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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1014–m1015.
Published online 2008 July 9. doi:  10.1107/S1600536808020655
PMCID: PMC2961938

Tris(nitrato-κ2 O,O′)bis­(1,10-phenanthroline-κ2 N,N′)holmium(III)

Abstract

In the title compound, [Ho(NO3)3(C12H8N2)2], the ten-coordinate HoIII ion is chelated by four N atoms from two phenanthroline (phen) ligands and six O atoms from three bidentate nitrate groups. The environment around the Ho atom can be described as a distorted bicapped square anti­prism. Two phenanthroline ligands form a dihedral angle of 43.72 (13)°. Short inter­molecular distances between the centroids of the six-membered rings [3.6887 (14)–3.8374 (16) Å] indicate the existence of π–π inter­actions, which link the mol­ecules into stacks extended in the [10An external file that holds a picture, illustration, etc.
Object name is e-64-m1014-efi1.jpg] direction. The crystal packing is further stabilized by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For related literature on hydrogen bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related literature, see, for example: Frechette et al. (1992 [triangle]); Lin & Feng (2003 [triangle]); Zheng et al. (2001 [triangle]); Antsyshkina et al. (2002 [triangle]); Sadikov et al. (2006a [triangle],b [triangle]); Rybakov et al. (1991 [triangle]); Wei et al. (2002 [triangle]); Kepert et al. (1996 [triangle]); Liu et al. (2007 [triangle]); Xu et al., (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1014-scheme1.jpg

Experimental

Crystal data

  • [Ho(NO3)3(C12H8N2)2]
  • M r = 711.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1014-efi2.jpg
  • a = 11.0049 (2) Å
  • b = 17.7710 (3) Å
  • c = 12.9332 (2) Å
  • β = 100.483 (1)°
  • V = 2487.10 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.25 mm−1
  • T = 100.0 (1) K
  • 0.34 × 0.19 × 0.11 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.548, T max = 0.727
  • 39049 measured reflections
  • 7244 independent reflections
  • 6059 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.070
  • S = 1.05
  • 7244 reflections
  • 371 parameters
  • H-atom parameters constrained
  • Δρmax = 3.31 e Å−3
  • Δρmin = −1.08 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Selected interatomic distances (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020655/cv2423sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020655/cv2423Isup2.hkl

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

Acknowledgments

The authors thank Universiti Sains Malaysia and the Malaysian Government for the research grants SAGA No. 304/PKIMIA/653010/A118 and FRGS No. 203/PKIMIA/671020. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

1,10-Phenanthroline (Phen) has experienced an increasingly important role in the field of supramolecular chemistry as a ligand and sensitizer in different lanthanide complexes. The series of lanthanide nitrate complexes (La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Yb and Lu) with the Phen ligand have previously been reported (Frechette et al., 1992; Lin & Feng, 2003; Zheng et al., 2001; Antsyshkina et al., 2002; Sadikov et al., 2006a,b; Rybakov et al., 1991; Wei et al., 2002; Kepert et al., 1996; Liu et al., 2007], while crystal structure of [Ho(Phen)2(NO3)3] complex has not been reported in the literature. In these complexes, it is believed that the Phen ligand may displace the coordinated water molecules and increase the molecular rigidity to attain the high luminescence efficiency (Xu et al., 2005). Almost all of the [Ln(Phen)2(NO3)3] {Ln = La, Ce, Pr, Nd, Sm, Eu, Tb, Dy, Yb, Lu} complexes were crystallized in the monoclinic space group C2/c. In our study, the [Ho(Phen)2(NO3)3] complex was obtained from a solution mixture containing 1,10-phenanthroline, tetraethylene glycol and holmium nitrate.

In the title compound (Fig. 1), four nitrogen atoms (from two phen ligands; N1, N2, N3, and N4) and six oxygen atoms from three bidentate nitrate groups (O1, O2; O4, O5; O7, O8) are coordinated to the central HoIII ion. Bond lengths and angles have normal values (Allen et al., 1987). The dihedral angle between the two phenanthroline ligands is 43.72 (13) °.

In the crystal structure, short intermolecular distances between the centroids of six-membered rings (Table 1) prove an existence of π-π interactions, which link the molecules into stacks extended in direction [10-1]. The crystal packing is further stabilized by the weak intermolecular C—H···O hydrogen bonds (Table 2).

Experimental

The title compound was prepared by the reaction of tetraethylene glycol (0.207 g, 1.07 mmol), 1,10-phenanthroline (0.179, 1 mmol) and holmium nitrate (0.442 g, 1 mmol) in 20 ml H2O. The solution was heated for 1 h at 60°C. The solution was filtrated and was covered with an aluminium foil to enable slow evaporation at room temperature. Brown crystals were obtained after 5 months with a yield of 80%. Anal. Calc. for. [Ho(Phen)2(NO3)3]: C, 40.49; H, 2.25; N, 13.78. Found: C, 37.93; H, 2.25; N, 12.35%.

Refinement

The geometrically constrained hydrogen atoms were placed in calculated positions (C-H 0.93 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C). The highest residual peak [3.31 eÅ-3] is located 0.83 Å from Ho1 and the deepest hole [-1.08 eÅ-3] is located 2.04 Å from C15.

Figures

Fig. 1.
The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The H atoms have been omitted for clarity.

Crystal data

[Ho(NO3)3(C12H8N2)2]F000 = 1392
Mr = 711.37Dx = 1.900 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9346 reflections
a = 11.0049 (2) Åθ = 2.2–32.1º
b = 17.7710 (3) ŵ = 3.25 mm1
c = 12.9332 (2) ÅT = 100.0 (1) K
β = 100.4830 (10)ºBlock, brown
V = 2487.10 (7) Å30.34 × 0.19 × 0.11 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7244 independent reflections
Radiation source: fine-focus sealed tube6059 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 100.0(1) Kθmax = 30.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −15→15
Tmin = 0.548, Tmax = 0.727k = −25→25
39049 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.070  w = 1/[σ2(Fo2) + (0.0236P)2 + 4.9031P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.004
7244 reflectionsΔρmax = 3.31 e Å3
371 parametersΔρmin = −1.08 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)

xyzUiso*/Ueq
Ho10.488774 (10)0.175637 (6)0.238530 (8)0.01342 (3)
O10.51495 (18)0.04947 (10)0.31894 (15)0.0232 (4)
O20.48440 (18)0.05435 (10)0.14900 (15)0.0233 (4)
O30.5190 (2)−0.05374 (11)0.22803 (19)0.0394 (6)
O40.66600 (16)0.16813 (10)0.39018 (13)0.0183 (4)
O50.70134 (16)0.13574 (10)0.23748 (13)0.0188 (4)
O60.84805 (18)0.12616 (12)0.37481 (15)0.0276 (5)
O70.30817 (17)0.16390 (10)0.08994 (13)0.0195 (4)
O80.28298 (16)0.12639 (10)0.24356 (13)0.0200 (4)
O90.12801 (18)0.12176 (13)0.11134 (16)0.0312 (5)
N10.35309 (19)0.29166 (11)0.22497 (15)0.0160 (4)
N20.4282 (2)0.21458 (12)0.40627 (16)0.0173 (4)
N30.6131 (2)0.29709 (11)0.25716 (15)0.0171 (4)
N40.54335 (19)0.22274 (11)0.07176 (15)0.0156 (4)
N50.5064 (2)0.01456 (12)0.23142 (19)0.0238 (5)
N60.74234 (19)0.14297 (12)0.33588 (16)0.0177 (4)
N70.2359 (2)0.13717 (12)0.14692 (17)0.0189 (5)
C10.3141 (2)0.32922 (14)0.13647 (18)0.0186 (5)
H1A0.31940.30600.07300.022*
C20.2651 (3)0.40222 (14)0.1339 (2)0.0221 (6)
H2A0.23930.42650.07000.027*
C30.2558 (3)0.43717 (15)0.2259 (2)0.0232 (6)
H3A0.22610.48620.22540.028*
C40.2916 (2)0.39856 (14)0.3218 (2)0.0200 (5)
C50.2779 (3)0.42963 (15)0.4216 (2)0.0236 (6)
H5A0.24680.47810.42480.028*
C60.3098 (3)0.38902 (15)0.5111 (2)0.0229 (6)
H6A0.29950.41000.57490.027*
C70.3588 (2)0.31498 (14)0.50970 (18)0.0181 (5)
C80.3894 (2)0.26962 (16)0.60012 (19)0.0221 (6)
H8A0.37860.28780.66530.027*
C90.4350 (3)0.19881 (16)0.5915 (2)0.0240 (6)
H9A0.45280.16770.65020.029*
C100.4544 (2)0.17361 (15)0.49320 (19)0.0210 (5)
H10A0.48740.12580.48860.025*
C110.3779 (2)0.28392 (14)0.41332 (18)0.0159 (5)
C120.3402 (2)0.32587 (14)0.31716 (18)0.0161 (5)
C130.6460 (3)0.33423 (14)0.34675 (19)0.0208 (5)
H13A0.64070.30940.40910.025*
C140.6882 (3)0.40881 (15)0.3528 (2)0.0267 (6)
H14A0.70880.43270.41760.032*
C150.6986 (3)0.44575 (15)0.2625 (2)0.0282 (6)
H15A0.72470.49560.26480.034*
C160.6691 (3)0.40757 (15)0.1656 (2)0.0234 (6)
C170.6835 (3)0.44123 (16)0.0676 (2)0.0300 (7)
H17A0.71140.49060.06690.036*
C180.6571 (3)0.40208 (15)−0.0241 (2)0.0267 (6)
H18A0.66850.4245−0.08660.032*
C190.6119 (2)0.32673 (14)−0.02508 (18)0.0185 (5)
C200.5850 (2)0.28446 (15)−0.11786 (19)0.0206 (5)
H20A0.59760.3047−0.18140.025*
C210.5399 (2)0.21275 (15)−0.11353 (19)0.0212 (6)
H21A0.52370.1834−0.17400.025*
C220.5182 (2)0.18402 (14)−0.01784 (19)0.0185 (5)
H22A0.48480.1360−0.01670.022*
C230.5929 (2)0.29317 (14)0.06874 (18)0.0163 (5)
C240.6252 (2)0.33318 (14)0.16655 (18)0.0173 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ho10.01761 (5)0.00975 (5)0.01367 (5)0.00001 (4)0.00491 (4)−0.00004 (4)
O10.0251 (9)0.0166 (9)0.0260 (9)−0.0010 (8)−0.0006 (8)0.0047 (7)
O20.0262 (9)0.0146 (8)0.0272 (9)0.0017 (8)−0.0001 (8)−0.0017 (7)
O30.0416 (13)0.0101 (9)0.0596 (14)0.0017 (9)−0.0090 (11)−0.0001 (9)
O40.0231 (8)0.0178 (8)0.0151 (7)−0.0001 (7)0.0063 (7)−0.0008 (6)
O50.0203 (8)0.0203 (9)0.0159 (8)−0.0017 (7)0.0034 (7)−0.0014 (7)
O60.0204 (9)0.0305 (10)0.0299 (10)0.0005 (8)−0.0006 (8)0.0013 (8)
O70.0238 (9)0.0178 (9)0.0173 (8)0.0003 (7)0.0047 (7)−0.0004 (6)
O80.0219 (9)0.0208 (9)0.0169 (8)0.0005 (7)0.0029 (7)0.0022 (7)
O90.0176 (9)0.0412 (12)0.0325 (10)−0.0039 (9)−0.0015 (8)−0.0013 (9)
N10.0212 (10)0.0132 (9)0.0143 (9)0.0015 (8)0.0050 (8)0.0002 (7)
N20.0213 (10)0.0147 (9)0.0163 (9)0.0045 (8)0.0051 (8)0.0024 (7)
N30.0238 (10)0.0140 (9)0.0143 (9)−0.0035 (8)0.0058 (8)−0.0007 (7)
N40.0181 (9)0.0133 (9)0.0160 (9)−0.0008 (8)0.0047 (8)−0.0026 (7)
N50.0199 (11)0.0126 (10)0.0362 (12)0.0009 (8)−0.0025 (10)−0.0012 (9)
N60.0181 (10)0.0150 (10)0.0196 (9)−0.0033 (8)0.0024 (8)−0.0004 (8)
N70.0206 (10)0.0146 (10)0.0215 (10)0.0014 (8)0.0037 (8)−0.0003 (8)
C10.0277 (12)0.0157 (11)0.0129 (10)0.0032 (10)0.0046 (9)0.0027 (9)
C20.0313 (14)0.0172 (12)0.0186 (11)0.0058 (11)0.0061 (10)0.0057 (9)
C30.0304 (14)0.0140 (11)0.0254 (12)0.0085 (11)0.0059 (11)0.0026 (9)
C40.0258 (13)0.0128 (11)0.0217 (11)0.0033 (10)0.0054 (10)−0.0001 (9)
C50.0351 (14)0.0155 (12)0.0222 (12)0.0037 (11)0.0104 (11)−0.0034 (9)
C60.0313 (14)0.0216 (13)0.0167 (11)0.0016 (11)0.0071 (10)−0.0029 (9)
C70.0203 (11)0.0200 (12)0.0146 (10)0.0000 (10)0.0046 (9)−0.0013 (9)
C80.0257 (13)0.0308 (14)0.0111 (10)0.0019 (11)0.0065 (9)0.0003 (9)
C90.0263 (13)0.0305 (14)0.0162 (11)0.0079 (11)0.0062 (10)0.0071 (10)
C100.0253 (12)0.0213 (12)0.0175 (10)0.0076 (11)0.0067 (9)0.0059 (10)
C110.0166 (11)0.0164 (11)0.0156 (10)0.0014 (9)0.0054 (9)−0.0001 (8)
C120.0212 (11)0.0142 (10)0.0136 (9)0.0005 (10)0.0051 (8)0.0002 (8)
C130.0299 (13)0.0179 (12)0.0154 (10)−0.0038 (10)0.0066 (10)−0.0028 (9)
C140.0443 (16)0.0189 (12)0.0177 (11)−0.0097 (12)0.0076 (11)−0.0057 (10)
C150.0467 (17)0.0165 (12)0.0228 (12)−0.0122 (12)0.0105 (12)−0.0060 (10)
C160.0356 (14)0.0149 (12)0.0216 (11)−0.0057 (11)0.0107 (11)−0.0016 (9)
C170.0513 (18)0.0183 (12)0.0232 (12)−0.0137 (13)0.0138 (12)−0.0031 (10)
C180.0425 (16)0.0207 (13)0.0195 (11)−0.0093 (12)0.0126 (11)0.0004 (10)
C190.0228 (12)0.0188 (11)0.0149 (10)−0.0023 (10)0.0063 (9)−0.0008 (9)
C200.0231 (12)0.0236 (13)0.0163 (10)−0.0006 (11)0.0070 (9)0.0007 (9)
C210.0259 (13)0.0252 (13)0.0127 (10)−0.0008 (11)0.0040 (9)−0.0054 (9)
C220.0236 (12)0.0152 (11)0.0176 (10)−0.0030 (10)0.0058 (9)−0.0043 (9)
C230.0189 (11)0.0149 (11)0.0159 (10)−0.0012 (9)0.0055 (9)−0.0015 (8)
C240.0217 (11)0.0156 (11)0.0148 (10)−0.0028 (10)0.0039 (9)−0.0005 (8)

Geometric parameters (Å, °)

Ho1—O82.4398 (18)C4—C121.404 (3)
Ho1—O22.4431 (18)C4—C51.436 (4)
Ho1—O52.4468 (18)C5—C61.356 (4)
Ho1—O12.4662 (18)C5—H5A0.9300
Ho1—N22.481 (2)C6—C71.423 (4)
Ho1—N42.487 (2)C6—H6A0.9300
Ho1—O42.5053 (17)C7—C81.410 (3)
Ho1—O72.5094 (17)C7—C111.413 (3)
Ho1—N12.533 (2)C8—C91.367 (4)
Ho1—N32.544 (2)C8—H8A0.9300
Ho1—N52.872 (2)C9—C101.401 (4)
Ho1—N72.901 (2)C9—H9A0.9300
O1—N51.279 (3)C10—H10A0.9300
O2—N51.265 (3)C11—C121.445 (3)
O3—N51.223 (3)C13—C141.402 (4)
O4—N61.270 (3)C13—H13A0.9300
O5—N61.277 (3)C14—C151.362 (4)
O6—N61.218 (3)C14—H14A0.9300
O7—N71.271 (3)C15—C161.411 (4)
O8—N71.277 (3)C15—H15A0.9300
O9—N71.224 (3)C16—C241.409 (3)
N1—C11.327 (3)C16—C171.435 (4)
N1—C121.369 (3)C17—C181.361 (4)
N2—C101.326 (3)C17—H17A0.9300
N2—C111.361 (3)C18—C191.428 (4)
N3—C131.325 (3)C18—H18A0.9300
N3—C241.363 (3)C19—C201.401 (3)
N4—C221.333 (3)C19—C231.401 (3)
N4—C231.369 (3)C20—C211.373 (4)
C1—C21.403 (3)C20—H20A0.9300
C1—H1A0.9300C21—C221.399 (3)
C2—C31.362 (4)C21—H21A0.9300
C2—H2A0.9300C22—H22A0.9300
C3—C41.410 (3)C23—C241.438 (3)
C3—H3A0.9300
Cg1···Cg33.8375 (16)Cg2···Cg6i3.7641 (15)
Cg2···Cg4i3.7202 (14)Cg4···Cg5ii3.6887 (14)
O8—Ho1—O275.99 (6)O3—N5—Ho1177.36 (19)
O8—Ho1—O5142.12 (6)O2—N5—Ho157.74 (12)
O2—Ho1—O571.22 (6)O1—N5—Ho158.85 (12)
O8—Ho1—O172.57 (6)O6—N6—O4122.4 (2)
O2—Ho1—O152.30 (6)O6—N6—O5121.7 (2)
O5—Ho1—O172.57 (6)O4—N6—O5115.92 (19)
O8—Ho1—N271.23 (6)O6—N6—Ho1177.16 (17)
O2—Ho1—N2132.47 (7)O4—N6—Ho159.28 (11)
O5—Ho1—N2119.67 (6)O5—N6—Ho156.67 (11)
O1—Ho1—N285.08 (7)O9—N7—O7122.2 (2)
O8—Ho1—N4121.04 (6)O9—N7—O8121.8 (2)
O2—Ho1—N482.70 (6)O7—N7—O8116.0 (2)
O5—Ho1—N473.19 (6)O9—N7—Ho1177.83 (18)
O1—Ho1—N4130.06 (7)O7—N7—Ho159.57 (11)
N2—Ho1—N4144.11 (7)O8—N7—Ho156.46 (12)
O8—Ho1—O4123.66 (6)N1—C1—C2123.2 (2)
O2—Ho1—O4105.63 (6)N1—C1—H1A118.4
O5—Ho1—O451.68 (6)C2—C1—H1A118.4
O1—Ho1—O466.85 (6)C3—C2—C1119.4 (2)
N2—Ho1—O467.99 (6)C3—C2—H2A120.3
N4—Ho1—O4114.86 (6)C1—C2—H2A120.3
O8—Ho1—O751.75 (6)C2—C3—C4119.6 (2)
O2—Ho1—O767.62 (6)C2—C3—H3A120.2
O5—Ho1—O7126.62 (6)C4—C3—H3A120.2
O1—Ho1—O7105.24 (6)C12—C4—C3117.2 (2)
N2—Ho1—O7113.04 (6)C12—C4—C5119.7 (2)
N4—Ho1—O769.29 (6)C3—C4—C5123.1 (2)
O4—Ho1—O7172.06 (6)C6—C5—C4120.6 (2)
O8—Ho1—N175.84 (6)C6—C5—H5A119.7
O2—Ho1—N1136.45 (6)C4—C5—H5A119.7
O5—Ho1—N1141.96 (6)C5—C6—C7121.4 (2)
O1—Ho1—N1142.31 (7)C5—C6—H6A119.3
N2—Ho1—N165.46 (6)C7—C6—H6A119.3
N4—Ho1—N184.16 (7)C8—C7—C11117.2 (2)
O4—Ho1—N1117.56 (6)C8—C7—C6123.5 (2)
O7—Ho1—N168.89 (6)C11—C7—C6119.3 (2)
O8—Ho1—N3141.99 (7)C9—C8—C7119.7 (2)
O2—Ho1—N3139.24 (7)C9—C8—H8A120.2
O5—Ho1—N375.40 (6)C7—C8—H8A120.2
O1—Ho1—N3135.39 (6)C8—C9—C10119.2 (2)
N2—Ho1—N384.61 (7)C8—C9—H9A120.4
N4—Ho1—N365.53 (6)C10—C9—H9A120.4
O4—Ho1—N369.04 (6)N2—C10—C9123.2 (2)
O7—Ho1—N3118.72 (6)N2—C10—H10A118.4
N1—Ho1—N367.42 (7)C9—C10—H10A118.4
O8—Ho1—N573.26 (6)N2—C11—C7122.7 (2)
O2—Ho1—N525.97 (6)N2—C11—C12117.8 (2)
O5—Ho1—N568.94 (6)C7—C11—C12119.5 (2)
O1—Ho1—N526.35 (6)N1—C12—C4123.2 (2)
N2—Ho1—N5109.67 (7)N1—C12—C11117.5 (2)
N4—Ho1—N5106.22 (7)C4—C12—C11119.3 (2)
O4—Ho1—N585.66 (6)N3—C13—C14123.7 (2)
O7—Ho1—N586.64 (6)N3—C13—H13A118.2
N1—Ho1—N5148.39 (6)C14—C13—H13A118.2
N3—Ho1—N5144.14 (7)C15—C14—C13119.1 (2)
O8—Ho1—N725.87 (6)C15—C14—H14A120.4
O2—Ho1—N770.36 (6)C13—C14—H14A120.4
O5—Ho1—N7140.94 (6)C14—C15—C16119.3 (2)
O1—Ho1—N789.30 (6)C14—C15—H15A120.4
N2—Ho1—N791.85 (7)C16—C15—H15A120.4
N4—Ho1—N795.18 (6)C24—C16—C15117.8 (2)
O4—Ho1—N7149.26 (6)C24—C16—C17119.5 (2)
O7—Ho1—N725.89 (6)C15—C16—C17122.7 (2)
N1—Ho1—N769.75 (6)C18—C17—C16121.1 (3)
N3—Ho1—N7134.29 (6)C18—C17—H17A119.5
N5—Ho1—N779.49 (6)C16—C17—H17A119.5
N5—O1—Ho194.80 (14)C17—C18—C19120.4 (2)
N5—O2—Ho196.29 (14)C17—C18—H18A119.8
N6—O4—Ho194.87 (13)C19—C18—H18A119.8
N6—O5—Ho197.48 (14)C20—C19—C23118.2 (2)
N7—O7—Ho194.54 (13)C20—C19—C18122.0 (2)
N7—O8—Ho197.67 (14)C23—C19—C18119.9 (2)
C1—N1—C12117.3 (2)C21—C20—C19119.0 (2)
C1—N1—Ho1124.28 (16)C21—C20—H20A120.5
C12—N1—Ho1117.04 (15)C19—C20—H20A120.5
C10—N2—C11118.0 (2)C20—C21—C22119.8 (2)
C10—N2—Ho1122.42 (17)C20—C21—H21A120.1
C11—N2—Ho1119.24 (15)C22—C21—H21A120.1
C13—N3—C24117.6 (2)N4—C22—C21122.6 (2)
C13—N3—Ho1124.18 (17)N4—C22—H22A118.7
C24—N3—Ho1116.90 (15)C21—C22—H22A118.7
C22—N4—C23117.9 (2)N4—C23—C19122.5 (2)
C22—N4—Ho1122.37 (16)N4—C23—C24117.6 (2)
C23—N4—Ho1119.53 (15)C19—C23—C24120.0 (2)
O3—N5—O2122.0 (2)N3—C24—C16122.4 (2)
O3—N5—O1121.5 (2)N3—C24—C23118.5 (2)
O2—N5—O1116.5 (2)C16—C24—C23119.1 (2)
O8—Ho1—O1—N587.34 (14)O5—Ho1—N5—O2−90.17 (15)
O2—Ho1—O1—N51.82 (13)O1—Ho1—N5—O2176.7 (2)
O5—Ho1—O1—N5−77.59 (14)N2—Ho1—N5—O2154.63 (14)
N2—Ho1—O1—N5159.19 (15)N4—Ho1—N5—O2−25.95 (15)
N4—Ho1—O1—N5−28.91 (17)O4—Ho1—N5—O2−140.60 (15)
O4—Ho1—O1—N5−132.67 (15)O7—Ho1—N5—O241.35 (15)
O7—Ho1—O1—N546.63 (15)N1—Ho1—N5—O279.75 (19)
N1—Ho1—O1—N5121.68 (15)N3—Ho1—N5—O2−96.44 (16)
N3—Ho1—O1—N5−123.61 (14)N7—Ho1—N5—O266.44 (14)
N7—Ho1—O1—N567.27 (14)O8—Ho1—N5—O1−84.41 (14)
O8—Ho1—O2—N5−80.46 (15)O2—Ho1—N5—O1−176.7 (2)
O5—Ho1—O2—N580.28 (14)O5—Ho1—N5—O193.11 (14)
O1—Ho1—O2—N5−1.84 (13)N2—Ho1—N5—O1−22.08 (16)
N2—Ho1—O2—N5−33.15 (18)N4—Ho1—N5—O1157.34 (14)
N4—Ho1—O2—N5154.94 (15)O4—Ho1—N5—O142.69 (14)
O4—Ho1—O2—N541.09 (15)O7—Ho1—N5—O1−135.36 (15)
O7—Ho1—O2—N5−134.50 (16)N1—Ho1—N5—O1−96.96 (17)
N1—Ho1—O2—N5−131.53 (14)N3—Ho1—N5—O186.84 (18)
N3—Ho1—O2—N5116.95 (15)N7—Ho1—N5—O1−110.28 (15)
N7—Ho1—O2—N5−106.88 (15)Ho1—O4—N6—O6−177.3 (2)
O8—Ho1—O4—N6131.73 (13)Ho1—O4—N6—O52.2 (2)
O2—Ho1—O4—N648.37 (14)Ho1—O5—N6—O6177.3 (2)
O5—Ho1—O4—N6−1.31 (12)Ho1—O5—N6—O4−2.2 (2)
O1—Ho1—O4—N684.26 (14)O8—Ho1—N6—O660 (4)
N2—Ho1—O4—N6178.40 (15)O2—Ho1—N6—O6−7(4)
N4—Ho1—O4—N6−40.73 (14)O5—Ho1—N6—O6−55 (4)
O7—Ho1—O4—N679.4 (4)O1—Ho1—N6—O643 (4)
N1—Ho1—O4—N6−137.35 (13)N2—Ho1—N6—O6126 (4)
N3—Ho1—O4—N6−88.94 (14)N4—Ho1—N6—O6−89 (4)
N5—Ho1—O4—N665.15 (13)O4—Ho1—N6—O6127 (4)
N7—Ho1—O4—N6126.10 (15)O7—Ho1—N6—O6−36 (4)
O8—Ho1—O5—N6−96.43 (15)N1—Ho1—N6—O6−175 (4)
O2—Ho1—O5—N6−127.84 (14)N3—Ho1—N6—O6−151 (4)
O1—Ho1—O5—N6−72.61 (13)N5—Ho1—N6—O616 (4)
N2—Ho1—O5—N60.99 (15)N7—Ho1—N6—O623 (4)
N4—Ho1—O5—N6144.30 (14)O8—Ho1—N6—O4−67.52 (16)
O4—Ho1—O5—N61.30 (12)O2—Ho1—N6—O4−133.92 (13)
O7—Ho1—O5—N6−168.92 (12)O5—Ho1—N6—O4177.7 (2)
N1—Ho1—O5—N688.27 (15)O1—Ho1—N6—O4−84.47 (13)
N3—Ho1—O5—N675.92 (13)N2—Ho1—N6—O4−1.49 (14)
N5—Ho1—O5—N6−100.29 (14)N4—Ho1—N6—O4143.57 (13)
N7—Ho1—O5—N6−138.58 (13)O7—Ho1—N6—O4−163.38 (13)
O8—Ho1—O7—N71.41 (12)N1—Ho1—N6—O457.33 (16)
O2—Ho1—O7—N790.91 (14)N3—Ho1—N6—O481.45 (13)
O5—Ho1—O7—N7133.20 (13)N5—Ho1—N6—O4−110.82 (14)
O1—Ho1—O7—N753.82 (14)N7—Ho1—N6—O4−104.08 (17)
N2—Ho1—O7—N7−37.28 (15)O8—Ho1—N6—O5114.82 (14)
N4—Ho1—O7—N7−178.58 (15)O2—Ho1—N6—O548.43 (14)
O4—Ho1—O7—N758.5 (5)O1—Ho1—N6—O597.88 (14)
N1—Ho1—O7—N7−86.90 (14)N2—Ho1—N6—O5−179.14 (13)
N3—Ho1—O7—N7−133.98 (13)N4—Ho1—N6—O5−34.08 (14)
N5—Ho1—O7—N772.68 (14)O4—Ho1—N6—O5−177.7 (2)
O2—Ho1—O8—N7−73.77 (14)O7—Ho1—N6—O519.0 (2)
O5—Ho1—O8—N7−104.34 (14)N1—Ho1—N6—O5−120.32 (14)
O1—Ho1—O8—N7−128.16 (14)N3—Ho1—N6—O5−96.20 (14)
N2—Ho1—O8—N7141.16 (15)N5—Ho1—N6—O571.52 (14)
N4—Ho1—O8—N7−1.41 (16)N7—Ho1—N6—O578.27 (19)
O4—Ho1—O8—N7−173.41 (12)Ho1—O7—N7—O9178.5 (2)
O7—Ho1—O8—N7−1.41 (12)Ho1—O7—N7—O8−2.4 (2)
N1—Ho1—O8—N772.67 (14)Ho1—O8—N7—O9−178.4 (2)
N3—Ho1—O8—N787.73 (16)Ho1—O8—N7—O72.4 (2)
N5—Ho1—O8—N7−100.58 (14)O8—Ho1—N7—O939 (5)
O8—Ho1—N1—C1−103.3 (2)O2—Ho1—N7—O9137 (5)
O2—Ho1—N1—C1−52.2 (2)O5—Ho1—N7—O9148 (5)
O5—Ho1—N1—C173.7 (2)O1—Ho1—N7—O987 (5)
O1—Ho1—N1—C1−137.06 (19)N2—Ho1—N7—O92(5)
N2—Ho1—N1—C1−178.9 (2)N4—Ho1—N7—O9−142 (5)
N4—Ho1—N1—C120.7 (2)O4—Ho1—N7—O950 (5)
O4—Ho1—N1—C1135.79 (19)O7—Ho1—N7—O9−144 (5)
O7—Ho1—N1—C1−49.29 (19)N1—Ho1—N7—O9−61 (5)
N3—Ho1—N1—C186.6 (2)N3—Ho1—N7—O9−82 (5)
N5—Ho1—N1—C1−90.9 (2)N5—Ho1—N7—O9112 (5)
N7—Ho1—N1—C1−77.0 (2)O8—Ho1—N7—O7−177.5 (2)
O8—Ho1—N1—C1290.21 (17)O2—Ho1—N7—O7−79.01 (13)
O2—Ho1—N1—C12141.32 (16)O5—Ho1—N7—O7−68.22 (16)
O5—Ho1—N1—C12−92.77 (19)O1—Ho1—N7—O7−128.85 (13)
O1—Ho1—N1—C1256.5 (2)N2—Ho1—N7—O7146.10 (13)
N2—Ho1—N1—C1214.67 (16)N4—Ho1—N7—O71.33 (14)
N4—Ho1—N1—C12−145.71 (18)O4—Ho1—N7—O7−166.69 (12)
O4—Ho1—N1—C12−30.66 (19)N1—Ho1—N7—O783.15 (13)
O7—Ho1—N1—C12144.26 (19)N3—Ho1—N7—O761.82 (16)
N3—Ho1—N1—C12−79.81 (17)N5—Ho1—N7—O7−104.24 (14)
N5—Ho1—N1—C12102.60 (19)O2—Ho1—N7—O898.44 (14)
N7—Ho1—N1—C12116.57 (18)O5—Ho1—N7—O8109.23 (15)
O8—Ho1—N2—C1091.0 (2)O1—Ho1—N7—O848.61 (14)
O2—Ho1—N2—C1042.1 (2)N2—Ho1—N7—O8−36.45 (14)
O5—Ho1—N2—C10−49.0 (2)N4—Ho1—N7—O8178.79 (14)
O1—Ho1—N2—C1017.7 (2)O4—Ho1—N7—O810.8 (2)
N4—Ho1—N2—C10−151.70 (18)O7—Ho1—N7—O8177.5 (2)
O4—Ho1—N2—C10−49.29 (19)N1—Ho1—N7—O8−99.39 (14)
O7—Ho1—N2—C10122.2 (2)N3—Ho1—N7—O8−120.72 (14)
N1—Ho1—N2—C10173.6 (2)N5—Ho1—N7—O873.22 (14)
N3—Ho1—N2—C10−118.8 (2)C12—N1—C1—C22.3 (4)
N5—Ho1—N2—C1027.3 (2)Ho1—N1—C1—C2−164.1 (2)
N7—Ho1—N2—C10106.8 (2)N1—C1—C2—C3−0.3 (4)
O8—Ho1—N2—C11−96.21 (18)C1—C2—C3—C4−2.1 (4)
O2—Ho1—N2—C11−145.08 (16)C2—C3—C4—C122.4 (4)
O5—Ho1—N2—C11123.82 (17)C2—C3—C4—C5−176.2 (3)
O1—Ho1—N2—C11−169.45 (18)C12—C4—C5—C6−0.9 (4)
N4—Ho1—N2—C1121.1 (2)C3—C4—C5—C6177.7 (3)
O4—Ho1—N2—C11123.55 (19)C4—C5—C6—C70.6 (4)
O7—Ho1—N2—C11−64.97 (19)C5—C6—C7—C8−177.8 (3)
N1—Ho1—N2—C11−13.61 (17)C5—C6—C7—C111.8 (4)
N3—Ho1—N2—C1154.00 (18)C11—C7—C8—C9−0.2 (4)
N5—Ho1—N2—C11−159.81 (17)C6—C7—C8—C9179.4 (3)
N7—Ho1—N2—C11−80.32 (18)C7—C8—C9—C102.2 (4)
O8—Ho1—N3—C1369.2 (2)C11—N2—C10—C9−1.2 (4)
O2—Ho1—N3—C13−138.88 (19)Ho1—N2—C10—C9171.8 (2)
O5—Ho1—N3—C13−103.1 (2)C8—C9—C10—N2−1.6 (4)
O1—Ho1—N3—C13−57.9 (2)C10—N2—C11—C73.3 (4)
N2—Ho1—N3—C1319.4 (2)Ho1—N2—C11—C7−169.83 (18)
N4—Ho1—N3—C13179.0 (2)C10—N2—C11—C12−175.1 (2)
O4—Ho1—N3—C13−49.0 (2)Ho1—N2—C11—C1211.7 (3)
O7—Ho1—N3—C13132.8 (2)C8—C7—C11—N2−2.7 (4)
N1—Ho1—N3—C1385.1 (2)C6—C7—C11—N2177.7 (2)
N5—Ho1—N3—C13−97.1 (2)C8—C7—C11—C12175.7 (2)
N7—Ho1—N3—C13106.8 (2)C6—C7—C11—C12−3.9 (4)
O8—Ho1—N3—C24−97.43 (19)C1—N1—C12—C4−1.9 (4)
O2—Ho1—N3—C2454.5 (2)Ho1—N1—C12—C4165.5 (2)
O5—Ho1—N3—C2490.20 (18)C1—N1—C12—C11177.5 (2)
O1—Ho1—N3—C24135.39 (17)Ho1—N1—C12—C11−15.1 (3)
N2—Ho1—N3—C24−147.22 (18)C3—C4—C12—N1−0.4 (4)
N4—Ho1—N3—C2412.32 (17)C5—C4—C12—N1178.3 (2)
O4—Ho1—N3—C24144.31 (19)C3—C4—C12—C11−179.8 (2)
O7—Ho1—N3—C24−33.9 (2)C5—C4—C12—C11−1.1 (4)
N1—Ho1—N3—C24−81.59 (18)N2—C11—C12—N12.6 (3)
N5—Ho1—N3—C2496.2 (2)C7—C11—C12—N1−175.9 (2)
N7—Ho1—N3—C24−59.9 (2)N2—C11—C12—C4−178.0 (2)
O8—Ho1—N4—C22−47.9 (2)C7—C11—C12—C43.5 (4)
O2—Ho1—N4—C2220.90 (19)C24—N3—C13—C142.2 (4)
O5—Ho1—N4—C2293.42 (19)Ho1—N3—C13—C14−164.4 (2)
O1—Ho1—N4—C2244.9 (2)N3—C13—C14—C15−1.1 (5)
N2—Ho1—N4—C22−148.90 (18)C13—C14—C15—C16−1.4 (5)
O4—Ho1—N4—C22124.79 (19)C14—C15—C16—C242.5 (4)
O7—Ho1—N4—C22−47.88 (19)C14—C15—C16—C17−176.8 (3)
N1—Ho1—N4—C22−117.5 (2)C24—C16—C17—C18−0.9 (5)
N3—Ho1—N4—C22174.7 (2)C15—C16—C17—C18178.4 (3)
N5—Ho1—N4—C2232.0 (2)C16—C17—C18—C191.2 (5)
N7—Ho1—N4—C22−48.50 (19)C17—C18—C19—C20−179.3 (3)
O8—Ho1—N4—C23127.24 (17)C17—C18—C19—C231.0 (4)
O2—Ho1—N4—C23−163.98 (18)C23—C19—C20—C210.9 (4)
O5—Ho1—N4—C23−91.46 (18)C18—C19—C20—C21−178.9 (3)
O1—Ho1—N4—C23−139.93 (16)C19—C20—C21—C221.8 (4)
N2—Ho1—N4—C2326.2 (2)C23—N4—C22—C21−0.3 (4)
O4—Ho1—N4—C23−60.09 (19)Ho1—N4—C22—C21174.89 (19)
O7—Ho1—N4—C23127.24 (18)C20—C21—C22—N4−2.2 (4)
N1—Ho1—N4—C2357.63 (18)C22—N4—C23—C193.2 (4)
N3—Ho1—N4—C23−10.19 (17)Ho1—N4—C23—C19−172.13 (19)
N5—Ho1—N4—C23−152.84 (17)C22—N4—C23—C24−177.2 (2)
N7—Ho1—N4—C23126.62 (17)Ho1—N4—C23—C247.5 (3)
Ho1—O2—N5—O3−176.9 (2)C20—C19—C23—N4−3.5 (4)
Ho1—O2—N5—O13.1 (2)C18—C19—C23—N4176.3 (2)
Ho1—O1—N5—O3176.9 (2)C20—C19—C23—C24176.9 (2)
Ho1—O1—N5—O2−3.1 (2)C18—C19—C23—C24−3.4 (4)
O8—Ho1—N5—O3178 (100)C13—N3—C24—C16−0.8 (4)
O2—Ho1—N5—O385 (4)Ho1—N3—C24—C16166.8 (2)
O5—Ho1—N5—O3−5(4)C13—N3—C24—C23178.5 (2)
O1—Ho1—N5—O3−98 (4)Ho1—N3—C24—C23−13.9 (3)
N2—Ho1—N5—O3−120 (4)C15—C16—C24—N3−1.5 (4)
N4—Ho1—N5—O359 (4)C17—C16—C24—N3177.8 (3)
O4—Ho1—N5—O3−55 (4)C15—C16—C24—C23179.2 (3)
O7—Ho1—N5—O3127 (4)C17—C16—C24—C23−1.5 (4)
N1—Ho1—N5—O3165 (4)N4—C23—C24—N34.6 (4)
N3—Ho1—N5—O3−11 (4)C19—C23—C24—N3−175.7 (2)
N7—Ho1—N5—O3152 (4)N4—C23—C24—C16−176.1 (2)
O8—Ho1—N5—O292.30 (15)C19—C23—C24—C163.6 (4)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···O70.932.542.997 (3)111
C3—H3A···O8iii0.932.533.422 (3)161
C9—H9A···O3iv0.932.553.453 (3)164
C13—H13A···O40.932.543.005 (3)111
C21—H21A···O3v0.932.433.201 (3)140
C22—H22A···O20.932.593.224 (3)126

Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1, −y, −z+1; (v) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2423).

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