4-(Acetyl­amino)phen­yl benzene­sulfonate

The phenyl and acetyl­amino­phenyl rings of the title compound, C₁₄H₁₃NO₄S, are at an angle of 71.57 (5)°, with the acetyl­amino group rotated by 16.3 (1)° from coplanarity with the ring to which it is attached. The structure is stabilized by the presence of N—H...O hydrogen bonds which create infinite one-dimensional chains along [010]; weak C—H...O inter­actions are also present.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT391_ALERT_3_B Deviating Methyl C20     H-C-H Bond Angle ......      99.50 Deg.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.869     1.000
            Tmin(prime) and Tmax expected:      0.920     0.951
            RR(prime) =      0.898
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 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 (I) was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure of (I) is shown in Fig. 1 with selected geometric parameters provided in Table 1. The S—C, S—O and S=O bond lengths are comparable with 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 provided 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 employed to assign + or -synclinal (sc) and +antiperiplanar (ap) conformations. The C2–S1–O10–C11 torsion angle of -61.6 (1)° corresponds to +synclinal conformation. The dihedral angle between the mean planes of the phenyl and acetylaminophenyl C₆ rings of 71.58 (8)° shows that the two rings are not coplanar. This is similar to that reported by us for other aromatic sulfonates (Manivannan et al. 2005 & references cited therein). The acetylamino group (N17 C18 O19 C20) is twisted by 16.3 (1)° from the mean plane of the phenyl ring (C11—C16) to which it is attached.

The crystal structure of (I) is stabilized by the presence of an intermolecular N—H···O hydrogen bond, along with several weak C—H···O interactions (Desiraju et al., 1999) (Table 2, Fig. 3). The symmetry related N—H···O interactions generate a cooperative infinite one-dimensional chain along [010], while the C7—H7···O10 (-x + 1, -y + 1, -z + 1) interactions generate an R²₂(10) motif (Etter, et al., 1990; Bernstein et al., 1995).

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); Bernstein et al. (1995); Etter (1990); Desiraju et al. (1999); Jiang et al. (1990); Narayanan & Krakow (1983); Sheldrick (1998b); Spungin et al. (1992); Tharakan et al. (1992); Yachi et al. (1989).

S2. Experimental

Benzenesulfonyl chloride (10 mmol), dissolved in acetone, was added dropwise to N-(4-hydroxyphenyl)acetamide (10 mmol) in aqueous NaOH (8 ml, 5%) with constant stirring. The precipitant (6.0 mmol, yield 60%) was filtered and recrystallized from aqueous ethanol.

S3. Refinement

Hydrogen atoms were positioned geometrically (aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å and N—H = 0.88 Å) and refined using a riding model. The H atom isotropic displacement parameters were fixed; U_iso(aromatic H) = 1.2 x U_eq of the parent atom; U_iso(methyl H) = 1.5 x U_eq of the parent atom; U_iso(N—H) = 1.2 x U_eq of the parent atom.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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 asymmetric unit of (I) with the atoms labelled and displacement ellipsoids depicted at the 50% probability level for the 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 viewed down the a-axis. Dashed lines represent the weak C—H···O interactions.

N-[4-(Acetylamino)phenyl]benzenesulfonate

Crystal data

C14H13NO4S	F(000) = 608
Mr = 291.31	Dx = 1.436 Mg m^−3
Monoclinic, P21/n	Melting point = 386–387 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.9028 (14) Å	Cell parameters from 5029 reflections
b = 8.7768 (9) Å	θ = 2.8–29.9°
c = 13.7394 (15) Å	µ = 0.25 mm^−1
β = 110.144 (4)°	T = 120 K
V = 1347.5 (3) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer	3637 independent reflections
Radiation source: fine-focus sealed tube	2983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8 pixels mm^-1	θmax = 30.0°, θmin = 2.0°
ω scans	h = −16→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1998a)	k = −11→11
Tmin = 0.869, Tmax = 1.000	l = −19→18
9274 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 0.484P] where P = (Fo^2 + 2Fc^2)/3
3637 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.39 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	0.68262 (3)	0.63484 (4)	0.48846 (3)	0.02158 (11)
C2	0.75999 (13)	0.57481 (16)	0.61551 (11)	0.0203 (3)
C3	0.88245 (14)	0.60072 (18)	0.65761 (12)	0.0264 (3)
C4	0.94228 (15)	0.5596 (2)	0.75990 (13)	0.0304 (3)
C5	0.88100 (15)	0.4921 (2)	0.81739 (12)	0.0297 (3)
C6	0.75873 (16)	0.4664 (2)	0.77403 (13)	0.0308 (4)
C7	0.69649 (14)	0.50892 (19)	0.67272 (12)	0.0274 (3)
O8	0.76729 (10)	0.68778 (12)	0.44310 (9)	0.0277 (2)
O9	0.58457 (10)	0.73088 (13)	0.48467 (9)	0.0304 (3)
O10	0.61972 (9)	0.48512 (12)	0.43025 (8)	0.0229 (2)
C11	0.69032 (12)	0.35872 (16)	0.42162 (11)	0.0203 (3)
C12	0.76458 (13)	0.36714 (17)	0.36377 (11)	0.0225 (3)
C13	0.82522 (14)	0.23759 (17)	0.35126 (11)	0.0228 (3)
C14	0.81121 (13)	0.10049 (17)	0.39774 (11)	0.0204 (3)
C15	0.73370 (14)	0.09522 (17)	0.45465 (12)	0.0232 (3)
C16	0.67308 (13)	0.22412 (17)	0.46683 (12)	0.0236 (3)
N17	0.86890 (12)	−0.03536 (15)	0.38809 (10)	0.0231 (3)
C18	0.96450 (13)	−0.05347 (18)	0.35576 (12)	0.0249 (3)
O19	1.01465 (12)	0.05343 (14)	0.33170 (12)	0.0423 (3)
C20	1.00092 (16)	−0.2161 (2)	0.35039 (14)	0.0291 (3)
H3	0.9265 (18)	0.651 (2)	0.6176 (16)	0.035 (5)*
H4	1.0294 (19)	0.578 (2)	0.7907 (16)	0.037 (5)*
H5	0.9233 (19)	0.461 (2)	0.8887 (16)	0.041 (6)*
H6	0.720 (2)	0.421 (2)	0.8139 (17)	0.044 (6)*
H7	0.6112 (19)	0.493 (2)	0.6414 (15)	0.034 (5)*
H12	0.7745 (16)	0.462 (2)	0.3331 (14)	0.026 (5)*
H13	0.8753 (17)	0.244 (2)	0.3133 (14)	0.028 (5)*
H15	0.7254 (15)	0.002 (2)	0.4843 (13)	0.021 (4)*
H16	0.6220 (17)	0.221 (2)	0.5066 (15)	0.032 (5)*
H17	0.8453 (17)	−0.117 (2)	0.4077 (14)	0.027 (5)*
H20A	0.949 (2)	−0.270 (2)	0.3034 (17)	0.040*
H20B	1.0039 (19)	−0.273 (2)	0.4107 (17)	0.040*
H20C	1.076 (2)	−0.222 (2)	0.3411 (16)	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02313 (18)	0.01753 (17)	0.02454 (18)	0.00093 (13)	0.00880 (14)	0.00177 (13)
C2	0.0214 (7)	0.0166 (6)	0.0234 (7)	−0.0002 (5)	0.0083 (5)	−0.0008 (5)
C3	0.0236 (7)	0.0261 (7)	0.0302 (8)	−0.0047 (6)	0.0100 (6)	0.0006 (6)
C4	0.0228 (7)	0.0334 (9)	0.0318 (8)	−0.0030 (7)	0.0055 (6)	−0.0006 (7)
C5	0.0317 (8)	0.0338 (8)	0.0227 (7)	0.0035 (7)	0.0082 (6)	0.0007 (6)
C6	0.0308 (8)	0.0373 (9)	0.0289 (8)	−0.0001 (7)	0.0160 (7)	0.0052 (7)
C7	0.0224 (7)	0.0320 (8)	0.0296 (8)	−0.0013 (6)	0.0112 (6)	0.0019 (6)
O8	0.0348 (6)	0.0221 (5)	0.0297 (6)	−0.0057 (5)	0.0155 (5)	0.0014 (4)
O9	0.0313 (6)	0.0255 (6)	0.0337 (6)	0.0101 (5)	0.0102 (5)	0.0035 (5)
O10	0.0194 (5)	0.0217 (5)	0.0263 (5)	−0.0003 (4)	0.0061 (4)	−0.0012 (4)
C11	0.0177 (6)	0.0203 (7)	0.0208 (6)	−0.0009 (5)	0.0039 (5)	−0.0026 (5)
C12	0.0247 (7)	0.0221 (7)	0.0206 (6)	−0.0034 (6)	0.0075 (6)	0.0018 (5)
C13	0.0241 (7)	0.0245 (7)	0.0217 (7)	−0.0032 (6)	0.0104 (6)	−0.0006 (5)
C14	0.0199 (6)	0.0209 (7)	0.0205 (6)	−0.0040 (5)	0.0070 (5)	−0.0035 (5)
C15	0.0264 (7)	0.0195 (7)	0.0265 (7)	−0.0048 (6)	0.0126 (6)	−0.0002 (6)
C16	0.0230 (7)	0.0243 (7)	0.0261 (7)	−0.0045 (6)	0.0119 (6)	−0.0016 (6)
N17	0.0266 (6)	0.0186 (6)	0.0270 (6)	−0.0030 (5)	0.0129 (5)	−0.0018 (5)
C18	0.0229 (7)	0.0277 (7)	0.0244 (7)	−0.0002 (6)	0.0086 (6)	−0.0019 (6)
O19	0.0382 (7)	0.0309 (6)	0.0720 (10)	0.0004 (6)	0.0370 (7)	0.0054 (6)
C20	0.0255 (8)	0.0287 (8)	0.0325 (8)	0.0019 (6)	0.0090 (7)	−0.0044 (7)

Geometric parameters (Å, º)

S1—O8	1.4326 (11)	C11—C16	1.382 (2)
S1—O9	1.4260 (11)	C12—C13	1.389 (2)
S1—O10	1.5857 (11)	C12—H12	0.958 (19)
S1—C2	1.7509 (15)	C13—C14	1.399 (2)
C2—C3	1.389 (2)	C13—H13	0.920 (19)
C2—C7	1.390 (2)	C14—C15	1.401 (2)
C3—C4	1.387 (2)	C14—N17	1.4047 (19)
C3—H3	0.99 (2)	C15—C16	1.383 (2)
C4—C5	1.380 (2)	C15—H15	0.937 (18)
C4—H4	0.99 (2)	C16—H16	0.947 (19)
C5—C6	1.388 (2)	N17—C18	1.366 (2)
C5—H5	0.97 (2)	N17—H17	0.84 (2)
C6—C7	1.384 (2)	C18—O19	1.2173 (19)
C6—H6	0.92 (2)	C18—C20	1.501 (2)
C7—H7	0.97 (2)	C20—H20A	0.86 (2)
O10—C11	1.4211 (17)	C20—H20B	0.96 (2)
C11—C12	1.379 (2)	C20—H20C	0.94 (2)
O8—S1—O9	118.81 (7)	C11—C12—C13	119.40 (14)
O8—S1—O10	109.27 (6)	C11—C12—H12	120.1 (11)
O9—S1—O10	103.48 (6)	C13—C12—H12	120.5 (11)
O8—S1—C2	108.91 (7)	C12—C13—C14	119.93 (14)
O9—S1—C2	110.92 (7)	C12—C13—H13	119.0 (12)
O10—S1—C2	104.38 (6)	C14—C13—H13	121.1 (12)
C3—C2—C7	121.97 (14)	C13—C14—C15	119.22 (14)
C3—C2—S1	118.81 (12)	C13—C14—N17	123.24 (13)
C7—C2—S1	119.16 (11)	C15—C14—N17	117.52 (13)
C4—C3—C2	118.57 (15)	C16—C15—C14	120.81 (14)
C4—C3—H3	119.7 (12)	C16—C15—H15	121.8 (11)
C2—C3—H3	121.6 (12)	C14—C15—H15	117.4 (11)
C5—C4—C3	120.25 (15)	C11—C16—C15	118.71 (14)
C5—C4—H4	120.5 (12)	C11—C16—H16	120.6 (12)
C3—C4—H4	119.2 (12)	C15—C16—H16	120.7 (12)
C4—C5—C6	120.45 (15)	C18—N17—C14	128.20 (13)
C4—C5—H5	120.4 (12)	C18—N17—H17	114.3 (13)
C6—C5—H5	119.2 (12)	C14—N17—H17	117.4 (13)
C7—C6—C5	120.46 (15)	O19—C18—N17	122.68 (15)
C7—C6—H6	120.8 (14)	O19—C18—C20	122.87 (14)
C5—C6—H6	118.7 (14)	N17—C18—C20	114.44 (14)
C6—C7—C2	118.29 (15)	C18—C20—H20A	114.2 (14)
C6—C7—H7	121.6 (12)	C18—C20—H20B	112.1 (13)
C2—C7—H7	120.1 (12)	H20A—C20—H20B	99.6 (19)
C11—O10—S1	119.93 (9)	C18—C20—H20C	111.4 (13)
C12—C11—C16	121.90 (14)	H20A—C20—H20C	109.6 (19)
C12—C11—O10	121.39 (13)	H20B—C20—H20C	109.4 (18)
C16—C11—O10	116.49 (13)
O9—S1—C2—C3	−125.43 (13)	S1—O10—C11—C12	−66.20 (16)
O8—S1—C2—C3	7.12 (14)	S1—O10—C11—C16	119.02 (12)
O10—S1—C2—C3	123.73 (12)	C16—C11—C12—C13	−0.8 (2)
O9—S1—C2—C7	51.76 (14)	O10—C11—C12—C13	−175.30 (13)
O8—S1—C2—C7	−175.69 (12)	C11—C12—C13—C14	−0.4 (2)
O10—S1—C2—C7	−59.08 (13)	C12—C13—C14—C15	1.4 (2)
C7—C2—C3—C4	−0.2 (2)	C12—C13—C14—N17	179.59 (13)
S1—C2—C3—C4	176.95 (12)	C13—C14—C15—C16	−1.2 (2)
C2—C3—C4—C5	1.1 (3)	N17—C14—C15—C16	−179.52 (14)
C3—C4—C5—C6	−0.8 (3)	C12—C11—C16—C15	1.0 (2)
C4—C5—C6—C7	−0.4 (3)	O10—C11—C16—C15	175.73 (13)
C5—C6—C7—C2	1.3 (3)	C14—C15—C16—C11	0.1 (2)
C3—C2—C7—C6	−1.0 (2)	C13—C14—N17—C18	16.3 (2)
S1—C2—C7—C6	−178.09 (13)	C15—C14—N17—C18	−165.51 (15)
O9—S1—O10—C11	−177.78 (10)	C14—N17—C18—O19	1.2 (3)
O8—S1—O10—C11	54.72 (12)	C14—N17—C18—C20	−177.61 (14)
C2—S1—O10—C11	−61.64 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8	0.99 (2)	2.51 (2)	2.892 (2)	102.6 (14)
C12—H12···O8	0.958 (19)	2.513 (18)	3.0140 (19)	112.7 (13)
C13—H13···O19	0.920 (19)	2.308 (19)	2.861 (2)	118.3 (14)
N17—H17···O8^i	0.84 (2)	2.09 (2)	2.9272 (17)	173.3 (18)
C6—H6···O19^ii	0.92 (2)	2.55 (2)	3.269 (2)	135.5 (18)
C7—H7···O10^iii	0.97 (2)	2.59 (2)	3.5360 (19)	166.6 (16)
C16—H16···O9^iii	0.947 (19)	2.539 (19)	3.3783 (19)	147.9 (15)

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