Aqua­chloridobis(2-eth­oxy-6-formyl­phenolato-κ2O1,O6)chromium(III) acetonitrile hemisolvate

Ghelenji, S.; Kargar, H.; Sharafi, Z.; Kia, R.

doi:10.1107/S1600536811037275

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1393

https://doi.org/10.1107/S1600536811037275

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Aquachloridobis(2-ethoxy-6-formylphenolato-κ²O¹,O⁶)chromium(III) acetonitrile hemisolvate

Safoora Ghelenji,^a Hadi Kargar,^b ^* Zahra Sharafi ^c and Reza Kia ^d,^e

^aDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, ^bChemistry Department, Payame Noor University, Tehran 19395-4697, I. R. of Iran, ^cDepartment of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran, ^dX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^eDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: hkargar@pnu.ac.ir

(Received 28 August 2011; accepted 13 September 2011; online 17 September 2011)

In the mononuclear complex molecule of the title compound, [Cr(C₉H₉O₃)₂Cl(H₂O)]·0.5CH₃CN, the Cr^III atom displays an elongated octahedral coordination geometry. The dihedral angle between the benzene rings is 12.27 (11)°. Adjacent complex molecules are linked into dimers by O—H⋯O hydrogen bonds, generating rings of R₁²(6) and R₁²(5) graph-set motifs, and by aromatic π–π stacking interactions, with a centroid–centroid distance of 3.812 (2) Å. The crystal packing is further stabilized by intermolecular C—H⋯N hydrogen bonds. The C and N atoms of the acetonitrile solvent molecule are located on a crystallographic twofold axis.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the structures of tetradentate Schiff bases synthesized by our group, see: Kargar et al. (2009 , 2010 ).

Experimental

Crystal data

[Cr(C₉H₉O₃)₂Cl(H₂O)]·0.5C₂H₃N
M_r = 456.32
Monoclinic, C 2/c
a = 19.292 (3) Å
b = 10.1211 (10) Å
c = 20.953 (3) Å
β = 91.824 (11)°
V = 4089.1 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 291 K
0.25 × 0.15 × 0.12 mm

Data collection

Stoe IPDS 2T Image Plate diffractometer
Absorption correction: multi-scan [MULABS (Blessing, 1995 ) in PLATON (Spek, 2009 )] T_min = 0.901, T_max = 1.000
9374 measured reflections
4371 independent reflections
2108 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.078
S = 0.80
4371 reflections
261 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1ⁱ	0.85	2.10	2.826 (3)	143
O1W—H1W1⋯O5ⁱ	0.85	2.28	3.007 (4)	144
O1W—H2W1⋯O3ⁱ	0.85	2.22	2.813 (3)	127
O1W—H2W1⋯O6ⁱ	0.85	2.14	2.940 (4)	158
C7—H7A⋯N1ⁱⁱ	0.93	2.62	3.171 (4)	119
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{5\over 2}}, -z]$ ; (ii) -x+1, -y+3, -z.

Data collection: X-AREA (Stoe & Cie, 2009 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037275/rz2636sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037275/rz2636Isup2.hkl

checkCIF report

Comment top

As part of our ongoing study of potential tetradenate Schiff bases (Kargar et al., 2009; Kargar et al. 2010) derived from different substituted salicylaldehydes, we have determined the crystal structure of the title compound, which was obtained by the reaction of chromium(III) chloride hexahydrate with 3-ethoxysalicylaldehyde in acetonitrile.

The asymmetric unit of the title compound, Fig. 1, comprises one mononuclear complex molecule and one half of an acetonitrile solvent molecule, whose C and N atoms are located on a crystallographic twofold axis. In the complex molecule, the metal atom displays an elongated octahedral coordination geometry. The dihedral angles between the substituted benzene rings is 12.27 (11)°. Strong intermolecular O—H···O hydrogen bonds (Table 1) link adjacent complex molecules into dimers, generating rings of R²₁(6) and R²₁(5) graph set motifs (Bernstein et al., 1995). In the dimers, aromatic π–π stacking interactions with centroid-to-centroid distance of 3.812 (2) Å are observed (Table 1). The crystal packing (Fig. 2) is further stabilized by C—H···N hydrogen bonds involving the acetonitrile molecule.

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the structures of potential tetradentate Schiff bases synthesized by our group, see: Kargar et al. (2009, 2010).

Experimental top

The title compound was synthesized by adding 3-ethoxy-salicylaldehyde (4 mmol) to a solution of CrCl₃. 6H₂O (2 mmol) in acetonitrile (50 ml). The mixture was refluxed with stirring for 3 h. The resultant dark-green solution was filtered and single crystals suitable for X-ray structure determination were grown from the solution by slow evaporation of the solvent at room temperature over several days.

Structure description top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the structures of potential tetradentate Schiff bases synthesized by our group, see: Kargar et al. (2009, 2010).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. The acetonitrile solvent is disordered about a crystallographic twofold rotation axis.
	Fig. 2. Crystal packing of the title compound viewed down the a axis. Intermolecular hydrogen interactions are shown as dashed lines. H atoms not involved in hydrogen bonding are omitted for clarity.

Aquachloridobis(2-ethoxy-6-formylphenolato- κ²O¹,O⁶)chromium(III) acetonitrile hemisolvate top

Crystal data top

[Cr(C₉H₉O₃)₂Cl(H₂O)]·0.5C₂H₃N	F(000) = 1888
M_r = 456.32	D_x = 1.482 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1749 reflections
a = 19.292 (3) Å	θ = 2.2–29.5°
b = 10.1211 (10) Å	µ = 0.73 mm⁻¹
c = 20.953 (3) Å	T = 291 K
β = 91.824 (11)°	Block, dark-green
V = 4089.1 (10) Å³	0.25 × 0.15 × 0.12 mm
Z = 8

Data collection top

Stoe IPDS 2T Image Plate diffractometer	4371 independent reflections
Radiation source: fine-focus sealed tube	2108 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ω scans	h = −24→24
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]	k = −11→12
T_min = 0.901, T_max = 1.000	l = −23→26
9374 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 0.80	w = 1/[σ²(F_o²) + (0.0193P)²] where P = (F_o² + 2F_c²)/3
4371 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cr(C₉H₉O₃)₂Cl(H₂O)]·0.5C₂H₃N	V = 4089.1 (10) Å³
M_r = 456.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.292 (3) Å	µ = 0.73 mm⁻¹
b = 10.1211 (10) Å	T = 291 K
c = 20.953 (3) Å	0.25 × 0.15 × 0.12 mm
β = 91.824 (11)°

Data collection top

Stoe IPDS 2T Image Plate diffractometer	4371 independent reflections
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]	2108 reflections with I > 2σ(I)
T_min = 0.901, T_max = 1.000	R_int = 0.070
9374 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 0.80	Δρ_max = 0.27 e Å⁻³
4371 reflections	Δρ_min = −0.33 e Å⁻³
261 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)
Cr1	0.64593 (2)	1.32691 (7)	0.04499 (3)	0.03258 (17)
Cl1	0.61724 (4)	1.48966 (12)	0.11688 (5)	0.0500 (3)
O1	0.72440 (10)	1.2660 (3)	0.09641 (12)	0.0352 (7)
O2	0.58449 (11)	1.2011 (3)	0.08794 (13)	0.0421 (8)
O3	0.70720 (10)	1.4377 (3)	−0.00154 (12)	0.0343 (7)
O4	0.56652 (10)	1.3822 (3)	−0.01146 (13)	0.0395 (7)
O5	0.84236 (11)	1.2384 (3)	0.15669 (13)	0.0506 (8)
O6	0.80992 (11)	1.5786 (3)	−0.04008 (14)	0.0460 (8)
C1	0.72533 (16)	1.1870 (4)	0.14529 (18)	0.0325 (9)
C2	0.78879 (17)	1.1670 (4)	0.18084 (19)	0.0386 (10)
C3	0.7924 (2)	1.0838 (5)	0.2312 (2)	0.0556 (13)
H3A	0.8347	1.0717	0.2528	0.067*
C4	0.7343 (2)	1.0156 (5)	0.2516 (2)	0.0632 (14)
H4A	0.7378	0.9601	0.2870	0.076*
C5	0.6731 (2)	1.0311 (5)	0.2196 (2)	0.0543 (13)
H5A	0.6345	0.9839	0.2323	0.065*
C6	0.66667 (19)	1.1183 (4)	0.16681 (19)	0.0385 (10)
C7	0.60077 (19)	1.1291 (4)	0.1337 (2)	0.0455 (12)
H7A	0.5658	1.0750	0.1485	0.055*
C8	0.90836 (18)	1.2297 (5)	0.1897 (2)	0.0581 (14)
H8A	0.9267	1.1407	0.1870	0.070*
H8B	0.9039	1.2522	0.2344	0.070*
C9	0.95559 (18)	1.3257 (6)	0.1581 (2)	0.0790 (17)
H9A	1.0012	1.3198	0.1775	0.118*
H9B	0.9381	1.4138	0.1630	0.118*
H9C	0.9576	1.3050	0.1135	0.118*
C10	0.69152 (17)	1.5300 (4)	−0.04271 (19)	0.0330 (10)
C11	0.74590 (19)	1.6113 (4)	−0.0648 (2)	0.0415 (11)
C12	0.7323 (2)	1.7116 (5)	−0.1067 (2)	0.0640 (15)
H12A	0.7684	1.7646	−0.1200	0.077*
C13	0.6644 (2)	1.7360 (5)	−0.1301 (2)	0.0764 (17)
H13A	0.6555	1.8044	−0.1589	0.092*
C14	0.6121 (2)	1.6586 (5)	−0.1102 (2)	0.0625 (14)
H14A	0.5671	1.6753	−0.1255	0.075*
C15	0.62361 (17)	1.5546 (4)	−0.06753 (19)	0.0381 (11)
C16	0.56650 (17)	1.4756 (5)	−0.04983 (19)	0.0400 (11)
H16A	0.5239	1.4965	−0.0693	0.048*
C17	0.86615 (18)	1.6679 (5)	−0.0508 (2)	0.0595 (13)
H17A	0.8541	1.7563	−0.0371	0.071*
H17B	0.8761	1.6707	−0.0958	0.071*
C18	0.92803 (19)	1.6186 (5)	−0.0130 (2)	0.0718 (17)
H18A	0.9666	1.6765	−0.0192	0.108*
H18B	0.9395	1.5312	−0.0269	0.108*
H18C	0.9176	1.6166	0.0315	0.108*
O1W	0.66200 (9)	1.1806 (3)	−0.01853 (11)	0.0375 (7)
H1W1	0.6804	1.1980	−0.0537	0.056*
H2W1	0.6804	1.1082	−0.0071	0.056*
N1	0.5000	1.8521 (9)	−0.2500	0.123 (3)
C19	0.5000	1.5944 (10)	−0.2500	0.137 (4)
H19A	0.5241	1.5628	−0.2864	0.206*	0.50
H19B	0.4531	1.5628	−0.2520	0.206*	0.50
H19C	0.5229	1.5628	−0.2116	0.206*	0.50
C20	0.5000	1.7396 (12)	−0.2500	0.076 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0213 (2)	0.0403 (4)	0.0361 (4)	−0.0020 (3)	−0.0004 (2)	0.0045 (4)
Cl1	0.0440 (5)	0.0546 (8)	0.0511 (7)	0.0016 (5)	−0.0026 (5)	−0.0124 (7)
O1	0.0267 (11)	0.0417 (18)	0.0369 (17)	−0.0002 (11)	−0.0029 (11)	0.0143 (15)
O2	0.0327 (13)	0.050 (2)	0.0435 (18)	−0.0103 (13)	0.0052 (13)	0.0062 (17)
O3	0.0236 (11)	0.0380 (18)	0.0412 (17)	0.0020 (11)	−0.0011 (11)	0.0118 (15)
O4	0.0241 (12)	0.052 (2)	0.0426 (18)	0.0052 (12)	−0.0045 (12)	0.0019 (16)
O5	0.0360 (13)	0.067 (2)	0.0477 (18)	0.0003 (13)	−0.0122 (13)	0.0142 (18)
O6	0.0334 (13)	0.0396 (18)	0.065 (2)	−0.0062 (12)	0.0060 (13)	0.0103 (17)
C1	0.0390 (18)	0.030 (3)	0.029 (2)	0.0044 (19)	0.0030 (17)	−0.005 (2)
C2	0.0449 (19)	0.038 (3)	0.033 (2)	0.007 (2)	−0.0006 (18)	0.003 (2)
C3	0.064 (3)	0.058 (3)	0.045 (3)	0.015 (2)	−0.001 (2)	0.009 (3)
C4	0.098 (4)	0.049 (3)	0.042 (3)	0.017 (3)	0.004 (3)	0.021 (3)
C5	0.071 (3)	0.042 (3)	0.050 (3)	−0.006 (2)	0.018 (2)	0.008 (3)
C6	0.050 (2)	0.037 (3)	0.029 (2)	−0.0024 (19)	0.008 (2)	−0.001 (2)
C7	0.047 (2)	0.044 (3)	0.047 (3)	−0.017 (2)	0.021 (2)	−0.003 (3)
C8	0.047 (2)	0.069 (4)	0.057 (3)	0.013 (2)	−0.018 (2)	−0.015 (3)
C9	0.043 (2)	0.113 (5)	0.080 (4)	−0.012 (3)	−0.011 (2)	0.000 (4)
C10	0.0368 (19)	0.029 (2)	0.033 (2)	0.0052 (17)	0.0041 (18)	−0.003 (2)
C11	0.048 (2)	0.032 (3)	0.044 (3)	−0.0016 (19)	0.005 (2)	0.004 (2)
C12	0.064 (3)	0.054 (4)	0.075 (4)	0.004 (2)	0.017 (3)	0.020 (3)
C13	0.083 (3)	0.065 (4)	0.081 (4)	0.015 (3)	0.003 (3)	0.047 (3)
C14	0.061 (3)	0.066 (4)	0.059 (3)	0.017 (3)	−0.011 (2)	0.015 (3)
C15	0.039 (2)	0.044 (3)	0.031 (2)	0.0149 (18)	−0.0003 (18)	0.009 (2)
C16	0.0324 (19)	0.056 (3)	0.031 (3)	0.013 (2)	−0.0046 (18)	−0.008 (3)
C17	0.055 (2)	0.041 (3)	0.084 (4)	−0.012 (2)	0.025 (2)	−0.007 (3)
C18	0.045 (2)	0.072 (4)	0.098 (4)	−0.022 (2)	0.006 (3)	−0.023 (3)
O1W	0.0300 (11)	0.0395 (17)	0.0432 (16)	0.0016 (12)	0.0049 (11)	0.0037 (16)
N1	0.144 (6)	0.099 (8)	0.129 (8)	0.000	0.057 (5)	0.000
C19	0.216 (11)	0.097 (10)	0.100 (9)	0.000	0.009 (7)	0.000
C20	0.078 (5)	0.107 (8)	0.043 (5)	0.000	0.023 (4)	0.000

Geometric parameters (Å, º) top

Cr1—O3	1.918 (2)	C9—H9A	0.9600
Cr1—O1	1.931 (2)	C9—H9B	0.9600
Cr1—O2	1.976 (3)	C9—H9C	0.9600
Cr1—O4	1.986 (3)	C10—C15	1.416 (5)
Cr1—O1W	2.021 (3)	C10—C11	1.422 (5)
Cr1—Cl1	2.3112 (13)	C11—C12	1.361 (6)
O1—C1	1.299 (4)	C12—C13	1.406 (6)
O2—C7	1.237 (5)	C12—H12A	0.9300
O3—C10	1.301 (4)	C13—C14	1.354 (6)
O4—C16	1.242 (4)	C13—H13A	0.9300
O5—C2	1.371 (4)	C14—C15	1.395 (6)
O5—C8	1.433 (4)	C14—H14A	0.9300
O6—C11	1.365 (4)	C15—C16	1.420 (5)
O6—C17	1.435 (4)	C16—H16A	0.9300
C1—C6	1.414 (5)	C17—C18	1.497 (6)
C1—C2	1.427 (5)	C17—H17A	0.9700
C2—C3	1.349 (5)	C17—H17B	0.9700
C3—C4	1.395 (5)	C18—H18A	0.9600
C3—H3A	0.9300	C18—H18B	0.9600
C4—C5	1.349 (6)	C18—H18C	0.9600
C4—H4A	0.9300	O1W—H1W1	0.8475
C5—C6	1.418 (6)	O1W—H2W1	0.8459
C5—H5A	0.9300	N1—C20	1.138 (11)
C6—C7	1.433 (5)	C19—C20	1.470 (12)
C7—H7A	0.9300	C19—H19A	0.9600
C8—C9	1.501 (6)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C8—H8B	0.9700

O3—Cr1—O1	89.17 (10)	C8—C9—H9B	109.5
O3—Cr1—O2	175.31 (12)	H9A—C9—H9B	109.5
O1—Cr1—O2	90.64 (11)	C8—C9—H9C	109.5
O3—Cr1—O4	90.51 (11)	H9A—C9—H9C	109.5
O1—Cr1—O4	176.86 (12)	H9B—C9—H9C	109.5
O2—Cr1—O4	89.43 (11)	O3—C10—C15	124.2 (3)
O3—Cr1—O1W	89.06 (10)	O3—C10—C11	118.2 (3)
O1—Cr1—O1W	89.98 (10)	C15—C10—C11	117.6 (4)
O2—Cr1—O1W	86.25 (10)	C12—C11—O6	125.4 (4)
O4—Cr1—O1W	86.89 (10)	C12—C11—C10	120.8 (4)
O3—Cr1—Cl1	94.52 (9)	O6—C11—C10	113.9 (4)
O1—Cr1—Cl1	93.64 (9)	C11—C12—C13	121.0 (4)
O2—Cr1—Cl1	90.16 (8)	C11—C12—H12A	119.5
O4—Cr1—Cl1	89.50 (8)	C13—C12—H12A	119.5
O1W—Cr1—Cl1	174.93 (6)	C14—C13—C12	119.1 (5)
C1—O1—Cr1	128.9 (2)	C14—C13—H13A	120.5
C7—O2—Cr1	126.3 (2)	C12—C13—H13A	120.5
C10—O3—Cr1	128.5 (2)	C13—C14—C15	121.9 (4)
C16—O4—Cr1	125.8 (2)	C13—C14—H14A	119.0
C2—O5—C8	117.3 (3)	C15—C14—H14A	119.0
C11—O6—C17	117.9 (3)	C14—C15—C10	119.7 (4)
O1—C1—C6	124.3 (3)	C14—C15—C16	118.9 (4)
O1—C1—C2	119.3 (3)	C10—C15—C16	121.5 (4)
C6—C1—C2	116.5 (4)	O4—C16—C15	127.9 (4)
C3—C2—O5	126.6 (4)	O4—C16—H16A	116.1
C3—C2—C1	121.2 (4)	C15—C16—H16A	116.1
O5—C2—C1	112.1 (3)	O6—C17—C18	107.5 (4)
C2—C3—C4	121.8 (4)	O6—C17—H17A	110.2
C2—C3—H3A	119.1	C18—C17—H17A	110.2
C4—C3—H3A	119.1	O6—C17—H17B	110.2
C5—C4—C3	119.3 (4)	C18—C17—H17B	110.2
C5—C4—H4A	120.4	H17A—C17—H17B	108.5
C3—C4—H4A	120.4	C17—C18—H18A	109.5
C4—C5—C6	120.9 (4)	C17—C18—H18B	109.5
C4—C5—H5A	119.6	H18A—C18—H18B	109.5
C6—C5—H5A	119.6	C17—C18—H18C	109.5
C1—C6—C5	120.3 (4)	H18A—C18—H18C	109.5
C1—C6—C7	121.0 (4)	H18B—C18—H18C	109.5
C5—C6—C7	118.6 (4)	Cr1—O1W—H1W1	119.9
O2—C7—C6	128.3 (4)	Cr1—O1W—H2W1	121.3
O2—C7—H7A	115.9	H1W1—O1W—H2W1	104.1
C6—C7—H7A	115.9	C20—C19—H19A	109.5
O5—C8—C9	106.8 (4)	C20—C19—H19B	109.5
O5—C8—H8A	110.4	H19A—C19—H19B	109.5
C9—C8—H8A	110.4	C20—C19—H19C	109.5
O5—C8—H8B	110.4	H19A—C19—H19C	109.5
C9—C8—H8B	110.4	H19B—C19—H19C	109.5
H8A—C8—H8B	108.6	N1—C20—C19	180.000 (5)
C8—C9—H9A	109.5

O3—Cr1—O1—C1	175.8 (3)	O1—C1—C6—C7	1.9 (6)
O2—Cr1—O1—C1	−8.9 (3)	C2—C1—C6—C7	−178.6 (4)
O1W—Cr1—O1—C1	−95.1 (3)	C4—C5—C6—C1	2.4 (6)
Cl1—Cr1—O1—C1	81.3 (3)	C4—C5—C6—C7	178.8 (4)
O1—Cr1—O2—C7	5.5 (3)	Cr1—O2—C7—C6	0.1 (6)
O4—Cr1—O2—C7	−177.6 (3)	C1—C6—C7—O2	−5.5 (6)
O1W—Cr1—O2—C7	95.5 (3)	C5—C6—C7—O2	178.2 (4)
Cl1—Cr1—O2—C7	−88.1 (3)	C2—O5—C8—C9	−174.6 (3)
O1—Cr1—O3—C10	−169.9 (3)	Cr1—O3—C10—C15	−8.8 (5)
O4—Cr1—O3—C10	13.2 (3)	Cr1—O3—C10—C11	171.7 (3)
O1W—Cr1—O3—C10	100.1 (3)	C17—O6—C11—C12	10.1 (6)
Cl1—Cr1—O3—C10	−76.3 (3)	C17—O6—C11—C10	−169.6 (3)
O3—Cr1—O4—C16	−12.4 (3)	O3—C10—C11—C12	−178.4 (4)
O2—Cr1—O4—C16	172.3 (3)	C15—C10—C11—C12	2.1 (6)
O1W—Cr1—O4—C16	−101.4 (3)	O3—C10—C11—O6	1.4 (5)
Cl1—Cr1—O4—C16	82.1 (3)	C15—C10—C11—O6	−178.1 (3)
Cr1—O1—C1—C6	6.6 (5)	O6—C11—C12—C13	179.1 (4)
Cr1—O1—C1—C2	−172.9 (3)	C10—C11—C12—C13	−1.2 (7)
C8—O5—C2—C3	−3.3 (6)	C11—C12—C13—C14	0.3 (8)
C8—O5—C2—C1	178.0 (3)	C12—C13—C14—C15	−0.5 (8)
O1—C1—C2—C3	−178.7 (4)	C13—C14—C15—C10	1.5 (7)
C6—C1—C2—C3	1.7 (6)	C13—C14—C15—C16	−178.6 (5)
O1—C1—C2—O5	0.0 (5)	O3—C10—C15—C14	178.2 (4)
C6—C1—C2—O5	−179.5 (3)	C11—C10—C15—C14	−2.3 (6)
O5—C2—C3—C4	−179.8 (4)	O3—C10—C15—C16	−1.6 (6)
C1—C2—C3—C4	−1.2 (7)	C11—C10—C15—C16	177.9 (4)
C2—C3—C4—C5	1.2 (7)	Cr1—O4—C16—C15	7.5 (6)
C3—C4—C5—C6	−1.8 (7)	C14—C15—C16—O4	−177.8 (4)
O1—C1—C6—C5	178.2 (4)	C10—C15—C16—O4	2.0 (6)
C2—C1—C6—C5	−2.3 (5)	C11—O6—C17—C18	173.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1ⁱ	0.85	2.10	2.826 (3)	143
O1W—H1W1···O5ⁱ	0.85	2.28	3.007 (4)	144
O1W—H2W1···O3ⁱ	0.85	2.22	2.813 (3)	127
O1W—H2W1···O6ⁱ	0.85	2.14	2.940 (4)	158
C7—H7A···N1ⁱⁱ	0.93	2.62	3.171 (4)	119
C19—H19A···Cl1ⁱⁱⁱ	0.96	2.80	3.745 (3)	167

Symmetry codes: (i) −x+3/2, −y+5/2, −z; (ii) −x+1, −y+3, −z; (iii) x, −y+3, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cr(C₉H₉O₃)₂Cl(H₂O)]·0.5C₂H₃N
M_r	456.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	19.292 (3), 10.1211 (10), 20.953 (3)
β (°)	91.824 (11)
V (Å³)	4089.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.25 × 0.15 × 0.12

Data collection
Diffractometer	Stoe IPDS 2T Image Plate
Absorption correction	Multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
T_min, T_max	0.901, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9374, 4371, 2108
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.078, 0.80
No. of reflections	4371
No. of parameters	261
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.33

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXTL (Sheldrick, 2008) PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1ⁱ	0.85	2.100	2.826 (3)	143.00
O1W—H1W1···O5ⁱ	0.85	2.280	3.007 (4)	144.00
O1W—H2W1···O3ⁱ	0.85	2.220	2.813 (3)	127.00
O1W—H2W1···O6ⁱ	0.85	2.140	2.940 (4)	158.00
C7—H7A···N1ⁱⁱ	0.93	2.62	3.171 (4)	119

Symmetry codes: (i) −x+3/2, −y+5/2, −z; (ii) −x+1, −y+3, −z.

Acknowledgements

HK thanks PNU for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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