Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015988/ya6168sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015988/ya6168Isup2.hkl
Contains datablock I

CCDC reference: 221717

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


Yellow Alert 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 top

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 top
Crystal data top
C15H13ClN4OZ = 2
Mr = 300.74F(000) = 312
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1819 (10) ÅCell parameters from 6723 reflections
b = 7.4204 (9) Åθ = 2.7–29.5°
c = 14.3295 (19) ŵ = 0.27 mm1
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) Å3
Data collection top
Stoe IPDS 2
diffractometer
1975 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.044
Plane graphite monochromatorθmax = 24.8°, θmin = 2.9°
Detector resolution: 6.67 pixels mm-1h = 88
φ scansk = 88
2327 measured reflectionsl = 016
2327 independent reflections
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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.126All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2327 reflections(Δ/σ)max < 0.001
242 parametersΔρmax = 0.18 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
Cl10.33854 (10)0.04550 (8)0.63609 (4)0.0819 (3)
O10.07517 (18)0.77037 (17)0.99174 (7)0.0507 (3)
N10.0434 (2)0.49176 (19)0.84166 (9)0.0437 (3)
N20.0262 (2)0.65076 (19)0.84888 (9)0.0432 (3)
N30.0855 (2)0.9054 (2)0.89720 (10)0.0520 (4)
N40.1552 (2)0.8679 (2)0.81252 (10)0.0533 (4)
C10.4266 (3)0.3349 (3)0.88282 (15)0.0624 (5)
C20.4972 (3)0.1803 (4)0.87564 (17)0.0708 (6)
C30.4711 (3)0.0630 (3)0.80058 (16)0.0611 (5)
C40.3699 (3)0.0997 (3)0.73327 (13)0.0526 (4)
C50.2985 (2)0.2542 (2)0.73927 (12)0.0478 (4)
C60.3284 (2)0.3744 (2)0.81405 (12)0.0473 (4)
C70.2599 (3)0.5480 (3)0.81911 (15)0.0574 (5)
C80.0029 (2)0.7783 (2)0.92144 (10)0.0431 (4)
C90.1181 (2)0.7124 (2)0.78393 (11)0.0454 (4)
C100.1649 (2)0.6265 (3)0.69367 (11)0.0491 (4)
C110.1725 (3)0.4417 (3)0.67111 (13)0.0554 (5)
C120.2206 (3)0.3708 (4)0.58469 (15)0.0674 (6)
C130.2632 (3)0.4811 (4)0.52129 (15)0.0755 (7)
C140.2575 (4)0.6624 (5)0.54343 (16)0.0819 (7)
C150.2090 (3)0.7354 (4)0.62860 (14)0.0682 (6)
H10.441 (4)0.407 (4)0.932 (2)0.092 (8)*
H20.569 (4)0.165 (4)0.9248 (18)0.088 (7)*
H30.527 (3)0.051 (4)0.7914 (16)0.078 (6)*
H40.229 (3)0.271 (3)0.6936 (15)0.060 (5)*
H50.299 (3)0.619 (3)0.7554 (16)0.075 (6)*
H60.324 (4)0.639 (4)0.8696 (18)0.083 (7)*
H70.004 (3)0.435 (3)0.8948 (14)0.046 (5)*
H80.094 (3)0.999 (3)0.9231 (15)0.055 (6)*
H90.152 (3)0.368 (3)0.7162 (15)0.058 (5)*
H100.230 (4)0.247 (5)0.571 (2)0.091 (8)*
H110.301 (4)0.424 (4)0.459 (2)0.094 (8)*
H120.287 (5)0.752 (5)0.497 (2)0.120 (10)*
H130.190 (3)0.855 (4)0.6403 (17)0.069 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1031 (5)0.0573 (4)0.0828 (4)0.0261 (3)0.0065 (3)0.0238 (3)
O10.0770 (8)0.0471 (7)0.0388 (6)0.0327 (6)0.0138 (5)0.0060 (5)
N10.0565 (8)0.0365 (7)0.0433 (7)0.0224 (6)0.0072 (6)0.0033 (6)
N20.0560 (7)0.0410 (8)0.0393 (6)0.0248 (6)0.0077 (5)0.0053 (5)
N30.0749 (9)0.0491 (9)0.0458 (7)0.0381 (8)0.0141 (6)0.0121 (6)
N40.0661 (8)0.0589 (9)0.0489 (7)0.0367 (7)0.0166 (6)0.0092 (6)
C10.0682 (11)0.0681 (14)0.0553 (10)0.0242 (10)0.0160 (8)0.0086 (9)
C20.0677 (11)0.0781 (15)0.0768 (13)0.0296 (11)0.0224 (10)0.0146 (11)
C30.0566 (10)0.0503 (11)0.0826 (13)0.0271 (9)0.0053 (9)0.0080 (10)
C40.0517 (9)0.0414 (9)0.0629 (10)0.0163 (8)0.0012 (7)0.0033 (8)
C50.0505 (8)0.0469 (10)0.0507 (9)0.0209 (7)0.0092 (7)0.0002 (7)
C60.0470 (8)0.0436 (9)0.0534 (9)0.0189 (7)0.0033 (6)0.0024 (7)
C70.0567 (10)0.0425 (10)0.0744 (12)0.0220 (8)0.0006 (9)0.0040 (9)
C80.0559 (8)0.0427 (9)0.0363 (7)0.0248 (7)0.0043 (6)0.0026 (6)
C90.0473 (8)0.0509 (10)0.0441 (8)0.0238 (7)0.0073 (6)0.0017 (7)
C100.0424 (8)0.0620 (11)0.0456 (8)0.0194 (8)0.0073 (6)0.0060 (7)
C110.0521 (9)0.0594 (12)0.0512 (9)0.0118 (8)0.0078 (7)0.0078 (8)
C120.0570 (10)0.0729 (15)0.0644 (11)0.0089 (10)0.0092 (8)0.0231 (10)
C130.0646 (11)0.108 (2)0.0539 (11)0.0225 (12)0.0197 (9)0.0240 (12)
C140.0918 (15)0.111 (2)0.0571 (11)0.0431 (15)0.0308 (10)0.0104 (12)
C150.0815 (13)0.0804 (16)0.0582 (11)0.0408 (12)0.0252 (9)0.0088 (10)
Geometric parameters (Å, º) top
Cl1—C41.736 (2)C4—C51.382 (2)
O1—C81.2381 (19)C5—C61.375 (3)
N1—N21.4054 (17)C5—H40.91 (2)
N1—C71.472 (2)C6—C71.504 (2)
N1—H70.850 (19)C7—H51.02 (2)
N2—C81.380 (2)C7—H61.04 (3)
N2—C91.381 (2)C9—C101.467 (2)
N3—C81.332 (2)C10—C151.383 (3)
N3—N41.374 (2)C10—C111.386 (3)
N3—H80.79 (2)C11—C121.385 (3)
N4—C91.299 (2)C11—H90.92 (2)
C1—C21.379 (3)C12—C131.368 (4)
C1—C61.382 (3)C12—H100.92 (3)
C1—H10.87 (3)C13—C141.363 (4)
C2—C31.364 (3)C13—H111.02 (3)
C2—H20.97 (3)C14—C151.373 (3)
C3—C41.373 (3)C14—H121.04 (3)
C3—H31.03 (2)C15—H130.87 (3)
N2—N1—C7110.79 (13)N1—C7—H5107.8 (12)
N2—N1—H7106.3 (12)C6—C7—H5110.8 (13)
C7—N1—H7111.0 (12)N1—C7—H6111.2 (13)
C8—N2—C9108.47 (12)C6—C7—H6110.0 (14)
C8—N2—N1124.60 (12)H5—C7—H6108.0 (19)
C9—N2—N1126.84 (13)O1—C8—N3129.87 (16)
C8—N3—N4113.12 (15)O1—C8—N2126.78 (13)
C8—N3—H8129.1 (15)N3—C8—N2103.34 (13)
N4—N3—H8117.7 (15)N4—C9—N2109.72 (14)
C9—N4—N3105.32 (13)N4—C9—C10122.54 (14)
C2—C1—C6120.7 (2)N2—C9—C10127.70 (14)
C2—C1—H1119.7 (19)C15—C10—C11118.40 (18)
C6—C1—H1119.5 (19)C15—C10—C9117.78 (18)
C3—C2—C1120.63 (19)C11—C10—C9123.80 (16)
C3—C2—H2123.1 (16)C12—C11—C10120.1 (2)
C1—C2—H2116.2 (17)C12—C11—H9121.9 (14)
C2—C3—C4118.70 (18)C10—C11—H9117.9 (13)
C2—C3—H3122.8 (14)C13—C12—C11120.5 (2)
C4—C3—H3118.5 (14)C13—C12—H10120.0 (18)
C3—C4—C5121.41 (18)C11—C12—H10119.5 (18)
C3—C4—Cl1119.49 (15)C14—C13—C12119.6 (2)
C5—C4—Cl1119.05 (15)C14—C13—H11121.8 (16)
C6—C5—C4119.73 (17)C12—C13—H11118.6 (16)
C6—C5—H4122.1 (14)C13—C14—C15120.7 (2)
C4—C5—H4118.2 (14)C13—C14—H12122.4 (19)
C5—C6—C1118.76 (16)C15—C14—H12116.9 (19)
C5—C6—C7120.29 (16)C14—C15—C10120.7 (2)
C1—C6—C7120.92 (18)C14—C15—H13121.2 (16)
N1—C7—C6109.07 (15)C10—C15—H13117.6 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H7···O1i0.850 (19)2.15 (2)2.9810 (15)164 (2)
N3—H8···O1ii0.79 (2)2.06 (2)2.8322 (17)167 (2)
Symmetry codes: (i) x, y1, z+2; (ii) x, y2, z+2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds