Lysergol monohydrate.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: (7-methyl-4,6,6a,7,8,9-hexa-hydro-indolo[4,3,2-fg]quinoline-9-yl)methanol monohydrate], C(16)H(18)N(2)O·H(2)O, 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 mol-ecules contribute to the formation of layers parallel to (10[Formula: see text]).

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 = 272.34

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.052

S = 0.79

1569 reflections

188 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.10 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002632/fj2506sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812002632/fj2506Isup4.mol

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18N2O·H2O	F(000) = 584
Mr = 272.34	Dx = 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

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

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(Fo2) + (0.0045P)2] where P = (Fo2 + 2Fc2)/3
1569 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.10 e Å−3
2 restraints	Δρmin = −0.10 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O1iv	0.84 (3)	1.96 (2)	2.777 (3)	167 (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⋯O1iv	0.84 (3)	1.96 (2)	2.777 (3)	167 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .