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In the title compound, C11H15Cl3N2O2S2, the thio­morpholine ring adopts a chair conformation and the butadiene has a conformation closer to cisoid than to transoid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045211/dn2078sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045211/dn2078Isup2.hkl
Contains datablock I

CCDC reference: 629643

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.075
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O2 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3,4,4-Trichloro-2-nitro-1-propylsulfanyl-1-(4-thiomorpholinyl)buta-1,3-diene top
Crystal data top
C11H15Cl3N2O2S2F(000) = 776.00
Mr = 377.73Dx = 1.530 Mg m3
Monoclinic, P21/nMelting point: 425 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 11.3127 (5) ÅCell parameters from 9300 reflections
b = 9.1100 (3) Åθ = 2.8–25.3°
c = 16.3114 (8) ŵ = 0.81 mm1
β = 102.803 (2)°T = 294 K
V = 1639.24 (12) Å3Platelet, yellow
Z = 40.40 × 0.20 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID S
diffractometer
2824 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.039
ω scansθmax = 25.2°, θmin = 2.9°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.820, Tmax = 0.852k = 010
63776 measured reflectionsl = 019
2824 independent reflections
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)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.48 w = 1/[σ2(Fo2) + (0.0165P)2 + 2.4574P]
where P = (Fo2 + 2Fc2)/3
2824 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.25 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
Cl30.13819 (11)0.02140 (17)0.04376 (9)0.0742 (4)
Cl10.52310 (12)0.02457 (18)0.11238 (10)0.0826 (5)
Cl20.32805 (17)0.23042 (16)0.06265 (11)0.0917 (5)
S10.34076 (11)0.17623 (16)0.25363 (8)0.0609 (4)
S20.69722 (14)0.57653 (18)0.23389 (11)0.0826 (5)
O20.2925 (3)0.4442 (4)0.0343 (2)0.0685 (10)
O10.2546 (3)0.2564 (4)0.0487 (2)0.0716 (10)
N20.4659 (3)0.3734 (4)0.1834 (2)0.0479 (9)
N10.2916 (3)0.3094 (4)0.0222 (2)0.0549 (10)
C30.3273 (4)0.2124 (5)0.0907 (3)0.0452 (10)
C110.5327 (4)0.4140 (6)0.1189 (3)0.0561 (12)
H11A0.49980.50460.09190.067*
H11B0.52240.33800.07630.067*
C40.3840 (4)0.2649 (5)0.1701 (3)0.0459 (10)
C80.4765 (5)0.4775 (6)0.2535 (3)0.0618 (13)
H8A0.42990.44100.29240.074*
H8B0.44200.57090.23180.074*
C20.2928 (4)0.0599 (5)0.0731 (3)0.0497 (11)
C90.6068 (5)0.5014 (6)0.3005 (3)0.0742 (16)
H9A0.64120.40840.32310.089*
H9B0.60800.56750.34730.089*
C10.3701 (5)0.0499 (5)0.0803 (3)0.0577 (12)
C100.6661 (4)0.4340 (6)0.1570 (3)0.0632 (13)
H10A0.70780.45600.11250.076*
H10B0.69860.34240.18290.076*
C50.4808 (5)0.1548 (7)0.3338 (3)0.0745 (16)
H5A0.54920.14920.30700.089*
H5B0.49230.23960.37070.089*
C60.4764 (7)0.0199 (9)0.3840 (4)0.103 (2)
H6A0.54650.01960.43070.124*
H6B0.40480.02480.40750.124*
C70.4738 (8)0.1176 (8)0.3396 (6)0.127 (3)
H7A0.39870.12590.29870.191*
H7B0.48090.19740.37870.191*
H7C0.54020.12070.31170.191*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl30.0490 (7)0.0909 (10)0.0767 (9)0.0181 (7)0.0010 (6)0.0063 (8)
Cl10.0565 (8)0.0912 (11)0.0983 (11)0.0222 (7)0.0131 (7)0.0130 (9)
Cl20.1273 (14)0.0484 (8)0.1033 (12)0.0018 (8)0.0338 (10)0.0062 (8)
S10.0537 (7)0.0801 (9)0.0477 (6)0.0081 (6)0.0086 (5)0.0066 (6)
S20.0738 (9)0.0733 (10)0.0913 (11)0.0252 (8)0.0021 (8)0.0032 (8)
O20.078 (2)0.048 (2)0.069 (2)0.0069 (17)0.0069 (18)0.0042 (17)
O10.086 (3)0.073 (2)0.0442 (19)0.002 (2)0.0092 (17)0.0018 (18)
N20.049 (2)0.051 (2)0.0417 (19)0.0047 (17)0.0055 (16)0.0045 (17)
N10.056 (2)0.052 (2)0.051 (2)0.0007 (19)0.0002 (18)0.0002 (19)
C30.041 (2)0.047 (2)0.043 (2)0.0032 (19)0.0012 (18)0.003 (2)
C110.058 (3)0.056 (3)0.052 (3)0.005 (2)0.008 (2)0.002 (2)
C40.040 (2)0.050 (3)0.047 (2)0.005 (2)0.0079 (18)0.001 (2)
C80.067 (3)0.061 (3)0.054 (3)0.001 (3)0.006 (2)0.008 (2)
C20.042 (2)0.055 (3)0.048 (2)0.002 (2)0.0030 (19)0.002 (2)
C90.089 (4)0.068 (4)0.056 (3)0.011 (3)0.005 (3)0.007 (3)
C10.066 (3)0.051 (3)0.055 (3)0.002 (2)0.011 (2)0.000 (2)
C100.052 (3)0.060 (3)0.076 (3)0.006 (2)0.011 (2)0.003 (3)
C50.073 (4)0.090 (4)0.052 (3)0.010 (3)0.006 (3)0.014 (3)
C60.095 (5)0.118 (6)0.089 (5)0.010 (4)0.007 (4)0.041 (5)
C70.131 (7)0.078 (5)0.164 (8)0.018 (5)0.013 (6)0.026 (6)
Geometric parameters (Å, º) top
Cl3—C21.744 (4)C8—C91.518 (7)
Cl1—C11.710 (5)C8—H8A0.9700
Cl2—C11.719 (5)C8—H8B0.9700
S1—C41.744 (4)C2—C11.316 (6)
S1—C51.828 (5)C9—H9A0.9700
S2—C101.785 (5)C9—H9B0.9700
S2—C91.786 (6)C10—H10A0.9700
O2—N11.243 (5)C10—H10B0.9700
O1—N11.238 (5)C5—C61.484 (8)
N2—C41.340 (5)C5—H5A0.9700
N2—C81.470 (6)C5—H5B0.9700
N2—C111.472 (6)C6—C71.444 (10)
N1—C31.411 (5)C6—H6A0.9700
C3—C41.397 (6)C6—H6B0.9700
C3—C21.454 (6)C7—H7A0.9600
C11—C101.511 (6)C7—H7B0.9600
C11—H11A0.9700C7—H7C0.9600
C11—H11B0.9700
C4—S1—C5105.1 (2)S2—C9—H9A109.3
C10—S2—C995.6 (3)C8—C9—H9B109.3
C4—N2—C8122.4 (4)S2—C9—H9B109.3
C4—N2—C11121.1 (4)H9A—C9—H9B107.9
C8—N2—C11115.3 (4)C2—C1—Cl1122.2 (4)
O1—N1—O2121.5 (4)C2—C1—Cl2124.0 (4)
O1—N1—C3118.3 (4)Cl1—C1—Cl2113.8 (3)
O2—N1—C3120.1 (4)C11—C10—S2113.6 (4)
C4—C3—N1120.8 (4)C11—C10—H10A108.8
C4—C3—C2123.9 (4)S2—C10—H10A108.8
N1—C3—C2115.2 (4)C11—C10—H10B108.8
N2—C11—C10111.1 (4)S2—C10—H10B108.8
N2—C11—H11A109.4H10A—C10—H10B107.7
C10—C11—H11A109.4C6—C5—S1110.7 (4)
N2—C11—H11B109.4C6—C5—H5A109.5
C10—C11—H11B109.4S1—C5—H5A109.5
H11A—C11—H11B108.0C6—C5—H5B109.5
N2—C4—C3124.1 (4)S1—C5—H5B109.5
N2—C4—S1121.3 (3)H5A—C5—H5B108.1
C3—C4—S1114.6 (3)C7—C6—C5116.1 (6)
N2—C8—C9112.9 (4)C7—C6—H6A108.3
N2—C8—H8A109.0C5—C6—H6A108.3
C9—C8—H8A109.0C7—C6—H6B108.3
N2—C8—H8B109.0C5—C6—H6B108.3
C9—C8—H8B109.0H6A—C6—H6B107.4
H8A—C8—H8B107.8C6—C7—H7A109.5
C1—C2—C3124.4 (4)C6—C7—H7B109.5
C1—C2—Cl3118.5 (4)H7A—C7—H7B109.5
C3—C2—Cl3117.1 (3)C6—C7—H7C109.5
C8—C9—S2111.7 (4)H7A—C7—H7C109.5
C8—C9—H9A109.3H7B—C7—H7C109.5
 

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