2-(1H-1,2,3-Benzotriazol-1-yl)-N'-(2-chloro-benzyl-idene)acetohydrazide.

In the title compound, C(15)H(12)ClN(5)O, the mean planes of the benzotriazole and chloro-phenyl fragments form a dihedral angle of 70.8 (1)°. In the crystal, mol-ecules are linked into infinite chains along the a axis by N-H⋯O hydrogen bonds. Weak inter-molecular C-H⋯N hydrogen bonds further link these chains into layers parallel to the ab plane. The crystal studied was a racemic twin.

Related literature

For related structures, see: Shi et al. (2007a ▶,b ▶); Ji & Shi (2008 ▶).

Experimental

Crystal data

C15H12ClN5O

M = 313.75

Monoclinic,

a = 4.6777 (16) Å

b = 11.726 (4) Å

c = 13.328 (5) Å

β = 94.224 (7)°

V = 729.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.979

3851 measured reflections

1902 independent reflections

1370 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.089

S = 1.01

1902 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 544 Flack pairs

Flack parameter: 0.55 (11)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050440/cv5009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050440/cv5009Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12ClN5O	F(000) = 324
Mr = 313.75	Dx = 1.429 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 676 reflections
a = 4.6777 (16) Å	θ = 2.3–18.9°
b = 11.726 (4) Å	µ = 0.27 mm−1
c = 13.328 (5) Å	T = 295 K
β = 94.224 (7)°	Block, colourless
V = 729.0 (4) Å3	0.12 × 0.10 × 0.08 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1902 independent reflections
Radiation source: fine-focus sealed tube	1370 reflections with I > 2σ(I)
graphite	Rint = 0.039
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
Tmin = 0.968, Tmax = 0.979	k = −9→13
3851 measured reflections	l = −15→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0267P)2 + 0.1806P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1902 reflections	Δρmax = 0.16 e Å−3
199 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack (1983), 544 Flack pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.55 (11)

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.

	x	y	z	Uiso*/Ueq
Cl1	1.5224 (3)	0.95422 (11)	0.46424 (9)	0.0660 (4)
O1	0.7318 (6)	0.5815 (3)	0.17718 (18)	0.0473 (8)
N1	0.9309 (7)	0.4707 (3)	0.0172 (2)	0.0377 (8)
N2	0.9247 (9)	0.3561 (3)	0.0325 (3)	0.0523 (10)
N3	0.7297 (9)	0.3113 (3)	−0.0307 (3)	0.0561 (11)
N4	1.1772 (7)	0.6360 (3)	0.2368 (2)	0.0413 (9)
H4	1.3555	0.6412	0.2257	0.050*
N5	1.0786 (8)	0.6779 (3)	0.3252 (2)	0.0391 (9)
C1	0.7313 (9)	0.5002 (4)	−0.0583 (3)	0.0361 (10)
C2	0.6509 (10)	0.6045 (4)	−0.1011 (3)	0.0466 (11)
H2	0.7386	0.6726	−0.0805	0.056*
C3	0.4329 (11)	0.6000 (5)	−0.1759 (3)	0.0619 (14)
H3	0.3692	0.6677	−0.2063	0.074*
C4	0.3028 (11)	0.4976 (6)	−0.2083 (3)	0.0632 (15)
H4A	0.1586	0.4996	−0.2602	0.076*
C5	0.3809 (10)	0.3947 (5)	−0.1661 (3)	0.0585 (14)
H5	0.2931	0.3269	−0.1874	0.070*
C6	0.6035 (10)	0.3978 (4)	−0.0881 (3)	0.0437 (11)
C7	1.1297 (9)	0.5398 (4)	0.0782 (3)	0.0427 (11)
H7A	1.1955	0.6024	0.0383	0.051*
H7B	1.2950	0.4943	0.1011	0.051*
C8	0.9886 (9)	0.5868 (4)	0.1684 (3)	0.0354 (9)
C9	1.2636 (10)	0.7317 (3)	0.3822 (3)	0.0421 (11)
H9	1.4451	0.7469	0.3612	0.050*
C10	1.1839 (9)	0.7691 (4)	0.4815 (3)	0.0406 (10)
C11	1.2939 (9)	0.8682 (4)	0.5275 (3)	0.0446 (11)
C12	1.2219 (10)	0.8998 (4)	0.6219 (3)	0.0564 (13)
H12	1.2975	0.9660	0.6516	0.068*
C13	1.0391 (12)	0.8333 (5)	0.6715 (3)	0.0608 (15)
H13	0.9924	0.8544	0.7355	0.073*
C14	0.9219 (11)	0.7351 (4)	0.6283 (3)	0.0569 (14)
H14	0.7953	0.6908	0.6623	0.068*
C15	0.9967 (10)	0.7035 (4)	0.5332 (3)	0.0481 (12)
H15	0.9198	0.6374	0.5038	0.058*

	U11	U22	U33	U12	U13	U23
Cl1	0.0682 (8)	0.0536 (7)	0.0772 (8)	−0.0105 (7)	0.0128 (7)	−0.0064 (7)
O1	0.0283 (18)	0.071 (2)	0.0436 (17)	−0.0008 (16)	0.0071 (13)	−0.0112 (15)
N1	0.042 (2)	0.032 (2)	0.0409 (19)	−0.0015 (18)	0.0082 (16)	−0.0021 (16)
N2	0.063 (3)	0.038 (2)	0.057 (2)	0.001 (2)	0.010 (2)	0.001 (2)
N3	0.071 (3)	0.038 (2)	0.059 (2)	−0.006 (2)	0.005 (2)	−0.006 (2)
N4	0.033 (2)	0.055 (2)	0.0374 (19)	0.0000 (18)	0.0100 (16)	−0.0138 (17)
N5	0.038 (2)	0.047 (2)	0.033 (2)	0.0031 (18)	0.0092 (17)	−0.0054 (17)
C1	0.035 (3)	0.039 (2)	0.036 (2)	0.000 (2)	0.0133 (19)	−0.0049 (19)
C2	0.051 (3)	0.041 (3)	0.049 (3)	0.003 (2)	0.014 (2)	0.002 (2)
C3	0.058 (4)	0.075 (4)	0.053 (3)	0.014 (3)	0.005 (3)	0.009 (3)
C4	0.051 (3)	0.096 (5)	0.042 (3)	0.007 (3)	0.004 (2)	−0.006 (3)
C5	0.051 (3)	0.079 (4)	0.046 (3)	−0.012 (3)	0.006 (2)	−0.020 (3)
C6	0.053 (3)	0.040 (3)	0.040 (2)	−0.002 (2)	0.014 (2)	−0.009 (2)
C7	0.043 (3)	0.052 (3)	0.035 (2)	−0.006 (2)	0.012 (2)	−0.009 (2)
C8	0.039 (3)	0.037 (2)	0.030 (2)	0.001 (2)	0.0049 (19)	0.0016 (18)
C9	0.041 (3)	0.046 (3)	0.040 (2)	−0.004 (2)	0.006 (2)	−0.007 (2)
C10	0.044 (3)	0.046 (3)	0.032 (2)	0.008 (2)	0.002 (2)	−0.0024 (19)
C11	0.044 (3)	0.046 (3)	0.044 (2)	0.004 (2)	0.002 (2)	−0.003 (2)
C12	0.067 (3)	0.054 (3)	0.048 (3)	0.008 (3)	−0.001 (2)	−0.016 (2)
C13	0.077 (4)	0.071 (4)	0.035 (3)	0.023 (3)	0.010 (3)	−0.007 (3)
C14	0.068 (4)	0.063 (3)	0.042 (3)	0.010 (3)	0.017 (2)	0.002 (2)
C15	0.051 (3)	0.049 (3)	0.044 (3)	0.003 (2)	0.005 (2)	−0.004 (2)

Cl1—C11	1.733 (4)	C4—H4A	0.9300
O1—C8	1.217 (4)	C5—C6	1.416 (6)
N1—N2	1.359 (5)	C5—H5	0.9300
N1—C1	1.366 (5)	C7—C8	1.517 (5)
N1—C7	1.440 (5)	C7—H7A	0.9700
N2—N3	1.306 (5)	C7—H7B	0.9700
N3—C6	1.377 (5)	C9—C10	1.468 (5)
N4—C8	1.350 (5)	C9—H9	0.9300
N4—N5	1.387 (4)	C10—C15	1.386 (6)
N4—H4	0.8600	C10—C11	1.394 (5)
N5—C9	1.275 (5)	C11—C12	1.377 (5)
C1—C6	1.387 (5)	C12—C13	1.364 (6)
C1—C2	1.389 (6)	C12—H12	0.9300
C2—C3	1.374 (6)	C13—C14	1.383 (7)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.399 (7)	C14—C15	1.390 (6)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.370 (7)	C15—H15	0.9300
N2—N1—C1	109.9 (4)	C8—C7—H7A	109.5
N2—N1—C7	119.5 (4)	N1—C7—H7B	109.5
C1—N1—C7	130.6 (3)	C8—C7—H7B	109.5
N3—N2—N1	108.8 (4)	H7A—C7—H7B	108.1
N2—N3—C6	108.2 (3)	O1—C8—N4	123.9 (4)
C8—N4—N5	118.9 (3)	O1—C8—C7	123.2 (4)
C8—N4—H4	120.5	N4—C8—C7	112.9 (4)
N5—N4—H4	120.5	N5—C9—C10	118.5 (4)
C9—N5—N4	115.3 (3)	N5—C9—H9	120.7
N1—C1—C6	104.4 (3)	C10—C9—H9	120.7
N1—C1—C2	132.5 (4)	C15—C10—C11	118.0 (3)
C6—C1—C2	123.1 (4)	C15—C10—C9	119.6 (4)
C3—C2—C1	115.4 (5)	C11—C10—C9	122.4 (4)
C3—C2—H2	122.3	C12—C11—C10	121.3 (4)
C1—C2—H2	122.3	C12—C11—Cl1	119.3 (4)
C2—C3—C4	122.6 (5)	C10—C11—Cl1	119.5 (3)
C2—C3—H3	118.7	C13—C12—C11	119.6 (4)
C4—C3—H3	118.7	C13—C12—H12	120.2
C5—C4—C3	122.2 (5)	C11—C12—H12	120.2
C5—C4—H4A	118.9	C12—C13—C14	121.2 (4)
C3—C4—H4A	118.9	C12—C13—H13	119.4
C4—C5—C6	116.0 (5)	C14—C13—H13	119.4
C4—C5—H5	122.0	C13—C14—C15	118.8 (5)
C6—C5—H5	122.0	C13—C14—H14	120.6
N3—C6—C1	108.7 (4)	C15—C14—H14	120.6
N3—C6—C5	130.6 (4)	C10—C15—C14	121.1 (4)
C1—C6—C5	120.7 (4)	C10—C15—H15	119.4
N1—C7—C8	110.6 (3)	C14—C15—H15	119.4
N1—C7—H7A	109.5
C1—N1—N2—N3	0.4 (4)	N2—N1—C7—C8	−93.6 (4)
C7—N1—N2—N3	179.9 (3)	C1—N1—C7—C8	85.8 (5)
N1—N2—N3—C6	−0.5 (5)	N5—N4—C8—O1	3.6 (6)
C8—N4—N5—C9	−174.3 (4)	N5—N4—C8—C7	−177.1 (3)
N2—N1—C1—C6	−0.1 (4)	N1—C7—C8—O1	−11.3 (6)
C7—N1—C1—C6	−179.6 (4)	N1—C7—C8—N4	169.5 (3)
N2—N1—C1—C2	179.1 (4)	N4—N5—C9—C10	−174.2 (3)
C7—N1—C1—C2	−0.4 (7)	N5—C9—C10—C15	33.0 (6)
N1—C1—C2—C3	−178.9 (4)	N5—C9—C10—C11	−148.1 (4)
C6—C1—C2—C3	0.2 (6)	C15—C10—C11—C12	0.7 (6)
C1—C2—C3—C4	−1.0 (6)	C9—C10—C11—C12	−178.2 (4)
C2—C3—C4—C5	1.2 (8)	C15—C10—C11—Cl1	−178.6 (3)
C3—C4—C5—C6	−0.5 (7)	C9—C10—C11—Cl1	2.6 (6)
N2—N3—C6—C1	0.5 (5)	C10—C11—C12—C13	−0.2 (7)
N2—N3—C6—C5	−179.5 (4)	Cl1—C11—C12—C13	179.1 (4)
N1—C1—C6—N3	−0.2 (4)	C11—C12—C13—C14	−0.7 (7)
C2—C1—C6—N3	−179.5 (4)	C12—C13—C14—C15	0.9 (7)
N1—C1—C6—C5	179.7 (3)	C11—C10—C15—C14	−0.4 (6)
C2—C1—C6—C5	0.4 (6)	C9—C10—C15—C14	178.5 (4)
C4—C5—C6—N3	179.7 (5)	C13—C14—C15—C10	−0.4 (7)
C4—C5—C6—C1	−0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1i	0.86	2.04	2.841 (4)	154.
C7—H7A···N3ii	0.97	2.48	3.320 (6)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1i	0.86	2.04	2.841 (4)	154
C7—H7A⋯N3ii	0.97	2.48	3.320 (6)	145

Symmetry codes: (i) ; (ii) .