3-[4-(Acetamido)­benzene­sulfonamido]­benzoic acid

In the title compound, C₁₅H₁₄N₂O₅S, the dihedral angle between the aromatic rings is 63.20 (11) Å. The crystal structure displays classical inter­molecular O—H...O hydrogen bonding typical for carb­oxy­lic acids, forming centrosymmetric dimers. These dimers are further connected by N—H...O and C—H...O hydrogen bonds to form an extended network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.150
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uso(min) ...       6.25 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C1     -C6            1.37 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          9
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         22

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        200 Deg.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

Sulfonamides are well known in literature for their potential as biologically active compounds (Hanson et al., 1999; Moree et al.,1991; Rough et al., 1998). These have been reported to display anti-hypertensive, anti-convulsant, herbicidal and anti-malarial activities (Esteve & Bidal, 2002; Soledade et al., 2006; Xiao & Timberlake, 2000; Lee & Lee, 2002). In addition the sulfonamide unit has been found in a number of compounds possessing anti-HIV (Selnam et al.,2001), anti-inflammatory (Ratish et al., 2009) and anti-microbial (Ozbek et al., 2007; Parari et al., 2008) activities.

In continuation of our work regarding the synthesis of various sulfur containing heterocycles (Arshad et al., 2008; Khan et al., 2009), the structure of 3-({[4-(acetylamino)phenyl]sulfonyl}amino)benzoic acid (I) has been determined. Bond lengths and bond angles of the title molecule (Fig 1) are similar to those in related compounds (Gowda et al., 2007a,b,c; Haider et al., 2009) and are within normal ranges (Allen et al., 1987). In the crystal structure, each molecule is linked to an adjacent one through classical O5—H7···O4 intermolecular hydrogen bonds forming centrosymmetric dimers typical of carboxylic acids, Table 1. These dimers are further connected by N—H···O and C—H···O hydrogen bonds to form an extended network, Fig 2.

Related literature

For the synthesis of related compounds, see: Khan et al. (2009); Arshad et al. (2008). For the biological activity of sulfonamides, see: Esteve & Bidal (2002); Hanson et al. (1999); Lee & Lee (2002); Moree et al. (1991); Ozbek et al. (2007); Parari et al. (2008); Ratish et al. (2009); Rough et al. (1998); Selnam et al. (2001); Soledade et al. (2006); Xiao & Timberlake (2000). For related structures, see: Gowda et al. (2007a,b,c); Haider et al. (2009). For bond-length data, see: Allen et al. (1987).

S2. Experimental

To an aqueous solution (10.0 ml) of 4-amino benzoic acid (1.0 g; 7.3 mmoles) maintained at pH 9 with aqueous sodium bicarbonate solution, 4-(acetylamino)benzenesulfonyl chloride (2.21 g, 9.48 mmol) was added. Contents were stirred at room temperature until the complete consumption of the sulfonyl chloride (as indicated by TLC). The pH of the reaction mixture was changed to 1 using hydrochloric acid (1 M) and the precipitate obtained was filtered, washed with water and dried. The resulting solid was recrystallized from methanol to get suitable crystals.

S3. Refinement

All hydrogen atoms were identified in the difference map. Those bonded to O, C and N were fixed in ideal positions and treated as riding on their parent atoms. The following distances were used: methyl C—H 0.98Å; aromatic C—H 0.95Å; N—H 0.86 Å.

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

3-[4-(Acetamido)benzenesulfonamido]benzoic acid

Crystal data

C15H14N2O5S	Z = 2
Mr = 334.34	F(000) = 348
Triclinic, P1	Dx = 1.423 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9829 (3) Å	Cell parameters from 5086 reflections
b = 8.4143 (3) Å	θ = 2.6–27.5°
c = 12.6554 (5) Å	µ = 0.23 mm^−1
α = 70.888 (2)°	T = 296 K
β = 81.553 (2)°	Needles, dark brown
γ = 77.104 (2)°	0.24 × 0.18 × 0.14 mm
V = 780.44 (5) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	2928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 28.3°, θmin = 2.7°
φ and ω scans	h = −9→10
13620 measured reflections	k = −10→11
3835 independent reflections	l = −16→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0733P)^2 + 0.3675P] where P = (Fo^2 + 2Fc^2)/3
3835 reflections	(Δ/σ)max = 0.034
210 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.47 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	0.36529 (6)	0.60917 (7)	0.20813 (4)	0.03843 (18)
N1	0.1928 (2)	0.5659 (2)	0.28924 (14)	0.0397 (4)
H1	0.1346	0.4996	0.2775	0.048*
O2	0.50673 (18)	0.5656 (2)	0.27558 (14)	0.0503 (4)
O1	0.3732 (2)	0.5277 (2)	0.12378 (13)	0.0489 (4)
C4	0.2682 (3)	1.1815 (3)	0.03783 (17)	0.0380 (5)
C1	0.3286 (2)	0.8313 (3)	0.14368 (17)	0.0373 (4)
N3	0.2462 (2)	1.3587 (2)	−0.01344 (14)	0.0424 (4)
H3	0.2964	1.4127	0.0158	0.051*
O16	0.0723 (2)	1.3984 (2)	−0.14922 (15)	0.0601 (5)
C7	0.1369 (3)	0.6366 (3)	0.37967 (17)	0.0370 (4)
O5	−0.3233 (3)	0.9184 (3)	0.57458 (17)	0.0786 (7)
C14	0.1564 (3)	1.4568 (3)	−0.10295 (18)	0.0421 (5)
O4	−0.3591 (3)	0.9200 (4)	0.40422 (19)	0.0954 (9)
C9	−0.0886 (3)	0.7910 (3)	0.47573 (18)	0.0437 (5)
C12	0.2427 (3)	0.6086 (3)	0.46374 (19)	0.0511 (6)
H12	0.3535	0.5447	0.4610	0.061*
C8	−0.0291 (3)	0.7287 (3)	0.38531 (18)	0.0411 (5)
H8	−0.1007	0.7490	0.3288	0.049*
C10	0.0194 (3)	0.7651 (3)	0.5583 (2)	0.0530 (6)
H10	−0.0194	0.8083	0.6182	0.064*
C11	0.1851 (3)	0.6745 (4)	0.5510 (2)	0.0593 (7)
H11	0.2586	0.6580	0.6058	0.071*
C15	0.1669 (3)	1.6414 (3)	−0.1392 (2)	0.0518 (6)
H15A	0.0989	1.7018	−0.2019	0.078*
H15B	0.2847	1.6541	−0.1608	0.078*
H15C	0.1237	1.6877	−0.0784	0.078*
C6	0.2468 (5)	0.9002 (4)	0.0475 (3)	0.0854 (11)
H6	0.2102	0.8281	0.0172	0.102*
C5	0.2170 (5)	1.0723 (4)	−0.0058 (3)	0.0823 (11)
H5	0.1618	1.1157	−0.0720	0.099*
C13	−0.2682 (3)	0.8827 (4)	0.4850 (2)	0.0570 (7)
C2	0.3792 (5)	0.9385 (4)	0.1877 (2)	0.0757 (10)
H2	0.4357	0.8940	0.2533	0.091*
C3	0.3476 (5)	1.1122 (4)	0.1358 (2)	0.0760 (10)
H4	0.3807	1.1841	0.1679	0.091*
H7	−0.4296	0.9779	0.5730	0.30 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0298 (3)	0.0460 (3)	0.0443 (3)	−0.0019 (2)	−0.0027 (2)	−0.0237 (2)
N1	0.0351 (9)	0.0448 (10)	0.0441 (10)	−0.0086 (7)	−0.0023 (7)	−0.0196 (8)
O2	0.0323 (8)	0.0616 (10)	0.0597 (10)	0.0010 (7)	−0.0102 (7)	−0.0257 (8)
O1	0.0472 (9)	0.0552 (10)	0.0543 (9)	−0.0056 (7)	0.0007 (7)	−0.0346 (8)
C4	0.0325 (10)	0.0502 (12)	0.0366 (10)	−0.0100 (9)	−0.0007 (8)	−0.0199 (9)
C1	0.0319 (9)	0.0462 (12)	0.0393 (11)	−0.0091 (8)	0.0007 (8)	−0.0208 (9)
N3	0.0442 (10)	0.0486 (11)	0.0414 (10)	−0.0124 (8)	−0.0087 (8)	−0.0185 (8)
O16	0.0570 (10)	0.0703 (12)	0.0606 (11)	−0.0117 (9)	−0.0257 (8)	−0.0210 (9)
C7	0.0352 (10)	0.0405 (11)	0.0341 (10)	−0.0052 (8)	−0.0019 (8)	−0.0112 (9)
O5	0.0565 (11)	0.1177 (18)	0.0653 (12)	0.0201 (11)	−0.0089 (9)	−0.0554 (12)
C14	0.0339 (10)	0.0570 (13)	0.0385 (11)	−0.0055 (9)	0.0001 (8)	−0.0221 (10)
O4	0.0579 (12)	0.156 (2)	0.0790 (14)	0.0398 (13)	−0.0287 (11)	−0.0740 (15)
C9	0.0404 (11)	0.0497 (13)	0.0409 (12)	−0.0025 (9)	−0.0047 (9)	−0.0169 (10)
C12	0.0372 (11)	0.0699 (16)	0.0423 (12)	0.0038 (11)	−0.0099 (9)	−0.0182 (11)
C8	0.0372 (10)	0.0485 (12)	0.0376 (11)	−0.0019 (9)	−0.0089 (8)	−0.0146 (9)
C10	0.0522 (13)	0.0692 (16)	0.0402 (12)	−0.0033 (12)	−0.0059 (10)	−0.0244 (12)
C11	0.0489 (13)	0.089 (2)	0.0423 (13)	−0.0005 (13)	−0.0159 (10)	−0.0255 (13)
C15	0.0544 (14)	0.0541 (14)	0.0452 (13)	−0.0014 (11)	−0.0027 (10)	−0.0190 (11)
C6	0.130 (3)	0.0517 (16)	0.096 (2)	−0.0114 (17)	−0.075 (2)	−0.0271 (15)
C5	0.129 (3)	0.0534 (16)	0.080 (2)	−0.0076 (17)	−0.071 (2)	−0.0206 (14)
C13	0.0486 (13)	0.0706 (17)	0.0553 (15)	0.0080 (12)	−0.0088 (11)	−0.0347 (13)
C2	0.128 (3)	0.0570 (16)	0.0561 (16)	−0.0268 (17)	−0.0497 (17)	−0.0113 (13)
C3	0.129 (3)	0.0529 (15)	0.0634 (17)	−0.0294 (17)	−0.0507 (18)	−0.0142 (13)

Geometric parameters (Å, º)

S1—O2	1.4252 (15)	O4—C13	1.255 (3)
S1—O1	1.4331 (15)	C9—C10	1.383 (3)
S1—N1	1.6264 (17)	C9—C8	1.390 (3)
S1—C1	1.753 (2)	C9—C13	1.477 (3)
N1—C7	1.428 (2)	C12—C11	1.369 (3)
N1—H1	0.8600	C12—H12	0.9300
C4—C3	1.368 (3)	C8—H8	0.9300
C4—C5	1.372 (3)	C10—C11	1.378 (4)
C4—N3	1.399 (3)	C10—H10	0.9300
C1—C2	1.359 (3)	C11—H11	0.9300
C1—C6	1.359 (3)	C15—H15A	0.9600
N3—C14	1.357 (3)	C15—H15B	0.9600
N3—H3	0.8600	C15—H15C	0.9600
O16—C14	1.219 (3)	C6—C5	1.365 (4)
C7—C8	1.383 (3)	C6—H6	0.9300
C7—C12	1.383 (3)	C5—H5	0.9300
O5—C13	1.260 (3)	C2—C3	1.374 (4)
O5—H7	0.8831	C2—H2	0.9300
C14—C15	1.487 (3)	C3—H4	0.9300
O2—S1—O1	119.27 (9)	C7—C8—C9	119.82 (19)
O2—S1—N1	108.91 (9)	C7—C8—H8	120.1
O1—S1—N1	105.07 (9)	C9—C8—H8	120.1
O2—S1—C1	107.95 (10)	C11—C10—C9	119.4 (2)
O1—S1—C1	108.32 (10)	C11—C10—H10	120.3
N1—S1—C1	106.68 (9)	C9—C10—H10	120.3
C7—N1—S1	120.87 (14)	C12—C11—C10	120.6 (2)
C7—N1—H1	119.6	C12—C11—H11	119.7
S1—N1—H1	119.6	C10—C11—H11	119.7
C3—C4—C5	117.9 (2)	C14—C15—H15A	109.5
C3—C4—N3	118.54 (19)	C14—C15—H15B	109.5
C5—C4—N3	123.5 (2)	H15A—C15—H15B	109.5
C2—C1—C6	118.4 (2)	C14—C15—H15C	109.5
C2—C1—S1	121.67 (18)	H15A—C15—H15C	109.5
C6—C1—S1	119.95 (17)	H15B—C15—H15C	109.5
C14—N3—C4	128.83 (18)	C1—C6—C5	121.8 (2)
C14—N3—H3	115.6	C1—C6—H6	119.1
C4—N3—H3	115.6	C5—C6—H6	119.1
C8—C7—C12	119.55 (19)	C6—C5—C4	120.2 (2)
C8—C7—N1	119.05 (18)	C6—C5—H5	119.9
C12—C7—N1	121.34 (19)	C4—C5—H5	119.9
C13—O5—H7	113.2	O4—C13—O5	123.1 (2)
O16—C14—N3	122.6 (2)	O4—C13—C9	118.9 (2)
O16—C14—C15	122.7 (2)	O5—C13—C9	118.0 (2)
N3—C14—C15	114.73 (19)	C1—C2—C3	120.4 (2)
C10—C9—C8	120.1 (2)	C1—C2—H2	119.8
C10—C9—C13	119.8 (2)	C3—C2—H2	119.8
C8—C9—C13	120.1 (2)	C4—C3—C2	121.2 (2)
C11—C12—C7	120.4 (2)	C4—C3—H4	119.4
C11—C12—H12	119.8	C2—C3—H4	119.4
C7—C12—H12	119.8
O2—S1—N1—C7	55.28 (18)	C13—C9—C8—C7	−177.2 (2)
O1—S1—N1—C7	−175.87 (15)	C8—C9—C10—C11	−1.1 (4)
C1—S1—N1—C7	−60.99 (17)	C13—C9—C10—C11	177.9 (3)
O2—S1—C1—C2	−23.6 (3)	C7—C12—C11—C10	2.0 (4)
O1—S1—C1—C2	−154.0 (2)	C9—C10—C11—C12	−0.8 (4)
N1—S1—C1—C2	93.4 (2)	C2—C1—C6—C5	0.8 (5)
O2—S1—C1—C6	156.7 (2)	S1—C1—C6—C5	−179.4 (3)
O1—S1—C1—C6	26.3 (3)	C1—C6—C5—C4	−0.7 (6)
N1—S1—C1—C6	−86.4 (3)	C3—C4—C5—C6	−0.6 (5)
C3—C4—N3—C14	−172.3 (3)	N3—C4—C5—C6	178.3 (3)
C5—C4—N3—C14	8.9 (4)	C10—C9—C13—O4	173.0 (3)
S1—N1—C7—C8	124.75 (19)	C8—C9—C13—O4	−8.0 (4)
S1—N1—C7—C12	−57.9 (3)	C10—C9—C13—O5	−7.6 (4)
C4—N3—C14—O16	3.6 (3)	C8—C9—C13—O5	171.4 (3)
C4—N3—C14—C15	−177.18 (19)	C6—C1—C2—C3	0.2 (5)
C8—C7—C12—C11	−1.3 (4)	S1—C1—C2—C3	−179.5 (3)
N1—C7—C12—C11	−178.6 (2)	C5—C4—C3—C2	1.6 (5)
C12—C7—C8—C9	−0.6 (3)	N3—C4—C3—C2	−177.3 (3)
N1—C7—C8—C9	176.8 (2)	C1—C2—C3—C4	−1.5 (5)
C10—C9—C8—C7	1.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H7···O4^i	0.88	1.74	2.617 (4)	170
N1—H1···O16^ii	0.86	2.31	2.860 (2)	122
N3—H3···O1^iii	0.86	2.13	2.974 (2)	165
C11—H11···O2^iv	0.93	2.59	3.379 (3)	143

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