(2R,3S)-2-Ammonio-3-hydr-oxy-3-(4-nitro-phen-yl)propanoic acid chloride monohydrate.

The title compound, C(9)H(11)N(2)O(5) (+)·Cl(-)·H(2)O, was synthesized from (1S,2S)-2-amino-1-(4-nitro-phen-yl)propane-1,3-diol in four steps. As demonstrated by this work, no racemization occurs during this synthetic procedure. The crystal structure displays many inter-molecular hydrogen bonds between the acidic cation, chloride anions and the water mol-ecules, forming a three-dimensional network. An intra-molecular 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 = 280.66

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.09

5517 reflections

216 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.60 e Å−3

Δρmin = −0.63 e Å−3

Absolute structure: Flack (1983 ▶), 2752 Friedel pairs

Flack parameter: 0.00 (4)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11N2O5+·Cl–·H2O	F000 = 292
Mr = 280.66	Dx = 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 = 8–18º
b = 5.056 (3) Å	µ = 0.33 mm−1
c = 15.848 (3) Å	T = 293 (2) K
β = 104.626 (17)º	Elongated prism, colourless
V = 630.2 (4) Å3	0.49 × 0.25 × 0.20 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 35.0º
Monochromator: graphite	θmin = 1.3º
T = 293(2) K	h = −13→13
ω/2θ scans	k = −8→8
Absorption correction: ψ scan(North et al., 1968)	l = −25→25
Tmin = 0.872, Tmax = 0.931	3 standard reflections
6026 measured reflections	every 63 reflections
5517 independent reflections	intensity decay: 3%
5058 reflections with I > 2σ(I)

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(Fo2) + (0.0825P)2 + 0.0202P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.60 e Å−3
5517 reflections	Δρmin = −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	Flack parameter: 0.00 (4)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cliv	0.97 (3)	2.28 (3)	3.2435 (14)	176 (3)
O12—H12···O17v	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···O16vi	0.78 (3)	2.33 (3)	3.069 (2)	159 (4)
O17—H172···Clvii	0.76 (3)	2.45 (3)	3.2170 (13)	178 (3)

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⋯Cliv	0.97 (3)	2.28 (3)	3.2435 (14)	176 (3)
O12—H12⋯O17v	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⋯O16vi	0.78 (3)	2.33 (3)	3.069 (2)	159 (4)
O17—H172⋯Clvii	0.76 (3)	2.45 (3)	3.2170 (13)	178 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .