4-(3-Bromo­benzyl­idene­amino)-3-(4-chloro­benzyl)-4,5-di­hydro-1H-1,2,4-triazol-5-one

The title compound, C₁₆H₁₂BrClN₄O, contains two benzene rings and a triazole ring which is substituted at the 1,2,4-positions. The crystal structure of (I) is stabilized by N—H...O and π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.076
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as integration
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Cl1     ..       3.52 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1     ..       3.36 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  CG3     ..       2.82 Ang.
PLAT725_ALERT_1_C D-H     Calc     0.93030, Rep     0.95000 Dev...       0.02 Ang.
              C9   -H9      1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

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, 1997) and PARST (Nardelli, 1995).

4-(3-Bromobenzylideneamino)-3-(4-chlorobenzyl)-4,5-dihydro-1H-1,2,4-triazol- 5-one

Crystal data

C16H12BrClN4O	Z = 2
Mr = 391.66	F(000) = 392
Triclinic, P1	Dx = 1.653 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6832 (7) Å	Cell parameters from 13558 reflections
b = 9.4024 (8) Å	θ = 0.0–28.9°
c = 10.7392 (9) Å	µ = 2.79 mm^−1
α = 81.761 (7)°	T = 293 K
β = 73.297 (7)°	Rectangular, colourless
γ = 69.777 (6)°	0.46 × 0.24 × 0.09 mm
V = 787.07 (11) Å^3

Data collection

Stoe IPDS-2 diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: integration	k = −11→11
Tmin = 0.429, Tmax = 0.774	l = −13→13
13505 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 0.0465P] where P = (Fo^2 + 2Fc^2)/3
3090 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.28 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	0.82199 (10)	0.04157 (10)	0.95043 (8)	0.0666 (2)
O1	0.1698 (2)	0.5899 (2)	0.45054 (16)	0.0414 (4)
Br1	0.81727 (4)	0.91640 (3)	0.65863 (3)	0.05440 (12)
C1	0.1446 (3)	0.5704 (3)	0.5690 (2)	0.0329 (5)
N2	0.0329 (2)	0.5130 (2)	0.65465 (19)	0.0361 (4)
H2	−0.0371	0.4816	0.6325	0.043*
N3	0.0399 (2)	0.5088 (2)	0.78231 (19)	0.0383 (5)
C4	0.1577 (3)	0.5651 (3)	0.7755 (2)	0.0341 (5)
N5	0.2278 (2)	0.6057 (2)	0.64852 (18)	0.0323 (4)
N6	0.3532 (2)	0.6728 (2)	0.6184 (2)	0.0338 (4)
C7	0.4146 (3)	0.7065 (3)	0.5007 (2)	0.0362 (5)
H7	0.3732	0.6883	0.4358	0.043*
C8	0.5510 (3)	0.7741 (2)	0.4665 (2)	0.0340 (5)
C9	0.6213 (3)	0.8072 (3)	0.3372 (3)	0.0414 (6)
H9	0.5799	0.7880	0.2727	0.050*
C10	0.7519 (4)	0.8682 (3)	0.3031 (3)	0.0494 (6)
H10	0.7990	0.8886	0.2158	0.059*
C11	0.8126 (3)	0.8988 (3)	0.3976 (3)	0.0486 (7)
H11	0.9008	0.9398	0.3752	0.058*
C12	0.7408 (3)	0.8677 (3)	0.5261 (3)	0.0398 (6)
C13	0.6114 (3)	0.8060 (3)	0.5632 (2)	0.0367 (5)
H13	0.5650	0.7860	0.6507	0.044*
C14	0.2181 (3)	0.5799 (3)	0.8887 (2)	0.0411 (6)
H14A	0.1268	0.5878	0.9674	0.049*
H14B	0.2477	0.6724	0.8760	0.049*
C15	0.3710 (3)	0.4459 (3)	0.9054 (2)	0.0375 (5)
C16	0.5326 (3)	0.4372 (3)	0.8314 (2)	0.0439 (6)
H16	0.5487	0.5162	0.7718	0.053*
C17	0.6713 (3)	0.3122 (3)	0.8447 (3)	0.0480 (7)
H17	0.7797	0.3065	0.7937	0.058*
C18	0.6467 (3)	0.1974 (3)	0.9339 (2)	0.0448 (6)
C19	0.4883 (4)	0.2031 (3)	1.0092 (3)	0.0504 (7)
H19	0.4731	0.1245	1.0695	0.061*
C20	0.3511 (4)	0.3278 (3)	0.9942 (3)	0.0475 (6)
H20	0.2431	0.3323	1.0451	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0592 (4)	0.0752 (5)	0.0626 (5)	−0.0099 (4)	−0.0305 (4)	0.0068 (4)
O1	0.0443 (9)	0.0614 (11)	0.0312 (10)	−0.0315 (9)	−0.0145 (8)	0.0047 (8)
Br1	0.05197 (17)	0.06177 (19)	0.0664 (2)	−0.02921 (13)	−0.02557 (14)	−0.00674 (14)
C1	0.0294 (11)	0.0393 (12)	0.0360 (14)	−0.0145 (10)	−0.0131 (10)	−0.0018 (10)
N2	0.0337 (10)	0.0523 (11)	0.0322 (11)	−0.0248 (9)	−0.0108 (9)	0.0001 (9)
N3	0.0345 (10)	0.0524 (12)	0.0312 (11)	−0.0193 (9)	−0.0070 (9)	−0.0011 (9)
C4	0.0314 (11)	0.0406 (12)	0.0318 (13)	−0.0129 (10)	−0.0078 (10)	−0.0040 (10)
N5	0.0310 (9)	0.0415 (10)	0.0317 (10)	−0.0190 (8)	−0.0104 (8)	−0.0009 (8)
N6	0.0321 (10)	0.0399 (10)	0.0377 (12)	−0.0194 (8)	−0.0128 (9)	−0.0004 (9)
C7	0.0353 (12)	0.0421 (12)	0.0390 (14)	−0.0186 (10)	−0.0132 (11)	−0.0027 (10)
C8	0.0318 (11)	0.0330 (11)	0.0395 (13)	−0.0126 (9)	−0.0100 (10)	−0.0020 (10)
C9	0.0440 (13)	0.0448 (13)	0.0391 (14)	−0.0191 (11)	−0.0102 (12)	−0.0019 (11)
C10	0.0495 (15)	0.0579 (16)	0.0405 (15)	−0.0270 (14)	−0.0012 (13)	0.0024 (12)
C11	0.0419 (14)	0.0506 (15)	0.0581 (18)	−0.0267 (12)	−0.0069 (13)	0.0003 (13)
C12	0.0375 (13)	0.0384 (12)	0.0498 (15)	−0.0161 (11)	−0.0149 (12)	−0.0039 (11)
C13	0.0349 (12)	0.0397 (12)	0.0389 (13)	−0.0164 (10)	−0.0101 (11)	0.0000 (10)
C14	0.0416 (13)	0.0538 (15)	0.0306 (13)	−0.0177 (12)	−0.0067 (11)	−0.0095 (11)
C15	0.0414 (13)	0.0529 (14)	0.0270 (12)	−0.0224 (11)	−0.0112 (10)	−0.0055 (11)
C16	0.0432 (14)	0.0611 (16)	0.0348 (14)	−0.0256 (13)	−0.0150 (12)	0.0070 (12)
C17	0.0361 (13)	0.0742 (18)	0.0371 (14)	−0.0229 (13)	−0.0117 (12)	0.0049 (13)
C18	0.0470 (15)	0.0588 (15)	0.0341 (14)	−0.0176 (13)	−0.0189 (12)	−0.0005 (12)
C19	0.0580 (17)	0.0565 (16)	0.0423 (15)	−0.0272 (14)	−0.0150 (14)	0.0074 (12)
C20	0.0425 (14)	0.0628 (16)	0.0384 (15)	−0.0248 (13)	−0.0021 (12)	−0.0037 (13)

Geometric parameters (Å, º)

Cl1—C18	1.742 (3)	C10—H10	0.9300
O1—C1	1.225 (3)	C11—C12	1.376 (4)
Br1—C12	1.902 (2)	C11—H11	0.9300
C1—N2	1.336 (3)	C12—C13	1.372 (4)
C1—N5	1.402 (3)	C13—H13	0.9300
N2—N3	1.384 (3)	C14—C15	1.516 (3)
N2—H2	0.8600	C14—H14A	0.9700
N3—C4	1.286 (3)	C14—H14B	0.9700
C4—N5	1.382 (3)	C15—C16	1.381 (4)
C4—C14	1.496 (3)	C15—C20	1.381 (4)
N5—N6	1.379 (3)	C16—C17	1.387 (4)
N6—C7	1.264 (3)	C16—H16	0.9300
C7—C8	1.465 (3)	C17—C18	1.369 (4)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.385 (4)	C18—C19	1.368 (4)
C8—C13	1.398 (3)	C19—C20	1.382 (4)
C9—C10	1.378 (4)	C19—H19	0.9300
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.374 (4)
O1—C1—N2	129.9 (2)	C13—C12—Br1	118.1 (2)
O1—C1—N5	127.5 (2)	C11—C12—Br1	119.50 (19)
N2—C1—N5	102.62 (19)	C12—C13—C8	118.5 (2)
C1—N2—N3	113.85 (18)	C12—C13—H13	120.7
C1—N2—H2	123.1	C8—C13—H13	120.7
N3—N2—H2	123.1	C4—C14—C15	111.98 (19)
C4—N3—N2	104.5 (2)	C4—C14—H14A	109.2
N3—C4—N5	111.43 (19)	C15—C14—H14A	109.2
N3—C4—C14	125.0 (2)	C4—C14—H14B	109.2
N5—C4—C14	123.5 (2)	C15—C14—H14B	109.2
N6—N5—C4	121.50 (17)	H14A—C14—H14B	107.9
N6—N5—C1	130.9 (2)	C16—C15—C20	118.3 (2)
C4—N5—C1	107.61 (18)	C16—C15—C14	121.2 (2)
C7—N6—N5	119.19 (18)	C20—C15—C14	120.5 (2)
N6—C7—C8	120.0 (2)	C15—C16—C17	120.9 (3)
N6—C7—H7	120.0	C15—C16—H16	119.6
C8—C7—H7	120.0	C17—C16—H16	119.6
C9—C8—C13	119.4 (2)	C18—C17—C16	119.1 (2)
C9—C8—C7	119.9 (2)	C18—C17—H17	120.4
C13—C8—C7	120.7 (2)	C16—C17—H17	120.4
C10—C9—C8	120.7 (2)	C19—C18—C17	121.3 (3)
C10—C9—H9	119.7	C19—C18—Cl1	119.9 (2)
C8—C9—H9	119.7	C17—C18—Cl1	118.7 (2)
C11—C10—C9	120.2 (3)	C18—C19—C20	118.9 (3)
C11—C10—H10	119.9	C18—C19—H19	120.6
C9—C10—H10	119.9	C20—C19—H19	120.6
C10—C11—C12	118.9 (2)	C15—C20—C19	121.4 (3)
C10—C11—H11	120.6	C15—C20—H20	119.3
C12—C11—H11	120.6	C19—C20—H20	119.3
C13—C12—C11	122.4 (2)
O1—C1—N2—N3	−179.7 (2)	C9—C10—C11—C12	−0.1 (4)
N5—C1—N2—N3	−0.3 (3)	C10—C11—C12—C13	0.5 (4)
C1—N2—N3—C4	0.2 (3)	C10—C11—C12—Br1	−177.6 (2)
N2—N3—C4—N5	−0.1 (3)	C11—C12—C13—C8	0.0 (4)
N2—N3—C4—C14	−177.7 (2)	Br1—C12—C13—C8	178.13 (16)
N3—C4—N5—N6	178.02 (19)	C9—C8—C13—C12	−0.9 (3)
C14—C4—N5—N6	−4.3 (3)	C7—C8—C13—C12	179.2 (2)
N3—C4—N5—C1	−0.1 (3)	N3—C4—C14—C15	94.2 (3)
C14—C4—N5—C1	177.5 (2)	N5—C4—C14—C15	−83.2 (3)
O1—C1—N5—N6	1.7 (4)	C4—C14—C15—C16	81.2 (3)
N2—C1—N5—N6	−177.7 (2)	C4—C14—C15—C20	−97.7 (3)
O1—C1—N5—C4	179.6 (2)	C20—C15—C16—C17	0.8 (3)
N2—C1—N5—C4	0.2 (2)	C14—C15—C16—C17	−178.2 (2)
C4—N5—N6—C7	179.3 (2)	C15—C16—C17—C18	−0.8 (4)
C1—N5—N6—C7	−3.1 (3)	C16—C17—C18—C19	0.4 (4)
N5—N6—C7—C8	−178.35 (19)	C16—C17—C18—Cl1	−179.62 (19)
N6—C7—C8—C9	178.3 (2)	C17—C18—C19—C20	0.1 (4)
N6—C7—C8—C13	−1.8 (3)	Cl1—C18—C19—C20	−179.9 (2)
C13—C8—C9—C10	1.3 (4)	C16—C15—C20—C19	−0.3 (4)
C7—C8—C9—C10	−178.8 (2)	C14—C15—C20—C19	178.7 (2)
C8—C9—C10—C11	−0.8 (4)	C18—C19—C20—C15	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.22	2.906 (3)	130
N2—H2···O1^i	0.86	1.97	2.818 (2)	170
C9—H9···Cg3^ii	0.95	2.82	3.751 (3)	166

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