The title compound, C
14H
11NO
5S, 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.
Supporting information
CCDC reference: 271860
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.133
- Data-to-parameter ratio = 30.4
checkCIF/PLATON results
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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.
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.45 × 0.3 × 0.2 mm |
Data collection top
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 top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5i | 0.98 (2) | 2.31 (2) | 3.275 (2) | 165.8 (14) |
C13—H13A···O2i | 0.96 (2) | 2.54 (2) | 3.316 (2) | 138.0 (12) |
Symmetry code: (i) x, −y+3/2, z−1/2. |