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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1558.
Published online 2010 November 13. doi:  10.1107/S1600536810045678
PMCID: PMC3011505

(4-Chloro­benzohydrazidato-κ2 N′,O)[2-(4-chloro­benzoyl­hydrazinyl­idene-κ2 N 1,O)-3-phenyl­propionato(2−)-κO 1]oxidovanadium(V) methanol monosolvate

Abstract

The VV 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 [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1558-scheme1.jpg

Experimental

Crystal data

  • [V(C7H6ClN2O)(C16H11ClN2O3)O]·CH4O
  • M r = 583.29
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1558-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.116
  • S = 1.03
  • 5517 reflections
  • 335 parameters
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.85 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045678/hg2740Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

Carbon-, nitrogen- and oxygen-bound H-atoms were placed in calculated positions (C–H 0.95 to 0.99 Å, N–H 0.86 Å and O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Figures

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.

Crystal data

[V(C7H6ClN2O)(C16H11ClN2O3)O]·CH4OZ = 2
Mr = 583.29F(000) = 596
Triclinic, P1Dx = 1.605 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3217 (4) ÅCell parameters from 8039 reflections
b = 11.2505 (6) Åθ = 2.6–28.3°
c = 15.5064 (8) ŵ = 0.68 mm1
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

Bruker SMART APEX diffractometer5517 independent reflections
Radiation source: fine-focus sealed tube4907 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.821, Tmax = 0.935k = −14→14
15037 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0658P)2 + 1.2158P] where P = (Fo2 + 2Fc2)/3
5517 reflections(Δ/σ)max = 0.001
335 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = −0.85 e Å3

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

xyzUiso*/Ueq
V10.70290 (4)0.70483 (4)0.70065 (2)0.01467 (10)
Cl11.70732 (7)1.31564 (6)1.15657 (4)0.02577 (14)
Cl20.91329 (8)0.00311 (6)0.37080 (4)0.02773 (14)
O10.47185 (19)0.53272 (15)0.66919 (10)0.0174 (3)
O20.3293 (2)0.35991 (16)0.71185 (11)0.0225 (3)
O30.95256 (19)0.84331 (15)0.78583 (10)0.0179 (3)
O40.8120 (2)0.54984 (16)0.65625 (10)0.0185 (3)
O50.6190 (2)0.81279 (16)0.70892 (11)0.0204 (3)
O60.4172 (3)0.2179 (3)0.54539 (15)0.0477 (5)
H60.34700.20730.57870.072*
N10.7353 (2)0.66447 (18)0.82203 (12)0.0151 (3)
N20.8951 (2)0.75265 (18)0.89745 (12)0.0167 (3)
N30.7294 (2)0.56220 (19)0.51836 (12)0.0174 (3)
H30.71250.53580.45620.021*
N40.6962 (2)0.66803 (18)0.57236 (12)0.0174 (3)
H40.67100.72060.54670.021*
C10.4566 (3)0.4711 (2)0.72789 (14)0.0171 (4)
C20.6167 (3)0.5496 (2)0.81905 (14)0.0162 (4)
C30.6358 (3)0.4883 (2)0.88969 (15)0.0193 (4)
H3A0.51560.44000.89680.023*
H3B0.71950.56440.95350.023*
C40.7112 (3)0.3833 (2)0.85310 (15)0.0196 (4)
C50.8986 (3)0.4305 (3)0.87107 (18)0.0266 (5)
H50.97950.52810.90770.032*
C60.9674 (4)0.3354 (3)0.8356 (2)0.0347 (6)
H6A1.09520.36830.84820.042*
C70.8502 (4)0.1930 (3)0.7821 (2)0.0364 (6)
H70.89760.12810.75870.044*
C80.6639 (4)0.1455 (3)0.76274 (19)0.0333 (6)
H80.58330.04790.72550.040*
C90.5945 (3)0.2402 (2)0.79772 (17)0.0262 (5)
H90.46650.20710.78380.031*
C100.9974 (3)0.8461 (2)0.87082 (14)0.0162 (4)
C111.1731 (3)0.9611 (2)0.94136 (14)0.0172 (4)
C121.2677 (3)1.0766 (2)0.92264 (15)0.0202 (4)
H121.21971.07970.86420.024*
C131.4313 (3)1.1865 (2)0.98931 (16)0.0216 (4)
H131.49521.26590.97740.026*
C141.4999 (3)1.1790 (2)1.07313 (15)0.0196 (4)
C151.4091 (3)1.0649 (2)1.09321 (15)0.0200 (4)
H151.45921.06131.15110.024*
C161.2445 (3)0.9567 (2)1.02717 (15)0.0184 (4)
H161.17950.87891.04030.022*
C170.7901 (3)0.5014 (2)0.56797 (14)0.0172 (4)
C180.8251 (3)0.3815 (2)0.51698 (15)0.0173 (4)
C190.8981 (3)0.3266 (3)0.57203 (16)0.0249 (5)
H190.92710.36850.64020.030*
C200.9286 (3)0.2114 (3)0.52785 (17)0.0272 (5)
H200.97890.17400.56510.033*
C210.8842 (3)0.1515 (2)0.42783 (16)0.0209 (4)
C220.8150 (3)0.2059 (2)0.37210 (15)0.0187 (4)
H220.78780.16460.30410.022*
C230.7861 (3)0.3220 (2)0.41712 (14)0.0173 (4)
H230.73950.36100.37980.021*
C240.4283 (7)0.1015 (6)0.5053 (4)0.0873 (15)
H24A0.48840.10670.45610.131*
H24B0.30560.02210.47500.131*
H24C0.49940.08760.55430.131*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
V10.01538 (17)0.01633 (18)0.01099 (17)0.00714 (14)0.00334 (13)0.00470 (13)
Cl10.0165 (2)0.0231 (3)0.0221 (3)0.0044 (2)0.0027 (2)−0.0014 (2)
Cl20.0365 (3)0.0239 (3)0.0284 (3)0.0188 (2)0.0127 (2)0.0106 (2)
O10.0156 (7)0.0198 (7)0.0140 (7)0.0066 (6)0.0026 (5)0.0064 (6)
O20.0191 (7)0.0212 (8)0.0198 (7)0.0039 (6)0.0034 (6)0.0075 (6)
O30.0175 (7)0.0187 (7)0.0119 (7)0.0051 (6)0.0024 (5)0.0047 (6)
O40.0186 (7)0.0222 (7)0.0132 (7)0.0093 (6)0.0047 (5)0.0057 (6)
O50.0229 (7)0.0216 (7)0.0164 (7)0.0115 (6)0.0054 (6)0.0066 (6)
O60.0594 (14)0.0624 (15)0.0313 (11)0.0334 (12)0.0211 (10)0.0214 (10)
N10.0156 (8)0.0170 (8)0.0116 (7)0.0085 (7)0.0040 (6)0.0037 (6)
N20.0138 (8)0.0178 (8)0.0130 (8)0.0056 (7)0.0013 (6)0.0034 (7)
N30.0173 (8)0.0209 (9)0.0112 (8)0.0079 (7)0.0047 (6)0.0042 (7)
N40.0170 (8)0.0188 (8)0.0148 (8)0.0075 (7)0.0047 (6)0.0063 (7)
C10.0172 (9)0.0187 (10)0.0142 (9)0.0092 (8)0.0048 (8)0.0044 (8)
C20.0159 (9)0.0184 (9)0.0137 (9)0.0085 (8)0.0063 (7)0.0045 (8)
C30.0210 (10)0.0203 (10)0.0154 (9)0.0075 (8)0.0057 (8)0.0081 (8)
C40.0232 (10)0.0211 (10)0.0157 (9)0.0089 (9)0.0059 (8)0.0105 (8)
C50.0253 (11)0.0285 (12)0.0272 (12)0.0122 (10)0.0077 (9)0.0132 (10)
C60.0341 (13)0.0444 (15)0.0382 (14)0.0254 (12)0.0152 (11)0.0214 (12)
C70.0557 (17)0.0392 (14)0.0356 (14)0.0350 (14)0.0235 (13)0.0205 (12)
C80.0507 (16)0.0233 (12)0.0286 (12)0.0176 (11)0.0123 (11)0.0132 (10)
C90.0300 (12)0.0226 (11)0.0254 (11)0.0093 (10)0.0073 (9)0.0132 (9)
C100.0178 (9)0.0186 (9)0.0135 (9)0.0112 (8)0.0050 (7)0.0050 (8)
C110.0166 (9)0.0185 (10)0.0157 (9)0.0096 (8)0.0055 (8)0.0042 (8)
C120.0222 (10)0.0216 (10)0.0167 (10)0.0103 (9)0.0068 (8)0.0073 (8)
C130.0204 (10)0.0189 (10)0.0223 (11)0.0071 (8)0.0092 (8)0.0061 (8)
C140.0147 (9)0.0200 (10)0.0156 (9)0.0066 (8)0.0041 (8)−0.0004 (8)
C150.0189 (10)0.0240 (11)0.0137 (9)0.0111 (9)0.0046 (8)0.0028 (8)
C160.0180 (9)0.0184 (10)0.0162 (9)0.0076 (8)0.0057 (8)0.0048 (8)
C170.0126 (9)0.0200 (10)0.0147 (9)0.0054 (8)0.0041 (7)0.0049 (8)
C180.0140 (9)0.0180 (9)0.0158 (9)0.0055 (8)0.0045 (7)0.0044 (8)
C190.0316 (12)0.0299 (12)0.0154 (10)0.0175 (10)0.0070 (9)0.0084 (9)
C200.0339 (12)0.0318 (12)0.0249 (11)0.0210 (11)0.0098 (10)0.0151 (10)
C210.0196 (10)0.0180 (10)0.0234 (11)0.0083 (8)0.0076 (8)0.0067 (8)
C220.0150 (9)0.0197 (10)0.0166 (9)0.0057 (8)0.0043 (7)0.0052 (8)
C230.0131 (9)0.0191 (10)0.0153 (9)0.0052 (8)0.0024 (7)0.0054 (8)
C240.076 (3)0.099 (4)0.109 (4)0.038 (3)0.040 (3)0.068 (3)

Geometric parameters (Å, °)

V1—O51.5905 (15)C6—H6A0.9500
V1—N41.8797 (17)C7—C81.385 (4)
V1—O31.9697 (15)C7—H70.9500
V1—O12.0036 (15)C8—C91.389 (4)
V1—N12.0791 (17)C8—H80.9500
V1—O42.2149 (15)C9—H90.9500
Cl1—C141.744 (2)C10—C111.474 (3)
Cl2—C211.736 (2)C11—C161.395 (3)
O1—C11.310 (3)C11—C121.399 (3)
O2—C11.217 (3)C12—C131.387 (3)
O3—C101.299 (2)C12—H120.9500
O4—C171.248 (2)C13—C141.379 (3)
O6—C241.295 (6)C13—H130.9500
O6—H60.8400C14—C151.392 (3)
N1—C21.284 (3)C15—C161.383 (3)
N1—N21.376 (2)C15—H150.9500
N2—C101.318 (3)C16—H160.9500
N3—C171.342 (3)C17—C181.478 (3)
N3—N41.359 (2)C18—C191.395 (3)
N3—H30.8800C18—C231.395 (3)
N4—H40.8800C19—C201.386 (3)
C1—C21.507 (3)C19—H190.9500
C2—C31.493 (3)C20—C211.393 (3)
C3—C41.525 (3)C20—H200.9500
C3—H3A0.9900C21—C221.382 (3)
C3—H3B0.9900C22—C231.389 (3)
C4—C91.393 (3)C22—H220.9500
C4—C51.395 (3)C23—H230.9500
C5—C61.391 (4)C24—H24A0.9800
C5—H50.9500C24—H24B0.9800
C6—C71.385 (4)C24—H24C0.9800
O5—V1—N493.72 (8)C7—C8—H8119.9
O5—V1—O397.65 (7)C9—C8—H8119.9
N4—V1—O3108.53 (7)C8—C9—C4120.5 (2)
O5—V1—O198.01 (7)C8—C9—H9119.7
N4—V1—O196.05 (7)C4—C9—H9119.7
O3—V1—O1149.78 (6)O3—C10—N2123.85 (18)
O5—V1—N1112.76 (7)O3—C10—C11117.81 (18)
N4—V1—N1152.97 (7)N2—C10—C11118.34 (18)
O3—V1—N174.45 (6)C16—C11—C12119.72 (19)
O1—V1—N175.69 (6)C16—C11—C10120.61 (19)
O5—V1—O4167.39 (7)C12—C11—C10119.66 (19)
N4—V1—O473.68 (7)C13—C12—C11120.1 (2)
O3—V1—O486.92 (6)C13—C12—H12119.9
O1—V1—O483.33 (6)C11—C12—H12119.9
N1—V1—O479.76 (6)C14—C13—C12119.0 (2)
C1—O1—V1119.51 (13)C14—C13—H13120.5
C10—O3—V1116.22 (13)C12—C13—H13120.5
C17—O4—V1112.25 (13)C13—C14—C15121.97 (19)
C24—O6—H6109.5C13—C14—Cl1119.34 (17)
C2—N1—N2122.37 (17)C15—C14—Cl1118.69 (16)
C2—N1—V1118.81 (14)C16—C15—C14118.7 (2)
N2—N1—V1118.25 (13)C16—C15—H15120.7
C10—N2—N1106.72 (16)C14—C15—H15120.7
C17—N3—N4114.23 (16)C15—C16—C11120.4 (2)
C17—N3—H3122.9C15—C16—H16119.8
N4—N3—H3122.9C11—C16—H16119.8
N3—N4—V1121.55 (14)O4—C17—N3117.01 (19)
N3—N4—H4119.2O4—C17—C18123.37 (19)
V1—N4—H4119.2N3—C17—C18119.62 (18)
O2—C1—O1124.82 (19)C19—C18—C23119.9 (2)
O2—C1—C2121.66 (19)C19—C18—C17117.78 (19)
O1—C1—C2113.50 (18)C23—C18—C17122.34 (19)
N1—C2—C3126.31 (18)C20—C19—C18120.3 (2)
N1—C2—C1111.75 (18)C20—C19—H19119.8
C3—C2—C1121.66 (18)C18—C19—H19119.8
C2—C3—C4108.71 (16)C19—C20—C21118.8 (2)
C2—C3—H3A109.9C19—C20—H20120.6
C4—C3—H3A109.9C21—C20—H20120.6
C2—C3—H3B109.9C22—C21—C20121.8 (2)
C4—C3—H3B109.9C22—C21—Cl2118.73 (17)
H3A—C3—H3B108.3C20—C21—Cl2119.44 (17)
C9—C4—C5118.9 (2)C21—C22—C23118.96 (19)
C9—C4—C3120.8 (2)C21—C22—H22120.5
C5—C4—C3120.2 (2)C23—C22—H22120.5
C6—C5—C4120.4 (2)C22—C23—C18120.22 (19)
C6—C5—H5119.8C22—C23—H23119.9
C4—C5—H5119.8C18—C23—H23119.9
C7—C6—C5120.1 (2)O6—C24—H24A109.5
C7—C6—H6A119.9O6—C24—H24B109.5
C5—C6—H6A119.9H24A—C24—H24B109.5
C8—C7—C6119.9 (2)O6—C24—H24C109.5
C8—C7—H7120.0H24A—C24—H24C109.5
C6—C7—H7120.0H24B—C24—H24C109.5
C7—C8—C9120.1 (2)
O5—V1—O1—C1−118.37 (15)C2—C3—C4—C583.8 (2)
N4—V1—O1—C1147.00 (15)C9—C4—C5—C6−1.2 (3)
O3—V1—O1—C12.2 (2)C3—C4—C5—C6−178.3 (2)
N1—V1—O1—C1−6.82 (14)C4—C5—C6—C70.0 (4)
O4—V1—O1—C174.27 (14)C5—C6—C7—C80.9 (4)
O5—V1—O3—C10105.44 (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—C81.4 (3)
N1—V1—O3—C10−6.14 (14)C3—C4—C9—C8178.5 (2)
O4—V1—O3—C10−86.36 (14)V1—O3—C10—N28.3 (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—C11175.61 (16)
O1—V1—O4—C1788.58 (14)O3—C10—C11—C16−168.54 (18)
N1—V1—O4—C17165.18 (15)N2—C10—C11—C1611.6 (3)
O5—V1—N1—C2100.74 (16)O3—C10—C11—C1212.4 (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—C27.94 (15)C10—C11—C12—C13178.82 (18)
O4—V1—N1—C2−77.72 (15)C11—C12—C13—C140.9 (3)
O5—V1—N1—N2−87.67 (15)C12—C13—C14—C15−0.5 (3)
N4—V1—N1—N2104.63 (19)C12—C13—C14—Cl1179.08 (16)
O3—V1—N1—N24.23 (13)C13—C14—C15—C16−0.6 (3)
O1—V1—N1—N2179.52 (14)Cl1—C14—C15—C16179.84 (16)
O4—V1—N1—N293.86 (14)C14—C15—C16—C111.2 (3)
C2—N1—N2—C10169.75 (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—N38.5 (2)
O5—V1—N4—N3−170.15 (15)V1—O4—C17—C18−170.65 (15)
O3—V1—N4—N390.49 (15)N4—N3—C17—O4−1.4 (3)
O1—V1—N4—N3−71.68 (15)N4—N3—C17—C18177.84 (17)
N1—V1—N4—N3−1.5 (3)O4—C17—C18—C19−4.5 (3)
O4—V1—N4—N39.53 (14)N3—C17—C18—C19176.35 (19)
V1—O1—C1—O2−173.47 (16)O4—C17—C18—C23174.85 (19)
V1—O1—C1—C25.1 (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—C3166.52 (16)C17—C18—C19—C20178.0 (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—C221.6 (4)
O2—C1—C2—N1−179.70 (19)C19—C20—C21—Cl2−177.59 (19)
O1—C1—C2—N11.7 (2)C20—C21—C22—C23−1.2 (3)
O2—C1—C2—C36.0 (3)Cl2—C21—C22—C23178.00 (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—C221.8 (3)
C1—C2—C3—C480.1 (2)C17—C18—C23—C22−177.57 (18)
C2—C3—C4—C9−93.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.881.982.741 (2)143
N4—H4···O6i0.881.942.792 (3)162
O6—H6···O20.842.272.908 (3)133

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2740).

References

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