(4-Chloro­benzohydrazidato-κ2N′,O)[2-(4-chloro­benzoyl­hydrazinyl­idene-κ2N1,O)-3-phenyl­propionato(2−)-κO1]oxidovanadium(V) methanol monosolvate

Wong, H.W.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810045678

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1558

https://doi.org/10.1107/S1600536810045678

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(4-Chlorobenzohydrazidato-κ²N′,O)[2-(4-chlorobenzoylhydrazinylidene-κ²N¹,O)-3-phenylpropionato(2−)-κO¹]oxidovanadium(V) methanol monosolvate

Hon Wee Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 November 2010; accepted 7 November 2010; online 13 November 2010)

The V^V atom in the title compound, [V(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)O]·CH₃OH, is N,O-chelated by the benzoylhydrazidate anion and O,N,O′-chelated by the (benzoylhydrazinylidene)propionate dianion. The distorted octahedral trans-N₂O₄ coordination geometry is completed by the vanadyl O atom. The mononuclear and solvent molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds about a center of inversion, generating a dimer.

Related literature

For (benzohydrazidato)[2-(benzoylhydrazinylidene)propionato)(2–)]oxidovanadium(V), see: Wong et al. (2009a ,b ).

Experimental

Crystal data

[V(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)O]·CH₄O
M_r = 583.29
Triclinic, $[P \overline 1]$
a = 8.3217 (4) Å
b = 11.2505 (6) Å
c = 15.5064 (8) Å
α = 109.4045 (7)°
β = 98.8890 (7)°
γ = 111.6936 (7)°
V = 1206.93 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.821, T_max = 0.935
15037 measured reflections
5517 independent reflections
4907 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.116
S = 1.03
5517 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88	1.98	2.741 (2)	143
N4—H4⋯O6ⁱ	0.88	1.94	2.792 (3)	162
O6—H6⋯O2	0.84	2.27	2.908 (3)	133
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045678/hg2740sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045678/hg2740Isup2.hkl

checkCIF report

Comment top

The reaction of vanadyl(IV) sulfate and the Schiff base that is synthesized by condensing a substituted benzhydrazine and a substituted pyruvic acid leads a vanadium(V) derivative of the Schiff base. However, another mole of the Schiff base is cleaved and the resulting benzhydrazine monoanion also chelates to the metal atom (Wong et al., 2009a, 2009b). A similar product is isolated in the present study on the reaction of the Schiff base, 2-[4-chlorobenzoylhydrazono]-3-phenylpropionic acid so that the metal atom is chelated by two different ligands. The mononuclear mixed-ligand compound crystallizes as a monosolvate (Scheme I, Fig. 1). The vanadium(V) atom is N,O-chelated by the benzoylhydrazidate anion and O,N,O'-chelated by the (benzoylhydrazinylidene)propionate dianion; the terdentate chelate binds in a meridional mode. The octahedral trans-N₂O₄ coordination geometry is completed by the vanadyl O atom. The mononuclear and solvent molecules are linked by hydrogen bonds about a center-of-inversion to generate a hydrogen-bonded dimer.

Related literature top

For (benzohydrazidato)[2-(benzoylhydrazinylidene)propionato)(2–)]oxidovanadium(V), see: Wong et al. (2009a,b).

Experimental top

2-[4-Chlorobenzoylhydrazono]-3-phenylpropionic acid prepared from the condensation reaction of 4-chlorobenzhydrazide and 3-phenylpyruvic acid. The compound (1.00 g, 3 mmol) and vanadyl sulfate (1.25 g, 1.5 mmol) in 50 ml of methanol for 5 h. Slow evaporation of the filtrate gave brownish orange crystals.

Structure description top

For (benzohydrazidato)[2-(benzoylhydrazinylidene)propionato)(2–)]oxidovanadium(V), see: Wong et al. (2009a,b).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of VO(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)^.CH₃OH at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(4-Chlorobenzohydrazidato-κ²N',O)[2-(4- chlorobenzoylhydrazinylidene-κ²N¹,O)- 3-phenylpropionato(2-)-κO¹]oxidovanadium(V) methanol monosolvate top

Crystal data top

[V(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)O]·CH₄O	Z = 2
M_r = 583.29	F(000) = 596
Triclinic, P1	D_x = 1.605 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3217 (4) Å	Cell parameters from 8039 reflections
b = 11.2505 (6) Å	θ = 2.6–28.3°
c = 15.5064 (8) Å	µ = 0.68 mm⁻¹
α = 109.4045 (7)°	T = 100 K
β = 98.8890 (7)°	Block, brown
γ = 111.6936 (7)°	0.30 × 0.20 × 0.10 mm
V = 1206.93 (11) Å³

Data collection top

Bruker SMART APEX diffractometer	5517 independent reflections
Radiation source: fine-focus sealed tube	4907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.821, T_max = 0.935	k = −14→14
15037 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0658P)² + 1.2158P] where P = (F_o² + 2F_c²)/3
5517 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

[V(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)O]·CH₄O	γ = 111.6936 (7)°
M_r = 583.29	V = 1206.93 (11) Å³
Triclinic, P1	Z = 2
a = 8.3217 (4) Å	Mo Kα radiation
b = 11.2505 (6) Å	µ = 0.68 mm⁻¹
c = 15.5064 (8) Å	T = 100 K
α = 109.4045 (7)°	0.30 × 0.20 × 0.10 mm
β = 98.8890 (7)°

Data collection top

Bruker SMART APEX diffractometer	5517 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4907 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.935	R_int = 0.021
15037 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	Δρ_max = 0.54 e Å⁻³
5517 reflections	Δρ_min = −0.85 e Å⁻³
335 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
V1	0.70290 (4)	0.70483 (4)	0.70065 (2)	0.01467 (10)
Cl1	1.70732 (7)	1.31564 (6)	1.15657 (4)	0.02577 (14)
Cl2	0.91329 (8)	0.00311 (6)	0.37080 (4)	0.02773 (14)
O1	0.47185 (19)	0.53272 (15)	0.66919 (10)	0.0174 (3)
O2	0.3293 (2)	0.35991 (16)	0.71185 (11)	0.0225 (3)
O3	0.95256 (19)	0.84331 (15)	0.78583 (10)	0.0179 (3)
O4	0.8120 (2)	0.54984 (16)	0.65625 (10)	0.0185 (3)
O5	0.6190 (2)	0.81279 (16)	0.70892 (11)	0.0204 (3)
O6	0.4172 (3)	0.2179 (3)	0.54539 (15)	0.0477 (5)
H6	0.3470	0.2073	0.5787	0.072*
N1	0.7353 (2)	0.66447 (18)	0.82203 (12)	0.0151 (3)
N2	0.8951 (2)	0.75265 (18)	0.89745 (12)	0.0167 (3)
N3	0.7294 (2)	0.56220 (19)	0.51836 (12)	0.0174 (3)
H3	0.7125	0.5358	0.4562	0.021*
N4	0.6962 (2)	0.66803 (18)	0.57236 (12)	0.0174 (3)
H4	0.6710	0.7206	0.5467	0.021*
C1	0.4566 (3)	0.4711 (2)	0.72789 (14)	0.0171 (4)
C2	0.6167 (3)	0.5496 (2)	0.81905 (14)	0.0162 (4)
C3	0.6358 (3)	0.4883 (2)	0.88969 (15)	0.0193 (4)
H3A	0.5156	0.4400	0.8968	0.023*
H3B	0.7195	0.5644	0.9535	0.023*
C4	0.7112 (3)	0.3833 (2)	0.85310 (15)	0.0196 (4)
C5	0.8986 (3)	0.4305 (3)	0.87107 (18)	0.0266 (5)
H5	0.9795	0.5281	0.9077	0.032*
C6	0.9674 (4)	0.3354 (3)	0.8356 (2)	0.0347 (6)
H6A	1.0952	0.3683	0.8482	0.042*
C7	0.8502 (4)	0.1930 (3)	0.7821 (2)	0.0364 (6)
H7	0.8976	0.1281	0.7587	0.044*
C8	0.6639 (4)	0.1455 (3)	0.76274 (19)	0.0333 (6)
H8	0.5833	0.0479	0.7255	0.040*
C9	0.5945 (3)	0.2402 (2)	0.79772 (17)	0.0262 (5)
H9	0.4665	0.2071	0.7838	0.031*
C10	0.9974 (3)	0.8461 (2)	0.87082 (14)	0.0162 (4)
C11	1.1731 (3)	0.9611 (2)	0.94136 (14)	0.0172 (4)
C12	1.2677 (3)	1.0766 (2)	0.92264 (15)	0.0202 (4)
H12	1.2197	1.0797	0.8642	0.024*
C13	1.4313 (3)	1.1865 (2)	0.98931 (16)	0.0216 (4)
H13	1.4952	1.2659	0.9774	0.026*
C14	1.4999 (3)	1.1790 (2)	1.07313 (15)	0.0196 (4)
C15	1.4091 (3)	1.0649 (2)	1.09321 (15)	0.0200 (4)
H15	1.4592	1.0613	1.1511	0.024*
C16	1.2445 (3)	0.9567 (2)	1.02717 (15)	0.0184 (4)
H16	1.1795	0.8789	1.0403	0.022*
C17	0.7901 (3)	0.5014 (2)	0.56797 (14)	0.0172 (4)
C18	0.8251 (3)	0.3815 (2)	0.51698 (15)	0.0173 (4)
C19	0.8981 (3)	0.3266 (3)	0.57203 (16)	0.0249 (5)
H19	0.9271	0.3685	0.6402	0.030*
C20	0.9286 (3)	0.2114 (3)	0.52785 (17)	0.0272 (5)
H20	0.9789	0.1740	0.5651	0.033*
C21	0.8842 (3)	0.1515 (2)	0.42783 (16)	0.0209 (4)
C22	0.8150 (3)	0.2059 (2)	0.37210 (15)	0.0187 (4)
H22	0.7878	0.1646	0.3041	0.022*
C23	0.7861 (3)	0.3220 (2)	0.41712 (14)	0.0173 (4)
H23	0.7395	0.3610	0.3798	0.021*
C24	0.4283 (7)	0.1015 (6)	0.5053 (4)	0.0873 (15)
H24A	0.4884	0.1067	0.4561	0.131*
H24B	0.3056	0.0221	0.4750	0.131*
H24C	0.4994	0.0876	0.5543	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.01538 (17)	0.01633 (18)	0.01099 (17)	0.00714 (14)	0.00334 (13)	0.00470 (13)
Cl1	0.0165 (2)	0.0231 (3)	0.0221 (3)	0.0044 (2)	0.0027 (2)	−0.0014 (2)
Cl2	0.0365 (3)	0.0239 (3)	0.0284 (3)	0.0188 (2)	0.0127 (2)	0.0106 (2)
O1	0.0156 (7)	0.0198 (7)	0.0140 (7)	0.0066 (6)	0.0026 (5)	0.0064 (6)
O2	0.0191 (7)	0.0212 (8)	0.0198 (7)	0.0039 (6)	0.0034 (6)	0.0075 (6)
O3	0.0175 (7)	0.0187 (7)	0.0119 (7)	0.0051 (6)	0.0024 (5)	0.0047 (6)
O4	0.0186 (7)	0.0222 (7)	0.0132 (7)	0.0093 (6)	0.0047 (5)	0.0057 (6)
O5	0.0229 (7)	0.0216 (7)	0.0164 (7)	0.0115 (6)	0.0054 (6)	0.0066 (6)
O6	0.0594 (14)	0.0624 (15)	0.0313 (11)	0.0334 (12)	0.0211 (10)	0.0214 (10)
N1	0.0156 (8)	0.0170 (8)	0.0116 (7)	0.0085 (7)	0.0040 (6)	0.0037 (6)
N2	0.0138 (8)	0.0178 (8)	0.0130 (8)	0.0056 (7)	0.0013 (6)	0.0034 (7)
N3	0.0173 (8)	0.0209 (9)	0.0112 (8)	0.0079 (7)	0.0047 (6)	0.0042 (7)
N4	0.0170 (8)	0.0188 (8)	0.0148 (8)	0.0075 (7)	0.0047 (6)	0.0063 (7)
C1	0.0172 (9)	0.0187 (10)	0.0142 (9)	0.0092 (8)	0.0048 (8)	0.0044 (8)
C2	0.0159 (9)	0.0184 (9)	0.0137 (9)	0.0085 (8)	0.0063 (7)	0.0045 (8)
C3	0.0210 (10)	0.0203 (10)	0.0154 (9)	0.0075 (8)	0.0057 (8)	0.0081 (8)
C4	0.0232 (10)	0.0211 (10)	0.0157 (9)	0.0089 (9)	0.0059 (8)	0.0105 (8)
C5	0.0253 (11)	0.0285 (12)	0.0272 (12)	0.0122 (10)	0.0077 (9)	0.0132 (10)
C6	0.0341 (13)	0.0444 (15)	0.0382 (14)	0.0254 (12)	0.0152 (11)	0.0214 (12)
C7	0.0557 (17)	0.0392 (14)	0.0356 (14)	0.0350 (14)	0.0235 (13)	0.0205 (12)
C8	0.0507 (16)	0.0233 (12)	0.0286 (12)	0.0176 (11)	0.0123 (11)	0.0132 (10)
C9	0.0300 (12)	0.0226 (11)	0.0254 (11)	0.0093 (10)	0.0073 (9)	0.0132 (9)
C10	0.0178 (9)	0.0186 (9)	0.0135 (9)	0.0112 (8)	0.0050 (7)	0.0050 (8)
C11	0.0166 (9)	0.0185 (10)	0.0157 (9)	0.0096 (8)	0.0055 (8)	0.0042 (8)
C12	0.0222 (10)	0.0216 (10)	0.0167 (10)	0.0103 (9)	0.0068 (8)	0.0073 (8)
C13	0.0204 (10)	0.0189 (10)	0.0223 (11)	0.0071 (8)	0.0092 (8)	0.0061 (8)
C14	0.0147 (9)	0.0200 (10)	0.0156 (9)	0.0066 (8)	0.0041 (8)	−0.0004 (8)
C15	0.0189 (10)	0.0240 (11)	0.0137 (9)	0.0111 (9)	0.0046 (8)	0.0028 (8)
C16	0.0180 (9)	0.0184 (10)	0.0162 (9)	0.0076 (8)	0.0057 (8)	0.0048 (8)
C17	0.0126 (9)	0.0200 (10)	0.0147 (9)	0.0054 (8)	0.0041 (7)	0.0049 (8)
C18	0.0140 (9)	0.0180 (9)	0.0158 (9)	0.0055 (8)	0.0045 (7)	0.0044 (8)
C19	0.0316 (12)	0.0299 (12)	0.0154 (10)	0.0175 (10)	0.0070 (9)	0.0084 (9)
C20	0.0339 (12)	0.0318 (12)	0.0249 (11)	0.0210 (11)	0.0098 (10)	0.0151 (10)
C21	0.0196 (10)	0.0180 (10)	0.0234 (11)	0.0083 (8)	0.0076 (8)	0.0067 (8)
C22	0.0150 (9)	0.0197 (10)	0.0166 (9)	0.0057 (8)	0.0043 (7)	0.0052 (8)
C23	0.0131 (9)	0.0191 (10)	0.0153 (9)	0.0052 (8)	0.0024 (7)	0.0054 (8)
C24	0.076 (3)	0.099 (4)	0.109 (4)	0.038 (3)	0.040 (3)	0.068 (3)

Geometric parameters (Å, º) top

V1—O5	1.5905 (15)	C6—H6A	0.9500
V1—N4	1.8797 (17)	C7—C8	1.385 (4)
V1—O3	1.9697 (15)	C7—H7	0.9500
V1—O1	2.0036 (15)	C8—C9	1.389 (4)
V1—N1	2.0791 (17)	C8—H8	0.9500
V1—O4	2.2149 (15)	C9—H9	0.9500
Cl1—C14	1.744 (2)	C10—C11	1.474 (3)
Cl2—C21	1.736 (2)	C11—C16	1.395 (3)
O1—C1	1.310 (3)	C11—C12	1.399 (3)
O2—C1	1.217 (3)	C12—C13	1.387 (3)
O3—C10	1.299 (2)	C12—H12	0.9500
O4—C17	1.248 (2)	C13—C14	1.379 (3)
O6—C24	1.295 (6)	C13—H13	0.9500
O6—H6	0.8400	C14—C15	1.392 (3)
N1—C2	1.284 (3)	C15—C16	1.383 (3)
N1—N2	1.376 (2)	C15—H15	0.9500
N2—C10	1.318 (3)	C16—H16	0.9500
N3—C17	1.342 (3)	C17—C18	1.478 (3)
N3—N4	1.359 (2)	C18—C19	1.395 (3)
N3—H3	0.8800	C18—C23	1.395 (3)
N4—H4	0.8800	C19—C20	1.386 (3)
C1—C2	1.507 (3)	C19—H19	0.9500
C2—C3	1.493 (3)	C20—C21	1.393 (3)
C3—C4	1.525 (3)	C20—H20	0.9500
C3—H3A	0.9900	C21—C22	1.382 (3)
C3—H3B	0.9900	C22—C23	1.389 (3)
C4—C9	1.393 (3)	C22—H22	0.9500
C4—C5	1.395 (3)	C23—H23	0.9500
C5—C6	1.391 (4)	C24—H24A	0.9800
C5—H5	0.9500	C24—H24B	0.9800
C6—C7	1.385 (4)	C24—H24C	0.9800

O5—V1—N4	93.72 (8)	C7—C8—H8	119.9
O5—V1—O3	97.65 (7)	C9—C8—H8	119.9
N4—V1—O3	108.53 (7)	C8—C9—C4	120.5 (2)
O5—V1—O1	98.01 (7)	C8—C9—H9	119.7
N4—V1—O1	96.05 (7)	C4—C9—H9	119.7
O3—V1—O1	149.78 (6)	O3—C10—N2	123.85 (18)
O5—V1—N1	112.76 (7)	O3—C10—C11	117.81 (18)
N4—V1—N1	152.97 (7)	N2—C10—C11	118.34 (18)
O3—V1—N1	74.45 (6)	C16—C11—C12	119.72 (19)
O1—V1—N1	75.69 (6)	C16—C11—C10	120.61 (19)
O5—V1—O4	167.39 (7)	C12—C11—C10	119.66 (19)
N4—V1—O4	73.68 (7)	C13—C12—C11	120.1 (2)
O3—V1—O4	86.92 (6)	C13—C12—H12	119.9
O1—V1—O4	83.33 (6)	C11—C12—H12	119.9
N1—V1—O4	79.76 (6)	C14—C13—C12	119.0 (2)
C1—O1—V1	119.51 (13)	C14—C13—H13	120.5
C10—O3—V1	116.22 (13)	C12—C13—H13	120.5
C17—O4—V1	112.25 (13)	C13—C14—C15	121.97 (19)
C24—O6—H6	109.5	C13—C14—Cl1	119.34 (17)
C2—N1—N2	122.37 (17)	C15—C14—Cl1	118.69 (16)
C2—N1—V1	118.81 (14)	C16—C15—C14	118.7 (2)
N2—N1—V1	118.25 (13)	C16—C15—H15	120.7
C10—N2—N1	106.72 (16)	C14—C15—H15	120.7
C17—N3—N4	114.23 (16)	C15—C16—C11	120.4 (2)
C17—N3—H3	122.9	C15—C16—H16	119.8
N4—N3—H3	122.9	C11—C16—H16	119.8
N3—N4—V1	121.55 (14)	O4—C17—N3	117.01 (19)
N3—N4—H4	119.2	O4—C17—C18	123.37 (19)
V1—N4—H4	119.2	N3—C17—C18	119.62 (18)
O2—C1—O1	124.82 (19)	C19—C18—C23	119.9 (2)
O2—C1—C2	121.66 (19)	C19—C18—C17	117.78 (19)
O1—C1—C2	113.50 (18)	C23—C18—C17	122.34 (19)
N1—C2—C3	126.31 (18)	C20—C19—C18	120.3 (2)
N1—C2—C1	111.75 (18)	C20—C19—H19	119.8
C3—C2—C1	121.66 (18)	C18—C19—H19	119.8
C2—C3—C4	108.71 (16)	C19—C20—C21	118.8 (2)
C2—C3—H3A	109.9	C19—C20—H20	120.6
C4—C3—H3A	109.9	C21—C20—H20	120.6
C2—C3—H3B	109.9	C22—C21—C20	121.8 (2)
C4—C3—H3B	109.9	C22—C21—Cl2	118.73 (17)
H3A—C3—H3B	108.3	C20—C21—Cl2	119.44 (17)
C9—C4—C5	118.9 (2)	C21—C22—C23	118.96 (19)
C9—C4—C3	120.8 (2)	C21—C22—H22	120.5
C5—C4—C3	120.2 (2)	C23—C22—H22	120.5
C6—C5—C4	120.4 (2)	C22—C23—C18	120.22 (19)
C6—C5—H5	119.8	C22—C23—H23	119.9
C4—C5—H5	119.8	C18—C23—H23	119.9
C7—C6—C5	120.1 (2)	O6—C24—H24A	109.5
C7—C6—H6A	119.9	O6—C24—H24B	109.5
C5—C6—H6A	119.9	H24A—C24—H24B	109.5
C8—C7—C6	119.9 (2)	O6—C24—H24C	109.5
C8—C7—H7	120.0	H24A—C24—H24C	109.5
C6—C7—H7	120.0	H24B—C24—H24C	109.5
C7—C8—C9	120.1 (2)

O5—V1—O1—C1	−118.37 (15)	C2—C3—C4—C5	83.8 (2)
N4—V1—O1—C1	147.00 (15)	C9—C4—C5—C6	−1.2 (3)
O3—V1—O1—C1	2.2 (2)	C3—C4—C5—C6	−178.3 (2)
N1—V1—O1—C1	−6.82 (14)	C4—C5—C6—C7	0.0 (4)
O4—V1—O1—C1	74.27 (14)	C5—C6—C7—C8	0.9 (4)
O5—V1—O3—C10	105.44 (15)	C6—C7—C8—C9	−0.6 (4)
N4—V1—O3—C10	−158.01 (14)	C7—C8—C9—C4	−0.5 (4)
O1—V1—O3—C10	−15.2 (2)	C5—C4—C9—C8	1.4 (3)
N1—V1—O3—C10	−6.14 (14)	C3—C4—C9—C8	178.5 (2)
O4—V1—O3—C10	−86.36 (14)	V1—O3—C10—N2	8.3 (3)
O5—V1—O4—C17	−8.3 (4)	V1—O3—C10—C11	−171.56 (13)
N4—V1—O4—C17	−9.75 (14)	N1—N2—C10—O3	−4.2 (3)
O3—V1—O4—C17	−120.08 (14)	N1—N2—C10—C11	175.61 (16)
O1—V1—O4—C17	88.58 (14)	O3—C10—C11—C16	−168.54 (18)
N1—V1—O4—C17	165.18 (15)	N2—C10—C11—C16	11.6 (3)
O5—V1—N1—C2	100.74 (16)	O3—C10—C11—C12	12.4 (3)
N4—V1—N1—C2	−67.0 (2)	N2—C10—C11—C12	−167.50 (19)
O3—V1—N1—C2	−167.36 (16)	C16—C11—C12—C13	−0.3 (3)
O1—V1—N1—C2	7.94 (15)	C10—C11—C12—C13	178.82 (18)
O4—V1—N1—C2	−77.72 (15)	C11—C12—C13—C14	0.9 (3)
O5—V1—N1—N2	−87.67 (15)	C12—C13—C14—C15	−0.5 (3)
N4—V1—N1—N2	104.63 (19)	C12—C13—C14—Cl1	179.08 (16)
O3—V1—N1—N2	4.23 (13)	C13—C14—C15—C16	−0.6 (3)
O1—V1—N1—N2	179.52 (14)	Cl1—C14—C15—C16	179.84 (16)
O4—V1—N1—N2	93.86 (14)	C14—C15—C16—C11	1.2 (3)
C2—N1—N2—C10	169.75 (18)	C12—C11—C16—C15	−0.8 (3)
V1—N1—N2—C10	−1.5 (2)	C10—C11—C16—C15	−179.91 (18)
C17—N3—N4—V1	−8.5 (2)	V1—O4—C17—N3	8.5 (2)
O5—V1—N4—N3	−170.15 (15)	V1—O4—C17—C18	−170.65 (15)
O3—V1—N4—N3	90.49 (15)	N4—N3—C17—O4	−1.4 (3)
O1—V1—N4—N3	−71.68 (15)	N4—N3—C17—C18	177.84 (17)
N1—V1—N4—N3	−1.5 (3)	O4—C17—C18—C19	−4.5 (3)
O4—V1—N4—N3	9.53 (14)	N3—C17—C18—C19	176.35 (19)
V1—O1—C1—O2	−173.47 (16)	O4—C17—C18—C23	174.85 (19)
V1—O1—C1—C2	5.1 (2)	N3—C17—C18—C23	−4.3 (3)
N2—N1—C2—C3	−4.7 (3)	C23—C18—C19—C20	−1.3 (3)
V1—N1—C2—C3	166.52 (16)	C17—C18—C19—C20	178.0 (2)
N2—N1—C2—C1	−178.68 (16)	C18—C19—C20—C21	−0.3 (4)
V1—N1—C2—C1	−7.5 (2)	C19—C20—C21—C22	1.6 (4)
O2—C1—C2—N1	−179.70 (19)	C19—C20—C21—Cl2	−177.59 (19)
O1—C1—C2—N1	1.7 (2)	C20—C21—C22—C23	−1.2 (3)
O2—C1—C2—C3	6.0 (3)	Cl2—C21—C22—C23	178.00 (15)
O1—C1—C2—C3	−172.65 (18)	C21—C22—C23—C18	−0.5 (3)
N1—C2—C3—C4	−93.3 (2)	C19—C18—C23—C22	1.8 (3)
C1—C2—C3—C4	80.1 (2)	C17—C18—C23—C22	−177.57 (18)
C2—C3—C4—C9	−93.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.98	2.741 (2)	143
N4—H4···O6ⁱ	0.88	1.94	2.792 (3)	162
O6—H6···O2	0.84	2.27	2.908 (3)	133

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[V(C₇H₆ClN₂O)(C₁₆H₁₁ClN₂O₃)O]·CH₄O
M_r	583.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.3217 (4), 11.2505 (6), 15.5064 (8)
α, β, γ (°)	109.4045 (7), 98.8890 (7), 111.6936 (7)
V (Å³)	1206.93 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.821, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	15037, 5517, 4907
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.116, 1.03
No. of reflections	5517
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.85

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.98	2.741 (2)	143
N4—H4···O6ⁱ	0.88	1.94	2.792 (3)	162
O6—H6···O2	0.84	2.27	2.908 (3)	133

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009a). Acta Cryst. E65, m422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009b). Acta Cryst. E65, m718. Web of Science CSD CrossRef IUCr Journals Google Scholar

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