Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029478/at6031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029478/at6031Isup2.hkl |
CCDC reference: 287437
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.114
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion
To a stirred acetone solution (75 ml) of anisoyl chloride (2.5 g, 20 mmol) and ammonium thiocyanate (2.1 ml, 20 mmol), p-toulidine (2.8 ml, 20 mmol) was added dropwise. The solution mixture was refluxed for 3 h. The resulting solution was poured into a beaker containing ice cubes. The white precipitate was filtered off and washed with distilled water and cold ethanol, and then dried in a vacuum. Good quality single crystals were obtained by recrystallization from dimethyl sulfoxide.
After their location in a difference map, all H atoms were fixed geometrically at ideal positions and allowed to ride on their parent C or N atoms, with C—H = 0.93–0.96 Å and N—H = 0.86 Å, and Uiso(H) = 1.2Ueq(C,N) for CH2 and NH, and 1.5Ueq(C) for CH3.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C16H16N2O2S | Z = 2 |
Mr = 300.37 | F(000) = 316 |
Triclinic, P1 | Dx = 1.306 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.3676 (9) Å | Cell parameters from 951 reflections |
b = 11.4763 (19) Å | θ = 1.6–25.5° |
c = 12.447 (2) Å | µ = 0.22 mm−1 |
α = 92.505 (3)° | T = 293 K |
β = 91.692 (3)° | Block, colourless |
γ = 94.138 (3)° | 0.45 × 0.39 × 0.30 mm |
V = 763.6 (2) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 2827 independent reflections |
Radiation source: fine-focus sealed tube | 2492 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.5°, θmin = 1.6° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.90, Tmax = 0.93 | l = −15→15 |
7554 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.149P] where P = (Fo2 + 2Fc2)/3 |
2827 reflections | (Δ/σ)max < 0.001 |
192 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C16H16N2O2S | γ = 94.138 (3)° |
Mr = 300.37 | V = 763.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.3676 (9) Å | Mo Kα radiation |
b = 11.4763 (19) Å | µ = 0.22 mm−1 |
c = 12.447 (2) Å | T = 293 K |
α = 92.505 (3)° | 0.45 × 0.39 × 0.30 mm |
β = 91.692 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 2827 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2492 reflections with I > 2σ(I) |
Tmin = 0.90, Tmax = 0.93 | Rint = 0.016 |
7554 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.21 e Å−3 |
2827 reflections | Δρmin = −0.16 e Å−3 |
192 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.34628 (10) | 0.62356 (4) | 0.90403 (4) | 0.05940 (19) | |
O1 | 0.4928 (3) | 0.33017 (13) | 0.66361 (10) | 0.0736 (4) | |
O2 | 1.2697 (3) | 0.04294 (12) | 0.91575 (13) | 0.0755 (4) | |
N1 | 0.5264 (3) | 0.43374 (11) | 0.82421 (11) | 0.0459 (3) | |
H1A | 0.5934 | 0.4343 | 0.8879 | 0.055* | |
N2 | 0.2645 (3) | 0.52187 (12) | 0.70791 (11) | 0.0501 (4) | |
H2A | 0.2857 | 0.4620 | 0.6661 | 0.060* | |
C1 | 0.9490 (3) | 0.30152 (14) | 0.87591 (14) | 0.0489 (4) | |
H1 | 0.9594 | 0.3783 | 0.9037 | 0.059* | |
C2 | 1.1138 (3) | 0.22543 (16) | 0.91261 (15) | 0.0547 (4) | |
H2 | 1.2353 | 0.2509 | 0.9649 | 0.066* | |
C3 | 1.1004 (3) | 0.11053 (15) | 0.87219 (15) | 0.0540 (4) | |
C4 | 0.9219 (4) | 0.07293 (16) | 0.79354 (16) | 0.0605 (5) | |
H4 | 0.9125 | −0.0038 | 0.7656 | 0.073* | |
C5 | 0.7577 (4) | 0.15083 (16) | 0.75692 (15) | 0.0591 (5) | |
H5 | 0.6382 | 0.1258 | 0.7036 | 0.071* | |
C6 | 0.7668 (3) | 0.26522 (14) | 0.79771 (13) | 0.0470 (4) | |
C7 | 0.5852 (3) | 0.34387 (15) | 0.75490 (13) | 0.0503 (4) | |
C8 | 0.3738 (3) | 0.52345 (13) | 0.80512 (13) | 0.0436 (4) | |
C9 | 0.1161 (3) | 0.60806 (14) | 0.66474 (13) | 0.0479 (4) | |
C10 | 0.1614 (4) | 0.64105 (18) | 0.56187 (15) | 0.0633 (5) | |
H10 | 0.2845 | 0.6072 | 0.5227 | 0.076* | |
C11 | 0.0228 (4) | 0.72492 (19) | 0.51686 (16) | 0.0683 (5) | |
H11 | 0.0535 | 0.7462 | 0.4470 | 0.082* | |
C12 | −0.1587 (4) | 0.77740 (16) | 0.57293 (17) | 0.0607 (5) | |
C13 | −0.2064 (4) | 0.74001 (17) | 0.67491 (17) | 0.0615 (5) | |
H13 | −0.3326 | 0.7722 | 0.7134 | 0.074* | |
C14 | −0.0711 (3) | 0.65599 (16) | 0.72124 (15) | 0.0555 (4) | |
H14 | −0.1064 | 0.6321 | 0.7899 | 0.067* | |
C15 | 1.2704 (5) | −0.07619 (18) | 0.8778 (2) | 0.0857 (7) | |
H15A | 1.1107 | −0.1161 | 0.8894 | 0.129* | |
H15B | 1.3984 | −0.1133 | 0.9161 | 0.129* | |
H15C | 1.3025 | −0.0793 | 0.8023 | 0.129* | |
C16 | −0.3010 (5) | 0.87282 (19) | 0.5254 (2) | 0.0845 (7) | |
H16A | −0.2312 | 0.9477 | 0.5537 | 0.127* | |
H16B | −0.4734 | 0.8625 | 0.5437 | 0.127* | |
H16C | −0.2887 | 0.8689 | 0.4485 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0841 (4) | 0.0489 (3) | 0.0469 (3) | 0.0265 (2) | −0.0092 (2) | −0.00611 (19) |
O1 | 0.1062 (11) | 0.0697 (9) | 0.0476 (8) | 0.0417 (8) | −0.0169 (7) | −0.0130 (6) |
O2 | 0.0776 (9) | 0.0534 (8) | 0.0967 (11) | 0.0236 (7) | −0.0202 (8) | 0.0024 (7) |
N1 | 0.0588 (8) | 0.0419 (7) | 0.0381 (7) | 0.0144 (6) | −0.0033 (6) | 0.0004 (5) |
N2 | 0.0624 (9) | 0.0470 (8) | 0.0421 (7) | 0.0160 (7) | −0.0043 (6) | −0.0006 (6) |
C1 | 0.0533 (10) | 0.0389 (8) | 0.0545 (10) | 0.0047 (7) | 0.0050 (8) | −0.0015 (7) |
C2 | 0.0508 (10) | 0.0508 (10) | 0.0621 (11) | 0.0058 (8) | −0.0047 (8) | −0.0007 (8) |
C3 | 0.0563 (10) | 0.0466 (9) | 0.0606 (11) | 0.0123 (8) | 0.0010 (8) | 0.0069 (8) |
C4 | 0.0770 (13) | 0.0406 (9) | 0.0643 (12) | 0.0146 (9) | −0.0062 (10) | −0.0051 (8) |
C5 | 0.0731 (12) | 0.0497 (10) | 0.0544 (10) | 0.0160 (9) | −0.0122 (9) | −0.0077 (8) |
C6 | 0.0566 (10) | 0.0435 (9) | 0.0418 (8) | 0.0108 (7) | 0.0033 (7) | 0.0005 (7) |
C7 | 0.0636 (10) | 0.0458 (9) | 0.0424 (9) | 0.0131 (8) | −0.0002 (8) | −0.0007 (7) |
C8 | 0.0499 (9) | 0.0390 (8) | 0.0428 (8) | 0.0068 (7) | 0.0027 (7) | 0.0040 (6) |
C9 | 0.0516 (9) | 0.0453 (9) | 0.0468 (9) | 0.0079 (7) | −0.0070 (7) | 0.0027 (7) |
C10 | 0.0678 (12) | 0.0759 (13) | 0.0487 (10) | 0.0221 (10) | −0.0011 (9) | 0.0062 (9) |
C11 | 0.0774 (13) | 0.0765 (13) | 0.0528 (11) | 0.0132 (11) | −0.0088 (10) | 0.0175 (10) |
C12 | 0.0615 (11) | 0.0501 (10) | 0.0694 (12) | 0.0063 (9) | −0.0235 (9) | 0.0040 (9) |
C13 | 0.0540 (10) | 0.0615 (11) | 0.0697 (12) | 0.0157 (9) | −0.0064 (9) | −0.0018 (9) |
C14 | 0.0524 (10) | 0.0608 (11) | 0.0544 (10) | 0.0099 (8) | 0.0013 (8) | 0.0070 (8) |
C15 | 0.0955 (17) | 0.0514 (12) | 0.113 (2) | 0.0311 (12) | −0.0112 (14) | 0.0041 (12) |
C16 | 0.0956 (17) | 0.0599 (12) | 0.0977 (17) | 0.0193 (12) | −0.0393 (14) | 0.0069 (11) |
S1—C8 | 1.6640 (16) | C5—H5 | 0.9300 |
O1—C7 | 1.225 (2) | C6—C7 | 1.479 (2) |
O2—C3 | 1.353 (2) | C9—C10 | 1.375 (3) |
O2—C15 | 1.427 (2) | C9—C14 | 1.376 (2) |
N1—C7 | 1.376 (2) | C10—C11 | 1.385 (3) |
N1—C8 | 1.385 (2) | C10—H10 | 0.9300 |
N1—H1A | 0.8600 | C11—C12 | 1.374 (3) |
N2—C8 | 1.328 (2) | C11—H11 | 0.9300 |
N2—C9 | 1.427 (2) | C12—C13 | 1.383 (3) |
N2—H2A | 0.8600 | C12—C16 | 1.511 (3) |
C1—C2 | 1.370 (2) | C13—C14 | 1.383 (2) |
C1—C6 | 1.388 (2) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.387 (3) | C15—H15A | 0.9600 |
C2—H2 | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.382 (3) | C15—H15C | 0.9600 |
C4—C5 | 1.382 (2) | C16—H16A | 0.9600 |
C4—H4 | 0.9300 | C16—H16B | 0.9600 |
C5—C6 | 1.384 (2) | C16—H16C | 0.9600 |
N2—C8—N1 | 116.22 (14) | C10—C9—C14 | 119.88 (16) |
N2—C8—S1 | 125.97 (12) | C10—C9—N2 | 117.67 (15) |
N1—C8—S1 | 117.81 (12) | C14—C9—N2 | 122.44 (15) |
C3—O2—C15 | 118.65 (16) | C9—C10—C11 | 119.70 (18) |
C7—N1—C8 | 128.64 (14) | C9—C10—H10 | 120.1 |
C7—N1—H1A | 115.7 | C11—C10—H10 | 120.1 |
C8—N1—H1A | 115.7 | C12—C11—C10 | 121.62 (18) |
C8—N2—C9 | 127.53 (14) | C12—C11—H11 | 119.2 |
C8—N2—H2A | 116.2 | C10—C11—H11 | 119.2 |
C9—N2—H2A | 116.2 | C11—C12—C13 | 117.56 (17) |
C2—C1—C6 | 120.72 (16) | C11—C12—C16 | 121.4 (2) |
C2—C1—H1 | 119.6 | C13—C12—C16 | 121.0 (2) |
C6—C1—H1 | 119.6 | C12—C13—C14 | 121.74 (18) |
C1—C2—C3 | 120.32 (17) | C12—C13—H13 | 119.1 |
C1—C2—H2 | 119.8 | C14—C13—H13 | 119.1 |
C3—C2—H2 | 119.8 | C9—C14—C13 | 119.41 (17) |
O2—C3—C4 | 125.03 (17) | C9—C14—H14 | 120.3 |
O2—C3—C2 | 115.10 (17) | C13—C14—H14 | 120.3 |
C4—C3—C2 | 119.88 (16) | O2—C15—H15A | 109.5 |
C5—C4—C3 | 119.16 (17) | O2—C15—H15B | 109.5 |
C5—C4—H4 | 120.4 | H15A—C15—H15B | 109.5 |
C3—C4—H4 | 120.4 | O2—C15—H15C | 109.5 |
C4—C5—C6 | 121.51 (17) | H15A—C15—H15C | 109.5 |
C4—C5—H5 | 119.2 | H15B—C15—H15C | 109.5 |
C6—C5—H5 | 119.2 | C12—C16—H16A | 109.5 |
C5—C6—C1 | 118.40 (16) | C12—C16—H16B | 109.5 |
C5—C6—C7 | 118.67 (16) | H16A—C16—H16B | 109.5 |
C1—C6—C7 | 122.93 (15) | C12—C16—H16C | 109.5 |
O1—C7—N1 | 122.01 (15) | H16A—C16—H16C | 109.5 |
O1—C7—C6 | 122.32 (15) | H16B—C16—H16C | 109.5 |
N1—C7—C6 | 115.68 (14) | ||
C6—C1—C2—C3 | −0.2 (3) | C1—C6—C7—N1 | −28.3 (2) |
C15—O2—C3—C4 | 1.0 (3) | C9—N2—C8—N1 | −174.53 (15) |
C15—O2—C3—C2 | −179.32 (19) | C9—N2—C8—S1 | 4.6 (3) |
C1—C2—C3—O2 | −178.90 (17) | C7—N1—C8—N2 | 1.6 (3) |
C1—C2—C3—C4 | 0.8 (3) | C7—N1—C8—S1 | −177.65 (14) |
O2—C3—C4—C5 | 179.17 (18) | C8—N2—C9—C10 | 134.9 (2) |
C2—C3—C4—C5 | −0.5 (3) | C8—N2—C9—C14 | −46.6 (3) |
C3—C4—C5—C6 | −0.4 (3) | C14—C9—C10—C11 | 1.8 (3) |
C4—C5—C6—C1 | 1.1 (3) | N2—C9—C10—C11 | −179.63 (18) |
C4—C5—C6—C7 | −179.95 (17) | C9—C10—C11—C12 | 0.6 (3) |
C2—C1—C6—C5 | −0.8 (3) | C10—C11—C12—C13 | −2.7 (3) |
C2—C1—C6—C7 | −179.69 (16) | C10—C11—C12—C16 | 177.1 (2) |
C8—N1—C7—O1 | −3.4 (3) | C11—C12—C13—C14 | 2.3 (3) |
C8—N1—C7—C6 | 176.49 (15) | C16—C12—C13—C14 | −177.45 (18) |
C5—C6—C7—O1 | −27.3 (3) | C10—C9—C14—C13 | −2.2 (3) |
C1—C6—C7—O1 | 151.62 (19) | N2—C9—C14—C13 | 179.39 (17) |
C5—C6—C7—N1 | 152.74 (17) | C12—C13—C14—C9 | 0.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.94 | 2.640 (2) | 138 |
C14—H14···S1 | 0.93 | 2.79 | 3.1980 (19) | 108 |
N1—H1A···S1i | 0.86 | 2.72 | 3.5305 (16) | 158 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O2S |
Mr | 300.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.3676 (9), 11.4763 (19), 12.447 (2) |
α, β, γ (°) | 92.505 (3), 91.692 (3), 94.138 (3) |
V (Å3) | 763.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.45 × 0.39 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.90, 0.93 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7554, 2827, 2492 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.114, 1.08 |
No. of reflections | 2827 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.16 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
S1—C8 | 1.6640 (16) | N1—C8 | 1.385 (2) |
O1—C7 | 1.225 (2) | N2—C8 | 1.328 (2) |
O2—C3 | 1.353 (2) | N2—C9 | 1.427 (2) |
N1—C7 | 1.376 (2) | ||
N2—C8—N1 | 116.22 (14) | N1—C8—S1 | 117.81 (12) |
N2—C8—S1 | 125.97 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.94 | 2.640 (2) | 138 |
C14—H14···S1 | 0.93 | 2.79 | 3.1980 (19) | 108 |
N1—H1A···S1i | 0.86 | 2.72 | 3.5305 (16) | 158 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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The title compound, (I), is isomeric and isostructural with N-(4-methoxybenzoyl)-N'-o-tolylthiourea (Yusof & Yamin, 2004). The trans–cis configuration with respect to the position of the 4-methoxybenzoyl and 4-methylphenyl groups relative to the S atom across the thiourea C8—N1 and C8—N2 bonds, respectively, is maintained.
The carbonylthiourea (S1/N1/N2/C7/O1/C8), 4-methoxybenzoyl (C1–C6/O2/C15) and 4-methylphenyl (C9–C14/C16) groups are each planar. The maximum deviation is 0.035 (1) Å for atom N1 from the mean plane in the carbonylthiourea group. The dihedral angles between the carbonylthiourea moiety and the 4-methoxyphenyl and 4-methylphenyl fragments of 27.33 (7) and 43.37 (8)°, respectively, are larger compared to those in the N-(4-methoxybenzoyl)-N'-o-tolylthiourea [15.58 (7) and 22.76 (8)°, respectively]. The inclination between the aryl fragments of 70.62 (9)° is larger than that of 7.58 (9)° in N-(4-methoxybenzoyl)-N'-o-tolylthiourea.
There are two intramolecular hydrogen bonds, viz. N2—H2A···O1 and C14—H14···S1 (Table 2), and as a result, two pseudo-six-membered rings (C8—N2—C9—C14—H14···S1 and C7—N1—C8—N2—H2A···O1) are formed. In the crystal structure, molecules are linked by intermolecular interactions, N1–H1A···S1i [symmetry code: (i) 1 − x, 1 − y, 2 − z], forming a dimer along the bc face.