(E)-2-(2,3-Dimethyl-anilino)-N'-(thio-phen-2-yl-methyl-idene)benzohydrazide.

In the title compound, C(20)H(19)N(3)OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thio-phene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thio-phene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thio-phene ring and the benzene ring are twisted from the mean plane of the C(=O)-N-N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C-H⋯π inter-actions.

Related literature

For background to the chemistry and biological activity of diaryl amines, see: Reddy et al. (2010 ▶). For related structures, see: Bhat et al. (2012a ▶,b ▶,c ▶); Wang et al. (2010 ▶); Tian et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H19N3OS

M = 349.44

Monoclinic,

a = 14.0922 (14) Å

b = 15.9682 (15) Å

c = 8.1338 (8) Å

β = 105.344 (2)°

V = 1765.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.34 × 0.07 × 0.04 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.936, T max = 0.992

14626 measured reflections

5082 independent reflections

3338 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.128

S = 1.01

5082 reflections

236 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203259X/hb6898sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203259X/hb6898Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203259X/hb6898Isup3.cml

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

C20H19N3OS	F(000) = 736
Mr = 349.44	Dx = 1.315 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1664 reflections
a = 14.0922 (14) Å	θ = 2.9–24.3°
b = 15.9682 (15) Å	µ = 0.20 mm−1
c = 8.1338 (8) Å	T = 100 K
β = 105.344 (2)°	Needle, yellow
V = 1765.1 (3) Å3	0.34 × 0.07 × 0.04 mm
Z = 4

Bruker APEX DUO CCD diffractometer	5082 independent reflections
Radiation source: fine-focus sealed tube	3338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→19
Tmin = 0.936, Tmax = 0.992	k = −18→22
14626 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3
5082 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.10235 (4)	0.29345 (3)	0.79119 (6)	0.02004 (13)
O1	0.44269 (10)	0.16844 (8)	0.95045 (15)	0.0164 (3)
N1	0.63024 (13)	0.11358 (11)	1.0630 (2)	0.0221 (4)
N2	0.38625 (12)	0.23505 (10)	1.1518 (2)	0.0152 (3)
N3	0.30320 (11)	0.26223 (9)	1.03158 (19)	0.0152 (3)
C1	0.72104 (15)	−0.01298 (12)	1.0366 (2)	0.0219 (4)
H1A	0.6781	−0.0443	1.0854	0.026*
C2	0.79626 (16)	−0.05289 (12)	0.9882 (3)	0.0225 (4)
H2A	0.8060	−0.1114	1.0056	0.027*
C3	0.85748 (15)	−0.00697 (12)	0.9138 (2)	0.0209 (4)
H3A	0.9097	−0.0344	0.8817	0.025*
C4	0.84361 (14)	0.07824 (12)	0.8855 (2)	0.0173 (4)
C5	0.76785 (14)	0.12003 (11)	0.9365 (2)	0.0164 (4)
C6	0.70796 (14)	0.07299 (12)	1.0141 (2)	0.0171 (4)
C7	0.60869 (14)	0.10490 (11)	1.2183 (2)	0.0170 (4)
C8	0.67460 (15)	0.06586 (12)	1.3575 (2)	0.0203 (4)
H8A	0.7349	0.0443	1.3442	0.024*
C9	0.65339 (16)	0.05829 (12)	1.5130 (3)	0.0239 (4)
H9A	0.6989	0.0310	1.6044	0.029*
C10	0.56674 (16)	0.08987 (12)	1.5376 (2)	0.0233 (4)
H10A	0.5523	0.0841	1.6447	0.028*
C11	0.50153 (15)	0.13000 (11)	1.4038 (2)	0.0188 (4)
H11A	0.4420	0.1519	1.4203	0.023*
C12	0.52102 (14)	0.13927 (11)	1.2440 (2)	0.0150 (4)
C13	0.44837 (13)	0.18131 (11)	1.1041 (2)	0.0142 (4)
C14	0.25109 (14)	0.31569 (11)	1.0879 (2)	0.0163 (4)
H14A	0.2759	0.3391	1.1983	0.020*
C15	0.15535 (14)	0.34032 (11)	0.9847 (2)	0.0156 (4)
C16	0.09047 (15)	0.39305 (12)	1.0313 (3)	0.0207 (4)
H16A	0.1061	0.4246	1.1340	0.025*
C17	−0.00236 (15)	0.39559 (13)	0.9101 (3)	0.0234 (4)
H17A	−0.0560	0.4289	0.9222	0.028*
C18	−0.00604 (15)	0.34505 (12)	0.7747 (3)	0.0227 (4)
H18A	−0.0625	0.3390	0.6811	0.027*
C19	0.90953 (17)	0.12491 (14)	0.7978 (3)	0.0294 (5)
H19A	0.9586	0.0863	0.7748	0.044*
H19B	0.9430	0.1704	0.8716	0.044*
H19C	0.8698	0.1483	0.6901	0.044*
C20	0.75020 (17)	0.21221 (12)	0.9033 (3)	0.0241 (4)
H20A	0.7177	0.2355	0.9857	0.036*
H20B	0.7081	0.2205	0.7875	0.036*
H20C	0.8133	0.2407	0.9149	0.036*
H1N2	0.3987 (16)	0.2551 (13)	1.257 (3)	0.024 (6)*
H1N1	0.5850 (19)	0.1361 (15)	0.985 (3)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0187 (3)	0.0212 (2)	0.0189 (2)	0.0013 (2)	0.00243 (18)	−0.00158 (19)
O1	0.0181 (7)	0.0193 (6)	0.0122 (6)	0.0016 (5)	0.0045 (5)	−0.0001 (5)
N1	0.0172 (9)	0.0300 (9)	0.0203 (9)	0.0093 (7)	0.0073 (7)	0.0073 (7)
N2	0.0136 (8)	0.0194 (8)	0.0116 (7)	0.0030 (6)	0.0013 (6)	−0.0016 (6)
N3	0.0127 (8)	0.0180 (7)	0.0134 (7)	0.0012 (6)	0.0008 (6)	0.0013 (6)
C1	0.0206 (10)	0.0214 (10)	0.0231 (10)	−0.0019 (8)	0.0047 (8)	0.0026 (8)
C2	0.0260 (11)	0.0164 (9)	0.0239 (10)	0.0038 (8)	0.0046 (9)	0.0002 (8)
C3	0.0191 (10)	0.0230 (10)	0.0201 (10)	0.0064 (8)	0.0044 (8)	−0.0023 (8)
C4	0.0163 (10)	0.0212 (9)	0.0141 (9)	−0.0002 (7)	0.0036 (7)	−0.0004 (7)
C5	0.0172 (10)	0.0169 (9)	0.0128 (9)	0.0003 (7)	−0.0001 (7)	−0.0004 (7)
C6	0.0136 (9)	0.0208 (9)	0.0163 (9)	0.0013 (7)	0.0029 (7)	−0.0004 (7)
C7	0.0164 (9)	0.0165 (9)	0.0174 (9)	0.0001 (7)	0.0036 (7)	−0.0006 (7)
C8	0.0159 (10)	0.0215 (9)	0.0203 (10)	0.0031 (8)	−0.0012 (8)	0.0011 (8)
C9	0.0267 (11)	0.0222 (10)	0.0171 (10)	0.0029 (9)	−0.0042 (8)	0.0003 (8)
C10	0.0319 (12)	0.0239 (10)	0.0126 (9)	0.0030 (9)	0.0030 (8)	0.0005 (8)
C11	0.0201 (10)	0.0188 (9)	0.0174 (9)	0.0025 (8)	0.0050 (8)	−0.0007 (7)
C12	0.0142 (9)	0.0157 (8)	0.0143 (9)	−0.0016 (7)	0.0025 (7)	−0.0005 (7)
C13	0.0127 (9)	0.0142 (8)	0.0160 (9)	−0.0022 (7)	0.0042 (7)	−0.0002 (7)
C14	0.0171 (10)	0.0170 (9)	0.0141 (9)	−0.0004 (7)	0.0029 (7)	−0.0003 (7)
C15	0.0151 (9)	0.0169 (9)	0.0155 (9)	0.0003 (7)	0.0053 (7)	0.0029 (7)
C16	0.0209 (10)	0.0226 (10)	0.0195 (10)	0.0042 (8)	0.0068 (8)	−0.0013 (8)
C17	0.0177 (10)	0.0257 (10)	0.0280 (11)	0.0076 (8)	0.0083 (8)	0.0073 (9)
C18	0.0151 (10)	0.0250 (10)	0.0253 (11)	−0.0001 (8)	0.0009 (8)	0.0060 (8)
C19	0.0262 (12)	0.0360 (12)	0.0306 (12)	0.0019 (10)	0.0156 (10)	0.0064 (9)
C20	0.0335 (12)	0.0182 (9)	0.0225 (10)	0.0016 (9)	0.0107 (9)	0.0003 (8)

S1—C18	1.709 (2)	C8—C9	1.380 (3)
S1—C15	1.7243 (19)	C8—H8A	0.9500
O1—C13	1.248 (2)	C9—C10	1.384 (3)
N1—C7	1.382 (2)	C9—H9A	0.9500
N1—C6	1.417 (2)	C10—C11	1.382 (3)
N1—H1N1	0.85 (3)	C10—H10A	0.9500
N2—C13	1.354 (2)	C11—C12	1.406 (3)
N2—N3	1.382 (2)	C11—H11A	0.9500
N2—H1N2	0.89 (2)	C12—C13	1.475 (3)
N3—C14	1.287 (2)	C14—C15	1.442 (3)
C1—C2	1.381 (3)	C14—H14A	0.9500
C1—C6	1.391 (3)	C15—C16	1.368 (3)
C1—H1A	0.9500	C16—C17	1.415 (3)
C2—C3	1.387 (3)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.355 (3)
C3—C4	1.385 (3)	C17—H17A	0.9500
C3—H3A	0.9500	C18—H18A	0.9500
C4—C5	1.411 (3)	C19—H19A	0.9800
C4—C19	1.510 (3)	C19—H19B	0.9800
C5—C6	1.399 (3)	C19—H19C	0.9800
C5—C20	1.505 (3)	C20—H20A	0.9800
C7—C8	1.406 (3)	C20—H20B	0.9800
C7—C12	1.417 (3)	C20—H20C	0.9800
C18—S1—C15	91.42 (10)	C9—C10—H10A	120.5
C7—N1—C6	125.71 (17)	C10—C11—C12	121.68 (18)
C7—N1—H1N1	115.0 (17)	C10—C11—H11A	119.2
C6—N1—H1N1	117.7 (16)	C12—C11—H11A	119.2
C13—N2—N3	119.15 (15)	C11—C12—C7	119.14 (17)
C13—N2—H1N2	121.9 (15)	C11—C12—C13	119.70 (17)
N3—N2—H1N2	118.9 (15)	C7—C12—C13	121.12 (16)
C14—N3—N2	114.37 (15)	O1—C13—N2	121.08 (17)
C2—C1—C6	120.20 (18)	O1—C13—C12	123.01 (16)
C2—C1—H1A	119.9	N2—C13—C12	115.90 (15)
C6—C1—H1A	119.9	N3—C14—C15	120.51 (17)
C1—C2—C3	119.58 (18)	N3—C14—H14A	119.7
C1—C2—H2A	120.2	C15—C14—H14A	119.7
C3—C2—H2A	120.2	C16—C15—C14	126.67 (17)
C4—C3—C2	120.99 (19)	C16—C15—S1	111.12 (15)
C4—C3—H3A	119.5	C14—C15—S1	121.70 (14)
C2—C3—H3A	119.5	C15—C16—C17	112.75 (18)
C3—C4—C5	120.02 (17)	C15—C16—H16A	123.6
C3—C4—C19	119.07 (18)	C17—C16—H16A	123.6
C5—C4—C19	120.90 (17)	C18—C17—C16	112.26 (18)
C6—C5—C4	118.19 (17)	C18—C17—H17A	123.9
C6—C5—C20	121.03 (17)	C16—C17—H17A	123.9
C4—C5—C20	120.76 (17)	C17—C18—S1	112.46 (16)
C1—C6—C5	120.97 (18)	C17—C18—H18A	123.8
C1—C6—N1	119.99 (17)	S1—C18—H18A	123.8
C5—C6—N1	118.97 (17)	C4—C19—H19A	109.5
N1—C7—C8	121.51 (18)	C4—C19—H19B	109.5
N1—C7—C12	120.46 (17)	H19A—C19—H19B	109.5
C8—C7—C12	117.96 (17)	C4—C19—H19C	109.5
C9—C8—C7	121.33 (19)	H19A—C19—H19C	109.5
C9—C8—H8A	119.3	H19B—C19—H19C	109.5
C7—C8—H8A	119.3	C5—C20—H20A	109.5
C8—C9—C10	120.95 (18)	C5—C20—H20B	109.5
C8—C9—H9A	119.5	H20A—C20—H20B	109.5
C10—C9—H9A	119.5	C5—C20—H20C	109.5
C11—C10—C9	118.90 (18)	H20A—C20—H20C	109.5
C11—C10—H10A	120.5	H20B—C20—H20C	109.5
C13—N2—N3—C14	−177.33 (16)	C9—C10—C11—C12	0.1 (3)
C6—C1—C2—C3	−1.3 (3)	C10—C11—C12—C7	1.5 (3)
C1—C2—C3—C4	−0.7 (3)	C10—C11—C12—C13	178.95 (17)
C2—C3—C4—C5	1.6 (3)	N1—C7—C12—C11	−179.49 (18)
C2—C3—C4—C19	−177.56 (18)	C8—C7—C12—C11	−2.7 (3)
C3—C4—C5—C6	−0.4 (3)	N1—C7—C12—C13	3.1 (3)
C19—C4—C5—C6	178.70 (18)	C8—C7—C12—C13	179.91 (17)
C3—C4—C5—C20	−178.59 (18)	N3—N2—C13—O1	13.8 (3)
C19—C4—C5—C20	0.6 (3)	N3—N2—C13—C12	−165.63 (15)
C2—C1—C6—C5	2.5 (3)	C11—C12—C13—O1	−155.40 (18)
C2—C1—C6—N1	179.59 (18)	C7—C12—C13—O1	22.0 (3)
C4—C5—C6—C1	−1.6 (3)	C11—C12—C13—N2	24.0 (2)
C20—C5—C6—C1	176.56 (18)	C7—C12—C13—N2	−158.62 (17)
C4—C5—C6—N1	−178.73 (17)	N2—N3—C14—C15	−170.89 (16)
C20—C5—C6—N1	−0.6 (3)	N3—C14—C15—C16	176.61 (19)
C7—N1—C6—C1	49.4 (3)	N3—C14—C15—S1	5.5 (3)
C7—N1—C6—C5	−133.4 (2)	C18—S1—C15—C16	0.06 (15)
C6—N1—C7—C8	12.2 (3)	C18—S1—C15—C14	172.39 (16)
C6—N1—C7—C12	−171.05 (18)	C14—C15—C16—C17	−171.90 (18)
N1—C7—C8—C9	179.14 (19)	S1—C15—C16—C17	0.0 (2)
C12—C7—C8—C9	2.4 (3)	C15—C16—C17—C18	0.0 (3)
C7—C8—C9—C10	−0.8 (3)	C16—C17—C18—S1	0.1 (2)
C8—C9—C10—C11	−0.5 (3)	C15—S1—C18—C17	−0.07 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.89 (2)	1.96 (2)	2.808 (2)	160 (2)
N1—H1N1···O1	0.85 (2)	2.02 (3)	2.704 (2)	137 (2)
C1—H1A···O1ii	0.95	2.58	3.410 (2)	146
C3—H3A···Cg1iii	0.95	2.98	3.732 (2)	137
C9—H9A···Cg2iv	0.95	2.84	3.649 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C15–C18 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.89 (2)	1.96 (2)	2.808 (2)	160 (2)
N1—H1N1⋯O1	0.85 (2)	2.02 (3)	2.704 (2)	137 (2)
C1—H1A⋯O1ii	0.95	2.58	3.410 (2)	146
C3—H3A⋯Cg1iii	0.95	2.98	3.732 (2)	137
C9—H9A⋯Cg2iv	0.95	2.84	3.649 (2)	144

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