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

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N′-[(Bi­phenyl-4-yl)methyl­ene]-2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]acetohydrazide

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 23 February 2010; accepted 23 February 2010; online 3 March 2010)

In the title compound, C30H36N2O2S, the dihedral angle between the two aromatic rings of the biphenyl residue is 31.2 (1)°. The two methyl­ene C atoms subtend an angle of 99.9 (1)° at the S atom. In the crystal, mol­ecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds. The hydroxyl group is shielded by the tert-butyl residues and is therefore not involved in any hydrogen bonding.

Related literature

When heated in acidified ethanol the compound gave biphenyl-4-carbaldehyde azine; see: Yehye et al. (2008[Yehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64, o2444.]).

[Scheme 1]

Experimental

Crystal data
  • C30H36N2O2S

  • Mr = 488.67

  • Triclinic, [P \overline 1]

  • a = 9.1104 (11) Å

  • b = 10.5601 (12) Å

  • c = 15.5146 (18) Å

  • α = 104.435 (2)°

  • β = 102.805 (2)°

  • γ = 97.559 (2)°

  • V = 1381.7 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.15 mm−1

  • T = 293 K

  • 0.40 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.944, Tmax = 0.986

  • 10977 measured reflections

  • 4873 independent reflections

  • 3404 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.04

  • 4873 reflections

  • 324 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.87 (1) 1.97 (1) 2.827 (2) 174 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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

When heated in acidified ethanol the compound gave biphenyl-4-carbaldehyde azine; see: Yehye et al. (2008).

Experimental top

2-(3,5-Di-tert-butyl-4-hydroxybenzylthio)acetohydrazine (0.5 g, 1.54 mmol) and 4-phenylbenzaldehyde (0.28 g, 1.54 mmol) were stirred in ethanol (10 ml) for 2 h. The resulting solid was collected and recrystallized from ethanol to give the Schiff base as large prismatic crystals in 90% yield. The formulation was assumed from 1H NMR spectral analysis.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The hydroxy and amino H-atoms were located in a difference Fourier map, and were refined isotropically with distance restraints of O–H 0.84±0.01 Å and N–H 0.86±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 C30H36N2O2S at the the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
N'-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4- hydroxybenzyl)sulfanyl]acetohydrazide top
Crystal data top
C30H36N2O2SZ = 2
Mr = 488.67F(000) = 524
Triclinic, P1Dx = 1.175 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1104 (11) ÅCell parameters from 2001 reflections
b = 10.5601 (12) Åθ = 2.3–21.2°
c = 15.5146 (18) ŵ = 0.15 mm1
α = 104.435 (2)°T = 293 K
β = 102.805 (2)°Prism, colorless
γ = 97.559 (2)°0.40 × 0.10 × 0.10 mm
V = 1381.7 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer
4873 independent reflections
Radiation source: fine-focus sealed tube3404 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.944, Tmax = 0.986k = 1212
10977 measured reflectionsl = 1618
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0664P)2 + 0.0264P]
where P = (Fo2 + 2Fc2)/3
4873 reflections(Δ/σ)max = 0.001
324 parametersΔρmax = 0.17 e Å3
2 restraintsΔρmin = 0.19 e Å3
Crystal data top
C30H36N2O2Sγ = 97.559 (2)°
Mr = 488.67V = 1381.7 (3) Å3
Triclinic, P1Z = 2
a = 9.1104 (11) ÅMo Kα radiation
b = 10.5601 (12) ŵ = 0.15 mm1
c = 15.5146 (18) ÅT = 293 K
α = 104.435 (2)°0.40 × 0.10 × 0.10 mm
β = 102.805 (2)°
Data collection top
Bruker SMART APEX
diffractometer
4873 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3404 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.986Rint = 0.035
10977 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0472 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.17 e Å3
4873 reflectionsΔρmin = 0.19 e Å3
324 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.76556 (7)0.68306 (6)0.78801 (4)0.0490 (2)
O10.5035 (2)0.7947 (2)1.15128 (12)0.0773 (6)
H1O0.414 (2)0.758 (5)1.146 (4)0.20 (2)*
O20.54723 (17)0.65943 (15)0.58105 (10)0.0543 (4)
N10.7059 (2)0.51789 (18)0.55439 (12)0.0445 (5)
H10.6318 (18)0.4645 (17)0.5098 (11)0.048 (6)*
N20.8470 (2)0.48554 (18)0.57906 (12)0.0449 (4)
C10.5274 (2)0.7853 (2)1.06541 (15)0.0472 (6)
C20.4146 (2)0.7092 (2)0.98530 (15)0.0443 (5)
C30.4476 (2)0.7061 (2)0.90205 (15)0.0475 (6)
H30.37560.65560.84770.057*
C40.5832 (2)0.7749 (2)0.89644 (15)0.0465 (6)
C50.6914 (2)0.8472 (2)0.97723 (15)0.0468 (6)
H50.78310.89310.97360.056*
C60.6687 (2)0.8541 (2)1.06363 (15)0.0428 (5)
C70.2608 (2)0.6336 (2)0.98892 (17)0.0538 (6)
C80.2880 (3)0.5279 (3)1.0406 (2)0.0774 (8)
H8A0.34230.46671.01000.116*
H8B0.19100.48011.04090.116*
H8C0.34770.57111.10290.116*
C90.1710 (3)0.7315 (3)1.0355 (2)0.0724 (8)
H9A0.07740.68261.03940.109*
H9B0.14750.79190.99970.109*
H9C0.23230.78111.09640.109*
C100.1580 (3)0.5607 (3)0.8920 (2)0.0779 (8)
H10A0.20750.49530.86120.117*
H10B0.14050.62380.85750.117*
H10C0.06160.51740.89630.117*
C110.7924 (3)0.9341 (2)1.15209 (15)0.0513 (6)
C120.7331 (3)1.0494 (3)1.20689 (19)0.0837 (9)
H12A0.64511.01411.22430.126*
H12B0.70471.10661.16930.126*
H12C0.81241.09951.26130.126*
C130.8421 (3)0.8430 (3)1.21158 (19)0.0748 (8)
H13A0.75560.80541.22920.112*
H13B0.92110.89401.26590.112*
H13C0.88080.77251.17680.112*
C140.9374 (3)0.9949 (3)1.13007 (19)0.0720 (8)
H14A1.01211.04541.18650.108*
H14B0.91151.05251.09240.108*
H14C0.97930.92481.09760.108*
C150.6138 (3)0.7729 (3)0.80454 (16)0.0578 (6)
H15A0.64330.86350.80250.069*
H15B0.52120.73020.75530.069*
C160.7967 (2)0.7190 (2)0.68495 (14)0.0445 (5)
H16A0.79390.81180.68930.053*
H16B0.89690.70360.67860.053*
C170.6743 (2)0.6309 (2)0.60228 (14)0.0415 (5)
C180.8649 (3)0.3747 (2)0.53133 (15)0.0486 (6)
H180.78430.32070.48260.058*
C191.0115 (2)0.3318 (2)0.55261 (15)0.0448 (5)
C201.0305 (3)0.2105 (2)0.50071 (16)0.0520 (6)
H200.95020.15780.45130.062*
C211.1672 (3)0.1671 (2)0.52141 (16)0.0508 (6)
H211.17700.08520.48570.061*
C221.2902 (2)0.2427 (2)0.59426 (15)0.0438 (5)
C231.2704 (3)0.3650 (2)0.64509 (16)0.0539 (6)
H231.35110.41860.69390.065*
C241.1346 (3)0.4084 (2)0.62486 (16)0.0549 (6)
H241.12510.49060.66020.066*
C251.4349 (3)0.1944 (2)0.61918 (15)0.0470 (6)
C261.4334 (3)0.0584 (3)0.60401 (17)0.0578 (6)
H261.34100.00240.57610.069*
C271.5670 (3)0.0121 (3)0.62980 (19)0.0703 (8)
H271.56400.07880.61990.084*
C281.7033 (3)0.1010 (4)0.6700 (2)0.0748 (8)
H281.79320.07030.68750.090*
C291.7081 (3)0.2344 (3)0.68445 (19)0.0719 (8)
H291.80150.29400.71120.086*
C301.5748 (3)0.2822 (3)0.65969 (18)0.0607 (7)
H301.57940.37340.67030.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0509 (4)0.0565 (4)0.0402 (3)0.0122 (3)0.0105 (3)0.0156 (3)
O10.0721 (13)0.1141 (16)0.0468 (11)0.0004 (12)0.0283 (10)0.0237 (10)
O20.0481 (9)0.0556 (10)0.0505 (10)0.0197 (8)0.0053 (7)0.0020 (7)
N10.0409 (11)0.0479 (11)0.0375 (11)0.0131 (9)0.0044 (9)0.0024 (9)
N20.0435 (11)0.0508 (11)0.0427 (11)0.0165 (9)0.0120 (8)0.0135 (9)
C10.0484 (13)0.0578 (14)0.0400 (13)0.0093 (11)0.0186 (11)0.0169 (11)
C20.0395 (12)0.0499 (13)0.0463 (13)0.0104 (10)0.0133 (10)0.0166 (11)
C30.0421 (12)0.0549 (14)0.0426 (13)0.0100 (10)0.0075 (10)0.0119 (11)
C40.0441 (13)0.0619 (15)0.0389 (13)0.0151 (11)0.0156 (10)0.0177 (11)
C50.0415 (12)0.0554 (14)0.0473 (14)0.0050 (10)0.0160 (11)0.0203 (11)
C60.0415 (12)0.0453 (13)0.0432 (13)0.0070 (10)0.0119 (10)0.0158 (10)
C70.0394 (12)0.0612 (15)0.0635 (16)0.0065 (11)0.0167 (11)0.0220 (13)
C80.0623 (17)0.0742 (19)0.111 (2)0.0098 (14)0.0326 (17)0.0471 (18)
C90.0513 (15)0.086 (2)0.090 (2)0.0194 (14)0.0322 (15)0.0283 (16)
C100.0483 (16)0.086 (2)0.084 (2)0.0105 (14)0.0134 (14)0.0132 (16)
C110.0503 (13)0.0509 (14)0.0456 (13)0.0032 (11)0.0079 (11)0.0093 (11)
C120.092 (2)0.077 (2)0.0620 (18)0.0160 (17)0.0096 (16)0.0065 (15)
C130.0641 (17)0.088 (2)0.0652 (18)0.0056 (15)0.0033 (14)0.0320 (16)
C140.0584 (16)0.0727 (18)0.0679 (18)0.0148 (14)0.0045 (13)0.0154 (14)
C150.0559 (15)0.0806 (18)0.0440 (14)0.0211 (13)0.0167 (11)0.0238 (13)
C160.0409 (12)0.0466 (13)0.0419 (13)0.0035 (10)0.0127 (10)0.0067 (10)
C170.0439 (13)0.0447 (13)0.0350 (12)0.0099 (10)0.0108 (10)0.0094 (10)
C180.0481 (13)0.0527 (14)0.0438 (13)0.0136 (11)0.0105 (11)0.0111 (11)
C190.0491 (13)0.0489 (13)0.0411 (13)0.0158 (11)0.0152 (11)0.0151 (11)
C200.0504 (14)0.0530 (14)0.0471 (14)0.0117 (11)0.0086 (11)0.0076 (11)
C210.0560 (15)0.0455 (13)0.0521 (14)0.0184 (11)0.0175 (12)0.0092 (11)
C220.0487 (13)0.0494 (14)0.0409 (12)0.0140 (10)0.0167 (10)0.0202 (11)
C230.0533 (14)0.0534 (15)0.0484 (14)0.0148 (12)0.0020 (11)0.0108 (12)
C240.0650 (16)0.0494 (14)0.0490 (14)0.0222 (12)0.0106 (12)0.0102 (11)
C250.0527 (14)0.0565 (15)0.0424 (13)0.0185 (11)0.0204 (11)0.0223 (11)
C260.0605 (16)0.0606 (16)0.0577 (16)0.0232 (12)0.0166 (12)0.0200 (12)
C270.080 (2)0.0734 (19)0.0688 (18)0.0430 (17)0.0213 (16)0.0245 (15)
C280.0611 (18)0.106 (3)0.0719 (19)0.0418 (18)0.0209 (15)0.0365 (18)
C290.0492 (15)0.096 (2)0.076 (2)0.0150 (15)0.0146 (14)0.0374 (17)
C300.0555 (15)0.0686 (17)0.0667 (17)0.0133 (13)0.0179 (13)0.0326 (14)
Geometric parameters (Å, º) top
S1—C161.804 (2)C12—H12C0.9600
S1—C151.805 (2)C13—H13A0.9600
O1—C11.379 (3)C13—H13B0.9600
O1—H1O0.83 (1)C13—H13C0.9600
O2—C171.230 (2)C14—H14A0.9600
N1—C171.342 (3)C14—H14B0.9600
N1—N21.371 (2)C14—H14C0.9600
N1—H10.87 (1)C15—H15A0.9700
N2—C181.271 (3)C15—H15B0.9700
C1—C21.402 (3)C16—C171.500 (3)
C1—C61.402 (3)C16—H16A0.9700
C2—C31.383 (3)C16—H16B0.9700
C2—C71.539 (3)C18—C191.462 (3)
C3—C41.380 (3)C18—H180.9300
C3—H30.9300C19—C241.386 (3)
C4—C51.379 (3)C19—C201.387 (3)
C4—C151.508 (3)C20—C211.383 (3)
C5—C61.387 (3)C20—H200.9300
C5—H50.9300C21—C221.387 (3)
C6—C111.534 (3)C21—H210.9300
C7—C101.530 (3)C22—C231.392 (3)
C7—C91.540 (3)C22—C251.482 (3)
C7—C81.543 (3)C23—C241.375 (3)
C8—H8A0.9600C23—H230.9300
C8—H8B0.9600C24—H240.9300
C8—H8C0.9600C25—C301.387 (3)
C9—H9A0.9600C25—C261.394 (3)
C9—H9B0.9600C26—C271.385 (3)
C9—H9C0.9600C26—H260.9300
C10—H10A0.9600C27—C281.367 (4)
C10—H10B0.9600C27—H270.9300
C10—H10C0.9600C28—C291.363 (4)
C11—C121.535 (3)C28—H280.9300
C11—C141.536 (3)C29—C301.388 (3)
C11—C131.535 (3)C29—H290.9300
C12—H12A0.9600C30—H300.9300
C12—H12B0.9600
C16—S1—C1599.92 (10)C11—C13—H13C109.5
C1—O1—H1O110 (4)H13A—C13—H13C109.5
C17—N1—N2120.93 (18)H13B—C13—H13C109.5
C17—N1—H1117.2 (14)C11—C14—H14A109.5
N2—N1—H1121.8 (14)C11—C14—H14B109.5
C18—N2—N1116.47 (18)H14A—C14—H14B109.5
O1—C1—C2120.5 (2)C11—C14—H14C109.5
O1—C1—C6116.5 (2)H14A—C14—H14C109.5
C2—C1—C6122.98 (19)H14B—C14—H14C109.5
C3—C2—C1116.67 (19)C4—C15—S1109.84 (15)
C3—C2—C7121.2 (2)C4—C15—H15A109.7
C1—C2—C7122.10 (19)S1—C15—H15A109.7
C4—C3—C2122.6 (2)C4—C15—H15B109.7
C4—C3—H3118.7S1—C15—H15B109.7
C2—C3—H3118.7H15A—C15—H15B108.2
C5—C4—C3118.6 (2)C17—C16—S1109.61 (14)
C5—C4—C15120.1 (2)C17—C16—H16A109.7
C3—C4—C15121.4 (2)S1—C16—H16A109.7
C4—C5—C6122.6 (2)C17—C16—H16B109.7
C4—C5—H5118.7S1—C16—H16B109.7
C6—C5—H5118.7H16A—C16—H16B108.2
C5—C6—C1116.5 (2)O2—C17—N1121.11 (19)
C5—C6—C11121.18 (19)O2—C17—C16120.80 (19)
C1—C6—C11122.28 (19)N1—C17—C16118.04 (19)
C10—C7—C9106.5 (2)N2—C18—C19120.3 (2)
C10—C7—C2111.37 (19)N2—C18—H18119.8
C9—C7—C2110.51 (19)C19—C18—H18119.8
C10—C7—C8107.4 (2)C24—C19—C20117.8 (2)
C9—C7—C8110.5 (2)C24—C19—C18121.9 (2)
C2—C7—C8110.45 (19)C20—C19—C18120.2 (2)
C7—C8—H8A109.5C21—C20—C19120.9 (2)
C7—C8—H8B109.5C21—C20—H20119.5
H8A—C8—H8B109.5C19—C20—H20119.5
C7—C8—H8C109.5C20—C21—C22121.5 (2)
H8A—C8—H8C109.5C20—C21—H21119.3
H8B—C8—H8C109.5C22—C21—H21119.3
C7—C9—H9A109.5C21—C22—C23117.1 (2)
C7—C9—H9B109.5C21—C22—C25121.8 (2)
H9A—C9—H9B109.5C23—C22—C25121.1 (2)
C7—C9—H9C109.5C24—C23—C22121.6 (2)
H9A—C9—H9C109.5C24—C23—H23119.2
H9B—C9—H9C109.5C22—C23—H23119.2
C7—C10—H10A109.5C23—C24—C19121.1 (2)
C7—C10—H10B109.5C23—C24—H24119.5
H10A—C10—H10B109.5C19—C24—H24119.5
C7—C10—H10C109.5C30—C25—C26118.0 (2)
H10A—C10—H10C109.5C30—C25—C22121.5 (2)
H10B—C10—H10C109.5C26—C25—C22120.6 (2)
C12—C11—C14107.5 (2)C27—C26—C25121.2 (3)
C12—C11—C6110.4 (2)C27—C26—H26119.4
C14—C11—C6111.31 (19)C25—C26—H26119.4
C12—C11—C13110.4 (2)C28—C27—C26119.6 (3)
C14—C11—C13106.5 (2)C28—C27—H27120.2
C6—C11—C13110.45 (19)C26—C27—H27120.2
C11—C12—H12A109.5C29—C28—C27120.3 (3)
C11—C12—H12B109.5C29—C28—H28119.8
H12A—C12—H12B109.5C27—C28—H28119.8
C11—C12—H12C109.5C28—C29—C30120.6 (3)
H12A—C12—H12C109.5C28—C29—H29119.7
H12B—C12—H12C109.5C30—C29—H29119.7
C11—C13—H13A109.5C25—C30—C29120.3 (3)
C11—C13—H13B109.5C25—C30—H30119.9
H13A—C13—H13B109.5C29—C30—H30119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.87 (1)1.97 (1)2.827 (2)174 (2)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC30H36N2O2S
Mr488.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.1104 (11), 10.5601 (12), 15.5146 (18)
α, β, γ (°)104.435 (2), 102.805 (2), 97.559 (2)
V3)1381.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.40 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.944, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
10977, 4873, 3404
Rint0.035
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.135, 1.04
No. of reflections4873
No. of parameters324
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N1—H1···O2i0.87 (1)1.97 (1)2.827 (2)174 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

We thank the University of Malaya (grant No. FS338/2008 A) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  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
First citationYehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64, o2444.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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