(Z)-Ethyl 2-chloro-2-[2-(4-methyl-phen-yl)hydrazinyl-idene]acetate.

The mol-ecule of the title compound, C11H13ClN2O2, is approximately planar (r.m.s. deviation = 0.099 Å for non-H atoms) and adopts a Z conformation about the C=N double bond. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds to the same O-atom acceptor, forming zigzag chains propagating along [010]. These inter-actions give rise to R2(1)(6) loops.

Related literature

For related structures, see: Asiri et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C11H13ClN2O2

M = 240.68

Monoclinic,

a = 4.6152 (1) Å

b = 9.9444 (1) Å

c = 26.3152 (3) Å

β = 90.692 (1)°

V = 1207.66 (3) Å3

Z = 4

Cu Kα radiation

μ = 2.71 mm−1

T = 296 K

0.41 × 0.14 × 0.13 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.692, T max = 1.000

9526 measured reflections

2436 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.06

2436 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046521/hb6984sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046521/hb6984Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046521/hb6984Isup3.cml

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

C11H13ClN2O2	F(000) = 504
Mr = 240.68	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 6552 reflections
a = 4.6152 (1) Å	θ = 4.4–75.9°
b = 9.9444 (1) Å	µ = 2.71 mm−1
c = 26.3152 (3) Å	T = 296 K
β = 90.692 (1)°	Needle, yellow
V = 1207.66 (3) Å3	0.41 × 0.14 × 0.13 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer	2436 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2224 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.019
ω scans	θmax = 76.1°, θmin = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −4→5
Tmin = 0.692, Tmax = 1.000	k = −12→12
9526 measured reflections	l = −32→33

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2618P] where P = (Fo2 + 2Fc2)/3
2436 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.43464 (11)	0.05667 (5)	0.234472 (17)	0.07524 (19)
O1	0.1041 (3)	0.28559 (14)	0.27188 (5)	0.0730 (4)
O2	0.2685 (3)	0.27966 (12)	0.35220 (4)	0.0641 (3)
N1	0.8092 (3)	−0.02052 (14)	0.31951 (5)	0.0541 (3)
N2	0.6346 (3)	0.08135 (12)	0.32924 (5)	0.0508 (3)
C1	0.9873 (3)	−0.07483 (15)	0.35803 (6)	0.0491 (3)
C2	1.0086 (4)	−0.01791 (17)	0.40583 (6)	0.0579 (4)
H2	0.9035	0.0590	0.4136	0.070*
C3	1.1886 (4)	−0.07686 (18)	0.44203 (6)	0.0621 (4)
H3	1.2034	−0.0379	0.4741	0.074*
C4	1.3468 (3)	−0.19164 (17)	0.43198 (6)	0.0574 (4)
C5	1.3267 (4)	−0.24428 (17)	0.38355 (7)	0.0626 (4)
H5	1.4356	−0.3199	0.3755	0.075*
C6	1.1496 (4)	−0.18777 (17)	0.34674 (6)	0.0592 (4)
H6	1.1393	−0.2255	0.3144	0.071*
C7	0.4608 (3)	0.12591 (16)	0.29498 (6)	0.0518 (3)
C8	0.2603 (3)	0.23844 (16)	0.30433 (6)	0.0546 (4)
C9	0.0576 (5)	0.3840 (2)	0.36460 (8)	0.0774 (5)
H9A	0.1042	0.4668	0.3470	0.093*
H9B	−0.1354	0.3560	0.3541	0.093*
C10	0.0685 (7)	0.4052 (3)	0.41932 (10)	0.1069 (9)
H10A	0.0065	0.3250	0.4363	0.160*
H10B	−0.0572	0.4783	0.4281	0.160*
H10C	0.2634	0.4263	0.4297	0.160*
C11	1.5322 (5)	−0.2579 (2)	0.47260 (8)	0.0768 (5)
H11A	1.4576	−0.3460	0.4797	0.115*
H11B	1.5289	−0.2045	0.5030	0.115*
H11C	1.7278	−0.2653	0.4609	0.115*
H1	0.799 (5)	−0.063 (2)	0.2915 (10)	0.092*

	U11	U22	U33	U12	U13	U23
Cl1	0.0816 (3)	0.0890 (3)	0.0549 (3)	0.0032 (2)	−0.0103 (2)	−0.0051 (2)
O1	0.0795 (8)	0.0712 (8)	0.0680 (7)	0.0077 (6)	−0.0172 (6)	0.0174 (6)
O2	0.0687 (7)	0.0615 (7)	0.0618 (7)	0.0123 (5)	−0.0083 (5)	0.0025 (5)
N1	0.0542 (7)	0.0577 (7)	0.0502 (7)	0.0023 (6)	−0.0021 (6)	−0.0015 (6)
N2	0.0478 (7)	0.0507 (7)	0.0539 (7)	−0.0047 (5)	−0.0002 (5)	0.0055 (5)
C1	0.0459 (7)	0.0495 (7)	0.0520 (8)	−0.0049 (6)	0.0007 (6)	0.0022 (6)
C2	0.0621 (9)	0.0567 (8)	0.0549 (8)	0.0072 (7)	0.0012 (7)	−0.0032 (7)
C3	0.0664 (10)	0.0685 (10)	0.0513 (9)	0.0011 (8)	−0.0026 (7)	−0.0048 (7)
C4	0.0508 (8)	0.0597 (9)	0.0615 (9)	−0.0048 (7)	−0.0038 (7)	0.0064 (7)
C5	0.0611 (10)	0.0557 (9)	0.0709 (10)	0.0073 (7)	−0.0042 (8)	−0.0039 (7)
C6	0.0639 (10)	0.0575 (9)	0.0561 (9)	0.0035 (7)	−0.0023 (7)	−0.0083 (7)
C7	0.0502 (8)	0.0552 (8)	0.0499 (8)	−0.0079 (6)	−0.0021 (6)	0.0064 (6)
C8	0.0549 (8)	0.0529 (8)	0.0557 (8)	−0.0078 (6)	−0.0039 (7)	0.0122 (6)
C9	0.0837 (13)	0.0655 (11)	0.0826 (13)	0.0187 (10)	−0.0084 (10)	0.0009 (9)
C10	0.137 (2)	0.0947 (17)	0.0889 (17)	0.0374 (16)	0.0124 (15)	−0.0014 (13)
C11	0.0738 (12)	0.0788 (12)	0.0773 (12)	0.0022 (9)	−0.0163 (10)	0.0121 (10)

Cl1—C7	1.7377 (16)	C4—C11	1.512 (2)
O1—C8	1.2056 (19)	C5—C6	1.380 (2)
O2—C8	1.325 (2)	C5—H5	0.9300
O2—C9	1.462 (2)	C6—H6	0.9300
N1—N2	1.3215 (19)	C7—C8	1.475 (2)
N1—C1	1.405 (2)	C9—C10	1.456 (3)
N1—H1	0.85 (2)	C9—H9A	0.9700
N2—C7	1.2788 (19)	C9—H9B	0.9700
C1—C2	1.382 (2)	C10—H10A	0.9600
C1—C6	1.384 (2)	C10—H10B	0.9600
C2—C3	1.386 (2)	C10—H10C	0.9600
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.382 (2)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.380 (2)
C8—O2—C9	114.85 (13)	N2—C7—Cl1	123.01 (13)
N2—N1—C1	120.49 (13)	C8—C7—Cl1	114.63 (11)
N2—N1—H1	121.5 (16)	O1—C8—O2	124.26 (16)
C1—N1—H1	117.4 (16)	O1—C8—C7	123.24 (16)
C7—N2—N1	120.52 (14)	O2—C8—C7	112.49 (13)
C2—C1—C6	119.67 (15)	C10—C9—O2	107.95 (17)
C2—C1—N1	122.27 (14)	C10—C9—H9A	110.1
C6—C1—N1	118.05 (14)	O2—C9—H9A	110.1
C1—C2—C3	119.20 (15)	C10—C9—H9B	110.1
C1—C2—H2	120.4	O2—C9—H9B	110.1
C3—C2—H2	120.4	H9A—C9—H9B	108.4
C4—C3—C2	122.08 (16)	C9—C10—H10A	109.5
C4—C3—H3	119.0	C9—C10—H10B	109.5
C2—C3—H3	119.0	H10A—C10—H10B	109.5
C5—C4—C3	117.41 (15)	C9—C10—H10C	109.5
C5—C4—C11	121.23 (17)	H10A—C10—H10C	109.5
C3—C4—C11	121.35 (17)	H10B—C10—H10C	109.5
C6—C5—C4	121.77 (16)	C4—C11—H11A	109.5
C6—C5—H5	119.1	C4—C11—H11B	109.5
C4—C5—H5	119.1	H11A—C11—H11B	109.5
C5—C6—C1	119.83 (15)	C4—C11—H11C	109.5
C5—C6—H6	120.1	H11A—C11—H11C	109.5
C1—C6—H6	120.1	H11B—C11—H11C	109.5
N2—C7—C8	122.34 (14)
C1—N1—N2—C7	−176.05 (13)	C2—C1—C6—C5	1.3 (2)
N2—N1—C1—C2	−6.0 (2)	N1—C1—C6—C5	−179.88 (15)
N2—N1—C1—C6	175.21 (14)	N1—N2—C7—C8	179.40 (13)
C6—C1—C2—C3	−1.3 (2)	N1—N2—C7—Cl1	1.1 (2)
N1—C1—C2—C3	179.99 (15)	C9—O2—C8—O1	3.6 (2)
C1—C2—C3—C4	−0.4 (3)	C9—O2—C8—C7	−175.40 (14)
C2—C3—C4—C5	2.0 (3)	N2—C7—C8—O1	176.63 (15)
C2—C3—C4—C11	−177.38 (17)	Cl1—C7—C8—O1	−4.9 (2)
C3—C4—C5—C6	−1.9 (3)	N2—C7—C8—O2	−4.4 (2)
C11—C4—C5—C6	177.44 (17)	Cl1—C7—C8—O2	174.06 (11)
C4—C5—C6—C1	0.3 (3)	C8—O2—C9—C10	172.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.52	3.331 (2)	145
N1—H1···O1i	0.85 (2)	2.30 (2)	3.1120 (18)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.52	3.331 (2)	145
N1—H1⋯O1i	0.85 (2)	2.30 (2)	3.1120 (18)	161 (2)

Symmetry code: (i) .