4-(Tosyl­amino)benzoic acid

In the mol­ecule of the title compound, C₁₄H₁₃NO₄S, the dihedral angle between the two benzene rings is 34.7°. The C—N—S—C torsion angle in the central part of the mol­ecule is 65.67°. The mol­ecular packing involves centrosymmetrically related carboxyl groups connected by O—H...O hydrogen bonds forming dimers, whereas inter­molecular N—H...O=S hydrogen bonds connect mol­ecules into a chain along the [011] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.119
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

4-(Tosylamino)benzoic acid

Crystal data

C14H13NO4S	F(000) = 608
Mr = 291.31	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 10798 reflections
a = 5.1626 (10) Å	θ = 3.1–25.5°
b = 13.178 (3) Å	µ = 0.25 mm^−1
c = 20.003 (4) Å	T = 293 K
β = 92.11 (3)°	Bar, white
V = 1360.0 (5) Å^3	0.45 × 0.14 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	2491 independent reflections
Radiation source: rotating anode	2182 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
oscillation scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.896, Tmax = 0.971	k = −15→15
10798 measured reflections	l = −24→22

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0861P)^2 + 0.1493P] where P = (Fo^2 + 2Fc^2)/3
2491 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.54 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
N1	0.2127 (3)	0.53802 (10)	0.21023 (7)	0.0369 (3)
H1A	0.0927	0.4943	0.2013	0.044*
S1	0.40751 (7)	0.52607 (3)	0.27695 (2)	0.03728 (18)
O1	0.3306 (3)	0.43405 (10)	0.30837 (7)	0.0513 (4)
O2	0.6664 (2)	0.53770 (10)	0.25470 (7)	0.0504 (4)
O3	0.2551 (3)	0.95783 (9)	0.05169 (7)	0.0518 (4)
H3B	0.3107	1.0048	0.0294	0.078*
O4	0.6109 (3)	0.88246 (10)	0.01612 (7)	0.0516 (4)
C1	0.0939 (6)	0.88795 (19)	0.44025 (12)	0.0766 (7)
H1C	−0.0389	0.8676	0.4698	0.115*
H1D	0.0259	0.9382	0.4096	0.115*
H1E	0.2376	0.9159	0.4659	0.115*
C2	0.1832 (4)	0.79736 (16)	0.40178 (9)	0.0536 (5)
C3	0.3763 (5)	0.80551 (16)	0.35561 (11)	0.0618 (6)
H3A	0.4547	0.8681	0.3492	0.074*
C4	0.4548 (4)	0.72298 (16)	0.31901 (10)	0.0553 (5)
H4A	0.5852	0.7297	0.2884	0.066*
C5	0.3363 (3)	0.62963 (13)	0.32849 (8)	0.0389 (4)
C6	0.1442 (4)	0.61960 (15)	0.37465 (9)	0.0489 (5)
H6A	0.0657	0.5571	0.3812	0.059*
C7	0.0711 (4)	0.70281 (16)	0.41059 (9)	0.0553 (5)
H7A	−0.0572	0.6957	0.4417	0.066*
C8	0.2500 (3)	0.62381 (12)	0.16756 (8)	0.0340 (4)
C9	0.0918 (3)	0.70790 (14)	0.17023 (9)	0.0425 (4)
H9A	−0.0460	0.7085	0.1989	0.051*
C10	0.1375 (3)	0.79134 (13)	0.13046 (9)	0.0431 (4)
H10A	0.0296	0.8477	0.1321	0.052*
C11	0.3447 (3)	0.79099 (12)	0.08809 (7)	0.0336 (3)
C12	0.4995 (3)	0.70545 (13)	0.08451 (8)	0.0413 (4)
H12A	0.6365	0.7044	0.0556	0.050*
C13	0.4515 (4)	0.62198 (13)	0.12350 (8)	0.0424 (4)
H13A	0.5541	0.5643	0.1203	0.051*
C14	0.4101 (3)	0.88239 (12)	0.04917 (8)	0.0365 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0294 (7)	0.0367 (8)	0.0450 (8)	−0.0076 (5)	0.0046 (6)	0.0066 (5)
S1	0.0271 (3)	0.0384 (3)	0.0468 (3)	0.00104 (15)	0.00649 (17)	0.01220 (16)
O1	0.0484 (8)	0.0419 (7)	0.0641 (8)	0.0042 (6)	0.0097 (6)	0.0214 (6)
O2	0.0267 (6)	0.0604 (9)	0.0646 (8)	0.0032 (5)	0.0088 (6)	0.0099 (6)
O3	0.0547 (8)	0.0387 (7)	0.0637 (8)	0.0119 (6)	0.0231 (6)	0.0166 (6)
O4	0.0503 (8)	0.0428 (7)	0.0636 (8)	0.0060 (6)	0.0268 (6)	0.0133 (6)
C1	0.101 (2)	0.0609 (15)	0.0688 (14)	0.0074 (13)	0.0164 (13)	0.0003 (11)
C2	0.0623 (12)	0.0527 (12)	0.0459 (10)	0.0034 (9)	0.0040 (8)	0.0052 (8)
C3	0.0731 (14)	0.0469 (12)	0.0666 (12)	−0.0164 (10)	0.0174 (10)	0.0041 (9)
C4	0.0536 (11)	0.0525 (12)	0.0611 (11)	−0.0143 (9)	0.0184 (9)	0.0049 (9)
C5	0.0311 (9)	0.0449 (10)	0.0408 (8)	−0.0033 (7)	0.0037 (6)	0.0089 (7)
C6	0.0493 (11)	0.0498 (11)	0.0485 (10)	−0.0097 (8)	0.0128 (8)	0.0099 (8)
C7	0.0545 (12)	0.0606 (13)	0.0520 (11)	−0.0038 (9)	0.0185 (9)	0.0064 (9)
C8	0.0300 (8)	0.0341 (8)	0.0379 (7)	−0.0034 (6)	0.0020 (6)	0.0041 (6)
C9	0.0292 (8)	0.0465 (10)	0.0527 (9)	0.0044 (7)	0.0146 (7)	0.0100 (7)
C10	0.0356 (9)	0.0395 (9)	0.0549 (10)	0.0098 (7)	0.0134 (7)	0.0092 (7)
C11	0.0325 (8)	0.0336 (8)	0.0350 (7)	0.0000 (6)	0.0039 (6)	0.0015 (6)
C12	0.0437 (9)	0.0383 (9)	0.0429 (9)	0.0063 (7)	0.0164 (7)	0.0033 (7)
C13	0.0466 (10)	0.0329 (9)	0.0488 (9)	0.0093 (7)	0.0166 (7)	0.0041 (7)
C14	0.0377 (9)	0.0341 (9)	0.0382 (8)	0.0017 (7)	0.0069 (6)	0.0024 (6)

Geometric parameters (Å, º)

N1—C8	1.4340 (19)	C4—C5	1.390 (3)
N1—S1	1.6490 (15)	C4—H4A	0.9300
N1—H1A	0.8600	C5—C6	1.386 (2)
S1—O1	1.4287 (13)	C6—C7	1.372 (3)
S1—O2	1.4323 (13)	C6—H6A	0.9300
S1—C5	1.7574 (18)	C7—H7A	0.9300
O3—C14	1.278 (2)	C8—C9	1.379 (2)
O3—H3B	0.8200	C8—C13	1.388 (2)
O4—C14	1.2502 (19)	C9—C10	1.383 (2)
C1—C2	1.502 (3)	C9—H9A	0.9300
C1—H1C	0.9600	C10—C11	1.389 (2)
C1—H1D	0.9600	C10—H10A	0.9300
C1—H1E	0.9600	C11—C12	1.385 (2)
C2—C7	1.388 (3)	C11—C14	1.480 (2)
C2—C3	1.388 (3)	C12—C13	1.376 (2)
C3—C4	1.380 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C8—N1—S1	117.75 (10)	C7—C6—C5	119.37 (17)
C8—N1—H1A	121.1	C7—C6—H6A	120.3
S1—N1—H1A	121.1	C5—C6—H6A	120.3
O1—S1—O2	120.33 (8)	C6—C7—C2	121.80 (17)
O1—S1—N1	105.43 (8)	C6—C7—H7A	119.1
O2—S1—N1	106.66 (8)	C2—C7—H7A	119.1
O1—S1—C5	109.49 (8)	C9—C8—C13	119.83 (15)
O2—S1—C5	108.47 (8)	C9—C8—N1	121.18 (14)
N1—S1—C5	105.44 (7)	C13—C8—N1	118.99 (14)
C14—O3—H3B	109.5	C8—C9—C10	120.19 (15)
C2—C1—H1C	109.5	C8—C9—H9A	119.9
C2—C1—H1D	109.5	C10—C9—H9A	119.9
H1C—C1—H1D	109.5	C9—C10—C11	120.01 (15)
C2—C1—H1E	109.5	C9—C10—H10A	120.0
H1C—C1—H1E	109.5	C11—C10—H10A	120.0
H1D—C1—H1E	109.5	C12—C11—C10	119.53 (15)
C7—C2—C3	117.85 (19)	C12—C11—C14	119.47 (14)
C7—C2—C1	120.7 (2)	C10—C11—C14	120.94 (14)
C3—C2—C1	121.4 (2)	C13—C12—C11	120.33 (15)
C4—C3—C2	121.61 (19)	C13—C12—H12A	119.8
C4—C3—H3A	119.2	C11—C12—H12A	119.8
C2—C3—H3A	119.2	C12—C13—C8	120.04 (15)
C3—C4—C5	119.06 (18)	C12—C13—H13A	120.0
C3—C4—H4A	120.5	C8—C13—H13A	120.0
C5—C4—H4A	120.5	O4—C14—O3	123.56 (15)
C6—C5—C4	120.30 (18)	O4—C14—C11	119.24 (14)
C6—C5—S1	119.14 (14)	O3—C14—C11	117.19 (14)
C4—C5—S1	120.31 (13)
C8—N1—S1—O1	−178.53 (12)	C1—C2—C7—C6	178.1 (2)
C8—N1—S1—O2	−49.53 (13)	S1—N1—C8—C9	−101.33 (17)
C8—N1—S1—C5	65.67 (13)	S1—N1—C8—C13	77.89 (17)
C7—C2—C3—C4	0.4 (3)	C13—C8—C9—C10	−1.7 (3)
C1—C2—C3—C4	−178.5 (2)	N1—C8—C9—C10	177.51 (15)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C11	−0.6 (3)
C3—C4—C5—C6	−0.7 (3)	C9—C10—C11—C12	2.0 (3)
C3—C4—C5—S1	173.52 (16)	C9—C10—C11—C14	−175.01 (16)
O1—S1—C5—C6	−23.76 (16)	C10—C11—C12—C13	−1.1 (3)
O2—S1—C5—C6	−156.84 (14)	C14—C11—C12—C13	175.92 (15)
N1—S1—C5—C6	89.22 (15)	C11—C12—C13—C8	−1.1 (3)
O1—S1—C5—C4	161.90 (15)	C9—C8—C13—C12	2.6 (3)
O2—S1—C5—C4	28.83 (17)	N1—C8—C13—C12	−176.66 (15)
N1—S1—C5—C4	−85.11 (16)	C12—C11—C14—O4	−3.3 (2)
C4—C5—C6—C7	0.4 (3)	C10—C11—C14—O4	173.73 (16)
S1—C5—C6—C7	−173.94 (15)	C12—C11—C14—O3	176.93 (15)
C5—C6—C7—C2	0.4 (3)	C10—C11—C14—O3	−6.0 (2)
C3—C2—C7—C6	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.86	2.55	2.9882 (19)	113
O3—H3B···O4^ii	0.82	1.80	2.6109 (18)	171

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