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The 4-methoxybenzoyl and 3-(hydroxymethyl)phenyl groups in the title compound, C
16H
16N
2O
3S, are
trans and
cis, respectively, with respect to the thione group across the C—N bonds. The central carbonylthiourea moiety makes dihedral angles with the 4-methoxybenzoyl and 3-(hydroxymethyl)phenyl fragments of 33.48 (7) and 45.96 (6)°, respectively. The molecules are stabilized by intermolecular N—H
O and O—H
S hydrogen bonds to form tetramers.
Supporting information
CCDC reference: 270220
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.128
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
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-[3-(Hydroxymethyl)phenyl]-
N'-(4-methoxybenzoyl)thiourea
top
Crystal data top
C16H16N2O3S | F(000) = 1328 |
Mr = 316.37 | Dx = 1.377 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 864 reflections |
a = 17.559 (7) Å | θ = 2.1–26.5° |
b = 8.959 (4) Å | µ = 0.23 mm−1 |
c = 19.566 (8) Å | T = 298 K |
β = 97.591 (9)° | Block, colourless |
V = 3051 (2) Å3 | 0.40 × 0.29 × 0.26 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3144 independent reflections |
Radiation source: fine-focus sealed tube | 2828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 2.1° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (SABABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.915, Tmax = 0.944 | l = −24→11 |
8291 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0509P)2 + 2.0214P] where P = (Fo2 + 2Fc2)/3 |
3144 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.07962 (3) | 0.68340 (6) | 0.18596 (3) | 0.0527 (2) | |
O1 | 0.14005 (8) | 1.13145 (18) | 0.09789 (9) | 0.0599 (4) | |
O2 | −0.18566 (9) | 1.43906 (18) | 0.02016 (9) | 0.0634 (5) | |
O3 | 0.40650 (9) | 0.3484 (2) | 0.15634 (10) | 0.0695 (5) | |
H3 | 0.4198 | 0.2953 | 0.1899 | 0.104* | |
N1 | 0.06019 (9) | 0.94664 (18) | 0.12610 (9) | 0.0422 (4) | |
H1 | 0.0126 | 0.9237 | 0.1255 | 0.051* | |
N2 | 0.18627 (9) | 0.8742 (2) | 0.15135 (9) | 0.0471 (4) | |
H2 | 0.1948 | 0.9595 | 0.1337 | 0.057* | |
C1 | −0.06434 (12) | 1.1161 (2) | 0.04879 (10) | 0.0444 (5) | |
H1A | −0.0693 | 1.0132 | 0.0436 | 0.053* | |
C2 | −0.12647 (12) | 1.2065 (2) | 0.02903 (11) | 0.0468 (5) | |
H2A | −0.1729 | 1.1653 | 0.0095 | 0.056* | |
C3 | −0.11972 (12) | 1.3597 (2) | 0.03825 (11) | 0.0459 (5) | |
C4 | −0.04984 (13) | 1.4226 (2) | 0.06524 (12) | 0.0512 (5) | |
H4 | −0.0453 | 1.5253 | 0.0711 | 0.061* | |
C5 | 0.01249 (12) | 1.3312 (2) | 0.08317 (12) | 0.0493 (5) | |
H5 | 0.0597 | 1.3732 | 0.1000 | 0.059* | |
C6 | 0.00625 (11) | 1.1773 (2) | 0.07658 (10) | 0.0420 (5) | |
C7 | 0.07457 (11) | 1.0855 (2) | 0.10025 (11) | 0.0445 (5) | |
C8 | 0.11279 (11) | 0.8390 (2) | 0.15305 (10) | 0.0415 (5) | |
C9 | 0.25241 (11) | 0.7874 (2) | 0.17531 (10) | 0.0445 (5) | |
C10 | 0.31375 (12) | 0.8608 (3) | 0.21240 (12) | 0.0547 (6) | |
H10 | 0.3101 | 0.9614 | 0.2232 | 0.066* | |
C11 | 0.38078 (13) | 0.7823 (3) | 0.23320 (13) | 0.0614 (7) | |
H11 | 0.4223 | 0.8303 | 0.2584 | 0.074* | |
C12 | 0.38613 (12) | 0.6332 (3) | 0.21677 (12) | 0.0574 (6) | |
H12 | 0.4312 | 0.5813 | 0.2314 | 0.069* | |
C13 | 0.32550 (11) | 0.5602 (3) | 0.17889 (11) | 0.0478 (5) | |
C14 | 0.25829 (11) | 0.6393 (3) | 0.15805 (11) | 0.0460 (5) | |
H14 | 0.2170 | 0.5917 | 0.1323 | 0.055* | |
C15 | −0.18467 (16) | 1.5943 (3) | 0.03492 (18) | 0.0795 (9) | |
H15A | −0.1637 | 1.6101 | 0.0822 | 0.119* | |
H15B | −0.2361 | 1.6328 | 0.0271 | 0.119* | |
H15C | −0.1536 | 1.6450 | 0.0054 | 0.119* | |
C16 | 0.33029 (13) | 0.3993 (3) | 0.15844 (14) | 0.0631 (7) | |
H16A | 0.3068 | 0.3383 | 0.1909 | 0.076* | |
H16B | 0.3009 | 0.3856 | 0.1133 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0381 (3) | 0.0423 (3) | 0.0775 (4) | 0.0045 (2) | 0.0060 (2) | 0.0070 (3) |
O1 | 0.0379 (8) | 0.0573 (10) | 0.0854 (12) | 0.0051 (7) | 0.0117 (7) | 0.0184 (8) |
O2 | 0.0505 (9) | 0.0545 (10) | 0.0807 (12) | 0.0174 (7) | −0.0072 (8) | 0.0062 (8) |
O3 | 0.0497 (9) | 0.0730 (12) | 0.0895 (13) | 0.0311 (8) | 0.0233 (9) | 0.0239 (10) |
N1 | 0.0309 (8) | 0.0424 (9) | 0.0531 (10) | 0.0060 (7) | 0.0053 (7) | 0.0039 (8) |
N2 | 0.0342 (8) | 0.0473 (10) | 0.0595 (11) | 0.0054 (7) | 0.0052 (7) | 0.0069 (8) |
C1 | 0.0495 (11) | 0.0407 (11) | 0.0426 (11) | 0.0052 (9) | 0.0043 (9) | −0.0013 (9) |
C2 | 0.0430 (11) | 0.0505 (12) | 0.0448 (11) | 0.0036 (9) | −0.0020 (9) | −0.0001 (9) |
C3 | 0.0429 (11) | 0.0472 (12) | 0.0471 (11) | 0.0105 (9) | 0.0031 (9) | 0.0077 (9) |
C4 | 0.0515 (12) | 0.0396 (11) | 0.0619 (14) | 0.0055 (9) | 0.0047 (10) | 0.0031 (10) |
C5 | 0.0409 (11) | 0.0471 (12) | 0.0590 (13) | −0.0020 (9) | 0.0035 (9) | 0.0035 (10) |
C6 | 0.0404 (10) | 0.0456 (11) | 0.0406 (10) | 0.0059 (8) | 0.0079 (8) | 0.0031 (9) |
C7 | 0.0401 (11) | 0.0474 (12) | 0.0466 (11) | 0.0066 (9) | 0.0076 (8) | 0.0017 (9) |
C8 | 0.0359 (10) | 0.0437 (11) | 0.0449 (11) | 0.0060 (8) | 0.0048 (8) | −0.0048 (9) |
C9 | 0.0321 (9) | 0.0571 (13) | 0.0446 (11) | 0.0086 (9) | 0.0064 (8) | 0.0030 (9) |
C10 | 0.0410 (11) | 0.0639 (14) | 0.0587 (13) | 0.0011 (10) | 0.0050 (10) | −0.0058 (11) |
C11 | 0.0375 (11) | 0.0877 (19) | 0.0559 (14) | −0.0004 (11) | −0.0050 (10) | −0.0090 (13) |
C12 | 0.0342 (11) | 0.0879 (18) | 0.0490 (13) | 0.0173 (11) | 0.0012 (9) | 0.0054 (12) |
C13 | 0.0351 (10) | 0.0644 (14) | 0.0447 (11) | 0.0131 (9) | 0.0079 (8) | 0.0041 (10) |
C14 | 0.0315 (9) | 0.0595 (13) | 0.0465 (11) | 0.0069 (9) | 0.0039 (8) | −0.0007 (10) |
C15 | 0.0661 (17) | 0.0510 (15) | 0.122 (3) | 0.0218 (13) | 0.0146 (16) | 0.0140 (15) |
C16 | 0.0426 (12) | 0.0701 (16) | 0.0768 (17) | 0.0214 (11) | 0.0085 (11) | −0.0024 (13) |
Geometric parameters (Å, º) top
S1—C8 | 1.672 (2) | C5—C6 | 1.388 (3) |
O1—C7 | 1.228 (2) | C5—H5 | 0.9300 |
O2—C3 | 1.365 (2) | C6—C7 | 1.478 (3) |
O2—C15 | 1.420 (3) | C9—C14 | 1.377 (3) |
O3—C16 | 1.419 (3) | C9—C10 | 1.383 (3) |
O3—H3 | 0.8200 | C10—C11 | 1.385 (3) |
N1—C7 | 1.378 (3) | C10—H10 | 0.9300 |
N1—C8 | 1.390 (2) | C11—C12 | 1.380 (4) |
N1—H1 | 0.8600 | C11—H11 | 0.9300 |
N2—C8 | 1.333 (3) | C12—C13 | 1.379 (3) |
N2—C9 | 1.425 (2) | C12—H12 | 0.9300 |
N2—H2 | 0.8600 | C13—C14 | 1.391 (3) |
C1—C2 | 1.373 (3) | C13—C16 | 1.501 (3) |
C1—C6 | 1.398 (3) | C14—H14 | 0.9300 |
C1—H1A | 0.9300 | C15—H15A | 0.9600 |
C2—C3 | 1.387 (3) | C15—H15B | 0.9600 |
C2—H2A | 0.9300 | C15—H15C | 0.9600 |
C3—C4 | 1.389 (3) | C16—H16A | 0.9700 |
C4—C5 | 1.375 (3) | C16—H16B | 0.9700 |
C4—H4 | 0.9300 | | |
| | | |
C3—O2—C15 | 118.04 (19) | N1—C8—S1 | 118.47 (15) |
C16—O3—H3 | 109.5 | C14—C9—C10 | 120.57 (19) |
C7—N1—C8 | 128.35 (17) | C14—C9—N2 | 122.00 (19) |
C7—N1—H1 | 115.8 | C10—C9—N2 | 117.2 (2) |
C8—N1—H1 | 115.8 | C9—C10—C11 | 119.0 (2) |
C8—N2—C9 | 127.75 (19) | C9—C10—H10 | 120.5 |
C8—N2—H2 | 116.1 | C11—C10—H10 | 120.5 |
C9—N2—H2 | 116.1 | C12—C11—C10 | 120.3 (2) |
C2—C1—C6 | 120.6 (2) | C12—C11—H11 | 119.8 |
C2—C1—H1A | 119.7 | C10—C11—H11 | 119.8 |
C6—C1—H1A | 119.7 | C13—C12—C11 | 120.8 (2) |
C1—C2—C3 | 119.7 (2) | C13—C12—H12 | 119.6 |
C1—C2—H2A | 120.1 | C11—C12—H12 | 119.6 |
C3—C2—H2A | 120.1 | C12—C13—C14 | 118.7 (2) |
O2—C3—C2 | 115.24 (19) | C12—C13—C16 | 122.16 (19) |
O2—C3—C4 | 124.3 (2) | C14—C13—C16 | 119.1 (2) |
C2—C3—C4 | 120.41 (19) | C9—C14—C13 | 120.5 (2) |
C5—C4—C3 | 119.3 (2) | C9—C14—H14 | 119.7 |
C5—C4—H4 | 120.4 | C13—C14—H14 | 119.7 |
C3—C4—H4 | 120.4 | O2—C15—H15A | 109.5 |
C4—C5—C6 | 121.2 (2) | 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 | 118.73 (18) | H15A—C15—H15C | 109.5 |
C5—C6—C7 | 118.24 (19) | H15B—C15—H15C | 109.5 |
C1—C6—C7 | 123.03 (19) | O3—C16—C13 | 113.7 (2) |
O1—C7—N1 | 122.29 (18) | O3—C16—H16A | 108.8 |
O1—C7—C6 | 121.79 (19) | C13—C16—H16A | 108.8 |
N1—C7—C6 | 115.91 (18) | O3—C16—H16B | 108.8 |
N2—C8—N1 | 115.02 (18) | C13—C16—H16B | 108.8 |
N2—C8—S1 | 126.48 (15) | H16A—C16—H16B | 107.7 |
| | | |
C6—C1—C2—C3 | −1.6 (3) | C9—N2—C8—N1 | 179.67 (19) |
C15—O2—C3—C2 | 173.6 (2) | C9—N2—C8—S1 | 1.6 (3) |
C15—O2—C3—C4 | −5.3 (3) | C7—N1—C8—N2 | −2.3 (3) |
C1—C2—C3—O2 | −176.87 (19) | C7—N1—C8—S1 | 175.95 (16) |
C1—C2—C3—C4 | 2.1 (3) | C8—N2—C9—C14 | 48.7 (3) |
O2—C3—C4—C5 | 178.5 (2) | C8—N2—C9—C10 | −136.3 (2) |
C2—C3—C4—C5 | −0.4 (3) | C14—C9—C10—C11 | −1.3 (3) |
C3—C4—C5—C6 | −1.8 (3) | N2—C9—C10—C11 | −176.3 (2) |
C4—C5—C6—C1 | 2.3 (3) | C9—C10—C11—C12 | 0.3 (4) |
C4—C5—C6—C7 | −176.8 (2) | C10—C11—C12—C13 | 0.7 (4) |
C2—C1—C6—C5 | −0.6 (3) | C11—C12—C13—C14 | −0.6 (3) |
C2—C1—C6—C7 | 178.52 (19) | C11—C12—C13—C16 | 178.2 (2) |
C8—N1—C7—O1 | 0.4 (3) | C10—C9—C14—C13 | 1.3 (3) |
C8—N1—C7—C6 | −178.57 (18) | N2—C9—C14—C13 | 176.12 (19) |
C5—C6—C7—O1 | −31.0 (3) | C12—C13—C14—C9 | −0.4 (3) |
C1—C6—C7—O1 | 149.9 (2) | C16—C13—C14—C9 | −179.3 (2) |
C5—C6—C7—N1 | 147.9 (2) | C12—C13—C16—O3 | −23.6 (3) |
C1—C6—C7—N1 | −31.2 (3) | C14—C13—C16—O3 | 155.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.90 | 2.615 (3) | 140 |
C14—H14···S1 | 0.93 | 2.87 | 3.279 (3) | 108 |
N1—H1···O3i | 0.86 | 2.14 | 2.971 (3) | 162 |
O3—H3···S1ii | 0.82 | 2.63 | 3.401 (3) | 158 |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1/2, y−1/2, −z+1/2. |
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