(S,Z)-3-Phenyl-2-[(1,1,1-tri-chloro-7-meth-oxy-2,7-dioxohept-3-en-4-yl)amino]-propanoic acid monohydrate.

In the title compound, C17H18Cl3NO5·H2O, intra-molecular N-H⋯O and C-H⋯Cl hydrogen bonds form S(6) and S(5) ring motifs, respectively. The chiral organic mol-ecule is connected to the solvent water mol-ecule by a short O-H⋯O hydrogen bond. In the crystal, a weak C-H⋯Cl inter-action connects the organic mol-ecules along [100] while the water mol-ecules act as bridges between the organic mol-ecules in both the [100] and [010] directions, generating layers parallel to the ab plane.

Related literature

For the synthesis of the title compound and a similar crystal structure, see: Flores et al. (2008 ▶). For information about levulinic acid and the biological properties of its derivatives, see: Flores et al. (2013 ▶); Hachuła et al. (2013 ▶); Lo & Ng (2008 ▶). For short inter­molecular hydrogen-bond inter­actions, see: Pojarová et al. (2010 ▶). For intra­molecular hydrogen-bonding systems, see: da Costa et al. (2013 ▶).

Experimental

Crystal data

C17H18Cl3NO5·H2O

M = 440.69

Triclinic,

a = 5.6684 (16) Å

b = 8.601 (3) Å

c = 10.336 (3) Å

α = 87.720 (19)°

β = 85.696 (17)°

γ = 85.649 (17)°

V = 500.8 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.98 × 0.30 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: Gaussian (XPREP; Bruker, 2006 ▶) T min = 0.881, T max = 1

13424 measured reflections

6020 independent reflections

4784 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.04

6020 reflections

256 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack parameter determined using 1984 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.04 (2)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814000154/pk2509sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000154/pk2509Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000154/pk2509Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H18Cl3NO5·H2O	F(000) = 228
Mr = 440.69	Dx = 1.461 Mg m−3
Triclinic, P1	Melting point: 393 K
a = 5.6684 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.601 (3) Å	Cell parameters from 3866 reflections
c = 10.336 (3) Å	θ = 3.0–25.5°
α = 87.720 (19)°	µ = 0.49 mm−1
β = 85.696 (17)°	T = 296 K
γ = 85.649 (17)°	Blade, colorless
V = 500.8 (2) Å3	0.98 × 0.30 × 0.12 mm
Z = 1

Bruker APEXII CCD diffractometer	6020 independent reflections
Radiation source: fine-focus sealed tube	4784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.7°, θmin = 2.4°
Absorption correction: gaussian (XPREP; Bruker, 2006)	h = −8→8
Tmin = 0.881, Tmax = 1	k = −12→12
13424 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.0376P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.41 e Å−3
6020 reflections	Δρmin = −0.32 e Å−3
256 parameters	Absolute structure: Flack parameter determined using 1984 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.04 (2)

Experimental. Absorption correction: XPREP (Bruker, 2006) was used to perform the Gaussian absorption correction based on the face-indexed crystal size.

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.

	x	y	z	Uiso*/Ueq
O33	0.4813 (5)	1.0147 (3)	0.9230 (3)	0.0554 (6)
H33B	0.629 (11)	0.977 (6)	0.919 (5)	0.083*
H41	0.147 (9)	0.465 (6)	0.794 (5)	0.083*
H33A	0.458 (10)	1.092 (7)	0.887 (5)	0.083*
H92	0.352 (9)	0.869 (6)	0.864 (5)	0.083*
Cl1	0.75049 (16)	0.24572 (10)	0.42096 (9)	0.0652 (3)
Cl2	0.50084 (18)	0.01516 (11)	0.57338 (11)	0.0759 (3)
Cl3	0.88358 (15)	0.16349 (14)	0.67617 (11)	0.0742 (3)
N41	0.1053 (4)	0.5403 (3)	0.7462 (2)	0.0403 (5)
C1	0.6395 (5)	0.1924 (3)	0.5785 (3)	0.0432 (6)
C7	−0.1436 (5)	0.7761 (4)	0.3642 (3)	0.0424 (6)
C9	0.0625 (5)	0.7901 (3)	0.8625 (3)	0.0439 (6)
C3	0.3699 (5)	0.4434 (3)	0.5739 (3)	0.0412 (6)
H3	0.4282	0.4569	0.4880	0.049*
C10	−0.0576 (5)	0.6530 (3)	0.8145 (3)	0.0402 (6)
H10	−0.1704	0.6956	0.7526	0.048*
C5	0.1234 (5)	0.6912 (3)	0.5398 (3)	0.0414 (6)
H5A	0.2526	0.7135	0.4764	0.050*
H5B	0.0854	0.7828	0.5913	0.050*
C111	−0.0514 (5)	0.4758 (4)	1.0193 (3)	0.0455 (6)
C2	0.4540 (5)	0.3128 (3)	0.6460 (3)	0.0386 (5)
C6	−0.0917 (6)	0.6567 (4)	0.4700 (3)	0.0472 (7)
H6A	−0.0645	0.5545	0.4328	0.057*
H6B	−0.2285	0.6543	0.5321	0.057*
C11	−0.2023 (5)	0.5712 (4)	0.9264 (3)	0.0475 (7)
H11A	−0.3005	0.6496	0.9745	0.057*
H11B	−0.3071	0.5033	0.8897	0.057*
C112	0.0981 (7)	0.5453 (4)	1.0959 (3)	0.0584 (8)
H112	0.1040	0.6532	1.0916	0.070*
C8	−0.4279 (7)	0.8699 (5)	0.2188 (4)	0.0649 (10)
H8A	−0.5833	0.8501	0.1953	0.097*
H8B	−0.3165	0.8573	0.1446	0.097*
H8C	−0.4299	0.9745	0.2481	0.097*
C116	−0.0616 (8)	0.3156 (4)	1.0306 (4)	0.0638 (9)
H116	−0.1627	0.2664	0.9813	0.077*
C115	0.0793 (10)	0.2279 (5)	1.1156 (4)	0.0792 (13)
H115	0.0718	0.1202	1.1222	0.095*
C113	0.2391 (9)	0.4563 (6)	1.1789 (4)	0.0734 (11)
H113	0.3422	0.5039	1.2280	0.088*
C114	0.2259 (9)	0.2964 (6)	1.1884 (4)	0.0774 (13)
H114	0.3183	0.2363	1.2450	0.093*
O72	−0.3587 (4)	0.7608 (3)	0.3218 (2)	0.0535 (5)
O92	0.2915 (4)	0.7852 (3)	0.8366 (3)	0.0554 (5)
O91	−0.0517 (4)	0.8944 (3)	0.9190 (3)	0.0591 (6)
O71	−0.0124 (5)	0.8698 (3)	0.3220 (3)	0.0637 (7)
C4	0.2004 (5)	0.5547 (3)	0.6269 (3)	0.0370 (5)
O21	0.3934 (4)	0.2806 (2)	0.7613 (2)	0.0473 (5)

	U11	U22	U33	U12	U13	U23
O33	0.0494 (13)	0.0492 (13)	0.0673 (15)	−0.0017 (11)	−0.0076 (11)	0.0051 (11)
Cl1	0.0759 (6)	0.0560 (5)	0.0586 (5)	0.0031 (4)	0.0241 (4)	−0.0061 (4)
Cl2	0.0741 (6)	0.0476 (4)	0.1050 (8)	−0.0204 (4)	0.0308 (5)	−0.0288 (5)
Cl3	0.0413 (4)	0.0946 (7)	0.0838 (6)	0.0154 (4)	−0.0058 (4)	−0.0032 (5)
N41	0.0439 (13)	0.0350 (11)	0.0398 (12)	0.0079 (10)	−0.0005 (9)	0.0012 (9)
C1	0.0375 (14)	0.0379 (14)	0.0531 (16)	−0.0024 (11)	0.0056 (11)	−0.0056 (11)
C7	0.0410 (14)	0.0435 (15)	0.0412 (14)	0.0029 (12)	−0.0024 (11)	0.0028 (11)
C9	0.0441 (14)	0.0397 (14)	0.0459 (15)	0.0077 (11)	−0.0048 (11)	0.0056 (12)
C3	0.0417 (14)	0.0403 (14)	0.0398 (13)	0.0013 (11)	0.0024 (10)	0.0017 (11)
C10	0.0375 (13)	0.0376 (13)	0.0444 (14)	0.0073 (11)	−0.0052 (11)	−0.0035 (11)
C5	0.0419 (14)	0.0338 (13)	0.0481 (15)	−0.0020 (10)	−0.0039 (11)	0.0043 (11)
C111	0.0480 (15)	0.0477 (16)	0.0385 (13)	0.0000 (13)	0.0078 (12)	−0.0018 (12)
C2	0.0349 (12)	0.0363 (13)	0.0440 (14)	0.0022 (10)	−0.0012 (10)	−0.0049 (10)
C6	0.0478 (16)	0.0414 (15)	0.0532 (16)	−0.0051 (12)	−0.0114 (13)	0.0081 (13)
C11	0.0387 (14)	0.0508 (17)	0.0516 (16)	0.0032 (12)	0.0001 (12)	−0.0028 (13)
C112	0.075 (2)	0.0510 (19)	0.0489 (17)	−0.0038 (17)	−0.0081 (16)	0.0032 (14)
C8	0.063 (2)	0.081 (3)	0.0495 (18)	0.0133 (19)	−0.0149 (15)	0.0064 (17)
C116	0.082 (3)	0.0495 (19)	0.059 (2)	−0.0072 (17)	0.0021 (18)	−0.0027 (15)
C115	0.115 (4)	0.049 (2)	0.069 (3)	0.007 (2)	0.006 (3)	0.0063 (18)
C113	0.084 (3)	0.085 (3)	0.052 (2)	−0.004 (2)	−0.0171 (19)	0.0069 (19)
C114	0.093 (3)	0.078 (3)	0.055 (2)	0.026 (2)	−0.002 (2)	0.013 (2)
O72	0.0482 (12)	0.0614 (14)	0.0511 (12)	−0.0012 (10)	−0.0121 (9)	0.0063 (10)
O92	0.0449 (12)	0.0501 (13)	0.0709 (14)	−0.0013 (10)	−0.0017 (10)	−0.0073 (11)
O91	0.0540 (13)	0.0445 (12)	0.0778 (16)	0.0107 (10)	−0.0050 (11)	−0.0166 (11)
O71	0.0538 (14)	0.0628 (15)	0.0738 (16)	−0.0076 (11)	−0.0098 (12)	0.0244 (12)
C4	0.0379 (12)	0.0331 (13)	0.0400 (13)	−0.0025 (10)	−0.0037 (10)	0.0014 (10)
O21	0.0524 (12)	0.0423 (11)	0.0432 (11)	0.0133 (9)	0.0038 (8)	0.0029 (9)

O33—H33B	0.87 (6)	C5—H5B	0.9700
O33—H33A	0.76 (6)	C111—C116	1.384 (5)
Cl1—C1	1.757 (3)	C111—C112	1.385 (5)
Cl2—C1	1.772 (3)	C111—C11	1.510 (4)
Cl3—C1	1.770 (3)	C2—O21	1.241 (4)
N41—C4	1.314 (4)	C6—H6A	0.9700
N41—C10	1.453 (3)	C6—H6B	0.9700
N41—H41	0.83 (5)	C11—H11A	0.9700
C1—C2	1.564 (4)	C11—H11B	0.9700
C7—O71	1.186 (4)	C112—C113	1.385 (5)
C7—O72	1.343 (4)	C112—H112	0.9300
C7—C6	1.500 (4)	C8—O72	1.448 (4)
C9—O91	1.209 (4)	C8—H8A	0.9600
C9—O92	1.303 (4)	C8—H8B	0.9600
C9—C10	1.523 (4)	C8—H8C	0.9600
C3—C2	1.397 (4)	C116—C115	1.393 (6)
C3—C4	1.401 (4)	C116—H116	0.9300
C3—H3	0.9300	C115—C114	1.344 (7)
C10—C11	1.545 (4)	C115—H115	0.9300
C10—H10	0.9800	C113—C114	1.382 (7)
C5—C4	1.509 (4)	C113—H113	0.9300
C5—C6	1.517 (4)	C114—H114	0.9300
C5—H5A	0.9700	O92—H92	0.89 (5)
H33B—O33—H33A	115 (6)	C7—C6—H6A	109.2
C4—N41—C10	126.9 (2)	C5—C6—H6A	109.2
C4—N41—H41	121 (4)	C7—C6—H6B	109.2
C10—N41—H41	112 (4)	C5—C6—H6B	109.2
C2—C1—Cl1	116.0 (2)	H6A—C6—H6B	107.9
C2—C1—Cl3	107.9 (2)	C111—C11—C10	113.8 (2)
Cl1—C1—Cl3	107.55 (16)	C111—C11—H11A	108.8
C2—C1—Cl2	107.0 (2)	C10—C11—H11A	108.8
Cl1—C1—Cl2	109.06 (17)	C111—C11—H11B	108.8
Cl3—C1—Cl2	109.22 (17)	C10—C11—H11B	108.8
O71—C7—O72	124.4 (3)	H11A—C11—H11B	107.7
O71—C7—C6	125.1 (3)	C111—C112—C113	120.9 (4)
O72—C7—C6	110.5 (2)	C111—C112—H112	119.6
O91—C9—O92	124.1 (3)	C113—C112—H112	119.6
O91—C9—C10	121.0 (3)	O72—C8—H8A	109.5
O92—C9—C10	114.9 (3)	O72—C8—H8B	109.5
C2—C3—C4	122.1 (3)	H8A—C8—H8B	109.5
C2—C3—H3	119.0	O72—C8—H8C	109.5
C4—C3—H3	119.0	H8A—C8—H8C	109.5
N41—C10—C9	113.6 (2)	H8B—C8—H8C	109.5
N41—C10—C11	110.4 (2)	C111—C116—C115	120.1 (4)
C9—C10—C11	111.3 (2)	C111—C116—H116	119.9
N41—C10—H10	107.1	C115—C116—H116	119.9
C9—C10—H10	107.1	C114—C115—C116	121.0 (4)
C11—C10—H10	107.1	C114—C115—H115	119.5
C4—C5—C6	110.9 (2)	C116—C115—H115	119.5
C4—C5—H5A	109.5	C114—C113—C112	119.7 (4)
C6—C5—H5A	109.5	C114—C113—H113	120.1
C4—C5—H5B	109.5	C112—C113—H113	120.1
C6—C5—H5B	109.5	C115—C114—C113	119.9 (4)
H5A—C5—H5B	108.0	C115—C114—H114	120.1
C116—C111—C112	118.3 (3)	C113—C114—H114	120.1
C116—C111—C11	120.3 (3)	C7—O72—C8	115.5 (3)
C112—C111—C11	121.4 (3)	C9—O92—H92	111 (3)
O21—C2—C3	125.9 (3)	N41—C4—C3	122.1 (2)
O21—C2—C1	115.3 (2)	N41—C4—C5	120.6 (2)
C3—C2—C1	118.7 (3)	C3—C4—C5	117.4 (2)
C7—C6—C5	112.0 (2)
C4—N41—C10—C9	−76.6 (4)	N41—C10—C11—C111	54.1 (3)
C4—N41—C10—C11	157.5 (3)	C9—C10—C11—C111	−73.0 (3)
O91—C9—C10—N41	178.7 (3)	C116—C111—C112—C113	1.9 (6)
O92—C9—C10—N41	−0.6 (4)	C11—C111—C112—C113	−178.7 (4)
O91—C9—C10—C11	−56.0 (3)	C112—C111—C116—C115	−1.1 (5)
O92—C9—C10—C11	124.7 (3)	C11—C111—C116—C115	179.5 (4)
C4—C3—C2—O21	−0.5 (5)	C111—C116—C115—C114	0.3 (7)
C4—C3—C2—C1	178.8 (3)	C111—C112—C113—C114	−1.9 (7)
Cl1—C1—C2—O21	−173.6 (2)	C116—C115—C114—C113	−0.3 (7)
Cl3—C1—C2—O21	−53.0 (3)	C112—C113—C114—C115	1.0 (7)
Cl2—C1—C2—O21	64.5 (3)	O71—C7—O72—C8	−0.8 (5)
Cl1—C1—C2—C3	7.0 (4)	C6—C7—O72—C8	−179.7 (3)
Cl3—C1—C2—C3	127.7 (3)	C10—N41—C4—C3	175.1 (3)
Cl2—C1—C2—C3	−114.9 (3)	C10—N41—C4—C5	−7.0 (4)
O71—C7—C6—C5	13.3 (5)	C2—C3—C4—N41	−2.2 (5)
O72—C7—C6—C5	−167.8 (3)	C2—C3—C4—C5	179.8 (3)
C4—C5—C6—C7	−168.9 (3)	C6—C5—C4—N41	−86.6 (3)
C116—C111—C11—C10	−115.5 (3)	C6—C5—C4—C3	91.4 (3)
C112—C111—C11—C10	65.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cl1i	0.97	2.94	3.774 (3)	145
O33—H33B···O91ii	0.87 (6)	1.89 (6)	2.766 (4)	177 (5)
N41—H41···O21	0.83 (5)	2.05 (6)	2.672 (3)	131 (5)
O33—H33A···O21iii	0.76 (6)	2.06 (6)	2.815 (3)	171 (6)
O92—H92···O33	0.89 (5)	1.66 (5)	2.542 (4)	175 (5)
C3—H3···Cl1	0.93	2.55	3.031 (3)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cl1i	0.97	2.94	3.774 (3)	145
O33—H33B⋯O91ii	0.87 (6)	1.89 (6)	2.766 (4)	177 (5)
N41—H41⋯O21	0.83 (5)	2.05 (6)	2.672 (3)	131 (5)
O33—H33A⋯O21iii	0.76 (6)	2.06 (6)	2.815 (3)	171 (6)
O92—H92⋯O33	0.89 (5)	1.66 (5)	2.542 (4)	175 (5)
C3—H3⋯Cl1	0.93	2.55	3.031 (3)	112

Symmetry codes: (i) ; (ii) ; (iii) .