N'-(2-Chloro-benzyl-idene)benzo-hydrazide.

The asymmetric unit of the title compound, C(14)H(11)ClN(2)O, contains two independent mol-ecules. In one mol-ecule, the two aromatic rings form a dihedral angle of 45.94 (16)°, while in the second mol-ecule this angle is 58.48 (16)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into two crystallographically independent sets of chains propagating along [001].

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Nie (2008 ▶).

Experimental

Crystal data

C14H11ClN2O

M = 258.70

Tetragonal,

a = 13.5588 (17) Å

c = 14.3993 (18) Å

V = 2647.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.45 × 0.42 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.902

10838 measured reflections

4614 independent reflections

2766 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.093

S = 1.03

4614 reflections

325 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 2105 Friedel pairs

Flack parameter: −0.03 (7)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040331/cv2620sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040331/cv2620Isup2.hkl

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

C14H11ClN2O	Dx = 1.298 Mg m−3
Mr = 258.70	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41	Cell parameters from 2946 reflections
a = 13.5588 (17) Å	θ = 2.6–25.3°
c = 14.3993 (18) Å	µ = 0.28 mm−1
V = 2647.2 (6) Å3	T = 298 K
Z = 8	Needle, colourless
F(000) = 1072	0.45 × 0.42 × 0.38 mm

Bruker SMART APEX CCD area-detector diffractometer	4614 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→16
Tmin = 0.885, Tmax = 0.902	k = −6→16
10838 measured reflections	l = −16→17

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0242P)2 + 0.8271P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4614 reflections	Δρmax = 0.21 e Å−3
325 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 2105 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (7)

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	0.75607 (8)	0.65234 (7)	0.24623 (8)	0.0633 (3)
Cl2	0.88744 (9)	−0.28276 (9)	0.02864 (13)	0.1075 (6)
N1	0.4131 (2)	0.5479 (2)	0.3296 (2)	0.0408 (8)
H1	0.4139	0.5829	0.2798	0.049*
N2	0.4972 (2)	0.53797 (19)	0.3835 (2)	0.0405 (8)
N3	0.9519 (2)	0.0803 (2)	0.0223 (2)	0.0495 (9)
H3	0.9112	0.0700	0.0670	0.059*
N4	1.0075 (2)	0.0039 (2)	−0.0142 (2)	0.0494 (8)
O1	0.32675 (18)	0.44465 (18)	0.42320 (19)	0.0536 (7)
O2	1.00890 (19)	0.18599 (17)	−0.0864 (2)	0.0543 (7)
C1	0.3299 (3)	0.5015 (3)	0.3567 (3)	0.0402 (9)
C2	0.2392 (2)	0.5252 (3)	0.3029 (3)	0.0418 (9)
C3	0.1631 (3)	0.4574 (3)	0.3042 (3)	0.0642 (13)
H3A	0.1708	0.3979	0.3354	0.077*
C4	0.0752 (3)	0.4782 (4)	0.2591 (3)	0.0827 (15)
H4	0.0250	0.4314	0.2577	0.099*
C5	0.0623 (3)	0.5671 (4)	0.2167 (4)	0.0843 (16)
H5	0.0022	0.5819	0.1888	0.101*
C6	0.1368 (3)	0.6345 (4)	0.2148 (3)	0.0742 (14)
H6	0.1278	0.6944	0.1845	0.089*
C7	0.2262 (3)	0.6142 (3)	0.2578 (3)	0.0542 (10)
H7	0.2770	0.6602	0.2564	0.065*
C8	0.5738 (3)	0.5796 (3)	0.3501 (3)	0.0425 (9)
H8	0.5704	0.6102	0.2924	0.051*
C9	0.6667 (2)	0.5797 (2)	0.4014 (3)	0.0399 (9)
C10	0.7535 (3)	0.6149 (2)	0.3604 (3)	0.0411 (9)
C11	0.8398 (3)	0.6218 (3)	0.4122 (3)	0.0536 (11)
H11	0.8971	0.6458	0.3848	0.064*
C12	0.8404 (3)	0.5931 (3)	0.5037 (4)	0.0599 (11)
H12	0.8980	0.5986	0.5383	0.072*
C13	0.7562 (3)	0.5561 (3)	0.5445 (3)	0.0551 (11)
H13	0.7571	0.5351	0.6060	0.066*
C14	0.6715 (3)	0.5508 (3)	0.4937 (3)	0.0485 (10)
H14	0.6147	0.5268	0.5220	0.058*
C15	0.9631 (2)	0.1712 (3)	−0.0140 (3)	0.0429 (9)
C16	0.9164 (2)	0.2533 (2)	0.0384 (3)	0.0382 (9)
C17	0.8908 (3)	0.2462 (3)	0.1306 (3)	0.0509 (11)
H17	0.9009	0.1873	0.1623	0.061*
C18	0.8502 (3)	0.3259 (3)	0.1762 (3)	0.0638 (13)
H18	0.8329	0.3207	0.2385	0.077*
C19	0.8352 (3)	0.4131 (3)	0.1296 (4)	0.0666 (14)
H19	0.8080	0.4668	0.1605	0.080*
C20	0.8601 (3)	0.4213 (3)	0.0382 (4)	0.0624 (13)
H20	0.8499	0.4805	0.0070	0.075*
C21	0.9006 (2)	0.3416 (3)	−0.0083 (3)	0.0481 (10)
H21	0.9172	0.3471	−0.0708	0.058*
C22	0.9846 (3)	−0.0815 (3)	0.0139 (3)	0.0517 (11)
H22	0.9300	−0.0898	0.0521	0.062*
C23	1.0434 (3)	−0.1671 (3)	−0.0132 (3)	0.0534 (11)
C24	1.0065 (3)	−0.2622 (3)	−0.0086 (3)	0.0586 (11)
C25	1.0630 (4)	−0.3424 (3)	−0.0335 (3)	0.0702 (14)
H25	1.0364	−0.4055	−0.0300	0.084*
C26	1.1573 (4)	−0.3296 (3)	−0.0630 (3)	0.0798 (15)
H26	1.1956	−0.3839	−0.0791	0.096*
C27	1.1960 (4)	−0.2360 (4)	−0.0689 (4)	0.0951 (19)
H27	1.2604	−0.2270	−0.0896	0.114*
C28	1.1396 (3)	−0.1556 (3)	−0.0444 (4)	0.0887 (18)
H28	1.1664	−0.0926	−0.0487	0.106*

	U11	U22	U33	U12	U13	U23
Cl1	0.0684 (7)	0.0568 (6)	0.0646 (7)	−0.0023 (5)	0.0190 (6)	0.0062 (6)
Cl2	0.0785 (9)	0.0592 (8)	0.1849 (18)	−0.0126 (7)	0.0274 (10)	0.0013 (9)
N1	0.0326 (18)	0.049 (2)	0.041 (2)	−0.0026 (15)	−0.0042 (15)	0.0040 (15)
N2	0.0316 (17)	0.0436 (18)	0.046 (2)	−0.0003 (15)	−0.0021 (16)	−0.0020 (15)
N3	0.053 (2)	0.0354 (18)	0.060 (2)	0.0021 (15)	0.0208 (17)	−0.0004 (16)
N4	0.0535 (19)	0.0383 (18)	0.057 (2)	0.0034 (16)	0.0091 (17)	−0.0023 (17)
O1	0.0470 (16)	0.0590 (18)	0.055 (2)	−0.0098 (13)	−0.0089 (13)	0.0145 (15)
O2	0.0614 (18)	0.0442 (16)	0.0573 (19)	−0.0025 (14)	0.0186 (16)	0.0003 (14)
C1	0.042 (2)	0.038 (2)	0.040 (2)	−0.0029 (18)	−0.0036 (19)	0.0017 (19)
C2	0.033 (2)	0.052 (2)	0.040 (2)	−0.0049 (19)	−0.0028 (18)	−0.0031 (19)
C3	0.049 (3)	0.079 (3)	0.065 (3)	−0.018 (2)	−0.010 (2)	0.011 (3)
C4	0.049 (3)	0.125 (4)	0.074 (4)	−0.029 (3)	−0.015 (3)	0.012 (3)
C5	0.039 (3)	0.140 (5)	0.073 (4)	0.008 (3)	−0.010 (2)	0.011 (4)
C6	0.062 (3)	0.089 (4)	0.071 (4)	0.017 (3)	−0.009 (3)	0.013 (3)
C7	0.042 (2)	0.066 (3)	0.054 (3)	0.003 (2)	−0.002 (2)	0.003 (2)
C8	0.043 (2)	0.043 (2)	0.041 (2)	0.0016 (19)	0.0004 (19)	0.0003 (19)
C9	0.033 (2)	0.034 (2)	0.052 (3)	−0.0017 (17)	0.0039 (19)	−0.0032 (19)
C10	0.047 (2)	0.030 (2)	0.047 (3)	−0.0011 (18)	0.010 (2)	−0.0036 (18)
C11	0.040 (2)	0.041 (2)	0.080 (4)	−0.0033 (18)	0.006 (2)	−0.006 (2)
C12	0.045 (3)	0.059 (3)	0.076 (4)	−0.002 (2)	−0.009 (3)	−0.006 (3)
C13	0.044 (3)	0.067 (3)	0.054 (3)	0.000 (2)	−0.004 (2)	0.004 (2)
C14	0.038 (2)	0.053 (2)	0.054 (3)	−0.0016 (18)	−0.001 (2)	0.005 (2)
C15	0.035 (2)	0.038 (2)	0.056 (3)	−0.0038 (17)	0.002 (2)	−0.002 (2)
C16	0.032 (2)	0.033 (2)	0.050 (3)	−0.0007 (16)	0.0021 (17)	−0.0049 (19)
C17	0.047 (2)	0.048 (2)	0.058 (3)	0.003 (2)	−0.001 (2)	−0.003 (2)
C18	0.066 (3)	0.063 (3)	0.062 (3)	0.000 (3)	0.008 (2)	−0.022 (3)
C19	0.054 (3)	0.056 (3)	0.090 (4)	0.005 (2)	−0.002 (3)	−0.027 (3)
C20	0.053 (3)	0.036 (2)	0.098 (4)	0.003 (2)	−0.016 (3)	−0.001 (3)
C21	0.043 (2)	0.038 (2)	0.063 (3)	−0.0031 (18)	−0.001 (2)	−0.001 (2)
C22	0.054 (2)	0.039 (2)	0.062 (3)	0.001 (2)	0.017 (2)	−0.001 (2)
C23	0.057 (3)	0.044 (3)	0.059 (3)	0.010 (2)	0.012 (2)	0.006 (2)
C24	0.068 (3)	0.041 (2)	0.067 (3)	0.003 (2)	0.005 (3)	−0.001 (2)
C25	0.091 (4)	0.048 (3)	0.072 (4)	0.015 (3)	0.003 (3)	−0.002 (2)
C26	0.100 (4)	0.059 (3)	0.081 (4)	0.034 (3)	0.017 (3)	0.006 (3)
C27	0.086 (4)	0.070 (4)	0.130 (5)	0.017 (3)	0.047 (4)	0.015 (3)
C28	0.076 (3)	0.055 (3)	0.136 (5)	0.006 (3)	0.043 (3)	0.012 (3)

Cl1—C10	1.721 (4)	C11—H11	0.9300
Cl2—C24	1.724 (4)	C12—C13	1.379 (5)
N1—C1	1.350 (4)	C12—H12	0.9300
N1—N2	1.386 (4)	C13—C14	1.364 (5)
N1—H1	0.8600	C13—H13	0.9300
N2—C8	1.277 (4)	C14—H14	0.9300
N3—C15	1.347 (4)	C15—C16	1.487 (5)
N3—N4	1.385 (4)	C16—C17	1.375 (5)
N3—H3	0.8600	C16—C21	1.389 (5)
N4—C22	1.264 (4)	C17—C18	1.379 (5)
O1—C1	1.230 (4)	C17—H17	0.9300
O2—C15	1.230 (4)	C18—C19	1.375 (6)
C1—C2	1.488 (5)	C18—H18	0.9300
C2—C3	1.382 (5)	C19—C20	1.364 (6)
C2—C7	1.381 (5)	C19—H19	0.9300
C3—C4	1.387 (5)	C20—C21	1.385 (5)
C3—H3A	0.9300	C20—H20	0.9300
C4—C5	1.362 (6)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.461 (5)
C5—C6	1.362 (6)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.385 (5)
C6—C7	1.389 (5)	C23—C28	1.388 (5)
C6—H6	0.9300	C24—C25	1.376 (5)
C7—H7	0.9300	C25—C26	1.359 (6)
C8—C9	1.459 (5)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.376 (6)
C9—C14	1.388 (5)	C26—H26	0.9300
C9—C10	1.400 (5)	C27—C28	1.378 (6)
C10—C11	1.390 (5)	C27—H27	0.9300
C11—C12	1.374 (6)	C28—H28	0.9300
C1—N1—N2	118.7 (3)	C12—C13—H13	120.4
C1—N1—H1	120.6	C13—C14—C9	122.6 (4)
N2—N1—H1	120.6	C13—C14—H14	118.7
C8—N2—N1	114.5 (3)	C9—C14—H14	118.7
C15—N3—N4	118.4 (3)	O2—C15—N3	122.4 (3)
C15—N3—H3	120.8	O2—C15—C16	121.5 (3)
N4—N3—H3	120.8	N3—C15—C16	116.1 (4)
C22—N4—N3	115.5 (3)	C17—C16—C21	119.3 (4)
O1—C1—N1	123.1 (3)	C17—C16—C15	123.0 (3)
O1—C1—C2	120.8 (3)	C21—C16—C15	117.7 (4)
N1—C1—C2	116.1 (3)	C16—C17—C18	120.3 (4)
C3—C2—C7	119.4 (3)	C16—C17—H17	119.8
C3—C2—C1	117.8 (3)	C18—C17—H17	119.8
C7—C2—C1	122.6 (3)	C19—C18—C17	120.0 (5)
C2—C3—C4	120.0 (4)	C19—C18—H18	120.0
C2—C3—H3A	120.0	C17—C18—H18	120.0
C4—C3—H3A	120.0	C20—C19—C18	120.3 (4)
C5—C4—C3	120.0 (4)	C20—C19—H19	119.9
C5—C4—H4	120.0	C18—C19—H19	119.9
C3—C4—H4	120.0	C19—C20—C21	120.1 (4)
C6—C5—C4	120.5 (4)	C19—C20—H20	120.0
C6—C5—H5	119.8	C21—C20—H20	120.0
C4—C5—H5	119.8	C20—C21—C16	120.0 (4)
C5—C6—C7	120.3 (5)	C20—C21—H21	120.0
C5—C6—H6	119.8	C16—C21—H21	120.0
C7—C6—H6	119.8	N4—C22—C23	120.5 (4)
C2—C7—C6	119.6 (4)	N4—C22—H22	119.7
C2—C7—H7	120.2	C23—C22—H22	119.7
C6—C7—H7	120.2	C24—C23—C28	117.4 (4)
N2—C8—C9	120.8 (3)	C24—C23—C22	122.0 (4)
N2—C8—H8	119.6	C28—C23—C22	120.6 (4)
C9—C8—H8	119.6	C25—C24—C23	121.5 (4)
C14—C9—C10	117.4 (3)	C25—C24—Cl2	118.3 (3)
C14—C9—C8	121.7 (3)	C23—C24—Cl2	120.2 (3)
C10—C9—C8	120.8 (4)	C26—C25—C24	120.3 (4)
C11—C10—C9	120.3 (4)	C26—C25—H25	119.9
C11—C10—Cl1	118.4 (3)	C24—C25—H25	119.9
C9—C10—Cl1	121.3 (3)	C25—C26—C27	119.7 (4)
C12—C11—C10	120.0 (4)	C25—C26—H26	120.1
C12—C11—H11	120.0	C27—C26—H26	120.1
C10—C11—H11	120.0	C26—C27—C28	120.2 (5)
C11—C12—C13	120.5 (4)	C26—C27—H27	119.9
C11—C12—H12	119.8	C28—C27—H27	119.9
C13—C12—H12	119.8	C27—C28—C23	121.0 (4)
C14—C13—C12	119.2 (4)	C27—C28—H28	119.5
C14—C13—H13	120.4	C23—C28—H28	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.01	2.854 (4)	168
N3—H3···O2ii	0.86	2.09	2.928 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.01	2.854 (4)	168
N3—H3⋯O2ii	0.86	2.09	2.928 (4)	166

Symmetry codes: (i) ; (ii) .