N-Cyclo­hexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide

Tian, D.-L.; Luo, G.; Chen, H.; Tang, X.-W.; Liu, Y.-F.

doi:10.1107/S1600536811024299

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1851

doi:10.1107/S1600536811024299

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N-Cyclohexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide

Dan-Li Tian,^a Gang Luo,^a Hong Chen,^b,^c ^* Xiao-Wei Tang ^b and Yong-Feng Liu ^b

^aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China, ^bMedical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China, and ^cTianjin Key Laboratory for Biomarkers of Occupational, and Environmental Hazards, Tianjin 300162, People's Republic of China
^*Correspondence e-mail: tjch2010@yahoo.cn

(Received 17 June 2011; accepted 21 June 2011; online 30 June 2011)

In title compound, C₁₆H₁₇FN₂O₂, the cyclohexane ring adopts a chair conformation.. The crystal packing is stabilized by weak π–π stacking interactions [centroid–centroid distance = 3.503 (5) Å] and intermolecular C—H⋯O, N—H⋯O and N—H⋯F hydrogen-bond interactions.

Related literature

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008 ); Chai et al. (2006 ); Radwan et al. (2007 ); Karthikeyan et al. (2009 ). For the preparation, see: Bacher et al. (2001 ). For bond-length and angle data for similar structures, see: Liu et al. (2011 ); Sonar et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₇FN₂O₂
M_r = 288.32
Monoclinic, P 2₁ /c
a = 11.5065 (15) Å
b = 9.7666 (12) Å
c = 12.3139 (16) Å
β = 96.639 (5)°
V = 1374.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.980, T_max = 0.988
18432 measured reflections
3717 independent reflections
3007 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.04
3717 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F1ⁱ	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1⋯O2ⁱⁱ	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8⋯O1ⁱⁱⁱ	0.95	2.31	3.0586 (12)	136
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024299/hg5056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024299/hg5056Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024299/hg5056Isup3.cml

checkCIF report

Comment top

Indole and their derivatives are well known as substances with biologically activity such as anti-cancer (Souli et al., 2008), anti-virus(Chai et al., 2006), anti-tubercular (Karthikeyan et al., 2009), and anti-inflammatory (Radwan et al., 2007). In recent years, our recent study is paying attention to synthesize different kinds of indole derivatives with improved bioactivities. In this paper, we reported the crystal structure of title compound.

In title compound, C₁₆H₁₇FN₂O₂, bond lengths and angles are normal and in good agreement with those reported previously (Liu et al., 2011; Sonar, et al., 2006). The cyclohexane ring (C11—C16) adopts a chair conformation. π—π interactions are indicated by the short distance (Cg1···Cg2 distance of 3.503 (5) Å, symmetry code: -x,1 - y,-z) between the centroids of the pyrrole ring (N1/C1/C6—C8) (Cg1) and benzene ring C1—C6 (Cg2) (Table 1). There are weaker C—H···O N—H···F and N—H···O intermolecular interactions, which stabilized the structure (Table 1)

Related literature top

For the biological activity of the title compound and its derivatives, see: Souli et al. (2008); Chai et al. (2006); Radwan et al. (2007); Karthikeyan et al. (2009). For the preparation, see: Bacher et al. (2001). For bond-length and angle data for similar structures, see: Liu et al. (2011); Sonar et al. (2006).

Experimental top

The target compound was synthesized by two steps. Oxalyl chloride was added dropwise to 5-fluorine indole in dry ether. 5-fluorine indole-3-yl-glyoxyl chloride which was the crude product, cyclohexane, two drops of triethylamine were in dry dichloromethane. The reaction mixture was washed with water and dried over Na₂SO₄ and concentrated in vacuo (Bacher et al., 2001). The residue was resolved in a methanol solution. Slow evaporation over two week at room temperature gave light-white crystals suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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

Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.

N-Cyclohexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide top

Crystal data top

C₁₆H₁₇FN₂O₂	F(000) = 608
M_r = 288.32	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5346 reflections
a = 11.5065 (15) Å	θ = 1.7–29.1°
b = 9.7666 (12) Å	µ = 0.10 mm⁻¹
c = 12.3139 (16) Å	T = 113 K
β = 96.639 (5)°	Prism, colorless
V = 1374.5 (3) Å³	0.20 × 0.16 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3717 independent reflections
Radiation source: rotating anode	3007 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.035
Detector resolution: 14.63 pixels mm^-1	θ_max = 29.2°, θ_min = 2.7°
ω and ϕ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→13
T_min = 0.980, T_max = 0.988	l = −16→16
18432 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0605P)²] where P = (F_o² + 2F_c²)/3
3717 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₇FN₂O₂	V = 1374.5 (3) Å³
M_r = 288.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5065 (15) Å	µ = 0.10 mm⁻¹
b = 9.7666 (12) Å	T = 113 K
c = 12.3139 (16) Å	0.20 × 0.16 × 0.12 mm
β = 96.639 (5)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3717 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3007 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.988	R_int = 0.035
18432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
3717 reflections	Δρ_min = −0.28 e Å⁻³
198 parameters

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	U_iso*/U_eq
F1	−0.25500 (5)	1.05586 (6)	0.22558 (5)	0.02199 (16)
O1	0.03563 (6)	0.68310 (7)	0.38752 (6)	0.01933 (17)
O2	0.10442 (6)	0.59789 (7)	0.66261 (6)	0.01922 (17)
N1	−0.11616 (7)	0.93484 (9)	0.65153 (7)	0.01534 (18)
N2	0.18874 (7)	0.53328 (8)	0.51269 (7)	0.01509 (18)
C1	−0.16319 (8)	0.97805 (10)	0.54839 (8)	0.0138 (2)
C2	−0.24187 (9)	1.08328 (10)	0.51989 (8)	0.0164 (2)
H2A	−0.2737	1.1364	0.5739	0.020*
C3	−0.27217 (8)	1.10769 (10)	0.40949 (8)	0.0167 (2)
H3	−0.3255	1.1788	0.3859	0.020*
C4	−0.22354 (9)	1.02687 (10)	0.33359 (8)	0.0156 (2)
C5	−0.14663 (8)	0.92118 (9)	0.35915 (8)	0.0140 (2)
H5	−0.1162	0.8682	0.3042	0.017*
C6	−0.11544 (8)	0.89560 (9)	0.47050 (8)	0.01231 (19)
C7	−0.03768 (8)	0.79970 (10)	0.53188 (7)	0.01268 (19)
C8	−0.04120 (8)	0.83109 (9)	0.64156 (8)	0.0141 (2)
H8	0.0030	0.7858	0.7009	0.017*
C9	0.03360 (8)	0.69899 (10)	0.48630 (7)	0.01308 (19)
C10	0.11288 (8)	0.60472 (9)	0.56399 (8)	0.0135 (2)
C11	0.26943 (8)	0.43341 (10)	0.56915 (8)	0.0150 (2)
H11	0.2231	0.3700	0.6112	0.018*
C12	0.36197 (9)	0.50230 (11)	0.64966 (9)	0.0204 (2)
H12A	0.3235	0.5562	0.7034	0.024*
H12B	0.4092	0.5657	0.6099	0.024*
C13	0.44143 (10)	0.39422 (12)	0.70913 (9)	0.0249 (3)
H13A	0.5025	0.4399	0.7597	0.030*
H13B	0.3948	0.3352	0.7530	0.030*
C14	0.49948 (9)	0.30599 (11)	0.62842 (9)	0.0229 (2)
H14A	0.5538	0.3632	0.5912	0.028*
H14B	0.5457	0.2328	0.6688	0.028*
C15	0.40945 (9)	0.24164 (10)	0.54345 (9)	0.0205 (2)
H15A	0.3630	0.1735	0.5795	0.025*
H15B	0.4503	0.1930	0.4884	0.025*
C16	0.32700 (8)	0.34877 (10)	0.48594 (8)	0.0168 (2)
H16A	0.3716	0.4100	0.4418	0.020*
H16B	0.2659	0.3024	0.4358	0.020*
H1	−0.1231 (12)	0.9799 (14)	0.7178 (12)	0.043 (4)*
H2	0.1848 (11)	0.5448 (12)	0.4395 (11)	0.027 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0241 (3)	0.0273 (3)	0.0137 (3)	0.0058 (3)	−0.0016 (2)	0.0056 (2)
O1	0.0251 (4)	0.0224 (4)	0.0100 (3)	0.0067 (3)	0.0000 (3)	−0.0008 (3)
O2	0.0269 (4)	0.0197 (4)	0.0110 (3)	0.0042 (3)	0.0019 (3)	0.0041 (3)
N1	0.0181 (4)	0.0177 (4)	0.0103 (4)	−0.0015 (3)	0.0018 (3)	−0.0032 (3)
N2	0.0171 (4)	0.0157 (4)	0.0121 (4)	0.0022 (3)	−0.0002 (3)	0.0017 (3)
C1	0.0145 (4)	0.0148 (5)	0.0118 (4)	−0.0030 (4)	0.0008 (3)	−0.0013 (3)
C2	0.0154 (5)	0.0157 (5)	0.0187 (5)	−0.0010 (4)	0.0035 (4)	−0.0036 (4)
C3	0.0141 (5)	0.0144 (5)	0.0214 (5)	0.0009 (4)	0.0011 (4)	0.0006 (4)
C4	0.0160 (5)	0.0179 (5)	0.0123 (5)	−0.0020 (4)	−0.0013 (3)	0.0023 (4)
C5	0.0153 (5)	0.0148 (5)	0.0119 (5)	−0.0015 (4)	0.0013 (3)	−0.0011 (3)
C6	0.0129 (4)	0.0124 (4)	0.0116 (4)	−0.0022 (4)	0.0014 (3)	−0.0004 (3)
C7	0.0143 (4)	0.0132 (4)	0.0102 (4)	−0.0028 (4)	0.0002 (3)	0.0004 (3)
C8	0.0154 (4)	0.0150 (5)	0.0116 (5)	−0.0027 (4)	0.0006 (3)	−0.0001 (3)
C9	0.0149 (4)	0.0136 (4)	0.0102 (4)	−0.0024 (4)	−0.0006 (3)	0.0005 (3)
C10	0.0162 (5)	0.0116 (4)	0.0122 (4)	−0.0025 (4)	0.0000 (3)	0.0007 (3)
C11	0.0148 (5)	0.0143 (5)	0.0154 (5)	0.0006 (4)	−0.0010 (4)	0.0022 (4)
C12	0.0193 (5)	0.0202 (5)	0.0200 (5)	0.0004 (4)	−0.0041 (4)	−0.0017 (4)
C13	0.0211 (5)	0.0283 (6)	0.0230 (6)	0.0024 (5)	−0.0071 (4)	0.0016 (4)
C14	0.0163 (5)	0.0217 (5)	0.0295 (6)	0.0023 (4)	−0.0027 (4)	0.0053 (4)
C15	0.0173 (5)	0.0164 (5)	0.0277 (6)	0.0010 (4)	0.0020 (4)	0.0012 (4)
C16	0.0154 (5)	0.0162 (5)	0.0185 (5)	−0.0009 (4)	0.0007 (4)	0.0003 (4)

Geometric parameters (Å, º) top

F1—C4	1.3671 (11)	C7—C9	1.4358 (14)
O1—C9	1.2291 (11)	C8—H8	0.9500
O2—C10	1.2313 (12)	C9—C10	1.5470 (13)
N1—C8	1.3454 (13)	C11—C12	1.5249 (14)
N1—C1	1.3874 (12)	C11—C16	1.5261 (14)
N1—H1	0.939 (14)	C11—H11	1.0000
N2—C10	1.3324 (13)	C12—C13	1.5270 (14)
N2—C11	1.4655 (12)	C12—H12A	0.9900
N2—H2	0.905 (13)	C12—H12B	0.9900
C1—C2	1.3877 (14)	C13—C14	1.5265 (16)
C1—C6	1.4113 (13)	C13—H13A	0.9900
C2—C3	1.3846 (14)	C13—H13B	0.9900
C2—H2A	0.9500	C14—C15	1.5206 (14)
C3—C4	1.3895 (14)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.3723 (14)	C15—C16	1.5300 (13)
C5—C6	1.3992 (13)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.4466 (13)	C16—H16A	0.9900
C7—C8	1.3901 (13)	C16—H16B	0.9900

C8—N1—C1	109.38 (8)	N2—C11—C12	111.79 (8)
C8—N1—H1	123.5 (9)	N2—C11—C16	110.02 (8)
C1—N1—H1	126.2 (9)	C12—C11—C16	110.54 (8)
C10—N2—C11	122.51 (8)	N2—C11—H11	108.1
C10—N2—H2	116.5 (8)	C12—C11—H11	108.1
C11—N2—H2	120.8 (8)	C16—C11—H11	108.1
N1—C1—C2	129.11 (9)	C11—C12—C13	109.95 (8)
N1—C1—C6	107.90 (9)	C11—C12—H12A	109.7
C2—C1—C6	122.99 (9)	C13—C12—H12A	109.7
C3—C2—C1	117.30 (9)	C11—C12—H12B	109.7
C3—C2—H2A	121.3	C13—C12—H12B	109.7
C1—C2—H2A	121.3	H12A—C12—H12B	108.2
C2—C3—C4	119.17 (9)	C14—C13—C12	111.15 (9)
C2—C3—H3	120.4	C14—C13—H13A	109.4
C4—C3—H3	120.4	C12—C13—H13A	109.4
F1—C4—C5	118.04 (9)	C14—C13—H13B	109.4
F1—C4—C3	117.05 (9)	C12—C13—H13B	109.4
C5—C4—C3	124.91 (9)	H13A—C13—H13B	108.0
C4—C5—C6	116.40 (9)	C15—C14—C13	111.51 (8)
C4—C5—H5	121.8	C15—C14—H14A	109.3
C6—C5—H5	121.8	C13—C14—H14A	109.3
C5—C6—C1	119.23 (9)	C15—C14—H14B	109.3
C5—C6—C7	134.48 (9)	C13—C14—H14B	109.3
C1—C6—C7	106.27 (8)	H14A—C14—H14B	108.0
C8—C7—C9	127.81 (9)	C14—C15—C16	111.87 (8)
C8—C7—C6	106.20 (8)	C14—C15—H15A	109.2
C9—C7—C6	125.88 (8)	C16—C15—H15A	109.2
N1—C8—C7	110.23 (8)	C14—C15—H15B	109.2
N1—C8—H8	124.9	C16—C15—H15B	109.2
C7—C8—H8	124.9	H15A—C15—H15B	107.9
O1—C9—C7	123.40 (9)	C11—C16—C15	110.71 (8)
O1—C9—C10	117.35 (8)	C11—C16—H16A	109.5
C7—C9—C10	119.25 (8)	C15—C16—H16A	109.5
O2—C10—N2	124.75 (9)	C11—C16—H16B	109.5
O2—C10—C9	122.28 (8)	C15—C16—H16B	109.5
N2—C10—C9	112.97 (8)	H16A—C16—H16B	108.1

C8—N1—C1—C2	−178.59 (10)	C6—C7—C8—N1	1.51 (10)
C8—N1—C1—C6	0.56 (11)	C8—C7—C9—O1	−175.91 (9)
N1—C1—C2—C3	178.08 (9)	C6—C7—C9—O1	−0.28 (16)
C6—C1—C2—C3	−0.96 (14)	C8—C7—C9—C10	3.92 (15)
C1—C2—C3—C4	0.18 (14)	C6—C7—C9—C10	179.56 (8)
C2—C3—C4—F1	−179.24 (8)	C11—N2—C10—O2	2.07 (15)
C2—C3—C4—C5	0.59 (15)	C11—N2—C10—C9	−177.56 (8)
F1—C4—C5—C6	179.28 (8)	O1—C9—C10—O2	−168.77 (9)
C3—C4—C5—C6	−0.55 (15)	C7—C9—C10—O2	11.39 (14)
C4—C5—C6—C1	−0.23 (13)	O1—C9—C10—N2	10.87 (12)
C4—C5—C6—C7	−178.32 (10)	C7—C9—C10—N2	−168.98 (9)
N1—C1—C6—C5	−178.22 (8)	C10—N2—C11—C12	−68.08 (12)
C2—C1—C6—C5	1.00 (14)	C10—N2—C11—C16	168.70 (8)
N1—C1—C6—C7	0.37 (10)	N2—C11—C12—C13	178.16 (8)
C2—C1—C6—C7	179.58 (9)	C16—C11—C12—C13	−58.92 (11)
C5—C6—C7—C8	177.15 (10)	C11—C12—C13—C14	57.56 (12)
C1—C6—C7—C8	−1.12 (10)	C12—C13—C14—C15	−54.88 (12)
C5—C6—C7—C9	0.74 (17)	C13—C14—C15—C16	53.30 (12)
C1—C6—C7—C9	−177.53 (9)	N2—C11—C16—C15	−178.68 (8)
C1—N1—C8—C7	−1.32 (11)	C12—C11—C16—C15	57.37 (11)
C9—C7—C8—N1	177.83 (9)	C14—C15—C16—C11	−54.54 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1ⁱ	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1···O2ⁱⁱ	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8···O1ⁱⁱⁱ	0.95	2.31	3.0586 (12)	136

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇FN₂O₂
M_r	288.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	11.5065 (15), 9.7666 (12), 12.3139 (16)
β (°)	96.639 (5)
V (Å³)	1374.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.980, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18432, 3717, 3007
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.04
No. of reflections	3717
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1ⁱ	0.905 (13)	2.275 (13)	3.1234 (11)	156.1 (11)
N1—H1···O2ⁱⁱ	0.939 (14)	1.863 (14)	2.7786 (11)	164.5 (13)
C8—H8···O1ⁱⁱⁱ	0.95	2.31	3.0586 (12)	135.8

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Program of the Science Foundation of Tianjin (08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (09ZCKFSH01700).

References

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