1-Azido-N′-(phenylsulfonyl)methan­imid­amide

Abstract

In the title compound, C₇H₇N₅O₂S, the aromatic ring is oriented at dihedral angles of 79.46 (2) and 89.17 (2)°, respectively, with respect to the amino­(azido)­methyl and the S(6) six-membered ring motif generated by an intra­molecular N—H⋯O inter­action [N⋯O = 2.8901 (15) Å]. Inter­molecular N—H⋯O hydrogen bonds [N⋯O = 2.9177 (15) and 2.9757 (15) Å] generate an infinite one-dimensional network along the base vector (010).

Related literature

For the synthesis, see: Mahmood et al. (2011 ▶). For related structures, see: Denny et al. (1980 ▶); Mahmood et al. (2011 ▶); Müller & Bärnighausen (1970 ▶). For graph-set notations, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

• C₇H₇N₅O₂S

• M _r = 225.24

• Triclinic,

• a = 7.0399 (2) Å

• b = 7.1714 (2) Å

• c = 10.3670 (3) Å

• α = 90.267 (1)°

• β = 98.997 (1)°

• γ = 110.358 (1)°

• V = 483.67 (2) ų

• Z = 2

• Mo Kα radiation

• μ = 0.32 mm⁻¹

• T = 296 K

• 0.35 × 0.31 × 0.12 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.896, T _max = 0.962

• 8598 measured reflections

• 2422 independent reflections

• 2246 reflections with I > 2σ(I)

• R _int = 0.025

Refinement

• R[F ² > 2σ(F ²)] = 0.032

• wR(F ²) = 0.097

• S = 1.06

• 2422 reflections

• 143 parameters

• 3 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.30 e Å⁻³

• Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811037718/pv2447Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O1i	0.85 (1)	2.10 (1)	2.9177 (15)	163 (2)
N2—H2N⋯O2ii	0.84 (1)	2.23 (1)	2.9757 (15)	148 (2)
N2—H2N⋯O2	0.84 (1)	2.33 (2)	2.8901 (15)	125 (2)

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

In continuation to our studies on sulfonamide derivatives we now report the structure of the title compound which is an analogue of the compound reported earlier (Mahmood et al., 2011),

In the title molecule (Fig. 1), the azido group (N3/N4/N5) carries cationic and anionic characters as observed in the previously report compound and reportedin the literature (Denny et al., 1980; Müller & Bärnighausen, 1970). The bond distance N4—N5 is 1.105 (19) Å, which clearly indicates its tripple bond character (N≡N = 1.10 Å) The other bond distances, C7—N1 = 1.3105 (15) Å & C7—N3 = 1.4022 (16) Å represent C to N double and single covalent bonds, respectively. The planer amino(azido)methyl (N1/C8/N2/N3/N4/N5) moiety (r. m. s. deviation of 0.0164 A°) is oriented at a dihedral angle of 79.46 (6)° with respect to the toluene ring. The intramolecular hydrogen bond N2—H2N···O2 produces a six membered ring motif S(6) (Bernstein et al., 1995) which is inclined almost perpendicular (89.17 (2)°) to the aromatic ring (C1—C6). The intermolecular hydrogen bonds are very much in accord with the corresponding hydrogen bonding reported in the previous analogue (Mahmood et al., 2011) as it forms dimers which are further connected through N—H···O type interactions and extended along the b axis (Table. 2, Figure. 2).

Experimental

The titile compound was prepared in accordance with reported method (Mahmood et al., 2011) and recrystalized from a mixture of methanol and ethylacetate (1:1) by slow evaporation.

Refinement

All C—H H atoms were positioned geometrically with C_aromatic—H = 0.93 and treated as with U_iso(H) = 1.2 U_eq(C). The hydrogen atoms bonded to N2 were located via from a fourier map and were included in the refinement with N—H distancs constrained at 0.84 (1) Å with U_iso(H) = 1.5 U_eq(N). The reflection 0 0 1 has been omitted in final refinement.

Figures

Fig. 1.

Thermal ellipsoid plot of the title compound drawn at 50% probability level showing the intramolecular hydrogen bonding via dshed line.

Fig. 2.

Unit cell packing diagram showing the hydrogen bonds via dshed lines, the hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data

C7H7N5O2S	Z = 2
Mr = 225.24	F(000) = 232
Triclinic, P1	Dx = 1.547 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0399 (2) Å	Cell parameters from 6153 reflections
b = 7.1714 (2) Å	θ = 3.0–28.5°
c = 10.3670 (3) Å	µ = 0.32 mm−1
α = 90.267 (1)°	T = 296 K
β = 98.997 (1)°	Plate, colourless
γ = 110.358 (1)°	0.35 × 0.31 × 0.12 mm
V = 483.67 (2) Å3

Data collection

Bruker APEXII CCD diffractometer	2422 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.896, Tmax = 0.962	k = −9→9
8598 measured reflections	l = −13→13

Refinement

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.059P)2 + 0.1064P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2422 reflections	Δρmax = 0.30 e Å−3
143 parameters	Δρmin = −0.30 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.178 (13)

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.29872 (4)	0.66106 (4)	0.14334 (3)	0.03096 (13)
O1	0.22775 (17)	0.82450 (15)	0.15249 (12)	0.0501 (3)
O2	0.37880 (15)	0.63793 (15)	0.02689 (9)	0.0407 (2)
N4	−0.18866 (18)	0.17258 (17)	0.21333 (12)	0.0412 (3)
N3	−0.05785 (18)	0.12367 (17)	0.16650 (12)	0.0406 (3)
C7	0.10971 (19)	0.28677 (17)	0.14142 (11)	0.0297 (2)
N1	0.11035 (16)	0.46635 (15)	0.16629 (10)	0.0318 (2)
N2	0.24609 (19)	0.22835 (17)	0.09706 (13)	0.0405 (3)
H2N	0.346 (2)	0.310 (2)	0.0691 (19)	0.061*
H1N	0.230 (3)	0.1058 (15)	0.096 (2)	0.061*
N5	−0.3157 (2)	0.1915 (2)	0.25610 (18)	0.0632 (4)
C1	0.49613 (19)	0.69027 (18)	0.27813 (12)	0.0317 (3)
C2	0.6735 (2)	0.6594 (2)	0.26000 (14)	0.0415 (3)
H2	0.6882	0.6209	0.1775	0.050*
C3	0.8287 (3)	0.6865 (3)	0.36578 (18)	0.0598 (5)
H3	0.9484	0.6653	0.3549	0.072*
C4	0.8055 (3)	0.7449 (3)	0.48716 (18)	0.0676 (5)
H4	0.9109	0.7641	0.5579	0.081*
C6	0.4725 (3)	0.7480 (3)	0.40091 (15)	0.0498 (4)
H6	0.3525	0.7680	0.4125	0.060*
C5	0.6289 (3)	0.7752 (3)	0.50550 (17)	0.0650 (5)
H5	0.6150	0.8141	0.5882	0.078*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.03183 (19)	0.02277 (18)	0.04005 (19)	0.01043 (12)	0.00916 (12)	0.00792 (11)
O1	0.0508 (6)	0.0279 (5)	0.0787 (8)	0.0209 (5)	0.0146 (5)	0.0126 (5)
O2	0.0400 (5)	0.0447 (6)	0.0364 (5)	0.0115 (4)	0.0113 (4)	0.0105 (4)
N4	0.0348 (6)	0.0323 (6)	0.0514 (7)	0.0040 (5)	0.0105 (5)	0.0104 (5)
N3	0.0391 (6)	0.0269 (5)	0.0526 (7)	0.0052 (5)	0.0138 (5)	0.0038 (5)
C7	0.0306 (6)	0.0250 (5)	0.0314 (5)	0.0078 (4)	0.0040 (4)	0.0044 (4)
N1	0.0294 (5)	0.0253 (5)	0.0416 (5)	0.0092 (4)	0.0095 (4)	0.0040 (4)
N2	0.0444 (7)	0.0260 (5)	0.0560 (7)	0.0136 (5)	0.0194 (5)	0.0053 (5)
N5	0.0470 (8)	0.0558 (9)	0.0908 (11)	0.0143 (7)	0.0320 (8)	0.0185 (8)
C1	0.0327 (6)	0.0232 (5)	0.0370 (6)	0.0058 (4)	0.0086 (5)	0.0025 (4)
C2	0.0364 (7)	0.0482 (8)	0.0397 (6)	0.0144 (6)	0.0074 (5)	−0.0006 (6)
C3	0.0377 (8)	0.0830 (13)	0.0552 (9)	0.0204 (8)	0.0000 (7)	0.0004 (9)
C4	0.0518 (10)	0.0894 (15)	0.0448 (8)	0.0108 (10)	−0.0068 (7)	−0.0014 (8)
C6	0.0487 (8)	0.0557 (9)	0.0453 (8)	0.0155 (7)	0.0158 (6)	−0.0042 (7)
C5	0.0696 (12)	0.0791 (13)	0.0376 (7)	0.0152 (10)	0.0099 (8)	−0.0089 (8)

Geometric parameters (Å, °)

S1—O1	1.4330 (10)	C1—C2	1.3811 (19)
S1—O2	1.4419 (10)	C1—C6	1.3885 (18)
S1—N1	1.6057 (11)	C2—C3	1.382 (2)
S1—C1	1.7650 (13)	C2—H2	0.9300
N4—N5	1.1055 (19)	C3—C4	1.376 (3)
N4—N3	1.2529 (17)	C3—H3	0.9300
N3—C7	1.4022 (16)	C4—C5	1.375 (3)
C7—N1	1.3105 (15)	C4—H4	0.9300
C7—N2	1.3134 (16)	C6—C5	1.379 (3)
N2—H2N	0.837 (9)	C6—H6	0.9300
N2—H1N	0.846 (9)	C5—H5	0.9300
O1—S1—O2	117.23 (7)	C6—C1—S1	119.38 (11)
O1—S1—N1	105.53 (6)	C1—C2—C3	119.31 (14)
O2—S1—N1	112.47 (6)	C1—C2—H2	120.3
O1—S1—C1	107.62 (7)	C3—C2—H2	120.3
O2—S1—C1	107.32 (6)	C4—C3—C2	119.78 (16)
N1—S1—C1	106.07 (6)	C4—C3—H3	120.1
N5—N4—N3	171.37 (15)	C2—C3—H3	120.1
N4—N3—C7	113.51 (11)	C5—C4—C3	121.01 (17)
N1—C7—N2	130.53 (12)	C5—C4—H4	119.5
N1—C7—N3	118.15 (11)	C3—C4—H4	119.5
N2—C7—N3	111.31 (11)	C5—C6—C1	119.30 (15)
C7—N1—S1	121.29 (9)	C5—C6—H6	120.4
C7—N2—H2N	120.8 (13)	C1—C6—H6	120.4
C7—N2—H1N	118.7 (13)	C4—C5—C6	119.79 (16)
H2N—N2—H1N	120.5 (18)	C4—C5—H5	120.1
C2—C1—C6	120.81 (13)	C6—C5—H5	120.1
C2—C1—S1	119.80 (10)
N4—N3—C7—N1	−1.19 (18)	O2—S1—C1—C6	169.50 (11)
N4—N3—C7—N2	177.67 (12)	N1—S1—C1—C6	−70.08 (12)
N2—C7—N1—S1	0.0 (2)	C6—C1—C2—C3	0.0 (2)
N3—C7—N1—S1	178.63 (9)	S1—C1—C2—C3	178.76 (13)
O1—S1—N1—C7	167.67 (11)	C1—C2—C3—C4	−0.5 (3)
O2—S1—N1—C7	38.71 (12)	C2—C3—C4—C5	0.6 (3)
C1—S1—N1—C7	−78.31 (11)	C2—C1—C6—C5	0.2 (2)
O1—S1—C1—C2	−136.24 (12)	S1—C1—C6—C5	−178.49 (14)
O2—S1—C1—C2	−9.24 (13)	C3—C4—C5—C6	−0.3 (4)
N1—S1—C1—C2	111.19 (12)	C1—C6—C5—C4	−0.1 (3)
O1—S1—C1—C6	42.49 (13)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1i	0.85 (1)	2.10 (1)	2.9177 (15)	163.(2)
N2—H2N···O2ii	0.84 (1)	2.23 (1)	2.9757 (15)	148.(2)
N2—H2N···O2	0.84 (1)	2.33 (2)	2.8901 (15)	125.(2)

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