[(2R,3R)-3-(4-Nitro-phen-yl)aziridin-2-yl]methanol monohydrate.

The title monohydrate, C9H10N2O3·H2O, contains an aziridine ring including two contiguous stereocenters, both of which exhibit an R configuration. The methyl-hydroxy and nitro-phenyl groups are cis-disposed about the aziridine ring. The mean plane of the benzene ring is tilted to the aziridine ring by 66.65 (8)°. The nitro group is nearly coplanar with the benzene ring [dihedral angle = 2.5 (2)°]. In the crystal, the components are linked by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, generating supra-molecular layers parallel to (001).

Related literature

For the biological activity of aziridine derivatives, see: Li et al. (1995 ▶); Sheldon et al. (1999 ▶); n class="Chemical">Danshiitsoodol et al. (2006 ▶); Vicik et al. (2006 ▶); Keniche et al. (2011 ▶); Lee et al. (1992 ▶); Ngo et al. (1998 ▶). For the use of chiral aziridines as precursors for pharmaceutical products, see: Kim et al. (2001 ▶). For related structures, see: Zhu et al. (2006 ▶). For details of the synthesis, see: Madesclaire et al. (2013 ▶). For determination of the absolute configuration, see: Hooft et al. (2008 ▶).

Experimental

Crystal data

C9H10N2O3·n class="Chemical">H2O

M = 212.21

Monoclinic,

a = 6.3064 (2) Å

b = 5.4695 (2) Å

c = 14.6481 (5) Å

β = 94.303 (2)°

V = 503.83 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.68 × 0.44 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.944, T max = 1.000

5357 measured reflections

2383 independent reflections

2031 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.04

2383 reflections

152 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013391/kp2453sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013391/kp2453Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013391/kp2453Isup3.cml

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

C9H10N2O3·H2O	F(000) = 224
Mr = 212.21	Dx = 1.399 Mg m−3
Monoclinic, P21	Melting point: 379 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.3064 (2) Å	Cell parameters from 98 reflections
b = 5.4695 (2) Å	θ = 5.1–26.3°
c = 14.6481 (5) Å	µ = 0.11 mm−1
β = 94.303 (2)°	T = 296 K
V = 503.83 (3) Å3	Plate, colourless
Z = 2	0.68 × 0.44 × 0.06 mm

Bruker APEXII CCD diffractometer	2383 independent reflections
Radiation source: fine-focus sealed tube	2031 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 29.1°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −8→7
Tmin = 0.944, Tmax = 1.000	k = −7→6
5357 measured reflections	l = −20→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.0307P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2383 reflections	Δρmax = 0.13 e Å−3
152 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: The absolute configuration was assigned to agree with that of its precusor at the chiral center C2.
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
N1	0.6266 (2)	0.3667 (2)	0.33556 (10)	0.0457 (3)
H1	0.573 (3)	0.212 (5)	0.3340 (14)	0.063 (6)*
C2	0.4417 (2)	0.5260 (3)	0.34835 (10)	0.0394 (3)
H2	0.3069	0.4423	0.3563	0.047*
C3	0.5261 (2)	0.5024 (3)	0.25666 (9)	0.0394 (3)
H3	0.4388	0.4018	0.2131	0.047*
C4	0.4863 (3)	0.7468 (3)	0.40646 (10)	0.0397 (3)
H4A	0.4745	0.7051	0.4702	0.048*
H4B	0.6303	0.8024	0.3998	0.048*
O5	0.3410 (2)	0.9368 (2)	0.38063 (8)	0.0489 (3)
H5	0.256 (3)	0.927 (4)	0.4181 (12)	0.051 (5)*
C6	0.6449 (2)	0.7016 (3)	0.21394 (9)	0.0357 (3)
C7	0.8526 (2)	0.7649 (3)	0.24213 (10)	0.0426 (4)
H7	0.9250	0.6782	0.2894	0.051*
C8	0.9530 (2)	0.9552 (3)	0.20089 (9)	0.0422 (4)
H8	1.0915	0.9990	0.2205	0.051*
C9	0.8439 (2)	1.0790 (3)	0.13006 (9)	0.0361 (3)
C10	0.6386 (2)	1.0188 (3)	0.09979 (9)	0.0408 (4)
H10	0.5676	1.1043	0.0519	0.049*
C11	0.5409 (2)	0.8300 (3)	0.14185 (9)	0.0401 (4)
H11	0.4025	0.7871	0.1218	0.048*
N12	0.9485 (2)	1.2823 (3)	0.08617 (8)	0.0438 (3)
O13	1.13280 (19)	1.3298 (3)	0.11207 (9)	0.0642 (4)
O14	0.8479 (2)	1.3952 (3)	0.02591 (8)	0.0611 (4)
O1W	0.9400 (2)	0.4031 (3)	0.47803 (9)	0.0568 (3)
H1W	0.856 (4)	0.392 (5)	0.4262 (14)	0.089 (8)*
H2W	0.990 (4)	0.252 (4)	0.491 (2)	0.092 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0548 (8)	0.0273 (7)	0.0541 (8)	0.0025 (6)	−0.0019 (6)	0.0015 (6)
C2	0.0401 (8)	0.0322 (8)	0.0459 (7)	−0.0037 (6)	0.0026 (6)	0.0051 (7)
C3	0.0425 (8)	0.0338 (8)	0.0408 (7)	−0.0033 (7)	−0.0047 (6)	−0.0053 (6)
C4	0.0506 (9)	0.0344 (8)	0.0341 (7)	0.0016 (7)	0.0025 (6)	0.0029 (6)
O5	0.0594 (7)	0.0371 (6)	0.0511 (6)	0.0079 (6)	0.0090 (6)	0.0079 (6)
C6	0.0374 (7)	0.0395 (8)	0.0298 (6)	0.0015 (6)	0.0000 (5)	−0.0076 (6)
C7	0.0364 (7)	0.0519 (10)	0.0384 (7)	0.0040 (7)	−0.0054 (6)	0.0057 (8)
C8	0.0305 (7)	0.0553 (10)	0.0399 (7)	−0.0006 (7)	−0.0035 (5)	0.0013 (8)
C9	0.0368 (7)	0.0430 (8)	0.0288 (6)	0.0017 (6)	0.0048 (5)	−0.0038 (6)
C10	0.0390 (8)	0.0537 (10)	0.0288 (6)	0.0047 (7)	−0.0030 (5)	0.0015 (7)
C11	0.0325 (7)	0.0546 (10)	0.0322 (7)	−0.0012 (7)	−0.0044 (5)	−0.0036 (7)
N12	0.0453 (7)	0.0488 (9)	0.0373 (6)	−0.0046 (6)	0.0044 (5)	−0.0043 (6)
O13	0.0530 (7)	0.0721 (9)	0.0658 (8)	−0.0226 (7)	−0.0060 (6)	0.0051 (7)
O14	0.0650 (8)	0.0656 (9)	0.0518 (6)	−0.0047 (7)	−0.0025 (5)	0.0195 (6)
O1W	0.0527 (7)	0.0553 (8)	0.0612 (7)	−0.0004 (6)	−0.0036 (6)	−0.0010 (7)

N1—C3	1.476 (2)	C7—C8	1.381 (2)
N1—C2	1.479 (2)	C7—H7	0.9300
N1—H1	0.91 (2)	C8—C9	1.379 (2)
C2—C3	1.487 (2)	C8—H8	0.9300
C2—C4	1.492 (2)	C9—C10	1.377 (2)
C2—H2	0.9800	C9—N12	1.466 (2)
C3—C6	1.487 (2)	C10—C11	1.372 (2)
C3—H3	0.9800	C10—H10	0.9300
C4—O5	1.4181 (19)	C11—H11	0.9300
C4—H4A	0.9700	N12—O14	1.2161 (17)
C4—H4B	0.9700	N12—O13	1.2231 (16)
O5—H5	0.798 (19)	O1W—H1W	0.895 (19)
C6—C7	1.387 (2)	O1W—H2W	0.90 (2)
C6—C11	1.3907 (19)
C3—N1—C2	60.44 (10)	C7—C6—C11	118.73 (14)
C3—N1—H1	108.1 (13)	C7—C6—C3	123.49 (13)
C2—N1—H1	104.8 (14)	C11—C6—C3	117.77 (13)
N1—C2—C3	59.67 (10)	C8—C7—C6	120.79 (13)
N1—C2—C4	115.62 (13)	C8—C7—H7	119.6
C3—C2—C4	121.37 (12)	C6—C7—H7	119.6
N1—C2—H2	116.0	C9—C8—C7	118.67 (13)
C3—C2—H2	116.0	C9—C8—H8	120.7
C4—C2—H2	116.0	C7—C8—H8	120.7
N1—C3—C6	119.88 (13)	C10—C9—C8	121.95 (14)
N1—C3—C2	59.88 (10)	C10—C9—N12	118.91 (13)
C6—C3—C2	122.85 (12)	C8—C9—N12	119.14 (13)
N1—C3—H3	114.5	C11—C10—C9	118.58 (13)
C6—C3—H3	114.5	C11—C10—H10	120.7
C2—C3—H3	114.5	C9—C10—H10	120.7
O5—C4—C2	110.52 (12)	C10—C11—C6	121.27 (13)
O5—C4—H4A	109.5	C10—C11—H11	119.4
C2—C4—H4A	109.5	C6—C11—H11	119.4
O5—C4—H4B	109.5	O14—N12—O13	123.31 (15)
C2—C4—H4B	109.5	O14—N12—C9	118.43 (13)
H4A—C4—H4B	108.1	O13—N12—C9	118.25 (13)
C4—O5—H5	102.8 (15)	H1W—O1W—H2W	107 (2)
C3—N1—C2—C4	−112.85 (14)	C6—C7—C8—C9	−1.0 (2)
C2—N1—C3—C6	112.95 (15)	C7—C8—C9—C10	0.2 (2)
C4—C2—C3—N1	103.31 (15)	C7—C8—C9—N12	179.60 (14)
N1—C2—C3—C6	−108.12 (15)	C8—C9—C10—C11	0.1 (2)
C4—C2—C3—C6	−4.8 (2)	N12—C9—C10—C11	−179.30 (13)
N1—C2—C4—O5	152.10 (12)	C9—C10—C11—C6	0.4 (2)
C3—C2—C4—O5	83.41 (17)	C7—C6—C11—C10	−1.1 (2)
N1—C3—C6—C7	2.3 (2)	C3—C6—C11—C10	178.98 (14)
C2—C3—C6—C7	73.8 (2)	C10—C9—N12—O14	1.9 (2)
N1—C3—C6—C11	−177.77 (13)	C8—C9—N12—O14	−177.50 (14)
C2—C3—C6—C11	−106.31 (16)	C10—C9—N12—O13	−178.12 (14)
C11—C6—C7—C8	1.4 (2)	C8—C9—N12—O13	2.5 (2)
C3—C6—C7—C8	−178.68 (14)	C2—C4—O5—H5	99.5 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.91 (2)	2.24 (2)	3.064 (2)	150.0 (19)
O5—H5···O1Wii	0.798 (19)	2.03 (2)	2.8303 (19)	175.0 (17)
O1W—H1W···N1	0.90 (2)	1.89 (2)	2.772 (2)	167 (2)
O1W—H2W···O1Wiii	0.90 (2)	2.00 (2)	2.8971 (9)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.91 (2)	2.24 (2)	3.064 (2)	150.0 (19)
O5—H5⋯O1W ii	0.798 (19)	2.03 (2)	2.8303 (19)	175.0 (17)
O1W—H1W⋯N1	0.90 (2)	1.89 (2)	2.772 (2)	167 (2)
O1W—H2W⋯O1W iii	0.90 (2)	2.00 (2)	2.8971 (9)	172 (3)

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