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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1746.
Published online 2009 July 4. doi:  10.1107/S1600536809024593
PMCID: PMC2977274

(E)-4-(2,5-Dimethoxy­benzyl­idene)-2-phenyl-1,3-oxazol-5(4H)-one

Abstract

The central aza­lactone ring in the title compound, C18H15NO4, is planar (r.m.s. deviation 0.05, 0.12 Å) in both independent mol­ecules comprising the asymmetric unit. The benzyl­idene substituent is coplanar with this ring [dihedral angle between the planes = 1.8 (1)° in the first mol­ecule and 2.8 (1)° in the second], as is the phenyl substitutent [dihedral angle between rings = 4.6 (1) and 9.7 (1)°, respectively].

Related literature

For the synthesis of this aza­lactone (which is used in the synthesis of other bioactive compounds), see: Bansal & Jain (1968 [triangle]); Gulland & Virden (1928 [triangle]); Hoseini & Jabar (2003 [triangle]); Khosropour et al. (2008 [triangle]); Neuberger (1948 [triangle]); Radadia et al. (2006 [triangle]); Solankee et al. (2004 [triangle]); Yakovlev (1950 [triangle]).

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Object name is e-65-o1746-scheme1.jpg

Experimental

Crystal data

  • C18H15NO4
  • M r = 309.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1746-efi1.jpg
  • a = 7.3893 (2) Å
  • b = 10.6747 (3) Å
  • c = 19.9788 (5) Å
  • α = 92.408 (2)°
  • β = 89.780 (2)°
  • γ = 109.589 (2)°
  • V = 1483.29 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 140 K
  • 0.35 × 0.25 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 12194 measured reflections
  • 6674 independent reflections
  • 4460 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.124
  • S = 1.02
  • 6674 reflections
  • 419 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024593/tk2485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024593/tk2485Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Anhydrous sodium acetate (0.23 g, 0.0032 mol) was added to an acetic anhydride (0.12 ml, 0.0028 mol) solution of 2,5-dimethoxybenzaldehyde (1 g, 0.0032 mol) and hippuric acid (0.68 g, 0.0038 mol). The mixture was heated to 353 K for 2 h. The mixture was cooled and ethanol (10 ml) added. The crude azalactone was collected and washed with hot water. Recrystallization from acetone/water (1/1) afforded the pure azalactone as yellow-crystals crystals in 70% yield; m.p. 448 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation with U(H) fixed at 1.2–1.5Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C18H15NO4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H15NO4Z = 4
Mr = 309.31F(000) = 648
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3893 (2) ÅCell parameters from 2608 reflections
b = 10.6747 (3) Åθ = 2.9–27.5°
c = 19.9788 (5) ŵ = 0.10 mm1
α = 92.408 (2)°T = 140 K
β = 89.780 (2)°Plate, yellow-orange
γ = 109.589 (2)°0.35 × 0.25 × 0.05 mm
V = 1483.29 (7) Å3

Data collection

Bruker SMART APEX diffractometer4460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 27.5°, θmin = 1.0°
ω scansh = −9→9
12194 measured reflectionsk = −13→13
6674 independent reflectionsl = −25→24

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0549P)2 + 0.1872P] where P = (Fo2 + 2Fc2)/3
6674 reflections(Δ/σ)max = 0.001
419 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.21 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.33728 (19)0.62721 (13)0.40379 (6)0.0310 (3)
O20.6638 (2)1.10751 (14)0.28431 (7)0.0382 (4)
O30.86578 (18)1.00629 (12)0.62162 (6)0.0263 (3)
O40.6850 (2)0.78813 (14)0.62357 (7)0.0377 (4)
O50.3182 (2)0.87366 (13)−0.04754 (6)0.0305 (3)
O60.4181 (2)0.43230 (14)−0.17481 (7)0.0365 (4)
O70.10590 (18)0.44231 (12)0.16427 (6)0.0256 (3)
O80.1178 (2)0.65709 (13)0.16969 (6)0.0333 (3)
N10.8113 (2)1.05526 (14)0.51618 (7)0.0226 (3)
N20.1863 (2)0.41791 (15)0.05614 (7)0.0231 (3)
C10.4144 (3)0.74516 (19)0.37318 (9)0.0254 (4)
C20.3736 (3)0.7636 (2)0.30708 (9)0.0293 (4)
H20.28710.69220.28100.035*
C30.4585 (3)0.8855 (2)0.27937 (9)0.0319 (5)
H30.42950.89740.23430.038*
C40.5857 (3)0.99073 (19)0.31638 (9)0.0286 (4)
C50.6260 (3)0.97409 (19)0.38221 (9)0.0247 (4)
H50.71201.04660.40780.030*
C60.5414 (3)0.85146 (18)0.41178 (9)0.0223 (4)
C70.2236 (3)0.5148 (2)0.36339 (11)0.0389 (5)
H7A0.18960.43480.38960.058*
H7B0.29710.50310.32410.058*
H7C0.10610.52940.34870.058*
C80.7886 (3)1.2170 (2)0.32279 (10)0.0376 (5)
H8A0.82951.29580.29560.056*
H8B0.90151.19590.33700.056*
H8C0.72091.23490.36240.056*
C90.5850 (3)0.83215 (18)0.48039 (9)0.0229 (4)
H90.52300.74570.49630.028*
C100.7022 (3)0.92109 (18)0.52466 (9)0.0227 (4)
C110.7383 (3)0.88791 (19)0.59291 (9)0.0257 (4)
C120.8990 (3)1.09834 (18)0.57233 (8)0.0218 (4)
C131.0307 (3)1.23148 (18)0.58871 (9)0.0230 (4)
C141.0778 (3)1.32452 (19)0.53919 (10)0.0302 (4)
H141.01841.30210.49620.036*
C151.2108 (3)1.4497 (2)0.55242 (11)0.0357 (5)
H151.24361.51300.51850.043*
C161.2964 (3)1.4825 (2)0.61529 (11)0.0346 (5)
H161.38981.56780.62410.042*
C171.2466 (3)1.3922 (2)0.66500 (10)0.0330 (5)
H171.30291.41640.70840.040*
C181.1146 (3)1.26620 (19)0.65212 (9)0.0279 (4)
H181.08151.20370.68640.033*
C190.3386 (3)0.76448 (19)−0.08112 (9)0.0257 (4)
C200.3947 (3)0.7645 (2)−0.14757 (9)0.0291 (4)
H200.41770.8421−0.17250.035*
C210.4172 (3)0.6517 (2)−0.17748 (9)0.0306 (5)
H210.45550.6521−0.22290.037*
C220.3841 (3)0.5380 (2)−0.14169 (9)0.0281 (4)
C230.3232 (3)0.53509 (19)−0.07638 (9)0.0257 (4)
H230.29730.4559−0.05260.031*
C240.2991 (3)0.64866 (18)−0.04463 (9)0.0235 (4)
C250.3610 (3)0.99354 (19)−0.08297 (10)0.0335 (5)
H25A0.34841.0648−0.05270.050*
H25B0.27130.9792−0.12080.050*
H25C0.49281.0189−0.09960.050*
C260.3406 (3)0.3058 (2)−0.14667 (11)0.0375 (5)
H26A0.35960.2376−0.17760.056*
H26B0.20300.2861−0.13900.056*
H26C0.40590.3063−0.10400.056*
C270.2365 (3)0.64931 (19)0.02420 (9)0.0250 (4)
H270.22800.73130.04160.030*
C280.1887 (3)0.54878 (18)0.06689 (9)0.0229 (4)
C290.1353 (3)0.56526 (19)0.13700 (9)0.0255 (4)
C300.1396 (3)0.36291 (18)0.11257 (8)0.0224 (4)
C310.1247 (3)0.22752 (18)0.12781 (9)0.0235 (4)
C320.1394 (3)0.14044 (19)0.07566 (9)0.0272 (4)
H320.15340.16840.03080.033*
C330.1334 (3)0.0136 (2)0.08943 (10)0.0312 (5)
H330.1422−0.04640.05410.037*
C340.1146 (3)−0.0264 (2)0.15501 (10)0.0325 (5)
H340.1108−0.11370.16430.039*
C350.1013 (3)0.0595 (2)0.20680 (10)0.0340 (5)
H350.08940.03160.25160.041*
C360.1054 (3)0.1865 (2)0.19328 (10)0.0301 (4)
H36B0.09500.24560.22880.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0311 (8)0.0234 (7)0.0329 (7)0.0022 (6)−0.0059 (6)−0.0049 (6)
O20.0464 (9)0.0380 (9)0.0277 (7)0.0101 (7)−0.0024 (6)0.0087 (6)
O30.0310 (7)0.0217 (7)0.0221 (6)0.0032 (6)−0.0041 (5)0.0010 (5)
O40.0487 (9)0.0254 (8)0.0309 (8)0.0012 (7)−0.0068 (7)0.0067 (6)
O50.0376 (8)0.0238 (7)0.0299 (7)0.0094 (6)0.0004 (6)0.0072 (6)
O60.0440 (9)0.0334 (8)0.0300 (8)0.0108 (7)0.0050 (6)−0.0014 (6)
O70.0309 (7)0.0246 (7)0.0213 (6)0.0094 (6)−0.0002 (5)0.0011 (5)
O80.0471 (9)0.0265 (8)0.0269 (7)0.0135 (7)−0.0043 (6)−0.0043 (6)
N10.0245 (8)0.0190 (8)0.0235 (8)0.0061 (7)0.0005 (6)−0.0001 (6)
N20.0233 (8)0.0229 (8)0.0229 (8)0.0072 (7)−0.0025 (6)0.0021 (6)
C10.0245 (10)0.0255 (10)0.0271 (10)0.0099 (9)0.0007 (8)−0.0029 (8)
C20.0278 (10)0.0351 (12)0.0251 (10)0.0120 (9)−0.0052 (8)−0.0089 (8)
C30.0358 (12)0.0434 (13)0.0196 (9)0.0178 (10)−0.0037 (8)−0.0014 (9)
C40.0335 (11)0.0301 (11)0.0252 (10)0.0144 (9)0.0013 (8)0.0039 (8)
C50.0248 (10)0.0258 (10)0.0234 (9)0.0088 (8)−0.0012 (7)−0.0026 (8)
C60.0208 (9)0.0247 (10)0.0226 (9)0.0096 (8)0.0009 (7)−0.0010 (7)
C70.0361 (12)0.0265 (11)0.0477 (13)0.0036 (10)−0.0088 (10)−0.0112 (10)
C80.0441 (13)0.0316 (12)0.0355 (12)0.0099 (11)0.0034 (10)0.0078 (9)
C90.0232 (10)0.0203 (10)0.0248 (9)0.0067 (8)0.0022 (7)−0.0001 (7)
C100.0241 (10)0.0216 (10)0.0228 (9)0.0083 (8)0.0016 (7)−0.0001 (7)
C110.0280 (10)0.0224 (10)0.0249 (9)0.0061 (9)−0.0032 (8)−0.0004 (8)
C120.0228 (9)0.0223 (10)0.0211 (9)0.0088 (8)0.0018 (7)0.0012 (7)
C130.0207 (9)0.0212 (10)0.0264 (9)0.0063 (8)−0.0003 (7)−0.0031 (7)
C140.0334 (11)0.0255 (11)0.0291 (10)0.0066 (9)−0.0017 (8)−0.0012 (8)
C150.0388 (12)0.0239 (11)0.0402 (12)0.0045 (10)0.0039 (9)0.0040 (9)
C160.0290 (11)0.0227 (11)0.0485 (13)0.0049 (9)−0.0021 (9)−0.0068 (9)
C170.0305 (11)0.0292 (11)0.0373 (11)0.0087 (9)−0.0109 (9)−0.0088 (9)
C180.0281 (11)0.0249 (10)0.0302 (10)0.0086 (9)−0.0028 (8)−0.0009 (8)
C190.0240 (10)0.0255 (10)0.0259 (10)0.0059 (8)−0.0061 (8)0.0032 (8)
C200.0271 (10)0.0282 (11)0.0268 (10)0.0017 (9)−0.0048 (8)0.0077 (8)
C210.0268 (11)0.0377 (12)0.0211 (10)0.0022 (9)−0.0015 (8)0.0029 (8)
C220.0243 (10)0.0315 (11)0.0256 (10)0.0056 (9)−0.0036 (8)−0.0021 (8)
C230.0226 (10)0.0253 (10)0.0261 (10)0.0035 (8)−0.0030 (7)0.0032 (8)
C240.0192 (9)0.0251 (10)0.0242 (9)0.0043 (8)−0.0035 (7)0.0039 (8)
C250.0352 (12)0.0254 (11)0.0399 (12)0.0088 (9)−0.0002 (9)0.0107 (9)
C260.0383 (12)0.0307 (12)0.0417 (12)0.0098 (10)0.0010 (10)−0.0030 (9)
C270.0267 (10)0.0231 (10)0.0252 (9)0.0084 (8)−0.0057 (8)0.0011 (8)
C280.0236 (10)0.0234 (10)0.0210 (9)0.0071 (8)−0.0032 (7)0.0000 (7)
C290.0262 (10)0.0236 (10)0.0245 (9)0.0053 (8)−0.0052 (7)0.0011 (8)
C300.0204 (9)0.0258 (10)0.0214 (9)0.0085 (8)−0.0024 (7)−0.0014 (7)
C310.0202 (9)0.0236 (10)0.0263 (9)0.0066 (8)−0.0011 (7)0.0034 (8)
C320.0270 (10)0.0290 (11)0.0264 (10)0.0102 (9)−0.0018 (8)0.0012 (8)
C330.0288 (11)0.0288 (11)0.0367 (11)0.0111 (9)−0.0057 (8)−0.0045 (9)
C340.0303 (11)0.0240 (11)0.0424 (12)0.0075 (9)−0.0049 (9)0.0065 (9)
C350.0385 (12)0.0321 (12)0.0299 (11)0.0088 (10)0.0007 (9)0.0098 (9)
C360.0339 (11)0.0284 (11)0.0271 (10)0.0090 (9)0.0041 (8)0.0049 (8)

Geometric parameters (Å, °)

O1—C11.366 (2)C14—C151.383 (3)
O1—C71.430 (2)C14—H140.9500
O2—C41.371 (2)C15—C161.386 (3)
O2—C81.419 (2)C15—H150.9500
O3—C121.383 (2)C16—C171.375 (3)
O3—C111.399 (2)C16—H160.9500
O4—C111.199 (2)C17—C181.386 (3)
O5—C191.372 (2)C17—H170.9500
O5—C251.429 (2)C18—H180.9500
O6—C221.378 (2)C19—C201.389 (3)
O6—C261.418 (2)C19—C241.406 (3)
O7—C301.383 (2)C20—C211.381 (3)
O7—C291.391 (2)C20—H200.9500
O8—C291.198 (2)C21—C221.384 (3)
N1—C121.286 (2)C21—H210.9500
N1—C101.405 (2)C22—C231.377 (3)
N2—C301.285 (2)C23—C241.408 (3)
N2—C281.399 (2)C23—H230.9500
C1—C21.392 (3)C24—C271.450 (2)
C1—C61.408 (2)C25—H25A0.9800
C2—C31.380 (3)C25—H25B0.9800
C2—H20.9500C25—H25C0.9800
C3—C41.385 (3)C26—H26A0.9800
C3—H30.9500C26—H26B0.9800
C4—C51.382 (2)C26—H26C0.9800
C5—C61.402 (3)C27—C281.351 (2)
C5—H50.9500C27—H270.9500
C6—C91.448 (2)C28—C291.473 (2)
C7—H7A0.9800C30—C311.457 (2)
C7—H7B0.9800C31—C361.389 (3)
C7—H7C0.9800C31—C321.395 (2)
C8—H8A0.9800C32—C331.380 (3)
C8—H8B0.9800C32—H320.9500
C8—H8C0.9800C33—C341.387 (3)
C9—C101.348 (2)C33—H330.9500
C9—H90.9500C34—C351.379 (3)
C10—C111.471 (2)C34—H340.9500
C12—C131.453 (3)C35—C361.384 (3)
C13—C141.391 (3)C35—H350.9500
C13—C181.393 (2)C36—H36B0.9500
C1—O1—C7117.44 (15)C18—C17—H17119.9
C4—O2—C8116.75 (15)C17—C18—C13119.78 (18)
C12—O3—C11105.55 (13)C17—C18—H18120.1
C19—O5—C25117.65 (15)C13—C18—H18120.1
C22—O6—C26117.31 (15)O5—C19—C20123.37 (17)
C30—O7—C29105.28 (13)O5—C19—C24116.41 (16)
C12—N1—C10105.88 (15)C20—C19—C24120.22 (17)
C30—N2—C28105.50 (14)C21—C20—C19120.04 (18)
O1—C1—C2123.37 (17)C21—C20—H20120.0
O1—C1—C6116.80 (16)C19—C20—H20120.0
C2—C1—C6119.82 (18)C20—C21—C22120.46 (18)
C3—C2—C1120.05 (18)C20—C21—H21119.8
C3—C2—H2120.0C22—C21—H21119.8
C1—C2—H2120.0O6—C22—C23123.41 (18)
C2—C3—C4120.91 (18)O6—C22—C21116.33 (17)
C2—C3—H3119.5C23—C22—C21120.26 (18)
C4—C3—H3119.5C22—C23—C24120.47 (18)
O2—C4—C5123.80 (18)C22—C23—H23119.8
O2—C4—C3116.59 (17)C24—C23—H23119.8
C5—C4—C3119.61 (19)C19—C24—C23118.50 (17)
C4—C5—C6120.76 (17)C19—C24—C27119.58 (16)
C4—C5—H5119.6C23—C24—C27121.92 (17)
C6—C5—H5119.6O5—C25—H25A109.5
C5—C6—C1118.84 (16)O5—C25—H25B109.5
C5—C6—C9121.28 (16)H25A—C25—H25B109.5
C1—C6—C9119.87 (17)O5—C25—H25C109.5
O1—C7—H7A109.5H25A—C25—H25C109.5
O1—C7—H7B109.5H25B—C25—H25C109.5
H7A—C7—H7B109.5O6—C26—H26A109.5
O1—C7—H7C109.5O6—C26—H26B109.5
H7A—C7—H7C109.5H26A—C26—H26B109.5
H7B—C7—H7C109.5O6—C26—H26C109.5
O2—C8—H8A109.5H26A—C26—H26C109.5
O2—C8—H8B109.5H26B—C26—H26C109.5
H8A—C8—H8B109.5C28—C27—C24128.61 (17)
O2—C8—H8C109.5C28—C27—H27115.7
H8A—C8—H8C109.5C24—C27—H27115.7
H8B—C8—H8C109.5C27—C28—N2129.08 (16)
C10—C9—C6128.36 (18)C27—C28—C29122.81 (16)
C10—C9—H9115.8N2—C28—C29108.07 (15)
C6—C9—H9115.8O8—C29—O7121.70 (17)
C9—C10—N1128.96 (17)O8—C29—C28133.35 (18)
C9—C10—C11123.11 (17)O7—C29—C28104.95 (15)
N1—C10—C11107.92 (15)N2—C30—O7116.19 (16)
O4—C11—O3121.15 (16)N2—C30—C31126.59 (16)
O4—C11—C10134.02 (18)O7—C30—C31117.19 (15)
O3—C11—C10104.83 (15)C36—C31—C32119.94 (17)
N1—C12—O3115.80 (16)C36—C31—C30121.12 (17)
N1—C12—C13127.03 (16)C32—C31—C30118.87 (16)
O3—C12—C13117.16 (15)C33—C32—C31119.74 (18)
C14—C13—C18119.62 (17)C33—C32—H32120.1
C14—C13—C12118.97 (16)C31—C32—H32120.1
C18—C13—C12121.38 (17)C32—C33—C34119.89 (19)
C15—C14—C13120.12 (18)C32—C33—H33120.1
C15—C14—H14119.9C34—C33—H33120.1
C13—C14—H14119.9C35—C34—C33120.63 (19)
C14—C15—C16119.8 (2)C35—C34—H34119.7
C14—C15—H15120.1C33—C34—H34119.7
C16—C15—H15120.1C34—C35—C36119.79 (19)
C17—C16—C15120.32 (19)C34—C35—H35120.1
C17—C16—H16119.8C36—C35—H35120.1
C15—C16—H16119.8C35—C36—C31120.01 (18)
C16—C17—C18120.28 (18)C35—C36—H36B120.0
C16—C17—H17119.9C31—C36—H36B120.0
C7—O1—C1—C26.1 (3)C25—O5—C19—C20−1.3 (3)
C7—O1—C1—C6−173.82 (16)C25—O5—C19—C24178.80 (16)
O1—C1—C2—C3−179.40 (17)O5—C19—C20—C21178.28 (17)
C6—C1—C2—C30.5 (3)C24—C19—C20—C21−1.8 (3)
C1—C2—C3—C40.3 (3)C19—C20—C21—C220.0 (3)
C8—O2—C4—C5−1.9 (3)C26—O6—C22—C2316.6 (3)
C8—O2—C4—C3177.74 (17)C26—O6—C22—C21−164.31 (17)
C2—C3—C4—O2179.50 (16)C20—C21—C22—O6−177.32 (17)
C2—C3—C4—C5−0.9 (3)C20—C21—C22—C231.8 (3)
O2—C4—C5—C6−179.69 (17)O6—C22—C23—C24177.30 (17)
C3—C4—C5—C60.7 (3)C21—C22—C23—C24−1.8 (3)
C4—C5—C6—C10.0 (3)O5—C19—C24—C23−178.26 (16)
C4—C5—C6—C9178.98 (17)C20—C19—C24—C231.9 (3)
O1—C1—C6—C5179.25 (15)O5—C19—C24—C271.3 (2)
C2—C1—C6—C5−0.6 (3)C20—C19—C24—C27−178.60 (16)
O1—C1—C6—C90.3 (2)C22—C23—C24—C190.0 (3)
C2—C1—C6—C9−179.61 (17)C22—C23—C24—C27−179.57 (17)
C5—C6—C9—C100.9 (3)C19—C24—C27—C28178.73 (18)
C1—C6—C9—C10179.88 (18)C23—C24—C27—C28−1.7 (3)
C6—C9—C10—N10.4 (3)C24—C27—C28—N2−0.2 (3)
C6—C9—C10—C11−178.41 (17)C24—C27—C28—C29177.19 (17)
C12—N1—C10—C9179.93 (18)C30—N2—C28—C27177.07 (19)
C12—N1—C10—C11−1.09 (19)C30—N2—C28—C29−0.60 (19)
C12—O3—C11—O4178.61 (18)C30—O7—C29—O8−179.66 (17)
C12—O3—C11—C10−0.44 (18)C30—O7—C29—C28−0.32 (17)
C9—C10—C11—O41.1 (3)C27—C28—C29—O82.0 (3)
N1—C10—C11—O4−177.9 (2)N2—C28—C29—O8179.8 (2)
C9—C10—C11—O3180.00 (16)C27—C28—C29—O7−177.27 (16)
N1—C10—C11—O30.94 (19)N2—C28—C29—O70.58 (18)
C10—N1—C12—O30.9 (2)C28—N2—C30—O70.4 (2)
C10—N1—C12—C13179.58 (16)C28—N2—C30—C31−177.57 (17)
C11—O3—C12—N1−0.3 (2)C29—O7—C30—N2−0.1 (2)
C11—O3—C12—C13−179.11 (15)C29—O7—C30—C31178.13 (15)
N1—C12—C13—C14−2.9 (3)N2—C30—C31—C36168.82 (18)
O3—C12—C13—C14175.82 (16)O7—C30—C31—C36−9.2 (3)
N1—C12—C13—C18179.07 (18)N2—C30—C31—C32−8.1 (3)
O3—C12—C13—C18−2.2 (2)O7—C30—C31—C32173.89 (15)
C18—C13—C14—C151.6 (3)C36—C31—C32—C330.4 (3)
C12—C13—C14—C15−176.45 (17)C30—C31—C32—C33177.37 (17)
C13—C14—C15—C16−0.4 (3)C31—C32—C33—C34−0.6 (3)
C14—C15—C16—C17−1.4 (3)C32—C33—C34—C350.1 (3)
C15—C16—C17—C181.9 (3)C33—C34—C35—C360.5 (3)
C16—C17—C18—C13−0.7 (3)C34—C35—C36—C31−0.6 (3)
C14—C13—C18—C17−1.1 (3)C32—C31—C36—C350.2 (3)
C12—C13—C18—C17176.95 (17)C30—C31—C36—C35−176.72 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2485).

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