6-Methyl-N-(4-methoxy-phen-yl)-2-[(E)-(4-methyl-phen-yl)methyl-eneamino]-4,5,6,7-tetra-hydro-thieno[2,3-c]pyridine-3-carboxamide.

The molecular structure of the title compound, C(24)H(25)N(3)O(2)S, is stabilized by intra-molecular N-H⋯N, C-H⋯O and C-H⋯S hydrogen bonds. There are no significant inter-molecular inter-actions.

Related literature

For related literature, see: Gewald et al. (1966 ▶); Cohen et al. (1977 ▶); Csaszar & Morvay (1983 ▶); Lakshmi et al. (1985 ▶); Mohan & Saravanan (2003 ▶); Dzhurayev et al. (1992 ▶); Sebnis et al. (1999 ▶); Anilkumar et al. (2005 ▶); El-Maghraby, Haroun & Mohamed (1984 ▶).

Experimental

Crystal data

C24H25N3O2S

M = 419.53

Triclinic,

a = 8.3905 (11) Å

b = 9.9883 (13) Å

c = 12.9549 (17) Å

α = 91.375 (2)°

β = 94.789 (3)°

γ = 96.121 (2)°

V = 1075.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 292 (2) K

0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.967

10653 measured reflections

3967 independent reflections

2633 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.183

S = 1.14

3967 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017236/hg2409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017236/hg2409Isup2.hkl

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

C24H25N3O2S	Z = 2
Mr = 419.53	F000 = 444
Triclinic, P1	Dx = 1.296 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3905 (11) Å	Cell parameters from 380 reflections
b = 9.9883 (13) Å	θ = 1.6–28.6º
c = 12.9549 (17) Å	µ = 0.18 mm−1
α = 91.375 (2)º	T = 292 (2) K
β = 94.789 (3)º	Block, yellow
γ = 96.121 (2)º	0.32 × 0.28 × 0.22 mm
V = 1075.2 (2) Å3

Bruker SMART CCD area-detector diffractometer	3967 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 291(2) K	θmax = 25.5º
ψ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.942, Tmax = 0.967	k = −12→12
10653 measured reflections	l = −15→15

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)] = 0.085	H-atom parameters constrained
wR(F2) = 0.184	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.1278P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
3967 reflections	Δρmax = 0.26 e Å−3
274 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.15650 (12)	0.11892 (10)	0.10349 (7)	0.0563 (3)
O1	0.5787 (3)	0.2412 (3)	0.3856 (2)	0.0713 (9)
O2	0.9097 (3)	0.8527 (2)	0.5084 (2)	0.0604 (7)
N1	0.3079 (3)	0.3800 (3)	0.1240 (2)	0.0471 (7)
N2	0.5036 (4)	0.4298 (3)	0.3103 (2)	0.0523 (8)
H2	0.4367	0.4575	0.2637	0.063*
N3	0.2336 (4)	−0.2086 (3)	0.2703 (2)	0.0522 (8)
C1	0.2503 (5)	0.4032 (4)	0.0322 (3)	0.0551 (10)
H1	0.1949	0.3317	−0.0078	0.066*
C2	0.2865 (4)	0.2518 (3)	0.1637 (3)	0.0442 (9)
C3	0.3661 (4)	0.2116 (3)	0.2540 (3)	0.0433 (9)
C4	0.3748 (5)	−0.0062 (4)	0.3650 (3)	0.0516 (10)
H4A	0.4844	−0.0254	0.3582	0.062*
H4B	0.3741	0.0474	0.4283	0.062*
C5	0.2676 (5)	−0.1373 (4)	0.3715 (3)	0.0568 (10)
H5A	0.3195	−0.1948	0.4200	0.068*
H5B	0.1670	−0.1185	0.3976	0.068*
C6	0.1331 (5)	−0.1315 (4)	0.2017 (3)	0.0556 (10)
H6A	0.0266	−0.1339	0.2259	0.067*
H6B	0.1224	−0.1715	0.1321	0.067*
C7	0.2076 (4)	0.0119 (4)	0.1999 (3)	0.0469 (9)
C8	0.3183 (4)	0.0725 (3)	0.2738 (3)	0.0415 (8)
C9	0.4911 (4)	0.2950 (4)	0.3227 (3)	0.0479 (9)
C10	0.1536 (5)	−0.3431 (4)	0.2811 (3)	0.0664 (12)
H10A	0.0545	−0.3371	0.3121	0.100*
H10B	0.2219	−0.3938	0.3244	0.100*
H10C	0.1315	−0.3874	0.2141	0.100*
C11	0.6118 (4)	0.5304 (3)	0.3637 (3)	0.0460 (9)
C12	0.6143 (5)	0.6609 (4)	0.3305 (3)	0.0596 (11)
H12	0.5460	0.6787	0.2734	0.072*
C13	0.7141 (5)	0.7643 (4)	0.3789 (3)	0.0603 (11)
H13	0.7138	0.8508	0.3538	0.072*
C14	0.8163 (4)	0.7420 (4)	0.4655 (3)	0.0466 (9)
C15	0.8154 (5)	0.6133 (4)	0.4991 (3)	0.0573 (10)
H15	0.8838	0.5961	0.5563	0.069*
C16	0.7151 (5)	0.5082 (4)	0.4498 (3)	0.0591 (11)
H16	0.7166	0.4216	0.4745	0.071*
C17	0.2670 (4)	0.5351 (4)	−0.0126 (3)	0.0493 (9)
C18	0.1988 (6)	0.5521 (4)	−0.1128 (3)	0.0772 (14)
H18	0.1445	0.4782	−0.1505	0.093*
C19	0.2106 (6)	0.6756 (5)	−0.1563 (3)	0.0775 (14)
H19	0.1640	0.6838	−0.2233	0.093*
C20	0.2889 (4)	0.7875 (4)	−0.1044 (3)	0.0535 (10)
C21	0.3603 (5)	0.7708 (4)	−0.0057 (3)	0.0634 (11)
H21	0.4165	0.8445	0.0312	0.076*
C22	0.3487 (5)	0.6468 (4)	0.0379 (3)	0.0625 (11)
H22	0.3982	0.6384	0.1040	0.075*
C23	1.0176 (5)	0.8341 (4)	0.5968 (3)	0.0619 (11)
H23A	0.9580	0.7953	0.6508	0.093*
H23B	1.0731	0.9197	0.6208	0.093*
H23C	1.0944	0.7750	0.5781	0.093*
C24	0.2999 (5)	0.9248 (4)	−0.1523 (3)	0.0717 (12)
H24A	0.2827	0.9139	−0.2264	0.108*
H24B	0.4045	0.9718	−0.1337	0.108*
H24C	0.2193	0.9756	−0.1273	0.108*

	U11	U22	U33	U12	U13	U23
S1	0.0607 (7)	0.0545 (6)	0.0497 (6)	0.0002 (5)	−0.0136 (5)	0.0075 (5)
O1	0.0739 (19)	0.0560 (17)	0.0772 (19)	0.0045 (14)	−0.0340 (16)	0.0122 (14)
O2	0.0565 (17)	0.0483 (16)	0.0715 (18)	−0.0001 (13)	−0.0165 (14)	0.0049 (13)
N1	0.0499 (18)	0.0470 (18)	0.0431 (17)	0.0026 (14)	−0.0026 (14)	0.0093 (14)
N2	0.057 (2)	0.0468 (19)	0.0492 (18)	0.0056 (15)	−0.0159 (15)	0.0039 (14)
N3	0.056 (2)	0.0458 (18)	0.0542 (19)	0.0054 (15)	−0.0008 (15)	0.0083 (15)
C1	0.063 (3)	0.053 (2)	0.045 (2)	0.0000 (19)	−0.0124 (19)	0.0076 (18)
C2	0.045 (2)	0.047 (2)	0.040 (2)	0.0038 (17)	−0.0019 (16)	0.0018 (16)
C3	0.040 (2)	0.049 (2)	0.041 (2)	0.0107 (17)	−0.0005 (16)	0.0045 (16)
C4	0.058 (2)	0.054 (2)	0.044 (2)	0.0104 (19)	0.0002 (18)	0.0074 (17)
C5	0.071 (3)	0.051 (2)	0.048 (2)	0.006 (2)	0.005 (2)	0.0053 (18)
C6	0.053 (2)	0.053 (2)	0.059 (2)	0.0027 (19)	−0.0004 (19)	0.0033 (19)
C7	0.047 (2)	0.052 (2)	0.044 (2)	0.0109 (18)	0.0027 (17)	0.0064 (17)
C8	0.041 (2)	0.044 (2)	0.0399 (19)	0.0080 (16)	0.0003 (16)	0.0031 (15)
C9	0.049 (2)	0.049 (2)	0.044 (2)	0.0047 (18)	−0.0066 (17)	0.0058 (17)
C10	0.073 (3)	0.052 (3)	0.073 (3)	−0.001 (2)	0.004 (2)	0.007 (2)
C11	0.047 (2)	0.043 (2)	0.047 (2)	0.0043 (17)	−0.0055 (17)	0.0004 (17)
C12	0.062 (3)	0.050 (2)	0.062 (2)	0.004 (2)	−0.023 (2)	0.0092 (19)
C13	0.060 (3)	0.044 (2)	0.074 (3)	0.0064 (19)	−0.015 (2)	0.017 (2)
C14	0.046 (2)	0.041 (2)	0.052 (2)	0.0048 (17)	0.0009 (18)	0.0040 (17)
C15	0.068 (3)	0.049 (2)	0.051 (2)	0.003 (2)	−0.018 (2)	0.0069 (18)
C16	0.074 (3)	0.047 (2)	0.053 (2)	0.005 (2)	−0.018 (2)	0.0157 (18)
C17	0.050 (2)	0.056 (2)	0.040 (2)	0.0031 (19)	−0.0073 (17)	0.0060 (18)
C18	0.104 (4)	0.064 (3)	0.053 (3)	−0.011 (3)	−0.030 (2)	0.012 (2)
C19	0.096 (4)	0.073 (3)	0.056 (3)	−0.002 (3)	−0.028 (2)	0.016 (2)
C20	0.049 (2)	0.061 (3)	0.053 (2)	0.012 (2)	0.0074 (19)	0.014 (2)
C21	0.071 (3)	0.055 (3)	0.059 (3)	−0.008 (2)	−0.006 (2)	0.002 (2)
C22	0.074 (3)	0.067 (3)	0.043 (2)	0.002 (2)	−0.011 (2)	0.012 (2)
C23	0.060 (3)	0.066 (3)	0.054 (2)	0.001 (2)	−0.015 (2)	−0.001 (2)
C24	0.076 (3)	0.068 (3)	0.072 (3)	0.010 (2)	0.009 (2)	0.018 (2)

S1—C7	1.721 (3)	C10—H10B	0.9600
S1—C2	1.749 (4)	C10—H10C	0.9600
O1—C9	1.225 (4)	C11—C12	1.380 (5)
O2—C14	1.363 (4)	C11—C16	1.392 (5)
O2—C23	1.427 (4)	C12—C13	1.363 (5)
N1—C1	1.282 (4)	C12—H12	0.9300
N1—C2	1.391 (4)	C13—C14	1.391 (5)
N2—C9	1.354 (4)	C13—H13	0.9300
N2—C11	1.407 (4)	C14—C15	1.366 (5)
N2—H2	0.8600	C15—C16	1.381 (5)
N3—C10	1.452 (4)	C15—H15	0.9300
N3—C6	1.463 (4)	C16—H16	0.9300
N3—C5	1.469 (5)	C17—C22	1.367 (5)
C1—C17	1.450 (5)	C17—C18	1.397 (5)
C1—H1	0.9300	C18—C19	1.366 (5)
C2—C3	1.387 (4)	C18—H18	0.9300
C3—C8	1.440 (5)	C19—C20	1.366 (6)
C3—C9	1.485 (5)	C19—H19	0.9300
C4—C5	1.516 (5)	C20—C21	1.387 (5)
C4—C8	1.506 (4)	C20—C24	1.516 (5)
C4—H4A	0.9700	C21—C22	1.371 (5)
C4—H4B	0.9700	C21—H21	0.9300
C5—H5A	0.9700	C22—H22	0.9300
C5—H5B	0.9700	C23—H23A	0.9600
C6—C7	1.502 (5)	C23—H23B	0.9600
C6—H6A	0.9700	C23—H23C	0.9600
C6—H6B	0.9700	C24—H24A	0.9600
C7—C8	1.360 (5)	C24—H24B	0.9600
C10—H10A	0.9600	C24—H24C	0.9600
C7—S1—C2	91.41 (17)	H10B—C10—H10C	109.5
C14—O2—C23	117.7 (3)	C12—C11—C16	117.2 (3)
C1—N1—C2	121.1 (3)	C12—C11—N2	118.4 (3)
C9—N2—C11	128.4 (3)	C16—C11—N2	124.4 (3)
C9—N2—H2	115.8	C13—C12—C11	121.9 (3)
C11—N2—H2	115.8	C13—C12—H12	119.0
C10—N3—C6	110.1 (3)	C11—C12—H12	119.0
C10—N3—C5	110.9 (3)	C12—C13—C14	120.7 (3)
C6—N3—C5	109.3 (3)	C12—C13—H13	119.6
N1—C1—C17	123.4 (3)	C14—C13—H13	119.6
N1—C1—H1	118.3	O2—C14—C15	126.2 (3)
C17—C1—H1	118.3	O2—C14—C13	115.9 (3)
C3—C2—N1	125.1 (3)	C15—C14—C13	117.9 (3)
C3—C2—S1	111.3 (3)	C14—C15—C16	121.4 (3)
N1—C2—S1	123.6 (2)	C14—C15—H15	119.3
C2—C3—C8	111.7 (3)	C16—C15—H15	119.3
C2—C3—C9	126.5 (3)	C15—C16—C11	120.7 (3)
C8—C3—C9	121.8 (3)	C15—C16—H16	119.6
C5—C4—C8	111.0 (3)	C11—C16—H16	119.6
C5—C4—H4A	109.4	C22—C17—C18	116.7 (3)
C8—C4—H4A	109.4	C22—C17—C1	123.5 (3)
C5—C4—H4B	109.4	C18—C17—C1	119.7 (3)
C8—C4—H4B	109.4	C19—C18—C17	121.0 (4)
H4A—C4—H4B	108.0	C19—C18—H18	119.5
N3—C5—C4	112.0 (3)	C17—C18—H18	119.5
N3—C5—H5A	109.2	C18—C19—C20	121.9 (4)
C4—C5—H5A	109.2	C18—C19—H19	119.0
N3—C5—H5B	109.2	C20—C19—H19	119.0
C4—C5—H5B	109.2	C19—C20—C21	117.4 (4)
H5A—C5—H5B	107.9	C19—C20—C24	121.8 (4)
N3—C6—C7	109.9 (3)	C21—C20—C24	120.8 (4)
N3—C6—H6A	109.7	C22—C21—C20	120.7 (4)
C7—C6—H6A	109.7	C22—C21—H21	119.7
N3—C6—H6B	109.7	C20—C21—H21	119.7
C7—C6—H6B	109.7	C21—C22—C17	122.2 (3)
H6A—C6—H6B	108.2	C21—C22—H22	118.9
C8—C7—C6	124.7 (3)	C17—C22—H22	118.9
C8—C7—S1	112.6 (3)	O2—C23—H23A	109.5
C6—C7—S1	122.6 (3)	O2—C23—H23B	109.5
C7—C8—C3	113.0 (3)	H23A—C23—H23B	109.5
C7—C8—C4	119.7 (3)	O2—C23—H23C	109.5
C3—C8—C4	127.4 (3)	H23A—C23—H23C	109.5
O1—C9—N2	123.0 (3)	H23B—C23—H23C	109.5
O1—C9—C3	120.2 (3)	C20—C24—H24A	109.5
N2—C9—C3	116.9 (3)	C20—C24—H24B	109.5
N3—C10—H10A	109.5	H24A—C24—H24B	109.5
N3—C10—H10B	109.5	C20—C24—H24C	109.5
H10A—C10—H10B	109.5	H24A—C24—H24C	109.5
N3—C10—H10C	109.5	H24B—C24—H24C	109.5
H10A—C10—H10C	109.5
C2—N1—C1—C17	179.1 (3)	C2—C3—C9—O1	−162.9 (4)
C1—N1—C2—C3	168.5 (4)	C8—C3—C9—O1	14.4 (5)
C1—N1—C2—S1	−10.3 (5)	C2—C3—C9—N2	16.0 (5)
C7—S1—C2—C3	0.7 (3)	C8—C3—C9—N2	−166.7 (3)
C7—S1—C2—N1	179.6 (3)	C9—N2—C11—C12	173.1 (4)
N1—C2—C3—C8	−179.6 (3)	C9—N2—C11—C16	−8.3 (6)
S1—C2—C3—C8	−0.7 (4)	C16—C11—C12—C13	0.4 (6)
N1—C2—C3—C9	−2.1 (6)	N2—C11—C12—C13	179.1 (4)
S1—C2—C3—C9	176.8 (3)	C11—C12—C13—C14	−1.0 (7)
C10—N3—C5—C4	170.6 (3)	C23—O2—C14—C15	0.0 (5)
C6—N3—C5—C4	−67.8 (4)	C23—O2—C14—C13	−179.4 (3)
C8—C4—C5—N3	45.9 (4)	C12—C13—C14—O2	−179.4 (4)
C10—N3—C6—C7	173.8 (3)	C12—C13—C14—C15	1.1 (6)
C5—N3—C6—C7	51.6 (4)	O2—C14—C15—C16	179.8 (4)
N3—C6—C7—C8	−20.0 (5)	C13—C14—C15—C16	−0.8 (6)
N3—C6—C7—S1	161.5 (3)	C14—C15—C16—C11	0.3 (7)
C2—S1—C7—C8	−0.5 (3)	C12—C11—C16—C15	−0.1 (6)
C2—S1—C7—C6	178.1 (3)	N2—C11—C16—C15	−178.7 (4)
C6—C7—C8—C3	−178.4 (3)	N1—C1—C17—C22	1.5 (6)
S1—C7—C8—C3	0.1 (4)	N1—C1—C17—C18	−179.2 (4)
C6—C7—C8—C4	0.5 (5)	C22—C17—C18—C19	−1.6 (7)
S1—C7—C8—C4	179.1 (3)	C1—C17—C18—C19	179.0 (4)
C2—C3—C8—C7	0.4 (4)	C17—C18—C19—C20	0.0 (8)
C9—C3—C8—C7	−177.3 (3)	C18—C19—C20—C21	1.5 (7)
C2—C3—C8—C4	−178.4 (3)	C18—C19—C20—C24	−179.1 (4)
C9—C3—C8—C4	3.9 (6)	C19—C20—C21—C22	−1.4 (6)
C5—C4—C8—C7	−12.8 (5)	C24—C20—C21—C22	179.3 (4)
C5—C4—C8—C3	165.9 (3)	C20—C21—C22—C17	−0.3 (7)
C11—N2—C9—O1	−0.3 (6)	C18—C17—C22—C21	1.8 (6)
C11—N2—C9—C3	−179.2 (3)	C1—C17—C22—C21	−178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.86	2.12	2.807 (4)	137
C1—H1···S1	0.93	2.60	3.051 (4)	110
C16—H16···O1	0.93	2.27	2.863 (5)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1	0.86	2.12	2.807 (4)	137
C1—H1⋯S1	0.93	2.60	3.051 (4)	110
C16—H16⋯O1	0.93	2.27	2.863 (5)	121