2,5-Diethoxy­carbonyl-6-methyl-4-phenyl­thieno­[2,3-b]­pyridine

Novoa de Armas, H.; Peeters, O.M.; Blaton, N.M.; De Ranter, C.J.; Salfrán, E.; Suárez Navarro, M.; Ochoa Rodríguez, E.; Verdecia Reyes, Y.

doi:10.1107/S1600536803003222

2,5-Diethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine

H. Novoa de Armas, O. M. Peeters, N. M. Blaton, C. J. De Ranter, E. Salfrán, M. Suárez Navarro, E. Ochoa Rodríguez and Y. Verdecia Reyes

In the title compound, C₂₀H₁₉NO₄S, the structure is stabilized by intermolecular and intramolecular C—H

O hydrogen bonds. The thieno[2,3-b]pyridine moiety is planar.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003222/na6203sup1.cif Contains datablocks X, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003222/na6203Isup2.hkl Contains datablock I

CCDC reference: 206778

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.051
wR factor = 0.148
Data-to-parameter ratio = 14.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_360  Alert B Short  C(sp3)-C(sp3) Bond  C(24)  -   C(25)  =       1.33 Ang.


 Alert Level C:



CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          

PLAT_715  Alert C D-H     Unknown or Inconsistent Label ........       H24
                           C24    H24

PLAT_716  Alert C H...A   Unknown or Inconsistent Label ........       H24
                           H24    O22

PLAT_718  Alert C D-H..A  Unknown or Inconsistent Label ........       H24
                           C24    H24    O22


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 24 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 1990), PARST (Nardelli, 1995), PARSTCIF (Nardelli, 1991).

2,5-diethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine top

Crystal data top

C₂₀H₁₉NO₄S	F(000) = 776
M_r = 369.42	D_x = 1.314 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
a = 7.7809 (4) Å	Cell parameters from 38 reflections
b = 9.8572 (4) Å	θ = 11.0–28.0°
c = 24.548 (1) Å	µ = 1.75 mm⁻¹
β = 97.222 (5)°	T = 293 K
V = 1867.8 (2) Å³	Prism, colourless
Z = 4	0.40 × 0.20 × 0.18 mm

Data collection top

Siemens P4 four-circle diffractometer	R_int = 0.047
ω/2θ scan	θ_max = 69.3°
Absorption correction: ψ scan (North, Phillips & Mathews, 1968)	h = −1→9
T_min = 0.529, T_max = 0.730	k = −11→1
4884 measured reflections	l = −29→29
3411 independent reflections	3 standard reflections every 100 reflections
2824 reflections with F² > 2σ(F²)	intensity decay: 0.0%

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + ( .069P)² + .8481P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.051	(Δ/σ)_max = 0.001
wR(F²) = 0.148	Δρ_max = 0.29 e Å⁻³
S = 1.05	Δρ_min = −0.39 e Å⁻³
3411 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin((2θ)]^-1/4
239 parameters	Extinction coefficient: 0.0043 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.67728 (9)	−0.03738 (7)	0.42079 (2)	0.0593 (2)*
C2	0.6412 (3)	0.1248 (3)	0.44410 (10)	0.0548 (8)*
C21	0.5671 (4)	0.2240 (3)	0.40300 (10)	0.0651 (9)*
O22	0.5285 (3)	0.1987 (3)	0.35513 (8)	0.0865 (8)*
O23	0.5539 (3)	0.3461 (2)	0.42535 (9)	0.0839 (8)*
C24	0.4888 (6)	0.4539 (4)	0.3878 (2)	0.111 (2)*
C25	0.5363 (9)	0.5762 (4)	0.4075 (3)	0.205 (4)*
C3	0.6899 (3)	0.1420 (3)	0.49870 (10)	0.0526 (8)*
C3A	0.7629 (3)	0.0219 (2)	0.52452 (9)	0.0461 (7)*
C4	0.8284 (3)	−0.0054 (2)	0.57944 (9)	0.0465 (8)*
C41	0.8281 (3)	0.1005 (2)	0.62247 (9)	0.0476 (7)*
C42	0.7434 (3)	0.0779 (3)	0.66830 (10)	0.0571 (9)*
C43	0.7477 (4)	0.1754 (3)	0.70900 (10)	0.0720 (10)*
C44	0.8359 (5)	0.2946 (3)	0.70450 (10)	0.0790 (10)*
C45	0.9176 (4)	0.3187 (3)	0.65900 (10)	0.0720 (10)*
C46	0.9144 (3)	0.2229 (3)	0.61770 (10)	0.0570 (8)*
C5	0.8900 (3)	−0.1368 (2)	0.59119 (9)	0.0474 (7)*
C51	0.9657 (3)	−0.1759 (3)	0.64810 (10)	0.0526 (8)*
O52	0.9260 (3)	−0.2752 (2)	0.67210 (7)	0.0773 (8)*
O53	1.0838 (2)	−0.0868 (2)	0.66851 (7)	0.0607 (6)*
C54	1.1599 (4)	−0.1019 (3)	0.72530 (10)	0.0770 (10)*
C55	1.2486 (6)	0.0263 (4)	0.7409 (2)	0.099 (2)*
C6	0.8876 (3)	−0.2353 (2)	0.54920 (10)	0.0532 (8)*
C61	0.9615 (5)	−0.3753 (3)	0.55920 (10)	0.0780 (10)*
N7	0.8249 (3)	−0.2099 (2)	0.49702 (8)	0.0563 (7)*
C7A	0.7637 (3)	−0.0847 (2)	0.48627 (9)	0.0486 (7)*
H24A	0.5323	0.4407	0.3529	0.133*
H24B	0.3633	0.4491	0.3815	0.133*
H25A	0.4993	0.5875	0.4431	0.246*
H25B	0.4837	0.6447	0.3831	0.246*
H25C	0.6601	0.5844	0.4105	0.246*
H3	0.6771	0.2229	0.5172	0.063*
H42	0.6837	−0.0029	0.6715	0.068*
H43	0.6907	0.1601	0.7395	0.087*
H44	0.8402	0.3591	0.7322	0.094*
H45	0.9756	0.4003	0.6559	0.086*
H46	0.9697	0.2401	0.587	0.068*
H54A	1.2416	−0.1767	0.7288	0.092*
H54B	1.0706	−0.1197	0.7486	0.092*
H55A	1.3368	0.0424	0.7176	0.119*
H55B	1.3007	0.0211	0.7785	0.119*
H55C	1.1664	0.0993	0.7369	0.119*
H61A	0.9013	−0.4212	0.5856	0.094*
H61B	1.0823	−0.3688	0.5729	0.094*
H61C	0.9481	−0.4254	0.5254	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0656 (4)	0.0702 (4)	0.0415 (3)	−0.0051 (3)	0.0041 (3)	−0.0030 (3)
C2	0.0520 (10)	0.063 (2)	0.0490 (10)	−0.0030 (10)	0.0040 (10)	0.0070 (10)
C21	0.060 (2)	0.069 (2)	0.064 (2)	−0.0060 (10)	0.0000 (10)	0.0120 (10)
O22	0.097 (2)	0.098 (2)	0.0590 (10)	0.0060 (10)	−0.0120 (10)	0.0150 (10)
O23	0.094 (2)	0.0670 (10)	0.0830 (10)	0.0030 (10)	−0.0180 (10)	0.0150 (10)
C24	0.116 (3)	0.074 (2)	0.128 (3)	0.002 (2)	−0.039 (3)	0.031 (2)
C25	0.254 (7)	0.062 (3)	0.250 (7)	0.011 (4)	−0.160 (6)	0.005 (4)
C3	0.0540 (10)	0.0510 (10)	0.0520 (10)	−0.0020 (10)	0.0040 (10)	0.0010 (10)
C3A	0.0490 (10)	0.0480 (10)	0.0420 (10)	−0.0040 (10)	0.0082 (9)	−0.0022 (9)
C4	0.0500 (10)	0.0470 (10)	0.0430 (10)	−0.0050 (10)	0.0088 (9)	−0.0014 (9)
C41	0.0550 (10)	0.0460 (10)	0.0410 (10)	0.0030 (10)	0.0014 (9)	−0.0026 (9)
C42	0.066 (2)	0.0590 (10)	0.0470 (10)	−0.0010 (10)	0.0110 (10)	−0.0040 (10)
C43	0.085 (2)	0.082 (2)	0.0510 (10)	0.009 (2)	0.0150 (10)	−0.0120 (10)
C44	0.105 (2)	0.068 (2)	0.061 (2)	0.013 (2)	−0.001 (2)	−0.0240 (10)
C45	0.095 (2)	0.0490 (10)	0.066 (2)	−0.0050 (10)	−0.008 (2)	−0.0100 (10)
C46	0.071 (2)	0.0490 (10)	0.0500 (10)	−0.0030 (10)	0.0030 (10)	−0.0020 (10)
C5	0.0540 (10)	0.0440 (10)	0.0450 (10)	−0.0050 (10)	0.0093 (9)	0.0014 (9)
C51	0.0650 (10)	0.0460 (10)	0.0480 (10)	−0.0010 (10)	0.0120 (10)	0.0040 (10)
O52	0.106 (2)	0.0620 (10)	0.0620 (10)	−0.0180 (10)	0.0050 (10)	0.0170 (10)
O53	0.0690 (10)	0.0590 (10)	0.0511 (9)	−0.0088 (9)	−0.0057 (8)	0.0097 (8)
C54	0.096 (2)	0.075 (2)	0.054 (2)	−0.003 (2)	−0.0140 (10)	0.0090 (10)
C55	0.115 (3)	0.089 (3)	0.081 (2)	−0.008 (2)	−0.032 (2)	−0.004 (2)
C6	0.0640 (10)	0.0450 (10)	0.0520 (10)	−0.0030 (10)	0.0130 (10)	−0.0020 (10)
C61	0.114 (3)	0.050 (2)	0.071 (2)	0.011 (2)	0.015 (2)	−0.0050 (10)
N7	0.0680 (10)	0.0520 (10)	0.0500 (10)	−0.0040 (10)	0.0105 (9)	−0.0066 (9)
C7A	0.0510 (10)	0.0530 (10)	0.0430 (10)	−0.0070 (10)	0.0098 (9)	−0.0040 (10)

Geometric parameters (Å, º) top

S1—C2	1.732 (3)	C43—C44	1.372 (5)
S1—C7A	1.727 (2)	C44—H44	0.93
C2—C21	1.470 (4)	C44—C45	1.373 (5)
C2—C3	1.358 (3)	C45—H45	0.93
C21—O22	1.202 (4)	C45—C46	1.383 (4)
C21—O23	1.332 (4)	C46—H46	0.93
O23—C24	1.454 (5)	C5—C51	1.496 (3)
C24—H24A	0.97	C5—C6	1.414 (3)
C24—H24B	0.97	C51—O52	1.203 (3)
C24—C25	1.334 (6)	C51—O53	1.324 (3)
C25—H25A	0.96	O53—C54	1.451 (3)
C25—H25B	0.96	C54—H54A	0.97
C25—H25C	0.96	C54—H54B	0.97
C3—H3	0.93	C54—C55	1.469 (5)
C3—C3A	1.426 (3)	C55—H55A	0.96
C3A—C4	1.406 (3)	C55—H55B	0.96
C3A—C7A	1.410 (3)	C55—H55C	0.96
C4—C41	1.485 (3)	C6—C61	1.503 (4)
C4—C5	1.399 (3)	C6—N7	1.337 (3)
C41—C42	1.391 (4)	C61—H61A	0.96
C41—C46	1.393 (3)	C61—H61B	0.96
C42—H42	0.93	C61—H61C	0.96
C42—C43	1.384 (4)	N7—C7A	1.337 (3)
C43—H43	0.93

C2—S1—C7A	90.10 (10)	H44—C44—C45	120
S1—C2—C21	117.0 (2)	C44—C45—H45	119.7
S1—C2—C3	113.8 (2)	C44—C45—C46	120.6 (3)
C21—C2—C3	129.1 (2)	H45—C45—C46	119.7
C2—C21—O22	124.1 (3)	C41—C46—C45	119.7 (2)
C2—C21—O23	111.3 (3)	C41—C46—H46	120.2
O22—C21—O23	124.6 (3)	C45—C46—H46	120.2
C21—O23—C24	116.0 (3)	C4—C5—C51	121.0 (2)
O23—C24—H24A	109.2	C4—C5—C6	120.9 (2)
O23—C24—H24B	109.2	C51—C5—C6	118.1 (2)
O23—C24—C25	111.9 (3)	C5—C51—O52	124.9 (2)
H24A—C24—H24B	107.9	C5—C51—O53	110.9 (2)
H24A—C24—C25	109.2	O52—C51—O53	124.2 (2)
H24B—C24—C25	109.2	C51—O53—C54	118.4 (2)
C24—C25—H25A	109.5	O53—C54—H54A	110.4
C24—C25—H25B	109.5	O53—C54—H54B	110.4
C24—C25—H25C	109.5	O53—C54—C55	106.5 (2)
H25A—C25—H25B	109.5	H54A—C54—H54B	108.6
H25A—C25—H25C	109.5	H54A—C54—C55	110.4
H25B—C25—H25C	109.5	H54B—C54—C55	110.4
C2—C3—H3	123.8	C54—C55—H55A	109.5
C2—C3—C3A	112.4 (2)	C54—C55—H55B	109.5
H3—C3—C3A	123.8	C54—C55—H55C	109.5
C3—C3A—C4	131.4 (2)	H55A—C55—H55B	109.5
C3—C3A—C7A	111.0 (2)	H55A—C55—H55C	109.5
C4—C3A—C7A	117.7 (2)	H55B—C55—H55C	109.5
C3A—C4—C41	121.0 (2)	C5—C6—C61	122.8 (2)
C3A—C4—C5	116.7 (2)	C5—C6—N7	122.6 (2)
C41—C4—C5	122.4 (2)	C61—C6—N7	114.5 (2)
C4—C41—C42	120.4 (2)	C6—C61—H61A	109.5
C4—C41—C46	120.4 (2)	C6—C61—H61B	109.5
C42—C41—C46	119.2 (2)	C6—C61—H61C	109.5
C41—C42—H42	119.9	H61A—C61—H61B	109.5
C41—C42—C43	120.1 (2)	H61A—C61—H61C	109.5
H42—C42—C43	120	H61B—C61—H61C	109.5
C42—C43—H43	119.9	C6—N7—C7A	116.1 (2)
C42—C43—C44	120.3 (3)	S1—C7A—C3A	112.6 (2)
H43—C43—C44	119.9	S1—C7A—N7	121.4 (2)
C43—C44—H44	119.9	C3A—C7A—N7	126.0 (2)
C43—C44—C45	120.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···O22ⁱ	0.93	2.57	3.455 (4)	159
C43—H43···O52ⁱⁱ	0.93	2.54	3.403 (3)	155
C61—H61A···O52	0.96	2.55	2.987 (4)	108
C24—H24···O22	0.97	2.39	2.670 (5)	96

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+3/2.

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2,5-Diethoxy­carbonyl-6-methyl-4-phenyl­thieno­[2,3-b]­pyridine

Supporting information

Key indicators

checkCIF results

2,5-Diethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine