Ethyl (Z)-2-chloro-2-(2-phenyl-hydrazin-1-yl-idene)acetate.

The title compound, C(10)H(11)ClN(2)O(2), features an almost planar C(ar)-N(H)-N=C(Cl) unit [torsion angle = 0.8 (1)° whose phenyl substituent is almost coplanar with it [dihedral angle = 2.8 (2)°]; this unit is slightly twisted with respect to the carboxyl -CO(2) fragment [dihedral angle = 10.3 (2)°]. In the crystal, the amino group acts as a hydrogen-bond donor to the carbonyl O atom of an adjacent mol-ecule; the hydrogen bond generates a helical chain that runs along the b axis of the monoclinic unit cell.

Related literature

For a review of the reactions of hydrazonyl halides with heterocyclic thio­nes for heteroannulation, the synthesis of spiro­heterocycles and heterocyclic ring formation, see: Shawali & Farghaly (2008 ▶). For related crystal structures, see: Xu (2006 ▶); Yin et al. (2006 ▶).

Experimental

Crystal data

C10H11ClN2O2

M = 226.66

Monoclinic,

a = 10.5091 (7) Å

b = 11.1813 (8) Å

c = 10.1190 (7) Å

β = 118.148 (1)°

V = 1048.41 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.30 × 0.30 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.904, T max = 0.966

6532 measured reflections

2399 independent reflections

2191 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.076

S = 1.03

2399 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and n class="Chemical">constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: n class="Gene">APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032587/nk2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032587/nk2054Isup2.hkl

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

C10H11ClN2O2	F(000) = 472
Mr = 226.66	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4259 reflections
a = 10.5091 (7) Å	θ = 2.3–28.3°
b = 11.1813 (8) Å	µ = 0.35 mm−1
c = 10.1190 (7) Å	T = 100 K
β = 118.148 (1)°	Irregular, yellow
V = 1048.41 (13) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	2191 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.904, Tmax = 0.966	k = −14→12
6532 measured reflections	l = −13→13

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.389P] where P = (Fo2 + 2Fc2)/3
2399 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.52913 (3)	0.54445 (2)	0.33899 (3)	0.02076 (10)
O1	0.67383 (8)	0.38123 (7)	0.09626 (9)	0.01737 (18)
O2	0.49929 (9)	0.33068 (7)	0.15554 (9)	0.01943 (19)
N1	0.70432 (10)	0.70808 (8)	0.26261 (10)	0.0153 (2)
H1	0.6608 (17)	0.7284 (15)	0.3121 (17)	0.032 (4)*
N2	0.68722 (10)	0.59913 (8)	0.20434 (10)	0.01443 (19)
C1	0.78999 (11)	0.79127 (10)	0.23651 (11)	0.0143 (2)
C2	0.81229 (12)	0.90363 (10)	0.30391 (12)	0.0171 (2)
H2	0.7691	0.9232	0.3651	0.020*
C3	0.89810 (12)	0.98666 (11)	0.28081 (13)	0.0201 (2)
H3	0.9140	1.0629	0.3273	0.024*
C4	0.96101 (13)	0.95973 (11)	0.19073 (14)	0.0208 (2)
H4	1.0194	1.0170	0.1753	0.025*
C5	0.93736 (12)	0.84780 (11)	0.12342 (13)	0.0201 (2)
H5	0.9796	0.8289	0.0612	0.024*
C6	0.85275 (12)	0.76310 (10)	0.14599 (12)	0.0167 (2)
H6	0.8378	0.6866	0.1001	0.020*
C7	0.61141 (12)	0.52090 (10)	0.22737 (12)	0.0152 (2)
C8	0.58682 (11)	0.40102 (10)	0.15624 (12)	0.0147 (2)
C9	0.66715 (12)	0.26082 (10)	0.03770 (13)	0.0176 (2)
H9A	0.5698	0.2446	−0.0461	0.021*
H9B	0.6887	0.2006	0.1172	0.021*
C10	0.77830 (12)	0.25572 (12)	−0.01594 (13)	0.0213 (3)
H10A	0.7777	0.1760	−0.0566	0.032*
H10B	0.8740	0.2719	0.0681	0.032*
H10C	0.7557	0.3159	−0.0943	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.02594 (16)	0.01667 (16)	0.02897 (16)	−0.00155 (10)	0.02060 (13)	−0.00199 (10)
O1	0.0184 (4)	0.0141 (4)	0.0232 (4)	−0.0018 (3)	0.0128 (3)	−0.0032 (3)
O2	0.0200 (4)	0.0155 (4)	0.0260 (4)	−0.0020 (3)	0.0136 (3)	0.0007 (3)
N1	0.0167 (4)	0.0138 (5)	0.0185 (4)	−0.0005 (4)	0.0109 (4)	−0.0015 (3)
N2	0.0133 (4)	0.0130 (5)	0.0153 (4)	0.0013 (3)	0.0053 (3)	0.0007 (3)
C1	0.0109 (5)	0.0151 (5)	0.0148 (5)	0.0005 (4)	0.0043 (4)	0.0024 (4)
C2	0.0165 (5)	0.0163 (6)	0.0187 (5)	0.0016 (4)	0.0087 (4)	0.0002 (4)
C3	0.0187 (5)	0.0144 (5)	0.0249 (6)	−0.0006 (4)	0.0084 (5)	0.0001 (4)
C4	0.0164 (5)	0.0202 (6)	0.0247 (6)	−0.0026 (4)	0.0090 (5)	0.0044 (4)
C5	0.0172 (5)	0.0250 (6)	0.0201 (5)	0.0002 (5)	0.0105 (4)	0.0017 (4)
C6	0.0163 (5)	0.0169 (5)	0.0170 (5)	−0.0002 (4)	0.0078 (4)	−0.0007 (4)
C7	0.0144 (5)	0.0162 (5)	0.0166 (5)	0.0020 (4)	0.0087 (4)	0.0011 (4)
C8	0.0139 (5)	0.0149 (5)	0.0146 (5)	0.0018 (4)	0.0061 (4)	0.0025 (4)
C9	0.0184 (5)	0.0151 (5)	0.0200 (5)	0.0000 (4)	0.0098 (4)	−0.0022 (4)
C10	0.0189 (6)	0.0241 (6)	0.0221 (6)	−0.0015 (5)	0.0107 (5)	−0.0062 (5)

Cl1—C7	1.7361 (11)	C3—H3	0.9500
O1—C8	1.3331 (13)	C4—C5	1.3900 (17)
O1—C9	1.4593 (13)	C4—H4	0.9500
O2—C8	1.2076 (14)	C5—C6	1.3897 (16)
N1—N2	1.3282 (13)	C5—H5	0.9500
N1—C1	1.4035 (14)	C6—H6	0.9500
N1—H1	0.853 (13)	C7—C8	1.4853 (15)
N2—C7	1.2765 (14)	C9—C10	1.5035 (15)
C1—C2	1.3957 (16)	C9—H9A	0.9900
C1—C6	1.3939 (15)	C9—H9B	0.9900
C2—C3	1.3888 (16)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C3—C4	1.3883 (17)	C10—H10C	0.9800
C8—O1—C9	115.22 (8)	C5—C6—H6	120.3
N2—N1—C1	119.25 (9)	C1—C6—H6	120.3
N2—N1—H1	120.4 (11)	N2—C7—C8	120.72 (10)
C1—N1—H1	120.3 (11)	N2—C7—Cl1	124.07 (9)
C7—N2—N1	120.85 (9)	C8—C7—Cl1	115.21 (8)
C2—C1—C6	120.14 (10)	O2—C8—O1	124.99 (10)
C2—C1—N1	118.64 (10)	O2—C8—C7	123.26 (10)
C6—C1—N1	121.22 (10)	O1—C8—C7	111.74 (9)
C3—C2—C1	119.48 (10)	O1—C9—C10	106.55 (9)
C3—C2—H2	120.3	O1—C9—H9A	110.4
C1—C2—H2	120.3	C10—C9—H9A	110.4
C4—C3—C2	120.91 (11)	O1—C9—H9B	110.4
C4—C3—H3	119.5	C10—C9—H9B	110.4
C2—C3—H3	119.5	H9A—C9—H9B	108.6
C5—C4—C3	119.11 (11)	C9—C10—H10A	109.5
C5—C4—H4	120.4	C9—C10—H10B	109.5
C3—C4—H4	120.4	H10A—C10—H10B	109.5
C4—C5—C6	120.89 (11)	C9—C10—H10C	109.5
C4—C5—H5	119.6	H10A—C10—H10C	109.5
C6—C5—H5	119.6	H10B—C10—H10C	109.5
C5—C6—C1	119.46 (11)
C1—N1—N2—C7	179.17 (10)	N1—C1—C6—C5	−179.74 (10)
N2—N1—C1—C2	−177.17 (9)	N1—N2—C7—C8	177.11 (9)
N2—N1—C1—C6	2.49 (15)	N1—N2—C7—Cl1	−2.23 (15)
C6—C1—C2—C3	−0.40 (16)	C9—O1—C8—O2	−5.24 (15)
N1—C1—C2—C3	179.26 (10)	C9—O1—C8—C7	173.93 (9)
C1—C2—C3—C4	0.50 (17)	N2—C7—C8—O2	−168.44 (10)
C2—C3—C4—C5	−0.11 (17)	Cl1—C7—C8—O2	10.96 (14)
C3—C4—C5—C6	−0.38 (17)	N2—C7—C8—O1	12.38 (14)
C4—C5—C6—C1	0.47 (17)	Cl1—C7—C8—O1	−168.22 (7)
C2—C1—C6—C5	−0.08 (16)	C8—O1—C9—C10	−176.85 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.85 (1)	2.18 (1)	2.969 (1)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.85 (1)	2.18 (1)	2.969 (1)	153 (2)

Symmetry code: (i) .