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The title compound, C17H17N5OS, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031485/ob2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031485/ob2042Isup2.hkl
Contains datablock I

CCDC reference: 621448

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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-(1H-1,3-Benzimidazol-2-ylsulfanyl)-1-(4-methylphenyl)ethanone semicarbazone top
Crystal data top
C17H17N5OSMelting point: 445 K
Mr = 339.43Mo Kα radiation, λ = 0.71069 Å
Tetragonal, I41/aCell parameters from 25 reflections
a = 21.525 (5) Åθ = 10.0–13.9°
c = 17.396 (4) ŵ = 0.17 mm1
V = 8060 (4) Å3T = 293 K
Z = 16Block, colourless
F(000) = 28480.21 × 0.18 × 0.14 mm
Dx = 1.119 Mg m3
Dm = 1.08 (5) Mg m3
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 tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 025
ω–2θ scansk = 025
4008 measured reflectionsl = 120
3534 independent reflections3 standard reflections every 60 min
1189 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H-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 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
N110.5123 (2)0.1589 (2)0.2713 (2)0.0663 (13)
H11A0.48490.18170.29350.080*
H11B0.50700.14730.22450.080*
O120.57371 (16)0.15675 (15)0.3773 (2)0.0549 (10)
C10.5630 (2)0.1416 (2)0.3095 (3)0.0482 (13)
N20.60433 (19)0.10397 (18)0.2730 (2)0.0507 (11)
H20.63760.09190.29600.061*
N30.5922 (2)0.0852 (2)0.1981 (2)0.0562 (12)
C40.6296 (3)0.0446 (3)0.1693 (3)0.0557 (15)
C50.6838 (3)0.0148 (3)0.2101 (3)0.0653 (17)
H5A0.68250.02970.20070.078*
H5B0.67890.02110.26490.078*
S60.75954 (7)0.04394 (8)0.18116 (9)0.0725 (5)
C70.7678 (3)0.1083 (3)0.2423 (3)0.0561 (15)
N80.8157 (2)0.1480 (2)0.2323 (3)0.0608 (13)
H80.84420.14580.19770.073*
N90.7319 (2)0.1223 (2)0.3012 (2)0.0576 (12)
C1A0.8101 (3)0.1925 (3)0.2886 (3)0.0589 (15)
C2A0.8440 (3)0.2445 (3)0.3055 (4)0.0786 (19)
H2A0.87890.25520.27690.094*
C3A0.8246 (3)0.2801 (3)0.3659 (5)0.088 (2)
H3A0.84680.31560.37860.106*
C4A0.7724 (3)0.2646 (3)0.4089 (4)0.081 (2)
H4A0.76050.29020.44940.098*
C5A0.7381 (3)0.2125 (3)0.3932 (3)0.0674 (17)
H5A10.70360.20170.42260.081*
C6A0.7573 (2)0.1765 (3)0.3310 (3)0.0537 (14)
C1B0.6184 (3)0.0267 (3)0.0879 (3)0.0645 (16)
C2B0.5795 (3)0.0612 (4)0.0428 (4)0.095 (2)
H2B0.56060.09670.06240.114*
C3B0.5684 (4)0.0430 (5)0.0321 (5)0.125 (3)
H3B0.54170.06690.06200.150*
C4B0.5951 (4)0.0091 (5)0.0649 (4)0.103 (3)
C5B0.6339 (4)0.0415 (4)0.0207 (4)0.099 (2)
H5B10.65370.07620.04100.119*
C6B0.6454 (3)0.0249 (3)0.0550 (4)0.0856 (19)
H6B0.67210.04920.08440.103*
C7B0.5807 (4)0.0277 (5)0.1481 (4)0.153 (4)
H7B10.61880.03110.17650.230*
H7B20.55480.00340.17140.230*
H7B30.55960.06690.14860.230*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.056 (3)0.079 (3)0.064 (3)0.016 (3)0.009 (3)0.008 (3)
O120.068 (3)0.053 (2)0.044 (2)0.0016 (18)0.000 (2)0.0047 (18)
C10.042 (3)0.045 (3)0.057 (4)0.002 (3)0.012 (3)0.013 (3)
N20.046 (3)0.063 (3)0.043 (3)0.006 (2)0.007 (2)0.004 (2)
N30.058 (3)0.071 (3)0.039 (3)0.009 (3)0.007 (2)0.000 (2)
C40.057 (4)0.055 (4)0.056 (4)0.014 (3)0.011 (3)0.001 (3)
C50.077 (4)0.054 (4)0.065 (4)0.004 (3)0.011 (3)0.006 (3)
S60.0615 (11)0.0919 (13)0.0640 (10)0.0050 (9)0.0097 (8)0.0077 (9)
C70.050 (4)0.063 (4)0.055 (4)0.007 (3)0.004 (3)0.011 (3)
N80.043 (3)0.085 (4)0.055 (3)0.015 (3)0.003 (2)0.015 (3)
N90.058 (3)0.060 (3)0.055 (3)0.007 (3)0.006 (3)0.003 (3)
C1A0.059 (4)0.066 (4)0.052 (4)0.009 (3)0.009 (3)0.016 (3)
C2A0.070 (5)0.067 (5)0.099 (5)0.020 (4)0.004 (4)0.016 (4)
C3A0.082 (5)0.049 (4)0.134 (7)0.011 (4)0.021 (5)0.005 (5)
C4A0.070 (5)0.067 (5)0.107 (6)0.002 (4)0.002 (4)0.009 (4)
C5A0.062 (4)0.062 (4)0.078 (5)0.004 (4)0.007 (3)0.001 (4)
C6A0.054 (4)0.050 (4)0.058 (3)0.012 (3)0.001 (3)0.011 (3)
C1B0.055 (4)0.080 (5)0.058 (4)0.008 (4)0.007 (3)0.018 (4)
C2B0.110 (6)0.123 (6)0.053 (4)0.032 (5)0.013 (4)0.026 (4)
C3B0.133 (7)0.172 (9)0.070 (5)0.024 (7)0.031 (5)0.020 (6)
C4B0.098 (6)0.146 (8)0.063 (5)0.035 (6)0.019 (5)0.044 (5)
C5B0.107 (6)0.110 (6)0.080 (6)0.013 (5)0.001 (5)0.038 (5)
C6B0.087 (5)0.098 (5)0.071 (5)0.000 (4)0.004 (4)0.022 (4)
C7B0.137 (8)0.243 (11)0.079 (5)0.026 (7)0.006 (5)0.067 (6)
Geometric parameters (Å, º) top
N11—C11.331 (6)C2A—H2A0.9300
N11—H11A0.8600C3A—C4A1.390 (8)
N11—H11B0.8600C3A—H3A0.9300
O12—C11.245 (6)C4A—C5A1.369 (7)
C1—N21.360 (6)C4A—H4A0.9300
N2—N31.389 (5)C5A—C6A1.395 (7)
N2—H20.8600C5A—H5A10.9300
N3—C41.290 (6)C1B—C2B1.368 (8)
C4—C1B1.488 (7)C1B—C6B1.376 (8)
C4—C51.508 (7)C2B—C3B1.382 (9)
C5—S61.819 (6)C2B—H2B0.9300
C5—H5A0.9700C3B—C4B1.383 (10)
C5—H5B0.9700C3B—H3B0.9300
S6—C71.756 (6)C4B—C5B1.332 (10)
C7—N91.318 (6)C4B—C7B1.534 (9)
C7—N81.351 (6)C5B—C6B1.387 (8)
N8—C1A1.376 (7)C5B—H5B10.9300
N8—H80.8600C6B—H6B0.9300
N9—C6A1.389 (6)C7B—H7B10.9600
C1A—C2A1.367 (8)C7B—H7B20.9600
C1A—C6A1.398 (7)C7B—H7B30.9600
C2A—C3A1.366 (8)
C1—N11—H11A120.0C4A—C3A—H3A119.1
C1—N11—H11B120.0C5A—C4A—C3A121.6 (6)
H11A—N11—H11B120.0C5A—C4A—H4A119.2
O12—C1—N11123.4 (5)C3A—C4A—H4A119.2
O12—C1—N2118.5 (5)C4A—C5A—C6A116.7 (6)
N11—C1—N2118.0 (5)C4A—C5A—H5A1121.6
C1—N2—N3119.2 (4)C6A—C5A—H5A1121.6
C1—N2—H2120.4N9—C6A—C5A129.7 (5)
N3—N2—H2120.4N9—C6A—C1A109.3 (5)
C4—N3—N2116.4 (4)C5A—C6A—C1A120.9 (5)
N3—C4—C1B116.4 (5)C2B—C1B—C6B117.3 (6)
N3—C4—C5126.0 (5)C2B—C1B—C4120.3 (6)
C1B—C4—C5117.5 (5)C6B—C1B—C4122.4 (6)
C4—C5—S6114.5 (4)C1B—C2B—C3B119.5 (7)
C4—C5—H5A108.6C1B—C2B—H2B120.3
S6—C5—H5A108.6C3B—C2B—H2B120.3
C4—C5—H5B108.6C2B—C3B—C4B123.2 (8)
S6—C5—H5B108.6C2B—C3B—H3B118.4
H5A—C5—H5B107.6C4B—C3B—H3B118.4
C7—S6—C5101.3 (3)C5B—C4B—C3B116.5 (7)
N9—C7—N8113.8 (5)C5B—C4B—C7B122.3 (9)
N9—C7—S6126.3 (4)C3B—C4B—C7B121.1 (9)
N8—C7—S6119.8 (5)C4B—C5B—C6B121.7 (8)
C7—N8—C1A106.3 (5)C4B—C5B—H5B1119.2
C7—N8—H8126.8C6B—C5B—H5B1119.2
C1A—N8—H8126.8C1B—C6B—C5B121.8 (7)
C7—N9—C6A104.5 (5)C1B—C6B—H6B119.1
C2A—C1A—N8132.6 (6)C5B—C6B—H6B119.1
C2A—C1A—C6A121.5 (6)C4B—C7B—H7B1109.5
N8—C1A—C6A106.0 (5)C4B—C7B—H7B2109.5
C3A—C2A—C1A117.5 (6)H7B1—C7B—H7B2109.5
C3A—C2A—H2A121.3C4B—C7B—H7B3109.5
C1A—C2A—H2A121.3H7B1—C7B—H7B3109.5
C2A—C3A—C4A121.8 (6)H7B2—C7B—H7B3109.5
C2A—C3A—H3A119.1
O12—C1—N2—N3178.2 (4)C7—N9—C6A—C1A1.6 (6)
N11—C1—N2—N30.0 (6)C4A—C5A—C6A—N9179.4 (5)
C1—N2—N3—C4173.2 (4)C4A—C5A—C6A—C1A1.6 (8)
N2—N3—C4—C1B177.3 (4)C2A—C1A—C6A—N9179.6 (5)
N2—N3—C4—C51.8 (7)N8—C1A—C6A—N90.8 (6)
N3—C4—C5—S6104.9 (6)C2A—C1A—C6A—C5A1.3 (8)
C1B—C4—C5—S674.2 (5)N8—C1A—C6A—C5A180.0 (5)
C4—C5—S6—C786.5 (4)N3—C4—C1B—C2B13.5 (8)
C5—S6—C7—N910.4 (6)C5—C4—C1B—C2B165.7 (6)
C5—S6—C7—N8171.8 (4)N3—C4—C1B—C6B165.7 (6)
N9—C7—N8—C1A1.3 (6)C5—C4—C1B—C6B15.1 (8)
S6—C7—N8—C1A179.4 (4)C6B—C1B—C2B—C3B0.8 (10)
N8—C7—N9—C6A1.8 (6)C4—C1B—C2B—C3B178.4 (6)
S6—C7—N9—C6A179.7 (4)C1B—C2B—C3B—C4B0.2 (13)
C7—N8—C1A—C2A178.3 (6)C2B—C3B—C4B—C5B1.2 (13)
C7—N8—C1A—C6A0.2 (6)C2B—C3B—C4B—C7B179.4 (8)
N8—C1A—C2A—C3A178.8 (6)C3B—C4B—C5B—C6B1.9 (12)
C6A—C1A—C2A—C3A0.4 (9)C7B—C4B—C5B—C6B178.7 (7)
C1A—C2A—C3A—C4A0.1 (10)C2B—C1B—C6B—C5B0.1 (10)
C2A—C3A—C4A—C5A0.5 (10)C4—C1B—C6B—C5B179.1 (6)
C3A—C4A—C5A—C6A1.2 (9)C4B—C5B—C6B—C1B1.3 (12)
C7—N9—C6A—C5A179.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O12i0.862.182.901 (5)142
N11—H11B···N30.862.312.663 (6)105
N2—H2···N90.862.132.817 (6)136
N8—H8···O12ii0.861.932.747 (6)157
Symmetry codes: (i) y+1/4, x+3/4, z+3/4; (ii) y+3/4, x+3/4, z1/4.
 

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