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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 4| April 2012| Pages o1056-o1057
doi:10.1107/S1600536812009336

3β-Chloro-6-[2-(2-cyano­acet­yl)hydrazin-1-yl­­idene]-5α-cholestane

Samina Khan Yusufzai,a Hasnah Osman,a‡ Aisyah Saad Abdul Rahim,b Suhana Arshadc and Ibrahim Abdul Razakc*§

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 27 February 2012; accepted 2 March 2012; online 14 March 2012)

The asymmetric unit of the title compound, C30H48ClN3O, contains two mol­ecules, A and B. In both mol­ecules, the three cyclo­hexane rings in the steroid fused ring systems adopt chair conformations, while the cyclo­pentane rings adopt envelope and twist conformations in mol­ecules A and B, respectively. In mol­ecule B, the cyano group is disordered over two orientations with refined site-occupancies of 0.593 (8) and 0.407 (8). An intra­molecular C—H⋯N inter­action forms an S(10) ring in both mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O, C—H⋯O and C—H⋯N inter­actions, resulting is chains propagating along the a-axis direction.

Related literature

For related structures, see: Yusufzai et al. (2012[Yusufzai, S. K., Osman, H., Sulaiman, O., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o473-o474.]); Ketuly et al. (2011[Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o773-o774.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C30H48ClN3O

  • Mr = 502.16

  • Orthorhombic, P 21 21 21

  • a = 11.1623 (2) Å

  • b = 19.7586 (3) Å

  • c = 26.4077 (4) Å

  • V = 5824.26 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 100 K

  • 0.32 × 0.32 × 0.16 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.976

  • 51504 measured reflections

  • 13243 independent reflections

  • 12103 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.104

  • wR(F2) = 0.221

  • S = 1.18

  • 13243 reflections

  • 655 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.52 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5882 Friedel pairs

  • Flack parameter: 0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4B—H4BA⋯N3B 0.99 2.58 3.469 (10) 149
N2A—H1NA⋯O1Bi 0.85 2.03 2.870 (6) 168
N2B—H1NB⋯O1Aii 0.85 2.05 2.894 (6) 171
C1A—H1AB⋯O1Bi 0.99 2.41 3.362 (7) 162
C1B—H1BB⋯O1Aii 0.99 2.44 3.352 (6) 153
C4A—H4AB⋯N3Biii 0.99 2.49 3.476 (9) 173
C19A—H19A⋯N3Biii 0.99 2.57 3.513 (11) 160
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009336/hb6661sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009336/hb6661Isup2.hkl

checkCIF report


Comment top

The study being reported in this paper is a part of our on going effort towards the synthesis of modified steroids, which may be biologically active. In continuation of our previous work (Yusufzai et al., 2012) we report the synthesis of 3β-chloro-6-[2-(2-cyanoacetyl)hydrazin-1-ylidene]-5α-cholestane which corresponds to the molecular formula, C30H48N3OCl.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules A and B. The bond lengths are comparable to those in related structures (Yusufzai et al., 2012; Ketuly et al., 2011). In molecule B, the nitrile group is disordered over two positions with refined site-occupancies of 0.593 (8): 0.407 (8) ratio. The cyclopentane ring of the steroid fused ring system in both molecules adopts a different ring conformation (Cremer & Pople, 1975). In molecule A, it is in twist conformation where the cyclopentane (C12A–C16A) ring is twisted about C16A–C12A bonds, with puckering parameters Q= 0.472 (6) Å and φ= 348.8 (8)°. Meanwhile, the cyclopentane (C12B–C16B) ring of molecule B is in envelope conformation with puckering parameters Q= 0.456 (5) Å and φ= 353.6 (7)° with atom C12B at the flap. In addition, the three cyclohexane rings in the steroid fused ring system for both molecules adopt a chair conformation [Molecule A (C1A–C3A/C8A/C9A/C17A):(C3A–C8A):(C9A–C12A/C16A/C17A); Q= 0.583 (6):0.562 (3):0.588 (6) Å, Θ= 172.4 (6):178.7 (3):175.7 (6)° and Φ= 305 (4):232 (10):120 (8)°; Molecule B (C1B–C3B/C8B/C9B/C17B): (C3B–C8B):(C9B–C12B/C16B/C17B); Q= 0.549 (6):0.595 (6):0.568 (5) Å, Θ= 172.2 (6):178.9 (6):174.7 (5)° and Φ= 30 (4):258 (23):31 (6)°]. Furthermore, an intramolecular C4B—H4BA···N3B hydrogen bond is observed in B and forms an S(10) ring motif (Bernstein et al., 1995).

There are nine chiral centres presented in molecule A and B. In each molecules, the centers exhibit the following relative chiralities: C3A/C3B = S; C5A/C5B = S; C8A/C8B = R; C9A/C9B = S; C12A/C12B = R; C13A/C13B = R; C16A/C16B = S; C17A/C17B = S and C24A/C24B = R.

The crystal packing is shown in Fig. 2. N—H···O (Table 1) hydrogen bonds generate R22(8) ring motifs, sandwiched by two R12(7) ring motifs when combined with C—H···O (Table 1) hydrogen bonds. In addition, C—H···N (Table 1) interactions form R12(10) ring motifs. These ring motifs link the molecules into chains along a-axis.

Related literature top

For related structures, see: Yusufzai et al. (2012); Ketuly et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of steroidal ketone 3β-chloro-5α-cholestan-6-one (5 mmol), in absolute ethanol (10 ml) was added cyanoacetohydrazide (10 mmol) followed by few drops of triethylamine. The reaction mixture was refluxed for 24 hrs. The progress of reaction was monitored by thin layer chromatography. After completion of reaction, reaction mixture was concentrated under reduce pressure. The obtained solid, was extracted with ether and ethereal layer was washed with water, NaHCO3 solution (5%), again with water and dried over anhydrous sodium sulfate. The solvent was evaporated and the product was recrystallized from ethanol to give compound as colourless blocks.

Refinement top

The nitrile group of molecule B was disordered over two positions with refined site-occupancies of 0.593 (8): 0.407 (8) ratio. N-bound H atoms was located from the difference fourier map and was fixed at its found location using riding model with Uiso(H) = 1.5 Ueq(N) [N–H = 0.8537 and 0.8549 Å]. The remaining H atoms were positioned geometrically [C–H = 0.98–1.0 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. The same Uij parameters were used for atoms pair C28A and C29A. 5882 Friedel pairs were used to determine the absolute configuration.

Structure description top

The study being reported in this paper is a part of our on going effort towards the synthesis of modified steroids, which may be biologically active. In continuation of our previous work (Yusufzai et al., 2012) we report the synthesis of 3β-chloro-6-[2-(2-cyanoacetyl)hydrazin-1-ylidene]-5α-cholestane which corresponds to the molecular formula, C30H48N3OCl.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules A and B. The bond lengths are comparable to those in related structures (Yusufzai et al., 2012; Ketuly et al., 2011). In molecule B, the nitrile group is disordered over two positions with refined site-occupancies of 0.593 (8): 0.407 (8) ratio. The cyclopentane ring of the steroid fused ring system in both molecules adopts a different ring conformation (Cremer & Pople, 1975). In molecule A, it is in twist conformation where the cyclopentane (C12A–C16A) ring is twisted about C16A–C12A bonds, with puckering parameters Q= 0.472 (6) Å and φ= 348.8 (8)°. Meanwhile, the cyclopentane (C12B–C16B) ring of molecule B is in envelope conformation with puckering parameters Q= 0.456 (5) Å and φ= 353.6 (7)° with atom C12B at the flap. In addition, the three cyclohexane rings in the steroid fused ring system for both molecules adopt a chair conformation [Molecule A (C1A–C3A/C8A/C9A/C17A):(C3A–C8A):(C9A–C12A/C16A/C17A); Q= 0.583 (6):0.562 (3):0.588 (6) Å, Θ= 172.4 (6):178.7 (3):175.7 (6)° and Φ= 305 (4):232 (10):120 (8)°; Molecule B (C1B–C3B/C8B/C9B/C17B): (C3B–C8B):(C9B–C12B/C16B/C17B); Q= 0.549 (6):0.595 (6):0.568 (5) Å, Θ= 172.2 (6):178.9 (6):174.7 (5)° and Φ= 30 (4):258 (23):31 (6)°]. Furthermore, an intramolecular C4B—H4BA···N3B hydrogen bond is observed in B and forms an S(10) ring motif (Bernstein et al., 1995).

There are nine chiral centres presented in molecule A and B. In each molecules, the centers exhibit the following relative chiralities: C3A/C3B = S; C5A/C5B = S; C8A/C8B = R; C9A/C9B = S; C12A/C12B = R; C13A/C13B = R; C16A/C16B = S; C17A/C17B = S and C24A/C24B = R.

The crystal packing is shown in Fig. 2. N—H···O (Table 1) hydrogen bonds generate R22(8) ring motifs, sandwiched by two R12(7) ring motifs when combined with C—H···O (Table 1) hydrogen bonds. In addition, C—H···N (Table 1) interactions form R12(10) ring motifs. These ring motifs link the molecules into chains along a-axis.

For related structures, see: Yusufzai et al. (2012); Ketuly et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H-atoms are omitted for clarity. Disordered components are shown.
[Figure 2] Fig. 2. The crystal packing of the title compound. Only major disordered components is shown.
3β-Chloro-6-[2-(2-cyanoacetyl)hydrazin-1-ylidene]-5α-cholestane top
Crystal data top
C30H48ClN3OF(000) = 2192
Mr = 502.16Dx = 1.145 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9967 reflections
a = 11.1623 (2) Åθ = 2.2–28.1°
b = 19.7586 (3) ŵ = 0.16 mm−1
c = 26.4077 (4) ÅT = 100 K
V = 5824.26 (16) Å3Block, colourless
Z = 80.32 × 0.32 × 0.16 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		13243 independent reflections
Radiation source: fine-focus sealed tube12103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −14→14
Tmin = 0.951, Tmax = 0.976k = −25→25
51504 measured reflectionsl = −34→34
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.104 w = 1/[σ2(Fo2) + (0.P)2 + 25.2717P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.221(Δ/σ)max < 0.001
S = 1.18Δρmax = 0.50 e Å−3
13243 reflectionsΔρmin = −0.52 e Å−3
655 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00130 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 5882 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.05 (11)
Crystal data top
C30H48ClN3OV = 5824.26 (16) Å3
Mr = 502.16Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.1623 (2) ŵ = 0.16 mm−1
b = 19.7586 (3) ÅT = 100 K
c = 26.4077 (4) Å0.32 × 0.32 × 0.16 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		13243 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		12103 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.976Rint = 0.042
51504 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.104H-atom parameters constrained
wR(F2) = 0.221 w = 1/[σ2(Fo2) + (0.P)2 + 25.2717P]
where P = (Fo2 + 2Fc2)/3
S = 1.18Δρmax = 0.50 e Å−3
13243 reflectionsΔρmin = −0.52 e Å−3
655 parametersAbsolute structure: Flack (1983), 5882 Friedel pairs
0 restraintsAbsolute structure parameter: 0.05 (11)
Special details top

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

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A−0.04761 (13)0.83894 (7)0.25082 (6)0.0339 (3)
O1A0.5580 (3)1.06640 (17)0.20162 (15)0.0272 (8)
N1A0.3929 (4)0.9157 (2)0.20369 (15)0.0195 (8)
N2A0.4907 (4)0.9587 (2)0.19816 (16)0.0218 (9)
H1NA0.55960.94650.18740.033*
N3A0.3345 (5)1.1702 (3)0.2533 (2)0.0450 (15)
C1A0.5176 (5)0.8138 (3)0.18260 (18)0.0233 (11)
H1AA0.53570.78010.20920.028*
H1AB0.58630.84530.18010.028*
C2A0.4073 (5)0.8523 (2)0.19657 (17)0.0187 (10)
C3A0.2960 (5)0.8082 (2)0.19943 (18)0.0216 (10)
H3AA0.31470.76950.22250.026*
C4A0.1858 (5)0.8447 (2)0.22126 (18)0.0218 (10)
H4AA0.20510.86290.25520.026*
H4AB0.16380.88320.19910.026*
C5A0.0813 (5)0.7960 (3)0.2252 (2)0.0266 (12)
H5AA0.10390.75800.24830.032*
C6A0.0511 (6)0.7672 (3)0.1733 (2)0.0306 (13)
H6AA0.02520.80410.15050.037*
H6AB−0.01570.73450.17640.037*
C7A0.1618 (5)0.7316 (3)0.1510 (2)0.0316 (13)
H7AA0.18310.69280.17290.038*
H7AB0.14080.71340.11720.038*
C8A0.2721 (5)0.7778 (3)0.14556 (18)0.0250 (12)
C9A0.3842 (5)0.7368 (3)0.1301 (2)0.0264 (12)
H9AA0.39340.70010.15590.032*
C10A0.3716 (6)0.7015 (3)0.0785 (2)0.0405 (16)
H10A0.36370.73610.05160.049*
H10B0.29800.67360.07840.049*
C11A0.4810 (6)0.6560 (3)0.0670 (2)0.0434 (17)
H11A0.48250.61820.09160.052*
H11B0.47140.63630.03280.052*
C12A0.6011 (5)0.6934 (2)0.06944 (17)0.0221 (11)
C13A0.7141 (7)0.6488 (3)0.0738 (2)0.0394 (16)
H13A0.69500.61220.09870.047*
C14A0.8061 (6)0.6973 (3)0.1001 (2)0.0358 (14)
H14A0.85370.67230.12570.043*
H14B0.86160.71690.07480.043*
C15A0.7304 (6)0.7543 (3)0.1260 (2)0.0340 (13)
H15A0.75340.75990.16200.041*
H15B0.74070.79810.10830.041*
C16A0.6038 (6)0.7290 (2)0.12135 (19)0.0275 (12)
H16A0.59580.69220.14710.033*
C17A0.4992 (5)0.7774 (2)0.13125 (18)0.0214 (10)
H17A0.49670.81200.10370.026*
C18A0.4770 (5)1.0254 (2)0.20651 (19)0.0209 (10)
C19A0.3534 (5)1.0449 (3)0.2252 (2)0.0300 (13)
H19A0.29421.03610.19810.036*
H19B0.33211.01630.25460.036*
C20A0.3463 (5)1.1162 (3)0.2400 (2)0.0316 (13)
C21A0.2448 (5)0.8344 (3)0.10696 (18)0.0277 (12)
H21A0.21480.81430.07550.042*
H21B0.31830.85990.09990.042*
H21C0.18420.86500.12100.042*
C22A0.6114 (5)0.7438 (3)0.02495 (19)0.0275 (12)
H22A0.54970.77880.02830.041*
H22B0.60010.7196−0.00710.041*
H22C0.69080.76490.02540.041*
C23A0.6780 (7)0.5678 (3)0.0007 (2)0.0429 (17)
H23A0.71970.5419−0.02560.064*
H23B0.61460.5951−0.01480.064*
H23C0.64250.53650.02530.064*
C24A0.7676 (6)0.6144 (3)0.02777 (19)0.0294 (12)
H24A0.79290.65040.00340.035*
C25A0.8795 (7)0.5741 (3)0.0433 (2)0.0374 (15)
H25A0.85420.53740.06640.045*
H25B0.93290.60460.06270.045*
C26A0.9527 (6)0.5425 (3)0.0000 (2)0.0325 (13)
H26A0.90390.5072−0.01680.039*
H26B0.97140.5778−0.02540.039*
C27A1.0694 (7)0.5109 (3)0.0189 (2)0.0410 (16)
H27A1.11610.54630.03670.049*
H27B1.04950.47550.04410.049*
C28A1.1483 (6)0.4797 (3)−0.0216 (3)0.0432 (12)
H28A1.16480.5150−0.04780.052*
C29A1.2657 (6)0.4581 (3)0.0009 (3)0.0432 (12)
H29A1.30550.49740.01620.065*
H29B1.31690.4392−0.02570.065*
H29C1.25150.42380.02700.065*
C30A1.0869 (7)0.4199 (3)−0.0476 (2)0.0413 (16)
H30A1.13920.4021−0.07420.062*
H30B1.01110.4349−0.06250.062*
H30C1.07120.3843−0.02260.062*
Cl1B−0.30342 (14)0.65408 (10)0.42098 (10)0.0666 (7)
O1B0.2818 (4)0.43353 (19)0.34895 (17)0.0319 (9)
N1B0.1279 (4)0.5859 (2)0.36554 (19)0.0276 (10)
N2B0.2194 (4)0.5423 (2)0.35160 (18)0.0240 (9)
H1NB0.28050.54960.33290.036*
N3B−0.1078 (8)0.4889 (4)0.3466 (3)0.036 (2)0.593 (8)
C20B−0.0208 (9)0.4748 (4)0.3670 (4)0.027 (2)0.593 (8)
N3X0.1102 (11)0.3588 (6)0.4478 (4)0.033 (3)0.407 (8)
C20X0.1042 (12)0.3992 (6)0.4172 (5)0.024 (3)0.407 (8)
C1B0.2503 (4)0.6858 (2)0.3379 (2)0.0232 (11)
H1BA0.23360.69970.30260.028*
H1BB0.31940.65440.33740.028*
C2B0.1429 (4)0.6494 (3)0.3588 (2)0.0246 (11)
C3B0.0363 (5)0.6942 (3)0.3708 (2)0.0317 (13)
H3BA0.01080.71420.33780.038*
C4B−0.0719 (5)0.6534 (3)0.3899 (3)0.0378 (15)
H4BA−0.09100.61660.36580.045*
H4BB−0.05340.63280.42320.045*
C5B−0.1784 (6)0.7016 (3)0.3948 (3)0.0460 (19)
H5BA−0.20090.71840.36040.055*
C6B−0.1530 (5)0.7614 (3)0.4286 (2)0.0364 (15)
H6BA−0.14020.74560.46370.044*
H6BB−0.22280.79230.42850.044*
C7B−0.0414 (5)0.7996 (3)0.4102 (2)0.0300 (12)
H7BA−0.05930.82070.37710.036*
H7BB−0.02330.83640.43450.036*
C8B0.0696 (5)0.7547 (3)0.4047 (2)0.0275 (11)
C9B0.1736 (5)0.7944 (2)0.3787 (2)0.0222 (11)
H9BA0.14330.80780.34450.027*
C10B0.2100 (5)0.8608 (2)0.4055 (2)0.0232 (10)
H10C0.13980.89140.40670.028*
H10D0.23310.85030.44090.028*
C11B0.3148 (5)0.8978 (2)0.3793 (2)0.0249 (11)
H11C0.28780.91450.34580.030*
H11D0.33810.93760.39990.030*
C12B0.4238 (5)0.8522 (2)0.37214 (18)0.0215 (10)
C13B0.5244 (5)0.8768 (2)0.33587 (19)0.0228 (11)
H13B0.48440.89580.30510.027*
C14B0.5878 (5)0.8101 (3)0.3195 (2)0.0248 (11)
H14C0.61230.81260.28350.030*
H14D0.65990.80210.34050.030*
C15B0.4952 (5)0.7525 (3)0.3274 (2)0.0264 (11)
H15C0.48310.72660.29570.032*
H15D0.52170.72110.35430.032*
C16B0.3805 (5)0.7892 (2)0.34283 (18)0.0181 (10)
H16B0.34400.80650.31080.022*
C17B0.2834 (5)0.7489 (2)0.36931 (19)0.0203 (10)
H17B0.31500.73360.40280.024*
C18B0.2049 (5)0.4753 (3)0.3603 (2)0.0253 (11)
C19B0.0894 (5)0.4542 (3)0.3861 (3)0.0385 (15)
H19C0.08860.40410.38720.046*0.593 (8)
H19D0.09390.47010.42160.046*0.593 (8)
H19E0.05860.49260.40630.046*0.407 (8)
H19F0.02890.44320.35990.046*0.407 (8)
C21B0.1082 (6)0.7304 (3)0.4578 (2)0.0390 (15)
H21D0.03920.71040.47520.058*
H21E0.13820.76890.47740.058*
H21F0.17160.69640.45440.058*
C22B0.4781 (5)0.8330 (3)0.42409 (19)0.0287 (12)
H22D0.50270.87420.44190.043*
H22E0.54800.80380.41900.043*
H22F0.41810.80890.44430.043*
C23B0.5555 (6)0.9928 (3)0.3767 (3)0.0383 (14)
H23D0.61581.02830.38140.057*
H23E0.51960.98140.40950.057*
H23F0.49301.00900.35360.057*
C24B0.6150 (5)0.9299 (3)0.3543 (2)0.0255 (11)
H24B0.66500.90860.38140.031*
C25B0.6988 (5)0.9511 (3)0.3109 (2)0.0275 (12)
H25C0.72110.91020.29130.033*
H25D0.65440.98160.28780.033*
C26B0.8134 (5)0.9867 (3)0.3278 (2)0.0272 (12)
H26C0.79401.01900.35530.033*
H26D0.86990.95280.34160.033*
C27B0.8733 (5)1.0243 (2)0.2851 (2)0.0227 (11)
H27C0.81501.05680.27060.027*
H27D0.89420.99150.25820.027*
C28B0.9876 (5)1.0635 (2)0.3002 (2)0.0272 (12)
H28B0.96791.09210.33030.033*
C29B1.0886 (5)1.0163 (3)0.3150 (3)0.0368 (14)
H29D1.06520.99040.34500.055*
H29E1.16051.04290.32250.055*
H29F1.10530.98520.28700.055*
C30B1.0274 (5)1.1102 (3)0.2579 (2)0.0329 (13)
H30D0.95901.13720.24640.049*
H30E1.05841.08320.22970.049*
H30F1.09051.14040.27040.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0317 (7)0.0336 (7)0.0364 (7)−0.0058 (6)0.0101 (6)−0.0085 (6)
O1A0.0176 (18)0.0201 (17)0.044 (2)−0.0037 (15)0.0072 (17)−0.0058 (16)
N1A0.020 (2)0.0201 (19)0.0183 (19)−0.0047 (17)0.0031 (17)−0.0016 (15)
N2A0.018 (2)0.0204 (19)0.026 (2)−0.0060 (17)0.0053 (18)−0.0007 (16)
N3A0.034 (3)0.031 (3)0.070 (4)−0.013 (2)0.031 (3)−0.017 (3)
C1A0.030 (3)0.023 (2)0.017 (2)0.003 (2)0.003 (2)0.0035 (18)
C2A0.026 (3)0.017 (2)0.013 (2)−0.002 (2)−0.0014 (19)−0.0022 (17)
C3A0.031 (3)0.019 (2)0.015 (2)−0.006 (2)0.004 (2)−0.0085 (18)
C4A0.029 (3)0.019 (2)0.017 (2)−0.006 (2)0.005 (2)−0.0017 (18)
C5A0.032 (3)0.022 (2)0.025 (3)−0.005 (2)0.009 (2)−0.001 (2)
C6A0.031 (3)0.031 (3)0.030 (3)−0.017 (3)0.013 (3)−0.007 (2)
C7A0.029 (3)0.026 (3)0.040 (3)−0.017 (2)0.009 (3)−0.009 (2)
C8A0.030 (3)0.029 (3)0.016 (2)−0.016 (2)0.011 (2)−0.014 (2)
C9A0.024 (3)0.022 (2)0.032 (3)−0.009 (2)0.008 (2)−0.009 (2)
C10A0.032 (3)0.049 (4)0.041 (3)−0.020 (3)0.018 (3)−0.029 (3)
C11A0.050 (4)0.038 (3)0.042 (3)−0.015 (3)0.026 (3)−0.028 (3)
C12A0.033 (3)0.022 (2)0.011 (2)−0.002 (2)0.004 (2)−0.0059 (18)
C13A0.070 (5)0.023 (3)0.026 (3)0.011 (3)0.020 (3)0.000 (2)
C14A0.040 (4)0.034 (3)0.033 (3)0.018 (3)−0.003 (3)−0.013 (2)
C15A0.036 (3)0.032 (3)0.035 (3)0.004 (3)−0.006 (3)−0.013 (2)
C16A0.046 (4)0.017 (2)0.019 (2)−0.008 (2)0.011 (2)−0.0007 (19)
C17A0.027 (3)0.020 (2)0.018 (2)−0.005 (2)0.005 (2)−0.0011 (18)
C18A0.020 (3)0.020 (2)0.022 (2)−0.004 (2)0.002 (2)0.0003 (18)
C19A0.021 (3)0.020 (2)0.048 (3)−0.009 (2)0.009 (3)−0.010 (2)
C20A0.020 (3)0.030 (3)0.045 (3)−0.012 (2)0.020 (3)−0.009 (2)
C21A0.034 (3)0.033 (3)0.016 (2)−0.011 (2)0.006 (2)−0.005 (2)
C22A0.030 (3)0.028 (3)0.025 (3)0.002 (2)0.004 (2)−0.002 (2)
C23A0.059 (5)0.029 (3)0.041 (3)−0.016 (3)0.023 (3)−0.017 (3)
C24A0.044 (4)0.027 (3)0.018 (2)−0.001 (3)0.005 (2)−0.001 (2)
C25A0.060 (4)0.033 (3)0.019 (3)0.010 (3)0.003 (3)−0.004 (2)
C26A0.047 (4)0.031 (3)0.019 (2)0.014 (3)0.008 (3)0.000 (2)
C27A0.061 (5)0.038 (3)0.024 (3)0.019 (3)−0.010 (3)−0.001 (2)
C28A0.043 (3)0.043 (2)0.044 (3)0.024 (2)−0.010 (2)−0.013 (2)
C29A0.043 (3)0.043 (2)0.044 (3)0.024 (2)−0.010 (2)−0.013 (2)
C30A0.057 (5)0.036 (3)0.031 (3)0.007 (3)0.011 (3)−0.011 (3)
Cl1B0.0194 (7)0.0534 (10)0.1270 (19)0.0128 (8)0.0330 (10)0.0390 (12)
O1B0.021 (2)0.0231 (18)0.052 (3)0.0050 (16)0.0054 (19)0.0013 (17)
N1B0.012 (2)0.024 (2)0.047 (3)0.0063 (18)0.004 (2)0.005 (2)
N2B0.014 (2)0.020 (2)0.038 (2)−0.0005 (17)0.0044 (19)0.0048 (18)
N3B0.036 (5)0.030 (4)0.042 (5)−0.012 (4)−0.003 (4)−0.009 (4)
C20B0.023 (5)0.023 (4)0.035 (5)−0.002 (4)0.005 (4)−0.004 (4)
N3X0.031 (7)0.044 (7)0.022 (5)−0.006 (6)0.000 (5)0.017 (5)
C20X0.027 (7)0.025 (6)0.020 (6)−0.003 (5)0.014 (5)−0.011 (5)
C1B0.009 (2)0.017 (2)0.043 (3)0.0037 (18)0.010 (2)0.000 (2)
C2B0.007 (2)0.024 (2)0.043 (3)0.006 (2)0.010 (2)0.008 (2)
C3B0.021 (3)0.021 (2)0.053 (4)0.008 (2)0.012 (3)0.011 (2)
C4B0.015 (3)0.037 (3)0.062 (4)0.015 (2)0.016 (3)0.023 (3)
C5B0.025 (3)0.036 (3)0.078 (5)0.014 (3)0.027 (3)0.024 (3)
C6B0.022 (3)0.043 (3)0.044 (3)0.016 (3)0.020 (3)0.018 (3)
C7B0.024 (3)0.031 (3)0.035 (3)0.015 (2)0.011 (2)0.008 (2)
C8B0.021 (3)0.035 (3)0.027 (3)0.007 (2)0.008 (2)0.008 (2)
C9B0.025 (3)0.018 (2)0.024 (2)0.008 (2)0.005 (2)0.0039 (19)
C10B0.021 (3)0.024 (2)0.025 (2)0.007 (2)0.004 (2)−0.002 (2)
C11B0.034 (3)0.019 (2)0.022 (2)0.009 (2)−0.002 (2)−0.0027 (19)
C12B0.031 (3)0.017 (2)0.016 (2)0.006 (2)0.000 (2)−0.0022 (18)
C13B0.027 (3)0.019 (2)0.022 (2)−0.005 (2)−0.002 (2)0.0018 (18)
C14B0.023 (3)0.027 (3)0.025 (2)−0.006 (2)0.008 (2)−0.007 (2)
C15B0.021 (3)0.020 (2)0.038 (3)−0.001 (2)0.014 (2)−0.002 (2)
C16B0.023 (3)0.014 (2)0.018 (2)0.0027 (19)0.002 (2)0.0004 (17)
C17B0.019 (2)0.018 (2)0.024 (2)0.007 (2)0.005 (2)0.0025 (19)
C18B0.017 (2)0.022 (2)0.037 (3)0.002 (2)−0.003 (2)0.005 (2)
C19B0.019 (3)0.026 (3)0.070 (4)−0.001 (2)0.011 (3)0.016 (3)
C21B0.025 (3)0.050 (4)0.042 (3)0.006 (3)0.010 (3)0.023 (3)
C22B0.026 (3)0.041 (3)0.019 (2)0.005 (2)0.005 (2)0.005 (2)
C23B0.037 (3)0.026 (3)0.052 (4)−0.006 (3)0.002 (3)−0.011 (3)
C24B0.028 (3)0.021 (2)0.028 (3)−0.010 (2)0.003 (2)−0.003 (2)
C25B0.030 (3)0.029 (3)0.024 (3)−0.004 (2)−0.005 (2)0.004 (2)
C26B0.023 (3)0.032 (3)0.027 (3)0.001 (2)−0.004 (2)0.000 (2)
C27B0.019 (3)0.018 (2)0.030 (3)−0.001 (2)−0.007 (2)0.0033 (19)
C28B0.021 (3)0.018 (2)0.043 (3)0.003 (2)0.004 (2)0.000 (2)
C29B0.020 (3)0.043 (3)0.048 (4)0.008 (3)0.004 (3)−0.011 (3)
C30B0.023 (3)0.022 (2)0.054 (4)0.001 (2)0.006 (3)0.000 (2)
Geometric parameters (Å, º) top
Cl1A—C5A1.803 (6)N1B—C2B1.279 (7)
O1A—C18A1.221 (6)N1B—N2B1.385 (6)
N1A—C2A1.277 (6)N2B—C18B1.354 (6)
N1A—N2A1.391 (6)N2B—H1NB0.8549
N2A—C18A1.345 (6)N3B—C20B1.145 (13)
N2A—H1NA0.8537C20B—C19B1.390 (11)
N3A—C20A1.130 (7)N3X—C20X1.138 (17)
C1A—C2A1.493 (7)C20X—C19B1.372 (14)
C1A—C17A1.549 (7)C1B—C2B1.503 (7)
C1A—H1AA0.9900C1B—C17B1.542 (7)
C1A—H1AB0.9900C1B—H1BA0.9900
C2A—C3A1.519 (7)C1B—H1BB0.9900
C3A—C4A1.538 (7)C2B—C3B1.517 (7)
C3A—C8A1.567 (6)C3B—C4B1.537 (7)
C3A—H3AA1.0000C3B—C8B1.537 (8)
C4A—C5A1.516 (7)C3B—H3BA1.0000
C4A—H4AA0.9900C4B—C5B1.529 (7)
C4A—H4AB0.9900C4B—H4BA0.9900
C5A—C6A1.520 (7)C4B—H4BB0.9900
C5A—H5AA1.0000C5B—C6B1.507 (10)
C6A—C7A1.541 (8)C5B—H5BA1.0000
C6A—H6AA0.9900C6B—C7B1.534 (8)
C6A—H6AB0.9900C6B—H6BA0.9900
C7A—C8A1.539 (7)C6B—H6BB0.9900
C7A—H7AA0.9900C7B—C8B1.531 (7)
C7A—H7AB0.9900C7B—H7BA0.9900
C8A—C21A1.543 (8)C7B—H7BB0.9900
C8A—C9A1.545 (8)C8B—C21B1.544 (8)
C9A—C17A1.515 (7)C8B—C9B1.561 (7)
C9A—C10A1.536 (7)C9B—C17B1.540 (7)
C9A—H9AA1.0000C9B—C10B1.546 (7)
C10A—C11A1.547 (9)C9B—H9BA1.0000
C10A—H10A0.9900C10B—C11B1.544 (7)
C10A—H10B0.9900C10B—H10C0.9900
C11A—C12A1.532 (8)C10B—H10D0.9900
C11A—H11A0.9900C11B—C12B1.526 (7)
C11A—H11B0.9900C11B—H11C0.9900
C12A—C16A1.541 (6)C11B—H11D0.9900
C12A—C13A1.543 (8)C12B—C16B1.542 (6)
C12A—C22A1.544 (7)C12B—C22B1.547 (7)
C13A—C24A1.516 (7)C12B—C13B1.555 (7)
C13A—C14A1.568 (9)C13B—C24B1.535 (7)
C13A—H13A1.0000C13B—C14B1.557 (7)
C14A—C15A1.566 (7)C13B—H13B1.0000
C14A—H14A0.9900C14B—C15B1.552 (7)
C14A—H14B0.9900C14B—H14C0.9900
C15A—C16A1.504 (9)C14B—H14D0.9900
C15A—H15A0.9900C15B—C16B1.527 (7)
C15A—H15B0.9900C15B—H15C0.9900
C16A—C17A1.531 (8)C15B—H15D0.9900
C16A—H16A1.0000C16B—C17B1.516 (7)
C17A—H17A1.0000C16B—H16B1.0000
C18A—C19A1.516 (7)C17B—H17B1.0000
C19A—C20A1.463 (7)C18B—C19B1.517 (8)
C19A—H19A0.9900C19B—H19C0.9900
C19A—H19B0.9900C19B—H19D0.9900
C21A—H21A0.9800C19B—H19E0.9900
C21A—H21B0.9800C19B—H19F0.9900
C21A—H21C0.9800C21B—H21D0.9800
C22A—H22A0.9800C21B—H21E0.9800
C22A—H22B0.9800C21B—H21F0.9800
C22A—H22C0.9800C22B—H22D0.9800
C23A—C24A1.537 (8)C22B—H22E0.9800
C23A—H23A0.9800C22B—H22F0.9800
C23A—H23B0.9800C23B—C24B1.528 (8)
C23A—H23C0.9800C23B—H23D0.9800
C24A—C25A1.536 (9)C23B—H23E0.9800
C24A—H24A1.0000C23B—H23F0.9800
C25A—C26A1.537 (8)C24B—C25B1.538 (7)
C25A—H25A0.9900C24B—H24B1.0000
C25A—H25B0.9900C25B—C26B1.528 (8)
C26A—C27A1.528 (9)C25B—H25C0.9900
C26A—H26A0.9900C25B—H25D0.9900
C26A—H26B0.9900C26B—C27B1.507 (7)
C27A—C28A1.517 (9)C26B—H26C0.9900
C27A—H27A0.9900C26B—H26D0.9900
C27A—H27B0.9900C27B—C28B1.544 (7)
C28A—C29A1.501 (9)C27B—H27C0.9900
C28A—C30A1.529 (9)C27B—H27D0.9900
C28A—H28A1.0000C28B—C30B1.514 (8)
C29A—H29A0.9800C28B—C29B1.514 (8)
C29A—H29B0.9800C28B—H28B1.0000
C29A—H29C0.9800C29B—H29D0.9800
C30A—H30A0.9800C29B—H29E0.9800
C30A—H30B0.9800C29B—H29F0.9800
C30A—H30C0.9800C30B—H30D0.9800
Cl1B—C5B1.818 (6)C30B—H30E0.9800
O1B—C18B1.227 (6)C30B—H30F0.9800
C2A—N1A—N2A119.0 (4)N3B—C20B—C19B172.9 (10)
C18A—N2A—N1A119.4 (4)N3X—C20X—C19B171.0 (13)
C18A—N2A—H1NA115.6C2B—C1B—C17B112.4 (4)
N1A—N2A—H1NA124.7C2B—C1B—H1BA109.1
C2A—C1A—C17A110.1 (4)C17B—C1B—H1BA109.1
C2A—C1A—H1AA109.6C2B—C1B—H1BB109.1
C17A—C1A—H1AA109.6C17B—C1B—H1BB109.1
C2A—C1A—H1AB109.6H1BA—C1B—H1BB107.9
C17A—C1A—H1AB109.6N1B—C2B—C1B128.7 (4)
H1AA—C1A—H1AB108.2N1B—C2B—C3B116.2 (4)
N1A—C2A—C1A129.7 (5)C1B—C2B—C3B115.1 (4)
N1A—C2A—C3A116.9 (5)C2B—C3B—C4B112.2 (4)
C1A—C2A—C3A113.2 (4)C2B—C3B—C8B112.7 (5)
C2A—C3A—C4A113.7 (4)C4B—C3B—C8B114.0 (5)
C2A—C3A—C8A108.3 (4)C2B—C3B—H3BA105.7
C4A—C3A—C8A112.6 (4)C4B—C3B—H3BA105.7
C2A—C3A—H3AA107.3C8B—C3B—H3BA105.7
C4A—C3A—H3AA107.3C5B—C4B—C3B108.2 (5)
C8A—C3A—H3AA107.3C5B—C4B—H4BA110.1
C5A—C4A—C3A110.0 (4)C3B—C4B—H4BA110.1
C5A—C4A—H4AA109.7C5B—C4B—H4BB110.1
C3A—C4A—H4AA109.7C3B—C4B—H4BB110.1
C5A—C4A—H4AB109.7H4BA—C4B—H4BB108.4
C3A—C4A—H4AB109.7C6B—C5B—C4B113.1 (6)
H4AA—C4A—H4AB108.2C6B—C5B—Cl1B109.0 (5)
C4A—C5A—C6A110.3 (4)C4B—C5B—Cl1B107.9 (4)
C4A—C5A—Cl1A109.9 (4)C6B—C5B—H5BA108.9
C6A—C5A—Cl1A109.7 (4)C4B—C5B—H5BA108.9
C4A—C5A—H5AA108.9Cl1B—C5B—H5BA108.9
C6A—C5A—H5AA108.9C5B—C6B—C7B110.6 (5)
Cl1A—C5A—H5AA108.9C5B—C6B—H6BA109.5
C5A—C6A—C7A109.8 (5)C7B—C6B—H6BA109.5
C5A—C6A—H6AA109.7C5B—C6B—H6BB109.5
C7A—C6A—H6AA109.7C7B—C6B—H6BB109.5
C5A—C6A—H6AB109.7H6BA—C6B—H6BB108.1
C7A—C6A—H6AB109.7C8B—C7B—C6B113.7 (4)
H6AA—C6A—H6AB108.2C8B—C7B—H7BA108.8
C8A—C7A—C6A114.0 (4)C6B—C7B—H7BA108.8
C8A—C7A—H7AA108.8C8B—C7B—H7BB108.8
C6A—C7A—H7AA108.8C6B—C7B—H7BB108.8
C8A—C7A—H7AB108.8H7BA—C7B—H7BB107.7
C6A—C7A—H7AB108.8C7B—C8B—C3B108.1 (5)
H7AA—C7A—H7AB107.7C7B—C8B—C21B108.6 (5)
C7A—C8A—C21A109.5 (5)C3B—C8B—C21B110.7 (5)
C7A—C8A—C9A111.2 (4)C7B—C8B—C9B110.7 (4)
C21A—C8A—C9A111.4 (4)C3B—C8B—C9B108.4 (4)
C7A—C8A—C3A106.2 (4)C21B—C8B—C9B110.4 (5)
C21A—C8A—C3A110.8 (4)C17B—C9B—C10B111.0 (4)
C9A—C8A—C3A107.6 (5)C17B—C9B—C8B111.7 (4)
C17A—C9A—C10A109.6 (4)C10B—C9B—C8B114.8 (4)
C17A—C9A—C8A113.8 (4)C17B—C9B—H9BA106.2
C10A—C9A—C8A113.5 (5)C10B—C9B—H9BA106.2
C17A—C9A—H9AA106.5C8B—C9B—H9BA106.2
C10A—C9A—H9AA106.5C11B—C10B—C9B113.3 (4)
C8A—C9A—H9AA106.5C11B—C10B—H10C108.9
C9A—C10A—C11A111.5 (6)C9B—C10B—H10C108.9
C9A—C10A—H10A109.3C11B—C10B—H10D108.9
C11A—C10A—H10A109.3C9B—C10B—H10D108.9
C9A—C10A—H10B109.3H10C—C10B—H10D107.7
C11A—C10A—H10B109.3C12B—C11B—C10B112.3 (4)
H10A—C10A—H10B108.0C12B—C11B—H11C109.1
C12A—C11A—C10A113.7 (5)C10B—C11B—H11C109.1
C12A—C11A—H11A108.8C12B—C11B—H11D109.1
C10A—C11A—H11A108.8C10B—C11B—H11D109.1
C12A—C11A—H11B108.8H11C—C11B—H11D107.9
C10A—C11A—H11B108.8C11B—C12B—C16B106.8 (4)
H11A—C11A—H11B107.7C11B—C12B—C22B110.3 (4)
C11A—C12A—C16A106.0 (4)C16B—C12B—C22B111.8 (4)
C11A—C12A—C13A116.3 (5)C11B—C12B—C13B117.9 (4)
C16A—C12A—C13A100.3 (4)C16B—C12B—C13B99.8 (4)
C11A—C12A—C22A110.1 (5)C22B—C12B—C13B109.8 (4)
C16A—C12A—C22A112.4 (4)C24B—C13B—C12B119.7 (4)
C13A—C12A—C22A111.4 (4)C24B—C13B—C14B111.5 (4)
C24A—C13A—C12A121.2 (5)C12B—C13B—C14B103.5 (4)
C24A—C13A—C14A111.8 (5)C24B—C13B—H13B107.2
C12A—C13A—C14A102.7 (4)C12B—C13B—H13B107.2
C24A—C13A—H13A106.8C14B—C13B—H13B107.2
C12A—C13A—H13A106.8C15B—C14B—C13B106.4 (4)
C14A—C13A—H13A106.8C15B—C14B—H14C110.5
C15A—C14A—C13A106.2 (5)C13B—C14B—H14C110.5
C15A—C14A—H14A110.5C15B—C14B—H14D110.5
C13A—C14A—H14A110.5C13B—C14B—H14D110.5
C15A—C14A—H14B110.5H14C—C14B—H14D108.6
C13A—C14A—H14B110.5C16B—C15B—C14B104.2 (4)
H14A—C14A—H14B108.7C16B—C15B—H15C110.9
C16A—C15A—C14A103.4 (5)C14B—C15B—H15C110.9
C16A—C15A—H15A111.1C16B—C15B—H15D110.9
C14A—C15A—H15A111.1C14B—C15B—H15D110.9
C16A—C15A—H15B111.1H15C—C15B—H15D108.9
C14A—C15A—H15B111.1C17B—C16B—C15B118.2 (4)
H15A—C15A—H15B109.0C17B—C16B—C12B114.6 (4)
C15A—C16A—C17A119.7 (4)C15B—C16B—C12B104.8 (4)
C15A—C16A—C12A104.1 (4)C17B—C16B—H16B106.1
C17A—C16A—C12A115.0 (5)C15B—C16B—H16B106.1
C15A—C16A—H16A105.7C12B—C16B—H16B106.1
C17A—C16A—H16A105.7C16B—C17B—C9B109.7 (4)
C12A—C16A—H16A105.7C16B—C17B—C1B110.4 (4)
C9A—C17A—C16A108.2 (4)C9B—C17B—C1B111.5 (4)
C9A—C17A—C1A112.1 (4)C16B—C17B—H17B108.4
C16A—C17A—C1A109.8 (4)C9B—C17B—H17B108.4
C9A—C17A—H17A108.9C1B—C17B—H17B108.4
C16A—C17A—H17A108.9O1B—C18B—N2B122.2 (5)
C1A—C17A—H17A108.9O1B—C18B—C19B121.3 (5)
O1A—C18A—N2A123.3 (5)N2B—C18B—C19B116.5 (5)
O1A—C18A—C19A122.6 (4)C20X—C19B—C18B112.6 (7)
N2A—C18A—C19A114.0 (4)C20B—C19B—C18B120.6 (6)
C20A—C19A—C18A112.4 (4)C20B—C19B—H19C107.2
C20A—C19A—H19A109.1C18B—C19B—H19C107.2
C18A—C19A—H19A109.1C20B—C19B—H19D107.2
C20A—C19A—H19B109.1C18B—C19B—H19D107.2
C18A—C19A—H19B109.1H19C—C19B—H19D106.8
H19A—C19A—H19B107.8C20X—C19B—H19E109.1
N3A—C20A—C19A175.5 (6)C18B—C19B—H19E109.1
C8A—C21A—H21A109.5C20X—C19B—H19F109.1
C8A—C21A—H21B109.5C18B—C19B—H19F109.1
H21A—C21A—H21B109.5H19E—C19B—H19F107.8
C8A—C21A—H21C109.5C8B—C21B—H21D109.5
H21A—C21A—H21C109.5C8B—C21B—H21E109.5
H21B—C21A—H21C109.5H21D—C21B—H21E109.5
C12A—C22A—H22A109.5C8B—C21B—H21F109.5
C12A—C22A—H22B109.5H21D—C21B—H21F109.5
H22A—C22A—H22B109.5H21E—C21B—H21F109.5
C12A—C22A—H22C109.5C12B—C22B—H22D109.5
H22A—C22A—H22C109.5C12B—C22B—H22E109.5
H22B—C22A—H22C109.5H22D—C22B—H22E109.5
C24A—C23A—H23A109.5C12B—C22B—H22F109.5
C24A—C23A—H23B109.5H22D—C22B—H22F109.5
H23A—C23A—H23B109.5H22E—C22B—H22F109.5
C24A—C23A—H23C109.5C24B—C23B—H23D109.5
H23A—C23A—H23C109.5C24B—C23B—H23E109.5
H23B—C23A—H23C109.5H23D—C23B—H23E109.5
C13A—C24A—C25A109.8 (5)C24B—C23B—H23F109.5
C13A—C24A—C23A112.6 (5)H23D—C23B—H23F109.5
C25A—C24A—C23A110.1 (5)H23E—C23B—H23F109.5
C13A—C24A—H24A108.1C23B—C24B—C13B113.1 (5)
C25A—C24A—H24A108.1C23B—C24B—C25B109.4 (4)
C23A—C24A—H24A108.1C13B—C24B—C25B110.5 (4)
C24A—C25A—C26A116.4 (5)C23B—C24B—H24B107.9
C24A—C25A—H25A108.2C13B—C24B—H24B107.9
C26A—C25A—H25A108.2C25B—C24B—H24B107.9
C24A—C25A—H25B108.2C26B—C25B—C24B114.6 (4)
C26A—C25A—H25B108.2C26B—C25B—H25C108.6
H25A—C25A—H25B107.3C24B—C25B—H25C108.6
C27A—C26A—C25A112.1 (5)C26B—C25B—H25D108.6
C27A—C26A—H26A109.2C24B—C25B—H25D108.6
C25A—C26A—H26A109.2H25C—C25B—H25D107.6
C27A—C26A—H26B109.2C27B—C26B—C25B112.3 (4)
C25A—C26A—H26B109.2C27B—C26B—H26C109.1
H26A—C26A—H26B107.9C25B—C26B—H26C109.1
C28A—C27A—C26A115.5 (5)C27B—C26B—H26D109.1
C28A—C27A—H27A108.4C25B—C26B—H26D109.1
C26A—C27A—H27A108.4H26C—C26B—H26D107.9
C28A—C27A—H27B108.4C26B—C27B—C28B114.9 (5)
C26A—C27A—H27B108.4C26B—C27B—H27C108.5
H27A—C27A—H27B107.5C28B—C27B—H27C108.5
C29A—C28A—C27A110.0 (5)C26B—C27B—H27D108.5
C29A—C28A—C30A110.4 (5)C28B—C27B—H27D108.5
C27A—C28A—C30A111.7 (6)H27C—C27B—H27D107.5
C29A—C28A—H28A108.2C30B—C28B—C29B110.3 (5)
C27A—C28A—H28A108.2C30B—C28B—C27B111.0 (5)
C30A—C28A—H28A108.2C29B—C28B—C27B111.9 (4)
C28A—C29A—H29A109.5C30B—C28B—H28B107.8
C28A—C29A—H29B109.5C29B—C28B—H28B107.8
H29A—C29A—H29B109.5C27B—C28B—H28B107.8
C28A—C29A—H29C109.5C28B—C29B—H29D109.5
H29A—C29A—H29C109.5C28B—C29B—H29E109.5
H29B—C29A—H29C109.5H29D—C29B—H29E109.5
C28A—C30A—H30A109.5C28B—C29B—H29F109.5
C28A—C30A—H30B109.5H29D—C29B—H29F109.5
H30A—C30A—H30B109.5H29E—C29B—H29F109.5
C28A—C30A—H30C109.5C28B—C30B—H30D109.5
H30A—C30A—H30C109.5C28B—C30B—H30E109.5
H30B—C30A—H30C109.5H30D—C30B—H30E109.5
C2B—N1B—N2B118.5 (4)C28B—C30B—H30F109.5
C18B—N2B—N1B118.3 (4)H30D—C30B—H30F109.5
C18B—N2B—H1NB111.0H30E—C30B—H30F109.5
N1B—N2B—H1NB129.6
C2A—N1A—N2A—C18A−178.8 (5)N2B—N1B—C2B—C1B−1.2 (9)
N2A—N1A—C2A—C1A0.2 (8)N2B—N1B—C2B—C3B175.3 (5)
N2A—N1A—C2A—C3A−175.8 (4)C17B—C1B—C2B—N1B−135.2 (6)
C17A—C1A—C2A—N1A−118.9 (6)C17B—C1B—C2B—C3B48.2 (7)
C17A—C1A—C2A—C3A57.3 (5)N1B—C2B—C3B—C4B0.6 (8)
N1A—C2A—C3A—C4A−11.8 (6)C1B—C2B—C3B—C4B177.7 (5)
C1A—C2A—C3A—C4A171.5 (4)N1B—C2B—C3B—C8B131.0 (5)
N1A—C2A—C3A—C8A114.1 (5)C1B—C2B—C3B—C8B−51.9 (7)
C1A—C2A—C3A—C8A−62.5 (5)C2B—C3B—C4B—C5B−173.3 (6)
C2A—C3A—C4A—C5A−177.1 (4)C8B—C3B—C4B—C5B57.0 (7)
C8A—C3A—C4A—C5A59.2 (5)C3B—C4B—C5B—C6B−56.1 (7)
C3A—C4A—C5A—C6A−58.9 (6)C3B—C4B—C5B—Cl1B−176.7 (5)
C3A—C4A—C5A—Cl1A179.9 (3)C4B—C5B—C6B—C7B55.3 (7)
C4A—C5A—C6A—C7A57.8 (6)Cl1B—C5B—C6B—C7B175.3 (4)
Cl1A—C5A—C6A—C7A179.0 (4)C5B—C6B—C7B—C8B−54.3 (7)
C5A—C6A—C7A—C8A−58.2 (6)C6B—C7B—C8B—C3B53.3 (6)
C6A—C7A—C8A—C21A−64.5 (6)C6B—C7B—C8B—C21B−66.8 (7)
C6A—C7A—C8A—C9A172.0 (5)C6B—C7B—C8B—C9B171.8 (5)
C6A—C7A—C8A—C3A55.3 (6)C2B—C3B—C8B—C7B174.8 (4)
C2A—C3A—C8A—C7A177.9 (4)C4B—C3B—C8B—C7B−55.7 (6)
C4A—C3A—C8A—C7A−55.5 (6)C2B—C3B—C8B—C21B−66.3 (6)
C2A—C3A—C8A—C21A−63.3 (6)C4B—C3B—C8B—C21B63.1 (6)
C4A—C3A—C8A—C21A63.4 (5)C2B—C3B—C8B—C9B54.9 (6)
C2A—C3A—C8A—C9A58.7 (5)C4B—C3B—C8B—C9B−175.7 (4)
C4A—C3A—C8A—C9A−174.6 (4)C7B—C8B—C9B—C17B−176.1 (5)
C7A—C8A—C9A—C17A−171.9 (5)C3B—C8B—C9B—C17B−57.8 (6)
C21A—C8A—C9A—C17A65.7 (6)C21B—C8B—C9B—C17B63.6 (6)
C3A—C8A—C9A—C17A−56.0 (6)C7B—C8B—C9B—C10B56.3 (6)
C7A—C8A—C9A—C10A61.9 (6)C3B—C8B—C9B—C10B174.6 (4)
C21A—C8A—C9A—C10A−60.5 (6)C21B—C8B—C9B—C10B−63.9 (6)
C3A—C8A—C9A—C10A177.8 (4)C17B—C9B—C10B—C11B50.9 (6)
C17A—C9A—C10A—C11A56.8 (7)C8B—C9B—C10B—C11B178.8 (4)
C8A—C9A—C10A—C11A−174.8 (5)C9B—C10B—C11B—C12B−54.1 (6)
C9A—C10A—C11A—C12A−55.5 (7)C10B—C11B—C12B—C16B55.3 (5)
C10A—C11A—C12A—C16A52.5 (7)C10B—C11B—C12B—C22B−66.3 (6)
C10A—C11A—C12A—C13A162.9 (5)C10B—C11B—C12B—C13B166.5 (4)
C10A—C11A—C12A—C22A−69.2 (6)C11B—C12B—C13B—C24B78.8 (6)
C11A—C12A—C13A—C24A79.9 (7)C16B—C12B—C13B—C24B−166.2 (5)
C16A—C12A—C13A—C24A−166.4 (5)C22B—C12B—C13B—C24B−48.7 (6)
C22A—C12A—C13A—C24A−47.3 (7)C11B—C12B—C13B—C14B−156.4 (4)
C11A—C12A—C13A—C14A−154.5 (5)C16B—C12B—C13B—C14B−41.3 (5)
C16A—C12A—C13A—C14A−40.9 (5)C22B—C12B—C13B—C14B76.2 (5)
C22A—C12A—C13A—C14A78.2 (5)C24B—C13B—C14B—C15B152.8 (4)
C24A—C13A—C14A—C15A151.3 (5)C12B—C13B—C14B—C15B22.8 (5)
C12A—C13A—C14A—C15A19.8 (6)C13B—C14B—C15B—C16B5.2 (6)
C13A—C14A—C15A—C16A9.7 (6)C14B—C15B—C16B—C17B−161.0 (4)
C14A—C15A—C16A—C17A−166.1 (5)C14B—C15B—C16B—C12B−31.9 (5)
C14A—C15A—C16A—C12A−36.0 (6)C11B—C12B—C16B—C17B−59.9 (5)
C11A—C12A—C16A—C15A170.2 (5)C22B—C12B—C16B—C17B60.9 (6)
C13A—C12A—C16A—C15A48.8 (5)C13B—C12B—C16B—C17B176.9 (4)
C22A—C12A—C16A—C15A−69.5 (6)C11B—C12B—C16B—C15B169.0 (4)
C11A—C12A—C16A—C17A−57.0 (6)C22B—C12B—C16B—C15B−70.3 (5)
C13A—C12A—C16A—C17A−178.3 (4)C13B—C12B—C16B—C15B45.8 (5)
C22A—C12A—C16A—C17A63.3 (6)C15B—C16B—C17B—C9B−176.7 (4)
C10A—C9A—C17A—C16A−58.3 (6)C12B—C16B—C17B—C9B58.9 (6)
C8A—C9A—C17A—C16A173.4 (4)C15B—C16B—C17B—C1B−53.5 (6)
C10A—C9A—C17A—C1A−179.5 (5)C12B—C16B—C17B—C1B−177.8 (4)
C8A—C9A—C17A—C1A52.2 (6)C10B—C9B—C17B—C16B−51.9 (5)
C15A—C16A—C17A—C9A−173.2 (5)C8B—C9B—C17B—C16B178.5 (4)
C12A—C16A—C17A—C9A61.7 (5)C10B—C9B—C17B—C1B−174.5 (4)
C15A—C16A—C17A—C1A−50.6 (6)C8B—C9B—C17B—C1B55.9 (6)
C12A—C16A—C17A—C1A−175.7 (4)C2B—C1B—C17B—C16B−172.0 (4)
C2A—C1A—C17A—C9A−50.5 (6)C2B—C1B—C17B—C9B−49.8 (6)
C2A—C1A—C17A—C16A−170.8 (4)N1B—N2B—C18B—O1B179.9 (5)
N1A—N2A—C18A—O1A−178.7 (5)N1B—N2B—C18B—C19B−1.6 (8)
N1A—N2A—C18A—C19A4.2 (7)O1B—C18B—C19B—C20X31.8 (10)
O1A—C18A—C19A—C20A−4.5 (8)N2B—C18B—C19B—C20X−146.7 (7)
N2A—C18A—C19A—C20A172.6 (5)O1B—C18B—C19B—C20B−129.0 (7)
C12A—C13A—C24A—C25A179.5 (5)N2B—C18B—C19B—C20B52.5 (9)
C14A—C13A—C24A—C25A58.2 (6)C12B—C13B—C24B—C23B−52.0 (7)
C12A—C13A—C24A—C23A−57.5 (7)C14B—C13B—C24B—C23B−173.0 (5)
C14A—C13A—C24A—C23A−178.8 (5)C12B—C13B—C24B—C25B−175.0 (5)
C13A—C24A—C25A—C26A−173.5 (5)C14B—C13B—C24B—C25B64.0 (6)
C23A—C24A—C25A—C26A61.9 (7)C23B—C24B—C25B—C26B72.1 (6)
C24A—C25A—C26A—C27A173.2 (6)C13B—C24B—C25B—C26B−162.7 (5)
C25A—C26A—C27A—C28A−178.8 (6)C24B—C25B—C26B—C27B−162.9 (5)
C26A—C27A—C28A—C29A173.3 (6)C25B—C26B—C27B—C28B178.1 (4)
C26A—C27A—C28A—C30A−63.6 (8)C26B—C27B—C28B—C30B−168.9 (5)
C2B—N1B—N2B—C18B177.9 (5)C26B—C27B—C28B—C29B67.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4B—H4BA···N3B0.992.583.469 (10)149
N2A—H1NA···O1Bi0.852.032.870 (6)168
N2B—H1NB···O1Aii0.852.052.894 (6)171
C1A—H1AB···O1Bi0.992.413.362 (7)162
C1B—H1BB···O1Aii0.992.443.352 (6)153
C4A—H4AB···N3Biii0.992.493.476 (9)173
C19A—H19A···N3Biii0.992.573.513 (11)160
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC30H48ClN3O
Mr502.16
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)11.1623 (2), 19.7586 (3), 26.4077 (4)
V (Å3)5824.26 (16)
Z8
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.32 × 0.32 × 0.16
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.951, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		51504, 13243, 12103
Rint0.042
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.104, 0.221, 1.18
No. of reflections13243
No. of parameters655
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.P)2 + 25.2717P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.50, −0.52
Absolute structureFlack (1983), 5882 Friedel pairs
Absolute structure parameter0.05 (11)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4B—H4BA···N3B0.992.583.469 (10)149
N2A—H1NA···O1Bi0.852.032.870 (6)168
N2B—H1NB···O1Aii0.852.052.894 (6)171
C1A—H1AB···O1Bi0.992.413.362 (7)162
C1B—H1BB···O1Aii0.992.443.352 (6)153
C4A—H4AB···N3Biii0.992.493.476 (9)173
C19A—H19A···N3Biii0.992.573.513 (11)160
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2.
 

Footnotes

‡Additional correspondence email: ohasnah@usm.my.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the FRGS grant (203/PKIMIA/6711179), MOSTI grant (No. 09–05-lfn-meb-004) and Research University grant (No.1001/PFIZIK/811151) to conduct this work. SKY also thanks USM for providing Graduate Assistance financial support.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2009). SADABS, APEX2 and SAINT. 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
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 First citationYusufzai, S. K., Osman, H., Sulaiman, O., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o473–o474.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1056-o1057
doi:10.1107/S1600536812009336
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