The title compound, C
17H
18N
2O
3, was synthesized by the reaction of ethyl 3-(3,4-dimethoxyphenyl)acrylate and phenylhydrazine. There are intermolecular N—H
O and C—H
O hydrogen bonds, and also C—H
π interactions.
Supporting information
CCDC reference: 236094
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.065
- wR factor = 0.275
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.777 0.982
Tmin' and Tmax expected: 0.964 0.982
RR' = 0.806
Please check that your absorption correction is appropriate.
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.275
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81
PLAT084_ALERT_2_C High R2 Value .................................. 0.28
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C17 H18 N2 O3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please provide; software used to prepare material for publication: SHELXS97.
5-(3,4-dimethoxyphenyl)-1-phenylpyrazolidin-3-one
top
Crystal data top
C17H18N2O3 | Z = 2 |
Mr = 298.33 | F(000) = 316 |
Triclinic, P1 | Dx = 1.280 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.011 (2) Å | Cell parameters from 25 reflections |
b = 9.403 (2) Å | θ = 10–13° |
c = 11.621 (2) Å | µ = 0.09 mm−1 |
α = 66.49 (3)° | T = 293 K |
β = 67.67 (3)° | Block, colourless |
γ = 62.05 (3)° | 0.4 × 0.3 × 0.2 mm |
V = 774.6 (4) Å3 | |
Data collection top
Nonius CAD-4/PC diffractometer | 2090 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.070 |
Graphite monochromator | θmax = 25°, θmin = 2.0° |
ω/2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −9→11 |
Tmin = 0.777, Tmax = 0.982 | l = −12→13 |
2902 measured reflections | 3 standard reflections every 200 reflections |
2715 independent reflections | intensity decay: 0.9% |
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)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.275 | w = 1/[σ2(Fo2) + (0.16P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max = 0.001 |
2715 reflections | Δρmax = 0.27 e Å−3 |
204 parameters | Δρmin = −0.30 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: 0.058 (17) |
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 | −0.3102 (3) | 1.3251 (3) | −0.0519 (3) | 0.0620 (8) | |
O2 | 0.1139 (4) | 0.7080 (3) | 0.4494 (2) | 0.0620 (8) | |
O3 | −0.1625 (4) | 0.7390 (3) | 0.6302 (3) | 0.0704 (9) | |
N1 | −0.3602 (4) | 1.4563 (4) | 0.0948 (3) | 0.0513 (8) | |
N2 | −0.2882 (3) | 1.4402 (3) | 0.1907 (3) | 0.0438 (7) | |
C1 | −0.2652 (4) | 1.3452 (4) | 0.0268 (3) | 0.0466 (8) | |
C2 | −0.0951 (4) | 1.2487 (5) | 0.0636 (3) | 0.0514 (9) | |
H2A | −0.0057 | 1.2859 | −0.0027 | 0.062* | |
H2B | −0.0602 | 1.1299 | 0.0765 | 0.062* | |
C3 | −0.1280 (4) | 1.2858 (4) | 0.1900 (3) | 0.0424 (8) | |
H3A | −0.0320 | 1.3112 | 0.1859 | 0.051* | |
C4 | −0.2773 (4) | 1.5864 (4) | 0.1881 (3) | 0.0413 (8) | |
C5 | −0.3492 (4) | 1.7418 (4) | 0.1071 (3) | 0.0499 (9) | |
H5A | −0.3996 | 1.7524 | 0.0461 | 0.060* | |
C6 | −0.3452 (5) | 1.8818 (5) | 0.1183 (5) | 0.0671 (11) | |
H6A | −0.3939 | 1.9864 | 0.0645 | 0.080* | |
C7 | −0.2706 (6) | 1.8684 (6) | 0.2073 (5) | 0.0725 (13) | |
H7A | −0.2690 | 1.9629 | 0.2142 | 0.087* | |
C8 | −0.1988 (6) | 1.7139 (6) | 0.2859 (4) | 0.0708 (12) | |
H8A | −0.1468 | 1.7037 | 0.3458 | 0.085* | |
C9 | −0.2020 (5) | 1.5765 (5) | 0.2778 (4) | 0.0568 (10) | |
H9A | −0.1534 | 1.4730 | 0.3330 | 0.068* | |
C10 | −0.1475 (4) | 1.1442 (4) | 0.3094 (3) | 0.0375 (7) | |
C11 | −0.2961 (4) | 1.1583 (4) | 0.4069 (3) | 0.0491 (9) | |
H11A | −0.3906 | 1.2592 | 0.4003 | 0.059* | |
C12 | −0.3073 (5) | 1.0244 (5) | 0.5151 (3) | 0.0538 (9) | |
H12A | −0.4096 | 1.0355 | 0.5792 | 0.065* | |
C13 | −0.1684 (4) | 0.8765 (4) | 0.5275 (3) | 0.0478 (8) | |
C14 | −0.0149 (4) | 0.8597 (4) | 0.4288 (3) | 0.0438 (8) | |
C15 | −0.0074 (4) | 0.9924 (4) | 0.3217 (3) | 0.0429 (8) | |
H15A | 0.0934 | 0.9806 | 0.2561 | 0.052* | |
C16 | −0.3095 (7) | 0.7454 (7) | 0.7307 (5) | 0.1002 (19) | |
H16A | −0.2872 | 0.6405 | 0.7960 | 0.150* | |
H16B | −0.4035 | 0.7668 | 0.6983 | 0.150* | |
H16C | −0.3394 | 0.8334 | 0.7672 | 0.150* | |
C17 | 0.2727 (6) | 0.6835 (6) | 0.3544 (4) | 0.0834 (15) | |
H17A | 0.3525 | 0.5711 | 0.3802 | 0.125* | |
H17B | 0.3202 | 0.7609 | 0.3454 | 0.125* | |
H17C | 0.2528 | 0.7018 | 0.2732 | 0.125* | |
H1 | −0.484 (7) | 1.509 (6) | 0.102 (5) | 0.089 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0599 (16) | 0.0665 (17) | 0.0646 (16) | −0.0085 (13) | −0.0313 (13) | −0.0254 (13) |
O2 | 0.0620 (16) | 0.0437 (14) | 0.0506 (14) | 0.0038 (11) | −0.0186 (12) | −0.0083 (11) |
O3 | 0.0672 (18) | 0.0606 (17) | 0.0556 (16) | −0.0226 (14) | −0.0165 (13) | 0.0108 (13) |
N1 | 0.0493 (17) | 0.0485 (16) | 0.0646 (19) | −0.0089 (13) | −0.0315 (15) | −0.0178 (14) |
N2 | 0.0463 (15) | 0.0394 (15) | 0.0485 (15) | −0.0143 (12) | −0.0244 (12) | −0.0040 (11) |
C1 | 0.0471 (18) | 0.0451 (18) | 0.0437 (17) | −0.0139 (14) | −0.0161 (14) | −0.0072 (14) |
C2 | 0.0431 (18) | 0.059 (2) | 0.0370 (17) | −0.0115 (15) | −0.0109 (14) | −0.0071 (15) |
C3 | 0.0374 (16) | 0.0394 (17) | 0.0484 (18) | −0.0147 (13) | −0.0157 (13) | −0.0044 (13) |
C4 | 0.0375 (16) | 0.0435 (17) | 0.0407 (16) | −0.0127 (13) | −0.0106 (13) | −0.0111 (13) |
C5 | 0.0466 (18) | 0.0431 (18) | 0.055 (2) | −0.0099 (14) | −0.0216 (15) | −0.0085 (15) |
C6 | 0.058 (2) | 0.040 (2) | 0.093 (3) | −0.0095 (16) | −0.020 (2) | −0.0166 (19) |
C7 | 0.063 (2) | 0.067 (3) | 0.104 (3) | −0.026 (2) | −0.010 (2) | −0.048 (3) |
C8 | 0.075 (3) | 0.084 (3) | 0.075 (3) | −0.031 (2) | −0.022 (2) | −0.038 (2) |
C9 | 0.067 (2) | 0.063 (2) | 0.050 (2) | −0.0261 (19) | −0.0255 (17) | −0.0116 (17) |
C10 | 0.0410 (16) | 0.0377 (16) | 0.0357 (15) | −0.0108 (13) | −0.0164 (12) | −0.0097 (12) |
C11 | 0.0445 (18) | 0.0435 (18) | 0.0480 (19) | −0.0061 (14) | −0.0168 (15) | −0.0089 (15) |
C12 | 0.0437 (18) | 0.058 (2) | 0.0449 (19) | −0.0142 (16) | −0.0070 (14) | −0.0093 (16) |
C13 | 0.0512 (19) | 0.0461 (18) | 0.0425 (18) | −0.0176 (15) | −0.0173 (15) | −0.0035 (14) |
C14 | 0.0492 (18) | 0.0375 (16) | 0.0412 (17) | −0.0065 (14) | −0.0190 (14) | −0.0113 (13) |
C15 | 0.0441 (17) | 0.0458 (18) | 0.0358 (16) | −0.0113 (14) | −0.0134 (13) | −0.0110 (13) |
C16 | 0.081 (3) | 0.098 (4) | 0.073 (3) | −0.039 (3) | −0.012 (3) | 0.023 (3) |
C17 | 0.071 (3) | 0.069 (3) | 0.062 (3) | 0.014 (2) | −0.015 (2) | −0.022 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.236 (4) | C6—H6A | 0.9300 |
O2—C14 | 1.351 (4) | C7—C8 | 1.368 (7) |
O2—C17 | 1.419 (5) | C7—H7A | 0.9300 |
O3—C13 | 1.361 (4) | C8—C9 | 1.346 (6) |
O3—C16 | 1.388 (6) | C8—H8A | 0.9300 |
N1—C1 | 1.324 (5) | C9—H9A | 0.9300 |
N1—N2 | 1.417 (4) | C10—C11 | 1.376 (5) |
N1—H1 | 0.97 (5) | C10—C15 | 1.391 (4) |
N2—C4 | 1.411 (4) | C11—C12 | 1.392 (5) |
N2—C3 | 1.492 (4) | C11—H11A | 0.9300 |
C1—C2 | 1.496 (5) | C12—C13 | 1.366 (5) |
C2—C3 | 1.533 (5) | C12—H12A | 0.9300 |
C2—H2A | 0.9700 | C13—C14 | 1.410 (5) |
C2—H2B | 0.9700 | C14—C15 | 1.373 (5) |
C3—C10 | 1.513 (4) | C15—H15A | 0.9300 |
C3—H3A | 0.9800 | C16—H16A | 0.9600 |
C4—C5 | 1.385 (5) | C16—H16B | 0.9600 |
C4—C9 | 1.398 (5) | C16—H16C | 0.9600 |
C5—C6 | 1.392 (5) | C17—H17A | 0.9600 |
C5—H5A | 0.9300 | C17—H17B | 0.9600 |
C6—C7 | 1.371 (6) | C17—H17C | 0.9600 |
| | | |
C14—O2—C17 | 117.7 (3) | C9—C8—H8A | 119.5 |
C13—O3—C16 | 118.4 (3) | C7—C8—H8A | 119.5 |
C1—N1—N2 | 115.0 (3) | C8—C9—C4 | 121.2 (4) |
C1—N1—H1 | 119 (3) | C8—C9—H9A | 119.4 |
N2—N1—H1 | 121 (3) | C4—C9—H9A | 119.4 |
C4—N2—N1 | 116.1 (2) | C11—C10—C15 | 118.4 (3) |
C4—N2—C3 | 118.2 (2) | C11—C10—C3 | 123.3 (3) |
N1—N2—C3 | 105.6 (2) | C15—C10—C3 | 118.3 (3) |
O1—C1—N1 | 125.9 (3) | C10—C11—C12 | 121.2 (3) |
O1—C1—C2 | 126.6 (3) | C10—C11—H11A | 119.4 |
N1—C1—C2 | 107.5 (3) | C12—C11—H11A | 119.4 |
C1—C2—C3 | 104.3 (3) | C13—C12—C11 | 120.1 (3) |
C1—C2—H2A | 110.9 | C13—C12—H12A | 119.9 |
C3—C2—H2A | 110.9 | C11—C12—H12A | 119.9 |
C1—C2—H2B | 110.9 | O3—C13—C12 | 125.4 (3) |
C3—C2—H2B | 110.9 | O3—C13—C14 | 115.1 (3) |
H2A—C2—H2B | 108.9 | C12—C13—C14 | 119.5 (3) |
N2—C3—C10 | 112.1 (3) | O2—C14—C15 | 125.6 (3) |
N2—C3—C2 | 104.0 (2) | O2—C14—C13 | 114.9 (3) |
C10—C3—C2 | 113.9 (3) | C15—C14—C13 | 119.4 (3) |
N2—C3—H3A | 108.9 | C14—C15—C10 | 121.3 (3) |
C10—C3—H3A | 108.9 | C14—C15—H15A | 119.3 |
C2—C3—H3A | 108.9 | C10—C15—H15A | 119.3 |
C5—C4—C9 | 118.4 (3) | O3—C16—H16A | 109.5 |
C5—C4—N2 | 122.8 (3) | O3—C16—H16B | 109.5 |
C9—C4—N2 | 118.5 (3) | H16A—C16—H16B | 109.5 |
C4—C5—C6 | 119.1 (3) | O3—C16—H16C | 109.5 |
C4—C5—H5A | 120.5 | H16A—C16—H16C | 109.5 |
C6—C5—H5A | 120.5 | H16B—C16—H16C | 109.5 |
C7—C6—C5 | 121.2 (4) | O2—C17—H17A | 109.5 |
C7—C6—H6A | 119.4 | O2—C17—H17B | 109.5 |
C5—C6—H6A | 119.4 | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 119.0 (4) | O2—C17—H17C | 109.5 |
C8—C7—H7A | 120.5 | H17A—C17—H17C | 109.5 |
C6—C7—H7A | 120.5 | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 121.1 (4) | | |
| | | |
C1—N1—N2—C4 | 128.0 (3) | N2—C4—C9—C8 | −175.4 (3) |
C1—N1—N2—C3 | −5.0 (4) | N2—C3—C10—C11 | −0.4 (4) |
N2—N1—C1—O1 | 172.1 (3) | C2—C3—C10—C11 | −118.2 (3) |
N2—N1—C1—C2 | −7.5 (4) | N2—C3—C10—C15 | −179.8 (2) |
O1—C1—C2—C3 | −163.3 (3) | C2—C3—C10—C15 | 62.5 (4) |
N1—C1—C2—C3 | 16.4 (4) | C15—C10—C11—C12 | −0.4 (5) |
C4—N2—C3—C10 | 119.3 (3) | C3—C10—C11—C12 | −179.7 (3) |
N1—N2—C3—C10 | −108.8 (3) | C10—C11—C12—C13 | 1.3 (5) |
C4—N2—C3—C2 | −117.1 (3) | C16—O3—C13—C12 | 1.4 (6) |
N1—N2—C3—C2 | 14.7 (3) | C16—O3—C13—C14 | −179.4 (4) |
C1—C2—C3—N2 | −18.7 (3) | C11—C12—C13—O3 | 178.1 (3) |
C1—C2—C3—C10 | 103.6 (3) | C11—C12—C13—C14 | −1.1 (5) |
N1—N2—C4—C5 | 7.1 (4) | C17—O2—C14—C15 | 1.7 (5) |
C3—N2—C4—C5 | 134.0 (3) | C17—O2—C14—C13 | −179.3 (4) |
N1—N2—C4—C9 | −177.9 (3) | O3—C13—C14—O2 | 1.7 (4) |
C3—N2—C4—C9 | −50.9 (4) | C12—C13—C14—O2 | −179.1 (3) |
C9—C4—C5—C6 | −0.4 (5) | O3—C13—C14—C15 | −179.3 (3) |
N2—C4—C5—C6 | 174.6 (3) | C12—C13—C14—C15 | 0.0 (5) |
C4—C5—C6—C7 | 0.3 (6) | O2—C14—C15—C10 | 179.9 (3) |
C5—C6—C7—C8 | 0.2 (6) | C13—C14—C15—C10 | 1.0 (5) |
C6—C7—C8—C9 | −0.7 (7) | C11—C10—C15—C14 | −0.8 (5) |
C7—C8—C9—C4 | 0.7 (7) | C3—C10—C15—C14 | 178.6 (3) |
C5—C4—C9—C8 | −0.1 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.97 (5) | 1.90 (6) | 2.807 (5) | 155 (5) |
C9—H9A···O2ii | 0.93 | 2.47 | 3.315 (5) | 151 |
C17—H17C···O1iii | 0.96 | 2.52 | 3.432 (5) | 159 |
C2—H2A···Cg1iv | 0.97 | 2.66 | 3.576 (4) | 157 |
Symmetry codes: (i) −x−1, −y+3, −z; (ii) −x, −y+2, −z+1; (iii) −x, −y+2, −z; (iv) −x, −y+3, −z. |