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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1318–o1319.
Published online 2008 June 21. doi:  10.1107/S1600536808018485
PMCID: PMC2961663

Dibenzo-18-crown-6–picric acid–water (1/2/3)

Abstract

In the crown ether ring of the title compound, C20H24O6·2C6H3N3O7·3H2O, the O—C(H2)—C(H2)—O torsion angles indicate a gauche conformation of the ethyl­eneoxy units, while the C—O—C—C torsion angles indicate planarity of these segments; the dihedral angle between the two benzene rings is 44.53 (13)°. In both picric acid mol­ecules, one of the nitro groups is twisted away from the attached ring. The mol­ecules are linked into chains along the b axis via inter­molecular O—H(...)O hydrogen bonds. In addition, the crystal structure is stabilized by C—H(...)O hydrogen bonds and π–π inter­actions [centroid–centroid distance between benzene rings = 3.5697 (16) Å].

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For related literature, see: Bush & Truter (1971 [triangle]); Colquhoun et al. (1986 [triangle]); Kanters et al. (1986 [triangle]); Lu et al. (1993a [triangle],b [triangle]); Robinson et al. (1987 [triangle]); Saleh et al. (1996 [triangle], 1997 [triangle]); You et al. (2002 [triangle]); Zhou et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1318-scheme1.jpg

Experimental

Crystal data

  • C20H24O6·2C6H3N3O7·3H2O
  • M r = 872.67
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1318-efi1.jpg
  • a = 16.4192 (2) Å
  • b = 7.0845 (1) Å
  • c = 31.4135 (4) Å
  • V = 3654.08 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 100.0 (1) K
  • 0.36 × 0.32 × 0.16 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.952, T max = 0.979
  • 37248 measured reflections
  • 5431 independent reflections
  • 4559 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.110
  • S = 1.06
  • 5431 reflections
  • 550 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.33 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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018485/ci2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018485/ci2617Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for providing SAGA (No. 304/PKIMIA/653010/A118) and FRGS (No.203/PKIMIA/671020) research grants.

supplementary crystallographic information

Comment

The lanthanide complexes with crown ethers have been previously reported e.g. [Ln(NO3)2(H2O)2(DB30C10)2].[Ln(NO3)5]. CH3CN {Ln = Sm - Lu} (Lu et al., 1993a), [Gd(NO3)3(H2O)3].(DB24C8) (Lu et al., 1993b) and Ln(Pic)3.(B15C5)2nH2O {Ln = Nd, Sm, Er} (Zhou et al., 1996) where DB30C10 is dibenzo-30-crown-10, DB24C8 is dibenzo-24-crown-8, B15C5 is benzo-15-crown-5 and Pic is picrate anion. The complexation of dibenzo-18-crown-6 (DB18C6) with alkali and transition metal ions have also been reported e.g. NaBr(DB18C6).2H2O (Bush & Truter, 1971), [Ga(CH3)3]2(DB18C6) (Robinson et al., 1987) and [(H3O(DB18C6)]2[HPMo12O40].DB18C6.3CH3CN.H2O (You et al., 2002) where HPMo12O40 is 12-molybdophosphate acid. Additionally, different products without lanthanide coordination with crown ether in the presence of picric acid have also been observed namely [NH4(Pic)(DB18C6)] (Kanters et al., 1986), DB18C6.2HPic and DB24C8.2HPic (Colquhoun et al., 1986), D15C5.2HPic (Saleh et al., 1996) where DD18C6 is N,N'-dibenzyl-1,14, 10,13,-tetraoxa-7,16-diazacyclooctadecane.

In our study, no complexation product was obtained from a solution mixture containing dibenzo-18-crown-6, terbium nitrate and picric acid and instead the formation of DB18C6 with three water molecules in the presence of two picric acid have taken place. The product has a red colour consistent with a charge transfer interaction between the π-electron-rich benzene rings of the DB18C6 and the lack of π-electron in the HPic molecules.

The molecular structure of the title compound is shown in Fig.1. Bond lengths and angles have normal values (Allen et al., 1987). The dihedral angle between the two benzene rings (C1-C6 and C11-C16) in dibenzo-18-crown-6 unit is 44.53 (13)°. In the crown ether, the O-C(H2)-C(H2)-O torsion angles indicate a gauche conformation of the ethyleneoxy units, while the C-O-C-C torsion angles indicate planarity of these segments. In both picric acid units, one of the nitro groups is twisted away from the attached ring [O8—N1—C22—C21 = 52.9 (4)°, O9—N1—C22—C23 49.9 (4)°, O15—N4—C28—C29 = 146.4 (3)° and O16—N4—C28—C27 = 148.9 (3)°].

In the crystal structure, O—H···O, O—H···N and C—H···O hydrogen bonds are observed (Table 1). The molecules are linked into chains along the b axis via intermolecular O—H···O hydrogen bonds (Fig. 2). In addition, π-π interactions involving the C1-C6 (centroid Cg1) and C27-C32 (centroid Cg2) benzene rings are observed, with a Cg1···Cg2(x, -1+y, z) distance of 3.5697 (16) Å.

Experimental

The title compound was prepared by the reaction of dibenzo-18-crown-6 (0.17 g, 0.46 mmol) and terbium nitrate (0.43 g, 1 mmol) in the presence of picric acid (0.93 g, 4.06 mmol) in a CH3CN-CH3OH-CHCl3-H2O (2:1:1:1 v/v) solution (20 ml). The solution was heated in a water bath with continous stirring for 5 min at 313-323 K. The solution was left to evaporate at room temperature. Red crystals were obtained after one week (yield 90%, decomposition point 381.6-412.0 K). Elemental analysis data: Calcuclated (found): C 44.00 (45.87), H 4.13 (4.32), N 9.63 (8.38)%.

Refinement

O-bound H atoms were located initially in a difference Fourier map and then constrained to ride on the parent O atom. C-bound H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.97 Å. All H atoms were refined with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C20H24O6·2C6H3N3O7·3H2OF000 = 1816
Mr = 872.67Dx = 1.586 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8814 reflections
a = 16.4192 (2) Åθ = 2.6–30.1º
b = 7.0845 (1) ŵ = 0.14 mm1
c = 31.4135 (4) ÅT = 100.0 (1) K
V = 3654.08 (8) Å3Block, red
Z = 40.36 × 0.32 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5431 independent reflections
Radiation source: fine-focus sealed tube4559 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
Detector resolution: 8.33 pixels mm-1θmax = 30.1º
T = 100.0(1) Kθmin = 2.5º
ω scansh = −17→23
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −9→9
Tmin = 0.952, Tmax = 0.979l = −43→44
37248 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0586P)2 + 0.3893P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5431 reflectionsΔρmax = 0.40 e Å3
550 parametersΔρmin = −0.33 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O10.17228 (11)0.0965 (3)0.33490 (6)0.0194 (4)
O20.02175 (11)0.0646 (3)0.31441 (6)0.0205 (4)
O3−0.03139 (11)0.0282 (3)0.22594 (6)0.0225 (4)
O40.09157 (11)0.0249 (3)0.16058 (6)0.0239 (4)
O50.23885 (11)0.0985 (3)0.18147 (6)0.0226 (4)
O60.29382 (11)0.1294 (3)0.26846 (6)0.0193 (4)
C10.11872 (16)0.1717 (4)0.36375 (8)0.0179 (5)
C20.13993 (16)0.2525 (4)0.40216 (8)0.0197 (5)
H2A0.19440.26130.40990.024*
C30.07934 (18)0.3210 (4)0.42944 (8)0.0220 (5)
H3A0.09360.37560.45530.026*
C4−0.00162 (18)0.3077 (4)0.41795 (9)0.0233 (6)
H4A−0.04180.35460.43600.028*
C5−0.02333 (17)0.2239 (4)0.37928 (8)0.0208 (5)
H5A−0.07800.21410.37180.025*
C60.03588 (16)0.1556 (4)0.35220 (8)0.0194 (5)
C7−0.06112 (16)0.0602 (4)0.30033 (9)0.0219 (5)
H7A−0.07940.18670.29340.026*
H7B−0.09580.01070.32270.026*
C8−0.06605 (16)−0.0636 (4)0.26173 (8)0.0230 (6)
H8A−0.0373−0.18080.26710.028*
H8B−0.1226−0.09380.25590.028*
C9−0.02913 (17)−0.0983 (5)0.19033 (9)0.0260 (6)
H9A−0.0838−0.14130.18380.031*
H9B0.0038−0.20770.19730.031*
C100.00626 (17)0.0008 (5)0.15248 (9)0.0264 (6)
H10A−0.0019−0.07380.12690.032*
H10B−0.01970.12250.14850.032*
C110.13815 (17)0.1008 (4)0.12882 (8)0.0208 (5)
C120.11157 (18)0.1340 (4)0.08740 (9)0.0247 (6)
H12A0.05770.11050.07990.030*
C130.16674 (19)0.2032 (4)0.05716 (9)0.0278 (6)
H13A0.14960.22470.02940.033*
C140.24573 (19)0.2392 (4)0.06832 (9)0.0277 (6)
H14A0.28190.28460.04800.033*
C150.27260 (18)0.2088 (4)0.10966 (9)0.0243 (6)
H15A0.32630.23460.11700.029*
C160.21896 (18)0.1396 (4)0.14004 (8)0.0217 (5)
C170.32251 (16)0.1243 (4)0.19333 (9)0.0234 (6)
H17A0.33510.25770.19550.028*
H17B0.35800.06860.17210.028*
C180.33476 (16)0.0296 (4)0.23549 (9)0.0230 (6)
H18A0.3142−0.09860.23410.028*
H18B0.39250.02380.24190.028*
C190.30305 (16)0.0303 (4)0.30759 (8)0.0201 (5)
H19A0.36030.02370.31500.024*
H19B0.2829−0.09770.30440.024*
C200.25708 (15)0.1275 (4)0.34246 (8)0.0200 (5)
H20A0.27260.07620.36990.024*
H20B0.26900.26160.34230.024*
O70.04207 (12)0.5129 (3)0.14168 (6)0.0255 (4)
H1O70.07680.50630.16760.038*
O8−0.08444 (13)0.6214 (3)0.09050 (7)0.0345 (5)
O9−0.05274 (14)0.4429 (4)0.03674 (7)0.0388 (6)
O100.18091 (15)0.7752 (5)−0.03288 (7)0.0483 (7)
O110.28256 (15)0.8540 (4)0.00640 (8)0.0461 (7)
O120.28468 (13)0.6902 (4)0.15276 (8)0.0399 (6)
O130.18305 (14)0.5543 (4)0.18259 (7)0.0398 (6)
N1−0.03549 (14)0.5511 (4)0.06579 (8)0.0251 (5)
N20.21475 (14)0.7882 (4)0.00136 (8)0.0273 (5)
N30.21571 (15)0.6291 (3)0.15208 (8)0.0264 (5)
C210.08740 (17)0.5840 (4)0.11077 (8)0.0219 (5)
C220.05087 (16)0.6039 (4)0.07059 (9)0.0212 (5)
C230.09073 (16)0.6653 (4)0.03478 (9)0.0215 (5)
H23A0.06460.67010.00850.026*
C240.17102 (16)0.7197 (4)0.03915 (9)0.0229 (5)
C250.21134 (16)0.7102 (4)0.07728 (9)0.0228 (6)
H25A0.26530.74860.07950.027*
C260.16965 (17)0.6419 (4)0.11252 (9)0.0223 (5)
O140.20351 (12)0.6284 (3)0.35095 (6)0.0259 (4)
H14B0.17750.58830.33210.039*
O150.32541 (13)0.5815 (4)0.40398 (8)0.0403 (6)
O160.33764 (14)0.8326 (4)0.44252 (8)0.0440 (6)
O170.09655 (17)1.0026 (4)0.52185 (7)0.0429 (6)
O18−0.02186 (15)0.9577 (3)0.49381 (8)0.0367 (5)
O19−0.04855 (12)0.6963 (3)0.35674 (7)0.0290 (5)
O200.05487 (13)0.5990 (3)0.32031 (6)0.0302 (5)
N40.29744 (15)0.7191 (4)0.42194 (8)0.0304 (6)
N50.05197 (17)0.9451 (4)0.49329 (8)0.0299 (6)
N60.02454 (15)0.6709 (3)0.35237 (8)0.0241 (5)
C270.16382 (16)0.6979 (4)0.38383 (8)0.0195 (5)
C280.20853 (16)0.7523 (4)0.42021 (9)0.0222 (5)
C290.17357 (18)0.8335 (4)0.45523 (9)0.0245 (6)
H29A0.20550.87200.47810.029*
C300.09002 (17)0.8576 (4)0.45611 (8)0.0216 (5)
C310.04172 (17)0.8047 (4)0.42235 (9)0.0206 (5)
H31A−0.01450.82010.42330.025*
C320.07929 (16)0.7278 (4)0.38689 (8)0.0199 (5)
O1W0.18431 (15)0.4638 (4)0.27295 (7)0.0412 (6)
H1W10.21630.37230.26560.062*
H2W10.19140.59150.26550.062*
O2W0.14735 (14)0.8507 (3)0.24985 (8)0.0364 (5)
H1W20.12460.92070.26830.055*
H2W20.14970.91240.22670.055*
O3W0.04390 (14)0.3916 (3)0.22039 (7)0.0332 (5)
H1W30.02510.28050.22330.050*
H2W30.08250.42990.24110.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0148 (8)0.0239 (9)0.0195 (9)0.0007 (7)0.0003 (7)−0.0020 (7)
O20.0156 (9)0.0249 (10)0.0211 (9)0.0016 (7)−0.0020 (7)−0.0030 (7)
O30.0206 (10)0.0275 (11)0.0195 (9)−0.0027 (8)0.0004 (7)−0.0026 (8)
O40.0170 (9)0.0357 (11)0.0189 (9)−0.0007 (8)−0.0011 (7)0.0010 (8)
O50.0174 (9)0.0322 (11)0.0183 (9)−0.0007 (8)−0.0005 (7)0.0020 (8)
O60.0176 (9)0.0231 (10)0.0173 (8)0.0037 (7)0.0004 (7)0.0023 (7)
C10.0201 (12)0.0146 (12)0.0190 (12)−0.0006 (9)0.0024 (10)0.0041 (9)
C20.0212 (12)0.0183 (13)0.0197 (12)−0.0032 (10)−0.0002 (10)0.0035 (10)
C30.0307 (14)0.0204 (13)0.0150 (12)−0.0013 (11)0.0008 (10)0.0015 (10)
C40.0299 (14)0.0211 (14)0.0190 (12)0.0018 (11)0.0064 (10)0.0028 (10)
C50.0196 (12)0.0214 (13)0.0214 (12)0.0009 (10)0.0032 (10)0.0027 (10)
C60.0218 (12)0.0187 (13)0.0177 (11)0.0009 (10)0.0007 (10)0.0019 (10)
C70.0137 (12)0.0288 (15)0.0231 (13)−0.0004 (10)−0.0016 (10)0.0009 (11)
C80.0142 (12)0.0315 (15)0.0233 (13)−0.0036 (10)−0.0013 (10)0.0013 (11)
C90.0188 (13)0.0347 (16)0.0245 (14)−0.0062 (11)0.0012 (11)−0.0065 (12)
C100.0214 (13)0.0370 (16)0.0206 (13)−0.0007 (11)−0.0046 (11)−0.0049 (12)
C110.0239 (13)0.0201 (13)0.0183 (12)0.0025 (10)0.0023 (10)−0.0008 (10)
C120.0278 (14)0.0245 (14)0.0220 (13)0.0057 (11)−0.0033 (11)−0.0010 (11)
C130.0384 (17)0.0267 (15)0.0183 (13)0.0075 (12)0.0002 (11)−0.0005 (11)
C140.0355 (16)0.0268 (15)0.0208 (13)0.0038 (12)0.0078 (12)0.0041 (11)
C150.0240 (14)0.0261 (14)0.0229 (13)0.0007 (11)0.0044 (11)0.0042 (11)
C160.0257 (14)0.0215 (13)0.0180 (12)0.0028 (11)0.0010 (10)0.0015 (10)
C170.0156 (12)0.0315 (15)0.0230 (13)−0.0007 (11)0.0031 (10)0.0014 (11)
C180.0186 (13)0.0280 (14)0.0223 (13)0.0046 (11)0.0013 (10)−0.0012 (11)
C190.0160 (11)0.0225 (13)0.0218 (12)0.0021 (10)−0.0007 (10)0.0056 (10)
C200.0162 (12)0.0243 (14)0.0195 (12)−0.0027 (10)−0.0010 (10)0.0030 (10)
O70.0242 (10)0.0329 (11)0.0195 (9)0.0007 (8)0.0015 (7)0.0023 (8)
O80.0232 (11)0.0472 (14)0.0329 (11)−0.0034 (9)0.0035 (9)−0.0018 (10)
O90.0335 (12)0.0450 (14)0.0378 (12)−0.0024 (10)−0.0104 (10)−0.0134 (11)
O100.0374 (13)0.083 (2)0.0246 (11)−0.0052 (13)0.0017 (10)0.0164 (12)
O110.0358 (13)0.0645 (18)0.0381 (13)−0.0178 (12)0.0138 (10)−0.0073 (12)
O120.0249 (11)0.0551 (15)0.0399 (13)−0.0047 (10)−0.0115 (10)0.0029 (11)
O130.0362 (13)0.0625 (17)0.0207 (10)−0.0072 (11)−0.0047 (9)0.0043 (10)
N10.0214 (11)0.0278 (13)0.0261 (12)−0.0022 (9)−0.0042 (10)0.0019 (10)
N20.0242 (12)0.0275 (13)0.0302 (13)0.0034 (10)0.0071 (10)0.0011 (10)
N30.0261 (12)0.0295 (13)0.0236 (12)0.0017 (10)−0.0040 (10)−0.0014 (10)
C210.0237 (14)0.0226 (13)0.0195 (12)0.0026 (10)0.0016 (10)−0.0018 (10)
C220.0193 (12)0.0205 (13)0.0239 (13)0.0010 (10)−0.0008 (10)−0.0009 (11)
C230.0248 (13)0.0216 (13)0.0182 (12)0.0050 (11)−0.0023 (10)−0.0003 (10)
C240.0229 (13)0.0217 (14)0.0240 (13)0.0029 (11)0.0041 (11)−0.0001 (11)
C250.0188 (12)0.0240 (14)0.0256 (13)0.0037 (10)−0.0004 (10)−0.0036 (11)
C260.0213 (13)0.0247 (14)0.0209 (12)0.0037 (11)−0.0030 (10)−0.0031 (10)
O140.0263 (10)0.0257 (10)0.0257 (10)0.0009 (8)0.0046 (8)0.0024 (8)
O150.0242 (11)0.0390 (14)0.0577 (16)0.0068 (10)0.0023 (11)0.0085 (12)
O160.0276 (12)0.0609 (17)0.0435 (14)−0.0110 (11)−0.0089 (10)−0.0007 (12)
O170.0616 (17)0.0411 (14)0.0258 (11)0.0082 (12)−0.0068 (11)−0.0077 (10)
O180.0403 (13)0.0372 (13)0.0326 (11)0.0081 (10)0.0125 (10)0.0039 (10)
O190.0199 (10)0.0311 (11)0.0360 (11)−0.0020 (8)−0.0055 (9)0.0018 (9)
O200.0365 (12)0.0303 (11)0.0238 (10)0.0038 (9)−0.0043 (9)−0.0057 (9)
N40.0196 (12)0.0391 (16)0.0323 (13)−0.0040 (11)−0.0009 (10)0.0122 (12)
N50.0426 (16)0.0243 (13)0.0228 (12)0.0038 (11)0.0046 (11)0.0027 (10)
N60.0280 (12)0.0209 (12)0.0233 (11)−0.0010 (9)−0.0019 (10)0.0004 (9)
C270.0222 (13)0.0157 (12)0.0206 (12)−0.0003 (10)0.0023 (10)0.0034 (9)
C280.0196 (12)0.0232 (14)0.0239 (13)−0.0001 (10)−0.0014 (10)0.0075 (11)
C290.0287 (14)0.0239 (14)0.0210 (13)−0.0031 (11)−0.0045 (11)0.0050 (11)
C300.0272 (14)0.0183 (13)0.0195 (12)0.0023 (10)0.0012 (10)0.0028 (10)
C310.0222 (13)0.0139 (12)0.0259 (13)0.0000 (10)0.0001 (10)0.0052 (10)
C320.0200 (12)0.0182 (13)0.0214 (12)−0.0008 (10)−0.0040 (10)0.0035 (10)
O1W0.0504 (15)0.0448 (14)0.0284 (11)0.0117 (11)0.0058 (10)0.0067 (10)
O2W0.0409 (13)0.0325 (12)0.0357 (12)−0.0035 (10)0.0007 (10)0.0013 (9)
O3W0.0317 (12)0.0357 (12)0.0321 (11)−0.0066 (9)−0.0024 (9)0.0036 (10)

Geometric parameters (Å, °)

O1—C11.370 (3)C19—H19A0.97
O1—C201.429 (3)C19—H19B0.97
O2—C61.371 (3)C20—H20A0.97
O2—C71.431 (3)C20—H20B0.97
O3—C81.418 (3)O7—C211.323 (3)
O3—C91.434 (3)O7—H1O70.99
O4—C111.367 (3)O8—N11.223 (3)
O4—C101.434 (3)O9—N11.225 (3)
O5—C161.373 (3)O10—N21.214 (3)
O5—C171.435 (3)O11—N21.217 (3)
O6—C181.423 (3)O12—N31.213 (3)
O6—C191.424 (3)O13—N31.219 (3)
C1—C21.380 (4)N1—C221.474 (4)
C1—C61.412 (4)N2—C241.470 (4)
C2—C31.400 (4)N3—C261.457 (4)
C2—H2A0.93C21—C221.405 (4)
C3—C41.381 (4)C21—C261.413 (4)
C3—H3A0.93C22—C231.372 (4)
C4—C51.398 (4)C23—C241.380 (4)
C4—H4A0.93C23—H23A0.93
C5—C61.379 (4)C24—C251.370 (4)
C5—H5A0.93C25—C261.389 (4)
C7—C81.499 (4)C25—H25A0.93
C7—H7A0.97O14—C271.317 (3)
C7—H7B0.97O14—H14B0.78
C8—H8A0.97O15—N41.216 (4)
C8—H8B0.97O16—N41.225 (4)
C9—C101.499 (4)O17—N51.228 (4)
C9—H9A0.97O18—N51.216 (3)
C9—H9B0.97O19—N61.221 (3)
C10—H10A0.97O20—N61.234 (3)
C10—H10B0.97N4—C281.480 (4)
C11—C121.392 (4)N5—C301.462 (4)
C11—C161.400 (4)N6—C321.465 (4)
C12—C131.401 (4)C27—C321.407 (4)
C12—H12A0.93C27—C281.412 (4)
C13—C141.368 (4)C28—C291.368 (4)
C13—H13A0.93C29—C301.383 (4)
C14—C151.388 (4)C29—H29A0.93
C14—H14A0.93C30—C311.376 (4)
C15—C161.388 (4)C31—C321.385 (4)
C15—H15A0.93C31—H31A0.93
C17—C181.498 (4)O1W—H1W10.86
C17—H17A0.97O1W—H2W10.94
C17—H17B0.97O2W—H1W20.85
C18—H18A0.97O2W—H2W20.85
C18—H18B0.97O3W—H1W30.85
C19—C201.498 (4)O3W—H2W30.95
C1—O1—C20117.1 (2)O6—C18—H18B109.4
C6—O2—C7116.1 (2)C17—C18—H18B109.4
C8—O3—C9110.0 (2)H18A—C18—H18B108.0
C11—O4—C10117.6 (2)O6—C19—C20110.5 (2)
C16—O5—C17116.5 (2)O6—C19—H19A109.5
C18—O6—C19109.43 (19)C20—C19—H19A109.5
O1—C1—C2125.3 (2)O6—C19—H19B109.5
O1—C1—C6114.6 (2)C20—C19—H19B109.5
C2—C1—C6120.1 (2)H19A—C19—H19B108.1
C1—C2—C3120.0 (2)O1—C20—C19107.4 (2)
C1—C2—H2A120.0O1—C20—H20A110.2
C3—C2—H2A120.0C19—C20—H20A110.2
C4—C3—C2120.0 (3)O1—C20—H20B110.2
C4—C3—H3A120.0C19—C20—H20B110.2
C2—C3—H3A120.0H20A—C20—H20B108.5
C3—C4—C5120.1 (3)C21—O7—H1O7107.2
C3—C4—H4A120.0O8—N1—O9125.1 (2)
C5—C4—H4A120.0O8—N1—C22117.6 (2)
C6—C5—C4120.3 (3)O9—N1—C22117.2 (2)
C6—C5—H5A119.8O10—N2—O11124.3 (3)
C4—C5—H5A119.8O10—N2—C24117.8 (2)
O2—C6—C5125.4 (2)O11—N2—C24117.9 (2)
O2—C6—C1115.1 (2)O12—N3—O13123.5 (2)
C5—C6—C1119.5 (2)O12—N3—C26118.5 (2)
O2—C7—C8108.3 (2)O13—N3—C26118.0 (2)
O2—C7—H7A110.0O7—C21—C22117.2 (2)
C8—C7—H7A110.0O7—C21—C26128.3 (2)
O2—C7—H7B110.0C22—C21—C26114.5 (2)
C8—C7—H7B110.0C23—C22—C21124.4 (2)
H7A—C7—H7B108.4C23—C22—N1117.1 (2)
O3—C8—C7110.6 (2)C21—C22—N1118.5 (2)
O3—C8—H8A109.5C22—C23—C24117.6 (3)
C7—C8—H8A109.5C22—C23—H23A121.2
O3—C8—H8B109.5C24—C23—H23A121.2
C7—C8—H8B109.5C25—C24—C23122.3 (3)
H8A—C8—H8B108.1C25—C24—N2119.1 (2)
O3—C9—C10109.6 (2)C23—C24—N2118.6 (2)
O3—C9—H9A109.7C24—C25—C26118.4 (3)
C10—C9—H9A109.7C24—C25—H25A120.8
O3—C9—H9B109.7C26—C25—H25A120.8
C10—C9—H9B109.7C25—C26—C21122.8 (2)
H9A—C9—H9B108.2C25—C26—N3116.5 (2)
O4—C10—C9107.1 (2)C21—C26—N3120.8 (2)
O4—C10—H10A110.3C27—O14—H14B117.3
C9—C10—H10A110.3O15—N4—O16124.6 (3)
O4—C10—H10B110.3O15—N4—C28118.9 (3)
C9—C10—H10B110.3O16—N4—C28116.5 (3)
H10A—C10—H10B108.6O18—N5—O17124.1 (3)
O4—C11—C12125.0 (3)O18—N5—C30117.9 (3)
O4—C11—C16115.1 (2)O17—N5—C30118.0 (3)
C12—C11—C16119.9 (2)O19—N6—O20123.3 (2)
C11—C12—C13119.3 (3)O19—N6—C32118.6 (2)
C11—C12—H12A120.3O20—N6—C32118.0 (2)
C13—C12—H12A120.3O14—C27—C32126.7 (2)
C14—C13—C12120.3 (3)O14—C27—C28118.7 (2)
C14—C13—H13A119.8C32—C27—C28114.6 (2)
C12—C13—H13A119.8C29—C28—C27123.2 (3)
C13—C14—C15120.8 (3)C29—C28—N4116.8 (2)
C13—C14—H14A119.6C27—C28—N4120.0 (2)
C15—C14—H14A119.6C28—C29—C30119.0 (3)
C16—C15—C14119.8 (3)C28—C29—H29A120.5
C16—C15—H15A120.1C30—C29—H29A120.5
C14—C15—H15A120.1C31—C30—C29121.5 (3)
O5—C16—C15125.1 (3)C31—C30—N5119.0 (3)
O5—C16—C11115.0 (2)C29—C30—N5119.5 (2)
C15—C16—C11119.8 (2)C30—C31—C32118.0 (3)
O5—C17—C18107.5 (2)C30—C31—H31A121.0
O5—C17—H17A110.2C32—C31—H31A121.0
C18—C17—H17A110.2C31—C32—C27123.6 (2)
O5—C17—H17B110.2C31—C32—N6115.5 (2)
C18—C17—H17B110.2C27—C32—N6120.9 (2)
H17A—C17—H17B108.5H1W1—O1W—H2W1125.3
O6—C18—C17111.0 (2)H1W2—O2W—H2W2107.7
O6—C18—H18A109.4H1W3—O3W—H2W3115.7
C17—C18—H18A109.4
C20—O1—C1—C2−9.1 (4)O9—N1—C22—C21−128.6 (3)
C20—O1—C1—C6173.1 (2)C21—C22—C23—C24−3.3 (4)
O1—C1—C2—C3−178.6 (2)N1—C22—C23—C24178.4 (2)
C6—C1—C2—C3−1.0 (4)C22—C23—C24—C251.4 (4)
C1—C2—C3—C40.1 (4)C22—C23—C24—N2−179.3 (2)
C2—C3—C4—C50.7 (4)O10—N2—C24—C25171.8 (3)
C3—C4—C5—C6−0.6 (4)O11—N2—C24—C25−8.1 (4)
C7—O2—C6—C57.2 (4)O10—N2—C24—C23−7.6 (4)
C7—O2—C6—C1−175.0 (2)O11—N2—C24—C23172.5 (3)
C4—C5—C6—O2177.4 (3)C23—C24—C25—C260.5 (4)
C4—C5—C6—C1−0.3 (4)N2—C24—C25—C26−178.8 (2)
O1—C1—C6—O21.1 (3)C24—C25—C26—C21−0.7 (4)
C2—C1—C6—O2−176.8 (2)C24—C25—C26—N3178.2 (3)
O1—C1—C6—C5179.0 (2)O7—C21—C26—C25178.3 (3)
C2—C1—C6—C51.1 (4)C22—C21—C26—C25−0.9 (4)
C6—O2—C7—C8−173.3 (2)O7—C21—C26—N3−0.6 (4)
C9—O3—C8—C7174.3 (2)C22—C21—C26—N3−179.8 (2)
O2—C7—C8—O3−73.2 (3)O12—N3—C26—C255.1 (4)
C8—O3—C9—C10179.1 (2)O13—N3—C26—C25−173.7 (3)
C11—O4—C10—C9175.4 (2)O12—N3—C26—C21−175.9 (3)
O3—C9—C10—O471.5 (3)O13—N3—C26—C215.3 (4)
C10—O4—C11—C12−8.7 (4)O14—C27—C28—C29177.0 (3)
C10—O4—C11—C16173.5 (2)C32—C27—C28—C29−2.1 (4)
O4—C11—C12—C13−176.6 (3)O14—C27—C28—N4−4.0 (4)
C16—C11—C12—C131.1 (4)C32—C27—C28—N4176.8 (2)
C11—C12—C13—C14−0.5 (4)O15—N4—C28—C29146.4 (3)
C12—C13—C14—C15−0.3 (5)O16—N4—C28—C29−32.1 (4)
C13—C14—C15—C160.5 (5)O15—N4—C28—C27−32.6 (4)
C17—O5—C16—C15−2.1 (4)O16—N4—C28—C27148.9 (3)
C17—O5—C16—C11175.8 (2)C27—C28—C29—C302.6 (4)
C14—C15—C16—O5177.9 (3)N4—C28—C29—C30−176.4 (2)
C14—C15—C16—C110.1 (4)C28—C29—C30—C31−1.1 (4)
O4—C11—C16—O5−1.0 (3)C28—C29—C30—N5−179.7 (2)
C12—C11—C16—O5−178.9 (2)O18—N5—C30—C314.1 (4)
O4—C11—C16—C15177.0 (2)O17—N5—C30—C31−175.3 (3)
C12—C11—C16—C15−0.9 (4)O18—N5—C30—C29−177.2 (3)
C16—O5—C17—C18−166.7 (2)O17—N5—C30—C293.4 (4)
C19—O6—C18—C17176.9 (2)C29—C30—C31—C32−0.7 (4)
O5—C17—C18—O6−69.8 (3)N5—C30—C31—C32177.9 (2)
C18—O6—C19—C20−177.3 (2)C30—C31—C32—C271.2 (4)
C1—O1—C20—C19179.0 (2)C30—C31—C32—N6178.9 (2)
O6—C19—C20—O172.0 (3)O14—C27—C32—C31−178.9 (3)
O7—C21—C22—C23−176.3 (3)C28—C27—C32—C310.2 (4)
C26—C21—C22—C233.0 (4)O14—C27—C32—N63.6 (4)
O7—C21—C22—N12.0 (4)C28—C27—C32—N6−177.4 (2)
C26—C21—C22—N1−178.7 (2)O19—N6—C32—C310.9 (4)
O8—N1—C22—C23−128.7 (3)O20—N6—C32—C31−178.9 (2)
O9—N1—C22—C2349.9 (4)O19—N6—C32—C27178.6 (2)
O8—N1—C22—C2152.9 (4)O20—N6—C32—C27−1.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H1O7···O3W1.001.922.618 (3)124
O7—H1O7···O131.001.842.664 (3)138
O7—H1O7···N31.002.492.985 (3)110
O1W—H1W1···O60.872.142.978 (3)162
O1W—H2W1···O2W0.942.032.900 (4)152
O2W—H1W2···O1i0.852.563.215 (3)135
O2W—H1W2···O2i0.852.453.265 (3)162
O2W—H2W2···O4i0.852.423.198 (3)152
O2W—H2W2···O5i0.852.433.155 (3)144
O3W—H1W3···O30.852.022.861 (3)173
O3W—H2W3···O1W0.951.962.881 (3)163
O14—H14B···O1W0.782.062.732 (3)144
O14—H14B···O200.782.052.632 (3)131
C3—H3A···O11ii0.932.603.323 (4)136
C7—H7A···O6iii0.972.583.393 (3)142
C7—H7B···O19iv0.972.593.135 (4)116
C9—H9A···O12iii0.972.393.341 (4)165
C19—H19A···O19v0.972.533.301 (3)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2617).

References

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