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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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

Crystal data

C20H19NO4S	F(000) = 776
Mr = 369.42	Dx = 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) Å^3	Prism, colourless
Z = 4	0.40 × 0.20 × 0.18 mm

Data collection

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

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + ( .069P)^2 + .8481P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.051	(Δ/σ)max = 0.001
wR(F^2) = 0.148	Δρmax = 0.29 e Å^−3
S = 1.05	Δρmin = −0.39 e Å^−3
3411 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin((2θ)]^-1/4
239 parameters	Extinction coefficient: 0.0043 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···O22^i	0.93	2.57	3.455 (4)	159
C43—H43···O52^ii	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.