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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 1| January 2014| Pages o97-o98

10-(4-Chloro­phen­yl)-14a-hy­dr­oxy-12-methyl-8,9,9a,10,12,13,14,14a-octa­hydro-5H-10a,14-methano­indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

aDepartment of Physics, The Madura College, Madurai 625 011, India, bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 4 October 2013; accepted 18 December 2013; online 24 December 2013)

The asymmetric unit of the title compound, C26H25ClN2O3, contains two independent mol­ecules (A and B). The conformation of the two mol­ecules differs essentially in the dihedral angle involving the two benzene rings. They are inclined to one another by 52.47 (10) in A and by 31.75 (11)° in B. In both mol­ecules, the six-membered piperidin-3-one rings have chair conformations. In mol­ecule A, all four five-membered rings have twist conformations. In mol­ecule B, only three of the four five-membered rings have twist conformations. The fourth, of the inden-1-one moiety, has an envelope conformation with the spiro C atom, bonded to the N atom of the pyrrolidine ring, as the flap. A weak intra­molecular O—H⋯N hydrogen bond occurs in each independent mol­ecule while a C—H⋯O inter­action is also observed in mol­ecule A. In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules, forming inversion dimers with graph-set motif R22(12). These dimers are further inter­connected by C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.

Related literature

For the importance of pyrrolizine derivatives, see: Anderson & Corey (1977[Anderson, W. K. & Corey, P. F. (1977). J. Med. Chem. 20, 812-818.]); Makoni & Sugden (1980[Makoni, S. H. & Sugden, J. K. (1980). Arzneimittelforschung, 30, 1135-1137.]); Barsoum & Nawar (2003[Barsoum, F. F. & Nawar, N. N. (2003). Boll. Chim. Farm. 142, 160-166.]); Abbas et al. (2010[Abbas, S. E., Awadallah, F. M., Ibrahim, N. A. & Gouda, A. M. (2010). Eur. J. Med. Chem. 45, 482-491.]). For the importance of piperidines, see: Rubiralta et al. (1991[Rubiralta, M., Giralt, E. & Diez, A. (1991). Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives, pp. 225-312. Amsterdam: Elsevier.]); Pinder (1992[Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.]); Michael (2001[Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, edited by G. A. Cordell, Vol. 55, pp. 91-258. New York: Academic Press.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25ClN2O3

  • Mr = 448.93

  • Monoclinic, P 21 /n

  • a = 13.5839 (4) Å

  • b = 11.3764 (4) Å

  • c = 28.5382 (9) Å

  • β = 95.120 (2)°

  • V = 4392.6 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 85408 measured reflections

  • 10365 independent reflections

  • 7088 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.123

  • S = 1.01

  • 10365 reflections

  • 591 parameters

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C21A–C26A ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1A⋯N2A 0.82 2.20 2.705 (2) 120
O1B—H1B⋯N2B 0.82 2.16 2.689 (2) 123
C8A—H8A⋯O2A 0.98 2.57 3.190 (2) 122
O1B—H1B⋯O3Bi 0.82 2.51 3.147 (2) 135
C1A—H3⋯O3Bii 0.96 (3) 2.59 (3) 3.164 (3) 118 (2)
C1A—H2⋯Cg1iii 1.02 (3) 2.70 (3) 3.648 (3) 155 (2)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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

Pyrrolizine derivatives have antimicrobial (Barsoum & Nawar, 2003), anti- inflammatory (Abbas et al., 2010) and antileukemic (Anderson & Corey, 1977) activities. These derivatives are used as inhibitors of blood platelet aggregation (Makoni & Sugden, 1980), Functionalized piperidines are familiar substructures found in biologically active natural products and synthetic pharmaceuticals (Michael, 2001; Pinder, 1992; Rubiralta et al., 1991). Against this background and to ascertain the molecular structure and conformation, the X-ray crystal structure determination of the title compound has been carried out.

The asymmetric unit of the title compound (Fig 1) C37H28N2O3, comprises two independent molecules. In the pyrrazoline ring system, the pyrrolidine rings (N2/C8/C7/C5/C12) adopt twisted conformations with the puckering parameters q2 = 0.4373 (18) Å and Φ2 = 13.0 (2) ° and q2 = 0.4096 (19) Å and Φ2 = 193.9 (3)° (Cremer & Pople, 1975), in molecule A and in molecule B respectively. The pyrrolidine rings (N2/C8—C11) adopt twisted conformation with the puckering parameters q2 = 0.453 (2) Å, Φ2 = 194.8 (3) ° and q2 = 0.461 (2) Å, Φ2 = 10.9 (3) ° (Cremer & Pople, 1975) respectively for molecule A and molecule B. The cyclopentane ring (C12A—C16A) in molecule A adopts a twisted conformation with the puckering parameters q2 = 0.0775 (19) Å and Φ2 = 18.0 (1) ° (Cremer & Pople, 1975). The cyclopentane ring (C12B—C16B) in molecule B adopts an envelop conformation with the puckering parameters q2 = 0.111 (2) Å and Φ2 = 186.4 (12) ° (Cremer & Pople, 1975). The C16—O2 distances in the indolone, in molecules A and B are 1.212 (2) ° and 1.208 (2) A °, respectively. The deviation of O2 from planarity seems to have considerably influenced, the torsion angles N2—C12–C16—O2 and C17—C15—C16—O2 (55.3 (2) ° and 7.2 (2)° in molecule A and -59.4 (2) ° and -1.1 (4)° in molecule B). The differences in these torsion angles may also be attributed due to O1—H1—N2 interaction in molecules A and B. The piperidine ring (N1/C2—C6) adopts a slightly twisted chair conformation in both molecules with the puckering parameters of Q = 0.668 (2) Å, Θ = 166.48 (2) ° and Φ = 22.0 (7) ° in molecule A, Q = 0.161 (2) Å, Θ = 13.97 (17)° and Φ = 203.5 (8) ° in molecule B (Cremer & Pople, 1975). Short contacts H26 ··· H8 (2.17 Å for molecule A and 2.20 Å for molecule B) result in substantial widening of the bond angles C7—C21—C26 (124.05I(17) ° for molecule A and 122.60 (18) ° for molecule B).

The structure features weak intra-molecular O—H···N, C—H···O interactions. The crystal structure features inter-molecular C—H···O and O—H···O interactions. The O1B—H1B···O3B interaction forms, inversely related dimers generating a graph set motif R22(12). These dimers are further interconnected by C1A—H3···O3B and C1A—H2···Cg1 inter-molecular interactions (where Cg1 is the ring centroid of (C21A—C26A) as shown in Fig 2.

Related literature top

For the importance of pyrrolizine derivatives, see: Anderson & Corey (1977); Makoni & Sugden (1980); Barsoum & Nawar (2003); Abbas et al. (2010). For the importance of piperidines, see: Rubiralta et al. (1991); Pinder (1992); Michael (2001). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-3-[E-(4-chlorophenyl)methylidene]tetrahydro-2(1H)- pyridinone (1 mmol), ninhydrin (1 mmol) and proline (1 mmol) in methanol was refluxed for 3–4 h. After completion of the reaction as indicated by TLC the reaction mixture was poured into cold water. The solid precipitate obtained was filtered and dried. The product was purified by column chromatography using petroleum ether:ethylacetate mixture (90:10 V/V). Suitable crystals for the single-crystal-X-ray studies were obtained by recrystalizing the product from methanol. Yield: 57%, Melting point: 470–472 K.

Refinement top

H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å. Uiso = 1.2Ueq(C) for CH2 and CH groups and Uiso = 1.5Ueq(C) for CH3 group.

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. H-atoms are omitted for clarity.
[Figure 2] Fig. 2. Partial packing diagram.
10-(4-Chlorophenyl)-14a-hydroxy-12-methyl-8,9,9a,10,12,13,14,14a-octahydro-5H-10a,14-methanoindeno[2',1':4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione top
Crystal data top
C26H25ClN2O3F(000) = 1888
Mr = 448.93Dx = 1.358 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ynCell parameters from 2000 reflections
a = 13.5839 (4) Åθ = 2–31°
b = 11.3764 (4) ŵ = 0.21 mm1
c = 28.5382 (9) ÅT = 293 K
β = 95.120 (2)°Block, colourless
V = 4392.6 (2) Å30.21 × 0.19 × 0.18 mm
Z = 8
Data collection top
Bruker Kappa APEXII
diffractometer
10365 independent reflections
Radiation source: fine-focus sealed tube7088 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 0 pixels mm-1θmax = 27.8°, θmin = 1.4°
ω and ϕ scansh = 1717
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.967, Tmax = 0.974l = 3737
85408 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0445P)2 + 2.0326P]
where P = (Fo2 + 2Fc2)/3
10365 reflections(Δ/σ)max < 0.001
591 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C26H25ClN2O3V = 4392.6 (2) Å3
Mr = 448.93Z = 8
Monoclinic, P21/nMo Kα radiation
a = 13.5839 (4) ŵ = 0.21 mm1
b = 11.3764 (4) ÅT = 293 K
c = 28.5382 (9) Å0.21 × 0.19 × 0.18 mm
β = 95.120 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
10365 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7088 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.974Rint = 0.041
85408 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.33 e Å3
10365 reflectionsΔρmin = 0.38 e Å3
591 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ (F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F.2 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
H20.2541 (19)0.164 (2)0.3395 (10)0.088 (9)*
H30.353 (2)0.193 (3)0.3711 (10)0.106 (10)*
C1A0.2818 (2)0.2028 (2)0.37004 (10)0.0629 (6)
C2A0.27703 (14)0.38693 (18)0.41290 (7)0.0479 (5)
H40.34840.39380.41750.057*
H50.25500.34330.43920.057*
C3A0.23041 (14)0.51019 (17)0.41138 (6)0.0452 (4)
H3A0.24760.55440.44040.054*
C4A0.26576 (14)0.56995 (17)0.36915 (7)0.0453 (4)
C5A0.21563 (12)0.50383 (15)0.32732 (6)0.0357 (4)
C6A0.27022 (13)0.38621 (16)0.32724 (6)0.0402 (4)
H60.24750.34090.29960.048*
H70.34080.39910.32700.048*
C7A0.20490 (13)0.57492 (16)0.28073 (6)0.0394 (4)
H7A0.22400.65630.28820.047*
C8A0.09354 (13)0.57262 (16)0.26891 (6)0.0408 (4)
H8A0.07470.49800.25340.049*
C9A0.03576 (16)0.67175 (19)0.24399 (7)0.0549 (5)
H80.03020.66070.21010.066*
H90.06630.74730.25150.066*
C10A0.06550 (16)0.6621 (2)0.26367 (8)0.0598 (6)
H10A0.08700.73850.27390.072*
H10B0.11450.63210.23990.072*
C11A0.05198 (14)0.5771 (2)0.30546 (8)0.0545 (5)
H11A0.08430.60620.33210.065*
H11B0.07740.49960.29700.065*
C12A0.10984 (12)0.48544 (15)0.34328 (6)0.0350 (4)
C13A0.11777 (13)0.50876 (16)0.39756 (6)0.0408 (4)
C14A0.06538 (13)0.40713 (17)0.41807 (6)0.0433 (4)
C15A0.03857 (13)0.32319 (17)0.38446 (7)0.0427 (4)
C16A0.06537 (13)0.36182 (16)0.33787 (6)0.0391 (4)
C17A0.00229 (14)0.2168 (2)0.39665 (8)0.0562 (5)
H17A0.01960.16000.37400.067*
C18A0.01649 (16)0.1976 (2)0.44325 (9)0.0693 (7)
H18A0.04350.12680.45220.083*
C19A0.00885 (17)0.2822 (3)0.47666 (9)0.0704 (7)
H19A0.00220.26810.50790.084*
C20A0.05034 (15)0.3872 (2)0.46474 (7)0.0572 (6)
H20A0.06790.44350.48760.069*
C21A0.26993 (14)0.53118 (16)0.24432 (6)0.0412 (4)
C22A0.36564 (15)0.57387 (19)0.24535 (7)0.0514 (5)
H22A0.38630.63120.26730.062*
C23A0.43091 (16)0.5337 (2)0.21480 (8)0.0575 (5)
H23A0.49500.56310.21620.069*
C24A0.39997 (16)0.44914 (18)0.18209 (7)0.0521 (5)
C25A0.30554 (17)0.40619 (18)0.17947 (7)0.0531 (5)
H25A0.28480.35030.15690.064*
C26A0.24137 (15)0.44680 (17)0.21074 (7)0.0475 (5)
H26A0.17750.41680.20920.057*
N1A0.24939 (11)0.32397 (13)0.36954 (5)0.0406 (3)
N2A0.05550 (11)0.57556 (13)0.31548 (5)0.0398 (3)
O1A0.07674 (12)0.61834 (13)0.40907 (5)0.0595 (4)
H1A0.06880.65920.38540.089*
O2A0.04810 (11)0.31079 (12)0.30075 (5)0.0524 (3)
O3A0.32204 (12)0.65099 (15)0.36775 (6)0.0709 (5)
Cl10.48368 (5)0.39797 (6)0.14410 (2)0.07186 (18)
H10.253 (2)0.162 (2)0.3931 (10)0.087 (9)*
C1B0.8571 (3)0.2820 (3)0.19339 (9)0.0890 (9)
H100.86040.19770.19330.134*
H110.79120.30630.19840.134*
H120.90250.31230.21820.134*
C2B0.97308 (15)0.27523 (19)0.13400 (7)0.0541 (5)
H130.96720.19030.13380.065*
H141.02820.29640.15640.065*
C3B0.99339 (14)0.31785 (17)0.08498 (7)0.0484 (5)
H3B1.05410.28380.07460.058*
C4B0.99805 (14)0.44975 (18)0.08757 (7)0.0492 (5)
C5B0.89285 (13)0.48782 (16)0.09453 (6)0.0408 (4)
C6B0.87928 (16)0.45404 (18)0.14540 (7)0.0502 (5)
H150.93140.48850.16650.060*
H160.81620.48250.15420.060*
C7B0.86807 (14)0.61561 (17)0.07776 (7)0.0447 (4)
H7B0.92380.64430.06140.054*
C8B0.78183 (14)0.59519 (18)0.04095 (7)0.0478 (5)
H8B0.72100.58870.05680.057*
C9B0.76111 (19)0.6683 (2)0.00292 (8)0.0667 (6)
H170.82180.69830.01390.080*
H180.71770.73360.00250.080*
C10B0.7105 (2)0.5801 (3)0.03822 (9)0.0782 (8)
H10C0.64130.59980.04520.094*
H10D0.74230.58030.06730.094*
C11B0.72132 (17)0.4603 (2)0.01442 (8)0.0650 (6)
H11C0.66180.43850.00010.078*
H11D0.73690.39960.03650.078*
C12B0.83195 (13)0.40302 (16)0.06015 (6)0.0397 (4)
C13B0.90496 (14)0.30332 (17)0.04781 (7)0.0438 (4)
C14B0.84778 (16)0.19125 (18)0.05099 (7)0.0508 (5)
C15B0.75861 (16)0.2098 (2)0.06915 (7)0.0563 (5)
C16B0.74522 (14)0.3361 (2)0.07891 (7)0.0520 (5)
C17B0.6951 (2)0.1162 (3)0.07601 (9)0.0800 (8)
H17B0.63450.12910.08800.096*
C18B0.7238 (3)0.0049 (3)0.06471 (11)0.0975 (12)
H18B0.68280.05880.06940.117*
C19B0.8123 (3)0.0127 (2)0.04657 (11)0.0929 (11)
H19B0.83020.08880.03890.111*
C20B0.8760 (2)0.0783 (2)0.03926 (8)0.0689 (7)
H20B0.93610.06460.02690.083*
C21B0.84957 (14)0.70415 (16)0.11559 (7)0.0438 (4)
C22B0.91994 (14)0.78879 (18)0.12870 (8)0.0512 (5)
H22B0.97830.79050.11390.061*
C23B0.90558 (16)0.87092 (18)0.16324 (8)0.0551 (5)
H23B0.95400.92660.17180.066*
C24B0.81938 (15)0.86902 (17)0.18455 (7)0.0497 (5)
C25B0.74774 (15)0.78766 (19)0.17235 (7)0.0521 (5)
H25B0.68920.78740.18700.063*
C26B0.76323 (15)0.70569 (18)0.13799 (7)0.0503 (5)
H26B0.71450.65020.12970.060*
N1B0.88309 (13)0.32669 (15)0.14848 (6)0.0501 (4)
N2B0.80391 (11)0.48068 (15)0.02110 (5)0.0452 (4)
O1B0.93885 (12)0.31807 (14)0.00264 (5)0.0630 (4)
H1B0.91680.37960.00900.095*
O2B0.67501 (11)0.38274 (17)0.09432 (6)0.0745 (5)
O3B1.06801 (11)0.51295 (14)0.08489 (7)0.0746 (5)
Cl20.80170 (5)0.97008 (5)0.22885 (2)0.07313 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0832 (18)0.0509 (13)0.0561 (15)0.0182 (12)0.0141 (13)0.0135 (11)
C2A0.0424 (10)0.0617 (13)0.0384 (10)0.0052 (9)0.0028 (8)0.0062 (9)
C3A0.0483 (10)0.0522 (11)0.0334 (9)0.0043 (9)0.0057 (8)0.0070 (8)
C4A0.0429 (10)0.0458 (11)0.0458 (11)0.0044 (8)0.0038 (8)0.0032 (9)
C5A0.0365 (9)0.0366 (9)0.0337 (9)0.0017 (7)0.0016 (7)0.0008 (7)
C6A0.0375 (9)0.0453 (10)0.0383 (10)0.0047 (8)0.0056 (7)0.0055 (8)
C7A0.0474 (10)0.0330 (9)0.0375 (9)0.0033 (7)0.0025 (8)0.0024 (7)
C8A0.0479 (10)0.0388 (9)0.0350 (9)0.0001 (8)0.0002 (8)0.0009 (7)
C9A0.0659 (13)0.0500 (12)0.0469 (12)0.0064 (10)0.0058 (10)0.0101 (9)
C10A0.0591 (13)0.0643 (14)0.0535 (13)0.0189 (11)0.0098 (10)0.0037 (11)
C11A0.0427 (11)0.0656 (13)0.0545 (12)0.0108 (10)0.0006 (9)0.0048 (10)
C12A0.0370 (9)0.0366 (9)0.0307 (8)0.0031 (7)0.0003 (7)0.0004 (7)
C13A0.0458 (10)0.0422 (10)0.0340 (9)0.0070 (8)0.0015 (7)0.0031 (8)
C14A0.0375 (9)0.0547 (11)0.0382 (10)0.0101 (8)0.0053 (8)0.0048 (8)
C15A0.0340 (9)0.0488 (11)0.0457 (11)0.0022 (8)0.0050 (8)0.0059 (9)
C16A0.0356 (9)0.0420 (10)0.0391 (10)0.0017 (7)0.0000 (7)0.0008 (8)
C17A0.0430 (11)0.0598 (13)0.0659 (14)0.0051 (9)0.0045 (10)0.0123 (11)
C18A0.0473 (12)0.0860 (18)0.0755 (17)0.0070 (12)0.0106 (11)0.0359 (15)
C19A0.0529 (13)0.107 (2)0.0535 (14)0.0044 (13)0.0145 (11)0.0282 (14)
C20A0.0499 (11)0.0825 (16)0.0401 (11)0.0112 (11)0.0093 (9)0.0062 (11)
C21A0.0504 (11)0.0383 (9)0.0352 (9)0.0019 (8)0.0053 (8)0.0069 (8)
C22A0.0543 (12)0.0544 (12)0.0458 (11)0.0083 (10)0.0059 (9)0.0021 (9)
C23A0.0516 (12)0.0638 (14)0.0585 (13)0.0041 (10)0.0124 (10)0.0061 (11)
C24A0.0629 (13)0.0488 (11)0.0470 (11)0.0094 (10)0.0177 (10)0.0113 (9)
C25A0.0694 (14)0.0457 (11)0.0452 (11)0.0022 (10)0.0106 (10)0.0013 (9)
C26A0.0534 (11)0.0449 (11)0.0448 (11)0.0056 (9)0.0077 (9)0.0001 (9)
N1A0.0435 (8)0.0431 (8)0.0352 (8)0.0071 (7)0.0035 (6)0.0054 (7)
N2A0.0413 (8)0.0422 (8)0.0353 (8)0.0064 (6)0.0007 (6)0.0024 (6)
O1A0.0820 (10)0.0513 (8)0.0447 (8)0.0204 (8)0.0037 (8)0.0089 (7)
O2A0.0661 (9)0.0468 (8)0.0429 (8)0.0086 (7)0.0028 (6)0.0062 (6)
O3A0.0751 (11)0.0716 (11)0.0636 (10)0.0352 (9)0.0071 (8)0.0027 (8)
Cl10.0799 (4)0.0717 (4)0.0688 (4)0.0167 (3)0.0327 (3)0.0072 (3)
C1B0.136 (3)0.0754 (18)0.0601 (16)0.0138 (17)0.0306 (16)0.0153 (14)
C2B0.0559 (12)0.0466 (11)0.0577 (13)0.0071 (9)0.0065 (10)0.0009 (10)
C3B0.0371 (10)0.0468 (11)0.0621 (13)0.0059 (8)0.0082 (9)0.0007 (9)
C4B0.0369 (10)0.0491 (11)0.0609 (13)0.0008 (9)0.0005 (9)0.0003 (10)
C5B0.0365 (9)0.0420 (10)0.0436 (10)0.0026 (7)0.0018 (8)0.0028 (8)
C6B0.0578 (12)0.0506 (11)0.0409 (10)0.0053 (9)0.0031 (9)0.0067 (9)
C7B0.0409 (10)0.0455 (10)0.0480 (11)0.0061 (8)0.0052 (8)0.0006 (8)
C8B0.0455 (10)0.0547 (12)0.0435 (11)0.0130 (9)0.0049 (8)0.0028 (9)
C9B0.0735 (15)0.0728 (16)0.0533 (13)0.0269 (13)0.0033 (11)0.0065 (12)
C10B0.0857 (18)0.098 (2)0.0486 (13)0.0361 (15)0.0093 (12)0.0017 (13)
C11B0.0630 (14)0.0873 (17)0.0428 (12)0.0138 (12)0.0067 (10)0.0161 (12)
C12B0.0353 (9)0.0482 (10)0.0363 (9)0.0007 (8)0.0063 (7)0.0041 (8)
C13B0.0460 (10)0.0465 (11)0.0407 (10)0.0027 (8)0.0132 (8)0.0012 (8)
C14B0.0658 (13)0.0490 (12)0.0365 (10)0.0062 (10)0.0011 (9)0.0019 (9)
C15B0.0621 (13)0.0655 (14)0.0402 (11)0.0195 (11)0.0012 (9)0.0016 (10)
C16B0.0410 (10)0.0768 (15)0.0389 (10)0.0083 (10)0.0068 (8)0.0053 (10)
C17B0.0836 (18)0.097 (2)0.0556 (15)0.0411 (16)0.0118 (13)0.0175 (14)
C18B0.131 (3)0.076 (2)0.077 (2)0.053 (2)0.038 (2)0.0258 (16)
C19B0.146 (3)0.0473 (14)0.0761 (19)0.0202 (18)0.043 (2)0.0091 (13)
C20B0.0987 (19)0.0507 (13)0.0542 (14)0.0024 (13)0.0109 (13)0.0009 (11)
C21B0.0428 (10)0.0394 (10)0.0479 (11)0.0073 (8)0.0022 (8)0.0024 (8)
C22B0.0422 (10)0.0484 (11)0.0624 (13)0.0042 (9)0.0023 (9)0.0035 (10)
C23B0.0539 (12)0.0446 (11)0.0645 (14)0.0014 (9)0.0084 (10)0.0027 (10)
C24B0.0556 (12)0.0412 (10)0.0501 (12)0.0096 (9)0.0066 (9)0.0023 (9)
C25B0.0475 (11)0.0561 (12)0.0523 (12)0.0066 (9)0.0020 (9)0.0069 (10)
C26B0.0451 (11)0.0499 (11)0.0553 (12)0.0006 (9)0.0006 (9)0.0071 (9)
N1B0.0628 (10)0.0477 (9)0.0400 (9)0.0043 (8)0.0063 (8)0.0010 (7)
N2B0.0442 (9)0.0554 (10)0.0364 (8)0.0084 (7)0.0048 (7)0.0028 (7)
O1B0.0782 (10)0.0615 (10)0.0542 (9)0.0205 (8)0.0330 (8)0.0069 (7)
O2B0.0466 (8)0.1099 (14)0.0703 (11)0.0027 (9)0.0236 (8)0.0088 (10)
O3B0.0399 (8)0.0588 (10)0.1244 (16)0.0073 (7)0.0032 (9)0.0015 (10)
Cl20.0842 (4)0.0606 (4)0.0737 (4)0.0030 (3)0.0022 (3)0.0226 (3)
Geometric parameters (Å, º) top
C1A—N1A1.447 (3)C1B—N1B1.451 (3)
C1A—H21.02 (3)C1B—H100.9600
C1A—H30.96 (3)C1B—H110.9600
C1A—H10.92 (3)C1B—H120.9600
C2A—N1A1.450 (2)C2B—N1B1.448 (3)
C2A—C3A1.538 (3)C2B—C3B1.529 (3)
C2A—H40.9700C2B—H130.9700
C2A—H50.9700C2B—H140.9700
C3A—C4A1.500 (3)C3B—C4B1.503 (3)
C3A—C13A1.546 (3)C3B—C13B1.539 (3)
C3A—H3A0.9800C3B—H3B0.9800
C4A—O3A1.201 (2)C4B—O3B1.200 (2)
C4A—C5A1.520 (2)C4B—C5B1.523 (3)
C5A—C6A1.530 (2)C5B—C6B1.529 (3)
C5A—C7A1.552 (2)C5B—C7B1.558 (3)
C5A—C12A1.560 (2)C5B—C12B1.560 (3)
C6A—N1A1.449 (2)C6B—N1B1.452 (3)
C6A—H60.9700C6B—H150.9700
C6A—H70.9700C6B—H160.9700
C7A—C21A1.507 (3)C7B—C21B1.514 (3)
C7A—C8A1.520 (3)C7B—C8B1.520 (3)
C7A—H7A0.9800C7B—H7B0.9800
C8A—N2A1.469 (2)C8B—N2B1.462 (2)
C8A—C9A1.515 (3)C8B—C9B1.508 (3)
C8A—H8A0.9800C8B—H8B0.9800
C9A—C10A1.535 (3)C9B—C10B1.539 (4)
C9A—H80.9700C9B—H170.9700
C9A—H90.9700C9B—H180.9700
C10A—C11A1.534 (3)C10B—C11B1.524 (4)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—N2A1.462 (2)C11B—N2B1.462 (3)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—N2A1.456 (2)C12B—N2B1.446 (2)
C12A—C16A1.533 (2)C12B—C16B1.538 (3)
C12A—C13A1.566 (2)C12B—C13B1.567 (3)
C13A—O1A1.416 (2)C13B—O1B1.417 (2)
C13A—C14A1.503 (3)C13B—C14B1.500 (3)
C14A—C15A1.379 (3)C14B—C15B1.376 (3)
C14A—C20A1.384 (3)C14B—C20B1.391 (3)
C15A—C17A1.389 (3)C15B—C17B1.395 (3)
C15A—C16A1.476 (3)C15B—C16B1.478 (3)
C16A—O2A1.212 (2)C16B—O2B1.208 (2)
C17A—C18A1.378 (3)C17B—C18B1.373 (5)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.376 (4)C18B—C19B1.366 (5)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.377 (3)C19B—C20B1.377 (4)
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.386 (3)C21B—C22B1.385 (3)
C21A—C26A1.387 (3)C21B—C26B1.385 (3)
C22A—C23A1.376 (3)C22B—C23B1.385 (3)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.379 (3)C23B—C24B1.367 (3)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.368 (3)C24B—C25B1.365 (3)
C24A—Cl11.740 (2)C24B—Cl21.741 (2)
C25A—C26A1.382 (3)C25B—C26B1.383 (3)
C25A—H25A0.9300C25B—H25B0.9300
C26A—H26A0.9300C26B—H26B0.9300
O1A—H1A0.8200O1B—H1B0.8200
N1A—C1A—H2108.4 (15)N1B—C1B—H10109.5
N1A—C1A—H3114.2 (19)N1B—C1B—H11109.5
H2—C1A—H3106 (2)H10—C1B—H11109.5
N1A—C1A—H1109.7 (17)N1B—C1B—H12109.5
H2—C1A—H1104 (2)H10—C1B—H12109.5
H3—C1A—H1114 (2)H11—C1B—H12109.5
N1A—C2A—C3A110.60 (15)N1B—C2B—C3B111.03 (16)
N1A—C2A—H4109.5N1B—C2B—H13109.4
C3A—C2A—H4109.5C3B—C2B—H13109.4
N1A—C2A—H5109.5N1B—C2B—H14109.4
C3A—C2A—H5109.5C3B—C2B—H14109.4
H4—C2A—H5108.1H13—C2B—H14108.0
C4A—C3A—C2A105.99 (16)C4B—C3B—C2B106.37 (17)
C4A—C3A—C13A100.39 (15)C4B—C3B—C13B99.67 (15)
C2A—C3A—C13A113.17 (16)C2B—C3B—C13B113.77 (16)
C4A—C3A—H3A112.2C4B—C3B—H3B112.1
C2A—C3A—H3A112.2C2B—C3B—H3B112.1
C13A—C3A—H3A112.2C13B—C3B—H3B112.1
O3A—C4A—C3A128.70 (18)O3B—C4B—C3B128.70 (18)
O3A—C4A—C5A126.59 (18)O3B—C4B—C5B126.56 (19)
C3A—C4A—C5A104.70 (15)C3B—C4B—C5B104.74 (15)
C4A—C5A—C6A104.52 (14)C4B—C5B—C6B104.26 (15)
C4A—C5A—C7A114.60 (15)C4B—C5B—C7B113.88 (15)
C6A—C5A—C7A117.58 (14)C6B—C5B—C7B119.04 (15)
C4A—C5A—C12A101.36 (14)C4B—C5B—C12B101.13 (14)
C6A—C5A—C12A110.02 (14)C6B—C5B—C12B109.86 (15)
C7A—C5A—C12A107.55 (13)C7B—C5B—C12B107.22 (14)
N1A—C6A—C5A107.18 (14)N1B—C6B—C5B107.56 (15)
N1A—C6A—H6110.3N1B—C6B—H15110.2
C5A—C6A—H6110.3C5B—C6B—H15110.2
N1A—C6A—H7110.3N1B—C6B—H16110.2
C5A—C6A—H7110.3C5B—C6B—H16110.2
H6—C6A—H7108.5H15—C6B—H16108.5
C21A—C7A—C8A118.30 (15)C21B—C7B—C8B115.33 (15)
C21A—C7A—C5A113.74 (15)C21B—C7B—C5B116.54 (16)
C8A—C7A—C5A101.33 (14)C8B—C7B—C5B101.64 (15)
C21A—C7A—H7A107.6C21B—C7B—H7B107.6
C8A—C7A—H7A107.6C8B—C7B—H7B107.6
C5A—C7A—H7A107.6C5B—C7B—H7B107.6
N2A—C8A—C9A101.46 (15)N2B—C8B—C9B101.49 (16)
N2A—C8A—C7A102.85 (14)N2B—C8B—C7B103.40 (15)
C9A—C8A—C7A123.70 (16)C9B—C8B—C7B124.37 (19)
N2A—C8A—H8A109.2N2B—C8B—H8B108.8
C9A—C8A—H8A109.2C9B—C8B—H8B108.8
C7A—C8A—H8A109.2C7B—C8B—H8B108.8
C8A—C9A—C10A102.64 (16)C8B—C9B—C10B102.9 (2)
C8A—C9A—H8111.2C8B—C9B—H17111.2
C10A—C9A—H8111.2C10B—C9B—H17111.2
C8A—C9A—H9111.2C8B—C9B—H18111.2
C10A—C9A—H9111.2C10B—C9B—H18111.2
H8—C9A—H9109.2H17—C9B—H18109.1
C11A—C10A—C9A106.28 (16)C11B—C10B—C9B105.76 (18)
C11A—C10A—H10A110.5C11B—C10B—H10C110.6
C9A—C10A—H10A110.5C9B—C10B—H10C110.6
C11A—C10A—H10B110.5C11B—C10B—H10D110.6
C9A—C10A—H10B110.5C9B—C10B—H10D110.6
H10A—C10A—H10B108.7H10C—C10B—H10D108.7
N2A—C11A—C10A102.00 (17)N2B—C11B—C10B101.8 (2)
N2A—C11A—H11A111.4N2B—C11B—H11C111.4
C10A—C11A—H11A111.4C10B—C11B—H11C111.4
N2A—C11A—H11B111.4N2B—C11B—H11D111.4
C10A—C11A—H11B111.4C10B—C11B—H11D111.4
H11A—C11A—H11B109.2H11C—C11B—H11D109.3
N2A—C12A—C16A114.52 (14)N2B—C12B—C16B114.40 (15)
N2A—C12A—C5A100.48 (13)N2B—C12B—C5B101.26 (14)
C16A—C12A—C5A117.31 (14)C16B—C12B—C5B117.83 (15)
N2A—C12A—C13A113.98 (14)N2B—C12B—C13B113.41 (14)
C16A—C12A—C13A104.28 (14)C16B—C12B—C13B103.87 (16)
C5A—C12A—C13A106.40 (13)C5B—C12B—C13B106.16 (14)
O1A—C13A—C14A112.15 (15)O1B—C13B—C14B111.57 (16)
O1A—C13A—C3A109.43 (16)O1B—C13B—C3B108.50 (16)
C14A—C13A—C3A113.63 (15)C14B—C13B—C3B115.23 (16)
O1A—C13A—C12A112.64 (14)O1B—C13B—C12B112.47 (15)
C14A—C13A—C12A105.17 (14)C14B—C13B—C12B105.08 (15)
C3A—C13A—C12A103.49 (14)C3B—C13B—C12B103.77 (15)
C15A—C14A—C20A120.2 (2)C15B—C14B—C20B120.2 (2)
C15A—C14A—C13A111.51 (16)C15B—C14B—C13B111.76 (18)
C20A—C14A—C13A128.05 (19)C20B—C14B—C13B128.0 (2)
C14A—C15A—C17A121.06 (19)C14B—C15B—C17B120.9 (2)
C14A—C15A—C16A110.43 (16)C14B—C15B—C16B110.32 (18)
C17A—C15A—C16A128.41 (19)C17B—C15B—C16B128.8 (2)
O2A—C16A—C15A126.89 (17)O2B—C16B—C15B127.6 (2)
O2A—C16A—C12A124.82 (17)O2B—C16B—C12B124.3 (2)
C15A—C16A—C12A108.00 (15)C15B—C16B—C12B107.73 (17)
C18A—C17A—C15A118.2 (2)C18B—C17B—C15B118.6 (3)
C18A—C17A—H17A120.9C18B—C17B—H17B120.7
C15A—C17A—H17A120.9C15B—C17B—H17B120.7
C19A—C18A—C17A120.7 (2)C19B—C18B—C17B120.2 (3)
C19A—C18A—H18A119.7C19B—C18B—H18B119.9
C17A—C18A—H18A119.7C17B—C18B—H18B119.9
C18A—C19A—C20A121.2 (2)C18B—C19B—C20B122.3 (3)
C18A—C19A—H19A119.4C18B—C19B—H19B118.9
C20A—C19A—H19A119.4C20B—C19B—H19B118.9
C19A—C20A—C14A118.6 (2)C19B—C20B—C14B117.9 (3)
C19A—C20A—H20A120.7C19B—C20B—H20B121.1
C14A—C20A—H20A120.7C14B—C20B—H20B121.1
C22A—C21A—C26A117.46 (18)C22B—C21B—C26B117.33 (18)
C22A—C21A—C7A118.44 (17)C22B—C21B—C7B120.06 (18)
C26A—C21A—C7A124.05 (17)C26B—C21B—C7B122.60 (18)
C23A—C22A—C21A121.8 (2)C21B—C22B—C23B121.60 (19)
C23A—C22A—H22A119.1C21B—C22B—H22B119.2
C21A—C22A—H22A119.1C23B—C22B—H22B119.2
C22A—C23A—C24A119.1 (2)C24B—C23B—C22B119.13 (19)
C22A—C23A—H23A120.5C24B—C23B—H23B120.4
C24A—C23A—H23A120.5C22B—C23B—H23B120.4
C25A—C24A—C23A120.89 (19)C25B—C24B—C23B121.11 (19)
C25A—C24A—Cl1120.53 (17)C25B—C24B—Cl2119.43 (17)
C23A—C24A—Cl1118.58 (17)C23B—C24B—Cl2119.45 (16)
C24A—C25A—C26A119.2 (2)C24B—C25B—C26B119.2 (2)
C24A—C25A—H25A120.4C24B—C25B—H25B120.4
C26A—C25A—H25A120.4C26B—C25B—H25B120.4
C25A—C26A—C21A121.61 (19)C25B—C26B—C21B121.63 (19)
C25A—C26A—H26A119.2C25B—C26B—H26B119.2
C21A—C26A—H26A119.2C21B—C26B—H26B119.2
C1A—N1A—C6A113.07 (16)C2B—N1B—C1B112.85 (19)
C1A—N1A—C2A114.00 (17)C2B—N1B—C6B114.35 (17)
C6A—N1A—C2A114.49 (15)C1B—N1B—C6B113.15 (18)
C12A—N2A—C11A124.31 (15)C12B—N2B—C11B124.78 (17)
C12A—N2A—C8A105.94 (13)C12B—N2B—C8B107.15 (14)
C11A—N2A—C8A104.43 (14)C11B—N2B—C8B103.81 (15)
C13A—O1A—H1A109.5C13B—O1B—H1B109.5
N1A—C2A—C3A—C4A57.63 (19)N1B—C2B—C3B—C4B57.2 (2)
N1A—C2A—C3A—C13A51.4 (2)N1B—C2B—C3B—C13B51.5 (2)
C2A—C3A—C4A—O3A110.9 (2)C2B—C3B—C4B—O3B112.0 (3)
C13A—C3A—C4A—O3A131.2 (2)C13B—C3B—C4B—O3B129.5 (2)
C2A—C3A—C4A—C5A68.25 (17)C2B—C3B—C4B—C5B67.91 (19)
C13A—C3A—C4A—C5A49.70 (18)C13B—C3B—C4B—C5B50.53 (18)
O3A—C4A—C5A—C6A105.8 (2)O3B—C4B—C5B—C6B107.0 (2)
C3A—C4A—C5A—C6A73.31 (17)C3B—C4B—C5B—C6B72.93 (19)
O3A—C4A—C5A—C7A24.3 (3)O3B—C4B—C5B—C7B24.3 (3)
C3A—C4A—C5A—C7A156.55 (15)C3B—C4B—C5B—C7B155.75 (16)
O3A—C4A—C5A—C12A139.8 (2)O3B—C4B—C5B—C12B139.0 (2)
C3A—C4A—C5A—C12A41.07 (17)C3B—C4B—C5B—C12B41.10 (19)
C4A—C5A—C6A—N1A65.78 (17)C4B—C5B—C6B—N1B65.79 (19)
C7A—C5A—C6A—N1A165.87 (14)C7B—C5B—C6B—N1B165.98 (16)
C12A—C5A—C6A—N1A42.34 (18)C12B—C5B—C6B—N1B41.9 (2)
C4A—C5A—C7A—C21A110.27 (18)C4B—C5B—C7B—C21B112.93 (19)
C6A—C5A—C7A—C21A13.1 (2)C6B—C5B—C7B—C21B10.7 (2)
C12A—C5A—C7A—C21A137.89 (15)C12B—C5B—C7B—C21B136.07 (16)
C4A—C5A—C7A—C8A121.68 (16)C4B—C5B—C7B—C8B120.83 (17)
C6A—C5A—C7A—C8A114.94 (16)C6B—C5B—C7B—C8B115.54 (18)
C12A—C5A—C7A—C8A9.84 (17)C12B—C5B—C7B—C8B9.83 (18)
C21A—C7A—C8A—N2A158.96 (15)C21B—C7B—C8B—N2B159.34 (16)
C5A—C7A—C8A—N2A33.91 (16)C5B—C7B—C8B—N2B32.31 (18)
C21A—C7A—C8A—C9A87.6 (2)C21B—C7B—C8B—C9B86.4 (2)
C5A—C7A—C8A—C9A147.30 (17)C5B—C7B—C8B—C9B146.57 (19)
N2A—C8A—C9A—C10A36.18 (19)N2B—C8B—C9B—C10B34.9 (2)
C7A—C8A—C9A—C10A150.26 (18)C7B—C8B—C9B—C10B150.1 (2)
C8A—C9A—C10A—C11A11.7 (2)C8B—C9B—C10B—C11B8.9 (2)
C9A—C10A—C11A—N2A17.2 (2)C9B—C10B—C11B—N2B20.4 (2)
C4A—C5A—C12A—N2A102.79 (14)C4B—C5B—C12B—N2B103.29 (15)
C6A—C5A—C12A—N2A147.00 (14)C6B—C5B—C12B—N2B146.95 (14)
C7A—C5A—C12A—N2A17.79 (16)C7B—C5B—C12B—N2B16.24 (17)
C4A—C5A—C12A—C16A132.43 (15)C4B—C5B—C12B—C16B131.17 (18)
C6A—C5A—C12A—C16A22.2 (2)C6B—C5B—C12B—C16B21.4 (2)
C7A—C5A—C12A—C16A106.99 (16)C7B—C5B—C12B—C16B109.30 (19)
C4A—C5A—C12A—C13A16.24 (17)C4B—C5B—C12B—C13B15.37 (18)
C6A—C5A—C12A—C13A93.97 (16)C6B—C5B—C12B—C13B94.39 (17)
C7A—C5A—C12A—C13A136.82 (14)C7B—C5B—C12B—C13B134.90 (15)
C4A—C3A—C13A—O1A83.08 (17)C4B—C3B—C13B—O1B81.23 (18)
C2A—C3A—C13A—O1A164.40 (15)C2B—C3B—C13B—O1B165.97 (16)
C4A—C3A—C13A—C14A150.71 (16)C4B—C3B—C13B—C14B152.87 (17)
C2A—C3A—C13A—C14A38.2 (2)C2B—C3B—C13B—C14B40.1 (2)
C4A—C3A—C13A—C12A37.21 (17)C4B—C3B—C13B—C12B38.57 (18)
C2A—C3A—C13A—C12A75.31 (18)C2B—C3B—C13B—C12B74.23 (19)
N2A—C12A—C13A—O1A4.5 (2)N2B—C12B—C13B—O1B7.6 (2)
C16A—C12A—C13A—O1A130.12 (16)C16B—C12B—C13B—O1B132.37 (17)
C5A—C12A—C13A—O1A105.25 (17)C5B—C12B—C13B—O1B102.72 (18)
N2A—C12A—C13A—C14A117.90 (16)N2B—C12B—C13B—C14B113.99 (17)
C16A—C12A—C13A—C14A7.68 (17)C16B—C12B—C13B—C14B10.80 (18)
C5A—C12A—C13A—C14A132.32 (14)C5B—C12B—C13B—C14B135.71 (15)
N2A—C12A—C13A—C3A122.62 (15)N2B—C12B—C13B—C3B124.64 (16)
C16A—C12A—C13A—C3A111.80 (15)C16B—C12B—C13B—C3B110.56 (16)
C5A—C12A—C13A—C3A12.83 (17)C5B—C12B—C13B—C3B14.34 (18)
O1A—C13A—C14A—C15A129.46 (17)O1B—C13B—C14B—C15B130.14 (18)
C3A—C13A—C14A—C15A105.78 (18)C3B—C13B—C14B—C15B105.6 (2)
C12A—C13A—C14A—C15A6.71 (19)C12B—C13B—C14B—C15B8.0 (2)
O1A—C13A—C14A—C20A56.2 (2)O1B—C13B—C14B—C20B51.6 (3)
C3A—C13A—C14A—C20A68.6 (2)C3B—C13B—C14B—C20B72.7 (3)
C12A—C13A—C14A—C20A178.91 (18)C12B—C13B—C14B—C20B173.8 (2)
C20A—C14A—C15A—C17A1.1 (3)C20B—C14B—C15B—C17B0.1 (3)
C13A—C14A—C15A—C17A173.81 (17)C13B—C14B—C15B—C17B178.52 (19)
C20A—C14A—C15A—C16A177.66 (17)C20B—C14B—C15B—C16B179.84 (19)
C13A—C14A—C15A—C16A2.8 (2)C13B—C14B—C15B—C16B1.5 (2)
C14A—C15A—C16A—O2A176.55 (18)C14B—C15B—C16B—O2B178.9 (2)
C17A—C15A—C16A—O2A7.2 (3)C17B—C15B—C16B—O2B1.1 (4)
C14A—C15A—C16A—C12A2.5 (2)C14B—C15B—C16B—C12B5.9 (2)
C17A—C15A—C16A—C12A178.77 (18)C17B—C15B—C16B—C12B174.1 (2)
N2A—C12A—C16A—O2A55.3 (2)N2B—C12B—C16B—O2B59.4 (3)
C5A—C12A—C16A—O2A62.1 (2)C5B—C12B—C16B—O2B59.4 (3)
C13A—C12A—C16A—O2A179.44 (17)C13B—C12B—C16B—O2B176.43 (19)
N2A—C12A—C16A—C15A118.90 (16)N2B—C12B—C16B—C15B113.88 (18)
C5A—C12A—C16A—C15A123.68 (16)C5B—C12B—C16B—C15B127.31 (17)
C13A—C12A—C16A—C15A6.34 (17)C13B—C12B—C16B—C15B10.3 (2)
C14A—C15A—C17A—C18A0.7 (3)C14B—C15B—C17B—C18B0.6 (3)
C16A—C15A—C17A—C18A176.67 (19)C16B—C15B—C17B—C18B179.3 (2)
C15A—C17A—C18A—C19A0.3 (3)C15B—C17B—C18B—C19B0.8 (4)
C17A—C18A—C19A—C20A1.0 (4)C17B—C18B—C19B—C20B0.5 (4)
C18A—C19A—C20A—C14A0.7 (3)C18B—C19B—C20B—C14B0.0 (4)
C15A—C14A—C20A—C19A0.4 (3)C15B—C14B—C20B—C19B0.2 (3)
C13A—C14A—C20A—C19A173.59 (19)C13B—C14B—C20B—C19B177.9 (2)
C8A—C7A—C21A—C22A154.36 (17)C8B—C7B—C21B—C22B134.64 (19)
C5A—C7A—C21A—C22A86.9 (2)C5B—C7B—C21B—C22B106.3 (2)
C8A—C7A—C21A—C26A28.4 (3)C8B—C7B—C21B—C26B44.6 (3)
C5A—C7A—C21A—C26A90.4 (2)C5B—C7B—C21B—C26B74.4 (2)
C26A—C21A—C22A—C23A0.8 (3)C26B—C21B—C22B—C23B0.9 (3)
C7A—C21A—C22A—C23A176.65 (19)C7B—C21B—C22B—C23B179.83 (18)
C21A—C22A—C23A—C24A0.4 (3)C21B—C22B—C23B—C24B0.7 (3)
C22A—C23A—C24A—C25A0.7 (3)C22B—C23B—C24B—C25B0.1 (3)
C22A—C23A—C24A—Cl1179.32 (16)C22B—C23B—C24B—Cl2178.72 (16)
C23A—C24A—C25A—C26A1.3 (3)C23B—C24B—C25B—C26B0.3 (3)
Cl1—C24A—C25A—C26A178.69 (15)Cl2—C24B—C25B—C26B178.36 (16)
C24A—C25A—C26A—C21A0.9 (3)C24B—C25B—C26B—C21B0.1 (3)
C22A—C21A—C26A—C25A0.2 (3)C22B—C21B—C26B—C25B0.5 (3)
C7A—C21A—C26A—C25A177.14 (18)C7B—C21B—C26B—C25B179.77 (18)
C5A—C6A—N1A—C1A169.67 (19)C3B—C2B—N1B—C1B175.8 (2)
C5A—C6A—N1A—C2A57.50 (19)C3B—C2B—N1B—C6B53.0 (2)
C3A—C2A—N1A—C1A173.92 (19)C5B—C6B—N1B—C2B57.2 (2)
C3A—C2A—N1A—C6A53.7 (2)C5B—C6B—N1B—C1B171.7 (2)
C16A—C12A—N2A—C11A34.4 (2)C16B—C12B—N2B—C11B31.6 (2)
C5A—C12A—N2A—C11A161.08 (17)C5B—C12B—N2B—C11B159.41 (17)
C13A—C12A—N2A—C11A85.6 (2)C13B—C12B—N2B—C11B87.3 (2)
C16A—C12A—N2A—C8A86.16 (17)C16B—C12B—N2B—C8B89.63 (19)
C5A—C12A—N2A—C8A40.51 (16)C5B—C12B—N2B—C8B38.18 (17)
C13A—C12A—N2A—C8A153.87 (15)C13B—C12B—N2B—C8B151.47 (15)
C10A—C11A—N2A—C12A162.38 (16)C10B—C11B—N2B—C12B166.35 (17)
C10A—C11A—N2A—C8A41.11 (19)C10B—C11B—N2B—C8B43.6 (2)
C9A—C8A—N2A—C12A177.77 (14)C9B—C8B—N2B—C12B176.22 (16)
C7A—C8A—N2A—C12A48.94 (17)C7B—C8B—N2B—C12B46.38 (19)
C9A—C8A—N2A—C11A49.47 (18)C9B—C8B—N2B—C11B50.1 (2)
C7A—C8A—N2A—C11A178.30 (15)C7B—C8B—N2B—C11B179.94 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C21A–C26A ring.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N2A0.822.202.705 (2)120
O1B—H1B···N2B0.822.162.689 (2)123
C8A—H8A···O2A0.982.573.190 (2)122
O1B—H1B···O3Bi0.822.513.147 (2)135
C1A—H3···O3Bii0.96 (3)2.59 (3)3.164 (3)118 (2)
C1A—H2···Cg1iii1.02 (3)2.70 (3)3.648 (3)155 (2)
Symmetry codes: (i) x+2, y+1, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C21A–C26A ring.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N2A0.822.202.705 (2)119.7
O1B—H1B···N2B0.822.162.689 (2)122.7
C8A—H8A···O2A0.982.573.190 (2)121.6
O1B—H1B···O3Bi0.822.513.147 (2)135.2
C1A—H3···O3Bii0.96 (3)2.59 (3)3.164 (3)118 (2)
C1A—H2···Cg1iii1.02 (3)2.70 (3)3.648 (3)155 (2)
Symmetry codes: (i) x+2, y+1, z; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2.
 

Acknowledgements

JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).

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Volume 70| Part 1| January 2014| Pages o97-o98
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