N′-[(1E,2E)-1-(2-Phenyl­hydrazin-1-yl­idene)-1-(phenyl­sulfon­yl)propan-2-yl­idene]benzohydrazide

Abdel-Aziz, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811031953

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2317-o2318

doi:10.1107/S1600536811031953

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N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide

Hatem A. Abdel-Aziz,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 August 2011; accepted 7 August 2011; online 11 August 2011)

The configuration about each C=N bond in the title compound, C₂₂H₂₀N₄O₃S, is E. While to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are coplanar, in part due to the presence of an intramolecular 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 molecule [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 supramolecular chains via C—H⋯O interactions which are, in turn, linked into layers in the ac plane via C—H⋯π interactions. 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_r = 420.48
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.04
3942 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) x+1, y+1, z; (iii) -x+1, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031953/hb6353sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811031953/hb6353Isup3.cml

checkCIF report

Comment top

The title compound (I) was characterized in relation to on-going studies of bis-hydrazone derivatives which have been investigated for biological activity (Abdel-Aziz & Mekawey, 2009; Abdel-Aziz et al., 2010). The molecular structure of (I), Fig. 1, shows an E configuration about each of the C═N bonds [C7═N1 = 1.3130 (16) Å and C14═N3 = 1.2936 (17) Å]. The presence of an intramolecular N—H···N hydrogen bond closes a S(6) ring, {···HNNCCN}, and provides stabilization to the approximately co-planar arrangement between the phenylhydrazin-1-ylidene and benzohydrazide residues. This co-planarity does not extend to the hydrazine-benzene ring [the N1—N2—C8—C9 torsion angle is -170.74 (11) Å] nor to the benzoyl-benzene [N4—C16—C17—C18 = -21.72 (18) °] ring as significant twists are evident. Nevertheless, to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are co-planar and the sulfonyl-benzene occupies a position almost perpendicular to this plane as seen in the value of the C1—S1—C7—N1 torsion angle of -92.28 (10) °.

In the crystal packing, N—H···O hydrogen bonding between hydrazide-H and a sulfonyl-O leads to the formation of centrosymmetric aggregates via a 14-membered {···HNNC₂SO}₂ synthon, Table 1. These are connected into a linear supramolecular chain via C—H···O interactions, Table 1 and Fig. 2. The chains are connected into layers in the ac plane via C—H···π interactions, Table 1. Layers are connected along the b direction via π–π interactions occurring between centrosymmetrically related hydrazine-bound benzene rings [3.7425 (9) Å for symmetry operation: -x, -y, -z].

Related literature top

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

Experimental top

The title compound was prepared by the literature procedure (Abdel-Aziz et al., 2010) and yellow prisms were isolated from its solution in EtOH/DMF (v/v = 5/1) by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chain in (I) mediated by N—H···O hydrogen bonds (blue dashed lines), leading to centrosymmetric aggregates, and C—H···O interactions, shown as orange lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The N—H···O, C—H···O, C—H···π and π–π interactions are shown as blue, orange, purple and pink dashed lines, respectively.

N'-[(1E,2E)-1-(2-phenylhydrazin-1-ylidene)- 1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide top

Crystal data top

C₂₂H₂₀N₄O₃S	Z = 2
M_r = 420.48	F(000) = 440
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.017
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.2°
ω scans	h = −10→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→11
T_min = 0.825, T_max = 1.000	l = −17→15
6674 measured reflections

Refinement top

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(F_o²) + (0.0484P)² + 0.3295P] where P = (F_o² + 2F_c²)/3
3942 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₂H₂₀N₄O₃S	γ = 111.984 (4)°
M_r = 420.48	V = 998.55 (8) Å³
Triclinic, P1	Z = 2
a = 8.1609 (3) Å	Cu Kα radiation
b = 9.6632 (5) Å	µ = 1.72 mm⁻¹
c = 14.1261 (7) Å	T = 100 K
α = 92.027 (4)°	0.30 × 0.25 × 0.05 mm
β = 102.822 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3942 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3658 reflections with I > 2σ(I)
T_min = 0.825, T_max = 1.000	R_int = 0.017
6674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.34 e Å⁻³
3942 reflections	Δρ_min = −0.42 e Å⁻³
280 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₄O₃S
M_r	420.48
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1609 (3), 9.6632 (5), 14.1261 (7)
α, β, γ (°)	92.027 (4), 102.822 (4), 111.984 (4)
V (Å³)	998.55 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.30 × 0.25 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.825, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6674, 3942, 3658
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.04
No. of reflections	3942
No. of parameters	280
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.42

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) −x+1, −y, −z+1.

Footnotes

‡Additional correspondence author, e-mail: hatem_741@yahoo.com.

Acknowledgements

The authors thank King Saud University and the University of Malaya for supporting this study.

References

Abdel-Aziz, H. A., Abdel-Wahab, B. F. & Badria, F. A. (2010). Arch. Pharm. 343, 152–159. Google Scholar
Abdel-Aziz, H. A. & Mekawey, A. A. I. (2009). Eur. J. Med. Chem. 44, 3985–4997. Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Pages o2317-o2318

doi:10.1107/S1600536811031953

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(1E,2E)-1-(2-Phenyl­hydrazin-1-yl­­idene)-1-(phenyl­sulfon­yl)propan-2-yl­­idene]benzohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide