4-(4-Nitro-benzene-sulfonamido)pyridinium trichloro-acetate.

In the crystal structure of the title compound, C(11)H(10)N(3)O(4)S·C(2)Cl(3)O(2), the dihedral angle between the two six-membered rings is 69.2 (1)°. The mol-ecules are connected via inter-molecular N-H⋯O hydrogen bonding.

Related literature

For related literature, see: Talley et al. (2000 ▶); El-Naggar et al. (1981 ▶).

Experimental

Crystal data

C11H10N3O4S·C2Cl3O2

M = 442.65

Monoclinic,

a = 22.017 (4) Å

b = 6.2187 (12) Å

c = 12.719 (3) Å

β = 97.48 (3)°

V = 1726.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 113 (2) K

0.14 × 0.12 × 0.04 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.910, T max = 0.973

9585 measured reflections

3017 independent reflections

2440 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.162

S = 1.16

3017 reflections

243 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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 datablocks I, global. DOI: 10.1107/S160053680800069X/nc2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800069X/nc2087Isup2.hkl

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

C11H10N3O4S1·C2Cl3O2	F000 = 896
Mr = 442.65	Dx = 1.703 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 22.017 (4) Å	Cell parameters from 4622 reflections
b = 6.2187 (12) Å	θ = 1.8–28.1º
c = 12.719 (3) Å	µ = 0.69 mm−1
β = 97.48 (3)º	T = 113 (2) K
V = 1726.6 (6) Å3	Lamellar, colorless
Z = 4	0.14 × 0.12 × 0.04 mm

Rigaku Saturn diffractometer	3017 independent reflections
Radiation source: rotating anode	2440 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.059
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 111(2) K	θmin = 1.9º
ω scans	h = −26→26
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −7→7
Tmin = 0.910, Tmax = 0.973	l = −15→13
9585 measured reflections

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0873P)2] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
3017 reflections	Δρmax = 0.57 e Å−3
243 parameters	Δρmin = −0.53 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.18257 (4)	1.36555 (14)	0.07245 (7)	0.0191 (3)
O1	0.18542 (11)	1.5313 (4)	0.1516 (2)	0.0249 (6)
O2	0.16464 (11)	1.4166 (4)	−0.03720 (19)	0.0246 (6)
O3	0.04962 (13)	0.5416 (5)	0.2777 (2)	0.0357 (7)
O4	−0.00146 (13)	0.5394 (5)	0.1197 (2)	0.0409 (8)
N1	0.30157 (14)	0.6878 (5)	−0.0407 (3)	0.0231 (7)
N2	0.25080 (13)	1.2586 (5)	0.0880 (2)	0.0193 (7)
N3	0.03717 (14)	0.6156 (5)	0.1877 (3)	0.0248 (7)
C1	0.26602 (16)	1.0661 (5)	0.0425 (3)	0.0182 (8)
C2	0.31203 (16)	0.9400 (6)	0.0978 (3)	0.0219 (8)
H2A	0.3310	0.9837	0.1639	0.026*
C3	0.32893 (16)	0.7525 (6)	0.0544 (3)	0.0241 (8)
H3	0.3597	0.6688	0.0910	0.029*
C4	0.25743 (16)	0.8040 (6)	−0.0958 (3)	0.0225 (8)
H4	0.2395	0.7554	−0.1618	0.027*
C5	0.23811 (16)	0.9937 (6)	−0.0568 (3)	0.0209 (8)
H5	0.2071	1.0732	−0.0954	0.025*
C6	0.13549 (15)	1.1534 (5)	0.1065 (3)	0.0185 (8)
C7	0.09757 (15)	1.0470 (6)	0.0274 (3)	0.0213 (8)
H7	0.0944	1.0934	−0.0426	0.026*
C8	0.06426 (16)	0.8695 (6)	0.0547 (3)	0.0216 (8)
H8	0.0387	0.7945	0.0034	0.026*
C9	0.07022 (15)	0.8085 (6)	0.1592 (3)	0.0209 (8)
C10	0.10690 (16)	0.9146 (6)	0.2399 (3)	0.0219 (8)
H10	0.1088	0.8706	0.3101	0.026*
C11	0.14059 (16)	1.0888 (6)	0.2117 (3)	0.0232 (8)
H11	0.1665	1.1622	0.2632	0.028*
Cl1	0.43685 (4)	0.58693 (15)	0.39003 (8)	0.0283 (3)
Cl2	0.46462 (5)	0.17077 (17)	0.30622 (9)	0.0365 (3)
Cl3	0.41727 (4)	0.20184 (16)	0.50681 (7)	0.0291 (3)
O5	0.31493 (11)	0.1505 (4)	0.33912 (19)	0.0230 (6)
O6	0.33887 (11)	0.4175 (4)	0.2360 (2)	0.0265 (6)
C12	0.41404 (16)	0.3150 (6)	0.3785 (3)	0.0212 (8)
C13	0.34910 (16)	0.2939 (5)	0.3118 (3)	0.0180 (7)
H1	0.3107 (17)	0.568 (4)	−0.075 (3)	0.028 (11)*
H2	0.2756 (17)	1.324 (6)	0.140 (3)	0.047 (13)*

	U11	U22	U33	U12	U13	U23
S1	0.0240 (5)	0.0171 (5)	0.0161 (5)	0.0033 (3)	0.0022 (3)	0.0002 (3)
O1	0.0307 (14)	0.0182 (13)	0.0257 (15)	0.0037 (10)	0.0031 (11)	−0.0061 (11)
O2	0.0322 (15)	0.0251 (14)	0.0160 (14)	0.0029 (11)	0.0009 (10)	0.0055 (11)
O3	0.0403 (16)	0.0382 (17)	0.0280 (17)	−0.0053 (13)	0.0023 (12)	0.0112 (14)
O4	0.0468 (18)	0.0483 (19)	0.0276 (17)	−0.0252 (14)	0.0044 (13)	−0.0050 (14)
N1	0.0314 (18)	0.0155 (16)	0.0247 (19)	−0.0008 (13)	0.0120 (13)	−0.0028 (13)
N2	0.0231 (15)	0.0191 (16)	0.0148 (17)	0.0006 (12)	−0.0004 (11)	−0.0027 (13)
N3	0.0277 (18)	0.0256 (17)	0.0220 (19)	0.0001 (13)	0.0067 (13)	−0.0017 (14)
C1	0.0256 (19)	0.0141 (18)	0.017 (2)	−0.0029 (13)	0.0096 (13)	−0.0001 (14)
C2	0.030 (2)	0.0205 (19)	0.015 (2)	0.0007 (14)	0.0023 (14)	0.0000 (15)
C3	0.032 (2)	0.022 (2)	0.019 (2)	0.0021 (15)	0.0053 (15)	0.0035 (16)
C4	0.029 (2)	0.0226 (19)	0.016 (2)	−0.0038 (15)	0.0052 (14)	−0.0004 (15)
C5	0.0251 (19)	0.0208 (19)	0.0166 (19)	0.0009 (14)	0.0016 (14)	0.0026 (15)
C6	0.0191 (18)	0.0209 (19)	0.016 (2)	0.0038 (13)	0.0030 (13)	−0.0014 (14)
C7	0.0237 (19)	0.029 (2)	0.0108 (18)	0.0007 (15)	0.0006 (13)	0.0008 (15)
C8	0.0214 (19)	0.026 (2)	0.016 (2)	0.0010 (14)	0.0002 (14)	−0.0045 (15)
C9	0.0204 (18)	0.0223 (19)	0.021 (2)	0.0028 (14)	0.0071 (14)	−0.0008 (15)
C10	0.026 (2)	0.027 (2)	0.0127 (19)	0.0015 (15)	0.0040 (14)	−0.0007 (15)
C11	0.026 (2)	0.027 (2)	0.017 (2)	0.0007 (15)	0.0013 (14)	−0.0041 (15)
Cl1	0.0313 (5)	0.0241 (5)	0.0291 (6)	−0.0098 (4)	0.0022 (4)	0.0005 (4)
Cl2	0.0349 (6)	0.0404 (6)	0.0364 (7)	0.0111 (4)	0.0135 (4)	−0.0022 (5)
Cl3	0.0325 (5)	0.0345 (6)	0.0187 (5)	−0.0087 (4)	−0.0031 (4)	0.0073 (4)
O5	0.0286 (14)	0.0216 (14)	0.0182 (15)	−0.0052 (10)	0.0010 (10)	0.0034 (10)
O6	0.0330 (15)	0.0242 (14)	0.0209 (15)	−0.0064 (11)	−0.0021 (11)	0.0070 (11)
C12	0.0234 (19)	0.0205 (19)	0.020 (2)	−0.0016 (14)	0.0040 (14)	0.0010 (15)
C13	0.0238 (18)	0.0173 (18)	0.0130 (19)	0.0004 (14)	0.0031 (13)	−0.0033 (14)

S1—O2	1.435 (2)	C4—H4	0.9300
S1—O1	1.436 (3)	C5—H5	0.9300
S1—N2	1.631 (3)	C6—C11	1.388 (5)
S1—C6	1.766 (4)	C6—C7	1.388 (5)
O3—N3	1.231 (4)	C7—C8	1.394 (5)
O4—N3	1.227 (4)	C7—H7	0.9300
N1—C4	1.335 (5)	C8—C9	1.372 (5)
N1—C3	1.341 (5)	C8—H8	0.9300
N1—H1	0.897 (10)	C9—C10	1.387 (5)
N2—C1	1.390 (4)	C10—C11	1.386 (5)
N2—H2	0.897 (10)	C10—H10	0.9300
N3—C9	1.472 (5)	C11—H11	0.9300
C1—C2	1.397 (5)	Cl1—C12	1.765 (4)
C1—C5	1.405 (5)	Cl2—C12	1.777 (4)
C2—C3	1.362 (5)	Cl3—C12	1.770 (4)
C2—H2A	0.9300	O5—C13	1.245 (4)
C3—H3	0.9300	O6—C13	1.231 (4)
C4—C5	1.368 (5)	C12—C13	1.570 (4)
O2—S1—O1	120.25 (15)	C1—C5—H5	120.6
O2—S1—N2	109.93 (16)	C11—C6—C7	121.7 (3)
O1—S1—N2	104.59 (14)	C11—C6—S1	118.4 (3)
O2—S1—C6	107.91 (16)	C7—C6—S1	119.7 (3)
O1—S1—C6	109.75 (17)	C6—C7—C8	118.9 (3)
N2—S1—C6	103.08 (16)	C6—C7—H7	120.5
C4—N1—C3	121.4 (3)	C8—C7—H7	120.5
C4—N1—H1	113 (2)	C9—C8—C7	118.2 (3)
C3—N1—H1	126 (2)	C9—C8—H8	120.9
C1—N2—S1	124.7 (2)	C7—C8—H8	120.9
C1—N2—H2	123 (3)	C8—C9—C10	123.9 (3)
S1—N2—H2	112 (3)	C8—C9—N3	118.4 (3)
O4—N3—O3	124.1 (3)	C10—C9—N3	117.7 (3)
O4—N3—C9	117.4 (3)	C11—C10—C9	117.4 (3)
O3—N3—C9	118.4 (3)	C11—C10—H10	121.3
N2—C1—C2	118.2 (3)	C9—C10—H10	121.3
N2—C1—C5	123.4 (3)	C10—C11—C6	119.8 (3)
C2—C1—C5	118.4 (3)	C10—C11—H11	120.1
C3—C2—C1	119.7 (3)	C6—C11—H11	120.1
C3—C2—H2A	120.2	C13—C12—Cl1	110.7 (2)
C1—C2—H2A	120.2	C13—C12—Cl3	112.9 (3)
N1—C3—C2	120.5 (3)	Cl1—C12—Cl3	109.12 (19)
N1—C3—H3	119.7	C13—C12—Cl2	105.4 (2)
C2—C3—H3	119.7	Cl1—C12—Cl2	109.6 (2)
N1—C4—C5	121.1 (3)	Cl3—C12—Cl2	108.90 (19)
N1—C4—H4	119.5	O6—C13—O5	127.6 (3)
C5—C4—H4	119.5	O6—C13—C12	115.6 (3)
C4—C5—C1	118.8 (3)	O5—C13—C12	116.8 (3)
C4—C5—H5	120.6
O2—S1—N2—C1	−62.4 (3)	S1—C6—C7—C8	175.1 (3)
O1—S1—N2—C1	167.2 (3)	C6—C7—C8—C9	0.4 (5)
C6—S1—N2—C1	52.4 (3)	C7—C8—C9—C10	0.8 (6)
S1—N2—C1—C2	−148.4 (3)	C7—C8—C9—N3	−177.4 (3)
S1—N2—C1—C5	32.5 (5)	O4—N3—C9—C8	−11.3 (5)
N2—C1—C2—C3	−178.7 (3)	O3—N3—C9—C8	169.0 (3)
C5—C1—C2—C3	0.4 (5)	O4—N3—C9—C10	170.3 (3)
C4—N1—C3—C2	0.3 (6)	O3—N3—C9—C10	−9.4 (5)
C1—C2—C3—N1	−0.3 (6)	C8—C9—C10—C11	−1.8 (6)
C3—N1—C4—C5	−0.4 (6)	N3—C9—C10—C11	176.4 (3)
N1—C4—C5—C1	0.6 (6)	C9—C10—C11—C6	1.6 (5)
N2—C1—C5—C4	178.5 (3)	C7—C6—C11—C10	−0.4 (5)
C2—C1—C5—C4	−0.6 (5)	S1—C6—C11—C10	−176.2 (3)
O2—S1—C6—C11	−174.3 (3)	Cl1—C12—C13—O6	37.9 (4)
O1—S1—C6—C11	−41.5 (3)	Cl3—C12—C13—O6	160.6 (3)
N2—S1—C6—C11	69.5 (3)	Cl2—C12—C13—O6	−80.6 (3)
O2—S1—C6—C7	9.9 (3)	Cl1—C12—C13—O5	−144.5 (3)
O1—S1—C6—C7	142.6 (3)	Cl3—C12—C13—O5	−21.8 (4)
N2—S1—C6—C7	−106.4 (3)	Cl2—C12—C13—O5	97.0 (3)
C11—C6—C7—C8	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.897 (10)	1.755 (13)	2.639 (4)	168 (4)
N2—H2···O6ii	0.897 (10)	1.825 (15)	2.707 (4)	167 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.897 (10)	1.755 (13)	2.639 (4)	168 (4)
N2—H2⋯O6ii	0.897 (10)	1.825 (15)	2.707 (4)	167 (4)

Symmetry codes: (i) ; (ii) .