The title compound, C
11H
6Cl
2N
2O
2S, 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
CCDC reference: 1494850
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C11H6Cl2N2O2S | F(000) = 608 |
Mr = 301.14 | Dx = 1.623 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5731 (9) Å | Cell parameters from 612 reflections |
b = 22.1795 (16) Å | θ = 3.2–28.4° |
c = 8.3093 (16) Å | µ = 0.69 mm−1 |
β = 117.967 (10)° | T = 293 K |
V = 1232.7 (3) Å3 | Block, red |
Z = 4 | 0.18 × 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 Source | 1119 reflections with I > 2σ(I) |
Detector resolution: 16.0454 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 26.0°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −7→9 |
Tmin = 0.712, Tmax = 1.000 | k = −27→12 |
3059 measured reflections | l = −10→5 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-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 reflections | Δρmax = 0.38 e Å−3 |
163 parameters | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.4933 (2) | 0.69183 (7) | 0.38617 (19) | 0.0450 (4) | |
Cl1 | 0.3105 (3) | 0.89412 (7) | 0.2025 (2) | 0.0612 (5) | |
Cl2 | −0.2711 (3) | 0.95859 (7) | −0.4521 (2) | 0.0720 (6) | |
C6 | 0.0675 (8) | 0.8117 (2) | −0.0461 (7) | 0.0369 (14) | |
C7 | 0.1939 (9) | 0.7153 (3) | 0.0411 (7) | 0.0473 (16) | |
H7 | 0.1199 | 0.7042 | −0.0806 | 0.057* | |
C5 | −0.0926 (8) | 0.7988 (3) | −0.2169 (7) | 0.0443 (15) | |
H5 | −0.1307 | 0.7588 | −0.2472 | 0.053* | |
C2 | 0.0113 (9) | 0.9185 (3) | −0.1289 (7) | 0.0468 (16) | |
H2 | 0.0445 | 0.9588 | −0.0990 | 0.056* | |
C4 | −0.1955 (9) | 0.8429 (3) | −0.3414 (7) | 0.0446 (15) | |
H4 | −0.3005 | 0.8328 | −0.4545 | 0.053* | |
O1 | 0.8046 (7) | 0.6438 (2) | 0.7224 (6) | 0.0768 (15) | |
N2 | 0.1847 (7) | 0.7692 (2) | 0.0870 (6) | 0.0429 (12) | |
C10 | 0.4560 (10) | 0.5791 (3) | 0.3021 (8) | 0.0499 (16) | |
H10 | 0.4750 | 0.5376 | 0.3102 | 0.060* | |
N1 | 0.7237 (8) | 0.6023 (2) | 0.6127 (7) | 0.0538 (14) | |
C1 | 0.1141 (8) | 0.8726 (2) | −0.0056 (7) | 0.0395 (14) | |
O2 | 0.7734 (7) | 0.5493 (2) | 0.6444 (6) | 0.0761 (15) | |
C9 | 0.3146 (9) | 0.6094 (3) | 0.1475 (7) | 0.0495 (17) | |
H9 | 0.2288 | 0.5902 | 0.0393 | 0.059* | |
C11 | 0.5608 (9) | 0.6182 (3) | 0.4372 (8) | 0.0450 (15) | |
C8 | 0.3165 (9) | 0.6706 (3) | 0.1730 (7) | 0.0445 (15) | |
C3 | −0.1422 (9) | 0.9020 (3) | −0.2976 (7) | 0.0436 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0440 (10) | 0.0394 (9) | 0.0480 (9) | 0.0004 (8) | 0.0184 (8) | 0.0007 (7) |
Cl1 | 0.0617 (12) | 0.0609 (11) | 0.0451 (9) | −0.0060 (9) | 0.0118 (9) | −0.0096 (8) |
Cl2 | 0.0749 (15) | 0.0527 (10) | 0.0616 (11) | 0.0061 (10) | 0.0096 (11) | 0.0135 (9) |
C6 | 0.041 (4) | 0.038 (3) | 0.036 (3) | 0.004 (3) | 0.022 (3) | 0.004 (3) |
C7 | 0.051 (4) | 0.050 (4) | 0.037 (3) | 0.000 (3) | 0.017 (3) | 0.002 (3) |
C5 | 0.037 (4) | 0.039 (3) | 0.046 (3) | 0.003 (3) | 0.009 (3) | 0.002 (3) |
C2 | 0.051 (4) | 0.042 (4) | 0.053 (4) | −0.009 (3) | 0.029 (4) | −0.003 (3) |
C4 | 0.041 (4) | 0.047 (4) | 0.033 (3) | 0.001 (3) | 0.007 (3) | 0.001 (3) |
O1 | 0.069 (4) | 0.067 (3) | 0.060 (3) | −0.008 (3) | 0.001 (3) | −0.003 (3) |
N2 | 0.042 (3) | 0.037 (3) | 0.045 (3) | −0.005 (2) | 0.016 (3) | −0.001 (2) |
C10 | 0.064 (5) | 0.036 (3) | 0.060 (4) | 0.006 (3) | 0.038 (4) | 0.003 (3) |
N1 | 0.049 (4) | 0.055 (4) | 0.061 (4) | 0.004 (3) | 0.029 (3) | 0.007 (3) |
C1 | 0.037 (4) | 0.044 (4) | 0.036 (3) | −0.006 (3) | 0.016 (3) | −0.004 (3) |
O2 | 0.086 (4) | 0.053 (3) | 0.082 (3) | 0.028 (3) | 0.033 (3) | 0.021 (2) |
C9 | 0.052 (5) | 0.053 (4) | 0.036 (3) | −0.001 (3) | 0.014 (3) | −0.001 (3) |
C11 | 0.049 (4) | 0.039 (3) | 0.049 (4) | −0.004 (3) | 0.025 (4) | 0.002 (3) |
C8 | 0.042 (4) | 0.042 (3) | 0.046 (4) | 0.003 (3) | 0.018 (3) | 0.003 (3) |
C3 | 0.041 (4) | 0.049 (4) | 0.033 (3) | 0.003 (3) | 0.011 (3) | 0.005 (3) |
Geometric parameters (Å, º) top
S1—C11 | 1.703 (6) | C2—C1 | 1.394 (7) |
S1—C8 | 1.711 (6) | C2—H2 | 0.9300 |
Cl1—C1 | 1.737 (5) | C4—C3 | 1.370 (7) |
Cl2—C3 | 1.732 (6) | C4—H4 | 0.9300 |
C6—C5 | 1.397 (7) | O1—N1 | 1.237 (6) |
C6—C1 | 1.398 (7) | C10—C11 | 1.344 (7) |
C6—N2 | 1.407 (6) | C10—C9 | 1.399 (7) |
C7—N2 | 1.267 (6) | C10—H10 | 0.9300 |
C7—C8 | 1.446 (7) | N1—O2 | 1.226 (6) |
C7—H7 | 0.9300 | N1—C11 | 1.445 (7) |
C5—C4 | 1.371 (7) | C9—C8 | 1.372 (7) |
C5—H5 | 0.9300 | C9—H9 | 0.9300 |
C2—C3 | 1.386 (7) | | |
| | | |
C11—S1—C8 | 89.5 (3) | C9—C10—H10 | 124.6 |
C5—C6—C1 | 116.3 (5) | O2—N1—O1 | 124.1 (6) |
C5—C6—N2 | 126.1 (5) | O2—N1—C11 | 118.8 (5) |
C1—C6—N2 | 117.6 (5) | O1—N1—C11 | 117.1 (5) |
N2—C7—C8 | 121.7 (5) | C2—C1—C6 | 122.5 (5) |
N2—C7—H7 | 119.2 | C2—C1—Cl1 | 117.0 (4) |
C8—C7—H7 | 119.2 | C6—C1—Cl1 | 120.4 (4) |
C4—C5—C6 | 122.5 (6) | C8—C9—C10 | 112.6 (5) |
C4—C5—H5 | 118.8 | C8—C9—H9 | 123.7 |
C6—C5—H5 | 118.8 | C10—C9—H9 | 123.7 |
C3—C2—C1 | 117.8 (5) | C10—C11—N1 | 125.2 (6) |
C3—C2—H2 | 121.1 | C10—C11—S1 | 114.8 (5) |
C1—C2—H2 | 121.1 | N1—C11—S1 | 120.0 (4) |
C3—C4—C5 | 119.3 (5) | C9—C8—C7 | 127.2 (6) |
C3—C4—H4 | 120.3 | C9—C8—S1 | 112.2 (4) |
C5—C4—H4 | 120.3 | C7—C8—S1 | 120.6 (5) |
C7—N2—C6 | 119.9 (5) | C4—C3—C2 | 121.6 (5) |
C11—C10—C9 | 110.8 (6) | C4—C3—Cl2 | 120.2 (4) |
C11—C10—H10 | 124.6 | C2—C3—Cl2 | 118.2 (5) |
| | | |
C1—C6—C5—C4 | 2.0 (8) | O1—N1—C11—C10 | −179.9 (6) |
N2—C6—C5—C4 | −177.9 (5) | O2—N1—C11—S1 | −177.9 (5) |
C6—C5—C4—C3 | −0.7 (9) | O1—N1—C11—S1 | 2.2 (7) |
C8—C7—N2—C6 | 178.5 (5) | C8—S1—C11—C10 | −0.3 (5) |
C5—C6—N2—C7 | 22.1 (9) | C8—S1—C11—N1 | 177.9 (5) |
C1—C6—N2—C7 | −157.7 (5) | C10—C9—C8—C7 | 178.5 (5) |
C3—C2—C1—C6 | −0.2 (8) | C10—C9—C8—S1 | 0.6 (7) |
C3—C2—C1—Cl1 | 178.2 (4) | N2—C7—C8—C9 | 168.4 (6) |
C5—C6—C1—C2 | −1.5 (8) | N2—C7—C8—S1 | −13.8 (8) |
N2—C6—C1—C2 | 178.4 (5) | C11—S1—C8—C9 | −0.2 (5) |
C5—C6—C1—Cl1 | −179.9 (3) | C11—S1—C8—C7 | −178.3 (5) |
N2—C6—C1—Cl1 | 0.0 (7) | C5—C4—C3—C2 | −1.2 (9) |
C11—C10—C9—C8 | −0.8 (8) | C5—C4—C3—Cl2 | −179.6 (4) |
C9—C10—C11—N1 | −177.4 (5) | C1—C2—C3—C4 | 1.6 (8) |
C9—C10—C11—S1 | 0.6 (7) | C1—C2—C3—Cl2 | −180.0 (4) |
O2—N1—C11—C10 | 0.0 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.59 | 3.508 (8) | 171 |
C7—H7···O1i | 0.93 | 2.55 | 3.300 (8) | 138 |
C2—H2···O2ii | 0.93 | 2.56 | 3.360 (7) | 144 |
Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, y+1/2, −z+1/2. |