Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022453/nc2032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022453/nc2032Isup2.hkl |
CCDC reference: 651451
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.124
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 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
Compound (I) was prepared according to the method of Yang et al. (2006). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvent from an ethanol-water (4:1 v/v) solution over a period of 3 d.
The H atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.2 Ueq(C) using a riding model with C—H distances of 0.93 Å.
As part of our ongoing studies on push-pull Schiff bases, the title compound was synthesized and its crystal structure was determined (Yang et al., 2006).
The molecule is almost planar with a dihedral angle of 3.67 (1)° between the two aromatic rings (Fig. 1). As expected, the bond lengths between the benzene and naphthalene rings in (I) alternates. In the crystal structure the molecules are stacked onto each other with distances of 3.782 and 3.731 Å between the centroids of the rings, indicating for π-π interactions.
For related literature, see: Yang et al. (2006).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Fig. 1. Crystal structure of I showing 50% probability displacement ellipsoids and the atom numbering scheme. |
C19H14N2O2 | F(000) = 632 |
Mr = 302.32 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.440 (2) Å | Cell parameters from 1605 reflections |
b = 7.4165 (10) Å | θ = 2.8–23.8° |
c = 14.598 (2) Å | µ = 0.09 mm−1 |
β = 117.347 (2)° | T = 293 K |
V = 1484.7 (3) Å3 | Plate, yellow |
Z = 4 | 0.42 × 0.26 × 0.05 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 2913 independent reflections |
Radiation source: fine-focus sealed tube | 2014 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 1.5° |
ω scans | h = −19→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→8 |
Tmin = 0.964, Tmax = 0.996 | l = −18→17 |
8073 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0855P] where P = (Fo2 + 2Fc2)/3 |
2913 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C19H14N2O2 | V = 1484.7 (3) Å3 |
Mr = 302.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.440 (2) Å | µ = 0.09 mm−1 |
b = 7.4165 (10) Å | T = 293 K |
c = 14.598 (2) Å | 0.42 × 0.26 × 0.05 mm |
β = 117.347 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 2913 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2014 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.996 | Rint = 0.039 |
8073 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.13 e Å−3 |
2913 reflections | Δρmin = −0.20 e Å−3 |
208 parameters |
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 | ||
C19 | 0.18422 (11) | 0.8023 (2) | 0.42612 (12) | 0.0389 (4) | |
C6 | −0.25313 (11) | 0.6242 (2) | 0.47210 (13) | 0.0413 (4) | |
N2 | 0.02462 (10) | 0.7772 (2) | 0.41815 (11) | 0.0487 (4) | |
N1 | −0.40204 (11) | 0.5240 (2) | 0.31629 (12) | 0.0548 (4) | |
C5 | −0.35316 (11) | 0.5882 (2) | 0.42333 (12) | 0.0420 (4) | |
C10 | 0.08469 (11) | 0.7471 (2) | 0.37018 (13) | 0.0417 (4) | |
C1 | −0.21576 (13) | 0.6856 (2) | 0.57357 (14) | 0.0504 (5) | |
H1A | −0.1493 | 0.7096 | 0.6101 | 0.061* | |
C7 | −0.18684 (11) | 0.5971 (2) | 0.42695 (13) | 0.0466 (4) | |
H7A | −0.1989 | 0.5005 | 0.3821 | 0.056* | |
C11 | 0.05107 (13) | 0.6791 (2) | 0.27212 (14) | 0.0519 (5) | |
H11A | −0.0135 | 0.6421 | 0.2361 | 0.062* | |
C14 | 0.24596 (11) | 0.7850 (2) | 0.37904 (13) | 0.0424 (4) | |
C4 | −0.41129 (13) | 0.6127 (2) | 0.47087 (15) | 0.0518 (5) | |
H4A | −0.4775 | 0.5865 | 0.4358 | 0.062* | |
C13 | 0.20743 (13) | 0.7164 (3) | 0.27765 (14) | 0.0523 (5) | |
H13A | 0.2475 | 0.7066 | 0.2459 | 0.063* | |
C9 | −0.04464 (12) | 0.6684 (2) | 0.40303 (14) | 0.0494 (5) | |
H9A | −0.0528 | 0.5655 | 0.3635 | 0.059* | |
C12 | 0.11219 (13) | 0.6645 (3) | 0.22567 (14) | 0.0553 (5) | |
H12A | 0.0879 | 0.6192 | 0.1590 | 0.066* | |
C18 | 0.22384 (12) | 0.8694 (2) | 0.52798 (13) | 0.0458 (4) | |
H18A | 0.1839 | 0.8819 | 0.5596 | 0.055* | |
C17 | 0.31968 (13) | 0.9160 (2) | 0.58045 (14) | 0.0525 (5) | |
H17A | 0.3446 | 0.9597 | 0.6475 | 0.063* | |
C2 | −0.27333 (15) | 0.7122 (3) | 0.62153 (15) | 0.0582 (5) | |
H2B | −0.2458 | 0.7547 | 0.6890 | 0.070* | |
C15 | 0.34514 (12) | 0.8360 (2) | 0.43613 (15) | 0.0509 (5) | |
H15A | 0.3865 | 0.8264 | 0.4059 | 0.061* | |
C16 | 0.38070 (13) | 0.8985 (2) | 0.53407 (15) | 0.0553 (5) | |
H16A | 0.4462 | 0.9299 | 0.5706 | 0.066* | |
O2 | −0.47769 (10) | 0.4391 (2) | 0.28762 (11) | 0.0802 (5) | |
O1 | −0.36607 (10) | 0.5584 (3) | 0.25959 (10) | 0.0848 (5) | |
C8 | −0.11034 (12) | 0.7017 (2) | 0.44595 (14) | 0.0493 (5) | |
H8A | −0.0989 | 0.8009 | 0.4890 | 0.059* | |
C3 | −0.37129 (15) | 0.6760 (3) | 0.57018 (16) | 0.0585 (5) | |
H3A | −0.4103 | 0.6943 | 0.6025 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C19 | 0.0397 (9) | 0.0348 (9) | 0.0434 (9) | 0.0039 (7) | 0.0203 (8) | 0.0073 (7) |
C6 | 0.0381 (9) | 0.0376 (9) | 0.0486 (10) | 0.0023 (7) | 0.0203 (8) | 0.0062 (7) |
N2 | 0.0363 (8) | 0.0543 (9) | 0.0576 (9) | 0.0043 (7) | 0.0233 (7) | 0.0046 (7) |
N1 | 0.0438 (9) | 0.0663 (10) | 0.0467 (9) | 0.0024 (8) | 0.0142 (8) | 0.0057 (8) |
C5 | 0.0391 (9) | 0.0423 (9) | 0.0437 (9) | 0.0014 (7) | 0.0183 (8) | 0.0049 (8) |
C10 | 0.0359 (9) | 0.0431 (10) | 0.0463 (10) | 0.0052 (7) | 0.0192 (8) | 0.0074 (8) |
C1 | 0.0442 (10) | 0.0497 (11) | 0.0519 (11) | −0.0041 (8) | 0.0173 (9) | −0.0010 (8) |
C7 | 0.0403 (10) | 0.0476 (10) | 0.0532 (10) | 0.0030 (8) | 0.0225 (8) | 0.0034 (8) |
C11 | 0.0397 (10) | 0.0581 (11) | 0.0484 (10) | −0.0003 (8) | 0.0122 (8) | 0.0065 (9) |
C14 | 0.0409 (9) | 0.0413 (10) | 0.0469 (10) | 0.0042 (7) | 0.0218 (8) | 0.0086 (8) |
C4 | 0.0443 (10) | 0.0515 (11) | 0.0659 (12) | −0.0009 (8) | 0.0306 (10) | 0.0038 (9) |
C13 | 0.0552 (11) | 0.0605 (12) | 0.0500 (11) | 0.0076 (9) | 0.0317 (9) | 0.0065 (9) |
C9 | 0.0381 (9) | 0.0499 (11) | 0.0596 (11) | 0.0067 (8) | 0.0218 (9) | 0.0063 (9) |
C12 | 0.0564 (12) | 0.0661 (13) | 0.0422 (10) | 0.0027 (9) | 0.0215 (9) | 0.0013 (9) |
C18 | 0.0492 (10) | 0.0444 (10) | 0.0471 (10) | −0.0002 (8) | 0.0249 (9) | 0.0023 (8) |
C17 | 0.0521 (11) | 0.0508 (11) | 0.0471 (10) | −0.0059 (8) | 0.0163 (9) | 0.0005 (9) |
C2 | 0.0704 (13) | 0.0532 (12) | 0.0553 (11) | −0.0028 (10) | 0.0325 (10) | −0.0055 (9) |
C15 | 0.0421 (10) | 0.0518 (11) | 0.0645 (12) | 0.0020 (8) | 0.0293 (9) | 0.0115 (9) |
C16 | 0.0394 (10) | 0.0531 (11) | 0.0640 (12) | −0.0076 (8) | 0.0155 (9) | 0.0065 (9) |
O2 | 0.0538 (9) | 0.1017 (12) | 0.0619 (9) | −0.0247 (8) | 0.0067 (7) | −0.0022 (8) |
O1 | 0.0686 (10) | 0.1381 (16) | 0.0511 (8) | −0.0080 (9) | 0.0304 (8) | −0.0017 (9) |
C8 | 0.0392 (10) | 0.0510 (11) | 0.0589 (11) | 0.0057 (8) | 0.0235 (9) | 0.0062 (9) |
C3 | 0.0675 (13) | 0.0547 (12) | 0.0711 (13) | 0.0005 (9) | 0.0472 (11) | −0.0016 (10) |
C19—C18 | 1.413 (2) | C14—C15 | 1.418 (2) |
C19—C14 | 1.414 (2) | C4—C3 | 1.371 (3) |
C19—C10 | 1.429 (2) | C4—H4A | 0.9300 |
C6—C1 | 1.396 (2) | C13—C12 | 1.364 (2) |
C6—C5 | 1.398 (2) | C13—H13A | 0.9300 |
C6—C7 | 1.464 (2) | C9—C8 | 1.438 (2) |
N2—C9 | 1.275 (2) | C9—H9A | 0.9300 |
N2—C10 | 1.413 (2) | C12—H12A | 0.9300 |
N1—O1 | 1.2171 (18) | C18—C17 | 1.362 (2) |
N1—O2 | 1.2192 (18) | C18—H18A | 0.9300 |
N1—C5 | 1.468 (2) | C17—C16 | 1.396 (2) |
C5—C4 | 1.376 (2) | C17—H17A | 0.9300 |
C10—C11 | 1.375 (2) | C2—C3 | 1.371 (3) |
C1—C2 | 1.375 (2) | C2—H2B | 0.9300 |
C1—H1A | 0.9300 | C15—C16 | 1.356 (3) |
C7—C8 | 1.331 (2) | C15—H15A | 0.9300 |
C7—H7A | 0.9300 | C16—H16A | 0.9300 |
C11—C12 | 1.396 (2) | C8—H8A | 0.9300 |
C11—H11A | 0.9300 | C3—H3A | 0.9300 |
C14—C13 | 1.412 (2) | ||
C18—C19—C14 | 118.73 (15) | C12—C13—C14 | 120.81 (17) |
C18—C19—C10 | 122.28 (15) | C12—C13—H13A | 119.6 |
C14—C19—C10 | 118.96 (15) | C14—C13—H13A | 119.6 |
C1—C6—C5 | 115.11 (15) | N2—C9—C8 | 121.30 (18) |
C1—C6—C7 | 119.26 (15) | N2—C9—H9A | 119.3 |
C5—C6—C7 | 125.60 (16) | C8—C9—H9A | 119.3 |
C9—N2—C10 | 120.23 (16) | C13—C12—C11 | 120.28 (17) |
O1—N1—O2 | 122.65 (17) | C13—C12—H12A | 119.9 |
O1—N1—C5 | 118.92 (15) | C11—C12—H12A | 119.9 |
O2—N1—C5 | 118.43 (16) | C17—C18—C19 | 120.97 (16) |
C4—C5—C6 | 122.82 (16) | C17—C18—H18A | 119.5 |
C4—C5—N1 | 116.38 (15) | C19—C18—H18A | 119.5 |
C6—C5—N1 | 120.79 (15) | C18—C17—C16 | 120.30 (17) |
C11—C10—N2 | 123.64 (15) | C18—C17—H17A | 119.9 |
C11—C10—C19 | 119.50 (15) | C16—C17—H17A | 119.9 |
N2—C10—C19 | 116.74 (15) | C3—C2—C1 | 120.16 (19) |
C2—C1—C6 | 122.55 (17) | C3—C2—H2B | 119.9 |
C2—C1—H1A | 118.7 | C1—C2—H2B | 119.9 |
C6—C1—H1A | 118.7 | C16—C15—C14 | 121.05 (17) |
C8—C7—C6 | 124.28 (17) | C16—C15—H15A | 119.5 |
C8—C7—H7A | 117.9 | C14—C15—H15A | 119.5 |
C6—C7—H7A | 117.9 | C15—C16—C17 | 120.43 (16) |
C10—C11—C12 | 121.18 (16) | C15—C16—H16A | 119.8 |
C10—C11—H11A | 119.4 | C17—C16—H16A | 119.8 |
C12—C11—H11A | 119.4 | C7—C8—C9 | 123.05 (18) |
C13—C14—C19 | 119.25 (15) | C7—C8—H8A | 118.5 |
C13—C14—C15 | 122.24 (16) | C9—C8—H8A | 118.5 |
C19—C14—C15 | 118.51 (16) | C2—C3—C4 | 119.54 (18) |
C3—C4—C5 | 119.81 (17) | C2—C3—H3A | 120.2 |
C3—C4—H4A | 120.1 | C4—C3—H3A | 120.2 |
C5—C4—H4A | 120.1 | ||
C1—C6—C5—C4 | 0.6 (2) | C18—C19—C14—C15 | −0.1 (2) |
C7—C6—C5—C4 | 178.47 (15) | C10—C19—C14—C15 | −178.49 (14) |
C1—C6—C5—N1 | 179.58 (15) | C6—C5—C4—C3 | 0.4 (3) |
C7—C6—C5—N1 | −2.5 (3) | N1—C5—C4—C3 | −178.66 (16) |
O1—N1—C5—C4 | 154.51 (17) | C19—C14—C13—C12 | −1.0 (3) |
O2—N1—C5—C4 | −25.0 (2) | C15—C14—C13—C12 | 178.42 (16) |
O1—N1—C5—C6 | −24.5 (2) | C10—N2—C9—C8 | −176.27 (14) |
O2—N1—C5—C6 | 155.98 (16) | C14—C13—C12—C11 | 0.2 (3) |
C9—N2—C10—C11 | 36.7 (2) | C10—C11—C12—C13 | 0.6 (3) |
C9—N2—C10—C19 | −147.33 (16) | C14—C19—C18—C17 | −0.3 (2) |
C18—C19—C10—C11 | −178.51 (16) | C10—C19—C18—C17 | 178.06 (15) |
C14—C19—C10—C11 | −0.2 (2) | C19—C18—C17—C16 | 0.1 (3) |
C18—C19—C10—N2 | 5.3 (2) | C6—C1—C2—C3 | 0.8 (3) |
C14—C19—C10—N2 | −176.33 (14) | C13—C14—C15—C16 | −178.85 (17) |
C5—C6—C1—C2 | −1.2 (2) | C19—C14—C15—C16 | 0.6 (2) |
C7—C6—C1—C2 | −179.20 (16) | C14—C15—C16—C17 | −0.8 (3) |
C1—C6—C7—C8 | −36.3 (2) | C18—C17—C16—C15 | 0.4 (3) |
C5—C6—C7—C8 | 145.94 (17) | C6—C7—C8—C9 | 177.95 (15) |
N2—C10—C11—C12 | 175.23 (16) | N2—C9—C8—C7 | 175.93 (17) |
C19—C10—C11—C12 | −0.6 (2) | C1—C2—C3—C4 | 0.2 (3) |
C18—C19—C14—C13 | 179.40 (15) | C5—C4—C3—C2 | −0.8 (3) |
C10—C19—C14—C13 | 1.0 (2) |
Experimental details
Crystal data | |
Chemical formula | C19H14N2O2 |
Mr | 302.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.440 (2), 7.4165 (10), 14.598 (2) |
β (°) | 117.347 (2) |
V (Å3) | 1484.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.42 × 0.26 × 0.05 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.964, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8073, 2913, 2014 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.124, 1.03 |
No. of reflections | 2913 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.20 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
As part of our ongoing studies on push-pull Schiff bases, the title compound was synthesized and its crystal structure was determined (Yang et al., 2006).
The molecule is almost planar with a dihedral angle of 3.67 (1)° between the two aromatic rings (Fig. 1). As expected, the bond lengths between the benzene and naphthalene rings in (I) alternates. In the crystal structure the molecules are stacked onto each other with distances of 3.782 and 3.731 Å between the centroids of the rings, indicating for π-π interactions.