organic compounds
In the title compound, C15H12FN3O4, the planes of the nitrophenyl and 4-fluoro-2-hydroxyphenyl fragments form dihedral angles of 25.7 (1) and 10.5 (2)°, respectively, with the C—N—N—C plane of the central hydrazone linkage. In the crystal structure, molecules are linked into layers by intermolecular C—HF and C—HO interactions. Adjacent layers are interlinked by N—HO and C—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023657/ci6446sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023657/ci6446Isup2.hkl |
CCDC reference: 253032
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
1-(4-Fluoro-2-hydroxyphenyl)ethanone 4-nitrobenzoylhydrazone top
Crystal data top
C15H12FN3O4 | F(000) = 656 |
Mr = 317.28 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 936 reflections |
a = 7.4152 (19) Å | θ = 1.7–26.5° |
b = 24.532 (6) Å | µ = 0.12 mm−1 |
c = 8.739 (2) Å | T = 273 K |
β = 113.576 (4)° | Block, brown |
V = 1457.0 (6) Å3 | 0.49 × 0.45 × 0.26 mm |
Z = 4 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3010 independent reflections |
Radiation source: fine-focus sealed tube | 2472 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −30→30 |
Tmin = 0.946, Tmax = 0.971 | l = −10→10 |
15277 measured reflections |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0658P)2 + 0.5534P] where P = (Fo2 + 2Fc2)/3 |
3010 reflections | (Δ/σ)max < 0.001 |
212 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
F1 | 0.8762 (3) | 0.46604 (8) | 1.1637 (3) | 0.1277 (9) | |
O1 | 0.5697 (3) | 0.30336 (7) | 0.9304 (2) | 0.0696 (5) | |
O2 | 0.2124 (3) | 0.20557 (7) | 0.6746 (2) | 0.0719 (5) | |
O3 | −0.2145 (5) | 0.03416 (12) | 0.0102 (4) | 0.1524 (13) | |
O4 | −0.3883 (4) | 0.10036 (14) | −0.1317 (4) | 0.1268 (11) | |
N1 | 0.3251 (3) | 0.30449 (7) | 0.6311 (2) | 0.0498 (4) | |
N2 | 0.2049 (3) | 0.27344 (7) | 0.4973 (2) | 0.0507 (5) | |
H2A | 0.1583 | 0.2859 | 0.3970 | 0.061* | |
N3 | −0.2592 (5) | 0.08227 (14) | −0.0090 (4) | 0.0972 (9) | |
C1 | 0.5029 (4) | 0.44116 (9) | 0.7573 (3) | 0.0586 (6) | |
H1B | 0.4295 | 0.4605 | 0.6608 | 0.070* | |
C2 | 0.6356 (4) | 0.46881 (11) | 0.8914 (4) | 0.0736 (8) | |
H2B | 0.6526 | 0.5063 | 0.8870 | 0.088* | |
C3 | 0.7415 (4) | 0.43971 (13) | 1.0307 (3) | 0.0775 (8) | |
C4 | 0.7196 (4) | 0.38531 (12) | 1.0440 (3) | 0.0710 (7) | |
H4A | 0.7941 | 0.3671 | 1.1425 | 0.085* | |
C5 | 0.5859 (3) | 0.35721 (10) | 0.9100 (3) | 0.0532 (5) | |
C6 | 0.4742 (3) | 0.38506 (8) | 0.7607 (2) | 0.0454 (5) | |
C7 | 0.3353 (3) | 0.35631 (8) | 0.6130 (2) | 0.0450 (5) | |
C8 | 0.2167 (4) | 0.38618 (10) | 0.4561 (3) | 0.0608 (6) | |
H8A | 0.0847 | 0.3722 | 0.4107 | 0.091* | |
H8B | 0.2746 | 0.3812 | 0.3765 | 0.091* | |
H8C | 0.2145 | 0.4243 | 0.4800 | 0.091* | |
C9 | 0.1647 (4) | 0.22256 (9) | 0.5325 (3) | 0.0518 (5) | |
C10 | 0.0525 (3) | 0.18792 (9) | 0.3844 (3) | 0.0512 (5) | |
C11 | 0.0934 (4) | 0.13259 (9) | 0.3988 (3) | 0.0620 (6) | |
H11A | 0.1890 | 0.1188 | 0.4968 | 0.074* | |
C12 | −0.0063 (5) | 0.09819 (10) | 0.2693 (4) | 0.0716 (7) | |
H12A | 0.0215 | 0.0611 | 0.2774 | 0.086* | |
C13 | −0.1476 (4) | 0.11957 (11) | 0.1276 (4) | 0.0680 (7) | |
C14 | −0.1935 (4) | 0.17447 (11) | 0.1084 (3) | 0.0658 (7) | |
H14A | −0.2906 | 0.1879 | 0.0106 | 0.079* | |
C15 | −0.0902 (4) | 0.20864 (9) | 0.2395 (3) | 0.0566 (6) | |
H15A | −0.1166 | 0.2458 | 0.2303 | 0.068* | |
H1 | 0.480 (5) | 0.2897 (13) | 0.824 (4) | 0.099 (10)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1321 (17) | 0.0993 (14) | 0.0930 (14) | −0.0239 (12) | −0.0167 (12) | −0.0322 (11) |
O1 | 0.0835 (12) | 0.0590 (10) | 0.0513 (10) | −0.0008 (9) | 0.0112 (9) | 0.0123 (8) |
O2 | 0.1207 (15) | 0.0541 (9) | 0.0493 (10) | 0.0039 (9) | 0.0427 (10) | 0.0048 (7) |
O3 | 0.194 (3) | 0.089 (2) | 0.160 (3) | −0.048 (2) | 0.055 (2) | −0.0673 (19) |
O4 | 0.1023 (19) | 0.166 (3) | 0.103 (2) | −0.0396 (19) | 0.0317 (16) | −0.0578 (19) |
N1 | 0.0609 (11) | 0.0471 (10) | 0.0397 (9) | −0.0011 (8) | 0.0184 (8) | −0.0027 (7) |
N2 | 0.0673 (11) | 0.0462 (10) | 0.0381 (9) | −0.0044 (8) | 0.0205 (8) | −0.0019 (7) |
N3 | 0.100 (2) | 0.100 (2) | 0.108 (2) | −0.0472 (18) | 0.0587 (19) | −0.0523 (19) |
C1 | 0.0633 (14) | 0.0486 (12) | 0.0591 (13) | 0.0070 (10) | 0.0195 (11) | −0.0041 (10) |
C2 | 0.0802 (18) | 0.0494 (14) | 0.0819 (19) | −0.0028 (12) | 0.0226 (15) | −0.0163 (13) |
C3 | 0.0728 (17) | 0.0771 (19) | 0.0633 (16) | −0.0052 (14) | 0.0070 (14) | −0.0214 (14) |
C4 | 0.0712 (16) | 0.0750 (18) | 0.0499 (14) | 0.0041 (13) | 0.0065 (12) | −0.0025 (12) |
C5 | 0.0543 (12) | 0.0567 (13) | 0.0462 (12) | 0.0025 (10) | 0.0176 (10) | −0.0018 (10) |
C6 | 0.0458 (11) | 0.0477 (11) | 0.0433 (11) | 0.0052 (9) | 0.0184 (9) | −0.0025 (9) |
C7 | 0.0492 (11) | 0.0465 (11) | 0.0412 (11) | 0.0056 (9) | 0.0200 (9) | −0.0003 (8) |
C8 | 0.0701 (15) | 0.0547 (13) | 0.0464 (12) | 0.0040 (11) | 0.0115 (11) | 0.0000 (10) |
C9 | 0.0706 (14) | 0.0448 (11) | 0.0492 (12) | 0.0023 (10) | 0.0336 (11) | 0.0004 (9) |
C10 | 0.0651 (14) | 0.0456 (11) | 0.0553 (13) | −0.0074 (10) | 0.0372 (11) | −0.0035 (9) |
C11 | 0.0801 (16) | 0.0462 (12) | 0.0707 (16) | −0.0045 (11) | 0.0419 (13) | −0.0023 (11) |
C12 | 0.092 (2) | 0.0461 (13) | 0.095 (2) | −0.0113 (13) | 0.0568 (18) | −0.0133 (13) |
C13 | 0.0739 (16) | 0.0663 (16) | 0.0806 (18) | −0.0271 (13) | 0.0485 (15) | −0.0272 (14) |
C14 | 0.0605 (15) | 0.0767 (17) | 0.0652 (15) | −0.0153 (12) | 0.0304 (12) | −0.0072 (13) |
C15 | 0.0648 (14) | 0.0489 (12) | 0.0629 (14) | −0.0074 (10) | 0.0328 (12) | −0.0024 (10) |
Geometric parameters (Å, º) top
F1—C3 | 1.355 (3) | C4—H4A | 0.93 |
O1—C5 | 1.345 (3) | C5—C6 | 1.411 (3) |
O1—H1 | 0.96 (3) | C6—C7 | 1.470 (3) |
O2—C9 | 1.220 (3) | C7—C8 | 1.492 (3) |
O3—N3 | 1.219 (4) | C8—H8A | 0.96 |
O4—N3 | 1.201 (4) | C8—H8B | 0.96 |
N1—C7 | 1.287 (3) | C8—H8C | 0.96 |
N1—N2 | 1.381 (2) | C9—C10 | 1.493 (3) |
N2—C9 | 1.347 (3) | C10—C15 | 1.382 (3) |
N2—H2A | 0.86 | C10—C11 | 1.386 (3) |
N3—C13 | 1.469 (4) | C11—C12 | 1.368 (4) |
C1—C2 | 1.371 (3) | C11—H11A | 0.93 |
C1—C6 | 1.395 (3) | C12—C13 | 1.367 (4) |
C1—H1B | 0.93 | C12—H12A | 0.93 |
C2—C3 | 1.358 (4) | C13—C14 | 1.383 (4) |
C2—H2B | 0.93 | C14—C15 | 1.378 (3) |
C3—C4 | 1.355 (4) | C14—H14A | 0.93 |
C4—C5 | 1.379 (3) | C15—H15A | 0.93 |
C5—O1—H1 | 106.1 (19) | C6—C7—C8 | 121.32 (19) |
C7—N1—N2 | 119.37 (17) | C7—C8—H8A | 109.5 |
C9—N2—N1 | 116.39 (17) | C7—C8—H8B | 109.5 |
C9—N2—H2A | 121.8 | H8A—C8—H8B | 109.5 |
N1—N2—H2A | 121.8 | C7—C8—H8C | 109.5 |
O4—N3—O3 | 123.8 (3) | H8A—C8—H8C | 109.5 |
O4—N3—C13 | 119.0 (3) | H8B—C8—H8C | 109.5 |
O3—N3—C13 | 117.2 (4) | O2—C9—N2 | 123.3 (2) |
C2—C1—C6 | 122.3 (2) | O2—C9—C10 | 121.4 (2) |
C2—C1—H1B | 118.9 | N2—C9—C10 | 115.29 (18) |
C6—C1—H1B | 118.9 | C15—C10—C11 | 120.2 (2) |
C3—C2—C1 | 117.8 (2) | C15—C10—C9 | 122.8 (2) |
C3—C2—H2B | 121.1 | C11—C10—C9 | 117.0 (2) |
C1—C2—H2B | 121.1 | C12—C11—C10 | 120.2 (3) |
C4—C3—F1 | 117.9 (3) | C12—C11—H11A | 119.9 |
C4—C3—C2 | 123.3 (2) | C10—C11—H11A | 119.9 |
F1—C3—C2 | 118.8 (3) | C13—C12—C11 | 118.5 (2) |
C3—C4—C5 | 119.3 (2) | C13—C12—H12A | 120.7 |
C3—C4—H4A | 120.3 | C11—C12—H12A | 120.7 |
C5—C4—H4A | 120.3 | C12—C13—C14 | 123.1 (2) |
O1—C5—C4 | 116.8 (2) | C12—C13—N3 | 118.4 (3) |
O1—C5—C6 | 123.2 (2) | C14—C13—N3 | 118.5 (3) |
C4—C5—C6 | 120.0 (2) | C15—C14—C13 | 117.6 (3) |
C1—C6—C5 | 117.3 (2) | C15—C14—H14A | 121.2 |
C1—C6—C7 | 120.94 (19) | C13—C14—H14A | 121.2 |
C5—C6—C7 | 121.71 (19) | C14—C15—C10 | 120.4 (2) |
N1—C7—C6 | 114.91 (18) | C14—C15—H15A | 119.8 |
N1—C7—C8 | 123.78 (19) | C10—C15—H15A | 119.8 |
C7—N1—N2—C9 | −165.1 (2) | N1—N2—C9—O2 | 7.4 (3) |
C6—C1—C2—C3 | 0.2 (4) | N1—N2—C9—C10 | −173.80 (18) |
C1—C2—C3—C4 | −1.1 (5) | O2—C9—C10—C15 | 143.9 (2) |
C1—C2—C3—F1 | 178.8 (3) | N2—C9—C10—C15 | −34.9 (3) |
F1—C3—C4—C5 | −179.0 (3) | O2—C9—C10—C11 | −34.4 (3) |
C2—C3—C4—C5 | 0.9 (5) | N2—C9—C10—C11 | 146.8 (2) |
C3—C4—C5—O1 | −179.7 (3) | C15—C10—C11—C12 | 0.4 (3) |
C3—C4—C5—C6 | 0.3 (4) | C9—C10—C11—C12 | 178.8 (2) |
C2—C1—C6—C5 | 1.0 (3) | C10—C11—C12—C13 | −0.8 (4) |
C2—C1—C6—C7 | −178.0 (2) | C11—C12—C13—C14 | 0.6 (4) |
O1—C5—C6—C1 | 178.9 (2) | C11—C12—C13—N3 | −177.9 (2) |
C4—C5—C6—C1 | −1.2 (3) | O4—N3—C13—C12 | 177.4 (3) |
O1—C5—C6—C7 | −2.2 (3) | O3—N3—C13—C12 | −2.2 (4) |
C4—C5—C6—C7 | 177.8 (2) | O4—N3—C13—C14 | −1.1 (4) |
N2—N1—C7—C6 | −177.31 (17) | O3—N3—C13—C14 | 179.2 (3) |
N2—N1—C7—C8 | 2.9 (3) | C12—C13—C14—C15 | 0.1 (4) |
C1—C6—C7—N1 | 178.7 (2) | N3—C13—C14—C15 | 178.6 (2) |
C5—C6—C7—N1 | −0.3 (3) | C13—C14—C15—C10 | −0.5 (3) |
C1—C6—C7—C8 | −1.5 (3) | C11—C10—C15—C14 | 0.3 (3) |
C5—C6—C7—C8 | 179.5 (2) | C9—C10—C15—C14 | −178.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.96 (3) | 1.66 (3) | 2.517 (2) | 147 (3) |
N2—H2A···O2i | 0.86 | 2.15 | 2.889 (3) | 144 |
C1—H1B···O3ii | 0.93 | 2.48 | 3.353 (4) | 157 |
C8—H8B···O4iii | 0.96 | 2.57 | 3.328 (5) | 136 |
C12—H12A···F1iv | 0.93 | 2.44 | 3.366 (3) | 173 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+3/2. |