N-Ethyl-N-phenyl-N'-tosyl-formamidine.

The title compound, C(16)H(18)N(2)O(2)S, was obtained as an unexpected product while attempting to form carbon-nitro-gen bonds by catalytic amidation. The mol-ecule displays an E conformation about the C=N double bond. The planes of the two aromatic rings in the mol-ecule form a dihedral angle of 47.06 (9)°.

Related literature

For the crystal structures of related compounds, see: Cole et al. (2005 ▶, 2007 ▶). For the synthesis of substituted sulfanilamides by catalytic amidation, see: Liu et al. (2008 ▶); Xu et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C16H18N2O2S

M = 302.38

Monoclinic,

a = 16.306 (5) Å

b = 8.122 (4) Å

c = 12.674 (4) Å

β = 108.22 (2)°

V = 1594.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 291 K

0.60 × 0.46 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: spherical (WinGX; Farrugia, 1999 ▶) T min = 0.885, T max = 0.918

3769 measured reflections

2928 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.005

3 standard reflections every 200 reflections intensity decay: 2.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.09

2928 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.44 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021953/rz2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021953/rz2331Isup2.hkl

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

C16H18N2O2S	F(000) = 640
Mr = 302.38	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.306 (5) Å	θ = 4.7–7.7°
b = 8.122 (4) Å	µ = 0.21 mm−1
c = 12.674 (4) Å	T = 291 K
β = 108.22 (2)°	Block, colourless
V = 1594.3 (10) Å3	0.60 × 0.46 × 0.42 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1958 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.005
graphite	θmax = 25.5°, θmin = 1.3°
ω–2θ scans	h = −6→19
Absorption correction: for a sphere (WinGX; Farrugia, 1999)	k = −9→0
Tmin = 0.885, Tmax = 0.918	l = −15→14
3769 measured reflections	3 standard reflections every 200 reflections
2928 independent reflections	intensity decay: 2.7%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0973P)2] where P = (Fo2 + 2Fc2)/3
2928 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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	0.22480 (4)	0.35989 (7)	0.03686 (5)	0.0502 (2)
O1	0.29488 (10)	0.4299 (2)	0.00582 (16)	0.0589 (5)
O2	0.20033 (12)	0.4417 (2)	0.12215 (16)	0.0671 (5)
N1	0.24137 (12)	0.1667 (2)	0.07283 (17)	0.0519 (5)
N2	0.33809 (12)	−0.0487 (2)	0.10219 (16)	0.0499 (5)
C1	−0.0882 (2)	0.3571 (5)	−0.3731 (3)	0.1032 (13)
H1A	−0.1362	0.4031	−0.3547	0.155*
H1B	−0.1020	0.2469	−0.4003	0.155*
H1C	−0.0763	0.4232	−0.4294	0.155*
C2	−0.00939 (19)	0.3541 (4)	−0.2704 (3)	0.0693 (8)
C3	−0.01841 (18)	0.3645 (4)	−0.1664 (3)	0.0808 (9)
H3	−0.0734	0.3725	−0.1595	0.097*
C4	0.05244 (17)	0.3632 (4)	−0.0724 (3)	0.0706 (8)
H4	0.0452	0.3694	−0.0026	0.085*
C5	0.13384 (15)	0.3529 (3)	−0.0822 (2)	0.0488 (6)
C6	0.14362 (18)	0.3421 (4)	−0.1855 (3)	0.0739 (8)
H6	0.1985	0.3331	−0.1928	0.089*
C7	0.0719 (2)	0.3447 (5)	−0.2784 (3)	0.0844 (10)
H7	0.0791	0.3399	−0.3483	0.101*
C8	0.31639 (14)	0.1071 (3)	0.07690 (19)	0.0465 (5)
H8	0.3564	0.1767	0.0614	0.056*
C9	0.27942 (17)	−0.1647 (3)	0.1310 (3)	0.0654 (8)
H9A	0.2849	−0.2722	0.1006	0.078*
H9B	0.2203	−0.1278	0.0979	0.078*
C10	0.2990 (2)	−0.1785 (4)	0.2552 (3)	0.0852 (9)
H10A	0.3586	−0.2073	0.2887	0.128*
H10B	0.2631	−0.2620	0.2716	0.128*
H10C	0.2877	−0.0749	0.2844	0.128*
C11	0.42519 (15)	−0.1012 (3)	0.11568 (19)	0.0459 (6)
C12	0.49282 (16)	−0.0216 (3)	0.1901 (2)	0.0597 (7)
H12	0.4828	0.0657	0.2320	0.072*
C13	0.57586 (17)	−0.0723 (4)	0.2023 (3)	0.0689 (8)
H13	0.6220	−0.0188	0.2529	0.083*
C14	0.59129 (19)	−0.1996 (4)	0.1413 (3)	0.0700 (8)
H14	0.6477	−0.2328	0.1505	0.084*
C15	0.5245 (2)	−0.2778 (4)	0.0673 (3)	0.0753 (9)
H15	0.5352	−0.3637	0.0249	0.090*
C16	0.44046 (19)	−0.2311 (3)	0.0543 (2)	0.0611 (7)
H16	0.3946	−0.2867	0.0047	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0381 (3)	0.0471 (4)	0.0608 (4)	0.0024 (2)	0.0089 (3)	−0.0001 (3)
O1	0.0414 (9)	0.0505 (9)	0.0797 (12)	−0.0026 (7)	0.0118 (9)	0.0065 (9)
O2	0.0571 (11)	0.0710 (12)	0.0682 (12)	0.0060 (9)	0.0124 (9)	−0.0151 (10)
N1	0.0370 (10)	0.0499 (11)	0.0639 (13)	0.0017 (8)	0.0084 (9)	0.0074 (9)
N2	0.0409 (11)	0.0454 (11)	0.0538 (12)	0.0006 (8)	0.0010 (9)	0.0040 (9)
C1	0.067 (2)	0.126 (3)	0.089 (2)	0.013 (2)	−0.0152 (19)	−0.004 (2)
C2	0.0511 (15)	0.0738 (18)	0.0694 (19)	0.0089 (13)	−0.0011 (14)	−0.0040 (15)
C3	0.0391 (14)	0.114 (3)	0.084 (2)	0.0170 (16)	0.0112 (15)	0.0069 (18)
C4	0.0431 (14)	0.099 (2)	0.0668 (17)	0.0185 (14)	0.0139 (13)	0.0050 (16)
C5	0.0368 (12)	0.0470 (12)	0.0596 (15)	0.0059 (10)	0.0108 (11)	0.0012 (11)
C6	0.0446 (15)	0.107 (2)	0.0693 (19)	0.0033 (15)	0.0162 (14)	−0.0107 (17)
C7	0.0657 (19)	0.125 (3)	0.0575 (18)	0.0086 (19)	0.0119 (16)	−0.0106 (18)
C8	0.0403 (12)	0.0481 (13)	0.0452 (13)	−0.0006 (10)	0.0047 (10)	0.0019 (10)
C9	0.0468 (14)	0.0541 (14)	0.083 (2)	−0.0065 (11)	0.0022 (14)	0.0118 (14)
C10	0.092 (2)	0.082 (2)	0.091 (2)	−0.0002 (18)	0.042 (2)	0.0094 (19)
C11	0.0457 (13)	0.0448 (12)	0.0417 (12)	0.0060 (10)	0.0058 (10)	0.0057 (10)
C12	0.0460 (13)	0.0597 (15)	0.0631 (16)	0.0036 (12)	0.0022 (12)	−0.0096 (12)
C13	0.0440 (14)	0.0769 (18)	0.0763 (19)	0.0044 (13)	0.0054 (14)	0.0058 (16)
C14	0.0548 (16)	0.0751 (18)	0.085 (2)	0.0171 (14)	0.0291 (16)	0.0245 (17)
C15	0.087 (2)	0.0697 (19)	0.079 (2)	0.0193 (17)	0.0405 (19)	0.0017 (16)
C16	0.0689 (17)	0.0584 (15)	0.0520 (15)	−0.0008 (13)	0.0132 (13)	−0.0049 (12)

S1—O2	1.428 (2)	C6—H6	0.9300
S1—O1	1.4371 (18)	C7—H7	0.9300
S1—N1	1.633 (2)	C8—H8	0.9300
S1—C5	1.755 (3)	C9—C10	1.510 (5)
N1—C8	1.301 (3)	C9—H9A	0.9700
N2—C8	1.326 (3)	C9—H9B	0.9700
N2—C11	1.441 (3)	C10—H10A	0.9600
N2—C9	1.467 (3)	C10—H10B	0.9600
C1—C2	1.517 (4)	C10—H10C	0.9600
C1—H1A	0.9600	C11—C12	1.369 (3)
C1—H1B	0.9600	C11—C16	1.379 (4)
C1—H1C	0.9600	C12—C13	1.377 (4)
C2—C7	1.363 (4)	C12—H12	0.9300
C2—C3	1.373 (4)	C13—C14	1.361 (4)
C3—C4	1.376 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.353 (4)
C4—C5	1.374 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.381 (4)
C5—C6	1.371 (4)	C15—H15	0.9300
C6—C7	1.376 (4)	C16—H16	0.9300
O2—S1—O1	117.23 (12)	N1—C8—N2	122.7 (2)
O2—S1—N1	107.27 (12)	N1—C8—H8	118.6
O1—S1—N1	112.35 (10)	N2—C8—H8	118.6
O2—S1—C5	107.76 (11)	N2—C9—C10	111.4 (2)
O1—S1—C5	107.95 (12)	N2—C9—H9A	109.3
N1—S1—C5	103.32 (11)	C10—C9—H9A	109.3
C8—N1—S1	116.09 (17)	N2—C9—H9B	109.3
C8—N2—C11	119.30 (19)	C10—C9—H9B	109.3
C8—N2—C9	121.8 (2)	H9A—C9—H9B	108.0
C11—N2—C9	118.42 (19)	C9—C10—H10A	109.5
C2—C1—H1A	109.5	C9—C10—H10B	109.5
C2—C1—H1B	109.5	H10A—C10—H10B	109.5
H1A—C1—H1B	109.5	C9—C10—H10C	109.5
C2—C1—H1C	109.5	H10A—C10—H10C	109.5
H1A—C1—H1C	109.5	H10B—C10—H10C	109.5
H1B—C1—H1C	109.5	C12—C11—C16	120.1 (2)
C7—C2—C3	118.3 (3)	C12—C11—N2	119.6 (2)
C7—C2—C1	121.3 (3)	C16—C11—N2	120.3 (2)
C3—C2—C1	120.4 (3)	C11—C12—C13	119.2 (3)
C2—C3—C4	121.2 (3)	C11—C12—H12	120.4
C2—C3—H3	119.4	C13—C12—H12	120.4
C4—C3—H3	119.4	C14—C13—C12	120.9 (3)
C5—C4—C3	119.7 (3)	C14—C13—H13	119.5
C5—C4—H4	120.2	C12—C13—H13	119.5
C3—C4—H4	120.2	C15—C14—C13	119.9 (3)
C6—C5—C4	119.6 (3)	C15—C14—H14	120.0
C6—C5—S1	120.3 (2)	C13—C14—H14	120.0
C4—C5—S1	120.1 (2)	C14—C15—C16	120.5 (3)
C5—C6—C7	119.7 (3)	C14—C15—H15	119.8
C5—C6—H6	120.2	C16—C15—H15	119.8
C7—C6—H6	120.2	C11—C16—C15	119.4 (3)
C2—C7—C6	121.6 (3)	C11—C16—H16	120.3
C2—C7—H7	119.2	C15—C16—H16	120.3
C6—C7—H7	119.2
O2—S1—N1—C8	−125.18 (19)	C5—C6—C7—C2	−1.5 (5)
O1—S1—N1—C8	5.1 (2)	S1—N1—C8—N2	−178.33 (18)
C5—S1—N1—C8	121.1 (2)	C11—N2—C8—N1	−173.9 (2)
C7—C2—C3—C4	−0.9 (5)	C9—N2—C8—N1	−1.9 (4)
C1—C2—C3—C4	−179.5 (3)	C8—N2—C9—C10	−96.1 (3)
C2—C3—C4—C5	0.6 (5)	C11—N2—C9—C10	76.0 (3)
C3—C4—C5—C6	−0.7 (4)	C8—N2—C11—C12	55.5 (3)
C3—C4—C5—S1	177.3 (2)	C9—N2—C11—C12	−116.7 (3)
O2—S1—C5—C6	154.6 (2)	C8—N2—C11—C16	−124.7 (3)
O1—S1—C5—C6	27.1 (3)	C9—N2—C11—C16	63.1 (3)
N1—S1—C5—C6	−92.1 (2)	C16—C11—C12—C13	0.3 (4)
O2—S1—C5—C4	−23.4 (2)	N2—C11—C12—C13	−179.9 (2)
O1—S1—C5—C4	−150.9 (2)	C11—C12—C13—C14	0.2 (4)
N1—S1—C5—C4	89.9 (2)	C12—C13—C14—C15	0.2 (5)
C4—C5—C6—C7	1.1 (5)	C13—C14—C15—C16	−1.0 (5)
S1—C5—C6—C7	−176.9 (3)	C12—C11—C16—C15	−1.2 (4)
C3—C2—C7—C6	1.3 (5)	N2—C11—C16—C15	179.1 (2)
C1—C2—C7—C6	179.9 (3)	C14—C15—C16—C11	1.5 (4)