4-Nitro­phenyl benzene­sulfonate

In the structure of the title compound, C₁₂H₉NO₅S, the phenyl and 4-nitro­phenyl rings are not coplanar, the dihedral angle being 53.91 (4)°. The structure contains weak inter­molecular C—H...O hydrogen bonds and face-to-face π–π inter­actions between symmetry-related phenyl rings (separation 3.664 Å).

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.093
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.799     1.000
            Tmin(prime) and Tmax expected:      0.917     0.945
            RR(prime) =      0.823
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.945
            Tmax scaled      0.945 Tmin scaled      0.755

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989) and in many other fields (Spungin et al., 1992, Tharakan et al.,1992, Alford et al., 1991, Jiang et al., 1990, Narayanan & Krakow, 1983). An X-ray study of the title compound was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure of the title compound, C₁₂H₉NO₅S, is shown in Fig. 1 with selected torsion angles provided in Table 1. The S—C, S—O and S=O bond lengths are all comparable to those found in related structures previously reported by our research group (Manivannan et al. 2005 & references cited therein).

A Newman projection along the O10—S1 bond is shown in Fig. 2. Using C11 as a reference point, the orientations of the two sulfonyl oxygen atoms (O8 and O9) and the phenyl carbon (C2) have been deduced from the corresponding torsion angles (C11–O10–S1–O8/O9/C2). Helical nomenclature is followed in assigning + or -synclinal and -antiperiplanar conformations. The C2–S1–O10–C11 torsion angle of 75.2 (1)° corresponds to +synclinal conformation. The dihedral angle between the mean planes of the phenyl and 4-nitrophenyl rings of 53.91 (4)° shows that the two rings are not coplanar. This is similar to the situation reported by us for other aromatic sulfonates (Manivannan et al. 2005 & references cited therein).

The crystal structure of the title compound is stabilized by the presence of weak intermolecular C—H···O (Fig. 3) (Desiraju et al., 1999) (Table 2) and π···π interactions. The symmetry related phenyl rings (C2—C7) [2 - x, 1 - y, -z] interact in a face to face manner with a separation of 3.664 Å.

Related literature

For a detailed account of the molecular and supramolecular architectures of aromatic sulfonates, see Manivannan et al. (2005) and references cited therein.

For related literature, see: Alford et al. (1991); Desiraju & Steiner (1999); Jiang et al. (1990); Narayanan & Krakow (1983); Spungin et al. (1992); Tharakan et al. (1992); Yachi et al. (1989).

S2. Experimental

Benzenesulfonyl chloride (10 mmol), dissolved in acetone (10 ml), was added dropwise to 4-nitrophenol (10 mmol) in aqueous NaOH (8 ml, 5%) with constant stirring. The precipitate (6.5 mmol, yield 65%) was filtered and recrystallized from an acetone/ethanol (1:10) mixture.

S3. Refinement

All H atoms were located in difference maps and their positions and isotropic displacement parameters freely refined. The range of refined C—H distances was 0.91 (2) - 0.99 (2) Å.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the title compound, with the atoms labelled and displacement ellipsoids drawn at the 50% probability level for all non-H atoms. H-atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A Newman projection along the O10—S1 bond with C11 as a reference point, +/-sc = +/-synclinal, -ap = -antiperiplanar.
	Fig. 3. The molecular packing. Dashed lines represent the weak C—H···O interactions.

4-Nitrophenyl benzenesulfonate

Crystal data

C12H9NO5S	F(000) = 576
Mr = 279.26	Dx = 1.529 Mg m^−3
Monoclinic, P21/c	Melting point = 340–342 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.015 (3) Å	Cell parameters from 8716 reflections
b = 10.852 (4) Å	θ = 2.6–30.0°
c = 11.396 (4) Å	µ = 0.28 mm^−1
β = 101.651 (8)°	T = 120 K
V = 1213.0 (7) Å^3	Block, colourless
Z = 4	0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer	3437 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8 pixels mm^-1	θmax = 30.3°, θmin = 2.1°
ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	k = −15→15
Tmin = 0.799, Tmax = 1.000	l = −15→15
23602 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.5272P] where P = (Fo^2 + 2Fc^2)/3
3437 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.88009 (4)	0.64514 (3)	0.20115 (3)	0.02644 (10)
C2	0.84763 (14)	0.53463 (13)	0.08707 (13)	0.0241 (3)
C3	0.77611 (15)	0.56938 (15)	−0.02609 (13)	0.0270 (3)
C4	0.75429 (15)	0.48225 (16)	−0.11640 (14)	0.0298 (3)
C5	0.80280 (15)	0.36285 (15)	−0.09411 (14)	0.0302 (3)
C6	0.87286 (16)	0.32943 (15)	0.01874 (15)	0.0312 (3)
C7	0.89596 (15)	0.41514 (14)	0.11100 (14)	0.0278 (3)
O8	0.98137 (11)	0.59973 (11)	0.29756 (9)	0.0316 (2)
O9	0.89369 (13)	0.76432 (10)	0.15216 (10)	0.0361 (3)
O10	0.73797 (11)	0.65581 (10)	0.24513 (9)	0.0296 (2)
C11	0.70056 (15)	0.56091 (13)	0.31653 (13)	0.0248 (3)
C12	0.75723 (16)	0.55939 (14)	0.43750 (13)	0.0270 (3)
C13	0.71255 (15)	0.47233 (14)	0.50931 (13)	0.0273 (3)
C14	0.61342 (14)	0.38957 (13)	0.45633 (13)	0.0250 (3)
C15	0.55842 (15)	0.38921 (15)	0.33496 (14)	0.0278 (3)
C16	0.60276 (15)	0.47702 (15)	0.26344 (13)	0.0285 (3)
N17	0.56559 (13)	0.29760 (13)	0.53293 (12)	0.0313 (3)
O18	0.59839 (14)	0.31087 (12)	0.64123 (11)	0.0432 (3)
O19	0.49469 (14)	0.21269 (13)	0.48477 (12)	0.0470 (3)
H3	0.7429 (19)	0.6529 (17)	−0.0389 (16)	0.034 (5)*
H4	0.7063 (19)	0.5073 (18)	−0.1976 (17)	0.035 (5)*
H5	0.7882 (19)	0.3017 (17)	−0.1583 (16)	0.035 (5)*
H6	0.910 (2)	0.2527 (19)	0.0343 (17)	0.040 (5)*
H7	0.9479 (19)	0.3944 (18)	0.1900 (17)	0.037 (5)*
H12	0.8242 (18)	0.6151 (17)	0.4690 (16)	0.032 (5)*
H13	0.7501 (19)	0.4703 (17)	0.5940 (17)	0.037 (5)*
H15	0.4911 (19)	0.3330 (17)	0.3031 (16)	0.033 (5)*
H16	0.5667 (19)	0.4819 (17)	0.1794 (17)	0.036 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03116 (19)	0.02337 (18)	0.02263 (18)	−0.00350 (14)	0.00035 (13)	0.00245 (14)
C2	0.0232 (6)	0.0247 (7)	0.0236 (7)	−0.0038 (5)	0.0031 (5)	0.0018 (5)
C3	0.0258 (7)	0.0282 (8)	0.0256 (7)	0.0013 (6)	0.0020 (5)	0.0038 (6)
C4	0.0238 (7)	0.0379 (9)	0.0262 (7)	−0.0013 (6)	0.0014 (6)	0.0000 (6)
C5	0.0244 (7)	0.0327 (8)	0.0332 (8)	−0.0067 (6)	0.0053 (6)	−0.0058 (7)
C6	0.0285 (7)	0.0246 (8)	0.0395 (9)	−0.0027 (6)	0.0047 (6)	0.0006 (6)
C7	0.0261 (7)	0.0270 (8)	0.0287 (7)	−0.0019 (6)	0.0015 (6)	0.0054 (6)
O8	0.0310 (6)	0.0351 (6)	0.0252 (5)	−0.0033 (5)	−0.0024 (4)	0.0015 (4)
O9	0.0514 (7)	0.0252 (6)	0.0289 (6)	−0.0094 (5)	0.0014 (5)	0.0040 (4)
O10	0.0357 (6)	0.0248 (5)	0.0275 (5)	0.0053 (4)	0.0044 (4)	0.0047 (4)
C11	0.0287 (7)	0.0218 (7)	0.0239 (7)	0.0052 (5)	0.0052 (5)	0.0003 (5)
C12	0.0315 (7)	0.0238 (7)	0.0243 (7)	−0.0010 (6)	0.0023 (6)	−0.0053 (6)
C13	0.0309 (7)	0.0298 (8)	0.0202 (7)	0.0025 (6)	0.0028 (6)	−0.0033 (6)
C14	0.0251 (7)	0.0245 (7)	0.0263 (7)	0.0052 (5)	0.0073 (5)	−0.0002 (5)
C15	0.0237 (7)	0.0301 (8)	0.0283 (7)	0.0002 (6)	0.0024 (6)	−0.0052 (6)
C16	0.0274 (7)	0.0343 (8)	0.0217 (7)	0.0029 (6)	0.0001 (6)	−0.0024 (6)
N17	0.0275 (6)	0.0331 (7)	0.0346 (7)	0.0027 (5)	0.0093 (5)	0.0035 (6)
O18	0.0566 (8)	0.0446 (7)	0.0301 (6)	−0.0018 (6)	0.0129 (6)	0.0064 (5)
O19	0.0420 (7)	0.0467 (8)	0.0516 (8)	−0.0171 (6)	0.0079 (6)	0.0026 (6)

Geometric parameters (Å, º)

S1—O8	1.4243 (11)	O10—C11	1.4094 (18)
S1—O9	1.4262 (12)	C11—C12	1.381 (2)
S1—O10	1.6057 (12)	C11—C16	1.384 (2)
S1—C2	1.7503 (15)	C12—C13	1.382 (2)
C2—C7	1.392 (2)	C12—H12	0.920 (19)
C2—C3	1.395 (2)	C13—C14	1.384 (2)
C3—C4	1.382 (2)	C13—H13	0.962 (18)
C3—H3	0.967 (19)	C14—C15	1.382 (2)
C4—C5	1.389 (2)	C14—N17	1.469 (2)
C4—H4	0.991 (19)	C15—C16	1.384 (2)
C5—C6	1.383 (2)	C15—H15	0.927 (19)
C5—H5	0.976 (19)	C16—H16	0.954 (19)
C6—C7	1.388 (2)	N17—O18	1.2198 (18)
C6—H6	0.91 (2)	N17—O19	1.2236 (19)
C7—H7	0.971 (19)
O8—S1—O9	120.42 (7)	C2—C7—H7	119.9 (11)
O8—S1—O10	108.79 (7)	C11—O10—S1	118.90 (9)
O9—S1—O10	102.56 (7)	C12—C11—C16	122.72 (14)
O8—S1—C2	109.42 (7)	C12—C11—O10	118.79 (13)
O9—S1—C2	110.41 (7)	C16—C11—O10	118.39 (13)
O10—S1—C2	103.76 (6)	C11—C12—C13	118.84 (14)
C7—C2—C3	121.77 (14)	C11—C12—H12	120.1 (11)
C7—C2—S1	119.19 (11)	C13—C12—H12	121.0 (11)
C3—C2—S1	119.02 (12)	C12—C13—C14	118.35 (14)
C4—C3—C2	118.55 (14)	C12—C13—H13	120.1 (11)
C4—C3—H3	122.1 (11)	C14—C13—H13	121.6 (11)
C2—C3—H3	119.4 (11)	C15—C14—C13	122.99 (14)
C3—C4—C5	120.34 (15)	C15—C14—N17	118.77 (14)
C3—C4—H4	118.8 (11)	C13—C14—N17	118.24 (13)
C5—C4—H4	120.9 (11)	C14—C15—C16	118.50 (14)
C6—C5—C4	120.51 (15)	C14—C15—H15	120.4 (11)
C6—C5—H5	119.3 (11)	C16—C15—H15	121.1 (11)
C4—C5—H5	120.2 (11)	C11—C16—C15	118.58 (14)
C5—C6—C7	120.28 (15)	C11—C16—H16	119.6 (12)
C5—C6—H6	122.0 (12)	C15—C16—H16	121.8 (12)
C7—C6—H6	117.6 (12)	O18—N17—O19	123.79 (14)
C6—C7—C2	118.55 (14)	O18—N17—C14	117.88 (14)
C6—C7—H7	121.5 (11)	O19—N17—C14	118.33 (13)
O8—S1—C2—C7	13.37 (14)	S1—O10—C11—C12	79.98 (15)
O9—S1—C2—C7	148.12 (12)	S1—O10—C11—C16	−103.52 (14)
O10—S1—C2—C7	−102.61 (12)	C16—C11—C12—C13	−1.5 (2)
O8—S1—C2—C3	−165.46 (11)	O10—C11—C12—C13	174.88 (13)
O9—S1—C2—C3	−30.71 (14)	C11—C12—C13—C14	0.5 (2)
O10—S1—C2—C3	78.56 (12)	C12—C13—C14—C15	0.8 (2)
C7—C2—C3—C4	−0.6 (2)	C12—C13—C14—N17	−179.67 (13)
S1—C2—C3—C4	178.25 (11)	C13—C14—C15—C16	−1.2 (2)
C2—C3—C4—C5	0.1 (2)	N17—C14—C15—C16	179.26 (13)
C3—C4—C5—C6	0.3 (2)	C12—C11—C16—C15	1.0 (2)
C4—C5—C6—C7	−0.2 (2)	O10—C11—C16—C15	−175.31 (13)
C5—C6—C7—C2	−0.2 (2)	C14—C15—C16—C11	0.3 (2)
C3—C2—C7—C6	0.6 (2)	C15—C14—N17—O18	−168.62 (14)
S1—C2—C7—C6	−178.16 (11)	C13—C14—N17—O18	11.8 (2)
O8—S1—O10—C11	−41.26 (12)	C15—C14—N17—O19	10.9 (2)
O9—S1—O10—C11	−169.86 (10)	C13—C14—N17—O19	−168.63 (14)
C2—S1—O10—C11	75.15 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O8	0.971 (19)	2.533 (19)	2.921 (2)	103.8 (13)
C7—H7···O9^i	0.971 (19)	2.567 (19)	3.479 (2)	156.5 (15)
C12—H12···O9^ii	0.920 (19)	2.442 (19)	3.188 (2)	138.2 (14)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2.