2-(Naphthalene-2-sulfonamido)-3-phenyl-propanoic acid.

In the title compound, C(19)H(17)NO(4)S, the phenyl ring and the naphthalene ring system are oriented at a dihedral angle of 4.12 (2)° and the mol-ecule adopts a U-shaped conformation. The C(c)-C-N-S (c = carb-oxy) torsion angle is 90.98 (15)°. In the crystal, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds, resulting in (100) chains incorporating centrosymmetric R(2) (2)(14) and R(2) (2)(10) loops. Weak aromatic π-π stacking is also observed [centroid-centroid separations = 3.963 (2) and 3.932 (2) Å].

Related literature

For the synthesis and related structures, see: Arshad et al. (2012 ▶); Khan et al. (2012 ▶).

Experimental

Crystal data

C19H17NO4S

M = 355.40

Monoclinic,

a = 8.0694 (2) Å

b = 15.2168 (4) Å

c = 14.0996 (3) Å

β = 92.505 (2)°

V = 1729.64 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.87 mm−1

T = 296 K

0.29 × 0.10 × 0.09 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.784, T max = 1.000

13588 measured reflections

3486 independent reflections

2813 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.03

3486 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and X-SEED (Barbour, 2001 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000081/hb7020sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000081/hb7020Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000081/hb7020Isup3.cml

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

C19H17NO4S	F(000) = 744
Mr = 355.40	Dx = 1.365 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 5975 reflections
a = 8.0694 (2) Å	θ = 3.1–74.6°
b = 15.2168 (4) Å	µ = 1.87 mm−1
c = 14.0996 (3) Å	T = 296 K
β = 92.505 (2)°	Prismatic, colorless
V = 1729.64 (7) Å3	0.29 × 0.10 × 0.09 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer	3486 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2813 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
ω scans	θmax = 74.7°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −9→9
Tmin = 0.784, Tmax = 1.000	k = −18→18
13588 measured reflections	l = −17→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.4657P] where P = (Fo2 + 2Fc2)/3
3486 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.31495 (6)	0.52701 (3)	0.68873 (3)	0.05113 (16)
O1	0.4041 (2)	0.60690 (9)	0.70303 (11)	0.0687 (4)
O2	0.14144 (17)	0.53082 (11)	0.66184 (11)	0.0707 (4)
O3	0.24930 (18)	0.47490 (10)	0.41829 (10)	0.0647 (4)
O4	0.05674 (17)	0.39149 (11)	0.48022 (11)	0.0671 (4)
N1	0.40035 (19)	0.47399 (10)	0.60505 (10)	0.0470 (4)
C1	0.3324 (2)	0.46054 (13)	0.79139 (13)	0.0521 (4)
C2	0.1937 (3)	0.41529 (18)	0.81402 (16)	0.0749 (6)
H2	0.0955	0.4223	0.7778	0.090*
C3	0.1997 (4)	0.3582 (2)	0.8920 (2)	0.1020 (10)
H3	0.1058	0.3263	0.9066	0.122*
C4	0.3406 (4)	0.3492 (2)	0.9463 (2)	0.0980 (9)
H4	0.3416	0.3119	0.9985	0.118*
C5	0.4860 (3)	0.39491 (16)	0.92563 (15)	0.0706 (6)
C6	0.4857 (2)	0.45189 (13)	0.84526 (13)	0.0524 (4)
C7	0.6347 (3)	0.49537 (16)	0.82581 (15)	0.0623 (5)
H7	0.6387	0.5319	0.7731	0.075*
C8	0.7732 (3)	0.4843 (2)	0.88355 (19)	0.0839 (8)
H8	0.8705	0.5135	0.8697	0.101*
C9	0.7708 (4)	0.4296 (2)	0.9636 (2)	0.0969 (9)
H9	0.8656	0.4234	1.0030	0.116*
C10	0.6320 (4)	0.3866 (2)	0.98330 (18)	0.0909 (9)
H10	0.6320	0.3502	1.0363	0.109*
C11	0.3160 (2)	0.39725 (12)	0.56401 (12)	0.0454 (4)
H11	0.2472	0.3704	0.6117	0.054*
C12	0.4398 (2)	0.32926 (13)	0.53018 (13)	0.0535 (4)
H12A	0.3793	0.2812	0.4996	0.064*
H12B	0.5084	0.3561	0.4834	0.064*
C13	0.5497 (2)	0.29330 (12)	0.61016 (13)	0.0516 (4)
C14	0.4856 (4)	0.23896 (18)	0.6765 (2)	0.0874 (8)
H14	0.3741	0.2234	0.6713	0.105*
C15	0.5838 (5)	0.2070 (2)	0.7509 (2)	0.1202 (12)
H15	0.5374	0.1712	0.7961	0.144*
C16	0.7457 (5)	0.2268 (2)	0.7590 (2)	0.1056 (11)
H16	0.8113	0.2041	0.8091	0.127*
C17	0.8139 (3)	0.28037 (19)	0.6937 (2)	0.0895 (9)
H17	0.9262	0.2943	0.6992	0.107*
C18	0.7150 (3)	0.31431 (15)	0.61838 (17)	0.0665 (5)
H18	0.7613	0.3511	0.5739	0.080*
C19	0.2050 (2)	0.42710 (13)	0.47926 (13)	0.0491 (4)
H1N	0.499 (3)	0.4785 (14)	0.6034 (16)	0.059*
H1O	−0.004 (3)	0.4135 (16)	0.4325 (18)	0.074*

	U11	U22	U33	U12	U13	U23
S1	0.0438 (3)	0.0605 (3)	0.0478 (3)	0.00944 (19)	−0.01179 (18)	−0.00627 (19)
O1	0.0815 (10)	0.0540 (8)	0.0685 (9)	0.0020 (7)	−0.0201 (8)	−0.0057 (7)
O2	0.0465 (8)	0.0973 (11)	0.0667 (9)	0.0235 (7)	−0.0148 (6)	−0.0138 (8)
O3	0.0578 (9)	0.0813 (10)	0.0536 (8)	−0.0026 (7)	−0.0119 (6)	0.0181 (7)
O4	0.0452 (8)	0.0972 (11)	0.0578 (8)	−0.0087 (7)	−0.0101 (6)	0.0008 (8)
N1	0.0368 (7)	0.0587 (9)	0.0449 (8)	−0.0018 (7)	−0.0044 (6)	−0.0024 (6)
C1	0.0458 (10)	0.0687 (12)	0.0417 (9)	−0.0002 (8)	−0.0003 (7)	−0.0060 (8)
C2	0.0590 (13)	0.1014 (18)	0.0645 (13)	−0.0162 (12)	0.0052 (10)	−0.0047 (12)
C3	0.097 (2)	0.123 (2)	0.0877 (19)	−0.0394 (19)	0.0219 (17)	0.0136 (18)
C4	0.120 (3)	0.106 (2)	0.0686 (16)	−0.0131 (19)	0.0126 (16)	0.0233 (15)
C5	0.0856 (16)	0.0774 (14)	0.0485 (11)	0.0091 (12)	−0.0012 (10)	0.0035 (10)
C6	0.0518 (11)	0.0639 (11)	0.0412 (9)	0.0067 (8)	−0.0035 (7)	−0.0039 (8)
C7	0.0483 (11)	0.0830 (14)	0.0547 (11)	0.0030 (10)	−0.0083 (9)	0.0009 (10)
C8	0.0529 (14)	0.117 (2)	0.0803 (16)	0.0082 (13)	−0.0203 (12)	−0.0049 (15)
C9	0.085 (2)	0.127 (2)	0.0751 (17)	0.0339 (19)	−0.0363 (15)	−0.0053 (16)
C10	0.112 (2)	0.102 (2)	0.0563 (13)	0.0313 (18)	−0.0201 (14)	0.0092 (13)
C11	0.0428 (9)	0.0535 (10)	0.0394 (8)	−0.0005 (7)	−0.0033 (7)	0.0017 (7)
C12	0.0599 (11)	0.0562 (10)	0.0439 (9)	0.0092 (9)	−0.0029 (8)	0.0030 (8)
C13	0.0578 (11)	0.0459 (9)	0.0503 (10)	0.0072 (8)	−0.0056 (8)	0.0027 (8)
C14	0.0871 (18)	0.0854 (17)	0.0880 (17)	−0.0149 (14)	−0.0151 (14)	0.0390 (14)
C15	0.137 (3)	0.119 (3)	0.102 (2)	−0.004 (2)	−0.026 (2)	0.065 (2)
C16	0.136 (3)	0.093 (2)	0.0835 (19)	0.028 (2)	−0.0475 (19)	0.0104 (16)
C17	0.0658 (16)	0.0867 (18)	0.113 (2)	0.0183 (13)	−0.0335 (15)	−0.0249 (17)
C18	0.0580 (12)	0.0615 (12)	0.0798 (14)	0.0071 (10)	−0.0015 (10)	−0.0006 (11)
C19	0.0409 (9)	0.0603 (11)	0.0456 (9)	0.0028 (8)	−0.0032 (7)	−0.0083 (8)

S1—O1	1.4226 (15)	C8—C9	1.404 (4)
S1—O2	1.4356 (14)	C8—H8	0.9300
S1—N1	1.6090 (16)	C9—C10	1.337 (4)
S1—C1	1.766 (2)	C9—H9	0.9300
O3—C19	1.193 (2)	C10—H10	0.9300
O4—C19	1.314 (2)	C11—C12	1.529 (2)
O4—H1O	0.88 (3)	C11—C19	1.531 (2)
N1—C11	1.459 (2)	C11—H11	0.9800
N1—H1N	0.80 (2)	C12—C13	1.507 (2)
C1—C2	1.364 (3)	C12—H12A	0.9700
C1—C6	1.430 (3)	C12—H12B	0.9700
C2—C3	1.401 (4)	C13—C14	1.367 (3)
C2—H2	0.9300	C13—C18	1.372 (3)
C3—C4	1.350 (4)	C14—C15	1.376 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.405 (4)	C15—C16	1.340 (5)
C4—H4	0.9300	C15—H15	0.9300
C5—C10	1.408 (4)	C16—C17	1.364 (5)
C5—C6	1.427 (3)	C16—H16	0.9300
C6—C7	1.410 (3)	C17—C18	1.399 (3)
C7—C8	1.364 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—H18	0.9300
O1—S1—O2	118.96 (9)	C9—C10—C5	121.6 (2)
O1—S1—N1	107.60 (9)	C9—C10—H10	119.2
O2—S1—N1	105.70 (8)	C5—C10—H10	119.2
O1—S1—C1	110.58 (9)	N1—C11—C12	111.45 (15)
O2—S1—C1	106.34 (10)	N1—C11—C19	108.61 (14)
N1—S1—C1	107.01 (9)	C12—C11—C19	108.98 (14)
C19—O4—H1O	108.0 (16)	N1—C11—H11	109.3
C11—N1—S1	119.01 (12)	C12—C11—H11	109.3
C11—N1—H1N	120.3 (16)	C19—C11—H11	109.3
S1—N1—H1N	115.9 (16)	C13—C12—C11	112.56 (15)
C2—C1—C6	122.0 (2)	C13—C12—H12A	109.1
C2—C1—S1	116.37 (16)	C11—C12—H12A	109.1
C6—C1—S1	121.61 (15)	C13—C12—H12B	109.1
C1—C2—C3	119.8 (2)	C11—C12—H12B	109.1
C1—C2—H2	120.1	H12A—C12—H12B	107.8
C3—C2—H2	120.1	C14—C13—C18	118.6 (2)
C4—C3—C2	120.5 (3)	C14—C13—C12	120.2 (2)
C4—C3—H3	119.8	C18—C13—C12	121.15 (19)
C2—C3—H3	119.8	C13—C14—C15	120.8 (3)
C3—C4—C5	121.5 (3)	C13—C14—H14	119.6
C3—C4—H4	119.2	C15—C14—H14	119.6
C5—C4—H4	119.2	C16—C15—C14	120.8 (3)
C4—C5—C10	121.4 (2)	C16—C15—H15	119.6
C4—C5—C6	119.5 (2)	C14—C15—H15	119.6
C10—C5—C6	119.1 (2)	C15—C16—C17	119.8 (3)
C7—C6—C5	117.90 (19)	C15—C16—H16	120.1
C7—C6—C1	125.40 (18)	C17—C16—H16	120.1
C5—C6—C1	116.69 (19)	C16—C17—C18	120.0 (3)
C8—C7—C6	120.6 (2)	C16—C17—H17	120.0
C8—C7—H7	119.7	C18—C17—H17	120.0
C6—C7—H7	119.7	C13—C18—C17	119.9 (2)
C7—C8—C9	120.9 (3)	C13—C18—H18	120.0
C7—C8—H8	119.5	C17—C18—H18	120.0
C9—C8—H8	119.5	O3—C19—O4	124.08 (17)
C10—C9—C8	119.9 (2)	O3—C19—C11	124.07 (16)
C10—C9—H9	120.0	O4—C19—C11	111.81 (17)
C8—C9—H9	120.0
O1—S1—N1—C11	−168.97 (13)	C1—C6—C7—C8	178.1 (2)
O2—S1—N1—C11	−40.88 (15)	C6—C7—C8—C9	−0.1 (4)
C1—S1—N1—C11	72.17 (15)	C7—C8—C9—C10	1.0 (5)
O1—S1—C1—C2	141.61 (17)	C8—C9—C10—C5	−0.4 (5)
O2—S1—C1—C2	11.1 (2)	C4—C5—C10—C9	179.7 (3)
N1—S1—C1—C2	−101.49 (18)	C6—C5—C10—C9	−1.1 (4)
O1—S1—C1—C6	−41.01 (18)	S1—N1—C11—C12	−148.96 (13)
O2—S1—C1—C6	−171.48 (15)	S1—N1—C11—C19	90.98 (15)
N1—S1—C1—C6	75.89 (17)	N1—C11—C12—C13	62.6 (2)
C6—C1—C2—C3	−0.1 (4)	C19—C11—C12—C13	−177.57 (16)
S1—C1—C2—C3	177.2 (2)	C11—C12—C13—C14	70.3 (3)
C1—C2—C3—C4	1.5 (5)	C11—C12—C13—C18	−109.5 (2)
C2—C3—C4—C5	−1.3 (5)	C18—C13—C14—C15	1.0 (4)
C3—C4—C5—C10	178.9 (3)	C12—C13—C14—C15	−178.8 (3)
C3—C4—C5—C6	−0.3 (4)	C13—C14—C15—C16	−1.5 (6)
C4—C5—C6—C7	−178.9 (2)	C14—C15—C16—C17	1.0 (6)
C10—C5—C6—C7	1.9 (3)	C15—C16—C17—C18	−0.1 (5)
C4—C5—C6—C1	1.6 (3)	C14—C13—C18—C17	−0.1 (3)
C10—C5—C6—C1	−177.6 (2)	C12—C13—C18—C17	179.6 (2)
C2—C1—C6—C7	179.1 (2)	C16—C17—C18—C13	−0.3 (4)
S1—C1—C6—C7	1.9 (3)	N1—C11—C19—O3	47.5 (2)
C2—C1—C6—C5	−1.4 (3)	C12—C11—C19—O3	−74.1 (2)
S1—C1—C6—C5	−178.65 (15)	N1—C11—C19—O4	−134.51 (16)
C5—C6—C7—C8	−1.4 (3)	C12—C11—C19—O4	103.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O···O2ii	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O⋯O2ii	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)

Symmetry codes: (i) ; (ii) .