N'-[(1E,2E)-1-(2-Phenyl-hydrazin-1-yl-idene)-1-(phenyl-sulfon-yl)propan-2-yl-idene]benzohydrazide.

The configuration about each C=N bond in the title compound, C(22)H(20)N(4)O(3)S, is E. While to a first approximation the phenyl-hydrazin-1-yl-idene and benzohydrazide residues are coplanar, in part due to the presence of an intra-molecular N-H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N-N-C-C torsion angle = -170.74 (11)°] and benzoyl benzene [N-C-C-C = -21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the mol-ecule [C-S-C-N = -92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide-sulfonyl N-H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supra-molecular chains via C-H⋯O inter-actions which are, in turn, linked into layers in the ac plane via C-H⋯π inter-actions. Connections between layers along the b-axis direction are of the π-π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid-centroid separation = 3.7425 (9) Å].

Related literature

For background to the biological activity of bis-hydrazones, see: Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶).

Experimental

Crystal data

C22H20N4O3S

M = 420.48

Triclinic,

a = 8.1609 (3) Å

b = 9.6632 (5) Å

c = 14.1261 (7) Å

α = 92.027 (4)°

β = 102.822 (4)°

γ = 111.984 (4)°

V = 998.55 (8) Å3

Z = 2

Cu Kα radiation

μ = 1.72 mm−1

T = 100 K

0.30 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.825, T max = 1.000

6674 measured reflections

3942 independent reflections

3658 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.04

3942 reflections

280 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031953/hb6353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031953/hb6353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031953/hb6353Isup3.cml

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

C22H20N4O3S	Z = 2
Mr = 420.48	F(000) = 440
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 8.1609 (3) Å	Cell parameters from 4430 reflections
b = 9.6632 (5) Å	θ = 3.2–74.2°
c = 14.1261 (7) Å	µ = 1.72 mm−1
α = 92.027 (4)°	T = 100 K
β = 102.822 (4)°	Prism, yellow
γ = 111.984 (4)°	0.30 × 0.25 × 0.05 mm
V = 998.55 (8) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3942 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3658 reflections with I > 2σ(I)
mirror	Rint = 0.017
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.2°
ω scans	h = −10→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→11
Tmin = 0.825, Tmax = 1.000	l = −17→15
6674 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.3295P] where P = (Fo2 + 2Fc2)/3
3942 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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
S1	0.50233 (4)	0.56979 (3)	0.25827 (2)	0.01376 (10)
O1	0.58750 (13)	0.66428 (10)	0.35165 (7)	0.0188 (2)
O2	0.38284 (12)	0.61117 (10)	0.18465 (7)	0.0184 (2)
O3	0.10801 (14)	−0.07033 (11)	0.38899 (7)	0.0272 (2)
N1	0.24156 (14)	0.31176 (12)	0.20702 (8)	0.0156 (2)
N2	0.12879 (15)	0.17365 (12)	0.20937 (8)	0.0162 (2)
H2	0.146 (2)	0.134 (2)	0.2655 (14)	0.031 (5)*
N3	0.31255 (14)	0.20873 (12)	0.38694 (8)	0.0157 (2)
N4	0.34253 (15)	0.14291 (12)	0.46998 (8)	0.0155 (2)
H4	0.393 (2)	0.196 (2)	0.5262 (13)	0.024 (4)*
C1	0.67600 (17)	0.55617 (14)	0.20755 (9)	0.0142 (2)
C2	0.85772 (17)	0.62654 (14)	0.25910 (9)	0.0172 (3)
H2A	0.8906	0.6826	0.3218	0.021*
C3	0.99099 (18)	0.61328 (15)	0.21697 (10)	0.0202 (3)
H3	1.1162	0.6608	0.2512	0.024*
C4	0.94206 (18)	0.53115 (16)	0.12537 (10)	0.0204 (3)
H4A	1.0337	0.5217	0.0975	0.025*
C5	0.75863 (18)	0.46236 (15)	0.07400 (9)	0.0190 (3)
H5	0.7258	0.4071	0.0110	0.023*
C6	0.62441 (17)	0.47453 (14)	0.11483 (9)	0.0162 (3)
H6	0.4993	0.4281	0.0803	0.019*
C7	0.38026 (17)	0.38545 (14)	0.28212 (9)	0.0147 (2)
C8	−0.02363 (17)	0.09899 (14)	0.12996 (9)	0.0157 (3)
C9	−0.15086 (18)	−0.03770 (14)	0.14394 (9)	0.0183 (3)
H9	−0.1313	−0.0773	0.2041	0.022*
C10	−0.30598 (19)	−0.11519 (15)	0.06928 (10)	0.0210 (3)
H10	−0.3932	−0.2084	0.0783	0.025*
C11	−0.33482 (19)	−0.05745 (16)	−0.01863 (10)	0.0224 (3)
H11	−0.4418	−0.1105	−0.0695	0.027*
C12	−0.2058 (2)	0.07881 (16)	−0.03178 (10)	0.0228 (3)
H12	−0.2252	0.1180	−0.0921	0.027*
C13	−0.04996 (18)	0.15771 (15)	0.04185 (10)	0.0188 (3)
H13	0.0377	0.2504	0.0325	0.023*
C14	0.43798 (17)	0.33214 (14)	0.37516 (9)	0.0147 (2)
C15	0.62412 (17)	0.40633 (14)	0.44494 (9)	0.0173 (3)
H15A	0.6634	0.3290	0.4728	0.026*
H15B	0.6187	0.4718	0.4978	0.026*
H15C	0.7114	0.4665	0.4098	0.026*
C16	0.21874 (18)	−0.00233 (14)	0.46522 (9)	0.0171 (3)
C17	0.23417 (18)	−0.07141 (14)	0.55775 (9)	0.0166 (3)
C18	0.39363 (19)	−0.02070 (15)	0.63346 (10)	0.0190 (3)
H18	0.4977	0.0635	0.6283	0.023*
C19	0.4000 (2)	−0.09350 (16)	0.71628 (10)	0.0236 (3)
H19	0.5090	−0.0598	0.7676	0.028*
C20	0.2473 (2)	−0.21564 (16)	0.72444 (10)	0.0247 (3)
H20	0.2516	−0.2643	0.7816	0.030*
C21	0.0886 (2)	−0.26655 (16)	0.64928 (11)	0.0231 (3)
H21	−0.0154	−0.3503	0.6549	0.028*
C22	0.08182 (18)	−0.19513 (15)	0.56582 (10)	0.0195 (3)
H22	−0.0267	−0.2305	0.5141	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.01522 (16)	0.01194 (15)	0.01440 (16)	0.00461 (12)	0.00554 (11)	0.00199 (11)
O1	0.0231 (5)	0.0151 (4)	0.0175 (4)	0.0056 (4)	0.0075 (4)	−0.0008 (3)
O2	0.0183 (4)	0.0180 (4)	0.0211 (5)	0.0086 (4)	0.0063 (4)	0.0066 (4)
O3	0.0318 (6)	0.0185 (5)	0.0178 (5)	−0.0002 (4)	−0.0017 (4)	0.0018 (4)
N1	0.0164 (5)	0.0142 (5)	0.0161 (5)	0.0047 (4)	0.0061 (4)	0.0012 (4)
N2	0.0176 (5)	0.0140 (5)	0.0140 (5)	0.0028 (4)	0.0039 (4)	0.0020 (4)
N3	0.0182 (5)	0.0158 (5)	0.0136 (5)	0.0067 (4)	0.0049 (4)	0.0036 (4)
N4	0.0185 (5)	0.0142 (5)	0.0114 (5)	0.0044 (4)	0.0027 (4)	0.0020 (4)
C1	0.0167 (6)	0.0124 (6)	0.0147 (6)	0.0053 (5)	0.0063 (5)	0.0048 (5)
C2	0.0182 (6)	0.0151 (6)	0.0153 (6)	0.0035 (5)	0.0039 (5)	0.0014 (5)
C3	0.0145 (6)	0.0206 (6)	0.0229 (7)	0.0037 (5)	0.0046 (5)	0.0046 (5)
C4	0.0203 (6)	0.0234 (7)	0.0215 (7)	0.0097 (5)	0.0103 (5)	0.0069 (5)
C5	0.0228 (7)	0.0206 (7)	0.0141 (6)	0.0082 (5)	0.0060 (5)	0.0026 (5)
C6	0.0162 (6)	0.0163 (6)	0.0150 (6)	0.0054 (5)	0.0031 (5)	0.0036 (5)
C7	0.0154 (6)	0.0131 (6)	0.0155 (6)	0.0044 (5)	0.0060 (5)	0.0018 (5)
C8	0.0168 (6)	0.0146 (6)	0.0147 (6)	0.0057 (5)	0.0036 (5)	−0.0002 (5)
C9	0.0212 (6)	0.0170 (6)	0.0153 (6)	0.0059 (5)	0.0042 (5)	0.0035 (5)
C10	0.0198 (6)	0.0173 (6)	0.0208 (7)	0.0021 (5)	0.0045 (5)	0.0016 (5)
C11	0.0214 (7)	0.0211 (7)	0.0179 (6)	0.0042 (5)	−0.0005 (5)	0.0003 (5)
C12	0.0270 (7)	0.0222 (7)	0.0169 (6)	0.0084 (6)	0.0029 (5)	0.0047 (5)
C13	0.0215 (6)	0.0157 (6)	0.0176 (6)	0.0050 (5)	0.0060 (5)	0.0031 (5)
C14	0.0162 (6)	0.0144 (6)	0.0147 (6)	0.0065 (5)	0.0054 (5)	0.0007 (5)
C15	0.0170 (6)	0.0169 (6)	0.0175 (6)	0.0060 (5)	0.0046 (5)	0.0014 (5)
C16	0.0187 (6)	0.0147 (6)	0.0168 (6)	0.0054 (5)	0.0046 (5)	0.0016 (5)
C17	0.0212 (6)	0.0147 (6)	0.0169 (6)	0.0091 (5)	0.0068 (5)	0.0029 (5)
C18	0.0227 (7)	0.0171 (6)	0.0180 (6)	0.0085 (5)	0.0058 (5)	0.0024 (5)
C19	0.0311 (7)	0.0259 (7)	0.0167 (6)	0.0155 (6)	0.0038 (5)	0.0034 (5)
C20	0.0389 (8)	0.0258 (7)	0.0202 (7)	0.0203 (6)	0.0143 (6)	0.0102 (6)
C21	0.0283 (7)	0.0202 (7)	0.0297 (7)	0.0128 (6)	0.0175 (6)	0.0102 (6)
C22	0.0206 (6)	0.0179 (6)	0.0230 (7)	0.0090 (5)	0.0087 (5)	0.0046 (5)

S1—O2	1.4365 (9)	C8—C9	1.3945 (18)
S1—O1	1.4456 (9)	C9—C10	1.3847 (18)
S1—C1	1.7672 (13)	C9—H9	0.9500
S1—C7	1.7725 (13)	C10—C11	1.3880 (19)
O3—C16	1.2172 (16)	C10—H10	0.9500
N1—C7	1.3130 (16)	C11—C12	1.394 (2)
N1—N2	1.3139 (15)	C11—H11	0.9500
N2—C8	1.4062 (16)	C12—C13	1.3826 (19)
N2—H2	0.901 (19)	C12—H12	0.9500
N3—C14	1.2936 (17)	C13—H13	0.9500
N3—N4	1.3720 (15)	C14—C15	1.5044 (17)
N4—C16	1.3771 (16)	C15—H15A	0.9800
N4—H4	0.856 (18)	C15—H15B	0.9800
C1—C2	1.3866 (18)	C15—H15C	0.9800
C1—C6	1.3960 (18)	C16—C17	1.4905 (17)
C2—C3	1.3927 (19)	C17—C18	1.3947 (18)
C2—H2A	0.9500	C17—C22	1.3956 (18)
C3—C4	1.3872 (19)	C18—C19	1.3875 (19)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.3957 (19)	C19—C20	1.390 (2)
C4—H4A	0.9500	C19—H19	0.9500
C5—C6	1.3849 (18)	C20—C21	1.386 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.3881 (19)
C7—C14	1.4729 (17)	C21—H21	0.9500
C8—C13	1.3928 (18)	C22—H22	0.9500
O2—S1—O1	118.61 (6)	C9—C10—H10	119.8
O2—S1—C1	107.72 (6)	C11—C10—H10	119.8
O1—S1—C1	108.38 (6)	C10—C11—C12	119.60 (12)
O2—S1—C7	108.78 (6)	C10—C11—H11	120.2
O1—S1—C7	107.22 (6)	C12—C11—H11	120.2
C1—S1—C7	105.38 (6)	C13—C12—C11	120.86 (12)
C7—N1—N2	121.00 (11)	C13—C12—H12	119.6
N1—N2—C8	120.16 (11)	C11—C12—H12	119.6
N1—N2—H2	117.7 (11)	C12—C13—C8	118.89 (12)
C8—N2—H2	121.8 (11)	C12—C13—H13	120.6
C14—N3—N4	119.70 (11)	C8—C13—H13	120.6
N3—N4—C16	114.32 (10)	N3—C14—C7	111.66 (11)
N3—N4—H4	120.7 (12)	N3—C14—C15	123.98 (11)
C16—N4—H4	118.2 (12)	C7—C14—C15	124.24 (11)
C2—C1—C6	121.75 (12)	C14—C15—H15A	109.5
C2—C1—S1	120.14 (10)	C14—C15—H15B	109.5
C6—C1—S1	118.11 (9)	H15A—C15—H15B	109.5
C1—C2—C3	118.60 (12)	C14—C15—H15C	109.5
C1—C2—H2A	120.7	H15A—C15—H15C	109.5
C3—C2—H2A	120.7	H15B—C15—H15C	109.5
C4—C3—C2	120.42 (12)	O3—C16—N4	121.44 (12)
C4—C3—H3	119.8	O3—C16—C17	122.71 (12)
C2—C3—H3	119.8	N4—C16—C17	115.81 (11)
C3—C4—C5	120.25 (12)	C18—C17—C22	119.76 (12)
C3—C4—H4A	119.9	C18—C17—C16	122.99 (12)
C5—C4—H4A	119.9	C22—C17—C16	117.22 (12)
C6—C5—C4	120.05 (12)	C19—C18—C17	119.85 (13)
C6—C5—H5	120.0	C19—C18—H18	120.1
C4—C5—H5	120.0	C17—C18—H18	120.1
C5—C6—C1	118.92 (12)	C18—C19—C20	120.18 (13)
C5—C6—H6	120.5	C18—C19—H19	119.9
C1—C6—H6	120.5	C20—C19—H19	119.9
N1—C7—C14	128.30 (11)	C21—C20—C19	120.14 (13)
N1—C7—S1	110.37 (9)	C21—C20—H20	119.9
C14—C7—S1	121.33 (9)	C19—C20—H20	119.9
C13—C8—C9	120.90 (12)	C20—C21—C22	120.00 (13)
C13—C8—N2	122.56 (11)	C20—C21—H21	120.0
C9—C8—N2	116.54 (11)	C22—C21—H21	120.0
C10—C9—C8	119.36 (12)	C21—C22—C17	120.06 (13)
C10—C9—H9	120.3	C21—C22—H22	120.0
C8—C9—H9	120.3	C17—C22—H22	120.0
C9—C10—C11	120.39 (12)
C7—N1—N2—C8	177.15 (11)	N2—C8—C9—C10	178.61 (12)
C14—N3—N4—C16	−166.62 (11)	C8—C9—C10—C11	−0.1 (2)
O2—S1—C1—C2	131.46 (10)	C9—C10—C11—C12	0.5 (2)
O1—S1—C1—C2	1.97 (12)	C10—C11—C12—C13	−0.4 (2)
C7—S1—C1—C2	−112.54 (11)	C11—C12—C13—C8	−0.1 (2)
O2—S1—C1—C6	−47.94 (11)	C9—C8—C13—C12	0.6 (2)
O1—S1—C1—C6	−177.43 (9)	N2—C8—C13—C12	−178.46 (12)
C7—S1—C1—C6	68.06 (11)	N4—N3—C14—C7	−179.77 (10)
C6—C1—C2—C3	−0.71 (19)	N4—N3—C14—C15	3.87 (18)
S1—C1—C2—C3	179.92 (10)	N1—C7—C14—N3	−13.99 (19)
C1—C2—C3—C4	0.0 (2)	S1—C7—C14—N3	166.60 (9)
C2—C3—C4—C5	0.7 (2)	N1—C7—C14—C15	162.36 (12)
C3—C4—C5—C6	−0.7 (2)	S1—C7—C14—C15	−17.05 (17)
C4—C5—C6—C1	−0.05 (19)	N3—N4—C16—O3	8.74 (18)
C2—C1—C6—C5	0.75 (19)	N3—N4—C16—C17	−173.41 (10)
S1—C1—C6—C5	−179.86 (10)	O3—C16—C17—C18	156.10 (13)
N2—N1—C7—C14	2.3 (2)	N4—C16—C17—C18	−21.72 (18)
N2—N1—C7—S1	−178.25 (9)	O3—C16—C17—C22	−21.95 (19)
O2—S1—C7—N1	22.99 (11)	N4—C16—C17—C22	160.23 (12)
O1—S1—C7—N1	152.40 (9)	C22—C17—C18—C19	0.04 (19)
C1—S1—C7—N1	−92.28 (10)	C16—C17—C18—C19	−177.96 (12)
O2—S1—C7—C14	−157.51 (10)	C17—C18—C19—C20	−0.7 (2)
O1—S1—C7—C14	−28.10 (11)	C18—C19—C20—C21	0.9 (2)
C1—S1—C7—C14	87.22 (11)	C19—C20—C21—C22	−0.3 (2)
N1—N2—C8—C13	8.35 (19)	C20—C21—C22—C17	−0.4 (2)
N1—N2—C8—C9	−170.74 (11)	C18—C17—C22—C21	0.54 (19)
C13—C8—C9—C10	−0.5 (2)	C16—C17—C22—C21	178.65 (12)

Cg1 and Cg2 are the centroids of the C1—C6 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3	0.901 (19)	1.860 (18)	2.5584 (15)	132.8 (16)
N4—H4···O1i	0.856 (18)	2.089 (19)	2.8946 (14)	156.4 (16)
C2—H2a···O3ii	0.95	2.38	3.0977 (16)	132
C20—H20···Cg1iii	0.95	2.72	3.4980 (15)	140
C15—H15a···Cg2iii	0.98	2.79	3.4052 (15)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1—C6 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3	0.901 (19)	1.860 (18)	2.5584 (15)	132.8 (16)
N4—H4⋯O1i	0.856 (18)	2.089 (19)	2.8946 (14)	156.4 (16)
C2—H2a⋯O3ii	0.95	2.38	3.0977 (16)	132
C20—H20⋯Cg1iii	0.95	2.72	3.4980 (15)	140
C15—H15a⋯Cg2iii	0.98	2.79	3.4052 (15)	121

Symmetry codes: (i) ; (ii) ; (iii) .