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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m463–m464.
Published online 2010 March 27. doi:  10.1107/S160053681001086X
PMCID: PMC2983962

(2,6-Bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thia­diazol-5-yl)diazen­yl]-1H-pyrazol-1-yl}-4-oxo-1,4-dihydro-1,3,5-triazin-1-ido)methanol(phenol)sodium phenol tetra­solvate

Abstract

The title compound, [Na(C23H28N17OS2)(CH3OH)(C6H5OH)]·4C6H5OH, is a five-coordinate NaI complex. The Na+ cation is bound to three N atoms of the triazinide ligand, two from each pyrazole ring and one from the central deprotonated triazine ring system. O atoms from a methanol and a phenol mol­ecule complete the five-coordinate NaN3O2 coordination environment. The asymmetric unit also includes three complete and two half phenol mol­ecules, four of which are hydrogen bonded to the N atoms of the thia­diazole ring. Two of the phenol solvent mol­ecules are disordered over two discrete inversion centres. The triazinide ligand is essentially planar (mean deviation from the least-squares plane = 0.0524 Å), with the methyl groups of the tert-butyl substituents on the pyrazole rings located above and below the plane. The planarity of this system is further assisted by the formation of four intra­molecular N—H(...)N hydrogen bonds between the N—H bonds of both amino groups on the pyrazole rings and the N atoms of the triazine ring and also from each of the adjacent diazene (–N=N–) bonds. The highly polar mol­ecules are stacked along the a axis through the central Na atom sandwiched by two kinds of alternating inter­molecular hydrogen bonds: O(carbon­yl)(...)H—O(methanol)/Na/O—H(phenol)(...)O(carbon­yl). These inter­actions form two polymer chains per mol­ecule.

Related literature

For details of azo pigments, see: Herbst & Hunger (2004 [triangle]). For the synthesis of the title compound, see: Nagata & Tateishi (2009 [triangle]). For the structures of other azo complexes with five-coordinate Na+, see: Mizuguchi et al. (2007 [triangle]); Sato, Shibata et al. (2008 [triangle]); Sato, Uta et al. (2008 [triangle]). For the structure of a related ligand, see: Shibata & Mizuguchi (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m463-scheme1.jpg

Experimental

Crystal data

  • [Na(C23H28N17OS2)(CH4O)(C6H6O)]·4C6H6O
  • M r = 1148.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m463-efi1.jpg
  • a = 8.38964 (15) Å
  • b = 18.8780 (3) Å
  • c = 20.4060 (4) Å
  • α = 114.103 (1)°
  • β = 96.580 (1)°
  • γ = 95.650 (1)°
  • V = 2892.83 (9) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 1.46 mm−1
  • T = 93 K
  • 0.50 × 0.30 × 0.20 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.345, T max = 0.748
  • 32979 measured reflections
  • 10340 independent reflections
  • 7267 reflections with I > 2σ(I 2)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.196
  • S = 0.99
  • 10340 reflections
  • 819 parameters
  • 156 restraints
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006 [triangle]); program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2006 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001086X/sj2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001086X/sj2750Isup2.hkl

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

supplementary crystallographic information

Comment

Azo pigments are widely used in imaging and painting industries because of their versatile colors, high tinctorial strength as well as their low price (Herbst & Hunger, 2004). Some novel azo pigments have recently been reported by Nagata et al. (2009) which include 2,6-bis[5-amino-3-tert-butyl-4-(3-methyl-1,2,4-thiadiazol-5-yldiazenyl)-1H-pyrazol-1-yl]-1,3,5-triazin-4(1H)-one (i.e. Na-free compound of the title compound with one additional H atom at the N atom of the triazine one). In the course of our structural studies on this compound, however, we have isolated two kinds of single crystals from the reaction product: bis-azo and mono-azo compounds. To our surprise, the former is found to include a NaI-atom as the central metal (i.e. the title compound); whereas the latter is a NaI-free mono-azo compound. In the synthesis of azo pigments, it is quite common to use sodium nitrite for the preparation of diazonium salts. However, the inclusion of Na in the final product has not been reported to date. This paper deals with the structure of the NaI-containing bis-azo compound, while the NaI-free mono-azo compound will be reported elsewhere (Shibata & Mizuguchi, 2010).

The title compound, C30H38N17NaO3S2.4(C6H6O), is a five-coordinate Na-bisazo complex, comprising as ligands two N atoms of each pyrazol ring and one N atom of the central triazine one as well as two O atoms of the solvent molecules: one methanol and one phenol. Fig. 1 shows the ORTEP plot of I. The asymmetric unit also includes three full phenol molecules (C30—C35/O3, C36—C41/O4, and C42—C47/O5) and two half molecules (C48—C50/O6 and C51—C53/O7). In four of these molecules, the O—H group of the molecule is hydrogen-bonded to the N atom of the 1,2,4-thiadiazol ring (N1, N2, N14, and N15) through O—H···N hydrogen bonds. On the other hand, the fifth phenol molecule (C48—C50/O6) remains free. There are four N—H···N intramolecular hydrogen bonds formed between the N—H of the amino group of the pyrazol ring and the N atom of the azo bond: N16—H16M···N3, N16—H16N···N9, N17—H17M···N13, and N17—H17N···N8. It is remarkable to note that the central Na atom bridges two monoazo moieties in a cis fashion to make the molecule entirely flat (mean deviation from the least-squares plane with a methyl group from the t-butyl substituent on the pyrazol ring above and below that plane: 0.0524 Å). Additionally, the four intramolecular N—H···N hydrogen bonds also contribute to the planarity of the system. The occurrence of the cis form is quite unusual, because the trans form of the Na-free structure as formed by free rotation around C7—N6 or C9—N10 is more stable according to molecular orbital calculations. However, the Na-coordination appears here to be the driving force to form the cis structure.

The incorporation of the NaI cation to form a complex is due largely to the formation of strong Na—N bonds as shown by the distances Na1—N5 = 2.644 (3), Na1—N7 = 2.420 (3), and Na1—N11 = 2.642 (3) Å. The Na1—N5 and Na1—N11 distances are nearly equal, as indicated by the fact that the angles N5–Na1–N7 and N7–Na1–N11 are closely similar at 65.04 (8) and 65.51 (8)°, respectively. Furthermore, the O atoms of a phenol and methanol molecule are also coordinated to the Na atom, Na1—O2 = 2.437 (2) and Na1—O8 = 2.336 (3) Å, respectively generating a five-coordinate NaI-bis-azo complex. Similar five-coordinate NaI-complexes are found in other azo compounds (Mizuguchi et al., 2007; Sato, Shibata et al., 2008; Sato, Uta et al., 2008). The azo bond in this molecule is also noteworthy. The bond lengths, N3—N4 and N12—N13 are 1.295 (4) and 1.308 (3) Å, respectively. These are longer than the standard N=N bond of about 1.24 Å, found in other bis-azo compounds (Mizuguchi et al., 2007;Sato, Uta et al., 2008).

Fig. 2 illustrates the molecular stack along the a axis. The methanol and phenol ligands to the Na atom are positioned above and below the bis-azo skeleton. The polar bis-azo molecules are arranged alternately in such a way as to effectively cancel their dipole moments to lower the lattice energy. In addition, two stacked columns are formed composed of the central NaI atom sandwiched by alternating two kinds of intermolecular hydrogen bonds: O (carbonyl oxygen: O1ii)···O—H (methanol: O8)/Na1/O—H (phenol: O2)···O (carbonyl oxygen: O1i)(Fig. 2). This forms two one-dimensional polymer-chains per molecule and assures a high thermal-stability of the compound.

Experimental

The title compound was synthesized as described by Nagata et al. (2009). The structure reported here is of the NaI complex product which made up approximately 80% of the product mixture according by emission spectrochemical analysis. A single crystal suitable for X-ray analysis was grown from a mixed solvent of methanol and phenol (1:1 in molar ratio) prepared at 80 °C. Needle shaped crystals were obtained in a closed system saturated with methanol vapor after standing for one week.

Refinement

The C atoms of the phenol molecule which acts as a ligand to the Na atom were disordered over two positions (C24—C29 and C24A—C29A) with occupancies of 0.786 (6)/0.214 (6), respectively. The entire molecule of another phenol was disordered over two sites (C42—C47/O5 and C42A—C47A/O5A) with occupancies of 0.750 (5) and 0.250 (5), respectively. The benzene rings of these disordered phenol molecules were refined anisotropically as rigid groups. The two half phenol-molecules were disordered about a center of symmetry (C48—C50/O6 and C51—C53/O7) with an occupancy of 0.5. Because of this disorder, there is a discrepancy between the H atom counts in the_chemical_formula_sum and the formula from the_atom_site data: one H atom is missing. The occupancies of all disorders described above extend to the associated H atoms. All H atoms were placed in geometrically idealized position and constrained to ride on their parent atoms, with C—H = 0.95, and 0.98 Å, and Uiso(H) = 1.2 and 1.5 Ueq(C), respectively, and with O—H = 0.84, and N—H = 0.88Å and Uiso(H) = 1.2.

Figures

Fig. 1.
ORTEP plot of I. Hydrogen atoms except for those involved in hydrogen bonds (dotted lines) are omitted for clarity. Symmetry codes: (i) -x+1, -y+2, -z+1 and (ii) -x-1, -y-1, -z.
Fig. 2.
The molecular stack along <100>. Symmetry codes: (i) -x, -y, -z and (ii) -x-1, -y,-z.

Crystal data

[Na(C23H28N17OS2)(CH4O)(C6H6O)]·4C6H6OZ = 2
Mr = 1148.30F(000) = 1208.00
Triclinic, P1Dx = 1.318 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 8.38964 (15) ÅCell parameters from 26974 reflections
b = 18.8780 (3) Åθ = 4.2–68.2°
c = 20.4060 (4) ŵ = 1.46 mm1
α = 114.103 (1)°T = 93 K
β = 96.580 (1)°Needle, yellow
γ = 95.650 (1)°0.50 × 0.30 × 0.20 mm
V = 2892.83 (9) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer7267 reflections with F2 > 2σ(F2)
ω scansRint = 0.054
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)θmax = 68.2°
Tmin = 0.345, Tmax = 0.748h = −9→9
32979 measured reflectionsk = −20→22
10340 independent reflectionsl = −24→24

Refinement

Refinement on F2156 restraints
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.196w = 1/[σ2(Fo2) + (0.101P)2 + 2.2948P] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
10340 reflectionsΔρmax = 0.66 e Å3
819 parametersΔρmin = −0.47 e Å3

Special details

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 > 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*/UeqOcc. (<1)
S11.47119 (10)0.92371 (4)0.62076 (4)0.0412 (2)
S2−0.01553 (10)0.09004 (5)0.26699 (4)0.0442 (2)
Na10.70228 (15)0.50735 (7)0.35073 (6)0.0382 (3)
O10.8097 (3)0.48489 (11)0.65787 (10)0.0342 (5)
O20.8888 (3)0.45383 (13)0.26640 (11)0.0428 (5)
H2O0.98060.47410.29260.051*
O31.8364 (3)1.11563 (15)0.72119 (14)0.0583 (7)
H3O1.75531.08050.70990.070*
O4−0.3653 (3)−0.08841 (19)0.18027 (15)0.0843 (11)
H4O−0.2885−0.06830.21580.101*
O61.2701 (9)1.3726 (4)0.9187 (4)0.104 (2)0.50
H6O1.26901.33650.93280.124*0.50
O70.3015 (6)0.1073 (2)0.5196 (2)0.0435 (11)0.50
H7O0.21900.08950.48670.052*0.50
O80.4989 (3)0.57323 (15)0.32562 (14)0.0543 (7)
H8O0.40840.55900.33410.065*
N11.5988 (3)0.98531 (15)0.69533 (16)0.0435 (7)
N21.4734 (3)0.89848 (15)0.73354 (15)0.0423 (6)
N31.2860 (3)0.80306 (14)0.63605 (14)0.0389 (6)
N41.2247 (3)0.78470 (14)0.56894 (14)0.0367 (6)
N50.9211 (3)0.62032 (14)0.45304 (13)0.0359 (6)
N60.9431 (3)0.61113 (13)0.51868 (13)0.0318 (6)
N70.7394 (3)0.50109 (14)0.46751 (13)0.0322 (6)
N80.6688 (3)0.43844 (14)0.54359 (13)0.0329 (6)
N90.8837 (3)0.54727 (14)0.58893 (13)0.0321 (6)
N100.5377 (3)0.39052 (14)0.42586 (13)0.0333 (6)
N110.5108 (3)0.39071 (15)0.35605 (13)0.0349 (6)
N120.2410 (3)0.22050 (14)0.33247 (13)0.0354 (6)
N130.2218 (3)0.19251 (14)0.38056 (13)0.0356 (6)
N14−0.1125 (4)0.01872 (16)0.28168 (16)0.0488 (7)
N150.0696 (3)0.08488 (14)0.38837 (14)0.0373 (6)
N161.1016 (3)0.67754 (15)0.63825 (13)0.0378 (6)
H16N1.05880.64220.65170.045*
H16M1.17480.71740.66920.045*
N170.4406 (3)0.31137 (15)0.48461 (13)0.0369 (6)
H17N0.50250.34230.52660.044*
H17M0.37620.26950.48050.044*
C11.6865 (5)1.0074 (2)0.8222 (2)0.0545 (9)
H1A1.76241.05010.82190.082*
H1B1.74780.97150.83440.082*
H1C1.61691.02930.85860.082*
C21.5832 (4)0.96327 (19)0.74835 (19)0.0444 (8)
C31.4027 (4)0.87033 (17)0.66531 (18)0.0386 (7)
C41.1104 (4)0.71951 (16)0.53837 (16)0.0345 (7)
C51.0559 (4)0.67071 (16)0.57146 (16)0.0320 (7)
C61.0198 (4)0.68461 (16)0.46545 (17)0.0361 (7)
C70.8499 (4)0.54981 (16)0.52534 (16)0.0310 (6)
C80.7878 (4)0.49012 (16)0.59835 (16)0.0314 (6)
C90.6561 (4)0.44673 (17)0.48198 (15)0.0310 (6)
C100.4443 (4)0.32788 (17)0.42756 (16)0.0333 (7)
C110.3520 (4)0.28622 (17)0.35716 (16)0.0349 (7)
C120.3997 (4)0.32902 (18)0.31600 (16)0.0353 (7)
C130.1050 (4)0.12619 (17)0.35169 (16)0.0346 (7)
C14−0.0544 (4)0.02450 (18)0.34631 (18)0.0400 (7)
C15−0.1193 (5)−0.0316 (2)0.3746 (2)0.0545 (9)
H15A−0.2214−0.06310.34320.082*
H15B−0.1393−0.00230.42430.082*
H15C−0.0401−0.06630.37500.082*
C161.0319 (5)0.71468 (17)0.40775 (17)0.0436 (8)
C171.2056 (5)0.7151 (2)0.3907 (2)0.0552 (10)
H17A1.28260.74920.43510.083*
H17B1.21400.73480.35340.083*
H17C1.23100.66150.37270.083*
C180.9917 (6)0.79872 (19)0.4363 (2)0.0580 (10)
H18A0.88260.79860.44900.087*
H18B0.99570.81790.39840.087*
H18C1.07130.83320.47960.087*
C190.9102 (5)0.6628 (2)0.33927 (19)0.0579 (11)
H19A0.93410.60900.32050.087*
H19B0.91810.68300.30230.087*
H19C0.80000.66310.35080.087*
C200.3341 (4)0.30941 (19)0.23735 (16)0.0389 (7)
C210.3634 (6)0.2270 (2)0.18819 (19)0.0658 (12)
H21A0.48050.22680.18930.099*
H21B0.30970.21220.13810.099*
H21C0.31890.18930.20570.099*
C220.4140 (5)0.3709 (2)0.21546 (19)0.0547 (10)
H22A0.39120.42290.24680.082*
H22B0.37030.35790.16460.082*
H22C0.53170.37140.22100.082*
C230.1522 (4)0.3110 (2)0.22894 (17)0.0441 (8)
H23A0.09760.27010.24030.066*
H23B0.11010.30130.17870.066*
H23C0.13170.36250.26240.066*
C240.9025 (5)0.43178 (19)0.19536 (13)0.0392 (13)0.786 (6)
C250.8044 (4)0.36536 (19)0.14096 (16)0.0517 (13)0.786 (6)
H250.72700.33470.15330.062*0.786 (6)
C260.8195 (4)0.34377 (19)0.06846 (14)0.0626 (15)0.786 (6)
H260.75250.29840.03130.075*0.786 (6)
C270.9327 (5)0.3886 (2)0.05035 (16)0.0588 (15)0.786 (6)
H270.94310.37390.00080.071*0.786 (6)
C281.0308 (5)0.4550 (2)0.1048 (2)0.0534 (15)0.786 (6)
H281.10810.48570.09240.064*0.786 (6)
C291.0156 (5)0.47662 (17)0.1773 (2)0.0456 (14)0.786 (6)
H291.08270.52200.21440.055*0.786 (6)
C24A0.9176 (15)0.4523 (8)0.1933 (5)0.033 (4)0.214 (6)
C25A0.7821 (11)0.4243 (8)0.1384 (5)0.045 (4)0.214 (6)
H25A0.67740.41450.14930.054*0.214 (6)
C26A0.7998 (12)0.4108 (7)0.0676 (5)0.050 (4)0.214 (6)
H26A0.70720.39170.03000.060*0.214 (6)
C27A0.9531 (15)0.4252 (7)0.0516 (6)0.044 (4)0.214 (6)
H27A0.96520.41600.00320.053*0.214 (6)
C28A1.0885 (11)0.4532 (8)0.1065 (8)0.037 (4)0.214 (6)
H28A1.19330.46310.09560.044*0.214 (6)
C29A1.0708 (12)0.4667 (8)0.1773 (7)0.032 (4)0.214 (6)
H29A1.16340.48580.21480.039*0.214 (6)
C301.7987 (5)1.1878 (2)0.7660 (2)0.0549 (10)
C311.9181 (6)1.2527 (2)0.7902 (2)0.0623 (11)
H312.02161.24770.77560.075*
C321.8840 (7)1.3265 (2)0.8368 (2)0.0718 (14)
H321.96671.37120.85500.086*
C331.7335 (8)1.3350 (3)0.8566 (3)0.0808 (15)
H331.71131.38530.88710.097*
C341.6159 (7)1.2702 (3)0.8321 (3)0.0838 (15)
H341.51171.27550.84580.101*
C351.6479 (6)1.1958 (3)0.7868 (3)0.0762 (13)
H351.56591.15100.77030.091*
C36−0.3128 (4)−0.1420 (2)0.1217 (2)0.0550 (10)
C37−0.4253 (5)−0.1824 (3)0.0581 (2)0.0708 (13)
H37−0.5345−0.17290.05670.085*
C38−0.3786 (5)−0.2362 (2)−0.0028 (2)0.0577 (10)
H38−0.4548−0.2624−0.04670.069*
C39−0.2229 (5)−0.2522 (2)−0.00060 (18)0.0497 (9)
H39−0.1909−0.2896−0.04260.060*
C40−0.1127 (5)−0.2129 (2)0.06386 (18)0.0479 (8)
H40−0.0050−0.22420.06610.057*
C41−0.1577 (4)−0.15748 (19)0.12469 (18)0.0435 (8)
H41−0.0810−0.13030.16840.052*
O51.2733 (5)0.8315 (3)0.8091 (3)0.0608 (12)0.750 (5)
H5O1.32430.85540.78910.073*0.750 (5)
C421.2431 (6)0.8841 (2)0.87364 (18)0.0589 (16)0.750 (5)
C431.1592 (6)0.85495 (18)0.9146 (2)0.0800 (19)0.750 (5)
H431.12810.79980.89780.096*0.750 (5)
C441.1207 (7)0.9064 (3)0.9800 (2)0.107 (2)0.750 (5)
H441.06330.88641.00800.128*0.750 (5)
C451.1662 (7)0.9870 (2)1.0046 (2)0.115 (3)0.750 (5)
H451.13991.02211.04930.138*0.750 (5)
C461.2501 (7)1.01619 (17)0.9636 (2)0.103 (2)0.750 (5)
H461.28121.07130.98040.123*0.750 (5)
C471.2886 (5)0.9648 (2)0.8982 (2)0.0742 (17)0.750 (5)
H471.34600.98470.87020.089*0.750 (5)
O5A1.2908 (14)0.7925 (7)0.7733 (6)0.046 (3)0.250 (5)
H5OA1.32610.82880.76240.055*0.250 (5)
C42A1.2674 (13)0.8238 (6)0.8441 (4)0.042 (3)0.250 (5)
C43A1.2089 (12)0.7696 (5)0.8690 (4)0.044 (3)0.250 (5)
H43A1.19230.71490.83800.053*0.250 (5)
C44A1.1747 (12)0.7953 (6)0.9394 (5)0.059 (4)0.250 (5)
H44A1.13470.75830.95640.070*0.250 (5)
C45A1.1989 (14)0.8753 (7)0.9848 (4)0.072 (4)0.250 (5)
H45A1.17550.89291.03290.086*0.250 (5)
C46A1.2575 (14)0.9295 (5)0.9598 (5)0.073 (4)0.250 (5)
H46A1.27410.98410.99090.088*0.250 (5)
C47A1.2917 (14)0.9038 (5)0.8895 (6)0.059 (4)0.250 (5)
H47A1.33170.94080.87240.071*0.250 (5)
C481.3808 (7)1.4337 (3)0.9641 (5)0.107 (2)
C491.3945 (9)1.4900 (4)0.9377 (4)0.123 (2)
H491.32341.48470.89570.148*
C501.4826 (9)1.4444 (4)1.0249 (4)0.119 (2)
H501.47051.40571.04330.143*
C510.3909 (5)0.0526 (2)0.5112 (2)0.0512 (9)
C520.3499 (5)−0.0221 (2)0.4556 (2)0.0505 (9)
H520.2458−0.03760.42560.061*
C530.4588 (5)−0.0747 (2)0.4431 (2)0.0511 (9)
H530.4315−0.12540.40360.061*
C540.4742 (6)0.5906 (4)0.2625 (3)0.0928 (18)
H54A0.57980.60230.24970.139*
H54B0.41800.63630.27380.139*
H54C0.40830.54510.22130.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0477 (5)0.0303 (4)0.0446 (5)0.0054 (3)0.0105 (4)0.0144 (3)
S20.0453 (5)0.0398 (4)0.0356 (4)0.0109 (4)−0.0028 (3)0.0058 (3)
Na10.0423 (7)0.0411 (7)0.0361 (7)0.0094 (5)0.0071 (5)0.0206 (5)
O10.0411 (12)0.0334 (11)0.0301 (11)0.0062 (9)0.0051 (9)0.0157 (9)
O20.0402 (13)0.0472 (13)0.0325 (12)0.0089 (10)0.0005 (9)0.0094 (10)
O30.0552 (16)0.0481 (14)0.0577 (16)−0.0048 (12)0.0098 (13)0.0116 (12)
O40.0449 (16)0.095 (2)0.0560 (17)0.0093 (15)0.0047 (13)−0.0235 (16)
O60.094 (5)0.077 (5)0.149 (7)−0.007 (4)−0.009 (5)0.070 (5)
O70.047 (3)0.040 (2)0.037 (2)0.008 (2)−0.005 (2)0.012 (2)
O80.0424 (14)0.0757 (17)0.0714 (17)0.0151 (12)0.0148 (12)0.0550 (15)
N10.0406 (16)0.0363 (14)0.0507 (17)0.0072 (12)0.0099 (13)0.0147 (13)
N20.0465 (17)0.0359 (14)0.0449 (16)0.0109 (12)0.0066 (13)0.0169 (13)
N30.0461 (17)0.0299 (13)0.0410 (15)0.0116 (12)0.0108 (12)0.0134 (12)
N40.0473 (16)0.0243 (12)0.0393 (15)0.0108 (11)0.0133 (12)0.0119 (11)
N50.0536 (17)0.0288 (13)0.0306 (13)0.0106 (12)0.0109 (12)0.0159 (11)
N60.0426 (15)0.0285 (12)0.0279 (13)0.0064 (11)0.0068 (11)0.0152 (10)
N70.0392 (15)0.0299 (13)0.0307 (13)0.0095 (11)0.0081 (11)0.0146 (11)
N80.0370 (14)0.0331 (13)0.0288 (13)0.0060 (11)0.0048 (11)0.0135 (11)
N90.0390 (15)0.0301 (13)0.0301 (13)0.0061 (11)0.0059 (11)0.0157 (11)
N100.0374 (15)0.0373 (14)0.0267 (13)0.0049 (11)0.0024 (10)0.0162 (11)
N110.0380 (15)0.0417 (14)0.0291 (13)0.0112 (12)0.0061 (11)0.0179 (12)
N120.0389 (15)0.0342 (13)0.0340 (14)0.0131 (11)0.0088 (11)0.0132 (11)
N130.0374 (15)0.0336 (13)0.0321 (13)0.0069 (11)0.0039 (11)0.0106 (11)
N140.0481 (18)0.0370 (15)0.0480 (17)0.0084 (13)0.0013 (14)0.0062 (13)
N150.0391 (15)0.0313 (13)0.0366 (14)0.0071 (11)0.0075 (11)0.0091 (11)
N160.0476 (16)0.0338 (14)0.0327 (14)0.0035 (12)0.0073 (12)0.0153 (11)
N170.0428 (16)0.0368 (14)0.0310 (13)−0.0010 (12)0.0028 (11)0.0168 (11)
C10.047 (2)0.058 (2)0.049 (2)0.0053 (18)0.0004 (17)0.0158 (18)
C20.0398 (19)0.0398 (18)0.052 (2)0.0141 (15)0.0100 (16)0.0152 (16)
C30.0414 (19)0.0273 (15)0.0457 (19)0.0118 (13)0.0092 (15)0.0123 (14)
C40.051 (2)0.0229 (14)0.0346 (16)0.0120 (13)0.0141 (14)0.0138 (12)
C50.0391 (17)0.0250 (14)0.0326 (16)0.0099 (12)0.0100 (13)0.0109 (12)
C60.053 (2)0.0245 (14)0.0361 (17)0.0128 (13)0.0157 (14)0.0141 (13)
C70.0378 (17)0.0276 (14)0.0322 (15)0.0124 (13)0.0100 (13)0.0149 (12)
C80.0374 (17)0.0283 (14)0.0305 (15)0.0098 (12)0.0073 (12)0.0131 (12)
C90.0305 (16)0.0340 (15)0.0302 (15)0.0090 (13)0.0054 (12)0.0143 (13)
C100.0339 (17)0.0366 (16)0.0323 (16)0.0091 (13)0.0071 (13)0.0164 (13)
C110.0414 (18)0.0320 (15)0.0290 (15)0.0101 (13)0.0057 (13)0.0099 (13)
C120.0385 (18)0.0393 (17)0.0312 (16)0.0139 (14)0.0084 (13)0.0156 (14)
C130.0305 (16)0.0301 (15)0.0334 (16)0.0066 (12)0.0041 (12)0.0038 (13)
C140.0339 (18)0.0309 (16)0.0451 (19)0.0074 (13)0.0027 (14)0.0066 (14)
C150.049 (2)0.0377 (19)0.069 (3)0.0014 (16)0.0086 (18)0.0158 (18)
C160.074 (3)0.0260 (15)0.0331 (17)0.0057 (15)0.0109 (16)0.0148 (13)
C170.085 (3)0.0392 (19)0.050 (2)0.0057 (19)0.026 (2)0.0244 (17)
C180.096 (3)0.0300 (17)0.049 (2)0.0127 (18)0.004 (2)0.0191 (16)
C190.097 (3)0.0339 (18)0.043 (2)−0.0061 (19)0.003 (2)0.0219 (16)
C200.046 (2)0.0450 (18)0.0281 (16)0.0178 (15)0.0068 (14)0.0154 (14)
C210.107 (4)0.065 (3)0.0338 (19)0.051 (2)0.019 (2)0.0190 (18)
C220.056 (2)0.078 (3)0.0365 (19)0.001 (2)0.0018 (16)0.0340 (19)
C230.048 (2)0.0476 (19)0.0347 (17)0.0154 (16)0.0007 (15)0.0153 (15)
C240.043 (3)0.038 (2)0.034 (2)0.014 (2)0.0033 (19)0.0117 (19)
C250.043 (3)0.049 (3)0.046 (2)0.005 (2)0.003 (2)0.005 (2)
C260.058 (3)0.063 (3)0.040 (2)0.013 (2)0.001 (2)−0.003 (2)
C270.073 (4)0.060 (3)0.037 (2)0.025 (3)0.008 (2)0.011 (2)
C280.070 (4)0.050 (3)0.047 (3)0.021 (3)0.017 (3)0.022 (2)
C290.069 (4)0.036 (2)0.033 (2)0.017 (2)0.008 (2)0.0136 (19)
C24A0.044 (7)0.036 (6)0.023 (6)0.006 (6)0.001 (6)0.018 (5)
C25A0.048 (7)0.055 (7)0.031 (6)0.007 (6)0.002 (5)0.020 (5)
C26A0.050 (7)0.053 (7)0.038 (6)0.002 (6)0.000 (6)0.014 (5)
C27A0.049 (7)0.042 (7)0.034 (7)0.005 (6)0.002 (6)0.010 (6)
C28A0.045 (7)0.035 (6)0.033 (6)0.017 (5)0.007 (6)0.014 (5)
C29A0.041 (7)0.028 (6)0.033 (6)0.008 (6)0.002 (6)0.017 (5)
C300.074 (3)0.043 (2)0.043 (2)−0.0019 (19)0.0022 (19)0.0182 (17)
C310.081 (3)0.057 (2)0.051 (2)−0.007 (2)−0.009 (2)0.034 (2)
C320.111 (4)0.041 (2)0.054 (2)−0.005 (2)−0.024 (3)0.0244 (19)
C330.116 (5)0.056 (3)0.060 (3)0.016 (3)−0.001 (3)0.017 (2)
C340.103 (4)0.062 (3)0.085 (3)0.024 (3)0.029 (3)0.024 (3)
C350.091 (4)0.055 (3)0.077 (3)0.010 (2)0.032 (3)0.017 (2)
C360.043 (2)0.055 (2)0.042 (2)−0.0004 (17)0.0077 (16)−0.0020 (17)
C370.041 (2)0.077 (3)0.054 (2)0.003 (2)0.0028 (18)−0.009 (2)
C380.057 (2)0.057 (2)0.038 (2)−0.0003 (19)0.0006 (17)0.0023 (17)
C390.064 (2)0.048 (2)0.0321 (18)0.0109 (18)0.0094 (16)0.0104 (15)
C400.054 (2)0.0462 (19)0.0423 (19)0.0122 (17)0.0094 (16)0.0168 (16)
C410.046 (2)0.0422 (18)0.0353 (17)0.0000 (15)0.0030 (14)0.0121 (15)
O50.056 (2)0.053 (2)0.078 (4)0.009 (2)0.005 (2)0.034 (2)
C420.074 (4)0.050 (3)0.055 (3)−0.005 (3)−0.014 (3)0.035 (3)
C430.113 (5)0.061 (3)0.061 (3)−0.020 (3)−0.009 (3)0.035 (3)
C440.178 (6)0.082 (4)0.055 (3)−0.026 (4)0.010 (4)0.036 (3)
C450.204 (6)0.080 (4)0.047 (3)−0.029 (4)0.015 (4)0.025 (3)
C460.177 (6)0.065 (4)0.053 (3)−0.027 (4)0.003 (4)0.026 (3)
C470.107 (4)0.056 (3)0.056 (3)−0.013 (3)−0.004 (3)0.029 (3)
O5A0.058 (6)0.052 (6)0.027 (5)0.000 (5)0.003 (4)0.021 (4)
C42A0.046 (6)0.062 (6)0.020 (5)0.012 (5)0.003 (4)0.020 (5)
C43A0.037 (6)0.072 (7)0.028 (5)0.004 (5)0.001 (4)0.029 (5)
C44A0.041 (6)0.088 (8)0.043 (6)0.002 (6)0.006 (5)0.026 (5)
C45A0.050 (7)0.101 (9)0.045 (7)0.000 (7)0.015 (6)0.013 (6)
C46A0.054 (7)0.091 (8)0.048 (7)0.007 (6)0.004 (6)0.005 (6)
C47A0.047 (7)0.073 (8)0.037 (6)0.015 (6)0.012 (6)0.001 (6)
C480.068 (4)0.067 (3)0.183 (7)0.011 (3)0.005 (4)0.054 (4)
C490.112 (5)0.085 (4)0.164 (7)0.006 (4)0.012 (5)0.050 (5)
C500.126 (6)0.072 (4)0.157 (7)−0.009 (4)0.018 (5)0.055 (4)
C510.052 (2)0.054 (2)0.062 (2)0.0115 (17)0.0103 (18)0.0383 (19)
C520.047 (2)0.054 (2)0.060 (2)0.0032 (17)0.0028 (17)0.0355 (19)
C530.061 (2)0.045 (2)0.052 (2)0.0049 (17)0.0048 (18)0.0283 (17)
C540.071 (3)0.150 (5)0.115 (4)0.032 (3)0.027 (3)0.108 (4)

Geometric parameters (Å, °)

S1—N11.659 (3)C22—H22C0.9800
S1—C31.711 (3)C23—H23A0.9800
S2—N141.654 (3)C23—H23B0.9800
S2—C131.725 (3)C23—H23C0.9800
Na1—O82.336 (3)C24—C251.3900
Na1—N72.420 (3)C24—C291.3900
Na1—O22.437 (2)C25—C261.3900
Na1—N112.642 (3)C25—H250.9500
Na1—N52.644 (3)C26—C271.3900
O1—C81.253 (3)C26—H260.9500
O2—C241.357 (3)C27—C281.3900
O2—C24A1.528 (10)C27—H270.9500
O2—H2O0.8400C28—C291.3900
O3—C301.388 (4)C28—H280.9500
O3—H3O0.8400C29—H290.9500
O4—C361.367 (4)C24A—C25A1.3900
O4—H4O0.8400C24A—C29A1.3900
O6—C481.330 (9)C25A—C26A1.3900
O6—H6O0.8400C25A—H25A0.9500
O7—C511.301 (5)C26A—C27A1.3900
O7—H7O0.8400C26A—H26A0.9500
O8—C541.452 (5)C27A—C28A1.3900
O8—H8O0.8400C27A—H27A0.9500
N1—C21.323 (4)C28A—C29A1.3900
N2—C31.310 (4)C28A—H28A0.9500
N2—C21.360 (4)C29A—H29A0.9500
N3—N41.295 (4)C30—C311.378 (5)
N3—C31.389 (4)C30—C351.382 (6)
N4—C41.351 (4)C31—C321.410 (6)
N5—C61.314 (4)C31—H310.9500
N5—N61.413 (3)C32—C331.374 (7)
N6—C51.374 (4)C32—H320.9500
N6—C71.394 (4)C33—C341.367 (7)
N7—C91.335 (4)C33—H330.9500
N7—C71.339 (4)C34—C351.403 (6)
N8—C91.323 (4)C34—H340.9500
N8—C81.363 (4)C35—H350.9500
N9—C71.317 (4)C36—C411.361 (5)
N9—C81.372 (4)C36—C371.388 (5)
N10—C101.368 (4)C37—C381.374 (5)
N10—C91.401 (4)C37—H370.9500
N10—N111.418 (3)C38—C391.369 (5)
N11—C121.314 (4)C38—H380.9500
N12—N131.308 (3)C39—C401.387 (5)
N12—C111.347 (4)C39—H390.9500
N13—C131.378 (4)C40—C411.379 (4)
N14—C141.309 (4)C40—H400.9500
N15—C131.318 (4)C41—H410.9500
N15—C141.372 (4)O5—C421.358 (5)
N16—C51.322 (4)O5—H5O0.8400
N16—H16N0.8800C42—C431.3900
N16—H16M0.8800C42—C471.3900
N17—C101.325 (4)C43—C441.3900
N17—H17N0.8800C43—H430.9500
N17—H17M0.8800C44—C451.3900
C1—C21.500 (5)C44—H440.9500
C1—H1A0.9800C45—C461.3900
C1—H1B0.9800C45—H450.9500
C1—H1C0.9800C46—C471.3900
C4—C51.418 (4)C46—H460.9500
C4—C61.438 (4)C47—H470.9500
C6—C161.510 (4)O5A—C42A1.365 (12)
C10—C111.408 (4)O5A—H5OA0.8400
C11—C121.444 (4)C42A—C43A1.3900
C12—C201.513 (4)C42A—C47A1.3900
C14—C151.486 (5)C43A—C44A1.3900
C15—H15A0.9800C43A—H43A0.9500
C15—H15B0.9800C44A—C45A1.3900
C15—H15C0.9800C44A—H44A0.9500
C16—C191.520 (5)C45A—C46A1.3900
C16—C171.537 (5)C45A—H45A0.9500
C16—C181.538 (4)C46A—C47A1.3900
C17—H17A0.9800C46A—H46A0.9500
C17—H17B0.9800C47A—H47A0.9500
C17—H17C0.9800C48—C501.353 (9)
C18—H18A0.9800C48—C491.374 (9)
C18—H18B0.9800C49—C50i1.405 (8)
C18—H18C0.9800C49—H490.9500
C19—H19A0.9800C50—C49i1.405 (8)
C19—H19B0.9800C50—H500.9500
C19—H19C0.9800C51—C521.380 (5)
C20—C231.521 (4)C51—C53ii1.394 (5)
C20—C221.528 (5)C52—C531.382 (5)
C20—C211.531 (4)C52—H520.9500
C21—H21A0.9800C53—C51ii1.394 (5)
C21—H21B0.9800C53—H530.9500
C21—H21C0.9800C54—H54A0.9800
C22—H22A0.9800C54—H54B0.9800
C22—H22B0.9800C54—H54C0.9800
N1—S1—C390.98 (15)H22A—C22—H22B109.5
N14—S2—C1390.84 (15)C20—C22—H22C109.5
O8—Na1—N7118.62 (9)H22A—C22—H22C109.5
O8—Na1—O2121.65 (9)H22B—C22—H22C109.5
N7—Na1—O2119.57 (9)C20—C23—H23A109.5
O8—Na1—N1197.59 (9)C20—C23—H23B109.5
N7—Na1—N1165.51 (8)H23A—C23—H23B109.5
O2—Na1—N11109.37 (9)C20—C23—H23C109.5
O8—Na1—N5104.19 (9)H23A—C23—H23C109.5
N7—Na1—N565.04 (8)H23B—C23—H23C109.5
O2—Na1—N596.00 (9)O2—C24—C25120.7 (3)
N11—Na1—N5130.53 (8)O2—C24—C29119.3 (3)
C24—O2—C24A15.1 (6)C25—C24—C29120.0
C24—O2—Na1140.8 (2)C24—C25—C26120.0
C24A—O2—Na1136.1 (5)C24—C25—H25120.0
C24—O2—H2O109.5C26—C25—H25120.0
C24A—O2—H2O102.3C27—C26—C25120.0
Na1—O2—H2O103.0C27—C26—H26120.0
C30—O3—H3O109.5C25—C26—H26120.0
C36—O4—H4O109.5C26—C27—C28120.0
C48—O6—H6O109.5C26—C27—H27120.0
C51—O7—H7O109.5C28—C27—H27120.0
C54—O8—Na1125.3 (2)C29—C28—C27120.0
C54—O8—H8O109.5C29—C28—H28120.0
Na1—O8—H8O113.0C27—C28—H28120.0
C2—N1—S1109.0 (2)C28—C29—C24120.0
C3—N2—C2108.6 (3)C28—C29—H29120.0
N4—N3—C3112.2 (3)C24—C29—H29120.0
N3—N4—C4114.1 (3)C25A—C24A—C29A120.0
C6—N5—N6105.8 (2)C25A—C24A—O2115.8 (8)
C6—N5—Na1142.0 (2)C29A—C24A—O2123.6 (7)
N6—N5—Na1112.22 (17)C24A—C25A—C26A120.0
C5—N6—C7127.7 (2)C24A—C25A—H25A120.0
C5—N6—N5111.5 (2)C26A—C25A—H25A120.0
C7—N6—N5120.7 (2)C27A—C26A—C25A120.0
C9—N7—C7111.0 (2)C27A—C26A—H26A120.0
C9—N7—Na1124.4 (2)C25A—C26A—H26A120.0
C7—N7—Na1124.62 (19)C28A—C27A—C26A120.0
C9—N8—C8115.5 (3)C28A—C27A—H27A120.0
C7—N9—C8115.9 (3)C26A—C27A—H27A120.0
C10—N10—C9127.2 (2)C27A—C28A—C29A120.0
C10—N10—N11111.7 (2)C27A—C28A—H28A120.0
C9—N10—N11120.9 (2)C29A—C28A—H28A120.0
C12—N11—N10105.4 (2)C28A—C29A—C24A120.0
C12—N11—Na1142.8 (2)C28A—C29A—H29A120.0
N10—N11—Na1111.76 (17)C24A—C29A—H29A120.0
N13—N12—C11114.4 (3)C31—C30—C35120.1 (4)
N12—N13—C13111.0 (2)C31—C30—O3117.6 (4)
C14—N14—S2110.1 (2)C35—C30—O3122.3 (4)
C13—N15—C14108.6 (3)C30—C31—C32118.8 (5)
C5—N16—H16N120.0C30—C31—H31120.6
C5—N16—H16M120.0C32—C31—H31120.6
H16N—N16—H16M120.0C33—C32—C31121.3 (4)
C10—N17—H17N120.0C33—C32—H32119.3
C10—N17—H17M120.0C31—C32—H32119.3
H17N—N17—H17M120.0C34—C33—C32119.2 (5)
C2—C1—H1A109.5C34—C33—H33120.4
C2—C1—H1B109.5C32—C33—H33120.4
H1A—C1—H1B109.5C33—C34—C35120.5 (5)
C2—C1—H1C109.5C33—C34—H34119.8
H1A—C1—H1C109.5C35—C34—H34119.8
H1B—C1—H1C109.5C30—C35—C34120.0 (5)
N1—C2—N2118.1 (3)C30—C35—H35120.0
N1—C2—C1120.9 (3)C34—C35—H35120.0
N2—C2—C1120.9 (3)C41—C36—O4122.4 (3)
N2—C3—N3120.1 (3)C41—C36—C37120.2 (3)
N2—C3—S1113.2 (2)O4—C36—C37117.4 (3)
N3—C3—S1126.7 (3)C38—C37—C36119.9 (4)
N4—C4—C5127.1 (3)C38—C37—H37120.1
N4—C4—C6127.4 (3)C36—C37—H37120.1
C5—C4—C6105.5 (3)C39—C38—C37120.5 (4)
N16—C5—N6125.1 (3)C39—C38—H38119.8
N16—C5—C4129.2 (3)C37—C38—H38119.8
N6—C5—C4105.7 (2)C38—C39—C40119.0 (3)
N5—C6—C4111.5 (3)C38—C39—H39120.5
N5—C6—C16121.9 (3)C40—C39—H39120.5
C4—C6—C16126.5 (3)C41—C40—C39120.8 (3)
N9—C7—N7128.1 (3)C41—C40—H40119.6
N9—C7—N6114.7 (3)C39—C40—H40119.6
N7—C7—N6117.2 (2)C36—C41—C40119.5 (3)
O1—C8—N8119.3 (3)C36—C41—H41120.2
O1—C8—N9119.8 (3)C40—C41—H41120.2
N8—C8—N9120.9 (3)C42—O5—H5O109.5
N8—C9—N7128.5 (3)O5—C42—C43117.6 (3)
N8—C9—N10114.1 (3)O5—C42—C47122.4 (3)
N7—C9—N10117.4 (3)C43—C42—C47120.0
N17—C10—N10126.4 (3)C42—C43—C44120.0
N17—C10—C11127.6 (3)C42—C43—H43120.0
N10—C10—C11105.9 (3)C44—C43—H43120.0
N12—C11—C10127.9 (3)C43—C44—C45120.0
N12—C11—C12126.4 (3)C43—C44—H44120.0
C10—C11—C12105.7 (3)C45—C44—H44120.0
N11—C12—C11111.3 (3)C46—C45—C44120.0
N11—C12—C20121.8 (3)C46—C45—H45120.0
C11—C12—C20126.9 (3)C44—C45—H45120.0
N15—C13—N13122.4 (3)C45—C46—C47120.0
N15—C13—S2112.6 (2)C45—C46—H46120.0
N13—C13—S2125.0 (2)C47—C46—H46120.0
N14—C14—N15117.9 (3)C46—C47—C42120.0
N14—C14—C15122.0 (3)C46—C47—H47120.0
N15—C14—C15120.1 (3)C42—C47—H47120.0
C14—C15—H15A109.5C42A—O5A—H5OA109.5
C14—C15—H15B109.5O5A—C42A—C43A115.2 (8)
H15A—C15—H15B109.5O5A—C42A—C47A124.7 (8)
C14—C15—H15C109.5C43A—C42A—C47A120.0
H15A—C15—H15C109.5C42A—C43A—C44A120.0
H15B—C15—H15C109.5C42A—C43A—H43A120.0
C6—C16—C19110.0 (3)C44A—C43A—H43A120.0
C6—C16—C17109.3 (3)C43A—C44A—C45A120.0
C19—C16—C17110.3 (3)C43A—C44A—H44A120.0
C6—C16—C18109.1 (3)C45A—C44A—H44A120.0
C19—C16—C18108.6 (3)C44A—C45A—C46A120.0
C17—C16—C18109.7 (3)C44A—C45A—H45A120.0
C16—C17—H17A109.5C46A—C45A—H45A120.0
C16—C17—H17B109.5C47A—C46A—C45A120.0
H17A—C17—H17B109.5C47A—C46A—H46A120.0
C16—C17—H17C109.5C45A—C46A—H46A120.0
H17A—C17—H17C109.5C46A—C47A—C42A120.0
H17B—C17—H17C109.5C46A—C47A—H47A120.0
C16—C18—H18A109.5C42A—C47A—H47A120.0
C16—C18—H18B109.5O6—C48—C50130.8 (7)
H18A—C18—H18B109.5O6—C48—C49109.8 (8)
C16—C18—H18C109.5C50—C48—C49119.1 (6)
H18A—C18—H18C109.5C48—C49—C50i117.7 (7)
H18B—C18—H18C109.5C48—C49—H49121.1
C16—C19—H19A109.5C50i—C49—H49121.1
C16—C19—H19B109.5C48—C50—C49i123.2 (7)
H19A—C19—H19B109.5C48—C50—H50118.4
C16—C19—H19C109.5C49i—C50—H50118.4
H19A—C19—H19C109.5O7—C51—C52122.9 (4)
H19B—C19—H19C109.5O7—C51—C53ii116.9 (4)
C12—C20—C23109.1 (2)C52—C51—C53ii119.9 (3)
C12—C20—C22110.1 (3)C51—C52—C53120.6 (4)
C23—C20—C22108.0 (3)C51—C52—H52119.7
C12—C20—C21109.8 (3)C53—C52—H52119.7
C23—C20—C21108.8 (3)C52—C53—C51ii119.5 (4)
C22—C20—C21111.0 (3)C52—C53—H53120.3
C20—C21—H21A109.5C51ii—C53—H53120.3
C20—C21—H21B109.5O8—C54—H54A109.5
H21A—C21—H21B109.5O8—C54—H54B109.5
C20—C21—H21C109.5H54A—C54—H54B109.5
H21A—C21—H21C109.5O8—C54—H54C109.5
H21B—C21—H21C109.5H54A—C54—H54C109.5
C20—C22—H22A109.5H54B—C54—H54C109.5
C20—C22—H22B109.5

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2O···O1iii0.841.842.682 (2)175
O3—H3O···N10.842.012.835 (3)166
O4—H4O···N140.841.992.757 (3)152
O5—H5O···N20.842.102.926 (6)170
O5A—H5OA···N20.842.022.831 (14)162
O7—H7O···N150.842.212.975 (5)152
O8—H8O···O1iv0.841.992.822 (3)173
N16—H16M···N30.882.162.719 (4)121
N16—H16N···N90.882.052.660 (3)126
N17—H17M···N130.882.132.705 (2)122
N17—H17N···N80.882.062.661 (3)125

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2750).

References

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