(S,Z)-3-Phenyl-2-[(1,1,1-tri­chloro-7-meth­oxy-2,7-dioxohept-3-en-4-yl)amino]­propanoic acid monohydrate

Flores, A.F.C.; Vicenti, J.R. de M.; Pizzuti, L.; Campos, P.T.

doi:10.1107/S1600536814000154

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o169-o170

doi:10.1107/S1600536814000154

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(S,Z)-3-Phenyl-2-[(1,1,1-trichloro-7-methoxy-2,7-dioxohept-3-en-4-yl)amino]propanoic acid monohydrate

Alex Fabiani Claro Flores,^a ^* Juliano Rosa de Menezes Vicenti,^a Lucas Pizzuti ^b and Patrick Teixeira Campos ^c

^aEscola de Quimica e Alimentos, Universidade Federal do Rio Grande, Av. Italia, km 08, Campus Carreiros, 96203-900 Rio Grande, RS, Brazil, ^bUniversidade Federal da Grande Dourados, UFGD, CEP 79825-070 Dourados, MS, Brazil, and ^cInstituto Federal Farroupilha, Campus Júlio de Castilhos, CEP 98130-000, Júlio de Castilhos, RS, Brazil
^*Correspondence e-mail: alexflores@furg.br

(Received 11 December 2013; accepted 3 January 2014; online 18 January 2014)

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

CCDC reference: 979612

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_r = 440.69
Triclinic, P 1
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.04
6020 reflections
256 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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)

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) x-1, y, z; (ii) x+1, y, z; (iii) x, y+1, z.

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 ).

Supporting information

CCDC reference: 979612

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

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

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

checkCIF report

Comment top

Dielectrophiles derived from levulinic acid (Hachuła et al., 2013; Lo & Ng, 2008) belong to an important class of organic synthetic intermediates for the synthesis of a variety of heterocyclic compounds. Such precursors are used to produce pyrrolidinones, pyrrolones, pyrazoles and pyrimidines with very interesting biological activities (Flores et al., 2008; Flores et al., 2013). As a part of our studies, we report in this paper the crystal structure of (S,Z)-3-phenyl-2-(1,1,1-trichloro-7–2,7-dioxo-3-hepten- 4-ylamine)propanoic acid, obtained from the reaction between methyl 7,7,7-trichloro-4-methoxy-6-oxo-3-heptenoate and L-phenylalanine.

In the crystal structure of the title compound, the asymmetric unit is composed of the whole chiral organic molecule, C₁₇H₁₈Cl₃NO₅, connected to a water molecule (Fig.1). This connection consists of a short intermolecular hydrogen bond interaction involving the hydrogen atom of the carboxylic acid fragment [O92—H92···O33, 2.542 (4) Å; Pojarová et al., 2010]. Additionally, S(6) and S(5) ring motifs are formed by two distinct intramolecular hydrogen bonding systems, N41—H41···O21 [2.672 (3) Å] and C3—H3···Cl1 [3.031 (3) Å], respectively, thereby stabilizing the structure (da Costa et al., 2013).

There is also a weak C6—H6A···Cl1ⁱ intermolecular interaction [3.774 (3) Å] connecting organic molecules along the [100] crystallographic direction. The water molecules act as a bridging element in the crystal structure by expanding its dimensionality in both [100] and [010] crystallographic directions. The intermolecular hydrogen bond interactions generate bidimensional layers parallel to the ab plane. Each atom of the water molecule is connected to different groups on adjacent organic molecules: carboxylic acid [O92—H92···O33, 2.542 (4) Å and O33—H33B···O91ⁱⁱ, 2.766 (4) Å] and ketone [O33—H33A···O21ⁱⁱⁱ, 2.815 (3) Å]. Symmetry codes: (i) x–1, y, z; (ii) x + 1, y, z; (iii) x, y + 1, z. A super cell central projection of the crystal structure can be viewed in Fig. 2, which depicts a crystal packing diagram as viewed along the crystallographic a axis.

Related literature top

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 top

To a stirred solution of methyl 7,7,7-trichloro-4-methoxy-6-oxo-3-heptenoate (5 mmol, 1.52 g) and L-phenylalanine (5.5 mmol, 0.91 g), at 25 °C, was added a solution of 1 mol·L^-1 NaOH. There was an immediate formation of a yellow precipitate and the mixture was further stirred for 30 minutes. A solution of 50% HCl was added until the pH ≈ 1, when there was complete precipitation of the yellow solid. The solid was extracted with ethyl acetate, and this solution was dried over anhydrous MgSO₄. The ethyl acetate was removed on a rotary evaporator to give the product as a yellow solid. Yield: 79%. m. p. 120 – 123 °C. ¹H NMR (400 MHz, DMSO-D₆, TMS): δ 2.17 (m, 2H, CH₂), 2.44 (m, 2H, CH₂), 3.06 (dd, 1H, ³J=9.1 Hz, ²J=14 Hz, CH₂Ph), 3.37 (dd, 1H, ³J=9.1 Hz, ²J=14 Hz, CH₂Ph), 3.66 (s, 3H, OMe), 4.53 (m, 1H, CH_chiral), 5.60 (s, 1H, =CH), 7.22–7.33 (m, 5H, Ph), 10.9 (d, 1H, ³J = 10 Hz, NH) p.p.m.; ¹³C NMR (100 MHz, DMSO-D₆): δ 26.8, 31.5, 39.9, 52.2, 58.1, 86.0, 96.9, 127.5, 128.9, 129.5, 135.4, 169.9, 172.0, 173.2, 181.2 p.p.m.. Crystals were grown from a methanol solution, which was slowly evaporated at room temperature.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. An ellipsoid plot (50% probability) showing the asymmetric unit. Hydrogen bonds are represented as dashed lines. Symmetry codes: (i) x–1, y, z; (ii) x + 1, y, z; (iii) x, y + 1, z.
	Fig. 2. Packing of molecules along the [100] direction through intermolecular hydrogen bonds, represented with dashed lines. Some hydrogen atoms were omitted for clarity.

(S,Z)-3-Phenyl-2-[(1,1,1-trichloro-7-methoxy-2,7-dioxohept-3-en-4-yl)amino]propanoic acid monohydrate top

Crystal data top

C₁₇H₁₈Cl₃NO₅·H₂O	F(000) = 228
M_r = 440.69	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0502P)² + 0.0376P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.41 e Å⁻³
6020 reflections	Δρ_min = −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)

Crystal data top

C₁₇H₁₈Cl₃NO₅·H₂O	γ = 85.649 (17)°
M_r = 440.69	V = 500.8 (2) Å³
Triclinic, P1	Z = 1
a = 5.6684 (16) Å	Mo Kα radiation
b = 8.601 (3) Å	µ = 0.49 mm⁻¹
c = 10.336 (3) Å	T = 296 K
α = 87.720 (19)°	0.98 × 0.30 × 0.12 mm
β = 85.696 (17)°

Data collection top

Bruker APEXII CCD diffractometer	6020 independent reflections
Absorption correction: gaussian (XPREP; Bruker, 2006)	4784 reflections with I > 2σ(I)
T_min = 0.881, T_max = 1	R_int = 0.024
13424 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	Δρ_max = 0.41 e Å⁻³
S = 1.04	Δρ_min = −0.32 e Å⁻³
6020 reflections	Absolute structure: Flack parameter determined using 1984 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
256 parameters	Absolute structure parameter: 0.04 (2)
3 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) x+1, y, z; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cl1ⁱ	0.97	2.94	3.774 (3)	144.9
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)	112.3

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

Acknowledgements

The authors are grateful for financial support from the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Universal grant 6577818477962764–01), the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS, PqG grant 1016236) and the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES-PROEX).

References

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Volume 70| Part 2| February 2014| Pages o169-o170

doi:10.1107/S1600536814000154

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

(S,Z)-3-Phenyl-2-[(1,1,1-tri­chloro-7-meth­­oxy-2,7-dioxohept-3-en-4-yl)amino]­propanoic acid monohydrate

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organic compounds

(S,Z)-3-Phenyl-2-[(1,1,1-trichloro-7-methoxy-2,7-dioxohept-3-en-4-yl)amino]propanoic acid monohydrate