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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2074
https://doi.org/10.1107/S1600536812025548

N′-(3-Fluoro­benzyl­­idene)-2-methyl­benzohydrazide

Ying Song,a,b Jian-Long Zhao,b Jan-Gang Wang,b Fei Lu,a Hong Lua* and Shi-Peng Lib

aThe 1st Affiliated Hospital of Henan University of Science & Technology, Luoyang Henan 471003, People's Republic of China, and bMedical College, Henan University of Science & Technology, Luoyang Henan 471003, People's Republic of China
*Correspondence e-mail: sying20096@126.com

(Received 1 June 2012; accepted 5 June 2012; online 13 June 2012)

The asymmetric unit of the title compound, C15H13FN2O, contains two independent mol­ecules with different conformations; the two aromatic rings in the independent mol­ecules form dihedral angles of 85.3 (2) and 10.0 (2)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains along [100].

Related literature

For related structures, see: Xu et al. (2011[Xu, C.-B., Wang, Z.-G., Nan, Y., Yuan, L., Wang, R. & Zhang, S.-X. (2011). Acta Cryst. E67, o70.]); Wang et al. (2012[Wang, D.-Y., Meng, X.-F. & Ma, J.-J. (2012). Acta Cryst. E68, o21.]); Hu & Liu (2012[Hu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.]). For the biological activity of benzohydra­zones, see: Zhang et al. (2012[Zhang, M., Xian, D.-M., Li, H.-H., Zhang, J.-C. & You, Z.-L. (2012). Aust. J. Chem. 65, 343-350.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13FN2O

  • Mr = 256.27

  • Triclinic, [P \overline 1]

  • a = 7.8516 (13) Å

  • b = 8.1466 (13) Å

  • c = 21.158 (3) Å

  • α = 86.668 (2)°

  • β = 85.806 (2)°

  • γ = 79.772 (2)°

  • V = 1326.9 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.17 × 0.15 × 0.15 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.986

  • 9780 measured reflections

  • 4844 independent reflections

  • 4067 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.126

  • S = 1.06

  • 4844 reflections

  • 351 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4⋯O1 0.89 (1) 1.93 (1) 2.8115 (15) 168 (2)
N2—H2⋯O2i 0.89 (1) 2.08 (1) 2.9185 (16) 157 (2)
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025548/cv5308sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025548/cv5308Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025548/cv5308Isup3.cml

checkCIF report


Comment top

Benzohydrazones derived from the condensation reactions of benzohydrazides with carbonyl-containing compounds have been proved to have antimicrobial and antitumor activities (Zhang et al., 2012). Herewith we present the title compound (I), which is a new benzohydrazone derivative.

The asymmetric unit of the title compound contains two independent molecules, A and B, respectively, with different conformations (Fig. 1) - two aromatic rings in the independent molecules form the dihedral angles of 85.3 (2)° (B) and 10.0 (2)° (A), respectively. All the bond lengths and angles are normal and correspond to those observed in the related structures (Wang et al., 2012; Hu & Liu, 2012; Xu et al., 2011). In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains in [100] (Fig. 2).

Related literature top

For related structures, see: Xu et al. (2011); Wang et al. (2012); Hu & Liu (2012). For the biological activity of benzohydrazones, see: Zhang et al. (2012).

Experimental top

Equimolar quantities (1 mmol each) of 3-fluorohlorobenzaldehyde and 2-methylbenzohydrazide were mixed in 50 mL methanol. The materials were stirred at room temperature for 1 h to give a clear colorless solution. Colourless block-like single crystals were obtained after a few days.

Refinement top

Atom H2 located from a Fourier map was isotropically refined, with N–H distance restrained to 0.90 (1) Å. C-bound H atoms were positioned geometrically and treated as riding on their parent atoms, with C–H distances of 0.93–0.96 Å, and with Uiso(H) set to 1.2–1.5 Ueq(C).

Structure description top

Benzohydrazones derived from the condensation reactions of benzohydrazides with carbonyl-containing compounds have been proved to have antimicrobial and antitumor activities (Zhang et al., 2012). Herewith we present the title compound (I), which is a new benzohydrazone derivative.

The asymmetric unit of the title compound contains two independent molecules, A and B, respectively, with different conformations (Fig. 1) - two aromatic rings in the independent molecules form the dihedral angles of 85.3 (2)° (B) and 10.0 (2)° (A), respectively. All the bond lengths and angles are normal and correspond to those observed in the related structures (Wang et al., 2012; Hu & Liu, 2012; Xu et al., 2011). In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains in [100] (Fig. 2).

For related structures, see: Xu et al. (2011); Wang et al. (2012); Hu & Liu (2012). For the biological activity of benzohydrazones, see: Zhang et al. (2012).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Conformations of two independent molecules in (I). Displacement ellipsoids are drawn with 30% probability level.
[Figure 2] Fig. 2. Molecular packing diagram of (I), viewed down the b axis. Hydrogen bonds are shown as thin dashed lines. C-bound H atoms omitted for clarity
N'-(3-Fluorobenzylidene)-2-methylbenzohydrazide top
Crystal data top
C15H13FN2OZ = 4
Mr = 256.27F(000) = 536
Triclinic, P1Dx = 1.283 Mg m−3
a = 7.8516 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1466 (13) ÅCell parameters from 5461 reflections
c = 21.158 (3) Åθ = 2.6–27.0°
α = 86.668 (2)°µ = 0.09 mm−1
β = 85.806 (2)°T = 298 K
γ = 79.772 (2)°Block, colourless
V = 1326.9 (4) Å30.17 × 0.15 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4844 independent reflections
Radiation source: fine-focus sealed tube4067 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.985, Tmax = 0.986k = −9→9
9780 measured reflectionsl = −25→25
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0719P)2 + 0.1885P]
where P = (Fo2 + 2Fc2)/3
4844 reflections(Δ/σ)max = 0.001
351 parametersΔρmax = 0.18 e Å−3
2 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C15H13FN2Oγ = 79.772 (2)°
Mr = 256.27V = 1326.9 (4) Å3
Triclinic, P1Z = 4
a = 7.8516 (13) ÅMo Kα radiation
b = 8.1466 (13) ŵ = 0.09 mm−1
c = 21.158 (3) ÅT = 298 K
α = 86.668 (2)°0.17 × 0.15 × 0.15 mm
β = 85.806 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4844 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4067 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.986Rint = 0.019
9780 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0412 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.18 e Å−3
4844 reflectionsΔρmin = −0.21 e Å−3
351 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F10.49294 (13)−0.42660 (13)0.33943 (6)0.0741 (3)
F20.1795 (2)−0.2449 (2)0.48808 (6)0.1094 (5)
N10.86796 (15)0.01129 (14)0.27473 (6)0.0424 (3)
N20.95208 (15)0.13387 (14)0.24586 (6)0.0432 (3)
N30.38019 (14)0.05746 (15)0.28693 (5)0.0409 (3)
N40.46524 (15)0.09877 (15)0.23035 (5)0.0419 (3)
O10.70015 (12)0.31769 (12)0.24076 (5)0.0480 (3)
O20.27172 (13)0.01591 (14)0.17023 (5)0.0523 (3)
C10.72163 (19)−0.27856 (18)0.31576 (7)0.0450 (3)
H10.6494−0.19870.29220.054*
C20.6609 (2)−0.41226 (19)0.34545 (8)0.0501 (4)
C30.7605 (2)−0.5331 (2)0.38078 (8)0.0591 (4)
H30.7146−0.62220.40040.071*
C40.9300 (2)−0.5191 (2)0.38638 (8)0.0614 (4)
H4A1.0003−0.59930.41050.074*
C50.9978 (2)−0.38669 (19)0.35649 (8)0.0516 (4)
H51.1137−0.37980.36000.062*
C60.89381 (18)−0.26449 (17)0.32148 (6)0.0410 (3)
C70.96683 (18)−0.12343 (17)0.29124 (6)0.0417 (3)
H71.0863−0.13250.28410.050*
C80.85819 (17)0.28570 (17)0.23110 (6)0.0384 (3)
C90.96279 (17)0.41235 (16)0.20355 (6)0.0396 (3)
C100.8958 (2)0.53546 (18)0.15847 (7)0.0484 (4)
C111.0015 (2)0.6487 (2)0.13572 (9)0.0619 (5)
H110.96060.73030.10530.074*
C121.1644 (3)0.6444 (2)0.15654 (9)0.0660 (5)
H121.23150.72210.14010.079*
C131.2274 (2)0.5256 (2)0.20142 (9)0.0606 (4)
H131.33680.52270.21600.073*
C141.12632 (19)0.41004 (18)0.22478 (7)0.0472 (3)
H141.16880.32930.25530.057*
C150.7180 (3)0.5522 (3)0.13424 (10)0.0746 (6)
H15A0.63220.59010.16730.112*
H15B0.70080.44570.12120.112*
H15C0.70750.63140.09870.112*
C160.2917 (2)−0.0634 (2)0.41323 (7)0.0553 (4)
H160.2941−0.14000.38210.066*
C170.2317 (2)−0.0961 (3)0.47414 (9)0.0698 (5)
C180.2250 (3)0.0105 (3)0.52174 (9)0.0813 (7)
H180.1828−0.01630.56250.098*
C190.2823 (3)0.1588 (3)0.50772 (9)0.0807 (6)
H190.27890.23380.53950.097*
C200.3458 (2)0.1984 (3)0.44652 (8)0.0649 (5)
H200.38550.29870.43760.078*
C210.34927 (18)0.0876 (2)0.39894 (7)0.0477 (4)
C220.41875 (18)0.1272 (2)0.33473 (7)0.0469 (3)
H220.49260.20510.32890.056*
C230.40720 (17)0.06825 (16)0.17440 (6)0.0397 (3)
C240.52512 (18)0.10606 (17)0.11860 (7)0.0424 (3)
C250.4604 (2)0.1922 (2)0.06360 (7)0.0541 (4)
C260.5812 (3)0.2257 (3)0.01535 (9)0.0756 (6)
H260.54190.2832−0.02150.091*
C270.7564 (3)0.1768 (3)0.02029 (10)0.0811 (6)
H270.83340.2020−0.01290.097*
C280.8183 (2)0.0910 (2)0.07389 (9)0.0670 (5)
H280.93700.05670.07720.080*
C290.70265 (19)0.0561 (2)0.12286 (8)0.0506 (4)
H290.7441−0.00170.15940.061*
C300.2710 (2)0.2514 (3)0.05541 (9)0.0746 (6)
H30A0.25660.34560.02570.112*
H30B0.21330.28340.09550.112*
H30C0.22190.16290.03980.112*
H21.0634 (14)0.108 (3)0.2319 (9)0.080*
H40.551 (2)0.157 (2)0.2320 (10)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0524 (6)0.0685 (6)0.1057 (8)−0.0265 (5)−0.0017 (5)0.0042 (6)
F20.1345 (12)0.1237 (11)0.0735 (8)−0.0505 (10)0.0027 (7)0.0419 (8)
N10.0406 (6)0.0401 (6)0.0470 (7)−0.0131 (5)0.0031 (5)0.0061 (5)
N20.0343 (6)0.0405 (6)0.0540 (7)−0.0104 (5)0.0045 (5)0.0083 (5)
N30.0335 (6)0.0500 (7)0.0384 (6)−0.0091 (5)0.0024 (5)0.0044 (5)
N40.0350 (6)0.0532 (7)0.0392 (6)−0.0164 (5)0.0043 (5)0.0025 (5)
O10.0339 (5)0.0459 (6)0.0639 (7)−0.0102 (4)0.0031 (4)0.0015 (5)
O20.0464 (6)0.0652 (7)0.0511 (6)−0.0272 (5)0.0032 (5)−0.0064 (5)
C10.0458 (8)0.0395 (7)0.0492 (8)−0.0073 (6)−0.0031 (6)0.0024 (6)
C20.0465 (8)0.0483 (8)0.0571 (9)−0.0151 (7)0.0019 (7)−0.0028 (7)
C30.0700 (11)0.0468 (9)0.0621 (10)−0.0209 (8)0.0000 (8)0.0119 (7)
C40.0698 (11)0.0504 (9)0.0622 (10)−0.0090 (8)−0.0134 (8)0.0197 (8)
C50.0493 (9)0.0503 (9)0.0549 (9)−0.0086 (7)−0.0090 (7)0.0067 (7)
C60.0449 (8)0.0392 (7)0.0384 (7)−0.0082 (6)0.0003 (6)0.0006 (6)
C70.0376 (7)0.0441 (8)0.0433 (7)−0.0096 (6)−0.0001 (6)0.0024 (6)
C80.0359 (7)0.0406 (7)0.0395 (7)−0.0109 (6)0.0009 (5)0.0008 (5)
C90.0374 (7)0.0371 (7)0.0441 (7)−0.0092 (5)0.0051 (6)−0.0011 (6)
C100.0503 (9)0.0420 (8)0.0506 (8)−0.0069 (6)0.0034 (7)0.0050 (6)
C110.0706 (12)0.0449 (9)0.0662 (11)−0.0111 (8)0.0133 (9)0.0118 (8)
C120.0708 (12)0.0497 (9)0.0805 (12)−0.0297 (8)0.0199 (9)0.0004 (9)
C130.0490 (9)0.0605 (10)0.0776 (12)−0.0259 (8)0.0060 (8)−0.0084 (9)
C140.0416 (8)0.0456 (8)0.0556 (9)−0.0129 (6)0.0016 (6)−0.0008 (7)
C150.0657 (12)0.0769 (13)0.0791 (13)−0.0114 (10)−0.0182 (10)0.0291 (10)
C160.0528 (9)0.0725 (11)0.0402 (8)−0.0119 (8)−0.0050 (7)0.0075 (7)
C170.0599 (11)0.0974 (14)0.0500 (10)−0.0156 (10)−0.0042 (8)0.0214 (10)
C180.0639 (12)0.133 (2)0.0398 (10)−0.0032 (12)0.0036 (8)0.0069 (11)
C190.0677 (12)0.1221 (19)0.0475 (10)0.0027 (12)−0.0010 (9)−0.0255 (11)
C200.0539 (10)0.0865 (13)0.0546 (10)−0.0092 (9)−0.0029 (8)−0.0151 (9)
C210.0337 (7)0.0681 (10)0.0394 (8)−0.0041 (6)−0.0039 (6)−0.0008 (7)
C220.0379 (8)0.0583 (9)0.0460 (8)−0.0137 (6)0.0001 (6)−0.0012 (7)
C230.0375 (7)0.0390 (7)0.0429 (7)−0.0099 (6)0.0035 (6)−0.0019 (6)
C240.0434 (8)0.0437 (7)0.0407 (7)−0.0117 (6)0.0060 (6)−0.0054 (6)
C250.0562 (9)0.0662 (10)0.0395 (8)−0.0121 (8)0.0042 (7)−0.0032 (7)
C260.0768 (13)0.0993 (15)0.0448 (10)−0.0104 (11)0.0115 (9)0.0120 (9)
C270.0740 (13)0.1000 (15)0.0625 (12)−0.0154 (11)0.0323 (10)0.0091 (11)
C280.0482 (9)0.0761 (12)0.0714 (12)−0.0075 (8)0.0223 (8)−0.0017 (9)
C290.0438 (8)0.0538 (9)0.0518 (9)−0.0068 (7)0.0084 (7)−0.0012 (7)
C300.0635 (12)0.1075 (16)0.0501 (10)−0.0086 (11)−0.0095 (8)0.0069 (10)
Geometric parameters (Å, º) top
F1—C21.3598 (18)C13—C141.384 (2)
F2—C171.357 (2)C13—H130.9300
N1—C71.2735 (18)C14—H140.9300
N1—N21.3824 (15)C15—H15A0.9600
N2—C81.3549 (18)C15—H15B0.9600
N2—H20.894 (9)C15—H15C0.9600
N3—C221.2689 (19)C16—C171.367 (2)
N3—N41.3815 (15)C16—C211.394 (2)
N4—C231.3506 (18)C16—H160.9300
N4—H40.893 (9)C17—C181.360 (3)
O1—C81.2263 (16)C18—C191.372 (3)
O2—C231.2249 (16)C18—H180.9300
C1—C21.367 (2)C19—C201.394 (3)
C1—C61.391 (2)C19—H190.9300
C1—H10.9300C20—C211.386 (2)
C2—C31.366 (2)C20—H200.9300
C3—C41.370 (3)C21—C221.467 (2)
C3—H30.9300C22—H220.9300
C4—C51.387 (2)C23—C241.4984 (18)
C4—H4A0.9300C24—C291.389 (2)
C5—C61.386 (2)C24—C251.404 (2)
C5—H50.9300C25—C261.390 (2)
C6—C71.4675 (19)C25—C301.499 (3)
C7—H70.9300C26—C271.373 (3)
C8—C91.4966 (18)C26—H260.9300
C9—C141.388 (2)C27—C281.371 (3)
C9—C101.403 (2)C27—H270.9300
C10—C111.390 (2)C28—C291.378 (2)
C10—C151.503 (2)C28—H280.9300
C11—C121.377 (3)C29—H290.9300
C11—H110.9300C30—H30A0.9600
C12—C131.369 (3)C30—H30B0.9600
C12—H120.9300C30—H30C0.9600
C7—N1—N2115.08 (12)H15A—C15—H15B109.5
C8—N2—N1119.04 (11)C10—C15—H15C109.5
C8—N2—H2120.3 (13)H15A—C15—H15C109.5
N1—N2—H2120.0 (13)H15B—C15—H15C109.5
C22—N3—N4114.56 (12)C17—C16—C21118.33 (17)
C23—N4—N3120.56 (11)C17—C16—H16120.8
C23—N4—H4121.3 (13)C21—C16—H16120.8
N3—N4—H4117.7 (13)F2—C17—C18118.24 (17)
C2—C1—C6118.59 (14)F2—C17—C16118.05 (19)
C2—C1—H1120.7C18—C17—C16123.7 (2)
C6—C1—H1120.7C17—C18—C19117.97 (18)
F1—C2—C3118.08 (14)C17—C18—H18121.0
F1—C2—C1118.55 (14)C19—C18—H18121.0
C3—C2—C1123.37 (15)C18—C19—C20120.86 (19)
C2—C3—C4117.99 (14)C18—C19—H19119.6
C2—C3—H3121.0C20—C19—H19119.6
C4—C3—H3121.0C21—C20—C19119.7 (2)
C3—C4—C5120.65 (15)C21—C20—H20120.2
C3—C4—H4A119.7C19—C20—H20120.2
C5—C4—H4A119.7C20—C21—C16119.46 (15)
C6—C5—C4120.37 (15)C20—C21—C22119.93 (16)
C6—C5—H5119.8C16—C21—C22120.58 (14)
C4—C5—H5119.8N3—C22—C21121.35 (13)
C5—C6—C1119.02 (13)N3—C22—H22119.3
C5—C6—C7119.63 (13)C21—C22—H22119.3
C1—C6—C7121.36 (13)O2—C23—N4123.05 (12)
N1—C7—C6120.57 (13)O2—C23—C24124.02 (13)
N1—C7—H7119.7N4—C23—C24112.93 (11)
C6—C7—H7119.7C29—C24—C25120.14 (13)
O1—C8—N2122.54 (12)C29—C24—C23118.20 (13)
O1—C8—C9122.65 (12)C25—C24—C23121.65 (13)
N2—C8—C9114.79 (11)C26—C25—C24117.09 (16)
C14—C9—C10119.96 (13)C26—C25—C30119.45 (16)
C14—C9—C8118.96 (12)C24—C25—C30123.45 (14)
C10—C9—C8121.05 (12)C27—C26—C25122.25 (18)
C11—C10—C9117.18 (14)C27—C26—H26118.9
C11—C10—C15118.83 (15)C25—C26—H26118.9
C9—C10—C15123.98 (14)C28—C27—C26120.26 (16)
C12—C11—C10122.50 (16)C28—C27—H27119.9
C12—C11—H11118.8C26—C27—H27119.9
C10—C11—H11118.8C27—C28—C29119.17 (17)
C13—C12—C11119.88 (15)C27—C28—H28120.4
C13—C12—H12120.1C29—C28—H28120.4
C11—C12—H12120.1C28—C29—C24121.09 (16)
C12—C13—C14119.22 (16)C28—C29—H29119.5
C12—C13—H13120.4C24—C29—H29119.5
C14—C13—H13120.4C25—C30—H30A109.5
C13—C14—C9121.24 (15)C25—C30—H30B109.5
C13—C14—H14119.4H30A—C30—H30B109.5
C9—C14—H14119.4C25—C30—H30C109.5
C10—C15—H15A109.5H30A—C30—H30C109.5
C10—C15—H15B109.5H30B—C30—H30C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.89 (1)1.93 (1)2.8115 (15)168 (2)
N2—H2···O2i0.89 (1)2.08 (1)2.9185 (16)157 (2)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H13FN2O
Mr256.27
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.8516 (13), 8.1466 (13), 21.158 (3)
α, β, γ (°)86.668 (2), 85.806 (2), 79.772 (2)
V (Å3)1326.9 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.17 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.985, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections		9780, 4844, 4067
Rint0.019
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.126, 1.06
No. of reflections4844
No. of parameters351
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.893 (9)1.931 (10)2.8115 (15)168 (2)
N2—H2···O2i0.894 (9)2.076 (12)2.9185 (16)156.7 (18)
Symmetry code: (i) x+1, y, z.
 

References

First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, D.-Y., Meng, X.-F. & Ma, J.-J. (2012). Acta Cryst. E68, o21.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationXu, C.-B., Wang, Z.-G., Nan, Y., Yuan, L., Wang, R. & Zhang, S.-X. (2011). Acta Cryst. E67, o70.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationZhang, M., Xian, D.-M., Li, H.-H., Zhang, J.-C. & You, Z.-L. (2012). Aust. J. Chem. 65, 343–350.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2074
https://doi.org/10.1107/S1600536812025548
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