(2R,3S)-2-Ammonio-3-hydr­oxy-3-(4-nitro­phen­yl)propanoic acid chloride monohydrate

Gaumet, V.; Weber, V.; Zaitsev, V.P.; Madesclaire, M.

doi:10.1107/S1600536808012750

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1003-o1004

doi:10.1107/S1600536808012750

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(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanoic acid chloride monohydrate

Vincent Gaumet,^a ^* Valérie Weber,^b Valery P. Zaitsev ^c and Michel Madesclaire ^b

^aLaboratoire de Chimie Physique, EA 4231, Faculté de Pharmacie, Université d'Auvergne, 63001 Clermont-Ferrand, France, ^bLaboratoire de Chimie Thérapeutique, EA 4231, Faculté de Pharmacie, Université d'Auvergne, 63001 Clermont-Ferrand, France, and ^cChimie Organique, Faculté de Chimie, 443011 Samara, Russian Federation
^*Correspondence e-mail: vincent.gaumet@u-clermont1.fr

(Received 10 April 2008; accepted 30 April 2008; online 7 May 2008)

The title compound, C₉H₁₁N₂O₅⁺·Cl⁻·H₂O, was synthesized from (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol in four steps. As demonstrated by this work, no racemization occurs during this synthetic procedure. The crystal structure displays many intermolecular hydrogen bonds between the acidic cation, chloride anions and the water molecules, forming a three-dimensional network. An intramolecular bond between the ammonium group and a hydroxyl O atom is also present.

Related literature

For related compounds see: Crich et al. (2007 ); Di Giovanni et al. (1996 ); Easton et al. (1996 ); Madesclaire et al. (2006 , 2007 ); Steinreiber et al. (2007 ); Zaitsev et al. (1998 ).

Experimental

Crystal data

C₉H₁₁N₂O₅⁺·Cl⁻·H₂O
M_r = 280.66
Monoclinic, P 2₁
a = 8.1286 (17) Å
b = 5.056 (3) Å
c = 15.848 (3) Å
β = 104.626 (17)°
V = 630.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 (2) K
0.49 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.872, T_max = 0.931
6026 measured reflections
5517 independent reflections
5058 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 63 reflections intensity decay: 3%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.09
5517 reflections
216 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.63 e Å⁻³
Absolute structure: Flack (1983 ), 2752 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H101⋯O13ⁱ	0.810 (17)	2.420 (16)	2.9259 (13)	121.5 (14)
N10—H101⋯Clⁱⁱ	0.810 (17)	2.489 (16)	3.2298 (11)	152.7 (15)
N10—H102⋯O14	0.83 (2)	2.265 (19)	2.6759 (14)	110.8 (16)
N10—H102⋯Clⁱⁱⁱ	0.83 (2)	2.62 (2)	3.3409 (14)	145.5 (16)
N10—H103⋯Cl^iv	0.97 (3)	2.28 (3)	3.2435 (14)	176 (3)
O12—H12⋯O17^v	0.78 (5)	1.84 (5)	2.6168 (19)	171 (4)
O14—H14⋯Cl	0.82 (3)	2.25 (3)	3.0539 (13)	166 (3)
O17—H171⋯O16^vi	0.78 (3)	2.33 (3)	3.069 (2)	159 (4)
O17—H172⋯Cl^vii	0.76 (3)	2.45 (3)	3.2170 (13)	178 (3)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+2]$ ; (ii) x-1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (v) $[-x, y+{\script{3\over 2}}, -z+1]$ ; (vi) x, y-1, z; (vii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012750/cs2076sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012750/cs2076Isup2.hkl

checkCIF report

Comment top

Preparation of new α-amino acids are of constant interest. (1S,2S) and (1R,2R)-2-amino-1- (4-nitrophenyl)-1,3-propanediols, byproducts in the manufacture of the antibiotic Chloramphenicol (Zaitsev et al., 1998), can be used as starting materials in the preparation of corresponding α-amino acid isomers. The title compound (V) was synthesized from (1S,2S)-2-amino-1- (4-nitrophenyl)-1,3-propanediol (I) in four steps according to Figure 1. The intermediate formation of the 2-oxazolidinone derivative (III) allowed to protect both the adjacent amino and hydroxyl groups (Di Giovanni et al., 1996; Crich et al., 2007). The absolute configuration, determined using anomalous dispersion by chlorine, confirms the R and S configurations respectively for C2 and C3 atoms, confirming that no racemization occurs during this synthetic route (note that the Cahn-Ingold-Prelog designation at the α-carbon of the hydroxyl group is reversed by comparison with that of the starting material due to the change in priority of the substituents). As expected, the phenyl ring is planar, r.m.s. deviation from the best plane is ca. 0.007Å. The nitro group is coplanar with the adjacent phenyl ring (O15—N11—C7—C8 = 0.2 (3)° and O16—N11—C7—C8 = 179.9 (2)°). However, the σ bond C7—N11 (1.4704 (17) Å) shows that there is no appreciable π delocalization in the bond between the sp² hybridized N11 and the phenyl ring.

Related literature top

For related compounds see: Crich et al. (2007); Di Giovanni et al. (1996); Easton et al. (1996); Madesclaire et al. (2006, 2007); Steinreiber et al. (2007); Zaitsev et al. (1998).

Experimental top

Figure 1 summarizes the synthetic route used (Madesclaire et al., 2006 and 2007). Crystals suitable for an X-ray diffraction study were obtained by slow evaporation of a water solution containing compound (V).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Synthesis of the title compound (V).
	Fig. 2. The molecular structure of the title compound (V), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 3. Crystal packing of the title compound. Intra and intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the interactions have been omitted.

(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanoic acid chloride monohydrate top

Crystal data top

C₉H₁₁N₂O₅⁺·Cl⁻·H₂O	F(000) = 292
M_r = 280.66	D_x = 1.479 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.1286 (17) Å	θ = 8–18°
b = 5.056 (3) Å	µ = 0.33 mm⁻¹
c = 15.848 (3) Å	T = 293 K
β = 104.626 (17)°	Elongated prism, colourless
V = 630.2 (4) Å³	0.49 × 0.25 × 0.20 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	5058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 35.0°, θ_min = 1.3°
ω/2θ scans	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
T_min = 0.872, T_max = 0.931	l = −25→25
6026 measured reflections	3 standard reflections every 63 reflections
5517 independent reflections	intensity decay: 3%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0825P)² + 0.0202P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max = 0.001
S = 1.09	Δρ_max = 0.60 e Å⁻³
5517 reflections	Δρ_min = −0.63 e Å⁻³
216 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.089 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2752 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (4)

Crystal data top

C₉H₁₁N₂O₅⁺·Cl⁻·H₂O	V = 630.2 (4) Å³
M_r = 280.66	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.1286 (17) Å	µ = 0.33 mm⁻¹
b = 5.056 (3) Å	T = 293 K
c = 15.848 (3) Å	0.49 × 0.25 × 0.20 mm
β = 104.626 (17)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	5058 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.022
T_min = 0.872, T_max = 0.931	3 standard reflections every 63 reflections
6026 measured reflections	intensity decay: 3%
5517 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	All H-atom parameters refined
wR(F²) = 0.115	Δρ_max = 0.60 e Å⁻³
S = 1.09	Δρ_min = −0.63 e Å⁻³
5517 reflections	Absolute structure: Flack (1983), 2752 Friedel pairs
216 parameters	Absolute structure parameter: 0.00 (4)
1 restraint

Special details top

Experimental. North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351. Number of psi-scan sets used was 4. Theta correction was applied. Weighted transmission curves were used. No Fourier smoothing was applied.

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

	x	y	z	U_iso*/U_eq
Cl	0.71520 (3)	0.93514 (6)	0.922526 (17)	0.03591 (8)
C1	−0.00336 (13)	1.2561 (2)	0.83505 (7)	0.02674 (16)
C2	0.09722 (12)	1.00092 (18)	0.85613 (6)	0.02405 (15)
C3	0.27337 (13)	1.0067 (2)	0.83713 (6)	0.02743 (16)
C4	0.26848 (14)	1.0458 (2)	0.74189 (7)	0.02986 (18)
C5	0.3717 (2)	1.2362 (3)	0.71889 (9)	0.0427 (3)
C6	0.3767 (3)	1.2672 (4)	0.63235 (10)	0.0499 (4)
C7	0.2774 (2)	1.1044 (3)	0.57084 (8)	0.0415 (3)
C8	0.1743 (2)	0.9107 (4)	0.59137 (9)	0.0506 (4)
C9	0.1720 (2)	0.8796 (3)	0.67820 (9)	0.0459 (3)
N10	0.12271 (11)	0.9477 (2)	0.95052 (5)	0.02702 (14)
N11	0.2786 (2)	1.1354 (4)	0.47874 (9)	0.0569 (4)
O12	−0.08726 (19)	1.2705 (3)	0.75327 (6)	0.0491 (3)
O13	−0.00519 (12)	1.42165 (18)	0.88974 (5)	0.03491 (16)
O14	0.34476 (13)	0.7557 (2)	0.86696 (7)	0.03708 (19)
O15	0.1882 (3)	0.9890 (7)	0.42545 (9)	0.0966 (9)
O16	0.3691 (3)	1.3062 (5)	0.45945 (10)	0.0847 (6)
H2	0.034 (3)	0.872 (5)	0.8304 (13)	0.037 (5)*
H3	0.343 (3)	1.127 (5)	0.8692 (13)	0.032 (5)*
H5	0.445 (3)	1.340 (6)	0.7648 (17)	0.052 (6)*
H6	0.453 (4)	1.424 (10)	0.620 (2)	0.091 (10)*
H8	0.112 (5)	0.807 (10)	0.548 (2)	0.087 (10)*
H9	0.090 (4)	0.766 (8)	0.6899 (19)	0.073 (9)*
H101	0.032 (2)	0.927 (4)	0.9615 (10)	0.025 (3)*
H102	0.186 (2)	0.816 (4)	0.9639 (12)	0.030 (4)*
H103	0.174 (4)	1.087 (7)	0.9905 (16)	0.058 (7)*
H12	−0.147 (5)	1.395 (10)	0.743 (2)	0.087 (10)*
H14	0.448 (3)	0.778 (6)	0.8856 (15)	0.049 (6)*
O17	0.29100 (18)	0.1787 (3)	0.26402 (8)	0.0491 (3)
H171	0.307 (4)	0.250 (8)	0.309 (2)	0.073 (9)*
H172	0.290 (3)	0.237 (6)	0.2194 (17)	0.053 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.03069 (11)	0.03544 (12)	0.03887 (13)	0.00116 (10)	0.00372 (8)	−0.00215 (10)
C1	0.0319 (4)	0.0221 (3)	0.0267 (4)	0.0005 (3)	0.0084 (3)	0.0022 (3)
C2	0.0281 (3)	0.0200 (3)	0.0249 (3)	−0.0009 (3)	0.0083 (3)	0.0000 (2)
C3	0.0288 (4)	0.0274 (4)	0.0276 (4)	−0.0040 (3)	0.0099 (3)	−0.0011 (3)
C4	0.0339 (4)	0.0297 (4)	0.0287 (4)	−0.0028 (3)	0.0130 (3)	−0.0025 (3)
C5	0.0576 (7)	0.0393 (6)	0.0359 (5)	−0.0182 (6)	0.0206 (5)	−0.0051 (4)
C6	0.0705 (10)	0.0481 (7)	0.0377 (6)	−0.0171 (7)	0.0260 (6)	−0.0004 (5)
C7	0.0531 (7)	0.0457 (7)	0.0295 (5)	0.0025 (5)	0.0176 (5)	0.0005 (4)
C8	0.0595 (8)	0.0634 (10)	0.0304 (5)	−0.0190 (8)	0.0141 (5)	−0.0110 (6)
C9	0.0582 (8)	0.0504 (8)	0.0323 (5)	−0.0227 (6)	0.0172 (5)	−0.0090 (5)
N10	0.0337 (3)	0.0226 (3)	0.0266 (3)	0.0022 (3)	0.0110 (2)	0.0036 (3)
N11	0.0739 (10)	0.0692 (11)	0.0324 (5)	−0.0018 (8)	0.0221 (6)	0.0009 (6)
O12	0.0684 (7)	0.0451 (5)	0.0274 (4)	0.0240 (5)	0.0005 (4)	0.0003 (4)
O13	0.0471 (4)	0.0216 (3)	0.0339 (3)	0.0039 (3)	0.0062 (3)	−0.0026 (3)
O14	0.0310 (4)	0.0371 (4)	0.0441 (5)	0.0061 (3)	0.0112 (3)	0.0058 (4)
O15	0.1309 (16)	0.127 (2)	0.0336 (5)	−0.0504 (17)	0.0250 (8)	−0.0151 (8)
O16	0.1330 (17)	0.0846 (12)	0.0465 (7)	−0.0305 (13)	0.0414 (9)	0.0055 (8)
O17	0.0652 (7)	0.0431 (5)	0.0357 (5)	−0.0145 (5)	0.0070 (4)	0.0004 (4)

Geometric parameters (Å, º) top

C1—O13	1.2078 (14)	C7—C8	1.380 (2)
C1—O12	1.3053 (14)	C7—N11	1.4704 (17)
C1—C2	1.5188 (15)	C8—C9	1.3898 (18)
C2—N10	1.4821 (12)	C8—H8	0.91 (4)
C2—C3	1.5360 (14)	C9—H9	0.94 (4)
C2—H2	0.87 (2)	N10—H101	0.810 (17)
C3—O14	1.4253 (16)	N10—H102	0.83 (2)
C3—C4	1.5128 (14)	N10—H103	0.97 (3)
C3—H3	0.90 (2)	N11—O15	1.219 (3)
C4—C5	1.3851 (17)	N11—O16	1.222 (3)
C4—C9	1.3931 (18)	O12—H12	0.78 (5)
C5—C6	1.3913 (19)	O14—H14	0.82 (3)
C5—H5	0.97 (3)	O17—H171	0.78 (3)
C6—C7	1.372 (2)	O17—H172	0.76 (3)
C6—H6	1.05 (4)

O13—C1—O12	125.15 (11)	C5—C6—H6	115.3 (17)
O13—C1—C2	122.31 (10)	C6—C7—C8	122.79 (12)
O12—C1—C2	112.53 (9)	C6—C7—N11	119.42 (14)
N10—C2—C1	107.85 (8)	C8—C7—N11	117.79 (14)
N10—C2—C3	107.55 (8)	C7—C8—C9	118.33 (14)
C1—C2—C3	114.68 (8)	C7—C8—H8	119 (3)
N10—C2—H2	104.6 (14)	C9—C8—H8	123 (3)
C1—C2—H2	108.4 (15)	C8—C9—C4	120.22 (13)
C3—C2—H2	113.1 (14)	C8—C9—H9	117.0 (19)
O14—C3—C4	110.69 (9)	C4—C9—H9	121.9 (19)
O14—C3—C2	103.87 (8)	C2—N10—H101	109.8 (11)
C4—C3—C2	114.02 (9)	C2—N10—H102	108.8 (13)
O14—C3—H3	105.5 (14)	H101—N10—H102	112 (2)
C4—C3—H3	109.3 (13)	C2—N10—H103	117.1 (17)
C2—C3—H3	113.1 (13)	H101—N10—H103	102 (2)
C5—C4—C9	119.76 (11)	H102—N10—H103	106 (2)
C5—C4—C3	119.24 (10)	O15—N11—O16	123.43 (16)
C9—C4—C3	120.81 (10)	O15—N11—C7	117.97 (18)
C4—C5—C6	120.54 (13)	O16—N11—C7	118.60 (17)
C4—C5—H5	118.4 (17)	C1—O12—H12	113 (2)
C6—C5—H5	120.9 (17)	C3—O14—H14	107 (2)
C7—C6—C5	118.32 (13)	H171—O17—H172	129 (4)
C7—C6—H6	126.2 (17)

O15—N11—C7—C6	−179.5 (2)	O14—C3—C4—C9	62.57 (15)
O16—N11—C7—C6	0.2 (3)	O14—C3—C4—C5	−112.37 (13)
O15—N11—C7—C8	0.2 (3)	C2—C3—C4—C9	−54.08 (14)
O16—N11—C7—C8	179.9 (2)	C5—C4—C9—C8	−2.4 (2)
O12—C1—C2—C3	84.78 (12)	C3—C4—C9—C8	−177.27 (13)
O12—C1—C2—N10	−155.44 (11)	C9—C4—C5—C6	1.6 (2)
O13—C1—C2—N10	23.39 (14)	C3—C4—C5—C6	176.57 (15)
O13—C1—C2—C3	−96.39 (12)	C4—C5—C6—C7	−0.2 (3)
C1—C2—C3—O14	176.50 (9)	C5—C6—C7—N11	179.19 (18)
C1—C2—C3—C4	−62.95 (11)	C5—C6—C7—C8	−0.5 (3)
N10—C2—C3—C4	177.11 (8)	C6—C7—C8—C9	−0.2 (3)
N10—C2—C3—O14	56.56 (10)	N11—C7—C8—C9	−179.96 (17)
C2—C3—C4—C5	130.98 (12)	C7—C8—C9—C4	1.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H101···O13ⁱ	0.810 (17)	2.420 (16)	2.9259 (13)	121.5 (14)
N10—H101···Clⁱⁱ	0.810 (17)	2.489 (16)	3.2298 (11)	152.7 (15)
N10—H102···O14	0.83 (2)	2.265 (19)	2.6759 (14)	110.8 (16)
N10—H102···Clⁱⁱⁱ	0.83 (2)	2.62 (2)	3.3409 (14)	145.5 (16)
N10—H103···Cl^iv	0.97 (3)	2.28 (3)	3.2435 (14)	176 (3)
O12—H12···O17^v	0.78 (5)	1.84 (5)	2.6168 (19)	171 (4)
O14—H14···Cl	0.82 (3)	2.25 (3)	3.0539 (13)	166 (3)
O17—H171···O16^vi	0.78 (3)	2.33 (3)	3.069 (2)	159 (4)
O17—H172···Cl^vii	0.76 (3)	2.45 (3)	3.2170 (13)	178 (3)

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

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₂O₅⁺·Cl⁻·H₂O
M_r	280.66
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	8.1286 (17), 5.056 (3), 15.848 (3)
β (°)	104.626 (17)
V (Å³)	630.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.49 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.872, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	6026, 5517, 5058
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.806

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.115, 1.09
No. of reflections	5517
No. of parameters	216
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.63
Absolute structure	Flack (1983), 2752 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H101···O13ⁱ	0.810 (17)	2.420 (16)	2.9259 (13)	121.5 (14)
N10—H101···Clⁱⁱ	0.810 (17)	2.489 (16)	3.2298 (11)	152.7 (15)
N10—H102···O14	0.83 (2)	2.265 (19)	2.6759 (14)	110.8 (16)
N10—H102···Clⁱⁱⁱ	0.83 (2)	2.62 (2)	3.3409 (14)	145.5 (16)
N10—H103···Cl^iv	0.97 (3)	2.28 (3)	3.2435 (14)	176 (3)
O12—H12···O17^v	0.78 (5)	1.84 (5)	2.6168 (19)	171 (4)
O14—H14···Cl	0.82 (3)	2.25 (3)	3.0539 (13)	166 (3)
O17—H171···O16^vi	0.78 (3)	2.33 (3)	3.069 (2)	159 (4)
O17—H172···Cl^vii	0.76 (3)	2.45 (3)	3.2170 (13)	178 (3)

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

References

Crich, D. & Li, W. (2007). J. Org. Chem. 72, 2387–2391. Web of Science CSD CrossRef PubMed CAS Google Scholar
Di Giovanni, M. C., Misiti, D., Villani, C. & Zappia, G. (1996). Tetrahedron Asymmetry, 7, 2277–2286. CrossRef CAS Google Scholar
Easton, C. J., Hutton, C. A., Merrett, M. C. & Tiekink, E. R. T. (1996). Tetrahedron, 52, 7025–7036. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harms, K. (1996). XCAD4. University of Marburg, Germany. Google Scholar
Madesclaire, M., Coudert, P., Zaitsev, V. P. & Zaitseva, J. V. (2006). Chem. Heterocycl. Compd. 42, 506–511. CrossRef CAS Google Scholar
Madesclaire, M., Zaitsev, V. P., Zaitseva, J. V. & Sharipova, S. Kh. (2007). Chem. Heterocycl. Compd. 43, 1325–1332. CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steinreiber, J., Fesko, K., Reisinger, C., Schürmann, M., van Assema, F., Wolberg, M., Mink, D. & Griengl, H. (2007). Tetrahedron, 63, 918–926. Web of Science CrossRef CAS Google Scholar
Zaitsev, V. P., Sharipova, S. Kh. & Zhuravleva, I. I. (1998). Pharm. Chem. J. 32, 157–160. CrossRef Google Scholar

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Volume 64| Part 6| June 2008| Pages o1003-o1004

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

(2R,3S)-2-Ammonio-3-hydr­­oxy-3-(4-nitro­phen­yl)propanoic acid chloride monohydrate

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Experimental

Crystal data

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organic compounds

(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanoic acid chloride monohydrate