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The title compound, C11H6Cl2N2O2S, is a Schiff base that incorporates an N-bound 2,4-di­chloro­phenyl and a C-bound 5-nitro­thio­phene ring. The crystal structure features C—H...O hydrogen bonds and π–π stacking inter­actions. Geometric parameters from quantum-chemical calculations are in good agreement with experimental X-ray diffraction results.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011816/pk2586sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011816/pk2586Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016011816/pk2586Isup3.cml
Supplementary material

CCDC reference: 1494850

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.063
  • wR factor = 0.138
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full value Low . 0.919 Note
Author Response: There is no adequate reflection data.

Alert level B PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 175 Report
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0084 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 5.122 Check PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT128_ALERT_4_G Alternate Setting for Input Space Group P21/c P21/n Note PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 4 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 41 Note
1 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 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 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

2,4-Dichloro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline top
Crystal data top
C11H6Cl2N2O2SF(000) = 608
Mr = 301.14Dx = 1.623 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.5731 (9) ÅCell parameters from 612 reflections
b = 22.1795 (16) Åθ = 3.2–28.4°
c = 8.3093 (16) ŵ = 0.69 mm1
β = 117.967 (10)°T = 293 K
V = 1232.7 (3) Å3Block, red
Z = 40.18 × 0.15 × 0.10 mm
Data collection top
Agilent SuperNova (Single source at offset) Eos
diffractometer
2201 independent reflections
Radiation source: SuperNova (Mo) X-ray Source1119 reflections with I > 2σ(I)
Detector resolution: 16.0454 pixels mm-1Rint = 0.033
ω scansθmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
h = 79
Tmin = 0.712, Tmax = 1.000k = 2712
3059 measured reflectionsl = 105
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.019P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2201 reflectionsΔρmax = 0.38 e Å3
163 parametersΔρmin = 0.32 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.4933 (2)0.69183 (7)0.38617 (19)0.0450 (4)
Cl10.3105 (3)0.89412 (7)0.2025 (2)0.0612 (5)
Cl20.2711 (3)0.95859 (7)0.4521 (2)0.0720 (6)
C60.0675 (8)0.8117 (2)0.0461 (7)0.0369 (14)
C70.1939 (9)0.7153 (3)0.0411 (7)0.0473 (16)
H70.11990.70420.08060.057*
C50.0926 (8)0.7988 (3)0.2169 (7)0.0443 (15)
H50.13070.75880.24720.053*
C20.0113 (9)0.9185 (3)0.1289 (7)0.0468 (16)
H20.04450.95880.09900.056*
C40.1955 (9)0.8429 (3)0.3414 (7)0.0446 (15)
H40.30050.83280.45450.053*
O10.8046 (7)0.6438 (2)0.7224 (6)0.0768 (15)
N20.1847 (7)0.7692 (2)0.0870 (6)0.0429 (12)
C100.4560 (10)0.5791 (3)0.3021 (8)0.0499 (16)
H100.47500.53760.31020.060*
N10.7237 (8)0.6023 (2)0.6127 (7)0.0538 (14)
C10.1141 (8)0.8726 (2)0.0056 (7)0.0395 (14)
O20.7734 (7)0.5493 (2)0.6444 (6)0.0761 (15)
C90.3146 (9)0.6094 (3)0.1475 (7)0.0495 (17)
H90.22880.59020.03930.059*
C110.5608 (9)0.6182 (3)0.4372 (8)0.0450 (15)
C80.3165 (9)0.6706 (3)0.1730 (7)0.0445 (15)
C30.1422 (9)0.9020 (3)0.2976 (7)0.0436 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0440 (10)0.0394 (9)0.0480 (9)0.0004 (8)0.0184 (8)0.0007 (7)
Cl10.0617 (12)0.0609 (11)0.0451 (9)0.0060 (9)0.0118 (9)0.0096 (8)
Cl20.0749 (15)0.0527 (10)0.0616 (11)0.0061 (10)0.0096 (11)0.0135 (9)
C60.041 (4)0.038 (3)0.036 (3)0.004 (3)0.022 (3)0.004 (3)
C70.051 (4)0.050 (4)0.037 (3)0.000 (3)0.017 (3)0.002 (3)
C50.037 (4)0.039 (3)0.046 (3)0.003 (3)0.009 (3)0.002 (3)
C20.051 (4)0.042 (4)0.053 (4)0.009 (3)0.029 (4)0.003 (3)
C40.041 (4)0.047 (4)0.033 (3)0.001 (3)0.007 (3)0.001 (3)
O10.069 (4)0.067 (3)0.060 (3)0.008 (3)0.001 (3)0.003 (3)
N20.042 (3)0.037 (3)0.045 (3)0.005 (2)0.016 (3)0.001 (2)
C100.064 (5)0.036 (3)0.060 (4)0.006 (3)0.038 (4)0.003 (3)
N10.049 (4)0.055 (4)0.061 (4)0.004 (3)0.029 (3)0.007 (3)
C10.037 (4)0.044 (4)0.036 (3)0.006 (3)0.016 (3)0.004 (3)
O20.086 (4)0.053 (3)0.082 (3)0.028 (3)0.033 (3)0.021 (2)
C90.052 (5)0.053 (4)0.036 (3)0.001 (3)0.014 (3)0.001 (3)
C110.049 (4)0.039 (3)0.049 (4)0.004 (3)0.025 (4)0.002 (3)
C80.042 (4)0.042 (3)0.046 (4)0.003 (3)0.018 (3)0.003 (3)
C30.041 (4)0.049 (4)0.033 (3)0.003 (3)0.011 (3)0.005 (3)
Geometric parameters (Å, º) top
S1—C111.703 (6)C2—C11.394 (7)
S1—C81.711 (6)C2—H20.9300
Cl1—C11.737 (5)C4—C31.370 (7)
Cl2—C31.732 (6)C4—H40.9300
C6—C51.397 (7)O1—N11.237 (6)
C6—C11.398 (7)C10—C111.344 (7)
C6—N21.407 (6)C10—C91.399 (7)
C7—N21.267 (6)C10—H100.9300
C7—C81.446 (7)N1—O21.226 (6)
C7—H70.9300N1—C111.445 (7)
C5—C41.371 (7)C9—C81.372 (7)
C5—H50.9300C9—H90.9300
C2—C31.386 (7)
C11—S1—C889.5 (3)C9—C10—H10124.6
C5—C6—C1116.3 (5)O2—N1—O1124.1 (6)
C5—C6—N2126.1 (5)O2—N1—C11118.8 (5)
C1—C6—N2117.6 (5)O1—N1—C11117.1 (5)
N2—C7—C8121.7 (5)C2—C1—C6122.5 (5)
N2—C7—H7119.2C2—C1—Cl1117.0 (4)
C8—C7—H7119.2C6—C1—Cl1120.4 (4)
C4—C5—C6122.5 (6)C8—C9—C10112.6 (5)
C4—C5—H5118.8C8—C9—H9123.7
C6—C5—H5118.8C10—C9—H9123.7
C3—C2—C1117.8 (5)C10—C11—N1125.2 (6)
C3—C2—H2121.1C10—C11—S1114.8 (5)
C1—C2—H2121.1N1—C11—S1120.0 (4)
C3—C4—C5119.3 (5)C9—C8—C7127.2 (6)
C3—C4—H4120.3C9—C8—S1112.2 (4)
C5—C4—H4120.3C7—C8—S1120.6 (5)
C7—N2—C6119.9 (5)C4—C3—C2121.6 (5)
C11—C10—C9110.8 (6)C4—C3—Cl2120.2 (4)
C11—C10—H10124.6C2—C3—Cl2118.2 (5)
C1—C6—C5—C42.0 (8)O1—N1—C11—C10179.9 (6)
N2—C6—C5—C4177.9 (5)O2—N1—C11—S1177.9 (5)
C6—C5—C4—C30.7 (9)O1—N1—C11—S12.2 (7)
C8—C7—N2—C6178.5 (5)C8—S1—C11—C100.3 (5)
C5—C6—N2—C722.1 (9)C8—S1—C11—N1177.9 (5)
C1—C6—N2—C7157.7 (5)C10—C9—C8—C7178.5 (5)
C3—C2—C1—C60.2 (8)C10—C9—C8—S10.6 (7)
C3—C2—C1—Cl1178.2 (4)N2—C7—C8—C9168.4 (6)
C5—C6—C1—C21.5 (8)N2—C7—C8—S113.8 (8)
N2—C6—C1—C2178.4 (5)C11—S1—C8—C90.2 (5)
C5—C6—C1—Cl1179.9 (3)C11—S1—C8—C7178.3 (5)
N2—C6—C1—Cl10.0 (7)C5—C4—C3—C21.2 (9)
C11—C10—C9—C80.8 (8)C5—C4—C3—Cl2179.6 (4)
C9—C10—C11—N1177.4 (5)C1—C2—C3—C41.6 (8)
C9—C10—C11—S10.6 (7)C1—C2—C3—Cl2180.0 (4)
O2—N1—C11—C100.0 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.593.508 (8)171
C7—H7···O1i0.932.553.300 (8)138
C2—H2···O2ii0.932.563.360 (7)144
Symmetry codes: (i) x1, y, z1; (ii) x+1, y+1/2, z+1/2.
 

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