(E)-N'-(9-Anthryl-methyl-idene)-p-toluene-sulfono-hydrazide.

The S-N(H)-N=C linkage in the title mol-ecule, C(22)H(18)N(2)O(2)S, is non-planar [torsion angle = 30.6 (1)°] as the amino N atom is pyramidally coordinated. In the crystal, the amino group acts as a hydrogen-bond donor to an O atom of an adjacent mol-ecule, generating chains running parallel to the b axis.

Related literature

For the structure of the (E)-N′-benzyl­idene-p-toluene­sulf­ono­hydrazide analog, see: Mehrabi et al. (2008 ▶).

Experimental

Crystal data

C22H18N2O2S

M = 374.44

Orthorhombic,

a = 17.3634 (15) Å

b = 9.2438 (8) Å

c = 22.882 (2) Å

V = 3672.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.990

22220 measured reflections

4209 independent reflections

3158 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.02

4209 reflections

249 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003271X/pk2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003271X/pk2262Isup2.hkl

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

C22H18N2O2S	F(000) = 1568
Mr = 374.44	Dx = 1.354 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3593 reflections
a = 17.3634 (15) Å	θ = 2.3–27.6°
b = 9.2438 (8) Å	µ = 0.20 mm−1
c = 22.882 (2) Å	T = 100 K
V = 3672.6 (6) Å3	Prism, yellow
Z = 8	0.40 × 0.20 × 0.05 mm

Bruker SMART APEX diffractometer	4209 independent reflections
Radiation source: fine-focus sealed tube	3158 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→22
Tmin = 0.926, Tmax = 0.990	k = −12→10
22220 measured reflections	l = −29→29

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0442P)2 + 1.8913P] where P = (Fo2 + 2Fc2)/3
4209 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.70021 (2)	0.57688 (5)	0.781940 (19)	0.01816 (12)
O1	0.67930 (7)	0.71367 (13)	0.75666 (6)	0.0228 (3)
O2	0.75969 (7)	0.57170 (14)	0.82533 (5)	0.0244 (3)
N1	0.73235 (8)	0.47229 (17)	0.72874 (6)	0.0188 (3)
H1	0.7581 (11)	0.4002 (17)	0.7419 (9)	0.032 (6)*
N2	0.67630 (8)	0.44447 (16)	0.68590 (6)	0.0187 (3)
C1	0.61574 (10)	0.4956 (2)	0.80808 (8)	0.0207 (4)
C2	0.54464 (11)	0.5595 (2)	0.79729 (9)	0.0263 (4)
H2	0.5412	0.6474	0.7760	0.032*
C3	0.47881 (11)	0.4919 (2)	0.81839 (9)	0.0324 (5)
H3	0.4299	0.5341	0.8111	0.039*
C4	0.48310 (12)	0.3638 (2)	0.84988 (9)	0.0319 (5)
C5	0.55497 (13)	0.3014 (2)	0.85908 (9)	0.0326 (5)
H5	0.5584	0.2129	0.8800	0.039*
C6	0.62165 (11)	0.3659 (2)	0.83825 (8)	0.0256 (4)
H6	0.6705	0.3220	0.8445	0.031*
C7	0.41088 (13)	0.2933 (3)	0.87297 (10)	0.0437 (6)
H7A	0.3755	0.3679	0.8872	0.066*
H7B	0.4242	0.2279	0.9051	0.066*
H7C	0.3861	0.2382	0.8416	0.066*
C8	0.68260 (10)	0.32154 (19)	0.66045 (7)	0.0190 (4)
H8	0.7224	0.2580	0.6727	0.023*
C9	0.63107 (10)	0.27431 (19)	0.61321 (7)	0.0181 (4)
C10	0.55246 (10)	0.31693 (19)	0.61075 (8)	0.0196 (4)
C11	0.51458 (10)	0.3970 (2)	0.65569 (8)	0.0225 (4)
H11	0.5434	0.4292	0.6885	0.027*
C12	0.43788 (11)	0.4284 (2)	0.65260 (9)	0.0256 (4)
H12	0.4139	0.4789	0.6839	0.031*
C13	0.39353 (11)	0.3870 (2)	0.60350 (9)	0.0284 (4)
H13	0.3406	0.4124	0.6013	0.034*
C14	0.42673 (11)	0.3113 (2)	0.55987 (9)	0.0274 (4)
H14	0.3968	0.2849	0.5268	0.033*
C15	0.50621 (10)	0.2698 (2)	0.56239 (8)	0.0232 (4)
C16	0.53801 (11)	0.1800 (2)	0.51995 (8)	0.0248 (4)
H16	0.5071	0.1511	0.4877	0.030*
C17	0.61374 (10)	0.1311 (2)	0.52330 (8)	0.0207 (4)
C18	0.64417 (11)	0.0329 (2)	0.48093 (8)	0.0249 (4)
H18	0.6121	0.0005	0.4500	0.030*
C19	0.71804 (11)	−0.0149 (2)	0.48399 (8)	0.0247 (4)
H19	0.7372	−0.0808	0.4557	0.030*
C20	0.76612 (11)	0.0344 (2)	0.52973 (8)	0.0229 (4)
H20	0.8179	0.0017	0.5316	0.028*
C21	0.73965 (10)	0.1276 (2)	0.57109 (8)	0.0204 (4)
H21	0.7736	0.1594	0.6010	0.025*
C22	0.66168 (10)	0.17906 (19)	0.57053 (7)	0.0184 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0166 (2)	0.0169 (2)	0.0210 (2)	−0.00194 (17)	0.00059 (17)	−0.00158 (17)
O1	0.0222 (7)	0.0163 (6)	0.0300 (7)	−0.0008 (5)	0.0016 (5)	0.0003 (5)
O2	0.0203 (7)	0.0287 (7)	0.0241 (7)	−0.0025 (6)	−0.0044 (5)	−0.0040 (6)
N1	0.0164 (7)	0.0189 (8)	0.0211 (8)	0.0014 (6)	−0.0012 (6)	−0.0008 (6)
N2	0.0167 (7)	0.0209 (8)	0.0184 (7)	−0.0022 (6)	−0.0009 (6)	−0.0003 (6)
C1	0.0204 (9)	0.0205 (9)	0.0212 (9)	−0.0052 (7)	0.0050 (7)	−0.0043 (7)
C2	0.0219 (9)	0.0249 (10)	0.0323 (10)	−0.0008 (8)	0.0037 (8)	−0.0067 (8)
C3	0.0222 (10)	0.0366 (12)	0.0386 (12)	−0.0036 (9)	0.0077 (9)	−0.0149 (10)
C4	0.0330 (11)	0.0353 (12)	0.0274 (10)	−0.0164 (9)	0.0122 (9)	−0.0173 (9)
C5	0.0449 (13)	0.0250 (11)	0.0279 (10)	−0.0115 (9)	0.0087 (9)	−0.0030 (9)
C6	0.0296 (10)	0.0220 (10)	0.0252 (9)	−0.0029 (8)	0.0049 (8)	−0.0017 (8)
C7	0.0381 (13)	0.0554 (16)	0.0375 (12)	−0.0261 (11)	0.0144 (10)	−0.0162 (11)
C8	0.0177 (9)	0.0198 (9)	0.0195 (9)	0.0003 (7)	0.0016 (7)	0.0035 (7)
C9	0.0190 (9)	0.0171 (9)	0.0182 (8)	−0.0017 (7)	0.0004 (7)	0.0026 (7)
C10	0.0187 (9)	0.0184 (9)	0.0216 (9)	−0.0010 (7)	−0.0008 (7)	0.0031 (7)
C11	0.0197 (9)	0.0241 (10)	0.0238 (9)	−0.0020 (7)	0.0005 (7)	−0.0015 (8)
C12	0.0220 (9)	0.0249 (10)	0.0300 (10)	0.0017 (8)	0.0035 (8)	−0.0020 (8)
C13	0.0184 (9)	0.0299 (11)	0.0369 (11)	0.0042 (8)	−0.0030 (8)	0.0015 (9)
C14	0.0229 (10)	0.0311 (11)	0.0282 (10)	0.0044 (8)	−0.0083 (8)	−0.0004 (9)
C15	0.0213 (9)	0.0248 (10)	0.0235 (9)	0.0015 (8)	−0.0036 (7)	0.0035 (8)
C16	0.0243 (10)	0.0297 (10)	0.0203 (9)	0.0018 (8)	−0.0067 (8)	−0.0007 (8)
C17	0.0222 (9)	0.0218 (9)	0.0182 (8)	0.0009 (7)	−0.0005 (7)	0.0022 (7)
C18	0.0274 (10)	0.0283 (10)	0.0191 (9)	−0.0004 (8)	−0.0040 (8)	−0.0010 (8)
C19	0.0289 (10)	0.0252 (10)	0.0200 (9)	0.0015 (8)	0.0039 (8)	−0.0007 (8)
C20	0.0199 (9)	0.0231 (10)	0.0258 (10)	0.0020 (7)	0.0023 (7)	0.0031 (8)
C21	0.0193 (9)	0.0210 (9)	0.0210 (8)	−0.0010 (7)	0.0005 (7)	0.0019 (7)
C22	0.0199 (9)	0.0176 (9)	0.0176 (8)	−0.0018 (7)	0.0001 (7)	0.0046 (7)

S1—O1	1.4370 (13)	C9—C10	1.422 (2)
S1—O2	1.4334 (13)	C10—C11	1.428 (2)
S1—N1	1.6516 (15)	C10—C15	1.435 (2)
S1—C1	1.7532 (18)	C11—C12	1.365 (3)
N1—N2	1.405 (2)	C11—H11	0.9500
N1—H1	0.857 (9)	C12—C13	1.415 (3)
N2—C8	1.281 (2)	C12—H12	0.9500
C1—C6	1.387 (3)	C13—C14	1.349 (3)
C1—C2	1.391 (3)	C13—H13	0.9500
C2—C3	1.389 (3)	C14—C15	1.434 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.388 (3)	C15—C16	1.392 (3)
C3—H3	0.9500	C16—C17	1.392 (3)
C4—C5	1.391 (3)	C16—H16	0.9500
C4—C7	1.509 (3)	C17—C18	1.429 (3)
C5—C6	1.387 (3)	C17—C22	1.434 (2)
C5—H5	0.9500	C18—C19	1.358 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.414 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—C21	1.360 (2)
C8—C9	1.470 (2)	C20—H20	0.9500
C8—H8	0.9500	C21—C22	1.435 (2)
C9—C22	1.418 (2)	C21—H21	0.9500
O1—S1—O2	119.35 (8)	C9—C10—C11	123.88 (16)
O1—S1—N1	107.68 (8)	C9—C10—C15	118.93 (16)
O2—S1—N1	104.33 (8)	C11—C10—C15	117.07 (16)
O1—S1—C1	107.65 (8)	C12—C11—C10	121.50 (18)
O2—S1—C1	110.62 (8)	C12—C11—H11	119.3
N1—S1—C1	106.45 (8)	C10—C11—H11	119.3
N2—N1—S1	112.79 (11)	C11—C12—C13	120.98 (18)
N2—N1—H1	117.7 (15)	C11—C12—H12	119.5
S1—N1—H1	111.8 (14)	C13—C12—H12	119.5
C8—N2—N1	114.84 (15)	C14—C13—C12	119.71 (17)
C6—C1—C2	121.41 (17)	C14—C13—H13	120.1
C6—C1—S1	118.58 (14)	C12—C13—H13	120.1
C2—C1—S1	120.00 (15)	C13—C14—C15	121.36 (18)
C3—C2—C1	118.52 (19)	C13—C14—H14	119.3
C3—C2—H2	120.7	C15—C14—H14	119.3
C1—C2—H2	120.7	C16—C15—C10	119.80 (16)
C4—C3—C2	121.3 (2)	C16—C15—C14	120.89 (17)
C4—C3—H3	119.3	C10—C15—C14	119.26 (17)
C2—C3—H3	119.3	C17—C16—C15	122.00 (17)
C3—C4—C5	118.72 (18)	C17—C16—H16	119.0
C3—C4—C7	120.4 (2)	C15—C16—H16	119.0
C5—C4—C7	120.9 (2)	C16—C17—C18	121.19 (17)
C6—C5—C4	121.3 (2)	C16—C17—C22	119.28 (17)
C6—C5—H5	119.4	C18—C17—C22	119.52 (16)
C4—C5—H5	119.4	C19—C18—C17	121.39 (17)
C5—C6—C1	118.73 (19)	C19—C18—H18	119.3
C5—C6—H6	120.6	C17—C18—H18	119.3
C1—C6—H6	120.6	C18—C19—C20	119.38 (17)
C4—C7—H7A	109.5	C18—C19—H19	120.3
C4—C7—H7B	109.5	C20—C19—H19	120.3
H7A—C7—H7B	109.5	C21—C20—C19	121.31 (17)
C4—C7—H7C	109.5	C21—C20—H20	119.3
H7A—C7—H7C	109.5	C19—C20—H20	119.3
H7B—C7—H7C	109.5	C20—C21—C22	121.52 (17)
N2—C8—C9	123.06 (16)	C20—C21—H21	119.2
N2—C8—H8	118.5	C22—C21—H21	119.2
C9—C8—H8	118.5	C9—C22—C21	123.60 (16)
C22—C9—C10	120.31 (16)	C9—C22—C17	119.55 (16)
C22—C9—C8	117.56 (15)	C21—C22—C17	116.85 (16)
C10—C9—C8	122.09 (16)
O1—S1—N1—N2	−62.00 (13)	C10—C11—C12—C13	−2.3 (3)
O2—S1—N1—N2	170.23 (11)	C11—C12—C13—C14	2.1 (3)
C1—S1—N1—N2	53.21 (14)	C12—C13—C14—C15	0.9 (3)
S1—N1—N2—C8	−149.39 (13)	C9—C10—C15—C16	2.1 (3)
O1—S1—C1—C6	−175.60 (14)	C11—C10—C15—C16	−174.03 (17)
O2—S1—C1—C6	−43.59 (17)	C9—C10—C15—C14	179.46 (17)
N1—S1—C1—C6	69.17 (16)	C11—C10—C15—C14	3.4 (3)
O1—S1—C1—C2	5.81 (18)	C13—C14—C15—C16	173.73 (19)
O2—S1—C1—C2	137.82 (15)	C13—C14—C15—C10	−3.6 (3)
N1—S1—C1—C2	−109.42 (16)	C10—C15—C16—C17	1.3 (3)
C6—C1—C2—C3	1.2 (3)	C14—C15—C16—C17	−176.08 (18)
S1—C1—C2—C3	179.71 (15)	C15—C16—C17—C18	176.73 (18)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C22	−2.6 (3)
C2—C3—C4—C5	−1.4 (3)	C16—C17—C18—C19	179.93 (18)
C2—C3—C4—C7	179.28 (18)	C22—C17—C18—C19	−0.8 (3)
C3—C4—C5—C6	1.0 (3)	C17—C18—C19—C20	−0.6 (3)
C7—C4—C5—C6	−179.68 (18)	C18—C19—C20—C21	0.7 (3)
C4—C5—C6—C1	0.4 (3)	C19—C20—C21—C22	0.6 (3)
C2—C1—C6—C5	−1.6 (3)	C10—C9—C22—C21	−177.99 (16)
S1—C1—C6—C5	179.88 (14)	C8—C9—C22—C21	−0.2 (3)
N1—N2—C8—C9	−178.04 (15)	C10—C9—C22—C17	2.8 (3)
N2—C8—C9—C22	149.92 (17)	C8—C9—C22—C17	−179.43 (15)
N2—C8—C9—C10	−32.4 (3)	C20—C21—C22—C9	178.91 (17)
C22—C9—C10—C11	171.73 (17)	C20—C21—C22—C17	−1.9 (3)
C8—C9—C10—C11	−5.9 (3)	C16—C17—C22—C9	0.5 (3)
C22—C9—C10—C15	−4.1 (3)	C18—C17—C22—C9	−178.81 (17)
C8—C9—C10—C15	178.27 (16)	C16—C17—C22—C21	−178.75 (17)
C9—C10—C11—C12	−176.38 (18)	C18—C17—C22—C21	1.9 (2)
C15—C10—C11—C12	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (1)	2.07 (1)	2.911 (2)	169 (2)

Symmetry code: (i) .