N′-(2-Chloro­benzyl­idene)benzo­hydrazide

Fan, C.-G.; Song, M.-Z.

doi:10.1107/S1600536809040331

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2679

https://doi.org/10.1107/S1600536809040331

Open

access

N′-(2-Chlorobenzylidene)benzohydrazide

Chuan-Gang Fan ^a ^* and Ming-Zhi Song ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 23 September 2009; accepted 3 October 2009; online 10 October 2009)

The asymmetric unit of the title compound, C₁₄H₁₁ClN₂O, contains two independent molecules. In one molecule, the two aromatic rings form a dihedral angle of 45.94 (16)°, while in the second molecule this angle is 58.48 (16)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules 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_r = 258.70
Tetragonal, P 4₁
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.093
S = 1.03
4614 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 2105 Friedel pairs
Flack parameter: −0.03 (7)

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) $[y, -x+1, z-{\script{1\over 4}}]$ ; (ii) $[-y+1, x-1, z+{\script{1\over 4}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040331/cv2620Isup2.hkl

checkCIF report

Comment top

Schiff base ligands have received considerable attention during the last decades, mainly because of diversity of their structures and biological properties (Bedia et al., 2006). We report here the crystal structure of the title new Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable with those observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The asymmetric unit of (I) contains two independent molecules- A and B, respectively. In molecule A, two aromatic rings form a dihedral angle of 45.94 (16)°, while in molecule B this angle is 58.48 (16) °.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link molecules into two crystallographically independent sets of chains propagated in direction [001].

Related literature top

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 top

Benzohydrazide (5.0 mmol), ethanol (20 ml) and 2-chlorobenzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing for 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₄H_11ClN₂O: C 65.00, H 4.29, N 10.83%; found: C 65.13, H 4.36, N 10.74%.

Structure description top

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link molecules into two crystallographically independent sets of chains propagated in direction [001].

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).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

N'-(2-Chlorobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O	D_x = 1.298 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0242P)² + 0.8271P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4614 reflections	Δρ_max = 0.21 e Å⁻³
325 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2105 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

Crystal data top

C₁₄H₁₁ClN₂O	Z = 8
M_r = 258.70	Mo Kα radiation
Tetragonal, P4₁	µ = 0.28 mm⁻¹
a = 13.5588 (17) Å	T = 298 K
c = 14.3993 (18) Å	0.45 × 0.42 × 0.38 mm
V = 2647.2 (6) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4614 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2766 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.902	R_int = 0.043
10838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.093	Δρ_max = 0.21 e Å⁻³
S = 1.03	Δρ_min = −0.23 e Å⁻³
4614 reflections	Absolute structure: Flack (1983), 2105 Friedel pairs
325 parameters	Absolute structure parameter: −0.03 (7)
1 restraint

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	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) y, −x+1, z−1/4; (ii) −y+1, x−1, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O
M_r	258.70
Crystal system, space group	Tetragonal, P4₁
Temperature (K)	298
a, c (Å)	13.5588 (17), 14.3993 (18)
V (Å³)	2647.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.45 × 0.42 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.885, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	10838, 4614, 2766
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.093, 1.03
No. of reflections	4614
No. of parameters	325
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23
Absolute structure	Flack (1983), 2105 Friedel pairs
Absolute structure parameter	−0.03 (7)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.01	2.854 (4)	167.7
N3—H3···O2ⁱⁱ	0.86	2.09	2.928 (4)	165.7

Symmetry codes: (i) y, −x+1, z−1/4; (ii) −y+1, x−1, z+1/4.

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYLG200609).

References

Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nie, Y. (2008). Acta Cryst. E64, o471. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar