(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-meth­oxy-1,2,3,4,6,7,12,12b-octa­hydro­indolo[2,3-a]quinolizin-2-yl]-3-methoxy­acrylate ethanol solvate

Carvalho, P.; Furr III, E.B.; McCurdy, C.

doi:10.1107/S1600536809017309

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1441-o1442

doi:10.1107/S1600536809017309

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(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate

Paulo Carvalho,^a Edward B. Furr III ^a and Christopher McCurdy ^b ^*

^aDepartment of Medicinal Chemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA, and ^bDepartment of Medicinal Chemistry and Department of Pharmacology, University of Mississippi, 417 Faser Hall, University, MS 38677, USA
^*Correspondence e-mail: cmccurdy@olemiss.edu

(Received 24 April 2009; accepted 8 May 2009; online 29 May 2009)

In the title compound, C₂₃H₃₀N₂O₄·C₂H₆O, the indole derivative has four fused rings, forming an indolo[2-3a]quinolizine system, in which one six-membered ring is directly connected to the indole unit and has a distorted chair conformation. The fourth ring is also a six-membered ring, depicting a regular chair conformation. In the crystal, the molecules are linked by N—H⋯O and O—H⋯N interactions, forming a C(7) chain.

Related literature

For previous crystallographic analysis of mitragynine salts (hydrobromide and hydroiodide), see: Zacharias et al. (1965 ). For the method of extraction, see: Ponglux et al. (1994 ). For synthetic studies, see: Ma et al. (2009 ). For medicinal properties, see: Boyer et al. (2008 ); Weibrecht et al. (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₃H₃₀N₂O₄·C₂H₆O
M_r = 444.56
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.60450 (10) Å
b = 11.7534 (2) Å
c = 26.5735 (4) Å
V = 2375.11 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.12 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: none
34365 measured reflections
4158 independent reflections
3649 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.089
S = 1.05
4158 reflections
295 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1758 Friedel pairs
Flack parameter: 0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	2.07	2.876 (2)	169
N1—H1⋯O5ⁱ	0.86	2.01	2.866 (2)	170
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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); software used to prepare material for publication: SHELXTL and ORTEP-3 (Farrugia, 1997 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017309/bx2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017309/bx2206Isup2.hkl

checkCIF report

Comment top

Kratom (Mitragynia speciosa korth) is a medicinal herb endogenous to southeast Asia traditionally used as a treatment for opium withdrawal. Patients with chronic pain are increasingly aware of kratom as opioid replacement therapy. Mitragynine, the predominant alkaloid of kratom, binds with high affinity at human adrenergic, serotinergic, and adenosine CNS receptors. The binding affinity of mitragynine at mu (KD = 204 plus or minus 26 nM), delta (KD = 2250 plus or minus 47nM) and kappa (KD = 455 plus or minus 47 nM) receptors suggest that the mu-opioid agonism of mitragynine may minimize opioid withdrawal symptoms; as a kappa agonist, the molecule may oppose mu-opioid effects to modulatere inforcement and produce aversion. Furthermore, adrenergic agonist activity at alpha-2 receptors may permit kratom to mimic adjunctive therapies for opioid withdrawal such as clonidine (Weibrecht et al., 2008). The title compound has four fused rings, forming an indolo[2-3a]quinolizine system, in which one six-membered ring is directly connected to the indol moiety and has a distorted chair conformation. The fourth ring is also a six-membered ring, depicting a regular chair conformation. The molecules are linked by N—H···O and O—H···N interactions, forming a chain C(7) (Bernstein et al., 1995) along [100] directions (Fig. 2).

Related literature top

For previous crystallographic analysis of mitragynine salts (hydrobromide and hydroiodide), see: Zacharias et al. (1965). For the method of extraction, see: Ponglux et al. (1994). For synthetic studies, see: Ma et al. (2009). For medicinal properties, see: Boyer et al. (2008); Weibrecht et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Mitragynine was extracted from dried M. speciosa leaves according to the procedure published by Ponglux et al., (1994), and crystallized from a solution in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound, showing the formation of a C(7) chain, along [100]. H atoms not involved in this motiv were omitted for the sake of clarity.

(E)-methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate top

Crystal data top

C₂₃H₃₀N₂O₄·C₂H₆O	F(000) = 960
M_r = 444.56	D_x = 1.243 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3152 reflections
a = 7.6045 (1) Å	θ = 3.3–64.6°
b = 11.7534 (2) Å	µ = 0.70 mm⁻¹
c = 26.5735 (4) Å	T = 100 K
V = 2375.11 (6) Å³	Needle, colourless
Z = 4	0.12 × 0.09 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	3649 reflections with I > 2σ(I)
Radiation source: Sealed Tube	R_int = 0.083
Graphite monochromator	θ_max = 66.4°, θ_min = 3.3°
ϕ and ω scans	h = −9→9
34365 measured reflections	k = −13→13
4158 independent reflections	l = −31→31

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0469P)² + 0.2771P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4158 reflections	Δρ_max = 0.19 e Å⁻³
295 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1758 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (2)

Crystal data top

C₂₃H₃₀N₂O₄·C₂H₆O	V = 2375.11 (6) Å³
M_r = 444.56	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 7.6045 (1) Å	µ = 0.70 mm⁻¹
b = 11.7534 (2) Å	T = 100 K
c = 26.5735 (4) Å	0.12 × 0.09 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	3649 reflections with I > 2σ(I)
34365 measured reflections	R_int = 0.083
4158 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.089	Δρ_max = 0.19 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
4158 reflections	Absolute structure: Flack (1983), 1758 Friedel pairs
295 parameters	Absolute structure parameter: 0.2 (2)
0 restraints

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
C3	0.3530 (3)	0.08591 (16)	0.79611 (7)	0.0226 (4)
H3	0.2920	0.0127	0.7987	0.027*
C2	0.3100 (3)	0.13687 (16)	0.74583 (7)	0.0224 (4)
C14	0.2990 (3)	0.15900 (16)	0.84110 (7)	0.0224 (4)
H14A	0.1750	0.1778	0.8388	0.027*
H14B	0.3657	0.2293	0.8412	0.027*
C5	0.6061 (3)	0.00338 (18)	0.75273 (7)	0.0269 (5)
H5A	0.5360	−0.0647	0.7479	0.032*
H5B	0.7275	−0.0197	0.7574	0.032*
C16	0.2800 (3)	0.14709 (17)	0.93877 (7)	0.0237 (4)
C21	0.5794 (3)	−0.00691 (16)	0.84300 (7)	0.0245 (4)
H21A	0.7032	−0.0267	0.8439	0.029*
H21B	0.5124	−0.0769	0.8405	0.029*
C20	0.5303 (3)	0.05433 (16)	0.89183 (7)	0.0228 (4)
H20	0.5406	−0.0014	0.9191	0.027*
C7	0.4161 (3)	0.13592 (16)	0.70469 (7)	0.0234 (4)
C11	0.0631 (3)	0.29780 (17)	0.60685 (8)	0.0301 (5)
H11	−0.0215	0.3322	0.5867	0.036*
C17	0.2551 (3)	0.25695 (16)	0.94916 (7)	0.0257 (4)
H17	0.2198	0.2764	0.9815	0.031*
C8	0.3190 (3)	0.19029 (16)	0.66512 (7)	0.0231 (4)
C10	0.2287 (3)	0.27195 (17)	0.58613 (7)	0.0281 (5)
H10	0.2523	0.2904	0.5528	0.034*
C6	0.5923 (3)	0.07864 (19)	0.70579 (8)	0.0286 (5)
H6A	0.6847	0.1355	0.7063	0.034*
H6B	0.6070	0.0325	0.6758	0.034*
C15	0.3348 (3)	0.09212 (16)	0.88976 (7)	0.0226 (4)
H15	0.2658	0.0220	0.8871	0.027*
C9	0.3566 (3)	0.21944 (17)	0.61479 (7)	0.0246 (4)
C13	0.1537 (3)	0.21960 (17)	0.68469 (7)	0.0241 (4)
C12	0.0231 (3)	0.27357 (17)	0.65616 (7)	0.0281 (4)
H12	−0.0856	0.2921	0.6699	0.034*
C19	0.6535 (3)	0.15316 (18)	0.90462 (8)	0.0268 (4)
H19A	0.6527	0.2068	0.8769	0.032*
H19B	0.6081	0.1923	0.9340	0.032*
C18	0.8419 (3)	0.1177 (2)	0.91491 (9)	0.0359 (5)
H18A	0.8946	0.0905	0.8844	0.054*
H18B	0.8432	0.0583	0.9397	0.054*
H18C	0.9071	0.1819	0.9272	0.054*
C24	0.2472 (3)	0.06448 (17)	0.98062 (7)	0.0245 (4)
C22	0.5687 (3)	0.2261 (2)	0.54835 (8)	0.0362 (5)
H22A	0.5535	0.3068	0.5450	0.054*
H22B	0.4941	0.1875	0.5247	0.054*
H22C	0.6892	0.2066	0.5418	0.054*
C25	0.2001 (4)	0.0389 (2)	1.06740 (8)	0.0398 (6)
H25A	0.2861	−0.0208	1.0688	0.060*
H25B	0.0856	0.0065	1.0623	0.060*
H25C	0.2013	0.0808	1.0984	0.060*
C23	0.2173 (4)	0.45082 (18)	0.93323 (9)	0.0393 (6)
H23A	0.2795	0.4710	0.9634	0.059*
H23B	0.0936	0.4468	0.9402	0.059*
H23C	0.2384	0.5073	0.9079	0.059*
C27	0.7975 (3)	0.33626 (19)	0.79406 (9)	0.0404 (6)
H27A	0.6948	0.3492	0.8149	0.048*
H27B	0.7713	0.3627	0.7603	0.048*
C26	0.9507 (4)	0.4008 (2)	0.81476 (12)	0.0505 (7)
H26A	1.0519	0.3881	0.7939	0.076*
H26B	0.9750	0.3752	0.8484	0.076*
H26C	0.9235	0.4806	0.8153	0.076*
N2	0.5446 (2)	0.06406 (13)	0.79818 (6)	0.0223 (4)
N1	0.1505 (2)	0.18655 (14)	0.73471 (6)	0.0237 (4)
H1	0.0642	0.1955	0.7552	0.028*
O5	0.83716 (18)	0.21863 (12)	0.79292 (5)	0.0297 (3)
H5	0.7462	0.1818	0.7960	0.045*
O3	0.2266 (2)	−0.03588 (11)	0.97486 (5)	0.0323 (3)
O2	0.2782 (2)	0.34155 (11)	0.91554 (5)	0.0303 (3)
O1	0.52291 (19)	0.19211 (12)	0.59849 (5)	0.0310 (3)
O4	0.2410 (2)	0.11472 (11)	1.02612 (5)	0.0343 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.0226 (10)	0.0251 (10)	0.0201 (9)	0.0001 (8)	0.0008 (9)	0.0000 (8)
C2	0.0197 (10)	0.0247 (10)	0.0226 (9)	−0.0004 (8)	−0.0025 (8)	−0.0016 (8)
C14	0.0200 (10)	0.0273 (10)	0.0200 (9)	0.0005 (8)	−0.0001 (8)	−0.0007 (8)
C5	0.0234 (11)	0.0319 (11)	0.0253 (10)	0.0065 (9)	−0.0002 (8)	−0.0038 (8)
C16	0.0182 (10)	0.0317 (10)	0.0213 (9)	−0.0008 (8)	0.0002 (8)	−0.0010 (8)
C21	0.0229 (10)	0.0281 (10)	0.0226 (10)	0.0029 (8)	−0.0003 (8)	0.0007 (8)
C20	0.0224 (11)	0.0282 (10)	0.0177 (9)	0.0038 (8)	−0.0005 (8)	0.0026 (8)
C7	0.0236 (10)	0.0263 (10)	0.0204 (9)	−0.0017 (8)	−0.0004 (8)	−0.0023 (8)
C11	0.0329 (12)	0.0302 (11)	0.0273 (10)	−0.0005 (9)	−0.0086 (9)	0.0016 (9)
C17	0.0236 (11)	0.0309 (11)	0.0227 (10)	−0.0034 (9)	0.0005 (9)	0.0013 (8)
C8	0.0258 (11)	0.0237 (9)	0.0197 (9)	−0.0041 (8)	−0.0009 (8)	−0.0026 (7)
C10	0.0363 (12)	0.0287 (10)	0.0193 (9)	−0.0048 (10)	−0.0024 (9)	0.0007 (8)
C6	0.0255 (11)	0.0397 (12)	0.0207 (10)	0.0034 (9)	0.0019 (9)	−0.0028 (9)
C15	0.0209 (10)	0.0257 (10)	0.0213 (10)	−0.0012 (8)	0.0009 (8)	−0.0010 (8)
C9	0.0272 (11)	0.0255 (10)	0.0212 (9)	−0.0043 (8)	0.0018 (9)	−0.0041 (8)
C13	0.0262 (11)	0.0243 (9)	0.0218 (9)	−0.0031 (8)	−0.0015 (8)	−0.0015 (8)
C12	0.0260 (11)	0.0293 (11)	0.0291 (10)	−0.0008 (9)	−0.0026 (9)	0.0009 (9)
C19	0.0235 (11)	0.0340 (11)	0.0229 (10)	0.0016 (9)	−0.0020 (9)	−0.0024 (8)
C18	0.0241 (12)	0.0469 (14)	0.0366 (12)	0.0017 (10)	−0.0020 (10)	−0.0038 (10)
C24	0.0181 (10)	0.0314 (11)	0.0240 (10)	0.0005 (9)	0.0029 (9)	−0.0051 (8)
C22	0.0450 (14)	0.0369 (12)	0.0265 (11)	−0.0045 (11)	0.0109 (10)	0.0016 (9)
C25	0.0561 (17)	0.0359 (12)	0.0275 (11)	−0.0033 (11)	0.0084 (11)	0.0037 (9)
C23	0.0493 (15)	0.0280 (11)	0.0406 (13)	0.0020 (11)	0.0050 (11)	0.0023 (9)
C27	0.0389 (14)	0.0370 (12)	0.0452 (13)	0.0090 (10)	0.0105 (12)	0.0091 (10)
C26	0.0404 (15)	0.0308 (13)	0.0804 (19)	0.0015 (11)	0.0045 (14)	−0.0067 (13)
N2	0.0185 (8)	0.0288 (9)	0.0196 (8)	0.0024 (7)	−0.0006 (7)	−0.0012 (7)
N1	0.0217 (9)	0.0294 (8)	0.0201 (8)	0.0026 (7)	0.0026 (7)	0.0002 (7)
O5	0.0237 (7)	0.0330 (7)	0.0326 (8)	0.0005 (6)	0.0038 (7)	0.0013 (6)
O3	0.0413 (9)	0.0279 (8)	0.0276 (7)	−0.0012 (7)	0.0041 (7)	0.0005 (6)
O2	0.0394 (9)	0.0246 (7)	0.0269 (7)	0.0017 (7)	0.0045 (6)	−0.0020 (5)
O1	0.0348 (9)	0.0368 (8)	0.0215 (7)	−0.0023 (7)	0.0047 (6)	0.0005 (6)
O4	0.0527 (10)	0.0285 (7)	0.0216 (7)	−0.0041 (7)	0.0050 (7)	0.0012 (6)

Geometric parameters (Å, º) top

C3—N2	1.481 (3)	C6—H6B	0.9700
C3—C2	1.500 (3)	C15—H15	0.9800
C3—C14	1.528 (2)	C9—O1	1.375 (2)
C3—H3	0.9800	C13—N1	1.385 (2)
C2—C7	1.359 (3)	C13—C12	1.401 (3)
C2—N1	1.378 (3)	C12—H12	0.9300
C14—C15	1.538 (2)	C19—C18	1.517 (3)
C14—H14A	0.9700	C19—H19A	0.9700
C14—H14B	0.9700	C19—H19B	0.9700
C5—N2	1.479 (2)	C18—H18A	0.9600
C5—C6	1.533 (3)	C18—H18B	0.9600
C5—H5A	0.9700	C18—H18C	0.9600
C5—H5B	0.9700	C24—O3	1.200 (2)
C16—C17	1.334 (3)	C24—O4	1.346 (2)
C16—C24	1.497 (3)	C22—O1	1.434 (2)
C16—C15	1.512 (3)	C22—H22A	0.9600
C21—N2	1.478 (2)	C22—H22B	0.9600
C21—C20	1.530 (3)	C22—H22C	0.9600
C21—H21A	0.9700	C25—O4	1.447 (2)
C21—H21B	0.9700	C25—H25A	0.9600
C20—C19	1.530 (3)	C25—H25B	0.9600
C20—C15	1.553 (3)	C25—H25C	0.9600
C20—H20	0.9800	C23—O2	1.444 (3)
C7—C8	1.435 (3)	C23—H23A	0.9600
C7—C6	1.500 (3)	C23—H23B	0.9600
C11—C12	1.375 (3)	C23—H23C	0.9600
C11—C10	1.408 (3)	C27—O5	1.415 (3)
C11—H11	0.9300	C27—C26	1.495 (4)
C17—O2	1.348 (2)	C27—H27A	0.9700
C17—H17	0.9300	C27—H27B	0.9700
C8—C13	1.403 (3)	C26—H26A	0.9600
C8—C9	1.410 (3)	C26—H26B	0.9600
C10—C9	1.381 (3)	C26—H26C	0.9600
C10—H10	0.9300	N1—H1	0.8600
C6—H6A	0.9700	O5—H5	0.8200

N2—C3—C2	108.46 (15)	O1—C9—C8	115.38 (17)
N2—C3—C14	109.44 (16)	C10—C9—C8	119.27 (18)
C2—C3—C14	114.45 (16)	N1—C13—C12	129.34 (18)
N2—C3—H3	108.1	N1—C13—C8	107.59 (17)
C2—C3—H3	108.1	C12—C13—C8	123.07 (18)
C14—C3—H3	108.1	C11—C12—C13	116.90 (19)
C7—C2—N1	110.71 (16)	C11—C12—H12	121.5
C7—C2—C3	125.74 (18)	C13—C12—H12	121.5
N1—C2—C3	123.47 (17)	C18—C19—C20	114.17 (18)
C3—C14—C15	108.83 (15)	C18—C19—H19A	108.7
C3—C14—H14A	109.9	C20—C19—H19A	108.7
C15—C14—H14A	109.9	C18—C19—H19B	108.7
C3—C14—H14B	109.9	C20—C19—H19B	108.7
C15—C14—H14B	109.9	H19A—C19—H19B	107.6
H14A—C14—H14B	108.3	C19—C18—H18A	109.5
N2—C5—C6	111.38 (16)	C19—C18—H18B	109.5
N2—C5—H5A	109.4	H18A—C18—H18B	109.5
C6—C5—H5A	109.4	C19—C18—H18C	109.5
N2—C5—H5B	109.4	H18A—C18—H18C	109.5
C6—C5—H5B	109.4	H18B—C18—H18C	109.5
H5A—C5—H5B	108.0	O3—C24—O4	122.76 (18)
C17—C16—C24	116.77 (17)	O3—C24—C16	124.37 (17)
C17—C16—C15	129.11 (18)	O4—C24—C16	112.86 (16)
C24—C16—C15	114.11 (16)	O1—C22—H22A	109.5
N2—C21—C20	111.97 (15)	O1—C22—H22B	109.5
N2—C21—H21A	109.2	H22A—C22—H22B	109.5
C20—C21—H21A	109.2	O1—C22—H22C	109.5
N2—C21—H21B	109.2	H22A—C22—H22C	109.5
C20—C21—H21B	109.2	H22B—C22—H22C	109.5
H21A—C21—H21B	107.9	O4—C25—H25A	109.5
C21—C20—C19	113.32 (17)	O4—C25—H25B	109.5
C21—C20—C15	109.77 (16)	H25A—C25—H25B	109.5
C19—C20—C15	112.13 (16)	O4—C25—H25C	109.5
C21—C20—H20	107.1	H25A—C25—H25C	109.5
C19—C20—H20	107.1	H25B—C25—H25C	109.5
C15—C20—H20	107.1	O2—C23—H23A	109.5
C2—C7—C8	106.27 (17)	O2—C23—H23B	109.5
C2—C7—C6	121.23 (18)	H23A—C23—H23B	109.5
C8—C7—C6	132.39 (18)	O2—C23—H23C	109.5
C12—C11—C10	121.73 (19)	H23A—C23—H23C	109.5
C12—C11—H11	119.1	H23B—C23—H23C	109.5
C10—C11—H11	119.1	O5—C27—C26	109.7 (2)
C16—C17—O2	123.94 (18)	O5—C27—H27A	109.7
C16—C17—H17	118.0	C26—C27—H27A	109.7
O2—C17—H17	118.0	O5—C27—H27B	109.7
C13—C8—C9	118.26 (18)	C26—C27—H27B	109.7
C13—C8—C7	107.40 (16)	H27A—C27—H27B	108.2
C9—C8—C7	134.32 (19)	C27—C26—H26A	109.5
C9—C10—C11	120.73 (18)	C27—C26—H26B	109.5
C9—C10—H10	119.6	H26A—C26—H26B	109.5
C11—C10—H10	119.6	C27—C26—H26C	109.5
C7—C6—C5	109.66 (16)	H26A—C26—H26C	109.5
C7—C6—H6A	109.7	H26B—C26—H26C	109.5
C5—C6—H6A	109.7	C21—N2—C5	109.23 (14)
C7—C6—H6B	109.7	C21—N2—C3	107.72 (15)
C5—C6—H6B	109.7	C5—N2—C3	111.39 (15)
H6A—C6—H6B	108.2	C2—N1—C13	108.02 (16)
C16—C15—C14	117.18 (16)	C2—N1—H1	126.0
C16—C15—C20	110.83 (16)	C13—N1—H1	126.0
C14—C15—C20	110.24 (15)	C27—O5—H5	109.5
C16—C15—H15	105.9	C17—O2—C23	113.49 (15)
C14—C15—H15	105.9	C9—O1—C22	116.81 (16)
C20—C15—H15	105.9	C24—O4—C25	114.73 (16)
O1—C9—C10	125.35 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	2.07	2.876 (2)	169
N1—H1···O5ⁱ	0.86	2.01	2.866 (2)	170

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀N₂O₄·C₂H₆O
M_r	444.56
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.6045 (1), 11.7534 (2), 26.5735 (4)
V (Å³)	2375.11 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.12 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	34365, 4158, 3649
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.089, 1.05
No. of reflections	4158
No. of parameters	295
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18
Absolute structure	Flack (1983), 1758 Friedel pairs
Absolute structure parameter	0.2 (2)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	2.07	2.876 (2)	169.1
N1—H1···O5ⁱ	0.86	2.01	2.866 (2)	170.4

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by the NIH–NCRR (grant No. 5P20RR021919). The authors also thank the Center for Disease Control and Prevention, USA, for providing financial assistance (CDC cooperative agreements 1UO1 CI000211-03 and 1UO1 CI000362-01). This investigation was conducted in a facility constructed with support from Research Facilities Improvement Program grant No. C06Rr-14503-01 from the National Center for Research Resources, National Institutes of Health.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 65| Part 6| June 2009| Pages o1441-o1442

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

(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-meth­­oxy-1,2,3,4,6,7,12,12b-octa­hydro­indolo[2,3-a]quinolizin-2-yl]-3-meth­oxy­acrylate ethanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate