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The crystal structure determination of the title compound, C16H14N2S, confirms the amidine nature of this reaction product. In N,N'-diphenylamidines both phenyl groups are nearly orthogonal with the N-C(-C)=N grouping, whereas in this constrained amidine the benzene groups are substantially less twisted [C-C-N-C torsion angles = -17.2 (7) and 38.1 (6)°]. The result is a slightly cupped molecule with the ring-fused benzene rings appearing like the extended wings of a butterfly. The S-C distances of 1.807 (4) and 1.760 (5) Å are significantly different, with the shorter distance representing the S-C bond to a benzene ring.
Supporting information
CCDC reference: 206769
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.041
- wR factor = 0.099
- Data-to-parameter ratio = 7.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.98
From the CIF: _reflns_number_total 1214
Count of symmetry unique reflns 1213
Completeness (_total/calc) 100.08%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present yes
WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C16H14N2S | F(000) = 560 |
Mr = 266.35 | Dx = 1.364 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
a = 22.775 (4) Å | θ = 10–25° |
b = 5.381 (1) Å | µ = 0.24 mm−1 |
c = 10.587 (2) Å | T = 293 K |
V = 1297.5 (4) Å3 | Irregular, white |
Z = 4 | 0.40 × 0.30 × 0.08 mm |
Data collection top
Enraf–Nonius TurboCAD-4 diffractometer | Rint = 0.019 |
non–profiled ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: ψ scan (North, Phillips & Mathews, 1968) | h = −1→27 |
Tmin = 0.954, Tmax = 0.977 | k = 0→6 |
1274 measured reflections | l = 0→12 |
1214 independent reflections | 3 standard reflections every 120 min |
844 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.16 e Å−3 |
1214 reflections | Δρmin = −0.20 e Å−3 |
172 parameters | |
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 | |
C1 | 0.44282 (18) | 0.5428 (9) | 0.4459 (5) | 0.0481 (12) | |
C2 | 0.4880 (2) | 0.5195 (11) | 0.3583 (6) | 0.0621 (14) | |
H2 | 0.4872 | 0.3901 | 0.3001 | 0.075* | |
C3 | 0.5338 (2) | 0.6865 (11) | 0.3570 (5) | 0.0651 (15) | |
H3 | 0.5632 | 0.6733 | 0.2964 | 0.078* | |
C4 | 0.5358 (2) | 0.8722 (10) | 0.4454 (6) | 0.0663 (15) | |
H4 | 0.5668 | 0.9848 | 0.4446 | 0.08* | |
C5 | 0.49222 (17) | 0.8941 (8) | 0.5358 (6) | 0.0561 (13) | |
H5 | 0.4945 | 1.0178 | 0.597 | 0.067* | |
C6 | 0.44493 (16) | 0.7300 (8) | 0.5349 (5) | 0.0464 (11) | |
C7 | 0.35008 (18) | 0.6674 (8) | 0.6054 (5) | 0.0424 (11) | |
C8 | 0.33665 (18) | 0.5082 (9) | 0.4924 (4) | 0.0466 (12) | |
H8 | 0.3233 | 0.6156 | 0.4234 | 0.056* | |
C9 | 0.39129 (18) | 0.3705 (10) | 0.4496 (6) | 0.0620 (14) | |
H9A | 0.3993 | 0.2346 | 0.5073 | 0.074* | |
H9B | 0.3848 | 0.3009 | 0.3662 | 0.074* | |
C10 | 0.3196 (2) | 0.8677 (12) | 0.7997 (5) | 0.0667 (16) | |
H10A | 0.2856 | 0.8877 | 0.8521 | 0.1* | |
H10B | 0.333 | 1.0277 | 0.7716 | 0.1* | |
H10C | 0.3502 | 0.7881 | 0.8473 | 0.1* | |
C11 | 0.2448 (2) | 0.6820 (8) | 0.6598 (4) | 0.0447 (11) | |
C12 | 0.20197 (19) | 0.8427 (10) | 0.7052 (5) | 0.0514 (12) | |
H12 | 0.213 | 0.9802 | 0.7528 | 0.062* | |
C13 | 0.1426 (2) | 0.8009 (10) | 0.6803 (5) | 0.0601 (14) | |
H13 | 0.1145 | 0.9095 | 0.7118 | 0.072* | |
C14 | 0.1258 (2) | 0.5990 (10) | 0.6092 (6) | 0.0608 (15) | |
H14 | 0.0862 | 0.5683 | 0.5939 | 0.073* | |
C15 | 0.16821 (19) | 0.4428 (10) | 0.5609 (5) | 0.0589 (15) | |
H15 | 0.1571 | 0.3084 | 0.5111 | 0.071* | |
C16 | 0.22696 (17) | 0.4831 (8) | 0.5854 (5) | 0.0483 (12) | |
N1 | 0.40020 (14) | 0.7687 (7) | 0.6254 (4) | 0.0468 (10) | |
N2 | 0.30480 (15) | 0.7159 (7) | 0.6911 (4) | 0.0459 (10) | |
S1 | 0.28038 (5) | 0.2798 (2) | 0.52419 (16) | 0.0649 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.042 (2) | 0.050 (3) | 0.052 (3) | 0.004 (2) | −0.007 (3) | 0.002 (3) |
C2 | 0.047 (3) | 0.074 (3) | 0.066 (3) | 0.007 (3) | 0.002 (3) | −0.005 (4) |
C3 | 0.045 (3) | 0.086 (4) | 0.064 (4) | 0.010 (3) | 0.010 (3) | 0.012 (4) |
C4 | 0.040 (3) | 0.062 (3) | 0.097 (4) | −0.002 (2) | 0.010 (4) | 0.009 (4) |
C5 | 0.038 (2) | 0.056 (3) | 0.075 (3) | −0.004 (2) | −0.001 (3) | −0.006 (3) |
C6 | 0.037 (2) | 0.048 (3) | 0.055 (3) | 0.006 (2) | −0.006 (3) | 0.005 (3) |
C7 | 0.043 (2) | 0.038 (3) | 0.046 (3) | 0.003 (2) | −0.007 (2) | 0.010 (3) |
C8 | 0.046 (2) | 0.044 (3) | 0.050 (3) | −0.007 (2) | −0.006 (2) | 0.005 (2) |
C9 | 0.052 (3) | 0.059 (3) | 0.075 (4) | 0.004 (3) | −0.001 (3) | −0.012 (3) |
C10 | 0.055 (3) | 0.101 (4) | 0.044 (3) | −0.016 (3) | 0.002 (3) | −0.017 (3) |
C11 | 0.041 (2) | 0.049 (3) | 0.044 (3) | −0.012 (2) | −0.002 (2) | 0.016 (2) |
C12 | 0.046 (3) | 0.056 (3) | 0.052 (3) | −0.009 (2) | 0.007 (3) | 0.001 (3) |
C13 | 0.046 (3) | 0.068 (4) | 0.066 (4) | 0.002 (3) | 0.011 (3) | 0.012 (3) |
C14 | 0.041 (3) | 0.063 (3) | 0.078 (4) | −0.010 (3) | −0.004 (3) | 0.009 (4) |
C15 | 0.048 (3) | 0.057 (3) | 0.071 (4) | −0.011 (2) | −0.004 (3) | 0.001 (3) |
C16 | 0.043 (3) | 0.044 (3) | 0.058 (3) | −0.008 (2) | 0.000 (2) | 0.008 (3) |
N1 | 0.0348 (18) | 0.053 (2) | 0.052 (2) | −0.0056 (18) | −0.0017 (19) | 0.000 (2) |
N2 | 0.0397 (19) | 0.059 (3) | 0.039 (2) | −0.0085 (19) | −0.0001 (19) | 0.005 (2) |
S1 | 0.0509 (6) | 0.0467 (7) | 0.0972 (11) | −0.0108 (6) | 0.0043 (9) | −0.0094 (10) |
Geometric parameters (Å, º) top
C1—C6 | 1.381 (6) | C9—H9A | 0.97 |
C1—C2 | 1.391 (7) | C9—H9B | 0.97 |
C1—C9 | 1.496 (6) | C10—N2 | 1.450 (6) |
C2—C3 | 1.377 (7) | C10—H10A | 0.96 |
C2—H2 | 0.93 | C10—H10B | 0.96 |
C3—C4 | 1.370 (8) | C10—H10C | 0.96 |
C3—H3 | 0.93 | C11—C16 | 1.390 (6) |
C4—C5 | 1.384 (7) | C11—C12 | 1.390 (7) |
C4—H4 | 0.93 | C11—N2 | 1.417 (6) |
C5—C6 | 1.393 (5) | C12—C13 | 1.395 (6) |
C5—H5 | 0.93 | C12—H12 | 0.93 |
C6—N1 | 1.414 (5) | C13—C14 | 1.376 (7) |
C7—N1 | 1.283 (5) | C13—H13 | 0.93 |
C7—N2 | 1.399 (6) | C14—C15 | 1.379 (7) |
C7—C8 | 1.503 (6) | C14—H14 | 0.93 |
C8—C9 | 1.517 (6) | C15—C16 | 1.380 (5) |
C8—S1 | 1.807 (4) | C15—H15 | 0.93 |
C8—H8 | 0.98 | C16—S1 | 1.760 (5) |
| | | |
C6—C1—C2 | 119.7 (4) | C8—C9—H9B | 109.6 |
C6—C1—C9 | 117.5 (4) | H9A—C9—H9B | 108.1 |
C2—C1—C9 | 122.8 (5) | N2—C10—H10A | 109.5 |
C3—C2—C1 | 120.6 (5) | N2—C10—H10B | 109.5 |
C3—C2—H2 | 119.7 | H10A—C10—H10B | 109.5 |
C1—C2—H2 | 119.7 | N2—C10—H10C | 109.5 |
C4—C3—C2 | 119.6 (5) | H10A—C10—H10C | 109.5 |
C4—C3—H3 | 120.2 | H10B—C10—H10C | 109.5 |
C2—C3—H3 | 120.2 | C16—C11—C12 | 118.0 (4) |
C3—C4—C5 | 120.7 (5) | C16—C11—N2 | 120.9 (4) |
C3—C4—H4 | 119.6 | C12—C11—N2 | 121.1 (4) |
C5—C4—H4 | 119.6 | C11—C12—C13 | 121.0 (5) |
C4—C5—C6 | 119.7 (5) | C11—C12—H12 | 119.5 |
C4—C5—H5 | 120.1 | C13—C12—H12 | 119.5 |
C6—C5—H5 | 120.1 | C14—C13—C12 | 120.0 (5) |
C1—C6—C5 | 119.6 (5) | C14—C13—H13 | 120 |
C1—C6—N1 | 123.0 (4) | C12—C13—H13 | 120 |
C5—C6—N1 | 117.3 (5) | C13—C14—C15 | 119.3 (5) |
N1—C7—N2 | 118.0 (4) | C13—C14—H14 | 120.4 |
N1—C7—C8 | 123.7 (4) | C15—C14—H14 | 120.4 |
N2—C7—C8 | 118.2 (4) | C14—C15—C16 | 120.9 (5) |
C7—C8—C9 | 110.4 (4) | C14—C15—H15 | 119.6 |
C7—C8—S1 | 112.6 (3) | C16—C15—H15 | 119.6 |
C9—C8—S1 | 107.8 (3) | C15—C16—C11 | 120.8 (4) |
C7—C8—H8 | 108.7 | C15—C16—S1 | 120.2 (4) |
C9—C8—H8 | 108.7 | C11—C16—S1 | 119.0 (3) |
S1—C8—H8 | 108.7 | C7—N1—C6 | 117.8 (4) |
C1—C9—C8 | 110.4 (4) | C7—N2—C11 | 122.3 (4) |
C1—C9—H9A | 109.6 | C7—N2—C10 | 116.6 (3) |
C8—C9—H9A | 109.6 | C11—N2—C10 | 118.8 (4) |
C1—C9—H9B | 109.6 | C16—S1—C8 | 97.8 (2) |
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