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Acta Cryst. (2009). E65, o1560-o1561    [ doi:10.1107/S1600536809021692 ]

4-(But-3-enylamino)-3-nitrobenzoic acid

S. N. Narendra Babu, A. S. Abdul Rahim, H. Osman, S. R. Jebas and H.-K. Fun

Abstract top

The asymmetric unit of the title compound, C11H12N2O4, contains 12 crystallographically independent molecules, labelled A to L. The nitro and carboxyl groups are twisted slightly out of the plane of the attached benzene ring in all independent molecules except molecules G and D. The nitro group is coplanar with the benzene ring in molecule G and the carboxyl group is coplanar with the benzene ring in molecule D. The orientation of the butyl group with respect to the rest of the molecule is different in some of the independent molecules, with the C-C-C-C torsion angles varying from 104.2 (5) to 126.6 (7)°. In each independent molecule, an intramolecular N-H...O hydrogen bond generates an S(6) ring motif. In the crystal structure, the 12 independent molecules exist as six pairs of O-H...O hydrogen-bonded R22(8) dimers. In addition, C-H...O hydrogen bonds are observed.

Comment top

Various heterocyclic compounds of pharmacological interests (Ishida et al., 2006; Kuzniewski et al., 2008; Wu et al., 2000) can be synthesized by nitro benzoic acid derivatives as the precursors. We report here the crystal structure of the title compound, which was synthesized as an intermediate.

The asymmetric unit of the title compound (Fig. 1) comprises of twelve crystallographically independent molecules labelled as A to L. The bond lengths (Allen et al., 1987) and bond angles are normal. The nitro group (N2/O1/O2) is twisted away from the attached benzene ring (C1-C6) in eleven molecules forming dihedral angles of 1.54 (1)° in molecule A [5.45 (2)° in B; 4.68 (2)° in C; 2.44 (1) in D; 5.10 (2)° in E; 5.84 (2)° in F; 3.29 (2)° in H; 6.96 (2)° in I; 7.48 (2)° in J; 2.44 (2)° in K and 4.67 (2)° in L]. In molecule G, the nitro group (N2/O1/O2) is almost coplanar with the attached benzene ring (C1-C6) forming a dihedral angle of 0.99 (2)°. The dihedral angles formed by the carboxyl groups (C7/O3/O4) with the attached benzene rings are 5.24 (1)° in molecule A [4.49 (2)° in B; 1.69 (2)° in C; 19.79 (2)° in E; 18.38 (2)° in F; 16.46 (3)° in G; 15.11 (2)° in H; 27.26 (2)° in I; 28.61 (2)° in J; 16.39 (2)° in K; 21.94 (2)° in L], indicating that they are twisted from the mean plane of the benzene ring. In molecule D, the carboxyl group is coplanar with the benzene ring [dihedral angle 0.26 (1)°]. The orientation of the butyl group of the but-3-enylamino unit (N1/C8-C11) is different in some of the independent molecules. The C8-C9-C10-C11 torsion angle is -121.7 (5)° in molecule A [-109.4 (6)° in B; -107.0 (6)° in C; 126.3 (7)° in D; 123.7 (5)° in E; 123.0 (5)° in F; 126.6 (7)° in G; -104.2 (5)° in H; -112.9 (5)° in I; 111.6 (5)° in J; -104.8 (5)° in K and 121.8 (6)° in L]. In each independent molecule, an intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure, the twelve independent molecules exist as six pairs of O—H···O hydrogen-bonded R22(8) dimers (Table 1 and Fig. 3). In addition, C—H···O hydrogen bonds are observed.

Related literature top

For heterocyclic compounds of pharmacological interest, see: Ishida et al. (2006); Kuzniewski et al. (2008); Wu et al. (2000). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of ethyl 4-(but-3-enylamino)-3-nitro-benzoate (0.25 g, 0.001 mol) and KOH (0.112 g, 0.002 mol) was refluxed in aqueous ethanol (5 ml) for 3 h. After completion of the reaction, ethanol was distilled off and the reaction mixture was diluted with water (5 ml). The aqueous layer was washed with dichloromethane (5 ml × 2) and acidified with concentrated HCl to afford a yellow solid. Yellow single crystals were obtained after recrystallization of the crude product with hot ethyl acetate.

Refinement top

H atoms were positioned geometrically [C-H = 0.93–0.97 Å; N-H = 0.86Å and O-H = 0.82 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O). In the absence of significant anomalous scattering effects, 20703 Friedel pairs were averaged.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The twelve independent molecules in the asymmetric unit of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. One of the twelve independent molecules in the asymmetric unit to show clearly the atomic labelling. The other eleven molecules are labelled in a similar manner.
[Figure 3] Fig. 3. The crystal packing of the title compound, showing hydrogen-bonded (dashed lines) dimers.
4-(But-3-enylamino)-3-nitrobenzoic acid top
Crystal data top
C11H12N2O4F(000) = 5952
Mr = 236.23Dx = 1.427 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 9973 reflections
a = 13.3461 (5) Åθ = 2.7–33.0°
b = 66.777 (3) ŵ = 0.11 mm−1
c = 15.0195 (6) ÅT = 100 K
β = 99.632 (2)°Block, yellow
V = 13196.9 (9) Å30.33 × 0.29 × 0.13 mm
Z = 48
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		21275 independent reflections
Radiation source: fine-focus sealed tube16663 reflections with I > 2σ(I)
graphiteRint = 0.096
φ and ω scansθmax = 31.1°, θmin = 0.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −19→19
Tmin = 0.965, Tmax = 0.985k = −96→96
173518 measured reflectionsl = −21→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1104P)2 + 13.1603P]
where P = (Fo2 + 2Fc2)/3
21275 reflections(Δ/σ)max = 0.003
1837 parametersΔρmax = 0.73 e Å−3
2 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C11H12N2O4V = 13196.9 (9) Å3
Mr = 236.23Z = 48
Monoclinic, CcMo Kα radiation
a = 13.3461 (5) ŵ = 0.11 mm−1
b = 66.777 (3) ÅT = 100 K
c = 15.0195 (6) Å0.33 × 0.29 × 0.13 mm
β = 99.632 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		21275 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		16663 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.985Rint = 0.096
173518 measured reflectionsθmax = 31.1°
Refinement top
R[F2 > 2σ(F2)] = 0.078 w = 1/[σ2(Fo2) + (0.1104P)2 + 13.1603P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.213Δρmax = 0.73 e Å−3
S = 1.08Δρmin = −0.37 e Å−3
21275 reflectionsAbsolute structure: ?
1837 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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) top
xyzUiso*/Ueq
O1A0.4798 (2)−0.00716 (5)0.5335 (2)0.0206 (6)
O2A0.4840 (2)0.02449 (5)0.5645 (2)0.0198 (6)
O3A0.4556 (2)0.06616 (5)0.1916 (2)0.0225 (6)
H3AB0.45010.07820.18190.034*
O4A0.4515 (2)0.07584 (4)0.3347 (2)0.0200 (6)
N1A0.4905 (3)−0.01972 (5)0.3685 (2)0.0154 (6)
H1AA0.4904−0.02340.42340.018*
N2A0.4804 (2)0.01073 (5)0.5092 (2)0.0139 (6)
C1A0.4820 (3)−0.00012 (6)0.3488 (3)0.0135 (7)
C2A0.4790 (3)0.01539 (6)0.4155 (3)0.0127 (7)
C3A0.4705 (3)0.03555 (6)0.3914 (3)0.0128 (7)
H3AA0.46750.04520.43550.015*
C4A0.4666 (3)0.04124 (6)0.3024 (3)0.0136 (7)
C5A0.4696 (3)0.02653 (6)0.2357 (3)0.0142 (7)
H5AA0.46580.03030.17560.017*
C6A0.4781 (3)0.00665 (6)0.2594 (3)0.0157 (7)
H6AA0.4814−0.00280.21440.019*
C7A0.4571 (3)0.06271 (6)0.2777 (3)0.0163 (7)
C8A0.4999 (3)−0.03516 (6)0.3019 (3)0.0170 (7)
H8AA0.5488−0.03100.26440.020*
H8AB0.4349−0.03720.26310.020*
C9A0.5352 (3)−0.05477 (6)0.3505 (3)0.0225 (8)
H9AA0.5494−0.06450.30630.027*
H9AB0.5978−0.05230.39210.027*
C10A0.4590 (4)−0.06310 (6)0.4006 (3)0.0235 (9)
H10A0.3953−0.06590.36740.028*
C11A0.4722 (4)−0.06695 (7)0.4881 (3)0.0264 (9)
H11A0.5346−0.06440.52400.032*
H11B0.4192−0.07220.51360.032*
O1B0.1456 (3)0.20916 (5)0.1093 (2)0.0339 (8)
O2B0.1513 (3)0.18594 (5)0.0112 (2)0.0290 (7)
O3B0.1853 (3)0.11707 (5)0.0853 (2)0.0309 (8)
H3BB0.19510.10510.07730.046*
O4B0.2002 (3)0.10711 (5)0.2301 (2)0.0338 (8)
N1B0.1869 (3)0.20140 (6)0.2831 (3)0.0266 (8)
H1BA0.17170.21070.24340.032*
N2B0.1537 (3)0.19127 (6)0.0896 (3)0.0259 (8)
C1B0.1829 (3)0.18234 (7)0.2541 (3)0.0227 (9)
C2B0.1676 (3)0.17665 (7)0.1610 (3)0.0218 (8)
C3B0.1700 (3)0.15687 (7)0.1344 (3)0.0220 (8)
H3BA0.16240.15370.07330.026*
C4B0.1837 (3)0.14176 (7)0.1985 (3)0.0247 (9)
C5B0.1965 (3)0.14686 (7)0.2908 (3)0.0240 (9)
H5BA0.20600.13680.33430.029*
C6B0.1952 (3)0.16654 (7)0.3173 (3)0.0253 (9)
H6BA0.20270.16950.37860.030*
C7B0.1905 (3)0.12053 (7)0.1718 (3)0.0246 (9)
C8B0.2151 (4)0.20750 (8)0.3773 (3)0.0308 (10)
H8BA0.27060.19920.40690.037*
H8BB0.15780.20570.40860.037*
C9B0.2469 (4)0.22914 (8)0.3813 (4)0.0347 (11)
H9BA0.30240.23090.34780.042*
H9BB0.27120.23290.44360.042*
C10B0.1595 (4)0.24261 (7)0.3423 (3)0.0286 (10)
H10B0.10660.24420.37490.034*
C11B0.1537 (5)0.25217 (9)0.2657 (4)0.0429 (13)
H11C0.20550.25090.23160.051*
H11D0.09780.26030.24530.051*
O1C0.4371 (3)0.20715 (5)0.2700 (2)0.0309 (8)
O2C0.4437 (3)0.18319 (5)0.3684 (2)0.0276 (7)
O3C0.4531 (3)0.11428 (5)0.2970 (2)0.0254 (7)
H3CB0.45700.10220.30630.038*
O4C0.4392 (3)0.10425 (5)0.1523 (2)0.0272 (7)
N1C0.4024 (3)0.19865 (6)0.0965 (2)0.0222 (7)
H1CA0.40720.20790.13670.027*
N2C0.4381 (3)0.18899 (6)0.2901 (3)0.0222 (7)
C1C0.4165 (3)0.17956 (6)0.1254 (3)0.0200 (8)
C2C0.4323 (3)0.17402 (6)0.2187 (3)0.0181 (7)
C3C0.4406 (3)0.15417 (6)0.2457 (3)0.0181 (7)
H3CA0.44940.15110.30690.022*
C4C0.4362 (3)0.13885 (6)0.1829 (3)0.0184 (7)
C5C0.4237 (3)0.14409 (6)0.0905 (3)0.0190 (8)
H5CA0.42190.13400.04740.023*
C6C0.4144 (3)0.16358 (7)0.0631 (3)0.0206 (8)
H6CA0.40640.16650.00180.025*
C7C0.4439 (3)0.11772 (6)0.2093 (3)0.0203 (8)
C8C0.3795 (4)0.20470 (7)0.0011 (3)0.0235 (9)
H8CA0.33040.1956−0.03210.028*
H8CB0.44090.2043−0.02550.028*
C9C0.3365 (4)0.22596 (7)−0.0039 (3)0.0257 (9)
H9CA0.31470.2296−0.06670.031*
H9CB0.27740.22630.02580.031*
C10C0.4126 (4)0.24106 (7)0.0396 (3)0.0266 (9)
H10C0.46560.24440.00930.032*
C11C0.4099 (5)0.24996 (8)0.1176 (4)0.0392 (12)
H11E0.35800.24700.14990.047*
H11F0.45980.25920.14040.047*
O1D0.6730 (3)0.17158 (5)0.3481 (2)0.0273 (7)
O2D0.6851 (3)0.13975 (5)0.3179 (2)0.0263 (7)
O3D0.7302 (3)0.09808 (5)0.6904 (2)0.0242 (6)
H3DB0.73860.08600.69970.036*
O4D0.7298 (2)0.08858 (5)0.5475 (2)0.0211 (6)
N1D0.6674 (3)0.18377 (5)0.5140 (3)0.0239 (8)
H1DA0.66280.18750.45860.029*
N2D0.6820 (3)0.15353 (5)0.3716 (2)0.0193 (7)
C1D0.6813 (3)0.16414 (6)0.5324 (3)0.0191 (8)
C2D0.6873 (3)0.14896 (7)0.4670 (3)0.0185 (8)
C3D0.7010 (3)0.12866 (6)0.4903 (3)0.0165 (7)
H3DA0.70410.11910.44570.020*
C4D0.7096 (3)0.12290 (6)0.5797 (3)0.0176 (7)
C5D0.7035 (3)0.13769 (7)0.6457 (3)0.0197 (8)
H5DA0.70930.13390.70580.024*
C6D0.6893 (3)0.15745 (7)0.6238 (3)0.0199 (8)
H6DA0.68470.16670.66920.024*
C7D0.7249 (3)0.10172 (6)0.6044 (3)0.0191 (8)
C8D0.6595 (4)0.19921 (7)0.5817 (3)0.0296 (10)
H8DA0.72640.20220.61530.036*
H8DB0.61710.19450.62380.036*
C9D0.6126 (5)0.21821 (8)0.5334 (4)0.0446 (14)
H9DA0.54860.21490.49540.054*
H9DB0.59910.22800.57780.054*
C10D0.6831 (5)0.22691 (9)0.4773 (4)0.0415 (13)
H10D0.74940.22960.50490.050*
C11D0.6572 (6)0.23101 (10)0.3901 (4)0.0476 (15)
H11G0.59150.22840.36070.057*
H11H0.70480.23650.35840.057*
O1E0.9368 (3)0.16267 (5)0.5327 (2)0.0292 (7)
O2E0.9200 (3)0.19429 (5)0.5618 (2)0.0319 (8)
O3E0.8969 (3)0.23643 (5)0.1892 (2)0.0280 (7)
H3EB0.89200.24850.18040.042*
O4E0.9056 (3)0.24640 (5)0.3334 (2)0.0277 (7)
N1E0.9343 (3)0.15003 (6)0.3660 (3)0.0224 (7)
H1EA0.93780.14620.42110.027*
N2E0.9277 (3)0.18051 (6)0.5081 (3)0.0239 (8)
C1E0.9296 (3)0.16985 (7)0.3479 (3)0.0202 (8)
C2E0.9259 (3)0.18532 (7)0.4136 (3)0.0206 (8)
C3E0.9181 (3)0.20535 (7)0.3901 (3)0.0224 (8)
H3EA0.91540.21490.43450.027*
C4E0.9143 (3)0.21133 (7)0.3012 (3)0.0245 (9)
C5E0.9188 (3)0.19634 (7)0.2340 (3)0.0228 (9)
H5EA0.91650.20010.17410.027*
C6E0.9265 (3)0.17648 (7)0.2571 (3)0.0230 (8)
H6EA0.92990.16700.21230.028*
C7E0.9050 (3)0.23280 (6)0.2758 (3)0.0217 (8)
C8E0.9334 (4)0.13490 (7)0.2961 (3)0.0271 (9)
H8EA0.99500.13590.27010.033*
H8EB0.87590.13710.24840.033*
C9E0.9262 (4)0.11393 (7)0.3369 (3)0.0298 (10)
H9EA0.86210.11280.35880.036*
H9EB0.92590.10400.28950.036*
C10E1.0104 (4)0.10915 (7)0.4123 (4)0.0310 (10)
H10E1.07690.11000.40170.037*
C11E0.9950 (5)0.10372 (9)0.4936 (4)0.0404 (13)
H11I0.92910.10270.50580.048*
H11J1.05000.10090.53860.048*
O1F0.1889 (3)0.34007 (5)0.3495 (2)0.0281 (7)
O2F0.1725 (3)0.30852 (5)0.3170 (2)0.0294 (7)
O3F0.1606 (3)0.26731 (5)0.6860 (2)0.0278 (7)
H3FB0.15960.25520.69420.042*
O4F0.1696 (3)0.25744 (5)0.5453 (2)0.0277 (7)
N1F0.1790 (3)0.35313 (5)0.5138 (2)0.0204 (7)
H1FA0.18420.35670.45970.024*
N2F0.1788 (3)0.32233 (6)0.3722 (3)0.0236 (8)
C1F0.1768 (3)0.33346 (6)0.5321 (3)0.0184 (8)
C2F0.1754 (3)0.31797 (7)0.4668 (3)0.0213 (8)
C3F0.1717 (3)0.29781 (7)0.4894 (3)0.0222 (8)
H3FA0.17040.28810.44490.027*
C4F0.1699 (4)0.29217 (7)0.5777 (3)0.0220 (8)
C5F0.1712 (3)0.30720 (6)0.6434 (3)0.0214 (8)
H5FA0.16880.30350.70270.026*
C6F0.1758 (3)0.32710 (6)0.6230 (3)0.0187 (8)
H6FA0.17820.33660.66860.022*
C7F0.1671 (3)0.27088 (6)0.6022 (3)0.0203 (8)
C8F0.1731 (3)0.36891 (6)0.5800 (3)0.0224 (8)
H8FA0.23850.37040.61880.027*
H8FB0.12320.36540.61750.027*
C9F0.1428 (3)0.38856 (6)0.5307 (3)0.0206 (8)
H9FA0.07980.38660.48900.025*
H9FB0.13090.39860.57430.025*
C10F0.2228 (4)0.39591 (7)0.4798 (3)0.0242 (9)
H10F0.28760.39800.51230.029*
C11F0.2083 (4)0.39967 (7)0.3924 (4)0.0292 (10)
H11K0.14440.39780.35770.035*
H11L0.26190.40420.36540.035*
O1G0.4258 (3)0.32758 (5)0.5320 (2)0.0301 (7)
O2G0.4339 (3)0.35946 (5)0.5614 (2)0.0287 (7)
O4G0.4637 (2)0.40970 (5)0.3370 (2)0.0236 (7)
O3G0.4661 (3)0.39941 (5)0.1950 (2)0.0291 (7)
H3GB0.47080.41150.18680.044*
N1G0.4256 (3)0.31428 (6)0.3676 (3)0.0261 (8)
H1GA0.42260.31090.42220.031*
N2G0.4334 (3)0.34537 (6)0.5087 (2)0.0228 (7)
C1G0.4356 (3)0.33379 (7)0.3488 (3)0.0221 (8)
C2G0.4396 (3)0.34948 (6)0.4150 (3)0.0194 (8)
C3G0.4483 (3)0.36957 (6)0.3917 (3)0.0189 (8)
H3GA0.45100.37950.43560.023*
C4G0.4528 (3)0.37475 (7)0.3034 (3)0.0206 (8)
C5G0.4492 (3)0.35973 (7)0.2371 (3)0.0223 (8)
H5GA0.45240.36330.17770.027*
C6G0.4412 (3)0.34012 (7)0.2590 (3)0.0233 (8)
H6GA0.43920.33050.21400.028*
C7G0.4614 (3)0.39604 (7)0.2795 (3)0.0220 (8)
C8G0.4195 (5)0.29851 (8)0.2980 (3)0.0348 (11)
H8GA0.48370.29750.27620.042*
H8GB0.36690.30180.24730.042*
C9G0.3948 (6)0.27852 (10)0.3394 (5)0.0552 (17)
H9GA0.32930.27960.35890.066*
H9GB0.38980.26820.29370.066*
C10G0.4694 (6)0.27285 (10)0.4144 (5)0.0537 (17)
H10G0.53710.27240.40690.064*
C11G0.4460 (7)0.26813 (10)0.4959 (5)0.0580 (19)
H11M0.37870.26850.50480.070*
H11N0.49710.26450.54310.070*
O1H0.6949 (2)0.37269 (5)0.1115 (2)0.0233 (6)
O2H0.6687 (3)0.34912 (5)0.0112 (2)0.0277 (7)
O3H0.6506 (3)0.28037 (5)0.0834 (2)0.0298 (7)
H3HB0.64560.26830.07450.045*
O4H0.6609 (3)0.27052 (5)0.2283 (2)0.0310 (8)
N1H0.7181 (3)0.36459 (5)0.2845 (3)0.0197 (7)
H1HA0.71740.37390.24470.024*
N2H0.6824 (3)0.35480 (5)0.0906 (2)0.0185 (7)
C1H0.7002 (3)0.34570 (6)0.2547 (3)0.0170 (7)
C2H0.6824 (3)0.34006 (6)0.1616 (3)0.0185 (7)
C3H0.6687 (3)0.32022 (7)0.1345 (3)0.0216 (8)
H3HA0.65900.31700.07340.026*
C4H0.6694 (3)0.30522 (6)0.1979 (3)0.0215 (8)
C5H0.6843 (3)0.31012 (7)0.2905 (3)0.0223 (8)
H5HA0.68460.30000.33320.027*
C6H0.6984 (3)0.32972 (6)0.3180 (3)0.0199 (8)
H6HA0.70710.33270.37940.024*
C7H0.6595 (4)0.28398 (6)0.1702 (3)0.0247 (9)
C8H0.7385 (3)0.37048 (7)0.3792 (3)0.0223 (8)
H8HA0.78370.36090.41380.027*
H8HB0.67560.37090.40350.027*
C9H0.7880 (3)0.39128 (6)0.3861 (3)0.0200 (8)
H9HA0.80560.39500.44920.024*
H9HB0.85030.39080.36080.024*
C10H0.7186 (3)0.40677 (6)0.3371 (3)0.0210 (8)
H10H0.66510.41130.36420.025*
C11H0.7283 (4)0.41445 (8)0.2579 (4)0.0310 (10)
H11O0.78100.41030.22890.037*
H11P0.68240.42400.23110.037*
O1I0.9871 (3)0.37631 (5)0.2729 (2)0.0249 (7)
O2I0.9665 (2)0.35322 (5)0.3704 (2)0.0252 (7)
O3I0.9224 (3)0.28461 (5)0.2946 (2)0.0305 (8)
H3IB0.91730.27260.30310.046*
O4I0.8981 (3)0.27468 (5)0.1495 (2)0.0325 (8)
N1I0.9359 (3)0.36902 (5)0.0990 (2)0.0185 (7)
H1IA0.95680.37810.13850.022*
N2I0.9692 (3)0.35869 (5)0.2916 (2)0.0180 (7)
C1I0.9348 (3)0.34994 (6)0.1276 (3)0.0187 (8)
C2I0.9492 (3)0.34421 (6)0.2196 (3)0.0185 (8)
C3I0.9418 (3)0.32425 (6)0.2460 (3)0.0193 (8)
H3IA0.95000.32100.30700.023*
C4I0.9222 (3)0.30932 (6)0.1815 (3)0.0200 (8)
C5I0.9102 (3)0.31459 (7)0.0897 (3)0.0238 (9)
H5IA0.89770.30460.04610.029*
C6I0.9163 (3)0.33419 (7)0.0627 (3)0.0216 (8)
H6IA0.90840.33720.00150.026*
C7I0.9145 (4)0.28810 (7)0.2073 (3)0.0242 (9)
C8I0.9044 (3)0.37542 (7)0.0059 (3)0.0220 (8)
H8IA0.84480.3679−0.02140.026*
H8IB0.95840.3728−0.02850.026*
C9I0.8800 (3)0.39791 (6)0.0041 (3)0.0222 (8)
H9IA0.85320.4019−0.05730.027*
H9IB0.82800.40040.04080.027*
C10I0.9712 (3)0.41012 (7)0.0385 (3)0.0235 (9)
H10I1.02310.41040.00430.028*
C11I0.9845 (4)0.42081 (8)0.1151 (4)0.0301 (10)
H11Q0.93430.42090.15120.036*
H11R1.04400.42810.13210.036*
O1J0.6912 (2)−0.04212 (5)0.6067 (2)0.0218 (6)
O2J0.7066 (2)−0.01889 (5)0.5094 (2)0.0202 (6)
O3J0.7274 (3)0.05019 (5)0.5851 (2)0.0235 (6)
H3JB0.72940.06230.57670.035*
O4J0.7450 (3)0.05988 (5)0.7296 (2)0.0254 (7)
N1J0.7383 (3)−0.03462 (5)0.7804 (2)0.0166 (6)
H1JA0.7226−0.04380.74050.020*
N2J0.7042 (2)−0.02428 (5)0.5882 (2)0.0153 (6)
C1J0.7335 (3)−0.01560 (6)0.7525 (2)0.0115 (6)
C2J0.7178 (3)−0.00976 (6)0.6585 (2)0.0129 (7)
C3J0.7194 (3)0.01032 (6)0.6330 (3)0.0142 (7)
H3JA0.71060.01360.57210.017*
C4J0.7341 (3)0.02532 (6)0.6973 (3)0.0156 (7)
C5J0.7469 (3)0.02006 (6)0.7898 (3)0.0163 (7)
H5JA0.75550.03010.83340.020*
C6J0.7468 (3)0.00046 (6)0.8159 (3)0.0160 (7)
H6JA0.7556−0.00250.87720.019*
C7J0.7362 (3)0.04660 (6)0.6716 (3)0.0166 (7)
C8J0.7683 (3)−0.04080 (7)0.8742 (3)0.0208 (8)
H8JA0.7124−0.03880.90700.025*
H8JB0.8256−0.03280.90280.025*
C9J0.7975 (3)−0.06297 (6)0.8762 (3)0.0208 (8)
H9JA0.8509−0.06490.84050.025*
H9JB0.8241−0.06680.93790.025*
C10J0.7098 (3)−0.07612 (7)0.8404 (3)0.0247 (9)
H10J0.6582−0.07710.87480.030*
C11J0.6981 (4)−0.08646 (8)0.7652 (4)0.0336 (11)
H11S0.7476−0.08600.72840.040*
H11T0.6403−0.09430.74860.040*
O1K0.4841 (2)0.53994 (5)0.2662 (2)0.0248 (7)
O2K0.4993 (3)0.51635 (5)0.3670 (2)0.0246 (7)
O3K0.4947 (3)0.44726 (5)0.2956 (2)0.0264 (7)
H3KB0.49580.43510.30470.040*
O4K0.4824 (3)0.43708 (5)0.1518 (3)0.0308 (8)
N1K0.4536 (3)0.53129 (5)0.0940 (2)0.0175 (7)
H1KA0.45800.54060.13400.021*
N2K0.4897 (2)0.52186 (6)0.2871 (2)0.0169 (6)
C1K0.4668 (3)0.51243 (6)0.1231 (3)0.0147 (7)
C2K0.4841 (3)0.50701 (6)0.2170 (3)0.0156 (7)
C3K0.4928 (3)0.48703 (6)0.2444 (3)0.0151 (7)
H3KA0.50370.48400.30570.018*
C4K0.4854 (3)0.47175 (6)0.1821 (3)0.0167 (7)
C5K0.4724 (3)0.47678 (6)0.0893 (3)0.0176 (7)
H5KA0.46940.46660.04660.021*
C6K0.4642 (3)0.49629 (6)0.0614 (2)0.0158 (7)
H6KA0.45680.4991−0.00010.019*
C7K0.4884 (3)0.45065 (7)0.2100 (3)0.0191 (8)
C8K0.4319 (3)0.53727 (6)−0.0015 (3)0.0183 (7)
H8KA0.38370.5280−0.03510.022*
H8KB0.49390.5369−0.02720.022*
C9K0.3878 (3)0.55848 (7)−0.0079 (3)0.0213 (8)
H9KA0.36930.5622−0.07100.026*
H9KB0.32660.55870.01900.026*
C10K0.4616 (3)0.57339 (7)0.0388 (3)0.0264 (9)
H10K0.51540.57720.01030.032*
C11K0.4558 (4)0.58158 (8)0.1179 (4)0.0353 (11)
H11U0.40300.57810.14820.042*
H11V0.50460.59080.14330.042*
O1L0.2305 (3)−0.00317 (5)−0.1522 (2)0.0248 (7)
O2L0.2347 (3)0.02862 (5)−0.1806 (2)0.0273 (7)
O4L0.2148 (2)0.07949 (5)0.0451 (2)0.0256 (7)
O3L0.2203 (3)0.06950 (5)0.1883 (2)0.0277 (7)
H3LB0.21870.08160.19660.042*
N1L0.2342 (3)−0.01613 (5)0.0147 (2)0.0182 (7)
H1LA0.2352−0.0198−0.04010.022*
N2L0.2309 (3)0.01460 (5)−0.1266 (2)0.0182 (7)
C1L0.2281 (3)0.00347 (6)0.0321 (3)0.0161 (7)
C2L0.2269 (3)0.01911 (6)−0.0334 (3)0.0166 (7)
C3L0.2234 (3)0.03931 (6)−0.0102 (3)0.0177 (8)
H3LA0.22230.0491−0.05430.021*
C4L0.2214 (3)0.04480 (6)0.0785 (3)0.0160 (7)
C5L0.2211 (3)0.02969 (6)0.1438 (3)0.0179 (8)
H5LA0.21850.03330.20320.021*
C6L0.2246 (3)0.00993 (7)0.1218 (3)0.0188 (8)
H6LA0.22470.00040.16690.023*
C7L0.2189 (3)0.06601 (6)0.1037 (3)0.0184 (7)
C8L0.2391 (3)−0.03163 (7)0.0840 (3)0.0217 (8)
H8LA0.1769−0.03150.10940.026*
H8LB0.2954−0.02890.13220.026*
C9L0.2532 (4)−0.05211 (7)0.0439 (3)0.0291 (10)
H9LA0.3177−0.05230.02220.035*
H9LB0.2563−0.06210.09120.035*
C10L0.1710 (4)−0.05764 (8)−0.0316 (4)0.0318 (11)
H10L0.1049−0.0579−0.01970.038*
C11L0.1844 (5)−0.06217 (9)−0.1135 (4)0.0395 (13)
H11W0.2495−0.0621−0.12810.047*
H11X0.1290−0.0655−0.15720.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0284 (16)0.0177 (14)0.0163 (15)0.0009 (11)0.0062 (11)0.0026 (11)
O2A0.0267 (15)0.0179 (14)0.0146 (14)0.0035 (11)0.0031 (11)−0.0001 (11)
O3A0.0347 (17)0.0170 (14)0.0172 (14)0.0002 (12)0.0084 (12)0.0030 (11)
O4A0.0266 (15)0.0151 (13)0.0193 (14)0.0011 (11)0.0066 (11)−0.0014 (11)
N1A0.0199 (16)0.0136 (15)0.0124 (16)0.0004 (12)0.0019 (12)0.0006 (11)
N2A0.0163 (15)0.0151 (15)0.0104 (15)0.0007 (11)0.0028 (11)−0.0020 (11)
C1A0.0128 (16)0.0147 (17)0.0132 (17)−0.0003 (12)0.0030 (12)−0.0016 (13)
C2A0.0150 (16)0.0120 (16)0.0118 (17)−0.0010 (12)0.0040 (13)−0.0002 (12)
C3A0.0161 (17)0.0129 (16)0.0096 (16)−0.0007 (12)0.0026 (12)−0.0022 (12)
C4A0.0143 (16)0.0120 (16)0.0144 (18)0.0007 (12)0.0020 (13)0.0020 (13)
C5A0.0174 (17)0.0153 (17)0.0107 (17)0.0007 (13)0.0050 (13)0.0023 (13)
C6A0.0189 (18)0.0142 (17)0.0145 (19)−0.0008 (13)0.0044 (13)−0.0018 (13)
C7A0.0168 (17)0.0184 (18)0.0148 (18)−0.0016 (13)0.0059 (13)0.0018 (13)
C8A0.0208 (19)0.0176 (18)0.0134 (18)−0.0004 (14)0.0053 (14)−0.0028 (13)
C9A0.026 (2)0.0182 (19)0.024 (2)0.0037 (15)0.0068 (16)0.0008 (15)
C10A0.028 (2)0.0145 (18)0.027 (2)−0.0028 (15)0.0034 (17)−0.0013 (15)
C11A0.031 (2)0.024 (2)0.025 (2)−0.0019 (17)0.0085 (18)0.0016 (17)
O1B0.055 (2)0.0258 (17)0.0205 (18)−0.0025 (15)0.0039 (15)0.0023 (13)
O2B0.0396 (19)0.0329 (18)0.0142 (15)0.0002 (14)0.0034 (13)−0.0018 (12)
O3B0.042 (2)0.0278 (17)0.0241 (17)0.0009 (15)0.0092 (14)−0.0020 (13)
O4B0.052 (2)0.0238 (16)0.0250 (17)0.0044 (15)0.0064 (15)0.0007 (13)
N1B0.035 (2)0.0255 (19)0.0183 (19)−0.0018 (15)0.0013 (15)−0.0035 (14)
N2B0.0268 (19)0.032 (2)0.0174 (18)0.0015 (15)0.0005 (14)0.0004 (15)
C1B0.023 (2)0.033 (2)0.0122 (18)−0.0021 (16)0.0026 (14)−0.0018 (15)
C2B0.022 (2)0.027 (2)0.0162 (19)−0.0031 (16)0.0018 (15)−0.0005 (15)
C3B0.0191 (19)0.029 (2)0.0174 (19)−0.0033 (16)0.0013 (14)−0.0022 (15)
C4B0.020 (2)0.029 (2)0.024 (2)−0.0029 (16)0.0023 (16)−0.0012 (16)
C5B0.023 (2)0.033 (2)0.0162 (19)−0.0031 (17)0.0025 (15)−0.0015 (16)
C6B0.024 (2)0.031 (2)0.020 (2)−0.0076 (17)0.0024 (16)−0.0025 (17)
C7B0.021 (2)0.028 (2)0.025 (2)−0.0013 (16)0.0047 (16)−0.0011 (16)
C8B0.037 (3)0.039 (3)0.016 (2)0.002 (2)0.0010 (17)−0.0082 (18)
C9B0.036 (3)0.043 (3)0.026 (2)−0.003 (2)0.0057 (19)−0.015 (2)
C10B0.033 (2)0.027 (2)0.026 (2)−0.0045 (18)0.0051 (18)−0.0105 (18)
C11B0.039 (3)0.049 (3)0.039 (3)−0.011 (2)0.004 (2)0.006 (2)
O1C0.053 (2)0.0191 (16)0.0193 (17)0.0006 (14)0.0014 (14)−0.0019 (12)
O2C0.044 (2)0.0255 (16)0.0123 (15)−0.0013 (14)0.0026 (13)−0.0019 (12)
O3C0.0407 (19)0.0181 (14)0.0173 (15)−0.0005 (13)0.0051 (13)0.0016 (11)
O4C0.046 (2)0.0169 (14)0.0200 (15)0.0008 (13)0.0081 (14)−0.0003 (11)
N1C0.0298 (19)0.0221 (18)0.0131 (17)0.0006 (14)−0.0011 (13)0.0014 (13)
N2C0.0295 (19)0.0201 (17)0.0159 (17)0.0000 (14)0.0010 (13)−0.0003 (13)
C1C0.0185 (19)0.0205 (19)0.020 (2)−0.0003 (14)−0.0011 (14)0.0010 (15)
C2C0.0179 (18)0.0214 (19)0.0137 (18)0.0005 (14)−0.0010 (13)−0.0028 (14)
C3C0.0171 (18)0.025 (2)0.0118 (17)0.0001 (14)0.0007 (13)−0.0007 (14)
C4C0.0168 (18)0.0185 (18)0.0202 (19)−0.0025 (14)0.0040 (14)−0.0005 (14)
C5C0.0209 (19)0.0200 (19)0.0167 (19)0.0013 (14)0.0053 (14)−0.0021 (14)
C6C0.026 (2)0.024 (2)0.0113 (17)0.0000 (16)0.0019 (14)−0.0012 (14)
C7C0.0202 (19)0.0203 (19)0.0200 (19)0.0004 (15)0.0024 (15)0.0006 (14)
C8C0.036 (2)0.021 (2)0.0124 (19)−0.0035 (17)0.0027 (16)0.0028 (14)
C9C0.032 (2)0.025 (2)0.019 (2)0.0000 (17)0.0002 (16)0.0059 (16)
C10C0.030 (2)0.018 (2)0.029 (2)0.0019 (16)−0.0010 (17)0.0039 (17)
C11C0.043 (3)0.035 (3)0.037 (3)0.003 (2)0.000 (2)−0.008 (2)
O1D0.043 (2)0.0209 (15)0.0182 (16)−0.0040 (13)0.0069 (13)0.0036 (12)
O2D0.0356 (18)0.0252 (16)0.0180 (15)−0.0035 (13)0.0044 (12)−0.0039 (12)
O3D0.0329 (17)0.0230 (15)0.0166 (15)0.0005 (13)0.0042 (12)0.0019 (11)
O4D0.0269 (16)0.0188 (14)0.0176 (15)0.0028 (11)0.0037 (11)−0.0007 (11)
N1D0.038 (2)0.0195 (17)0.0149 (17)−0.0031 (15)0.0046 (14)−0.0009 (13)
N2D0.0230 (17)0.0188 (16)0.0157 (17)−0.0042 (13)0.0018 (13)−0.0014 (12)
C1D0.0194 (19)0.0182 (18)0.020 (2)−0.0046 (14)0.0049 (15)−0.0013 (14)
C2D0.0183 (18)0.024 (2)0.0127 (18)−0.0010 (14)0.0015 (14)−0.0007 (14)
C3D0.0123 (17)0.0176 (18)0.0194 (19)−0.0016 (13)0.0015 (13)−0.0015 (14)
C4D0.0155 (17)0.0173 (18)0.0197 (19)−0.0005 (14)0.0023 (14)−0.0012 (14)
C5D0.0152 (18)0.025 (2)0.018 (2)−0.0033 (15)−0.0004 (14)−0.0007 (15)
C6D0.0188 (18)0.026 (2)0.0140 (18)−0.0043 (15)0.0014 (14)−0.0014 (15)
C7D0.0141 (17)0.0228 (19)0.021 (2)−0.0001 (14)0.0054 (14)−0.0026 (15)
C8D0.049 (3)0.019 (2)0.021 (2)−0.0059 (19)0.0079 (19)−0.0018 (16)
C9D0.068 (4)0.037 (3)0.031 (3)−0.005 (3)0.015 (3)−0.006 (2)
C10D0.052 (3)0.039 (3)0.033 (3)−0.018 (3)0.004 (2)−0.001 (2)
C11D0.070 (4)0.045 (3)0.030 (3)−0.009 (3)0.013 (3)0.005 (3)
O1E0.044 (2)0.0240 (17)0.0203 (16)−0.0058 (14)0.0077 (14)0.0004 (13)
O2E0.048 (2)0.0303 (18)0.0170 (16)−0.0088 (15)0.0059 (14)−0.0063 (13)
O3E0.0410 (19)0.0214 (16)0.0210 (16)0.0018 (13)0.0032 (13)0.0016 (12)
O4E0.0409 (19)0.0202 (15)0.0239 (17)0.0034 (13)0.0109 (14)−0.0020 (12)
N1E0.0270 (19)0.0189 (17)0.0206 (18)−0.0020 (14)0.0017 (14)−0.0031 (13)
N2E0.0252 (18)0.0263 (19)0.0185 (18)−0.0045 (14)−0.0016 (14)−0.0034 (14)
C1E0.0182 (19)0.022 (2)0.020 (2)−0.0044 (15)0.0021 (14)−0.0019 (15)
C2E0.021 (2)0.022 (2)0.018 (2)−0.0012 (15)0.0021 (15)−0.0004 (15)
C3E0.022 (2)0.029 (2)0.015 (2)−0.0044 (16)0.0010 (15)−0.0026 (16)
C4E0.028 (2)0.023 (2)0.021 (2)0.0012 (16)0.0015 (16)0.0004 (16)
C5E0.034 (2)0.022 (2)0.0115 (19)0.0008 (16)0.0014 (15)−0.0007 (15)
C6E0.027 (2)0.022 (2)0.019 (2)−0.0020 (16)0.0026 (16)−0.0011 (16)
C7E0.029 (2)0.021 (2)0.0156 (19)−0.0013 (16)0.0022 (15)0.0025 (15)
C8E0.033 (2)0.025 (2)0.024 (2)−0.0038 (18)0.0051 (18)−0.0059 (17)
C9E0.036 (3)0.024 (2)0.031 (2)−0.0097 (18)0.0103 (19)−0.0090 (17)
C10E0.035 (3)0.018 (2)0.043 (3)0.0016 (18)0.014 (2)0.0043 (18)
C11E0.049 (3)0.041 (3)0.032 (3)−0.005 (2)0.008 (2)0.000 (2)
O1F0.042 (2)0.0228 (16)0.0207 (16)−0.0007 (14)0.0095 (14)0.0061 (13)
O2F0.044 (2)0.0303 (18)0.0144 (15)−0.0058 (15)0.0046 (13)−0.0075 (12)
O3F0.047 (2)0.0190 (15)0.0183 (16)−0.0027 (13)0.0084 (14)0.0034 (12)
O4F0.043 (2)0.0189 (15)0.0206 (16)−0.0015 (13)0.0049 (13)−0.0017 (12)
N1F0.0278 (18)0.0176 (16)0.0169 (17)−0.0007 (13)0.0067 (13)0.0001 (12)
N2F0.0234 (18)0.029 (2)0.0197 (19)−0.0005 (14)0.0062 (14)0.0040 (14)
C1F0.0192 (18)0.0204 (19)0.0152 (19)0.0005 (14)0.0019 (14)0.0020 (14)
C2F0.023 (2)0.026 (2)0.0142 (19)0.0001 (16)0.0025 (14)0.0017 (15)
C3F0.021 (2)0.020 (2)0.024 (2)−0.0023 (15)0.0030 (16)0.0019 (16)
C4F0.031 (2)0.024 (2)0.0113 (18)−0.0021 (16)0.0044 (15)−0.0032 (15)
C5F0.031 (2)0.020 (2)0.0122 (19)−0.0016 (16)0.0011 (15)−0.0027 (14)
C6F0.0215 (19)0.0216 (19)0.0126 (18)0.0022 (15)0.0021 (14)0.0041 (14)
C7F0.029 (2)0.0159 (18)0.0164 (19)0.0030 (15)0.0038 (15)0.0019 (14)
C8F0.028 (2)0.021 (2)0.0188 (19)−0.0008 (16)0.0078 (16)0.0008 (15)
C9F0.030 (2)0.0165 (17)0.0173 (18)0.0013 (15)0.0084 (15)0.0018 (13)
C10F0.028 (2)0.024 (2)0.021 (2)−0.0046 (17)0.0053 (16)0.0016 (15)
C11F0.031 (2)0.028 (2)0.031 (3)−0.0020 (18)0.0084 (19)0.0032 (18)
O1G0.040 (2)0.0308 (18)0.0200 (17)−0.0060 (14)0.0064 (14)−0.0004 (13)
O2G0.0388 (19)0.0277 (16)0.0194 (16)−0.0006 (14)0.0040 (13)−0.0038 (12)
O4G0.0254 (16)0.0211 (15)0.0253 (16)−0.0008 (12)0.0070 (12)−0.0039 (12)
O3G0.0375 (19)0.0282 (17)0.0236 (17)−0.0035 (14)0.0110 (14)0.0039 (13)
N1G0.035 (2)0.0245 (18)0.0182 (18)−0.0031 (15)0.0022 (15)−0.0009 (14)
N2G0.0249 (18)0.0288 (19)0.0137 (17)−0.0020 (14)0.0007 (13)−0.0030 (13)
C1G0.0180 (19)0.025 (2)0.022 (2)0.0000 (15)0.0000 (15)−0.0020 (16)
C2G0.0221 (19)0.0218 (19)0.0142 (18)−0.0002 (15)0.0034 (14)0.0003 (14)
C3G0.0174 (18)0.024 (2)0.0150 (18)0.0011 (15)0.0022 (14)−0.0049 (14)
C4G0.0157 (18)0.024 (2)0.022 (2)0.0016 (15)0.0026 (15)0.0045 (15)
C5G0.020 (2)0.029 (2)0.018 (2)0.0043 (16)0.0038 (15)0.0023 (16)
C6G0.024 (2)0.028 (2)0.018 (2)0.0022 (17)0.0047 (16)−0.0037 (16)
C7G0.0145 (17)0.030 (2)0.023 (2)0.0005 (15)0.0061 (15)0.0000 (16)
C8G0.053 (3)0.028 (2)0.024 (2)−0.007 (2)0.009 (2)−0.0054 (18)
C9G0.072 (5)0.046 (3)0.051 (4)−0.023 (3)0.018 (3)−0.013 (3)
C10G0.067 (5)0.036 (3)0.062 (4)−0.013 (3)0.023 (4)−0.003 (3)
C11G0.097 (6)0.046 (4)0.033 (3)−0.019 (4)0.015 (3)0.001 (3)
O1H0.0326 (17)0.0159 (14)0.0209 (16)−0.0022 (12)0.0025 (12)−0.0001 (11)
O2H0.042 (2)0.0261 (16)0.0149 (15)0.0049 (14)0.0041 (13)−0.0010 (12)
O3H0.048 (2)0.0200 (16)0.0207 (17)−0.0012 (14)0.0049 (14)−0.0063 (12)
O4H0.055 (2)0.0154 (15)0.0228 (17)−0.0018 (14)0.0068 (15)0.0016 (12)
N1H0.0261 (18)0.0141 (15)0.0184 (17)0.0007 (13)0.0023 (13)−0.0007 (12)
N2H0.0167 (16)0.0203 (17)0.0187 (17)0.0030 (12)0.0037 (12)0.0041 (13)
C1H0.0155 (17)0.0198 (19)0.0159 (18)0.0025 (14)0.0033 (14)−0.0008 (14)
C2H0.0178 (18)0.0207 (19)0.0168 (19)0.0010 (14)0.0025 (14)0.0002 (14)
C3H0.021 (2)0.022 (2)0.021 (2)−0.0001 (15)0.0034 (15)−0.0037 (16)
C4H0.026 (2)0.0173 (19)0.020 (2)−0.0012 (15)0.0024 (15)−0.0024 (15)
C5H0.026 (2)0.024 (2)0.017 (2)−0.0019 (16)0.0030 (15)−0.0001 (15)
C6H0.0206 (19)0.0195 (19)0.019 (2)−0.0006 (15)0.0022 (15)−0.0011 (15)
C7H0.036 (2)0.0172 (19)0.020 (2)−0.0011 (17)0.0038 (17)−0.0026 (15)
C8H0.026 (2)0.024 (2)0.017 (2)−0.0011 (16)0.0038 (15)−0.0037 (15)
C9H0.0169 (18)0.0203 (19)0.021 (2)0.0015 (14)−0.0010 (14)−0.0058 (15)
C10H0.0157 (18)0.0174 (19)0.029 (2)−0.0017 (14)0.0007 (15)−0.0062 (16)
C11H0.025 (2)0.028 (2)0.039 (3)0.0005 (18)0.0025 (19)0.007 (2)
O1I0.0305 (17)0.0222 (16)0.0217 (17)−0.0039 (12)0.0038 (13)0.0016 (12)
O2I0.0304 (17)0.0309 (17)0.0151 (15)−0.0009 (13)0.0061 (12)0.0012 (12)
O3I0.054 (2)0.0197 (16)0.0170 (16)0.0025 (14)0.0051 (14)0.0039 (12)
O4I0.053 (2)0.0204 (16)0.0222 (17)0.0065 (14)0.0012 (15)0.0009 (12)
N1I0.0218 (17)0.0178 (16)0.0155 (16)0.0002 (13)0.0022 (12)0.0035 (12)
N2I0.0187 (16)0.0168 (16)0.0181 (17)0.0014 (12)0.0021 (12)0.0002 (12)
C1I0.0170 (18)0.0170 (18)0.023 (2)0.0007 (14)0.0051 (15)0.0016 (14)
C2I0.0176 (18)0.0194 (19)0.019 (2)0.0010 (14)0.0048 (14)−0.0023 (14)
C3I0.0202 (19)0.023 (2)0.0147 (18)0.0011 (15)0.0039 (14)0.0012 (15)
C4I0.026 (2)0.0194 (19)0.0145 (18)0.0011 (15)0.0019 (14)0.0019 (14)
C5I0.031 (2)0.0182 (19)0.021 (2)0.0058 (16)0.0000 (16)−0.0032 (15)
C6I0.025 (2)0.025 (2)0.0143 (19)0.0044 (16)0.0005 (15)−0.0008 (15)
C7I0.032 (2)0.021 (2)0.020 (2)0.0041 (17)0.0032 (16)0.0032 (15)
C8I0.026 (2)0.021 (2)0.019 (2)−0.0027 (16)0.0043 (16)0.0040 (15)
C9I0.021 (2)0.022 (2)0.023 (2)0.0034 (15)0.0013 (15)0.0056 (15)
C10I0.022 (2)0.025 (2)0.024 (2)0.0057 (16)0.0068 (16)0.0062 (16)
C11I0.023 (2)0.033 (2)0.035 (3)−0.0002 (18)0.0035 (18)0.000 (2)
O1J0.0294 (16)0.0182 (14)0.0183 (15)−0.0017 (12)0.0059 (12)−0.0008 (11)
O2J0.0287 (16)0.0217 (15)0.0101 (14)0.0009 (12)0.0034 (11)0.0001 (11)
O3J0.0353 (17)0.0175 (14)0.0182 (15)0.0012 (12)0.0054 (12)0.0020 (11)
O4J0.0366 (18)0.0218 (15)0.0175 (15)−0.0005 (13)0.0038 (13)−0.0030 (11)
N1J0.0199 (16)0.0186 (16)0.0111 (15)−0.0005 (12)0.0022 (12)0.0032 (12)
N2J0.0119 (14)0.0232 (17)0.0109 (15)−0.0011 (12)0.0022 (11)0.0001 (12)
C1J0.0101 (15)0.0185 (17)0.0051 (15)0.0022 (12)−0.0007 (11)0.0037 (12)
C2J0.0161 (17)0.0169 (17)0.0056 (16)−0.0008 (13)0.0009 (12)0.0009 (12)
C3J0.0158 (17)0.0147 (17)0.0123 (18)0.0004 (13)0.0027 (13)0.0023 (13)
C4J0.0163 (17)0.0175 (18)0.0133 (18)0.0027 (13)0.0036 (13)0.0024 (13)
C5J0.0161 (17)0.0239 (19)0.0089 (17)0.0025 (14)0.0019 (13)0.0016 (14)
C6J0.0168 (17)0.0196 (18)0.0111 (17)0.0003 (14)0.0012 (13)0.0017 (13)
C7J0.0183 (18)0.0155 (17)0.0165 (19)0.0030 (14)0.0044 (14)0.0030 (13)
C8J0.025 (2)0.025 (2)0.0111 (18)−0.0002 (16)−0.0018 (14)0.0051 (14)
C9J0.0167 (18)0.024 (2)0.022 (2)−0.0012 (14)0.0038 (14)0.0061 (15)
C10J0.0171 (19)0.031 (2)0.026 (2)0.0026 (16)0.0030 (16)0.0115 (17)
C11J0.030 (2)0.037 (3)0.032 (3)0.004 (2)0.001 (2)−0.003 (2)
O1K0.0300 (17)0.0266 (16)0.0162 (15)0.0047 (13)−0.0005 (12)0.0001 (12)
O2K0.0327 (17)0.0300 (17)0.0114 (15)−0.0044 (13)0.0046 (12)0.0016 (12)
O3K0.0345 (18)0.0232 (16)0.0219 (17)−0.0031 (13)0.0055 (13)0.0038 (12)
O4K0.042 (2)0.0253 (17)0.0264 (18)0.0028 (14)0.0090 (15)0.0015 (13)
N1K0.0226 (17)0.0216 (17)0.0085 (15)0.0026 (13)0.0029 (12)0.0007 (12)
N2K0.0145 (15)0.0263 (17)0.0096 (15)−0.0001 (12)0.0015 (11)0.0004 (12)
C1K0.0101 (16)0.0221 (18)0.0120 (17)0.0011 (13)0.0024 (12)−0.0007 (13)
C2K0.0189 (18)0.0204 (18)0.0079 (16)0.0012 (14)0.0032 (13)−0.0011 (13)
C3K0.0130 (16)0.0219 (19)0.0107 (17)0.0014 (13)0.0029 (12)−0.0014 (13)
C4K0.0141 (17)0.0233 (19)0.0136 (18)0.0034 (14)0.0051 (13)0.0024 (14)
C5K0.0177 (18)0.0218 (19)0.0133 (18)0.0044 (14)0.0028 (13)0.0005 (14)
C6K0.0200 (18)0.0230 (19)0.0043 (15)0.0044 (14)0.0018 (12)−0.0013 (13)
C7K0.0149 (17)0.027 (2)0.0151 (18)0.0032 (15)0.0029 (13)−0.0005 (15)
C8K0.0227 (19)0.0211 (19)0.0104 (17)−0.0020 (15)0.0010 (14)0.0002 (13)
C9K0.0184 (18)0.026 (2)0.020 (2)0.0017 (15)0.0042 (14)0.0042 (15)
C10K0.020 (2)0.030 (2)0.028 (2)−0.0015 (17)0.0014 (17)0.0022 (18)
C11K0.034 (3)0.037 (3)0.032 (3)0.009 (2)−0.002 (2)−0.009 (2)
O1L0.0336 (17)0.0234 (16)0.0185 (16)0.0028 (13)0.0075 (13)−0.0003 (12)
O2L0.0363 (18)0.0284 (17)0.0184 (16)−0.0001 (14)0.0085 (13)0.0079 (13)
O4L0.0267 (16)0.0218 (15)0.0293 (18)−0.0030 (12)0.0075 (13)0.0026 (12)
O3L0.0333 (18)0.0280 (17)0.0223 (16)0.0010 (13)0.0066 (13)−0.0019 (12)
N1L0.0202 (17)0.0203 (17)0.0142 (16)0.0037 (13)0.0035 (12)0.0041 (12)
N2L0.0178 (16)0.0224 (17)0.0149 (17)0.0008 (13)0.0041 (12)0.0007 (13)
C1L0.0125 (16)0.0208 (19)0.0151 (18)0.0011 (13)0.0026 (13)0.0040 (14)
C2L0.0131 (17)0.025 (2)0.0119 (18)0.0004 (14)0.0028 (13)0.0033 (14)
C3L0.0146 (17)0.0169 (18)0.022 (2)−0.0002 (13)0.0054 (14)0.0041 (14)
C4L0.0115 (16)0.0207 (18)0.0164 (18)0.0009 (13)0.0044 (13)0.0032 (14)
C5L0.0124 (16)0.024 (2)0.0174 (19)−0.0019 (14)0.0027 (13)0.0027 (15)
C6L0.0191 (18)0.024 (2)0.0137 (19)−0.0004 (15)0.0029 (14)0.0042 (15)
C7L0.0131 (17)0.0213 (19)0.0216 (19)0.0002 (14)0.0054 (14)0.0009 (15)
C8L0.025 (2)0.022 (2)0.019 (2)0.0035 (16)0.0065 (15)0.0071 (15)
C9L0.035 (2)0.023 (2)0.032 (3)0.0109 (18)0.016 (2)0.0112 (18)
C10L0.029 (2)0.026 (2)0.042 (3)0.0001 (18)0.014 (2)−0.001 (2)
C11L0.042 (3)0.031 (3)0.045 (3)0.004 (2)0.009 (2)−0.002 (2)
Geometric parameters (Å, °) top
O1A—N2A1.249 (4)O1G—N2G1.247 (5)
O2A—N2A1.234 (4)O2G—N2G1.229 (5)
O3A—C7A1.311 (5)O4G—C7G1.253 (5)
O3A—H3AB0.82O3G—C7G1.301 (5)
O4A—C7A1.237 (5)O3G—H3GB0.82
N1A—C1A1.342 (5)N1G—C1G1.344 (6)
N1A—C8A1.457 (5)N1G—C8G1.477 (6)
N1A—H1AA0.86N1G—H1GA0.86
N2A—C2A1.439 (5)N2G—C2G1.450 (5)
C1A—C6A1.410 (6)C1G—C6G1.427 (6)
C1A—C2A1.446 (5)C1G—C2G1.439 (6)
C2A—C3A1.393 (5)C2G—C3G1.396 (6)
C3A—C4A1.382 (5)C3G—C4G1.380 (6)
C3A—H3AA0.93C3G—H3GA0.93
C4A—C5A1.409 (5)C4G—C5G1.409 (6)
C4A—C7A1.481 (5)C4G—C7G1.476 (6)
C5A—C6A1.374 (5)C5G—C6G1.359 (6)
C5A—H5AA0.93C5G—H5GA0.93
C6A—H6AA0.93C6G—H6GA0.93
C8A—C9A1.534 (6)C8G—C9G1.532 (8)
C8A—H8AA0.97C8G—H8GA0.97
C8A—H8AB0.97C8G—H8GB0.97
C9A—C10A1.472 (6)C9G—C10G1.424 (11)
C9A—H9AA0.97C9G—H9GA0.97
C9A—H9AB0.97C9G—H9GB0.97
C10A—C11A1.322 (7)C10G—C11G1.350 (9)
C10A—H10A0.93C10G—H10G0.93
C11A—H11A0.93C11G—H11M0.93
C11A—H11B0.93C11G—H11N0.93
O1B—N2B1.240 (5)O1H—N2H1.239 (5)
O2B—N2B1.225 (5)O2H—N2H1.235 (5)
O3B—C7B1.310 (6)O3H—C7H1.312 (5)
O3B—H3BB0.82O3H—H3HB0.82
O4B—C7B1.244 (6)O4H—C7H1.251 (5)
N1B—C1B1.343 (6)N1H—C1H1.347 (5)
N1B—C8B1.460 (6)N1H—C8H1.456 (6)
N1B—H1BA0.86N1H—H1HA0.86
N2B—C2B1.440 (6)N2H—C2H1.452 (5)
C1B—C6B1.411 (7)C1H—C2H1.429 (6)
C1B—C2B1.431 (6)C1H—C6H1.432 (6)
C2B—C3B1.382 (6)C2H—C3H1.389 (6)
C3B—C4B1.385 (6)C3H—C4H1.381 (6)
C3B—H3BA0.93C3H—H3HA0.93
C4B—C5B1.411 (6)C4H—C5H1.409 (6)
C4B—C7B1.480 (7)C4H—C7H1.478 (6)
C5B—C6B1.374 (7)C5H—C6H1.376 (6)
C5B—H5BA0.93C5H—H5HA0.93
C6B—H6BA0.93C6H—H6HA0.93
C8B—C9B1.504 (7)C8H—C9H1.534 (6)
C8B—H8BA0.97C8H—H8HA0.97
C8B—H8BB0.97C8H—H8HB0.97
C9B—C10B1.511 (7)C9H—C10H1.497 (6)
C9B—H9BA0.97C9H—H9HA0.97
C9B—H9BB0.97C9H—H9HB0.97
C10B—C11B1.307 (8)C10H—C11H1.321 (7)
C10B—H10B0.93C10H—H10H0.93
C11B—H11C0.93C11H—H11O0.93
C11B—H11D0.93C11H—H11P0.93
O1C—N2C1.249 (5)O1I—N2I1.242 (5)
O2C—N2C1.228 (5)O2I—N2I1.245 (5)
O3C—C7C1.322 (5)O3I—C7I1.319 (5)
O3C—H3CB0.82O3I—H3IB0.82
O4C—C7C1.236 (5)O4I—C7I1.242 (6)
N1C—C1C1.350 (6)N1I—C1I1.345 (5)
N1C—C8C1.470 (6)N1I—C8I1.455 (6)
N1C—H1CA0.86N1I—H1IA0.86
N2C—C2C1.459 (5)N2I—C2I1.442 (5)
C1C—C6C1.416 (6)C1I—C2I1.416 (6)
C1C—C2C1.429 (6)C1I—C6I1.427 (6)
C2C—C3C1.385 (6)C2I—C3I1.399 (6)
C3C—C4C1.386 (6)C3I—C4I1.384 (6)
C3C—H3CA0.93C3I—H3IA0.93
C4C—C5C1.414 (6)C4I—C5I1.406 (6)
C4C—C7C1.464 (6)C4I—C7I1.477 (6)
C5C—C6C1.364 (6)C5I—C6I1.377 (6)
C5C—H5CA0.93C5I—H5IA0.93
C6C—H6CA0.93C6I—H6IA0.93
C8C—C9C1.529 (6)C8I—C9I1.536 (6)
C8C—H8CA0.97C8I—H8IA0.97
C8C—H8CB0.97C8I—H8IB0.97
C9C—C10C1.501 (7)C9I—C10I1.484 (6)
C9C—H9CA0.97C9I—H9IA0.97
C9C—H9CB0.97C9I—H9IB0.97
C10C—C11C1.320 (7)C10I—C11I1.340 (7)
C10C—H10C0.93C10I—H10I0.93
C11C—H11E0.93C11I—H11Q0.93
C11C—H11F0.93C11I—H11R0.93
O1D—N2D1.256 (5)O1J—N2J1.243 (5)
O2D—N2D1.229 (5)O2J—N2J1.242 (4)
O3D—C7D1.305 (5)O3J—C7J1.308 (5)
O3D—H3DB0.82O3J—H3JB0.82
O4D—C7D1.233 (5)O4J—C7J1.235 (5)
N1D—C1D1.346 (5)N1J—C1J1.336 (5)
N1D—C8D1.464 (6)N1J—C8J1.458 (5)
N1D—H1DA0.86N1J—H1JA0.86
N2D—C2D1.454 (5)N2J—C2J1.422 (5)
C1D—C2D1.424 (6)C1J—C6J1.426 (6)
C1D—C6D1.430 (6)C1J—C2J1.445 (5)
C2D—C3D1.404 (6)C2J—C3J1.396 (5)
C3D—C4D1.383 (6)C3J—C4J1.382 (6)
C3D—H3DA0.93C3J—H3JA0.93
C4D—C5D1.411 (6)C4J—C5J1.415 (5)
C4D—C7D1.468 (6)C4J—C7J1.474 (5)
C5D—C6D1.365 (6)C5J—C6J1.367 (6)
C5D—H5DA0.93C5J—H5JA0.93
C6D—H6DA0.93C6J—H6JA0.93
C8D—C9D1.541 (8)C8J—C9J1.530 (6)
C8D—H8DA0.97C8J—H8JA0.97
C8D—H8DB0.97C8J—H8JB0.97
C9D—C10D1.482 (8)C9J—C10J1.490 (6)
C9D—H9DA0.97C9J—H9JA0.97
C9D—H9DB0.97C9J—H9JB0.97
C10D—C11D1.326 (8)C10J—C11J1.311 (7)
C10D—H10D0.93C10J—H10J0.93
C11D—H11G0.93C11J—H11S0.93
C11D—H11H0.93C11J—H11T0.93
O1E—N2E1.247 (5)O1K—N2K1.246 (5)
O2E—N2E1.238 (5)O2K—N2K1.241 (5)
O3E—C7E1.310 (5)O3K—C7K1.295 (5)
O3E—H3EB0.82O3K—H3KB0.82
O4E—C7E1.253 (5)O4K—C7K1.252 (5)
N1E—C1E1.350 (6)N1K—C1K1.335 (5)
N1E—C8E1.455 (6)N1K—C8K1.470 (5)
N1E—H1EA0.86N1K—H1KA0.86
N2E—C2E1.452 (6)N2K—C2K1.439 (5)
C1E—C6E1.428 (6)C1K—C6K1.418 (5)
C1E—C2E1.435 (6)C1K—C2K1.437 (5)
C2E—C3E1.383 (6)C2K—C3K1.395 (6)
C3E—C4E1.386 (6)C3K—C4K1.377 (6)
C3E—H3EA0.93C3K—H3KA0.93
C4E—C5E1.430 (6)C4K—C5K1.415 (6)
C4E—C7E1.483 (6)C4K—C7K1.468 (6)
C5E—C6E1.371 (6)C5K—C6K1.368 (6)
C5E—H5EA0.93C5K—H5KA0.93
C6E—H6EA0.93C6K—H6KA0.93
C8E—C9E1.537 (7)C8K—C9K1.531 (6)
C8E—H8EA0.97C8K—H8KA0.97
C8E—H8EB0.97C8K—H8KB0.97
C9E—C10E1.491 (8)C9K—C10K1.491 (6)
C9E—H9EA0.97C9K—H9KA0.97
C9E—H9EB0.97C9K—H9KB0.97
C10E—C11E1.323 (8)C10K—C11K1.322 (7)
C10E—H10E0.93C10K—H10K0.93
C11E—H11I0.93C11K—H11U0.93
C11E—H11J0.93C11K—H11V0.93
O1F—N2F1.246 (5)O1L—N2L1.247 (5)
O2F—N2F1.234 (5)O2L—N2L1.245 (5)
O3F—C7F1.298 (5)O4L—C7L1.253 (5)
O3F—H3FB0.82O3L—C7L1.289 (5)
O4F—C7F1.244 (5)O3L—H3LB0.82
N1F—C1F1.344 (5)N1L—C1L1.340 (5)
N1F—C8F1.460 (5)N1L—C8L1.461 (5)
N1F—H1FA0.86N1L—H1LA0.86
N2F—C2F1.459 (6)N2L—C2L1.441 (5)
C1F—C2F1.424 (6)C1L—C6L1.423 (6)
C1F—C6F1.433 (6)C1L—C2L1.432 (6)
C2F—C3F1.391 (6)C2L—C3L1.397 (6)
C3F—C4F1.382 (6)C3L—C4L1.386 (6)
C3F—H3FA0.93C3L—H3LA0.93
C4F—C5F1.406 (6)C4L—C5L1.407 (6)
C4F—C7F1.470 (6)C4L—C7L1.468 (6)
C5F—C6F1.367 (6)C5L—C6L1.363 (6)
C5F—H5FA0.93C5L—H5LA0.93
C6F—H6FA0.93C6L—H6LA0.93
C8F—C9F1.527 (6)C8L—C9L1.518 (7)
C8F—H8FA0.97C8L—H8LA0.97
C8F—H8FB0.97C8L—H8LB0.97
C9F—C10F1.496 (6)C9L—C10L1.487 (8)
C9F—H9FA0.97C9L—H9LA0.97
C9F—H9FB0.97C9L—H9LB0.97
C10F—C11F1.319 (7)C10L—C11L1.308 (8)
C10F—H10F0.93C10L—H10L0.93
C11F—H11K0.93C11L—H11W0.93
C11F—H11L0.93C11L—H11X0.93
C7A—O3A—H3AB109.5C7G—O3G—H3GB109.5
C1A—N1A—C8A123.5 (3)C1G—N1G—C8G122.6 (4)
C1A—N1A—H1AA118.2C1G—N1G—H1GA118.7
C8A—N1A—H1AA118.2C8G—N1G—H1GA118.7
O2A—N2A—O1A121.1 (3)O2G—N2G—O1G122.7 (4)
O2A—N2A—C2A119.3 (3)O2G—N2G—C2G119.1 (4)
O1A—N2A—C2A119.6 (3)O1G—N2G—C2G118.3 (4)
N1A—C1A—C6A120.7 (4)N1G—C1G—C6G120.5 (4)
N1A—C1A—C2A123.9 (4)N1G—C1G—C2G123.7 (4)
C6A—C1A—C2A115.4 (3)C6G—C1G—C2G115.8 (4)
C3A—C2A—N2A116.7 (3)C3G—C2G—C1G121.5 (4)
C3A—C2A—C1A121.6 (4)C3G—C2G—N2G116.5 (4)
N2A—C2A—C1A121.7 (3)C1G—C2G—N2G122.1 (4)
C4A—C3A—C2A120.3 (3)C4G—C3G—C2G120.0 (4)
C4A—C3A—H3AA119.9C4G—C3G—H3GA120.0
C2A—C3A—H3AA119.9C2G—C3G—H3GA120.0
C3A—C4A—C5A119.7 (3)C3G—C4G—C5G119.9 (4)
C3A—C4A—C7A119.8 (3)C3G—C4G—C7G119.5 (4)
C5A—C4A—C7A120.5 (3)C5G—C4G—C7G120.5 (4)
C6A—C5A—C4A120.0 (4)C6G—C5G—C4G120.6 (4)
C6A—C5A—H5AA120.0C6G—C5G—H5GA119.7
C4A—C5A—H5AA120.0C4G—C5G—H5GA119.7
C5A—C6A—C1A123.0 (4)C5G—C6G—C1G122.2 (4)
C5A—C6A—H6AA118.5C5G—C6G—H6GA118.9
C1A—C6A—H6AA118.5C1G—C6G—H6GA118.9
O4A—C7A—O3A124.5 (4)O4G—C7G—O3G123.1 (4)
O4A—C7A—C4A121.7 (4)O4G—C7G—C4G121.8 (4)
O3A—C7A—C4A113.8 (3)O3G—C7G—C4G115.0 (4)
N1A—C8A—C9A109.4 (3)N1G—C8G—C9G108.9 (4)
N1A—C8A—H8AA109.8N1G—C8G—H8GA109.9
C9A—C8A—H8AA109.8C9G—C8G—H8GA109.9
N1A—C8A—H8AB109.8N1G—C8G—H8GB109.9
C9A—C8A—H8AB109.8C9G—C8G—H8GB109.9
H8AA—C8A—H8AB108.2H8GA—C8G—H8GB108.3
C10A—C9A—C8A112.5 (4)C10G—C9G—C8G112.6 (6)
C10A—C9A—H9AA109.1C10G—C9G—H9GA109.1
C8A—C9A—H9AA109.1C8G—C9G—H9GA109.1
C10A—C9A—H9AB109.1C10G—C9G—H9GB109.1
C8A—C9A—H9AB109.1C8G—C9G—H9GB109.1
H9AA—C9A—H9AB107.8H9GA—C9G—H9GB107.8
C11A—C10A—C9A126.4 (5)C11G—C10G—C9G122.8 (8)
C11A—C10A—H10A116.8C11G—C10G—H10G118.6
C9A—C10A—H10A116.8C9G—C10G—H10G118.6
C10A—C11A—H11A120.0C10G—C11G—H11M120.0
C10A—C11A—H11B120.0C10G—C11G—H11N120.0
H11A—C11A—H11B120.0H11M—C11G—H11N120.0
C7B—O3B—H3BB109.5C7H—O3H—H3HB109.5
C1B—N1B—C8B124.7 (4)C1H—N1H—C8H124.9 (4)
C1B—N1B—H1BA117.7C1H—N1H—H1HA117.6
C8B—N1B—H1BA117.7C8H—N1H—H1HA117.6
O2B—N2B—O1B121.4 (4)O2H—N2H—O1H122.2 (4)
O2B—N2B—C2B119.9 (4)O2H—N2H—C2H118.9 (4)
O1B—N2B—C2B118.7 (4)O1H—N2H—C2H118.9 (4)
N1B—C1B—C6B119.8 (4)N1H—C1H—C2H124.3 (4)
N1B—C1B—C2B124.1 (4)N1H—C1H—C6H119.9 (4)
C6B—C1B—C2B116.2 (4)C2H—C1H—C6H115.8 (4)
C3B—C2B—C1B122.0 (4)C3H—C2H—C1H122.1 (4)
C3B—C2B—N2B116.1 (4)C3H—C2H—N2H116.6 (4)
C1B—C2B—N2B121.9 (4)C1H—C2H—N2H121.3 (4)
C2B—C3B—C4B120.1 (4)C4H—C3H—C2H120.2 (4)
C2B—C3B—H3BA119.9C4H—C3H—H3HA119.9
C4B—C3B—H3BA119.9C2H—C3H—H3HA119.9
C3B—C4B—C5B119.2 (4)C3H—C4H—C5H119.7 (4)
C3B—C4B—C7B121.1 (4)C3H—C4H—C7H120.7 (4)
C5B—C4B—C7B119.6 (4)C5H—C4H—C7H119.5 (4)
C6B—C5B—C4B120.7 (4)C6H—C5H—C4H120.5 (4)
C6B—C5B—H5BA119.7C6H—C5H—H5HA119.8
C4B—C5B—H5BA119.7C4H—C5H—H5HA119.8
C5B—C6B—C1B121.8 (4)C5H—C6H—C1H121.7 (4)
C5B—C6B—H6BA119.1C5H—C6H—H6HA119.2
C1B—C6B—H6BA119.1C1H—C6H—H6HA119.2
O4B—C7B—O3B123.6 (4)O4H—C7H—O3H123.4 (4)
O4B—C7B—C4B120.2 (4)O4H—C7H—C4H120.2 (4)
O3B—C7B—C4B116.2 (4)O3H—C7H—C4H116.5 (4)
N1B—C8B—C9B109.4 (4)N1H—C8H—C9H108.6 (4)
N1B—C8B—H8BA109.8N1H—C8H—H8HA110.0
C9B—C8B—H8BA109.8C9H—C8H—H8HA110.0
N1B—C8B—H8BB109.8N1H—C8H—H8HB110.0
C9B—C8B—H8BB109.8C9H—C8H—H8HB110.0
H8BA—C8B—H8BB108.2H8HA—C8H—H8HB108.4
C8B—C9B—C10B111.2 (4)C10H—C9H—C8H111.6 (3)
C8B—C9B—H9BA109.4C10H—C9H—H9HA109.3
C10B—C9B—H9BA109.4C8H—C9H—H9HA109.3
C8B—C9B—H9BB109.4C10H—C9H—H9HB109.3
C10B—C9B—H9BB109.4C8H—C9H—H9HB109.3
H9BA—C9B—H9BB108.0H9HA—C9H—H9HB108.0
C11B—C10B—C9B124.1 (5)C11H—C10H—C9H124.4 (4)
C11B—C10B—H10B118.0C11H—C10H—H10H117.8
C9B—C10B—H10B118.0C9H—C10H—H10H117.8
C10B—C11B—H11C120.0C10H—C11H—H11O120.0
C10B—C11B—H11D120.0C10H—C11H—H11P120.0
H11C—C11B—H11D120.0H11O—C11H—H11P120.0
C7C—O3C—H3CB109.5C7I—O3I—H3IB109.5
C1C—N1C—C8C124.6 (4)C1I—N1I—C8I124.6 (4)
C1C—N1C—H1CA117.7C1I—N1I—H1IA117.7
C8C—N1C—H1CA117.7C8I—N1I—H1IA117.7
O2C—N2C—O1C122.3 (4)O1I—N2I—O2I122.0 (4)
O2C—N2C—C2C118.4 (4)O1I—N2I—C2I118.9 (4)
O1C—N2C—C2C119.3 (4)O2I—N2I—C2I119.0 (4)
N1C—C1C—C6C120.8 (4)N1I—C1I—C2I124.1 (4)
N1C—C1C—C2C123.3 (4)N1I—C1I—C6I119.3 (4)
C6C—C1C—C2C115.8 (4)C2I—C1I—C6I116.6 (4)
C3C—C2C—C1C121.7 (4)C3I—C2I—C1I122.0 (4)
C3C—C2C—N2C116.6 (4)C3I—C2I—N2I116.1 (4)
C1C—C2C—N2C121.6 (4)C1I—C2I—N2I121.9 (4)
C2C—C3C—C4C121.0 (4)C4I—C3I—C2I120.2 (4)
C2C—C3C—H3CA119.5C4I—C3I—H3IA119.9
C4C—C3C—H3CA119.5C2I—C3I—H3IA119.9
C3C—C4C—C5C118.0 (4)C3I—C4I—C5I118.9 (4)
C3C—C4C—C7C122.2 (4)C3I—C4I—C7I121.4 (4)
C5C—C4C—C7C119.8 (4)C5I—C4I—C7I119.7 (4)
C6C—C5C—C4C121.5 (4)C6I—C5I—C4I121.6 (4)
C6C—C5C—H5CA119.3C6I—C5I—H5IA119.2
C4C—C5C—H5CA119.3C4I—C5I—H5IA119.2
C5C—C6C—C1C121.9 (4)C5I—C6I—C1I120.8 (4)
C5C—C6C—H6CA119.0C5I—C6I—H6IA119.6
C1C—C6C—H6CA119.0C1I—C6I—H6IA119.6
O4C—C7C—O3C123.3 (4)O4I—C7I—O3I122.9 (4)
O4C—C7C—C4C121.3 (4)O4I—C7I—C4I121.4 (4)
O3C—C7C—C4C115.4 (4)O3I—C7I—C4I115.7 (4)
N1C—C8C—C9C108.6 (4)N1I—C8I—C9I109.3 (4)
N1C—C8C—H8CA110.0N1I—C8I—H8IA109.8
C9C—C8C—H8CA110.0C9I—C8I—H8IA109.8
N1C—C8C—H8CB110.0N1I—C8I—H8IB109.8
C9C—C8C—H8CB110.0C9I—C8I—H8IB109.8
H8CA—C8C—H8CB108.4H8IA—C8I—H8IB108.3
C10C—C9C—C8C112.4 (4)C10I—C9I—C8I111.8 (4)
C10C—C9C—H9CA109.1C10I—C9I—H9IA109.3
C8C—C9C—H9CA109.1C8I—C9I—H9IA109.3
C10C—C9C—H9CB109.1C10I—C9I—H9IB109.3
C8C—C9C—H9CB109.1C8I—C9I—H9IB109.3
H9CA—C9C—H9CB107.8H9IA—C9I—H9IB107.9
C11C—C10C—C9C124.9 (5)C11I—C10I—C9I125.1 (4)
C11C—C10C—H10C117.6C11I—C10I—H10I117.4
C9C—C10C—H10C117.6C9I—C10I—H10I117.4
C10C—C11C—H11E120.0C10I—C11I—H11Q120.0
C10C—C11C—H11F120.0C10I—C11I—H11R120.0
H11E—C11C—H11F120.0H11Q—C11I—H11R120.0
C7D—O3D—H3DB109.5C7J—O3J—H3JB109.5
C1D—N1D—C8D124.5 (4)C1J—N1J—C8J124.3 (4)
C1D—N1D—H1DA117.8C1J—N1J—H1JA117.8
C8D—N1D—H1DA117.8C8J—N1J—H1JA117.8
O2D—N2D—O1D123.1 (4)O2J—N2J—O1J121.2 (3)
O2D—N2D—C2D119.2 (4)O2J—N2J—C2J119.3 (3)
O1D—N2D—C2D117.7 (3)O1J—N2J—C2J119.5 (3)
N1D—C1D—C2D124.9 (4)N1J—C1J—C6J120.7 (3)
N1D—C1D—C6D119.2 (4)N1J—C1J—C2J123.7 (4)
C2D—C1D—C6D115.9 (4)C6J—C1J—C2J115.6 (3)
C3D—C2D—C1D122.3 (4)C3J—C2J—N2J117.2 (3)
C3D—C2D—N2D115.5 (4)C3J—C2J—C1J121.4 (4)
C1D—C2D—N2D122.1 (4)N2J—C2J—C1J121.4 (3)
C4D—C3D—C2D119.8 (4)C4J—C3J—C2J120.8 (4)
C4D—C3D—H3DA120.1C4J—C3J—H3JA119.6
C2D—C3D—H3DA120.1C2J—C3J—H3JA119.6
C3D—C4D—C5D118.8 (4)C3J—C4J—C5J119.0 (4)
C3D—C4D—C7D119.9 (4)C3J—C4J—C7J121.5 (4)
C5D—C4D—C7D121.2 (4)C5J—C4J—C7J119.4 (4)
C6D—C5D—C4D122.0 (4)C6J—C5J—C4J120.9 (4)
C6D—C5D—H5DA119.0C6J—C5J—H5JA119.5
C4D—C5D—H5DA119.0C4J—C5J—H5JA119.5
C5D—C6D—C1D121.1 (4)C5J—C6J—C1J122.3 (4)
C5D—C6D—H6DA119.4C5J—C6J—H6JA118.9
C1D—C6D—H6DA119.4C1J—C6J—H6JA118.9
O4D—C7D—O3D123.5 (4)O4J—C7J—O3J123.5 (4)
O4D—C7D—C4D122.1 (4)O4J—C7J—C4J120.7 (4)
O3D—C7D—C4D114.3 (4)O3J—C7J—C4J115.7 (4)
N1D—C8D—C9D108.9 (4)N1J—C8J—C9J108.7 (4)
N1D—C8D—H8DA109.9N1J—C8J—H8JA109.9
C9D—C8D—H8DA109.9C9J—C8J—H8JA109.9
N1D—C8D—H8DB109.9N1J—C8J—H8JB109.9
C9D—C8D—H8DB109.9C9J—C8J—H8JB109.9
H8DA—C8D—H8DB108.3H8JA—C8J—H8JB108.3
C10D—C9D—C8D110.1 (5)C10J—C9J—C8J112.4 (4)
C10D—C9D—H9DA109.6C10J—C9J—H9JA109.1
C8D—C9D—H9DA109.6C8J—C9J—H9JA109.1
C10D—C9D—H9DB109.6C10J—C9J—H9JB109.1
C8D—C9D—H9DB109.6C8J—C9J—H9JB109.1
H9DA—C9D—H9DB108.2H9JA—C9J—H9JB107.9
C11D—C10D—C9D123.8 (6)C11J—C10J—C9J126.5 (4)
C11D—C10D—H10D118.1C11J—C10J—H10J116.8
C9D—C10D—H10D118.1C9J—C10J—H10J116.8
C10D—C11D—H11G120.0C10J—C11J—H11S120.0
C10D—C11D—H11H120.0C10J—C11J—H11T120.0
H11G—C11D—H11H120.0H11S—C11J—H11T120.0
C7E—O3E—H3EB109.5C7K—O3K—H3KB109.5
C1E—N1E—C8E122.8 (4)C1K—N1K—C8K124.7 (4)
C1E—N1E—H1EA118.6C1K—N1K—H1KA117.6
C8E—N1E—H1EA118.6C8K—N1K—H1KA117.6
O2E—N2E—O1E122.2 (4)O2K—N2K—O1K121.5 (4)
O2E—N2E—C2E118.8 (4)O2K—N2K—C2K119.2 (4)
O1E—N2E—C2E119.0 (4)O1K—N2K—C2K119.3 (3)
N1E—C1E—C6E119.3 (4)N1K—C1K—C6K121.0 (4)
N1E—C1E—C2E125.0 (4)N1K—C1K—C2K123.3 (4)
C6E—C1E—C2E115.8 (4)C6K—C1K—C2K115.7 (4)
C3E—C2E—C1E122.0 (4)C3K—C2K—C1K121.5 (4)
C3E—C2E—N2E116.9 (4)C3K—C2K—N2K116.8 (3)
C1E—C2E—N2E121.1 (4)C1K—C2K—N2K121.6 (4)
C2E—C3E—C4E121.0 (4)C4K—C3K—C2K121.0 (4)
C2E—C3E—H3EA119.5C4K—C3K—H3KA119.5
C4E—C3E—H3EA119.5C2K—C3K—H3KA119.5
C3E—C4E—C5E118.6 (4)C3K—C4K—C5K118.4 (4)
C3E—C4E—C7E121.0 (4)C3K—C4K—C7K121.5 (4)
C5E—C4E—C7E120.4 (4)C5K—C4K—C7K120.1 (4)
C6E—C5E—C4E120.6 (4)C6K—C5K—C4K121.3 (4)
C6E—C5E—H5EA119.7C6K—C5K—H5KA119.4
C4E—C5E—H5EA119.7C4K—C5K—H5KA119.4
C5E—C6E—C1E122.1 (4)C5K—C6K—C1K122.0 (4)
C5E—C6E—H6EA119.0C5K—C6K—H6KA119.0
C1E—C6E—H6EA119.0C1K—C6K—H6KA119.0
O4E—C7E—O3E122.8 (4)O4K—C7K—O3K123.6 (4)
O4E—C7E—C4E122.1 (4)O4K—C7K—C4K120.0 (4)
O3E—C7E—C4E115.1 (4)O3K—C7K—C4K116.4 (4)
N1E—C8E—C9E109.8 (4)N1K—C8K—C9K108.9 (3)
N1E—C8E—H8EA109.7N1K—C8K—H8KA109.9
C9E—C8E—H8EA109.7C9K—C8K—H8KA109.9
N1E—C8E—H8EB109.7N1K—C8K—H8KB109.9
C9E—C8E—H8EB109.7C9K—C8K—H8KB109.9
H8EA—C8E—H8EB108.2H8KA—C8K—H8KB108.3
C10E—C9E—C8E114.1 (4)C10K—C9K—C8K111.8 (4)
C10E—C9E—H9EA108.7C10K—C9K—H9KA109.3
C8E—C9E—H9EA108.7C8K—C9K—H9KA109.3
C10E—C9E—H9EB108.7C10K—C9K—H9KB109.3
C8E—C9E—H9EB108.7C8K—C9K—H9KB109.3
H9EA—C9E—H9EB107.6H9KA—C9K—H9KB107.9
C11E—C10E—C9E123.1 (5)C11K—C10K—C9K124.5 (5)
C11E—C10E—H10E118.4C11K—C10K—H10K117.8
C9E—C10E—H10E118.4C9K—C10K—H10K117.8
C10E—C11E—H11I120.0C10K—C11K—H11U120.0
C10E—C11E—H11J120.0C10K—C11K—H11V120.0
H11I—C11E—H11J120.0H11U—C11K—H11V120.0
C7F—O3F—H3FB109.5C7L—O3L—H3LB109.5
C1F—N1F—C8F124.2 (4)C1L—N1L—C8L123.4 (4)
C1F—N1F—H1FA117.9C1L—N1L—H1LA118.3
C8F—N1F—H1FA117.9C8L—N1L—H1LA118.3
O2F—N2F—O1F121.7 (4)O1L—N2L—O2L120.9 (4)
O2F—N2F—C2F119.7 (4)O1L—N2L—C2L119.9 (4)
O1F—N2F—C2F118.6 (4)O2L—N2L—C2L119.2 (4)
N1F—C1F—C2F124.6 (4)N1L—C1L—C6L119.6 (4)
N1F—C1F—C6F119.3 (4)N1L—C1L—C2L124.9 (4)
C2F—C1F—C6F116.1 (4)C6L—C1L—C2L115.5 (4)
C3F—C2F—C1F122.1 (4)C3L—C2L—C1L122.0 (4)
C3F—C2F—N2F116.1 (4)C3L—C2L—N2L116.9 (4)
C1F—C2F—N2F121.8 (4)C1L—C2L—N2L121.1 (4)
C4F—C3F—C2F120.3 (4)C4L—C3L—C2L120.2 (4)
C4F—C3F—H3FA119.8C4L—C3L—H3LA119.9
C2F—C3F—H3FA119.8C2L—C3L—H3LA119.9
C3F—C4F—C5F118.6 (4)C3L—C4L—C5L118.8 (4)
C3F—C4F—C7F120.6 (4)C3L—C4L—C7L120.5 (4)
C5F—C4F—C7F120.8 (4)C5L—C4L—C7L120.7 (4)
C6F—C5F—C4F122.2 (4)C6L—C5L—C4L121.4 (4)
C6F—C5F—H5FA118.9C6L—C5L—H5LA119.3
C4F—C5F—H5FA118.9C4L—C5L—H5LA119.3
C5F—C6F—C1F120.6 (4)C5L—C6L—C1L122.0 (4)
C5F—C6F—H6FA119.7C5L—C6L—H6LA119.0
C1F—C6F—H6FA119.7C1L—C6L—H6LA119.0
O4F—C7F—O3F123.2 (4)O4L—C7L—O3L123.6 (4)
O4F—C7F—C4F121.4 (4)O4L—C7L—C4L120.8 (4)
O3F—C7F—C4F115.4 (4)O3L—C7L—C4L115.5 (4)
N1F—C8F—C9F109.3 (3)N1L—C8L—C9L110.4 (4)
N1F—C8F—H8FA109.8N1L—C8L—H8LA109.6
C9F—C8F—H8FA109.8C9L—C8L—H8LA109.6
N1F—C8F—H8FB109.8N1L—C8L—H8LB109.6
C9F—C8F—H8FB109.8C9L—C8L—H8LB109.6
H8FA—C8F—H8FB108.3H8LA—C8L—H8LB108.1
C10F—C9F—C8F112.1 (4)C10L—C9L—C8L113.7 (4)
C10F—C9F—H9FA109.2C10L—C9L—H9LA108.8
C8F—C9F—H9FA109.2C8L—C9L—H9LA108.8
C10F—C9F—H9FB109.2C10L—C9L—H9LB108.8
C8F—C9F—H9FB109.2C8L—C9L—H9LB108.8
H9FA—C9F—H9FB107.9H9LA—C9L—H9LB107.7
C11F—C10F—C9F125.0 (4)C11L—C10L—C9L125.1 (5)
C11F—C10F—H10F117.5C11L—C10L—H10L117.4
C9F—C10F—H10F117.5C9L—C10L—H10L117.4
C10F—C11F—H11K120.0C10L—C11L—H11W120.0
C10F—C11F—H11L120.0C10L—C11L—H11X120.0
H11K—C11F—H11L120.0H11W—C11L—H11X120.0
C8A—N1A—C1A—C6A2.2 (6)C8G—N1G—C1G—C6G−0.2 (7)
C8A—N1A—C1A—C2A−176.0 (4)C8G—N1G—C1G—C2G178.6 (4)
O2A—N2A—C2A—C3A−6.8 (5)N1G—C1G—C2G—C3G−178.8 (4)
O1A—N2A—C2A—C3A174.4 (3)C6G—C1G—C2G—C3G0.0 (6)
O2A—N2A—C2A—C1A175.6 (3)N1G—C1G—C2G—N2G0.3 (7)
O1A—N2A—C2A—C1A−3.2 (5)C6G—C1G—C2G—N2G179.1 (4)
N1A—C1A—C2A—C3A179.7 (4)O2G—N2G—C2G—C3G1.5 (6)
C6A—C1A—C2A—C3A1.4 (5)O1G—N2G—C2G—C3G−179.9 (4)
N1A—C1A—C2A—N2A−2.9 (6)O2G—N2G—C2G—C1G−177.7 (4)
C6A—C1A—C2A—N2A178.8 (3)O1G—N2G—C2G—C1G1.0 (6)
N2A—C2A—C3A—C4A−178.7 (3)C1G—C2G—C3G—C4G0.3 (6)
C1A—C2A—C3A—C4A−1.2 (6)N2G—C2G—C3G—C4G−178.9 (4)
C2A—C3A—C4A—C5A1.0 (6)C2G—C3G—C4G—C5G−0.4 (6)
C2A—C3A—C4A—C7A179.7 (3)C2G—C3G—C4G—C7G179.7 (4)
C3A—C4A—C5A—C6A−1.1 (6)C3G—C4G—C5G—C6G0.1 (6)
C7A—C4A—C5A—C6A−179.8 (4)C7G—C4G—C5G—C6G−180.0 (4)
C4A—C5A—C6A—C1A1.4 (6)C4G—C5G—C6G—C1G0.2 (7)
N1A—C1A—C6A—C5A−179.9 (4)N1G—C1G—C6G—C5G178.6 (4)
C2A—C1A—C6A—C5A−1.5 (6)C2G—C1G—C6G—C5G−0.3 (6)
C3A—C4A—C7A—O4A−0.7 (6)C3G—C4G—C7G—O4G−0.8 (6)
C5A—C4A—C7A—O4A178.0 (4)C5G—C4G—C7G—O4G179.3 (4)
C3A—C4A—C7A—O3A179.1 (3)C3G—C4G—C7G—O3G179.4 (4)
C5A—C4A—C7A—O3A−2.2 (5)C5G—C4G—C7G—O3G−0.6 (6)
C1A—N1A—C8A—C9A165.6 (4)C1G—N1G—C8G—C9G−172.8 (5)
N1A—C8A—C9A—C10A65.8 (5)N1G—C8G—C9G—C10G−59.6 (7)
C8A—C9A—C10A—C11A−121.7 (5)C8G—C9G—C10G—C11G126.6 (7)
C8B—N1B—C1B—C6B7.5 (7)C8H—N1H—C1H—C2H−178.6 (4)
C8B—N1B—C1B—C2B−171.8 (4)C8H—N1H—C1H—C6H1.3 (6)
N1B—C1B—C2B—C3B176.1 (4)N1H—C1H—C2H—C3H177.2 (4)
C6B—C1B—C2B—C3B−3.2 (6)C6H—C1H—C2H—C3H−2.7 (6)
N1B—C1B—C2B—N2B−0.9 (7)N1H—C1H—C2H—N2H0.0 (6)
C6B—C1B—C2B—N2B179.8 (4)C6H—C1H—C2H—N2H−179.9 (3)
O2B—N2B—C2B—C3B−4.7 (6)O2H—N2H—C2H—C3H1.1 (6)
O1B—N2B—C2B—C3B176.2 (4)O1H—N2H—C2H—C3H−179.6 (4)
O2B—N2B—C2B—C1B172.5 (4)O2H—N2H—C2H—C1H178.5 (4)
O1B—N2B—C2B—C1B−6.6 (6)O1H—N2H—C2H—C1H−2.3 (6)
C1B—C2B—C3B—C4B2.4 (7)C1H—C2H—C3H—C4H1.7 (6)
N2B—C2B—C3B—C4B179.6 (4)N2H—C2H—C3H—C4H179.0 (4)
C2B—C3B—C4B—C5B−0.8 (6)C2H—C3H—C4H—C5H−0.1 (7)
C2B—C3B—C4B—C7B−177.6 (4)C2H—C3H—C4H—C7H−177.2 (4)
C3B—C4B—C5B—C6B0.2 (7)C3H—C4H—C5H—C6H−0.2 (7)
C7B—C4B—C5B—C6B177.0 (4)C7H—C4H—C5H—C6H176.9 (4)
C4B—C5B—C6B—C1B−1.0 (7)C4H—C5H—C6H—C1H−1.0 (7)
N1B—C1B—C6B—C5B−176.8 (4)N1H—C1H—C6H—C5H−177.5 (4)
C2B—C1B—C6B—C5B2.5 (6)C2H—C1H—C6H—C5H2.4 (6)
C3B—C4B—C7B—O4B−178.1 (4)C3H—C4H—C7H—O4H179.6 (4)
C5B—C4B—C7B—O4B5.1 (7)C5H—C4H—C7H—O4H2.5 (7)
C3B—C4B—C7B—O3B1.6 (6)C3H—C4H—C7H—O3H0.3 (7)
C5B—C4B—C7B—O3B−175.2 (4)C5H—C4H—C7H—O3H−176.8 (4)
C1B—N1B—C8B—C9B160.1 (4)C1H—N1H—C8H—C9H161.8 (4)
N1B—C8B—C9B—C10B63.9 (5)N1H—C8H—C9H—C10H62.3 (5)
C8B—C9B—C10B—C11B−109.4 (6)C8H—C9H—C10H—C11H−104.2 (5)
C8C—N1C—C1C—C6C2.9 (7)C8I—N1I—C1I—C2I−169.0 (4)
C8C—N1C—C1C—C2C−175.9 (4)C8I—N1I—C1I—C6I9.8 (6)
N1C—C1C—C2C—C3C176.2 (4)N1I—C1I—C2I—C3I176.4 (4)
C6C—C1C—C2C—C3C−2.7 (6)C6I—C1I—C2I—C3I−2.5 (6)
N1C—C1C—C2C—N2C−2.3 (6)N1I—C1I—C2I—N2I−1.6 (6)
C6C—C1C—C2C—N2C178.8 (4)C6I—C1I—C2I—N2I179.5 (4)
O2C—N2C—C2C—C3C−4.3 (6)O1I—N2I—C2I—C3I172.6 (4)
O1C—N2C—C2C—C3C175.7 (4)O2I—N2I—C2I—C3I−8.5 (5)
O2C—N2C—C2C—C1C174.3 (4)O1I—N2I—C2I—C1I−9.3 (6)
O1C—N2C—C2C—C1C−5.7 (6)O2I—N2I—C2I—C1I169.6 (4)
C1C—C2C—C3C—C4C1.5 (6)C1I—C2I—C3I—C4I1.6 (6)
N2C—C2C—C3C—C4C−179.9 (4)N2I—C2I—C3I—C4I179.7 (4)
C2C—C3C—C4C—C5C0.5 (6)C2I—C3I—C4I—C5I0.1 (6)
C2C—C3C—C4C—C7C−179.5 (4)C2I—C3I—C4I—C7I179.6 (4)
C3C—C4C—C5C—C6C−1.2 (6)C3I—C4I—C5I—C6I−0.7 (7)
C7C—C4C—C5C—C6C178.8 (4)C7I—C4I—C5I—C6I179.7 (4)
C4C—C5C—C6C—C1C−0.1 (7)C4I—C5I—C6I—C1I−0.3 (7)
N1C—C1C—C6C—C5C−177.0 (4)N1I—C1I—C6I—C5I−177.1 (4)
C2C—C1C—C6C—C5C2.0 (6)C2I—C1I—C6I—C5I1.8 (6)
C3C—C4C—C7C—O4C179.6 (4)C3I—C4I—C7I—O4I−179.1 (4)
C5C—C4C—C7C—O4C−0.3 (6)C5I—C4I—C7I—O4I0.5 (7)
C3C—C4C—C7C—O3C1.4 (6)C3I—C4I—C7I—O3I3.3 (6)
C5C—C4C—C7C—O3C−178.6 (4)C5I—C4I—C7I—O3I−177.1 (4)
C1C—N1C—C8C—C9C162.3 (4)C1I—N1I—C8I—C9I160.0 (4)
N1C—C8C—C9C—C10C64.6 (5)N1I—C8I—C9I—C10I64.0 (5)
C8C—C9C—C10C—C11C−107.0 (6)C8I—C9I—C10I—C11I−112.9 (5)
C8D—N1D—C1D—C2D178.9 (4)C8J—N1J—C1J—C6J−7.4 (6)
C8D—N1D—C1D—C6D0.0 (7)C8J—N1J—C1J—C2J170.8 (4)
N1D—C1D—C2D—C3D−179.3 (4)O2J—N2J—C2J—C3J8.6 (5)
C6D—C1D—C2D—C3D−0.4 (6)O1J—N2J—C2J—C3J−172.2 (3)
N1D—C1D—C2D—N2D2.0 (7)O2J—N2J—C2J—C1J−169.0 (3)
C6D—C1D—C2D—N2D−179.0 (4)O1J—N2J—C2J—C1J10.2 (5)
O2D—N2D—C2D—C3D3.1 (5)N1J—C1J—C2J—C3J−176.2 (4)
O1D—N2D—C2D—C3D−177.9 (4)C6J—C1J—C2J—C3J2.2 (5)
O2D—N2D—C2D—C1D−178.2 (4)N1J—C1J—C2J—N2J1.3 (6)
O1D—N2D—C2D—C1D0.9 (6)C6J—C1J—C2J—N2J179.6 (3)
C1D—C2D—C3D—C4D−0.4 (6)N2J—C2J—C3J—C4J−178.9 (3)
N2D—C2D—C3D—C4D178.3 (3)C1J—C2J—C3J—C4J−1.3 (6)
C2D—C3D—C4D—C5D0.6 (6)C2J—C3J—C4J—C5J−0.4 (6)
C2D—C3D—C4D—C7D−179.4 (4)C2J—C3J—C4J—C7J179.8 (4)
C3D—C4D—C5D—C6D0.0 (6)C3J—C4J—C5J—C6J1.2 (6)
C7D—C4D—C5D—C6D−180.0 (4)C7J—C4J—C5J—C6J−179.0 (4)
C4D—C5D—C6D—C1D−0.9 (6)C4J—C5J—C6J—C1J−0.3 (6)
N1D—C1D—C6D—C5D−180.0 (4)N1J—C1J—C6J—C5J177.0 (4)
C2D—C1D—C6D—C5D1.0 (6)C2J—C1J—C6J—C5J−1.4 (5)
C3D—C4D—C7D—O4D−0.5 (6)C3J—C4J—C7J—O4J176.9 (4)
C5D—C4D—C7D—O4D179.6 (4)C5J—C4J—C7J—O4J−2.9 (6)
C3D—C4D—C7D—O3D−178.9 (4)C3J—C4J—C7J—O3J−2.5 (6)
C5D—C4D—C7D—O3D1.1 (6)C5J—C4J—C7J—O3J177.7 (4)
C1D—N1D—C8D—C9D−163.1 (5)C1J—N1J—C8J—C9J−161.9 (3)
N1D—C8D—C9D—C10D−66.4 (6)N1J—C8J—C9J—C10J−64.6 (5)
C8D—C9D—C10D—C11D126.3 (7)C8J—C9J—C10J—C11J111.6 (5)
C8E—N1E—C1E—C6E−1.7 (6)C8K—N1K—C1K—C6K2.3 (6)
C8E—N1E—C1E—C2E177.2 (4)C8K—N1K—C1K—C2K−177.6 (4)
N1E—C1E—C2E—C3E−178.0 (4)N1K—C1K—C2K—C3K176.9 (4)
C6E—C1E—C2E—C3E1.0 (6)C6K—C1K—C2K—C3K−3.0 (5)
N1E—C1E—C2E—N2E0.5 (7)N1K—C1K—C2K—N2K−0.8 (6)
C6E—C1E—C2E—N2E179.5 (4)C6K—C1K—C2K—N2K179.3 (3)
O2E—N2E—C2E—C3E1.5 (6)O2K—N2K—C2K—C3K−1.8 (5)
O1E—N2E—C2E—C3E−178.5 (4)O1K—N2K—C2K—C3K178.8 (3)
O2E—N2E—C2E—C1E−177.0 (4)O2K—N2K—C2K—C1K176.1 (3)
O1E—N2E—C2E—C1E3.0 (6)O1K—N2K—C2K—C1K−3.3 (6)
C1E—C2E—C3E—C4E−0.4 (7)C1K—C2K—C3K—C4K0.3 (6)
N2E—C2E—C3E—C4E−179.0 (4)N2K—C2K—C3K—C4K178.1 (3)
C2E—C3E—C4E—C5E−0.1 (7)C2K—C3K—C4K—C5K2.2 (6)
C2E—C3E—C4E—C7E179.4 (4)C2K—C3K—C4K—C7K−176.4 (4)
C3E—C4E—C5E—C6E0.1 (7)C3K—C4K—C5K—C6K−1.9 (6)
C7E—C4E—C5E—C6E−179.4 (4)C7K—C4K—C5K—C6K176.7 (4)
C4E—C5E—C6E—C1E0.5 (7)C4K—C5K—C6K—C1K−0.9 (6)
N1E—C1E—C6E—C5E178.0 (4)N1K—C1K—C6K—C5K−176.6 (4)
C2E—C1E—C6E—C5E−1.0 (6)C2K—C1K—C6K—C5K3.3 (6)
C3E—C4E—C7E—O4E3.9 (7)C3K—C4K—C7K—O4K−179.4 (4)
C5E—C4E—C7E—O4E−176.6 (4)C5K—C4K—C7K—O4K2.0 (6)
C3E—C4E—C7E—O3E−176.6 (4)C3K—C4K—C7K—O3K2.3 (6)
C5E—C4E—C7E—O3E2.9 (6)C5K—C4K—C7K—O3K−176.2 (4)
C1E—N1E—C8E—C9E−173.1 (4)C1K—N1K—C8K—C9K161.5 (4)
N1E—C8E—C9E—C10E−58.3 (5)N1K—C8K—C9K—C10K62.6 (4)
C8E—C9E—C10E—C11E123.7 (5)C8K—C9K—C10K—C11K−104.8 (5)
C8F—N1F—C1F—C2F175.4 (4)C8L—N1L—C1L—C6L−1.0 (6)
C8F—N1F—C1F—C6F−4.5 (6)C8L—N1L—C1L—C2L177.6 (4)
N1F—C1F—C2F—C3F−179.0 (4)N1L—C1L—C2L—C3L−178.2 (4)
C6F—C1F—C2F—C3F0.9 (6)C6L—C1L—C2L—C3L0.5 (5)
N1F—C1F—C2F—N2F1.6 (7)N1L—C1L—C2L—N2L0.9 (6)
C6F—C1F—C2F—N2F−178.5 (4)C6L—C1L—C2L—N2L179.6 (3)
O2F—N2F—C2F—C3F4.1 (6)O1L—N2L—C2L—C3L−177.4 (4)
O1F—N2F—C2F—C3F−175.4 (4)O2L—N2L—C2L—C3L2.6 (5)
O2F—N2F—C2F—C1F−176.5 (4)O1L—N2L—C2L—C1L3.5 (6)
O1F—N2F—C2F—C1F4.0 (6)O2L—N2L—C2L—C1L−176.5 (4)
C1F—C2F—C3F—C4F−0.4 (7)C1L—C2L—C3L—C4L0.3 (6)
N2F—C2F—C3F—C4F179.0 (4)N2L—C2L—C3L—C4L−178.8 (3)
C2F—C3F—C4F—C5F0.5 (7)C2L—C3L—C4L—C5L−1.2 (6)
C2F—C3F—C4F—C7F−179.3 (4)C2L—C3L—C4L—C7L179.2 (3)
C3F—C4F—C5F—C6F−1.1 (7)C3L—C4L—C5L—C6L1.2 (6)
C7F—C4F—C5F—C6F178.7 (4)C7L—C4L—C5L—C6L−179.2 (4)
C4F—C5F—C6F—C1F1.7 (7)C4L—C5L—C6L—C1L−0.4 (6)
N1F—C1F—C6F—C5F178.4 (4)N1L—C1L—C6L—C5L178.3 (4)
C2F—C1F—C6F—C5F−1.5 (6)C2L—C1L—C6L—C5L−0.5 (6)
C3F—C4F—C7F—O4F2.3 (7)C3L—C4L—C7L—O4L2.6 (6)
C5F—C4F—C7F—O4F−177.5 (4)C5L—C4L—C7L—O4L−177.0 (4)
C3F—C4F—C7F—O3F−176.8 (4)C3L—C4L—C7L—O3L−178.0 (4)
C5F—C4F—C7F—O3F3.4 (6)C5L—C4L—C7L—O3L2.4 (5)
C1F—N1F—C8F—C9F−161.5 (4)C1L—N1L—C8L—C9L−175.9 (4)
N1F—C8F—C9F—C10F−65.7 (5)N1L—C8L—C9L—C10L−58.6 (5)
C8F—C9F—C10F—C11F123.0 (5)C8L—C9L—C10L—C11L121.8 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.862.002.643 (4)130
N1B—H1BA···O1B0.861.992.628 (5)130
N1C—H1CA···O1C0.861.982.631 (4)132
N1D—H1DA···O1D0.861.992.634 (5)130
N1E—H1EA···O1E0.862.012.637 (5)129
N1F—H1FA···O1F0.862.002.641 (4)130
N1G—H1GA···O1G0.861.982.624 (5)130
N1H—H1HA···O1H0.861.972.621 (5)131
N1I—H1IA···O1I0.861.992.632 (4)130
N1J—H1JA···O1J0.861.992.627 (4)131
N1K—H1KA···O1K0.861.962.615 (4)132
N1L—H1LA···O1L0.862.012.645 (4)130
O3A—H3AB···O4C0.821.802.612 (5)176
O3C—H3CB···O4A0.821.822.630 (4)172
O3B—H3BB···O4L0.821.812.626 (5)173
O3L—H3LB···O4B0.821.802.613 (5)169
O3D—H3DB···O4J0.821.802.618 (5)173
O3J—H3JB···O4D0.821.812.626 (5)175
O3E—H3EB···O4I0.821.812.624 (5)170
O3I—H3IB···O4E0.821.822.635 (5)174
O3G—H3GB···O4K0.821.802.616 (5)172
O3K—H3KB···O4G0.821.832.633 (5)163
O3F—H3FB···O4Hi0.821.792.605 (5)172
O3H—H3HB···O4Fii0.821.822.611 (5)164
C6B—H6BA···O2Hi0.932.453.169 (5)134
C6H—H6HA···O2Biii0.932.553.243 (5)131
C6I—H6IA···O2Cii0.932.533.218 (5)131
C6K—H6KA···O2Kiv0.932.403.149 (4)138
C9C—H9CB···O1B0.972.593.477 (6)152
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x, −y+1, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.862.002.643 (4)130
N1B—H1BA···O1B0.861.992.628 (5)130
N1C—H1CA···O1C0.861.982.631 (4)132
N1D—H1DA···O1D0.861.992.634 (5)130
N1E—H1EA···O1E0.862.012.637 (5)129
N1F—H1FA···O1F0.862.002.641 (4)130
N1G—H1GA···O1G0.861.982.624 (5)130
N1H—H1HA···O1H0.861.972.621 (5)131
N1I—H1IA···O1I0.861.992.632 (4)130
N1J—H1JA···O1J0.861.992.627 (4)131
N1K—H1KA···O1K0.861.962.615 (4)132
N1L—H1LA···O1L0.862.012.645 (4)130
O3A—H3AB···O4C0.821.802.612 (5)176
O3C—H3CB···O4A0.821.822.630 (4)172
O3B—H3BB···O4L0.821.812.626 (5)173
O3L—H3LB···O4B0.821.802.613 (5)169
O3D—H3DB···O4J0.821.802.618 (5)173
O3J—H3JB···O4D0.821.812.626 (5)175
O3E—H3EB···O4I0.821.812.624 (5)170
O3I—H3IB···O4E0.821.822.635 (5)174
O3G—H3GB···O4K0.821.802.616 (5)172
O3K—H3KB···O4G0.821.832.633 (5)163
O3F—H3FB···O4Hi0.821.792.605 (5)172
O3H—H3HB···O4Fii0.821.822.611 (5)164
C6B—H6BA···O2Hi0.932.453.169 (5)134
C6H—H6HA···O2Biii0.932.553.243 (5)131
C6I—H6IA···O2Cii0.932.533.218 (5)131
C6K—H6KA···O2Kiv0.932.403.149 (4)138
C9C—H9CB···O1B0.972.593.477 (6)152
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x, −y+1, z−1/2.
Acknowledgements top

SNNB, ASAR and HO are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the University Research grant No. 1001/PFARMASI/815026. HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SNNB and SRJ thank Universiti Sains Malaysia for post-doctoral research fellowships. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No.1001/PFIZIK/811012.

references
References top

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.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.

Ishida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett. 16, 1859–1863.

Kuzniewski, C. N., Gertsch, J., Wartmann, M. & Altmann, K.-H. (2008). Org. Lett. 10, 1183–1186.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Wu, Z., Rea, P. & Wickham, G. (2000). Tetrahedron Lett. 41, 9871–9874.