(E)-4-Amino-N-(1,2-dihydro-pyridin-2-yl-idene)benzene-sulfonamide nitro-methane monosolvate.

In the title solvate, C(11)H(11)N(3)O(2)S·CH(3)NO(2), the dihedral angle between the benzene ring and the N-containing ring is 85.94 (11)°, and an approximate V shape arises for the sulfonamide mol-ecule. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds and weak C-H⋯O inter-actions link the sulfonamide mol-ecules into a three-dimensional network. The nitro-methane solvent mol-ecules are located in the inter-stitial sites in the sulfonamide network.

Related literature

For background to the applications of sulfonamide compounds, see: Ghorab et al. (2009 ▶);

Experimental

Crystal data

C11H11N3O2S·CH3NO2

M = 310.34

Orthorhombic,

a = 10.5179 (3) Å

b = 12.4857 (3) Å

c = 22.7237 (6) Å

V = 2984.15 (14) Å3

Z = 8

Cu Kα radiation

μ = 2.14 mm−1

T = 296 K

0.54 × 0.43 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.392, T max = 0.554

14569 measured reflections

2799 independent reflections

2386 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.144

S = 1.07

2799 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.42 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009865/hb6660sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009865/hb6660Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009865/hb6660Isup3.cml

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

C11H11N3O2S·CH3NO2	F(000) = 1296
Mr = 310.34	Dx = 1.381 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2799 reflections
a = 10.5179 (3) Å	θ = 5.7–71.6°
b = 12.4857 (3) Å	µ = 2.14 mm−1
c = 22.7237 (6) Å	T = 296 K
V = 2984.15 (14) Å3	Block, pink
Z = 8	0.54 × 0.43 × 0.31 mm

Bruker SMART APEXII CCD diffractometer	2799 independent reflections
Radiation source: fine-focus sealed tube	2386 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 71.6°, θmin = 5.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
Tmin = 0.392, Tmax = 0.554	k = −15→15
14569 measured reflections	l = −27→27

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0843P)2 + 0.5181P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2799 reflections	Δρmax = 0.25 e Å−3
196 parameters	Δρmin = −0.42 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.03202 (5)	0.52678 (4)	0.13912 (2)	0.0537 (2)
O1	−0.04470 (16)	0.62229 (11)	0.13586 (7)	0.0664 (4)
O2	0.14832 (16)	0.53613 (12)	0.17203 (7)	0.0696 (4)
N1	0.05275 (16)	0.49231 (13)	0.07212 (8)	0.0549 (4)
N2	−0.27661 (19)	0.18108 (17)	0.24298 (10)	0.0806 (6)
H1N2	−0.2408	0.1417	0.2699	0.097*
H2N2	−0.3364	0.1534	0.2213	0.097*
N3	0.13565 (17)	0.39072 (14)	−0.00078 (8)	0.0587 (4)
H1N3	0.082 (2)	0.4266 (17)	−0.0216 (10)	0.054 (6)*
C1	−0.05963 (18)	0.42658 (14)	0.17206 (8)	0.0499 (4)
C2	−0.1786 (2)	0.40208 (16)	0.14851 (9)	0.0547 (5)
H2A	−0.2093	0.4405	0.1165	0.066*
C3	−0.2504 (2)	0.32171 (17)	0.17237 (9)	0.0576 (5)
H3A	−0.3299	0.3063	0.1565	0.069*
C4	−0.20549 (19)	0.26212 (16)	0.22053 (9)	0.0567 (5)
C5	−0.0891 (2)	0.29027 (18)	0.24482 (9)	0.0628 (5)
H5A	−0.0599	0.2542	0.2780	0.075*
C6	−0.0163 (2)	0.37042 (17)	0.22084 (9)	0.0576 (5)
H6A	0.0623	0.3871	0.2373	0.069*
C7	0.13465 (18)	0.41433 (15)	0.05728 (9)	0.0530 (4)
C8	0.2136 (2)	0.3168 (2)	−0.02582 (12)	0.0741 (6)
H8A	0.2104	0.3049	−0.0662	0.089*
C9	0.2955 (3)	0.2609 (2)	0.00786 (14)	0.0855 (8)
H9A	0.3498	0.2106	−0.0088	0.103*
C10	0.2968 (3)	0.2799 (2)	0.06752 (14)	0.0857 (8)
H10A	0.3523	0.2413	0.0913	0.103*
C11	0.2185 (2)	0.35419 (18)	0.09265 (11)	0.0708 (6)
H11A	0.2205	0.3651	0.1331	0.085*
O3	0.0798 (3)	0.0856 (2)	0.04675 (11)	0.1239 (9)
O4	−0.0699 (2)	−0.0317 (2)	0.06434 (11)	0.1120 (8)
N4	0.0045 (3)	0.0378 (3)	0.08153 (15)	0.1093 (9)
C12	0.0102 (4)	0.0684 (4)	0.14512 (17)	0.1265 (14)
H12A	−0.0722	0.0921	0.1578	0.190*
H12B	0.0706	0.1253	0.1503	0.190*
H12C	0.0358	0.0076	0.1681	0.190*

	U11	U22	U33	U12	U13	U23
S1	0.0566 (4)	0.0492 (3)	0.0551 (3)	−0.00291 (18)	−0.00473 (19)	−0.00030 (17)
O1	0.0793 (11)	0.0487 (8)	0.0712 (10)	0.0061 (7)	0.0029 (7)	0.0001 (6)
O2	0.0653 (10)	0.0710 (9)	0.0724 (10)	−0.0133 (7)	−0.0152 (8)	−0.0063 (7)
N1	0.0541 (9)	0.0559 (8)	0.0546 (9)	0.0045 (7)	−0.0008 (7)	0.0066 (7)
N2	0.0624 (12)	0.0869 (13)	0.0923 (15)	−0.0077 (10)	−0.0068 (10)	0.0371 (11)
N3	0.0544 (10)	0.0631 (9)	0.0587 (10)	0.0083 (8)	−0.0006 (8)	0.0047 (8)
C1	0.0513 (10)	0.0518 (9)	0.0464 (9)	0.0002 (8)	−0.0059 (7)	−0.0004 (7)
C2	0.0549 (11)	0.0588 (10)	0.0505 (10)	0.0017 (8)	−0.0082 (8)	0.0071 (8)
C3	0.0479 (10)	0.0659 (11)	0.0589 (11)	−0.0003 (8)	−0.0077 (8)	0.0038 (9)
C4	0.0494 (10)	0.0626 (10)	0.0580 (11)	0.0039 (9)	0.0040 (8)	0.0082 (8)
C5	0.0618 (13)	0.0740 (12)	0.0525 (10)	0.0043 (10)	−0.0075 (9)	0.0153 (9)
C6	0.0546 (11)	0.0663 (11)	0.0518 (11)	−0.0017 (9)	−0.0110 (8)	0.0050 (8)
C7	0.0476 (10)	0.0520 (9)	0.0595 (11)	−0.0021 (8)	−0.0016 (8)	0.0072 (8)
C8	0.0688 (14)	0.0791 (14)	0.0744 (14)	0.0156 (12)	0.0052 (11)	−0.0043 (11)
C9	0.0784 (17)	0.0795 (15)	0.0985 (19)	0.0293 (14)	0.0006 (14)	−0.0035 (14)
C10	0.0832 (17)	0.0737 (14)	0.100 (2)	0.0258 (13)	−0.0213 (15)	0.0060 (13)
C11	0.0739 (15)	0.0672 (12)	0.0712 (14)	0.0110 (11)	−0.0150 (11)	0.0046 (10)
O3	0.1205 (18)	0.148 (2)	0.1029 (17)	−0.0638 (17)	0.0212 (14)	−0.0115 (15)
O4	0.0996 (15)	0.141 (2)	0.0955 (15)	−0.0502 (15)	0.0236 (13)	−0.0211 (13)
N4	0.0867 (17)	0.139 (2)	0.103 (2)	−0.0042 (17)	0.0109 (16)	−0.0112 (17)
C12	0.122 (3)	0.169 (4)	0.089 (2)	−0.013 (3)	0.004 (2)	−0.033 (2)

S1—O2	1.4384 (16)	C5—C6	1.373 (3)
S1—O1	1.4418 (15)	C5—H5A	0.9300
S1—N1	1.5971 (18)	C6—H6A	0.9300
S1—C1	1.7477 (19)	C7—C11	1.410 (3)
N1—C7	1.343 (3)	C8—C9	1.347 (4)
N2—C4	1.358 (3)	C8—H8A	0.9300
N2—H1N2	0.8700	C9—C10	1.377 (4)
N2—H2N2	0.8699	C9—H9A	0.9300
N3—C7	1.352 (3)	C10—C11	1.365 (4)
N3—C8	1.359 (3)	C10—H10A	0.9300
N3—H1N3	0.86 (2)	C11—H11A	0.9300
C1—C6	1.389 (3)	O3—N4	1.268 (4)
C1—C2	1.395 (3)	O4—N4	1.232 (4)
C2—C3	1.368 (3)	N4—C12	1.496 (5)
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.405 (3)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C4—C5	1.388 (3)
O2—S1—O1	115.82 (10)	C5—C6—C1	120.10 (19)
O2—S1—N1	113.66 (10)	C5—C6—H6A	119.9
O1—S1—N1	104.49 (9)	C1—C6—H6A	119.9
O2—S1—C1	107.73 (10)	N1—C7—N3	114.09 (17)
O1—S1—C1	107.78 (9)	N1—C7—C11	130.1 (2)
N1—S1—C1	106.90 (9)	N3—C7—C11	115.81 (19)
C7—N1—S1	121.49 (14)	C9—C8—N3	120.0 (2)
C4—N2—H1N2	116.5	C9—C8—H8A	120.0
C4—N2—H2N2	118.8	N3—C8—H8A	120.0
H1N2—N2—H2N2	119.1	C8—C9—C10	118.4 (2)
C7—N3—C8	124.15 (19)	C8—C9—H9A	120.8
C7—N3—H1N3	114.7 (15)	C10—C9—H9A	120.8
C8—N3—H1N3	121.1 (16)	C11—C10—C9	121.5 (2)
C6—C1—C2	119.35 (18)	C11—C10—H10A	119.2
C6—C1—S1	121.47 (15)	C9—C10—H10A	119.2
C2—C1—S1	119.17 (15)	C10—C11—C7	120.0 (2)
C3—C2—C1	120.26 (18)	C10—C11—H11A	120.0
C3—C2—H2A	119.9	C7—C11—H11A	120.0
C1—C2—H2A	119.9	O4—N4—O3	122.0 (3)
C2—C3—C4	120.77 (19)	O4—N4—C12	120.8 (3)
C2—C3—H3A	119.6	O3—N4—C12	117.2 (3)
C4—C3—H3A	119.6	N4—C12—H12A	109.5
N2—C4—C5	121.67 (19)	N4—C12—H12B	109.5
N2—C4—C3	120.14 (19)	H12A—C12—H12B	109.5
C5—C4—C3	118.18 (19)	N4—C12—H12C	109.5
C6—C5—C4	121.24 (18)	H12A—C12—H12C	109.5
C6—C5—H5A	119.4	H12B—C12—H12C	109.5
C4—C5—H5A	119.4
O2—S1—N1—C7	43.60 (19)	C3—C4—C5—C6	−3.3 (3)
O1—S1—N1—C7	170.79 (16)	C4—C5—C6—C1	1.3 (3)
C1—S1—N1—C7	−75.12 (17)	C2—C1—C6—C5	1.2 (3)
O2—S1—C1—C6	−0.9 (2)	S1—C1—C6—C5	−178.33 (17)
O1—S1—C1—C6	−126.50 (18)	S1—N1—C7—N3	176.39 (14)
N1—S1—C1—C6	121.65 (17)	S1—N1—C7—C11	−3.6 (3)
O2—S1—C1—C2	179.59 (16)	C8—N3—C7—N1	178.0 (2)
O1—S1—C1—C2	53.96 (18)	C8—N3—C7—C11	−2.0 (3)
N1—S1—C1—C2	−57.89 (18)	C7—N3—C8—C9	0.8 (4)
C6—C1—C2—C3	−1.6 (3)	N3—C8—C9—C10	0.6 (4)
S1—C1—C2—C3	177.94 (16)	C8—C9—C10—C11	−0.6 (5)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C11—C7	−0.7 (4)
C2—C3—C4—N2	−178.6 (2)	N1—C7—C11—C10	−178.1 (2)
C2—C3—C4—C5	2.9 (3)	N3—C7—C11—C10	1.9 (3)
N2—C4—C5—C6	178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.87	2.10	2.971 (3)	174
N2—H2N2···O1ii	0.87	2.34	3.162 (3)	157
N3—H1N3···N1iii	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A···O1iii	0.93	2.52	3.160 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.87	2.10	2.971 (3)	174
N2—H2N2⋯O1ii	0.87	2.34	3.162 (3)	157
N3—H1N3⋯N1iii	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A⋯O1iii	0.93	2.52	3.160 (3)	126

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