6-Chloro-N-(pyridin-4-ylmeth-yl)pyridine-3-sulfonamide.

In the title sulfonamide derivative, C11H10ClN3O2S, the dihedral angle between the pyridine rings is 46.85 (12)°. The N atom of the chloro-pyridine ring is anti to the N-H bond. In the crystal, mol-ecules are linked through N-H⋯N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.

Related literature

For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶). For the anti­microbial activity of related compounds, see: Desai et al. (2013 ▶); Mohan et al. (2013 ▶). For the proliferation activity of these compounds, see: Renu et al. (2006 ▶), and for their tuberculostaic acitivity, see: Gobis et al. (2013 ▶).

Experimental

Crystal data

C11H10ClN3O2S

M = 283.73

Monoclinic,

a = 5.4140 (6) Å

b = 18.172 (2) Å

c = 12.9392 (15) Å

β = 92.388 (6)°

V = 1271.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.35 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.852, T max = 0.899

20929 measured reflections

2961 independent reflections

2185 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 0.82

2961 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813030523/wm2782sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030523/wm2782Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030523/wm2782Isup3.cml

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

C11H10ClN3O2S	Prism
Mr = 283.73	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Melting point: 492 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.4140 (6) Å	Cell parameters from 1103 reflections
b = 18.172 (2) Å	θ = 1.9–27.8°
c = 12.9392 (15) Å	µ = 0.46 mm−1
β = 92.388 (6)°	T = 293 K
V = 1271.9 (2) Å3	Prism, yellow
Z = 4	0.35 × 0.29 × 0.23 mm
F(000) = 584

Bruker APEXII CCD diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	2185 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 27.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.852, Tmax = 0.899	k = −23→23
20929 measured reflections	l = −13→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ2(Fo2) + (0.0847P)2 + 0.7427P] where P = (Fo2 + 2Fc2)/3
2961 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
HN2	0.486 (4)	0.3469 (13)	0.213 (2)	0.058 (7)*
S1	0.32655 (10)	0.44681 (3)	0.19440 (4)	0.0590 (2)
Cl1	1.10225 (15)	0.64661 (4)	0.41805 (6)	0.0911 (3)
C1	0.5418 (4)	0.50525 (11)	0.25986 (16)	0.0486 (4)
C7	0.6225 (4)	0.32076 (10)	0.00501 (15)	0.0474 (4)
N2	0.4712 (4)	0.37356 (11)	0.16614 (15)	0.0584 (5)
C3	0.8769 (4)	0.59143 (12)	0.35659 (18)	0.0600 (5)
N3	0.5621 (4)	0.22140 (11)	−0.15918 (16)	0.0692 (5)
C11	0.4300 (4)	0.27124 (12)	−0.00074 (17)	0.0571 (5)
H11	0.3157	0.2700	0.0509	0.068*
N1	0.8263 (5)	0.60509 (13)	0.2581 (2)	0.0899 (7)
O1	0.1498 (3)	0.42543 (11)	0.26714 (16)	0.0804 (5)
O2	0.2501 (4)	0.48324 (12)	0.10098 (16)	0.0912 (6)
C10	0.4071 (4)	0.22353 (13)	−0.08329 (19)	0.0653 (6)
H10	0.2746	0.1909	−0.0856	0.078*
C5	0.6049 (6)	0.49344 (15)	0.36172 (19)	0.0785 (8)
H5	0.5314	0.4553	0.3973	0.094*
C2	0.6559 (6)	0.56102 (15)	0.2099 (2)	0.0822 (8)
H2	0.6153	0.5691	0.1402	0.099*
C8	0.7862 (5)	0.31869 (14)	−0.0734 (2)	0.0676 (6)
H8	0.9200	0.3508	−0.0731	0.081*
C6	0.6641 (4)	0.37509 (14)	0.09095 (17)	0.0635 (6)
H6A	0.8220	0.3648	0.1262	0.076*
H6B	0.6725	0.4241	0.0617	0.076*
C4	0.7741 (6)	0.53707 (15)	0.41083 (18)	0.0797 (8)
H4	0.8183	0.5298	0.4803	0.096*
C9	0.7497 (5)	0.26847 (16)	−0.1525 (2)	0.0805 (8)
H9	0.8635	0.2675	−0.2044	0.097*

	U11	U22	U33	U12	U13	U23
S1	0.0487 (3)	0.0671 (4)	0.0603 (4)	−0.0063 (2)	−0.0084 (2)	0.0061 (3)
Cl1	0.0924 (5)	0.0868 (5)	0.0934 (5)	−0.0227 (4)	−0.0072 (4)	−0.0295 (4)
C1	0.0463 (10)	0.0461 (10)	0.0534 (11)	0.0038 (8)	0.0016 (8)	0.0003 (8)
C7	0.0480 (10)	0.0485 (10)	0.0454 (10)	0.0020 (8)	−0.0032 (8)	0.0064 (8)
N2	0.0767 (12)	0.0571 (10)	0.0413 (10)	−0.0150 (9)	0.0034 (8)	0.0012 (8)
C3	0.0623 (13)	0.0550 (12)	0.0626 (14)	−0.0032 (10)	0.0027 (10)	−0.0153 (10)
N3	0.0808 (13)	0.0633 (11)	0.0640 (12)	0.0020 (10)	0.0095 (10)	−0.0132 (9)
C11	0.0542 (11)	0.0622 (12)	0.0554 (12)	−0.0072 (10)	0.0088 (9)	−0.0077 (10)
N1	0.1045 (18)	0.0783 (14)	0.0853 (17)	−0.0339 (13)	−0.0122 (14)	0.0155 (12)
O1	0.0526 (9)	0.0965 (13)	0.0928 (13)	−0.0144 (9)	0.0127 (9)	−0.0050 (11)
O2	0.0814 (12)	0.1002 (14)	0.0883 (14)	−0.0074 (10)	−0.0385 (11)	0.0283 (11)
C10	0.0620 (13)	0.0641 (13)	0.0700 (15)	−0.0071 (11)	0.0051 (11)	−0.0144 (11)
C5	0.106 (2)	0.0773 (16)	0.0522 (14)	−0.0350 (15)	0.0037 (13)	0.0053 (12)
C2	0.098 (2)	0.0758 (16)	0.0713 (16)	−0.0242 (14)	−0.0187 (15)	0.0251 (13)
C8	0.0635 (14)	0.0694 (14)	0.0710 (15)	−0.0096 (11)	0.0158 (12)	−0.0021 (12)
C6	0.0645 (13)	0.0728 (14)	0.0532 (12)	−0.0219 (11)	0.0026 (10)	−0.0049 (11)
C4	0.111 (2)	0.0838 (17)	0.0432 (12)	−0.0313 (15)	−0.0079 (13)	−0.0001 (11)
C9	0.0896 (19)	0.0863 (18)	0.0678 (16)	−0.0030 (15)	0.0309 (14)	−0.0107 (14)

S1—O1	1.4238 (19)	N3—C9	1.328 (3)
S1—O2	1.4244 (18)	C11—C10	1.377 (3)
S1—N2	1.595 (2)	C11—H11	0.9300
S1—C1	1.767 (2)	N1—C2	1.354 (3)
Cl1—C3	1.745 (2)	C10—H10	0.9300
C1—C2	1.364 (3)	C5—C4	1.350 (3)
C1—C5	1.365 (3)	C5—H5	0.9300
C7—C11	1.376 (3)	C2—H2	0.9300
C7—C8	1.375 (3)	C8—C9	1.379 (4)
C7—C6	1.497 (3)	C8—H8	0.9300
N2—C6	1.457 (3)	C6—H6A	0.9700
N2—HN2	0.78 (3)	C6—H6B	0.9700
C3—N1	1.316 (3)	C4—H4	0.9300
C3—C4	1.346 (3)	C9—H9	0.9300
N3—C10	1.318 (3)
O1—S1—O2	120.54 (13)	N3—C10—H10	118.1
O1—S1—N2	105.88 (11)	C11—C10—H10	118.1
O2—S1—N2	108.75 (13)	C4—C5—C1	120.0 (2)
O1—S1—C1	107.16 (11)	C4—C5—H5	120.0
O2—S1—C1	106.87 (11)	C1—C5—H5	120.0
N2—S1—C1	106.94 (10)	N1—C2—C1	122.3 (2)
C2—C1—C5	118.3 (2)	N1—C2—H2	118.9
C2—C1—S1	121.47 (18)	C1—C2—H2	118.9
C5—C1—S1	120.14 (17)	C7—C8—C9	119.2 (2)
C11—C7—C8	116.9 (2)	C7—C8—H8	120.4
C11—C7—C6	124.15 (19)	C9—C8—H8	120.4
C8—C7—C6	118.97 (19)	N2—C6—C7	113.18 (17)
C6—N2—S1	120.65 (17)	N2—C6—H6A	108.9
C6—N2—HN2	118.6 (19)	C7—C6—H6A	108.9
S1—N2—HN2	112.0 (18)	N2—C6—H6B	108.9
N1—C3—C4	124.7 (2)	C7—C6—H6B	108.9
N1—C3—Cl1	116.52 (19)	H6A—C6—H6B	107.8
C4—C3—Cl1	118.74 (19)	C3—C4—C5	118.2 (2)
C10—N3—C9	116.2 (2)	C3—C4—H4	120.9
C7—C11—C10	119.8 (2)	C5—C4—H4	120.9
C7—C11—H11	120.1	N3—C9—C8	124.1 (2)
C10—C11—H11	120.1	N3—C9—H9	118.0
C3—N1—C2	116.4 (2)	C8—C9—H9	118.0
N3—C10—C11	123.8 (2)
O1—S1—C1—C2	−148.2 (2)	C2—C1—C5—C4	0.9 (4)
O2—S1—C1—C2	−17.7 (3)	S1—C1—C5—C4	178.3 (2)
N2—S1—C1—C2	98.7 (2)	C3—N1—C2—C1	0.0 (5)
O1—S1—C1—C5	34.4 (2)	C5—C1—C2—N1	−0.7 (5)
O2—S1—C1—C5	164.9 (2)	S1—C1—C2—N1	−178.2 (2)
N2—S1—C1—C5	−78.7 (2)	C11—C7—C8—C9	0.3 (3)
O1—S1—N2—C6	178.59 (17)	C6—C7—C8—C9	179.6 (2)
O2—S1—N2—C6	47.7 (2)	S1—N2—C6—C7	−125.57 (19)
C1—S1—N2—C6	−67.37 (19)	C11—C7—C6—N2	−3.3 (3)
C8—C7—C11—C10	−0.9 (3)	C8—C7—C6—N2	177.4 (2)
C6—C7—C11—C10	179.8 (2)	N1—C3—C4—C5	−0.6 (5)
C4—C3—N1—C2	0.7 (5)	Cl1—C3—C4—C5	−178.2 (2)
Cl1—C3—N1—C2	178.4 (2)	C1—C5—C4—C3	−0.2 (5)
C9—N3—C10—C11	0.5 (4)	C10—N3—C9—C8	−1.2 (4)
C7—C11—C10—N3	0.5 (4)	C7—C8—C9—N3	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N3i	0.78 (3)	2.10 (3)	2.870 (3)	174.53

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯N3i	0.78 (3)	2.10 (3)	2.870 (3)	174.53

Symmetry code: (i) .