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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o126.
Published online 2009 December 12. doi:  10.1107/S1600536809052696
PMCID: PMC2980270

Ethyl 2-{4-[(1,5-dibenzyl-2,4-dioxo-2,3,4,5-tetra­hydro-1H-1,5-benzo­diazepin-3-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

Abstract

The reaction of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione with ethyl azido­acetate in the presence of copper sulfate pentahydrate and sodium ascorbate leads to the formation of the title regioisomer, C30H29N5O4, which features a phenyl­ene ring fused with a seven-membered diazepinyl ring. The latter ring adopts a boat conformation (with the methyl­triazolylacetate-bearing C atom as the prow and the fused-ring C atoms as the stern). The benzyl groups connected to the diazepinyl ring jprotrude from the sides; the methyl­triazolylacetate substituent occupies an axial position.

Related literature

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006 [triangle]). For the crystal structure of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Jabli et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o126-scheme1.jpg

Experimental

Crystal data

  • C30H29N5O4
  • M r = 523.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o126-efi1.jpg
  • a = 14.2015 (5) Å
  • b = 10.9337 (4) Å
  • c = 17.9368 (6) Å
  • β = 95.699 (2)°
  • V = 2771.37 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 243 K
  • 0.30 × 0.22 × 0.08 mm

Data collection

  • Bruker APEXII diffractometer
  • 29097 measured reflections
  • 6377 independent reflections
  • 2690 reflections with I > 2σ(I)
  • R int = 0.079
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.174
  • S = 1.00
  • 6377 reflections
  • 352 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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/S1600536809052696/sj2708sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052696/sj2708Isup2.hkl

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

Acknowledgments

We thank Université Mohammed V-Agdal, University Sidi Mohammed Ben Abdallah and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution 1,5-dibenzyl-1,5-benzodiazepine-2,4-dione (1 mmol) t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and ethyl azidoacetate (5 mmol). Stirring was continued for 8 h. The solution was diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 x 20 ml). The extracts were washed with brine and dried over sodium sulfate. The compound was recrystallized from ether to give colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.94 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The carbon-carbon distance in the ethyl end of the molecule was tightly restrained to 1.540±0.005 Å. Attempts to model this unit as being disordered over two sites required a large number of restraints.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C30H29N5O4 at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C30H29N5O4F(000) = 1104
Mr = 523.58Dx = 1.255 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2371 reflections
a = 14.2015 (5) Åθ = 2.2–18.1°
b = 10.9337 (4) ŵ = 0.09 mm1
c = 17.9368 (6) ÅT = 243 K
β = 95.699 (2)°Block, colorless
V = 2771.37 (17) Å30.30 × 0.22 × 0.08 mm
Z = 4

Data collection

Bruker APEXII diffractometer2690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
graphiteθmax = 27.5°, θmin = 1.4°
[var phi] and ω scansh = −15→18
29097 measured reflectionsk = −11→14
6377 independent reflectionsl = −23→23

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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0719P)2 + 0.0345P] where P = (Fo2 + 2Fc2)/3
6377 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 0.48 e Å3
1 restraintΔρmin = −0.22 e Å3

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

xyzUiso*/Ueq
O10.37697 (14)1.09779 (17)0.39010 (11)0.0567 (6)
O20.11543 (14)1.08866 (18)0.41866 (11)0.0600 (6)
O30.70046 (15)0.63752 (18)0.54560 (12)0.0665 (6)
O40.60809 (16)0.7150 (2)0.44777 (13)0.0844 (8)
N10.31956 (15)1.0200 (2)0.27730 (12)0.0482 (6)
N20.11754 (15)1.0312 (2)0.29647 (12)0.0483 (6)
N30.31787 (17)0.7234 (2)0.46224 (13)0.0557 (7)
N40.38706 (18)0.6481 (2)0.48645 (13)0.0576 (7)
N50.45203 (16)0.7143 (2)0.52910 (12)0.0484 (6)
C10.2513 (2)0.9476 (3)0.23315 (14)0.0471 (7)
C20.2827 (3)0.8723 (3)0.17821 (18)0.0732 (10)
H20.34780.86580.17350.088*
C30.2187 (3)0.8067 (4)0.1304 (2)0.0931 (13)
H30.24040.75520.09380.112*
C40.1223 (3)0.8172 (3)0.13675 (19)0.0830 (11)
H40.07860.77530.10310.100*
C50.0908 (2)0.8889 (3)0.19218 (16)0.0630 (9)
H50.02560.89340.19710.076*
C60.1540 (2)0.9551 (2)0.24119 (14)0.0455 (7)
C70.38849 (19)1.0938 (3)0.23979 (16)0.0544 (8)
H7A0.38871.17680.26040.065*
H7B0.36581.09960.18650.065*
C80.49003 (19)1.0480 (2)0.24595 (15)0.0459 (7)
C90.5521 (2)1.1034 (3)0.20078 (16)0.0561 (8)
H90.52941.16430.16660.067*
C100.6470 (2)1.0702 (3)0.2054 (2)0.0703 (10)
H100.68751.10730.17370.084*
C110.6819 (2)0.9829 (3)0.25645 (19)0.0705 (9)
H110.74640.96180.26040.085*
C120.6217 (2)0.9267 (3)0.30160 (18)0.0628 (9)
H120.64510.86670.33620.075*
C130.5257 (2)0.9588 (3)0.29596 (16)0.0558 (8)
H130.48490.91940.32650.067*
C140.0279 (2)1.0971 (3)0.27638 (17)0.0630 (9)
H14A0.01491.14990.31830.076*
H14B−0.02371.03750.26880.076*
C150.0286 (2)1.1742 (3)0.20694 (15)0.0498 (7)
C16−0.0512 (2)1.1786 (3)0.15552 (17)0.0598 (8)
H16−0.10451.13140.16360.072*
C17−0.0530 (3)1.2522 (3)0.09205 (19)0.0702 (10)
H17−0.10711.25380.05740.084*
C180.0242 (3)1.3224 (3)0.08008 (19)0.0728 (10)
H180.02271.37200.03720.087*
C190.1046 (2)1.3204 (3)0.1311 (2)0.0711 (9)
H190.15721.36890.12310.085*
C200.1064 (2)1.2457 (3)0.19446 (18)0.0637 (9)
H200.16071.24380.22890.076*
C210.32027 (19)1.0305 (2)0.35331 (16)0.0449 (7)
C220.24439 (18)0.9589 (2)0.38906 (14)0.0408 (6)
H220.23730.87740.36520.049*
C230.15274 (19)1.0309 (2)0.37117 (16)0.0456 (7)
C240.27037 (19)0.9424 (2)0.47331 (14)0.0475 (7)
H24A0.29861.01810.49450.057*
H24B0.21290.92600.49770.057*
C250.33895 (19)0.8388 (2)0.48895 (14)0.0424 (7)
C260.4240 (2)0.8323 (2)0.53126 (15)0.0493 (7)
H260.45670.89690.55680.059*
C270.5400 (2)0.6571 (3)0.56053 (16)0.0526 (8)
H27A0.52940.56950.56740.063*
H27B0.55940.69270.60980.063*
C280.6185 (2)0.6746 (3)0.51023 (19)0.0557 (8)
C290.7809 (2)0.6436 (4)0.5009 (2)0.0954 (13)
H29A0.79790.72910.49280.114*
H29B0.76450.60520.45200.114*
C300.8613 (3)0.5788 (4)0.5417 (3)0.155 (2)
H30A0.91540.58190.51270.232*
H30B0.84410.49420.54930.232*
H30C0.87740.61770.58990.232*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0539 (13)0.0544 (12)0.0612 (13)−0.0108 (10)0.0030 (11)−0.0064 (10)
O20.0620 (14)0.0655 (13)0.0542 (13)0.0135 (11)0.0145 (11)−0.0095 (11)
O30.0555 (14)0.0591 (14)0.0836 (16)0.0036 (11)−0.0003 (13)0.0102 (11)
O40.0740 (17)0.120 (2)0.0600 (15)0.0123 (14)0.0093 (13)0.0211 (14)
N10.0452 (14)0.0583 (15)0.0424 (14)−0.0054 (12)0.0108 (12)0.0026 (11)
N20.0456 (14)0.0554 (14)0.0442 (14)0.0092 (11)0.0058 (11)0.0036 (11)
N30.0560 (16)0.0506 (15)0.0588 (16)0.0016 (13)−0.0017 (13)−0.0098 (12)
N40.0586 (17)0.0468 (14)0.0656 (17)−0.0035 (13)−0.0027 (14)−0.0102 (13)
N50.0538 (15)0.0400 (13)0.0500 (14)−0.0046 (12)−0.0013 (12)0.0011 (11)
C10.0504 (19)0.0582 (18)0.0341 (15)−0.0024 (15)0.0103 (14)−0.0017 (13)
C20.074 (2)0.092 (3)0.059 (2)−0.005 (2)0.0277 (19)−0.0179 (19)
C30.106 (3)0.117 (3)0.060 (2)−0.021 (3)0.029 (2)−0.041 (2)
C40.096 (3)0.107 (3)0.047 (2)−0.036 (2)0.010 (2)−0.022 (2)
C50.063 (2)0.080 (2)0.0463 (19)−0.0135 (18)0.0049 (17)0.0028 (17)
C60.0501 (19)0.0516 (17)0.0346 (15)−0.0020 (14)0.0037 (14)0.0011 (13)
C70.0527 (19)0.0597 (19)0.0523 (18)−0.0017 (15)0.0127 (15)0.0151 (14)
C80.0487 (18)0.0422 (16)0.0476 (17)−0.0058 (14)0.0077 (14)−0.0022 (14)
C90.055 (2)0.0580 (19)0.0560 (19)−0.0057 (16)0.0088 (16)0.0116 (15)
C100.053 (2)0.078 (2)0.082 (2)−0.0051 (18)0.0116 (19)0.0160 (19)
C110.055 (2)0.077 (2)0.081 (2)0.0072 (18)0.012 (2)0.007 (2)
C120.068 (2)0.0550 (19)0.066 (2)0.0146 (17)0.0066 (18)0.0096 (16)
C130.064 (2)0.0494 (18)0.0564 (19)0.0017 (16)0.0162 (16)0.0082 (15)
C140.0445 (19)0.079 (2)0.066 (2)0.0117 (16)0.0066 (16)0.0145 (17)
C150.0445 (18)0.0548 (18)0.0497 (18)0.0076 (15)0.0027 (15)0.0049 (14)
C160.051 (2)0.065 (2)0.064 (2)0.0076 (16)0.0083 (17)0.0019 (17)
C170.067 (2)0.081 (3)0.061 (2)0.020 (2)0.0015 (19)0.0083 (18)
C180.095 (3)0.067 (2)0.058 (2)0.022 (2)0.016 (2)0.0151 (17)
C190.071 (2)0.067 (2)0.078 (2)−0.0035 (18)0.019 (2)0.0073 (19)
C200.055 (2)0.069 (2)0.067 (2)−0.0023 (17)0.0032 (17)0.0048 (17)
C210.0426 (17)0.0426 (16)0.0500 (18)0.0038 (14)0.0067 (15)−0.0001 (14)
C220.0447 (16)0.0393 (15)0.0391 (15)0.0020 (13)0.0082 (13)−0.0030 (12)
C230.0482 (18)0.0458 (16)0.0438 (17)−0.0001 (14)0.0102 (15)−0.0004 (13)
C240.0536 (18)0.0520 (17)0.0372 (15)0.0009 (14)0.0068 (14)−0.0028 (13)
C250.0478 (18)0.0437 (16)0.0359 (15)−0.0039 (14)0.0048 (14)−0.0012 (12)
C260.059 (2)0.0362 (16)0.0519 (18)−0.0065 (14)0.0006 (16)−0.0020 (13)
C270.059 (2)0.0411 (16)0.0550 (18)0.0026 (14)−0.0058 (16)0.0086 (14)
C280.056 (2)0.0488 (18)0.061 (2)0.0044 (15)−0.0026 (18)0.0041 (15)
C290.060 (2)0.110 (3)0.118 (3)0.012 (2)0.017 (3)0.013 (3)
C300.089 (3)0.141 (5)0.235 (7)0.038 (3)0.021 (4)0.056 (4)

Geometric parameters (Å, °)

O1—C211.233 (3)C11—H110.9400
O2—C231.223 (3)C12—C131.402 (4)
O3—C281.333 (3)C12—H120.9400
O3—C291.461 (4)C13—H130.9400
O4—C281.200 (3)C14—C151.504 (4)
N1—C211.367 (3)C14—H14A0.9800
N1—C11.429 (3)C14—H14B0.9800
N1—C71.481 (3)C15—C161.388 (4)
N2—C231.383 (3)C15—C201.390 (4)
N2—C61.430 (3)C16—C171.392 (4)
N2—C141.477 (3)C16—H160.9400
N3—N41.322 (3)C17—C181.372 (5)
N3—C251.371 (3)C17—H170.9400
N4—N51.350 (3)C18—C191.391 (5)
N5—C261.351 (3)C18—H180.9400
N5—C271.460 (3)C19—C201.397 (4)
C1—C21.391 (4)C19—H190.9400
C1—C61.405 (4)C20—H200.9400
C2—C31.385 (5)C21—C221.524 (4)
C2—H20.9400C22—C231.528 (4)
C3—C41.389 (5)C22—C241.530 (3)
C3—H30.9400C22—H220.9900
C4—C51.376 (4)C24—C251.502 (4)
C4—H40.9400C24—H24A0.9800
C5—C61.395 (4)C24—H24B0.9800
C5—H50.9400C25—C261.363 (4)
C7—C81.520 (4)C26—H260.9400
C7—H7A0.9800C27—C281.513 (4)
C7—H7B0.9800C27—H27A0.9800
C8—C131.386 (4)C27—H27B0.9800
C8—C91.394 (4)C29—C301.475 (4)
C9—C101.390 (4)C29—H29A0.9800
C9—H90.9400C29—H29B0.9800
C10—C111.381 (4)C30—H30A0.9700
C10—H100.9400C30—H30B0.9700
C11—C121.379 (4)C30—H30C0.9700
C28—O3—C29114.8 (3)C20—C15—C14121.3 (3)
C21—N1—C1122.5 (2)C15—C16—C17120.7 (3)
C21—N1—C7117.9 (2)C15—C16—H16119.6
C1—N1—C7119.5 (2)C17—C16—H16119.6
C23—N2—C6123.3 (2)C18—C17—C16120.1 (3)
C23—N2—C14117.2 (2)C18—C17—H17120.0
C6—N2—C14118.5 (2)C16—C17—H17120.0
N4—N3—C25109.2 (2)C17—C18—C19120.3 (3)
N3—N4—N5107.2 (2)C17—C18—H18119.9
N4—N5—C26110.0 (2)C19—C18—H18119.9
N4—N5—C27120.0 (2)C18—C19—C20119.5 (3)
C26—N5—C27129.9 (2)C18—C19—H19120.3
C2—C1—C6119.6 (3)C20—C19—H19120.3
C2—C1—N1118.2 (3)C15—C20—C19120.6 (3)
C6—C1—N1122.1 (2)C15—C20—H20119.7
C3—C2—C1120.5 (3)C19—C20—H20119.7
C3—C2—H2119.7O1—C21—N1121.6 (3)
C1—C2—H2119.7O1—C21—C22122.2 (2)
C2—C3—C4119.8 (3)N1—C21—C22116.2 (2)
C2—C3—H3120.1C21—C22—C23105.7 (2)
C4—C3—H3120.1C21—C22—C24111.4 (2)
C5—C4—C3120.0 (3)C23—C22—C24112.6 (2)
C5—C4—H4120.0C21—C22—H22109.0
C3—C4—H4120.0C23—C22—H22109.0
C4—C5—C6121.1 (3)C24—C22—H22109.0
C4—C5—H5119.5O2—C23—N2122.3 (3)
C6—C5—H5119.5O2—C23—C22122.6 (2)
C5—C6—C1118.9 (3)N2—C23—C22115.0 (2)
C5—C6—N2118.9 (3)C25—C24—C22111.2 (2)
C1—C6—N2122.2 (2)C25—C24—H24A109.4
N1—C7—C8116.9 (2)C22—C24—H24A109.4
N1—C7—H7A108.1C25—C24—H24B109.4
C8—C7—H7A108.1C22—C24—H24B109.4
N1—C7—H7B108.1H24A—C24—H24B108.0
C8—C7—H7B108.1C26—C25—N3107.3 (2)
H7A—C7—H7B107.3C26—C25—C24131.7 (2)
C13—C8—C9118.1 (3)N3—C25—C24120.9 (2)
C13—C8—C7124.2 (3)N5—C26—C25106.3 (2)
C9—C8—C7117.7 (2)N5—C26—H26126.8
C10—C9—C8121.2 (3)C25—C26—H26126.8
C10—C9—H9119.4N5—C27—C28111.6 (2)
C8—C9—H9119.4N5—C27—H27A109.3
C11—C10—C9120.1 (3)C28—C27—H27A109.3
C11—C10—H10119.9N5—C27—H27B109.3
C9—C10—H10119.9C28—C27—H27B109.3
C10—C11—C12119.7 (3)H27A—C27—H27B108.0
C10—C11—H11120.2O4—C28—O3125.2 (3)
C12—C11—H11120.2O4—C28—C27125.0 (3)
C11—C12—C13120.1 (3)O3—C28—C27109.7 (3)
C11—C12—H12120.0O3—C29—C30108.4 (3)
C13—C12—H12120.0O3—C29—H29A110.0
C8—C13—C12120.9 (3)C30—C29—H29A110.0
C8—C13—H13119.6O3—C29—H29B110.0
C12—C13—H13119.6C30—C29—H29B110.0
N2—C14—C15113.5 (2)H29A—C29—H29B108.4
N2—C14—H14A108.9C29—C30—H30A109.5
C15—C14—H14A108.9C29—C30—H30B109.5
N2—C14—H14B108.9H30A—C30—H30B109.5
C15—C14—H14B108.9C29—C30—H30C109.5
H14A—C14—H14B107.7H30A—C30—H30C109.5
C16—C15—C20118.8 (3)H30B—C30—H30C109.5
C16—C15—C14119.9 (3)
C25—N3—N4—N50.5 (3)C15—C16—C17—C18−0.6 (5)
N3—N4—N5—C26−0.5 (3)C16—C17—C18—C190.0 (5)
N3—N4—N5—C27−176.5 (2)C17—C18—C19—C200.4 (5)
C21—N1—C1—C2−135.6 (3)C16—C15—C20—C19−0.3 (4)
C7—N1—C1—C248.8 (4)C14—C15—C20—C19−177.5 (3)
C21—N1—C1—C647.6 (4)C18—C19—C20—C15−0.3 (5)
C7—N1—C1—C6−128.0 (3)C1—N1—C21—O1−176.6 (2)
C6—C1—C2—C31.4 (5)C7—N1—C21—O1−0.9 (4)
N1—C1—C2—C3−175.5 (3)C1—N1—C21—C220.8 (4)
C1—C2—C3—C40.8 (6)C7—N1—C21—C22176.5 (2)
C2—C3—C4—C5−2.5 (6)O1—C21—C22—C23101.2 (3)
C3—C4—C5—C62.1 (5)N1—C21—C22—C23−76.1 (3)
C4—C5—C6—C10.0 (4)O1—C21—C22—C24−21.4 (3)
C4—C5—C6—N2178.2 (3)N1—C21—C22—C24161.2 (2)
C2—C1—C6—C5−1.8 (4)C6—N2—C23—O2−173.5 (2)
N1—C1—C6—C5175.0 (2)C14—N2—C23—O2−4.5 (4)
C2—C1—C6—N2−179.8 (3)C6—N2—C23—C229.6 (4)
N1—C1—C6—N2−3.1 (4)C14—N2—C23—C22178.7 (2)
C23—N2—C6—C5132.3 (3)C21—C22—C23—O2−108.4 (3)
C14—N2—C6—C5−36.6 (4)C24—C22—C23—O213.5 (4)
C23—N2—C6—C1−49.6 (4)C21—C22—C23—N268.5 (3)
C14—N2—C6—C1141.4 (3)C24—C22—C23—N2−169.7 (2)
C21—N1—C7—C877.6 (3)C21—C22—C24—C25−80.8 (3)
C1—N1—C7—C8−106.6 (3)C23—C22—C24—C25160.6 (2)
N1—C7—C8—C13−13.9 (4)N4—N3—C25—C26−0.3 (3)
N1—C7—C8—C9169.2 (2)N4—N3—C25—C24−177.0 (2)
C13—C8—C9—C100.2 (4)C22—C24—C25—C26128.0 (3)
C7—C8—C9—C10177.3 (3)C22—C24—C25—N3−56.2 (3)
C8—C9—C10—C11−1.4 (5)N4—N5—C26—C250.3 (3)
C9—C10—C11—C121.5 (5)C27—N5—C26—C25175.8 (3)
C10—C11—C12—C13−0.4 (5)N3—C25—C26—N50.0 (3)
C9—C8—C13—C120.9 (4)C24—C25—C26—N5176.2 (3)
C7—C8—C13—C12−176.0 (3)N4—N5—C27—C2893.4 (3)
C11—C12—C13—C8−0.8 (5)C26—N5—C27—C28−81.7 (3)
C23—N2—C14—C15136.3 (3)C29—O3—C28—O4−2.8 (5)
C6—N2—C14—C15−54.1 (4)C29—O3—C28—C27176.7 (3)
N2—C14—C15—C16139.8 (3)N5—C27—C28—O4−9.6 (4)
N2—C14—C15—C20−43.0 (4)N5—C27—C28—O3170.8 (2)
C20—C15—C16—C170.7 (4)C28—O3—C29—C30−169.4 (3)
C14—C15—C16—C17178.0 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2708).

References

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