4-{2-[(Z)-(5-Methyl-2-fur-yl)methyl-idene-amino]-eth-yl}benzene-sulfonamide.

In the title compound, C(14)H(16)N(2)O(3)S, the dihedral angle between the phenyl and 5-methyl-furan groups is 54.89 (14)° and the C=N bond assumes a trans conformation. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) ring motifs. The dimers are inter-linked by N-H⋯N hydrogen bonds, resulting in the formation of infinite chains extending along the b axis. The packing is consolidated by weak C-H⋯π inter-actions.

Related literature

For biochemical background and related crystal structures, see: Chohan et al. (2008 ▶); Davis et al. (2007 ▶); Li (2006 ▶); Suo (2008 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H16N2O3S

M = 292.35

Triclinic,

a = 9.1947 (14) Å

b = 9.7592 (14) Å

c = 9.8493 (15) Å

α = 61.027 (6)°

β = 70.650 (6)°

γ = 81.574 (7)°

V = 729.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.20 × 0.16 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.956, T max = 0.977

10058 measured reflections

2638 independent reflections

1461 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.153

S = 0.97

2638 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034045/hb5617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034045/hb5617Isup2.hkl

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

C14H16N2O3S	Z = 2
Mr = 292.35	F(000) = 308
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1947 (14) Å	Cell parameters from 1461 reflections
b = 9.7592 (14) Å	θ = 2.4–25.3°
c = 9.8493 (15) Å	µ = 0.23 mm−1
α = 61.027 (6)°	T = 296 K
β = 70.650 (6)°	Plate, dark yellow
γ = 81.574 (7)°	0.20 × 0.16 × 0.08 mm
V = 729.4 (2) Å3

Bruker Kappa APEXII CCD diffractometer	2638 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
graphite	Rint = 0.068
Detector resolution: 8.20 pixels mm-1	θmax = 25.5°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.956, Tmax = 0.977	l = −11→11
10058 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0756P)2] where P = (Fo2 + 2Fc2)/3
2638 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.74690 (11)	0.53303 (11)	0.83986 (11)	0.0552 (4)
O1	0.6857 (3)	0.4598 (3)	1.0147 (3)	0.0670 (10)
O2	0.8947 (3)	0.6089 (3)	0.7640 (3)	0.0748 (11)
O3	0.7176 (3)	−0.2510 (3)	0.3423 (3)	0.0507 (8)
N1	0.6254 (4)	0.6587 (4)	0.7715 (4)	0.0646 (12)
N2	0.7059 (3)	−0.0369 (3)	0.4601 (4)	0.0574 (11)
C1	0.7622 (4)	0.1521 (4)	0.6961 (4)	0.0461 (11)
C2	0.8939 (4)	0.2404 (4)	0.6471 (4)	0.0510 (12)
C3	0.8887 (4)	0.3549 (4)	0.6906 (4)	0.0474 (11)
C4	0.7533 (4)	0.3868 (4)	0.7848 (4)	0.0413 (11)
C5	0.6216 (4)	0.2987 (4)	0.8352 (4)	0.0486 (12)
C6	0.6275 (4)	0.1842 (4)	0.7922 (4)	0.0510 (12)
C7	0.7667 (4)	0.0281 (4)	0.6470 (5)	0.0635 (14)
C8	0.7022 (5)	0.0834 (4)	0.5068 (5)	0.0725 (18)
C9	0.7504 (4)	0.0059 (4)	0.3090 (5)	0.0568 (14)
C10	0.7612 (4)	−0.0949 (4)	0.2409 (4)	0.0496 (12)
C11	0.8112 (4)	−0.0715 (5)	0.0851 (4)	0.0594 (16)
C12	0.8012 (4)	−0.2149 (5)	0.0879 (4)	0.0615 (16)
C13	0.7442 (4)	−0.3207 (4)	0.2452 (4)	0.0504 (12)
C14	0.7067 (5)	−0.4902 (4)	0.3273 (5)	0.0703 (16)
H1A	0.535 (4)	0.638 (5)	0.802 (5)	0.0777*
H1B	0.643 (4)	0.724 (5)	0.676 (5)	0.0777*
H2	0.98644	0.22087	0.58379	0.0612*
H3	0.97774	0.41220	0.65631	0.0567*
H5	0.52913	0.31836	0.89844	0.0585*
H6	0.53869	0.12590	0.82844	0.0611*
H7A	0.70791	−0.06283	0.73939	0.0768*
H7B	0.87257	−0.00344	0.61620	0.0768*
H8A	0.59655	0.11552	0.53728	0.0866*
H8B	0.76142	0.17392	0.41410	0.0866*
H9	0.77791	0.11076	0.23804	0.0682*
H11	0.84604	0.02315	−0.00750	0.0717*
H12	0.82872	−0.23341	−0.00147	0.0735*
H14A	0.74691	−0.53007	0.25033	0.1053*
H14B	0.59683	−0.50553	0.37049	0.1053*
H14C	0.75202	−0.54468	0.41435	0.1053*

	U11	U22	U33	U12	U13	U23
S1	0.0661 (7)	0.0559 (6)	0.0413 (6)	−0.0178 (5)	−0.0026 (4)	−0.0246 (5)
O1	0.0882 (19)	0.0783 (18)	0.0346 (14)	−0.0201 (14)	−0.0061 (13)	−0.0285 (13)
O2	0.0692 (17)	0.0801 (19)	0.0763 (19)	−0.0301 (14)	−0.0002 (14)	−0.0428 (16)
O3	0.0698 (16)	0.0453 (14)	0.0336 (13)	−0.0044 (11)	−0.0145 (11)	−0.0152 (11)
N1	0.073 (2)	0.050 (2)	0.052 (2)	−0.0051 (18)	−0.004 (2)	−0.0174 (16)
N2	0.081 (2)	0.0476 (18)	0.046 (2)	0.0008 (15)	−0.0207 (16)	−0.0225 (16)
C1	0.064 (2)	0.0387 (19)	0.038 (2)	0.0061 (17)	−0.0210 (18)	−0.0175 (16)
C2	0.058 (2)	0.053 (2)	0.034 (2)	0.0076 (18)	−0.0114 (17)	−0.0176 (18)
C3	0.053 (2)	0.047 (2)	0.0345 (19)	−0.0092 (16)	−0.0091 (16)	−0.0132 (17)
C4	0.044 (2)	0.0443 (19)	0.0272 (17)	−0.0032 (15)	−0.0060 (15)	−0.0124 (15)
C5	0.048 (2)	0.050 (2)	0.046 (2)	−0.0018 (16)	−0.0060 (16)	−0.0255 (18)
C6	0.052 (2)	0.049 (2)	0.050 (2)	−0.0070 (16)	−0.0112 (18)	−0.0221 (19)
C7	0.089 (3)	0.052 (2)	0.060 (2)	0.009 (2)	−0.032 (2)	−0.030 (2)
C8	0.118 (4)	0.049 (2)	0.064 (3)	0.008 (2)	−0.042 (2)	−0.029 (2)
C9	0.073 (3)	0.042 (2)	0.052 (2)	−0.0064 (18)	−0.025 (2)	−0.0135 (19)
C10	0.060 (2)	0.043 (2)	0.037 (2)	−0.0075 (16)	−0.0156 (16)	−0.0092 (17)
C11	0.069 (3)	0.062 (3)	0.031 (2)	−0.0100 (19)	−0.0118 (17)	−0.0085 (18)
C12	0.070 (3)	0.078 (3)	0.038 (2)	0.000 (2)	−0.0145 (18)	−0.029 (2)
C13	0.061 (2)	0.055 (2)	0.046 (2)	0.0056 (17)	−0.0223 (18)	−0.029 (2)
C14	0.105 (3)	0.054 (2)	0.062 (3)	0.004 (2)	−0.040 (2)	−0.026 (2)

S1—O1	1.441 (3)	C10—C11	1.357 (5)
S1—O2	1.428 (3)	C11—C12	1.402 (7)
S1—N1	1.582 (4)	C12—C13	1.346 (5)
S1—C4	1.743 (4)	C13—C14	1.482 (6)
O3—C10	1.385 (5)	C2—H2	0.9300
O3—C13	1.365 (5)	C3—H3	0.9300
N2—C8	1.446 (6)	C5—H5	0.9300
N2—C9	1.265 (5)	C6—H6	0.9300
N1—H1B	0.82 (4)	C7—H7A	0.9700
N1—H1A	0.80 (4)	C7—H7B	0.9700
C1—C6	1.387 (5)	C8—H8A	0.9700
C1—C7	1.496 (6)	C8—H8B	0.9700
C1—C2	1.399 (6)	C9—H9	0.9300
C2—C3	1.367 (6)	C11—H11	0.9300
C3—C4	1.382 (5)	C12—H12	0.9300
C4—C5	1.395 (6)	C14—H14A	0.9600
C5—C6	1.363 (6)	C14—H14B	0.9600
C7—C8	1.509 (6)	C14—H14C	0.9600
C9—C10	1.412 (6)
O1—S1—O2	118.85 (17)	C12—C13—C14	132.9 (4)
O1—S1—N1	106.50 (18)	C1—C2—H2	119.00
O1—S1—C4	106.27 (18)	C3—C2—H2	120.00
O2—S1—N1	107.94 (19)	C2—C3—H3	119.00
O2—S1—C4	108.41 (19)	C4—C3—H3	119.00
N1—S1—C4	108.5 (2)	C4—C5—H5	120.00
C10—O3—C13	107.0 (3)	C6—C5—H5	120.00
C8—N2—C9	116.4 (4)	C1—C6—H6	119.00
S1—N1—H1B	123 (3)	C5—C6—H6	119.00
H1A—N1—H1B	105 (4)	C1—C7—H7A	109.00
S1—N1—H1A	122 (3)	C1—C7—H7B	109.00
C6—C1—C7	121.5 (4)	C8—C7—H7A	109.00
C2—C1—C6	117.2 (4)	C8—C7—H7B	109.00
C2—C1—C7	121.3 (3)	H7A—C7—H7B	108.00
C1—C2—C3	121.1 (4)	N2—C8—H8A	109.00
C2—C3—C4	121.1 (4)	N2—C8—H8B	109.00
S1—C4—C3	121.0 (3)	C7—C8—H8A	109.00
C3—C4—C5	118.3 (4)	C7—C8—H8B	109.00
S1—C4—C5	120.7 (3)	H8A—C8—H8B	108.00
C4—C5—C6	120.4 (4)	N2—C9—H9	118.00
C1—C6—C5	121.9 (4)	C10—C9—H9	118.00
C1—C7—C8	112.3 (4)	C10—C11—H11	126.00
N2—C8—C7	112.2 (4)	C12—C11—H11	126.00
N2—C9—C10	124.4 (4)	C11—C12—H12	127.00
O3—C10—C9	119.6 (3)	C13—C12—H12	127.00
O3—C10—C11	108.0 (4)	C13—C14—H14A	109.00
C9—C10—C11	132.4 (4)	C13—C14—H14B	109.00
C10—C11—C12	108.2 (3)	C13—C14—H14C	109.00
C11—C12—C13	106.7 (4)	H14A—C14—H14B	110.00
O3—C13—C12	110.1 (4)	H14A—C14—H14C	110.00
O3—C13—C14	117.0 (3)	H14B—C14—H14C	109.00
O1—S1—C4—C3	−125.4 (3)	C2—C1—C7—C8	−100.7 (4)
O1—S1—C4—C5	54.5 (3)	C6—C1—C7—C8	79.4 (5)
O2—S1—C4—C3	3.4 (4)	C1—C2—C3—C4	0.2 (5)
O2—S1—C4—C5	−176.7 (3)	C2—C3—C4—S1	−179.9 (3)
N1—S1—C4—C3	120.4 (3)	C2—C3—C4—C5	0.2 (5)
N1—S1—C4—C5	−59.7 (3)	S1—C4—C5—C6	−179.8 (3)
C13—O3—C10—C9	−178.2 (4)	C3—C4—C5—C6	0.1 (5)
C13—O3—C10—C11	0.8 (4)	C4—C5—C6—C1	−0.9 (6)
C10—O3—C13—C12	−0.5 (4)	C1—C7—C8—N2	−179.7 (3)
C10—O3—C13—C14	179.7 (4)	N2—C9—C10—O3	1.7 (6)
C9—N2—C8—C7	−136.6 (4)	N2—C9—C10—C11	−177.1 (4)
C8—N2—C9—C10	−179.9 (4)	O3—C10—C11—C12	−0.8 (5)
C6—C1—C2—C3	−0.9 (5)	C9—C10—C11—C12	178.0 (4)
C7—C1—C2—C3	179.2 (3)	C10—C11—C12—C13	0.5 (5)
C2—C1—C6—C5	1.3 (5)	C11—C12—C13—O3	0.0 (5)
C7—C1—C6—C5	−178.8 (3)	C11—C12—C13—C14	179.8 (4)

Cg1 and Cg2 are the centroids of furan (C10—C13/O3) and phenyl (C1—C6) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.80 (4)	2.18 (4)	2.928 (5)	155 (4)
N1—H1B···N2ii	0.82 (4)	2.25 (5)	3.015 (5)	156 (5)
C6—H6···Cg1iii	0.93	2.87	3.596 (4)	136
C11—H11···Cg2iv	0.93	2.75	3.535 (4)	143
C14—H14C···Cg2v	0.96	2.84	3.743 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of furan (C10—C13/O3) and phenyl (C1—C6) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.80 (4)	2.18 (4)	2.928 (5)	155 (4)
N1—H1B⋯N2ii	0.82 (4)	2.25 (5)	3.015 (5)	156 (5)
C6—H6⋯Cg1iii	0.93	2.87	3.596 (4)	136
C11—H11⋯Cg2iv	0.93	2.75	3.535 (4)	143
C14—H14C⋯Cg2v	0.96	2.84	3.743 (5)	157

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