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The title compound, C22H22N6S, has been synthesized as a potent fungicidal agent and its crystal structure investigated. The dihedral angles between the plane of the thia­zole ring and those of the triazole, phenyl and substituted phenyl rings are 53.0 (2), 37.5 (3) and 14.6 (2)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032733/fl6189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032733/fl6189Isup2.hkl
Contains datablock I

CCDC reference: 289721

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.115
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C21 .. 5.02 su PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-[4-(N,N-Diethylamino)benzylidene]-4-phenyl- 5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine top
Crystal data top
C22H22N6SF(000) = 848
Mr = 402.53Dx = 1.290 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2309 reflections
a = 9.0753 (16) Åθ = 2.4–23.4°
b = 20.924 (4) ŵ = 0.18 mm1
c = 11.518 (2) ÅT = 294 K
β = 108.639 (3)°Parallelepiped, yellow
V = 2072.5 (6) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4220 independent reflections
Radiation source: fine-focus sealed tube2444 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.969, Tmax = 0.969k = 2621
11567 measured reflectionsl = 148
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.005P]
where P = (Fo2 + 2Fc2)/3
4220 reflections(Δ/σ)max = 0.002
264 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.27 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
S11.22593 (7)0.52571 (3)0.37432 (6)0.04474 (19)
N11.6744 (2)0.64075 (9)0.62172 (18)0.0493 (5)
N21.5218 (2)0.62076 (9)0.42688 (17)0.0513 (5)
N31.44232 (19)0.61005 (8)0.50788 (16)0.0360 (4)
N41.02160 (19)0.58918 (8)0.43908 (15)0.0374 (4)
N50.9229 (2)0.50005 (8)0.30120 (16)0.0407 (5)
N60.2622 (2)0.37938 (9)0.01706 (18)0.0500 (5)
C11.6579 (3)0.63887 (11)0.5006 (2)0.0540 (7)
H11.73890.64980.47130.065*
C21.5361 (3)0.62248 (10)0.6217 (2)0.0442 (6)
H21.50680.61860.69180.053*
C31.2838 (2)0.59183 (9)0.46619 (18)0.0345 (5)
C41.1622 (2)0.61976 (9)0.49188 (18)0.0323 (5)
C51.1671 (2)0.67602 (10)0.57068 (19)0.0349 (5)
C61.2640 (3)0.72789 (10)0.5728 (2)0.0481 (6)
H61.32550.72840.52180.058*
C71.2687 (3)0.77890 (11)0.6511 (2)0.0597 (7)
H71.33350.81350.65220.072*
C81.1785 (3)0.77882 (12)0.7271 (2)0.0606 (7)
H81.18400.81270.78070.073*
C91.0800 (3)0.72821 (12)0.7233 (2)0.0539 (7)
H91.01720.72850.77310.065*
C101.0738 (2)0.67704 (11)0.6460 (2)0.0427 (6)
H101.00700.64310.64430.051*
C111.0373 (2)0.54014 (10)0.3742 (2)0.0374 (5)
C120.7804 (3)0.51565 (10)0.28455 (19)0.0406 (6)
H120.76070.55180.32410.049*
C130.6503 (2)0.47998 (10)0.20789 (19)0.0359 (5)
C140.6668 (2)0.42262 (10)0.15074 (18)0.0379 (5)
H140.76610.40650.16280.046*
C150.5412 (2)0.38969 (10)0.07773 (19)0.0416 (6)
H150.55690.35150.04220.050*
C160.3879 (2)0.41237 (10)0.05510 (19)0.0385 (5)
C170.3716 (3)0.47059 (10)0.1105 (2)0.0437 (6)
H170.27290.48770.09670.052*
C180.4989 (3)0.50266 (10)0.1845 (2)0.0430 (6)
H180.48370.54090.22040.052*
C190.2752 (3)0.31447 (11)0.0607 (2)0.0588 (7)
H19A0.18390.29020.06140.071*
H19B0.36520.29380.00390.071*
C200.2906 (3)0.31307 (12)0.1869 (3)0.0691 (8)
H20A0.19870.33080.24460.104*
H20B0.30350.26970.20910.104*
H20C0.37950.33780.18740.104*
C210.1041 (3)0.40504 (13)0.0479 (2)0.0576 (7)
H21A0.04110.38750.12590.069*
H21B0.10750.45110.05700.069*
C220.0288 (3)0.38965 (15)0.0483 (3)0.0889 (10)
H22A0.02310.34410.05650.133*
H22B0.07420.40730.02430.133*
H22C0.08950.40770.12540.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0379 (3)0.0450 (4)0.0514 (4)0.0034 (3)0.0144 (3)0.0115 (3)
N10.0376 (12)0.0544 (13)0.0535 (14)0.0051 (9)0.0113 (10)0.0021 (10)
N20.0413 (12)0.0736 (14)0.0454 (12)0.0119 (10)0.0228 (10)0.0123 (11)
N30.0323 (10)0.0402 (11)0.0373 (11)0.0025 (8)0.0136 (9)0.0016 (9)
N40.0320 (10)0.0418 (11)0.0376 (11)0.0026 (8)0.0101 (9)0.0023 (9)
N50.0363 (11)0.0425 (11)0.0406 (11)0.0100 (9)0.0087 (9)0.0065 (9)
N60.0372 (11)0.0520 (12)0.0548 (13)0.0086 (9)0.0062 (10)0.0113 (10)
C10.0400 (15)0.0683 (17)0.0608 (17)0.0142 (12)0.0262 (13)0.0091 (14)
C20.0395 (14)0.0551 (15)0.0361 (14)0.0014 (11)0.0093 (11)0.0022 (11)
C30.0297 (12)0.0381 (12)0.0365 (12)0.0036 (10)0.0118 (10)0.0008 (10)
C40.0309 (12)0.0350 (12)0.0294 (12)0.0030 (9)0.0075 (10)0.0015 (10)
C50.0293 (12)0.0393 (13)0.0328 (12)0.0020 (10)0.0053 (10)0.0010 (10)
C60.0459 (15)0.0445 (14)0.0544 (15)0.0034 (11)0.0167 (12)0.0060 (12)
C70.0583 (17)0.0444 (15)0.0713 (19)0.0075 (13)0.0134 (15)0.0161 (14)
C80.0678 (19)0.0538 (17)0.0490 (16)0.0144 (14)0.0031 (15)0.0170 (13)
C90.0578 (17)0.0639 (17)0.0420 (15)0.0220 (14)0.0188 (13)0.0008 (14)
C100.0355 (13)0.0479 (14)0.0436 (14)0.0062 (11)0.0111 (11)0.0006 (12)
C110.0357 (13)0.0406 (13)0.0363 (13)0.0032 (10)0.0120 (10)0.0013 (11)
C120.0435 (14)0.0402 (13)0.0379 (13)0.0100 (11)0.0128 (11)0.0029 (11)
C130.0341 (12)0.0396 (13)0.0337 (12)0.0067 (10)0.0103 (10)0.0012 (10)
C140.0365 (13)0.0424 (13)0.0342 (12)0.0005 (10)0.0104 (10)0.0026 (11)
C150.0432 (14)0.0406 (13)0.0394 (13)0.0021 (11)0.0109 (11)0.0074 (11)
C160.0353 (13)0.0445 (14)0.0342 (13)0.0060 (11)0.0091 (10)0.0021 (11)
C170.0342 (13)0.0462 (14)0.0493 (15)0.0008 (11)0.0114 (11)0.0023 (12)
C180.0427 (15)0.0404 (13)0.0470 (14)0.0037 (11)0.0158 (12)0.0060 (11)
C190.0529 (16)0.0512 (16)0.0616 (18)0.0138 (12)0.0034 (14)0.0041 (14)
C200.075 (2)0.0584 (17)0.074 (2)0.0054 (14)0.0237 (16)0.0144 (15)
C210.0416 (15)0.0752 (18)0.0520 (16)0.0130 (13)0.0094 (12)0.0051 (14)
C220.067 (2)0.124 (3)0.084 (2)0.0190 (19)0.0360 (18)0.000 (2)
Geometric parameters (Å, º) top
S1—C31.719 (2)C9—C101.382 (3)
S1—C111.738 (2)C9—H90.9300
N1—C21.312 (3)C10—H100.9300
N1—C11.355 (3)C12—C131.437 (3)
N2—C11.311 (3)C12—H120.9300
N2—N31.368 (2)C13—C181.397 (3)
N3—C21.341 (3)C13—C141.400 (3)
N3—C31.415 (2)C14—C151.367 (3)
N4—C111.304 (3)C14—H140.9300
N4—C41.382 (2)C15—C161.413 (3)
N5—C121.287 (3)C15—H150.9300
N5—C111.389 (3)C16—C171.405 (3)
N6—C161.365 (3)C17—C181.372 (3)
N6—C211.465 (3)C17—H170.9300
N6—C191.466 (3)C18—H180.9300
C1—H10.9300C19—C201.504 (3)
C2—H20.9300C19—H19A0.9700
C3—C41.363 (3)C19—H19B0.9700
C4—C51.478 (3)C20—H20A0.9600
C5—C61.392 (3)C20—H20B0.9600
C5—C101.393 (3)C20—H20C0.9600
C6—C71.390 (3)C21—C221.512 (3)
C6—H60.9300C21—H21A0.9700
C7—C81.376 (3)C21—H21B0.9700
C7—H70.9300C22—H22A0.9600
C8—C91.377 (3)C22—H22B0.9600
C8—H80.9300C22—H22C0.9600
C3—S1—C1188.17 (10)N5—C12—H12118.4
C2—N1—C1101.58 (19)C13—C12—H12118.4
C1—N2—N3101.45 (18)C18—C13—C14116.58 (19)
C2—N3—N2109.08 (17)C18—C13—C12120.4 (2)
C2—N3—C3129.98 (18)C14—C13—C12123.0 (2)
N2—N3—C3120.87 (17)C15—C14—C13121.9 (2)
C11—N4—C4111.22 (18)C15—C14—H14119.1
C12—N5—C11117.26 (18)C13—C14—H14119.1
C16—N6—C21121.72 (19)C14—C15—C16121.5 (2)
C16—N6—C19122.3 (2)C14—C15—H15119.2
C21—N6—C19115.88 (19)C16—C15—H15119.2
N2—C1—N1116.5 (2)N6—C16—C17121.7 (2)
N2—C1—H1121.7N6—C16—C15121.6 (2)
N1—C1—H1121.7C17—C16—C15116.62 (19)
N1—C2—N3111.4 (2)C18—C17—C16121.1 (2)
N1—C2—H2124.3C18—C17—H17119.4
N3—C2—H2124.3C16—C17—H17119.4
C4—C3—N3128.09 (19)C17—C18—C13122.3 (2)
C4—C3—S1111.68 (15)C17—C18—H18118.8
N3—C3—S1120.21 (15)C13—C18—H18118.8
C3—C4—N4113.82 (18)N6—C19—C20113.1 (2)
C3—C4—C5127.39 (18)N6—C19—H19A109.0
N4—C4—C5118.77 (18)C20—C19—H19A109.0
C6—C5—C10118.9 (2)N6—C19—H19B109.0
C6—C5—C4121.76 (19)C20—C19—H19B109.0
C10—C5—C4119.31 (18)H19A—C19—H19B107.8
C7—C6—C5119.9 (2)C19—C20—H20A109.5
C7—C6—H6120.1C19—C20—H20B109.5
C5—C6—H6120.1H20A—C20—H20B109.5
C8—C7—C6120.7 (2)C19—C20—H20C109.5
C8—C7—H7119.6H20A—C20—H20C109.5
C6—C7—H7119.6H20B—C20—H20C109.5
C7—C8—C9119.5 (2)N6—C21—C22112.4 (2)
C7—C8—H8120.3N6—C21—H21A109.1
C9—C8—H8120.3C22—C21—H21A109.1
C8—C9—C10120.6 (2)N6—C21—H21B109.1
C8—C9—H9119.7C22—C21—H21B109.1
C10—C9—H9119.7H21A—C21—H21B107.9
C9—C10—C5120.4 (2)C21—C22—H22A109.5
C9—C10—H10119.8C21—C22—H22B109.5
C5—C10—H10119.8H22A—C22—H22B109.5
N4—C11—N5128.6 (2)C21—C22—H22C109.5
N4—C11—S1115.10 (16)H22A—C22—H22C109.5
N5—C11—S1116.20 (16)H22B—C22—H22C109.5
N5—C12—C13123.3 (2)
C1—N2—N3—C20.0 (2)C6—C5—C10—C91.3 (3)
C1—N2—N3—C3177.26 (19)C4—C5—C10—C9177.97 (19)
N3—N2—C1—N10.2 (3)C4—N4—C11—N5175.45 (19)
C2—N1—C1—N20.3 (3)C4—N4—C11—S11.4 (2)
C1—N1—C2—N30.3 (2)C12—N5—C11—N47.3 (3)
N2—N3—C2—N10.2 (2)C12—N5—C11—S1169.54 (16)
C3—N3—C2—N1177.12 (19)C3—S1—C11—N41.19 (17)
C2—N3—C3—C450.1 (3)C3—S1—C11—N5176.05 (16)
N2—N3—C3—C4126.5 (2)C11—N5—C12—C13177.70 (18)
C2—N3—C3—S1128.1 (2)N5—C12—C13—C18174.0 (2)
N2—N3—C3—S155.3 (2)N5—C12—C13—C144.3 (3)
C11—S1—C3—C40.65 (16)C18—C13—C14—C151.3 (3)
C11—S1—C3—N3179.10 (17)C12—C13—C14—C15179.70 (19)
N3—C3—C4—N4178.34 (18)C13—C14—C15—C160.8 (3)
S1—C3—C4—N40.0 (2)C21—N6—C16—C174.4 (3)
N3—C3—C4—C50.4 (3)C19—N6—C16—C17170.9 (2)
S1—C3—C4—C5177.93 (16)C21—N6—C16—C15175.5 (2)
C11—N4—C4—C30.8 (2)C19—N6—C16—C159.2 (3)
C11—N4—C4—C5179.01 (18)C14—C15—C16—N6179.54 (19)
C3—C4—C5—C638.0 (3)C14—C15—C16—C170.5 (3)
N4—C4—C5—C6144.2 (2)N6—C16—C17—C18178.8 (2)
C3—C4—C5—C10141.3 (2)C15—C16—C17—C181.2 (3)
N4—C4—C5—C1036.6 (3)C16—C17—C18—C130.7 (3)
C10—C5—C6—C71.3 (3)C14—C13—C18—C170.6 (3)
C4—C5—C6—C7177.9 (2)C12—C13—C18—C17179.03 (19)
C5—C6—C7—C80.1 (4)C16—N6—C19—C2095.3 (3)
C6—C7—C8—C91.5 (4)C21—N6—C19—C2089.2 (3)
C7—C8—C9—C101.5 (4)C16—N6—C21—C2286.1 (3)
C8—C9—C10—C50.1 (3)C19—N6—C21—C2289.5 (3)
 

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