6-Meth­oxy-1-(4-meth­oxy­phen­yl)-1,2,3,4-tetra­hydro-9H-β-carbolin-2-ium acetate

Goh, T.B.; Mordi, M.N.; Mansor, S.M.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536812016753

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1483

doi:10.1107/S1600536812016753

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6-Methoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydro-9H-β-carbolin-2-ium acetate

Teik Beng Goh,^a Mohd Nizam Mordi,^a Sharif Mahsufi Mansor,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*

^aCentre for Drug Research, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 3 April 2012; accepted 17 April 2012; online 21 April 2012)

In the title compound, C₁₉H₂₁N₂O₂⁺·C₂H₃O₂⁻, the 1H-indole ring system is essentially planar [maximum deviation = 0.0257 (14) Å] and forms a dihedral angle of 87.92 (7) Å with the benzene ring attached to the tetrahydropyridinium fragment. The tetrahydropyridinium ring adopts a half-chair conformation. In the crystal, cations and anions are linked by interionic N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds into chains along the a axis.

Related literature

For the biological activity of metal complexes with 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole, see: Al-Allaf et al. (1990 ); Herraiz et al. (2003 ). For a related tetrachloridozincate structure, see: Goh et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₂₁N₂O₂⁺·C₂H₃O₂⁻
M_r = 368.42
Monoclinic, P 2₁ /c
a = 9.1046 (4) Å
b = 19.8837 (8) Å
c = 12.0856 (5) Å
β = 123.281 (3)°
V = 1829.06 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.28 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.974, T_max = 0.985
21273 measured reflections
6211 independent reflections
4350 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.134
S = 1.03
6211 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O3ⁱ	0.93	1.86	2.7762 (15)	169
N1—H2⋯O3	0.90	1.93	2.7895 (19)	160
N2—H3⋯O4ⁱⁱ	0.97	1.72	2.6800 (18)	171
C9—H9A⋯O3ⁱⁱ	0.99	2.52	3.285 (2)	134
C10—H10A⋯N1ⁱ	1.00	2.55	3.4038 (19)	143
C15—H15A⋯O4ⁱⁱⁱ	0.95	2.60	3.5073 (19)	160
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016753/rz2738sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016753/rz2738Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016753/rz2738Isup3.cml

checkCIF report

Comment top

The metal complexes of 6-methoxy-1-methyl-4,9-dihydro-3H-β-carboline and other carboline alkaloids were previously reported to have biological activity (Al-Allaf et al. 1990). It is now well established that these class of beta carboline alkaloids may occur under mild conditions in foods from a Pictet-Spengler condensation of indoleamines such as L-tryptophan and short aliphatic aldehydes (Herraiz et al. 2003). Our present work intend to synthesize this compound and prepare it in salt form to investigate its safety and antiproliferative efficacy in cancer cell line.

All bond lengths and angles in the title compound (Fig. 1) are within normal ranges and comparable with those observed for a related compound recently reported (Goh et al., 2012). The 1H-indole ring (C1—C7/C11/N1) is planar with a maximum deviation of 0.0257 (14) Å for atom C11 and forms a dihedral angle of 87.92 (7)° with the C13—C18 benzene ring. The tetrahydropyridinium ring show a half-chair conformation with puckering parameters Q = 0.5216 (16) Å, θ = 52.70 (18)° and ϕ = 23.4 (2)°. In the crystal structure, cations and anions are linked by intermolecular N—H···O, C—H···O and C—H···N interactions (Table 1) into one-dimensional chains along the a axis (Fig. 2).

Related literature top

For the biological activity of metal complexes with 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole, see: Al-Allaf et al. (1990); Herraiz et al. (2003). For a related tetrachloridozincate structure, see: Goh et al. (2012). For the stability of the temperature controller use in the data collection, see: Cosier & Glazer (1986).

Experimental top

6-Methoxy-1-(4-methoxyphenyl)-4,9-dihydro-3H-β-carboline (2.50 mmol, 770 mg) was dissolved in analytical grade dichloromethane (0.60 ml). Vortex was performed to aid mixing. Glacial acetic acid (99.5%, 2.50 mmol, 145 µl) was transferred by a micropipette (50–200 µl) and was then added to the 6-methoxy-1-(4-methoxyphenyl)-4,9-dihydro-3H-β-carboline solution dropwise in a 20 ml glass bottle. The side of the glass bottle was scratched with a small spatula and the bottle was kept in fridge at 4° C for 60 days before yielding colourless crystals of 6-methoxy-1-(4-methoxyphenyl)-4,9-dihydro-3H-β-carbolinium acetate which were filtered off, washed twice with acetone and air-dried. Crystals of the title compound suitable for X-ray diffraction analysis were selected directly from the sample as prepared.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids. An interionic hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen interactions have been omitted for clarity.

6-Methoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydro-9H-β-carbolin-2-ium acetate top

Crystal data top

C₁₉H₂₁N₂O₂⁺·C₂H₃O₂⁻	F(000) = 784
M_r = 368.42	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5044 reflections
a = 9.1046 (4) Å	θ = 2.5–31.4°
b = 19.8837 (8) Å	µ = 0.09 mm⁻¹
c = 12.0856 (5) Å	T = 100 K
β = 123.281 (3)°	Block, colourless
V = 1829.06 (15) Å³	0.28 × 0.24 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6211 independent reflections
Radiation source: fine-focus sealed tube	4350 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 31.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→13
T_min = 0.974, T_max = 0.985	k = −25→29
21273 measured reflections	l = −17→17

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0554P)² + 0.5954P] where P = (F_o² + 2F_c²)/3
6211 reflections	(Δ/σ)_max = 0.001
247 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₂₁N₂O₂⁺·C₂H₃O₂⁻	V = 1829.06 (15) Å³
M_r = 368.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1046 (4) Å	µ = 0.09 mm⁻¹
b = 19.8837 (8) Å	T = 100 K
c = 12.0856 (5) Å	0.28 × 0.24 × 0.16 mm
β = 123.281 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4350 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.985	R_int = 0.045
21273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
6211 reflections	Δρ_min = −0.26 e Å⁻³
247 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.19801 (14)	0.80635 (6)	−0.51962 (10)	0.0206 (2)
O2	0.79721 (14)	0.79841 (5)	0.61132 (10)	0.0178 (2)
N1	0.53529 (15)	0.91336 (6)	−0.01734 (11)	0.0134 (2)
H2	0.6445	0.9291	0.0400	0.016*
N2	0.21849 (15)	0.94170 (6)	0.07834 (11)	0.0140 (2)
H1	0.1712	0.9749	0.0136	0.017*
H3	0.2114	0.9561	0.1518	0.017*
C1	0.47738 (18)	0.88736 (7)	−0.14119 (13)	0.0130 (3)
C2	0.56016 (19)	0.88480 (7)	−0.20957 (14)	0.0148 (3)
H2A	0.6767	0.9010	−0.1704	0.018*
C3	0.46785 (19)	0.85799 (7)	−0.33659 (14)	0.0153 (3)
H3A	0.5218	0.8559	−0.3851	0.018*
C4	0.29553 (19)	0.83388 (7)	−0.39423 (14)	0.0147 (3)
C5	0.21217 (19)	0.83642 (7)	−0.32661 (14)	0.0146 (3)
H5A	0.0956	0.8201	−0.3663	0.017*
C6	0.30332 (18)	0.86348 (7)	−0.19869 (13)	0.0121 (3)
C7	0.25808 (18)	0.87570 (7)	−0.10371 (13)	0.0134 (3)
C8	0.08984 (18)	0.86327 (8)	−0.11207 (14)	0.0151 (3)
H8A	0.0532	0.8159	−0.1371	0.018*
H8B	−0.0039	0.8926	−0.1808	0.018*
C9	0.11639 (19)	0.87798 (7)	0.02130 (14)	0.0151 (3)
H9A	0.0007	0.8823	0.0103	0.018*
H9B	0.1804	0.8402	0.0828	0.018*
C10	0.40804 (18)	0.93513 (7)	0.12006 (13)	0.0127 (3)
H10A	0.4582	0.9815	0.1352	0.015*
C11	0.40092 (18)	0.90627 (7)	0.00269 (13)	0.0126 (3)
C12	0.2764 (2)	0.80697 (9)	−0.59457 (15)	0.0215 (3)
H12A	0.1941	0.7879	−0.6825	0.032*
H12B	0.3843	0.7801	−0.5489	0.032*
H12C	0.3046	0.8534	−0.6038	0.032*
C13	0.51581 (18)	0.89668 (7)	0.24838 (13)	0.0129 (3)
C14	0.58947 (19)	0.93146 (8)	0.36854 (14)	0.0148 (3)
H14A	0.5734	0.9787	0.3680	0.018*
C15	0.68530 (19)	0.89756 (8)	0.48799 (14)	0.0153 (3)
H15A	0.7354	0.9215	0.5690	0.018*
C16	0.70801 (18)	0.82823 (7)	0.48899 (13)	0.0145 (3)
C17	0.63921 (19)	0.79301 (8)	0.37083 (14)	0.0157 (3)
H17A	0.6572	0.7459	0.3716	0.019*
C18	0.54363 (18)	0.82783 (7)	0.25149 (14)	0.0146 (3)
H18A	0.4965	0.8040	0.1707	0.018*
C19	0.8048 (2)	0.72675 (8)	0.61618 (16)	0.0229 (3)
H19A	0.8605	0.7118	0.7080	0.034*
H19B	0.8737	0.7108	0.5814	0.034*
H19C	0.6855	0.7084	0.5625	0.034*
O3	0.88167 (13)	0.95821 (5)	0.11028 (10)	0.0169 (2)
O4	1.16310 (14)	0.97876 (6)	0.26577 (10)	0.0201 (2)
C20	1.00753 (19)	0.96657 (7)	0.23013 (14)	0.0147 (3)
C21	0.9666 (2)	0.96257 (9)	0.33549 (16)	0.0247 (4)
H21A	1.0766	0.9612	0.4231	0.037*
H21B	0.8984	0.9218	0.3223	0.037*
H21C	0.8984	1.0022	0.3294	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0193 (5)	0.0309 (6)	0.0152 (5)	−0.0070 (5)	0.0118 (5)	−0.0087 (4)
O2	0.0180 (5)	0.0186 (6)	0.0123 (5)	0.0002 (4)	0.0055 (4)	0.0019 (4)
N1	0.0116 (5)	0.0171 (6)	0.0119 (5)	−0.0026 (5)	0.0068 (5)	−0.0014 (4)
N2	0.0131 (5)	0.0170 (6)	0.0120 (5)	0.0009 (5)	0.0071 (5)	−0.0009 (4)
C1	0.0138 (6)	0.0131 (7)	0.0121 (6)	0.0008 (5)	0.0072 (5)	−0.0006 (5)
C2	0.0129 (6)	0.0167 (7)	0.0166 (7)	−0.0008 (5)	0.0091 (6)	0.0000 (5)
C3	0.0168 (7)	0.0168 (7)	0.0172 (7)	−0.0009 (6)	0.0124 (6)	−0.0006 (5)
C4	0.0160 (6)	0.0158 (7)	0.0135 (6)	−0.0011 (6)	0.0090 (6)	−0.0017 (5)
C5	0.0135 (6)	0.0167 (7)	0.0148 (6)	−0.0014 (5)	0.0085 (6)	−0.0015 (5)
C6	0.0122 (6)	0.0129 (7)	0.0124 (6)	0.0008 (5)	0.0075 (5)	0.0010 (5)
C7	0.0134 (6)	0.0157 (7)	0.0134 (6)	0.0000 (5)	0.0088 (5)	−0.0002 (5)
C8	0.0132 (6)	0.0189 (7)	0.0149 (6)	−0.0029 (5)	0.0088 (5)	−0.0029 (5)
C9	0.0130 (6)	0.0186 (7)	0.0159 (6)	−0.0019 (5)	0.0092 (6)	−0.0020 (5)
C10	0.0118 (6)	0.0144 (7)	0.0128 (6)	−0.0005 (5)	0.0073 (5)	−0.0009 (5)
C11	0.0130 (6)	0.0137 (7)	0.0126 (6)	−0.0002 (5)	0.0081 (5)	0.0004 (5)
C12	0.0241 (8)	0.0294 (9)	0.0168 (7)	−0.0058 (7)	0.0149 (7)	−0.0066 (6)
C13	0.0112 (6)	0.0163 (7)	0.0127 (6)	−0.0008 (5)	0.0077 (5)	0.0005 (5)
C14	0.0151 (6)	0.0146 (7)	0.0159 (6)	−0.0012 (5)	0.0093 (6)	−0.0016 (5)
C15	0.0149 (6)	0.0185 (7)	0.0121 (6)	−0.0037 (5)	0.0072 (5)	−0.0042 (5)
C16	0.0107 (6)	0.0202 (7)	0.0125 (6)	−0.0007 (5)	0.0063 (5)	0.0009 (5)
C17	0.0173 (7)	0.0146 (7)	0.0154 (6)	0.0006 (5)	0.0091 (6)	−0.0004 (5)
C18	0.0160 (6)	0.0155 (7)	0.0124 (6)	−0.0019 (5)	0.0078 (6)	−0.0033 (5)
C19	0.0244 (8)	0.0191 (8)	0.0199 (7)	0.0013 (6)	0.0088 (7)	0.0042 (6)
O3	0.0134 (5)	0.0211 (6)	0.0150 (5)	−0.0002 (4)	0.0071 (4)	−0.0001 (4)
O4	0.0139 (5)	0.0313 (6)	0.0166 (5)	−0.0045 (4)	0.0092 (4)	−0.0069 (4)
C20	0.0152 (6)	0.0157 (7)	0.0152 (6)	0.0003 (5)	0.0097 (6)	−0.0008 (5)
C21	0.0240 (8)	0.0365 (10)	0.0200 (8)	−0.0023 (7)	0.0163 (7)	−0.0010 (7)

Geometric parameters (Å, º) top

O1—C4	1.3811 (17)	C9—H9B	0.9900
O1—C12	1.4283 (17)	C10—C11	1.4982 (18)
O2—C16	1.3708 (17)	C10—C13	1.5108 (19)
O2—C19	1.4263 (19)	C10—H10A	1.0000
N1—C11	1.3784 (17)	C12—H12A	0.9800
N1—C1	1.3855 (17)	C12—H12B	0.9800
N1—H2	0.9001	C12—H12C	0.9800
N2—C9	1.4972 (19)	C13—C18	1.389 (2)
N2—C10	1.5148 (17)	C13—C14	1.4028 (19)
N2—H1	0.9296	C14—C15	1.385 (2)
N2—H3	0.9674	C14—H14A	0.9500
C1—C2	1.3918 (18)	C15—C16	1.393 (2)
C1—C6	1.4182 (19)	C15—H15A	0.9500
C2—C3	1.390 (2)	C16—C17	1.3929 (19)
C2—H2A	0.9500	C17—C18	1.393 (2)
C3—C4	1.406 (2)	C17—H17A	0.9500
C3—H3A	0.9500	C18—H18A	0.9500
C4—C5	1.3882 (18)	C19—H19A	0.9800
C5—C6	1.4001 (19)	C19—H19B	0.9800
C5—H5A	0.9500	C19—H19C	0.9800
C6—C7	1.4371 (18)	O3—C20	1.2717 (17)
C7—C11	1.3707 (19)	O4—C20	1.2573 (17)
C7—C8	1.4993 (19)	C20—C21	1.512 (2)
C8—C9	1.5213 (19)	C21—H21A	0.9800
C8—H8A	0.9900	C21—H21B	0.9800
C8—H8B	0.9900	C21—H21C	0.9800
C9—H9A	0.9900

C4—O1—C12	116.63 (11)	C13—C10—N2	111.40 (11)
C16—O2—C19	117.59 (11)	C11—C10—H10A	107.7
C11—N1—C1	107.65 (11)	C13—C10—H10A	107.7
C11—N1—H2	127.8	N2—C10—H10A	107.7
C1—N1—H2	124.4	C7—C11—N1	110.93 (12)
C9—N2—C10	112.73 (11)	C7—C11—C10	125.72 (12)
C9—N2—H1	109.2	N1—C11—C10	123.06 (12)
C10—N2—H1	105.0	O1—C12—H12A	109.5
C9—N2—H3	109.6	O1—C12—H12B	109.5
C10—N2—H3	110.9	H12A—C12—H12B	109.5
H1—N2—H3	109.2	O1—C12—H12C	109.5
N1—C1—C2	130.25 (13)	H12A—C12—H12C	109.5
N1—C1—C6	108.34 (11)	H12B—C12—H12C	109.5
C2—C1—C6	121.36 (12)	C18—C13—C14	118.77 (13)
C3—C2—C1	118.27 (13)	C18—C13—C10	122.18 (12)
C3—C2—H2A	120.9	C14—C13—C10	119.04 (13)
C1—C2—H2A	120.9	C15—C14—C13	120.61 (14)
C2—C3—C4	120.81 (12)	C15—C14—H14A	119.7
C2—C3—H3A	119.6	C13—C14—H14A	119.7
C4—C3—H3A	119.6	C14—C15—C16	119.76 (13)
O1—C4—C5	115.49 (12)	C14—C15—H15A	120.1
O1—C4—C3	123.33 (12)	C16—C15—H15A	120.1
C5—C4—C3	121.18 (13)	O2—C16—C17	123.73 (13)
C4—C5—C6	118.67 (13)	O2—C16—C15	115.76 (12)
C4—C5—H5A	120.7	C17—C16—C15	120.50 (13)
C6—C5—H5A	120.7	C18—C17—C16	119.06 (14)
C5—C6—C1	119.71 (12)	C18—C17—H17A	120.5
C5—C6—C7	133.71 (13)	C16—C17—H17A	120.5
C1—C6—C7	106.56 (12)	C13—C18—C17	121.27 (13)
C11—C7—C6	106.50 (12)	C13—C18—H18A	119.4
C11—C7—C8	123.00 (12)	C17—C18—H18A	119.4
C6—C7—C8	130.41 (13)	O2—C19—H19A	109.5
C7—C8—C9	109.54 (11)	O2—C19—H19B	109.5
C7—C8—H8A	109.8	H19A—C19—H19B	109.5
C9—C8—H8A	109.8	O2—C19—H19C	109.5
C7—C8—H8B	109.8	H19A—C19—H19C	109.5
C9—C8—H8B	109.8	H19B—C19—H19C	109.5
H8A—C8—H8B	108.2	O4—C20—O3	123.85 (13)
N2—C9—C8	110.37 (11)	O4—C20—C21	118.25 (13)
N2—C9—H9A	109.6	O3—C20—C21	117.90 (13)
C8—C9—H9A	109.6	C20—C21—H21A	109.5
N2—C9—H9B	109.6	C20—C21—H21B	109.5
C8—C9—H9B	109.6	H21A—C21—H21B	109.5
H9A—C9—H9B	108.1	C20—C21—H21C	109.5
C11—C10—C13	116.38 (12)	H21A—C21—H21C	109.5
C11—C10—N2	105.57 (11)	H21B—C21—H21C	109.5

C11—N1—C1—C2	177.32 (15)	C6—C7—C11—N1	−0.96 (16)
C11—N1—C1—C6	−0.18 (15)	C8—C7—C11—N1	−177.99 (13)
N1—C1—C2—C3	−177.32 (14)	C6—C7—C11—C10	173.05 (13)
C6—C1—C2—C3	−0.1 (2)	C8—C7—C11—C10	−4.0 (2)
C1—C2—C3—C4	−0.2 (2)	C1—N1—C11—C7	0.73 (16)
C12—O1—C4—C5	176.19 (13)	C1—N1—C11—C10	−173.47 (13)
C12—O1—C4—C3	−3.9 (2)	C13—C10—C11—C7	108.15 (16)
C2—C3—C4—O1	−179.57 (14)	N2—C10—C11—C7	−15.97 (19)
C2—C3—C4—C5	0.4 (2)	C13—C10—C11—N1	−78.52 (17)
O1—C4—C5—C6	179.77 (13)	N2—C10—C11—N1	157.36 (13)
C3—C4—C5—C6	−0.2 (2)	C11—C10—C13—C18	−26.91 (19)
C4—C5—C6—C1	−0.1 (2)	N2—C10—C13—C18	94.16 (15)
C4—C5—C6—C7	177.79 (15)	C11—C10—C13—C14	153.50 (12)
N1—C1—C6—C5	178.05 (13)	N2—C10—C13—C14	−85.42 (15)
C2—C1—C6—C5	0.3 (2)	C18—C13—C14—C15	−1.2 (2)
N1—C1—C6—C7	−0.39 (15)	C10—C13—C14—C15	178.38 (12)
C2—C1—C6—C7	−178.16 (13)	C13—C14—C15—C16	−0.4 (2)
C5—C6—C7—C11	−177.31 (16)	C19—O2—C16—C17	−6.2 (2)
C1—C6—C7—C11	0.82 (16)	C19—O2—C16—C15	172.50 (13)
C5—C6—C7—C8	−0.6 (3)	C14—C15—C16—O2	−176.91 (12)
C1—C6—C7—C8	177.54 (14)	C14—C15—C16—C17	1.8 (2)
C11—C7—C8—C9	−9.9 (2)	O2—C16—C17—C18	177.02 (13)
C6—C7—C8—C9	173.87 (14)	C15—C16—C17—C18	−1.6 (2)
C10—N2—C9—C8	−69.07 (14)	C14—C13—C18—C17	1.4 (2)
C7—C8—C9—N2	43.56 (16)	C10—C13—C18—C17	−178.14 (13)
C9—N2—C10—C11	51.16 (14)	C16—C17—C18—C13	−0.1 (2)
C9—N2—C10—C13	−76.04 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O3ⁱ	0.93	1.86	2.7762 (15)	169
N1—H2···O3	0.90	1.93	2.7895 (19)	160
N2—H3···O4ⁱⁱ	0.97	1.72	2.6800 (18)	171
C9—H9A···O3ⁱⁱ	0.99	2.52	3.285 (2)	134
C10—H10A···N1ⁱ	1.00	2.55	3.4038 (19)	143
C15—H15A···O4ⁱⁱⁱ	0.95	2.60	3.5073 (19)	160

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁N₂O₂⁺·C₂H₃O₂⁻
M_r	368.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.1046 (4), 19.8837 (8), 12.0856 (5)
β (°)	123.281 (3)
V (Å³)	1829.06 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.974, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	21273, 6211, 4350
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.740

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.134, 1.03
No. of reflections	6211
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O3ⁱ	0.9300	1.8600	2.7762 (15)	169.00
N1—H2···O3	0.9000	1.9300	2.7895 (19)	160.00
N2—H3···O4ⁱⁱ	0.9700	1.7200	2.6800 (18)	171.00
C9—H9A···O3ⁱⁱ	0.9900	2.5200	3.285 (2)	134.00
C10—H10A···N1ⁱ	1.0000	2.5500	3.4038 (19)	143.00
C15—H15A···O4ⁱⁱⁱ	0.9500	2.6000	3.5073 (19)	160.00

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

Acknowledgements

This work was supported by USM Research University Grant No. 1001/CDADAH/815020 and the R&D Initiative Fund, Ministry of Science, Technology and Innovation, Malaysia (MOSTI). HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160.

References

Al-Allaf, T. A. K., Ayoub, M. T. & Rashan, L. J. (1990). J. Inorg. Biochem. 38, 47–56. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goh, T. B., Mordi, M. N., Mansor, S. M., Rosli, M. M. & Fun, H.-K. (2012). Acta Cryst. E68, m464–m465. CSD CrossRef IUCr Journals Google Scholar
Herraiz, T., Galisteo, J. & Chamorro, C. (2003). J. Agric. Food Chem. 51, 2168–2173. Web of Science CrossRef PubMed CAS Google Scholar
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

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Volume 68| Part 5| May 2012| Page o1483

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-Meth­­oxy-1-(4-meth­­oxy­phen­yl)-1,2,3,4-tetra­hydro-9H-β-carbolin-2-ium acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Methoxy-1-(4-methoxyphenyl)-1,2,3,4-tetrahydro-9H-β-carbolin-2-ium acetate