Sulfachloro­pyridazine

In the title compound, 4-amino-N-(6-chloro-3-pyridazin­yl)­benzene­sulfonamide, C₁₀H₉ClN₄O₂S, the pyridazine ring and the benzene ring form a distorted V configuration, with a dihedral angle of 82.86 (6)°. The crystal packing is stabilized by π–π stacking inter­actions between the pyridazine rings and inter­molecular N—H...O, C—H...O and C—H...N hydrogen bonds, linking the mol­ecules into a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.043
• wR factor = 0.100
• Data-to-parameter ratio = 15.5

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku & Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL.

4-amino-N-(6-chloro-3-pyridazinyl)-benzenesulfnamide

Crystal data

C10H9ClN4O2S	F(000) = 584
Mr = 284.72	Dx = 1.583 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 5140 reflections
a = 5.549 (2) Å	θ = 3.2–27.5°
b = 17.097 (7) Å	µ = 0.49 mm^−1
c = 12.606 (5) Å	T = 193 K
β = 92.647 (10)°	Block, orange–yellow
V = 1194.6 (8) Å^3	0.39 × 0.29 × 0.20 mm
Z = 4

Data collection

Rigaku Mercury diffractometer	2731 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −7→6
Absorption correction: multi-scan (Jacobson, 1998)	k = −22→22
Tmin = 0.831, Tmax = 0.908	l = −16→16
13214 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.8089P] where P = (Fo^2 + 2Fc^2)/3
2731 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.92970 (12)	0.36074 (4)	−0.04892 (5)	0.0572 (2)
S1	0.74003 (9)	0.58960 (3)	0.39696 (4)	0.02771 (14)
O1	0.4973 (3)	0.56101 (9)	0.38760 (11)	0.0344 (3)
O2	0.8490 (3)	0.60453 (9)	0.50034 (11)	0.0376 (4)
N1	0.9188 (3)	0.52263 (10)	0.34928 (14)	0.0316 (4)
N2	1.1033 (3)	0.45952 (12)	0.21781 (15)	0.0411 (4)
N3	1.1069 (3)	0.42074 (13)	0.12490 (16)	0.0454 (5)
N4	0.8543 (5)	0.85615 (12)	0.11039 (19)	0.0468 (5)
C1	0.8962 (3)	0.48782 (11)	0.24929 (15)	0.0276 (4)
C2	0.9057 (4)	0.41215 (13)	0.06822 (17)	0.0351 (5)
C3	0.6829 (4)	0.44004 (13)	0.09740 (17)	0.0344 (4)
H3	0.5407	0.4318	0.0540	0.041*
C4	0.6774 (3)	0.47963 (12)	0.19073 (16)	0.0321 (4)
H4	0.5315	0.5008	0.2151	0.039*
C5	0.7641 (3)	0.67165 (11)	0.31731 (15)	0.0269 (4)
C6	0.5842 (4)	0.68930 (12)	0.24047 (16)	0.0311 (4)
H6	0.4422	0.6583	0.2344	0.037*
C7	0.6123 (4)	0.75166 (12)	0.17335 (17)	0.0346 (5)
H7	0.4875	0.7642	0.1220	0.042*
C8	0.8222 (4)	0.79682 (12)	0.17977 (17)	0.0333 (4)
C9	1.0002 (4)	0.77888 (13)	0.25887 (19)	0.0386 (5)
H9	1.1418	0.8101	0.2656	0.046*
C10	0.9726 (4)	0.71698 (12)	0.32651 (17)	0.0351 (5)
H10	1.0949	0.7051	0.3793	0.042*
H1	1.052 (5)	0.5242 (15)	0.373 (2)	0.042 (7)*
H4A	0.991 (6)	0.8796 (17)	0.117 (2)	0.057 (9)*
H4B	0.738 (6)	0.8706 (18)	0.070 (2)	0.059 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0468 (3)	0.0782 (5)	0.0469 (4)	0.0020 (3)	0.0059 (3)	−0.0283 (3)
S1	0.0302 (3)	0.0293 (2)	0.0235 (2)	0.00260 (18)	0.00008 (18)	0.00077 (17)
O1	0.0324 (7)	0.0381 (8)	0.0331 (7)	−0.0035 (6)	0.0047 (6)	0.0023 (6)
O2	0.0446 (9)	0.0438 (8)	0.0238 (7)	0.0041 (7)	−0.0050 (6)	−0.0020 (6)
N1	0.0301 (9)	0.0311 (9)	0.0328 (9)	0.0067 (7)	−0.0059 (7)	−0.0027 (7)
N2	0.0250 (8)	0.0543 (11)	0.0437 (10)	0.0050 (8)	−0.0014 (7)	−0.0142 (9)
N3	0.0279 (9)	0.0630 (13)	0.0451 (11)	0.0064 (9)	0.0006 (8)	−0.0184 (10)
N4	0.0506 (13)	0.0385 (11)	0.0523 (13)	0.0004 (10)	0.0124 (11)	0.0133 (9)
C1	0.0278 (9)	0.0250 (9)	0.0300 (9)	0.0024 (7)	0.0005 (7)	0.0015 (7)
C2	0.0301 (10)	0.0415 (11)	0.0340 (10)	−0.0005 (9)	0.0038 (8)	−0.0075 (9)
C3	0.0250 (10)	0.0421 (11)	0.0358 (11)	−0.0010 (8)	−0.0025 (8)	−0.0030 (9)
C4	0.0224 (9)	0.0380 (11)	0.0359 (11)	0.0035 (8)	0.0007 (8)	−0.0026 (8)
C5	0.0263 (9)	0.0269 (9)	0.0275 (9)	0.0029 (7)	0.0016 (7)	0.0005 (7)
C6	0.0262 (9)	0.0336 (10)	0.0334 (10)	0.0019 (8)	−0.0010 (8)	0.0030 (8)
C7	0.0336 (10)	0.0366 (11)	0.0334 (10)	0.0057 (9)	−0.0013 (8)	0.0046 (8)
C8	0.0366 (11)	0.0283 (10)	0.0358 (10)	0.0058 (8)	0.0114 (8)	0.0016 (8)
C9	0.0311 (10)	0.0326 (10)	0.0521 (13)	−0.0043 (9)	0.0028 (9)	0.0006 (9)
C10	0.0283 (10)	0.0355 (11)	0.0409 (11)	0.0002 (8)	−0.0045 (8)	0.0010 (9)

Geometric parameters (Å, º)

Cl1—C2	1.729 (2)	C2—C3	1.390 (3)
S1—O1	1.4327 (16)	C3—C4	1.359 (3)
S1—O2	1.4339 (15)	C3—H3	0.9500
S1—N1	1.6467 (18)	C4—H4	0.9500
S1—C5	1.734 (2)	C5—C6	1.391 (3)
N1—C1	1.394 (3)	C5—C10	1.393 (3)
N1—H1	0.78 (3)	C6—C7	1.374 (3)
N2—C1	1.324 (3)	C6—H6	0.9500
N2—N3	1.347 (3)	C7—C8	1.397 (3)
N3—C2	1.306 (3)	C7—H7	0.9500
N4—C8	1.356 (3)	C8—C9	1.405 (3)
N4—H4A	0.86 (3)	C9—C10	1.372 (3)
N4—H4B	0.84 (3)	C9—H9	0.9500
C1—C4	1.399 (3)	C10—H10	0.9500
O1—S1—O2	119.40 (9)	C2—C3—H3	121.4
O1—S1—N1	108.22 (10)	C3—C4—C1	116.93 (18)
O2—S1—N1	102.70 (9)	C3—C4—H4	121.5
O1—S1—C5	109.00 (9)	C1—C4—H4	121.5
O2—S1—C5	109.99 (10)	C6—C5—C10	120.24 (18)
N1—S1—C5	106.70 (9)	C6—C5—S1	120.44 (15)
C1—N1—S1	126.60 (14)	C10—C5—S1	119.20 (15)
C1—N1—H1	113.7 (19)	C7—C6—C5	119.92 (19)
S1—N1—H1	114.3 (19)	C7—C6—H6	120.0
C1—N2—N3	119.23 (17)	C5—C6—H6	120.0
C2—N3—N2	119.00 (18)	C6—C7—C8	120.73 (19)
C8—N4—H4A	115 (2)	C6—C7—H7	119.6
C8—N4—H4B	119 (2)	C8—C7—H7	119.6
H4A—N4—H4B	125 (3)	N4—C8—C7	120.7 (2)
N2—C1—N1	112.58 (17)	N4—C8—C9	120.8 (2)
N2—C1—C4	123.32 (19)	C7—C8—C9	118.54 (19)
N1—C1—C4	124.01 (18)	C10—C9—C8	121.0 (2)
N3—C2—C3	124.4 (2)	C10—C9—H9	119.5
N3—C2—Cl1	115.28 (16)	C8—C9—H9	119.5
C3—C2—Cl1	120.32 (16)	C9—C10—C5	119.58 (19)
C4—C3—C2	117.13 (19)	C9—C10—H10	120.2
C4—C3—H3	121.4	C5—C10—H10	120.2
O1—S1—N1—C1	53.70 (19)	O2—S1—C5—C6	−147.01 (16)
O2—S1—N1—C1	−179.15 (17)	N1—S1—C5—C6	102.30 (18)
C5—S1—N1—C1	−63.5 (2)	O1—S1—C5—C10	169.67 (16)
C1—N2—N3—C2	0.1 (3)	O2—S1—C5—C10	37.01 (19)
N3—N2—C1—N1	176.75 (19)	N1—S1—C5—C10	−73.68 (18)
N3—N2—C1—C4	0.0 (3)	C10—C5—C6—C7	0.0 (3)
S1—N1—C1—N2	156.57 (17)	S1—C5—C6—C7	−175.91 (16)
S1—N1—C1—C4	−26.7 (3)	C5—C6—C7—C8	1.3 (3)
N2—N3—C2—C3	−0.5 (4)	C6—C7—C8—N4	177.0 (2)
N2—N3—C2—Cl1	−179.42 (18)	C6—C7—C8—C9	−2.3 (3)
N3—C2—C3—C4	0.9 (4)	N4—C8—C9—C10	−177.4 (2)
Cl1—C2—C3—C4	179.71 (17)	C7—C8—C9—C10	1.9 (3)
C2—C3—C4—C1	−0.7 (3)	C8—C9—C10—C5	−0.6 (3)
N2—C1—C4—C3	0.3 (3)	C6—C5—C10—C9	−0.4 (3)
N1—C1—C4—C3	−176.03 (19)	S1—C5—C10—C9	175.58 (17)
O1—S1—C5—C6	−14.35 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2^i	0.86 (3)	2.54 (3)	3.204 (3)	135 (3)
N4—H4A···O2^i	0.86 (3)	2.54 (3)	3.204 (3)	135 (3)
N1—H1···O1^ii	0.78 (3)	2.55 (3)	3.290 (3)	158 (2)
C4—H4···N2^iii	0.95	2.48	3.237 (3)	137
C4—H4···O1	0.95	2.42	3.053 (3)	124
C3—H3···N3^iii	0.95	2.61	3.248 (3)	125

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x−1, y, z.