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The solid-state conformation of the title compound, C15H15NO4S, has been established by X-ray crystallography. The orientation of the sulfonyl moiety is defined by the C—S—N—C torsion angle of −108.24 (16)°. The angle between the naphthyl ring and the direction of the S—N bond is 71.24 (18)°. The dioxepinoaziridine moiety system a boat–chair (BC) conformation. The crystal packing is defined by optimized π–π inter­actions between parallel naphthyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024931/wk6058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024931/wk6058Isup2.hkl
Contains datablock I

CCDC reference: 283999

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.128
  • Data-to-parameter ratio = 21.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.70 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

1-(1-Naphthylsulfonyl)-1a,2,6,6a-tetrahydro-1H,4H-1,3-dioxepino[5,6-b]azirine top
Crystal data top
C15H15NO4SF(000) = 640
Mr = 305.34Dx = 1.436 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32 reflections
a = 10.2540 (7) Åθ = 12.3–17.8°
b = 17.0933 (9) ŵ = 0.25 mm1
c = 8.0635 (11) ÅT = 295 K
β = 92.560 (6)°Prism, colorless
V = 1411.9 (2) Å30.4 × 0.3 × 0.2 mm
Z = 4
Data collection top
Philips PW1100 updated by Stoe
diffractometer
Rint = 0.060
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 2.4°
Graphite monochromatorh = 014
ω–2θ scansk = 240
4327 measured reflectionsl = 1111
4125 independent reflections3 standard reflections every 120 min
1880 reflections with I > 2σ(I) intensity decay: 3.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0558P)2]
where P = (Fo2 + 2Fc2)/3
4125 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.17508 (6)0.96287 (3)0.22937 (7)0.03418 (16)
N10.12014 (17)0.87384 (10)0.1825 (2)0.0323 (4)
O10.06486 (16)1.00540 (10)0.2843 (2)0.0501 (5)
O20.24531 (16)0.99663 (9)0.09783 (19)0.0476 (4)
O30.09667 (17)0.75906 (10)0.1355 (2)0.0514 (5)
O50.11073 (18)0.70397 (9)0.1424 (2)0.0501 (5)
C1A0.0325 (2)0.86906 (13)0.0294 (3)0.0375 (5)
H11A0.02660.91840.03240.045*
C20.0960 (2)0.82847 (14)0.0402 (3)0.0487 (6)
H2A0.15720.86490.08620.058*
H2B0.12810.81600.07170.058*
C40.0171 (3)0.69851 (14)0.0774 (3)0.0529 (7)
H4A0.05340.64840.10790.063*
H4B0.01690.70080.04280.063*
C6A0.1631 (2)0.83335 (12)0.0299 (3)0.0366 (5)
H6A0.22620.86330.03220.044*
C60.1945 (2)0.74783 (13)0.0443 (3)0.0464 (6)
H6B0.19230.72550.06640.056*
H6C0.28300.74240.09070.056*
C70.2826 (2)0.94397 (12)0.4020 (3)0.0341 (5)
C80.2435 (2)0.96960 (14)0.5526 (3)0.0428 (6)
H80.16320.99430.56110.051*
C90.3268 (3)0.95809 (16)0.6958 (3)0.0582 (8)
H90.30200.97660.79820.070*
C100.4417 (3)0.92040 (17)0.6844 (3)0.0599 (8)
H100.49450.91300.77990.072*
C110.4836 (3)0.89221 (14)0.5333 (3)0.0488 (7)
C120.4051 (2)0.90491 (12)0.3843 (3)0.0387 (5)
C130.4523 (2)0.87768 (14)0.2331 (3)0.0478 (6)
H130.40390.88670.13470.057*
C140.5675 (3)0.83840 (17)0.2288 (4)0.0675 (8)
H140.59540.82020.12770.081*
C150.6444 (3)0.82492 (18)0.3724 (5)0.0758 (10)
H150.72290.79810.36730.091*
C160.6038 (3)0.85126 (17)0.5195 (5)0.0694 (9)
H160.65600.84240.61500.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0430 (3)0.0253 (2)0.0340 (3)0.0034 (3)0.0006 (2)0.0010 (2)
N10.0377 (10)0.0283 (9)0.0303 (10)0.0026 (8)0.0033 (8)0.0013 (7)
O10.0521 (10)0.0404 (9)0.0576 (11)0.0158 (8)0.0012 (9)0.0093 (8)
O20.0652 (11)0.0382 (9)0.0393 (9)0.0066 (9)0.0039 (8)0.0062 (8)
O30.0612 (11)0.0432 (10)0.0499 (11)0.0063 (9)0.0036 (9)0.0010 (8)
O50.0724 (12)0.0332 (9)0.0436 (10)0.0049 (9)0.0107 (9)0.0039 (7)
C1A0.0494 (15)0.0297 (11)0.0326 (12)0.0044 (10)0.0082 (11)0.0021 (9)
C20.0485 (15)0.0438 (14)0.0526 (15)0.0004 (12)0.0129 (12)0.0028 (12)
C40.0704 (19)0.0337 (13)0.0536 (16)0.0091 (13)0.0074 (14)0.0016 (12)
C6A0.0477 (13)0.0328 (11)0.0288 (11)0.0017 (11)0.0020 (10)0.0040 (10)
C60.0548 (15)0.0362 (12)0.0477 (14)0.0106 (12)0.0054 (12)0.0118 (11)
C70.0396 (12)0.0296 (11)0.0329 (11)0.0055 (10)0.0003 (10)0.0000 (9)
C80.0501 (14)0.0423 (13)0.0366 (13)0.0123 (12)0.0071 (11)0.0056 (11)
C90.083 (2)0.0612 (17)0.0307 (13)0.0336 (17)0.0061 (13)0.0037 (13)
C100.068 (2)0.0631 (18)0.0463 (16)0.0239 (16)0.0187 (14)0.0182 (14)
C110.0514 (16)0.0385 (13)0.0550 (16)0.0133 (12)0.0130 (13)0.0111 (12)
C120.0398 (13)0.0273 (11)0.0485 (14)0.0076 (10)0.0041 (11)0.0027 (10)
C130.0405 (14)0.0460 (15)0.0566 (16)0.0026 (12)0.0008 (12)0.0119 (12)
C140.0462 (17)0.0604 (18)0.096 (2)0.0046 (14)0.0041 (16)0.0251 (17)
C150.0512 (19)0.0547 (19)0.121 (3)0.0108 (15)0.007 (2)0.0016 (19)
C160.0496 (18)0.0526 (17)0.103 (3)0.0072 (15)0.0283 (17)0.0237 (18)
Geometric parameters (Å, º) top
S1—O21.4300 (16)C6—H6C0.9700
S1—O11.4305 (16)C7—C81.368 (3)
S1—N11.6604 (18)C7—C121.435 (3)
S1—C71.766 (2)C8—C91.418 (3)
N1—C6A1.496 (3)C8—H80.9300
N1—C1A1.496 (3)C9—C101.350 (4)
O3—C41.411 (3)C9—H90.9300
O3—C21.414 (3)C10—C111.396 (4)
O5—C41.393 (3)C10—H100.9300
O5—C61.409 (3)C11—C161.425 (4)
C1A—C6A1.471 (3)C11—C121.433 (3)
C1A—C21.495 (3)C12—C131.410 (3)
C1A—H11A0.9800C13—C141.360 (4)
C2—H2A0.9700C13—H130.9300
C2—H2B0.9700C14—C151.390 (4)
C4—H4A0.9700C14—H140.9300
C4—H4B0.9700C15—C161.352 (4)
C6A—C61.500 (3)C15—H150.9300
C6A—H6A0.9800C16—H160.9300
C6—H6B0.9700
O2—S1—O1117.09 (10)O5—C6—H6B108.4
O2—S1—N1112.22 (9)C6A—C6—H6B108.4
O1—S1—N1105.75 (10)O5—C6—H6C108.4
O2—S1—C7109.95 (10)C6A—C6—H6C108.4
O1—S1—C7108.84 (10)H6B—C6—H6C107.5
N1—S1—C7101.83 (9)C8—C7—C12122.0 (2)
C6A—N1—C1A58.90 (13)C8—C7—S1116.37 (18)
C6A—N1—S1120.13 (14)C12—C7—S1121.65 (17)
C1A—N1—S1115.01 (13)C7—C8—C9119.3 (2)
C4—O3—C2114.70 (19)C7—C8—H8120.4
C4—O5—C6114.30 (19)C9—C8—H8120.4
C6A—C1A—C2127.7 (2)C10—C9—C8120.4 (2)
C6A—C1A—N160.52 (13)C10—C9—H9119.8
C2—C1A—N1118.40 (18)C8—C9—H9119.8
C6A—C1A—H11A113.2C9—C10—C11121.9 (2)
C2—C1A—H11A113.2C9—C10—H10119.1
N1—C1A—H11A113.2C11—C10—H10119.1
O3—C2—C1A116.5 (2)C10—C11—C16122.6 (3)
O3—C2—H2A108.2C10—C11—C12119.7 (3)
C1A—C2—H2A108.2C16—C11—C12117.7 (3)
O3—C2—H2B108.2C13—C12—C11118.2 (2)
C1A—C2—H2B108.2C13—C12—C7125.1 (2)
H2A—C2—H2B107.3C11—C12—C7116.7 (2)
O5—C4—O3112.0 (2)C14—C13—C12121.1 (3)
O5—C4—H4A109.2C14—C13—H13119.4
O3—C4—H4A109.2C12—C13—H13119.4
O5—C4—H4B109.2C13—C14—C15121.4 (3)
O3—C4—H4B109.2C13—C14—H14119.3
H4A—C4—H4B107.9C15—C14—H14119.3
C1A—C6A—N160.58 (13)C16—C15—C14119.4 (3)
C1A—C6A—C6126.6 (2)C16—C15—H15120.3
N1—C6A—C6117.20 (19)C14—C15—H15120.3
C1A—C6A—H6A113.8C15—C16—C11122.2 (3)
N1—C6A—H6A113.8C15—C16—H16118.9
C6—C6A—H6A113.8C11—C16—H16118.9
O5—C6—C6A115.3 (2)
O2—S1—N1—C6A9.29 (18)N1—S1—C7—C8109.63 (18)
O1—S1—N1—C6A138.07 (15)O2—S1—C7—C1247.83 (19)
C7—S1—N1—C6A108.24 (16)O1—S1—C7—C12177.31 (17)
O2—S1—N1—C1A57.87 (17)N1—S1—C7—C1271.32 (19)
O1—S1—N1—C1A70.92 (16)C12—C7—C8—C90.6 (3)
C7—S1—N1—C1A175.39 (15)S1—C7—C8—C9178.40 (17)
S1—N1—C1A—C6A111.43 (16)C7—C8—C9—C101.8 (4)
C6A—N1—C1A—C2119.5 (2)C8—C9—C10—C110.6 (4)
S1—N1—C1A—C2129.03 (18)C9—C10—C11—C16179.0 (2)
C4—O3—C2—C1A61.3 (3)C9—C10—C11—C121.6 (4)
C6A—C1A—C2—O332.6 (3)C10—C11—C12—C13178.1 (2)
N1—C1A—C2—O340.6 (3)C16—C11—C12—C131.3 (3)
C6—O5—C4—O391.2 (2)C10—C11—C12—C72.6 (3)
C2—O3—C4—O587.6 (2)C16—C11—C12—C7178.0 (2)
C2—C1A—C6A—N1104.7 (2)C8—C7—C12—C13179.3 (2)
C2—C1A—C6A—C61.1 (4)S1—C7—C12—C130.3 (3)
N1—C1A—C6A—C6103.6 (2)C8—C7—C12—C111.5 (3)
S1—N1—C6A—C1A102.75 (17)S1—C7—C12—C11179.49 (16)
C1A—N1—C6A—C6118.7 (2)C11—C12—C13—C141.9 (4)
S1—N1—C6A—C6138.52 (19)C7—C12—C13—C14177.3 (2)
C4—O5—C6—C6A66.0 (3)C12—C13—C14—C151.3 (4)
C1A—C6A—C6—O532.7 (3)C13—C14—C15—C160.1 (5)
N1—C6A—C6—O539.5 (3)C14—C15—C16—C110.5 (5)
O2—S1—C7—C8131.22 (18)C10—C11—C16—C15179.2 (3)
O1—S1—C7—C81.7 (2)C12—C11—C16—C150.1 (4)
 

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