(E)-N²-{3-[(6-Chloro­pyridin-3-yl)meth­yl]-5-cyano-3H-1,2,3-triazol-4-yl}-N¹,N¹-bis­(2-hydroxy­ethyl)formamidine

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.

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

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

Crystal data

C14H16ClN7O2	F(000) = 728
Mr = 349.79	Dx = 1.411 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3647 reflections
a = 7.6293 (9) Å	θ = 2.5–27.1°
b = 8.1921 (9) Å	µ = 0.26 mm^−1
c = 26.351 (3) Å	T = 298 K
β = 90.438 (2)°	Block, colorless
V = 1646.9 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3558 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.927, Tmax = 0.951	k = −10→10
9222 measured reflections	l = −33→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.7964P] where P = (Fo^2 + 2Fc^2)/3
3558 reflections	(Δ/σ)max = 0.004
223 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2573 (3)	0.0192 (3)	1.01527 (8)	0.0434 (5)
C2	0.2283 (3)	−0.1198 (3)	0.98690 (9)	0.0506 (6)
H2	0.2345	−0.2230	1.0015	0.061*
C3	0.1901 (3)	−0.1000 (3)	0.93636 (9)	0.0496 (6)
H3	0.1717	−0.1908	0.9158	0.059*
C4	0.1788 (3)	0.0552 (3)	0.91601 (8)	0.0403 (5)
C5	0.2082 (3)	0.1853 (3)	0.94826 (8)	0.0434 (5)
H5	0.2004	0.2901	0.9349	0.052*
C6	0.1429 (3)	0.0840 (3)	0.86023 (8)	0.0471 (5)
H6A	0.0347	0.0299	0.8505	0.057*
H6B	0.1286	0.2001	0.8541	0.057*
C7	0.5305 (3)	−0.0232 (3)	0.79287 (8)	0.0416 (5)
C8	0.7032 (4)	−0.0204 (3)	0.77298 (10)	0.0524 (6)
C10	0.6143 (3)	0.3195 (3)	0.82597 (7)	0.0386 (5)
H10	0.6896	0.2652	0.8041	0.046*
C11	0.8085 (3)	0.5487 (3)	0.81822 (10)	0.0535 (6)
H11A	0.7648	0.6388	0.7979	0.064*
H11B	0.8653	0.4724	0.7955	0.064*
C12	0.9412 (4)	0.6125 (4)	0.85455 (11)	0.0648 (7)
H12A	1.0376	0.6584	0.8354	0.078*
H12B	0.8888	0.7005	0.8738	0.078*
C13	0.5416 (3)	0.5558 (3)	0.87567 (9)	0.0487 (6)
H13A	0.4220	0.5446	0.8634	0.058*
H13B	0.5717	0.6708	0.8747	0.058*
C14	0.5518 (4)	0.4964 (3)	0.92997 (9)	0.0538 (6)
H14A	0.4648	0.5538	0.9498	0.065*
H14B	0.5229	0.3811	0.9307	0.065*
Cl1	0.31138 (10)	−0.00025 (9)	1.07913 (2)	0.0648 (2)
N1	0.2474 (2)	0.1694 (2)	0.99772 (7)	0.0466 (5)
N2	0.2867 (2)	0.0216 (2)	0.82938 (7)	0.0418 (4)
N3	0.2798 (3)	−0.1318 (2)	0.81001 (7)	0.0508 (5)
N4	0.4279 (3)	−0.1588 (2)	0.78786 (7)	0.0501 (5)
C9	0.4411 (3)	0.0950 (3)	0.82036 (7)	0.0374 (5)
N5	0.8428 (4)	−0.0199 (4)	0.75797 (12)	0.0833 (8)
N6	0.4708 (2)	0.2476 (2)	0.83927 (6)	0.0398 (4)
N7	0.6584 (3)	0.4662 (2)	0.84198 (7)	0.0427 (4)
O1	0.7192 (3)	0.5192 (2)	0.95303 (7)	0.0582 (5)
H1	0.726 (4)	0.615 (4)	0.9632 (13)	0.087*
O2	1.0088 (3)	0.4969 (3)	0.88861 (10)	0.0794 (7)
H2A	0.914 (6)	0.483 (5)	0.9097 (17)	0.119*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0398 (12)	0.0539 (14)	0.0365 (11)	−0.0009 (10)	0.0023 (9)	−0.0002 (10)
C2	0.0563 (15)	0.0441 (13)	0.0515 (13)	−0.0043 (11)	0.0041 (11)	0.0037 (10)
C3	0.0542 (14)	0.0488 (13)	0.0457 (13)	−0.0099 (11)	0.0028 (10)	−0.0085 (10)
C4	0.0300 (10)	0.0541 (13)	0.0369 (11)	−0.0074 (9)	0.0048 (8)	−0.0039 (9)
C5	0.0436 (12)	0.0454 (12)	0.0414 (12)	−0.0042 (10)	0.0027 (9)	0.0004 (9)
C6	0.0365 (12)	0.0654 (15)	0.0394 (12)	−0.0077 (11)	0.0004 (9)	−0.0031 (11)
C7	0.0506 (13)	0.0433 (12)	0.0310 (10)	−0.0036 (10)	0.0009 (9)	0.0017 (9)
C8	0.0592 (16)	0.0488 (14)	0.0493 (14)	0.0030 (11)	0.0071 (11)	−0.0005 (11)
C10	0.0428 (12)	0.0436 (12)	0.0293 (10)	−0.0022 (9)	−0.0005 (8)	0.0017 (8)
C11	0.0569 (15)	0.0522 (14)	0.0515 (14)	−0.0160 (12)	0.0064 (11)	0.0101 (11)
C12	0.0562 (16)	0.0665 (17)	0.0719 (18)	−0.0195 (14)	0.0080 (13)	−0.0063 (14)
C13	0.0504 (14)	0.0402 (12)	0.0555 (14)	−0.0028 (10)	−0.0026 (11)	−0.0038 (10)
C14	0.0633 (16)	0.0512 (14)	0.0471 (13)	−0.0080 (12)	0.0140 (12)	−0.0077 (11)
Cl1	0.0767 (5)	0.0770 (5)	0.0405 (3)	0.0054 (3)	−0.0090 (3)	0.0032 (3)
N1	0.0511 (11)	0.0471 (11)	0.0415 (10)	−0.0022 (9)	−0.0026 (8)	−0.0053 (8)
N2	0.0440 (10)	0.0484 (11)	0.0328 (9)	−0.0113 (8)	0.0010 (7)	−0.0033 (8)
N3	0.0613 (13)	0.0509 (11)	0.0402 (10)	−0.0167 (10)	0.0018 (9)	−0.0048 (8)
N4	0.0648 (13)	0.0465 (11)	0.0389 (10)	−0.0087 (10)	0.0022 (9)	−0.0040 (8)
C9	0.0419 (11)	0.0440 (11)	0.0263 (9)	−0.0061 (9)	−0.0014 (8)	0.0025 (8)
N5	0.0652 (17)	0.088 (2)	0.097 (2)	0.0102 (14)	0.0264 (15)	0.0041 (15)
N6	0.0422 (10)	0.0423 (10)	0.0349 (9)	−0.0051 (8)	−0.0001 (7)	−0.0002 (8)
N7	0.0479 (11)	0.0437 (10)	0.0366 (9)	−0.0103 (8)	0.0017 (8)	0.0026 (8)
O1	0.0747 (13)	0.0546 (11)	0.0453 (10)	−0.0036 (9)	−0.0006 (8)	−0.0073 (8)
O2	0.0562 (13)	0.1039 (18)	0.0780 (15)	0.0102 (11)	−0.0044 (10)	0.0070 (12)

Geometric parameters (Å, º)

C1—N1	1.316 (3)	C11—N7	1.474 (3)
C1—C2	1.379 (3)	C11—C12	1.483 (4)
C1—Cl1	1.737 (2)	C11—H11A	0.9700
C2—C3	1.371 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—O2	1.400 (4)
C3—C4	1.382 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.380 (3)	C13—N7	1.460 (3)
C4—C6	1.512 (3)	C13—C14	1.513 (3)
C5—N1	1.341 (3)	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700
C6—N2	1.463 (3)	C14—O1	1.423 (3)
C6—H6A	0.9700	C14—H14A	0.9700
C6—H6B	0.9700	C14—H14B	0.9700
C7—N4	1.365 (3)	N2—C9	1.345 (3)
C7—C9	1.391 (3)	N2—N3	1.357 (3)
C7—C8	1.422 (4)	N3—N4	1.295 (3)
C8—N5	1.139 (4)	C9—N6	1.364 (3)
C10—N6	1.294 (3)	O1—H1	0.83 (4)
C10—N7	1.316 (3)	O2—H2A	0.92 (5)
C10—H10	0.9300
N1—C1—C2	125.0 (2)	O2—C12—C11	114.9 (2)
N1—C1—Cl1	116.02 (17)	O2—C12—H12A	108.5
C2—C1—Cl1	119.02 (18)	C11—C12—H12A	108.5
C3—C2—C1	117.4 (2)	O2—C12—H12B	108.5
C3—C2—H2	121.3	C11—C12—H12B	108.5
C1—C2—H2	121.3	H12A—C12—H12B	107.5
C2—C3—C4	119.9 (2)	N7—C13—C14	112.7 (2)
C2—C3—H3	120.1	N7—C13—H13A	109.0
C4—C3—H3	120.1	C14—C13—H13A	109.0
C5—C4—C3	117.5 (2)	N7—C13—H13B	109.0
C5—C4—C6	120.4 (2)	C14—C13—H13B	109.0
C3—C4—C6	122.1 (2)	H13A—C13—H13B	107.8
N1—C5—C4	123.9 (2)	O1—C14—C13	113.7 (2)
N1—C5—H5	118.1	O1—C14—H14A	108.8
C4—C5—H5	118.1	C13—C14—H14A	108.8
N2—C6—C4	110.76 (19)	O1—C14—H14B	108.8
N2—C6—H6A	109.5	C13—C14—H14B	108.8
C4—C6—H6A	109.5	H14A—C14—H14B	107.7
N2—C6—H6B	109.5	C1—N1—C5	116.34 (19)
C4—C6—H6B	109.5	C9—N2—N3	112.26 (18)
H6A—C6—H6B	108.1	C9—N2—C6	127.13 (19)
N4—C7—C9	109.5 (2)	N3—N2—C6	120.35 (18)
N4—C7—C8	120.7 (2)	N4—N3—N2	107.24 (18)
C9—C7—C8	129.8 (2)	N3—N4—C7	108.60 (19)
N5—C8—C7	178.5 (3)	N2—C9—N6	119.20 (19)
N6—C10—N7	122.9 (2)	N2—C9—C7	102.38 (18)
N6—C10—H10	118.5	N6—C9—C7	138.4 (2)
N7—C10—H10	118.5	C10—N6—C9	117.17 (18)
N7—C11—C12	114.6 (2)	C10—N7—C13	119.86 (19)
N7—C11—H11A	108.6	C10—N7—C11	118.69 (19)
C12—C11—H11A	108.6	C13—N7—C11	120.5 (2)
N7—C11—H11B	108.6	C14—O1—H1	108 (2)
C12—C11—H11B	108.6	C12—O2—H2A	101 (3)
H11A—C11—H11B	107.6
N1—C1—C2—C3	1.5 (4)	N2—N3—N4—C7	0.0 (2)
Cl1—C1—C2—C3	−178.46 (18)	C9—C7—N4—N3	0.7 (3)
C1—C2—C3—C4	−1.1 (4)	C8—C7—N4—N3	178.5 (2)
C2—C3—C4—C5	0.3 (3)	N3—N2—C9—N6	−177.39 (17)
C2—C3—C4—C6	178.0 (2)	C6—N2—C9—N6	−3.2 (3)
C3—C4—C5—N1	0.3 (3)	N3—N2—C9—C7	1.1 (2)
C6—C4—C5—N1	−177.39 (19)	C6—N2—C9—C7	175.2 (2)
C5—C4—C6—N2	112.9 (2)	N4—C7—C9—N2	−1.0 (2)
C3—C4—C6—N2	−64.7 (3)	C8—C7—C9—N2	−178.6 (2)
N4—C7—C8—N5	−82 (13)	N4—C7—C9—N6	176.9 (2)
C9—C7—C8—N5	95 (12)	C8—C7—C9—N6	−0.6 (4)
N7—C11—C12—O2	54.9 (3)	N7—C10—N6—C9	−179.45 (19)
N7—C13—C14—O1	63.3 (3)	N2—C9—N6—C10	−173.99 (18)
C2—C1—N1—C5	−0.9 (3)	C7—C9—N6—C10	8.3 (4)
Cl1—C1—N1—C5	179.06 (16)	N6—C10—N7—C13	−0.9 (3)
C4—C5—N1—C1	0.0 (3)	N6—C10—N7—C11	−169.9 (2)
C4—C6—N2—C9	−80.3 (3)	C14—C13—N7—C10	77.6 (3)
C4—C6—N2—N3	93.4 (2)	C14—C13—N7—C11	−113.7 (2)
C9—N2—N3—N4	−0.7 (2)	C12—C11—N7—C10	−128.8 (2)
C6—N2—N3—N4	−175.34 (19)	C12—C11—N7—C13	62.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.92 (5)	1.91 (5)	2.802 (3)	164 (4)
C12—H12A···N3^i	0.97	2.61	3.533 (3)	158
C5—H5···O2^ii	0.93	2.54	3.356 (3)	146
O1—H1···N1^iii	0.83 (4)	2.05 (4)	2.873 (3)	168 (3)

Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+2.