(E)-N′-[4-(2,4-Dichloro­benz­yloxy)-3-methoxy­benzyl­idene]-2-methoxy­benzohydrazide sesquihydrate

Liu, S.-X.; Tian, X.; Zhen, X.-L.; Li, Z.-C.; Han, J.-R.

doi:10.1107/S1600536807051070

(E)-N′-[4-(2,4-Dichlorobenzyloxy)-3-methoxybenzylidene]-2-methoxybenzohydrazide sesquihydrate

S.-X. Liu, X. Tian, X.-L. Zhen, Z.-C. Li and J.-R. Han

In the title compound, C₂₃H₂₀Cl₂N₂O₄·1.5H₂O, the vanillin group makes dihedral angles of 0.52 (14) and 81.22 (7)° with the benzohydrazide residue and the dichlorobenzene ring, respectively. An intramolecular N—H

O hydrogen bond helps to stabilize the molecular conformation, while intermolecular O—H

O and bifurcated O—H

(N,O) hydrogen bonds link the molecules, forming an infinite network. One of the water molecule sites is half-occupied.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051070/hb2588sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051070/hb2588Isup2.hkl Contains datablock I

CCDC reference: 667415

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.049
wR factor = 0.130
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1A    ..  H2B     ..       2.05 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). As part of an investigation of the coordination properties of Schiff bases functioning as ligands, we report the synthesis and structure of the title compound, (I).

In (I) (Fig. 1), the vanillin group (C21—C27/O21/O22) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0229 Å. This plane makes dihedral angles of 0.52 (14)° and 81.22 (7)° with the benzohydrazide residue (C11—C16) and the dichlorobenzene ring (C31—C36), respectively. The dihedral angle between the benzohydrazide residue and the dichlorobenzene ring is 81.74 (9)°. Otherwise, all bond lengths and angles are within normal ranges (Allen et al., 1987).

An intramolecular hydrogen bond links the NH group to O12, thereby influencing the molecular conformation (Table 1). A bifurcated O—H···(N,O) and an O—H···O hydrogen bond link the water molecules to the main molecule, resulting in dimeric associations of two main molecules and two water molecules. Then, further O—H···O hydrogen bonds link the molecules into an infinite network (Fig. 2).

Related literature top

For general background, Santos et al. (2001). For reference structural data, see: Allen et al. (1987).

Experimental top

An anhydrous ethanol solution (50 ml) of 4-(2,4-dichlorobenzyloxy)-3-methoxybenzaldehyde (3.11 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 2-methoxybenzohydrazide (1.66 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a white precipitate. The product was isolated, recrystallized from ethanol and then dried in a vacuum to give the pure compound in 81% yield. Colourless blocks of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution. Presumably the water of crystallization in (I) was absorbed from the atmosphere.

Structure description top

For general background, Santos et al. (2001). For reference structural data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines. For the sake of clarity, H atoms bonded to C atoms have been omitted.

(E)—N'-[4-(2,4-Dichlorobenzyloxy)-3-methoxybenzylidene]-2-methoxybenzohydrazide sesquihydrate top

Crystal data top

C₂₃H₂₀Cl₂N₂O₄·1.5H₂O	Z = 2
M_r = 486.34	F(000) = 506
Triclinic, P1	D_x = 1.408 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7689 (16) Å	Cell parameters from 1784 reflections
b = 8.3390 (17) Å	θ = 2.3–25.6°
c = 18.345 (4) Å	µ = 0.33 mm⁻¹
α = 80.93 (3)°	T = 294 K
β = 77.85 (3)°	Block, colorless
γ = 86.50 (3)°	0.24 × 0.20 × 0.18 mm
V = 1146.9 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	4015 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→9
T_min = 0.902, T_max = 0.943	k = −9→9
5880 measured reflections	l = −21→21

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0509P)² + 0.5064P] where P = (F_o² + 2F_c²)/3
4015 reflections	(Δ/σ)_max < 0.001
295 parameters	Δρ_max = 0.45 e Å⁻³
6 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₃H₂₀Cl₂N₂O₄·1.5H₂O	γ = 86.50 (3)°
M_r = 486.34	V = 1146.9 (4) Å³
Triclinic, P1	Z = 2
a = 7.7689 (16) Å	Mo Kα radiation
b = 8.3390 (17) Å	µ = 0.33 mm⁻¹
c = 18.345 (4) Å	T = 294 K
α = 80.93 (3)°	0.24 × 0.20 × 0.18 mm
β = 77.85 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4015 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2630 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.943	R_int = 0.022
5880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	6 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.02	Δρ_max = 0.45 e Å⁻³
4015 reflections	Δρ_min = −0.33 e Å⁻³
295 parameters

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	Occ. (<1)
Cl1	−0.13680 (11)	0.79097 (10)	0.38426 (5)	0.0694 (3)
Cl2	−0.39945 (15)	0.19415 (15)	0.47328 (6)	0.1037 (4)
N27	0.5507 (3)	0.2392 (3)	0.01833 (11)	0.0398 (5)
N17	0.5335 (3)	0.1920 (3)	−0.04870 (11)	0.0408 (5)
H17	0.4404	0.2209	−0.0663	0.049*
O21	0.3807 (2)	0.5372 (2)	0.32719 (10)	0.0482 (5)
O22	0.6607 (2)	0.3832 (3)	0.27045 (10)	0.0555 (5)
O17	0.7940 (3)	0.0557 (3)	−0.06310 (11)	0.0590 (6)
O12	0.3475 (2)	0.1888 (2)	−0.15247 (11)	0.0555 (5)
C24	0.4146 (3)	0.3881 (3)	0.11807 (13)	0.0367 (6)
C22	0.5358 (3)	0.4077 (3)	0.22718 (14)	0.0385 (6)
C11	0.6317 (3)	0.0618 (3)	−0.16009 (14)	0.0368 (6)
C26	0.2499 (3)	0.5272 (3)	0.21774 (14)	0.0401 (6)
H26	0.1491	0.5849	0.2375	0.048*
C25	0.2655 (3)	0.4755 (3)	0.14804 (14)	0.0408 (6)
H25	0.1755	0.4996	0.1213	0.049*
C17	0.6597 (3)	0.1018 (3)	−0.08664 (14)	0.0391 (6)
C21	0.3828 (3)	0.4934 (3)	0.25773 (14)	0.0385 (6)
C12	0.4826 (3)	0.1046 (3)	−0.19211 (15)	0.0406 (6)
C23	0.5507 (3)	0.3560 (3)	0.15837 (14)	0.0384 (6)
H23	0.6519	0.2992	0.1384	0.046*
C27	0.4222 (3)	0.3281 (3)	0.04695 (14)	0.0398 (6)
H27	0.3304	0.3555	0.0215	0.048*
C13	0.4770 (4)	0.0628 (3)	−0.26198 (16)	0.0495 (7)
H13	0.3790	0.0927	−0.2832	0.059*
C31	0.0713 (4)	0.5174 (3)	0.39109 (14)	0.0424 (7)
C16	0.7684 (3)	−0.0254 (3)	−0.20037 (15)	0.0434 (7)
H16	0.8676	−0.0564	−0.1801	0.052*
C14	0.6156 (4)	−0.0228 (4)	−0.30015 (16)	0.0532 (8)
H14	0.6103	−0.0505	−0.3468	0.064*
C37	0.2280 (4)	0.6251 (3)	0.36038 (15)	0.0472 (7)
H37A	0.1978	0.7116	0.3228	0.057*
H37B	0.2547	0.6746	0.4010	0.057*
C15	0.7606 (4)	−0.0670 (3)	−0.26974 (16)	0.0517 (8)
H15	0.8537	−0.1248	−0.2955	0.062*
C32	−0.1006 (4)	0.5803 (4)	0.40135 (14)	0.0469 (7)
C36	0.0922 (4)	0.3508 (4)	0.40978 (15)	0.0525 (8)
H36	0.2054	0.3046	0.4045	0.063*
C33	−0.2460 (4)	0.4836 (4)	0.42571 (16)	0.0584 (8)
H33	−0.3596	0.5288	0.4305	0.070*
C34	−0.2185 (5)	0.3197 (5)	0.44249 (16)	0.0617 (9)
C22A	0.8218 (4)	0.3038 (4)	0.24026 (19)	0.0682 (10)
H22A	0.7993	0.1941	0.2360	0.102*
H22B	0.9031	0.3032	0.2731	0.102*
H22C	0.8713	0.3607	0.1913	0.102*
C35	−0.0504 (5)	0.2514 (4)	0.43596 (16)	0.0621 (9)
H35	−0.0336	0.1400	0.4490	0.074*
C12A	0.1899 (4)	0.2271 (4)	−0.1805 (2)	0.0722 (10)
H12A	0.2160	0.2976	−0.2278	0.108*
H12B	0.1063	0.2805	−0.1450	0.108*
H12C	0.1411	0.1289	−0.1874	0.108*
O1	0.9358 (4)	0.1894 (3)	0.05343 (18)	0.1153 (11)
H1A	0.8732	0.1775	0.0217	0.138*
H1B	1.0302	0.1305	0.0513	0.138*
O2	0.0665 (6)	0.4574 (6)	0.9588 (3)	0.0901 (15)*	0.50
H2A	0.0498	0.5567	0.9654	0.108*	0.50
H2B	0.0095	0.3882	0.9929	0.108*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0655 (6)	0.0677 (6)	0.0727 (6)	0.0170 (4)	−0.0173 (4)	−0.0068 (4)
Cl2	0.0972 (8)	0.1244 (9)	0.0865 (7)	−0.0596 (7)	0.0000 (6)	−0.0102 (6)
N27	0.0412 (13)	0.0448 (13)	0.0342 (12)	−0.0012 (11)	−0.0058 (10)	−0.0108 (10)
N17	0.0413 (13)	0.0489 (14)	0.0343 (12)	0.0053 (11)	−0.0102 (10)	−0.0115 (10)
O21	0.0424 (11)	0.0659 (13)	0.0403 (11)	0.0044 (9)	−0.0078 (8)	−0.0230 (9)
O22	0.0390 (11)	0.0858 (15)	0.0483 (12)	0.0109 (10)	−0.0158 (9)	−0.0257 (11)
O17	0.0498 (12)	0.0776 (15)	0.0594 (13)	0.0183 (11)	−0.0236 (10)	−0.0311 (11)
O12	0.0440 (11)	0.0722 (14)	0.0567 (12)	0.0161 (10)	−0.0185 (10)	−0.0247 (11)
C24	0.0393 (15)	0.0366 (15)	0.0322 (14)	−0.0030 (12)	−0.0023 (11)	−0.0051 (11)
C22	0.0322 (14)	0.0448 (16)	0.0392 (15)	−0.0009 (12)	−0.0068 (12)	−0.0091 (12)
C11	0.0410 (15)	0.0322 (14)	0.0366 (14)	−0.0021 (12)	−0.0054 (12)	−0.0063 (11)
C26	0.0379 (15)	0.0429 (16)	0.0376 (15)	0.0040 (12)	−0.0024 (12)	−0.0095 (12)
C25	0.0403 (15)	0.0446 (16)	0.0369 (15)	0.0012 (13)	−0.0099 (12)	−0.0027 (12)
C17	0.0385 (15)	0.0382 (15)	0.0412 (15)	−0.0006 (12)	−0.0079 (12)	−0.0085 (12)
C21	0.0387 (15)	0.0427 (16)	0.0332 (14)	−0.0055 (12)	−0.0026 (12)	−0.0076 (12)
C12	0.0415 (16)	0.0376 (15)	0.0425 (16)	0.0025 (12)	−0.0072 (13)	−0.0088 (12)
C23	0.0331 (14)	0.0434 (16)	0.0376 (15)	0.0013 (12)	−0.0020 (11)	−0.0100 (12)
C27	0.0399 (15)	0.0443 (16)	0.0354 (15)	−0.0017 (13)	−0.0083 (12)	−0.0050 (12)
C13	0.0552 (18)	0.0507 (18)	0.0472 (17)	0.0017 (14)	−0.0199 (14)	−0.0100 (14)
C31	0.0510 (17)	0.0505 (18)	0.0267 (13)	0.0007 (14)	−0.0039 (12)	−0.0145 (12)
C16	0.0406 (16)	0.0410 (16)	0.0470 (17)	0.0021 (13)	−0.0049 (13)	−0.0080 (13)
C14	0.069 (2)	0.0534 (19)	0.0392 (16)	−0.0015 (16)	−0.0099 (15)	−0.0146 (14)
C37	0.0477 (17)	0.0549 (18)	0.0417 (16)	0.0031 (14)	−0.0049 (13)	−0.0228 (14)
C15	0.0593 (19)	0.0484 (18)	0.0462 (17)	0.0067 (15)	−0.0029 (15)	−0.0173 (14)
C32	0.0510 (18)	0.0581 (19)	0.0327 (15)	0.0012 (15)	−0.0084 (13)	−0.0111 (13)
C36	0.0581 (19)	0.057 (2)	0.0415 (16)	0.0014 (16)	−0.0054 (14)	−0.0129 (14)
C33	0.0478 (18)	0.085 (3)	0.0421 (17)	−0.0043 (18)	−0.0072 (14)	−0.0106 (17)
C34	0.070 (2)	0.076 (2)	0.0386 (17)	−0.0263 (19)	−0.0016 (15)	−0.0110 (16)
C22A	0.0397 (17)	0.103 (3)	0.070 (2)	0.0175 (17)	−0.0213 (16)	−0.032 (2)
C35	0.088 (3)	0.054 (2)	0.0407 (17)	−0.0094 (19)	−0.0046 (17)	−0.0075 (15)
C12A	0.052 (2)	0.092 (3)	0.083 (2)	0.0193 (18)	−0.0267 (18)	−0.034 (2)
O1	0.105 (2)	0.102 (2)	0.177 (3)	0.0502 (17)	−0.088 (2)	−0.080 (2)

Geometric parameters (Å, º) top

Cl1—C32	1.751 (3)	C13—H13	0.9300
Cl2—C34	1.747 (3)	C31—C36	1.386 (4)
N27—C27	1.279 (3)	C31—C32	1.391 (4)
N27—N17	1.383 (3)	C31—C37	1.513 (4)
N17—C17	1.341 (3)	C16—C15	1.385 (4)
N17—H17	0.8600	C16—H16	0.9300
O21—C21	1.377 (3)	C14—C15	1.365 (4)
O21—C37	1.431 (3)	C14—H14	0.9300
O22—C22	1.365 (3)	C37—H37A	0.9700
O22—C22A	1.426 (3)	C37—H37B	0.9700
O17—C17	1.229 (3)	C15—H15	0.9300
O12—C12	1.369 (3)	C32—C33	1.383 (4)
O12—C12A	1.425 (3)	C36—C35	1.382 (4)
C24—C25	1.389 (3)	C36—H36	0.9300
C24—C23	1.403 (3)	C33—C34	1.367 (5)
C24—C27	1.458 (3)	C33—H33	0.9300
C22—C23	1.377 (3)	C34—C35	1.381 (5)
C22—C21	1.407 (3)	C22A—H22A	0.9600
C11—C16	1.396 (3)	C22A—H22B	0.9600
C11—C12	1.409 (4)	C22A—H22C	0.9600
C11—C17	1.499 (4)	C35—H35	0.9300
C26—C21	1.379 (4)	C12A—H12A	0.9600
C26—C25	1.392 (4)	C12A—H12B	0.9600
C26—H26	0.9300	C12A—H12C	0.9600
C25—H25	0.9300	O1—H1A	0.8532
C12—C13	1.390 (4)	O1—H1B	0.8547
C23—H23	0.9300	O2—H2A	0.8539
C27—H27	0.9300	O2—H2B	0.8485
C13—C14	1.380 (4)

C27—N27—N17	114.0 (2)	C15—C16—H16	119.1
C17—N17—N27	121.1 (2)	C11—C16—H16	119.1
C17—N17—H17	119.5	C15—C14—C13	120.3 (3)
N27—N17—H17	119.5	C15—C14—H14	119.9
C21—O21—C37	117.1 (2)	C13—C14—H14	119.9
C22—O22—C22A	117.1 (2)	O21—C37—C31	112.3 (2)
C12—O12—C12A	119.8 (2)	O21—C37—H37A	109.1
C25—C24—C23	118.9 (2)	C31—C37—H37A	109.1
C25—C24—C27	118.9 (2)	O21—C37—H37B	109.1
C23—C24—C27	122.1 (2)	C31—C37—H37B	109.1
O22—C22—C23	125.1 (2)	H37A—C37—H37B	107.9
O22—C22—C21	115.0 (2)	C14—C15—C16	119.8 (3)
C23—C22—C21	119.9 (2)	C14—C15—H15	120.1
C16—C11—C12	117.5 (2)	C16—C15—H15	120.1
C16—C11—C17	116.1 (2)	C33—C32—C31	122.8 (3)
C12—C11—C17	126.4 (2)	C33—C32—Cl1	118.0 (2)
C21—C26—C25	120.4 (2)	C31—C32—Cl1	119.2 (2)
C21—C26—H26	119.8	C35—C36—C31	121.8 (3)
C25—C26—H26	119.8	C35—C36—H36	119.1
C24—C25—C26	120.5 (2)	C31—C36—H36	119.1
C24—C25—H25	119.8	C34—C33—C32	118.2 (3)
C26—C25—H25	119.8	C34—C33—H33	120.9
O17—C17—N17	121.8 (2)	C32—C33—H33	120.9
O17—C17—C11	121.2 (2)	C33—C34—C35	121.4 (3)
N17—C17—C11	117.1 (2)	C33—C34—Cl2	119.3 (3)
O21—C21—C26	125.3 (2)	C35—C34—Cl2	119.3 (3)
O21—C21—C22	115.1 (2)	O22—C22A—H22A	109.5
C26—C21—C22	119.5 (2)	O22—C22A—H22B	109.5
O12—C12—C13	122.3 (2)	H22A—C22A—H22B	109.5
O12—C12—C11	117.6 (2)	O22—C22A—H22C	109.5
C13—C12—C11	120.0 (2)	H22A—C22A—H22C	109.5
C22—C23—C24	120.7 (2)	H22B—C22A—H22C	109.5
C22—C23—H23	119.7	C34—C35—C36	119.1 (3)
C24—C23—H23	119.7	C34—C35—H35	120.5
N27—C27—C24	122.2 (2)	C36—C35—H35	120.5
N27—C27—H27	118.9	O12—C12A—H12A	109.5
C24—C27—H27	118.9	O12—C12A—H12B	109.5
C14—C13—C12	120.6 (3)	H12A—C12A—H12B	109.5
C14—C13—H13	119.7	O12—C12A—H12C	109.5
C12—C13—H13	119.7	H12A—C12A—H12C	109.5
C36—C31—C32	116.7 (3)	H12B—C12A—H12C	109.5
C36—C31—C37	121.6 (3)	H1A—O1—H1B	115.6
C32—C31—C37	121.8 (3)	H2A—O2—H2B	116.3
C15—C16—C11	121.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O17ⁱ	0.85	2.02	2.852 (3)	164
O2—H2A···O1ⁱⁱ	0.85	2.10	2.918 (6)	161
O2—H2B···O1ⁱⁱⁱ	0.85	1.89	2.711 (6)	162
O1—H1A···O17	0.85	2.19	2.987 (3)	155
O1—H1A···N27	0.85	2.54	3.180 (3)	133
N17—H17···O12	0.86	1.93	2.625 (3)	137

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀Cl₂N₂O₄·1.5H₂O
M_r	486.34
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.7689 (16), 8.3390 (17), 18.345 (4)
α, β, γ (°)	80.93 (3), 77.85 (3), 86.50 (3)
V (Å³)	1146.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.902, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	5880, 4015, 2630
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.130, 1.02
No. of reflections	4015
No. of parameters	295
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.33

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 1997b).