3-Benzyl­amino-2-cyano-N-[N-(2-fluoro­phenyl)­carbamo­yl]-3-(methyl­sulfanyl)acryl­amide

Zhong, S.; Fan, M.; Liu, J.; Liu, B.

doi:10.1107/S1600536811046125

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3230

https://doi.org/10.1107/S1600536811046125

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3-Benzylamino-2-cyano-N-[N-(2-fluorophenyl)carbamoyl]-3-(methylsulfanyl)acrylamide

Shihua Zhong,^a Mingliang Fan,^a Jianbing Liu ^a ^* and Bingyu Liu ^a

^aCollege of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, Hunan, People's Republic of China
^*Correspondence e-mail: hunansdljb@163.com

(Received 12 September 2011; accepted 2 November 2011; online 9 November 2011)

In the crystal structure of the title compound, C₁₉H₁₇FN₄O₂S, molecules are linked via pairs of N—H⋯N interactions, forming centrosymmetric dimers. Two intramolecular N—H⋯O hydrogen bonds stabilize the molecular conformation.

Related literature

The title compound was synthesized as a herbicide. For details of the synthesis, see: Wang et al. (2004 ); Senda et al. (1972 ); Xue et al. (2002 ); Liu et al. (1998 ); Zhang et al. (2008 ).

Experimental

Crystal data

C₁₉H₁₇FN₄O₂S
M_r = 384.43
Triclinic, $[P \overline 1]$
a = 9.2415 (18) Å
b = 10.047 (2) Å
c = 11.0949 (19) Å
α = 73.312 (6)°
β = 66.880 (6)°
γ = 84.295 (7)°
V = 907.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 133 K
0.48 × 0.39 × 0.39 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.906, T_max = 0.923
8644 measured reflections
4089 independent reflections
3137 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.079
S = 1.00
4089 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.860 (17)	1.894 (17)	2.6024 (15)	138.7 (15)
N3—H3N⋯O1	0.827 (16)	1.912 (16)	2.6012 (16)	140.1 (14)
N2—H2N⋯N4ⁱ	0.858 (15)	2.229 (16)	3.0710 (17)	166.8 (14)
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2008 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811046125/ds2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046125/ds2144Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046125/ds2144Isup3.cml

checkCIF report

Related literature top

The title compound was synthesized as a herbicide. For details of the synthesis, see: Wang et al. (2004); Senda et al. (1972); Xue et al. (2002); Liu et al. (1998); Zhang et al. (2008).

Experimental top

The title compound was prepared according to the reported method (Wang et al., 2004; Senda et al., 1972). Crystals of (I) suitable for XRD were obtained by slow evaporation of the acetone solution at 293 K.

Structure description top

The title compound was synthesized as a herbicide. For details of the synthesis, see: Wang et al. (2004); Senda et al. (1972); Xue et al. (2002); Liu et al. (1998); Zhang et al. (2008).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound shows displacement ellipsoids drawn at the 50% probability level, all H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound with hydrogen bonds drawn as dashed lines.

3-Benzylamino-2-cyano-N-[N-(2- fluorophenyl)carbamoyl]-3-(methylsulfanyl)acrylamide top

Crystal data top

C₁₉H₁₇FN₄O₂S	Z = 2
M_r = 384.43	F(000) = 400
Triclinic, P1	D_x = 1.407 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2415 (18) Å	Cell parameters from 2908 reflections
b = 10.047 (2) Å	θ = 2.4–29.1°
c = 11.0949 (19) Å	µ = 0.21 mm⁻¹
α = 73.312 (6)°	T = 133 K
β = 66.880 (6)°	Block, colourless
γ = 84.295 (7)°	0.48 × 0.39 × 0.39 mm
V = 907.4 (3) Å³

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	4089 independent reflections
Radiation source: Rotating Anode	3137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
phi and ω scans	h = −11→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
T_min = 0.906, T_max = 0.923	l = −14→12
8644 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0296P)² + 0.119P] where P = (F_o² + 2F_c²)/3
4089 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₇FN₄O₂S	γ = 84.295 (7)°
M_r = 384.43	V = 907.4 (3) Å³
Triclinic, P1	Z = 2
a = 9.2415 (18) Å	Mo Kα radiation
b = 10.047 (2) Å	µ = 0.21 mm⁻¹
c = 11.0949 (19) Å	T = 133 K
α = 73.312 (6)°	0.48 × 0.39 × 0.39 mm
β = 66.880 (6)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	4089 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3137 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.923	R_int = 0.025
8644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.32 e Å⁻³
4089 reflections	Δρ_min = −0.23 e Å⁻³
251 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-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
S1	0.42534 (5)	0.14869 (4)	0.89857 (4)	0.02801 (11)
F1	0.21687 (11)	0.56288 (9)	0.25643 (8)	0.0357 (2)
O1	0.27259 (13)	0.42794 (11)	0.56187 (9)	0.0295 (3)
O2	−0.00916 (14)	0.75621 (12)	0.64645 (10)	0.0363 (3)
N1	0.43164 (14)	0.22266 (12)	0.65160 (11)	0.0222 (3)
N2	0.10887 (14)	0.55174 (12)	0.70402 (12)	0.0228 (3)
N3	0.11794 (15)	0.64303 (13)	0.48270 (12)	0.0239 (3)
N4	0.05563 (16)	0.35724 (14)	1.03305 (12)	0.0341 (3)
C1	0.63303 (18)	−0.12037 (16)	0.63660 (14)	0.0265 (3)
H1	0.7399	−0.0901	0.5950	0.032*
C2	0.5979 (2)	−0.26010 (17)	0.67324 (16)	0.0360 (4)
H2	0.6802	−0.3254	0.6567	0.043*
C3	0.4422 (2)	−0.30499 (17)	0.73435 (16)	0.0394 (4)
H3	0.4175	−0.4012	0.7596	0.047*
C4	0.3231 (2)	−0.20958 (17)	0.75847 (15)	0.0347 (4)
H4	0.2164	−0.2403	0.8006	0.042*
C5	0.35910 (18)	−0.06872 (16)	0.72123 (14)	0.0259 (3)
H5	0.2768	−0.0035	0.7382	0.031*
C6	0.51439 (16)	−0.02309 (14)	0.65956 (12)	0.0199 (3)
C7	0.56151 (16)	0.12821 (14)	0.61482 (14)	0.0223 (3)
H7A	0.6365	0.1390	0.6553	0.027*
H7B	0.6175	0.1559	0.5146	0.027*
C8	0.36183 (16)	0.25079 (14)	0.77143 (13)	0.0194 (3)
C9	0.24408 (17)	0.35141 (14)	0.79187 (13)	0.0219 (2)
C10	0.21072 (17)	0.44413 (15)	0.67827 (13)	0.0218 (3)
C11	0.06720 (17)	0.66004 (15)	0.60914 (14)	0.0235 (3)
C12	0.10494 (16)	0.73778 (15)	0.36651 (13)	0.0220 (3)
C13	0.05148 (17)	0.87350 (16)	0.35728 (15)	0.0287 (3)
H13	0.0137	0.9076	0.4355	0.034*
C14	0.05355 (18)	0.95894 (17)	0.23327 (16)	0.0354 (4)
H14	0.0189	1.0520	0.2271	0.042*
C15	0.10502 (19)	0.91076 (18)	0.11951 (16)	0.0378 (4)
H15	0.1044	0.9701	0.0359	0.045*
C16	0.15778 (19)	0.77617 (18)	0.12629 (15)	0.0330 (4)
H16	0.1927	0.7414	0.0485	0.040*
C17	0.15823 (17)	0.69412 (15)	0.24895 (14)	0.0259 (3)
C18	0.4107 (2)	0.25546 (18)	1.00866 (16)	0.0385 (4)
H18A	0.4372	0.3521	0.9544	0.058*
H18B	0.4839	0.2222	1.0548	0.058*
H18C	0.3030	0.2501	1.0767	0.058*
C19	0.14271 (17)	0.35427 (15)	0.92622 (13)	0.0219 (2)
H3N	0.1721 (19)	0.5738 (17)	0.4704 (15)	0.030 (5)*
H2N	0.0681 (19)	0.5644 (16)	0.7839 (16)	0.035 (5)*
H1N	0.394 (2)	0.2677 (18)	0.5923 (17)	0.040 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0371 (2)	0.0269 (2)	0.02340 (19)	0.00577 (17)	−0.01710 (17)	−0.00569 (15)
F1	0.0496 (6)	0.0324 (5)	0.0293 (5)	0.0090 (4)	−0.0187 (4)	−0.0121 (4)
O1	0.0418 (7)	0.0305 (6)	0.0189 (5)	0.0157 (5)	−0.0141 (5)	−0.0122 (4)
O2	0.0447 (7)	0.0339 (7)	0.0331 (6)	0.0205 (6)	−0.0174 (5)	−0.0163 (5)
N1	0.0279 (7)	0.0215 (7)	0.0191 (6)	0.0080 (5)	−0.0107 (5)	−0.0082 (5)
N2	0.0267 (7)	0.0248 (7)	0.0179 (6)	0.0071 (5)	−0.0086 (5)	−0.0096 (5)
N3	0.0289 (7)	0.0202 (7)	0.0236 (6)	0.0069 (6)	−0.0117 (5)	−0.0073 (5)
N4	0.0354 (8)	0.0392 (8)	0.0242 (7)	0.0105 (7)	−0.0087 (6)	−0.0108 (6)
C1	0.0287 (8)	0.0298 (8)	0.0253 (7)	0.0082 (7)	−0.0129 (7)	−0.0125 (6)
C2	0.0572 (12)	0.0292 (9)	0.0354 (9)	0.0155 (8)	−0.0299 (9)	−0.0166 (7)
C3	0.0736 (14)	0.0225 (9)	0.0310 (8)	−0.0057 (9)	−0.0287 (9)	−0.0059 (7)
C4	0.0418 (10)	0.0380 (10)	0.0239 (8)	−0.0138 (8)	−0.0074 (7)	−0.0103 (7)
C5	0.0257 (8)	0.0303 (8)	0.0232 (7)	0.0001 (7)	−0.0070 (6)	−0.0127 (6)
C6	0.0231 (7)	0.0241 (7)	0.0140 (6)	0.0031 (6)	−0.0079 (6)	−0.0075 (5)
C7	0.0190 (7)	0.0233 (8)	0.0216 (7)	0.0028 (6)	−0.0044 (6)	−0.0074 (6)
C8	0.0229 (7)	0.0182 (7)	0.0180 (6)	−0.0018 (6)	−0.0085 (6)	−0.0046 (5)
C9	0.0264 (5)	0.0216 (5)	0.0189 (5)	0.0030 (4)	−0.0093 (4)	−0.0073 (4)
C10	0.0241 (7)	0.0222 (7)	0.0206 (7)	0.0025 (6)	−0.0083 (6)	−0.0091 (6)
C11	0.0225 (8)	0.0234 (8)	0.0262 (7)	0.0028 (6)	−0.0108 (6)	−0.0078 (6)
C12	0.0182 (7)	0.0225 (8)	0.0243 (7)	−0.0019 (6)	−0.0099 (6)	−0.0016 (6)
C13	0.0227 (8)	0.0274 (8)	0.0339 (8)	0.0034 (6)	−0.0114 (7)	−0.0052 (6)
C14	0.0254 (8)	0.0298 (9)	0.0444 (9)	0.0018 (7)	−0.0160 (8)	0.0030 (7)
C15	0.0284 (9)	0.0434 (11)	0.0354 (9)	−0.0044 (8)	−0.0190 (8)	0.0098 (7)
C16	0.0303 (9)	0.0428 (10)	0.0262 (8)	−0.0024 (7)	−0.0146 (7)	−0.0034 (7)
C17	0.0242 (8)	0.0255 (8)	0.0291 (8)	0.0005 (6)	−0.0129 (7)	−0.0051 (6)
C18	0.0453 (10)	0.0519 (11)	0.0315 (8)	0.0081 (9)	−0.0240 (8)	−0.0198 (8)
C19	0.0264 (5)	0.0216 (5)	0.0189 (5)	0.0030 (4)	−0.0093 (4)	−0.0073 (4)

Geometric parameters (Å, º) top

S1—C8	1.7567 (13)	C4—H4	0.9500
S1—C18	1.8041 (15)	C5—C6	1.385 (2)
F1—C17	1.3674 (16)	C5—H5	0.9500
O1—C10	1.2424 (16)	C6—C7	1.5085 (19)
O2—C11	1.2115 (16)	C7—H7A	0.9900
N1—C8	1.3303 (17)	C7—H7B	0.9900
N1—C7	1.4556 (17)	C8—C9	1.4060 (18)
N1—H1N	0.860 (17)	C9—C19	1.4223 (19)
N2—C10	1.3785 (17)	C9—C10	1.4577 (18)
N2—C11	1.4204 (17)	C12—C17	1.3847 (19)
N2—H2N	0.858 (15)	C12—C13	1.393 (2)
N3—C11	1.3499 (18)	C13—C14	1.391 (2)
N3—C12	1.4059 (17)	C13—H13	0.9500
N3—H3N	0.827 (16)	C14—C15	1.374 (2)
N4—C19	1.1488 (17)	C14—H14	0.9500
C1—C2	1.379 (2)	C15—C16	1.382 (2)
C1—C6	1.3903 (19)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.375 (2)
C2—C3	1.386 (2)	C16—H16	0.9500
C2—H2	0.9500	C18—H18A	0.9800
C3—C4	1.382 (2)	C18—H18B	0.9800
C3—H3	0.9500	C18—H18C	0.9800
C4—C5	1.391 (2)

C8—S1—C18	106.50 (7)	C9—C8—S1	124.36 (10)
C8—N1—C7	126.66 (12)	C8—C9—C19	120.11 (12)
C8—N1—H1N	113.5 (11)	C8—C9—C10	121.33 (12)
C7—N1—H1N	119.8 (11)	C19—C9—C10	118.19 (12)
C10—N2—C11	127.92 (12)	O1—C10—N2	120.88 (12)
C10—N2—H2N	120.9 (11)	O1—C10—C9	121.44 (12)
C11—N2—H2N	110.9 (11)	N2—C10—C9	117.68 (12)
C11—N3—C12	127.09 (13)	O2—C11—N3	126.13 (13)
C11—N3—H3N	116.0 (11)	O2—C11—N2	119.24 (12)
C12—N3—H3N	116.4 (11)	N3—C11—N2	114.63 (12)
C2—C1—C6	121.00 (16)	C17—C12—C13	117.29 (13)
C2—C1—H1	119.5	C17—C12—N3	116.69 (13)
C6—C1—H1	119.5	C13—C12—N3	125.92 (13)
C1—C2—C3	119.78 (16)	C14—C13—C12	119.87 (14)
C1—C2—H2	120.1	C14—C13—H13	120.1
C3—C2—H2	120.1	C12—C13—H13	120.1
C4—C3—C2	119.85 (16)	C15—C14—C13	120.97 (16)
C4—C3—H3	120.1	C15—C14—H14	119.5
C2—C3—H3	120.1	C13—C14—H14	119.5
C3—C4—C5	120.16 (16)	C14—C15—C16	120.23 (14)
C3—C4—H4	119.9	C14—C15—H15	119.9
C5—C4—H4	119.9	C16—C15—H15	119.9
C6—C5—C4	120.29 (15)	C17—C16—C15	118.02 (15)
C6—C5—H5	119.9	C17—C16—H16	121.0
C4—C5—H5	119.9	C15—C16—H16	121.0
C5—C6—C1	118.91 (14)	F1—C17—C16	119.01 (13)
C5—C6—C7	122.99 (13)	F1—C17—C12	117.38 (12)
C1—C6—C7	118.09 (13)	C16—C17—C12	123.59 (14)
N1—C7—C6	114.88 (12)	S1—C18—H18A	109.5
N1—C7—H7A	108.5	S1—C18—H18B	109.5
C6—C7—H7A	108.5	H18A—C18—H18B	109.5
N1—C7—H7B	108.5	S1—C18—H18C	109.5
C6—C7—H7B	108.5	H18A—C18—H18C	109.5
H7A—C7—H7B	107.5	H18B—C18—H18C	109.5
N1—C8—C9	121.34 (12)	N4—C19—C9	177.14 (16)
N1—C8—S1	114.28 (10)

C6—C1—C2—C3	−0.2 (2)	C19—C9—C10—O1	−165.04 (14)
C1—C2—C3—C4	−0.1 (2)	C8—C9—C10—N2	−171.45 (13)
C2—C3—C4—C5	0.2 (2)	C19—C9—C10—N2	15.5 (2)
C3—C4—C5—C6	0.1 (2)	C12—N3—C11—O2	6.0 (3)
C4—C5—C6—C1	−0.5 (2)	C12—N3—C11—N2	−174.67 (13)
C4—C5—C6—C7	179.10 (12)	C10—N2—C11—O2	−170.90 (14)
C2—C1—C6—C5	0.52 (19)	C10—N2—C11—N3	9.7 (2)
C2—C1—C6—C7	−179.06 (12)	C11—N3—C12—C17	−176.54 (14)
C8—N1—C7—C6	81.84 (17)	C11—N3—C12—C13	7.2 (2)
C5—C6—C7—N1	4.96 (18)	C17—C12—C13—C14	−0.1 (2)
C1—C6—C7—N1	−175.49 (12)	N3—C12—C13—C14	176.14 (14)
C7—N1—C8—C9	175.63 (13)	C12—C13—C14—C15	1.2 (2)
C7—N1—C8—S1	−6.28 (19)	C13—C14—C15—C16	−0.8 (2)
C18—S1—C8—N1	148.59 (11)	C14—C15—C16—C17	−0.6 (2)
C18—S1—C8—C9	−33.39 (15)	C15—C16—C17—F1	−176.93 (14)
N1—C8—C9—C19	163.12 (14)	C15—C16—C17—C12	1.8 (2)
S1—C8—C9—C19	−14.8 (2)	C13—C12—C17—F1	177.34 (13)
N1—C8—C9—C10	−9.8 (2)	N3—C12—C17—F1	0.7 (2)
S1—C8—C9—C10	172.35 (11)	C13—C12—C17—C16	−1.4 (2)
C11—N2—C10—O1	−4.2 (2)	N3—C12—C17—C16	−178.01 (14)
C11—N2—C10—C9	175.25 (14)	C8—C9—C19—N4	−135 (3)
C8—C9—C10—O1	8.0 (2)	C10—C9—C19—N4	38 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.860 (17)	1.894 (17)	2.6024 (15)	138.7 (15)
N3—H3N···O1	0.827 (16)	1.912 (16)	2.6012 (16)	140.1 (14)
N2—H2N···N4ⁱ	0.858 (15)	2.229 (16)	3.0710 (17)	166.8 (14)

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇FN₄O₂S
M_r	384.43
Crystal system, space group	Triclinic, P1
Temperature (K)	133
a, b, c (Å)	9.2415 (18), 10.047 (2), 11.0949 (19)
α, β, γ (°)	73.312 (6), 66.880 (6), 84.295 (7)
V (Å³)	907.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.48 × 0.39 × 0.39

Data collection
Diffractometer	Rigaku AFC10/Saturn724+
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.906, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	8644, 4089, 3137
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.079, 1.00
No. of reflections	4089
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

Computer programs: CrystalClear (Rigaku, 2008), 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
N1—H1N···O1	0.860 (17)	1.894 (17)	2.6024 (15)	138.7 (15)
N3—H3N···O1	0.827 (16)	1.912 (16)	2.6012 (16)	140.1 (14)
N2—H2N···N4ⁱ	0.858 (15)	2.229 (16)	3.0710 (17)	166.8 (14)

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

We are grateful to Hunan Normal University for financial support.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Liu, H. Y., Sha, Y. L., Lu, R. J., Yang, H. Z. & Lai, L. H. (1998). Chin. Sci. Bull. 43, 397–401. Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Senda, S., Hirota, K. & Notani, J. (1972). Chem. Pharm. Bull. 20, 1380–1388. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Q. M., Li, H., Li, Y. G. & Huang, R. Q. (2004). J. Agric. Food Chem. 52, 1918–1922. Web of Science CrossRef PubMed CAS Google Scholar
Xue, Y., Wu, S. Z., Peng, A. D., Yang, Y. & Lu, S. W. (2002). Chin. J. Org. Chem. 22, 529–535. CAS Google Scholar
Zhang, H. P., Song, B. A., Wang, X. Y., Long, N., Hu, D. Y., Yang, S., Xue, W., Lu, P. & Jin, H. L. (2008). Chin. J. Org. Chem. 28, 17–28. Google Scholar

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Volume 67| Part 12| December 2011| Page o3230

https://doi.org/10.1107/S1600536811046125

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

3-Benzyl­amino-2-cyano-N-[N-(2-fluoro­phenyl)­carbamo­yl]-3-(methyl­sulfanyl)acryl­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Benzylamino-2-cyano-N-[N-(2-fluorophenyl)carbamoyl]-3-(methylsulfanyl)acrylamide