A three-dimensional manganese(II) metal-organic framework based on 5-meth­oxy­benzene-1,3-di­carb­oxy­lic acid and exhibiting a pts net

The solvothermal reaction of MnCl₂·H₂O and 5-meth­oxy­benzene-1,3-di­carb­oxy­lic acid (MeO-m-H₂BDC) led to a three-dimensional Mn^II metal-organic framework, namely poly[(di­methyl­formamide-[kappa]O)([mu]₄-5-meth­oxy­benzene-1,3-di­carb­oxy­lato-[kappa]⁴O¹:O^1':O³,O^3':O³)manganese(II)], [Mn(C₉H₆O₅)(C₃H₇NO)]_n or [Mn(MeO-m-BDC)(DMF)]_n (DMF is di­­methyl­formamide). The Mn^II atom is six-coordinated and exhibits a distorted octahedral geometry formed by five car­boxyl­ate O atoms from four different MeO-m-BDC^2- anionic ligands and by one DMF O atom. The three-dimensional framework of (I) formed by the bridging MeO-m-BDC^2- ligands and the Mn^II atoms exhibits a pts topo­logical network when MeO-m-BDC^2- and Mn^II are viewed as four-connected nodes.

S1. Comment

The design and syntheses of metal–organic frameworks (MOFs) are of great interest, not only due to their tremendous potential applications in nonlinear optics, catalysis, gas absorption, luminescence, magnetism and biomedicine (Evans et al., 2002; Lee et al., 2009; Chen et al., 2010; Wang et al., 2009; Zhang et al., 2007; Horcajada et al., 2012), but also due to their intriguing variety of architectures and topologies (Batten & Robson, 1998; Eddaoudi et al., 2001; Yang et al., 2008). Self-assembly of inorganic metal atoms and organic ligands is one of the most efficient and widely utilized approaches towards the construction of MOFs under hydro(solvo)thermal technique (Hagrman et al., 1999; Hsu et al., 2008). In the last decade, a variety of aromatic polycarboxylates have been widely adopted by the researchers to construct metal–organic frameworks owing to their flexible coordination modes and sensitivity to pH values of the carboxylate groups. For example, Yaghi and co-workers have reported many stable highly porous functionalized open networks based on aromatic polycarboxylates (Britt et al., 2008; Furukawa et al.., 2010). The selection of a ligand is extremely important because changing its geometry can control the structure and topology of the resulting coordination framework. For instance, a simple change in the substitution on the polycarboxylate sometimes can dramatically change the structure and topology of the final MOFs (Huang et al., 2009). It was reported that when benzene-1,3-dicarboxylate (m-H₂BDC) was employed to assemble with Mn^II under the solvothermal conditions, a three-dimensional MOF, Mn₄(m-BDC)₄(µ₂-DMF)₂.2DMF (DMF is dimethylformamide), which exhibits a four-connected sra topological network with a point symbol 4²6³8 constructed by uninodal tetrahedral nodes, can be obtained. This is the Al net of the common structure type of SrAl₂ (Rosi et al., 2005). It crystallizes in the triclinic, P1 space group and is comprised of three crystallographically independent Mn^II atoms and two diverse m-BDC^2- anionic ligands (Luo et al., 2008). In this work, we chose MeO-m-H₂BDC, a derivative of m-H₂BDC, to assemble with Mn^II under solvothermal conditions to investigate the role of the substitutional group in the structural modulation and topology manipulation. Finally, a very different three-dimensional Mn^II MOF, [Mn(MeO-m-BDC)(DMF)]_n, (I), which exhibits a four-connected pts topological network, was isolated. According to a search in the Cambridge Structural Database (Version 5.34; Allen, 2002), only one other MeO-m-BDC^2--based Mn^II coordination polymer has been reported to date, namely [Mn(MeO-m-BDC)(bipy)(H₂O)].H₂O (bipy is 2,2'-bipyridine; Shen, 2009).

Complex (I) crystallizes in the orthorhombic space group Pna2₁ and the asymmetric unit contains one MeO-m-BDC^2- ligand, one Mn^II atom and one coordinated DMF molecule (Fig. 1). It is worth noting that (I) has the same space group and similar cell parameters to [Mn(NH₂-m-BDC)(DMF)]_n (NH₂-m-H₂BDC is 5-aminobenzene-1,3-dicarboxylate; Kongshaug & Fjellvåg, 2007). The compounds are isomorphic after carefully compared their structure. The Mn^II atom in (I) exhibits six-coordination with a distorted octahedral geometry. Four carboxylate O atoms (O4ⁱ, O3ⁱⁱ, O2ⁱⁱⁱ and O1ⁱⁱⁱ; see Table 1 for details and symmetry codes) constitute the equatorial plane, while the remaining carboxylate O atom (O1) and the DMF O atom (O6) occupy the apical positions of the octahedron (Fig. 2). The Mn1—O bond lengths, apart from Mn1—O1ⁱⁱⁱ, vary from 2.112 (2) to 2.210 (2) Å, which are consistent with previously reported results (Perlepes et al., 1991; Yano et al., 1997; Eppley et al., 1995). The Mn1—O1ⁱⁱⁱ bond is a little long [2.583 (2) Å], which can be regarded as a semicoordination mode (Dey et al. 2012). The Mn^II atom and its symmetry-related counterparts are doubly bridged by the carboxylate groups of the MeO-m-BDC^2- ligands to form an infinite chain of MnO₆ polyhedra. The Mn···Mn distance within the chain is 3.8238 (16) Å. Each of the infinite chains is connected to four adjacent chains by the ring system of the MeO-m-BDC^2- ligands, forming the final three-dimensional network. The MeO-m-BDC^2- ligands in this three-dimensional network adopt a µ₄ coordination mode and the network contains one-dimensional channels when viewed along the a axis; the dimensions of these channels are 9.974 × 9.974 Å (measured between atom centers). The DMF ligands and the methoxy groups of the MeO-m-BDC^2- anionic ligands protrude into the channels.

A better insight into the structure of the metal–organic frameworks would be the topological network approach, which has been proved to be an important and essential aspect of the design and analysis of MOF materials (Carlucci et al., 2003; Hill et al., 2005). To understand the structure of (I) more clearly and easily, a topological analysis was conducted using TOPOS4.0. In the present case, each MeO-m-BDC^2- ligand bridges four adjacent Mn^II atoms through its carboxylate O atoms, and each Mn^II atom is also connected to four MeO-m-BDC^2- ligands; thus both the Mn^II atom and MeO-m-BDC^2- ligand can be simplified as four-connected nodes. Therefore, the three-dimensional framework of (I) can be abstracted into a four-connected network with a point symbol 4²8⁴ constructed by distorted square-planar vertices and tetrahedral nodes, as shown in Fig. 3. This is the feature of PtS (cooperite) topology in which the Pt atom forms PtS₄ rectangles and the S atom forms SPt₄ tetrahedra (Blatov et al., 2004; O'Keeffe et al., 2008; Hu et al., 2005). The report of [Mn(NH₂-m-BDC)(DMF)]_n (Kongshaug & Fjellvåg, 2007) only gave a very simple description of the structure and did not analyze its topological structure. By comparison, when m-H₂BDC was substituted by MeO-m-H₂BDC to assemble with Mn^II, the topological structure changed from an sra net to a pts net.

Related literature

For related literature, see: Batten & Robson (1998); Blatov et al. (2004); Britt et al. (2008); Carlucci et al. (2003); Chen et al. (2010); Dey et al. (2012); Eddaoudi et al. (2001); Eppley et al. (1995); Evans & Lin (2002); Furukawa et al. (2010); Hagrman et al. (1999); Hill et al. (2005); Horcajada et al. (2012); Hsu et al. (2008); Hu et al. (2005); Huang et al. (2009); Kongshaug & Fjellvåg (2007); Lee et al. (2009); Luo et al. (2008); O'Keeffe et al. (2008); Perlepes et al. (1991); Rosi et al. (2005); Shen (2009); Wang et al. (2009); Yang et al. (2008); Yano et al. (1997); Zhang et al. (2007).

S2. Experimental

MnCl₂.2H₂O (0.5 mmol) and 5-methoxybenzene-1,3-dicarboxylic acid (1 mmol) were placed in a 20 ml Teflon-lined stainless steel vessel with DMF (8 ml). The mixture was heated to 433 K over a period of 4 h and kept at that temperature for 2 d. The reaction system was cooled slowly to room temperature over a period of 2 d. Pale-yellow prismatic crystals of (I) were collected, washed thoroughly with DMF, and dried in air at room temperature (yield 76%, based on MnCl₂.2H₂O). Elemental analysis (%) calculated for C₁₂H₁₃MnNO₆: C 44.74, H 4.07, N 4.35; found: C 44.68, H 4.15, N 4.24.

S3. Refinement

H atoms attached to the anisotropically refined atoms were placed in geometrically idealized positions and included as riding atoms.

Computing details

Data collection: CrystalClear (Rigaku 2005); cell refinement: CrystalClear (Rigaku 2005); data reduction: CrystalClear (Rigaku 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The coordination environment of the Mn^II atom and the coordination mode of the MeO-m-BDC^2- ligand in (I). The Mn1—O1^iii bond is marked as a dashed line. H atoms have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, z-1/2; (ii) -x+1/2, y+1/2, z-1/2; (iii) x+1/2, -y+3/2, z; (iv) x-1/2, -y+3/2, z; (v) -x+1/2, y-1/2, z+1/2; (vi) -x+1, -y+1, z+1/2.]
	Fig. 3. The three-dimensional equivalent topological network of (I). The light (green in the electronic version of the paper) and dark (pink) nodes represent Mn^II atomss and the MeO-m-BDC^2- anionic ligands, respectively.

Poly[(dimethylformamide-κO)(µ₄-5-methoxyisophthalato-κ⁴O¹:O^1':O³:O^3')manganese(II)]

Crystal data

[Mn(C9H6O5)(C3H7NO)]	F(000) = 660
Mr = 322.17	Dx = 1.682 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3064 reflections
a = 7.437 (3) Å	θ = 3.1–27.5°
b = 15.164 (7) Å	µ = 1.06 mm^−1
c = 11.278 (5) Å	T = 200 K
V = 1271.9 (10) Å^3	Prism, yellow
Z = 4	0.25 × 0.22 × 0.18 mm

Data collection

Rigaku Mercury70 (2x2 bin mode) diffractometer	2851 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SPHERE in CrystalClear; Rigaku, 2005)	h = −9→9
Tmin = 0.777, Tmax = 0.832	k = −19→19
9331 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.047	w = 1/[σ^2(Fo^2) + (0.0217P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2851 reflections	Δρmax = 0.37 e Å^−3
182 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.006 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.46469 (3)	0.779411 (15)	0.71385 (3)	0.01850 (7)
O1	0.26169 (18)	0.73411 (8)	0.83165 (12)	0.0283 (3)
O2	0.07962 (19)	0.62064 (10)	0.83468 (14)	0.0423 (4)
O3	0.20239 (15)	0.37525 (7)	1.12943 (12)	0.0267 (3)
O4	0.49225 (16)	0.35535 (9)	1.17490 (12)	0.0278 (3)
O5	0.73679 (19)	0.66780 (10)	1.12827 (15)	0.0446 (4)
O6	0.64562 (19)	0.80417 (9)	0.56696 (12)	0.0340 (3)
N1	0.7467 (2)	0.88928 (10)	0.41656 (15)	0.0306 (4)
C1	0.2187 (3)	0.65818 (13)	0.86907 (17)	0.0253 (4)
C2	0.3638 (2)	0.39894 (11)	1.13184 (16)	0.0196 (4)
C3	0.3358 (2)	0.61394 (12)	0.96051 (16)	0.0218 (4)
C4	0.2966 (2)	0.52920 (11)	0.99959 (16)	0.0227 (4)
H4	0.1936	0.4993	0.9701	0.027*
C5	0.4083 (2)	0.48800 (11)	1.08206 (15)	0.0201 (4)
C6	0.5604 (2)	0.53224 (13)	1.12449 (17)	0.0246 (4)
H6	0.6394	0.5038	1.1784	0.029*
C7	0.5953 (2)	0.61766 (12)	1.08763 (16)	0.0264 (4)
C8	0.4823 (2)	0.65894 (13)	1.00619 (17)	0.0261 (4)
H8	0.5057	0.7179	0.9820	0.031*
C9	0.8788 (3)	0.62473 (15)	1.1852 (3)	0.0592 (8)
H9A	0.9695	0.6681	1.2092	0.089*
H9B	0.9331	0.5820	1.1308	0.089*
H9C	0.8333	0.5939	1.2554	0.089*
C10	0.6518 (3)	0.87450 (13)	0.51296 (18)	0.0299 (5)
H10	0.5824	0.9220	0.5433	0.036*
C11	0.7441 (3)	0.97403 (15)	0.3578 (2)	0.0423 (6)
H11A	0.6597	1.0133	0.3986	0.064*
H11B	0.7061	0.9663	0.2753	0.064*
H11C	0.8648	0.9999	0.3598	0.064*
C12	0.8643 (4)	0.82111 (17)	0.3690 (2)	0.0559 (7)
H12A	0.8525	0.7674	0.4168	0.084*
H12B	0.9892	0.8416	0.3714	0.084*
H12C	0.8302	0.8084	0.2868	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02000 (11)	0.01417 (12)	0.02134 (11)	0.00103 (10)	0.00070 (15)	−0.00024 (15)
O1	0.0369 (8)	0.0226 (7)	0.0255 (7)	0.0093 (6)	0.0115 (6)	0.0106 (6)
O2	0.0333 (8)	0.0436 (10)	0.0501 (9)	−0.0057 (7)	−0.0147 (7)	0.0228 (8)
O3	0.0202 (6)	0.0224 (7)	0.0376 (7)	−0.0023 (5)	0.0016 (6)	0.0112 (6)
O4	0.0257 (7)	0.0172 (7)	0.0407 (8)	0.0010 (5)	−0.0046 (5)	0.0067 (5)
O5	0.0434 (8)	0.0318 (8)	0.0586 (10)	−0.0166 (7)	−0.0216 (8)	0.0098 (8)
O6	0.0360 (8)	0.0290 (8)	0.0370 (8)	−0.0003 (6)	0.0101 (7)	0.0095 (7)
N1	0.0316 (9)	0.0344 (10)	0.0259 (9)	0.0013 (8)	0.0065 (7)	0.0060 (8)
C1	0.0261 (10)	0.0263 (11)	0.0236 (9)	0.0060 (8)	0.0068 (8)	0.0086 (8)
C2	0.0228 (9)	0.0174 (9)	0.0185 (8)	0.0020 (7)	−0.0004 (7)	0.0016 (7)
C3	0.0219 (9)	0.0206 (10)	0.0230 (9)	0.0042 (7)	0.0033 (7)	0.0056 (8)
C4	0.0202 (9)	0.0208 (10)	0.0270 (10)	−0.0003 (7)	0.0002 (7)	0.0055 (8)
C5	0.0204 (8)	0.0177 (9)	0.0221 (9)	0.0009 (7)	0.0041 (7)	0.0023 (7)
C6	0.0244 (9)	0.0252 (11)	0.0241 (9)	0.0013 (7)	−0.0009 (8)	0.0039 (8)
C7	0.0270 (9)	0.0245 (11)	0.0278 (10)	−0.0074 (7)	−0.0017 (8)	0.0022 (8)
C8	0.0346 (11)	0.0171 (10)	0.0268 (10)	−0.0030 (8)	0.0039 (8)	0.0059 (8)
C9	0.0376 (13)	0.0520 (16)	0.088 (2)	−0.0061 (11)	−0.0232 (13)	−0.0089 (14)
C10	0.0275 (10)	0.0313 (12)	0.0309 (11)	0.0007 (9)	0.0027 (8)	0.0025 (9)
C11	0.0423 (13)	0.0460 (14)	0.0388 (12)	−0.0020 (11)	0.0010 (11)	0.0196 (10)
C12	0.0726 (19)	0.0518 (17)	0.0433 (14)	0.0161 (14)	0.0234 (14)	0.0045 (13)

Geometric parameters (Å, º)

Mn1—O4^i	2.1145 (16)	C2—C5	1.500 (2)
Mn1—O1	2.1252 (14)	C3—C8	1.385 (3)
Mn1—O3^ii	2.1361 (13)	C3—C4	1.389 (2)
Mn1—O6	2.1670 (15)	C4—C5	1.395 (2)
Mn1—O2^iii	2.2101 (15)	C4—H4	0.9500
Mn1—O1^iii	2.583 (2)	C5—C6	1.399 (2)
O1—C1	1.267 (2)	C6—C7	1.385 (3)
O2—C1	1.242 (2)	C6—H6	0.9500
O2—Mn1^iv	2.2101 (15)	C7—C8	1.394 (3)
O3—C2	1.253 (2)	C8—H8	0.9500
O3—Mn1^v	2.1361 (13)	C9—H9A	0.9800
O4—C2	1.259 (2)	C9—H9B	0.9800
O4—Mn1^vi	2.1146 (16)	C9—H9C	0.9800
O5—C7	1.377 (2)	C10—H10	0.9500
O5—C9	1.398 (3)	C11—H11A	0.9800
O6—C10	1.229 (2)	C11—H11B	0.9800
N1—C10	1.315 (3)	C11—H11C	0.9800
N1—C11	1.446 (2)	C12—H12A	0.9800
N1—C12	1.456 (3)	C12—H12B	0.9800
C1—C3	1.508 (3)	C12—H12C	0.9800
O4^i—Mn1—O1	85.70 (5)	C5—C4—H4	120.0
O4^i—Mn1—O3^ii	130.77 (5)	C4—C5—C6	119.65 (16)
O1—Mn1—O3^ii	94.90 (6)	C4—C5—C2	121.43 (16)
O4^i—Mn1—O6	85.10 (5)	C6—C5—C2	118.83 (16)
O1—Mn1—O6	167.17 (6)	C7—C6—C5	119.83 (17)
O1^iii—Mn1—O3^ii	141.20 (7)	C7—C6—H6	120.1
O1^iii—Mn1—O1	105.09 (8)	C5—C6—H6	120.1
O3^ii—Mn1—O6	84.41 (6)	O5—C7—C6	124.06 (17)
O4^i—Mn1—O2^iii	137.07 (6)	O5—C7—C8	115.61 (17)
O1—Mn1—O2^iii	96.37 (6)	C6—C7—C8	120.32 (17)
O3^ii—Mn1—O2^iii	91.91 (6)	C3—C8—C7	119.89 (18)
O6—Mn1—O2^iii	96.46 (7)	C3—C8—H8	120.1
O1^iii—Mn1—O4^i	84.39 (8)	C7—C8—H8	120.1
O1^iii—Mn1—O2^iii	53.65 (8)	O5—C9—H9A	109.5
O1^iii—Mn1—O6	82.98 (8)	O5—C9—H9B	109.5
C1—O1—Mn1	132.94 (12)	H9A—C9—H9B	109.5
C1—O2—Mn1^iv	101.54 (13)	O5—C9—H9C	109.5
C2—O3—Mn1^v	137.94 (11)	H9A—C9—H9C	109.5
C2—O4—Mn1^vi	134.62 (12)	H9B—C9—H9C	109.5
C7—O5—C9	118.17 (17)	O6—C10—N1	125.28 (19)
C10—O6—Mn1	123.53 (13)	O6—C10—H10	117.4
C10—N1—C11	121.53 (17)	N1—C10—H10	117.4
C10—N1—C12	120.36 (17)	N1—C11—H11A	109.5
C11—N1—C12	118.05 (17)	N1—C11—H11B	109.5
O2—C1—O1	121.50 (18)	H11A—C11—H11B	109.5
O2—C1—C3	119.38 (18)	N1—C11—H11C	109.5
O1—C1—C3	119.09 (18)	H11A—C11—H11C	109.5
O3—C2—O4	125.78 (16)	H11B—C11—H11C	109.5
O3—C2—C5	117.48 (15)	N1—C12—H12A	109.5
O4—C2—C5	116.72 (15)	N1—C12—H12B	109.5
C8—C3—C4	120.18 (17)	H12A—C12—H12B	109.5
C8—C3—C1	119.33 (17)	N1—C12—H12C	109.5
C4—C3—C1	120.48 (17)	H12A—C12—H12C	109.5
C3—C4—C5	120.04 (17)	H12B—C12—H12C	109.5
C3—C4—H4	120.0
O4^i—Mn1—O1—C1	9.73 (17)	C1—C3—C4—C5	178.42 (16)
O3^ii—Mn1—O1—C1	140.34 (17)	C3—C4—C5—C6	−0.4 (3)
O6—Mn1—O1—C1	54.0 (3)	C3—C4—C5—C2	176.12 (16)
O2^iii—Mn1—O1—C1	−127.19 (18)	O3—C2—C5—C4	−22.9 (2)
O4^i—Mn1—O6—C10	159.35 (16)	O4—C2—C5—C4	158.63 (17)
O1—Mn1—O6—C10	115.0 (3)	O3—C2—C5—C6	153.65 (17)
O3^ii—Mn1—O6—C10	27.52 (16)	O4—C2—C5—C6	−24.8 (2)
O2^iii—Mn1—O6—C10	−63.77 (17)	C4—C5—C6—C7	2.3 (3)
Mn1^iv—O2—C1—O1	−1.2 (2)	C2—C5—C6—C7	−174.30 (16)
Mn1^iv—O2—C1—C3	176.64 (13)	C9—O5—C7—C6	17.2 (3)
Mn1—O1—C1—O2	−107.6 (2)	C9—O5—C7—C8	−164.0 (2)
Mn1—O1—C1—C3	74.6 (2)	C5—C6—C7—O5	177.07 (17)
Mn1^v—O3—C2—O4	16.2 (3)	C5—C6—C7—C8	−1.6 (3)
Mn1^v—O3—C2—C5	−162.08 (13)	C4—C3—C8—C7	2.9 (3)
Mn1^vi—O4—C2—O3	21.3 (3)	C1—C3—C8—C7	−177.73 (16)
Mn1^vi—O4—C2—C5	−160.37 (12)	O5—C7—C8—C3	−179.77 (17)
O2—C1—C3—C8	−174.56 (19)	C6—C7—C8—C3	−0.9 (3)
O1—C1—C3—C8	3.4 (3)	Mn1—O6—C10—N1	−173.03 (15)
O2—C1—C3—C4	4.8 (3)	C11—N1—C10—O6	179.18 (19)
O1—C1—C3—C4	−177.25 (17)	C12—N1—C10—O6	−3.6 (3)
C8—C3—C4—C5	−2.2 (3)

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