4-Methyl-N′-[(E)-4-methyl­benzyl­idene]benzene­sulfonohydrazide

Reaction of toluene-4-sulfonohydrazide with 4-methyl­benz­aldehyde resulted in the formation of the imine title compound, C₁₅H₁₆N₂O₂S. In the crystal structure, mol­ecules are linked into chains through inter­molecular N—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.107
• Data-to-parameter ratio = 29.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio

   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

   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; 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.

4-Methyl-N'-[(E)-4-methylbenzylidene]benzenesulfonohydrazide

Crystal data

C15H16N2O2S	F(000) = 608
Mr = 288.36	Dx = 1.314 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7556 reflections
a = 5.3411 (2) Å	θ = 2.4–32.6°
b = 15.8299 (7) Å	µ = 0.23 mm^−1
c = 17.4133 (8) Å	T = 100 K
β = 98.034 (1)°	Prism, colourless
V = 1457.83 (11) Å^3	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	5374 independent reflections
Radiation source: fine-focus sealed tube	4457 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 32.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.957, Tmax = 0.978	k = −23→24
22219 measured reflections	l = −26→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.4173P] where P = (Fo^2 + 2Fc^2)/3
5374 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.42 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 > 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	0.81400 (4)	0.139684 (15)	0.173325 (14)	0.01480 (7)
O1	0.55203 (14)	0.14271 (5)	0.14027 (5)	0.02053 (16)
O2	0.92197 (15)	0.06283 (5)	0.20673 (5)	0.02014 (16)
N1	0.98293 (16)	0.16043 (6)	0.10328 (5)	0.01632 (16)
H1	1.1518	0.1481	0.1144	0.037 (5)*
N2	0.91427 (16)	0.23545 (5)	0.06373 (5)	0.01569 (16)
C1	1.07447 (19)	0.26500 (6)	0.02239 (6)	0.01531 (17)
H1A	1.2326	0.2376	0.0222	0.018*
C2	1.01422 (17)	0.34102 (6)	−0.02451 (5)	0.01337 (16)
C3	1.16403 (19)	0.36208 (6)	−0.08140 (6)	0.01589 (18)
H3A	1.3077	0.3286	−0.0874	0.019*
C4	1.10449 (19)	0.43170 (7)	−0.12935 (6)	0.01696 (18)
H4A	1.2077	0.4452	−0.1679	0.020*
C5	0.89491 (19)	0.48186 (6)	−0.12145 (6)	0.01591 (17)
C6	0.74691 (18)	0.46072 (6)	−0.06410 (6)	0.01566 (17)
H6A	0.6041	0.4945	−0.0579	0.019*
C7	0.80430 (18)	0.39152 (6)	−0.01619 (6)	0.01475 (17)
H7A	0.7011	0.3783	0.0224	0.018*
C8	0.8294 (2)	0.55743 (7)	−0.17298 (7)	0.0233 (2)
H8A	0.8285	0.5410	−0.2273	0.035*
H8B	0.9554	0.6020	−0.1595	0.035*
H8C	0.6618	0.5785	−0.1657	0.035*
C9	0.86901 (18)	0.22178 (6)	0.24170 (6)	0.01505 (17)
C10	1.09590 (19)	0.22267 (7)	0.29217 (6)	0.01809 (19)
H10A	1.2187	0.1797	0.2896	0.022*
C11	1.1394 (2)	0.28726 (7)	0.34617 (6)	0.0205 (2)
H11A	1.2945	0.2885	0.3803	0.025*
C12	0.9605 (2)	0.35060 (7)	0.35148 (7)	0.0212 (2)
C13	0.7354 (2)	0.34860 (7)	0.29994 (7)	0.0222 (2)
H13A	0.6123	0.3915	0.3025	0.027*
C14	0.68888 (19)	0.28479 (7)	0.24499 (6)	0.01874 (19)
H14A	0.5356	0.2842	0.2100	0.022*
C15	1.0114 (3)	0.41977 (8)	0.41112 (8)	0.0342 (3)
H15A	0.8509	0.4452	0.4203	0.051*
H15B	1.1186	0.4631	0.3921	0.051*
H15C	1.0977	0.3960	0.4597	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01243 (11)	0.01352 (11)	0.01846 (12)	0.00021 (7)	0.00222 (8)	0.00342 (8)
O1	0.0124 (3)	0.0215 (4)	0.0270 (4)	−0.0021 (3)	0.0004 (3)	0.0010 (3)
O2	0.0225 (4)	0.0141 (3)	0.0240 (4)	0.0026 (3)	0.0040 (3)	0.0052 (3)
N1	0.0145 (4)	0.0166 (4)	0.0182 (4)	0.0031 (3)	0.0032 (3)	0.0044 (3)
N2	0.0164 (4)	0.0150 (4)	0.0154 (4)	0.0011 (3)	0.0013 (3)	0.0025 (3)
C1	0.0147 (4)	0.0157 (4)	0.0154 (4)	0.0007 (3)	0.0016 (3)	−0.0006 (3)
C2	0.0123 (4)	0.0149 (4)	0.0129 (4)	−0.0012 (3)	0.0016 (3)	−0.0007 (3)
C3	0.0138 (4)	0.0179 (4)	0.0166 (4)	−0.0013 (3)	0.0044 (3)	−0.0017 (3)
C4	0.0175 (4)	0.0196 (4)	0.0144 (4)	−0.0043 (3)	0.0043 (3)	−0.0005 (3)
C5	0.0170 (4)	0.0155 (4)	0.0143 (4)	−0.0041 (3)	−0.0008 (3)	0.0001 (3)
C6	0.0134 (4)	0.0161 (4)	0.0173 (4)	−0.0003 (3)	0.0017 (3)	0.0000 (3)
C7	0.0130 (4)	0.0167 (4)	0.0149 (4)	−0.0006 (3)	0.0031 (3)	0.0000 (3)
C8	0.0280 (5)	0.0201 (5)	0.0205 (5)	−0.0032 (4)	−0.0010 (4)	0.0057 (4)
C9	0.0133 (4)	0.0149 (4)	0.0171 (4)	0.0005 (3)	0.0028 (3)	0.0039 (3)
C10	0.0147 (4)	0.0187 (4)	0.0203 (5)	0.0020 (3)	0.0006 (3)	0.0048 (3)
C11	0.0205 (5)	0.0195 (5)	0.0202 (5)	−0.0011 (4)	−0.0025 (4)	0.0047 (4)
C12	0.0267 (5)	0.0164 (4)	0.0199 (5)	−0.0005 (4)	0.0007 (4)	0.0033 (3)
C13	0.0224 (5)	0.0177 (5)	0.0263 (5)	0.0044 (4)	0.0025 (4)	0.0010 (4)
C14	0.0147 (4)	0.0181 (4)	0.0230 (5)	0.0023 (3)	0.0010 (3)	0.0025 (4)
C15	0.0479 (8)	0.0226 (6)	0.0291 (6)	0.0020 (5)	−0.0056 (6)	−0.0040 (5)

Geometric parameters (Å, º)

S1—O2	1.4344 (8)	C7—H7A	0.9500
S1—O1	1.4374 (8)	C8—H8A	0.9800
S1—N1	1.6484 (9)	C8—H8B	0.9800
S1—C9	1.7593 (11)	C8—H8C	0.9800
N1—N2	1.3960 (12)	C9—C14	1.3925 (14)
N1—H1	0.9165	C9—C10	1.3941 (14)
N2—C1	1.2811 (13)	C10—C11	1.3866 (15)
C1—C2	1.4647 (13)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.3971 (16)
C2—C3	1.3980 (13)	C11—H11A	0.9500
C2—C7	1.4009 (13)	C12—C13	1.3965 (16)
C3—C4	1.3924 (14)	C12—C15	1.5075 (17)
C3—H3A	0.9500	C13—C14	1.3896 (16)
C4—C5	1.3948 (14)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.3982 (14)	C15—H15A	0.9800
C5—C8	1.5069 (14)	C15—H15B	0.9800
C6—C7	1.3852 (14)	C15—H15C	0.9800
C6—H6A	0.9500
O2—S1—O1	120.29 (5)	C5—C8—H8A	109.5
O2—S1—N1	103.79 (5)	C5—C8—H8B	109.5
O1—S1—N1	107.45 (5)	H8A—C8—H8B	109.5
O2—S1—C9	109.42 (5)	C5—C8—H8C	109.5
O1—S1—C9	107.91 (5)	H8A—C8—H8C	109.5
N1—S1—C9	107.26 (5)	H8B—C8—H8C	109.5
N2—N1—S1	113.66 (7)	C14—C9—C10	120.77 (10)
N2—N1—H1	117.9	C14—C9—S1	120.40 (8)
S1—N1—H1	115.2	C10—C9—S1	118.84 (8)
C1—N2—N1	115.96 (8)	C11—C10—C9	118.91 (9)
N2—C1—C2	120.09 (9)	C11—C10—H10A	120.5
N2—C1—H1A	120.0	C9—C10—H10A	120.5
C2—C1—H1A	120.0	C10—C11—C12	121.51 (10)
C3—C2—C7	118.87 (9)	C10—C11—H11A	119.2
C3—C2—C1	119.22 (9)	C12—C11—H11A	119.2
C7—C2—C1	121.86 (9)	C13—C12—C11	118.46 (10)
C4—C3—C2	120.55 (9)	C13—C12—C15	121.02 (11)
C4—C3—H3A	119.7	C11—C12—C15	120.51 (11)
C2—C3—H3A	119.7	C14—C13—C12	120.93 (10)
C3—C4—C5	120.71 (9)	C14—C13—H13A	119.5
C3—C4—H4A	119.6	C12—C13—H13A	119.5
C5—C4—H4A	119.6	C13—C14—C9	119.40 (10)
C4—C5—C6	118.41 (9)	C13—C14—H14A	120.3
C4—C5—C8	121.06 (9)	C9—C14—H14A	120.3
C6—C5—C8	120.53 (9)	C12—C15—H15A	109.5
C7—C6—C5	121.33 (9)	C12—C15—H15B	109.5
C7—C6—H6A	119.3	H15A—C15—H15B	109.5
C5—C6—H6A	119.3	C12—C15—H15C	109.5
C6—C7—C2	120.13 (9)	H15A—C15—H15C	109.5
C6—C7—H7A	119.9	H15B—C15—H15C	109.5
C2—C7—H7A	119.9
O2—S1—N1—N2	−178.10 (7)	O2—S1—C9—C14	−144.65 (8)
O1—S1—N1—N2	53.47 (8)	O1—S1—C9—C14	−12.12 (10)
C9—S1—N1—N2	−62.34 (8)	N1—S1—C9—C14	103.37 (9)
S1—N1—N2—C1	163.71 (8)	O2—S1—C9—C10	35.54 (9)
N1—N2—C1—C2	176.81 (8)	O1—S1—C9—C10	168.06 (8)
N2—C1—C2—C3	−166.37 (9)	N1—S1—C9—C10	−76.44 (9)
N2—C1—C2—C7	10.99 (14)	C14—C9—C10—C11	0.28 (15)
C7—C2—C3—C4	−0.48 (14)	S1—C9—C10—C11	−179.91 (8)
C1—C2—C3—C4	176.97 (9)	C9—C10—C11—C12	0.64 (16)
C2—C3—C4—C5	0.17 (15)	C10—C11—C12—C13	−1.04 (17)
C3—C4—C5—C6	0.24 (15)	C10—C11—C12—C15	179.50 (11)
C3—C4—C5—C8	179.86 (9)	C11—C12—C13—C14	0.53 (17)
C4—C5—C6—C7	−0.34 (15)	C15—C12—C13—C14	179.99 (11)
C8—C5—C6—C7	−179.97 (9)	C12—C13—C14—C9	0.36 (17)
C5—C6—C7—C2	0.03 (15)	C10—C9—C14—C13	−0.77 (16)
C3—C2—C7—C6	0.38 (14)	S1—C9—C14—C13	179.42 (8)
C1—C2—C7—C6	−177.00 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1	0.95	2.56	2.9233 (14)	103
N1—H1···O1^i	0.92	2.12	3.0308 (12)	170

Symmetry code: (i) x+1, y, z.