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In the crystal lattice of the title compound, 1,5-di­phenyl­carbonohydrazide aceto­nitrile solvate, C13H14N4O·C2H3N, the di­phenyl­carbazide mol­ecules create a network structure through hydrogen bonds. The crystal structure is stabilized by N—H...N and N—H...O hydrogen bonds. The FT–IR spectra clearly show the presence of aceto­nitrile mol­ecules in the crystal lattice.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100397X/na6060sup1.cif
Contains datablocks global, jff62m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100397X/na6060Isup2.hkl
Contains datablock I

CCDC reference: 162812

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.171
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry
Yellow Alert Alert Level C:
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5886 PLAT_321 Alert C Check Hybridisation of C(14) in solvent/ion ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Diphenylcarbazide is an artificial electron-donor material frequently used in analytical chemistry for calorimetric determination of chromium and as a sensitive reagent for metal ions (mercury and cadmium) (El-Kabbany et al., 1997). It has various applications, specially in the field of biophysics and microbiology. With the help of exogenous electron donors, diphenylcarbazide photo-inactivated sites on the electron-transfer chain were delineated (Verma & Singh, 1995). It is also used as an artificial donor during charge separation in photochemical reactions (Melis et al., 1992) and also in photosynthetic electron transport (Prasad et al., 1991; Sundari & Raghavendra, 1990; Mishra et al., 1993). The crystal structure for diphenylcarbazide (C13H14N4O) was determined (De Ranter et al., 1979), which was found to be orthorhombic with space group Pbnm. In this paper, we report the c rystal structure of diphenylcarbazide acetonitrile solvate, (I).

A displacement ellipsoid plot with the atom-numbering scheme is shown in Fig. 1. The bonds and angles observed in this structure are normal and in agreement with those of related structures reported earlier (De Ranter et al., 1979; Burke-Laing & Laing, 1976; Blaton et al., 1979). The C15N5 triple bond is in quite good agreement with the average values of 1.136 (10) Å given by Allen et al. (1987). The torsion angles defining the conformation of the central part of the host molecule are 68.3 (3) and 93.3 (2)°, respectively, for C6—N1—N2—C7 and C7—N3—N4—C8. The dihedral angle between the two planes of the phenyl rings is 52.3 (1)°; these two rings make angles of 79.5 (1) and 85.4 (1)° with the central ureylene moiety (N2/C7/O1/N3). It is also noted that not only the central ureylene moiety is planar, but N1 and N4 lie in its plane. The acetonitrile molecule also lies almost in the plane of the central ureylene group with a dihedral angle of 14.9 (2)°.

In the crystal lattice, the molecules create a network structure through hydrogen bonds. There are four intermolecular hydrogen bonds which form the hydrogen-bond network. The acetonitrile molecule acts as an acceptor connecting two diphenylcarbazide molecules. The O atom of ureylene group is involved in two O···H—N hydrogen bonds with neighboring molecules. Finally, there is an intramolecular N2—H2A···N4 hydrogen bond.

Comparing the structure of (I) with the crystal structure of diphenylcarbazide reported by De Ranter et al. (1979), some differences were noted. Firstly, the phenylidrazine groups are not crystallographically equivalent to each other; secondly, there are no hexagonal units linked into a herring-bone structure; thirdly, there is no marked bond delocalization in the hydrazo chain (C6—N1—N2—C7 and C7—N3—N4—C8), for C6—N1 and C8—N4 are indicative of considerable partly single-bond character. Because of the effect of acetonitrile molecule, the N1—N2, N1—C6 and N2—C7 bond lengths are shorter than those of N3—N4, N4—C8 and N3—C7, respectively. The FT–IR spectra clearly show a strong peak at 2251 cm-1, which was tentatively assigned as the ν(CN) stretching vibration of the acetonitrile molecules in the crystal lattice.

Experimental top

The title compound was prepared by refluxing an acetonitrile solution of diphenylcarbazide (0.484 g, 2 mmol) and PdCl2 (0.1 mg). The deep-red solution was filtered and the filtrate was left to stand undisturbed. Single crystals suitable for X-ray analysis were obtained by slow evaporation at 338–340 K from the acetonitrile solvent.

Structure description top

Diphenylcarbazide is an artificial electron-donor material frequently used in analytical chemistry for calorimetric determination of chromium and as a sensitive reagent for metal ions (mercury and cadmium) (El-Kabbany et al., 1997). It has various applications, specially in the field of biophysics and microbiology. With the help of exogenous electron donors, diphenylcarbazide photo-inactivated sites on the electron-transfer chain were delineated (Verma & Singh, 1995). It is also used as an artificial donor during charge separation in photochemical reactions (Melis et al., 1992) and also in photosynthetic electron transport (Prasad et al., 1991; Sundari & Raghavendra, 1990; Mishra et al., 1993). The crystal structure for diphenylcarbazide (C13H14N4O) was determined (De Ranter et al., 1979), which was found to be orthorhombic with space group Pbnm. In this paper, we report the c rystal structure of diphenylcarbazide acetonitrile solvate, (I).

A displacement ellipsoid plot with the atom-numbering scheme is shown in Fig. 1. The bonds and angles observed in this structure are normal and in agreement with those of related structures reported earlier (De Ranter et al., 1979; Burke-Laing & Laing, 1976; Blaton et al., 1979). The C15N5 triple bond is in quite good agreement with the average values of 1.136 (10) Å given by Allen et al. (1987). The torsion angles defining the conformation of the central part of the host molecule are 68.3 (3) and 93.3 (2)°, respectively, for C6—N1—N2—C7 and C7—N3—N4—C8. The dihedral angle between the two planes of the phenyl rings is 52.3 (1)°; these two rings make angles of 79.5 (1) and 85.4 (1)° with the central ureylene moiety (N2/C7/O1/N3). It is also noted that not only the central ureylene moiety is planar, but N1 and N4 lie in its plane. The acetonitrile molecule also lies almost in the plane of the central ureylene group with a dihedral angle of 14.9 (2)°.

In the crystal lattice, the molecules create a network structure through hydrogen bonds. There are four intermolecular hydrogen bonds which form the hydrogen-bond network. The acetonitrile molecule acts as an acceptor connecting two diphenylcarbazide molecules. The O atom of ureylene group is involved in two O···H—N hydrogen bonds with neighboring molecules. Finally, there is an intramolecular N2—H2A···N4 hydrogen bond.

Comparing the structure of (I) with the crystal structure of diphenylcarbazide reported by De Ranter et al. (1979), some differences were noted. Firstly, the phenylidrazine groups are not crystallographically equivalent to each other; secondly, there are no hexagonal units linked into a herring-bone structure; thirdly, there is no marked bond delocalization in the hydrazo chain (C6—N1—N2—C7 and C7—N3—N4—C8), for C6—N1 and C8—N4 are indicative of considerable partly single-bond character. Because of the effect of acetonitrile molecule, the N1—N2, N1—C6 and N2—C7 bond lengths are shorter than those of N3—N4, N4—C8 and N3—C7, respectively. The FT–IR spectra clearly show a strong peak at 2251 cm-1, which was tentatively assigned as the ν(CN) stretching vibration of the acetonitrile molecules in the crystal lattice.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); 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, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
(jff62m) top
Crystal data top
C15H17N5OF(000) = 600
Mr = 283.34Dx = 1.227 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.7818 (2) ÅCell parameters from 4025 reflections
b = 15.320 (1) Åθ = 1.8–24.8°
c = 17.469 (1) ŵ = 0.08 mm1
β = 97.476 (1)°T = 293 K
V = 1534.20 (14) Å3Parallelepiped, light yellow
Z = 40.48 × 0.34 × 0.18 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1756 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 24.7°, θmin = 1.8°
Detector resolution: 8.33 pixels mm-1h = 66
ω scansk = 1817
8214 measured reflectionsl = 1420
2624 independent reflections
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.1025P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2624 reflectionsΔρmax = 0.37 e Å3
191 parametersΔρmin = 0.47 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (5)
Crystal data top
C15H17N5OV = 1534.20 (14) Å3
Mr = 283.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.7818 (2) ŵ = 0.08 mm1
b = 15.320 (1) ÅT = 293 K
c = 17.469 (1) Å0.48 × 0.34 × 0.18 mm
β = 97.476 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
1756 reflections with I > 2σ(I)
8214 measured reflectionsRint = 0.056
2624 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.01Δρmax = 0.37 e Å3
2624 reflectionsΔρmin = 0.47 e Å3
191 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99.7% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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
xyzUiso*/Ueq
O10.2298 (2)0.02618 (10)0.08467 (9)0.0500 (5)
N10.2917 (3)0.12213 (13)0.21908 (12)0.0574 (6)
H1A0.38510.16610.22250.069*
N20.0912 (3)0.12298 (13)0.16609 (11)0.0491 (5)
H2A0.01970.15850.17260.059*
N30.1502 (3)0.06424 (12)0.06440 (11)0.0442 (5)
H3A0.18340.02390.03050.053*
N40.3182 (3)0.12511 (11)0.07862 (10)0.0421 (5)
H4A0.40450.11750.11460.050*
N50.7416 (6)0.24647 (18)0.24697 (19)0.1068 (11)
C10.1821 (4)0.01479 (18)0.27475 (15)0.0599 (7)
H1B0.03400.01180.24680.072*
C20.2397 (5)0.0841 (2)0.32369 (18)0.0756 (9)
H2B0.13080.12810.32740.091*
C30.4544 (5)0.08960 (19)0.36697 (17)0.0728 (8)
H3B0.49200.13660.39990.087*
C40.6124 (5)0.02428 (19)0.36066 (16)0.0657 (8)
H4B0.75820.02680.39010.079*
C50.5589 (4)0.04477 (16)0.31158 (14)0.0514 (6)
H5A0.66860.08850.30810.062*
C60.3414 (4)0.04983 (14)0.26685 (12)0.0416 (6)
C70.0673 (4)0.06916 (14)0.10475 (12)0.0385 (5)
C80.3399 (3)0.20007 (14)0.03097 (11)0.0391 (5)
C90.1753 (4)0.22137 (17)0.01703 (14)0.0532 (7)
H9A0.04710.18530.01950.064*
C100.2024 (5)0.29622 (19)0.06116 (16)0.0662 (8)
H10A0.09270.30970.09380.079*
C110.3872 (5)0.35074 (19)0.05764 (18)0.0706 (8)
H11A0.40280.40130.08730.085*
C120.5504 (5)0.33034 (18)0.00980 (16)0.0650 (8)
H12A0.67690.36720.00710.078*
C130.5271 (4)0.25551 (15)0.03406 (14)0.0507 (6)
H13A0.63850.24210.06610.061*
C140.8849 (7)0.3712 (2)0.3392 (2)0.0976 (12)
C150.8028 (5)0.30067 (19)0.28802 (18)0.0688 (8)
H14C0.75960.36500.35820.103*
H14B0.96990.34340.38070.103*
H14A0.86110.42150.31810.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0355 (8)0.0568 (10)0.0584 (10)0.0079 (7)0.0087 (7)0.0018 (8)
N10.0483 (12)0.0628 (13)0.0554 (13)0.0102 (10)0.0148 (10)0.0093 (11)
N20.0417 (10)0.0600 (12)0.0431 (11)0.0072 (9)0.0040 (9)0.0041 (10)
N30.0365 (10)0.0488 (11)0.0470 (11)0.0053 (8)0.0044 (8)0.0071 (9)
N40.0358 (10)0.0531 (11)0.0395 (10)0.0084 (8)0.0132 (8)0.0030 (9)
N50.147 (3)0.0764 (19)0.094 (2)0.0329 (19)0.003 (2)0.0033 (17)
C10.0474 (14)0.0786 (18)0.0520 (15)0.0143 (13)0.0000 (12)0.0077 (14)
C20.0773 (19)0.079 (2)0.0707 (19)0.0228 (16)0.0094 (16)0.0175 (16)
C30.0757 (19)0.0739 (18)0.0676 (19)0.0014 (16)0.0039 (16)0.0222 (16)
C40.0551 (15)0.0778 (19)0.0602 (16)0.0099 (15)0.0074 (13)0.0051 (15)
C50.0439 (13)0.0573 (14)0.0509 (14)0.0016 (11)0.0014 (11)0.0026 (12)
C60.0396 (12)0.0517 (13)0.0340 (11)0.0021 (10)0.0067 (9)0.0042 (10)
C70.0351 (11)0.0429 (12)0.0375 (12)0.0000 (10)0.0052 (9)0.0048 (10)
C80.0349 (11)0.0491 (13)0.0324 (11)0.0015 (9)0.0009 (9)0.0047 (10)
C90.0407 (13)0.0686 (16)0.0520 (14)0.0002 (11)0.0125 (11)0.0070 (13)
C100.0576 (16)0.083 (2)0.0602 (16)0.0051 (15)0.0162 (13)0.0176 (15)
C110.0732 (18)0.0668 (18)0.0704 (19)0.0012 (15)0.0037 (16)0.0228 (15)
C120.0631 (17)0.0668 (17)0.0644 (17)0.0205 (14)0.0063 (14)0.0090 (15)
C130.0450 (13)0.0586 (15)0.0504 (14)0.0069 (11)0.0130 (11)0.0023 (12)
C140.140 (3)0.0703 (19)0.070 (2)0.0028 (19)0.031 (2)0.0063 (17)
C150.084 (2)0.0560 (16)0.0625 (17)0.0127 (15)0.0043 (15)0.0083 (15)
Geometric parameters (Å, º) top
O1—C71.235 (2)C4—C51.371 (3)
N1—N21.386 (3)C4—H4B0.9300
N1—C61.394 (3)C5—C61.393 (3)
N1—H1A0.8600C5—H5A0.9300
N2—C71.345 (3)C8—C131.383 (3)
N2—H2A0.8600C8—C91.387 (3)
N3—C71.361 (3)C9—C101.379 (4)
N3—N41.392 (2)C9—H9A0.9300
N3—H3A0.8600C10—C111.364 (4)
N4—C81.414 (3)C10—H10A0.9300
N4—H4A0.8600C11—C121.375 (4)
N5—C151.124 (4)C11—H11A0.9300
C1—C61.372 (3)C12—C131.376 (3)
C1—C21.377 (4)C12—H12A0.9300
C1—H1B0.9300C13—H13A0.9300
C2—C31.369 (4)C14—C151.442 (5)
C2—H2B0.9300C14—H14C0.8411
C3—C41.369 (4)C14—H14B0.9258
C3—H3B0.9300C14—H14A0.8575
N2—N1—C6119.8 (2)C5—C6—N1118.7 (2)
N2—N1—H1A120.1O1—C7—N2123.36 (19)
C6—N1—H1A120.1O1—C7—N3120.6 (2)
C7—N2—N1121.1 (2)N2—C7—N3116.03 (19)
C7—N2—H2A119.4C13—C8—C9118.8 (2)
N1—N2—H2A119.4C13—C8—N4119.08 (19)
C7—N3—N4119.3 (2)C9—C8—N4122.1 (2)
C7—N3—H3A120.3C10—C9—C8119.8 (2)
N4—N3—H3A120.3C10—C9—H9A120.1
N3—N4—C8116.72 (16)C8—C9—H9A120.1
N3—N4—H4A121.6C11—C10—C9121.1 (2)
C8—N4—H4A121.6C11—C10—H10A119.5
C6—C1—C2120.5 (2)C9—C10—H10A119.5
C6—C1—H1B119.7C10—C11—C12119.5 (3)
C2—C1—H1B119.7C10—C11—H11A120.3
C3—C2—C1121.3 (3)C12—C11—H11A120.3
C3—C2—H2B119.4C11—C12—C13120.2 (2)
C1—C2—H2B119.4C11—C12—H12A119.9
C4—C3—C2118.5 (3)C13—C12—H12A119.9
C4—C3—H3B120.8C12—C13—C8120.7 (2)
C2—C3—H3B120.8C12—C13—H13A119.6
C3—C4—C5121.0 (2)C8—C13—H13A119.6
C3—C4—H4B119.5C15—C14—H14C86.0
C5—C4—H4B119.5C15—C14—H14B103.9
C4—C5—C6120.5 (2)H14C—C14—H14B92.0
C4—C5—H5A119.8C15—C14—H14A112.8
C6—C5—H5A119.8H14C—C14—H14A99.9
C1—C6—C5118.2 (2)H14B—C14—H14A142.0
C1—C6—N1123.0 (2)N5—C15—C14178.5 (4)
C6—N1—N2—C768.3 (3)N1—N2—C7—N3168.7 (2)
C7—N3—N4—C893.3 (2)N4—N3—C7—O1167.60 (18)
C6—C1—C2—C31.5 (5)N4—N3—C7—N212.2 (3)
C1—C2—C3—C40.0 (5)N3—N4—C8—C13169.73 (19)
C2—C3—C4—C50.7 (5)N3—N4—C8—C912.4 (3)
C3—C4—C5—C60.0 (4)C13—C8—C9—C100.8 (4)
C2—C1—C6—C52.2 (4)N4—C8—C9—C10178.7 (2)
C2—C1—C6—N1179.0 (2)C8—C9—C10—C111.0 (4)
C4—C5—C6—C11.5 (3)C9—C10—C11—C120.6 (4)
C4—C5—C6—N1178.4 (2)C10—C11—C12—C130.0 (4)
N2—N1—C6—C112.4 (3)C11—C12—C13—C80.2 (4)
N2—N1—C6—C5170.8 (2)C9—C8—C13—C120.2 (3)
N1—N2—C7—O111.6 (3)N4—C8—C13—C12178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N50.862.393.210 (4)159
N2—H2A···N5i0.862.423.226 (4)155
N3—H3A···O1ii0.862.142.933 (2)154
N4—H4A···O1i0.862.533.035 (2)118
N2—H2A···N40.862.282.645 (3)106
Symmetry codes: (i) x1, y, z; (ii) x, y, z.

Experimental details

Crystal data
Chemical formulaC15H17N5O
Mr283.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)5.7818 (2), 15.320 (1), 17.469 (1)
β (°) 97.476 (1)
V3)1534.20 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.48 × 0.34 × 0.18
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8214, 2624, 1756
Rint0.056
(sin θ/λ)max1)0.589
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.171, 1.01
No. of reflections2624
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.47

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O1—C71.235 (2)N3—C71.361 (3)
N1—N21.386 (3)N3—N41.392 (2)
N1—C61.394 (3)N4—C81.414 (3)
N2—C71.345 (3)N5—C151.124 (4)
N2—N1—C6119.8 (2)C7—N3—N4119.3 (2)
C7—N2—N1121.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N50.862.393.210 (4)159
N2—H2A···N5i0.862.423.226 (4)155
N3—H3A···O1ii0.862.142.933 (2)154
N4—H4A···O1i0.862.533.035 (2)118
N2—H2A···N40.862.282.645 (3)106
Symmetry codes: (i) x1, y, z; (ii) x, y, z.
 

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