N'-(4-Bromo-benzyl-idene)quinoline-8-sulfonohydrazide.

In the title compound, C(16)H(12)BrN(3)O(2)S, the dihedral angle between the planes of the almost planar (r.m.s. deviation = 0.0263 Å) quinoline group and the bromo-phenyl group is 87.4 (1)°. The torsion angle of the central S-N-N-C bridge is 144.8 (2)°. The amino group has an intra-molecular contact to the quinoline N atom. The structure is stabilized by one N-H⋯O and two C-H⋯O inter-molecular hydrogen bonds.

Related literature

For general background, see: Dueñas-Romero et al. (2006 ▶); da Silva et al. (2007 ▶). For related compounds, see: Oliveira & Nunes (2006 ▶); Silva et al. (2006 ▶).

Experimental

Crystal data

C16H12BrN3O2S

M = 390.26

Monoclinic,

a = 32.149 (3) Å

b = 7.011 (1) Å

c = 16.589 (2) Å

β = 117.86 (1)°

V = 3305.7 (7) Å3

Z = 8

Cu Kα radiation

μ = 4.68 mm−1

T = 299 K

0.65 × 0.28 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.147, T max = 0.626

3889 measured reflections

2942 independent reflections

2677 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.05

2942 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −1.00 e Å−3

Data collection: CAD-4-PC (Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008848/im2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008848/im2087Isup2.hkl

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

C16H12BrN3O2S	F(000) = 1568
Mr = 390.26	Dx = 1.568 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 32.149 (3) Å	θ = 3.1–20.6°
b = 7.011 (1) Å	µ = 4.68 mm−1
c = 16.589 (2) Å	T = 299 K
β = 117.86 (1)°	Long plate, colorless
V = 3305.7 (7) Å3	0.65 × 0.28 × 0.10 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 66.9°, θmin = 3.1°
ω/2θ scans	h = −36→38
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
Tmin = 0.147, Tmax = 0.626	l = −19→4
3889 measured reflections	3 standard reflections every 120 min
2942 independent reflections	intensity decay: 1.5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0805P)2 + 6.9219P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.007
2942 reflections	Δρmax = 0.75 e Å−3
212 parameters	Δρmin = −1.00 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00043 (7)

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.

	x	y	z	Uiso*/Ueq
Br1	−0.070685 (17)	−0.11247 (10)	0.09298 (5)	0.0984 (3)
S1	0.19475 (2)	0.54754 (10)	0.16299 (5)	0.0399 (2)
O1	0.24468 (8)	0.5560 (3)	0.20074 (15)	0.0506 (6)
O2	0.16963 (9)	0.7062 (3)	0.17320 (17)	0.0550 (6)
N1	0.18486 (8)	0.3613 (4)	0.21089 (16)	0.0383 (5)
H1N	0.2045 (13)	0.269 (6)	0.214 (2)	0.046*
N2	0.13725 (8)	0.3233 (4)	0.18004 (16)	0.0401 (5)
N3	0.20861 (9)	0.1911 (4)	0.07924 (17)	0.0454 (6)
C1	0.17125 (10)	0.4981 (4)	0.04547 (19)	0.0406 (6)
C2	0.14454 (13)	0.6347 (5)	−0.0160 (2)	0.0535 (8)
H2	0.1358	0.7442	0.0039	0.064*
C3	0.13046 (15)	0.6088 (6)	−0.1090 (3)	0.0670 (11)
H3	0.1119	0.7007	−0.1508	0.080*
C4	0.14362 (15)	0.4515 (6)	−0.1386 (2)	0.0646 (11)
H4	0.1348	0.4384	−0.2003	0.077*
C5	0.17042 (12)	0.3077 (5)	−0.0775 (2)	0.0501 (8)
C6	0.18600 (15)	0.1403 (6)	−0.1035 (3)	0.0624 (10)
H6	0.1789	0.1220	−0.1641	0.075*
C7	0.21095 (14)	0.0087 (6)	−0.0407 (3)	0.0638 (10)
H7	0.2216	−0.1004	−0.0573	0.077*
C8	0.22084 (13)	0.0368 (5)	0.0498 (3)	0.0552 (8)
H8	0.2370	−0.0587	0.0918	0.066*
C9	0.18388 (10)	0.3272 (4)	0.01633 (19)	0.0405 (6)
C10	0.12657 (11)	0.1475 (5)	0.1748 (2)	0.0424 (7)
H10	0.1494	0.0554	0.1854	0.051*
C11	0.07855 (12)	0.0890 (5)	0.1521 (2)	0.0467 (7)
C12	0.06707 (15)	−0.1023 (6)	0.1405 (3)	0.0679 (11)
H12	0.0894	−0.1918	0.1449	0.082*
C13	0.02227 (16)	−0.1614 (7)	0.1221 (4)	0.0785 (12)
H13	0.0145	−0.2903	0.1142	0.094*
C14	−0.01013 (13)	−0.0307 (6)	0.1158 (3)	0.0639 (10)
C15	0.00053 (14)	0.1602 (7)	0.1269 (3)	0.0758 (12)
H15	−0.0220	0.2487	0.1224	0.091*
C16	0.04473 (13)	0.2196 (6)	0.1446 (3)	0.0657 (10)
H16	0.0519	0.3489	0.1516	0.079*

	U11	U22	U33	U12	U13	U23
Br1	0.0546 (3)	0.1028 (5)	0.1379 (6)	−0.0215 (3)	0.0451 (3)	0.0083 (3)
S1	0.0378 (4)	0.0351 (4)	0.0470 (4)	−0.0033 (3)	0.0202 (3)	−0.0071 (3)
O1	0.0393 (12)	0.0493 (13)	0.0586 (12)	−0.0131 (10)	0.0189 (10)	−0.0155 (10)
O2	0.0625 (14)	0.0372 (11)	0.0706 (14)	0.0061 (11)	0.0356 (12)	−0.0071 (10)
N1	0.0326 (12)	0.0390 (13)	0.0421 (12)	0.0041 (10)	0.0164 (10)	0.0014 (10)
N2	0.0346 (12)	0.0430 (14)	0.0435 (12)	0.0001 (11)	0.0189 (10)	−0.0027 (10)
N3	0.0453 (14)	0.0429 (14)	0.0519 (14)	−0.0017 (12)	0.0259 (12)	−0.0043 (11)
C1	0.0401 (15)	0.0382 (15)	0.0444 (15)	−0.0080 (12)	0.0206 (12)	−0.0009 (12)
C2	0.0531 (19)	0.0418 (17)	0.0601 (19)	−0.0021 (15)	0.0219 (16)	0.0094 (14)
C3	0.070 (3)	0.063 (2)	0.056 (2)	−0.0072 (19)	0.0195 (18)	0.0198 (18)
C4	0.071 (2)	0.077 (3)	0.0429 (17)	−0.024 (2)	0.0244 (17)	0.0044 (17)
C5	0.0496 (17)	0.061 (2)	0.0467 (16)	−0.0209 (16)	0.0282 (14)	−0.0089 (15)
C6	0.071 (2)	0.070 (2)	0.061 (2)	−0.027 (2)	0.0441 (19)	−0.0252 (19)
C7	0.065 (2)	0.060 (2)	0.082 (3)	−0.0125 (19)	0.047 (2)	−0.026 (2)
C8	0.0527 (19)	0.0480 (19)	0.074 (2)	−0.0014 (15)	0.0368 (17)	−0.0094 (16)
C9	0.0375 (14)	0.0438 (16)	0.0446 (15)	−0.0112 (13)	0.0227 (12)	−0.0029 (12)
C10	0.0392 (15)	0.0413 (16)	0.0469 (15)	0.0020 (13)	0.0203 (13)	0.0002 (12)
C11	0.0424 (16)	0.0472 (17)	0.0517 (16)	−0.0041 (14)	0.0231 (14)	0.0008 (13)
C12	0.055 (2)	0.048 (2)	0.104 (3)	−0.0022 (16)	0.039 (2)	0.0016 (19)
C13	0.062 (2)	0.053 (2)	0.121 (4)	−0.014 (2)	0.043 (2)	−0.002 (2)
C14	0.0454 (19)	0.070 (3)	0.075 (2)	−0.0129 (18)	0.0271 (17)	0.0046 (19)
C15	0.048 (2)	0.068 (3)	0.112 (3)	0.0004 (19)	0.038 (2)	−0.003 (2)
C16	0.0480 (19)	0.049 (2)	0.098 (3)	−0.0031 (17)	0.0332 (19)	−0.004 (2)

Br1—C14	1.890 (4)	C5—C6	1.420 (5)
S1—O1	1.426 (2)	C6—C7	1.342 (6)
S1—O2	1.431 (2)	C6—H6	0.9300
S1—N1	1.635 (3)	C7—C8	1.395 (5)
S1—C1	1.765 (3)	C7—H7	0.9300
N1—N2	1.394 (3)	C8—H8	0.9300
N1—H1N	0.89 (4)	C10—C11	1.467 (4)
N2—C10	1.271 (4)	C10—H10	0.9300
N3—C8	1.320 (4)	C11—C12	1.380 (5)
N3—C9	1.362 (4)	C11—C16	1.382 (5)
C1—C2	1.369 (5)	C12—C13	1.389 (6)
C1—C9	1.421 (4)	C12—H12	0.9300
C2—C3	1.403 (5)	C13—C14	1.354 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.353 (6)	C14—C15	1.373 (6)
C3—H3	0.9300	C15—C16	1.374 (5)
C4—C5	1.403 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C9	1.413 (4)
O1—S1—O2	119.85 (14)	C6—C7—H7	120.3
O1—S1—N1	104.74 (14)	C8—C7—H7	120.3
O2—S1—N1	108.35 (14)	N3—C8—C7	123.7 (4)
O1—S1—C1	107.83 (14)	N3—C8—H8	118.1
O2—S1—C1	108.02 (15)	C7—C8—H8	118.1
N1—S1—C1	107.45 (13)	N3—C9—C5	123.0 (3)
N2—N1—S1	113.80 (19)	N3—C9—C1	119.2 (3)
N2—N1—H1N	121 (2)	C5—C9—C1	117.8 (3)
S1—N1—H1N	108 (2)	N2—C10—C11	120.5 (3)
C10—N2—N1	115.2 (3)	N2—C10—H10	119.8
C8—N3—C9	117.3 (3)	C11—C10—H10	119.8
C2—C1—C9	121.1 (3)	C12—C11—C16	118.9 (3)
C2—C1—S1	118.7 (3)	C12—C11—C10	119.2 (3)
C9—C1—S1	119.9 (2)	C16—C11—C10	121.8 (3)
C1—C2—C3	119.7 (4)	C11—C12—C13	120.2 (4)
C1—C2—H2	120.1	C11—C12—H12	119.9
C3—C2—H2	120.1	C13—C12—H12	119.9
C4—C3—C2	120.6 (4)	C14—C13—C12	119.8 (4)
C4—C3—H3	119.7	C14—C13—H13	120.1
C2—C3—H3	119.7	C12—C13—H13	120.1
C3—C4—C5	121.0 (3)	C13—C14—C15	121.0 (4)
C3—C4—H4	119.5	C13—C14—Br1	119.6 (3)
C5—C4—H4	119.5	C15—C14—Br1	119.5 (3)
C4—C5—C9	119.6 (3)	C14—C15—C16	119.5 (4)
C4—C5—C6	124.0 (3)	C14—C15—H15	120.2
C9—C5—C6	116.4 (3)	C16—C15—H15	120.2
C7—C6—C5	120.0 (3)	C15—C16—C11	120.7 (4)
C7—C6—H6	120.0	C15—C16—H16	119.7
C5—C6—H6	120.0	C11—C16—H16	119.7
C6—C7—C8	119.5 (3)
O1—S1—N1—N2	−177.68 (19)	C8—N3—C9—C1	−178.1 (3)
O2—S1—N1—N2	53.3 (2)	C4—C5—C9—N3	177.9 (3)
C1—S1—N1—N2	−63.2 (2)	C6—C5—C9—N3	−2.9 (4)
S1—N1—N2—C10	144.8 (2)	C4—C5—C9—C1	−2.8 (4)
O1—S1—C1—C2	−113.8 (3)	C6—C5—C9—C1	176.4 (3)
O2—S1—C1—C2	17.1 (3)	C2—C1—C9—N3	−176.9 (3)
N1—S1—C1—C2	133.8 (3)	S1—C1—C9—N3	9.3 (4)
O1—S1—C1—C9	60.2 (3)	C2—C1—C9—C5	3.7 (4)
O2—S1—C1—C9	−168.9 (2)	S1—C1—C9—C5	−170.1 (2)
N1—S1—C1—C9	−52.2 (3)	N1—N2—C10—C11	173.8 (2)
C9—C1—C2—C3	−1.9 (5)	N2—C10—C11—C12	175.4 (3)
S1—C1—C2—C3	172.0 (3)	N2—C10—C11—C16	−6.5 (5)
C1—C2—C3—C4	−1.0 (6)	C16—C11—C12—C13	−0.4 (7)
C2—C3—C4—C5	2.0 (6)	C10—C11—C12—C13	177.7 (4)
C3—C4—C5—C9	0.0 (5)	C11—C12—C13—C14	−0.1 (7)
C3—C4—C5—C6	−179.1 (4)	C12—C13—C14—C15	0.3 (7)
C4—C5—C6—C7	−179.1 (3)	C12—C13—C14—Br1	−178.9 (4)
C9—C5—C6—C7	1.8 (5)	C13—C14—C15—C16	0.0 (7)
C5—C6—C7—C8	0.8 (6)	Br1—C14—C15—C16	179.2 (3)
C9—N3—C8—C7	1.8 (5)	C14—C15—C16—C11	−0.5 (7)
C6—C7—C8—N3	−2.8 (6)	C12—C11—C16—C15	0.8 (6)
C8—N3—C9—C5	1.2 (4)	C10—C11—C16—C15	−177.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1—H1N···N3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10—H10···O2ii	0.93	2.57	3.395 (4)	149
C12—H12···O2ii	0.93	2.50	3.361 (5)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.89 (4)	2.18 (4)	2.959 (3)	146 (3)
N1—H1N⋯N3	0.89 (4)	2.36 (3)	2.887 (4)	118 (3)
C10—H10⋯O2ii	0.93	2.57	3.395 (4)	149
C12—H12⋯O2ii	0.93	2.50	3.361 (5)	154

Symmetry codes: (i) ; (ii) .