(R)-4-Phenyl-2-[(S)-1,2,3,4-tetra-hydro-isoquinolin-3-yl]-4,5-dihydro-1,3-oxazole.

The asymmetric unit cell of the title compound, C(18)H(18)N(2)O, contains four molecules. In the crystal structure, an inter-molecular 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 = 278.34

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.05

1552 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

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.

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

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

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

C18H18N2O	F(000) = 592
Mr = 278.34	Dx = 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

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

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(Fo2) + (0.0436P)2 + 0.1838P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1552 reflections	Δρmax = 0.14 e Å−3
195 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .