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The title compound, C19H18N2O4S, was synthesized by the reaction of methyl (2-hydroxy­phenyl)­acetate and 3-(4-methyl­thio)­phenyl-5-chloro­methyl-1,2,4-oxa­diazo­le. The structure exhibits intermolecular C—H...O hydrogen bonds and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026649/fl6129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026649/fl6129Isup2.hkl
Contains datablock I

CCDC reference: 255936

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.142
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT733_ALERT_1_A Torsion Calc -178.90(16), Rep -179(3) ...... 9.90 su-Rat O2 -C11 -C16 -C15 1.555 1.555 1.555 1.555
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B .. CG3 .. 2.85 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C19 H18 N2 O4 S
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Methyl 2-{[3-(4-methylsulfanyl)phenyl-1,2,4-oxadiazol- 5-yl]methoxy}phenylacetate top
Crystal data top
C19H18N2O4SZ = 2
Mr = 370.41F(000) = 388
Triclinic, P1Dx = 1.373 Mg m3
a = 8.3580 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.522 (2) ÅCell parameters from 25 reflections
c = 10.581 (2) Åθ = 10–13°
α = 90.13 (3)°µ = 0.21 mm1
β = 102.08 (3)°T = 293 K
γ = 99.73 (3)°Block, colourless
V = 896.1 (3) Å30.4 × 0.3 × 0.3 mm
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.0°
Graphite monochromatorh = 010
ω/2θ scansk = 1212
3752 measured reflectionsl = 1312
3499 independent reflections3 standard reflections every 200 reflections
2763 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.1P)2 + 0.35P]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.014
3499 reflectionsΔρmax = 0.32 e Å3
236 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (5)
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
S0.10592 (7)0.01231 (6)0.85337 (7)0.0594 (2)
O10.84214 (18)0.42310 (16)1.09084 (14)0.0513 (4)
N20.6154 (2)0.41523 (16)1.16328 (15)0.0406 (4)
O40.60500 (19)0.87935 (14)1.60436 (19)0.0610 (5)
O30.84235 (17)0.74158 (15)1.66992 (18)0.0590 (5)
O20.73315 (17)0.57758 (13)1.37455 (13)0.0406 (3)
N10.7524 (2)0.3417 (2)1.00828 (18)0.0538 (5)
C10.1752 (3)0.0760 (3)0.7257 (3)0.0715 (8)
H1B0.09880.13250.69210.107*
H1C0.18070.01710.65800.107*
H1D0.28340.12610.75820.107*
C20.2567 (3)0.1099 (2)0.9043 (2)0.0444 (5)
C30.4027 (3)0.1014 (2)0.8583 (2)0.0559 (6)
H3A0.42190.04400.79420.067*
C40.5187 (3)0.1773 (2)0.9070 (2)0.0537 (6)
H4A0.61530.17040.87520.064*
C50.4938 (2)0.26386 (19)1.00257 (18)0.0402 (4)
C60.3469 (3)0.2735 (2)1.04728 (19)0.0448 (5)
H6A0.32740.33161.11060.054*
C70.2297 (3)0.1976 (2)0.9987 (2)0.0476 (5)
H7A0.13220.20551.02950.057*
C80.6211 (2)0.34094 (18)1.05643 (18)0.0381 (4)
C90.7519 (2)0.46117 (19)1.17841 (18)0.0377 (4)
C100.8221 (3)0.5517 (2)1.27483 (19)0.0428 (5)
H10A0.82200.63241.23020.051*
H10B0.93660.51511.31320.051*
C110.7634 (2)0.48744 (17)1.47516 (17)0.0331 (4)
C120.8581 (2)0.36543 (18)1.47633 (19)0.0379 (4)
H12A0.90680.34021.40690.045*
C130.8792 (2)0.28157 (18)1.5822 (2)0.0427 (5)
H13A0.94270.19981.58340.051*
C140.8075 (3)0.3176 (2)1.6855 (2)0.0451 (5)
H14A0.82220.26071.75600.054*
C150.7130 (2)0.4400 (2)1.68307 (19)0.0417 (4)
H15A0.66400.46431.75260.050*
C160.6901 (2)0.52673 (17)1.57939 (18)0.0347 (4)
C170.5908 (2)0.66007 (18)1.5795 (2)0.0399 (4)
H17A0.51440.65911.63690.048*
H17B0.52530.68351.49300.048*
C180.6967 (2)0.76086 (18)1.62162 (19)0.0387 (4)
C190.6930 (3)0.9844 (2)1.6429 (3)0.0695 (8)
H19A0.61681.06471.62650.104*
H19B0.74280.97411.73360.104*
H19C0.77810.98421.59440.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0496 (4)0.0545 (4)0.0744 (4)0.0224 (3)0.0032 (3)0.0129 (3)
O10.0459 (8)0.0694 (10)0.0489 (8)0.0278 (7)0.0186 (7)0.0195 (7)
N20.0390 (9)0.0491 (9)0.0377 (8)0.0168 (7)0.0095 (7)0.0106 (7)
O40.0432 (8)0.0390 (8)0.0927 (12)0.0088 (7)0.0053 (8)0.0097 (8)
O30.0306 (8)0.0540 (9)0.0915 (12)0.0107 (6)0.0077 (7)0.0242 (8)
O20.0427 (7)0.0415 (7)0.0384 (7)0.0097 (6)0.0086 (6)0.0044 (6)
N10.0543 (11)0.0688 (12)0.0483 (10)0.0280 (9)0.0193 (8)0.0221 (9)
C10.0643 (16)0.0594 (15)0.0851 (19)0.0155 (12)0.0007 (14)0.0268 (13)
C20.0419 (11)0.0424 (11)0.0467 (11)0.0120 (8)0.0009 (8)0.0028 (8)
C30.0573 (13)0.0583 (13)0.0584 (13)0.0215 (11)0.0173 (11)0.0256 (11)
C40.0501 (12)0.0630 (14)0.0559 (13)0.0226 (11)0.0190 (10)0.0223 (11)
C50.0411 (10)0.0437 (10)0.0366 (9)0.0131 (8)0.0055 (8)0.0052 (8)
C60.0472 (11)0.0507 (11)0.0389 (10)0.0144 (9)0.0091 (9)0.0114 (8)
C70.0408 (11)0.0553 (12)0.0491 (12)0.0152 (9)0.0097 (9)0.0065 (9)
C80.0397 (10)0.0420 (10)0.0335 (9)0.0113 (8)0.0064 (8)0.0032 (7)
C90.0369 (10)0.0445 (10)0.0339 (9)0.0131 (8)0.0079 (7)0.0018 (8)
C100.0445 (11)0.0519 (11)0.0378 (10)0.0227 (9)0.0104 (8)0.0070 (8)
C110.0275 (8)0.0365 (9)0.0364 (9)0.0122 (7)0.0037 (7)0.0071 (7)
C120.0315 (9)0.0407 (10)0.0425 (10)0.0091 (7)0.0077 (7)0.0121 (8)
C130.0360 (10)0.0351 (10)0.0557 (12)0.0079 (8)0.0055 (9)0.0063 (8)
C140.0442 (11)0.0450 (11)0.0484 (11)0.0158 (9)0.0085 (9)0.0017 (9)
C150.0368 (10)0.0517 (11)0.0418 (10)0.0156 (8)0.0133 (8)0.0093 (8)
C160.0261 (8)0.0390 (10)0.0408 (10)0.0116 (7)0.0064 (7)0.0113 (8)
C170.0290 (9)0.0422 (10)0.0491 (11)0.0088 (8)0.0077 (8)0.0132 (8)
C180.0317 (10)0.0417 (10)0.0447 (10)0.0085 (8)0.0112 (8)0.0127 (8)
C190.0626 (15)0.0425 (12)0.101 (2)0.0193 (11)0.0048 (14)0.0129 (13)
Geometric parameters (Å, º) top
S—C21.757 (2)C6—C71.384 (3)
S—C11.782 (3)C6—H6A0.9300
O1—C91.334 (2)C7—H7A0.9300
O1—N11.416 (2)C9—C101.496 (3)
O2—C101.415 (2)C10—H10A0.9700
O2—C111.378 (2)C10—H10B0.9700
O3—C181.200 (2)C11—C121.388 (3)
O4—C181.339 (2)C11—C161.401 (3)
O4—C191.442 (3)C12—C131.387 (3)
N1—C81.304 (3)C12—H12A0.9300
N2—C81.380 (2)C13—C141.378 (3)
N2—C91.292 (2)C13—H13A0.9300
C1—H1B0.9600C14—C151.390 (3)
C1—H1C0.9600C14—H14A0.9300
C1—H1D0.9600C15—C161.386 (3)
C2—C71.389 (3)C15—H15A0.9300
C2—C31.395 (3)C16—C171.505 (3)
C3—C41.377 (3)C17—C181.504 (2)
C3—H3A0.9300C17—H17A0.9700
C4—C51.387 (3)C17—H17B0.9700
C4—H4A0.9300C19—H19A0.9600
C5—C61.393 (3)C19—H19B0.9600
C5—C81.468 (3)C19—H19C0.9600
C2—S—C1104.11 (12)C9—C10—H10A108.9
C9—O1—N1106.07 (14)O2—C10—H10B108.9
C11—O2—C10118.04 (15)C9—C10—H10B108.9
C18—O4—C19115.95 (17)H10A—C10—H10B107.7
C8—N1—O1103.23 (16)O2—C11—C12123.99 (17)
C9—N2—C8102.45 (16)O2—C11—C16115.13 (16)
S—C1—H1B109.5C12—C11—C16120.88 (17)
S—C1—H1C109.5C13—C12—C11119.26 (18)
H1B—C1—H1C109.5C13—C12—H12A120.4
S—C1—H1D109.5C11—C12—H12A120.4
H1B—C1—H1D109.5C14—C13—C12120.98 (18)
H1C—C1—H1D109.5C14—C13—H13A119.5
C7—C2—C3118.65 (19)C12—C13—H13A119.5
C7—C2—S117.43 (17)C13—C14—C15119.16 (19)
C3—C2—S123.89 (17)C13—C14—H14A120.4
C4—C3—C2120.6 (2)C15—C14—H14A120.4
C4—C3—H3A119.7C16—C15—C14121.49 (18)
C2—C3—H3A119.7C16—C15—H15A119.3
C3—C4—C5121.1 (2)C14—C15—H15A119.3
C3—C4—H4A119.4C15—C16—C11118.23 (17)
C5—C4—H4A119.4C15—C16—C17120.89 (17)
C4—C5—C6118.25 (19)C11—C16—C17120.87 (17)
C4—C5—C8120.43 (18)C18—C17—C16113.25 (15)
C6—C5—C8121.30 (18)C18—C17—H17A108.9
C7—C6—C5120.94 (19)C16—C17—H17A108.9
C7—C6—H6A119.5C18—C17—H17B108.9
C5—C6—H6A119.5C16—C17—H17B108.9
C6—C7—C2120.4 (2)H17A—C17—H17B107.7
C6—C7—H7A119.8O3—C18—O4122.65 (18)
C2—C7—H7A119.8O3—C18—C17126.41 (18)
N1—C8—N2114.38 (17)O4—C18—C17110.87 (16)
N1—C8—C5122.09 (18)O4—C19—H19A109.5
N2—C8—C5123.50 (17)O4—C19—H19B109.5
N2—C9—O1113.87 (17)H19A—C19—H19B109.5
N2—C9—C10130.83 (18)O4—C19—H19C109.5
O1—C9—C10115.29 (16)H19A—C19—H19C109.5
O2—C10—C9113.34 (15)H19B—C19—H19C109.5
O2—C10—H10A108.9
C1—S—C2—C36.3 (2)C3—C4—C5—C60.8 (3)
C1—S—C2—C7175.64 (19)C8—C5—C6—C7178.03 (19)
C2—S—C1—H1D59.91C6—C5—C8—N28.0 (3)
C2—S—C1—H1B179.91C4—C5—C6—C70.8 (3)
C2—S—C1—H1C60.09C4—C5—C8—N2170.72 (19)
C9—O1—N1—C80.2 (2)C6—C5—C8—N1173.9 (2)
N1—O1—C9—C10178.57 (17)C4—C5—C8—N17.4 (3)
N1—O1—C9—N20.1 (2)C5—C6—C7—C20.1 (3)
C11—O2—C10—C980.0 (2)N2—C9—C10—O28.8 (3)
C10—O2—C11—C16171.15 (17)O1—C9—C10—O2173.01 (17)
C10—O2—C11—C129.2 (3)C12—C11—C16—C17178.55 (17)
C19—O4—C18—C17179.3 (2)O2—C11—C16—C171.8 (2)
C19—O4—C18—O32.3 (3)C12—C11—C16—C150.8 (3)
O1—N1—C8—C5177.94 (17)O2—C11—C16—C15179 (3)
O1—N1—C8—N20.3 (2)C16—C11—C12—C130.3 (3)
C9—N2—C8—N10.4 (2)O2—C11—C12—C13179.30 (17)
C9—N2—C8—C5177.86 (18)C11—C12—C13—C140.1 (3)
C8—N2—C9—O10.3 (2)C12—C13—C14—C150.1 (3)
C8—N2—C9—C10178.5 (2)C13—C14—C15—C160.4 (3)
C7—C2—C3—C40.9 (3)C14—C15—C16—C110.8 (3)
S—C2—C3—C4177.11 (17)C14—C15—C16—C17178.54 (19)
S—C2—C7—C6177.18 (17)C15—C16—C17—C1897.3 (2)
C3—C2—C7—C61.0 (3)C11—C16—C17—C1882.0 (2)
C2—C3—C4—C50.00C16—C17—C18—O4172.09 (17)
C3—C4—C5—C8177.98 (19)C16—C17—C18—O311.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O3i0.932.433.257 (3)148
C10—H10A···Cg2ii0.972.773.58142
C10—H10B···Cg3i0.972.653.43138
C17—H17B···Cg3iii0.972.853.42118
Symmetry codes: (i) x+2, y1, z+3; (ii) x+1, y1, z+2; (iii) x+1, y1, z+3.
 

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