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The title compound, C12H15NO3S, exhibits antibacterial and antifungal activities. The cyclo­hexene ring exhibits disorder, indicating two possible conformations of the half-chair form. The molecular structure is approximately planar, supported by an intramolecular N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020987/ob6409sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020987/ob6409Isup2.hkl
Contains datablock I

CCDC reference: 251762

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.061
  • wR factor = 0.208
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
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 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Methyl 2-(acetylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate top
Crystal data top
C12H15NO3SF(000) = 1072
Mr = 253.32Dx = 1.357 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 710 reflections
a = 15.289 (14) Åθ = 1.6–26.4°
b = 10.644 (10) ŵ = 0.26 mm1
c = 15.790 (15) ÅT = 293 K
β = 105.212 (13)°Blocks, yellow
V = 2480 (4) Å30.39 × 0.30 × 0.20 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2519 independent reflections
Radiation source: fine-focus sealed tube1881 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1718
Tmin = 0.852, Tmax = 0.953k = 137
6489 measured reflectionsl = 1719
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.1396P)2 + 2.1364P]
where P = (Fo2 + 2Fc2)/3
2519 reflections(Δ/σ)max < 0.001
179 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.17 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*/UeqOcc. (<1)
S10.39866 (6)0.01021 (7)0.10400 (5)0.0578 (3)
O10.40002 (19)0.2571 (2)0.15491 (16)0.0738 (7)
O20.3527 (2)0.0444 (2)0.37569 (16)0.0760 (8)
O30.34647 (16)0.2486 (2)0.34375 (15)0.0635 (6)
N10.3788 (2)0.1184 (3)0.25484 (19)0.0602 (7)
C10.3820 (2)0.0090 (3)0.2078 (2)0.0499 (7)
C20.37110 (19)0.1105 (3)0.23693 (18)0.0482 (7)
C30.37689 (19)0.2047 (3)0.1726 (2)0.0497 (7)
C40.3679 (2)0.3439 (3)0.1795 (2)0.0613 (8)
C5A0.3544 (10)0.4112 (7)0.0909 (7)0.064 (2)0.58 (2)
C5B0.4086 (19)0.4104 (12)0.1125 (9)0.077 (5)0.42 (2)
C6A0.4263 (9)0.3623 (8)0.0459 (7)0.064 (2)0.58 (2)
C6B0.375 (2)0.3536 (13)0.0223 (10)0.085 (5)0.42 (2)
C70.4038 (3)0.2220 (3)0.0198 (2)0.0644 (9)
C80.3923 (2)0.1516 (3)0.09888 (19)0.0538 (7)
C90.3876 (2)0.2373 (3)0.2268 (2)0.0613 (8)
C100.3812 (3)0.3383 (3)0.2908 (3)0.0756 (10)
C110.3562 (2)0.1289 (3)0.3245 (2)0.0560 (8)
C120.3301 (3)0.2750 (4)0.4281 (2)0.0758 (11)
H1N0.367 (2)0.106 (4)0.304 (3)0.069 (11)*
H4A0.42200.37660.22040.074*
H4B0.31670.36220.20310.074*
H5A10.36090.50120.10000.076*0.58 (2)
H5A20.29400.39450.05400.076*0.58 (2)
H5B10.39260.49870.11010.093*0.42 (2)
H5B20.47410.40400.13120.093*0.42 (2)
H6A10.48640.36870.08580.077*0.58 (2)
H6A20.42500.41200.00590.077*0.58 (2)
H6B10.30910.35740.00460.102*0.42 (2)
H6B20.39730.40250.01930.102*0.42 (2)
H7A0.34850.21710.02730.077*
H7B0.45250.18490.00060.077*
H10A0.36870.41720.26070.113*
H10B0.33330.31860.31760.113*
H10C0.43760.34380.33530.113*
H12A0.27430.23610.43120.114*
H12B0.32600.36410.43540.114*
H12C0.37910.24210.47390.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0826 (6)0.0471 (5)0.0462 (5)0.0024 (4)0.0216 (4)0.0087 (3)
O10.1116 (19)0.0523 (14)0.0589 (15)0.0020 (12)0.0246 (13)0.0090 (11)
O20.125 (2)0.0555 (15)0.0610 (15)0.0014 (14)0.0477 (15)0.0009 (12)
O30.0889 (16)0.0551 (13)0.0544 (14)0.0060 (11)0.0330 (11)0.0088 (10)
N10.0871 (19)0.0463 (15)0.0492 (15)0.0025 (13)0.0212 (14)0.0036 (12)
C10.0561 (16)0.0474 (17)0.0463 (16)0.0036 (12)0.0134 (12)0.0055 (12)
C20.0534 (15)0.0474 (16)0.0463 (15)0.0014 (12)0.0174 (12)0.0038 (12)
C30.0540 (15)0.0456 (16)0.0512 (16)0.0051 (12)0.0170 (13)0.0058 (12)
C40.080 (2)0.0454 (17)0.064 (2)0.0035 (15)0.0269 (16)0.0068 (14)
C5A0.081 (6)0.043 (3)0.064 (5)0.001 (4)0.014 (4)0.001 (3)
C5B0.122 (13)0.053 (6)0.055 (6)0.015 (7)0.021 (7)0.018 (4)
C6A0.080 (5)0.056 (4)0.060 (5)0.010 (4)0.025 (4)0.005 (3)
C6B0.135 (15)0.064 (6)0.061 (8)0.015 (9)0.034 (9)0.005 (5)
C70.091 (2)0.055 (2)0.0499 (18)0.0081 (17)0.0239 (16)0.0038 (14)
C80.0639 (18)0.0512 (18)0.0469 (16)0.0077 (14)0.0155 (13)0.0070 (13)
C90.081 (2)0.0453 (18)0.055 (2)0.0013 (15)0.0134 (16)0.0064 (14)
C100.111 (3)0.0478 (19)0.072 (2)0.0027 (19)0.032 (2)0.0033 (17)
C110.0634 (18)0.0552 (18)0.0529 (17)0.0012 (14)0.0218 (14)0.0054 (14)
C120.096 (3)0.079 (3)0.061 (2)0.007 (2)0.037 (2)0.0149 (18)
Geometric parameters (Å, º) top
C5A—C41.537 (9)C3—C21.447 (4)
C5A—C6A1.548 (15)C7—H7A0.9700
C5A—H5A10.9700C7—H7B0.9700
C5A—H5A20.9700S1—C11.724 (3)
C6A—C71.564 (11)O3—C111.328 (4)
C6A—H6A10.9700O3—C121.446 (4)
C6A—H6A20.9700O2—C111.219 (4)
C5B—C6B1.51 (2)O1—C91.217 (4)
C5B—C41.534 (14)N1—C91.359 (4)
C5B—H5B10.9700N1—C11.389 (4)
C5B—H5B20.9700N1—H1N0.86 (4)
C6B—C71.473 (16)C11—C21.473 (4)
C6B—H6B10.9700C1—C21.377 (4)
C6B—H6B20.9700C9—C101.497 (5)
C4—C31.495 (4)C10—H10A0.9600
C4—H4A0.9700C10—H10B0.9600
C4—H4B0.9700C10—H10C0.9600
C8—C31.369 (4)C12—H12A0.9600
C8—C71.506 (4)C12—H12B0.9600
C8—S11.726 (4)C12—H12C0.9600
C4—C5A—C6A108.6 (9)C6B—C7—C8110.4 (6)
C4—C5A—H5A1110.0C8—C7—C6A108.8 (4)
C6A—C5A—H5A1110.0C6B—C7—H7A82.1
C4—C5A—H5A2110.0C8—C7—H7A109.9
C6A—C5A—H5A2110.0C6A—C7—H7A109.9
H5A1—C5A—H5A2108.3C6B—C7—H7B131.2
C5A—C6A—C7107.9 (9)C8—C7—H7B109.9
C5A—C6A—H6A1110.1C6A—C7—H7B109.9
C7—C6A—H6A1110.1H7A—C7—H7B108.3
C5A—C6A—H6A2110.1C1—S1—C890.95 (14)
C7—C6A—H6A2110.1C11—O3—C12116.9 (3)
H6A1—C6A—H6A2108.4C9—N1—C1125.8 (3)
C6B—C5B—C4111.5 (16)C9—N1—H1N120 (3)
C6B—C5B—H5B1109.3C1—N1—H1N114 (3)
C4—C5B—H5B1109.3O2—C11—O3122.0 (3)
C6B—C5B—H5B2109.3O2—C11—C2124.6 (3)
C4—C5B—H5B2109.3O3—C11—C2113.4 (3)
H5B1—C5B—H5B2108.0C2—C1—N1124.8 (3)
C7—C6B—C5B112.0 (18)C2—C1—S1112.7 (2)
C7—C6B—H6B1109.2N1—C1—S1122.5 (2)
C5B—C6B—H6B1109.2C1—C2—C3111.8 (3)
C7—C6B—H6B2109.2C1—C2—C11119.9 (3)
C5B—C6B—H6B2109.2C3—C2—C11128.3 (3)
H6B1—C6B—H6B2107.9O1—C9—N1121.3 (3)
C3—C4—C5B110.2 (6)O1—C9—C10124.0 (3)
C3—C4—C5A112.8 (4)N1—C9—C10114.7 (3)
C3—C4—H4A109.0C9—C10—H10A109.5
C5B—C4—H4A82.2C9—C10—H10B109.5
C5A—C4—H4A109.0H10A—C10—H10B109.5
C3—C4—H4B109.0C9—C10—H10C109.5
C5B—C4—H4B133.3H10A—C10—H10C109.5
C5A—C4—H4B109.0H10B—C10—H10C109.5
H4A—C4—H4B107.8O3—C12—H12A109.5
C3—C8—C7125.7 (3)O3—C12—H12B109.5
C3—C8—S1113.1 (2)H12A—C12—H12B109.5
C7—C8—S1121.2 (2)O3—C12—H12C109.5
C8—C3—C2111.5 (3)H12A—C12—H12C109.5
C8—C3—C4120.8 (3)H12B—C12—H12C109.5
C2—C3—C4127.7 (3)
C4—C5A—C6A—C768.2 (14)C3—C8—S1—C10.8 (2)
C4—C5B—C6B—C764 (3)C7—C8—S1—C1178.7 (3)
C6B—C5B—C4—C349 (3)C12—O3—C11—O20.9 (5)
C6B—C5B—C4—C5A52.4 (18)C12—O3—C11—C2179.1 (3)
C6A—C5A—C4—C348.3 (13)C9—N1—C1—C2178.7 (3)
C6A—C5A—C4—C5B43.0 (11)C9—N1—C1—S10.2 (5)
C7—C8—C3—C2178.7 (3)C8—S1—C1—C20.6 (2)
S1—C8—C3—C20.8 (3)C8—S1—C1—N1179.6 (3)
C7—C8—C3—C41.4 (5)N1—C1—C2—C3179.2 (3)
S1—C8—C3—C4179.1 (2)S1—C1—C2—C30.3 (3)
C5B—C4—C3—C818.7 (11)N1—C1—C2—C111.0 (5)
C5A—C4—C3—C814.1 (7)S1—C1—C2—C11180.0 (2)
C5B—C4—C3—C2161.5 (11)C8—C3—C2—C10.3 (4)
C5A—C4—C3—C2165.8 (6)C4—C3—C2—C1179.5 (3)
C5B—C6B—C7—C844 (3)C8—C3—C2—C11179.4 (3)
C5B—C6B—C7—C6A49 (2)C4—C3—C2—C110.8 (5)
C3—C8—C7—C6B13.7 (13)O2—C11—C2—C10.2 (5)
S1—C8—C7—C6B166.9 (12)O3—C11—C2—C1179.8 (3)
C3—C8—C7—C6A17.9 (7)O2—C11—C2—C3179.5 (3)
S1—C8—C7—C6A161.6 (5)O3—C11—C2—C30.6 (4)
C5A—C6A—C7—C6B47.3 (13)C1—N1—C9—O10.3 (5)
C5A—C6A—C7—C851.2 (11)C1—N1—C9—C10179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.83 (4)2.01 (4)2.683 (5)138 (4)
 

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