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In the title compound C
15H
14N
2OS, 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
CCDC reference: 621555
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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
C15H14N2OS | F(000) = 1136 |
Mr = 270.35 | Dx = 1.342 Mg m−3 |
Monoclinic, C2/c | Melting point = 397–398 K |
Hall symbol: -C 2yc | Cu Kα radiation, λ = 1.54180 Å |
a = 30.560 (7) Å | Cell parameters from 25 reflections |
b = 6.112 (2) Å | θ = 14.8–46.6° |
c = 17.364 (4) Å | µ = 2.09 mm−1 |
β = 124.40 (2)° | T = 297 K |
V = 2676.1 (14) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.25 × 0.15 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2125 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 67.9°, θmin = 3.5° |
non–profiled ω/2θ scans | h = −36→30 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.518, Tmax = 0.730 | l = 0→20 |
2569 measured reflections | 2 standard reflections every 120 min |
2439 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | H-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) = 0.199 | Δρmax = 0.59 e Å−3 |
S = 1.15 | Δρmin = −0.38 e Å−3 |
2439 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
173 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.08960 (9) | 0.9770 (4) | 0.05564 (16) | 0.0494 (6) | |
H1 | 0.0752 | 1.0836 | 0.0167 | 0.059* | |
C2 | 0.06464 (10) | 0.7880 (5) | 0.03078 (17) | 0.0420 (6) | |
N3 | 0.01820 (8) | 0.7737 (4) | −0.05851 (15) | 0.0477 (6) | |
H3 | 0.0012 | 0.6519 | −0.0725 | 0.057* | |
C4 | −0.00367 (11) | 0.9316 (5) | −0.12683 (19) | 0.0473 (7) | |
S5 | 0.08431 (3) | 0.56316 (12) | 0.09774 (5) | 0.0559 (3) | |
O6 | 0.01307 (9) | 1.1177 (4) | −0.11381 (15) | 0.0632 (6) | |
C7 | −0.04922 (10) | 0.8561 (5) | −0.22074 (18) | 0.0472 (7) | |
C8 | −0.05384 (12) | 0.6455 (6) | −0.2528 (2) | 0.0548 (7) | |
H8 | −0.0301 | 0.5386 | −0.2129 | 0.066* | |
C9 | −0.09361 (15) | 0.5921 (7) | −0.3441 (2) | 0.0706 (10) | |
H9 | −0.0959 | 0.4513 | −0.3664 | 0.085* | |
C10 | −0.12985 (14) | 0.7500 (7) | −0.4017 (2) | 0.0729 (10) | |
H10 | −0.1566 | 0.7153 | −0.4631 | 0.088* | |
C11 | −0.12686 (15) | 0.9558 (8) | −0.3694 (2) | 0.0757 (11) | |
H11 | −0.1523 | 1.059 | −0.4082 | 0.091* | |
C12 | −0.08610 (12) | 1.0132 (6) | −0.2791 (2) | 0.0588 (8) | |
H12 | −0.0835 | 1.1554 | −0.2578 | 0.071* | |
C13 | 0.13974 (10) | 1.0191 (5) | 0.14400 (18) | 0.0484 (7) | |
H13A | 0.1471 | 0.9004 | 0.1868 | 0.058* | |
H13B | 0.1367 | 1.1528 | 0.1708 | 0.058* | |
C14 | 0.18548 (10) | 1.0409 (5) | 0.13401 (17) | 0.0447 (6) | |
C15 | 0.22077 (11) | 0.8693 (6) | 0.1590 (2) | 0.0558 (7) | |
H15 | 0.2159 | 0.7383 | 0.1805 | 0.067* | |
C16 | 0.26362 (13) | 0.8943 (7) | 0.1518 (2) | 0.0696 (10) | |
H16 | 0.2873 | 0.7794 | 0.1682 | 0.083* | |
C17 | 0.27098 (13) | 1.0864 (7) | 0.1208 (2) | 0.0708 (10) | |
H17 | 0.2998 | 1.1018 | 0.1164 | 0.085* | |
C18 | 0.23634 (13) | 1.2574 (6) | 0.0959 (2) | 0.0638 (9) | |
H18 | 0.2416 | 1.3878 | 0.0746 | 0.077* | |
C19 | 0.19353 (12) | 1.2345 (5) | 0.1026 (2) | 0.0522 (7) | |
H19 | 0.17 | 1.3502 | 0.0858 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0390 (12) | 0.0522 (13) | 0.0465 (12) | −0.0025 (10) | 0.0178 (10) | 0.0057 (10) |
C2 | 0.0341 (12) | 0.0497 (14) | 0.0413 (13) | 0.0016 (10) | 0.0206 (10) | 0.0020 (11) |
N3 | 0.0370 (11) | 0.0540 (13) | 0.0419 (11) | −0.0061 (9) | 0.0161 (10) | 0.0054 (10) |
C4 | 0.0411 (14) | 0.0550 (17) | 0.0471 (14) | 0.0027 (11) | 0.0257 (12) | 0.0077 (11) |
S5 | 0.0469 (5) | 0.0497 (5) | 0.0531 (5) | 0.0028 (3) | 0.0174 (4) | 0.0104 (3) |
O6 | 0.0572 (12) | 0.0568 (13) | 0.0547 (12) | −0.0015 (10) | 0.0189 (10) | 0.0130 (10) |
C7 | 0.0373 (12) | 0.0625 (17) | 0.0407 (13) | 0.0004 (12) | 0.0215 (11) | 0.0097 (12) |
C8 | 0.0515 (16) | 0.0606 (18) | 0.0477 (15) | −0.0036 (13) | 0.0254 (13) | 0.0057 (13) |
C9 | 0.076 (2) | 0.077 (2) | 0.0535 (18) | −0.0149 (18) | 0.0335 (17) | 0.0020 (16) |
C10 | 0.0600 (19) | 0.098 (3) | 0.0405 (15) | −0.0147 (19) | 0.0159 (14) | 0.0109 (17) |
C11 | 0.0561 (19) | 0.103 (3) | 0.0525 (19) | 0.0067 (19) | 0.0215 (16) | 0.0243 (19) |
C12 | 0.0505 (16) | 0.070 (2) | 0.0469 (15) | 0.0063 (15) | 0.0221 (13) | 0.0141 (14) |
C13 | 0.0407 (14) | 0.0576 (16) | 0.0397 (13) | −0.0076 (12) | 0.0184 (11) | −0.0043 (12) |
C14 | 0.0371 (13) | 0.0546 (16) | 0.0343 (12) | −0.0029 (11) | 0.0152 (10) | −0.0042 (10) |
C15 | 0.0490 (15) | 0.0577 (17) | 0.0452 (14) | 0.0023 (13) | 0.0173 (12) | 0.0002 (13) |
C16 | 0.0471 (16) | 0.090 (3) | 0.0595 (19) | 0.0204 (17) | 0.0227 (15) | 0.0028 (17) |
C17 | 0.0496 (17) | 0.104 (3) | 0.065 (2) | −0.0006 (17) | 0.0360 (16) | −0.0011 (19) |
C18 | 0.0634 (19) | 0.073 (2) | 0.0630 (18) | −0.0080 (16) | 0.0402 (16) | 0.0040 (16) |
C19 | 0.0498 (15) | 0.0540 (16) | 0.0508 (15) | 0.0004 (12) | 0.0272 (13) | 0.0011 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.316 (4) | C11—C12 | 1.388 (5) |
N1—C13 | 1.453 (3) | C11—H11 | 0.93 |
N1—H1 | 0.86 | C12—H12 | 0.93 |
C2—N3 | 1.393 (3) | C13—C14 | 1.509 (4) |
C2—S5 | 1.677 (3) | C13—H13A | 0.97 |
N3—C4 | 1.375 (4) | C13—H13B | 0.97 |
N3—H3 | 0.86 | C14—C19 | 1.382 (4) |
C4—O6 | 1.215 (4) | C14—C15 | 1.386 (4) |
C4—C7 | 1.498 (4) | C15—C16 | 1.393 (5) |
C7—C8 | 1.377 (5) | C15—H15 | 0.93 |
C7—C12 | 1.388 (4) | C16—C17 | 1.362 (6) |
C8—C9 | 1.386 (5) | C16—H16 | 0.93 |
C8—H8 | 0.93 | C17—C18 | 1.372 (5) |
C9—C10 | 1.381 (6) | C17—H17 | 0.93 |
C9—H9 | 0.93 | C18—C19 | 1.385 (4) |
C10—C11 | 1.359 (6) | C18—H18 | 0.93 |
C10—H10 | 0.93 | C19—H19 | 0.93 |
| | | |
C2—N1—C13 | 124.9 (2) | C7—C12—C11 | 119.3 (4) |
C2—N1—H1 | 117.6 | C7—C12—H12 | 120.3 |
C13—N1—H1 | 117.6 | C11—C12—H12 | 120.3 |
N1—C2—N3 | 117.2 (2) | N1—C13—C14 | 112.8 (2) |
N1—C2—S5 | 125.3 (2) | N1—C13—H13A | 109 |
N3—C2—S5 | 117.5 (2) | C14—C13—H13A | 109 |
C4—N3—C2 | 127.6 (2) | N1—C13—H13B | 109 |
C4—N3—H3 | 116.2 | C14—C13—H13B | 109 |
C2—N3—H3 | 116.2 | H13A—C13—H13B | 107.8 |
O6—C4—N3 | 123.3 (3) | C19—C14—C15 | 119.4 (3) |
O6—C4—C7 | 121.7 (3) | C19—C14—C13 | 120.3 (3) |
N3—C4—C7 | 115.0 (2) | C15—C14—C13 | 120.3 (3) |
C8—C7—C12 | 119.7 (3) | C14—C15—C16 | 119.5 (3) |
C8—C7—C4 | 123.2 (3) | C14—C15—H15 | 120.2 |
C12—C7—C4 | 116.9 (3) | C16—C15—H15 | 120.2 |
C7—C8—C9 | 120.4 (3) | C17—C16—C15 | 120.3 (3) |
C7—C8—H8 | 119.8 | C17—C16—H16 | 119.9 |
C9—C8—H8 | 119.8 | C15—C16—H16 | 119.9 |
C10—C9—C8 | 119.3 (4) | C16—C17—C18 | 120.7 (3) |
C10—C9—H9 | 120.3 | C16—C17—H17 | 119.7 |
C8—C9—H9 | 120.3 | C18—C17—H17 | 119.7 |
C11—C10—C9 | 120.6 (3) | C17—C18—C19 | 119.6 (3) |
C11—C10—H10 | 119.7 | C17—C18—H18 | 120.2 |
C9—C10—H10 | 119.7 | C19—C18—H18 | 120.2 |
C10—C11—C12 | 120.5 (4) | C14—C19—C18 | 120.5 (3) |
C10—C11—H11 | 119.7 | C14—C19—H19 | 119.8 |
C12—C11—H11 | 119.7 | C18—C19—H19 | 119.8 |
| | | |
C13—N1—C2—N3 | −176.9 (2) | C8—C7—C12—C11 | −0.7 (4) |
C13—N1—C2—S5 | 2.9 (4) | C4—C7—C12—C11 | 175.1 (3) |
N1—C2—N3—C4 | 3.8 (4) | C10—C11—C12—C7 | −2.0 (5) |
S5—C2—N3—C4 | −176.0 (2) | C2—N1—C13—C14 | 107.0 (3) |
C2—N3—C4—O6 | −7.4 (4) | N1—C13—C14—C19 | 79.6 (3) |
C2—N3—C4—C7 | 170.8 (2) | N1—C13—C14—C15 | −102.4 (3) |
O6—C4—C7—C8 | 147.2 (3) | C19—C14—C15—C16 | −0.2 (4) |
N3—C4—C7—C8 | −31.0 (4) | C13—C14—C15—C16 | −178.2 (3) |
O6—C4—C7—C12 | −28.4 (4) | C14—C15—C16—C17 | 0.3 (5) |
N3—C4—C7—C12 | 153.3 (2) | C15—C16—C17—C18 | −0.3 (6) |
C12—C7—C8—C9 | 3.0 (4) | C16—C17—C18—C19 | 0.2 (5) |
C4—C7—C8—C9 | −172.6 (3) | C15—C14—C19—C18 | 0.1 (4) |
C7—C8—C9—C10 | −2.5 (5) | C13—C14—C19—C18 | 178.1 (3) |
C8—C9—C10—C11 | −0.2 (6) | C17—C18—C19—C14 | −0.1 (5) |
C9—C10—C11—C12 | 2.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.86 | 1.98 | 2.663 (3) | 136 |
N3—H3···S5i | 0.86 | 2.73 | 3.479 (2) | 146 |
C13—H13A···S5 | 0.97 | 2.64 | 3.121 (3) | 111 |
C13—H13B···S5ii | 0.97 | 2.86 | 3.610 (3) | 135 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z. |
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