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

The conformation of the title compound, C₁₅H₁₃ClN₄O, can be described in terms of four essentially planar fragments. The triazole ring is planar within 0.008 Å, and its plane, while being almost parallel to the benzene plane of the benzyl­amino group [dihedral angle 2.95 (14)°], forms a dihedral angle of 16.43 (12)° with the plane of its 3-phenyl substituent. The four-atom bridge (triazole)N—N(H)—C(H₂)—C(C₆H₄Cl), linking the triazole moiety with the chloro­phenyl group, is also almost planar, the N—N—C—C torsion angle being −178.82 (13)°. Its mean plane is approximately normal to the triazole and chloro­phenyl planes [dihedral angles 107.08 (10) and 108.81 (10)°, respectively]. Two independent N—H...O bonds link the mol­ecules into infinite chains running along the b axis of the crystal.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.126
• Data-to-parameter ratio = 9.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          colourless'

CRYSC_01  Alert C No recognised colour has been given for crystal colour.

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.80
         From the CIF: _reflns_number_total               2327
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2491
         Completeness (_total/calc)             93.42%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

Crystal data

C15H13ClN4O	Z = 2
Mr = 300.74	F(000) = 312
Triclinic, P1	Dx = 1.385 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1819 (10) Å	Cell parameters from 6723 reflections
b = 7.4204 (9) Å	θ = 2.7–29.5°
c = 14.3295 (19) Å	µ = 0.27 mm^−1
α = 88.224 (10)°	T = 293 K
β = 80.974 (11)°	Rectangular, colourless'
γ = 72.945 (10)°	0.80 × 0.48 × 0.25 mm
V = 720.94 (16) Å^3

Data collection

Stoe IPDS 2 diffractometer	1975 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.044
Plane graphite monochromator	θmax = 24.8°, θmin = 2.9°
Detector resolution: 6.67 pixels mm^-1	h = −8→8
φ scans	k = −8→8
2327 measured reflections	l = 0→16
2327 independent 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.126	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2327 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.18 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
Cl1	0.33854 (10)	0.04550 (8)	0.63609 (4)	0.0819 (3)
O1	0.07517 (18)	−0.77037 (17)	0.99174 (7)	0.0507 (3)
N1	0.0434 (2)	−0.49176 (19)	0.84166 (9)	0.0437 (3)
N2	−0.0262 (2)	−0.65076 (19)	0.84888 (9)	0.0432 (3)
N3	−0.0855 (2)	−0.9054 (2)	0.89720 (10)	0.0520 (4)
N4	−0.1552 (2)	−0.8679 (2)	0.81252 (10)	0.0533 (4)
C1	0.4266 (3)	−0.3349 (3)	0.88282 (15)	0.0624 (5)
C2	0.4972 (3)	−0.1803 (4)	0.87564 (17)	0.0708 (6)
C3	0.4711 (3)	−0.0630 (3)	0.80058 (16)	0.0611 (5)
C4	0.3699 (3)	−0.0997 (3)	0.73327 (13)	0.0526 (4)
C5	0.2985 (2)	−0.2542 (2)	0.73927 (12)	0.0478 (4)
C6	0.3284 (2)	−0.3744 (2)	0.81405 (12)	0.0473 (4)
C7	0.2599 (3)	−0.5480 (3)	0.81911 (15)	0.0574 (5)
C8	−0.0029 (2)	−0.7783 (2)	0.92144 (10)	0.0431 (4)
C9	−0.1181 (2)	−0.7124 (2)	0.78393 (11)	0.0454 (4)
C10	−0.1649 (2)	−0.6265 (3)	0.69367 (11)	0.0491 (4)
C11	−0.1725 (3)	−0.4417 (3)	0.67111 (13)	0.0554 (5)
C12	−0.2206 (3)	−0.3708 (4)	0.58469 (15)	0.0674 (6)
C13	−0.2632 (3)	−0.4811 (4)	0.52129 (15)	0.0755 (7)
C14	−0.2575 (4)	−0.6624 (5)	0.54343 (16)	0.0819 (7)
C15	−0.2090 (3)	−0.7354 (4)	0.62860 (14)	0.0682 (6)
H1	0.441 (4)	−0.407 (4)	0.932 (2)	0.092 (8)*
H2	0.569 (4)	−0.165 (4)	0.9248 (18)	0.088 (7)*
H3	0.527 (3)	0.051 (4)	0.7914 (16)	0.078 (6)*
H4	0.229 (3)	−0.271 (3)	0.6936 (15)	0.060 (5)*
H5	0.299 (3)	−0.619 (3)	0.7554 (16)	0.075 (6)*
H6	0.324 (4)	−0.639 (4)	0.8696 (18)	0.083 (7)*
H7	0.004 (3)	−0.435 (3)	0.8948 (14)	0.046 (5)*
H8	−0.094 (3)	−0.999 (3)	0.9231 (15)	0.055 (6)*
H9	−0.152 (3)	−0.368 (3)	0.7162 (15)	0.058 (5)*
H10	−0.230 (4)	−0.247 (5)	0.571 (2)	0.091 (8)*
H11	−0.301 (4)	−0.424 (4)	0.459 (2)	0.094 (8)*
H12	−0.287 (5)	−0.752 (5)	0.497 (2)	0.120 (10)*
H13	−0.190 (3)	−0.855 (4)	0.6403 (17)	0.069 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1031 (5)	0.0573 (4)	0.0828 (4)	−0.0261 (3)	−0.0065 (3)	0.0238 (3)
O1	0.0770 (8)	0.0471 (7)	0.0388 (6)	−0.0327 (6)	−0.0138 (5)	0.0060 (5)
N1	0.0565 (8)	0.0365 (7)	0.0433 (7)	−0.0224 (6)	−0.0072 (6)	0.0033 (6)
N2	0.0560 (7)	0.0410 (8)	0.0393 (6)	−0.0248 (6)	−0.0077 (5)	0.0053 (5)
N3	0.0749 (9)	0.0491 (9)	0.0458 (7)	−0.0381 (8)	−0.0141 (6)	0.0121 (6)
N4	0.0661 (8)	0.0589 (9)	0.0489 (7)	−0.0367 (7)	−0.0166 (6)	0.0092 (6)
C1	0.0682 (11)	0.0681 (14)	0.0553 (10)	−0.0242 (10)	−0.0160 (8)	0.0086 (9)
C2	0.0677 (11)	0.0781 (15)	0.0768 (13)	−0.0296 (11)	−0.0224 (10)	−0.0146 (11)
C3	0.0566 (10)	0.0503 (11)	0.0826 (13)	−0.0271 (9)	−0.0053 (9)	−0.0080 (10)
C4	0.0517 (9)	0.0414 (9)	0.0629 (10)	−0.0163 (8)	0.0012 (7)	0.0033 (8)
C5	0.0505 (8)	0.0469 (10)	0.0507 (9)	−0.0209 (7)	−0.0092 (7)	0.0002 (7)
C6	0.0470 (8)	0.0436 (9)	0.0534 (9)	−0.0189 (7)	−0.0033 (6)	0.0024 (7)
C7	0.0567 (10)	0.0425 (10)	0.0744 (12)	−0.0220 (8)	−0.0006 (9)	0.0040 (9)
C8	0.0559 (8)	0.0427 (9)	0.0363 (7)	−0.0248 (7)	−0.0043 (6)	0.0026 (6)
C9	0.0473 (8)	0.0509 (10)	0.0441 (8)	−0.0238 (7)	−0.0073 (6)	0.0017 (7)
C10	0.0424 (8)	0.0620 (11)	0.0456 (8)	−0.0194 (8)	−0.0073 (6)	0.0060 (7)
C11	0.0521 (9)	0.0594 (12)	0.0512 (9)	−0.0118 (8)	−0.0078 (7)	0.0078 (8)
C12	0.0570 (10)	0.0729 (15)	0.0644 (11)	−0.0089 (10)	−0.0092 (8)	0.0231 (10)
C13	0.0646 (11)	0.108 (2)	0.0539 (11)	−0.0225 (12)	−0.0197 (9)	0.0240 (12)
C14	0.0918 (15)	0.111 (2)	0.0571 (11)	−0.0431 (15)	−0.0308 (10)	0.0104 (12)
C15	0.0815 (13)	0.0804 (16)	0.0582 (11)	−0.0408 (12)	−0.0252 (9)	0.0088 (10)

Geometric parameters (Å, º)

Cl1—C4	1.736 (2)	C4—C5	1.382 (2)
O1—C8	1.2381 (19)	C5—C6	1.375 (3)
N1—N2	1.4054 (17)	C5—H4	0.91 (2)
N1—C7	1.472 (2)	C6—C7	1.504 (2)
N1—H7	0.850 (19)	C7—H5	1.02 (2)
N2—C8	1.380 (2)	C7—H6	1.04 (3)
N2—C9	1.381 (2)	C9—C10	1.467 (2)
N3—C8	1.332 (2)	C10—C15	1.383 (3)
N3—N4	1.374 (2)	C10—C11	1.386 (3)
N3—H8	0.79 (2)	C11—C12	1.385 (3)
N4—C9	1.299 (2)	C11—H9	0.92 (2)
C1—C2	1.379 (3)	C12—C13	1.368 (4)
C1—C6	1.382 (3)	C12—H10	0.92 (3)
C1—H1	0.87 (3)	C13—C14	1.363 (4)
C2—C3	1.364 (3)	C13—H11	1.02 (3)
C2—H2	0.97 (3)	C14—C15	1.373 (3)
C3—C4	1.373 (3)	C14—H12	1.04 (3)
C3—H3	1.03 (2)	C15—H13	0.87 (3)
N2—N1—C7	110.79 (13)	N1—C7—H5	107.8 (12)
N2—N1—H7	106.3 (12)	C6—C7—H5	110.8 (13)
C7—N1—H7	111.0 (12)	N1—C7—H6	111.2 (13)
C8—N2—C9	108.47 (12)	C6—C7—H6	110.0 (14)
C8—N2—N1	124.60 (12)	H5—C7—H6	108.0 (19)
C9—N2—N1	126.84 (13)	O1—C8—N3	129.87 (16)
C8—N3—N4	113.12 (15)	O1—C8—N2	126.78 (13)
C8—N3—H8	129.1 (15)	N3—C8—N2	103.34 (13)
N4—N3—H8	117.7 (15)	N4—C9—N2	109.72 (14)
C9—N4—N3	105.32 (13)	N4—C9—C10	122.54 (14)
C2—C1—C6	120.7 (2)	N2—C9—C10	127.70 (14)
C2—C1—H1	119.7 (19)	C15—C10—C11	118.40 (18)
C6—C1—H1	119.5 (19)	C15—C10—C9	117.78 (18)
C3—C2—C1	120.63 (19)	C11—C10—C9	123.80 (16)
C3—C2—H2	123.1 (16)	C12—C11—C10	120.1 (2)
C1—C2—H2	116.2 (17)	C12—C11—H9	121.9 (14)
C2—C3—C4	118.70 (18)	C10—C11—H9	117.9 (13)
C2—C3—H3	122.8 (14)	C13—C12—C11	120.5 (2)
C4—C3—H3	118.5 (14)	C13—C12—H10	120.0 (18)
C3—C4—C5	121.41 (18)	C11—C12—H10	119.5 (18)
C3—C4—Cl1	119.49 (15)	C14—C13—C12	119.6 (2)
C5—C4—Cl1	119.05 (15)	C14—C13—H11	121.8 (16)
C6—C5—C4	119.73 (17)	C12—C13—H11	118.6 (16)
C6—C5—H4	122.1 (14)	C13—C14—C15	120.7 (2)
C4—C5—H4	118.2 (14)	C13—C14—H12	122.4 (19)
C5—C6—C1	118.76 (16)	C15—C14—H12	116.9 (19)
C5—C6—C7	120.29 (16)	C14—C15—C10	120.7 (2)
C1—C6—C7	120.92 (18)	C14—C15—H13	121.2 (16)
N1—C7—C6	109.07 (15)	C10—C15—H13	117.6 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1^i	0.850 (19)	2.15 (2)	2.9810 (15)	164 (2)
N3—H8···O1^ii	0.79 (2)	2.06 (2)	2.8322 (17)	167 (2)

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