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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o632.
Published online 2010 February 13. doi:  10.1107/S1600536810005313
PMCID: PMC2983517

3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-1,5-benzodiazepine-2,4-dione

Abstract

The title compound, C21H21N5O2, is a 1,4-dimethyl-1,2,3-triazole having dimethyl­benzodiazepindione and phenyl substituents on each methyl group; the substituents are positioned on opposite sides of the five-membered ring. The seven-membered fused-ring of the larger substituent adopts a boat-shaped conformation (with the methine C atom as the prow).

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 [triangle]).

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Object name is e-66-0o632-scheme1.jpg

Experimental

Crystal data

  • C21H21N5O2
  • M r = 375.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o632-efi1.jpg
  • a = 8.3380 (3) Å
  • b = 9.1033 (3) Å
  • c = 13.4796 (4) Å
  • α = 95.385 (2)°
  • β = 107.840 (2)°
  • γ = 101.768 (2)°
  • V = 939.97 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.28 × 0.18 × 0.08 mm

Data collection

  • Bruker APEXII diffractometer
  • 7973 measured reflections
  • 3279 independent reflections
  • 2132 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.141
  • S = 1.05
  • 3279 reflections
  • 255 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005313/bt5192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005313/bt5192Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

To a solution of 1,5-dimethyl-3-propargyl-1,5-benzodiazepine-2,4-dione (1 mmol) in t-butyl alcohol/water (1/2, 8 ml) was added copper sulfate pentahydrate (1 mmol), sodium ascorbate (2 mmol) and benzyl azide (5 mmol). The mixture was stirred for 8 h. The solution was then diluted with water (20 ml) and the organic compound extracted with ethyl acetate (2 × 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 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C21H21N5O2 at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C21H21N5O2Z = 2
Mr = 375.43F(000) = 396
Triclinic, P1Dx = 1.326 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3380 (3) ÅCell parameters from 1894 reflections
b = 9.1033 (3) Åθ = 2.3–26.8°
c = 13.4796 (4) ŵ = 0.09 mm1
α = 95.385 (2)°T = 293 K
β = 107.840 (2)°Block, colourless
γ = 101.768 (2)°0.28 × 0.18 × 0.08 mm
V = 939.97 (5) Å3

Data collection

Bruker APEXII diffractometer2132 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
graphiteθmax = 25.0°, θmin = 1.6°
[var phi] and ω scansh = −8→9
7973 measured reflectionsk = −10→10
3279 independent reflectionsl = −16→15

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
3279 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.22 e Å3

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

xyzUiso*/Ueq
O10.50707 (19)0.14271 (17)0.38773 (13)0.0383 (4)
O20.8254 (2)0.2153 (2)0.23619 (15)0.0501 (5)
N10.8448 (2)0.2106 (2)0.71289 (16)0.0366 (5)
N20.9062 (2)0.3607 (2)0.71872 (16)0.0376 (5)
N30.9231 (2)0.3802 (2)0.62613 (16)0.0359 (5)
N40.4763 (2)0.37357 (19)0.34845 (14)0.0283 (4)
N50.6925 (2)0.4101 (2)0.21476 (15)0.0310 (5)
C10.9776 (3)0.1642 (3)0.89419 (19)0.0359 (6)
C21.0765 (3)0.0598 (3)0.8911 (2)0.0409 (6)
H21.0396−0.01900.83390.049*
C31.2289 (4)0.0720 (4)0.9720 (3)0.0650 (9)
H31.29430.00130.96940.078*
C41.2843 (5)0.1865 (6)1.0557 (3)0.0935 (15)
H41.38680.19281.11060.112*
C51.1909 (6)0.2932 (5)1.0604 (3)0.0947 (16)
H51.23120.37311.11710.114*
C61.0353 (5)0.2807 (3)0.9796 (2)0.0610 (9)
H60.96990.35120.98310.073*
C70.8123 (3)0.1525 (3)0.8049 (2)0.0442 (7)
H7A0.74760.04680.78360.053*
H7B0.74150.20960.82940.053*
C80.8216 (3)0.1340 (3)0.6177 (2)0.0364 (6)
H80.77990.02960.59440.044*
C90.8726 (3)0.2424 (3)0.56202 (19)0.0321 (6)
C100.8729 (3)0.2271 (3)0.45103 (19)0.0346 (6)
H10A0.82790.12090.41810.042*
H10B0.99150.25900.45150.042*
C110.5716 (3)0.2698 (2)0.37552 (18)0.0282 (5)
C120.7630 (3)0.3225 (2)0.38576 (18)0.0284 (5)
H120.80700.42920.42020.034*
C130.7673 (3)0.3110 (3)0.27368 (19)0.0324 (6)
C140.6468 (3)0.5362 (2)0.26045 (17)0.0286 (5)
C150.6992 (3)0.6803 (3)0.2368 (2)0.0357 (6)
H150.76070.69190.18980.043*
C160.6620 (3)0.8055 (3)0.2814 (2)0.0403 (6)
H160.69770.90040.26410.048*
C170.5715 (3)0.7908 (3)0.3521 (2)0.0385 (6)
H170.55000.87600.38440.046*
C180.5137 (3)0.6485 (2)0.37394 (19)0.0324 (5)
H180.45130.63840.42050.039*
C190.5468 (3)0.5196 (2)0.32765 (17)0.0268 (5)
C200.2922 (3)0.3329 (3)0.3420 (2)0.0364 (6)
H20A0.23570.23510.29850.055*
H20B0.23560.40800.31180.055*
H20C0.28570.32930.41170.055*
C210.7053 (3)0.4078 (3)0.1087 (2)0.0440 (7)
H21A0.81970.46260.11380.066*
H21B0.62070.45490.06720.066*
H21C0.68410.30440.07560.066*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0331 (9)0.0258 (9)0.0594 (12)0.0034 (7)0.0207 (8)0.0141 (8)
O20.0635 (12)0.0451 (11)0.0596 (12)0.0259 (9)0.0373 (10)0.0104 (9)
N10.0281 (10)0.0379 (12)0.0463 (13)0.0062 (9)0.0139 (9)0.0187 (10)
N20.0316 (11)0.0349 (12)0.0476 (13)0.0078 (9)0.0133 (10)0.0139 (9)
N30.0278 (10)0.0370 (12)0.0461 (13)0.0085 (9)0.0138 (9)0.0160 (10)
N40.0219 (9)0.0264 (10)0.0388 (12)0.0037 (8)0.0138 (8)0.0080 (8)
N50.0315 (10)0.0314 (11)0.0333 (11)0.0061 (8)0.0163 (9)0.0067 (9)
C10.0399 (13)0.0350 (14)0.0344 (14)−0.0005 (11)0.0197 (11)0.0095 (11)
C20.0387 (14)0.0420 (15)0.0435 (16)0.0041 (11)0.0176 (12)0.0138 (12)
C30.0380 (16)0.089 (2)0.070 (2)0.0062 (16)0.0172 (16)0.048 (2)
C40.061 (2)0.113 (3)0.060 (3)−0.043 (2)−0.0130 (18)0.048 (3)
C50.138 (4)0.069 (3)0.0316 (19)−0.049 (3)0.014 (2)0.0020 (17)
C60.099 (2)0.0374 (16)0.0501 (19)−0.0039 (15)0.0430 (19)0.0055 (13)
C70.0399 (14)0.0494 (16)0.0526 (17)0.0084 (12)0.0261 (13)0.0233 (13)
C80.0334 (13)0.0277 (13)0.0478 (16)0.0042 (10)0.0139 (12)0.0108 (11)
C90.0200 (11)0.0302 (13)0.0494 (15)0.0079 (9)0.0128 (10)0.0147 (11)
C100.0288 (12)0.0313 (13)0.0501 (16)0.0102 (10)0.0185 (11)0.0132 (11)
C110.0291 (12)0.0243 (12)0.0338 (13)0.0043 (9)0.0153 (10)0.0067 (9)
C120.0272 (11)0.0234 (11)0.0385 (14)0.0054 (9)0.0162 (10)0.0074 (10)
C130.0292 (12)0.0279 (13)0.0432 (15)0.0034 (10)0.0190 (11)0.0055 (11)
C140.0223 (11)0.0300 (12)0.0331 (13)0.0059 (9)0.0084 (10)0.0081 (10)
C150.0267 (12)0.0379 (14)0.0472 (15)0.0062 (10)0.0170 (11)0.0185 (12)
C160.0310 (13)0.0294 (13)0.0630 (18)0.0065 (10)0.0165 (12)0.0194 (12)
C170.0321 (13)0.0273 (13)0.0577 (17)0.0101 (10)0.0153 (12)0.0076 (11)
C180.0254 (11)0.0316 (13)0.0411 (14)0.0088 (10)0.0109 (10)0.0068 (10)
C190.0229 (11)0.0244 (12)0.0322 (13)0.0053 (9)0.0078 (9)0.0070 (9)
C200.0234 (12)0.0421 (14)0.0460 (15)0.0032 (10)0.0164 (11)0.0116 (11)
C210.0493 (15)0.0498 (16)0.0386 (15)0.0088 (12)0.0242 (13)0.0103 (12)

Geometric parameters (Å, °)

O1—C111.221 (2)C7—H7B0.9700
O2—C131.221 (3)C8—C91.372 (3)
N1—C81.340 (3)C8—H80.9300
N1—N21.344 (3)C9—C101.490 (3)
N1—C71.470 (3)C10—C121.531 (3)
N2—N31.322 (3)C10—H10A0.9700
N3—C91.362 (3)C10—H10B0.9700
N4—C111.361 (3)C11—C121.528 (3)
N4—C191.429 (3)C12—C131.517 (3)
N4—C201.477 (3)C12—H120.9800
N5—C131.376 (3)C14—C151.394 (3)
N5—C141.425 (3)C14—C191.406 (3)
N5—C211.464 (3)C15—C161.374 (3)
C1—C61.380 (4)C15—H150.9300
C1—C21.385 (3)C16—C171.385 (3)
C1—C71.503 (4)C16—H160.9300
C2—C31.374 (4)C17—C181.379 (3)
C2—H20.9300C17—H170.9300
C3—C41.355 (6)C18—C191.394 (3)
C3—H30.9300C18—H180.9300
C4—C51.371 (6)C20—H20A0.9600
C4—H40.9300C20—H20B0.9600
C5—C61.390 (5)C20—H20C0.9600
C5—H50.9300C21—H21A0.9600
C6—H60.9300C21—H21B0.9600
C7—H7A0.9700C21—H21C0.9600
C8—N1—N2111.21 (19)C12—C10—H10B109.2
C8—N1—C7129.2 (2)H10A—C10—H10B107.9
N2—N1—C7119.6 (2)O1—C11—N4122.12 (19)
N3—N2—N1106.65 (19)O1—C11—C12122.85 (19)
N2—N3—C9109.22 (18)N4—C11—C12115.00 (18)
C11—N4—C19123.05 (17)C13—C12—C11105.92 (18)
C11—N4—C20117.89 (17)C13—C12—C10112.28 (18)
C19—N4—C20119.06 (17)C11—C12—C10111.64 (17)
C13—N5—C14122.66 (19)C13—C12—H12109.0
C13—N5—C21116.48 (19)C11—C12—H12109.0
C14—N5—C21118.77 (18)C10—C12—H12109.0
C6—C1—C2118.8 (3)O2—C13—N5121.9 (2)
C6—C1—C7120.7 (3)O2—C13—C12122.3 (2)
C2—C1—C7120.4 (2)N5—C13—C12115.6 (2)
C3—C2—C1120.4 (3)C15—C14—C19118.5 (2)
C3—C2—H2119.8C15—C14—N5119.6 (2)
C1—C2—H2119.8C19—C14—N5121.94 (19)
C4—C3—C2120.4 (3)C16—C15—C14121.4 (2)
C4—C3—H3119.8C16—C15—H15119.3
C2—C3—H3119.8C14—C15—H15119.3
C3—C4—C5120.7 (3)C15—C16—C17120.2 (2)
C3—C4—H4119.7C15—C16—H16119.9
C5—C4—H4119.7C17—C16—H16119.9
C4—C5—C6119.4 (3)C18—C17—C16119.3 (2)
C4—C5—H5120.3C18—C17—H17120.4
C6—C5—H5120.3C16—C17—H17120.4
C1—C6—C5120.3 (3)C17—C18—C19121.4 (2)
C1—C6—H6119.9C17—C18—H18119.3
C5—C6—H6119.9C19—C18—H18119.3
N1—C7—C1112.38 (19)C18—C19—C14119.15 (19)
N1—C7—H7A109.1C18—C19—N4119.24 (19)
C1—C7—H7A109.1C14—C19—N4121.60 (19)
N1—C7—H7B109.1N4—C20—H20A109.5
C1—C7—H7B109.1N4—C20—H20B109.5
H7A—C7—H7B107.9H20A—C20—H20B109.5
N1—C8—C9105.3 (2)N4—C20—H20C109.5
N1—C8—H8127.4H20A—C20—H20C109.5
C9—C8—H8127.4H20B—C20—H20C109.5
N3—C9—C8107.7 (2)N5—C21—H21A109.5
N3—C9—C10122.0 (2)N5—C21—H21B109.5
C8—C9—C10130.3 (2)H21A—C21—H21B109.5
C9—C10—C12112.07 (18)N5—C21—H21C109.5
C9—C10—H10A109.2H21A—C21—H21C109.5
C12—C10—H10A109.2H21B—C21—H21C109.5
C9—C10—H10B109.2
C8—N1—N2—N3−0.3 (2)N4—C11—C12—C10160.55 (19)
C7—N1—N2—N3179.89 (18)C9—C10—C12—C13178.25 (18)
N1—N2—N3—C90.0 (2)C9—C10—C12—C11−63.0 (2)
C6—C1—C2—C30.4 (3)C14—N5—C13—O2−170.7 (2)
C7—C1—C2—C3179.0 (2)C21—N5—C13—O2−7.4 (3)
C1—C2—C3—C4−0.2 (4)C14—N5—C13—C1212.8 (3)
C2—C3—C4—C5−0.9 (5)C21—N5—C13—C12176.14 (18)
C3—C4—C5—C61.8 (5)C11—C12—C13—O2−109.6 (2)
C2—C1—C6—C50.5 (4)C10—C12—C13—O212.5 (3)
C7—C1—C6—C5−178.1 (2)C11—C12—C13—N566.9 (2)
C4—C5—C6—C1−1.6 (5)C10—C12—C13—N5−171.04 (18)
C8—N1—C7—C1110.1 (3)C13—N5—C14—C15130.3 (2)
N2—N1—C7—C1−70.1 (3)C21—N5—C14—C15−32.6 (3)
C6—C1—C7—N1100.6 (3)C13—N5—C14—C19−50.9 (3)
C2—C1—C7—N1−78.0 (3)C21—N5—C14—C19146.1 (2)
N2—N1—C8—C90.5 (2)C19—C14—C15—C163.0 (3)
C7—N1—C8—C9−179.7 (2)N5—C14—C15—C16−178.2 (2)
N2—N3—C9—C80.3 (2)C14—C15—C16—C170.4 (4)
N2—N3—C9—C10178.56 (19)C15—C16—C17—C18−2.4 (4)
N1—C8—C9—N3−0.5 (2)C16—C17—C18—C191.0 (3)
N1—C8—C9—C10−178.5 (2)C17—C18—C19—C142.4 (3)
N3—C9—C10—C12−56.4 (3)C17—C18—C19—N4−176.7 (2)
C8—C9—C10—C12121.4 (2)C15—C14—C19—C18−4.3 (3)
C19—N4—C11—O1−176.2 (2)N5—C14—C19—C18176.90 (19)
C20—N4—C11—O14.7 (3)C15—C14—C19—N4174.74 (18)
C19—N4—C11—C121.9 (3)N5—C14—C19—N4−4.0 (3)
C20—N4—C11—C12−177.20 (19)C11—N4—C19—C18−132.9 (2)
O1—C11—C12—C13101.1 (2)C20—N4—C19—C1846.1 (3)
N4—C11—C12—C13−76.9 (2)C11—N4—C19—C1448.0 (3)
O1—C11—C12—C10−21.4 (3)C20—N4—C19—C14−132.9 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5192).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mondieig, M., Négrier, Ph., Léger, J. M., Benali, B., Lazar, Z., Elassyry, A., Jarmouni, C., Lakhrissi, B. & Massoui, M. (2005). Anal. Sci. X-Ray Struct. Anal. Online, 21, x145–x146.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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