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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o3039.
Published online 2010 October 31. doi:  10.1107/S1600536810044120
PMCID: PMC3009227

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

Abstract

In the title compound, C18H21N5O4, the diazepine ring adopts a boat conformation with the triazolylmethyl-bearing C atom as the prow and the C atoms at the ring junction as the stern.

Related literature

For the structure of 1,5-dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione, see: Dardouri et al. (2010 [triangle]).

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Object name is e-66-o3039-scheme1.jpg

Experimental

Crystal data

  • C18H21N5O4
  • M r = 371.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3039-efi1.jpg
  • a = 8.5452 (2) Å
  • b = 15.9993 (5) Å
  • c = 13.9215 (4) Å
  • β = 106.853 (1)°
  • V = 1821.56 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.40 × 0.10 × 0.05 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 15511 measured reflections
  • 4129 independent reflections
  • 2909 reflections with I > 2σ(I)
  • R int = 0.037
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.124
  • S = 1.03
  • 4129 reflections
  • 247 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.31 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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044120/bt5398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044120/bt5398Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

1,5-Dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione, whose synthesis was reported recently (Dardouri et al., 2010), possess an acetylenic linkage that can be exploited for the synthesis of other 1,5-benzodiazepine-2,4-dione derivatives. In this study, the compound is reacted with ethyl 2-azidoacetate to yield the title compound (Scheme I, Fig. 1). The ester provides three nitrogen atoms necessary for the formation of the triazolyl ring.

Experimental

To a solution of 3-propargyl-1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.23 g,1 mmol) in a t-butyl alcohol/water mixture (1:2, 8 ml) was added copper sulfate pentahydrate (0.25 g,1 mmol), sodium ascorbate (0.29 g, 2 mmol) and ethyl 2-azidoacetate (0.64 g, 5 mmol). The mixture was stirred for two hours. Water (20 ml) was added and the organic compound was extracted with ethyl acetate (2 x 20 ml). The extracts were washed with brine and then dried over sodium sulfate. The compound was recrystallized from an n-hexane/ethyl acetate mixture to give colorless crystals.

Refinement

H-atoms were placed in calculated positions (C—H 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C18H21N5O4 at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C18H21N5O4F(000) = 784
Mr = 371.40Dx = 1.354 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3798 reflections
a = 8.5452 (2) Åθ = 2.5–26.4°
b = 15.9993 (5) ŵ = 0.10 mm1
c = 13.9215 (4) ÅT = 293 K
β = 106.853 (1)°Prism, colorless
V = 1821.56 (9) Å30.40 × 0.10 × 0.05 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer2909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
graphiteθmax = 27.5°, θmin = 2.8°
[var phi] and ω scansh = −10→10
15511 measured reflectionsk = −20→20
4129 independent reflectionsl = −18→18

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.052P)2 + 0.6008P] where P = (Fo2 + 2Fc2)/3
4129 reflections(Δ/σ)max = 0.001
247 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.31 e Å3

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

xyzUiso*/Ueq
O10.56199 (17)0.18555 (8)0.67466 (9)0.0438 (3)
O20.81954 (18)0.21921 (9)0.49678 (10)0.0505 (4)
O30.41269 (16)0.12018 (9)−0.04809 (9)0.0440 (3)
O40.25337 (19)0.10260 (14)0.05096 (12)0.0829 (7)
N10.78013 (17)0.10102 (8)0.73772 (10)0.0285 (3)
N20.96549 (17)0.11692 (10)0.59493 (10)0.0344 (4)
N30.52214 (17)0.02996 (9)0.35097 (10)0.0314 (3)
N40.52862 (17)0.02234 (9)0.25819 (10)0.0328 (3)
N50.52498 (17)0.10028 (9)0.22117 (10)0.0291 (3)
C10.88147 (19)0.03536 (10)0.72159 (12)0.0271 (4)
C20.8961 (2)−0.03761 (11)0.77820 (13)0.0347 (4)
H20.8390−0.04260.82550.042*
C30.9939 (2)−0.10250 (12)0.76516 (15)0.0421 (5)
H31.0037−0.15050.80420.050*
C41.0772 (2)−0.09629 (13)0.69423 (15)0.0449 (5)
H41.1407−0.14070.68400.054*
C51.0662 (2)−0.02442 (13)0.63862 (13)0.0395 (5)
H51.1237−0.02050.59140.047*
C60.97042 (19)0.04275 (11)0.65161 (12)0.0300 (4)
C70.7764 (2)0.11896 (12)0.84068 (13)0.0385 (4)
H7A0.76590.17810.84860.058*
H7B0.87580.09960.88750.058*
H7C0.68490.09090.85310.058*
C80.6620 (2)0.13566 (10)0.66069 (12)0.0301 (4)
C90.6685 (2)0.11352 (10)0.55590 (11)0.0263 (3)
H90.67980.05280.55140.032*
C100.8228 (2)0.15520 (11)0.54480 (12)0.0332 (4)
C111.1183 (2)0.15061 (15)0.58176 (15)0.0499 (5)
H11A1.12090.21010.59090.075*
H11B1.12370.13780.51540.075*
H11C1.21000.12580.63040.075*
C120.5152 (2)0.14153 (11)0.47517 (12)0.0314 (4)
H12A0.41950.11940.49040.038*
H12B0.50830.20200.47550.038*
C130.51605 (19)0.11257 (10)0.37318 (12)0.0274 (3)
C140.5173 (2)0.15758 (11)0.29023 (12)0.0295 (4)
H140.51360.21540.28300.035*
C150.5444 (2)0.11311 (12)0.12218 (12)0.0339 (4)
H15A0.61630.07030.10960.041*
H15B0.59630.16680.12070.041*
C160.3849 (2)0.11069 (11)0.03967 (13)0.0366 (4)
C170.2699 (3)0.11868 (14)−0.13697 (14)0.0487 (5)
H17A0.19600.0748−0.12940.058*
H17B0.30510.1058−0.19560.058*
C180.1815 (2)0.19999 (12)−0.15270 (14)0.0435 (5)
H18A0.09000.1969−0.21210.065*
H18B0.25420.2436−0.16030.065*
H18C0.14310.2120−0.09580.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0564 (9)0.0414 (7)0.0342 (7)0.0164 (6)0.0141 (6)−0.0056 (6)
O20.0584 (9)0.0477 (8)0.0410 (8)−0.0153 (7)0.0074 (7)0.0153 (6)
O30.0389 (7)0.0690 (9)0.0205 (6)0.0060 (6)0.0030 (5)−0.0024 (6)
O40.0371 (9)0.1597 (19)0.0459 (10)−0.0232 (10)0.0022 (7)0.0413 (11)
N10.0337 (8)0.0327 (7)0.0201 (7)−0.0024 (6)0.0091 (6)−0.0031 (5)
N20.0301 (8)0.0491 (9)0.0242 (7)−0.0106 (7)0.0080 (6)0.0014 (6)
N30.0320 (8)0.0344 (8)0.0264 (7)−0.0013 (6)0.0063 (6)0.0015 (6)
N40.0352 (8)0.0332 (8)0.0274 (7)−0.0031 (6)0.0050 (6)0.0005 (6)
N50.0287 (7)0.0341 (8)0.0223 (7)−0.0019 (6)0.0040 (5)0.0016 (6)
C10.0246 (8)0.0334 (8)0.0217 (8)−0.0037 (7)0.0043 (6)−0.0038 (6)
C20.0307 (9)0.0398 (10)0.0312 (9)−0.0051 (7)0.0053 (7)0.0024 (7)
C30.0365 (10)0.0369 (10)0.0446 (11)0.0011 (8)−0.0013 (8)0.0032 (8)
C40.0312 (10)0.0519 (12)0.0437 (11)0.0111 (8)−0.0017 (8)−0.0094 (9)
C50.0256 (9)0.0631 (13)0.0273 (9)0.0038 (8)0.0035 (7)−0.0092 (9)
C60.0239 (8)0.0429 (10)0.0203 (8)−0.0053 (7)0.0018 (6)−0.0034 (7)
C70.0472 (11)0.0469 (11)0.0227 (9)−0.0019 (9)0.0119 (8)−0.0072 (8)
C80.0376 (10)0.0269 (8)0.0262 (8)−0.0007 (7)0.0098 (7)−0.0017 (6)
C90.0310 (9)0.0263 (8)0.0214 (8)0.0005 (7)0.0069 (6)−0.0008 (6)
C100.0395 (10)0.0387 (9)0.0204 (8)−0.0080 (8)0.0069 (7)−0.0015 (7)
C110.0375 (11)0.0799 (15)0.0324 (10)−0.0239 (10)0.0104 (8)0.0009 (10)
C120.0314 (9)0.0361 (9)0.0259 (8)0.0072 (7)0.0072 (7)0.0018 (7)
C130.0229 (8)0.0319 (8)0.0255 (8)0.0013 (6)0.0042 (6)0.0024 (7)
C140.0299 (9)0.0296 (8)0.0272 (8)0.0010 (7)0.0051 (7)0.0016 (7)
C150.0329 (9)0.0448 (10)0.0225 (8)−0.0031 (8)0.0055 (7)0.0001 (7)
C160.0348 (10)0.0418 (10)0.0293 (9)−0.0072 (8)0.0033 (7)0.0055 (7)
C170.0509 (12)0.0617 (13)0.0231 (9)0.0071 (10)−0.0056 (8)−0.0067 (9)
C180.0438 (11)0.0441 (11)0.0352 (10)−0.0068 (9)−0.0002 (8)0.0007 (8)

Geometric parameters (Å, °)

O1—C81.225 (2)C5—H50.9300
O2—C101.219 (2)C7—H7A0.9600
O3—C161.319 (2)C7—H7B0.9600
O3—C171.464 (2)C7—H7C0.9600
O4—C161.186 (2)C8—C91.518 (2)
N1—C81.360 (2)C9—C121.525 (2)
N1—C11.420 (2)C9—C101.524 (2)
N1—C71.471 (2)C9—H90.9800
N2—C101.362 (2)C11—H11A0.9600
N2—C61.419 (2)C11—H11B0.9600
N2—C111.473 (2)C11—H11C0.9600
N3—N41.3145 (19)C12—C131.495 (2)
N3—C131.362 (2)C12—H12A0.9700
N4—N51.3462 (19)C12—H12B0.9700
N5—C141.344 (2)C13—C141.364 (2)
N5—C151.450 (2)C14—H140.9300
C1—C21.394 (2)C15—C161.507 (2)
C1—C61.404 (2)C15—H15A0.9700
C2—C31.377 (3)C15—H15B0.9700
C2—H20.9300C17—C181.489 (3)
C3—C41.378 (3)C17—H17A0.9700
C3—H30.9300C17—H17B0.9700
C4—C51.374 (3)C18—H18A0.9600
C4—H40.9300C18—H18B0.9600
C5—C61.394 (3)C18—H18C0.9600
C16—O3—C17116.81 (15)C10—C9—H9108.9
C8—N1—C1121.62 (13)O2—C10—N2122.21 (16)
C8—N1—C7117.89 (14)O2—C10—C9122.71 (16)
C1—N1—C7119.01 (14)N2—C10—C9115.05 (15)
C10—N2—C6122.59 (14)N2—C11—H11A109.5
C10—N2—C11117.80 (16)N2—C11—H11B109.5
C6—N2—C11119.40 (15)H11A—C11—H11B109.5
N4—N3—C13109.17 (13)N2—C11—H11C109.5
N3—N4—N5106.71 (13)H11A—C11—H11C109.5
C14—N5—N4111.01 (13)H11B—C11—H11C109.5
C14—N5—C15128.78 (14)C13—C12—C9111.66 (13)
N4—N5—C15119.93 (14)C13—C12—H12A109.3
C2—C1—C6119.01 (15)C9—C12—H12A109.3
C2—C1—N1119.29 (15)C13—C12—H12B109.3
C6—C1—N1121.68 (15)C9—C12—H12B109.3
C3—C2—C1121.03 (17)H12A—C12—H12B107.9
C3—C2—H2119.5C14—C13—N3108.06 (15)
C1—C2—H2119.5C14—C13—C12130.07 (15)
C2—C3—C4119.94 (18)N3—C13—C12121.82 (14)
C2—C3—H3120.0N5—C14—C13105.05 (15)
C4—C3—H3120.0N5—C14—H14127.5
C5—C4—C3119.93 (18)C13—C14—H14127.5
C5—C4—H4120.0N5—C15—C16113.16 (14)
C3—C4—H4120.0N5—C15—H15A108.9
C4—C5—C6121.26 (17)C16—C15—H15A108.9
C4—C5—H5119.4N5—C15—H15B108.9
C6—C5—H5119.4C16—C15—H15B108.9
C5—C6—C1118.78 (16)H15A—C15—H15B107.8
C5—C6—N2119.78 (15)O4—C16—O3124.56 (17)
C1—C6—N2121.44 (15)O4—C16—C15125.75 (17)
N1—C7—H7A109.5O3—C16—C15109.69 (15)
N1—C7—H7B109.5O3—C17—C18111.90 (16)
H7A—C7—H7B109.5O3—C17—H17A109.2
N1—C7—H7C109.5C18—C17—H17A109.2
H7A—C7—H7C109.5O3—C17—H17B109.2
H7B—C7—H7C109.5C18—C17—H17B109.2
O1—C8—N1122.20 (15)H17A—C17—H17B107.9
O1—C8—C9121.75 (15)C17—C18—H18A109.5
N1—C8—C9115.91 (14)C17—C18—H18B109.5
C8—C9—C12112.12 (13)H18A—C18—H18B109.5
C8—C9—C10105.62 (13)C17—C18—H18C109.5
C12—C9—C10112.32 (14)H18A—C18—H18C109.5
C8—C9—H9108.9H18B—C18—H18C109.5
C12—C9—H9108.9
C13—N3—N4—N5−0.60 (17)O1—C8—C9—C10107.96 (18)
N3—N4—N5—C140.41 (17)N1—C8—C9—C10−67.92 (18)
N3—N4—N5—C15174.79 (13)C6—N2—C10—O2179.53 (16)
C8—N1—C1—C2−127.81 (17)C11—N2—C10—O2−5.9 (3)
C7—N1—C1—C238.0 (2)C6—N2—C10—C91.3 (2)
C8—N1—C1—C653.7 (2)C11—N2—C10—C9175.88 (15)
C7—N1—C1—C6−140.50 (16)C8—C9—C10—O2−103.15 (18)
C6—C1—C2—C3−1.1 (2)C12—C9—C10—O219.4 (2)
N1—C1—C2—C3−179.65 (15)C8—C9—C10—N275.09 (17)
C1—C2—C3—C4−0.9 (3)C12—C9—C10—N2−162.40 (14)
C2—C3—C4—C51.8 (3)C8—C9—C12—C13−174.76 (14)
C3—C4—C5—C6−0.7 (3)C10—C9—C12—C1366.48 (18)
C4—C5—C6—C1−1.3 (2)N4—N3—C13—C140.58 (18)
C4—C5—C6—N2178.22 (15)N4—N3—C13—C12−177.28 (14)
C2—C1—C6—C52.2 (2)C9—C12—C13—C14−117.25 (19)
N1—C1—C6—C5−179.29 (15)C9—C12—C13—N360.1 (2)
C2—C1—C6—N2−177.35 (14)N4—N5—C14—C13−0.06 (18)
N1—C1—C6—N21.2 (2)C15—N5—C14—C13−173.80 (15)
C10—N2—C6—C5131.51 (17)N3—C13—C14—N5−0.31 (18)
C11—N2—C6—C5−43.0 (2)C12—C13—C14—N5177.32 (16)
C10—N2—C6—C1−49.0 (2)C14—N5—C15—C16−97.7 (2)
C11—N2—C6—C1136.53 (17)N4—N5—C15—C1689.08 (19)
C1—N1—C8—O1171.63 (16)C17—O3—C16—O4−1.3 (3)
C7—N1—C8—O15.6 (2)C17—O3—C16—C15179.53 (16)
C1—N1—C8—C9−12.5 (2)N5—C15—C16—O42.8 (3)
C7—N1—C8—C9−178.49 (14)N5—C15—C16—O3−178.05 (15)
O1—C8—C9—C12−14.7 (2)C16—O3—C17—C1879.5 (2)
N1—C8—C9—C12169.44 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5398).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dardouri, R., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1797. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography