Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The benzoyl and methoxybenzene groups in the title compound, C16H16N2O2S, are cis and trans, respectively, with respect to the C=S bond. The crystal packing is characterized by N—H...O and N–H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010185/fl2106sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010185/fl2106Isup2.hkl
Contains datablock I

CCDC reference: 642986

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.090
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 900 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 5.49 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

3-(3-Methoxyphenyl)-1-(2-methylbenzoyl)thiourea top
Crystal data top
C16H16N2O2SZ = 2
Mr = 300.37F(000) = 316
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2912 (7) ÅCell parameters from 7832 reflections
b = 10.3513 (12) Åθ = 3.6–25.9°
c = 11.5578 (13) ŵ = 0.22 mm1
α = 94.835 (9)°T = 173 K
β = 92.621 (9)°Block, colourless
γ = 97.322 (9)°0.42 × 0.39 × 0.35 mm
V = 742.66 (15) Å3
Data collection top
Stoe IPDSII two-circle
diffractometer
2783 independent reflections
Radiation source: fine-focus sealed tube2515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
[MULABS (Spek, 2003; Blessing, 1995)]
h = 76
Tmin = 0.912, Tmax = 0.926k = 1212
8099 measured reflectionsl = 1413
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2444P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2783 reflectionsΔρmax = 0.26 e Å3
201 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (4)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.29018 (18)0.38389 (11)0.78139 (10)0.0216 (3)
H10.357 (3)0.4293 (17)0.8428 (16)0.033 (4)*
C10.3850 (2)0.40608 (12)0.68210 (11)0.0211 (3)
S10.30086 (7)0.34230 (4)0.54723 (3)0.03518 (15)
N20.57260 (18)0.49617 (11)0.69432 (10)0.0225 (3)
H20.626 (3)0.5169 (16)0.6286 (15)0.030 (4)*
C20.6596 (2)0.57529 (12)0.79242 (11)0.0211 (3)
O20.58229 (16)0.56880 (10)0.88820 (8)0.0273 (2)
C110.0860 (2)0.31383 (12)0.79998 (11)0.0203 (3)
C120.0209 (2)0.21339 (13)0.72206 (12)0.0239 (3)
H120.04170.18620.65230.029*
C130.2227 (2)0.15378 (13)0.74938 (12)0.0247 (3)
C140.3154 (2)0.19272 (14)0.85180 (13)0.0276 (3)
H140.45370.15280.86840.033*
C150.2038 (2)0.29019 (14)0.92913 (13)0.0289 (3)
H150.26480.31590.99980.035*
C160.0023 (2)0.35079 (13)0.90392 (12)0.0246 (3)
H160.07430.41700.95750.030*
O170.34092 (17)0.05380 (10)0.67932 (10)0.0351 (3)
C170.2465 (3)0.00683 (16)0.57624 (14)0.0360 (4)
H17A0.22130.07760.52530.054*
H17B0.34390.06590.53540.054*
H17C0.10980.02340.59740.054*
C210.8539 (2)0.66829 (13)0.77154 (11)0.0218 (3)
C220.8874 (2)0.79541 (13)0.83018 (12)0.0251 (3)
C231.0717 (3)0.87745 (15)0.80624 (13)0.0325 (4)
H231.09720.96370.84370.039*
C241.2186 (2)0.83673 (16)0.72939 (14)0.0359 (4)
H241.34220.89490.71540.043*
C251.1854 (2)0.71155 (16)0.67303 (14)0.0332 (4)
H251.28580.68340.62060.040*
C261.0027 (2)0.62745 (14)0.69440 (12)0.0265 (3)
H260.97900.54150.65620.032*
C270.7345 (3)0.84678 (14)0.91435 (13)0.0320 (3)
H27A0.75280.80980.98890.048*
H27B0.58650.82160.88260.048*
H27C0.76480.94230.92620.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0191 (6)0.0226 (6)0.0207 (6)0.0061 (5)0.0013 (5)0.0011 (4)
C10.0198 (7)0.0178 (6)0.0243 (7)0.0034 (5)0.0032 (5)0.0019 (5)
S10.0432 (3)0.0340 (2)0.0208 (2)0.02184 (17)0.00566 (15)0.00256 (15)
N20.0205 (6)0.0230 (6)0.0215 (6)0.0068 (5)0.0050 (5)0.0009 (5)
C20.0187 (7)0.0202 (6)0.0235 (7)0.0014 (5)0.0005 (5)0.0032 (5)
O20.0264 (5)0.0311 (5)0.0215 (5)0.0083 (4)0.0031 (4)0.0019 (4)
C110.0182 (6)0.0194 (6)0.0234 (7)0.0007 (5)0.0026 (5)0.0064 (5)
C120.0227 (7)0.0233 (7)0.0243 (7)0.0037 (5)0.0065 (5)0.0009 (5)
C130.0217 (7)0.0217 (6)0.0294 (7)0.0040 (5)0.0035 (5)0.0030 (5)
C140.0204 (7)0.0266 (7)0.0359 (8)0.0015 (6)0.0100 (6)0.0060 (6)
C150.0298 (8)0.0286 (7)0.0292 (7)0.0030 (6)0.0125 (6)0.0038 (6)
C160.0261 (7)0.0229 (6)0.0237 (7)0.0017 (5)0.0034 (5)0.0014 (5)
O170.0274 (6)0.0331 (6)0.0387 (6)0.0147 (4)0.0088 (5)0.0074 (5)
C170.0340 (8)0.0359 (8)0.0327 (8)0.0090 (7)0.0021 (6)0.0073 (7)
C210.0181 (7)0.0235 (6)0.0223 (7)0.0035 (5)0.0025 (5)0.0055 (5)
C220.0262 (7)0.0240 (7)0.0234 (7)0.0035 (6)0.0053 (5)0.0057 (5)
C230.0342 (8)0.0268 (7)0.0323 (8)0.0115 (6)0.0088 (6)0.0073 (6)
C240.0235 (8)0.0426 (9)0.0384 (9)0.0147 (6)0.0057 (6)0.0176 (7)
C250.0186 (7)0.0457 (9)0.0354 (8)0.0015 (6)0.0020 (6)0.0134 (7)
C260.0201 (7)0.0298 (7)0.0289 (7)0.0010 (6)0.0004 (5)0.0063 (6)
C270.0392 (9)0.0251 (7)0.0300 (8)0.0008 (6)0.0005 (6)0.0002 (6)
Geometric parameters (Å, º) top
N1—C11.3409 (17)C16—H160.9500
N1—C111.4270 (16)O17—C171.4315 (19)
N1—H10.874 (18)C17—H17A0.9800
C1—N21.4016 (17)C17—H17B0.9800
C1—S11.6757 (14)C17—H17C0.9800
N2—C21.3886 (17)C21—C261.401 (2)
N2—H20.877 (18)C21—C221.4146 (19)
C2—O21.2327 (16)C22—C231.400 (2)
C2—C211.4987 (17)C22—C271.511 (2)
C11—C161.3913 (19)C23—C241.390 (2)
C11—C121.3974 (19)C23—H230.9500
C12—C131.4007 (19)C24—C251.387 (2)
C12—H120.9500C24—H240.9500
C13—O171.3738 (17)C25—C261.395 (2)
C13—C141.395 (2)C25—H250.9500
C14—C151.386 (2)C26—H260.9500
C14—H140.9500C27—H27A0.9800
C15—C161.395 (2)C27—H27B0.9800
C15—H150.9500C27—H27C0.9800
C1—N1—C11130.17 (12)O17—C17—H17A109.5
C1—N1—H1113.7 (11)O17—C17—H17B109.5
C11—N1—H1115.5 (11)H17A—C17—H17B109.5
N1—C1—N2115.07 (12)O17—C17—H17C109.5
N1—C1—S1127.51 (10)H17A—C17—H17C109.5
N2—C1—S1117.39 (10)H17B—C17—H17C109.5
C2—N2—C1128.73 (11)C26—C21—C22120.50 (12)
C2—N2—H2115.1 (11)C26—C21—C2119.30 (12)
C1—N2—H2114.8 (11)C22—C21—C2120.20 (12)
O2—C2—N2122.40 (12)C23—C22—C21117.22 (14)
O2—C2—C21123.30 (12)C23—C22—C27119.09 (13)
N2—C2—C21114.30 (11)C21—C22—C27123.68 (13)
C16—C11—C12120.90 (12)C24—C23—C22122.09 (14)
C16—C11—N1115.28 (12)C24—C23—H23119.0
C12—C11—N1123.81 (12)C22—C23—H23119.0
C11—C12—C13118.31 (13)C25—C24—C23120.30 (13)
C11—C12—H12120.8C25—C24—H24119.8
C13—C12—H12120.8C23—C24—H24119.8
O17—C13—C14115.71 (12)C24—C25—C26119.10 (15)
O17—C13—C12123.09 (13)C24—C25—H25120.4
C14—C13—C12121.20 (13)C26—C25—H25120.4
C15—C14—C13119.41 (13)C25—C26—C21120.77 (14)
C15—C14—H14120.3C25—C26—H26119.6
C13—C14—H14120.3C21—C26—H26119.6
C14—C15—C16120.40 (13)C22—C27—H27A109.5
C14—C15—H15119.8C22—C27—H27B109.5
C16—C15—H15119.8H27A—C27—H27B109.5
C11—C16—C15119.73 (13)C22—C27—H27C109.5
C11—C16—H16120.1H27A—C27—H27C109.5
C15—C16—H16120.1H27B—C27—H27C109.5
C13—O17—C17117.32 (11)
C11—N1—C1—N2170.46 (12)C14—C13—O17—C17177.03 (13)
C11—N1—C1—S17.6 (2)C12—C13—O17—C172.4 (2)
N1—C1—N2—C27.7 (2)O2—C2—C21—C26142.62 (14)
S1—C1—N2—C2170.51 (11)N2—C2—C21—C2637.36 (17)
C1—N2—C2—O24.7 (2)O2—C2—C21—C2236.71 (19)
C1—N2—C2—C21175.29 (12)N2—C2—C21—C22143.30 (13)
C1—N1—C11—C16155.10 (13)C26—C21—C22—C230.95 (19)
C1—N1—C11—C1225.8 (2)C2—C21—C22—C23179.73 (12)
C16—C11—C12—C132.1 (2)C26—C21—C22—C27179.86 (13)
N1—C11—C12—C13178.84 (12)C2—C21—C22—C270.8 (2)
C11—C12—C13—O17179.64 (13)C21—C22—C23—C240.7 (2)
C11—C12—C13—C140.3 (2)C27—C22—C23—C24179.70 (13)
O17—C13—C14—C15178.00 (13)C22—C23—C24—C250.2 (2)
C12—C13—C14—C151.4 (2)C23—C24—C25—C260.1 (2)
C13—C14—C15—C161.3 (2)C24—C25—C26—C210.1 (2)
C12—C11—C16—C152.3 (2)C22—C21—C26—C250.6 (2)
N1—C11—C16—C15178.59 (12)C2—C21—C26—C25179.97 (12)
C14—C15—C16—C110.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.874 (18)1.913 (18)2.6575 (15)142.0 (16)
N2—H2···S1i0.877 (18)2.623 (18)3.4459 (13)156.7 (14)
Symmetry code: (i) x+1, y+1, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds