The title compound, C15H12N2O3·C2H6O, was synthesized by the condensation of 3,4-(methylenedioxy)benzaldehyde with benzoylhydrazine. The molecule deviates more from planarity than is usual for hydrazones. In the crystal structure, hydrogen bonds link 3,4-(methylenedioxy)benzaldehyde benzoylhydrazone molecules to ethanol solvent molecules; aromatic stacking interactions are also found.
Supporting information
CCDC reference: 257209
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.136
- Data-to-parameter ratio = 9.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.94 Sigma
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.83
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT480_ALERT_4_C Long H...A H-Bond Reported H02 .. N1 .. 2.64 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C2 H6 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3,4-(Methylenedioxy)benzaldehyde benzoylhydrazone ethanol solvate
top
Crystal data top
C15H12N2O3·C2H6O | F(000) = 664 |
Mr = 314.33 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 881 reflections |
a = 11.163 (4) Å | θ = 3.2–22.7° |
b = 6.651 (2) Å | µ = 0.10 mm−1 |
c = 21.519 (7) Å | T = 297 K |
β = 100.015 (6)° | Block, colourless |
V = 1573.3 (9) Å3 | 0.22 × 0.18 × 0.14 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 1746 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
φ and ω scans | h = −11→13 |
7720 measured reflections | k = −7→5 |
2762 independent reflections | l = −25→25 |
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)] = 0.045 | All H-atom parameters refined |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0713P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2762 reflections | Δρmax = 0.19 e Å−3 |
281 parameters | Δρmin = −0.17 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: 0.0047 (16) |
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 | |
N1 | 0.85934 (17) | 0.8259 (3) | 0.14809 (9) | 0.0430 (5) | |
N2 | 0.75280 (17) | 0.9343 (3) | 0.13096 (10) | 0.0427 (5) | |
H2 | 0.760 (2) | 1.067 (4) | 0.1306 (11) | 0.047 (7)* | |
O1 | 0.64269 (15) | 0.6488 (3) | 0.12045 (9) | 0.0591 (5) | |
O2 | 0.82138 (17) | 1.3539 (3) | 0.10781 (9) | 0.0525 (5) | |
H02 | 0.789 (3) | 1.454 (6) | 0.1182 (19) | 0.135 (17)* | |
O10 | 1.39810 (14) | 0.5473 (3) | 0.24305 (8) | 0.0560 (5) | |
O20 | 1.24552 (15) | 0.3706 (3) | 0.17998 (9) | 0.0676 (6) | |
C10 | 1.3678 (3) | 0.3604 (5) | 0.21264 (19) | 0.0656 (9) | |
H10A | 1.419 (3) | 0.335 (5) | 0.1825 (14) | 0.081 (10)* | |
H1OB | 1.374 (3) | 0.245 (5) | 0.2440 (15) | 0.089 (11)* | |
C1 | 0.9509 (2) | 0.9255 (4) | 0.17599 (11) | 0.0409 (6) | |
H1 | 0.940 (2) | 1.067 (4) | 0.1851 (11) | 0.059 (8)* | |
C2 | 0.6473 (2) | 0.8327 (4) | 0.11629 (11) | 0.0406 (6) | |
C3 | 0.8491 (3) | 1.3880 (5) | 0.04670 (14) | 0.0608 (8) | |
H31 | 0.884 (3) | 1.527 (5) | 0.0467 (13) | 0.084 (10)* | |
H32 | 0.775 (3) | 1.387 (4) | 0.0164 (13) | 0.076 (9)* | |
C4 | 0.9388 (4) | 1.2373 (7) | 0.0337 (2) | 0.0788 (11) | |
H41 | 0.956 (3) | 1.251 (5) | −0.0078 (18) | 0.106 (12)* | |
H42 | 1.011 (3) | 1.251 (5) | 0.0641 (16) | 0.100 (13)* | |
H43 | 0.913 (3) | 1.094 (5) | 0.0348 (15) | 0.098 (12)* | |
C11 | 1.0687 (2) | 0.8295 (4) | 0.19494 (10) | 0.0383 (6) | |
C12 | 1.1607 (2) | 0.9314 (4) | 0.23382 (12) | 0.0462 (7) | |
H12 | 1.145 (2) | 1.060 (4) | 0.2467 (11) | 0.057 (8)* | |
C13 | 1.2748 (2) | 0.8479 (4) | 0.25355 (12) | 0.0486 (7) | |
H13 | 1.332 (2) | 0.919 (4) | 0.2795 (12) | 0.060 (8)* | |
C14 | 1.2936 (2) | 0.6602 (4) | 0.23203 (11) | 0.0406 (6) | |
C15 | 1.2025 (2) | 0.5556 (4) | 0.19403 (11) | 0.0419 (6) | |
C16 | 1.0901 (2) | 0.6338 (4) | 0.17470 (12) | 0.0427 (6) | |
H16 | 1.028 (2) | 0.556 (4) | 0.1508 (11) | 0.053 (7)* | |
C21 | 0.53558 (19) | 0.9547 (4) | 0.09636 (10) | 0.0368 (6) | |
C22 | 0.5360 (2) | 1.1459 (4) | 0.07103 (12) | 0.0472 (6) | |
H22 | 0.611 (2) | 1.206 (4) | 0.0696 (11) | 0.057 (8)* | |
C23 | 0.4275 (2) | 1.2468 (5) | 0.05109 (13) | 0.0575 (8) | |
H23 | 0.428 (2) | 1.376 (4) | 0.0323 (12) | 0.069 (9)* | |
C24 | 0.3191 (3) | 1.1594 (5) | 0.05718 (13) | 0.0587 (8) | |
H24 | 0.241 (3) | 1.230 (5) | 0.0453 (14) | 0.091 (10)* | |
C25 | 0.3179 (3) | 0.9718 (5) | 0.08352 (13) | 0.0586 (8) | |
H25 | 0.241 (2) | 0.914 (4) | 0.0896 (11) | 0.065 (8)* | |
C26 | 0.4249 (2) | 0.8695 (4) | 0.10231 (12) | 0.0506 (7) | |
H26 | 0.424 (2) | 0.737 (4) | 0.1178 (11) | 0.055 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0338 (11) | 0.0356 (11) | 0.0581 (13) | 0.0079 (10) | 0.0039 (9) | 0.0052 (10) |
N2 | 0.0358 (12) | 0.0290 (12) | 0.0614 (14) | 0.0057 (10) | 0.0032 (9) | 0.0031 (10) |
O1 | 0.0491 (11) | 0.0348 (11) | 0.0899 (14) | 0.0019 (9) | 0.0022 (9) | 0.0104 (10) |
O2 | 0.0591 (12) | 0.0382 (11) | 0.0616 (12) | 0.0026 (9) | 0.0146 (9) | 0.0024 (9) |
O10 | 0.0339 (10) | 0.0574 (12) | 0.0723 (13) | 0.0086 (9) | −0.0034 (8) | −0.0027 (10) |
O20 | 0.0434 (11) | 0.0511 (12) | 0.1007 (15) | 0.0142 (9) | −0.0082 (10) | −0.0239 (11) |
C10 | 0.0457 (18) | 0.061 (2) | 0.084 (2) | 0.0148 (16) | −0.0061 (16) | −0.0117 (19) |
C1 | 0.0410 (15) | 0.0339 (14) | 0.0481 (14) | 0.0047 (12) | 0.0089 (11) | 0.0026 (12) |
C2 | 0.0408 (15) | 0.0355 (15) | 0.0454 (14) | 0.0020 (12) | 0.0071 (11) | 0.0059 (12) |
C3 | 0.0596 (19) | 0.057 (2) | 0.064 (2) | −0.0033 (17) | 0.0069 (16) | 0.0079 (16) |
C4 | 0.073 (3) | 0.087 (3) | 0.083 (3) | 0.003 (2) | 0.032 (2) | −0.006 (2) |
C11 | 0.0359 (13) | 0.0352 (14) | 0.0438 (14) | 0.0004 (11) | 0.0075 (10) | 0.0030 (11) |
C12 | 0.0456 (16) | 0.0351 (15) | 0.0568 (16) | 0.0005 (13) | 0.0057 (12) | −0.0044 (13) |
C13 | 0.0400 (15) | 0.0471 (16) | 0.0549 (16) | −0.0056 (14) | −0.0018 (12) | −0.0083 (13) |
C14 | 0.0325 (13) | 0.0423 (15) | 0.0461 (14) | −0.0005 (12) | 0.0042 (10) | 0.0057 (12) |
C15 | 0.0372 (14) | 0.0360 (14) | 0.0518 (15) | 0.0021 (12) | 0.0063 (11) | −0.0034 (12) |
C16 | 0.0345 (14) | 0.0388 (15) | 0.0516 (16) | −0.0023 (12) | −0.0009 (11) | −0.0069 (12) |
C21 | 0.0359 (13) | 0.0382 (14) | 0.0360 (13) | 0.0015 (11) | 0.0055 (10) | −0.0017 (11) |
C22 | 0.0386 (15) | 0.0432 (16) | 0.0589 (16) | 0.0024 (13) | 0.0059 (12) | 0.0082 (13) |
C23 | 0.0494 (17) | 0.0548 (19) | 0.0663 (19) | 0.0147 (15) | 0.0049 (13) | 0.0131 (16) |
C24 | 0.0387 (16) | 0.074 (2) | 0.0606 (18) | 0.0172 (16) | 0.0018 (13) | −0.0006 (16) |
C25 | 0.0366 (16) | 0.074 (2) | 0.0656 (19) | −0.0012 (16) | 0.0100 (13) | 0.0030 (16) |
C26 | 0.0452 (16) | 0.0493 (18) | 0.0574 (17) | −0.0012 (14) | 0.0090 (12) | 0.0060 (14) |
Geometric parameters (Å, º) top
N1—C1 | 1.277 (3) | C4—H43 | 1.00 (3) |
N1—N2 | 1.385 (3) | C11—C12 | 1.384 (3) |
N2—C2 | 1.347 (3) | C11—C16 | 1.406 (3) |
N2—H2 | 0.88 (2) | C12—C13 | 1.386 (4) |
O1—C2 | 1.228 (3) | C12—H12 | 0.92 (2) |
O2—C3 | 1.421 (3) | C13—C14 | 1.360 (3) |
O2—H02 | 0.81 (4) | C13—H13 | 0.91 (3) |
O10—C14 | 1.373 (3) | C14—C15 | 1.377 (3) |
O10—C10 | 1.418 (3) | C15—C16 | 1.355 (3) |
O20—C15 | 1.374 (3) | C16—H16 | 0.94 (2) |
O20—C10 | 1.424 (3) | C21—C22 | 1.384 (3) |
C10—H10A | 0.95 (3) | C21—C26 | 1.385 (3) |
C10—H1OB | 1.02 (3) | C22—C23 | 1.385 (3) |
C1—C11 | 1.455 (3) | C22—H22 | 0.93 (2) |
C1—H1 | 0.97 (3) | C23—C24 | 1.369 (4) |
C2—C21 | 1.488 (3) | C23—H23 | 0.95 (3) |
C3—C4 | 1.477 (5) | C24—C25 | 1.372 (4) |
C3—H31 | 1.01 (3) | C24—H24 | 0.98 (3) |
C3—H32 | 0.96 (3) | C25—C26 | 1.373 (4) |
C4—H41 | 0.95 (4) | C25—H25 | 0.97 (2) |
C4—H42 | 0.95 (3) | C26—H26 | 0.94 (2) |
| | | |
C1—N1—N2 | 115.8 (2) | C11—C12—C13 | 122.3 (3) |
C2—N2—N1 | 118.5 (2) | C11—C12—H12 | 118.2 (15) |
C2—N2—H2 | 125.4 (15) | C13—C12—H12 | 119.5 (15) |
N1—N2—H2 | 116.2 (15) | C14—C13—C12 | 116.9 (3) |
C3—O2—H02 | 108 (3) | C14—C13—H13 | 123.4 (16) |
C14—O10—C10 | 105.81 (19) | C12—C13—H13 | 119.7 (16) |
C15—O20—C10 | 106.0 (2) | C13—C14—O10 | 128.3 (2) |
O10—C10—O20 | 108.5 (2) | C13—C14—C15 | 121.6 (2) |
O10—C10—H10A | 110.1 (19) | O10—C14—C15 | 110.1 (2) |
O20—C10—H10A | 108.2 (18) | C16—C15—O20 | 128.0 (2) |
O10—C10—H1OB | 111.8 (18) | C16—C15—C14 | 122.5 (2) |
O20—C10—H1OB | 108.4 (18) | O20—C15—C14 | 109.4 (2) |
H10A—C10—H1OB | 110 (3) | C15—C16—C11 | 117.2 (2) |
N1—C1—C11 | 121.0 (2) | C15—C16—H16 | 120.9 (15) |
N1—C1—H1 | 118.8 (14) | C11—C16—H16 | 121.8 (14) |
C11—C1—H1 | 120.1 (14) | C22—C21—C26 | 118.4 (2) |
O1—C2—N2 | 122.0 (2) | C22—C21—C2 | 123.7 (2) |
O1—C2—C21 | 121.4 (2) | C26—C21—C2 | 117.8 (2) |
N2—C2—C21 | 116.7 (2) | C21—C22—C23 | 120.3 (3) |
O2—C3—C4 | 109.4 (3) | C21—C22—H22 | 118.2 (15) |
O2—C3—H31 | 107.2 (16) | C23—C22—H22 | 121.4 (15) |
C4—C3—H31 | 110.2 (16) | C24—C23—C22 | 120.3 (3) |
O2—C3—H32 | 109.1 (16) | C24—C23—H23 | 119.8 (16) |
C4—C3—H32 | 113.3 (17) | C22—C23—H23 | 119.9 (16) |
H31—C3—H32 | 107 (2) | C23—C24—C25 | 119.9 (3) |
C3—C4—H41 | 112 (2) | C23—C24—H24 | 122.2 (17) |
C3—C4—H42 | 109 (2) | C25—C24—H24 | 117.9 (17) |
H41—C4—H42 | 111 (3) | C24—C25—C26 | 120.1 (3) |
C3—C4—H43 | 115.8 (19) | C24—C25—H25 | 119.5 (15) |
H41—C4—H43 | 103 (3) | C26—C25—H25 | 120.4 (15) |
H42—C4—H43 | 107 (3) | C25—C26—C21 | 120.9 (3) |
C12—C11—C16 | 119.5 (2) | C25—C26—H26 | 120.5 (15) |
C12—C11—C1 | 119.6 (2) | C21—C26—H26 | 118.5 (15) |
C16—C11—C1 | 120.9 (2) | | |
| | | |
C1—N1—N2—C2 | −163.5 (2) | C13—C14—C15—O20 | −179.2 (2) |
C14—O10—C10—O20 | 3.8 (3) | O10—C14—C15—O20 | 0.7 (3) |
C15—O20—C10—O10 | −3.4 (4) | O20—C15—C16—C11 | −179.1 (2) |
N2—N1—C1—C11 | −178.47 (19) | C14—C15—C16—C11 | 0.1 (4) |
N1—N2—C2—O1 | 3.3 (4) | C12—C11—C16—C15 | −1.0 (3) |
N1—N2—C2—C21 | −178.28 (18) | C1—C11—C16—C15 | 179.5 (2) |
N1—C1—C11—C12 | −169.6 (2) | O1—C2—C21—C22 | −157.9 (2) |
N1—C1—C11—C16 | 9.8 (4) | N2—C2—C21—C22 | 23.7 (3) |
C16—C11—C12—C13 | 0.5 (4) | O1—C2—C21—C26 | 20.6 (3) |
C1—C11—C12—C13 | 179.9 (2) | N2—C2—C21—C26 | −157.8 (2) |
C11—C12—C13—C14 | 1.0 (4) | C26—C21—C22—C23 | −1.2 (4) |
C12—C13—C14—O10 | 178.2 (2) | C2—C21—C22—C23 | 177.2 (2) |
C12—C13—C14—C15 | −2.0 (4) | C21—C22—C23—C24 | 1.0 (4) |
C10—O10—C14—C13 | 177.1 (3) | C22—C23—C24—C25 | 0.4 (4) |
C10—O10—C14—C15 | −2.8 (3) | C23—C24—C25—C26 | −1.6 (4) |
C10—O20—C15—C16 | −179.0 (3) | C24—C25—C26—C21 | 1.4 (4) |
C10—O20—C15—C14 | 1.7 (3) | C22—C21—C26—C25 | 0.0 (4) |
C13—C14—C15—C16 | 1.5 (4) | C2—C21—C26—C25 | −178.5 (2) |
O10—C14—C15—C16 | −178.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.88 (2) | 2.11 (2) | 2.959 (3) | 159 (2) |
O2—H02···N1i | 0.81 (4) | 2.64 (4) | 3.265 (3) | 135 (3) |
O2—H02···O1i | 0.81 (4) | 2.09 (4) | 2.844 (3) | 155 (4) |
Symmetry code: (i) x, y+1, z. |