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

The quinolyl and phenyl rings in the title compound, C₁₆H₁₁IN₂O, are almost coplanar. There is an intramolecular hydrogen bond between the quinoline N atom and amide N atom [N...N = 2.659 (3) Å and N—H...N = 112°].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.072
• Data-to-parameter ratio = 17.5

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-iodopheny)quinoline-2-carboxamide

Crystal data

C16H11IN2O	F(000) = 728
Mr = 374.17	Dx = 1.798 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.5389 (10) Å	Cell parameters from 4725 reflections
b = 17.036 (3) Å	θ = 1–27.5°
c = 12.702 (2) Å	µ = 2.31 mm^−1
β = 102.377 (3)°	T = 294 K
V = 1382.1 (4) Å^3	PRISM, yellow
Z = 4	0.20 × 0.18 × 0.14 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3169 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −8→6
Tmin = 0.655, Tmax = 0.738	k = −22→20
9337 measured reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3169 reflections	Δρmax = 0.61 e Å^−3
181 parameters	Δρmin = −0.33 e Å^−3

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
I1	0.73626 (3)	0.085146 (15)	0.107807 (18)	0.06689 (11)
O1	1.3784 (3)	−0.09556 (13)	0.57661 (18)	0.0635 (6)
N1	1.8030 (3)	−0.18297 (13)	0.49117 (17)	0.0428 (5)
N2	1.4644 (4)	−0.09772 (13)	0.4118 (2)	0.0496 (6)
H2A	1.5606	−0.1137	0.3802	0.060*
C1	2.1005 (4)	−0.25189 (18)	0.4569 (2)	0.0508 (7)
H1B	2.0672	−0.2350	0.3856	0.061*
C2	2.2703 (5)	−0.29842 (19)	0.4910 (3)	0.0592 (8)
H2B	2.3519	−0.3131	0.4426	0.071*
C3	2.3244 (5)	−0.3245 (2)	0.5969 (3)	0.0652 (9)
H3A	2.4408	−0.3567	0.6185	0.078*
C4	2.2069 (5)	−0.3031 (2)	0.6701 (3)	0.0601 (9)
H4A	2.2448	−0.3202	0.7411	0.072*
C5	2.0284 (4)	−0.25515 (16)	0.6368 (2)	0.0464 (7)
C6	1.8986 (5)	−0.23214 (19)	0.7061 (2)	0.0553 (8)
H6A	1.9291	−0.2483	0.7777	0.066*
C7	1.7287 (5)	−0.18645 (19)	0.6688 (2)	0.0548 (8)
H7A	1.6419	−0.1709	0.7141	0.066*
C8	1.6867 (4)	−0.16315 (16)	0.5600 (2)	0.0431 (7)
C9	1.9747 (4)	−0.22898 (15)	0.5286 (2)	0.0416 (7)
C10	1.4944 (4)	−0.11484 (17)	0.5182 (2)	0.0460 (7)
C11	1.2966 (4)	−0.05721 (17)	0.3460 (2)	0.0444 (7)
C12	1.1149 (4)	−0.03794 (19)	0.3795 (2)	0.0520 (8)
H12A	1.0991	−0.0521	0.4480	0.062*
C13	0.9566 (4)	0.00244 (18)	0.3107 (3)	0.0522 (8)
H13A	0.8348	0.0155	0.3334	0.063*
C14	0.9787 (4)	0.02331 (17)	0.2092 (2)	0.0477 (7)
C15	1.1588 (4)	0.00457 (18)	0.1749 (2)	0.0525 (8)
H15A	1.1734	0.0185	0.1061	0.063*
C16	1.3173 (4)	−0.03514 (18)	0.2436 (3)	0.0522 (8)
H16A	1.4397	−0.0473	0.2210	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04726 (15)	0.07677 (19)	0.07553 (18)	0.00761 (10)	0.01072 (11)	0.01366 (12)
O1	0.0546 (14)	0.0793 (18)	0.0611 (14)	0.0157 (11)	0.0226 (11)	−0.0117 (11)
N1	0.0412 (13)	0.0420 (14)	0.0462 (13)	−0.0016 (11)	0.0117 (11)	−0.0049 (11)
N2	0.0432 (14)	0.0498 (16)	0.0606 (16)	0.0103 (11)	0.0220 (12)	0.0016 (12)
C1	0.0485 (18)	0.0525 (19)	0.0518 (17)	0.0044 (15)	0.0118 (14)	−0.0009 (15)
C2	0.0471 (19)	0.056 (2)	0.078 (2)	0.0073 (15)	0.0206 (17)	−0.0050 (17)
C3	0.0461 (19)	0.053 (2)	0.094 (3)	0.0045 (15)	0.0096 (19)	0.0084 (19)
C4	0.052 (2)	0.059 (2)	0.064 (2)	−0.0013 (15)	−0.0013 (16)	0.0141 (17)
C5	0.0436 (17)	0.0430 (17)	0.0505 (17)	−0.0073 (13)	0.0052 (14)	−0.0016 (14)
C6	0.060 (2)	0.061 (2)	0.0445 (17)	−0.0036 (16)	0.0104 (15)	0.0044 (15)
C7	0.057 (2)	0.062 (2)	0.0493 (18)	−0.0031 (16)	0.0204 (15)	−0.0032 (16)
C8	0.0406 (16)	0.0390 (16)	0.0503 (17)	−0.0055 (12)	0.0112 (13)	−0.0064 (13)
C9	0.0394 (16)	0.0354 (16)	0.0494 (16)	−0.0037 (12)	0.0083 (13)	−0.0044 (12)
C10	0.0422 (16)	0.0420 (17)	0.0550 (18)	−0.0041 (13)	0.0132 (14)	−0.0069 (14)
C11	0.0384 (16)	0.0401 (16)	0.0574 (18)	0.0023 (12)	0.0162 (14)	−0.0010 (14)
C12	0.0459 (18)	0.057 (2)	0.0576 (19)	0.0044 (14)	0.0211 (15)	0.0012 (15)
C13	0.0397 (17)	0.055 (2)	0.065 (2)	0.0044 (14)	0.0197 (15)	−0.0068 (15)
C14	0.0396 (16)	0.0454 (18)	0.0588 (19)	−0.0005 (12)	0.0122 (14)	−0.0023 (14)
C15	0.0467 (18)	0.056 (2)	0.0572 (19)	−0.0017 (14)	0.0179 (15)	0.0046 (15)
C16	0.0417 (17)	0.053 (2)	0.068 (2)	0.0011 (14)	0.0252 (15)	−0.0006 (16)

Geometric parameters (Å, º)

I1—C14	2.099 (3)	C5—C9	1.416 (4)
O1—C10	1.215 (3)	C6—C7	1.356 (4)
N1—C8	1.320 (3)	C6—H6A	0.9300
N1—C9	1.368 (3)	C7—C8	1.407 (4)
N2—C10	1.355 (4)	C7—H7A	0.9300
N2—C11	1.409 (4)	C8—C10	1.502 (4)
N2—H2A	0.8600	C11—C12	1.384 (4)
C1—C2	1.357 (4)	C11—C16	1.388 (4)
C1—C9	1.407 (4)	C12—C13	1.385 (4)
C1—H1B	0.9300	C12—H12A	0.9300
C2—C3	1.388 (5)	C13—C14	1.375 (4)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.376 (5)	C14—C15	1.378 (4)
C3—H3A	0.9300	C15—C16	1.381 (4)
C4—C5	1.413 (4)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.403 (4)
C8—N1—C9	117.6 (2)	N1—C8—C10	117.6 (3)
C10—N2—C11	128.7 (2)	C7—C8—C10	118.3 (3)
C10—N2—H2A	115.7	N1—C9—C1	119.0 (2)
C11—N2—H2A	115.7	N1—C9—C5	122.1 (2)
C2—C1—C9	120.4 (3)	C1—C9—C5	118.9 (3)
C2—C1—H1B	119.8	O1—C10—N2	125.1 (3)
C9—C1—H1B	119.8	O1—C10—C8	121.1 (3)
C1—C2—C3	121.2 (3)	N2—C10—C8	113.7 (3)
C1—C2—H2B	119.4	C12—C11—C16	119.1 (3)
C3—C2—H2B	119.4	C12—C11—N2	123.0 (3)
C4—C3—C2	120.4 (3)	C16—C11—N2	117.9 (3)
C4—C3—H3A	119.8	C11—C12—C13	119.9 (3)
C2—C3—H3A	119.8	C11—C12—H12A	120.1
C3—C4—C5	119.7 (3)	C13—C12—H12A	120.1
C3—C4—H4A	120.1	C14—C13—C12	120.3 (3)
C5—C4—H4A	120.1	C14—C13—H13A	119.8
C6—C5—C4	123.1 (3)	C12—C13—H13A	119.8
C6—C5—C9	117.6 (3)	C13—C14—C15	120.4 (3)
C4—C5—C9	119.3 (3)	C13—C14—I1	119.2 (2)
C7—C6—C5	120.1 (3)	C15—C14—I1	120.4 (2)
C7—C6—H6A	119.9	C14—C15—C16	119.3 (3)
C5—C6—H6A	119.9	C14—C15—H15A	120.3
C6—C7—C8	118.5 (3)	C16—C15—H15A	120.3
C6—C7—H7A	120.7	C15—C16—C11	121.0 (3)
C8—C7—H7A	120.7	C15—C16—H16A	119.5
N1—C8—C7	124.0 (3)	C11—C16—H16A	119.5
C9—C1—C2—C3	0.0 (5)	C4—C5—C9—C1	0.3 (4)
C1—C2—C3—C4	−0.5 (5)	C11—N2—C10—O1	−1.8 (5)
C2—C3—C4—C5	0.9 (5)	C11—N2—C10—C8	176.7 (3)
C3—C4—C5—C6	178.7 (3)	N1—C8—C10—O1	178.8 (3)
C3—C4—C5—C9	−0.8 (4)	C7—C8—C10—O1	0.7 (4)
C4—C5—C6—C7	−179.5 (3)	N1—C8—C10—N2	0.3 (4)
C9—C5—C6—C7	0.0 (4)	C7—C8—C10—N2	−177.9 (3)
C5—C6—C7—C8	0.1 (5)	C10—N2—C11—C12	−10.0 (5)
C9—N1—C8—C7	0.0 (4)	C10—N2—C11—C16	169.2 (3)
C9—N1—C8—C10	−178.1 (2)	C16—C11—C12—C13	0.4 (5)
C6—C7—C8—N1	−0.1 (5)	N2—C11—C12—C13	179.6 (3)
C6—C7—C8—C10	178.0 (3)	C11—C12—C13—C14	0.2 (5)
C8—N1—C9—C1	179.3 (2)	C12—C13—C14—C15	−0.2 (5)
C8—N1—C9—C5	0.1 (4)	C12—C13—C14—I1	−179.6 (2)
C2—C1—C9—N1	−179.1 (3)	C13—C14—C15—C16	−0.3 (5)
C2—C1—C9—C5	0.1 (4)	I1—C14—C15—C16	179.1 (2)
C6—C5—C9—N1	−0.1 (4)	C14—C15—C16—C11	0.8 (5)
C4—C5—C9—N1	179.4 (3)	C12—C11—C16—C15	−0.9 (5)
C6—C5—C9—C1	−179.2 (3)	N2—C11—C16—C15	179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.22	2.659 (3)	112