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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1961–o1962.
Published online 2008 September 20. doi:  10.1107/S1600536808029218
PMCID: PMC2959329

N′-[(E)-1-Phenyl­ethyl­idene]benzo­hydrazide

Abstract

The title compound, C15H14N2O, crystallized with two independent mol­ecules in the asymmetric unit. Both mol­ecules are non-planar and have an E configuration with respect to the C=N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in one mol­ecule and 12.40 (19)° in the other. In the crystal structure, the mol­ecules are linked by N—H(...)O hydrogen bonds and weak C—H(...)O inter­actions into infinite one-dimensional chains along [1 0 0]. The crystal structure is further stabilized by N—H(...)O hydrogen bonds, weak C—H(...)O and very weak C—H(...)π inter­actions.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For background to the applications of hydrazone and benzohydrazide, see, for example: Bratenko et al. (1999 [triangle]); Raj et al. (2007 [triangle]); Rollas et al. (2002 [triangle]); Sridhar et al. (2003 [triangle]); Zhang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1961-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O
  • M r = 238.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1961-efi1.jpg
  • a = 8.2237 (6) Å
  • b = 5.5938 (4) Å
  • c = 52.839 (4) Å
  • V = 2430.7 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100.0 (1) K
  • 0.50 × 0.22 × 0.05 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.959, T max = 0.996
  • 23699 measured reflections
  • 3572 independent reflections
  • 2925 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.159
  • S = 1.08
  • 3572 reflections
  • 327 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029218/si2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029218/si2108Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Hydrazones are versatile intermediates and important building blocks. Hydrazones of aliphatic and aromatic methyl ketones yield pyrazole-4-carboxaldehyde upon diformylation on treatment with Vilsmeier reagent (Bratenko et al., 1999). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar et al., 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Rollas et al., 2002). Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as well as their metal complexes as target structures and evaluated their biological activities (Raj et al., 2007; Zhang et al., 2007). These observations guided us to synthesize the title compound and its crystal structure was reported here.

In the asymmetric unit of the title compound (Fig. 1), there are two independent molecules A and B. Bond lengths in molecules A and B are slightly different but all are in normal ranges (Allen et al., 1987). Both molecules are not planar and exist in the E configuration which respect to the C═N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in A and 12.40 (19)° in B. In molecule A, the interplanar angle between the mean plane through N2A/O2A/C8A/C9A and N1A/N2A/C6A/C7A/C15A planes = 20.8 (2)°. In molecule B atoms N1B, N2B, C7B and C15B lie on the same plane and this plane makes the dihedral angle with the mean plane through N2B/O2B/C8B/C9B = 20.4 (2)°.

Fig. 2 shows that the molecules are linked into chains along [1 0 0] through N—H···O hydrogen bonds and weak C—H···O and very weak C—H···π interactions (Table 1); Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1A–C6A, C1B–C6B, C9A–C14A and C9B–C14B rings, respectively.

Experimental

The title compound was obtained by refluxing phenyl hydrazide (0.01 mol) and acetophenone (0.01 mol) in ethanol (30 ml) by adding 3 drops of concentrated Sulfuric acid for 3 hr. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were grown by slow evaporation of an ethanol solution at room temperature.

Refinement

All H atoms were constrained in a riding motion approximation with N—H = 0.73 and 0.91 Å, Caryl—H=0.93 and Cmethyl—H=0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.76 Å from C10A and the deepest hole is located at 0.72 Å from H1AA. As there is no large anomalous dispersion for the determination of the absolute structure, a total of 2250 Friedel pairs were merged before final refinement.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of the major components of (I), viewed along the b axis showing that the molecules are linked in infinite one-dimensional chains along the a axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C15H14N2OF(000) = 1008
Mr = 238.28Dx = 1.302 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3572 reflections
a = 8.2237 (6) Åθ = 0.8–30.0°
b = 5.5938 (4) ŵ = 0.08 mm1
c = 52.839 (4) ÅT = 100 K
V = 2430.7 (3) Å3Plate, colorless
Z = 80.50 × 0.22 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer3572 independent reflections
Radiation source: fine-focus sealed tube2925 reflections with I > 2σ(I)
graphiteRint = 0.069
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 0.8°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −7→7
Tmin = 0.959, Tmax = 0.996l = −74→73
23699 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0598P)2 + 2.0097P] where P = (Fo2 + 2Fc2)/3
3572 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.29 e Å3
1 restraintΔρmin = −0.30 e Å3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)

xyzUiso*/Ueq
O2A0.4444 (3)−0.2422 (5)0.28192 (5)0.0225 (5)
N1A0.5650 (4)0.0608 (6)0.24842 (6)0.0211 (7)
N2A0.6306 (4)0.0417 (6)0.27253 (6)0.0201 (7)
H2NA0.73580.09120.27460.024*
C1A0.5851 (5)0.4279 (7)0.19173 (7)0.0228 (8)
H1AA0.65610.54810.19680.027*
C2A0.5277 (5)0.4246 (7)0.16709 (7)0.0248 (8)
H2AA0.56040.54250.15580.030*
C3A0.4219 (5)0.2471 (7)0.15916 (7)0.0237 (8)
H3AA0.38460.24450.14260.028*
C4A0.3719 (6)0.0726 (7)0.17624 (8)0.0259 (8)
H4AA0.2996−0.04570.17110.031*
C5A0.4294 (5)0.0744 (7)0.20083 (7)0.0221 (8)
H5AA0.3959−0.04400.21200.026*
C6A0.5372 (5)0.2515 (6)0.20916 (7)0.0183 (7)
C7A0.6028 (4)0.2496 (6)0.23548 (7)0.0186 (7)
C8A0.5670 (5)−0.1290 (6)0.28767 (7)0.0194 (7)
C9A0.6454 (5)−0.1709 (6)0.31291 (7)0.0192 (7)
C10A0.6062 (5)−0.3840 (7)0.32523 (7)0.0237 (8)
H10A0.5381−0.49420.31740.028*
C11A0.6686 (6)−0.4318 (7)0.34912 (8)0.0281 (9)
H11A0.6405−0.57270.35740.034*
C12A0.7725 (5)−0.2705 (7)0.36069 (8)0.0284 (9)
H12A0.8161−0.30450.37650.034*
C13A0.8115 (5)−0.0584 (7)0.34857 (7)0.0264 (8)
H13A0.87980.05090.35650.032*
C14A0.7494 (5)−0.0079 (7)0.32479 (7)0.0223 (7)
H14A0.77680.13430.31670.027*
C15A0.7015 (5)0.4561 (6)0.24455 (8)0.0240 (8)
H15A0.69780.46270.26270.036*
H15B0.65810.60160.23770.036*
H15C0.81210.43700.23910.036*
O2B0.7470 (3)0.7474 (4)0.48915 (5)0.0219 (5)
N1B0.8664 (4)0.4422 (5)0.52262 (6)0.0191 (6)
N2B0.9356 (4)0.4640 (6)0.49876 (6)0.0217 (7)
H2NB1.00560.40270.49340.026*
C1B0.8836 (5)0.0735 (7)0.57897 (7)0.0230 (8)
H1BA0.9549−0.04590.57380.028*
C2B0.8256 (5)0.0752 (7)0.60357 (7)0.0256 (8)
H2BA0.8590−0.04190.61490.031*
C3B0.7171 (5)0.2523 (7)0.61138 (7)0.0242 (8)
H3BA0.67780.25290.62790.029*
C4B0.6682 (5)0.4275 (7)0.59443 (7)0.0233 (8)
H4BA0.59530.54500.59960.028*
C5B0.7273 (5)0.4279 (6)0.56996 (7)0.0214 (8)
H5BA0.69500.54720.55880.026*
C6B0.8357 (5)0.2499 (6)0.56181 (7)0.0178 (7)
C7B0.9020 (5)0.2528 (6)0.53547 (7)0.0181 (7)
C8B0.8716 (5)0.6352 (6)0.48358 (7)0.0191 (7)
C9B0.9556 (5)0.6867 (7)0.45879 (7)0.0200 (7)
C10B0.9161 (5)0.9028 (7)0.44669 (8)0.0239 (8)
H10B0.84491.00980.45430.029*
C11B0.9835 (5)0.9560 (7)0.42336 (7)0.0248 (8)
H11B0.95751.09900.41530.030*
C12B1.0899 (5)0.7967 (7)0.41187 (7)0.0258 (8)
H12B1.13450.83330.39620.031*
C13B1.1300 (5)0.5833 (7)0.42368 (7)0.0249 (8)
H13B1.20330.47850.41610.030*
C14B1.0592 (5)0.5268 (7)0.44704 (7)0.0228 (8)
H14B1.08210.38090.45470.027*
C15B1.0038 (5)0.0472 (6)0.52656 (7)0.0215 (8)
H15D1.01350.05310.50850.032*
H15E0.9531−0.10040.53140.032*
H15F1.10990.05710.53410.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O2A0.0164 (13)0.0242 (12)0.0268 (13)−0.0029 (11)−0.0018 (11)0.0001 (10)
N1A0.0199 (17)0.0221 (15)0.0214 (15)−0.0012 (12)−0.0012 (13)0.0022 (12)
N2A0.0191 (17)0.0198 (15)0.0213 (16)−0.0015 (12)−0.0014 (13)0.0019 (12)
C1A0.023 (2)0.0184 (16)0.027 (2)−0.0005 (14)0.0004 (15)0.0014 (14)
C2A0.023 (2)0.0258 (18)0.0253 (19)0.0017 (16)−0.0004 (16)0.0067 (15)
C3A0.025 (2)0.0271 (19)0.0189 (17)0.0047 (16)−0.0020 (15)0.0016 (14)
C4A0.029 (2)0.0225 (18)0.0258 (18)−0.0018 (16)−0.0003 (16)−0.0034 (15)
C5A0.0199 (19)0.0209 (17)0.0254 (18)−0.0009 (15)0.0002 (15)0.0020 (14)
C6A0.0164 (17)0.0182 (15)0.0203 (16)0.0023 (13)0.0006 (13)0.0000 (13)
C7A0.0143 (17)0.0199 (16)0.0216 (17)0.0029 (13)−0.0002 (13)−0.0012 (13)
C8A0.0195 (18)0.0158 (15)0.0229 (18)0.0009 (14)0.0000 (15)0.0001 (13)
C9A0.0168 (18)0.0188 (16)0.0221 (17)0.0005 (13)0.0011 (14)0.0027 (13)
C10A0.025 (2)0.0204 (17)0.0261 (19)0.0000 (15)−0.0029 (16)0.0017 (14)
C11A0.028 (2)0.0273 (19)0.029 (2)0.0009 (16)0.0015 (17)0.0061 (16)
C12A0.028 (2)0.034 (2)0.0226 (18)0.0027 (17)−0.0020 (16)0.0043 (16)
C13A0.021 (2)0.033 (2)0.0253 (19)−0.0016 (16)0.0004 (16)−0.0012 (15)
C14A0.022 (2)0.0233 (16)0.0218 (18)−0.0040 (16)0.0001 (16)0.0010 (14)
C15A0.024 (2)0.0192 (17)0.029 (2)0.0007 (15)−0.0032 (16)−0.0005 (14)
O2B0.0192 (13)0.0213 (12)0.0253 (13)0.0023 (11)0.0021 (10)0.0007 (10)
N1B0.0182 (16)0.0200 (14)0.0193 (15)−0.0017 (12)0.0029 (12)−0.0006 (11)
N2B0.0213 (17)0.0247 (15)0.0190 (15)0.0021 (13)0.0058 (13)−0.0008 (12)
C1B0.0215 (19)0.0189 (16)0.028 (2)0.0017 (14)0.0004 (16)0.0025 (15)
C2B0.025 (2)0.0252 (18)0.027 (2)0.0000 (16)−0.0021 (17)0.0070 (15)
C3B0.022 (2)0.0281 (18)0.0221 (18)−0.0019 (15)0.0016 (15)0.0002 (15)
C4B0.024 (2)0.0255 (18)0.0210 (17)0.0030 (16)0.0015 (15)−0.0030 (14)
C5B0.026 (2)0.0183 (15)0.0205 (17)0.0028 (14)−0.0004 (15)0.0012 (13)
C6B0.0158 (17)0.0142 (14)0.0235 (16)−0.0021 (13)0.0002 (14)0.0006 (12)
C7B0.0155 (17)0.0153 (16)0.0237 (18)−0.0002 (13)−0.0012 (13)−0.0028 (13)
C8B0.0188 (18)0.0181 (16)0.0204 (17)−0.0015 (14)0.0005 (14)−0.0018 (13)
C9B0.0177 (18)0.0219 (16)0.0204 (16)−0.0029 (14)0.0015 (14)−0.0035 (14)
C10B0.0217 (19)0.0229 (17)0.027 (2)0.0011 (15)−0.0024 (15)0.0000 (15)
C11B0.028 (2)0.0220 (18)0.0240 (18)−0.0030 (15)−0.0011 (16)0.0041 (14)
C12B0.025 (2)0.0319 (19)0.0201 (17)−0.0053 (16)0.0006 (15)0.0014 (15)
C13B0.025 (2)0.0270 (17)0.0222 (18)0.0012 (16)0.0045 (16)−0.0037 (14)
C14B0.025 (2)0.0201 (16)0.0231 (18)0.0018 (15)−0.0015 (15)−0.0001 (14)
C15B0.0212 (19)0.0185 (16)0.0250 (18)0.0035 (14)0.0011 (15)−0.0018 (14)

Geometric parameters (Å, °)

O2A—C8A1.229 (5)O2B—C8B1.237 (5)
N1A—C7A1.296 (5)N1B—C7B1.292 (5)
N1A—N2A1.388 (4)N1B—N2B1.389 (4)
N2A—C8A1.351 (5)N2B—C8B1.356 (5)
N2A—H2NA0.9145N2B—H2NB0.7271
C1A—C2A1.385 (5)C1B—C2B1.384 (5)
C1A—C6A1.406 (5)C1B—C6B1.397 (5)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.385 (6)C2B—C3B1.395 (6)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.392 (6)C3B—C4B1.387 (5)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.382 (5)C4B—C5B1.381 (5)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.400 (5)C5B—C6B1.404 (5)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.492 (5)C6B—C7B1.495 (5)
C7A—C15A1.491 (5)C7B—C15B1.498 (5)
C8A—C9A1.499 (5)C8B—C9B1.509 (5)
C9A—C10A1.396 (5)C9B—C14B1.382 (5)
C9A—C14A1.399 (5)C9B—C10B1.406 (5)
C10A—C11A1.388 (6)C10B—C11B1.384 (6)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.385 (6)C11B—C12B1.389 (6)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.386 (6)C12B—C13B1.387 (6)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.385 (5)C13B—C14B1.401 (5)
C13A—H13A0.9300C13B—H13B0.9300
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C7A—N1A—N2A117.0 (3)C7B—N1B—N2B117.1 (3)
C8A—N2A—N1A116.6 (3)C8B—N2B—N1B116.1 (3)
C8A—N2A—H2NA120.6C8B—N2B—H2NB114.2
N1A—N2A—H2NA117.0N1B—N2B—H2NB129.5
C2A—C1A—C6A120.7 (4)C2B—C1B—C6B120.5 (4)
C2A—C1A—H1AA119.6C2B—C1B—H1BA119.8
C6A—C1A—H1AA119.6C6B—C1B—H1BA119.8
C3A—C2A—C1A120.5 (4)C1B—C2B—C3B120.2 (4)
C3A—C2A—H2AA119.7C1B—C2B—H2BA119.9
C1A—C2A—H2AA119.7C3B—C2B—H2BA119.9
C2A—C3A—C4A119.5 (4)C4B—C3B—C2B119.7 (4)
C2A—C3A—H3AA120.3C4B—C3B—H3BA120.1
C4A—C3A—H3AA120.3C2B—C3B—H3BA120.1
C5A—C4A—C3A120.2 (4)C5B—C4B—C3B120.2 (4)
C5A—C4A—H4AA119.9C5B—C4B—H4BA119.9
C3A—C4A—H4AA119.9C3B—C4B—H4BA119.9
C4A—C5A—C6A121.1 (4)C4B—C5B—C6B120.6 (3)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.7
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.7
C5A—C6A—C1A117.9 (3)C1B—C6B—C5B118.8 (3)
C5A—C6A—C7A121.1 (3)C1B—C6B—C7B120.6 (3)
C1A—C6A—C7A121.0 (3)C5B—C6B—C7B120.6 (3)
N1A—C7A—C15A126.3 (3)N1B—C7B—C6B114.5 (3)
N1A—C7A—C6A114.3 (3)N1B—C7B—C15B126.2 (3)
C15A—C7A—C6A119.4 (3)C6B—C7B—C15B119.2 (3)
O2A—C8A—N2A122.4 (3)O2B—C8B—N2B122.6 (3)
O2A—C8A—C9A119.5 (3)O2B—C8B—C9B119.3 (3)
N2A—C8A—C9A118.1 (3)N2B—C8B—C9B118.1 (3)
C10A—C9A—C14A119.2 (3)C14B—C9B—C10B119.7 (4)
C10A—C9A—C8A116.7 (3)C14B—C9B—C8B123.3 (3)
C14A—C9A—C8A124.1 (3)C10B—C9B—C8B116.9 (3)
C11A—C10A—C9A120.2 (4)C11B—C10B—C9B119.8 (4)
C11A—C10A—H10A119.9C11B—C10B—H10B120.1
C9A—C10A—H10A119.9C9B—C10B—H10B120.1
C12A—C11A—C10A120.2 (4)C10B—C11B—C12B120.3 (4)
C12A—C11A—H11A119.9C10B—C11B—H11B119.9
C10A—C11A—H11A119.9C12B—C11B—H11B119.9
C11A—C12A—C13A119.7 (4)C13B—C12B—C11B120.4 (4)
C11A—C12A—H12A120.1C13B—C12B—H12B119.8
C13A—C12A—H12A120.1C11B—C12B—H12B119.8
C14A—C13A—C12A120.6 (4)C12B—C13B—C14B119.4 (4)
C14A—C13A—H13A119.7C12B—C13B—H13B120.3
C12A—C13A—H13A119.7C14B—C13B—H13B120.3
C13A—C14A—C9A120.0 (4)C9B—C14B—C13B120.4 (4)
C13A—C14A—H14A120.0C9B—C14B—H14B119.8
C9A—C14A—H14A120.0C13B—C14B—H14B119.8
C7A—C15A—H15A109.5C7B—C15B—H15D109.5
C7A—C15A—H15B109.5C7B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C7A—C15A—H15C109.5C7B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C7A—N1A—N2A—C8A167.6 (3)C7B—N1B—N2B—C8B166.7 (3)
C6A—C1A—C2A—C3A0.0 (6)C6B—C1B—C2B—C3B0.7 (6)
C1A—C2A—C3A—C4A0.7 (6)C1B—C2B—C3B—C4B−0.3 (6)
C2A—C3A—C4A—C5A−1.0 (6)C2B—C3B—C4B—C5B−0.5 (6)
C3A—C4A—C5A—C6A0.6 (6)C3B—C4B—C5B—C6B0.9 (6)
C4A—C5A—C6A—C1A0.1 (6)C2B—C1B—C6B—C5B−0.3 (6)
C4A—C5A—C6A—C7A−178.3 (3)C2B—C1B—C6B—C7B178.1 (4)
C2A—C1A—C6A—C5A−0.4 (6)C4B—C5B—C6B—C1B−0.5 (6)
C2A—C1A—C6A—C7A178.0 (3)C4B—C5B—C6B—C7B−178.9 (4)
N2A—N1A—C7A—C15A−4.2 (6)N2B—N1B—C7B—C6B174.9 (3)
N2A—N1A—C7A—C6A176.2 (3)N2B—N1B—C7B—C15B−3.6 (6)
C5A—C6A—C7A—N1A6.8 (5)C1B—C6B—C7B—N1B−170.8 (3)
C1A—C6A—C7A—N1A−171.5 (3)C5B—C6B—C7B—N1B7.6 (5)
C5A—C6A—C7A—C15A−172.8 (4)C1B—C6B—C7B—C15B7.8 (5)
C1A—C6A—C7A—C15A8.8 (5)C5B—C6B—C7B—C15B−173.8 (3)
N1A—N2A—C8A—O2A−9.0 (5)N1B—N2B—C8B—O2B−8.4 (5)
N1A—N2A—C8A—C9A174.2 (3)N1B—N2B—C8B—C9B172.6 (3)
O2A—C8A—C9A—C10A19.1 (5)O2B—C8B—C9B—C14B−158.2 (4)
N2A—C8A—C9A—C10A−164.0 (3)N2B—C8B—C9B—C14B20.9 (6)
O2A—C8A—C9A—C14A−158.9 (4)O2B—C8B—C9B—C10B17.6 (5)
N2A—C8A—C9A—C14A18.0 (5)N2B—C8B—C9B—C10B−163.3 (3)
C14A—C9A—C10A—C11A0.6 (6)C14B—C9B—C10B—C11B−1.2 (6)
C8A—C9A—C10A—C11A−177.4 (4)C8B—C9B—C10B—C11B−177.2 (4)
C9A—C10A—C11A—C12A−1.2 (6)C9B—C10B—C11B—C12B0.0 (6)
C10A—C11A—C12A—C13A1.4 (6)C10B—C11B—C12B—C13B−0.2 (6)
C11A—C12A—C13A—C14A−1.1 (6)C11B—C12B—C13B—C14B1.5 (6)
C12A—C13A—C14A—C9A0.5 (6)C10B—C9B—C14B—C13B2.6 (6)
C10A—C9A—C14A—C13A−0.3 (6)C8B—C9B—C14B—C13B178.3 (4)
C8A—C9A—C14A—C13A177.6 (4)C12B—C13B—C14B—C9B−2.7 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O2Ai0.911.952.857 (4)170
N2B—H2NB···O2Bii0.732.172.866 (4)161
C14A—H14A···O2Ai0.932.383.108 (5)135
C14B—H14B···O2Bii0.932.383.113 (5)135
C15A—H15A···N2A0.962.472.811 (5)100
C15A—H15A···O2Ai0.962.583.053 (5)110
C15B—H15D···N2B0.962.442.812 (5)103
C15B—H15D···O2Bii0.962.453.038 (5)120
C1A—H1AA···Cg1ii0.932.963.729 (4)141
C4A—H4AA···Cg1iii0.932.953.724 (5)141
C1B—H1BA···Cg2i0.932.883.726 (4)141
C10A—H10A···Cg3iv0.933.313.993 (4)132
C10B—H10B···Cg4v0.933.163.847 (4)132
C4B—H4BA···Cg2vi0.932.943.714 (4)141
C13A—H13A···Cg3i0.933.053.674 (4)126
C13B—H13B···Cg4ii0.933.073.755 (4)132

Symmetry codes: (i) x+1/2, −y, z; (ii) x+1/2, −y+1, z; (iii) x−1/2, −y, z; (iv) x−1/2, −y−1, z; (v) x−1/2, −y+2, z; (vi) x−1/2, −y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2108).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bratenko, M. K., Chornous, V. A., Voloshin, N. P. & Vovk, M. V. (1999). Chem. Heterocycl. Compd, 35, 1075–1077.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem.42, 425–429. [PubMed]
  • Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Sridhar, R. & Perumal, P. T. (2003). Syn. Commun.33, 1483–1488.
  • Zhang, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett.17, 3774–3777. [PubMed]

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