3-Acetyl-4-amino­quinoline

The title compound, C₁₁H₁₀N₂O, a potential anti­tumour drug, crystallizes with two mol­ecules in the asymmetric unit. The 4-amino N atom is strongly conjugated with the quinoline ring involving the 3-carbonyl group. As a result, the mol­ecule is almost planar. The amino group is involved in both intra­molecular N—H...O and inter­molecular N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.210
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON (Spek, 1992); software used to prepare material for publication: SHELXL97.

3-Acetyl-4-aminoquinoline

Crystal data

C11H10N2O	Dx = 1.358 Mg m^−3
Mr = 186.21	Melting point: 426 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 20 reflections
a = 30.815 (6) Å	θ = 7–20°
b = 8.884 (2) Å	µ = 0.09 mm^−1
c = 13.305 (3) Å	T = 296 K
V = 3642.4 (14) Å^3	Prism, yellow
Z = 16	0.30 × 0.20 × 0.15 mm
F(000) = 1568

Data collection

Oxford Difraction Gemini R CCD diffractometer	1954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.041
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω and φ scans	h = 0→39
10828 measured reflections	k = −11→11
4160 independent reflections	l = −17→17

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.210	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1154P)^2] where P = (Fo^2 + 2Fc^2)/3
4160 reflections	(Δ/σ)max = 0.003
255 parameters	Δρmax = 0.58 e Å^−3
72 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

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

18.2732 (0.0119) x - 7.1393 (0.0029) y + 0.6729 (0.0090) z = 7.7599 (0.0086)

* 0.0042 (0.0017) N1A * 0.0026 (0.0018) C2A * 0.0011 (0.0018) C3A * -0.0006 (0.0017) C4A * -0.0032 (0.0018) C5A * 0.0091 (0.0019) C6A * 0.0020 (0.0019) C7A * -0.0083 (0.0019) C8A * -0.0009 (0.0020) C9A * -0.0061 (0.0019) C10A 0.0311 (0.0029) C11A -0.0040 (0.0028) N14A

Rms deviation of fitted atoms = 0.0048

17.5837 (0.0928) x - 7.2512 (0.0194) y + 1.2046 (0.0188) z = 7.7392 (0.0415)

Angle to previous plane (with approximate e.s.d.) = 2.72 (0.35)

* 0.0000 (0.0000) C11A * 0.0000 (0.0000) O12A * 0.0000 (0.0000) C13A

Rms deviation of fitted atoms = 0.0000

18.8594 (0.0128) x - 7.0254 (0.0031) y - 0.1183 (0.0100) z = 6.9644 (0.0129)

Angle to previous plane (with approximate e.s.d.) = 6.34 (0.35)

* 0.0032 (0.0020) N1B * 0.0108 (0.0021) C2B * -0.0117 (0.0019) C3B * -0.0077 (0.0020) C4B * 0.0131 (0.0021) C5B * -0.0107 (0.0022) C6B * 0.0038 (0.0020) C7B * -0.0080 (0.0022) C8B * -0.0052 (0.0022) C9B * 0.0124 (0.0021) C10B -0.0461 (0.0035) C11B -0.0553 (0.0034) N14B

Rms deviation of fitted atoms = 0.0093

20.4498 (0.1097) x - 6.5536 (0.0265) y + 1.6519 (0.0275) z = 9.6706 (0.0792)

Angle to previous plane (with approximate e.s.d.) = 8.73 (0.43)

* 0.0000 (0.0000) C11B * 0.0000 (0.0000) O12B * 0.0000 (0.0000) C13B

Rms deviation of fitted atoms = 0.0000

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 (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.49820 (7)	0.2443 (2)	0.60074 (15)	0.0344 (5)
C2A	0.46573 (9)	0.1584 (3)	0.57123 (19)	0.0336 (6)
H2A	0.4483	0.1186	0.6216	0.040*
C3A	0.45456 (8)	0.1203 (3)	0.47153 (19)	0.0301 (5)
C4A	0.48109 (8)	0.1815 (3)	0.39309 (19)	0.0277 (5)
C5A	0.54515 (8)	0.3417 (3)	0.3503 (2)	0.0316 (6)
H5A	0.5407	0.3247	0.2821	0.038*
C6A	0.57914 (9)	0.4298 (3)	0.3812 (2)	0.0363 (6)
H6A	0.5978	0.4711	0.3336	0.044*
C7A	0.58609 (9)	0.4581 (3)	0.4818 (2)	0.0379 (6)
H7A	0.6092	0.5188	0.5014	0.045*
C8A	0.55904 (9)	0.3971 (3)	0.5534 (2)	0.0369 (6)
H8A	0.5638	0.4174	0.6210	0.044*
C9A	0.52426 (8)	0.3043 (3)	0.52487 (19)	0.0298 (5)
C10A	0.51685 (8)	0.2764 (3)	0.42142 (19)	0.0272 (5)
C11A	0.41815 (8)	0.0214 (3)	0.4493 (2)	0.0307 (6)
O12A	0.40852 (6)	−0.0161 (2)	0.36373 (14)	0.0388 (5)
C13A	0.39020 (9)	−0.0324 (3)	0.5352 (2)	0.0398 (7)
H13A	0.3673	−0.0946	0.5095	0.060*
H13B	0.3780	0.0528	0.5694	0.060*
H13C	0.4076	−0.0896	0.5813	0.060*
N14A	0.47301 (7)	0.1523 (2)	0.29715 (15)	0.0346 (6)
H14A	0.4515	0.0956	0.2810	0.041*
H14B	0.4893	0.1901	0.2511	0.041*
N1B	0.74114 (9)	0.9880 (3)	0.58896 (19)	0.0516 (6)
C2B	0.71028 (10)	0.9036 (3)	0.6225 (2)	0.0472 (7)
H2B	0.6932	0.8557	0.5745	0.057*
C3B	0.69967 (9)	0.8764 (3)	0.7228 (2)	0.0427 (6)
C4B	0.72594 (10)	0.9451 (3)	0.7975 (2)	0.0417 (6)
C5B	0.78981 (10)	1.1131 (3)	0.8287 (2)	0.0480 (7)
H5B	0.7862	1.0995	0.8975	0.058*
C6B	0.82163 (11)	1.2024 (4)	0.7964 (3)	0.0584 (8)
H6B	0.8394	1.2529	0.8418	0.070*
C7B	0.82795 (10)	1.2192 (3)	0.6907 (3)	0.0495 (7)
H7B	0.8507	1.2784	0.6675	0.059*
C8B	0.80178 (11)	1.1518 (3)	0.6244 (3)	0.0535 (8)
H8B	0.8062	1.1662	0.5559	0.064*
C9B	0.76645 (9)	1.0559 (3)	0.6588 (2)	0.0414 (6)
C10B	0.76163 (9)	1.0388 (3)	0.7622 (2)	0.0374 (6)
C11B	0.66261 (11)	0.7815 (4)	0.7511 (3)	0.0568 (8)
O12B	0.65085 (8)	0.7670 (3)	0.83945 (19)	0.0685 (7)
C13B	0.63948 (11)	0.6905 (4)	0.6767 (3)	0.0684 (10)
H13D	0.6478	0.5869	0.6838	0.103*
H13E	0.6467	0.7248	0.6104	0.103*
H13F	0.6088	0.7002	0.6871	0.103*
N14B	0.71774 (9)	0.9281 (3)	0.89539 (19)	0.0596 (8)
H14C	0.6961	0.8743	0.9146	0.071*
H14D	0.7341	0.9708	0.9392	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0355 (12)	0.0412 (13)	0.0264 (10)	0.0030 (9)	0.0006 (8)	0.0006 (10)
C2A	0.0331 (14)	0.0420 (15)	0.0259 (10)	0.0044 (10)	0.0023 (10)	0.0046 (11)
C3A	0.0339 (14)	0.0301 (13)	0.0264 (10)	0.0023 (9)	0.0009 (9)	0.0044 (10)
C4A	0.0331 (13)	0.0244 (12)	0.0257 (10)	0.0044 (9)	−0.0008 (9)	−0.0003 (10)
C5A	0.0371 (15)	0.0328 (14)	0.0250 (12)	0.0006 (10)	−0.0023 (9)	0.0029 (11)
C6A	0.0410 (15)	0.0314 (14)	0.0366 (12)	−0.0037 (11)	−0.0002 (12)	0.0074 (12)
C7A	0.0365 (15)	0.0357 (16)	0.0414 (13)	−0.0066 (11)	−0.0065 (11)	−0.0015 (12)
C8A	0.0441 (16)	0.0366 (15)	0.0300 (13)	−0.0025 (11)	−0.0072 (10)	−0.0034 (12)
C9A	0.0342 (14)	0.0278 (13)	0.0273 (10)	0.0036 (9)	−0.0030 (9)	0.0008 (11)
C10A	0.0310 (13)	0.0241 (12)	0.0264 (10)	0.0034 (9)	−0.0006 (9)	0.0002 (10)
C11A	0.0343 (14)	0.0263 (13)	0.0316 (12)	0.0065 (9)	0.0016 (10)	0.0021 (11)
O12A	0.0423 (12)	0.0379 (11)	0.0362 (9)	−0.0069 (9)	0.0012 (8)	−0.0028 (9)
C13A	0.0352 (15)	0.0432 (16)	0.0410 (13)	−0.0042 (12)	0.0028 (12)	0.0079 (14)
N14A	0.0380 (13)	0.0396 (12)	0.0261 (10)	−0.0074 (11)	0.0008 (9)	0.0025 (10)
N1B	0.0609 (16)	0.0521 (16)	0.0419 (12)	0.0082 (11)	−0.0021 (10)	0.0020 (12)
C2B	0.0531 (17)	0.0424 (17)	0.0462 (12)	0.0095 (11)	−0.0099 (12)	−0.0104 (13)
C3B	0.0365 (15)	0.0344 (15)	0.0571 (12)	0.0085 (10)	0.0003 (11)	0.0039 (13)
C4B	0.0472 (16)	0.0384 (15)	0.0395 (11)	0.0077 (10)	0.0054 (11)	0.0040 (12)
C5B	0.0470 (17)	0.0448 (17)	0.0520 (15)	0.0019 (12)	−0.0064 (12)	−0.0013 (14)
C6B	0.0512 (19)	0.0538 (19)	0.0701 (15)	−0.0038 (13)	−0.0055 (16)	0.0069 (17)
C7B	0.0385 (17)	0.0370 (16)	0.0730 (16)	0.0053 (12)	0.0059 (14)	0.0066 (15)
C8B	0.059 (2)	0.0453 (18)	0.0565 (16)	0.0034 (12)	0.0081 (13)	0.0094 (14)
C9B	0.0363 (15)	0.0437 (16)	0.0442 (12)	0.0101 (10)	0.0046 (11)	0.0060 (12)
C10B	0.0363 (14)	0.0335 (14)	0.0425 (11)	0.0103 (9)	−0.0048 (10)	0.0010 (12)
C11B	0.0473 (18)	0.0466 (18)	0.0764 (18)	0.0022 (12)	0.0062 (14)	−0.0071 (16)
O12B	0.0649 (16)	0.0548 (14)	0.0859 (16)	−0.0136 (12)	0.0252 (13)	−0.0042 (13)
C13B	0.055 (2)	0.0394 (17)	0.111 (2)	0.0077 (14)	−0.017 (2)	−0.0160 (18)
N14B	0.070 (2)	0.0594 (17)	0.0490 (12)	−0.0191 (15)	0.0031 (13)	0.0010 (13)

Geometric parameters (Å, º)

N1A—C2A	1.321 (3)	N1B—C2B	1.291 (4)
N1A—C9A	1.396 (3)	N1B—C9B	1.355 (4)
C2A—C3A	1.410 (3)	C2B—C3B	1.396 (4)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.432 (3)	C3B—C4B	1.420 (4)
C3A—C11A	1.453 (3)	C3B—C11B	1.471 (4)
C4A—N14A	1.323 (3)	C4B—N14B	1.333 (3)
C4A—C10A	1.439 (3)	C4B—C10B	1.457 (4)
C5A—C6A	1.369 (3)	C5B—C6B	1.336 (4)
C5A—C10A	1.408 (3)	C5B—C10B	1.403 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.375 (3)	C6B—C7B	1.428 (6)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.380 (3)	C7B—C8B	1.338 (4)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.408 (3)	C8B—C9B	1.456 (4)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.418 (3)	C9B—C10B	1.392 (4)
C11A—O12A	1.225 (3)	C11B—O12B	1.233 (4)
C11A—C13A	1.511 (3)	C11B—C13B	1.464 (4)
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
N14A—H14A	0.8600	N14B—H14C	0.8600
N14A—H14B	0.8600	N14B—H14D	0.8600
C2A—N1A—C9A	116.3 (2)	C2B—N1B—C9B	116.3 (2)
N1A—C2A—C3A	127.3 (2)	N1B—C2B—C3B	127.1 (3)
N1A—C2A—H2A	116.3	N1B—C2B—H2B	116.5
C3A—C2A—H2A	116.3	C3B—C2B—H2B	116.5
C2A—C3A—C4A	117.0 (2)	C2B—C3B—C4B	117.3 (2)
C2A—C3A—C11A	121.7 (2)	C2B—C3B—C11B	122.0 (3)
C4A—C3A—C11A	121.3 (2)	C4B—C3B—C11B	120.6 (3)
N14A—C4A—C3A	121.4 (2)	N14B—C4B—C3B	121.6 (3)
N14A—C4A—C10A	120.6 (2)	N14B—C4B—C10B	121.6 (3)
C3A—C4A—C10A	117.9 (2)	C3B—C4B—C10B	116.8 (2)
C6A—C5A—C10A	120.5 (2)	C6B—C5B—C10B	121.8 (3)
C6A—C5A—H5A	119.8	C6B—C5B—H5B	119.1
C10A—C5A—H5A	119.8	C10B—C5B—H5B	119.1
C5A—C6A—C7A	121.2 (2)	C5B—C6B—C7B	119.0 (3)
C5A—C6A—H6A	119.4	C5B—C6B—H6B	120.5
C7A—C6A—H6A	119.4	C7B—C6B—H6B	120.5
C6A—C7A—C8A	120.2 (2)	C8B—C7B—C6B	121.2 (3)
C6A—C7A—H7A	119.9	C8B—C7B—H7B	119.4
C8A—C7A—H7A	119.9	C6B—C7B—H7B	119.4
C7A—C8A—C9A	120.5 (2)	C7B—C8B—C9B	120.5 (3)
C7A—C8A—H8A	119.8	C7B—C8B—H8B	119.8
C9A—C8A—H8A	119.8	C9B—C8B—H8B	119.8
N1A—C9A—C8A	117.9 (2)	N1B—C9B—C10B	124.6 (3)
N1A—C9A—C10A	123.1 (2)	N1B—C9B—C8B	118.2 (3)
C8A—C9A—C10A	119.0 (2)	C10B—C9B—C8B	116.7 (3)
C5A—C10A—C9A	118.7 (2)	C9B—C10B—C5B	120.7 (3)
C5A—C10A—C4A	122.7 (2)	C9B—C10B—C4B	117.4 (2)
C9A—C10A—C4A	118.6 (2)	C5B—C10B—C4B	122.2 (2)
O12A—C11A—C3A	122.8 (2)	O12B—C11B—C13B	116.3 (3)
O12A—C11A—C13A	118.6 (2)	O12B—C11B—C3B	122.2 (3)
C3A—C11A—C13A	118.6 (2)	C13B—C11B—C3B	121.4 (3)
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C4A—N14A—H14A	120.0	C4B—N14B—H14C	120.0
C4A—N14A—H14B	120.0	C4B—N14B—H14D	120.0
H14A—N14A—H14B	120.0	H14C—N14B—H14D	120.0
C9A—N1A—C2A—C3A	0.2 (3)	C9B—N1B—C2B—C3B	1.2 (4)
N1A—C2A—C3A—C4A	−0.1 (3)	N1B—C2B—C3B—C4B	−1.8 (4)
N1A—C2A—C3A—C11A	178.5 (2)	N1B—C2B—C3B—C11B	177.9 (3)
C2A—C3A—C4A—N14A	−179.9 (2)	C2B—C3B—C4B—N14B	178.6 (2)
C11A—C3A—C4A—N14A	1.5 (3)	C11B—C3B—C4B—N14B	−1.0 (4)
C2A—C3A—C4A—C10A	−0.3 (3)	C2B—C3B—C4B—C10B	0.3 (3)
C11A—C3A—C4A—C10A	−179.1 (2)	C11B—C3B—C4B—C10B	−179.3 (2)
C10A—C5A—C6A—C7A	−0.8 (4)	C10B—C5B—C6B—C7B	−1.9 (4)
C5A—C6A—C7A—C8A	0.5 (4)	C5B—C6B—C7B—C8B	2.4 (4)
C6A—C7A—C8A—C9A	0.5 (4)	C6B—C7B—C8B—C9B	−1.4 (4)
C2A—N1A—C9A—C8A	179.6 (2)	C2B—N1B—C9B—C10B	0.9 (4)
C2A—N1A—C9A—C10A	−0.1 (3)	C2B—N1B—C9B—C8B	179.7 (2)
C7A—C8A—C9A—N1A	179.2 (2)	C7B—C8B—C9B—N1B	−179.0 (2)
C7A—C8A—C9A—C10A	−1.1 (3)	C7B—C8B—C9B—C10B	−0.1 (4)
C6A—C5A—C10A—C9A	0.2 (3)	N1B—C9B—C10B—C5B	179.4 (2)
C6A—C5A—C10A—C4A	−179.1 (2)	C8B—C9B—C10B—C5B	0.6 (4)
N1A—C9A—C10A—C5A	−179.6 (2)	N1B—C9B—C10B—C4B	−2.2 (4)
C8A—C9A—C10A—C5A	0.7 (3)	C8B—C9B—C10B—C4B	179.0 (2)
N1A—C9A—C10A—C4A	−0.3 (3)	C6B—C5B—C10B—C9B	0.4 (4)
C8A—C9A—C10A—C4A	−179.9 (2)	C6B—C5B—C10B—C4B	−177.9 (2)
N14A—C4A—C10A—C5A	−0.6 (3)	N14B—C4B—C10B—C9B	−176.9 (2)
C3A—C4A—C10A—C5A	179.8 (2)	C3B—C4B—C10B—C9B	1.4 (3)
N14A—C4A—C10A—C9A	−179.9 (2)	N14B—C4B—C10B—C5B	1.5 (4)
C3A—C4A—C10A—C9A	0.4 (3)	C3B—C4B—C10B—C5B	179.8 (2)
C2A—C3A—C11A—O12A	−178.0 (2)	C2B—C3B—C11B—O12B	−173.9 (3)
C4A—C3A—C11A—O12A	0.5 (3)	C4B—C3B—C11B—O12B	5.7 (4)
C2A—C3A—C11A—C13A	4.5 (3)	C2B—C3B—C11B—C13B	10.3 (4)
C4A—C3A—C11A—C13A	−176.9 (2)	C4B—C3B—C11B—C13B	−170.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14A—H14A···O12A	0.86	1.99	2.639 (3)	132
N14A—H14B···N1A^i	0.86	2.10	2.879 (3)	150
N14B—H14C···O12B	0.86	1.96	2.615 (3)	132
N14B—H14D···N1B^ii	0.86	2.14	2.921 (3)	151

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3/2, y, z+1/2.