N-(4-Methoxy­phenyl)­quinoline-2-carbox­amide

The quinolyl and phenyl rings in the title compound, C₁₇H₁₄N₂O₂, are almost coplanar. There is an intramolecular hydrogen bond between the quinoline N atom and the amide N atom [N...N = 2.6602 (17) Å and N—H...N = 112°].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.111
• Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

N-(4-methoxylphenyl)quinoline-2-carboxamide

Crystal data

C17H14N2O2	F(000) = 584
Mr = 278.30	Dx = 1.340 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.6372 (11) Å	Cell parameters from 3598 reflections
b = 18.109 (3) Å	θ = 1–27.5°
c = 11.4921 (19) Å	µ = 0.09 mm^−1
β = 92.867 (3)°	T = 294 K
V = 1379.6 (4) Å^3	Prism, colorless
Z = 4	0.38 × 0.28 × 0.26 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3167 independent reflections
Radiation source: fine-focus sealed tube	1829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.967, Tmax = 0.977	k = −13→23
9204 measured reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.15 e Å^−3
3167 reflections	Δρmin = −0.17 e Å^−3
192 parameters	Extinction correction: SHELXL97
0 restraints	Extinction coefficient: 0.020 (2)

Special details

Experimental. ? #Insert any special details here.

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	−0.13010 (18)	0.06137 (7)	0.63314 (10)	0.0686 (4)
O2	−0.56251 (18)	0.05910 (6)	0.10170 (9)	0.0650 (3)
N1	0.31035 (18)	0.16561 (6)	0.59376 (10)	0.0466 (3)
N2	−0.01159 (19)	0.11548 (7)	0.47108 (10)	0.0534 (4)
H2A	0.0896	0.1404	0.4486	0.064*
C1	−0.0033 (2)	0.09733 (9)	0.58492 (13)	0.0497 (4)
C2	0.1806 (2)	0.12669 (8)	0.65191 (12)	0.0472 (4)
C3	0.2043 (3)	0.11274 (9)	0.77225 (13)	0.0571 (4)
H3A	0.1087	0.0852	0.8098	0.068*
C4	0.3684 (3)	0.14007 (9)	0.83282 (13)	0.0585 (4)
H4A	0.3859	0.1314	0.9124	0.070*
C5	0.5122 (2)	0.18168 (8)	0.77493 (12)	0.0474 (4)
C6	0.6871 (3)	0.21201 (9)	0.83081 (14)	0.0568 (4)
H6A	0.7108	0.2054	0.9106	0.068*
C7	0.8217 (3)	0.25084 (9)	0.76933 (15)	0.0594 (4)
H7A	0.9364	0.2707	0.8072	0.071*
C8	0.7874 (2)	0.26092 (9)	0.64914 (14)	0.0567 (4)
H8A	0.8806	0.2871	0.6076	0.068*
C9	0.6202 (2)	0.23299 (9)	0.59247 (13)	0.0529 (4)
H9A	0.5992	0.2407	0.5128	0.063*
C10	0.4777 (2)	0.19233 (8)	0.65363 (12)	0.0444 (4)
C11	−0.1612 (2)	0.09970 (8)	0.38334 (12)	0.0465 (4)
C12	−0.3401 (2)	0.06309 (9)	0.40151 (13)	0.0573 (4)
H12A	−0.3680	0.0479	0.4763	0.069*
C13	−0.4776 (2)	0.04875 (9)	0.31022 (13)	0.0535 (4)
H13A	−0.5970	0.0241	0.3241	0.064*
C14	−0.4393 (2)	0.07061 (8)	0.19885 (13)	0.0483 (4)
C15	−0.2623 (3)	0.10866 (9)	0.18083 (13)	0.0566 (4)
H15A	−0.2359	0.1248	0.1063	0.068*
C16	−0.1265 (2)	0.12280 (9)	0.27108 (13)	0.0532 (4)
H16A	−0.0086	0.1484	0.2571	0.064*
C17	−0.7369 (3)	0.01502 (10)	0.11259 (15)	0.0672 (5)
H17C	−0.8058	0.0095	0.0376	0.101*
H17B	−0.8250	0.0384	0.1652	0.101*
H17A	−0.6982	−0.0327	0.1423	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0668 (8)	0.0772 (9)	0.0614 (7)	−0.0215 (7)	0.0000 (6)	0.0161 (6)
O2	0.0701 (8)	0.0750 (8)	0.0486 (6)	−0.0187 (6)	−0.0096 (5)	0.0058 (6)
N1	0.0496 (8)	0.0464 (8)	0.0436 (7)	−0.0002 (6)	0.0006 (6)	−0.0021 (6)
N2	0.0535 (8)	0.0591 (9)	0.0475 (8)	−0.0127 (6)	0.0023 (6)	0.0004 (6)
C1	0.0532 (10)	0.0462 (9)	0.0497 (9)	−0.0001 (8)	0.0028 (8)	0.0022 (7)
C2	0.0508 (9)	0.0428 (9)	0.0480 (9)	0.0039 (7)	0.0022 (7)	0.0009 (7)
C3	0.0614 (11)	0.0606 (11)	0.0492 (9)	−0.0020 (8)	0.0027 (8)	0.0099 (8)
C4	0.0696 (11)	0.0641 (11)	0.0413 (8)	0.0043 (9)	−0.0042 (8)	0.0081 (8)
C5	0.0543 (10)	0.0424 (9)	0.0450 (8)	0.0066 (7)	−0.0022 (7)	0.0004 (7)
C6	0.0659 (11)	0.0537 (10)	0.0494 (9)	0.0051 (9)	−0.0123 (8)	0.0009 (8)
C7	0.0569 (10)	0.0550 (10)	0.0644 (11)	0.0008 (8)	−0.0138 (8)	−0.0045 (9)
C8	0.0538 (10)	0.0556 (10)	0.0605 (10)	−0.0028 (8)	0.0005 (8)	−0.0024 (8)
C9	0.0564 (10)	0.0562 (10)	0.0456 (8)	−0.0010 (8)	0.0001 (7)	−0.0012 (7)
C10	0.0484 (9)	0.0405 (9)	0.0439 (8)	0.0050 (7)	−0.0011 (7)	−0.0025 (7)
C11	0.0509 (9)	0.0434 (9)	0.0451 (8)	−0.0039 (7)	0.0019 (7)	−0.0031 (7)
C12	0.0613 (10)	0.0674 (11)	0.0433 (8)	−0.0152 (9)	0.0049 (8)	0.0043 (8)
C13	0.0522 (10)	0.0563 (10)	0.0519 (9)	−0.0118 (8)	0.0022 (7)	0.0033 (8)
C14	0.0558 (10)	0.0430 (9)	0.0458 (9)	−0.0011 (7)	−0.0002 (7)	0.0007 (7)
C15	0.0667 (11)	0.0595 (11)	0.0435 (9)	−0.0124 (9)	0.0034 (8)	0.0080 (8)
C16	0.0554 (10)	0.0520 (10)	0.0525 (9)	−0.0129 (8)	0.0067 (8)	0.0031 (8)
C17	0.0570 (11)	0.0759 (13)	0.0680 (11)	−0.0075 (9)	−0.0055 (9)	−0.0038 (9)

Geometric parameters (Å, º)

O1—C1	1.2190 (17)	C7—H7A	0.9300
O2—C14	1.3664 (17)	C8—C9	1.356 (2)
O2—C17	1.417 (2)	C8—H8A	0.9300
N1—C2	1.3199 (18)	C9—C10	1.413 (2)
N1—C10	1.3655 (18)	C9—H9A	0.9300
N2—C1	1.3474 (19)	C11—C12	1.385 (2)
N2—C11	1.4085 (18)	C11—C16	1.387 (2)
N2—H2A	0.8600	C12—C13	1.380 (2)
C1—C2	1.507 (2)	C12—H12A	0.9300
C2—C3	1.407 (2)	C13—C14	1.375 (2)
C3—C4	1.356 (2)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.386 (2)
C4—C5	1.409 (2)	C15—C16	1.364 (2)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.409 (2)	C16—H16A	0.9300
C5—C10	1.4146 (19)	C17—H17C	0.9600
C6—C7	1.362 (2)	C17—H17B	0.9600
C6—H6A	0.9300	C17—H17A	0.9600
C7—C8	1.400 (2)
C14—O2—C17	118.16 (12)	C8—C9—H9A	119.8
C2—N1—C10	117.95 (12)	C10—C9—H9A	119.8
C1—N2—C11	129.69 (13)	N1—C10—C9	118.80 (13)
C1—N2—H2A	115.2	N1—C10—C5	122.41 (14)
C11—N2—H2A	115.2	C9—C10—C5	118.79 (14)
O1—C1—N2	125.17 (14)	C12—C11—C16	117.93 (14)
O1—C1—C2	121.08 (14)	C12—C11—N2	124.63 (13)
N2—C1—C2	113.74 (14)	C16—C11—N2	117.44 (14)
N1—C2—C3	123.37 (14)	C13—C12—C11	120.98 (14)
N1—C2—C1	117.51 (13)	C13—C12—H12A	119.5
C3—C2—C1	119.11 (14)	C11—C12—H12A	119.5
C4—C3—C2	119.09 (15)	C14—C13—C12	120.48 (15)
C4—C3—H3A	120.5	C14—C13—H13A	119.8
C2—C3—H3A	120.5	C12—C13—H13A	119.8
C3—C4—C5	119.90 (14)	O2—C14—C13	125.85 (14)
C3—C4—H4A	120.1	O2—C14—C15	115.50 (13)
C5—C4—H4A	120.1	C13—C14—C15	118.64 (14)
C4—C5—C6	123.73 (14)	C16—C15—C14	120.84 (14)
C4—C5—C10	117.25 (14)	C16—C15—H15A	119.6
C6—C5—C10	119.01 (15)	C14—C15—H15A	119.6
C7—C6—C5	120.76 (14)	C15—C16—C11	121.10 (15)
C7—C6—H6A	119.6	C15—C16—H16A	119.5
C5—C6—H6A	119.6	C11—C16—H16A	119.5
C6—C7—C8	120.04 (15)	O2—C17—H17C	109.5
C6—C7—H7A	120.0	O2—C17—H17B	109.5
C8—C7—H7A	120.0	H17C—C17—H17B	109.5
C9—C8—C7	120.90 (16)	O2—C17—H17A	109.5
C9—C8—H8A	119.6	H17C—C17—H17A	109.5
C7—C8—H8A	119.6	H17B—C17—H17A	109.5
C8—C9—C10	120.49 (14)
C11—N2—C1—O1	1.1 (3)	C8—C9—C10—N1	179.46 (14)
C11—N2—C1—C2	−178.19 (14)	C8—C9—C10—C5	0.3 (2)
C10—N1—C2—C3	1.3 (2)	C4—C5—C10—N1	1.7 (2)
C10—N1—C2—C1	−179.88 (12)	C6—C5—C10—N1	−178.98 (13)
O1—C1—C2—N1	−179.50 (14)	C4—C5—C10—C9	−179.19 (14)
N2—C1—C2—N1	−0.2 (2)	C6—C5—C10—C9	0.1 (2)
O1—C1—C2—C3	−0.6 (2)	C1—N2—C11—C12	2.9 (3)
N2—C1—C2—C3	178.66 (14)	C1—N2—C11—C16	−177.34 (15)
N1—C2—C3—C4	−0.3 (2)	C16—C11—C12—C13	1.3 (2)
C1—C2—C3—C4	−179.05 (14)	N2—C11—C12—C13	−178.94 (15)
C2—C3—C4—C5	−0.1 (2)	C11—C12—C13—C14	0.0 (3)
C3—C4—C5—C6	−179.87 (15)	C17—O2—C14—C13	−6.2 (2)
C3—C4—C5—C10	−0.6 (2)	C17—O2—C14—C15	174.59 (14)
C4—C5—C6—C7	179.05 (15)	C12—C13—C14—O2	179.44 (15)
C10—C5—C6—C7	−0.2 (2)	C12—C13—C14—C15	−1.4 (2)
C5—C6—C7—C8	−0.1 (2)	O2—C14—C15—C16	−179.33 (14)
C6—C7—C8—C9	0.6 (2)	C13—C14—C15—C16	1.4 (2)
C7—C8—C9—C10	−0.7 (2)	C14—C15—C16—C11	−0.1 (3)
C2—N1—C10—C9	178.85 (13)	C12—C11—C16—C15	−1.3 (2)
C2—N1—C10—C5	−2.0 (2)	N2—C11—C16—C15	178.95 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.21	2.6602 (17)	112