4-(m-Chloro­benzyl­amino)-3-methyl-4,5-di­hydro-1H-1,2,4-triazol-5-one

The title compound, C₁₀H₁₁ClN₄O, displays the characteristic features of 1,2,4-triazole derivatives. The crystal structure is stabilized by N—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.062
• wR factor = 0.205
• Data-to-parameter ratio = 22.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N1     -   H1     ...          ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).

(I)

Crystal data

C10H11ClN4O	F(000) = 496
Mr = 238.68	Dx = 1.360 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14391 reflections
a = 14.3423 (15) Å	θ = 1.7–29.3°
b = 5.8708 (3) Å	µ = 0.31 mm^−1
c = 15.2730 (14) Å	T = 293 K
β = 114.963 (7)°	Prismatic, colourless
V = 1165.86 (17) Å^3	0.60 × 0.46 × 0.28 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	3218 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 6.67 pixels mm^-1	θmax = 29.4°, θmin = 2.7°
rotation method scans	h = −19→17
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = 0→8
Tmin = 0.839, Tmax = 0.923	l = 0→20
3218 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.205	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.1356P)^2] where P = (Fo^2 + 2Fc^2)/3
3218 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.43 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
C3	0.8370 (4)	0.0088 (8)	0.8114 (4)	0.1042 (13)
H3	0.8882	−0.0928	0.8149	0.125*
C4	0.8617 (3)	0.1920 (7)	0.8764 (3)	0.0935 (11)
H4	0.9288	0.2121	0.9226	0.112*
O1	0.96137 (14)	0.4083 (3)	1.16108 (13)	0.0729 (5)
C2	0.7405 (4)	−0.0218 (6)	0.7443 (3)	0.0943 (11)
H2	0.7249	−0.1444	0.7020	0.113*
C7	0.8070 (3)	0.5315 (5)	0.9425 (2)	0.0869 (10)
H7A	0.8807	0.5448	0.9804	0.104*
H7B	0.7824	0.6739	0.9084	0.104*
C10	0.89134 (17)	0.2665 (4)	1.13455 (14)	0.0510 (5)
C5	0.7855 (2)	0.3420 (5)	0.87106 (18)	0.0658 (7)
N3	0.88941 (15)	0.0553 (3)	1.16510 (13)	0.0572 (5)
H3A	0.9416	−0.0103	1.2095	0.069*
C1	0.6664 (3)	0.1265 (5)	0.73876 (19)	0.0751 (8)
C6	0.6870 (2)	0.3086 (5)	0.80052 (18)	0.0664 (7)
H6	0.6348	0.4095	0.7949	0.080*
N2	0.79365 (13)	0.2948 (3)	1.06236 (12)	0.0463 (4)
N1	0.75691 (18)	0.4909 (3)	1.00719 (13)	0.0641 (6)
H1	0.7103	0.5779	1.0107	0.077*
N4	0.79494 (16)	−0.0470 (3)	1.11810 (14)	0.0587 (5)
C8	0.73907 (17)	0.1019 (3)	1.05554 (15)	0.0479 (5)
Cl1	0.54065 (9)	0.0838 (2)	0.65249 (7)	0.1302 (5)
C9	0.6299 (2)	0.0695 (5)	0.9878 (2)	0.0744 (8)
H9A	0.6051	0.2038	0.9491	0.112*
H9B	0.5899	0.0423	1.0238	0.112*
H9C	0.6240	−0.0587	0.9468	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.120 (3)	0.104 (3)	0.129 (3)	0.030 (3)	0.092 (3)	0.034 (3)
C4	0.0710 (18)	0.116 (3)	0.099 (2)	−0.0012 (19)	0.0410 (17)	0.039 (2)
O1	0.0712 (11)	0.0676 (12)	0.0576 (9)	−0.0243 (9)	0.0056 (8)	−0.0055 (8)
C2	0.150 (3)	0.078 (2)	0.092 (2)	0.003 (2)	0.087 (3)	0.0044 (18)
C7	0.116 (2)	0.0664 (17)	0.0601 (15)	−0.0331 (17)	0.0200 (16)	0.0120 (13)
C10	0.0567 (12)	0.0469 (12)	0.0383 (9)	−0.0031 (10)	0.0092 (9)	−0.0048 (9)
C5	0.0733 (16)	0.0670 (15)	0.0564 (13)	−0.0108 (13)	0.0268 (12)	0.0164 (12)
N3	0.0581 (11)	0.0478 (11)	0.0489 (10)	0.0041 (9)	0.0062 (8)	0.0058 (8)
C1	0.100 (2)	0.0775 (19)	0.0546 (14)	−0.0116 (17)	0.0393 (15)	−0.0046 (13)
C6	0.0752 (16)	0.0672 (16)	0.0564 (13)	0.0040 (13)	0.0273 (12)	0.0021 (12)
N2	0.0555 (10)	0.0349 (8)	0.0394 (8)	−0.0005 (7)	0.0110 (7)	0.0006 (6)
N1	0.0855 (14)	0.0365 (9)	0.0509 (10)	0.0052 (9)	0.0099 (10)	0.0060 (8)
N4	0.0668 (12)	0.0443 (10)	0.0543 (10)	−0.0054 (9)	0.0151 (9)	0.0039 (8)
C8	0.0554 (12)	0.0383 (10)	0.0469 (10)	−0.0027 (9)	0.0186 (9)	−0.0014 (8)
Cl1	0.1346 (9)	0.1493 (11)	0.0759 (6)	−0.0396 (8)	0.0143 (6)	−0.0252 (6)
C9	0.0547 (14)	0.0764 (18)	0.0755 (17)	−0.0105 (13)	0.0113 (12)	0.0056 (14)

Geometric parameters (Å, º)

C3—C2	1.341 (6)	C5—C6	1.381 (4)
C3—C4	1.404 (6)	N3—N4	1.375 (3)
C3—H3	0.9300	N3—H3A	0.8600
C4—C5	1.379 (5)	C1—C6	1.373 (4)
C4—H4	0.9300	C1—Cl1	1.746 (3)
O1—C10	1.234 (3)	C6—H6	0.9300
C2—C1	1.349 (5)	N2—C8	1.356 (3)
C2—H2	0.9300	N2—N1	1.392 (2)
C7—N1	1.465 (4)	N1—H1	0.8600
C7—C5	1.497 (4)	N4—C8	1.293 (3)
C7—H7A	0.9700	C8—C9	1.480 (3)
C7—H7B	0.9700	C9—H9A	0.9600
C10—N3	1.330 (3)	C9—H9B	0.9600
C10—N2	1.379 (3)	C9—H9C	0.9600
C2—C3—C4	120.9 (4)	N4—N3—H3A	123.6
C2—C3—H3	119.5	C2—C1—C6	121.6 (3)
C4—C3—H3	119.5	C2—C1—Cl1	119.4 (3)
C5—C4—C3	119.4 (3)	C6—C1—Cl1	119.0 (3)
C5—C4—H4	120.3	C1—C6—C5	119.9 (3)
C3—C4—H4	120.3	C1—C6—H6	120.0
C3—C2—C1	119.5 (4)	C5—C6—H6	120.0
C3—C2—H2	120.2	C8—N2—C10	108.65 (17)
C1—C2—H2	120.2	C8—N2—N1	125.85 (18)
N1—C7—C5	111.2 (2)	C10—N2—N1	125.49 (19)
N1—C7—H7A	109.4	N2—N1—C7	112.0 (2)
C5—C7—H7A	109.4	N2—N1—H1	124.0
N1—C7—H7B	109.4	C7—N1—H1	124.0
C5—C7—H7B	109.4	C8—N4—N3	104.91 (18)
H7A—C7—H7B	108.0	N4—C8—N2	110.50 (19)
O1—C10—N3	130.5 (2)	N4—C8—C9	124.9 (2)
O1—C10—N2	126.4 (2)	N2—C8—C9	124.6 (2)
N3—C10—N2	103.19 (18)	C8—C9—H9A	109.5
C4—C5—C6	118.6 (3)	C8—C9—H9B	109.5
C4—C5—C7	121.1 (3)	H9A—C9—H9B	109.5
C6—C5—C7	120.2 (3)	C8—C9—H9C	109.5
C10—N3—N4	112.71 (18)	H9A—C9—H9C	109.5
C10—N3—H3A	123.6	H9B—C9—H9C	109.5
C2—C3—C4—C5	0.1 (5)	O1—C10—N2—C8	−179.4 (2)
C4—C3—C2—C1	0.5 (5)	N3—C10—N2—C8	1.2 (2)
C3—C4—C5—C6	−1.0 (4)	O1—C10—N2—N1	−0.6 (4)
C3—C4—C5—C7	176.3 (3)	N3—C10—N2—N1	−180.0 (2)
N1—C7—C5—C4	−109.9 (3)	C8—N2—N1—C7	−113.2 (3)
N1—C7—C5—C6	67.4 (3)	C10—N2—N1—C7	68.2 (3)
O1—C10—N3—N4	178.6 (2)	C5—C7—N1—N2	62.5 (3)
N2—C10—N3—N4	−2.0 (2)	C10—N3—N4—C8	2.0 (3)
C3—C2—C1—C6	−0.3 (5)	N3—N4—C8—N2	−1.1 (2)
C3—C2—C1—Cl1	−179.1 (3)	N3—N4—C8—C9	−179.5 (2)
C2—C1—C6—C5	−0.6 (4)	C10—N2—C8—N4	0.0 (3)
Cl1—C1—C6—C5	178.2 (2)	N1—N2—C8—N4	−178.8 (2)
C4—C5—C6—C1	1.2 (4)	C10—N2—C8—C9	178.3 (2)
C7—C5—C6—C1	−176.1 (2)	N1—N2—C8—C9	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1^i	0.86	1.94	2.752 (2)	158

Symmetry code: (i) −x+2, y−1/2, −z+5/2.