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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—H...O and O—H...S hydrogen bonds to form tetramers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007853/ac6161sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007853/ac6161Isup2.hkl
Contains datablock I

CCDC reference: 270220

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C16H16N2O3SF(000) = 1328
Mr = 316.37Dx = 1.377 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 864 reflections
a = 17.559 (7) Åθ = 2.1–26.5°
b = 8.959 (4) ŵ = 0.23 mm1
c = 19.566 (8) ÅT = 298 K
β = 97.591 (9)°Block, colourless
V = 3051 (2) Å30.40 × 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 tube2828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 83.66 pixels mm-1θmax = 26.5°, θmin = 2.1°
ω scansh = 2222
Absorption correction: multi-scan
(SABABS; Sheldrick, 1996)
k = 1111
Tmin = 0.915, Tmax = 0.944l = 2411
8291 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-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 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.26 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.07962 (3)0.68340 (6)0.18596 (3)0.0527 (2)
O10.14005 (8)1.13145 (18)0.09789 (9)0.0599 (4)
O20.18566 (9)1.43906 (18)0.02016 (9)0.0634 (5)
O30.40650 (9)0.3484 (2)0.15634 (10)0.0695 (5)
H30.41980.29530.18990.104*
N10.06019 (9)0.94664 (18)0.12610 (9)0.0422 (4)
H10.01260.92370.12550.051*
N20.18627 (9)0.8742 (2)0.15135 (9)0.0471 (4)
H20.19480.95950.13370.057*
C10.06434 (12)1.1161 (2)0.04879 (10)0.0444 (5)
H1A0.06931.01320.04360.053*
C20.12647 (12)1.2065 (2)0.02903 (11)0.0468 (5)
H2A0.17291.16530.00950.056*
C30.11972 (12)1.3597 (2)0.03825 (11)0.0459 (5)
C40.04984 (13)1.4226 (2)0.06524 (12)0.0512 (5)
H40.04531.52530.07110.061*
C50.01249 (12)1.3312 (2)0.08317 (12)0.0493 (5)
H50.05971.37320.10000.059*
C60.00625 (11)1.1773 (2)0.07658 (10)0.0420 (5)
C70.07457 (11)1.0855 (2)0.10025 (11)0.0445 (5)
C80.11279 (11)0.8390 (2)0.15305 (10)0.0415 (5)
C90.25241 (11)0.7874 (2)0.17531 (10)0.0445 (5)
C100.31375 (12)0.8608 (3)0.21240 (12)0.0547 (6)
H100.31010.96140.22320.066*
C110.38078 (13)0.7823 (3)0.23320 (13)0.0614 (7)
H110.42230.83030.25840.074*
C120.38613 (12)0.6332 (3)0.21677 (12)0.0574 (6)
H120.43120.58130.23140.069*
C130.32550 (11)0.5602 (3)0.17889 (11)0.0478 (5)
C140.25829 (11)0.6393 (3)0.15805 (11)0.0460 (5)
H140.21700.59170.13230.055*
C150.18467 (16)1.5943 (3)0.03492 (18)0.0795 (9)
H15A0.16371.61010.08220.119*
H15B0.23611.63280.02710.119*
H15C0.15361.64500.00540.119*
C160.33029 (13)0.3993 (3)0.15844 (14)0.0631 (7)
H16A0.30680.33830.19090.076*
H16B0.30090.38560.11330.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0381 (3)0.0423 (3)0.0775 (4)0.0045 (2)0.0060 (2)0.0070 (3)
O10.0379 (8)0.0573 (10)0.0854 (12)0.0051 (7)0.0117 (7)0.0184 (8)
O20.0505 (9)0.0545 (10)0.0807 (12)0.0174 (7)0.0072 (8)0.0062 (8)
O30.0497 (9)0.0730 (12)0.0895 (13)0.0311 (8)0.0233 (9)0.0239 (10)
N10.0309 (8)0.0424 (9)0.0531 (10)0.0060 (7)0.0053 (7)0.0039 (8)
N20.0342 (8)0.0473 (10)0.0595 (11)0.0054 (7)0.0052 (7)0.0069 (8)
C10.0495 (11)0.0407 (11)0.0426 (11)0.0052 (9)0.0043 (9)0.0013 (9)
C20.0430 (11)0.0505 (12)0.0448 (11)0.0036 (9)0.0020 (9)0.0001 (9)
C30.0429 (11)0.0472 (12)0.0471 (11)0.0105 (9)0.0031 (9)0.0077 (9)
C40.0515 (12)0.0396 (11)0.0619 (14)0.0055 (9)0.0047 (10)0.0031 (10)
C50.0409 (11)0.0471 (12)0.0590 (13)0.0020 (9)0.0035 (9)0.0035 (10)
C60.0404 (10)0.0456 (11)0.0406 (10)0.0059 (8)0.0079 (8)0.0031 (9)
C70.0401 (11)0.0474 (12)0.0466 (11)0.0066 (9)0.0076 (8)0.0017 (9)
C80.0359 (10)0.0437 (11)0.0449 (11)0.0060 (8)0.0048 (8)0.0048 (9)
C90.0321 (9)0.0571 (13)0.0446 (11)0.0086 (9)0.0064 (8)0.0030 (9)
C100.0410 (11)0.0639 (14)0.0587 (13)0.0011 (10)0.0050 (10)0.0058 (11)
C110.0375 (11)0.0877 (19)0.0559 (14)0.0004 (11)0.0050 (10)0.0090 (13)
C120.0342 (11)0.0879 (18)0.0490 (13)0.0173 (11)0.0012 (9)0.0054 (12)
C130.0351 (10)0.0644 (14)0.0447 (11)0.0131 (9)0.0079 (8)0.0041 (10)
C140.0315 (9)0.0595 (13)0.0465 (11)0.0069 (9)0.0039 (8)0.0007 (10)
C150.0661 (17)0.0510 (15)0.122 (3)0.0218 (13)0.0146 (16)0.0140 (15)
C160.0426 (12)0.0701 (16)0.0768 (17)0.0214 (11)0.0085 (11)0.0024 (13)
Geometric parameters (Å, º) top
S1—C81.672 (2)C5—C61.388 (3)
O1—C71.228 (2)C5—H50.9300
O2—C31.365 (2)C6—C71.478 (3)
O2—C151.420 (3)C9—C141.377 (3)
O3—C161.419 (3)C9—C101.383 (3)
O3—H30.8200C10—C111.385 (3)
N1—C71.378 (3)C10—H100.9300
N1—C81.390 (2)C11—C121.380 (4)
N1—H10.8600C11—H110.9300
N2—C81.333 (3)C12—C131.379 (3)
N2—C91.425 (2)C12—H120.9300
N2—H20.8600C13—C141.391 (3)
C1—C21.373 (3)C13—C161.501 (3)
C1—C61.398 (3)C14—H140.9300
C1—H1A0.9300C15—H15A0.9600
C2—C31.387 (3)C15—H15B0.9600
C2—H2A0.9300C15—H15C0.9600
C3—C41.389 (3)C16—H16A0.9700
C4—C51.375 (3)C16—H16B0.9700
C4—H40.9300
C3—O2—C15118.04 (19)N1—C8—S1118.47 (15)
C16—O3—H3109.5C14—C9—C10120.57 (19)
C7—N1—C8128.35 (17)C14—C9—N2122.00 (19)
C7—N1—H1115.8C10—C9—N2117.2 (2)
C8—N1—H1115.8C9—C10—C11119.0 (2)
C8—N2—C9127.75 (19)C9—C10—H10120.5
C8—N2—H2116.1C11—C10—H10120.5
C9—N2—H2116.1C12—C11—C10120.3 (2)
C2—C1—C6120.6 (2)C12—C11—H11119.8
C2—C1—H1A119.7C10—C11—H11119.8
C6—C1—H1A119.7C13—C12—C11120.8 (2)
C1—C2—C3119.7 (2)C13—C12—H12119.6
C1—C2—H2A120.1C11—C12—H12119.6
C3—C2—H2A120.1C12—C13—C14118.7 (2)
O2—C3—C2115.24 (19)C12—C13—C16122.16 (19)
O2—C3—C4124.3 (2)C14—C13—C16119.1 (2)
C2—C3—C4120.41 (19)C9—C14—C13120.5 (2)
C5—C4—C3119.3 (2)C9—C14—H14119.7
C5—C4—H4120.4C13—C14—H14119.7
C3—C4—H4120.4O2—C15—H15A109.5
C4—C5—C6121.2 (2)O2—C15—H15B109.5
C4—C5—H5119.4H15A—C15—H15B109.5
C6—C5—H5119.4O2—C15—H15C109.5
C5—C6—C1118.73 (18)H15A—C15—H15C109.5
C5—C6—C7118.24 (19)H15B—C15—H15C109.5
C1—C6—C7123.03 (19)O3—C16—C13113.7 (2)
O1—C7—N1122.29 (18)O3—C16—H16A108.8
O1—C7—C6121.79 (19)C13—C16—H16A108.8
N1—C7—C6115.91 (18)O3—C16—H16B108.8
N2—C8—N1115.02 (18)C13—C16—H16B108.8
N2—C8—S1126.48 (15)H16A—C16—H16B107.7
C6—C1—C2—C31.6 (3)C9—N2—C8—N1179.67 (19)
C15—O2—C3—C2173.6 (2)C9—N2—C8—S11.6 (3)
C15—O2—C3—C45.3 (3)C7—N1—C8—N22.3 (3)
C1—C2—C3—O2176.87 (19)C7—N1—C8—S1175.95 (16)
C1—C2—C3—C42.1 (3)C8—N2—C9—C1448.7 (3)
O2—C3—C4—C5178.5 (2)C8—N2—C9—C10136.3 (2)
C2—C3—C4—C50.4 (3)C14—C9—C10—C111.3 (3)
C3—C4—C5—C61.8 (3)N2—C9—C10—C11176.3 (2)
C4—C5—C6—C12.3 (3)C9—C10—C11—C120.3 (4)
C4—C5—C6—C7176.8 (2)C10—C11—C12—C130.7 (4)
C2—C1—C6—C50.6 (3)C11—C12—C13—C140.6 (3)
C2—C1—C6—C7178.52 (19)C11—C12—C13—C16178.2 (2)
C8—N1—C7—O10.4 (3)C10—C9—C14—C131.3 (3)
C8—N1—C7—C6178.57 (18)N2—C9—C14—C13176.12 (19)
C5—C6—C7—O131.0 (3)C12—C13—C14—C90.4 (3)
C1—C6—C7—O1149.9 (2)C16—C13—C14—C9179.3 (2)
C5—C6—C7—N1147.9 (2)C12—C13—C16—O323.6 (3)
C1—C6—C7—N131.2 (3)C14—C13—C16—O3155.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.902.615 (3)140
C14—H14···S10.932.873.279 (3)108
N1—H1···O3i0.862.142.971 (3)162
O3—H3···S1ii0.822.633.401 (3)158
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1/2.
 

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