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The title compound, C13H15NO2S2, the morpholine ring adopts the usual chair conformation and the four C atoms deviate only slightly from coplanarity. The crystal structure is stabilized by some weak intramolecular C—H...S hydrogen-bond interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033999/wn6317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033999/wn6317Isup2.hkl
Contains datablock I

CCDC reference: 263656

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.027
  • wR factor = 0.096
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-Oxo-2-phenylethyl morpholine-4-carbodithioate top
Crystal data top
C13H15NO2S2F(000) = 1184
Mr = 281.38Dx = 1.386 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2566 reflections
a = 9.5294 (9) Åθ = 2.4–20.1°
b = 8.4805 (8) ŵ = 0.39 mm1
c = 33.362 (3) ÅT = 293 K
V = 2696.1 (4) Å3Block, colorless
Z = 80.54 × 0.34 × 0.18 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2367 independent reflections
Radiation source: fine-focus sealed tube1349 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 117
Tmin = 0.801, Tmax = 0.933k = 109
13423 measured reflectionsl = 3839
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0531P)2]
where P = (Fo2 + 2Fc2)/3
2367 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 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
S10.57422 (8)1.10672 (9)0.35357 (2)0.0678 (3)
S20.35387 (8)1.02771 (8)0.41461 (2)0.0590 (2)
N10.5458 (2)1.2449 (2)0.42437 (6)0.0505 (5)
O10.69414 (19)1.3915 (2)0.48758 (5)0.0632 (5)
O20.4933 (2)0.7222 (2)0.39559 (5)0.0667 (5)
C10.5011 (3)1.1378 (3)0.39780 (7)0.0460 (6)
C20.6645 (3)1.3496 (3)0.41651 (7)0.0566 (7)
H2A0.63101.45620.41210.068*
H2B0.71341.31540.39250.068*
C30.7626 (3)1.3469 (3)0.45140 (7)0.0592 (7)
H3A0.80091.24160.45440.071*
H3B0.83991.41850.44630.071*
C40.5852 (3)1.2832 (3)0.49581 (8)0.0663 (8)
H4A0.54001.31180.52080.080*
H4B0.62471.17850.49900.080*
C50.4776 (3)1.2805 (3)0.46287 (8)0.0650 (8)
H5A0.40711.20110.46870.078*
H5B0.43121.38210.46130.078*
C60.3215 (3)0.9038 (3)0.37217 (8)0.0568 (7)
H6A0.22620.86420.37390.068*
H6B0.32800.96750.34810.068*
C70.4202 (3)0.7650 (3)0.36808 (8)0.0495 (7)
C80.4194 (3)0.6798 (3)0.32903 (7)0.0489 (7)
C90.5168 (3)0.5621 (3)0.32268 (9)0.0679 (8)
H90.58240.53970.34250.082*
C100.5186 (4)0.4775 (4)0.28767 (10)0.0844 (10)
H100.58440.39780.28400.101*
C110.4235 (5)0.5105 (4)0.25815 (10)0.0870 (11)
H110.42540.45410.23420.104*
C120.3266 (4)0.6251 (4)0.26368 (10)0.0875 (11)
H120.26210.64700.24350.105*
C130.3223 (3)0.7108 (3)0.29932 (9)0.0685 (8)
H130.25450.78830.30310.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0807 (6)0.0779 (5)0.0446 (4)0.0142 (4)0.0076 (4)0.0054 (4)
S20.0511 (4)0.0578 (4)0.0680 (5)0.0040 (4)0.0059 (4)0.0016 (4)
N10.0476 (13)0.0579 (13)0.0461 (13)0.0058 (11)0.0054 (10)0.0042 (11)
O10.0635 (12)0.0752 (12)0.0507 (11)0.0118 (11)0.0021 (10)0.0103 (9)
O20.0736 (13)0.0661 (12)0.0605 (12)0.0140 (10)0.0214 (11)0.0011 (10)
C10.0447 (15)0.0456 (13)0.0477 (15)0.0064 (12)0.0047 (12)0.0047 (12)
C20.0633 (19)0.0564 (16)0.0500 (16)0.0121 (15)0.0036 (14)0.0032 (12)
C30.0549 (18)0.0684 (18)0.0543 (16)0.0111 (14)0.0042 (15)0.0007 (14)
C40.072 (2)0.079 (2)0.0482 (17)0.0079 (18)0.0132 (15)0.0072 (15)
C50.0547 (18)0.078 (2)0.0622 (19)0.0038 (16)0.0127 (15)0.0172 (15)
C60.0483 (17)0.0519 (15)0.0702 (18)0.0050 (14)0.0125 (14)0.0022 (13)
C70.0438 (15)0.0473 (15)0.0574 (17)0.0035 (13)0.0067 (14)0.0118 (13)
C80.0516 (16)0.0464 (15)0.0488 (16)0.0076 (13)0.0047 (14)0.0096 (12)
C90.072 (2)0.077 (2)0.0547 (19)0.0046 (18)0.0018 (16)0.0070 (16)
C100.101 (3)0.085 (2)0.067 (2)0.005 (2)0.017 (2)0.0037 (19)
C110.129 (3)0.075 (2)0.057 (2)0.030 (2)0.009 (2)0.0003 (18)
C120.114 (3)0.080 (2)0.068 (2)0.028 (2)0.037 (2)0.0129 (19)
C130.081 (2)0.0547 (17)0.070 (2)0.0104 (16)0.0235 (17)0.0084 (15)
Geometric parameters (Å, º) top
S1—C11.653 (3)C5—H5A0.9700
S2—C11.776 (3)C5—H5B0.9700
S2—C61.790 (2)C6—C71.513 (3)
N1—C11.339 (3)C6—H6A0.9700
N1—C21.462 (3)C6—H6B0.9700
N1—C51.471 (3)C7—C81.490 (3)
O1—C41.413 (3)C8—C91.380 (3)
O1—C31.423 (3)C8—C131.381 (3)
O2—C71.208 (3)C9—C101.371 (4)
C2—C31.493 (3)C9—H90.9300
C2—H2A0.9700C10—C111.368 (4)
C2—H2B0.9700C10—H100.9300
C3—H3A0.9700C11—C121.354 (4)
C3—H3B0.9700C11—H110.9300
C4—C51.503 (4)C12—C131.394 (4)
C4—H4A0.9700C12—H120.9300
C4—H4B0.9700C13—H130.9300
C1—S2—C6101.24 (12)C4—C5—H5B109.7
C1—N1—C2122.6 (2)H5A—C5—H5B108.2
C1—N1—C5125.2 (2)C7—C6—S2114.88 (17)
C2—N1—C5112.0 (2)C7—C6—H6A108.5
C4—O1—C3109.21 (18)S2—C6—H6A108.5
N1—C1—S1124.42 (19)C7—C6—H6B108.5
N1—C1—S2113.49 (18)S2—C6—H6B108.5
S1—C1—S2122.09 (15)H6A—C6—H6B107.5
N1—C2—C3109.6 (2)O2—C7—C8121.4 (2)
N1—C2—H2A109.8O2—C7—C6121.6 (2)
C3—C2—H2A109.8C8—C7—C6116.9 (2)
N1—C2—H2B109.8C9—C8—C13118.6 (3)
C3—C2—H2B109.8C9—C8—C7118.8 (2)
H2A—C2—H2B108.2C13—C8—C7122.6 (3)
O1—C3—C2111.7 (2)C10—C9—C8121.2 (3)
O1—C3—H3A109.3C10—C9—H9119.4
C2—C3—H3A109.3C8—C9—H9119.4
O1—C3—H3B109.3C11—C10—C9119.9 (3)
C2—C3—H3B109.3C11—C10—H10120.1
H3A—C3—H3B107.9C9—C10—H10120.1
O1—C4—C5111.6 (2)C12—C11—C10120.1 (3)
O1—C4—H4A109.3C12—C11—H11120.0
C5—C4—H4A109.3C10—C11—H11120.0
O1—C4—H4B109.3C11—C12—C13120.7 (3)
C5—C4—H4B109.3C11—C12—H12119.7
H4A—C4—H4B108.0C13—C12—H12119.7
N1—C5—C4109.9 (2)C8—C13—C12119.6 (3)
N1—C5—H5A109.7C8—C13—H13120.2
C4—C5—H5A109.7C12—C13—H13120.2
N1—C5—H5B109.7
C2—N1—C1—S11.2 (3)S2—C6—C7—O215.6 (3)
C5—N1—C1—S1176.4 (2)S2—C6—C7—C8166.61 (18)
C2—N1—C1—S2179.28 (17)O2—C7—C8—C98.2 (4)
C5—N1—C1—S24.1 (3)C6—C7—C8—C9174.0 (2)
C6—S2—C1—N1178.53 (17)O2—C7—C8—C13169.9 (2)
C6—S2—C1—S11.95 (18)C6—C7—C8—C137.9 (3)
C1—N1—C2—C3131.3 (2)C13—C8—C9—C100.4 (4)
C5—N1—C2—C352.9 (3)C7—C8—C9—C10178.5 (2)
C4—O1—C3—C261.4 (3)C8—C9—C10—C110.6 (5)
N1—C2—C3—O157.5 (3)C9—C10—C11—C120.8 (5)
C3—O1—C4—C560.5 (3)C10—C11—C12—C130.0 (5)
C1—N1—C5—C4132.1 (2)C9—C8—C13—C121.2 (4)
C2—N1—C5—C452.3 (3)C7—C8—C13—C12179.2 (2)
O1—C4—C5—N156.2 (3)C11—C12—C13—C81.0 (4)
C1—S2—C6—C777.46 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···S10.972.573.065 (3)112
C5—H5A···S20.972.382.928 (6)115
C6—H6B···S10.972.633.024 (3)104
 

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