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Acta Cryst. (2007). E63, o3674    [ doi:10.1107/S1600536807037051 ]

4-Methoxybenzaldehyde (phthalazin-1-ylidene)hydrazone

R. J. Butcher, J. P. Jasinski, H. S. Yathirajan, A. M. Vijesh and B. Narayana

Abstract top

The title compound, C16H14N4O, crystallizes with two independent molecules in the asymmetric unit. The phthalazin-1-yl and 4-methoxybenzaldehyde groups are coplanar with each other in each of the independent molecules with angles between their mean planes of 15.4 (4) and 13.3 (9)°. The crystal packing is stabilized by intermolecular N-H...N hydrogen bonding between inverted phthalazin-1-yl groups allowing the independent molecules to be stacked in groups oblique to the ab plane in a zigzag pattern.

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, and antitumor, as well they can be herbicides. Schiff bases have also been employed as ligands for complexation of metal ions. On the industrial scale, they have wide range of applications such as dyes and pigments. A new Schiff base, C16H14N4O, (I), has been synthesized and its crystal structure is reported herein.

Two independent molecules of (I), molecules A and B, Fig. 1, comprise the crystallographic asymmetric unit. The phthalazin-1-yl and 4-methoxybenzaldehyde groups are coplanar with each other in each of the independent molecules with an angle between their mean planes of 15.4 (4) and 13.3 (9) Å in A and B, respectively. These groups are also planar with the hydrazone group, forming torsion angles of N4—N3—C8—N2 [1.8 (2)°] and N4—C9—C10—C11 [14.1 (2)°] for molecule A, and N4—N3—C8—N2 [−6.1 (2)°] and N4—C9—C10—C11 [−2.7 (2)°] for B.

Molecules A and B are linked by intermolecular N—H···N hydrogen bonding interactions (Table 1) between inverted phthalazin-1-yl groups. These stack diagonal to the a axis in a zigzag pattern (Fig. 2).

Related literature top

For related structures, see: Lynch & McClenaghan (2002a,b). For related literature, see: El-Masry et al. (2000); Pandey et al. (1999); Singh & Dash, 1988; Hodnett & Dunn, 1970; Desai et al. (2001); Aydogan et al. (2001); Taggi et al. (2002).

Experimental top

A mixture of 1-hydrazinophthalazine (0.32 g, 0.002 mol) and 4-methoxybenzaldehyde (0.272 g, 0.002 mol) in absolute ethanol (15 ml) containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from acetone (m.p. 419–23 K). Analysis found: C 68.93, H 5.01, N 20.04%; C16H14N4O requires: C 69.05, H 5.07, N 20.13%.

Refinement top

The H atoms were included in the riding model approximation with C—H = 0.94 Å and N—H = 0.87 Å, and with Uiso(H) = 1.18–1.49 Ueq(C,N).

Computing details top

Data collection: CrysAlisPro (Oxford Diffraction, 2007); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX.

Figures top
[Figure 1] Fig. 1. Molecular structure of the two independent molecules in (I), showing atom labelling, 50% probability displacement ellipsoids and N—H···N hydrogen bonds as dashed lines.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the a axis. Dashed lines indicate N—H···N hydrogen bonds.
4-Methoxybenzaldehyde (phthalazin-1-ylidene)hydrazone top
Crystal data top
C16H14N4OF000 = 1168
Mr = 278.31Dx = 1.335 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5610 reflections
a = 12.1351 (8) Åθ = 4.6–32.4º
b = 14.2016 (7) ŵ = 0.09 mm−1
c = 16.0716 (8) ÅT = 203 K
β = 90.012 (6)ºChunk, yellow
V = 2769.7 (3) Å30.55 × 0.41 × 0.37 mm
Z = 8
Data collection top
Oxford Diffraction Gemini R
diffractometer		Rint = 0.035
Radiation source: fine-focus sealed tubeθmax = 32.5º
Monochromator: graphiteθmin = 4.6º
T = 203 Kh = −18→15
φ and ω scansk = −20→20
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		l = −22→24
Tmin = 0.833, Tmax = 1.0002 standard reflections
19111 measured reflections every 50 reflections
8720 independent reflections intensity decay: none
3864 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.180  w = 1/[σ2(Fo2) + (0.0884P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.002
8720 reflectionsΔρmax = 0.27 e Å−3
381 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C16H14N4OV = 2769.7 (3) Å3
Mr = 278.31Z = 8
Monoclinic, P21/cMo Kα
a = 12.1351 (8) ŵ = 0.09 mm−1
b = 14.2016 (7) ÅT = 203 K
c = 16.0716 (8) Å0.55 × 0.41 × 0.37 mm
β = 90.012 (6)º
Data collection top
Oxford Diffraction Gemini R
diffractometer		3864 reflections with I > 2σ(I)
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		Rint = 0.035
Tmin = 0.833, Tmax = 1.0002 standard reflections
19111 measured reflections every 50 reflections
8720 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.057381 parameters
wR(F2) = 0.180H-atom parameters constrained
S = 0.99Δρmax = 0.27 e Å−3
8720 reflectionsΔρmin = −0.23 e Å−3
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 > 2sigma(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
xyzUiso*/Ueq
O1A0.15752 (11)0.62767 (9)−0.14043 (8)0.0594 (4)
O1B−0.24183 (10)1.16684 (8)0.30313 (7)0.0461 (3)
N1A−0.03360 (11)0.99989 (10)0.12664 (9)0.0438 (4)
N2A0.06600 (11)0.97845 (9)0.09289 (8)0.0387 (3)
H2AA0.07110.92460.06740.046*
N3A0.25209 (11)1.00864 (9)0.06025 (8)0.0380 (3)
N4A0.24386 (11)0.92220 (9)0.01902 (8)0.0371 (3)
N1B−0.04553 (11)0.79403 (9)0.04541 (9)0.0420 (3)
N2B−0.14890 (11)0.82042 (9)0.07002 (8)0.0364 (3)
H2BA−0.15560.87660.09100.044*
N3B−0.33832 (11)0.79568 (9)0.09271 (8)0.0375 (3)
N4B−0.33017 (11)0.88110 (9)0.13504 (8)0.0359 (3)
C1A−0.04070 (14)1.07925 (12)0.16550 (11)0.0455 (4)
H1AA−0.10901.09520.18930.055*
C2A0.04879 (14)1.14498 (11)0.17491 (10)0.0388 (4)
C3A0.03655 (16)1.23042 (12)0.21789 (11)0.0462 (4)
H3AA−0.03171.24650.24160.055*
C4A0.12422 (17)1.29002 (12)0.22514 (10)0.0481 (5)
H4AA0.11601.34720.25400.058*
C5A0.22507 (16)1.26718 (12)0.19052 (11)0.0479 (5)
H5AA0.28491.30870.19610.057*
C6A0.23812 (14)1.18376 (11)0.14790 (10)0.0402 (4)
H6AA0.30681.16880.12430.048*
C7A0.15041 (13)1.12177 (10)0.13965 (9)0.0321 (4)
C8A0.15901 (13)1.03289 (10)0.09489 (9)0.0318 (3)
C9A0.33402 (14)0.89556 (11)−0.01453 (9)0.0375 (4)
H9AA0.39680.9341−0.01060.045*
C10A0.34102 (14)0.80607 (11)−0.05895 (9)0.0362 (4)
C11A0.24709 (14)0.75681 (11)−0.08197 (9)0.0378 (4)
H11A0.17710.7822−0.07070.045*
C12A0.25592 (15)0.67071 (12)−0.12138 (10)0.0418 (4)
C13A0.35773 (16)0.63304 (13)−0.13927 (11)0.0483 (5)
H13A0.36350.5745−0.16620.058*
C14A0.45109 (16)0.68217 (14)−0.11715 (12)0.0544 (5)
H14A0.52080.6567−0.12930.065*
C15A0.44415 (15)0.76813 (13)−0.07745 (10)0.0483 (5)
H15A0.50860.8009−0.06290.058*
C16A0.16018 (19)0.54019 (14)−0.18424 (13)0.0643 (6)
H16A0.08550.5176−0.19240.096*
H16B0.20160.4944−0.15220.096*
H16C0.19520.5492−0.23790.096*
C1B−0.03699 (15)0.71162 (12)0.01132 (11)0.0455 (4)
H1BA0.03340.6919−0.00570.055*
C2B−0.12730 (14)0.64846 (11)−0.00231 (10)0.0388 (4)
C3B−0.11454 (17)0.56187 (13)−0.04278 (11)0.0511 (5)
H3BA−0.04450.5427−0.06110.061*
C4B−0.20408 (19)0.50515 (13)−0.05565 (12)0.0596 (5)
H4BA−0.19550.4475−0.08360.072*
C5B−0.30724 (18)0.53223 (13)−0.02775 (12)0.0564 (5)
H5BA−0.36790.4923−0.03640.068*
C6B−0.32239 (15)0.61678 (12)0.01251 (11)0.0447 (4)
H6BA−0.39270.63460.03130.054*
C7B−0.23160 (14)0.67581 (10)0.02510 (9)0.0349 (4)
C8B−0.24254 (14)0.76758 (10)0.06503 (9)0.0324 (3)
C9B−0.42284 (13)0.91673 (11)0.15517 (10)0.0368 (4)
H9BA−0.48810.88700.13780.044*
C10B−0.42954 (13)1.00313 (11)0.20488 (9)0.0353 (4)
C11B−0.33484 (13)1.04619 (10)0.23426 (9)0.0348 (4)
H11B−0.26561.01980.22230.042*
C12B−0.34132 (14)1.12789 (11)0.28118 (9)0.0371 (4)
C13B−0.44355 (15)1.16444 (12)0.30276 (10)0.0440 (4)
H13B−0.44861.21780.33710.053*
C14B−0.53719 (15)1.12146 (12)0.27317 (11)0.0473 (4)
H14B−0.60651.14660.28690.057*
C15B−0.53156 (14)1.04202 (11)0.22357 (10)0.0413 (4)
H15B−0.59641.01450.20270.050*
C16B−0.24432 (17)1.25121 (12)0.35107 (12)0.0554 (5)
H16D−0.16951.27160.36250.083*
H16E−0.28241.23960.40310.083*
H16F−0.28271.29990.32020.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0544 (8)0.0535 (8)0.0702 (9)0.0068 (6)−0.0055 (7)−0.0259 (7)
O1B0.0552 (8)0.0388 (7)0.0444 (7)0.0024 (5)−0.0011 (6)−0.0124 (5)
N1A0.0339 (8)0.0406 (8)0.0568 (9)0.0036 (6)0.0016 (7)−0.0031 (7)
N2A0.0384 (8)0.0336 (7)0.0442 (8)0.0006 (6)−0.0021 (6)−0.0063 (6)
N3A0.0444 (8)0.0318 (7)0.0377 (7)−0.0023 (6)0.0053 (7)−0.0001 (6)
N4A0.0457 (8)0.0304 (7)0.0352 (7)0.0014 (6)0.0018 (7)−0.0002 (6)
N1B0.0406 (8)0.0409 (8)0.0444 (8)0.0013 (6)0.0010 (7)−0.0027 (7)
N2B0.0416 (8)0.0291 (7)0.0384 (7)−0.0002 (6)0.0007 (6)−0.0060 (6)
N3B0.0449 (8)0.0278 (7)0.0397 (7)−0.0052 (6)−0.0018 (7)−0.0052 (6)
N4B0.0420 (8)0.0293 (7)0.0364 (7)−0.0016 (6)0.0020 (6)−0.0021 (6)
C1A0.0375 (10)0.0399 (10)0.0590 (11)0.0028 (7)0.0069 (9)−0.0013 (9)
C2A0.0446 (10)0.0361 (9)0.0358 (8)0.0013 (7)0.0003 (8)0.0011 (7)
C3A0.0577 (12)0.0382 (10)0.0427 (9)0.0060 (8)0.0066 (9)−0.0028 (8)
C4A0.0706 (13)0.0343 (9)0.0395 (9)0.0018 (9)−0.0022 (9)−0.0064 (8)
C5A0.0605 (12)0.0364 (10)0.0468 (10)−0.0089 (8)−0.0087 (9)−0.0029 (8)
C6A0.0433 (10)0.0377 (9)0.0397 (9)−0.0034 (7)−0.0033 (8)0.0006 (7)
C7A0.0381 (9)0.0296 (8)0.0286 (7)−0.0001 (6)−0.0034 (7)0.0025 (6)
C8A0.0379 (9)0.0288 (8)0.0286 (7)0.0004 (6)−0.0043 (7)0.0033 (6)
C9A0.0447 (10)0.0349 (9)0.0330 (8)−0.0030 (7)0.0078 (8)0.0055 (7)
C10A0.0431 (10)0.0369 (9)0.0287 (8)0.0024 (7)0.0046 (7)0.0062 (7)
C11A0.0407 (10)0.0390 (9)0.0336 (8)0.0096 (7)0.0016 (7)−0.0034 (7)
C12A0.0488 (11)0.0432 (10)0.0334 (8)0.0079 (8)−0.0026 (8)−0.0028 (7)
C13A0.0573 (12)0.0465 (10)0.0411 (9)0.0161 (9)0.0011 (9)−0.0050 (8)
C14A0.0453 (11)0.0659 (13)0.0519 (11)0.0192 (10)0.0091 (9)−0.0098 (10)
C15A0.0428 (11)0.0563 (11)0.0460 (10)0.0064 (8)0.0063 (9)0.0006 (9)
C16A0.0768 (15)0.0559 (13)0.0602 (12)0.0015 (10)−0.0052 (12)−0.0202 (10)
C1B0.0467 (11)0.0406 (10)0.0492 (10)0.0066 (8)0.0007 (9)−0.0011 (8)
C2B0.0523 (11)0.0289 (8)0.0351 (8)0.0064 (7)−0.0035 (8)−0.0014 (7)
C3B0.0660 (13)0.0399 (10)0.0474 (10)0.0152 (9)−0.0080 (10)−0.0077 (8)
C4B0.0843 (15)0.0346 (10)0.0599 (12)0.0097 (10)−0.0186 (11)−0.0145 (9)
C5B0.0717 (14)0.0362 (10)0.0611 (12)−0.0089 (9)−0.0153 (11)−0.0062 (9)
C6B0.0523 (11)0.0340 (9)0.0477 (10)−0.0044 (8)−0.0062 (9)−0.0058 (8)
C7B0.0476 (10)0.0285 (8)0.0285 (7)−0.0003 (7)−0.0057 (7)−0.0005 (6)
C8B0.0436 (10)0.0275 (8)0.0261 (7)−0.0018 (7)−0.0038 (7)0.0003 (6)
C9B0.0376 (9)0.0318 (8)0.0411 (9)−0.0063 (7)0.0022 (8)0.0041 (7)
C10B0.0429 (9)0.0297 (8)0.0332 (8)0.0031 (7)0.0087 (7)0.0049 (6)
C11B0.0371 (9)0.0319 (8)0.0355 (8)0.0040 (7)0.0053 (7)−0.0022 (7)
C12B0.0501 (10)0.0306 (8)0.0306 (8)0.0040 (7)0.0019 (8)0.0009 (6)
C13B0.0617 (12)0.0336 (9)0.0367 (9)0.0147 (8)0.0069 (9)−0.0012 (7)
C14B0.0466 (11)0.0460 (10)0.0492 (10)0.0136 (8)0.0087 (9)0.0037 (9)
C15B0.0360 (9)0.0434 (10)0.0446 (9)−0.0003 (7)0.0037 (8)0.0068 (8)
C16B0.0767 (14)0.0413 (10)0.0481 (10)0.0024 (9)−0.0030 (10)−0.0179 (8)
Geometric parameters (Å, °) top
O1A—C12A1.376 (2)C12A—C13A1.377 (2)
O1A—C16A1.428 (2)C13A—C14A1.377 (3)
O1B—C12B1.3740 (19)C13A—H13A0.9400
O1B—C16B1.4248 (19)C14A—C15A1.380 (2)
N1A—C1A1.291 (2)C14A—H14A0.9400
N1A—N2A1.3594 (17)C15A—H15A0.9400
N2A—C8A1.369 (2)C16A—H16A0.9700
N2A—H2AA0.8700C16A—H16B0.9700
N3A—C8A1.3056 (19)C16A—H16C0.9700
N3A—N4A1.3985 (17)C1B—C2B1.433 (2)
N4A—C9A1.2771 (19)C1B—H1BA0.9400
N1B—C1B1.296 (2)C2B—C7B1.395 (2)
N1B—N2B1.3678 (18)C2B—C3B1.400 (2)
N2B—C8B1.3640 (19)C3B—C4B1.368 (3)
N2B—H2BA0.8700C3B—H3BA0.9400
N3B—C8B1.307 (2)C4B—C5B1.384 (3)
N3B—N4B1.3943 (17)C4B—H4BA0.9400
N4B—C9B1.2750 (19)C5B—C6B1.376 (2)
C1A—C2A1.440 (2)C5B—H5BA0.9400
C1A—H1AA0.9400C6B—C7B1.399 (2)
C2A—C7A1.397 (2)C6B—H6BA0.9400
C2A—C3A1.404 (2)C7B—C8B1.459 (2)
C3A—C4A1.364 (3)C9B—C10B1.466 (2)
C3A—H3AA0.9400C9B—H9BA0.9400
C4A—C5A1.383 (3)C10B—C11B1.385 (2)
C4A—H4AA0.9400C10B—C15B1.388 (2)
C5A—C6A1.378 (2)C11B—C12B1.386 (2)
C5A—H5AA0.9400C11B—H11B0.9400
C6A—C7A1.388 (2)C12B—C13B1.389 (2)
C6A—H6AA0.9400C13B—C14B1.375 (2)
C7A—C8A1.457 (2)C13B—H13B0.9400
C9A—C10A1.460 (2)C14B—C15B1.383 (2)
C9A—H9AA0.9400C14B—H14B0.9400
C10A—C11A1.387 (2)C15B—H15B0.9400
C10A—C15A1.395 (2)C16B—H16D0.9700
C11A—C12A1.381 (2)C16B—H16E0.9700
C11A—H11A0.9400C16B—H16F0.9700
C12A—O1A—C16A118.45 (15)C10A—C15A—H15A120.2
C12B—O1B—C16B117.30 (13)O1A—C16A—H16A109.5
C1A—N1A—N2A116.61 (14)O1A—C16A—H16B109.5
N1A—N2A—C8A126.68 (13)H16A—C16A—H16B109.5
N1A—N2A—H2AA116.7O1A—C16A—H16C109.5
C8A—N2A—H2AA116.7H16A—C16A—H16C109.5
C8A—N3A—N4A111.83 (13)H16B—C16A—H16C109.5
C9A—N4A—N3A113.51 (14)N1B—C1B—C2B124.64 (17)
C1B—N1B—N2B116.30 (14)N1B—C1B—H1BA117.7
C8B—N2B—N1B126.61 (13)C2B—C1B—H1BA117.7
C8B—N2B—H2BA116.7C7B—C2B—C3B119.45 (16)
N1B—N2B—H2BA116.7C7B—C2B—C1B118.11 (14)
C8B—N3B—N4B111.63 (13)C3B—C2B—C1B122.43 (17)
C9B—N4B—N3B113.99 (13)C4B—C3B—C2B119.97 (18)
N1A—C1A—C2A124.48 (16)C4B—C3B—H3BA120.0
N1A—C1A—H1AA117.8C2B—C3B—H3BA120.0
C2A—C1A—H1AA117.8C3B—C4B—C5B120.37 (17)
C7A—C2A—C3A119.81 (16)C3B—C4B—H4BA119.8
C7A—C2A—C1A118.05 (15)C5B—C4B—H4BA119.8
C3A—C2A—C1A122.14 (16)C6B—C5B—C4B121.03 (18)
C4A—C3A—C2A119.70 (17)C6B—C5B—H5BA119.5
C4A—C3A—H3AA120.1C4B—C5B—H5BA119.5
C2A—C3A—H3AA120.1C5B—C6B—C7B119.05 (18)
C3A—C4A—C5A120.68 (16)C5B—C6B—H6BA120.5
C3A—C4A—H4AA119.7C7B—C6B—H6BA120.5
C5A—C4A—H4AA119.7C2B—C7B—C6B120.11 (15)
C6A—C5A—C4A120.23 (17)C2B—C7B—C8B118.05 (14)
C6A—C5A—H5AA119.9C6B—C7B—C8B121.82 (16)
C4A—C5A—H5AA119.9N3B—C8B—N2B123.57 (14)
C5A—C6A—C7A120.32 (17)N3B—C8B—C7B120.23 (14)
C5A—C6A—H6AA119.8N2B—C8B—C7B116.20 (14)
C7A—C6A—H6AA119.8N4B—C9B—C10B121.29 (15)
C6A—C7A—C2A119.26 (15)N4B—C9B—H9BA119.4
C6A—C7A—C8A122.82 (15)C10B—C9B—H9BA119.4
C2A—C7A—C8A117.92 (14)C11B—C10B—C15B119.38 (15)
N3A—C8A—N2A123.68 (14)C11B—C10B—C9B120.61 (14)
N3A—C8A—C7A120.08 (14)C15B—C10B—C9B120.01 (15)
N2A—C8A—C7A116.23 (14)C10B—C11B—C12B120.53 (15)
N4A—C9A—C10A120.94 (15)C10B—C11B—H11B119.7
N4A—C9A—H9AA119.5C12B—C11B—H11B119.7
C10A—C9A—H9AA119.5O1B—C12B—C11B115.26 (14)
C11A—C10A—C15A119.05 (15)O1B—C12B—C13B124.77 (15)
C11A—C10A—C9A121.42 (15)C11B—C12B—C13B119.96 (16)
C15A—C10A—C9A119.52 (16)C14B—C13B—C12B119.09 (16)
C12A—C11A—C10A120.31 (16)C14B—C13B—H13B120.5
C12A—C11A—H11A119.8C12B—C13B—H13B120.5
C10A—C11A—H11A119.8C13B—C14B—C15B121.37 (16)
O1A—C12A—C13A124.04 (16)C13B—C14B—H14B119.3
O1A—C12A—C11A115.33 (15)C15B—C14B—H14B119.3
C13A—C12A—C11A120.63 (17)C14B—C15B—C10B119.56 (16)
C12A—C13A—C14A119.18 (17)C14B—C15B—H15B120.2
C12A—C13A—H13A120.4C10B—C15B—H15B120.2
C14A—C13A—H13A120.4O1B—C16B—H16D109.5
C13A—C14A—C15A121.15 (17)O1B—C16B—H16E109.5
C13A—C14A—H14A119.4H16D—C16B—H16E109.5
C15A—C14A—H14A119.4O1B—C16B—H16F109.5
C14A—C15A—C10A119.68 (18)H16D—C16B—H16F109.5
C14A—C15A—H15A120.2H16E—C16B—H16F109.5
C1A—N1A—N2A—C8A−1.0 (2)C11A—C10A—C15A—C14A−0.8 (2)
C8A—N3A—N4A—C9A−178.96 (13)C9A—C10A—C15A—C14A178.01 (15)
C1B—N1B—N2B—C8B2.6 (2)N2B—N1B—C1B—C2B0.5 (2)
C8B—N3B—N4B—C9B172.58 (13)N1B—C1B—C2B—C7B−2.0 (3)
N2A—N1A—C1A—C2A0.1 (3)N1B—C1B—C2B—C3B177.08 (15)
N1A—C1A—C2A—C7A0.1 (3)C7B—C2B—C3B—C4B0.4 (3)
N1A—C1A—C2A—C3A−179.98 (16)C1B—C2B—C3B—C4B−178.65 (17)
C7A—C2A—C3A—C4A−0.2 (2)C2B—C3B—C4B—C5B−1.0 (3)
C1A—C2A—C3A—C4A179.81 (16)C3B—C4B—C5B—C6B0.7 (3)
C2A—C3A—C4A—C5A0.0 (3)C4B—C5B—C6B—C7B0.0 (3)
C3A—C4A—C5A—C6A0.2 (3)C3B—C2B—C7B—C6B0.3 (2)
C4A—C5A—C6A—C7A−0.3 (2)C1B—C2B—C7B—C6B179.45 (15)
C5A—C6A—C7A—C2A0.1 (2)C3B—C2B—C7B—C8B−178.37 (13)
C5A—C6A—C7A—C8A179.61 (14)C1B—C2B—C7B—C8B0.7 (2)
C3A—C2A—C7A—C6A0.2 (2)C5B—C6B—C7B—C2B−0.6 (2)
C1A—C2A—C7A—C6A−179.89 (15)C5B—C6B—C7B—C8B178.09 (14)
C3A—C2A—C7A—C8A−179.37 (14)N4B—N3B—C8B—N2B−6.1 (2)
C1A—C2A—C7A—C8A0.6 (2)N4B—N3B—C8B—C7B174.81 (12)
N4A—N3A—C8A—N2A1.8 (2)N1B—N2B—C8B—N3B177.24 (14)
N4A—N3A—C8A—C7A−178.92 (12)N1B—N2B—C8B—C7B−3.7 (2)
N1A—N2A—C8A—N3A−179.13 (14)C2B—C7B—C8B—N3B−179.08 (14)
N1A—N2A—C8A—C7A1.6 (2)C6B—C7B—C8B—N3B2.2 (2)
C6A—C7A—C8A—N3A−0.1 (2)C2B—C7B—C8B—N2B1.8 (2)
C2A—C7A—C8A—N3A179.37 (13)C6B—C7B—C8B—N2B−176.90 (14)
C6A—C7A—C8A—N2A179.17 (14)N3B—N4B—C9B—C10B175.84 (12)
C2A—C7A—C8A—N2A−1.3 (2)N4B—C9B—C10B—C11B−2.7 (2)
N3A—N4A—C9A—C10A178.92 (12)N4B—C9B—C10B—C15B177.89 (14)
N4A—C9A—C10A—C11A14.1 (2)C15B—C10B—C11B—C12B−0.7 (2)
N4A—C9A—C10A—C15A−164.71 (15)C9B—C10B—C11B—C12B179.95 (13)
C15A—C10A—C11A—C12A1.1 (2)C16B—O1B—C12B—C11B179.70 (14)
C9A—C10A—C11A—C12A−177.74 (13)C16B—O1B—C12B—C13B−0.4 (2)
C16A—O1A—C12A—C13A−2.5 (3)C10B—C11B—C12B—O1B−176.73 (13)
C16A—O1A—C12A—C11A177.52 (15)C10B—C11B—C12B—C13B3.4 (2)
C10A—C11A—C12A—O1A179.25 (14)O1B—C12B—C13B—C14B176.61 (14)
C10A—C11A—C12A—C13A−0.8 (2)C11B—C12B—C13B—C14B−3.5 (2)
O1A—C12A—C13A—C14A−179.82 (16)C12B—C13B—C14B—C15B1.0 (3)
C11A—C12A—C13A—C14A0.2 (3)C13B—C14B—C15B—C10B1.7 (2)
C12A—C13A—C14A—C15A0.1 (3)C11B—C10B—C15B—C14B−1.9 (2)
C13A—C14A—C15A—C10A0.3 (3)C9B—C10B—C15B—C14B177.52 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···N1B0.872.363.0451 (19)136
N2B—H2BA···N1A0.872.363.0466 (19)136
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···N1B0.872.363.0451 (19)136
N2B—H2BA···N1A0.872.363.0466 (19)136
Acknowledgements top

AMV thanks SeQuent Scientific Ltd, Mangalore, India, for the sample of the starting material, 1-hydrazinophthalazine. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

references
References top

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