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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°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022419/ac6024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022419/ac6024Isup2.hkl
Contains datablock I

CCDC reference: 203021

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








Computing details top

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 top
Crystal data top
C16H11IN2OF(000) = 728
Mr = 374.17Dx = 1.798 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.5389 (10) ÅCell parameters from 4725 reflections
b = 17.036 (3) Åθ = 1–27.5°
c = 12.702 (2) ŵ = 2.31 mm1
β = 102.377 (3)°T = 294 K
V = 1382.1 (4) Å3PRISM, yellow
Z = 40.20 × 0.18 × 0.14 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3169 independent reflections
Radiation source: fine-focus sealed tube2153 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.6°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 86
Tmin = 0.655, Tmax = 0.738k = 2220
9337 measured reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3169 reflectionsΔρmax = 0.61 e Å3
181 parametersΔρmin = 0.33 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
I10.73626 (3)0.085146 (15)0.107807 (18)0.06689 (11)
O11.3784 (3)0.09556 (13)0.57661 (18)0.0635 (6)
N11.8030 (3)0.18297 (13)0.49117 (17)0.0428 (5)
N21.4644 (4)0.09772 (13)0.4118 (2)0.0496 (6)
H2A1.56060.11370.38020.060*
C12.1005 (4)0.25189 (18)0.4569 (2)0.0508 (7)
H1B2.06720.23500.38560.061*
C22.2703 (5)0.29842 (19)0.4910 (3)0.0592 (8)
H2B2.35190.31310.44260.071*
C32.3244 (5)0.3245 (2)0.5969 (3)0.0652 (9)
H3A2.44080.35670.61850.078*
C42.2069 (5)0.3031 (2)0.6701 (3)0.0601 (9)
H4A2.24480.32020.74110.072*
C52.0284 (4)0.25515 (16)0.6368 (2)0.0464 (7)
C61.8986 (5)0.23214 (19)0.7061 (2)0.0553 (8)
H6A1.92910.24830.77770.066*
C71.7287 (5)0.18645 (19)0.6688 (2)0.0548 (8)
H7A1.64190.17090.71410.066*
C81.6867 (4)0.16315 (16)0.5600 (2)0.0431 (7)
C91.9747 (4)0.22898 (15)0.5286 (2)0.0416 (7)
C101.4944 (4)0.11484 (17)0.5182 (2)0.0460 (7)
C111.2966 (4)0.05721 (17)0.3460 (2)0.0444 (7)
C121.1149 (4)0.03794 (19)0.3795 (2)0.0520 (8)
H12A1.09910.05210.44800.062*
C130.9566 (4)0.00244 (18)0.3107 (3)0.0522 (8)
H13A0.83480.01550.33340.063*
C140.9787 (4)0.02331 (17)0.2092 (2)0.0477 (7)
C151.1588 (4)0.00457 (18)0.1749 (2)0.0525 (8)
H15A1.17340.01850.10610.063*
C161.3173 (4)0.03514 (18)0.2436 (3)0.0522 (8)
H16A1.43970.04730.22100.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04726 (15)0.07677 (19)0.07553 (18)0.00761 (10)0.01072 (11)0.01366 (12)
O10.0546 (14)0.0793 (18)0.0611 (14)0.0157 (11)0.0226 (11)0.0117 (11)
N10.0412 (13)0.0420 (14)0.0462 (13)0.0016 (11)0.0117 (11)0.0049 (11)
N20.0432 (14)0.0498 (16)0.0606 (16)0.0103 (11)0.0220 (12)0.0016 (12)
C10.0485 (18)0.0525 (19)0.0518 (17)0.0044 (15)0.0118 (14)0.0009 (15)
C20.0471 (19)0.056 (2)0.078 (2)0.0073 (15)0.0206 (17)0.0050 (17)
C30.0461 (19)0.053 (2)0.094 (3)0.0045 (15)0.0096 (19)0.0084 (19)
C40.052 (2)0.059 (2)0.064 (2)0.0013 (15)0.0013 (16)0.0141 (17)
C50.0436 (17)0.0430 (17)0.0505 (17)0.0073 (13)0.0052 (14)0.0016 (14)
C60.060 (2)0.061 (2)0.0445 (17)0.0036 (16)0.0104 (15)0.0044 (15)
C70.057 (2)0.062 (2)0.0493 (18)0.0031 (16)0.0204 (15)0.0032 (16)
C80.0406 (16)0.0390 (16)0.0503 (17)0.0055 (12)0.0112 (13)0.0064 (13)
C90.0394 (16)0.0354 (16)0.0494 (16)0.0037 (12)0.0083 (13)0.0044 (12)
C100.0422 (16)0.0420 (17)0.0550 (18)0.0041 (13)0.0132 (14)0.0069 (14)
C110.0384 (16)0.0401 (16)0.0574 (18)0.0023 (12)0.0162 (14)0.0010 (14)
C120.0459 (18)0.057 (2)0.0576 (19)0.0044 (14)0.0211 (15)0.0012 (15)
C130.0397 (17)0.055 (2)0.065 (2)0.0044 (14)0.0197 (15)0.0068 (15)
C140.0396 (16)0.0454 (18)0.0588 (19)0.0005 (12)0.0122 (14)0.0023 (14)
C150.0467 (18)0.056 (2)0.0572 (19)0.0017 (14)0.0179 (15)0.0046 (15)
C160.0417 (17)0.053 (2)0.068 (2)0.0011 (14)0.0252 (15)0.0006 (16)
Geometric parameters (Å, º) top
I1—C142.099 (3)C5—C91.416 (4)
O1—C101.215 (3)C6—C71.356 (4)
N1—C81.320 (3)C6—H6A0.9300
N1—C91.368 (3)C7—C81.407 (4)
N2—C101.355 (4)C7—H7A0.9300
N2—C111.409 (4)C8—C101.502 (4)
N2—H2A0.8600C11—C121.384 (4)
C1—C21.357 (4)C11—C161.388 (4)
C1—C91.407 (4)C12—C131.385 (4)
C1—H1B0.9300C12—H12A0.9300
C2—C31.388 (5)C13—C141.375 (4)
C2—H2B0.9300C13—H13A0.9300
C3—C41.376 (5)C14—C151.378 (4)
C3—H3A0.9300C15—C161.381 (4)
C4—C51.413 (4)C15—H15A0.9300
C4—H4A0.9300C16—H16A0.9300
C5—C61.403 (4)
C8—N1—C9117.6 (2)N1—C8—C10117.6 (3)
C10—N2—C11128.7 (2)C7—C8—C10118.3 (3)
C10—N2—H2A115.7N1—C9—C1119.0 (2)
C11—N2—H2A115.7N1—C9—C5122.1 (2)
C2—C1—C9120.4 (3)C1—C9—C5118.9 (3)
C2—C1—H1B119.8O1—C10—N2125.1 (3)
C9—C1—H1B119.8O1—C10—C8121.1 (3)
C1—C2—C3121.2 (3)N2—C10—C8113.7 (3)
C1—C2—H2B119.4C12—C11—C16119.1 (3)
C3—C2—H2B119.4C12—C11—N2123.0 (3)
C4—C3—C2120.4 (3)C16—C11—N2117.9 (3)
C4—C3—H3A119.8C11—C12—C13119.9 (3)
C2—C3—H3A119.8C11—C12—H12A120.1
C3—C4—C5119.7 (3)C13—C12—H12A120.1
C3—C4—H4A120.1C14—C13—C12120.3 (3)
C5—C4—H4A120.1C14—C13—H13A119.8
C6—C5—C4123.1 (3)C12—C13—H13A119.8
C6—C5—C9117.6 (3)C13—C14—C15120.4 (3)
C4—C5—C9119.3 (3)C13—C14—I1119.2 (2)
C7—C6—C5120.1 (3)C15—C14—I1120.4 (2)
C7—C6—H6A119.9C14—C15—C16119.3 (3)
C5—C6—H6A119.9C14—C15—H15A120.3
C6—C7—C8118.5 (3)C16—C15—H15A120.3
C6—C7—H7A120.7C15—C16—C11121.0 (3)
C8—C7—H7A120.7C15—C16—H16A119.5
N1—C8—C7124.0 (3)C11—C16—H16A119.5
C9—C1—C2—C30.0 (5)C4—C5—C9—C10.3 (4)
C1—C2—C3—C40.5 (5)C11—N2—C10—O11.8 (5)
C2—C3—C4—C50.9 (5)C11—N2—C10—C8176.7 (3)
C3—C4—C5—C6178.7 (3)N1—C8—C10—O1178.8 (3)
C3—C4—C5—C90.8 (4)C7—C8—C10—O10.7 (4)
C4—C5—C6—C7179.5 (3)N1—C8—C10—N20.3 (4)
C9—C5—C6—C70.0 (4)C7—C8—C10—N2177.9 (3)
C5—C6—C7—C80.1 (5)C10—N2—C11—C1210.0 (5)
C9—N1—C8—C70.0 (4)C10—N2—C11—C16169.2 (3)
C9—N1—C8—C10178.1 (2)C16—C11—C12—C130.4 (5)
C6—C7—C8—N10.1 (5)N2—C11—C12—C13179.6 (3)
C6—C7—C8—C10178.0 (3)C11—C12—C13—C140.2 (5)
C8—N1—C9—C1179.3 (2)C12—C13—C14—C150.2 (5)
C8—N1—C9—C50.1 (4)C12—C13—C14—I1179.6 (2)
C2—C1—C9—N1179.1 (3)C13—C14—C15—C160.3 (5)
C2—C1—C9—C50.1 (4)I1—C14—C15—C16179.1 (2)
C6—C5—C9—N10.1 (4)C14—C15—C16—C110.8 (5)
C4—C5—C9—N1179.4 (3)C12—C11—C16—C150.9 (5)
C6—C5—C9—C1179.2 (3)N2—C11—C16—C15179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.862.222.659 (3)112
 

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