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In the title compound, C19H20N4O3S, three intra­molecular hydrogen bonds and π–π stacking are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016703/rn6051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016703/rn6051Isup2.hkl
Contains datablock I

CCDC reference: 277747

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.189
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Methyl 2-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylsulfanylmethyl)phenyl]- 3-methoxyacrylate top
Crystal data top
C19H20N4O3SZ = 2
Mr = 384.45F(000) = 404
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P1Melting point: 455 K
a = 8.9163 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5613 (13) ÅCell parameters from 1142 reflections
c = 12.0628 (17) Åθ = 2.3–21.1°
α = 102.881 (3)°µ = 0.20 mm1
β = 90.646 (3)°T = 292 K
γ = 109.411 (3)°Plate, yellow
V = 941.4 (2) Å30.30 × 0.20 × 0.04 mm
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
φ and ω scansh = 107
4766 measured reflectionsk = 1111
3261 independent reflectionsl = 1414
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0954P)2]
where P = (Fo2 + 2Fc2)/3
3261 reflections(Δ/σ)max = 0.031
248 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.63 e Å3
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
C10.2630 (4)0.0772 (4)0.6083 (3)0.0518 (9)
C20.1207 (4)0.2049 (4)0.5785 (3)0.0516 (9)
H20.09110.27240.62570.062*
C30.0265 (4)0.2304 (4)0.4817 (3)0.0461 (8)
C40.3677 (5)0.0500 (5)0.7149 (4)0.0786 (13)
H4A0.44540.09930.69760.118*
H4B0.30340.09120.77120.118*
H4C0.42130.05780.74420.118*
C50.1238 (4)0.3603 (4)0.4387 (3)0.0613 (10)
H5A0.10850.42310.36880.092*
H5B0.20730.32200.42490.092*
H5C0.15290.41990.49450.092*
C60.2209 (4)0.0020 (4)0.4493 (3)0.0435 (8)
C70.1149 (4)0.0016 (4)0.2947 (3)0.0464 (8)
C80.2661 (4)0.1980 (4)0.1639 (3)0.0510 (9)
H8A0.34970.16960.19470.061*
H8B0.28150.19630.08420.061*
C90.2856 (4)0.3587 (4)0.2264 (3)0.0399 (8)
C100.3945 (4)0.4305 (4)0.3228 (3)0.0511 (9)
H100.45060.37660.34970.061*
C110.4204 (4)0.5788 (4)0.3787 (3)0.0526 (9)
H110.49600.62560.44150.063*
C120.3345 (4)0.6589 (4)0.3422 (3)0.0497 (9)
H120.35040.75910.38100.060*
C130.2240 (4)0.5890 (4)0.2470 (3)0.0456 (8)
H130.16570.64290.22270.055*
C140.1994 (4)0.4406 (3)0.1880 (2)0.0376 (7)
C150.0873 (4)0.3711 (3)0.0812 (3)0.0383 (7)
C160.1411 (4)0.3504 (4)0.0213 (3)0.0449 (8)
H160.06890.31060.08620.054*
C170.3441 (5)0.3714 (5)0.1472 (3)0.0688 (12)
H17A0.29510.26750.18990.103*
H17B0.45820.39950.14510.103*
H17C0.31030.43730.18300.103*
C180.0851 (4)0.3334 (4)0.0928 (3)0.0454 (8)
C190.3433 (4)0.2186 (5)0.0054 (4)0.0757 (13)
H19A0.37650.16170.05170.114*
H19B0.39430.15630.07880.114*
H19C0.37290.30830.01240.114*
N10.3137 (4)0.0228 (3)0.5445 (3)0.0522 (8)
N20.0802 (3)0.1248 (3)0.4185 (2)0.0420 (7)
N30.0103 (3)0.1231 (3)0.3172 (2)0.0478 (7)
N40.2438 (3)0.0792 (3)0.3701 (2)0.0487 (7)
O10.1426 (3)0.3613 (3)0.1807 (2)0.0639 (7)
O20.1725 (3)0.2627 (3)0.0075 (2)0.0615 (7)
O30.2975 (3)0.3861 (3)0.03263 (19)0.0540 (7)
S10.07418 (12)0.05487 (10)0.17149 (8)0.0570 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.053 (2)0.050 (2)0.0204 (18)0.0020 (17)0.0133 (17)
C20.057 (2)0.048 (2)0.053 (2)0.0178 (18)0.0114 (18)0.0190 (17)
C30.045 (2)0.0400 (18)0.054 (2)0.0140 (16)0.0155 (16)0.0129 (15)
C40.072 (3)0.090 (3)0.070 (3)0.014 (2)0.013 (2)0.033 (2)
C50.061 (3)0.046 (2)0.064 (2)0.0008 (18)0.010 (2)0.0153 (18)
C60.0394 (19)0.0377 (18)0.053 (2)0.0121 (15)0.0031 (16)0.0125 (15)
C70.045 (2)0.0357 (18)0.058 (2)0.0145 (16)0.0009 (17)0.0102 (15)
C80.062 (2)0.050 (2)0.049 (2)0.0252 (18)0.0101 (17)0.0199 (16)
C90.0418 (19)0.0439 (18)0.0353 (17)0.0124 (15)0.0063 (14)0.0153 (14)
C100.046 (2)0.066 (2)0.049 (2)0.0197 (18)0.0060 (17)0.0283 (18)
C110.044 (2)0.064 (2)0.0378 (19)0.0044 (18)0.0015 (15)0.0101 (17)
C120.050 (2)0.048 (2)0.0407 (19)0.0074 (17)0.0045 (16)0.0031 (15)
C130.044 (2)0.0459 (19)0.0455 (19)0.0139 (16)0.0031 (15)0.0119 (15)
C140.0367 (18)0.0419 (18)0.0348 (17)0.0125 (14)0.0044 (13)0.0117 (14)
C150.0397 (18)0.0366 (17)0.0379 (18)0.0105 (14)0.0010 (14)0.0112 (13)
C160.042 (2)0.0428 (19)0.046 (2)0.0087 (15)0.0045 (16)0.0116 (15)
C170.059 (3)0.095 (3)0.047 (2)0.018 (2)0.0111 (19)0.017 (2)
C180.046 (2)0.0386 (18)0.050 (2)0.0116 (16)0.0053 (17)0.0117 (16)
C190.039 (2)0.084 (3)0.090 (3)0.004 (2)0.010 (2)0.019 (3)
N10.0475 (18)0.0481 (17)0.0575 (19)0.0118 (14)0.0035 (15)0.0132 (14)
N20.0398 (16)0.0356 (15)0.0486 (16)0.0105 (12)0.0035 (13)0.0099 (12)
N30.0488 (17)0.0385 (16)0.0544 (18)0.0120 (13)0.0017 (14)0.0127 (13)
N40.0488 (18)0.0396 (16)0.0568 (18)0.0098 (13)0.0003 (14)0.0181 (13)
O10.0472 (16)0.083 (2)0.0551 (17)0.0168 (14)0.0094 (13)0.0119 (14)
O20.0422 (15)0.0732 (18)0.0570 (16)0.0089 (13)0.0084 (12)0.0087 (13)
O30.0428 (15)0.0773 (18)0.0383 (13)0.0144 (13)0.0054 (11)0.0159 (12)
S10.0661 (7)0.0423 (5)0.0593 (6)0.0130 (5)0.0117 (5)0.0150 (4)
Geometric parameters (Å, º) top
C1—N11.327 (5)C10—C111.367 (5)
C1—C21.412 (5)C10—H100.9300
C1—C41.502 (5)C11—C121.379 (5)
C2—C31.357 (5)C11—H110.9300
C2—H20.9300C12—C131.389 (4)
C3—N21.364 (4)C12—H120.9300
C3—C51.483 (5)C13—C141.381 (4)
C4—H4A0.9600C13—H130.9300
C4—H4B0.9600C14—C151.499 (4)
C4—H4C0.9600C15—C161.329 (4)
C5—H5A0.9600C15—C181.473 (5)
C5—H5B0.9600C16—O31.337 (4)
C5—H5C0.9600C16—H160.9300
C6—N41.336 (4)C17—O31.438 (4)
C6—N11.337 (4)C17—H17A0.9600
C6—N21.381 (4)C17—H17B0.9600
C7—N31.333 (4)C17—H17C0.9600
C7—N41.344 (4)C18—O11.198 (4)
C7—S11.746 (3)C18—O21.340 (4)
C8—C91.504 (4)C19—O21.441 (4)
C8—S11.820 (4)C19—H19A0.9600
C8—H8A0.9700C19—H19B0.9600
C8—H8B0.9700C19—H19C0.9600
C9—C101.394 (4)N2—N31.371 (4)
C9—C141.403 (4)
N1—C1—C2122.9 (3)C12—C11—H11120.0
N1—C1—C4116.3 (3)C11—C12—C13119.5 (3)
C2—C1—C4120.7 (3)C11—C12—H12120.2
C3—C2—C1120.9 (3)C13—C12—H12120.2
C3—C2—H2119.6C14—C13—C12121.0 (3)
C1—C2—H2119.6C14—C13—H13119.5
C2—C3—N2115.0 (3)C12—C13—H13119.5
C2—C3—C5126.8 (3)C13—C14—C9119.2 (3)
N2—C3—C5118.2 (3)C13—C14—C15120.0 (3)
C1—C4—H4A109.5C9—C14—C15120.7 (3)
C1—C4—H4B109.5C16—C15—C18120.6 (3)
H4A—C4—H4B109.5C16—C15—C14121.4 (3)
C1—C4—H4C109.5C18—C15—C14117.9 (3)
H4A—C4—H4C109.5C15—C16—O3121.0 (3)
H4B—C4—H4C109.5C15—C16—H16119.5
C3—C5—H5A109.5O3—C16—H16119.5
C3—C5—H5B109.5O3—C17—H17A109.5
H5A—C5—H5B109.5O3—C17—H17B109.5
C3—C5—H5C109.5H17A—C17—H17B109.5
H5A—C5—H5C109.5O3—C17—H17C109.5
H5B—C5—H5C109.5H17A—C17—H17C109.5
N4—C6—N1128.6 (3)H17B—C17—H17C109.5
N4—C6—N2109.2 (3)O1—C18—O2123.1 (3)
N1—C6—N2122.1 (3)O1—C18—C15124.9 (3)
N3—C7—N4117.3 (3)O2—C18—C15112.0 (3)
N3—C7—S1118.2 (3)O2—C19—H19A109.5
N4—C7—S1124.5 (3)O2—C19—H19B109.5
C9—C8—S1115.2 (2)H19A—C19—H19B109.5
C9—C8—H8A108.5O2—C19—H19C109.5
S1—C8—H8A108.5H19A—C19—H19C109.5
C9—C8—H8B108.5H19B—C19—H19C109.5
S1—C8—H8B108.5C1—N1—C6116.3 (3)
H8A—C8—H8B107.5C3—N2—N3127.4 (3)
C10—C9—C14118.8 (3)C3—N2—C6122.8 (3)
C10—C9—C8119.8 (3)N3—N2—C6109.8 (3)
C14—C9—C8121.5 (3)C7—N3—N2101.0 (3)
C11—C10—C9121.3 (3)C6—N4—C7102.7 (3)
C11—C10—H10119.3C18—O2—C19116.4 (3)
C9—C10—H10119.3C16—O3—C17116.6 (3)
C10—C11—C12120.1 (3)C7—S1—C8100.51 (16)
C10—C11—H11120.0
N1—C1—C2—C30.8 (6)C2—C1—N1—C60.9 (5)
C4—C1—C2—C3179.5 (4)C4—C1—N1—C6179.6 (3)
C1—C2—C3—N20.0 (5)N4—C6—N1—C1179.4 (3)
C1—C2—C3—C5178.8 (3)N2—C6—N1—C10.1 (5)
S1—C8—C9—C10112.5 (3)C2—C3—N2—N3179.3 (3)
S1—C8—C9—C1469.2 (4)C5—C3—N2—N30.3 (5)
C14—C9—C10—C111.2 (5)C2—C3—N2—C60.8 (5)
C8—C9—C10—C11177.1 (3)C5—C3—N2—C6178.2 (3)
C9—C10—C11—C122.0 (5)N4—C6—N2—C3178.7 (3)
C10—C11—C12—C131.3 (5)N1—C6—N2—C30.8 (5)
C11—C12—C13—C140.4 (5)N4—C6—N2—N30.1 (4)
C12—C13—C14—C91.2 (5)N1—C6—N2—N3179.5 (3)
C12—C13—C14—C15176.0 (3)N4—C7—N3—N20.2 (4)
C10—C9—C14—C130.4 (5)S1—C7—N3—N2178.7 (2)
C8—C9—C14—C13178.7 (3)C3—N2—N3—C7178.8 (3)
C10—C9—C14—C15176.8 (3)C6—N2—N3—C70.1 (3)
C8—C9—C14—C151.5 (5)N1—C6—N4—C7179.6 (4)
C13—C14—C15—C16105.7 (4)N2—C6—N4—C70.2 (4)
C9—C14—C15—C1671.5 (4)N3—C7—N4—C60.3 (4)
C13—C14—C15—C1871.2 (4)S1—C7—N4—C6178.6 (3)
C9—C14—C15—C18111.6 (3)O1—C18—O2—C190.8 (5)
C18—C15—C16—O3179.2 (3)C15—C18—O2—C19179.1 (3)
C14—C15—C16—O32.4 (5)C15—C16—O3—C17175.0 (3)
C16—C15—C18—O1172.8 (3)N3—C7—S1—C8167.8 (3)
C14—C15—C18—O14.1 (5)N4—C7—S1—C813.3 (3)
C16—C15—C18—O27.4 (4)C9—C8—S1—C789.5 (3)
C14—C15—C18—O2175.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O20.932.312.658 (4)102
C8—H8B···O30.972.503.242 (4)133
C8—H8A···N40.972.542.939 (4)105
 

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