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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 71| Part 5| May 2015| Pages o343-o344
https://doi.org/10.1107/S2056989015007781

Crystal structure of anagyrine perchlorate

Kambarali K. Turgunov,a* Shukhrat B. Rakhimov,a Valentina I. Vinogradovaa and Bakhodir Tashkhodjaeva

aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
*Correspondence e-mail: kk_turgunov@rambler.ru

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 April 2015; accepted 20 April 2015; online 25 April 2015)

The title mol­ecular salt, C15H21N2O+·ClO4−, crystallizes with four cations (A, B, C and D) and four anions in the chiral unit cell (space group P21). The alkaloid was isolated from the aerial parts of Genista Hispanica collected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid rings C and D. In each cation, ring A is almost planar and ring B adops a sofa conformation with the methyl­ene group bridging to the C ring as the flap. Rings C and D adopt chair conformations with a cis ring junction in all four cations. In the crystal, A+B and C+D dimeric pairs linked by pairs of N—H⋯O hydrogen bonds are observed, which generate R22(16) loops in each case. The dimers are consolidated by weak aromatic π–π stacking inter­actions between the A rings [centroid–centroid distances = 3.913 (3) and 3.915 (3) Å].

CCDC reference: 1060546

Similar articles

1. Related literature

For the isolation of the title alkaloid, see: Orechoff et al. (1934[Orechoff, A., Norkina, S. & Gurewitsch, H. (1934). Berichte, 67, 1394-1398.]); Sagen et al. (2002[Sagen, A.-L., Gertsch, J., Becker, R., Heilmann, J. & Sticher, O. (2002). Phytochemistry, 61, 975-978.]). For NMR spectra of the title alkaloid, see: Sagen et al. (2002[Sagen, A.-L., Gertsch, J., Becker, R., Heilmann, J. & Sticher, O. (2002). Phytochemistry, 61, 975-978.]). For theoretical studies of anagyrine and the crystal structure of anagyrine hydro­chloride monohydrate, see: Galasso et al. (2006[Galasso, V., Przybył, A. K., Christov, V., Kovač, B., Asaro, F. & Zangrando, E. (2006). Chem. Phys. 325, 365-377.]). For a related crystal structure, see: Atta-ur-Rahman et al. (1991[Atta-ur-Rahman Pervin, A., Choudhary, M. I., Hasan, N. & Sener, B. (1991). J. Nat. Prod. 54, 929-935.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H21N2O+·ClO4−

  • Mr = 344.79

  • Monoclinic, P 21

  • a = 7.3550 (3) Å

  • b = 32.982 (1) Å

  • c = 12.8849 (4) Å

  • β = 90.709 (3)°

  • V = 3125.41 (19) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.42 mm−1

  • T = 290 K

  • 0.65 × 0.15 × 0.04 mm

2.2. Data collection

  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.651, Tmax = 1.000

  • 53652 measured reflections

  • 12780 independent reflections

  • 9677 reflections with I > 2σ(I)

  • Rint = 0.105

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.189

  • S = 1.02

  • 12780 reflections

  • 846 parameters

  • 1 restraint

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

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.37 e Å−3

  • Absolute structure: Flack x determined using 3107 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: −0.024 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2AN⋯O1B 1.03 (5) 1.91 (6) 2.741 (6) 136 (5)
N2B—H2CN⋯O1A 0.77 (7) 2.00 (6) 2.742 (5) 163 (6)
N2C—H2EN⋯O1Di 0.90 (9) 2.00 (9) 2.735 (6) 138 (8)
N2D—H2GN⋯O1Cii 1.05 (5) 1.74 (5) 2.754 (5) 159 (5)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1060546

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015007781/hb7409sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007781/hb7409Isup2.hkl

checkCIF report


Comment top

Quinolizidine alkaloids attracted the attention of researchers due to the structural characteristics and pharmacological activity. We have studied the aerial parts of Genista Hispanica collected in Samarkand region and isolated anagyrine with Rf 0.5 (chloro­form-methanol 6:1) along with other alkaloids. Anagyrine a toxic alkaloid found in several species of Lupinus in the western United States. Acute poisoning produces nervousness, depression, loss of muscular control, convulsions, and coma.

Anagyrine perchlorate crystallizes in the monoclinic space group P21 with a long unique b-axis of 32.982 (1) Å .The asymmetric unit consist of four protonated anagyrine molecules and four perchlorate anions. The molecular structure of the alkaloid is shown in Fig. 1. The alkaloid molecule consists of four fused rings - planar ring A fused with the sofa ring B, and a twin-chair C/D fragment where C/D junction is cis. Conformation of all undependent molecules matches. Anagyrine molecule has three asymmetric centers at C6, C8, C10 and in addition by protonation of N2 it becomes as asymmetric senter. Configuration of chiral atoms are C-6R,C-8R,C-10R and N-2S. Crystal structure of thermopsine - a C-10-epimer of anagyrine was investigated by Atta-ur-Rahman et al. (1991).

In the crystal, pairs of hydrogen bonds between protonated N atom of the base and the carbonyl O atom link molecules to form two molecular associates (Fig.2, Table 1.). In addition the associates are linked by weak π–π stacking inter­actions observed between aromatic rings of molecule [centroid—centroid distance = 3.913 (3) Å and 3.915 (3) Å for undependent molecular pairs ]

Experimental top

Synthesis and crystallization top

The powdered air-dried plant material were extracted with 80% ethanol. After distilling off the alcohol, the residue was acidified with H2SO4 and washed with chloro­form, then the extract was basified with 25% aqueous ammonia, the sum of alkaloids (8.81 g) were extracted with chloro­form. The resulting sum were dissolved in ethanol and acidified with HNO3 to a weakly acidic medium, precipitated cytisine nitrate crystals (0.98g) were separated, and the mother liquor was evaporated. The resulting aqueous residue was basified with 25% aqueous ammonia and alkaloids was extracted with chloro­form. The resulting sum of alkaloids was subjected to column chromatography on silica gel eluting with chloro­form-methanol (100: 1) and isolated anagyrine (0.16g). Obtained anagyrine was dissolved in acetone and perchloric acid was added until acidic medium of pH 5-6. Precipitated anagyrine perchlorate crystals were crystallized from methanol with m.p. 315 °C. Colourless prisms were obtained by re-crystallization from water at 50 °C .

Refinement top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 Å (aromatic), 0.97 Å (methylen), 0.98 Å (tertiary carbon) and were refined with Uiso(H)=1.2Ueq(C) for all hydrogen atoms. N-bound H atoms involved in the inter­molecular hydrogen bonding were found by difference Fourier synthesis and refined isotropically [N2A—H = 1.03 (5)Å, N2B—H 0.77 (7) Å, N2C—H 0.90 (9) Å, N2D—H 1.05 (5) Å].

Related literature top

For the isolation of the title alkaloid, see: Orechoff et al. (1934); Sagen et al. (2002). For NMR spectra of the title alkaloid, see: Sagen et al. (2002). For theoretical studies of anagyrine and the crystal structure of anagyrine hydrochloride monohydrate, see: Galasso et al. (2006). For a related crystal structure, see: Atta-ur-Rahman et al. (1991).

Structure description top

Quinolizidine alkaloids attracted the attention of researchers due to the structural characteristics and pharmacological activity. We have studied the aerial parts of Genista Hispanica collected in Samarkand region and isolated anagyrine with Rf 0.5 (chloro­form-methanol 6:1) along with other alkaloids. Anagyrine a toxic alkaloid found in several species of Lupinus in the western United States. Acute poisoning produces nervousness, depression, loss of muscular control, convulsions, and coma.

Anagyrine perchlorate crystallizes in the monoclinic space group P21 with a long unique b-axis of 32.982 (1) Å .The asymmetric unit consist of four protonated anagyrine molecules and four perchlorate anions. The molecular structure of the alkaloid is shown in Fig. 1. The alkaloid molecule consists of four fused rings - planar ring A fused with the sofa ring B, and a twin-chair C/D fragment where C/D junction is cis. Conformation of all undependent molecules matches. Anagyrine molecule has three asymmetric centers at C6, C8, C10 and in addition by protonation of N2 it becomes as asymmetric senter. Configuration of chiral atoms are C-6R,C-8R,C-10R and N-2S. Crystal structure of thermopsine - a C-10-epimer of anagyrine was investigated by Atta-ur-Rahman et al. (1991).

In the crystal, pairs of hydrogen bonds between protonated N atom of the base and the carbonyl O atom link molecules to form two molecular associates (Fig.2, Table 1.). In addition the associates are linked by weak π–π stacking inter­actions observed between aromatic rings of molecule [centroid—centroid distance = 3.913 (3) Å and 3.915 (3) Å for undependent molecular pairs ]

For the isolation of the title alkaloid, see: Orechoff et al. (1934); Sagen et al. (2002). For NMR spectra of the title alkaloid, see: Sagen et al. (2002). For theoretical studies of anagyrine and the crystal structure of anagyrine hydrochloride monohydrate, see: Galasso et al. (2006). For a related crystal structure, see: Atta-ur-Rahman et al. (1991).

Synthesis and crystallization top

The powdered air-dried plant material were extracted with 80% ethanol. After distilling off the alcohol, the residue was acidified with H2SO4 and washed with chloro­form, then the extract was basified with 25% aqueous ammonia, the sum of alkaloids (8.81 g) were extracted with chloro­form. The resulting sum were dissolved in ethanol and acidified with HNO3 to a weakly acidic medium, precipitated cytisine nitrate crystals (0.98g) were separated, and the mother liquor was evaporated. The resulting aqueous residue was basified with 25% aqueous ammonia and alkaloids was extracted with chloro­form. The resulting sum of alkaloids was subjected to column chromatography on silica gel eluting with chloro­form-methanol (100: 1) and isolated anagyrine (0.16g). Obtained anagyrine was dissolved in acetone and perchloric acid was added until acidic medium of pH 5-6. Precipitated anagyrine perchlorate crystals were crystallized from methanol with m.p. 315 °C. Colourless prisms were obtained by re-crystallization from water at 50 °C .

Refinement details top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 Å (aromatic), 0.97 Å (methylen), 0.98 Å (tertiary carbon) and were refined with Uiso(H)=1.2Ueq(C) for all hydrogen atoms. N-bound H atoms involved in the inter­molecular hydrogen bonding were found by difference Fourier synthesis and refined isotropically [N2A—H = 1.03 (5)Å, N2B—H 0.77 (7) Å, N2C—H 0.90 (9) Å, N2D—H 1.05 (5) Å].

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of cation A of the title compound, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding between molecules.
Anagyrine perchlorate top
Crystal data top
C15H21N2O+·ClO4−F(000) = 1456
Mr = 344.79Dx = 1.465 Mg m−3
Monoclinic, P21Melting point: 588(2) K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54184 Å
a = 7.3550 (3) ÅCell parameters from 6414 reflections
b = 32.982 (1) Åθ = 3.7–75.0°
c = 12.8849 (4) ŵ = 2.42 mm−1
β = 90.709 (3)°T = 290 K
V = 3125.41 (19) Å3Prism, colourless
Z = 80.65 × 0.15 × 0.04 mm
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		12780 independent reflections
Radiation source: Enhance (Cu) X-ray Source9677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.105
Detector resolution: 10.2576 pixels mm-1θmax = 77.5°, θmin = 3.4°
ω scansh = −9→8
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −41→41
Tmin = 0.651, Tmax = 1.000l = −16→16
53652 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.064 w = 1/[σ2(Fo2) + (0.0663P)2 + 0.7864P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.189(Δ/σ)max = 0.005
S = 1.02Δρmax = 0.60 e Å−3
12780 reflectionsΔρmin = −0.37 e Å−3
846 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00064 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack x determined using 3107 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: −0.024 (12)
Crystal data top
C15H21N2O+·ClO4−V = 3125.41 (19) Å3
Mr = 344.79Z = 8
Monoclinic, P21Cu Kα radiation
a = 7.3550 (3) ŵ = 2.42 mm−1
b = 32.982 (1) ÅT = 290 K
c = 12.8849 (4) Å0.65 × 0.15 × 0.04 mm
β = 90.709 (3)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		12780 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		9677 reflections with I > 2σ(I)
Tmin = 0.651, Tmax = 1.000Rint = 0.105
53652 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189Δρmax = 0.60 e Å−3
S = 1.02Δρmin = −0.37 e Å−3
12780 reflectionsAbsolute structure: Flack x determined using 3107 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
846 parametersAbsolute structure parameter: −0.024 (12)
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
O1A0.4133 (6)0.31408 (11)0.7883 (3)0.0586 (9)
N1A0.5187 (5)0.35415 (11)0.9204 (3)0.0447 (8)
N2A0.2907 (6)0.38902 (11)1.1098 (3)0.0460 (8)
C1A0.4817 (7)0.34744 (15)0.8144 (4)0.0485 (10)
C2A0.5292 (7)0.37879 (17)0.7450 (4)0.0576 (12)
H2A0.50920.37520.67410.069*
C3A0.6032 (8)0.41377 (17)0.7797 (4)0.0593 (12)
H3A0.63440.43400.73280.071*
C4A0.6333 (8)0.41978 (15)0.8873 (4)0.0569 (12)
H4A0.68030.44430.91110.068*
C5A0.5937 (6)0.38989 (14)0.9558 (4)0.0468 (9)
C6A0.6195 (7)0.39559 (14)1.0709 (4)0.0509 (10)
H6A0.72370.41361.08230.061*
C7A0.6605 (8)0.35544 (16)1.1242 (4)0.0585 (12)
H7A0.68150.35951.19790.070*
H7B0.76780.34301.09480.070*
C8A0.4945 (7)0.32869 (14)1.1059 (4)0.0495 (10)
H8A0.51790.30291.14120.059*
C9A0.4759 (7)0.31962 (13)0.9901 (4)0.0500 (10)
H9A0.55580.29720.97350.060*
H9B0.35220.31090.97570.060*
C10A0.3225 (8)0.34697 (14)1.1534 (4)0.0525 (11)
H10A0.21940.33001.13160.063*
C11A0.3270 (10)0.34759 (18)1.2714 (4)0.0660 (14)
H11A0.43440.36211.29530.079*
H11B0.33450.32001.29730.079*
C12A0.1551 (12)0.3683 (2)1.3153 (5)0.0811 (19)
H12A0.04930.35191.29890.097*
H12B0.16630.37011.39030.097*
C13A0.1284 (10)0.41028 (19)1.2713 (4)0.0677 (14)
H13A0.01510.42151.29620.081*
H13B0.22680.42771.29460.081*
C14A0.1239 (7)0.40890 (16)1.1549 (4)0.0548 (11)
H14A0.11410.43631.12830.066*
H14B0.01670.39411.13210.066*
C15A0.4529 (7)0.41532 (14)1.1185 (3)0.0479 (10)
H15A0.47770.42111.19110.057*
H15B0.42850.44091.08360.057*
O1B0.0848 (6)0.36310 (12)0.9439 (3)0.0591 (9)
N1B0.0180 (6)0.34775 (12)0.7754 (3)0.0464 (8)
N2B0.2143 (5)0.28075 (11)0.6285 (3)0.0428 (8)
C1B0.0737 (7)0.37526 (15)0.8519 (4)0.0498 (10)
C2B0.1114 (8)0.41506 (17)0.8180 (5)0.0633 (13)
H2C0.14670.43450.86640.076*
C3B0.0975 (9)0.42544 (18)0.7174 (5)0.0682 (14)
H3C0.12270.45190.69740.082*
C4B0.0450 (9)0.39665 (17)0.6415 (5)0.0648 (14)
H4C0.03870.40380.57170.078*
C5B0.0042 (8)0.35841 (16)0.6721 (4)0.0538 (11)
C6B−0.0512 (8)0.32671 (17)0.5943 (4)0.0559 (12)
H6C−0.11710.34000.53720.067*
C7B−0.1758 (8)0.2952 (2)0.6424 (4)0.0640 (14)
H7C−0.28460.30810.66860.077*
H7D−0.21170.27520.59100.077*
C8B−0.0701 (7)0.27531 (16)0.7304 (4)0.0546 (11)
H8C−0.15100.25520.76140.066*
C9B−0.0252 (7)0.30642 (15)0.8148 (4)0.0501 (10)
H9C−0.12780.30840.86110.060*
H9D0.07800.29660.85520.060*
C10B0.0950 (7)0.25221 (14)0.6903 (4)0.0495 (10)
H10C0.16570.24270.75050.059*
C11B0.0438 (9)0.21524 (18)0.6244 (5)0.0679 (15)
H11C−0.02040.19590.66730.082*
H11D−0.03840.22370.56910.082*
C12B0.2083 (10)0.19436 (17)0.5769 (5)0.0711 (16)
H12C0.28310.18270.63180.085*
H12D0.16730.17250.53210.085*
C13B0.3193 (9)0.22340 (17)0.5158 (5)0.0653 (14)
H13C0.24850.23320.45700.078*
H13D0.42600.20970.48960.078*
C14B0.3771 (7)0.25872 (16)0.5831 (4)0.0561 (11)
H14C0.44730.27760.54200.067*
H14D0.45460.24890.63910.067*
C15B0.1168 (8)0.30531 (15)0.5495 (3)0.0543 (11)
H15C0.07870.28790.49270.065*
H15D0.19910.32550.52210.065*
O1C0.8812 (5)0.12630 (11)0.2909 (3)0.0560 (8)
N1C0.7799 (5)0.08624 (11)0.4217 (3)0.0433 (7)
N2C1.0207 (6)0.05052 (11)0.6095 (3)0.0456 (8)
C1C0.8095 (6)0.09375 (14)0.3167 (3)0.0453 (9)
C2C0.7495 (7)0.06292 (16)0.2460 (4)0.0514 (10)
H2E0.76590.06660.17520.062*
C3C0.6694 (8)0.02861 (16)0.2800 (4)0.0574 (12)
H3E0.62920.00930.23240.069*
C4C0.6467 (8)0.02195 (15)0.3858 (4)0.0550 (11)
H4E0.5940−0.00200.40850.066*
C5C0.7012 (6)0.05031 (13)0.4561 (4)0.0449 (9)
C6C0.6872 (7)0.04424 (14)0.5715 (4)0.0498 (10)
H6E0.58350.02630.58380.060*
C7C0.6506 (8)0.08412 (16)0.6271 (4)0.0561 (11)
H7E0.54120.09680.59960.067*
H7F0.63540.07950.70090.067*
C8C0.8144 (8)0.11066 (13)0.6082 (4)0.0508 (11)
H8E0.79270.13640.64410.061*
C9C0.8253 (8)0.12038 (13)0.4926 (4)0.0500 (10)
H9E0.74330.14270.47740.060*
H9F0.94760.12950.47780.060*
C10C0.9917 (7)0.09288 (14)0.6542 (4)0.0509 (10)
H10E1.09240.11000.63120.061*
C11C0.9978 (10)0.09176 (17)0.7727 (4)0.0647 (14)
H11E0.99150.11930.79890.078*
H11F0.89200.07730.79730.078*
C12C1.1679 (11)0.0716 (2)0.8160 (5)0.0760 (17)
H12E1.27330.08790.79890.091*
H12F1.16050.07010.89100.091*
C13C1.1914 (10)0.0292 (2)0.7725 (4)0.0715 (15)
H13E1.09370.01190.79620.086*
H13F1.30570.01780.79700.086*
C14C1.1893 (8)0.03078 (18)0.6545 (4)0.0598 (12)
H14E1.29530.04570.63160.072*
H14F1.19830.00340.62770.072*
C15C0.8559 (7)0.02379 (14)0.6161 (3)0.0489 (10)
H15E0.83510.01680.68810.059*
H15F0.8781−0.00120.57850.059*
O1D0.2197 (6)0.07898 (11)0.4471 (3)0.0569 (8)
N1D0.2731 (5)0.09373 (11)0.2775 (3)0.0424 (7)
N2D0.0690 (5)0.16005 (10)0.1287 (3)0.0403 (7)
C1D0.2222 (7)0.06657 (14)0.3553 (3)0.0464 (10)
C2D0.1765 (7)0.02692 (15)0.3226 (4)0.0546 (11)
H2G0.14710.00740.37180.065*
C3D0.1750 (8)0.01683 (15)0.2199 (4)0.0569 (12)
H3G0.1380−0.00900.19960.068*
C4D0.2279 (8)0.04458 (15)0.1455 (4)0.0540 (11)
H4G0.23020.03710.07590.065*
C5D0.2762 (7)0.08259 (14)0.1743 (3)0.0461 (9)
C6D0.3330 (7)0.11426 (15)0.0955 (3)0.0492 (10)
H6G0.39620.10040.03910.059*
C7D0.4602 (7)0.14484 (17)0.1420 (4)0.0554 (12)
H7G0.49570.16440.09000.066*
H7H0.56880.13150.16850.066*
C8D0.3609 (7)0.16602 (14)0.2301 (4)0.0508 (10)
H8G0.44370.18630.25990.061*
C9D0.3199 (7)0.13482 (14)0.3155 (3)0.0480 (10)
H9G0.42540.13280.36110.058*
H9H0.21980.14490.35650.058*
C10D0.1933 (7)0.18822 (13)0.1895 (3)0.0474 (10)
H10G0.12590.19800.24960.057*
C11D0.2425 (9)0.22534 (15)0.1232 (5)0.0623 (14)
H11G0.31190.24430.16560.075*
H11H0.31920.21670.06670.075*
C12D0.0761 (9)0.24698 (16)0.0785 (5)0.0662 (14)
H12G0.00470.25820.13440.079*
H12H0.11440.26920.03440.079*
C13D−0.0384 (9)0.21742 (18)0.0160 (5)0.0664 (14)
H13G0.03060.2077−0.04270.080*
H13H−0.14600.2311−0.01060.080*
C14D−0.0952 (7)0.18134 (16)0.0832 (4)0.0540 (11)
H14G−0.17190.19080.13890.065*
H14H−0.16520.16240.04140.065*
C15D0.1650 (7)0.13525 (14)0.0495 (3)0.0498 (10)
H15G0.20140.1526−0.00730.060*
H15H0.08220.11490.02180.060*
Cl10.5283 (2)0.18310 (5)0.83543 (11)0.0683 (3)
O110.3429 (11)0.1756 (3)0.8283 (6)0.150 (4)
O120.5416 (16)0.2170 (3)0.8995 (9)0.181 (5)
O130.6026 (10)0.1909 (2)0.7395 (5)0.120 (2)
O140.6176 (15)0.1521 (3)0.8875 (7)0.161 (4)
Cl20.6107 (3)0.42676 (4)0.45172 (10)0.0705 (4)
O210.452 (2)0.4201 (8)0.4894 (10)0.355 (15)
O220.590 (2)0.4423 (4)0.3594 (7)0.244 (8)
O230.670 (2)0.3903 (3)0.4433 (15)0.298 (11)
O240.7186 (14)0.4502 (2)0.5180 (6)0.153 (4)
Cl30.7597 (2)0.25649 (4)0.33650 (10)0.0654 (3)
O310.6728 (15)0.2873 (3)0.3883 (7)0.167 (4)
O320.7512 (19)0.2224 (3)0.3989 (9)0.195 (5)
O330.6803 (8)0.24878 (19)0.2401 (4)0.1007 (18)
O340.9439 (11)0.2649 (4)0.3267 (6)0.182 (5)
Cl40.7284 (3)0.02077 (4)0.96609 (10)0.0700 (4)
O410.8759 (18)−0.0026 (3)1.0007 (9)0.196 (6)
O420.5883 (17)0.0062 (4)1.0232 (7)0.198 (6)
O430.7115 (10)0.01230 (17)0.8606 (3)0.0973 (18)
O440.7781 (14)0.06101 (17)0.9878 (4)0.135 (3)
H2AN0.259 (8)0.3892 (17)1.032 (4)0.051 (14)*
H2CN0.264 (9)0.2945 (18)0.668 (5)0.052 (15)*
H2EN1.034 (13)0.055 (3)0.541 (7)0.11 (3)*
H2GN0.015 (7)0.1414 (16)0.187 (4)0.043 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.060 (2)0.0617 (19)0.0538 (19)−0.0031 (16)−0.0063 (16)−0.0159 (15)
N1A0.040 (2)0.0453 (17)0.0491 (19)−0.0026 (15)0.0007 (15)−0.0076 (14)
N2A0.050 (2)0.0452 (17)0.0423 (18)−0.0046 (16)−0.0050 (16)0.0012 (14)
C1A0.038 (2)0.055 (2)0.053 (2)0.0049 (19)−0.0001 (18)−0.0126 (19)
C2A0.048 (3)0.074 (3)0.051 (3)0.010 (2)0.007 (2)−0.002 (2)
C3A0.058 (3)0.062 (3)0.059 (3)0.001 (2)0.015 (2)0.006 (2)
C4A0.058 (3)0.055 (3)0.058 (3)−0.010 (2)0.013 (2)−0.002 (2)
C5A0.040 (2)0.045 (2)0.055 (2)−0.0056 (18)0.0040 (18)−0.0063 (18)
C6A0.045 (3)0.052 (2)0.056 (3)−0.0108 (19)−0.0066 (19)−0.0060 (19)
C7A0.053 (3)0.062 (3)0.061 (3)0.003 (2)−0.017 (2)−0.001 (2)
C8A0.051 (3)0.045 (2)0.053 (2)−0.0014 (18)−0.008 (2)0.0045 (17)
C9A0.054 (3)0.044 (2)0.052 (2)0.0011 (19)−0.002 (2)−0.0052 (17)
C10A0.061 (3)0.046 (2)0.051 (2)−0.014 (2)−0.008 (2)0.0050 (18)
C11A0.090 (4)0.062 (3)0.045 (3)−0.007 (3)−0.003 (3)0.014 (2)
C12A0.107 (6)0.081 (4)0.055 (3)−0.011 (4)0.023 (3)0.011 (3)
C13A0.076 (4)0.071 (3)0.057 (3)0.003 (3)0.016 (3)−0.007 (2)
C14A0.054 (3)0.059 (3)0.051 (2)−0.003 (2)0.006 (2)−0.001 (2)
C15A0.051 (3)0.047 (2)0.045 (2)−0.0101 (19)−0.0018 (18)−0.0063 (16)
O1B0.061 (2)0.070 (2)0.0461 (18)0.0027 (17)−0.0119 (15)−0.0126 (15)
N1B0.044 (2)0.0549 (19)0.0403 (18)0.0049 (16)−0.0033 (15)−0.0072 (15)
N2B0.045 (2)0.0442 (17)0.0396 (17)−0.0071 (15)−0.0041 (15)−0.0049 (14)
C1B0.039 (2)0.060 (2)0.050 (2)0.0102 (19)−0.0046 (18)−0.0109 (19)
C2B0.053 (3)0.055 (3)0.081 (4)0.003 (2)−0.001 (3)−0.018 (2)
C3B0.060 (4)0.056 (3)0.088 (4)0.005 (2)0.011 (3)0.009 (3)
C4B0.072 (4)0.064 (3)0.058 (3)0.020 (3)0.001 (3)0.007 (2)
C5B0.056 (3)0.063 (3)0.042 (2)0.011 (2)−0.002 (2)0.0016 (19)
C6B0.056 (3)0.071 (3)0.041 (2)0.013 (2)−0.013 (2)−0.005 (2)
C7B0.039 (3)0.090 (4)0.063 (3)−0.001 (2)−0.001 (2)−0.027 (3)
C8B0.052 (3)0.062 (3)0.051 (2)−0.018 (2)0.007 (2)−0.010 (2)
C9B0.050 (3)0.060 (3)0.040 (2)−0.006 (2)0.0037 (18)−0.0037 (18)
C10B0.053 (3)0.047 (2)0.049 (2)−0.0091 (19)0.0043 (19)−0.0035 (17)
C11B0.067 (4)0.062 (3)0.076 (4)−0.025 (3)0.008 (3)−0.015 (3)
C12B0.083 (4)0.055 (3)0.075 (4)−0.005 (3)−0.004 (3)−0.026 (3)
C13B0.061 (3)0.062 (3)0.073 (3)−0.001 (2)0.003 (3)−0.025 (3)
C14B0.050 (3)0.057 (3)0.062 (3)0.006 (2)−0.003 (2)−0.013 (2)
C15B0.067 (3)0.061 (3)0.035 (2)0.001 (2)0.002 (2)0.0004 (18)
O1C0.057 (2)0.0607 (19)0.0500 (17)−0.0013 (16)0.0074 (15)0.0148 (14)
N1C0.043 (2)0.0449 (17)0.0420 (18)−0.0007 (15)0.0033 (14)0.0020 (14)
N2C0.053 (2)0.0494 (19)0.0346 (17)−0.0036 (16)0.0057 (15)0.0040 (14)
C1C0.041 (2)0.054 (2)0.041 (2)0.0054 (19)−0.0002 (17)0.0071 (17)
C2C0.046 (3)0.067 (3)0.041 (2)0.007 (2)−0.0032 (18)−0.0056 (19)
C3C0.056 (3)0.059 (3)0.056 (3)0.009 (2)−0.010 (2)−0.014 (2)
C4C0.057 (3)0.048 (2)0.061 (3)−0.007 (2)0.000 (2)−0.007 (2)
C5C0.036 (2)0.050 (2)0.049 (2)−0.0040 (17)0.0008 (17)0.0022 (17)
C6C0.051 (3)0.048 (2)0.050 (2)−0.0107 (19)0.013 (2)0.0030 (18)
C7C0.054 (3)0.063 (3)0.052 (3)−0.004 (2)0.014 (2)0.001 (2)
C8C0.061 (3)0.042 (2)0.050 (2)−0.0019 (19)0.011 (2)−0.0077 (17)
C9C0.059 (3)0.045 (2)0.047 (2)−0.0036 (19)−0.001 (2)0.0022 (17)
C10C0.060 (3)0.050 (2)0.043 (2)−0.011 (2)0.0060 (19)0.0022 (17)
C11C0.092 (4)0.061 (3)0.042 (2)−0.005 (3)0.003 (2)−0.007 (2)
C12C0.089 (5)0.088 (4)0.050 (3)−0.013 (4)−0.013 (3)−0.002 (3)
C13C0.077 (4)0.087 (4)0.050 (3)0.004 (3)−0.004 (3)0.011 (3)
C14C0.057 (3)0.068 (3)0.055 (3)0.009 (2)0.004 (2)0.011 (2)
C15C0.057 (3)0.046 (2)0.044 (2)−0.004 (2)0.0043 (19)0.0037 (17)
O1D0.066 (2)0.0650 (19)0.0397 (16)0.0003 (17)0.0116 (15)0.0094 (14)
N1D0.042 (2)0.0485 (17)0.0369 (16)0.0005 (15)0.0040 (14)0.0026 (13)
N2D0.0384 (19)0.0408 (16)0.0419 (17)−0.0041 (14)0.0030 (14)0.0061 (13)
C1D0.046 (3)0.053 (2)0.041 (2)0.0062 (19)0.0088 (17)0.0103 (17)
C2D0.051 (3)0.051 (2)0.061 (3)0.004 (2)0.005 (2)0.011 (2)
C3D0.062 (3)0.044 (2)0.065 (3)0.006 (2)0.007 (2)0.000 (2)
C4D0.060 (3)0.056 (2)0.045 (2)0.010 (2)0.003 (2)−0.0046 (19)
C5D0.045 (2)0.055 (2)0.038 (2)0.0077 (19)0.0029 (17)0.0017 (17)
C6D0.051 (3)0.060 (2)0.0372 (19)0.002 (2)0.0140 (18)0.0031 (17)
C7D0.031 (2)0.075 (3)0.059 (3)−0.007 (2)0.0002 (19)0.028 (2)
C8D0.047 (3)0.053 (2)0.051 (2)−0.0144 (19)−0.0042 (19)0.0082 (19)
C9D0.049 (3)0.058 (2)0.037 (2)−0.006 (2)−0.0053 (17)0.0024 (17)
C10D0.057 (3)0.042 (2)0.043 (2)−0.0100 (19)0.0025 (18)0.0010 (16)
C11D0.073 (4)0.049 (2)0.065 (3)−0.018 (2)−0.008 (3)0.014 (2)
C12D0.080 (4)0.047 (2)0.071 (3)−0.008 (2)0.004 (3)0.016 (2)
C13D0.067 (4)0.068 (3)0.065 (3)−0.002 (3)−0.006 (3)0.025 (3)
C14D0.047 (3)0.056 (2)0.059 (3)−0.001 (2)0.002 (2)0.018 (2)
C15D0.059 (3)0.056 (2)0.0351 (19)0.004 (2)0.0044 (18)0.0027 (17)
Cl10.0701 (9)0.0747 (8)0.0602 (7)−0.0005 (7)0.0010 (6)0.0107 (6)
O110.099 (5)0.237 (10)0.114 (5)−0.075 (6)0.002 (4)0.053 (6)
O120.197 (11)0.136 (7)0.211 (10)0.006 (7)0.029 (8)−0.090 (7)
O130.106 (5)0.149 (6)0.105 (4)0.017 (4)0.039 (4)0.050 (4)
O140.202 (10)0.155 (7)0.124 (6)0.066 (7)−0.028 (6)0.041 (5)
Cl20.1003 (12)0.0585 (6)0.0522 (6)0.0064 (7)−0.0139 (7)−0.0059 (5)
O210.232 (16)0.68 (4)0.151 (10)−0.22 (2)0.081 (10)−0.093 (17)
O220.350 (16)0.269 (13)0.110 (6)−0.210 (13)−0.120 (8)0.074 (7)
O230.331 (19)0.117 (7)0.44 (2)0.107 (10)−0.243 (18)−0.132 (10)
O240.243 (10)0.091 (4)0.121 (5)−0.004 (5)−0.107 (6)−0.023 (4)
Cl30.0663 (8)0.0713 (7)0.0584 (7)0.0034 (6)−0.0049 (6)−0.0103 (5)
O310.206 (10)0.174 (8)0.122 (6)0.079 (7)−0.004 (6)−0.070 (6)
O320.274 (15)0.119 (6)0.192 (10)0.028 (8)−0.049 (9)0.059 (6)
O330.092 (4)0.119 (4)0.090 (3)0.020 (3)−0.037 (3)−0.027 (3)
O340.088 (5)0.338 (15)0.119 (5)−0.068 (7)0.002 (4)−0.092 (7)
Cl40.1067 (12)0.0591 (6)0.0445 (6)−0.0147 (7)0.0163 (6)−0.0037 (5)
O410.260 (14)0.134 (7)0.192 (10)0.046 (8)−0.121 (10)−0.031 (7)
O420.242 (12)0.241 (11)0.113 (5)−0.130 (10)0.107 (7)−0.060 (6)
O430.148 (5)0.097 (3)0.047 (2)−0.033 (3)0.012 (3)−0.003 (2)
O440.268 (11)0.069 (3)0.068 (3)−0.033 (4)0.011 (4)−0.012 (2)
Geometric parameters (Å, º) top
O1A—C1A1.254 (6)C1C—C2C1.432 (7)
N1A—C5A1.377 (6)C2C—C3C1.351 (8)
N1A—C1A1.407 (6)C2C—H2E0.9300
N1A—C9A1.487 (6)C3C—C4C1.393 (8)
N2A—C15A1.478 (6)C3C—H3E0.9300
N2A—C14A1.513 (7)C4C—C5C1.359 (7)
N2A—C10A1.514 (6)C4C—H4E0.9300
N2A—H2AN1.03 (6)C5C—C6C1.504 (6)
C1A—C2A1.414 (8)C6C—C15C1.520 (7)
C2A—C3A1.349 (8)C6C—C7C1.524 (7)
C2A—H2A0.9300C6C—H6E0.9800
C3A—C4A1.414 (8)C7C—C8C1.512 (7)
C3A—H3A0.9300C7C—H7E0.9700
C4A—C5A1.357 (7)C7C—H7F0.9700
C4A—H4A0.9300C8C—C9C1.526 (6)
C5A—C6A1.505 (7)C8C—C10C1.541 (8)
C6A—C7A1.520 (7)C8C—H8E0.9800
C6A—C15A1.523 (7)C9C—H9E0.9700
C6A—H6A0.9800C9C—H9F0.9700
C7A—C8A1.522 (7)C10C—C11C1.527 (6)
C7A—H7A0.9700C10C—H10E0.9800
C7A—H7B0.9700C11C—C12C1.518 (10)
C8A—C9A1.526 (7)C11C—H11E0.9700
C8A—C10A1.536 (8)C11C—H11F0.9700
C8A—H8A0.9800C12C—C13C1.517 (10)
C9A—H9A0.9700C12C—H12E0.9700
C9A—H9B0.9700C12C—H12F0.9700
C10A—C11A1.521 (7)C13C—C14C1.521 (7)
C10A—H10A0.9800C13C—H13E0.9700
C11A—C12A1.550 (10)C13C—H13F0.9700
C11A—H11A0.9700C14C—H14E0.9700
C11A—H11B0.9700C14C—H14F0.9700
C12A—C13A1.507 (9)C15C—H15E0.9700
C12A—H12A0.9700C15C—H15F0.9700
C12A—H12B0.9700O1D—C1D1.252 (6)
C13A—C14A1.500 (7)N1D—C5D1.380 (6)
C13A—H13A0.9700N1D—C1D1.399 (5)
C13A—H13B0.9700N1D—C9D1.480 (6)
C14A—H14A0.9700N2D—C15D1.492 (6)
C14A—H14B0.9700N2D—C14D1.509 (6)
C15A—H15A0.9700N2D—C10D1.515 (6)
C15A—H15B0.9700N2D—H2GN1.05 (5)
O1B—C1B1.253 (6)C1D—C2D1.413 (7)
N1B—C5B1.379 (6)C2D—C3D1.365 (8)
N1B—C1B1.397 (6)C2D—H2G0.9300
N1B—C9B1.490 (6)C3D—C4D1.384 (7)
N2B—C15B1.479 (6)C3D—H3G0.9300
N2B—C10B1.519 (6)C4D—C5D1.353 (7)
N2B—C14B1.524 (6)C4D—H4G0.9300
N2B—H2CN0.77 (6)C5D—C6D1.519 (6)
C1B—C2B1.412 (8)C6D—C7D1.496 (7)
C2B—C3B1.343 (9)C6D—C15D1.529 (7)
C2B—H2C0.9300C6D—H6G0.9800
C3B—C4B1.414 (9)C7D—C8D1.526 (8)
C3B—H3C0.9300C7D—H7G0.9700
C4B—C5B1.356 (8)C7D—H7H0.9700
C4B—H4C0.9300C8D—C10D1.521 (7)
C5B—C6B1.502 (7)C8D—C9D1.539 (6)
C6B—C7B1.522 (9)C8D—H8G0.9800
C6B—C15B1.541 (8)C9D—H9G0.9700
C6B—H6C0.9800C9D—H9H0.9700
C7B—C8B1.516 (8)C10D—C11D1.538 (6)
C7B—H7C0.9700C10D—H10G0.9800
C7B—H7D0.9700C11D—C12D1.524 (9)
C8B—C10B1.528 (8)C11D—H11G0.9700
C8B—C9B1.529 (6)C11D—H11H0.9700
C8B—H8C0.9800C12D—C13D1.514 (9)
C9B—H9C0.9700C12D—H12G0.9700
C9B—H9D0.9700C12D—H12H0.9700
C10B—C11B1.530 (6)C13D—C14D1.533 (7)
C10B—H10C0.9800C13D—H13G0.9700
C11B—C12B1.527 (9)C13D—H13H0.9700
C11B—H11C0.9700C14D—H14G0.9700
C11B—H11D0.9700C14D—H14H0.9700
C12B—C13B1.490 (9)C15D—H15G0.9700
C12B—H12C0.9700C15D—H15H0.9700
C12B—H12D0.9700Cl1—O131.381 (6)
C13B—C14B1.510 (7)Cl1—O141.385 (7)
C13B—H13C0.9700Cl1—O111.387 (7)
C13B—H13D0.9700Cl1—O121.393 (8)
C14B—H14C0.9700Cl2—O231.285 (8)
C14B—H14D0.9700Cl2—O211.290 (13)
C15B—H15C0.9700Cl2—O221.302 (8)
C15B—H15D0.9700Cl2—O241.392 (6)
O1C—C1C1.243 (6)Cl3—O311.377 (7)
N1C—C5C1.394 (6)Cl3—O321.385 (9)
N1C—C1C1.395 (6)Cl3—O331.389 (5)
N1C—C9C1.486 (6)Cl3—O341.390 (8)
N2C—C15C1.502 (6)Cl4—O421.362 (8)
N2C—C14C1.510 (7)Cl4—O431.391 (5)
N2C—C10C1.527 (6)Cl4—O411.400 (10)
N2C—H2EN0.91 (9)Cl4—O441.404 (5)
C5A—N1A—C1A121.9 (4)C3C—C2C—C1C121.4 (4)
C5A—N1A—C9A122.9 (4)C3C—C2C—H2E119.3
C1A—N1A—C9A115.2 (4)C1C—C2C—H2E119.3
C15A—N2A—C14A112.0 (4)C2C—C3C—C4C120.5 (5)
C15A—N2A—C10A112.9 (4)C2C—C3C—H3E119.8
C14A—N2A—C10A112.1 (4)C4C—C3C—H3E119.8
C15A—N2A—H2AN104 (3)C5C—C4C—C3C120.4 (5)
C14A—N2A—H2AN101 (3)C5C—C4C—H4E119.8
C10A—N2A—H2AN114 (3)C3C—C4C—H4E119.8
O1A—C1A—N1A118.1 (5)C4C—C5C—N1C119.5 (4)
O1A—C1A—C2A125.0 (5)C4C—C5C—C6C122.9 (4)
N1A—C1A—C2A116.9 (4)N1C—C5C—C6C117.5 (4)
C3A—C2A—C1A121.1 (5)C5C—C6C—C15C111.5 (4)
C3A—C2A—H2A119.4C5C—C6C—C7C111.4 (4)
C1A—C2A—H2A119.4C15C—C6C—C7C110.7 (4)
C2A—C3A—C4A120.2 (5)C5C—C6C—H6E107.7
C2A—C3A—H3A119.9C15C—C6C—H6E107.7
C4A—C3A—H3A119.9C7C—C6C—H6E107.7
C5A—C4A—C3A120.2 (5)C8C—C7C—C6C106.1 (4)
C5A—C4A—H4A119.9C8C—C7C—H7E110.5
C3A—C4A—H4A119.9C6C—C7C—H7E110.5
C4A—C5A—N1A119.6 (4)C8C—C7C—H7F110.5
C4A—C5A—C6A121.7 (4)C6C—C7C—H7F110.5
N1A—C5A—C6A118.6 (4)H7E—C7C—H7F108.7
C5A—C6A—C7A111.0 (4)C7C—C8C—C9C109.3 (4)
C5A—C6A—C15A111.0 (4)C7C—C8C—C10C112.9 (4)
C7A—C6A—C15A110.3 (4)C9C—C8C—C10C113.6 (4)
C5A—C6A—H6A108.2C7C—C8C—H8E106.8
C7A—C6A—H6A108.2C9C—C8C—H8E106.8
C15A—C6A—H6A108.2C10C—C8C—H8E106.8
C6A—C7A—C8A106.3 (4)N1C—C9C—C8C115.3 (4)
C6A—C7A—H7A110.5N1C—C9C—H9E108.5
C8A—C7A—H7A110.5C8C—C9C—H9E108.5
C6A—C7A—H7B110.5N1C—C9C—H9F108.5
C8A—C7A—H7B110.5C8C—C9C—H9F108.5
H7A—C7A—H7B108.7H9E—C9C—H9F107.5
C7A—C8A—C9A109.1 (4)N2C—C10C—C11C110.6 (4)
C7A—C8A—C10A111.9 (4)N2C—C10C—C8C108.9 (4)
C9A—C8A—C10A113.7 (4)C11C—C10C—C8C114.1 (5)
C7A—C8A—H8A107.3N2C—C10C—H10E107.7
C9A—C8A—H8A107.3C11C—C10C—H10E107.7
C10A—C8A—H8A107.3C8C—C10C—H10E107.7
N1A—C9A—C8A115.0 (4)C12C—C11C—C10C113.1 (5)
N1A—C9A—H9A108.5C12C—C11C—H11E109.0
C8A—C9A—H9A108.5C10C—C11C—H11E109.0
N1A—C9A—H9B108.5C12C—C11C—H11F109.0
C8A—C9A—H9B108.5C10C—C11C—H11F109.0
H9A—C9A—H9B107.5H11E—C11C—H11F107.8
N2A—C10A—C11A111.1 (4)C13C—C12C—C11C111.4 (5)
N2A—C10A—C8A109.6 (4)C13C—C12C—H12E109.3
C11A—C10A—C8A113.4 (5)C11C—C12C—H12E109.3
N2A—C10A—H10A107.5C13C—C12C—H12F109.3
C11A—C10A—H10A107.5C11C—C12C—H12F109.3
C8A—C10A—H10A107.5H12E—C12C—H12F108.0
C10A—C11A—C12A111.3 (5)C12C—C13C—C14C109.7 (5)
C10A—C11A—H11A109.4C12C—C13C—H13E109.7
C12A—C11A—H11A109.4C14C—C13C—H13E109.7
C10A—C11A—H11B109.4C12C—C13C—H13F109.7
C12A—C11A—H11B109.4C14C—C13C—H13F109.7
H11A—C11A—H11B108.0H13E—C13C—H13F108.2
C13A—C12A—C11A111.8 (5)N2C—C14C—C13C113.3 (5)
C13A—C12A—H12A109.3N2C—C14C—H14E108.9
C11A—C12A—H12A109.3C13C—C14C—H14E108.9
C13A—C12A—H12B109.3N2C—C14C—H14F108.9
C11A—C12A—H12B109.3C13C—C14C—H14F108.9
H12A—C12A—H12B107.9H14E—C14C—H14F107.7
C14A—C13A—C12A110.5 (5)N2C—C15C—C6C112.0 (4)
C14A—C13A—H13A109.6N2C—C15C—H15E109.2
C12A—C13A—H13A109.6C6C—C15C—H15E109.2
C14A—C13A—H13B109.6N2C—C15C—H15F109.2
C12A—C13A—H13B109.6C6C—C15C—H15F109.2
H13A—C13A—H13B108.1H15E—C15C—H15F107.9
C13A—C14A—N2A112.9 (5)C5D—N1D—C1D121.8 (4)
C13A—C14A—H14A109.0C5D—N1D—C9D123.8 (4)
N2A—C14A—H14A109.0C1D—N1D—C9D114.4 (4)
C13A—C14A—H14B109.0C15D—N2D—C14D111.9 (4)
N2A—C14A—H14B109.0C15D—N2D—C10D113.7 (4)
H14A—C14A—H14B107.8C14D—N2D—C10D113.0 (4)
N2A—C15A—C6A111.8 (4)C15D—N2D—H2GN111 (3)
N2A—C15A—H15A109.3C14D—N2D—H2GN104 (3)
C6A—C15A—H15A109.3C10D—N2D—H2GN103 (3)
N2A—C15A—H15B109.3O1D—C1D—N1D118.4 (4)
C6A—C15A—H15B109.3O1D—C1D—C2D125.3 (4)
H15A—C15A—H15B107.9N1D—C1D—C2D116.4 (4)
C5B—N1B—C1B122.2 (4)C3D—C2D—C1D120.9 (5)
C5B—N1B—C9B123.3 (4)C3D—C2D—H2G119.6
C1B—N1B—C9B114.6 (4)C1D—C2D—H2G119.6
C15B—N2B—C10B114.9 (4)C2D—C3D—C4D120.7 (5)
C15B—N2B—C14B111.9 (4)C2D—C3D—H3G119.6
C10B—N2B—C14B111.6 (4)C4D—C3D—H3G119.6
C15B—N2B—H2CN111 (4)C5D—C4D—C3D119.9 (5)
C10B—N2B—H2CN107 (4)C5D—C4D—H4G120.1
C14B—N2B—H2CN100 (5)C3D—C4D—H4G120.1
O1B—C1B—N1B118.3 (5)C4D—C5D—N1D120.2 (4)
O1B—C1B—C2B125.4 (5)C4D—C5D—C6D121.8 (4)
N1B—C1B—C2B116.3 (5)N1D—C5D—C6D118.0 (4)
C3B—C2B—C1B121.5 (5)C7D—C6D—C5D111.8 (4)
C3B—C2B—H2C119.3C7D—C6D—C15D110.4 (4)
C1B—C2B—H2C119.3C5D—C6D—C15D110.0 (4)
C2B—C3B—C4B120.9 (6)C7D—C6D—H6G108.2
C2B—C3B—H3C119.6C5D—C6D—H6G108.2
C4B—C3B—H3C119.6C15D—C6D—H6G108.2
C5B—C4B—C3B118.8 (5)C6D—C7D—C8D107.7 (4)
C5B—C4B—H4C120.6C6D—C7D—H7G110.2
C3B—C4B—H4C120.6C8D—C7D—H7G110.2
C4B—C5B—N1B120.3 (5)C6D—C7D—H7H110.2
C4B—C5B—C6B120.8 (5)C8D—C7D—H7H110.2
N1B—C5B—C6B118.9 (5)H7G—C7D—H7H108.5
C5B—C6B—C7B111.2 (4)C10D—C8D—C7D111.0 (4)
C5B—C6B—C15B110.9 (4)C10D—C8D—C9D113.8 (4)
C7B—C6B—C15B109.3 (5)C7D—C8D—C9D109.0 (4)
C5B—C6B—H6C108.5C10D—C8D—H8G107.6
C7B—C6B—H6C108.5C7D—C8D—H8G107.6
C15B—C6B—H6C108.5C9D—C8D—H8G107.6
C8B—C7B—C6B107.1 (4)N1D—C9D—C8D115.0 (4)
C8B—C7B—H7C110.3N1D—C9D—H9G108.5
C6B—C7B—H7C110.3C8D—C9D—H9G108.5
C8B—C7B—H7D110.3N1D—C9D—H9H108.5
C6B—C7B—H7D110.3C8D—C9D—H9H108.5
H7C—C7B—H7D108.5H9G—C9D—H9H107.5
C7B—C8B—C10B111.5 (4)N2D—C10D—C8D111.3 (4)
C7B—C8B—C9B110.2 (4)N2D—C10D—C11D110.2 (4)
C10B—C8B—C9B114.2 (4)C8D—C10D—C11D112.3 (4)
C7B—C8B—H8C106.9N2D—C10D—H10G107.6
C10B—C8B—H8C106.9C8D—C10D—H10G107.6
C9B—C8B—H8C106.9C11D—C10D—H10G107.6
N1B—C9B—C8B114.6 (4)C12D—C11D—C10D112.9 (5)
N1B—C9B—H9C108.6C12D—C11D—H11G109.0
C8B—C9B—H9C108.6C10D—C11D—H11G109.0
N1B—C9B—H9D108.6C12D—C11D—H11H109.0
C8B—C9B—H9D108.6C10D—C11D—H11H109.0
H9C—C9B—H9D107.6H11G—C11D—H11H107.8
N2B—C10B—C8B109.5 (4)C13D—C12D—C11D109.8 (5)
N2B—C10B—C11B110.0 (4)C13D—C12D—H12G109.7
C8B—C10B—C11B113.2 (4)C11D—C12D—H12G109.7
N2B—C10B—H10C108.0C13D—C12D—H12H109.7
C8B—C10B—H10C108.0C11D—C12D—H12H109.7
C11B—C10B—H10C108.0H12G—C12D—H12H108.2
C12B—C11B—C10B113.0 (5)C12D—C13D—C14D110.7 (5)
C12B—C11B—H11C109.0C12D—C13D—H13G109.5
C10B—C11B—H11C109.0C14D—C13D—H13G109.5
C12B—C11B—H11D109.0C12D—C13D—H13H109.5
C10B—C11B—H11D109.0C14D—C13D—H13H109.5
H11C—C11B—H11D107.8H13G—C13D—H13H108.1
C13B—C12B—C11B111.3 (5)N2D—C14D—C13D111.0 (4)
C13B—C12B—H12C109.4N2D—C14D—H14G109.4
C11B—C12B—H12C109.4C13D—C14D—H14G109.4
C13B—C12B—H12D109.4N2D—C14D—H14H109.4
C11B—C12B—H12D109.4C13D—C14D—H14H109.4
H12C—C12B—H12D108.0H14G—C14D—H14H108.0
C12B—C13B—C14B110.2 (5)N2D—C15D—C6D111.7 (4)
C12B—C13B—H13C109.6N2D—C15D—H15G109.3
C14B—C13B—H13C109.6C6D—C15D—H15G109.3
C12B—C13B—H13D109.6N2D—C15D—H15H109.3
C14B—C13B—H13D109.6C6D—C15D—H15H109.3
H13C—C13B—H13D108.1H15G—C15D—H15H107.9
C13B—C14B—N2B111.8 (4)O13—Cl1—O14112.3 (5)
C13B—C14B—H14C109.3O13—Cl1—O11112.0 (5)
N2B—C14B—H14C109.3O14—Cl1—O11111.1 (6)
C13B—C14B—H14D109.3O13—Cl1—O12110.8 (6)
N2B—C14B—H14D109.3O14—Cl1—O12106.1 (7)
H14C—C14B—H14D107.9O11—Cl1—O12104.1 (7)
N2B—C15B—C6B112.2 (4)O23—Cl2—O21100.5 (13)
N2B—C15B—H15C109.2O23—Cl2—O22109.0 (11)
C6B—C15B—H15C109.2O21—Cl2—O22108.4 (11)
N2B—C15B—H15D109.2O23—Cl2—O24112.3 (6)
C6B—C15B—H15D109.2O21—Cl2—O24112.1 (8)
H15C—C15B—H15D107.9O22—Cl2—O24113.6 (5)
C5C—N1C—C1C122.0 (4)O31—Cl3—O32107.0 (7)
C5C—N1C—C9C122.7 (4)O31—Cl3—O33112.1 (5)
C1C—N1C—C9C115.2 (4)O32—Cl3—O33110.5 (6)
C15C—N2C—C14C112.6 (4)O31—Cl3—O34110.8 (7)
C15C—N2C—C10C113.5 (4)O32—Cl3—O34105.4 (8)
C14C—N2C—C10C111.6 (4)O33—Cl3—O34110.8 (4)
C15C—N2C—H2EN105 (6)O42—Cl4—O43113.4 (5)
C14C—N2C—H2EN111 (6)O42—Cl4—O41102.8 (8)
C10C—N2C—H2EN103 (6)O43—Cl4—O41105.1 (6)
O1C—C1C—N1C119.0 (4)O42—Cl4—O44115.1 (6)
O1C—C1C—C2C124.9 (4)O43—Cl4—O44113.9 (3)
N1C—C1C—C2C116.1 (4)O41—Cl4—O44105.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AN···O1B1.03 (5)1.91 (6)2.741 (6)136 (5)
N2B—H2CN···O1A0.77 (7)2.00 (6)2.742 (5)163 (6)
N2C—H2EN···O1Di0.90 (9)2.00 (9)2.735 (6)138 (8)
N2D—H2GN···O1Cii1.05 (5)1.74 (5)2.754 (5)159 (5)
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AN···O1B1.03 (5)1.91 (6)2.741 (6)136 (5)
N2B—H2CN···O1A0.77 (7)2.00 (6)2.742 (5)163 (6)
N2C—H2EN···O1Di0.90 (9)2.00 (9)2.735 (6)138 (8)
N2D—H2GN···O1Cii1.05 (5)1.74 (5)2.754 (5)159 (5)
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.
 

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA-F7-T185)

References

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o343-o344
https://doi.org/10.1107/S2056989015007781
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