N-Phenyl­quinoline-2-carboxamide

In the title compound, C₁₆H₁₂N₂O, the dihedral angle between the quinoline ring system and the phenyl ring is 6.8 (1)°. Weak N—H...N and C—H...O intra­molecular hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

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Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               1494
           Count of symmetry unique reflns         1497
           Completeness (_total/calc)             99.80%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Quinoline-2-carboxamide compounds are a class of important materials as metal ligands (Perlepes et al., 1986) and as potential radioligands for visualization of peripheral benzodiazepine receptors (Matarrese et al., 2001). We report here the crystal structure of the title compound, (I).

The O1—C11 [1.223 (3) Å], N2—C11 [1.365 (3) Å] and N2—C12 [1.412 (3) Å] bond lengths indicate extensive electron delocalization in the amide linkage. The quinoline ring system is planar within ±0.013 (2) Å. The dihedral angle between the C2/C3/C4/C9/C10/N1 and C2/C11/O1/N2 planes is 4.6 (1)° and that between C2/C11/O1/N2 and C12—C17 planes is 2.5 (1)° (Fig 1). The dihedral angle between the quinoline ring system and phenyl ring is 6.8 (1)°. Weak N—H···N and C—H···O hydrogen bonds are observed in the molecular structure (Table 1).

Related literature

For general background, see: Matarrese et al. (2001); Perlepes et al. (1986). For synthesis, see: Davis (1959).

S2. Experimental

The title compound was synthesized from 2-quinolinecarboxylic acid and aniline according to the general procedure of Davis (1959). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dimethylsulfoxide.

S3. Refinement

The N-bound H atom was located in a difference Fourier map and refined isotropically [N—H = 0.93 (3) Å]. C-bound H atoms were placed in calculated positions, with C—H = 0.95 Å, and refined using a riding model, with U_iso(H) = 1.2U_eq(C). In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement.

Computing details

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering.

N-Phenylquinoline-2-carboxamide

Crystal data

C16H12N2O	F(000) = 520
Mr = 248.28	Dx = 1.390 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8549 reflections
a = 16.9856 (19) Å	θ = 3.2–27.5°
b = 12.8279 (16) Å	µ = 0.09 mm^−1
c = 5.4455 (7) Å	T = 153 K
V = 1186.5 (3) Å^3	Plate, colourless
Z = 4	0.52 × 0.30 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1306 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.069
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −21→22
11138 measured reflections	k = −16→16
1494 independent reflections	l = −7→7

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0686P)^2] where P = (Fo^2 + 2Fc^2)/3
1494 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.20 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.

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
O1	0.28453 (9)	0.31035 (13)	0.1870 (3)	0.0383 (4)
N1	0.37707 (10)	0.43801 (13)	0.6855 (4)	0.0289 (4)
N2	0.41118 (10)	0.29930 (14)	0.3349 (4)	0.0318 (4)
C2	0.31803 (12)	0.40935 (16)	0.5420 (4)	0.0300 (5)
C3	0.24023 (13)	0.44684 (16)	0.5661 (5)	0.0346 (5)
H3	0.1996	0.4227	0.4606	0.042*
C4	0.22498 (13)	0.51849 (17)	0.7444 (5)	0.0338 (5)
H4	0.1732	0.5453	0.7639	0.041*
C5	0.27477 (13)	0.62705 (17)	1.0899 (5)	0.0340 (5)
H5	0.2241	0.6566	1.1136	0.041*
C6	0.33486 (13)	0.65688 (16)	1.2390 (5)	0.0345 (5)
H6	0.3261	0.7070	1.3645	0.041*
C7	0.41086 (13)	0.61262 (15)	1.2059 (5)	0.0333 (5)
H7	0.4530	0.6330	1.3101	0.040*
C8	0.42357 (12)	0.54080 (16)	1.0248 (5)	0.0314 (5)
H8	0.4747	0.5118	1.0052	0.038*
C9	0.36231 (11)	0.50866 (16)	0.8660 (4)	0.0276 (4)
C10	0.28592 (12)	0.55297 (16)	0.9001 (4)	0.0303 (5)
C11	0.33541 (12)	0.33470 (16)	0.3353 (4)	0.0296 (5)
C12	0.44804 (12)	0.23178 (15)	0.1655 (4)	0.0307 (5)
C13	0.52679 (12)	0.20587 (15)	0.2071 (5)	0.0331 (5)
H13	0.5536	0.2332	0.3459	0.040*
C14	0.56576 (13)	0.14009 (17)	0.0450 (5)	0.0347 (5)
H14	0.6196	0.1235	0.0722	0.042*
C15	0.52686 (13)	0.09850 (17)	−0.1561 (5)	0.0364 (5)
H15	0.5534	0.0527	−0.2652	0.044*
C16	0.44909 (15)	0.12453 (16)	−0.1958 (5)	0.0368 (5)
H16	0.4224	0.0965	−0.3341	0.044*
C17	0.40915 (13)	0.19058 (17)	−0.0381 (4)	0.0339 (5)
H17	0.3556	0.2078	−0.0684	0.041*
H2N	0.4423 (14)	0.3254 (19)	0.462 (6)	0.043 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0378 (8)	0.0424 (9)	0.0347 (9)	−0.0023 (7)	−0.0050 (8)	−0.0061 (8)
N1	0.0326 (9)	0.0263 (8)	0.0280 (9)	−0.0012 (7)	0.0010 (8)	0.0025 (8)
N2	0.0349 (9)	0.0329 (10)	0.0275 (10)	−0.0001 (8)	−0.0023 (8)	−0.0049 (9)
C2	0.0327 (10)	0.0291 (9)	0.0283 (11)	−0.0021 (9)	0.0002 (9)	0.0023 (9)
C3	0.0330 (10)	0.0372 (12)	0.0337 (12)	−0.0027 (9)	−0.0046 (10)	0.0033 (10)
C4	0.0306 (10)	0.0364 (11)	0.0343 (12)	0.0036 (9)	0.0020 (9)	0.0049 (11)
C5	0.0358 (11)	0.0335 (11)	0.0329 (12)	0.0041 (9)	0.0045 (10)	0.0025 (10)
C6	0.0438 (12)	0.0273 (10)	0.0323 (12)	0.0010 (9)	0.0061 (10)	−0.0001 (10)
C7	0.0392 (12)	0.0312 (10)	0.0295 (12)	−0.0038 (9)	−0.0011 (9)	−0.0001 (10)
C8	0.0323 (11)	0.0304 (10)	0.0316 (12)	−0.0012 (9)	0.0012 (9)	0.0029 (10)
C9	0.0321 (10)	0.0254 (9)	0.0253 (10)	−0.0008 (8)	0.0042 (9)	0.0055 (9)
C10	0.0355 (11)	0.0262 (10)	0.0292 (11)	0.0003 (8)	0.0058 (9)	0.0036 (9)
C11	0.0343 (11)	0.0273 (11)	0.0271 (11)	−0.0026 (8)	0.0020 (9)	0.0030 (9)
C12	0.0399 (11)	0.0238 (10)	0.0285 (11)	0.0000 (9)	0.0005 (10)	0.0015 (9)
C13	0.0414 (12)	0.0299 (10)	0.0282 (12)	−0.0017 (9)	−0.0033 (10)	0.0015 (10)
C14	0.0373 (11)	0.0343 (11)	0.0326 (12)	0.0030 (9)	0.0009 (10)	0.0029 (10)
C15	0.0451 (12)	0.0323 (11)	0.0319 (13)	0.0057 (10)	0.0031 (10)	−0.0003 (10)
C16	0.0460 (13)	0.0360 (11)	0.0284 (12)	0.0014 (10)	−0.0040 (10)	−0.0029 (10)
C17	0.0375 (12)	0.0333 (11)	0.0309 (13)	−0.0013 (9)	−0.0038 (9)	0.0009 (10)

Geometric parameters (Å, º)

O1—C11	1.223 (3)	C7—C8	1.367 (3)
N1—C2	1.323 (3)	C7—H7	0.95
N1—C9	1.360 (3)	C8—C9	1.415 (3)
N2—C11	1.365 (3)	C8—H8	0.95
N2—C12	1.412 (3)	C9—C10	1.429 (3)
N2—H2N	0.93 (3)	C12—C17	1.395 (3)
C2—C3	1.412 (3)	C12—C13	1.397 (3)
C2—C11	1.507 (3)	C13—C14	1.389 (3)
C3—C4	1.362 (3)	C13—H13	0.95
C3—H3	0.95	C14—C15	1.386 (3)
C4—C10	1.409 (3)	C14—H14	0.95
C4—H4	0.95	C15—C16	1.380 (3)
C5—C6	1.359 (3)	C15—H15	0.95
C5—C10	1.417 (3)	C16—C17	1.384 (3)
C5—H5	0.95	C16—H16	0.95
C6—C7	1.422 (3)	C17—H17	0.95
C6—H6	0.95
C2—N1—C9	118.18 (18)	N1—C9—C10	121.76 (19)
C11—N2—C12	128.57 (19)	C8—C9—C10	118.2 (2)
C11—N2—H2N	114.4 (15)	C4—C10—C5	123.5 (2)
C12—N2—H2N	117.0 (15)	C4—C10—C9	117.7 (2)
N1—C2—C3	124.0 (2)	C5—C10—C9	118.9 (2)
N1—C2—C11	117.99 (19)	O1—C11—N2	125.5 (2)
C3—C2—C11	117.96 (19)	O1—C11—C2	121.12 (19)
C4—C3—C2	118.3 (2)	N2—C11—C2	113.41 (19)
C4—C3—H3	120.9	C17—C12—C13	119.5 (2)
C2—C3—H3	120.9	C17—C12—N2	122.81 (19)
C3—C4—C10	120.1 (2)	C13—C12—N2	117.7 (2)
C3—C4—H4	120.0	C14—C13—C12	119.9 (2)
C10—C4—H4	120.0	C14—C13—H13	120.1
C6—C5—C10	121.6 (2)	C12—C13—H13	120.1
C6—C5—H5	119.2	C15—C14—C13	120.6 (2)
C10—C5—H5	119.2	C15—C14—H14	119.7
C5—C6—C7	119.6 (2)	C13—C14—H14	119.7
C5—C6—H6	120.2	C16—C15—C14	119.2 (2)
C7—C6—H6	120.2	C16—C15—H15	120.4
C8—C7—C6	120.3 (2)	C14—C15—H15	120.4
C8—C7—H7	119.9	C15—C16—C17	121.4 (2)
C6—C7—H7	119.9	C15—C16—H16	119.3
C7—C8—C9	121.4 (2)	C17—C16—H16	119.3
C7—C8—H8	119.3	C16—C17—C12	119.5 (2)
C9—C8—H8	119.3	C16—C17—H17	120.2
N1—C9—C8	120.03 (18)	C12—C17—H17	120.2
C9—N1—C2—C3	−0.7 (3)	N1—C9—C10—C5	−179.29 (19)
C9—N1—C2—C11	177.34 (17)	C8—C9—C10—C5	0.2 (3)
N1—C2—C3—C4	1.4 (3)	C12—N2—C11—O1	2.3 (4)
C11—C2—C3—C4	−176.62 (19)	C12—N2—C11—C2	−177.88 (19)
C2—C3—C4—C10	−0.4 (3)	N1—C2—C11—O1	−175.35 (19)
C10—C5—C6—C7	−0.4 (3)	C3—C2—C11—O1	2.8 (3)
C5—C6—C7—C8	0.2 (3)	N1—C2—C11—N2	4.8 (3)
C6—C7—C8—C9	0.1 (3)	C3—C2—C11—N2	−177.08 (19)
C2—N1—C9—C8	179.48 (19)	C11—N2—C12—C17	0.6 (3)
C2—N1—C9—C10	−1.1 (3)	C11—N2—C12—C13	−179.2 (2)
C7—C8—C9—N1	179.17 (19)	C17—C12—C13—C14	0.4 (3)
C7—C8—C9—C10	−0.3 (3)	N2—C12—C13—C14	−179.69 (19)
C3—C4—C10—C5	−179.9 (2)	C12—C13—C14—C15	−1.0 (3)
C3—C4—C10—C9	−1.2 (3)	C13—C14—C15—C16	1.0 (3)
C6—C5—C10—C4	178.8 (2)	C14—C15—C16—C17	−0.5 (3)
C6—C5—C10—C9	0.1 (3)	C15—C16—C17—C12	−0.1 (3)
N1—C9—C10—C4	2.0 (3)	C13—C12—C17—C16	0.1 (3)
C8—C9—C10—C4	−178.54 (19)	N2—C12—C17—C16	−179.76 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1	0.93 (3)	2.19 (3)	2.674 (3)	111 (2)
C17—H17···O1	0.95	2.26	2.889 (3)	123