The title compound, C
18H
18N
2O
2, was prepared by the reaction of (
E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one with hydrazine hydrate in acetic acid. The crystal packing is stabilized by weak C—H
O hydrogen bonds.
Supporting information
CCDC reference: 628406
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C)= 0.003 Å
- R factor = 0.049
- wR factor = 0.154
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-[3-(4-methoxyphenyl)-5-phenyl-4,5-dihydro-1
H-pyrazol-1-yl]ethanone
top
Crystal data top
C18H18N2O2 | F(000) = 624 |
Mr = 294.34 | Dx = 1.255 Mg m−3 |
Monoclinic, P21/c | Melting point: 138 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.960 (2) Å | Cell parameters from 25 reflections |
b = 12.089 (2) Å | θ = 4–14° |
c = 11.044 (2) Å | µ = 0.08 mm−1 |
β = 102.68 (3)° | T = 293 K |
V = 1557.8 (5) Å3 | Block, colorless |
Z = 4 | 0.28 × 0.22 × 0.17 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 1.8° |
Graphite monochromator | h = −14→14 |
ω scans | k = −14→0 |
3537 measured reflections | l = 0→13 |
3359 independent reflections | 3 standard reflections every 200 reflections |
2066 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.079P)2 + 0.2729P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3359 reflections | Δρmax = 0.23 e Å−3 |
200 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (2) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.98479 (14) | 0.27624 (14) | 0.26720 (15) | 0.0697 (5) | |
O2 | 0.65020 (14) | 0.90848 (13) | −0.25511 (15) | 0.0680 (5) | |
N1 | 0.88623 (12) | 0.51051 (13) | 0.08538 (14) | 0.0435 (4) | |
N2 | 0.91664 (13) | 0.40145 (13) | 0.12012 (14) | 0.0445 (4) | |
C1 | 0.7300 (2) | 0.16119 (18) | −0.0073 (2) | 0.0626 (6) | |
H1B | 0.7728 | 0.1297 | −0.0592 | 0.075* | |
C2 | 0.6319 (2) | 0.1080 (2) | 0.0109 (3) | 0.0782 (8) | |
H2A | 0.6096 | 0.0412 | −0.0287 | 0.094* | |
C3 | 0.5677 (2) | 0.1536 (2) | 0.0871 (3) | 0.0752 (7) | |
H3A | 0.5019 | 0.1179 | 0.0984 | 0.090* | |
C4 | 0.60071 (18) | 0.2515 (2) | 0.1462 (2) | 0.0656 (6) | |
H4A | 0.5577 | 0.2823 | 0.1984 | 0.079* | |
C5 | 0.69881 (17) | 0.30514 (18) | 0.1281 (2) | 0.0527 (5) | |
H5A | 0.7207 | 0.3718 | 0.1684 | 0.063* | |
C6 | 0.76424 (15) | 0.26070 (16) | 0.05127 (17) | 0.0431 (5) | |
C7 | 0.86758 (16) | 0.32136 (16) | 0.02265 (18) | 0.0443 (5) | |
H7A | 0.9261 | 0.2683 | 0.0105 | 0.053* | |
C8 | 0.83397 (17) | 0.39762 (16) | −0.09041 (18) | 0.0477 (5) | |
H8A | 0.8885 | 0.3926 | −0.1435 | 0.057* | |
H8B | 0.7580 | 0.3803 | −0.1386 | 0.057* | |
C9 | 0.83706 (14) | 0.51037 (15) | −0.03101 (16) | 0.0399 (4) | |
C10 | 0.96804 (16) | 0.37385 (19) | 0.23899 (19) | 0.0510 (5) | |
C11 | 1.0003 (2) | 0.4665 (2) | 0.3291 (2) | 0.0692 (7) | |
H11A | 1.0359 | 0.4372 | 0.4091 | 0.104* | |
H11B | 0.9328 | 0.5072 | 0.3353 | 0.104* | |
H11C | 1.0530 | 0.5149 | 0.3010 | 0.104* | |
C12 | 0.79158 (15) | 0.61317 (16) | −0.09385 (16) | 0.0401 (4) | |
C13 | 0.72450 (17) | 0.61213 (18) | −0.21421 (17) | 0.0488 (5) | |
H13A | 0.7113 | 0.5453 | −0.2567 | 0.059* | |
C14 | 0.67681 (18) | 0.70857 (18) | −0.27246 (18) | 0.0530 (5) | |
H14A | 0.6325 | 0.7061 | −0.3529 | 0.064* | |
C15 | 0.69585 (17) | 0.80830 (17) | −0.20962 (18) | 0.0494 (5) | |
C16 | 0.76478 (17) | 0.81081 (18) | −0.09011 (19) | 0.0532 (5) | |
H16A | 0.7792 | 0.8779 | −0.0485 | 0.064* | |
C17 | 0.81149 (16) | 0.71543 (16) | −0.03326 (18) | 0.0471 (5) | |
H17A | 0.8570 | 0.7187 | 0.0466 | 0.057* | |
C18 | 0.5717 (2) | 0.9082 (2) | −0.3733 (2) | 0.0783 (8) | |
H18A | 0.5455 | 0.9823 | −0.3944 | 0.117* | |
H18B | 0.5074 | 0.8618 | −0.3696 | 0.117* | |
H18C | 0.6096 | 0.8804 | −0.4352 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0631 (10) | 0.0666 (11) | 0.0712 (10) | −0.0005 (8) | −0.0030 (8) | 0.0254 (8) |
O2 | 0.0663 (10) | 0.0570 (10) | 0.0716 (10) | 0.0100 (8) | −0.0048 (8) | 0.0143 (8) |
N1 | 0.0375 (8) | 0.0435 (9) | 0.0456 (9) | −0.0041 (7) | 0.0007 (7) | 0.0041 (7) |
N2 | 0.0384 (8) | 0.0437 (9) | 0.0470 (9) | −0.0048 (7) | 0.0000 (7) | 0.0046 (7) |
C1 | 0.0595 (14) | 0.0490 (13) | 0.0776 (15) | −0.0063 (11) | 0.0114 (12) | −0.0100 (11) |
C2 | 0.0694 (16) | 0.0541 (15) | 0.105 (2) | −0.0233 (13) | 0.0062 (15) | −0.0089 (14) |
C3 | 0.0481 (13) | 0.0747 (18) | 0.0990 (19) | −0.0217 (12) | 0.0076 (13) | 0.0118 (15) |
C4 | 0.0459 (12) | 0.0758 (17) | 0.0774 (16) | −0.0049 (12) | 0.0188 (11) | 0.0067 (13) |
C5 | 0.0440 (11) | 0.0522 (13) | 0.0616 (12) | −0.0060 (9) | 0.0107 (9) | −0.0019 (10) |
C6 | 0.0370 (9) | 0.0397 (11) | 0.0489 (10) | −0.0001 (8) | 0.0016 (8) | 0.0069 (8) |
C7 | 0.0379 (10) | 0.0419 (11) | 0.0521 (11) | 0.0007 (8) | 0.0079 (8) | 0.0006 (8) |
C8 | 0.0492 (11) | 0.0473 (12) | 0.0460 (11) | −0.0051 (9) | 0.0095 (9) | 0.0003 (9) |
C9 | 0.0321 (9) | 0.0441 (11) | 0.0425 (10) | −0.0057 (8) | 0.0061 (7) | 0.0003 (8) |
C10 | 0.0370 (10) | 0.0632 (14) | 0.0498 (11) | −0.0050 (9) | 0.0028 (8) | 0.0137 (10) |
C11 | 0.0683 (15) | 0.0847 (18) | 0.0473 (12) | −0.0088 (13) | −0.0032 (10) | 0.0065 (12) |
C12 | 0.0330 (9) | 0.0458 (11) | 0.0402 (9) | −0.0024 (8) | 0.0055 (7) | 0.0018 (8) |
C13 | 0.0491 (11) | 0.0501 (12) | 0.0433 (10) | −0.0017 (9) | 0.0016 (9) | −0.0031 (9) |
C14 | 0.0508 (12) | 0.0628 (14) | 0.0401 (10) | 0.0021 (10) | −0.0017 (8) | 0.0038 (10) |
C15 | 0.0410 (10) | 0.0515 (13) | 0.0542 (12) | 0.0045 (9) | 0.0071 (9) | 0.0109 (9) |
C16 | 0.0477 (11) | 0.0469 (12) | 0.0599 (13) | −0.0003 (9) | 0.0010 (9) | −0.0037 (9) |
C17 | 0.0407 (10) | 0.0485 (12) | 0.0464 (11) | −0.0023 (9) | −0.0028 (8) | −0.0008 (9) |
C18 | 0.0751 (17) | 0.0790 (18) | 0.0704 (16) | 0.0155 (14) | −0.0064 (13) | 0.0265 (13) |
Geometric parameters (Å, º) top
O1—C10 | 1.226 (3) | C8—C9 | 1.510 (3) |
O2—C15 | 1.377 (2) | C8—H8A | 0.9700 |
O2—C18 | 1.431 (3) | C8—H8B | 0.9700 |
N1—C9 | 1.291 (2) | C9—C12 | 1.468 (3) |
N1—N2 | 1.399 (2) | C10—C11 | 1.492 (3) |
N2—C10 | 1.363 (3) | C11—H11A | 0.9600 |
N2—C7 | 1.471 (3) | C11—H11B | 0.9600 |
C1—C6 | 1.385 (3) | C11—H11C | 0.9600 |
C1—C2 | 1.391 (3) | C12—C13 | 1.394 (3) |
C1—H1B | 0.9300 | C12—C17 | 1.401 (3) |
C2—C3 | 1.372 (4) | C13—C14 | 1.392 (3) |
C2—H2A | 0.9300 | C13—H13A | 0.9300 |
C3—C4 | 1.369 (4) | C14—C15 | 1.385 (3) |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—C5 | 1.393 (3) | C15—C16 | 1.395 (3) |
C4—H4A | 0.9300 | C16—C17 | 1.372 (3) |
C5—C6 | 1.383 (3) | C16—H16A | 0.9300 |
C5—H5A | 0.9300 | C17—H17A | 0.9300 |
C6—C7 | 1.529 (3) | C18—H18A | 0.9600 |
C7—C8 | 1.533 (3) | C18—H18B | 0.9600 |
C7—H7A | 0.9800 | C18—H18C | 0.9600 |
| | | |
C15—O2—C18 | 117.33 (18) | N1—C9—C8 | 113.35 (16) |
C9—N1—N2 | 107.82 (15) | C12—C9—C8 | 125.98 (16) |
C10—N2—N1 | 122.00 (17) | O1—C10—N2 | 119.6 (2) |
C10—N2—C7 | 124.52 (17) | O1—C10—C11 | 123.33 (19) |
N1—N2—C7 | 112.45 (14) | N2—C10—C11 | 117.03 (19) |
C6—C1—C2 | 120.4 (2) | C10—C11—H11A | 109.5 |
C6—C1—H1B | 119.8 | C10—C11—H11B | 109.5 |
C2—C1—H1B | 119.8 | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 120.4 (2) | C10—C11—H11C | 109.5 |
C3—C2—H2A | 119.8 | H11A—C11—H11C | 109.5 |
C1—C2—H2A | 119.8 | H11B—C11—H11C | 109.5 |
C4—C3—C2 | 119.9 (2) | C13—C12—C17 | 117.73 (17) |
C4—C3—H3A | 120.1 | C13—C12—C9 | 121.27 (17) |
C2—C3—H3A | 120.1 | C17—C12—C9 | 120.97 (16) |
C3—C4—C5 | 119.9 (2) | C14—C13—C12 | 121.67 (19) |
C3—C4—H4A | 120.1 | C14—C13—H13A | 119.2 |
C5—C4—H4A | 120.1 | C12—C13—H13A | 119.2 |
C6—C5—C4 | 121.0 (2) | C15—C14—C13 | 119.47 (18) |
C6—C5—H5A | 119.5 | C15—C14—H14A | 120.3 |
C4—C5—H5A | 119.5 | C13—C14—H14A | 120.3 |
C5—C6—C1 | 118.36 (19) | O2—C15—C14 | 125.05 (18) |
C5—C6—C7 | 122.18 (18) | O2—C15—C16 | 115.52 (19) |
C1—C6—C7 | 119.33 (18) | C14—C15—C16 | 119.42 (19) |
N2—C7—C6 | 112.04 (15) | C17—C16—C15 | 120.77 (19) |
N2—C7—C8 | 101.03 (15) | C17—C16—H16A | 119.6 |
C6—C7—C8 | 112.18 (16) | C15—C16—H16A | 119.6 |
N2—C7—H7A | 110.4 | C16—C17—C12 | 120.91 (18) |
C6—C7—H7A | 110.4 | C16—C17—H17A | 119.5 |
C8—C7—H7A | 110.4 | C12—C17—H17A | 119.5 |
C9—C8—C7 | 102.24 (15) | O2—C18—H18A | 109.5 |
C9—C8—H8A | 111.3 | O2—C18—H18B | 109.5 |
C7—C8—H8A | 111.3 | H18A—C18—H18B | 109.5 |
C9—C8—H8B | 111.3 | O2—C18—H18C | 109.5 |
C7—C8—H8B | 111.3 | H18A—C18—H18C | 109.5 |
H8A—C8—H8B | 109.2 | H18B—C18—H18C | 109.5 |
N1—C9—C12 | 120.67 (16) | | |
| | | |
C9—N1—N2—C10 | −178.39 (16) | C7—C8—C9—N1 | 12.8 (2) |
C9—N1—N2—C7 | −9.5 (2) | C7—C8—C9—C12 | −167.83 (16) |
C6—C1—C2—C3 | 0.1 (4) | N1—N2—C10—O1 | 174.19 (17) |
C1—C2—C3—C4 | −0.5 (4) | C7—N2—C10—O1 | 6.6 (3) |
C2—C3—C4—C5 | 0.5 (4) | N1—N2—C10—C11 | −5.3 (3) |
C3—C4—C5—C6 | −0.2 (4) | C7—N2—C10—C11 | −172.86 (18) |
C4—C5—C6—C1 | −0.1 (3) | N1—C9—C12—C13 | −170.94 (17) |
C4—C5—C6—C7 | 175.73 (19) | C8—C9—C12—C13 | 9.7 (3) |
C2—C1—C6—C5 | 0.2 (3) | N1—C9—C12—C17 | 7.2 (3) |
C2—C1—C6—C7 | −175.8 (2) | C8—C9—C12—C17 | −172.14 (17) |
C10—N2—C7—C6 | 65.6 (2) | C17—C12—C13—C14 | −1.1 (3) |
N1—N2—C7—C6 | −102.96 (17) | C9—C12—C13—C14 | 177.10 (18) |
C10—N2—C7—C8 | −174.77 (17) | C12—C13—C14—C15 | −0.2 (3) |
N1—N2—C7—C8 | 16.63 (19) | C18—O2—C15—C14 | 3.9 (3) |
C5—C6—C7—N2 | 24.1 (2) | C18—O2—C15—C16 | −175.16 (19) |
C1—C6—C7—N2 | −160.08 (18) | C13—C14—C15—O2 | −177.50 (19) |
C5—C6—C7—C8 | −88.7 (2) | C13—C14—C15—C16 | 1.5 (3) |
C1—C6—C7—C8 | 87.1 (2) | O2—C15—C16—C17 | 177.56 (18) |
N2—C7—C8—C9 | −16.27 (17) | C14—C15—C16—C17 | −1.6 (3) |
C6—C7—C8—C9 | 103.22 (18) | C15—C16—C17—C12 | 0.2 (3) |
N2—N1—C9—C12 | 177.86 (15) | C13—C12—C17—C16 | 1.1 (3) |
N2—N1—C9—C8 | −2.7 (2) | C9—C12—C17—C16 | −177.12 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O1i | 0.97 | 2.64 | 3.375 (3) | 133 |
C17—H17A···O1ii | 0.93 | 2.57 | 3.460 (3) | 161 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, y+1/2, −z+1/2. |