N-Methyl-isosalsoline from Hammada scoparia.

THE TITLE COMPOUND (SYSTEMATIC NAME: 1,2-dimethyl-6-meth-oxy-1,2,3,4-tetra-hydro-isoquinolin-7-ol), C(12)H(17)NO(2), is a major alkaloid isolated from Hammada scoparia leaves. It belongs to the isoquinoline family and it was characterized by NMR spectroscopy and X-ray crystallographic techniques. The absolute configuration could not be reliably determined. An intermolecular O-H⋯N hydrogen bond is present in the crystal structure.

Related literature

For related literature on Hammada scoparia and isoquinoline alkaloids, see: Baker (1996 ▶); Benkrief et al. (1990 ▶); Carling & Sandberg (1970 ▶); El-Shazly & Wink (2003 ▶); El-Shazly et al. (2005 ▶); Iwasa et al. (2001 ▶); Jarraya & Damak (2001 ▶); Vetulani et al. (2001 ▶, 2003 ▶).

Experimental

Crystal data

C12H17NO2

M = 207.27

Orthorhombic,

a = 7.5942 (6) Å

b = 10.8082 (8) Å

c = 13.2716 (10) Å

V = 1089.33 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 (2) K

0.48 × 0.37 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (Becker & Coppens, 1974 ▶) T min = 0.961, T max = 0.988

23859 measured reflections

3132 independent reflections

2870 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.06

3132 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802477X/zl2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802477X/zl2131Isup2.hkl

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

C12H17NO2	Dx = 1.264 Mg m−3
Mr = 207.27	Melting point: 473 K
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2100 reflections
a = 7.5942 (6) Å	θ = 2.7–21.3º
b = 10.8082 (8) Å	µ = 0.09 mm−1
c = 13.2716 (10) Å	T = 200 (2) K
V = 1089.33 (14) Å3	Prism, colourless
Z = 4	0.48 × 0.37 × 0.22 mm
F000 = 448

Bruker SMART CCD area-detector diffractometer	3132 independent reflections
Radiation source: sealed tube	2870 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 200(2) K	θmax = 37.1º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(Becker & Coppens, 1974)	h = −12→10
Tmin = 0.961, Tmax = 0.988	k = −18→18
23859 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.028P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3132 reflections	Δρmax = 0.44 e Å−3
136 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.05540 (10)	0.85207 (7)	0.13064 (6)	0.01206 (13)
H1	0.0422	0.9013	0.0673	0.014*
C3	0.25806 (11)	0.83001 (8)	0.27194 (6)	0.01586 (14)
H3A	0.1557	0.8026	0.3124	0.019*
H3B	0.3386	0.8766	0.3167	0.019*
C4	0.35296 (11)	0.71807 (8)	0.22912 (6)	0.01475 (14)
H4A	0.4694	0.7437	0.2029	0.018*
H4B	0.3725	0.6567	0.2834	0.018*
C4A	0.24733 (10)	0.65931 (7)	0.14534 (6)	0.01156 (13)
C5	0.29165 (11)	0.54034 (7)	0.11057 (6)	0.01275 (13)
H5	0.3867	0.4973	0.1412	0.015*
C6	0.19977 (11)	0.48449 (7)	0.03258 (6)	0.01301 (13)
C7	0.05722 (11)	0.54781 (7)	−0.01256 (6)	0.01242 (13)
C8	0.01464 (10)	0.66497 (7)	0.02168 (6)	0.01194 (13)
H8	−0.0812	0.7078	−0.0084	0.014*
C8A	0.10928 (10)	0.72232 (7)	0.09969 (6)	0.01059 (12)
C10	0.14695 (12)	1.03330 (8)	0.22797 (7)	0.01802 (15)
H10A	0.1079	1.0854	0.1718	0.027*
H10B	0.2483	1.0720	0.2611	0.027*
H10C	0.0507	1.0242	0.2766	0.027*
C11	−0.12539 (11)	0.85179 (8)	0.18297 (7)	0.01757 (15)
H11A	−0.1569	0.9365	0.2022	0.026*
H11B	−0.1200	0.7998	0.2434	0.026*
H11C	−0.2144	0.8189	0.1367	0.026*
C12	0.37900 (13)	0.30406 (9)	0.03586 (8)	0.02182 (18)
H12A	0.3910	0.2239	0.0020	0.033*
H12B	0.3579	0.2908	0.1079	0.033*
H12C	0.4874	0.3520	0.0269	0.033*
N1	0.19793 (9)	0.91062 (6)	0.18960 (5)	0.01301 (12)
O1	0.23450 (9)	0.37016 (6)	−0.00665 (5)	0.01876 (13)
O2	−0.02759 (9)	0.49009 (5)	−0.08915 (5)	0.01773 (13)
H2	−0.1054	0.5372	−0.1126	0.027*

	U11	U22	U33	U12	U13	U23
C1	0.0121 (3)	0.0114 (3)	0.0127 (3)	0.0012 (2)	−0.0006 (2)	−0.0010 (2)
C3	0.0162 (3)	0.0185 (3)	0.0128 (3)	−0.0004 (3)	−0.0017 (3)	−0.0026 (3)
C4	0.0142 (3)	0.0154 (3)	0.0148 (3)	0.0000 (3)	−0.0041 (3)	−0.0009 (3)
C4A	0.0107 (3)	0.0121 (3)	0.0119 (3)	−0.0005 (2)	−0.0007 (2)	0.0007 (2)
C5	0.0119 (3)	0.0119 (3)	0.0144 (3)	0.0011 (2)	−0.0023 (2)	0.0009 (2)
C6	0.0132 (3)	0.0100 (3)	0.0159 (3)	0.0018 (2)	−0.0021 (3)	−0.0005 (2)
C7	0.0126 (3)	0.0102 (3)	0.0145 (3)	0.0007 (2)	−0.0027 (3)	−0.0004 (2)
C8	0.0116 (3)	0.0107 (3)	0.0135 (3)	0.0009 (2)	−0.0023 (2)	0.0000 (2)
C8A	0.0103 (3)	0.0100 (3)	0.0115 (3)	0.0001 (2)	−0.0002 (2)	0.0007 (2)
C10	0.0179 (4)	0.0149 (3)	0.0212 (3)	0.0006 (3)	0.0022 (3)	−0.0053 (3)
C11	0.0121 (3)	0.0191 (3)	0.0215 (3)	0.0012 (3)	0.0012 (3)	−0.0040 (3)
C12	0.0231 (4)	0.0173 (3)	0.0250 (4)	0.0099 (3)	−0.0070 (4)	−0.0022 (3)
N1	0.0132 (3)	0.0113 (3)	0.0145 (3)	−0.0006 (2)	0.0010 (2)	−0.0031 (2)
O1	0.0199 (3)	0.0113 (2)	0.0251 (3)	0.0056 (2)	−0.0085 (3)	−0.0043 (2)
O2	0.0189 (3)	0.0132 (2)	0.0211 (3)	0.0035 (2)	−0.0097 (2)	−0.0050 (2)

C1—N1	1.4780 (10)	C7—O2	1.3555 (10)
C1—C8A	1.5174 (10)	C7—C8	1.3837 (10)
C1—C11	1.5386 (12)	C8—C8A	1.4045 (10)
C1—H1	1.0000	C8—H8	0.9500
C3—N1	1.4703 (11)	C10—N1	1.4722 (10)
C3—C4	1.5185 (12)	C10—H10A	0.9800
C3—H3A	0.9900	C10—H10B	0.9800
C3—H3B	0.9900	C10—H10C	0.9800
C4—C4A	1.5110 (11)	C11—H11A	0.9800
C4—H4A	0.9900	C11—H11B	0.9800
C4—H4B	0.9900	C11—H11C	0.9800
C4A—C8A	1.3892 (10)	C12—O1	1.4257 (11)
C4A—C5	1.4070 (11)	C12—H12A	0.9800
C5—C6	1.3866 (11)	C12—H12B	0.9800
C5—H5	0.9500	C12—H12C	0.9800
C6—O1	1.3665 (10)	O2—H2	0.8400
C6—C7	1.4139 (11)
N1—C1—C8A	109.97 (6)	C7—C8—C8A	121.76 (7)
N1—C1—C11	114.55 (6)	C7—C8—H8	119.1
C8A—C1—C11	111.16 (7)	C8A—C8—H8	119.1
N1—C1—H1	106.9	C4A—C8A—C8	119.42 (7)
C8A—C1—H1	106.9	C4A—C8A—C1	122.58 (7)
C11—C1—H1	106.9	C8—C8A—C1	117.99 (7)
N1—C3—C4	109.96 (7)	N1—C10—H10A	109.5
N1—C3—H3A	109.7	N1—C10—H10B	109.5
C4—C3—H3A	109.7	H10A—C10—H10B	109.5
N1—C3—H3B	109.7	N1—C10—H10C	109.5
C4—C3—H3B	109.7	H10A—C10—H10C	109.5
H3A—C3—H3B	108.2	H10B—C10—H10C	109.5
C4A—C4—C3	110.99 (7)	C1—C11—H11A	109.5
C4A—C4—H4A	109.4	C1—C11—H11B	109.5
C3—C4—H4A	109.4	H11A—C11—H11B	109.5
C4A—C4—H4B	109.4	C1—C11—H11C	109.5
C3—C4—H4B	109.4	H11A—C11—H11C	109.5
H4A—C4—H4B	108.0	H11B—C11—H11C	109.5
C8A—C4A—C5	119.05 (7)	O1—C12—H12A	109.5
C8A—C4A—C4	121.03 (7)	O1—C12—H12B	109.5
C5—C4A—C4	119.90 (7)	H12A—C12—H12B	109.5
C6—C5—C4A	121.49 (7)	O1—C12—H12C	109.5
C6—C5—H5	119.3	H12A—C12—H12C	109.5
C4A—C5—H5	119.3	H12B—C12—H12C	109.5
O1—C6—C5	125.51 (7)	C3—N1—C10	111.00 (7)
O1—C6—C7	115.09 (7)	C3—N1—C1	111.54 (6)
C5—C6—C7	119.39 (7)	C10—N1—C1	112.10 (7)
O2—C7—C8	123.81 (7)	C6—O1—C12	116.80 (7)
O2—C7—C6	117.30 (7)	C7—O2—H2	109.5
C8—C7—C6	118.87 (7)
N1—C3—C4—C4A	−48.19 (9)	C4—C4A—C8A—C1	−0.30 (11)
C3—C4—C4A—C8A	15.68 (11)	C7—C8—C8A—C4A	−1.26 (12)
C3—C4—C4A—C5	−166.13 (7)	C7—C8—C8A—C1	178.70 (7)
C8A—C4A—C5—C6	−0.56 (12)	N1—C1—C8A—C4A	16.96 (10)
C4—C4A—C5—C6	−178.78 (7)	C11—C1—C8A—C4A	−110.97 (8)
C4A—C5—C6—O1	179.31 (8)	N1—C1—C8A—C8	−163.01 (7)
C4A—C5—C6—C7	−0.60 (12)	C11—C1—C8A—C8	69.06 (9)
O1—C6—C7—O2	−0.54 (11)	C4—C3—N1—C10	−165.48 (7)
C5—C6—C7—O2	179.38 (7)	C4—C3—N1—C1	68.74 (8)
O1—C6—C7—C8	−179.10 (7)	C8A—C1—N1—C3	−50.54 (8)
C5—C6—C7—C8	0.82 (12)	C11—C1—N1—C3	75.49 (8)
O2—C7—C8—C8A	−178.36 (8)	C8A—C1—N1—C10	−175.71 (6)
C6—C7—C8—C8A	0.10 (12)	C11—C1—N1—C10	−49.68 (9)
C5—C4A—C8A—C8	1.47 (11)	C5—C6—O1—C12	−0.82 (13)
C4—C4A—C8A—C8	179.67 (7)	C7—C6—O1—C12	179.10 (8)
C5—C4A—C8A—C1	−178.50 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.84	1.90	2.6970 (10)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.84	1.90	2.6970 (10)	159

Symmetry code: (i) .