Ethyl 3-oxo-2-[(4-sulfamoylphen-yl)hydra-zono]butyrate.

In the title compound, C(12)H(15)N(3)O(5)S, an intra-molecular N-H⋯O hydrogen bond between the hydrazine unit and one of the carbonyl groups may influence the mol-ecular conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds, including one which is bifurcated, link the mol-ecules into a two-dimensional network.

Related literature

For background to sulfa drugs and their derivatives, see: Abbate et al. (2004 ▶); Badr (2008 ▶); Hanafy et al. (2007 ▶); n class="Chemical">Novinson et al. (1976 ▶); Supuran et al. (2003 ▶); Upadhyay et al. (2009 ▶); Zhong et al. (2007 ▶). For the synthesis of the title compound, see: Prakash & Gambhir (1964 ▶).

Experimental

Crystal data

C12H15N3O5S

M = 313.33

Monoclinic,

a = 7.490 (6) Å

b = 14.819 (12) Å

c = 12.689 (10) Å

β = 95.219 (14)°

V = 1402.6 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.940, T max = 0.951

11777 measured reflections

3274 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.222

S = 0.87

3274 reflections

200 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2008 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036927/lh2879sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036927/lh2879Isup2.hkl

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

C12H15N3O5S	F(000) = 656
Mr = 313.33	Dx = 1.484 Mg m−3
Monoclinic, P21/n	Melting point: 398 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.490 (6) Å	Cell parameters from 598 reflections
b = 14.819 (12) Å	θ = 2.5–27.5°
c = 12.689 (10) Å	µ = 0.26 mm−1
β = 95.219 (14)°	T = 293 K
V = 1402.6 (19) Å3	Rectangular, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Bruker SMART APEX diffractometer	3274 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 0.3 pixels mm-1	θmax = 28.2°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→19
Tmin = 0.940, Tmax = 0.951	l = −16→16
11777 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full with fixed elements per cycle	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.1321P)2 + 2.1941P] where P = (Fo2 + 2Fc2)/3
3274 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
C1	0.2438 (5)	0.0661 (2)	0.9456 (3)	0.0391 (8)
C2	0.2126 (5)	0.1343 (2)	1.0159 (3)	0.0429 (8)
H2	0.1983	0.1209	1.0862	0.051*
C3	0.2030 (5)	0.2223 (2)	0.9809 (3)	0.0433 (8)
H3	0.1809	0.2684	1.0278	0.052*
C4	0.2258 (5)	0.2424 (2)	0.8772 (2)	0.0372 (7)
C5	0.2609 (6)	0.1745 (2)	0.8081 (3)	0.0518 (10)
H5	0.2790	0.1883	0.7384	0.062*
C6	0.2693 (6)	0.0861 (2)	0.8420 (3)	0.0536 (10)
H6	0.2920	0.0401	0.7951	0.064*
C7	0.2498 (5)	−0.1296 (2)	1.1080 (3)	0.0400 (8)
C8	0.2482 (5)	−0.1381 (2)	1.2239 (3)	0.0451 (9)
C9	0.2452 (7)	−0.0539 (3)	1.2876 (3)	0.0659 (13)
H9A	0.2411	−0.0691	1.3609	0.099*
H9B	0.1412	−0.0190	1.2639	0.099*
H9C	0.3513	−0.0193	1.2791	0.099*
C10	0.2599 (5)	−0.2072 (2)	1.0344 (3)	0.0466 (9)
C11	0.2122 (7)	−0.3643 (3)	0.9952 (4)	0.0624 (12)
H11A	0.1498	−0.4147	1.0240	0.075*
H11B	0.1458	−0.3458	0.9296	0.075*
C12	0.3910 (8)	−0.3914 (3)	0.9752 (5)	0.0868 (17)
H12A	0.4491	−0.3427	0.9419	0.130*
H12B	0.3847	−0.4431	0.9294	0.130*
H12C	0.4583	−0.4064	1.0409	0.130*
H3A	0.042 (6)	0.330 (3)	0.688 (4)	0.055 (13)*
H3B	−0.064 (6)	0.334 (3)	0.769 (4)	0.049 (14)*
N1	0.2500 (4)	−0.02524 (19)	0.9754 (2)	0.0469 (8)
H1	0.2567	−0.0667	0.9286	0.056*
N2	0.2454 (4)	−0.0464 (2)	1.0745 (2)	0.0417 (7)
N3	0.0211 (6)	0.3532 (2)	0.7471 (3)	0.0481 (8)
O1	0.1619 (4)	0.40903 (16)	0.9163 (2)	0.0565 (8)
O2	0.3416 (4)	0.37652 (19)	0.7692 (2)	0.0581 (8)
O4	0.2924 (5)	−0.19684 (19)	0.9443 (2)	0.0711 (10)
O5	0.2233 (5)	−0.28696 (17)	1.0729 (2)	0.0620 (8)
O6	0.2547 (5)	−0.21135 (18)	1.2667 (2)	0.0703 (9)
S1	0.19753 (14)	0.35341 (5)	0.82925 (7)	0.0425 (3)

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.0279 (16)	0.0399 (17)	0.0027 (14)	0.0025 (15)	0.0052 (13)
C2	0.062 (2)	0.0381 (18)	0.0278 (15)	0.0020 (16)	0.0020 (15)	0.0040 (13)
C3	0.064 (2)	0.0317 (17)	0.0343 (16)	0.0012 (15)	0.0031 (15)	−0.0030 (13)
C4	0.052 (2)	0.0285 (15)	0.0305 (15)	−0.0009 (14)	0.0022 (14)	0.0018 (12)
C5	0.090 (3)	0.0346 (18)	0.0333 (17)	0.0059 (19)	0.0183 (18)	0.0050 (14)
C6	0.094 (3)	0.0294 (17)	0.0392 (19)	0.0098 (19)	0.0148 (19)	0.0008 (14)
C7	0.050 (2)	0.0328 (17)	0.0372 (17)	−0.0006 (14)	0.0043 (15)	0.0048 (13)
C8	0.055 (2)	0.0417 (19)	0.0383 (18)	−0.0101 (16)	0.0017 (16)	0.0054 (15)
C9	0.107 (4)	0.049 (2)	0.043 (2)	−0.015 (2)	0.010 (2)	−0.0031 (18)
C10	0.064 (2)	0.0351 (18)	0.0416 (19)	0.0099 (16)	0.0103 (17)	0.0076 (15)
C11	0.087 (3)	0.043 (2)	0.059 (3)	−0.006 (2)	0.021 (2)	0.0042 (18)
C12	0.091 (4)	0.053 (3)	0.112 (5)	0.004 (3)	−0.009 (3)	0.000 (3)
N1	0.073 (2)	0.0307 (15)	0.0374 (15)	0.0042 (14)	0.0051 (14)	0.0063 (12)
N2	0.0537 (18)	0.0352 (15)	0.0361 (14)	−0.0017 (13)	0.0032 (12)	0.0083 (12)
N3	0.065 (2)	0.0373 (17)	0.0423 (18)	0.0005 (16)	0.0055 (16)	0.0075 (14)
O1	0.088 (2)	0.0294 (12)	0.0521 (15)	−0.0011 (13)	0.0082 (14)	−0.0060 (11)
O2	0.0708 (19)	0.0462 (15)	0.0591 (17)	−0.0080 (13)	0.0152 (14)	0.0121 (13)
O4	0.134 (3)	0.0380 (15)	0.0465 (15)	0.0136 (16)	0.0350 (18)	0.0071 (12)
O5	0.113 (2)	0.0307 (13)	0.0460 (15)	0.0019 (14)	0.0270 (15)	0.0046 (11)
O6	0.129 (3)	0.0427 (16)	0.0384 (14)	−0.0148 (17)	0.0026 (16)	0.0117 (12)
S1	0.0625 (6)	0.0252 (4)	0.0400 (5)	−0.0026 (4)	0.0053 (4)	0.0042 (3)

C1—C6	1.379 (5)	C9—H9B	0.9600
C1—C2	1.382 (5)	C9—H9C	0.9600
C1—N1	1.404 (4)	C10—O4	1.200 (4)
C2—C3	1.378 (5)	C10—O5	1.317 (4)
C2—H2	0.9300	C11—C12	1.443 (7)
C3—C4	1.375 (5)	C11—O5	1.509 (5)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.376 (5)	C11—H11B	0.9700
C4—S1	1.760 (3)	C12—H12A	0.9600
C5—C6	1.379 (5)	C12—H12B	0.9600
C5—H5	0.9300	C12—H12C	0.9600
C6—H6	0.9300	N1—N2	1.300 (4)
C7—N2	1.304 (4)	N1—H1	0.8600
C7—C8	1.477 (5)	N3—S1	1.607 (4)
C7—C10	1.488 (5)	N3—H3A	0.85 (5)
C8—O6	1.213 (4)	N3—H3B	0.77 (4)
C8—C9	1.488 (5)	O1—S1	1.423 (3)
C9—H9A	0.9600	O2—S1	1.419 (3)
C6—C1—C2	120.3 (3)	O4—C10—O5	122.4 (4)
C6—C1—N1	117.4 (3)	O4—C10—C7	121.7 (3)
C2—C1—N1	122.3 (3)	O5—C10—C7	115.9 (3)
C3—C2—C1	119.5 (3)	C12—C11—O5	109.3 (4)
C3—C2—H2	120.3	C12—C11—H11A	109.8
C1—C2—H2	120.3	O5—C11—H11A	109.8
C4—C3—C2	120.4 (3)	C12—C11—H11B	109.8
C4—C3—H3	119.8	O5—C11—H11B	109.8
C2—C3—H3	119.8	H11A—C11—H11B	108.3
C3—C4—C5	120.0 (3)	C11—C12—H12A	109.5
C3—C4—S1	120.8 (3)	C11—C12—H12B	109.5
C5—C4—S1	119.1 (3)	H12A—C12—H12B	109.5
C4—C5—C6	120.1 (3)	C11—C12—H12C	109.5
C4—C5—H5	119.9	H12A—C12—H12C	109.5
C6—C5—H5	119.9	H12B—C12—H12C	109.5
C1—C6—C5	119.7 (3)	N2—N1—C1	119.3 (3)
C1—C6—H6	120.1	N2—N1—H1	120.3
C5—C6—H6	120.1	C1—N1—H1	120.3
N2—C7—C8	113.7 (3)	N1—N2—C7	122.7 (3)
N2—C7—C10	121.9 (3)	S1—N3—H3A	111 (3)
C8—C7—C10	124.4 (3)	S1—N3—H3B	115 (3)
O6—C8—C7	121.2 (3)	H3A—N3—H3B	113 (5)
O6—C8—C9	120.6 (3)	C10—O5—C11	116.1 (3)
C7—C8—C9	118.1 (3)	O2—S1—O1	118.86 (18)
C8—C9—H9A	109.5	O2—S1—N3	105.8 (2)
C8—C9—H9B	109.5	O1—S1—N3	107.7 (2)
H9A—C9—H9B	109.5	O2—S1—C4	109.76 (17)
C8—C9—H9C	109.5	O1—S1—C4	107.32 (16)
H9A—C9—H9C	109.5	N3—S1—C4	106.76 (17)
H9B—C9—H9C	109.5
C6—C1—C2—C3	1.5 (6)	N2—C7—C10—O5	−165.3 (4)
N1—C1—C2—C3	−178.1 (3)	C8—C7—C10—O5	16.2 (6)
C1—C2—C3—C4	−0.6 (6)	C6—C1—N1—N2	172.9 (4)
C2—C3—C4—C5	−0.9 (6)	C2—C1—N1—N2	−7.5 (5)
C2—C3—C4—S1	175.3 (3)	C1—N1—N2—C7	179.7 (3)
C3—C4—C5—C6	1.5 (6)	C8—C7—N2—N1	178.4 (3)
S1—C4—C5—C6	−174.8 (3)	C10—C7—N2—N1	−0.2 (6)
C2—C1—C6—C5	−1.0 (6)	O4—C10—O5—C11	−4.0 (6)
N1—C1—C6—C5	178.7 (4)	C7—C10—O5—C11	173.1 (3)
C4—C5—C6—C1	−0.5 (7)	C12—C11—O5—C10	77.1 (5)
N2—C7—C8—O6	−178.8 (4)	C3—C4—S1—O2	133.9 (3)
C10—C7—C8—O6	−0.3 (6)	C5—C4—S1—O2	−49.9 (4)
N2—C7—C8—C9	−1.0 (5)	C3—C4—S1—O1	3.4 (4)
C10—C7—C8—C9	177.5 (4)	C5—C4—S1—O1	179.6 (3)
N2—C7—C10—O4	11.8 (6)	C3—C4—S1—N3	−111.9 (3)
C8—C7—C10—O4	−166.7 (4)	C5—C4—S1—N3	64.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.95	2.597 (5)	131
N3—H3B···O6i	0.77 (5)	2.33 (4)	2.941 (6)	137 (4)
N3—H3B···O5i	0.77 (5)	2.52 (5)	3.208 (6)	149 (5)
N3—H3A···O4ii	0.85 (5)	2.21 (5)	3.003 (6)	154 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	1.95	2.597 (5)	131
N3—H3B⋯O6i	0.77 (5)	2.33 (4)	2.941 (6)	137 (4)
N3—H3B⋯O5i	0.77 (5)	2.52 (5)	3.208 (6)	149 (5)
N3—H3A⋯O4ii	0.85 (5)	2.21 (5)	3.003 (6)	154 (4)

Symmetry codes: (i) ; (ii) .