organic compounds
The 4-methoxybenzoyl and 3-(hydroxymethyl)phenyl groups in the title compound, C16H16N2O3S, 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—HO and O—HS hydrogen bonds to form tetramers.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007853/ac6161sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007853/ac6161Isup2.hkl |
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
Computing details top
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. |