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ISSN: 2056-9890

(1S,3S,4S)-tert-Butyl N-[1-benzyl-3-hydr­­oxy-5-phenyl-4-(picolinamido)pent­yl]carbamate

aDepartment of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China
*Correspondence e-mail: zjf485@xmu.edu.cn

(Received 4 June 2008; accepted 23 June 2008; online 28 June 2008)

The title compound, C29H35N3O4, was obtained by the reaction of (2S,4S,5S)-tert-butyl N-(4-amino-1-benzyl-3-hydr­oxy-5-phenyl­pent­yl)carbamate and picolinic acid using oxalyl chloride as a chlorinating reagent to activate the carboxyl group. In the crystal structure there are two mol­ecules in the asymmetric unit, which are aligned edge-to-face. In one mol­ecule, the pyridyl ring forms a dihedral angle of 22.0 (1)° with the phenyl ring of the terminal benzyl group and 14.3 (1)° with the other phenyl ring; in the other mol­ecule, the corresponding angles are 12.1 (1) and 10.6 (1)°, respectively. The packing is stabilized by inter­molecular hydrogen bonds and C—H⋯π inter­actions.

Related literature

For related literature, see: Nishiyama et al. (1989[Nishiyama, H., Sakaguchi, H., Nakamura, T., HoriHata, M., Kondo, M. & Itoh, K. (1989). Organometallics, 8, 846-848.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Pavel et al. (1993[Pavel, H., Heinrich, L. S. & Edward, W. S. (1993). J. Am. Chem. Soc. 116, 3500-3506.]).

[Scheme 1]

Experimental

Crystal data
  • C29H35N3O4

  • Mr = 489.60

  • Monoclinic, P 21

  • a = 11.7573 (12) Å

  • b = 15.9783 (18) Å

  • c = 15.0881 (15) Å

  • β = 103.787 (9)°

  • V = 2752.8 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 (2) K

  • 0.70 × 0.32 × 0.12 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.991

  • 14395 measured reflections

  • 4903 independent reflections

  • 3396 reflections with I > 2σ(I)

  • Rint = 0.070

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.180

  • S = 1.19

  • 4903 reflections

  • 649 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2AA⋯O2B 0.88 2.04 2.888 (5) 162
O1A—H1AB⋯O3B 0.84 1.89 2.707 (5) 164
N2B—H2BA⋯O2Ai 0.88 2.01 2.843 (5) 159
O1B—H1BB⋯O3Ai 0.84 1.88 2.711 (5) 171
C23B—H23B⋯CgAii 0.95 2.97 3.776 (4) 144
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]. CgA is the centroid of the C6–C11 phenyl ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, (1), is a key intermediate for the preparation of recycling chiral ligands, such as oxazoline ligands for asymmetric catalysts. The majority of the syntheses of these ligands have followed a general synthetic route in which acids were first condensed with the corresponding optically active β-aminoalcohols to form the hydroxyamide derivatives. The hydoxy groups in the hydroxyamides were then activated and the resulting intermediates were cyclized to provide the oxazoline ligands (Nishiyama et al., 1989).

The title compound was obtained by the reaction of (2S,4S,5S)-tert-butyl N-(4-amino-1-benzyl-3-hydroxy-5-phenylpentyl)carbamate and picolinic acid using oxalyl chloride as a chlorinating reagent to activate the carboxyl group. An X-ray crystal structure determination was carried out to determine its conformation. Bond lengths are in agreement with values reported in the literature (Allen et al., 1987).

In the crystal structure of (1), there are two molecules in the asymmetric unit (Fig. 1). In molecule A, the dihedral angle of the pyridyl and the C6A/C11A phenyl rings is 22.0 (1)° and for the pyridyl and C13A/C18A rings it is 14.3 (1)°. In molecule B the angles are 12.1 (1)° and 10.6 (1)° respectively. The packing is shown in Fig. 2. Molecules are linked by O—H···O and N—H···O hydrogen bonds involving all the potential donors, generating linear chains parallel to the a axis. The packing is further stablized by C—H···π interactions, with typical geometry (Pavel et al., 1993).

Related literature top

For related literature, see: Nishiyama et al. (1989); Allen et al. (1987); Pavel et al. (1993). CgA is the centroid of the C6–C11 phenyl ring.

Experimental top

Picolinic acid (0.38 g, 3.12 mmol) was suspended in dichloromethane (40 ml) at 273 K. N,N-Dimethylformamide (0.1 ml) and oxalyl chloride (0.27 ml, 3.12 mmol) in dichloromethane (10 ml) were added and stirred for 3 h. The reaction mixture was then cooled to 263 K, (2S,4S,5S)-tert-butyl N-(4-amino-1-benzyl-3-hydroxy-5-phenylpentyl)carbamate (1.00 g, 2.60 mmol) and triethylamine (2.2 ml, 15.60 mmol) in dichloromethane (10 ml) were added dropwise and the mixture was stirred at 273 K. After 0.5 h, the reaction mixture was quenched with water (15 ml). The inorganic layer was separated followed by extraction with dichloromethane. The organic phases were combined and dried over anhydrous MgSO4 and concentrated in vacuo, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether 1:2), giving the product (1.89 g, 98.2%) as a white solid. Single crystals were obtained by slow evaporation of a solution in ethyl acetate/dichloromethane.

Refinement top

The hydrogen atoms were positioned geometrically (C—H = 0.93, 0.98, 0.97 or 0.96Å for phenyl, tertiary, methylene or methyl H atoms respectively) and were included in the refinement in the riding model approximation. The displacement parameters of methyl H atoms were set to 1.5Ueq(C), while those of other H atoms were set to 1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs were merged; the absolute configuration was assumed from the synthesis.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (1) with the atom-labelling scheme, showing 50% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the molecules, viewed down the a axis. C—H···π interactions and hydrogen bonds are shown as dashed lines. Cg is the centroid of the C6/C11 phenyl ring.
(1S,3S,4S)-tert-Butyl N-[1-benzyl-3-hydroxy-5-phenyl-4-(picolinamido)pentyl]carbamate top
Crystal data top
C29H35N3O4F(000) = 1048
Mr = 489.60Dx = 1.181 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3695 reflections
a = 11.7573 (12) Åθ = 4.1–32.7°
b = 15.9783 (18) ŵ = 0.08 mm1
c = 15.0881 (15) ÅT = 173 K
β = 103.787 (9)°Needle, colorless
V = 2752.8 (5) Å30.70 × 0.32 × 0.12 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
4903 independent reflections
Radiation source: fine-focus sealed tube3396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
Detector resolution: 16.1903 pixels mm-1θmax = 26.0°, θmin = 4.1°
ϕ and ω scansh = 1314
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1915
Tmin = 0.947, Tmax = 0.991l = 1818
14395 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.180 w = 1/[σ2(Fo2) + (0.0854P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max = 0.175
4903 reflectionsΔρmax = 0.30 e Å3
649 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: indeterminate
Primary atom site location: structure-invariant direct methods
Crystal data top
C29H35N3O4V = 2752.8 (5) Å3
Mr = 489.60Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.7573 (12) ŵ = 0.08 mm1
b = 15.9783 (18) ÅT = 173 K
c = 15.0881 (15) Å0.70 × 0.32 × 0.12 mm
β = 103.787 (9)°
Data collection top
Bruker APEX CCD
diffractometer
4903 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
3396 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.991Rint = 0.071
14395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.180(Δ/σ)max = 0.175
S = 1.19Δρmax = 0.30 e Å3
4903 reflectionsΔρmin = 0.29 e Å3
649 parametersAbsolute structure: indeterminate
1 restraint
Special details top

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
N1A0.2331 (3)0.0359 (3)0.0924 (2)0.0313 (10)
H1AA0.28480.01930.06250.038*
O1A0.4696 (3)0.0739 (2)0.1582 (3)0.0478 (10)
H1AB0.51430.03520.15000.072*
C1A0.2764 (4)0.0785 (3)0.1767 (3)0.0318 (12)
H1AC0.22580.06360.21910.038*
N1B0.8118 (3)0.0620 (3)0.4204 (3)0.0342 (11)
H1BA0.88360.05800.45450.041*
O1B0.9973 (3)0.1330 (2)0.3547 (2)0.0479 (10)
H1BB1.05510.10060.36870.072*
C1B0.7958 (4)0.1055 (3)0.3347 (3)0.0349 (13)
H1BC0.72620.08100.29110.042*
N2A0.3736 (3)0.0516 (3)0.3814 (2)0.0348 (11)
H2AA0.44950.04520.40300.042*
O2A0.0392 (3)0.0395 (3)0.0893 (2)0.0478 (10)
C2A0.4011 (4)0.0460 (3)0.2178 (3)0.0333 (12)
H2AB0.43130.07230.27900.040*
N2B0.8151 (3)0.0182 (3)0.1264 (2)0.0356 (11)
H2BA0.87430.02220.10030.043*
O2B0.6237 (3)0.0297 (3)0.4112 (2)0.0475 (10)
C2B0.9034 (4)0.0912 (3)0.2963 (3)0.0316 (12)
H2BB0.88860.11870.23500.038*
N3A0.1977 (3)0.0567 (3)0.0578 (3)0.0422 (12)
O3A0.1966 (3)0.0426 (3)0.4110 (2)0.0495 (10)
C3A0.4070 (4)0.0499 (3)0.2284 (3)0.0316 (12)
H3AB0.48920.06650.25490.038*
H3AC0.38230.07590.16730.038*
N3B0.8810 (4)0.0150 (3)0.5801 (3)0.0378 (11)
O3B0.6284 (3)0.0286 (3)0.1105 (2)0.0445 (10)
C3B0.9265 (4)0.0007 (3)0.2838 (3)0.0328 (12)
H3BB0.99780.00570.26020.039*
H3BC0.94290.02810.34440.039*
O4A0.3605 (3)0.0011 (2)0.5138 (2)0.0419 (10)
C4A0.3306 (4)0.0835 (3)0.2884 (3)0.0299 (12)
H4AA0.24960.06120.26440.036*
O4B0.7190 (3)0.0316 (2)0.0065 (2)0.0403 (10)
C4B0.8286 (4)0.0475 (3)0.2206 (3)0.0334 (12)
H4BA0.75430.03480.23920.040*
C5A0.3234 (5)0.1790 (3)0.2860 (3)0.0387 (14)
H5AA0.40370.20190.29590.046*
H5AB0.29050.19820.33710.046*
C5B0.8470 (5)0.1415 (3)0.2263 (4)0.0410 (14)
H5BA0.78710.16870.17740.049*
H5BB0.92480.15470.21540.049*
C6A0.2490 (4)0.2143 (3)0.1971 (3)0.0332 (13)
C6B0.8397 (5)0.1770 (3)0.3158 (4)0.0420 (15)
C7A0.1329 (5)0.1966 (4)0.1733 (4)0.0514 (17)
H7AA0.09930.16230.21170.062*
C7B0.7332 (5)0.1716 (4)0.3433 (4)0.0501 (16)
H7BA0.66610.14760.30360.060*
C8A0.0632 (5)0.2281 (4)0.0934 (4)0.0578 (19)
H8AA0.01840.21660.07760.069*
C8B0.7267 (5)0.2011 (4)0.4276 (4)0.0528 (16)
H8BA0.65470.19770.44560.063*
C9A0.1127 (6)0.2765 (5)0.0365 (4)0.068 (2)
H9AA0.06650.29610.02010.082*
C9B0.8228 (6)0.2352 (4)0.4859 (4)0.0584 (18)
H9BA0.81840.25460.54450.070*
C10A0.2263 (6)0.2954 (5)0.0624 (5)0.070 (2)
H10A0.25910.33190.02540.084*
C10B0.9243 (6)0.2409 (4)0.4588 (4)0.0608 (19)
H10B0.99000.26750.49750.073*
C11A0.2988 (5)0.2629 (4)0.1423 (4)0.0520 (17)
H11A0.38040.27440.15800.062*
C11B0.9343 (5)0.2095 (4)0.3775 (4)0.0481 (16)
H11B1.00860.21010.36290.058*
C120.2726 (5)0.1747 (3)0.1633 (4)0.0395 (14)
H12A0.19240.19110.13040.047*
H12B0.32640.19020.12460.047*
C12B0.7716 (5)0.1984 (3)0.3468 (3)0.0363 (13)
H12C0.70170.20370.37210.044*
H12D0.83890.22280.39160.044*
C13A0.3058 (5)0.2229 (3)0.2508 (4)0.0370 (13)
C13B0.7517 (5)0.2480 (3)0.2595 (3)0.0354 (13)
C14A0.4198 (5)0.2501 (4)0.2874 (4)0.0506 (17)
H14A0.47930.23600.25710.061*
C14B0.8367 (5)0.2968 (4)0.2404 (4)0.0475 (15)
H14B0.91050.29890.28310.057*
C15A0.4486 (5)0.2965 (4)0.3657 (5)0.0576 (19)
H15A0.52670.31530.38860.069*
C15B0.8209 (6)0.3437 (4)0.1615 (5)0.0633 (19)
H15B0.88270.37670.14950.076*
C16A0.3615 (6)0.3159 (4)0.4118 (4)0.0626 (19)
H16A0.38020.34730.46690.075*
C16B0.7146 (6)0.3412 (4)0.1015 (4)0.0562 (17)
H16B0.70230.37380.04740.067*
C17A0.2508 (6)0.2896 (5)0.3770 (5)0.072 (2)
H17A0.19120.30290.40750.086*
C17B0.6229 (6)0.2924 (4)0.1168 (4)0.0524 (17)
H17B0.54900.29150.07420.063*
C18A0.2234 (5)0.2434 (4)0.2970 (4)0.0528 (17)
H18A0.14490.22550.27370.063*
C18B0.6428 (5)0.2452 (3)0.1963 (3)0.0401 (14)
H18B0.58220.21060.20790.048*
C19A0.1186 (4)0.0190 (3)0.0544 (3)0.0348 (13)
C19B0.7258 (4)0.0274 (3)0.4519 (3)0.0321 (12)
C20A0.1030 (5)0.0318 (3)0.0288 (3)0.0388 (13)
C20B0.7662 (4)0.0140 (3)0.5421 (3)0.0356 (13)
C21A0.0087 (5)0.0509 (4)0.0795 (4)0.0460 (15)
H21A0.07550.03360.05920.055*
C21B0.6835 (5)0.0504 (4)0.5833 (3)0.0439 (15)
H21B0.60210.04690.55580.053*
C22A0.0218 (6)0.0954 (5)0.1598 (4)0.065 (2)
H22A0.09760.10860.19580.078*
C22B0.7245 (5)0.0917 (4)0.6658 (4)0.0492 (16)
H22B0.67120.11860.69490.059*
C23A0.0758 (6)0.1200 (4)0.1864 (4)0.062 (2)
H23A0.06930.15030.24160.075*
C23B0.8396 (6)0.0934 (4)0.7039 (4)0.0540 (17)
H23B0.86890.12120.76040.065*
C24A0.1823 (6)0.1005 (4)0.1331 (4)0.0546 (17)
H24A0.24980.11980.15130.066*
C24B0.9165 (5)0.0533 (4)0.6590 (4)0.0535 (17)
H24B0.99790.05390.68700.064*
C25A0.3027 (4)0.0322 (3)0.4336 (3)0.0289 (12)
C25B0.7128 (5)0.0147 (3)0.0796 (3)0.0360 (13)
C26A0.2951 (5)0.0291 (4)0.5801 (3)0.0420 (14)
C26B0.6116 (4)0.0549 (3)0.0752 (3)0.0355 (13)
C27A0.2377 (7)0.0439 (5)0.6154 (5)0.081 (2)
H27A0.17560.06660.56600.122*
H27B0.29630.08750.63760.122*
H27C0.20400.02520.66550.122*
C27B0.5242 (6)0.0143 (5)0.0854 (4)0.066 (2)
H27D0.49340.01730.03050.099*
H27E0.56200.06740.09350.099*
H27F0.45970.00350.13870.099*
C28A0.2088 (6)0.0947 (5)0.5389 (5)0.064 (2)
H28A0.14570.06940.49220.096*
H28B0.17590.12000.58650.096*
H28C0.24790.13790.51090.096*
C28B0.6612 (6)0.0607 (4)0.1606 (4)0.0573 (18)
H28D0.71830.10640.15300.086*
H28E0.59720.07160.21420.086*
H28F0.69950.00780.16890.086*
C29A0.3931 (6)0.0683 (5)0.6525 (4)0.068 (2)
H29A0.42700.11530.62580.102*
H29B0.36150.08860.70310.102*
H29C0.45380.02630.67520.102*
C29B0.5680 (6)0.1377 (4)0.0535 (4)0.0627 (19)
H29D0.53680.13290.00100.094*
H29E0.50580.15680.10500.094*
H29F0.63240.17820.04210.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0250 (19)0.039 (2)0.030 (2)0.0001 (19)0.0074 (16)0.0064 (19)
O1A0.0418 (18)0.041 (2)0.072 (2)0.0081 (18)0.0353 (17)0.0130 (18)
C1A0.034 (2)0.039 (3)0.029 (2)0.007 (2)0.0193 (19)0.006 (2)
N1B0.033 (2)0.038 (2)0.031 (2)0.003 (2)0.0072 (17)0.0077 (18)
O1B0.046 (2)0.037 (2)0.056 (2)0.0089 (19)0.0041 (17)0.0084 (19)
C1B0.044 (3)0.040 (3)0.021 (2)0.005 (2)0.008 (2)0.005 (2)
N2A0.031 (2)0.044 (3)0.028 (2)0.003 (2)0.0037 (16)0.0090 (19)
O2A0.0287 (17)0.072 (3)0.0445 (19)0.0030 (19)0.0115 (15)0.012 (2)
C2A0.046 (3)0.028 (3)0.030 (2)0.003 (2)0.017 (2)0.002 (2)
N2B0.033 (2)0.049 (3)0.024 (2)0.002 (2)0.0053 (16)0.0062 (19)
O2B0.0439 (19)0.067 (3)0.0333 (18)0.007 (2)0.0122 (15)0.0144 (18)
C2B0.035 (3)0.033 (3)0.025 (2)0.004 (2)0.003 (2)0.008 (2)
N3A0.033 (2)0.049 (3)0.042 (2)0.004 (2)0.0058 (18)0.010 (2)
O3A0.041 (2)0.069 (3)0.0417 (19)0.007 (2)0.0155 (15)0.0246 (19)
C3A0.034 (2)0.032 (3)0.029 (2)0.005 (2)0.0075 (19)0.005 (2)
N3B0.040 (2)0.038 (3)0.035 (2)0.000 (2)0.0076 (18)0.0049 (19)
O3B0.0330 (17)0.063 (3)0.0386 (18)0.0011 (19)0.0106 (15)0.0039 (18)
C3B0.038 (3)0.036 (3)0.027 (2)0.001 (2)0.012 (2)0.000 (2)
O4A0.0332 (17)0.061 (3)0.0329 (17)0.0042 (18)0.0101 (14)0.0114 (17)
C4A0.033 (3)0.030 (3)0.024 (2)0.004 (2)0.002 (2)0.005 (2)
O4B0.0402 (18)0.055 (2)0.0234 (16)0.0034 (18)0.0040 (14)0.0030 (17)
C4B0.041 (3)0.028 (3)0.032 (2)0.000 (2)0.009 (2)0.003 (2)
C5A0.058 (3)0.032 (3)0.025 (3)0.003 (3)0.008 (2)0.003 (2)
C5B0.045 (3)0.033 (3)0.041 (3)0.006 (3)0.002 (2)0.003 (2)
C6A0.039 (3)0.031 (3)0.033 (3)0.009 (2)0.015 (2)0.003 (2)
C6B0.056 (3)0.031 (3)0.036 (3)0.002 (3)0.003 (2)0.001 (2)
C7A0.055 (4)0.052 (4)0.049 (3)0.003 (3)0.016 (3)0.007 (3)
C7B0.047 (3)0.043 (3)0.059 (4)0.010 (3)0.008 (3)0.000 (3)
C8A0.045 (3)0.061 (4)0.060 (4)0.011 (3)0.004 (3)0.005 (3)
C8B0.060 (3)0.043 (3)0.064 (4)0.006 (3)0.031 (3)0.001 (3)
C9A0.074 (4)0.076 (5)0.048 (4)0.015 (4)0.002 (3)0.017 (4)
C9B0.093 (5)0.042 (4)0.042 (3)0.012 (4)0.019 (3)0.008 (3)
C10A0.070 (4)0.070 (5)0.062 (4)0.011 (4)0.001 (3)0.029 (4)
C10B0.069 (4)0.060 (4)0.050 (4)0.014 (4)0.008 (3)0.009 (3)
C11A0.050 (3)0.061 (4)0.045 (3)0.009 (3)0.009 (3)0.015 (3)
C11B0.050 (3)0.044 (3)0.049 (3)0.003 (3)0.011 (3)0.009 (3)
C120.044 (3)0.035 (3)0.044 (3)0.005 (3)0.018 (2)0.004 (2)
C12B0.040 (3)0.032 (3)0.036 (3)0.008 (2)0.005 (2)0.003 (2)
C13A0.043 (3)0.022 (3)0.045 (3)0.003 (2)0.009 (2)0.000 (2)
C13B0.047 (3)0.025 (3)0.037 (3)0.007 (2)0.014 (2)0.002 (2)
C14A0.049 (3)0.042 (3)0.057 (4)0.003 (3)0.007 (3)0.003 (3)
C14B0.048 (3)0.038 (3)0.060 (3)0.000 (3)0.020 (3)0.005 (3)
C15A0.042 (3)0.038 (3)0.084 (5)0.004 (3)0.002 (3)0.004 (3)
C15B0.059 (4)0.049 (4)0.090 (5)0.002 (3)0.034 (3)0.010 (4)
C16A0.081 (5)0.046 (4)0.057 (4)0.016 (4)0.009 (3)0.010 (3)
C16B0.095 (4)0.036 (3)0.048 (3)0.011 (3)0.039 (3)0.012 (3)
C17A0.058 (4)0.071 (5)0.094 (5)0.004 (4)0.033 (4)0.031 (4)
C17B0.066 (4)0.044 (3)0.046 (3)0.008 (3)0.010 (3)0.002 (3)
C18A0.051 (3)0.050 (4)0.063 (4)0.007 (3)0.024 (3)0.019 (3)
C18B0.048 (3)0.034 (3)0.038 (3)0.003 (3)0.009 (2)0.006 (2)
C19A0.039 (3)0.034 (3)0.031 (3)0.000 (3)0.007 (2)0.008 (2)
C19B0.029 (2)0.036 (3)0.032 (2)0.004 (2)0.010 (2)0.001 (2)
C20A0.052 (3)0.036 (3)0.030 (2)0.002 (3)0.013 (2)0.001 (2)
C20B0.033 (3)0.037 (3)0.037 (3)0.002 (3)0.009 (2)0.001 (2)
C21A0.035 (3)0.057 (4)0.043 (3)0.001 (3)0.004 (2)0.012 (3)
C21B0.047 (3)0.051 (4)0.037 (3)0.006 (3)0.017 (2)0.012 (3)
C22A0.058 (4)0.079 (5)0.052 (4)0.005 (4)0.000 (3)0.022 (4)
C22B0.056 (4)0.046 (3)0.049 (3)0.004 (3)0.021 (3)0.004 (3)
C23A0.080 (4)0.066 (5)0.043 (3)0.005 (4)0.018 (3)0.019 (3)
C23B0.080 (4)0.045 (3)0.037 (3)0.004 (3)0.014 (3)0.009 (3)
C24A0.058 (3)0.062 (4)0.049 (3)0.013 (3)0.021 (3)0.024 (3)
C24B0.056 (4)0.061 (4)0.040 (3)0.008 (3)0.004 (3)0.010 (3)
C25A0.029 (2)0.032 (3)0.027 (2)0.009 (2)0.0085 (19)0.001 (2)
C25B0.041 (3)0.034 (3)0.033 (3)0.004 (3)0.009 (2)0.006 (2)
C26A0.050 (3)0.048 (3)0.030 (3)0.018 (3)0.014 (2)0.006 (2)
C26B0.035 (3)0.034 (3)0.030 (2)0.001 (3)0.008 (2)0.008 (2)
C27A0.122 (5)0.081 (5)0.062 (4)0.013 (5)0.064 (4)0.007 (4)
C27B0.069 (4)0.062 (5)0.061 (4)0.012 (4)0.006 (3)0.002 (3)
C28A0.072 (4)0.058 (4)0.057 (4)0.022 (4)0.006 (3)0.013 (3)
C28B0.071 (4)0.064 (4)0.033 (3)0.008 (4)0.005 (3)0.003 (3)
C29A0.060 (4)0.104 (6)0.037 (3)0.018 (4)0.003 (3)0.025 (3)
C29B0.075 (4)0.056 (4)0.056 (4)0.010 (4)0.013 (3)0.007 (3)
Geometric parameters (Å, º) top
N1A—C19A1.360 (6)C10B—H10B0.950
N1A—C1A1.425 (6)C11A—H11A0.950
N1A—H1AA0.880C11B—H11B0.950
O1A—C2A1.414 (6)C12—C13A1.498 (7)
O1A—H1AB0.840C12—H12A0.990
C1A—C2A1.539 (7)C12—H12B0.990
C1A—C121.549 (7)C12B—C13B1.506 (7)
C1A—H1AC1.000C12B—H12C0.990
N1B—C19B1.336 (6)C12B—H12D0.990
N1B—C1B1.440 (6)C13A—C18A1.361 (8)
N1B—H1BA0.880C13A—C14A1.392 (8)
O1B—C2B1.407 (6)C13B—C14B1.351 (8)
O1B—H1BB0.840C13B—C18B1.404 (7)
C1B—C12B1.531 (7)C14A—C15A1.367 (9)
C1B—C2B1.529 (7)C14A—H14A0.950
C1B—H1BC1.000C14B—C15B1.382 (9)
N2A—C25A1.314 (6)C14B—H14B0.950
N2A—C4A1.464 (6)C15A—C16A1.404 (10)
N2A—H2AA0.880C15A—H15A0.950
O2A—C19A1.220 (6)C15B—C16B1.358 (9)
C2A—C3A1.542 (7)C15B—H15B0.950
C2A—H2AB1.000C16A—C17A1.349 (9)
N2B—C25B1.348 (6)C16A—H16A0.950
N2B—C4B1.467 (6)C16B—C17B1.393 (9)
N2B—H2BA0.880C16B—H16B0.950
O2B—C19B1.212 (5)C17A—C18A1.387 (9)
C2B—C3B1.513 (7)C17A—H17A0.950
C2B—H2BB1.000C17B—C18B1.388 (8)
N3A—C24A1.310 (7)C17B—H17B0.950
N3A—C20A1.349 (7)C18A—H18A0.950
O3A—C25A1.223 (6)C18B—H18B0.950
C3A—C4A1.518 (7)C19A—C20A1.470 (7)
C3A—H3AB0.990C19B—C20B1.486 (7)
C3A—H3AC0.990C20A—C21A1.387 (7)
N3B—C24B1.315 (7)C20B—C21B1.399 (8)
N3B—C20B1.335 (6)C21A—C22A1.382 (8)
O3B—C25B1.213 (6)C21A—H21A0.950
C3B—C4B1.507 (7)C21B—C22B1.389 (8)
C3B—H3BB0.990C21B—H21B0.950
C3B—H3BC0.990C22A—C23A1.361 (9)
O4A—C25A1.335 (5)C22A—H22A0.950
O4A—C26A1.481 (6)C22B—C23B1.339 (9)
C4A—C5A1.528 (7)C22B—H22B0.950
C4A—H4AA1.000C23A—C24A1.354 (9)
O4B—C25B1.346 (6)C23A—H23A0.950
O4B—C26B1.478 (5)C23B—C24B1.406 (9)
C4B—C5B1.518 (7)C23B—H23B0.950
C4B—H4BA1.000C24A—H24A0.950
C5A—C6A1.525 (7)C24B—H24B0.950
C5A—H5AA0.990C26A—C28A1.488 (8)
C5A—H5AB0.990C26A—C27A1.507 (10)
C5B—C6B1.485 (8)C26A—C29A1.520 (8)
C5B—H5BA0.990C26B—C29B1.484 (9)
C5B—H5BB0.990C26B—C27B1.493 (9)
C6A—C7A1.356 (8)C26B—C28B1.538 (8)
C6A—C11A1.363 (8)C27A—H27A0.980
C6B—C11B1.371 (8)C27A—H27B0.980
C6B—C7B1.413 (8)C27A—H27C0.980
C7A—C8A1.381 (8)C27B—H27D0.980
C7A—H7AA0.950C27B—H27E0.980
C7B—C8B1.376 (9)C27B—H27F0.980
C7B—H7BA0.950C28A—H28A0.980
C8A—C9A1.382 (10)C28A—H28B0.980
C8A—H8AA0.950C28A—H28C0.980
C8B—C9B1.369 (9)C28B—H28D0.980
C8B—H8BA0.950C28B—H28E0.980
C9A—C10A1.334 (10)C28B—H28F0.980
C9A—H9AA0.950C29A—H29A0.980
C9B—C10B1.354 (9)C29A—H29B0.980
C9B—H9BA0.950C29A—H29C0.980
C10A—C11A1.400 (8)C29B—H29D0.980
C10A—H10A0.950C29B—H29E0.980
C10B—C11B1.355 (9)C29B—H29F0.980
C19A—N1A—C1A125.4 (4)C18A—C13A—C14A117.2 (5)
C19A—N1A—H1AA117.3C18A—C13A—C12120.4 (5)
C1A—N1A—H1AA117.3C14A—C13A—C12122.3 (5)
C2A—O1A—H1AB109.5C14B—C13B—C18B118.3 (5)
N1A—C1A—C2A107.5 (4)C14B—C13B—C12B121.4 (5)
N1A—C1A—C12111.3 (4)C18B—C13B—C12B120.3 (5)
C2A—C1A—C12112.5 (4)C15A—C14A—C13A121.9 (6)
N1A—C1A—H1AC108.5C15A—C14A—H14A119.0
C2A—C1A—H1AC108.5C13A—C14A—H14A119.0
C12—C1A—H1AC108.5C13B—C14B—C15B122.9 (6)
C19B—N1B—C1B124.9 (4)C13B—C14B—H14B118.6
C19B—N1B—H1BA117.6C15B—C14B—H14B118.6
C1B—N1B—H1BA117.5C14A—C15A—C16A119.2 (6)
C2B—O1B—H1BB109.5C14A—C15A—H15A120.4
N1B—C1B—C12B110.4 (4)C16A—C15A—H15A120.4
N1B—C1B—C2B109.0 (4)C16B—C15B—C14B118.1 (6)
C12B—C1B—C2B112.6 (4)C16B—C15B—H15B120.9
N1B—C1B—H1BC108.2C14B—C15B—H15B120.9
C12B—C1B—H1BC108.2C17A—C16A—C15A119.2 (6)
C2B—C1B—H1BC108.2C17A—C16A—H16A120.4
C25A—N2A—C4A122.2 (4)C15A—C16A—H16A120.4
C25A—N2A—H2AA118.9C15B—C16B—C17B122.1 (6)
C4A—N2A—H2AA118.9C15B—C16B—H16B118.9
O1A—C2A—C3A111.1 (4)C17B—C16B—H16B119.0
O1A—C2A—C1A105.7 (4)C16A—C17A—C18A120.5 (7)
C3A—C2A—C1A113.1 (4)C16A—C17A—H17A119.8
O1A—C2A—H2AB108.9C18A—C17A—H17A119.7
C3A—C2A—H2AB108.9C18B—C17B—C16B118.0 (5)
C1A—C2A—H2AB108.9C18B—C17B—H17B121.0
C25B—N2B—C4B120.6 (4)C16B—C17B—H17B121.0
C25B—N2B—H2BA119.7C13A—C18A—C17A121.9 (6)
C4B—N2B—H2BA119.7C13A—C18A—H18A119.1
O1B—C2B—C3B113.6 (4)C17A—C18A—H18A119.1
O1B—C2B—C1B106.7 (4)C17B—C18B—C13B120.5 (5)
C3B—C2B—C1B112.4 (4)C17B—C18B—H18B119.7
O1B—C2B—H2BB107.9C13B—C18B—H18B119.7
C3B—C2B—H2BB107.9O2A—C19A—N1A123.1 (5)
C1B—C2B—H2BB107.9O2A—C19A—C20A124.4 (5)
C24A—N3A—C20A119.0 (5)N1A—C19A—C20A112.3 (5)
C4A—C3A—C2A113.3 (4)O2B—C19B—N1B123.3 (4)
C4A—C3A—H3AB108.9O2B—C19B—C20B122.7 (5)
C2A—C3A—H3AB109.0N1B—C19B—C20B114.0 (4)
C4A—C3A—H3AC108.9N3A—C20A—C21A120.2 (5)
C2A—C3A—H3AC108.9N3A—C20A—C19A119.7 (4)
H3AB—C3A—H3AC107.7C21A—C20A—C19A120.1 (5)
C24B—N3B—C20B117.7 (5)N3B—C20B—C21B122.9 (5)
C4B—C3B—C2B115.3 (4)N3B—C20B—C19B117.9 (4)
C4B—C3B—H3BB108.5C21B—C20B—C19B119.2 (4)
C2B—C3B—H3BB108.4C22A—C21A—C20A119.3 (6)
C4B—C3B—H3BC108.4C22A—C21A—H21A120.3
C2B—C3B—H3BC108.4C20A—C21A—H21A120.4
H3BB—C3B—H3BC107.5C22B—C21B—C20B117.8 (5)
C25A—O4A—C26A120.0 (4)C22B—C21B—H21B121.1
N2A—C4A—C3A109.3 (4)C20B—C21B—H21B121.1
N2A—C4A—C5A112.0 (4)C23A—C22A—C21A118.8 (6)
C3A—C4A—C5A112.1 (4)C23A—C22A—H22A120.6
N2A—C4A—H4AA107.8C21A—C22A—H22A120.6
C3A—C4A—H4AA107.8C23B—C22B—C21B119.6 (6)
C5A—C4A—H4AA107.8C23B—C22B—H22B120.2
C25B—O4B—C26B119.6 (4)C21B—C22B—H22B120.2
N2B—C4B—C3B110.2 (4)C22A—C23A—C24A119.0 (6)
N2B—C4B—C5B110.6 (4)C22A—C23A—H23A120.5
C3B—C4B—C5B112.3 (4)C24A—C23A—H23A120.5
N2B—C4B—H4BA107.9C22B—C23B—C24B118.9 (5)
C3B—C4B—H4BA107.9C22B—C23B—H23B120.6
C5B—C4B—H4BA107.9C24B—C23B—H23B120.5
C4A—C5A—C6A114.0 (4)N3A—C24A—C23A123.7 (6)
C4A—C5A—H5AA108.7N3A—C24A—H24A118.1
C6A—C5A—H5AA108.7C23A—C24A—H24A118.1
C4A—C5A—H5AB108.8N3B—C24B—C23B123.1 (5)
C6A—C5A—H5AB108.7N3B—C24B—H24B118.4
H5AA—C5A—H5AB107.6C23B—C24B—H24B118.5
C6B—C5B—C4B113.1 (4)O3A—C25A—N2A123.4 (4)
C6B—C5B—H5BA108.9O3A—C25A—O4A124.7 (4)
C4B—C5B—H5BA109.0N2A—C25A—O4A111.9 (4)
C6B—C5B—H5BB109.0O3B—C25B—O4B124.9 (4)
C4B—C5B—H5BB109.0O3B—C25B—N2B125.4 (4)
H5BA—C5B—H5BB107.8O4B—C25B—N2B109.7 (4)
C7A—C6A—C11A120.6 (5)C28A—C26A—O4A111.1 (4)
C7A—C6A—C5A119.1 (5)C28A—C26A—C27A112.0 (5)
C11A—C6A—C5A120.3 (5)O4A—C26A—C27A109.5 (5)
C11B—C6B—C7B117.1 (5)C28A—C26A—C29A109.5 (5)
C11B—C6B—C5B123.3 (5)O4A—C26A—C29A101.1 (4)
C7B—C6B—C5B119.4 (5)C27A—C26A—C29A113.1 (5)
C6A—C7A—C8A120.4 (6)O4B—C26B—C29B110.6 (4)
C6A—C7A—H7AA119.8O4B—C26B—C27B109.7 (4)
C8A—C7A—H7AA119.8C29B—C26B—C27B114.7 (5)
C8B—C7B—C6B120.0 (5)O4B—C26B—C28B99.9 (4)
C8B—C7B—H7BA120.0C29B—C26B—C28B110.6 (5)
C6B—C7B—H7BA120.0C27B—C26B—C28B110.3 (5)
C7A—C8A—C9A119.7 (6)C26A—C27A—H27A109.5
C7A—C8A—H8AA120.2C26A—C27A—H27B109.5
C9A—C8A—H8AA120.1H27A—C27A—H27B109.5
C9B—C8B—C7B120.7 (6)C26A—C27A—H27C109.5
C9B—C8B—H8BA119.6H27A—C27A—H27C109.5
C7B—C8B—H8BA119.7H27B—C27A—H27C109.5
C10A—C9A—C8A119.0 (6)C26B—C27B—H27D109.5
C10A—C9A—H9AA120.5C26B—C27B—H27E109.5
C8A—C9A—H9AA120.5H27D—C27B—H27E109.5
C10B—C9B—C8B119.0 (6)C26B—C27B—H27F109.5
C10B—C9B—H9BA120.5H27D—C27B—H27F109.5
C8B—C9B—H9BA120.5H27E—C27B—H27F109.5
C9A—C10A—C11A122.0 (7)C26A—C28A—H28A109.5
C9A—C10A—H10A119.0C26A—C28A—H28B109.5
C11A—C10A—H10A119.0H28A—C28A—H28B109.5
C9B—C10B—C11B121.4 (6)C26A—C28A—H28C109.4
C9B—C10B—H10B119.3H28A—C28A—H28C109.5
C11B—C10B—H10B119.3H28B—C28A—H28C109.5
C6A—C11A—C10A118.2 (6)C26B—C28B—H28D109.5
C6A—C11A—H11A120.9C26B—C28B—H28E109.5
C10A—C11A—H11A120.9H28D—C28B—H28E109.5
C10B—C11B—C6B121.6 (6)C26B—C28B—H28F109.5
C10B—C11B—H11B119.2H28D—C28B—H28F109.5
C6B—C11B—H11B119.2H28E—C28B—H28F109.5
C13A—C12—C1A113.7 (4)C26A—C29A—H29A109.5
C13A—C12—H12A108.8C26A—C29A—H29B109.5
C1A—C12—H12A108.8H29A—C29A—H29B109.5
C13A—C12—H12B108.8C26A—C29A—H29C109.4
C1A—C12—H12B108.8H29A—C29A—H29C109.5
H12A—C12—H12B107.7H29B—C29A—H29C109.5
C13B—C12B—C1B113.6 (4)C26B—C29B—H29D109.5
C13B—C12B—H12C108.8C26B—C29B—H29E109.5
C1B—C12B—H12C108.8H29D—C29B—H29E109.5
C13B—C12B—H12D108.9C26B—C29B—H29F109.5
C1B—C12B—H12D108.8H29D—C29B—H29F109.5
H12C—C12B—H12D107.7H29E—C29B—H29F109.5
C19A—N1A—C1A—C2A151.1 (4)C12—C13A—C14A—C15A177.8 (5)
C19A—N1A—C1A—C1285.3 (6)C18B—C13B—C14B—C15B0.0 (9)
C19B—N1B—C1B—C12B88.6 (6)C12B—C13B—C14B—C15B179.4 (6)
C19B—N1B—C1B—C2B147.2 (5)C13A—C14A—C15A—C16A1.3 (9)
N1A—C1A—C2A—O1A66.7 (5)C13B—C14B—C15B—C16B1.0 (10)
C12—C1A—C2A—O1A56.2 (5)C14A—C15A—C16A—C17A1.1 (10)
N1A—C1A—C2A—C3A55.1 (5)C14B—C15B—C16B—C17B0.9 (10)
C12—C1A—C2A—C3A178.0 (4)C15A—C16A—C17A—C18A0.5 (11)
N1B—C1B—C2B—O1B67.8 (5)C15B—C16B—C17B—C18B0.1 (9)
C12B—C1B—C2B—O1B55.2 (5)C14A—C13A—C18A—C17A0.2 (9)
N1B—C1B—C2B—C3B57.5 (5)C12—C13A—C18A—C17A178.5 (6)
C12B—C1B—C2B—C3B179.6 (4)C16A—C17A—C18A—C13A0.1 (11)
O1A—C2A—C3A—C4A177.4 (4)C16B—C17B—C18B—C13B1.0 (8)
C1A—C2A—C3A—C4A58.7 (5)C14B—C13B—C18B—C17B1.0 (8)
O1B—C2B—C3B—C4B179.2 (4)C12B—C13B—C18B—C17B178.3 (5)
C1B—C2B—C3B—C4B59.4 (5)C1A—N1A—C19A—O2A0.5 (8)
C25A—N2A—C4A—C3A144.4 (5)C1A—N1A—C19A—C20A175.2 (4)
C25A—N2A—C4A—C5A90.8 (6)C1B—N1B—C19B—O2B0.6 (8)
C2A—C3A—C4A—N2A64.0 (5)C1B—N1B—C19B—C20B179.8 (4)
C2A—C3A—C4A—C5A171.2 (4)C24A—N3A—C20A—C21A1.5 (8)
C25B—N2B—C4B—C3B120.8 (5)C24A—N3A—C20A—C19A178.7 (5)
C25B—N2B—C4B—C5B114.5 (5)O2A—C19A—C20A—N3A174.7 (5)
C2B—C3B—C4B—N2B68.0 (5)N1A—C19A—C20A—N3A0.9 (7)
C2B—C3B—C4B—C5B168.3 (4)O2A—C19A—C20A—C21A8.1 (8)
N2A—C4A—C5A—C6A164.0 (4)N1A—C19A—C20A—C21A176.3 (5)
C3A—C4A—C5A—C6A72.8 (6)C24B—N3B—C20B—C21B1.2 (8)
N2B—C4B—C5B—C6B169.6 (4)C24B—N3B—C20B—C19B178.6 (5)
C3B—C4B—C5B—C6B66.9 (6)O2B—C19B—C20B—N3B178.2 (5)
C4A—C5A—C6A—C7A63.7 (7)N1B—C19B—C20B—N3B2.1 (7)
C4A—C5A—C6A—C11A116.2 (6)O2B—C19B—C20B—C21B1.5 (8)
C4B—C5B—C6B—C11B111.4 (6)N1B—C19B—C20B—C21B178.1 (5)
C4B—C5B—C6B—C7B63.3 (7)N3A—C20A—C21A—C22A0.2 (9)
C11A—C6A—C7A—C8A0.5 (9)C19A—C20A—C21A—C22A177.0 (6)
C5A—C6A—C7A—C8A179.6 (5)N3B—C20B—C21B—C22B2.4 (9)
C11B—C6B—C7B—C8B2.3 (8)C19B—C20B—C21B—C22B177.3 (5)
C5B—C6B—C7B—C8B177.3 (5)C20A—C21A—C22A—C23A0.7 (10)
C6A—C7A—C8A—C9A1.4 (10)C20B—C21B—C22B—C23B1.9 (9)
C6B—C7B—C8B—C9B0.5 (9)C21A—C22A—C23A—C24A0.4 (11)
C7A—C8A—C9A—C10A3.4 (11)C21B—C22B—C23B—C24B0.2 (9)
C7B—C8B—C9B—C10B1.1 (9)C20A—N3A—C24A—C23A2.7 (9)
C8A—C9A—C10A—C11A4.5 (12)C22A—C23A—C24A—N3A2.2 (11)
C8B—C9B—C10B—C11B3.6 (10)C20B—N3B—C24B—C23B0.6 (9)
C7A—C6A—C11A—C10A1.5 (9)C22B—C23B—C24B—N3B1.1 (10)
C5A—C6A—C11A—C10A178.6 (6)C4A—N2A—C25A—O3A3.5 (8)
C9A—C10A—C11A—C6A3.5 (11)C4A—N2A—C25A—O4A177.3 (4)
C9B—C10B—C11B—C6B5.6 (10)C26A—O4A—C25A—O3A4.3 (7)
C7B—C6B—C11B—C10B4.8 (9)C26A—O4A—C25A—N2A176.4 (4)
C5B—C6B—C11B—C10B179.6 (6)C26B—O4B—C25B—O3B11.5 (8)
N1A—C1A—C12—C13A174.2 (4)C26B—O4B—C25B—N2B169.9 (4)
C2A—C1A—C12—C13A65.0 (6)C4B—N2B—C25B—O3B5.5 (8)
N1B—C1B—C12B—C13B178.9 (4)C4B—N2B—C25B—O4B175.9 (4)
C2B—C1B—C12B—C13B59.0 (6)C25A—O4A—C26A—C28A56.5 (7)
C1A—C12—C13A—C18A87.8 (6)C25A—O4A—C26A—C27A67.7 (6)
C1A—C12—C13A—C14A93.6 (6)C25A—O4A—C26A—C29A172.7 (5)
C1B—C12B—C13B—C14B101.6 (6)C25B—O4B—C26B—C29B67.7 (6)
C1B—C12B—C13B—C18B79.1 (6)C25B—O4B—C26B—C27B59.8 (6)
C18A—C13A—C14A—C15A0.9 (9)C25B—O4B—C26B—C28B175.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O2B0.882.042.888 (5)162
O1A—H1AB···O3B0.841.892.707 (5)164
N2B—H2BA···O2Ai0.882.012.843 (5)159
O1B—H1BB···O3Ai0.841.882.711 (5)171
C23B—H23B···CgAii0.952.973.776 (4)144
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC29H35N3O4
Mr489.60
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)11.7573 (12), 15.9783 (18), 15.0881 (15)
β (°) 103.787 (9)
V3)2752.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.70 × 0.32 × 0.12
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.947, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
14395, 4903, 3396
Rint0.071
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.180, 1.19
No. of reflections4903
No. of parameters649
No. of restraints1
H-atom treatmentH-atom parameters constrained
(Δ/σ)max0.175
Δρmax, Δρmin (e Å3)0.30, 0.29
Absolute structureIndeterminate

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT (Bruker, 2001, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O2B0.882.042.888 (5)162
O1A—H1AB···O3B0.841.892.707 (5)164
N2B—H2BA···O2Ai0.882.012.843 (5)159
O1B—H1BB···O3Ai0.841.882.711 (5)171
C23B—H23B···CgAii0.952.973.776 (4)144
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1.
 

Acknowledgements

The authors thank the Natural Science Foundation of Fujian Province of China (No. U0650024), Xiamen Science Foundation (No.3502Z20055019) and NFFTBS (No. J0630429) for financial support. We also thank Mr Z.-B. Wei, Mr T.-B. Wen and Mr Y.-X. Gao for technical assistance.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationNishiyama, H., Sakaguchi, H., Nakamura, T., HoriHata, M., Kondo, M. & Itoh, K. (1989). Organometallics, 8, 846–848.  CSD CrossRef CAS Web of Science Google Scholar
First citationPavel, H., Heinrich, L. S. & Edward, W. S. (1993). J. Am. Chem. Soc. 116, 3500–3506.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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