The title compound, C
17H
17N
5OS, adopts the configurations
Z around the imine C=N bond and
E around the C(O)—NH bond. The configurations are stabilized by two intramolecular N—H
N hydrogen bonds. In the crystal structure, molecules are linked together by N—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 621448
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.071
- wR factor = 0.211
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 431.00 A 3
| Author Response: SQUEEZE program was employed to remove the disordered solvent in the
solvent accecible voids. The disordered solvent is found to be ethylacetate
which is used for crystallization.
|
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
PLAT414_ALERT_2_B Short Intra D-H..H-X H2 .. H5B .. 1.85 Ang.
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.77 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O12 - C1 .. 5.58 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3B
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.
2-(1
H-1,3-Benzimidazol-2-ylsulfanyl)-1-(4-methylphenyl)ethanone
semicarbazone
top
Crystal data top
C17H17N5OS | Melting point: 445 K |
Mr = 339.43 | Mo Kα radiation, λ = 0.71069 Å |
Tetragonal, I41/a | Cell parameters from 25 reflections |
a = 21.525 (5) Å | θ = 10.0–13.9° |
c = 17.396 (4) Å | µ = 0.17 mm−1 |
V = 8060 (4) Å3 | T = 293 K |
Z = 16 | Block, colourless |
F(000) = 2848 | 0.21 × 0.18 × 0.14 mm |
Dx = 1.119 Mg m−3 Dm = 1.08 (5) Mg m−3 Dm measured by flotation in a mixture of xylene and carbon tetrachloride | |
Data collection top
Nonius MACH3 sealed-tube diffractometer | Rint = 0.057 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.4° |
Graphite monochromator | h = 0→25 |
ω–2θ scans | k = 0→25 |
4008 measured reflections | l = −1→20 |
3534 independent reflections | 3 standard reflections every 60 min |
1189 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.1015P)2] where P = (Fo2 + 2Fc2)/3 |
3534 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N11 | 0.5123 (2) | 0.1589 (2) | 0.2713 (2) | 0.0663 (13) | |
H11A | 0.4849 | 0.1817 | 0.2935 | 0.080* | |
H11B | 0.5070 | 0.1473 | 0.2245 | 0.080* | |
O12 | 0.57371 (16) | 0.15675 (15) | 0.3773 (2) | 0.0549 (10) | |
C1 | 0.5630 (2) | 0.1416 (2) | 0.3095 (3) | 0.0482 (13) | |
N2 | 0.60433 (19) | 0.10397 (18) | 0.2730 (2) | 0.0507 (11) | |
H2 | 0.6376 | 0.0919 | 0.2960 | 0.061* | |
N3 | 0.5922 (2) | 0.0852 (2) | 0.1981 (2) | 0.0562 (12) | |
C4 | 0.6296 (3) | 0.0446 (3) | 0.1693 (3) | 0.0557 (15) | |
C5 | 0.6838 (3) | 0.0148 (3) | 0.2101 (3) | 0.0653 (17) | |
H5A | 0.6825 | −0.0297 | 0.2007 | 0.078* | |
H5B | 0.6789 | 0.0211 | 0.2649 | 0.078* | |
S6 | 0.75954 (7) | 0.04394 (8) | 0.18116 (9) | 0.0725 (5) | |
C7 | 0.7678 (3) | 0.1083 (3) | 0.2423 (3) | 0.0561 (15) | |
N8 | 0.8157 (2) | 0.1480 (2) | 0.2323 (3) | 0.0608 (13) | |
H8 | 0.8442 | 0.1458 | 0.1977 | 0.073* | |
N9 | 0.7319 (2) | 0.1223 (2) | 0.3012 (2) | 0.0576 (12) | |
C1A | 0.8101 (3) | 0.1925 (3) | 0.2886 (3) | 0.0589 (15) | |
C2A | 0.8440 (3) | 0.2445 (3) | 0.3055 (4) | 0.0786 (19) | |
H2A | 0.8789 | 0.2552 | 0.2769 | 0.094* | |
C3A | 0.8246 (3) | 0.2801 (3) | 0.3659 (5) | 0.088 (2) | |
H3A | 0.8468 | 0.3156 | 0.3786 | 0.106* | |
C4A | 0.7724 (3) | 0.2646 (3) | 0.4089 (4) | 0.081 (2) | |
H4A | 0.7605 | 0.2902 | 0.4494 | 0.098* | |
C5A | 0.7381 (3) | 0.2125 (3) | 0.3932 (3) | 0.0674 (17) | |
H5A1 | 0.7036 | 0.2017 | 0.4226 | 0.081* | |
C6A | 0.7573 (2) | 0.1765 (3) | 0.3310 (3) | 0.0537 (14) | |
C1B | 0.6184 (3) | 0.0267 (3) | 0.0879 (3) | 0.0645 (16) | |
C2B | 0.5795 (3) | 0.0612 (4) | 0.0428 (4) | 0.095 (2) | |
H2B | 0.5606 | 0.0967 | 0.0624 | 0.114* | |
C3B | 0.5684 (4) | 0.0430 (5) | −0.0321 (5) | 0.125 (3) | |
H3B | 0.5417 | 0.0669 | −0.0620 | 0.150* | |
C4B | 0.5951 (4) | −0.0091 (5) | −0.0649 (4) | 0.103 (3) | |
C5B | 0.6339 (4) | −0.0415 (4) | −0.0207 (4) | 0.099 (2) | |
H5B1 | 0.6537 | −0.0762 | −0.0410 | 0.119* | |
C6B | 0.6454 (3) | −0.0249 (3) | 0.0550 (4) | 0.0856 (19) | |
H6B | 0.6721 | −0.0492 | 0.0844 | 0.103* | |
C7B | 0.5807 (4) | −0.0277 (5) | −0.1481 (4) | 0.153 (4) | |
H7B1 | 0.6188 | −0.0311 | −0.1765 | 0.230* | |
H7B2 | 0.5548 | 0.0034 | −0.1714 | 0.230* | |
H7B3 | 0.5596 | −0.0669 | −0.1486 | 0.230* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.056 (3) | 0.079 (3) | 0.064 (3) | 0.016 (3) | 0.009 (3) | −0.008 (3) |
O12 | 0.068 (3) | 0.053 (2) | 0.044 (2) | 0.0016 (18) | 0.000 (2) | −0.0047 (18) |
C1 | 0.042 (3) | 0.045 (3) | 0.057 (4) | −0.002 (3) | 0.012 (3) | 0.013 (3) |
N2 | 0.046 (3) | 0.063 (3) | 0.043 (3) | 0.006 (2) | 0.007 (2) | 0.004 (2) |
N3 | 0.058 (3) | 0.071 (3) | 0.039 (3) | −0.009 (3) | 0.007 (2) | 0.000 (2) |
C4 | 0.057 (4) | 0.055 (4) | 0.056 (4) | −0.014 (3) | 0.011 (3) | −0.001 (3) |
C5 | 0.077 (4) | 0.054 (4) | 0.065 (4) | −0.004 (3) | 0.011 (3) | −0.006 (3) |
S6 | 0.0615 (11) | 0.0919 (13) | 0.0640 (10) | 0.0050 (9) | 0.0097 (8) | −0.0077 (9) |
C7 | 0.050 (4) | 0.063 (4) | 0.055 (4) | −0.007 (3) | −0.004 (3) | 0.011 (3) |
N8 | 0.043 (3) | 0.085 (4) | 0.055 (3) | −0.015 (3) | 0.003 (2) | 0.015 (3) |
N9 | 0.058 (3) | 0.060 (3) | 0.055 (3) | −0.007 (3) | 0.006 (3) | 0.003 (3) |
C1A | 0.059 (4) | 0.066 (4) | 0.052 (4) | −0.009 (3) | −0.009 (3) | 0.016 (3) |
C2A | 0.070 (5) | 0.067 (5) | 0.099 (5) | −0.020 (4) | 0.004 (4) | 0.016 (4) |
C3A | 0.082 (5) | 0.049 (4) | 0.134 (7) | −0.011 (4) | −0.021 (5) | 0.005 (5) |
C4A | 0.070 (5) | 0.067 (5) | 0.107 (6) | −0.002 (4) | −0.002 (4) | −0.009 (4) |
C5A | 0.062 (4) | 0.062 (4) | 0.078 (5) | −0.004 (4) | 0.007 (3) | −0.001 (4) |
C6A | 0.054 (4) | 0.050 (4) | 0.058 (3) | −0.012 (3) | 0.001 (3) | 0.011 (3) |
C1B | 0.055 (4) | 0.080 (5) | 0.058 (4) | −0.008 (4) | 0.007 (3) | −0.018 (4) |
C2B | 0.110 (6) | 0.123 (6) | 0.053 (4) | 0.032 (5) | −0.013 (4) | −0.026 (4) |
C3B | 0.133 (7) | 0.172 (9) | 0.070 (5) | 0.024 (7) | −0.031 (5) | −0.020 (6) |
C4B | 0.098 (6) | 0.146 (8) | 0.063 (5) | −0.035 (6) | 0.019 (5) | −0.044 (5) |
C5B | 0.107 (6) | 0.110 (6) | 0.080 (6) | −0.013 (5) | 0.001 (5) | −0.038 (5) |
C6B | 0.087 (5) | 0.098 (5) | 0.071 (5) | 0.000 (4) | −0.004 (4) | −0.022 (4) |
C7B | 0.137 (8) | 0.243 (11) | 0.079 (5) | −0.026 (7) | −0.006 (5) | −0.067 (6) |
Geometric parameters (Å, º) top
N11—C1 | 1.331 (6) | C2A—H2A | 0.9300 |
N11—H11A | 0.8600 | C3A—C4A | 1.390 (8) |
N11—H11B | 0.8600 | C3A—H3A | 0.9300 |
O12—C1 | 1.245 (6) | C4A—C5A | 1.369 (7) |
C1—N2 | 1.360 (6) | C4A—H4A | 0.9300 |
N2—N3 | 1.389 (5) | C5A—C6A | 1.395 (7) |
N2—H2 | 0.8600 | C5A—H5A1 | 0.9300 |
N3—C4 | 1.290 (6) | C1B—C2B | 1.368 (8) |
C4—C1B | 1.488 (7) | C1B—C6B | 1.376 (8) |
C4—C5 | 1.508 (7) | C2B—C3B | 1.382 (9) |
C5—S6 | 1.819 (6) | C2B—H2B | 0.9300 |
C5—H5A | 0.9700 | C3B—C4B | 1.383 (10) |
C5—H5B | 0.9700 | C3B—H3B | 0.9300 |
S6—C7 | 1.756 (6) | C4B—C5B | 1.332 (10) |
C7—N9 | 1.318 (6) | C4B—C7B | 1.534 (9) |
C7—N8 | 1.351 (6) | C5B—C6B | 1.387 (8) |
N8—C1A | 1.376 (7) | C5B—H5B1 | 0.9300 |
N8—H8 | 0.8600 | C6B—H6B | 0.9300 |
N9—C6A | 1.389 (6) | C7B—H7B1 | 0.9600 |
C1A—C2A | 1.367 (8) | C7B—H7B2 | 0.9600 |
C1A—C6A | 1.398 (7) | C7B—H7B3 | 0.9600 |
C2A—C3A | 1.366 (8) | | |
| | | |
C1—N11—H11A | 120.0 | C4A—C3A—H3A | 119.1 |
C1—N11—H11B | 120.0 | C5A—C4A—C3A | 121.6 (6) |
H11A—N11—H11B | 120.0 | C5A—C4A—H4A | 119.2 |
O12—C1—N11 | 123.4 (5) | C3A—C4A—H4A | 119.2 |
O12—C1—N2 | 118.5 (5) | C4A—C5A—C6A | 116.7 (6) |
N11—C1—N2 | 118.0 (5) | C4A—C5A—H5A1 | 121.6 |
C1—N2—N3 | 119.2 (4) | C6A—C5A—H5A1 | 121.6 |
C1—N2—H2 | 120.4 | N9—C6A—C5A | 129.7 (5) |
N3—N2—H2 | 120.4 | N9—C6A—C1A | 109.3 (5) |
C4—N3—N2 | 116.4 (4) | C5A—C6A—C1A | 120.9 (5) |
N3—C4—C1B | 116.4 (5) | C2B—C1B—C6B | 117.3 (6) |
N3—C4—C5 | 126.0 (5) | C2B—C1B—C4 | 120.3 (6) |
C1B—C4—C5 | 117.5 (5) | C6B—C1B—C4 | 122.4 (6) |
C4—C5—S6 | 114.5 (4) | C1B—C2B—C3B | 119.5 (7) |
C4—C5—H5A | 108.6 | C1B—C2B—H2B | 120.3 |
S6—C5—H5A | 108.6 | C3B—C2B—H2B | 120.3 |
C4—C5—H5B | 108.6 | C2B—C3B—C4B | 123.2 (8) |
S6—C5—H5B | 108.6 | C2B—C3B—H3B | 118.4 |
H5A—C5—H5B | 107.6 | C4B—C3B—H3B | 118.4 |
C7—S6—C5 | 101.3 (3) | C5B—C4B—C3B | 116.5 (7) |
N9—C7—N8 | 113.8 (5) | C5B—C4B—C7B | 122.3 (9) |
N9—C7—S6 | 126.3 (4) | C3B—C4B—C7B | 121.1 (9) |
N8—C7—S6 | 119.8 (5) | C4B—C5B—C6B | 121.7 (8) |
C7—N8—C1A | 106.3 (5) | C4B—C5B—H5B1 | 119.2 |
C7—N8—H8 | 126.8 | C6B—C5B—H5B1 | 119.2 |
C1A—N8—H8 | 126.8 | C1B—C6B—C5B | 121.8 (7) |
C7—N9—C6A | 104.5 (5) | C1B—C6B—H6B | 119.1 |
C2A—C1A—N8 | 132.6 (6) | C5B—C6B—H6B | 119.1 |
C2A—C1A—C6A | 121.5 (6) | C4B—C7B—H7B1 | 109.5 |
N8—C1A—C6A | 106.0 (5) | C4B—C7B—H7B2 | 109.5 |
C3A—C2A—C1A | 117.5 (6) | H7B1—C7B—H7B2 | 109.5 |
C3A—C2A—H2A | 121.3 | C4B—C7B—H7B3 | 109.5 |
C1A—C2A—H2A | 121.3 | H7B1—C7B—H7B3 | 109.5 |
C2A—C3A—C4A | 121.8 (6) | H7B2—C7B—H7B3 | 109.5 |
C2A—C3A—H3A | 119.1 | | |
| | | |
O12—C1—N2—N3 | 178.2 (4) | C7—N9—C6A—C1A | −1.6 (6) |
N11—C1—N2—N3 | 0.0 (6) | C4A—C5A—C6A—N9 | −179.4 (5) |
C1—N2—N3—C4 | −173.2 (4) | C4A—C5A—C6A—C1A | 1.6 (8) |
N2—N3—C4—C1B | −177.3 (4) | C2A—C1A—C6A—N9 | 179.6 (5) |
N2—N3—C4—C5 | 1.8 (7) | N8—C1A—C6A—N9 | 0.8 (6) |
N3—C4—C5—S6 | −104.9 (6) | C2A—C1A—C6A—C5A | −1.3 (8) |
C1B—C4—C5—S6 | 74.2 (5) | N8—C1A—C6A—C5A | 180.0 (5) |
C4—C5—S6—C7 | 86.5 (4) | N3—C4—C1B—C2B | 13.5 (8) |
C5—S6—C7—N9 | 10.4 (6) | C5—C4—C1B—C2B | −165.7 (6) |
C5—S6—C7—N8 | −171.8 (4) | N3—C4—C1B—C6B | −165.7 (6) |
N9—C7—N8—C1A | −1.3 (6) | C5—C4—C1B—C6B | 15.1 (8) |
S6—C7—N8—C1A | −179.4 (4) | C6B—C1B—C2B—C3B | 0.8 (10) |
N8—C7—N9—C6A | 1.8 (6) | C4—C1B—C2B—C3B | −178.4 (6) |
S6—C7—N9—C6A | 179.7 (4) | C1B—C2B—C3B—C4B | −0.2 (13) |
C7—N8—C1A—C2A | −178.3 (6) | C2B—C3B—C4B—C5B | −1.2 (13) |
C7—N8—C1A—C6A | 0.2 (6) | C2B—C3B—C4B—C7B | 179.4 (8) |
N8—C1A—C2A—C3A | 178.8 (6) | C3B—C4B—C5B—C6B | 1.9 (12) |
C6A—C1A—C2A—C3A | 0.4 (9) | C7B—C4B—C5B—C6B | −178.7 (7) |
C1A—C2A—C3A—C4A | −0.1 (10) | C2B—C1B—C6B—C5B | −0.1 (10) |
C2A—C3A—C4A—C5A | 0.5 (10) | C4—C1B—C6B—C5B | 179.1 (6) |
C3A—C4A—C5A—C6A | −1.2 (9) | C4B—C5B—C6B—C1B | −1.3 (12) |
C7—N9—C6A—C5A | 179.4 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···O12i | 0.86 | 2.18 | 2.901 (5) | 142 |
N11—H11B···N3 | 0.86 | 2.31 | 2.663 (6) | 105 |
N2—H2···N9 | 0.86 | 2.13 | 2.817 (6) | 136 |
N8—H8···O12ii | 0.86 | 1.93 | 2.747 (6) | 157 |
Symmetry codes: (i) y+1/4, −x+3/4, −z+3/4; (ii) y+3/4, −x+3/4, z−1/4. |