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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1253.
Published online 2008 June 13. doi:  10.1107/S1600536808017066
PMCID: PMC2961823

2,2′-(3,5-Dinitro­benzyl­imino)diethanol

Abstract

The title compound, C11H15N3O6, was prepared by the reaction of (3,5-dinitro­benz­yl)methane­sulfonate with diethanol­amine. The asymmetric unit contains four crystallographically independent mol­ecules which differ primarily in their rotation about the bond between the aromatic ring and the N-diethanol unit. The mol­ecules are linked into sheets by a hydrogen-bonding network which involves all of the hydroxy groups, with only van der Waals contacts between the sheets.

Related literature

For the structure of a mononitro derivative, see: Blake et al. (1998 [triangle]). For the incorporation of N,N-bis­(2-hydroxy­ethyl)benzyl­amines in macromolecular metal complexes, see: Koizumi et al. (2005 [triangle], 2007 [triangle]). For the use of N,N-bis­(2-hydroxy­ethyl)nitro­benzyl­amines as nitro­gen mustard precursors, see: Bacherikov et al. (2005 [triangle]); Garg et al. (1976 [triangle]); Tercel et al. (1996 [triangle]); Wilson & Tishler (1951 [triangle]). For related literature, see: Crans & Boukhobza (1998 [triangle]); Kagitani et al. (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1253-scheme1.jpg

Experimental

Crystal data

  • C11H15N3O6
  • M r = 285.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1253-efi1.jpg
  • a = 12.8042 (3) Å
  • b = 14.7498 (3) Å
  • c = 15.1282 (4) Å
  • α = 104.141 (1)°
  • β = 96.371 (1)°
  • γ = 106.334 (1)°
  • V = 2608.67 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 84 (1) K
  • 0.30 × 0.30 × 0.24 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.795, T max = 0.977
  • 24719 measured reflections
  • 10576 independent reflections
  • 8548 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.101
  • S = 1.08
  • 10576 reflections
  • 753 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1995 [triangle]); cell refinement: SAINT (Bruker, 1995 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017066/hg2406sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017066/hg2406Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Higher Education Commission of Pakistan and the University of Auckland, New Zealand.

supplementary crystallographic information

Comment

N,N-Bis(2-hydroxyethyl)amines are commonly used precusors for the synthesis of N,N-bis(2-chloroethyl)amines, more commonly known as nitrogen mustards. In most cases the amine is an aniline however there are cases where the more reactive benzyl amines have been used (Bacherikov et al., 2005, Garg et al., 1976, Tercel et al., 1996, Wilson & Tishler, 1951). The use of dinitrobenzylamines, including an isomer of the title comound, N,N-bis(2-hydroxyethyl)-3,4-dinitrobenzylamine, as radiosensitizers has been reported (Kagitani et al. 1986). The dual functionality of the two free hydroxyl groups along with a basic nitrogen have seen N,N-bis(2-hydroxyethyl) benzylamines used in synthesis of numerous metal complexes including those containing vandium (Crans & Boukhobza, 1998), manganese (Koizumi et al., 2005, 2007) and iron (Koizumi et al., 2005).

The crystals contain four crystallographically independent molecules which differ primarily in their rotation about the bond between the aromatic ring and the N-diol moiety. The molecules are linked into sheets by a hydrogen bonding network which involves all of the diols, with only van der Waals contacts between the sheets. The four molecules differ in their rotation about the C1-C7 bond (torsion angles C2-C1-C7-N3 for molecules A,B,C, and D are -38, 53, 47, and -59 degrees respectively). The X-ray crystal structure of a mono-nitro derivative has been reported previously (Blake et al., 1998).

Experimental

To a solution of diethanolamine (2.69 g, 25.34 mmol) in dry THF (10 ml), at 273K, under an atmosphere of nitrogen, was added dropwise a solution of 3,5-dinitrobenzyl methanesulfonate (700 mg, 2.53 mmol) in dry THF (5 ml), and the mixture stirred at room temperature for 24 hr. The solvent was removed in vacuo, the residue diluted with ethyl acetate (30 ml) and 2M hydrochloric acid (15 ml), and the aqueous layer separated. The aqueous extract was neutralized with 4 M sodium hydroxide and extracted with ethyl acetate (3 x 40 ml). The combined organic extracts were dried (Na2SO4) and the solvent removed in vacuo to afford the crude product, which was purified by flash chromatography (9:1 dichloromethane-methanol) to afford the title compound (710 mg, 98%) as a yellow solid) which was recrystallized from dichloromethane/chloroform to give light yellow crystals (m.p. 350–351 K) suitable for X-ray crystallography. IR νmax (NaCl)/cm-1 3427, 2955, 1645, 1535. 1H NMR (400 MHz, CDCl3, δ, p.p.m.) 2.73 (4H, t, J = 10.1 Hz, N(CH2CH2OH)2), 3.67 (4H, t, J = 10.1 Hz, N(CH2CH2OH)2), 3.92 (2H, s, ArCH2N), 8.61 (2H, br s, Ar—H), 8.88 (1H, br s, Ar—H; 13C NMR (400 MHz, CDCl3, δ, p.p.m.) 55.9 (CH2, N(CH2CH2OH)2), 58.4 (CH2, ArCH2N), 59.6 (CH2, N(CH2CH2OH)2), 117.6 (CH, Ar—C), 128.7 (CH, Ar—C), 144.6 (quat., Ar—C), 148.5 (quat., Ar—C). MS m/z (FAB) 286 (MH+, 20%), 254 (M—CH2OH, 10), 154 (100). HRMS (FAB) Found MH+ 286.10436. C11H16N3O6 requires 286.10391.

Refinement

Geometrically constrained hydrogen atoms were placed in calculated positions and refined using the riding model [C—H 0.93–0.97 Å), with Uiso(H) = 1.2 or 1.5 times Ueq(C). The hydrogen atoms of the diol moieties were located in a difference Fourier map and refined individually with isotropic temperature factors.

Figures

Fig. 1.
: Structure showing 50% probability displacement ellipsoids for non-hydrogen atoms and hydrogen atoms as arbitary spheres for Molecule A (Burnett & Johnson, 1996).

Crystal data

C11H15N3O6Z = 8
Mr = 285.26F000 = 1200
Triclinic, P1Dx = 1.453 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 12.8042 (3) ÅCell parameters from 7193 reflections
b = 14.7498 (3) Åθ = 1.5–26.4º
c = 15.1282 (4) ŵ = 0.12 mm1
α = 104.141 (1)ºT = 84 (1) K
β = 96.371 (1)ºBlock, yellow
γ = 106.334 (1)º0.30 × 0.30 × 0.24 mm
V = 2608.67 (11) Å3

Data collection

Bruker SMART CCD diffractometer10576 independent reflections
Radiation source: fine-focus sealed tube8548 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 84(1) Kθmax = 26.4º
Area–detector ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)h = −16→16
Tmin = 0.795, Tmax = 0.977k = −18→17
24719 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)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0308P)2 + 1.4297P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
10576 reflectionsΔρmax = 0.33 e Å3
753 parametersΔρmin = −0.25 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 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
O1A0.22043 (12)0.88717 (13)0.52205 (10)0.0424 (4)
O2A0.13995 (11)0.97382 (10)0.61100 (9)0.0278 (3)
O3A−0.25699 (12)0.90173 (11)0.52437 (9)0.0331 (3)
O4A−0.34809 (11)0.78156 (11)0.40131 (10)0.0326 (3)
O5A0.20448 (11)0.95928 (10)0.24284 (9)0.0238 (3)
HO5A0.228 (2)0.9201 (19)0.2705 (17)0.049 (7)*
O6A0.23610 (11)0.66199 (10)0.17337 (9)0.0255 (3)
HO6A0.271 (2)0.626 (2)0.1880 (18)0.053 (8)*
N1A0.13972 (13)0.91221 (12)0.53943 (11)0.0244 (3)
N2A−0.26153 (13)0.83747 (12)0.45355 (11)0.0240 (3)
N3A0.04351 (12)0.74465 (11)0.18600 (10)0.0178 (3)
C1A−0.05692 (15)0.76440 (13)0.31650 (12)0.0183 (4)
C2A0.04103 (15)0.81190 (13)0.38236 (12)0.0184 (4)
H2A0.10860.80820.36750.022*
C3A0.03615 (15)0.86465 (13)0.47012 (12)0.0193 (4)
C4A−0.06087 (15)0.87488 (13)0.49663 (12)0.0208 (4)
H4A−0.06190.91170.55580.025*
C5A−0.15596 (15)0.82691 (13)0.42957 (12)0.0200 (4)
C6A−0.15707 (15)0.77181 (13)0.34075 (12)0.0196 (4)
H6A−0.22340.74030.29800.023*
C7A−0.05503 (15)0.70189 (13)0.22151 (12)0.0198 (4)
H7A1−0.05700.63660.22500.024*
H7A2−0.12090.69470.17840.024*
C8A0.03299 (15)0.82865 (13)0.15390 (12)0.0200 (4)
H8A1−0.00460.86450.19470.024*
H8A2−0.01240.80400.09200.024*
C9A0.14419 (15)0.89869 (13)0.15193 (12)0.0222 (4)
H9A10.18840.86070.12280.027*
H9A20.13250.94090.11420.027*
C10A0.05911 (15)0.66762 (13)0.11017 (12)0.0197 (4)
H10A0.10030.69880.06950.024*
H10B−0.01290.62490.07380.024*
C11A0.12023 (15)0.60617 (13)0.14604 (13)0.0218 (4)
H11A0.09190.58930.19880.026*
H11B0.10940.54540.09790.026*
O1B0.25171 (11)0.47448 (12)0.53893 (10)0.0359 (4)
O2B0.17606 (12)0.46382 (11)0.65871 (9)0.0324 (3)
O3B−0.21833 (12)0.36844 (12)0.62284 (9)0.0367 (4)
O4B−0.32339 (11)0.30873 (11)0.48596 (10)0.0318 (3)
O5B0.10813 (11)0.11492 (10)0.29582 (9)0.0231 (3)
HO5B0.146 (2)0.0764 (19)0.2885 (17)0.045 (7)*
O6B0.21700 (11)0.35414 (10)0.16911 (9)0.0263 (3)
HO6B0.216 (2)0.339 (2)0.2213 (19)0.057 (8)*
N1B0.17109 (13)0.45026 (11)0.57475 (11)0.0235 (3)
N2B−0.23257 (13)0.34262 (12)0.53779 (11)0.0256 (4)
N3B0.00532 (12)0.24712 (10)0.22455 (10)0.0172 (3)
C1B−0.05081 (15)0.33808 (12)0.36058 (12)0.0188 (4)
C2B0.05373 (15)0.37806 (13)0.41839 (12)0.0194 (4)
H2B0.11760.38680.39320.023*
C3B0.06095 (15)0.40445 (13)0.51366 (12)0.0194 (4)
C4B−0.03079 (15)0.39308 (13)0.55503 (12)0.0204 (4)
H4B−0.02420.41100.61930.024*
C5B−0.13292 (15)0.35360 (13)0.49594 (12)0.0199 (4)
C6B−0.14494 (15)0.32569 (13)0.39992 (12)0.0201 (4)
H6B−0.21520.29900.36240.024*
C7B−0.06015 (15)0.31195 (13)0.25610 (12)0.0207 (4)
H7B1−0.13740.27910.22620.025*
H7B2−0.03420.37190.23800.025*
C8B−0.05248 (15)0.14769 (13)0.22970 (12)0.0194 (4)
H8B1−0.11850.11850.18130.023*
H8B2−0.07630.15370.28900.023*
C9B0.01553 (15)0.07838 (13)0.21962 (12)0.0216 (4)
H9B1−0.03020.01320.21870.026*
H9B20.04190.07300.16150.026*
C10B0.02250 (15)0.24609 (14)0.12945 (12)0.0221 (4)
H10C−0.04760.23710.09100.026*
H10D0.04700.19040.10350.026*
C11B0.10692 (15)0.33980 (14)0.12651 (13)0.0239 (4)
H11C0.10580.33910.06210.029*
H11D0.08500.39550.15700.029*
O1C0.71541 (12)0.14009 (13)0.03272 (10)0.0415 (4)
O2C0.63713 (11)0.17727 (10)0.14992 (9)0.0291 (3)
O3C0.23961 (11)0.11558 (11)0.09406 (9)0.0310 (3)
O4C0.14677 (11)0.06031 (12)−0.04668 (10)0.0366 (4)
O5C0.59499 (11)−0.10538 (10)−0.23968 (9)0.0235 (3)
HO5C0.651 (2)−0.0576 (19)−0.2402 (17)0.050 (8)*
O6C0.71965 (11)0.16752 (10)−0.31633 (9)0.0238 (3)
HO6C0.742 (2)0.2218 (19)−0.2704 (17)0.049 (7)*
N1C0.63519 (13)0.15101 (12)0.06620 (11)0.0243 (3)
N2C0.23376 (13)0.09121 (11)0.01026 (10)0.0219 (3)
N3C0.50315 (12)0.04539 (11)−0.29170 (10)0.0191 (3)
C1C0.43479 (16)0.10726 (14)−0.15105 (12)0.0220 (4)
C2C0.53302 (16)0.12484 (14)−0.09012 (13)0.0233 (4)
H2C0.59960.1328−0.11130.028*
C3C0.53039 (15)0.13036 (13)0.00218 (12)0.0200 (4)
C4C0.43423 (15)0.11927 (12)0.03818 (12)0.0192 (4)
H4C0.43420.12400.10060.023*
C5C0.33861 (15)0.10077 (13)−0.02452 (12)0.0187 (4)
C6C0.33649 (15)0.09387 (13)−0.11784 (12)0.0211 (4)
H6C0.26980.0804−0.15780.025*
C7C0.43702 (17)0.10559 (15)−0.25104 (12)0.0257 (4)
H7C10.36180.0790−0.28670.031*
H7C20.46820.1725−0.25420.031*
C8C0.44264 (15)−0.05947 (14)−0.30705 (13)0.0240 (4)
H8C10.3839−0.0816−0.36140.029*
H8C20.4083−0.0668−0.25410.029*
C9C0.51532 (16)−0.12435 (14)−0.32084 (13)0.0249 (4)
H9C10.4690−0.1929−0.33880.030*
H9C20.5535−0.1139−0.37120.030*
C10C0.52879 (15)0.06382 (14)−0.37885 (12)0.0207 (4)
H10E0.46120.0610−0.41700.025*
H10F0.55420.0115−0.41200.025*
C11C0.61517 (15)0.16122 (14)−0.36682 (13)0.0242 (4)
H11E0.62430.1697−0.42740.029*
H11F0.59040.2141−0.33390.029*
O1D0.26689 (11)0.28080 (10)−0.05807 (9)0.0261 (3)
O2D0.36713 (12)0.35765 (11)−0.14003 (9)0.0328 (3)
O3D0.76729 (11)0.52132 (9)−0.00954 (9)0.0262 (3)
O4D0.83655 (11)0.44537 (11)0.07628 (10)0.0302 (3)
O5D0.36167 (11)0.54780 (10)0.21380 (9)0.0256 (3)
HO5D0.324 (2)0.4859 (19)0.2020 (17)0.046 (7)*
O6D0.24153 (11)0.31012 (10)0.33530 (9)0.0229 (3)
HO6D0.194 (2)0.250 (2)0.3221 (19)0.062 (9)*
N1D0.35569 (13)0.33096 (11)−0.06984 (10)0.0212 (3)
N2D0.75843 (13)0.46424 (11)0.03815 (10)0.0215 (3)
N3D0.45683 (12)0.41919 (11)0.29645 (10)0.0179 (3)
C1D0.53232 (15)0.36765 (12)0.15762 (12)0.0180 (4)
C2D0.43934 (15)0.34551 (12)0.08910 (12)0.0185 (4)
H2D0.36840.32180.10060.022*
C3D0.45435 (15)0.35935 (12)0.00347 (12)0.0185 (4)
C4D0.55746 (15)0.39844 (12)−0.01705 (12)0.0194 (4)
H4D0.56580.4108−0.07370.023*
C5D0.64670 (15)0.41768 (12)0.05248 (12)0.0189 (4)
C6D0.63704 (15)0.40213 (12)0.13824 (12)0.0188 (4)
H6D0.70000.41470.18230.023*
C7D0.51909 (15)0.35664 (13)0.25278 (12)0.0191 (4)
H7D10.48020.28820.24740.023*
H7D20.59170.37500.29160.023*
C8D0.51305 (15)0.52482 (13)0.30997 (13)0.0221 (4)
H8D10.55710.53250.26250.027*
H8D20.56270.55320.37000.027*
C9D0.42915 (17)0.57882 (15)0.30486 (14)0.0304 (5)
H9D10.38190.56700.34950.036*
H9D20.46780.64920.32160.036*
C10D0.43487 (15)0.40129 (14)0.38478 (12)0.0236 (4)
H10G0.41320.45510.42010.028*
H10H0.50290.40160.42030.028*
C11D0.34582 (15)0.30534 (15)0.37407 (13)0.0247 (4)
H11G0.36260.25140.33370.030*
H11H0.34280.29340.43420.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0246 (8)0.0631 (11)0.0326 (8)0.0215 (8)−0.0050 (6)−0.0022 (7)
O2A0.0309 (8)0.0278 (7)0.0182 (7)0.0051 (6)0.0003 (6)0.0019 (6)
O3A0.0320 (8)0.0423 (9)0.0269 (8)0.0182 (7)0.0108 (6)0.0040 (6)
O4A0.0181 (7)0.0400 (8)0.0367 (8)0.0072 (6)0.0055 (6)0.0078 (7)
O5A0.0234 (7)0.0207 (7)0.0262 (7)0.0066 (6)0.0014 (6)0.0070 (6)
O6A0.0241 (7)0.0250 (7)0.0283 (7)0.0125 (6)0.0006 (6)0.0060 (6)
N1A0.0230 (9)0.0280 (9)0.0199 (8)0.0073 (7)−0.0005 (7)0.0061 (7)
N2A0.0218 (9)0.0304 (9)0.0242 (8)0.0108 (7)0.0074 (7)0.0115 (7)
N3A0.0187 (8)0.0179 (7)0.0173 (7)0.0077 (6)0.0034 (6)0.0039 (6)
C1A0.0209 (9)0.0176 (9)0.0177 (9)0.0067 (7)0.0029 (7)0.0072 (7)
C2A0.0178 (9)0.0191 (9)0.0197 (9)0.0064 (7)0.0036 (7)0.0076 (7)
C3A0.0186 (9)0.0193 (9)0.0188 (9)0.0043 (7)−0.0006 (7)0.0076 (7)
C4A0.0245 (10)0.0219 (9)0.0175 (9)0.0093 (8)0.0032 (7)0.0063 (7)
C5A0.0197 (9)0.0227 (9)0.0212 (9)0.0084 (8)0.0076 (7)0.0093 (7)
C6A0.0188 (9)0.0188 (9)0.0192 (9)0.0042 (7)0.0001 (7)0.0060 (7)
C7A0.0182 (9)0.0203 (9)0.0194 (9)0.0060 (7)0.0012 (7)0.0040 (7)
C8A0.0217 (9)0.0208 (9)0.0181 (9)0.0095 (8)0.0016 (7)0.0048 (7)
C9A0.0260 (10)0.0225 (9)0.0200 (9)0.0098 (8)0.0046 (8)0.0068 (7)
C10A0.0201 (9)0.0205 (9)0.0172 (9)0.0072 (7)0.0026 (7)0.0027 (7)
C11A0.0239 (10)0.0212 (9)0.0216 (9)0.0098 (8)0.0054 (8)0.0049 (7)
O1B0.0185 (7)0.0506 (10)0.0315 (8)0.0069 (7)0.0032 (6)0.0047 (7)
O2B0.0325 (8)0.0397 (8)0.0182 (7)0.0049 (7)−0.0028 (6)0.0071 (6)
O3B0.0305 (8)0.0576 (10)0.0234 (8)0.0154 (7)0.0105 (6)0.0106 (7)
O4B0.0178 (7)0.0424 (9)0.0322 (8)0.0062 (6)0.0037 (6)0.0100 (7)
O5B0.0226 (7)0.0239 (7)0.0218 (7)0.0102 (6)0.0001 (5)0.0033 (5)
O6B0.0185 (7)0.0361 (8)0.0222 (7)0.0033 (6)0.0012 (5)0.0120 (6)
N1B0.0207 (8)0.0226 (8)0.0243 (9)0.0073 (7)−0.0006 (7)0.0034 (6)
N2B0.0236 (9)0.0304 (9)0.0242 (9)0.0093 (7)0.0065 (7)0.0089 (7)
N3B0.0186 (8)0.0181 (7)0.0160 (7)0.0072 (6)0.0051 (6)0.0046 (6)
C1B0.0218 (9)0.0153 (8)0.0201 (9)0.0091 (7)0.0024 (7)0.0034 (7)
C2B0.0186 (9)0.0183 (9)0.0214 (9)0.0080 (7)0.0044 (7)0.0036 (7)
C3B0.0192 (9)0.0163 (9)0.0218 (9)0.0073 (7)0.0003 (7)0.0039 (7)
C4B0.0247 (10)0.0177 (9)0.0192 (9)0.0084 (8)0.0031 (7)0.0049 (7)
C5B0.0204 (9)0.0181 (9)0.0239 (9)0.0086 (7)0.0069 (7)0.0071 (7)
C6B0.0193 (9)0.0159 (9)0.0225 (9)0.0057 (7)−0.0004 (7)0.0028 (7)
C7B0.0211 (9)0.0215 (9)0.0198 (9)0.0090 (8)0.0014 (7)0.0052 (7)
C8B0.0184 (9)0.0181 (9)0.0210 (9)0.0052 (7)0.0047 (7)0.0047 (7)
C9B0.0215 (10)0.0213 (9)0.0198 (9)0.0073 (8)0.0006 (7)0.0030 (7)
C10B0.0197 (9)0.0286 (10)0.0156 (9)0.0047 (8)0.0024 (7)0.0062 (7)
C11B0.0185 (9)0.0309 (10)0.0226 (9)0.0052 (8)0.0013 (7)0.0125 (8)
O1C0.0233 (8)0.0742 (12)0.0319 (8)0.0229 (8)0.0080 (6)0.0145 (8)
O2C0.0251 (7)0.0395 (8)0.0198 (7)0.0065 (6)0.0013 (6)0.0092 (6)
O3C0.0266 (8)0.0480 (9)0.0216 (7)0.0148 (7)0.0089 (6)0.0106 (6)
O4C0.0175 (7)0.0495 (9)0.0298 (8)0.0033 (7)0.0001 (6)−0.0011 (7)
O5C0.0215 (7)0.0249 (7)0.0226 (7)0.0052 (6)0.0003 (5)0.0088 (6)
O6C0.0211 (7)0.0240 (7)0.0253 (7)0.0088 (6)0.0005 (6)0.0053 (6)
N1C0.0196 (8)0.0302 (9)0.0238 (9)0.0087 (7)0.0033 (7)0.0086 (7)
N2C0.0199 (8)0.0212 (8)0.0228 (8)0.0058 (7)0.0034 (7)0.0045 (6)
N3C0.0223 (8)0.0209 (8)0.0159 (7)0.0098 (6)0.0046 (6)0.0045 (6)
C1C0.0263 (10)0.0239 (9)0.0187 (9)0.0130 (8)0.0056 (8)0.0054 (7)
C2C0.0226 (10)0.0287 (10)0.0231 (10)0.0136 (8)0.0079 (8)0.0079 (8)
C3C0.0193 (9)0.0212 (9)0.0196 (9)0.0086 (8)0.0015 (7)0.0046 (7)
C4C0.0227 (10)0.0165 (9)0.0179 (9)0.0071 (7)0.0034 (7)0.0033 (7)
C5C0.0186 (9)0.0157 (8)0.0212 (9)0.0054 (7)0.0057 (7)0.0033 (7)
C6C0.0224 (10)0.0206 (9)0.0190 (9)0.0099 (8)−0.0005 (7)0.0020 (7)
C7C0.0294 (11)0.0345 (11)0.0193 (9)0.0188 (9)0.0051 (8)0.0083 (8)
C8C0.0190 (10)0.0257 (10)0.0245 (10)0.0044 (8)−0.0016 (8)0.0077 (8)
C9C0.0289 (11)0.0221 (10)0.0200 (9)0.0079 (8)−0.0042 (8)0.0037 (7)
C10C0.0207 (10)0.0270 (10)0.0149 (8)0.0099 (8)0.0025 (7)0.0048 (7)
C11C0.0215 (10)0.0290 (10)0.0250 (10)0.0105 (8)0.0032 (8)0.0110 (8)
O1D0.0178 (7)0.0279 (7)0.0306 (7)0.0060 (6)0.0012 (6)0.0080 (6)
O2D0.0302 (8)0.0427 (9)0.0231 (7)0.0065 (7)−0.0008 (6)0.0140 (6)
O3D0.0295 (8)0.0229 (7)0.0270 (7)0.0059 (6)0.0104 (6)0.0091 (6)
O4D0.0192 (7)0.0399 (8)0.0328 (8)0.0098 (6)0.0045 (6)0.0128 (6)
O5D0.0224 (7)0.0228 (7)0.0291 (7)0.0081 (6)−0.0033 (6)0.0054 (6)
O6D0.0170 (7)0.0255 (7)0.0250 (7)0.0064 (6)0.0024 (5)0.0066 (6)
N1D0.0223 (8)0.0209 (8)0.0201 (8)0.0090 (7)0.0013 (6)0.0042 (6)
N2D0.0207 (8)0.0222 (8)0.0194 (8)0.0054 (7)0.0045 (6)0.0035 (6)
N3D0.0169 (8)0.0182 (7)0.0178 (7)0.0059 (6)0.0039 (6)0.0032 (6)
C1D0.0228 (9)0.0138 (8)0.0187 (9)0.0080 (7)0.0048 (7)0.0039 (7)
C2D0.0167 (9)0.0154 (8)0.0235 (9)0.0054 (7)0.0055 (7)0.0047 (7)
C3D0.0187 (9)0.0155 (8)0.0204 (9)0.0071 (7)0.0005 (7)0.0029 (7)
C4D0.0249 (10)0.0162 (9)0.0175 (9)0.0074 (7)0.0052 (7)0.0041 (7)
C5D0.0186 (9)0.0152 (8)0.0218 (9)0.0047 (7)0.0051 (7)0.0035 (7)
C6D0.0197 (9)0.0169 (9)0.0179 (9)0.0069 (7)0.0002 (7)0.0021 (7)
C7D0.0192 (9)0.0198 (9)0.0194 (9)0.0080 (7)0.0036 (7)0.0058 (7)
C8D0.0199 (9)0.0189 (9)0.0245 (10)0.0067 (7)−0.0008 (7)0.0024 (7)
C9D0.0289 (11)0.0254 (10)0.0307 (11)0.0126 (9)−0.0066 (9)−0.0019 (8)
C10D0.0182 (9)0.0345 (11)0.0151 (9)0.0077 (8)0.0014 (7)0.0034 (8)
C11D0.0205 (10)0.0372 (11)0.0229 (10)0.0129 (8)0.0063 (8)0.0152 (8)

Geometric parameters (Å, °)

O1A—N1A1.225 (2)O1C—N1C1.227 (2)
O2A—N1A1.2309 (19)O2C—N1C1.2257 (19)
O3A—N2A1.228 (2)O3C—N2C1.2177 (19)
O4A—N2A1.227 (2)O4C—N2C1.225 (2)
O5A—C9A1.436 (2)O5C—C9C1.421 (2)
O5A—HO5A0.89 (3)O5C—HO5C0.85 (3)
O6A—C11A1.436 (2)O6C—C11C1.432 (2)
O6A—HO6A0.84 (3)O6C—HO6C0.87 (3)
N1A—C3A1.469 (2)N1C—C3C1.473 (2)
N2A—C5A1.477 (2)N2C—C5C1.478 (2)
N3A—C7A1.465 (2)N3C—C10C1.463 (2)
N3A—C8A1.471 (2)N3C—C7C1.468 (2)
N3A—C10A1.479 (2)N3C—C8C1.469 (2)
C1A—C2A1.394 (2)C1C—C6C1.387 (3)
C1A—C6A1.398 (2)C1C—C2C1.393 (3)
C1A—C7A1.513 (2)C1C—C7C1.510 (2)
C2A—C3A1.383 (2)C2C—C3C1.383 (3)
C2A—H2A0.9300C2C—H2C0.9300
C3A—C4A1.383 (3)C3C—C4C1.385 (2)
C4A—C5A1.379 (3)C4C—C5C1.379 (2)
C4A—H4A0.9300C4C—H4C0.9300
C5A—C6A1.386 (2)C5C—C6C1.387 (2)
C6A—H6A0.9300C6C—H6C0.9300
C7A—H7A10.9700C7C—H7C10.9700
C7A—H7A20.9700C7C—H7C20.9700
C8A—C9A1.514 (3)C8C—C9C1.507 (3)
C8A—H8A10.9700C8C—H8C10.9700
C8A—H8A20.9700C8C—H8C20.9700
C9A—H9A10.9700C9C—H9C10.9700
C9A—H9A20.9700C9C—H9C20.9700
C10A—C11A1.508 (2)C10C—C11C1.501 (3)
C10A—H10A0.9700C10C—H10E0.9700
C10A—H10B0.9700C10C—H10F0.9700
C11A—H11A0.9700C11C—H11E0.9700
C11A—H11B0.9700C11C—H11F0.9700
O1B—N1B1.224 (2)O1D—N1D1.2279 (19)
O2B—N1B1.228 (2)O2D—N1D1.2290 (19)
O3B—N2B1.226 (2)O3D—N2D1.2262 (19)
O4B—N2B1.223 (2)O4D—N2D1.232 (2)
O5B—C9B1.435 (2)O5D—C9D1.435 (2)
O5B—HO5B0.84 (3)O5D—HO5D0.87 (3)
O6B—C11B1.418 (2)O6D—C11D1.425 (2)
O6B—HO6B0.87 (3)O6D—HO6D0.88 (3)
N1B—C3B1.473 (2)N1D—C3D1.472 (2)
N2B—C5B1.473 (2)N2D—C5D1.468 (2)
N3B—C7B1.470 (2)N3D—C10D1.466 (2)
N3B—C8B1.471 (2)N3D—C7D1.468 (2)
N3B—C10B1.477 (2)N3D—C8D1.473 (2)
C1B—C6B1.389 (3)C1D—C6D1.385 (2)
C1B—C2B1.396 (2)C1D—C2D1.393 (2)
C1B—C7B1.515 (2)C1D—C7D1.510 (2)
C2B—C3B1.383 (2)C2D—C3D1.385 (2)
C2B—H2B0.9300C2D—H2D0.9300
C3B—C4B1.380 (3)C3D—C4D1.386 (3)
C4B—C5B1.381 (3)C4D—C5D1.377 (3)
C4B—H4B0.9300C4D—H4D0.9300
C5B—C6B1.388 (2)C5D—C6D1.384 (2)
C6B—H6B0.9300C6D—H6D0.9300
C7B—H7B10.9700C7D—H7D10.9700
C7B—H7B20.9700C7D—H7D20.9700
C8B—C9B1.510 (2)C8D—C9D1.512 (3)
C8B—H8B10.9700C8D—H8D10.9700
C8B—H8B20.9700C8D—H8D20.9700
C9B—H9B10.9700C9D—H9D10.9700
C9B—H9B20.9700C9D—H9D20.9700
C10B—C11B1.510 (3)C10D—C11D1.506 (3)
C10B—H10C0.9700C10D—H10G0.9700
C10B—H10D0.9700C10D—H10H0.9700
C11B—H11C0.9700C11D—H11G0.9700
C11B—H11D0.9700C11D—H11H0.9700
C9A—O5A—HO5A106.4 (16)C9C—O5C—HO5C106.9 (17)
C11A—O6A—HO6A108.6 (18)C11C—O6C—HO6C107.9 (17)
O1A—N1A—O2A124.27 (16)O2C—N1C—O1C123.68 (16)
O1A—N1A—C3A117.37 (15)O2C—N1C—C3C118.17 (15)
O2A—N1A—C3A118.36 (15)O1C—N1C—C3C118.14 (15)
O4A—N2A—O3A124.24 (16)O3C—N2C—O4C124.11 (16)
O4A—N2A—C5A117.86 (15)O3C—N2C—C5C117.69 (15)
O3A—N2A—C5A117.90 (15)O4C—N2C—C5C118.20 (15)
C7A—N3A—C8A110.49 (14)C10C—N3C—C7C110.89 (14)
C7A—N3A—C10A109.39 (13)C10C—N3C—C8C110.55 (14)
C8A—N3A—C10A111.12 (13)C7C—N3C—C8C109.54 (15)
C2A—C1A—C6A119.19 (16)C6C—C1C—C2C119.03 (17)
C2A—C1A—C7A120.14 (16)C6C—C1C—C7C121.06 (17)
C6A—C1A—C7A120.60 (16)C2C—C1C—C7C119.89 (17)
C3A—C2A—C1A118.93 (16)C3C—C2C—C1C119.23 (17)
C3A—C2A—H2A120.5C3C—C2C—H2C120.4
C1A—C2A—H2A120.5C1C—C2C—H2C120.4
C2A—C3A—C4A123.74 (17)C2C—C3C—C4C123.33 (17)
C2A—C3A—N1A118.26 (16)C2C—C3C—N1C118.64 (16)
C4A—C3A—N1A118.00 (16)C4C—C3C—N1C118.01 (16)
C5A—C4A—C3A115.60 (16)C5C—C4C—C3C115.68 (16)
C5A—C4A—H4A122.2C5C—C4C—H4C122.2
C3A—C4A—H4A122.2C3C—C4C—H4C122.2
C4A—C5A—C6A123.57 (17)C4C—C5C—C6C123.32 (17)
C4A—C5A—N2A117.79 (16)C4C—C5C—N2C118.22 (15)
C6A—C5A—N2A118.62 (16)C6C—C5C—N2C118.42 (16)
C5A—C6A—C1A118.95 (16)C5C—C6C—C1C119.38 (17)
C5A—C6A—H6A120.5C5C—C6C—H6C120.3
C1A—C6A—H6A120.5C1C—C6C—H6C120.3
N3A—C7A—C1A112.46 (14)N3C—C7C—C1C111.20 (15)
N3A—C7A—H7A1109.1N3C—C7C—H7C1109.4
C1A—C7A—H7A1109.1C1C—C7C—H7C1109.4
N3A—C7A—H7A2109.1N3C—C7C—H7C2109.4
C1A—C7A—H7A2109.1C1C—C7C—H7C2109.4
H7A1—C7A—H7A2107.8H7C1—C7C—H7C2108.0
N3A—C8A—C9A112.54 (15)N3C—C8C—C9C113.34 (15)
N3A—C8A—H8A1109.1N3C—C8C—H8C1108.9
C9A—C8A—H8A1109.1C9C—C8C—H8C1108.9
N3A—C8A—H8A2109.1N3C—C8C—H8C2108.9
C9A—C8A—H8A2109.1C9C—C8C—H8C2108.9
H8A1—C8A—H8A2107.8H8C1—C8C—H8C2107.7
O5A—C9A—C8A112.84 (14)O5C—C9C—C8C112.65 (15)
O5A—C9A—H9A1109.0O5C—C9C—H9C1109.1
C8A—C9A—H9A1109.0C8C—C9C—H9C1109.1
O5A—C9A—H9A2109.0O5C—C9C—H9C2109.1
C8A—C9A—H9A2109.0C8C—C9C—H9C2109.1
H9A1—C9A—H9A2107.8H9C1—C9C—H9C2107.8
N3A—C10A—C11A112.37 (14)N3C—C10C—C11C114.25 (15)
N3A—C10A—H10A109.1N3C—C10C—H10E108.7
C11A—C10A—H10A109.1C11C—C10C—H10E108.7
N3A—C10A—H10B109.1N3C—C10C—H10F108.7
C11A—C10A—H10B109.1C11C—C10C—H10F108.7
H10A—C10A—H10B107.9H10E—C10C—H10F107.6
O6A—C11A—C10A108.68 (15)O6C—C11C—C10C111.55 (15)
O6A—C11A—H11A110.0O6C—C11C—H11E109.3
C10A—C11A—H11A110.0C10C—C11C—H11E109.3
O6A—C11A—H11B110.0O6C—C11C—H11F109.3
C10A—C11A—H11B110.0C10C—C11C—H11F109.3
H11A—C11A—H11B108.3H11E—C11C—H11F108.0
C9B—O5B—HO5B108.4 (17)C9D—O5D—HO5D107.7 (16)
C11B—O6B—HO6B109.5 (18)C11D—O6D—HO6D105.9 (18)
O1B—N1B—O2B124.05 (16)O1D—N1D—O2D123.66 (15)
O1B—N1B—C3B118.00 (15)O1D—N1D—C3D118.23 (15)
O2B—N1B—C3B117.93 (15)O2D—N1D—C3D118.10 (15)
O4B—N2B—O3B124.49 (16)O3D—N2D—O4D124.70 (16)
O4B—N2B—C5B118.26 (15)O3D—N2D—C5D117.08 (15)
O3B—N2B—C5B117.25 (15)O4D—N2D—C5D118.20 (15)
C7B—N3B—C8B108.67 (13)C10D—N3D—C7D110.61 (14)
C7B—N3B—C10B110.39 (14)C10D—N3D—C8D110.60 (14)
C8B—N3B—C10B111.62 (13)C7D—N3D—C8D112.55 (14)
C6B—C1B—C2B119.34 (16)C6D—C1D—C2D119.29 (16)
C6B—C1B—C7B120.91 (16)C6D—C1D—C7D120.34 (16)
C2B—C1B—C7B119.72 (16)C2D—C1D—C7D120.35 (16)
C3B—C2B—C1B119.07 (17)C3D—C2D—C1D118.90 (16)
C3B—C2B—H2B120.5C3D—C2D—H2D120.5
C1B—C2B—H2B120.5C1D—C2D—H2D120.5
C4B—C3B—C2B123.10 (17)C2D—C3D—C4D123.53 (17)
C4B—C3B—N1B117.71 (16)C2D—C3D—N1D118.36 (16)
C2B—C3B—N1B119.16 (16)C4D—C3D—N1D118.12 (16)
C3B—C4B—C5B116.40 (16)C5D—C4D—C3D115.22 (16)
C3B—C4B—H4B121.8C5D—C4D—H4D122.4
C5B—C4B—H4B121.8C3D—C4D—H4D122.4
C4B—C5B—C6B122.89 (17)C4D—C5D—C6D123.80 (17)
C4B—C5B—N2B117.80 (16)C4D—C5D—N2D118.53 (16)
C6B—C5B—N2B119.30 (16)C6D—C5D—N2D117.50 (16)
C5B—C6B—C1B119.20 (17)C5D—C6D—C1D119.13 (17)
C5B—C6B—H6B120.4C5D—C6D—H6D120.4
C1B—C6B—H6B120.4C1D—C6D—H6D120.4
N3B—C7B—C1B111.27 (14)N3D—C7D—C1D110.74 (14)
N3B—C7B—H7B1109.4N3D—C7D—H7D1109.5
C1B—C7B—H7B1109.4C1D—C7D—H7D1109.5
N3B—C7B—H7B2109.4N3D—C7D—H7D2109.5
C1B—C7B—H7B2109.4C1D—C7D—H7D2109.5
H7B1—C7B—H7B2108.0H7D1—C7D—H7D2108.1
N3B—C8B—C9B114.87 (15)N3D—C8D—C9D110.54 (15)
N3B—C8B—H8B1108.6N3D—C8D—H8D1109.5
C9B—C8B—H8B1108.5C9D—C8D—H8D1109.5
N3B—C8B—H8B2108.5N3D—C8D—H8D2109.5
C9B—C8B—H8B2108.5C9D—C8D—H8D2109.5
H8B1—C8B—H8B2107.5H8D1—C8D—H8D2108.1
O5B—C9B—C8B109.72 (14)O5D—C9D—C8D112.01 (15)
O5B—C9B—H9B1109.7O5D—C9D—H9D1109.2
C8B—C9B—H9B1109.7C8D—C9D—H9D1109.2
O5B—C9B—H9B2109.7O5D—C9D—H9D2109.2
C8B—C9B—H9B2109.7C8D—C9D—H9D2109.2
H9B1—C9B—H9B2108.2H9D1—C9D—H9D2107.9
N3B—C10B—C11B112.66 (15)N3D—C10D—C11D113.96 (15)
N3B—C10B—H10C109.1N3D—C10D—H10G108.8
C11B—C10B—H10C109.1C11D—C10D—H10G108.8
N3B—C10B—H10D109.1N3D—C10D—H10H108.8
C11B—C10B—H10D109.1C11D—C10D—H10H108.8
H10C—C10B—H10D107.8H10G—C10D—H10H107.7
O6B—C11B—C10B114.53 (15)O6D—C11D—C10D109.34 (15)
O6B—C11B—H11C108.6O6D—C11D—H11G109.8
C10B—C11B—H11C108.6C10D—C11D—H11G109.8
O6B—C11B—H11D108.6O6D—C11D—H11H109.8
C10B—C11B—H11D108.6C10D—C11D—H11H109.8
H11C—C11B—H11D107.6H11G—C11D—H11H108.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5A—HO5A···O6Ci0.89 (3)1.85 (3)2.7343 (19)174 (2)
O6A—HO6A···O5D0.84 (3)1.93 (3)2.7575 (19)174 (3)
O5B—HO5B···O5Aii0.84 (3)2.07 (3)2.8892 (19)165 (2)
O6B—HO6B···O6D0.87 (3)1.89 (3)2.7529 (19)170 (3)
O5C—HO5C···O5Ai0.85 (3)2.02 (3)2.8643 (19)171 (2)
O6C—HO6C···O6Ai0.87 (3)1.89 (3)2.7553 (19)170 (2)
O5D—HO5D···O6B0.87 (3)1.94 (3)2.802 (2)170 (2)
O6D—HO6D···O5B0.88 (3)1.90 (3)2.7804 (19)173 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2406).

References

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