The conformation of the title compound, C
15H
13ClN
4O, 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(H
2)—C(C
6H
4Cl), 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
CCDC reference: 221717
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-1
H-1,2,4-triazol-5-one
top
Crystal data top
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.126 | All 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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H7···O1i | 0.850 (19) | 2.15 (2) | 2.9810 (15) | 164 (2) |
N3—H8···O1ii | 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. |