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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Pages o2772-o2773

1-Methyl-1′-(4-methyl­phen­yl)-2′,3′,5′,6′,7′,7a'-hexa­hydro-1′H-di­spiro­[piperidine-3,2′-pyrrolizine-3′,3′′-indoline]-4,2′′-dione

aDepartment of Physics, N.M.S.S. Vellaichamy Nadar College, Madurai 625 019, India, bDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and cSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
*Correspondence e-mail: vasan692000@yahoo.co.in

(Received 5 July 2012; accepted 19 August 2012; online 25 August 2012)

The title compound, C26H29N3O2, crystallizes with two mol­ecules in the asymmetric unit, having C—H⋯O inter­actions between them and resulting in a dimer characterized by an R22(11) motif. These dimers are linked into an ABABAB chain via N—H⋯O, N—H⋯N and C—H⋯O built edge-fused R12(5) and R22(7) motifs. This chain is linked to its inversion-related partner via N—H⋯O bonds with an R22(8) motif and leads to a double chain extending along the b axis characterized by an R66(36) motif across the inversion centres. The methyl group of the phenyl ring and the oxindole of mol­ecule A and B are involved in C—H⋯π inter­actions. One C atom of the pyrrolizine ring of mol­ecule A and its attached H atoms show positional disorder, the major and minor components being in the ratio 0.706 (7):0.294 (7).

Related literature

For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H29N3O2

  • Mr = 415.52

  • Triclinic, [P \overline 1]

  • a = 8.7516 (4) Å

  • b = 12.4649 (5) Å

  • c = 21.4605 (8) Å

  • α = 97.654 (2)°

  • β = 101.024 (2)°

  • γ = 102.345 (2)°

  • V = 2207.45 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.28 × 0.19 × 0.19 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.93, Tmax = 0.96

  • 44464 measured reflections

  • 7765 independent reflections

  • 5493 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.110

  • S = 1.02

  • 7765 reflections

  • 574 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20A–C25A and C20B–C25B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2A⋯O1Ai 0.86 1.99 2.8331 (17) 167
N2B—H2B⋯O1Aii 0.86 2.48 3.0829 (18) 128
N2B—H2B⋯N1Aii 0.86 2.24 3.0461 (18) 156
C4A—H4A⋯O1Biii 0.98 2.52 3.4598 (19) 160
C16B—H16C⋯O2A 0.97 2.47 3.431 (2) 171
C5A—H52A⋯O2B 0.97 2.58 3.404 (2) 143
C6A—H63ACg1iv 0.97 2.97 3.819 (9) 147
C6B—H62BCg2iv 0.97 2.93 3.827 (3) 155
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x, y-1, z; (iii) x, y+1, z; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: PLUTON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound contains two molecules in the asymmetric unit forming an asymmetric dimer through C—H···O hydrogen bonds between them. The molecular structure with displacement ellipsoids drawn at 50% probability level is shown in Fig.1. The C8—O1 distance in the indolone in molecules A and B are 1.2244 (18)and 1.215 (2) A°, respectively. The difference in the C8—O1 bond distances in molecules A and B is substantiated by the deviation of O1 from the plane by about 0.4122 (18) in molecule A and 0.2907 (21) in molecule B. This deviation of O1 from planarity seems to have considerably influenced differences in the values of the torsion angles N1—C1–C8—O1 and C2—C1—C8—O1 of molecules A and B. In molecule A, these torsion angles are 37.5 (2) and -75.6 (2)° while in B these values are -53.8 (2) and 61.0 (2)°, respectively. These differences in conformation may also be attributed to a significant intermolecular feature that O1A participates in a three-centered hydrogen bond involving N—H···O and N—H···N types and O1B in a C—H···O type hydrogen bond.

The carbon atom C6 in the hexahydropyrrolizine ring of molecule A shows positional disorder with major and minor component of 0.71 and 0.29, respectively for its site occupancy factor. This disorder leads to a flipping of the conformation of the N1—C4—C5—C6—C7 ring with the puckering parameters (Cremer & Pople, 1975) observed as twisted on C5—C6 with q=0.393 Å, ϕ=271.4 (3)° for the major component and twisted on C6—C7 with q=0.347 (5) Å, ϕ=125.0 (7) ° for the minor component. The corresponding ring in molecule B shows similar twist conformation but with the twist on N1—C4 with q=0.394 (2) Å, ϕ=15.9 (4) °. The puckering of the five-membered ring N1—C1—C2—C3—C4 of the pyrrolizine is envelope (3E) on atom C2 with q = 0.3615 (17) Å, ϕ = 66.3 (3)° in molecule A and envelope (E5) on atom C4 with q = 0.4364 (19) Å, ϕ = 320.7 (2) ° in molecule B. The puckering of the piperidinone rings in both the molecules is close to the usual chair with Q = 0.551 (2) Å, θ = 24.0 (2)°, ϕ = 353.7 (8)° for molecule A and Q = 0.559 (2) Å, θ = 16.4 (2)°, ϕ = 339.4 (8)° for molecule B. The hydrogen-bonded interaction (Table 1) between molecules generate one-dimensional double chains extending along the b axis (Fig.2).

The molecular interaction pattern is characterized by four different graph-set motifs (Bernstein et al., 1995) viz. R22(8), R22(7), R21(5) and a R22(11) type. The R22(11) motif occurs between the two molecules in the asymmetric unit through C—H···O hydrogen bonds. The R22(8) is built across inversion centres through N—H···O hydrogen bonds. R22(7) is edge fused with a R21(6) motif, in which the N—H···N bond is the shared edge, while C—H···O and N—H···O, respectively are their respective characteristic units. An interesting feature is that all these fundamental simple graph-set motifs lead to a complex R66(36) motif across the inversion centres. Also two significant C—H···π viz. C6A—H63A···Cg1(C20AC25A) and C6B—H62B···Cg2 (C20BC25B) interactions are observed. Thus, the presence of a variety of interaction patterns in the crystal structure of a geometrically unfathomable molecule may well be regarded significant in the context of crystal structure prediction.

Related literature top

For ring puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Refinement top

H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

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

Figures top
Fig. 1. Overlay diagram of the two molecules A (Red) and B (Black) in the asymmetric unit

Fig. 2. The labelling scheme of molecule A with 50% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.

Fig. 3. A view of the molecular aggregation along the b--axis. H atoms that are not involved in hydrogen bonding have been omitted for clarity.
1-Methyl-1'-(4-methylphenyl)-2',3',5',6',7',7a'-hexahydro-1'H- dispiro[piperidine-3,2'-pyrrolizine-3',3''-indoline]-4,2''-dione top
Crystal data top
C26H29N3O2Z = 4
Mr = 415.52F(000) = 888
Triclinic, P1Dx = 1.250 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7516 (4) ÅCell parameters from 5520 reflections
b = 12.4649 (5) Åθ = 2.4–23.9°
c = 21.4605 (8) ŵ = 0.08 mm1
α = 97.654 (2)°T = 293 K
β = 101.024 (2)°Block, colourless
γ = 102.345 (2)°0.28 × 0.19 × 0.19 mm
V = 2207.45 (16) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7765 independent reflections
Radiation source: fine-focus sealed tube5493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω and ϕ scanθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1010
Tmin = 0.93, Tmax = 0.96k = 1414
44464 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.5445P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
7765 reflectionsΔρmax = 0.21 e Å3
574 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0037 (7)
Crystal data top
C26H29N3O2γ = 102.345 (2)°
Mr = 415.52V = 2207.45 (16) Å3
Triclinic, P1Z = 4
a = 8.7516 (4) ÅMo Kα radiation
b = 12.4649 (5) ŵ = 0.08 mm1
c = 21.4605 (8) ÅT = 293 K
α = 97.654 (2)°0.28 × 0.19 × 0.19 mm
β = 101.024 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7765 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5493 reflections with I > 2σ(I)
Tmin = 0.93, Tmax = 0.96Rint = 0.037
44464 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
7765 reflectionsΔρmin = 0.17 e Å3
574 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 F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.94742 (14)0.97304 (9)0.41175 (5)0.0410 (3)
O2A0.66024 (15)0.52962 (10)0.36307 (6)0.0506 (3)
N1A0.98111 (15)0.80851 (10)0.31517 (6)0.0330 (3)
N2A1.02786 (17)0.86038 (11)0.48069 (6)0.0432 (4)
H2A1.04320.90460.51690.052*
N3A0.63813 (17)0.84523 (12)0.41103 (7)0.0446 (4)
C1A0.92833 (18)0.77439 (12)0.37159 (7)0.0309 (4)
C2A0.74340 (18)0.71642 (12)0.34351 (7)0.0308 (4)
C3A0.74369 (18)0.66023 (12)0.27416 (7)0.0315 (4)
H3A0.77650.59060.27810.038*
C4A0.87877 (19)0.73809 (13)0.25463 (7)0.0334 (4)
H4A0.83260.78580.22750.040*
C5A0.9919 (2)0.68726 (16)0.22146 (9)0.0507 (5)
H51A0.95430.67240.17490.061*
H52A1.00570.61870.23590.061*
C6AA1.1467 (3)0.7797 (3)0.24341 (15)0.0532 (11)0.706 (7)
H61A1.23950.75070.23940.064*0.706 (7)
H62A1.14370.83900.21860.064*0.706 (7)
C6A1.1412 (9)0.7035 (9)0.2653 (4)0.067 (3)0.294 (7)
H63A1.22910.71160.24340.080*0.294 (7)
H64A1.14240.64250.28890.080*0.294 (7)
C7A1.1497 (2)0.81995 (17)0.31269 (9)0.0504 (5)
H71A1.19830.77490.34030.061*
H72A1.21000.89720.32650.061*
C8A0.96279 (19)0.88168 (13)0.42297 (8)0.0345 (4)
C9A1.0674 (2)0.75700 (14)0.47431 (8)0.0397 (4)
C10A1.1479 (2)0.71193 (16)0.52181 (9)0.0541 (5)
H10A1.17980.74910.56450.065*
C11A1.1795 (3)0.60970 (18)0.50390 (11)0.0608 (6)
H11A1.23460.57770.53490.073*
C12A1.1307 (2)0.55462 (16)0.44085 (10)0.0555 (5)
H12A1.15360.48600.42980.067*
C13A1.0476 (2)0.60007 (14)0.39347 (9)0.0441 (4)
H13A1.01350.56200.35100.053*
C14A1.01634 (19)0.70280 (13)0.41043 (8)0.0349 (4)
C15A0.67971 (19)0.62814 (14)0.38218 (8)0.0374 (4)
C16A0.6375 (3)0.66840 (17)0.44407 (9)0.0542 (5)
H16A0.73520.69650.47760.065*
H16B0.57110.60610.45690.065*
C17A0.5490 (2)0.75934 (18)0.43833 (10)0.0583 (5)
H17A0.44250.72870.41090.070*
H17B0.53790.79080.48060.070*
C18A0.6423 (2)0.80318 (14)0.34508 (8)0.0378 (4)
H18A0.68790.86470.32560.045*
H18B0.53380.76920.32020.045*
C19A0.5855 (3)0.94882 (17)0.41722 (10)0.0622 (6)
H19A0.47590.93480.39400.093*
H19B0.65221.00320.39980.093*
H19C0.59380.97660.46200.093*
C20A0.58431 (19)0.62975 (13)0.22520 (7)0.0334 (4)
C21A0.4860 (2)0.52211 (15)0.21288 (9)0.0485 (5)
H21A0.51710.46920.23590.058*
C22A0.3429 (2)0.49259 (17)0.16709 (9)0.0571 (5)
H22A0.27950.42010.16010.068*
C23A0.2911 (2)0.56729 (17)0.13138 (9)0.0504 (5)
C24A0.3886 (2)0.67381 (16)0.14344 (9)0.0476 (5)
H24A0.35720.72630.12010.057*
C25A0.5316 (2)0.70464 (14)0.18928 (8)0.0417 (4)
H25A0.59410.77740.19620.050*
C26A0.1373 (3)0.5351 (2)0.08001 (11)0.0786 (7)
H26A0.14550.47990.04590.118*
H26B0.11910.59990.06300.118*
H26C0.04940.50490.09840.118*
O1B0.80365 (16)0.04225 (10)0.18075 (6)0.0539 (3)
O2B0.8647 (2)0.41105 (11)0.22578 (7)0.0696 (4)
N1B1.01620 (19)0.16146 (13)0.15026 (7)0.0503 (4)
N2B0.97215 (18)0.03574 (12)0.27920 (7)0.0473 (4)
H2B0.95830.02170.29760.057*
N3B0.61912 (19)0.10803 (13)0.24203 (8)0.0528 (4)
C1B0.9443 (2)0.15839 (13)0.20515 (8)0.0398 (4)
C2B0.7965 (2)0.21432 (13)0.18396 (8)0.0393 (4)
C3B0.8158 (2)0.24387 (14)0.11669 (8)0.0439 (4)
H3B0.89380.31640.12540.053*
C4B0.8991 (2)0.15759 (15)0.09240 (8)0.0472 (5)
H4B0.82420.08370.07900.057*
C5B1.0059 (3)0.1781 (2)0.04515 (11)0.0700 (6)
H51B1.04560.25740.04650.084*
H52B0.94850.14290.00140.084*
C6B1.1438 (3)0.1248 (2)0.06857 (12)0.0817 (7)
H61B1.13640.05720.03870.098*
H62B1.24670.17620.07210.098*
C7B1.1265 (3)0.0981 (2)0.13420 (11)0.0717 (6)
H71B1.08290.01880.13170.086*
H72B1.22860.12200.16540.086*
C8B0.8908 (2)0.03814 (14)0.21913 (9)0.0417 (4)
C9B1.0814 (2)0.13785 (15)0.30764 (9)0.0437 (4)
C10B1.1940 (2)0.16449 (18)0.36528 (9)0.0579 (5)
H10B1.20000.11380.39320.069*
C11B1.2979 (3)0.26945 (19)0.37998 (10)0.0642 (6)
H11B1.37560.28930.41850.077*
C12B1.2894 (3)0.34531 (18)0.33923 (10)0.0626 (6)
H12B1.36120.41520.35030.075*
C13B1.1745 (2)0.31804 (15)0.28186 (10)0.0546 (5)
H13B1.16840.36920.25420.065*
C14B1.0691 (2)0.21393 (14)0.26617 (8)0.0421 (4)
C15B0.8128 (2)0.31757 (15)0.23421 (9)0.0486 (5)
C16B0.7613 (3)0.29696 (18)0.29528 (10)0.0628 (6)
H16C0.74530.36560.31710.075*
H16D0.84660.27650.32360.075*
C17B0.6081 (3)0.20570 (19)0.28375 (10)0.0658 (6)
H17C0.59090.18650.32460.079*
H17D0.51740.23230.26400.079*
C18B0.6336 (2)0.13550 (15)0.17934 (9)0.0457 (4)
H18C0.54880.17060.16340.055*
H18D0.62130.06750.14900.055*
C19B0.4850 (3)0.0124 (2)0.23642 (13)0.0766 (7)
H19D0.48180.00530.27840.115*
H19E0.49840.05060.20890.115*
H19F0.38640.03020.21820.115*
C20B0.6676 (2)0.25512 (15)0.07119 (9)0.0481 (5)
C21B0.6182 (3)0.35393 (18)0.07883 (10)0.0635 (6)
H21B0.67410.41140.11310.076*
C22B0.4870 (3)0.3677 (2)0.03610 (11)0.0699 (6)
H22B0.45590.43440.04240.084*
C23B0.4009 (3)0.2852 (2)0.01565 (10)0.0628 (6)
C24B0.4502 (3)0.1881 (2)0.02321 (10)0.0642 (6)
H24B0.39470.13110.05780.077*
C25B0.5807 (3)0.17275 (17)0.01928 (9)0.0569 (5)
H25B0.61070.10560.01280.068*
C26B0.2593 (3)0.3020 (3)0.06182 (11)0.0868 (8)
H26D0.18860.32890.03800.130*
H26E0.20290.23230.08970.130*
H26F0.29610.35560.08730.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0532 (8)0.0308 (6)0.0359 (7)0.0096 (5)0.0057 (6)0.0029 (5)
O2A0.0578 (8)0.0402 (7)0.0510 (8)0.0025 (6)0.0136 (6)0.0127 (6)
N1A0.0292 (7)0.0360 (7)0.0295 (7)0.0022 (6)0.0042 (6)0.0038 (6)
N2A0.0561 (10)0.0402 (8)0.0268 (8)0.0130 (7)0.0021 (7)0.0016 (6)
N3A0.0440 (9)0.0538 (9)0.0367 (8)0.0180 (7)0.0110 (7)0.0018 (7)
C1A0.0315 (9)0.0302 (8)0.0280 (8)0.0063 (7)0.0028 (7)0.0027 (6)
C2A0.0308 (9)0.0327 (8)0.0263 (8)0.0063 (7)0.0042 (7)0.0026 (6)
C3A0.0339 (9)0.0295 (8)0.0290 (8)0.0063 (7)0.0049 (7)0.0036 (6)
C4A0.0334 (9)0.0357 (9)0.0284 (9)0.0061 (7)0.0036 (7)0.0051 (7)
C5A0.0517 (12)0.0541 (11)0.0456 (11)0.0101 (9)0.0190 (10)0.0009 (9)
C6AA0.0420 (17)0.064 (2)0.057 (2)0.0122 (14)0.0213 (14)0.0091 (16)
C6A0.057 (5)0.109 (8)0.055 (5)0.044 (5)0.027 (4)0.026 (5)
C7A0.0315 (10)0.0657 (12)0.0488 (12)0.0039 (9)0.0061 (9)0.0093 (9)
C8A0.0348 (9)0.0330 (9)0.0321 (9)0.0057 (7)0.0035 (7)0.0039 (7)
C9A0.0404 (10)0.0392 (9)0.0367 (10)0.0087 (8)0.0022 (8)0.0090 (8)
C10A0.0615 (13)0.0588 (12)0.0382 (11)0.0153 (10)0.0020 (9)0.0143 (9)
C11A0.0616 (14)0.0635 (13)0.0639 (14)0.0240 (11)0.0055 (11)0.0327 (11)
C12A0.0588 (13)0.0443 (11)0.0685 (14)0.0218 (9)0.0111 (11)0.0186 (10)
C13A0.0450 (11)0.0382 (9)0.0490 (11)0.0141 (8)0.0063 (9)0.0072 (8)
C14A0.0321 (9)0.0342 (9)0.0366 (10)0.0064 (7)0.0042 (7)0.0087 (7)
C15A0.0313 (9)0.0432 (10)0.0339 (9)0.0041 (8)0.0030 (7)0.0084 (8)
C16A0.0607 (13)0.0633 (12)0.0406 (11)0.0083 (10)0.0200 (10)0.0153 (9)
C17A0.0533 (13)0.0798 (14)0.0455 (12)0.0173 (11)0.0223 (10)0.0062 (10)
C18A0.0345 (10)0.0432 (9)0.0338 (9)0.0121 (8)0.0034 (7)0.0023 (7)
C19A0.0554 (13)0.0682 (13)0.0611 (13)0.0292 (11)0.0084 (10)0.0110 (10)
C20A0.0337 (9)0.0374 (9)0.0253 (8)0.0050 (7)0.0063 (7)0.0006 (7)
C21A0.0512 (12)0.0430 (10)0.0397 (10)0.0021 (9)0.0008 (9)0.0056 (8)
C22A0.0513 (12)0.0530 (12)0.0473 (12)0.0114 (9)0.0002 (10)0.0034 (9)
C23A0.0408 (11)0.0656 (13)0.0359 (10)0.0077 (10)0.0033 (8)0.0049 (9)
C24A0.0416 (11)0.0628 (12)0.0381 (10)0.0166 (9)0.0042 (9)0.0091 (9)
C25A0.0381 (10)0.0425 (10)0.0412 (10)0.0073 (8)0.0052 (8)0.0060 (8)
C26A0.0538 (14)0.0992 (18)0.0604 (15)0.0087 (13)0.0141 (11)0.0078 (13)
O1B0.0582 (9)0.0345 (7)0.0584 (8)0.0059 (6)0.0040 (7)0.0056 (6)
O2B0.1059 (13)0.0372 (8)0.0651 (10)0.0171 (8)0.0196 (9)0.0074 (7)
N1B0.0529 (10)0.0583 (10)0.0469 (9)0.0208 (8)0.0168 (8)0.0150 (7)
N2B0.0500 (9)0.0386 (8)0.0484 (9)0.0038 (7)0.0005 (7)0.0179 (7)
N3B0.0490 (10)0.0617 (10)0.0578 (10)0.0179 (8)0.0191 (8)0.0291 (8)
C1B0.0439 (10)0.0350 (9)0.0410 (10)0.0079 (8)0.0101 (8)0.0112 (8)
C2B0.0479 (11)0.0342 (9)0.0373 (10)0.0120 (8)0.0086 (8)0.0102 (7)
C3B0.0583 (12)0.0354 (9)0.0398 (10)0.0108 (8)0.0121 (9)0.0123 (8)
C4B0.0592 (12)0.0426 (10)0.0416 (11)0.0130 (9)0.0130 (9)0.0104 (8)
C5B0.0937 (18)0.0727 (14)0.0555 (13)0.0257 (13)0.0365 (13)0.0159 (11)
C6B0.0813 (18)0.1004 (19)0.0769 (17)0.0328 (15)0.0398 (14)0.0149 (14)
C7B0.0665 (15)0.0865 (16)0.0767 (16)0.0340 (13)0.0300 (13)0.0213 (13)
C8B0.0415 (11)0.0352 (9)0.0469 (11)0.0091 (8)0.0053 (9)0.0095 (8)
C9B0.0399 (10)0.0464 (10)0.0422 (11)0.0049 (8)0.0079 (8)0.0103 (8)
C10B0.0530 (13)0.0693 (14)0.0446 (12)0.0042 (11)0.0040 (10)0.0145 (10)
C11B0.0521 (13)0.0817 (15)0.0444 (12)0.0024 (11)0.0055 (10)0.0002 (11)
C12B0.0544 (13)0.0588 (13)0.0595 (14)0.0108 (10)0.0143 (11)0.0039 (11)
C13B0.0550 (13)0.0455 (11)0.0582 (13)0.0009 (9)0.0154 (11)0.0099 (9)
C14B0.0400 (10)0.0397 (10)0.0450 (11)0.0048 (8)0.0108 (8)0.0083 (8)
C15B0.0585 (12)0.0419 (11)0.0464 (11)0.0181 (9)0.0076 (9)0.0081 (8)
C16B0.0859 (17)0.0659 (13)0.0453 (12)0.0325 (13)0.0209 (11)0.0093 (10)
C17B0.0719 (16)0.0869 (16)0.0587 (14)0.0377 (13)0.0309 (12)0.0301 (12)
C18B0.0459 (11)0.0479 (10)0.0472 (11)0.0151 (9)0.0088 (9)0.0184 (9)
C19B0.0526 (14)0.0855 (16)0.1029 (19)0.0141 (12)0.0219 (13)0.0549 (15)
C20B0.0634 (13)0.0493 (11)0.0388 (10)0.0196 (9)0.0148 (9)0.0188 (9)
C21B0.0896 (17)0.0579 (12)0.0470 (12)0.0306 (12)0.0081 (11)0.0134 (10)
C22B0.0951 (18)0.0806 (16)0.0556 (14)0.0522 (14)0.0231 (13)0.0296 (13)
C23B0.0687 (15)0.0930 (17)0.0403 (12)0.0336 (13)0.0196 (11)0.0271 (12)
C24B0.0677 (15)0.0778 (15)0.0450 (12)0.0162 (12)0.0088 (11)0.0121 (11)
C25B0.0693 (14)0.0551 (12)0.0467 (12)0.0189 (11)0.0087 (10)0.0119 (10)
C26B0.0811 (18)0.140 (2)0.0568 (15)0.0522 (17)0.0172 (13)0.0352 (15)
Geometric parameters (Å, º) top
O1A—C8A1.2244 (18)C26A—H26B0.9600
O2A—C15A1.2062 (19)C26A—H26C0.9600
N1A—C1A1.459 (2)O1B—C8B1.215 (2)
N1A—C7A1.464 (2)O2B—C15B1.208 (2)
N1A—C4A1.475 (2)N1B—C7B1.433 (3)
N2A—C8A1.346 (2)N1B—C4B1.439 (2)
N2A—C9A1.400 (2)N1B—C1B1.439 (2)
N2A—H2A0.8600N2B—C8B1.356 (2)
N3A—C17A1.443 (2)N2B—C9B1.398 (2)
N3A—C18A1.452 (2)N2B—H2B0.8600
N3A—C19A1.459 (2)N3B—C17B1.444 (3)
C1A—C14A1.527 (2)N3B—C18B1.454 (2)
C1A—C8A1.550 (2)N3B—C19B1.457 (3)
C1A—C2A1.586 (2)C1B—C14B1.508 (2)
C2A—C18A1.538 (2)C1B—C8B1.559 (2)
C2A—C15A1.539 (2)C1B—C2B1.616 (2)
C2A—C3A1.559 (2)C2B—C18B1.526 (2)
C3A—C20A1.517 (2)C2B—C15B1.527 (2)
C3A—C4A1.524 (2)C2B—C3B1.567 (2)
C3A—H3A0.9800C3B—C20B1.512 (3)
C4A—C5A1.519 (2)C3B—C4B1.514 (2)
C4A—H4A0.9800C3B—H3B0.9800
C5A—C6A1.414 (8)C4B—C5B1.516 (3)
C5A—C6AA1.526 (3)C4B—H4B0.9800
C5A—H51A0.9700C5B—C6B1.533 (3)
C5A—H52A0.9700C5B—H51B0.9700
C6AA—C7A1.498 (3)C5B—H52B0.9700
C6AA—H61A0.9700C6B—C7B1.517 (3)
C6AA—H62A0.9700C6B—H61B0.9700
C6A—C7A1.637 (9)C6B—H62B0.9700
C6A—H63A0.9700C7B—H71B0.9700
C6A—H64A0.9700C7B—H72B0.9700
C7A—H71A0.9700C9B—C10B1.377 (3)
C7A—H72A0.9700C9B—C14B1.391 (2)
C9A—C10A1.378 (2)C10B—C11B1.382 (3)
C9A—C14A1.387 (2)C10B—H10B0.9300
C10A—C11A1.382 (3)C11B—C12B1.375 (3)
C10A—H10A0.9300C11B—H11B0.9300
C11A—C12A1.375 (3)C12B—C13B1.383 (3)
C11A—H11A0.9300C12B—H12B0.9300
C12A—C13A1.389 (2)C13B—C14B1.379 (2)
C12A—H12A0.9300C13B—H13B0.9300
C13A—C14A1.382 (2)C15B—C16B1.501 (3)
C13A—H13A0.9300C16B—C17B1.516 (3)
C15A—C16A1.497 (2)C16B—H16C0.9700
C16A—C17A1.509 (3)C16B—H16D0.9700
C16A—H16A0.9700C17B—H17C0.9700
C16A—H16B0.9700C17B—H17D0.9700
C17A—H17A0.9700C18B—H18C0.9700
C17A—H17B0.9700C18B—H18D0.9700
C18A—H18A0.9700C19B—H19D0.9600
C18A—H18B0.9700C19B—H19E0.9600
C19A—H19A0.9600C19B—H19F0.9600
C19A—H19B0.9600C20B—C25B1.382 (3)
C19A—H19C0.9600C20B—C21B1.390 (3)
C20A—C25A1.385 (2)C21B—C22B1.383 (3)
C20A—C21A1.391 (2)C21B—H21B0.9300
C21A—C22A1.380 (3)C22B—C23B1.379 (3)
C21A—H21A0.9300C22B—H22B0.9300
C22A—C23A1.377 (3)C23B—C24B1.369 (3)
C22A—H22A0.9300C23B—C26B1.503 (3)
C23A—C24A1.378 (3)C24B—C25B1.384 (3)
C23A—C26A1.507 (3)C24B—H24B0.9300
C24A—C25A1.380 (2)C25B—H25B0.9300
C24A—H24A0.9300C26B—H26D0.9600
C25A—H25A0.9300C26B—H26E0.9600
C26A—H26A0.9600C26B—H26F0.9600
C1A—N1A—C7A118.87 (13)C23A—C26A—H26A109.5
C1A—N1A—C4A111.65 (12)C23A—C26A—H26B109.5
C7A—N1A—C4A108.84 (13)H26A—C26A—H26B109.5
C8A—N2A—C9A111.37 (14)C23A—C26A—H26C109.5
C8A—N2A—H2A124.3H26A—C26A—H26C109.5
C9A—N2A—H2A124.3H26B—C26A—H26C109.5
C17A—N3A—C18A111.02 (14)C7B—N1B—C4B108.59 (16)
C17A—N3A—C19A113.69 (16)C7B—N1B—C1B126.19 (15)
C18A—N3A—C19A112.65 (14)C4B—N1B—C1B111.17 (14)
N1A—C1A—C14A119.65 (13)C8B—N2B—C9B111.89 (14)
N1A—C1A—C8A106.99 (12)C8B—N2B—H2B124.1
C14A—C1A—C8A100.53 (12)C9B—N2B—H2B124.1
N1A—C1A—C2A102.75 (11)C17B—N3B—C18B109.34 (15)
C14A—C1A—C2A112.81 (12)C17B—N3B—C19B112.47 (17)
C8A—C1A—C2A114.51 (13)C18B—N3B—C19B111.71 (17)
C18A—C2A—C15A107.69 (13)N1B—C1B—C14B109.95 (14)
C18A—C2A—C3A114.06 (12)N1B—C1B—C8B113.05 (14)
C15A—C2A—C3A110.71 (12)C14B—C1B—C8B100.99 (13)
C18A—C2A—C1A110.80 (12)N1B—C1B—C2B101.40 (13)
C15A—C2A—C1A112.00 (12)C14B—C1B—C2B118.35 (14)
C3A—C2A—C1A101.60 (12)C8B—C1B—C2B113.55 (14)
C20A—C3A—C4A114.31 (13)C18B—C2B—C15B107.40 (15)
C20A—C3A—C2A116.31 (13)C18B—C2B—C3B111.75 (14)
C4A—C3A—C2A104.97 (12)C15B—C2B—C3B112.54 (13)
C20A—C3A—H3A106.9C18B—C2B—C1B112.55 (13)
C4A—C3A—H3A106.9C15B—C2B—C1B109.27 (14)
C2A—C3A—H3A106.9C3B—C2B—C1B103.38 (13)
N1A—C4A—C5A105.27 (13)C20B—C3B—C4B116.77 (15)
N1A—C4A—C3A105.94 (12)C20B—C3B—C2B117.33 (15)
C5A—C4A—C3A118.54 (14)C4B—C3B—C2B102.11 (13)
N1A—C4A—H4A108.9C20B—C3B—H3B106.6
C5A—C4A—H4A108.9C4B—C3B—H3B106.6
C3A—C4A—H4A108.9C2B—C3B—H3B106.6
C6A—C5A—C4A109.8 (3)N1B—C4B—C3B100.22 (14)
C4A—C5A—C6AA101.44 (16)N1B—C4B—C5B100.92 (16)
C6A—C5A—H51A135.8C3B—C4B—C5B122.04 (15)
C4A—C5A—H51A111.5N1B—C4B—H4B110.8
C6AA—C5A—H51A111.5C3B—C4B—H4B110.8
C6A—C5A—H52A68.2C5B—C4B—H4B110.8
C4A—C5A—H52A111.5C4B—C5B—C6B103.76 (17)
C6AA—C5A—H52A111.5C4B—C5B—H51B111.0
H51A—C5A—H52A109.3C6B—C5B—H51B111.0
C7A—C6AA—C5A103.1 (2)C4B—C5B—H52B111.0
C7A—C6AA—H61A111.2C6B—C5B—H52B111.0
C5A—C6AA—H61A111.2H51B—C5B—H52B109.0
C7A—C6AA—H62A111.2C7B—C6B—C5B106.14 (18)
C5A—C6AA—H62A111.2C7B—C6B—H61B110.5
H61A—C6AA—H62A109.1C5B—C6B—H61B110.5
C5A—C6A—C7A101.6 (5)C7B—C6B—H62B110.5
C5A—C6A—H63A111.5C5B—C6B—H62B110.5
C7A—C6A—H63A111.5H61B—C6B—H62B108.7
C5A—C6A—H64A111.5N1B—C7B—C6B102.28 (18)
C7A—C6A—H64A111.5N1B—C7B—H71B111.3
H63A—C6A—H64A109.3C6B—C7B—H71B111.3
N1A—C7A—C6AA105.09 (16)N1B—C7B—H72B111.3
N1A—C7A—C6A101.9 (3)C6B—C7B—H72B111.3
N1A—C7A—H71A110.7H71B—C7B—H72B109.2
C6AA—C7A—H71A110.7O1B—C8B—N2B125.57 (15)
C6A—C7A—H71A74.1O1B—C8B—C1B125.97 (15)
N1A—C7A—H72A110.7N2B—C8B—C1B108.10 (14)
C6AA—C7A—H72A110.7C10B—C9B—C14B121.75 (17)
C6A—C7A—H72A142.8C10B—C9B—N2B128.76 (16)
H71A—C7A—H72A108.8C14B—C9B—N2B109.38 (15)
O1A—C8A—N2A125.70 (15)C9B—C10B—C11B117.42 (18)
O1A—C8A—C1A125.42 (14)C9B—C10B—H10B121.3
N2A—C8A—C1A108.55 (13)C11B—C10B—H10B121.3
C10A—C9A—C14A122.37 (16)C12B—C11B—C10B121.77 (19)
C10A—C9A—N2A127.68 (16)C12B—C11B—H11B119.1
C14A—C9A—N2A109.93 (13)C10B—C11B—H11B119.1
C9A—C10A—C11A117.75 (18)C11B—C12B—C13B120.26 (19)
C9A—C10A—H10A121.1C11B—C12B—H12B119.9
C11A—C10A—H10A121.1C13B—C12B—H12B119.9
C12A—C11A—C10A120.92 (17)C14B—C13B—C12B119.10 (18)
C12A—C11A—H11A119.5C14B—C13B—H13B120.5
C10A—C11A—H11A119.5C12B—C13B—H13B120.5
C11A—C12A—C13A120.87 (17)C13B—C14B—C9B119.69 (17)
C11A—C12A—H12A119.6C13B—C14B—C1B130.42 (16)
C13A—C12A—H12A119.6C9B—C14B—C1B109.56 (14)
C14A—C13A—C12A118.96 (17)O2B—C15B—C16B121.35 (17)
C14A—C13A—H13A120.5O2B—C15B—C2B122.23 (17)
C12A—C13A—H13A120.5C16B—C15B—C2B116.42 (16)
C13A—C14A—C9A119.12 (15)C15B—C16B—C17B113.12 (17)
C13A—C14A—C1A132.36 (15)C15B—C16B—H16C109.0
C9A—C14A—C1A108.51 (13)C17B—C16B—H16C109.0
O2A—C15A—C16A120.55 (15)C15B—C16B—H16D109.0
O2A—C15A—C2A121.80 (15)C17B—C16B—H16D109.0
C16A—C15A—C2A117.62 (15)H16C—C16B—H16D107.8
C15A—C16A—C17A112.37 (15)N3B—C17B—C16B110.04 (17)
C15A—C16A—H16A109.1N3B—C17B—H17C109.7
C17A—C16A—H16A109.1C16B—C17B—H17C109.7
C15A—C16A—H16B109.1N3B—C17B—H17D109.7
C17A—C16A—H16B109.1C16B—C17B—H17D109.7
H16A—C16A—H16B107.9H17C—C17B—H17D108.2
N3A—C17A—C16A108.98 (15)N3B—C18B—C2B110.83 (14)
N3A—C17A—H17A109.9N3B—C18B—H18C109.5
C16A—C17A—H17A109.9C2B—C18B—H18C109.5
N3A—C17A—H17B109.9N3B—C18B—H18D109.5
C16A—C17A—H17B109.9C2B—C18B—H18D109.5
H17A—C17A—H17B108.3H18C—C18B—H18D108.1
N3A—C18A—C2A110.66 (13)N3B—C19B—H19D109.5
N3A—C18A—H18A109.5N3B—C19B—H19E109.5
C2A—C18A—H18A109.5H19D—C19B—H19E109.5
N3A—C18A—H18B109.5N3B—C19B—H19F109.5
C2A—C18A—H18B109.5H19D—C19B—H19F109.5
H18A—C18A—H18B108.1H19E—C19B—H19F109.5
N3A—C19A—H19A109.5C25B—C20B—C21B117.16 (18)
N3A—C19A—H19B109.5C25B—C20B—C3B122.95 (17)
H19A—C19A—H19B109.5C21B—C20B—C3B119.81 (18)
N3A—C19A—H19C109.5C22B—C21B—C20B120.7 (2)
H19A—C19A—H19C109.5C22B—C21B—H21B119.6
H19B—C19A—H19C109.5C20B—C21B—H21B119.6
C25A—C20A—C21A116.76 (15)C23B—C22B—C21B121.8 (2)
C25A—C20A—C3A122.63 (14)C23B—C22B—H22B119.1
C21A—C20A—C3A120.58 (14)C21B—C22B—H22B119.1
C22A—C21A—C20A121.06 (17)C24B—C23B—C22B117.3 (2)
C22A—C21A—H21A119.5C24B—C23B—C26B121.6 (2)
C20A—C21A—H21A119.5C22B—C23B—C26B121.0 (2)
C23A—C22A—C21A121.99 (18)C23B—C24B—C25B121.6 (2)
C23A—C22A—H22A119.0C23B—C24B—H24B119.2
C21A—C22A—H22A119.0C25B—C24B—H24B119.2
C22A—C23A—C24A116.99 (17)C20B—C25B—C24B121.4 (2)
C22A—C23A—C26A122.42 (19)C20B—C25B—H25B119.3
C24A—C23A—C26A120.57 (19)C24B—C25B—H25B119.3
C23A—C24A—C25A121.64 (17)C23B—C26B—H26D109.5
C23A—C24A—H24A119.2C23B—C26B—H26E109.5
C25A—C24A—H24A119.2H26D—C26B—H26E109.5
C24A—C25A—C20A121.56 (16)C23B—C26B—H26F109.5
C24A—C25A—H25A119.2H26D—C26B—H26F109.5
C20A—C25A—H25A119.2H26E—C26B—H26F109.5
C7A—N1A—C1A—C14A27.6 (2)C22A—C23A—C24A—C25A0.1 (3)
C4A—N1A—C1A—C14A100.38 (15)C26A—C23A—C24A—C25A178.62 (19)
C7A—N1A—C1A—C8A85.58 (16)C23A—C24A—C25A—C20A0.3 (3)
C4A—N1A—C1A—C8A146.43 (12)C21A—C20A—C25A—C24A0.1 (3)
C7A—N1A—C1A—C2A153.49 (13)C3A—C20A—C25A—C24A177.76 (16)
C4A—N1A—C1A—C2A25.50 (15)C7B—N1B—C1B—C14B71.1 (2)
N1A—C1A—C2A—C18A86.50 (14)C4B—N1B—C1B—C14B153.96 (14)
C14A—C1A—C2A—C18A143.31 (13)C7B—N1B—C1B—C8B41.0 (3)
C8A—C1A—C2A—C18A29.13 (17)C4B—N1B—C1B—C8B94.02 (17)
N1A—C1A—C2A—C15A153.23 (13)C7B—N1B—C1B—C2B162.89 (19)
C14A—C1A—C2A—C15A23.04 (18)C4B—N1B—C1B—C2B27.91 (17)
C8A—C1A—C2A—C15A91.14 (15)N1B—C1B—C2B—C18B119.23 (15)
N1A—C1A—C2A—C3A35.05 (13)C14B—C1B—C2B—C18B120.48 (16)
C14A—C1A—C2A—C3A95.14 (14)C8B—C1B—C2B—C18B2.3 (2)
C8A—C1A—C2A—C3A150.67 (12)N1B—C1B—C2B—C15B121.54 (15)
C18A—C2A—C3A—C20A40.86 (18)C14B—C1B—C2B—C15B1.3 (2)
C15A—C2A—C3A—C20A80.78 (16)C8B—C1B—C2B—C15B116.88 (16)
C1A—C2A—C3A—C20A160.11 (12)N1B—C1B—C2B—C3B1.51 (16)
C18A—C2A—C3A—C4A86.55 (15)C14B—C1B—C2B—C3B118.78 (15)
C15A—C2A—C3A—C4A151.80 (13)C8B—C1B—C2B—C3B123.09 (15)
C1A—C2A—C3A—C4A32.70 (14)C18B—C2B—C3B—C20B35.3 (2)
C1A—N1A—C4A—C5A121.48 (14)C15B—C2B—C3B—C20B85.67 (19)
C7A—N1A—C4A—C5A11.69 (17)C1B—C2B—C3B—C20B156.56 (15)
C1A—N1A—C4A—C3A4.89 (16)C18B—C2B—C3B—C4B93.74 (17)
C7A—N1A—C4A—C3A138.07 (13)C15B—C2B—C3B—C4B145.32 (15)
C20A—C3A—C4A—N1A147.06 (13)C1B—C2B—C3B—C4B27.55 (16)
C2A—C3A—C4A—N1A18.44 (15)C7B—N1B—C4B—C3B170.33 (16)
C20A—C3A—C4A—C5A95.09 (17)C1B—N1B—C4B—C3B46.70 (17)
C2A—C3A—C4A—C5A136.29 (15)C7B—N1B—C4B—C5B44.6 (2)
N1A—C4A—C5A—C6A13.3 (5)C1B—N1B—C4B—C5B172.42 (14)
C3A—C4A—C5A—C6A104.9 (5)C20B—C3B—C4B—N1B172.76 (15)
N1A—C4A—C5A—C6AA31.8 (2)C2B—C3B—C4B—N1B43.40 (16)
C3A—C4A—C5A—C6AA150.0 (2)C20B—C3B—C4B—C5B77.4 (2)
C6A—C5A—C6AA—C7A66.6 (5)C2B—C3B—C4B—C5B153.27 (18)
C4A—C5A—C6AA—C7A40.2 (3)N1B—C4B—C5B—C6B32.1 (2)
C4A—C5A—C6A—C7A29.4 (6)C3B—C4B—C5B—C6B141.6 (2)
C6AA—C5A—C6A—C7A56.6 (5)C4B—C5B—C6B—C7B11.0 (3)
C1A—N1A—C7A—C6AA143.2 (2)C4B—N1B—C7B—C6B37.4 (2)
C4A—N1A—C7A—C6AA13.9 (2)C1B—N1B—C7B—C6B173.35 (19)
C1A—N1A—C7A—C6A101.0 (4)C5B—C6B—C7B—N1B14.6 (3)
C4A—N1A—C7A—C6A28.3 (4)C9B—N2B—C8B—O1B170.51 (18)
C5A—C6AA—C7A—N1A33.8 (3)C9B—N2B—C8B—C1B2.9 (2)
C5A—C6AA—C7A—C6A57.0 (4)N1B—C1B—C8B—O1B53.8 (2)
C5A—C6A—C7A—N1A35.3 (6)C14B—C1B—C8B—O1B171.20 (18)
C5A—C6A—C7A—C6AA64.2 (5)C2B—C1B—C8B—O1B61.0 (2)
C9A—N2A—C8A—O1A163.96 (16)N1B—C1B—C8B—N2B119.57 (16)
C9A—N2A—C8A—C1A9.70 (19)C14B—C1B—C8B—N2B2.15 (18)
N1A—C1A—C8A—O1A37.5 (2)C2B—C1B—C8B—N2B125.61 (15)
C14A—C1A—C8A—O1A163.20 (16)C8B—N2B—C9B—C10B173.85 (19)
C2A—C1A—C8A—O1A75.6 (2)C8B—N2B—C9B—C14B2.4 (2)
N1A—C1A—C8A—N2A136.14 (14)C14B—C9B—C10B—C11B1.5 (3)
C14A—C1A—C8A—N2A10.48 (16)N2B—C9B—C10B—C11B174.38 (19)
C2A—C1A—C8A—N2A110.73 (15)C9B—C10B—C11B—C12B0.5 (3)
C8A—N2A—C9A—C10A174.03 (18)C10B—C11B—C12B—C13B0.3 (3)
C8A—N2A—C9A—C14A4.5 (2)C11B—C12B—C13B—C14B0.1 (3)
C14A—C9A—C10A—C11A0.9 (3)C12B—C13B—C14B—C9B0.9 (3)
N2A—C9A—C10A—C11A177.47 (18)C12B—C13B—C14B—C1B173.48 (18)
C9A—C10A—C11A—C12A0.6 (3)C10B—C9B—C14B—C13B1.7 (3)
C10A—C11A—C12A—C13A0.3 (3)N2B—C9B—C14B—C13B174.85 (17)
C11A—C12A—C13A—C14A0.9 (3)C10B—C9B—C14B—C1B175.73 (17)
C12A—C13A—C14A—C9A0.7 (3)N2B—C9B—C14B—C1B0.9 (2)
C12A—C13A—C14A—C1A179.14 (17)N1B—C1B—C14B—C13B52.7 (2)
C10A—C9A—C14A—C13A0.3 (3)C8B—C1B—C14B—C13B172.39 (19)
N2A—C9A—C14A—C13A178.37 (15)C2B—C1B—C14B—C13B63.0 (3)
C10A—C9A—C14A—C1A178.56 (16)N1B—C1B—C14B—C9B120.42 (16)
N2A—C9A—C14A—C1A2.82 (19)C8B—C1B—C14B—C9B0.75 (18)
N1A—C1A—C14A—C13A57.0 (2)C2B—C1B—C14B—C9B123.81 (16)
C8A—C1A—C14A—C13A173.61 (18)C18B—C2B—C15B—O2B136.52 (19)
C2A—C1A—C14A—C13A64.0 (2)C3B—C2B—C15B—O2B13.1 (3)
N1A—C1A—C14A—C9A124.40 (15)C1B—C2B—C15B—O2B101.1 (2)
C8A—C1A—C14A—C9A7.79 (17)C18B—C2B—C15B—C16B43.8 (2)
C2A—C1A—C14A—C9A114.62 (15)C3B—C2B—C15B—C16B167.16 (16)
C18A—C2A—C15A—O2A136.59 (16)C1B—C2B—C15B—C16B78.6 (2)
C3A—C2A—C15A—O2A11.3 (2)O2B—C15B—C16B—C17B139.0 (2)
C1A—C2A—C15A—O2A101.35 (18)C2B—C15B—C16B—C17B41.3 (2)
C18A—C2A—C15A—C16A41.64 (19)C18B—N3B—C17B—C16B63.3 (2)
C3A—C2A—C15A—C16A166.96 (14)C19B—N3B—C17B—C16B172.04 (16)
C1A—C2A—C15A—C16A80.42 (18)C15B—C16B—C17B—N3B49.1 (2)
O2A—C15A—C16A—C17A136.01 (18)C17B—N3B—C18B—C2B69.51 (19)
C2A—C15A—C16A—C17A42.2 (2)C19B—N3B—C18B—C2B165.34 (16)
C18A—N3A—C17A—C16A65.47 (19)C15B—C2B—C18B—N3B56.88 (18)
C19A—N3A—C17A—C16A166.27 (16)C3B—C2B—C18B—N3B179.24 (14)
C15A—C16A—C17A—N3A51.2 (2)C1B—C2B—C18B—N3B63.43 (19)
C17A—N3A—C18A—C2A67.97 (18)C4B—C3B—C20B—C25B19.5 (3)
C19A—N3A—C18A—C2A163.22 (15)C2B—C3B—C20B—C25B102.2 (2)
C15A—C2A—C18A—N3A52.32 (17)C4B—C3B—C20B—C21B157.21 (18)
C3A—C2A—C18A—N3A175.61 (13)C2B—C3B—C20B—C21B81.1 (2)
C1A—C2A—C18A—N3A70.49 (16)C25B—C20B—C21B—C22B0.4 (3)
C4A—C3A—C20A—C25A36.6 (2)C3B—C20B—C21B—C22B177.25 (19)
C2A—C3A—C20A—C25A86.09 (19)C20B—C21B—C22B—C23B0.5 (3)
C4A—C3A—C20A—C21A141.23 (16)C21B—C22B—C23B—C24B0.2 (3)
C2A—C3A—C20A—C21A96.12 (18)C21B—C22B—C23B—C26B179.6 (2)
C25A—C20A—C21A—C22A0.2 (3)C22B—C23B—C24B—C25B0.2 (3)
C3A—C20A—C21A—C22A178.11 (17)C26B—C23B—C24B—C25B179.9 (2)
C20A—C21A—C22A—C23A0.4 (3)C21B—C20B—C25B—C24B0.0 (3)
C21A—C22A—C23A—C24A0.2 (3)C3B—C20B—C25B—C24B176.80 (18)
C21A—C22A—C23A—C26A178.3 (2)C23B—C24B—C25B—C20B0.3 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C20A–C25A and C20B–C25B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1Ai0.861.992.8331 (17)167
N2B—H2B···O1Aii0.862.483.0829 (18)128
N2B—H2B···N1Aii0.862.243.0461 (18)156
C4A—H4A···O1Biii0.982.523.4598 (19)160
C16B—H16C···O2A0.972.473.431 (2)171
C5A—H52A···O2B0.972.583.404 (2)143
C6A—H63A···Cg1iv0.972.973.819 (9)147
C6B—H62B···Cg2iv0.972.933.827 (3)155
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y1, z; (iii) x, y+1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H29N3O2
Mr415.52
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7516 (4), 12.4649 (5), 21.4605 (8)
α, β, γ (°)97.654 (2), 101.024 (2), 102.345 (2)
V3)2207.45 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.28 × 0.19 × 0.19
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.93, 0.96
No. of measured, independent and
observed [I > 2σ(I)] reflections
44464, 7765, 5493
Rint0.037
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.110, 1.02
No. of reflections7765
No. of parameters574
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

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

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C20A–C25A and C20B–C25B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1Ai0.861.992.8331 (17)167
N2B—H2B···O1Aii0.862.483.0829 (18)128
N2B—H2B···N1Aii0.862.243.0461 (18)156
C4A—H4A···O1Biii0.982.523.4598 (19)160
C16B—H16C···O2A0.972.473.431 (2)171
C5A—H52A···O2B0.972.583.404 (2)143
C6A—H63A···Cg1iv0.972.973.819 (9)147
C6B—H62B···Cg2iv0.972.933.827 (3)155
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y1, z; (iii) x, y+1, z; (iv) x+1, y, z.
 

Acknowledgements

The authors thank the Sophisticated Analytical Instrumentation Facility (SAIF), Indian Institute of Technology, Chennai, for the X-ray intensity data collection.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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Volume 68| Part 9| September 2012| Pages o2772-o2773
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