(E)-tert-Butyl 4-(N'-hy-droxy-carbam--imid-o-yl)piperazine-1-carboxyl-ate.

In the title compound, C10H20N4O3, the piperazine ring adopts a chair conformation. The mol-ecule adopts an E conformation across the C=N double bond, with the -OH group and the piperazine ring trans to one another. Further, the H atom of the hy-droxy group is directed away from the NH2 group. An intra-molecular N-H⋯O contact occurs involving the NH2 group and the oxime O atom. In the crystal, mol-ecules are linked via strong N-H⋯O and O-H⋯N hydrogen bonds with alternating R2(2)(6) and C(9) motifs into tetra-meric units forming R4(4)(28) motifs.

Related literature

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a ▶,b ▶); Willems & Ilzerman (2010 ▶). For a related structure, see: Gowda et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C10H20N4O3

M = 244.3

Triclinic,

a = 8.1923 (17) Å

b = 8.7859 (16) Å

c = 9.714 (2) Å

α = 109.451 (7)°

β = 99.540 (7)°

γ = 96.474 (7)°

V = 639.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 300 K

0.22 × 0.16 × 0.1 mm

Data collection

Bruker SMART X2S diffractometer

6407 measured reflections

2218 independent reflections

1632 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.05

2218 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046223/zj2096sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046223/zj2096Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046223/zj2096Isup3.cml

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

C10H20N4O3	F(000) = 264
Mr = 244.3	prism
Triclinic, P1	Dx = 1.269 Mg m−3
Hall symbol: -P 1	Melting point: 463 K
a = 8.1923 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7859 (16) Å	Cell parameters from 1632 reflections
c = 9.714 (2) Å	θ = 25°
α = 109.451 (7)°	µ = 0.10 mm−1
β = 99.540 (7)°	T = 300 K
γ = 96.474 (7)°	Prism, colorless
V = 639.5 (2) Å3	0.22 × 0.16 × 0.1 mm
Z = 2

Bruker SMART X2S diffractometer	1632 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
multi–scan	h = −9→9
6407 measured reflections	k = −10→10
2218 independent reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0714P)2 + 0.0663P] where P = (Fo2 + 2Fc2)/3
2218 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3
0 constraints

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
C8	−0.0609 (3)	0.4383 (3)	0.7235 (3)	0.0705 (7)
H8A	−0.1504	0.3592	0.7258	0.106*
H8B	0.0275	0.4655	0.8107	0.106*
H8C	−0.0177	0.3931	0.6354	0.106*
C7	−0.1275 (2)	0.5921 (2)	0.7215 (2)	0.0452 (5)
O3	0.02502 (15)	0.69800 (15)	0.71797 (16)	0.0449 (4)
C6	0.0186 (2)	0.8470 (2)	0.7099 (2)	0.0363 (4)
N4	0.17149 (18)	0.92339 (18)	0.70828 (17)	0.0379 (4)
C3	0.3293 (2)	0.8718 (2)	0.7533 (2)	0.0386 (5)
H3A	0.3094	0.7539	0.7291	0.046*
H3B	0.3705	0.9241	0.8606	0.046*
C2	0.4601 (2)	0.9178 (2)	0.6738 (2)	0.0426 (5)
H2A	0.5652	0.8871	0.7081	0.051*
H2B	0.423	0.8574	0.5672	0.051*
N3	0.48827 (18)	1.09515 (18)	0.70205 (16)	0.0380 (4)
C1	0.5834 (2)	1.1978 (2)	0.8426 (2)	0.0372 (5)
C10	−0.1871 (3)	0.6755 (3)	0.8630 (3)	0.0710 (7)
H10A	−0.2858	0.6076	0.866	0.106*
H10B	−0.2133	0.7796	0.864	0.106*
H10C	−0.0999	0.6921	0.9486	0.106*
O2	−0.10816 (16)	0.90611 (16)	0.70148 (16)	0.0489 (4)
N2	0.7249 (2)	1.1515 (2)	0.8972 (2)	0.0500 (5)
C5	0.3302 (2)	1.1390 (2)	0.6480 (2)	0.0437 (5)
H5A	0.2963	1.083	0.5405	0.052*
H5B	0.3481	1.2561	0.6682	0.052*
C4	0.1884 (2)	1.0956 (2)	0.7193 (2)	0.0422 (5)
H4A	0.2114	1.1666	0.8236	0.051*
H4B	0.0835	1.1134	0.6693	0.051*
C9	−0.2609 (3)	0.5532 (3)	0.5819 (3)	0.0623 (6)
H9A	−0.3586	0.4846	0.5859	0.093*
H9B	−0.2185	0.4968	0.496	0.093*
H9C	−0.2907	0.6533	0.5747	0.093*
O1	0.6559 (2)	1.42316 (18)	1.05009 (17)	0.0655 (5)
H1	0.6236	1.5071	1.0951	0.098*
N1	0.5327 (2)	1.33013 (19)	0.91361 (19)	0.0483 (5)
H2C	0.776 (3)	1.084 (3)	0.835 (3)	0.061 (7)*
H2D	0.789 (3)	1.232 (3)	0.986 (3)	0.076 (8)*

	U11	U22	U33	U12	U13	U23
C8	0.0538 (14)	0.0579 (14)	0.113 (2)	0.0029 (12)	0.0172 (14)	0.0500 (15)
C7	0.0329 (10)	0.0476 (12)	0.0584 (13)	−0.0013 (9)	0.0116 (9)	0.0252 (10)
O3	0.0339 (7)	0.0396 (8)	0.0685 (9)	0.0052 (6)	0.0167 (7)	0.0264 (7)
C6	0.0348 (10)	0.0372 (10)	0.0377 (10)	0.0091 (8)	0.0113 (8)	0.0119 (8)
N4	0.0307 (8)	0.0338 (8)	0.0539 (10)	0.0079 (6)	0.0134 (7)	0.0191 (7)
C3	0.0327 (10)	0.0316 (10)	0.0541 (12)	0.0074 (8)	0.0106 (9)	0.0176 (9)
C2	0.0378 (11)	0.0360 (10)	0.0500 (12)	0.0067 (8)	0.0149 (9)	0.0077 (9)
N3	0.0399 (9)	0.0358 (9)	0.0411 (9)	0.0045 (7)	0.0144 (7)	0.0153 (7)
C1	0.0357 (10)	0.0344 (10)	0.0457 (11)	0.0046 (8)	0.0150 (9)	0.0173 (9)
C10	0.0646 (15)	0.0950 (19)	0.0633 (15)	0.0070 (14)	0.0278 (13)	0.0369 (14)
O2	0.0332 (8)	0.0476 (8)	0.0696 (10)	0.0143 (6)	0.0153 (7)	0.0214 (7)
N2	0.0422 (10)	0.0483 (11)	0.0554 (12)	0.0131 (9)	0.0093 (9)	0.0125 (9)
C5	0.0481 (12)	0.0424 (11)	0.0436 (11)	0.0037 (9)	0.0060 (9)	0.0225 (9)
C4	0.0390 (11)	0.0326 (10)	0.0571 (12)	0.0106 (8)	0.0091 (9)	0.0182 (9)
C9	0.0512 (13)	0.0536 (13)	0.0695 (16)	−0.0039 (11)	0.0003 (12)	0.0164 (12)
O1	0.0646 (10)	0.0469 (9)	0.0624 (10)	0.0096 (8)	−0.0060 (8)	0.0004 (7)
N1	0.0436 (10)	0.0355 (9)	0.0547 (11)	0.0041 (8)	0.0012 (8)	0.0073 (8)

C8—C7	1.517 (3)	N3—C5	1.457 (2)
C8—H8A	0.96	C1—N1	1.292 (2)
C8—H8B	0.96	C1—N2	1.356 (3)
C8—H8C	0.96	C10—H10A	0.96
C7—O3	1.484 (2)	C10—H10B	0.96
C7—C9	1.506 (3)	C10—H10C	0.96
C7—C10	1.515 (3)	N2—H2C	0.89 (3)
O3—C6	1.343 (2)	N2—H2D	0.94 (3)
C6—O2	1.216 (2)	C5—C4	1.522 (3)
C6—N4	1.358 (2)	C5—H5A	0.97
N4—C3	1.465 (2)	C5—H5B	0.97
N4—C4	1.470 (2)	C4—H4A	0.97
C3—C2	1.514 (3)	C4—H4B	0.97
C3—H3A	0.97	C9—H9A	0.96
C3—H3B	0.97	C9—H9B	0.96
C2—N3	1.473 (2)	C9—H9C	0.96
C2—H2A	0.97	O1—N1	1.447 (2)
C2—H2B	0.97	O1—H1	0.82
N3—C1	1.398 (2)
C7—C8—H8A	109.5	C5—N3—C2	108.79 (15)
C7—C8—H8B	109.5	N1—C1—N2	123.51 (19)
H8A—C8—H8B	109.5	N1—C1—N3	119.03 (17)
C7—C8—H8C	109.5	N2—C1—N3	117.45 (17)
H8A—C8—H8C	109.5	C7—C10—H10A	109.5
H8B—C8—H8C	109.5	C7—C10—H10B	109.5
O3—C7—C9	110.52 (16)	H10A—C10—H10B	109.5
O3—C7—C10	109.00 (17)	C7—C10—H10C	109.5
C9—C7—C10	112.76 (19)	H10A—C10—H10C	109.5
O3—C7—C8	101.95 (15)	H10B—C10—H10C	109.5
C9—C7—C8	110.19 (18)	C1—N2—H2C	119.9 (15)
C10—C7—C8	111.90 (18)	C1—N2—H2D	112.7 (15)
C6—O3—C7	121.19 (14)	H2C—N2—H2D	120 (2)
O2—C6—O3	124.82 (16)	N3—C5—C4	113.42 (14)
O2—C6—N4	123.46 (17)	N3—C5—H5A	108.9
O3—C6—N4	111.70 (15)	C4—C5—H5A	108.9
C6—N4—C3	123.10 (15)	N3—C5—H5B	108.9
C6—N4—C4	117.64 (15)	C4—C5—H5B	108.9
C3—N4—C4	115.06 (15)	H5A—C5—H5B	107.7
N4—C3—C2	110.37 (15)	N4—C4—C5	110.69 (15)
N4—C3—H3A	109.6	N4—C4—H4A	109.5
C2—C3—H3A	109.6	C5—C4—H4A	109.5
N4—C3—H3B	109.6	N4—C4—H4B	109.5
C2—C3—H3B	109.6	C5—C4—H4B	109.5
H3A—C3—H3B	108.1	H4A—C4—H4B	108.1
N3—C2—C3	111.33 (14)	C7—C9—H9A	109.5
N3—C2—H2A	109.4	C7—C9—H9B	109.5
C3—C2—H2A	109.4	H9A—C9—H9B	109.5
N3—C2—H2B	109.4	C7—C9—H9C	109.5
C3—C2—H2B	109.4	H9A—C9—H9C	109.5
H2A—C2—H2B	108	H9B—C9—H9C	109.5
C1—N3—C5	117.38 (15)	N1—O1—H1	109.5
C1—N3—C2	116.57 (15)	C1—N1—O1	109.58 (16)
C9—C7—O3—C6	60.5 (2)	C3—C2—N3—C5	−59.90 (19)
C10—C7—O3—C6	−64.0 (2)	C5—N3—C1—N1	−3.9 (2)
C8—C7—O3—C6	177.58 (17)	C2—N3—C1—N1	−135.54 (18)
C7—O3—C6—O2	−1.7 (3)	C5—N3—C1—N2	175.79 (15)
C7—O3—C6—N4	179.86 (15)	C2—N3—C1—N2	44.1 (2)
O2—C6—N4—C3	165.07 (18)	C1—N3—C5—C4	−77.5 (2)
O3—C6—N4—C3	−16.5 (2)	C2—N3—C5—C4	57.6 (2)
O2—C6—N4—C4	9.3 (3)	C6—N4—C4—C5	−154.43 (16)
O3—C6—N4—C4	−172.28 (15)	C3—N4—C4—C5	47.9 (2)
C6—N4—C3—C2	152.67 (16)	N3—C5—C4—N4	−51.3 (2)
C4—N4—C3—C2	−51.0 (2)	N2—C1—N1—O1	4.7 (3)
N4—C3—C2—N3	56.6 (2)	N3—C1—N1—O1	−175.65 (15)
C3—C2—N3—C1	75.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2D···O1	0.94 (3)	2.08 (3)	2.538 (2)	108.3 (19)
N2—H2C···O2i	0.89 (3)	2.10 (3)	2.988 (2)	173 (3)
O1—H1···N1ii	0.82	2.04	2.764 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2D⋯O1	0.94 (3)	2.08 (3)	2.538 (2)	108.3 (19)
N2—H2C⋯O2i	0.89 (3)	2.10 (3)	2.988 (2)	173 (3)
O1—H1⋯N1ii	0.82	2.04	2.764 (3)	147

Symmetry codes: (i) ; (ii) .