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Comparison of the title compound, C20H28N2O5S, with related structures shows that the presence of the alkyl substituents influences the conformation of the rings in the frame fragment. The mol­ecules form hydrogen-bonded centrosymmetric dimers due to an N—H...S inter­molecular inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061247/bg2144sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061247/bg2144Isup2.hkl
Contains datablock I

CCDC reference: 673086

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.066
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O5 - C18 .. 12.21 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.89 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C9 .. 6.52 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C14 .. 6.02 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C16 .. 6.34 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C10 .. 5.69 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 .. 6.57 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O5
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C1 ..... R PLAT793_ALERT_1_G Check the Absolute Configuration of C8 ..... R PLAT793_ALERT_1_G Check the Absolute Configuration of C10 ..... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: All authors made significant contribution in this work. The idea of synthesis belong to Kovalenko S. M. and Chernykh. The synthesis was performed by Zaremba and Kovalenko S. S.. X-ray diffraction experiment was performed by Baumer. The analysis of diffraction data was performed by Konovalova and Shishkin.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Some derivatives of 2,6-methano-2H-1,3,5-benzothiadiazocine and -benzoxadiazocine have been studied due to their biological activity as perspective calcium channel blockers (Baldwin et al., 1986; Kettmann et al., 1996; Kettmann & Svetlík, 1996, 1997). We have performed an X-ray diffraction study of a new member of this group, the title compound C20H28N2O5S1 (I). Tetrahydropyrimidine-2-thione and tetrahydropyran rings adopt in (I) a conformation which is intermediate between half-chair and sofa. Maximum deviations from the tetrahydropyrimidine and the tetrahydropyrane mean planes correspond to atoms C1, C10 (0.28 A°, -0.54 A°) and C8,C10 (0.21 A°, -0.59 A°), respectively. Comparison of the ring conformations in (I) and some of its analogues (Kettmann et al., 1996b; Fu et al., 2002; Kettmann et al., 1997) indicates that the presence of substituent at the nitrogen atoms is probably the reason for some deformation in the heterocycles conformation. The ester substituent in (I) is planar within 0.01 A° and coplanar to the C8—C10 bond (the C8—C10—C11—O2 torsion angle is 2.2 (3) °). The methoxybuthyl substituent adopts instead an orthogonal orientation with respect to the tetrahydropyrimidine ring (the C9—N2—C16—C17 torsion angle is -92.7 (2) °) probably due to the repulsion between some of its atoms and the tione and the methyl groups (as sugested by the short intramolecular contacts C20···H16A 2.43 Å (van der Waals radii sum is 2.87 Å, Zefirov & Zorky, 1995), H16A···H20C 2.12 Å [2.32 Å], S1···H16B is 2.53 Å [3.01 Å]). The ethoxy substituent is turned with respect to the plane of the aromatic ring (the C5—C6—O4—C14 torsion angle is 17.6 (3) °) probably due to the repulsion between atoms of these fragments (shortened intramolecular contacts C14···H5 2.59 Å [van der Waals radii sum is 2.87 Å], C5···H14A 2.71 Å [2.87 Å]). In the crystal phase the molecules of (I) form centrosymmetric dimers due to a weak intermolecular hydrogen bond (Table 1).

Related literature top

For related literature, see: Baldwin et al. (1986); Biginelli, (1893); Fu et al. (2002); Kettmann & Svetlík (1996, 1997); Kettmann et al. (1996); Zefirov & Zorky (1995).

Experimental top

The synthesis was carried out according to the Biginelli reaction (Biginelli, 1893). 2-Hydroxy-3-etoxysalicylic aldehyde (0,01 mol), N-(3-methoxypropyl)-thiourea and ethyl acetoacetate (0,015 mol) were mixed in 10 ml of ethanol. 3 drops of concentrated HCL were added. Raw crystals of the title compound were grown during 2 days at room temperature; they were further filtered, washed in ethanol and dried at room temperature. Crystals apt for X-ray diffraction were obtained by quick evaporation of a solution of (I) in dimethylformamide.

Refinement top

All hydrogen atoms were located from electron density difference maps, idealized and included in the refinement in the riding approximation with Uiso constrained to be 1.5 times Ueq of the carrier atom for the methyl groups and 1.2 times Ueq of the carrier atom for the other atoms.

Computing details top

Data collection: P3 (Siemens,1989); cell refinement: P3 (Siemens,1989); data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: XP (Siemens, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound with atomic numbering. Displacement ellipsoids drawn at the 50% probability level.
Ethyl 6-ethoxy-10-(3-methoxypropyl)-9-methyl-11-thioxo-8-oxa-10,12- diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylate top
Crystal data top
C20H28N2O5SZ = 2
Mr = 408.50F(000) = 436
Triclinic, P1Dx = 1.277 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7612 (16) ÅCell parameters from 36 reflections
b = 10.3405 (17) Åθ = 8–22°
c = 12.309 (2) ŵ = 0.19 mm1
α = 107.354 (13)°T = 293 K
β = 109.709 (13)°Block, colourless
γ = 100.096 (12)°0.40 × 0.20 × 0.20 mm
V = 1062.5 (4) Å3
Data collection top
Siemens P3/PC
diffractometer
2151 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
Detector resolution: 16.1827 pixels mm-1h = 1110
θ/2θ scansk = 1211
3927 measured reflectionsl = 014
3737 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.066H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.0177P)2]
where P = (Fo2 + 2Fc2)/3
3737 reflections(Δ/σ)max = 0.001
257 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.12 e Å3
Crystal data top
C20H28N2O5Sγ = 100.096 (12)°
Mr = 408.50V = 1062.5 (4) Å3
Triclinic, P1Z = 2
a = 9.7612 (16) ÅMo Kα radiation
b = 10.3405 (17) ŵ = 0.19 mm1
c = 12.309 (2) ÅT = 293 K
α = 107.354 (13)°0.40 × 0.20 × 0.20 mm
β = 109.709 (13)°
Data collection top
Siemens P3/PC
diffractometer
2151 reflections with I > 2σ(I)
3927 measured reflectionsRint = 0.053
3737 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 0.89Δρmax = 0.19 e Å3
3737 reflectionsΔρmin = 0.12 e Å3
257 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.33397 (6)0.30050 (6)0.46821 (5)0.05561 (17)
C10.51711 (19)0.33456 (17)0.22987 (15)0.0366 (4)
H10.54960.42210.21720.044*
C20.64837 (19)0.27649 (17)0.26528 (15)0.0360 (4)
C30.8001 (2)0.36494 (19)0.33397 (16)0.0447 (5)
H30.82200.46300.35760.054*
C40.9156 (2)0.3074 (2)0.36622 (18)0.0559 (6)
H41.01600.36690.41100.067*
C50.8859 (2)0.1622 (2)0.33345 (18)0.0560 (6)
H50.96590.12460.35670.067*
C60.7364 (2)0.0724 (2)0.26571 (17)0.0471 (5)
C70.61870 (19)0.13107 (18)0.23001 (16)0.0365 (4)
O10.47460 (13)0.03496 (12)0.15539 (11)0.0435 (3)
C80.34663 (19)0.09174 (18)0.13639 (16)0.0404 (5)
N20.31829 (16)0.12553 (14)0.25062 (13)0.0401 (4)
C90.37102 (19)0.25931 (18)0.33937 (16)0.0384 (4)
N10.45580 (16)0.36240 (14)0.32376 (13)0.0405 (4)
H1N0.47500.44930.37150.049*
C100.38594 (19)0.22459 (17)0.11061 (16)0.0382 (4)
H100.42300.20220.04460.046*
C110.2556 (2)0.2852 (2)0.07013 (18)0.0513 (5)
O20.12758 (17)0.24063 (17)0.06021 (17)0.0882 (5)
O30.30182 (15)0.39880 (15)0.04911 (12)0.0590 (4)
C120.1892 (3)0.4702 (3)0.0106 (2)0.0770 (7)
H12A0.15080.50060.07400.115*
H12B0.10380.40570.06710.115*
C130.2648 (3)0.5951 (3)0.0066 (3)0.1075 (10)
H13A0.34450.66140.07210.161*
H13B0.19100.64030.03750.161*
H13C0.30810.56450.06560.161*
O40.69411 (16)0.07243 (14)0.22771 (13)0.0640 (4)
C140.7999 (3)0.1341 (3)0.2869 (3)0.1045 (10)
H14A0.84630.08100.37670.157*
H14B0.88030.13130.25730.157*
C150.7188 (4)0.2819 (3)0.2576 (2)0.1044 (10)
H15A0.64650.28340.29460.157*
H15B0.79090.32750.29060.157*
H15C0.66580.33160.16860.157*
C160.2414 (2)0.0061 (2)0.27311 (19)0.0579 (6)
H16A0.16180.06350.19440.087*
H16B0.19330.04140.32820.087*
C170.3498 (3)0.0645 (3)0.3302 (2)0.0807 (7)
H17A0.43960.00820.39920.121*
H17B0.38250.11530.26840.121*
C180.2826 (3)0.1691 (3)0.3784 (3)0.0983 (9)
H18A0.36370.19590.42910.148*
H18B0.23530.12360.43040.148*
O50.17768 (19)0.28630 (17)0.28194 (14)0.0856 (5)
C190.1400 (4)0.3987 (3)0.3224 (3)0.1141 (11)
H19A0.23110.42010.36240.171*
H19B0.06840.48190.25140.171*
H19C0.09540.36920.38050.171*
C200.2177 (2)0.02969 (19)0.02500 (17)0.0551 (6)
H20A0.23270.03660.04950.083*
H20B0.12200.01220.01660.083*
H20C0.21680.11720.03730.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0581 (3)0.0510 (3)0.0540 (3)0.0063 (3)0.0338 (3)0.0092 (3)
C10.0397 (11)0.0283 (9)0.0453 (11)0.0049 (8)0.0210 (9)0.0179 (9)
C20.0405 (11)0.0346 (10)0.0368 (10)0.0070 (9)0.0215 (9)0.0151 (8)
C30.0422 (12)0.0348 (10)0.0487 (12)0.0044 (9)0.0149 (10)0.0137 (9)
C40.0366 (12)0.0634 (15)0.0571 (14)0.0079 (11)0.0116 (10)0.0225 (11)
C50.0446 (13)0.0622 (14)0.0630 (14)0.0221 (11)0.0191 (11)0.0268 (11)
C60.0553 (13)0.0416 (12)0.0527 (13)0.0192 (11)0.0271 (11)0.0211 (10)
C70.0349 (10)0.0351 (10)0.0399 (11)0.0082 (9)0.0162 (9)0.0153 (9)
O10.0399 (8)0.0322 (7)0.0547 (8)0.0098 (6)0.0201 (6)0.0120 (6)
C80.0342 (11)0.0348 (10)0.0453 (12)0.0045 (9)0.0151 (9)0.0113 (9)
N20.0434 (9)0.0289 (8)0.0488 (9)0.0050 (7)0.0250 (8)0.0131 (7)
C90.0329 (10)0.0321 (10)0.0455 (11)0.0074 (8)0.0140 (9)0.0129 (9)
N10.0485 (10)0.0244 (8)0.0482 (10)0.0090 (7)0.0260 (8)0.0082 (7)
C100.0358 (10)0.0355 (10)0.0365 (11)0.0043 (8)0.0128 (9)0.0115 (8)
C110.0490 (14)0.0498 (13)0.0529 (13)0.0130 (11)0.0176 (11)0.0222 (10)
O20.0411 (9)0.0877 (12)0.1408 (16)0.0196 (8)0.0280 (10)0.0619 (11)
O30.0648 (9)0.0600 (9)0.0669 (10)0.0277 (8)0.0284 (8)0.0378 (8)
C120.102 (2)0.0726 (17)0.0708 (16)0.0537 (16)0.0323 (15)0.0360 (14)
C130.141 (3)0.0629 (18)0.111 (2)0.0521 (18)0.035 (2)0.0318 (17)
O40.0663 (10)0.0432 (9)0.0851 (11)0.0258 (7)0.0271 (8)0.0281 (8)
C140.118 (2)0.0620 (18)0.132 (2)0.0471 (17)0.032 (2)0.0467 (17)
C150.164 (3)0.0660 (18)0.110 (2)0.0559 (18)0.068 (2)0.0463 (16)
C160.0695 (15)0.0403 (12)0.0606 (14)0.0024 (11)0.0344 (12)0.0147 (10)
C170.0720 (16)0.0715 (16)0.0985 (19)0.0092 (14)0.0266 (15)0.0502 (15)
C180.109 (2)0.0844 (19)0.095 (2)0.0057 (17)0.0273 (18)0.0573 (17)
O50.1038 (13)0.0639 (11)0.0701 (11)0.0084 (10)0.0246 (10)0.0334 (9)
C190.164 (3)0.0719 (18)0.115 (2)0.0061 (19)0.063 (2)0.0579 (17)
C200.0458 (12)0.0484 (13)0.0493 (12)0.0006 (10)0.0119 (10)0.0067 (10)
Geometric parameters (Å, º) top
S1—C91.6927 (18)C12—C131.481 (3)
C1—N11.451 (2)C12—H12A0.9700
C1—C21.497 (2)C12—H12B0.9700
C1—C101.521 (2)C13—H13A0.9600
C1—H10.9800C13—H13B0.9600
C2—C71.381 (2)C13—H13C0.9600
C2—C31.401 (2)O4—C141.416 (3)
C3—C41.362 (3)C14—C151.466 (3)
C3—H30.9300C14—H14A0.9700
C4—C51.382 (3)C14—H14B0.9700
C4—H40.9300C15—H15A0.9600
C5—C61.389 (3)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—O41.367 (2)C16—C171.490 (3)
C6—C71.394 (2)C16—H16A0.9700
C7—O11.3798 (19)C16—H16B0.9700
O1—C81.450 (2)C17—C181.532 (3)
C8—N21.476 (2)C17—H17A0.9700
C8—C101.514 (2)C17—H17B0.9700
C8—C201.515 (2)C18—O51.346 (3)
N2—C91.357 (2)C18—H18A0.9700
N2—C161.478 (2)C18—H18B0.9700
C9—N11.334 (2)O5—C191.432 (2)
N1—H1N0.8600C19—H19A0.9600
C10—C111.516 (3)C19—H19B0.9600
C10—H100.9800C19—H19C0.9600
C11—O21.204 (2)C20—H20A0.9600
C11—O31.313 (2)C20—H20B0.9600
O3—C121.456 (2)C20—H20C0.9600
N1—C1—C2111.76 (14)O3—C12—H12B110.1
N1—C1—C10105.55 (13)C13—C12—H12B110.1
C2—C1—C10109.75 (14)H12A—C12—H12B108.4
N1—C1—H1109.9C12—C13—H13A109.5
C2—C1—H1109.9C12—C13—H13B109.5
C10—C1—H1109.9H13A—C13—H13B109.5
C7—C2—C3118.97 (17)C12—C13—H13C109.5
C7—C2—C1118.86 (15)H13A—C13—H13C109.5
C3—C2—C1122.17 (16)H13B—C13—H13C109.5
C4—C3—C2120.08 (18)C6—O4—C14118.18 (17)
C4—C3—H3120.0O4—C14—C15108.7 (2)
C2—C3—H3120.0O4—C14—H14A109.9
C3—C4—C5121.07 (19)C15—C14—H14A109.9
C3—C4—H4119.5O4—C14—H14B109.9
C5—C4—H4119.5C15—C14—H14B109.9
C4—C5—C6119.90 (19)H14A—C14—H14B108.3
C4—C5—H5120.1C14—C15—H15A109.5
C6—C5—H5120.1C14—C15—H15B109.5
O4—C6—C5124.83 (18)H15A—C15—H15B109.5
O4—C6—C7116.18 (17)C14—C15—H15C109.5
C5—C6—C7118.97 (18)H15A—C15—H15C109.5
O1—C7—C2123.19 (16)H15B—C15—H15C109.5
O1—C7—C6115.82 (15)N2—C16—C17112.23 (17)
C2—C7—C6120.96 (16)N2—C16—H16A109.2
C7—O1—C8117.03 (13)C17—C16—H16A109.2
O1—C8—N2108.40 (14)N2—C16—H16B109.2
O1—C8—C10108.89 (13)C17—C16—H16B109.2
N2—C8—C10110.53 (14)H16A—C16—H16B107.9
O1—C8—C20102.78 (14)C16—C17—C18114.0 (2)
N2—C8—C20112.72 (15)C16—C17—H17A108.8
C10—C8—C20113.09 (15)C18—C17—H17A108.8
C9—N2—C8122.51 (14)C16—C17—H17B108.8
C9—N2—C16119.32 (15)C18—C17—H17B108.8
C8—N2—C16117.94 (14)H17A—C17—H17B107.7
N1—C9—N2118.16 (16)O5—C18—C17110.4 (2)
N1—C9—S1118.88 (13)O5—C18—H18A109.6
N2—C9—S1122.96 (13)C17—C18—H18A109.6
C9—N1—C1122.96 (14)O5—C18—H18B109.6
C9—N1—H1N118.5C17—C18—H18B109.6
C1—N1—H1N118.5H18A—C18—H18B108.1
C8—C10—C11115.46 (15)C18—O5—C19111.30 (18)
C8—C10—C1106.56 (14)O5—C19—H19A109.5
C11—C10—C1110.17 (14)O5—C19—H19B109.5
C8—C10—H10108.1H19A—C19—H19B109.5
C11—C10—H10108.1O5—C19—H19C109.5
C1—C10—H10108.1H19A—C19—H19C109.5
O2—C11—O3123.1 (2)H19B—C19—H19C109.5
O2—C11—C10126.59 (19)C8—C20—H20A109.5
O3—C11—C10110.29 (17)C8—C20—H20B109.5
C11—O3—C12116.75 (17)H20A—C20—H20B109.5
O3—C12—C13108.0 (2)C8—C20—H20C109.5
O3—C12—H12A110.1H20A—C20—H20C109.5
C13—C12—H12A110.1H20B—C20—H20C109.5
N1—C1—C2—C788.77 (18)C8—N2—C9—S1177.75 (13)
C10—C1—C2—C728.0 (2)C16—N2—C9—S17.9 (2)
N1—C1—C2—C390.64 (19)N2—C9—N1—C111.6 (2)
C10—C1—C2—C3152.62 (16)S1—C9—N1—C1168.40 (12)
C7—C2—C3—C40.7 (3)C2—C1—N1—C974.0 (2)
C1—C2—C3—C4178.67 (16)C10—C1—N1—C945.3 (2)
C2—C3—C4—C50.7 (3)O1—C8—C10—C11171.51 (14)
C3—C4—C5—C60.5 (3)N2—C8—C10—C1169.51 (19)
C4—C5—C6—O4179.55 (18)C20—C8—C10—C1157.9 (2)
C4—C5—C6—C71.2 (3)O1—C8—C10—C165.80 (17)
C3—C2—C7—O1175.56 (15)N2—C8—C10—C153.17 (18)
C1—C2—C7—O15.0 (2)C20—C8—C10—C1179.38 (15)
C3—C2—C7—C62.4 (2)N1—C1—C10—C863.55 (17)
C1—C2—C7—C6177.02 (16)C2—C1—C10—C857.03 (17)
O4—C6—C7—O13.0 (2)N1—C1—C10—C1162.40 (18)
C5—C6—C7—O1175.50 (16)C2—C1—C10—C11177.02 (15)
O4—C6—C7—C2178.85 (15)C8—C10—C11—O22.2 (3)
C5—C6—C7—C22.6 (3)C1—C10—C11—O2118.6 (2)
C2—C7—O1—C813.4 (2)C8—C10—C11—O3179.32 (15)
C6—C7—O1—C8168.57 (15)C1—C10—C11—O359.9 (2)
C7—O1—C8—N276.22 (17)O2—C11—O3—C120.8 (3)
C7—O1—C8—C1044.07 (19)C10—C11—O3—C12179.37 (15)
C7—O1—C8—C20164.25 (14)C11—O3—C12—C13179.40 (18)
O1—C8—N2—C998.62 (17)C5—C6—O4—C1417.6 (3)
C10—C8—N2—C920.7 (2)C7—C6—O4—C14164.0 (2)
C20—C8—N2—C9148.30 (16)C6—O4—C14—C15164.75 (18)
O1—C8—N2—C1675.83 (18)C9—N2—C16—C1792.7 (2)
C10—C8—N2—C16164.90 (15)C8—N2—C16—C1781.9 (2)
C20—C8—N2—C1637.2 (2)N2—C16—C17—C18168.78 (19)
C8—N2—C9—N12.3 (2)C16—C17—C18—O570.9 (3)
C16—N2—C9—N1172.10 (16)C17—C18—O5—C19166.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.862.623.3973 (17)152
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC20H28N2O5S
Mr408.50
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.7612 (16), 10.3405 (17), 12.309 (2)
α, β, γ (°)107.354 (13), 109.709 (13), 100.096 (12)
V3)1062.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerSiemens P3/PC
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3927, 3737, 2151
Rint0.053
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.066, 0.89
No. of reflections3737
No. of parameters257
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.12

Computer programs: P3 (Siemens,1989), XDISK (Siemens, 1991), SHELXTL (Sheldrick, 1998), XP (Siemens, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.862.623.3973 (17)151.6
Symmetry code: (i) x+1, y+1, z+1.
 

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