


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811025785/jh2306sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536811025785/jh2306Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811025785/jh2306Isup3.cml |
CCDC reference: 841152
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.110
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers . 3
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 -- C8 .. 5.9 su PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 18
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ?
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 1 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The title compound was prepared according to a previously reported procedure (Al-abbasi et al., 2010) using 3-methoxybenzoyl chloride and diphenylamine as the appropriate starting materials. A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from ethanol solution at room temperature (yield 75%).
Hydrogen atom of the amide group was determined from the difference Fourier map and N—H was initially fixed at 0.86(0.01) Å and allowed to be refined on the parent N atom with Uiso(H) = 1.2Ueq(N). All other H atoms were positioned geometrically with C—H bond lengths in the range 0.93 - 0.97 Å and refined in the riding model approximation with Uiso(H)=1.2Ueq(C,N), except for methyl group where Uiso(H)= 1.5Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
C21H18N2O2S | Z = 2 |
Mr = 362.43 | F(000) = 380 |
Triclinic, P1 | Dx = 1.308 Mg m−3 |
Hall symbol: -P 1 | Melting point = 412.15–410.15 K |
a = 6.056 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.895 (7) Å | Cell parameters from 3612 reflections |
c = 13.344 (7) Å | θ = 6.4–55.2° |
α = 112.796 (9)° | µ = 0.19 mm−1 |
β = 100.336 (10)° | T = 298 K |
γ = 97.951 (10)° | Plate, yellow |
V = 920.0 (8) Å3 | 0.52 × 0.23 × 0.03 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3612 independent reflections |
Radiation source: fine-focus sealed tube | 2663 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scan | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→7 |
Tmin = 0.906, Tmax = 0.994 | k = −15→15 |
10189 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1546P] where P = (Fo2 + 2Fc2)/3 |
3612 reflections | (Δ/σ)max < 0.001 |
240 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C21H18N2O2S | γ = 97.951 (10)° |
Mr = 362.43 | V = 920.0 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.056 (3) Å | Mo Kα radiation |
b = 12.895 (7) Å | µ = 0.19 mm−1 |
c = 13.344 (7) Å | T = 298 K |
α = 112.796 (9)° | 0.52 × 0.23 × 0.03 mm |
β = 100.336 (10)° |
Bruker SMART APEX CCD area-detector diffractometer | 3612 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2663 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.994 | Rint = 0.029 |
10189 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.17 e Å−3 |
3612 reflections | Δρmin = −0.27 e Å−3 |
240 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 | ||
S1 | 0.28578 (10) | 0.32442 (4) | 0.43411 (4) | 0.05684 (19) | |
O1 | 0.0958 (3) | 0.92764 (11) | 0.40494 (14) | 0.0667 (4) | |
O2 | −0.0666 (2) | 0.49768 (10) | 0.27758 (12) | 0.0554 (4) | |
N1 | 0.2897 (3) | 0.47668 (11) | 0.34630 (12) | 0.0403 (4) | |
N2 | 0.0990 (2) | 0.28974 (11) | 0.22465 (10) | 0.0372 (3) | |
C6 | 0.4600 (3) | 0.67429 (15) | 0.30353 (15) | 0.0458 (4) | |
H6 | 0.5408 | 0.6164 | 0.2821 | 0.055* | |
C5 | 0.5442 (3) | 0.78217 (16) | 0.30918 (17) | 0.0504 (5) | |
H5 | 0.6817 | 0.7962 | 0.2898 | 0.060* | |
C4 | 0.4287 (3) | 0.86899 (15) | 0.34293 (15) | 0.0458 (4) | |
H4 | 0.4889 | 0.9413 | 0.3471 | 0.055* | |
C3 | 0.2235 (3) | 0.84874 (14) | 0.37065 (15) | 0.0438 (4) | |
C2 | 0.1354 (3) | 0.74050 (14) | 0.36416 (14) | 0.0430 (4) | |
H2 | −0.0031 | 0.7264 | 0.3827 | 0.052* | |
C1 | 0.2519 (3) | 0.65424 (13) | 0.33049 (13) | 0.0380 (4) | |
C21 | 0.1482 (4) | 1.03154 (16) | 0.39139 (19) | 0.0595 (5) | |
H21A | 0.2992 | 1.0754 | 0.4378 | 0.089* | |
H21B | 0.0366 | 1.0762 | 0.4132 | 0.089* | |
H21C | 0.1443 | 1.0132 | 0.3141 | 0.089* | |
C7 | 0.1389 (3) | 0.53717 (14) | 0.31542 (14) | 0.0405 (4) | |
C8 | 0.2192 (3) | 0.36345 (13) | 0.33048 (13) | 0.0376 (4) | |
C9 | 0.1204 (3) | 0.31150 (13) | 0.12858 (13) | 0.0369 (4) | |
C14 | −0.0742 (3) | 0.29310 (16) | 0.04667 (14) | 0.0476 (4) | |
H14 | −0.2192 | 0.2659 | 0.0529 | 0.057* | |
C13 | −0.0526 (4) | 0.31537 (19) | −0.04475 (16) | 0.0610 (6) | |
H13 | −0.1836 | 0.3029 | −0.1002 | 0.073* | |
C12 | 0.1610 (4) | 0.35575 (19) | −0.05447 (17) | 0.0618 (6) | |
H12 | 0.1745 | 0.3719 | −0.1155 | 0.074* | |
C11 | 0.3535 (4) | 0.37199 (18) | 0.02626 (18) | 0.0579 (5) | |
H11 | 0.4983 | 0.3987 | 0.0195 | 0.070* | |
C10 | 0.3355 (3) | 0.34923 (15) | 0.11738 (15) | 0.0464 (4) | |
H10 | 0.4675 | 0.3592 | 0.1712 | 0.056* | |
C15 | −0.0664 (3) | 0.18826 (13) | 0.20578 (13) | 0.0388 (4) | |
C16 | −0.2480 (3) | 0.20071 (17) | 0.25501 (16) | 0.0523 (5) | |
H16 | −0.2582 | 0.2736 | 0.3035 | 0.063* | |
C17 | −0.4148 (4) | 0.1046 (2) | 0.2320 (2) | 0.0697 (6) | |
H17 | −0.5374 | 0.1125 | 0.2654 | 0.084* | |
C18 | −0.4001 (4) | −0.0022 (2) | 0.16034 (19) | 0.0757 (8) | |
H18 | −0.5141 | −0.0668 | 0.1442 | 0.091* | |
C19 | −0.2184 (4) | −0.01469 (17) | 0.11210 (17) | 0.0691 (7) | |
H19 | −0.2089 | −0.0879 | 0.0640 | 0.083* | |
C20 | −0.0481 (4) | 0.08113 (14) | 0.13453 (14) | 0.0505 (5) | |
H20 | 0.0756 | 0.0729 | 0.1020 | 0.061* | |
H1A | 0.416 (3) | 0.5170 (16) | 0.3974 (17) | 0.049 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0816 (4) | 0.0375 (2) | 0.0398 (3) | −0.0063 (2) | −0.0094 (2) | 0.02171 (19) |
O1 | 0.0816 (11) | 0.0378 (7) | 0.1021 (12) | 0.0228 (7) | 0.0492 (9) | 0.0372 (7) |
O2 | 0.0428 (8) | 0.0374 (7) | 0.0779 (9) | 0.0029 (6) | 0.0069 (7) | 0.0217 (6) |
N1 | 0.0461 (9) | 0.0274 (7) | 0.0387 (7) | −0.0018 (6) | −0.0051 (7) | 0.0153 (6) |
N2 | 0.0446 (8) | 0.0302 (7) | 0.0328 (7) | 0.0003 (6) | 0.0040 (6) | 0.0142 (5) |
C6 | 0.0488 (11) | 0.0418 (9) | 0.0496 (10) | 0.0113 (8) | 0.0086 (8) | 0.0238 (8) |
C5 | 0.0430 (10) | 0.0521 (11) | 0.0630 (12) | 0.0058 (9) | 0.0131 (9) | 0.0333 (9) |
C4 | 0.0488 (11) | 0.0375 (9) | 0.0517 (10) | 0.0015 (8) | 0.0055 (8) | 0.0253 (8) |
C3 | 0.0518 (11) | 0.0335 (9) | 0.0469 (9) | 0.0085 (8) | 0.0110 (8) | 0.0188 (7) |
C2 | 0.0461 (10) | 0.0367 (9) | 0.0495 (10) | 0.0072 (8) | 0.0132 (8) | 0.0218 (8) |
C1 | 0.0430 (10) | 0.0328 (8) | 0.0361 (8) | 0.0026 (7) | 0.0026 (7) | 0.0176 (7) |
C21 | 0.0784 (15) | 0.0376 (10) | 0.0712 (13) | 0.0151 (10) | 0.0196 (11) | 0.0313 (10) |
C7 | 0.0489 (11) | 0.0310 (8) | 0.0379 (8) | 0.0046 (7) | 0.0078 (7) | 0.0137 (7) |
C8 | 0.0401 (9) | 0.0309 (8) | 0.0372 (8) | 0.0020 (7) | 0.0029 (7) | 0.0147 (7) |
C9 | 0.0448 (10) | 0.0315 (8) | 0.0334 (8) | 0.0053 (7) | 0.0072 (7) | 0.0152 (6) |
C14 | 0.0459 (11) | 0.0524 (10) | 0.0402 (9) | 0.0039 (8) | 0.0045 (8) | 0.0205 (8) |
C13 | 0.0669 (14) | 0.0732 (13) | 0.0408 (10) | 0.0146 (11) | 0.0008 (9) | 0.0283 (10) |
C12 | 0.0808 (16) | 0.0711 (14) | 0.0466 (11) | 0.0179 (12) | 0.0230 (11) | 0.0353 (10) |
C11 | 0.0609 (13) | 0.0614 (12) | 0.0640 (12) | 0.0120 (10) | 0.0276 (10) | 0.0350 (10) |
C10 | 0.0463 (11) | 0.0460 (10) | 0.0472 (10) | 0.0078 (8) | 0.0090 (8) | 0.0223 (8) |
C15 | 0.0432 (10) | 0.0341 (8) | 0.0340 (8) | −0.0015 (7) | 0.0017 (7) | 0.0162 (7) |
C16 | 0.0512 (12) | 0.0517 (11) | 0.0542 (11) | 0.0064 (9) | 0.0130 (9) | 0.0247 (9) |
C17 | 0.0547 (13) | 0.0831 (16) | 0.0705 (14) | −0.0078 (12) | 0.0141 (11) | 0.0403 (13) |
C18 | 0.0862 (17) | 0.0643 (14) | 0.0560 (12) | −0.0330 (12) | 0.0002 (12) | 0.0286 (11) |
C19 | 0.1047 (19) | 0.0375 (10) | 0.0451 (11) | −0.0142 (11) | 0.0102 (12) | 0.0110 (8) |
C20 | 0.0684 (13) | 0.0364 (9) | 0.0386 (9) | 0.0007 (9) | 0.0121 (9) | 0.0118 (7) |
S1—C8 | 1.6503 (17) | C21—H21C | 0.9600 |
O1—C3 | 1.351 (2) | C9—C14 | 1.378 (2) |
O1—C21 | 1.421 (2) | C9—C10 | 1.381 (3) |
O2—C7 | 1.210 (2) | C14—C13 | 1.381 (3) |
N1—C8 | 1.384 (2) | C14—H14 | 0.9300 |
N1—C7 | 1.387 (2) | C13—C12 | 1.373 (3) |
N1—H1A | 0.87 (2) | C13—H13 | 0.9300 |
N2—C8 | 1.352 (2) | C12—C11 | 1.368 (3) |
N2—C9 | 1.438 (2) | C12—H12 | 0.9300 |
N2—C15 | 1.439 (2) | C11—C10 | 1.375 (3) |
C6—C5 | 1.382 (2) | C11—H11 | 0.9300 |
C6—C1 | 1.389 (3) | C10—H10 | 0.9300 |
C6—H6 | 0.9300 | C15—C20 | 1.374 (3) |
C5—C4 | 1.373 (3) | C15—C16 | 1.376 (3) |
C5—H5 | 0.9300 | C16—C17 | 1.377 (3) |
C4—C3 | 1.378 (3) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—C18 | 1.365 (4) |
C3—C2 | 1.387 (2) | C17—H17 | 0.9300 |
C2—C1 | 1.371 (3) | C18—C19 | 1.369 (4) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C1—C7 | 1.489 (2) | C19—C20 | 1.389 (3) |
C21—H21A | 0.9600 | C19—H19 | 0.9300 |
C21—H21B | 0.9600 | C20—H20 | 0.9300 |
C3—O1—C21 | 118.49 (16) | C14—C9—C10 | 119.92 (16) |
C8—N1—C7 | 122.68 (15) | C14—C9—N2 | 119.86 (15) |
C8—N1—H1A | 116.5 (13) | C10—C9—N2 | 120.21 (15) |
C7—N1—H1A | 117.1 (13) | C9—C14—C13 | 119.56 (18) |
C8—N2—C9 | 122.38 (13) | C9—C14—H14 | 120.2 |
C8—N2—C15 | 119.92 (13) | C13—C14—H14 | 120.2 |
C9—N2—C15 | 117.62 (12) | C12—C13—C14 | 120.52 (19) |
C5—C6—C1 | 118.54 (17) | C12—C13—H13 | 119.7 |
C5—C6—H6 | 120.7 | C14—C13—H13 | 119.7 |
C1—C6—H6 | 120.7 | C11—C12—C13 | 119.54 (18) |
C4—C5—C6 | 121.22 (18) | C11—C12—H12 | 120.2 |
C4—C5—H5 | 119.4 | C13—C12—H12 | 120.2 |
C6—C5—H5 | 119.4 | C12—C11—C10 | 120.76 (19) |
C5—C4—C3 | 119.88 (16) | C12—C11—H11 | 119.6 |
C5—C4—H4 | 120.1 | C10—C11—H11 | 119.6 |
C3—C4—H4 | 120.1 | C11—C10—C9 | 119.66 (18) |
O1—C3—C4 | 124.89 (15) | C11—C10—H10 | 120.2 |
O1—C3—C2 | 115.53 (16) | C9—C10—H10 | 120.2 |
C4—C3—C2 | 119.57 (17) | C20—C15—C16 | 120.88 (16) |
C1—C2—C3 | 120.20 (17) | C20—C15—N2 | 119.82 (16) |
C1—C2—H2 | 119.9 | C16—C15—N2 | 119.20 (16) |
C3—C2—H2 | 119.9 | C15—C16—C17 | 119.6 (2) |
C2—C1—C6 | 120.58 (15) | C15—C16—H16 | 120.2 |
C2—C1—C7 | 117.72 (16) | C17—C16—H16 | 120.2 |
C6—C1—C7 | 121.53 (16) | C18—C17—C16 | 120.1 (2) |
O1—C21—H21A | 109.5 | C18—C17—H17 | 120.0 |
O1—C21—H21B | 109.5 | C16—C17—H17 | 120.0 |
H21A—C21—H21B | 109.5 | C17—C18—C19 | 120.30 (19) |
O1—C21—H21C | 109.5 | C17—C18—H18 | 119.9 |
H21A—C21—H21C | 109.5 | C19—C18—H18 | 119.9 |
H21B—C21—H21C | 109.5 | C18—C19—C20 | 120.5 (2) |
O2—C7—N1 | 123.01 (15) | C18—C19—H19 | 119.8 |
O2—C7—C1 | 122.65 (16) | C20—C19—H19 | 119.8 |
N1—C7—C1 | 114.33 (15) | C15—C20—C19 | 118.6 (2) |
N2—C8—N1 | 114.68 (14) | C15—C20—H20 | 120.7 |
N2—C8—S1 | 124.04 (12) | C19—C20—H20 | 120.7 |
N1—C8—S1 | 121.26 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1i | 0.87 (2) | 2.54 (2) | 3.380 (2) | 163.6 (17) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H18N2O2S |
Mr | 362.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 6.056 (3), 12.895 (7), 13.344 (7) |
α, β, γ (°) | 112.796 (9), 100.336 (10), 97.951 (10) |
V (Å3) | 920.0 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.52 × 0.23 × 0.03 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.906, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10189, 3612, 2663 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.110, 1.04 |
No. of reflections | 3612 |
No. of parameters | 240 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.27 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1i | 0.87 (2) | 2.54 (2) | 3.380 (2) | 163.6 (17) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Benzoylthiourea compounds act as a chelating ligands by deprotonation of the amide group and coordinate via a thiolate form through the S and O atoms to form neutral complexes with cobalt (Weiqun et al., 2005) and platinum (Circu et al., 2009).
The title compound, I, is a thiourea derivative analogous to our previously reported compounds (Md Nasir et al., 2011; Al-abbasi & Kassim, 2011). The thiono and the carbonyl groups are trans positioned with respect to N1—C8 bond with C7N1C8S1 torsion angle of -129.10 (16)°. The methoxy group is coplanar with the parent benzene ring with the largest deviation from the mean planes of (O1/C1/C2/C3/C4/C5/C6/C7) of -0.051 (2)° for C7 and the dihedral angle between the same plane and the thioamide mean planes (S1/N1/N2/C8) is 87.45 (8)°.
In the crystal structure, Intermolecular N1—H1A···S1 hydrogen bond link the molecules into a centrosymmetric dimers forming channel parallel to the a-axis.