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The title compound, C18H13NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007290/ob1032sup1.cif
Contains datablocks I, SOSA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007290/ob1032Isup2.hkl
Contains datablock I

CCDC reference: 150841

Computing details top

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.

(I) top
Crystal data top
C18H13NO3F(000) = 608
Mr = 291.29Dx = 1.423 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.665 (2) ÅCell parameters from 28 reflections
b = 7.4718 (11) Åθ = 9.1–16.9°
c = 16.2794 (15) ŵ = 0.10 mm1
β = 106.666 (14)°T = 293 K
V = 1359.3 (3) Å3Plate, pale orange
Z = 40.55 × 0.24 × 0.04 mm
Data collection top
Philips PW1100 upgraded by Stoe
diffractometer
Rint = 0.014
Radiation source: fine-focus sealed tubeθmax = 26.9°, θmin = 3.0°
Graphite monochromatorh = 1414
ω scank = 09
2968 measured reflectionsl = 020
2866 independent reflections3 standard reflections every 90 min
1374 reflections with I > 2σ(I) intensity decay: 6.8%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: d
wR(F2) = 0.117All H-atom parameters refined
S = 0.94Calculated w = 1/[σ2(Fo2) + (0.0551P)2]
where P = (Fo2 + 2Fc2)/3
2866 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.17 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.79030 (14)0.0436 (2)0.47774 (9)0.0548 (5)
O20.24254 (14)0.4589 (3)0.18395 (10)0.0564 (5)
O30.42353 (15)0.3607 (3)0.18791 (9)0.0614 (5)
N10.59994 (16)0.1765 (3)0.49675 (11)0.0388 (5)
C10.75524 (17)0.0632 (3)0.61407 (12)0.0337 (5)
C20.8261 (2)0.0117 (3)0.55899 (13)0.0396 (5)
C30.9375 (2)0.0785 (3)0.59532 (15)0.0463 (6)
C40.9766 (2)0.1127 (3)0.67963 (15)0.0446 (6)
C50.9109 (2)0.0626 (3)0.73771 (13)0.0387 (5)
C60.9548 (2)0.1027 (3)0.82586 (15)0.0491 (6)
C70.8918 (2)0.0541 (4)0.88105 (16)0.0559 (7)
C80.7835 (2)0.0347 (4)0.85081 (15)0.0547 (7)
C90.7373 (2)0.0737 (3)0.76472 (13)0.0453 (6)
C100.8001 (2)0.0263 (3)0.70633 (12)0.0349 (5)
C110.6442 (2)0.1436 (3)0.57941 (13)0.0349 (5)
C120.4908 (2)0.2591 (3)0.45271 (12)0.0338 (5)
C130.4710 (2)0.2867 (3)0.36516 (12)0.0349 (5)
C140.3664 (2)0.3670 (3)0.31713 (12)0.0340 (5)
C150.2809 (2)0.4187 (3)0.35610 (13)0.0389 (6)
C160.3012 (2)0.3900 (3)0.44310 (14)0.0415 (6)
C170.4052 (2)0.3117 (3)0.49221 (14)0.0374 (5)
C180.3484 (2)0.3942 (3)0.22361 (13)0.0390 (5)
H30.986 (2)0.108 (3)0.5589 (15)0.054 (7)*
H41.050 (2)0.176 (3)0.7008 (14)0.047 (6)*
H61.034 (2)0.171 (4)0.8489 (15)0.062 (7)*
H70.923 (2)0.087 (3)0.9400 (17)0.062 (8)*
H80.732 (2)0.069 (3)0.8882 (16)0.067 (8)*
H90.658 (2)0.132 (3)0.7449 (14)0.051 (7)*
H110.597 (2)0.175 (3)0.6147 (14)0.047 (6)*
H130.529 (2)0.251 (3)0.3374 (13)0.040 (6)*
H150.212 (2)0.468 (3)0.3224 (14)0.045 (6)*
H160.241 (2)0.424 (3)0.4698 (15)0.062 (7)*
H170.4195 (17)0.295 (3)0.5528 (14)0.041 (6)*
H1N0.651 (2)0.141 (3)0.4676 (14)0.050 (7)*
H2O0.235 (3)0.482 (4)0.127 (2)0.096 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0504 (9)0.0861 (14)0.0278 (8)0.0044 (9)0.0108 (7)0.0027 (8)
O20.0507 (10)0.0880 (15)0.0287 (9)0.0164 (10)0.0086 (8)0.0137 (9)
O30.0488 (9)0.1066 (15)0.0312 (8)0.0050 (10)0.0155 (8)0.0041 (9)
N10.0368 (10)0.0498 (13)0.0286 (9)0.0004 (9)0.0072 (8)0.0000 (9)
C10.0355 (11)0.0357 (12)0.0271 (10)0.0064 (10)0.0043 (9)0.0022 (9)
C20.0412 (12)0.0490 (14)0.0285 (11)0.0076 (11)0.0099 (10)0.0069 (10)
C30.0396 (13)0.0564 (17)0.0449 (14)0.0009 (12)0.0156 (11)0.0043 (12)
C40.0340 (13)0.0498 (15)0.0461 (14)0.0015 (11)0.0051 (11)0.0002 (12)
C50.0388 (12)0.0367 (13)0.0363 (11)0.0058 (11)0.0041 (10)0.0009 (10)
C60.0467 (14)0.0531 (16)0.0409 (13)0.0007 (13)0.0021 (11)0.0084 (12)
C70.0631 (17)0.068 (2)0.0304 (12)0.0027 (15)0.0030 (12)0.0097 (12)
C80.0598 (16)0.072 (2)0.0323 (12)0.0044 (15)0.0132 (12)0.0040 (12)
C90.0470 (14)0.0561 (16)0.0316 (12)0.0048 (12)0.0093 (10)0.0014 (11)
C100.0364 (11)0.0363 (13)0.0295 (10)0.0047 (10)0.0053 (9)0.0003 (9)
C110.0375 (12)0.0400 (13)0.0252 (10)0.0047 (10)0.0062 (9)0.0012 (9)
C120.0341 (11)0.0347 (13)0.0286 (10)0.0057 (10)0.0026 (9)0.0011 (9)
C130.0349 (12)0.0432 (14)0.0267 (10)0.0041 (11)0.0088 (9)0.0028 (10)
C140.0371 (11)0.0351 (12)0.0281 (10)0.0050 (10)0.0066 (9)0.0005 (9)
C150.0376 (12)0.0467 (15)0.0311 (11)0.0036 (11)0.0076 (10)0.0011 (10)
C160.0433 (13)0.0479 (15)0.0363 (12)0.0026 (11)0.0164 (11)0.0025 (11)
C170.0439 (13)0.0433 (14)0.0255 (11)0.0038 (11)0.0108 (10)0.0018 (10)
C180.0391 (12)0.0495 (15)0.0277 (11)0.0047 (11)0.0086 (10)0.0018 (10)
Geometric parameters (Å, º) top
O1—C21.290 (2)C13—C141.383 (3)
O2—C181.311 (3)C14—C151.382 (3)
O3—C181.208 (3)C14—C181.490 (3)
N1—C111.319 (3)C15—C161.384 (3)
N1—C121.411 (3)C16—C171.377 (3)
C1—C111.392 (3)O2—H2O0.92 (3)
C1—C21.435 (3)N1—H1N0.90 (2)
C1—C101.468 (3)C3—H30.96 (2)
C2—C31.433 (3)C4—H40.95 (2)
C3—C41.341 (3)C6—H61.03 (3)
C4—C51.427 (3)C7—H70.96 (3)
C5—C61.411 (3)C8—H81.00 (2)
C5—C101.413 (3)C9—H90.99 (2)
C6—C71.363 (4)C11—H110.93 (2)
C7—C81.386 (4)C13—H130.96 (2)
C8—C91.381 (3)C15—H150.91 (2)
C9—C101.402 (3)C16—H160.96 (2)
C12—C171.390 (3)C17—H170.96 (2)
C12—C131.392 (3)
C11—N1—C12129.2 (2)C16—C17—C12118.8 (2)
C11—C1—C2119.9 (2)O3—C18—O2123.4 (2)
C11—C1—C10120.8 (2)O3—C18—C14123.7 (2)
C2—C1—C10119.3 (2)O2—C18—C14113.0 (2)
O1—C2—C3119.9 (2)C18—O2—H2O112 (2)
O1—C2—C1121.1 (2)C12—N1—H1N119.8 (14)
C3—C2—C1119.0 (2)C11—N1—H1N111.0 (14)
C4—C3—C2120.9 (2)C2—C3—H3118.7 (14)
C3—C4—C5122.6 (2)C4—C3—H3120.2 (14)
C6—C5—C10119.7 (2)C3—C4—H4118.2 (14)
C6—C5—C4120.7 (2)C5—C4—H4119.2 (14)
C10—C5—C4119.6 (2)C5—C6—H6120.2 (13)
C7—C6—C5120.4 (2)C7—C6—H6119.3 (13)
C6—C7—C8120.2 (2)C6—C7—H7118.1 (15)
C9—C8—C7120.8 (3)C8—C7—H7121.7 (15)
C8—C9—C10120.5 (2)C7—C8—H8123.4 (14)
C9—C10—C5118.4 (2)C9—C8—H8115.8 (14)
C9—C10—C1123.0 (2)C8—C9—H9118.7 (13)
C5—C10—C1118.6 (2)C10—C9—H9120.8 (13)
N1—C11—C1122.7 (2)N1—C11—H11117.0 (14)
C17—C12—C13120.1 (2)C1—C11—H11120.3 (14)
C17—C12—N1123.5 (2)C12—C13—H13120.7 (13)
C13—C12—N1116.5 (2)C14—C13—H13119.0 (13)
C14—C13—C12120.2 (2)C14—C15—H15117.7 (14)
C15—C14—C13119.8 (2)C16—C15—H15122.8 (14)
C15—C14—C18121.5 (2)C15—C16—H16119.3 (14)
C13—C14—C18118.7 (2)C17—C16—H16119.1 (14)
C14—C15—C16119.5 (2)C12—C17—H17120.2 (13)
C17—C16—C15121.6 (2)C16—C17—H17121.0 (13)
C11—C1—C2—O12.2 (3)C11—C1—C10—C5177.3 (2)
C10—C1—C2—O1179.3 (2)C2—C1—C10—C51.3 (3)
C11—C1—C2—C3177.1 (2)C12—N1—C11—C1178.8 (2)
C10—C1—C2—C31.5 (3)C2—C1—C11—N10.4 (3)
O1—C2—C3—C4179.9 (2)C10—C1—C11—N1178.9 (2)
C1—C2—C3—C40.9 (3)C11—N1—C12—C174.2 (4)
C2—C3—C4—C50.1 (4)C11—N1—C12—C13175.9 (2)
C3—C4—C5—C6179.4 (2)C17—C12—C13—C140.2 (3)
C3—C4—C5—C100.1 (4)N1—C12—C13—C14179.9 (2)
C10—C5—C6—C70.9 (3)C12—C13—C14—C150.6 (3)
C4—C5—C6—C7179.8 (2)C12—C13—C14—C18180.0 (2)
C5—C6—C7—C80.3 (4)C13—C14—C15—C160.3 (3)
C6—C7—C8—C90.6 (4)C18—C14—C15—C16179.7 (2)
C7—C8—C9—C100.9 (4)C14—C15—C16—C170.3 (3)
C8—C9—C10—C50.3 (3)C15—C16—C17—C120.6 (3)
C8—C9—C10—C1179.6 (2)C13—C12—C17—C160.4 (3)
C6—C5—C10—C90.6 (3)N1—C12—C17—C16179.5 (2)
C4—C5—C10—C9179.9 (2)C15—C14—C18—O3175.5 (2)
C6—C5—C10—C1178.8 (2)C13—C14—C18—O35.1 (3)
C4—C5—C10—C10.5 (3)C15—C14—C18—O24.2 (3)
C11—C1—C10—C92.1 (3)C13—C14—C18—O2175.2 (2)
C2—C1—C10—C9179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.90 (2)1.74 (2)2.531 (3)144.3 (2)
O2—H2O···O1i0.92 (3)1.71 (3)2.626 (2)173.7 (3)
C17—H17···O3ii0.96 (2)2.48 (2)3.386 (3)158.2 (2)
C15—H15···O20.91 (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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