(Z)-1-Chloro-1-[2-(2-nitro-phen-yl)hydrazinyl-idene]propan-2-one.

The title mol-ecule, C9H8ClN3O3, lies on a mirror plane. Intra-molecular N-H⋯O and N-H⋯Cl hydrogen bonds occur. One of the nitro O atoms is disordered (site occupancy ratio = 0.40:0.10).

Related literature

For details of the synthesis and for the importance of hydrazonoyl halides in organic synthesis and their biological activity and metabolism, see: Awadallah et al. (2006 ▶, 2008 ▶); Budarina et al. (2007 ▶); Shawalia et al. (2009 ▶); Thaher et al. (2002 ▶).

Experimental

Crystal data

C9H8ClN3O3

M = 241.63

Orthorhombic,

a = 14.1344 (10) Å

b = 6.5420 (5) Å

c = 11.3748 (8) Å

V = 1051.80 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 173 K

0.25 × 0.13 × 0.05 mm

Data collection

Bruker APEXII diffractometer

6908 measured reflections

1365 independent reflections

1003 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.05

1365 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049938/rn2108sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049938/rn2108Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049938/rn2108Isup3.cml

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

C9H8ClN3O3	F(000) = 496
Mr = 241.63	Dx = 1.526 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1147 reflections
a = 14.1344 (10) Å	θ = 2.3–25.8°
b = 6.5420 (5) Å	µ = 0.36 mm−1
c = 11.3748 (8) Å	T = 173 K
V = 1051.80 (13) Å3	Needle, yellow
Z = 4	0.25 × 0.13 × 0.05 mm

Bruker APEXII diffractometer	1003 reflections with I > 2σ(I)
Radiation source: sealed Tube	Rint = 0.045
Graphite monochromator	θmax = 27.9°, θmin = 2.3°
CCD scan	h = −18→18
6908 measured reflections	k = −8→8
1365 independent reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.198P] where P = (Fo2 + 2Fc2)/3
1365 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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	Occ. (<1)
Cl1	0.17306 (5)	0.2500	0.30944 (6)	0.0416 (3)
C1	−0.00994 (17)	0.2500	0.0079 (2)	0.0227 (5)
C2	0.02943 (17)	0.2500	−0.1054 (2)	0.0240 (5)
C3	−0.02668 (19)	0.2500	−0.2057 (2)	0.0276 (6)
H3	0.0012	0.2500	−0.2798	0.033*
C4	−0.12361 (18)	0.2500	−0.1949 (2)	0.0294 (6)
H4	−0.1617	0.2500	−0.2616	0.035*
C5	−0.16419 (17)	0.2500	−0.0832 (2)	0.0302 (6)
H5	−0.2297	0.2500	−0.0759	0.036*
C6	−0.10892 (18)	0.2500	0.0161 (2)	0.0268 (6)
H6	−0.1375	0.2500	0.0898	0.032*
N7	0.13162 (16)	0.2500	−0.1243 (2)	0.0357 (6)
O8	0.18551 (13)	0.2500	−0.04010 (17)	0.0413 (5)
O9	0.1605 (11)	0.2922 (10)	−0.2234 (15)	0.031 (9)	0.40
O9B	0.156 (5)	0.135 (13)	−0.225 (6)	0.033 (15)	0.10
N10	0.04475 (14)	0.2500	0.10920 (17)	0.0270 (5)
H10	0.1106	0.2500	0.1091	0.040*
N11	0.00142 (15)	0.2500	0.21389 (18)	0.0259 (5)
C12	0.05021 (18)	0.2500	0.3081 (2)	0.0277 (6)
C13	0.0018 (2)	0.2500	0.4244 (2)	0.0362 (7)
O14	0.04865 (17)	0.2500	0.51438 (17)	0.0502 (6)
C15	−0.1042 (2)	0.2500	0.4226 (3)	0.0517 (9)
H15A	−0.1274	0.2500	0.5019	0.078*
H15B	−0.1265	0.1302	0.3826	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.0303 (4)	0.0640 (5)	0.0305 (4)	0.000	−0.0087 (3)	0.000
C1	0.0224 (12)	0.0260 (13)	0.0198 (11)	0.000	−0.0032 (9)	0.000
C2	0.0186 (11)	0.0320 (14)	0.0215 (12)	0.000	0.0008 (9)	0.000
C3	0.0321 (13)	0.0315 (14)	0.0192 (12)	0.000	0.0016 (10)	0.000
C4	0.0270 (13)	0.0376 (15)	0.0236 (13)	0.000	−0.0081 (11)	0.000
C5	0.0196 (11)	0.0413 (16)	0.0297 (14)	0.000	−0.0047 (10)	0.000
C6	0.0234 (12)	0.0373 (15)	0.0197 (12)	0.000	0.0029 (10)	0.000
N7	0.0293 (12)	0.0544 (16)	0.0235 (12)	0.000	0.0018 (10)	0.000
O8	0.0236 (10)	0.0659 (15)	0.0344 (11)	0.000	−0.0027 (9)	0.000
O9	0.031 (2)	0.03 (3)	0.028 (2)	0.002 (5)	0.0129 (16)	0.006 (6)
O9B	0.040 (10)	0.03 (4)	0.027 (8)	−0.010 (18)	0.001 (7)	−0.016 (19)
N10	0.0214 (10)	0.0401 (13)	0.0194 (10)	0.000	−0.0004 (8)	0.000
N11	0.0265 (11)	0.0307 (12)	0.0206 (10)	0.000	0.0007 (9)	0.000
C12	0.0277 (13)	0.0352 (15)	0.0203 (13)	0.000	−0.0011 (10)	0.000
C13	0.0430 (16)	0.0457 (18)	0.0199 (12)	0.000	0.0012 (12)	0.000
O14	0.0572 (14)	0.0749 (17)	0.0186 (10)	0.000	−0.0033 (10)	0.000
C15	0.0446 (18)	0.079 (3)	0.0315 (17)	0.000	0.0111 (15)	0.000

Cl1—C12	1.736 (3)	N7—O9	1.230 (16)
C1—N10	1.388 (3)	N7—O9i	1.230 (16)
C1—C6	1.402 (3)	N7—O9B	1.42 (6)
C1—C2	1.403 (3)	N7—O9Bi	1.42 (6)
C2—C3	1.390 (3)	O9—O9i	0.553 (13)
C2—N7	1.460 (3)	O9B—O9Bi	1.50 (17)
C3—C4	1.376 (4)	N10—N11	1.339 (3)
C3—H3	0.9300	N10—H10	0.9315
C4—C5	1.394 (4)	N11—C12	1.275 (3)
C4—H4	0.9300	C12—C13	1.489 (4)
C5—C6	1.374 (3)	C13—O14	1.220 (3)
C5—H5	0.9300	C13—C15	1.497 (4)
C6—H6	0.9300	C15—H15A	0.9600
N7—O8	1.224 (3)	C15—H15B	0.9600
N10—C1—C6	120.0 (2)	O8—N7—O9Bi	119 (3)
N10—C1—C2	122.8 (2)	O9—N7—O9Bi	19 (3)
C6—C1—C2	117.2 (2)	O9i—N7—O9Bi	45 (4)
C3—C2—C1	121.8 (2)	O9B—N7—O9Bi	64 (7)
C3—C2—N7	116.3 (2)	O8—N7—C2	120.0 (2)
C1—C2—N7	121.8 (2)	O9—N7—C2	117.6 (8)
C4—C3—C2	119.7 (2)	O9i—N7—C2	117.6 (8)
C4—C3—H3	120.2	O9B—N7—C2	111 (2)
C2—C3—H3	120.2	O9Bi—N7—C2	111 (2)
C3—C4—C5	119.4 (2)	O9i—O9—N7	77.0 (3)
C3—C4—H4	120.3	N7—O9B—O9Bi	58 (4)
C5—C4—H4	120.3	N11—N10—C1	118.9 (2)
C6—C5—C4	121.1 (2)	N11—N10—H10	117.3
C6—C5—H5	119.5	C1—N10—H10	123.8
C4—C5—H5	119.5	C12—N11—N10	120.0 (2)
C5—C6—C1	120.8 (2)	N11—C12—C13	119.9 (2)
C5—C6—H6	119.6	N11—C12—Cl1	123.26 (19)
C1—C6—H6	119.6	C13—C12—Cl1	116.89 (18)
O8—N7—O9	120.7 (8)	O14—C13—C12	119.7 (3)
O8—N7—O9i	120.7 (8)	O14—C13—C15	123.7 (3)
O9—N7—O9i	26.0 (6)	C12—C13—C15	116.6 (2)
O8—N7—O9B	119 (3)	C13—C15—H15A	109.2
O9—N7—O9B	45 (4)	C13—C15—H15B	109.6
O9i—N7—O9B	19 (3)	H15A—C15—H15B	109.5
N10—C1—C2—C3	180.0	C3—C2—N7—O9Bi	35 (4)
C6—C1—C2—C3	−0.0	C1—C2—N7—O9Bi	−145 (4)
N10—C1—C2—N7	−0.0	O8—N7—O9—O9i	97.9 (3)
C6—C1—C2—N7	180.0	O9B—N7—O9—O9i	−4 (5)
C1—C2—C3—C4	0.0	O9Bi—N7—O9—O9i	−172 (11)
N7—C2—C3—C4	180.0	C2—N7—O9—O9i	−96.9 (3)
C2—C3—C4—C5	−0.0	O8—N7—O9B—O9Bi	−110 (2)
C3—C4—C5—C6	0.0	O9—N7—O9B—O9Bi	−4 (6)
C4—C5—C6—C1	−0.0	O9i—N7—O9B—O9Bi	−9 (13)
N10—C1—C6—C5	180.0	C2—N7—O9B—O9Bi	104 (3)
C2—C1—C6—C5	0.0	C6—C1—N10—N11	−0.0
C3—C2—N7—O8	180.0	C2—C1—N10—N11	180.0
C1—C2—N7—O8	0.0	C1—N10—N11—C12	180.0
C3—C2—N7—O9	14.7 (4)	N10—N11—C12—C13	180.0
C1—C2—N7—O9	−165.3 (4)	N10—N11—C12—Cl1	−0.0
C3—C2—N7—O9i	−14.7 (4)	N11—C12—C13—O14	180.0
C1—C2—N7—O9i	165.3 (4)	Cl1—C12—C13—O14	0.0
C3—C2—N7—O9B	−35 (4)	N11—C12—C13—C15	−0.0
C1—C2—N7—O9B	145 (4)	Cl1—C12—C13—C15	180.0

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···Cl1	0.93	2.44	2.912 (2)	111
N10—H10···O8	0.93	2.00	2.616 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯Cl1	0.93	2.44	2.912 (2)	111
N10—H10⋯O8	0.93	2.00	2.616 (3)	122