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ISSN: 2056-9890

2-{[(2-Hy­dr­oxy-3,5-di­methyl­benz­yl)(meth­yl)amino]­meth­yl}-4,6-di­methyl­phenol

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

(Received 11 May 2012; accepted 16 May 2012; online 19 May 2012)

In the title compound, C19H25NO2, the dihedral angle between the benzene rings is 53.15 (8)°. One of the –OH groups forms an intra­molecular O—H⋯N link, generating an S(6) ring. The other –OH group forms an inter­molecular O—H⋯N hydrogen bond in the crystal, generating centrosymmetric R22(20) loops.

Related literature

For the synthesis, see: Chirachanchai et al. (2009[Chirachanchai, S., Laobuthee, A. & Phongtamrag, S. (2009). J. Heterocycl. Chem. 46, 714-721.]). For metal-responsive properties of N,N-bis­(2-hy­droxy­benz­yl)alkyl­amines, 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 the use of N,N-bis­(2-hy­droxy­benz­yl)alkyl­amines in the synthesis of macrocyclic mol­ecules, see: Rungsimanon et al. (2008[Rungsimanon, T., Laobuthee, A., Miyata, M. & Chirachanchai, S. (2008). J. Incl. Phenom. Macrocycl. Chem. 62, 333-338.]).

[Scheme 1]

Experimental

Crystal data
  • C19H25NO2

  • Mr = 299.40

  • Triclinic, [P \overline 1]

  • a = 5.4598 (4) Å

  • b = 12.3285 (12) Å

  • c = 13.0441 (13) Å

  • α = 95.412 (3)°

  • β = 96.482 (2)°

  • γ = 94.238 (2)°

  • V = 865.33 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.52 × 0.30 × 0.24 mm

Data collection
  • Siemens P4 diffractometer

  • 6613 measured reflections

  • 3944 independent reflections

  • 2722 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.182

  • S = 1.06

  • 3944 reflections

  • 299 parameters

  • All H-atom parameters refined

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H′⋯N 1.03 (3) 1.71 (3) 2.6895 (18) 156 (2)
O2—H′′⋯O1i 0.94 (3) 2.02 (4) 2.9114 (18) 158 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: XSCANS (Siemens, 1992[Siemens (1992). XSCANS User's Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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.

Supporting information


Related literature top

For the synthesis, see: Chirachanchai et al. (2009). For metal-responsive properties of N,N-bis(2-hydroxybenzyl)alkylamines, see: Veranitisagul et al. (2011). For the use of N,N-bis(2-hydroxybenzyl)alkylamines in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Experimental top

The preparation of the title compound was reported elsewhere (Chirachanchai et al., 2009). Colorless blocks were recrystallized from 2-propanol solution.

Refinement top

All H atoms were located in difference maps and freely refined.

Computing details top

Data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS (Siemens, 1992); data reduction: XSCANS (Siemens, 1992); 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The packing structure of compound (Hydrogen bonds indicated by dash lines).
2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol top
Crystal data top
C19H25NO2Z = 2
Mr = 299.40F(000) = 324
Triclinic, P1Dx = 1.149 Mg m3
a = 5.4598 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3285 (12) ÅCell parameters from 2370 reflections
c = 13.0441 (13) Åθ = 3.2–27.2°
α = 95.412 (3)°µ = 0.07 mm1
β = 96.482 (2)°T = 296 K
γ = 94.238 (2)°Block, colorless
V = 865.33 (14) Å30.52 × 0.30 × 0.24 mm
Data collection top
Siemens P4
diffractometer
2722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.6°, θmin = 1.6°
ω scansh = 67
6613 measured reflectionsk = 1615
3944 independent reflectionsl = 1616
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.1149P)2]
where P = (Fo2 + 2Fc2)/3
3944 reflections(Δ/σ)max < 0.001
299 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C19H25NO2γ = 94.238 (2)°
Mr = 299.40V = 865.33 (14) Å3
Triclinic, P1Z = 2
a = 5.4598 (4) ÅMo Kα radiation
b = 12.3285 (12) ŵ = 0.07 mm1
c = 13.0441 (13) ÅT = 296 K
α = 95.412 (3)°0.52 × 0.30 × 0.24 mm
β = 96.482 (2)°
Data collection top
Siemens P4
diffractometer
2722 reflections with I > 2σ(I)
6613 measured reflectionsRint = 0.021
3944 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.182All H-atom parameters refined
S = 1.06Δρmax = 0.27 e Å3
3944 reflectionsΔρmin = 0.26 e Å3
299 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
O10.5039 (2)0.38818 (10)0.16018 (10)0.0517 (3)
N0.2371 (2)0.21998 (11)0.04228 (10)0.0404 (3)
C10.4085 (3)0.34523 (12)0.24228 (13)0.0427 (4)
C140.4502 (3)0.30149 (13)0.15535 (12)0.0428 (4)
C100.3116 (4)0.11247 (15)0.20468 (13)0.0532 (4)
C20.5258 (3)0.37697 (14)0.34231 (14)0.0479 (4)
C60.1937 (3)0.27292 (13)0.22555 (12)0.0423 (4)
C90.2935 (3)0.20900 (14)0.14369 (12)0.0435 (4)
C30.4254 (3)0.33434 (15)0.42452 (14)0.0529 (4)
C70.0629 (3)0.24498 (16)0.11772 (13)0.0487 (4)
C50.1029 (3)0.23192 (15)0.31059 (14)0.0496 (4)
C130.6237 (3)0.29546 (15)0.22569 (14)0.0490 (4)
C80.1141 (3)0.21588 (16)0.06464 (13)0.0472 (4)
C110.4815 (4)0.10371 (16)0.27587 (14)0.0571 (5)
C40.2141 (3)0.26180 (15)0.41101 (14)0.0529 (4)
C120.6338 (4)0.19581 (17)0.28429 (14)0.0556 (5)
C190.3486 (4)0.11876 (15)0.06030 (16)0.0532 (4)
C160.1053 (6)0.2193 (3)0.50252 (19)0.0796 (7)
C150.7506 (4)0.45821 (19)0.3588 (2)0.0640 (5)
C180.7977 (4)0.3916 (2)0.2386 (2)0.0651 (6)
C170.4954 (9)0.0025 (2)0.3427 (2)0.0933 (9)
O20.4257 (2)0.39465 (10)0.09216 (10)0.0585 (4)
H50.048 (3)0.1827 (16)0.2992 (14)0.052 (5)*
H120.751 (4)0.1965 (19)0.3286 (19)0.079 (7)*
H7B0.068 (4)0.1831 (17)0.1203 (15)0.061 (5)*
H100.205 (4)0.0478 (19)0.1977 (17)0.067 (6)*
H30.510 (4)0.353 (2)0.497 (2)0.083 (7)*
H19C0.222 (4)0.0535 (19)0.0524 (17)0.073 (6)*
H8B0.017 (4)0.1503 (18)0.0811 (16)0.066 (6)*
H8A0.020 (3)0.2867 (16)0.0664 (15)0.056 (5)*
H19B0.430 (4)0.1259 (18)0.1319 (19)0.069 (6)*
H16A0.068 (8)0.216 (4)0.490 (3)0.167 (16)*
H19A0.466 (4)0.1081 (18)0.0130 (17)0.069 (6)*
H18B0.855 (4)0.4335 (17)0.1729 (18)0.059 (6)*
H7A0.030 (4)0.3078 (17)0.0938 (15)0.060 (5)*
H17A0.644 (8)0.001 (4)0.363 (4)0.155 (17)*
H18A0.944 (5)0.369 (2)0.257 (2)0.091 (8)*
H15B0.827 (5)0.459 (2)0.433 (3)0.110 (9)*
H15C0.718 (4)0.535 (2)0.335 (2)0.088 (7)*
H'0.426 (5)0.331 (2)0.100 (2)0.097 (8)*
H16C0.188 (6)0.241 (3)0.565 (3)0.142 (13)*
H18C0.729 (4)0.443 (2)0.276 (2)0.086 (7)*
H''0.483 (5)0.457 (3)0.122 (2)0.104 (9)*
H16B0.079 (7)0.133 (4)0.490 (3)0.139 (12)*
H17C0.424 (9)0.000 (4)0.409 (5)0.184 (18)*
H15A0.879 (5)0.432 (2)0.327 (2)0.086 (8)*
H17B0.490 (6)0.064 (3)0.304 (3)0.136 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0599 (7)0.0452 (7)0.0506 (7)0.0098 (5)0.0196 (6)0.0038 (5)
N0.0436 (7)0.0421 (7)0.0366 (7)0.0005 (5)0.0092 (5)0.0067 (5)
C10.0477 (8)0.0374 (8)0.0446 (9)0.0025 (6)0.0148 (7)0.0026 (6)
C140.0455 (8)0.0447 (9)0.0392 (8)0.0025 (6)0.0059 (6)0.0098 (7)
C100.0697 (11)0.0510 (10)0.0369 (9)0.0053 (9)0.0038 (8)0.0053 (7)
C20.0483 (8)0.0428 (9)0.0521 (10)0.0064 (7)0.0093 (7)0.0029 (7)
C60.0434 (8)0.0437 (9)0.0415 (9)0.0027 (6)0.0124 (6)0.0056 (7)
C90.0477 (8)0.0474 (9)0.0355 (8)0.0013 (7)0.0050 (6)0.0089 (6)
C30.0585 (10)0.0568 (11)0.0435 (10)0.0127 (8)0.0054 (8)0.0006 (8)
C70.0412 (8)0.0608 (11)0.0445 (9)0.0020 (8)0.0112 (7)0.0062 (8)
C50.0514 (9)0.0518 (10)0.0479 (10)0.0001 (7)0.0159 (8)0.0083 (8)
C130.0454 (8)0.0567 (10)0.0489 (9)0.0067 (7)0.0072 (7)0.0216 (8)
C80.0453 (8)0.0563 (10)0.0392 (9)0.0056 (8)0.0053 (7)0.0081 (7)
C110.0812 (12)0.0549 (11)0.0375 (9)0.0118 (9)0.0101 (8)0.0082 (8)
C40.0618 (10)0.0563 (10)0.0444 (10)0.0097 (8)0.0168 (8)0.0096 (8)
C120.0653 (11)0.0656 (12)0.0429 (10)0.0187 (9)0.0186 (8)0.0174 (8)
C190.0667 (11)0.0461 (10)0.0479 (10)0.0079 (8)0.0072 (9)0.0075 (8)
C160.0953 (18)0.100 (2)0.0474 (12)0.0027 (15)0.0207 (12)0.0215 (12)
C150.0553 (11)0.0583 (13)0.0727 (14)0.0043 (9)0.0034 (10)0.0104 (10)
C180.0531 (11)0.0650 (13)0.0848 (17)0.0039 (10)0.0231 (11)0.0303 (13)
C170.160 (3)0.0665 (16)0.0577 (15)0.0170 (17)0.0367 (17)0.0026 (12)
O20.0753 (8)0.0424 (7)0.0598 (8)0.0029 (6)0.0221 (6)0.0052 (6)
Geometric parameters (Å, º) top
O1—C11.3750 (19)C13—C121.393 (3)
O1—H'1.04 (3)C13—C181.498 (3)
N—C191.456 (2)C8—H8B1.03 (2)
N—C71.472 (2)C8—H8A1.05 (2)
N—C81.473 (2)C11—C121.378 (3)
C1—C21.394 (2)C11—C171.515 (3)
C1—C61.403 (2)C4—C161.511 (3)
C14—O21.373 (2)C12—H120.91 (2)
C14—C131.392 (2)C19—H19C1.01 (2)
C14—C91.405 (2)C19—H19B0.98 (2)
C10—C91.384 (2)C19—H19A0.94 (2)
C10—C111.387 (3)C16—H16A0.94 (4)
C10—H100.97 (2)C16—H16C0.89 (4)
C2—C31.387 (3)C16—H16B1.05 (4)
C2—C151.508 (3)C15—H15B1.01 (3)
C6—C51.387 (2)C15—H15C1.05 (3)
C6—C71.501 (2)C15—H15A0.92 (3)
C9—C81.501 (2)C18—H18B0.96 (2)
C3—C41.391 (3)C18—H18A0.92 (3)
C3—H31.00 (3)C18—H18C0.91 (3)
C7—H7B1.01 (2)C17—H17A0.88 (4)
C7—H7A1.01 (2)C17—H17C0.91 (6)
C5—C41.384 (3)C17—H17B0.96 (4)
C5—H50.973 (18)O2—H''0.95 (3)
C1—O1—H'100.4 (15)H8B—C8—H8A107.3 (15)
C19—N—C7111.00 (14)C12—C11—C10117.31 (17)
C19—N—C8111.41 (14)C12—C11—C17121.5 (2)
C7—N—C8110.75 (12)C10—C11—C17121.2 (2)
O1—C1—C2118.74 (14)C5—C4—C3117.52 (16)
O1—C1—C6120.42 (15)C5—C4—C16121.06 (19)
C2—C1—C6120.82 (14)C3—C4—C16121.40 (19)
O2—C14—C13123.18 (14)C11—C12—C13123.26 (16)
O2—C14—C9116.30 (14)C11—C12—H12122.7 (15)
C13—C14—C9120.50 (16)C13—C12—H12114.1 (15)
C9—C10—C11122.18 (17)N—C19—H19C112.4 (12)
C9—C10—H10120.0 (13)N—C19—H19B108.3 (13)
C11—C10—H10117.8 (13)H19C—C19—H19B107.1 (18)
C3—C2—C1118.13 (15)N—C19—H19A108.2 (13)
C3—C2—C15121.91 (17)H19C—C19—H19A110.3 (18)
C1—C2—C15119.93 (17)H19B—C19—H19A110.5 (18)
C5—C6—C1118.57 (15)C4—C16—H16A109 (3)
C5—C6—C7121.62 (14)C4—C16—H16C116 (2)
C1—C6—C7119.77 (14)H16A—C16—H16C123 (3)
C10—C9—C14118.83 (15)C4—C16—H16B109 (2)
C10—C9—C8121.39 (15)H16A—C16—H16B84 (3)
C14—C9—C8119.77 (15)H16C—C16—H16B111 (3)
C2—C3—C4122.74 (17)C2—C15—H15B107.5 (17)
C2—C3—H3119.9 (13)C2—C15—H15C114.4 (13)
C4—C3—H3117.3 (13)H15B—C15—H15C116 (2)
N—C7—C6111.73 (13)C2—C15—H15A111.8 (16)
N—C7—H7B113.6 (11)H15B—C15—H15A98 (2)
C6—C7—H7B107.5 (12)H15C—C15—H15A109 (2)
N—C7—H7A107.2 (11)C13—C18—H18B111.5 (12)
C6—C7—H7A111.3 (11)C13—C18—H18A110.3 (17)
H7B—C7—H7A105.5 (16)H18B—C18—H18A101 (2)
C4—C5—C6122.20 (16)C13—C18—H18C114.8 (15)
C4—C5—H5119.1 (11)H18B—C18—H18C102 (2)
C6—C5—H5118.7 (11)H18A—C18—H18C116 (2)
C14—C13—C12117.91 (15)C11—C17—H17A107 (3)
C14—C13—C18122.03 (18)C11—C17—H17C111 (3)
C12—C13—C18120.06 (17)H17A—C17—H17C91 (3)
N—C8—C9112.46 (12)C11—C17—H17B112 (2)
N—C8—H8B110.9 (11)H17A—C17—H17B104 (4)
C9—C8—H8B108.7 (11)H17C—C17—H17B127 (4)
N—C8—H8A105.3 (11)C14—O2—H''110.3 (18)
C9—C8—H8A112.1 (10)
O1—C1—C2—C3179.02 (15)C1—C6—C5—C41.4 (3)
C6—C1—C2—C30.6 (2)C7—C6—C5—C4176.34 (16)
O1—C1—C2—C150.9 (2)O2—C14—C13—C12178.87 (15)
C6—C1—C2—C15177.59 (17)C9—C14—C13—C120.8 (2)
O1—C1—C6—C5179.66 (14)O2—C14—C13—C180.5 (3)
C2—C1—C6—C51.2 (2)C9—C14—C13—C18178.61 (17)
O1—C1—C6—C71.9 (2)C19—N—C8—C965.34 (18)
C2—C1—C6—C7176.55 (15)C7—N—C8—C9170.58 (14)
C11—C10—C9—C140.9 (3)C10—C9—C8—N105.66 (17)
C11—C10—C9—C8177.98 (17)C14—C9—C8—N73.2 (2)
O2—C14—C9—C10179.40 (15)C9—C10—C11—C120.2 (3)
C13—C14—C9—C101.2 (2)C9—C10—C11—C17179.2 (2)
O2—C14—C9—C80.5 (2)C6—C5—C4—C30.9 (3)
C13—C14—C9—C8177.70 (14)C6—C5—C4—C16177.5 (2)
C1—C2—C3—C40.0 (3)C2—C3—C4—C50.2 (3)
C15—C2—C3—C4178.09 (18)C2—C3—C4—C16178.2 (2)
C19—N—C7—C667.71 (18)C10—C11—C12—C130.3 (3)
C8—N—C7—C6167.98 (14)C17—C11—C12—C13178.8 (2)
C5—C6—C7—N136.72 (16)C14—C13—C12—C110.0 (3)
C1—C6—C7—N45.6 (2)C18—C13—C12—C11179.35 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H···N1.03 (3)1.71 (3)2.6895 (18)156 (2)
O2—H···O1i0.94 (3)2.02 (4)2.9114 (18)158 (2)
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC19H25NO2
Mr299.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)5.4598 (4), 12.3285 (12), 13.0441 (13)
α, β, γ (°)95.412 (3), 96.482 (2), 94.238 (2)
V3)865.33 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.52 × 0.30 × 0.24
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6613, 3944, 2722
Rint0.021
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.182, 1.06
No. of reflections3944
No. of parameters299
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.27, 0.26

Computer programs: XSCANS (Siemens, 1992), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H'···N1.03 (3)1.71 (3)2.6895 (18)156 (2)
O2—H''···O1i0.94 (3)2.02 (4)2.9114 (18)158 (2)
Symmetry code: (i) x+1, y+1, z.
 

Acknowledgements

This work was supported by the Thailand Research Fund (grant No. MRG5480046). The authors would like to thank the Department of Chemistry, Faculty of Science, Kasetsart University for partial support.

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