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

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ISSN: 2056-9890

4,4′-Di­ethyl-2,2′-[(N-cyclo­hexyl­imino)­bis­­(methyl­ene)]diphenol

aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand, bDepartment of Materials and Metallurgical Engineering, Faculty of Engineering, Rajamangala University of Technology Thanyaburi, Pathumthani 12110, Thailand, and cDepartment of Materials Engineering, Faculty of Engineering and Center of Advanced Studies in Industrial Technology, Kasetsart University, Bangkok 10900, Thailand
*Correspondence e-mail: fscinmk@ku.ac.th

(Received 7 September 2012; accepted 24 September 2012; online 29 September 2012)

The title compound, C24H33NO2, exhibits an intra­molecular hydrogen bond between a phenol –OH group and the N atom. In the crystal, mol­ecules are connected by pairs of O—H⋯O hydrogen bonds.

Related literature

For details of the synthesis of N,N-bis­(2-hy­droxy­benz­yl)alkyl­amines, see: Laobuthee et al. (2003[Laobuthee, A., Ishida, H. & Chirachanchai, S. (2003). J. Incl. Phenom. Macro. 47, 179-185.]). For their metal-responsive properties, see: Veranitisagul et al. (2011[Veranitisagul, C., Kaewvilai, A., Sangngern, S., Wattanathana, W., Suramitr, S., Koonsaeng, N. & Laobuthee, A. (2011). Int. J. Mol. Sci. 12, 4365-4377.]). For their use in the synthesis of macrocyclic mol­ecules, see: Rungsimanon et al. (2008[Rungsimanon, T., Laobuthee, A., Miyata, M. & Chirachanchai, S. (2008). J. Incl. Phenom. Macro. 62, 333-338.]).

[Scheme 1]

Experimental

Crystal data
  • C24H33NO2

  • Mr = 367.51

  • Triclinic, [P \overline 1]

  • a = 9.4224 (12) Å

  • b = 10.3799 (16) Å

  • c = 11.8143 (18) Å

  • α = 82.140 (4)°

  • β = 73.960 (4)°

  • γ = 81.676 (4)°

  • V = 1093.1 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.90 × 0.44 × 0.24 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 8721 measured reflections

  • 5350 independent reflections

  • 3648 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.185

  • S = 1.12

  • 5350 reflections

  • 252 parameters

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2 0.94 (3) 2.52 (2) 3.156 (2) 124.8 (18)
O1—H1⋯N 0.94 (3) 1.79 (3) 2.6352 (19) 147.8 (19)
O2—H2⋯O1i 0.88 (3) 1.84 (3) 2.708 (2) 168 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Related literature top

For details of the synthesis of N,N-bis(2-hydroxybenzyl)alkylamines, see: Laobuthee et al. (2003). For their metal-responsive properties, see: Veranitisagul et al. (2011). For their use in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Experimental top

The preparation of the title compound was reported elsewhere (Laobuthee et al., 2003). Colorless blocks were recrystallized from 2-propanol solution.

Refinement top

All H atoms of the compound were placed in the calculated positions with C—H = 0.96 Å and included in the final cycles of refinement in a rigiding model, Uiso(H) = 1.2 Ueq(H). Except H atom of O atoms were located in different fourier map and restrained to their hosts.

Structure description top

For details of the synthesis of N,N-bis(2-hydroxybenzyl)alkylamines, see: Laobuthee et al. (2003). For their metal-responsive properties, see: Veranitisagul et al. (2011). For their use in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms).
4,4'-Diethyl-2,2'-[(N-cyclohexylimino)bis(methylene)]diphenol top
Crystal data top
C24H33NO2Z = 2
Mr = 367.51F(000) = 400.0
Triclinic, P1Dx = 1.117 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4224 (12) ÅCell parameters from 3314 reflections
b = 10.3799 (16) Åθ = 2.6–28.2°
c = 11.8143 (18) ŵ = 0.07 mm1
α = 82.140 (4)°T = 296 K
β = 73.960 (4)°Block, colourless
γ = 81.676 (4)°0.90 × 0.44 × 0.24 mm
V = 1093.1 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
3648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.2°, θmin = 1.8°
φ and ω scansh = 1212
8721 measured reflectionsk = 1313
5350 independent reflectionsl = 1515
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.085P)2 + 0.1411P]
where P = (Fo2 + 2Fc2)/3
5350 reflections(Δ/σ)max < 0.001
252 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C24H33NO2γ = 81.676 (4)°
Mr = 367.51V = 1093.1 (3) Å3
Triclinic, P1Z = 2
a = 9.4224 (12) ÅMo Kα radiation
b = 10.3799 (16) ŵ = 0.07 mm1
c = 11.8143 (18) ÅT = 296 K
α = 82.140 (4)°0.90 × 0.44 × 0.24 mm
β = 73.960 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
3648 reflections with I > 2σ(I)
8721 measured reflectionsRint = 0.022
5350 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.27 e Å3
5350 reflectionsΔρmin = 0.23 e Å3
252 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.15859 (13)0.23370 (12)0.54691 (10)0.0404 (3)
O10.42889 (14)0.18278 (12)0.57669 (13)0.0633 (4)
O20.32304 (15)0.01044 (13)0.44034 (11)0.0627 (4)
C60.29872 (16)0.39939 (15)0.58608 (13)0.0436 (3)
C80.09657 (17)0.19375 (17)0.45693 (14)0.0487 (4)
H8A0.01890.26060.44170.058*
H8B0.05200.11320.48750.058*
C90.21273 (17)0.17318 (17)0.34271 (14)0.0479 (4)
C190.06585 (15)0.21269 (15)0.67028 (13)0.0432 (3)
H19A0.11570.24860.71960.052*
C50.2872 (2)0.52251 (17)0.62205 (16)0.0560 (4)
H5A0.21200.58520.60640.067*
C10.41114 (16)0.30665 (16)0.61073 (14)0.0468 (4)
C20.50701 (18)0.3377 (2)0.67020 (17)0.0594 (5)
H2A0.58130.27500.68720.071*
C140.32556 (18)0.06974 (17)0.33839 (15)0.0509 (4)
C100.2111 (2)0.2556 (2)0.23952 (16)0.0619 (5)
H10A0.13570.32460.24190.074*
C130.4330 (2)0.0513 (2)0.23316 (17)0.0639 (5)
H13A0.50900.01710.23030.077*
C40.3830 (2)0.55644 (19)0.68038 (17)0.0634 (5)
C30.4923 (2)0.4615 (2)0.70427 (17)0.0634 (5)
H3A0.55740.48160.74420.076*
C120.4272 (2)0.1345 (2)0.13275 (18)0.0745 (6)
H12A0.49920.12000.06250.089*
C110.3180 (3)0.2386 (2)0.13297 (17)0.0729 (6)
C200.0648 (3)0.0674 (2)0.71237 (18)0.0735 (6)
H20A0.16610.02530.69760.088*
H20B0.01300.02730.66830.088*
C240.0908 (2)0.2822 (3)0.69530 (19)0.0811 (7)
H24A0.14680.24830.65050.097*
H24B0.08780.37500.67080.097*
C210.0116 (3)0.0471 (2)0.8443 (2)0.0883 (7)
H21A0.01570.04570.86840.106*
H21B0.04600.07940.88870.106*
C150.3654 (3)0.6929 (2)0.7176 (3)0.0950 (8)
H15A0.46010.71050.72630.114*
H15B0.34090.75530.65500.114*
C230.1674 (2)0.2610 (3)0.8282 (2)0.0953 (9)
H23A0.11710.30320.87190.114*
H23B0.26940.30150.84280.114*
C170.3115 (4)0.3322 (3)0.0225 (2)0.1067 (9)
H17A0.28220.42050.04530.128*
H17B0.41020.33020.03120.128*
C220.1661 (3)0.1168 (3)0.8725 (2)0.0993 (9)
H22A0.20870.10740.95750.119*
H22B0.22720.07690.83620.119*
C160.2541 (4)0.7143 (3)0.8259 (3)0.1463 (15)
H16A0.25000.80270.84320.219*
H16B0.27850.65480.88920.219*
H16C0.15920.69980.81780.219*
C180.2088 (4)0.3018 (5)0.0399 (3)0.1597 (18)
H18A0.21070.36370.10830.240*
H18B0.11000.30640.01180.240*
H18C0.23790.21510.06410.240*
C70.20041 (18)0.36794 (15)0.51474 (15)0.0490 (4)
H7A0.11100.42950.52720.059*
H7B0.25200.37830.43130.059*
H10.347 (3)0.176 (2)0.548 (2)0.107 (9)*
H20.398 (3)0.073 (3)0.430 (2)0.095 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0376 (6)0.0464 (7)0.0397 (6)0.0025 (5)0.0143 (5)0.0062 (5)
O10.0465 (6)0.0623 (8)0.0889 (10)0.0105 (5)0.0289 (6)0.0287 (7)
O20.0614 (8)0.0638 (8)0.0573 (8)0.0116 (6)0.0139 (6)0.0103 (6)
C60.0435 (8)0.0465 (8)0.0403 (8)0.0091 (6)0.0092 (6)0.0023 (6)
C80.0416 (8)0.0629 (10)0.0467 (8)0.0035 (7)0.0193 (6)0.0096 (7)
C90.0465 (8)0.0600 (10)0.0430 (8)0.0093 (7)0.0169 (7)0.0105 (7)
C190.0360 (7)0.0535 (9)0.0419 (8)0.0032 (6)0.0117 (6)0.0092 (6)
C50.0613 (10)0.0481 (9)0.0579 (10)0.0094 (8)0.0136 (8)0.0038 (8)
C10.0371 (7)0.0554 (9)0.0481 (9)0.0062 (6)0.0086 (6)0.0098 (7)
C20.0418 (8)0.0740 (12)0.0662 (11)0.0100 (8)0.0165 (8)0.0117 (9)
C140.0499 (9)0.0589 (10)0.0484 (9)0.0097 (7)0.0137 (7)0.0156 (7)
C100.0668 (11)0.0746 (12)0.0518 (10)0.0144 (9)0.0263 (9)0.0028 (9)
C130.0523 (10)0.0784 (13)0.0632 (12)0.0129 (9)0.0055 (8)0.0291 (10)
C40.0730 (12)0.0642 (11)0.0548 (10)0.0314 (10)0.0042 (9)0.0128 (8)
C30.0548 (10)0.0844 (14)0.0581 (11)0.0291 (10)0.0136 (8)0.0114 (9)
C120.0691 (12)0.1093 (18)0.0493 (11)0.0365 (12)0.0006 (9)0.0245 (11)
C110.0801 (14)0.1002 (16)0.0462 (10)0.0369 (12)0.0178 (9)0.0033 (10)
C200.0908 (15)0.0628 (12)0.0577 (11)0.0216 (10)0.0021 (10)0.0050 (9)
C240.0465 (10)0.128 (2)0.0611 (12)0.0191 (11)0.0117 (9)0.0200 (12)
C210.1108 (19)0.0852 (16)0.0598 (13)0.0401 (14)0.0038 (12)0.0003 (11)
C150.122 (2)0.0749 (15)0.0982 (18)0.0377 (14)0.0226 (16)0.0284 (13)
C230.0506 (11)0.163 (3)0.0645 (13)0.0154 (14)0.0041 (9)0.0361 (16)
C170.130 (2)0.145 (3)0.0532 (13)0.0617 (19)0.0274 (14)0.0172 (14)
C220.0791 (16)0.167 (3)0.0577 (13)0.0605 (17)0.0003 (11)0.0198 (15)
C160.151 (3)0.111 (2)0.162 (3)0.030 (2)0.020 (3)0.077 (2)
C180.156 (3)0.253 (5)0.091 (2)0.105 (3)0.064 (2)0.063 (3)
C70.0528 (9)0.0464 (9)0.0505 (9)0.0030 (7)0.0218 (7)0.0001 (7)
Geometric parameters (Å, º) top
N—C71.474 (2)C12—C111.380 (3)
N—C81.4756 (19)C12—H12A0.9300
N—C191.4833 (19)C11—C171.527 (3)
O1—C11.373 (2)C20—C211.525 (3)
O1—H10.94 (3)C20—H20A0.9700
O2—C141.364 (2)C20—H20B0.9700
O2—H20.88 (3)C24—C231.536 (3)
C6—C51.381 (2)C24—H24A0.9700
C6—C11.390 (2)C24—H24B0.9700
C6—C71.506 (2)C21—C221.498 (4)
C8—C91.503 (2)C21—H21A0.9700
C8—H8A0.9700C21—H21B0.9700
C8—H8B0.9700C15—C161.433 (4)
C9—C101.393 (2)C15—H15A0.9700
C9—C141.393 (2)C15—H15B0.9700
C19—C241.515 (2)C23—C221.516 (4)
C19—C201.522 (2)C23—H23A0.9700
C19—H19A0.9800C23—H23B0.9700
C5—C41.384 (3)C17—C181.458 (4)
C5—H5A0.9300C17—H17A0.9700
C1—C21.382 (2)C17—H17B0.9700
C2—C31.375 (3)C22—H22A0.9700
C2—H2A0.9300C22—H22B0.9700
C14—C131.386 (2)C16—H16A0.9600
C10—C111.393 (3)C16—H16B0.9600
C10—H10A0.9300C16—H16C0.9600
C13—C121.377 (3)C18—H18A0.9600
C13—H13A0.9300C18—H18B0.9600
C4—C31.379 (3)C18—H18C0.9600
C4—C151.514 (3)C7—H7A0.9700
C3—H3A0.9300C7—H7B0.9700
C7—N—C8111.05 (12)C21—C20—H20B109.5
C7—N—C19112.92 (12)H20A—C20—H20B108.1
C8—N—C19114.48 (11)C19—C24—C23109.84 (17)
C1—O1—H1106.7 (16)C19—C24—H24A109.7
C14—O2—H2111.5 (16)C23—C24—H24A109.7
C5—C6—C1117.94 (15)C19—C24—H24B109.7
C5—C6—C7121.62 (15)C23—C24—H24B109.7
C1—C6—C7120.30 (14)H24A—C24—H24B108.2
N—C8—C9112.25 (12)C22—C21—C20111.5 (2)
N—C8—H8A109.2C22—C21—H21A109.3
C9—C8—H8A109.2C20—C21—H21A109.3
N—C8—H8B109.2C22—C21—H21B109.3
C9—C8—H8B109.2C20—C21—H21B109.3
H8A—C8—H8B107.9H21A—C21—H21B108.0
C10—C9—C14118.44 (16)C16—C15—C4114.7 (2)
C10—C9—C8121.57 (16)C16—C15—H15A108.6
C14—C9—C8119.99 (15)C4—C15—H15A108.6
N—C19—C24116.08 (14)C16—C15—H15B108.6
N—C19—C20111.12 (13)C4—C15—H15B108.6
C24—C19—C20110.84 (17)H15A—C15—H15B107.6
N—C19—H19A106.0C22—C23—C24111.7 (2)
C24—C19—H19A106.0C22—C23—H23A109.3
C20—C19—H19A106.0C24—C23—H23A109.3
C6—C5—C4122.68 (17)C22—C23—H23B109.3
C6—C5—H5A118.7C24—C23—H23B109.3
C4—C5—H5A118.7H23A—C23—H23B107.9
O1—C1—C2118.84 (15)C18—C17—C11113.9 (2)
O1—C1—C6120.72 (14)C18—C17—H17A108.8
C2—C1—C6120.44 (16)C11—C17—H17A108.8
C3—C2—C1119.93 (18)C18—C17—H17B108.8
C3—C2—H2A120.0C11—C17—H17B108.8
C1—C2—H2A120.0H17A—C17—H17B107.7
O2—C14—C13122.99 (17)C21—C22—C23111.59 (18)
O2—C14—C9117.11 (15)C21—C22—H22A109.3
C13—C14—C9119.90 (17)C23—C22—H22A109.3
C11—C10—C9122.5 (2)C21—C22—H22B109.3
C11—C10—H10A118.8C23—C22—H22B109.3
C9—C10—H10A118.8H22A—C22—H22B108.0
C12—C13—C14119.99 (19)C15—C16—H16A109.5
C12—C13—H13A120.0C15—C16—H16B109.5
C14—C13—H13A120.0H16A—C16—H16B109.5
C3—C4—C5117.73 (17)C15—C16—H16C109.5
C3—C4—C15121.8 (2)H16A—C16—H16C109.5
C5—C4—C15120.5 (2)H16B—C16—H16C109.5
C4—C3—C2121.27 (17)C17—C18—H18A109.5
C4—C3—H3A119.4C17—C18—H18B109.5
C2—C3—H3A119.4H18A—C18—H18B109.5
C11—C12—C13122.14 (18)C17—C18—H18C109.5
C11—C12—H12A118.9H18A—C18—H18C109.5
C13—C12—H12A118.9H18B—C18—H18C109.5
C12—C11—C10117.07 (19)N—C7—C6112.32 (12)
C12—C11—C17122.6 (2)N—C7—H7A109.1
C10—C11—C17120.4 (2)C6—C7—H7A109.1
C19—C20—C21110.63 (17)N—C7—H7B109.1
C19—C20—H20A109.5C6—C7—H7B109.1
C21—C20—H20A109.5H7A—C7—H7B107.9
C19—C20—H20B109.5
C7—N—C8—C970.20 (17)C6—C5—C4—C15179.91 (18)
C19—N—C8—C9160.49 (13)C5—C4—C3—C20.7 (3)
N—C8—C9—C10112.40 (16)C15—C4—C3—C2179.84 (19)
N—C8—C9—C1467.57 (19)C1—C2—C3—C40.1 (3)
C7—N—C19—C2469.65 (18)C14—C13—C12—C111.0 (3)
C8—N—C19—C2458.74 (19)C13—C12—C11—C101.0 (3)
C7—N—C19—C20162.49 (14)C13—C12—C11—C17179.35 (19)
C8—N—C19—C2069.13 (18)C9—C10—C11—C120.6 (3)
C1—C6—C5—C40.4 (2)C9—C10—C11—C17179.71 (18)
C7—C6—C5—C4175.33 (16)N—C19—C20—C21171.75 (17)
C5—C6—C1—O1179.63 (15)C24—C19—C20—C2157.6 (2)
C7—C6—C1—O13.9 (2)N—C19—C24—C23174.90 (18)
C5—C6—C1—C20.5 (2)C20—C19—C24—C2357.1 (2)
C7—C6—C1—C2176.22 (15)C19—C20—C21—C2256.1 (3)
O1—C1—C2—C3179.41 (16)C3—C4—C15—C1697.6 (3)
C6—C1—C2—C30.7 (3)C5—C4—C15—C1681.5 (3)
C10—C9—C14—O2179.05 (14)C19—C24—C23—C2255.7 (3)
C8—C9—C14—O21.0 (2)C12—C11—C17—C1897.7 (3)
C10—C9—C14—C130.3 (2)C10—C11—C17—C1881.9 (4)
C8—C9—C14—C13179.66 (14)C20—C21—C22—C2354.7 (3)
C14—C9—C10—C110.3 (3)C24—C23—C22—C2154.8 (3)
C8—C9—C10—C11179.68 (16)C8—N—C7—C6165.28 (12)
O2—C14—C13—C12178.65 (16)C19—N—C7—C664.58 (16)
C9—C14—C13—C120.7 (3)C5—C6—C7—N143.79 (15)
C6—C5—C4—C31.0 (3)C1—C6—C7—N40.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.94 (3)2.52 (2)3.156 (2)124.8 (18)
O1—H1···N0.94 (3)1.79 (3)2.6352 (19)147.8 (19)
O2—H2···O1i0.88 (3)1.84 (3)2.708 (2)168 (3)
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC24H33NO2
Mr367.51
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.4224 (12), 10.3799 (16), 11.8143 (18)
α, β, γ (°)82.140 (4), 73.960 (4), 81.676 (4)
V3)1093.1 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.90 × 0.44 × 0.24
Data collection
DiffractometerBruker APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8721, 5350, 3648
Rint0.022
(sin θ/λ)max1)0.665
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.185, 1.12
No. of reflections5350
No. of parameters252
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008 and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.94 (3)2.52 (2)3.156 (2)124.8 (18)
O1—H1···N0.94 (3)1.79 (3)2.6352 (19)147.8 (19)
O2—H2···O1i0.88 (3)1.84 (3)2.708 (2)168 (3)
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Thailand Research Fund, Office of the Higher Education Commission, and Rajamangala University of Technology Thanyaburi (grant No. MRG5480046). The authors would like to thank the Department of Chemistry, Faculty of Science, Kasetsart University, and the Center of Advanced Studies in Industrial Technology, Faculty of Engineering, Kasetsart University for partial support.

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLaobuthee, A., Ishida, H. & Chirachanchai, S. (2003). J. Incl. Phenom. Macro. 47, 179–185.  CrossRef CAS Google Scholar
First citationRungsimanon, T., Laobuthee, A., Miyata, M. & Chirachanchai, S. (2008). J. Incl. Phenom. Macro. 62, 333–338.  Web of Science 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 citationVeranitisagul, C., Kaewvilai, A., Sangngern, S., Wattanathana, W., Suramitr, S., Koonsaeng, N. & Laobuthee, A. (2011). Int. J. Mol. Sci. 12, 4365–4377.  Web of Science CrossRef CAS PubMed Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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