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The structure of the title compound, C15H13N3S, comprises planar mol­ecules. The dihedral angle between the quinoline and thio­phene rings is 2.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800019607/ob6015sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800019607/ob6015Isup2.hkl
Contains datablock I

CCDC reference: 155886

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.061
  • wR factor = 0.170
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.121 PLAT_420 Alert C D-H without acceptor N(11) - H(11) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Two distinct crystal colours (orange and yellow) were observed in the bulk following crystallization of the title compound, (I). The molecular structures from both crystal types were determined and proved to be identical, as were the melting points. Both structures refined to approximately the same R value and the structure obtained from the orange crystals is reported here. The cell for the yellow crystals was determined as a = 10.1194 (9), b = 14.251 (1), c = 18.136 (2) Å and V = 2615.4 (4) Å3. The origin of the difference in colour is currently unknown and cannot be simply explained by crystal morphology because both crystal types were indistinguishable in size and shape. However, we cannot disguard the possibility of two different rates of crystallization; which we are currently investigating.

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals were grown from an aqueous solution.

Refinement top

All H atoms were included in the refinement at calculated positions as riding models with C—H set to 0.95 (Ar—H) and 0.98 Å (CH3), except for the amine H atom, which was located on difference syntheses and for which both positional and displacement parameters were refined. The higher than expected Rint value (>0.10) may be due to a slight missalignment of the crystal plate on the diffractometer with respect to the beam.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom numbering scheme for (I), showing 30% probability ellipsoids.
(E)-1-(2-Thienyl)ethanone 8-quinolylhydrozone top
Crystal data top
C15H13N3SDx = 1.357 Mg m3
Mr = 267.34Melting point: 432-434 K K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 10.148 (2) ÅCell parameters from 46446 reflections
b = 14.251 (3) Åθ = 1.0–27.5°
c = 18.103 (4) ŵ = 0.24 mm1
V = 2618.1 (9) Å3T = 150 K
Z = 8Plate, orange
F(000) = 11200.30 × 0.24 × 0.02 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
2947 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode1498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.121
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.3°
ϕ and ω scansh = 1113
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1818
Tmin = 0.933, Tmax = 0.995l = 2321
20334 measured 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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0867P)2]
where P = (Fo2 + 2Fc2)/3
2947 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C15H13N3SV = 2618.1 (9) Å3
Mr = 267.34Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.148 (2) ŵ = 0.24 mm1
b = 14.251 (3) ÅT = 150 K
c = 18.103 (4) Å0.30 × 0.24 × 0.02 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
2947 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
1498 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.995Rint = 0.121
20334 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.32 e Å3
2947 reflectionsΔρmin = 0.33 e Å3
177 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.2482 (0.0081) x - 6.6174 (0.0154) y + 9.4806 (0.0175) z = 3.4205 (0.0145)

* -0.0012 (0.0019) N1 * 0.0030 (0.0021) C2 * -0.0025 (0.0021) C3 * 0.0006 (0.0021) C4 * 0.0011 (0.0019) C10 * -0.0009 (0.0020) C9 0.0028 (0.0047) C5 0.0120 (0.0054) C6 0.0109 (0.0051) C7 0.0108 (0.0041) C8

Rms deviation of fitted atoms = 0.0018

7.3426 (0.0092) x - 6.9706 (0.0171) y + 8.8178 (0.0181) z = 2.7969 (0.0120)

Angle to previous plane (with approximate e.s.d.) = 2.59 (0.19)

* -0.0022 (0.0014) S15 * 0.0044 (0.0016) C16 * -0.0051 (0.0019) C17 * 0.0031 (0.0020) C18 * -0.0002 (0.0018) C19

Rms deviation of fitted atoms = 0.0035

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5693 (2)0.64109 (18)0.37293 (13)0.0418 (7)
C20.6529 (3)0.7026 (2)0.35234 (16)0.0381 (8)
H20.66260.75620.38310.048*
C30.7324 (3)0.6993 (2)0.28868 (19)0.0494 (9)
H30.79200.74850.27680.062*
C40.7195 (3)0.6214 (2)0.24448 (17)0.0471 (9)
H40.77120.61540.20100.059*
C50.6099 (3)0.4681 (2)0.22149 (17)0.0433 (8)
H50.65820.45830.17720.054*
C60.5212 (3)0.4034 (2)0.24518 (18)0.0462 (8)
H60.50880.34800.21680.058*
C70.4480 (3)0.4150 (2)0.30912 (16)0.0403 (8)
H70.38640.36830.32350.050*
C80.4644 (3)0.4946 (2)0.35212 (15)0.0357 (7)
C90.5564 (3)0.5637 (2)0.32874 (16)0.0369 (7)
C100.6294 (3)0.5505 (2)0.26396 (16)0.0387 (8)
N110.3944 (3)0.5114 (2)0.41531 (14)0.0417 (7)
H110.414 (3)0.564 (3)0.4480 (18)0.065 (11)*
N120.3027 (2)0.44926 (17)0.43975 (14)0.0371 (6)
C130.2338 (3)0.4690 (2)0.49707 (16)0.0354 (7)
C140.2482 (3)0.5580 (2)0.54076 (16)0.0417 (8)
H1410.34070.56640.55480.052*
H1420.19360.55420.58530.052*
H1430.21960.61130.51060.052*
S150.10862 (8)0.30193 (6)0.46517 (4)0.0436 (3)
C160.1370 (3)0.4000 (2)0.51981 (15)0.0333 (7)
C170.0599 (3)0.3978 (2)0.58123 (17)0.0448 (8)
H170.05970.44550.61790.056*
C180.0204 (3)0.3163 (2)0.58454 (18)0.0475 (9)
H180.07930.30320.62400.059*
C190.0041 (3)0.2597 (2)0.52583 (16)0.0432 (8)
H190.05050.20240.51910.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0371 (16)0.0437 (17)0.0447 (15)0.0006 (13)0.0044 (12)0.0032 (13)
C20.0367 (18)0.0368 (19)0.0409 (18)0.0009 (15)0.0032 (15)0.0027 (13)
C30.0344 (19)0.051 (2)0.063 (2)0.0020 (16)0.0026 (17)0.0130 (17)
C40.0285 (18)0.067 (3)0.0457 (19)0.0109 (17)0.0083 (15)0.0128 (17)
C50.0369 (19)0.055 (2)0.0381 (18)0.0110 (16)0.0035 (15)0.0017 (15)
C60.0389 (19)0.048 (2)0.051 (2)0.0077 (17)0.0023 (16)0.0037 (16)
C70.0333 (18)0.046 (2)0.0420 (18)0.0024 (15)0.0013 (15)0.0016 (15)
C80.0278 (17)0.0418 (19)0.0374 (17)0.0035 (14)0.0045 (14)0.0054 (14)
C90.0267 (17)0.045 (2)0.0387 (17)0.0071 (15)0.0033 (14)0.0033 (14)
C100.0291 (18)0.047 (2)0.0397 (19)0.0063 (14)0.0009 (14)0.0114 (14)
N110.0401 (16)0.0489 (17)0.0361 (15)0.0052 (13)0.0044 (13)0.0028 (13)
N120.0324 (14)0.0371 (15)0.0418 (15)0.0018 (12)0.0000 (12)0.0068 (11)
C130.0315 (17)0.0408 (19)0.0337 (17)0.0046 (14)0.0046 (14)0.0041 (13)
C140.0421 (19)0.0374 (18)0.0456 (19)0.0008 (14)0.0036 (15)0.0022 (14)
S150.0419 (5)0.0418 (5)0.0470 (5)0.0019 (4)0.0060 (4)0.0015 (3)
C160.0277 (17)0.0350 (17)0.0371 (17)0.0041 (13)0.0045 (13)0.0036 (12)
C170.043 (2)0.048 (2)0.0434 (19)0.0026 (16)0.0062 (15)0.0001 (15)
C180.040 (2)0.054 (2)0.048 (2)0.0023 (17)0.0051 (15)0.0054 (16)
C190.0346 (18)0.0404 (19)0.055 (2)0.0003 (15)0.0046 (15)0.0030 (15)
Geometric parameters (Å, º) top
N1—C21.276 (4)C9—C101.400 (4)
N1—C91.369 (4)N11—N121.359 (3)
C2—C31.407 (4)N11—H110.97 (4)
C2—H20.9500N12—C131.283 (4)
C3—C41.375 (5)C13—C161.449 (4)
C3—H30.9500C13—C141.501 (4)
C4—C101.406 (4)C14—H1410.9800
C4—H40.9500C14—H1420.9800
C5—C61.359 (4)C14—H1430.9800
C5—C101.418 (4)S15—C191.696 (3)
C5—H50.9500S15—C161.736 (3)
C6—C71.385 (4)C16—C171.360 (4)
C6—H60.9500C17—C181.420 (4)
C7—C81.386 (4)C17—H170.9500
C7—H70.9500C18—C191.345 (4)
C8—N111.368 (4)C18—H180.9500
C8—C91.421 (4)C19—H190.9500
C2—N1—C9116.5 (3)C4—C10—C5123.3 (3)
N1—C2—C3126.7 (3)N12—N11—C8121.0 (3)
N1—C2—H2116.7N12—N11—H11116 (2)
C3—C2—H2116.7C8—N11—H11123 (2)
C4—C3—C2116.7 (3)C13—N12—N11119.6 (3)
C4—C3—H3121.7N12—C13—C16116.7 (3)
C2—C3—H3121.7N12—C13—C14124.0 (3)
C3—C4—C10119.7 (3)C16—C13—C14119.3 (3)
C3—C4—H4120.1C13—C14—H141109.5
C10—C4—H4120.1C13—C14—H142109.5
C6—C5—C10118.9 (3)H141—C14—H142109.5
C6—C5—H5120.5C13—C14—H143109.5
C10—C5—H5120.5H141—C14—H143109.5
C5—C6—C7122.5 (3)H142—C14—H143109.5
C5—C6—H6118.7C19—S15—C1691.66 (15)
C7—C6—H6118.7C17—C16—C13129.6 (3)
C6—C7—C8120.2 (3)C17—C16—S15110.6 (2)
C6—C7—H7119.9C13—C16—S15119.8 (2)
C8—C7—H7119.9C16—C17—C18112.6 (3)
N11—C8—C7123.4 (3)C16—C17—H17123.7
N11—C8—C9118.0 (3)C18—C17—H17123.7
C7—C8—C9118.6 (3)C19—C18—C17112.8 (3)
N1—C9—C10123.2 (3)C19—C18—H18123.6
N1—C9—C8116.5 (3)C17—C18—H18123.6
C10—C9—C8120.3 (3)C18—C19—S15112.4 (3)
C9—C10—C4117.3 (3)C18—C19—H19123.8
C9—C10—C5119.4 (3)S15—C19—H19123.8
C9—N1—C2—C30.5 (5)C6—C5—C10—C90.5 (4)
N1—C2—C3—C40.7 (5)C6—C5—C10—C4179.6 (3)
C2—C3—C4—C100.4 (4)C7—C8—N11—N120.0 (4)
C10—C5—C6—C70.4 (5)C9—C8—N11—N12178.5 (2)
C5—C6—C7—C80.5 (5)C8—N11—N12—C13176.5 (3)
C6—C7—C8—N11179.1 (3)N11—N12—C13—C16179.5 (2)
C6—C7—C8—C90.6 (4)N11—N12—C13—C140.5 (4)
C2—N1—C9—C100.1 (4)N12—C13—C16—C17173.2 (3)
C2—N1—C9—C8179.3 (3)C14—C13—C16—C176.7 (4)
N11—C8—C9—N11.4 (4)N12—C13—C16—S155.9 (3)
C7—C8—C9—N1180.0 (3)C14—C13—C16—S15174.1 (2)
N11—C8—C9—C10179.2 (3)C19—S15—C16—C170.6 (2)
C7—C8—C9—C100.6 (4)C19—S15—C16—C13178.7 (2)
N1—C9—C10—C40.1 (4)C13—C16—C17—C18178.3 (3)
C8—C9—C10—C4179.5 (2)S15—C16—C17—C180.9 (3)
N1—C9—C10—C5179.9 (3)C16—C17—C18—C190.9 (4)
C8—C9—C10—C50.6 (4)C17—C18—C19—S150.4 (4)
C3—C4—C10—C90.0 (4)C16—S15—C19—C180.1 (3)
C3—C4—C10—C5179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···N10.97 (4)2.36 (3)2.675 (4)98 (2)

Experimental details

Crystal data
Chemical formulaC15H13N3S
Mr267.34
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)10.148 (2), 14.251 (3), 18.103 (4)
V3)2618.1 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.30 × 0.24 × 0.02
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.933, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
20334, 2947, 1498
Rint0.121
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.170, 0.98
No. of reflections2947
No. of parameters177
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.33

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···N10.97 (4)2.36 (3)2.675 (4)98 (2)
 

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