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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3038.
Published online 2009 November 7. doi:  10.1107/S1600536809046005
PMCID: PMC2971988

4-Nitro­phenyl 2-methyl­benzoate

Abstract

The title compound, C14H11NO4, crystallizes with two mol­ecules in the asymmetric unit. The major conformational difference between these two mol­ecules is the dihedral angle between the aromatic rings, namely 36.99 (5) and 55.04 (5)°. The nitro groups are coplanar with the phenyl rings to which they are attached, the O—N—C—C torsion angles being −1.9 (3) and 1.0 (3)° in the two mol­ecules.

Related literature

For background to the applications of aromatic esters containing nitro groups in their aromatic rings, see: Jefford & Zaslona (1985 [triangle]); Jefford et al. (1986 [triangle]); Schauble et al. (1971 [triangle]). For related structures, see: Adams & Morsi (1976 [triangle]); Shibakami & Sekiya (1995 [triangle]).

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Object name is e-65-o3038-scheme1.jpg

Experimental

Crystal data

  • C14H11NO4
  • M r = 257.24
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3038-efi1.jpg
  • a = 11.4748 (7) Å
  • b = 14.3608 (8) Å
  • c = 14.5944 (9) Å
  • V = 2405.0 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 173 K
  • 0.48 × 0.43 × 0.42 mm

Data collection

  • Stoe IPDS II two-circle diffractometer
  • Absorption correction: none
  • 8396 measured reflections
  • 2536 independent reflections
  • 2233 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.081
  • S = 1.00
  • 2536 reflections
  • 346 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046005/pv2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046005/pv2221Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the University Research Fund (URF 2008–09) for financial support. The Department of Chemistry, Quaid-I-Azam Universit, and the Institut für Anorganische Chemie J.-W.-Goethe-Universität Frankfurt, are thanked for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Aromatic esters containing nitro groups in their aromatic rings are potential precursors for the preparation of compounds with a number of biological activities such as analgesic and anti-inflammatory (Jefford & Zaslona, 1985). In addition, these compounds served as potential intermediates in the synthesis of many natural products (Jefford et al., 1986; Schauble et al., 1971). The nitro group can be reduced to amino group which can be utilized for the synthesis of azoxy compounds. We have synthsized the title compound (I) which is a nitro substituted ester. In this article, the crystal structure of (I) is reported.

The title compound crystallizes with two molecules (Fig. 1) in an asymmetric unit. The major conformational difference between the two molecules is the dihedral angle between the aromatic rings, namely 36.99 (5)° and 55.04 (5)°. The nitro groups in both molecules are coplanar with the phenyl rings to which they are attached with dihedral angles O3—N1—C5—C6 and O3A—N1A—C5A—C4A being -1.9 (3) and 1.0 (3)°, respectively. The bond distances and angles in (I) agree well with the corresponding distances and angles reported in closely related structures (Adams & Morsi, 1976; Shibakami & Sekiya, 1995).

Experimental

2-Toluic acid (1.5 g, 1 mol) in a 100 ml two neck round bottom flask was gradually warmed on a water bath to 323 K. Dry thionyl chloride was added in excess slowly with stirring along with 2–3 drops of DMF as catalyst. The mixture was refluxed for about 50–60 minutes at 343 K. The excess of thionyl chloride was removed by repeated evaporation at reduced pressure. In a separate flask, 4-nitrophenol (1.5 g, 0.0065 mol) was dissolved in dry dichloromethane to which triethyl amine was added at room temperature to get transparent solution. The acid chloride was added into it drop wise with constant stirring at room temperature for 30 minutes under anhydrous condition and then poured into 20 ml of cold water. Excess of triethyl amine was removed by adding cold dilute HCl solution. The reaction was monitored by TLC using ethyl acetate: n-hexane (1:2). After the completion of reaction the oily product was allowed to settle down and the supernatant liquid was decanted. The product was stirred well with distilled water and extracted with ethyl acetate (3 x 40 ml), washed with 5% NaHCO3 solution and dried over anhydrous Na2SO4. After filtration the solution was concentrated to obtain the title compound which was recrystallized from n-hexane (Yield: 37 %; m.p. 336-344 K).

Refinement

H atoms were positioned geometrically and refined using a riding model with with C—H distances 0.95 and 0.98 Å for aromatic and methyl H-atoms, respectively, and displacement parameters, Uiso = 1.2 and 1.5 times Ueq of aromatic and methyl C-atoms, respectively. The methyl groups were allowed to rotate but not to tip. Due to the absence of anomalous scatterers, the absolute structure could not be determined which was set arbitrarily and Friedel pairs (1929) were merged.

Figures

Fig. 1.
Molecular structure of the independent molecule of the title compound with displacement parameters drawn at the 50% probability level.
Fig. 2.
Molecular structure of the other independent molecule of the title compound with displacement parameters drawn at the 50% probability level.

Crystal data

C14H11NO4F(000) = 1072
Mr = 257.24Dx = 1.421 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7991 reflections
a = 11.4748 (7) Åθ = 3.4–25.9°
b = 14.3608 (8) ŵ = 0.11 mm1
c = 14.5944 (9) ÅT = 173 K
V = 2405.0 (2) Å3Block, colourless
Z = 80.48 × 0.43 × 0.42 mm

Data collection

Stoe IPDS II two-circle diffractometer2233 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 25.6°, θmin = 3.4°
ω scansh = −13→11
8396 measured reflectionsk = −17→16
2536 independent reflectionsl = −17→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.081w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2536 reflectionsΔρmax = 0.19 e Å3
346 parametersΔρmin = −0.16 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: 0.0029 (6)

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 (Å2)

xyzUiso*/Ueq
O10.16002 (13)0.61145 (10)0.13451 (12)0.0313 (4)
O2−0.01252 (14)0.62719 (11)0.06228 (12)0.0350 (4)
O30.20623 (17)0.17957 (12)0.15433 (18)0.0603 (6)
O40.04224 (17)0.19478 (12)0.22316 (14)0.0484 (5)
N10.12619 (18)0.22748 (13)0.18336 (14)0.0330 (5)
C10.07279 (19)0.66283 (14)0.09413 (15)0.0252 (4)
C20.14470 (18)0.51564 (14)0.14478 (14)0.0257 (5)
C30.0478 (2)0.47887 (15)0.18780 (15)0.0279 (5)
H3−0.01340.51840.20810.033*
C40.04139 (19)0.38314 (15)0.20091 (15)0.0269 (5)
H4−0.02420.35590.23030.032*
C50.13290 (19)0.32834 (15)0.17014 (15)0.0262 (5)
C60.23122 (19)0.36492 (15)0.12783 (15)0.0276 (5)
H60.29290.32570.10800.033*
C70.23633 (19)0.46020 (15)0.11547 (15)0.0276 (5)
H70.30240.48760.08700.033*
C110.10142 (19)0.76401 (15)0.09643 (15)0.0257 (4)
C120.0246 (2)0.82974 (15)0.05781 (15)0.0289 (5)
C130.0559 (2)0.92345 (16)0.06402 (16)0.0356 (5)
H130.00540.96920.03890.043*
C140.1581 (3)0.95161 (16)0.10555 (17)0.0398 (6)
H140.17671.01600.10880.048*
C150.2334 (2)0.88691 (17)0.14233 (17)0.0389 (6)
H150.30430.90620.17010.047*
C160.2045 (2)0.79333 (16)0.13842 (16)0.0319 (5)
H160.25540.74850.16460.038*
C17−0.0882 (2)0.80479 (18)0.01122 (19)0.0397 (6)
H17A−0.14380.78150.05680.059*
H17B−0.07380.7564−0.03480.059*
H17C−0.12050.8602−0.01870.059*
O1A0.17914 (14)0.15192 (10)0.86948 (12)0.0341 (4)
O2A0.02001 (17)0.18630 (13)0.95339 (14)0.0502 (5)
O3A−0.00192 (18)−0.24935 (12)0.77876 (14)0.0505 (5)
O4A0.16863 (19)−0.28107 (13)0.83276 (17)0.0582 (6)
N1A0.09144 (18)−0.22567 (13)0.81235 (14)0.0338 (5)
C1A0.1056 (2)0.21228 (16)0.91421 (16)0.0323 (5)
C2A0.15008 (19)0.05831 (15)0.86021 (15)0.0275 (5)
C3A0.0438 (2)0.03078 (15)0.82310 (16)0.0290 (5)
H3A−0.01430.07550.80860.035*
C4A0.0245 (2)−0.06321 (15)0.80779 (14)0.0290 (5)
H4A−0.0475−0.08420.78310.035*
C5A0.1119 (2)−0.12599 (15)0.82913 (15)0.0273 (5)
C6A0.2179 (2)−0.09892 (16)0.86513 (16)0.0309 (5)
H6A0.2764−0.14360.87880.037*
C7A0.23671 (19)−0.00483 (17)0.88083 (16)0.0301 (5)
H7A0.30870.01590.90560.036*
C11A0.1498 (2)0.30931 (16)0.90502 (15)0.0314 (5)
C12A0.0759 (2)0.38603 (17)0.91703 (16)0.0358 (5)
C13A0.1220 (2)0.47552 (17)0.90166 (17)0.0393 (6)
H13A0.07270.52830.90760.047*
C14A0.2374 (3)0.48793 (17)0.87809 (18)0.0417 (6)
H14A0.26640.54900.86800.050*
C15A0.3114 (2)0.41263 (18)0.86902 (18)0.0418 (6)
H15A0.39130.42180.85450.050*
C16A0.2678 (2)0.32367 (16)0.88133 (16)0.0362 (5)
H16A0.31790.27160.87380.043*
C17A−0.0493 (2)0.3775 (2)0.9429 (2)0.0478 (7)
H17D−0.08910.33660.89920.072*
H17E−0.08580.43920.94180.072*
H17F−0.05550.35121.00460.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0282 (8)0.0198 (7)0.0458 (9)−0.0024 (6)−0.0051 (7)0.0052 (7)
O20.0326 (9)0.0235 (7)0.0490 (10)−0.0024 (7)−0.0090 (7)−0.0003 (7)
O30.0469 (11)0.0246 (9)0.1094 (18)0.0035 (9)0.0207 (12)−0.0050 (10)
O40.0533 (12)0.0290 (9)0.0628 (12)−0.0075 (9)0.0194 (10)0.0070 (8)
N10.0342 (11)0.0216 (9)0.0431 (11)−0.0006 (9)0.0008 (9)−0.0007 (8)
C10.0267 (11)0.0211 (10)0.0277 (10)0.0031 (9)0.0032 (9)0.0001 (9)
C20.0270 (11)0.0202 (10)0.0299 (11)−0.0019 (9)−0.0037 (9)0.0019 (8)
C30.0263 (11)0.0256 (11)0.0318 (12)0.0024 (9)0.0033 (9)−0.0006 (8)
C40.0267 (11)0.0235 (10)0.0305 (11)−0.0003 (9)0.0020 (9)0.0016 (8)
C50.0285 (11)0.0213 (10)0.0289 (10)−0.0010 (9)−0.0008 (9)0.0006 (8)
C60.0240 (10)0.0279 (11)0.0310 (11)0.0027 (9)0.0012 (9)−0.0005 (9)
C70.0229 (10)0.0285 (11)0.0313 (11)−0.0021 (9)0.0014 (9)0.0042 (9)
C110.0305 (11)0.0210 (10)0.0256 (10)−0.0011 (9)0.0058 (9)−0.0006 (8)
C120.0322 (12)0.0264 (11)0.0280 (11)0.0026 (9)0.0084 (9)0.0028 (8)
C130.0474 (14)0.0240 (11)0.0353 (13)0.0028 (11)0.0123 (11)0.0033 (9)
C140.0614 (17)0.0225 (11)0.0356 (12)−0.0074 (11)0.0124 (12)−0.0028 (10)
C150.0490 (15)0.0339 (13)0.0339 (12)−0.0134 (12)0.0030 (11)−0.0048 (10)
C160.0349 (12)0.0284 (11)0.0326 (12)−0.0034 (10)0.0008 (10)−0.0029 (9)
C170.0353 (13)0.0329 (13)0.0508 (15)0.0036 (11)−0.0013 (11)0.0137 (11)
O1A0.0339 (8)0.0227 (8)0.0458 (9)−0.0038 (7)0.0081 (8)−0.0041 (7)
O2A0.0481 (11)0.0414 (10)0.0612 (12)−0.0108 (9)0.0244 (10)−0.0146 (9)
O3A0.0573 (12)0.0319 (9)0.0624 (13)−0.0084 (9)−0.0172 (10)−0.0089 (8)
O4A0.0563 (12)0.0258 (9)0.0926 (16)0.0109 (9)−0.0109 (11)−0.0031 (10)
N1A0.0404 (11)0.0262 (10)0.0349 (11)−0.0008 (9)−0.0004 (9)−0.0034 (8)
C1A0.0328 (12)0.0315 (12)0.0326 (12)0.0001 (10)0.0041 (10)−0.0022 (10)
C2A0.0303 (11)0.0239 (10)0.0283 (10)−0.0027 (9)0.0064 (10)0.0003 (9)
C3A0.0275 (11)0.0262 (10)0.0332 (11)0.0046 (9)0.0006 (10)0.0028 (9)
C4A0.0290 (11)0.0294 (11)0.0285 (11)−0.0016 (10)−0.0027 (9)0.0014 (9)
C5A0.0318 (11)0.0234 (10)0.0267 (10)−0.0005 (9)0.0010 (9)−0.0014 (8)
C6A0.0290 (11)0.0276 (11)0.0361 (12)0.0047 (9)−0.0004 (10)0.0001 (10)
C7A0.0242 (10)0.0320 (11)0.0343 (12)−0.0011 (9)−0.0011 (9)−0.0017 (9)
C11A0.0400 (13)0.0285 (11)0.0257 (10)−0.0009 (10)−0.0022 (10)−0.0048 (9)
C12A0.0410 (13)0.0358 (13)0.0307 (12)0.0030 (11)−0.0060 (10)−0.0087 (10)
C13A0.0528 (15)0.0317 (12)0.0334 (12)0.0020 (11)−0.0113 (12)−0.0079 (10)
C14A0.0594 (16)0.0283 (13)0.0374 (13)−0.0031 (12)−0.0043 (12)−0.0024 (10)
C15A0.0449 (14)0.0360 (13)0.0446 (14)−0.0087 (12)0.0046 (12)−0.0023 (11)
C16A0.0451 (14)0.0268 (12)0.0366 (13)−0.0042 (11)0.0013 (11)−0.0005 (9)
C17A0.0438 (15)0.0465 (15)0.0532 (16)0.0061 (13)−0.0041 (13)−0.0124 (12)

Geometric parameters (Å, °)

O1—C11.376 (3)O1A—C1A1.375 (3)
O1—C21.395 (2)O1A—C2A1.392 (3)
O2—C11.199 (3)O2A—C1A1.196 (3)
O3—N11.223 (3)O3A—N1A1.226 (3)
O4—N11.219 (3)O4A—N1A1.227 (3)
N1—C51.463 (3)N1A—C5A1.471 (3)
C1—C111.490 (3)C1A—C11A1.489 (3)
C2—C31.382 (3)C2A—C7A1.379 (3)
C2—C71.387 (3)C2A—C3A1.392 (3)
C3—C41.390 (3)C3A—C4A1.386 (3)
C3—H30.9500C3A—H3A0.9500
C4—C51.387 (3)C4A—C5A1.384 (3)
C4—H40.9500C4A—H4A0.9500
C5—C61.389 (3)C5A—C6A1.381 (3)
C6—C71.381 (3)C6A—C7A1.387 (3)
C6—H60.9500C6A—H6A0.9500
C7—H70.9500C7A—H7A0.9500
C11—C161.397 (3)C11A—C12A1.401 (3)
C11—C121.409 (3)C11A—C16A1.412 (4)
C12—C131.396 (3)C12A—C13A1.408 (4)
C12—C171.505 (3)C12A—C17A1.491 (4)
C13—C141.381 (4)C13A—C14A1.380 (4)
C13—H130.9500C13A—H13A0.9500
C14—C151.377 (4)C14A—C15A1.381 (4)
C14—H140.9500C14A—H14A0.9500
C15—C161.385 (3)C15A—C16A1.384 (4)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C17—H17A0.9800C17A—H17D0.9800
C17—H17B0.9800C17A—H17E0.9800
C17—H17C0.9800C17A—H17F0.9800
C1—O1—C2118.90 (16)C1A—O1A—C2A120.55 (18)
O4—N1—O3122.80 (19)O3A—N1A—O4A123.2 (2)
O4—N1—C5119.06 (19)O3A—N1A—C5A118.4 (2)
O3—N1—C5118.1 (2)O4A—N1A—C5A118.4 (2)
O2—C1—O1122.09 (18)O2A—C1A—O1A122.3 (2)
O2—C1—C11127.2 (2)O2A—C1A—C11A127.9 (2)
O1—C1—C11110.67 (18)O1A—C1A—C11A109.76 (19)
C3—C2—C7122.06 (19)C7A—C2A—C3A122.0 (2)
C3—C2—O1121.81 (19)C7A—C2A—O1A116.19 (19)
C7—C2—O1115.96 (19)C3A—C2A—O1A121.5 (2)
C2—C3—C4118.9 (2)C4A—C3A—C2A118.7 (2)
C2—C3—H3120.5C4A—C3A—H3A120.7
C4—C3—H3120.5C2A—C3A—H3A120.7
C5—C4—C3118.5 (2)C5A—C4A—C3A118.8 (2)
C5—C4—H4120.8C5A—C4A—H4A120.6
C3—C4—H4120.8C3A—C4A—H4A120.6
C4—C5—C6123.0 (2)C6A—C5A—C4A122.7 (2)
C4—C5—N1118.6 (2)C6A—C5A—N1A118.5 (2)
C6—C5—N1118.4 (2)C4A—C5A—N1A118.7 (2)
C7—C6—C5117.8 (2)C5A—C6A—C7A118.3 (2)
C7—C6—H6121.1C5A—C6A—H6A120.8
C5—C6—H6121.1C7A—C6A—H6A120.8
C6—C7—C2119.8 (2)C2A—C7A—C6A119.5 (2)
C6—C7—H7120.1C2A—C7A—H7A120.3
C2—C7—H7120.1C6A—C7A—H7A120.3
C16—C11—C12120.2 (2)C12A—C11A—C16A119.7 (2)
C16—C11—C1119.4 (2)C12A—C11A—C1A121.2 (2)
C12—C11—C1120.4 (2)C16A—C11A—C1A119.0 (2)
C13—C12—C11117.3 (2)C11A—C12A—C13A118.1 (2)
C13—C12—C17118.7 (2)C11A—C12A—C17A123.4 (2)
C11—C12—C17124.0 (2)C13A—C12A—C17A118.5 (2)
C14—C13—C12122.0 (2)C14A—C13A—C12A121.2 (2)
C14—C13—H13119.0C14A—C13A—H13A119.4
C12—C13—H13119.0C12A—C13A—H13A119.4
C15—C14—C13120.4 (2)C13A—C14A—C15A120.8 (2)
C15—C14—H14119.8C13A—C14A—H14A119.6
C13—C14—H14119.8C15A—C14A—H14A119.6
C14—C15—C16119.2 (2)C14A—C15A—C16A119.2 (2)
C14—C15—H15120.4C14A—C15A—H15A120.4
C16—C15—H15120.4C16A—C15A—H15A120.4
C15—C16—C11120.9 (2)C15A—C16A—C11A120.9 (2)
C15—C16—H16119.6C15A—C16A—H16A119.6
C11—C16—H16119.6C11A—C16A—H16A119.6
C12—C17—H17A109.5C12A—C17A—H17D109.5
C12—C17—H17B109.5C12A—C17A—H17E109.5
H17A—C17—H17B109.5H17D—C17A—H17E109.5
C12—C17—H17C109.5C12A—C17A—H17F109.5
H17A—C17—H17C109.5H17D—C17A—H17F109.5
H17B—C17—H17C109.5H17E—C17A—H17F109.5
C2—O1—C1—O2−4.9 (3)C2A—O1A—C1A—O2A6.6 (4)
C2—O1—C1—C11175.37 (18)C2A—O1A—C1A—C11A−173.3 (2)
C1—O1—C2—C3−53.7 (3)C1A—O1A—C2A—C7A−133.2 (2)
C1—O1—C2—C7130.9 (2)C1A—O1A—C2A—C3A53.3 (3)
C7—C2—C3—C4−0.9 (3)C7A—C2A—C3A—C4A0.9 (3)
O1—C2—C3—C4−176.0 (2)O1A—C2A—C3A—C4A174.1 (2)
C2—C3—C4—C50.0 (3)C2A—C3A—C4A—C5A−0.6 (3)
C3—C4—C5—C60.8 (3)C3A—C4A—C5A—C6A0.0 (3)
C3—C4—C5—N1−179.7 (2)C3A—C4A—C5A—N1A−179.7 (2)
O4—N1—C5—C4−2.0 (3)O3A—N1A—C5A—C6A−178.6 (2)
O3—N1—C5—C4178.5 (2)O4A—N1A—C5A—C6A1.4 (3)
O4—N1—C5—C6177.5 (2)O3A—N1A—C5A—C4A1.0 (3)
O3—N1—C5—C6−1.9 (3)O4A—N1A—C5A—C4A−178.9 (2)
C4—C5—C6—C7−0.7 (3)C4A—C5A—C6A—C7A0.3 (3)
N1—C5—C6—C7179.8 (2)N1A—C5A—C6A—C7A180.0 (2)
C5—C6—C7—C2−0.2 (3)C3A—C2A—C7A—C6A−0.6 (4)
C3—C2—C7—C61.0 (3)O1A—C2A—C7A—C6A−174.1 (2)
O1—C2—C7—C6176.4 (2)C5A—C6A—C7A—C2A−0.1 (4)
O2—C1—C11—C16178.7 (2)O2A—C1A—C11A—C12A−20.9 (4)
O1—C1—C11—C16−1.6 (3)O1A—C1A—C11A—C12A159.0 (2)
O2—C1—C11—C12−0.4 (4)O2A—C1A—C11A—C16A160.8 (3)
O1—C1—C11—C12179.30 (19)O1A—C1A—C11A—C16A−19.3 (3)
C16—C11—C12—C13−0.3 (3)C16A—C11A—C12A—C13A2.2 (3)
C1—C11—C12—C13178.79 (19)C1A—C11A—C12A—C13A−176.1 (2)
C16—C11—C12—C17180.0 (2)C16A—C11A—C12A—C17A−179.4 (2)
C1—C11—C12—C17−0.9 (3)C1A—C11A—C12A—C17A2.3 (4)
C11—C12—C13—C140.4 (3)C11A—C12A—C13A—C14A−1.9 (4)
C17—C12—C13—C14−179.8 (2)C17A—C12A—C13A—C14A179.6 (2)
C12—C13—C14—C150.2 (4)C12A—C13A—C14A—C15A−0.1 (4)
C13—C14—C15—C16−1.0 (4)C13A—C14A—C15A—C16A1.8 (4)
C14—C15—C16—C111.1 (4)C14A—C15A—C16A—C11A−1.5 (4)
C12—C11—C16—C15−0.4 (3)C12A—C11A—C16A—C15A−0.5 (4)
C1—C11—C16—C15−179.6 (2)C1A—C11A—C16A—C15A177.8 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2221).

References

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