Crystal structure of (E)-N'-(3,4-di-fluoro-benzyl-idene)-4-methyl-benzene-sulfono-hydrazide.

In the title compound, C14H12F2N2O2S, the dihedral angle between the aromatic rings is 70.23 (8)° and the S-N-N=C torsion angle is 172.11 (11)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into [100] C(4) chains, with adjacent mol-ecules in the chain related by translational symmetry. The chains are linked by weak C-H⋯F and C-H⋯O inter-actions, thereby forming a three-dimensional network.

Related literature

For the biological activities of sulfonamides and sulfonyl­hydrazones, see: El-Sayed et al. (2011 ▸); de Oliveira et al. (2011 ▸); Zhao et al. (2011 ▸).

Experimental

Crystal data

C14H12F2N2O2S

M = 310.32

Monoclinic,

a = 5.3161 (11) Å

b = 15.388 (3) Å

c = 17.293 (4) Å

β = 97.44 (3)°

V = 1402.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ▸) T min = 0.950, T max = 0.970

14131 measured reflections

3328 independent reflections

2729 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.04

3328 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▸); 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015016205/hb7491sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016205/hb7491Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016205/hb7491Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016205/hb7491fig1.tif

Displacement ellipsoid plot (50% probability level) of the title compound.

CCDC reference: 1040450

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H12F2N2O2S	Dx = 1.469 Mg m−3
Mr = 310.32	Melting point: 426 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.3161 (11) Å	Cell parameters from 3967 reflections
b = 15.388 (3) Å	θ = 1.8–27.9°
c = 17.293 (4) Å	µ = 0.26 mm−1
β = 97.44 (3)°	T = 173 K
V = 1402.8 (5) Å3	Prism, colourless
Z = 4	0.20 × 0.18 × 0.12 mm
F(000) = 640

Rigaku Saturn diffractometer	3328 independent reflections
Radiation source: rotating anode	2729 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.047
ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	h = −6→6
Tmin = 0.950, Tmax = 0.970	k = −20→19
14131 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0715P)2 + 0.0398P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3328 reflections	Δρmax = 0.27 e Å−3
196 parameters	Δρmin = −0.39 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.057 (4)

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.

	x	y	z	Uiso*/Ueq
S1	0.17639 (7)	0.83591 (2)	0.34262 (2)	0.02258 (15)
F1	0.15725 (18)	0.45775 (6)	0.58632 (6)	0.0354 (3)
F2	0.52921 (19)	0.43477 (7)	0.70237 (6)	0.0403 (3)
O1	−0.0478 (2)	0.83384 (7)	0.38043 (6)	0.0300 (3)
O2	0.2561 (2)	0.91533 (7)	0.31005 (6)	0.0308 (3)
N1	0.3852 (2)	0.73655 (8)	0.45229 (7)	0.0243 (3)
N2	0.4159 (2)	0.81054 (9)	0.40836 (7)	0.0254 (3)
C1	0.3568 (3)	0.58214 (10)	0.54189 (9)	0.0245 (3)
H1	0.2203	0.5908	0.5014	0.029*
C2	0.3516 (3)	0.51491 (10)	0.59364 (9)	0.0245 (3)
C3	0.5465 (3)	0.50210 (10)	0.65353 (9)	0.0268 (3)
C4	0.7535 (3)	0.55625 (10)	0.66269 (9)	0.0286 (3)
H4	0.8868	0.5476	0.7042	0.034*
C5	0.7641 (3)	0.62404 (10)	0.60986 (9)	0.0257 (3)
H5	0.9075	0.6614	0.6148	0.031*
C6	0.5666 (3)	0.63768 (9)	0.54969 (8)	0.0218 (3)
C7	0.5820 (3)	0.71137 (10)	0.49678 (8)	0.0233 (3)
H7	0.7391	0.7405	0.4956	0.028*
C8	0.1461 (3)	0.75599 (9)	0.26968 (8)	0.0224 (3)
C9	0.3114 (3)	0.75831 (10)	0.21365 (9)	0.0274 (3)
H9	0.4410	0.8011	0.2162	0.033*
C10	0.2849 (3)	0.69783 (11)	0.15446 (9)	0.0323 (4)
H10	0.3983	0.6992	0.1163	0.039*
C11	0.0951 (4)	0.63458 (10)	0.14931 (10)	0.0331 (4)
C12	−0.0658 (3)	0.63306 (11)	0.20640 (10)	0.0315 (4)
H12	−0.1949	0.5901	0.2041	0.038*
C13	−0.0418 (3)	0.69311 (10)	0.26667 (9)	0.0270 (3)
H13	−0.1528	0.6912	0.3055	0.032*
C14	0.0698 (5)	0.56939 (13)	0.08375 (12)	0.0565 (6)
H14A	0.1822	0.5199	0.0982	0.085*
H14B	0.1170	0.5968	0.0365	0.085*
H14C	−0.1062	0.5491	0.0739	0.085*
H2	0.573 (2)	0.8215 (12)	0.3993 (12)	0.043 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0188 (2)	0.0234 (2)	0.0255 (2)	0.00121 (13)	0.00278 (14)	0.00296 (13)
F1	0.0271 (5)	0.0342 (6)	0.0442 (6)	−0.0066 (4)	0.0022 (4)	0.0015 (4)
F2	0.0390 (6)	0.0407 (6)	0.0410 (6)	0.0035 (4)	0.0041 (5)	0.0171 (4)
O1	0.0187 (6)	0.0373 (7)	0.0352 (6)	0.0019 (4)	0.0076 (5)	−0.0028 (5)
O2	0.0332 (7)	0.0237 (6)	0.0354 (6)	−0.0007 (5)	0.0037 (5)	0.0055 (4)
N1	0.0255 (7)	0.0257 (6)	0.0219 (6)	0.0010 (5)	0.0036 (5)	0.0019 (5)
N2	0.0179 (7)	0.0307 (7)	0.0274 (7)	−0.0027 (5)	0.0021 (5)	0.0064 (5)
C1	0.0213 (8)	0.0289 (8)	0.0226 (7)	0.0036 (6)	−0.0003 (6)	−0.0028 (6)
C2	0.0194 (8)	0.0261 (8)	0.0288 (8)	−0.0010 (6)	0.0054 (6)	−0.0034 (6)
C3	0.0288 (8)	0.0275 (8)	0.0250 (7)	0.0057 (6)	0.0068 (6)	0.0033 (6)
C4	0.0246 (8)	0.0355 (9)	0.0247 (7)	0.0060 (6)	−0.0013 (6)	0.0008 (6)
C5	0.0186 (7)	0.0305 (8)	0.0272 (7)	0.0005 (6)	0.0005 (6)	−0.0031 (6)
C6	0.0198 (8)	0.0255 (7)	0.0203 (7)	0.0041 (6)	0.0030 (6)	−0.0032 (5)
C7	0.0202 (8)	0.0283 (8)	0.0217 (7)	−0.0001 (6)	0.0036 (6)	−0.0022 (6)
C8	0.0204 (8)	0.0237 (7)	0.0228 (7)	0.0030 (6)	0.0010 (6)	0.0053 (5)
C9	0.0262 (9)	0.0268 (8)	0.0303 (8)	−0.0011 (6)	0.0075 (6)	0.0064 (6)
C10	0.0424 (10)	0.0314 (9)	0.0253 (8)	0.0008 (7)	0.0126 (7)	0.0057 (6)
C11	0.0471 (11)	0.0255 (8)	0.0263 (8)	0.0016 (7)	0.0036 (7)	0.0040 (6)
C12	0.0333 (9)	0.0257 (8)	0.0350 (9)	−0.0049 (7)	0.0028 (7)	0.0017 (6)
C13	0.0228 (8)	0.0281 (8)	0.0310 (8)	−0.0020 (6)	0.0067 (6)	0.0041 (6)
C14	0.0924 (18)	0.0407 (11)	0.0384 (11)	−0.0107 (11)	0.0163 (11)	−0.0076 (8)

S1—O1	1.4319 (12)	C5—H5	0.9500
S1—O2	1.4324 (11)	C6—C7	1.466 (2)
S1—N2	1.6404 (14)	C7—H7	0.9500
S1—C8	1.7542 (15)	C8—C13	1.387 (2)
F1—C2	1.3502 (18)	C8—C9	1.390 (2)
F2—C3	1.3473 (18)	C9—C10	1.377 (2)
N1—C7	1.2762 (19)	C9—H9	0.9500
N1—N2	1.3901 (17)	C10—C11	1.396 (3)
N2—H2	0.888 (9)	C10—H10	0.9500
C1—C2	1.371 (2)	C11—C12	1.388 (2)
C1—C6	1.398 (2)	C11—C14	1.507 (2)
C1—H1	0.9500	C12—C13	1.386 (2)
C2—C3	1.381 (2)	C12—H12	0.9500
C3—C4	1.373 (2)	C13—H13	0.9500
C4—C5	1.393 (2)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C6	1.395 (2)	C14—H14C	0.9800
O1—S1—O2	120.29 (6)	N1—C7—C6	120.22 (13)
O1—S1—N2	107.18 (7)	N1—C7—H7	119.9
O2—S1—N2	103.48 (7)	C6—C7—H7	119.9
O1—S1—C8	107.96 (7)	C13—C8—C9	120.60 (14)
O2—S1—C8	108.65 (7)	C13—C8—S1	120.99 (12)
N2—S1—C8	108.80 (7)	C9—C8—S1	118.40 (11)
C7—N1—N2	115.66 (12)	C10—C9—C8	119.19 (14)
N1—N2—S1	115.99 (10)	C10—C9—H9	120.4
N1—N2—H2	115.6 (13)	C8—C9—H9	120.4
S1—N2—H2	119.9 (13)	C9—C10—C11	121.46 (15)
C2—C1—C6	118.81 (14)	C9—C10—H10	119.3
C2—C1—H1	120.6	C11—C10—H10	119.3
C6—C1—H1	120.6	C12—C11—C10	118.25 (15)
F1—C2—C1	120.70 (14)	C12—C11—C14	121.39 (16)
F1—C2—C3	117.91 (14)	C10—C11—C14	120.36 (16)
C1—C2—C3	121.38 (14)	C13—C12—C11	121.22 (15)
F2—C3—C4	120.86 (14)	C13—C12—H12	119.4
F2—C3—C2	118.32 (14)	C11—C12—H12	119.4
C4—C3—C2	120.81 (14)	C12—C13—C8	119.28 (14)
C3—C4—C5	118.60 (14)	C12—C13—H13	120.4
C3—C4—H4	120.7	C8—C13—H13	120.4
C5—C4—H4	120.7	C11—C14—H14A	109.5
C4—C5—C6	120.77 (14)	C11—C14—H14B	109.5
C4—C5—H5	119.6	H14A—C14—H14B	109.5
C6—C5—H5	119.6	C11—C14—H14C	109.5
C5—C6—C1	119.61 (14)	H14A—C14—H14C	109.5
C5—C6—C7	118.97 (13)	H14B—C14—H14C	109.5
C1—C6—C7	121.40 (13)
C7—N1—N2—S1	172.11 (11)	C5—C6—C7—N1	−165.16 (14)
O1—S1—N2—N1	49.24 (12)	C1—C6—C7—N1	13.7 (2)
O2—S1—N2—N1	177.34 (10)	O1—S1—C8—C13	−12.85 (14)
C8—S1—N2—N1	−67.26 (12)	O2—S1—C8—C13	−144.84 (13)
C6—C1—C2—F1	−177.38 (13)	N2—S1—C8—C13	103.15 (13)
C6—C1—C2—C3	1.0 (2)	O1—S1—C8—C9	165.65 (11)
F1—C2—C3—F2	−1.6 (2)	O2—S1—C8—C9	33.66 (13)
C1—C2—C3—F2	179.95 (13)	N2—S1—C8—C9	−78.36 (13)
F1—C2—C3—C4	177.91 (14)	C13—C8—C9—C10	0.6 (2)
C1—C2—C3—C4	−0.5 (2)	S1—C8—C9—C10	−177.85 (12)
F2—C3—C4—C5	178.96 (13)	C8—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	−0.5 (2)	C9—C10—C11—C12	−1.0 (3)
C3—C4—C5—C6	1.1 (2)	C9—C10—C11—C14	179.77 (16)
C4—C5—C6—C1	−0.6 (2)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C7	178.21 (13)	C14—C11—C12—C13	179.94 (17)
C2—C1—C6—C5	−0.4 (2)	C11—C12—C13—C8	0.2 (2)
C2—C1—C6—C7	−179.24 (13)	C9—C8—C13—C12	−0.9 (2)
N2—N1—C7—C6	175.73 (11)	S1—C8—C13—C12	177.54 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	2.09 (1)	2.9747 (18)	174 (2)
C1—H1···F1ii	0.95	2.47	3.345 (2)	153
C4—H4···O2iii	0.95	2.57	3.473 (2)	159

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2O1i	0.89(1)	2.09(1)	2.9747(18)	174(2)
C1H1F1ii	0.95	2.47	3.345(2)	153
C4H4O2iii	0.95	2.57	3.473(2)	159

Symmetry codes: (i) ; (ii) ; (iii) .