2,6-Di-tert-butyl-4-(morpholinometh­yl)­phenol monohydrate

Zeng, T.; Ren, W.-Z.

doi:10.1107/S1600536807068754

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o406

doi:10.1107/S1600536807068754

Open

access

2,6-Di-tert-butyl-4-(morpholinomethyl)phenol monohydrate

Tao Zeng ^a ^* and Wan-Zhong Ren ^a

^aChemistry and Biology College, Yantai University, Yantai 264005, People's Republic of China
^*Correspondence e-mail: zengtaotj@126.com

(Received 20 November 2007; accepted 29 December 2007; online 9 January 2008)

In the title compound, C₁₉H₃₁NO₂·H₂O, the morpholine ring adopts a chair conformation, while the phenolic hydroxyl group is sterically hindered by the adjacent tert-butyl groups. The crystal structure is stabilized by a number of O—H⋯O, O—H⋯N and C—H⋯O hydrogen-bonding interactions, involving both the organic and the solvent molecules.

Related literature

For related literature, see: Shu et al. (2005 ); Zeng & Chen (2006 ); Zeng et al. (2006 ); Yamazaki & Seguchi (1997 ); Steiner (1996 ); Rieker (1968 ).

Experimental

Crystal data

C₁₉H₃₁NO₂·H₂O
M_r = 323.46
Monoclinic, P 2₁ /n
a = 10.1461 (14) Å
b = 9.7118 (12) Å
c = 19.966 (2) Å
β = 95.166 (8)°
V = 1959.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 (2) K
0.32 × 0.30 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.97, T_max = 0.98
9174 measured reflections
3412 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.151
S = 1.03
3412 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O2ⁱ	0.86 (3)	2.13 (3)	2.884 (2)	146 (3)
O3—H3A⋯N1ⁱⁱ	0.83 (3)	2.10 (3)	2.915 (2)	170 (3)
O1—H1⋯O3	0.85 (3)	1.91 (3)	2.734 (2)	162 (3)
C12—H12B⋯O3	0.96	2.47	3.410 (3)	167
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068754/bg2147sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068754/bg2147Isup2.hkl

checkCIF report

Comment top

Hindered phenol antioxidants are widely used in polymers and lubricants. They can protect polymers by increasing both their process and long-term stability against oxidative degradation (Yamazaki & Seguchi, 1997). In our research, derivates of 2,6-di-tert-butyl-4-(alkylamino)methylphenol have been studied (Shu et al., 2005; Zeng et al., 2006; Zeng & Chen, 2006). In a former paper, we have reported the transformation of 2,6-di-tert-butyl-4-(alkylamino)methyl-phenols to N,N-bis(3,5-di-tert-butyl- 4-hydroxylbenzyl)-N-alkylamines (Zeng et al., 2006), and proposed a mechanism by which 2,6-di-tert-butyl-4-(alkylamino)methyl-phenols could trnsform to 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone and then react with another molecule of 2,6-di-tert-butyl-4-(alkylamino)methyl-phenols to yield the N,N-bis(3,5-di-tert-butyl-4-hydroxylbenzyl)-N-alkylamines. To confirm this mechanism, a number of experiments have been carried out, viz., the reaction of 2,6-di-tert-butyl-4-(alkylamino)methyl-phenol with different amines, and the products were analysed carefully. For example, when 2,6-di-tert-butyl-4-(butylamino)methyl-phenol reacts with morpholine the title compound (I) was obtained, but the same result was obtained when different 2,6-di-tert-butyl-4-(alkylamino)methyl-phenols such as 2,6-di-tert-butyl-4-(propylamino)methylphenol or 2,6-di-tert-butyl-4-(iso-propylamino)methylphenol were used instead. This behaviour proves the mechanism proposed.

In the title compound, C₁₉H₃₃NO₃, the morpholine ring adopts a chair conformation, while the phenolic hydroxyl is hindered by the adjacent tert-butyl groups. The crystal structure is stabilized by a number of O—H···O, O—H···N and C—H···O hydrogen-bonding interactions, where both the organic and the solvato molecules take part (Table 1).

Related literature top

For related literature, see: Shu et al. (2005); Zeng & Chen (2006); Zeng et al. (2006); Yamazaki & Seguchi (1997); Steiner (1996); Rieker (1968).

Experimental top

The 2,6-di-tert-butyl-4-(butylamino)methylphenol was prepared by the indirect reductive amination of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with butlyamine and sodium borhydride, and then separated by silica gel flash column chromatography in 61.5% yield. 2,6-Di-tert-butyl-4-(butylamino)methylphenol (2.91 g, 0.01 mol) and morpholine (1.3 g, 0.015 mol) was dissolved in THF (30 ml) and heated to reflux for 6 h. Then the THF and the extra morpholine was evaporated under reduced pressure.The residue was washed with methanol(10 ml) and the title product (2.89 g) was obtained in 89.5% yield. Suitable crystals were obtained by slow evaporation of a mixture of ethyl acetate and THF.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. Molecular diagram of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of (I) viewed down the unique crystallographic b axis, showing H-bonding interactions in dashed lines.

2,6-Di-tert-butyl-4-(morpholinomethyl)phenol monohydrate top

Crystal data top

C₁₉H₃₁NO₂·H₂O	F(000) = 712
M_r = 323.46	D_x = 1.097 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2606 reflections
a = 10.1461 (14) Å	θ = 2.2–24.6°
b = 9.7118 (12) Å	µ = 0.07 mm⁻¹
c = 19.966 (2) Å	T = 294 K
β = 95.166 (8)°	Block, colourless
V = 1959.4 (4) Å³	0.32 × 0.30 × 0.26 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.97, T_max = 0.98	k = −11→11
9174 measured reflections	l = −23→23

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0769P)² + 0.2168P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3412 reflections	Δρ_max = 0.21 e Å⁻³
224 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.059 (5)

Crystal data top

C₁₉H₃₁NO₂·H₂O	V = 1959.4 (4) Å³
M_r = 323.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1461 (14) Å	µ = 0.07 mm⁻¹
b = 9.7118 (12) Å	T = 294 K
c = 19.966 (2) Å	0.32 × 0.30 × 0.26 mm
β = 95.166 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2098 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.98	R_int = 0.044
9174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.21 e Å⁻³
3412 reflections	Δρ_min = −0.22 e Å⁻³
224 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
O1	0.67458 (16)	0.44480 (17)	0.64823 (7)	0.0583 (5)
H1	0.591 (3)	0.445 (3)	0.6451 (13)	0.087*
O2	0.77839 (18)	0.91614 (16)	0.27118 (7)	0.0722 (5)
N1	0.83158 (15)	0.70489 (15)	0.36930 (8)	0.0416 (4)
C1	0.85010 (18)	0.5892 (2)	0.48162 (10)	0.0439 (5)
C2	0.78398 (19)	0.4645 (2)	0.47924 (9)	0.0434 (5)
H2	0.7801	0.4139	0.4396	0.052*
C3	0.72305 (17)	0.41118 (19)	0.53319 (9)	0.0387 (5)
C4	0.72865 (18)	0.4931 (2)	0.59152 (9)	0.0404 (5)
C5	0.79608 (19)	0.6196 (2)	0.59699 (9)	0.0423 (5)
C6	0.85611 (19)	0.6634 (2)	0.54058 (10)	0.0470 (5)
H6	0.9022	0.7464	0.5429	0.056*
C7	0.8063 (2)	0.7062 (2)	0.66190 (11)	0.0547 (6)
C8	0.6688 (3)	0.7499 (3)	0.67925 (14)	0.0918 (10)
H8A	0.6181	0.6697	0.6883	0.138*
H8B	0.6249	0.7994	0.6420	0.138*
H8C	0.6770	0.8081	0.7183	0.138*
C9	0.8780 (3)	0.6257 (3)	0.72030 (11)	0.0782 (8)
H9A	0.8814	0.6803	0.7605	0.117*
H9B	0.9664	0.6047	0.7100	0.117*
H9C	0.8311	0.5417	0.7270	0.117*
C10	0.8867 (3)	0.8386 (3)	0.65505 (14)	0.0845 (9)
H10A	0.8905	0.8893	0.6964	0.127*
H10B	0.8452	0.8939	0.6193	0.127*
H10C	0.9749	0.8153	0.6451	0.127*
C11	0.6553 (2)	0.2692 (2)	0.52747 (10)	0.0473 (5)
C12	0.5064 (2)	0.2830 (3)	0.52936 (14)	0.0780 (8)
H12A	0.4723	0.3461	0.4950	0.117*
H12B	0.4874	0.3171	0.5726	0.117*
H12C	0.4655	0.1946	0.5216	0.117*
C13	0.7121 (3)	0.1735 (3)	0.58367 (15)	0.0959 (10)
H13A	0.6686	0.0858	0.5794	0.144*
H13B	0.6983	0.2132	0.6265	0.144*
H13C	0.8053	0.1614	0.5804	0.144*
C14	0.6772 (3)	0.1980 (3)	0.46143 (15)	0.0934 (10)
H14A	0.7703	0.1846	0.4586	0.140*
H14B	0.6419	0.2542	0.4245	0.140*
H14C	0.6333	0.1104	0.4595	0.140*
C15	0.9192 (2)	0.6354 (2)	0.42175 (10)	0.0561 (6)
H15A	0.9903	0.6978	0.4371	0.067*
H15B	0.9587	0.5558	0.4021	0.067*
C16	0.8039 (2)	0.8458 (2)	0.38799 (10)	0.0503 (5)
H16A	0.8864	0.8958	0.3967	0.060*
H16B	0.7591	0.8459	0.4289	0.060*
C17	0.7184 (3)	0.9162 (2)	0.33275 (11)	0.0682 (7)
H17A	0.6336	0.8696	0.3264	0.082*
H17B	0.7025	1.0105	0.3459	0.082*
C18	0.8050 (3)	0.7790 (2)	0.25213 (11)	0.0656 (7)
H18A	0.8471	0.7798	0.2104	0.079*
H18B	0.7224	0.7288	0.2444	0.079*
C19	0.8934 (2)	0.7072 (2)	0.30551 (10)	0.0558 (6)
H19A	0.9098	0.6136	0.2914	0.067*
H19B	0.9778	0.7547	0.3118	0.067*
O3	0.41145 (17)	0.4475 (2)	0.66808 (10)	0.0767 (6)
H3A	0.346 (3)	0.403 (3)	0.6527 (16)	0.115*
H3B	0.399 (3)	0.471 (3)	0.7087 (16)	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0548 (9)	0.0818 (11)	0.0398 (8)	−0.0044 (8)	0.0121 (7)	0.0068 (7)
O2	0.1162 (14)	0.0551 (10)	0.0476 (10)	0.0132 (9)	0.0196 (9)	0.0160 (8)
N1	0.0445 (9)	0.0453 (10)	0.0363 (9)	0.0052 (7)	0.0108 (7)	0.0080 (7)
C1	0.0354 (11)	0.0524 (12)	0.0441 (12)	0.0105 (9)	0.0040 (9)	0.0157 (10)
C2	0.0432 (11)	0.0515 (12)	0.0356 (11)	0.0133 (9)	0.0045 (9)	0.0030 (9)
C3	0.0363 (10)	0.0429 (11)	0.0370 (11)	0.0086 (8)	0.0040 (8)	0.0052 (9)
C4	0.0377 (10)	0.0491 (12)	0.0347 (11)	0.0070 (9)	0.0054 (8)	0.0077 (9)
C5	0.0406 (11)	0.0436 (11)	0.0420 (11)	0.0091 (9)	−0.0003 (9)	0.0033 (9)
C6	0.0422 (12)	0.0452 (12)	0.0522 (13)	0.0024 (9)	−0.0030 (9)	0.0102 (10)
C7	0.0603 (14)	0.0503 (13)	0.0521 (13)	0.0063 (10)	−0.0022 (11)	−0.0082 (10)
C8	0.083 (2)	0.092 (2)	0.102 (2)	0.0162 (16)	0.0144 (17)	−0.0440 (18)
C9	0.102 (2)	0.0789 (18)	0.0495 (14)	0.0049 (15)	−0.0180 (14)	−0.0085 (13)
C10	0.103 (2)	0.0620 (16)	0.0854 (19)	−0.0092 (15)	−0.0098 (16)	−0.0134 (14)
C11	0.0504 (13)	0.0439 (12)	0.0481 (12)	0.0047 (9)	0.0067 (10)	−0.0006 (9)
C12	0.0541 (15)	0.0781 (17)	0.102 (2)	−0.0066 (13)	0.0081 (14)	−0.0257 (15)
C13	0.109 (2)	0.0592 (16)	0.113 (2)	−0.0132 (15)	−0.0220 (19)	0.0291 (16)
C14	0.118 (3)	0.0663 (17)	0.103 (2)	−0.0170 (16)	0.0472 (19)	−0.0360 (16)
C15	0.0447 (12)	0.0689 (15)	0.0561 (13)	0.0127 (10)	0.0117 (10)	0.0226 (11)
C16	0.0641 (14)	0.0479 (12)	0.0399 (11)	0.0012 (10)	0.0097 (10)	−0.0008 (10)
C17	0.097 (2)	0.0583 (14)	0.0510 (14)	0.0245 (13)	0.0166 (13)	0.0106 (11)
C18	0.0961 (18)	0.0651 (16)	0.0373 (12)	0.0021 (13)	0.0152 (12)	0.0048 (11)
C19	0.0669 (15)	0.0560 (13)	0.0477 (13)	0.0063 (11)	0.0230 (11)	0.0037 (10)
O3	0.0590 (11)	0.1028 (15)	0.0710 (12)	−0.0152 (9)	0.0209 (9)	−0.0255 (10)

Geometric parameters (Å, º) top

O1—C4	1.384 (2)	C10—H10B	0.9600
O1—H1	0.85 (3)	C10—H10C	0.9600
O2—C18	1.418 (3)	C11—C12	1.520 (3)
O2—C17	1.420 (3)	C11—C14	1.523 (3)
N1—C16	1.452 (2)	C11—C13	1.529 (3)
N1—C19	1.470 (2)	C12—H12A	0.9600
N1—C15	1.475 (2)	C12—H12B	0.9600
C1—C6	1.377 (3)	C12—H12C	0.9600
C1—C2	1.383 (3)	C13—H13A	0.9600
C1—C15	1.508 (3)	C13—H13B	0.9600
C2—C3	1.389 (3)	C13—H13C	0.9600
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.407 (3)	C14—H14B	0.9600
C3—C11	1.540 (3)	C14—H14C	0.9600
C4—C5	1.406 (3)	C15—H15A	0.9700
C5—C6	1.394 (3)	C15—H15B	0.9700
C5—C7	1.541 (3)	C16—C17	1.505 (3)
C6—H6	0.9300	C16—H16A	0.9700
C7—C8	1.527 (3)	C16—H16B	0.9700
C7—C9	1.532 (3)	C17—H17A	0.9700
C7—C10	1.535 (3)	C17—H17B	0.9700
C8—H8A	0.9600	C18—C19	1.501 (3)
C8—H8B	0.9600	C18—H18A	0.9700
C8—H8C	0.9600	C18—H18B	0.9700
C9—H9A	0.9600	C19—H19A	0.9700
C9—H9B	0.9600	C19—H19B	0.9700
C9—H9C	0.9600	O3—H3A	0.83 (3)
C10—H10A	0.9600	O3—H3B	0.86 (3)

C4—O1—H1	114.2 (18)	C14—C11—C3	111.80 (18)
C18—O2—C17	109.84 (16)	C13—C11—C3	110.69 (17)
C16—N1—C19	108.42 (15)	C11—C12—H12A	109.5
C16—N1—C15	111.52 (16)	C11—C12—H12B	109.5
C19—N1—C15	110.19 (15)	H12A—C12—H12B	109.5
C6—C1—C2	118.17 (18)	C11—C12—H12C	109.5
C6—C1—C15	122.24 (19)	H12A—C12—H12C	109.5
C2—C1—C15	119.50 (19)	H12B—C12—H12C	109.5
C1—C2—C3	123.23 (18)	C11—C13—H13A	109.5
C1—C2—H2	118.4	C11—C13—H13B	109.5
C3—C2—H2	118.4	H13A—C13—H13B	109.5
C2—C3—C4	116.30 (18)	C11—C13—H13C	109.5
C2—C3—C11	120.20 (17)	H13A—C13—H13C	109.5
C4—C3—C11	123.50 (17)	H13B—C13—H13C	109.5
O1—C4—C5	117.30 (17)	C11—C14—H14A	109.5
O1—C4—C3	119.73 (17)	C11—C14—H14B	109.5
C5—C4—C3	122.79 (17)	H14A—C14—H14B	109.5
C6—C5—C4	116.67 (18)	C11—C14—H14C	109.5
C6—C5—C7	120.78 (18)	H14A—C14—H14C	109.5
C4—C5—C7	122.54 (18)	H14B—C14—H14C	109.5
C1—C6—C5	122.79 (19)	N1—C15—C1	113.94 (16)
C1—C6—H6	118.6	N1—C15—H15A	108.8
C5—C6—H6	118.6	C1—C15—H15A	108.8
C8—C7—C9	110.5 (2)	N1—C15—H15B	108.8
C8—C7—C10	106.9 (2)	C1—C15—H15B	108.8
C9—C7—C10	106.0 (2)	H15A—C15—H15B	107.7
C8—C7—C5	110.41 (18)	N1—C16—C17	110.61 (17)
C9—C7—C5	110.66 (17)	N1—C16—H16A	109.5
C10—C7—C5	112.2 (2)	C17—C16—H16A	109.5
C7—C8—H8A	109.5	N1—C16—H16B	109.5
C7—C8—H8B	109.5	C17—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	108.1
C7—C8—H8C	109.5	O2—C17—C16	111.77 (19)
H8A—C8—H8C	109.5	O2—C17—H17A	109.3
H8B—C8—H8C	109.5	C16—C17—H17A	109.3
C7—C9—H9A	109.5	O2—C17—H17B	109.3
C7—C9—H9B	109.5	C16—C17—H17B	109.3
H9A—C9—H9B	109.5	H17A—C17—H17B	107.9
C7—C9—H9C	109.5	O2—C18—C19	111.22 (19)
H9A—C9—H9C	109.5	O2—C18—H18A	109.4
H9B—C9—H9C	109.5	C19—C18—H18A	109.4
C7—C10—H10A	109.5	O2—C18—H18B	109.4
C7—C10—H10B	109.5	C19—C18—H18B	109.4
H10A—C10—H10B	109.5	H18A—C18—H18B	108.0
C7—C10—H10C	109.5	N1—C19—C18	110.34 (18)
H10A—C10—H10C	109.5	N1—C19—H19A	109.6
H10B—C10—H10C	109.5	C18—C19—H19A	109.6
C12—C11—C14	106.5 (2)	N1—C19—H19B	109.6
C12—C11—C13	110.2 (2)	C18—C19—H19B	109.6
C14—C11—C13	106.5 (2)	H19A—C19—H19B	108.1
C12—C11—C3	110.90 (17)	H3A—O3—H3B	108 (3)

C6—C1—C2—C3	0.3 (3)	C6—C5—C7—C10	0.1 (3)
C15—C1—C2—C3	176.91 (17)	C4—C5—C7—C10	179.16 (19)
C1—C2—C3—C4	1.6 (3)	C2—C3—C11—C12	−113.3 (2)
C1—C2—C3—C11	−177.92 (17)	C4—C3—C11—C12	67.3 (2)
C2—C3—C4—O1	−177.58 (16)	C2—C3—C11—C14	5.5 (3)
C11—C3—C4—O1	1.9 (3)	C4—C3—C11—C14	−174.0 (2)
C2—C3—C4—C5	−2.5 (3)	C2—C3—C11—C13	124.1 (2)
C11—C3—C4—C5	177.00 (17)	C4—C3—C11—C13	−55.4 (3)
O1—C4—C5—C6	176.67 (16)	C16—N1—C15—C1	77.3 (2)
C3—C4—C5—C6	1.4 (3)	C19—N1—C15—C1	−162.21 (18)
O1—C4—C5—C7	−2.4 (3)	C6—C1—C15—N1	−99.6 (2)
C3—C4—C5—C7	−177.63 (17)	C2—C1—C15—N1	84.0 (2)
C2—C1—C6—C5	−1.5 (3)	C19—N1—C16—C17	56.5 (2)
C15—C1—C6—C5	−177.96 (17)	C15—N1—C16—C17	177.96 (17)
C4—C5—C6—C1	0.6 (3)	C18—O2—C17—C16	57.6 (3)
C7—C5—C6—C1	179.70 (17)	N1—C16—C17—O2	−57.9 (3)
C6—C5—C7—C8	119.3 (2)	C17—O2—C18—C19	−58.2 (3)
C4—C5—C7—C8	−61.6 (3)	C16—N1—C19—C18	−57.2 (2)
C6—C5—C7—C9	−118.0 (2)	C15—N1—C19—C18	−179.50 (18)
C4—C5—C7—C9	61.0 (3)	O2—C18—C19—N1	59.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2ⁱ	0.86 (3)	2.13 (3)	2.884 (2)	146 (3)
O3—H3A···N1ⁱⁱ	0.83 (3)	2.10 (3)	2.915 (2)	170 (3)
O1—H1···O3	0.85 (3)	1.91 (3)	2.734 (2)	162 (3)
C12—H12B···O3	0.96	2.47	3.410 (3)	167

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₃₁NO₂·H₂O
M_r	323.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	10.1461 (14), 9.7118 (12), 19.966 (2)
β (°)	95.166 (8)
V (Å³)	1959.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.32 × 0.30 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.97, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	9174, 3412, 2098
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.04
No. of reflections	3412
No. of parameters	224
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2ⁱ	0.86 (3)	2.13 (3)	2.884 (2)	146 (3)
O3—H3A···N1ⁱⁱ	0.83 (3)	2.10 (3)	2.915 (2)	170 (3)
O1—H1···O3	0.85 (3)	1.91 (3)	2.734 (2)	162 (3)
C12—H12B···O3	0.96	2.47	3.410 (3)	166.6

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The authors gratefully acknowledge financial support from the Start Foundation for Doctors (HY07116) of Yantai University.

References

Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rieker, A. (1968). Tetrahedron, 24, 103–115. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Shu, X.-G., Zeng, T., Chen, L.-G., Yan, F.-Y. & Zhang, Y.-C. (2005). Acta Cryst. E61, o4192–o4194. Web of Science CSD CrossRef IUCr Journals Google Scholar
Steiner, Th. (1996). Crystallogr. Rev. 6, 1–57. CrossRef CAS Google Scholar
Yamazaki, T. & Seguchi, T. (1997). J. Polym. Sci. Part A Polym. Chem. 35, 2431–2439. CrossRef CAS Google Scholar
Zeng, T. & Chen, L.-G. (2006). Acta Cryst. E62, o2916–o2917. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zeng, T., Chen, L.-G., Li, J.-S., Zhang, Y.-C. & Deng, Y. (2006). J. Chem. Res. (M), pp. 794–796. CrossRef Google Scholar