(E)-4-[(4-Nitro­phen­yl)hydrazonometh­yl]phenyl p-toluene­sulfonate

In the title compound, C₂₀H₁₇N₃O₅S, the central benzene ring makes dihedral angles of 56.33 (7) and 1.76 (8)° with the terminal 4-methyl­benzene ring and the mean plane of the nitro­phenyl­hydrazine residue, respectively. The crystal packing is stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.043
• wR factor = 0.119
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-4-[(4-Nitrophenyl)hydrazonomethyl]phenyl p-toluenesulfonate

Crystal data

C20H17N3O5S	F(000) = 856
Mr = 411.44	Dx = 1.409 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3297 reflections
a = 8.0073 (19) Å	θ = 2.7–25.5°
b = 12.440 (3) Å	µ = 0.21 mm^−1
c = 19.855 (5) Å	T = 294 K
β = 101.206 (4)°	Block, yellow
V = 1940.1 (8) Å^3	0.50 × 0.30 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3965 independent reflections
Radiation source: fine-focus sealed tube	2598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→5
Tmin = 0.891, Tmax = 0.956	k = −15→14
10636 measured reflections	l = −19→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.2437P] where P = (Fo^2 + 2Fc^2)/3
3965 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.46613 (7)	0.16762 (4)	0.20498 (3)	0.04397 (17)
O1	0.56553 (18)	0.16607 (12)	0.15296 (8)	0.0557 (4)
O2	0.43604 (19)	0.07046 (11)	0.23764 (8)	0.0580 (4)
O3	0.56799 (16)	0.24904 (11)	0.25967 (7)	0.0465 (4)
O4	−0.0425 (3)	0.92549 (15)	0.66762 (11)	0.0893 (7)
O5	−0.0768 (3)	0.96522 (14)	0.56153 (11)	0.0829 (6)
N1	0.26070 (19)	0.47462 (13)	0.49785 (8)	0.0394 (4)
N2	0.2009 (2)	0.49722 (13)	0.55585 (9)	0.0431 (4)
H2	0.1991	0.4475	0.5858	0.052*
N3	−0.0353 (2)	0.90279 (15)	0.60885 (12)	0.0562 (5)
C1	0.2733 (2)	0.23325 (15)	0.17587 (10)	0.0388 (5)
C2	0.2708 (3)	0.32565 (18)	0.13722 (12)	0.0508 (6)
H2A	0.3700	0.3508	0.1249	0.061*
C3	0.1202 (3)	0.37986 (19)	0.11721 (13)	0.0597 (6)
H3	0.1179	0.4423	0.0913	0.072*
C4	−0.0291 (3)	0.34279 (19)	0.13512 (13)	0.0544 (6)
C5	−0.0232 (3)	0.2503 (2)	0.17299 (12)	0.0543 (6)
H5	−0.1226	0.2243	0.1848	0.065*
C6	0.1270 (3)	0.19483 (18)	0.19395 (11)	0.0471 (5)
H6	0.1294	0.1324	0.2199	0.057*
C7	−0.1938 (3)	0.4045 (2)	0.11448 (18)	0.0884 (10)
H7A	−0.2881	0.3556	0.1098	0.133*
H7B	−0.1951	0.4400	0.0715	0.133*
H7C	−0.2027	0.4569	0.1491	0.133*
C8	0.4964 (2)	0.27825 (16)	0.31712 (11)	0.0394 (5)
C9	0.4944 (3)	0.20772 (18)	0.36954 (12)	0.0509 (6)
H9	0.5330	0.1376	0.3670	0.061*
C10	0.4342 (3)	0.24214 (17)	0.42615 (11)	0.0503 (6)
H10	0.4321	0.1943	0.4620	0.060*
C11	0.3770 (2)	0.34576 (15)	0.43116 (10)	0.0384 (5)
C12	0.3809 (3)	0.41549 (17)	0.37683 (11)	0.0473 (5)
H12	0.3427	0.4858	0.3790	0.057*
C13	0.4404 (3)	0.38200 (17)	0.32005 (12)	0.0489 (5)
H13	0.4427	0.4292	0.2839	0.059*
C14	0.3134 (2)	0.37927 (17)	0.49154 (10)	0.0419 (5)
H14	0.3110	0.3298	0.5265	0.050*
C15	0.1436 (2)	0.59797 (15)	0.56727 (10)	0.0363 (5)
C16	0.0922 (2)	0.61762 (17)	0.62924 (11)	0.0427 (5)
H16	0.0965	0.5627	0.6613	0.051*
C17	0.0354 (3)	0.71745 (17)	0.64314 (11)	0.0451 (5)
H17	0.0030	0.7311	0.6848	0.054*
C18	0.0268 (2)	0.79751 (16)	0.59460 (11)	0.0426 (5)
C19	0.0759 (3)	0.77915 (17)	0.53259 (11)	0.0454 (5)
H19	0.0682	0.8338	0.5001	0.055*
C20	0.1359 (2)	0.67992 (16)	0.51933 (11)	0.0421 (5)
H20	0.1716	0.6674	0.4782	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0438 (3)	0.0413 (3)	0.0485 (4)	−0.0023 (2)	0.0132 (2)	−0.0130 (2)
O1	0.0509 (9)	0.0622 (10)	0.0590 (11)	0.0005 (7)	0.0229 (8)	−0.0197 (8)
O2	0.0691 (10)	0.0387 (9)	0.0652 (11)	−0.0017 (7)	0.0105 (8)	−0.0037 (7)
O3	0.0381 (8)	0.0527 (9)	0.0503 (9)	−0.0060 (6)	0.0126 (6)	−0.0174 (7)
O4	0.1483 (19)	0.0595 (12)	0.0737 (15)	0.0149 (11)	0.0552 (13)	−0.0105 (10)
O5	0.1221 (16)	0.0525 (11)	0.0826 (14)	0.0274 (10)	0.0412 (12)	0.0121 (10)
N1	0.0402 (9)	0.0408 (10)	0.0380 (10)	−0.0030 (7)	0.0097 (7)	−0.0042 (7)
N2	0.0561 (10)	0.0389 (10)	0.0367 (10)	−0.0007 (8)	0.0153 (8)	0.0009 (8)
N3	0.0671 (13)	0.0444 (11)	0.0645 (15)	0.0002 (9)	0.0314 (11)	−0.0032 (11)
C1	0.0376 (10)	0.0396 (11)	0.0416 (12)	−0.0065 (8)	0.0136 (9)	−0.0103 (9)
C2	0.0461 (12)	0.0505 (13)	0.0594 (15)	−0.0087 (10)	0.0187 (11)	−0.0009 (11)
C3	0.0602 (15)	0.0498 (14)	0.0676 (17)	−0.0025 (11)	0.0086 (12)	0.0049 (12)
C4	0.0429 (12)	0.0564 (14)	0.0603 (16)	−0.0011 (10)	0.0009 (11)	−0.0166 (12)
C5	0.0382 (12)	0.0658 (16)	0.0599 (16)	−0.0145 (10)	0.0123 (10)	−0.0139 (12)
C6	0.0465 (12)	0.0501 (13)	0.0468 (13)	−0.0131 (10)	0.0143 (10)	−0.0048 (10)
C7	0.0526 (15)	0.0773 (19)	0.126 (3)	0.0069 (14)	−0.0056 (16)	−0.0112 (18)
C8	0.0328 (10)	0.0442 (12)	0.0408 (12)	−0.0031 (8)	0.0065 (8)	−0.0120 (10)
C9	0.0584 (14)	0.0390 (12)	0.0543 (15)	0.0143 (10)	0.0081 (11)	−0.0027 (11)
C10	0.0635 (14)	0.0430 (12)	0.0437 (14)	0.0108 (10)	0.0085 (11)	0.0044 (10)
C11	0.0356 (10)	0.0383 (11)	0.0396 (12)	−0.0003 (8)	0.0029 (8)	−0.0030 (9)
C12	0.0603 (13)	0.0342 (11)	0.0505 (14)	0.0041 (9)	0.0185 (11)	−0.0036 (10)
C13	0.0625 (14)	0.0380 (12)	0.0488 (14)	−0.0005 (10)	0.0167 (11)	0.0007 (10)
C14	0.0448 (11)	0.0410 (12)	0.0392 (13)	−0.0005 (9)	0.0062 (9)	0.0015 (9)
C15	0.0326 (10)	0.0379 (11)	0.0384 (12)	−0.0047 (8)	0.0067 (8)	−0.0044 (9)
C16	0.0492 (12)	0.0427 (12)	0.0381 (12)	−0.0052 (9)	0.0129 (9)	0.0008 (9)
C17	0.0500 (12)	0.0487 (13)	0.0403 (13)	−0.0048 (10)	0.0181 (10)	−0.0056 (10)
C18	0.0428 (11)	0.0385 (11)	0.0487 (13)	−0.0030 (9)	0.0140 (9)	−0.0052 (10)
C19	0.0534 (13)	0.0428 (12)	0.0425 (13)	0.0002 (10)	0.0152 (10)	0.0072 (10)
C20	0.0476 (12)	0.0453 (12)	0.0360 (12)	−0.0019 (9)	0.0146 (9)	0.0002 (9)

Geometric parameters (Å, º)

S1—O2	1.4143 (16)	C7—H7B	0.9600
S1—O1	1.4213 (15)	C7—H7C	0.9600
S1—O3	1.5893 (14)	C8—C9	1.364 (3)
S1—C1	1.743 (2)	C8—C13	1.371 (3)
O3—C8	1.420 (2)	C9—C10	1.375 (3)
O4—N3	1.213 (2)	C9—H9	0.9300
O5—N3	1.214 (3)	C10—C11	1.378 (3)
N1—C14	1.273 (2)	C10—H10	0.9300
N1—N2	1.360 (2)	C11—C12	1.389 (3)
N2—C15	1.369 (2)	C11—C14	1.452 (3)
N2—H2	0.8600	C12—C13	1.371 (3)
N3—C18	1.448 (3)	C12—H12	0.9300
C1—C6	1.375 (3)	C13—H13	0.9300
C1—C2	1.380 (3)	C14—H14	0.9300
C2—C3	1.371 (3)	C15—C20	1.388 (3)
C2—H2A	0.9300	C15—C16	1.393 (3)
C3—C4	1.390 (3)	C16—C17	1.369 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.371 (3)	C17—C18	1.378 (3)
C4—C7	1.512 (3)	C17—H17	0.9300
C5—C6	1.378 (3)	C18—C19	1.382 (3)
C5—H5	0.9300	C19—C20	1.369 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—H7A	0.9600	C20—H20	0.9300
O2—S1—O1	119.40 (9)	C9—C8—O3	121.00 (18)
O2—S1—O3	109.99 (9)	C13—C8—O3	117.49 (19)
O1—S1—O3	102.69 (8)	C8—C9—C10	118.8 (2)
O2—S1—C1	109.48 (9)	C8—C9—H9	120.6
O1—S1—C1	110.52 (10)	C10—C9—H9	120.6
O3—S1—C1	103.42 (8)	C9—C10—C11	121.6 (2)
C8—O3—S1	118.58 (11)	C9—C10—H10	119.2
C14—N1—N2	116.99 (17)	C11—C10—H10	119.2
N1—N2—C15	120.95 (16)	C10—C11—C12	118.0 (2)
N1—N2—H2	119.5	C10—C11—C14	120.20 (19)
C15—N2—H2	119.5	C12—C11—C14	121.75 (18)
O4—N3—O5	122.6 (2)	C13—C12—C11	120.8 (2)
O4—N3—C18	118.7 (2)	C13—C12—H12	119.6
O5—N3—C18	118.7 (2)	C11—C12—H12	119.6
C6—C1—C2	120.89 (19)	C12—C13—C8	119.3 (2)
C6—C1—S1	119.68 (17)	C12—C13—H13	120.3
C2—C1—S1	119.38 (15)	C8—C13—H13	120.3
C3—C2—C1	119.2 (2)	N1—C14—C11	121.66 (19)
C3—C2—H2A	120.4	N1—C14—H14	119.2
C1—C2—H2A	120.4	C11—C14—H14	119.2
C2—C3—C4	120.9 (2)	N2—C15—C20	122.05 (18)
C2—C3—H3	119.5	N2—C15—C16	118.24 (18)
C4—C3—H3	119.5	C20—C15—C16	119.71 (19)
C5—C4—C3	118.6 (2)	C17—C16—C15	120.27 (19)
C5—C4—C7	120.7 (2)	C17—C16—H16	119.9
C3—C4—C7	120.7 (2)	C15—C16—H16	119.9
C4—C5—C6	121.4 (2)	C16—C17—C18	119.20 (19)
C4—C5—H5	119.3	C16—C17—H17	120.4
C6—C5—H5	119.3	C18—C17—H17	120.4
C1—C6—C5	119.0 (2)	C17—C18—C19	121.29 (19)
C1—C6—H6	120.5	C17—C18—N3	119.28 (19)
C5—C6—H6	120.5	C19—C18—N3	119.43 (19)
C4—C7—H7A	109.5	C20—C19—C18	119.45 (19)
C4—C7—H7B	109.5	C20—C19—H19	120.3
H7A—C7—H7B	109.5	C18—C19—H19	120.3
C4—C7—H7C	109.5	C19—C20—C15	120.07 (19)
H7A—C7—H7C	109.5	C19—C20—H20	120.0
H7B—C7—H7C	109.5	C15—C20—H20	120.0
C9—C8—C13	121.4 (2)
O2—S1—O3—C8	−57.41 (16)	C9—C10—C11—C14	179.63 (19)
O1—S1—O3—C8	174.46 (14)	C10—C11—C12—C13	−0.1 (3)
C1—S1—O3—C8	59.43 (16)	C14—C11—C12—C13	−179.50 (18)
C14—N1—N2—C15	179.23 (17)	C11—C12—C13—C8	0.0 (3)
O2—S1—C1—C6	8.0 (2)	C9—C8—C13—C12	−0.1 (3)
O1—S1—C1—C6	141.49 (16)	O3—C8—C13—C12	−175.68 (17)
O3—S1—C1—C6	−109.22 (17)	N2—N1—C14—C11	178.89 (16)
O2—S1—C1—C2	−174.59 (17)	C10—C11—C14—N1	179.53 (19)
O1—S1—C1—C2	−41.08 (19)	C12—C11—C14—N1	−1.1 (3)
O3—S1—C1—C2	68.21 (19)	N1—N2—C15—C20	3.2 (3)
C6—C1—C2—C3	0.5 (3)	N1—N2—C15—C16	−176.71 (16)
S1—C1—C2—C3	−176.90 (17)	N2—C15—C16—C17	179.41 (18)
C1—C2—C3—C4	−0.2 (4)	C20—C15—C16—C17	−0.5 (3)
C2—C3—C4—C5	−0.4 (4)	C15—C16—C17—C18	1.2 (3)
C2—C3—C4—C7	178.4 (2)	C16—C17—C18—C19	−0.6 (3)
C3—C4—C5—C6	0.7 (3)	C16—C17—C18—N3	179.21 (19)
C7—C4—C5—C6	−178.1 (2)	O4—N3—C18—C17	16.1 (3)
C2—C1—C6—C5	−0.2 (3)	O5—N3—C18—C17	−164.5 (2)
S1—C1—C6—C5	177.23 (16)	O4—N3—C18—C19	−164.0 (2)
C4—C5—C6—C1	−0.5 (3)	O5—N3—C18—C19	15.4 (3)
S1—O3—C8—C9	73.4 (2)	C17—C18—C19—C20	−0.7 (3)
S1—O3—C8—C13	−111.00 (18)	N3—C18—C19—C20	179.47 (18)
C13—C8—C9—C10	0.2 (3)	C18—C19—C20—C15	1.4 (3)
O3—C8—C9—C10	175.63 (18)	N2—C15—C20—C19	179.26 (18)
C8—C9—C10—C11	−0.3 (3)	C16—C15—C20—C19	−0.9 (3)
C9—C10—C11—C12	0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.93	2.56	3.405 (3)	151
N2—H2···O1^ii	0.86	2.34	3.136 (2)	154

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