1-[(2-Naphthyl­sulfon­yl)­oxy]pyrrolidine-2,5-dione

The title compound, C₁₄H₁₁NO₅S, is an ester of β-naphthyl­sulfonic acid and N-hydroxy­succinimide. The N atom retains a flattened pyramidal geometry. The C atoms of the succinic ring are coplanar and the N atom is slightly displaced from their plane, leading to a pseudo-envelope conformation. The crystal structure is stabilized by a three-dimensional network of weak C—H...O and offset π-stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.133
• Data-to-parameter ratio = 30.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C14H11NO5S	F(000) = 632
Mr = 305.31	Dx = 1.542 Mg m^−3
Monoclinic, P21/c	Melting point: 438 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.090 (3) Å	Cell parameters from 14458 reflections
b = 13.403 (3) Å	θ = 4.7–38.0°
c = 8.157 (3) Å	µ = 0.27 mm^−1
β = 95.79 (3)°	T = 100 K
V = 1315.0 (7) Å^3	Needle, colourless
Z = 4	0.45 × 0.3 × 0.2 mm

Data collection

Oxford Xcalibur PX κ geometry diffractometer	7118 independent reflections
Radiation source: fine-focus sealed tube	5112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω and φ scans	θmax = 38.0°, θmin = 4.7°
Absorption correction: numerical (CrysAlisRED; Oxford Diffraction, 2003)	h = −20→20
Tmin = 0.896, Tmax = 0.952	k = −23→21
29699 measured reflections	l = −14→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0771P)^2] where P = (Fo^2 + 2Fc^2)/3
7118 reflections	(Δ/σ)max = 0.001
234 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
S	0.23120 (2)	0.59933 (2)	0.75175 (3)	0.01642 (6)
O1	0.20375 (6)	0.69769 (5)	0.86448 (8)	0.01888 (14)
O2	0.21382 (6)	0.51784 (6)	0.85946 (9)	0.02159 (15)
O3	0.16787 (6)	0.60825 (6)	0.59480 (9)	0.02202 (15)
O4	−0.02421 (7)	0.70498 (7)	0.86779 (11)	0.03093 (19)
O5	0.27899 (6)	0.87104 (6)	0.71687 (10)	0.02390 (16)
N	0.13668 (6)	0.76980 (6)	0.78390 (10)	0.01723 (15)
C1	0.41150 (8)	0.62424 (7)	0.58730 (12)	0.01840 (17)
H1	0.3598 (14)	0.6266 (11)	0.486 (2)	0.033 (4)*
C2	0.37315 (8)	0.61330 (7)	0.73870 (12)	0.01584 (16)
C3	0.44489 (8)	0.60716 (8)	0.88701 (13)	0.01951 (17)
H3	0.4177 (14)	0.5988 (11)	0.990 (2)	0.031 (4)*
C4	0.55745 (9)	0.61280 (8)	0.87766 (13)	0.02264 (19)
H4	0.6138 (15)	0.6116 (12)	0.976 (2)	0.038 (4)*
C5	0.71765 (9)	0.63250 (9)	0.71254 (16)	0.0265 (2)
H5	0.7673 (15)	0.6314 (13)	0.812 (2)	0.041 (4)*
C6	0.75743 (10)	0.64339 (9)	0.56225 (16)	0.0284 (2)
H6	0.8382 (15)	0.6544 (13)	0.557 (2)	0.047 (5)*
C7	0.68468 (10)	0.64560 (8)	0.41618 (15)	0.0277 (2)
H7	0.7116 (13)	0.6550 (12)	0.309 (2)	0.035 (4)*
C8	0.57178 (10)	0.63901 (9)	0.42288 (14)	0.0251 (2)
H8	0.5215 (14)	0.6435 (12)	0.329 (2)	0.036 (4)*
C9	0.52785 (8)	0.62908 (7)	0.57647 (12)	0.01839 (17)
C10	0.60144 (8)	0.62430 (7)	0.72389 (13)	0.01913 (17)
C11	0.02414 (8)	0.77184 (8)	0.80660 (12)	0.02063 (18)
C12	−0.01831 (9)	0.87119 (9)	0.74091 (14)	0.0241 (2)
H12A	−0.0519 (14)	0.9105 (12)	0.8242 (19)	0.032 (4)*
H12B	−0.0780 (13)	0.8570 (11)	0.6527 (18)	0.028 (4)*
C13	0.08309 (9)	0.92642 (8)	0.68588 (13)	0.02246 (19)
H13A	0.0800 (12)	0.9397 (11)	0.5701 (18)	0.027 (4)*
H13B	0.1004 (14)	0.9876 (13)	0.741 (2)	0.036 (4)*
C14	0.18143 (8)	0.85829 (7)	0.72745 (11)	0.01784 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01350 (11)	0.01930 (11)	0.01649 (11)	−0.00019 (7)	0.00164 (7)	−0.00044 (7)
O1	0.0180 (3)	0.0224 (3)	0.0158 (3)	0.0076 (2)	−0.0008 (2)	0.0002 (2)
O2	0.0208 (3)	0.0208 (3)	0.0239 (3)	−0.0028 (3)	0.0056 (3)	0.0014 (3)
O3	0.0170 (3)	0.0310 (4)	0.0175 (3)	0.0008 (3)	−0.0012 (2)	−0.0032 (3)
O4	0.0191 (4)	0.0358 (4)	0.0382 (5)	−0.0021 (3)	0.0044 (3)	0.0125 (4)
O5	0.0183 (3)	0.0328 (4)	0.0207 (3)	−0.0049 (3)	0.0028 (3)	−0.0012 (3)
N	0.0133 (3)	0.0195 (3)	0.0188 (4)	0.0030 (3)	0.0011 (3)	0.0018 (3)
C1	0.0170 (4)	0.0212 (4)	0.0173 (4)	0.0018 (3)	0.0030 (3)	0.0013 (3)
C2	0.0142 (4)	0.0165 (4)	0.0171 (4)	0.0015 (3)	0.0026 (3)	0.0015 (3)
C3	0.0163 (4)	0.0246 (4)	0.0175 (4)	0.0009 (3)	0.0016 (3)	0.0036 (3)
C4	0.0155 (4)	0.0311 (5)	0.0210 (4)	0.0008 (4)	0.0003 (3)	0.0030 (4)
C5	0.0168 (4)	0.0294 (5)	0.0340 (6)	0.0009 (4)	0.0061 (4)	−0.0009 (4)
C6	0.0198 (5)	0.0251 (5)	0.0428 (7)	0.0011 (4)	0.0145 (4)	−0.0012 (4)
C7	0.0287 (5)	0.0239 (5)	0.0335 (6)	0.0011 (4)	0.0180 (4)	0.0000 (4)
C8	0.0256 (5)	0.0272 (5)	0.0242 (5)	0.0009 (4)	0.0102 (4)	0.0000 (4)
C9	0.0188 (4)	0.0164 (4)	0.0208 (4)	0.0011 (3)	0.0063 (3)	0.0008 (3)
C10	0.0154 (4)	0.0177 (4)	0.0249 (5)	0.0015 (3)	0.0048 (3)	0.0011 (3)
C11	0.0142 (4)	0.0266 (5)	0.0212 (4)	0.0019 (3)	0.0023 (3)	0.0019 (3)
C12	0.0190 (4)	0.0286 (5)	0.0253 (5)	0.0072 (4)	0.0049 (4)	0.0052 (4)
C13	0.0246 (5)	0.0207 (4)	0.0227 (5)	0.0034 (4)	0.0053 (4)	0.0023 (3)
C14	0.0185 (4)	0.0215 (4)	0.0136 (4)	−0.0004 (3)	0.0025 (3)	−0.0014 (3)

Geometric parameters (Å, º)

S—O3	1.4289 (10)	C5—C6	1.3691 (18)
S—O2	1.4305 (8)	C5—C10	1.4216 (15)
S—O1	1.6599 (8)	C5—H5	0.959 (19)
S—C2	1.7402 (10)	C6—C7	1.4081 (19)
O1—N	1.3842 (11)	C6—H6	0.993 (18)
O4—C11	1.2053 (13)	C7—C8	1.3744 (17)
O5—C14	1.2034 (13)	C7—H7	0.970 (16)
N—C11	1.3918 (13)	C8—C9	1.4155 (15)
N—C14	1.4006 (13)	C8—H8	0.933 (17)
C1—C2	1.3701 (15)	C9—C10	1.4233 (16)
C1—C9	1.4198 (14)	C11—C12	1.5060 (15)
C1—H1	0.987 (17)	C12—C13	1.5373 (17)
C2—C3	1.4180 (15)	C12—H12A	0.980 (16)
C3—C4	1.3727 (15)	C12—H12B	0.985 (15)
C3—H3	0.940 (16)	C13—C14	1.5103 (15)
C4—C10	1.4194 (16)	C13—H13A	0.958 (15)
C4—H4	0.998 (18)	C13—H13B	0.948 (17)
O3—S—O2	121.03 (5)	C8—C7—H7	118.0 (9)
O3—S—O1	108.11 (4)	C6—C7—H7	121.7 (9)
O2—S—O1	102.49 (5)	C7—C8—C9	120.26 (11)
O3—S—C2	112.26 (5)	C7—C8—H8	122.0 (10)
O2—S—C2	109.06 (5)	C9—C8—H8	117.7 (10)
O1—S—C2	101.65 (4)	C8—C9—C1	121.46 (10)
N—O1—S	115.58 (6)	C8—C9—C10	119.58 (10)
O1—N—C11	118.97 (8)	C1—C9—C10	118.96 (9)
O1—N—C14	121.34 (8)	C4—C10—C5	121.80 (10)
C11—N—C14	116.25 (8)	C4—C10—C9	119.57 (9)
C2—C1—C9	119.24 (10)	C5—C10—C9	118.63 (10)
C2—C1—H1	121.2 (10)	O4—C11—N	124.19 (10)
C9—C1—H1	119.6 (10)	O4—C11—C12	129.99 (9)
C1—C2—C3	122.80 (9)	N—C11—C12	105.83 (8)
C1—C2—S	119.48 (8)	C11—C12—C13	106.05 (9)
C3—C2—S	117.62 (8)	C11—C12—H12A	112.3 (9)
C4—C3—C2	118.29 (10)	C13—C12—H12A	110.0 (10)
C4—C3—H3	119.6 (10)	C11—C12—H12B	106.7 (9)
C2—C3—H3	122.1 (10)	C13—C12—H12B	115.3 (9)
C3—C4—C10	121.13 (10)	H12A—C12—H12B	106.6 (12)
C3—C4—H4	123.7 (10)	C14—C13—C12	106.04 (9)
C10—C4—H4	115.2 (10)	C14—C13—H13A	106.6 (9)
C6—C5—C10	120.35 (12)	C12—C13—H13A	115.1 (9)
C6—C5—H5	120.8 (11)	C14—C13—H13B	106.6 (10)
C10—C5—H5	118.8 (11)	C12—C13—H13B	115.0 (10)
C5—C6—C7	120.93 (11)	H13A—C13—H13B	107.0 (13)
C5—C6—H6	119.1 (10)	O5—C14—N	123.90 (9)
C7—C6—H6	119.8 (10)	O5—C14—C13	130.78 (9)
C8—C7—C6	120.21 (11)	N—C14—C13	105.33 (8)
O3—S—O1—N	−5.49 (8)	C2—C1—C9—C10	−1.17 (14)
O2—S—O1—N	−134.39 (7)	C3—C4—C10—C5	178.56 (10)
C2—S—O1—N	112.83 (7)	C3—C4—C10—C9	−0.64 (15)
S—O1—N—C11	99.70 (9)	C6—C5—C10—C4	179.91 (11)
S—O1—N—C14	−102.01 (9)	C6—C5—C10—C9	−0.88 (16)
C9—C1—C2—C3	0.43 (14)	C8—C9—C10—C4	−179.03 (10)
C9—C1—C2—S	−175.92 (7)	C1—C9—C10—C4	1.28 (14)
O3—S—C2—C1	−4.19 (9)	C8—C9—C10—C5	1.73 (14)
O2—S—C2—C1	132.76 (8)	C1—C9—C10—C5	−177.95 (9)
O1—S—C2—C1	−119.49 (8)	O1—N—C11—O4	−13.90 (15)
O3—S—C2—C3	179.27 (7)	C14—N—C11—O4	−173.27 (10)
O2—S—C2—C3	−43.78 (9)	O1—N—C11—C12	165.93 (8)
O1—S—C2—C3	63.97 (8)	C14—N—C11—C12	6.56 (11)
C1—C2—C3—C4	0.22 (15)	O4—C11—C12—C13	177.45 (11)
S—C2—C3—C4	176.64 (8)	N—C11—C12—C13	−2.36 (11)
C2—C3—C4—C10	−0.11 (15)	C11—C12—C13—C14	−1.96 (11)
C10—C5—C6—C7	−0.70 (17)	O1—N—C14—O5	13.85 (14)
C5—C6—C7—C8	1.44 (18)	C11—N—C14—O5	172.69 (9)
C6—C7—C8—C9	−0.55 (17)	O1—N—C14—C13	−166.65 (8)
C7—C8—C9—C1	178.64 (10)	C11—N—C14—C13	−7.80 (11)
C7—C8—C9—C10	−1.03 (15)	C12—C13—C14—O5	−175.03 (10)
C2—C1—C9—C8	179.15 (9)	C12—C13—C14—N	5.51 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5^i	0.98 (2)	2.31 (2)	3.275 (2)	165.8 (14)
C13—H13A···O2^i	0.96 (2)	2.54 (2)	3.316 (2)	138.0 (12)

Symmetry code: (i) x, −y+3/2, z−1/2.