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

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ISSN: 2056-9890

(1R*,3′S*,4′R*)-4′-(4-Chloro­phen­yl)-3′-[(4-hy­dr­oxy-2-oxo-1,2-di­hydro­quinolin-3-yl)carbon­yl]-1′-methyl­spiro­[ace­naphthyl­ene-1,2′-pyrrolidin]-2-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bSchool of Chemical Sciences, Bharathiar University, Coimbatore 641 046, India
*Correspondence e-mail: shirai2011@gmail.com

(Received 28 September 2011; accepted 16 November 2011; online 19 November 2011)

The title compound, C32H23ClN2O4, has a quinoline, a chloro­phenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two mol­ecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intra­molecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R22(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å3) within which there is no evidence of solvent mol­ecules.

Related literature

For the synthesis of the title compound, see: Suresh Babu et al. (2006[Suresh Babu, A. R., Raghunathan, R., Gayatri, G. & Narahari Sastry, G. (2006). J. Heterocycl. Chem. 43, 1467-1472.]); Amal Raj & Raghunathan (2003)[Amal Raj, A. & Raghunathan, R. (2003). Tetrahedron, 59, 2907-2911.]; Ponnusamy et al. (2007[Ponnusamy, S., Baby, V. & Suchithra, M. (2007). Org. Lett. 21, 4095-4098.]). For related structures, see: Thenmozhi et al. (2011[Thenmozhi, S., Govindan, E., Gavaskar, D., Raghunathan, R. & SubbiahPandi, A. (2011). Acta Cryst. E67, o268.]); Augustine et al. (2010[Augustine, T., Vithiya, S. M., Ignacimuthu, S. & Ramkumar, V. (2010). Acta Cryst. E66, o3002.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For asymmetry analysis, see: Nardelli et al. (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C32H23ClN2O4

  • Mr = 534.97

  • Triclinic, [P \overline 1]

  • a = 10.7447 (7) Å

  • b = 14.1678 (9) Å

  • c = 18.3858 (11) Å

  • α = 101.328 (3)°

  • β = 91.945 (3)°

  • γ = 105.388 (3)°

  • V = 2635.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 293 K

  • 0.25 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.961

  • 47617 measured reflections

  • 13107 independent reflections

  • 6910 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.151

  • S = 0.94

  • 13107 reflections

  • 705 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.86 2.03 2.879 (2) 171
O1—H1B⋯O3 0.82 1.74 2.468 (2) 147
N1A—H1A⋯O2Aii 0.86 2.01 2.865 (2) 174
O1A—H1′⋯O3A 0.82 1.75 2.477 (2) 148
C3A—H3A⋯O4iii 0.93 2.45 3.245 (3) 143
C30A—H30A⋯O2iv 0.93 2.54 3.413 (2) 157
Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x+2, -y+2, -z+1; (iii) -x+1, -y+2, -z+1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

X-ray analysis confirms the molecular structure and atom connectivity of the title compound as shown in Figure 1. The pyrrolidine ring system makes dihedral angles of 90.93 (6), 94.08 (6) and 91.15 (6) ° with quinoline, acenaphthalene and chlorophenyl rings, respectively. The refined structure was observed with total potential solvent area volume of 60 Å3 although no solvent molecule can be detected therein.

The five membered pyrrolidine ring (C11-C13, N2, C14) adopts an envelope conformation with a two fold symmtery axis passing through C13, with the puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ (Nardelli et al., 1983), as follows: q2= 0.64 (3) Å, φ = 154.8 (2)°, Δs(C13) = 0.504 (2)°. The same ring is slightly twisted with regard to the N2A-C13A bond in the second molecule in the asymmetric unit. The puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ (Nardelli et al., 1983) of the pyrrolidine ring in the second molecule are q2= 0.67 (3) Å, φ = 151.5 (2)°, Δs(N2A) = 0.067 (1) and Δs(C13A) = 0.074 (1). The sum of angles at N2 of the pyrrolidine ring (340°) is in accordance with sp3 hybridization. A weak C32-H32F···cg17 interaction with a distance of 3.545 (3) Å is also observed (cg17 is the centroid of the C16, C17, C22-C25 ring).

Hydrogen bonds (Table 1) forming a R22(8) motif link symmetry related molecule as dimers (shown with dotted lines in Figure 2).

Related literature top

For the synthesis of the title compound, see: Suresh Babu et al. (2006); Amal Raj & Raghunathan (2003); Ponnusamy et al. (2007). For related structures, see: Thenmozhi et al. (2011); Augustine et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For asymmetry analysis, see: Nardelli et al. (1983).

Experimental top

A mixture of (E)-3-(3-(4-chlorophenyl)acryloyl)-4-hydroxyquinolin-2(1H)-one (0.5 mmol) , acenaphthene quinone (0.5 mmol) and sarcosine (0.55 mmol) was refluxed in methanol until the disappearance of the starting materials as evidenced by TLC. After completion of the reaction, the solvent was removed in vacuo and the residue was chromatographed on silica gel using hexane-ethylacetate mixture (7:2) as eluent to give the title compound (yield: 58%). The compound was recrystallised from a DMF-methanol mixture (2:8 v/v).

Refinement top

H-atoms were positioned geometrically and treated as riding atoms: C—H =0.93 Å H-aromatic, C—H = 0.96 Å H-methyl, and N—H = 0.86 Å, with Uiso = k×Ueq(parent C or N-atom), where k = 1.5 for methyl H-atoms, and = 1.2 for all other H-atoms.

Structure description top

X-ray analysis confirms the molecular structure and atom connectivity of the title compound as shown in Figure 1. The pyrrolidine ring system makes dihedral angles of 90.93 (6), 94.08 (6) and 91.15 (6) ° with quinoline, acenaphthalene and chlorophenyl rings, respectively. The refined structure was observed with total potential solvent area volume of 60 Å3 although no solvent molecule can be detected therein.

The five membered pyrrolidine ring (C11-C13, N2, C14) adopts an envelope conformation with a two fold symmtery axis passing through C13, with the puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ (Nardelli et al., 1983), as follows: q2= 0.64 (3) Å, φ = 154.8 (2)°, Δs(C13) = 0.504 (2)°. The same ring is slightly twisted with regard to the N2A-C13A bond in the second molecule in the asymmetric unit. The puckering parameters q2 and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ (Nardelli et al., 1983) of the pyrrolidine ring in the second molecule are q2= 0.67 (3) Å, φ = 151.5 (2)°, Δs(N2A) = 0.067 (1) and Δs(C13A) = 0.074 (1). The sum of angles at N2 of the pyrrolidine ring (340°) is in accordance with sp3 hybridization. A weak C32-H32F···cg17 interaction with a distance of 3.545 (3) Å is also observed (cg17 is the centroid of the C16, C17, C22-C25 ring).

Hydrogen bonds (Table 1) forming a R22(8) motif link symmetry related molecule as dimers (shown with dotted lines in Figure 2).

For the synthesis of the title compound, see: Suresh Babu et al. (2006); Amal Raj & Raghunathan (2003); Ponnusamy et al. (2007). For related structures, see: Thenmozhi et al. (2011); Augustine et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For asymmetry analysis, see: Nardelli et al. (1983).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title molecule showing thermal ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. View of the motifs with hydrogen bonds (dotted lines) formed between the molecules.
(1R*,3'S*,4'R*)-4'-(4-Chlorophenyl)-3'-[(4-hydroxy-2-oxo- 1,2-dihydroquinolin-3-yl)carbonyl]-1'-methylspiro[acenaphthylene-1,2'- pyrrolidin]-2-one top
Crystal data top
C32H23ClN2O4V = 2635.0 (3) Å3
Mr = 534.97Z = 4
Triclinic, P1F(000) = 1112
Hall symbol: -P 1Dx = 1.349 Mg m3
a = 10.7447 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.1678 (9) Åθ = 1.1–28.4°
c = 18.3858 (11) ŵ = 0.19 mm1
α = 101.328 (3)°T = 293 K
β = 91.945 (3)°Block, colorless
γ = 105.388 (3)°0.25 × 0.24 × 0.21 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
13107 independent reflections
Radiation source: fine-focus sealed tube6910 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and φ scansθmax = 28.4°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1414
Tmin = 0.954, Tmax = 0.961k = 1818
47617 measured reflectionsl = 2424
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.5485P]
where P = (Fo2 + 2Fc2)/3
13107 reflections(Δ/σ)max = 0.001
705 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C32H23ClN2O4γ = 105.388 (3)°
Mr = 534.97V = 2635.0 (3) Å3
Triclinic, P1Z = 4
a = 10.7447 (7) ÅMo Kα radiation
b = 14.1678 (9) ŵ = 0.19 mm1
c = 18.3858 (11) ÅT = 293 K
α = 101.328 (3)°0.25 × 0.24 × 0.21 mm
β = 91.945 (3)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
13107 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
6910 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.961Rint = 0.029
47617 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 0.94Δρmax = 0.34 e Å3
13107 reflectionsΔρmin = 0.42 e Å3
705 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C32A0.6670 (3)0.5141 (2)0.49180 (15)0.0904 (7)
H32A0.60270.54190.47380.136*
H32B0.68590.53900.54460.136*
H32C0.63460.44240.48140.136*
C320.3307 (3)1.03417 (17)0.05072 (15)0.0930 (8)
H32D0.38041.01820.09130.139*
H32E0.38831.02500.00720.139*
H32F0.27891.10260.06390.139*
Cl10.94664 (7)0.60486 (5)0.03472 (3)0.0873 (2)
O2A0.98837 (13)0.87799 (9)0.44141 (7)0.0621 (3)
N1A1.13187 (16)0.96189 (11)0.53970 (9)0.0581 (4)
H1A1.09841.01110.54230.070*
C26A0.90685 (19)0.56594 (14)0.27100 (11)0.0559 (5)
C9A1.08106 (18)0.87937 (14)0.48428 (10)0.0521 (4)
C5A1.2322 (2)0.97268 (15)0.59168 (11)0.0604 (5)
C8A1.14086 (18)0.79780 (14)0.47957 (10)0.0557 (5)
O1A1.31369 (16)0.74260 (13)0.52380 (11)0.1010 (6)
H1'1.27710.69360.49110.151*
C12A0.89913 (19)0.55895 (14)0.35147 (11)0.0567 (5)
H12A0.95880.52120.36300.068*
C17A0.8743 (2)0.76707 (15)0.58762 (12)0.0643 (5)
C11A0.93974 (18)0.66263 (13)0.40624 (10)0.0523 (4)
H11A0.91960.71240.38110.063*
N2A0.78450 (17)0.54291 (12)0.45484 (9)0.0647 (4)
O3A1.14633 (15)0.63588 (11)0.42387 (9)0.0781 (4)
C1OA1.08172 (19)0.69753 (15)0.43389 (10)0.0568 (5)
C18A0.9147 (2)0.68525 (15)0.55090 (11)0.0612 (5)
C29A0.9307 (2)0.58683 (15)0.12507 (11)0.0632 (5)
C30A0.8217 (2)0.59724 (16)0.15805 (11)0.0657 (5)
H30A0.75550.61090.13160.079*
C16A0.7811 (2)0.78996 (16)0.54437 (13)0.0677 (6)
C6A1.2965 (2)0.89865 (16)0.58606 (12)0.0670 (5)
O4A0.68516 (16)0.71479 (13)0.41899 (10)0.0881 (5)
C7A1.2507 (2)0.81183 (16)0.52715 (13)0.0675 (6)
C14A0.85067 (19)0.65057 (14)0.47205 (11)0.0567 (5)
C31A0.8106 (2)0.58739 (16)0.23095 (11)0.0644 (5)
H31A0.73680.59540.25350.077*
C28A1.0268 (2)0.56482 (17)0.16250 (13)0.0740 (6)
H28A1.10040.55740.13950.089*
C13A0.7675 (2)0.50945 (15)0.37431 (11)0.0666 (5)
H13A0.69980.53190.35270.080*
H13B0.74670.43700.35970.080*
C21A1.0150 (3)0.7865 (2)0.69607 (13)0.0876 (8)
H21A1.05190.82020.74370.105*
C22A0.9232 (3)0.82072 (17)0.66006 (13)0.0769 (7)
C4A1.2686 (2)1.05653 (17)0.65045 (13)0.0787 (6)
H4A1.22711.10690.65380.094*
C19A1.0008 (2)0.65235 (18)0.58867 (12)0.0748 (6)
H19A1.02640.59640.56660.090*
C15A0.7589 (2)0.71995 (16)0.47137 (13)0.0652 (5)
C27A1.0143 (2)0.55366 (17)0.23487 (13)0.0702 (6)
H27A1.07960.53750.26010.084*
C1A1.3969 (2)0.9090 (2)0.64031 (16)0.0923 (8)
H1A21.44130.86040.63680.111*
C20A1.0499 (3)0.7049 (2)0.66176 (14)0.0872 (7)
H20A1.10860.68250.68750.105*
C3A1.3662 (3)1.0638 (2)0.70312 (15)0.0955 (8)
H3A1.38991.11910.74270.115*
C23A0.8727 (3)0.9022 (2)0.68673 (17)0.1026 (9)
H23A0.90180.94130.73420.123*
C25A0.7329 (3)0.8694 (2)0.57250 (17)0.0915 (8)
H25A0.67030.88550.54500.110*
C24A0.7822 (3)0.9249 (2)0.64444 (19)0.1076 (10)
H24A0.75210.97950.66410.129*
C2A1.4297 (3)0.9902 (2)0.69825 (17)0.1034 (9)
H2A1.49510.99600.73470.124*
Cl20.25579 (8)0.80531 (6)0.29088 (5)0.1130 (3)
N10.42346 (14)0.50306 (10)0.08849 (8)0.0506 (4)
H10.47580.46390.06580.061*
O20.37887 (13)0.61898 (9)0.01806 (7)0.0578 (3)
O30.07709 (15)0.79248 (11)0.07932 (8)0.0808 (5)
C50.41599 (17)0.46781 (13)0.16319 (9)0.0460 (4)
C90.35533 (17)0.59417 (12)0.04758 (10)0.0481 (4)
C80.25698 (18)0.65483 (13)0.08473 (10)0.0506 (4)
O10.15440 (15)0.66688 (11)0.19654 (8)0.0807 (5)
H1B0.11020.71840.16880.121*
C60.32825 (17)0.52679 (13)0.20136 (9)0.0493 (4)
C70.24411 (18)0.61846 (14)0.15949 (10)0.0538 (5)
C40.49435 (19)0.37465 (14)0.20066 (10)0.0562 (5)
H40.55020.33350.17500.067*
C100.1715 (2)0.75270 (13)0.04774 (11)0.0590 (5)
N20.24693 (19)0.96878 (12)0.03526 (10)0.0697 (5)
O40.42244 (19)0.83028 (12)0.12114 (9)0.0954 (5)
C110.19975 (19)0.81221 (13)0.02461 (10)0.0582 (5)
H110.22780.76700.05870.070*
C140.3108 (2)0.86168 (13)0.00994 (11)0.0610 (5)
C10.3245 (2)0.49299 (16)0.27839 (10)0.0614 (5)
H1C0.26650.53200.30450.074*
C170.5047 (2)0.77782 (14)0.07059 (13)0.0663 (6)
C120.0837 (2)0.90038 (14)0.06385 (11)0.0654 (5)
H120.02900.92300.02560.078*
C260.0001 (2)0.87571 (14)0.12084 (11)0.0619 (5)
C30.4885 (2)0.34408 (16)0.27551 (11)0.0635 (5)
H30.54150.28210.30060.076*
C160.5415 (2)0.76553 (14)0.00030 (13)0.0705 (6)
C150.4288 (2)0.81839 (15)0.05396 (13)0.0706 (6)
C20.4049 (2)0.40392 (17)0.31465 (11)0.0664 (5)
H20.40410.38290.36580.080*
C290.1581 (2)0.83325 (16)0.22557 (14)0.0750 (6)
C180.3755 (2)0.83578 (14)0.06875 (11)0.0621 (5)
C130.1477 (2)0.98141 (15)0.09448 (12)0.0738 (6)
H13C0.18530.97100.14050.089*
H13D0.08651.04750.10320.089*
C270.0457 (2)0.85014 (16)0.18572 (12)0.0702 (6)
H270.13160.84630.19420.084*
C280.0328 (2)0.83013 (17)0.23821 (14)0.0768 (6)
H280.00050.81460.28200.092*
C190.3316 (2)0.85706 (17)0.13402 (13)0.0747 (6)
H190.24810.89760.13470.090*
C220.5882 (2)0.73713 (17)0.13616 (15)0.0816 (7)
C300.2068 (2)0.85833 (18)0.16231 (16)0.0833 (7)
H300.29260.86130.15420.100*
C200.4139 (3)0.8171 (2)0.20033 (14)0.0934 (8)
H200.38280.83130.24470.112*
C310.1282 (2)0.87937 (17)0.11031 (14)0.0782 (7)
H310.16200.89640.06720.094*
C250.6667 (3)0.70967 (18)0.00608 (18)0.0930 (9)
H250.69430.70000.05220.112*
C240.7497 (3)0.6685 (2)0.0592 (2)0.1082 (10)
H240.83360.63090.05570.130*
C230.7139 (3)0.6808 (2)0.1272 (2)0.1065 (9)
H230.77330.65160.16870.128*
C210.5373 (3)0.7586 (2)0.20198 (16)0.0985 (8)
H210.58810.73270.24710.118*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C32A0.0926 (18)0.0802 (17)0.0974 (18)0.0097 (14)0.0261 (15)0.0334 (14)
C320.118 (2)0.0471 (13)0.110 (2)0.0209 (13)0.0116 (16)0.0110 (13)
Cl10.1231 (5)0.0841 (4)0.0700 (4)0.0476 (4)0.0330 (3)0.0220 (3)
O2A0.0723 (9)0.0502 (8)0.0663 (9)0.0224 (7)0.0062 (7)0.0126 (6)
N1A0.0671 (10)0.0449 (9)0.0631 (10)0.0162 (8)0.0005 (8)0.0136 (8)
C26A0.0662 (12)0.0434 (10)0.0591 (12)0.0203 (9)0.0036 (9)0.0066 (8)
C9A0.0557 (11)0.0468 (11)0.0559 (11)0.0126 (9)0.0083 (9)0.0178 (9)
C5A0.0642 (13)0.0516 (11)0.0614 (12)0.0058 (10)0.0009 (10)0.0173 (9)
C8A0.0556 (11)0.0514 (11)0.0631 (12)0.0188 (9)0.0062 (9)0.0137 (9)
O1A0.0820 (11)0.0842 (12)0.1344 (15)0.0466 (10)0.0283 (10)0.0082 (11)
C12A0.0648 (12)0.0447 (10)0.0625 (12)0.0194 (9)0.0018 (9)0.0110 (9)
C17A0.0762 (14)0.0562 (12)0.0611 (13)0.0121 (11)0.0249 (11)0.0190 (10)
C11A0.0623 (12)0.0446 (10)0.0544 (11)0.0200 (9)0.0053 (9)0.0137 (8)
N2A0.0746 (11)0.0531 (10)0.0670 (11)0.0132 (8)0.0123 (9)0.0195 (8)
O3A0.0756 (10)0.0684 (10)0.0934 (11)0.0391 (8)0.0030 (8)0.0004 (8)
C1OA0.0643 (12)0.0550 (12)0.0570 (11)0.0251 (10)0.0070 (9)0.0140 (9)
C18A0.0742 (13)0.0562 (12)0.0562 (12)0.0173 (10)0.0133 (10)0.0191 (9)
C29A0.0816 (15)0.0504 (11)0.0605 (12)0.0258 (10)0.0139 (11)0.0070 (9)
C30A0.0763 (14)0.0692 (14)0.0605 (13)0.0348 (11)0.0078 (10)0.0145 (10)
C16A0.0732 (14)0.0579 (12)0.0780 (15)0.0217 (11)0.0308 (12)0.0198 (11)
C6A0.0605 (13)0.0599 (13)0.0774 (14)0.0123 (10)0.0063 (11)0.0154 (11)
O4A0.0816 (11)0.0924 (12)0.0990 (12)0.0401 (9)0.0063 (10)0.0212 (10)
C7A0.0581 (12)0.0618 (13)0.0844 (15)0.0225 (10)0.0011 (11)0.0130 (11)
C14A0.0650 (12)0.0486 (11)0.0599 (12)0.0196 (9)0.0066 (9)0.0144 (9)
C31A0.0691 (13)0.0711 (14)0.0627 (13)0.0348 (11)0.0124 (10)0.0151 (10)
C28A0.0766 (15)0.0765 (15)0.0785 (15)0.0367 (12)0.0235 (12)0.0151 (12)
C13A0.0742 (14)0.0529 (12)0.0706 (14)0.0131 (10)0.0029 (11)0.0152 (10)
C21A0.109 (2)0.0867 (19)0.0549 (14)0.0004 (16)0.0100 (13)0.0230 (13)
C22A0.0988 (18)0.0615 (14)0.0623 (14)0.0055 (13)0.0302 (13)0.0133 (11)
C4A0.0942 (17)0.0582 (13)0.0764 (15)0.0141 (12)0.0101 (13)0.0100 (11)
C19A0.0951 (17)0.0732 (15)0.0628 (14)0.0263 (13)0.0058 (12)0.0263 (11)
C15A0.0617 (13)0.0621 (13)0.0771 (15)0.0200 (10)0.0135 (11)0.0223 (11)
C27A0.0682 (14)0.0758 (15)0.0742 (15)0.0342 (12)0.0066 (11)0.0143 (11)
C1A0.0781 (16)0.0748 (17)0.116 (2)0.0172 (13)0.0285 (15)0.0131 (15)
C20A0.1026 (19)0.0931 (19)0.0667 (16)0.0186 (16)0.0004 (13)0.0323 (14)
C3A0.115 (2)0.0696 (16)0.0849 (18)0.0073 (15)0.0279 (16)0.0075 (13)
C23A0.140 (3)0.0757 (18)0.0818 (19)0.0149 (18)0.0422 (18)0.0064 (15)
C25A0.0987 (19)0.0784 (17)0.111 (2)0.0388 (15)0.0459 (16)0.0272 (16)
C24A0.144 (3)0.0759 (19)0.108 (2)0.0412 (19)0.059 (2)0.0086 (17)
C2A0.103 (2)0.0806 (19)0.110 (2)0.0097 (16)0.0458 (17)0.0129 (16)
Cl20.0988 (5)0.0935 (5)0.1547 (7)0.0314 (4)0.0086 (5)0.0419 (5)
N10.0632 (9)0.0367 (8)0.0464 (8)0.0014 (7)0.0169 (7)0.0107 (6)
O20.0763 (9)0.0396 (7)0.0488 (7)0.0001 (6)0.0227 (6)0.0079 (5)
O30.0855 (10)0.0558 (9)0.0830 (10)0.0116 (8)0.0347 (8)0.0110 (7)
C50.0508 (10)0.0422 (9)0.0467 (10)0.0144 (8)0.0083 (8)0.0110 (8)
C90.0592 (11)0.0365 (9)0.0474 (10)0.0079 (8)0.0133 (8)0.0122 (8)
C80.0608 (11)0.0374 (9)0.0518 (10)0.0059 (8)0.0170 (9)0.0140 (8)
O10.0915 (11)0.0686 (9)0.0683 (9)0.0065 (8)0.0397 (8)0.0169 (7)
C60.0544 (11)0.0495 (10)0.0461 (10)0.0147 (9)0.0113 (8)0.0133 (8)
C70.0615 (11)0.0479 (10)0.0543 (11)0.0108 (9)0.0209 (9)0.0197 (9)
C40.0612 (12)0.0478 (11)0.0564 (12)0.0114 (9)0.0093 (9)0.0083 (9)
C100.0698 (13)0.0412 (10)0.0617 (12)0.0023 (9)0.0176 (10)0.0171 (9)
N20.0933 (13)0.0366 (9)0.0729 (11)0.0065 (9)0.0077 (10)0.0124 (8)
O40.1378 (15)0.0746 (11)0.0686 (11)0.0164 (10)0.0414 (10)0.0156 (8)
C110.0752 (13)0.0360 (9)0.0570 (11)0.0003 (9)0.0151 (10)0.0139 (8)
C140.0794 (14)0.0360 (10)0.0614 (12)0.0031 (9)0.0177 (10)0.0122 (8)
C10.0664 (13)0.0703 (14)0.0494 (11)0.0179 (11)0.0143 (9)0.0174 (10)
C170.0747 (14)0.0409 (10)0.0804 (15)0.0121 (10)0.0217 (12)0.0093 (10)
C120.0824 (14)0.0388 (10)0.0637 (12)0.0037 (10)0.0146 (11)0.0117 (9)
C260.0716 (14)0.0370 (10)0.0655 (13)0.0014 (9)0.0144 (10)0.0051 (9)
C30.0696 (13)0.0581 (12)0.0567 (12)0.0169 (10)0.0027 (10)0.0004 (10)
C160.0788 (15)0.0378 (10)0.0905 (16)0.0100 (10)0.0313 (13)0.0078 (10)
C150.1028 (17)0.0433 (11)0.0695 (14)0.0213 (11)0.0354 (13)0.0149 (10)
C20.0727 (14)0.0775 (15)0.0465 (11)0.0233 (12)0.0063 (10)0.0039 (10)
C290.0734 (15)0.0498 (12)0.0979 (18)0.0138 (11)0.0048 (13)0.0119 (12)
C180.0735 (14)0.0428 (10)0.0664 (13)0.0075 (10)0.0147 (10)0.0135 (9)
C130.1017 (17)0.0371 (10)0.0706 (14)0.0009 (11)0.0072 (13)0.0083 (10)
C270.0717 (14)0.0623 (13)0.0808 (15)0.0152 (11)0.0207 (12)0.0273 (11)
C280.0837 (16)0.0668 (14)0.0847 (16)0.0172 (12)0.0163 (13)0.0314 (12)
C190.0835 (15)0.0653 (14)0.0730 (15)0.0081 (12)0.0142 (12)0.0255 (11)
C220.0813 (17)0.0539 (13)0.0967 (19)0.0099 (12)0.0047 (14)0.0015 (13)
C300.0667 (15)0.0714 (16)0.0969 (19)0.0095 (12)0.0137 (14)0.0047 (14)
C200.111 (2)0.096 (2)0.0705 (17)0.0189 (17)0.0093 (15)0.0260 (14)
C310.0791 (16)0.0631 (14)0.0725 (15)0.0052 (12)0.0193 (13)0.0002 (11)
C250.0989 (19)0.0519 (13)0.127 (2)0.0150 (13)0.0582 (18)0.0150 (14)
C240.0811 (19)0.0586 (16)0.159 (3)0.0052 (13)0.029 (2)0.0060 (18)
C230.0848 (19)0.0738 (18)0.137 (3)0.0020 (15)0.0116 (18)0.0076 (17)
C210.106 (2)0.094 (2)0.0838 (19)0.0171 (17)0.0022 (16)0.0084 (15)
Geometric parameters (Å, º) top
C32A—N2A1.455 (3)C25A—C24A1.404 (4)
C32A—H32A0.9600C25A—H25A0.9300
C32A—H32B0.9600C24A—H24A0.9300
C32A—H32C0.9600C2A—H2A0.9300
C32—N21.451 (3)Cl2—C291.738 (3)
C32—H32D0.9600N1—C91.359 (2)
C32—H32E0.9600N1—C51.379 (2)
C32—H32F0.9600N1—H10.8600
Cl1—C29A1.737 (2)O2—C91.2431 (19)
O2A—C9A1.242 (2)O3—C101.244 (2)
N1A—C9A1.363 (2)C5—C61.392 (2)
N1A—C5A1.372 (2)C5—C41.393 (2)
N1A—H1A0.8600C9—C81.456 (2)
C26A—C31A1.381 (3)C8—C71.395 (2)
C26A—C27A1.385 (3)C8—C101.463 (3)
C26A—C12A1.506 (3)O1—C71.319 (2)
C9A—C8A1.454 (3)O1—H1B0.8200
C5A—C6A1.391 (3)C6—C11.409 (3)
C5A—C4A1.397 (3)C6—C71.426 (3)
C8A—C7A1.391 (3)C4—C31.368 (3)
C8A—C1OA1.464 (3)C4—H40.9300
O1A—C7A1.325 (2)C10—C111.515 (3)
O1A—H1'0.8200N2—C131.448 (3)
C12A—C13A1.516 (3)N2—C141.462 (2)
C12A—C11A1.553 (3)O4—C151.210 (3)
C12A—H12A0.9800C11—C121.547 (3)
C17A—C18A1.403 (3)C11—C141.576 (3)
C17A—C22A1.404 (3)C11—H110.9800
C17A—C16A1.400 (3)C14—C181.516 (3)
C11A—C1OA1.509 (3)C14—C151.578 (3)
C11A—C14A1.576 (3)C1—C21.355 (3)
C11A—H11A0.9800C1—H1C0.9300
N2A—C13A1.453 (3)C17—C161.394 (3)
N2A—C14A1.467 (2)C17—C221.403 (3)
O3A—C1OA1.243 (2)C17—C181.408 (3)
C18A—C19A1.366 (3)C12—C261.509 (3)
C18A—C14A1.513 (3)C12—C131.516 (3)
C29A—C30A1.366 (3)C12—H120.9800
C29A—C28A1.358 (3)C26—C271.382 (3)
C30A—C31A1.381 (3)C26—C311.385 (3)
C30A—H30A0.9300C3—C21.386 (3)
C16A—C25A1.378 (3)C3—H30.9300
C16A—C15A1.474 (3)C16—C251.390 (3)
C6A—C1A1.402 (3)C16—C151.472 (3)
C6A—C7A1.431 (3)C2—H20.9300
O4A—C15A1.205 (2)C29—C281.365 (3)
C14A—C15A1.567 (3)C29—C301.363 (3)
C31A—H31A0.9300C18—C191.363 (3)
C28A—C27A1.377 (3)C13—H13C0.9700
C28A—H28A0.9300C13—H13D0.9700
C13A—H13A0.9700C27—C281.379 (3)
C13A—H13B0.9700C27—H270.9300
C21A—C20A1.356 (4)C28—H280.9300
C21A—C22A1.407 (4)C19—C201.407 (3)
C21A—H21A0.9300C19—H190.9300
C22A—C23A1.412 (4)C22—C211.399 (4)
C4A—C3A1.372 (3)C22—C231.409 (4)
C4A—H4A0.9300C30—C311.381 (3)
C19A—C20A1.410 (3)C30—H300.9300
C19A—H19A0.9300C20—C211.360 (4)
C27A—H27A0.9300C20—H200.9300
C1A—C2A1.364 (4)C31—H310.9300
C1A—H1A20.9300C25—C241.397 (4)
C20A—H20A0.9300C25—H250.9300
C3A—C2A1.380 (4)C24—C231.350 (4)
C3A—H3A0.9300C24—H240.9300
C23A—C24A1.366 (4)C23—H230.9300
C23A—H23A0.9300C21—H210.9300
N2A—C32A—H32A109.5C23A—C24A—C25A122.8 (3)
N2A—C32A—H32B109.5C23A—C24A—H24A118.6
H32A—C32A—H32B109.5C25A—C24A—H24A118.6
N2A—C32A—H32C109.5C1A—C2A—C3A120.3 (2)
H32A—C32A—H32C109.5C1A—C2A—H2A119.8
H32B—C32A—H32C109.5C3A—C2A—H2A119.8
N2—C32—H32D109.5C9—N1—C5125.77 (14)
N2—C32—H32E109.5C9—N1—H1117.1
H32D—C32—H32E109.5C5—N1—H1117.1
N2—C32—H32F109.5N1—C5—C6119.05 (16)
H32D—C32—H32F109.5N1—C5—C4121.15 (15)
H32E—C32—H32F109.5C6—C5—C4119.81 (16)
C9A—N1A—C5A125.23 (16)O2—C9—N1118.77 (15)
C9A—N1A—H1A117.4O2—C9—C8124.93 (16)
C5A—N1A—H1A117.4N1—C9—C8116.28 (15)
C31A—C26A—C27A117.35 (19)C7—C8—C9118.54 (16)
C31A—C26A—C12A122.17 (17)C7—C8—C10118.20 (15)
C27A—C26A—C12A120.46 (18)C9—C8—C10123.25 (16)
O2A—C9A—N1A119.11 (16)C7—O1—H1B109.5
O2A—C9A—C8A124.22 (18)C5—C6—C1119.16 (17)
N1A—C9A—C8A116.67 (17)C5—C6—C7117.66 (16)
N1A—C5A—C6A119.46 (19)C1—C6—C7123.16 (16)
N1A—C5A—C4A120.48 (19)O1—C7—C8122.43 (17)
C6A—C5A—C4A120.1 (2)O1—C7—C6115.39 (16)
C7A—C8A—C9A118.57 (18)C8—C7—C6122.18 (15)
C7A—C8A—C1OA118.10 (17)C3—C4—C5119.52 (18)
C9A—C8A—C1OA122.87 (17)C3—C4—H4120.2
C7A—O1A—H1'109.5C5—C4—H4120.2
C26A—C12A—C13A117.09 (17)O3—C10—C8119.10 (17)
C26A—C12A—C11A113.32 (15)O3—C10—C11118.16 (16)
C13A—C12A—C11A103.07 (15)C8—C10—C11122.50 (16)
C26A—C12A—H12A107.6C13—N2—C32115.03 (18)
C13A—C12A—H12A107.6C13—N2—C14108.30 (16)
C11A—C12A—H12A107.6C32—N2—C14116.67 (19)
C18A—C17A—C22A123.3 (2)C10—C11—C12114.20 (16)
C18A—C17A—C16A113.06 (19)C10—C11—C14110.36 (16)
C22A—C17A—C16A123.6 (2)C12—C11—C14105.11 (15)
C1OA—C11A—C12A113.86 (15)C10—C11—H11109.0
C1OA—C11A—C14A111.75 (15)C12—C11—H11109.0
C12A—C11A—C14A105.22 (15)C14—C11—H11109.0
C1OA—C11A—H11A108.6N2—C14—C18112.58 (16)
C12A—C11A—H11A108.6N2—C14—C11102.88 (16)
C14A—C11A—H11A108.6C18—C14—C11117.16 (16)
C13A—N2A—C32A114.45 (18)N2—C14—C15115.27 (16)
C13A—N2A—C14A107.68 (15)C18—C14—C15101.09 (17)
C32A—N2A—C14A114.88 (17)C11—C14—C15108.35 (15)
O3A—C1OA—C8A119.25 (18)C2—C1—C6120.30 (18)
O3A—C1OA—C11A118.60 (18)C2—C1—H1C119.8
C8A—C1OA—C11A121.74 (16)C6—C1—H1C119.8
C19A—C18A—C17A118.7 (2)C16—C17—C22123.4 (2)
C19A—C18A—C14A131.97 (19)C16—C17—C18113.0 (2)
C17A—C18A—C14A109.37 (18)C22—C17—C18123.7 (2)
C30A—C29A—C28A120.9 (2)C26—C12—C13114.77 (17)
C30A—C29A—Cl1118.98 (17)C26—C12—C11114.95 (15)
C28A—C29A—Cl1120.12 (16)C13—C12—C11102.89 (18)
C29A—C30A—C31A119.4 (2)C26—C12—H12107.9
C29A—C30A—H30A120.3C13—C12—H12107.9
C31A—C30A—H30A120.3C11—C12—H12107.9
C25A—C16A—C17A119.9 (2)C27—C26—C31117.1 (2)
C25A—C16A—C15A132.5 (2)C27—C26—C12122.20 (19)
C17A—C16A—C15A107.48 (18)C31—C26—C12120.7 (2)
C5A—C6A—C1A119.2 (2)C4—C3—C2121.1 (2)
C5A—C6A—C7A117.73 (18)C4—C3—H3119.4
C1A—C6A—C7A123.0 (2)C2—C3—H3119.4
O1A—C7A—C8A121.9 (2)C25—C16—C17119.1 (2)
O1A—C7A—C6A116.07 (19)C25—C16—C15133.4 (2)
C8A—C7A—C6A121.84 (18)C17—C16—C15107.54 (18)
N2A—C14A—C18A111.66 (15)O4—C15—C16128.3 (2)
N2A—C14A—C15A114.73 (17)O4—C15—C14123.4 (2)
C18A—C14A—C15A102.04 (16)C16—C15—C14108.26 (18)
N2A—C14A—C11A102.73 (14)C1—C2—C3120.00 (19)
C18A—C14A—C11A117.97 (16)C1—C2—H2120.0
C15A—C14A—C11A108.19 (14)C3—C2—H2120.0
C30A—C31A—C26A121.32 (19)C28—C29—C30120.4 (2)
C30A—C31A—H31A119.3C28—C29—Cl2119.6 (2)
C26A—C31A—H31A119.3C30—C29—Cl2120.1 (2)
C29A—C28A—C27A119.4 (2)C19—C18—C17117.8 (2)
C29A—C28A—H28A120.3C19—C18—C14132.4 (2)
C27A—C28A—H28A120.3C17—C18—C14109.82 (17)
N2A—C13A—C12A102.47 (16)N2—C13—C12102.28 (17)
N2A—C13A—H13A111.3N2—C13—H13C111.3
C12A—C13A—H13A111.3C12—C13—H13C111.3
N2A—C13A—H13B111.3N2—C13—H13D111.3
C12A—C13A—H13B111.3C12—C13—H13D111.3
H13A—C13A—H13B109.2H13C—C13—H13D109.2
C20A—C21A—C22A120.5 (2)C26—C27—C28121.6 (2)
C20A—C21A—H21A119.8C26—C27—H27119.2
C22A—C21A—H21A119.8C28—C27—H27119.2
C17A—C22A—C23A114.9 (3)C29—C28—C27119.7 (2)
C17A—C22A—C21A116.2 (2)C29—C28—H28120.2
C23A—C22A—C21A128.9 (3)C27—C28—H28120.2
C3A—C4A—C5A119.3 (2)C18—C19—C20119.3 (2)
C3A—C4A—H4A120.3C18—C19—H19120.3
C5A—C4A—H4A120.3C20—C19—H19120.3
C18A—C19A—C20A118.7 (2)C21—C22—C17116.3 (2)
C18A—C19A—H19A120.7C21—C22—C23128.1 (3)
C20A—C19A—H19A120.7C17—C22—C23115.6 (3)
O4A—C15A—C16A127.9 (2)C29—C30—C31119.7 (2)
O4A—C15A—C14A124.3 (2)C29—C30—H30120.2
C16A—C15A—C14A107.87 (18)C31—C30—H30120.2
C28A—C27A—C26A121.6 (2)C21—C20—C19122.5 (2)
C28A—C27A—H27A119.2C21—C20—H20118.8
C26A—C27A—H27A119.2C19—C20—H20118.8
C2A—C1A—C6A120.2 (2)C30—C31—C26121.5 (2)
C2A—C1A—H1A2119.9C30—C31—H31119.3
C6A—C1A—H1A2119.9C26—C31—H31119.3
C21A—C20A—C19A122.6 (2)C24—C25—C16117.6 (3)
C21A—C20A—H20A118.7C24—C25—H25121.2
C19A—C20A—H20A118.7C16—C25—H25121.2
C4A—C3A—C2A120.9 (2)C23—C24—C25123.2 (3)
C4A—C3A—H3A119.5C23—C24—H24118.4
C2A—C3A—H3A119.5C25—C24—H24118.4
C24A—C23A—C22A121.5 (3)C24—C23—C22121.1 (3)
C24A—C23A—H23A119.2C24—C23—H23119.5
C22A—C23A—H23A119.2C22—C23—H23119.5
C16A—C25A—C24A117.3 (3)C20—C21—C22120.4 (3)
C16A—C25A—H25A121.4C20—C21—H21119.8
C24A—C25A—H25A121.4C22—C21—H21119.8
C5A—N1A—C9A—O2A178.65 (17)C9—N1—C5—C62.8 (3)
C5A—N1A—C9A—C8A1.5 (3)C9—N1—C5—C4177.24 (17)
C9A—N1A—C5A—C6A5.3 (3)C5—N1—C9—O2174.73 (16)
C9A—N1A—C5A—C4A173.83 (19)C5—N1—C9—C86.5 (3)
O2A—C9A—C8A—C7A174.88 (18)O2—C9—C8—C7178.09 (17)
N1A—C9A—C8A—C7A5.0 (3)N1—C9—C8—C73.3 (3)
O2A—C9A—C8A—C1OA13.1 (3)O2—C9—C8—C101.3 (3)
N1A—C9A—C8A—C1OA167.00 (17)N1—C9—C8—C10177.30 (17)
C31A—C26A—C12A—C13A39.2 (3)N1—C5—C6—C1177.17 (16)
C27A—C26A—C12A—C13A142.7 (2)C4—C5—C6—C12.9 (3)
C31A—C26A—C12A—C11A80.6 (2)N1—C5—C6—C74.1 (2)
C27A—C26A—C12A—C11A97.5 (2)C4—C5—C6—C7175.84 (16)
C26A—C12A—C11A—C1OA91.64 (19)C9—C8—C7—O1177.44 (17)
C13A—C12A—C11A—C1OA140.83 (16)C10—C8—C7—O13.1 (3)
C26A—C12A—C11A—C14A145.66 (16)C9—C8—C7—C63.3 (3)
C13A—C12A—C11A—C14A18.14 (18)C10—C8—C7—C6176.12 (17)
C7A—C8A—C1OA—O3A18.4 (3)C5—C6—C7—O1173.65 (16)
C9A—C8A—C1OA—O3A169.59 (18)C1—C6—C7—O15.0 (3)
C7A—C8A—C1OA—C11A154.14 (18)C5—C6—C7—C87.1 (3)
C9A—C8A—C1OA—C11A17.9 (3)C1—C6—C7—C8174.24 (18)
C12A—C11A—C1OA—O3A14.0 (2)N1—C5—C4—C3177.04 (17)
C14A—C11A—C1OA—O3A105.0 (2)C6—C5—C4—C33.0 (3)
C12A—C11A—C1OA—C8A173.43 (16)C7—C8—C10—O311.8 (3)
C14A—C11A—C1OA—C8A67.5 (2)C9—C8—C10—O3168.74 (18)
C22A—C17A—C18A—C19A3.7 (3)C7—C8—C10—C11162.55 (18)
C16A—C17A—C18A—C19A176.78 (18)C9—C8—C10—C1116.9 (3)
C22A—C17A—C18A—C14A175.55 (18)O3—C10—C11—C1219.2 (3)
C16A—C17A—C18A—C14A4.0 (2)C8—C10—C11—C12166.32 (17)
C28A—C29A—C30A—C31A1.4 (3)O3—C10—C11—C1498.9 (2)
Cl1—C29A—C30A—C31A177.19 (17)C8—C10—C11—C1475.5 (2)
C18A—C17A—C16A—C25A179.23 (19)C13—N2—C14—C18157.09 (18)
C22A—C17A—C16A—C25A0.3 (3)C32—N2—C14—C1871.2 (2)
C18A—C17A—C16A—C15A1.8 (2)C13—N2—C14—C1130.1 (2)
C22A—C17A—C16A—C15A177.77 (19)C32—N2—C14—C11161.73 (18)
N1A—C5A—C6A—C1A178.5 (2)C13—N2—C14—C1587.7 (2)
C4A—C5A—C6A—C1A0.6 (3)C32—N2—C14—C1544.0 (3)
N1A—C5A—C6A—C7A2.5 (3)C10—C11—C14—N2119.19 (16)
C4A—C5A—C6A—C7A176.7 (2)C12—C11—C14—N24.39 (18)
C9A—C8A—C7A—O1A176.95 (19)C10—C11—C14—C184.9 (2)
C1OA—C8A—C7A—O1A10.7 (3)C12—C11—C14—C18128.44 (16)
C9A—C8A—C7A—C6A7.8 (3)C10—C11—C14—C15118.31 (17)
C1OA—C8A—C7A—C6A164.64 (19)C12—C11—C14—C15118.11 (17)
C5A—C6A—C7A—O1A179.6 (2)C5—C6—C1—C20.3 (3)
C1A—C6A—C7A—O1A3.6 (3)C7—C6—C1—C2178.35 (19)
C5A—C6A—C7A—C8A4.0 (3)C10—C11—C12—C2692.7 (2)
C1A—C6A—C7A—C8A171.9 (2)C14—C11—C12—C26146.23 (17)
C13A—N2A—C14A—C18A159.82 (16)C10—C11—C12—C13141.83 (17)
C32A—N2A—C14A—C18A71.4 (2)C14—C11—C12—C1320.75 (19)
C13A—N2A—C14A—C15A84.7 (2)C13—C12—C26—C2753.7 (2)
C32A—N2A—C14A—C15A44.1 (2)C11—C12—C26—C2765.4 (2)
C13A—N2A—C14A—C11A32.44 (19)C13—C12—C26—C31125.4 (2)
C32A—N2A—C14A—C11A161.25 (17)C11—C12—C26—C31115.6 (2)
C19A—C18A—C14A—N2A53.7 (3)C5—C4—C3—C20.6 (3)
C17A—C18A—C14A—N2A127.23 (17)C22—C17—C16—C250.5 (3)
C19A—C18A—C14A—C15A176.7 (2)C18—C17—C16—C25179.89 (19)
C17A—C18A—C14A—C15A4.2 (2)C22—C17—C16—C15179.9 (2)
C19A—C18A—C14A—C11A65.0 (3)C18—C17—C16—C150.5 (2)
C17A—C18A—C14A—C11A114.12 (18)C25—C16—C15—O45.0 (4)
C1OA—C11A—C14A—N2A116.54 (16)C17—C16—C15—O4175.7 (2)
C12A—C11A—C14A—N2A7.50 (18)C25—C16—C15—C14176.1 (2)
C1OA—C11A—C14A—C18A6.7 (2)C17—C16—C15—C143.2 (2)
C12A—C11A—C14A—C18A130.75 (17)N2—C14—C15—O452.1 (3)
C1OA—C11A—C14A—C15A121.74 (17)C18—C14—C15—O4173.7 (2)
C12A—C11A—C14A—C15A114.22 (17)C11—C14—C15—O462.6 (2)
C29A—C30A—C31A—C26A0.8 (3)N2—C14—C15—C16126.98 (19)
C27A—C26A—C31A—C30A0.7 (3)C18—C14—C15—C165.3 (2)
C12A—C26A—C31A—C30A177.51 (19)C11—C14—C15—C16118.42 (18)
C30A—C29A—C28A—C27A0.5 (3)C6—C1—C2—C32.1 (3)
Cl1—C29A—C28A—C27A178.10 (18)C4—C3—C2—C12.0 (3)
C32A—N2A—C13A—C12A174.14 (17)C16—C17—C18—C19176.49 (19)
C14A—N2A—C13A—C12A45.08 (19)C22—C17—C18—C193.1 (3)
C26A—C12A—C13A—N2A162.62 (15)C16—C17—C18—C144.2 (2)
C11A—C12A—C13A—N2A37.51 (18)C22—C17—C18—C14176.22 (19)
C18A—C17A—C22A—C23A178.5 (2)N2—C14—C18—C1951.6 (3)
C16A—C17A—C22A—C23A1.0 (3)C11—C14—C18—C1967.3 (3)
C18A—C17A—C22A—C21A1.5 (3)C15—C14—C18—C19175.2 (2)
C16A—C17A—C22A—C21A179.03 (19)N2—C14—C18—C17129.17 (18)
C20A—C21A—C22A—C17A1.4 (3)C11—C14—C18—C17111.84 (19)
C20A—C21A—C22A—C23A178.6 (2)C15—C14—C18—C175.6 (2)
N1A—C5A—C4A—C3A177.7 (2)C32—N2—C13—C12176.79 (17)
C6A—C5A—C4A—C3A1.4 (3)C14—N2—C13—C1244.2 (2)
C17A—C18A—C19A—C20A2.9 (3)C26—C12—C13—N2164.24 (16)
C14A—C18A—C19A—C20A176.1 (2)C11—C12—C13—N238.63 (18)
C25A—C16A—C15A—O4A3.7 (4)C31—C26—C27—C280.7 (3)
C17A—C16A—C15A—O4A179.3 (2)C12—C26—C27—C28178.40 (19)
C25A—C16A—C15A—C14A175.9 (2)C30—C29—C28—C271.6 (3)
C17A—C16A—C15A—C14A1.1 (2)Cl2—C29—C28—C27178.59 (17)
N2A—C14A—C15A—O4A56.3 (3)C26—C27—C28—C291.5 (3)
C18A—C14A—C15A—O4A177.2 (2)C17—C18—C19—C202.8 (3)
C11A—C14A—C15A—O4A57.7 (3)C14—C18—C19—C20176.3 (2)
N2A—C14A—C15A—C16A124.08 (18)C16—C17—C22—C21178.3 (2)
C18A—C14A—C15A—C16A3.2 (2)C18—C17—C22—C211.2 (3)
C11A—C14A—C15A—C16A121.92 (17)C16—C17—C22—C230.7 (3)
C29A—C28A—C27A—C26A1.1 (3)C18—C17—C22—C23179.7 (2)
C31A—C26A—C27A—C28A1.6 (3)C28—C29—C30—C310.9 (3)
C12A—C26A—C27A—C28A176.6 (2)Cl2—C29—C30—C31179.30 (17)
C5A—C6A—C1A—C2A0.8 (4)C18—C19—C20—C210.9 (4)
C7A—C6A—C1A—C2A175.1 (3)C29—C30—C31—C260.1 (3)
C22A—C21A—C20A—C19A2.1 (4)C27—C26—C31—C300.0 (3)
C18A—C19A—C20A—C21A0.1 (4)C12—C26—C31—C30179.13 (19)
C5A—C4A—C3A—C2A0.9 (4)C17—C16—C25—C240.1 (3)
C17A—C22A—C23A—C24A0.6 (4)C15—C16—C25—C24179.3 (2)
C21A—C22A—C23A—C24A179.4 (3)C16—C25—C24—C230.2 (4)
C17A—C16A—C25A—C24A0.7 (3)C25—C24—C23—C220.1 (5)
C15A—C16A—C25A—C24A176.0 (2)C21—C22—C23—C24178.4 (3)
C22A—C23A—C24A—C25A0.4 (4)C17—C22—C23—C240.5 (4)
C16A—C25A—C24A—C23A1.1 (4)C19—C20—C21—C221.1 (5)
C6A—C1A—C2A—C3A1.4 (5)C17—C22—C21—C200.9 (4)
C4A—C3A—C2A—C1A0.5 (5)C23—C22—C21—C20178.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.879 (2)171
O1—H1B···O30.821.742.468 (2)147
N1A—H1A···O2Aii0.862.012.865 (2)174
O1A—H1···O3A0.821.752.477 (2)148
C3A—H3A···O4iii0.932.453.245 (3)143
C13—H13D···O3iv0.972.603.530 (3)161
C30A—H30A···O2v0.932.543.413 (2)157
Symmetry codes: (i) x1, y+1, z; (ii) x+2, y+2, z+1; (iii) x+1, y+2, z+1; (iv) x, y+2, z; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC32H23ClN2O4
Mr534.97
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.7447 (7), 14.1678 (9), 18.3858 (11)
α, β, γ (°)101.328 (3), 91.945 (3), 105.388 (3)
V3)2635.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.25 × 0.24 × 0.21
Data collection
DiffractometerBruker SMART APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.954, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
47617, 13107, 6910
Rint0.029
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.151, 0.94
No. of reflections13107
No. of parameters705
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.42

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.879 (2)171
O1—H1B···O30.821.742.468 (2)147
N1A—H1A···O2Aii0.862.012.865 (2)174
O1A—H1'···O3A0.821.752.477 (2)148
C3A—H3A···O4iii0.932.453.245 (3)143
C30A—H30A···O2iv0.932.543.413 (2)157
Symmetry codes: (i) x1, y+1, z; (ii) x+2, y+2, z+1; (iii) x+1, y+2, z+1; (iv) x+1, y, z.
 

Acknowledgements

KNV thanks the CSIR, New Delhi, for financial assistance in the form of a Senior Research Fellowship. The authors acknowledge the Department of Science and Technology (DST) for providing data-collection facilities under the TBI Program and also thank the UGC-SAP and DST-FIST for financial support to the Department.

References

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