Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014325/bt6079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014325/bt6079Isup2.hkl |
CCDC reference: 175371
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.090
- Data-to-parameter ratio = 12.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.54 From the CIF: _reflns_number_total 2371 Count of symmetry unique reflns 1753 Completeness (_total/calc) 135.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 618 Fraction of Friedel pairs measured 0.353 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
The title compound was synthesized from 2-quinolinecarboxylic acid and (D)-α-methylbenzylamine according to the general procedure of Johnson et al. (1960). Therefore, the absolute configuration of the chiral centre was known in advance as R. The crystal used for the data collection was obtained by slow evaporation from a saturated DMF-water (10:1) solution at room temperature.
The C-bound H atoms were placed at geometrically calculated positions and included in the final refinement using the riding-model approximation.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.
Fig. 1. The molecular structure of (I) showing ellipsoids plotted at the 30% probability level (Siemens, 1995). |
C18H16N2O | ? # Insert any comments here. |
Mr = 276.33 | Dx = 1.270 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5955 (11) Å | Cell parameters from 2871 reflections |
b = 10.684 (2) Å | θ = 1–27.5° |
c = 12.224 (2) Å | µ = 0.08 mm−1 |
β = 98.687 (4)° | T = 294 K |
V = 722.4 (2) Å3 | Plate, colourless |
Z = 2 | 0.28 × 0.20 × 0.10 mm |
F(000) = 292 |
Bruker CCD area-detector diffractometer | 2371 independent reflections |
Radiation source: fine-focus sealed tube | 1768 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.978, Tmax = 0.992 | k = −13→9 |
4900 measured reflections | l = −15→15 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2371 reflections | Δρmax = 0.11 e Å−3 |
190 parameters | Δρmin = −0.12 e Å−3 |
C18H16N2O | V = 722.4 (2) Å3 |
Mr = 276.33 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.5955 (11) Å | µ = 0.08 mm−1 |
b = 10.684 (2) Å | T = 294 K |
c = 12.224 (2) Å | 0.28 × 0.20 × 0.10 mm |
β = 98.687 (4)° |
Bruker CCD area-detector diffractometer | 2371 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1768 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.992 | Rint = 0.023 |
4900 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 1 restraint |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.11 e Å−3 |
2371 reflections | Δρmin = −0.12 e Å−3 |
190 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.3133 (3) | 0.21680 (16) | 0.12833 (12) | 0.0691 (5) | |
N1 | 0.0831 (3) | 0.17179 (18) | 0.14073 (12) | 0.0542 (4) | |
H1A | 0.2258 | 0.1858 | 0.1756 | 0.065* | |
N2 | 0.1586 (3) | 0.30859 (15) | 0.33384 (12) | 0.0465 (4) | |
C1 | 0.2094 (4) | 0.2274 (2) | −0.08681 (17) | 0.0574 (6) | |
H1B | 0.3449 | 0.2421 | −0.0343 | 0.069* | |
C2 | 0.1906 (4) | 0.2847 (2) | −0.18824 (17) | 0.0637 (6) | |
H2B | 0.3127 | 0.3381 | −0.2035 | 0.076* | |
C3 | −0.0063 (4) | 0.2639 (2) | −0.26704 (17) | 0.0661 (7) | |
H3A | −0.0177 | 0.3021 | −0.3360 | 0.079* | |
C4 | −0.1863 (4) | 0.1864 (3) | −0.24348 (18) | 0.0673 (7) | |
H4A | −0.3213 | 0.1723 | −0.2965 | 0.081* | |
C5 | −0.1688 (4) | 0.1289 (2) | −0.14121 (17) | 0.0574 (6) | |
H5A | −0.2924 | 0.0766 | −0.1259 | 0.069* | |
C6 | 0.0308 (3) | 0.1486 (2) | −0.06166 (16) | 0.0482 (5) | |
C7 | 0.0540 (4) | 0.0823 (2) | 0.04895 (16) | 0.0523 (5) | |
H7A | −0.0960 | 0.0357 | 0.0513 | 0.063* | |
C8 | 0.2611 (4) | −0.0106 (2) | 0.06516 (19) | 0.0647 (6) | |
H8A | 0.2677 | −0.0505 | 0.1359 | 0.097* | |
H8B | 0.4104 | 0.0325 | 0.0621 | 0.097* | |
H8C | 0.2363 | −0.0727 | 0.0078 | 0.097* | |
C9 | −0.1031 (4) | 0.2323 (2) | 0.17215 (15) | 0.0508 (5) | |
C10 | −0.0475 (3) | 0.32209 (19) | 0.26686 (14) | 0.0469 (5) | |
C11 | −0.2200 (4) | 0.4130 (2) | 0.28159 (18) | 0.0583 (6) | |
H11A | −0.3639 | 0.4182 | 0.2326 | 0.070* | |
C12 | −0.1752 (4) | 0.4929 (2) | 0.36763 (18) | 0.0623 (6) | |
H12A | −0.2862 | 0.5553 | 0.3770 | 0.075* | |
C13 | 0.0400 (4) | 0.48168 (19) | 0.44329 (16) | 0.0513 (5) | |
C14 | 0.0995 (5) | 0.5604 (2) | 0.53617 (19) | 0.0661 (6) | |
H14A | −0.0067 | 0.6234 | 0.5499 | 0.079* | |
C15 | 0.3104 (5) | 0.5447 (2) | 0.60535 (19) | 0.0687 (7) | |
H15A | 0.3499 | 0.5981 | 0.6654 | 0.082* | |
C16 | 0.4681 (4) | 0.4490 (2) | 0.58715 (17) | 0.0649 (6) | |
H16A | 0.6107 | 0.4381 | 0.6362 | 0.078* | |
C17 | 0.4169 (4) | 0.3713 (2) | 0.49884 (15) | 0.0555 (5) | |
H17A | 0.5240 | 0.3075 | 0.4881 | 0.067* | |
C18 | 0.2032 (3) | 0.38675 (18) | 0.42357 (14) | 0.0445 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0534 (9) | 0.0819 (12) | 0.0688 (9) | −0.0096 (8) | −0.0011 (7) | −0.0087 (8) |
N1 | 0.0500 (10) | 0.0606 (11) | 0.0497 (9) | −0.0063 (9) | −0.0004 (7) | −0.0070 (8) |
N2 | 0.0524 (10) | 0.0451 (9) | 0.0422 (8) | 0.0002 (8) | 0.0079 (7) | 0.0011 (7) |
C1 | 0.0482 (11) | 0.0664 (15) | 0.0545 (12) | −0.0076 (11) | −0.0025 (9) | −0.0008 (11) |
C2 | 0.0587 (13) | 0.0697 (16) | 0.0627 (13) | −0.0059 (12) | 0.0093 (11) | 0.0039 (12) |
C3 | 0.0702 (15) | 0.0755 (17) | 0.0514 (12) | 0.0165 (14) | 0.0056 (11) | 0.0032 (11) |
C4 | 0.0548 (13) | 0.0873 (18) | 0.0541 (12) | 0.0071 (13) | −0.0098 (10) | −0.0132 (12) |
C5 | 0.0460 (11) | 0.0662 (16) | 0.0582 (13) | −0.0048 (11) | 0.0014 (10) | −0.0121 (11) |
C6 | 0.0435 (10) | 0.0485 (12) | 0.0513 (10) | −0.0002 (9) | 0.0033 (8) | −0.0112 (9) |
C7 | 0.0509 (12) | 0.0511 (12) | 0.0526 (11) | −0.0097 (10) | 0.0006 (9) | −0.0064 (10) |
C8 | 0.0715 (14) | 0.0521 (14) | 0.0679 (13) | 0.0006 (12) | 0.0017 (11) | 0.0022 (11) |
C9 | 0.0547 (12) | 0.0529 (12) | 0.0436 (10) | −0.0075 (10) | 0.0027 (9) | 0.0070 (9) |
C10 | 0.0493 (11) | 0.0475 (12) | 0.0440 (10) | −0.0044 (10) | 0.0074 (9) | 0.0105 (9) |
C11 | 0.0542 (12) | 0.0623 (15) | 0.0565 (12) | 0.0044 (12) | 0.0026 (9) | 0.0056 (11) |
C12 | 0.0617 (14) | 0.0560 (14) | 0.0699 (14) | 0.0146 (12) | 0.0123 (11) | 0.0037 (13) |
C13 | 0.0612 (13) | 0.0445 (12) | 0.0486 (11) | 0.0022 (10) | 0.0096 (9) | 0.0032 (9) |
C14 | 0.0826 (17) | 0.0525 (15) | 0.0642 (14) | 0.0110 (12) | 0.0143 (12) | −0.0083 (12) |
C15 | 0.0865 (17) | 0.0639 (16) | 0.0540 (13) | −0.0018 (14) | 0.0054 (12) | −0.0146 (11) |
C16 | 0.0642 (14) | 0.0781 (16) | 0.0497 (13) | 0.0017 (13) | −0.0005 (10) | −0.0061 (11) |
C17 | 0.0563 (12) | 0.0615 (14) | 0.0472 (10) | 0.0072 (11) | 0.0025 (10) | −0.0047 (10) |
C18 | 0.0498 (11) | 0.0428 (11) | 0.0421 (10) | −0.0033 (9) | 0.0104 (8) | 0.0028 (9) |
O1—C9 | 1.227 (2) | C8—H8A | 0.9600 |
N1—C9 | 1.331 (3) | C8—H8B | 0.9600 |
N1—C7 | 1.464 (3) | C8—H8C | 0.9600 |
N1—H1A | 0.8600 | C9—C10 | 1.500 (3) |
N2—C10 | 1.317 (2) | C10—C11 | 1.400 (3) |
N2—C18 | 1.371 (2) | C11—C12 | 1.349 (3) |
C1—C2 | 1.372 (3) | C11—H11A | 0.9300 |
C1—C6 | 1.377 (3) | C12—C13 | 1.408 (3) |
C1—H1B | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.368 (3) | C13—C18 | 1.410 (3) |
C2—H2B | 0.9300 | C13—C14 | 1.412 (3) |
C3—C4 | 1.368 (4) | C14—C15 | 1.354 (3) |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—C5 | 1.383 (3) | C15—C16 | 1.390 (3) |
C4—H4A | 0.9300 | C15—H15A | 0.9300 |
C5—C6 | 1.382 (3) | C16—C17 | 1.357 (3) |
C5—H5A | 0.9300 | C16—H16A | 0.9300 |
C6—C7 | 1.514 (3) | C17—C18 | 1.404 (3) |
C7—C8 | 1.516 (3) | C17—H17A | 0.9300 |
C7—H7A | 0.9800 | ||
C9—N1—C7 | 122.48 (16) | H8A—C8—H8C | 109.5 |
C9—N1—H1A | 118.8 | H8B—C8—H8C | 109.5 |
C7—N1—H1A | 118.8 | O1—C9—N1 | 123.29 (19) |
C10—N2—C18 | 117.84 (17) | O1—C9—C10 | 119.8 (2) |
C2—C1—C6 | 121.02 (19) | N1—C9—C10 | 116.95 (17) |
C2—C1—H1B | 119.5 | N2—C10—C11 | 123.49 (19) |
C6—C1—H1B | 119.5 | N2—C10—C9 | 118.02 (18) |
C3—C2—C1 | 120.5 (2) | C11—C10—C9 | 118.46 (18) |
C3—C2—H2B | 119.8 | C12—C11—C10 | 119.3 (2) |
C1—C2—H2B | 119.8 | C12—C11—H11A | 120.4 |
C4—C3—C2 | 119.4 (2) | C10—C11—H11A | 120.4 |
C4—C3—H3A | 120.3 | C11—C12—C13 | 119.9 (2) |
C2—C3—H3A | 120.3 | C11—C12—H12A | 120.1 |
C3—C4—C5 | 120.4 (2) | C13—C12—H12A | 120.1 |
C3—C4—H4A | 119.8 | C12—C13—C18 | 117.44 (18) |
C5—C4—H4A | 119.8 | C12—C13—C14 | 123.5 (2) |
C6—C5—C4 | 120.5 (2) | C18—C13—C14 | 119.09 (18) |
C6—C5—H5A | 119.7 | C15—C14—C13 | 120.4 (2) |
C4—C5—H5A | 119.7 | C15—C14—H14A | 119.8 |
C1—C6—C5 | 118.22 (19) | C13—C14—H14A | 119.8 |
C1—C6—C7 | 121.19 (17) | C14—C15—C16 | 120.4 (2) |
C5—C6—C7 | 120.58 (19) | C14—C15—H15A | 119.8 |
N1—C7—C6 | 111.31 (17) | C16—C15—H15A | 119.8 |
N1—C7—C8 | 109.47 (16) | C17—C16—C15 | 120.9 (2) |
C6—C7—C8 | 112.57 (18) | C17—C16—H16A | 119.5 |
N1—C7—H7A | 107.8 | C15—C16—H16A | 119.5 |
C6—C7—H7A | 107.8 | C16—C17—C18 | 120.4 (2) |
C8—C7—H7A | 107.8 | C16—C17—H17A | 119.8 |
C7—C8—H8A | 109.5 | C18—C17—H17A | 119.8 |
C7—C8—H8B | 109.5 | N2—C18—C17 | 119.15 (18) |
H8A—C8—H8B | 109.5 | N2—C18—C13 | 122.04 (16) |
C7—C8—H8C | 109.5 | C17—C18—C13 | 118.81 (17) |
Experimental details
Crystal data | |
Chemical formula | C18H16N2O |
Mr | 276.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 5.5955 (11), 10.684 (2), 12.224 (2) |
β (°) | 98.687 (4) |
V (Å3) | 722.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.978, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4900, 2371, 1768 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.090, 0.96 |
No. of reflections | 2371 |
No. of parameters | 190 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.12 |
Computer programs: SMART (Siemens, 1995), SMART, SHELXTL-NT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT.
Recently, we have reported the structure of the tridentate ligand N,N'-di-2-naphthylpyridine-2,6-dicarboxamide (Qi et al., 2001). Because the steric effect, the bulky naphthyl ring will hinder the coordination of the ligand to a metal ion, so a new chiral bidentate ligand, (I), containing the quinoline-2-carboxamide stem was synthesized. It is estimated that the N atom of the quinoline ring and the amide N atom will coordinate to a metal ion and form a complex with a five-membered ring structure. The quinolyl and phenyl rings in (I) (Fig. 1) are not coplanar, and form a dihedral angle of 89.07 (5)°. The amide group is rotated out of the quinoline ring plane, forming a dihedral angle of 21.19 (1)°. The title compound could have practical applications as a new chiral ligand (Noyori, 1989).