Nicotinium picrate

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organic papers

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Anithaet al. _C

6H6NO2+C6H2N3O7 doi:10.1107/S160053680502221X Acta Cryst.(2005). E61, o2556–o2558

Acta Crystallographica Section E

Structure Reports

Online

ISSN 1600-5368

Nicotinium picrate

K. Anitha, S. Athimoolam and R. K. Rajaram*

Department of Physics, Madurai Kamaraj University, Madurai 625 021, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 293 K

Mean(C–C) = 0.004 A˚ Rfactor = 0.045 wRfactor = 0.136

Data-to-parameter ratio = 11.0

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

The title compound, C6H6NO2 +

C6H2N3O7

, is the picrate salt of the nicotinium cation. In the picrate anion, theorthonitro groups are twisted out of the plane of the ring, whereas the

para nitro group lies approximately in the ring plane. Hydrogen bonds from the nicotinate cation link two different picrate anions, forming a straight chain along thebaxis. The picrate anions are stacked in columns along [010].

Comment

Nicotinic acid (3-pyridine carboxylic acid) is a B vitamin known as niacin. The crystal structures of nicotinic acid (Wright & King, 1953; Kutoglu & Scheringer, 1983), nicotin-amide (Wright & King, 1954), isonicotinic acid hydrazide (Bhatet al., 1974), 1-methyl nicotinamide iodide, chloride and picrate (Freeman & Bugg, 1974), isonicotinic acid (Takusa-gawa & Shimada, 1976), nicotinoylglycine (Krishnaswamy et al., 1987), 6-aminonicotinic acid hydrochloride (Giantsidis & Turnbull, 2000), and dinicotinamidium squarate (Bulutet al., 2003) have been reported. The structure of the title compound, (I), is reported here.

In (I) (Fig. 1), the H atom of the hydroxy group of picric acid has been transferred to the N atom of nicotinic acid, leading to the formation of a molecular complex. The bond lengths and bond angles in the pyridine ring of the nicotinium cation are comparable to the average values of 1.38 A˚ for the C—C bonds and 1.33 A˚ for the C—N bonds found in dinico-tinamidium squarate (Bulutet al., 2003) and nicotinoylglycine (Krishnaswamy et al., 1987). The C11—C12 bond length is similar to that observed in dinicotinamidium squarate (Bulut

et al., 2003), while atom O1B is identified as the hydroxy O atom by comparison of the C11—O1A and C11—O1B

distances. A comparison of equivalent bond distances invol-ving the pyridine ring atoms of (I) with the values found in nicotinic acid (Wright & King, 1953) shows that the positive charge is localized on the pyridine N atom and does not have much effect on the ring structure. These distances also

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compare well with those for 6-aminonicotinic acid hydro-chloride (Giantsidis & Turnbull, 2000) and dinicotinamidium squarate (Bulutet al., 2003). The nicotinium cation is planar, and the planes of the nicotinium cation and the ring of the picrate anion are inclined to one another at 62.9 (1)_{. In the}

picrate anion, removal of the phenol H atom leads to a shortening of the C1—O1 bond, while the C1—C2 and C1— C6 distances increase as observed previously (Anitha et al., 2004; Muthamizhchelvan et al., 2005). The torsion angles involving theortho-related nitro groups in the picrate anion (C1—C6—N3—O6,O7 and C1—C2—N1—O2,O3) are 144.0 (3), 139.6 (3), 131.5 (3) and 132.1 (3)_{, respectively}

(Table 1). It has been found that in most picrates theortho -related nitro groups, which are commonly involved in hydrogen-bonding interactions, are more likely to be rotated out of the molecular plane than the para nitro substituent (Anithaet al., 2004; Kaiet al., 1994; Smithet al., 2004; Gartland

et al., 1974). Here, even though one of theorthonitro groups is not involved in hydrogen bonding, it is still twisted from the plane of the ring, while theparanitro group lies approximately in the ring plane. It is also found that the twisting of these nitro groups is independent of C—N bond distances (Soriano-Garciaet al., 1978; Srikrishnanet al., 1980). The nitro O atoms not involved in hydrogen bonding have largeUeqvalues. In the

crystal structure, the cations and anions are linked by strong N11—H111 O1 and O1B—H11B O1 hydrogen bonds (Table 2). The structure is also stabilized by C—H O hydrogen bonding. These hydrogen bonds link the layers of cations with the layers of anions, with each nicotinium cation linking two different picrate anions to form a straight chain along the b axis (Fig. 2). The picrate anions are stacked in columns along [010].

Experimental

The title compound was crystallized from a nicotonic acid and picric acid mixture in the stoichiometric ratio of 1:1 at room temperature by slow evaporation.

Crystal data

C6H6NO2+C6H2N3O7

Mr= 352.22

Triclinic,P1

a= 8.063 (3) A˚

b= 8.080 (3) A˚

c= 12.030 (5) A˚

= 93.27 (3)

= 95.87 (4)

= 113.46 (3) V= 711.1 (5) A˚3

Z= 2

Dx= 1.645 Mg m

3

Dm= 1.639 Mg m

3

Dmmeasured by flotation in CHBr3

and CCl4

MoKradiation Cell parameters from 25

reflections

= 10.2–14.3

= 0.14 mm1

T= 293 (2) K Block, yellow 0.190.170.15 mm

Data collection

Nonius MACH3 four-circle diffractometer

!–2scans

Absorption correction: scan (Northet al., 1968)

Tmin= 0.973,Tmax= 0.978

3091 measured reflections 2509 independent reflections 1765 reflections withI> 2(I)

Rint= 0.012 max= 25

h=1!9

k=9!9

l=14!14 3 standard reflections

frequency: 60 min intensity decay: none

Refinement

Refinement onF2 R[F2_{> 2}₍_F2_{)] = 0.045}

wR(F2_{) = 0.136}

S= 1.02 2509 reflections 228 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0601P)2

+ 0.5668P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.50 e A˚

3 min=0.26 e A˚

3

Extinction correction:SHELXTL/

PC

Extinction coefficient: 0.029 (5)

Table 1

Selected geometric parameters (A˚ ,_).

O1A—C11 1.196 (3)

O1B—C11 1.308 (3)

N11—C15 1.332 (4)

N11—C16 1.332 (3)

O1—C1 1.279 (3)

C1—C6 1.423 (3)

C1—C2 1.431 (3)

C15—N11—C16 122.7 (2)

O1A—C11—O1B 125.6 (3)

O1A—C11—C12 122.2 (2)

O1B—C11—C12 112.3 (2)

N11—C15—C14 119.8 (3)

N11—C16—C12 119.7 (2)

O1—C1—C6 123.0 (2)

O1—C1—C2 124.4 (2)

C6—C1—C2 112.5 (2)

O2—N1—C2—C3 144.0 (3)

O3—N1—C2—C1 139.6 (3)

O4—N2—C4—C5 170.2 (3)

O5—N2—C4—C3 171.0 (3)

O7—N3—C6—C5 131.5 (3)

[image:2.610.313.565.599.648.2]

O6—N3—C6—C1 132.1 (3)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N11—H11 O1 0.86 1.85 2.711 (3) 174

O1B—H11B O1i

0.82 1.75 2.563 (3) 170

C16—H16 O7 0.93 2.55 2.962 (4) 107

Symmetry code: (i)x;y1;z.

All H atoms were placed in geometrically calculated positions, with C—H distances of 0.93 A˚ , an N—H distance of 0.86 A˚ and an O—H distance of 0.82 A˚ , and allowed to ride on the carrier atom with

Uiso(H) equal to 1.2Ueq(C,N) and 1.5Ueq(O).

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement:CAD-4 EXPRESS; data reduction:XCAD4(Harms & Wocadlo, 1995); program(s) used to solve structure:SHELXTL/PC

organic papers

Acta Cryst.(2005). E61, o2556–o2558 Anithaet al. _C

6H6NO2+C6H2N3O7

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Figure 1

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(Bruker, 2000); program(s) used to refine structure:SHELXTL/PC; molecular graphics:SHELXTL/PC; software used to prepare mate-rial for publication:SHELXTL/PC.

The authors thank the Department of Science and Tech-nology, Government of India, for establishing a single-crystal

diffractometer facility at the School of Physics, Madurai Kamaraj University, Madurai, through the FIST programme.

References

Anitha, K., Sridhar, B. & Rajaram, R. K. (2004).Acta Cryst.E60, o1530– o1532.

Bhat, T. N., Singh, T. P. & Vijayan, M. (1974).Acta Cryst.B30, 2921–2922. Bruker (2000). SHELXTL/PC. Version 6.10. Bruker AXS Inc., Madison,

Wisconsin, USA.

Bulut, A., Yesilel, O. Z., Dege, N., Icbudak, H., Olmaz, H. & Bujukgungor, O. (2003).Acta Cryst.C59, o727–o729.

Enraf–Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf–Nonius, Delft, The Netherlands.

Freeman, G. R. & Bugg, C. E. (1974).Acta Cryst.B30, 431–443.

Gartland, G. L., Freeman, G. R. & Bugg, C. E. (1974).Acta Cryst.B30, 1841– 1849.

Giantsidis, J. & Turnbull, M. M. (2000).Acta Cryst.C56, 334–335.

Harms, K. & Wocadlo, S. (1995).XCAD4.University of Marburg, Germany. Kai, T., Goto, M., Furuhata, K. & Takayanagi, H. (1994).Anal. Sci.10, 359–

360.

Krishnaswamy, S., Pattabhi, V. & Guru Row, T. N. (1987).Acta Cryst.C43, 728– 729.

Kutoglu, A. & Scheringer, C. (1983).Acta Cryst.C39, 232–234.

Muthamizhchelvan, C., Saminathan, K., Fraanje, J., Pescher, R. & Sivakumar, K. (2005).Acta Cryst.E61, o1153–o1155.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351– 359.

Smith, G., Wermuth, U. D. & Healy, P. C. (2004).Acta Cryst.E60, o1800–o1803. Soriano-Garcia, M., Srikrishnan, T. & Parthasarathy, R. (1978).Acta Cryst.

A34, s114.

Srikrishnan, T., Soriano-Garcia, M. & Parthasarathy, R. (1980).Z. Kristallogr.

151, 317–323.

Takusagawa, F. & Shimada, A. (1976).Acta Cryst.B32, 1925–1927. Wright, W. B. & King, G. S. D. (1953).Acta Cryst.6, 305–310. Wright, W. B. & King, G. S. D. (1954).Acta Cryst.7, 283–288.

organic papers

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[image:3.610.46.294.73.289.2]

6H6NO2+C6H2N3O7 Acta Cryst.(2005). E61, o2556–o2558

Figure 2

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supporting information

sup-1 Acta Cryst. (2005). E61, o2556–o2558

supporting information

Acta Cryst. (2005). E61, o2556–o2558 [https://doi.org/10.1107/S160053680502221X]

Nicotinium picrate

K. Anitha, S. Athimoolam and R. K. Rajaram

Nicotinium picrate

Crystal data

C6H6NO2+·C6H2N3O7−

Mr = 352.22 Triclinic, P1 Hall symbol: -P 1 a = 8.063 (3) Å b = 8.080 (3) Å c = 12.030 (5) Å α = 93.27 (3)° β = 95.87 (4)° γ = 113.46 (3)° V = 711.1 (5) Å3

Z = 2

F(000) = 360 Dx = 1.645 Mg m−3

Dm = 1.639 Mg m−3

Dm measured by flotation; CHBr3 & CCl4

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 10.2–14.3°

µ = 0.15 mm−1

T = 293 K Needle, yellow 0.19 × 0.17 × 0.15 mm

Data collection

Nonius MACH3 sealed-tube diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω–2θ scans

Absorption correction: ψ scan (North et al., 1968)

Tmin = 0.973, Tmax = 0.978

3091 measured reflections

2509 independent reflections 1765 reflections with I > 2σ(I) Rint = 0.012

θmax = 25°, θmin = 2.8°

h = −1→9 k = −9→9 l = −14→14

3 standard reflections every 60 min intensity decay: none

Refinement

Refinement on F2

Least-squares matrix: full R[F2_{> 2σ(F}2_{)] = 0.045}

wR(F2_{) = 0.136}

S = 1.02 2509 reflections 228 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0601P)2 + 0.5668P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.50 e Å−3

Δρmin = −0.26 e Å−3

Extinction correction: SHELXTL/PC, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

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supporting information

Special details

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2_{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

O1A 0.6967 (4) −0.3057 (3) 0.94419 (19) 0.0712 (7)

O1B 0.5023 (3) −0.3033 (3) 0.79944 (17) 0.0587 (6)

H11B 0.4910 −0.4076 0.7837 0.088*

N11 0.6202 (3) 0.2269 (3) 0.87177 (18) 0.0421 (6)

H11 0.5668 0.2776 0.8287 0.051*

C11 0.6248 (4) −0.2291 (4) 0.8880 (2) 0.0396 (6)

C12 0.6672 (3) −0.0319 (3) 0.91400 (19) 0.0339 (6)

C13 0.7897 (4) 0.0683 (4) 1.0069 (2) 0.0391 (6)

H13 0.8490 0.0142 1.0529 0.047*

C14 0.8236 (4) 0.2488 (4) 1.0312 (2) 0.0448 (7)

H14 0.9041 0.3169 1.0941 0.054*

C15 0.7367 (4) 0.3266 (4) 0.9609 (2) 0.0463 (7)

H15 0.7592 0.4485 0.9755 0.056*

C16 0.5828 (4) 0.0519 (4) 0.8465 (2) 0.0384 (6)

H16 0.5002 −0.0133 0.7837 0.046*

O1 0.4312 (3) 0.3651 (2) 0.73443 (15) 0.0466 (5)

O2 0.1092 (5) 0.3296 (5) 0.8122 (2) 0.1135 (13)

O3 −0.0094 (4) 0.4605 (4) 0.7055 (2) 0.0866 (9)

O4 −0.1795 (3) 0.1255 (4) 0.3199 (2) 0.0717 (7)

O5 0.0448 (4) 0.1230 (5) 0.24188 (19) 0.0938 (10)

O6 0.6432 (3) 0.3136 (4) 0.4727 (2) 0.0802 (8)

O7 0.5993 (3) 0.1686 (4) 0.61744 (19) 0.0703 (7)

N1 0.0753 (4) 0.3677 (4) 0.7216 (2) 0.0549 (7)

N2 −0.0215 (3) 0.1476 (4) 0.3238 (2) 0.0517 (6)

N3 0.5514 (3) 0.2449 (3) 0.54566 (19) 0.0414 (5)

C1 0.3226 (3) 0.3086 (3) 0.64204 (19) 0.0326 (6)

C2 0.1439 (3) 0.3077 (4) 0.6254 (2) 0.0367 (6)

C3 0.0333 (3) 0.2593 (4) 0.5240 (2) 0.0392 (6)

H3 −0.0812 0.2626 0.5177 0.047*

C4 0.0953 (3) 0.2055 (4) 0.4315 (2) 0.0374 (6)

C5 0.2661 (4) 0.2040 (3) 0.4391 (2) 0.0368 (6)

H5 0.3085 0.1718 0.3758 0.044*

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supporting information

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1A 0.108 (2) 0.0492 (12) 0.0591 (13) 0.0441 (13) −0.0265 (13) −0.0010 (10)

O1B 0.0718 (15) 0.0482 (12) 0.0531 (12) 0.0315 (11) −0.0225 (11) −0.0160 (10)

N11 0.0485 (13) 0.0431 (13) 0.0404 (12) 0.0251 (11) −0.0002 (10) 0.0105 (10)

C11 0.0505 (16) 0.0425 (14) 0.0302 (13) 0.0248 (13) 0.0008 (12) 0.0018 (11)

C12 0.0384 (14) 0.0403 (14) 0.0265 (12) 0.0202 (12) 0.0017 (10) 0.0031 (10)

C13 0.0450 (15) 0.0445 (15) 0.0313 (13) 0.0239 (13) −0.0036 (11) 0.0024 (11)

C14 0.0501 (17) 0.0427 (15) 0.0380 (14) 0.0188 (13) −0.0058 (12) −0.0030 (12)

C15 0.0547 (17) 0.0362 (14) 0.0486 (16) 0.0189 (13) 0.0080 (14) 0.0045 (12)

C16 0.0398 (15) 0.0445 (15) 0.0319 (13) 0.0198 (12) −0.0019 (11) 0.0030 (11)

O1 0.0588 (12) 0.0456 (11) 0.0363 (10) 0.0302 (10) −0.0189 (9) −0.0114 (8)

O2 0.165 (3) 0.178 (4) 0.0506 (16) 0.118 (3) 0.0379 (18) 0.0215 (19)

O3 0.0907 (19) 0.103 (2) 0.0904 (19) 0.0675 (18) 0.0152 (15) −0.0139 (16)

O4 0.0431 (13) 0.0940 (18) 0.0681 (15) 0.0256 (12) −0.0209 (11) −0.0015 (13)

O5 0.0771 (18) 0.173 (3) 0.0332 (12) 0.061 (2) −0.0124 (12) −0.0163 (15)

O6 0.0556 (14) 0.126 (2) 0.0836 (17) 0.0523 (15) 0.0308 (13) 0.0499 (17)

O7 0.0622 (14) 0.111 (2) 0.0645 (14) 0.0587 (15) 0.0103 (11) 0.0338 (14)

N1 0.0548 (16) 0.0732 (18) 0.0442 (15) 0.0350 (14) 0.0071 (12) −0.0026 (13)

N2 0.0462 (15) 0.0632 (16) 0.0403 (14) 0.0214 (13) −0.0122 (11) 0.0002 (12)

N3 0.0353 (12) 0.0534 (14) 0.0399 (12) 0.0231 (11) 0.0014 (10) 0.0065 (11)

C1 0.0379 (13) 0.0299 (12) 0.0296 (12) 0.0161 (11) −0.0041 (10) −0.0012 (10)

C2 0.0384 (14) 0.0425 (14) 0.0339 (13) 0.0214 (12) 0.0062 (11) 0.0022 (11)

C3 0.0292 (13) 0.0448 (15) 0.0453 (15) 0.0182 (12) −0.0009 (11) 0.0043 (12)

C4 0.0342 (14) 0.0442 (15) 0.0304 (13) 0.0152 (12) −0.0065 (11) 0.0020 (11)

C5 0.0398 (14) 0.0455 (15) 0.0275 (12) 0.0210 (12) 0.0020 (10) 0.0010 (11)

C6 0.0280 (12) 0.0364 (13) 0.0348 (13) 0.0165 (11) 0.0004 (10) 0.0036 (10)

Geometric parameters (Å, º)

O1A—C11 1.196 (3) O3—N1 1.210 (3)

O1B—C11 1.308 (3) O4—N2 1.209 (3)

O1B—H11B 0.8200 O5—N2 1.211 (3)

N11—C15 1.332 (4) O6—N3 1.220 (3)

N11—C16 1.332 (3) O7—N3 1.207 (3)

N11—H11 0.8600 N1—C2 1.469 (3)

C11—C12 1.497 (4) N2—C4 1.454 (3)

C12—C16 1.377 (3) N3—C6 1.458 (3)

C12—C13 1.384 (4) C1—C6 1.423 (3)

C13—C14 1.380 (4) C1—C2 1.431 (3)

C13—H13 0.9300 C2—C3 1.372 (4)

C14—C15 1.375 (4) C3—C4 1.382 (4)

C14—H14 0.9300 C3—H3 0.9300

C15—H15 0.9300 C4—C5 1.377 (4)

C16—H16 0.9300 C5—C6 1.369 (3)

O1—C1 1.279 (3) C5—H5 0.9300

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supporting information

C11—O1B—H11B 109.5 O4—N2—O5 123.0 (3)

C15—N11—C16 122.7 (2) O4—N2—C4 119.0 (3)

C15—N11—H11 118.6 O5—N2—C4 118.0 (2)

C16—N11—H11 118.6 O7—N3—O6 123.2 (2)

O1A—C11—O1B 125.6 (3) O7—N3—C6 119.4 (2)

O1A—C11—C12 122.2 (2) O6—N3—C6 117.3 (2)

O1B—C11—C12 112.3 (2) O1—C1—C6 123.0 (2)

C16—C12—C13 119.0 (2) O1—C1—C2 124.4 (2)

C16—C12—C11 120.4 (2) C6—C1—C2 112.5 (2)

C13—C12—C11 120.6 (2) C3—C2—C1 124.1 (2)

C14—C13—C12 119.8 (2) C3—C2—N1 117.3 (2)

C14—C13—H13 120.1 C1—C2—N1 118.5 (2)

C12—C13—H13 120.1 C2—C3—C4 118.7 (2)

C15—C14—C13 119.0 (3) C2—C3—H3 120.6

C15—C14—H14 120.5 C4—C3—H3 120.6

C13—C14—H14 120.5 C5—C4—C3 121.2 (2)

N11—C15—C14 119.8 (3) C5—C4—N2 118.8 (2)

N11—C15—H15 120.1 C3—C4—N2 119.9 (2)

C14—C15—H15 120.1 C6—C5—C4 118.7 (2)

N11—C16—C12 119.7 (2) C6—C5—H5 120.7

N11—C16—H16 120.2 C4—C5—H5 120.7

C12—C16—H16 120.2 C5—C6—C1 124.7 (2)

O2—N1—O3 122.1 (3) C5—C6—N3 116.6 (2)

O2—N1—C2 119.6 (3) C1—C6—N3 118.7 (2)

O3—N1—C2 118.2 (3)

O1A—C11—C12—C16 179.4 (3) C1—C2—C3—C4 0.8 (4)

O1B—C11—C12—C16 −1.1 (4) N1—C2—C3—C4 178.8 (2)

O1A—C11—C12—C13 −1.5 (4) C2—C3—C4—C5 −1.5 (4)

O1B—C11—C12—C13 178.0 (3) C2—C3—C4—N2 177.9 (2)

C16—C12—C13—C14 0.7 (4) O4—N2—C4—C5 170.2 (3)

C11—C12—C13—C14 −178.4 (3) O5—N2—C4—C5 −9.5 (4)

C12—C13—C14—C15 −1.1 (4) O4—N2—C4—C3 −9.2 (4)

C16—N11—C15—C14 −0.1 (4) O5—N2—C4—C3 171.0 (3)

C13—C14—C15—N11 0.8 (4) C3—C4—C5—C6 2.3 (4)

C15—N11—C16—C12 −0.3 (4) N2—C4—C5—C6 −177.1 (2)

C13—C12—C16—N11 −0.1 (4) C4—C5—C6—C1 −2.6 (4)

C11—C12—C16—N11 179.1 (2) C4—C5—C6—N3 179.3 (2)

O1—C1—C2—C3 175.1 (2) O1—C1—C6—C5 −174.2 (2)

C6—C1—C2—C3 −0.9 (4) C2—C1—C6—C5 1.8 (4)

O1—C1—C2—N1 −2.9 (4) O1—C1—C6—N3 3.9 (4)

C6—C1—C2—N1 −178.9 (2) C2—C1—C6—N3 179.9 (2)

O2—N1—C2—C3 144.0 (3) O7—N3—C6—C5 −131.5 (3)

O3—N1—C2—C3 −38.5 (4) O6—N3—C6—C5 46.1 (4)

O2—N1—C2—C1 −37.9 (5) O7—N3—C6—C1 50.2 (3)

(8)

supporting information

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N11—H11···O1 0.86 1.85 2.711 (3) 174

O1B—H11B···O1i _0.82 _1.75 _{2.563 (3)} ₁₇₀

C16—H16···O7 0.93 2.55 2.962 (4) 107