organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 Route de Narbonne, Toulouse, France, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 8 February 2010; accepted 9 February 2010; online 13 February 2010)

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[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.]). 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[Dardouri, R., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o632.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21N5O2·H2O

  • Mr = 393.44

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1⋯O2 0.85 (1) 2.02 (1) 2.836 (2) 161 (2)
O1W—H2⋯N3i 0.85 (1) 2.10 (1) 2.937 (2) 170 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C21H21N5O2.H2O at the 70% probability level; hydrogen atoms are drawn as arbitrary radius.
3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)methyl]-1,5-dimethyl- 1,5-benzodiazepine-2,4-dione monohydrate top
Crystal data top
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 top
Bruker APEXII
diffractometer
3454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
ϕ and ω scansh = 1212
34134 measured reflectionsk = 1515
4673 independent reflectionsl = 2222
Refinement top
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 = 1.02 w = 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
Crystal data top
C21H21N5O2·H2OV = 1958.19 (4) Å3
Mr = 393.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6002 (1) ŵ = 0.09 mm1
b = 11.9497 (2) ÅT = 193 K
c = 17.0860 (2) Å0.30 × 0.25 × 0.20 mm
β = 92.527 (1)°
Data collection top
Bruker APEXII
diffractometer
3454 reflections with I > 2σ(I)
34134 measured reflectionsRint = 0.040
4673 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0402 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å3
4673 reflectionsΔρmin = 0.24 e Å3
272 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H40.17410.00140.27540.058*
C50.13109 (17)0.02632 (13)0.38883 (9)0.0396 (4)
H50.03960.00410.38530.047*
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) top
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, º) top
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—N30.75 (15)N4—C11—C12—C10169.06 (10)
C7—N1—N2—N3178.41 (12)C8—C10—C12—C13166.63 (11)
N1—N2—N3—C90.48 (16)C8—C10—C12—C1172.82 (14)
C6—C1—C2—C30.4 (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—C128.58 (19)
C2—C3—C4—C50.2 (3)C21—N5—C13—C12179.44 (12)
C3—C4—C5—C60.2 (3)C11—C12—C13—O2111.69 (14)
C4—C5—C6—C10.1 (2)C10—C12—C13—O210.99 (18)
C2—C1—C6—C50.5 (2)C11—C12—C13—N567.36 (14)
C7—C1—C6—C5177.93 (13)C10—C12—C13—N5169.96 (11)
N2—N1—C7—C1101.20 (14)C13—N5—C14—C15132.02 (15)
C8—N1—C7—C175.96 (18)C21—N5—C14—C1539.86 (19)
C6—C1—C7—N122.18 (19)C13—N5—C14—C1951.2 (2)
C2—C1—C7—N1159.45 (13)C21—N5—C14—C19136.95 (14)
N2—N1—C8—C90.69 (15)C19—C14—C15—C162.9 (2)
C7—N1—C8—C9178.03 (13)N5—C14—C15—C16173.96 (14)
N2—N1—C8—C10177.24 (12)C14—C15—C16—C171.2 (3)
C7—N1—C8—C100.1 (2)C15—C16—C17—C181.1 (2)
N2—N3—C9—C80.06 (17)C16—C17—C18—C191.7 (2)
N1—C8—C9—N30.38 (16)C15—C14—C19—C182.3 (2)
C10—C8—C9—N3177.37 (13)N5—C14—C19—C18174.49 (12)
N1—C8—C10—C12113.56 (14)C15—C14—C19—N4178.56 (13)
C9—C8—C10—C1269.12 (19)N5—C14—C19—N41.8 (2)
C19—N4—C11—O1175.58 (12)C17—C18—C19—C140.0 (2)
C20—N4—C11—O12.71 (18)C17—C18—C19—N4176.42 (13)
C19—N4—C11—C125.01 (17)C11—N4—C19—C1446.74 (18)
C20—N4—C11—C12177.88 (11)C20—N4—C19—C14140.41 (13)
O1—C11—C12—C13110.30 (13)C11—N4—C19—C18137.00 (13)
N4—C11—C12—C1369.11 (14)C20—N4—C19—C1835.85 (17)
O1—C11—C12—C1011.53 (16)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC21H21N5O2·H2O
Mr393.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)9.6002 (1), 11.9497 (2), 17.0860 (2)
β (°) 92.527 (1)
V3)1958.19 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
34134, 4673, 3454
Rint0.040
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.108, 1.02
No. of reflections4673
No. of parameters272
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
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 code: (i) x, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDardouri, R., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMondieig, 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.  CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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