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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015576/is6078sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015576/is6078Isup2.hkl
Contains datablock I

CCDC reference: 274449

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

checkCIF/PLATON results

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Computing details top

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 top
Crystal data top
C10H9ClN4O2SF(000) = 584
Mr = 284.72Dx = 1.583 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 5140 reflections
a = 5.549 (2) Åθ = 3.2–27.5°
b = 17.097 (7) ŵ = 0.49 mm1
c = 12.606 (5) ÅT = 193 K
β = 92.647 (10)°Block, orange–yellow
V = 1194.6 (8) Å30.39 × 0.29 × 0.20 mm
Z = 4
Data collection top
Rigaku Mercury
diffractometer
2731 independent reflections
Radiation source: fine-focus sealed tube2481 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 76
Absorption correction: multi-scan
(Jacobson, 1998)
k = 2222
Tmin = 0.831, Tmax = 0.908l = 1616
13214 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0397P)2 + 0.8089P]
where P = (Fo2 + 2Fc2)/3
2731 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.34 e Å3
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
xyzUiso*/Ueq
Cl10.92970 (12)0.36074 (4)0.04892 (5)0.0572 (2)
S10.74003 (9)0.58960 (3)0.39696 (4)0.02771 (14)
O10.4973 (3)0.56101 (9)0.38760 (11)0.0344 (3)
O20.8490 (3)0.60453 (9)0.50034 (11)0.0376 (4)
N10.9188 (3)0.52263 (10)0.34928 (14)0.0316 (4)
N21.1033 (3)0.45952 (12)0.21781 (15)0.0411 (4)
N31.1069 (3)0.42074 (13)0.12490 (16)0.0454 (5)
N40.8543 (5)0.85615 (12)0.11039 (19)0.0468 (5)
C10.8962 (3)0.48782 (11)0.24929 (15)0.0276 (4)
C20.9057 (4)0.41215 (13)0.06822 (17)0.0351 (5)
C30.6829 (4)0.44004 (13)0.09740 (17)0.0344 (4)
H30.54070.43180.05400.041*
C40.6774 (3)0.47963 (12)0.19073 (16)0.0321 (4)
H40.53150.50080.21510.039*
C50.7641 (3)0.67165 (11)0.31731 (15)0.0269 (4)
C60.5842 (4)0.68930 (12)0.24047 (16)0.0311 (4)
H60.44220.65830.23440.037*
C70.6123 (4)0.75166 (12)0.17335 (17)0.0346 (5)
H70.48750.76420.12200.042*
C80.8222 (4)0.79682 (12)0.17977 (17)0.0333 (4)
C91.0002 (4)0.77888 (13)0.25887 (19)0.0386 (5)
H91.14180.81010.26560.046*
C100.9726 (4)0.71698 (12)0.32651 (17)0.0351 (5)
H101.09490.70510.37930.042*
H11.052 (5)0.5242 (15)0.373 (2)0.042 (7)*
H4A0.991 (6)0.8796 (17)0.117 (2)0.057 (9)*
H4B0.738 (6)0.8706 (18)0.070 (2)0.059 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0468 (3)0.0782 (5)0.0469 (4)0.0020 (3)0.0059 (3)0.0283 (3)
S10.0302 (3)0.0293 (2)0.0235 (2)0.00260 (18)0.00008 (18)0.00077 (17)
O10.0324 (7)0.0381 (8)0.0331 (7)0.0035 (6)0.0047 (6)0.0023 (6)
O20.0446 (9)0.0438 (8)0.0238 (7)0.0041 (7)0.0050 (6)0.0020 (6)
N10.0301 (9)0.0311 (9)0.0328 (9)0.0067 (7)0.0059 (7)0.0027 (7)
N20.0250 (8)0.0543 (11)0.0437 (10)0.0050 (8)0.0014 (7)0.0142 (9)
N30.0279 (9)0.0630 (13)0.0451 (11)0.0064 (9)0.0006 (8)0.0184 (10)
N40.0506 (13)0.0385 (11)0.0523 (13)0.0004 (10)0.0124 (11)0.0133 (9)
C10.0278 (9)0.0250 (9)0.0300 (9)0.0024 (7)0.0005 (7)0.0015 (7)
C20.0301 (10)0.0415 (11)0.0340 (10)0.0005 (9)0.0038 (8)0.0075 (9)
C30.0250 (10)0.0421 (11)0.0358 (11)0.0010 (8)0.0025 (8)0.0030 (9)
C40.0224 (9)0.0380 (11)0.0359 (11)0.0035 (8)0.0007 (8)0.0026 (8)
C50.0263 (9)0.0269 (9)0.0275 (9)0.0029 (7)0.0016 (7)0.0005 (7)
C60.0262 (9)0.0336 (10)0.0334 (10)0.0019 (8)0.0010 (8)0.0030 (8)
C70.0336 (10)0.0366 (11)0.0334 (10)0.0057 (9)0.0013 (8)0.0046 (8)
C80.0366 (11)0.0283 (10)0.0358 (10)0.0058 (8)0.0114 (8)0.0016 (8)
C90.0311 (10)0.0326 (10)0.0521 (13)0.0043 (9)0.0028 (9)0.0006 (9)
C100.0283 (10)0.0355 (11)0.0409 (11)0.0002 (8)0.0045 (8)0.0010 (9)
Geometric parameters (Å, º) top
Cl1—C21.729 (2)C2—C31.390 (3)
S1—O11.4327 (16)C3—C41.359 (3)
S1—O21.4339 (15)C3—H30.9500
S1—N11.6467 (18)C4—H40.9500
S1—C51.734 (2)C5—C61.391 (3)
N1—C11.394 (3)C5—C101.393 (3)
N1—H10.78 (3)C6—C71.374 (3)
N2—C11.324 (3)C6—H60.9500
N2—N31.347 (3)C7—C81.397 (3)
N3—C21.306 (3)C7—H70.9500
N4—C81.356 (3)C8—C91.405 (3)
N4—H4A0.86 (3)C9—C101.372 (3)
N4—H4B0.84 (3)C9—H90.9500
C1—C41.399 (3)C10—H100.9500
O1—S1—O2119.40 (9)C2—C3—H3121.4
O1—S1—N1108.22 (10)C3—C4—C1116.93 (18)
O2—S1—N1102.70 (9)C3—C4—H4121.5
O1—S1—C5109.00 (9)C1—C4—H4121.5
O2—S1—C5109.99 (10)C6—C5—C10120.24 (18)
N1—S1—C5106.70 (9)C6—C5—S1120.44 (15)
C1—N1—S1126.60 (14)C10—C5—S1119.20 (15)
C1—N1—H1113.7 (19)C7—C6—C5119.92 (19)
S1—N1—H1114.3 (19)C7—C6—H6120.0
C1—N2—N3119.23 (17)C5—C6—H6120.0
C2—N3—N2119.00 (18)C6—C7—C8120.73 (19)
C8—N4—H4A115 (2)C6—C7—H7119.6
C8—N4—H4B119 (2)C8—C7—H7119.6
H4A—N4—H4B125 (3)N4—C8—C7120.7 (2)
N2—C1—N1112.58 (17)N4—C8—C9120.8 (2)
N2—C1—C4123.32 (19)C7—C8—C9118.54 (19)
N1—C1—C4124.01 (18)C10—C9—C8121.0 (2)
N3—C2—C3124.4 (2)C10—C9—H9119.5
N3—C2—Cl1115.28 (16)C8—C9—H9119.5
C3—C2—Cl1120.32 (16)C9—C10—C5119.58 (19)
C4—C3—C2117.13 (19)C9—C10—H10120.2
C4—C3—H3121.4C5—C10—H10120.2
O1—S1—N1—C153.70 (19)O2—S1—C5—C6147.01 (16)
O2—S1—N1—C1179.15 (17)N1—S1—C5—C6102.30 (18)
C5—S1—N1—C163.5 (2)O1—S1—C5—C10169.67 (16)
C1—N2—N3—C20.1 (3)O2—S1—C5—C1037.01 (19)
N3—N2—C1—N1176.75 (19)N1—S1—C5—C1073.68 (18)
N3—N2—C1—C40.0 (3)C10—C5—C6—C70.0 (3)
S1—N1—C1—N2156.57 (17)S1—C5—C6—C7175.91 (16)
S1—N1—C1—C426.7 (3)C5—C6—C7—C81.3 (3)
N2—N3—C2—C30.5 (4)C6—C7—C8—N4177.0 (2)
N2—N3—C2—Cl1179.42 (18)C6—C7—C8—C92.3 (3)
N3—C2—C3—C40.9 (4)N4—C8—C9—C10177.4 (2)
Cl1—C2—C3—C4179.71 (17)C7—C8—C9—C101.9 (3)
C2—C3—C4—C10.7 (3)C8—C9—C10—C50.6 (3)
N2—C1—C4—C30.3 (3)C6—C5—C10—C90.4 (3)
N1—C1—C4—C3176.03 (19)S1—C5—C10—C9175.58 (17)
O1—S1—C5—C614.35 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O2i0.86 (3)2.54 (3)3.204 (3)135 (3)
N4—H4A···O2i0.86 (3)2.54 (3)3.204 (3)135 (3)
N1—H1···O1ii0.78 (3)2.55 (3)3.290 (3)158 (2)
C4—H4···N2iii0.952.483.237 (3)137
C4—H4···O10.952.423.053 (3)124
C3—H3···N3iii0.952.613.248 (3)125
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x+1, y, z; (iii) x1, y, z.
 

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