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In the title compound, C14H16ClN7O2, the triazole ring carries cyano and formamidine substituents and is bound via a methyl­ene bridge to a chloro­pyridine unit. There is evidence of significant electron delocalization in the triazolyl system. Intra­molecular O—H...O and inter­molecular C—H...N, C—H...O and O—H...N hydrogen bonds, together with strong π–π stacking inter­actions, stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604551X/sj2156sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604551X/sj2156Isup2.hkl
Contains datablock I

CCDC reference: 630473

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.142
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C12 .. 5.32 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C7 - C8 ... 1.42 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact N4 .. C10 .. 3.02 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N4 -C7 -C8 -N5 -82.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 C9 -C7 -C8 -N5 95.00 12.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 1997); software used to prepare material for publication: SHELXTL.

(E)—N2{3-[(6-Chloropyridin-3-yl)methyl]-5-cyano-3H-1,2,3-triazol-4-yl}- N1,N1-bis(2-hydroxyethyl)formamidine top
Crystal data top
C14H16ClN7O2F(000) = 728
Mr = 349.79Dx = 1.411 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3647 reflections
a = 7.6293 (9) Åθ = 2.5–27.1°
b = 8.1921 (9) ŵ = 0.26 mm1
c = 26.351 (3) ÅT = 298 K
β = 90.438 (2)°Block, colorless
V = 1646.9 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3558 independent reflections
Radiation source: fine-focus sealed tube2902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 99
Tmin = 0.927, Tmax = 0.951k = 1010
9222 measured reflectionsl = 3326
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.7964P]
where P = (Fo2 + 2Fc2)/3
3558 reflections(Δ/σ)max = 0.004
223 parametersΔρmax = 0.33 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
C10.2573 (3)0.0192 (3)1.01527 (8)0.0434 (5)
C20.2283 (3)0.1198 (3)0.98690 (9)0.0506 (6)
H20.23450.22301.00150.061*
C30.1901 (3)0.1000 (3)0.93636 (9)0.0496 (6)
H30.17170.19080.91580.059*
C40.1788 (3)0.0552 (3)0.91601 (8)0.0403 (5)
C50.2082 (3)0.1853 (3)0.94826 (8)0.0434 (5)
H50.20040.29010.93490.052*
C60.1429 (3)0.0840 (3)0.86023 (8)0.0471 (5)
H6A0.03470.02990.85050.057*
H6B0.12860.20010.85410.057*
C70.5305 (3)0.0232 (3)0.79287 (8)0.0416 (5)
C80.7032 (4)0.0204 (3)0.77298 (10)0.0524 (6)
C100.6143 (3)0.3195 (3)0.82597 (7)0.0386 (5)
H100.68960.26520.80410.046*
C110.8085 (3)0.5487 (3)0.81822 (10)0.0535 (6)
H11A0.76480.63880.79790.064*
H11B0.86530.47240.79550.064*
C120.9412 (4)0.6125 (4)0.85455 (11)0.0648 (7)
H12A1.03760.65840.83540.078*
H12B0.88880.70050.87380.078*
C130.5416 (3)0.5558 (3)0.87567 (9)0.0487 (6)
H13A0.42200.54460.86340.058*
H13B0.57170.67080.87470.058*
C140.5518 (4)0.4964 (3)0.92997 (9)0.0538 (6)
H14A0.46480.55380.94980.065*
H14B0.52290.38110.93070.065*
Cl10.31138 (10)0.00025 (9)1.07913 (2)0.0648 (2)
N10.2474 (2)0.1694 (2)0.99772 (7)0.0466 (5)
N20.2867 (2)0.0216 (2)0.82938 (7)0.0418 (4)
N30.2798 (3)0.1318 (2)0.81001 (7)0.0508 (5)
N40.4279 (3)0.1588 (2)0.78786 (7)0.0501 (5)
C90.4411 (3)0.0950 (3)0.82036 (7)0.0374 (5)
N50.8428 (4)0.0199 (4)0.75797 (12)0.0833 (8)
N60.4708 (2)0.2476 (2)0.83927 (6)0.0398 (4)
N70.6584 (3)0.4662 (2)0.84198 (7)0.0427 (4)
O10.7192 (3)0.5192 (2)0.95303 (7)0.0582 (5)
H10.726 (4)0.615 (4)0.9632 (13)0.087*
O21.0088 (3)0.4969 (3)0.88861 (10)0.0794 (7)
H2A0.914 (6)0.483 (5)0.9097 (17)0.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0398 (12)0.0539 (14)0.0365 (11)0.0009 (10)0.0023 (9)0.0002 (10)
C20.0563 (15)0.0441 (13)0.0515 (13)0.0043 (11)0.0041 (11)0.0037 (10)
C30.0542 (14)0.0488 (13)0.0457 (13)0.0099 (11)0.0028 (10)0.0085 (10)
C40.0300 (10)0.0541 (13)0.0369 (11)0.0074 (9)0.0048 (8)0.0039 (9)
C50.0436 (12)0.0454 (12)0.0414 (12)0.0042 (10)0.0027 (9)0.0004 (9)
C60.0365 (12)0.0654 (15)0.0394 (12)0.0077 (11)0.0004 (9)0.0031 (11)
C70.0506 (13)0.0433 (12)0.0310 (10)0.0036 (10)0.0009 (9)0.0017 (9)
C80.0592 (16)0.0488 (14)0.0493 (14)0.0030 (11)0.0071 (11)0.0005 (11)
C100.0428 (12)0.0436 (12)0.0293 (10)0.0022 (9)0.0005 (8)0.0017 (8)
C110.0569 (15)0.0522 (14)0.0515 (14)0.0160 (12)0.0064 (11)0.0101 (11)
C120.0562 (16)0.0665 (17)0.0719 (18)0.0195 (14)0.0080 (13)0.0063 (14)
C130.0504 (14)0.0402 (12)0.0555 (14)0.0028 (10)0.0026 (11)0.0038 (10)
C140.0633 (16)0.0512 (14)0.0471 (13)0.0080 (12)0.0140 (12)0.0077 (11)
Cl10.0767 (5)0.0770 (5)0.0405 (3)0.0054 (3)0.0090 (3)0.0032 (3)
N10.0511 (11)0.0471 (11)0.0415 (10)0.0022 (9)0.0026 (8)0.0053 (8)
N20.0440 (10)0.0484 (11)0.0328 (9)0.0113 (8)0.0010 (7)0.0033 (8)
N30.0613 (13)0.0509 (11)0.0402 (10)0.0167 (10)0.0018 (9)0.0048 (8)
N40.0648 (13)0.0465 (11)0.0389 (10)0.0087 (10)0.0022 (9)0.0040 (8)
C90.0419 (11)0.0440 (11)0.0263 (9)0.0061 (9)0.0014 (8)0.0025 (8)
N50.0652 (17)0.088 (2)0.097 (2)0.0102 (14)0.0264 (15)0.0041 (15)
N60.0422 (10)0.0423 (10)0.0349 (9)0.0051 (8)0.0001 (7)0.0002 (8)
N70.0479 (11)0.0437 (10)0.0366 (9)0.0103 (8)0.0017 (8)0.0026 (8)
O10.0747 (13)0.0546 (11)0.0453 (10)0.0036 (9)0.0006 (8)0.0073 (8)
O20.0562 (13)0.1039 (18)0.0780 (15)0.0102 (11)0.0044 (10)0.0070 (12)
Geometric parameters (Å, º) top
C1—N11.316 (3)C11—N71.474 (3)
C1—C21.379 (3)C11—C121.483 (4)
C1—Cl11.737 (2)C11—H11A0.9700
C2—C31.371 (3)C11—H11B0.9700
C2—H20.9300C12—O21.400 (4)
C3—C41.382 (3)C12—H12A0.9700
C3—H30.9300C12—H12B0.9700
C4—C51.380 (3)C13—N71.460 (3)
C4—C61.512 (3)C13—C141.513 (3)
C5—N11.341 (3)C13—H13A0.9700
C5—H50.9300C13—H13B0.9700
C6—N21.463 (3)C14—O11.423 (3)
C6—H6A0.9700C14—H14A0.9700
C6—H6B0.9700C14—H14B0.9700
C7—N41.365 (3)N2—C91.345 (3)
C7—C91.391 (3)N2—N31.357 (3)
C7—C81.422 (4)N3—N41.295 (3)
C8—N51.139 (4)C9—N61.364 (3)
C10—N61.294 (3)O1—H10.83 (4)
C10—N71.316 (3)O2—H2A0.92 (5)
C10—H100.9300
N1—C1—C2125.0 (2)O2—C12—C11114.9 (2)
N1—C1—Cl1116.02 (17)O2—C12—H12A108.5
C2—C1—Cl1119.02 (18)C11—C12—H12A108.5
C3—C2—C1117.4 (2)O2—C12—H12B108.5
C3—C2—H2121.3C11—C12—H12B108.5
C1—C2—H2121.3H12A—C12—H12B107.5
C2—C3—C4119.9 (2)N7—C13—C14112.7 (2)
C2—C3—H3120.1N7—C13—H13A109.0
C4—C3—H3120.1C14—C13—H13A109.0
C5—C4—C3117.5 (2)N7—C13—H13B109.0
C5—C4—C6120.4 (2)C14—C13—H13B109.0
C3—C4—C6122.1 (2)H13A—C13—H13B107.8
N1—C5—C4123.9 (2)O1—C14—C13113.7 (2)
N1—C5—H5118.1O1—C14—H14A108.8
C4—C5—H5118.1C13—C14—H14A108.8
N2—C6—C4110.76 (19)O1—C14—H14B108.8
N2—C6—H6A109.5C13—C14—H14B108.8
C4—C6—H6A109.5H14A—C14—H14B107.7
N2—C6—H6B109.5C1—N1—C5116.34 (19)
C4—C6—H6B109.5C9—N2—N3112.26 (18)
H6A—C6—H6B108.1C9—N2—C6127.13 (19)
N4—C7—C9109.5 (2)N3—N2—C6120.35 (18)
N4—C7—C8120.7 (2)N4—N3—N2107.24 (18)
C9—C7—C8129.8 (2)N3—N4—C7108.60 (19)
N5—C8—C7178.5 (3)N2—C9—N6119.20 (19)
N6—C10—N7122.9 (2)N2—C9—C7102.38 (18)
N6—C10—H10118.5N6—C9—C7138.4 (2)
N7—C10—H10118.5C10—N6—C9117.17 (18)
N7—C11—C12114.6 (2)C10—N7—C13119.86 (19)
N7—C11—H11A108.6C10—N7—C11118.69 (19)
C12—C11—H11A108.6C13—N7—C11120.5 (2)
N7—C11—H11B108.6C14—O1—H1108 (2)
C12—C11—H11B108.6C12—O2—H2A101 (3)
H11A—C11—H11B107.6
N1—C1—C2—C31.5 (4)N2—N3—N4—C70.0 (2)
Cl1—C1—C2—C3178.46 (18)C9—C7—N4—N30.7 (3)
C1—C2—C3—C41.1 (4)C8—C7—N4—N3178.5 (2)
C2—C3—C4—C50.3 (3)N3—N2—C9—N6177.39 (17)
C2—C3—C4—C6178.0 (2)C6—N2—C9—N63.2 (3)
C3—C4—C5—N10.3 (3)N3—N2—C9—C71.1 (2)
C6—C4—C5—N1177.39 (19)C6—N2—C9—C7175.2 (2)
C5—C4—C6—N2112.9 (2)N4—C7—C9—N21.0 (2)
C3—C4—C6—N264.7 (3)C8—C7—C9—N2178.6 (2)
N4—C7—C8—N582 (13)N4—C7—C9—N6176.9 (2)
C9—C7—C8—N595 (12)C8—C7—C9—N60.6 (4)
N7—C11—C12—O254.9 (3)N7—C10—N6—C9179.45 (19)
N7—C13—C14—O163.3 (3)N2—C9—N6—C10173.99 (18)
C2—C1—N1—C50.9 (3)C7—C9—N6—C108.3 (4)
Cl1—C1—N1—C5179.06 (16)N6—C10—N7—C130.9 (3)
C4—C5—N1—C10.0 (3)N6—C10—N7—C11169.9 (2)
C4—C6—N2—C980.3 (3)C14—C13—N7—C1077.6 (3)
C4—C6—N2—N393.4 (2)C14—C13—N7—C11113.7 (2)
C9—N2—N3—N40.7 (2)C12—C11—N7—C10128.8 (2)
C6—N2—N3—N4175.34 (19)C12—C11—N7—C1362.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.92 (5)1.91 (5)2.802 (3)164 (4)
C12—H12A···N3i0.972.613.533 (3)158
C5—H5···O2ii0.932.543.356 (3)146
O1—H1···N1iii0.83 (4)2.05 (4)2.873 (3)168 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+2.
 

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