2-Nitro-N-(4-pyridinio)benzene­sulfonamidate

Li, J.-S.; Yang, D.-W.; Liu, W.-D.

doi:10.1107/S1600536807064410

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o204

https://doi.org/10.1107/S1600536807064410

Open

access

2-Nitro-N-(4-pyridinio)benzenesulfonamidate

Jiang-Sheng Li,^a ^* Dao-Wu Yang ^a and Wei-Dong Liu ^b

^aSchool of Chemical and Environmental Engineering, Changsha University of Science & Technology, Changsha 410076, People's Republic of China, and ^bHunan Research Institute of Chemical Industry, Changsha 410007, People's Republic of China
^*Correspondence e-mail: jansenlee1103@yahoo.com.cn

(Received 20 November 2007; accepted 29 November 2007; online 6 December 2007)

The title compound, C₁₁H₉N₃O₄S, crystallizes with two molecules in the asymmetric unit; each molecule exists as a zwitterion in the solid state. Intermolecular N—H⋯N hydrogen bonds link the molecules into chains. Weak C—H⋯O interactions further stabilize the crystal structure.

Related literature

For zwitterionic forms of N-arylbenzenesulfonamides, see: Yu et al. (2007 ); Amendola et al.(2005 ); Lindley et al. (1977 ); Schaumann et al. (1975 ).

Experimental

Crystal data

C₁₁H₉N₃O₄S
M_r = 279.27
Triclinic, $[P \overline 1]$
a = 7.768 (3) Å
b = 12.570 (5) Å
c = 13.436 (5) Å
α = 75.534 (7)°
β = 85.400 (7)°
γ = 88.741 (6)°
V = 1266.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 294 (2) K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.924, T_max = 0.948
6351 measured reflections
4357 independent reflections
2918 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.174
S = 1.02
4357 reflections
349 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.95 (4)	2.67 (4)	3.215 (4)	117 (3)
N4—H4A⋯N2ⁱ	0.95 (4)	2.08 (4)	2.969 (4)	155 (3)
N1—H1A⋯N5ⁱⁱ	0.88 (5)	2.02 (5)	2.898 (4)	172 (4)
C14—H14⋯O1ⁱ	0.93	2.54	3.140 (5)	122
C14—H14⋯O6ⁱⁱⁱ	0.93	2.58	3.249 (5)	130
C16—H16⋯O1^iv	0.93	2.54	3.265 (5)	135
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y, z; (iii) x-1, y, z; (iv) x, y-1, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064410/bt2635sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064410/bt2635Isup2.hkl

checkCIF report

Comment top

The title compound crystallizes with two molecules in the asymmetric unit; each molecule displays a zwitterion structure with the pyridine N protonated and the amide N deprotonated (Figs. 1 and 2). The relatively short C1—N2 [1.382 (4) Å] and C12—N5 [1.374 (4) Å] distances indicate that the N2 and N5 lone-pair electrons weakly conjugate with pyridinium rings. The benzene ring forms an angle of 85.1 (2) and 89.3 (2)° with the pyridinium ring in the two molecules of the asymmetric unit. In the addition, the nitro group is inclined to the benzene ring with 73.3 (3)°, and 80.0 (4)°. In the crystal, intermolecular N—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into chains.

Related literature top

For zwitterionic forms of N-arylbenzenesulfonamides, see: Yu et al. (2007); Amendola et al.(2005); Lindley et al. (1977); Schaumann et al. (1975).

Experimental top

A solution of 2-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in CH₂Cl₂ (10 ml) was added dropwise to a suspension of 4-aminopyridine (0.9 g, 10 mmol) in CH₂Cl₂ (10 ml) at room temperature with stirring. The reaction mixture was stirring overnight. The yellow solid obtained was washed with warm water in a yield of 70.3%. Yellow blocks were grown from its formic solution.

Structure description top

For zwitterionic forms of N-arylbenzenesulfonamides, see: Yu et al. (2007); Amendola et al.(2005); Lindley et al. (1977); Schaumann et al. (1975).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. Perspective view of one of the two molecules in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. Perspective view of the other molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.

2-Nitro-N-(4-pyridinio)benzenesulfonamidate top

Crystal data top

C₁₁H₉N₃O₄S	Z = 4
M_r = 279.27	F(000) = 576
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.768 (3) Å	Cell parameters from 2204 reflections
b = 12.570 (5) Å	θ = 3.0–24.8°
c = 13.436 (5) Å	µ = 0.27 mm⁻¹
α = 75.534 (7)°	T = 294 K
β = 85.400 (7)°	Block, yellow
γ = 88.741 (6)°	0.30 × 0.24 × 0.20 mm
V = 1266.3 (8) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4357 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.924, T_max = 0.948	k = −14→11
6351 measured reflections	l = −15→11

Refinement top

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) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0887P)² + 0.7778P] where P = (F_o² + 2F_c²)/3
4357 reflections	(Δ/σ)_max = 0.001
349 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₁H₉N₃O₄S	γ = 88.741 (6)°
M_r = 279.27	V = 1266.3 (8) Å³
Triclinic, P1	Z = 4
a = 7.768 (3) Å	Mo Kα radiation
b = 12.570 (5) Å	µ = 0.27 mm⁻¹
c = 13.436 (5) Å	T = 294 K
α = 75.534 (7)°	0.30 × 0.24 × 0.20 mm
β = 85.400 (7)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4357 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2918 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.948	R_int = 0.026
6351 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.40 e Å⁻³
4357 reflections	Δρ_min = −0.26 e Å⁻³
349 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.35624 (11)	1.06378 (7)	0.83977 (8)	0.0438 (3)
S2	0.16866 (12)	0.54595 (7)	0.82807 (9)	0.0484 (3)
O1	0.3338 (3)	1.1734 (2)	0.8574 (2)	0.0530 (7)
O2	0.2218 (3)	0.9840 (2)	0.8878 (2)	0.0605 (8)
O3	0.7821 (5)	1.1047 (4)	0.6529 (3)	0.1145 (16)
O4	0.6473 (5)	1.2478 (4)	0.6875 (3)	0.0885 (12)
O5	0.1958 (4)	0.6616 (2)	0.8216 (3)	0.0646 (9)
O6	0.2869 (3)	0.4682 (2)	0.8871 (2)	0.0619 (8)
O7	−0.1188 (6)	0.6900 (4)	0.6559 (3)	0.1066 (15)
O8	0.1034 (8)	0.7942 (3)	0.6026 (4)	0.141 (2)
N1	0.7802 (4)	0.7241 (3)	0.8638 (3)	0.0519 (9)
H1A	0.828 (6)	0.660 (4)	0.864 (3)	0.062*
N2	0.5495 (4)	1.0267 (2)	0.8668 (2)	0.0408 (7)
N3	0.6518 (5)	1.1607 (4)	0.6602 (3)	0.0714 (11)
N4	−0.2797 (4)	0.2206 (3)	0.9043 (3)	0.0471 (8)
H4A	−0.344 (5)	0.154 (3)	0.914 (3)	0.056*
N5	−0.0324 (4)	0.5224 (2)	0.8627 (3)	0.0439 (8)
N6	0.0329 (7)	0.7048 (4)	0.6261 (4)	0.0840 (13)
C1	0.6149 (4)	0.9243 (3)	0.8638 (3)	0.0367 (8)
C2	0.7930 (5)	0.9064 (3)	0.8816 (3)	0.0467 (10)
H2	0.8574	0.9625	0.8941	0.056*
C3	0.8711 (5)	0.8074 (3)	0.8804 (3)	0.0498 (10)
H3	0.9878	0.7978	0.8910	0.060*
C4	0.6109 (5)	0.7371 (3)	0.8454 (3)	0.0529 (11)
H4	0.5509	0.6790	0.8332	0.063*
C5	0.5256 (5)	0.8354 (3)	0.8445 (3)	0.0469 (9)
H5	0.4097	0.8429	0.8311	0.056*
C6	0.3505 (5)	1.0794 (3)	0.7031 (3)	0.0489 (10)
C7	0.2000 (6)	1.0521 (4)	0.6646 (5)	0.0733 (14)
H7	0.1070	1.0224	0.7104	0.088*
C8	0.1865 (8)	1.0684 (5)	0.5589 (6)	0.0930 (19)
H8	0.0834	1.0522	0.5352	0.112*
C9	0.3248 (9)	1.1085 (5)	0.4890 (5)	0.0883 (19)
H9	0.3158	1.1162	0.4190	0.106*
C10	0.4776 (7)	1.1375 (4)	0.5235 (4)	0.0729 (14)
H10	0.5709	1.1654	0.4773	0.088*
C11	0.4862 (5)	1.1233 (3)	0.6295 (3)	0.0535 (11)
C12	−0.1050 (5)	0.4203 (3)	0.8786 (3)	0.0387 (8)
C13	−0.2877 (4)	0.4112 (3)	0.8968 (3)	0.0435 (9)
H13	−0.3524	0.4731	0.9014	0.052*
C14	−0.3706 (5)	0.3136 (3)	0.9076 (3)	0.0445 (9)
H14	−0.4905	0.3107	0.9174	0.053*
C15	−0.1061 (5)	0.2233 (3)	0.8910 (3)	0.0494 (10)
H15	−0.0461	0.1586	0.8906	0.059*
C16	−0.0145 (5)	0.3191 (3)	0.8780 (3)	0.0452 (9)
H16	0.1054	0.3184	0.8689	0.054*
C17	0.1985 (5)	0.5308 (3)	0.6978 (3)	0.0510 (10)
C18	0.2909 (6)	0.4405 (4)	0.6757 (4)	0.0650 (12)
H18	0.3386	0.3891	0.7288	0.078*
C19	0.3118 (7)	0.4269 (5)	0.5753 (4)	0.0785 (15)
H19	0.3684	0.3649	0.5631	0.094*
C20	0.2496 (7)	0.5043 (5)	0.4941 (5)	0.0835 (16)
H20	0.2678	0.4960	0.4272	0.100*
C21	0.1591 (7)	0.5951 (5)	0.5133 (4)	0.0792 (15)
H21	0.1146	0.6473	0.4596	0.095*
C22	0.1365 (6)	0.6065 (4)	0.6129 (4)	0.0609 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0292 (5)	0.0336 (5)	0.0692 (7)	0.0070 (4)	−0.0021 (4)	−0.0151 (4)
S2	0.0308 (5)	0.0362 (5)	0.0800 (8)	0.0050 (4)	−0.0071 (5)	−0.0173 (5)
O1	0.0437 (15)	0.0371 (14)	0.080 (2)	0.0118 (12)	−0.0007 (13)	−0.0210 (13)
O2	0.0355 (15)	0.0474 (16)	0.096 (2)	−0.0039 (12)	0.0047 (14)	−0.0152 (14)
O3	0.042 (2)	0.187 (5)	0.107 (3)	0.030 (3)	−0.0068 (19)	−0.025 (3)
O4	0.094 (3)	0.098 (3)	0.073 (2)	−0.037 (2)	−0.0075 (19)	−0.016 (2)
O5	0.0410 (16)	0.0427 (16)	0.114 (3)	−0.0023 (12)	−0.0067 (16)	−0.0272 (16)
O6	0.0389 (16)	0.0580 (18)	0.091 (2)	0.0156 (13)	−0.0159 (14)	−0.0204 (15)
O7	0.102 (3)	0.114 (3)	0.088 (3)	0.060 (3)	0.004 (2)	−0.005 (2)
O8	0.167 (5)	0.049 (2)	0.198 (5)	0.014 (3)	−0.043 (4)	−0.007 (3)
N1	0.047 (2)	0.0334 (18)	0.076 (3)	0.0107 (15)	−0.0029 (17)	−0.0165 (16)
N2	0.0327 (16)	0.0312 (16)	0.061 (2)	0.0069 (12)	−0.0074 (14)	−0.0149 (14)
N3	0.052 (3)	0.106 (4)	0.051 (2)	−0.006 (2)	−0.0016 (18)	−0.009 (2)
N4	0.0427 (19)	0.0346 (17)	0.064 (2)	−0.0025 (14)	−0.0061 (16)	−0.0116 (15)
N5	0.0337 (17)	0.0295 (16)	0.069 (2)	0.0076 (13)	−0.0044 (14)	−0.0143 (14)
N6	0.090 (4)	0.068 (3)	0.083 (3)	0.025 (3)	−0.012 (3)	0.001 (2)
C1	0.0348 (19)	0.0311 (18)	0.043 (2)	0.0036 (15)	−0.0001 (15)	−0.0084 (15)
C2	0.043 (2)	0.038 (2)	0.064 (3)	0.0032 (17)	−0.0134 (19)	−0.0195 (18)
C3	0.040 (2)	0.044 (2)	0.067 (3)	0.0144 (18)	−0.0130 (19)	−0.0144 (19)
C4	0.042 (2)	0.033 (2)	0.088 (3)	0.0000 (17)	−0.003 (2)	−0.023 (2)
C5	0.033 (2)	0.039 (2)	0.070 (3)	0.0034 (16)	−0.0053 (18)	−0.0173 (18)
C6	0.033 (2)	0.033 (2)	0.084 (3)	0.0124 (16)	−0.016 (2)	−0.0191 (19)
C7	0.050 (3)	0.073 (3)	0.106 (4)	0.008 (2)	−0.025 (3)	−0.033 (3)
C8	0.079 (4)	0.104 (5)	0.116 (5)	0.022 (3)	−0.053 (4)	−0.053 (4)
C9	0.109 (5)	0.093 (4)	0.082 (4)	0.051 (4)	−0.051 (4)	−0.049 (3)
C10	0.075 (3)	0.079 (3)	0.068 (3)	0.034 (3)	−0.019 (3)	−0.024 (3)
C11	0.047 (2)	0.057 (3)	0.061 (3)	0.017 (2)	−0.018 (2)	−0.022 (2)
C12	0.039 (2)	0.0328 (19)	0.046 (2)	0.0066 (15)	−0.0058 (16)	−0.0128 (16)
C13	0.032 (2)	0.037 (2)	0.064 (3)	0.0085 (15)	−0.0013 (17)	−0.0165 (17)
C14	0.034 (2)	0.041 (2)	0.059 (3)	0.0043 (16)	−0.0023 (17)	−0.0135 (18)
C15	0.044 (2)	0.031 (2)	0.075 (3)	0.0121 (17)	−0.0098 (19)	−0.0155 (18)
C16	0.0316 (19)	0.033 (2)	0.071 (3)	0.0094 (15)	−0.0041 (17)	−0.0143 (18)
C17	0.033 (2)	0.036 (2)	0.079 (3)	−0.0037 (16)	0.0024 (19)	−0.0073 (19)
C18	0.051 (3)	0.061 (3)	0.081 (4)	0.011 (2)	0.008 (2)	−0.018 (2)
C19	0.067 (3)	0.079 (4)	0.093 (4)	0.006 (3)	0.016 (3)	−0.034 (3)
C20	0.065 (3)	0.106 (5)	0.080 (4)	−0.015 (3)	0.018 (3)	−0.029 (3)
C21	0.061 (3)	0.077 (4)	0.089 (4)	−0.003 (3)	0.005 (3)	−0.004 (3)
C22	0.053 (3)	0.049 (3)	0.077 (3)	−0.003 (2)	0.004 (2)	−0.014 (2)

Geometric parameters (Å, º) top

S1—O2	1.459 (3)	C5—H5	0.9300
S1—O1	1.460 (3)	C6—C7	1.399 (6)
S1—N2	1.605 (3)	C6—C11	1.407 (6)
S1—C6	1.801 (5)	C7—C8	1.395 (8)
S2—O5	1.453 (3)	C7—H7	0.9300
S2—O6	1.455 (3)	C8—C9	1.384 (9)
S2—N5	1.606 (3)	C8—H8	0.9300
S2—C17	1.804 (5)	C9—C10	1.396 (8)
O3—N3	1.232 (5)	C9—H9	0.9300
O4—N3	1.237 (5)	C10—C11	1.397 (6)
O7—N6	1.217 (6)	C10—H10	0.9300
O8—N6	1.219 (6)	C12—C13	1.423 (5)
N1—C3	1.348 (5)	C12—C16	1.441 (5)
N1—C4	1.356 (5)	C13—C14	1.368 (5)
N1—H1A	0.88 (5)	C13—H13	0.9300
N2—C1	1.382 (4)	C14—H14	0.9300
N3—C11	1.501 (6)	C15—C16	1.377 (5)
N4—C15	1.346 (5)	C15—H15	0.9300
N4—C14	1.360 (5)	C16—H16	0.9300
N4—H4A	0.95 (4)	C17—C22	1.402 (6)
N5—C12	1.374 (4)	C17—C18	1.411 (6)
N6—C22	1.499 (6)	C18—C19	1.397 (7)
C1—C5	1.416 (5)	C18—H18	0.9300
C1—C2	1.427 (5)	C19—C20	1.380 (8)
C2—C3	1.376 (5)	C19—H19	0.9300
C2—H2	0.9300	C20—C21	1.396 (7)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.387 (5)	C21—C22	1.378 (7)
C4—H4	0.9300	C21—H21	0.9300

O2—S1—O1	116.20 (17)	C6—C7—H7	119.3
O2—S1—N2	115.50 (16)	C9—C8—C7	120.7 (5)
O1—S1—N2	106.12 (15)	C9—C8—H8	119.6
O2—S1—C6	105.37 (18)	C7—C8—H8	119.6
O1—S1—C6	106.63 (16)	C8—C9—C10	120.1 (5)
N2—S1—C6	106.27 (16)	C8—C9—H9	120.0
O5—S2—O6	116.83 (17)	C10—C9—H9	120.0
O5—S2—N5	106.34 (16)	C9—C10—C11	118.1 (5)
O6—S2—N5	114.96 (17)	C9—C10—H10	121.0
O5—S2—C17	106.20 (18)	C11—C10—H10	121.0
O6—S2—C17	106.00 (18)	C10—C11—C6	123.5 (4)
N5—S2—C17	105.63 (17)	C10—C11—N3	114.9 (4)
C3—N1—C4	120.7 (3)	C6—C11—N3	121.6 (4)
C3—N1—H1A	122 (3)	N5—C12—C13	118.1 (3)
C4—N1—H1A	117 (3)	N5—C12—C16	126.5 (3)
C1—N2—S1	122.7 (2)	C13—C12—C16	115.4 (3)
O3—N3—O4	125.2 (5)	C14—C13—C12	121.7 (3)
O3—N3—C11	117.7 (5)	C14—C13—H13	119.2
O4—N3—C11	117.1 (4)	C12—C13—H13	119.2
C15—N4—C14	120.3 (3)	N4—C14—C13	120.7 (3)
C15—N4—H4A	122 (2)	N4—C14—H14	119.6
C14—N4—H4A	117 (2)	C13—C14—H14	119.6
C12—N5—S2	122.8 (2)	N4—C15—C16	122.0 (3)
O7—N6—O8	124.3 (5)	N4—C15—H15	119.0
O7—N6—C22	117.2 (5)	C16—C15—H15	119.0
O8—N6—C22	118.4 (5)	C15—C16—C12	119.9 (3)
N2—C1—C5	127.5 (3)	C15—C16—H16	120.1
N2—C1—C2	116.3 (3)	C12—C16—H16	120.1
C5—C1—C2	116.3 (3)	C22—C17—C18	115.8 (4)
C3—C2—C1	121.0 (3)	C22—C17—S2	123.5 (3)
C3—C2—H2	119.5	C18—C17—S2	120.7 (3)
C1—C2—H2	119.5	C19—C18—C17	121.1 (4)
N1—C3—C2	120.7 (4)	C19—C18—H18	119.4
N1—C3—H3	119.6	C17—C18—H18	119.4
C2—C3—H3	119.6	C20—C19—C18	120.8 (5)
N1—C4—C5	121.3 (3)	C20—C19—H19	119.6
N1—C4—H4	119.4	C18—C19—H19	119.6
C5—C4—H4	119.4	C19—C20—C21	119.4 (5)
C4—C5—C1	120.0 (3)	C19—C20—H20	120.3
C4—C5—H5	120.0	C21—C20—H20	120.3
C1—C5—H5	120.0	C22—C21—C20	119.2 (5)
C7—C6—C11	116.2 (4)	C22—C21—H21	120.4
C7—C6—S1	119.4 (4)	C20—C21—H21	120.4
C11—C6—S1	124.3 (3)	C21—C22—C17	123.6 (4)
C8—C7—C6	121.4 (5)	C21—C22—N6	115.2 (4)
C8—C7—H7	119.3	C17—C22—N6	121.2 (4)

O2—S1—N2—C1	46.5 (3)	O4—N3—C11—C10	105.2 (5)
O1—S1—N2—C1	176.9 (3)	O3—N3—C11—C6	108.8 (5)
C6—S1—N2—C1	−69.9 (3)	O4—N3—C11—C6	−73.6 (5)
O5—S2—N5—C12	−178.8 (3)	S2—N5—C12—C13	−172.5 (3)
O6—S2—N5—C12	−47.9 (4)	S2—N5—C12—C16	7.1 (5)
C17—S2—N5—C12	68.6 (3)	N5—C12—C13—C14	176.4 (3)
S1—N2—C1—C5	−4.5 (5)	C16—C12—C13—C14	−3.2 (5)
S1—N2—C1—C2	175.0 (3)	C15—N4—C14—C13	0.5 (6)
N2—C1—C2—C3	180.0 (3)	C12—C13—C14—N4	2.0 (6)
C5—C1—C2—C3	−0.5 (6)	C14—N4—C15—C16	−1.5 (6)
C4—N1—C3—C2	1.7 (6)	N4—C15—C16—C12	0.1 (6)
C1—C2—C3—N1	−1.0 (6)	N5—C12—C16—C15	−177.3 (4)
C3—N1—C4—C5	−0.9 (6)	C13—C12—C16—C15	2.2 (5)
N1—C4—C5—C1	−0.6 (6)	O5—S2—C17—C22	−40.9 (4)
N2—C1—C5—C4	−179.3 (4)	O6—S2—C17—C22	−165.8 (3)
C2—C1—C5—C4	1.2 (5)	N5—S2—C17—C22	71.8 (4)
O2—S1—C6—C7	22.1 (4)	O5—S2—C17—C18	137.9 (3)
O1—S1—C6—C7	−101.9 (3)	O6—S2—C17—C18	13.0 (4)
N2—S1—C6—C7	145.2 (3)	N5—S2—C17—C18	−109.4 (3)
O2—S1—C6—C11	−161.2 (3)	C22—C17—C18—C19	−2.3 (6)
O1—S1—C6—C11	74.7 (3)	S2—C17—C18—C19	178.8 (3)
N2—S1—C6—C11	−38.2 (3)	C17—C18—C19—C20	3.1 (7)
C11—C6—C7—C8	−0.4 (6)	C18—C19—C20—C21	−2.4 (8)
S1—C6—C7—C8	176.5 (4)	C19—C20—C21—C22	1.1 (8)
C6—C7—C8—C9	2.5 (8)	C20—C21—C22—C17	−0.6 (7)
C7—C8—C9—C10	−2.7 (8)	C20—C21—C22—N6	−178.2 (5)
C8—C9—C10—C11	0.8 (7)	C18—C17—C22—C21	1.1 (6)
C9—C10—C11—C6	1.3 (6)	S2—C17—C22—C21	−180.0 (4)
C9—C10—C11—N3	−177.5 (4)	C18—C17—C22—N6	178.6 (4)
C7—C6—C11—C10	−1.5 (6)	S2—C17—C22—N6	−2.5 (6)
S1—C6—C11—C10	−178.3 (3)	O7—N6—C22—C21	98.9 (5)
C7—C6—C11—N3	177.2 (4)	O8—N6—C22—C21	−78.3 (6)
S1—C6—C11—N3	0.5 (6)	O7—N6—C22—C17	−78.8 (6)
O3—N3—C11—C10	−72.4 (5)	O8—N6—C22—C17	104.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.95 (4)	2.67 (4)	3.215 (4)	117 (3)
N4—H4A···N2ⁱ	0.95 (4)	2.08 (4)	2.969 (4)	155 (3)
N1—H1A···N5ⁱⁱ	0.88 (5)	2.02 (5)	2.898 (4)	172 (4)
C14—H14···O1ⁱ	0.93	2.54	3.140 (5)	122
C14—H14···O6ⁱⁱⁱ	0.93	2.58	3.249 (5)	130
C16—H16···O1^iv	0.93	2.54	3.265 (5)	135

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

Experimental details

Crystal data
Chemical formula	C₁₁H₉N₃O₄S
M_r	279.27
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.768 (3), 12.570 (5), 13.436 (5)
α, β, γ (°)	75.534 (7), 85.400 (7), 88.741 (6)
V (Å³)	1266.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.924, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	6351, 4357, 2918
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.174, 1.02
No. of reflections	4357
No. of parameters	349
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.95 (4)	2.67 (4)	3.215 (4)	117 (3)
N4—H4A···N2ⁱ	0.95 (4)	2.08 (4)	2.969 (4)	155 (3)
N1—H1A···N5ⁱⁱ	0.88 (5)	2.02 (5)	2.898 (4)	172 (4)
C14—H14···O1ⁱ	0.93	2.54	3.140 (5)	122
C14—H14···O6ⁱⁱⁱ	0.93	2.58	3.249 (5)	130
C16—H16···O1^iv	0.93	2.54	3.265 (5)	135

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

References

Amendola, V., Boiocchi, M., Fabbrizzi, L. & Palchetti, A. (2005). Chem. Eur. J. 11, 120–127. Web of Science CSD CrossRef Google Scholar
Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lindley, P. F., Mahmoud, M. M., Dodd, C., Smith, C. H., Boyd, G. V. & Norris, T. (1977). Acta Cryst. B33, 2160–2164. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Schaumann, E., Rohr, A., Sieveking, S. & Walter, W. (1975). Angew. Chem. Int. Ed. Engl. 14, 493. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Yu, H.-J., Chen, J.-Z., Simpson, J., Li, J.-S. & Bai, G.-Y. (2007). Acta Cryst. E63, o3720. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o204

https://doi.org/10.1107/S1600536807064410

Open

access