Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018786/om6165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018786/om6165Isup2.hkl |
CCDC reference: 222914
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.137
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 12 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O5 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C11 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C12' PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7' PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C4 - C5 = 1.35 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H31 .. H33E = 1.81 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
A mixture of 2-(4-methoxy-benzylidene)-7-methyl-3-oxo-5-phenyl- 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) was refluxed in methanol (60 ml) until the disappearence of the starting material, as evidenced by thin-layer chromatography. When the reaction was complete, the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1), giving the title compound (I) (m.p. 479–481 K); IR (KBr): 3351.4 (–NH), 1743.4, 1723.1, 1688.2 (C═O) cm−1; 1H NMR (δ, p.p.m.): 1.03 (m, 3H, –CH3), 2.17 (s, 3H, –CH3), 2.23 (s, 3H, N—CH3), 3.45 (m, 1H,-CH2), 3.73 (s, 3H, –CH3), 3.99 (m, 1H, –CH2), 4.03 (m, 2H, –CH2), 4.57 (m, 1H, –CH), 5.72 (s, 1H, –CH), 6.69–7.74 (m, 13H, ArH), 7.86 (bs, 1H, –NH). 20 mg of (I) was dissolved in 15 ml dioxane; the solution was kept at room temperature for 15 d and natural evaporation gave colorless single crystals of (I), suitable for X-ray analysis.
H atoms were positioned geometrically and allowed for in the riding model approximation [C—H = 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C)]. Atom C6 and the atoms of the attached phenyl ring are disordered over two sites. The ratio of site occupancies from the refinement was 0.64:0.36 (17).
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. H atoms have been omitted for clarity. | |
Fig. 2. The crystal structure of (I), viewed along the b axis. |
C34H32N4O5S | Dx = 1.332 Mg m−3 |
Mr = 608.70 | Melting point: 481 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.990 (6) Å | Cell parameters from 816 reflections |
b = 11.375 (5) Å | θ = 2.3–25.3° |
c = 17.815 (8) Å | µ = 0.16 mm−1 |
β = 92.254 (6)° | T = 293 K |
V = 3035 (2) Å3 | Block, colorless |
Z = 4 | 0.38 × 0.30 × 0.24 mm |
F(000) = 1280 |
Bruker SMART CCD area-detector diffractometer | 6236 independent reflections |
Radiation source: fine-focus sealed tube | 3567 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −18→12 |
Tmin = 0.905, Tmax = 0.960 | k = −14→6 |
14013 measured reflections | l = −21→22 |
Refinement on F2 | 278 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.34 e Å−3 |
6236 reflections | Δρmin = −0.40 e Å−3 |
413 parameters |
C34H32N4O5S | V = 3035 (2) Å3 |
Mr = 608.70 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.990 (6) Å | µ = 0.16 mm−1 |
b = 11.375 (5) Å | T = 293 K |
c = 17.815 (8) Å | 0.38 × 0.30 × 0.24 mm |
β = 92.254 (6)° |
Bruker SMART CCD area-detector diffractometer | 6236 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 3567 reflections with I > 2σ(I) |
Tmin = 0.905, Tmax = 0.960 | Rint = 0.042 |
14013 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 278 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.34 e Å−3 |
6236 reflections | Δρmin = −0.40 e Å−3 |
413 parameters |
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 | Occ. (<1) | |
S1 | −0.11674 (4) | 0.75530 (6) | 0.22105 (4) | 0.03688 (18) | |
N1 | 0.02404 (12) | 0.74525 (17) | 0.30997 (10) | 0.0328 (5) | |
N2 | −0.05077 (13) | 0.56453 (18) | 0.28956 (11) | 0.0365 (5) | |
N3 | −0.07997 (15) | 1.09805 (18) | 0.21885 (13) | 0.0474 (6) | |
N4 | −0.27194 (14) | 0.98711 (19) | 0.28112 (12) | 0.0431 (6) | |
H4 | −0.3290 | 0.9802 | 0.2758 | 0.052* | |
O1 | 0.07145 (12) | 0.93404 (15) | 0.32201 (11) | 0.0503 (5) | |
O2 | −0.23486 (13) | 0.94136 (17) | 0.16092 (11) | 0.0553 (5) | |
O3 | 0.20107 (18) | 0.5915 (2) | 0.46174 (15) | 0.0943 (9) | |
O4 | 0.12615 (14) | 0.42263 (17) | 0.46218 (11) | 0.0612 (6) | |
O5 | 0.03469 (17) | 0.6091 (2) | −0.07219 (14) | 0.0942 (7) | |
C1 | −0.05440 (16) | 0.8931 (2) | 0.23480 (13) | 0.0345 (6) | |
C2 | 0.01901 (16) | 0.8643 (2) | 0.29439 (14) | 0.0353 (6) | |
C3 | −0.04170 (15) | 0.6752 (2) | 0.27775 (13) | 0.0320 (6) | |
C4 | 0.00562 (17) | 0.5144 (2) | 0.34725 (14) | 0.0391 (6) | |
C5 | 0.07689 (18) | 0.5719 (2) | 0.37727 (14) | 0.0395 (6) | |
C6 | 0.10410 (16) | 0.6913 (2) | 0.34741 (14) | 0.0381 (6) | 0.658 (5) |
H6A | 0.1233 | 0.7409 | 0.3900 | 0.046* | 0.658 (5) |
C7 | 0.1797 (2) | 0.6886 (4) | 0.2903 (2) | 0.047 (3) | 0.658 (5) |
C8 | 0.1881 (3) | 0.5908 (3) | 0.2443 (3) | 0.0642 (19) | 0.658 (5) |
H8A | 0.1498 | 0.5272 | 0.2489 | 0.077* | 0.658 (5) |
C9 | 0.2538 (4) | 0.5882 (4) | 0.1914 (3) | 0.090 (3) | 0.658 (5) |
H9A | 0.2594 | 0.5227 | 0.1606 | 0.108* | 0.658 (5) |
C10 | 0.3112 (3) | 0.6832 (5) | 0.1845 (2) | 0.084 (2) | 0.658 (5) |
H10A | 0.3551 | 0.6815 | 0.1491 | 0.101* | 0.658 (5) |
C11 | 0.3028 (2) | 0.7810 (4) | 0.2305 (3) | 0.097 (2) | 0.658 (5) |
H11A | 0.3412 | 0.8446 | 0.2259 | 0.117* | 0.658 (5) |
C12 | 0.2371 (3) | 0.7837 (4) | 0.2834 (2) | 0.0725 (17) | 0.658 (5) |
H12A | 0.2315 | 0.8491 | 0.3142 | 0.087* | 0.658 (5) |
C6' | 0.10410 (16) | 0.6913 (2) | 0.34741 (14) | 0.0381 (6) | 0.342 (5) |
H6'A | 0.1223 | 0.7407 | 0.3904 | 0.046* | 0.342 (5) |
C7' | 0.1812 (4) | 0.6830 (6) | 0.2968 (4) | 0.041 (5) | 0.342 (5) |
C8' | 0.1718 (4) | 0.6392 (6) | 0.2240 (5) | 0.058 (3) | 0.342 (5) |
H8'A | 0.1160 | 0.6154 | 0.2050 | 0.070* | 0.342 (5) |
C9' | 0.2458 (6) | 0.6311 (7) | 0.1797 (4) | 0.067 (4) | 0.342 (5) |
H9'A | 0.2395 | 0.6019 | 0.1310 | 0.081* | 0.342 (5) |
C10' | 0.3292 (5) | 0.6668 (7) | 0.2081 (5) | 0.093 (3) | 0.342 (5) |
H10B | 0.3787 | 0.6614 | 0.1784 | 0.111* | 0.342 (5) |
C11' | 0.3385 (4) | 0.7105 (6) | 0.2808 (5) | 0.093 (3) | 0.342 (5) |
H11B | 0.3943 | 0.7344 | 0.2998 | 0.111* | 0.342 (5) |
C12' | 0.2645 (5) | 0.7186 (6) | 0.3252 (4) | 0.093 (3) | 0.342 (5) |
H12B | 0.2708 | 0.7479 | 0.3738 | 0.111* | 0.342 (5) |
C13 | −0.0284 (2) | 0.3944 (2) | 0.36847 (18) | 0.0591 (8) | |
H13A | −0.0106 | 0.3376 | 0.3321 | 0.089* | |
H13B | −0.0923 | 0.3962 | 0.3697 | 0.089* | |
H13C | −0.0038 | 0.3730 | 0.4171 | 0.089* | |
C14 | 0.1404 (2) | 0.5307 (3) | 0.43740 (16) | 0.0513 (8) | |
C15 | 0.1859 (2) | 0.3789 (3) | 0.52163 (17) | 0.0701 (10) | |
H15A | 0.1857 | 0.4309 | 0.5648 | 0.084* | |
H15B | 0.2464 | 0.3738 | 0.5044 | 0.084* | |
C16 | 0.1526 (3) | 0.2599 (3) | 0.54209 (19) | 0.0840 (12) | |
H16A | 0.0920 | 0.2659 | 0.5571 | 0.126* | |
H16B | 0.1892 | 0.2288 | 0.5828 | 0.126* | |
H16C | 0.1553 | 0.2086 | 0.4995 | 0.126* | |
C17 | −0.00573 (18) | 0.9410 (2) | 0.16225 (15) | 0.0436 (7) | |
H17 | 0.0556 | 0.9604 | 0.1788 | 0.052* | |
C18 | −0.0527 (2) | 1.0573 (2) | 0.14542 (17) | 0.0578 (8) | |
H18A | −0.0124 | 1.1131 | 0.1233 | 0.069* | |
H18B | −0.1042 | 1.0460 | 0.1114 | 0.069* | |
C19 | −0.11784 (17) | 0.9959 (2) | 0.25715 (14) | 0.0363 (6) | |
C20 | −0.21457 (18) | 0.9697 (2) | 0.22538 (15) | 0.0392 (6) | |
C21 | −0.22645 (18) | 1.0180 (2) | 0.34904 (15) | 0.0412 (6) | |
C22 | −0.2631 (2) | 1.0460 (3) | 0.41660 (17) | 0.0610 (9) | |
H22 | −0.3245 | 1.0432 | 0.4224 | 0.073* | |
C23 | −0.2051 (2) | 1.0782 (3) | 0.47544 (18) | 0.0732 (10) | |
H23 | −0.2279 | 1.0959 | 0.5219 | 0.088* | |
C24 | −0.1146 (2) | 1.0845 (3) | 0.46657 (18) | 0.0698 (10) | |
H24 | −0.0771 | 1.1071 | 0.5069 | 0.084* | |
C25 | −0.0783 (2) | 1.0577 (2) | 0.39801 (16) | 0.0523 (8) | |
H25 | −0.0172 | 1.0637 | 0.3919 | 0.063* | |
C26 | −0.13495 (17) | 1.0217 (2) | 0.33891 (14) | 0.0373 (6) | |
C27 | 0.00084 (18) | 0.8565 (2) | 0.09764 (15) | 0.0442 (7) | |
C28 | 0.0820 (2) | 0.8029 (3) | 0.08501 (17) | 0.0561 (8) | |
H28 | 0.1314 | 0.8220 | 0.1158 | 0.067* | |
C29 | 0.0914 (2) | 0.7219 (3) | 0.02809 (19) | 0.0652 (9) | |
H29 | 0.1467 | 0.6877 | 0.0205 | 0.078* | |
C30 | 0.0184 (2) | 0.6924 (3) | −0.01728 (16) | 0.0581 (8) | |
C31 | −0.0630 (2) | 0.7450 (3) | −0.00677 (16) | 0.0598 (8) | |
H31 | −0.1123 | 0.7258 | −0.0377 | 0.072* | |
C32 | −0.0709 (2) | 0.8272 (3) | 0.05051 (15) | 0.0560 (8) | |
H32 | −0.1257 | 0.8632 | 0.0571 | 0.067* | |
C33 | −0.0371 (3) | 0.5658 (4) | −0.1143 (2) | 0.0942 (7) | |
H33A | −0.0165 | 0.5093 | −0.1498 | 0.141* | 0.658 (5) |
H33B | −0.0666 | 0.6292 | −0.1408 | 0.141* | 0.658 (5) |
H33C | −0.0781 | 0.5286 | −0.0817 | 0.141* | 0.658 (5) |
H33D | −0.0293 | 0.5828 | −0.1664 | 0.141* | 0.342 (5) |
H33E | −0.0910 | 0.6021 | −0.0984 | 0.141* | 0.342 (5) |
H33F | −0.0408 | 0.4822 | −0.1074 | 0.141* | 0.342 (5) |
C34 | −0.1376 (2) | 1.2022 (2) | 0.21455 (18) | 0.0631 (9) | |
H34A | −0.1901 | 1.1851 | 0.1838 | 0.095* | |
H34B | −0.1058 | 1.2663 | 0.1929 | 0.095* | |
H34C | −0.1547 | 1.2235 | 0.2641 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0340 (4) | 0.0352 (3) | 0.0407 (4) | −0.0008 (3) | −0.0073 (3) | 0.0035 (3) |
N1 | 0.0254 (11) | 0.0337 (11) | 0.0389 (11) | 0.0001 (10) | −0.0039 (9) | −0.0023 (10) |
N2 | 0.0350 (12) | 0.0328 (12) | 0.0410 (12) | −0.0001 (10) | −0.0068 (10) | 0.0021 (10) |
N3 | 0.0530 (15) | 0.0327 (12) | 0.0572 (15) | 0.0043 (11) | 0.0101 (12) | 0.0077 (11) |
N4 | 0.0292 (12) | 0.0477 (14) | 0.0519 (14) | 0.0019 (10) | −0.0058 (11) | −0.0015 (11) |
O1 | 0.0392 (11) | 0.0379 (11) | 0.0727 (13) | −0.0061 (9) | −0.0105 (10) | −0.0039 (10) |
O2 | 0.0518 (13) | 0.0663 (14) | 0.0467 (12) | 0.0125 (10) | −0.0128 (10) | −0.0062 (10) |
O3 | 0.100 (2) | 0.0732 (17) | 0.1042 (19) | −0.0144 (15) | −0.0672 (16) | 0.0175 (14) |
O4 | 0.0698 (14) | 0.0510 (13) | 0.0604 (13) | 0.0046 (11) | −0.0274 (11) | 0.0133 (10) |
O5 | 0.0910 (17) | 0.1129 (18) | 0.0796 (15) | −0.0157 (14) | 0.0152 (12) | −0.0361 (13) |
C1 | 0.0301 (14) | 0.0331 (14) | 0.0401 (14) | −0.0037 (11) | −0.0003 (11) | 0.0039 (11) |
C2 | 0.0295 (14) | 0.0329 (14) | 0.0439 (15) | 0.0002 (12) | 0.0050 (11) | −0.0015 (12) |
C3 | 0.0273 (14) | 0.0365 (14) | 0.0321 (13) | 0.0012 (11) | −0.0007 (10) | −0.0019 (11) |
C4 | 0.0388 (16) | 0.0376 (15) | 0.0404 (15) | 0.0052 (13) | −0.0033 (12) | 0.0018 (12) |
C5 | 0.0418 (16) | 0.0380 (15) | 0.0381 (14) | 0.0042 (13) | −0.0072 (12) | −0.0006 (12) |
C6 | 0.0353 (15) | 0.0357 (14) | 0.0421 (15) | 0.0046 (12) | −0.0136 (12) | −0.0065 (12) |
C7 | 0.028 (6) | 0.054 (6) | 0.058 (5) | 0.006 (5) | −0.009 (4) | −0.004 (5) |
C8 | 0.056 (3) | 0.072 (4) | 0.065 (4) | 0.006 (3) | 0.010 (3) | −0.009 (3) |
C9 | 0.073 (5) | 0.106 (6) | 0.092 (5) | 0.012 (4) | 0.024 (4) | −0.025 (4) |
C10 | 0.042 (4) | 0.127 (6) | 0.086 (4) | 0.009 (4) | 0.024 (3) | 0.001 (4) |
C11 | 0.059 (4) | 0.115 (6) | 0.121 (5) | −0.017 (4) | 0.038 (4) | −0.005 (4) |
C12 | 0.049 (3) | 0.077 (4) | 0.094 (4) | −0.013 (3) | 0.022 (3) | −0.014 (3) |
C6' | 0.0353 (15) | 0.0357 (14) | 0.0421 (15) | 0.0046 (12) | −0.0136 (12) | −0.0065 (12) |
C7' | 0.033 (11) | 0.029 (9) | 0.060 (9) | 0.003 (8) | −0.005 (8) | −0.002 (8) |
C8' | 0.054 (7) | 0.065 (7) | 0.056 (6) | −0.029 (6) | 0.001 (5) | 0.001 (6) |
C9' | 0.081 (9) | 0.059 (7) | 0.063 (7) | −0.004 (6) | 0.028 (7) | 0.002 (5) |
C10' | 0.040 (4) | 0.090 (5) | 0.149 (7) | 0.011 (4) | 0.005 (4) | −0.029 (5) |
C11' | 0.040 (4) | 0.090 (5) | 0.149 (7) | 0.011 (4) | 0.005 (4) | −0.029 (5) |
C12' | 0.040 (4) | 0.090 (5) | 0.149 (7) | 0.011 (4) | 0.005 (4) | −0.029 (5) |
C13 | 0.057 (2) | 0.0452 (18) | 0.074 (2) | −0.0036 (15) | −0.0166 (16) | 0.0173 (16) |
C14 | 0.056 (2) | 0.0482 (18) | 0.0487 (17) | 0.0060 (16) | −0.0149 (15) | −0.0016 (15) |
C15 | 0.082 (2) | 0.069 (2) | 0.056 (2) | 0.0183 (19) | −0.0275 (18) | 0.0101 (17) |
C16 | 0.104 (3) | 0.075 (3) | 0.071 (2) | 0.011 (2) | −0.015 (2) | 0.023 (2) |
C17 | 0.0422 (16) | 0.0406 (15) | 0.0486 (16) | −0.0024 (13) | 0.0110 (13) | 0.0047 (13) |
C18 | 0.070 (2) | 0.0462 (18) | 0.0581 (19) | 0.0055 (16) | 0.0193 (16) | 0.0151 (15) |
C19 | 0.0353 (15) | 0.0341 (14) | 0.0392 (14) | 0.0014 (11) | −0.0012 (11) | 0.0018 (11) |
C20 | 0.0416 (16) | 0.0347 (14) | 0.0410 (16) | 0.0073 (12) | −0.0045 (13) | 0.0015 (12) |
C21 | 0.0410 (17) | 0.0366 (15) | 0.0460 (16) | 0.0036 (12) | 0.0027 (13) | 0.0015 (13) |
C22 | 0.0494 (19) | 0.075 (2) | 0.059 (2) | 0.0085 (17) | 0.0105 (16) | −0.0054 (17) |
C23 | 0.078 (3) | 0.096 (3) | 0.0467 (19) | 0.016 (2) | 0.0107 (18) | −0.0128 (18) |
C24 | 0.071 (2) | 0.084 (3) | 0.053 (2) | 0.016 (2) | −0.0113 (17) | −0.0245 (18) |
C25 | 0.0449 (18) | 0.0538 (18) | 0.0577 (19) | 0.0055 (14) | −0.0058 (15) | −0.0114 (15) |
C26 | 0.0369 (15) | 0.0334 (14) | 0.0416 (15) | 0.0046 (12) | 0.0004 (12) | −0.0007 (12) |
C27 | 0.0431 (17) | 0.0491 (17) | 0.0409 (15) | −0.0011 (14) | 0.0096 (13) | 0.0077 (13) |
C28 | 0.0470 (19) | 0.0584 (19) | 0.063 (2) | 0.0026 (16) | 0.0045 (15) | −0.0049 (16) |
C29 | 0.052 (2) | 0.068 (2) | 0.076 (2) | 0.0061 (17) | 0.0143 (18) | −0.0125 (18) |
C30 | 0.064 (2) | 0.064 (2) | 0.0473 (18) | −0.0087 (18) | 0.0187 (16) | −0.0064 (16) |
C31 | 0.056 (2) | 0.085 (2) | 0.0382 (16) | −0.0117 (19) | 0.0021 (14) | 0.0019 (17) |
C32 | 0.0488 (19) | 0.076 (2) | 0.0437 (17) | 0.0032 (16) | 0.0098 (14) | 0.0017 (16) |
C33 | 0.0910 (17) | 0.1129 (18) | 0.0796 (15) | −0.0157 (14) | 0.0152 (12) | −0.0361 (13) |
C34 | 0.075 (2) | 0.0372 (16) | 0.077 (2) | 0.0126 (16) | 0.0083 (18) | 0.0093 (16) |
S1—C3 | 1.740 (2) | C11'—C12' | 1.3900 |
S1—C1 | 1.836 (2) | C11'—H11B | 0.9300 |
N1—C3 | 1.375 (3) | C12'—H12B | 0.9300 |
N1—C2 | 1.384 (3) | C13—H13A | 0.9600 |
N1—C6 | 1.483 (3) | C13—H13B | 0.9600 |
N2—C3 | 1.284 (3) | C13—H13C | 0.9600 |
N2—C4 | 1.424 (3) | C15—C16 | 1.492 (5) |
N3—C18 | 1.461 (3) | C15—H15A | 0.9700 |
N3—C34 | 1.467 (3) | C15—H15B | 0.9700 |
N3—C19 | 1.472 (3) | C16—H16A | 0.9600 |
N4—C20 | 1.354 (3) | C16—H16B | 0.9600 |
N4—C21 | 1.410 (3) | C16—H16C | 0.9600 |
N4—H4 | 0.8600 | C17—C27 | 1.505 (4) |
O1—C2 | 1.208 (3) | C17—C18 | 1.523 (4) |
O2—C20 | 1.220 (3) | C17—H17 | 0.9800 |
O3—C14 | 1.209 (3) | C18—H18A | 0.9700 |
O4—C14 | 1.327 (3) | C18—H18B | 0.9700 |
O4—C15 | 1.448 (3) | C19—C26 | 1.517 (3) |
O5—C33 | 1.378 (4) | C19—C20 | 1.564 (4) |
O5—C30 | 1.390 (4) | C21—C22 | 1.380 (4) |
C1—C2 | 1.534 (3) | C21—C26 | 1.391 (4) |
C1—C19 | 1.569 (3) | C22—C23 | 1.385 (4) |
C1—C17 | 1.604 (3) | C22—H22 | 0.9300 |
C4—C5 | 1.345 (3) | C23—C24 | 1.375 (5) |
C4—C13 | 1.510 (4) | C23—H23 | 0.9300 |
C5—C14 | 1.481 (4) | C24—C25 | 1.390 (4) |
C5—C6 | 1.520 (4) | C24—H24 | 0.9300 |
C6—C7 | 1.554 (4) | C25—C26 | 1.388 (4) |
C6—H6A | 0.9800 | C25—H25 | 0.9300 |
C7—C8 | 1.3900 | C27—C32 | 1.379 (4) |
C7—C12 | 1.3900 | C27—C28 | 1.387 (4) |
C8—C9 | 1.3900 | C28—C29 | 1.381 (4) |
C8—H8A | 0.9300 | C28—H28 | 0.9300 |
C9—C10 | 1.3900 | C29—C30 | 1.377 (4) |
C9—H9A | 0.9300 | C29—H29 | 0.9300 |
C10—C11 | 1.3900 | C30—C31 | 1.379 (4) |
C10—H10A | 0.9300 | C31—C32 | 1.392 (4) |
C11—C12 | 1.3900 | C31—H31 | 0.9300 |
C11—H11A | 0.9300 | C32—H32 | 0.9300 |
C12—H12A | 0.9300 | C33—H33A | 0.9600 |
C7'—C8' | 1.3900 | C33—H33B | 0.9600 |
C7'—C12' | 1.3900 | C33—H33C | 0.9600 |
C8'—C9' | 1.3900 | C33—H33D | 0.9600 |
C8'—H8'A | 0.9300 | C33—H33E | 0.9600 |
C9'—C10' | 1.3900 | C33—H33F | 0.9600 |
C9'—H9'A | 0.9300 | C34—H34A | 0.9600 |
C10'—C11' | 1.3900 | C34—H34B | 0.9600 |
C10'—H10B | 0.9300 | C34—H34C | 0.9600 |
C3—S1—C1 | 93.18 (11) | H16A—C16—H16B | 109.5 |
C3—N1—C2 | 116.8 (2) | C15—C16—H16C | 109.5 |
C3—N1—C6 | 120.1 (2) | H16A—C16—H16C | 109.5 |
C2—N1—C6 | 122.2 (2) | H16B—C16—H16C | 109.5 |
C3—N2—C4 | 116.6 (2) | C27—C17—C18 | 116.6 (2) |
C18—N3—C34 | 113.2 (2) | C27—C17—C1 | 116.4 (2) |
C18—N3—C19 | 106.9 (2) | C18—C17—C1 | 103.4 (2) |
C34—N3—C19 | 115.1 (2) | C27—C17—H17 | 106.6 |
C20—N4—C21 | 111.5 (2) | C18—C17—H17 | 106.6 |
C20—N4—H4 | 124.3 | C1—C17—H17 | 106.6 |
C21—N4—H4 | 124.3 | N3—C18—C17 | 104.0 (2) |
C14—O4—C15 | 117.3 (2) | N3—C18—H18A | 110.9 |
C33—O5—C30 | 118.1 (3) | C17—C18—H18A | 110.9 |
C2—C1—C19 | 114.2 (2) | N3—C18—H18B | 110.9 |
C2—C1—C17 | 107.1 (2) | C17—C18—H18B | 110.9 |
C19—C1—C17 | 104.52 (19) | H18A—C18—H18B | 109.0 |
C2—C1—S1 | 104.91 (16) | N3—C19—C26 | 112.1 (2) |
C19—C1—S1 | 111.09 (16) | N3—C19—C20 | 110.6 (2) |
C17—C1—S1 | 115.31 (17) | C26—C19—C20 | 101.2 (2) |
O1—C2—N1 | 122.1 (2) | N3—C19—C1 | 102.82 (19) |
O1—C2—C1 | 125.4 (2) | C26—C19—C1 | 121.0 (2) |
N1—C2—C1 | 112.3 (2) | C20—C19—C1 | 109.17 (19) |
N2—C3—N1 | 125.3 (2) | O2—C20—N4 | 126.0 (3) |
N2—C3—S1 | 122.56 (18) | O2—C20—C19 | 125.8 (2) |
N1—C3—S1 | 112.05 (18) | N4—C20—C19 | 108.2 (2) |
C5—C4—N2 | 122.1 (2) | C22—C21—C26 | 122.3 (3) |
C5—C4—C13 | 127.6 (2) | C22—C21—N4 | 127.6 (3) |
N2—C4—C13 | 110.3 (2) | C26—C21—N4 | 110.0 (2) |
C4—C5—C14 | 127.7 (3) | C21—C22—C23 | 117.5 (3) |
C4—C5—C6 | 121.0 (2) | C21—C22—H22 | 121.3 |
C14—C5—C6 | 111.2 (2) | C23—C22—H22 | 121.3 |
N1—C6—C5 | 107.7 (2) | C24—C23—C22 | 121.4 (3) |
N1—C6—C7 | 108.2 (2) | C24—C23—H23 | 119.3 |
C5—C6—C7 | 115.1 (2) | C22—C23—H23 | 119.3 |
N1—C6—H6A | 108.6 | C23—C24—C25 | 120.7 (3) |
C5—C6—H6A | 108.6 | C23—C24—H24 | 119.6 |
C7—C6—H6A | 108.6 | C25—C24—H24 | 119.6 |
C8—C7—C12 | 120.0 | C26—C25—C24 | 118.9 (3) |
C8—C7—C6 | 119.1 (3) | C26—C25—H25 | 120.6 |
C12—C7—C6 | 120.8 (3) | C24—C25—H25 | 120.6 |
C9—C8—C7 | 120.0 | C25—C26—C21 | 119.2 (3) |
C9—C8—H8A | 120.0 | C25—C26—C19 | 131.6 (3) |
C7—C8—H8A | 120.0 | C21—C26—C19 | 108.9 (2) |
C10—C9—C8 | 120.0 | C32—C27—C28 | 117.6 (3) |
C10—C9—H9A | 120.0 | C32—C27—C17 | 123.2 (3) |
C8—C9—H9A | 120.0 | C28—C27—C17 | 119.3 (3) |
C9—C10—C11 | 120.0 | C29—C28—C27 | 121.9 (3) |
C9—C10—H10A | 120.0 | C29—C28—H28 | 119.0 |
C11—C10—H10A | 120.0 | C27—C28—H28 | 119.0 |
C10—C11—C12 | 120.0 | C30—C29—C28 | 119.4 (3) |
C10—C11—H11A | 120.0 | C30—C29—H29 | 120.3 |
C12—C11—H11A | 120.0 | C28—C29—H29 | 120.3 |
C11—C12—C7 | 120.0 | C29—C30—C31 | 120.1 (3) |
C11—C12—H12A | 120.0 | C29—C30—O5 | 114.9 (3) |
C7—C12—H12A | 120.0 | C31—C30—O5 | 124.9 (3) |
C8'—C7'—C12' | 120.0 | C30—C31—C32 | 119.5 (3) |
C7'—C8'—C9' | 120.0 | C30—C31—H31 | 120.3 |
C7'—C8'—H8'A | 120.0 | C32—C31—H31 | 120.3 |
C9'—C8'—H8'A | 120.0 | C27—C32—C31 | 121.5 (3) |
C8'—C9'—C10' | 120.0 | C27—C32—H32 | 119.3 |
C8'—C9'—H9'A | 120.0 | C31—C32—H32 | 119.3 |
C10'—C9'—H9'A | 120.0 | O5—C33—H33A | 109.5 |
C11'—C10'—C9' | 120.0 | O5—C33—H33B | 109.5 |
C11'—C10'—H10B | 120.0 | H33A—C33—H33B | 109.5 |
C9'—C10'—H10B | 120.0 | O5—C33—H33C | 109.5 |
C10'—C11'—C12' | 120.0 | H33A—C33—H33C | 109.5 |
C10'—C11'—H11B | 120.0 | H33B—C33—H33C | 109.5 |
C12'—C11'—H11B | 120.0 | O5—C33—H33D | 109.5 |
C11'—C12'—C7' | 120.0 | H33A—C33—H33D | 56.3 |
C11'—C12'—H12B | 120.0 | H33B—C33—H33D | 56.2 |
C7'—C12'—H12B | 120.0 | H33C—C33—H33D | 141.1 |
C4—C13—H13A | 109.5 | O5—C33—H33E | 109.5 |
C4—C13—H13B | 109.5 | H33A—C33—H33E | 141.1 |
H13A—C13—H13B | 109.5 | H33B—C33—H33E | 56.3 |
C4—C13—H13C | 109.5 | H33C—C33—H33E | 56.2 |
H13A—C13—H13C | 109.5 | H33D—C33—H33E | 109.5 |
H13B—C13—H13C | 109.5 | O5—C33—H33F | 109.5 |
O3—C14—O4 | 122.6 (3) | H33A—C33—H33F | 56.2 |
O3—C14—C5 | 122.1 (3) | H33B—C33—H33F | 141.1 |
O4—C14—C5 | 115.2 (3) | H33C—C33—H33F | 56.3 |
O4—C15—C16 | 106.7 (3) | H33D—C33—H33F | 109.5 |
O4—C15—H15A | 110.4 | H33E—C33—H33F | 109.5 |
C16—C15—H15A | 110.4 | N3—C34—H34A | 109.5 |
O4—C15—H15B | 110.4 | N3—C34—H34B | 109.5 |
C16—C15—H15B | 110.4 | H34A—C34—H34B | 109.5 |
H15A—C15—H15B | 108.6 | N3—C34—H34C | 109.5 |
C15—C16—H16A | 109.5 | H34A—C34—H34C | 109.5 |
C15—C16—H16B | 109.5 | H34B—C34—H34C | 109.5 |
C3—S1—C1—C2 | −6.90 (17) | C19—C1—C17—C18 | −6.1 (3) |
C3—S1—C1—C19 | −130.73 (17) | S1—C1—C17—C18 | 116.1 (2) |
C3—S1—C1—C17 | 110.61 (19) | C34—N3—C18—C17 | −172.2 (2) |
C3—N1—C2—O1 | 177.2 (2) | C19—N3—C18—C17 | −44.4 (3) |
C6—N1—C2—O1 | −13.8 (4) | C27—C17—C18—N3 | 158.5 (2) |
C3—N1—C2—C1 | −7.3 (3) | C1—C17—C18—N3 | 29.4 (3) |
C6—N1—C2—C1 | 161.6 (2) | C18—N3—C19—C26 | 170.7 (2) |
C19—C1—C2—O1 | −53.8 (3) | C34—N3—C19—C26 | −62.6 (3) |
C17—C1—C2—O1 | 61.3 (3) | C18—N3—C19—C20 | −77.1 (3) |
S1—C1—C2—O1 | −175.7 (2) | C34—N3—C19—C20 | 49.6 (3) |
C19—C1—C2—N1 | 130.9 (2) | C18—N3—C19—C1 | 39.3 (2) |
C17—C1—C2—N1 | −114.0 (2) | C34—N3—C19—C1 | 166.0 (2) |
S1—C1—C2—N1 | 9.0 (2) | C2—C1—C19—N3 | 97.7 (2) |
C4—N2—C3—N1 | 7.8 (4) | C17—C1—C19—N3 | −18.9 (2) |
C4—N2—C3—S1 | −169.03 (18) | S1—C1—C19—N3 | −143.92 (16) |
C2—N1—C3—N2 | −175.5 (2) | C2—C1—C19—C26 | −28.1 (3) |
C6—N1—C3—N2 | 15.3 (4) | C17—C1—C19—C26 | −144.8 (2) |
C2—N1—C3—S1 | 1.6 (3) | S1—C1—C19—C26 | 90.2 (2) |
C6—N1—C3—S1 | −167.60 (16) | C2—C1—C19—C20 | −144.8 (2) |
C1—S1—C3—N2 | −179.2 (2) | C17—C1—C19—C20 | 98.5 (2) |
C1—S1—C3—N1 | 3.57 (18) | S1—C1—C19—C20 | −26.5 (2) |
C3—N2—C4—C5 | −13.5 (4) | C21—N4—C20—O2 | 179.4 (2) |
C3—N2—C4—C13 | 165.1 (2) | C21—N4—C20—C19 | −2.3 (3) |
N2—C4—C5—C14 | 179.6 (2) | N3—C19—C20—O2 | 62.8 (3) |
C13—C4—C5—C14 | 1.3 (5) | C26—C19—C20—O2 | −178.3 (2) |
N2—C4—C5—C6 | −3.8 (4) | C1—C19—C20—O2 | −49.6 (3) |
C13—C4—C5—C6 | 177.8 (3) | N3—C19—C20—N4 | −115.5 (2) |
C3—N1—C6—C5 | −28.9 (3) | C26—C19—C20—N4 | 3.5 (3) |
C2—N1—C6—C5 | 162.6 (2) | C1—C19—C20—N4 | 132.1 (2) |
C3—N1—C6—C7 | 96.2 (3) | C20—N4—C21—C22 | 177.6 (3) |
C2—N1—C6—C7 | −72.4 (3) | C20—N4—C21—C26 | 0.0 (3) |
C4—C5—C6—N1 | 23.4 (3) | C26—C21—C22—C23 | −0.2 (4) |
C14—C5—C6—N1 | −159.6 (2) | N4—C21—C22—C23 | −177.5 (3) |
C4—C5—C6—C7 | −97.4 (3) | C21—C22—C23—C24 | 1.3 (5) |
C14—C5—C6—C7 | 79.7 (3) | C22—C23—C24—C25 | −0.6 (6) |
N1—C6—C7—C8 | −90.3 (3) | C23—C24—C25—C26 | −1.4 (5) |
C5—C6—C7—C8 | 30.2 (4) | C24—C25—C26—C21 | 2.5 (4) |
N1—C6—C7—C12 | 87.9 (3) | C24—C25—C26—C19 | 174.5 (3) |
C5—C6—C7—C12 | −151.6 (3) | C22—C21—C26—C25 | −1.7 (4) |
C12—C7—C8—C9 | 0.0 | N4—C21—C26—C25 | 176.0 (2) |
C6—C7—C8—C9 | 178.2 (3) | C22—C21—C26—C19 | −175.4 (3) |
C7—C8—C9—C10 | 0.0 | N4—C21—C26—C19 | 2.4 (3) |
C8—C9—C10—C11 | 0.0 | N3—C19—C26—C25 | −58.2 (4) |
C9—C10—C11—C12 | 0.0 | C20—C19—C26—C25 | −176.1 (3) |
C10—C11—C12—C7 | 0.0 | C1—C19—C26—C25 | 63.3 (4) |
C8—C7—C12—C11 | 0.0 | N3—C19—C26—C21 | 114.4 (2) |
C6—C7—C12—C11 | −178.2 (3) | C20—C19—C26—C21 | −3.4 (3) |
C12'—C7'—C8'—C9' | 0.0 | C1—C19—C26—C21 | −124.1 (2) |
C7'—C8'—C9'—C10' | 0.0 | C18—C17—C27—C32 | −48.3 (4) |
C8'—C9'—C10'—C11' | 0.0 | C1—C17—C27—C32 | 74.3 (3) |
C9'—C10'—C11'—C12' | 0.0 | C18—C17—C27—C28 | 133.1 (3) |
C10'—C11'—C12'—C7' | 0.0 | C1—C17—C27—C28 | −104.3 (3) |
C8'—C7'—C12'—C11' | 0.0 | C32—C27—C28—C29 | −0.7 (4) |
C15—O4—C14—O3 | 1.0 (5) | C17—C27—C28—C29 | 178.0 (3) |
C15—O4—C14—C5 | −179.3 (3) | C27—C28—C29—C30 | −0.6 (5) |
C4—C5—C14—O3 | −177.8 (3) | C28—C29—C30—C31 | 1.3 (5) |
C6—C5—C14—O3 | 5.3 (4) | C28—C29—C30—O5 | −179.2 (3) |
C4—C5—C14—O4 | 2.5 (4) | C33—O5—C30—C29 | 173.1 (3) |
C6—C5—C14—O4 | −174.4 (2) | C33—O5—C30—C31 | −7.4 (5) |
C14—O4—C15—C16 | 176.7 (3) | C29—C30—C31—C32 | −0.7 (5) |
C2—C1—C17—C27 | 103.2 (3) | O5—C30—C31—C32 | 179.8 (3) |
C19—C1—C17—C27 | −135.4 (2) | C28—C27—C32—C31 | 1.3 (4) |
S1—C1—C17—C27 | −13.1 (3) | C17—C27—C32—C31 | −177.3 (3) |
C2—C1—C17—C18 | −127.6 (2) | C30—C31—C32—C27 | −0.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2i | 0.86 | 2.31 | 3.027 (2) | 140 |
Symmetry code: (i) −x−1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C34H32N4O5S |
Mr | 608.70 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 14.990 (6), 11.375 (5), 17.815 (8) |
β (°) | 92.254 (6) |
V (Å3) | 3035 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.38 × 0.30 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.905, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14013, 6236, 3567 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.137, 1.00 |
No. of reflections | 6236 |
No. of parameters | 413 |
No. of restraints | 278 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.40 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2i | 0.86 | 2.31 | 3.027 (2) | 140 |
Symmetry code: (i) −x−1/2, y+1/2, −z+1/2. |
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Spiro-compounds represent an important class of naturally occurring substances, which in many cases exhibit important biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are widely used for the construction of spiro-compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported. The compound was synthesized by the intermolecular [3 + 2]-cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 2-(4-methoxy-benzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H- thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester (Tozkoparan, 1999).
The molecular structure of (I) is shown in Fig. 1. There exists a dispiro ring in the molecule that consists of a planar 2-oxindole ring, a pyrrolidine ring and a thiazolo[3,2-a]pyrimidine ring. The pyrrolidine ring (N3, C18, C17, C1 and C19) is not planar, and has an envelope conformation. Two molecules are connected by N—H···N hydrogen bonds, with an N···N distance of 3.027 (2) Å and an N—H···N angle 140.2°.