Crystal structure of N'-[(E)-(4-chloro-phen-yl)(phen-yl)methyl-idene]-4-methyl-benzene-sulfono-hydrazide.

The title compound, C20H17ClN2O2S, was obtained by a condensation reaction between 4-chloro-benzo-phenone and tosyl hydrazide. The plane of the methyl-substituted benzene ring forms dihedral angles of 20.12 (12) and 78.43 (13)° with those of the chlorine-substituted benzene ring and the benzene ring, respectively, with the last two rings forming a dihedral angle of 67.81 (13)°. The chlorine substituent was also found to be 0.868 (2):0.132 (2) disordered over these two rings. In the crystal, mol-ecules are linked through pairs of N-H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R 2 (2)(8)], which are linked by weak C-H⋯O and C-H⋯Cl inter-actions into a chain structure which extends along the a-axis direction.

Related literature

Benzo­phenone and its derivatives have been investigated extensively for their biological activities such as anti-fungal and anti-inflammatory, see: Khanum et al. (2004 ▸). For similar structures, see: Ajani et al. (2010 ▸); Gerdemann et al. (2002 ▸); Kutzke et al. (2000 ▸); Shen et al. (2012 ▸); Zhang (2011 ▸).

Experimental

Crystal data

C20H17ClN2O2S

M = 384.87

Monoclinic,

a = 12.6808 (6) Å

b = 9.3857 (5) Å

c = 16.3974 (7) Å

β = 106.187 (2)°

V = 1874.22 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.891, T max = 0.930

21401 measured reflections

3300 independent reflections

2416 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.06

3300 reflections

253 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989014026723/zs2319sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026723/zs2319Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014026723/zs2319Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014026723/zs2319fig1.tif

The mol­ecular structure of the title compound showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level

Click here for additional data file.

. DOI: 10.1107/S2056989014026723/zs2319fig2.tif

A view of the crystal packing of the title compound. The various hydrogen bonds are indicated by dashed lines (see Table 1 for details).

CCDC reference: 1037752

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H17ClN2O2S	F(000) = 800
Mr = 384.87	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6873 reflections
a = 12.6808 (6) Å	θ = 2.5–25.2°
b = 9.3857 (5) Å	µ = 0.33 mm−1
c = 16.3974 (7) Å	T = 293 K
β = 106.187 (2)°	Block, brown
V = 1874.22 (16) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3300 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.891, Tmax = 0.930	k = −11→11
21401 measured reflections	l = −18→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0351P)2 + 1.1726P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3300 reflections	Δρmax = 0.35 e Å−3
253 parameters	Δρmin = −0.33 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (7)

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	Occ. (<1)
C1	0.6473 (2)	0.5896 (3)	0.50383 (16)	0.0567 (7)
H1	0.5830	0.6014	0.5198	0.068*
C2	0.6980 (3)	0.4588 (3)	0.51169 (18)	0.0650 (8)
H2	0.6676	0.3825	0.5334	0.078*
C3	0.7928 (3)	0.4383 (3)	0.48812 (18)	0.0632 (7)
C4	0.8369 (2)	0.5531 (3)	0.45737 (17)	0.0612 (7)
H4	0.9013	0.5410	0.4416	0.073*
C5	0.7885 (2)	0.6855 (3)	0.44933 (16)	0.0510 (6)
H5	0.8200	0.7621	0.4288	0.061*
C6	0.69263 (19)	0.7028 (3)	0.47211 (14)	0.0445 (6)
C7	0.81124 (18)	1.0259 (2)	0.65813 (15)	0.0430 (6)
C8	0.73683 (18)	1.0797 (3)	0.70683 (14)	0.0429 (6)
C9	0.7223 (2)	1.2238 (3)	0.71776 (16)	0.0511 (6)
H9	0.7612	1.2898	0.6953	0.061*
C10	0.6505 (2)	1.2706 (3)	0.76179 (17)	0.0581 (7)
H10	0.6405	1.3675	0.7691	0.070*
C11	0.5943 (2)	1.1708 (3)	0.79449 (16)	0.0587 (7)
C12	0.6081 (2)	1.0282 (3)	0.78491 (17)	0.0605 (7)
H12	0.5692	0.9624	0.8077	0.073*
C13	0.6794 (2)	0.9831 (3)	0.74156 (15)	0.0525 (6)
H13	0.6895	0.8859	0.7353	0.063*
C14	0.93096 (18)	1.0480 (3)	0.68959 (15)	0.0453 (6)
C15	0.9995 (2)	1.0041 (3)	0.64206 (17)	0.0541 (7)
H15	0.9696	0.9608	0.5897	0.065*
C16	1.1112 (2)	1.0234 (3)	0.6711 (2)	0.0632 (8)
H16	1.1566	0.9927	0.6388	0.076*
C17	1.1549 (2)	1.0880 (3)	0.7477 (2)	0.0699 (9)
H17	1.2283 (17)	1.100 (4)	0.769 (2)	0.084*
C18	1.0896 (2)	1.1329 (3)	0.7961 (2)	0.0723 (8)
H18	1.1203	1.1770	0.8481	0.087*
C19	0.9777 (2)	1.1124 (3)	0.76732 (17)	0.0610 (7)
H19	0.9331	1.1421	0.8005	0.073*
C20	0.8462 (3)	0.2933 (4)	0.4951 (3)	0.1014 (12)
H20A	0.8929	0.2890	0.4580	0.152*
H20B	0.7905	0.2213	0.4791	0.152*
H20C	0.8893	0.2776	0.5526	0.152*
N1	0.66524 (16)	0.9315 (2)	0.55792 (13)	0.0548 (6)
N2	0.77696 (15)	0.9565 (2)	0.58850 (13)	0.0498 (5)
O1	0.67110 (15)	0.9520 (2)	0.40485 (12)	0.0639 (5)
O2	0.51226 (13)	0.8526 (2)	0.44334 (11)	0.0599 (5)
S1	0.62845 (5)	0.86959 (7)	0.46061 (4)	0.0477 (2)
Cl1	0.50538 (8)	1.22428 (12)	0.85037 (6)	0.0880 (4)	0.868 (2)
Cl1'	1.2814 (4)	1.1131 (6)	0.7865 (4)	0.0616 (19)	0.132 (2)
H1A	0.6174 (19)	0.988 (2)	0.5711 (16)	0.061 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0582 (16)	0.0650 (18)	0.0486 (15)	−0.0090 (14)	0.0175 (12)	−0.0045 (13)
C2	0.078 (2)	0.0537 (18)	0.0595 (17)	−0.0106 (15)	0.0136 (15)	0.0068 (14)
C3	0.073 (2)	0.0506 (17)	0.0568 (17)	0.0071 (14)	0.0038 (14)	0.0010 (14)
C4	0.0578 (17)	0.0611 (18)	0.0649 (18)	0.0115 (14)	0.0173 (14)	−0.0015 (14)
C5	0.0493 (15)	0.0498 (15)	0.0558 (16)	0.0009 (12)	0.0179 (12)	0.0001 (12)
C6	0.0467 (14)	0.0476 (14)	0.0371 (13)	−0.0008 (11)	0.0081 (11)	−0.0058 (11)
C7	0.0414 (13)	0.0402 (13)	0.0454 (14)	0.0014 (10)	0.0087 (11)	−0.0039 (11)
C8	0.0381 (12)	0.0476 (14)	0.0408 (13)	−0.0034 (10)	0.0072 (10)	−0.0069 (11)
C9	0.0473 (14)	0.0517 (15)	0.0577 (16)	−0.0038 (12)	0.0200 (12)	−0.0072 (12)
C10	0.0584 (16)	0.0554 (16)	0.0617 (17)	0.0062 (13)	0.0191 (14)	−0.0084 (14)
C11	0.0449 (15)	0.085 (2)	0.0483 (15)	0.0102 (14)	0.0167 (12)	0.0013 (15)
C12	0.0563 (16)	0.075 (2)	0.0517 (16)	−0.0085 (15)	0.0174 (13)	0.0071 (14)
C13	0.0557 (15)	0.0526 (15)	0.0478 (15)	−0.0043 (12)	0.0122 (12)	−0.0031 (12)
C14	0.0399 (13)	0.0422 (13)	0.0510 (15)	0.0005 (10)	0.0081 (11)	0.0014 (11)
C15	0.0471 (14)	0.0533 (16)	0.0627 (17)	0.0036 (12)	0.0165 (13)	0.0001 (13)
C16	0.0457 (15)	0.0585 (17)	0.088 (2)	0.0035 (13)	0.0225 (15)	0.0049 (16)
C17	0.0399 (15)	0.0563 (18)	0.104 (3)	−0.0040 (14)	0.0041 (17)	0.0068 (17)
C18	0.0513 (17)	0.073 (2)	0.078 (2)	−0.0055 (15)	−0.0058 (15)	−0.0135 (17)
C19	0.0481 (15)	0.0690 (18)	0.0612 (17)	−0.0013 (13)	0.0076 (13)	−0.0123 (15)
C20	0.122 (3)	0.059 (2)	0.114 (3)	0.022 (2)	0.018 (2)	0.010 (2)
N1	0.0370 (12)	0.0694 (15)	0.0555 (13)	0.0035 (10)	0.0089 (10)	−0.0248 (11)
N2	0.0361 (11)	0.0558 (13)	0.0544 (13)	0.0033 (9)	0.0071 (9)	−0.0145 (10)
O1	0.0688 (12)	0.0634 (12)	0.0642 (12)	0.0126 (10)	0.0262 (10)	0.0144 (10)
O2	0.0382 (9)	0.0772 (13)	0.0585 (11)	0.0056 (9)	0.0038 (8)	−0.0159 (10)
S1	0.0428 (3)	0.0552 (4)	0.0435 (4)	0.0046 (3)	0.0095 (3)	−0.0070 (3)
Cl1	0.0827 (7)	0.1092 (8)	0.0920 (7)	0.0402 (6)	0.0573 (6)	0.0216 (6)
Cl1'	0.044 (3)	0.065 (4)	0.067 (4)	−0.011 (3)	0.001 (2)	−0.003 (3)

C1—C2	1.375 (4)	C12—C13	1.364 (4)
C1—C6	1.378 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.374 (4)	C14—C15	1.382 (3)
C2—H2	0.9300	C14—C19	1.385 (3)
C3—C4	1.373 (4)	C15—C16	1.374 (4)
C3—C20	1.510 (4)	C15—H15	0.9300
C4—C5	1.376 (4)	C16—C17	1.366 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.377 (3)	C17—C18	1.363 (4)
C5—H5	0.9300	C17—Cl1'	1.570 (5)
C6—S1	1.750 (2)	C17—H17	0.905 (19)
C7—N2	1.281 (3)	C18—C19	1.378 (4)
C7—C14	1.476 (3)	C18—H18	0.9300
C7—C8	1.484 (3)	C19—H19	0.9300
C8—C13	1.382 (3)	C20—H20A	0.9600
C8—C9	1.383 (3)	C20—H20B	0.9600
C9—C10	1.382 (3)	C20—H20C	0.9600
C9—H9	0.9300	N1—N2	1.385 (3)
C10—C11	1.374 (4)	N1—S1	1.639 (2)
C10—H10	0.9300	N1—H1A	0.877 (17)
C11—C12	1.365 (4)	O1—S1	1.4150 (18)
C11—Cl1	1.714 (3)	O2—S1	1.4296 (17)
C2—C1—C6	119.4 (3)	C8—C13—H13	119.6
C2—C1—H1	120.3	C15—C14—C19	118.3 (2)
C6—C1—H1	120.3	C15—C14—C7	120.5 (2)
C3—C2—C1	121.4 (3)	C19—C14—C7	121.2 (2)
C3—C2—H2	119.3	C16—C15—C14	120.9 (3)
C1—C2—H2	119.3	C16—C15—H15	119.5
C4—C3—C2	118.1 (3)	C14—C15—H15	119.5
C4—C3—C20	120.9 (3)	C17—C16—C15	119.5 (3)
C2—C3—C20	120.9 (3)	C17—C16—H16	120.3
C3—C4—C5	121.8 (3)	C15—C16—H16	120.3
C3—C4—H4	119.1	C18—C17—C16	121.1 (3)
C5—C4—H4	119.1	C18—C17—Cl1'	115.9 (3)
C4—C5—C6	119.0 (2)	C16—C17—Cl1'	123.1 (3)
C4—C5—H5	120.5	C18—C17—H17	118 (3)
C6—C5—H5	120.5	C16—C17—H17	121 (2)
C5—C6—C1	120.2 (2)	C17—C18—C19	119.5 (3)
C5—C6—S1	119.72 (19)	C17—C18—H18	120.3
C1—C6—S1	120.04 (19)	C19—C18—H18	120.3
N2—C7—C14	116.3 (2)	C18—C19—C14	120.8 (3)
N2—C7—C8	122.9 (2)	C18—C19—H19	119.6
C14—C7—C8	120.7 (2)	C14—C19—H19	119.6
C13—C8—C9	118.9 (2)	C3—C20—H20A	109.5
C13—C8—C7	119.1 (2)	C3—C20—H20B	109.5
C9—C8—C7	122.0 (2)	H20A—C20—H20B	109.5
C10—C9—C8	120.6 (2)	C3—C20—H20C	109.5
C10—C9—H9	119.7	H20A—C20—H20C	109.5
C8—C9—H9	119.7	H20B—C20—H20C	109.5
C11—C10—C9	118.4 (3)	N2—N1—S1	113.42 (16)
C11—C10—H10	120.8	N2—N1—H1A	121.1 (18)
C9—C10—H10	120.8	S1—N1—H1A	115.2 (17)
C12—C11—C10	121.8 (2)	C7—N2—N1	117.89 (19)
C12—C11—Cl1	118.3 (2)	O1—S1—O2	119.43 (12)
C10—C11—Cl1	119.9 (2)	O1—S1—N1	112.27 (12)
C13—C12—C11	119.3 (3)	O2—S1—N1	103.31 (11)
C13—C12—H12	120.4	O1—S1—C6	107.96 (11)
C11—C12—H12	120.4	O2—S1—C6	110.15 (12)
C12—C13—C8	120.9 (3)	N1—S1—C6	102.39 (11)
C12—C13—H13	119.6
C6—C1—C2—C3	−0.4 (4)	C8—C7—C14—C15	−176.8 (2)
C1—C2—C3—C4	0.9 (4)	N2—C7—C14—C19	−175.2 (2)
C1—C2—C3—C20	−178.5 (3)	C8—C7—C14—C19	3.6 (4)
C2—C3—C4—C5	−0.5 (4)	C19—C14—C15—C16	0.1 (4)
C20—C3—C4—C5	179.0 (3)	C7—C14—C15—C16	−179.6 (2)
C3—C4—C5—C6	−0.5 (4)	C14—C15—C16—C17	−0.5 (4)
C4—C5—C6—C1	1.1 (4)	C15—C16—C17—C18	0.4 (5)
C4—C5—C6—S1	−178.9 (2)	C15—C16—C17—Cl1'	179.3 (3)
C2—C1—C6—C5	−0.7 (4)	C16—C17—C18—C19	0.2 (5)
C2—C1—C6—S1	179.3 (2)	Cl1'—C17—C18—C19	−178.8 (3)
N2—C7—C8—C13	64.3 (3)	C17—C18—C19—C14	−0.6 (5)
C14—C7—C8—C13	−114.3 (3)	C15—C14—C19—C18	0.5 (4)
N2—C7—C8—C9	−115.0 (3)	C7—C14—C19—C18	−179.8 (3)
C14—C7—C8—C9	66.4 (3)	C14—C7—N2—N1	178.9 (2)
C13—C8—C9—C10	−0.8 (4)	C8—C7—N2—N1	0.2 (4)
C7—C8—C9—C10	178.5 (2)	S1—N1—N2—C7	168.96 (19)
C8—C9—C10—C11	0.1 (4)	N2—N1—S1—O1	−50.0 (2)
C9—C10—C11—C12	0.4 (4)	N2—N1—S1—O2	−179.99 (18)
C9—C10—C11—Cl1	179.4 (2)	N2—N1—S1—C6	65.5 (2)
C10—C11—C12—C13	−0.1 (4)	C5—C6—S1—O1	17.3 (2)
Cl1—C11—C12—C13	−179.2 (2)	C1—C6—S1—O1	−162.68 (19)
C11—C12—C13—C8	−0.6 (4)	C5—C6—S1—O2	149.31 (19)
C9—C8—C13—C12	1.0 (4)	C1—C6—S1—O2	−30.7 (2)
C7—C8—C13—C12	−178.3 (2)	C5—C6—S1—N1	−101.3 (2)
N2—C7—C14—C15	4.5 (3)	C1—C6—S1—N1	78.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.88 (2)	2.19 (2)	3.024 (3)	160 (2)
C1—H1···Cl1ii	0.93	2.91	3.694 (3)	143
C10—H10···Cl1′iii	0.93	2.76	3.476 (7)	134
C16—H16···O1iv	0.93	2.54	3.339 (3)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO2i	0.88(2)	2.19(2)	3.024(3)	160(2)
C10H10Cl1ii	0.93	2.76	3.476(7)	134
C16H16O1iii	0.93	2.54	3.339(3)	145

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