(E)-1-(2-Thienyl)­ethanone 8-quinolyl­hydro­zone

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

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


 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

---

S1. Comment

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) ų. 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.

S2. Experimental

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

S3. Refinement

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 R_int value (>0.10) may be due to a slight missalignment of the crystal plate on the diffractometer with respect to the beam.

Computing details

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

Fig. 1. The molecular configuration and atom numbering scheme for (I), showing 30% probability ellipsoids.

(E)-1-(2-Thienyl)ethanone 8-quinolylhydrozone

Crystal data

C15H13N3S	Dx = 1.357 Mg m^−3
Mr = 267.34	Melting point: 432-434 K K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.148 (2) Å	Cell parameters from 46446 reflections
b = 14.251 (3) Å	θ = 1.0–27.5°
c = 18.103 (4) Å	µ = 0.24 mm^−1
V = 2618.1 (9) Å^3	T = 150 K
Z = 8	Plate, orange
F(000) = 1120	0.30 × 0.24 × 0.02 mm

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2947 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1498 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.121
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
ϕ and ω scans	h = −11→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −18→18
Tmin = 0.933, Tmax = 0.995	l = −23→21
20334 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0867P)^2] where P = (Fo^2 + 2Fc^2)/3
2947 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.5693 (2)	0.64109 (18)	0.37293 (13)	0.0418 (7)
C2	0.6529 (3)	0.7026 (2)	0.35234 (16)	0.0381 (8)
H2	0.6626	0.7562	0.3831	0.048*
C3	0.7324 (3)	0.6993 (2)	0.28868 (19)	0.0494 (9)
H3	0.7920	0.7485	0.2768	0.062*
C4	0.7195 (3)	0.6214 (2)	0.24448 (17)	0.0471 (9)
H4	0.7712	0.6154	0.2010	0.059*
C5	0.6099 (3)	0.4681 (2)	0.22149 (17)	0.0433 (8)
H5	0.6582	0.4583	0.1772	0.054*
C6	0.5212 (3)	0.4034 (2)	0.24518 (18)	0.0462 (8)
H6	0.5088	0.3480	0.2168	0.058*
C7	0.4480 (3)	0.4150 (2)	0.30912 (16)	0.0403 (8)
H7	0.3864	0.3683	0.3235	0.050*
C8	0.4644 (3)	0.4946 (2)	0.35212 (15)	0.0357 (7)
C9	0.5564 (3)	0.5637 (2)	0.32874 (16)	0.0369 (7)
C10	0.6294 (3)	0.5505 (2)	0.26396 (16)	0.0387 (8)
N11	0.3944 (3)	0.5114 (2)	0.41531 (14)	0.0417 (7)
H11	0.414 (3)	0.564 (3)	0.4480 (18)	0.065 (11)*
N12	0.3027 (2)	0.44926 (17)	0.43975 (14)	0.0371 (6)
C13	0.2338 (3)	0.4690 (2)	0.49707 (16)	0.0354 (7)
C14	0.2482 (3)	0.5580 (2)	0.54076 (16)	0.0417 (8)
H141	0.3407	0.5664	0.5548	0.052*
H142	0.1936	0.5542	0.5853	0.052*
H143	0.2196	0.6113	0.5106	0.052*
S15	0.10862 (8)	0.30193 (6)	0.46517 (4)	0.0436 (3)
C16	0.1370 (3)	0.4000 (2)	0.51981 (15)	0.0333 (7)
C17	0.0599 (3)	0.3978 (2)	0.58123 (17)	0.0448 (8)
H17	0.0597	0.4455	0.6179	0.056*
C18	−0.0204 (3)	0.3163 (2)	0.58454 (18)	0.0475 (9)
H18	−0.0793	0.3032	0.6240	0.059*
C19	−0.0041 (3)	0.2597 (2)	0.52583 (16)	0.0432 (8)
H19	−0.0505	0.2024	0.5191	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0371 (16)	0.0437 (17)	0.0447 (15)	0.0006 (13)	−0.0044 (12)	−0.0032 (13)
C2	0.0367 (18)	0.0368 (19)	0.0409 (18)	0.0009 (15)	0.0032 (15)	0.0027 (13)
C3	0.0344 (19)	0.051 (2)	0.063 (2)	−0.0020 (16)	−0.0026 (17)	0.0130 (17)
C4	0.0285 (18)	0.067 (3)	0.0457 (19)	0.0109 (17)	0.0083 (15)	0.0128 (17)
C5	0.0369 (19)	0.055 (2)	0.0381 (18)	0.0110 (16)	0.0035 (15)	0.0017 (15)
C6	0.0389 (19)	0.048 (2)	0.051 (2)	0.0077 (17)	−0.0023 (16)	−0.0037 (16)
C7	0.0333 (18)	0.046 (2)	0.0420 (18)	0.0024 (15)	−0.0013 (15)	0.0016 (15)
C8	0.0278 (17)	0.0418 (19)	0.0374 (17)	0.0035 (14)	−0.0045 (14)	0.0054 (14)
C9	0.0267 (17)	0.045 (2)	0.0387 (17)	0.0071 (15)	−0.0033 (14)	0.0033 (14)
C10	0.0291 (18)	0.047 (2)	0.0397 (19)	0.0063 (14)	0.0009 (14)	0.0114 (14)
N11	0.0401 (16)	0.0489 (17)	0.0361 (15)	−0.0052 (13)	0.0044 (13)	−0.0028 (13)
N12	0.0324 (14)	0.0371 (15)	0.0418 (15)	−0.0018 (12)	0.0000 (12)	0.0068 (11)
C13	0.0315 (17)	0.0408 (19)	0.0337 (17)	0.0046 (14)	−0.0046 (14)	0.0041 (13)
C14	0.0421 (19)	0.0374 (18)	0.0456 (19)	−0.0008 (14)	−0.0036 (15)	−0.0022 (14)
S15	0.0419 (5)	0.0418 (5)	0.0470 (5)	−0.0019 (4)	0.0060 (4)	−0.0015 (3)
C16	0.0277 (17)	0.0350 (17)	0.0371 (17)	0.0041 (13)	−0.0045 (13)	0.0036 (12)
C17	0.043 (2)	0.048 (2)	0.0434 (19)	0.0026 (16)	0.0062 (15)	0.0001 (15)
C18	0.040 (2)	0.054 (2)	0.048 (2)	−0.0023 (17)	0.0051 (15)	0.0054 (16)
C19	0.0346 (18)	0.0404 (19)	0.055 (2)	0.0003 (15)	0.0046 (15)	0.0030 (15)

Geometric parameters (Å, º)

N1—C2	1.276 (4)	C9—C10	1.400 (4)
N1—C9	1.369 (4)	N11—N12	1.359 (3)
C2—C3	1.407 (4)	N11—H11	0.97 (4)
C2—H2	0.9500	N12—C13	1.283 (4)
C3—C4	1.375 (5)	C13—C16	1.449 (4)
C3—H3	0.9500	C13—C14	1.501 (4)
C4—C10	1.406 (4)	C14—H141	0.9800
C4—H4	0.9500	C14—H142	0.9800
C5—C6	1.359 (4)	C14—H143	0.9800
C5—C10	1.418 (4)	S15—C19	1.696 (3)
C5—H5	0.9500	S15—C16	1.736 (3)
C6—C7	1.385 (4)	C16—C17	1.360 (4)
C6—H6	0.9500	C17—C18	1.420 (4)
C7—C8	1.386 (4)	C17—H17	0.9500
C7—H7	0.9500	C18—C19	1.345 (4)
C8—N11	1.368 (4)	C18—H18	0.9500
C8—C9	1.421 (4)	C19—H19	0.9500
C2—N1—C9	116.5 (3)	C4—C10—C5	123.3 (3)
N1—C2—C3	126.7 (3)	N12—N11—C8	121.0 (3)
N1—C2—H2	116.7	N12—N11—H11	116 (2)
C3—C2—H2	116.7	C8—N11—H11	123 (2)
C4—C3—C2	116.7 (3)	C13—N12—N11	119.6 (3)
C4—C3—H3	121.7	N12—C13—C16	116.7 (3)
C2—C3—H3	121.7	N12—C13—C14	124.0 (3)
C3—C4—C10	119.7 (3)	C16—C13—C14	119.3 (3)
C3—C4—H4	120.1	C13—C14—H141	109.5
C10—C4—H4	120.1	C13—C14—H142	109.5
C6—C5—C10	118.9 (3)	H141—C14—H142	109.5
C6—C5—H5	120.5	C13—C14—H143	109.5
C10—C5—H5	120.5	H141—C14—H143	109.5
C5—C6—C7	122.5 (3)	H142—C14—H143	109.5
C5—C6—H6	118.7	C19—S15—C16	91.66 (15)
C7—C6—H6	118.7	C17—C16—C13	129.6 (3)
C6—C7—C8	120.2 (3)	C17—C16—S15	110.6 (2)
C6—C7—H7	119.9	C13—C16—S15	119.8 (2)
C8—C7—H7	119.9	C16—C17—C18	112.6 (3)
N11—C8—C7	123.4 (3)	C16—C17—H17	123.7
N11—C8—C9	118.0 (3)	C18—C17—H17	123.7
C7—C8—C9	118.6 (3)	C19—C18—C17	112.8 (3)
N1—C9—C10	123.2 (3)	C19—C18—H18	123.6
N1—C9—C8	116.5 (3)	C17—C18—H18	123.6
C10—C9—C8	120.3 (3)	C18—C19—S15	112.4 (3)
C9—C10—C4	117.3 (3)	C18—C19—H19	123.8
C9—C10—C5	119.4 (3)	S15—C19—H19	123.8
C9—N1—C2—C3	0.5 (5)	C6—C5—C10—C9	−0.5 (4)
N1—C2—C3—C4	−0.7 (5)	C6—C5—C10—C4	179.6 (3)
C2—C3—C4—C10	0.4 (4)	C7—C8—N11—N12	0.0 (4)
C10—C5—C6—C7	0.4 (5)	C9—C8—N11—N12	178.5 (2)
C5—C6—C7—C8	−0.5 (5)	C8—N11—N12—C13	−176.5 (3)
C6—C7—C8—N11	179.1 (3)	N11—N12—C13—C16	179.5 (2)
C6—C7—C8—C9	0.6 (4)	N11—N12—C13—C14	−0.5 (4)
C2—N1—C9—C10	−0.1 (4)	N12—C13—C16—C17	173.2 (3)
C2—N1—C9—C8	179.3 (3)	C14—C13—C16—C17	−6.7 (4)
N11—C8—C9—N1	1.4 (4)	N12—C13—C16—S15	−5.9 (3)
C7—C8—C9—N1	180.0 (3)	C14—C13—C16—S15	174.1 (2)
N11—C8—C9—C10	−179.2 (3)	C19—S15—C16—C17	−0.6 (2)
C7—C8—C9—C10	−0.6 (4)	C19—S15—C16—C13	178.7 (2)
N1—C9—C10—C4	−0.1 (4)	C13—C16—C17—C18	−178.3 (3)
C8—C9—C10—C4	−179.5 (2)	S15—C16—C17—C18	0.9 (3)
N1—C9—C10—C5	179.9 (3)	C16—C17—C18—C19	−0.9 (4)
C8—C9—C10—C5	0.6 (4)	C17—C18—C19—S15	0.4 (4)
C3—C4—C10—C9	0.0 (4)	C16—S15—C19—C18	0.1 (3)
C3—C4—C10—C5	179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N1	0.97 (4)	2.36 (3)	2.675 (4)	98 (2)