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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o633.
Published online 2010 February 13. doi:  10.1107/S1600536810005325
PMCID: PMC2983709

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

Abstract

In the title compound, C21H21N5O2·H2O, the seven-membered ring adopts a boat-shaped conformation with the methine C atom as the prow. In the crystal, the water mol­ecule links adjacent mol­ecules by O—H(...)O and O—H(...)N hydrogen bonds into a zigzag chain running along the c axis of the monoclinic cell.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 [triangle]). For the water-free structure of 1-benzyl-4-[(1,5-dimethyl-2,4-dioxobenzo-1,5-diazepin-3-yl)meth­yl]-1,2,3-triazole, see: Dardouri et al. (2010 [triangle]).

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Object name is e-66-0o633-scheme1.jpg

Experimental

Crystal data

  • C21H21N5O2·H2O
  • M r = 393.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o633-efi1.jpg
  • a = 9.6002 (1) Å
  • b = 11.9497 (2) Å
  • c = 17.0860 (2) Å
  • β = 92.527 (1)°
  • V = 1958.19 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 193 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker APEXII diffractometer
  • 34134 measured reflections
  • 4673 independent reflections
  • 3454 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.108
  • S = 1.02
  • 4673 reflections
  • 272 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.24 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]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005325/bt5193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005325/bt5193Isup2.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 (8.26 × 10 -4 mol) in toluene (15 ml) was added benzyl azide (9.91 × 10 -4 mol). The mixture was stirred under reflux and the reaction was monitored by thin layer chromatography. On completion of the reaction, the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 2/1). Crystals were obtained when the solvent was allowed to evaporate.

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). The water H atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of O—H 0.84 (1) Å.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C21H21N5O2.H2O at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C21H21N5O2·H2OF(000) = 832
Mr = 393.44Dx = 1.335 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7427 reflections
a = 9.6002 (1) Åθ = 2.1–28.3°
b = 11.9497 (2) ŵ = 0.09 mm1
c = 17.0860 (2) ÅT = 193 K
β = 92.527 (1)°Block, colourless
V = 1958.19 (4) Å30.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker APEXII diffractometer3454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
graphiteθmax = 27.5°, θmin = 2.7°
[var phi] and ω scansh = −12→12
34134 measured reflectionsk = −15→15
4673 independent reflectionsl = −22→22

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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0487P)2 + 0.4622P] where P = (Fo2 + 2Fc2)/3
4673 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.24 e Å3
2 restraintsΔρmin = −0.24 e Å3

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

xyzUiso*/Ueq
O10.47644 (10)0.40995 (8)0.56589 (5)0.0303 (2)
O20.16229 (11)0.56388 (8)0.45303 (5)0.0338 (2)
O1W0.02018 (13)0.44707 (13)0.32908 (8)0.0618 (4)
H10.0749 (19)0.4689 (17)0.3660 (9)0.072 (7)*
H20.065 (2)0.4105 (16)0.2961 (10)0.075 (7)*
N10.27924 (13)0.18848 (9)0.59919 (6)0.0300 (3)
N20.25416 (14)0.11731 (11)0.65838 (7)0.0400 (3)
N30.15632 (15)0.16314 (12)0.69916 (8)0.0440 (3)
N40.45766 (11)0.57194 (9)0.63391 (6)0.0257 (2)
N50.22860 (12)0.68505 (9)0.54874 (7)0.0303 (3)
C10.31772 (15)0.11347 (11)0.46609 (8)0.0293 (3)
C20.39626 (18)0.11496 (14)0.39956 (10)0.0438 (4)
H2A0.48770.14560.40260.053*
C30.3431 (2)0.07249 (16)0.32909 (10)0.0550 (5)
H30.39810.07400.28420.066*
C40.2105 (2)0.02797 (15)0.32374 (10)0.0480 (4)
H40.1741−0.00140.27540.058*
C50.13109 (17)0.02632 (13)0.38883 (9)0.0396 (4)
H50.0396−0.00410.38530.047*
C60.18408 (16)0.06887 (12)0.45964 (9)0.0341 (3)
H60.12830.06750.50420.041*
C70.38193 (15)0.15738 (12)0.54260 (9)0.0343 (3)
H7A0.44420.09930.56610.041*
H7B0.43980.22360.53160.041*
C80.19589 (14)0.28012 (11)0.60124 (8)0.0270 (3)
C90.11891 (17)0.26208 (14)0.66575 (9)0.0376 (3)
H90.05000.31140.68420.045*
C100.19235 (14)0.37276 (11)0.54245 (7)0.0262 (3)
H10A0.09540.38250.52140.031*
H10B0.25030.35150.49830.031*
C110.40317 (13)0.48442 (10)0.59142 (7)0.0237 (3)
C120.24519 (13)0.48458 (11)0.57649 (7)0.0238 (3)
H120.19990.49830.62720.029*
C130.20750 (13)0.58015 (11)0.52044 (8)0.0260 (3)
C140.26507 (14)0.70923 (11)0.62872 (8)0.0285 (3)
C150.19149 (16)0.79278 (12)0.66644 (10)0.0406 (4)
H150.11320.82670.64010.049*
C160.23055 (17)0.82671 (13)0.74123 (10)0.0458 (4)
H160.18060.88470.76570.055*
C170.34254 (18)0.77633 (14)0.78060 (9)0.0429 (4)
H170.37070.80050.83190.052*
C180.41355 (16)0.69081 (12)0.74538 (8)0.0342 (3)
H180.48890.65510.77330.041*
C190.37605 (14)0.65595 (11)0.66908 (7)0.0262 (3)
C200.60870 (14)0.57233 (12)0.65173 (9)0.0326 (3)
H20A0.65580.53100.61100.049*
H20B0.62850.53660.70260.049*
H20C0.64270.64970.65350.049*
C210.19423 (18)0.77880 (13)0.49550 (10)0.0433 (4)
H21A0.21980.75930.44230.065*
H21B0.24610.84550.51310.065*
H21C0.09390.79400.49570.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0280 (5)0.0271 (5)0.0357 (5)0.0058 (4)0.0003 (4)−0.0025 (4)
O20.0347 (6)0.0368 (6)0.0290 (5)0.0067 (4)−0.0072 (4)−0.0011 (4)
O1W0.0327 (7)0.0899 (11)0.0629 (8)−0.0016 (7)0.0039 (6)−0.0415 (8)
N10.0340 (7)0.0267 (6)0.0289 (6)0.0004 (5)−0.0036 (5)0.0020 (5)
N20.0487 (8)0.0347 (7)0.0357 (6)−0.0049 (6)−0.0073 (6)0.0083 (6)
N30.0497 (9)0.0464 (8)0.0356 (7)−0.0104 (7)−0.0001 (6)0.0081 (6)
N40.0225 (6)0.0286 (6)0.0257 (5)0.0015 (4)−0.0009 (4)−0.0022 (5)
N50.0319 (6)0.0249 (6)0.0336 (6)0.0048 (5)−0.0035 (5)0.0013 (5)
C10.0335 (8)0.0185 (6)0.0359 (7)0.0047 (5)0.0022 (6)0.0012 (5)
C20.0440 (10)0.0384 (9)0.0498 (9)−0.0047 (7)0.0128 (7)−0.0010 (7)
C30.0680 (13)0.0574 (11)0.0410 (9)−0.0038 (9)0.0197 (9)−0.0051 (8)
C40.0634 (12)0.0453 (10)0.0348 (8)0.0042 (8)−0.0030 (8)−0.0043 (7)
C50.0391 (9)0.0356 (8)0.0434 (8)0.0008 (7)−0.0051 (7)−0.0024 (7)
C60.0359 (8)0.0315 (7)0.0352 (7)0.0013 (6)0.0034 (6)0.0009 (6)
C70.0305 (8)0.0281 (7)0.0440 (8)0.0059 (6)−0.0021 (6)−0.0030 (6)
C80.0267 (7)0.0259 (7)0.0281 (6)−0.0022 (5)−0.0019 (5)−0.0035 (5)
C90.0380 (8)0.0407 (8)0.0343 (7)−0.0040 (7)0.0036 (6)0.0006 (7)
C100.0256 (7)0.0259 (6)0.0267 (6)0.0005 (5)−0.0019 (5)−0.0018 (5)
C110.0265 (7)0.0238 (6)0.0206 (6)0.0020 (5)−0.0001 (5)0.0026 (5)
C120.0230 (6)0.0252 (6)0.0233 (6)0.0024 (5)0.0005 (5)−0.0012 (5)
C130.0209 (6)0.0279 (7)0.0291 (6)0.0043 (5)0.0001 (5)−0.0008 (5)
C140.0276 (7)0.0232 (6)0.0350 (7)−0.0022 (5)0.0027 (5)−0.0035 (5)
C150.0317 (8)0.0308 (8)0.0592 (10)0.0033 (6)0.0016 (7)−0.0127 (7)
C160.0397 (9)0.0375 (9)0.0612 (10)−0.0042 (7)0.0145 (8)−0.0241 (8)
C170.0465 (10)0.0447 (9)0.0382 (8)−0.0120 (8)0.0092 (7)−0.0174 (7)
C180.0367 (8)0.0355 (8)0.0303 (7)−0.0053 (6)0.0009 (6)−0.0045 (6)
C190.0262 (7)0.0250 (6)0.0278 (6)−0.0028 (5)0.0049 (5)−0.0032 (5)
C200.0246 (7)0.0345 (8)0.0384 (7)0.0003 (6)−0.0031 (6)−0.0033 (6)
C210.0497 (10)0.0293 (8)0.0497 (9)0.0043 (7)−0.0098 (7)0.0087 (7)

Geometric parameters (Å, °)

O1—C111.2263 (15)C7—H7A0.9900
O2—C131.2283 (15)C7—H7B0.9900
O1W—H10.85 (1)C8—C91.371 (2)
O1W—H20.85 (1)C8—C101.4942 (18)
N1—N21.3511 (16)C9—H90.9500
N1—C81.3576 (17)C10—C121.5346 (18)
N1—C71.4591 (19)C10—H10A0.9900
N2—N31.314 (2)C10—H10B0.9900
N3—C91.354 (2)C11—C121.5269 (18)
N4—C111.3642 (16)C12—C131.5237 (18)
N4—C191.4227 (17)C12—H121.0000
N4—C201.4685 (17)C14—C151.3968 (19)
N5—C131.3556 (17)C14—C191.3970 (19)
N5—C141.4252 (17)C15—C161.377 (2)
N5—C211.4714 (18)C15—H150.9500
C1—C61.389 (2)C16—C171.381 (3)
C1—C21.392 (2)C16—H160.9500
C1—C71.5142 (19)C17—C181.381 (2)
C2—C31.383 (2)C17—H170.9500
C2—H2A0.9500C18—C191.4006 (18)
C3—C41.379 (3)C18—H180.9500
C3—H30.9500C20—H20A0.9800
C4—C51.376 (2)C20—H20B0.9800
C4—H40.9500C20—H20C0.9800
C5—C61.388 (2)C21—H21A0.9800
C5—H50.9500C21—H21B0.9800
C6—H60.9500C21—H21C0.9800
H1—O1W—H2110 (2)C8—C10—H10B109.0
N2—N1—C8111.33 (12)C12—C10—H10B109.0
N2—N1—C7118.92 (12)H10A—C10—H10B107.8
C8—N1—C7129.70 (12)O1—C11—N4122.22 (12)
N3—N2—N1106.85 (12)O1—C11—C12121.50 (11)
N2—N3—C9108.83 (12)N4—C11—C12116.28 (11)
C11—N4—C19124.08 (11)C13—C12—C11108.21 (10)
C11—N4—C20117.69 (11)C13—C12—C10110.43 (10)
C19—N4—C20117.86 (11)C11—C12—C10111.81 (10)
C13—N5—C14123.78 (11)C13—C12—H12108.8
C13—N5—C21117.24 (11)C11—C12—H12108.8
C14—N5—C21118.51 (11)C10—C12—H12108.8
C6—C1—C2118.15 (14)O2—C13—N5121.46 (12)
C6—C1—C7122.74 (13)O2—C13—C12122.34 (12)
C2—C1—C7119.09 (13)N5—C13—C12116.19 (11)
C3—C2—C1120.93 (16)C15—C14—C19119.22 (13)
C3—C2—H2A119.5C15—C14—N5118.65 (13)
C1—C2—H2A119.5C19—C14—N5122.05 (12)
C4—C3—C2120.21 (16)C16—C15—C14121.08 (15)
C4—C3—H3119.9C16—C15—H15119.5
C2—C3—H3119.9C14—C15—H15119.5
C5—C4—C3119.64 (16)C15—C16—C17119.87 (14)
C5—C4—H4120.2C15—C16—H16120.1
C3—C4—H4120.2C17—C16—H16120.1
C4—C5—C6120.30 (16)C16—C17—C18119.93 (14)
C4—C5—H5119.8C16—C17—H17120.0
C6—C5—H5119.8C18—C17—H17120.0
C5—C6—C1120.76 (14)C17—C18—C19120.94 (14)
C5—C6—H6119.6C17—C18—H18119.5
C1—C6—H6119.6C19—C18—H18119.5
N1—C7—C1113.52 (12)C14—C19—C18118.89 (13)
N1—C7—H7A108.9C14—C19—N4122.37 (11)
C1—C7—H7A108.9C18—C19—N4118.64 (12)
N1—C7—H7B108.9N4—C20—H20A109.5
C1—C7—H7B108.9N4—C20—H20B109.5
H7A—C7—H7B107.7H20A—C20—H20B109.5
N1—C8—C9103.48 (12)N4—C20—H20C109.5
N1—C8—C10125.18 (12)H20A—C20—H20C109.5
C9—C8—C10131.30 (13)H20B—C20—H20C109.5
N3—C9—C8109.50 (14)N5—C21—H21A109.5
N3—C9—H9125.2N5—C21—H21B109.5
C8—C9—H9125.2H21A—C21—H21B109.5
C8—C10—C12113.14 (10)N5—C21—H21C109.5
C8—C10—H10A109.0H21A—C21—H21C109.5
C12—C10—H10A109.0H21B—C21—H21C109.5
C8—N1—N2—N3−0.75 (15)N4—C11—C12—C10−169.06 (10)
C7—N1—N2—N3−178.41 (12)C8—C10—C12—C13−166.63 (11)
N1—N2—N3—C90.48 (16)C8—C10—C12—C1172.82 (14)
C6—C1—C2—C3−0.4 (2)C14—N5—C13—O2172.36 (12)
C7—C1—C2—C3178.00 (15)C21—N5—C13—O20.4 (2)
C1—C2—C3—C40.1 (3)C14—N5—C13—C12−8.58 (19)
C2—C3—C4—C50.2 (3)C21—N5—C13—C12179.44 (12)
C3—C4—C5—C6−0.2 (3)C11—C12—C13—O2111.69 (14)
C4—C5—C6—C1−0.1 (2)C10—C12—C13—O2−10.99 (18)
C2—C1—C6—C50.5 (2)C11—C12—C13—N5−67.36 (14)
C7—C1—C6—C5−177.93 (13)C10—C12—C13—N5169.96 (11)
N2—N1—C7—C1101.20 (14)C13—N5—C14—C15−132.02 (15)
C8—N1—C7—C1−75.96 (18)C21—N5—C14—C1539.86 (19)
C6—C1—C7—N1−22.18 (19)C13—N5—C14—C1951.2 (2)
C2—C1—C7—N1159.45 (13)C21—N5—C14—C19−136.95 (14)
N2—N1—C8—C90.69 (15)C19—C14—C15—C162.9 (2)
C7—N1—C8—C9178.03 (13)N5—C14—C15—C16−173.96 (14)
N2—N1—C8—C10−177.24 (12)C14—C15—C16—C17−1.2 (3)
C7—N1—C8—C100.1 (2)C15—C16—C17—C18−1.1 (2)
N2—N3—C9—C8−0.06 (17)C16—C17—C18—C191.7 (2)
N1—C8—C9—N3−0.38 (16)C15—C14—C19—C18−2.3 (2)
C10—C8—C9—N3177.37 (13)N5—C14—C19—C18174.49 (12)
N1—C8—C10—C12−113.56 (14)C15—C14—C19—N4−178.56 (13)
C9—C8—C10—C1269.12 (19)N5—C14—C19—N4−1.8 (2)
C19—N4—C11—O1−175.58 (12)C17—C18—C19—C140.0 (2)
C20—N4—C11—O1−2.71 (18)C17—C18—C19—N4176.42 (13)
C19—N4—C11—C125.01 (17)C11—N4—C19—C14−46.74 (18)
C20—N4—C11—C12177.88 (11)C20—N4—C19—C14140.41 (13)
O1—C11—C12—C13−110.30 (13)C11—N4—C19—C18137.00 (13)
N4—C11—C12—C1369.11 (14)C20—N4—C19—C18−35.85 (17)
O1—C11—C12—C1011.53 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1···O20.85 (1)2.02 (1)2.836 (2)161 (2)
O1W—H2···N3i0.85 (1)2.10 (1)2.937 (2)170 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5193).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dardouri, R., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o632. [PMC free article] [PubMed]
  • 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