(1S,3S)-Methyl 6,7-dimeth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinoline-3-carboxyl­ate

Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811018782

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1501

doi:10.1107/S1600536811018782

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(1S,3S)-Methyl 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Tricia Naicker,^a Thavendran Govender,^a Hendrik G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^aSchool of Pharmacy and Pharmacology, University of KwaZulu Natal, Durban 4000, South Africa, and ^bSchool of Chemistry, University of KwaZulu Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 15 May 2011; accepted 17 May 2011; online 25 May 2011)

In the title compound, C₁₉H₂₁NO₄, an organocatalyst with a tetrahydroisoquinoline backbone, the heterocyclic ring assumes a half-boat conformation. The dihedral angle between the aromatic rings is 82.93 (8)°. In the crystal, molecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming a layer parallel to (10 $[\overline{1}]$ ).

Related literature

For related structures, see: Naicker et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₉H₂₁NO₄
M_r = 327.37
Monoclinic, P 2₁
a = 9.3841 (3) Å
b = 6.3453 (2) Å
c = 14.2048 (4) Å
β = 94.475 (2)°
V = 843.25 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.90 × 0.07 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.923, T_max = 0.995
4184 measured reflections
2275 independent reflections
2138 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.05
2275 reflections
222 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.91 (2)	2.27 (1)	3.0918 (17)	149 (2)
C1—H1⋯O3ⁱⁱ	1.00	2.55	3.503 (2)	160
C19—H19B⋯O2ⁱⁱⁱ	0.98	2.53	3.270 (2)	132
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (ii) x, y+1, z; (iii) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018782/is2714sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018782/is2714Isup2.hkl

checkCIF report

Comment top

The title compound is a novel chiral organocatalyst containing a tetrahydroisoquinoline (TIQ) framework. We have recently reported the use of similar TIQ derivatives as organocatalysts in the Diels-Alder cycloaddition between alpha, beta-unsaturated aldehydes and cyclopentadiene (Naicker et al., 2010).

Diastereomers formed during the synthesis of the title compound were easily separated using column chromatography to yield the TIQ derivative with the stereochemistry as illustrated in Fig. 1. The absolute stereochemistry was confirmed to be S,S at the C1 and C9 positions, respectively, by proton NMR spectroscopy.

The N-containing six-membered ring assumes a half-boat conformation [Q = 0.5537 (16) Å, θ = 53.94 (16)° and ϕ = 335.3 (2)°]. This observation is similar to a related structure that we recently reported (Naicker et al., 2011). The molecules are linked through N1— H1N···O3ⁱ and C1—H1···O3ⁱⁱ hydrogen bonds (Table 1) into a column stacked along the b axis. The columns are further connected by C19—H19B···O2ⁱⁱⁱ hydrogen bonds, forming a layer parallel to the (101) plane (Fig. 2).

Related literature top

For related structures, see: Naicker et al. (2010, 2011).

Experimental top

To a stirred solution of 1:1 methanol: methylene chloride (6.0 ml) with 4 Å molecular sieves, (S)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate (1.0 g, 4.2 mmol) and benzaldehdye (1.1 eq.) was added under an inert atmosphere. The reaction mixture was allowed to stir for 1.5 h. Thereafter the reaction mixture was filtered and the solvents was removed in vacuo to yield the intermediate imine which was left on a high vacuum pump to remove any residual water for 2 h. The residue was then dissolved in trifluoroacetic acid (20 ml) and refluxed for 3 h. The reaction mixture was then neutralized with a saturated sodium bicarbonate solution and extracted with ethylacetate (4 × 20 ml). The organic extracts were combined and dried over anhydrous Na₂SO₄ and the solvent was removed in vacuo. The crude product (diastereomers) was purified by column chromatography (50:50 EtOAc/Hexane, R_f 1/2) to afford the product 1.20 g (88%) as a white solid. Melting point 370–372 K. IR (neat): 2928, 2600, 1746, 1516, 1250, 1123, 727 cm^-1 [α]²⁰_D = +15.38 (c 0.26 in CHCl₃) ¹H NMR (400 MHz, CDCl₃) δ 7.33 – 7.11 (m, 5H), 6.57 (s, 1H), 6.10 (s, 1H), 5.02 (s, 1H), 3.79 (s, 4H), 3.70 (s, 3H), 3.52 (s, 3H), 3.01 (s, 2H). ¹³C NMR (101 MHz, CDCl₃) δ 172.96, 147.76, 147.41, 143.87, 130.22, 129.04, 128.59, 127.84, 126.07, 111.31, 110.56, 62.85, 56.54, 55.89, 55.84, 52.18, 32.22.

Recrystallization from ethyl acetate at room temperature afforded crystals suitable for X-ray analysis.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. A partial projection of the title compound, viewed along the a axis.

(1S,3S)-Methyl 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate top

Crystal data top

C₁₉H₂₁NO₄	F(000) = 348
M_r = 327.37	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁	Melting point: 371 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.3841 (3) Å	Cell parameters from 4184 reflections
b = 6.3453 (2) Å	θ = 2.2–28.3°
c = 14.2048 (4) Å	µ = 0.09 mm⁻¹
β = 94.475 (2)°	T = 173 K
V = 843.25 (4) Å³	Needle, colourless
Z = 2	0.90 × 0.07 × 0.06 mm

Data collection top

Nonius KappaCCD diffractometer	2275 independent reflections
Radiation source: fine-focus sealed tube	2138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.923, T_max = 0.995	k = −8→8
4184 measured reflections	l = −18→18

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0478P)² + 0.1004P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2275 reflections	Δρ_max = 0.20 e Å⁻³
222 parameters	Δρ_min = −0.13 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₁₉H₂₁NO₄	V = 843.25 (4) Å³
M_r = 327.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.3841 (3) Å	µ = 0.09 mm⁻¹
b = 6.3453 (2) Å	T = 173 K
c = 14.2048 (4) Å	0.90 × 0.07 × 0.06 mm
β = 94.475 (2)°

Data collection top

Nonius KappaCCD diffractometer	2275 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2138 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.995	R_int = 0.010
4184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	2 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.20 e Å⁻³
2275 reflections	Δρ_min = −0.13 e Å⁻³
222 parameters

Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 33 mm; combination of ϕ and ω scans of 1.0°, 60 s per °, 2 iterations.

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	0.32761 (13)	0.8193 (2)	0.52227 (9)	0.0421 (3)
O2	0.14691 (13)	0.5304 (2)	0.46573 (8)	0.0377 (3)
O3	0.39059 (11)	−0.1210 (2)	0.96117 (8)	0.0372 (3)
O4	0.15273 (11)	−0.0802 (2)	0.93763 (8)	0.0359 (3)
N1	0.44475 (13)	0.2219 (2)	0.85516 (9)	0.0286 (3)
H1N	0.4969 (18)	0.214 (4)	0.9118 (11)	0.033 (5)*
C1	0.45806 (15)	0.4396 (3)	0.82212 (10)	0.0276 (3)
H1	0.4271	0.5382	0.8715	0.033*
C2	0.36095 (14)	0.4684 (2)	0.73185 (10)	0.0260 (3)
C3	0.38575 (16)	0.6398 (3)	0.67243 (11)	0.0303 (3)
H3	0.4558	0.7420	0.6921	0.036*
C4	0.30923 (16)	0.6610 (3)	0.58571 (11)	0.0309 (3)
C5	0.20784 (15)	0.5077 (3)	0.55602 (10)	0.0299 (3)
C6	0.17693 (14)	0.3466 (3)	0.61690 (10)	0.0273 (3)
H6	0.1036	0.2485	0.5984	0.033*
C7	0.25316 (14)	0.3266 (2)	0.70613 (10)	0.0250 (3)
C8	0.21706 (15)	0.1462 (3)	0.76978 (10)	0.0274 (3)
H8A	0.2446	0.0110	0.7415	0.033*
H8B	0.1127	0.1433	0.7759	0.033*
C9	0.29613 (15)	0.1715 (3)	0.86760 (10)	0.0259 (3)
H9	0.2524	0.2909	0.9011	0.031*
C10	0.28876 (15)	−0.0258 (3)	0.92677 (10)	0.0273 (3)
C11	0.1344 (2)	−0.2585 (3)	0.99879 (13)	0.0423 (4)
H11A	0.0322	−0.2859	1.0025	0.063*
H11B	0.1788	−0.2277	1.0621	0.063*
H11C	0.1799	−0.3829	0.9733	0.063*
C12	0.61296 (15)	0.4843 (3)	0.80537 (10)	0.0291 (3)
C13	0.68782 (16)	0.3487 (3)	0.74980 (11)	0.0374 (4)
H13	0.6419	0.2270	0.7229	0.045*
C14	0.82974 (17)	0.3906 (4)	0.73342 (12)	0.0426 (4)
H14	0.8798	0.2980	0.6951	0.051*
C15	0.89763 (17)	0.5663 (4)	0.77280 (13)	0.0431 (4)
H15	0.9951	0.5924	0.7631	0.052*
C16	0.82347 (18)	0.7041 (3)	0.82631 (13)	0.0419 (4)
H16	0.8695	0.8269	0.8520	0.050*
C17	0.68109 (16)	0.6639 (3)	0.84278 (11)	0.0339 (3)
H17	0.6307	0.7594	0.8796	0.041*
C18	0.43336 (19)	0.9743 (3)	0.54802 (15)	0.0450 (4)
H18A	0.4362	1.0782	0.4972	0.067*
H18B	0.5270	0.9062	0.5585	0.067*
H18C	0.4097	1.0450	0.6061	0.067*
C19	0.0553 (2)	0.3649 (3)	0.43094 (12)	0.0480 (5)
H19A	0.0173	0.3981	0.3664	0.072*
H19B	−0.0238	0.3498	0.4715	0.072*
H19C	0.1094	0.2328	0.4308	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0381 (6)	0.0362 (7)	0.0523 (7)	−0.0028 (6)	0.0043 (5)	0.0163 (6)
O2	0.0426 (6)	0.0405 (7)	0.0296 (5)	−0.0005 (6)	−0.0009 (4)	0.0067 (5)
O3	0.0353 (6)	0.0404 (7)	0.0356 (6)	0.0093 (6)	0.0002 (4)	0.0060 (5)
O4	0.0313 (5)	0.0380 (7)	0.0380 (6)	−0.0025 (5)	−0.0002 (4)	0.0088 (5)
N1	0.0229 (6)	0.0322 (7)	0.0299 (6)	0.0000 (5)	−0.0032 (5)	0.0002 (6)
C1	0.0234 (6)	0.0302 (8)	0.0290 (7)	−0.0003 (6)	0.0007 (5)	−0.0056 (6)
C2	0.0214 (6)	0.0254 (7)	0.0315 (7)	0.0018 (6)	0.0031 (5)	−0.0026 (6)
C3	0.0237 (6)	0.0251 (7)	0.0422 (8)	0.0006 (6)	0.0023 (5)	−0.0008 (7)
C4	0.0263 (6)	0.0281 (8)	0.0390 (8)	0.0036 (6)	0.0077 (6)	0.0067 (7)
C5	0.0266 (7)	0.0337 (8)	0.0296 (7)	0.0040 (6)	0.0030 (5)	0.0018 (6)
C6	0.0237 (6)	0.0286 (7)	0.0296 (7)	0.0000 (6)	0.0012 (5)	−0.0001 (6)
C7	0.0218 (6)	0.0257 (7)	0.0276 (6)	0.0017 (6)	0.0027 (5)	−0.0004 (6)
C8	0.0243 (6)	0.0284 (7)	0.0289 (7)	−0.0023 (6)	−0.0012 (5)	0.0021 (6)
C9	0.0240 (6)	0.0271 (7)	0.0267 (6)	0.0021 (6)	0.0017 (5)	−0.0016 (6)
C10	0.0302 (7)	0.0291 (8)	0.0223 (6)	0.0015 (6)	0.0008 (5)	−0.0040 (6)
C11	0.0477 (9)	0.0388 (10)	0.0404 (9)	−0.0081 (8)	0.0035 (7)	0.0082 (8)
C12	0.0232 (6)	0.0350 (8)	0.0284 (7)	−0.0005 (6)	−0.0017 (5)	−0.0012 (6)
C13	0.0290 (7)	0.0449 (10)	0.0381 (8)	0.0022 (8)	0.0010 (6)	−0.0077 (8)
C14	0.0299 (7)	0.0590 (12)	0.0394 (8)	0.0068 (8)	0.0068 (6)	−0.0014 (9)
C15	0.0247 (7)	0.0602 (12)	0.0445 (9)	−0.0010 (8)	0.0029 (6)	0.0106 (9)
C16	0.0314 (8)	0.0473 (11)	0.0460 (9)	−0.0093 (8)	−0.0031 (7)	0.0041 (9)
C17	0.0286 (7)	0.0370 (9)	0.0357 (8)	−0.0045 (7)	0.0002 (6)	−0.0014 (7)
C18	0.0414 (9)	0.0287 (9)	0.0673 (12)	−0.0008 (8)	0.0203 (8)	0.0072 (9)
C19	0.0671 (12)	0.0411 (11)	0.0331 (8)	0.0001 (10)	−0.0126 (8)	0.0006 (8)

Geometric parameters (Å, º) top

O1—C4	1.3696 (19)	C8—H8B	0.9900
O1—C18	1.424 (2)	C9—C10	1.512 (2)
O2—C5	1.3704 (18)	C9—H9	1.0000
O2—C19	1.421 (2)	C11—H11A	0.9800
O3—C10	1.2017 (18)	C11—H11B	0.9800
O4—C10	1.3429 (18)	C11—H11C	0.9800
O4—C11	1.445 (2)	C12—C17	1.392 (2)
N1—C9	1.4552 (18)	C12—C13	1.394 (2)
N1—C1	1.467 (2)	C13—C14	1.395 (2)
N1—H1N	0.909 (14)	C13—H13	0.9500
C1—C12	1.5178 (19)	C14—C15	1.380 (3)
C1—C2	1.525 (2)	C14—H14	0.9500
C1—H1	1.0000	C15—C16	1.382 (3)
C2—C7	1.381 (2)	C15—H15	0.9500
C2—C3	1.407 (2)	C16—C17	1.398 (2)
C3—C4	1.383 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.403 (2)	C18—H18A	0.9800
C5—C6	1.384 (2)	C18—H18B	0.9800
C6—C7	1.4118 (18)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.513 (2)	C19—H19B	0.9800
C8—C9	1.5317 (19)	C19—H19C	0.9800
C8—H8A	0.9900

C4—O1—C18	117.28 (14)	C8—C9—H9	108.9
C5—O2—C19	116.41 (13)	O3—C10—O4	123.84 (15)
C10—O4—C11	115.40 (13)	O3—C10—C9	124.95 (14)
C9—N1—C1	110.63 (12)	O4—C10—C9	111.20 (12)
C9—N1—H1N	109.5 (12)	O4—C11—H11A	109.5
C1—N1—H1N	106.5 (15)	O4—C11—H11B	109.5
N1—C1—C12	109.42 (13)	H11A—C11—H11B	109.5
N1—C1—C2	108.75 (12)	O4—C11—H11C	109.5
C12—C1—C2	111.26 (12)	H11A—C11—H11C	109.5
N1—C1—H1	109.1	H11B—C11—H11C	109.5
C12—C1—H1	109.1	C17—C12—C13	119.00 (14)
C2—C1—H1	109.1	C17—C12—C1	120.67 (14)
C7—C2—C3	119.79 (13)	C13—C12—C1	120.31 (14)
C7—C2—C1	121.43 (13)	C12—C13—C14	120.43 (18)
C3—C2—C1	118.75 (13)	C12—C13—H13	119.8
C4—C3—C2	120.72 (14)	C14—C13—H13	119.8
C4—C3—H3	119.6	C15—C14—C13	120.18 (18)
C2—C3—H3	119.6	C15—C14—H14	119.9
O1—C4—C3	125.04 (15)	C13—C14—H14	119.9
O1—C4—C5	115.36 (14)	C14—C15—C16	119.84 (16)
C3—C4—C5	119.55 (14)	C14—C15—H15	120.1
O2—C5—C6	124.75 (14)	C16—C15—H15	120.1
O2—C5—C4	115.61 (14)	C15—C16—C17	120.37 (18)
C6—C5—C4	119.64 (13)	C15—C16—H16	119.8
C5—C6—C7	120.76 (14)	C17—C16—H16	119.8
C5—C6—H6	119.6	C12—C17—C16	120.14 (16)
C7—C6—H6	119.6	C12—C17—H17	119.9
C2—C7—C6	119.20 (13)	C16—C17—H17	119.9
C2—C7—C8	121.88 (12)	O1—C18—H18A	109.5
C6—C7—C8	118.89 (13)	O1—C18—H18B	109.5
C7—C8—C9	110.34 (12)	H18A—C18—H18B	109.5
C7—C8—H8A	109.6	O1—C18—H18C	109.5
C9—C8—H8A	109.6	H18A—C18—H18C	109.5
C7—C8—H8B	109.6	H18B—C18—H18C	109.5
C9—C8—H8B	109.6	O2—C19—H19A	109.5
H8A—C8—H8B	108.1	O2—C19—H19B	109.5
N1—C9—C10	109.60 (12)	H19A—C19—H19B	109.5
N1—C9—C8	108.29 (11)	O2—C19—H19C	109.5
C10—C9—C8	112.19 (12)	H19A—C19—H19C	109.5
N1—C9—H9	108.9	H19B—C19—H19C	109.5
C10—C9—H9	108.9

C9—N1—C1—C12	−177.34 (12)	C5—C6—C7—C8	−179.14 (14)
C9—N1—C1—C2	−55.63 (14)	C2—C7—C8—C9	9.86 (19)
N1—C1—C2—C7	16.42 (18)	C6—C7—C8—C9	−171.91 (13)
C12—C1—C2—C7	137.00 (14)	C1—N1—C9—C10	−163.99 (11)
N1—C1—C2—C3	−161.44 (13)	C1—N1—C9—C8	73.33 (15)
C12—C1—C2—C3	−40.86 (19)	C7—C8—C9—N1	−46.80 (16)
C7—C2—C3—C4	−4.0 (2)	C7—C8—C9—C10	−167.89 (11)
C1—C2—C3—C4	173.89 (14)	C11—O4—C10—O3	3.2 (2)
C18—O1—C4—C3	−0.3 (2)	C11—O4—C10—C9	−175.80 (13)
C18—O1—C4—C5	−177.71 (14)	N1—C9—C10—O3	2.7 (2)
C2—C3—C4—O1	−178.59 (14)	C8—C9—C10—O3	123.00 (16)
C2—C3—C4—C5	−1.2 (2)	N1—C9—C10—O4	−178.38 (12)
C19—O2—C5—C6	−5.8 (2)	C8—C9—C10—O4	−58.05 (15)
C19—O2—C5—C4	173.61 (15)	N1—C1—C12—C17	−130.54 (15)
O1—C4—C5—O2	3.6 (2)	C2—C1—C12—C17	109.27 (16)
C3—C4—C5—O2	−174.04 (14)	N1—C1—C12—C13	51.37 (18)
O1—C4—C5—C6	−177.03 (13)	C2—C1—C12—C13	−68.82 (19)
C3—C4—C5—C6	5.4 (2)	C17—C12—C13—C14	1.2 (3)
O2—C5—C6—C7	175.00 (14)	C1—C12—C13—C14	179.29 (16)
C4—C5—C6—C7	−4.4 (2)	C12—C13—C14—C15	0.5 (3)
C3—C2—C7—C6	5.0 (2)	C13—C14—C15—C16	−1.9 (3)
C1—C2—C7—C6	−172.82 (13)	C14—C15—C16—C17	1.6 (3)
C3—C2—C7—C8	−176.77 (13)	C13—C12—C17—C16	−1.4 (2)
C1—C2—C7—C8	5.4 (2)	C1—C12—C17—C16	−179.55 (15)
C5—C6—C7—C2	−0.9 (2)	C15—C16—C17—C12	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.91 (2)	2.27 (1)	3.0918 (17)	149 (2)
C1—H1···O3ⁱⁱ	1.00	2.55	3.503 (2)	160
C19—H19B···O2ⁱⁱⁱ	0.98	2.53	3.270 (2)	132

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁NO₄
M_r	327.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	9.3841 (3), 6.3453 (2), 14.2048 (4)
β (°)	94.475 (2)
V (Å³)	843.25 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.90 × 0.07 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	4184, 2275, 2138
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.05
No. of reflections	2275
No. of parameters	222
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)	0.20, −0.13

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.910 (16)	2.2741 (18)	3.0918 (17)	149 (2)
C1—H1···O3ⁱⁱ	1.00	2.55	3.503 (2)	160
C19—H19B···O2ⁱⁱⁱ	0.98	2.53	3.270 (2)	132

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

Acknowledgements

The authors wish to thank Dr Hong Su from the Chemistry Department of the University of Cape Town for her assistance with the crystallographic data collection.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011). Acta Cryst. E67, o1403. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859–2867. Web of Science CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

(1S,3S)-Methyl 6,7-dimeth­­oxy-1-phenyl-1,2,3,4-tetra­hydro­iso­quinoline-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,3S)-Methyl 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate