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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3329–o3330.
Published online 2010 November 27. doi:  10.1107/S1600536810048798
PMCID: PMC3011777

(5S)-4-(2,2-Dimethyl­prop­yl)-5-isopropyl-1,3,4-oxadiazinan-2-one

Abstract

The title compound, C11H22N2O2, has one chiral center and packs in the monoclinic space group P21. The asymmetric unit has five crystallographically independent mol­ecules, four of which engage in inter­molecular N—H(...)O hydrogen bonding.

Related literature

For related structures and background, see: Addison et al. (2008 [triangle]); Anderson et al. (2006 [triangle]); Burgeson et al. (2004 [triangle]); Casper et al. (2002 [triangle]); Rodrigues et al. (2006 [triangle]); Szczepura et al. (2004 [triangle]); Trepanier et al. (1968 [triangle]). The synthesis of the title compound is described by Casper et al. (2004 [triangle]). For literature related to crystallographic analysis, see: Allen (2002 [triangle]); Bernstein et al. (1995 [triangle]); Boeyens (1978 [triangle]); Bruno et al. (2004 [triangle]); Cremer & Pople (1975 [triangle]); Etter et al. (1990 [triangle]); Macrae et al. (2008 [triangle]); Spek (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3329-scheme1.jpg

Experimental

Crystal data

  • C11H22N2O2
  • M r = 214.3
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3329-efi1.jpg
  • a = 17.0330 (18) Å
  • b = 11.2270 (12) Å
  • c = 17.404 (2) Å
  • β = 100.073 (2)°
  • V = 3276.9 (6) Å3
  • Z = 10
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 193 K
  • 0.6 × 0.32 × 0.27 mm

Data collection

  • Bruker P4/R4/SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999 [triangle]) T min = 0.812, T max = 0.943
  • 16431 measured reflections
  • 7042 independent reflections
  • 4526 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.144
  • S = 1.03
  • 7042 reflections
  • 723 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]), publCIF (Westrip, 2010) [triangle] and Mercury (Macrae et al., 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048798/zl2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048798/zl2318Isup2.hkl

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

Acknowledgments

This material is based upon work supported by the US National Science Foundation (CHE-0348158) (to GMF) and the American Chemical Society Petroleum Research Fund (#407771B) (to SRH). GMF thanks Dr Robert McDonald, Dr Michael Ferguson, and the University of Alberta X-ray Crystallography Laboratory for the data collection.

supplementary crystallographic information

Comment

The fundamental structure of 1,3,4-oxadiazinan-2-one compounds has been known for nearly forty years (Trepanier et al., 1968). We are interested in studying the underlying factors for differing conformations of this heterocycle and for its use as a chiral auxiliary in aldol addition reactions (Casper et al., 2002; Burgeson et al., 2004).

The oxadiazinanone ring is well suited to accommodate H-bonded dimers of the R22(8) type (Bernstein et al., 1995; Etter et al., 1990). The H-bond occurs most naturally between the carbonyl oxygen on the first molecule and the nitrogen containing the hydrogen atom on the second molecule, and vice versa. The result is an eight-membered ring in which two of the connections are H-bonds. These H-bonded dimers have a strong propensity to form in the oxadiazinanone system (Anderson et al., 2006). A few examples of this type of H-bonding are seen in structures by Addison et al. (2008), Rodrigues et al. (2006), and Szczepura et al. (2004) (with REFCODES LOBVII, GEGZUO, and YAGJEW, respectively).

The title compound packs into a monoclinic, P21, space group. This compound is unusual in that there are five molecules in the asymmetric unit (see Figure 1). The best of these is illustrated in Figure 2. Of these five molecules, two pairs are engaged in R22(8) type H-bonding. The fifth molecule does not engage in H-bonding because the donor atom is surrounded by neopentyl substituents, effectively blocking any H-bonds to an acceptor atom. Figure 3 shows all five molecules in a wireframe style, with key atoms shown in a space-fill style, to highlight how the N—H is hemmed in by neopentyl substituents. Another, interactive, view in Figure 4 shows how inaccessible the donor N really is.

The number of crystallographically independent molecules in the asymmetric unit also warrants notice. Most of the structures in the Cambridge Structural Database have a Z' less than or equal to 1. According to the August 2010 edition of the CSD (Allen, 2002), 91.1% of the structures have a Z' less than or equal to 1. As Z' increases, the percentage of structures decreases (Z'=2, 7.7%; Z'=3, 0.42%; Z'=4, 0.40%). Only 0.014% (N=73) of structures in the CSD have a Z'=5, which is a property of this structure.

Since the conformation of the heterocycle is of some interest, structure overlays were conducted in Mercury (Macrae et al., 2008). Surprisingly, all five heterocycles exhibit the same conformation (seen in Figure 5); there is some swing observed in the isopropyl and neopentyl groups, but that deviation does not require the heterocycle to assume a different position in the crystal array. A Cremer-Pople ring analysis (Cremer & Pople, 1975; Boeyens, 1978), performed in PLATON (Spek, 2009), shows that all five molecules exhibit the 5E ring conformation, which is an envelope conformation with C5 as the flap apex. The data for the five oxadiazinanone rings are as follows: Ring 1 (O1—C6) - Q=0.511 (4); θ=56.7 (5)°; Φ=251.2 (5)°, Ring 2 (O21—C26) - Q=0.499 (4); θ=53.7 (5)°; Φ=253.9 (5)°, Ring 3 (O41—C46) - Q=0.510 (4); θ=56.7 (4)°; Φ=246.5 (5)°, Ring 4 (O61—C66) - Q=0.492 (5); θ=55.6 (5)°; Φ=239.9 (6)°, Ring 5 (O81—C86) - Q=0.500 (4); θ=55.9 (5)°; Φ=236.4 (5)°.

Upon conducting a Mogul geometry check (Bruno et al., 2004), the N4—C10 (1.490 (5) Å) and N24—C30 bonds (1.488 (5) Å) were flagged as being outside the typical range for a C—N bond (mean 1.46 ±0.01 Å). This bond is the one between the N atom of the heterocycle and the neopentyl substituent. This bond in the other three crystallographically independent molecules is not flagged. The bonds C50—C51 (1.508 (7) Å) and C90—C91 (1.507 (6) Å) were also flagged as unusual compared to the mean of 1.54 ±0.01 Å. One last bond, N84—C85, was considered unusual with a value of 1.463 (5) Å versus a mean of 1.49 ±0.01 Å. There is no obvious particular chemical or crystallographic explanation for these deviations. However, they still appear to be within an acceptable range. All angles were reported to be within normal limits.

Experimental

The title compound was prepared as previously reported (Casper et al. 2004). Single crystals were grown by vapor diffusion of hexane into an ethyl acetate solution of the title compound.

Refinement

All non-H atoms were refined anisotropically. All H atoms were initially identified through difference Fourier syntheses then removed and included in the refinement in the riding-model approximation (C–H = 0.98, 0.99 and 1.00 Å for CH3, CH2, and CH; Uiso(H) = 1.2Ueq(C) except for methyl groups, where Uiso(H) = 1.5Ueq(C)).

Figures

Fig. 1.
ORTEP view of the title compound showing the atomic numbering scheme of all five independent molecules in the asymmetric unit. Ellipsoids are shown at 50% probability displacement and hydrogen atoms are omitted for clarity.
Fig. 2.
ORTEP view of the title compound showing the atomic numbering scheme for the best of the five independent molecules. Ellipsoids are shown at 50% probability displacement and hydrogen atoms are omitted for clarity.
Fig. 3.
A view of the asymmetric unit in Mercury. The molecule that is not engaged in H-bonding has the N and H atoms shown in spacefill mode. Aliphatic substituents (C atoms shown in spacefill) surround this N–H and prohibit it from H-bonding with a ...
Fig. 4.
The Jmol enhanced figure of the title compound. The H-bonding situation can clearly be seen by manipulating the various radiobuttons.
Fig. 5.
An overlay of the five molecules in the asymmetric unit shown in Mercury. There is no significant variation of the oxadiazinanone ring.

Crystal data

C11H22N2O2F(000) = 1180
Mr = 214.3Dx = 1.086 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6729 reflections
a = 17.0330 (18) Åθ = 2.4–22.8°
b = 11.2270 (12) ŵ = 0.08 mm1
c = 17.404 (2) ÅT = 193 K
β = 100.073 (2)°Prism, colourless
V = 3276.9 (6) Å30.6 × 0.32 × 0.27 mm
Z = 10

Data collection

Bruker P4/R4/SMART 1000 CCD diffractometer4526 reflections with I > 2σ(I)
ω scansRint = 0.044
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1999)θmax = 26.4°, θmin = 1.2°
Tmin = 0.812, Tmax = 0.943h = −21→21
16431 measured reflectionsk = −11→14
7042 independent reflectionsl = −19→21

Refinement

Refinement on F21 restraint
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.052w = 1/[σ2(Fo2) + (0.0763P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.144(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.27 e Å3
7042 reflectionsΔρmin = −0.17 e Å3
723 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.4885 (2)0.4683 (3)−0.06758 (17)0.0693 (9)
C20.4247 (3)0.4157 (5)−0.0465 (3)0.0679 (13)
N30.4016 (2)0.4554 (4)0.0188 (3)0.0625 (10)
N40.44061 (17)0.5387 (3)0.07359 (18)0.0427 (7)
C50.5244 (2)0.5438 (3)0.0642 (2)0.0418 (9)
H50.54890.61460.09410.05*
C60.5273 (3)0.5655 (4)−0.0204 (2)0.0585 (11)
H6A0.50.6414−0.03730.07*
H6B0.58340.572−0.02780.07*
C70.5696 (2)0.4339 (4)0.0995 (2)0.0472 (9)
H70.54190.36220.07370.057*
C80.6560 (2)0.4309 (5)0.0861 (3)0.0677 (13)
H8A0.68210.35860.10960.102*
H8B0.68450.50110.11020.102*
H8C0.65680.43110.02990.102*
C90.5678 (3)0.4252 (5)0.1864 (3)0.0690 (13)
H9A0.5970.35390.20780.103*
H9B0.51240.41990.19450.103*
H9C0.59290.49610.2130.103*
C100.3986 (2)0.6556 (3)0.0666 (2)0.0505 (10)
H10A0.35270.65170.0230.061*
H10B0.43540.71790.05390.061*
C110.3688 (2)0.6901 (3)0.1414 (2)0.0443 (9)
C120.3260 (3)0.8094 (4)0.1264 (3)0.0634 (12)
H12A0.28070.80090.08340.095*
H12B0.36310.86910.11240.095*
H12C0.30670.8350.17360.095*
C130.3113 (3)0.5967 (4)0.1610 (3)0.0792 (15)
H13A0.26680.58850.11740.119*
H13B0.2910.62090.2080.119*
H13C0.33910.52020.17050.119*
C140.4384 (3)0.7049 (5)0.2076 (3)0.0706 (13)
H14A0.47510.76510.19340.106*
H14B0.46650.62880.21750.106*
H14C0.41890.73040.25470.106*
O150.3927 (2)0.3348 (4)−0.0854 (3)0.1060 (15)
H30.365 (3)0.416 (5)0.035 (3)0.073 (16)*
O210.60240 (16)0.0228 (3)0.35395 (17)0.0629 (8)
C220.6241 (2)0.0932 (4)0.4166 (2)0.0528 (11)
N230.56820 (19)0.1295 (3)0.4561 (2)0.0483 (9)
N240.48479 (16)0.1070 (3)0.43763 (17)0.0439 (7)
C250.4650 (2)0.0769 (4)0.3543 (2)0.0477 (10)
H250.40990.04290.34460.057*
C260.5212 (2)−0.0197 (4)0.3368 (3)0.0602 (11)
H26A0.5153−0.0910.36880.072*
H26B0.5077−0.04250.28110.072*
C270.4643 (2)0.1884 (4)0.3030 (2)0.0557 (10)
H270.5190.22410.31280.067*
C280.4435 (3)0.1552 (6)0.2171 (3)0.0893 (17)
H28A0.48160.09580.20470.134*
H28B0.44610.22640.1850.134*
H28C0.38950.1220.20610.134*
C290.4062 (3)0.2798 (5)0.3235 (3)0.0782 (14)
H29A0.40670.35010.29020.117*
H29B0.42170.30290.37830.117*
H29C0.35240.24560.31520.117*
C300.4607 (3)0.0152 (4)0.4906 (3)0.0594 (11)
H30A0.5086−0.01210.5270.071*
H30B0.4383−0.05430.45920.071*
C310.3996 (2)0.0603 (4)0.5375 (2)0.0539 (11)
C320.3795 (3)−0.0402 (6)0.5887 (3)0.0896 (17)
H32A0.4276−0.06410.6250.134*
H32B0.359−0.10830.5560.134*
H32C0.3388−0.01330.61830.134*
C330.4337 (4)0.1663 (6)0.5866 (3)0.115 (3)
H33A0.48220.1420.62210.172*
H33B0.39430.19520.61710.172*
H33C0.44650.23010.55240.172*
C340.3249 (3)0.0960 (5)0.4830 (3)0.0831 (16)
H34A0.33680.16180.44990.125*
H34B0.28460.12150.51340.125*
H34C0.30460.02790.45020.125*
O350.69335 (16)0.1255 (4)0.43234 (17)0.0761 (10)
H230.584 (2)0.169 (4)0.492 (3)0.051 (13)*
O410.26808 (14)0.8230 (3)0.31233 (16)0.0557 (7)
C420.2958 (2)0.7617 (4)0.3774 (2)0.0442 (9)
N430.24610 (18)0.6941 (3)0.4097 (2)0.0474 (8)
N440.16241 (17)0.6874 (3)0.38521 (18)0.0481 (8)
C450.1355 (2)0.7981 (4)0.3434 (2)0.0526 (11)
H450.07870.78610.31810.063*
C460.1835 (2)0.8159 (5)0.2790 (2)0.0596 (11)
H46A0.17410.74860.24180.071*
H46B0.16640.89020.25020.071*
C470.1371 (2)0.9001 (4)0.4006 (3)0.0637 (12)
H470.1930.90720.42970.076*
C480.1156 (5)1.0160 (7)0.3609 (5)0.134 (3)
H48A0.11721.0790.40010.201*
H48B0.06171.01090.33010.201*
H48C0.15361.03450.32640.201*
C490.0835 (4)0.8758 (7)0.4601 (4)0.117 (2)
H49A0.09820.79950.4860.176*
H49B0.02780.87260.43350.176*
H49C0.08980.93970.4990.176*
C500.1397 (3)0.5776 (5)0.3403 (3)0.0758 (14)
H50A0.17910.56320.30570.091*
H50B0.08730.59060.30660.091*
C510.1346 (3)0.4674 (5)0.3887 (3)0.0726 (14)
C52A0.2148 (10)0.4158 (14)0.4062 (10)0.099 (5)0.5
H52A0.21360.34370.43760.148*0.5
H52B0.25150.47380.43520.148*0.5
H52C0.23280.39560.35730.148*0.5
C53A0.0741 (8)0.3832 (14)0.3425 (10)0.099 (5)0.5
H53A0.07010.31090.37310.149*0.5
H53B0.09140.3620.29340.149*0.5
H53C0.0220.42240.33120.149*0.5
C54A0.1074 (11)0.5004 (16)0.4667 (10)0.116 (6)0.5
H54A0.10440.42810.49750.175*0.5
H54B0.05470.53820.45560.175*0.5
H54C0.14580.55580.49610.175*0.5
C52B0.2081 (13)0.4386 (14)0.4517 (9)0.110 (6)0.5
H52D0.25490.4270.42680.164*0.5
H52E0.1980.36570.47940.164*0.5
H52F0.2180.50480.48890.164*0.5
C53B0.1269 (12)0.3535 (13)0.3335 (9)0.110 (5)0.5
H53D0.17540.3450.3110.164*0.5
H53E0.08080.36310.29140.164*0.5
H53F0.11950.28230.3640.164*0.5
C54B0.0622 (11)0.4802 (16)0.4233 (13)0.130 (7)0.5
H54D0.05630.41030.45560.196*0.5
H54E0.01550.48680.38170.196*0.5
H54F0.06650.5520.45580.196*0.5
O550.36702 (14)0.7706 (3)0.40520 (15)0.0533 (7)
H430.262 (2)0.673 (3)0.459 (2)0.041 (10)*
O61−0.06692 (15)0.3012 (3)−0.09221 (17)0.0681 (9)
C62−0.0031 (2)0.3696 (4)−0.0965 (3)0.0547 (11)
N630.0563 (2)0.3695 (3)−0.03533 (19)0.0466 (8)
N640.05885 (16)0.3060 (3)0.03561 (18)0.0431 (7)
C65−0.0238 (2)0.2907 (4)0.0483 (3)0.0546 (11)
H65−0.02280.2340.09280.066*
C66−0.0709 (2)0.2334 (5)−0.0230 (3)0.0670 (14)
H66A−0.050.1522−0.02890.08*
H66B−0.12730.2259−0.01650.08*
C67−0.0578 (2)0.4086 (4)0.0716 (3)0.0648 (13)
H67−0.06590.46190.02480.078*
C68−0.1395 (3)0.3876 (6)0.0954 (4)0.118 (3)
H68A−0.17470.34670.0530.177*
H68B−0.1630.46430.10570.177*
H68C−0.13270.33830.14260.177*
C69−0.0022 (4)0.4701 (7)0.1355 (4)0.112 (2)
H69A−0.02630.5450.14870.168*
H69B0.04830.48690.1180.168*
H69C0.00770.41870.18170.168*
C700.1029 (2)0.1934 (4)0.0357 (2)0.0482 (9)
H70A0.10850.1742−0.01860.058*
H70B0.07130.1290.05430.058*
C710.1850 (2)0.1955 (4)0.0860 (3)0.0574 (11)
C720.2217 (3)0.0725 (4)0.0846 (4)0.0850 (17)
H72A0.18690.01360.10310.128*
H72B0.2740.07170.11860.128*
H72C0.2280.05290.03110.128*
C730.2369 (3)0.2847 (6)0.0590 (6)0.135 (3)
H73A0.24330.26620.00540.203*
H73B0.28910.28380.09310.203*
H73C0.21290.36390.06040.203*
C740.1731 (5)0.2199 (8)0.1695 (4)0.151 (4)
H74A0.13810.15890.18550.227*
H74B0.14880.29850.17220.227*
H74C0.22480.21790.20450.227*
O75−0.00226 (17)0.4282 (4)−0.15440 (18)0.0753 (10)
H630.092 (2)0.422 (4)−0.030 (2)0.039 (11)*
O810.26791 (18)0.5980 (3)0.87572 (16)0.0671 (8)
C820.2004 (3)0.5404 (4)0.8848 (2)0.0540 (10)
N830.1615 (2)0.4771 (3)0.82481 (18)0.0471 (8)
N840.18487 (17)0.4653 (3)0.75098 (17)0.0410 (7)
C850.2253 (2)0.5750 (3)0.7346 (2)0.0445 (9)
H850.2480.56150.68620.053*
C860.2943 (3)0.5952 (4)0.8008 (3)0.0614 (12)
H86A0.33390.53050.8010.074*
H86B0.32070.67150.79260.074*
C870.1666 (3)0.6781 (4)0.7187 (3)0.0571 (11)
H870.1440.69270.76710.068*
C880.2050 (4)0.7922 (5)0.6981 (3)0.0865 (16)
H88A0.16460.85510.68820.13*
H88B0.22850.77980.65120.13*
H88C0.24680.81590.74150.13*
C890.0988 (3)0.6471 (5)0.6541 (4)0.111 (2)
H89A0.07410.57240.66680.167*
H89B0.11910.63760.60510.167*
H89C0.0590.7110.64840.167*
C900.2337 (2)0.3574 (4)0.7488 (3)0.0539 (10)
H90A0.26310.34150.80210.065*
H90B0.27360.37290.71490.065*
C910.1870 (3)0.2476 (4)0.7195 (3)0.0619 (12)
C920.2443 (4)0.1445 (5)0.7213 (5)0.114 (2)
H92A0.26510.12290.77570.172*
H92B0.28860.16760.69530.172*
H92C0.21640.0760.69420.172*
C930.1213 (5)0.2203 (5)0.7643 (5)0.126 (3)
H93A0.14420.20630.81920.189*
H93B0.09250.14890.74250.189*
H93C0.08430.28780.76030.189*
C940.1492 (5)0.2668 (7)0.6349 (4)0.129 (3)
H94A0.11890.19560.6150.193*
H94B0.19090.28180.60380.193*
H94C0.11310.33550.6310.193*
O950.1774 (2)0.5505 (3)0.94701 (17)0.0708 (9)
H830.111 (3)0.459 (4)0.828 (2)0.057 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.094 (2)0.066 (2)0.0474 (19)0.018 (2)0.0094 (16)−0.0103 (16)
C20.062 (3)0.061 (3)0.071 (3)0.019 (3)−0.016 (3)−0.021 (3)
N30.0434 (19)0.051 (2)0.091 (3)0.0002 (18)0.008 (2)−0.019 (2)
N40.0435 (17)0.0341 (17)0.0500 (19)0.0035 (14)0.0072 (14)−0.0024 (14)
C50.046 (2)0.039 (2)0.042 (2)−0.0077 (17)0.0120 (16)−0.0003 (16)
C60.072 (3)0.057 (3)0.051 (3)0.009 (2)0.023 (2)0.007 (2)
C70.041 (2)0.052 (3)0.048 (2)0.0035 (18)0.0075 (17)0.0005 (18)
C80.044 (2)0.096 (4)0.065 (3)0.011 (2)0.016 (2)−0.002 (3)
C90.073 (3)0.083 (3)0.056 (3)0.028 (3)0.024 (2)0.024 (2)
C100.061 (2)0.043 (2)0.045 (2)0.0172 (19)0.0050 (19)0.0033 (17)
C110.055 (2)0.035 (2)0.045 (2)0.0106 (18)0.0135 (17)0.0044 (17)
C120.085 (3)0.047 (2)0.063 (3)0.024 (2)0.025 (2)0.005 (2)
C130.085 (3)0.051 (3)0.115 (4)0.007 (3)0.054 (3)0.008 (3)
C140.090 (3)0.073 (3)0.047 (3)0.021 (3)0.004 (2)−0.013 (2)
O150.095 (3)0.083 (3)0.121 (3)0.017 (2)−0.034 (2)−0.060 (2)
O210.0514 (16)0.087 (2)0.0508 (18)0.0006 (16)0.0119 (13)−0.0258 (16)
C220.045 (2)0.077 (3)0.037 (2)0.001 (2)0.0083 (17)−0.013 (2)
N230.0409 (18)0.066 (2)0.037 (2)−0.0028 (17)0.0055 (15)−0.0118 (17)
N240.0366 (16)0.054 (2)0.0412 (18)−0.0047 (14)0.0076 (13)−0.0021 (15)
C250.039 (2)0.056 (3)0.046 (2)−0.0114 (18)0.0031 (16)−0.0085 (18)
C260.057 (2)0.067 (3)0.057 (3)−0.011 (2)0.011 (2)−0.018 (2)
C270.050 (2)0.074 (3)0.040 (2)−0.004 (2)0.0008 (17)0.000 (2)
C280.094 (4)0.119 (5)0.048 (3)0.002 (4)−0.007 (3)−0.007 (3)
C290.081 (3)0.081 (4)0.072 (3)0.015 (3)0.012 (3)0.017 (3)
C300.060 (2)0.057 (3)0.065 (3)0.006 (2)0.020 (2)0.011 (2)
C310.060 (3)0.054 (3)0.052 (2)−0.013 (2)0.021 (2)−0.0082 (19)
C320.108 (4)0.097 (4)0.075 (4)−0.007 (4)0.049 (3)0.012 (3)
C330.141 (5)0.138 (6)0.080 (4)−0.077 (5)0.061 (4)−0.058 (4)
C340.056 (3)0.086 (4)0.115 (4)0.002 (3)0.036 (3)0.010 (3)
O350.0401 (16)0.135 (3)0.0543 (19)−0.0083 (18)0.0124 (13)−0.0325 (19)
O410.0426 (14)0.078 (2)0.0464 (16)0.0020 (14)0.0070 (12)0.0207 (14)
C420.038 (2)0.053 (2)0.042 (2)0.0055 (19)0.0077 (17)0.0018 (18)
N430.0388 (17)0.061 (2)0.041 (2)0.0029 (16)0.0049 (14)0.0135 (17)
N440.0369 (16)0.057 (2)0.047 (2)−0.0061 (16)−0.0007 (14)0.0031 (16)
C450.035 (2)0.064 (3)0.056 (3)0.0010 (19)0.0001 (17)0.008 (2)
C460.049 (2)0.075 (3)0.050 (3)0.004 (2)−0.0031 (19)0.018 (2)
C470.043 (2)0.062 (3)0.086 (4)0.009 (2)0.009 (2)0.009 (3)
C480.167 (7)0.094 (5)0.138 (7)0.065 (5)0.018 (5)0.020 (5)
C490.125 (5)0.121 (6)0.124 (6)0.006 (4)0.071 (5)−0.018 (4)
C500.088 (4)0.079 (4)0.055 (3)−0.029 (3)−0.003 (2)−0.001 (3)
C510.089 (4)0.065 (3)0.059 (3)−0.018 (3)0.003 (3)−0.002 (3)
C52A0.108 (10)0.055 (7)0.118 (14)0.012 (7)−0.021 (11)−0.014 (9)
C53A0.088 (9)0.077 (11)0.121 (12)−0.021 (8)−0.014 (9)0.000 (8)
C54A0.135 (15)0.111 (12)0.113 (13)−0.048 (11)0.048 (10)0.036 (10)
C52B0.179 (16)0.056 (9)0.082 (11)−0.013 (9)−0.010 (12)0.012 (7)
C53B0.176 (17)0.058 (8)0.084 (9)−0.016 (11)−0.005 (12)−0.015 (6)
C54B0.124 (14)0.102 (11)0.18 (2)−0.054 (11)0.081 (13)−0.015 (13)
O550.0359 (14)0.0705 (19)0.0539 (17)0.0041 (13)0.0090 (12)0.0103 (14)
O610.0407 (15)0.103 (3)0.0592 (19)−0.0076 (16)0.0054 (13)0.0175 (18)
C620.035 (2)0.079 (3)0.052 (3)0.012 (2)0.0137 (19)0.015 (2)
N630.0367 (17)0.058 (2)0.047 (2)0.0010 (18)0.0126 (15)0.0105 (16)
N640.0358 (16)0.0461 (19)0.0489 (19)0.0097 (14)0.0116 (13)0.0123 (14)
C650.040 (2)0.067 (3)0.060 (3)0.012 (2)0.0177 (19)0.029 (2)
C660.037 (2)0.083 (4)0.081 (3)−0.004 (2)0.012 (2)0.022 (3)
C670.056 (2)0.083 (3)0.063 (3)0.034 (2)0.031 (2)0.032 (3)
C680.088 (4)0.130 (6)0.159 (6)0.046 (4)0.083 (4)0.063 (5)
C690.128 (5)0.125 (5)0.082 (4)0.071 (5)0.016 (4)−0.016 (4)
C700.0370 (19)0.040 (2)0.067 (3)0.0046 (18)0.0091 (18)−0.0033 (19)
C710.043 (2)0.047 (2)0.076 (3)0.014 (2)−0.0071 (19)−0.004 (2)
C720.052 (3)0.056 (3)0.138 (5)0.021 (2)−0.011 (3)−0.008 (3)
C730.045 (3)0.078 (4)0.267 (10)−0.013 (3)−0.019 (4)0.047 (5)
C740.173 (7)0.174 (8)0.083 (5)0.106 (7)−0.041 (5)−0.021 (5)
O750.0564 (17)0.121 (3)0.0505 (19)0.0068 (18)0.0150 (14)0.0320 (19)
O810.081 (2)0.073 (2)0.0465 (17)−0.0336 (17)0.0100 (15)−0.0064 (15)
C820.075 (3)0.046 (2)0.041 (2)−0.014 (2)0.013 (2)0.0003 (19)
N830.053 (2)0.050 (2)0.0419 (19)−0.0141 (17)0.0191 (15)−0.0075 (15)
N840.0451 (16)0.0406 (17)0.0418 (18)−0.0061 (15)0.0201 (13)−0.0026 (14)
C850.050 (2)0.044 (2)0.044 (2)−0.0114 (18)0.0204 (18)−0.0033 (17)
C860.059 (3)0.067 (3)0.060 (3)−0.026 (2)0.015 (2)0.001 (2)
C870.081 (3)0.043 (2)0.054 (3)−0.001 (2)0.030 (2)0.0006 (19)
C880.118 (4)0.050 (3)0.086 (4)−0.022 (3)0.004 (3)0.008 (3)
C890.077 (4)0.062 (4)0.177 (7)0.008 (3)−0.027 (4)0.022 (4)
C900.050 (2)0.056 (3)0.058 (3)0.003 (2)0.0167 (19)0.004 (2)
C910.080 (3)0.048 (3)0.064 (3)0.001 (2)0.029 (2)0.001 (2)
C920.151 (6)0.057 (4)0.150 (6)0.030 (4)0.067 (5)0.006 (4)
C930.162 (6)0.064 (4)0.178 (7)−0.050 (4)0.102 (6)−0.033 (4)
C940.201 (8)0.088 (5)0.082 (5)−0.001 (5)−0.017 (5)−0.028 (4)
O950.107 (2)0.068 (2)0.0438 (18)−0.0209 (19)0.0316 (16)−0.0081 (15)

Geometric parameters (Å, °)

O1—C21.342 (6)C51—C52A1.465 (16)
O1—C61.453 (6)C51—C54B1.472 (17)
C2—O151.205 (5)C51—C53A1.521 (15)
C2—N31.342 (6)C51—C52B1.548 (18)
N3—N41.415 (5)C51—C54A1.554 (18)
N3—H30.85 (5)C51—C53B1.591 (15)
N4—C51.466 (4)C52A—H52A0.98
N4—C101.489 (5)C52A—H52B0.98
C5—C61.502 (5)C52A—H52C0.98
C5—C71.525 (5)C53A—H53A0.98
C5—H51C53A—H53B0.98
C6—H6A0.99C53A—H53C0.98
C6—H6B0.99C54A—H54A0.98
C7—C91.522 (6)C54A—H54B0.98
C7—C81.530 (5)C54A—H54C0.98
C7—H71C52B—H52D0.98
C8—H8A0.98C52B—H52E0.98
C8—H8B0.98C52B—H52F0.98
C8—H8C0.98C53B—H53D0.98
C9—H9A0.98C53B—H53E0.98
C9—H9B0.98C53B—H53F0.98
C9—H9C0.98C54B—H54D0.98
C10—C111.529 (5)C54B—H54E0.98
C10—H10A0.99C54B—H54F0.98
C10—H10B0.99O61—C621.343 (5)
C11—C141.511 (6)O61—C661.436 (5)
C11—C131.513 (6)C62—O751.206 (5)
C11—C121.526 (5)C62—N631.335 (5)
C12—H12A0.98N63—N641.420 (4)
C12—H12B0.98N63—H630.84 (4)
C12—H12C0.98N64—C701.470 (5)
C13—H13A0.98N64—C651.473 (4)
C13—H13B0.98C65—C661.501 (7)
C13—H13C0.98C65—C671.527 (6)
C14—H14A0.98C65—H651
C14—H14B0.98C66—H66A0.99
C14—H14C0.98C66—H66B0.99
O21—C221.345 (5)C67—C691.498 (8)
O21—C261.444 (5)C67—C681.538 (6)
C22—O351.219 (5)C67—H671
C22—N231.331 (5)C68—H68A0.98
N23—N241.423 (4)C68—H68B0.98
N23—H230.78 (4)C68—H68C0.98
N24—C251.469 (5)C69—H69A0.98
N24—C301.487 (5)C69—H69B0.98
C25—C261.511 (6)C69—H69C0.98
C25—C271.537 (6)C70—C711.514 (5)
C25—H251C70—H70A0.99
C26—H26A0.99C70—H70B0.99
C26—H26B0.99C71—C731.467 (8)
C27—C291.512 (7)C71—C721.518 (6)
C27—C281.521 (6)C71—C741.527 (8)
C27—H271C72—H72A0.98
C28—H28A0.98C72—H72B0.98
C28—H28B0.98C72—H72C0.98
C28—H28C0.98C73—H73A0.98
C29—H29A0.98C73—H73B0.98
C29—H29B0.98C73—H73C0.98
C29—H29C0.98C74—H74A0.98
C30—C311.517 (5)C74—H74B0.98
C30—H30A0.99C74—H74C0.98
C30—H30B0.99O81—C821.352 (5)
C31—C341.502 (7)O81—C861.452 (5)
C31—C321.513 (7)C82—O951.220 (5)
C31—C331.521 (7)C82—N831.339 (5)
C32—H32A0.98N83—N841.417 (4)
C32—H32B0.98N83—H830.89 (4)
C32—H32C0.98N84—C851.463 (5)
C33—H33A0.98N84—C901.473 (5)
C33—H33B0.98C85—C861.513 (6)
C33—H33C0.98C85—C871.522 (6)
C34—H34A0.98C85—H851
C34—H34B0.98C86—H86A0.99
C34—H34C0.98C86—H86B0.99
O41—C421.339 (4)C87—C891.504 (7)
O41—C461.459 (5)C87—C881.510 (7)
C42—O551.229 (4)C87—H871
C42—N431.332 (5)C88—H88A0.98
N43—N441.417 (4)C88—H88B0.98
N43—H430.88 (4)C88—H88C0.98
N44—C451.473 (5)C89—H89A0.98
N44—C501.473 (6)C89—H89B0.98
C45—C461.512 (6)C89—H89C0.98
C45—C471.513 (7)C90—C911.507 (6)
C45—H451C90—H90A0.99
C46—H46A0.99C90—H90B0.99
C46—H46B0.99C91—C931.503 (7)
C47—C481.489 (8)C91—C921.511 (7)
C47—C491.520 (8)C91—C941.516 (8)
C47—H471C92—H92A0.98
C48—H48A0.98C92—H92B0.98
C48—H48B0.98C92—H92C0.98
C48—H48C0.98C93—H93A0.98
C49—H49A0.98C93—H93B0.98
C49—H49B0.98C93—H93C0.98
C49—H49C0.98C94—H94A0.98
C50—C511.507 (7)C94—H94B0.98
C50—H50A0.99C94—H94C0.98
C50—H50B0.99
C2—O1—C6119.0 (3)C54B—C51—C53A74.9 (10)
O15—C2—N3123.8 (6)C50—C51—C53A108.4 (7)
O15—C2—O1119.1 (5)C54B—C51—C52B111.2 (12)
N3—C2—O1117.1 (4)C50—C51—C52B116.6 (7)
C2—N3—N4128.2 (4)C53A—C51—C52B129.3 (9)
C2—N3—H3117 (3)C52A—C51—C54A108.8 (10)
N4—N3—H3113 (4)C50—C51—C54A110.3 (7)
N3—N4—C5107.6 (3)C53A—C51—C54A109.4 (10)
N3—N4—C10111.4 (3)C52B—C51—C54A76.0 (10)
C5—N4—C10114.8 (3)C52A—C51—C53B77.5 (10)
N4—C5—C6108.3 (3)C54B—C51—C53B109.8 (11)
N4—C5—C7110.9 (3)C50—C51—C53B109.2 (7)
C6—C5—C7115.2 (3)C52B—C51—C53B103.4 (10)
N4—C5—H5107.4C54A—C51—C53B135.5 (9)
C6—C5—H5107.4C51—C52A—H52A109.5
C7—C5—H5107.4C51—C52A—H52B109.5
O1—C6—C5110.1 (3)H52A—C52A—H52B109.5
O1—C6—H6A109.6C51—C52A—H52C109.5
C5—C6—H6A109.6H52A—C52A—H52C109.5
O1—C6—H6B109.6H52B—C52A—H52C109.5
C5—C6—H6B109.6C51—C53A—H53A109.5
H6A—C6—H6B108.2C51—C53A—H53B109.5
C9—C7—C5110.8 (3)H53A—C53A—H53B109.5
C9—C7—C8109.7 (3)C51—C53A—H53C109.5
C5—C7—C8112.8 (3)H53A—C53A—H53C109.5
C9—C7—H7107.8H53B—C53A—H53C109.5
C5—C7—H7107.8C51—C54A—H54A109.5
C8—C7—H7107.8C51—C54A—H54B109.5
C7—C8—H8A109.5H54A—C54A—H54B109.5
C7—C8—H8B109.5C51—C54A—H54C109.5
H8A—C8—H8B109.5H54A—C54A—H54C109.5
C7—C8—H8C109.5H54B—C54A—H54C109.5
H8A—C8—H8C109.5C51—C52B—H52D109.5
H8B—C8—H8C109.5C51—C52B—H52E109.5
C7—C9—H9A109.5H52D—C52B—H52E109.5
C7—C9—H9B109.5C51—C52B—H52F109.5
H9A—C9—H9B109.5H52D—C52B—H52F109.5
C7—C9—H9C109.5H52E—C52B—H52F109.5
H9A—C9—H9C109.5C51—C53B—H53D109.5
H9B—C9—H9C109.5C51—C53B—H53E109.5
N4—C10—C11112.3 (3)H53D—C53B—H53E109.5
N4—C10—H10A109.1C51—C53B—H53F109.5
C11—C10—H10A109.1H53D—C53B—H53F109.5
N4—C10—H10B109.1H53E—C53B—H53F109.5
C11—C10—H10B109.1C51—C54B—H54D109.5
H10A—C10—H10B107.9C51—C54B—H54E109.5
C14—C11—C13110.9 (4)H54D—C54B—H54E109.5
C14—C11—C12108.8 (4)C51—C54B—H54F109.5
C13—C11—C12109.8 (3)H54D—C54B—H54F109.5
C14—C11—C10110.1 (3)H54E—C54B—H54F109.5
C13—C11—C10109.9 (4)C62—O61—C66120.5 (3)
C12—C11—C10107.2 (3)O75—C62—N63123.2 (4)
C11—C12—H12A109.5O75—C62—O61119.1 (4)
C11—C12—H12B109.5N63—C62—O61117.7 (4)
H12A—C12—H12B109.5C62—N63—N64126.6 (3)
C11—C12—H12C109.5C62—N63—H63122 (3)
H12A—C12—H12C109.5N64—N63—H63110 (3)
H12B—C12—H12C109.5N63—N64—C70111.7 (3)
C11—C13—H13A109.5N63—N64—C65107.8 (3)
C11—C13—H13B109.5C70—N64—C65113.6 (3)
H13A—C13—H13B109.5N64—C65—C66108.2 (3)
C11—C13—H13C109.5N64—C65—C67110.8 (4)
H13A—C13—H13C109.5C66—C65—C67114.8 (4)
H13B—C13—H13C109.5N64—C65—H65107.6
C11—C14—H14A109.5C66—C65—H65107.6
C11—C14—H14B109.5C67—C65—H65107.6
H14A—C14—H14B109.5O61—C66—C65111.7 (4)
C11—C14—H14C109.5O61—C66—H66A109.3
H14A—C14—H14C109.5C65—C66—H66A109.3
H14B—C14—H14C109.5O61—C66—H66B109.3
C22—O21—C26118.6 (3)C65—C66—H66B109.3
O35—C22—N23123.0 (4)H66A—C66—H66B107.9
O35—C22—O21118.3 (3)C69—C67—C65112.2 (4)
N23—C22—O21118.6 (4)C69—C67—C68110.8 (5)
C22—N23—N24127.2 (4)C65—C67—C68109.9 (5)
C22—N23—H23114 (3)C69—C67—H67107.9
N24—N23—H23118 (3)C65—C67—H67107.9
N23—N24—C25108.1 (3)C68—C67—H67107.9
N23—N24—C30110.9 (3)C67—C68—H68A109.5
C25—N24—C30114.3 (3)C67—C68—H68B109.5
N24—C25—C26108.7 (3)H68A—C68—H68B109.5
N24—C25—C27111.3 (3)C67—C68—H68C109.5
C26—C25—C27114.0 (3)H68A—C68—H68C109.5
N24—C25—H25107.5H68B—C68—H68C109.5
C26—C25—H25107.5C67—C69—H69A109.5
C27—C25—H25107.5C67—C69—H69B109.5
O21—C26—C25109.8 (3)H69A—C69—H69B109.5
O21—C26—H26A109.7C67—C69—H69C109.5
C25—C26—H26A109.7H69A—C69—H69C109.5
O21—C26—H26B109.7H69B—C69—H69C109.5
C25—C26—H26B109.7N64—C70—C71114.0 (3)
H26A—C26—H26B108.2N64—C70—H70A108.8
C29—C27—C28110.4 (4)C71—C70—H70A108.8
C29—C27—C25110.7 (3)N64—C70—H70B108.8
C28—C27—C25110.4 (4)C71—C70—H70B108.8
C29—C27—H27108.4H70A—C70—H70B107.7
C28—C27—H27108.4C73—C71—C70111.9 (4)
C25—C27—H27108.4C73—C71—C72110.0 (4)
C27—C28—H28A109.5C70—C71—C72108.5 (4)
C27—C28—H28B109.5C73—C71—C74111.7 (6)
H28A—C28—H28B109.5C70—C71—C74106.9 (4)
C27—C28—H28C109.5C72—C71—C74107.5 (5)
H28A—C28—H28C109.5C71—C72—H72A109.5
H28B—C28—H28C109.5C71—C72—H72B109.5
C27—C29—H29A109.5H72A—C72—H72B109.5
C27—C29—H29B109.5C71—C72—H72C109.5
H29A—C29—H29B109.5H72A—C72—H72C109.5
C27—C29—H29C109.5H72B—C72—H72C109.5
H29A—C29—H29C109.5C71—C73—H73A109.5
H29B—C29—H29C109.5C71—C73—H73B109.5
N24—C30—C31113.1 (3)H73A—C73—H73B109.5
N24—C30—H30A109C71—C73—H73C109.5
C31—C30—H30A109H73A—C73—H73C109.5
N24—C30—H30B109H73B—C73—H73C109.5
C31—C30—H30B109C71—C74—H74A109.5
H30A—C30—H30B107.8C71—C74—H74B109.5
C34—C31—C32108.5 (4)H74A—C74—H74B109.5
C34—C31—C30109.5 (4)C71—C74—H74C109.5
C32—C31—C30108.4 (4)H74A—C74—H74C109.5
C34—C31—C33110.1 (5)H74B—C74—H74C109.5
C32—C31—C33110.9 (4)C82—O81—C86119.8 (3)
C30—C31—C33109.5 (4)O95—C82—N83123.3 (4)
C31—C32—H32A109.5O95—C82—O81118.1 (4)
C31—C32—H32B109.5N83—C82—O81118.6 (4)
H32A—C32—H32B109.5C82—N83—N84125.2 (3)
C31—C32—H32C109.5C82—N83—H83115 (3)
H32A—C32—H32C109.5N84—N83—H83118 (3)
H32B—C32—H32C109.5N83—N84—C85108.3 (3)
C31—C33—H33A109.5N83—N84—C90110.5 (3)
C31—C33—H33B109.5C85—N84—C90113.6 (3)
H33A—C33—H33B109.5N84—C85—C86107.9 (3)
C31—C33—H33C109.5N84—C85—C87111.1 (3)
H33A—C33—H33C109.5C86—C85—C87115.0 (4)
H33B—C33—H33C109.5N84—C85—H85107.5
C31—C34—H34A109.5C86—C85—H85107.5
C31—C34—H34B109.5C87—C85—H85107.5
H34A—C34—H34B109.5O81—C86—C85111.4 (3)
C31—C34—H34C109.5O81—C86—H86A109.3
H34A—C34—H34C109.5C85—C86—H86A109.3
H34B—C34—H34C109.5O81—C86—H86B109.3
C42—O41—C46119.1 (3)C85—C86—H86B109.3
O55—C42—N43122.5 (4)H86A—C86—H86B108
O55—C42—O41118.0 (3)C89—C87—C88109.1 (4)
N43—C42—O41119.6 (3)C89—C87—C85110.7 (4)
C42—N43—N44125.8 (3)C88—C87—C85113.0 (4)
C42—N43—H43117 (2)C89—C87—H87108
N44—N43—H43113 (2)C88—C87—H87108
N43—N44—C45108.2 (3)C85—C87—H87108
N43—N44—C50111.2 (4)C87—C88—H88A109.5
C45—N44—C50114.5 (3)C87—C88—H88B109.5
N44—C45—C46108.4 (3)H88A—C88—H88B109.5
N44—C45—C47110.2 (3)C87—C88—H88C109.5
C46—C45—C47116.0 (4)H88A—C88—H88C109.5
N44—C45—H45107.3H88B—C88—H88C109.5
C46—C45—H45107.3C87—C89—H89A109.5
C47—C45—H45107.3C87—C89—H89B109.5
O41—C46—C45109.6 (3)H89A—C89—H89B109.5
O41—C46—H46A109.7C87—C89—H89C109.5
C45—C46—H46A109.7H89A—C89—H89C109.5
O41—C46—H46B109.7H89B—C89—H89C109.5
C45—C46—H46B109.7N84—C90—C91114.5 (3)
H46A—C46—H46B108.2N84—C90—H90A108.6
C48—C47—C45112.4 (5)C91—C90—H90A108.6
C48—C47—C49110.1 (5)N84—C90—H90B108.6
C45—C47—C49111.6 (4)C91—C90—H90B108.6
C48—C47—H47107.5H90A—C90—H90B107.6
C45—C47—H47107.5C93—C91—C90112.8 (4)
C49—C47—H47107.5C93—C91—C92111.7 (5)
C47—C48—H48A109.5C90—C91—C92108.6 (4)
C47—C48—H48B109.5C93—C91—C94107.7 (6)
H48A—C48—H48B109.5C90—C91—C94108.8 (4)
C47—C48—H48C109.5C92—C91—C94107.0 (5)
H48A—C48—H48C109.5C91—C92—H92A109.5
H48B—C48—H48C109.5C91—C92—H92B109.5
C47—C49—H49A109.5H92A—C92—H92B109.5
C47—C49—H49B109.5C91—C92—H92C109.5
H49A—C49—H49B109.5H92A—C92—H92C109.5
C47—C49—H49C109.5H92B—C92—H92C109.5
H49A—C49—H49C109.5C91—C93—H93A109.5
H49B—C49—H49C109.5C91—C93—H93B109.5
N44—C50—C51115.2 (4)H93A—C93—H93B109.5
N44—C50—H50A108.5C91—C93—H93C109.5
C51—C50—H50A108.5H93A—C93—H93C109.5
N44—C50—H50B108.5H93B—C93—H93C109.5
C51—C50—H50B108.5C91—C94—H94A109.5
H50A—C50—H50B107.5C91—C94—H94B109.5
C52A—C51—C54B140.4 (13)H94A—C94—H94B109.5
C52A—C51—C50107.3 (8)C91—C94—H94C109.5
C54B—C51—C50106.5 (9)H94A—C94—H94C109.5
C52A—C51—C53A112.6 (9)H94B—C94—H94C109.5
C6—O1—C2—O15−179.7 (4)N44—C45—C47—C48176.2 (5)
C6—O1—C2—N3−1.4 (6)C46—C45—C47—C4852.6 (6)
O15—C2—N3—N4171.3 (4)N44—C45—C47—C49−59.5 (5)
O1—C2—N3—N4−6.9 (7)C46—C45—C47—C49176.8 (4)
C2—N3—N4—C5−20.3 (6)N43—N44—C50—C5181.6 (5)
C2—N3—N4—C10106.3 (5)C45—N44—C50—C51−155.4 (4)
N3—N4—C5—C652.0 (4)N44—C50—C51—C52A−86.4 (8)
C10—N4—C5—C6−72.6 (4)N44—C50—C51—C54B72.6 (10)
N3—N4—C5—C7−75.3 (4)N44—C50—C51—C53A151.8 (8)
C10—N4—C5—C7160.1 (3)N44—C50—C51—C52B−52.1 (10)
C2—O1—C6—C535.1 (5)N44—C50—C51—C54A32.0 (9)
N4—C5—C6—O1−61.2 (4)N44—C50—C51—C53B−168.8 (9)
C7—C5—C6—O163.5 (4)C66—O61—C62—O75−178.0 (4)
N4—C5—C7—C9−60.6 (4)C66—O61—C62—N631.6 (6)
C6—C5—C7—C9176.0 (4)O75—C62—N63—N64178.0 (4)
N4—C5—C7—C8175.9 (3)O61—C62—N63—N64−1.5 (6)
C6—C5—C7—C852.6 (5)C62—N63—N64—C7097.4 (4)
N3—N4—C10—C11118.9 (4)C62—N63—N64—C65−28.1 (5)
C5—N4—C10—C11−118.5 (4)N63—N64—C65—C6654.1 (4)
N4—C10—C11—C1462.7 (4)C70—N64—C65—C66−70.2 (4)
N4—C10—C11—C13−59.7 (4)N63—N64—C65—C67−72.5 (4)
N4—C10—C11—C12−179.0 (3)C70—N64—C65—C67163.2 (3)
C26—O21—C22—O35177.6 (4)C62—O61—C66—C6528.0 (6)
C26—O21—C22—N23−6.0 (6)N64—C65—C66—O61−56.3 (4)
O35—C22—N23—N24173.1 (4)C67—C65—C66—O6168.0 (4)
O21—C22—N23—N24−3.2 (6)N64—C65—C67—C69−48.6 (5)
C22—N23—N24—C25−21.1 (5)C66—C65—C67—C69−171.5 (4)
C22—N23—N24—C30104.9 (5)N64—C65—C67—C68−172.3 (4)
N23—N24—C25—C2650.9 (4)C66—C65—C67—C6864.8 (5)
C30—N24—C25—C26−73.1 (4)N63—N64—C70—C71105.7 (4)
N23—N24—C25—C27−75.6 (4)C65—N64—C70—C71−132.2 (4)
C30—N24—C25—C27160.5 (3)N64—C70—C71—C73−61.7 (6)
C22—O21—C26—C2537.7 (5)N64—C70—C71—C72176.7 (4)
N24—C25—C26—O21−60.8 (4)N64—C70—C71—C7461.0 (6)
C27—C25—C26—O2164.0 (4)C86—O81—C82—O95−175.7 (4)
N24—C25—C27—C29−57.2 (4)C86—O81—C82—N833.1 (6)
C26—C25—C27—C29179.3 (4)O95—C82—N83—N84178.4 (4)
N24—C25—C27—C28−179.8 (3)O81—C82—N83—N84−0.4 (6)
C26—C25—C27—C2856.8 (5)C82—N83—N84—C85−31.3 (5)
N23—N24—C30—C31120.1 (4)C82—N83—N84—C9093.7 (4)
C25—N24—C30—C31−117.4 (4)N83—N84—C85—C8656.7 (4)
N24—C30—C31—C3461.6 (5)C90—N84—C85—C86−66.5 (4)
N24—C30—C31—C32179.8 (4)N83—N84—C85—C87−70.3 (4)
N24—C30—C31—C33−59.2 (5)C90—N84—C85—C87166.5 (3)
C46—O41—C42—O55−178.8 (4)C82—O81—C86—C8525.6 (6)
C46—O41—C42—N431.0 (6)N84—C85—C86—O81−55.8 (4)
O55—C42—N43—N44174.1 (4)C87—C85—C86—O8168.9 (4)
O41—C42—N43—N44−5.7 (6)N84—C85—C87—C89−54.8 (5)
C42—N43—N44—C45−23.6 (5)C86—C85—C87—C89−177.8 (4)
C42—N43—N44—C50102.9 (5)N84—C85—C87—C88−177.5 (4)
N43—N44—C45—C4654.1 (4)C86—C85—C87—C8859.5 (5)
C50—N44—C45—C46−70.5 (4)N83—N84—C90—C9191.5 (4)
N43—N44—C45—C47−73.9 (4)C85—N84—C90—C91−146.5 (4)
C50—N44—C45—C47161.6 (4)N84—C90—C91—C93−55.0 (6)
C42—O41—C46—C4531.4 (5)N84—C90—C91—C92−179.4 (4)
N44—C45—C46—O41−59.2 (5)N84—C90—C91—C9464.5 (5)
C47—C45—C46—O4165.3 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N23—H23···O55i0.78 (4)2.16 (4)2.937 (5)177 (5)
N43—H43···O35ii0.88 (4)1.99 (4)2.868 (5)175 (3)
N63—H63···O95iii0.84 (4)2.13 (4)2.949 (5)163 (3)
N83—H83···O75iv0.89 (4)2.04 (4)2.926 (4)175 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2318).

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