1-[(2-Hy­droxy­phen­yl)(pyrrolidin-1-yl)­meth­yl]naphthalen-2-ol N,N-dimethyl­formamide monosolvate

Wang, W.

doi:10.1107/S1600536812007787

organic compounds

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Volume 68| Part 3| March 2012| Page o884

doi:10.1107/S1600536812007787

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1-[(2-Hydroxyphenyl)(pyrrolidin-1-yl)methyl]naphthalen-2-ol N,N-dimethylformamide monosolvate

Wen-xiang Wang ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: wxwang@seu.edu.cn

(Received 13 February 2012; accepted 21 February 2012; online 29 February 2012)

The title compound, C₂₁H₂₁NO₂·C₃H₇NO, was synthesized by solvent-free one-pot three-component reaction of naphthalen-2-ol, 2-hydroxybenzaldehyde and pyrrolidine. The dihedral angle between the naphthalene ring system and the benzene ring is 77.74 (6)°. The pyrrolidine ring assumes an envelope conformation. An intramolecular O—H⋯N and an intermolecular O—H⋯O hydrogen bond are observed.

Related literature

For background to Betti-type reactions, see: Pu & Yu (2001 ); Yuan (2005 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₂₁NO₂·C₃H₇NO
M_r = 392.48
Monoclinic, P 2₁ /n
a = 13.675 (3) Å
b = 9.6518 (19) Å
c = 16.505 (3) Å
β = 102.84 (3)°
V = 2123.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.20 mm

Data collection

Rigaku Mercury2 (2 × 2 bin mode) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.963, T_max = 0.989
21445 measured reflections
4874 independent reflections
2223 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.184
S = 1.03
4874 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.82	1.88	2.565 (3)	140
O3—H3A⋯O1	0.82	1.86	2.678 (3)	173

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007787/rz2712sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007787/rz2712Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007787/rz2712Isup3.cml

checkCIF report

Comment top

The so-called Betti base derivatives, which can be synthesized by many ways (Pu & Yu, 2001; Yuan, 2005), have been of great interest in coordination chemistry. Herein the crystal structure of one such compounds obtained by solvent free, one-pot, three-component domino reaction of naphthalen-2-ol, 2-hydroxybenzaldehyde and pyrrolidine is reported.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are well within the expected range. The dihedral angle between the naphthalene ring system and the benzene ring is 77.74 (6)°. The pyrrolidine ring adopts an envelope conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.408 (3) Å and ϕ = 170.7 (5)°. An intramolecular O—H···N hydrogen bond (Table 1) stabilizes the molecular conformation. In the crystal structure, the molecules interact via an intermolecular O—H···O hydrogen bond (Table 1).

Related literature top

For background to Betti-type reactions, see: Pu & Yu (2001); Yuan (2005). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A dry 50 ml flask was charged with 2-hydroxybenzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and pyrrolidine (10 mmol). The mixture was stirred at 100°C for 5 h, then ethanol (15 ml) was added. After refluxing for 30 minutes, the precipitate was filtrated out, washed with ethanol for 3 times and purified by recrystallization from a mixed solution of dichloromethane, methanol and DMF (30:8:10 v/v/v) to give crystals of the title compound suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Intra- and intermolecular hydrogen bonds are shown as dashed lines.

1-[(2-Hydroxyphenyl)(pyrrolidin-1-yl)methyl]naphthalen-2-ol N,N-dimethylformamide monosolvate top

Crystal data top

C₂₁H₂₁NO₂·C₃H₇NO	F(000) = 840
M_r = 392.48	D_x = 1.227 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3860 reflections
a = 13.675 (3) Å	θ = 2.3–27.5°
b = 9.6518 (19) Å	µ = 0.08 mm⁻¹
c = 16.505 (3) Å	T = 293 K
β = 102.84 (3)°	Prism, colourless
V = 2123.9 (7) Å³	0.25 × 0.22 × 0.20 mm
Z = 4

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	4874 independent reflections
Radiation source: fine-focus sealed tube	2223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD Profile fitting scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.963, T_max = 0.989	l = −21→21
21445 measured reflections

Refinement top

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0731P)² + 0.0577P] where P = (F_o² + 2F_c²)/3
4874 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₂₁NO₂·C₃H₇NO	V = 2123.9 (7) Å³
M_r = 392.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.675 (3) Å	µ = 0.08 mm⁻¹
b = 9.6518 (19) Å	T = 293 K
c = 16.505 (3) Å	0.25 × 0.22 × 0.20 mm
β = 102.84 (3)°

Data collection top

Rigaku Mercury2 (2x2 bin mode) diffractometer	4874 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2223 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.989	R_int = 0.100
21445 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
4874 reflections	Δρ_min = −0.17 e Å⁻³
262 parameters

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
O2	0.86622 (14)	0.7318 (2)	1.01567 (12)	0.0696 (6)
H2A	0.8484	0.7762	1.0522	0.104*
O3	0.59379 (14)	1.15741 (19)	1.04615 (12)	0.0620 (6)
H3A	0.5723	1.2281	1.0636	0.093*
N1	0.73008 (15)	0.8368 (2)	1.08164 (11)	0.0421 (5)
C8	0.72196 (18)	0.8476 (3)	0.93131 (15)	0.0396 (6)
C16	0.66100 (19)	0.8697 (2)	0.84998 (15)	0.0414 (6)
C15	0.5776 (2)	0.9595 (3)	0.83292 (16)	0.0508 (7)
H15A	0.5614	1.0099	0.8761	0.061*
C1	0.69749 (19)	0.9227 (2)	1.00552 (14)	0.0397 (6)
H1A	0.6245	0.9335	0.9952	0.048*
C9	0.8026 (2)	0.7581 (3)	0.94091 (17)	0.0508 (7)
C17	0.6846 (2)	0.7971 (3)	0.78094 (16)	0.0518 (7)
C7	0.8420 (2)	1.0914 (3)	1.00816 (15)	0.0540 (7)
H7A	0.8790	1.0181	0.9940	0.065*
C2	0.7445 (2)	1.0671 (3)	1.01694 (14)	0.0422 (6)
C3	0.6901 (2)	1.1791 (3)	1.03819 (15)	0.0485 (7)
C10	0.8248 (2)	0.6866 (3)	0.8726 (2)	0.0648 (9)
H10A	0.8794	0.6267	0.8806	0.078*
C14	0.5201 (2)	0.9739 (3)	0.75428 (19)	0.0639 (8)
H14A	0.4650	1.0330	0.7451	0.077*
C5	0.8301 (3)	1.3300 (3)	1.04007 (18)	0.0706 (10)
H5A	0.8585	1.4179	1.0477	0.085*
C12	0.6236 (3)	0.8158 (4)	0.70070 (17)	0.0679 (9)
H12A	0.6392	0.7685	0.6561	0.082*
C13	0.5429 (3)	0.9011 (4)	0.68713 (19)	0.0734 (10)
H13A	0.5030	0.9113	0.6340	0.088*
C18	0.6664 (2)	0.7135 (3)	1.08117 (17)	0.0628 (9)
H18A	0.6778	0.6458	1.0409	0.075*
H18B	0.5958	0.7382	1.0690	0.075*
C11	0.7670 (2)	0.7048 (3)	0.7955 (2)	0.0651 (9)
H11A	0.7817	0.6557	0.7512	0.078*
C21	0.7284 (2)	0.9051 (3)	1.16070 (15)	0.0596 (8)
H21A	0.6674	0.9587	1.1564	0.072*
H21B	0.7858	0.9658	1.1778	0.072*
C4	0.7332 (3)	1.3106 (3)	1.04918 (17)	0.0636 (9)
H4A	0.6967	1.3851	1.0626	0.076*
C20	0.7325 (3)	0.7847 (3)	1.22155 (18)	0.0734 (10)
H20A	0.8000	0.7729	1.2547	0.088*
H20B	0.6876	0.8013	1.2585	0.088*
C19	0.7004 (3)	0.6593 (4)	1.16925 (18)	0.0850 (11)
H19A	0.6458	0.6123	1.1867	0.102*
H19B	0.7558	0.5951	1.1732	0.102*
C6	0.8852 (2)	1.2218 (4)	1.01990 (18)	0.0667 (9)
H6A	0.9507	1.2357	1.0142	0.080*
N2	0.45935 (18)	1.5046 (3)	1.20142 (17)	0.0669 (7)
O1	0.50827 (19)	1.3762 (2)	1.10246 (16)	0.0883 (8)
C22	0.5038 (2)	1.3964 (4)	1.1737 (3)	0.0729 (9)
H22A	0.5340	1.3312	1.2128	0.087*
C23	0.4627 (3)	1.5224 (4)	1.2890 (2)	0.1042 (13)
H23A	0.5010	1.4487	1.3198	0.156*
H23C	0.3957	1.5206	1.2979	0.156*
H23D	0.4934	1.6096	1.3073	0.156*
C24	0.4053 (3)	1.6046 (4)	1.1449 (3)	0.1163 (15)
H24C	0.4091	1.5807	1.0892	0.174*
H24D	0.4342	1.6946	1.1585	0.174*
H24A	0.3364	1.6056	1.1491	0.174*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0655 (13)	0.0786 (15)	0.0595 (14)	0.0240 (11)	0.0028 (11)	−0.0003 (11)
O3	0.0592 (13)	0.0468 (12)	0.0864 (15)	−0.0006 (10)	0.0300 (11)	−0.0142 (10)
N1	0.0557 (13)	0.0384 (12)	0.0315 (11)	−0.0083 (11)	0.0085 (10)	0.0001 (9)
C8	0.0430 (15)	0.0391 (15)	0.0381 (15)	−0.0027 (12)	0.0116 (12)	−0.0032 (11)
C16	0.0480 (16)	0.0391 (15)	0.0385 (15)	−0.0134 (13)	0.0125 (12)	−0.0023 (11)
C15	0.0569 (18)	0.0499 (18)	0.0439 (16)	−0.0025 (14)	0.0077 (14)	0.0028 (13)
C1	0.0474 (15)	0.0372 (15)	0.0346 (14)	−0.0019 (12)	0.0090 (11)	−0.0002 (11)
C9	0.0529 (17)	0.0527 (18)	0.0465 (17)	0.0006 (15)	0.0105 (14)	−0.0028 (14)
C17	0.0662 (19)	0.0539 (18)	0.0368 (16)	−0.0154 (15)	0.0146 (14)	−0.0106 (13)
C7	0.0608 (19)	0.0584 (19)	0.0433 (16)	−0.0102 (15)	0.0130 (14)	0.0009 (14)
C2	0.0505 (16)	0.0446 (17)	0.0309 (14)	−0.0086 (13)	0.0079 (12)	0.0009 (11)
C3	0.0684 (19)	0.0371 (16)	0.0394 (15)	−0.0053 (14)	0.0108 (14)	−0.0048 (12)
C10	0.064 (2)	0.067 (2)	0.069 (2)	0.0125 (16)	0.0265 (18)	−0.0124 (17)
C14	0.0599 (19)	0.069 (2)	0.056 (2)	−0.0037 (16)	−0.0010 (16)	0.0133 (16)
C5	0.102 (3)	0.054 (2)	0.0509 (19)	−0.035 (2)	0.0074 (19)	−0.0035 (15)
C12	0.093 (3)	0.075 (2)	0.0352 (18)	−0.031 (2)	0.0135 (17)	−0.0097 (15)
C13	0.087 (3)	0.084 (3)	0.0406 (19)	−0.026 (2)	−0.0045 (17)	0.0112 (17)
C18	0.084 (2)	0.0501 (18)	0.0505 (18)	−0.0236 (16)	0.0062 (15)	0.0073 (14)
C11	0.075 (2)	0.066 (2)	0.064 (2)	−0.0113 (18)	0.0362 (18)	−0.0245 (16)
C21	0.085 (2)	0.0585 (19)	0.0348 (15)	−0.0073 (17)	0.0131 (15)	−0.0049 (14)
C4	0.093 (3)	0.0411 (18)	0.0552 (19)	−0.0131 (17)	0.0138 (17)	−0.0047 (14)
C20	0.094 (2)	0.080 (2)	0.0452 (18)	−0.0161 (19)	0.0134 (17)	0.0097 (17)
C19	0.114 (3)	0.077 (2)	0.058 (2)	−0.030 (2)	0.006 (2)	0.0151 (19)
C6	0.071 (2)	0.077 (2)	0.0511 (19)	−0.030 (2)	0.0121 (16)	0.0032 (17)
N2	0.0663 (17)	0.0551 (17)	0.082 (2)	0.0039 (14)	0.0228 (15)	−0.0131 (15)
O1	0.1021 (19)	0.0734 (17)	0.101 (2)	−0.0031 (13)	0.0463 (16)	−0.0201 (15)
C22	0.065 (2)	0.056 (2)	0.097 (3)	−0.0124 (17)	0.018 (2)	−0.010 (2)
C23	0.136 (4)	0.094 (3)	0.084 (3)	−0.007 (3)	0.028 (2)	−0.020 (2)
C24	0.130 (4)	0.099 (3)	0.119 (3)	0.048 (3)	0.027 (3)	0.023 (3)

Geometric parameters (Å, º) top

O2—C9	1.366 (3)	C5—H5A	0.9300
O2—H2A	0.8200	C12—C13	1.356 (4)
O3—C3	1.368 (3)	C12—H12A	0.9300
O3—H3A	0.8200	C13—H13A	0.9300
N1—C21	1.467 (3)	C18—C19	1.518 (4)
N1—C18	1.473 (3)	C18—H18A	0.9700
N1—C1	1.489 (3)	C18—H18B	0.9700
C8—C9	1.382 (3)	C11—H11A	0.9300
C8—C16	1.430 (3)	C21—C20	1.529 (4)
C8—C1	1.523 (3)	C21—H21A	0.9700
C16—C15	1.410 (4)	C21—H21B	0.9700
C16—C17	1.434 (3)	C4—H4A	0.9300
C15—C14	1.367 (4)	C20—C19	1.495 (4)
C15—H15A	0.9300	C20—H20A	0.9700
C1—C2	1.529 (3)	C20—H20B	0.9700
C1—H1A	0.9800	C19—H19A	0.9700
C9—C10	1.411 (4)	C19—H19B	0.9700
C17—C12	1.411 (4)	C6—H6A	0.9300
C17—C11	1.415 (4)	N2—C22	1.339 (4)
C7—C6	1.386 (4)	N2—C24	1.428 (4)
C7—C2	1.393 (4)	N2—C23	1.446 (4)
C7—H7A	0.9300	O1—C22	1.207 (4)
C2—C3	1.400 (4)	C22—H22A	0.9300
C3—C4	1.394 (4)	C23—H23A	0.9600
C10—C11	1.351 (4)	C23—H23C	0.9600
C10—H10A	0.9300	C23—H23D	0.9600
C14—C13	1.404 (4)	C24—H24C	0.9600
C14—H14A	0.9300	C24—H24D	0.9600
C5—C6	1.372 (4)	C24—H24A	0.9600
C5—C4	1.379 (4)

C9—O2—H2A	109.5	N1—C18—H18A	111.2
C3—O3—H3A	109.5	C19—C18—H18A	111.2
C21—N1—C18	104.0 (2)	N1—C18—H18B	111.2
C21—N1—C1	116.0 (2)	C19—C18—H18B	111.2
C18—N1—C1	112.29 (19)	H18A—C18—H18B	109.2
C9—C8—C16	119.0 (2)	C10—C11—C17	121.3 (3)
C9—C8—C1	121.2 (2)	C10—C11—H11A	119.4
C16—C8—C1	119.8 (2)	C17—C11—H11A	119.4
C15—C16—C8	123.8 (2)	N1—C21—C20	103.7 (2)
C15—C16—C17	117.1 (2)	N1—C21—H21A	111.0
C8—C16—C17	119.1 (2)	C20—C21—H21A	111.0
C14—C15—C16	121.4 (3)	N1—C21—H21B	111.0
C14—C15—H15A	119.3	C20—C21—H21B	111.0
C16—C15—H15A	119.3	H21A—C21—H21B	109.0
N1—C1—C8	109.61 (19)	C5—C4—C3	119.9 (3)
N1—C1—C2	111.41 (19)	C5—C4—H4A	120.0
C8—C1—C2	111.8 (2)	C3—C4—H4A	120.0
N1—C1—H1A	107.9	C19—C20—C21	105.9 (2)
C8—C1—H1A	107.9	C19—C20—H20A	110.6
C2—C1—H1A	107.9	C21—C20—H20A	110.6
O2—C9—C8	123.5 (2)	C19—C20—H20B	110.6
O2—C9—C10	115.1 (3)	C21—C20—H20B	110.6
C8—C9—C10	121.5 (3)	H20A—C20—H20B	108.7
C12—C17—C11	121.5 (3)	C20—C19—C18	105.2 (3)
C12—C17—C16	119.6 (3)	C20—C19—H19A	110.7
C11—C17—C16	118.9 (3)	C18—C19—H19A	110.7
C6—C7—C2	121.8 (3)	C20—C19—H19B	110.7
C6—C7—H7A	119.1	C18—C19—H19B	110.7
C2—C7—H7A	119.1	H19A—C19—H19B	108.8
C7—C2—C3	118.1 (2)	C5—C6—C7	119.0 (3)
C7—C2—C1	121.7 (2)	C5—C6—H6A	120.5
C3—C2—C1	120.2 (2)	C7—C6—H6A	120.5
O3—C3—C4	121.0 (3)	C22—N2—C24	120.8 (3)
O3—C3—C2	118.8 (2)	C22—N2—C23	121.2 (3)
C4—C3—C2	120.1 (3)	C24—N2—C23	118.0 (3)
C11—C10—C9	120.3 (3)	O1—C22—N2	125.8 (4)
C11—C10—H10A	119.9	O1—C22—H22A	117.1
C9—C10—H10A	119.9	N2—C22—H22A	117.1
C15—C14—C13	121.1 (3)	N2—C23—H23A	109.5
C15—C14—H14A	119.4	N2—C23—H23C	109.5
C13—C14—H14A	119.4	H23A—C23—H23C	109.5
C6—C5—C4	121.1 (3)	N2—C23—H23D	109.5
C6—C5—H5A	119.5	H23A—C23—H23D	109.5
C4—C5—H5A	119.5	H23C—C23—H23D	109.5
C13—C12—C17	121.5 (3)	N2—C24—H24C	109.5
C13—C12—H12A	119.3	N2—C24—H24D	109.5
C17—C12—H12A	119.3	H24C—C24—H24D	109.5
C12—C13—C14	119.3 (3)	N2—C24—H24A	109.5
C12—C13—H13A	120.4	H24C—C24—H24A	109.5
C14—C13—H13A	120.4	H24D—C24—H24A	109.5
N1—C18—C19	102.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	1.88	2.565 (3)	140
O3—H3A···O1	0.82	1.86	2.678 (3)	173

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NO₂·C₃H₇NO
M_r	392.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.675 (3), 9.6518 (19), 16.505 (3)
β (°)	102.84 (3)
V (Å³)	2123.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.963, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	21445, 4874, 2223
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.184, 1.03
No. of reflections	4874
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	1.88	2.565 (3)	140.0
O3—H3A···O1	0.82	1.86	2.678 (3)	172.6

Acknowledgements

This work was supported by Southeast University.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Pu, L. & Yu, H. B. (2001). Chem. Rev. 101, 757–824. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yuan, C.-L. (2005). Acta Cryst. E61, o1182–o1183. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o884

doi:10.1107/S1600536812007787

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

1-[(2-Hy­dr­oxy­phen­yl)(pyrrolidin-1-yl)­meth­yl]naphthalen-2-ol N,N-di­methyl­formamide monosolvate

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Acknowledgements

References

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1-[(2-Hydroxyphenyl)(pyrrolidin-1-yl)methyl]naphthalen-2-ol N,N-dimethylformamide monosolvate