4-[2-(1-Acetyl-2-oxopropyl-idene)-hydrazino]-N-(pyrimidin-2-yl)benzene-sulfonamide.

In the title compound, C(15)H(15)N(5)O(4)S, the dihedral angle between the pyrimidine and benzene rings is 84.56 (2)°. Intra-molecular hydrazine-carbonyl N-H⋯O and inter-molecular sulfonamide-pyridimine N-H⋯N hydrogen bonds stabilize the mol-ecular and crystal structures, respectively.

Related literature

For background to sulfa drugs and their derivatives, see: Abbate et al. (2004 ▶); Badr (2008 ▶); Gale et al. (2007 ▶); Hanafy et al. (2007 ▶); Novinson et al. (1976 ▶); Supuran et al. (2003 ▶). For the synthesis of the title compound, see: Goyal & Bhargava (1989 ▶).

Experimental

Crystal data

C15H15N5O4S

M = 361.38

Monoclinic,

a = 11.354 (3) Å

b = 5.7875 (13) Å

c = 25.974 (6) Å

β = 101.877 (4)°

V = 1670.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2005 ▶) T min = 0.947, T max = 0.957

17935 measured reflections

3999 independent reflections

3164 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.07

3999 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018765/tk2450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018765/tk2450Isup2.hkl

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

C15H15N5O4S	F(000) = 752
Mr = 361.38	Dx = 1.437 Mg m−3
Monoclinic, P21/n	Melting point: 508 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.354 (3) Å	Cell parameters from 489 reflections
b = 5.7875 (13) Å	θ = 2.5–27.5°
c = 25.974 (6) Å	µ = 0.23 mm−1
β = 101.877 (4)°	T = 293 K
V = 1670.3 (7) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Bruker SMART APEX diffractometer	3999 independent reflections
Radiation source: fine-focus sealed tube	3164 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 0.3 pixels mm-1	θmax = 28.2°, θmin = 1.6°
ω scans	h = −14→14
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.947, Tmax = 0.957	l = −33→34
17935 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.3686P] where P = (Fo2 + 2Fc2)/3
3999 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.27 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	0.63840 (13)	0.4007 (3)	0.17280 (6)	0.0382 (3)
C2	0.65017 (14)	0.2375 (3)	0.21231 (6)	0.0423 (4)
H2	0.6861	0.0958	0.2085	0.051*
C3	0.60841 (14)	0.2856 (3)	0.25745 (6)	0.0442 (4)
H3	0.6172	0.1775	0.2845	0.053*
C4	0.55332 (13)	0.4960 (3)	0.26228 (6)	0.0403 (3)
C5	0.54124 (15)	0.6595 (3)	0.22244 (7)	0.0441 (4)
H5	0.5036	0.7998	0.2258	0.053*
C6	0.58527 (14)	0.6128 (3)	0.17784 (6)	0.0435 (4)
H6	0.5793	0.7229	0.1513	0.052*
C7	0.41088 (16)	0.7698 (3)	0.35557 (7)	0.0508 (4)
C8	0.32001 (18)	0.9556 (4)	0.35144 (8)	0.0640 (5)
C9	0.2914 (2)	1.0962 (4)	0.30216 (10)	0.0776 (6)
H9A	0.2278	1.0230	0.2775	0.116*
H9B	0.3617	1.1078	0.2871	0.116*
H9C	0.2663	1.2480	0.3102	0.116*
C10	0.46123 (17)	0.6545 (4)	0.40679 (7)	0.0588 (5)
C11	0.4767 (3)	0.7965 (5)	0.45552 (9)	0.0890 (8)
H11A	0.5122	0.7037	0.4853	0.134*
H11B	0.3996	0.8519	0.4599	0.134*
H11C	0.5282	0.9255	0.4528	0.134*
C12	0.48295 (14)	0.2255 (3)	0.05575 (6)	0.0410 (3)
C13	0.31325 (16)	0.1234 (3)	−0.00211 (7)	0.0558 (5)
H13	0.2584	0.1438	−0.0337	0.067*
C14	0.29513 (18)	−0.0519 (4)	0.03058 (9)	0.0672 (5)
H14	0.2297	−0.1513	0.0218	0.081*
C15	0.37720 (18)	−0.0752 (4)	0.07679 (9)	0.0645 (5)
H15	0.3662	−0.1929	0.0997	0.077*
N1	0.58083 (12)	0.3715 (2)	0.06677 (5)	0.0448 (3)
H1	0.5816	0.4870	0.0460	0.054*
N2	0.51240 (12)	0.5382 (3)	0.30859 (5)	0.0473 (3)
H2A	0.5336	0.4483	0.3353	0.057*
N3	0.44158 (12)	0.7152 (3)	0.31136 (5)	0.0474 (3)
N4	0.40737 (12)	0.2669 (2)	0.00980 (5)	0.0447 (3)
N5	0.47232 (14)	0.0633 (3)	0.09050 (6)	0.0543 (4)
O1	0.77449 (10)	0.5273 (3)	0.10851 (5)	0.0599 (3)
O2	0.74016 (12)	0.1133 (2)	0.11958 (5)	0.0593 (3)
O3	0.49670 (15)	0.4579 (3)	0.40757 (6)	0.0857 (5)
O4	0.26722 (17)	0.9867 (4)	0.38702 (7)	0.1059 (6)
S1	0.69587 (3)	0.34360 (8)	0.116167 (15)	0.04382 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0377 (7)	0.0417 (8)	0.0330 (7)	0.0005 (6)	0.0023 (6)	−0.0020 (6)
C2	0.0458 (8)	0.0380 (8)	0.0418 (8)	0.0078 (6)	0.0060 (7)	−0.0003 (6)
C3	0.0475 (8)	0.0447 (8)	0.0393 (8)	0.0065 (7)	0.0064 (7)	0.0082 (6)
C4	0.0375 (7)	0.0457 (8)	0.0361 (7)	−0.0001 (6)	0.0037 (6)	−0.0044 (6)
C5	0.0471 (8)	0.0370 (8)	0.0473 (9)	0.0071 (7)	0.0076 (7)	−0.0012 (7)
C6	0.0494 (8)	0.0409 (8)	0.0381 (8)	0.0041 (7)	0.0043 (7)	0.0051 (6)
C7	0.0483 (8)	0.0587 (10)	0.0456 (9)	0.0016 (8)	0.0098 (7)	−0.0085 (8)
C8	0.0610 (11)	0.0676 (12)	0.0638 (12)	0.0124 (10)	0.0139 (9)	−0.0124 (10)
C9	0.0716 (13)	0.0735 (14)	0.0858 (16)	0.0217 (11)	0.0114 (12)	0.0035 (12)
C10	0.0551 (10)	0.0769 (13)	0.0471 (10)	0.0054 (9)	0.0167 (8)	−0.0013 (9)
C11	0.0990 (17)	0.118 (2)	0.0458 (11)	0.0011 (16)	0.0061 (11)	−0.0156 (12)
C12	0.0447 (8)	0.0441 (8)	0.0336 (7)	−0.0011 (7)	0.0066 (6)	−0.0013 (6)
C13	0.0510 (9)	0.0650 (11)	0.0470 (9)	−0.0096 (9)	−0.0002 (7)	−0.0036 (8)
C14	0.0586 (11)	0.0666 (12)	0.0724 (13)	−0.0220 (10)	0.0041 (9)	0.0041 (10)
C15	0.0647 (11)	0.0609 (11)	0.0665 (12)	−0.0138 (10)	0.0104 (10)	0.0163 (10)
N1	0.0479 (7)	0.0494 (8)	0.0336 (6)	−0.0079 (6)	−0.0002 (5)	0.0049 (6)
N2	0.0508 (7)	0.0542 (8)	0.0367 (7)	0.0081 (6)	0.0085 (6)	0.0001 (6)
N3	0.0422 (7)	0.0553 (8)	0.0431 (7)	0.0034 (6)	0.0052 (6)	−0.0083 (6)
N4	0.0469 (7)	0.0509 (8)	0.0343 (6)	−0.0053 (6)	0.0038 (5)	−0.0001 (6)
N5	0.0582 (8)	0.0566 (9)	0.0457 (8)	−0.0083 (7)	0.0054 (6)	0.0123 (7)
O1	0.0471 (6)	0.0832 (9)	0.0491 (7)	−0.0162 (6)	0.0089 (5)	−0.0029 (6)
O2	0.0637 (7)	0.0686 (8)	0.0433 (6)	0.0224 (7)	0.0057 (5)	−0.0072 (6)
O3	0.1122 (12)	0.0941 (11)	0.0564 (8)	0.0341 (10)	0.0303 (8)	0.0152 (8)
O4	0.1151 (12)	0.1252 (15)	0.0895 (12)	0.0543 (12)	0.0496 (10)	−0.0011 (11)
S1	0.04035 (19)	0.0554 (2)	0.03392 (18)	0.00152 (17)	0.00343 (15)	−0.00326 (16)

C1—C2	1.380 (2)	C10—C11	1.489 (3)
C1—C6	1.386 (2)	C11—H11A	0.9600
C1—S1	1.7590 (15)	C11—H11B	0.9600
C2—C3	1.381 (2)	C11—H11C	0.9600
C2—H2	0.9300	C12—N5	1.325 (2)
C3—C4	1.386 (2)	C12—N4	1.340 (2)
C3—H3	0.9300	C12—N1	1.378 (2)
C4—C5	1.388 (2)	C13—N4	1.339 (2)
C4—N2	1.397 (2)	C13—C14	1.366 (3)
C5—C6	1.380 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.366 (3)
C6—H6	0.9300	C14—H14	0.9300
C7—N3	1.306 (2)	C15—N5	1.333 (2)
C7—C8	1.478 (3)	C15—H15	0.9300
C7—C10	1.493 (3)	N1—S1	1.6396 (13)
C8—O4	1.214 (2)	N1—H1	0.8600
C8—C9	1.495 (3)	N2—N3	1.3136 (19)
C9—H9A	0.9600	N2—H2A	0.8600
C9—H9B	0.9600	O1—S1	1.4284 (13)
C9—H9C	0.9600	O2—S1	1.4210 (13)
C10—O3	1.206 (2)
C2—C1—C6	120.88 (14)	C10—C11—H11A	109.5
C2—C1—S1	119.82 (12)	C10—C11—H11B	109.5
C6—C1—S1	119.27 (12)	H11A—C11—H11B	109.5
C1—C2—C3	119.71 (15)	C10—C11—H11C	109.5
C1—C2—H2	120.1	H11A—C11—H11C	109.5
C3—C2—H2	120.1	H11B—C11—H11C	109.5
C2—C3—C4	119.62 (15)	N5—C12—N4	127.00 (15)
C2—C3—H3	120.2	N5—C12—N1	118.39 (14)
C4—C3—H3	120.2	N4—C12—N1	114.61 (14)
C3—C4—C5	120.56 (15)	N4—C13—C14	122.19 (17)
C3—C4—N2	117.87 (14)	N4—C13—H13	118.9
C5—C4—N2	121.56 (14)	C14—C13—H13	118.9
C6—C5—C4	119.70 (15)	C13—C14—C15	117.17 (18)
C6—C5—H5	120.2	C13—C14—H14	121.4
C4—C5—H5	120.2	C15—C14—H14	121.4
C5—C6—C1	119.51 (15)	N5—C15—C14	122.95 (18)
C5—C6—H6	120.2	N5—C15—H15	118.5
C1—C6—H6	120.2	C14—C15—H15	118.5
N3—C7—C8	114.89 (17)	C12—N1—S1	125.49 (11)
N3—C7—C10	123.56 (16)	C12—N1—H1	117.3
C8—C7—C10	121.55 (16)	S1—N1—H1	117.3
O4—C8—C7	119.93 (18)	N3—N2—C4	119.95 (14)
O4—C8—C9	121.11 (18)	N3—N2—H2A	120.0
C7—C8—C9	118.91 (18)	C4—N2—H2A	120.0
C8—C9—H9A	109.5	C7—N3—N2	120.95 (15)
C8—C9—H9B	109.5	C13—N4—C12	115.42 (15)
H9A—C9—H9B	109.5	C12—N5—C15	115.25 (16)
C8—C9—H9C	109.5	O2—S1—O1	118.93 (9)
H9A—C9—H9C	109.5	O2—S1—N1	110.86 (6)
H9B—C9—H9C	109.5	O1—S1—N1	103.75 (6)
O3—C10—C11	121.73 (19)	O2—S1—C1	108.15 (6)
O3—C10—C7	120.14 (16)	O1—S1—C1	109.07 (6)
C11—C10—C7	117.9 (2)	N1—S1—C1	105.24 (7)
C6—C1—C2—C3	0.1 (2)	N4—C12—N1—S1	−172.23 (12)
S1—C1—C2—C3	177.95 (12)	C3—C4—N2—N3	−168.07 (14)
C1—C2—C3—C4	1.0 (2)	C5—C4—N2—N3	12.8 (2)
C2—C3—C4—C5	−0.8 (2)	C8—C7—N3—N2	−173.28 (15)
C2—C3—C4—N2	−179.93 (14)	C10—C7—N3—N2	6.1 (3)
C3—C4—C5—C6	−0.5 (2)	C4—N2—N3—C7	−173.92 (15)
N2—C4—C5—C6	178.57 (14)	C14—C13—N4—C12	0.5 (3)
C4—C5—C6—C1	1.6 (2)	N5—C12—N4—C13	−1.8 (3)
C2—C1—C6—C5	−1.4 (2)	N1—C12—N4—C13	178.52 (15)
S1—C1—C6—C5	−179.29 (12)	N4—C12—N5—C15	1.9 (3)
N3—C7—C8—O4	164.74 (17)	N1—C12—N5—C15	−178.47 (16)
C10—C7—C8—O4	−14.6 (3)	C14—C15—N5—C12	−0.6 (3)
N3—C7—C8—C9	−12.8 (3)	C12—N1—S1—O2	48.04 (14)
C10—C7—C8—C9	167.8 (2)	C12—N1—S1—O1	176.80 (12)
N3—C7—C10—O3	−27.4 (3)	C12—N1—S1—C1	−68.66 (15)
C8—C7—C10—O3	151.92 (17)	C2—C1—S1—O2	4.63 (13)
N3—C7—C10—C11	146.9 (2)	C6—C1—S1—O2	−177.48 (11)
C8—C7—C10—C11	−33.8 (3)	C2—C1—S1—O1	−126.05 (12)
N4—C13—C14—C15	0.5 (3)	C6—C1—S1—O1	51.84 (13)
C13—C14—C15—N5	−0.4 (3)	C2—C1—S1—N1	123.16 (13)
N5—C12—N1—S1	8.0 (2)	C6—C1—S1—N1	−58.95 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	2.01	2.654 (2)	131
C15—H15···O4i	0.93	2.46	3.262 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	2.01	2.654 (2)	131
C15—H15⋯O4i	0.93	2.46	3.262 (3)	144

Symmetry code: (i) .