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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 68| Part 10| October 2012| Pages o2967-o2968
https://doi.org/10.1107/S1600536812039268

Ethyl 2-[4-(morpholin-4-yl)phen­yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-1,3-benzimidazole-5-carboxyl­ate monohydrate

Yeong Keng Yoon,a Mohamed Ashraf Ali,a Tan Soo Choon,a Suhana Arshadb‡ and Ibrahim Abdul Razakb*§

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 29 August 2012; accepted 14 September 2012; online 22 September 2012)

The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxyl­ate mol­ecules and two water mol­ecules. In both main mol­ecules, the pyrrolidine rings are in an envelope conformation with a methyl­ene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one mol­ecule, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main mol­ecules and pairs of water mol­ecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.

Related literature

For the biological activity of benzimidazoles, see: Townsend & Revankar (1970[Townsend, L. B. & Revankar, G. R. (1970). Chem. Rev. 70, 389-438.]); Dubey & Sanyal (2010[Dubey, A. K. & Sanyal, P. K. (2010). Vet. Scan. 5, 63.]). For related structures, see: Yoon, Ali, Wei et al. (2011[Yoon, Y. K., Ali, M. A., Wei, A. C., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2405.]); Yoon et al. (2012[Yoon, Y. K., Ali, M. A., Wei, A. C., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o471-o472.]); Yoon, Ali, Choon et al. (2011[Yoon, Y. K., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3060.]). For ring conformations, 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.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For 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

  • C27H32N4O4·H2O

  • Mr = 494.58

  • Triclinic, [P \overline 1]

  • a = 12.2602 (3) Å

  • b = 13.7267 (4) Å

  • c = 15.3163 (4) Å

  • α = 99.357 (1)°

  • β = 93.700 (1)°

  • γ = 94.003 (1)°

  • V = 2529.56 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.67 × 0.40 × 0.11 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.991

  • 61724 measured reflections

  • 14611 independent reflections

  • 10995 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.152

  • S = 1.03

  • 14611 reflections

  • 667 parameters

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

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C17A—H17B⋯O3A 0.99 2.50 3.2624 (18) 133
O1WA—H1WA⋯O3Bi 0.88 (3) 2.00 (3) 2.8652 (18) 168 (2)
O1WA—H2WA⋯N1Bii 0.91 (3) 2.01 (3) 2.9142 (18) 172 (2)
O1WB—H1WB⋯N1A 0.87 (3) 2.05 (3) 2.9142 (19) 172 (2)
O1WB—H2WB⋯O3Aiii 0.83 (3) 1.99 (3) 2.8218 (18) 174 (2)
C15A—H15B⋯O2Biv 0.99 2.59 3.412 (2) 141
C15B—H15D⋯O2Aiv 0.99 2.50 3.227 (2) 130
C17A—H17A⋯O3Bi 0.99 2.44 3.4334 (18) 178
C17B—H17C⋯O3Ai 0.99 2.36 3.3274 (18) 166
C25A—H25A⋯O2Bv 0.99 2.37 3.309 (2) 159
C26A—H26B⋯O4Bvi 0.99 2.54 3.425 (2) 148
C13B—H13B⋯Cg1iii 0.95 2.87 3.5419 (15) 129
C21B—H21D⋯Cg2 0.99 2.96 3.8494 (18) 150
C24A—H24B⋯Cg3iii 0.99 2.79 3.7712 (19) 172
C24B—H24D⋯Cg4vii 0.99 2.67 3.6357 (17) 165
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x, y, z-1; (vi) -x+1, -y, -z-1; (vii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. 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/S1600536812039268/lh5526sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039268/lh5526Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039268/lh5526Isup3.cml

checkCIF report


Comment top

Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activities such as anti-cancer (Townsend & Revankar, 1970) and anthelmintics (Dubey & Sanyal, 2010). As part of our ongoing structural studies of benzimidazole derivatives (Yoon, Ali, Wei et al. 2011), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of two crystallographically independent (A and B) Ethyl 2-(4-morpholinophenyl)-1-(3-oxopyrolidin-1-yl) propyl)-1H-benzo [d]imidazole-5-carboxylate and two water molecules. In both molecules, the pyrrolidine rings (N3A/C20A–C23A & N3B/C20B–C23B) are in envelope conformations (Cremer & Pople, 1975) with puckering parameters, Q= 0.2575 (19) Å and φ= 69.4 (4)° in which C21A is the flap and Q= 0.2563 (17) Å and φ= 71.7 (4)° in which C21B is the flap. The morpholine rings, O4A/N4A/C24A–C27A [puckering paramaters; Q = 0.4341 (18) Å, Θ= 1.1 (3)° and φ= 256 (10)°] and O4B/N4B/C24B–C27B [puckering paramaters; Q = 0.5605 (16) Å, Θ= 176.18 (16)° and φ= 153 (3)°] adopt chair conformations. The benzimidazole rings (N1A/N2A/C1A–C7A and N1B/N2B/C1B–C7B) are essentially planar with maximum deviation of 0.008 (1) Å at atom N2A, C6B and C7B. In molecule A, the benzimidazole ring, N1A/N2A/C1A–C7A, forms a dihedral of 37.65 (6)° with the benzene (C8A–C13A) ring. The corresponding dihedral angle in molecule B is 45.44 (6)°. In molecule B, an intramolecular C17A—H17B···O3A hydrogen bond (Table 1) forms S(7) ring motif (Bernstein et al., 1995). The bond lengths and angles are within normal ranges and comparable to the related structures (Yoon, Ali, Wei et al., 2011; Yoon et al., 2012; Yoon, Ali, Choon et al., 2011).

In the crystal packing (Fig. 2), intermolecular O—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network. The intermolecular C13B—H13B···Cg1iii, C21B—H21D···Cg2, C24A—H24B···Cg3iii and C24B—H24D···Cg4vii (Table 1) interactions further stabilize the crystal structure (Cg1, Cg2, Cg3 and Cg4 are the centroids of N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively).

Related literature top

For the biological activity of benzimidazoles, see: Townsend & Revankar (1970); Dubey & Sanyal (2010). For related structures, see: Yoon, Ali, Wei et al. (2011); Yoon et al. (2012); Yoon, Ali, Choon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-morpholino benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 403K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate. The crystals were then removed and washed twice gently with cold ethyl acetate.

Refinement top

H atoms of the water molecules were located in a difference Fourier map and refined freely [O–H = 0.84 (3)–0.91 (3) Å]. All other H atoms were positioned geometrically [C–H = 0.95 and 0.99 Å] and refined using a riding model with Uiso(H) = 1.2 and 1.5 Ueq(C). A rotating group model was applied to the methyl groups. Two outliner reflections (0 0 1 and -9 - 2 12) were omitted in the final refinement.

Structure description top

Benzimidazoles belong to one of the well known and most extensively studied class of compounds due to their biological activities such as anti-cancer (Townsend & Revankar, 1970) and anthelmintics (Dubey & Sanyal, 2010). As part of our ongoing structural studies of benzimidazole derivatives (Yoon, Ali, Wei et al. 2011), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of two crystallographically independent (A and B) Ethyl 2-(4-morpholinophenyl)-1-(3-oxopyrolidin-1-yl) propyl)-1H-benzo [d]imidazole-5-carboxylate and two water molecules. In both molecules, the pyrrolidine rings (N3A/C20A–C23A & N3B/C20B–C23B) are in envelope conformations (Cremer & Pople, 1975) with puckering parameters, Q= 0.2575 (19) Å and φ= 69.4 (4)° in which C21A is the flap and Q= 0.2563 (17) Å and φ= 71.7 (4)° in which C21B is the flap. The morpholine rings, O4A/N4A/C24A–C27A [puckering paramaters; Q = 0.4341 (18) Å, Θ= 1.1 (3)° and φ= 256 (10)°] and O4B/N4B/C24B–C27B [puckering paramaters; Q = 0.5605 (16) Å, Θ= 176.18 (16)° and φ= 153 (3)°] adopt chair conformations. The benzimidazole rings (N1A/N2A/C1A–C7A and N1B/N2B/C1B–C7B) are essentially planar with maximum deviation of 0.008 (1) Å at atom N2A, C6B and C7B. In molecule A, the benzimidazole ring, N1A/N2A/C1A–C7A, forms a dihedral of 37.65 (6)° with the benzene (C8A–C13A) ring. The corresponding dihedral angle in molecule B is 45.44 (6)°. In molecule B, an intramolecular C17A—H17B···O3A hydrogen bond (Table 1) forms S(7) ring motif (Bernstein et al., 1995). The bond lengths and angles are within normal ranges and comparable to the related structures (Yoon, Ali, Wei et al., 2011; Yoon et al., 2012; Yoon, Ali, Choon et al., 2011).

In the crystal packing (Fig. 2), intermolecular O—H···O, C—H···N and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network. The intermolecular C13B—H13B···Cg1iii, C21B—H21D···Cg2, C24A—H24B···Cg3iii and C24B—H24D···Cg4vii (Table 1) interactions further stabilize the crystal structure (Cg1, Cg2, Cg3 and Cg4 are the centroids of N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively).

For the biological activity of benzimidazoles, see: Townsend & Revankar (1970); Dubey & Sanyal (2010). For related structures, see: Yoon, Ali, Wei et al. (2011); Yoon et al. (2012); Yoon, Ali, Choon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a hydrogen bond.
[Figure 2] Fig. 2. The crystal packing of the title compound. The H atoms not involved in the hydrogen bonds (dashed lines) have been omitted for clarity.
Ethyl 2-[4-(morpholin-4-yl)phenyl]-1-[3-(2-oxopyrrolidin-1-yl)propyl]- 1H-1,3-benzimidazole-5-carboxylate monohydrate top
Crystal data top
C27H32N4O4·H2OZ = 4
Mr = 494.58F(000) = 1056
Triclinic, P1Dx = 1.299 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.2602 (3) ÅCell parameters from 9908 reflections
b = 13.7267 (4) Åθ = 2.5–33.5°
c = 15.3163 (4) ŵ = 0.09 mm−1
α = 99.357 (1)°T = 100 K
β = 93.700 (1)°Plate, colourless
γ = 94.003 (1)°0.67 × 0.40 × 0.11 mm
V = 2529.56 (12) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14611 independent reflections
Radiation source: fine-focus sealed tube10995 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −17→17
Tmin = 0.942, Tmax = 0.991k = −19→19
61724 measured reflectionsl = −21→21
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0734P)2 + 1.0729P]
where P = (Fo2 + 2Fc2)/3
14611 reflections(Δ/σ)max = 0.001
667 parametersΔρmax = 0.58 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C27H32N4O4·H2Oγ = 94.003 (1)°
Mr = 494.58V = 2529.56 (12) Å3
Triclinic, P1Z = 4
a = 12.2602 (3) ÅMo Kα radiation
b = 13.7267 (4) ŵ = 0.09 mm−1
c = 15.3163 (4) ÅT = 100 K
α = 99.357 (1)°0.67 × 0.40 × 0.11 mm
β = 93.700 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14611 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		10995 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.991Rint = 0.042
61724 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.58 e Å−3
14611 reflectionsΔρmin = −0.37 e Å−3
667 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A0.66537 (9)0.88724 (8)0.48359 (7)0.0207 (2)
O2A0.80726 (9)0.79642 (8)0.44866 (7)0.0229 (2)
O3A0.25226 (9)0.68922 (8)−0.13551 (8)0.0235 (2)
O4A0.64255 (10)0.32281 (11)−0.46338 (9)0.0396 (4)
N1A0.68276 (10)0.65123 (9)0.11445 (8)0.0147 (2)
N2A0.52634 (9)0.71947 (9)0.08170 (8)0.0150 (2)
N3A0.38761 (10)0.80132 (9)−0.16261 (8)0.0184 (2)
N4A0.63208 (11)0.45033 (11)−0.29891 (8)0.0240 (3)
C1A0.65487 (11)0.71291 (10)0.18925 (9)0.0138 (3)
C2A0.70794 (11)0.73504 (10)0.27435 (9)0.0152 (3)
H2AA0.77330.70580.28870.018*
C3A0.66221 (11)0.80115 (10)0.33738 (9)0.0157 (3)
C4A0.56478 (12)0.84465 (11)0.31643 (10)0.0178 (3)
H4AA0.53550.88960.36110.021*
C5A0.51084 (12)0.82345 (11)0.23243 (10)0.0182 (3)
H5AA0.44550.85280.21820.022*
C6A0.55780 (11)0.75645 (10)0.16971 (9)0.0152 (3)
C7A0.60465 (11)0.65698 (10)0.05185 (9)0.0142 (3)
C8A0.60534 (11)0.60341 (10)−0.03932 (9)0.0141 (3)
C9A0.51195 (12)0.55865 (10)−0.09139 (9)0.0165 (3)
H9AA0.44210.5637−0.06830.020*
C10A0.51939 (12)0.50689 (11)−0.17616 (9)0.0172 (3)
H10A0.45460.4772−0.21030.021*
C11A0.62128 (12)0.49775 (11)−0.21216 (9)0.0161 (3)
C12A0.71504 (12)0.54133 (11)−0.15894 (9)0.0173 (3)
H12A0.78520.5356−0.18140.021*
C13A0.70707 (11)0.59237 (10)−0.07463 (9)0.0163 (3)
H13A0.77190.6206−0.03980.020*
C14A0.72009 (12)0.82628 (11)0.42737 (9)0.0169 (3)
C15A0.71598 (14)0.91412 (12)0.57342 (10)0.0256 (3)
H15A0.78530.95590.57410.031*
H15B0.73230.85400.59820.031*
C16A0.63542 (16)0.97026 (15)0.62659 (12)0.0353 (4)
H16A0.66390.98590.68900.053*
H16B0.56550.92980.62180.053*
H16C0.62401.03180.60390.053*
C17A0.43840 (11)0.75615 (11)0.02944 (9)0.0160 (3)
H17A0.37890.77480.06800.019*
H17B0.40770.7024−0.01880.019*
C18A0.47845 (12)0.84531 (11)−0.01077 (10)0.0187 (3)
H18A0.54680.8313−0.03980.022*
H18B0.49520.90340.03690.022*
C19A0.39221 (13)0.86937 (11)−0.07883 (10)0.0204 (3)
H19A0.31940.8663−0.05450.025*
H19B0.40930.9378−0.08960.025*
C20A0.45280 (15)0.82253 (13)−0.23446 (11)0.0293 (4)
H20A0.53030.8422−0.21270.035*
H20B0.42320.8759−0.26300.035*
C21A0.44200 (16)0.72360 (14)−0.29895 (12)0.0328 (4)
H21A0.43930.7345−0.36130.039*
H21B0.50400.6835−0.28800.039*
C22A0.33378 (14)0.67318 (13)−0.27850 (11)0.0270 (3)
H22A0.27270.6857−0.31960.032*
H22B0.33810.6008−0.28330.032*
C23A0.31818 (12)0.71960 (11)−0.18452 (10)0.0185 (3)
C24A0.53510 (13)0.41985 (14)−0.35701 (11)0.0285 (4)
H24A0.48810.4759−0.35470.034*
H24B0.49350.3650−0.33570.034*
C25A0.55943 (15)0.38658 (17)−0.45059 (11)0.0380 (5)
H25A0.49140.3532−0.48380.046*
H25B0.57930.4460−0.47700.046*
C26A0.73703 (15)0.35354 (15)−0.40709 (11)0.0340 (4)
H26A0.77600.4099−0.42810.041*
H26B0.78580.2987−0.41200.041*
C27A0.71833 (14)0.38407 (13)−0.31218 (11)0.0283 (4)
H27A0.69920.3242−0.28620.034*
H27B0.78720.4172−0.28020.034*
O1B0.17128 (9)0.40808 (8)0.45880 (7)0.0202 (2)
O2B0.32510 (9)0.33404 (8)0.42527 (7)0.0232 (2)
O3B−0.23642 (9)0.17337 (8)−0.16601 (8)0.0231 (2)
O4B0.12139 (10)−0.16714 (9)−0.48934 (7)0.0254 (2)
N1B0.20016 (10)0.15817 (9)0.09803 (8)0.0146 (2)
N2B0.04049 (9)0.21890 (9)0.06163 (8)0.0143 (2)
N3B−0.09212 (10)0.28326 (9)−0.18049 (8)0.0173 (2)
N4B0.13616 (10)−0.08559 (9)−0.30449 (8)0.0177 (2)
C1B0.17154 (11)0.22424 (10)0.16978 (9)0.0134 (3)
C2B0.22552 (11)0.25486 (10)0.25383 (9)0.0151 (3)
H2BA0.29300.22980.26980.018*
C3B0.17737 (11)0.32329 (10)0.31350 (9)0.0157 (3)
C4B0.07777 (12)0.36160 (11)0.28975 (9)0.0175 (3)
H4BA0.04730.40860.33200.021*
C5B0.02341 (12)0.33243 (11)0.20668 (9)0.0176 (3)
H5BA−0.04340.35840.19050.021*
C6B0.07180 (11)0.26286 (10)0.14780 (9)0.0145 (3)
C7B0.12087 (11)0.15719 (10)0.03483 (9)0.0138 (3)
C8B0.11987 (11)0.09680 (10)−0.05387 (9)0.0141 (3)
C9B0.02794 (12)0.03843 (10)−0.09653 (9)0.0156 (3)
H9BA−0.03930.0395−0.06900.019*
C10B0.03271 (12)−0.02111 (11)−0.17829 (9)0.0166 (3)
H10B−0.0311−0.0607−0.20510.020*
C11B0.12970 (12)−0.02411 (10)−0.22224 (9)0.0153 (3)
C12B0.22229 (12)0.03535 (11)−0.17892 (9)0.0175 (3)
H12B0.28940.0354−0.20670.021*
C13B0.21727 (11)0.09352 (10)−0.09678 (9)0.0163 (3)
H13B0.28130.1320−0.06890.020*
C14B0.23436 (12)0.35468 (11)0.40338 (9)0.0172 (3)
C15B0.21555 (13)0.43897 (12)0.55009 (10)0.0223 (3)
H15C0.27020.49650.55470.027*
H15D0.25160.38430.57190.027*
C16B0.12101 (16)0.46633 (18)0.60303 (12)0.0411 (5)
H16D0.14710.48700.66560.062*
H16E0.06720.40900.59720.062*
H16F0.08670.52100.58110.062*
C17B−0.05096 (11)0.24722 (11)0.00739 (9)0.0158 (3)
H17C−0.11560.25380.04280.019*
H17D−0.07060.1942−0.04440.019*
C18B−0.02321 (13)0.34433 (11)−0.02516 (10)0.0195 (3)
H18C0.05220.3455−0.04480.023*
H18D−0.02590.40030.02410.023*
C19B−0.10395 (13)0.35643 (11)−0.10218 (10)0.0206 (3)
H19C−0.17980.3491−0.08420.025*
H19D−0.09100.4238−0.11670.025*
C20B−0.00713 (13)0.29695 (12)−0.24108 (11)0.0254 (3)
H20C0.06480.3189−0.20800.030*
H20D−0.02620.3462−0.27900.030*
C21B−0.00526 (13)0.19367 (13)−0.29671 (11)0.0256 (3)
H21C0.00880.1982−0.35890.031*
H21D0.05160.1561−0.27160.031*
C22B−0.11994 (13)0.14519 (12)−0.29112 (10)0.0217 (3)
H22C−0.16930.1531−0.34280.026*
H22D−0.11750.0737−0.28890.026*
C23B−0.15789 (11)0.19944 (11)−0.20610 (9)0.0171 (3)
C24B0.03344 (13)−0.13261 (12)−0.35087 (10)0.0226 (3)
H24C−0.0104−0.0815−0.37120.027*
H24D−0.0095−0.1652−0.30950.027*
C25B0.05476 (14)−0.20895 (12)−0.43018 (11)0.0254 (3)
H25C0.0915−0.2637−0.40910.030*
H25D−0.0161−0.2369−0.46220.030*
C26B0.22365 (14)−0.12744 (12)−0.44363 (10)0.0247 (3)
H26C0.2709−0.0998−0.48520.030*
H26D0.2613−0.1810−0.42120.030*
C27B0.20697 (14)−0.04717 (12)−0.36697 (10)0.0236 (3)
H27C0.2789−0.0211−0.33580.028*
H27D0.17310.0081−0.38980.028*
O1WA0.34451 (10)1.00467 (10)0.12704 (10)0.0318 (3)
O1WB0.83897 (11)0.50664 (10)0.14244 (12)0.0425 (4)
H1WA0.303 (2)0.955 (2)0.1401 (16)0.052 (7)*
H2WA0.295 (2)1.048 (2)0.1147 (17)0.061 (8)*
H1WB0.790 (2)0.5461 (19)0.1295 (16)0.052 (7)*
H2WB0.808 (2)0.450 (2)0.1384 (17)0.054 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0249 (5)0.0226 (5)0.0130 (5)0.0054 (4)0.0001 (4)−0.0023 (4)
O2A0.0218 (5)0.0278 (6)0.0175 (5)0.0051 (4)−0.0023 (4)−0.0006 (4)
O3A0.0185 (5)0.0212 (5)0.0304 (6)−0.0006 (4)0.0018 (4)0.0040 (5)
O4A0.0298 (7)0.0514 (8)0.0284 (7)0.0123 (6)−0.0044 (5)−0.0222 (6)
N1A0.0156 (5)0.0144 (5)0.0133 (5)0.0020 (4)0.0000 (4)0.0005 (4)
N2A0.0155 (5)0.0162 (5)0.0127 (5)0.0034 (4)−0.0012 (4)0.0005 (4)
N3A0.0197 (6)0.0190 (6)0.0154 (6)−0.0020 (5)−0.0026 (5)0.0025 (5)
N4A0.0200 (6)0.0367 (8)0.0131 (6)0.0121 (6)−0.0037 (5)−0.0044 (5)
C1A0.0136 (6)0.0132 (6)0.0140 (6)0.0018 (5)0.0004 (5)0.0006 (5)
C2A0.0134 (6)0.0169 (6)0.0151 (7)0.0018 (5)−0.0004 (5)0.0021 (5)
C3A0.0157 (6)0.0166 (6)0.0136 (6)−0.0002 (5)0.0000 (5)0.0004 (5)
C4A0.0180 (7)0.0186 (7)0.0160 (7)0.0039 (5)0.0018 (5)−0.0010 (5)
C5A0.0154 (6)0.0200 (7)0.0184 (7)0.0056 (5)−0.0007 (5)0.0001 (5)
C6A0.0142 (6)0.0153 (6)0.0156 (7)0.0010 (5)−0.0004 (5)0.0018 (5)
C7A0.0145 (6)0.0124 (6)0.0153 (6)0.0006 (5)−0.0001 (5)0.0017 (5)
C8A0.0166 (6)0.0124 (6)0.0131 (6)0.0019 (5)0.0000 (5)0.0020 (5)
C9A0.0158 (6)0.0184 (7)0.0150 (7)0.0002 (5)0.0010 (5)0.0027 (5)
C10A0.0163 (6)0.0196 (7)0.0147 (7)0.0000 (5)−0.0019 (5)0.0011 (5)
C11A0.0184 (6)0.0185 (7)0.0119 (6)0.0048 (5)−0.0003 (5)0.0034 (5)
C12A0.0152 (6)0.0213 (7)0.0159 (7)0.0040 (5)0.0018 (5)0.0035 (5)
C13A0.0141 (6)0.0177 (6)0.0169 (7)0.0023 (5)−0.0006 (5)0.0023 (5)
C14A0.0184 (6)0.0167 (6)0.0146 (7)0.0002 (5)0.0016 (5)0.0005 (5)
C15A0.0358 (9)0.0258 (8)0.0131 (7)0.0072 (7)−0.0028 (6)−0.0033 (6)
C16A0.0399 (10)0.0419 (11)0.0213 (8)0.0027 (8)0.0081 (7)−0.0047 (7)
C17A0.0135 (6)0.0189 (7)0.0152 (7)0.0038 (5)−0.0027 (5)0.0024 (5)
C18A0.0201 (7)0.0163 (6)0.0181 (7)−0.0003 (5)−0.0049 (5)0.0013 (5)
C19A0.0254 (7)0.0141 (6)0.0203 (7)0.0020 (6)−0.0060 (6)0.0012 (5)
C20A0.0312 (9)0.0318 (9)0.0245 (8)−0.0057 (7)0.0041 (7)0.0061 (7)
C21A0.0381 (10)0.0381 (10)0.0214 (8)0.0013 (8)0.0082 (7)0.0010 (7)
C22A0.0326 (9)0.0273 (8)0.0178 (7)−0.0010 (7)−0.0050 (6)−0.0015 (6)
C23A0.0162 (6)0.0180 (7)0.0204 (7)0.0008 (5)−0.0052 (5)0.0036 (5)
C24A0.0185 (7)0.0396 (10)0.0218 (8)0.0042 (7)−0.0040 (6)−0.0094 (7)
C25A0.0316 (9)0.0608 (13)0.0186 (8)0.0215 (9)−0.0048 (7)−0.0074 (8)
C26A0.0340 (9)0.0451 (11)0.0210 (8)0.0200 (8)−0.0024 (7)−0.0054 (7)
C27A0.0281 (8)0.0307 (9)0.0233 (8)0.0136 (7)−0.0038 (6)−0.0065 (7)
O1B0.0226 (5)0.0223 (5)0.0136 (5)0.0063 (4)−0.0013 (4)−0.0044 (4)
O2B0.0198 (5)0.0301 (6)0.0170 (5)0.0051 (4)−0.0046 (4)−0.0032 (4)
O3B0.0177 (5)0.0255 (6)0.0272 (6)−0.0001 (4)0.0021 (4)0.0081 (5)
O4B0.0312 (6)0.0290 (6)0.0141 (5)0.0029 (5)0.0024 (4)−0.0023 (4)
N1B0.0174 (5)0.0146 (5)0.0112 (5)0.0029 (4)−0.0010 (4)−0.0001 (4)
N2B0.0140 (5)0.0163 (5)0.0117 (5)0.0021 (4)−0.0019 (4)−0.0001 (4)
N3B0.0165 (6)0.0202 (6)0.0149 (6)0.0002 (5)−0.0010 (4)0.0037 (5)
N4B0.0205 (6)0.0201 (6)0.0107 (5)−0.0014 (5)0.0011 (4)−0.0017 (4)
C1B0.0144 (6)0.0131 (6)0.0117 (6)0.0016 (5)−0.0003 (5)−0.0003 (5)
C2B0.0148 (6)0.0165 (6)0.0131 (6)0.0027 (5)−0.0016 (5)0.0007 (5)
C3B0.0158 (6)0.0174 (6)0.0128 (6)0.0018 (5)−0.0008 (5)−0.0001 (5)
C4B0.0167 (6)0.0199 (7)0.0147 (7)0.0051 (5)0.0008 (5)−0.0018 (5)
C5B0.0152 (6)0.0210 (7)0.0160 (7)0.0055 (5)−0.0004 (5)0.0003 (5)
C6B0.0143 (6)0.0160 (6)0.0124 (6)0.0010 (5)−0.0018 (5)0.0008 (5)
C7B0.0153 (6)0.0122 (6)0.0133 (6)0.0001 (5)−0.0006 (5)0.0014 (5)
C8B0.0172 (6)0.0134 (6)0.0109 (6)0.0015 (5)−0.0011 (5)0.0009 (5)
C9B0.0178 (6)0.0168 (6)0.0119 (6)−0.0010 (5)0.0016 (5)0.0024 (5)
C10B0.0184 (6)0.0172 (6)0.0128 (6)−0.0026 (5)−0.0009 (5)0.0009 (5)
C11B0.0206 (7)0.0153 (6)0.0096 (6)0.0016 (5)−0.0013 (5)0.0015 (5)
C12B0.0158 (6)0.0211 (7)0.0148 (7)0.0018 (5)0.0008 (5)0.0008 (5)
C13B0.0153 (6)0.0170 (6)0.0155 (7)0.0002 (5)−0.0014 (5)0.0008 (5)
C14B0.0189 (7)0.0176 (6)0.0136 (6)0.0017 (5)0.0001 (5)−0.0017 (5)
C15B0.0289 (8)0.0231 (7)0.0121 (7)0.0029 (6)−0.0027 (6)−0.0045 (5)
C16B0.0360 (10)0.0642 (14)0.0193 (9)0.0046 (9)0.0058 (7)−0.0061 (8)
C17B0.0132 (6)0.0197 (7)0.0142 (6)0.0026 (5)−0.0032 (5)0.0031 (5)
C18B0.0235 (7)0.0165 (7)0.0173 (7)0.0023 (5)−0.0059 (6)0.0014 (5)
C19B0.0247 (7)0.0190 (7)0.0178 (7)0.0058 (6)−0.0039 (6)0.0025 (5)
C20B0.0234 (8)0.0283 (8)0.0242 (8)−0.0039 (6)0.0050 (6)0.0051 (6)
C21B0.0246 (8)0.0320 (9)0.0200 (8)0.0021 (7)0.0062 (6)0.0021 (6)
C22B0.0247 (7)0.0249 (8)0.0147 (7)0.0007 (6)−0.0020 (6)0.0026 (6)
C23B0.0148 (6)0.0209 (7)0.0160 (7)0.0016 (5)−0.0042 (5)0.0062 (5)
C24B0.0218 (7)0.0264 (8)0.0164 (7)−0.0013 (6)−0.0006 (6)−0.0039 (6)
C25B0.0272 (8)0.0260 (8)0.0196 (8)−0.0015 (6)0.0000 (6)−0.0044 (6)
C26B0.0288 (8)0.0247 (8)0.0188 (7)0.0007 (6)0.0060 (6)−0.0023 (6)
C27B0.0296 (8)0.0220 (7)0.0176 (7)−0.0023 (6)0.0070 (6)−0.0012 (6)
O1WA0.0230 (6)0.0226 (6)0.0512 (8)0.0041 (5)−0.0005 (6)0.0104 (6)
O1WB0.0237 (6)0.0195 (6)0.0827 (12)0.0014 (5)−0.0133 (7)0.0104 (7)
Geometric parameters (Å, º) top
O1A—C14A1.3455 (17)O2B—C14B1.2070 (17)
O1A—C15A1.4515 (18)O3B—C23B1.2377 (18)
O2A—C14A1.2149 (18)O4B—C25B1.420 (2)
O3A—C23A1.2344 (19)O4B—C26B1.4235 (19)
O4A—C25A1.392 (2)N1B—C7B1.3247 (17)
O4A—C26A1.396 (2)N1B—C1B1.3869 (17)
N1A—C7A1.3264 (17)N2B—C6B1.3773 (17)
N1A—C1A1.3864 (17)N2B—C7B1.3830 (18)
N2A—C6A1.3808 (17)N2B—C17B1.4642 (17)
N2A—C7A1.3824 (17)N3B—C23B1.3456 (18)
N2A—C17A1.4669 (17)N3B—C19B1.4558 (19)
N3A—C23A1.3427 (18)N3B—C20B1.462 (2)
N3A—C19A1.4546 (19)N4B—C11B1.4080 (17)
N3A—C20A1.456 (2)N4B—C24B1.4591 (18)
N4A—C11A1.4001 (18)N4B—C27B1.468 (2)
N4A—C24A1.4330 (19)C1B—C2B1.3953 (18)
N4A—C27A1.445 (2)C1B—C6B1.4089 (18)
C1A—C2A1.3959 (18)C2B—C3B1.3906 (19)
C1A—C6A1.4053 (18)C2B—H2BA0.9500
C2A—C3A1.3877 (19)C3B—C4B1.4124 (19)
C2A—H2AA0.9500C3B—C14B1.4865 (19)
C3A—C4A1.4138 (19)C4B—C5B1.3824 (19)
C3A—C14A1.4857 (19)C4B—H4BA0.9500
C4A—C5A1.3852 (19)C5B—C6B1.3947 (19)
C4A—H4AA0.9500C5B—H5BA0.9500
C5A—C6A1.3993 (19)C7B—C8B1.4707 (18)
C5A—H5AA0.9500C8B—C9B1.3957 (18)
C7A—C8A1.4694 (19)C8B—C13B1.400 (2)
C8A—C9A1.3961 (18)C9B—C10B1.3867 (19)
C8A—C13A1.3992 (19)C9B—H9BA0.9500
C9A—C10A1.387 (2)C10B—C11B1.404 (2)
C9A—H9AA0.9500C10B—H10B0.9500
C10A—C11A1.403 (2)C11B—C12B1.4115 (19)
C10A—H10A0.9500C12B—C13B1.3835 (19)
C11A—C12A1.4029 (19)C12B—H12B0.9500
C12A—C13A1.378 (2)C13B—H13B0.9500
C12A—H12A0.9500C15B—C16B1.492 (2)
C13A—H13A0.9500C15B—H15C0.9900
C15A—C16A1.496 (2)C15B—H15D0.9900
C15A—H15A0.9900C16B—H16D0.9800
C15A—H15B0.9900C16B—H16E0.9800
C16A—H16A0.9800C16B—H16F0.9800
C16A—H16B0.9800C17B—C18B1.522 (2)
C16A—H16C0.9800C17B—H17C0.9900
C17A—C18A1.523 (2)C17B—H17D0.9900
C17A—H17A0.9900C18B—C19B1.5281 (19)
C17A—H17B0.9900C18B—H18C0.9900
C18A—C19A1.5271 (19)C18B—H18D0.9900
C18A—H18A0.9900C19B—H19C0.9900
C18A—H18B0.9900C19B—H19D0.9900
C19A—H19A0.9900C20B—C21B1.533 (2)
C19A—H19B0.9900C20B—H20C0.9900
C20A—C21A1.536 (2)C20B—H20D0.9900
C20A—H20A0.9900C21B—C22B1.527 (2)
C20A—H20B0.9900C21B—H21C0.9900
C21A—C22A1.528 (3)C21B—H21D0.9900
C21A—H21A0.9900C22B—C23B1.509 (2)
C21A—H21B0.9900C22B—H22C0.9900
C22A—C23A1.506 (2)C22B—H22D0.9900
C22A—H22A0.9900C24B—C25B1.519 (2)
C22A—H22B0.9900C24B—H24C0.9900
C24A—C25A1.488 (2)C24B—H24D0.9900
C24A—H24A0.9900C25B—H25C0.9900
C24A—H24B0.9900C25B—H25D0.9900
C25A—H25A0.9900C26B—C27B1.509 (2)
C25A—H25B0.9900C26B—H26C0.9900
C26A—C27A1.483 (2)C26B—H26D0.9900
C26A—H26A0.9900C27B—H27C0.9900
C26A—H26B0.9900C27B—H27D0.9900
C27A—H27A0.9900O1WA—H1WA0.88 (3)
C27A—H27B0.9900O1WA—H2WA0.91 (3)
O1B—C14B1.3482 (17)O1WB—H1WB0.87 (3)
O1B—C15B1.4514 (17)O1WB—H2WB0.84 (3)
C14A—O1A—C15A115.63 (12)C25B—O4B—C26B109.43 (12)
C25A—O4A—C26A113.58 (13)C7B—N1B—C1B105.19 (11)
C7A—N1A—C1A105.09 (11)C6B—N2B—C7B106.63 (11)
C6A—N2A—C7A106.39 (11)C6B—N2B—C17B124.46 (11)
C6A—N2A—C17A124.43 (11)C7B—N2B—C17B128.17 (11)
C7A—N2A—C17A128.26 (12)C23B—N3B—C19B124.77 (13)
C23A—N3A—C19A124.63 (13)C23B—N3B—C20B113.41 (12)
C23A—N3A—C20A113.69 (13)C19B—N3B—C20B121.79 (12)
C19A—N3A—C20A121.42 (13)C11B—N4B—C24B117.25 (12)
C11A—N4A—C24A118.85 (13)C11B—N4B—C27B116.73 (12)
C11A—N4A—C27A117.46 (12)C24B—N4B—C27B110.38 (12)
C24A—N4A—C27A113.95 (13)N1B—C1B—C2B130.21 (12)
N1A—C1A—C2A129.91 (12)N1B—C1B—C6B109.88 (11)
N1A—C1A—C6A109.98 (12)C2B—C1B—C6B119.91 (12)
C2A—C1A—C6A120.11 (12)C3B—C2B—C1B117.82 (12)
C3A—C2A—C1A117.90 (12)C3B—C2B—H2BA121.1
C3A—C2A—H2AA121.0C1B—C2B—H2BA121.1
C1A—C2A—H2AA121.0C2B—C3B—C4B121.27 (12)
C2A—C3A—C4A121.23 (13)C2B—C3B—C14B117.65 (12)
C2A—C3A—C14A117.83 (12)C4B—C3B—C14B121.07 (12)
C4A—C3A—C14A120.93 (12)C5B—C4B—C3B121.69 (13)
C5A—C4A—C3A121.70 (13)C5B—C4B—H4BA119.2
C5A—C4A—H4AA119.1C3B—C4B—H4BA119.2
C3A—C4A—H4AA119.1C4B—C5B—C6B116.50 (13)
C4A—C5A—C6A116.38 (13)C4B—C5B—H5BA121.8
C4A—C5A—H5AA121.8C6B—C5B—H5BA121.8
C6A—C5A—H5AA121.8N2B—C6B—C5B131.51 (13)
N2A—C6A—C5A131.51 (13)N2B—C6B—C1B105.69 (12)
N2A—C6A—C1A105.81 (12)C5B—C6B—C1B122.80 (12)
C5A—C6A—C1A122.68 (13)N1B—C7B—N2B112.61 (12)
N1A—C7A—N2A112.72 (12)N1B—C7B—C8B123.05 (12)
N1A—C7A—C8A122.28 (12)N2B—C7B—C8B124.34 (12)
N2A—C7A—C8A124.98 (12)C9B—C8B—C13B117.60 (12)
C9A—C8A—C13A117.83 (12)C9B—C8B—C7B123.58 (13)
C9A—C8A—C7A124.42 (13)C13B—C8B—C7B118.75 (12)
C13A—C8A—C7A117.68 (12)C10B—C9B—C8B121.37 (13)
C10A—C9A—C8A121.15 (13)C10B—C9B—H9BA119.3
C10A—C9A—H9AA119.4C8B—C9B—H9BA119.3
C8A—C9A—H9AA119.4C9B—C10B—C11B121.43 (13)
C9A—C10A—C11A120.90 (13)C9B—C10B—H10B119.3
C9A—C10A—H10A119.5C11B—C10B—H10B119.3
C11A—C10A—H10A119.5C10B—C11B—N4B121.98 (12)
N4A—C11A—C12A119.47 (13)C10B—C11B—C12B116.94 (12)
N4A—C11A—C10A122.80 (13)N4B—C11B—C12B121.06 (13)
C12A—C11A—C10A117.70 (13)C13B—C12B—C11B121.28 (13)
C13A—C12A—C11A121.08 (13)C13B—C12B—H12B119.4
C13A—C12A—H12A119.5C11B—C12B—H12B119.4
C11A—C12A—H12A119.5C12B—C13B—C8B121.37 (13)
C12A—C13A—C8A121.31 (13)C12B—C13B—H13B119.3
C12A—C13A—H13A119.3C8B—C13B—H13B119.3
C8A—C13A—H13A119.3O2B—C14B—O1B123.61 (13)
O2A—C14A—O1A123.10 (13)O2B—C14B—C3B124.76 (13)
O2A—C14A—C3A124.59 (13)O1B—C14B—C3B111.62 (12)
O1A—C14A—C3A112.30 (12)O1B—C15B—C16B106.61 (13)
O1A—C15A—C16A106.53 (14)O1B—C15B—H15C110.4
O1A—C15A—H15A110.4C16B—C15B—H15C110.4
C16A—C15A—H15A110.4O1B—C15B—H15D110.4
O1A—C15A—H15B110.4C16B—C15B—H15D110.4
C16A—C15A—H15B110.4H15C—C15B—H15D108.6
H15A—C15A—H15B108.6C15B—C16B—H16D109.5
C15A—C16A—H16A109.5C15B—C16B—H16E109.5
C15A—C16A—H16B109.5H16D—C16B—H16E109.5
H16A—C16A—H16B109.5C15B—C16B—H16F109.5
C15A—C16A—H16C109.5H16D—C16B—H16F109.5
H16A—C16A—H16C109.5H16E—C16B—H16F109.5
H16B—C16A—H16C109.5N2B—C17B—C18B112.14 (11)
N2A—C17A—C18A112.28 (11)N2B—C17B—H17C109.2
N2A—C17A—H17A109.1C18B—C17B—H17C109.2
C18A—C17A—H17A109.1N2B—C17B—H17D109.2
N2A—C17A—H17B109.1C18B—C17B—H17D109.2
C18A—C17A—H17B109.1H17C—C17B—H17D107.9
H17A—C17A—H17B107.9C17B—C18B—C19B110.76 (12)
C17A—C18A—C19A111.11 (12)C17B—C18B—H18C109.5
C17A—C18A—H18A109.4C19B—C18B—H18C109.5
C19A—C18A—H18A109.4C17B—C18B—H18D109.5
C17A—C18A—H18B109.4C19B—C18B—H18D109.5
C19A—C18A—H18B109.4H18C—C18B—H18D108.1
H18A—C18A—H18B108.0N3B—C19B—C18B111.28 (12)
N3A—C19A—C18A112.24 (12)N3B—C19B—H19C109.4
N3A—C19A—H19A109.2C18B—C19B—H19C109.4
C18A—C19A—H19A109.2N3B—C19B—H19D109.4
N3A—C19A—H19B109.2C18B—C19B—H19D109.4
C18A—C19A—H19B109.2H19C—C19B—H19D108.0
H19A—C19A—H19B107.9N3B—C20B—C21B103.47 (13)
N3A—C20A—C21A103.17 (13)N3B—C20B—H20C111.1
N3A—C20A—H20A111.1C21B—C20B—H20C111.1
C21A—C20A—H20A111.1N3B—C20B—H20D111.1
N3A—C20A—H20B111.1C21B—C20B—H20D111.1
C21A—C20A—H20B111.1H20C—C20B—H20D109.0
H20A—C20A—H20B109.1C22B—C21B—C20B103.60 (13)
C22A—C21A—C20A103.56 (14)C22B—C21B—H21C111.0
C22A—C21A—H21A111.0C20B—C21B—H21C111.0
C20A—C21A—H21A111.0C22B—C21B—H21D111.0
C22A—C21A—H21B111.0C20B—C21B—H21D111.0
C20A—C21A—H21B111.0H21C—C21B—H21D109.0
H21A—C21A—H21B109.0C23B—C22B—C21B104.39 (12)
C23A—C22A—C21A104.34 (12)C23B—C22B—H22C110.9
C23A—C22A—H22A110.9C21B—C22B—H22C110.9
C21A—C22A—H22A110.9C23B—C22B—H22D110.9
C23A—C22A—H22B110.9C21B—C22B—H22D110.9
C21A—C22A—H22B110.9H22C—C22B—H22D108.9
H22A—C22A—H22B108.9O3B—C23B—N3B124.75 (14)
O3A—C23A—N3A125.12 (14)O3B—C23B—C22B126.85 (13)
O3A—C23A—C22A126.42 (13)N3B—C23B—C22B108.40 (13)
N3A—C23A—C22A108.45 (13)N4B—C24B—C25B111.00 (13)
N4A—C24A—C25A112.80 (14)N4B—C24B—H24C109.4
N4A—C24A—H24A109.0C25B—C24B—H24C109.4
C25A—C24A—H24A109.0N4B—C24B—H24D109.4
N4A—C24A—H24B109.0C25B—C24B—H24D109.4
C25A—C24A—H24B109.0H24C—C24B—H24D108.0
H24A—C24A—H24B107.8O4B—C25B—C24B111.78 (13)
O4A—C25A—C24A116.21 (15)O4B—C25B—H25C109.3
O4A—C25A—H25A108.2C24B—C25B—H25C109.3
C24A—C25A—H25A108.2O4B—C25B—H25D109.3
O4A—C25A—H25B108.2C24B—C25B—H25D109.3
C24A—C25A—H25B108.2H25C—C25B—H25D107.9
H25A—C25A—H25B107.4O4B—C26B—C27B110.79 (13)
O4A—C26A—C27A115.26 (15)O4B—C26B—H26C109.5
O4A—C26A—H26A108.5C27B—C26B—H26C109.5
C27A—C26A—H26A108.5O4B—C26B—H26D109.5
O4A—C26A—H26B108.5C27B—C26B—H26D109.5
C27A—C26A—H26B108.5H26C—C26B—H26D108.1
H26A—C26A—H26B107.5N4B—C27B—C26B110.81 (13)
N4A—C27A—C26A113.01 (14)N4B—C27B—H27C109.5
N4A—C27A—H27A109.0C26B—C27B—H27C109.5
C26A—C27A—H27A109.0N4B—C27B—H27D109.5
N4A—C27A—H27B109.0C26B—C27B—H27D109.5
C26A—C27A—H27B109.0H27C—C27B—H27D108.1
H27A—C27A—H27B107.8H1WA—O1WA—H2WA103 (2)
C14B—O1B—C15B116.99 (11)H1WB—O1WB—H2WB108 (2)
C7A—N1A—C1A—C2A179.95 (15)C7B—N1B—C1B—C2B−179.34 (15)
C7A—N1A—C1A—C6A−0.31 (15)C7B—N1B—C1B—C6B0.25 (16)
N1A—C1A—C2A—C3A179.21 (14)N1B—C1B—C2B—C3B179.76 (14)
C6A—C1A—C2A—C3A−0.5 (2)C6B—C1B—C2B—C3B0.2 (2)
C1A—C2A—C3A—C4A0.2 (2)C1B—C2B—C3B—C4B−0.7 (2)
C1A—C2A—C3A—C14A−178.72 (13)C1B—C2B—C3B—C14B179.18 (13)
C2A—C3A—C4A—C5A−0.1 (2)C2B—C3B—C4B—C5B0.5 (2)
C14A—C3A—C4A—C5A178.81 (14)C14B—C3B—C4B—C5B−179.44 (14)
C3A—C4A—C5A—C6A0.2 (2)C3B—C4B—C5B—C6B0.3 (2)
C7A—N2A—C6A—C5A179.00 (15)C7B—N2B—C6B—C5B178.63 (15)
C17A—N2A—C6A—C5A9.2 (2)C17B—N2B—C6B—C5B7.7 (2)
C7A—N2A—C6A—C1A−0.55 (15)C7B—N2B—C6B—C1B−0.42 (15)
C17A—N2A—C6A—C1A−170.37 (13)C17B—N2B—C6B—C1B−171.32 (12)
C4A—C5A—C6A—N2A179.96 (15)C4B—C5B—C6B—N2B−179.76 (15)
C4A—C5A—C6A—C1A−0.6 (2)C4B—C5B—C6B—C1B−0.9 (2)
N1A—C1A—C6A—N2A0.54 (16)N1B—C1B—C6B—N2B0.12 (16)
C2A—C1A—C6A—N2A−179.68 (13)C2B—C1B—C6B—N2B179.75 (13)
N1A—C1A—C6A—C5A−179.05 (13)N1B—C1B—C6B—C5B−179.03 (13)
C2A—C1A—C6A—C5A0.7 (2)C2B—C1B—C6B—C5B0.6 (2)
C1A—N1A—C7A—N2A−0.05 (16)C1B—N1B—C7B—N2B−0.53 (16)
C1A—N1A—C7A—C8A178.61 (12)C1B—N1B—C7B—C8B179.32 (13)
C6A—N2A—C7A—N1A0.39 (16)C6B—N2B—C7B—N1B0.62 (16)
C17A—N2A—C7A—N1A169.69 (13)C17B—N2B—C7B—N1B171.07 (13)
C6A—N2A—C7A—C8A−178.23 (13)C6B—N2B—C7B—C8B−179.23 (13)
C17A—N2A—C7A—C8A−8.9 (2)C17B—N2B—C7B—C8B−8.8 (2)
N1A—C7A—C8A—C9A141.68 (15)N1B—C7B—C8B—C9B133.39 (15)
N2A—C7A—C8A—C9A−39.8 (2)N2B—C7B—C8B—C9B−46.8 (2)
N1A—C7A—C8A—C13A−35.0 (2)N1B—C7B—C8B—C13B−43.5 (2)
N2A—C7A—C8A—C13A143.50 (14)N2B—C7B—C8B—C13B136.29 (14)
C13A—C8A—C9A—C10A−1.5 (2)C13B—C8B—C9B—C10B0.3 (2)
C7A—C8A—C9A—C10A−178.16 (13)C7B—C8B—C9B—C10B−176.69 (13)
C8A—C9A—C10A—C11A0.1 (2)C8B—C9B—C10B—C11B−1.0 (2)
C24A—N4A—C11A—C12A−170.35 (15)C9B—C10B—C11B—N4B178.81 (13)
C27A—N4A—C11A—C12A45.7 (2)C9B—C10B—C11B—C12B0.7 (2)
C24A—N4A—C11A—C10A7.4 (2)C24B—N4B—C11B—C10B11.1 (2)
C27A—N4A—C11A—C10A−136.52 (16)C27B—N4B—C11B—C10B145.42 (14)
C9A—C10A—C11A—N4A−176.83 (14)C24B—N4B—C11B—C12B−170.82 (14)
C9A—C10A—C11A—C12A1.0 (2)C27B—N4B—C11B—C12B−36.54 (19)
N4A—C11A—C12A—C13A177.14 (14)C10B—C11B—C12B—C13B0.2 (2)
C10A—C11A—C12A—C13A−0.8 (2)N4B—C11B—C12B—C13B−177.93 (13)
C11A—C12A—C13A—C8A−0.6 (2)C11B—C12B—C13B—C8B−0.9 (2)
C9A—C8A—C13A—C12A1.7 (2)C9B—C8B—C13B—C12B0.6 (2)
C7A—C8A—C13A—C12A178.62 (13)C7B—C8B—C13B—C12B177.74 (13)
C15A—O1A—C14A—O2A−1.4 (2)C15B—O1B—C14B—O2B−1.9 (2)
C15A—O1A—C14A—C3A179.14 (13)C15B—O1B—C14B—C3B176.96 (12)
C2A—C3A—C14A—O2A3.4 (2)C2B—C3B—C14B—O2B8.8 (2)
C4A—C3A—C14A—O2A−175.51 (15)C4B—C3B—C14B—O2B−171.27 (15)
C2A—C3A—C14A—O1A−177.09 (12)C2B—C3B—C14B—O1B−170.03 (13)
C4A—C3A—C14A—O1A4.0 (2)C4B—C3B—C14B—O1B9.9 (2)
C14A—O1A—C15A—C16A−172.75 (14)C14B—O1B—C15B—C16B−162.12 (15)
C6A—N2A—C17A—C18A85.14 (17)C6B—N2B—C17B—C18B74.78 (17)
C7A—N2A—C17A—C18A−82.40 (17)C7B—N2B—C17B—C18B−94.10 (17)
N2A—C17A—C18A—C19A168.93 (12)N2B—C17B—C18B—C19B163.07 (12)
C23A—N3A—C19A—C18A94.52 (17)C23B—N3B—C19B—C18B100.16 (16)
C20A—N3A—C19A—C18A−91.63 (17)C20B—N3B—C19B—C18B−81.86 (17)
C17A—C18A—C19A—N3A−76.53 (16)C17B—C18B—C19B—N3B−66.92 (17)
C23A—N3A—C20A—C21A−17.48 (18)C23B—N3B—C20B—C21B−16.40 (17)
C19A—N3A—C20A—C21A168.04 (14)C19B—N3B—C20B—C21B165.41 (13)
N3A—C20A—C21A—C22A24.94 (18)N3B—C20B—C21B—C22B24.60 (16)
C20A—C21A—C22A—C23A−24.16 (18)C20B—C21B—C22B—C23B−24.49 (16)
C19A—N3A—C23A—O3A−3.0 (2)C19B—N3B—C23B—O3B−0.6 (2)
C20A—N3A—C23A—O3A−177.29 (15)C20B—N3B—C23B—O3B−178.71 (14)
C19A—N3A—C23A—C22A176.23 (13)C19B—N3B—C23B—C22B178.76 (12)
C20A—N3A—C23A—C22A1.95 (18)C20B—N3B—C23B—C22B0.63 (17)
C21A—C22A—C23A—O3A−166.17 (15)C21B—C22B—C23B—O3B−165.12 (14)
C21A—C22A—C23A—N3A14.59 (17)C21B—C22B—C23B—N3B15.55 (16)
C11A—N4A—C24A—C25A170.14 (16)C11B—N4B—C24B—C25B−170.75 (13)
C27A—N4A—C24A—C25A−44.7 (2)C27B—N4B—C24B—C25B52.27 (17)
C26A—O4A—C25A—C24A−46.8 (3)C26B—O4B—C25B—C24B59.34 (17)
N4A—C24A—C25A—O4A45.7 (3)N4B—C24B—C25B—O4B−55.84 (18)
C25A—O4A—C26A—C27A47.3 (2)C25B—O4B—C26B—C27B−60.60 (17)
C11A—N4A—C27A—C26A−168.58 (15)C11B—N4B—C27B—C26B168.84 (13)
C24A—N4A—C27A—C26A45.7 (2)C24B—N4B—C27B—C26B−53.93 (17)
O4A—C26A—C27A—N4A−47.1 (2)O4B—C26B—C27B—N4B58.54 (18)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17A—H17B···O3A0.992.503.2624 (18)133
O1WA—H1WA···O3Bi0.88 (3)2.00 (3)2.8652 (18)168 (2)
O1WA—H2WA···N1Bii0.91 (3)2.01 (3)2.9142 (18)172 (2)
O1WB—H1WB···N1A0.87 (3)2.05 (3)2.9142 (19)172 (2)
O1WB—H2WB···O3Aiii0.83 (3)1.99 (3)2.8218 (18)174 (2)
C15A—H15B···O2Biv0.992.593.412 (2)141
C15B—H15D···O2Aiv0.992.503.227 (2)130
C17A—H17A···O3Bi0.992.443.4334 (18)178
C17B—H17C···O3Ai0.992.363.3274 (18)166
C25A—H25A···O2Bv0.992.373.309 (2)159
C26A—H26B···O4Bvi0.992.543.425 (2)148
C13B—H13B···Cg1iii0.952.873.5419 (15)129
C21B—H21D···Cg20.992.963.8494 (18)150
C24A—H24B···Cg3iii0.992.793.7712 (19)172
C24B—H24D···Cg4vii0.992.673.6357 (17)165
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1; (vi) −x+1, −y, −z−1; (vii) −x, −y, −z.

Experimental details

Crystal data
Chemical formulaC27H32N4O4·H2O
Mr494.58
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)12.2602 (3), 13.7267 (4), 15.3163 (4)
α, β, γ (°)99.357 (1), 93.700 (1), 94.003 (1)
V (Å3)2529.56 (12)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.67 × 0.40 × 0.11
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.942, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		61724, 14611, 10995
Rint0.042
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.152, 1.03
No. of reflections14611
No. of parameters667
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.58, −0.37

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

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1A/N2A/C1A/C6A/C7A, C21B–C26B, C21A–C26A and C21B–C26B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17A—H17B···O3A0.992.503.2624 (18)133
O1WA—H1WA···O3Bi0.88 (3)2.00 (3)2.8652 (18)168 (2)
O1WA—H2WA···N1Bii0.91 (3)2.01 (3)2.9142 (18)172 (2)
O1WB—H1WB···N1A0.87 (3)2.05 (3)2.9142 (19)172 (2)
O1WB—H2WB···O3Aiii0.83 (3)1.99 (3)2.8218 (18)174 (2)
C15A—H15B···O2Biv0.992.593.412 (2)141
C15B—H15D···O2Aiv0.992.503.227 (2)130
C17A—H17A···O3Bi0.992.443.4334 (18)178
C17B—H17C···O3Ai0.992.363.3274 (18)166
C25A—H25A···O2Bv0.992.373.309 (2)159
C26A—H26B···O4Bvi0.992.543.425 (2)148
C13B—H13B···Cg1iii0.952.873.5419 (15)129
C21B—H21D···Cg20.992.963.8494 (18)150
C24A—H24B···Cg3iii0.992.793.7712 (19)172
C24B—H24D···Cg4vii0.992.673.6357 (17)165
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x, y, z−1; (vi) −x+1, −y, −z−1; (vii) −x, −y, −z.
 

Footnotes

‡Thomson Reuters ResearcherID: F-9119-2012.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University grants (Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012) and HiCoE research grant (No. 311.CIPPM.4401005). They also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malaysia for supporting this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages o2967-o2968
https://doi.org/10.1107/S1600536812039268
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