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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages o3037-o3038
https://doi.org/10.1107/S1600536812040093

6-Hy­dr­oxy­imino-5α-cholestane

Shams Uzzaman,a* Hena Khanam,a Ashraf Mashrai,a Yahia Nasser Mabkhotb and Ahmad Husainc

aDepartment of Chemistry, Aligarh Muslim University, Aligarh 202 002, India, bDepartment of Chemistry, Faculty of Science, King Saud University, Riyadh 11451, Saudi Arabia, and cDepartment of Chemistry, University of Cape Town, Cape Town, South Africa
*Correspondence e-mail: shamsuzzaman9@gmail.com

(Received 7 August 2012; accepted 21 September 2012; online 29 September 2012)

The title compound, C27H47NO, is a steroid derivative composed of a saturated carbon fused-ring framework with an alkyl side chain. Ring bond lengths have normal values with an average of 1.533 (2) Å, while the cholestane side chain shows an average bond length of 1.533 (2) Å. The three cyclohexane rings adopt chair conformations or close to chair conformations while the cyclopentane ring is twisted. The cholesterol side-chain is fully extended with a gauche–trans conformation of the terminal methyl groups. There are eight chiral centres in the molecule; the absolute configuration of these sites was determined from the structure presented. There are two molecules in the asymmetric unit; in one, the alkyl chain is disordered over two sets of sites [occupancy ratios of 0.50:0.50 and 0.67:0.33].

Related literature

For background on steroidal hormone applications, see: Grover et al. (2007[Grover, V. K., Babu, R. & Bedi, S. P. S. (2007). Indian J. Anaesth. 51, 389-393.]). For background to this study and previous syntheses, see: Shoppee et al. (1955[Shoppee, C. W., Jones, D. N., Lewis, J. R. & Summers, G. H. R. (1955). J. Chem. Soc. pp. 2876-2887.]). For related structures, see: Ketuly et al. (2011[Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o773-o774.]); Park (2004[Park, Y. J. (2004). Bull. Korean Chem. Soc. 25, 751-753.]). For reference bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C27H47NO

  • Mr = 401.65

  • Monoclinic, P 21

  • a = 13.7535 (7) Å

  • b = 9.5266 (4) Å

  • c = 18.681 (1) Å

  • β = 102.829 (3)°

  • V = 2386.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.54 × 0.31 × 0.17 mm
Data collection

  • Bruker Kappa APEXII Duo diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.965, Tmax = 0.989

  • 51587 measured reflections

  • 7706 independent reflections

  • 6021 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.129

  • S = 1.12

  • 7706 reflections

  • 564 parameters

  • 59 restraints

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

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812040093/hg5240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040093/hg5240Isup2.hkl

checkCIF report


Comment top

Steroids are compounds of biological origin and play an important role in biological systems. The dramatic expansion of steroidal chemistry came with the discovery of steroidal hormones. The discovery of several steroids with their wide application in therapy has brought about an increasing interest (Grover et al., 2007). A series of crystal structures of hydroxyiminocholestane (Ketuly et al., 2011) and derivatives of cholesterol (Park, 2004) have been examined in order to obtain structural information relevant to the liquid crystalline phases and the possible modes of association of the cholesterol derivatives themselves.

In the view of the biological importance of cholesterol derivatives, we report here the crystal structure of the title compound (I). There are two molecules in the asymmetric unit (Fig. 1), while unit cell contains 4 molecules (Fig. 2). The ring bond lengths have normal values (Allen et al., 1987) with average C(sp3)—C(sp3) of 1.533 (2) Å, excluding the shorter C1—C62 bond of 1.496 (2) Å. The cholestane side-chain shows C(sp3)—C(sp3) bond lengths varying from C25—C26 [1.525 (2) Å] up to C20—C22 [1.539 (2) Å]. Each of the six-member rings adopts a chair conformation or close to a chair conformation, and the five-member ring has a twisted conformation. There are eight chiral centres in the molecule, the absolute configuration of these sites was determined from the structure presented, these sites exhibit the following chiralities: C2= S, C7 = R, C8 = S, C11 = R, C12 = R, C15 = S, C16 = S and C20 = R.

Related literature top

For background on steroidal hormone applications, see: Grover et al. (2007). For background to this study and previous syntheses, see: Shoppee et al. (1955). For related structures, see: Ketuly et al. (2011); Park (2004). For reference bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

5α-Cholest-6-one (1.0 g) was dissolved in ethanol (60 ml) and to this, hydroxylamine hydrochloride (1.0 g) and sodium acetate trihydrate (2.0 g) were added. The reaction mixture was refluxed for 4 h. Dilution with cold water gave crude oxime, which was filtered, washed with water and air dried. Recrystallization from ethanol gave crystals of product. m.p. 482 K (reported m.p. 477 K; Shoppee et al. 1955). 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.

Refinement top

All H atoms were positioned geometrically [C—H = 0.98–1.00 Å] and were refined using a riding model, with Uiso(H) = 1.2–1.5Ueq(C). H atoms attached to O atom were positioned with idealized geometry and were refined isotropically with Ueq(H) set to 1.5 times of Ueq(O) using a riding model with O—H = 0.87 Å. In the absence of significant anomalous scattering, Friedel pairs were merged and the absolute structure was assigned arbitrarily. Friedel pairs have been merged using MERG 3, which makes the Flack x parameter meaningless and therefore has been removed from the final cif file.

There are two molecules in the asymmetric unit and only alkyl chain (C23a—C25a) of one molecule is disordered. C23a and C25a are disordered over two positions with site occupancy factors of 50% while C24a is disordered over two positions with site occupancy factors of 33% and 67%.

Structure description top

Steroids are compounds of biological origin and play an important role in biological systems. The dramatic expansion of steroidal chemistry came with the discovery of steroidal hormones. The discovery of several steroids with their wide application in therapy has brought about an increasing interest (Grover et al., 2007). A series of crystal structures of hydroxyiminocholestane (Ketuly et al., 2011) and derivatives of cholesterol (Park, 2004) have been examined in order to obtain structural information relevant to the liquid crystalline phases and the possible modes of association of the cholesterol derivatives themselves.

In the view of the biological importance of cholesterol derivatives, we report here the crystal structure of the title compound (I). There are two molecules in the asymmetric unit (Fig. 1), while unit cell contains 4 molecules (Fig. 2). The ring bond lengths have normal values (Allen et al., 1987) with average C(sp3)—C(sp3) of 1.533 (2) Å, excluding the shorter C1—C62 bond of 1.496 (2) Å. The cholestane side-chain shows C(sp3)—C(sp3) bond lengths varying from C25—C26 [1.525 (2) Å] up to C20—C22 [1.539 (2) Å]. Each of the six-member rings adopts a chair conformation or close to a chair conformation, and the five-member ring has a twisted conformation. There are eight chiral centres in the molecule, the absolute configuration of these sites was determined from the structure presented, these sites exhibit the following chiralities: C2= S, C7 = R, C8 = S, C11 = R, C12 = R, C15 = S, C16 = S and C20 = R.

For background on steroidal hormone applications, see: Grover et al. (2007). For background to this study and previous syntheses, see: Shoppee et al. (1955). For related structures, see: Ketuly et al. (2011); Park (2004). For reference bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: APEX2 (Bruker, 2008); 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: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The unit cell diagram projected down the b axis.
6-Hydroxyimino-5α-cholestane top
Crystal data top
C27H47NOF(000) = 896
Mr = 401.65Dx = 1.118 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 10665 reflections
a = 13.7535 (7) Åθ = 1.7–30.6°
b = 9.5266 (4) ŵ = 0.07 mm−1
c = 18.681 (1) ÅT = 100 K
β = 102.829 (3)°Plate, colourless
V = 2386.6 (2) Å30.54 × 0.31 × 0.17 mm
Z = 4
Data collection top
Bruker Kappa APEXII Duo
diffractometer		7706 independent reflections
Radiation source: fine-focus sealed tube6021 reflections with I > 2σ(I)
Triumph monochromatorRint = 0.052
Detector resolution: 0 pixels mm-1θmax = 30.6°, θmin = 1.7°
ω and φ scansh = −18→19
Absorption correction: multi-scan
(Blessing, 1995)		k = −13→13
Tmin = 0.965, Tmax = 0.989l = −26→26
51587 measured reflections
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.5458P]
where P = (Fo2 + 2Fc2)/3
7706 reflections(Δ/σ)max = 0.005
564 parametersΔρmax = 0.48 e Å−3
59 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C27H47NOV = 2386.6 (2) Å3
Mr = 401.65Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.7535 (7) ŵ = 0.07 mm−1
b = 9.5266 (4) ÅT = 100 K
c = 18.681 (1) Å0.54 × 0.31 × 0.17 mm
β = 102.829 (3)°
Data collection top
Bruker Kappa APEXII Duo
diffractometer		7706 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		6021 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.989Rint = 0.052
51587 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04959 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.48 e Å−3
7706 reflectionsΔρmin = −0.32 e Å−3
564 parameters
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*/UeqOcc. (<1)
O1A0.61310 (13)0.1041 (2)0.17724 (10)0.0271 (4)
H1A0.585 (2)0.091 (4)0.1311 (19)0.041*
C1A0.77678 (17)0.0812 (2)0.22893 (13)0.0190 (4)
N1A0.71254 (15)0.0947 (2)0.16853 (11)0.0223 (4)
C2A0.88428 (18)0.0668 (3)0.22606 (13)0.0217 (5)
H2A0.9058−0.02690.24810.026*
C3A0.9035 (2)0.0630 (3)0.14838 (14)0.0307 (6)
H3A10.8627−0.01200.11960.037*
H3A20.88360.15370.12360.037*
C4A1.0132 (2)0.0357 (4)0.15124 (16)0.0403 (8)
H4A11.0317−0.05840.17230.048*
H4A21.02500.03730.10080.048*
C5A1.0775 (2)0.1455 (4)0.19742 (17)0.0402 (8)
H5A11.06330.23840.17360.048*
H5A21.14860.12350.20020.048*
C6A1.05897 (18)0.1526 (3)0.27529 (16)0.0296 (6)
H6A11.09960.22960.30230.036*
H6A21.08180.06370.30110.036*
C7A0.94860 (17)0.1770 (3)0.27754 (15)0.0216 (5)
C8A0.93347 (16)0.1497 (2)0.35607 (13)0.0183 (4)
H8A0.95220.04930.36720.022*
C9A1.00016 (18)0.2365 (3)0.41720 (15)0.0260 (5)
H9A11.07070.22270.41490.031*
H9A20.98420.33720.40840.031*
C10A0.98758 (18)0.1972 (3)0.49393 (15)0.0251 (5)
H10A1.02900.26070.53030.030*
H10B1.01210.10030.50530.030*
C11A0.87903 (17)0.2066 (2)0.50136 (13)0.0205 (5)
C12A0.85108 (17)0.1293 (3)0.56717 (13)0.0218 (5)
H12A0.88230.03410.56970.026*
C13A0.73665 (18)0.1076 (3)0.54132 (13)0.0255 (5)
H13A0.71700.01570.55840.031*
H13B0.70030.18250.56120.031*
C14A0.71249 (17)0.1130 (3)0.45644 (13)0.0227 (5)
H14A0.67560.02820.43510.027*
H14B0.67260.19730.43800.027*
C15A0.81518 (16)0.1194 (2)0.43825 (13)0.0188 (4)
H15A0.84220.02170.44510.023*
C16A0.82378 (16)0.1631 (2)0.36144 (13)0.0185 (4)
H16A0.80280.26340.35340.022*
C17A0.75460 (17)0.0716 (3)0.30388 (13)0.0213 (5)
H17A0.7611−0.02750.32030.026*
H17B0.68470.10070.30080.026*
C18A0.9167 (2)0.3268 (3)0.25160 (17)0.0309 (6)
H18A0.95260.39480.28730.046*
H18B0.84480.33740.24730.046*
H18C0.93260.34360.20370.046*
C19A0.84505 (19)0.3604 (3)0.49939 (15)0.0243 (5)
H19A0.84920.40240.45230.036*
H19B0.88830.41230.53940.036*
H19C0.77600.36460.50520.036*
C20A0.8800 (2)0.1919 (3)0.64513 (14)0.0262 (5)
H20A0.84430.28330.64530.031*
C21A0.9927 (2)0.2192 (3)0.66857 (16)0.0366 (7)
H21A1.01020.24330.72090.055*
H21B1.01070.29710.63980.055*
H21C1.02900.13460.66000.055*
C22A0.8456 (2)0.0920 (3)0.69885 (14)0.0283 (6)
H22A0.89510.01510.71040.034*
H22B0.78180.04930.67300.034*
C23A0.8299 (5)0.1538 (7)0.7740 (3)0.0367 (14)0.50
H23A0.88990.21110.79400.044*0.50
H23B0.77360.22060.76090.044*0.50
C24A0.8103 (6)0.0677 (10)0.8393 (4)0.0321 (18)0.33
H24A0.7725−0.01750.81950.039*0.33
H24B0.76690.12400.86400.039*0.33
C25A0.9059 (3)0.0193 (5)0.9001 (2)0.0192 (9)0.50
H25A0.9619−0.02050.88030.023*0.50
C23C0.8831 (5)0.1306 (6)0.7778 (3)0.0309 (12)0.50
H23C0.85700.22380.78750.037*0.50
H23D0.95690.13540.78950.037*0.50
C24C0.8488 (3)0.0208 (4)0.82512 (18)0.0195 (7)0.67
H24C0.7828−0.01240.79780.023*0.67
H24D0.8951−0.05970.82820.023*0.67
C25C0.8391 (4)0.0519 (6)0.9022 (3)0.0339 (12)0.50
H25C0.77270.09400.90290.041*0.50
C26A0.9295 (3)0.1526 (3)0.94258 (16)0.0392 (7)
H26D0.98980.14110.98110.059*0.50
H26E0.94170.22690.91050.059*0.50
H26F0.87590.17820.96450.059*0.50
H26G0.92640.24140.91760.059*0.50
H26H0.92610.16720.99250.059*0.50
H26I0.99380.10940.94170.059*0.50
C27A0.8563 (3)−0.0864 (3)0.94673 (17)0.0457 (8)
H27D0.9057−0.12840.98570.069*0.50
H27E0.8078−0.03870.96800.069*0.50
H27F0.8231−0.16050.91510.069*0.50
H27G0.8061−0.15450.92640.069*0.50
H27H0.9211−0.12460.94570.069*0.50
H27I0.8534−0.06680.99640.069*0.50
O1B0.33906 (12)0.5733 (2)−0.01531 (10)0.0226 (4)
H1B0.306 (2)0.588 (4)−0.0599 (18)0.034*
C1B0.49582 (17)0.4940 (2)0.02841 (12)0.0170 (4)
N1B0.43489 (14)0.5418 (2)−0.02822 (10)0.0178 (4)
C2B0.59958 (17)0.4588 (2)0.02224 (12)0.0166 (4)
H2B0.61280.36170.04230.020*
C3B0.61520 (18)0.4535 (3)−0.05631 (12)0.0203 (5)
H3B10.56580.3891−0.08610.024*
H3B20.60480.5481−0.07860.024*
C4B0.72015 (18)0.4031 (3)−0.05655 (13)0.0222 (5)
H4B10.73040.4051−0.10740.027*
H4B20.72830.3049−0.03880.027*
C5B0.79807 (19)0.4957 (3)−0.00758 (14)0.0233 (5)
H5B10.79530.5911−0.02890.028*
H5B20.86530.4569−0.00580.028*
C6B0.78092 (17)0.5050 (3)0.07050 (13)0.0216 (5)
H6B10.83080.56990.09950.026*
H6B20.79200.41120.09370.026*
C7B0.67551 (16)0.5563 (2)0.07400 (12)0.0163 (4)
C8B0.65899 (16)0.5382 (2)0.15342 (12)0.0159 (4)
H8B0.67370.43760.16700.019*
C9B0.73071 (17)0.6262 (3)0.21092 (13)0.0198 (5)
H9B10.72200.72650.19710.024*
H9B20.80010.59970.21020.024*
C10B0.71515 (17)0.6082 (3)0.28966 (12)0.0197 (5)
H10C0.73400.51150.30670.024*
H10D0.75950.67400.32280.024*
C11B0.60703 (16)0.6356 (2)0.29422 (12)0.0156 (4)
C12B0.57603 (17)0.5883 (2)0.36572 (12)0.0182 (4)
H12B0.60610.49370.37930.022*
C13B0.46118 (18)0.5684 (3)0.34010 (12)0.0200 (5)
H13C0.43930.48560.36440.024*
H13D0.42580.65220.35260.024*
C14B0.43838 (18)0.5467 (3)0.25580 (12)0.0199 (5)
H14C0.40000.45930.24170.024*
H14D0.40010.62690.23000.024*
C15B0.54085 (16)0.5372 (2)0.23794 (11)0.0156 (4)
H15B0.56550.43960.25040.019*
C16B0.54998 (16)0.5646 (2)0.15896 (11)0.0149 (4)
H16B0.53410.66570.14750.018*
C17B0.47601 (17)0.4750 (3)0.10383 (12)0.0188 (5)
H17C0.48370.37490.11820.023*
H17D0.40690.50400.10380.023*
C18B0.66091 (19)0.7094 (2)0.04869 (14)0.0215 (5)
H18D0.71330.76760.07860.032*
H18E0.59550.74250.05430.032*
H18F0.66460.7160−0.00300.032*
C19B0.57851 (18)0.7902 (2)0.27894 (13)0.0191 (4)
H19D0.61640.84860.31860.029*
H19E0.50700.80210.27620.029*
H19F0.59390.81850.23220.029*
C20B0.60358 (18)0.6827 (2)0.43447 (12)0.0198 (5)
H20B0.56770.77400.42260.024*
C21B0.71555 (19)0.7145 (3)0.45636 (14)0.0264 (5)
H21D0.73070.76310.50380.040*
H21E0.73440.77430.41900.040*
H21F0.75320.62640.46030.040*
C22B0.5687 (2)0.6171 (3)0.49985 (13)0.0235 (5)
H22C0.50190.57490.48200.028*
H22D0.61530.54100.52110.028*
C23B0.5635 (2)0.7249 (3)0.55994 (13)0.0257 (5)
H23E0.62700.77780.57100.031*
H23F0.50970.79250.53990.031*
C24B0.54498 (18)0.6672 (3)0.63243 (13)0.0223 (5)
H24E0.50530.73720.65290.027*
H24F0.50390.58120.62150.027*
C25B0.63789 (17)0.6318 (3)0.69153 (12)0.0195 (5)
H25B0.68520.71260.69510.023*
C26B0.61099 (19)0.6148 (3)0.76606 (13)0.0242 (5)
H26A0.57600.69900.77700.036*
H26B0.67200.60170.80410.036*
H26C0.56770.53280.76490.036*
C27B0.69108 (19)0.5011 (3)0.67274 (15)0.0273 (5)
H27A0.74620.47750.71400.041*
H27B0.71730.51920.62890.041*
H27C0.64390.42260.66320.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0173 (8)0.0416 (11)0.0223 (9)−0.0053 (8)0.0042 (7)−0.0046 (8)
C1A0.0198 (11)0.0177 (10)0.0207 (11)−0.0026 (9)0.0069 (9)−0.0005 (8)
N1A0.0184 (9)0.0247 (10)0.0253 (10)−0.0018 (8)0.0079 (8)−0.0001 (8)
C2A0.0210 (11)0.0218 (11)0.0240 (12)0.0049 (9)0.0087 (9)0.0053 (9)
C3A0.0287 (14)0.0415 (16)0.0249 (13)0.0109 (12)0.0124 (10)0.0111 (11)
C4A0.0325 (15)0.063 (2)0.0299 (14)0.0213 (15)0.0167 (12)0.0167 (14)
C5A0.0210 (13)0.061 (2)0.0428 (17)0.0150 (14)0.0167 (12)0.0300 (15)
C6A0.0132 (11)0.0363 (15)0.0406 (15)0.0057 (10)0.0085 (10)0.0173 (12)
C7A0.0127 (11)0.0193 (11)0.0330 (13)0.0022 (9)0.0050 (9)0.0083 (9)
C8A0.0123 (10)0.0137 (10)0.0285 (12)0.0013 (8)0.0038 (9)0.0010 (9)
C9A0.0122 (11)0.0239 (12)0.0409 (15)−0.0034 (9)0.0040 (10)−0.0065 (11)
C10A0.0131 (11)0.0268 (12)0.0324 (13)0.0005 (9)−0.0016 (9)−0.0082 (10)
C11A0.0146 (11)0.0177 (10)0.0266 (12)0.0021 (9)−0.0008 (9)−0.0087 (9)
C12A0.0191 (11)0.0169 (10)0.0272 (12)0.0041 (9)0.0004 (9)−0.0058 (9)
C13A0.0210 (12)0.0317 (13)0.0233 (12)0.0020 (10)0.0034 (9)−0.0073 (10)
C14A0.0171 (11)0.0267 (12)0.0233 (12)−0.0015 (9)0.0021 (9)−0.0069 (10)
C15A0.0131 (10)0.0177 (10)0.0248 (11)−0.0001 (8)0.0022 (8)−0.0062 (9)
C16A0.0121 (10)0.0161 (10)0.0263 (12)−0.0014 (8)0.0021 (8)−0.0034 (8)
C17A0.0156 (10)0.0253 (12)0.0233 (11)−0.0061 (9)0.0049 (8)−0.0036 (9)
C18A0.0222 (13)0.0222 (12)0.0464 (17)0.0007 (10)0.0033 (11)0.0111 (11)
C19A0.0215 (12)0.0184 (11)0.0308 (14)0.0040 (9)0.0009 (10)−0.0064 (9)
C20A0.0322 (14)0.0173 (11)0.0240 (12)0.0035 (10)−0.0048 (10)−0.0034 (9)
C21A0.0397 (16)0.0263 (13)0.0333 (15)−0.0116 (12)−0.0142 (12)0.0052 (11)
C22A0.0265 (13)0.0225 (12)0.0305 (14)0.0031 (10)−0.0054 (10)0.0008 (10)
C23A0.042 (2)0.036 (2)0.030 (2)−0.0142 (17)0.0005 (17)0.0047 (16)
C24A0.036 (3)0.031 (2)0.027 (2)−0.0029 (19)0.0029 (18)0.0015 (18)
C25A0.0153 (16)0.0239 (16)0.0203 (16)0.0007 (14)0.0080 (13)−0.0069 (14)
C23C0.041 (2)0.0281 (19)0.0241 (18)−0.0026 (17)0.0079 (16)0.0001 (15)
C24C0.0178 (13)0.0242 (14)0.0176 (13)0.0039 (12)0.0060 (11)0.0027 (11)
C25C0.036 (2)0.0318 (19)0.0330 (19)0.0023 (16)0.0065 (16)0.0014 (16)
C26A0.0529 (15)0.0336 (13)0.0274 (12)0.0046 (12)0.0009 (11)−0.0019 (10)
C27A0.0711 (17)0.0354 (13)0.0297 (13)−0.0002 (13)0.0092 (12)0.0034 (11)
O1B0.0138 (8)0.0315 (9)0.0222 (8)0.0029 (7)0.0037 (6)−0.0031 (7)
C1B0.0194 (11)0.0167 (10)0.0158 (10)−0.0029 (8)0.0054 (8)−0.0015 (8)
N1B0.0136 (9)0.0205 (9)0.0198 (9)0.0000 (7)0.0049 (7)−0.0024 (7)
C2B0.0200 (11)0.0151 (10)0.0155 (10)0.0004 (8)0.0055 (8)0.0005 (8)
C3B0.0216 (12)0.0244 (11)0.0163 (10)0.0010 (9)0.0071 (9)−0.0002 (9)
C4B0.0253 (12)0.0220 (11)0.0216 (12)0.0050 (10)0.0103 (10)0.0012 (9)
C5B0.0206 (12)0.0250 (12)0.0267 (12)0.0034 (10)0.0107 (10)0.0013 (9)
C6B0.0172 (11)0.0268 (12)0.0222 (12)0.0026 (9)0.0078 (9)0.0017 (9)
C7B0.0148 (10)0.0166 (10)0.0177 (10)−0.0002 (8)0.0039 (8)0.0015 (8)
C8B0.0160 (10)0.0167 (10)0.0152 (10)0.0001 (8)0.0038 (8)0.0007 (8)
C9B0.0151 (10)0.0218 (11)0.0224 (11)−0.0009 (9)0.0042 (8)−0.0029 (9)
C10B0.0162 (10)0.0237 (11)0.0180 (11)0.0041 (9)0.0014 (8)−0.0025 (9)
C11B0.0161 (10)0.0140 (10)0.0161 (10)0.0013 (8)0.0020 (8)−0.0011 (8)
C12B0.0235 (11)0.0143 (10)0.0167 (10)0.0030 (9)0.0043 (8)−0.0003 (8)
C13B0.0258 (12)0.0203 (11)0.0155 (10)−0.0027 (9)0.0078 (9)−0.0011 (8)
C14B0.0221 (11)0.0230 (11)0.0160 (10)−0.0067 (9)0.0073 (8)−0.0017 (8)
C15B0.0194 (11)0.0138 (9)0.0136 (10)−0.0024 (8)0.0034 (8)−0.0009 (7)
C16B0.0149 (10)0.0165 (10)0.0138 (9)−0.0009 (8)0.0039 (7)−0.0002 (7)
C17B0.0182 (11)0.0220 (11)0.0172 (10)−0.0029 (9)0.0060 (9)−0.0013 (8)
C18B0.0257 (12)0.0155 (10)0.0250 (12)−0.0008 (9)0.0091 (10)0.0029 (9)
C19B0.0206 (11)0.0131 (10)0.0231 (11)0.0001 (8)0.0041 (9)0.0012 (8)
C20B0.0236 (12)0.0168 (10)0.0183 (11)0.0028 (9)0.0028 (9)−0.0012 (8)
C21B0.0278 (13)0.0280 (12)0.0216 (12)0.0054 (11)0.0018 (10)−0.0073 (10)
C22B0.0344 (14)0.0190 (11)0.0166 (11)0.0018 (10)0.0045 (9)−0.0017 (9)
C23B0.0396 (15)0.0200 (11)0.0170 (11)0.0050 (11)0.0052 (10)−0.0013 (9)
C24B0.0241 (12)0.0232 (11)0.0189 (11)0.0023 (10)0.0032 (9)−0.0018 (9)
C25B0.0167 (10)0.0220 (11)0.0197 (11)−0.0029 (9)0.0036 (8)−0.0008 (9)
C26B0.0266 (13)0.0277 (12)0.0186 (11)−0.0024 (10)0.0053 (9)0.0004 (10)
C27B0.0206 (12)0.0335 (14)0.0264 (13)0.0058 (11)0.0020 (10)−0.0035 (11)
Geometric parameters (Å, º) top
O1A—N1A1.416 (3)C26A—H26H0.9543
O1A—H1A0.87 (3)C26A—H26I0.9786
C1A—N1A1.276 (3)C27A—H27D0.9659
C1A—C17A1.501 (3)C27A—H27E0.9622
C1A—C2A1.498 (3)C27A—H27F0.9675
C2A—C3A1.532 (3)C27A—H27G0.9617
C2A—C7A1.559 (4)C27A—H27H0.9675
C2A—H2A1.0000C27A—H27I0.9558
C3A—C4A1.520 (4)O1B—N1B1.423 (2)
C3A—H3A10.9900O1B—H1B0.87 (3)
C3A—H3A20.9900C1B—N1B1.279 (3)
C4A—C5A1.511 (5)C1B—C2B1.495 (3)
C4A—H4A10.9900C1B—C17B1.504 (3)
C4A—H4A20.9900C2B—C3B1.530 (3)
C5A—C6A1.533 (4)C2B—C7B1.562 (3)
C5A—H5A10.9900C2B—H2B1.0000
C5A—H5A20.9900C3B—C4B1.522 (3)
C6A—C7A1.545 (3)C3B—H3B10.9900
C6A—H6A10.9900C3B—H3B20.9900
C6A—H6A20.9900C4B—C5B1.526 (4)
C7A—C18A1.539 (3)C4B—H4B10.9900
C7A—C8A1.549 (3)C4B—H4B20.9900
C8A—C16A1.539 (3)C5B—C6B1.531 (3)
C8A—C9A1.538 (3)C5B—H5B10.9900
C8A—H8A1.0000C5B—H5B20.9900
C9A—C10A1.528 (4)C6B—C7B1.545 (3)
C9A—H9A10.9900C6B—H6B10.9900
C9A—H9A20.9900C6B—H6B20.9900
C10A—C11A1.532 (3)C7B—C18B1.533 (3)
C10A—H10A0.9900C7B—C8B1.559 (3)
C10A—H10B0.9900C8B—C9B1.536 (3)
C11A—C19A1.536 (3)C8B—C16B1.546 (3)
C11A—C15A1.546 (3)C8B—H8B1.0000
C11A—C12A1.553 (4)C9B—C10B1.542 (3)
C12A—C20A1.542 (3)C9B—H9B10.9900
C12A—C13A1.554 (3)C9B—H9B20.9900
C12A—H12A1.0000C10B—C11B1.531 (3)
C13A—C14A1.547 (3)C10B—H10C0.9900
C13A—H13A0.9900C10B—H10D0.9900
C13A—H13B0.9900C11B—C19B1.534 (3)
C14A—C15A1.526 (3)C11B—C15B1.545 (3)
C14A—H14A0.9900C11B—C12B1.556 (3)
C14A—H14B0.9900C12B—C20B1.545 (3)
C15A—C16A1.523 (3)C12B—C13B1.557 (3)
C15A—H15A1.0000C12B—H12B1.0000
C16A—C17A1.539 (3)C13B—C14B1.550 (3)
C16A—H16A1.0000C13B—H13C0.9900
C17A—H17A0.9900C13B—H13D0.9900
C17A—H17B0.9900C14B—C15B1.521 (3)
C18A—H18A0.9800C14B—H14C0.9900
C18A—H18B0.9800C14B—H14D0.9900
C18A—H18C0.9800C15B—C16B1.531 (3)
C19A—H19A0.9800C15B—H15B1.0000
C19A—H19B0.9800C16B—C17B1.536 (3)
C19A—H19C0.9800C16B—H16B1.0000
C20A—C21A1.536 (4)C17B—H17C0.9900
C20A—C22A1.532 (4)C17B—H17D0.9900
C20A—H20A1.0000C18B—H18D0.9800
C21A—H21A0.9800C18B—H18E0.9800
C21A—H21B0.9800C18B—H18F0.9800
C21A—H21C0.9800C19B—H19D0.9800
C22A—C23C1.496 (5)C19B—H19E0.9800
C22A—C23A1.581 (6)C19B—H19F0.9800
C22A—H22A0.9900C20B—C21B1.533 (4)
C22A—H22B0.9900C20B—C22B1.541 (3)
C23A—C24A1.542 (7)C20B—H20B1.0000
C23A—H23A0.9900C21B—H21D0.9800
C23A—H23B0.9900C21B—H21E0.9800
C24A—C25A1.603 (7)C21B—H21F0.9800
C24A—H24A0.9900C22B—C23B1.535 (3)
C24A—H24B0.9900C22B—H22C0.9900
C25A—C26A1.494 (5)C22B—H22D0.9900
C25A—C27A1.582 (5)C23B—C24B1.534 (3)
C25A—H25A1.0000C23B—H23E0.9900
C23C—C24C1.511 (6)C23B—H23F0.9900
C23C—H23C0.9900C24B—C25B1.529 (3)
C23C—H23D0.9900C24B—H24E0.9900
C24C—C25C1.505 (6)C24B—H24F0.9900
C24C—H24C0.9900C25B—C27B1.524 (4)
C24C—H24D0.9900C25B—C26B1.527 (3)
C25C—C27A1.548 (6)C25B—H25B1.0000
C25C—C26A1.618 (6)C26B—H26A0.9800
C25C—H25C1.0000C26B—H26B0.9800
C26A—H26D0.9758C26B—H26C0.9800
C26A—H26E0.9658C27B—H27A0.9800
C26A—H26F0.9514C27B—H27B0.9800
C26A—H26G0.9625C27B—H27C0.9800
N1A—O1A—H1A96 (2)C25C—C26A—H26I110.3
N1A—C1A—C17A126.0 (2)H26D—C26A—H26I48.9
N1A—C1A—C2A118.2 (2)H26E—C26A—H26I90.9
C17A—C1A—C2A115.76 (19)H26F—C26A—H26I154.8
C1A—N1A—O1A113.69 (19)H26G—C26A—H26I107.7
C1A—C2A—C3A114.6 (2)H26H—C26A—H26I108.6
C1A—C2A—C7A110.2 (2)C25C—C27A—H27D139.1
C3A—C2A—C7A114.0 (2)C25A—C27A—H27D111.2
C1A—C2A—H2A105.7C25C—C27A—H27E77.5
C3A—C2A—H2A105.7C25A—C27A—H27E110.5
C7A—C2A—H2A105.7H27D—C27A—H27E108.7
C4A—C3A—C2A110.5 (2)C25C—C27A—H27F107.4
C4A—C3A—H3A1109.6C25A—C27A—H27F109.3
C2A—C3A—H3A1109.6H27D—C27A—H27F108.4
C4A—C3A—H3A2109.6H27E—C27A—H27F108.7
C2A—C3A—H3A2109.6C25C—C27A—H27G110.6
H3A1—C3A—H3A2108.1C25A—C27A—H27G124.9
C5A—C4A—C3A110.6 (3)H27D—C27A—H27G109.9
C5A—C4A—H4A1109.5H27E—C27A—H27G88.8
C3A—C4A—H4A1109.5C25C—C27A—H27H109.9
C5A—C4A—H4A2109.5C25A—C27A—H27H73.5
C3A—C4A—H4A2109.5H27D—C27A—H27H50.3
H4A1—C4A—H4A2108.1H27E—C27A—H27H155.8
C4A—C5A—C6A111.9 (2)H27F—C27A—H27H91.4
C4A—C5A—H5A1109.2H27G—C27A—H27H108.8
C6A—C5A—H5A1109.2C25C—C27A—H27I108.7
C4A—C5A—H5A2109.2C25A—C27A—H27I121.7
C6A—C5A—H5A2109.2H27D—C27A—H27I61.5
H5A1—C5A—H5A2107.9H27E—C27A—H27I47.6
C5A—C6A—C7A113.8 (2)H27F—C27A—H27I128.3
C5A—C6A—H6A1108.8H27G—C27A—H27I109.5
C7A—C6A—H6A1108.8H27H—C27A—H27I109.2
C5A—C6A—H6A2108.8N1B—O1B—H1B100 (2)
C7A—C6A—H6A2108.8N1B—C1B—C2B118.5 (2)
H6A1—C6A—H6A2107.7N1B—C1B—C17B126.6 (2)
C18A—C7A—C6A110.1 (2)C2B—C1B—C17B114.83 (19)
C18A—C7A—C8A111.4 (2)C1B—N1B—O1B113.34 (19)
C6A—C7A—C8A109.87 (19)C1B—C2B—C3B114.90 (18)
C18A—C7A—C2A110.3 (2)C1B—C2B—C7B109.72 (18)
C6A—C7A—C2A108.0 (2)C3B—C2B—C7B113.36 (19)
C8A—C7A—C2A107.09 (18)C1B—C2B—H2B106.0
C16A—C8A—C9A109.79 (19)C3B—C2B—H2B106.0
C16A—C8A—C7A112.80 (18)C7B—C2B—H2B106.0
C9A—C8A—C7A115.4 (2)C4B—C3B—C2B110.39 (19)
C16A—C8A—H8A106.0C4B—C3B—H3B1109.6
C9A—C8A—H8A106.0C2B—C3B—H3B1109.6
C7A—C8A—H8A106.0C4B—C3B—H3B2109.6
C10A—C9A—C8A113.1 (2)C2B—C3B—H3B2109.6
C10A—C9A—H9A1109.0H3B1—C3B—H3B2108.1
C8A—C9A—H9A1109.0C3B—C4B—C5B110.9 (2)
C10A—C9A—H9A2109.0C3B—C4B—H4B1109.5
C8A—C9A—H9A2109.0C5B—C4B—H4B1109.5
H9A1—C9A—H9A2107.8C3B—C4B—H4B2109.5
C9A—C10A—C11A112.7 (2)C5B—C4B—H4B2109.5
C9A—C10A—H10A109.0H4B1—C4B—H4B2108.1
C11A—C10A—H10A109.0C4B—C5B—C6B111.6 (2)
C9A—C10A—H10B109.0C4B—C5B—H5B1109.3
C11A—C10A—H10B109.0C6B—C5B—H5B1109.3
H10A—C10A—H10B107.8C4B—C5B—H5B2109.3
C10A—C11A—C19A110.5 (2)C6B—C5B—H5B2109.3
C10A—C11A—C15A107.43 (19)H5B1—C5B—H5B2108.0
C19A—C11A—C15A112.08 (19)C5B—C6B—C7B113.79 (19)
C10A—C11A—C12A117.5 (2)C5B—C6B—H6B1108.8
C19A—C11A—C12A110.1 (2)C7B—C6B—H6B1108.8
C15A—C11A—C12A98.66 (19)C5B—C6B—H6B2108.8
C20A—C12A—C11A120.5 (2)C7B—C6B—H6B2108.8
C20A—C12A—C13A112.1 (2)H6B1—C6B—H6B2107.7
C11A—C12A—C13A103.23 (19)C18B—C7B—C6B110.33 (19)
C20A—C12A—H12A106.7C18B—C7B—C8B111.22 (19)
C11A—C12A—H12A106.7C6B—C7B—C8B109.98 (18)
C13A—C12A—H12A106.7C18B—C7B—C2B110.54 (18)
C14A—C13A—C12A106.6 (2)C6B—C7B—C2B106.90 (19)
C14A—C13A—H13A110.4C8B—C7B—C2B107.74 (17)
C12A—C13A—H13A110.4C9B—C8B—C16B110.23 (18)
C14A—C13A—H13B110.4C9B—C8B—C7B113.48 (18)
C12A—C13A—H13B110.4C16B—C8B—C7B113.20 (17)
H13A—C13A—H13B108.6C9B—C8B—H8B106.5
C15A—C14A—C13A103.35 (18)C16B—C8B—H8B106.5
C15A—C14A—H14A111.1C7B—C8B—H8B106.5
C13A—C14A—H14A111.1C8B—C9B—C10B113.74 (19)
C15A—C14A—H14B111.1C8B—C9B—H9B1108.8
C13A—C14A—H14B111.1C10B—C9B—H9B1108.8
H14A—C14A—H14B109.1C8B—C9B—H9B2108.8
C16A—C15A—C14A119.35 (19)C10B—C9B—H9B2108.8
C16A—C15A—C11A114.9 (2)H9B1—C9B—H9B2107.7
C14A—C15A—C11A104.40 (18)C11B—C10B—C9B112.10 (18)
C16A—C15A—H15A105.7C11B—C10B—H10C109.2
C14A—C15A—H15A105.7C9B—C10B—H10C109.2
C11A—C15A—H15A105.7C11B—C10B—H10D109.2
C15A—C16A—C8A108.72 (18)C9B—C10B—H10D109.2
C15A—C16A—C17A109.77 (19)H10C—C10B—H10D107.9
C8A—C16A—C17A111.73 (19)C10B—C11B—C19B111.40 (19)
C15A—C16A—H16A108.9C10B—C11B—C15B106.94 (18)
C8A—C16A—H16A108.9C19B—C11B—C15B111.59 (18)
C17A—C16A—H16A108.9C10B—C11B—C12B116.93 (18)
C1A—C17A—C16A113.28 (19)C19B—C11B—C12B109.29 (19)
C1A—C17A—H17A108.9C15B—C11B—C12B100.14 (17)
C16A—C17A—H17A108.9C20B—C12B—C11B118.77 (19)
C1A—C17A—H17B108.9C20B—C12B—C13B111.80 (18)
C16A—C17A—H17B108.9C11B—C12B—C13B102.94 (17)
H17A—C17A—H17B107.7C20B—C12B—H12B107.6
C7A—C18A—H18A109.5C11B—C12B—H12B107.6
C7A—C18A—H18B109.5C13B—C12B—H12B107.6
H18A—C18A—H18B109.5C14B—C13B—C12B106.93 (18)
C7A—C18A—H18C109.5C14B—C13B—H13C110.3
H18A—C18A—H18C109.5C12B—C13B—H13C110.3
H18B—C18A—H18C109.5C14B—C13B—H13D110.3
C11A—C19A—H19A109.5C12B—C13B—H13D110.3
C11A—C19A—H19B109.5H13C—C13B—H13D108.6
H19A—C19A—H19B109.5C15B—C14B—C13B104.03 (18)
C11A—C19A—H19C109.5C15B—C14B—H14C111.0
H19A—C19A—H19C109.5C13B—C14B—H14C111.0
H19B—C19A—H19C109.5C15B—C14B—H14D111.0
C21A—C20A—C22A110.9 (2)C13B—C14B—H14D111.0
C21A—C20A—C12A111.5 (2)H14C—C14B—H14D109.0
C22A—C20A—C12A109.1 (2)C14B—C15B—C16B118.65 (18)
C21A—C20A—H20A108.4C14B—C15B—C11B104.42 (17)
C22A—C20A—H20A108.4C16B—C15B—C11B112.97 (18)
C12A—C20A—H20A108.4C14B—C15B—H15B106.7
C20A—C21A—H21A109.5C16B—C15B—H15B106.7
C20A—C21A—H21B109.5C11B—C15B—H15B106.7
H21A—C21A—H21B109.5C15B—C16B—C17B111.56 (18)
C20A—C21A—H21C109.5C15B—C16B—C8B108.96 (17)
H21A—C21A—H21C109.5C17B—C16B—C8B111.85 (18)
H21B—C21A—H21C109.5C15B—C16B—H16B108.1
C23C—C22A—C20A113.8 (3)C17B—C16B—H16B108.1
C20A—C22A—C23A118.2 (3)C8B—C16B—H16B108.1
C23C—C22A—H22A84.1C1B—C17B—C16B109.29 (18)
C20A—C22A—H22A107.8C1B—C17B—H17C109.8
C23A—C22A—H22A107.8C16B—C17B—H17C109.8
C23C—C22A—H22B131.0C1B—C17B—H17D109.8
C20A—C22A—H22B107.8C16B—C17B—H17D109.8
C23A—C22A—H22B107.8H17C—C17B—H17D108.3
H22A—C22A—H22B107.1C7B—C18B—H18D109.5
C24A—C23A—C22A125.9 (6)C7B—C18B—H18E109.5
C24A—C23A—H23A105.8H18D—C18B—H18E109.5
C22A—C23A—H23A105.8C7B—C18B—H18F109.5
C24A—C23A—H23B105.8H18D—C18B—H18F109.5
C22A—C23A—H23B105.8H18E—C18B—H18F109.5
H23A—C23A—H23B106.2C11B—C19B—H19D109.5
C23A—C24A—C25A116.9 (6)C11B—C19B—H19E109.5
C23A—C24A—H24A108.1H19D—C19B—H19E109.5
C25A—C24A—H24A108.1C11B—C19B—H19F109.5
C23A—C24A—H24B108.1H19D—C19B—H19F109.5
C25A—C24A—H24B108.1H19E—C19B—H19F109.5
H24A—C24A—H24B107.3C21B—C20B—C22B109.9 (2)
C26A—C25A—C27A108.5 (3)C21B—C20B—C12B112.52 (19)
C26A—C25A—C24A100.3 (5)C22B—C20B—C12B111.13 (19)
C27A—C25A—C24A100.7 (4)C21B—C20B—H20B107.7
C26A—C25A—H25A115.1C22B—C20B—H20B107.7
C27A—C25A—H25A115.1C12B—C20B—H20B107.7
C24A—C25A—H25A115.1C20B—C21B—H21D109.5
C27A—C25A—H26I117.5C20B—C21B—H21E109.5
C24A—C25A—H26I128.6H21D—C21B—H21E109.5
H25A—C25A—H26I79.4C20B—C21B—H21F109.5
C22A—C23C—C24C108.8 (4)H21D—C21B—H21F109.5
C22A—C23C—H23C109.9H21E—C21B—H21F109.5
C24C—C23C—H23C109.9C23B—C22B—C20B112.4 (2)
C22A—C23C—H23D109.9C23B—C22B—H22C109.1
C24C—C23C—H23D109.9C20B—C22B—H22C109.1
H23C—C23C—H23D108.3C23B—C22B—H22D109.1
C25C—C24C—C23C122.0 (4)C20B—C22B—H22D109.1
C25C—C24C—H24C106.8H22C—C22B—H22D107.8
C23C—C24C—H24C106.8C24B—C23B—C22B116.7 (2)
C25C—C24C—H24D106.8C24B—C23B—H23E108.1
C23C—C24C—H24D106.8C22B—C23B—H23E108.1
H24C—C24C—H24D106.7C24B—C23B—H23F108.1
C24C—C25C—C27A108.1 (4)C22B—C23B—H23F108.1
C24C—C25C—C26A109.9 (4)H23E—C23B—H23F107.3
C27A—C25C—C26A104.2 (3)C25B—C24B—C23B116.1 (2)
C24C—C25C—H25C111.4C25B—C24B—H24E108.3
C27A—C25C—H25C111.4C23B—C24B—H24E108.3
C26A—C25C—H25C111.4C25B—C24B—H24F108.3
C25A—C26A—H26D110.2C23B—C24B—H24F108.3
C25C—C26A—H26D135.7H24E—C24B—H24F107.4
C25A—C26A—H26E109.9C27B—C25B—C26B110.4 (2)
C25C—C26A—H26E111.5C27B—C25B—C24B112.4 (2)
H26D—C26A—H26E107.7C26B—C25B—C24B110.4 (2)
C25A—C26A—H26F110.4C27B—C25B—H25B107.8
C25C—C26A—H26F76.3C26B—C25B—H25B107.8
H26D—C26A—H26F108.9C24B—C25B—H25B107.8
H26E—C26A—H26F109.7C25B—C26B—H26A109.5
C25A—C26A—H26G120.6C25B—C26B—H26B109.5
C25C—C26A—H26G110.4H26A—C26B—H26B109.5
H26D—C26A—H26G113.3C25B—C26B—H26C109.5
H26F—C26A—H26G91.6H26A—C26B—H26C109.5
C25A—C26A—H26H126.2H26B—C26B—H26C109.5
C25C—C26A—H26H110.0C25B—C27B—H27A109.5
H26D—C26A—H26H60.9C25B—C27B—H27B109.5
H26E—C26A—H26H123.5H27A—C27B—H27B109.5
H26F—C26A—H26H48.0C25B—C27B—H27C109.5
H26G—C26A—H26H109.8H27A—C27B—H27C109.5
C25A—C26A—H26I74.0H27B—C27B—H27C109.5
C17A—C1A—N1A—O1A1.6 (3)C27A—C25A—C26A—C25C−64.1 (4)
C2A—C1A—N1A—O1A178.6 (2)C24A—C25A—C26A—C25C41.1 (4)
N1A—C1A—C2A—C3A−2.9 (3)C24C—C25C—C26A—C25A−51.6 (4)
C17A—C1A—C2A—C3A174.4 (2)C27A—C25C—C26A—C25A64.0 (4)
N1A—C1A—C2A—C7A127.3 (2)C24C—C25C—C27A—C25A58.9 (4)
C17A—C1A—C2A—C7A−55.4 (3)C26A—C25C—C27A—C25A−58.0 (4)
C1A—C2A—C3A—C4A−175.2 (2)C26A—C25A—C27A—C25C69.9 (4)
C7A—C2A—C3A—C4A56.6 (3)C24A—C25A—C27A—C25C−34.9 (5)
C2A—C3A—C4A—C5A−57.0 (3)C2B—C1B—N1B—O1B−179.16 (19)
C3A—C4A—C5A—C6A56.6 (3)C17B—C1B—N1B—O1B−2.4 (3)
C4A—C5A—C6A—C7A−55.2 (3)N1B—C1B—C2B—C3B−12.9 (3)
C5A—C6A—C7A—C18A−69.5 (3)C17B—C1B—C2B—C3B169.95 (19)
C5A—C6A—C7A—C8A167.4 (2)N1B—C1B—C2B—C7B116.2 (2)
C5A—C6A—C7A—C2A51.0 (3)C17B—C1B—C2B—C7B−60.9 (2)
C1A—C2A—C7A—C18A−62.4 (3)C1B—C2B—C3B—C4B−174.5 (2)
C3A—C2A—C7A—C18A68.1 (3)C7B—C2B—C3B—C4B58.2 (3)
C1A—C2A—C7A—C6A177.30 (19)C2B—C3B—C4B—C5B−56.1 (3)
C3A—C2A—C7A—C6A−52.3 (3)C3B—C4B—C5B—C6B54.9 (3)
C1A—C2A—C7A—C8A59.0 (2)C4B—C5B—C6B—C7B−55.6 (3)
C3A—C2A—C7A—C8A−170.53 (19)C5B—C6B—C7B—C18B−66.5 (3)
C18A—C7A—C8A—C16A61.3 (2)C5B—C6B—C7B—C8B170.40 (19)
C6A—C7A—C8A—C16A−176.5 (2)C5B—C6B—C7B—C2B53.7 (3)
C2A—C7A—C8A—C16A−59.5 (2)C1B—C2B—C7B—C18B−65.2 (2)
C18A—C7A—C8A—C9A−66.1 (3)C3B—C2B—C7B—C18B64.7 (2)
C6A—C7A—C8A—C9A56.2 (3)C1B—C2B—C7B—C6B174.70 (18)
C2A—C7A—C8A—C9A173.19 (19)C3B—C2B—C7B—C6B−55.4 (2)
C16A—C8A—C9A—C10A55.5 (3)C1B—C2B—C7B—C8B56.5 (2)
C7A—C8A—C9A—C10A−175.6 (2)C3B—C2B—C7B—C8B−173.54 (18)
C8A—C9A—C10A—C11A−55.1 (3)C18B—C7B—C8B—C9B−59.9 (2)
C9A—C10A—C11A—C19A−70.1 (3)C6B—C7B—C8B—C9B62.6 (2)
C9A—C10A—C11A—C15A52.5 (3)C2B—C7B—C8B—C9B178.76 (18)
C9A—C10A—C11A—C12A162.4 (2)C18B—C7B—C8B—C16B66.7 (2)
C10A—C11A—C12A—C20A76.5 (3)C6B—C7B—C8B—C16B−170.81 (19)
C19A—C11A—C12A—C20A−51.2 (3)C2B—C7B—C8B—C16B−54.6 (2)
C15A—C11A—C12A—C20A−168.6 (2)C16B—C8B—C9B—C10B52.2 (2)
C10A—C11A—C12A—C13A−157.6 (2)C7B—C8B—C9B—C10B−179.69 (19)
C19A—C11A—C12A—C13A74.8 (2)C8B—C9B—C10B—C11B−53.8 (3)
C15A—C11A—C12A—C13A−42.7 (2)C9B—C10B—C11B—C19B−66.9 (2)
C20A—C12A—C13A—C14A154.2 (2)C9B—C10B—C11B—C15B55.2 (2)
C11A—C12A—C13A—C14A23.0 (2)C9B—C10B—C11B—C12B166.40 (19)
C12A—C13A—C14A—C15A6.7 (3)C10B—C11B—C12B—C20B80.1 (3)
C13A—C14A—C15A—C16A−164.5 (2)C19B—C11B—C12B—C20B−47.6 (3)
C13A—C14A—C15A—C11A−34.4 (2)C15B—C11B—C12B—C20B−164.89 (19)
C10A—C11A—C15A—C16A−56.6 (3)C10B—C11B—C12B—C13B−155.79 (19)
C19A—C11A—C15A—C16A65.0 (3)C19B—C11B—C12B—C13B76.5 (2)
C12A—C11A—C15A—C16A−179.06 (19)C15B—C11B—C12B—C13B−40.8 (2)
C10A—C11A—C15A—C14A170.8 (2)C20B—C12B—C13B—C14B150.24 (19)
C19A—C11A—C15A—C14A−67.6 (3)C11B—C12B—C13B—C14B21.6 (2)
C12A—C11A—C15A—C14A48.3 (2)C12B—C13B—C14B—C15B6.7 (2)
C14A—C15A—C16A—C8A−175.63 (19)C13B—C14B—C15B—C16B−159.81 (19)
C11A—C15A—C16A—C8A59.2 (2)C13B—C14B—C15B—C11B−33.0 (2)
C14A—C15A—C16A—C17A−53.1 (3)C10B—C11B—C15B—C14B168.70 (18)
C11A—C15A—C16A—C17A−178.32 (19)C19B—C11B—C15B—C14B−69.3 (2)
C9A—C8A—C16A—C15A−55.6 (2)C12B—C11B—C15B—C14B46.3 (2)
C7A—C8A—C16A—C15A174.08 (19)C10B—C11B—C15B—C16B−61.0 (2)
C9A—C8A—C16A—C17A−176.9 (2)C19B—C11B—C15B—C16B61.0 (2)
C7A—C8A—C16A—C17A52.8 (3)C12B—C11B—C15B—C16B176.61 (18)
N1A—C1A—C17A—C16A−135.3 (2)C14B—C15B—C16B—C17B−51.9 (3)
C2A—C1A—C17A—C16A47.7 (3)C11B—C15B—C16B—C17B−174.53 (18)
C15A—C16A—C17A—C1A−165.31 (19)C14B—C15B—C16B—C8B−175.85 (19)
C8A—C16A—C17A—C1A−44.6 (3)C11B—C15B—C16B—C8B61.5 (2)
C11A—C12A—C20A—C21A−55.6 (3)C9B—C8B—C16B—C15B−54.5 (2)
C13A—C12A—C20A—C21A−177.4 (2)C7B—C8B—C16B—C15B177.24 (17)
C11A—C12A—C20A—C22A−178.5 (2)C9B—C8B—C16B—C17B−178.27 (19)
C13A—C12A—C20A—C22A59.8 (3)C7B—C8B—C16B—C17B53.4 (2)
C21A—C20A—C22A—C23C48.0 (4)N1B—C1B—C17B—C16B−119.6 (3)
C12A—C20A—C22A—C23C171.2 (3)C2B—C1B—C17B—C16B57.2 (3)
C21A—C20A—C22A—C23A79.0 (4)C15B—C16B—C17B—C1B−173.77 (18)
C12A—C20A—C22A—C23A−157.8 (3)C8B—C16B—C17B—C1B−51.4 (2)
C23C—C22A—C23A—C24A−82.6 (9)C11B—C12B—C20B—C21B−55.1 (3)
C20A—C22A—C23A—C24A−170.8 (5)C13B—C12B—C20B—C21B−174.8 (2)
C22A—C23A—C24A—C25A90.4 (8)C11B—C12B—C20B—C22B−178.8 (2)
C23A—C24A—C25A—C26A78.9 (7)C13B—C12B—C20B—C22B61.5 (2)
C23A—C24A—C25A—C27A−169.8 (6)C21B—C20B—C22B—C23B73.3 (3)
C20A—C22A—C23C—C24C−177.1 (3)C12B—C20B—C22B—C23B−161.5 (2)
C23A—C22A—C23C—C24C77.1 (7)C20B—C22B—C23B—C24B−171.1 (2)
C22A—C23C—C24C—C25C−156.5 (4)C22B—C23B—C24B—C25B91.1 (3)
C23C—C24C—C25C—C27A−151.5 (4)C23B—C24B—C25B—C27B−71.7 (3)
C23C—C24C—C25C—C26A−38.4 (6)C23B—C24B—C25B—C26B164.5 (2)

Experimental details

Crystal data
Chemical formulaC27H47NO
Mr401.65
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)13.7535 (7), 9.5266 (4), 18.681 (1)
β (°) 102.829 (3)
V (Å3)2386.6 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.54 × 0.31 × 0.17
Data collection
DiffractometerBruker Kappa APEXII Duo
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.965, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		51587, 7706, 6021
Rint0.052
(sin θ/λ)max (Å−1)0.716
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.129, 1.12
No. of reflections7706
No. of parameters564
No. of restraints59
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.48, −0.32

Computer programs: APEX2 (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

 

Acknowledgements

SU, HK and AM thank the Department of Chemistry, Aligarth Muslim University, India, for providing the necessary research facilities. YNM thanks the Deanship of Scientific Research at King Saud University for funding this work through Research Group Project No. RGP-VPP-007. Thanks are extended to Dr Wolfgang Frey, Institut für Organische Chemie, Universität Stuttgart, Germany, for valuable help.

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.  CSD CrossRef Web of Science Google Scholar
 First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGrover, V. K., Babu, R. & Bedi, S. P. S. (2007). Indian J. Anaesth. 51, 389–393.  Google Scholar
 First citationKetuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o773–o774.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPark, Y. J. (2004). Bull. Korean Chem. Soc. 25, 751–753.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShoppee, C. W., Jones, D. N., Lewis, J. R. & Summers, G. H. R. (1955). J. Chem. Soc. pp. 2876–2887.  Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages o3037-o3038
https://doi.org/10.1107/S1600536812040093
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