N-(6-Chloro­pyridazin-3-yl)-4-methyl­benzene­sulfonamide

In the title compound, C₁₁H₁₀ClN₃O₂S, the pyridazine ring and the benzene ring adopt a distorted V configuration, forming a dihedral angle of 73.79 (11)°. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds. Weak intra­molecular C—H...O and inter­molecular C—H...O and C—H...N inter­actions are also observed. The mol­ecules are linked into one-dimensional chains along the c axis and these chains are inter­connected, forming a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.159
• Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C8     -   C11    ...       1.37 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamide

Crystal data

C11H10ClN3O2S	F(000) = 1168
Mr = 283.74	Dx = 1.563 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2965 reflections
a = 29.8577 (4) Å	θ = 1.5–30.0°
b = 5.6198 (1) Å	µ = 0.49 mm^−1
c = 16.1140 (2) Å	T = 297 K
β = 116.892 (1)°	Rod, colorless or light yellow?
V = 2411.45 (7) Å^3	0.50 × 0.33 × 0.27 mm
Z = 8

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3507 independent reflections
Radiation source: fine-focus sealed tube	2965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.5°
ω scans	h = −42→41
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.792, Tmax = 0.881	l = −22→22
19119 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0966P)^2 + 1.8315P] where P = (Fo^2 + 2Fc^2)/3
3507 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
S1	0.149188 (17)	0.16291 (9)	0.34156 (3)	0.04022 (16)
Cl1	−0.08085 (2)	0.45853 (12)	−0.02156 (5)	0.0659 (2)
O1	0.13103 (6)	−0.0735 (3)	0.33793 (11)	0.0522 (4)
O2	0.18807 (6)	0.2488 (3)	0.42799 (10)	0.0580 (4)
N1	0.10183 (6)	0.3493 (3)	0.31781 (12)	0.0444 (4)
N2	0.04107 (8)	0.5648 (3)	0.20208 (16)	0.0591 (5)
N3	−0.00186 (8)	0.5919 (3)	0.12367 (17)	0.0638 (6)
C1	0.05824 (7)	0.3496 (3)	0.23199 (13)	0.0376 (4)
C2	0.03368 (8)	0.1437 (3)	0.18517 (15)	0.0457 (4)
H2A	0.0461	−0.0068	0.2080	0.055*
C3	−0.00945 (8)	0.1727 (4)	0.10440 (16)	0.0478 (5)
H3A	−0.0272	0.0431	0.0689	0.057*
C4	−0.02557 (7)	0.4030 (4)	0.07782 (15)	0.0443 (4)
C5	0.16706 (6)	0.1989 (3)	0.25361 (12)	0.0347 (3)
C6	0.19286 (7)	0.4054 (3)	0.25216 (14)	0.0397 (4)
H6A	0.2003	0.5210	0.2978	0.048*
C7	0.20707 (7)	0.4362 (3)	0.18292 (15)	0.0416 (4)
H7A	0.2243	0.5734	0.1821	0.050*
C8	0.19603 (7)	0.2638 (3)	0.11340 (13)	0.0403 (4)
C9	0.16950 (8)	0.0594 (4)	0.11517 (14)	0.0448 (4)
H9A	0.1616	−0.0556	0.0692	0.054*
C10	0.15498 (7)	0.0274 (3)	0.18414 (14)	0.0399 (4)
H10A	0.1372	−0.1080	0.1845	0.048*
C11	0.21237 (10)	0.2905 (4)	0.04729 (16)	0.0519 (5)
H11A	0.1847	0.2684	−0.0133	0.078*
H11B	0.2379	0.1745	0.0571	0.078*
H11C	0.2260	0.4473	0.0516	0.078*
H1N1	0.1152 (12)	0.504 (6)	0.346 (2)	0.070 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0347 (2)	0.0469 (3)	0.0320 (2)	0.00104 (17)	0.00893 (18)	0.00158 (16)
Cl1	0.0454 (3)	0.0634 (4)	0.0645 (4)	0.0029 (2)	0.0032 (3)	0.0166 (3)
O1	0.0512 (8)	0.0496 (9)	0.0512 (8)	−0.0010 (7)	0.0190 (7)	0.0123 (6)
O2	0.0456 (8)	0.0790 (12)	0.0333 (7)	−0.0017 (8)	0.0036 (6)	−0.0045 (7)
N1	0.0372 (8)	0.0498 (10)	0.0432 (8)	0.0009 (7)	0.0155 (7)	−0.0108 (7)
N2	0.0507 (10)	0.0320 (8)	0.0713 (13)	−0.0013 (7)	0.0071 (9)	−0.0063 (8)
N3	0.0501 (10)	0.0324 (9)	0.0822 (15)	0.0024 (7)	0.0064 (10)	0.0037 (9)
C1	0.0333 (8)	0.0346 (8)	0.0438 (9)	−0.0003 (6)	0.0166 (7)	−0.0041 (7)
C2	0.0417 (10)	0.0287 (8)	0.0536 (11)	0.0015 (7)	0.0100 (8)	0.0009 (7)
C3	0.0430 (10)	0.0330 (9)	0.0535 (11)	−0.0022 (7)	0.0095 (9)	−0.0014 (7)
C4	0.0354 (8)	0.0388 (9)	0.0516 (11)	0.0015 (7)	0.0134 (8)	0.0058 (8)
C5	0.0297 (7)	0.0331 (8)	0.0354 (8)	0.0018 (6)	0.0096 (6)	−0.0009 (6)
C6	0.0362 (8)	0.0325 (8)	0.0456 (9)	−0.0029 (6)	0.0144 (7)	−0.0084 (7)
C7	0.0376 (9)	0.0315 (8)	0.0525 (10)	−0.0020 (6)	0.0175 (8)	0.0001 (7)
C8	0.0387 (9)	0.0400 (9)	0.0400 (9)	0.0052 (7)	0.0159 (7)	0.0038 (7)
C9	0.0519 (11)	0.0382 (9)	0.0410 (9)	−0.0028 (8)	0.0181 (8)	−0.0080 (7)
C10	0.0407 (9)	0.0311 (8)	0.0427 (9)	−0.0030 (6)	0.0144 (7)	−0.0037 (6)
C11	0.0617 (13)	0.0549 (12)	0.0474 (11)	−0.0028 (10)	0.0321 (10)	0.0011 (9)

Geometric parameters (Å, º)

S1—O1	1.4258 (17)	C5—C10	1.395 (2)
S1—O2	1.4345 (15)	C5—C6	1.399 (2)
S1—N1	1.6592 (18)	C6—C7	1.372 (3)
S1—C5	1.7373 (19)	C6—H6A	0.9300
Cl1—C4	1.731 (2)	C7—C8	1.403 (3)
N1—C1	1.406 (2)	C7—H7A	0.9300
N1—H1N1	0.98 (3)	C8—C11	1.366 (3)
N2—C1	1.317 (3)	C8—C9	1.403 (3)
N2—N3	1.341 (3)	C9—C10	1.375 (3)
N3—C4	1.304 (3)	C9—H9A	0.9300
C1—C2	1.395 (3)	C10—H10A	0.9300
C2—C3	1.365 (3)	C11—H11A	0.9600
C2—H2A	0.9300	C11—H11B	0.9600
C3—C4	1.379 (3)	C11—H11C	0.9600
C3—H3A	0.9300
O1—S1—O2	118.62 (10)	C10—C5—S1	120.72 (14)
O1—S1—N1	108.07 (10)	C6—C5—S1	119.00 (14)
O2—S1—N1	104.04 (10)	C7—C6—C5	119.56 (17)
O1—S1—C5	109.04 (10)	C7—C6—H6A	120.2
O2—S1—C5	109.91 (10)	C5—C6—H6A	120.2
N1—S1—C5	106.41 (9)	C6—C7—C8	120.99 (17)
C1—N1—S1	122.74 (13)	C6—C7—H7A	119.5
C1—N1—H1N1	117 (2)	C8—C7—H7A	119.5
S1—N1—H1N1	109.1 (19)	C11—C8—C7	120.6 (2)
C1—N2—N3	119.82 (17)	C11—C8—C9	120.66 (19)
C4—N3—N2	118.95 (18)	C7—C8—C9	118.67 (18)
N2—C1—C2	122.79 (18)	C10—C9—C8	120.73 (18)
N2—C1—N1	113.28 (17)	C10—C9—H9A	119.6
C2—C1—N1	123.84 (17)	C8—C9—H9A	119.6
C3—C2—C1	117.06 (18)	C9—C10—C5	119.77 (18)
C3—C2—H2A	121.5	C9—C10—H10A	120.1
C1—C2—H2A	121.5	C5—C10—H10A	120.1
C2—C3—C4	117.03 (18)	C8—C11—H11A	109.5
C2—C3—H3A	121.5	C8—C11—H11B	109.5
C4—C3—H3A	121.5	H11A—C11—H11B	109.5
N3—C4—C3	124.3 (2)	C8—C11—H11C	109.5
N3—C4—Cl1	115.05 (16)	H11A—C11—H11C	109.5
C3—C4—Cl1	120.62 (16)	H11B—C11—H11C	109.5
C10—C5—C6	120.26 (17)
O1—S1—N1—C1	−62.25 (19)	O2—S1—C5—C10	142.30 (16)
O2—S1—N1—C1	170.81 (17)	N1—S1—C5—C10	−105.64 (16)
C5—S1—N1—C1	54.74 (18)	O1—S1—C5—C6	−170.73 (14)
C1—N2—N3—C4	−0.8 (4)	O2—S1—C5—C6	−39.13 (18)
N3—N2—C1—C2	0.3 (4)	N1—S1—C5—C6	72.93 (16)
N3—N2—C1—N1	−176.3 (2)	C10—C5—C6—C7	−1.3 (3)
S1—N1—C1—N2	−141.00 (19)	S1—C5—C6—C7	−179.83 (14)
S1—N1—C1—C2	42.5 (3)	C5—C6—C7—C8	0.1 (3)
N2—C1—C2—C3	1.1 (3)	C6—C7—C8—C11	−176.9 (2)
N1—C1—C2—C3	177.3 (2)	C6—C7—C8—C9	0.8 (3)
C1—C2—C3—C4	−1.8 (3)	C11—C8—C9—C10	177.1 (2)
N2—N3—C4—C3	−0.1 (4)	C7—C8—C9—C10	−0.6 (3)
N2—N3—C4—Cl1	179.3 (2)	C8—C9—C10—C5	−0.5 (3)
C2—C3—C4—N3	1.4 (4)	C6—C5—C10—C9	1.4 (3)
C2—C3—C4—Cl1	−177.98 (18)	S1—C5—C10—C9	180.00 (15)
O1—S1—C5—C10	10.70 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1^i	0.98 (3)	2.44 (3)	3.336 (2)	153 (2)
C2—H2A···O1	0.93	2.48	3.086 (3)	123
C2—H2A···N2^ii	0.93	2.41	3.264 (2)	152
C10—H10A···O1	0.93	2.57	2.929 (3)	104
C11—H11A···O1^iii	0.96	2.46	3.370 (3)	158
C11—H11C···O2^iv	0.96	2.48	3.109 (3)	123
C7—H7A···Cg1^v	0.93	2.81	3.467 (2)	128

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