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The title compound, C
19H
18N
2O
4S, 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
CCDC reference: 255936
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C19H18N2O4S | Z = 2 |
Mr = 370.41 | F(000) = 388 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
a = 8.3580 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.522 (2) Å | Cell parameters from 25 reflections |
c = 10.581 (2) Å | θ = 10–13° |
α = 90.13 (3)° | µ = 0.21 mm−1 |
β = 102.08 (3)° | T = 293 K |
γ = 99.73 (3)° | Block, colourless |
V = 896.1 (3) Å3 | 0.4 × 0.3 × 0.3 mm |
Data collection top
Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.0° |
Graphite monochromator | h = 0→10 |
ω/2θ scans | k = −12→12 |
3752 measured reflections | l = −13→12 |
3499 independent reflections | 3 standard reflections every 200 reflections |
2763 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.32 e Å−3 |
236 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S | 0.10592 (7) | −0.01231 (6) | 0.85337 (7) | 0.0594 (2) | |
O1 | 0.84214 (18) | −0.42310 (16) | 1.09084 (14) | 0.0513 (4) | |
N2 | 0.6154 (2) | −0.41523 (16) | 1.16328 (15) | 0.0406 (4) | |
O4 | 0.60500 (19) | −0.87935 (14) | 1.60436 (19) | 0.0610 (5) | |
O3 | 0.84235 (17) | −0.74158 (15) | 1.66992 (18) | 0.0590 (5) | |
O2 | 0.73315 (17) | −0.57758 (13) | 1.37455 (13) | 0.0406 (3) | |
N1 | 0.7524 (2) | −0.3417 (2) | 1.00828 (18) | 0.0538 (5) | |
C1 | 0.1752 (3) | 0.0760 (3) | 0.7257 (3) | 0.0715 (8) | |
H1B | 0.0988 | 0.1325 | 0.6921 | 0.107* | |
H1C | 0.1807 | 0.0171 | 0.6580 | 0.107* | |
H1D | 0.2834 | 0.1261 | 0.7582 | 0.107* | |
C2 | 0.2567 (3) | −0.1099 (2) | 0.9043 (2) | 0.0444 (5) | |
C3 | 0.4027 (3) | −0.1014 (2) | 0.8583 (2) | 0.0559 (6) | |
H3A | 0.4219 | −0.0440 | 0.7942 | 0.067* | |
C4 | 0.5187 (3) | −0.1773 (2) | 0.9070 (2) | 0.0537 (6) | |
H4A | 0.6153 | −0.1704 | 0.8752 | 0.064* | |
C5 | 0.4938 (2) | −0.26386 (19) | 1.00257 (18) | 0.0402 (4) | |
C6 | 0.3469 (3) | −0.2735 (2) | 1.04728 (19) | 0.0448 (5) | |
H6A | 0.3274 | −0.3316 | 1.1106 | 0.054* | |
C7 | 0.2297 (3) | −0.1976 (2) | 0.9987 (2) | 0.0476 (5) | |
H7A | 0.1322 | −0.2055 | 1.0295 | 0.057* | |
C8 | 0.6211 (2) | −0.34094 (18) | 1.05643 (18) | 0.0381 (4) | |
C9 | 0.7519 (2) | −0.46117 (19) | 1.17841 (18) | 0.0377 (4) | |
C10 | 0.8221 (3) | −0.5517 (2) | 1.27483 (19) | 0.0428 (5) | |
H10A | 0.8220 | −0.6324 | 1.2302 | 0.051* | |
H10B | 0.9366 | −0.5151 | 1.3132 | 0.051* | |
C11 | 0.7634 (2) | −0.48744 (17) | 1.47516 (17) | 0.0331 (4) | |
C12 | 0.8581 (2) | −0.36543 (18) | 1.47633 (19) | 0.0379 (4) | |
H12A | 0.9068 | −0.3402 | 1.4069 | 0.045* | |
C13 | 0.8792 (2) | −0.28157 (18) | 1.5822 (2) | 0.0427 (5) | |
H13A | 0.9427 | −0.1998 | 1.5834 | 0.051* | |
C14 | 0.8075 (3) | −0.3176 (2) | 1.6855 (2) | 0.0451 (5) | |
H14A | 0.8222 | −0.2607 | 1.7560 | 0.054* | |
C15 | 0.7130 (2) | −0.4400 (2) | 1.68307 (19) | 0.0417 (4) | |
H15A | 0.6640 | −0.4643 | 1.7526 | 0.050* | |
C16 | 0.6901 (2) | −0.52673 (17) | 1.57939 (18) | 0.0347 (4) | |
C17 | 0.5908 (2) | −0.66007 (18) | 1.5795 (2) | 0.0399 (4) | |
H17A | 0.5144 | −0.6591 | 1.6369 | 0.048* | |
H17B | 0.5253 | −0.6835 | 1.4930 | 0.048* | |
C18 | 0.6967 (2) | −0.76086 (18) | 1.62162 (19) | 0.0387 (4) | |
C19 | 0.6930 (3) | −0.9844 (2) | 1.6429 (3) | 0.0695 (8) | |
H19A | 0.6168 | −1.0647 | 1.6265 | 0.104* | |
H19B | 0.7428 | −0.9741 | 1.7336 | 0.104* | |
H19C | 0.7781 | −0.9842 | 1.5944 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0496 (4) | 0.0545 (4) | 0.0744 (4) | 0.0224 (3) | 0.0032 (3) | 0.0129 (3) |
O1 | 0.0459 (8) | 0.0694 (10) | 0.0489 (8) | 0.0278 (7) | 0.0186 (7) | 0.0195 (7) |
N2 | 0.0390 (9) | 0.0491 (9) | 0.0377 (8) | 0.0168 (7) | 0.0095 (7) | 0.0106 (7) |
O4 | 0.0432 (8) | 0.0390 (8) | 0.0927 (12) | 0.0088 (7) | −0.0053 (8) | 0.0097 (8) |
O3 | 0.0306 (8) | 0.0540 (9) | 0.0915 (12) | 0.0107 (6) | 0.0077 (7) | 0.0242 (8) |
O2 | 0.0427 (7) | 0.0415 (7) | 0.0384 (7) | 0.0097 (6) | 0.0086 (6) | 0.0044 (6) |
N1 | 0.0543 (11) | 0.0688 (12) | 0.0483 (10) | 0.0280 (9) | 0.0193 (8) | 0.0221 (9) |
C1 | 0.0643 (16) | 0.0594 (15) | 0.0851 (19) | 0.0155 (12) | −0.0007 (14) | 0.0268 (13) |
C2 | 0.0419 (11) | 0.0424 (11) | 0.0467 (11) | 0.0120 (8) | 0.0009 (8) | 0.0028 (8) |
C3 | 0.0573 (13) | 0.0583 (13) | 0.0584 (13) | 0.0215 (11) | 0.0173 (11) | 0.0256 (11) |
C4 | 0.0501 (12) | 0.0630 (14) | 0.0559 (13) | 0.0226 (11) | 0.0190 (10) | 0.0223 (11) |
C5 | 0.0411 (10) | 0.0437 (10) | 0.0366 (9) | 0.0131 (8) | 0.0055 (8) | 0.0052 (8) |
C6 | 0.0472 (11) | 0.0507 (11) | 0.0389 (10) | 0.0144 (9) | 0.0091 (9) | 0.0114 (8) |
C7 | 0.0408 (11) | 0.0553 (12) | 0.0491 (12) | 0.0152 (9) | 0.0097 (9) | 0.0065 (9) |
C8 | 0.0397 (10) | 0.0420 (10) | 0.0335 (9) | 0.0113 (8) | 0.0064 (8) | 0.0032 (7) |
C9 | 0.0369 (10) | 0.0445 (10) | 0.0339 (9) | 0.0131 (8) | 0.0079 (7) | 0.0018 (8) |
C10 | 0.0445 (11) | 0.0519 (11) | 0.0378 (10) | 0.0227 (9) | 0.0104 (8) | 0.0070 (8) |
C11 | 0.0275 (8) | 0.0365 (9) | 0.0364 (9) | 0.0122 (7) | 0.0037 (7) | 0.0071 (7) |
C12 | 0.0315 (9) | 0.0407 (10) | 0.0425 (10) | 0.0091 (7) | 0.0077 (7) | 0.0121 (8) |
C13 | 0.0360 (10) | 0.0351 (10) | 0.0557 (12) | 0.0079 (8) | 0.0055 (9) | 0.0063 (8) |
C14 | 0.0442 (11) | 0.0450 (11) | 0.0484 (11) | 0.0158 (9) | 0.0085 (9) | −0.0017 (9) |
C15 | 0.0368 (10) | 0.0517 (11) | 0.0418 (10) | 0.0156 (8) | 0.0133 (8) | 0.0093 (8) |
C16 | 0.0261 (8) | 0.0390 (10) | 0.0408 (10) | 0.0116 (7) | 0.0064 (7) | 0.0113 (8) |
C17 | 0.0290 (9) | 0.0422 (10) | 0.0491 (11) | 0.0088 (8) | 0.0077 (8) | 0.0132 (8) |
C18 | 0.0317 (10) | 0.0417 (10) | 0.0447 (10) | 0.0085 (8) | 0.0112 (8) | 0.0127 (8) |
C19 | 0.0626 (15) | 0.0425 (12) | 0.101 (2) | 0.0193 (11) | 0.0048 (14) | 0.0129 (13) |
Geometric parameters (Å, º) top
S—C2 | 1.757 (2) | C6—C7 | 1.384 (3) |
S—C1 | 1.782 (3) | C6—H6A | 0.9300 |
O1—C9 | 1.334 (2) | C7—H7A | 0.9300 |
O1—N1 | 1.416 (2) | C9—C10 | 1.496 (3) |
O2—C10 | 1.415 (2) | C10—H10A | 0.9700 |
O2—C11 | 1.378 (2) | C10—H10B | 0.9700 |
O3—C18 | 1.200 (2) | C11—C12 | 1.388 (3) |
O4—C18 | 1.339 (2) | C11—C16 | 1.401 (3) |
O4—C19 | 1.442 (3) | C12—C13 | 1.387 (3) |
N1—C8 | 1.304 (3) | C12—H12A | 0.9300 |
N2—C8 | 1.380 (2) | C13—C14 | 1.378 (3) |
N2—C9 | 1.292 (2) | C13—H13A | 0.9300 |
C1—H1B | 0.9600 | C14—C15 | 1.390 (3) |
C1—H1C | 0.9600 | C14—H14A | 0.9300 |
C1—H1D | 0.9600 | C15—C16 | 1.386 (3) |
C2—C7 | 1.389 (3) | C15—H15A | 0.9300 |
C2—C3 | 1.395 (3) | C16—C17 | 1.505 (3) |
C3—C4 | 1.377 (3) | C17—C18 | 1.504 (2) |
C3—H3A | 0.9300 | C17—H17A | 0.9700 |
C4—C5 | 1.387 (3) | C17—H17B | 0.9700 |
C4—H4A | 0.9300 | C19—H19A | 0.9600 |
C5—C6 | 1.393 (3) | C19—H19B | 0.9600 |
C5—C8 | 1.468 (3) | C19—H19C | 0.9600 |
| | | |
C2—S—C1 | 104.11 (12) | C9—C10—H10A | 108.9 |
C9—O1—N1 | 106.07 (14) | O2—C10—H10B | 108.9 |
C11—O2—C10 | 118.04 (15) | C9—C10—H10B | 108.9 |
C18—O4—C19 | 115.95 (17) | H10A—C10—H10B | 107.7 |
C8—N1—O1 | 103.23 (16) | O2—C11—C12 | 123.99 (17) |
C9—N2—C8 | 102.45 (16) | O2—C11—C16 | 115.13 (16) |
S—C1—H1B | 109.5 | C12—C11—C16 | 120.88 (17) |
S—C1—H1C | 109.5 | C13—C12—C11 | 119.26 (18) |
H1B—C1—H1C | 109.5 | C13—C12—H12A | 120.4 |
S—C1—H1D | 109.5 | C11—C12—H12A | 120.4 |
H1B—C1—H1D | 109.5 | C14—C13—C12 | 120.98 (18) |
H1C—C1—H1D | 109.5 | C14—C13—H13A | 119.5 |
C7—C2—C3 | 118.65 (19) | C12—C13—H13A | 119.5 |
C7—C2—S | 117.43 (17) | C13—C14—C15 | 119.16 (19) |
C3—C2—S | 123.89 (17) | C13—C14—H14A | 120.4 |
C4—C3—C2 | 120.6 (2) | C15—C14—H14A | 120.4 |
C4—C3—H3A | 119.7 | C16—C15—C14 | 121.49 (18) |
C2—C3—H3A | 119.7 | C16—C15—H15A | 119.3 |
C3—C4—C5 | 121.1 (2) | C14—C15—H15A | 119.3 |
C3—C4—H4A | 119.4 | C15—C16—C11 | 118.23 (17) |
C5—C4—H4A | 119.4 | C15—C16—C17 | 120.89 (17) |
C4—C5—C6 | 118.25 (19) | C11—C16—C17 | 120.87 (17) |
C4—C5—C8 | 120.43 (18) | C18—C17—C16 | 113.25 (15) |
C6—C5—C8 | 121.30 (18) | C18—C17—H17A | 108.9 |
C7—C6—C5 | 120.94 (19) | C16—C17—H17A | 108.9 |
C7—C6—H6A | 119.5 | C18—C17—H17B | 108.9 |
C5—C6—H6A | 119.5 | C16—C17—H17B | 108.9 |
C6—C7—C2 | 120.4 (2) | H17A—C17—H17B | 107.7 |
C6—C7—H7A | 119.8 | O3—C18—O4 | 122.65 (18) |
C2—C7—H7A | 119.8 | O3—C18—C17 | 126.41 (18) |
N1—C8—N2 | 114.38 (17) | O4—C18—C17 | 110.87 (16) |
N1—C8—C5 | 122.09 (18) | O4—C19—H19A | 109.5 |
N2—C8—C5 | 123.50 (17) | O4—C19—H19B | 109.5 |
N2—C9—O1 | 113.87 (17) | H19A—C19—H19B | 109.5 |
N2—C9—C10 | 130.83 (18) | O4—C19—H19C | 109.5 |
O1—C9—C10 | 115.29 (16) | H19A—C19—H19C | 109.5 |
O2—C10—C9 | 113.34 (15) | H19B—C19—H19C | 109.5 |
O2—C10—H10A | 108.9 | | |
| | | |
C1—S—C2—C3 | 6.3 (2) | C3—C4—C5—C6 | 0.8 (3) |
C1—S—C2—C7 | −175.64 (19) | C8—C5—C6—C7 | 178.03 (19) |
C2—S—C1—H1D | −59.91 | C6—C5—C8—N2 | −8.0 (3) |
C2—S—C1—H1B | −179.91 | C4—C5—C6—C7 | −0.8 (3) |
C2—S—C1—H1C | 60.09 | C4—C5—C8—N2 | 170.72 (19) |
C9—O1—N1—C8 | 0.2 (2) | C6—C5—C8—N1 | 173.9 (2) |
N1—O1—C9—C10 | 178.57 (17) | C4—C5—C8—N1 | −7.4 (3) |
N1—O1—C9—N2 | 0.1 (2) | C5—C6—C7—C2 | −0.1 (3) |
C11—O2—C10—C9 | −80.0 (2) | N2—C9—C10—O2 | −8.8 (3) |
C10—O2—C11—C16 | −171.15 (17) | O1—C9—C10—O2 | 173.01 (17) |
C10—O2—C11—C12 | 9.2 (3) | C12—C11—C16—C17 | −178.55 (17) |
C19—O4—C18—C17 | −179.3 (2) | O2—C11—C16—C17 | 1.8 (2) |
C19—O4—C18—O3 | −2.3 (3) | C12—C11—C16—C15 | 0.8 (3) |
O1—N1—C8—C5 | 177.94 (17) | O2—C11—C16—C15 | −179 (3) |
O1—N1—C8—N2 | −0.3 (2) | C16—C11—C12—C13 | −0.3 (3) |
C9—N2—C8—N1 | 0.4 (2) | O2—C11—C12—C13 | 179.30 (17) |
C9—N2—C8—C5 | −177.86 (18) | C11—C12—C13—C14 | −0.1 (3) |
C8—N2—C9—O1 | −0.3 (2) | C12—C13—C14—C15 | 0.1 (3) |
C8—N2—C9—C10 | −178.5 (2) | C13—C14—C15—C16 | 0.4 (3) |
C7—C2—C3—C4 | −0.9 (3) | C14—C15—C16—C11 | −0.8 (3) |
S—C2—C3—C4 | 177.11 (17) | C14—C15—C16—C17 | 178.54 (19) |
S—C2—C7—C6 | −177.18 (17) | C15—C16—C17—C18 | −97.3 (2) |
C3—C2—C7—C6 | 1.0 (3) | C11—C16—C17—C18 | 82.0 (2) |
C2—C3—C4—C5 | 0.00 | C16—C17—C18—O4 | −172.09 (17) |
C3—C4—C5—C8 | −177.98 (19) | C16—C17—C18—O3 | 11.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O3i | 0.93 | 2.43 | 3.257 (3) | 148 |
C10—H10A···Cg2ii | 0.97 | 2.77 | 3.58 | 142 |
C10—H10B···Cg3i | 0.97 | 2.65 | 3.43 | 138 |
C17—H17B···Cg3iii | 0.97 | 2.85 | 3.42 | 118 |
Symmetry codes: (i) −x+2, −y−1, −z+3; (ii) −x+1, −y−1, −z+2; (iii) −x+1, −y−1, −z+3. |
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