(E)-N-Butyl-3-(3,4-dihy­droxy­phen­yl)acryl­amide hemihydrate

Han, Y.; Hao, M.-H.

doi:10.1107/S1600536812005570

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o727

doi:10.1107/S1600536812005570

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(E)-N-Butyl-3-(3,4-dihydroxyphenyl)acrylamide hemihydrate

Yan Han ^a ^* and Mi-Hua Hao ^a

^aCollege of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang, Henan 453003, People's Republic of China
^*Correspondence e-mail: yanhan1980@126.com

(Received 4 December 2011; accepted 8 February 2012; online 17 February 2012)

In the title compound, C₁₃H₁₇NO₃·0.5H₂O, a new caffeic acid amide derivative, the solvent water molecule lies on a twofold axis and the terminal ethyl group appears disordered with occupancy factors of 0.525 (6) and 0.475 (6). The benzene ring makes an angle of 17.3 (2)° with the C=C—C—O linker. The presence of an ethylenic spacer in the caffeic acid amide molecule allows the formation of a conjugated system, strongly stabilized through π-electron delocalization. The C=C double bond in the linker is trans, similar to those previously reported in caffeic esters. The crystal is stabilized by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. The molecules of the caffeic acid amide form a supermolecular planar structure through O—H⋯O hydrogen bonds between a hydroxy group of one caffeic acid molecule and a carbonyl O atom of another. These planes interact via C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For phenolic acid compounds used in biology and medicine, see: Altuğ et al. (2008 ). For synthetic work on the similar compounds, see: Bylov et al. (1999 ). For compounds with similar properties, see: Son & Lewis (2002 ); Menezes et al. (2001 ); Lee et al. (2005 ). For the structure analysis of a similar compound, see: Xia et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₇NO₃·0.5H₂O
M_r = 244.29
Monoclinic, C 2/c
a = 12.860 (7) Å
b = 14.928 (8) Å
c = 15.015 (11) Å
β = 113.967 (6)°
V = 2634 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.977, T_max = 0.983
7822 measured reflections
2581 independent reflections
1895 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.04
2581 reflections
180 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3ⁱ	0.85	1.91	2.7402 (19)	165
O4—H4B⋯O3ⁱⁱ	0.85	1.91	2.7402 (19)	165
N1—H1B⋯O2ⁱⁱⁱ	0.86	2.29	3.129 (2)	165
N1—H1B⋯O1ⁱⁱⁱ	0.86	2.58	3.143 (3)	124
O1—H1A⋯O3^iv	0.82	1.94	2.7378 (19)	162
O2—H2A⋯O4^v	0.82	2.00	2.8217 (18)	177
C7—H7⋯O3	0.93	2.48	2.837 (2)	103
C8—H8⋯O2ⁱⁱⁱ	0.93	2.55	3.330 (2)	142
Symmetry codes: (i) x, y, z+1; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005570/bg2440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005570/bg2440Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005570/bg2440Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812005570/bg2440Isup4.cml

checkCIF report

Comment top

Phenolic acids and their derivatives (esters, amides) are widely distributed in plants and can be present in considerable amounts in the human diet, which attract much attention in biology and medicine (Altuğ et al., 2008). Phenolic acid amides, is a large class of organic compounds formed by the condensation reaction of aromatic acid and amine (Bylov et al., 1999). The –CO—NH– backbone makes amides have the pharmacological functionality such as anti-proliferative, antiviral, antimalarial, general anesthetics and antimicrobials. Therefore, more and more phenolic acid amides have already been researched purposively and developed as potential anti-proliferative, antiviral, antimalarial, and antimicrobials drugs in recent years (Son & Lewis, 2002; Menezes et al., 2001; Lee et al., 2005). So in this paper, we synthesized and report on the structure of a new caffeic acid amide derivative, (E)-N-butyl-3-(3,4-dihydroxyphenyl)acrylamide monohydrate.

In the title compound (Fig. 1), all values of the geometric parameters are normal, the terminal C12—C13 group being disorderd with occupation factors of 0.525/0.475 (6) for both moieties. The benzene ring is planar within experimental observation (r.m.s. deviation: 0.005Å) and it makes an angle of 17.3 (2)° to the (C7—C8—C9—O3) linker. In the case of caffeic amide, the presence of an ethylenic spacer allows the formation of a conjugated system, strongly stabilized through π-electron delocalization. The C7═C8 bond is a trans-double bond, the same as in caffeic esters reported before (Xia et al., 2008).

The crystal is stabilized by intermolecular O—H···O, N—H···O, O—H···N and C—H···O hydrogen bonds (Fig. 2). The molecules of the caffeic acid amide form a supermolecule plane structure through O—H···O hydrogen bonds between a hydroxyl of a caffeic acid and carbonyl O atom from another caffeic acid molecule. The supermolecule plane interacts with the another plane with C—H···O, O—H···O, N—H···O and O—H···N hydrogen bonds to form a three-dimensional network.

Related literature top

For phenolic acid compounds used in biology and medicine, see: Altuğ et al. (2008). For synthetic work on the similar compounds, see: Bylov et al. (1999). For compounds with similar properties, see: Son & Lewis (2002); Menezes et al. (2001); Lee et al. (2005). For the structure analysis of other caffeic esters, see: Xia et al. (2008). [Please check added text]

Experimental top

To a stirred THF solution (15 ml) of commercial caffeic acid (0.179 g, 1 mmol) was added DCC (1.5 mmol) in THF (5 ml) at 0°C. The reaction mixture was stirred for 2 h at 0°C and n-butylamine (0.088 g, 1.2 mmol) was added for reacting overnight at room temperature, and then the precipitated dicyclohexylurea was filtered and washed with tetrahydrofuran. The combined filtrates were evaporated, the residue was extracted with EtOAc, and the extract was washed with 1 N NaHCO₃, H₂O, and 1 N HCl, dried over Na₂SO₄, and evaporated. The title compound was obtained by elution of the column with 25% petrole:EtOAc and recrystallized to give the pale yellow block crystal.

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of (E)-N-butyl-3-(3,4-dihydroxyphenyl)acrylamide monohydrate with displacement ellipsoids at the 30% probability level. In open bonds, the minor part of the disordered tail.
	Fig. 2. The two-dimensional plane formed by the hydrogen bonds of the molecules (Dashed lines represent hydrogen bonds, some of the H and C atoms have been omitted)

(E)-N-Butyl-3-(3,4-dihydroxyphenyl)acrylamide monohydrate top

Crystal data top

C₁₃H₁₇NO₃·0.5H₂O	F(000) = 1048
M_r = 244.29	D_x = 1.232 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2581 reflections
a = 12.860 (7) Å	θ = 2.2–26.0°
b = 14.928 (8) Å	µ = 0.09 mm⁻¹
c = 15.015 (11) Å	T = 296 K
β = 113.967 (6)°	Block, yellow
V = 2634 (3) Å³	0.28 × 0.22 × 0.19 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −15→15
T_min = 0.977, T_max = 0.983	k = −18→15
7822 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0532P)² + 1.0544P] where P = (F_o² + 2F_c²)/3
2581 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₇NO₃·0.5H₂O	V = 2634 (3) Å³
M_r = 244.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.860 (7) Å	µ = 0.09 mm⁻¹
b = 14.928 (8) Å	T = 296 K
c = 15.015 (11) Å	0.28 × 0.22 × 0.19 mm
β = 113.967 (6)°

Data collection top

Bruker SMART APEX CCD diffractometer	2581 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	1895 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.983	R_int = 0.025
7822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
2581 reflections	Δρ_min = −0.21 e Å⁻³
180 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. The terminal C13 and methylene C12 have been treated disorderd.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O4	0.5000	0.79934 (9)	0.7500	0.0471 (4)
H4A	0.5047	0.7659	0.7973	0.057*	0.50
H4B	0.4953	0.7659	0.7027	0.057*	0.50
N1	0.63571 (12)	0.56741 (9)	−0.01730 (9)	0.0517 (4)
H1B	0.6878	0.5587	0.0401	0.062*
O1	0.83466 (10)	0.95089 (8)	0.33417 (8)	0.0653 (4)
H1A	0.8785	0.9099	0.3375	0.098*
O2	0.67900 (9)	1.07499 (8)	0.30337 (8)	0.0558 (3)
H2A	0.6254	1.1101	0.2869	0.084*
O3	0.51295 (9)	0.66595 (7)	−0.12054 (7)	0.0493 (3)
C1	0.53067 (15)	0.93015 (13)	0.09233 (13)	0.0656 (6)
H1	0.4611	0.9268	0.0388	0.079*
C2	0.55145 (15)	1.00043 (13)	0.15684 (13)	0.0638 (5)
H2	0.4962	1.0443	0.1459	0.077*
C3	0.65313 (13)	1.00632 (11)	0.23735 (11)	0.0491 (4)
C4	0.73642 (13)	0.94036 (11)	0.25296 (11)	0.0479 (4)
C5	0.71557 (13)	0.87094 (11)	0.18753 (11)	0.0498 (4)
H5	0.7713	0.8277	0.1977	0.060*
C6	0.61164 (14)	0.86440 (12)	0.10578 (11)	0.0522 (4)
C7	0.58305 (13)	0.79218 (12)	0.03400 (12)	0.0520 (4)
H7	0.5189	0.8017	−0.0233	0.062*
C8	0.63569 (13)	0.71565 (11)	0.03940 (11)	0.0483 (4)
H8	0.7026	0.7038	0.0935	0.058*
C9	0.59066 (12)	0.64825 (10)	−0.03873 (10)	0.0410 (4)
C10	0.60274 (16)	0.49214 (12)	−0.08466 (13)	0.0608 (5)
H10A	0.5750	0.5145	−0.1509	0.073*
H10B	0.5411	0.4598	−0.0776	0.073*
C11	0.69973 (18)	0.42951 (12)	−0.06711 (14)	0.0678 (5)
H11A	0.7326	0.4095	0.0002	0.081*
H11B	0.7585	0.4582	−0.0819	0.081*
C12	0.6467 (8)	0.3505 (6)	−0.1365 (8)	0.077 (2)	0.525 (6)
H12A	0.5909	0.3206	−0.1188	0.093*	0.525 (6)
H12B	0.6088	0.3720	−0.2029	0.093*	0.525 (6)
C13	0.7411 (5)	0.2857 (3)	−0.1286 (4)	0.097 (2)	0.525 (6)
H13A	0.7933	0.3148	−0.1503	0.146*	0.525 (6)
H13B	0.7089	0.2342	−0.1686	0.146*	0.525 (6)
H13C	0.7808	0.2673	−0.0620	0.146*	0.525 (6)
C12'	0.6881 (7)	0.3529 (8)	−0.1425 (9)	0.073 (2)	0.475 (6)
H12C	0.6553	0.3766	−0.2083	0.088*	0.475 (6)
H12D	0.7624	0.3283	−0.1305	0.088*	0.475 (6)
C13'	0.6133 (5)	0.2818 (4)	−0.1313 (4)	0.098 (2)	0.475 (6)
H13D	0.6453	0.2599	−0.0655	0.147*	0.475 (6)
H13E	0.6074	0.2334	−0.1752	0.147*	0.475 (6)
H13F	0.5391	0.3061	−0.1458	0.147*	0.475 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0635 (10)	0.0324 (8)	0.0410 (8)	0.000	0.0166 (7)	0.000
N1	0.0572 (8)	0.0449 (8)	0.0358 (7)	0.0049 (6)	0.0011 (6)	0.0003 (6)
O1	0.0455 (6)	0.0695 (9)	0.0532 (7)	0.0148 (6)	−0.0085 (5)	−0.0213 (6)
O2	0.0493 (6)	0.0568 (7)	0.0478 (7)	0.0099 (5)	0.0059 (5)	−0.0159 (5)
O3	0.0523 (6)	0.0427 (7)	0.0359 (6)	−0.0050 (5)	0.0005 (5)	0.0034 (5)
C1	0.0442 (9)	0.0799 (14)	0.0484 (10)	0.0186 (9)	−0.0062 (8)	−0.0193 (9)
C2	0.0478 (9)	0.0726 (13)	0.0521 (10)	0.0236 (9)	0.0006 (8)	−0.0175 (9)
C3	0.0446 (8)	0.0536 (10)	0.0400 (8)	0.0058 (7)	0.0079 (7)	−0.0120 (7)
C4	0.0378 (8)	0.0562 (10)	0.0373 (8)	0.0061 (7)	0.0024 (6)	−0.0053 (7)
C5	0.0412 (8)	0.0523 (10)	0.0447 (9)	0.0120 (7)	0.0060 (7)	−0.0071 (7)
C6	0.0457 (9)	0.0580 (11)	0.0399 (9)	0.0090 (7)	0.0042 (7)	−0.0110 (8)
C7	0.0413 (8)	0.0614 (11)	0.0389 (8)	0.0057 (7)	0.0015 (7)	−0.0087 (7)
C8	0.0424 (8)	0.0521 (10)	0.0372 (8)	0.0028 (7)	0.0025 (7)	−0.0036 (7)
C9	0.0393 (7)	0.0435 (9)	0.0344 (8)	−0.0038 (6)	0.0092 (6)	0.0020 (6)
C10	0.0609 (11)	0.0474 (11)	0.0547 (10)	−0.0030 (8)	0.0033 (9)	−0.0042 (8)
C11	0.0828 (14)	0.0510 (11)	0.0556 (11)	0.0111 (10)	0.0138 (10)	0.0000 (9)
C12	0.096 (6)	0.048 (4)	0.090 (4)	−0.003 (4)	0.040 (4)	−0.018 (3)
C13	0.141 (5)	0.061 (3)	0.106 (4)	0.029 (3)	0.067 (3)	−0.009 (2)
C12'	0.076 (5)	0.066 (5)	0.089 (4)	−0.003 (4)	0.044 (4)	−0.008 (3)
C13'	0.113 (5)	0.074 (4)	0.109 (4)	−0.002 (3)	0.046 (4)	0.001 (3)

Geometric parameters (Å, º) top

O4—H4A	0.8501	C8—C9	1.474 (2)
O4—H4B	0.8501	C8—H8	0.9300
N1—C9	1.321 (2)	C10—C11	1.494 (3)
N1—C10	1.455 (2)	C10—H10A	0.9700
N1—H1B	0.8600	C10—H10B	0.9700
O1—C4	1.3624 (19)	C11—C12	1.537 (9)
O1—H1A	0.8200	C11—C12'	1.574 (11)
O2—C3	1.3699 (19)	C11—H11A	0.9700
O2—H2A	0.8200	C11—H11B	0.9700
O3—C9	1.2571 (18)	C12—C13	1.519 (10)
C1—C2	1.378 (2)	C12—H12A	0.9700
C1—C6	1.385 (2)	C12—H12B	0.9700
C1—H1	0.9300	C13—H13A	0.9600
C2—C3	1.377 (2)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.403 (2)	C12'—C13'	1.487 (11)
C4—C5	1.377 (2)	C12'—H12C	0.9700
C5—C6	1.403 (2)	C12'—H12D	0.9700
C5—H5	0.9300	C13'—H13D	0.9600
C6—C7	1.462 (2)	C13'—H13E	0.9600
C7—C8	1.314 (2)	C13'—H13F	0.9600
C7—H7	0.9300

H4A—O4—H4B	108.0	N1—C10—C11	111.97 (15)
C9—N1—C10	124.15 (14)	N1—C10—H10A	109.2
C9—N1—H1B	117.9	C11—C10—H10A	109.2
C10—N1—H1B	117.9	N1—C10—H10B	109.2
C4—O1—H1A	109.5	C11—C10—H10B	109.2
C3—O2—H2A	109.5	H10A—C10—H10B	107.9
C2—C1—C6	121.15 (15)	C10—C11—C12	104.6 (4)
C2—C1—H1	119.4	C10—C11—C12'	120.0 (4)
C6—C1—H1	119.4	C10—C11—H11A	110.8
C3—C2—C1	120.63 (15)	C12—C11—H11A	110.8
C3—C2—H2	119.7	C12'—C11—H11A	113.6
C1—C2—H2	119.7	C10—C11—H11B	110.8
O2—C3—C2	123.23 (14)	C12—C11—H11B	110.8
O2—C3—C4	117.38 (14)	C12'—C11—H11B	90.6
C2—C3—C4	119.37 (15)	H11A—C11—H11B	108.9
O1—C4—C5	124.49 (14)	C13—C12—C11	108.4 (6)
O1—C4—C3	115.86 (14)	C13—C12—H12A	110.0
C5—C4—C3	119.65 (14)	C11—C12—H12A	110.0
C4—C5—C6	121.09 (14)	C13—C12—H12B	110.0
C4—C5—H5	119.5	C11—C12—H12B	110.0
C6—C5—H5	119.5	H12A—C12—H12B	108.4
C1—C6—C5	118.09 (15)	C13'—C12'—C11	108.3 (6)
C1—C6—C7	117.78 (15)	C13'—C12'—H12C	110.0
C5—C6—C7	124.13 (15)	C11—C12'—H12C	110.0
C8—C7—C6	128.82 (15)	C13'—C12'—H12D	110.0
C8—C7—H7	115.6	C11—C12'—H12D	110.0
C6—C7—H7	115.6	H12C—C12'—H12D	108.4
C7—C8—C9	121.24 (15)	C12'—C13'—H13D	109.5
C7—C8—H8	119.4	C12'—C13'—H13E	109.5
C9—C8—H8	119.4	H13D—C13'—H13E	109.5
O3—C9—N1	121.73 (14)	C12'—C13'—H13F	109.5
O3—C9—C8	122.27 (14)	H13D—C13'—H13F	109.5
N1—C9—C8	116.00 (13)	H13E—C13'—H13F	109.5

C6—C1—C2—C3	−0.9 (3)	C5—C6—C7—C8	12.7 (3)
C1—C2—C3—O2	179.32 (18)	C6—C7—C8—C9	176.70 (16)
C1—C2—C3—C4	0.6 (3)	C10—N1—C9—O3	1.0 (2)
O2—C3—C4—O1	1.2 (2)	C10—N1—C9—C8	−179.89 (15)
C2—C3—C4—O1	179.99 (17)	C7—C8—C9—O3	12.8 (2)
O2—C3—C4—C5	−178.59 (15)	C7—C8—C9—N1	−166.28 (16)
C2—C3—C4—C5	0.2 (3)	C9—N1—C10—C11	148.87 (17)
O1—C4—C5—C6	179.54 (17)	N1—C10—C11—C12	174.2 (4)
C3—C4—C5—C6	−0.7 (3)	N1—C10—C11—C12'	−169.8 (4)
C2—C1—C6—C5	0.4 (3)	C10—C11—C12—C13	176.3 (5)
C2—C1—C6—C7	−179.91 (18)	C12'—C11—C12—C13	37.4 (19)
C4—C5—C6—C1	0.4 (3)	C10—C11—C12'—C13'	−74.3 (8)
C4—C5—C6—C7	−179.25 (17)	C12—C11—C12'—C13'	−27.1 (17)
C1—C6—C7—C8	−166.91 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3ⁱ	0.85	1.91	2.7402 (19)	165
O4—H4B···O3ⁱⁱ	0.85	1.91	2.7402 (19)	165
N1—H1B···O2ⁱⁱⁱ	0.86	2.29	3.129 (2)	165
N1—H1B···O1ⁱⁱⁱ	0.86	2.58	3.143 (3)	124
O1—H1A···O3^iv	0.82	1.94	2.7378 (19)	162
O2—H2A···O4^v	0.82	2.00	2.8217 (18)	177
C7—H7···O3	0.93	2.48	2.837 (2)	103
C8—H8···O2ⁱⁱⁱ	0.93	2.55	3.330 (2)	142

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO₃·0.5H₂O
M_r	244.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	12.860 (7), 14.928 (8), 15.015 (11)
β (°)	113.967 (6)
V (Å³)	2634 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7822, 2581, 1895
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.04
No. of reflections	2581
No. of parameters	180
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: SMART (Bruker, 2008), SAINT (Bruker, 2008), 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
O4—H4A···O3ⁱ	0.85	1.91	2.7402 (19)	164.7
O4—H4B···O3ⁱⁱ	0.85	1.91	2.7402 (19)	164.7
N1—H1B···O2ⁱⁱⁱ	0.86	2.29	3.129 (2)	165.0
N1—H1B···O1ⁱⁱⁱ	0.86	2.58	3.143 (3)	123.6
O1—H1A···O3^iv	0.82	1.94	2.7378 (19)	162.4
O2—H2A···O4^v	0.82	2.00	2.8217 (18)	177.2
C7—H7···O3	0.93	2.48	2.837 (2)	102.9
C8—H8···O2ⁱⁱⁱ	0.93	2.55	3.330 (2)	141.9

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

Acknowledgements

This work was supported by Xinxiang University.

References

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