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The title compound, C
18H
13NO
3, exists as a ketoamino tautomer implying a fairly short N—H
O intramolecular hydrogen bond between the 2-naphthalenone and amino moieties [N
O 2.531 (3) Å] which is enhanced by the π-electron delocalization effect. The naphthaldimine and 3-carboxyphenyl fragments are inclined at an angle of 4.41 (7)°, so the molecule is almost planar. The molecules are connected by intermolecular O—H
O hydrogen bonds between the carboxy and keto O atoms, forming infinite chains around the twofold screw axes parallel to
b.
Supporting information
CCDC reference: 150841
Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.
Crystal data top
C18H13NO3 | F(000) = 608 |
Mr = 291.29 | Dx = 1.423 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.665 (2) Å | Cell parameters from 28 reflections |
b = 7.4718 (11) Å | θ = 9.1–16.9° |
c = 16.2794 (15) Å | µ = 0.10 mm−1 |
β = 106.666 (14)° | T = 293 K |
V = 1359.3 (3) Å3 | Plate, pale orange |
Z = 4 | 0.55 × 0.24 × 0.04 mm |
Data collection top
Philips PW1100 upgraded by Stoe diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 26.9°, θmin = 3.0° |
Graphite monochromator | h = −14→14 |
ω scan | k = 0→9 |
2968 measured reflections | l = 0→20 |
2866 independent reflections | 3 standard reflections every 90 min |
1374 reflections with I > 2σ(I) | intensity decay: 6.8% |
Refinement top
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)] = 0.046 | Hydrogen site location: d |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 0.94 | Calculated w = 1/[σ2(Fo2) + (0.0551P)2] where P = (Fo2 + 2Fc2)/3 |
2866 reflections | (Δ/σ)max < 0.001 |
251 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79030 (14) | 0.0436 (2) | 0.47774 (9) | 0.0548 (5) | |
O2 | 0.24254 (14) | 0.4589 (3) | 0.18395 (10) | 0.0564 (5) | |
O3 | 0.42353 (15) | 0.3607 (3) | 0.18791 (9) | 0.0614 (5) | |
N1 | 0.59994 (16) | 0.1765 (3) | 0.49675 (11) | 0.0388 (5) | |
C1 | 0.75524 (17) | 0.0632 (3) | 0.61407 (12) | 0.0337 (5) | |
C2 | 0.8261 (2) | 0.0117 (3) | 0.55899 (13) | 0.0396 (5) | |
C3 | 0.9375 (2) | −0.0785 (3) | 0.59532 (15) | 0.0463 (6) | |
C4 | 0.9766 (2) | −0.1127 (3) | 0.67963 (15) | 0.0446 (6) | |
C5 | 0.9109 (2) | −0.0626 (3) | 0.73771 (13) | 0.0387 (5) | |
C6 | 0.9548 (2) | −0.1027 (3) | 0.82586 (15) | 0.0491 (6) | |
C7 | 0.8918 (2) | −0.0541 (4) | 0.88105 (16) | 0.0559 (7) | |
C8 | 0.7835 (2) | 0.0347 (4) | 0.85081 (15) | 0.0547 (7) | |
C9 | 0.7373 (2) | 0.0737 (3) | 0.76472 (13) | 0.0453 (6) | |
C10 | 0.8001 (2) | 0.0263 (3) | 0.70633 (12) | 0.0349 (5) | |
C11 | 0.6442 (2) | 0.1436 (3) | 0.57941 (13) | 0.0349 (5) | |
C12 | 0.4908 (2) | 0.2591 (3) | 0.45271 (12) | 0.0338 (5) | |
C13 | 0.4710 (2) | 0.2867 (3) | 0.36516 (12) | 0.0349 (5) | |
C14 | 0.3664 (2) | 0.3670 (3) | 0.31713 (12) | 0.0340 (5) | |
C15 | 0.2809 (2) | 0.4187 (3) | 0.35610 (13) | 0.0389 (6) | |
C16 | 0.3012 (2) | 0.3900 (3) | 0.44310 (14) | 0.0415 (6) | |
C17 | 0.4052 (2) | 0.3117 (3) | 0.49221 (14) | 0.0374 (5) | |
C18 | 0.3484 (2) | 0.3942 (3) | 0.22361 (13) | 0.0390 (5) | |
H3 | 0.986 (2) | −0.108 (3) | 0.5589 (15) | 0.054 (7)* | |
H4 | 1.050 (2) | −0.176 (3) | 0.7008 (14) | 0.047 (6)* | |
H6 | 1.034 (2) | −0.171 (4) | 0.8489 (15) | 0.062 (7)* | |
H7 | 0.923 (2) | −0.087 (3) | 0.9400 (17) | 0.062 (8)* | |
H8 | 0.732 (2) | 0.069 (3) | 0.8882 (16) | 0.067 (8)* | |
H9 | 0.658 (2) | 0.132 (3) | 0.7449 (14) | 0.051 (7)* | |
H11 | 0.597 (2) | 0.175 (3) | 0.6147 (14) | 0.047 (6)* | |
H13 | 0.529 (2) | 0.251 (3) | 0.3374 (13) | 0.040 (6)* | |
H15 | 0.212 (2) | 0.468 (3) | 0.3224 (14) | 0.045 (6)* | |
H16 | 0.241 (2) | 0.424 (3) | 0.4698 (15) | 0.062 (7)* | |
H17 | 0.4195 (17) | 0.295 (3) | 0.5528 (14) | 0.041 (6)* | |
H1N | 0.651 (2) | 0.141 (3) | 0.4676 (14) | 0.050 (7)* | |
H2O | 0.235 (3) | 0.482 (4) | 0.127 (2) | 0.096 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0504 (9) | 0.0861 (14) | 0.0278 (8) | 0.0044 (9) | 0.0108 (7) | −0.0027 (8) |
O2 | 0.0507 (10) | 0.0880 (15) | 0.0287 (9) | 0.0164 (10) | 0.0086 (8) | 0.0137 (9) |
O3 | 0.0488 (9) | 0.1066 (15) | 0.0312 (8) | 0.0050 (10) | 0.0155 (8) | 0.0041 (9) |
N1 | 0.0368 (10) | 0.0498 (13) | 0.0286 (9) | −0.0004 (9) | 0.0072 (8) | 0.0000 (9) |
C1 | 0.0355 (11) | 0.0357 (12) | 0.0271 (10) | −0.0064 (10) | 0.0043 (9) | −0.0022 (9) |
C2 | 0.0412 (12) | 0.0490 (14) | 0.0285 (11) | −0.0076 (11) | 0.0099 (10) | −0.0069 (10) |
C3 | 0.0396 (13) | 0.0564 (17) | 0.0449 (14) | −0.0009 (12) | 0.0156 (11) | −0.0043 (12) |
C4 | 0.0340 (13) | 0.0498 (15) | 0.0461 (14) | 0.0015 (11) | 0.0051 (11) | 0.0002 (12) |
C5 | 0.0388 (12) | 0.0367 (13) | 0.0363 (11) | −0.0058 (11) | 0.0041 (10) | −0.0009 (10) |
C6 | 0.0467 (14) | 0.0531 (16) | 0.0409 (13) | 0.0007 (13) | 0.0021 (11) | 0.0084 (12) |
C7 | 0.0631 (17) | 0.068 (2) | 0.0304 (12) | 0.0027 (15) | 0.0030 (12) | 0.0097 (12) |
C8 | 0.0598 (16) | 0.072 (2) | 0.0323 (12) | 0.0044 (15) | 0.0132 (12) | 0.0040 (12) |
C9 | 0.0470 (14) | 0.0561 (16) | 0.0316 (12) | 0.0048 (12) | 0.0093 (10) | −0.0014 (11) |
C10 | 0.0364 (11) | 0.0363 (13) | 0.0295 (10) | −0.0047 (10) | 0.0053 (9) | −0.0003 (9) |
C11 | 0.0375 (12) | 0.0400 (13) | 0.0252 (10) | −0.0047 (10) | 0.0062 (9) | −0.0012 (9) |
C12 | 0.0341 (11) | 0.0347 (13) | 0.0286 (10) | −0.0057 (10) | 0.0026 (9) | −0.0011 (9) |
C13 | 0.0349 (12) | 0.0432 (14) | 0.0267 (10) | −0.0041 (11) | 0.0088 (9) | −0.0028 (10) |
C14 | 0.0371 (11) | 0.0351 (12) | 0.0281 (10) | −0.0050 (10) | 0.0066 (9) | −0.0005 (9) |
C15 | 0.0376 (12) | 0.0467 (15) | 0.0311 (11) | 0.0036 (11) | 0.0076 (10) | 0.0011 (10) |
C16 | 0.0433 (13) | 0.0479 (15) | 0.0363 (12) | 0.0026 (11) | 0.0164 (11) | −0.0025 (11) |
C17 | 0.0439 (13) | 0.0433 (14) | 0.0255 (11) | −0.0038 (11) | 0.0108 (10) | −0.0018 (10) |
C18 | 0.0391 (12) | 0.0495 (15) | 0.0277 (11) | −0.0047 (11) | 0.0086 (10) | −0.0018 (10) |
Geometric parameters (Å, º) top
O1—C2 | 1.290 (2) | C13—C14 | 1.383 (3) |
O2—C18 | 1.311 (3) | C14—C15 | 1.382 (3) |
O3—C18 | 1.208 (3) | C14—C18 | 1.490 (3) |
N1—C11 | 1.319 (3) | C15—C16 | 1.384 (3) |
N1—C12 | 1.411 (3) | C16—C17 | 1.377 (3) |
C1—C11 | 1.392 (3) | O2—H2O | 0.92 (3) |
C1—C2 | 1.435 (3) | N1—H1N | 0.90 (2) |
C1—C10 | 1.468 (3) | C3—H3 | 0.96 (2) |
C2—C3 | 1.433 (3) | C4—H4 | 0.95 (2) |
C3—C4 | 1.341 (3) | C6—H6 | 1.03 (3) |
C4—C5 | 1.427 (3) | C7—H7 | 0.96 (3) |
C5—C6 | 1.411 (3) | C8—H8 | 1.00 (2) |
C5—C10 | 1.413 (3) | C9—H9 | 0.99 (2) |
C6—C7 | 1.363 (4) | C11—H11 | 0.93 (2) |
C7—C8 | 1.386 (4) | C13—H13 | 0.96 (2) |
C8—C9 | 1.381 (3) | C15—H15 | 0.91 (2) |
C9—C10 | 1.402 (3) | C16—H16 | 0.96 (2) |
C12—C17 | 1.390 (3) | C17—H17 | 0.96 (2) |
C12—C13 | 1.392 (3) | | |
| | | |
C11—N1—C12 | 129.2 (2) | C16—C17—C12 | 118.8 (2) |
C11—C1—C2 | 119.9 (2) | O3—C18—O2 | 123.4 (2) |
C11—C1—C10 | 120.8 (2) | O3—C18—C14 | 123.7 (2) |
C2—C1—C10 | 119.3 (2) | O2—C18—C14 | 113.0 (2) |
O1—C2—C3 | 119.9 (2) | C18—O2—H2O | 112 (2) |
O1—C2—C1 | 121.1 (2) | C12—N1—H1N | 119.8 (14) |
C3—C2—C1 | 119.0 (2) | C11—N1—H1N | 111.0 (14) |
C4—C3—C2 | 120.9 (2) | C2—C3—H3 | 118.7 (14) |
C3—C4—C5 | 122.6 (2) | C4—C3—H3 | 120.2 (14) |
C6—C5—C10 | 119.7 (2) | C3—C4—H4 | 118.2 (14) |
C6—C5—C4 | 120.7 (2) | C5—C4—H4 | 119.2 (14) |
C10—C5—C4 | 119.6 (2) | C5—C6—H6 | 120.2 (13) |
C7—C6—C5 | 120.4 (2) | C7—C6—H6 | 119.3 (13) |
C6—C7—C8 | 120.2 (2) | C6—C7—H7 | 118.1 (15) |
C9—C8—C7 | 120.8 (3) | C8—C7—H7 | 121.7 (15) |
C8—C9—C10 | 120.5 (2) | C7—C8—H8 | 123.4 (14) |
C9—C10—C5 | 118.4 (2) | C9—C8—H8 | 115.8 (14) |
C9—C10—C1 | 123.0 (2) | C8—C9—H9 | 118.7 (13) |
C5—C10—C1 | 118.6 (2) | C10—C9—H9 | 120.8 (13) |
N1—C11—C1 | 122.7 (2) | N1—C11—H11 | 117.0 (14) |
C17—C12—C13 | 120.1 (2) | C1—C11—H11 | 120.3 (14) |
C17—C12—N1 | 123.5 (2) | C12—C13—H13 | 120.7 (13) |
C13—C12—N1 | 116.5 (2) | C14—C13—H13 | 119.0 (13) |
C14—C13—C12 | 120.2 (2) | C14—C15—H15 | 117.7 (14) |
C15—C14—C13 | 119.8 (2) | C16—C15—H15 | 122.8 (14) |
C15—C14—C18 | 121.5 (2) | C15—C16—H16 | 119.3 (14) |
C13—C14—C18 | 118.7 (2) | C17—C16—H16 | 119.1 (14) |
C14—C15—C16 | 119.5 (2) | C12—C17—H17 | 120.2 (13) |
C17—C16—C15 | 121.6 (2) | C16—C17—H17 | 121.0 (13) |
| | | |
C11—C1—C2—O1 | 2.2 (3) | C11—C1—C10—C5 | 177.3 (2) |
C10—C1—C2—O1 | −179.3 (2) | C2—C1—C10—C5 | −1.3 (3) |
C11—C1—C2—C3 | −177.1 (2) | C12—N1—C11—C1 | −178.8 (2) |
C10—C1—C2—C3 | 1.5 (3) | C2—C1—C11—N1 | −0.4 (3) |
O1—C2—C3—C4 | 179.9 (2) | C10—C1—C11—N1 | −178.9 (2) |
C1—C2—C3—C4 | −0.9 (3) | C11—N1—C12—C17 | −4.2 (4) |
C2—C3—C4—C5 | 0.1 (4) | C11—N1—C12—C13 | 175.9 (2) |
C3—C4—C5—C6 | 179.4 (2) | C17—C12—C13—C14 | 0.2 (3) |
C3—C4—C5—C10 | 0.1 (4) | N1—C12—C13—C14 | −179.9 (2) |
C10—C5—C6—C7 | −0.9 (3) | C12—C13—C14—C15 | −0.6 (3) |
C4—C5—C6—C7 | 179.8 (2) | C12—C13—C14—C18 | −180.0 (2) |
C5—C6—C7—C8 | 0.3 (4) | C13—C14—C15—C16 | 0.3 (3) |
C6—C7—C8—C9 | 0.6 (4) | C18—C14—C15—C16 | 179.7 (2) |
C7—C8—C9—C10 | −0.9 (4) | C14—C15—C16—C17 | 0.3 (3) |
C8—C9—C10—C5 | 0.3 (3) | C15—C16—C17—C12 | −0.6 (3) |
C8—C9—C10—C1 | 179.6 (2) | C13—C12—C17—C16 | 0.4 (3) |
C6—C5—C10—C9 | 0.6 (3) | N1—C12—C17—C16 | −179.5 (2) |
C4—C5—C10—C9 | 179.9 (2) | C15—C14—C18—O3 | 175.5 (2) |
C6—C5—C10—C1 | −178.8 (2) | C13—C14—C18—O3 | −5.1 (3) |
C4—C5—C10—C1 | 0.5 (3) | C15—C14—C18—O2 | −4.2 (3) |
C11—C1—C10—C9 | −2.1 (3) | C13—C14—C18—O2 | 175.2 (2) |
C2—C1—C10—C9 | 179.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.90 (2) | 1.74 (2) | 2.531 (3) | 144.3 (2) |
O2—H2O···O1i | 0.92 (3) | 1.71 (3) | 2.626 (2) | 173.7 (3) |
C17—H17···O3ii | 0.96 (2) | 2.48 (2) | 3.386 (3) | 158.2 (2) |
C15—H15···O2 | 0.91 (2) | 2.38 (2) | 2.725 (3) | 102.0 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
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