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In the title compound, C
16H
16N
2O
3S, the
o-methoxyphenyl and
p-methoxybenzoyl groups are
cis and
trans, respectively, with respect to the S atom across the C—N bonds. The dihedral angle between the central NCSN thiourea fragment and the
o-methoxyphenyl group is 63.66 (8)°, while that with the
p-methoxybenzoyl group is 40.30 (7)°. The molecules are stabilized by N—H
S and C—H
O intermolecular hydrogen-bonding interactions, forming zigzag polymeric chains along the
a axis.
Supporting information
CCDC reference: 251707
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.105
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C8 .. 6.37 su
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
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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).
N-(
p-Methoxybenzoyl)-
N'-(
o-methoxyphenyl)thiourea
top
Crystal data top
C16H16N2O3S | Z = 2 |
Mr = 316.37 | F(000) = 332 |
Triclinic, P1 | Dx = 1.372 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.832 (1) Å | Cell parameters from 3149 reflections |
b = 9.151 (2) Å | θ = 1.8–26.5° |
c = 12.201 (3) Å | µ = 0.23 mm−1 |
α = 92.68 (4)° | T = 273 K |
β = 104.56 (4)° | Triangular, colourless |
γ = 113.45 (3)° | 0.49 × 0.48 × 0.40 mm |
V = 765.8 (3) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3149 independent reflections |
Radiation source: fine-focus sealed tube | 2927 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.898, Tmax = 0.915 | l = −15→15 |
8107 measured reflections | |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.2153P] where P = (Fo2 + 2Fc2)/3 |
3149 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.48384 (6) | 0.40889 (5) | 0.15572 (3) | 0.05222 (15) | |
O1 | 1.08548 (18) | 0.82102 (15) | 0.24637 (9) | 0.0580 (3) | |
O2 | 1.2894 (2) | 0.93484 (15) | −0.21987 (11) | 0.0591 (3) | |
O3 | 0.81610 (19) | 0.77415 (14) | 0.48162 (10) | 0.0564 (3) | |
N1 | 0.80446 (17) | 0.62660 (15) | 0.12521 (10) | 0.0387 (3) | |
H1A | 0.7386 | 0.5936 | 0.0539 | 0.046* | |
N2 | 0.82360 (18) | 0.58730 (15) | 0.31194 (10) | 0.0424 (3) | |
H2A | 0.9388 | 0.6637 | 0.3266 | 0.051* | |
C1 | 1.0072 (2) | 0.69176 (17) | −0.05047 (13) | 0.0396 (3) | |
H1 | 0.9167 | 0.5856 | −0.0580 | 0.048* | |
C2 | 1.0888 (2) | 0.74035 (19) | −0.13741 (13) | 0.0444 (3) | |
H2 | 1.0562 | 0.6663 | −0.2025 | 0.053* | |
C3 | 1.2201 (2) | 0.90004 (18) | −0.12825 (13) | 0.0415 (3) | |
C4 | 1.2726 (2) | 1.00955 (18) | −0.03032 (14) | 0.0435 (3) | |
H4 | 1.3601 | 1.1164 | −0.0239 | 0.052* | |
C5 | 1.1936 (2) | 0.95859 (18) | 0.05779 (13) | 0.0427 (3) | |
H5 | 1.2311 | 1.0315 | 0.1244 | 0.051* | |
C6 | 1.0591 (2) | 0.80033 (17) | 0.04867 (12) | 0.0369 (3) | |
C7 | 0.9872 (2) | 0.75296 (17) | 0.14842 (12) | 0.0396 (3) | |
C8 | 0.7146 (2) | 0.54660 (17) | 0.20346 (12) | 0.0360 (3) | |
C9 | 0.7695 (2) | 0.51734 (18) | 0.40713 (12) | 0.0393 (3) | |
C10 | 0.7723 (2) | 0.61863 (19) | 0.49694 (12) | 0.0418 (3) | |
C11 | 0.7300 (2) | 0.5566 (2) | 0.59318 (13) | 0.0510 (4) | |
H11 | 0.7278 | 0.6222 | 0.6529 | 0.061* | |
C12 | 0.6914 (3) | 0.3974 (2) | 0.59989 (15) | 0.0576 (5) | |
H12 | 0.6646 | 0.3564 | 0.6650 | 0.069* | |
C13 | 0.6916 (3) | 0.2984 (2) | 0.51239 (16) | 0.0575 (4) | |
H13 | 0.6656 | 0.1911 | 0.5183 | 0.069* | |
C14 | 0.7307 (2) | 0.3587 (2) | 0.41473 (14) | 0.0490 (4) | |
H14 | 0.7307 | 0.2920 | 0.3548 | 0.059* | |
C15 | 1.4042 (3) | 1.0982 (2) | −0.22563 (19) | 0.0648 (5) | |
H15A | 1.3268 | 1.1582 | −0.2310 | 0.097* | |
H15B | 1.4496 | 1.1024 | −0.2920 | 0.097* | |
H15C | 1.5137 | 1.1444 | −0.1578 | 0.097* | |
C16 | 0.8343 (3) | 0.8855 (2) | 0.57519 (18) | 0.0678 (5) | |
H16A | 0.7128 | 0.8504 | 0.5928 | 0.102* | |
H16B | 0.8680 | 0.9909 | 0.5541 | 0.102* | |
H16C | 0.9344 | 0.8897 | 0.6414 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0385 (2) | 0.0610 (3) | 0.0356 (2) | 0.00096 (18) | 0.00843 (16) | 0.00926 (17) |
O1 | 0.0536 (7) | 0.0570 (7) | 0.0346 (6) | −0.0025 (6) | 0.0090 (5) | 0.0044 (5) |
O2 | 0.0711 (8) | 0.0560 (7) | 0.0574 (7) | 0.0205 (6) | 0.0400 (6) | 0.0189 (6) |
O3 | 0.0704 (8) | 0.0454 (6) | 0.0481 (6) | 0.0174 (6) | 0.0213 (6) | 0.0048 (5) |
N1 | 0.0364 (6) | 0.0429 (6) | 0.0288 (6) | 0.0087 (5) | 0.0101 (5) | 0.0050 (5) |
N2 | 0.0369 (6) | 0.0465 (7) | 0.0310 (6) | 0.0050 (5) | 0.0100 (5) | 0.0060 (5) |
C1 | 0.0365 (7) | 0.0358 (7) | 0.0435 (8) | 0.0115 (6) | 0.0131 (6) | 0.0080 (6) |
C2 | 0.0467 (8) | 0.0447 (8) | 0.0404 (8) | 0.0162 (7) | 0.0163 (7) | 0.0042 (6) |
C3 | 0.0409 (8) | 0.0464 (8) | 0.0447 (8) | 0.0206 (7) | 0.0200 (6) | 0.0167 (6) |
C4 | 0.0413 (8) | 0.0363 (7) | 0.0510 (9) | 0.0118 (6) | 0.0170 (7) | 0.0126 (6) |
C5 | 0.0431 (8) | 0.0388 (7) | 0.0404 (8) | 0.0121 (6) | 0.0120 (6) | 0.0044 (6) |
C6 | 0.0334 (7) | 0.0391 (7) | 0.0372 (7) | 0.0140 (6) | 0.0105 (6) | 0.0094 (6) |
C7 | 0.0387 (7) | 0.0392 (7) | 0.0357 (7) | 0.0117 (6) | 0.0104 (6) | 0.0070 (6) |
C8 | 0.0386 (7) | 0.0368 (7) | 0.0320 (7) | 0.0140 (6) | 0.0128 (6) | 0.0048 (5) |
C9 | 0.0335 (7) | 0.0471 (8) | 0.0311 (7) | 0.0111 (6) | 0.0087 (5) | 0.0094 (6) |
C10 | 0.0358 (7) | 0.0479 (8) | 0.0345 (7) | 0.0115 (6) | 0.0087 (6) | 0.0066 (6) |
C11 | 0.0455 (9) | 0.0654 (11) | 0.0345 (8) | 0.0147 (8) | 0.0137 (6) | 0.0077 (7) |
C12 | 0.0503 (9) | 0.0736 (12) | 0.0408 (9) | 0.0154 (9) | 0.0154 (7) | 0.0248 (8) |
C13 | 0.0540 (10) | 0.0529 (10) | 0.0602 (11) | 0.0172 (8) | 0.0143 (8) | 0.0248 (8) |
C14 | 0.0486 (9) | 0.0486 (9) | 0.0466 (9) | 0.0175 (7) | 0.0135 (7) | 0.0090 (7) |
C15 | 0.0689 (12) | 0.0632 (11) | 0.0729 (13) | 0.0245 (10) | 0.0401 (10) | 0.0342 (10) |
C16 | 0.0716 (13) | 0.0558 (11) | 0.0658 (12) | 0.0194 (10) | 0.0195 (10) | −0.0090 (9) |
Geometric parameters (Å, º) top
S1—C8 | 1.6681 (15) | C5—C6 | 1.390 (2) |
O1—C7 | 1.2225 (18) | C5—H5 | 0.9300 |
O2—C3 | 1.3587 (18) | C6—C7 | 1.478 (2) |
O2—C15 | 1.421 (2) | C9—C14 | 1.373 (2) |
O3—C10 | 1.359 (2) | C9—C10 | 1.392 (2) |
O3—C16 | 1.434 (2) | C10—C11 | 1.385 (2) |
N1—C7 | 1.3838 (18) | C11—C12 | 1.376 (3) |
N1—C8 | 1.3915 (18) | C11—H11 | 0.9300 |
N1—H1A | 0.8600 | C12—C13 | 1.368 (3) |
N2—C8 | 1.3236 (18) | C12—H12 | 0.9300 |
N2—C9 | 1.4279 (18) | C13—C14 | 1.389 (2) |
N2—H2A | 0.8600 | C13—H13 | 0.9300 |
C1—C2 | 1.375 (2) | C14—H14 | 0.9300 |
C1—C6 | 1.391 (2) | C15—H15A | 0.9600 |
C1—H1 | 0.9300 | C15—H15B | 0.9600 |
C2—C3 | 1.391 (2) | C15—H15C | 0.9600 |
C2—H2 | 0.9300 | C16—H16A | 0.9600 |
C3—C4 | 1.383 (2) | C16—H16B | 0.9600 |
C4—C5 | 1.381 (2) | C16—H16C | 0.9600 |
C4—H4 | 0.9300 | | |
| | | |
C3—O2—C15 | 119.37 (14) | N1—C8—S1 | 119.03 (10) |
C10—O3—C16 | 117.73 (14) | C14—C9—C10 | 120.59 (14) |
C7—N1—C8 | 127.74 (12) | C14—C9—N2 | 121.50 (14) |
C7—N1—H1A | 116.1 | C10—C9—N2 | 117.72 (13) |
C8—N1—H1A | 116.1 | O3—C10—C11 | 124.87 (15) |
C8—N2—C9 | 126.65 (12) | O3—C10—C9 | 115.84 (13) |
C8—N2—H2A | 116.7 | C11—C10—C9 | 119.30 (15) |
C9—N2—H2A | 116.7 | C12—C11—C10 | 119.59 (16) |
C2—C1—C6 | 120.41 (13) | C12—C11—H11 | 120.2 |
C2—C1—H1 | 119.8 | C10—C11—H11 | 120.2 |
C6—C1—H1 | 119.8 | C13—C12—C11 | 121.13 (15) |
C1—C2—C3 | 120.16 (14) | C13—C12—H12 | 119.4 |
C1—C2—H2 | 119.9 | C11—C12—H12 | 119.4 |
C3—C2—H2 | 119.9 | C12—C13—C14 | 119.74 (16) |
O2—C3—C4 | 124.88 (14) | C12—C13—H13 | 120.1 |
O2—C3—C2 | 115.07 (14) | C14—C13—H13 | 120.1 |
C4—C3—C2 | 120.05 (13) | C9—C14—C13 | 119.62 (16) |
C5—C4—C3 | 119.35 (14) | C9—C14—H14 | 120.2 |
C5—C4—H4 | 120.3 | C13—C14—H14 | 120.2 |
C3—C4—H4 | 120.3 | O2—C15—H15A | 109.5 |
C4—C5—C6 | 121.16 (14) | O2—C15—H15B | 109.5 |
C4—C5—H5 | 119.4 | H15A—C15—H15B | 109.5 |
C6—C5—H5 | 119.4 | O2—C15—H15C | 109.5 |
C5—C6—C1 | 118.83 (13) | H15A—C15—H15C | 109.5 |
C5—C6—C7 | 118.05 (13) | H15B—C15—H15C | 109.5 |
C1—C6—C7 | 123.01 (13) | O3—C16—H16A | 109.5 |
O1—C7—N1 | 121.87 (13) | O3—C16—H16B | 109.5 |
O1—C7—C6 | 121.56 (13) | H16A—C16—H16B | 109.5 |
N1—C7—C6 | 116.56 (12) | O3—C16—H16C | 109.5 |
N2—C8—N1 | 115.77 (12) | H16A—C16—H16C | 109.5 |
N2—C8—S1 | 125.20 (11) | H16B—C16—H16C | 109.5 |
| | | |
C6—C1—C2—C3 | −1.8 (2) | C9—N2—C8—S1 | 3.2 (2) |
C15—O2—C3—C4 | −8.9 (2) | C7—N1—C8—N2 | −6.3 (2) |
C15—O2—C3—C2 | 171.90 (16) | C7—N1—C8—S1 | 174.12 (12) |
C1—C2—C3—O2 | −179.13 (14) | C8—N2—C9—C14 | 64.4 (2) |
C1—C2—C3—C4 | 1.6 (2) | C8—N2—C9—C10 | −120.54 (17) |
O2—C3—C4—C5 | −179.14 (14) | C16—O3—C10—C11 | 4.9 (2) |
C2—C3—C4—C5 | 0.1 (2) | C16—O3—C10—C9 | −175.61 (15) |
C3—C4—C5—C6 | −1.5 (2) | C14—C9—C10—O3 | 178.70 (14) |
C4—C5—C6—C1 | 1.2 (2) | N2—C9—C10—O3 | 3.6 (2) |
C4—C5—C6—C7 | 177.48 (14) | C14—C9—C10—C11 | −1.8 (2) |
C2—C1—C6—C5 | 0.4 (2) | N2—C9—C10—C11 | −176.83 (13) |
C2—C1—C6—C7 | −175.60 (14) | O3—C10—C11—C12 | −178.75 (16) |
C8—N1—C7—O1 | −7.8 (2) | C9—C10—C11—C12 | 1.8 (2) |
C8—N1—C7—C6 | 171.40 (13) | C10—C11—C12—C13 | −0.8 (3) |
C5—C6—C7—O1 | −27.2 (2) | C11—C12—C13—C14 | −0.2 (3) |
C1—C6—C7—O1 | 148.90 (16) | C10—C9—C14—C13 | 0.8 (2) |
C5—C6—C7—N1 | 153.60 (14) | N2—C9—C14—C13 | 175.65 (15) |
C1—C6—C7—N1 | −30.3 (2) | C12—C13—C14—C9 | 0.2 (3) |
C9—N2—C8—N1 | −176.40 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.93 | 2.630 (2) | 137 |
N1—H1A···S1i | 0.86 | 2.70 | 3.518 (2) | 159 |
C14—H14···O2ii | 0.93 | 2.52 | 3.431 (2) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z. |
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