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ISSN: 2056-9890

5-Chloro­spiro­[indoline-3,7′-6H,7H,8H-pyrano[3,2-c:5,6-c′]di[1]benzo­pyran]-2,6′,8′-trione

aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and bDepartment of Physics, The Madura College, Madurai 625 011, India
*Correspondence e-mail: ambujasureshj@yahoo.com

(Received 3 March 2012; accepted 20 March 2012; online 24 March 2012)

The asymmetric unit of the title compound, C26H12ClNO6, consists of two independent mol­ecules. The central pyran rings and both the 1-benzopyran ring systems are nearly planar in both mol­ecules [r.m.s. deviations of pyan rings = 0.0264 (1) and 0.0326 (1) Å for molecules A and B, respectively; r.m.s. deviations of benzopyran rings = 0.0439 (1) and 0.0105 (1) for molecule A, 0.0146 (1) and 0.0262 (1) Å for molecule B]. In the crystal, the molecules are linked by C—H⋯O, N—H⋯O and C—H⋯π inter­actions.

Related literature

The benzopyran structural motif is observed in many biologically active natural products and it plays an important role in binding with various biopolymers, see: Martin & Critchlow (1999[Martin, E. J. & Critchlow, R. E. (1999). J. Combin. Chem. 1, 32-45.]); Teague & Davis (1999[Teague, S. J. & Davis, A. M. (1999). Angew. Chem. Int. Ed. 38, 3743-3748.]). Spiro indoles are known for their broad spectrum of biological activity, see: Joshi & Jain (1985[Joshi, K. C. & Jain, R. (1985). Heterocycles, 23, 957-996.]). For the pharmacological properties of spiro­[indole-pyran]s, see: Ninamiya (1980[Ninamiya, K. (1980). Jpn Patent No. 80164683.]); Kobayashi & Matsuda (1970[Kobayashi, G. & Matsuda, Y. (1970). Jpn Patent No. 7025894.]).

[Scheme 1]

Experimental

Crystal data
  • C26H12ClNO6

  • Mr = 469.82

  • Monoclinic, P 21 /c

  • a = 16.1910 (3) Å

  • b = 12.9931 (3) Å

  • c = 20.8743 (4) Å

  • β = 109.091 (1)°

  • V = 4149.83 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 293 K

  • 0.21 × 0.19 × 0.16 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.978

  • 35770 measured reflections

  • 11888 independent reflections

  • 8559 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.164

  • S = 1.16

  • 11888 reflections

  • 613 parameters

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C13B–C18B, C2B–C7B and C20B–C25B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C22B—H22B⋯O4A 0.93 2.41 3.218 (4) 146
N1A—H1A⋯O6Bi 0.86 2.08 2.810 (3) 142
N1B—H1B⋯O5Bi 0.86 2.12 2.968 (3) 169
C5A—H5A⋯O4Bii 0.93 2.58 3.227 (4) 127
C5B—H5B⋯O5Aiii 0.93 2.27 3.196 (4) 173
C14B—H14B⋯O4Biv 0.93 2.55 3.035 (4) 113
C17A—H17A⋯O6Av 0.93 2.49 3.312 (4) 148
C24A—H24A⋯Cl2vi 0.93 2.69 3.520 (3) 149
C4a—H4a⋯Cg1vi 0.93 2.95 3.832 (4) 158
C6a—H6a⋯Cg2vi 0.93 2.74 3.657 (4) 169
C5a—H5a⋯Cg3ii 0.93 2.88 3.701 (3) 147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) -x, -y, -z+1; (vi) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Benzopyran is a privileged structural motif observed in many biologically active natural products, and it plays an important role in binding with various biopolymers (Martin & Critchlow (1999)). Spiro indoles are known for their broad spectrum of biological activities (Joshi & Jain (1985)). Of the various spiro indoles, spiro[indole-pyran] system attracted attention due to its interesting pharmacological properties (Ninamiya (1980) and Kobayashi & Matsuda (1970)). The biological importance of these heterocycles in conjunction with our research interest, prompted us to synthesize and report the X-ray studies of the title compound in this paper.

The asymmetric unit of the title compound C26 H12 CL N O6, contains two independent molecules (A and B) with almost identical geometry (Fig.1). The central pyrano ring and both the benzopyran rings are planar. In the Indolin-2-one system, the benzene and pyrrole rings are individually planar in both the molecules and make dihedral angles of 2.25 (1)° in molecule A and 2.32 (1)° in molecule B. The indoline-2-one system is perpendicular to the pyrano ring, as can be seen from the dihedral angle [86.56 (1) in molecule A and 87.07 (1) in molecule B]. The sum of the angles at atom N1 of the indolin-2-one moiety is in accordance with sp2-hybridization [359.41 (2) and 360.81 (1) in molecules A and B respectively].

The crystal packing shows large number of N—H···O and C—H···O hydrogen bonds. The molecules A and B have intermolecular contacts through N—H···O bonding and generating the crystal structure by large number of zig zag C—H···O hydrogen bonds (Table 1) (Fig.2). In addition there are three weak C—H···π interactions, viz., C4a—H4a···Cg1vi, C6a—H6a···Cg2vi and C5a—H5a···Cg3 ii, (Cg1, Cg2 and Cg3 are the centroids of the rings C13B—C18B, C2B—C7B and C20B—C25B;symmetry codes are given in Table 1) are observed.

Related literature top

The benzopyran structural motif is observed in many biologically active natural products and it plays an important role in binding with various biopolymers, see: Martin & Critchlow (1999); Teague & Davis (1999). Spiro indoles are known for their broad spectrum of biological activity, see: Joshi & Jain (1985). For the pharmacological properties of spiro[indole-pyran]s, see: Ninamiya (1980); Kobayashi & Matsuda (1970).

Experimental top

A mixture of 5-chloroindoline-2,3-dione (0.100 g, 0.55 mmol), 4-hydroxy-2H-chromen-2-one (0.178 g, 1.10 mmol), and paratoluene sulfonic acid (0.105 g, 0.55 mmol) were dissolved in 5 ml of ethanol:water (1:1 v/v) and refluxed for 2 h. After completion of the reaction as evident from TLC, the precipitated solid was filtered and washed with water to afford the product which was recrystallized from ethanol to reveal the title compound as colourless crystals. Yield 80%, Melting point 276°C

Refinement top

H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93 Å, N—H = 0.86 Å and Uiso = 1.2Ueq(C,N) for CH and NH groups.

Structure description top

Benzopyran is a privileged structural motif observed in many biologically active natural products, and it plays an important role in binding with various biopolymers (Martin & Critchlow (1999)). Spiro indoles are known for their broad spectrum of biological activities (Joshi & Jain (1985)). Of the various spiro indoles, spiro[indole-pyran] system attracted attention due to its interesting pharmacological properties (Ninamiya (1980) and Kobayashi & Matsuda (1970)). The biological importance of these heterocycles in conjunction with our research interest, prompted us to synthesize and report the X-ray studies of the title compound in this paper.

The asymmetric unit of the title compound C26 H12 CL N O6, contains two independent molecules (A and B) with almost identical geometry (Fig.1). The central pyrano ring and both the benzopyran rings are planar. In the Indolin-2-one system, the benzene and pyrrole rings are individually planar in both the molecules and make dihedral angles of 2.25 (1)° in molecule A and 2.32 (1)° in molecule B. The indoline-2-one system is perpendicular to the pyrano ring, as can be seen from the dihedral angle [86.56 (1) in molecule A and 87.07 (1) in molecule B]. The sum of the angles at atom N1 of the indolin-2-one moiety is in accordance with sp2-hybridization [359.41 (2) and 360.81 (1) in molecules A and B respectively].

The crystal packing shows large number of N—H···O and C—H···O hydrogen bonds. The molecules A and B have intermolecular contacts through N—H···O bonding and generating the crystal structure by large number of zig zag C—H···O hydrogen bonds (Table 1) (Fig.2). In addition there are three weak C—H···π interactions, viz., C4a—H4a···Cg1vi, C6a—H6a···Cg2vi and C5a—H5a···Cg3 ii, (Cg1, Cg2 and Cg3 are the centroids of the rings C13B—C18B, C2B—C7B and C20B—C25B;symmetry codes are given in Table 1) are observed.

The benzopyran structural motif is observed in many biologically active natural products and it plays an important role in binding with various biopolymers, see: Martin & Critchlow (1999); Teague & Davis (1999). Spiro indoles are known for their broad spectrum of biological activity, see: Joshi & Jain (1985). For the pharmacological properties of spiro[indole-pyran]s, see: Ninamiya (1980); Kobayashi & Matsuda (1970).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme of molecules A and B.
[Figure 2] Fig. 2. Partial packing diagram of the molecule.
5-Chlorospiro[indoline-3,7'-6H,7H,8H-pyrano[3,2- c:5,6-c']di[1]benzopyran]-2,6',8'-trione top
Crystal data top
C26H12ClNO6F(000) = 1920
Mr = 469.82Dx = 1.504 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2000 reflections
a = 16.1910 (3) Åθ = 2–31°
b = 12.9931 (3) ŵ = 0.23 mm1
c = 20.8743 (4) ÅT = 293 K
β = 109.091 (1)°Block, colourless
V = 4149.83 (15) Å30.21 × 0.19 × 0.16 mm
Z = 8
Data collection top
Bruker Kappa APEXII
diffractometer
11888 independent reflections
Radiation source: fine-focus sealed tube8559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 0 pixels mm-1θmax = 29.9°, θmin = 1.9°
ω and φ scansh = 2222
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1812
Tmin = 0.973, Tmax = 0.978l = 2921
35770 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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0208P)2 + 11.0869P]
where P = (Fo2 + 2Fc2)/3
11888 reflections(Δ/σ)max = 0.001
613 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.80 e Å3
Crystal data top
C26H12ClNO6V = 4149.83 (15) Å3
Mr = 469.82Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.1910 (3) ŵ = 0.23 mm1
b = 12.9931 (3) ÅT = 293 K
c = 20.8743 (4) Å0.21 × 0.19 × 0.16 mm
β = 109.091 (1)°
Data collection top
Bruker Kappa APEXII
diffractometer
11888 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8559 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.978Rint = 0.043
35770 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0790 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0208P)2 + 11.0869P]
where P = (Fo2 + 2Fc2)/3
11888 reflectionsΔρmax = 0.64 e Å3
613 parametersΔρmin = 0.80 e Å3
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
C1A0.01322 (18)0.1554 (2)0.45426 (14)0.0166 (6)
C1B0.38576 (17)0.9265 (2)0.43954 (14)0.0164 (6)
C2A0.07950 (18)0.1436 (2)0.38862 (14)0.0166 (6)
C2B0.36099 (18)1.0100 (2)0.39167 (15)0.0183 (6)
C3A0.16246 (19)0.1007 (2)0.37875 (15)0.0201 (6)
H3A0.17710.07590.41540.024*
C3B0.3500 (2)1.1115 (3)0.40901 (17)0.0246 (7)
H3B0.36201.12960.45420.029*
C4A0.2219 (2)0.0956 (3)0.31394 (16)0.0249 (7)
H4A0.27700.06770.30710.030*
C4B0.3216 (2)1.1844 (3)0.35926 (18)0.0309 (8)
H4B0.31421.25200.37100.037*
C5A0.2002 (2)0.1320 (3)0.25879 (16)0.0256 (7)
H5A0.24100.12820.21550.031*
C5B0.3038 (2)1.1588 (3)0.29149 (18)0.0310 (8)
H5B0.28451.20920.25830.037*
C6A0.1183 (2)0.1737 (3)0.26765 (16)0.0246 (7)
H6A0.10360.19750.23080.030*
C6B0.3145 (2)1.0584 (3)0.27312 (17)0.0276 (7)
H6B0.30271.04070.22780.033*
C7A0.05910 (19)0.1790 (2)0.33282 (15)0.0191 (6)
C7B0.34329 (18)0.9847 (2)0.32374 (15)0.0197 (6)
C8A0.08564 (19)0.2313 (2)0.40185 (15)0.0193 (6)
C8B0.37897 (18)0.8072 (2)0.34880 (15)0.0186 (6)
C9A0.06541 (18)0.1972 (2)0.46159 (14)0.0157 (6)
C9B0.39228 (18)0.8291 (2)0.42029 (14)0.0160 (6)
C10A0.13538 (17)0.2133 (2)0.53026 (14)0.0161 (6)
C10B0.40791 (17)0.7387 (2)0.46806 (14)0.0138 (5)
C11A0.10273 (18)0.1650 (2)0.58321 (14)0.0169 (6)
C11B0.42934 (17)0.7793 (2)0.53972 (14)0.0152 (6)
C12A0.16297 (19)0.1617 (2)0.65275 (15)0.0192 (6)
C12B0.45802 (18)0.7069 (2)0.59557 (15)0.0175 (6)
C13A0.0461 (2)0.0984 (2)0.68946 (15)0.0204 (6)
C13B0.46670 (19)0.8459 (2)0.67352 (15)0.0185 (6)
C14A0.0207 (2)0.0695 (3)0.74419 (16)0.0263 (7)
H14A0.05840.07760.78830.032*
C14B0.4861 (2)0.8739 (3)0.74104 (16)0.0241 (7)
H14B0.50530.82530.77540.029*
C15A0.0614 (2)0.0285 (3)0.73204 (17)0.0294 (8)
H15A0.07920.00900.76840.035*
C15B0.4764 (2)0.9760 (3)0.75593 (16)0.0268 (7)
H15B0.48960.99620.80090.032*
C16A0.1185 (2)0.0157 (3)0.66579 (17)0.0261 (7)
H16A0.17310.01380.65830.031*
C16B0.4471 (2)1.0488 (3)0.70474 (16)0.0251 (7)
H16B0.43981.11680.71570.030*
C17A0.0938 (2)0.0470 (2)0.61155 (16)0.0206 (6)
H17A0.13210.03970.56750.025*
C17B0.4287 (2)1.0207 (2)0.63795 (16)0.0215 (6)
H17B0.40961.06960.60380.026*
C18A0.01047 (19)0.0899 (2)0.62302 (15)0.0176 (6)
C18B0.43903 (18)0.9177 (2)0.62167 (14)0.0169 (6)
C19A0.02145 (18)0.1273 (2)0.57045 (14)0.0162 (6)
C19B0.42236 (17)0.8796 (2)0.55366 (14)0.0160 (6)
C20A0.25197 (18)0.3343 (2)0.55651 (14)0.0177 (6)
C20B0.3603 (2)0.5689 (2)0.43396 (15)0.0228 (7)
C21A0.29529 (19)0.4267 (2)0.57562 (15)0.0198 (6)
H21A0.35470.43230.58180.024*
C21B0.3040 (3)0.4868 (3)0.41425 (17)0.0345 (9)
H21B0.32410.42230.40680.041*
C22A0.2481 (2)0.5107 (2)0.58531 (15)0.0209 (6)
H22A0.27570.57370.59830.025*
C22B0.2164 (3)0.5033 (3)0.40578 (17)0.0385 (10)
H22B0.17690.44910.39280.046*
C23A0.15950 (19)0.5007 (2)0.57560 (15)0.0192 (6)
C23B0.1875 (2)0.5995 (3)0.41641 (16)0.0293 (8)
C24A0.11517 (18)0.4083 (2)0.55557 (14)0.0165 (6)
H24A0.05550.40320.54840.020*
C24B0.24430 (19)0.6822 (3)0.43870 (15)0.0217 (6)
H24B0.22450.74630.44720.026*
C25A0.16235 (18)0.3248 (2)0.54681 (14)0.0161 (6)
C25B0.33124 (18)0.6645 (2)0.44753 (14)0.0161 (6)
C26A0.22395 (18)0.1639 (2)0.53016 (15)0.0187 (6)
C26B0.48296 (19)0.6683 (3)0.46144 (14)0.0195 (6)
N1A0.28499 (15)0.2396 (2)0.54516 (13)0.0204 (5)
H1A0.33840.23010.54740.024*
N1B0.44963 (18)0.5739 (2)0.44268 (13)0.0250 (6)
H1B0.47980.52250.43670.030*
O1A0.03879 (12)0.12121 (16)0.50672 (10)0.0179 (4)
O1B0.39990 (13)0.95531 (16)0.50537 (10)0.0193 (4)
O2A0.02128 (13)0.22147 (17)0.33975 (10)0.0213 (5)
O2B0.35248 (14)0.88599 (17)0.30331 (10)0.0219 (5)
O3A0.12997 (14)0.13474 (18)0.70343 (10)0.0232 (5)
O3B0.47610 (14)0.74300 (17)0.66028 (10)0.0215 (5)
O4A0.15420 (14)0.26765 (18)0.40284 (11)0.0245 (5)
O4B0.38904 (15)0.72334 (18)0.32780 (11)0.0250 (5)
O5A0.23954 (14)0.18162 (19)0.66861 (11)0.0263 (5)
O5B0.46879 (14)0.61531 (17)0.58930 (11)0.0218 (5)
O6A0.23407 (14)0.07422 (17)0.51840 (11)0.0231 (5)
O6B0.55785 (14)0.6966 (2)0.47220 (12)0.0310 (6)
Cl10.10234 (5)0.60744 (6)0.58955 (5)0.03013 (19)
Cl20.07605 (6)0.61968 (10)0.40081 (5)0.0485 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0203 (13)0.0121 (14)0.0164 (13)0.0034 (11)0.0048 (11)0.0011 (11)
C1B0.0121 (12)0.0210 (15)0.0155 (13)0.0015 (11)0.0034 (10)0.0008 (12)
C2A0.0184 (13)0.0122 (14)0.0165 (13)0.0032 (11)0.0023 (11)0.0028 (11)
C2B0.0159 (13)0.0202 (15)0.0179 (14)0.0013 (11)0.0044 (11)0.0003 (12)
C3A0.0199 (14)0.0178 (15)0.0193 (14)0.0013 (12)0.0020 (11)0.0020 (12)
C3B0.0297 (16)0.0223 (16)0.0230 (15)0.0034 (13)0.0104 (13)0.0003 (13)
C4A0.0187 (14)0.0256 (18)0.0252 (16)0.0015 (13)0.0001 (12)0.0026 (13)
C4B0.0375 (19)0.0232 (18)0.0343 (19)0.0066 (15)0.0150 (16)0.0058 (15)
C5A0.0211 (15)0.0285 (18)0.0189 (15)0.0057 (13)0.0049 (12)0.0040 (13)
C5B0.0341 (18)0.0288 (19)0.0290 (18)0.0092 (15)0.0087 (15)0.0146 (15)
C6A0.0287 (16)0.0255 (17)0.0176 (14)0.0083 (14)0.0047 (13)0.0006 (13)
C6B0.0271 (16)0.034 (2)0.0208 (16)0.0021 (14)0.0071 (13)0.0067 (14)
C7A0.0195 (14)0.0140 (14)0.0213 (15)0.0036 (11)0.0032 (12)0.0024 (12)
C7B0.0159 (13)0.0205 (16)0.0220 (15)0.0010 (12)0.0052 (11)0.0001 (12)
C8A0.0226 (15)0.0149 (15)0.0186 (14)0.0025 (12)0.0043 (12)0.0023 (12)
C8B0.0163 (13)0.0211 (16)0.0196 (14)0.0039 (11)0.0075 (11)0.0020 (12)
C9A0.0159 (13)0.0136 (14)0.0142 (13)0.0017 (11)0.0002 (10)0.0002 (11)
C9B0.0159 (13)0.0163 (14)0.0157 (13)0.0009 (11)0.0050 (11)0.0010 (11)
C10A0.0130 (12)0.0148 (14)0.0171 (13)0.0005 (11)0.0005 (11)0.0034 (11)
C10B0.0129 (12)0.0140 (14)0.0133 (13)0.0002 (10)0.0025 (10)0.0028 (11)
C11A0.0184 (13)0.0136 (14)0.0165 (14)0.0019 (11)0.0028 (11)0.0032 (11)
C11B0.0122 (12)0.0172 (14)0.0155 (13)0.0003 (11)0.0036 (10)0.0014 (11)
C12A0.0209 (14)0.0158 (15)0.0152 (13)0.0020 (12)0.0020 (11)0.0018 (11)
C12B0.0163 (13)0.0184 (15)0.0181 (14)0.0005 (11)0.0059 (11)0.0008 (12)
C13A0.0239 (15)0.0161 (15)0.0193 (14)0.0039 (12)0.0045 (12)0.0022 (12)
C13B0.0193 (13)0.0189 (15)0.0176 (14)0.0021 (12)0.0063 (11)0.0035 (12)
C14A0.0308 (17)0.0297 (19)0.0150 (14)0.0064 (14)0.0029 (13)0.0009 (13)
C14B0.0256 (16)0.0293 (18)0.0170 (14)0.0015 (13)0.0062 (12)0.0001 (13)
C15A0.0354 (18)0.032 (2)0.0237 (16)0.0046 (15)0.0142 (14)0.0041 (15)
C15B0.0273 (16)0.036 (2)0.0180 (15)0.0039 (14)0.0094 (13)0.0089 (14)
C16A0.0231 (15)0.0278 (18)0.0294 (17)0.0020 (13)0.0112 (13)0.0024 (14)
C16B0.0255 (16)0.0260 (18)0.0247 (16)0.0013 (13)0.0094 (13)0.0093 (14)
C17A0.0215 (14)0.0187 (15)0.0208 (15)0.0040 (12)0.0061 (12)0.0003 (12)
C17B0.0230 (15)0.0195 (16)0.0214 (15)0.0020 (12)0.0064 (12)0.0016 (12)
C18A0.0212 (14)0.0138 (14)0.0162 (13)0.0039 (11)0.0040 (11)0.0015 (11)
C18B0.0147 (12)0.0199 (15)0.0151 (13)0.0001 (11)0.0037 (10)0.0016 (11)
C19A0.0190 (13)0.0128 (14)0.0131 (13)0.0040 (11)0.0001 (11)0.0009 (11)
C19B0.0138 (12)0.0183 (15)0.0150 (13)0.0017 (11)0.0036 (10)0.0012 (11)
C20A0.0172 (13)0.0214 (16)0.0128 (13)0.0021 (12)0.0028 (11)0.0001 (11)
C20B0.0309 (16)0.0190 (16)0.0129 (13)0.0017 (13)0.0003 (12)0.0008 (12)
C21A0.0156 (13)0.0221 (16)0.0197 (14)0.0039 (12)0.0030 (11)0.0022 (12)
C21B0.055 (2)0.0192 (17)0.0197 (16)0.0039 (16)0.0009 (16)0.0003 (14)
C22A0.0256 (15)0.0165 (15)0.0183 (14)0.0061 (12)0.0039 (12)0.0020 (12)
C22B0.049 (2)0.037 (2)0.0187 (16)0.0265 (18)0.0026 (15)0.0036 (15)
C23A0.0241 (15)0.0153 (15)0.0163 (14)0.0055 (12)0.0040 (12)0.0011 (11)
C23B0.0210 (15)0.047 (2)0.0162 (15)0.0158 (15)0.0008 (12)0.0042 (15)
C24A0.0148 (12)0.0186 (15)0.0143 (13)0.0019 (11)0.0022 (10)0.0005 (11)
C24B0.0216 (14)0.0281 (17)0.0148 (14)0.0030 (13)0.0052 (11)0.0020 (12)
C25A0.0144 (12)0.0161 (14)0.0153 (13)0.0015 (11)0.0015 (10)0.0015 (11)
C25B0.0167 (13)0.0173 (15)0.0103 (12)0.0017 (11)0.0010 (10)0.0010 (11)
C26A0.0173 (13)0.0201 (16)0.0154 (13)0.0037 (12)0.0009 (11)0.0011 (12)
C26B0.0193 (14)0.0253 (16)0.0119 (13)0.0088 (12)0.0023 (11)0.0003 (12)
N1A0.0124 (11)0.0210 (14)0.0261 (13)0.0031 (10)0.0039 (10)0.0051 (11)
N1B0.0331 (15)0.0192 (14)0.0196 (13)0.0118 (11)0.0044 (11)0.0027 (11)
O1A0.0158 (9)0.0202 (11)0.0150 (10)0.0020 (8)0.0013 (8)0.0001 (8)
O1B0.0254 (11)0.0154 (10)0.0165 (10)0.0042 (9)0.0062 (8)0.0013 (8)
O2A0.0227 (11)0.0213 (12)0.0177 (10)0.0002 (9)0.0039 (8)0.0007 (9)
O2B0.0281 (11)0.0219 (12)0.0154 (10)0.0015 (9)0.0067 (9)0.0010 (9)
O3A0.0233 (11)0.0259 (12)0.0163 (10)0.0015 (9)0.0007 (8)0.0023 (9)
O3B0.0282 (11)0.0198 (11)0.0154 (10)0.0018 (9)0.0056 (9)0.0004 (9)
O4A0.0230 (11)0.0251 (12)0.0259 (12)0.0039 (9)0.0087 (9)0.0026 (10)
O4B0.0314 (12)0.0235 (12)0.0214 (11)0.0007 (10)0.0105 (9)0.0055 (9)
O5A0.0213 (11)0.0292 (13)0.0226 (11)0.0016 (9)0.0009 (9)0.0052 (10)
O5B0.0286 (11)0.0167 (11)0.0202 (10)0.0037 (9)0.0080 (9)0.0030 (9)
O6A0.0218 (10)0.0187 (11)0.0252 (11)0.0047 (9)0.0027 (9)0.0050 (9)
O6B0.0177 (11)0.0433 (15)0.0327 (13)0.0078 (10)0.0094 (10)0.0036 (12)
Cl10.0336 (4)0.0175 (4)0.0383 (5)0.0069 (3)0.0103 (4)0.0062 (3)
Cl20.0240 (4)0.0915 (9)0.0294 (5)0.0267 (5)0.0078 (3)0.0005 (5)
Geometric parameters (Å, º) top
C1A—C9A1.346 (4)C13A—C18A1.394 (4)
C1A—O1A1.366 (3)C13B—O3B1.384 (4)
C1A—C2A1.446 (4)C13B—C18B1.387 (4)
C1B—C9B1.342 (4)C13B—C14B1.388 (4)
C1B—O1B1.369 (3)C14A—C15A1.376 (5)
C1B—C2B1.440 (4)C14A—H14A0.9300
C2A—C7A1.389 (4)C14B—C15B1.382 (5)
C2A—C3A1.406 (4)C14B—H14B0.9300
C2B—C7B1.391 (4)C15A—C16A1.399 (5)
C2B—C3B1.394 (4)C15A—H15A0.9300
C3A—C4A1.382 (4)C15B—C16B1.389 (5)
C3A—H3A0.9300C15B—H15B0.9300
C3B—C4B1.369 (5)C16A—C17A1.379 (4)
C3B—H3B0.9300C16A—H16A0.9300
C4A—C5A1.392 (5)C16B—C17B1.377 (4)
C4A—H4A0.9300C16B—H16B0.9300
C4B—C5B1.388 (5)C17A—C18A1.406 (4)
C4B—H4B0.9300C17A—H17A0.9300
C5A—C6A1.387 (5)C17B—C18B1.404 (4)
C5A—H5A0.9300C17B—H17B0.9300
C5B—C6B1.387 (5)C18A—C19A1.442 (4)
C5B—H5B0.9300C18B—C19B1.443 (4)
C6A—C7A1.386 (4)C19A—O1A1.371 (3)
C6A—H6A0.9300C19B—O1B1.369 (3)
C6B—C7B1.389 (4)C20A—C21A1.382 (4)
C6B—H6B0.9300C20A—N1A1.392 (4)
C7A—O2A1.377 (4)C20A—C25A1.403 (4)
C7B—O2B1.374 (4)C20B—C21B1.376 (5)
C8A—O4A1.200 (4)C20B—C25B1.390 (4)
C8A—O2A1.378 (3)C20B—N1B1.399 (4)
C8A—C9A1.458 (4)C21A—C22A1.385 (4)
C8B—O4B1.206 (4)C21A—H21A0.9300
C8B—O2B1.366 (4)C21B—C22B1.388 (6)
C8B—C9B1.464 (4)C21B—H21B0.9300
C9A—C10A1.523 (4)C22A—C23A1.388 (4)
C9B—C10B1.508 (4)C22A—H22A0.9300
C10A—C11A1.509 (4)C22B—C23B1.377 (6)
C10A—C25A1.520 (4)C22B—H22B0.9300
C10A—C26A1.572 (4)C23A—C24A1.391 (4)
C10B—C11B1.516 (4)C23A—Cl11.744 (3)
C10B—C25B1.518 (4)C23B—C24B1.392 (5)
C10B—C26B1.563 (4)C23B—Cl21.746 (3)
C11A—C19A1.347 (4)C24A—C25A1.372 (4)
C11A—C12A1.461 (4)C24A—H24A0.9300
C11B—C19B1.348 (4)C24B—C25B1.378 (4)
C11B—C12B1.451 (4)C24B—H24B0.9300
C12A—O5A1.202 (4)C26A—O6A1.214 (4)
C12A—O3A1.377 (4)C26A—N1A1.356 (4)
C12B—O5B1.216 (4)C26B—O6B1.216 (4)
C12B—O3B1.368 (4)C26B—N1B1.346 (4)
C13A—O3A1.376 (4)N1A—H1A0.8600
C13A—C14A1.387 (4)N1B—H1B0.8600
C9A—C1A—O1A124.3 (3)C15B—C14B—C13B118.3 (3)
C9A—C1A—C2A122.1 (3)C15B—C14B—H14B120.8
O1A—C1A—C2A113.6 (2)C13B—C14B—H14B120.8
C9B—C1B—O1B123.7 (3)C14A—C15A—C16A120.9 (3)
C9B—C1B—C2B122.3 (3)C14A—C15A—H15A119.6
O1B—C1B—C2B114.0 (3)C16A—C15A—H15A119.6
C7A—C2A—C3A119.1 (3)C14B—C15B—C16B121.0 (3)
C7A—C2A—C1A117.0 (3)C14B—C15B—H15B119.5
C3A—C2A—C1A123.9 (3)C16B—C15B—H15B119.5
C7B—C2B—C3B119.1 (3)C17A—C16A—C15A120.1 (3)
C7B—C2B—C1B116.5 (3)C17A—C16A—H16A119.9
C3B—C2B—C1B124.2 (3)C15A—C16A—H16A119.9
C4A—C3A—C2A119.2 (3)C17B—C16B—C15B120.3 (3)
C4A—C3A—H3A120.4C17B—C16B—H16B119.9
C2A—C3A—H3A120.4C15B—C16B—H16B119.9
C4B—C3B—C2B119.8 (3)C16A—C17A—C18A119.8 (3)
C4B—C3B—H3B120.1C16A—C17A—H17A120.1
C2B—C3B—H3B120.1C18A—C17A—H17A120.1
C3A—C4A—C5A120.7 (3)C16B—C17B—C18B119.6 (3)
C3A—C4A—H4A119.7C16B—C17B—H17B120.2
C5A—C4A—H4A119.7C18B—C17B—H17B120.2
C3B—C4B—C5B120.9 (3)C13A—C18A—C17A118.8 (3)
C3B—C4B—H4B119.5C13A—C18A—C19A116.6 (3)
C5B—C4B—H4B119.5C17A—C18A—C19A124.5 (3)
C6A—C5A—C4A120.8 (3)C13B—C18B—C17B119.0 (3)
C6A—C5A—H5A119.6C13B—C18B—C19B116.5 (3)
C4A—C5A—H5A119.6C17B—C18B—C19B124.5 (3)
C6B—C5B—C4B120.2 (3)C11A—C19A—O1A123.5 (3)
C6B—C5B—H5B119.9C11A—C19A—C18A122.9 (3)
C4B—C5B—H5B119.9O1A—C19A—C18A113.6 (2)
C7A—C6A—C5A118.3 (3)C11B—C19B—O1B123.8 (3)
C7A—C6A—H6A120.8C11B—C19B—C18B122.8 (3)
C5A—C6A—H6A120.8O1B—C19B—C18B113.4 (3)
C5B—C6B—C7B118.7 (3)C21A—C20A—N1A129.0 (3)
C5B—C6B—H6B120.7C21A—C20A—C25A121.4 (3)
C7B—C6B—H6B120.7N1A—C20A—C25A109.6 (3)
O2A—C7A—C6A116.7 (3)C21B—C20B—C25B121.3 (3)
O2A—C7A—C2A121.4 (3)C21B—C20B—N1B129.0 (3)
C6A—C7A—C2A121.9 (3)C25B—C20B—N1B109.7 (3)
O2B—C7B—C6B116.8 (3)C20A—C21A—C22A118.4 (3)
O2B—C7B—C2B122.0 (3)C20A—C21A—H21A120.8
C6B—C7B—C2B121.2 (3)C22A—C21A—H21A120.8
O4A—C8A—O2A117.6 (3)C20B—C21B—C22B117.8 (4)
O4A—C8A—C9A124.8 (3)C20B—C21B—H21B121.1
O2A—C8A—C9A117.6 (3)C22B—C21B—H21B121.1
O4B—C8B—O2B118.3 (3)C21A—C22A—C23A119.9 (3)
O4B—C8B—C9B123.6 (3)C21A—C22A—H22A120.1
O2B—C8B—C9B118.1 (3)C23A—C22A—H22A120.1
C1A—C9A—C8A119.6 (3)C23B—C22B—C21B120.5 (3)
C1A—C9A—C10A123.2 (3)C23B—C22B—H22B119.8
C8A—C9A—C10A117.2 (2)C21B—C22B—H22B119.8
C1B—C9B—C8B119.2 (3)C22A—C23A—C24A122.1 (3)
C1B—C9B—C10B123.3 (3)C22A—C23A—Cl1118.7 (2)
C8B—C9B—C10B117.4 (3)C24A—C23A—Cl1119.1 (2)
C11A—C10A—C25A111.9 (2)C22B—C23B—C24B122.2 (3)
C11A—C10A—C9A107.5 (2)C22B—C23B—Cl2119.4 (3)
C25A—C10A—C9A114.5 (2)C24B—C23B—Cl2118.4 (3)
C11A—C10A—C26A111.7 (2)C25A—C24A—C23A117.8 (3)
C25A—C10A—C26A101.2 (2)C25A—C24A—H24A121.1
C9A—C10A—C26A109.9 (2)C23A—C24A—H24A121.1
C9B—C10B—C11B108.4 (2)C25B—C24B—C23B116.8 (3)
C9B—C10B—C25B111.3 (2)C25B—C24B—H24B121.6
C11B—C10B—C25B113.7 (2)C23B—C24B—H24B121.6
C9B—C10B—C26B111.4 (2)C24A—C25A—C20A120.4 (3)
C11B—C10B—C26B110.9 (2)C24A—C25A—C10A130.7 (3)
C25B—C10B—C26B101.0 (2)C20A—C25A—C10A108.8 (2)
C19A—C11A—C12A118.5 (3)C24B—C25B—C20B121.4 (3)
C19A—C11A—C10A124.1 (3)C24B—C25B—C10B129.6 (3)
C12A—C11A—C10A117.4 (3)C20B—C25B—C10B108.9 (3)
C19B—C11B—C12B118.7 (3)O6A—C26A—N1A127.4 (3)
C19B—C11B—C10B122.8 (3)O6A—C26A—C10A125.2 (3)
C12B—C11B—C10B118.5 (3)N1A—C26A—C10A107.5 (2)
O5A—C12A—O3A117.9 (3)O6B—C26B—N1B127.6 (3)
O5A—C12A—C11A124.1 (3)O6B—C26B—C10B124.3 (3)
O3A—C12A—C11A118.0 (3)N1B—C26B—C10B108.0 (2)
O5B—C12B—O3B116.7 (3)C26A—N1A—C20A112.9 (2)
O5B—C12B—C11B124.6 (3)C26A—N1A—H1A123.6
O3B—C12B—C11B118.7 (3)C20A—N1A—H1A123.6
O3A—C13A—C14A117.2 (3)C26B—N1B—C20B112.2 (3)
O3A—C13A—C18A121.3 (3)C26B—N1B—H1B123.9
C14A—C13A—C18A121.5 (3)C20B—N1B—H1B123.9
O3B—C13B—C18B121.5 (3)C1A—O1A—C19A117.0 (2)
O3B—C13B—C14B116.9 (3)C1B—O1B—C19B117.3 (2)
C18B—C13B—C14B121.6 (3)C7A—O2A—C8A122.3 (2)
C15A—C14A—C13A118.8 (3)C8B—O2B—C7B121.6 (2)
C15A—C14A—H14A120.6C13A—O3A—C12A121.9 (2)
C13A—C14A—H14A120.6C12B—O3B—C13B121.8 (2)
C9A—C1A—C2A—C7A1.0 (4)C16B—C17B—C18B—C19B179.6 (3)
O1A—C1A—C2A—C7A178.5 (2)C12A—C11A—C19A—O1A176.2 (3)
C9A—C1A—C2A—C3A179.9 (3)C10A—C11A—C19A—O1A5.3 (5)
O1A—C1A—C2A—C3A0.4 (4)C12A—C11A—C19A—C18A4.1 (4)
C9B—C1B—C2B—C7B0.5 (4)C10A—C11A—C19A—C18A174.4 (3)
O1B—C1B—C2B—C7B178.2 (2)C13A—C18A—C19A—C11A2.7 (4)
C9B—C1B—C2B—C3B177.4 (3)C17A—C18A—C19A—C11A177.9 (3)
O1B—C1B—C2B—C3B1.3 (4)C13A—C18A—C19A—O1A177.1 (3)
C7A—C2A—C3A—C4A0.7 (4)C17A—C18A—C19A—O1A2.4 (4)
C1A—C2A—C3A—C4A178.2 (3)C12B—C11B—C19B—O1B176.9 (2)
C7B—C2B—C3B—C4B0.4 (5)C10B—C11B—C19B—O1B3.6 (4)
C1B—C2B—C3B—C4B176.4 (3)C12B—C11B—C19B—C18B2.4 (4)
C2A—C3A—C4A—C5A0.4 (5)C10B—C11B—C19B—C18B177.2 (3)
C2B—C3B—C4B—C5B0.3 (5)C13B—C18B—C19B—C11B2.7 (4)
C3A—C4A—C5A—C6A0.2 (5)C17B—C18B—C19B—C11B177.0 (3)
C3B—C4B—C5B—C6B0.0 (5)C13B—C18B—C19B—O1B176.6 (2)
C4A—C5A—C6A—C7A0.5 (5)C17B—C18B—C19B—O1B3.6 (4)
C4B—C5B—C6B—C7B0.1 (5)N1A—C20A—C21A—C22A178.6 (3)
C5A—C6A—C7A—O2A179.6 (3)C25A—C20A—C21A—C22A0.2 (4)
C5A—C6A—C7A—C2A0.2 (5)C25B—C20B—C21B—C22B2.4 (5)
C3A—C2A—C7A—O2A179.8 (3)N1B—C20B—C21B—C22B176.6 (3)
C1A—C2A—C7A—O2A1.2 (4)C20A—C21A—C22A—C23A0.2 (4)
C3A—C2A—C7A—C6A0.4 (4)C20B—C21B—C22B—C23B0.5 (5)
C1A—C2A—C7A—C6A178.6 (3)C21A—C22A—C23A—C24A0.6 (5)
C5B—C6B—C7B—O2B179.6 (3)C21A—C22A—C23A—Cl1179.0 (2)
C5B—C6B—C7B—C2B0.1 (5)C21B—C22B—C23B—C24B2.9 (5)
C3B—C2B—C7B—O2B179.8 (3)C21B—C22B—C23B—Cl2176.5 (3)
C1B—C2B—C7B—O2B2.7 (4)C22A—C23A—C24A—C25A1.4 (4)
C3B—C2B—C7B—C6B0.4 (4)Cl1—C23A—C24A—C25A178.2 (2)
C1B—C2B—C7B—C6B176.7 (3)C22B—C23B—C24B—C25B2.2 (5)
O1A—C1A—C9A—C8A179.9 (3)Cl2—C23B—C24B—C25B177.2 (2)
C2A—C1A—C9A—C8A0.5 (4)C23A—C24A—C25A—C20A1.4 (4)
O1A—C1A—C9A—C10A1.2 (5)C23A—C24A—C25A—C10A175.3 (3)
C2A—C1A—C9A—C10A178.2 (3)C21A—C20A—C25A—C24A0.6 (4)
O4A—C8A—C9A—C1A178.5 (3)N1A—C20A—C25A—C24A179.6 (3)
O2A—C8A—C9A—C1A1.7 (4)C21A—C20A—C25A—C10A176.7 (3)
O4A—C8A—C9A—C10A2.7 (4)N1A—C20A—C25A—C10A2.3 (3)
O2A—C8A—C9A—C10A177.0 (2)C11A—C10A—C25A—C24A59.6 (4)
O1B—C1B—C9B—C8B177.7 (2)C9A—C10A—C25A—C24A63.1 (4)
C2B—C1B—C9B—C8B3.8 (4)C26A—C10A—C25A—C24A178.7 (3)
O1B—C1B—C9B—C10B5.8 (4)C11A—C10A—C25A—C20A117.4 (3)
C2B—C1B—C9B—C10B172.8 (3)C9A—C10A—C25A—C20A119.9 (3)
O4B—C8B—C9B—C1B175.1 (3)C26A—C10A—C25A—C20A1.7 (3)
O2B—C8B—C9B—C1B5.9 (4)C23B—C24B—C25B—C20B0.8 (4)
O4B—C8B—C9B—C10B8.2 (4)C23B—C24B—C25B—C10B177.1 (3)
O2B—C8B—C9B—C10B170.8 (2)C21B—C20B—C25B—C24B3.1 (5)
C1A—C9A—C10A—C11A5.6 (4)N1B—C20B—C25B—C24B176.0 (3)
C8A—C9A—C10A—C11A175.7 (2)C21B—C20B—C25B—C10B179.9 (3)
C1A—C9A—C10A—C25A119.4 (3)N1B—C20B—C25B—C10B1.0 (3)
C8A—C9A—C10A—C25A59.3 (3)C9B—C10B—C25B—C24B56.8 (4)
C1A—C9A—C10A—C26A127.4 (3)C11B—C10B—C25B—C24B65.9 (4)
C8A—C9A—C10A—C26A53.9 (3)C26B—C10B—C25B—C24B175.2 (3)
C1B—C9B—C10B—C11B9.3 (4)C9B—C10B—C25B—C20B119.8 (3)
C8B—C9B—C10B—C11B174.1 (2)C11B—C10B—C25B—C20B117.4 (3)
C1B—C9B—C10B—C25B116.4 (3)C26B—C10B—C25B—C20B1.5 (3)
C8B—C9B—C10B—C25B60.2 (3)C11A—C10A—C26A—O6A61.6 (4)
C1B—C9B—C10B—C26B131.7 (3)C25A—C10A—C26A—O6A179.2 (3)
C8B—C9B—C10B—C26B51.8 (3)C9A—C10A—C26A—O6A57.7 (4)
C25A—C10A—C11A—C19A119.0 (3)C11A—C10A—C26A—N1A118.6 (3)
C9A—C10A—C11A—C19A7.6 (4)C25A—C10A—C26A—N1A0.6 (3)
C26A—C10A—C11A—C19A128.3 (3)C9A—C10A—C26A—N1A122.1 (3)
C25A—C10A—C11A—C12A59.5 (3)C9B—C10B—C26B—O6B60.6 (4)
C9A—C10A—C11A—C12A173.9 (2)C11B—C10B—C26B—O6B60.3 (4)
C26A—C10A—C11A—C12A53.2 (3)C25B—C10B—C26B—O6B178.8 (3)
C9B—C10B—C11B—C19B8.3 (4)C9B—C10B—C26B—N1B119.8 (3)
C25B—C10B—C11B—C19B116.1 (3)C11B—C10B—C26B—N1B119.3 (3)
C26B—C10B—C11B—C19B130.9 (3)C25B—C10B—C26B—N1B1.6 (3)
C9B—C10B—C11B—C12B172.2 (2)O6A—C26A—N1A—C20A179.5 (3)
C25B—C10B—C11B—C12B63.5 (3)C10A—C26A—N1A—C20A0.7 (3)
C26B—C10B—C11B—C12B49.6 (3)C21A—C20A—N1A—C26A176.9 (3)
C19A—C11A—C12A—O5A170.8 (3)C25A—C20A—N1A—C26A1.9 (4)
C10A—C11A—C12A—O5A10.6 (4)O6B—C26B—N1B—C20B179.3 (3)
C19A—C11A—C12A—O3A9.7 (4)C10B—C26B—N1B—C20B1.1 (3)
C10A—C11A—C12A—O3A168.8 (3)C21B—C20B—N1B—C26B179.0 (3)
C19B—C11B—C12B—O5B178.1 (3)C25B—C20B—N1B—C26B0.1 (4)
C10B—C11B—C12B—O5B2.3 (4)C9A—C1A—O1A—C19A2.2 (4)
C19B—C11B—C12B—O3B0.6 (4)C2A—C1A—O1A—C19A178.3 (2)
C10B—C11B—C12B—O3B179.0 (2)C11A—C19A—O1A—C1A0.2 (4)
O3A—C13A—C14A—C15A177.2 (3)C18A—C19A—O1A—C1A179.9 (2)
C18A—C13A—C14A—C15A2.1 (5)C9B—C1B—O1B—C19B0.4 (4)
O3B—C13B—C14B—C15B179.2 (3)C2B—C1B—O1B—C19B179.0 (2)
C18B—C13B—C14B—C15B0.7 (5)C11B—C19B—O1B—C1B1.4 (4)
C13A—C14A—C15A—C16A0.1 (5)C18B—C19B—O1B—C1B177.9 (2)
C13B—C14B—C15B—C16B0.6 (5)C6A—C7A—O2A—C8A179.8 (3)
C14A—C15A—C16A—C17A1.8 (5)C2A—C7A—O2A—C8A0.0 (4)
C14B—C15B—C16B—C17B1.2 (5)O4A—C8A—O2A—C7A178.7 (3)
C15A—C16A—C17A—C18A1.2 (5)C9A—C8A—O2A—C7A1.5 (4)
C15B—C16B—C17B—C18B0.5 (5)O4B—C8B—O2B—C7B177.1 (3)
O3A—C13A—C18A—C17A176.6 (3)C9B—C8B—O2B—C7B3.8 (4)
C14A—C13A—C18A—C17A2.7 (5)C6B—C7B—O2B—C8B178.9 (3)
O3A—C13A—C18A—C19A4.0 (4)C2B—C7B—O2B—C8B0.5 (4)
C14A—C13A—C18A—C19A176.8 (3)C14A—C13A—O3A—C12A177.4 (3)
C16A—C17A—C18A—C13A1.0 (4)C18A—C13A—O3A—C12A1.9 (4)
C16A—C17A—C18A—C19A178.4 (3)O5A—C12A—O3A—C13A171.7 (3)
O3B—C13B—C18B—C17B178.6 (3)C11A—C12A—O3A—C13A8.8 (4)
C14B—C13B—C18B—C17B1.4 (4)O5B—C12B—O3B—C13B179.6 (3)
O3B—C13B—C18B—C19B1.2 (4)C11B—C12B—O3B—C13B0.8 (4)
C14B—C13B—C18B—C19B178.9 (3)C18B—C13B—O3B—C12B0.5 (4)
C16B—C17B—C18B—C13B0.7 (4)C14B—C13B—O3B—C12B179.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C13B–C18B, C2B–C7B and C20B–C25B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22B—H22B···O4A0.932.413.218 (4)146
N1A—H1A···O6Bi0.862.082.810 (3)142
N1B—H1B···O5Bi0.862.122.968 (3)169
C5A—H5A···O4Bii0.932.583.227 (4)127
C5B—H5B···O5Aiii0.932.273.196 (4)173
C14B—H14B···O4Biv0.932.553.035 (4)113
C17A—H17A···O6Av0.932.493.312 (4)148
C24A—H24A···Cl2vi0.932.693.520 (3)149
C4a—H4a···Cg1vi0.932.953.832 (4)158
C6a—H6a···Cg2vi0.932.743.657 (4)169
C5a—H5a···Cg3ii0.932.883.701 (3)147
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x, y+3/2, z+1/2; (v) x, y, z+1; (vi) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H12ClNO6
Mr469.82
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.1910 (3), 12.9931 (3), 20.8743 (4)
β (°) 109.091 (1)
V3)4149.83 (15)
Z8
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.21 × 0.19 × 0.16
Data collection
DiffractometerBruker Kappa APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.973, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
35770, 11888, 8559
Rint0.043
(sin θ/λ)max1)0.701
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.164, 1.16
No. of reflections11888
No. of parameters613
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0208P)2 + 11.0869P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.64, 0.80

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C13B–C18B, C2B–C7B and C20B–C25B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22B—H22B···O4A0.932.413.218 (4)146
N1A—H1A···O6Bi0.862.082.810 (3)142
N1B—H1B···O5Bi0.862.122.968 (3)169
C5A—H5A···O4Bii0.932.583.227 (4)127
C5B—H5B···O5Aiii0.932.273.196 (4)173
C14B—H14B···O4Biv0.932.553.035 (4)113
C17A—H17A···O6Av0.932.493.312 (4)148
C24A—H24A···Cl2vi0.932.693.520 (3)149
C4a—H4a···Cg1vi0.932.953.832 (4)158
C6a—H6a···Cg2vi0.932.743.657 (4)169
C5a—H5a···Cg3ii0.932.883.701 (3)147
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x, y+3/2, z+1/2; (v) x, y, z+1; (vi) x, y+1, z+1.
 

Acknowledgements

This project was supported by the Research Center, College of Science, King Saud University.

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJoshi, K. C. & Jain, R. (1985). Heterocycles, 23, 957–996.  CAS Google Scholar
First citationKobayashi, G. & Matsuda, Y. (1970). Jpn Patent No. 7025894.  Google Scholar
First citationMartin, E. J. & Critchlow, R. E. (1999). J. Combin. Chem. 1, 32–45.  Web of Science CrossRef CAS Google Scholar
First citationNinamiya, K. (1980). Jpn Patent No. 80164683.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTeague, S. J. & Davis, A. M. (1999). Angew. Chem. Int. Ed. 38, 3743–3748.  Web of Science CrossRef CAS Google Scholar

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