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The title compound, C12H20N4O2S, has been synthesized for use as an inter­mediate for antihypertensive agents, potential antimalarials and mol­ecular rectification materials. The inter­molecular S...N non-bonded separation within a column in the crystal structure is 3.308 (2) Å, indicating a strong inter­molecular inter­action between the cyano groups and the S atoms. Attractive C—H...O hydrogen bonds are responsible for zigzag mol­ecular chains propagating in the a-axis direction; these types of inter­molecular inter­actions combine to form an extended three-dimensional network in the lattice.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026280/bd6009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026280/bd6009Isup2.hkl
Contains datablock I

CCDC reference: 283745

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.097
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C5 .. 5.32 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.30
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.01 From the CIF: _reflns_number_total 2875 Count of symmetry unique reflns 1696 Completeness (_total/calc) 169.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1179 Fraction of Friedel pairs measured 0.695 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Methyl 4-tert-butoxycarbonyl-N-cyanopiperazine-1-carboximidothioate top
Crystal data top
C12H20N4O2SDx = 1.285 Mg m3
Mr = 284.38Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2619 reflections
a = 6.358 (2) Åθ = 2.3–22.1°
b = 9.382 (3) ŵ = 0.23 mm1
c = 24.646 (8) ÅT = 273 K
V = 1470.1 (8) Å3Spicula, yellow
Z = 40.20 × 0.15 × 0.10 mm
F(000) = 608
Data collection top
Bruker SMART CCD area-detector
diffractometer
2875 independent reflections
Radiation source: fine-focus sealed tube2436 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.956, Tmax = 0.978k = 1110
7193 measured reflectionsl = 3029
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.11P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2875 reflectionsΔρmax = 0.21 e Å3
173 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.0 (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
xyzUiso*/Ueq
C10.7178 (6)1.0313 (4)0.12784 (10)0.0842 (10)
H1A0.63660.94630.13360.126*
H1B0.85871.00580.11780.126*
H1C0.72071.08650.16060.126*
C20.7366 (6)1.2548 (3)0.07259 (13)0.0842 (10)
H2A0.66761.30750.04430.126*
H2B0.73931.31070.10520.126*
H2C0.87791.23310.06170.126*
C30.3898 (5)1.1485 (4)0.09437 (12)0.0884 (10)
H3A0.31761.06050.10140.133*
H3B0.37851.20950.12550.133*
H3C0.32751.19470.06350.133*
C40.6188 (4)1.1184 (2)0.08287 (8)0.0524 (6)
C50.7804 (4)0.9823 (3)0.00919 (8)0.0440 (5)
C60.5205 (4)0.8779 (3)0.05560 (8)0.0498 (6)
H6A0.48610.77790.05110.060*
H6B0.41990.93360.03500.060*
C70.5062 (4)0.9173 (3)0.11470 (7)0.0467 (6)
H7A0.52181.01960.11870.056*
H7B0.36920.89070.12870.056*
C80.8945 (4)0.8364 (3)0.06705 (9)0.0543 (6)
H8A1.03100.86410.05300.065*
H8B0.88190.73380.06350.065*
C90.8809 (4)0.8761 (3)0.12584 (9)0.0457 (5)
H9A0.98380.82240.14650.055*
H9B0.91110.97680.13030.055*
C100.6246 (3)0.7694 (2)0.19003 (7)0.0356 (4)
C110.7863 (5)0.5420 (3)0.24881 (14)0.0761 (9)
H11A0.89660.50590.27160.114*
H11B0.77780.48560.21640.114*
H11C0.65480.53710.26790.114*
C120.3697 (4)0.6860 (3)0.24741 (9)0.0486 (5)
N10.7311 (3)0.9047 (2)0.03538 (7)0.0525 (5)
N20.6699 (3)0.84499 (18)0.14580 (6)0.0388 (4)
N30.4286 (3)0.7408 (2)0.20055 (7)0.0456 (5)
N40.2989 (4)0.6391 (3)0.28653 (9)0.0707 (7)
O10.6075 (3)1.03331 (18)0.03269 (6)0.0531 (4)
O20.9594 (3)0.9996 (2)0.02443 (7)0.0627 (5)
S10.84118 (9)0.72301 (7)0.23127 (2)0.05208 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.128 (3)0.083 (2)0.0420 (12)0.007 (2)0.0034 (16)0.0009 (13)
C20.110 (3)0.0516 (17)0.091 (2)0.0136 (16)0.0077 (18)0.0149 (14)
C30.080 (2)0.114 (3)0.0715 (18)0.0011 (19)0.0130 (17)0.0448 (19)
C40.0684 (17)0.0500 (14)0.0388 (11)0.0047 (12)0.0002 (11)0.0133 (10)
C50.0505 (14)0.0451 (12)0.0365 (11)0.0025 (11)0.0061 (10)0.0010 (9)
C60.0431 (13)0.0681 (16)0.0381 (11)0.0053 (12)0.0029 (10)0.0109 (10)
C70.0401 (13)0.0607 (14)0.0392 (11)0.0086 (11)0.0018 (9)0.0124 (10)
C80.0441 (14)0.0738 (17)0.0449 (12)0.0148 (12)0.0081 (10)0.0119 (11)
C90.0378 (12)0.0527 (13)0.0466 (11)0.0038 (11)0.0011 (9)0.0105 (10)
C100.0408 (11)0.0345 (10)0.0316 (9)0.0015 (9)0.0014 (8)0.0021 (8)
C110.0656 (17)0.0612 (16)0.101 (2)0.0162 (14)0.0079 (16)0.0339 (16)
C120.0400 (12)0.0608 (14)0.0449 (11)0.0055 (11)0.0011 (10)0.0113 (10)
N10.0446 (11)0.0767 (14)0.0362 (9)0.0058 (10)0.0052 (8)0.0149 (9)
N20.0350 (9)0.0483 (10)0.0331 (8)0.0026 (8)0.0002 (7)0.0065 (7)
N30.0419 (10)0.0573 (12)0.0376 (9)0.0026 (9)0.0010 (7)0.0091 (8)
N40.0582 (13)0.0947 (18)0.0592 (12)0.0091 (12)0.0116 (11)0.0321 (12)
O10.0485 (10)0.0661 (10)0.0449 (8)0.0011 (8)0.0019 (7)0.0216 (7)
O20.0532 (10)0.0767 (12)0.0582 (10)0.0014 (9)0.0129 (9)0.0180 (9)
S10.0477 (3)0.0596 (4)0.0489 (3)0.0031 (3)0.0119 (3)0.0159 (3)
Geometric parameters (Å, º) top
C1—C41.514 (4)C7—N21.460 (3)
C1—H1A0.9600C7—H7A0.9700
C1—H1B0.9600C7—H7B0.9700
C1—H1C0.9600C8—N11.449 (3)
C2—C41.504 (4)C8—C91.499 (3)
C2—H2A0.9600C8—H8A0.9700
C2—H2B0.9600C8—H8B0.9700
C2—H2C0.9600C9—N21.458 (3)
C3—C41.510 (4)C9—H9A0.9700
C3—H3A0.9600C9—H9B0.9700
C3—H3B0.9600C10—N31.301 (3)
C3—H3C0.9600C10—N21.332 (2)
C4—O11.474 (3)C10—S11.766 (2)
C5—O21.209 (3)C11—S11.787 (3)
C5—O11.332 (3)C11—H11A0.9600
C5—N11.355 (3)C11—H11B0.9600
C6—N11.451 (3)C11—H11C0.9600
C6—C71.506 (3)C12—N41.152 (3)
C6—H6A0.9700C12—N31.319 (3)
C6—H6B0.9700
C4—C1—H1A109.5C6—C7—H7A109.5
C4—C1—H1B109.5N2—C7—H7B109.5
H1A—C1—H1B109.5C6—C7—H7B109.5
C4—C1—H1C109.5H7A—C7—H7B108.1
H1A—C1—H1C109.5N1—C8—C9111.7 (2)
H1B—C1—H1C109.5N1—C8—H8A109.3
C4—C2—H2A109.5C9—C8—H8A109.3
C4—C2—H2B109.5N1—C8—H8B109.3
H2A—C2—H2B109.5C9—C8—H8B109.3
C4—C2—H2C109.5H8A—C8—H8B107.9
H2A—C2—H2C109.5N2—C9—C8109.24 (19)
H2B—C2—H2C109.5N2—C9—H9A109.8
C4—C3—H3A109.5C8—C9—H9A109.8
C4—C3—H3B109.5N2—C9—H9B109.8
H3A—C3—H3B109.5C8—C9—H9B109.8
C4—C3—H3C109.5H9A—C9—H9B108.3
H3A—C3—H3C109.5N3—C10—N2118.68 (18)
H3B—C3—H3C109.5N3—C10—S1125.54 (15)
O1—C4—C2110.09 (19)N2—C10—S1115.72 (15)
O1—C4—C3102.24 (19)S1—C11—H11A109.5
C2—C4—C3110.6 (2)S1—C11—H11B109.5
O1—C4—C1110.0 (2)H11A—C11—H11B109.5
C2—C4—C1112.0 (2)S1—C11—H11C109.5
C3—C4—C1111.4 (2)H11A—C11—H11C109.5
O2—C5—O1126.4 (2)H11B—C11—H11C109.5
O2—C5—N1122.8 (2)N4—C12—N3173.5 (3)
O1—C5—N1110.78 (19)C5—N1—C8120.57 (19)
N1—C6—C7110.21 (19)C5—N1—C6125.81 (19)
N1—C6—H6A109.6C8—N1—C6113.61 (17)
C7—C6—H6A109.6C10—N2—C9125.56 (17)
N1—C6—H6B109.6C10—N2—C7121.54 (17)
C7—C6—H6B109.6C9—N2—C7112.68 (16)
H6A—C6—H6B108.1C10—N3—C12121.83 (18)
N2—C7—C6110.54 (19)C5—O1—C4121.29 (18)
N2—C7—H7A109.5C10—S1—C11102.78 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O20.962.392.991 (2)120
C2—H2C···O20.962.433.025 (2)120
C6—H6A···O2i0.972.693.645 (3)168
C9—H9A···S10.972.462.980 (2)113
C11—H11C···N40.962.503.361 (2)149
C11—H11C···C120.962.342.974 (2)123
Symmetry code: (i) x1/2, y+3/2, z.
 

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