6-Chloro-9-(2-nitro-phenyl-sulfon-yl)-9H-purine.

The title compound, C(11)H(6)ClN(5)O(4)S, crystallized with two independent mol-ecules in the asymmetric unit. The benzene ring makes dihedral angles of 66.46 (8) and 85.77 (9)° with the mean plane of the purine ring in the two mol-ecules. In the crystal, inter-molecular π-π stacking inter-actions [centroid-centroid distance = 3.8968 (12) Å], C-Cl⋯π inter-actions [Cl⋯centroid = 3.2505 (10) Å, C-Cl⋯centroid = 161.56 (18)°] and non-classical C-H⋯O and C-H⋯N hydrogen bonds link the molecules.

Related literature

For general background to the chemistry, biological activity and applications of purine derivatives, see: Scozzafava et al. (2001 ▶); Bakkestuen et al. (2005 ▶).

Experimental

Crystal data

C11H6ClN5O4S

M = 339.72

Triclinic,

a = 10.0055 (3) Å

b = 10.6931 (5) Å

c = 12.5378 (5) Å

α = 93.692 (3)°

β = 97.136 (3)°

γ = 93.995 (3)°

V = 1324.16 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.42 × 0.40 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.992, T max = 1.0

10984 measured reflections

5403 independent reflections

4389 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.02

5403 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003102/su2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003102/su2246Isup2.hkl

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

C11H6ClN5O4S	Z = 4
Mr = 339.72	F(000) = 688
Triclinic, P1	Dx = 1.704 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 10.0055 (3) Å	Cell parameters from 5646 reflections
b = 10.6931 (5) Å	θ = 3.1–29.1°
c = 12.5378 (5) Å	µ = 0.47 mm−1
α = 93.692 (3)°	T = 293 K
β = 97.136 (3)°	Block, colourless
γ = 93.995 (3)°	0.42 × 0.40 × 0.35 mm
V = 1324.16 (9) Å3

Oxford Diffraction Xcalibur Eos diffractometer	5403 independent reflections
Radiation source: fine-focus sealed tube	4389 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.992, Tmax = 1.0	l = −15→12
10984 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4744P] where P = (Fo2 + 2Fc2)/3
5403 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	−0.28373 (6)	1.01998 (7)	0.86805 (5)	0.05386 (18)
Cl2	−0.10359 (6)	0.30928 (6)	0.45966 (6)	0.05239 (17)
S1	0.31769 (5)	1.10135 (5)	0.71476 (4)	0.02990 (13)
S2	0.29292 (5)	0.60128 (5)	0.16093 (4)	0.03061 (13)
O1	0.33387 (14)	1.21495 (14)	0.66297 (12)	0.0373 (3)
O2	0.39441 (14)	1.08250 (15)	0.81453 (11)	0.0403 (4)
O3	0.11604 (15)	1.08355 (17)	0.49868 (14)	0.0495 (4)
O4	0.25354 (19)	1.11017 (18)	0.38100 (14)	0.0578 (5)
O5	0.22219 (15)	0.63512 (15)	0.06322 (11)	0.0405 (4)
O6	0.37133 (15)	0.69221 (15)	0.23407 (12)	0.0446 (4)
O7	0.13521 (15)	0.38259 (17)	0.02911 (13)	0.0468 (4)
O8	0.2366 (2)	0.3163 (2)	−0.10209 (14)	0.0737 (6)
N2	−0.0813 (2)	0.8795 (2)	0.90380 (17)	0.0505 (5)
N4	0.13616 (18)	0.90598 (18)	0.84106 (15)	0.0419 (5)
N7	−0.05280 (17)	1.15618 (18)	0.74289 (14)	0.0375 (4)
N9	0.15488 (16)	1.08978 (16)	0.73571 (13)	0.0308 (4)
N16	0.21920 (18)	1.06359 (17)	0.46067 (14)	0.0369 (4)
N18	0.15591 (18)	0.36990 (18)	0.50525 (15)	0.0402 (4)
N20	0.30089 (16)	0.47424 (17)	0.39320 (13)	0.0335 (4)
N23	−0.03515 (17)	0.4610 (2)	0.25421 (15)	0.0409 (5)
N25	0.17329 (15)	0.53615 (17)	0.22797 (13)	0.0303 (4)
N32	0.23641 (18)	0.35675 (18)	−0.00913 (14)	0.0387 (4)
C1	−0.1216 (2)	0.9794 (2)	0.85674 (18)	0.0391 (5)
C3	0.0440 (2)	0.8481 (2)	0.8933 (2)	0.0517 (6)
H3	0.0702	0.7769	0.9267	0.062*
C5	0.0901 (2)	1.0062 (2)	0.79701 (16)	0.0315 (4)
C6	−0.0380 (2)	1.0496 (2)	0.79999 (16)	0.0331 (5)
C8	0.0617 (2)	1.1767 (2)	0.70684 (17)	0.0358 (5)
H8	0.0802	1.2434	0.6654	0.043*
C10	0.33847 (18)	0.97337 (19)	0.62325 (15)	0.0287 (4)
C11	0.30456 (19)	0.9715 (2)	0.51123 (16)	0.0310 (4)
C12	0.3430 (2)	0.8782 (2)	0.44359 (17)	0.0372 (5)
H12	0.3214	0.8790	0.3693	0.045*
C13	0.4141 (2)	0.7834 (2)	0.48677 (19)	0.0406 (5)
H13	0.4398	0.7196	0.4414	0.049*
C14	0.4473 (2)	0.7827 (2)	0.59658 (19)	0.0413 (5)
H14	0.4940	0.7177	0.6251	0.050*
C15	0.4114 (2)	0.8783 (2)	0.66493 (18)	0.0361 (5)
H15	0.4364	0.8785	0.7389	0.043*
C17	0.0491 (2)	0.3758 (2)	0.43304 (18)	0.0356 (5)
C19	0.2746 (2)	0.4186 (2)	0.48183 (18)	0.0396 (5)
H19	0.3484	0.4132	0.5338	0.047*
C21	0.18924 (19)	0.48116 (19)	0.32559 (15)	0.0282 (4)
C22	0.05870 (19)	0.4349 (2)	0.33929 (17)	0.0326 (5)
C24	0.0355 (2)	0.5197 (2)	0.19095 (17)	0.0393 (5)
H24	−0.0021	0.5484	0.1263	0.047*
C26	0.39753 (18)	0.4774 (2)	0.13725 (15)	0.0290 (4)
C27	0.3671 (2)	0.3761 (2)	0.05959 (16)	0.0322 (5)
C28	0.4589 (2)	0.2887 (2)	0.04330 (18)	0.0429 (5)
H28	0.4371	0.2224	−0.0090	0.051*
C29	0.5839 (2)	0.3008 (3)	0.1056 (2)	0.0478 (6)
H29	0.6455	0.2410	0.0965	0.057*
C30	0.6173 (2)	0.4008 (3)	0.1809 (2)	0.0495 (6)
H30	0.7022	0.4093	0.2215	0.059*
C31	0.5248 (2)	0.4892 (2)	0.19642 (17)	0.0398 (5)
H31	0.5486	0.5570	0.2471	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0334 (3)	0.0680 (4)	0.0641 (4)	0.0061 (3)	0.0164 (3)	0.0127 (3)
Cl2	0.0409 (3)	0.0498 (4)	0.0706 (4)	−0.0040 (3)	0.0228 (3)	0.0140 (3)
S1	0.0250 (2)	0.0325 (3)	0.0309 (3)	0.0005 (2)	0.00197 (19)	−0.0021 (2)
S2	0.0309 (3)	0.0314 (3)	0.0304 (3)	0.0021 (2)	0.0060 (2)	0.0050 (2)
O1	0.0349 (8)	0.0312 (8)	0.0451 (9)	−0.0042 (6)	0.0067 (6)	0.0009 (7)
O2	0.0343 (8)	0.0509 (10)	0.0332 (8)	0.0074 (7)	−0.0038 (6)	−0.0041 (7)
O3	0.0367 (8)	0.0559 (11)	0.0569 (10)	0.0116 (8)	0.0042 (8)	0.0077 (9)
O4	0.0723 (12)	0.0616 (12)	0.0418 (10)	0.0071 (10)	0.0082 (9)	0.0178 (9)
O5	0.0444 (8)	0.0444 (9)	0.0360 (8)	0.0108 (7)	0.0079 (7)	0.0159 (7)
O6	0.0454 (9)	0.0379 (9)	0.0480 (9)	−0.0064 (7)	0.0069 (7)	−0.0073 (7)
O7	0.0319 (8)	0.0582 (11)	0.0482 (9)	0.0036 (8)	−0.0018 (7)	0.0009 (8)
O8	0.0699 (13)	0.1006 (17)	0.0438 (11)	0.0237 (12)	−0.0109 (9)	−0.0293 (11)
N2	0.0436 (11)	0.0514 (13)	0.0603 (13)	0.0045 (10)	0.0126 (10)	0.0212 (11)
N4	0.0382 (10)	0.0404 (11)	0.0492 (11)	0.0080 (9)	0.0064 (8)	0.0125 (9)
N7	0.0316 (9)	0.0404 (11)	0.0415 (10)	0.0076 (8)	0.0038 (8)	0.0086 (8)
N9	0.0275 (8)	0.0324 (10)	0.0333 (9)	0.0040 (7)	0.0050 (7)	0.0040 (7)
N16	0.0384 (10)	0.0354 (10)	0.0334 (10)	−0.0020 (8)	−0.0039 (8)	−0.0018 (8)
N18	0.0408 (10)	0.0407 (11)	0.0416 (11)	0.0053 (9)	0.0089 (8)	0.0131 (9)
N20	0.0270 (8)	0.0409 (11)	0.0328 (9)	0.0050 (8)	0.0018 (7)	0.0070 (8)
N23	0.0255 (9)	0.0576 (13)	0.0402 (11)	0.0048 (8)	0.0030 (8)	0.0080 (9)
N25	0.0247 (8)	0.0407 (10)	0.0267 (8)	0.0062 (7)	0.0036 (7)	0.0072 (7)
N32	0.0416 (10)	0.0380 (11)	0.0344 (10)	0.0059 (9)	−0.0034 (8)	−0.0013 (8)
C1	0.0314 (11)	0.0464 (14)	0.0392 (12)	0.0017 (10)	0.0040 (9)	0.0042 (10)
C3	0.0484 (14)	0.0478 (15)	0.0629 (17)	0.0086 (12)	0.0090 (12)	0.0244 (13)
C5	0.0313 (10)	0.0326 (11)	0.0300 (11)	0.0010 (9)	0.0025 (8)	0.0017 (9)
C6	0.0290 (10)	0.0370 (12)	0.0328 (11)	0.0028 (9)	0.0018 (8)	0.0038 (9)
C8	0.0333 (11)	0.0370 (12)	0.0380 (12)	0.0063 (9)	0.0034 (9)	0.0087 (10)
C10	0.0252 (9)	0.0301 (11)	0.0303 (10)	−0.0019 (8)	0.0056 (8)	−0.0009 (8)
C11	0.0254 (10)	0.0315 (11)	0.0349 (11)	−0.0024 (8)	0.0016 (8)	0.0019 (9)
C12	0.0353 (11)	0.0427 (13)	0.0323 (11)	−0.0029 (10)	0.0060 (9)	−0.0043 (10)
C13	0.0382 (11)	0.0382 (13)	0.0465 (13)	0.0031 (10)	0.0136 (10)	−0.0057 (10)
C14	0.0368 (11)	0.0366 (13)	0.0531 (14)	0.0093 (10)	0.0109 (10)	0.0058 (11)
C15	0.0347 (11)	0.0385 (12)	0.0360 (12)	0.0053 (9)	0.0056 (9)	0.0051 (10)
C17	0.0337 (11)	0.0309 (12)	0.0449 (13)	0.0022 (9)	0.0140 (10)	0.0067 (10)
C19	0.0353 (11)	0.0474 (14)	0.0367 (12)	0.0079 (10)	0.0009 (9)	0.0114 (10)
C21	0.0276 (10)	0.0286 (11)	0.0292 (10)	0.0050 (8)	0.0061 (8)	0.0012 (8)
C22	0.0266 (10)	0.0347 (12)	0.0374 (11)	0.0025 (9)	0.0068 (8)	0.0040 (9)
C24	0.0275 (10)	0.0553 (15)	0.0357 (12)	0.0113 (10)	−0.0001 (9)	0.0076 (11)
C26	0.0259 (9)	0.0358 (11)	0.0268 (10)	0.0029 (8)	0.0062 (8)	0.0083 (9)
C27	0.0313 (10)	0.0375 (12)	0.0288 (10)	0.0054 (9)	0.0034 (8)	0.0084 (9)
C28	0.0493 (13)	0.0434 (14)	0.0397 (13)	0.0146 (11)	0.0122 (10)	0.0063 (10)
C29	0.0393 (12)	0.0632 (17)	0.0484 (14)	0.0233 (12)	0.0163 (11)	0.0208 (13)
C30	0.0276 (11)	0.0752 (19)	0.0481 (14)	0.0081 (12)	0.0040 (10)	0.0210 (14)
C31	0.0281 (10)	0.0561 (15)	0.0346 (12)	−0.0015 (10)	0.0026 (9)	0.0070 (11)

Cl1—C1	1.728 (2)	N25—C24	1.394 (3)
Cl2—C17	1.720 (2)	N32—C27	1.468 (3)
S1—O1	1.4226 (15)	C1—C6	1.378 (3)
S1—O2	1.4178 (15)	C3—H3	0.9300
S1—N9	1.6794 (16)	C5—C6	1.397 (3)
S1—C10	1.769 (2)	C8—H8	0.9300
S2—O5	1.4177 (15)	C10—C11	1.402 (3)
S2—O6	1.4150 (16)	C10—C15	1.385 (3)
S2—N25	1.6833 (16)	C11—C12	1.374 (3)
S2—C26	1.777 (2)	C12—H12	0.9300
O3—N16	1.216 (2)	C12—C13	1.379 (3)
O4—N16	1.221 (2)	C13—H13	0.9300
O7—N32	1.214 (2)	C13—C14	1.376 (3)
O8—N32	1.217 (2)	C14—H14	0.9300
N2—C1	1.317 (3)	C14—C15	1.387 (3)
N2—C3	1.340 (3)	C15—H15	0.9300
N4—C3	1.336 (3)	C17—C22	1.380 (3)
N4—C5	1.322 (3)	C19—H19	0.9300
N7—C6	1.391 (3)	C21—C22	1.399 (3)
N7—C8	1.293 (3)	C24—H24	0.9300
N9—C5	1.393 (3)	C26—C27	1.400 (3)
N9—C8	1.395 (3)	C26—C31	1.385 (3)
N16—C11	1.471 (3)	C27—C28	1.379 (3)
N18—C17	1.320 (3)	C28—H28	0.9300
N18—C19	1.337 (3)	C28—C29	1.382 (3)
N20—C19	1.339 (3)	C29—H29	0.9300
N20—C21	1.325 (2)	C29—C30	1.374 (4)
N23—C22	1.387 (3)	C30—H30	0.9300
N23—C24	1.290 (3)	C30—C31	1.390 (3)
N25—C21	1.388 (2)	C31—H31	0.9300
O1—S1—N9	104.73 (9)	C6—C1—Cl1	120.78 (17)
O1—S1—C10	108.86 (9)	C8—N7—C6	104.56 (17)
O2—S1—O1	121.88 (10)	C8—N9—S1	125.05 (14)
O2—S1—N9	106.39 (9)	C10—C11—N16	122.06 (18)
O2—S1—C10	107.43 (9)	C10—C15—C14	120.1 (2)
O3—N16—O4	124.65 (19)	C10—C15—H15	119.9
O3—N16—C11	117.33 (18)	C11—C10—S1	124.35 (16)
O4—N16—C11	117.93 (18)	C11—C12—H12	120.3
O5—S2—N25	105.10 (8)	C11—C12—C13	119.4 (2)
O5—S2—C26	111.24 (9)	C12—C11—N16	116.63 (19)
O6—S2—O5	121.33 (10)	C12—C11—C10	121.2 (2)
O6—S2—N25	106.67 (9)	C12—C13—H13	119.8
O6—S2—C26	106.90 (10)	C13—C12—H12	120.3
O7—N32—O8	123.88 (19)	C13—C14—H14	119.8
O7—N32—C27	118.70 (17)	C13—C14—C15	120.4 (2)
O8—N32—C27	117.42 (18)	C14—C13—C12	120.3 (2)
N2—C1—Cl1	117.83 (17)	C14—C13—H13	119.8
N2—C1—C6	121.4 (2)	C14—C15—H15	119.9
N2—C3—H3	115.9	C15—C10—S1	116.41 (15)
N4—C3—N2	128.3 (2)	C15—C10—C11	118.50 (19)
N4—C3—H3	115.9	C15—C14—H14	119.8
N4—C5—N9	128.60 (18)	C17—N18—C19	117.34 (18)
N4—C5—C6	126.78 (19)	C17—C22—N23	133.58 (18)
N7—C6—C5	111.24 (17)	C17—C22—C21	115.02 (18)
N7—C8—N9	113.85 (19)	C21—N20—C19	111.42 (17)
N7—C8—H8	123.1	C21—N25—S2	128.61 (13)
N9—S1—C10	106.61 (9)	C21—N25—C24	105.71 (16)
N9—C5—C6	104.60 (17)	C22—C17—Cl2	120.68 (17)
N9—C8—H8	123.1	C24—N23—C22	104.34 (17)
N18—C17—Cl2	118.10 (16)	C24—N25—S2	125.56 (14)
N18—C17—C22	121.22 (18)	C26—C27—N32	122.17 (18)
N18—C19—N20	128.4 (2)	C26—C31—C30	120.7 (2)
N18—C19—H19	115.8	C26—C31—H31	119.7
N20—C19—H19	115.8	C27—C26—S2	126.17 (15)
N20—C21—N25	128.98 (17)	C27—C28—H28	120.3
N20—C21—C22	126.52 (18)	C27—C28—C29	119.3 (2)
N23—C22—C21	111.38 (17)	C28—C27—N32	116.2 (2)
N23—C24—N25	114.08 (18)	C28—C27—C26	121.6 (2)
N23—C24—H24	123.0	C28—C29—H29	119.9
N25—S2—C26	104.22 (9)	C29—C28—H28	120.3
N25—C21—C22	104.48 (16)	C29—C30—H30	119.9
N25—C24—H24	123.0	C29—C30—C31	120.3 (2)
C1—N2—C3	117.3 (2)	C30—C29—C28	120.2 (2)
C1—C6—N7	133.91 (19)	C30—C29—H29	119.9
C1—C6—C5	114.85 (19)	C30—C31—H31	119.7
C5—N4—C3	111.40 (19)	C31—C26—S2	115.78 (17)
C5—N9—S1	128.59 (14)	C31—C26—C27	117.84 (19)
C5—N9—C8	105.75 (16)	C31—C30—H30	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O6	0.93	2.60	3.222 (3)	125
C15—H15···O2	0.93	2.41	2.814 (3)	106
C24—H24···O7i	0.93	2.41	3.327 (3)	170
C28—H28···O2ii	0.93	2.56	3.469 (3)	165
C30—H30···N23iii	0.93	2.62	3.489 (3)	155
C31—H31···O6	0.93	2.36	2.794 (3)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O6	0.93	2.60	3.222 (3)	125
C24—H24⋯O7i	0.93	2.41	3.327 (3)	170
C28—H28⋯O2ii	0.93	2.56	3.469 (3)	165
C30—H30⋯N23iii	0.93	2.62	3.489 (3)	155

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