4-[(3-Formyl-4-hydroxy-phen-yl)diazen-yl]-N-(pyrimidin-2-yl)benzene-sulfonamide.

The title mol-ecule, C(17)H(13)N(5)O(4)S, has a trans configuration with respect to the diazenyl (azo) group. The pyrimidine ring and the terminal benzene ring are inclined at angles of 89.38 (4) and 1.6 (6)°, respectively, with respect to the central benzene ring. The conformation of the mol-ecule is in part stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal structure, mol-ecules related through inversion centers form hydrogen-bonded dimers involving the sulfon-amide N-H group and the N atom of the pyrimidine ring.

Related literature

For related literature, see: Gaber et al. (2008 ▶ and references therein); Kakoti et al. (1993 ▶); La Roche & Co (1967a,b); Misra et al. (1998 ▶); Mubarak et al. (2007 ▶); Nagaraja et al. (2002 ▶); Santra & Lahiri (1997 ▶); Vaichulis (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13N5O4S

M = 383.39

Monoclinic,

a = 18.579 (2) Å

b = 5.7731 (7) Å

c = 17.372 (2) Å

β = 115.99 (1)°

V = 1674.73 Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.977

17304 measured reflections

3560 independent reflections

3277 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.05

3560 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: KENX (Sakai, 2004 ▶); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001 ▶), KENX and ORTEPII (Johnson, 1976 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024239/lh2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024239/lh2668Isup2.hkl

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

C17H13N5O4S	F000 = 792
Mr = 383.39	? # Insert any comments here.
Monoclinic, P21/c	Dx = 1.521 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 18.579 (2) Å	Cell parameters from 9950 reflections
b = 5.7731 (7) Å	θ = 2.4–28.3º
c = 17.372 (2) Å	µ = 0.23 mm−1
β = 115.99 (1)º	T = 100 (2) K
V = 1674.73 Å3	Block, dark orange
Z = 4	0.30 × 0.20 × 0.10 mm

Bruker SMART APEX CCD diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	3277 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 100(2) K	θmax = 26.7º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.934, Tmax = 0.977	k = −7→7
17304 measured reflections	l = −21→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.9337P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.42 e Å−3
3560 reflections	Δρmin = −0.37 e Å−3
245 parameters	Extinction correction: none
Secondary atom site location: difference Fourier map

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)13.7836 (0.0041) x + 2.4391 (0.0022) y - 13.7785 (0.0036) z = 4.2437 (0.0052)* 0.0258 (0.0010) O1 * -0.0309 (0.0010) O2 * 0.0133 (0.0012) C1 * -0.0188 (0.0013) C2 * -0.0067 (0.0012) C3 * 0.0010 (0.0012) C4 * 0.0430 (0.0013) C5 * 0.0139 (0.0012) C6 * -0.0207 (0.0013) C7 * -0.0198 (0.0009) N1 - 0.1255 (0.0017) N2 - 0.2396 (0.0024) C9 - 0.2576 (0.0024) C10 - 0.2407 (0.0024) C11 - 0.2117 (0.0022) C12 - 0.1607 (0.0019) C13Rms deviation of fitted atoms = 0.022513.5655 (0.0045) x + 2.3850 (0.0032) y - 14.0573 (0.0043) z = 3.6030 (0.0035)Angle to previous plane (with approximate e.s.d.) = 1.60 (0.06)* 0.0132 (0.0011) N2 * -0.0021 (0.0008) C9 * -0.0021 (0.0012) C10 * -0.0053 (0.0012) C11 * -0.0149 (0.0012) C12 * 0.0178 (0.0013) C13 * -0.0066 (0.0004) O1 - 0.0637 (0.0021) O2 0.0152 (0.0018) C1 0.0043 (0.0016) C2 0.0555 (0.0016) C3 0.0836 (0.0016) C4 0.1066 (0.0021) C5 0.0390 (0.0023) C6 - 0.0162 (0.0020) C7 0.1025 (0.0013) N1Rms deviation of fitted atoms = 0.01062.8895 (0.0099) x + 3.8287 (0.0026) y + 10.2469 (0.0065) z = 10.3651 (0.0036)Angle to previous plane (with approximate e.s.d.) = 89.38 (0.04)* -0.0192 (0.0009) N3 * 0.0179 (0.0011) N4 * 0.0136 (0.0010) N5 * 0.0038 (0.0012) C14 * -0.0009 (0.0012) C15 * -0.0197 (0.0013) C16 * 0.0045 (0.0011) C17Rms deviation of fitted atoms = 0.0136

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
S1	0.67904 (2)	0.77281 (6)	0.52372 (2)	0.02455 (11)
O1	1.32533 (7)	0.9734 (2)	1.18827 (7)	0.0366 (3)
N5	0.49729 (7)	0.7981 (2)	0.57442 (7)	0.0246 (3)
O4	0.67616 (6)	0.9243 (2)	0.45700 (6)	0.0301 (2)
O3	0.68746 (6)	0.52911 (19)	0.51537 (7)	0.0297 (2)
C17	0.46694 (9)	0.6915 (3)	0.62192 (9)	0.0289 (3)
H13	0.4169	0.7418	0.6183	0.035*
N2	0.94619 (7)	1.1123 (2)	0.84456 (8)	0.0282 (3)
N3	0.59631 (7)	0.8311 (2)	0.53095 (8)	0.0280 (3)
H10	0.5668	0.9446	0.4987	0.034*
N1	1.00856 (7)	0.9914 (2)	0.87789 (8)	0.0280 (3)
O2	1.24471 (7)	1.3545 (2)	1.17919 (7)	0.0332 (3)
H1	1.2835	1.2624	1.2013	0.050*
C15	0.57921 (10)	0.4485 (3)	0.68056 (10)	0.0357 (4)
H11	0.6079	0.3262	0.7181	0.043*
C16	0.50602 (9)	0.5108 (3)	0.67607 (10)	0.0338 (3)
H12	0.4835	0.4332	0.7086	0.041*
C1	1.26947 (9)	0.9081 (3)	1.12173 (10)	0.0310 (3)
H2	1.2736	0.7616	1.0991	0.037*
C5	1.06241 (9)	1.3131 (3)	0.98413 (10)	0.0297 (3)
H4	1.0171	1.4067	0.9518	0.036*
C6	1.12111 (9)	1.3967 (3)	1.05977 (10)	0.0299 (3)
H5	1.1155	1.5451	1.0802	0.036*
C12	0.81694 (9)	1.1545 (3)	0.72898 (9)	0.0288 (3)
H9	0.8145	1.2998	0.7534	0.035*
C11	0.75308 (9)	1.0818 (3)	0.65434 (9)	0.0286 (3)
H8	0.7074	1.1777	0.6262	0.034*
C8	0.88818 (9)	0.7981 (3)	0.73479 (9)	0.0279 (3)
H6	0.9343	0.7034	0.7621	0.034*
C7	1.18899 (9)	1.2628 (3)	1.10648 (9)	0.0269 (3)
C4	1.06845 (9)	1.0915 (3)	0.95400 (9)	0.0265 (3)
C3	1.13632 (9)	0.9607 (3)	0.99930 (9)	0.0266 (3)
H3	1.1417	0.8129	0.9783	0.032*
C9	0.82375 (9)	0.7222 (3)	0.66129 (9)	0.0264 (3)
H7	0.8249	0.5737	0.6383	0.032*
C13	0.88463 (9)	1.0158 (3)	0.76846 (9)	0.0266 (3)
C2	1.19719 (9)	1.0441 (3)	1.07584 (9)	0.0266 (3)
N4	0.61192 (8)	0.5519 (2)	0.63453 (8)	0.0328 (3)
C14	0.56803 (8)	0.7196 (2)	0.58287 (9)	0.0246 (3)
C10	0.75726 (8)	0.8652 (3)	0.62140 (9)	0.0242 (3)

	U11	U22	U33	U12	U13	U23
S1	0.02184 (18)	0.0280 (2)	0.02274 (19)	0.00350 (13)	0.00873 (14)	0.00169 (13)
O1	0.0312 (6)	0.0394 (6)	0.0338 (6)	0.0059 (5)	0.0091 (5)	0.0096 (5)
N5	0.0208 (6)	0.0265 (6)	0.0224 (6)	0.0000 (5)	0.0057 (5)	0.0021 (5)
O4	0.0290 (5)	0.0365 (6)	0.0256 (5)	0.0041 (4)	0.0127 (4)	0.0044 (4)
O3	0.0266 (5)	0.0294 (6)	0.0289 (5)	0.0017 (4)	0.0083 (4)	−0.0033 (4)
C17	0.0238 (7)	0.0335 (8)	0.0269 (7)	−0.0013 (6)	0.0090 (6)	0.0028 (6)
N2	0.0279 (6)	0.0288 (6)	0.0271 (6)	0.0006 (5)	0.0114 (5)	−0.0006 (5)
N3	0.0231 (6)	0.0318 (7)	0.0284 (6)	0.0076 (5)	0.0107 (5)	0.0102 (5)
N1	0.0277 (6)	0.0293 (6)	0.0275 (6)	0.0005 (5)	0.0127 (5)	0.0003 (5)
O2	0.0292 (6)	0.0361 (6)	0.0280 (5)	0.0013 (5)	0.0066 (4)	−0.0008 (5)
C15	0.0342 (8)	0.0351 (8)	0.0319 (8)	0.0044 (7)	0.0091 (6)	0.0127 (7)
C16	0.0312 (8)	0.0368 (8)	0.0310 (7)	−0.0031 (6)	0.0115 (6)	0.0091 (6)
C1	0.0311 (7)	0.0297 (8)	0.0333 (8)	0.0039 (6)	0.0150 (6)	0.0073 (6)
C5	0.0255 (7)	0.0300 (8)	0.0311 (8)	0.0052 (6)	0.0100 (6)	0.0016 (6)
C6	0.0301 (7)	0.0261 (7)	0.0323 (8)	0.0024 (6)	0.0127 (6)	−0.0017 (6)
C12	0.0341 (8)	0.0228 (7)	0.0294 (7)	0.0023 (6)	0.0139 (6)	−0.0011 (6)
C11	0.0295 (7)	0.0258 (7)	0.0289 (7)	0.0065 (6)	0.0114 (6)	0.0034 (6)
C8	0.0245 (7)	0.0319 (8)	0.0267 (7)	0.0056 (6)	0.0105 (6)	0.0004 (6)
C7	0.0256 (7)	0.0298 (7)	0.0257 (7)	−0.0016 (6)	0.0116 (6)	0.0022 (6)
C4	0.0264 (7)	0.0287 (7)	0.0256 (7)	−0.0005 (6)	0.0126 (6)	0.0003 (6)
C3	0.0297 (7)	0.0240 (7)	0.0296 (7)	0.0006 (6)	0.0162 (6)	0.0016 (6)
C9	0.0272 (7)	0.0264 (7)	0.0266 (7)	0.0044 (6)	0.0129 (6)	−0.0010 (6)
C13	0.0272 (7)	0.0289 (7)	0.0243 (7)	−0.0008 (6)	0.0118 (6)	0.0002 (6)
C2	0.0265 (7)	0.0272 (7)	0.0280 (7)	0.0011 (6)	0.0138 (6)	0.0057 (6)
N4	0.0275 (6)	0.0359 (7)	0.0309 (7)	0.0074 (5)	0.0091 (5)	0.0113 (6)
C14	0.0220 (6)	0.0261 (7)	0.0220 (6)	0.0002 (5)	0.0064 (5)	0.0011 (5)
C10	0.0236 (7)	0.0276 (7)	0.0214 (6)	0.0013 (5)	0.0099 (5)	0.0012 (5)

S1—O3	1.4299 (11)	C11—C10	1.391 (2)
S1—O4	1.4343 (11)	C8—C9	1.384 (2)
S1—N3	1.6311 (12)	C8—C13	1.400 (2)
S1—C10	1.7647 (15)	C7—C2	1.404 (2)
O1—C1	1.226 (2)	C4—C3	1.382 (2)
N5—C14	1.3362 (19)	C3—C2	1.400 (2)
N5—C17	1.3362 (19)	C9—C10	1.392 (2)
C17—C16	1.379 (2)	C1—O3i	2.9106 (19)
N2—N1	1.2558 (18)	C5—H4	0.9500
N2—C13	1.4285 (19)	N3—H10	0.8800
N3—C14	1.3857 (19)	C1—H2	0.9500
N4—C14	1.3289 (19)	C6—H5	0.9500
N1—C4	1.4250 (19)	C8—H6	0.9500
O2—C7	1.3420 (18)	C15—H11	0.9500
C15—N4	1.338 (2)	C16—H12	0.9500
C15—C16	1.375 (2)	C12—H9	0.9500
C1—C2	1.455 (2)	O2—H1	0.8400
C5—C6	1.376 (2)	C11—H8	0.9500
C5—C4	1.405 (2)	C3—H3	0.9500
C6—C7	1.396 (2)	C17—H13	0.9500
C12—C11	1.384 (2)	C9—H7	0.9500
C12—C13	1.392 (2)
O3—S1—O4	119.02 (7)	C13—C12—H9	119.8
O3—S1—N3	111.08 (7)	C12—C11—C10	118.57 (13)
O4—S1—N3	103.51 (6)	C12—C11—H8	120.7
O3—S1—C10	108.31 (7)	C10—C11—H8	120.7
O4—S1—C10	108.42 (7)	C9—C8—C13	119.32 (13)
N3—S1—C10	105.68 (7)	C9—C8—H6	120.3
C14—N5—C17	115.89 (13)	C13—C8—H6	120.3
N5—C17—C16	122.09 (14)	O2—C7—C6	117.16 (14)
N5—C17—H13	119.0	O2—C7—C2	122.97 (13)
C16—C17—H13	119.0	C6—C7—C2	119.87 (14)
N1—N2—C13	114.37 (13)	C3—C4—C5	119.16 (14)
C14—N3—S1	126.38 (10)	C3—C4—N1	116.95 (13)
C14—N3—H10	116.8	C5—C4—N1	123.89 (13)
S1—N3—H10	116.8	C4—C3—C2	120.56 (14)
N2—N1—C4	112.94 (13)	C4—C3—H3	119.7
C7—O2—H1	109.5	C2—C3—H3	119.7
N4—C15—C16	123.09 (15)	C8—C9—C10	119.44 (14)
N4—C15—H11	118.5	C8—C9—H7	120.3
C16—C15—H11	118.5	C10—C9—H7	120.3
C15—C16—C17	116.64 (14)	C12—C13—C8	120.55 (14)
C15—C16—H12	121.7	C12—C13—N2	114.57 (13)
C17—C16—H12	121.7	C8—C13—N2	124.86 (13)
O1—C1—C2	123.15 (15)	C3—C2—C7	119.50 (13)
O1—C1—H2	118.4	C3—C2—C1	120.14 (14)
C2—C1—H2	118.4	C7—C2—C1	120.34 (14)
C6—C5—C4	121.07 (14)	C14—N4—C15	115.06 (13)
C6—C5—H4	119.5	N4—C14—N5	127.19 (14)
C4—C5—H4	119.5	N4—C14—N3	118.86 (13)
C5—C6—C7	119.78 (14)	N5—C14—N3	113.95 (12)
C5—C6—H5	120.1	C11—C10—C9	121.71 (13)
C7—C6—H5	120.1	C11—C10—S1	119.74 (11)
C11—C12—C13	120.37 (14)	C9—C10—S1	118.47 (11)
C11—C12—H9	119.8
C14—N5—C17—C16	−0.3 (2)	C4—C3—C2—C1	−178.17 (13)
O3—S1—N3—C14	46.71 (15)	O2—C7—C2—C3	−179.94 (13)
O4—S1—N3—C14	175.57 (13)	C6—C7—C2—C3	−1.2 (2)
C10—S1—N3—C14	−70.55 (14)	O2—C7—C2—C1	−1.9 (2)
C13—N2—N1—C4	−179.50 (12)	C6—C7—C2—C1	176.90 (14)
N4—C15—C16—C17	−1.1 (3)	O1—C1—C2—C3	178.82 (14)
N5—C17—C16—C15	1.6 (2)	O1—C1—C2—C7	0.8 (2)
C4—C5—C6—C7	1.8 (2)	C16—C15—N4—C14	−0.6 (2)
C13—C12—C11—C10	1.9 (2)	C15—N4—C14—N5	2.2 (2)
C5—C6—C7—O2	179.17 (13)	C15—N4—C14—N3	−178.08 (14)
C5—C6—C7—C2	0.3 (2)	C17—N5—C14—N4	−1.7 (2)
C6—C5—C4—C3	−3.0 (2)	C17—N5—C14—N3	178.51 (13)
C6—C5—C4—N1	177.69 (14)	S1—N3—C14—N4	2.0 (2)
N2—N1—C4—C3	174.33 (13)	S1—N3—C14—N5	−178.19 (11)
N2—N1—C4—C5	−6.4 (2)	C12—C11—C10—C9	−0.3 (2)
C5—C4—C3—C2	2.2 (2)	C12—C11—C10—S1	−177.03 (11)
N1—C4—C3—C2	−178.51 (12)	C8—C9—C10—C11	−1.2 (2)
C13—C8—C9—C10	1.1 (2)	C8—C9—C10—S1	175.57 (11)
C11—C12—C13—C8	−2.0 (2)	O3—S1—C10—C11	−165.58 (11)
C11—C12—C13—N2	179.57 (13)	O4—S1—C10—C11	63.96 (13)
C9—C8—C13—C12	0.4 (2)	N3—S1—C10—C11	−46.48 (13)
C9—C8—C13—N2	178.74 (14)	O3—S1—C10—C9	17.59 (14)
N1—N2—C13—C12	−177.01 (13)	O4—S1—C10—C9	−112.87 (12)
N1—N2—C13—C8	4.6 (2)	N3—S1—C10—C9	136.69 (12)
C4—C3—C2—C7	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.84	1.90	2.6269 (17)	145
N3—H10···N5i	0.88	1.98	2.8574 (17)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	0.84	1.90	2.6269 (17)	145
N3—H10⋯N5i	0.88	1.98	2.8574 (17)	179

Symmetry code: (i) .