organic compounds
In the title compound, C20H19NO4S, the structure is stabilized by intermolecular and intramolecular C—HO hydrogen bonds. The thieno[2,3-b]pyridine moiety is planar.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003222/na6203sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003222/na6203Isup2.hkl |
CCDC reference: 206778
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 |
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) Å3 | Prism, colourless |
Z = 4 | 0.40 × 0.20 × 0.18 mm |
Data collection top
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 F2 > 2σ(F2) | intensity decay: 0.0% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + ( .069P)2 + .8481P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.051 | (Δ/σ)max = 0.001 |
wR(F2) = 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+0.001xFc2λ3/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 | 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 (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. |