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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Pages o1572-o1573

3-(1H-Imidazol-1-yl)propanaminium picrate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu

(Received 12 September 2013; accepted 17 September 2013; online 21 September 2013)

In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-tri­nitro­phenolate], C6H12N3+·C6H2N3O7, there are five independent cation–anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the amino­propyl group nearly at right angles to the mean plane of the imidazole ring showing C—N—C—C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H⋯O cation–anion and N—H⋯N cation–cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C—H⋯O cation–anion inter­actions occur.

Related literature

For pharmacological properties of imidazole compounds, see: Lombardino & Wiseman (1974[Lombardino, J. G. & Wiseman, E. H. (1974). J. Med. Chem. 17, 1182-1188.]). For applications of substituted imidazoles, see: Maier et al. (1989a[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4 820 335.],b[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.]). For imidazole derivatives as anti­cancer agents, see: Krezel (1998[Krezel, I. (1998). Farmaco, 53, 342-345.]). For electrostatic or hydrogen-bonding inter­actions in picric acid charge-transfer complexes, see: In et al. (1997[In, Y., Nagata, H., Doi, M., Ishida, T. & Wakahara, A. (1997). Acta Cryst. C53, 367-369.]). For imidazolium-based cation picrate salts as good candidates for energetic ionic salts, see: Jin et al. (2005[Jin, C. M., Ye, C., Piekarski, C., Twamley, B. & Shreeve, J. M. (2005). Eur. J. Inorg. Chem. pp. 3760-3767.]). For the crystal structure of imidazolium picrate, see: Soriano-García et al. (1990[Soriano-García, M., Schatz-Levine, M., Toscano, R. A. & Villena Iribe, R. (1990). Acta Cryst. C46, 1556-1558.]) and for the structures of picrates of some other imidazole deriv­atives, see: Du & Zhao (2003[Du, M. & Zhao, X.-J. (2003). Acta Cryst. E59, o1898-o1900.]); Dutkiewicz et al. (2011[Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235.]); MacDonald et al. (2005[MacDonald, J., Yigit, M. V. & Mychajlonka, K. (2005). Cryst. Growth Des. 5, 2248-2255.]); Nardelli et al. (1987[Nardelli, M., Pelizzi, G., Vitali, F., Bordi, F., Plazzi, P. V. & Vitali, T. (1987). Acta Cryst. C43, 507-514.]); Pi et al. (2009[Pi, M., Liu, X.-L., Xu, J.-J. & Jin, C.-M. (2009). Acta Cryst. E65, o2386.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C6H12N3+·C6H2N3O7

  • Mr = 354.29

  • Monoclinic, P 21 /n

  • a = 11.98275 (18) Å

  • b = 38.5234 (6) Å

  • c = 16.4239 (2) Å

  • β = 94.1970 (14)°

  • V = 7561.2 (2) Å3

  • Z = 20

  • Cu Kα radiation

  • μ = 1.13 mm−1

  • T = 173 K

  • 0.21 × 0.17 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.870, Tmax = 1.000

  • 52087 measured reflections

  • 14795 independent reflections

  • 12167 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.02

  • 14795 reflections

  • 1197 parameters

  • 12 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N6A—H6AA⋯O3Ei 0.85 (2) 2.06 (2) 2.8943 (18) 167.5 (18)
N6A—H6AB⋯O3Dii 0.91 (2) 2.08 (2) 2.8671 (18) 143.1 (16)
N6A—H6AB⋯O4Dii 0.91 (2) 2.25 (2) 2.961 (2) 134.6 (15)
N6A—H6AC⋯N4C 0.95 (2) 1.87 (2) 2.8157 (19) 172.5 (18)
N6B—H6BA⋯O3Biii 0.92 (2) 2.117 (19) 2.8728 (17) 138.5 (15)
N6B—H6BA⋯O4Biii 0.92 (2) 2.268 (19) 3.006 (2) 136.6 (15)
N6B—H6BB⋯O3B 0.89 (2) 2.00 (2) 2.8502 (17) 161.0 (19)
N6B—H6BC⋯N4Aiv 0.92 (2) 1.88 (2) 2.7988 (19) 173.4 (17)
N6C—H6CA⋯O2Cv 0.85 (2) 2.305 (18) 2.8334 (19) 120.9 (15)
N6C—H6CA⋯O3Cv 0.85 (2) 2.10 (2) 2.8944 (18) 155.4 (17)
N6C—H6CB⋯O3Avi 0.89 (2) 2.174 (19) 2.9145 (18) 140.2 (16)
N6C—H6CB⋯O4Avi 0.89 (2) 2.270 (19) 2.986 (2) 137.3 (15)
N6C—H6CC⋯N4Dvi 0.92 (2) 1.91 (2) 2.8179 (19) 167.6 (17)
N6D—H6DA⋯O2Avii 0.89 (2) 2.361 (19) 2.9631 (19) 124.9 (15)
N6D—H6DA⋯O3Avii 0.89 (2) 2.06 (2) 2.8340 (17) 145.0 (16)
N6D—H6DB⋯O3Cvi 0.89 (2) 2.16 (2) 2.9171 (17) 142.0 (17)
N6D—H6DB⋯O4Cvi 0.89 (2) 2.27 (2) 2.9323 (19) 130.5 (16)
N6D—H6DC⋯N4E 0.89 (2) 1.91 (2) 2.7932 (19) 174.0 (17)
N6E—H6EA⋯O2Dviii 0.91 (2) 2.32 (2) 2.973 (2) 128.7 (17)
N6E—H6EA⋯O3Dviii 0.91 (2) 2.06 (2) 2.8527 (18) 145.4 (18)
N6E—H6EB⋯O3E 0.87 (2) 2.19 (2) 2.9056 (18) 139.6 (17)
N6E—H6EB⋯O4E 0.87 (2) 2.33 (2) 3.010 (2) 135.3 (16)
N6E—H6EC⋯N4Bviii 0.93 (2) 1.85 (2) 2.7750 (19) 174.0 (19)
C8A—H8A⋯O2Bix 0.95 2.46 3.0887 (19) 123
C9A—H9A⋯O5E 0.95 2.43 3.243 (2) 144
C12A—H12B⋯O7Aix 0.99 2.46 3.313 (2) 145
C9B—H9B⋯O5Bi 0.95 2.37 3.224 (2) 150
C12B—H12D⋯O7Cvi 0.99 2.47 3.335 (2) 145
C8C—H8C⋯O5Cvi 0.95 2.33 3.194 (2) 152
C9C—H9C⋯O2Ei 0.95 2.49 3.105 (2) 123
C7D—H7D⋯O5Avi 0.95 2.35 3.233 (2) 155
C11D—H11H⋯O6Avi 0.99 2.55 3.421 (2) 147
C12D—H12G⋯O6Bvii 0.99 2.43 3.238 (2) 139
C9E—H9E⋯O5Dii 0.95 2.27 3.162 (6) 156
C9E—H9E⋯O5DAii 0.95 2.56 3.357 (17) 141
C12E—H12I⋯O6Eviii 0.99 2.34 3.186 (2) 142
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z; (iv) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) -x+2, -y+1, -z+1; (vi) -x+1, -y+1, -z+1; (vii) -x, -y+1, -z+1; (viii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ix) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

Compounds with an imidazole ring system have many pharmacological properties and play important roles in biochemical processes (Lombardino & Wiseman, 1974). Many imidazole derivatives are characterized as inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989a,b). Imidazole derivatives are also used as potential anticancer agents (Krezel, 1998) and display a broad spectrum of pharmacological activities. It is well known that picric acid forms charge transfer molecular complexes with a number of aromatic compounds such as aromatic amines through electrostatic or hydrogen bonding interactions (In et al., 1997). Picric acid is a polynitrogen compound with explosive character and imidazolium-based cation picrate salts are good candidates for energetic ionic salts (Jin et al., 2005).

The crystal structures of some imidazolium picrates have been reported, for instance imidazolium picrate itself (Soriano-García et al., 1990), also two solvates (hydrate and ethanolate) of 2-aminohistamine dipicrate (Nardelli et al., 1987), 4-hydroxy methylimidazolium picrate (Du & Zhao, 2003), two polymorphs of betaine bis(diimidazolium) dipicrate (MacDonald et al., 2005) and 3-benzyl-1-methyl-imidazolium picrate (Pi et al., 2009). Recently, we have reported the crystal structure of 2-methylimidazolium picrate (Dutkiewicz et al., 2011).

In view of the importance of imidazoles, this paper reports the crystal structure of the title salt, C6H12N3+ . C6H2N3O7-, (I).

In (I), there are five cation-anion independent pairs (A, B, C, D, E) in the asymmetric unit. For clarity only the C cation-anion pair is displayed in Fig. 1. In the cation the ammonium group is protonated with the aminopropyl group nearly at right angles to the imidazole ring showing C/N/C/C torsion angles ranging from 79.6 (2)° to 99.79 (19)° in the five cations. Bond lengths are in normal ranges (Allen et al., 1987). The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to phenolate oxygen of 26.0 (2)°, 37,3(7)° (A); 28,9(5)°, 35.3 (1)° (B); 34.7 (7)°, 36.9 (7)° (C); 14.7 (4)°, 36.9 (2)° (D); 33.1 (1)°, 35.4 (3)° (E). In contrast the nitro groups in the para positions lie much closer to the aromatic ring plane with angles 1.8 (3)° (A); 3.5 (3)° (B); 6.03° (C); 2.1 (3)° (D); 7.7 (1)° (E), respectively. Disorder is observed in atom O5D, an ortho nitro group in anion D, with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H···O cation-anion and N—H···N cation-cation hydrogen bonds (Table 1) are observed linking the ions into chains along [0 1 0] (Fig. 2). In addition, weak C—H···O cation-anion intermolecular interactions also contribute to packing stability.

Related literature top

For pharmacological properties of imidazole compounds, see: Lombardino & Wiseman (1974). For applications of substituted imidazoles, see: Maier et al. (1989a,b). For imidazole derivatives as anticancer agents, see: Krezel (1998). For electrostatic or hydrogen-bonding interactions in picric acid charge-transfer complexes, see: In et al. (1997). For imidazolium-based cation picrate salts as good candidates for energetic ionic salts, see: Jin et al. (2005). For the crystal structure of imidazolium picrate, see: Soriano-García et al. (1990) and for the structures of picrates of some other imidazole derivatives, see: Du & Zhao (2003); Dutkiewicz et al. (2011); MacDonald et al. (2005); Nardelli et al. (1987); Pi et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Commercially available 1-(3-aminopropyl)imidazole (0.5 g, 3.99 mmol) and picric acid (1.19 g, 3.99 mmol) were dissolved in 10 ml of ethanol and stirred for 5 minutes at room temperature. After 30 mins, crystals were formed on evaporation of ethanol (m.p.: 370–373 K).

Refinement top

H6AA, H6AB, H6AC, H6BA, H6BB, H6BC, H6CA, H6CB, H6CC, H6DA, H6DB, H6DC, H6EA, H6EB, H6EC, were located by a difference map and refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (aromatic) or 0.99Å (CH2). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2) times Ueq of the parent atom. Disorder is observed in atom O5D of anion D with an occupancy ratio of 0.53 (5):0.47 (5).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of one of five independent cation (C6H12N3+ ) and anion (C6H2N3O7-) pairs (C) in the asymmetric unit of (I), for clarity, showing the atom labeling scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Molecular packing for (I) viewed along the c axis. Dashed lines indicate N—H···O cation–anion and N—H···N cation-cation hydrogen bonds, dahed lines, linking the ions into chains along [0 1 0]. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.
3-(1H-Imidazol-1-yl)propanaminium 2,4,6-trinitrophenolate top
Crystal data top
C6H12N3+·C6H2N3O7F(000) = 3680
Mr = 354.29Dx = 1.556 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 11.98275 (18) ÅCell parameters from 17325 reflections
b = 38.5234 (6) Åθ = 3.4–72.3°
c = 16.4239 (2) ŵ = 1.13 mm1
β = 94.1970 (14)°T = 173 K
V = 7561.2 (2) Å3Irregular, clear yellow
Z = 200.21 × 0.17 × 0.08 mm
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
14795 independent reflections
Radiation source: Enhance (Cu) X-ray Source12167 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.032
ω scansθmax = 72.5°, θmin = 3.5°
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
h = 914
Tmin = 0.870, Tmax = 1.000k = 4746
52087 measured reflectionsl = 2020
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0585P)2 + 2.3598P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.51 e Å3
14795 reflectionsΔρmin = 0.29 e Å3
1197 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
12 restraintsExtinction coefficient: 0.000142 (14)
Crystal data top
C6H12N3+·C6H2N3O7V = 7561.2 (2) Å3
Mr = 354.29Z = 20
Monoclinic, P21/nCu Kα radiation
a = 11.98275 (18) ŵ = 1.13 mm1
b = 38.5234 (6) ÅT = 173 K
c = 16.4239 (2) Å0.21 × 0.17 × 0.08 mm
β = 94.1970 (14)°
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
14795 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
12167 reflections with I > 2σ(I)
Tmin = 0.870, Tmax = 1.000Rint = 0.032
52087 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04212 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.51 e Å3
14795 reflectionsΔρmin = 0.29 e Å3
1197 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.06660 (12)0.70857 (4)0.28122 (10)0.0543 (4)
O2A0.03780 (11)0.68796 (4)0.40019 (10)0.0477 (4)
O3A0.11234 (9)0.62090 (3)0.40908 (7)0.0296 (3)
O4A0.21360 (12)0.56043 (3)0.37863 (10)0.0491 (4)
O5A0.39119 (12)0.56511 (4)0.39119 (12)0.0636 (5)
O6A0.55513 (10)0.65993 (4)0.25325 (8)0.0417 (3)
O7A0.46158 (11)0.70758 (4)0.23205 (9)0.0446 (3)
N1A0.09133 (12)0.68950 (4)0.33963 (10)0.0329 (3)
N2A0.29916 (12)0.57781 (4)0.37670 (9)0.0321 (3)
N3A0.47021 (12)0.67773 (4)0.25701 (9)0.0318 (3)
C1A0.27832 (13)0.68191 (4)0.29857 (10)0.0259 (3)
H1A0.27290.70460.27610.031*
C2A0.19050 (12)0.66773 (4)0.33624 (10)0.0245 (3)
C3A0.18956 (12)0.63312 (4)0.37119 (9)0.0224 (3)
C4A0.29093 (13)0.61429 (4)0.35572 (9)0.0246 (3)
C5A0.38185 (13)0.62869 (4)0.32185 (9)0.0260 (3)
H5A0.44820.61550.31780.031*
C6A0.37572 (13)0.66236 (4)0.29393 (9)0.0260 (3)
O1B0.41038 (10)0.62930 (3)0.10159 (8)0.0377 (3)
O2B0.50153 (9)0.58259 (3)0.13563 (9)0.0385 (3)
O3B0.37850 (9)0.52841 (3)0.06265 (7)0.0261 (2)
O4B0.25989 (12)0.47144 (3)0.10774 (9)0.0432 (3)
O5B0.08374 (12)0.48134 (4)0.08146 (10)0.0571 (4)
O6B0.05515 (10)0.58211 (4)0.20725 (8)0.0392 (3)
O7B0.04050 (10)0.62992 (3)0.20991 (8)0.0386 (3)
N1B0.02960 (11)0.59876 (4)0.19519 (8)0.0299 (3)
N2B0.17976 (12)0.49122 (4)0.10008 (9)0.0331 (3)
N3B0.41401 (11)0.59841 (3)0.11880 (8)0.0243 (3)
C1B0.22192 (12)0.59790 (4)0.15207 (9)0.0232 (3)
H1B0.22970.62190.16480.028*
C2B0.12167 (13)0.58070 (4)0.16165 (9)0.0255 (3)
C3B0.10926 (13)0.54597 (4)0.14262 (9)0.0253 (3)
H3B0.04020.53450.14900.030*
C4B0.19756 (13)0.52809 (4)0.11443 (9)0.0249 (3)
C5B0.30432 (12)0.54352 (4)0.09843 (9)0.0209 (3)
C6B0.30933 (12)0.57958 (4)0.12386 (9)0.0214 (3)
O1C0.93330 (11)0.49777 (4)0.71717 (9)0.0459 (3)
O2C0.95844 (11)0.51289 (4)0.59358 (10)0.0504 (4)
O3C0.85836 (9)0.57635 (3)0.56438 (7)0.0274 (2)
O4C0.70931 (11)0.63065 (3)0.55889 (8)0.0392 (3)
O5C0.54488 (11)0.60950 (4)0.52653 (10)0.0488 (4)
O6C0.42608 (9)0.52706 (3)0.72080 (8)0.0357 (3)
O7C0.53457 (10)0.48321 (3)0.75141 (8)0.0400 (3)
N1C0.90358 (11)0.51276 (4)0.65333 (9)0.0307 (3)
N2C0.64000 (12)0.60737 (4)0.56060 (9)0.0306 (3)
N3C0.51685 (11)0.51198 (4)0.72106 (8)0.0287 (3)
C1C0.71259 (13)0.51435 (4)0.68752 (9)0.0237 (3)
H1C0.72740.49370.71800.028*
C2C0.79609 (12)0.53034 (4)0.64799 (9)0.0230 (3)
C3C0.78325 (12)0.56224 (4)0.60164 (9)0.0217 (3)
C4C0.67031 (13)0.57559 (4)0.60354 (9)0.0243 (3)
C5C0.58477 (13)0.55929 (4)0.63995 (9)0.0255 (3)
H5C0.51160.56890.63610.031*
C6C0.60648 (12)0.52896 (4)0.68195 (9)0.0241 (3)
O1D0.43842 (13)0.41609 (4)0.17945 (13)0.0753 (6)
O2D0.45803 (12)0.38759 (4)0.06991 (9)0.0483 (4)
O3D0.39104 (9)0.32112 (3)0.09394 (8)0.0321 (3)
O4D0.27366 (16)0.26401 (4)0.11869 (13)0.0756 (6)
O5D0.1088 (5)0.2689 (2)0.132 (2)0.074 (6)0.53 (5)
O5DA0.1161 (9)0.2685 (2)0.1739 (14)0.051 (3)0.47 (5)
O6D0.04727 (10)0.37181 (4)0.23998 (8)0.0417 (3)
O7D0.04676 (10)0.41989 (3)0.24429 (8)0.0392 (3)
N1D0.41073 (12)0.39325 (4)0.13245 (10)0.0335 (3)
N2D0.19780 (13)0.28171 (4)0.13810 (9)0.0346 (3)
N3D0.03733 (11)0.38876 (4)0.22938 (8)0.0310 (3)
C1D0.22787 (13)0.38939 (4)0.18260 (10)0.0259 (3)
H1D0.23490.41320.19720.031*
C2D0.31297 (13)0.37241 (4)0.14767 (10)0.0246 (3)
C3D0.31268 (12)0.33593 (4)0.12588 (9)0.0237 (3)
C4D0.21039 (13)0.31897 (4)0.14756 (9)0.0258 (3)
C5D0.12236 (13)0.33613 (4)0.17907 (10)0.0271 (3)
H5D0.05590.32390.18890.033*
C6D0.13078 (13)0.37097 (4)0.19620 (10)0.0266 (3)
O1E0.08024 (11)0.32801 (3)0.38651 (11)0.0522 (4)
O2E0.00509 (10)0.27786 (3)0.36309 (9)0.0387 (3)
O3E0.14077 (9)0.23016 (3)0.45016 (7)0.0273 (2)
O4E0.28681 (12)0.17609 (3)0.42987 (9)0.0453 (3)
O5E0.45292 (11)0.19515 (4)0.46414 (11)0.0559 (4)
O6E0.56176 (10)0.29016 (4)0.29897 (8)0.0429 (3)
O7E0.45539 (11)0.33582 (4)0.29169 (8)0.0457 (3)
N1E0.08694 (11)0.29654 (3)0.37717 (8)0.0274 (3)
N2E0.35637 (12)0.19938 (4)0.43450 (10)0.0344 (3)
N3E0.47330 (12)0.30510 (4)0.30897 (8)0.0337 (3)
C1E0.28020 (13)0.30019 (4)0.34811 (9)0.0261 (3)
H1E0.26580.32330.32980.031*
C2E0.19720 (12)0.28065 (4)0.37890 (9)0.0236 (3)
C3E0.21231 (12)0.24610 (4)0.41326 (9)0.0221 (3)
C4E0.32526 (13)0.23366 (4)0.40462 (10)0.0249 (3)
C5E0.40861 (13)0.25255 (4)0.37280 (9)0.0265 (3)
H5E0.48140.24300.37050.032*
C6E0.38536 (13)0.28565 (4)0.34421 (9)0.0270 (3)
N4A0.75790 (11)0.09105 (3)0.43652 (9)0.0303 (3)
N5A0.69358 (11)0.14260 (3)0.39781 (8)0.0244 (3)
N6A0.90342 (12)0.23186 (3)0.47233 (9)0.0253 (3)
H6AA0.9724 (18)0.2348 (5)0.4655 (12)0.032 (5)*
H6AB0.8939 (15)0.2239 (5)0.5237 (13)0.030 (5)*
H6AC0.8659 (16)0.2535 (5)0.4655 (12)0.034 (5)*
C7A0.66412 (14)0.09844 (4)0.47645 (10)0.0295 (3)
H7A0.63230.08350.51460.035*
C8A0.77269 (13)0.11818 (4)0.38983 (11)0.0276 (3)
H8A0.83190.12030.35470.033*
C9A0.62334 (13)0.13017 (4)0.45358 (10)0.0279 (3)
H9A0.55950.14140.47230.033*
C10A0.68255 (14)0.17569 (4)0.35409 (10)0.0284 (3)
H10A0.60250.18010.33830.034*
H10B0.72240.17420.30350.034*
C11A0.72981 (13)0.20599 (4)0.40554 (11)0.0271 (3)
H11A0.70110.22810.38120.033*
H11B0.70380.20420.46120.033*
C12A0.85708 (13)0.20646 (4)0.41082 (11)0.0277 (3)
H12A0.88560.18300.42550.033*
H12B0.88300.21250.35670.033*
N4B0.73741 (12)0.39002 (3)0.09045 (10)0.0337 (3)
N5B0.80676 (11)0.44049 (3)0.13254 (8)0.0250 (3)
N6B0.61280 (11)0.53074 (3)0.04321 (9)0.0245 (3)
H6BA0.6219 (15)0.5212 (5)0.0074 (12)0.029 (5)*
H6BB0.5412 (18)0.5353 (5)0.0484 (12)0.040 (6)*
H6BC0.6517 (15)0.5514 (5)0.0468 (11)0.029 (5)*
C7B0.83655 (14)0.39557 (4)0.05633 (11)0.0305 (4)
H7B0.86990.38000.02040.037*
C8B0.72217 (14)0.41758 (4)0.13569 (11)0.0309 (4)
H8B0.65920.42090.16680.037*
C9B0.88023 (13)0.42658 (4)0.08124 (10)0.0280 (3)
H9B0.94810.43670.06620.034*
C10B0.81931 (14)0.47403 (4)0.17389 (10)0.0288 (3)
H10C0.89900.47760.19240.035*
H10D0.77570.47390.22280.035*
C11B0.77981 (13)0.50414 (4)0.11863 (10)0.0265 (3)
H11C0.81140.52610.14160.032*
H11D0.80800.50080.06400.032*
C12B0.65295 (13)0.50676 (4)0.11003 (10)0.0269 (3)
H12C0.62090.48340.09890.032*
H12D0.62600.51510.16210.032*
N4C0.77635 (12)0.29279 (3)0.44507 (10)0.0333 (3)
N5C0.71008 (11)0.34335 (3)0.40054 (9)0.0267 (3)
N6C0.91077 (12)0.43386 (3)0.47087 (9)0.0238 (3)
H6CA0.9797 (17)0.4372 (5)0.4660 (11)0.027 (5)*
H6CB0.9011 (15)0.4268 (5)0.5215 (12)0.026 (5)*
H6CC0.8729 (16)0.4547 (5)0.4643 (12)0.034 (5)*
C7C0.68308 (15)0.30101 (4)0.48517 (11)0.0326 (4)
H7C0.65230.28700.52550.039*
C8C0.64165 (14)0.33207 (4)0.45851 (11)0.0310 (4)
H8C0.57790.34370.47640.037*
C9C0.78943 (14)0.31884 (4)0.39487 (11)0.0302 (4)
H9C0.84780.32020.35890.036*
C10C0.69767 (14)0.37533 (4)0.35294 (11)0.0300 (4)
H10E0.61760.37880.33550.036*
H10F0.73900.37300.30320.036*
C11C0.74117 (13)0.40700 (4)0.40111 (11)0.0278 (3)
H11E0.71230.42830.37330.033*
H11F0.71290.40640.45620.033*
C12C0.86828 (13)0.40808 (4)0.40902 (10)0.0273 (3)
H12E0.89750.38480.42470.033*
H12F0.89610.41410.35550.033*
N4D0.22010 (12)0.50702 (3)0.56986 (9)0.0317 (3)
N5D0.28930 (11)0.46050 (3)0.63391 (8)0.0258 (3)
N6D0.11287 (12)0.36876 (3)0.55463 (9)0.0233 (3)
H6DA0.0399 (17)0.3640 (5)0.5526 (11)0.029 (5)*
H6DB0.1314 (16)0.3766 (5)0.5062 (13)0.035 (5)*
H6DC0.1483 (15)0.3488 (5)0.5657 (11)0.028 (5)*
C7D0.36432 (14)0.47005 (4)0.57872 (10)0.0298 (3)
H7D0.43290.45890.56930.036*
C8D0.20416 (13)0.48345 (4)0.62573 (10)0.0277 (3)
H8D0.14030.48270.65670.033*
C9D0.32091 (14)0.49861 (4)0.54037 (11)0.0318 (4)
H9D0.35530.51110.49900.038*
C10D0.29807 (14)0.43027 (4)0.68810 (10)0.0289 (3)
H10G0.24830.43360.73300.035*
H10H0.37580.42840.71260.035*
C11D0.26634 (13)0.39670 (4)0.64306 (10)0.0271 (3)
H11G0.30860.39500.59370.033*
H11H0.28750.37670.67870.033*
C12D0.14198 (13)0.39512 (4)0.61840 (10)0.0282 (3)
H12G0.10130.38980.66720.034*
H12H0.11670.41820.59790.034*
N4E0.23642 (12)0.30890 (4)0.59484 (10)0.0341 (3)
N5E0.30112 (11)0.26041 (3)0.65175 (8)0.0264 (3)
N6E0.11830 (12)0.17068 (3)0.55652 (9)0.0244 (3)
H6EA0.0441 (19)0.1656 (5)0.5537 (13)0.040 (6)*
H6EB0.1349 (16)0.1796 (5)0.5102 (13)0.031 (5)*
H6EC0.1545 (17)0.1495 (5)0.5656 (12)0.038 (5)*
C7E0.34032 (15)0.30216 (4)0.56911 (11)0.0334 (4)
H7E0.37820.31630.53260.040*
C8E0.21567 (14)0.28319 (4)0.64442 (11)0.0308 (4)
H8E0.14880.28100.67160.037*
C9E0.38128 (14)0.27238 (4)0.60320 (11)0.0314 (4)
H9E0.45140.26190.59520.038*
C10E0.30688 (15)0.22809 (4)0.69875 (10)0.0309 (4)
H10I0.25620.22980.74360.037*
H10J0.38400.22490.72350.037*
C11E0.27412 (14)0.19658 (4)0.64595 (11)0.0289 (3)
H11I0.31440.19740.59550.035*
H11J0.29700.17510.67590.035*
C12E0.14910 (13)0.19551 (4)0.62346 (10)0.0285 (3)
H12I0.11010.18890.67220.034*
H12J0.12330.21900.60660.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0449 (8)0.0491 (9)0.0694 (10)0.0187 (7)0.0076 (7)0.0317 (8)
O2A0.0382 (7)0.0381 (7)0.0701 (10)0.0121 (6)0.0267 (7)0.0157 (7)
O3A0.0234 (6)0.0277 (6)0.0385 (7)0.0032 (4)0.0086 (5)0.0102 (5)
O4A0.0497 (8)0.0259 (7)0.0754 (10)0.0009 (6)0.0289 (7)0.0023 (6)
O5A0.0416 (8)0.0411 (8)0.1072 (14)0.0184 (7)0.0008 (8)0.0171 (9)
O6A0.0233 (6)0.0594 (9)0.0435 (7)0.0038 (6)0.0105 (5)0.0068 (6)
O7A0.0383 (7)0.0441 (8)0.0531 (8)0.0064 (6)0.0156 (6)0.0134 (6)
N1A0.0243 (7)0.0262 (7)0.0490 (9)0.0023 (6)0.0077 (6)0.0102 (6)
N2A0.0376 (8)0.0271 (7)0.0323 (8)0.0070 (6)0.0076 (6)0.0011 (6)
N3A0.0255 (7)0.0429 (9)0.0275 (7)0.0041 (6)0.0058 (6)0.0023 (6)
C1A0.0260 (8)0.0261 (8)0.0257 (8)0.0018 (6)0.0018 (6)0.0033 (6)
C2A0.0202 (7)0.0255 (8)0.0278 (8)0.0017 (6)0.0018 (6)0.0035 (6)
C3A0.0203 (7)0.0244 (8)0.0221 (7)0.0002 (6)0.0003 (6)0.0012 (6)
C4A0.0261 (8)0.0250 (8)0.0226 (7)0.0023 (6)0.0011 (6)0.0014 (6)
C5A0.0216 (8)0.0341 (9)0.0227 (8)0.0043 (6)0.0026 (6)0.0016 (6)
C6A0.0219 (8)0.0336 (9)0.0229 (8)0.0027 (6)0.0045 (6)0.0003 (6)
O1B0.0373 (7)0.0221 (6)0.0538 (8)0.0069 (5)0.0042 (6)0.0045 (5)
O2B0.0200 (6)0.0304 (6)0.0647 (9)0.0008 (5)0.0011 (5)0.0070 (6)
O3B0.0235 (5)0.0231 (5)0.0322 (6)0.0030 (4)0.0061 (4)0.0062 (4)
O4B0.0530 (8)0.0236 (6)0.0551 (8)0.0036 (6)0.0182 (7)0.0002 (6)
O5B0.0431 (8)0.0511 (9)0.0791 (11)0.0284 (7)0.0180 (8)0.0235 (8)
O6B0.0230 (6)0.0589 (8)0.0369 (7)0.0004 (6)0.0098 (5)0.0014 (6)
O7B0.0309 (6)0.0438 (8)0.0407 (7)0.0103 (5)0.0015 (5)0.0134 (6)
N1B0.0236 (7)0.0428 (8)0.0231 (7)0.0060 (6)0.0000 (5)0.0044 (6)
N2B0.0387 (8)0.0298 (8)0.0325 (8)0.0143 (6)0.0147 (6)0.0058 (6)
N3B0.0232 (7)0.0208 (6)0.0295 (7)0.0022 (5)0.0050 (5)0.0039 (5)
C1B0.0250 (8)0.0230 (7)0.0212 (7)0.0012 (6)0.0017 (6)0.0012 (6)
C2B0.0207 (7)0.0349 (9)0.0208 (7)0.0031 (6)0.0014 (6)0.0009 (6)
C3B0.0214 (7)0.0341 (9)0.0206 (7)0.0067 (6)0.0031 (6)0.0010 (6)
C4B0.0278 (8)0.0252 (8)0.0220 (7)0.0067 (6)0.0037 (6)0.0015 (6)
C5B0.0199 (7)0.0226 (7)0.0201 (7)0.0010 (6)0.0011 (5)0.0007 (6)
C6B0.0195 (7)0.0222 (7)0.0224 (7)0.0029 (6)0.0013 (6)0.0006 (6)
O1C0.0330 (7)0.0508 (8)0.0523 (8)0.0039 (6)0.0072 (6)0.0256 (7)
O2C0.0337 (7)0.0504 (8)0.0702 (10)0.0179 (6)0.0259 (7)0.0294 (7)
O3C0.0223 (5)0.0256 (6)0.0351 (6)0.0003 (4)0.0075 (5)0.0091 (5)
O4C0.0440 (7)0.0218 (6)0.0542 (8)0.0026 (5)0.0191 (6)0.0055 (5)
O5C0.0311 (7)0.0484 (8)0.0668 (10)0.0159 (6)0.0038 (6)0.0232 (7)
O6C0.0219 (6)0.0472 (7)0.0388 (7)0.0020 (5)0.0091 (5)0.0035 (6)
O7C0.0344 (7)0.0417 (7)0.0449 (7)0.0061 (5)0.0092 (6)0.0163 (6)
N1C0.0206 (7)0.0277 (7)0.0439 (8)0.0014 (5)0.0019 (6)0.0150 (6)
N2C0.0305 (8)0.0259 (7)0.0371 (8)0.0084 (6)0.0140 (6)0.0057 (6)
N3C0.0249 (7)0.0363 (8)0.0253 (7)0.0066 (6)0.0051 (5)0.0024 (6)
C1C0.0250 (8)0.0239 (7)0.0219 (7)0.0031 (6)0.0010 (6)0.0031 (6)
C2C0.0202 (7)0.0249 (8)0.0236 (7)0.0009 (6)0.0004 (6)0.0019 (6)
C3C0.0213 (7)0.0227 (7)0.0213 (7)0.0017 (6)0.0022 (6)0.0017 (6)
C4C0.0267 (8)0.0215 (7)0.0249 (8)0.0021 (6)0.0038 (6)0.0015 (6)
C5C0.0215 (7)0.0290 (8)0.0267 (8)0.0024 (6)0.0057 (6)0.0011 (6)
C6C0.0222 (8)0.0288 (8)0.0218 (7)0.0051 (6)0.0054 (6)0.0000 (6)
O1D0.0514 (9)0.0660 (11)0.1123 (15)0.0325 (8)0.0321 (10)0.0561 (11)
O2D0.0426 (8)0.0415 (8)0.0634 (10)0.0059 (6)0.0214 (7)0.0024 (7)
O3D0.0250 (6)0.0276 (6)0.0445 (7)0.0016 (5)0.0075 (5)0.0118 (5)
O4D0.0878 (13)0.0257 (7)0.1225 (16)0.0057 (8)0.0709 (12)0.0080 (8)
O5D0.038 (2)0.045 (2)0.141 (16)0.0225 (16)0.015 (4)0.031 (5)
O5DA0.045 (2)0.035 (2)0.075 (7)0.0157 (16)0.025 (3)0.008 (3)
O6D0.0262 (6)0.0556 (8)0.0445 (8)0.0018 (6)0.0111 (5)0.0065 (6)
O7D0.0333 (7)0.0399 (7)0.0446 (7)0.0085 (5)0.0031 (5)0.0130 (6)
N1D0.0243 (7)0.0248 (7)0.0523 (9)0.0015 (5)0.0087 (6)0.0080 (6)
N2D0.0384 (9)0.0290 (8)0.0369 (8)0.0069 (6)0.0062 (7)0.0043 (6)
N3D0.0245 (7)0.0423 (9)0.0260 (7)0.0038 (6)0.0007 (5)0.0049 (6)
C1D0.0253 (8)0.0242 (8)0.0280 (8)0.0015 (6)0.0001 (6)0.0052 (6)
C2D0.0211 (7)0.0244 (8)0.0283 (8)0.0016 (6)0.0015 (6)0.0022 (6)
C3D0.0211 (7)0.0251 (8)0.0246 (8)0.0003 (6)0.0004 (6)0.0040 (6)
C4D0.0271 (8)0.0264 (8)0.0238 (8)0.0030 (6)0.0000 (6)0.0025 (6)
C5D0.0220 (8)0.0343 (9)0.0252 (8)0.0041 (6)0.0025 (6)0.0005 (6)
C6D0.0227 (8)0.0334 (9)0.0237 (8)0.0028 (6)0.0020 (6)0.0027 (6)
O1E0.0381 (8)0.0269 (7)0.0914 (12)0.0065 (5)0.0036 (7)0.0034 (7)
O2E0.0224 (6)0.0378 (7)0.0552 (8)0.0012 (5)0.0018 (5)0.0052 (6)
O3E0.0225 (6)0.0262 (6)0.0341 (6)0.0002 (4)0.0068 (5)0.0058 (5)
O4E0.0464 (8)0.0228 (6)0.0692 (10)0.0008 (6)0.0221 (7)0.0001 (6)
O5E0.0317 (7)0.0446 (8)0.0922 (12)0.0163 (6)0.0089 (7)0.0199 (8)
O6E0.0254 (7)0.0687 (9)0.0358 (7)0.0100 (6)0.0100 (5)0.0017 (6)
O7E0.0402 (7)0.0501 (8)0.0457 (8)0.0185 (6)0.0040 (6)0.0210 (7)
N1E0.0236 (7)0.0273 (7)0.0315 (7)0.0001 (5)0.0020 (5)0.0073 (6)
N2E0.0322 (8)0.0280 (7)0.0449 (9)0.0089 (6)0.0164 (7)0.0009 (6)
N3E0.0282 (8)0.0489 (9)0.0234 (7)0.0141 (6)0.0014 (6)0.0073 (6)
C1E0.0277 (8)0.0277 (8)0.0222 (8)0.0055 (6)0.0019 (6)0.0045 (6)
C2E0.0203 (7)0.0263 (8)0.0240 (7)0.0010 (6)0.0003 (6)0.0008 (6)
C3E0.0219 (7)0.0227 (7)0.0219 (7)0.0018 (6)0.0022 (6)0.0019 (6)
C4E0.0247 (8)0.0240 (8)0.0266 (8)0.0001 (6)0.0060 (6)0.0009 (6)
C5E0.0208 (7)0.0341 (9)0.0251 (8)0.0004 (6)0.0051 (6)0.0037 (6)
C6E0.0239 (8)0.0365 (9)0.0206 (7)0.0096 (6)0.0017 (6)0.0015 (6)
N4A0.0278 (7)0.0204 (7)0.0421 (8)0.0044 (5)0.0006 (6)0.0008 (6)
N5A0.0233 (6)0.0186 (6)0.0311 (7)0.0019 (5)0.0003 (5)0.0001 (5)
N6A0.0192 (7)0.0209 (7)0.0364 (8)0.0005 (5)0.0060 (6)0.0041 (6)
C7A0.0299 (9)0.0250 (8)0.0333 (9)0.0003 (6)0.0009 (7)0.0036 (7)
C8A0.0236 (8)0.0211 (8)0.0384 (9)0.0033 (6)0.0039 (7)0.0018 (6)
C9A0.0251 (8)0.0263 (8)0.0325 (9)0.0042 (6)0.0041 (6)0.0012 (7)
C10A0.0293 (8)0.0214 (8)0.0337 (9)0.0026 (6)0.0021 (7)0.0042 (6)
C11A0.0240 (8)0.0193 (7)0.0382 (9)0.0031 (6)0.0035 (7)0.0011 (6)
C12A0.0243 (8)0.0225 (8)0.0372 (9)0.0026 (6)0.0080 (7)0.0010 (7)
N4B0.0290 (7)0.0199 (7)0.0516 (9)0.0043 (5)0.0009 (6)0.0004 (6)
N5B0.0234 (7)0.0219 (6)0.0294 (7)0.0031 (5)0.0003 (5)0.0008 (5)
N6B0.0204 (7)0.0190 (6)0.0347 (8)0.0027 (5)0.0064 (6)0.0037 (5)
C7B0.0298 (9)0.0260 (8)0.0352 (9)0.0004 (6)0.0003 (7)0.0016 (7)
C8B0.0253 (8)0.0244 (8)0.0435 (10)0.0037 (6)0.0058 (7)0.0037 (7)
C9B0.0238 (8)0.0267 (8)0.0338 (9)0.0033 (6)0.0027 (6)0.0003 (7)
C10B0.0299 (8)0.0268 (8)0.0294 (8)0.0037 (6)0.0009 (6)0.0042 (7)
C11B0.0252 (8)0.0204 (7)0.0343 (9)0.0044 (6)0.0048 (6)0.0029 (6)
C12B0.0248 (8)0.0238 (8)0.0329 (8)0.0039 (6)0.0078 (6)0.0002 (6)
N4C0.0319 (8)0.0211 (7)0.0462 (9)0.0051 (6)0.0016 (6)0.0013 (6)
N5C0.0248 (7)0.0193 (6)0.0353 (7)0.0032 (5)0.0013 (5)0.0022 (5)
N6C0.0186 (7)0.0226 (7)0.0304 (7)0.0003 (5)0.0034 (5)0.0042 (5)
C7C0.0349 (9)0.0269 (8)0.0358 (9)0.0014 (7)0.0013 (7)0.0009 (7)
C8C0.0284 (8)0.0283 (8)0.0363 (9)0.0061 (7)0.0026 (7)0.0032 (7)
C9C0.0264 (8)0.0210 (8)0.0433 (10)0.0021 (6)0.0020 (7)0.0036 (7)
C10C0.0299 (8)0.0232 (8)0.0358 (9)0.0019 (6)0.0047 (7)0.0017 (7)
C11C0.0226 (8)0.0206 (8)0.0399 (9)0.0035 (6)0.0002 (7)0.0001 (7)
C12C0.0248 (8)0.0250 (8)0.0325 (8)0.0034 (6)0.0047 (6)0.0012 (6)
N4D0.0304 (7)0.0217 (7)0.0421 (8)0.0027 (5)0.0029 (6)0.0012 (6)
N5D0.0236 (7)0.0222 (7)0.0309 (7)0.0034 (5)0.0024 (5)0.0023 (5)
N6D0.0218 (7)0.0198 (7)0.0290 (7)0.0016 (5)0.0049 (5)0.0026 (5)
C7D0.0245 (8)0.0292 (8)0.0355 (9)0.0028 (6)0.0018 (7)0.0033 (7)
C8D0.0231 (8)0.0232 (8)0.0369 (9)0.0029 (6)0.0020 (6)0.0048 (7)
C9D0.0315 (9)0.0294 (9)0.0342 (9)0.0021 (7)0.0017 (7)0.0004 (7)
C10D0.0286 (8)0.0279 (8)0.0294 (8)0.0044 (6)0.0036 (6)0.0012 (7)
C11D0.0258 (8)0.0236 (8)0.0316 (8)0.0056 (6)0.0009 (6)0.0014 (6)
C12D0.0258 (8)0.0275 (8)0.0317 (8)0.0036 (6)0.0051 (6)0.0048 (7)
N4E0.0329 (8)0.0224 (7)0.0462 (9)0.0037 (6)0.0022 (6)0.0007 (6)
N5E0.0263 (7)0.0217 (6)0.0307 (7)0.0037 (5)0.0018 (5)0.0007 (5)
N6E0.0218 (7)0.0200 (7)0.0319 (8)0.0015 (5)0.0056 (6)0.0022 (5)
C7E0.0328 (9)0.0277 (8)0.0395 (10)0.0000 (7)0.0014 (7)0.0027 (7)
C8E0.0286 (9)0.0238 (8)0.0400 (10)0.0042 (6)0.0027 (7)0.0040 (7)
C9E0.0251 (8)0.0305 (9)0.0386 (9)0.0033 (7)0.0025 (7)0.0006 (7)
C10E0.0345 (9)0.0277 (8)0.0295 (9)0.0030 (7)0.0049 (7)0.0038 (7)
C11E0.0286 (9)0.0232 (8)0.0346 (9)0.0043 (6)0.0008 (7)0.0027 (7)
C12E0.0280 (8)0.0273 (8)0.0307 (9)0.0032 (6)0.0056 (7)0.0030 (7)
Geometric parameters (Å, º) top
O1A—N1A1.227 (2)N6A—H6AC0.95 (2)
O2A—N1A1.224 (2)N6A—C12A1.485 (2)
O3A—C3A1.2448 (18)C7A—H7A0.9500
O4A—N2A1.2268 (19)C7A—C9A1.359 (2)
O5A—N2A1.2139 (19)C8A—H8A0.9500
O6A—N3A1.2322 (19)C9A—H9A0.9500
O7A—N3A1.223 (2)C10A—H10A0.9900
N1A—C2A1.459 (2)C10A—H10B0.9900
N2A—C4A1.449 (2)C10A—C11A1.525 (2)
N3A—C6A1.449 (2)C11A—H11A0.9900
C1A—H1A0.9500C11A—H11B0.9900
C1A—C2A1.373 (2)C11A—C12A1.521 (2)
C1A—C6A1.396 (2)C12A—H12A0.9900
C2A—C3A1.452 (2)C12A—H12B0.9900
C3A—C4A1.453 (2)N4B—C7B1.367 (2)
C4A—C5A1.376 (2)N4B—C8B1.316 (2)
C5A—H5A0.9500N5B—C8B1.348 (2)
C5A—C6A1.376 (2)N5B—C9B1.371 (2)
O1B—N3B1.2231 (17)N5B—C10B1.462 (2)
O2B—N3B1.2270 (17)N6B—H6BA0.92 (2)
O3B—C5B1.2451 (18)N6B—H6BB0.89 (2)
O4B—N2B1.225 (2)N6B—H6BC0.92 (2)
O5B—N2B1.2291 (19)N6B—C12B1.487 (2)
O6B—N1B1.2295 (19)C7B—H7B0.9500
O7B—N1B1.2298 (19)C7B—C9B1.355 (2)
N1B—C2B1.447 (2)C8B—H8B0.9500
N2B—C4B1.453 (2)C9B—H9B0.9500
N3B—C6B1.4567 (18)C10B—H10C0.9900
C1B—H1B0.9500C10B—H10D0.9900
C1B—C2B1.391 (2)C10B—C11B1.526 (2)
C1B—C6B1.371 (2)C11B—H11C0.9900
C2B—C3B1.380 (2)C11B—H11D0.9900
C3B—H3B0.9500C11B—C12B1.520 (2)
C3B—C4B1.371 (2)C12B—H12C0.9900
C4B—C5B1.452 (2)C12B—H12D0.9900
C5B—C6B1.451 (2)N4C—C7C1.375 (2)
O1C—N1C1.2267 (18)N4C—C9C1.315 (2)
O2C—N1C1.2206 (19)N5C—C8C1.372 (2)
O3C—C3C1.2492 (18)N5C—C9C1.348 (2)
O4C—N2C1.2238 (18)N5C—C10C1.461 (2)
O5C—N2C1.235 (2)N6C—H6CA0.85 (2)
O6C—N3C1.2329 (18)N6C—H6CB0.89 (2)
O7C—N3C1.2273 (19)N6C—H6CC0.92 (2)
N1C—C2C1.4523 (19)N6C—C12C1.484 (2)
N2C—C4C1.446 (2)C7C—H7C0.9500
N3C—C6C1.4474 (19)C7C—C8C1.356 (2)
C1C—H1C0.9500C8C—H8C0.9500
C1C—C2C1.377 (2)C9C—H9C0.9500
C1C—C6C1.387 (2)C10C—H10E0.9900
C2C—C3C1.448 (2)C10C—H10F0.9900
C3C—C4C1.450 (2)C10C—C11C1.525 (2)
C4C—C5C1.375 (2)C11C—H11E0.9900
C5C—H5C0.9500C11C—H11F0.9900
C5C—C6C1.372 (2)C11C—C12C1.520 (2)
O1D—N1D1.201 (2)C12C—H12E0.9900
O2D—N1D1.229 (2)C12C—H12F0.9900
O3D—C3D1.2469 (18)N4D—C8D1.315 (2)
O4D—N2D1.198 (2)N4D—C9D1.373 (2)
O5D—N2D1.172 (6)N5D—C7D1.373 (2)
O5DA—N2D1.284 (6)N5D—C8D1.3493 (19)
O6D—N3D1.2288 (19)N5D—C10D1.465 (2)
O7D—N3D1.2276 (19)N6D—H6DA0.89 (2)
N1D—C2D1.457 (2)N6D—H6DB0.89 (2)
N2D—C4D1.451 (2)N6D—H6DC0.89 (2)
N3D—C6D1.452 (2)N6D—C12D1.482 (2)
C1D—H1D0.9500C7D—H7D0.9500
C1D—C2D1.372 (2)C7D—C9D1.353 (2)
C1D—C6D1.395 (2)C8D—H8D0.9500
C2D—C3D1.450 (2)C9D—H9D0.9500
C3D—C4D1.456 (2)C10D—H10G0.9900
C4D—C5D1.378 (2)C10D—H10H0.9900
C5D—H5D0.9500C10D—C11D1.524 (2)
C5D—C6D1.374 (2)C11D—H11G0.9900
O1E—N1E1.2253 (18)C11D—H11H0.9900
O2E—N1E1.2249 (18)C11D—C12D1.517 (2)
O3E—C3E1.2472 (18)C12D—H12G0.9900
O4E—N2E1.2234 (19)C12D—H12H0.9900
O5E—N2E1.233 (2)N4E—C7E1.369 (2)
O6E—N3E1.228 (2)N4E—C8E1.317 (2)
O7E—N3E1.232 (2)N5E—C8E1.347 (2)
N1E—C2E1.4546 (19)N5E—C9E1.372 (2)
N2E—C4E1.448 (2)N5E—C10E1.464 (2)
N3E—C6E1.448 (2)N6E—H6EA0.91 (2)
C1E—H1E0.9500N6E—H6EB0.87 (2)
C1E—C2E1.373 (2)N6E—H6EC0.93 (2)
C1E—C6E1.385 (2)N6E—C12E1.483 (2)
C2E—C3E1.452 (2)C7E—H7E0.9500
C3E—C4E1.453 (2)C7E—C9E1.353 (2)
C4E—C5E1.370 (2)C8E—H8E0.9500
C5E—H5E0.9500C9E—H9E0.9500
C5E—C6E1.380 (2)C10E—H10I0.9900
N4A—C7A1.372 (2)C10E—H10J0.9900
N4A—C8A1.316 (2)C10E—C11E1.526 (2)
N5A—C8A1.3485 (19)C11E—H11I0.9900
N5A—C9A1.374 (2)C11E—H11J0.9900
N5A—C10A1.4645 (19)C11E—C12E1.517 (2)
N6A—H6AA0.85 (2)C12E—H12I0.9900
N6A—H6AB0.91 (2)C12E—H12J0.9900
O1A—N1A—C2A117.71 (14)C11A—C10A—H10B109.2
O2A—N1A—O1A123.60 (15)C10A—C11A—H11A109.3
O2A—N1A—C2A118.68 (14)C10A—C11A—H11B109.3
O4A—N2A—C4A119.55 (14)H11A—C11A—H11B107.9
O5A—N2A—O4A121.60 (15)C12A—C11A—C10A111.75 (13)
O5A—N2A—C4A118.85 (15)C12A—C11A—H11A109.3
O6A—N3A—C6A117.84 (15)C12A—C11A—H11B109.3
O7A—N3A—O6A123.80 (14)N6A—C12A—C11A111.71 (13)
O7A—N3A—C6A118.35 (14)N6A—C12A—H12A109.3
C2A—C1A—H1A120.6N6A—C12A—H12B109.3
C2A—C1A—C6A118.77 (15)C11A—C12A—H12A109.3
C6A—C1A—H1A120.6C11A—C12A—H12B109.3
C1A—C2A—N1A116.22 (14)H12A—C12A—H12B107.9
C1A—C2A—C3A124.90 (14)C8B—N4B—C7B105.42 (14)
C3A—C2A—N1A118.87 (13)C8B—N5B—C9B106.63 (13)
O3A—C3A—C2A124.92 (14)C8B—N5B—C10B127.79 (14)
O3A—C3A—C4A124.07 (14)C9B—N5B—C10B125.57 (13)
C2A—C3A—C4A111.01 (13)H6BA—N6B—H6BB110.2 (17)
N2A—C4A—C3A119.08 (14)H6BA—N6B—H6BC108.0 (16)
C5A—C4A—N2A116.44 (14)H6BB—N6B—H6BC108.1 (17)
C5A—C4A—C3A124.48 (14)C12B—N6B—H6BA111.4 (11)
C4A—C5A—H5A120.3C12B—N6B—H6BB108.3 (13)
C6A—C5A—C4A119.37 (14)C12B—N6B—H6BC110.8 (12)
C6A—C5A—H5A120.3N4B—C7B—H7B125.0
C1A—C6A—N3A118.97 (15)C9B—C7B—N4B110.00 (15)
C5A—C6A—N3A120.01 (14)C9B—C7B—H7B125.0
C5A—C6A—C1A121.00 (14)N4B—C8B—N5B111.75 (15)
O6B—N1B—O7B123.70 (14)N4B—C8B—H8B124.1
O6B—N1B—C2B118.19 (14)N5B—C8B—H8B124.1
O7B—N1B—C2B118.11 (14)N5B—C9B—H9B126.9
O4B—N2B—O5B123.03 (15)C7B—C9B—N5B106.18 (14)
O4B—N2B—C4B119.13 (14)C7B—C9B—H9B126.9
O5B—N2B—C4B117.83 (15)N5B—C10B—H10C109.2
O1B—N3B—O2B123.41 (13)N5B—C10B—H10D109.2
O1B—N3B—C6B118.79 (13)N5B—C10B—C11B112.23 (13)
O2B—N3B—C6B117.72 (13)H10C—C10B—H10D107.9
C2B—C1B—H1B120.6C11B—C10B—H10C109.2
C6B—C1B—H1B120.6C11B—C10B—H10D109.2
C6B—C1B—C2B118.72 (14)C10B—C11B—H11C109.3
C1B—C2B—N1B120.21 (15)C10B—C11B—H11D109.3
C3B—C2B—N1B118.68 (14)H11C—C11B—H11D107.9
C3B—C2B—C1B121.07 (14)C12B—C11B—C10B111.74 (13)
C2B—C3B—H3B120.3C12B—C11B—H11C109.3
C4B—C3B—C2B119.38 (14)C12B—C11B—H11D109.3
C4B—C3B—H3B120.3N6B—C12B—C11B112.16 (13)
C3B—C4B—N2B115.98 (14)N6B—C12B—H12C109.2
C3B—C4B—C5B124.57 (14)N6B—C12B—H12D109.2
C5B—C4B—N2B119.45 (14)C11B—C12B—H12C109.2
O3B—C5B—C4B124.26 (14)C11B—C12B—H12D109.2
O3B—C5B—C6B124.58 (13)H12C—C12B—H12D107.9
C6B—C5B—C4B110.99 (13)C9C—N4C—C7C105.23 (14)
C1B—C6B—N3B116.43 (13)C8C—N5C—C10C126.59 (14)
C1B—C6B—C5B125.00 (14)C9C—N5C—C8C106.65 (14)
C5B—C6B—N3B118.57 (13)C9C—N5C—C10C126.75 (15)
O1C—N1C—C2C118.16 (14)H6CA—N6C—H6CB109.2 (17)
O2C—N1C—O1C123.32 (14)H6CA—N6C—H6CC109.4 (17)
O2C—N1C—C2C118.50 (14)H6CB—N6C—H6CC106.2 (16)
O4C—N2C—O5C123.11 (14)C12C—N6C—H6CA109.0 (12)
O4C—N2C—C4C119.00 (14)C12C—N6C—H6CB111.9 (12)
O5C—N2C—C4C117.88 (14)C12C—N6C—H6CC111.1 (12)
O6C—N3C—C6C117.94 (14)N4C—C7C—H7C125.1
O7C—N3C—O6C123.59 (13)C8C—C7C—N4C109.87 (16)
O7C—N3C—C6C118.46 (14)C8C—C7C—H7C125.1
C2C—C1C—H1C120.6N5C—C8C—H8C126.9
C2C—C1C—C6C118.77 (14)C7C—C8C—N5C106.29 (15)
C6C—C1C—H1C120.6C7C—C8C—H8C126.9
C1C—C2C—N1C115.76 (13)N4C—C9C—N5C111.97 (15)
C1C—C2C—C3C125.07 (14)N4C—C9C—H9C124.0
C3C—C2C—N1C119.16 (13)N5C—C9C—H9C124.0
O3C—C3C—C2C125.04 (14)N5C—C10C—H10E109.1
O3C—C3C—C4C124.28 (14)N5C—C10C—H10F109.1
C2C—C3C—C4C110.67 (13)N5C—C10C—C11C112.30 (14)
N2C—C4C—C3C119.42 (13)H10E—C10C—H10F107.9
C5C—C4C—N2C115.46 (14)C11C—C10C—H10E109.1
C5C—C4C—C3C125.02 (14)C11C—C10C—H10F109.1
C4C—C5C—H5C120.4C10C—C11C—H11E109.3
C6C—C5C—C4C119.16 (14)C10C—C11C—H11F109.3
C6C—C5C—H5C120.4H11E—C11C—H11F108.0
C1C—C6C—N3C119.58 (14)C12C—C11C—C10C111.63 (13)
C5C—C6C—N3C119.24 (14)C12C—C11C—H11E109.3
C5C—C6C—C1C121.18 (14)C12C—C11C—H11F109.3
O1D—N1D—O2D123.01 (16)N6C—C12C—C11C111.62 (13)
O1D—N1D—C2D118.78 (15)N6C—C12C—H12E109.3
O2D—N1D—C2D118.13 (14)N6C—C12C—H12F109.3
O4D—N2D—O5DA121.1 (4)C11C—C12C—H12E109.3
O4D—N2D—C4D121.11 (15)C11C—C12C—H12F109.3
O5D—N2D—O4D116.2 (6)H12E—C12C—H12F108.0
O5D—N2D—C4D120.7 (4)C8D—N4D—C9D105.07 (14)
O5DA—N2D—C4D114.8 (6)C7D—N5D—C10D126.36 (13)
O6D—N3D—C6D117.99 (15)C8D—N5D—C7D106.60 (14)
O7D—N3D—O6D123.75 (14)C8D—N5D—C10D126.98 (14)
O7D—N3D—C6D118.26 (14)H6DA—N6D—H6DB110.1 (17)
C2D—C1D—H1D120.7H6DA—N6D—H6DC106.3 (16)
C2D—C1D—C6D118.59 (15)H6DB—N6D—H6DC109.1 (17)
C6D—C1D—H1D120.7C12D—N6D—H6DA110.3 (12)
C1D—C2D—N1D116.12 (14)C12D—N6D—H6DB109.7 (13)
C1D—C2D—C3D125.24 (14)C12D—N6D—H6DC111.3 (12)
C3D—C2D—N1D118.64 (13)N5D—C7D—H7D127.0
O3D—C3D—C2D123.99 (14)C9D—C7D—N5D106.10 (14)
O3D—C3D—C4D124.81 (14)C9D—C7D—H7D127.0
C2D—C3D—C4D111.19 (13)N4D—C8D—N5D111.99 (15)
N2D—C4D—C3D120.05 (14)N4D—C8D—H8D124.0
C5D—C4D—N2D116.02 (14)N5D—C8D—H8D124.0
C5D—C4D—C3D123.92 (15)N4D—C9D—H9D124.9
C4D—C5D—H5D120.0C7D—C9D—N4D110.24 (15)
C6D—C5D—C4D119.94 (15)C7D—C9D—H9D124.9
C6D—C5D—H5D120.0N5D—C10D—H10G109.2
C1D—C6D—N3D119.68 (15)N5D—C10D—H10H109.2
C5D—C6D—N3D119.38 (14)N5D—C10D—C11D112.06 (13)
C5D—C6D—C1D120.93 (15)H10G—C10D—H10H107.9
O1E—N1E—C2E118.81 (13)C11D—C10D—H10G109.2
O2E—N1E—O1E123.10 (14)C11D—C10D—H10H109.2
O2E—N1E—C2E118.02 (13)C10D—C11D—H11G109.3
O4E—N2E—O5E122.89 (15)C10D—C11D—H11H109.3
O4E—N2E—C4E119.37 (15)H11G—C11D—H11H108.0
O5E—N2E—C4E117.74 (15)C12D—C11D—C10D111.64 (13)
O6E—N3E—O7E123.84 (15)C12D—C11D—H11G109.3
O6E—N3E—C6E118.14 (15)C12D—C11D—H11H109.3
O7E—N3E—C6E118.01 (15)N6D—C12D—C11D113.07 (13)
C2E—C1E—H1E120.6N6D—C12D—H12G109.0
C2E—C1E—C6E118.78 (15)N6D—C12D—H12H109.0
C6E—C1E—H1E120.6C11D—C12D—H12G109.0
C1E—C2E—N1E116.32 (14)C11D—C12D—H12H109.0
C1E—C2E—C3E124.94 (14)H12G—C12D—H12H107.8
C3E—C2E—N1E118.74 (13)C8E—N4E—C7E105.39 (14)
O3E—C3E—C2E124.73 (14)C8E—N5E—C9E106.80 (14)
O3E—C3E—C4E124.29 (14)C8E—N5E—C10E127.40 (15)
C2E—C3E—C4E110.81 (13)C9E—N5E—C10E125.74 (14)
N2E—C4E—C3E119.12 (13)H6EA—N6E—H6EB109.0 (18)
C5E—C4E—N2E115.91 (14)H6EA—N6E—H6EC105.3 (17)
C5E—C4E—C3E124.92 (15)H6EB—N6E—H6EC110.5 (17)
C4E—C5E—H5E120.5C12E—N6E—H6EA111.4 (13)
C4E—C5E—C6E119.08 (15)C12E—N6E—H6EB109.5 (13)
C6E—C5E—H5E120.5C12E—N6E—H6EC111.0 (13)
C1E—C6E—N3E120.04 (15)N4E—C7E—H7E124.9
C5E—C6E—N3E118.65 (15)C9E—C7E—N4E110.10 (16)
C5E—C6E—C1E121.31 (14)C9E—C7E—H7E124.9
C8A—N4A—C7A105.28 (13)N4E—C8E—N5E111.62 (15)
C8A—N5A—C9A106.91 (13)N4E—C8E—H8E124.2
C8A—N5A—C10A126.75 (14)N5E—C8E—H8E124.2
C9A—N5A—C10A126.32 (13)N5E—C9E—H9E127.0
H6AA—N6A—H6AB110.8 (17)C7E—C9E—N5E106.09 (15)
H6AA—N6A—H6AC109.0 (17)C7E—C9E—H9E127.0
H6AB—N6A—H6AC108.3 (16)N5E—C10E—H10I109.2
C12A—N6A—H6AA108.4 (13)N5E—C10E—H10J109.2
C12A—N6A—H6AB110.0 (12)N5E—C10E—C11E112.11 (13)
C12A—N6A—H6AC110.3 (12)H10I—C10E—H10J107.9
N4A—C7A—H7A124.9C11E—C10E—H10I109.2
C9A—C7A—N4A110.19 (15)C11E—C10E—H10J109.2
C9A—C7A—H7A124.9C10E—C11E—H11I109.3
N4A—C8A—N5A111.82 (14)C10E—C11E—H11J109.3
N4A—C8A—H8A124.1H11I—C11E—H11J108.0
N5A—C8A—H8A124.1C12E—C11E—C10E111.61 (13)
N5A—C9A—H9A127.1C12E—C11E—H11I109.3
C7A—C9A—N5A105.80 (14)C12E—C11E—H11J109.3
C7A—C9A—H9A127.1N6E—C12E—C11E112.69 (13)
N5A—C10A—H10A109.2N6E—C12E—H12I109.1
N5A—C10A—H10B109.2N6E—C12E—H12J109.1
N5A—C10A—C11A112.22 (13)C11E—C12E—H12I109.1
H10A—C10A—H10B107.9C11E—C12E—H12J109.1
C11A—C10A—H10A109.2H12I—C12E—H12J107.8
O1A—N1A—C2A—C1A35.4 (2)O7D—N3D—C6D—C5D179.93 (15)
O1A—N1A—C2A—C3A143.82 (17)N1D—C2D—C3D—O3D0.7 (2)
O2A—N1A—C2A—C1A144.20 (17)N1D—C2D—C3D—C4D178.26 (14)
O2A—N1A—C2A—C3A36.5 (2)N2D—C4D—C5D—C6D174.80 (15)
O3A—C3A—C4A—N2A7.5 (2)C1D—C2D—C3D—O3D179.78 (16)
O3A—C3A—C4A—C5A172.60 (15)C1D—C2D—C3D—C4D1.3 (2)
O4A—N2A—C4A—C3A26.1 (2)C2D—C1D—C6D—N3D176.99 (14)
O4A—N2A—C4A—C5A153.79 (16)C2D—C1D—C6D—C5D3.4 (2)
O5A—N2A—C4A—C3A154.60 (17)C2D—C3D—C4D—N2D174.13 (14)
O5A—N2A—C4A—C5A25.5 (2)C2D—C3D—C4D—C5D4.4 (2)
O6A—N3A—C6A—C1A179.68 (14)C3D—C4D—C5D—C6D3.8 (2)
O6A—N3A—C6A—C5A1.3 (2)C4D—C5D—C6D—N3D179.98 (14)
O7A—N3A—C6A—C1A0.9 (2)C4D—C5D—C6D—C1D0.4 (2)
O7A—N3A—C6A—C5A179.23 (15)C6D—C1D—C2D—N1D178.02 (14)
N1A—C2A—C3A—O3A4.7 (2)C6D—C1D—C2D—C3D2.4 (3)
N1A—C2A—C3A—C4A174.90 (14)O1E—N1E—C2E—C1E33.6 (2)
N2A—C4A—C5A—C6A174.32 (14)O1E—N1E—C2E—C3E145.62 (16)
C1A—C2A—C3A—O3A176.05 (16)O2E—N1E—C2E—C1E143.49 (15)
C1A—C2A—C3A—C4A4.3 (2)O2E—N1E—C2E—C3E37.3 (2)
C2A—C1A—C6A—N3A177.65 (14)O3E—C3E—C4E—N2E5.2 (2)
C2A—C1A—C6A—C5A4.0 (2)O3E—C3E—C4E—C5E171.92 (15)
C2A—C3A—C4A—N2A172.17 (14)O4E—N2E—C4E—C3E34.7 (2)
C2A—C3A—C4A—C5A7.7 (2)O4E—N2E—C4E—C5E147.92 (16)
C3A—C4A—C5A—C6A5.6 (2)O5E—N2E—C4E—C3E144.93 (16)
C4A—C5A—C6A—N3A179.10 (14)O5E—N2E—C4E—C5E32.4 (2)
C4A—C5A—C6A—C1A0.8 (2)O6E—N3E—C6E—C1E172.73 (14)
C6A—C1A—C2A—N1A179.61 (14)O6E—N3E—C6E—C5E6.7 (2)
C6A—C1A—C2A—C3A1.2 (2)O7E—N3E—C6E—C1E8.1 (2)
O1B—N3B—C6B—C1B33.8 (2)O7E—N3E—C6E—C5E172.40 (15)
O1B—N3B—C6B—C5B145.57 (15)N1E—C2E—C3E—O3E8.5 (2)
O2B—N3B—C6B—C1B143.09 (15)N1E—C2E—C3E—C4E176.08 (13)
O2B—N3B—C6B—C5B37.5 (2)N2E—C4E—C5E—C6E179.10 (14)
O3B—C5B—C6B—N3B9.6 (2)C1E—C2E—C3E—O3E170.70 (15)
O3B—C5B—C6B—C1B169.72 (15)C1E—C2E—C3E—C4E4.8 (2)
O4B—N2B—C4B—C3B150.42 (15)C2E—C1E—C6E—N3E177.47 (14)
O4B—N2B—C4B—C5B29.8 (2)C2E—C1E—C6E—C5E2.0 (2)
O5B—N2B—C4B—C3B28.9 (2)C2E—C3E—C4E—N2E179.32 (14)
O5B—N2B—C4B—C5B150.98 (15)C2E—C3E—C4E—C5E3.6 (2)
O6B—N1B—C2B—C1B175.70 (14)C3E—C4E—C5E—C6E1.9 (2)
O6B—N1B—C2B—C3B1.8 (2)C4E—C5E—C6E—N3E178.58 (14)
O7B—N1B—C2B—C1B4.4 (2)C4E—C5E—C6E—C1E0.9 (2)
O7B—N1B—C2B—C3B178.12 (14)C6E—C1E—C2E—N1E176.60 (14)
N1B—C2B—C3B—C4B176.94 (14)C6E—C1E—C2E—C3E4.2 (2)
N2B—C4B—C5B—O3B10.0 (2)N4A—C7A—C9A—N5A0.25 (19)
N2B—C4B—C5B—C6B174.48 (14)N5A—C10A—C11A—C12A75.73 (17)
C1B—C2B—C3B—C4B0.5 (2)C7A—N4A—C8A—N5A0.13 (19)
C2B—C1B—C6B—N3B177.07 (13)C8A—N4A—C7A—C9A0.24 (19)
C2B—C1B—C6B—C5B3.6 (2)C8A—N5A—C9A—C7A0.17 (18)
C2B—C3B—C4B—N2B176.73 (14)C8A—N5A—C10A—C11A99.79 (18)
C2B—C3B—C4B—C5B3.5 (2)C9A—N5A—C8A—N4A0.02 (19)
C3B—C4B—C5B—O3B169.83 (15)C9A—N5A—C10A—C11A81.85 (19)
C3B—C4B—C5B—C6B5.7 (2)C10A—N5A—C8A—N4A178.60 (14)
C4B—C5B—C6B—N3B174.87 (13)C10A—N5A—C9A—C7A178.46 (15)
C4B—C5B—C6B—C1B5.8 (2)C10A—C11A—C12A—N6A169.81 (13)
C6B—C1B—C2B—N1B176.85 (13)N4B—C7B—C9B—N5B0.42 (19)
C6B—C1B—C2B—C3B0.6 (2)N5B—C10B—C11B—C12B77.05 (17)
O1C—N1C—C2C—C1C35.9 (2)C7B—N4B—C8B—N5B0.2 (2)
O1C—N1C—C2C—C3C145.17 (15)C8B—N4B—C7B—C9B0.1 (2)
O2C—N1C—C2C—C1C142.27 (16)C8B—N5B—C9B—C7B0.53 (18)
O2C—N1C—C2C—C3C36.7 (2)C8B—N5B—C10B—C11B96.84 (19)
O3C—C3C—C4C—N2C0.5 (2)C9B—N5B—C8B—N4B0.48 (19)
O3C—C3C—C4C—C5C175.73 (15)C9B—N5B—C10B—C11B82.11 (19)
O4C—N2C—C4C—C3C36.2 (2)C10B—N5B—C8B—N4B179.59 (15)
O4C—N2C—C4C—C5C147.29 (15)C10B—N5B—C9B—C7B179.66 (14)
O5C—N2C—C4C—C3C143.12 (16)C10B—C11B—C12B—N6B167.69 (13)
O5C—N2C—C4C—C5C33.4 (2)N4C—C7C—C8C—N5C0.2 (2)
O6C—N3C—C6C—C1C174.06 (14)N5C—C10C—C11C—C12C74.86 (18)
O6C—N3C—C6C—C5C5.9 (2)C7C—N4C—C9C—N5C0.14 (19)
O7C—N3C—C6C—C1C7.1 (2)C8C—N5C—C9C—N4C0.01 (19)
O7C—N3C—C6C—C5C172.89 (15)C8C—N5C—C10C—C11C79.6 (2)
N1C—C2C—C3C—O3C0.4 (2)C9C—N4C—C7C—C8C0.2 (2)
N1C—C2C—C3C—C4C179.80 (13)C9C—N5C—C8C—C7C0.12 (19)
N2C—C4C—C5C—C6C179.99 (14)C9C—N5C—C10C—C11C101.93 (19)
C1C—C2C—C3C—O3C178.42 (15)C10C—N5C—C8C—C7C178.57 (15)
C1C—C2C—C3C—C4C1.0 (2)C10C—N5C—C9C—N4C178.70 (15)
C2C—C1C—C6C—N3C178.18 (14)C10C—C11C—C12C—N6C166.96 (13)
C2C—C1C—C6C—C5C1.8 (2)N5D—C7D—C9D—N4D0.43 (19)
C2C—C3C—C4C—N2C179.86 (14)N5D—C10D—C11D—C12D70.02 (18)
C2C—C3C—C4C—C5C3.7 (2)C7D—N5D—C8D—N4D0.51 (19)
C3C—C4C—C5C—C6C3.7 (2)C7D—N5D—C10D—C11D77.33 (19)
C4C—C5C—C6C—N3C179.33 (14)C8D—N4D—C9D—C7D0.13 (19)
C4C—C5C—C6C—C1C0.7 (2)C8D—N5D—C7D—C9D0.56 (18)
C6C—C1C—C2C—N1C177.26 (14)C8D—N5D—C10D—C11D99.47 (18)
C6C—C1C—C2C—C3C1.6 (2)C9D—N4D—C8D—N5D0.24 (19)
O1D—N1D—C2D—C1D34.2 (2)C10D—N5D—C7D—C9D177.90 (15)
O1D—N1D—C2D—C3D145.42 (19)C10D—N5D—C8D—N4D177.83 (14)
O2D—N1D—C2D—C1D142.63 (16)C10D—C11D—C12D—N6D162.89 (13)
O2D—N1D—C2D—C3D37.8 (2)N4E—C7E—C9E—N5E0.4 (2)
O3D—C3D—C4D—N2D4.8 (2)N5E—C10E—C11E—C12E73.02 (18)
O3D—C3D—C4D—C5D176.62 (16)C7E—N4E—C8E—N5E0.1 (2)
O4D—N2D—C4D—C3D5.9 (3)C8E—N4E—C7E—C9E0.2 (2)
O4D—N2D—C4D—C5D172.77 (19)C8E—N5E—C9E—C7E0.41 (19)
O5D—N2D—C4D—C3D158 (2)C8E—N5E—C10E—C11E95.96 (19)
O5D—N2D—C4D—C5D24 (2)C9E—N5E—C8E—N4E0.3 (2)
O5DA—N2D—C4D—C3D166.4 (11)C9E—N5E—C10E—C11E80.7 (2)
O5DA—N2D—C4D—C5D12.3 (11)C10E—N5E—C8E—N4E177.52 (15)
O6D—N3D—C6D—C1D179.42 (15)C10E—N5E—C9E—C7E177.67 (15)
O6D—N3D—C6D—C5D0.9 (2)C10E—C11E—C12E—N6E165.79 (14)
O7D—N3D—C6D—C1D0.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6A—H6AA···O3Ei0.85 (2)2.06 (2)2.8943 (18)167.5 (18)
N6A—H6AB···O3Dii0.91 (2)2.08 (2)2.8671 (18)143.1 (16)
N6A—H6AB···O4Dii0.91 (2)2.25 (2)2.961 (2)134.6 (15)
N6A—H6AC···N4C0.95 (2)1.87 (2)2.8157 (19)172.5 (18)
N6B—H6BA···O3Biii0.92 (2)2.117 (19)2.8728 (17)138.5 (15)
N6B—H6BA···O4Biii0.92 (2)2.268 (19)3.006 (2)136.6 (15)
N6B—H6BB···O3B0.89 (2)2.00 (2)2.8502 (17)161.0 (19)
N6B—H6BC···N4Aiv0.92 (2)1.88 (2)2.7988 (19)173.4 (17)
N6C—H6CA···O2Cv0.85 (2)2.305 (18)2.8334 (19)120.9 (15)
N6C—H6CA···O3Cv0.85 (2)2.10 (2)2.8944 (18)155.4 (17)
N6C—H6CB···O3Avi0.89 (2)2.174 (19)2.9145 (18)140.2 (16)
N6C—H6CB···O4Avi0.89 (2)2.270 (19)2.986 (2)137.3 (15)
N6C—H6CC···N4Dvi0.92 (2)1.91 (2)2.8179 (19)167.6 (17)
N6D—H6DA···O2Avii0.89 (2)2.361 (19)2.9631 (19)124.9 (15)
N6D—H6DA···O3Avii0.89 (2)2.06 (2)2.8340 (17)145.0 (16)
N6D—H6DB···O3Cvi0.89 (2)2.16 (2)2.9171 (17)142.0 (17)
N6D—H6DB···O4Cvi0.89 (2)2.27 (2)2.9323 (19)130.5 (16)
N6D—H6DC···N4E0.89 (2)1.91 (2)2.7932 (19)174.0 (17)
N6E—H6EA···O2Dviii0.91 (2)2.32 (2)2.973 (2)128.7 (17)
N6E—H6EA···O3Dviii0.91 (2)2.06 (2)2.8527 (18)145.4 (18)
N6E—H6EB···O3E0.87 (2)2.19 (2)2.9056 (18)139.6 (17)
N6E—H6EB···O4E0.87 (2)2.33 (2)3.010 (2)135.3 (16)
N6E—H6EC···N4Bviii0.93 (2)1.85 (2)2.7750 (19)174.0 (19)
C8A—H8A···O2Bix0.952.463.0887 (19)123
C9A—H9A···O5E0.952.433.243 (2)144
C12A—H12B···O7Aix0.992.463.313 (2)145
C9B—H9B···O5Bi0.952.373.224 (2)150
C12B—H12D···O7Cvi0.992.473.335 (2)145
C8C—H8C···O5Cvi0.952.333.194 (2)152
C9C—H9C···O2Ei0.952.493.105 (2)123
C7D—H7D···O5Avi0.952.353.233 (2)155
C11D—H11H···O6Avi0.992.553.421 (2)147
C12D—H12G···O6Bvii0.992.433.238 (2)139
C9E—H9E···O5Dii0.952.273.162 (6)156
C9E—H9E···O5DAii0.952.563.357 (17)141
C12E—H12I···O6Eviii0.992.343.186 (2)142
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+1, z; (iv) x+3/2, y+1/2, z+1/2; (v) x+2, y+1, z+1; (vi) x+1, y+1, z+1; (vii) x, y+1, z+1; (viii) x1/2, y+1/2, z+1/2; (ix) x+3/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6A—H6AA···O3Ei0.85 (2)2.06 (2)2.8943 (18)167.5 (18)
N6A—H6AB···O3Dii0.91 (2)2.08 (2)2.8671 (18)143.1 (16)
N6A—H6AB···O4Dii0.91 (2)2.25 (2)2.961 (2)134.6 (15)
N6A—H6AC···N4C0.95 (2)1.87 (2)2.8157 (19)172.5 (18)
N6B—H6BA···O3Biii0.92 (2)2.117 (19)2.8728 (17)138.5 (15)
N6B—H6BA···O4Biii0.92 (2)2.268 (19)3.006 (2)136.6 (15)
N6B—H6BB···O3B0.89 (2)2.00 (2)2.8502 (17)161.0 (19)
N6B—H6BC···N4Aiv0.92 (2)1.88 (2)2.7988 (19)173.4 (17)
N6C—H6CA···O2Cv0.85 (2)2.305 (18)2.8334 (19)120.9 (15)
N6C—H6CA···O3Cv0.85 (2)2.10 (2)2.8944 (18)155.4 (17)
N6C—H6CB···O3Avi0.89 (2)2.174 (19)2.9145 (18)140.2 (16)
N6C—H6CB···O4Avi0.89 (2)2.270 (19)2.986 (2)137.3 (15)
N6C—H6CC···N4Dvi0.92 (2)1.91 (2)2.8179 (19)167.6 (17)
N6D—H6DA···O2Avii0.89 (2)2.361 (19)2.9631 (19)124.9 (15)
N6D—H6DA···O3Avii0.89 (2)2.06 (2)2.8340 (17)145.0 (16)
N6D—H6DB···O3Cvi0.89 (2)2.16 (2)2.9171 (17)142.0 (17)
N6D—H6DB···O4Cvi0.89 (2)2.27 (2)2.9323 (19)130.5 (16)
N6D—H6DC···N4E0.89 (2)1.91 (2)2.7932 (19)174.0 (17)
N6E—H6EA···O2Dviii0.91 (2)2.32 (2)2.973 (2)128.7 (17)
N6E—H6EA···O3Dviii0.91 (2)2.06 (2)2.8527 (18)145.4 (18)
N6E—H6EB···O3E0.87 (2)2.19 (2)2.9056 (18)139.6 (17)
N6E—H6EB···O4E0.87 (2)2.33 (2)3.010 (2)135.3 (16)
N6E—H6EC···N4Bviii0.93 (2)1.85 (2)2.7750 (19)174.0 (19)
C8A—H8A···O2Bix0.952.463.0887 (19)123.2
C9A—H9A···O5E0.952.433.243 (2)143.5
C12A—H12B···O7Aix0.992.463.313 (2)144.7
C9B—H9B···O5Bi0.952.373.224 (2)149.7
C12B—H12D···O7Cvi0.992.473.335 (2)145.2
C8C—H8C···O5Cvi0.952.333.194 (2)151.7
C9C—H9C···O2Ei0.952.493.105 (2)122.5
C7D—H7D···O5Avi0.952.353.233 (2)154.5
C11D—H11H···O6Avi0.992.553.421 (2)147.1
C12D—H12G···O6Bvii0.992.433.238 (2)138.7
C9E—H9E···O5Dii0.952.273.162 (6)155.5
C9E—H9E···O5DAii0.952.563.357 (17)141.3
C12E—H12I···O6Eviii0.992.343.186 (2)142.3
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+1, z; (iv) x+3/2, y+1/2, z+1/2; (v) x+2, y+1, z+1; (vi) x+1, y+1, z+1; (vii) x, y+1, z+1; (viii) x1/2, y+1/2, z+1/2; (ix) x+3/2, y1/2, z+1/2.
 

Acknowledgements

TSY thanks the UOM for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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Volume 69| Part 10| October 2013| Pages o1572-o1573
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