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In the title mol­ecule, C12H8N2O7S, there are weak C-H...O interactions which generate rings of motifs S(5), R21(5), R12(4) and R12(8).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018191/ci6265sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018191/ci6265Isup2.hkl
Contains datablock I

CCDC reference: 222904

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.070
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - N1 = 5.66 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.11 From the CIF: _reflns_number_total 2832 Count of symmetry unique reflns 1602 Completeness (_total/calc) 176.78% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1230 Fraction of Friedel pairs measured 0.768 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989) and in many other fields (Spungin et al., 1992; Tharakan et al., 1992; Alford et al., 1991; Jiang et al., 1990; Narayanan & Krakow, 1983). The molecular and crystal structure of 3-nitrobenzenesulfonyl chloride has been recently reported (Vembu, Nallu, Spencer & Howard, 2003c). In view of the biological importance of its analogues and also to comapre its structural parameters with those of its precursor, 3-nitrobenzenesulfonyl chloride, an X-ray study of the title compound, (I), was undertaken.

The molecular structure of (I) shown in Fig. 1 and selected geometric parameters are given in Table 1. Atoms N1, O1 and O2 deviate from the mean plane formed by atoms C1–C6 by 0.031 (3), 0.015 (4) and 0.085 (4) Å, respectively. Atoms N2, O6, O7 deviate from the mean plane formed by atoms C7–C12 by 0.146 (3), 0.874 (4) and −0.456 (4) Å, respectively. The dihedral angle between the abovementioned planes is 39.68 (8)°. This shows their non-coplanar orientation, similar to that reported for other aromatic sulfonates (Vembu, Nallu, Garrison & Youngs, 2003b,c,d,e; Vembu, Nallu, Spencer & Howard, 2003a,b,d,e), and in contrast to the near coplanar orientation found in 2,4-dinitrophenyl 4-toluenesulfonate (Vembu, Nallu, Garrison & Youngs, 2003a) and 4-methoxyphenyl 4-toluenesulfonate (Vembu, Nallu, Garrison, Hindi & Youngs, 2003).

The crystal structure is stabilized by weak C—H···O interactions (Table 2). The range of H···O distances found in (I) agrees with that found for weak C—H···O bonds (Desiraju & Steiner, 1999). As shown in Fig. 2, each of the C2—H2···O1, C4—H4···O3, C6—H6···O2, C6—H6···O4 and C11—H11···O7 interactions generates a S(5) graph-set motif (Bernstein et al., 1995; Etter, 1990). The C6—H6···O2 and C6—H6···O4 interactions constitute a pair of bifurcated donor bonds. As seen in Fig. 3, the C8—H8···O4i and C9—H9···O4i interactions constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C3—H3···O6ii and C3—H3···O4ii interactions constitute a pair of bifurcated donor bonds generating an R12(8) motif. The C3—H3···O4ii and C4—H4···O4ii interactions constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C3—H3···O4ii and C3—H3···O5ii interactions constitute a pair of bifurcated donor bonds generating a symmetrical hydrogen-bonded chelate motif of graph-set R12(4). The C9—H9···O2ii and C10—H10···O2ii interactions together form a pair of bifurcated acceptor bonds generating an R21(5) motif. The C10—H10···O1iii and C11—H11···O1iii interactions together constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C2—H2···O6i and C11—H11···O6iv interactions also contribute for the supramolecular aggregation of the title compound (Fig. 4).

Experimental top

3-Nitrobenzenesulfonyl chloride (4.9 mmol) dissolved in acetone (5 ml) was added to 2-nitrophenol (5.0 mmol) in NaOH (4 ml, 5%) and shaken well. The crude title compound (2.6 mmol, yield: 53%) was precipitated from solution. Diffraction quality crystals were obtained by recrystallizing the crude product from aqueous ethanol.

Refinement top

All H atoms were located from difference Fourier maps and their positional parameters were refined, with Uiso = 1.2Ueq(parent atom). The C—H bond lengths are in the range 0.91 (2)–1.03 (2) Å.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Diagram showing hydrogen bonds 1–5 (the numbers correspond to sequence of entries in Table 2).
[Figure 3] Fig. 3. Diagram showing hydrogen bonds 6–17 (the numbers correspond to sequence of entries in Table 2). Symmetry codes are as in Table 2.
[Figure 4] Fig. 4. The packing of the molecules in the unit cell, viewed along the c axis, showing the network of hydrogen bonds.
2-Nitrophenyl 3-nitrobenzenesulfonate top
Crystal data top
C12H8N2O7SDx = 1.654 Mg m3
Mr = 324.26Melting point = 358–360 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2719 reflections
a = 19.9671 (8) Åθ = 2.6–26.7°
b = 12.7083 (5) ŵ = 0.29 mm1
c = 5.1306 (2) ÅT = 120 K
V = 1301.88 (9) Å3Block, colourless
Z = 40.14 × 0.12 × 0.08 mm
F(000) = 664
Data collection top
Bruker SMART CCD 6K area-detector
diffractometer
2355 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 27.1°, θmin = 1.9°
Detector resolution: 8 pixels mm-1h = 2425
ω scansk = 1615
9331 measured reflectionsl = 66
2832 independent 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)] = 0.034Only H-atom coordinates refined
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0332P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
2832 reflectionsΔρmax = 0.18 e Å3
223 parametersΔρmin = 0.33 e Å3
1 restraintAbsolute structure: (Flack, 1983), 1230 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.10 (7)
Crystal data top
C12H8N2O7SV = 1301.88 (9) Å3
Mr = 324.26Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 19.9671 (8) ŵ = 0.29 mm1
b = 12.7083 (5) ÅT = 120 K
c = 5.1306 (2) Å0.14 × 0.12 × 0.08 mm
Data collection top
Bruker SMART CCD 6K area-detector
diffractometer
2355 reflections with I > 2σ(I)
9331 measured reflectionsRint = 0.059
2832 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034Only H-atom coordinates refined
wR(F2) = 0.070Δρmax = 0.18 e Å3
S = 0.96Δρmin = 0.33 e Å3
2832 reflectionsAbsolute structure: (Flack, 1983), 1230 Friedel pairs
223 parametersAbsolute structure parameter: 0.10 (7)
1 restraint
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
xyzUiso*/Ueq
C10.10099 (11)0.59508 (17)0.7938 (5)0.0226 (5)
C20.09759 (12)0.68560 (18)0.6474 (5)0.0263 (5)
H20.0626 (12)0.7325 (19)0.674 (5)0.032*
C30.14536 (12)0.70336 (18)0.4570 (5)0.0290 (6)
H30.1449 (12)0.7663 (19)0.347 (5)0.035*
C40.19539 (12)0.62919 (18)0.4122 (5)0.0270 (5)
H40.2278 (12)0.6363 (19)0.279 (5)0.032*
C50.19640 (10)0.53812 (16)0.5619 (4)0.0219 (5)
C60.14998 (10)0.51890 (17)0.7576 (4)0.0210 (5)
H60.1521 (11)0.4514 (17)0.869 (5)0.025*
C70.35510 (10)0.57182 (16)0.6233 (4)0.0206 (5)
C80.34033 (11)0.66443 (18)0.7508 (5)0.0253 (5)
H80.3064 (12)0.6656 (17)0.885 (5)0.030*
C90.37541 (11)0.75507 (18)0.6868 (5)0.0275 (5)
H90.3655 (12)0.818 (2)0.779 (5)0.033*
C100.42276 (10)0.75352 (17)0.4901 (6)0.0258 (5)
H100.4449 (11)0.8149 (19)0.441 (5)0.031*
C110.43749 (11)0.66092 (18)0.3604 (5)0.0239 (5)
H110.4698 (12)0.6597 (17)0.235 (5)0.029*
C120.40411 (10)0.57001 (16)0.4328 (4)0.0204 (5)
S10.25954 (2)0.44364 (4)0.50573 (12)0.02233 (12)
O10.00775 (8)0.64556 (11)1.0301 (4)0.0348 (4)
O20.05613 (8)0.49898 (12)1.1363 (3)0.0321 (4)
O30.28079 (8)0.45294 (12)0.2416 (3)0.0293 (4)
O40.24002 (7)0.34518 (12)0.6120 (3)0.0277 (4)
O50.31924 (7)0.48061 (11)0.6923 (3)0.0225 (3)
O60.42793 (8)0.39240 (12)0.4488 (3)0.0332 (4)
O70.44083 (8)0.47339 (13)0.0786 (3)0.0340 (4)
N10.05125 (8)0.57834 (14)1.0011 (4)0.0261 (4)
N20.42532 (8)0.47095 (15)0.3104 (4)0.0247 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0213 (11)0.0237 (12)0.0229 (12)0.0054 (9)0.0008 (10)0.0047 (9)
C20.0271 (11)0.0213 (12)0.0305 (14)0.0014 (9)0.0046 (11)0.0024 (10)
C30.0331 (12)0.0222 (12)0.0318 (16)0.0029 (9)0.0016 (12)0.0047 (10)
C40.0262 (12)0.0313 (13)0.0234 (12)0.0065 (10)0.0001 (10)0.0051 (10)
C50.0212 (10)0.0217 (11)0.0228 (13)0.0018 (8)0.0046 (9)0.0016 (8)
C60.0213 (10)0.0197 (11)0.0220 (12)0.0034 (8)0.0028 (10)0.0009 (10)
C70.0185 (10)0.0243 (12)0.0189 (11)0.0011 (8)0.0050 (9)0.0040 (9)
C80.0224 (11)0.0319 (14)0.0216 (12)0.0006 (9)0.0045 (10)0.0012 (10)
C90.0282 (11)0.0240 (12)0.0303 (13)0.0016 (9)0.0005 (11)0.0061 (11)
C100.0212 (10)0.0236 (11)0.0326 (12)0.0023 (8)0.0002 (12)0.0022 (12)
C110.0201 (11)0.0285 (13)0.0231 (12)0.0020 (9)0.0036 (10)0.0022 (10)
C120.0187 (10)0.0217 (11)0.0207 (13)0.0042 (8)0.0020 (9)0.0016 (8)
S10.0208 (2)0.0247 (3)0.0215 (2)0.0013 (2)0.0002 (3)0.0018 (3)
O10.0314 (8)0.0342 (9)0.0389 (10)0.0074 (7)0.0056 (9)0.0076 (9)
O20.0351 (9)0.0296 (9)0.0318 (9)0.0017 (7)0.0097 (8)0.0048 (8)
O30.0267 (8)0.0404 (10)0.0209 (9)0.0005 (7)0.0009 (7)0.0045 (7)
O40.0265 (8)0.0225 (8)0.0340 (9)0.0003 (6)0.0003 (8)0.0024 (6)
O50.0226 (7)0.0242 (8)0.0205 (8)0.0044 (6)0.0010 (7)0.0030 (6)
O60.0344 (9)0.0207 (8)0.0444 (13)0.0043 (6)0.0065 (8)0.0020 (8)
O70.0285 (9)0.0438 (10)0.0299 (11)0.0031 (7)0.0064 (8)0.0103 (8)
N10.0269 (9)0.0273 (10)0.0241 (9)0.0020 (7)0.0010 (11)0.0083 (10)
N20.0165 (9)0.0264 (11)0.0313 (12)0.0000 (7)0.0003 (9)0.0070 (9)
Geometric parameters (Å, º) top
C1—C21.376 (3)C8—H80.97 (2)
C1—C61.389 (3)C9—C101.383 (3)
C1—N11.471 (3)C9—H90.95 (3)
C2—C31.384 (3)C10—C111.383 (3)
C2—H20.93 (2)C10—H100.93 (2)
C3—C41.393 (3)C11—C121.384 (3)
C3—H30.98 (3)C11—H110.91 (2)
C4—C51.389 (3)C12—N21.469 (3)
C4—H40.94 (3)S1—O41.4195 (16)
C5—C61.388 (3)S1—O31.4250 (16)
C5—S11.765 (2)S1—O51.5992 (16)
C6—H61.03 (2)O1—N11.227 (2)
C7—C81.378 (3)O2—N11.228 (2)
C7—C121.383 (3)O6—N21.226 (2)
C7—O51.408 (2)O7—N21.229 (3)
C8—C91.388 (3)
C2—C1—C6123.0 (2)C10—C9—H9121.2 (15)
C2—C1—N1118.9 (2)C8—C9—H9118.4 (15)
C6—C1—N1118.13 (19)C9—C10—C11120.5 (2)
C1—C2—C3119.2 (2)C9—C10—H10120.6 (15)
C1—C2—H2119.6 (16)C11—C10—H10118.9 (15)
C3—C2—H2121.2 (16)C10—C11—C12118.6 (2)
C2—C3—C4120.0 (2)C10—C11—H11120.3 (15)
C2—C3—H3122.3 (15)C12—C11—H11121.0 (14)
C4—C3—H3117.7 (15)C7—C12—C11121.07 (19)
C5—C4—C3118.9 (2)C7—C12—N2121.34 (18)
C5—C4—H4117.9 (15)C11—C12—N2117.49 (19)
C3—C4—H4123.1 (15)O4—S1—O3121.34 (10)
C6—C5—C4122.5 (2)O4—S1—O5103.53 (9)
C6—C5—S1118.39 (16)O3—S1—O5108.83 (9)
C4—C5—S1119.14 (17)O4—S1—C5109.93 (9)
C5—C6—C1116.4 (2)O3—S1—C5108.15 (10)
C5—C6—H6121.3 (13)O5—S1—C5103.59 (9)
C1—C6—H6122.3 (13)C7—O5—S1118.08 (13)
C8—C7—C12120.06 (19)O1—N1—O2124.0 (2)
C8—C7—O5118.36 (19)O1—N1—C1117.7 (2)
C12—C7—O5121.58 (18)O2—N1—C1118.28 (16)
C7—C8—C9119.2 (2)O6—N2—O7124.76 (19)
C7—C8—H8120.1 (14)O6—N2—C12117.54 (18)
C9—C8—H8120.7 (14)O7—N2—C12117.67 (19)
C10—C9—C8120.4 (2)
C6—C1—C2—C30.9 (3)C10—C11—C12—N2174.1 (2)
N1—C1—C2—C3178.1 (2)C6—C5—S1—O419.79 (19)
C1—C2—C3—C41.2 (3)C4—C5—S1—O4161.09 (17)
C2—C3—C4—C50.2 (3)C6—C5—S1—O3154.30 (16)
C3—C4—C5—C61.1 (3)C4—C5—S1—O326.6 (2)
C3—C4—C5—S1179.86 (18)C6—C5—S1—O590.30 (17)
C4—C5—C6—C11.3 (3)C4—C5—S1—O588.81 (18)
S1—C5—C6—C1179.63 (16)C8—C7—O5—S1101.3 (2)
C2—C1—C6—C50.3 (3)C12—C7—O5—S178.7 (2)
N1—C1—C6—C5179.35 (18)O4—S1—O5—C7173.34 (15)
C12—C7—C8—C90.4 (3)O3—S1—O5—C743.00 (16)
O5—C7—C8—C9179.6 (2)C5—S1—O5—C771.90 (16)
C7—C8—C9—C102.6 (3)C2—C1—N1—O11.6 (3)
C8—C9—C10—C112.2 (4)C6—C1—N1—O1179.3 (2)
C9—C10—C11—C120.3 (4)C2—C1—N1—O2177.6 (2)
C8—C7—C12—C112.2 (3)C6—C1—N1—O21.5 (3)
O5—C7—C12—C11177.80 (19)C7—C12—N2—O636.8 (3)
C8—C7—C12—N2174.3 (2)C11—C12—N2—O6139.80 (19)
O5—C7—C12—N25.7 (3)C7—C12—N2—O7145.0 (2)
C10—C11—C12—C72.5 (3)C11—C12—N2—O738.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.93 (2)2.40 (3)2.708 (3)99.2 (18)
C4—H4···O30.94 (3)2.57 (2)2.948 (3)104.5 (17)
C6—H6···O21.03 (2)2.43 (2)2.711 (3)94.2 (14)
C6—H6···O41.03 (2)2.58 (2)2.944 (3)100.4 (16)
C11—H11···O70.91 (2)2.57 (2)2.788 (3)94.4 (16)
C8—H8···O4i0.97 (2)2.72 (2)3.359 (3)123.8 (17)
C9—H9···O4i0.95 (3)2.73 (3)3.374 (3)125.3 (18)
C2—H2···O6i0.93 (2)2.48 (2)3.092 (3)123.5 (18)
C3—H3···O6ii0.98 (3)2.98 (3)3.836 (3)147.1 (19)
C3—H3···O4ii0.98 (3)2.78 (3)3.409 (3)122.5 (18)
C9—H9···O2ii0.95 (3)2.88 (2)3.398 (3)115.6 (18)
C4—H4···O4ii0.94 (3)2.86 (2)3.401 (3)117.3 (18)
C10—H10···O2ii0.93 (2)2.54 (2)3.236 (3)131.4 (18)
C3—H3···O5ii0.98 (3)2.93 (2)3.842 (3)156 (2)
C10—H10···O1iii0.93 (2)2.51 (2)3.177 (3)129.2 (19)
C11—H11···O1iii0.91 (2)2.79 (2)3.300 (3)116.2 (17)
C11—H11···O6iv0.91 (2)2.60 (2)3.484 (3)163.5 (19)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1/2, y+3/2, z1; (iv) x+1, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC12H8N2O7S
Mr324.26
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)120
a, b, c (Å)19.9671 (8), 12.7083 (5), 5.1306 (2)
V3)1301.88 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.14 × 0.12 × 0.08
Data collection
DiffractometerBruker SMART CCD 6K area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9331, 2832, 2355
Rint0.059
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.070, 0.96
No. of reflections2832
No. of parameters223
No. of restraints1
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.18, 0.33
Absolute structure(Flack, 1983), 1230 Friedel pairs
Absolute structure parameter0.10 (7)

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Sheldrick, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
C1—N11.471 (3)S1—O51.5992 (16)
C5—S11.765 (2)O1—N11.227 (2)
C7—O51.408 (2)O2—N11.228 (2)
C12—N21.469 (3)O6—N21.226 (2)
S1—O41.4195 (16)O7—N21.229 (3)
S1—O31.4250 (16)
O4—S1—O3121.34 (10)O1—N1—O2124.0 (2)
O4—S1—O5103.53 (9)O1—N1—C1117.7 (2)
O3—S1—O5108.83 (9)O2—N1—C1118.28 (16)
O4—S1—C5109.93 (9)O6—N2—O7124.76 (19)
O3—S1—C5108.15 (10)O6—N2—C12117.54 (18)
O5—S1—C5103.59 (9)O7—N2—C12117.67 (19)
C7—O5—S1118.08 (13)
C5—S1—O5—C771.90 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.93 (2)2.40 (3)2.708 (3)99.2 (18)
C4—H4···O30.94 (3)2.57 (2)2.948 (3)104.5 (17)
C6—H6···O21.03 (2)2.43 (2)2.711 (3)94.2 (14)
C6—H6···O41.03 (2)2.58 (2)2.944 (3)100.4 (16)
C11—H11···O70.91 (2)2.57 (2)2.788 (3)94.4 (16)
C8—H8···O4i0.97 (2)2.72 (2)3.359 (3)123.8 (17)
C9—H9···O4i0.95 (3)2.73 (3)3.374 (3)125.3 (18)
C2—H2···O6i0.93 (2)2.48 (2)3.092 (3)123.5 (18)
C3—H3···O6ii0.98 (3)2.98 (3)3.836 (3)147.1 (19)
C3—H3···O4ii0.98 (3)2.78 (3)3.409 (3)122.5 (18)
C9—H9···O2ii0.95 (3)2.88 (2)3.398 (3)115.6 (18)
C4—H4···O4ii0.94 (3)2.86 (2)3.401 (3)117.3 (18)
C10—H10···O2ii0.93 (2)2.54 (2)3.236 (3)131.4 (18)
C3—H3···O5ii0.98 (3)2.93 (2)3.842 (3)156 (2)
C10—H10···O1iii0.93 (2)2.51 (2)3.177 (3)129.2 (19)
C11—H11···O1iii0.91 (2)2.79 (2)3.300 (3)116.2 (17)
C11—H11···O6iv0.91 (2)2.60 (2)3.484 (3)163.5 (19)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1/2, y+3/2, z1; (iv) x+1, y+1, z1/2.
 

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