1-[(Pyrrolidin-1-yl)(p-tol-yl)meth-yl]naphthalen-2-ol.

In the title compound, C(22)H(23)NO, the dihedral angle between the naphthyl ring system and the benzene ring is 73.32 (6)°. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal structure, mol-ecules are linked by C-H⋯π inter-actions, resulting in zigzag chains parallel to the [10] direction.

Related literature

For general background on the chemistry of naphthalen-2-ol derivatives, see: Szatmari & Fulop (2004 ▶); Zhao & Sun (2005 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C22H23NO

M = 317.41

Monoclinic,

a = 10.3467 (18) Å

b = 16.055 (3) Å

c = 11.252 (2) Å

β = 106.810 (8)°

V = 1789.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.25 × 0.22 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.989

18171 measured reflections

4086 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.190

S = 1.06

4086 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028493/rz2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028493/rz2244Isup2.hkl

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

C22H23NO	F(000) = 680
Mr = 317.41	Dx = 1.178 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3280 reflections
a = 10.3467 (18) Å	θ = 2.3–27.4°
b = 16.055 (3) Å	µ = 0.07 mm−1
c = 11.252 (2) Å	T = 293 K
β = 106.810 (8)°	Prism, colourless
V = 1789.2 (6) Å3	0.25 × 0.22 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	4086 independent reflections
Radiation source: fine-focus sealed tube	2547 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.963, Tmax = 0.989	l = −14→14
18171 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0911P)2 + 0.1709P] where P = (Fo2 + 2Fc2)/3
4086 reflections	(Δ/σ)max = 0.005
219 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
C1	0.2106 (2)	0.17738 (14)	0.94453 (19)	0.0419 (5)
C2	0.2318 (2)	0.10314 (14)	1.0087 (2)	0.0484 (6)
C3	0.3641 (2)	0.07349 (17)	1.0645 (2)	0.0593 (7)
H3	0.3762	0.0225	1.1056	0.071*
C4	0.4730 (2)	0.11799 (18)	1.0592 (2)	0.0603 (7)
H4	0.5591	0.0970	1.0959	0.072*
C5	0.4578 (2)	0.19606 (16)	0.9986 (2)	0.0511 (6)
C6	0.3253 (2)	0.22609 (14)	0.9413 (2)	0.0437 (5)
C7	0.3143 (2)	0.30541 (15)	0.8828 (2)	0.0526 (6)
H7	0.2292	0.3276	0.8455	0.063*
C8	0.4263 (3)	0.34974 (18)	0.8801 (3)	0.0680 (8)
H8	0.4161	0.4014	0.8410	0.082*
C9	0.5550 (3)	0.3189 (2)	0.9349 (3)	0.0713 (8)
H9	0.6302	0.3495	0.9317	0.086*
C10	0.5714 (2)	0.2439 (2)	0.9932 (3)	0.0654 (8)
H10	0.6579	0.2236	1.0299	0.078*
C11	0.0689 (2)	0.20844 (12)	0.87783 (19)	0.0396 (5)
H11	0.0738	0.2388	0.8037	0.048*
C12	0.0091 (2)	0.08850 (15)	0.7372 (2)	0.0512 (6)
H12A	0.0886	0.0544	0.7710	0.061*
H12B	0.0248	0.1249	0.6740	0.061*
C13	−0.1145 (2)	0.03501 (16)	0.6848 (2)	0.0603 (7)
H13A	−0.1071	−0.0171	0.7298	0.072*
H13B	−0.1269	0.0231	0.5977	0.072*
C14	−0.2303 (2)	0.08716 (16)	0.7016 (3)	0.0617 (7)
H14A	−0.2831	0.0555	0.7445	0.074*
H14B	−0.2890	0.1048	0.6218	0.074*
C15	−0.1655 (2)	0.16206 (16)	0.7785 (2)	0.0563 (7)
H15A	−0.1704	0.2107	0.7263	0.068*
H15B	−0.2098	0.1745	0.8415	0.068*
C16	0.01458 (19)	0.26802 (13)	0.95666 (19)	0.0395 (5)
C17	0.0117 (2)	0.24824 (14)	1.0757 (2)	0.0477 (5)
H17	0.0454	0.1972	1.1100	0.057*
C18	−0.0407 (2)	0.30347 (15)	1.1441 (2)	0.0528 (6)
H18	−0.0428	0.2884	1.2233	0.063*
C19	−0.0899 (2)	0.38058 (15)	1.0975 (2)	0.0479 (6)
C20	−0.0865 (2)	0.39997 (14)	0.9788 (2)	0.0493 (6)
H20	−0.1189	0.4514	0.9450	0.059*
C21	−0.0361 (2)	0.34482 (14)	0.9096 (2)	0.0458 (5)
H21	−0.0362	0.3595	0.8296	0.055*
C22	−0.1439 (3)	0.44099 (18)	1.1736 (3)	0.0712 (8)
H22A	−0.1290	0.4193	1.2560	0.107*
H22B	−0.2389	0.4488	1.1358	0.107*
H22C	−0.0982	0.4934	1.1776	0.107*
N1	−0.02391 (16)	0.13698 (11)	0.83579 (16)	0.0414 (4)
O1	0.13049 (17)	0.05359 (11)	1.02090 (17)	0.0641 (5)
H1	0.0585	0.0700	0.9744	0.096*

	U11	U22	U33	U12	U13	U23
C1	0.0345 (11)	0.0496 (13)	0.0407 (12)	−0.0007 (9)	0.0094 (9)	−0.0015 (9)
C2	0.0431 (12)	0.0535 (14)	0.0463 (13)	−0.0024 (10)	0.0091 (10)	0.0064 (10)
C3	0.0518 (14)	0.0671 (17)	0.0532 (15)	0.0093 (13)	0.0057 (12)	0.0106 (12)
C4	0.0392 (12)	0.0837 (19)	0.0513 (15)	0.0098 (12)	0.0024 (11)	−0.0049 (13)
C5	0.0368 (11)	0.0684 (16)	0.0465 (13)	−0.0041 (11)	0.0097 (10)	−0.0150 (11)
C6	0.0373 (11)	0.0525 (13)	0.0425 (12)	−0.0048 (9)	0.0135 (9)	−0.0096 (10)
C7	0.0464 (13)	0.0510 (14)	0.0629 (16)	−0.0094 (11)	0.0197 (11)	−0.0057 (11)
C8	0.0629 (17)	0.0617 (17)	0.086 (2)	−0.0203 (13)	0.0317 (15)	−0.0078 (14)
C9	0.0527 (16)	0.085 (2)	0.081 (2)	−0.0297 (15)	0.0271 (15)	−0.0208 (16)
C10	0.0368 (12)	0.094 (2)	0.0635 (17)	−0.0096 (13)	0.0123 (12)	−0.0234 (15)
C11	0.0361 (10)	0.0415 (12)	0.0407 (12)	−0.0038 (9)	0.0103 (9)	0.0045 (9)
C12	0.0431 (12)	0.0561 (15)	0.0543 (14)	−0.0004 (10)	0.0143 (11)	−0.0072 (11)
C13	0.0517 (14)	0.0602 (16)	0.0629 (16)	−0.0037 (12)	0.0070 (12)	−0.0137 (12)
C14	0.0407 (12)	0.0626 (16)	0.0748 (18)	−0.0043 (11)	0.0055 (12)	−0.0118 (13)
C15	0.0343 (12)	0.0621 (16)	0.0671 (16)	0.0008 (10)	0.0062 (11)	−0.0113 (12)
C16	0.0313 (10)	0.0451 (12)	0.0409 (12)	−0.0050 (9)	0.0086 (9)	0.0021 (9)
C17	0.0527 (13)	0.0446 (13)	0.0473 (13)	0.0006 (10)	0.0168 (11)	0.0070 (10)
C18	0.0560 (14)	0.0626 (16)	0.0433 (13)	−0.0062 (12)	0.0198 (11)	0.0010 (11)
C19	0.0335 (11)	0.0544 (14)	0.0543 (15)	−0.0033 (10)	0.0105 (10)	−0.0063 (11)
C20	0.0415 (12)	0.0446 (13)	0.0584 (15)	0.0059 (10)	0.0088 (11)	0.0044 (10)
C21	0.0411 (11)	0.0499 (14)	0.0440 (13)	0.0009 (10)	0.0085 (10)	0.0067 (10)
C22	0.0627 (17)	0.077 (2)	0.0782 (19)	0.0021 (14)	0.0275 (15)	−0.0171 (15)
N1	0.0309 (9)	0.0458 (10)	0.0463 (11)	−0.0024 (7)	0.0093 (8)	−0.0028 (8)
O1	0.0508 (10)	0.0634 (12)	0.0733 (13)	−0.0053 (8)	0.0102 (9)	0.0243 (9)

C1—C2	1.378 (3)	C12—H12B	0.9700
C1—C6	1.430 (3)	C13—C14	1.518 (3)
C1—C11	1.525 (3)	C13—H13A	0.9700
C2—O1	1.354 (3)	C13—H13B	0.9700
C2—C3	1.413 (3)	C14—C15	1.519 (3)
C3—C4	1.351 (4)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.414 (4)	C15—N1	1.476 (3)
C4—H4	0.9300	C15—H15A	0.9700
C5—C10	1.420 (3)	C15—H15B	0.9700
C5—C6	1.420 (3)	C16—C21	1.384 (3)
C6—C7	1.423 (3)	C16—C17	1.385 (3)
C7—C8	1.367 (3)	C17—C18	1.383 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.387 (4)	C18—C19	1.383 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.357 (4)	C19—C20	1.381 (3)
C9—H9	0.9300	C19—C22	1.504 (3)
C10—H10	0.9300	C20—C21	1.378 (3)
C11—N1	1.483 (2)	C20—H20	0.9300
C11—C16	1.518 (3)	C21—H21	0.9300
C11—H11	0.9800	C22—H22A	0.9600
C12—N1	1.474 (3)	C22—H22B	0.9600
C12—C13	1.511 (3)	C22—H22C	0.9600
C12—H12A	0.9700	O1—H1	0.8200
C2—C1—C6	118.6 (2)	C14—C13—H13A	110.9
C2—C1—C11	121.71 (19)	C12—C13—H13B	110.9
C6—C1—C11	119.71 (19)	C14—C13—H13B	110.9
O1—C2—C1	123.4 (2)	H13A—C13—H13B	108.9
O1—C2—C3	115.8 (2)	C13—C14—C15	105.88 (19)
C1—C2—C3	120.8 (2)	C13—C14—H14A	110.6
C4—C3—C2	121.0 (2)	C15—C14—H14A	110.6
C4—C3—H3	119.5	C13—C14—H14B	110.6
C2—C3—H3	119.5	C15—C14—H14B	110.6
C3—C4—C5	120.8 (2)	H14A—C14—H14B	108.7
C3—C4—H4	119.6	N1—C15—C14	104.57 (18)
C5—C4—H4	119.6	N1—C15—H15A	110.8
C4—C5—C10	121.5 (2)	C14—C15—H15A	110.8
C4—C5—C6	118.6 (2)	N1—C15—H15B	110.8
C10—C5—C6	120.0 (3)	C14—C15—H15B	110.8
C5—C6—C7	116.8 (2)	H15A—C15—H15B	108.9
C5—C6—C1	120.2 (2)	C21—C16—C17	117.6 (2)
C7—C6—C1	123.0 (2)	C21—C16—C11	120.06 (19)
C8—C7—C6	121.4 (2)	C17—C16—C11	122.37 (19)
C8—C7—H7	119.3	C18—C17—C16	120.8 (2)
C6—C7—H7	119.3	C18—C17—H17	119.6
C7—C8—C9	121.0 (3)	C16—C17—H17	119.6
C7—C8—H8	119.5	C19—C18—C17	121.6 (2)
C9—C8—H8	119.5	C19—C18—H18	119.2
C10—C9—C8	120.1 (2)	C17—C18—H18	119.2
C10—C9—H9	120.0	C20—C19—C18	117.3 (2)
C8—C9—H9	120.0	C20—C19—C22	121.5 (2)
C9—C10—C5	120.7 (3)	C18—C19—C22	121.2 (2)
C9—C10—H10	119.6	C21—C20—C19	121.4 (2)
C5—C10—H10	119.6	C21—C20—H20	119.3
N1—C11—C16	111.04 (16)	C19—C20—H20	119.3
N1—C11—C1	110.22 (16)	C20—C21—C16	121.3 (2)
C16—C11—C1	112.58 (17)	C20—C21—H21	119.4
N1—C11—H11	107.6	C16—C21—H21	119.4
C16—C11—H11	107.6	C19—C22—H22A	109.5
C1—C11—H11	107.6	C19—C22—H22B	109.5
N1—C12—C13	103.87 (18)	H22A—C22—H22B	109.5
N1—C12—H12A	111.0	C19—C22—H22C	109.5
C13—C12—H12A	111.0	H22A—C22—H22C	109.5
N1—C12—H12B	111.0	H22B—C22—H22C	109.5
C13—C12—H12B	111.0	C12—N1—C15	103.41 (17)
H12A—C12—H12B	109.0	C12—N1—C11	112.27 (16)
C12—C13—C14	104.3 (2)	C15—N1—C11	113.43 (17)
C12—C13—H13A	110.9	C2—O1—H1	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.600 (3)	145
C18—H18···Cg1i	0.93	2.66	3.588 (8)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.600 (3)	145
C18—H18⋯Cg1i	0.93	2.66	3.588 (8)	173

Symmetry code: (i) . Cg1 is the centroid of the C5–C10 benzene ring.