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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1366.
Published online 2010 October 9. doi:  10.1107/S1600536810039292
PMCID: PMC3009342

(6-Hydroxy-2-{[2-(N-methyl­carbamo­thiol­yl)hydrazin-1-yl­idene-κ2 N 1,S]meth­yl}­phenolato-κO 1)(triphenyl­phosphane-κP)nickel(II) chloride

Abstract

The deprotonated Schiff base ligand in the title salt, [Ni(C9H10N3O2S)(C18H15P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated nickel(II) 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

The only report of this Schiff base is that of a study of its organotin derivatives; see: Swesi et al. (2007 [triangle]). For a related nickel Schiff-base adduct of triphenyl­phosphine, see: Shawish et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1366-scheme1.jpg

Experimental

Crystal data

  • [Ni(C9H10N3O2S)(C18H15P)]Cl
  • M r = 580.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1366-efi1.jpg
  • a = 15.7781 (15) Å
  • b = 10.6306 (10) Å
  • c = 17.0020 (15) Å
  • β = 113.961 (1)°
  • V = 2606.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 100 K
  • 0.25 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.785, T max = 0.951
  • 23696 measured reflections
  • 5971 independent reflections
  • 4428 reflections with I > 2σ(I)
  • R int = 0.096

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.177
  • S = 1.05
  • 5971 reflections
  • 338 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.60 e Å−3
  • Δρmin = −1.06 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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039292/xu5041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039292/xu5041Isup2.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 thanks the Libyan People’s Bureau in Malaysia for a scholarship.

supplementary crystallographic information

Experimental

2,3-Dihydroxybenzaldehyde 4-methylthiosemicarbazone hemihydrate (Swesi et al., 2007) (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 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(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 temperature factors were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Ni(C9H10N3O2S)(C18H15P).Cl at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Hydrogen-bonded chain motif.

Crystal data

[Ni(C9H10N3O2S)(C18H15P)]ClF(000) = 1200
Mr = 580.69Dx = 1.480 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3978 reflections
a = 15.7781 (15) Åθ = 2.3–27.6°
b = 10.6306 (10) ŵ = 1.02 mm1
c = 17.0020 (15) ÅT = 100 K
β = 113.961 (1)°Triangular block, brown
V = 2606.0 (4) Å30.25 × 0.15 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5971 independent reflections
Radiation source: fine-focus sealed tube4428 reflections with I > 2σ(I)
graphiteRint = 0.096
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −20→20
Tmin = 0.785, Tmax = 0.951k = −13→13
23696 measured reflectionsl = −22→21

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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.1036P)2 + 0.1986P] where P = (Fo2 + 2Fc2)/3
5971 reflections(Δ/σ)max = 0.001
338 parametersΔρmax = 1.60 e Å3
3 restraintsΔρmin = −1.06 e Å3

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

xyzUiso*/Ueq
Ni10.41946 (3)0.54484 (4)0.60995 (3)0.01585 (16)
Cl10.66145 (6)0.16147 (8)0.61950 (6)0.0205 (2)
S10.55028 (6)0.62917 (8)0.68921 (6)0.0200 (2)
P10.34464 (6)0.68668 (9)0.65317 (6)0.0162 (2)
O10.30452 (17)0.4812 (2)0.53950 (17)0.0194 (6)
O20.12753 (18)0.4272 (3)0.45169 (19)0.0268 (6)
H2O0.159 (3)0.481 (4)0.488 (3)0.047 (16)*
N10.4861 (2)0.4179 (3)0.58096 (19)0.0170 (6)
N20.5828 (2)0.4237 (3)0.6177 (2)0.0183 (6)
H2N0.609 (3)0.353 (3)0.616 (4)0.060 (18)*
N30.7127 (2)0.5302 (3)0.7092 (2)0.0194 (7)
H3N0.739 (3)0.577 (4)0.753 (2)0.042 (15)*
C10.2882 (2)0.3775 (3)0.4925 (2)0.0185 (7)
C20.1937 (2)0.3465 (3)0.4458 (2)0.0194 (8)
C30.1667 (3)0.2402 (4)0.3963 (3)0.0226 (8)
H30.10270.22110.36650.027*
C40.2342 (3)0.1597 (3)0.3899 (3)0.0230 (8)
H40.21560.08540.35610.028*
C50.3271 (3)0.1876 (3)0.4321 (2)0.0208 (8)
H50.37230.13400.42620.025*
C60.3553 (2)0.2978 (3)0.4851 (2)0.0178 (7)
C70.4516 (3)0.3234 (3)0.5293 (2)0.0187 (7)
H70.49380.26740.52050.022*
C80.6223 (2)0.5188 (3)0.6721 (2)0.0180 (7)
C90.7785 (3)0.4427 (4)0.6972 (3)0.0231 (8)
H9A0.84130.47750.72420.035*
H9B0.76180.43060.63560.035*
H9C0.77630.36170.72380.035*
C100.3352 (3)0.6414 (3)0.7521 (2)0.0197 (8)
C110.3826 (3)0.5350 (3)0.7982 (3)0.0236 (8)
H110.42010.48650.77780.028*
C120.3746 (3)0.5011 (4)0.8736 (3)0.0325 (10)
H120.40750.43000.90520.039*
C130.3190 (3)0.5697 (4)0.9031 (3)0.0342 (10)
H130.31300.54450.95420.041*
C140.2719 (3)0.6755 (4)0.8584 (3)0.0299 (9)
H140.23450.72330.87930.036*
C150.2798 (3)0.7105 (4)0.7838 (3)0.0242 (8)
H150.24730.78250.75320.029*
C160.3967 (2)0.8436 (3)0.6713 (2)0.0187 (7)
C170.4240 (2)0.8905 (4)0.6092 (2)0.0208 (8)
H170.41460.84160.55960.025*
C180.4653 (3)1.0087 (4)0.6187 (3)0.0229 (8)
H180.48271.04100.57530.028*
C190.4808 (3)1.0785 (4)0.6917 (3)0.0253 (8)
H190.50931.15880.69880.030*
C200.4549 (3)1.0321 (4)0.7544 (3)0.0249 (9)
H200.46551.08100.80430.030*
C210.4132 (2)0.9143 (4)0.7454 (2)0.0205 (8)
H210.39630.88240.78920.025*
C220.2247 (2)0.7088 (3)0.5762 (2)0.0186 (7)
C230.1512 (3)0.6499 (4)0.5882 (3)0.0219 (8)
H230.16360.59830.63730.026*
C240.0605 (3)0.6665 (4)0.5290 (3)0.0255 (9)
H240.01100.62770.53800.031*
C250.0422 (3)0.7399 (4)0.4563 (3)0.0250 (9)
H25−0.01990.75240.41590.030*
C260.1149 (3)0.7950 (4)0.4429 (3)0.0279 (9)
H260.10230.84350.39240.033*
C270.2057 (3)0.7801 (4)0.5021 (2)0.0218 (8)
H270.25490.81850.49220.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0167 (3)0.0092 (3)0.0194 (3)−0.00037 (16)0.0050 (2)−0.00177 (17)
Cl10.0221 (4)0.0127 (4)0.0235 (5)0.0019 (3)0.0060 (4)0.0012 (3)
S10.0185 (4)0.0130 (4)0.0248 (5)−0.0006 (3)0.0051 (4)−0.0051 (4)
P10.0178 (4)0.0110 (4)0.0183 (5)−0.0007 (3)0.0058 (4)−0.0012 (4)
O10.0177 (12)0.0122 (13)0.0250 (14)−0.0008 (10)0.0054 (11)−0.0056 (10)
O20.0198 (13)0.0210 (15)0.0362 (17)−0.0019 (11)0.0080 (12)−0.0132 (13)
N10.0157 (14)0.0116 (14)0.0200 (16)−0.0006 (11)0.0034 (12)0.0024 (12)
N20.0172 (15)0.0120 (15)0.0227 (17)0.0010 (12)0.0049 (13)−0.0024 (13)
N30.0180 (15)0.0152 (16)0.0213 (17)−0.0026 (12)0.0041 (13)0.0000 (13)
C10.0243 (18)0.0105 (17)0.0180 (18)−0.0020 (14)0.0057 (15)0.0001 (14)
C20.0174 (17)0.0165 (18)0.0221 (19)−0.0011 (14)0.0058 (15)−0.0016 (15)
C30.0205 (17)0.0198 (19)0.023 (2)−0.0044 (15)0.0041 (15)−0.0044 (16)
C40.029 (2)0.0123 (18)0.024 (2)−0.0029 (15)0.0067 (16)−0.0063 (15)
C50.0253 (19)0.0107 (17)0.024 (2)0.0030 (14)0.0070 (16)−0.0024 (15)
C60.0205 (17)0.0145 (18)0.0170 (18)−0.0014 (13)0.0063 (15)−0.0001 (14)
C70.0236 (18)0.0126 (17)0.0176 (19)0.0026 (14)0.0058 (15)0.0006 (14)
C80.0203 (17)0.0131 (17)0.0186 (18)0.0006 (14)0.0057 (15)0.0047 (14)
C90.0187 (18)0.0173 (19)0.030 (2)0.0020 (14)0.0070 (16)−0.0015 (16)
C100.0255 (18)0.0146 (18)0.0196 (19)−0.0047 (14)0.0098 (16)−0.0039 (15)
C110.031 (2)0.0152 (19)0.023 (2)−0.0004 (15)0.0088 (17)−0.0022 (15)
C120.046 (3)0.019 (2)0.031 (2)−0.0069 (19)0.014 (2)0.0020 (18)
C130.052 (3)0.028 (2)0.027 (2)−0.016 (2)0.021 (2)−0.0039 (19)
C140.037 (2)0.030 (2)0.027 (2)−0.0101 (18)0.0175 (19)−0.0093 (18)
C150.0259 (19)0.019 (2)0.027 (2)−0.0037 (15)0.0105 (17)−0.0042 (16)
C160.0175 (17)0.0104 (17)0.024 (2)0.0028 (13)0.0037 (15)0.0021 (14)
C170.0222 (18)0.0151 (19)0.023 (2)−0.0037 (14)0.0070 (16)−0.0021 (15)
C180.0255 (19)0.0163 (19)0.026 (2)−0.0020 (15)0.0091 (16)0.0058 (16)
C190.0246 (19)0.0144 (18)0.033 (2)−0.0032 (15)0.0083 (17)−0.0002 (17)
C200.027 (2)0.018 (2)0.027 (2)−0.0009 (15)0.0078 (17)−0.0056 (16)
C210.0233 (18)0.0164 (18)0.022 (2)−0.0010 (14)0.0088 (15)−0.0021 (15)
C220.0183 (17)0.0152 (18)0.0187 (19)0.0013 (14)0.0039 (14)−0.0060 (14)
C230.0232 (18)0.0143 (18)0.028 (2)0.0011 (14)0.0107 (16)−0.0017 (16)
C240.0212 (19)0.022 (2)0.033 (2)−0.0039 (15)0.0106 (17)−0.0085 (17)
C250.0175 (17)0.025 (2)0.025 (2)0.0038 (15)0.0007 (15)−0.0066 (17)
C260.030 (2)0.022 (2)0.024 (2)0.0044 (16)0.0042 (17)0.0000 (17)
C270.0228 (18)0.021 (2)0.020 (2)0.0019 (15)0.0077 (15)0.0003 (15)

Geometric parameters (Å, °)

Ni1—N11.895 (3)C10—C151.406 (5)
Ni1—O11.849 (2)C11—C121.385 (6)
Ni1—P12.216 (1)C11—H110.9500
Ni1—S12.150 (1)C12—C131.382 (7)
S1—C81.738 (4)C12—H120.9500
P1—C101.813 (4)C13—C141.391 (7)
P1—C221.826 (4)C13—H130.9500
P1—C161.830 (4)C14—C151.376 (6)
O1—C11.324 (4)C14—H140.9500
O2—C21.386 (4)C15—H150.9500
O2—H2O0.84 (5)C16—C171.385 (5)
N1—C71.299 (5)C16—C211.397 (5)
N1—N21.396 (4)C17—C181.394 (5)
N2—C81.341 (5)C17—H170.9500
N2—H2N0.86 (4)C18—C191.380 (6)
N3—C81.311 (5)C18—H180.9500
N3—C91.468 (5)C19—C201.378 (6)
N3—H3N0.86 (4)C19—H190.9500
C1—C61.401 (5)C20—C211.393 (5)
C1—C21.415 (5)C20—H200.9500
C2—C31.369 (5)C21—H210.9500
C3—C41.405 (5)C22—C271.395 (5)
C3—H30.9500C22—C231.405 (5)
C4—C51.377 (5)C23—C241.386 (5)
C4—H40.9500C23—H230.9500
C5—C61.434 (5)C24—C251.389 (6)
C5—H50.9500C24—H240.9500
C6—C71.422 (5)C25—C261.387 (6)
C7—H70.9500C25—H250.9500
C9—H9A0.9800C26—C271.385 (5)
C9—H9B0.9800C26—H260.9500
C9—H9C0.9800C27—H270.9500
C10—C111.406 (5)
O1—Ni1—N194.19 (12)C11—C10—C15118.6 (4)
O1—Ni1—S1176.80 (9)C11—C10—P1120.4 (3)
N1—Ni1—S188.09 (9)C15—C10—P1121.0 (3)
O1—Ni1—P187.10 (8)C12—C11—C10119.9 (4)
N1—Ni1—P1175.83 (10)C12—C11—H11120.1
S1—Ni1—P190.78 (4)C10—C11—H11120.1
C8—S1—Ni198.04 (13)C13—C12—C11120.5 (4)
C10—P1—C22104.30 (17)C13—C12—H12119.7
C10—P1—C16106.66 (18)C11—C12—H12119.7
C22—P1—C16105.45 (17)C12—C13—C14120.3 (4)
C10—P1—Ni1112.48 (13)C12—C13—H13119.8
C22—P1—Ni1112.74 (12)C14—C13—H13119.8
C16—P1—Ni1114.42 (12)C15—C14—C13119.6 (4)
C1—O1—Ni1126.5 (2)C15—C14—H14120.2
C2—O2—H2O104 (4)C13—C14—H14120.2
C7—N1—N2114.7 (3)C14—C15—C10121.0 (4)
C7—N1—Ni1127.0 (3)C14—C15—H15119.5
N2—N1—Ni1118.3 (2)C10—C15—H15119.5
C8—N2—N1117.3 (3)C17—C16—C21119.4 (3)
C8—N2—H2N125 (4)C17—C16—P1117.2 (3)
N1—N2—H2N114 (4)C21—C16—P1123.3 (3)
C8—N3—C9124.6 (3)C16—C17—C18120.8 (4)
C8—N3—H3N121 (3)C16—C17—H17119.6
C9—N3—H3N112 (3)C18—C17—H17119.6
O1—C1—C6126.1 (3)C19—C18—C17119.4 (4)
O1—C1—C2115.8 (3)C19—C18—H18120.3
C6—C1—C2118.1 (3)C17—C18—H18120.3
C3—C2—O2120.0 (3)C20—C19—C18120.3 (4)
C3—C2—C1122.1 (3)C20—C19—H19119.9
O2—C2—C1118.0 (3)C18—C19—H19119.9
C2—C3—C4119.6 (3)C19—C20—C21120.7 (4)
C2—C3—H3120.2C19—C20—H20119.6
C4—C3—H3120.2C21—C20—H20119.6
C5—C4—C3120.5 (3)C20—C21—C16119.3 (4)
C5—C4—H4119.7C20—C21—H21120.3
C3—C4—H4119.7C16—C21—H21120.3
C4—C5—C6119.8 (3)C27—C22—C23119.1 (3)
C4—C5—H5120.1C27—C22—P1119.8 (3)
C6—C5—H5120.1C23—C22—P1121.0 (3)
C1—C6—C7121.4 (3)C24—C23—C22120.5 (4)
C1—C6—C5119.8 (3)C24—C23—H23119.8
C7—C6—C5118.8 (3)C22—C23—H23119.8
N1—C7—C6124.8 (3)C23—C24—C25119.9 (4)
N1—C7—H7117.6C23—C24—H24120.0
C6—C7—H7117.6C25—C24—H24120.0
N3—C8—N2120.7 (3)C26—C25—C24119.7 (3)
N3—C8—S1121.0 (3)C26—C25—H25120.1
N2—C8—S1118.2 (3)C24—C25—H25120.1
N3—C9—H9A109.5C27—C26—C25120.8 (4)
N3—C9—H9B109.5C27—C26—H26119.6
H9A—C9—H9B109.5C25—C26—H26119.6
N3—C9—H9C109.5C26—C27—C22119.9 (4)
H9A—C9—H9C109.5C26—C27—H27120.0
H9B—C9—H9C109.5C22—C27—H27120.0
N1—Ni1—S1—C8−1.59 (15)C22—P1—C10—C11130.3 (3)
P1—Ni1—S1—C8174.39 (13)C16—P1—C10—C11−118.5 (3)
O1—Ni1—P1—C1095.87 (15)Ni1—P1—C10—C117.8 (3)
S1—Ni1—P1—C10−86.52 (13)C22—P1—C10—C15−49.1 (3)
O1—Ni1—P1—C22−21.73 (16)C16—P1—C10—C1562.2 (3)
S1—Ni1—P1—C22155.87 (14)Ni1—P1—C10—C15−171.6 (3)
O1—Ni1—P1—C16−142.22 (16)C15—C10—C11—C12−0.5 (6)
S1—Ni1—P1—C1635.38 (14)P1—C10—C11—C12−179.8 (3)
N1—Ni1—O1—C12.5 (3)C10—C11—C12—C131.1 (6)
P1—Ni1—O1—C1−173.5 (3)C11—C12—C13—C14−1.4 (7)
O1—Ni1—N1—C7−1.3 (3)C12—C13—C14—C151.0 (6)
S1—Ni1—N1—C7−179.0 (3)C13—C14—C15—C10−0.3 (6)
O1—Ni1—N1—N2178.6 (3)C11—C10—C15—C140.1 (6)
S1—Ni1—N1—N20.8 (2)P1—C10—C15—C14179.4 (3)
C7—N1—N2—C8−179.4 (3)C10—P1—C16—C17170.3 (3)
Ni1—N1—N2—C80.7 (4)C22—P1—C16—C17−79.2 (3)
Ni1—O1—C1—C6−2.1 (5)Ni1—P1—C16—C1745.3 (3)
Ni1—O1—C1—C2178.1 (3)C10—P1—C16—C21−6.8 (4)
O1—C1—C2—C3−178.3 (4)C22—P1—C16—C21103.7 (3)
C6—C1—C2—C32.0 (6)Ni1—P1—C16—C21−131.9 (3)
O1—C1—C2—O21.3 (5)C21—C16—C17—C18−1.9 (5)
C6—C1—C2—O2−178.5 (3)P1—C16—C17—C18−179.2 (3)
O2—C2—C3—C4179.2 (4)C16—C17—C18—C191.4 (6)
C1—C2—C3—C4−1.2 (6)C17—C18—C19—C20−0.5 (6)
C2—C3—C4—C5−0.7 (6)C18—C19—C20—C210.3 (6)
C3—C4—C5—C61.8 (6)C19—C20—C21—C16−0.8 (6)
O1—C1—C6—C7−0.4 (6)C17—C16—C21—C201.6 (5)
C2—C1—C6—C7179.3 (3)P1—C16—C21—C20178.7 (3)
O1—C1—C6—C5179.4 (3)C10—P1—C22—C27160.2 (3)
C2—C1—C6—C5−0.9 (5)C16—P1—C22—C2748.1 (3)
C4—C5—C6—C1−0.9 (6)Ni1—P1—C22—C27−77.4 (3)
C4—C5—C6—C7178.8 (4)C10—P1—C22—C23−23.0 (3)
N2—N1—C7—C6179.6 (3)C16—P1—C22—C23−135.1 (3)
Ni1—N1—C7—C6−0.6 (5)Ni1—P1—C22—C2399.4 (3)
C1—C6—C7—N11.8 (6)C27—C22—C23—C24−2.6 (5)
C5—C6—C7—N1−178.0 (3)P1—C22—C23—C24−179.4 (3)
C9—N3—C8—N2−1.2 (6)C22—C23—C24—C251.2 (6)
C9—N3—C8—S1−178.9 (3)C23—C24—C25—C260.8 (6)
N1—N2—C8—N3179.9 (3)C24—C25—C26—C27−1.5 (6)
N1—N2—C8—S1−2.3 (4)C25—C26—C27—C220.1 (6)
Ni1—S1—C8—N3−179.7 (3)C23—C22—C27—C261.9 (6)
Ni1—S1—C8—N22.5 (3)P1—C22—C27—C26178.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.84 (5)2.10 (4)2.640 (4)122 (4)
N2—H2N···Cl10.86 (4)2.19 (4)3.046 (3)172 (5)
N3—H3N···Cl1i0.86 (4)2.28 (4)3.111 (3)164 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5041).

References

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