4-[(E)-(3-Chloro-4-methyl-phen-yl)imino-meth-yl]-2-methoxy-3-nitro-phenyl acetate.

The title compound, C(17)H(15)ClN(2)O(5), displays a trans-configuration with respect to the C=N double bond. The mol-ecule is twisted, the dihedral angle between the mean planes of the two benzene rings being 18.70 (12)°. The nitro, meth-oxy and acetyl groups are oriented at 80.70 (11), 35.2 (2) and 72.35 (10)°, respectively, to the benzene ring to which they are bonded. The crystal structure is stabilized by weak C-H⋯O hydrogen-bonding contacts.

Related literature

For background to Schiff bases in coordination chemistry, see: Bhatia et al. (1981 ▶); Costamagna et al. (1992 ▶). For a related structure, see: Qian & Liu (2010 ▶).

Experimental

Crystal data

C17H15ClN2O5

M = 362.76

Triclinic,

a = 7.035 (6) Å

b = 7.672 (6) Å

c = 17.272 (14) Å

α = 83.477 (8)°

β = 84.994 (8)°

γ = 66.697 (7)°

V = 849.7 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.26 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.936, T max = 0.948

5579 measured reflections

3083 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 1.05

3083 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811055590/pv2498sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055590/pv2498Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055590/pv2498Isup3.cml

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

C17H15ClN2O5	Z = 2
Mr = 362.76	F(000) = 376
Triclinic, P1	Dx = 1.418 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.035 (6) Å	Cell parameters from 3083 reflections
b = 7.672 (6) Å	θ = 2.4–25.5°
c = 17.272 (14) Å	µ = 0.26 mm−1
α = 83.477 (8)°	T = 296 K
β = 84.994 (8)°	Block, yellow
γ = 66.697 (7)°	0.26 × 0.23 × 0.21 mm
V = 849.7 (12) Å3

Bruker APEXII CCD diffractometer	3083 independent reflections
Radiation source: fine-focus sealed tube	2207 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.936, Tmax = 0.948	k = −9→9
5579 measured reflections	l = −20→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4254P] where P = (Fo2 + 2Fc2)/3
3083 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.17 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	−0.50222 (11)	1.23475 (11)	0.05852 (6)	0.0880 (3)
O1	−0.3219 (3)	0.5157 (3)	0.34263 (13)	0.0728 (6)
O2	−0.3928 (3)	0.4212 (3)	0.23925 (14)	0.0733 (6)
O3	−0.2466 (2)	0.0650 (2)	0.34480 (11)	0.0563 (5)
O4	0.1492 (2)	−0.2520 (2)	0.35298 (10)	0.0472 (4)
O5	0.2885 (4)	−0.2451 (3)	0.46343 (13)	0.0891 (8)
N1	−0.0690 (3)	0.6082 (3)	0.20244 (12)	0.0450 (5)
N2	−0.2784 (3)	0.4109 (3)	0.28994 (14)	0.0490 (5)
C1	−0.2521 (3)	0.9075 (3)	0.13350 (15)	0.0491 (6)
H1	−0.3684	0.8771	0.1395	0.059*
C2	−0.2654 (4)	1.0797 (3)	0.09522 (15)	0.0491 (6)
C3	−0.0985 (4)	1.1342 (3)	0.08453 (14)	0.0459 (6)
C4	0.0867 (4)	1.0021 (4)	0.11302 (15)	0.0510 (6)
H4	0.2035	1.0317	0.1061	0.061*
C5	0.1053 (4)	0.8288 (3)	0.15121 (15)	0.0472 (6)
H5	0.2328	0.7443	0.1692	0.057*
C6	−0.0665 (3)	0.7799 (3)	0.16295 (13)	0.0405 (5)
C7	0.0954 (3)	0.4730 (3)	0.22155 (15)	0.0469 (6)
H7	0.2197	0.4885	0.2100	0.056*
C8	0.1029 (3)	0.2917 (3)	0.26103 (14)	0.0411 (5)
C9	−0.0705 (3)	0.2553 (3)	0.29035 (13)	0.0377 (5)
C10	−0.0619 (3)	0.0795 (3)	0.32370 (13)	0.0390 (5)
C11	0.1336 (3)	−0.0677 (3)	0.32809 (14)	0.0404 (5)
C12	0.3094 (3)	−0.0359 (3)	0.30170 (15)	0.0492 (6)
H12	0.4389	−0.1349	0.3063	0.059*
C13	0.2947 (3)	0.1401 (3)	0.26888 (16)	0.0505 (6)
H13	0.4148	0.1587	0.2515	0.061*
C14	−0.1131 (5)	1.3253 (4)	0.04590 (17)	0.0626 (8)
H14A	0.0227	1.3280	0.0397	0.094*
H14B	−0.2006	1.4239	0.0778	0.094*
H14C	−0.1706	1.3456	−0.0043	0.094*
C15	−0.2664 (4)	−0.0543 (4)	0.41121 (17)	0.0644 (8)
H15A	−0.2223	−0.1825	0.3972	0.097*
H15B	−0.4086	−0.0101	0.4301	0.097*
H15C	−0.1817	−0.0511	0.4513	0.097*
C16	0.2390 (4)	−0.3320 (4)	0.42227 (17)	0.0568 (7)
C17	0.2612 (5)	−0.5342 (4)	0.43672 (19)	0.0748 (9)
H17A	0.2924	−0.5781	0.4902	0.112*
H17B	0.3714	−0.6114	0.4033	0.112*
H17C	0.1340	−0.5434	0.4260	0.112*

	U11	U22	U33	U12	U13	U23
Cl1	0.0514 (4)	0.0650 (5)	0.1311 (8)	−0.0151 (3)	−0.0205 (4)	0.0421 (5)
O1	0.0657 (13)	0.0466 (11)	0.0789 (15)	0.0036 (9)	0.0188 (11)	−0.0090 (11)
O2	0.0380 (10)	0.0623 (12)	0.1146 (18)	−0.0145 (9)	−0.0277 (11)	0.0122 (11)
O3	0.0386 (9)	0.0504 (10)	0.0747 (13)	−0.0175 (8)	−0.0028 (8)	0.0165 (9)
O4	0.0476 (9)	0.0301 (8)	0.0579 (11)	−0.0087 (7)	−0.0108 (8)	0.0025 (7)
O5	0.121 (2)	0.0643 (14)	0.0713 (15)	−0.0178 (13)	−0.0387 (14)	−0.0035 (11)
N1	0.0378 (10)	0.0385 (11)	0.0580 (13)	−0.0158 (8)	−0.0069 (9)	0.0048 (9)
N2	0.0326 (10)	0.0328 (11)	0.0714 (15)	−0.0065 (8)	0.0028 (11)	0.0088 (11)
C1	0.0351 (12)	0.0438 (14)	0.0662 (17)	−0.0165 (10)	−0.0007 (11)	0.0069 (12)
C2	0.0408 (13)	0.0429 (14)	0.0576 (16)	−0.0130 (10)	−0.0023 (11)	0.0067 (12)
C3	0.0551 (14)	0.0434 (13)	0.0429 (14)	−0.0247 (11)	−0.0005 (11)	0.0003 (11)
C4	0.0502 (14)	0.0562 (15)	0.0571 (16)	−0.0331 (12)	−0.0053 (12)	0.0024 (12)
C5	0.0400 (12)	0.0464 (14)	0.0578 (15)	−0.0200 (11)	−0.0085 (11)	0.0024 (12)
C6	0.0407 (12)	0.0370 (12)	0.0444 (13)	−0.0168 (10)	−0.0012 (10)	−0.0007 (10)
C7	0.0319 (12)	0.0392 (13)	0.0702 (17)	−0.0153 (10)	−0.0014 (11)	−0.0024 (12)
C8	0.0311 (11)	0.0332 (12)	0.0575 (15)	−0.0103 (9)	−0.0066 (10)	−0.0031 (10)
C9	0.0276 (10)	0.0284 (11)	0.0510 (14)	−0.0039 (8)	−0.0048 (10)	−0.0025 (10)
C10	0.0319 (11)	0.0354 (12)	0.0474 (14)	−0.0105 (9)	−0.0040 (10)	−0.0023 (10)
C11	0.0423 (12)	0.0276 (11)	0.0478 (14)	−0.0087 (9)	−0.0110 (10)	−0.0014 (10)
C12	0.0313 (12)	0.0365 (13)	0.0714 (17)	−0.0030 (10)	−0.0127 (11)	−0.0022 (12)
C13	0.0290 (11)	0.0395 (13)	0.0805 (19)	−0.0104 (10)	−0.0060 (11)	−0.0035 (12)
C14	0.0789 (19)	0.0525 (16)	0.0637 (18)	−0.0371 (15)	−0.0055 (15)	0.0103 (14)
C15	0.0564 (16)	0.0651 (18)	0.0666 (19)	−0.0235 (14)	0.0067 (14)	0.0065 (15)
C16	0.0533 (15)	0.0428 (15)	0.0562 (17)	−0.0006 (12)	−0.0052 (13)	0.0015 (13)
C17	0.0739 (19)	0.0481 (16)	0.084 (2)	−0.0107 (14)	−0.0018 (16)	0.0189 (15)

Cl1—C2	1.743 (3)	C7—C8	1.461 (3)
O1—N2	1.221 (3)	C7—H7	0.9300
O2—N2	1.215 (3)	C8—C13	1.395 (3)
O3—C10	1.362 (3)	C8—C9	1.397 (3)
O3—C15	1.417 (3)	C9—C10	1.386 (3)
O4—C16	1.366 (3)	C10—C11	1.394 (3)
O4—C11	1.394 (3)	C11—C12	1.382 (3)
O5—C16	1.186 (3)	C12—C13	1.372 (3)
N1—C7	1.250 (3)	C12—H12	0.9300
N1—C6	1.419 (3)	C13—H13	0.9300
N2—C9	1.478 (3)	C14—H14A	0.9600
C1—C2	1.381 (3)	C14—H14B	0.9600
C1—C6	1.383 (3)	C14—H14C	0.9600
C1—H1	0.9300	C15—H15A	0.9600
C2—C3	1.386 (4)	C15—H15B	0.9600
C3—C4	1.386 (3)	C15—H15C	0.9600
C3—C14	1.508 (3)	C16—C17	1.490 (4)
C4—C5	1.378 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.393 (3)	C17—H17C	0.9600
C5—H5	0.9300
C10—O3—C15	120.89 (19)	O3—C10—C9	116.62 (18)
C16—O4—C11	117.65 (19)	O3—C10—C11	126.4 (2)
C7—N1—C6	121.1 (2)	C9—C10—C11	116.9 (2)
O2—N2—O1	125.6 (2)	C12—C11—C10	120.7 (2)
O2—N2—C9	118.1 (2)	C12—C11—O4	119.86 (19)
O1—N2—C9	116.3 (2)	C10—C11—O4	119.2 (2)
C2—C1—C6	120.3 (2)	C13—C12—C11	120.7 (2)
C2—C1—H1	119.9	C13—C12—H12	119.6
C6—C1—H1	119.9	C11—C12—H12	119.6
C1—C2—C3	122.8 (2)	C12—C13—C8	121.2 (2)
C1—C2—Cl1	118.53 (19)	C12—C13—H13	119.4
C3—C2—Cl1	118.66 (19)	C8—C13—H13	119.4
C4—C3—C2	115.7 (2)	C3—C14—H14A	109.5
C4—C3—C14	120.9 (2)	C3—C14—H14B	109.5
C2—C3—C14	123.4 (2)	H14A—C14—H14B	109.5
C5—C4—C3	122.8 (2)	C3—C14—H14C	109.5
C5—C4—H4	118.6	H14A—C14—H14C	109.5
C3—C4—H4	118.6	H14B—C14—H14C	109.5
C4—C5—C6	120.2 (2)	O3—C15—H15A	109.5
C4—C5—H5	119.9	O3—C15—H15B	109.5
C6—C5—H5	119.9	H15A—C15—H15B	109.5
C1—C6—C5	118.1 (2)	O3—C15—H15C	109.5
C1—C6—N1	116.1 (2)	H15A—C15—H15C	109.5
C5—C6—N1	125.7 (2)	H15B—C15—H15C	109.5
N1—C7—C8	123.6 (2)	O5—C16—O4	122.1 (3)
N1—C7—H7	118.2	O5—C16—C17	127.0 (3)
C8—C7—H7	118.2	O4—C16—C17	110.9 (3)
C13—C8—C9	116.4 (2)	C16—C17—H17A	109.5
C13—C8—C7	118.9 (2)	C16—C17—H17B	109.5
C9—C8—C7	124.71 (19)	H17A—C17—H17B	109.5
C10—C9—C8	124.07 (18)	C16—C17—H17C	109.5
C10—C9—N2	115.70 (19)	H17A—C17—H17C	109.5
C8—C9—N2	120.18 (19)	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O4	0.96	2.52	2.861 (4)	101
C12—H12···O1i	0.93	2.58	3.431 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.58	3.431 (3)	153

Symmetry code: (i) .