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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Pages o113-o114
https://doi.org/10.1107/S1600536810050737

N-(9,11-Dimeth­­oxy-4-oxo-2,3,4,6,7,11b-hexa­hydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide

Hoong-Kun Fun,a*‡ Punlop Kuntiyong,b Pittaya Tuntiwachwuttikulb and Suchada Chantraprommac§

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Faculty of Science, Silpakorn University, Rajamanka Nai Road, Muang Nakhon Pathom 73000, Thailand, and cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my

(Received 24 November 2010; accepted 3 December 2010; online 11 December 2010)

The title schulzeine derivative, C22H24N2O4, crystallizes with two crystallographically independent mol­ecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetra­hydro­isoquinoline and δ-lactam moieties. In both mol­ecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation. The two meth­oxy groups are slightly twisted from the attached benzene ring [C—O—C—C torsion angles = −21.3 (2) and −20.5 (2)° in mol­ecule A, and −6.3 (2) and −16.2 (2)° in mol­ecule B] and the benzamide moiety is in a (−)-synclinal conformation with respect to the lactam ring. In the crystal, mol­ecules are linked into V-shaped dimers by inter­molecular N—H⋯O hydrogen bonds and weak C—H⋯O inter­actions. These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked in an anti­parallel manner. C—H⋯π inter­actions are also observed.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For background to schulzeines, see, for example: Kuntiyong et al. (2006[Kuntiyong, P., Akkarasmiyo, S. & Eksinitkun, G. (2006). Chem. Lett. 35, 1008-1009.]); Melo et al. (2006[Melo, E. B., Gomes, A. S. & Carvalho, I. (2006). Tetrahedron, 62, 10277-10302.]); Takada et al. (2004)[Takada, K., Uehara, T., Nakao, Y., Matsunaga, S., van Soest, R. W. M. & Fusetani, N. (2004). J. Am. Chem. Soc. 126, 187-193.]. For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986)[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.].

[Scheme 1]

Experimental

Crystal data

  • C22H24N2O4

  • Mr = 380.43

  • Orthorhombic, P 21 21 21

  • a = 12.6530 (3) Å

  • b = 15.5256 (4) Å

  • c = 19.7819 (5) Å

  • V = 3886.06 (17) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.56 × 0.44 × 0.41 mm
Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.964

  • 110999 measured reflections

  • 6224 independent reflections

  • 5979 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.04

  • 6224 reflections

  • 509 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A–C6A and C15A–C20A benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2AA⋯O1Bi 0.86 2.08 2.8994 (18) 158
N2B—H2BA⋯O1Aii 0.86 2.24 2.9807 (18) 145
C1A—H1AA⋯O4Biii 0.93 2.52 3.405 (2) 160
C10A—H10B⋯O3A 0.97 2.58 3.127 (2) 115
C3B—H3BA⋯O4Aiv 0.93 2.49 3.348 (2) 153
C7B—H7BB⋯O4Av 0.97 2.47 3.407 (2) 163
C16A—H16A⋯O1Bi 0.93 2.32 3.228 (2) 165
C20B—H20B⋯O1Aii 0.93 2.51 3.281 (2) 141
C22A—H22A⋯O2Aiv 0.96 2.52 3.266 (2) 135
C22A—H22B⋯O4Bvi 0.96 2.47 3.393 (2) 160
C22B—H22D⋯O4Aiv 0.96 2.58 3.414 (2) 146
C11A—H11B⋯Cg2ii 0.97 2.78 3.686 (2) 156
C8B—H8BA⋯Cg1iv 0.97 2.60 3.4864 (17) 152
C18B—H18B⋯Cg1i 0.93 2.81 3.607 (2) 144
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iii) x, y+1, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x+1, y, z; (vi) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050737/rz2531sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050737/rz2531Isup2.hkl

checkCIF report


Comment top

Schulzeine alkaloids were isolated from the marine sponge Penares schulzei (Takada et al., 2004). Schulzenine A—C inhibits α-glucosidase with IC50 values of 48–170 nM (Melo et al., 2006). The potent α-glucosidase inhibitory activity makes them attractive leads for drug candidate for diseases such as cancer, diabetes and viral infections. During the course of our research on natural product synthesis of schulzeines, the title schulzeine benzamide derivative was synthesized (Kuntiyong et al., 2006). The single-crystal x-ray structural study of the title compound (I) was undertaken in order to gain detailed conformations of the molecular structure.

The title compound crystallized with two crystallographically independent molecues A and B in the asymmetric unit (Fig. 1). These two molecules are almost conformationally identical with slightly different bond lengths and angles. The bond lengths in (I) are within normal ranges (Allen et al., 1987). The tricyclic core of schulzeine (C1–C13/N1/O1) has a fused-three-ring system comprising of the tetrahydro isoquinoline and δ-lactam moieties. In both molecules, the pyridine ring (C5–C9/N1) adopts a twisted boat conformation with puckering parameters Q = 0.6943 (17) Å, θ = 92.19 (14)° and φ = 245.21 (14)° in molecule A [Q = 0.5265 (16) Å, θ = 112.63 (17)° and φ = 263.90 (19)° in molecule B] and the lactam ring (C9–C13/N1/O1) has a standard boat conformation (Cremer & Pople 1975). The two methoxy groups are slightly twisted from the attached benzene ring with the torsion angles C21–O2–C2–C3 = -21.3 (2)° and C22–O3–C4–C3 = -20.5 (2)° in molecule A [the corresponding values are -6.3 (2) and -16.2 (2)° in molecule B]. The benzamide moiety is not planar with the dihedral angle between the mean plane through C14–C15/N2/O4 and C15–C20 benzene ring being 8.97 (9)° in molecule A [8.10 (11)° in molecule B]. The orientation of the benzamide moiety can be described by the torsion angle C14–N2–C12–C13 = -92.77 (17)° in molecule A [-82.56 (18)° in molecule B] which shows the (-)-syn-clinal conformation with respect to the lactam ring. There are two stereogenic centers at atoms C12 and C9 (Fig. 1) or postions 3 and 11b of the tricyclic core of schulzeine. Fig. 1 show that H atoms at C12 and C9 are in cis-relationship. An intramolecular C10A—H10B···O3A weak interaction (Table 1; Fig. 1) generates a S(6) ring motif (Bernstein et al., 1995).

In the crystal packing (Fig. 2), molecules are linked into V-shaped dimers by N—H···O hydrogen bonds and C—H···O weak interactions (Table 1) which generate two S(7) ring motifs (Bernstein et al., 1995). These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked by C—H···O weak interactions in an antiparallel manner. C—H···π interactions were also observed (Table 1); Cg1 and Cg2 are the centroid of C1A–C6A and C15A–C20A benzene rings, respectively.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For background to schulzeines, see, for example: Kuntiyong et al. (2006); Melo et al. (2006); Takada et al. (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title schulzeine benzamide derivative was synthesized according to the previous reported method (Kuntiyong et al., 2006). Colourless block-shaped single crystals of the title compound suitable for x-ray structure determination were crystallized from hexane:ethylacetate (2:1 v/v) by slow evaporation at room temperature after a few days.

Refinement top

All H atoms were placed in calculated positions with d(N—H) = 0.86 Å, d(C—H) = 0.93 Å for aromatic, 0.97 for CH2 and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 2.33 Å from H21G and the deepest hole is located at 1.38 Å from C5B. A total of 5097 Friedel pairs were merged before final refinement as there is no large anomalous dispersion for the determination of the absolute configuration.

Structure description top

Schulzeine alkaloids were isolated from the marine sponge Penares schulzei (Takada et al., 2004). Schulzenine A—C inhibits α-glucosidase with IC50 values of 48–170 nM (Melo et al., 2006). The potent α-glucosidase inhibitory activity makes them attractive leads for drug candidate for diseases such as cancer, diabetes and viral infections. During the course of our research on natural product synthesis of schulzeines, the title schulzeine benzamide derivative was synthesized (Kuntiyong et al., 2006). The single-crystal x-ray structural study of the title compound (I) was undertaken in order to gain detailed conformations of the molecular structure.

The title compound crystallized with two crystallographically independent molecues A and B in the asymmetric unit (Fig. 1). These two molecules are almost conformationally identical with slightly different bond lengths and angles. The bond lengths in (I) are within normal ranges (Allen et al., 1987). The tricyclic core of schulzeine (C1–C13/N1/O1) has a fused-three-ring system comprising of the tetrahydro isoquinoline and δ-lactam moieties. In both molecules, the pyridine ring (C5–C9/N1) adopts a twisted boat conformation with puckering parameters Q = 0.6943 (17) Å, θ = 92.19 (14)° and φ = 245.21 (14)° in molecule A [Q = 0.5265 (16) Å, θ = 112.63 (17)° and φ = 263.90 (19)° in molecule B] and the lactam ring (C9–C13/N1/O1) has a standard boat conformation (Cremer & Pople 1975). The two methoxy groups are slightly twisted from the attached benzene ring with the torsion angles C21–O2–C2–C3 = -21.3 (2)° and C22–O3–C4–C3 = -20.5 (2)° in molecule A [the corresponding values are -6.3 (2) and -16.2 (2)° in molecule B]. The benzamide moiety is not planar with the dihedral angle between the mean plane through C14–C15/N2/O4 and C15–C20 benzene ring being 8.97 (9)° in molecule A [8.10 (11)° in molecule B]. The orientation of the benzamide moiety can be described by the torsion angle C14–N2–C12–C13 = -92.77 (17)° in molecule A [-82.56 (18)° in molecule B] which shows the (-)-syn-clinal conformation with respect to the lactam ring. There are two stereogenic centers at atoms C12 and C9 (Fig. 1) or postions 3 and 11b of the tricyclic core of schulzeine. Fig. 1 show that H atoms at C12 and C9 are in cis-relationship. An intramolecular C10A—H10B···O3A weak interaction (Table 1; Fig. 1) generates a S(6) ring motif (Bernstein et al., 1995).

In the crystal packing (Fig. 2), molecules are linked into V-shaped dimers by N—H···O hydrogen bonds and C—H···O weak interactions (Table 1) which generate two S(7) ring motifs (Bernstein et al., 1995). These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked by C—H···O weak interactions in an antiparallel manner. C—H···π interactions were also observed (Table 1); Cg1 and Cg2 are the centroid of C1A–C6A and C15A–C20A benzene rings, respectively.

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For background to schulzeines, see, for example: Kuntiyong et al. (2006); Melo et al. (2006); Takada et al. (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. The intramolecular C—H···O weak interaction is shown as dash line.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.
N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H- pyrido[2,1-a]isoquinolin-3-yl)benzamide top
Crystal data top
C22H24N2O4F(000) = 1616
Mr = 380.43Dx = 1.301 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6224 reflections
a = 12.6530 (3) Åθ = 1.7–30.0°
b = 15.5256 (4) ŵ = 0.09 mm−1
c = 19.7819 (5) ÅT = 100 K
V = 3886.06 (17) Å3Block, colourless
Z = 80.56 × 0.44 × 0.41 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer		6224 independent reflections
Radiation source: fine-focus sealed tube5979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.7°
ω scansh = −17→17
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −21→21
Tmin = 0.952, Tmax = 0.964l = −27→27
110999 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.8464P]
where P = (Fo2 + 2Fc2)/3
6224 reflections(Δ/σ)max = 0.001
509 parametersΔρmax = 0.60 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C22H24N2O4V = 3886.06 (17) Å3
Mr = 380.43Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 12.6530 (3) ŵ = 0.09 mm−1
b = 15.5256 (4) ÅT = 100 K
c = 19.7819 (5) Å0.56 × 0.44 × 0.41 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer		6224 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5979 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.964Rint = 0.044
110999 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.60 e Å−3
6224 reflectionsΔρmin = −0.21 e Å−3
509 parameters
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A−0.02471 (9)1.04124 (8)0.08332 (6)0.0221 (2)
O2A0.57498 (10)1.20708 (8)0.23122 (7)0.0271 (3)
O3A0.41894 (9)0.92533 (8)0.19545 (6)0.0199 (2)
O4A−0.09182 (10)0.81182 (8)0.13037 (6)0.0216 (2)
N1A0.14296 (10)1.04299 (9)0.12475 (7)0.0175 (2)
N2A−0.01509 (11)0.87770 (10)0.04098 (7)0.0187 (3)
H2AA−0.01590.8832−0.00230.022*
C1A0.41044 (14)1.19103 (11)0.17940 (8)0.0213 (3)
H1AA0.40821.25060.17450.026*
C2A0.49678 (13)1.15230 (11)0.20998 (8)0.0206 (3)
C3A0.50218 (12)1.06320 (11)0.21678 (8)0.0187 (3)
H3AA0.56001.03730.23750.022*
C4A0.41891 (12)1.01348 (10)0.19180 (8)0.0166 (3)
C5A0.32962 (12)1.05092 (10)0.16217 (7)0.0163 (3)
C6A0.32713 (13)1.14081 (11)0.15601 (8)0.0187 (3)
C7A0.23051 (14)1.18307 (11)0.12658 (9)0.0222 (3)
H7AA0.23611.18480.07770.027*
H7AB0.22501.24180.14300.027*
C8A0.13342 (13)1.13264 (11)0.14688 (9)0.0209 (3)
H8AA0.12521.13460.19560.025*
H8AB0.07121.15840.12660.025*
C9A0.24112 (12)0.99366 (10)0.13682 (7)0.0158 (3)
H9AA0.22680.94950.17100.019*
C10A0.27105 (13)0.94854 (11)0.07015 (8)0.0189 (3)
H10A0.29250.99160.03740.023*
H10B0.33090.91080.07810.023*
C11A0.17958 (13)0.89550 (12)0.04059 (8)0.0212 (3)
H11A0.16960.9114−0.00640.025*
H11B0.19820.83490.04200.025*
C12A0.07537 (12)0.90884 (11)0.07883 (8)0.0170 (3)
H12A0.07920.87660.12130.020*
C13A0.05917 (12)1.00405 (11)0.09583 (7)0.0174 (3)
C14A−0.09814 (12)0.84027 (10)0.07226 (8)0.0166 (3)
C15A−0.20086 (12)0.83599 (10)0.03375 (8)0.0166 (3)
C16A−0.21118 (14)0.86011 (13)−0.03395 (9)0.0257 (4)
H16A−0.15190.8769−0.05840.031*
C17A−0.30990 (15)0.85908 (14)−0.06489 (9)0.0292 (4)
H17A−0.31630.8755−0.10990.035*
C18A−0.39848 (14)0.83383 (12)−0.02912 (9)0.0249 (3)
H18A−0.46420.8330−0.05010.030*
C19A−0.38905 (13)0.80972 (12)0.03818 (9)0.0224 (3)
H19A−0.44860.79270.06230.027*
C20A−0.29063 (13)0.81098 (10)0.06949 (8)0.0186 (3)
H20A−0.28470.79500.11460.022*
C21A0.64678 (16)1.17622 (14)0.28122 (12)0.0334 (4)
H21A0.68891.22320.29760.050*
H21B0.69201.13330.26170.050*
H21C0.60781.15140.31800.050*
C22A0.51984 (13)0.88467 (11)0.20440 (9)0.0223 (3)
H22A0.51210.82340.19980.033*
H22B0.54660.89780.24860.033*
H22C0.56820.90560.17080.033*
O1B0.50160 (9)0.55662 (8)0.09581 (6)0.0203 (2)
O2B1.13487 (9)0.53207 (8)0.24302 (6)0.0230 (3)
O3B0.85002 (9)0.32332 (7)0.22556 (6)0.0209 (2)
O4B0.33646 (10)0.39884 (9)0.15123 (6)0.0241 (3)
N1B0.65877 (11)0.50975 (8)0.13713 (7)0.0159 (2)
N2B0.43821 (11)0.39672 (10)0.05729 (7)0.0193 (3)
H2BA0.44030.39130.01400.023*
C1B0.97678 (12)0.56373 (10)0.18722 (8)0.0167 (3)
H1BA1.00460.61770.17730.020*
C2B1.03665 (12)0.50468 (11)0.22370 (8)0.0174 (3)
C3B0.99674 (12)0.42308 (10)0.23801 (8)0.0170 (3)
H3BA1.03650.38340.26240.020*
C4B0.89549 (12)0.40221 (10)0.21479 (7)0.0153 (3)
C5B0.83320 (12)0.46120 (10)0.17890 (7)0.0150 (3)
C6B0.87571 (12)0.54239 (10)0.16559 (7)0.0153 (3)
C7B0.80872 (12)0.60788 (10)0.12956 (8)0.0176 (3)
H7BA0.81410.59970.08110.021*
H7BB0.83320.66550.14020.021*
C8B0.69425 (12)0.59717 (10)0.15200 (8)0.0171 (3)
H8BA0.68850.60810.20010.021*
H8BB0.64990.63830.12840.021*
C9B0.72515 (11)0.43407 (10)0.15402 (8)0.0146 (3)
H9BA0.69010.40130.18990.018*
C10B0.73405 (13)0.37627 (11)0.09087 (8)0.0198 (3)
H10C0.78150.40320.05870.024*
H10D0.76450.32140.10380.024*
C11B0.62681 (13)0.36037 (12)0.05659 (9)0.0222 (3)
H11C0.62900.38290.01090.027*
H11D0.61420.29880.05390.027*
C12B0.53572 (12)0.40287 (11)0.09492 (8)0.0168 (3)
H12B0.52650.37270.13800.020*
C13B0.56258 (12)0.49707 (10)0.10982 (7)0.0161 (3)
C14B0.34367 (12)0.39942 (10)0.08899 (8)0.0177 (3)
C15B0.24663 (12)0.39956 (11)0.04551 (8)0.0191 (3)
C16B0.15036 (14)0.41091 (14)0.07706 (10)0.0297 (4)
H16B0.14800.41800.12370.036*
C17B0.05695 (15)0.41197 (17)0.04015 (12)0.0377 (5)
H17B−0.00730.41990.06210.045*
C18B0.05931 (15)0.40119 (15)−0.02913 (11)0.0331 (4)
H18B−0.00300.4028−0.05400.040*
C19B0.15575 (16)0.38786 (17)−0.06142 (10)0.0381 (5)
H19B0.15760.3793−0.10790.046*
C20B0.24924 (15)0.38723 (16)−0.02456 (9)0.0316 (4)
H20B0.31340.3786−0.04640.038*
C21B1.19478 (14)0.47576 (13)0.28599 (10)0.0257 (4)
H21D1.25850.50420.30000.038*
H21G1.21240.42420.26170.038*
H21E1.15350.46120.32510.038*
C22B0.91795 (15)0.25465 (11)0.24549 (10)0.0246 (3)
H22G0.88060.20100.24220.037*
H22D0.94040.26350.29130.037*
H22E0.97860.25320.21640.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0152 (5)0.0286 (6)0.0224 (5)0.0016 (5)−0.0013 (4)0.0001 (5)
O2A0.0211 (6)0.0247 (6)0.0356 (7)−0.0071 (5)−0.0059 (5)−0.0060 (5)
O3A0.0150 (5)0.0189 (5)0.0257 (6)−0.0001 (4)−0.0024 (4)0.0005 (4)
O4A0.0216 (6)0.0264 (6)0.0167 (5)−0.0076 (5)−0.0026 (4)0.0036 (4)
N1A0.0135 (6)0.0196 (6)0.0193 (6)0.0008 (5)−0.0005 (5)−0.0012 (5)
N2A0.0147 (6)0.0260 (7)0.0153 (6)−0.0054 (5)−0.0024 (5)0.0021 (5)
C1A0.0227 (8)0.0187 (7)0.0227 (7)−0.0042 (6)0.0001 (6)−0.0014 (6)
C2A0.0166 (7)0.0242 (8)0.0209 (7)−0.0050 (6)0.0015 (6)−0.0054 (6)
C3A0.0138 (7)0.0232 (7)0.0192 (7)−0.0020 (6)−0.0001 (6)−0.0026 (6)
C4A0.0145 (7)0.0186 (7)0.0168 (6)−0.0009 (5)0.0017 (5)−0.0019 (5)
C5A0.0143 (6)0.0188 (7)0.0157 (6)−0.0027 (6)0.0006 (5)−0.0015 (5)
C6A0.0187 (7)0.0205 (7)0.0169 (6)−0.0022 (6)0.0000 (6)0.0007 (6)
C7A0.0224 (8)0.0189 (7)0.0254 (7)−0.0007 (6)−0.0051 (7)0.0026 (6)
C8A0.0181 (7)0.0207 (7)0.0239 (7)0.0029 (6)−0.0019 (6)−0.0024 (6)
C9A0.0129 (6)0.0182 (6)0.0162 (6)−0.0016 (5)−0.0005 (5)0.0002 (5)
C10A0.0150 (7)0.0236 (7)0.0181 (6)−0.0032 (6)0.0010 (5)−0.0032 (6)
C11A0.0145 (7)0.0254 (8)0.0235 (7)−0.0012 (6)−0.0011 (6)−0.0069 (6)
C12A0.0127 (6)0.0223 (7)0.0159 (6)−0.0036 (6)−0.0013 (5)0.0013 (5)
C13A0.0150 (6)0.0243 (7)0.0128 (6)−0.0024 (6)0.0020 (5)0.0016 (5)
C14A0.0153 (6)0.0169 (6)0.0176 (6)−0.0017 (6)−0.0009 (5)−0.0014 (5)
C15A0.0143 (6)0.0174 (7)0.0180 (6)−0.0029 (5)−0.0007 (5)0.0002 (5)
C16A0.0186 (8)0.0366 (10)0.0220 (8)−0.0094 (7)−0.0027 (6)0.0058 (7)
C17A0.0228 (8)0.0416 (10)0.0233 (8)−0.0095 (8)−0.0072 (7)0.0087 (7)
C18A0.0166 (7)0.0294 (8)0.0287 (8)−0.0024 (7)−0.0061 (6)0.0012 (7)
C19A0.0149 (7)0.0277 (8)0.0248 (8)−0.0016 (6)0.0018 (6)−0.0008 (7)
C20A0.0165 (7)0.0195 (7)0.0196 (7)−0.0015 (6)0.0013 (6)−0.0005 (6)
C21A0.0227 (9)0.0336 (10)0.0440 (11)−0.0034 (8)−0.0113 (8)−0.0088 (9)
C22A0.0172 (7)0.0243 (8)0.0254 (8)0.0022 (6)−0.0036 (6)0.0025 (6)
O1B0.0162 (5)0.0241 (6)0.0207 (5)0.0038 (5)−0.0023 (4)0.0040 (4)
O2B0.0140 (5)0.0276 (6)0.0273 (6)−0.0045 (5)−0.0055 (5)0.0033 (5)
O3B0.0160 (5)0.0160 (5)0.0307 (6)0.0002 (4)−0.0041 (5)0.0065 (5)
O4B0.0198 (5)0.0349 (7)0.0176 (5)0.0002 (5)−0.0015 (5)0.0040 (5)
N1B0.0133 (6)0.0166 (6)0.0177 (6)0.0010 (5)−0.0027 (5)0.0017 (5)
N2B0.0138 (6)0.0281 (7)0.0162 (6)−0.0020 (5)−0.0032 (5)0.0013 (5)
C1B0.0144 (6)0.0181 (7)0.0177 (6)−0.0028 (5)−0.0005 (5)0.0007 (6)
C2B0.0121 (6)0.0238 (7)0.0162 (6)−0.0009 (6)−0.0009 (5)−0.0018 (6)
C3B0.0125 (6)0.0209 (7)0.0176 (7)0.0016 (6)−0.0013 (5)0.0001 (5)
C4B0.0140 (6)0.0164 (6)0.0155 (6)−0.0002 (5)−0.0004 (5)0.0007 (5)
C5B0.0126 (6)0.0178 (6)0.0146 (6)0.0001 (5)−0.0011 (5)−0.0002 (5)
C6B0.0147 (6)0.0169 (7)0.0144 (6)−0.0006 (5)−0.0003 (5)−0.0004 (5)
C7B0.0158 (7)0.0175 (7)0.0194 (7)−0.0010 (6)−0.0023 (5)0.0043 (5)
C8B0.0158 (6)0.0155 (6)0.0201 (7)−0.0001 (5)−0.0021 (5)0.0010 (6)
C9B0.0118 (6)0.0148 (6)0.0173 (6)0.0006 (5)−0.0017 (5)0.0018 (5)
C10B0.0150 (7)0.0227 (7)0.0216 (7)0.0006 (6)−0.0025 (6)−0.0044 (6)
C11B0.0150 (7)0.0269 (8)0.0245 (8)0.0022 (6)−0.0050 (6)−0.0047 (7)
C12B0.0117 (6)0.0214 (7)0.0172 (6)−0.0017 (5)−0.0028 (5)0.0022 (6)
C13B0.0135 (6)0.0211 (7)0.0136 (6)0.0000 (6)0.0005 (5)0.0020 (5)
C14B0.0133 (6)0.0196 (7)0.0202 (7)−0.0018 (6)−0.0034 (5)0.0028 (6)
C15B0.0138 (7)0.0227 (7)0.0209 (7)−0.0019 (6)−0.0037 (6)0.0020 (6)
C16B0.0178 (8)0.0448 (11)0.0266 (8)0.0049 (8)−0.0022 (7)−0.0105 (8)
C17B0.0152 (8)0.0567 (14)0.0413 (11)0.0071 (9)−0.0048 (8)−0.0138 (10)
C18B0.0195 (8)0.0418 (11)0.0379 (10)−0.0010 (8)−0.0124 (8)0.0021 (9)
C19B0.0238 (9)0.0661 (15)0.0243 (8)−0.0120 (10)−0.0075 (7)0.0066 (9)
C20B0.0173 (8)0.0568 (13)0.0207 (8)−0.0075 (8)−0.0019 (6)0.0036 (8)
C21B0.0150 (7)0.0342 (9)0.0278 (8)−0.0017 (7)−0.0059 (6)0.0069 (7)
C22B0.0237 (8)0.0167 (7)0.0334 (9)0.0044 (6)−0.0083 (7)0.0011 (6)
Geometric parameters (Å, º) top
O1A—C13A1.233 (2)O1B—C13B1.2358 (19)
O2A—C2A1.3708 (19)O2B—C2B1.3680 (19)
O2A—C21A1.426 (2)O2B—C21B1.436 (2)
O3A—C4A1.3706 (19)O3B—C4B1.3699 (19)
O3A—C22A1.4352 (19)O3B—C22B1.4251 (19)
O4A—C14A1.2342 (19)O4B—C14B1.235 (2)
N1A—C13A1.348 (2)N1B—C13B1.346 (2)
N1A—C8A1.464 (2)N1B—C8B1.460 (2)
N1A—C9A1.479 (2)N1B—C9B1.4825 (19)
N2A—C14A1.351 (2)N2B—C14B1.351 (2)
N2A—C12A1.4507 (19)N2B—C12B1.4441 (19)
N2A—H2AA0.8600N2B—H2BA0.8600
C1A—C2A1.386 (2)C1B—C6B1.389 (2)
C1A—C6A1.390 (2)C1B—C2B1.391 (2)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.391 (2)C2B—C3B1.393 (2)
C3A—C4A1.397 (2)C3B—C4B1.399 (2)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.399 (2)C4B—C5B1.401 (2)
C5A—C6A1.401 (2)C5B—C6B1.396 (2)
C5A—C9A1.515 (2)C5B—C9B1.513 (2)
C6A—C7A1.505 (2)C6B—C7B1.503 (2)
C7A—C8A1.511 (2)C7B—C8B1.524 (2)
C7A—H7AA0.9700C7B—H7BA0.9700
C7A—H7AB0.9700C7B—H7BB0.9700
C8A—H8AA0.9700C8B—H8BA0.9700
C8A—H8AB0.9700C8B—H8BB0.9700
C9A—C10A1.541 (2)C9B—C10B1.542 (2)
C9A—H9AA0.9800C9B—H9BA0.9800
C10A—C11A1.536 (2)C10B—C11B1.537 (2)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—C12A1.534 (2)C11B—C12B1.529 (2)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.530 (2)C12B—C13B1.530 (2)
C12A—H12A0.9800C12B—H12B0.9800
C14A—C15A1.508 (2)C14B—C15B1.499 (2)
C15A—C20A1.393 (2)C15B—C16B1.380 (2)
C15A—C16A1.397 (2)C15B—C20B1.400 (2)
C16A—C17A1.391 (2)C16B—C17B1.389 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.382 (3)C17B—C18B1.381 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.388 (2)C18B—C19B1.393 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.391 (2)C19B—C20B1.390 (2)
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9300C20B—H20B0.9300
C21A—H21A0.9600C21B—H21D0.9600
C21A—H21B0.9600C21B—H21G0.9600
C21A—H21C0.9600C21B—H21E0.9600
C22A—H22A0.9600C22B—H22G0.9600
C22A—H22B0.9600C22B—H22D0.9600
C22A—H22C0.9600C22B—H22E0.9600
C2A—O2A—C21A117.65 (15)C2B—O2B—C21B117.12 (13)
C4A—O3A—C22A116.49 (13)C4B—O3B—C22B117.29 (13)
C13A—N1A—C8A119.25 (14)C13B—N1B—C8B119.67 (13)
C13A—N1A—C9A119.79 (13)C13B—N1B—C9B119.13 (13)
C8A—N1A—C9A120.89 (13)C8B—N1B—C9B121.15 (12)
C14A—N2A—C12A121.39 (13)C14B—N2B—C12B121.00 (13)
C14A—N2A—H2AA119.3C14B—N2B—H2BA119.5
C12A—N2A—H2AA119.3C12B—N2B—H2BA119.5
C2A—C1A—C6A119.97 (15)C6B—C1B—C2B120.27 (15)
C2A—C1A—H1AA120.0C6B—C1B—H1BA119.9
C6A—C1A—H1AA120.0C2B—C1B—H1BA119.9
O2A—C2A—C1A115.69 (15)O2B—C2B—C1B115.77 (14)
O2A—C2A—C3A123.48 (16)O2B—C2B—C3B123.73 (14)
C1A—C2A—C3A120.82 (15)C1B—C2B—C3B120.50 (14)
C2A—C3A—C4A118.56 (16)C2B—C3B—C4B118.42 (14)
C2A—C3A—H3AA120.7C2B—C3B—H3BA120.8
C4A—C3A—H3AA120.7C4B—C3B—H3BA120.8
O3A—C4A—C3A122.21 (15)O3B—C4B—C3B122.73 (14)
O3A—C4A—C5A115.92 (14)O3B—C4B—C5B115.27 (13)
C3A—C4A—C5A121.86 (15)C3B—C4B—C5B122.00 (14)
C4A—C5A—C6A117.93 (15)C6B—C5B—C4B117.98 (14)
C4A—C5A—C9A119.45 (14)C6B—C5B—C9B122.57 (13)
C6A—C5A—C9A122.61 (15)C4B—C5B—C9B119.41 (14)
C1A—C6A—C5A120.83 (16)C1B—C6B—C5B120.82 (14)
C1A—C6A—C7A120.02 (15)C1B—C6B—C7B120.27 (14)
C5A—C6A—C7A119.09 (15)C5B—C6B—C7B118.88 (13)
C6A—C7A—C8A109.38 (13)C6B—C7B—C8B108.91 (12)
C6A—C7A—H7AA109.8C6B—C7B—H7BA109.9
C8A—C7A—H7AA109.8C8B—C7B—H7BA109.9
C6A—C7A—H7AB109.8C6B—C7B—H7BB109.9
C8A—C7A—H7AB109.8C8B—C7B—H7BB109.9
H7AA—C7A—H7AB108.2H7BA—C7B—H7BB108.3
N1A—C8A—C7A110.25 (14)N1B—C8B—C7B109.58 (13)
N1A—C8A—H8AA109.6N1B—C8B—H8BA109.8
C7A—C8A—H8AA109.6C7B—C8B—H8BA109.8
N1A—C8A—H8AB109.6N1B—C8B—H8BB109.8
C7A—C8A—H8AB109.6C7B—C8B—H8BB109.8
H8AA—C8A—H8AB108.1H8BA—C8B—H8BB108.2
N1A—C9A—C5A111.74 (13)N1B—C9B—C5B111.39 (12)
N1A—C9A—C10A107.69 (12)N1B—C9B—C10B108.66 (12)
C5A—C9A—C10A111.62 (13)C5B—C9B—C10B111.08 (12)
N1A—C9A—H9AA108.6N1B—C9B—H9BA108.5
C5A—C9A—H9AA108.6C5B—C9B—H9BA108.5
C10A—C9A—H9AA108.6C10B—C9B—H9BA108.5
C11A—C10A—C9A112.61 (13)C11B—C10B—C9B112.73 (13)
C11A—C10A—H10A109.1C11B—C10B—H10C109.0
C9A—C10A—H10A109.1C9B—C10B—H10C109.0
C11A—C10A—H10B109.1C11B—C10B—H10D109.0
C9A—C10A—H10B109.1C9B—C10B—H10D109.0
H10A—C10A—H10B107.8H10C—C10B—H10D107.8
C12A—C11A—C10A112.80 (13)C12B—C11B—C10B112.17 (13)
C12A—C11A—H11A109.0C12B—C11B—H11C109.2
C10A—C11A—H11A109.0C10B—C11B—H11C109.2
C12A—C11A—H11B109.0C12B—C11B—H11D109.2
C10A—C11A—H11B109.0C10B—C11B—H11D109.2
H11A—C11A—H11B107.8H11C—C11B—H11D107.9
N2A—C12A—C13A109.26 (13)N2B—C12B—C11B111.09 (13)
N2A—C12A—C11A112.25 (13)N2B—C12B—C13B110.63 (13)
C13A—C12A—C11A110.73 (13)C11B—C12B—C13B109.91 (13)
N2A—C12A—H12A108.2N2B—C12B—H12B108.4
C13A—C12A—H12A108.2C11B—C12B—H12B108.4
C11A—C12A—H12A108.2C13B—C12B—H12B108.4
O1A—C13A—N1A123.51 (15)O1B—C13B—N1B123.04 (15)
O1A—C13A—C12A121.57 (14)O1B—C13B—C12B122.22 (14)
N1A—C13A—C12A114.92 (14)N1B—C13B—C12B114.71 (13)
O4A—C14A—N2A122.02 (15)O4B—C14B—N2B121.87 (14)
O4A—C14A—C15A120.70 (14)O4B—C14B—C15B120.78 (15)
N2A—C14A—C15A117.27 (13)N2B—C14B—C15B117.31 (14)
C20A—C15A—C16A119.02 (15)C16B—C15B—C20B119.09 (16)
C20A—C15A—C14A117.31 (13)C16B—C15B—C14B117.62 (15)
C16A—C15A—C14A123.58 (15)C20B—C15B—C14B123.28 (16)
C17A—C16A—C15A120.18 (16)C15B—C16B—C17B120.98 (17)
C17A—C16A—H16A119.9C15B—C16B—H16B119.5
C15A—C16A—H16A119.9C17B—C16B—H16B119.5
C18A—C17A—C16A120.41 (16)C18B—C17B—C16B120.11 (19)
C18A—C17A—H17A119.8C18B—C17B—H17B119.9
C16A—C17A—H17A119.8C16B—C17B—H17B119.9
C17A—C18A—C19A119.85 (16)C17B—C18B—C19B119.47 (18)
C17A—C18A—H18A120.1C17B—C18B—H18B120.3
C19A—C18A—H18A120.1C19B—C18B—H18B120.3
C18A—C19A—C20A120.01 (16)C20B—C19B—C18B120.42 (18)
C18A—C19A—H19A120.0C20B—C19B—H19B119.8
C20A—C19A—H19A120.0C18B—C19B—H19B119.8
C19A—C20A—C15A120.53 (15)C19B—C20B—C15B119.90 (18)
C19A—C20A—H20A119.7C19B—C20B—H20B120.0
C15A—C20A—H20A119.7C15B—C20B—H20B120.0
O2A—C21A—H21A109.5O2B—C21B—H21D109.5
O2A—C21A—H21B109.5O2B—C21B—H21G109.5
H21A—C21A—H21B109.5H21D—C21B—H21G109.5
O2A—C21A—H21C109.5O2B—C21B—H21E109.5
H21A—C21A—H21C109.5H21D—C21B—H21E109.5
H21B—C21A—H21C109.5H21G—C21B—H21E109.5
O3A—C22A—H22A109.5O3B—C22B—H22G109.5
O3A—C22A—H22B109.5O3B—C22B—H22D109.5
H22A—C22A—H22B109.5H22G—C22B—H22D109.5
O3A—C22A—H22C109.5O3B—C22B—H22E109.5
H22A—C22A—H22C109.5H22G—C22B—H22E109.5
H22B—C22A—H22C109.5H22D—C22B—H22E109.5
C21A—O2A—C2A—C1A159.88 (17)C21B—O2B—C2B—C1B174.41 (15)
C21A—O2A—C2A—C3A−21.3 (2)C21B—O2B—C2B—C3B−6.3 (2)
C6A—C1A—C2A—O2A179.85 (15)C6B—C1B—C2B—O2B−179.61 (14)
C6A—C1A—C2A—C3A1.0 (3)C6B—C1B—C2B—C3B1.0 (2)
O2A—C2A—C3A—C4A−178.45 (15)O2B—C2B—C3B—C4B−179.22 (14)
C1A—C2A—C3A—C4A0.3 (2)C1B—C2B—C3B—C4B0.1 (2)
C22A—O3A—C4A—C3A−20.5 (2)C22B—O3B—C4B—C3B−16.2 (2)
C22A—O3A—C4A—C5A160.26 (14)C22B—O3B—C4B—C5B164.01 (14)
C2A—C3A—C4A—O3A178.87 (15)C2B—C3B—C4B—O3B179.13 (14)
C2A—C3A—C4A—C5A−1.9 (2)C2B—C3B—C4B—C5B−1.1 (2)
O3A—C4A—C5A—C6A−178.64 (14)O3B—C4B—C5B—C6B−179.22 (13)
C3A—C4A—C5A—C6A2.1 (2)C3B—C4B—C5B—C6B1.0 (2)
O3A—C4A—C5A—C9A0.1 (2)O3B—C4B—C5B—C9B−1.4 (2)
C3A—C4A—C5A—C9A−179.18 (14)C3B—C4B—C5B—C9B178.84 (14)
C2A—C1A—C6A—C5A−0.8 (3)C2B—C1B—C6B—C5B−1.2 (2)
C2A—C1A—C6A—C7A176.35 (16)C2B—C1B—C6B—C7B176.58 (14)
C4A—C5A—C6A—C1A−0.7 (2)C4B—C5B—C6B—C1B0.1 (2)
C9A—C5A—C6A—C1A−179.43 (15)C9B—C5B—C6B—C1B−177.62 (14)
C4A—C5A—C6A—C7A−177.87 (14)C4B—C5B—C6B—C7B−177.63 (13)
C9A—C5A—C6A—C7A3.4 (2)C9B—C5B—C6B—C7B4.6 (2)
C1A—C6A—C7A—C8A−143.01 (16)C1B—C6B—C7B—C8B−142.50 (14)
C5A—C6A—C7A—C8A34.2 (2)C5B—C6B—C7B—C8B35.28 (19)
C13A—N1A—C8A—C7A−136.11 (15)C13B—N1B—C8B—C7B−136.37 (14)
C9A—N1A—C8A—C7A46.98 (19)C9B—N1B—C8B—C7B46.03 (18)
C6A—C7A—C8A—N1A−57.11 (18)C6B—C7B—C8B—N1B−58.29 (16)
C13A—N1A—C9A—C5A173.50 (13)C13B—N1B—C9B—C5B175.51 (12)
C8A—N1A—C9A—C5A−9.60 (19)C8B—N1B—C9B—C5B−6.88 (19)
C13A—N1A—C9A—C10A50.58 (18)C13B—N1B—C9B—C10B52.84 (17)
C8A—N1A—C9A—C10A−132.52 (15)C8B—N1B—C9B—C10B−129.55 (14)
C4A—C5A—C9A—N1A164.37 (13)C6B—C5B—C9B—N1B−20.2 (2)
C6A—C5A—C9A—N1A−16.9 (2)C4B—C5B—C9B—N1B162.07 (13)
C4A—C5A—C9A—C10A−74.98 (18)C6B—C5B—C9B—C10B101.07 (17)
C6A—C5A—C9A—C10A103.70 (18)C4B—C5B—C9B—C10B−76.66 (17)
N1A—C9A—C10A—C11A−52.65 (17)N1B—C9B—C10B—C11B−47.00 (18)
C5A—C9A—C10A—C11A−175.65 (14)C5B—C9B—C10B—C11B−169.86 (14)
C9A—C10A—C11A—C12A7.5 (2)C9B—C10B—C11B—C12B−2.2 (2)
C14A—N2A—C12A—C13A−92.77 (17)C14B—N2B—C12B—C11B155.09 (16)
C14A—N2A—C12A—C11A143.99 (16)C14B—N2B—C12B—C13B−82.56 (18)
C10A—C11A—C12A—N2A164.68 (14)C10B—C11B—C12B—N2B172.47 (14)
C10A—C11A—C12A—C13A42.28 (18)C10B—C11B—C12B—C13B49.70 (18)
C8A—N1A—C13A—O1A4.1 (2)C8B—N1B—C13B—O1B0.6 (2)
C9A—N1A—C13A—O1A−178.95 (14)C9B—N1B—C13B—O1B178.26 (14)
C8A—N1A—C13A—C12A−176.20 (13)C8B—N1B—C13B—C12B178.49 (13)
C9A—N1A—C13A—C12A0.7 (2)C9B—N1B—C13B—C12B−3.87 (19)
N2A—C12A—C13A—O1A6.5 (2)N2B—C12B—C13B—O1B6.0 (2)
C11A—C12A—C13A—O1A130.60 (15)C11B—C12B—C13B—O1B129.01 (16)
N2A—C12A—C13A—N1A−173.23 (13)N2B—C12B—C13B—N1B−171.92 (12)
C11A—C12A—C13A—N1A−49.10 (17)C11B—C12B—C13B—N1B−48.88 (17)
C12A—N2A—C14A—O4A−17.9 (2)C12B—N2B—C14B—O4B−7.1 (3)
C12A—N2A—C14A—C15A160.86 (14)C12B—N2B—C14B—C15B175.32 (15)
O4A—C14A—C15A—C20A9.4 (2)O4B—C14B—C15B—C16B8.7 (3)
N2A—C14A—C15A—C20A−169.43 (14)N2B—C14B—C15B—C16B−173.72 (18)
O4A—C14A—C15A—C16A−174.28 (17)O4B—C14B—C15B—C20B−170.10 (19)
N2A—C14A—C15A—C16A6.9 (2)N2B—C14B—C15B—C20B7.5 (3)
C20A—C15A—C16A—C17A0.0 (3)C20B—C15B—C16B—C17B−1.3 (3)
C14A—C15A—C16A—C17A−176.24 (17)C14B—C15B—C16B—C17B179.9 (2)
C15A—C16A—C17A—C18A−0.3 (3)C15B—C16B—C17B—C18B0.3 (4)
C16A—C17A—C18A—C19A0.3 (3)C16B—C17B—C18B—C19B1.1 (4)
C17A—C18A—C19A—C20A0.0 (3)C17B—C18B—C19B—C20B−1.4 (4)
C18A—C19A—C20A—C15A−0.3 (3)C18B—C19B—C20B—C15B0.4 (4)
C16A—C15A—C20A—C19A0.2 (3)C16B—C15B—C20B—C19B1.0 (3)
C14A—C15A—C20A—C19A176.76 (15)C14B—C15B—C20B—C19B179.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1A–C6A and C15A–C20A benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O1Bi0.862.082.8994 (18)158
N2B—H2BA···O1Aii0.862.242.9807 (18)145
C1A—H1AA···O4Biii0.932.523.405 (2)160
C10A—H10B···O3A0.972.583.127 (2)115
C3B—H3BA···O4Aiv0.932.493.348 (2)153
C7B—H7BB···O4Av0.972.473.407 (2)163
C16A—H16A···O1Bi0.932.323.228 (2)165
C20B—H20B···O1Aii0.932.513.281 (2)141
C22A—H22A···O2Aiv0.962.523.266 (2)135
C22A—H22B···O4Bvi0.962.473.393 (2)160
C22B—H22D···O4Aiv0.962.583.414 (2)146
C11A—H11B···Cg2ii0.972.783.686 (2)156
C8B—H8BA···Cg1iv0.972.603.4864 (17)152
C18B—H18B···Cg1i0.932.813.607 (2)144
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) x, y+1, z; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, y, z; (vi) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC22H24N2O4
Mr380.43
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)12.6530 (3), 15.5256 (4), 19.7819 (5)
V (Å3)3886.06 (17)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.56 × 0.44 × 0.41
Data collection
DiffractometerBruker SMART APEX2 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.952, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections		110999, 6224, 5979
Rint0.044
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.04
No. of reflections6224
No. of parameters509
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.60, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1A–C6A and C15A–C20A benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O1Bi0.862.082.8994 (18)158
N2B—H2BA···O1Aii0.862.242.9807 (18)145
C1A—H1AA···O4Biii0.932.523.405 (2)160
C10A—H10B···O3A0.972.583.127 (2)115
C3B—H3BA···O4Aiv0.932.493.348 (2)153
C7B—H7BB···O4Av0.972.473.407 (2)163
C16A—H16A···O1Bi0.932.323.228 (2)165
C20B—H20B···O1Aii0.932.513.281 (2)141
C22A—H22A···O2Aiv0.962.523.266 (2)135
C22A—H22B···O4Bvi0.962.473.393 (2)160
C22B—H22D···O4Aiv0.962.583.414 (2)146
C11A—H11B···Cg2ii0.972.783.686 (2)156
C8B—H8BA···Cg1iv0.972.603.4864 (17)152
C18B—H18B···Cg1i0.932.813.607 (2)144
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) x, y+1, z; (iv) −x+1, y−1/2, −z+1/2; (v) x+1, y, z; (vi) −x+1, y+1/2, −z+1/2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

PK thanks the Thailand Research Fund (TRF) for financial support. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Pages o113-o114
https://doi.org/10.1107/S1600536810050737
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