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In the title compound C15H14N2OS, centrosymmetric dimers are formed via inter­molecular N—H...S hydrogen bonds. The dimeric units are linked by a weak inter­molecular C—H...S hydrogen bond, forming infinite chains along [010]. Additionally, unprecedented C—H...π inter­actions, involving the benzoyl group of the thio­urea group as donor–acceptor, connect parallel chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031928/xu2109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031928/xu2109Isup2.hkl
Contains datablock I

CCDC reference: 621555

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.052
  • wR factor = 0.199
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 0 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 1 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: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(Benzylaminothiocarbonyl)benzamide top
Crystal data top
C15H14N2OSF(000) = 1136
Mr = 270.35Dx = 1.342 Mg m3
Monoclinic, C2/cMelting point = 397–398 K
Hall symbol: -C 2ycCu Kα radiation, λ = 1.54180 Å
a = 30.560 (7) ÅCell parameters from 25 reflections
b = 6.112 (2) Åθ = 14.8–46.6°
c = 17.364 (4) ŵ = 2.09 mm1
β = 124.40 (2)°T = 297 K
V = 2676.1 (14) Å3Prism, colourless
Z = 80.35 × 0.25 × 0.15 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2125 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 67.9°, θmin = 3.5°
non–profiled ω/2θ scansh = 3630
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.518, Tmax = 0.730l = 020
2569 measured reflections2 standard reflections every 120 min
2439 independent reflections intensity decay: 1%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1204P)2 + 2.5013P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.052(Δ/σ)max < 0.001
wR(F2) = 0.199Δρmax = 0.59 e Å3
S = 1.15Δρmin = 0.38 e Å3
2439 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
173 parametersExtinction coefficient: 0.0045 (5)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.08960 (9)0.9770 (4)0.05564 (16)0.0494 (6)
H10.07521.08360.01670.059*
C20.06464 (10)0.7880 (5)0.03078 (17)0.0420 (6)
N30.01820 (8)0.7737 (4)0.05851 (15)0.0477 (6)
H30.00120.65190.07250.057*
C40.00367 (11)0.9316 (5)0.12683 (19)0.0473 (7)
S50.08431 (3)0.56316 (12)0.09774 (5)0.0559 (3)
O60.01307 (9)1.1177 (4)0.11381 (15)0.0632 (6)
C70.04922 (10)0.8561 (5)0.22074 (18)0.0472 (7)
C80.05384 (12)0.6455 (6)0.2528 (2)0.0548 (7)
H80.03010.53860.21290.066*
C90.09361 (15)0.5921 (7)0.3441 (2)0.0706 (10)
H90.09590.45130.36640.085*
C100.12985 (14)0.7500 (7)0.4017 (2)0.0729 (10)
H100.15660.71530.46310.088*
C110.12686 (15)0.9558 (8)0.3694 (2)0.0757 (11)
H110.15231.0590.40820.091*
C120.08610 (12)1.0132 (6)0.2791 (2)0.0588 (8)
H120.08351.15540.25780.071*
C130.13974 (10)1.0191 (5)0.14400 (18)0.0484 (7)
H13A0.14710.90040.18680.058*
H13B0.13671.15280.17080.058*
C140.18548 (10)1.0409 (5)0.13401 (17)0.0447 (6)
C150.22077 (11)0.8693 (6)0.1590 (2)0.0558 (7)
H150.21590.73830.18050.067*
C160.26362 (13)0.8943 (7)0.1518 (2)0.0696 (10)
H160.28730.77940.16820.083*
C170.27098 (13)1.0864 (7)0.1208 (2)0.0708 (10)
H170.29981.10180.11640.085*
C180.23634 (13)1.2574 (6)0.0959 (2)0.0638 (9)
H180.24161.38780.07460.077*
C190.19353 (12)1.2345 (5)0.1026 (2)0.0522 (7)
H190.171.35020.08580.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0390 (12)0.0522 (13)0.0465 (12)0.0025 (10)0.0178 (10)0.0057 (10)
C20.0341 (12)0.0497 (14)0.0413 (13)0.0016 (10)0.0206 (10)0.0020 (11)
N30.0370 (11)0.0540 (13)0.0419 (11)0.0061 (9)0.0161 (10)0.0054 (10)
C40.0411 (14)0.0550 (17)0.0471 (14)0.0027 (11)0.0257 (12)0.0077 (11)
S50.0469 (5)0.0497 (5)0.0531 (5)0.0028 (3)0.0174 (4)0.0104 (3)
O60.0572 (12)0.0568 (13)0.0547 (12)0.0015 (10)0.0189 (10)0.0130 (10)
C70.0373 (12)0.0625 (17)0.0407 (13)0.0004 (12)0.0215 (11)0.0097 (12)
C80.0515 (16)0.0606 (18)0.0477 (15)0.0036 (13)0.0254 (13)0.0057 (13)
C90.076 (2)0.077 (2)0.0535 (18)0.0149 (18)0.0335 (17)0.0020 (16)
C100.0600 (19)0.098 (3)0.0405 (15)0.0147 (19)0.0159 (14)0.0109 (17)
C110.0561 (19)0.103 (3)0.0525 (19)0.0067 (19)0.0215 (16)0.0243 (19)
C120.0505 (16)0.070 (2)0.0469 (15)0.0063 (15)0.0221 (13)0.0141 (14)
C130.0407 (14)0.0576 (16)0.0397 (13)0.0076 (12)0.0184 (11)0.0043 (12)
C140.0371 (13)0.0546 (16)0.0343 (12)0.0029 (11)0.0152 (10)0.0042 (10)
C150.0490 (15)0.0577 (17)0.0452 (14)0.0023 (13)0.0173 (12)0.0002 (13)
C160.0471 (16)0.090 (3)0.0595 (19)0.0204 (17)0.0227 (15)0.0028 (17)
C170.0496 (17)0.104 (3)0.065 (2)0.0006 (17)0.0360 (16)0.0011 (19)
C180.0634 (19)0.073 (2)0.0630 (18)0.0080 (16)0.0402 (16)0.0040 (16)
C190.0498 (15)0.0540 (16)0.0508 (15)0.0004 (12)0.0272 (13)0.0011 (12)
Geometric parameters (Å, º) top
N1—C21.316 (4)C11—C121.388 (5)
N1—C131.453 (3)C11—H110.93
N1—H10.86C12—H120.93
C2—N31.393 (3)C13—C141.509 (4)
C2—S51.677 (3)C13—H13A0.97
N3—C41.375 (4)C13—H13B0.97
N3—H30.86C14—C191.382 (4)
C4—O61.215 (4)C14—C151.386 (4)
C4—C71.498 (4)C15—C161.393 (5)
C7—C81.377 (5)C15—H150.93
C7—C121.388 (4)C16—C171.362 (6)
C8—C91.386 (5)C16—H160.93
C8—H80.93C17—C181.372 (5)
C9—C101.381 (6)C17—H170.93
C9—H90.93C18—C191.385 (4)
C10—C111.359 (6)C18—H180.93
C10—H100.93C19—H190.93
C2—N1—C13124.9 (2)C7—C12—C11119.3 (4)
C2—N1—H1117.6C7—C12—H12120.3
C13—N1—H1117.6C11—C12—H12120.3
N1—C2—N3117.2 (2)N1—C13—C14112.8 (2)
N1—C2—S5125.3 (2)N1—C13—H13A109
N3—C2—S5117.5 (2)C14—C13—H13A109
C4—N3—C2127.6 (2)N1—C13—H13B109
C4—N3—H3116.2C14—C13—H13B109
C2—N3—H3116.2H13A—C13—H13B107.8
O6—C4—N3123.3 (3)C19—C14—C15119.4 (3)
O6—C4—C7121.7 (3)C19—C14—C13120.3 (3)
N3—C4—C7115.0 (2)C15—C14—C13120.3 (3)
C8—C7—C12119.7 (3)C14—C15—C16119.5 (3)
C8—C7—C4123.2 (3)C14—C15—H15120.2
C12—C7—C4116.9 (3)C16—C15—H15120.2
C7—C8—C9120.4 (3)C17—C16—C15120.3 (3)
C7—C8—H8119.8C17—C16—H16119.9
C9—C8—H8119.8C15—C16—H16119.9
C10—C9—C8119.3 (4)C16—C17—C18120.7 (3)
C10—C9—H9120.3C16—C17—H17119.7
C8—C9—H9120.3C18—C17—H17119.7
C11—C10—C9120.6 (3)C17—C18—C19119.6 (3)
C11—C10—H10119.7C17—C18—H18120.2
C9—C10—H10119.7C19—C18—H18120.2
C10—C11—C12120.5 (4)C14—C19—C18120.5 (3)
C10—C11—H11119.7C14—C19—H19119.8
C12—C11—H11119.7C18—C19—H19119.8
C13—N1—C2—N3176.9 (2)C8—C7—C12—C110.7 (4)
C13—N1—C2—S52.9 (4)C4—C7—C12—C11175.1 (3)
N1—C2—N3—C43.8 (4)C10—C11—C12—C72.0 (5)
S5—C2—N3—C4176.0 (2)C2—N1—C13—C14107.0 (3)
C2—N3—C4—O67.4 (4)N1—C13—C14—C1979.6 (3)
C2—N3—C4—C7170.8 (2)N1—C13—C14—C15102.4 (3)
O6—C4—C7—C8147.2 (3)C19—C14—C15—C160.2 (4)
N3—C4—C7—C831.0 (4)C13—C14—C15—C16178.2 (3)
O6—C4—C7—C1228.4 (4)C14—C15—C16—C170.3 (5)
N3—C4—C7—C12153.3 (2)C15—C16—C17—C180.3 (6)
C12—C7—C8—C93.0 (4)C16—C17—C18—C190.2 (5)
C4—C7—C8—C9172.6 (3)C15—C14—C19—C180.1 (4)
C7—C8—C9—C102.5 (5)C13—C14—C19—C18178.1 (3)
C8—C9—C10—C110.2 (6)C17—C18—C19—C140.1 (5)
C9—C10—C11—C122.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O60.861.982.663 (3)136
N3—H3···S5i0.862.733.479 (2)146
C13—H13A···S50.972.643.121 (3)111
C13—H13B···S5ii0.972.863.610 (3)135
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z.
 

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