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The title mol­ecule, C12H11N3O4, is essentially planar, the r.m.s. deviation for all non-H atoms being 0.068 Å. An intra­molecular C—H...N hydrogen bond occurs. The crystal packing is dominated by π–π inter­actions [shortest centroid–centroid distance = 3.6312 (16) Å], which lead to supra­molecular chains that are linked into a three-dimensional network via C—H...O contacts. The crystal was found to be a non-merohedral twin (twin law −1 0 0/0 −1 0/ 0.784 0 1), the fractional contribution of the minor component being approx­imately 22%.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810018635/ez2209sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810018635/ez2209Isup2.hkl
Contains datablock I

CCDC reference: 781416

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.065
  • wR factor = 0.220
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
Alert level G PLAT931_ALERT_5_G Check Twin Law ( 0 0 1)[ ] Estimated BASF 0.27 PLAT931_ALERT_5_G Check Twin Law ( )[ 2 0 5] Estimated BASF 0.27
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: The contribution of the authors to this submission is as follows:
 Gilberto A. Romeiro            co-supervisor
 Carlos M. R. Ribeiro           student
 Solange M. S. V.Wardell        co-supervisor
 James L. Wardell               spectroscopist and co-responsible for write-up
 Ng Seik Weng                   final crystallography
 Edward R. T. Tiekink           crystallography and co-responsible for write-up


1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

The preparations of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives have been reported using the Vilsmeier-Haack reactions (Meth-Cohn & Stanforth, 1991) of acylaminoacetanilides with POCl3 and DMF (Singh & Singh, 1994; Takahashi & Izawa, 2005; Singh et al., 1994; Kmetic & Stanovnik, 1995). The compounds have been used as precursors of 4-hydroxymethylene-2-aryl-2-oxazolin-5-one, which have been tested for anti-bacterial activities (Singh & Singh, 2008). The crystal structures of 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and 4-(N,N-dimethylaminomethylene)-2-(2-nitrophenyl)-2-oxazolin-5-one (Vijayalakshmi et al., 1998) have been reported. We now report the crystal structure of 4-(N,N-dimethylaminomethylene)-2-(4-nitrophenyl)-2-oxazolin-5-one, (I).

The molecule of (I), Fig. 1, is essentially planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.157 (4) Å for atom C5 and -0.158 (3) for atom O4; the r.m.s. = 0.068 Å. The sequence of C1–N1, N1–C2, C2–C4, and C4–N2 bond distances of 1.289 (4), 1.398 (4), 1.382 (5), and 1.317 (4) Å, respectively, indicate substantial delocalisation of π-electron density over these atoms. The geometric parameters in (I) match closely those found in the parent compound, namely 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and in the 2-nitro derivative (Vijayalakshmi et al., 1998).

The crystal packing is dominated by C–H···O and ππ interactions; the N1 atom of the oxazolin-5-one is involved in an intramolecular C–H···N contact that shields this atom from forming intermolecular interactions, Table 1. Columns of molecules orientated along the b axis are stabilised by ππ contacts with the shortest of these occurring between centrosymmetrically related benzene rings [ring centroid(C7–C12)···ring centroid(C7–C12)i = 3.6312 (16) Å for i: 1-x, 1-y, 2-z]. The benzene rings also form ππ interactions with the oxazolin-5-one rings [ring centroid(C7–C12)···ring centroid(O1,N1,C1–C3)ii = 3.7645 (17) Å for ii: 1-x, -y, 2-z] to form a supramolecular chain, Fig. 2. The chains are connected by a series of C–H···O contacts, Table 1, to form a 3-D network, Fig. 3.

Related literature top

For the synthesis, synthetic uses and properties of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives, see: Singh & Singh (1994, 2008); Takahashi & Izawa (2005); Singh et al. (1994); Kmetic & Stanovnik (1995). For the Vilsmeier–Haack reaction, see: Meth-Cohn & Stanforth (1991). For related structures, see Vasuki et al. (2002); Vijayalakshmi et al. (1998). For the treatment of twinned diffraction data, see: Spek (2009).

Experimental top

The title compound was prepared as per published procedures (Singh & Singh, 1994; Singh et al., 1994). Physical properties were in agreement with published data. The crystal used in the structure determination was grown from EtOH solution.

Refinement top

The C-bound H atoms were geometrically placed (C–H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). For the treatment of twinned diffraction data, see: Spek (2009).

Structure description top

The preparations of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives have been reported using the Vilsmeier-Haack reactions (Meth-Cohn & Stanforth, 1991) of acylaminoacetanilides with POCl3 and DMF (Singh & Singh, 1994; Takahashi & Izawa, 2005; Singh et al., 1994; Kmetic & Stanovnik, 1995). The compounds have been used as precursors of 4-hydroxymethylene-2-aryl-2-oxazolin-5-one, which have been tested for anti-bacterial activities (Singh & Singh, 2008). The crystal structures of 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and 4-(N,N-dimethylaminomethylene)-2-(2-nitrophenyl)-2-oxazolin-5-one (Vijayalakshmi et al., 1998) have been reported. We now report the crystal structure of 4-(N,N-dimethylaminomethylene)-2-(4-nitrophenyl)-2-oxazolin-5-one, (I).

The molecule of (I), Fig. 1, is essentially planar with the maximum deviations from the least-squares plane through all non-hydrogen atoms being 0.157 (4) Å for atom C5 and -0.158 (3) for atom O4; the r.m.s. = 0.068 Å. The sequence of C1–N1, N1–C2, C2–C4, and C4–N2 bond distances of 1.289 (4), 1.398 (4), 1.382 (5), and 1.317 (4) Å, respectively, indicate substantial delocalisation of π-electron density over these atoms. The geometric parameters in (I) match closely those found in the parent compound, namely 4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one (Vasuki et al., 2002) and in the 2-nitro derivative (Vijayalakshmi et al., 1998).

The crystal packing is dominated by C–H···O and ππ interactions; the N1 atom of the oxazolin-5-one is involved in an intramolecular C–H···N contact that shields this atom from forming intermolecular interactions, Table 1. Columns of molecules orientated along the b axis are stabilised by ππ contacts with the shortest of these occurring between centrosymmetrically related benzene rings [ring centroid(C7–C12)···ring centroid(C7–C12)i = 3.6312 (16) Å for i: 1-x, 1-y, 2-z]. The benzene rings also form ππ interactions with the oxazolin-5-one rings [ring centroid(C7–C12)···ring centroid(O1,N1,C1–C3)ii = 3.7645 (17) Å for ii: 1-x, -y, 2-z] to form a supramolecular chain, Fig. 2. The chains are connected by a series of C–H···O contacts, Table 1, to form a 3-D network, Fig. 3.

For the synthesis, synthetic uses and properties of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-one derivatives, see: Singh & Singh (1994, 2008); Takahashi & Izawa (2005); Singh et al. (1994); Kmetic & Stanovnik (1995). For the Vilsmeier–Haack reaction, see: Meth-Cohn & Stanforth (1991). For related structures, see Vasuki et al. (2002); Vijayalakshmi et al. (1998). For the treatment of twinned diffraction data, see: Spek (2009).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A view of the supramolecular chain aligned along the b axis in (I) sustained by ππ intercations (purple dashed lines). Colour code: O, red; N, blue; C, grey; and H, green.
[Figure 3] Fig. 3. View of the connections between chains in (I) with the C–H···O interactions shown as orange dashed lines. Colour code: O, red; N, blue; C, grey; and H, green.
4-[(Dimethylamino)methylidene]-2-(4-nitrophenyl)-1,3-oxazol-5(4H)-one top
Crystal data top
C12H11N3O4F(000) = 544
Mr = 261.24Dx = 1.531 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2714 reflections
a = 9.5313 (2) Åθ = 2.9–27.5°
b = 9.5204 (3) ŵ = 0.12 mm1
c = 13.0349 (4) ÅT = 120 K
β = 106.661 (2)°Block, red
V = 1133.15 (6) Å30.42 × 0.38 × 0.22 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2581 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2030 reflections with I > 2σ(I)
10 cm confocal mirrors monochromatorRint = 0.071
Detector resolution: 9.091 pixels mm-1θmax = 27.4°, θmin = 3.1°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
k = 1211
Tmin = 0.661, Tmax = 1.000l = 1616
14210 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.220 w = 1/[σ2(Fo2) + (0.0936P)2 + 1.6594P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max = 0.001
2581 reflectionsΔρmax = 0.33 e Å3
176 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (5)
Crystal data top
C12H11N3O4V = 1133.15 (6) Å3
Mr = 261.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.5313 (2) ŵ = 0.12 mm1
b = 9.5204 (3) ÅT = 120 K
c = 13.0349 (4) Å0.42 × 0.38 × 0.22 mm
β = 106.661 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2581 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
2030 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 1.000Rint = 0.071
14210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.220H-atom parameters constrained
S = 1.19Δρmax = 0.33 e Å3
2581 reflectionsΔρmin = 0.30 e Å3
176 parameters
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.

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 > 2σ(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
xyzUiso*/Ueq
O10.3806 (2)0.5986 (2)0.33548 (17)0.0197 (5)
O20.2556 (3)0.4481 (2)0.20576 (17)0.0239 (6)
O30.8419 (3)1.1001 (3)0.6327 (2)0.0324 (6)
O40.7443 (3)1.0746 (3)0.76142 (19)0.0307 (6)
N10.2875 (3)0.5457 (3)0.4711 (2)0.0180 (6)
N20.0528 (3)0.3059 (3)0.4441 (2)0.0203 (6)
N30.7556 (3)1.0430 (3)0.6733 (2)0.0209 (6)
C10.3786 (3)0.6220 (3)0.4393 (2)0.0166 (6)
C20.2186 (3)0.4617 (3)0.3831 (2)0.0179 (6)
C30.2761 (3)0.4921 (3)0.2958 (2)0.0195 (7)
C40.1130 (3)0.3590 (3)0.3735 (2)0.0189 (7)
H40.07780.31990.30380.023*
C50.0939 (4)0.3462 (4)0.5569 (3)0.0237 (7)
H5A0.13780.26550.60120.036*
H5B0.00660.37680.57610.036*
H5C0.16490.42330.56910.036*
C60.0548 (4)0.1947 (4)0.4138 (3)0.0284 (8)
H6A0.07800.17780.33660.043*
H6B0.14400.22230.43170.043*
H6C0.01520.10860.45260.043*
C70.4765 (3)0.7290 (3)0.4994 (2)0.0168 (6)
C80.4797 (3)0.7571 (3)0.6051 (2)0.0184 (6)
H80.41840.70560.63750.022*
C90.5715 (3)0.8590 (3)0.6624 (2)0.0185 (6)
H90.57350.87940.73420.022*
C100.6608 (3)0.9314 (3)0.6135 (2)0.0178 (6)
C110.6608 (3)0.9058 (3)0.5089 (2)0.0173 (6)
H110.72310.95710.47720.021*
C120.5676 (3)0.8035 (3)0.4519 (2)0.0175 (6)
H120.56550.78380.38000.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0239 (12)0.0203 (11)0.0177 (11)0.0022 (9)0.0105 (9)0.0010 (8)
O20.0307 (13)0.0242 (12)0.0187 (11)0.0017 (10)0.0100 (10)0.0029 (9)
O30.0323 (14)0.0382 (15)0.0291 (13)0.0147 (12)0.0127 (11)0.0044 (11)
O40.0397 (15)0.0328 (14)0.0219 (12)0.0061 (12)0.0125 (11)0.0075 (10)
N10.0195 (13)0.0171 (12)0.0183 (13)0.0003 (10)0.0067 (10)0.0004 (10)
N20.0209 (13)0.0163 (13)0.0248 (13)0.0015 (11)0.0082 (11)0.0025 (10)
N30.0219 (13)0.0210 (13)0.0195 (13)0.0017 (12)0.0056 (11)0.0024 (11)
C10.0193 (14)0.0179 (14)0.0143 (13)0.0046 (12)0.0073 (11)0.0029 (11)
C20.0198 (15)0.0172 (14)0.0173 (14)0.0032 (12)0.0065 (12)0.0009 (11)
C30.0218 (15)0.0165 (14)0.0207 (15)0.0022 (12)0.0068 (12)0.0030 (12)
C40.0222 (16)0.0156 (14)0.0198 (15)0.0042 (12)0.0076 (12)0.0024 (11)
C50.0270 (17)0.0235 (16)0.0246 (16)0.0024 (14)0.0136 (14)0.0033 (13)
C60.0247 (17)0.0210 (16)0.039 (2)0.0050 (14)0.0077 (15)0.0059 (14)
C70.0182 (15)0.0145 (14)0.0185 (14)0.0035 (12)0.0062 (12)0.0022 (11)
C80.0201 (15)0.0188 (15)0.0184 (14)0.0018 (12)0.0089 (12)0.0040 (12)
C90.0215 (15)0.0193 (15)0.0158 (13)0.0052 (13)0.0070 (12)0.0030 (12)
C100.0174 (14)0.0152 (14)0.0198 (15)0.0025 (12)0.0036 (12)0.0005 (11)
C110.0180 (14)0.0175 (14)0.0178 (14)0.0023 (12)0.0073 (11)0.0035 (11)
C120.0193 (14)0.0184 (14)0.0169 (14)0.0029 (12)0.0086 (12)0.0014 (11)
Geometric parameters (Å, º) top
O1—C11.377 (3)C5—H5B0.9800
O1—C31.411 (4)C5—H5C0.9800
O2—C31.209 (4)C6—H6A0.9800
O3—N31.226 (4)C6—H6B0.9800
O4—N31.222 (4)C6—H6C0.9800
N1—C11.289 (4)C7—C81.394 (4)
N1—C21.398 (4)C7—C121.396 (4)
N2—C41.317 (4)C8—C91.375 (4)
N2—C61.448 (4)C8—H80.9500
N2—C51.460 (4)C9—C101.385 (4)
N3—C101.466 (4)C9—H90.9500
C1—C71.450 (4)C10—C111.385 (4)
C2—C41.382 (5)C11—C121.383 (4)
C2—C31.428 (4)C11—H110.9500
C4—H40.9500C12—H120.9500
C5—H5A0.9800
C1—O1—C3105.6 (2)H5B—C5—H5C109.5
C1—N1—C2105.0 (2)N2—C6—H6A109.5
C4—N2—C6120.5 (3)N2—C6—H6B109.5
C4—N2—C5123.9 (3)H6A—C6—H6B109.5
C6—N2—C5115.5 (3)N2—C6—H6C109.5
O4—N3—O3123.2 (3)H6A—C6—H6C109.5
O4—N3—C10118.1 (3)H6B—C6—H6C109.5
O3—N3—C10118.7 (3)C8—C7—C12120.0 (3)
N1—C1—O1115.2 (3)C8—C7—C1119.8 (3)
N1—C1—C7127.6 (3)C12—C7—C1120.2 (3)
O1—C1—C7117.2 (3)C9—C8—C7120.2 (3)
C4—C2—N1129.6 (3)C9—C8—H8119.9
C4—C2—C3120.5 (3)C7—C8—H8119.9
N1—C2—C3109.9 (3)C8—C9—C10118.7 (3)
O2—C3—O1120.4 (3)C8—C9—H9120.7
O2—C3—C2135.4 (3)C10—C9—H9120.7
O1—C3—C2104.3 (2)C11—C10—C9122.7 (3)
N2—C4—C2131.3 (3)C11—C10—N3118.5 (3)
N2—C4—H4114.4C9—C10—N3118.8 (3)
C2—C4—H4114.4C12—C11—C10118.1 (3)
N2—C5—H5A109.5C12—C11—H11120.9
N2—C5—H5B109.5C10—C11—H11120.9
H5A—C5—H5B109.5C11—C12—C7120.4 (3)
N2—C5—H5C109.5C11—C12—H12119.8
H5A—C5—H5C109.5C7—C12—H12119.8
C2—N1—C1—O10.3 (3)O1—C1—C7—C8179.8 (3)
C2—N1—C1—C7179.1 (3)N1—C1—C7—C12179.3 (3)
C3—O1—C1—N10.1 (3)O1—C1—C7—C120.1 (4)
C3—O1—C1—C7179.5 (3)C12—C7—C8—C90.6 (5)
C1—N1—C2—C4178.8 (3)C1—C7—C8—C9179.5 (3)
C1—N1—C2—C30.5 (3)C7—C8—C9—C100.7 (5)
C1—O1—C3—O2178.9 (3)C8—C9—C10—C110.4 (5)
C1—O1—C3—C20.4 (3)C8—C9—C10—N3178.2 (3)
C4—C2—C3—O20.1 (6)O4—N3—C10—C11172.7 (3)
N1—C2—C3—O2178.6 (4)O3—N3—C10—C117.1 (4)
C4—C2—C3—O1179.1 (3)O4—N3—C10—C95.1 (4)
N1—C2—C3—O10.6 (3)O3—N3—C10—C9175.0 (3)
C6—N2—C4—C2178.4 (3)C9—C10—C11—C120.1 (5)
C5—N2—C4—C22.4 (5)N3—C10—C11—C12177.9 (3)
N1—C2—C4—N23.9 (6)C10—C11—C12—C70.1 (4)
C3—C2—C4—N2174.2 (3)C8—C7—C12—C110.3 (4)
N1—C1—C7—C80.9 (5)C1—C7—C12—C11179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5c···N10.982.283.074 (5)137
C5—H5a···O2i0.982.533.504 (4)177
C5—H5c···O4ii0.982.573.259 (5)127
C9—H9···O1iii0.952.563.304 (4)135
C11—H11···O2iv0.952.453.144 (4)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H11N3O4
Mr261.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)9.5313 (2), 9.5204 (3), 13.0349 (4)
β (°) 106.661 (2)
V3)1133.15 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.42 × 0.38 × 0.22
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.661, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14210, 2581, 2030
Rint0.071
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.220, 1.19
No. of reflections2581
No. of parameters176
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.30

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5c···N10.982.283.074 (5)137
C5—H5a···O2i0.982.533.504 (4)177
C5—H5c···O4ii0.982.573.259 (5)127
C9—H9···O1iii0.952.563.304 (4)135
C11—H11···O2iv0.952.453.144 (4)130
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y+1/2, z+1/2.
 

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