Lysergol monohydrate

Merkel, S.; Köppen, R.; Koch, M.; Emmerling, F.; Nehls, I.

doi:10.1107/S1600536812002632

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o523

doi:10.1107/S1600536812002632

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Lysergol monohydrate

Stefan Merkel,^a Robert Köppen,^a Matthias Koch,^a Franziska Emmerling ^a ^* and Irene Nehls ^a

^aBAM Federal Institute for Materials Research and Testing, Department Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin-Adlershof, Germany
^*Correspondence e-mail: franziska.emmerling@bam.de

(Received 11 January 2012; accepted 20 January 2012; online 25 January 2012)

In the title compound [systematic name: (7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate], C₁₆H₁₈N₂O·H₂O, the non-aromatic ring (ring C of the ergoline skeleton) directly fused to the aromatic rings is nearly planar, with a maximum deviation of 0.659 (3) Å, and shows an envelope conformation. In the crystal, hydrogen bonds between the lysergol and water molecules contribute to the formation of layers parallel to (10 $[\overline{2}]$ ).

Related literature

For the natural occurrence of lysergol, see: Amor-Prats & Harborne (1993 ); Uhlig et al. (2007 ). For the crystal structures of other alkaloids produced by Clavicipitaceae see: Pakhomova et al. (1995 ); Merkel et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₈N₂O·H₂O
M_r = 272.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6234 (12) Å
b = 12.3803 (19) Å
c = 15.877 (2) Å
V = 1498.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.2 × 0.1 × 0.08 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.85, T_max = 0.96
12705 measured reflections
1569 independent reflections
747 reflections with I > 2σ(I)
R_int = 0.122

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.052
S = 0.79
1569 reflections
188 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	2.03	2.845 (3)	176
N2—H2A⋯O2ⁱⁱ	0.86	2.17	2.896 (4)	142
O2—H17⋯N1ⁱⁱⁱ	0.84 (3)	2.00 (3)	2.826 (3)	171 (3)
O2—H18⋯O1^iv	0.84 (3)	1.96 (2)	2.777 (3)	167 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812002632/fj2506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002632/fj2506Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812002632/fj2506Isup4.mol

checkCIF report

Comment top

Lysergol is a clavine alkaloid produced by fungi of the family Clavicipitaceae. It naturally occurs in sclerotia and can be isolated from seeds of some species of the genus Ipomoea (Amor-Prats et al., 1993). Lysergol has an ergoline skeleton and is therefore structurally related to ergot alkaloids like ergometrinine (Merkel et al., 2010) or ergotamine (Pakhomova et al., 1995).

The molecule crytsallizes in the orthorhombic space group P2₁2₁2₁. The molecular structure of the compound and the atom-labeling scheme are shown in Fig 1.

The absolute configuration could not be defined confidently based on the single-crystal diffraction data. It was however established based on liquid chromatography data that confirmed the epimeric purity of the obtained lysergol crystals. Each lysergol molecule forms four hydrogen bonds to four adjacent water molecules. As a consequence, each water molecule is involved in four hydrogen bonds to four lysergol molecules, resulting in a three dimentional framework structure.

Related literature top

For the natural occurrence of lysergol, see: Amor-Prats & Harborne (1993); Uhlig et al. (2007). For the crystal structures of other alkaloids produced by Clavicipitaceae see: Pakhomova et al. (1995); Merkel et al. (2010).

Experimental top

1.4 mg of epimeric pure lysergol (purity > 97%, HPLC-FLD), obtained from Sigma-Aldrich (Taufkirchen, Germany), were dissolved in a glass vial in 1.2 ml of a 84:16 (v:v) acetonitril:water solution. The vial was subsequently capped and stored in the dark at ambient temperature (approximately 23 °C) until crystal formation was complete (2 days). To avoid any epimerization of lysergol to isolysergol the epimeric purity of the resulted crystals was proofed by HPLC-FLD.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : ORTEP representation of the title compound with atomic labeling shown with 30% probability displacement ellipsoids.
	Fig. 2. : View of the unit cell of the title compound along [100], showing the hydrogen bonds between the lysergol and adjacent water molecules. Hydrogen bonds are drawn as dashed green lines.

(7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate top

Crystal data top

C₁₆H₁₈N₂O·H₂O	F(000) = 584
M_r = 272.34	D_x = 1.207 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 46 reflections
a = 7.6234 (12) Å	θ = 4–22°
b = 12.3803 (19) Å	µ = 0.08 mm⁻¹
c = 15.877 (2) Å	T = 296 K
V = 1498.5 (4) Å³	Needle, colourless
Z = 4	0.2 × 0.1 × 0.08 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	1569 independent reflections
Radiation source: fine-focus sealed tube	747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.122
ω/2θ scans	θ_max = 25.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
T_min = 0.85, T_max = 0.96	k = −13→14
12705 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	w = 1/[σ²(F_o²) + (0.0045P)²] where P = (F_o² + 2F_c²)/3
1569 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.10 e Å⁻³
2 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O·H₂O	V = 1498.5 (4) Å³
M_r = 272.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6234 (12) Å	µ = 0.08 mm⁻¹
b = 12.3803 (19) Å	T = 296 K
c = 15.877 (2) Å	0.2 × 0.1 × 0.08 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	1569 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	747 reflections with I > 2σ(I)
T_min = 0.85, T_max = 0.96	R_int = 0.122
12705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	2 restraints
wR(F²) = 0.052	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	Δρ_max = 0.10 e Å⁻³
1569 reflections	Δρ_min = −0.10 e Å⁻³
188 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
O1	0.3895 (3)	1.17847 (16)	0.55746 (12)	0.0635 (7)
H1	0.4465	1.2344	0.5538	0.095*
N1	0.9193 (3)	0.95002 (18)	0.53144 (15)	0.0442 (7)
N2	0.8345 (5)	0.6912 (2)	0.21044 (17)	0.0648 (9)
H2A	0.8399	0.6452	0.1699	0.078*
C1	0.4962 (4)	1.0956 (2)	0.5939 (2)	0.0562 (9)
H1A	0.4266	1.0305	0.6000	0.067*
H1B	0.5326	1.1182	0.6497	0.067*
C2	0.6602 (4)	1.0695 (2)	0.5413 (2)	0.0477 (8)
H11	0.7270	1.1362	0.5326	0.057*
C3	0.7769 (4)	0.9876 (2)	0.5872 (2)	0.0521 (10)
H3A	0.8269	1.0210	0.6371	0.062*
H3B	0.7067	0.9264	0.6051	0.062*
C4	0.8463 (4)	0.8815 (2)	0.46293 (19)	0.0442 (8)
H4	0.8020	0.8151	0.4889	0.053*
C5	0.9912 (4)	0.8488 (2)	0.3992 (2)	0.0571 (10)
H5A	1.0518	0.9129	0.3795	0.068*
H5B	1.0762	0.8025	0.4268	0.068*
C6	0.9116 (5)	0.7897 (3)	0.3247 (2)	0.0488 (9)
C7	0.9690 (5)	0.7142 (3)	0.2684 (2)	0.0627 (11)
H7	1.0799	0.6828	0.2684	0.075*
C8	0.6916 (6)	0.7556 (3)	0.2301 (2)	0.0541 (10)
C9	0.7374 (4)	0.8162 (3)	0.30186 (19)	0.0458 (9)
C10	0.6234 (5)	0.8872 (3)	0.34156 (19)	0.0457 (9)
C11	0.6897 (4)	0.9386 (3)	0.42089 (19)	0.0435 (9)
C12	0.6124 (4)	1.0234 (2)	0.4570 (2)	0.0514 (9)
H12	0.5216	1.0566	0.4276	0.062*
C13	0.4597 (4)	0.9014 (3)	0.30490 (19)	0.0596 (10)
H13	0.3807	0.9500	0.3284	0.072*
C14	0.4120 (5)	0.8423 (3)	0.2318 (2)	0.0637 (10)
H14	0.3014	0.8530	0.2085	0.076*
C15	0.5253 (6)	0.7691 (3)	0.1937 (2)	0.0678 (12)
H15	0.4922	0.7305	0.1460	0.081*
C16	1.0496 (4)	0.8895 (2)	0.58200 (19)	0.0682 (11)
H16A	0.9984	0.8231	0.6013	0.102*
H16B	1.0844	0.9322	0.6296	0.102*
H16C	1.1504	0.8739	0.5479	0.102*
O2	0.4063 (3)	0.86910 (19)	0.96241 (15)	0.0648 (7)
H17	0.468 (4)	0.918 (2)	0.9836 (19)	0.097*
H18	0.327 (3)	0.847 (3)	0.9945 (17)	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0514 (16)	0.0583 (16)	0.0807 (18)	0.0025 (14)	−0.0038 (13)	−0.0068 (13)
N1	0.0467 (19)	0.0461 (17)	0.0398 (17)	0.0035 (15)	−0.0078 (16)	0.0001 (15)
N2	0.090 (3)	0.050 (2)	0.055 (2)	0.003 (2)	0.005 (2)	−0.0091 (16)
C1	0.055 (3)	0.055 (2)	0.058 (2)	0.004 (2)	0.005 (2)	−0.0022 (19)
C2	0.053 (2)	0.044 (2)	0.046 (2)	0.0011 (18)	0.0011 (19)	0.0009 (19)
C3	0.065 (3)	0.047 (2)	0.044 (2)	−0.003 (2)	−0.001 (2)	−0.0040 (18)
C4	0.047 (2)	0.041 (2)	0.045 (2)	−0.0003 (17)	−0.0002 (19)	0.0014 (19)
C5	0.054 (3)	0.059 (2)	0.058 (2)	0.0101 (19)	−0.001 (2)	−0.0029 (19)
C6	0.059 (3)	0.048 (2)	0.040 (2)	0.005 (2)	0.004 (2)	−0.0014 (18)
C7	0.070 (3)	0.063 (3)	0.055 (2)	0.009 (2)	−0.001 (2)	0.001 (2)
C8	0.065 (3)	0.054 (3)	0.043 (2)	−0.006 (2)	0.001 (2)	−0.001 (2)
C9	0.048 (3)	0.055 (3)	0.034 (2)	−0.006 (2)	−0.005 (2)	0.0015 (19)
C10	0.047 (3)	0.053 (2)	0.038 (2)	−0.006 (2)	−0.0012 (19)	0.0022 (18)
C11	0.044 (2)	0.044 (2)	0.043 (2)	0.0015 (18)	0.0029 (18)	0.0008 (18)
C12	0.053 (2)	0.052 (2)	0.049 (2)	0.0046 (19)	−0.001 (2)	0.0075 (18)
C13	0.056 (3)	0.069 (3)	0.053 (3)	0.000 (2)	−0.007 (2)	−0.005 (2)
C14	0.055 (3)	0.075 (3)	0.061 (3)	−0.008 (3)	−0.013 (2)	−0.002 (2)
C15	0.087 (4)	0.067 (3)	0.049 (3)	−0.016 (3)	−0.001 (3)	−0.003 (2)
C16	0.074 (3)	0.066 (3)	0.065 (2)	0.012 (2)	−0.025 (2)	0.002 (2)
O2	0.071 (2)	0.0660 (18)	0.0570 (16)	−0.0169 (14)	0.0090 (14)	−0.0127 (14)

Geometric parameters (Å, º) top

O1—C1	1.432 (3)	C5—H5B	0.9700
O1—H1	0.8200	C6—C7	1.365 (4)
N1—C3	1.476 (3)	C6—C9	1.415 (4)
N1—C16	1.481 (3)	C7—H7	0.9300
N1—C4	1.487 (3)	C8—C15	1.403 (4)
N2—C8	1.385 (4)	C8—C9	1.408 (4)
N2—C7	1.407 (4)	C9—C10	1.388 (4)
N2—H2A	0.8600	C10—C13	1.388 (4)
C1—C2	1.538 (3)	C10—C11	1.499 (4)
C1—H1A	0.9700	C11—C12	1.333 (3)
C1—H1B	0.9700	C12—H12	0.9300
C2—C12	1.500 (4)	C13—C14	1.420 (4)
C2—C3	1.534 (4)	C13—H13	0.9300
C2—H11	0.9800	C14—C15	1.390 (4)
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—H15	0.9300
C4—C11	1.540 (4)	C16—H16A	0.9600
C4—C5	1.552 (4)	C16—H16B	0.9600
C4—H4	0.9800	C16—H16C	0.9600
C5—C6	1.517 (4)	O2—H17	0.838 (10)
C5—H5A	0.9700	O2—H18	0.837 (10)

C1—O1—H1	109.5	C7—C6—C9	107.0 (3)
C3—N1—C16	109.1 (2)	C7—C6—C5	135.4 (4)
C3—N1—C4	110.1 (2)	C9—C6—C5	117.6 (3)
C16—N1—C4	111.0 (2)	C6—C7—N2	109.4 (3)
C8—N2—C7	108.0 (3)	C6—C7—H7	125.3
C8—N2—H2A	126.0	N2—C7—H7	125.3
C7—N2—H2A	126.0	N2—C8—C15	133.3 (4)
O1—C1—C2	113.1 (3)	N2—C8—C9	107.1 (3)
O1—C1—H1A	109.0	C15—C8—C9	119.6 (4)
C2—C1—H1A	109.0	C10—C9—C8	123.3 (4)
O1—C1—H1B	109.0	C10—C9—C6	128.2 (3)
C2—C1—H1B	109.0	C8—C9—C6	108.4 (3)
H1A—C1—H1B	107.8	C9—C10—C13	116.9 (3)
C12—C2—C3	108.3 (2)	C9—C10—C11	116.1 (3)
C12—C2—C1	111.5 (3)	C13—C10—C11	127.0 (3)
C3—C2—C1	110.6 (3)	C12—C11—C10	123.1 (3)
C12—C2—H11	108.8	C12—C11—C4	121.2 (3)
C3—C2—H11	108.8	C10—C11—C4	115.5 (3)
C1—C2—H11	108.8	C11—C12—C2	125.1 (3)
N1—C3—C2	110.4 (3)	C11—C12—H12	117.4
N1—C3—H3A	109.6	C2—C12—H12	117.4
C2—C3—H3A	109.6	C10—C13—C14	120.5 (3)
N1—C3—H3B	109.6	C10—C13—H13	119.7
C2—C3—H3B	109.6	C14—C13—H13	119.7
H3A—C3—H3B	108.1	C15—C14—C13	122.2 (4)
N1—C4—C11	110.2 (2)	C15—C14—H14	118.9
N1—C4—C5	111.1 (2)	C13—C14—H14	118.9
C11—C4—C5	112.9 (3)	C14—C15—C8	117.4 (4)
N1—C4—H4	107.5	C14—C15—H15	121.3
C11—C4—H4	107.5	C8—C15—H15	121.3
C5—C4—H4	107.5	N1—C16—H16A	109.5
C6—C5—C4	110.5 (3)	N1—C16—H16B	109.5
C6—C5—H5A	109.6	H16A—C16—H16B	109.5
C4—C5—H5A	109.6	N1—C16—H16C	109.5
C6—C5—H5B	109.6	H16A—C16—H16C	109.5
C4—C5—H5B	109.6	H16B—C16—H16C	109.5
H5A—C5—H5B	108.1	H17—O2—H18	114 (3)

O1—C1—C2—C12	−64.4 (3)	C7—C6—C9—C8	−0.4 (4)
O1—C1—C2—C3	175.0 (2)	C5—C6—C9—C8	177.9 (3)
C16—N1—C3—C2	168.4 (2)	C8—C9—C10—C13	−3.2 (5)
C4—N1—C3—C2	−69.5 (3)	C6—C9—C10—C13	178.2 (3)
C12—C2—C3—N1	48.7 (3)	C8—C9—C10—C11	175.5 (3)
C1—C2—C3—N1	171.3 (2)	C6—C9—C10—C11	−3.1 (5)
C3—N1—C4—C11	49.4 (3)	C9—C10—C11—C12	166.3 (3)
C16—N1—C4—C11	170.4 (2)	C13—C10—C11—C12	−15.2 (5)
C3—N1—C4—C5	175.3 (2)	C9—C10—C11—C4	−18.4 (4)
C16—N1—C4—C5	−63.8 (3)	C13—C10—C11—C4	160.1 (3)
N1—C4—C5—C6	−173.7 (2)	N1—C4—C11—C12	−14.6 (4)
C11—C4—C5—C6	−49.3 (3)	C5—C4—C11—C12	−139.5 (3)
C4—C5—C6—C7	−152.8 (4)	N1—C4—C11—C10	170.0 (2)
C4—C5—C6—C9	29.4 (4)	C5—C4—C11—C10	45.1 (4)
C9—C6—C7—N2	−0.5 (4)	C10—C11—C12—C2	172.3 (3)
C5—C6—C7—N2	−178.5 (3)	C4—C11—C12—C2	−2.7 (5)
C8—N2—C7—C6	1.3 (4)	C3—C2—C12—C11	−14.0 (4)
C7—N2—C8—C15	178.3 (4)	C1—C2—C12—C11	−136.0 (3)
C7—N2—C8—C9	−1.5 (4)	C9—C10—C13—C14	2.0 (5)
N2—C8—C9—C10	−177.6 (3)	C11—C10—C13—C14	−176.5 (3)
C15—C8—C9—C10	2.5 (5)	C10—C13—C14—C15	−0.3 (5)
N2—C8—C9—C6	1.2 (4)	C13—C14—C15—C8	−0.4 (5)
C15—C8—C9—C6	−178.6 (3)	N2—C8—C15—C14	179.6 (3)
C7—C6—C9—C10	178.4 (3)	C9—C8—C15—C14	−0.6 (5)
C5—C6—C9—C10	−3.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.03	2.845 (3)	176
N2—H2A···O2ⁱⁱ	0.86	2.17	2.896 (4)	142
O2—H17···N1ⁱⁱⁱ	0.84 (3)	2.00 (3)	2.826 (3)	171 (3)
O2—H18···O1^iv	0.84 (3)	1.96 (2)	2.777 (3)	167 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+3/2, −z+1; (iii) −x+3/2, −y+2, z+1/2; (iv) −x+1/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O·H₂O
M_r	272.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.6234 (12), 12.3803 (19), 15.877 (2)
V (Å³)	1498.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.2 × 0.1 × 0.08

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.85, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	12705, 1569, 747
R_int	0.122
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.052, 0.79
No. of reflections	1569
No. of parameters	188
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.10

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.03	2.845 (3)	176
N2—H2A···O2ⁱⁱ	0.86	2.17	2.896 (4)	142
O2—H17···N1ⁱⁱⁱ	0.84 (3)	2.00 (3)	2.826 (3)	171 (3)
O2—H18···O1^iv	0.84 (3)	1.96 (2)	2.777 (3)	167 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+3/2, −z+1; (iii) −x+3/2, −y+2, z+1/2; (iv) −x+1/2, −y+2, z+1/2.

References

Amor-Prats, D. & Harborne, J. B. (1993). Biochem. Syst. Ecol. 21, 455–462. CAS Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Merkel, S., Köppen, R., Koch, M., Emmerling, F. & Nehls, I. (2010). Acta Cryst. E66, o2275. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pakhomova, S., Ondráucek, J., Huusák, M., Kratochvíl, B., Jegorov, A. & Stuchlík, J. (1995). Acta Cryst. C51, 308–311. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uhlig, S., Vikoren, T., Ivanova, L. & Handeland, K. (2007). Rapid Commun. Mass Spectrom. 21, 1651–1660. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 2| February 2012| Page o523

doi:10.1107/S1600536812002632

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