2-Hydroxy­benzyl alcohol–phenanthroline (1/1)

Ton, C.Q.; Bolte, M.

doi:10.1107/S1600536809044699

organic compounds

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Volume 65| Part 11| November 2009| Page o2936

https://doi.org/10.1107/S1600536809044699

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2-Hydroxybenzyl alcohol–phenanthroline (1/1)

Cuong Quoc Ton ^a and Michael Bolte ^b ^*

^aInstitut für Organische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and ^bInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 20 October 2009; accepted 27 October 2009; online 31 October 2009)

Crystals of the title compound, C₁₂H₈N₂·C₇H₈O₂, were obtained during cocrystallization experiments of a compound with two hydrogen-bond donors (2-hydroxybenzyl alcohol) with another compound containing two hydrogen-bond acceptors (phenanthroline). Unexpectedly, the two molecules do not form dimers with two O—H⋯N hydrogen bonds connecting the two molecules. However, one of the hydroxy groups forms a bifurcated hydrogen bond to both phenanthroline N atoms, whereas the other hydroxy group forms an O—H⋯O hydrogen bond to a symmetry-equivalent 2-hydroxybenzyl alcohol molecule. In addition, the crystal packing is stabilized by π–π interactions between the two phenanthroline ring systems, with a centroid–centroid distance of 3.570 Å.

Related literature

For co-crystallization experiments, see: Ton & Bolte (2005 ); Tutughamiarso et al. (2009 ).

Experimental

Crystal data

C₁₂H₈N₂·C₇H₈O₂
M_r = 304.34
Monoclinic, P 2₁ /n
a = 7.264 (1) Å
b = 20.256 (3) Å
c = 11.082 (2) Å
β = 109.13 (3)°
V = 1540.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.60 × 0.50 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: none
20425 measured reflections
2885 independent reflections
2518 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.099
S = 1.06
2885 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.93	1.69	2.6125 (14)	168
O2—H2O⋯N1ⁱⁱ	0.87	2.29	3.0390 (15)	144
O2—H2O⋯N2ⁱⁱ	0.87	2.15	2.8663 (14)	140
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809044699/om2291sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044699/om2291Isup2.hkl

checkCIF report

Comment top

The aim of our research is the cocrystallization of two small organic compounds in order to examine the hydrogen bonds formed between hydrogen-bond acceptors and hydrogen-bond donors (Ton & Bolte, 2005; Tutughamiarso et al., 2009). In this work, we wanted to cocrystallize phenanthroline and 2-hydroxybenzyl alcohol. However, the cocrystal, we obtained, did not show the expected AA/DD pattern, i.e. with two O—H···N hydrogen bonds connecting the two molecules to a dimer. However, one of the hydroxy groups forms a bifurcated hydrogen bonds to both phenanthroline N atoms, whereas the other hydroxy group forms a O—H···O hydrogen bond to a symmetry equivalent 2-hydroxybenzyl alcohol molecule. In addition, the crystal packing is stabilized by π–π interactions between two phenanthroline ring systems forming a centrosymmetric dimer with a centroid···centroid distance of 3.570 Å. The second molecule is generated by the symmetry operation 1 - x, -y, 1 - z.

Related literature top

For co-crystallization experiments, see: Ton & Bolte (2005); Tutughamiarso et al. (2009).

Experimental top

The complex consisting of 1,10-phenanthroline and 2-hydroxybenzylenealcohol was obtained by to the method of isothermal vaporization. 1,10-phenanthroline and 2-hydroxybenzylenealcohol were added in an equimolar ratio (10 mmol) into a flask. Afterwards chloroform was added dropwise until the substances were completely dissolved. Then, the flask was sealed and set aside at room temperature. After two weeks crystals of the complex were obtained.

Structure description top

For co-crystallization experiments, see: Ton & Bolte (2005); Tutughamiarso et al. (2009).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound viewed along the c axis. Hydrogen atoms bonded to C omitted. Hydrogen bonds shown as dashed lines.

2-Hydroxybenzyl alcohol–phenanthroline (1/1) top

Crystal data top

C₁₂H₈N₂·C₇H₈O₂	F(000) = 640
M_r = 304.34	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11957 reflections
a = 7.264 (1) Å	θ = 3.0–25.0°
b = 20.256 (3) Å	µ = 0.09 mm⁻¹
c = 11.082 (2) Å	T = 173 K
β = 109.13 (3)°	Block, colourless
V = 1540.6 (4) Å³	0.60 × 0.50 × 0.30 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	2518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 25.7°, θ_min = 2.8°
ω scans	h = −8→8
20425 measured reflections	k = −24→24
2885 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0569P)² + 0.2526P] where P = (F_o² + 2F_c²)/3
2885 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₈N₂·C₇H₈O₂	V = 1540.6 (4) Å³
M_r = 304.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.264 (1) Å	µ = 0.09 mm⁻¹
b = 20.256 (3) Å	T = 173 K
c = 11.082 (2) Å	0.60 × 0.50 × 0.30 mm
β = 109.13 (3)°

Data collection top

Stoe IPDS II two-circle diffractometer	2518 reflections with I > 2σ(I)
20425 measured reflections	R_int = 0.036
2885 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
2885 reflections	Δρ_min = −0.21 e Å⁻³
208 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

	x	y	z	U_iso*/U_eq
N1	0.68091 (17)	0.08958 (5)	0.49625 (11)	0.0357 (3)
N2	0.89787 (17)	0.03273 (5)	0.72184 (11)	0.0371 (3)
C1	0.72912 (18)	0.02470 (6)	0.49544 (13)	0.0330 (3)
C2	0.5740 (2)	0.11589 (7)	0.38637 (14)	0.0418 (3)
H2	0.5403	0.1612	0.3860	0.050*
C3	0.5071 (2)	0.08146 (8)	0.27060 (15)	0.0478 (4)
H3	0.4303	0.1029	0.1945	0.057*
C4	0.5553 (2)	0.01591 (8)	0.26982 (15)	0.0477 (4)
H4	0.5114	−0.0087	0.1927	0.057*
C5	0.6694 (2)	−0.01440 (7)	0.38328 (14)	0.0398 (3)
C6	0.7275 (2)	−0.08270 (7)	0.38997 (17)	0.0480 (4)
H6	0.6881	−0.1088	0.3146	0.058*
C7	0.8361 (2)	−0.11014 (7)	0.50050 (18)	0.0497 (4)
H7	0.8733	−0.1552	0.5017	0.060*
C8	0.8973 (2)	−0.07275 (6)	0.61706 (15)	0.0406 (3)
C9	1.0057 (2)	−0.10017 (7)	0.73516 (18)	0.0513 (4)
H9	1.0437	−0.1452	0.7402	0.062*
C10	1.0568 (2)	−0.06217 (8)	0.84299 (18)	0.0526 (4)
H10	1.1285	−0.0803	0.9238	0.063*
C11	1.0001 (2)	0.00436 (7)	0.83078 (15)	0.0459 (4)
H11	1.0376	0.0308	0.9057	0.055*
C12	0.84467 (19)	−0.00511 (6)	0.61498 (13)	0.0342 (3)
O1	0.96385 (12)	0.19916 (5)	0.97867 (8)	0.0343 (2)
H1O	0.9040	0.1823	0.8970	0.051*
O2	1.25869 (12)	0.33737 (4)	1.24759 (8)	0.0299 (2)
H2O	1.2750	0.3699	1.2006	0.045*
C13	1.16077 (16)	0.20302 (6)	1.00360 (11)	0.0254 (3)
C14	1.26346 (16)	0.24552 (6)	1.10244 (11)	0.0252 (3)
C15	1.46410 (17)	0.25043 (6)	1.13083 (12)	0.0300 (3)
H15	1.5363	0.2785	1.1984	0.036*
C16	1.56203 (18)	0.21500 (6)	1.06219 (13)	0.0333 (3)
H16	1.6992	0.2192	1.0829	0.040*
C17	1.45820 (18)	0.17387 (6)	0.96403 (12)	0.0325 (3)
H17	1.5239	0.1501	0.9164	0.039*
C18	1.25733 (18)	0.16711 (6)	0.93473 (12)	0.0293 (3)
H18	1.1863	0.1382	0.8682	0.035*
C19	1.15095 (17)	0.28505 (6)	1.17128 (11)	0.0297 (3)
H19A	1.0333	0.3037	1.1071	0.036*
H19B	1.1069	0.2548	1.2265	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0415 (6)	0.0277 (5)	0.0471 (7)	−0.0037 (5)	0.0269 (5)	−0.0039 (5)
N2	0.0471 (7)	0.0279 (6)	0.0456 (7)	−0.0038 (5)	0.0277 (5)	−0.0007 (5)
C1	0.0352 (7)	0.0267 (6)	0.0486 (8)	−0.0082 (5)	0.0295 (6)	−0.0070 (5)
C2	0.0450 (8)	0.0384 (8)	0.0490 (8)	−0.0024 (6)	0.0248 (7)	0.0022 (6)
C3	0.0454 (8)	0.0580 (10)	0.0469 (8)	−0.0112 (7)	0.0244 (7)	0.0013 (7)
C4	0.0474 (8)	0.0588 (10)	0.0470 (8)	−0.0211 (7)	0.0293 (7)	−0.0152 (7)
C5	0.0415 (7)	0.0374 (7)	0.0552 (9)	−0.0164 (6)	0.0356 (7)	−0.0155 (6)
C6	0.0556 (9)	0.0368 (8)	0.0695 (11)	−0.0192 (7)	0.0449 (9)	−0.0242 (7)
C7	0.0539 (9)	0.0247 (7)	0.0892 (13)	−0.0095 (6)	0.0490 (9)	−0.0169 (7)
C8	0.0388 (7)	0.0240 (6)	0.0719 (10)	−0.0049 (5)	0.0357 (7)	−0.0035 (6)
C9	0.0459 (8)	0.0278 (7)	0.0909 (13)	0.0019 (6)	0.0371 (9)	0.0081 (8)
C10	0.0484 (9)	0.0439 (8)	0.0702 (11)	0.0004 (7)	0.0257 (8)	0.0165 (8)
C11	0.0534 (9)	0.0402 (8)	0.0509 (9)	−0.0057 (6)	0.0263 (7)	0.0027 (6)
C12	0.0365 (7)	0.0250 (6)	0.0538 (8)	−0.0066 (5)	0.0321 (6)	−0.0056 (5)
O1	0.0208 (4)	0.0510 (6)	0.0310 (5)	−0.0017 (4)	0.0083 (3)	−0.0068 (4)
O2	0.0376 (5)	0.0240 (4)	0.0281 (4)	−0.0015 (3)	0.0108 (4)	0.0035 (3)
C13	0.0224 (5)	0.0288 (6)	0.0254 (6)	0.0018 (4)	0.0084 (4)	0.0058 (5)
C14	0.0248 (6)	0.0253 (6)	0.0264 (6)	0.0022 (4)	0.0094 (5)	0.0061 (5)
C15	0.0254 (6)	0.0291 (6)	0.0349 (6)	−0.0022 (5)	0.0090 (5)	0.0024 (5)
C16	0.0232 (6)	0.0341 (7)	0.0446 (7)	0.0017 (5)	0.0138 (5)	0.0059 (6)
C17	0.0323 (6)	0.0325 (6)	0.0380 (7)	0.0079 (5)	0.0188 (5)	0.0061 (5)
C18	0.0304 (6)	0.0299 (6)	0.0283 (6)	0.0024 (5)	0.0105 (5)	0.0016 (5)
C19	0.0263 (6)	0.0326 (6)	0.0311 (6)	−0.0018 (5)	0.0104 (5)	−0.0024 (5)

Geometric parameters (Å, º) top

N1—C2	1.3230 (19)	C10—C11	1.403 (2)
N1—C1	1.3609 (17)	C10—H10	0.9500
N2—C11	1.3235 (19)	C11—H11	0.9500
N2—C12	1.3562 (17)	O1—C13	1.3674 (14)
C1—C5	1.4166 (19)	O1—H1O	0.9310
C1—C12	1.448 (2)	O2—C19	1.4203 (15)
C2—C3	1.400 (2)	O2—H2O	0.8714
C2—H2	0.9500	C13—C18	1.3980 (17)
C3—C4	1.374 (2)	C13—C14	1.4006 (17)
C3—H3	0.9500	C14—C15	1.3901 (17)
C4—C5	1.401 (2)	C14—C19	1.5165 (16)
C4—H4	0.9500	C15—C16	1.3979 (18)
C5—C6	1.441 (2)	C15—H15	0.9500
C6—C7	1.341 (2)	C16—C17	1.3816 (19)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.437 (2)	C17—C18	1.3938 (18)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.402 (2)	C18—H18	0.9500
C8—C12	1.4206 (18)	C19—H19A	0.9900
C9—C10	1.366 (3)	C19—H19B	0.9900
C9—H9	0.9500

C2—N1—C1	117.24 (12)	N2—C11—C10	124.36 (15)
C11—N2—C12	117.73 (12)	N2—C11—H11	117.8
N1—C1—C5	122.70 (13)	C10—C11—H11	117.8
N1—C1—C12	118.04 (12)	N2—C12—C8	122.19 (13)
C5—C1—C12	119.26 (12)	N2—C12—C1	118.51 (11)
N1—C2—C3	124.43 (14)	C8—C12—C1	119.30 (12)
N1—C2—H2	117.8	C13—O1—H1O	110.0
C3—C2—H2	117.8	C19—O2—H2O	111.4
C4—C3—C2	118.34 (15)	O1—C13—C18	122.60 (11)
C4—C3—H3	120.8	O1—C13—C14	116.55 (10)
C2—C3—H3	120.8	C18—C13—C14	120.85 (11)
C3—C4—C5	119.67 (14)	C15—C14—C13	118.11 (11)
C3—C4—H4	120.2	C15—C14—C19	123.11 (11)
C5—C4—H4	120.2	C13—C14—C19	118.77 (10)
C4—C5—C1	117.62 (13)	C14—C15—C16	121.53 (12)
C4—C5—C6	122.97 (14)	C14—C15—H15	119.2
C1—C5—C6	119.42 (15)	C16—C15—H15	119.2
C7—C6—C5	121.31 (14)	C17—C16—C15	119.61 (11)
C7—C6—H6	119.3	C17—C16—H16	120.2
C5—C6—H6	119.3	C15—C16—H16	120.2
C6—C7—C8	121.26 (13)	C16—C17—C18	120.15 (11)
C6—C7—H7	119.4	C16—C17—H17	119.9
C8—C7—H7	119.4	C18—C17—H17	119.9
C9—C8—C12	117.59 (14)	C17—C18—C13	119.73 (12)
C9—C8—C7	122.96 (14)	C17—C18—H18	120.1
C12—C8—C7	119.44 (14)	C13—C18—H18	120.1
C10—C9—C8	120.10 (14)	O2—C19—C14	114.26 (10)
C10—C9—H9	119.9	O2—C19—H19A	108.7
C8—C9—H9	119.9	C14—C19—H19A	108.7
C9—C10—C11	118.03 (16)	O2—C19—H19B	108.7
C9—C10—H10	121.0	C14—C19—H19B	108.7
C11—C10—H10	121.0	H19A—C19—H19B	107.6

C2—N1—C1—C5	−0.08 (18)	C11—N2—C12—C1	178.66 (11)
C2—N1—C1—C12	−179.49 (11)	C9—C8—C12—N2	0.86 (18)
C1—N1—C2—C3	0.4 (2)	C7—C8—C12—N2	179.91 (11)
N1—C2—C3—C4	−0.2 (2)	C9—C8—C12—C1	−178.65 (11)
C2—C3—C4—C5	−0.3 (2)	C7—C8—C12—C1	0.40 (18)
C3—C4—C5—C1	0.55 (19)	N1—C1—C12—N2	0.52 (17)
C3—C4—C5—C6	−179.40 (13)	C5—C1—C12—N2	−178.92 (10)
N1—C1—C5—C4	−0.37 (18)	N1—C1—C12—C8	−179.96 (11)
C12—C1—C5—C4	179.04 (11)	C5—C1—C12—C8	0.61 (17)
N1—C1—C5—C6	179.58 (11)	O1—C13—C14—C15	179.69 (10)
C12—C1—C5—C6	−1.02 (17)	C18—C13—C14—C15	−0.63 (17)
C4—C5—C6—C7	−179.66 (13)	O1—C13—C14—C19	−1.68 (15)
C1—C5—C6—C7	0.40 (19)	C18—C13—C14—C19	178.01 (11)
C5—C6—C7—C8	0.6 (2)	C13—C14—C15—C16	0.95 (17)
C6—C7—C8—C9	177.95 (13)	C19—C14—C15—C16	−177.62 (11)
C6—C7—C8—C12	−1.0 (2)	C14—C15—C16—C17	−0.24 (19)
C12—C8—C9—C10	0.1 (2)	C15—C16—C17—C18	−0.81 (18)
C7—C8—C9—C10	−178.94 (13)	C16—C17—C18—C13	1.12 (18)
C8—C9—C10—C11	−0.9 (2)	O1—C13—C18—C17	179.27 (11)
C12—N2—C11—C10	−0.1 (2)	C14—C13—C18—C17	−0.39 (17)
C9—C10—C11—N2	1.0 (2)	C15—C14—C19—O2	12.73 (16)
C11—N2—C12—C8	−0.86 (18)	C13—C14—C19—O2	−165.84 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.93	1.69	2.6125 (14)	168
O2—H2O···N1ⁱⁱ	0.87	2.29	3.0390 (15)	144
O2—H2O···N2ⁱⁱ	0.87	2.15	2.8663 (14)	140

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈N₂·C₇H₈O₂
M_r	304.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.264 (1), 20.256 (3), 11.082 (2)
β (°)	109.13 (3)
V (Å³)	1540.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.50 × 0.30

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20425, 2885, 2518
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.099, 1.06
No. of reflections	2885
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.93	1.69	2.6125 (14)	168.4
O2—H2O···N1ⁱⁱ	0.87	2.29	3.0390 (15)	143.7
O2—H2O···N2ⁱⁱ	0.87	2.15	2.8663 (14)	139.7

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2.

References

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406–o1407. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Tutughamiarso, M., Bolte, M. & Egert, E. (2009). Acta Cryst. C65, o574–o578. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page o2936

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