(R)-4-Phenyl-2-[(S)-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4,5-dihydro-1,3-oxazole

Chakka, S.K.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536810022130

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1818

doi:10.1107/S1600536810022130

Open

access

(R)-4-Phenyl-2-[(S)-1,2,3,4-tetrahydroisoquinolin-3-yl]-4,5-dihydro-1,3-oxazole

Sai K. Chakka,^a Thavendran Govender,^b Hendrik G. Kruger ^a and Glenn E. M. Maguire ^a ^*

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

(Received 27 May 2010; accepted 9 June 2010; online 26 June 2010)

The asymmetric unit cell of the title compound, C₁₈H₁₈N₂O, contains four molecules. In the crystal structure, an intermolecular N—H⋯N hydrogen bond helps to establish the packing.

Related literature

For the assymetric synthetic applications of oxazoline, see: Hargaden et al. (2009 ). For tetraisoquinolines and their biological significance, see: Scott et al. (2002 ). For ligand catalysis activity, see: Chakka et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₈N₂O
M_r = 278.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4023 (3) Å
b = 10.0999 (6) Å
c = 26.2205 (17) Å
V = 1430.66 (15) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 173 K
0.22 × 0.21 × 0.10 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.682, T_max = 0.753
6634 measured reflections
1552 independent reflections
1479 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.076
S = 1.05
1552 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.96 (1)	2.20 (1)	3.139 (2)	165 (2)
Symmetry code: (i) x+1, y, z.

Data collection: SAINT (Bruker, 2006 ); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022130/hg2694sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022130/hg2694Isup2.hkl

checkCIF report

Comment top

Heterocyclic rings play roles in a number of key areas of organic and inorganic chemistry. As part of an ongoing study into the asymmetric hydrogen transfer reactions we made a series of ligands (Chakka et al., 2010). The title compound (I) is one such molecule (Fig 1). It combines for the first time two important heterocyclic rings into a single structure, namely oxazoline (Hargaden et al., 2009) and tetraisoquinoline (TIQ), (Scott et al., 2002). The asymmetric unit cell contains four molecules. There are inter-molecular N(1)—H···N(1) bond interactions (2.212 Å) that hold the structure in two dimensional planes. The intermolecular distance value between ring centroids in the b axis direction (5.402 Å), suggests that there is no π-stacking interaction between parallel molecules (Fig 2).

Related literature top

For the assymetric synthetic applications of oxazoline, see: Hargaden et al. (2009). For tetraisoquinolines and their biological significance, see: Scott et al. (2002). For ligand catalysis activity, see: Chakka et al. (2010).

Experimental top

A solution of Cbz-protected TIQ–oxazoline (1.0 g, 2.89 mmol) in methanol (30 ml) was added to a suspension of 10 wt.% Pd/C (0.5 g) in methanol (10 ml). The reaction mixture was connected to an H₂ source at atmospheric pressure and stirred at room temperature for 3 h. Completion of the reaction was monitored by TLC using hexane/ethyl acetate (7:3) with the R_f= 0.6. The Pd/C was filtered off over a celite pad and the filtrate was concentrated under reduced pressure to afford crude (I). The title compound was purified on a deactivated silica gel column packed with a suspension of silica gel in 20% Et₃N/CH₂Cl₂. The silica was washed with 1% Et₃N/CH₂Cl₂. The chromatography was then performed using 0–2% MeOH/1%Et₃N/CH₂Cl₂ as the eluent to afford TIQ-oxazoline product. M.p: 304 – 306 K.

¹H NMR (400 MHz, CDCl₃): δ 7.37–7.23 (m, 3H), 7.23–7.10 (m, 5H), 7.05 (m, 1H), 5.23 (t, J = 18.21 Hz, 1H), 4.68 (q, J = 10.10, 8.26 Hz, 1H), 4.16 (m, 3H), 3.92 (m, 1H), 3.10–3.05 (m, 2H); ¹³C NMR (100 MHz, CDCl₃): δ 168.9, 142.0, 135.0, 133.3, 129.2, 128.7, 127.6, 126.5, 126.2, 126.1, 126.0, 69.4, 51.5, 47.6, 32.4.

IR (neat): 3225, 1663, 1493, 1108, 957, 907, 916, 740, 749, 697 cm^-1.

HR ESI MS: 279.1492 [M + H]⁺ (calcd. for C₁₈H₁₉N₂O 279.1512).

Computing details top

Data collection: SAINT (Bruker, 2006); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) showing numbering scheme. All non-hydrogen atoms are shown as ellipsoids with probability level of 50%.
	Fig. 2. Projection viewed along [010]. All hydrogen atoms except the hydrogen H1N on N1 are omitted. The hydrogen bonds are shown as dotted lines.

(R)-4-Phenyl-2-[(S)-1,2,3,4-tetrahydroisoquinolin-3-yl]-4,5- dihydro-1,3-oxazole top

Crystal data top

C₁₈H₁₈N₂O	F(000) = 592
M_r = 278.34	D_x = 1.292 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6634 reflections
a = 5.4023 (3) Å	θ = 4.7–69.2°
b = 10.0999 (6) Å	µ = 0.64 mm⁻¹
c = 26.2205 (17) Å	T = 173 K
V = 1430.66 (15) Å³	Needle, colourless
Z = 4	0.22 × 0.21 × 0.10 mm

Data collection top

Bruker Kappa DUO APEXII diffractometer	1552 independent reflections
Radiation source: fine-focus sealed tube	1479 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: n/a pixels mm^-1	θ_max = 69.2°, θ_min = 4.7°
0.5° ϕ scans and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	k = −11→12
T_min = 0.682, T_max = 0.753	l = −15→30
6634 measured reflections

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) = 0.076	w = 1/[σ²(F_o²) + (0.0436P)² + 0.1838P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1552 reflections	Δρ_max = 0.14 e Å⁻³
195 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (5)

Crystal data top

C₁₈H₁₈N₂O	V = 1430.66 (15) Å³
M_r = 278.34	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.4023 (3) Å	µ = 0.64 mm⁻¹
b = 10.0999 (6) Å	T = 173 K
c = 26.2205 (17) Å	0.22 × 0.21 × 0.10 mm

Data collection top

Bruker Kappa DUO APEXII diffractometer	1552 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1479 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.753	R_int = 0.036
6634 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.14 e Å⁻³
1552 reflections	Δρ_min = −0.12 e Å⁻³
195 parameters

Special details top

Experimental. Half sphere of data collected using SAINT strategy (Bruker, 2006). Crystal to detector distance = 50 mm; combination of ϕ and ω scans of 0.5°, 30 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	0.4184 (2)	0.79986 (13)	0.19408 (5)	0.0306 (3)
N1	0.5780 (3)	1.06125 (15)	0.15598 (6)	0.0272 (3)
H1N	0.702 (3)	1.0028 (18)	0.1694 (7)	0.033 (6)*
N2	0.0533 (3)	0.90911 (15)	0.19216 (6)	0.0285 (4)
C1	0.6813 (4)	1.15005 (18)	0.11756 (7)	0.0324 (4)
H1A	0.8214	1.1991	0.1329	0.039*
H1B	0.5533	1.2157	0.1080	0.039*
C2	0.7714 (3)	1.08180 (18)	0.06969 (7)	0.0269 (4)
C3	0.9535 (4)	1.13952 (18)	0.03901 (7)	0.0322 (4)
H3	1.0184	1.2238	0.0480	0.039*
C4	1.0408 (4)	1.0762 (2)	−0.00419 (7)	0.0363 (5)
H4	1.1656	1.1162	−0.0245	0.044*
C5	0.9444 (4)	0.9538 (2)	−0.01748 (7)	0.0382 (5)
H5	1.0025	0.9096	−0.0471	0.046*
C6	0.7634 (4)	0.89605 (19)	0.01249 (7)	0.0356 (5)
H6	0.6978	0.8123	0.0031	0.043*
C7	0.6755 (4)	0.95876 (18)	0.05633 (7)	0.0285 (4)
C8	0.4854 (4)	0.89025 (19)	0.08944 (7)	0.0350 (5)
H8A	0.5606	0.8097	0.1043	0.042*
H8B	0.3448	0.8621	0.0678	0.042*
C9	0.3869 (3)	0.97793 (18)	0.13282 (7)	0.0272 (4)
H9	0.2567	1.0374	0.1183	0.033*
C10	0.2691 (3)	0.89535 (18)	0.17416 (7)	0.0260 (4)
C11	0.2612 (3)	0.72424 (17)	0.22836 (7)	0.0279 (4)
H11A	0.3444	0.7089	0.2615	0.033*
H11B	0.2159	0.6378	0.2132	0.033*
C12	0.0312 (3)	0.81315 (17)	0.23493 (7)	0.0258 (4)
H12	−0.1226	0.7592	0.2308	0.031*
C13	0.0251 (3)	0.88531 (17)	0.28547 (6)	0.0247 (4)
C14	−0.1619 (3)	0.86228 (18)	0.32043 (7)	0.0288 (4)
H14	−0.2902	0.8014	0.3124	0.035*
C15	−0.1639 (4)	0.92738 (19)	0.36719 (7)	0.0327 (4)
H15	−0.2932	0.9106	0.3909	0.039*
C16	0.0209 (4)	1.01606 (19)	0.37932 (7)	0.0329 (4)
H16	0.0188	1.0608	0.4112	0.040*
C17	0.2105 (4)	1.03964 (19)	0.34458 (7)	0.0330 (4)
H17	0.3394	1.0999	0.3528	0.040*
C18	0.2114 (3)	0.97527 (18)	0.29802 (7)	0.0290 (4)
H18	0.3403	0.9925	0.2743	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (6)	0.0313 (6)	0.0336 (7)	0.0056 (6)	0.0025 (5)	0.0064 (5)
N1	0.0279 (7)	0.0272 (7)	0.0267 (7)	0.0012 (7)	0.0002 (6)	−0.0021 (6)
N2	0.0249 (7)	0.0349 (8)	0.0257 (7)	0.0035 (7)	−0.0025 (6)	0.0027 (7)
C1	0.0363 (11)	0.0260 (8)	0.0349 (10)	−0.0015 (8)	0.0026 (8)	−0.0034 (8)
C2	0.0281 (9)	0.0266 (8)	0.0260 (8)	0.0031 (8)	−0.0035 (7)	0.0029 (7)
C3	0.0335 (10)	0.0292 (9)	0.0338 (10)	−0.0020 (8)	−0.0014 (8)	0.0045 (8)
C4	0.0385 (10)	0.0396 (10)	0.0309 (9)	0.0013 (10)	0.0044 (8)	0.0087 (8)
C5	0.0493 (12)	0.0387 (10)	0.0267 (9)	0.0046 (10)	0.0070 (9)	0.0009 (8)
C6	0.0488 (12)	0.0302 (9)	0.0279 (9)	−0.0025 (9)	0.0006 (8)	−0.0024 (7)
C7	0.0326 (9)	0.0291 (9)	0.0237 (8)	0.0016 (8)	−0.0018 (7)	0.0029 (7)
C8	0.0437 (12)	0.0335 (9)	0.0277 (9)	−0.0099 (9)	0.0030 (8)	−0.0035 (8)
C9	0.0253 (9)	0.0310 (9)	0.0252 (9)	0.0017 (8)	−0.0027 (7)	0.0016 (7)
C10	0.0260 (9)	0.0272 (8)	0.0247 (8)	0.0024 (8)	−0.0050 (7)	−0.0001 (7)
C11	0.0297 (9)	0.0262 (8)	0.0278 (9)	0.0022 (8)	0.0005 (7)	0.0006 (7)
C12	0.0227 (8)	0.0284 (8)	0.0262 (8)	0.0007 (7)	−0.0006 (7)	−0.0002 (8)
C13	0.0232 (8)	0.0245 (8)	0.0264 (8)	0.0045 (7)	−0.0024 (7)	0.0029 (7)
C14	0.0254 (9)	0.0281 (9)	0.0329 (10)	−0.0005 (8)	0.0017 (8)	0.0027 (7)
C15	0.0311 (10)	0.0358 (10)	0.0313 (9)	0.0013 (9)	0.0059 (8)	0.0021 (8)
C16	0.0360 (11)	0.0361 (9)	0.0267 (8)	0.0044 (9)	−0.0025 (8)	−0.0049 (8)
C17	0.0320 (9)	0.0301 (9)	0.0368 (10)	−0.0044 (8)	−0.0050 (8)	−0.0035 (8)
C18	0.0244 (9)	0.0310 (9)	0.0316 (9)	−0.0010 (8)	0.0011 (7)	0.0030 (8)

Geometric parameters (Å, º) top

O1—C10	1.362 (2)	C8—C9	1.537 (2)
O1—C11	1.454 (2)	C8—H8A	0.9900
N1—C1	1.460 (2)	C8—H8B	0.9900
N1—C9	1.464 (2)	C9—C10	1.508 (2)
N1—H1N	0.960 (10)	C9—H9	1.0000
N2—C10	1.265 (2)	C11—C12	1.542 (3)
N2—C12	1.487 (2)	C11—H11A	0.9900
C1—C2	1.513 (2)	C11—H11B	0.9900
C1—H1A	0.9900	C12—C13	1.513 (2)
C1—H1B	0.9900	C12—H12	1.0000
C2—C7	1.391 (3)	C13—C14	1.384 (2)
C2—C3	1.398 (3)	C13—C18	1.395 (3)
C3—C4	1.384 (3)	C14—C15	1.391 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.386 (3)	C15—C16	1.378 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.383 (3)	C16—C17	1.391 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.396 (3)	C17—C18	1.383 (3)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.512 (3)	C18—H18	0.9500

C10—O1—C11	105.26 (13)	C10—C9—C8	111.06 (15)
C1—N1—C9	109.66 (14)	N1—C9—H9	108.0
C1—N1—H1N	111.3 (13)	C10—C9—H9	108.0
C9—N1—H1N	106.9 (13)	C8—C9—H9	108.0
C10—N2—C12	106.47 (15)	N2—C10—O1	118.72 (17)
N1—C1—C2	114.56 (14)	N2—C10—C9	126.58 (17)
N1—C1—H1A	108.6	O1—C10—C9	114.67 (15)
C2—C1—H1A	108.6	O1—C11—C12	103.52 (14)
N1—C1—H1B	108.6	O1—C11—H11A	111.1
C2—C1—H1B	108.6	C12—C11—H11A	111.1
H1A—C1—H1B	107.6	O1—C11—H11B	111.1
C7—C2—C3	119.32 (17)	C12—C11—H11B	111.1
C7—C2—C1	119.75 (16)	H11A—C11—H11B	109.0
C3—C2—C1	120.92 (17)	N2—C12—C13	110.39 (13)
C4—C3—C2	121.21 (18)	N2—C12—C11	103.33 (14)
C4—C3—H3	119.4	C13—C12—C11	113.32 (14)
C2—C3—H3	119.4	N2—C12—H12	109.9
C3—C4—C5	119.33 (19)	C13—C12—H12	109.9
C3—C4—H4	120.3	C11—C12—H12	109.9
C5—C4—H4	120.3	C14—C13—C18	118.68 (17)
C6—C5—C4	119.93 (19)	C14—C13—C12	121.02 (16)
C6—C5—H5	120.0	C18—C13—C12	120.29 (15)
C4—C5—H5	120.0	C13—C14—C15	120.66 (17)
C5—C6—C7	121.13 (19)	C13—C14—H14	119.7
C5—C6—H6	119.4	C15—C14—H14	119.7
C7—C6—H6	119.4	C16—C15—C14	120.32 (18)
C2—C7—C6	119.08 (18)	C16—C15—H15	119.8
C2—C7—C8	121.13 (16)	C14—C15—H15	119.8
C6—C7—C8	119.76 (17)	C15—C16—C17	119.57 (17)
C7—C8—C9	113.36 (15)	C15—C16—H16	120.2
C7—C8—H8A	108.9	C17—C16—H16	120.2
C9—C8—H8A	108.9	C18—C17—C16	119.98 (18)
C7—C8—H8B	108.9	C18—C17—H17	120.0
C9—C8—H8B	108.9	C16—C17—H17	120.0
H8A—C8—H8B	107.7	C17—C18—C13	120.78 (17)
N1—C9—C10	108.50 (14)	C17—C18—H18	119.6
N1—C9—C8	113.21 (15)	C13—C18—H18	119.6

C9—N1—C1—C2	−52.7 (2)	C11—O1—C10—C9	−173.78 (14)
N1—C1—C2—C7	23.6 (3)	N1—C9—C10—N2	108.6 (2)
N1—C1—C2—C3	−155.27 (17)	C8—C9—C10—N2	−126.4 (2)
C7—C2—C3—C4	−0.4 (3)	N1—C9—C10—O1	−69.47 (19)
C1—C2—C3—C4	178.49 (18)	C8—C9—C10—O1	55.6 (2)
C2—C3—C4—C5	0.5 (3)	C10—O1—C11—C12	−14.48 (17)
C3—C4—C5—C6	−0.3 (3)	C10—N2—C12—C13	109.57 (16)
C4—C5—C6—C7	−0.2 (3)	C10—N2—C12—C11	−11.91 (18)
C3—C2—C7—C6	−0.1 (3)	O1—C11—C12—N2	15.96 (17)
C1—C2—C7—C6	−178.97 (17)	O1—C11—C12—C13	−103.52 (16)
C3—C2—C7—C8	177.66 (17)	N2—C12—C13—C14	127.42 (17)
C1—C2—C7—C8	−1.2 (3)	C11—C12—C13—C14	−117.22 (18)
C5—C6—C7—C2	0.4 (3)	N2—C12—C13—C18	−53.6 (2)
C5—C6—C7—C8	−177.41 (18)	C11—C12—C13—C18	61.8 (2)
C2—C7—C8—C9	8.5 (3)	C18—C13—C14—C15	−0.1 (3)
C6—C7—C8—C9	−173.72 (17)	C12—C13—C14—C15	178.90 (16)
C1—N1—C9—C10	−175.40 (15)	C13—C14—C15—C16	0.1 (3)
C1—N1—C9—C8	60.83 (19)	C14—C15—C16—C17	−0.3 (3)
C7—C8—C9—N1	−38.5 (2)	C15—C16—C17—C18	0.7 (3)
C7—C8—C9—C10	−160.89 (15)	C16—C17—C18—C13	−0.7 (3)
C12—N2—C10—O1	3.0 (2)	C14—C13—C18—C17	0.4 (3)
C12—N2—C10—C9	−174.98 (16)	C12—C13—C18—C17	−178.58 (17)
C11—O1—C10—N2	8.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.96 (1)	2.20 (1)	3.139 (2)	165 (2)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂O
M_r	278.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	5.4023 (3), 10.0999 (6), 26.2205 (17)
V (Å³)	1430.66 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.22 × 0.21 × 0.10

Data collection
Diffractometer	Bruker Kappa DUO APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.682, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	6634, 1552, 1479
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.05
No. of reflections	1552
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.12

Computer programs: SAINT (Bruker, 2006), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.960 (10)	2.203 (11)	3.139 (2)	164.8 (18)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors would like to thank Dr Hong Su (University of Cape Town) for the data collection and structure refinement.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakka, S. K., Andersson, P. G., Maguire, G. E. M., Kruger, H. G. & Govender, T. (2010). Eur. J. Org. Chem. pp. 972–980. Web of Science CrossRef Google Scholar
Hargaden, G. C. & Guiry, P. J. (2009). Chem. Rev. 109, 2505–2550. Web of Science CrossRef PubMed CAS 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
Scott, J. D. & Williams, R. M. (2002). Chem. Rev. 102, 1669–1730. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1997). 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1818

doi:10.1107/S1600536810022130

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(R)-4-Phenyl-2-[(S)-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4,5-di­hydro-1,3-oxazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(R)-4-Phenyl-2-[(S)-1,2,3,4-tetrahydroisoquinolin-3-yl]-4,5-dihydro-1,3-oxazole