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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1074.
Published online 2010 August 11. doi:  10.1107/S1600536810031065
PMCID: PMC3007957

{2-[(2-Carbamothiol­ylhydrazin-1-yl­idene-κ2 N 1,S)meth­yl]-6-hy­droxy­phenolato-κO 1}(triphenyl­phosphine-κP)nickel(II) chloride

Abstract

The deprotonated Schiff base ligand in the title compound, [Ni(C8H8N3O2S)(C18H15P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated Ni atom, which exists in a distorted square-planar geometry. The hy­droxy group forms an intra­molecular O—H(...)O hydrogen bond. The two amino groups of the cation are hydrogen-bond donors to the chloride anion; the hydrogen bonds generate a chain structure running along the b axis.

Related literature

For the crystal structure of 2,3-dihy­droxy­benzaldehyde thio­semicarbazone hemihydrate, see: Swesi et al. (2006 [triangle]). For similar crystal structures containing a nickel(II) atom, see: García-Reynaldos et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1074-scheme1.jpg

Experimental

Crystal data

  • [Ni(C8H8N3O2S)(C18H15P)]Cl
  • M r = 566.66
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1074-efi1.jpg
  • a = 7.7902 (4) Å
  • b = 14.6791 (7) Å
  • c = 21.7410 (11) Å
  • V = 2486.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.07 mm−1
  • T = 100 K
  • 0.35 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.707, T max = 0.815
  • 24072 measured reflections
  • 5703 independent reflections
  • 5490 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.054
  • S = 1.02
  • 5703 reflections
  • 332 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2468 Friedel pairs
  • Flack parameter: −0.011 (7)

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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031065/bt5315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031065/bt5315Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (PS354/2009) and MOHE (FRGS-FP001/2009) for supporting this study. HBS also thanks the Libyan People’s Bureau in Malaysia for a scholarship.

supplementary crystallographic information

Comment

Substituted 2-hydroxybenzaldehyde thiosemicarbazones are generally doubly-deprotonated in their nickel complexes, the dianion chelating to the metal atom through its nitrogen, oxygen and sulfur atoms. However, with the triphenylphosphine adducts of nickel 2-hydroxybenzaldehyde thiosemicarbonates, the Schiff base is only mono-deprotonated; the positive charge of the cation is balanced by a chloride counterion (García-Reynaldos et al., 2007). The reaction of the 3-hydroxy substituted Schiff base with nickel chloride affords the analogous salt, 3-hydroxy-2-oxidobenzaldehydethiosemicarbazone)(triphenylphosphine)nickel(II) chloride (Scheme I). The coordination environment of nickel is a square plane made up of nitrogen, oxygen, phosphorus and sulfur atoms (Fig. 1). Adjacent ions are linked by N–H···Cl hydrogen bonds to generate a chain structure (Fig. 2).

Experimental

2,3-Dihydroxybenzaldehyde thiosemicarbazone hemihydrate (Swesi et al., 2006) (0.22 g, 1 mmol), triphenylphosphine (0.26, 1 mmol) and nickel chloride (0.13 g, 1 mmol) were heated in a methanol/ethanol (50 ml) for an hour. The brown solution was then set aside for the growth of crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.86±0.01 and O–H 0.84±0.01 Å; their displacement paramters were freely refined.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Hydrogen-bonded chain motif.

Crystal data

[Ni(C8H8N3O2S)(C18H15P)]ClF(000) = 1168
Mr = 566.66Dx = 1.514 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9879 reflections
a = 7.7902 (4) Åθ = 2.8–28.3°
b = 14.6791 (7) ŵ = 1.07 mm1
c = 21.7410 (11) ÅT = 100 K
V = 2486.2 (2) Å3Block, brown
Z = 40.35 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer5703 independent reflections
Radiation source: fine-focus sealed tube5490 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.707, Tmax = 0.815k = −19→19
24072 measured reflectionsl = −28→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054w = 1/[σ2(Fo2) + (0.032P)2 + 0.4343P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5703 reflectionsΔρmax = 0.29 e Å3
332 parametersΔρmin = −0.21 e Å3
4 restraintsAbsolute structure: Flack (1983), 2468 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.011 (7)

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

xyzUiso*/Ueq
Ni11.20955 (2)0.505537 (13)0.401439 (8)0.01255 (5)
Cl11.73655 (6)0.39315 (3)0.57199 (2)0.02565 (10)
S11.17398 (5)0.36636 (3)0.42809 (2)0.01724 (9)
P11.03089 (5)0.49177 (3)0.323635 (17)0.01239 (8)
O11.24123 (15)0.62350 (7)0.37422 (5)0.0187 (2)
O21.19946 (19)0.78945 (8)0.33035 (6)0.0287 (3)
N11.37566 (17)0.51529 (9)0.46493 (6)0.0149 (3)
N21.42733 (19)0.43510 (10)0.49349 (7)0.0185 (3)
N31.3866 (2)0.28145 (11)0.50486 (8)0.0241 (3)
C11.31436 (19)0.68926 (10)0.40627 (7)0.0142 (3)
C21.2891 (2)0.77878 (11)0.38354 (8)0.0176 (3)
C31.3508 (2)0.85370 (11)0.41499 (8)0.0190 (3)
H3A1.32820.91340.40020.023*
C41.4466 (3)0.84135 (12)0.46872 (8)0.0240 (4)
H4A1.48880.89280.49040.029*
C51.4800 (2)0.75525 (13)0.49031 (8)0.0214 (4)
H51.54830.74760.52610.026*
C61.4135 (2)0.67776 (11)0.45966 (7)0.0155 (3)
C71.4512 (2)0.58908 (11)0.48329 (8)0.0170 (3)
H71.53660.58400.51430.020*
C81.3423 (2)0.35953 (11)0.47936 (8)0.0178 (3)
C90.8816 (2)0.39672 (11)0.32651 (8)0.0148 (3)
C100.9418 (2)0.30780 (11)0.31890 (8)0.0185 (3)
H101.05770.29790.30710.022*
C110.8346 (2)0.23421 (12)0.32831 (8)0.0217 (4)
H110.87710.17400.32340.026*
C120.6650 (2)0.24820 (12)0.34488 (8)0.0233 (4)
H120.59190.19770.35250.028*
C130.6022 (2)0.33652 (13)0.35029 (9)0.0243 (4)
H130.48460.34600.35990.029*
C140.7092 (2)0.41065 (11)0.34182 (8)0.0201 (3)
H140.66580.47080.34640.024*
C151.1516 (2)0.47966 (10)0.25280 (7)0.0137 (3)
C161.0725 (2)0.44338 (11)0.20070 (8)0.0186 (3)
H160.96120.41720.20370.022*
C171.1566 (3)0.44565 (12)0.14459 (8)0.0243 (4)
H171.10170.42190.10900.029*
C181.3205 (2)0.48240 (12)0.13991 (8)0.0235 (4)
H181.37630.48510.10110.028*
C191.4021 (2)0.51502 (12)0.19194 (8)0.0216 (3)
H191.51580.53800.18910.026*
C201.3182 (2)0.51420 (11)0.24836 (7)0.0179 (3)
H201.37420.53720.28390.021*
C210.8940 (2)0.59074 (10)0.31157 (8)0.0137 (3)
C220.8430 (2)0.64323 (11)0.36199 (8)0.0174 (3)
H220.88510.62910.40190.021*
C230.7311 (2)0.71597 (12)0.35396 (8)0.0205 (4)
H230.69770.75170.38840.025*
C240.6678 (2)0.73673 (11)0.29596 (8)0.0212 (4)
H240.59070.78620.29070.025*
C250.7181 (2)0.68466 (11)0.24565 (8)0.0188 (3)
H250.67480.69860.20590.023*
C260.8313 (2)0.61229 (11)0.25321 (8)0.0159 (3)
H260.86610.57740.21860.019*
H11.167 (4)0.7369 (10)0.3206 (13)0.066 (9)*
H21.5176 (19)0.4328 (14)0.5163 (8)0.024 (5)*
H31.345 (3)0.2305 (10)0.4935 (10)0.034 (6)*
H41.470 (2)0.2785 (16)0.5305 (9)0.041 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.01379 (9)0.01142 (9)0.01246 (9)0.00043 (8)−0.00276 (7)0.00082 (8)
Cl10.0260 (2)0.0220 (2)0.0290 (2)0.00243 (16)−0.01141 (18)−0.00098 (17)
S10.01566 (18)0.01508 (18)0.0210 (2)−0.00126 (15)−0.00263 (16)0.00560 (15)
P10.01259 (17)0.01158 (18)0.01300 (18)−0.00005 (16)−0.00142 (13)−0.00061 (15)
O10.0255 (6)0.0114 (5)0.0190 (6)−0.0023 (5)−0.0093 (5)0.0008 (4)
O20.0330 (7)0.0164 (6)0.0368 (7)−0.0018 (6)−0.0196 (6)0.0063 (5)
N10.0150 (6)0.0171 (7)0.0126 (6)0.0033 (5)−0.0011 (5)0.0028 (5)
N20.0188 (7)0.0198 (7)0.0168 (7)0.0026 (6)−0.0063 (6)0.0040 (6)
N30.0264 (9)0.0198 (8)0.0261 (8)0.0011 (6)−0.0061 (7)0.0075 (7)
C10.0125 (7)0.0153 (7)0.0148 (7)−0.0003 (6)0.0006 (6)−0.0014 (6)
C20.0137 (7)0.0168 (7)0.0223 (8)−0.0001 (6)−0.0007 (7)−0.0003 (6)
C30.0189 (8)0.0138 (7)0.0242 (9)−0.0015 (6)0.0055 (7)−0.0019 (6)
C40.0313 (10)0.0225 (9)0.0183 (9)−0.0107 (8)0.0045 (7)−0.0054 (7)
C50.0259 (9)0.0244 (8)0.0140 (8)−0.0078 (7)−0.0005 (7)−0.0015 (7)
C60.0142 (7)0.0183 (8)0.0139 (8)−0.0018 (6)0.0002 (6)−0.0011 (6)
C70.0164 (8)0.0239 (8)0.0108 (7)−0.0009 (6)−0.0014 (6)0.0004 (6)
C80.0182 (8)0.0186 (8)0.0166 (8)0.0013 (6)0.0009 (6)0.0041 (6)
C90.0147 (7)0.0150 (7)0.0146 (8)−0.0040 (6)−0.0027 (6)−0.0019 (6)
C100.0165 (8)0.0180 (8)0.0209 (9)0.0008 (7)−0.0012 (7)−0.0018 (6)
C110.0238 (9)0.0143 (8)0.0268 (9)−0.0003 (7)−0.0037 (8)−0.0026 (7)
C120.0225 (9)0.0226 (9)0.0249 (9)−0.0088 (7)−0.0005 (7)0.0014 (7)
C130.0149 (8)0.0270 (9)0.0312 (10)−0.0025 (7)0.0042 (7)−0.0028 (8)
C140.0184 (8)0.0180 (8)0.0239 (9)0.0020 (7)0.0002 (7)−0.0032 (6)
C150.0156 (7)0.0109 (7)0.0147 (7)0.0024 (5)−0.0006 (6)−0.0004 (5)
C160.0182 (8)0.0184 (8)0.0191 (8)0.0007 (6)−0.0012 (7)−0.0032 (6)
C170.0301 (10)0.0252 (9)0.0175 (8)0.0055 (8)−0.0033 (7)−0.0079 (7)
C180.0286 (9)0.0234 (9)0.0187 (8)0.0102 (7)0.0080 (7)−0.0007 (6)
C190.0176 (8)0.0186 (8)0.0286 (9)0.0015 (7)0.0051 (7)0.0007 (7)
C200.0180 (8)0.0157 (7)0.0200 (7)0.0011 (6)−0.0008 (6)−0.0024 (6)
C210.0117 (7)0.0115 (7)0.0178 (8)−0.0005 (6)−0.0003 (6)0.0005 (6)
C220.0187 (8)0.0165 (8)0.0170 (8)−0.0006 (6)0.0004 (6)−0.0002 (6)
C230.0200 (9)0.0176 (7)0.0237 (9)0.0017 (7)0.0073 (7)−0.0015 (7)
C240.0147 (8)0.0142 (7)0.0346 (10)0.0025 (6)0.0032 (7)0.0041 (7)
C250.0157 (8)0.0179 (7)0.0228 (8)−0.0020 (7)−0.0031 (7)0.0041 (6)
C260.0156 (7)0.0154 (7)0.0169 (7)−0.0007 (6)−0.0019 (6)−0.0001 (6)

Geometric parameters (Å, °)

Ni1—O11.847 (1)C10—C111.381 (2)
Ni1—N11.897 (1)C10—H100.9500
Ni1—P12.1998 (4)C11—C121.384 (3)
Ni1—S12.1416 (4)C11—H110.9500
S1—C81.7240 (17)C12—C131.391 (3)
P1—C151.8134 (16)C12—H120.9500
P1—C91.8176 (17)C13—C141.383 (2)
P1—C211.8211 (16)C13—H130.9500
O1—C11.3198 (18)C14—H140.9500
O2—C21.360 (2)C15—C161.395 (2)
O2—H10.839 (10)C15—C201.396 (2)
N1—C71.296 (2)C16—C171.385 (2)
N1—N21.3904 (19)C16—H160.9500
N2—C81.328 (2)C17—C181.390 (3)
N2—H20.861 (9)C17—H170.9500
N3—C81.319 (2)C18—C191.383 (3)
N3—H30.850 (10)C18—H180.9500
N3—H40.857 (10)C19—C201.390 (2)
C1—C61.405 (2)C19—H190.9500
C1—C21.418 (2)C20—H200.9500
C2—C31.381 (2)C21—C261.396 (2)
C3—C41.398 (2)C21—C221.397 (2)
C3—H3A0.9500C22—C231.390 (2)
C4—C51.373 (3)C22—H220.9500
C4—H4A0.9500C23—C241.388 (3)
C5—C61.416 (2)C23—H230.9500
C5—H50.9500C24—C251.391 (2)
C6—C71.430 (2)C24—H240.9500
C7—H70.9500C25—C261.391 (2)
C9—C101.397 (2)C25—H250.9500
C9—C141.399 (2)C26—H260.9500
O1—Ni1—N194.09 (5)C11—C10—C9120.68 (16)
O1—Ni1—S1176.98 (4)C11—C10—H10119.7
N1—Ni1—S187.90 (4)C9—C10—H10119.7
O1—Ni1—P185.66 (4)C10—C11—C12119.98 (16)
N1—Ni1—P1176.19 (4)C10—C11—H11120.0
S1—Ni1—P192.207 (17)C12—C11—H11120.0
C8—S1—Ni197.58 (6)C11—C12—C13119.74 (17)
C15—P1—C9106.62 (7)C11—C12—H12120.1
C15—P1—C21105.05 (7)C13—C12—H12120.1
C9—P1—C21104.04 (7)C14—C13—C12120.68 (17)
C15—P1—Ni1109.50 (5)C14—C13—H13119.7
C9—P1—Ni1116.68 (5)C12—C13—H13119.7
C21—P1—Ni1114.07 (5)C13—C14—C9119.68 (16)
C1—O1—Ni1125.06 (10)C13—C14—H14120.2
C2—O2—H1105 (2)C9—C14—H14120.2
C7—N1—N2116.02 (13)C16—C15—C20119.55 (15)
C7—N1—Ni1126.64 (12)C16—C15—P1119.83 (12)
N2—N1—Ni1117.29 (10)C20—C15—P1120.34 (12)
C8—N2—N1117.35 (13)C17—C16—C15119.78 (16)
C8—N2—H2120.6 (14)C17—C16—H16120.1
N1—N2—H2121.7 (14)C15—C16—H16120.1
C8—N3—H3122.9 (16)C16—C17—C18120.56 (16)
C8—N3—H4121.0 (17)C16—C17—H17119.7
H3—N3—H4115 (2)C18—C17—H17119.7
O1—C1—C6125.86 (14)C19—C18—C17119.80 (16)
O1—C1—C2115.72 (14)C19—C18—H18120.1
C6—C1—C2118.42 (14)C17—C18—H18120.1
O2—C2—C3120.53 (15)C18—C19—C20120.15 (16)
O2—C2—C1118.33 (14)C18—C19—H19119.9
C3—C2—C1121.13 (15)C20—C19—H19119.9
C2—C3—C4119.75 (16)C19—C20—C15120.09 (15)
C2—C3—H3A120.1C19—C20—H20120.0
C4—C3—H3A120.1C15—C20—H20120.0
C5—C4—C3120.41 (16)C26—C21—C22119.25 (15)
C5—C4—H4A119.8C26—C21—P1121.10 (12)
C3—C4—H4A119.8C22—C21—P1119.55 (13)
C4—C5—C6120.62 (16)C23—C22—C21120.22 (15)
C4—C5—H5119.7C23—C22—H22119.9
C6—C5—H5119.7C21—C22—H22119.9
C1—C6—C5119.56 (15)C24—C23—C22120.38 (16)
C1—C6—C7121.27 (15)C24—C23—H23119.8
C5—C6—C7119.17 (15)C22—C23—H23119.8
N1—C7—C6123.88 (15)C23—C24—C25119.62 (15)
N1—C7—H7118.1C23—C24—H24120.2
C6—C7—H7118.1C25—C24—H24120.2
N3—C8—N2119.87 (16)C24—C25—C26120.36 (16)
N3—C8—S1121.41 (14)C24—C25—H25119.8
N2—C8—S1118.71 (12)C26—C25—H25119.8
C10—C9—C14119.17 (16)C25—C26—C21120.16 (16)
C10—C9—P1119.88 (13)C25—C26—H26119.9
C14—C9—P1120.69 (13)C21—C26—H26119.9
N1—Ni1—S1—C8−8.42 (7)C21—P1—C9—C10162.94 (14)
P1—Ni1—S1—C8167.76 (6)Ni1—P1—C9—C10−70.45 (15)
O1—Ni1—P1—C1576.20 (7)C15—P1—C9—C14−133.63 (14)
S1—Ni1—P1—C15−101.67 (5)C21—P1—C9—C14−22.91 (16)
O1—Ni1—P1—C9−162.64 (7)Ni1—P1—C9—C14103.70 (14)
S1—Ni1—P1—C919.49 (6)C14—C9—C10—C11−2.2 (3)
O1—Ni1—P1—C21−41.18 (7)P1—C9—C10—C11172.08 (13)
S1—Ni1—P1—C21140.95 (6)C9—C10—C11—C120.6 (3)
N1—Ni1—O1—C1−18.45 (13)C10—C11—C12—C131.8 (3)
P1—Ni1—O1—C1165.37 (13)C11—C12—C13—C14−2.7 (3)
O1—Ni1—N1—C79.88 (14)C12—C13—C14—C91.2 (3)
S1—Ni1—N1—C7−172.40 (14)C10—C9—C14—C131.2 (3)
O1—Ni1—N1—N2−167.58 (11)P1—C9—C14—C13−172.98 (14)
S1—Ni1—N1—N210.15 (11)C9—P1—C15—C1633.87 (15)
C7—N1—N2—C8174.49 (15)C21—P1—C15—C16−76.15 (14)
Ni1—N1—N2—C8−7.78 (19)Ni1—P1—C15—C16160.94 (11)
Ni1—O1—C1—C615.1 (2)C9—P1—C15—C20−152.17 (12)
Ni1—O1—C1—C2−165.23 (11)C21—P1—C15—C2097.81 (13)
O1—C1—C2—O2−2.6 (2)Ni1—P1—C15—C20−25.10 (13)
C6—C1—C2—O2177.13 (15)C20—C15—C16—C17−2.9 (2)
O1—C1—C2—C3176.23 (15)P1—C15—C16—C17171.13 (13)
C6—C1—C2—C3−4.0 (2)C15—C16—C17—C181.1 (3)
O2—C2—C3—C4−178.30 (16)C16—C17—C18—C191.6 (3)
C1—C2—C3—C42.9 (3)C17—C18—C19—C20−2.4 (3)
C2—C3—C4—C50.2 (3)C18—C19—C20—C150.6 (2)
C3—C4—C5—C6−2.0 (3)C16—C15—C20—C192.0 (2)
O1—C1—C6—C5−178.13 (16)P1—C15—C20—C19−171.93 (12)
C2—C1—C6—C52.2 (2)C15—P1—C21—C2631.84 (15)
O1—C1—C6—C72.8 (3)C9—P1—C21—C26−80.02 (14)
C2—C1—C6—C7−176.86 (16)Ni1—P1—C21—C26151.76 (12)
C4—C5—C6—C10.8 (3)C15—P1—C21—C22−151.69 (13)
C4—C5—C6—C7179.84 (17)C9—P1—C21—C2296.45 (14)
N2—N1—C7—C6−179.36 (15)Ni1—P1—C21—C22−31.77 (14)
Ni1—N1—C7—C63.2 (2)C26—C21—C22—C230.1 (2)
C1—C6—C7—N1−12.3 (3)P1—C21—C22—C23−176.48 (13)
C5—C6—C7—N1168.62 (16)C21—C22—C23—C240.5 (3)
N1—N2—C8—N3179.62 (15)C22—C23—C24—C25−0.5 (3)
N1—N2—C8—S1−0.9 (2)C23—C24—C25—C26−0.2 (3)
Ni1—S1—C8—N3−173.17 (14)C24—C25—C26—C210.7 (2)
Ni1—S1—C8—N27.37 (14)C22—C21—C26—C25−0.7 (2)
C15—P1—C9—C1052.22 (15)P1—C21—C26—C25175.82 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H1···O10.84 (1)2.11 (3)2.636 (2)120 (2)
N2—H2···Cl10.86 (1)2.17 (1)3.016 (2)167 (2)
N3—H3···Cl1i0.85 (1)2.46 (1)3.275 (2)161 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5315).

References

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