Ethyl 3-(4-methyl-benzene-sulfonamido)thieno[2,3-b]pyridine-2-carboxyl-ate.

The thieno[2,3-b]pyridine ring system of the title compound, C(17)H(16)N(2)O(4)S(2), is essentially planar, the amino and carbonyl groups being nearly coplanar with the heterocyclic ring system. There are two N-H⋯O hydrogen-bonding inter-actions involving the same N-H donor set and two different acceptors, one in an intra-molecular bond helping to fix the mol-ecular geometry and the other defining a dimeric structure around the symmetry centre at (0, , ).

Related literature

For general background, see: Litvinov et al. (2005 ▶).

Experimental

Crystal data

C17H16N2O4S2

M = 376.46

Orthorhombic,

a = 14.809 (4) Å

b = 11.892 (3) Å

c = 19.494 (5) Å

V = 3433.1 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 293 (2) K

0.46 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: spherical [modified Dwiggins (1975 ▶) interpolation procedure] T min = 0.861, T max = 0.872

3590 measured reflections

3075 independent reflections

2032 reflections with I > 2σ(I)

R int = 0.005

3 standard reflections every 200 reflections intensity decay: 3.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.186

S = 1.13

3075 reflections

233 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.74 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000269/bg2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000269/bg2232Isup2.hkl

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

C17H16N2O4S2	F(000) = 1568
Mr = 376.46	Dx = 1.457 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24 reflections
a = 14.809 (4) Å	θ = 4.5–7.7°
b = 11.892 (3) Å	µ = 0.34 mm−1
c = 19.494 (5) Å	T = 293 K
V = 3433.1 (15) Å3	Block, colourless
Z = 8	0.46 × 0.44 × 0.42 mm

Enraf–Nonius CAD-4 diffractometer	2032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.005
graphite	θmax = 25.6°, θmin = 2.1°
ω/2θ scans	h = −17→10
Absorption correction: for a sphere (interpolation; International Tables for X-ray Crystallography, 1959, Vol II, p. 302; 1992, Vol. C, p. 523); Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification.	k = −2→14
Tmin = 0.861, Tmax = 0.872	l = −13→23
3590 measured reflections	3 standard reflections every 200 reflections
3075 independent reflections	intensity decay: 3.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.0996P)2 + 1.4444P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3075 reflections	Δρmax = 0.36 e Å−3
233 parameters	Δρmin = −0.74 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0175 (17)

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	0.09964 (6)	0.61780 (8)	0.44511 (5)	0.0446 (3)
S2	−0.09888 (7)	0.97224 (9)	0.42142 (5)	0.0519 (3)
O1	0.14122 (18)	0.6604 (2)	0.38494 (13)	0.0557 (7)
O2	0.09322 (18)	0.4988 (2)	0.45432 (15)	0.0578 (8)
O3	−0.12382 (18)	0.9327 (2)	0.56425 (12)	0.0497 (7)
O4	−0.0664 (2)	0.7593 (3)	0.57213 (13)	0.0617 (8)
N1	−0.0053 (2)	0.6628 (3)	0.44558 (15)	0.0422 (7)
H1N	−0.033 (3)	0.642 (3)	0.4875 (12)	0.067 (13)*
N2	−0.0759 (3)	0.9677 (3)	0.28514 (19)	0.0651 (10)
C1	0.2655 (4)	0.8311 (6)	0.6960 (4)	0.129 (3)
H1A	0.2173	0.8723	0.7172	0.194*
H1B	0.3126	0.8821	0.6828	0.194*
H1C	0.2890	0.7769	0.7278	0.194*
C2	0.2296 (3)	0.7703 (6)	0.6323 (3)	0.0842 (18)
C3	0.2462 (3)	0.8165 (5)	0.5677 (3)	0.0783 (15)
H3	0.2827	0.8798	0.5635	0.094*
C4	0.2083 (3)	0.7678 (3)	0.5100 (2)	0.0578 (11)
H4	0.2197	0.7975	0.4668	0.069*
C5	0.1529 (2)	0.6741 (3)	0.51725 (19)	0.0469 (9)
C6	0.1372 (3)	0.6279 (4)	0.5808 (2)	0.0622 (11)
H6	0.1006	0.5646	0.5850	0.075*
C7	0.1755 (3)	0.6751 (5)	0.6376 (2)	0.0826 (16)
H7	0.1652	0.6433	0.6805	0.099*
C8	−0.0288 (2)	0.7731 (3)	0.42354 (17)	0.0399 (8)
C9	−0.0649 (2)	0.8527 (3)	0.46538 (18)	0.0417 (8)
C10	−0.0648 (2)	0.9136 (4)	0.34493 (19)	0.0495 (10)
C11	−0.0285 (2)	0.8071 (3)	0.35295 (17)	0.0434 (9)
C12	−0.0836 (2)	0.8412 (4)	0.53894 (18)	0.0446 (9)
C13	−0.1472 (3)	0.9290 (3)	0.63719 (18)	0.0524 (10)
H13A	−0.0931	0.9208	0.6648	0.063*
H13B	−0.1867	0.8657	0.6464	0.063*
C14	−0.1939 (3)	1.0370 (4)	0.6541 (2)	0.0623 (11)
H14A	−0.1538	1.0988	0.6456	0.093*
H14B	−0.2112	1.0367	0.7016	0.093*
H14C	−0.2468	1.0446	0.6260	0.093*
C15	−0.0523 (3)	0.9075 (5)	0.2299 (2)	0.0724 (14)
H15	−0.0606	0.9403	0.1870	0.087*
C16	−0.0170 (3)	0.8024 (5)	0.2319 (2)	0.0662 (13)
H16	−0.0015	0.7670	0.1910	0.079*
C17	−0.0036 (2)	0.7466 (4)	0.29326 (19)	0.0511 (10)
H17	0.0202	0.6743	0.2952	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0471 (6)	0.0449 (6)	0.0417 (6)	0.0037 (4)	0.0058 (4)	−0.0009 (4)
S2	0.0528 (6)	0.0546 (7)	0.0483 (6)	0.0089 (5)	−0.0010 (4)	0.0069 (5)
O1	0.0528 (15)	0.0707 (19)	0.0435 (16)	0.0033 (14)	0.0104 (12)	0.0073 (13)
O2	0.0690 (19)	0.0428 (17)	0.0617 (19)	0.0040 (13)	0.0060 (13)	−0.0015 (13)
O3	0.0542 (15)	0.0584 (17)	0.0365 (14)	0.0043 (13)	0.0087 (11)	−0.0027 (12)
O4	0.084 (2)	0.066 (2)	0.0350 (15)	0.0072 (16)	0.0038 (14)	0.0072 (14)
N1	0.0420 (16)	0.0428 (17)	0.0418 (17)	−0.0035 (13)	0.0015 (13)	0.0029 (13)
N2	0.072 (2)	0.075 (3)	0.048 (2)	0.0039 (19)	−0.0066 (17)	0.0199 (19)
C1	0.093 (4)	0.175 (7)	0.120 (5)	0.051 (4)	−0.052 (4)	−0.086 (5)
C2	0.047 (3)	0.123 (5)	0.083 (4)	0.031 (3)	−0.024 (2)	−0.047 (3)
C3	0.053 (3)	0.084 (4)	0.098 (4)	0.010 (2)	−0.017 (3)	−0.028 (3)
C4	0.050 (2)	0.049 (2)	0.074 (3)	0.0013 (18)	−0.005 (2)	−0.002 (2)
C5	0.043 (2)	0.050 (2)	0.048 (2)	0.0082 (17)	0.0021 (16)	0.0002 (17)
C6	0.053 (2)	0.079 (3)	0.055 (3)	−0.001 (2)	−0.0040 (19)	0.007 (2)
C7	0.058 (3)	0.140 (5)	0.050 (3)	0.026 (3)	−0.010 (2)	−0.012 (3)
C8	0.0349 (17)	0.053 (2)	0.0318 (18)	−0.0077 (15)	−0.0022 (14)	0.0041 (15)
C9	0.0363 (17)	0.055 (2)	0.0337 (18)	0.0026 (16)	−0.0032 (14)	0.0031 (16)
C10	0.0427 (19)	0.065 (3)	0.041 (2)	−0.0023 (18)	−0.0064 (16)	0.0121 (18)
C11	0.0354 (17)	0.063 (2)	0.0315 (19)	−0.0086 (16)	−0.0014 (14)	0.0019 (17)
C12	0.0399 (19)	0.063 (2)	0.0313 (19)	−0.0064 (17)	−0.0003 (14)	0.0004 (18)
C13	0.059 (2)	0.063 (3)	0.034 (2)	−0.003 (2)	0.0059 (17)	−0.0042 (18)
C14	0.068 (3)	0.068 (3)	0.051 (3)	−0.007 (2)	0.012 (2)	−0.011 (2)
C15	0.071 (3)	0.106 (4)	0.040 (3)	−0.005 (3)	−0.009 (2)	0.023 (3)
C16	0.060 (3)	0.108 (4)	0.030 (2)	−0.024 (3)	−0.0005 (17)	0.003 (2)
C17	0.050 (2)	0.061 (3)	0.042 (2)	−0.0113 (18)	0.0022 (16)	−0.0028 (17)

S1—O1	1.418 (3)	C4—H4	0.9300
S1—O2	1.430 (3)	C5—C6	1.375 (6)
S1—N1	1.643 (3)	C6—C7	1.366 (6)
S1—C5	1.746 (4)	C6—H6	0.9300
S2—C10	1.722 (4)	C7—H7	0.9300
S2—C9	1.734 (4)	C8—C9	1.359 (5)
O3—C12	1.335 (5)	C8—C11	1.434 (5)
O3—C13	1.464 (4)	C9—C12	1.467 (5)
O4—C12	1.197 (5)	C10—C11	1.384 (6)
N1—C8	1.423 (5)	C11—C17	1.417 (5)
N1—H1N	0.95 (3)	C13—C14	1.496 (6)
N2—C15	1.340 (6)	C13—H13A	0.9700
N2—C10	1.342 (5)	C13—H13B	0.9700
C1—C2	1.532 (7)	C14—H14A	0.9600
C1—H1A	0.9600	C14—H14B	0.9600
C1—H1B	0.9600	C14—H14C	0.9600
C1—H1C	0.9600	C15—C16	1.355 (7)
C2—C7	1.390 (8)	C15—H15	0.9300
C2—C3	1.395 (8)	C16—C17	1.383 (6)
C3—C4	1.385 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.390 (5)
O1—S1—O2	119.11 (18)	C9—C8—N1	123.8 (3)
O1—S1—N1	107.37 (16)	C9—C8—C11	112.4 (3)
O2—S1—N1	105.00 (16)	N1—C8—C11	123.3 (3)
O1—S1—C5	109.43 (18)	C8—C9—C12	126.6 (3)
O2—S1—C5	107.97 (18)	C8—C9—S2	112.9 (3)
N1—S1—C5	107.34 (16)	C12—C9—S2	120.3 (3)
C10—S2—C9	90.63 (18)	N2—C10—C11	125.8 (4)
C12—O3—C13	116.1 (3)	N2—C10—S2	121.5 (4)
C8—N1—S1	122.0 (2)	C11—C10—S2	112.7 (3)
C8—N1—H1N	114 (3)	C10—C11—C17	118.2 (3)
S1—N1—H1N	109 (3)	C10—C11—C8	111.4 (3)
C15—N2—C10	114.2 (4)	C17—C11—C8	130.2 (4)
C2—C1—H1A	109.5	O4—C12—O3	124.0 (3)
C2—C1—H1B	109.5	O4—C12—C9	124.4 (4)
H1A—C1—H1B	109.5	O3—C12—C9	111.7 (3)
C2—C1—H1C	109.5	O3—C13—C14	107.3 (3)
H1A—C1—H1C	109.5	O3—C13—H13A	110.3
H1B—C1—H1C	109.5	C14—C13—H13A	110.3
C7—C2—C3	119.4 (5)	O3—C13—H13B	110.3
C7—C2—C1	121.5 (7)	C14—C13—H13B	110.3
C3—C2—C1	118.9 (6)	H13A—C13—H13B	108.5
C4—C3—C2	119.7 (5)	C13—C14—H14A	109.5
C4—C3—H3	120.1	C13—C14—H14B	109.5
C2—C3—H3	120.1	H14A—C14—H14B	109.5
C3—C4—C5	119.5 (5)	C13—C14—H14C	109.5
C3—C4—H4	120.3	H14A—C14—H14C	109.5
C5—C4—H4	120.3	H14B—C14—H14C	109.5
C6—C5—C4	120.8 (4)	N2—C15—C16	124.8 (4)
C6—C5—S1	119.7 (3)	N2—C15—H15	117.6
C4—C5—S1	119.5 (3)	C16—C15—H15	117.6
C7—C6—C5	119.7 (5)	C15—C16—C17	121.6 (4)
C7—C6—H6	120.1	C15—C16—H16	119.2
C5—C6—H6	120.1	C17—C16—H16	119.2
C6—C7—C2	120.9 (5)	C16—C17—C11	115.4 (4)
C6—C7—H7	119.6	C16—C17—H17	122.3
C2—C7—H7	119.6	C11—C17—H17	122.3
O1—S1—N1—C8	−38.8 (3)	C10—S2—C9—C12	−174.1 (3)
O2—S1—N1—C8	−166.5 (3)	C15—N2—C10—C11	3.0 (6)
C5—S1—N1—C8	78.8 (3)	C15—N2—C10—S2	−175.2 (3)
C7—C2—C3—C4	0.5 (7)	C9—S2—C10—N2	178.1 (4)
C1—C2—C3—C4	−174.8 (4)	C9—S2—C10—C11	−0.3 (3)
C2—C3—C4—C5	0.9 (7)	N2—C10—C11—C17	−2.6 (6)
C3—C4—C5—C6	−1.5 (6)	S2—C10—C11—C17	175.8 (3)
C3—C4—C5—S1	176.2 (3)	N2—C10—C11—C8	−178.3 (4)
O1—S1—C5—C6	−166.5 (3)	S2—C10—C11—C8	0.0 (4)
O2—S1—C5—C6	−35.5 (4)	C9—C8—C11—C10	0.4 (4)
N1—S1—C5—C6	77.3 (4)	N1—C8—C11—C10	172.4 (3)
O1—S1—C5—C4	15.8 (4)	C9—C8—C11—C17	−174.7 (3)
O2—S1—C5—C4	146.9 (3)	N1—C8—C11—C17	−2.7 (6)
N1—S1—C5—C4	−100.4 (3)	C13—O3—C12—O4	−0.1 (5)
C4—C5—C6—C7	0.7 (7)	C13—O3—C12—C9	178.8 (3)
S1—C5—C6—C7	−176.9 (3)	C8—C9—C12—O4	2.4 (6)
C5—C6—C7—C2	0.6 (7)	S2—C9—C12—O4	176.2 (3)
C3—C2—C7—C6	−1.2 (7)	C8—C9—C12—O3	−176.5 (3)
C1—C2—C7—C6	173.9 (4)	S2—C9—C12—O3	−2.7 (4)
S1—N1—C8—C9	−115.8 (4)	C12—O3—C13—C14	−178.0 (3)
S1—N1—C8—C11	73.0 (4)	C10—N2—C15—C16	−2.2 (7)
N1—C8—C9—C12	1.5 (6)	N2—C15—C16—C17	1.0 (7)
C11—C8—C9—C12	173.5 (3)	C15—C16—C17—C11	−0.4 (6)
N1—C8—C9—S2	−172.6 (3)	C10—C11—C17—C16	1.1 (5)
C11—C8—C9—S2	−0.6 (4)	C8—C11—C17—C16	175.9 (4)
C10—S2—C9—C8	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.95 (3)	2.22 (3)	2.867 (4)	125 (3)
N1—H1N···O2i	0.95 (3)	2.21 (3)	3.033 (4)	145 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.95 (3)	2.22 (3)	2.867 (4)	125 (3)
N1—H1N⋯O2i	0.95 (3)	2.21 (3)	3.033 (4)	145 (3)

Symmetry code: (i) .