505.87
Monoclinic, C 2/c
a = 20.7264 (15) Å
b = 8.9791 (7) Å
c = 13.9745 (19) Å
β = 127.200 (4)°
V = 2071.5 (4) Å³
Z = 4
Cu Kα radiation
μ = 2.05 mm⁻¹
T = 173 K
0.48 × 0.14 × 0.11 mm

Data collection

Bruker D8 diffractometer with an APEXII detector
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.414, T_max = 0.685
4413 measured reflections
1684 independent reflections
1538 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.06
1684 reflections
150 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.99	2.57	3.224 (3)	124
C12—H12⋯O2ⁱⁱ	0.95	2.43	3.256 (3)	145
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2009 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043450/mw2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043450/mw2087Isup2.hkl

checkCIF report

Comment top

The title compound 1 is the first of a series of coordination polymers that were synthesized from the ligand LH₂, 3,3'-((1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene)) dibenzoic acid. In these new compounds the metal atoms are positioned in the center of the organic linker.

The asymmetric unit of 1 contains a Zn^II ion and a deprotonated ligand L with formula C₂₄H₂₈N₂O₆Zn. The Zn^II ion is 6-coordinate in a distorted octahedral geometry being bound to two nitrogen atoms and two oxygen atoms of the crown (1,7-diaza-12-crown-4) and two carboxylic oxygen atoms, one from each of two additional intra-chain ligands (Fig. 1). The Zn1—O1, Zn1—O3 and Zn1—N1 bond lengths are 1.978 (2) Å, 2.287 (2) Å and 2.242 (2) Å, respectively. The O1—Zn1—O1 angle is 107.54 (8)°. The shortest distance between two neighboring Zn^II ions in a chain is 9.019 (1) Å.

The Zn^II ion of the Zn(crown-4)²⁺ unit is located on a 2-fold rotation axis. The symmetry independent atoms consist of one half of the ligand with the rotation axis generating the second half of the ligand at the Zn atom. Bond circuits consisting of sixteen-membered metallomacrocycle rings can be identified in the structure. Each ring contains two Zn^II ions and fourteen non-H atoms of the ligand. Each Zn^II ion is a node for three ligands and two connected rings (Fig. 1). The pair of benzene moieties within a metallomacrocycle ring are co-planar within one standard deviation (0.0 (2)°) and the dihedral angle between this plane and the plane of the next two nearest phenyl rings along the 1-D chain is 68.79 (5)°. Repetition of these units creates a 1-D polymer network with an infinite number of these rings.

Related literature top

For coordination polymers including metal-organic framework structures, see: Bai et al. (2012); Janiak (2003); Kitagawa et al. (2004); Li et al. (2012); Liao et al. (2012); Liu et al. (2012); O'Keeffe et al. (2000); Suh et al. (2012); Yoon et al. (2012).

Experimental top

The title compound was synthesized in an autoclave by mixing the ligand, 3,3'-((1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)bis(methylene))dibenzoic acid, LH₂ (2x10^-6 mol), Zn(NO₃)₂.6H₂O (6x10^-6 mol, 1.79 mg), H₂O (0.60 ml) and pyridine (2x10^-3 ml) in a vial of 2 ml capacity. The mixture was heated at 85 °C for 7 d and then cooled to ambient temperature. The white crystals were collected and washed with H₂O by filtration. Elem. anal. calcd. C₂₄H₂₈N₂O₆Zn %: C, 56.98; H, 5.58; N, 5.54; Found: C, 56.99; H, 5.79; N, 5.58.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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 portion of the one-dimensional chain of 1 showing the 16-membered metallomacrocycle rings.

catena-poly[zinc-µ₃-{3,3'-[(1,7-dioxa-4,10-diazacyclododecane-4,10- diyl)bis(methylene)]dibenzoato}] top

Crystal data top

[Zn(C₂₄H₂₈N₂O₆)]	F(000) = 1056
M_r = 505.87	D_x = 1.622 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 20.7264 (15) Å	Cell parameters from 3719 reflections
b = 8.9791 (7) Å	θ = 4.0–67.7°
c = 13.9745 (19) Å	µ = 2.05 mm⁻¹
β = 127.200 (4)°	T = 173 K
V = 2071.5 (4) Å³	Column, colourless
Z = 4	0.48 × 0.14 × 0.11 mm

Data collection top

Bruker D8 diffractometer with an APEXII detector	1684 independent reflections
Radiation source: sealed tube	1538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 512 pixels mm^-1	θ_max = 65.1°, θ_min = 5.4°
ϕ and ω scans with a narrow frame width	h = −24→18
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −10→10
T_min = 0.414, T_max = 0.685	l = −14→15
4413 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0475P)² + 2.6887P] where P = (F_o² + 2F_c²)/3
1684 reflections	(Δ/σ)_max < 0.001
150 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Zn(C₂₄H₂₈N₂O₆)]	V = 2071.5 (4) Å³
M_r = 505.87	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 20.7264 (15) Å	µ = 2.05 mm⁻¹
b = 8.9791 (7) Å	T = 173 K
c = 13.9745 (19) Å	0.48 × 0.14 × 0.11 mm
β = 127.200 (4)°

Data collection top

Bruker D8 diffractometer with an APEXII detector	1684 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1538 reflections with I > 2σ(I)
T_min = 0.414, T_max = 0.685	R_int = 0.029
4413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
1684 reflections	Δρ_min = −0.21 e Å⁻³
150 parameters

Special details top

Experimental. Absorption correction: SADABS (Bruker-AXS, 2008) was used for absorption correction. R(int) was 0.0732 before and 0.0388 after correction. The ratio of minimum to maximum transmission is 0.6049. The λ/2 correction factor is not present.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.00000	0.05167 (4)	0.25000	0.0179 (1)
O1	0.07654 (9)	0.18185 (17)	0.24895 (14)	0.0224 (4)
O2	−0.00673 (9)	0.3592 (2)	0.11945 (15)	0.0325 (5)
O3	0.55621 (9)	0.63747 (19)	0.71322 (13)	0.0254 (4)
N1	0.39893 (11)	0.5343 (2)	0.56752 (16)	0.0193 (5)
C1	0.06066 (13)	0.3070 (3)	0.19486 (19)	0.0213 (6)
C2	0.13504 (13)	0.3887 (2)	0.22567 (19)	0.0196 (6)
C3	0.21035 (13)	0.3696 (2)	0.33678 (19)	0.0201 (6)
C4	0.28068 (13)	0.4328 (2)	0.36223 (19)	0.0200 (6)
C5	0.36142 (13)	0.4041 (2)	0.48377 (19)	0.0206 (6)
C6	0.33847 (13)	0.5969 (3)	0.58104 (19)	0.0232 (6)
C7	0.37416 (14)	0.7072 (3)	0.6834 (2)	0.0258 (7)
C8	0.42804 (14)	0.6450 (3)	0.52237 (19)	0.0247 (6)
C9	0.49985 (14)	0.7382 (3)	0.6195 (2)	0.0255 (7)
C10	0.27460 (13)	0.5139 (3)	0.2717 (2)	0.0229 (6)
C11	0.19960 (14)	0.5358 (3)	0.1619 (2)	0.0235 (7)
C12	0.12995 (13)	0.4758 (2)	0.13890 (19)	0.0204 (6)
H3	0.21390	0.31190	0.39680	0.0240*
H5A	0.35370	0.32330	0.52420	0.0250*
H5B	0.40020	0.36750	0.46990	0.0250*
H6A	0.31330	0.51420	0.59450	0.0280*
H6B	0.29520	0.64700	0.50520	0.0280*
H7A	0.38980	0.80030	0.66420	0.0310*
H7B	0.33420	0.73180	0.69810	0.0310*
H8A	0.38270	0.71270	0.46570	0.0300*
H8B	0.44340	0.59150	0.47690	0.0300*
H9A	0.52510	0.78940	0.58690	0.0310*
H9B	0.48220	0.81430	0.65050	0.0310*
H10	0.32190	0.55410	0.28530	0.0280*
H11	0.19600	0.59300	0.10160	0.0280*
H12	0.07880	0.49400	0.06410	0.0250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0119 (2)	0.0195 (2)	0.0178 (2)	0.0000	0.0066 (2)	0.0000
O1	0.0161 (7)	0.0227 (8)	0.0279 (8)	−0.0020 (6)	0.0131 (7)	0.0024 (6)
O2	0.0159 (8)	0.0391 (10)	0.0287 (9)	−0.0006 (7)	0.0063 (7)	0.0110 (7)
O3	0.0178 (8)	0.0244 (8)	0.0205 (7)	−0.0034 (6)	0.0045 (7)	0.0021 (6)
N1	0.0142 (9)	0.0212 (10)	0.0184 (9)	0.0003 (7)	0.0077 (8)	0.0012 (7)
C1	0.0181 (11)	0.0250 (12)	0.0170 (10)	−0.0017 (9)	0.0086 (9)	−0.0012 (9)
C2	0.0181 (11)	0.0191 (11)	0.0197 (10)	0.0019 (8)	0.0104 (9)	−0.0012 (8)
C3	0.0198 (11)	0.0198 (11)	0.0183 (10)	0.0003 (9)	0.0103 (9)	0.0006 (8)
C4	0.0174 (11)	0.0195 (11)	0.0197 (10)	0.0005 (8)	0.0094 (9)	−0.0016 (8)
C5	0.0154 (10)	0.0218 (11)	0.0192 (10)	0.0000 (8)	0.0077 (9)	0.0007 (8)
C6	0.0129 (10)	0.0291 (12)	0.0198 (10)	0.0051 (9)	0.0058 (9)	0.0020 (9)
C7	0.0181 (11)	0.0279 (12)	0.0226 (11)	0.0082 (9)	0.0077 (9)	0.0021 (9)
C8	0.0207 (11)	0.0264 (12)	0.0190 (10)	−0.0014 (9)	0.0078 (10)	0.0043 (9)
C9	0.0217 (11)	0.0237 (12)	0.0234 (11)	−0.0022 (9)	0.0096 (10)	0.0059 (9)
C10	0.0198 (11)	0.0249 (11)	0.0233 (11)	−0.0033 (9)	0.0126 (10)	−0.0020 (9)
C11	0.0244 (12)	0.0239 (12)	0.0208 (11)	−0.0004 (9)	0.0130 (10)	0.0022 (9)
C12	0.0170 (11)	0.0197 (11)	0.0180 (10)	0.0021 (8)	0.0071 (9)	−0.0008 (8)

Geometric parameters (Å, º) top

Zn1—O1	1.978 (2)	C6—C7	1.515 (3)
Zn1—O1ⁱ	1.978 (2)	C8—C9	1.522 (4)
Zn1—O3ⁱⁱ	2.2869 (19)	C10—C11	1.388 (4)
Zn1—N1ⁱⁱ	2.2422 (19)	C11—C12	1.384 (4)
Zn1—O3ⁱⁱⁱ	2.2869 (19)	C3—H3	0.9500
Zn1—N1ⁱⁱⁱ	2.2422 (19)	C5—H5A	0.9900
O1—C1	1.281 (3)	C5—H5B	0.9900
O2—C1	1.225 (3)	C6—H6A	0.9900
O3—C9	1.431 (3)	C6—H6B	0.9900
O3—C7^iv	1.429 (3)	C7—H7A	0.9900
N1—C5	1.497 (3)	C7—H7B	0.9900
N1—C6	1.486 (4)	C8—H8A	0.9900
N1—C8	1.487 (4)	C8—H8B	0.9900
C1—C2	1.516 (4)	C9—H9A	0.9900
C2—C3	1.395 (3)	C9—H9B	0.9900
C2—C12	1.392 (3)	C10—H10	0.9500
C3—C4	1.395 (4)	C11—H11	0.9500
C4—C5	1.521 (3)	C12—H12	0.9500
C4—C10	1.398 (3)

O1—Zn1—O1ⁱ	107.54 (8)	N1—C8—C9	114.72 (19)
O1—Zn1—O3ⁱⁱ	163.85 (7)	O3—C9—C8	106.6 (2)
O1—Zn1—N1ⁱⁱ	90.57 (8)	C4—C10—C11	120.2 (3)
O1—Zn1—O3ⁱⁱⁱ	85.26 (7)	C10—C11—C12	121.0 (2)
O1—Zn1—N1ⁱⁱⁱ	113.40 (8)	C2—C12—C11	119.8 (2)
O1ⁱ—Zn1—O3ⁱⁱ	85.26 (7)	C2—C3—H3	119.00
O1ⁱ—Zn1—N1ⁱⁱ	113.40 (8)	C4—C3—H3	119.00
O1ⁱ—Zn1—O3ⁱⁱⁱ	163.85 (7)	N1—C5—H5A	108.00
O1ⁱ—Zn1—N1ⁱⁱⁱ	90.57 (8)	N1—C5—H5B	108.00
O3ⁱⁱ—Zn1—N1ⁱⁱ	75.01 (7)	C4—C5—H5A	108.00
O3ⁱⁱ—Zn1—O3ⁱⁱⁱ	84.09 (7)	C4—C5—H5B	108.00
O3ⁱⁱ—Zn1—N1ⁱⁱⁱ	75.37 (7)	H5A—C5—H5B	107.00
O3ⁱⁱⁱ—Zn1—N1ⁱⁱ	75.37 (7)	N1—C6—H6A	109.00
N1ⁱⁱ—Zn1—N1ⁱⁱⁱ	139.73 (7)	N1—C6—H6B	109.00
O3ⁱⁱⁱ—Zn1—N1ⁱⁱⁱ	75.01 (7)	C7—C6—H6A	109.00
Zn1—O1—C1	126.99 (19)	C7—C6—H6B	109.00
C7^iv—O3—C9	114.52 (19)	H6A—C6—H6B	108.00
Zn1ⁱⁱ—O3—C9	115.48 (17)	C6—C7—H7A	110.00
Zn1ⁱⁱ—O3—C7^iv	116.02 (14)	C6—C7—H7B	110.00
C5—N1—C6	108.4 (2)	H7A—C7—H7B	109.00
C5—N1—C8	110.03 (19)	O3^iv—C7—H7A	110.00
Zn1ⁱⁱ—N1—C5	107.87 (12)	O3^iv—C7—H7B	110.00
C6—N1—C8	113.0 (2)	N1—C8—H8A	109.00
Zn1ⁱⁱ—N1—C6	105.39 (13)	N1—C8—H8B	109.00
Zn1ⁱⁱ—N1—C8	111.90 (16)	C9—C8—H8A	109.00
O1—C1—O2	126.6 (3)	C9—C8—H8B	109.00
O1—C1—C2	113.7 (2)	H8A—C8—H8B	108.00
O2—C1—C2	119.6 (2)	O3—C9—H9A	110.00
C1—C2—C3	121.2 (2)	O3—C9—H9B	110.00
C1—C2—C12	119.7 (2)	C8—C9—H9A	110.00
C3—C2—C12	118.9 (3)	C8—C9—H9B	110.00
C2—C3—C4	121.8 (2)	H9A—C9—H9B	109.00
C3—C4—C5	119.4 (2)	C4—C10—H10	120.00
C3—C4—C10	118.2 (2)	C11—C10—H10	120.00
C5—C4—C10	122.4 (3)	C10—C11—H11	119.00
N1—C5—C4	116.19 (17)	C12—C11—H11	120.00
N1—C6—C7	113.6 (2)	C2—C12—H12	120.00
O3^iv—C7—C6	106.6 (2)	C11—C12—H12	120.00

O1ⁱ—Zn1—O1—C1	−36.0 (2)	O1—C1—C2—C3	−28.4 (3)
N1ⁱⁱ—Zn1—O1—C1	−150.78 (19)	O1—C1—C2—C12	146.7 (2)
O3ⁱⁱⁱ—Zn1—O1—C1	133.96 (19)	O2—C1—C2—C3	155.2 (2)
N1ⁱⁱⁱ—Zn1—O1—C1	62.5 (2)	O2—C1—C2—C12	−29.7 (4)
Zn1—O1—C1—O2	−11.7 (4)	C1—C2—C3—C4	173.8 (2)
Zn1—O1—C1—C2	172.18 (15)	C12—C2—C3—C4	−1.3 (3)
C7^iv—O3—C9—C8	−176.1 (2)	C1—C2—C12—C11	−172.2 (2)
Zn1ⁱⁱ—O3—C9—C8	−37.4 (3)	C3—C2—C12—C11	3.0 (3)
C9—O3—C7^iv—C6^iv	160.4 (2)	C2—C3—C4—C5	−178.2 (2)
C6—N1—C5—C4	53.7 (3)	C2—C3—C4—C10	−1.7 (3)
C8—N1—C5—C4	−70.4 (3)	C3—C4—C5—N1	−110.1 (2)
Zn1ⁱⁱ—N1—C5—C4	167.3 (2)	C10—C4—C5—N1	73.5 (3)
C5—N1—C6—C7	167.45 (19)	C3—C4—C10—C11	3.0 (4)
C8—N1—C6—C7	−70.3 (2)	C5—C4—C10—C11	179.4 (2)
Zn1ⁱⁱ—N1—C6—C7	52.2 (2)	N1—C6—C7—O3^iv	−49.9 (3)
C5—N1—C8—C9	−151.4 (2)	N1—C8—C9—O3	45.1 (3)
C6—N1—C8—C9	87.3 (3)	C4—C10—C11—C12	−1.3 (4)
Zn1ⁱⁱ—N1—C8—C9	−31.5 (3)	C10—C11—C12—C2	−1.7 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱⁱ	0.99	2.57	3.224 (3)	124
C12—H12···O2^v	0.95	2.43	3.256 (3)	145

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂₄H₂₈N₂O₆)]
M_r	505.87
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	20.7264 (15), 8.9791 (7), 13.9745 (19)
β (°)	127.200 (4)
V (Å³)	2071.5 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.05
Crystal size (mm)	0.48 × 0.14 × 0.11

Data collection
Diffractometer	Bruker D8 diffractometer with an APEXII detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.414, 0.685
No. of measured, independent and observed [I > 2σ(I)] reflections	4413, 1684, 1538
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.06
No. of reflections	1684
No. of parameters	150
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.21

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.9900	2.5700	3.224 (3)	124
C12—H12···O2ⁱⁱ	0.9500	2.4300	3.256 (3)	145

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

Acknowledgements

Financial support for this work by USA NSF/CREST/CFNM Award No. HRD-1137751 is gratefully acknowledged.

References

Bai, S.-Q., Yong, A. M., Hu, J. J., Young, D. J., Zhang, X., Zong, Y., Xu, J., Zuo, J.-L. & Hor, T. S. A. (2012). CrystEngComm, 14, 961–971. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Janiak, C. (2003). Dalton Trans. pp. 2781–2804. Web of Science CrossRef Google Scholar
Kitagawa, S., Kitaura, R. & Noro, S. (2004). Angew. Chem. Int. Ed. 43, 2334–2375. Web of Science CrossRef CAS Google Scholar
Li, J.-R., Sculley, J. & Zhou, H.-C. (2012). Chem. Rev. 112, 869–932. Web of Science CrossRef CAS PubMed Google Scholar
Liao, L., Ingram, C. W., Vandeveer, D., Hardcastle, K., Solntsev, K. M., Sabo, D., Zhang, Z. J. & Weber, R. T. (2012). Inorg. Chim. Acta, 391, 1–9. Web of Science CSD CrossRef CAS Google Scholar
Liu, Y.-Y., Li, J., Ma, J.-F., Ma, J.-C. & Yang, J. (2012). CrystEngComm, 14, 169–177. Web of Science CSD CrossRef CAS Google Scholar
O'Keeffe, M., Eddaoudi, M., Li, H., Reineke, T. & Yaghi, O. M. (2000). J. Solid State Chem. 152, 3–20. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suh, M. P., Park, H. J., Prasad, T. K. & Lim, D.-W. (2012). Chem. Rev. 112, 782–835. Web of Science CrossRef CAS PubMed Google Scholar
Yoon, M., Srirambalaji, R. & Kim, K. (2012). Chem. Rev. 112, 1196–1231. Web of Science CrossRef CAS PubMed Google Scholar

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